NMT5
canonical SMILES: NCC12CC3(CO[N+](=O)[O-])CC(C2)(CC(C1)(C3)C)C
isomeric SMILES: CC12CC3(C)CC(CN)(C1)CC(CO[N+](=O)[O-])(C2)C3
in ch i key: SYDDVDMTNCXIDJ-UHFFFAOYSA-N
in ch i: InChI=1S/C14H24N2O3/c1-11-3-12(2)5-13(4-11,9-15)8-14(6-11,7-12)10-19-16(17)18/h3-10,15H2,1-2H3
comment: NMT5 is an aminoadamantane nitrate compound. It has been reported as a small molecule that reduces SARS-CoV-2 infection in vitro and in the Syrian hamster COVID-19 model <Reference id=44190/>. NMT5 has a dual-mechanism of action. It simultaneously blocks SARS-CoV-2 ion channels (that are formed by the envelope protein, E, and are implicated in viral assembly, release, and pathogenesis) on the surface of the virion, and it chemically modifies the spike protein (S) to disrupt binding to ACE2 on host cells <Reference id=44190/>. A patent from 2017 reveals that aminoadamantyl nitrate compounds have been proposed for the treatment of CNS disorders, by acting as selective uncompetitive antagonists of activated extrasynaptic NMDA receptors <Reference id=44192/>.
iupac name: [3-(aminomethyl)-5,7-dimethyl-1-adamantyl]methyl nitrate
approved: f
ligand name: NMT5
type: SyntheticOrganicLigand

FUZS-5
in ch i key: CPEAGKYEYPXTSP-XLPZGREQSA-N
in ch i: InChI=1S/C10H14N2O4S/c1-5-3-12(10(15)11-9(5)14)8-2-6(13)7(4-17)16-8/h3,6-8,13,17H,2,4H2,1H3,(H,11,14,15)/t6-,7+,8+/m0/s1
comment: FUZS-5 is a thymidine nucleoside analogue. It has been found to interact with an allosteric site on the SARS-CoV-2 Nsp15 endoribonuclease <Reference id=44177/>.
iupac name: 1-[(2R,4S,5S)-4-hydroxy-5-(sulfanylmethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione
xref: CHEMBL463853
synonym: 5'-Thiothymidine
synonym: 5'-deoxy-5'-thiothymidine
approved: f
ligand name: FUZS-5
type: SyntheticOrganicLigand

LIZA-7
in ch i key: GKEHVJFBPNPCKI-XLPZGREQSA-N
in ch i: InChI=1S/C10H13N5O4/c1-5-4-15(10(18)13-9(5)17)8-2-6(16)7(19-8)3-12-14-11/h4,6-8,16H,2-3H2,1H3,(H,13,17,18)/t6-,7+,8+/m0/s1
comment: LIZA-7 is a thymidine analogue. It has been found to interact with an allosteric site on the SARS-CoV-2 Nsp15 endoribonuclease <Reference id=44177/>.
iupac name: 1-[(2R,4S,5R)-5-(azidomethyl)-4-hydroxyoxolan-2-yl]-5-methylpyrimidine-2,4-dione
xref: CHEMBL102425
synonym: 5'-azido-5'-deoxy-thymidine
approved: f
ligand name: LIZA-7
type: SyntheticOrganicLigand

TTK21
in ch i key: AQJBXYBDNZHZRE-UHFFFAOYSA-N
comment: TTK21 is a small molecule activator of CREB-binding protein (CREBBP) and p300 (EP300) histone acetyltransferases <Reference id=44161/>. It reaches the brain when administered intraperitonealy as a glucose-based carbon nanosphere conjugate. TTK21 induces axon regeneration in in vivo models of spinal injury <Reference id=44163/> and neurodegeneration <Reference id=44164/><Reference id=44162/><Reference id=44161/>.
iupac name: N-[4-chloro-3-(trifluoromethyl)phenyl]-2-propoxybenzamide
synonym: TTK-21
approved: f
ligand name: TTK21
type: SyntheticOrganicLigand

compound 56 [PMID: 36136378]
in ch i key: ATSRNJYTNQHJIO-UHFFFAOYSA-N
in ch i: InChI=1S/C30H27ClN4O5/c1-20-8-10-21(11-9-20)13-15-25(37)32-27-28(31)35(30(40)33(2)29(27)39)17-5-6-22-12-14-24(36)23(18-22)19-34-16-4-3-7-26(34)38/h3-4,7-12,14,16,18,36H,13,15,17,19H2,1-2H3,(H,32,37)
comment: Compound 56 is a novel modulator of the necroptosis executor protein, mixed lineage kinase domain-like protein (MLKL) <Reference id=44154/>. In vitro 56 partially inibits MLKL oligomerization, and reduces translocation of MLKL to the membrane. These two effects are predicted to inhibit the necroptosis pathway.
iupac name: N-(6-Chloro-1-(3-(4-hydroxy-3-((2-oxopyridin-1(2H)-yl)methyl)phenyl)prop-2-yn-1-yl)-3-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)-3-(p-tolyl)propanamide
approved: f
ligand name: compound 56 [PMID: 36136378]
type: SyntheticOrganicLigand

BD-1063
canonical SMILES: CN1CCN(CC1)CCc1ccc(c(c1)Cl)Cl
isomeric SMILES: CN1CCN(CC1)CCc1cc(c(cc1)Cl)Cl
in ch i key: SUIZRDJCBVPASY-UHFFFAOYSA-N
in ch i: InChI=1S/C13H18Cl2N2/c1-16-6-8-17(9-7-16)5-4-11-2-3-12(14)13(15)10-11/h2-3,10H,4-9H2,1H3
comment: BD-1063 is a chemical probe for experimental use. It acts as a sigma non-opioid intracellular receptor 1 (σ1) antagonist <Reference id=38049/>. It also antagonises dopamine receptors.
xref: CHEMBL73824
synonym: BD1063
approved: f
ligand name: BD-1063
type: SyntheticOrganicLigand

GNE-064
in ch i key: FHRKRGDHMCCDEO-LLVKDONJSA-N
in ch i: InChI=1S/C17H21N5O2/c1-11-10-21(7-8-22(11)12(2)23)15-9-14(19-20-17(15)18)13-5-3-4-6-16(13)24/h3-6,9,11,24H,7-8,10H2,1-2H3,(H2,18,20)/t11-/m1/s1
comment: GNE-064 is a selective and orally active small molecule inhibitor of SMARCA4, SMARCA2 and PBRM1 bromodomain-containing proteins, that can be used as a probe to study the functions of these proteins <Reference id=44199/>. Its high solubility suggests that it may be suitable for in vivo studies.
iupac name: 1-[(2R)-4-[3-amino-6-(2-hydroxyphenyl)pyridazin-4-yl]-2-methylpiperazin-1-yl]ethanone
synonym: compound 5 [PMID: 35930799]
synonym: GNE064
approved: f
ligand name: GNE-064
type: SyntheticOrganicLigand

SPH3127
in ch i key: GRTDDIZIUSADLD-CRAIPNDOSA-N
in ch i: InChI=1S/C22H32N6O4/c1-14-5-8-17-19(26-27(20(17)25-14)11-4-9-24-22(30)31-3)15(2)28(16-6-7-16)21(29)18-13-23-10-12-32-18/h5,8,15-16,18,23H,4,6-7,9-13H2,1-3H3,(H,24,30)/t15-,18-/m1/s1
comment: SPH3127 is an orally active direct renin inhibitor <Reference id=44159/>. It induces a more potent antihypertensive effect in in vivo models than the approved renin inhibitor <Ligand id=4812/>.
xref: CHEMBL4110551
synonym: compound 18 [PMID: 35939295]
synonym: SPH-3127
approved: f
ligand name: SPH3127
type: SyntheticOrganicLigand

cefazedone
in ch i key: VTLCNEGVSVJLDN-MLGOLLRUSA-N
comment: Cefazedone is a semisynthetic first generation cephalosporin belonging to the β-lactam class of antibacterial compounds.
iupac name: (6R,7R)-7-[[2-(3,5-dichloro-4-oxopyridin-1-yl)acetyl]amino]-3-[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
xref: CHEMBL2107636
synonym: EMD-30087
synonym: Refosporen®
approved: f
ligand name: cefazedone
type: SyntheticOrganicLigand

cefapirin
in ch i key: UQLLWWBDSUHNEB-CZUORRHYSA-N
in ch i: InChI=1S/C17H17N3O6S2/c1-9(21)26-6-10-7-28-16-13(15(23)20(16)14(10)17(24)25)19-12(22)8-27-11-2-4-18-5-3-11/h2-5,13,16H,6-8H2,1H3,(H,19,22)(H,24,25)/t13-,16-/m1/s1
comment: Cefapirin is a semisynthetic, first generation cephalosporin belonging to the β-lactam class of antibacterial compounds <Reference id=44151/>.
iupac name: (6R,7R)-3-(acetyloxymethyl)-8-oxo-7-[(2-pyridin-4-ylsulfanylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
xref: CHEMBL1599
synonym: cephapirin
synonym: Cefadyl®
synonym: Metricure®
approved: t
ligand name: cefapirin
type: SyntheticOrganicLigand

cefaloglycin
in ch i key: FUBBGQLTSCSAON-PBFPGSCMSA-N
in ch i: InChI=1S/C18H19N3O6S/c1-9(22)27-7-11-8-28-17-13(16(24)21(17)14(11)18(25)26)20-15(23)12(19)10-5-3-2-4-6-10/h2-6,12-13,17H,7-8,19H2,1H3,(H,20,23)(H,25,26)/t12-,13-,17-/m1/s1
comment: Cefaloglycin is a semisynthetic, first generation cephalosporin belonging to the β-lactam class of antibacterial compounds. It is orally absorbed and has activity against both Gram-positive and Gram-negative bacteria <Reference id=44153/>.
iupac name: (6R,7R)-3-(acetyloxymethyl)-7-[[(2R)-2-amino-2-phenylacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
xref: CHEMBL1200971
synonym: cephaloglycin
synonym: Kafocin®
approved: t
ligand name: cefaloglycin
type: SyntheticOrganicLigand

cefatrizine
in ch i key: UOCJDOLVGGIYIQ-PBFPGSCMSA-N
in ch i: InChI=1S/C18H18N6O5S2/c19-12(8-1-3-10(25)4-2-8)15(26)21-13-16(27)24-14(18(28)29)9(7-31-17(13)24)6-30-11-5-20-23-22-11/h1-5,12-13,17,25H,6-7,19H2,(H,21,26)(H,28,29)(H,20,22,23)/t12-,13-,17-/m1/s1
comment: Cefatrizine is a semisynthetic first generation cephalosporin belonging to the β-lactam class of antibacterial compounds.
iupac name: (6R,7R)-7-[[(2R)-2-amino-2-(4-hydroxyphenyl)acetyl]amino]-8-oxo-3-(2H-triazol-4-ylsulfanylmethyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
xref: CHEMBL1095284
synonym: BL-S640
synonym: BL-S 640
approved: f
ligand name: cefatrizine
type: SyntheticOrganicLigand

cefacetrile
in ch i key: RRYMAQUWDLIUPV-BXKDBHETSA-N
in ch i: InChI=1S/C13H13N3O6S/c1-6(17)22-4-7-5-23-12-9(15-8(18)2-3-14)11(19)16(12)10(7)13(20)21/h9,12H,2,4-5H2,1H3,(H,15,18)(H,20,21)/t9-,12-/m1/s1
comment: Cefacetrile is a first generation cephalosporin belonging to the β-lactam class of antibacterial compounds.
iupac name: (6R,7R)-3-(acetyloxymethyl)-7-[(2-cyanoacetyl)amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
xref: CHEMBL2110602
synonym: Vetrimast®
synonym: Celospor®
synonym: cephacetrile
synonym: cephacetril
approved: f
ligand name: cefacetrile
type: SyntheticOrganicLigand

AMG28
canonical SMILES: Nc1ncc2c(n1)c1c(CCC2)[nH]c2c1cc(C#CC(O)(C)C)cc2
isomeric SMILES: CC(C)(C#Cc1cc2c(cc1)[nH]c1c2c2c(CCC1)cnc(n2)N)O
in ch i key: DGLFSNZWRYADFC-UHFFFAOYSA-N
in ch i: InChI=1S/C20H20N4O/c1-20(2,25)9-8-12-6-7-15-14(10-12)17-16(23-15)5-3-4-13-11-22-19(21)24-18(13)17/h6-7,10-11,23,25H,3-5H2,1-2H3,(H2,21,22,24)
comment: AMG28 is a small molecule multi-kinase inhibitor, with activity against NF-κB inducing kinase (NIK; MAP3K14), Tau tubulin kinase 1 (TTBK1), and the lipid modifying phosphoinositide kinase, FYVE-type zinc finger containing (PIKFYVE), amongst others <Reference id=44124/>. It is one of the kinase inhibitors claimed in Amgen patent WO2009158011A1 <Reference id=44125/>.
xref: CHEMBL2334586
synonym: inhibitor 3 [PMID: 33944571]
synonym: example 240 [WO2009158011A1]
approved: f
ligand name: AMG28
type: SyntheticOrganicLigand

compound 17 [PMID: 36111834]
canonical SMILES: CN(CC#Cc1ccc2c(c1)c1c([nH]2)CCCc2c1nc(N)nc2)C
in ch i key: DORZPJWJOBMQKC-UHFFFAOYSA-N
in ch i: InChI=1S/C20H21N5/c1-25(2)10-4-5-13-8-9-16-15(11-13)18-17(23-16)7-3-6-14-12-22-20(21)24-19(14)18/h8-9,11-12,23H,3,6-7,10H2,1-2H3,(H2,21,22,24)
comment: This is a small molecule that can be used to examine the effects of phosphatidylinositol-3-phosphate 5-kinase (PIKfyve) inhibition on the viral lifecycle <Reference id=44123/>. Compound 17 is selective for PIKfyve, and it has been demonstrated to disrupt both entry and replication of β-coronaviruses in vitro. Its core structure was derived from the non-selective kinase inhibitor <Ligand id=12186/>.
iupac name: 11-(3-(Dimethylamino)prop-1-yn-1-yl)-5,6,7,8-tetrahydropyrimido[4′,5′:3,4]cyclohepta[1,2-b]indol-2-amine
approved: f
ligand name: compound 17 [PMID: 36111834]
type: SyntheticOrganicLigand

CC-99677
in ch i key: PYOQIOLRFIRRSO-LLVKDONJSA-N
comment: CC-99677 is an oral, irreversible, covalent MAPK-activated protein kinase-2 (MK2) inhibitor <Reference id=44070/>. It interacts with the sulphur atom of cysteine 140 in MK2's ATP binding site. CC-99677 is being explored as an alternative to direct p38 inhibitors, for potential to treat autoinflammatory diseases.
synonym: CC99677
approved: f
ligand name: CC-99677
type: SyntheticOrganicLigand

compound 22 [WO2019141694A1]
in ch i key: LGILUCRVDGGDMI-NRFANRHFSA-N
in ch i: InChI=1S/C33H39N7O3/c1-20-11-12-24(16-26(20)32(42)39(7)21(2)19-41)29-22(3)37-40-28(17-27(33(4,5)43)36-31(29)40)35-18-23-9-8-10-25(15-23)30-34-13-14-38(30)6/h8-17,21,35,41,43H,18-19H2,1-7H3/t21-/m0/s1
comment: Compound 22 is a phosphatidylinositol 4-kinase beta (PI4KIIIβ) inhibitor that was designed by GSK as an inhalation drug that's proposed to reduce the severity of viral lung infections that often exacerbate COPD symptoms. Its chemical structure is claimed in patent WO2019141694A1 <Reference id=44115/>. PI4KIIIβ activity regulates pools of phosphatidylinositol-4 phosphate (PI4P) that are crucial for the integrity of cell membranes, and it is principally active within the Golgi network. Experimental evidence indicates that PI4KIIIβ is involved in the genomic replication of a range of RNA viruses (e.g. human rhinovirus, enteroviruses 68 and 71, poliovirus, coxsackie virus, hepatitis C virus, bovine kobuvirus, aichi virus and rubella). It was also reported to be required for spike protein mediated cell entry of the 2002/2003 version of SARS coronavirus <Reference id=44116/>. These findings led to the emergence of PI4KB as a potential target for the development of broad spectrum antiviral agents. This structure was disclosed as 'compound 30' during a 'first disclosures' session at the XXVll EFMC International Symposium on Medicinal Chemistry in September 2022.
approved: f
ligand name: compound 22 [WO2019141694A1]
type: SyntheticOrganicLigand

KC-180-2
in ch i key: KUPDBUBFYCYCNJ-UHFFFAOYSA-N
in ch i: InChI=1S/C23H23N3O/c27-23(25-16-18-5-2-1-3-6-18)15-21-10-7-20(17-24-21)19-8-11-22(12-9-19)26-13-4-14-26/h1-3,5-12,17H,4,13-16H2,(H,25,27)
comment: KC-180-2 is a dual action tubulin polymerisation inhibitor and Src kinase inhibitor that was developed as a refined derivative of the anti-cancer agent <Ligand id=7957/> (KX2-391) <Reference id=44105/>. Destabilisation of tubulin polymers is the primary mechanism that underlies KC-180-2's effects on cell cycle arrest in cancer cells. KC-180-2 occupies the same non-ATP substrate binding pocket within Src as KX2-391.
approved: f
ligand name: KC-180-2
type: SyntheticOrganicLigand

LY3502970
in ch i key: USUWIEBBBWHKNI-KHIFEHGGSA-N
comment: LY3502970 is an oral, nonpeptide glucagon-like peptide-1 receptor (GLP-1R) agonist that was developed as a potential antidiabetic medication <Reference id=44102/>. It is a partial agonist (relative to native GLP-1), that biases GLP-1R signalling towards G protein activation and is devoid of β-arrestin recruitment activity.
iupac name: 3-[(1S,2S)-1-[5-[(4S)-2,2-dimethyloxan-4-yl]-2-[(4S)-2-(4-fluoro-3,5-dimethylphenyl)-3-[3-(4-fluoro-1-methylindazol-5-yl)-2-oxoimidazol-1-yl]-4-methyl-6,7-dihydro-4H-pyrazolo[4,3-c]pyridine-5-carbonyl]indol-1-yl]-2-methylcyclopropyl]-4H-1,2,4-oxadiazol-5-one
xref: CHEMBL4446782
synonym: LY-3502970
synonym: OWL833
approved: f
ligand name: LY3502970
type: SyntheticOrganicLigand

NIC-0102
in ch i key: QTRFWSIBLJYXFJ-ROUUACIJSA-N
comment: NIC-0102 is a small molecule proteasome inhibitor <Reference id=44101/>. It selectively promotes polyubiquitination and proteasome-mediated degradation of NLRP3 protein. The resulting effect is a reduction in the amount of NLRP3 available for NLRP3 inflammasome assembly. In addition, NIC-0102 appears to disrupt the NLRP3-ASC interaction which is crucial for ASC oligomerization and inflammasome complex formation. Although NIC-0102 is structurally related to <Ligand id=6391/>, the mechanism by which it inhibits NLRP3-dependent IL-1β secretion is different.
synonym: compound 27 [PMID: 36063115]
approved: f
ligand name: NIC-0102
type: SyntheticOrganicLigand

selnoflast
in ch i key: OHIFQOUPTWBQLE-UHFFFAOYSA-N
in ch i: InChI=1S/C20H29N3O3S/c1-2-23-11-9-16(10-12-23)27(25,26)22-20(24)21-19-17-7-3-5-14(17)13-15-6-4-8-18(15)19/h13,16H,2-12H2,1H3,(H2,21,22,24)
comment: Selnoflast (RG6418) is a small molecule inhibitor of NLRP3 inflammasome activation <Reference id=44100/>. It is structurally related to <Ligand id=8228/> and <Ligand id=12172/> (MCC7840). Inhibition of NLRP3 inflammasome activity has anti-inflammatory action that can be applied for the treatment of chronic inflammatory diseases.
iupac name: 1-(1-ethylpiperidin-4-yl)sulfonyl-3-(1,2,3,5,6,7-hexahydro-s-indacen-4-yl)urea
synonym: RG6418
synonym: RG-6418
synonym: Example 6 [WO2019008025A1]
approved: f
ligand name: selnoflast
type: SyntheticOrganicLigand

enmetazobactam
in ch i key: HFZITXBUTWITPT-YWVKMMECSA-N
in ch i: InChI=1S/C11H14N4O5S/c1-11(6-14-4-3-13(2)12-14)9(10(17)18)15-7(16)5-8(15)21(11,19)20/h3-4,8-9H,5-6H2,1-2H3/t8-,9+,11+/m1/s1
comment: Enmetazobactam is an extended-spectrum β-lactamase inhibitor. It is an N-methylated <Ligand id=10789/> derivative, under clinical development for use alongside β-lactam-containing antibacterial compounds to reduce their lactamase-induced degradation.
iupac name: (2S,3S,5R)-3-methyl-3-[(3-methyltriazol-3-ium-1-yl)methyl]-4,4,7-trioxo-4λ6-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
xref: CHEMBL4458276
synonym: AAI101
synonym: AAI-101
synonym: OCID-5090
approved: f
ligand name: enmetazobactam
type: SyntheticOrganicLigand

compound 35m [PMID: 36073117]
in ch i key: ZNRZSMMDQXGEGA-UHFFFAOYSA-N
in ch i: InChI=1S/C23H22N4O/c1-2-25-26-23(28)20-9-7-17(8-10-20)16-27-21-6-4-3-5-18(21)11-12-19-13-14-24-15-22(19)27/h3-15,25H,2,16H2,1H3,(H,26,28)
comment: This compound is a novel, selective inhibitor of histone deacetylase 6 (HDAC6) with anti-inflammatory potential <Reference id=44109/>. Orally administered 35m inhibited NLRP3 inflammasome activation and IL-1β release in vivo.
approved: f
ligand name: compound 35m [PMID: 36073117]
type: SyntheticOrganicLigand

doripenem
in ch i key: AVAACINZEOAHHE-VFZPANTDSA-N
comment: Doripenem is a parenterally delivered, carbapenem antibacterial compound. It is a semi-synthetic derivative of thienamycin and was developed by the Shionogi Research Laboratories (Osaka, Japan) <Reference id=44117/>.
iupac name: (4R,5S,6S)-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-3-[(3S,5S)-5-[(sulfamoylamino)methyl]pyrrolidin-3-yl]sulfanyl-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
xref: CHEMBL491571
synonym: S 4661
synonym: S-4661
synonym: Doribax®
synonym: compound 1m [PMID: 8621362]
approved: t
ligand name: doripenem
type: SyntheticOrganicLigand

cefaloridine
in ch i key: CZTQZXZIADLWOZ-CRAIPNDOSA-N
in ch i: InChI=1S/C19H17N3O4S2/c23-14(9-13-5-4-8-27-13)20-15-17(24)22-16(19(25)26)12(11-28-18(15)22)10-21-6-2-1-3-7-21/h1-8,15,18H,9-11H2,(H-,20,23,25,26)/t15-,18-/m1/s1
comment: Cefaloridine (also known as cephaloridine) is a semisynthetic, first generation cephalosporin belonging to the β-lactam class of antibacterial compounds. It is a derivative of cephalosporin C and demonstrates broad-spectrum antibacterial activity against Gram-positive and Gram-negative bacteria <Reference id=44143/>.
iupac name: (6R,7R)-8-oxo-3-(pyridin-1-ium-1-ylmethyl)-7-[(2-thiophen-2-ylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
xref: CHEMBL316157
synonym: cephaloridine
synonym: ceporin
approved: f
ligand name: cefaloridine
type: SyntheticOrganicLigand

panipenem
in ch i key: TYMABNNERDVXID-DLYFRVTGSA-N
in ch i: InChI=1S/C15H21N3O4S/c1-7(19)12-10-5-11(13(15(21)22)18(10)14(12)20)23-9-3-4-17(6-9)8(2)16/h7,9-10,12,16,19H,3-6H2,1-2H3,(H,21,22)/t7-,9+,10-,12-/m1/s1
comment: Panipenem is a carbapenem antibacterial compound developed by Daiichi Sankyo <Reference id=44118/>.
iupac name: (5R,6S)-3-[(3S)-1-ethanimidoylpyrrolidin-3-yl]sulfanyl-6-[(1R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
xref: CHEMBL339323
synonym: RS-533
synonym: RS 533
synonym: CS-533
synonym: CS 533
synonym: Carbenin® (panipenem + betamipron)
approved: t
ligand name: panipenem
type: SyntheticOrganicLigand

emlenoflast
in ch i key: MTOUOUSKXWSTAX-UHFFFAOYSA-N
in ch i: InChI=1S/C19H24N4O3S/c1-12(2)23-10-9-17(21-23)27(25,26)22-19(24)20-18-15-7-3-5-13(15)11-14-6-4-8-16(14)18/h9-12H,3-8H2,1-2H3,(H2,20,22,24)
comment: Emlenoflast (MCC7840 <Reference id=44099/>; formerly IZD 174) is one of a growing number of NLRP3 inflammasome inhibitors that have been developed for anti-inflammatory potential <Reference id=44097/>. It was developed by Inflazome (acquired by Roche in 2020) as an orally bioavailable drug that is able to cross the blood-brain barrier.
iupac name: 1-(1,2,3,5,6,7-hexahydro-s-indacen-4-yl)-3-(1-propan-2-ylpyrazol-3-yl)sulfonylurea
xref: CHEMBL4650350
synonym: MCC7840
synonym: MCC-7840
synonym: Inzomelid
approved: f
ligand name: emlenoflast
type: SyntheticOrganicLigand

compound 8l [PMID: 36053746]
in ch i key: JEESDVDVWGRNFE-UHFFFAOYSA-N
in ch i: InChI=1S/C23H22Cl2N4O/c1-13-27-21-12-26-20-4-3-14(15-10-18(24)23(30)19(25)11-15)9-17(20)22(21)29(13)16-5-7-28(2)8-6-16/h3-4,9-12,16,30H,5-8H2,1-2H3
comment: This compound acts as a pan-Janus kinase (JAK) inhibitor and has effects across a range of proinflammatory signalling pathways, including simultaneous suppression of JAK/STAT and NF-κB signalling <Reference id=44088/>. 8l has strong anti-inflammatory activity in in vivo models of inflammatory bowel disease.
approved: f
ligand name: compound 8l [PMID: 36053746]
type: SyntheticOrganicLigand

UCM-1306
canonical SMILES: FCOc1ccccc1c1ccc(cc1)S(=O)(=N)C
isomeric SMILES: N=S(=O)(c1ccc(c2ccccc2OCF)cc1)C
in ch i key: VCSBOASGFYJGGT-UHFFFAOYSA-N
in ch i: InChI=1S/C14H14FNO2S/c1-19(16,17)12-8-6-11(7-9-12)13-4-2-3-5-14(13)18-10-15/h2-9,16H,10H2,1H3
comment: UCM-1306 is a positive allosteric modulator (PAM) of the human dopamine D1 receptor <Reference id=44087/>. It increases the affinity of the receptor for dopamine (i.e. the orthosteric agonist), increases the maximal effect of dopamine but is inactive in the absence of dopamine. UCM-1306, which is orally bioavailable, is being investigated as a mechanism to improve the therapeutic effect of L-DOPA in the treatment of Parkinson's disease
synonym: compound 26 [PMID: 36044544]
synonym: UCM1306
approved: f
ligand name: UCM-1306
type: SyntheticOrganicLigand

IHMT-MST1-58
in ch i key: FWEIAKDAIDQPRK-UHFFFAOYSA-N
in ch i: InChI=1S/C21H22N6O3S/c1-13-6-4-5-7-16(13)18-20(28)26(2)17-12-23-21(25-19(17)27(18)3)24-14-8-10-15(11-9-14)31(22,29)30/h4-12,18H,1-3H3,(H2,22,29,30)(H,23,24,25)
comment: IHMT-MST1-58 is a potent and selective serine/threonine kinase 4 (STK4; MST1) inhibitor <Reference id=44071/>. It is suitable as a pharmacological probe of STK4's roles in physiology and pathology, and may also be considered as a anti-diabetes clinical candidate.
iupac name: 4-[[5,8-dimethyl-7-(2-methylphenyl)-6-oxo-7H-pteridin-2-yl]amino]benzenesulfonamide
synonym: compound 19 [PMID: 36037148]
approved: f
ligand name: IHMT-MST1-58
type: SyntheticOrganicLigand

PJ34
in ch i key: UYJZZVDLGDDTCL-UHFFFAOYSA-N
in ch i: InChI=1S/C17H17N3O2/c1-20(2)10-16(21)18-11-7-8-15-14(9-11)12-5-3-4-6-13(12)17(22)19-15/h3-9H,10H2,1-2H3,(H,18,21)(H,19,22)
comment: PJ34 is a poly(ADP-ribose) polymerase-1 (PARP-1) inhibitor <Reference id=41091/><Reference id=41092/>. It is a tool compound that is active in vitro and in vivo. PARP-1 inhibitors downregulate multiple pathways of inflammation and tissue injury, and a number of potent inhibitors have been developed for anti-cancer potential..
iupac name: 2-(dimethylamino)-N-(6-oxo-5H-phenanthridin-2-yl)acetamide
xref: CHEMBL372303
synonym: PJ-34
approved: f
ligand name: PJ34
type: SyntheticOrganicLigand

NNMT inhibitor 14 [PMID: 35904556]
in ch i key: LJMIMBZGIMDSPE-BHDXBOSCSA-N
in ch i: InChI=1S/C34H34ClN7O/c1-20-4-9-30-24(10-20)14-31(40(30)18-23-5-7-27(35)8-6-23)32-15-29(42-28(16-36)12-22(3)39-42)19-41(32)34(43)26-13-25-11-21(2)38-33(25)37-17-26/h4-14,17,29,32H,15-16,18-19,36H2,1-3H3,(H,37,38)/t29-,32+/m0/s1
comment: This is a small molecule inhibitor of nicotinamide N-methyltransferase (NNMT) <Reference id=44069/>. It is suitable for biochemical and cellular assays.
iupac name: 1-{1-[(3S,5R)-5-{1-[(4-chlorophenyl)methyl]-5-methyl-1H-indol-2-yl}-1-{2-methyl-1H-pyrrolo[2,3-b]pyridine-5-carbonyl}pyrrolidin-3-yl]-3-methyl-1H-pyrazol-5-yl}methanamine
approved: f
ligand name: NNMT inhibitor 14 [PMID: 35904556]
type: SyntheticOrganicLigand

CHF-6366
in ch i key: YWSIONULMMKTSJ-UZGNFBRWSA-N
in ch i: InChI=1S/C42H48N6O8/c1-47-30(23-34(46-47)41(52)54-21-6-5-18-43-24-36(50)32-12-14-35(49)40-33(32)13-15-38(51)44-40)26-55-31-11-7-10-29(22-31)39(28-8-3-2-4-9-28)45-42(53)56-37-25-48-19-16-27(37)17-20-48/h2-4,7-15,22-23,27,36-37,39,43,49-50H,5-6,16-21,24-26H2,1H3,(H,44,51)(H,45,53)/t36-,37-,39-/m0/s1
comment: CHF-6366 is a dual pharmacology muscarinic receptor antagonist and β2 receptor agonist (MABA) <Reference id=44066/>. It was designed to be an inhaled agent for the treatment of respiratory diseases that provides sustained exposure in the lung, but which is rapidly metabolised and eliminated from the systemic circulation.
iupac name: 4-[[(2R)-2-hydroxy-2-(8-hydroxy-2-oxo-1H-quinolin-5-yl)ethyl]amino]butyl 5-[[3-[(S)-[[(3R)-1-azabicyclo[2.2.2]octan-3-yl]oxycarbonylamino]-phenylmethyl]phenoxy]methyl]-1-methylpyrazole-3-carboxylate
synonym: compound 29 [PMID: 35901125]
synonym: CHF6366
approved: f
ligand name: CHF-6366
type: SyntheticOrganicLigand

BI-4142
in ch i key: GBSWEJRAVNWKCB-UHFFFAOYSA-N
in ch i: InChI=1S/C25H25N9O/c1-16-11-17(3-6-22(16)35-18-4-5-21-19(12-18)30-15-33(21)2)31-24-23-20(28-14-29-24)13-27-25(32-23)34-9-7-26-8-10-34/h3-6,11-15,26H,7-10H2,1-2H3,(H,28,29,31)
comment: BI-4142 is an oral HER2 selective inhibitor <Reference id=44064/>. It inhibits proliferation of Ba/F3 cancer cells with wild-type and activating exon 20 mutation HER2YVMA. EGFR signalling via the EGFR receptor is not altered by BI-4142. BI-4142 is being developed for potential to treat advanced non-small cell lung cancer with oncogenic alterations in Exon 20 of the ERBB2 gene.
iupac name: N-[3-methyl-4-(1-methylbenzimidazol-5-yl)oxyphenyl]-6-piperazin-1-ylpyrimido[5,4-d]pyrimidin-4-amine
synonym: BI4142
synonym: compound 8 [PMID: 35883003]
synonym: example L-1 [WO2021156178A1]
approved: f
ligand name: BI-4142
type: SyntheticOrganicLigand

ribostamycin
in ch i key: NSKGQURZWSPSBC-VVPCINPTSA-N
in ch i: InChI=1S/C17H34N4O10/c18-2-6-10(24)12(26)8(21)16(28-6)30-14-5(20)1-4(19)9(23)15(14)31-17-13(27)11(25)7(3-22)29-17/h4-17,22-27H,1-3,18-21H2/t4-,5+,6-,7-,8-,9+,10-,11-,12-,13-,14-,15-,16-,17+/m1/s1
comment: Ribostamycin belongs to the aminoglycoside class of antibacterial compounds and was originally isolated from Streptomyces ribosidificus <Reference id=44061/>.
iupac name: (2R,3S,4R,5R,6R)-5-amino-2-(aminomethyl)-6-[(1R,2R,3S,4R,6S)-4,6-diamino-2-[(2S,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-3-hydroxycyclohexyl]oxyoxane-3,4-diol
xref: CHEMBL221572
synonym: SF-733
approved: f
ligand name: ribostamycin
type: NaturalProductLigand

dihydrostreptomycin
in ch i key: ASXBYYWOLISCLQ-HZYVHMACSA-N
in ch i: InChI=1S/C21H41N7O12/c1-5-21(36,4-30)16(40-17-9(26-2)13(34)10(31)6(3-29)38-17)18(37-5)39-15-8(28-20(24)25)11(32)7(27-19(22)23)12(33)14(15)35/h5-18,26,29-36H,3-4H2,1-2H3,(H4,22,23,27)(H4,24,25,28)/t5-,6-,7+,8-,9-,10-,11+,12-,13-,14+,15+,16-,17-,18-,21+/m0/s1
comment: Dihydrostreptomycin is an aminoglycoside antibacterial drug and a derivative of <Ligand id=10923/> <Reference id=44255/>.
iupac name: 2-[(1R,2R,3S,4R,5R,6S)-3-(diaminomethylideneamino)-4-[(2R,3R,4R,5S)-3-[(2S,3S,4S,5R,6S)-4,5-dihydroxy-6-(hydroxymethyl)-3-(methylamino)oxan-2-yl]oxy-4-hydroxy-4-(hydroxymethyl)-5-methyloxolan-2-yl]oxy-2,5,6-trihydroxycyclohexyl]guanidine
xref: CHEMBL1950576
approved: t
ligand name: dihydrostreptomycin
type: SyntheticOrganicLigand

micronomicin
in ch i key: DNYGXMICFMACRA-XHEDQWPISA-N
in ch i: InChI=1S/C20H41N5O7/c1-20(28)8-29-19(14(27)17(20)25-3)32-16-12(23)6-11(22)15(13(16)26)31-18-10(21)5-4-9(30-18)7-24-2/h9-19,24-28H,4-8,21-23H2,1-3H3/t9-,10+,11-,12+,13-,14+,15+,16-,17+,18+,19+,20-/m0/s1
comment: Micronomicin belongs to the aminoglycoside class of antibacterial compounds and was originally isolated from Micromonospora sagamiensis <Reference id=44062/>. It is an analogue of <Ligand id=2427/>.
iupac name: (2R,3R,4R,5R)-2-[(1S,2S,3R,4S,6R)-4,6-diamino-3-[(2R,3R,6S)-3-amino-6-(methylaminomethyl)oxan-2-yl]oxy-2-hydroxycyclohexyl]oxy-5-methyl-4-(methylamino)oxane-3,5-diol
xref: CHEMBL373081
synonym: gentamicin C2b
synonym: XK-62-2
synonym: Luxomicina®
synonym: Sagamicin®
approved: t
ligand name: micronomicin
type: NaturalProductLigand

PF-07258669
in ch i key: PARGFYLSRQUWHR-BZQUYTCOSA-N
in ch i: InChI=1S/C25H27FN6O2/c1-15(18-12-21(34-3)29-13-20(18)26)24(33)32-10-7-25(14-32)6-5-17-11-19(16(2)30-22(17)31-25)23-27-8-4-9-28-23/h4,8-9,11-13,15H,5-7,10,14H2,1-3H3,(H,30,31)/t15-,25+/m1/s1
comment: PF-07258669's chemical structure was revealed during the first disclosures session at the 2022 ACS meeting in Chicago. This is Pfizer's melanocortin 4 receptor (MC4R) antagonist. Blocking MC4R activation is proposed as a mechanism to increase weight gain, and Pfizer intend this agent to be used to treat geriatric anorexia.
iupac name: (2R)-2-(5-fluoro-2-methoxypyridin-4-yl)-1-[(2S)-7-methyl-6-(pyrimidin-2-yl)-3,4-dihydro-1H-spiro[1,8-naphthyridine-2,3'-pyrrolidin]-1'-yl]propan-1-one
approved: f
ligand name: PF-07258669
type: SyntheticOrganicLigand

GLPG3970
in ch i key: XASOHFCUIQARJT-UHFFFAOYSA-N
in ch i: InChI=1S/C25H27F3N4O4/c1-34-21-13-18(12-17-2-4-31(16-25(26,27)28)24(33)23(17)21)20-15-29-22-14-19(3-5-32(20)22)36-11-8-30-6-9-35-10-7-30/h3,5,12-15H,2,4,6-11,16H2,1H3
comment: GLPG3970's chemical structure was revealed during the first disclosures session at the 2022 ACS meeting in Chicago. This is Galapagos' oral, salt inducible kinase 2 and 3 (SIK2/3) inhibitor that was proposed for treating inflammatory diseases.
iupac name: 8-methoxy-6-[7-(2-morpholin-4-ylethoxy)imidazo[1,2-a]pyridin-3-yl]-2-(2,2,2-trifluoroethyl)-3,4-dihydroisoquinolin-1-one
synonym: compound 88 [WO2019238424A1]
synonym: GLPG-3970
approved: f
ligand name: GLPG3970
type: SyntheticOrganicLigand

onfasprodil
in ch i key: NEFQLCKWVRZEJA-ZWVKXQFTSA-N
in ch i: InChI=1S/C20H23FN2O3/c21-17-3-1-2-4-20(17)26-16-7-13-10-23(11-14(13)8-16)12-19(25)18-6-5-15(24)9-22-18/h1-6,9,13-14,16,19,24-25H,7-8,10-12H2/t13-,14+,16?,19-/m0/s1
comment: Onfasprodil was identified from WHO proposed INN list 126 (Jan 2022) as a N-methyl-D-aspartate (NMDA) receptor antagonist. It acts as a negative allosteric modulator of the glutamate ionotropic receptor NMDA type subunit 2B (GRIN2B; GluN2B or NR2B) and is proposed as an intravenous, rapid onset antidepressant. Onfasprodil's chemical structure is claimed in patent US10239835B2 <Reference id=44056/>. We predict that is onfasprodil Novartis' Phase 2 clinical lead MIJ821, although name-to-structure has not been disclosed.
iupac name: 6-[(1S)-2-[(3aR,6aS)-5-(2-fluorophenoxy)-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrol-2-yl]-1-hydroxyethyl]pyridin-3-ol
approved: f
ligand name: onfasprodil
type: SyntheticOrganicLigand

NDI-034858
in ch i key: BWINBHTTZLVXGT-NVXWUHKLSA-N
in ch i: InChI=1S/C23H24N8O3/c1-24-20-12-18(27-16-6-5-11-30(23(16)33)19-7-3-4-10-25-19)29-21-14(13-26-31(20)21)22(32)28-15-8-9-17(15)34-2/h3-7,10-13,15,17,24H,8-9H2,1-2H3,(H,27,29)(H,28,32)/t15-,17-/m1/s1
comment: NDI-034858 is an orally bioavailable TYK2-selective inhibitor. Its chemical structure was revealed during the first disclosures session at the 2022 ACS meeting in Chicago. NDI-034858 is one of the compounds (I-908) claimed in patent US20190256519A1 <Reference id=44054/>.
iupac name: N-[(1R,2R)-2-methoxycyclobutyl]-7-(methylamino)-5-[(2-oxo-1-pyridin-2-ylpyridin-3-yl)amino]pyrazolo[1,5-a]pyrimidine-3-carboxamide
synonym: NDI034858
synonym: compound I-908 [US20190256519A1]
approved: f
ligand name: NDI-034858
type: SyntheticOrganicLigand

mitiperstat
in ch i key: BHKKSKOHRFHHIN-MRVPVSSYSA-N
in ch i: InChI=1S/C15H15ClN4OS/c1-8(17)11-6-10(16)3-2-9(11)7-20-12-4-5-18-13(12)14(21)19-15(20)22/h2-6,8,18H,7,17H2,1H3,(H,19,21,22)/t8-/m1/s1
comment: Mitiperstat (AZD4831) is an irreversible and selective myeloperoxidase (MPO) inhibitor that was developed by AstraZeneca <Reference id=44059/><Reference id=44059/>. It is intended as a treament of patients suffering from heart failure with preserved ejection fraction (HFpEF).
iupac name: 1-[[2-[(1R)-1-aminoethyl]-4-chlorophenyl]methyl]-2-sulfanylidene-5H-pyrrolo[3,2-d]pyrimidin-4-one
synonym: compound 16 [PMID: 36005476]
synonym: AZD4831
synonym: AZD-4831
approved: f
ligand name: mitiperstat
type: SyntheticOrganicLigand

FLX475
in ch i key: AKSVALRPYDVQBS-CABCVRRESA-N
comment: FLX475 is an orally bioavailable CCR4 antagonist that was developed by RAPT Therapeutics, and is one of the structures claimed in patent WO2018022992A1 <Reference id=44051/>. Antagonising CCR4 is proposed to activate the immune response against Epstein-Barr Virus (EBV)-positive tumours <Reference id=44050/>. FLX475's chemical structure was revealed during the first disclosures session at the 2022 ACS meeting in Chicago.
iupac name: 2-[(3R)-3-[1-[1-[(1R)-1-(2,4-dichlorophenyl)ethyl]-3-(trifluoromethyl)pyrazolo[3,4-b]pyrazin-6-yl]azetidin-3-yl]piperidin-1-yl]ethanol
synonym: FLX-475
synonym: example 43 [WO2018022992A1]
approved: f
ligand name: FLX475
type: SyntheticOrganicLigand

MRGPRX2 antagonist 17
in ch i key: UOCITXUZOXOHLH-WMLDXEAASA-N
in ch i: InChI=1S/C23H21F4N5O3/c1-14(31-9-6-23(26,27)17(13-31)15-4-7-32(34)8-5-15)22(33)30-20-11-29-21(12-28-20)35-19-3-2-16(24)10-18(19)25/h2-5,7-8,10-12,14,17H,6,9,13H2,1H3,(H,28,30,33)/t14-,17+/m0/s1
comment: The chemical structure for this MRGPRX2 antagonist was revealed during the first disclosures session at the 2022 ACS meeting in Chicago. The orphan MRGPRX GPCRs are being investigated as potential drug targets for mast cell-mediated immune diseases <Reference id=44046/><Reference id=44047/><Reference id=44048/><Reference id=44049/>.
approved: f
ligand name: MRGPRX2 antagonist 17
type: SyntheticOrganicLigand

APD668
in ch i key: XTRUQJBVQBUKSQ-UHFFFAOYSA-N
in ch i: InChI=1S/C21H24FN5O5S/c1-13(2)31-21(28)26-8-6-14(7-9-26)32-20-16-11-25-27(19(16)23-12-24-20)18-5-4-15(10-17(18)22)33(3,29)30/h4-5,10-14H,6-9H2,1-3H3
comment: APD668 (also known as JNJ-28630368) is a synthetic small molecule agonist of the orphan G protein-coupled receptor GPR119 <Reference id=44043/><Reference id=18791/>. Its in vitro profile and in vivo actions as a GLP-1 secretagogue, reducing triglyceride uptake and hepatic lipogenesis suggests the potential of GPR119 agonists for the treatment of dyslipidemia and non-alcoholic steatohepatitis. However, clinical development of both this compound and the structurally related lead <Ligand id=5727/> has been terminated.
iupac name: propan-2-yl 4-[1-(2-fluoro-4-methylsulfonylphenyl)pyrazolo[3,4-d]pyrimidin-4-yl]oxypiperidine-1-carboxylate
xref: CHEMBL1775179
synonym: APD-668
synonym: JNJ-28630368
synonym: JNJ28630368
synonym: compound A129 [WO2005007658A2]
synonym: compound 3k [PMID: 21444206]
approved: f
ligand name: APD668
type: SyntheticOrganicLigand

LJ-4517
isomeric SMILES: O[C@H]1[C@@H](O)[C@H](n2c3nc(C#CCCCC)nc(N)c3nc2c2cccs2)OC1
in ch i key: MUHXGASCCALSAJ-PRIMNGNOSA-N
in ch i: InChI=1S/C19H21N5O3S/c1-2-3-4-5-8-13-21-16(20)14-18(22-13)24(19-15(26)11(25)10-27-19)17(23-14)12-7-6-9-28-12/h6-7,9,11,15,19,25-26H,2-4,10H2,1H3,(H2,20,21,22)/t11-,15-,19-/m1/s1
comment: LJ-4517 is an antagonist of the G protein-coupled A2A adenosine receptor <Reference id=44041/>.
iupac name: (2R,3R,4R)-2-[6-amino-2-(hex-1-yn-1-yl)-8-(thiophen-2-yl)-9H-purin-9-yl]oxolane-3,4-diol
synonym: compound 2 [PMID: 35977382]
synonym: LJ4517
approved: f
ligand name: LJ-4517
type: SyntheticOrganicLigand

ebaresdax
canonical SMILES: OC(=O)[C@H]1N=C(SC1(C)C)Nc1ccccc1O
isomeric SMILES: CC1([C@H](N=C(S1)Nc1ccccc1O)C(=O)O)C
in ch i key: OASISJWJIHWVKX-SECBINFHSA-N
in ch i: InChI=1S/C12H14N2O3S/c1-12(2)9(10(16)17)14-11(18-12)13-7-5-3-4-6-8(7)15/h3-6,9,15H,1-2H3,(H,13,14)(H,16,17)/t9-/m1/s1
comment: The chemical structure for ebaresdax is claimed in Cersci Therapeutics' patent WO2020159643A1 <Reference id=44037/>, which allowed us to associate this structure with their clinical lead candidate ACP-044. This was confirmed by synonym matches on PubChem. Ebaresdax (ACP-044) is a first-in-class, orally administered, non-opioid analgesic that was developed for potential to treat neuropathic, surgical and osteoarthritic pain.
iupac name: (4R)-2-(2-hydroxyanilino)-5,5-dimethyl-4H-1,3-thiazole-4-carboxylic acid
synonym: ACP-044
synonym: ACP044
synonym: compound 1 [WO2020159643A1]
approved: f
ligand name: ebaresdax
type: SyntheticOrganicLigand

olitigaltin
in ch i key: YGIDGBAHDZEYMT-MQFIMZJJSA-N
comment: Olitigaltin (GB0139) is a <Ligand id=6619/> inhibitor <Reference id=40287/> that is designed for inhalation, and is intended as a therapy for fibrotic lung conditions such as idiopathic pulmonary fibrosis (IPF) <Reference id=44035/>. In the fibrotic setting, blocking galectin-3's biological function is predicted to combat the enhanced TGF-β receptor-mediated macrophage differentiation and myofibroblast activation that drives pathological fibrotic changes <Reference id=40286/><Reference id=40287/><Reference id=40288/>.
xref: CHEMBL4297442
synonym: GB0139
synonym: GB-0139
synonym: TD-139
synonym: TD139
approved: f
ligand name: olitigaltin
type: SyntheticOrganicLigand

TL12-186
in ch i key: YNGWQHGVASHCBK-UHFFFAOYSA-N
comment: TL12-186 is a PROTAC class molecule, that targets cyclin-dependent kinase (CDK) family proteins for ubiquitination and proteasomal degradation <Reference id=44034/>. TL12-186 binds to the CDKs via the parental multi-kinase inhibitor <Ligand id=5714/> (TAE-684), and uses a <Ligand id=7348/> moiety to engage cereblon (CRBN). In engineered cell lines expressing individual CDKs, all 16 kinases were degraded by TL12-186 <Reference id=44033/>. Interestingly, cell cycle-associated CDKs 1, 2, 4, and 6 were less susceptible to TL12-186-promoted degradation than the other CDKs. Formation of the ternary complex of TL12-186 with CRBN is required for efficient CDK2 degradation.
iupac name: N-[2-[2-[2-[4-[4-[[5-chloro-4-(2-propan-2-ylsulfonylanilino)pyrimidin-2-yl]amino]phenyl]piperazin-1-yl]ethoxy]ethoxy]ethyl]-2-[[2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-4-yl]amino]acetamide
synonym: TL 12-186
approved: f
ligand name: TL12-186
type: SyntheticOrganicLigand

C004019
in ch i key: IXTMPMLKABNFTQ-LLIFGLRNSA-N
comment: C004019 is a small-molecule PROTAC that selectively promotes tau protein degradation <Reference id=44032/>. It was designed to reduce tau burden as a mechanism to improve cognitive functions in Alzheimer's disease and other tauopathies. C004019 binds simultaneously to tau and to the VHL E3-ligase to promote selective proteasomal degradation of tau.
approved: f
ligand name: C004019
type: SyntheticOrganicLigand

LSZ102
in ch i key: SJXNPGGVGZXKKI-NYYWCZLTSA-N
in ch i: InChI=1S/C25H17F3O4S/c1-25(27,28)20-12-15(26)5-9-18(20)24-23(19-10-6-16(29)13-21(19)33-24)32-17-7-2-14(3-8-17)4-11-22(30)31/h2-13,29H,1H3,(H,30,31)/b11-4+
comment: LSZ102 is a potent and orally bioavailable selective estrogen receptor degrader (SERD) <Reference id=44031/>. It was developed for as a potential treatment for ERα positive breast cancer.
synonym: LSZ-102
synonym: compound 10 [PMID: 29562737]
approved: f
ligand name: LSZ102
type: SyntheticOrganicLigand

PHTPP-1304
in ch i key: RFLBGKJLIDOOAA-RRHRGVEJSA-N
in ch i: InChI=1S/C51H50F6N4O7/c52-50(53,54)45-32-46(51(55,56)57)61-49(59-45)47(48(60-61)39-16-8-3-9-17-39)38-18-20-41(21-19-38)65-30-29-64-28-27-63-26-24-58-33-40(62)35-67-42-22-23-43(68-34-37-13-6-2-7-14-37)44(31-42)66-25-10-15-36-11-4-1-5-12-36/h1-9,11-14,16-23,31-32,40,58,62H,10,15,24-30,33-35H2/t40-/m1/s1
comment: PHTPP-1304 is a novel protein degrader <Reference id=44029/><Reference id=44030/>. It binds to the estrogen receptor β via the ERβ antagonist <Ligand id=3461/> domain, and simultaneously to the autophagy receptor p62, to target the ERβ . This class of degrader is called an AUTOphagy-TArgeting Chimera, or AUTOTAC. AUTOTACs can be designed to target proteins of interest to autophagic membranes where they undergo lysosomal degradation, in a proteasome-independent manner.
iupac name: (2R)-1-[2-[2-[2-[4-[2-phenyl-5,7-bis(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-3-yl]phenoxy]ethoxy]ethoxy]ethylamino]-3-[4-phenylmethoxy-3-(3-phenylpropoxy)phenoxy]propan-2-ol
approved: f
ligand name: PHTPP-1304
type: SyntheticOrganicLigand

WNY0824
in ch i key: QUMCIHKVKQYNPA-RUZDIDTESA-N
in ch i: InChI=1S/C31H43N9O2/c1-5-25-29-37-36-20(2)40(29)26-18-32-31(35-28(26)39(25)19-21-9-7-6-8-10-21)34-24-12-11-22(17-27(24)42-4)30(41)33-23-13-15-38(3)16-14-23/h11-12,17-18,21,23,25H,5-10,13-16,19H2,1-4H3,(H,33,41)(H,32,34,35)/t25-/m1/s1
comment: WNY0824 is a dual inhibitor of bromodomain (BET) containing kinases and polo-like kinase 1 (PLK1) <Reference id=44028/>. It was designed during the process to identify novel anticancer agents.
iupac name: 4-[[(4R)-5-(cyclohexylmethyl)-4-ethyl-1-methyl-4H-[1,2,4]triazolo[4,3-f]pteridin-7-yl]amino]-3-methoxy-N-(1-methylpiperidin-4-yl)benzamide
xref: CHEMBL4747491
synonym: PLK1/BRD4-IN-1
synonym: WNY-0824
synonym: compound 9b [PMID: 32088495]
approved: f
ligand name: WNY0824
type: SyntheticOrganicLigand

kanamycin
in ch i key: SBUJHOSQTJFQJX-NOAMYHISSA-N
in ch i: InChI=1S/C18H36N4O11/c19-2-6-10(25)12(27)13(28)18(30-6)33-16-5(21)1-4(20)15(14(16)29)32-17-11(26)8(22)9(24)7(3-23)31-17/h4-18,23-29H,1-3,19-22H2/t4-,5+,6-,7-,8+,9-,10-,11-,12+,13-,14-,15+,16-,17-,18-/m1/s1
comment: Kanamycin (also known as kanamycin A) is the main fermentation product of Streptomyces kanamyceticus <Reference id=44257/>. Additional products have been subsequently identified, including <Ligand id=12182/> (kanamycin B), kanamycin C (PubChem CID: 439582), kanamycin D (PubChem CID: 10368104) and kanamycin X (PubChem CID: 25202222). Kanamycin has activity against Gram-positive and Gram-negative bacteria and belongs to the aminoglycoside class of antibacterial compounds.
iupac name: (2R,3S,4S,5R,6R)-2-(aminomethyl)-6-[(1R,2R,3S,4R,6S)-4,6-diamino-3-[(2S,3R,4S,5S,6R)-4-amino-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2-hydroxycyclohexyl]oxyoxane-3,4,5-triol
xref: CHEMBL1384
synonym: kanamycin A
approved: t
ligand name: kanamycin
type: NaturalProductLigand

urea
canonical SMILES: NC(=O)N
isomeric SMILES: NC(=O)N
in ch i key: XSQUKJJJFZCRTK-UHFFFAOYSA-N
in ch i: InChI=1S/CH4N2O/c2-1(3)4/h(H4,2,3,4)
iupac name: urea
xref: CHEMBL985
approved: f
ligand name: urea
type: MetaboliteLigand

WWL0245
in ch i key: AORZPRLVKUMTOJ-XGDNGBMYSA-N
in ch i: InChI=1S/C45H51N11O8/c1-4-31-40-52-51-25(2)55(40)33-22-46-45(50-39(33)54(31)23-26-9-6-5-7-10-26)48-30-14-13-27(21-35(30)63-3)41(59)47-28-17-19-53(20-18-28)37(58)24-64-34-12-8-11-29-38(34)44(62)56(43(29)61)32-15-16-36(57)49-42(32)60/h8,11-14,21-22,26,28,31-32H,4-7,9-10,15-20,23-24H2,1-3H3,(H,47,59)(H,46,48,50)(H,49,57,60)/t31-,32?/m1/s1
comment: WWL0245 is a bifunctional cereblon-based PROTAC molecule that promotes ubiquitin-proteasomal degradation of BRD4 protein <Reference id=44027/>. The BET domain-binding region is based on the dual BET/PLK1 inhibitor <Ligand id=12143/>. Cereblon binding is mediated via a modified thalidomide moiety. WWL0245 exhibits selective cytotoxicity in BET inhibitor sensitive cancer cell lines such as androgen receptor (AR)-positive prostate cancer cell lines, and it promotes a more potent anti-proliferative effect than the parent BET inhibitor.
synonym: BRD4-PROTAC 12a
synonym: WWL-0245
approved: f
ligand name: WWL0245
type: SyntheticOrganicLigand

XY-06-007
in ch i key: QTDHGBJLMBQHOW-BPJPHOPQSA-N
in ch i: InChI=1S/C41H41ClN8O8/c1-22(35-37-48-47-23(2)49(37)29-15-14-26(57-3)20-28(29)36(46-35)24-10-12-25(42)13-11-24)38(53)44-19-6-4-5-18-43-33(52)21-58-31-9-7-8-27-34(31)41(56)50(40(27)55)30-16-17-32(51)45-39(30)54/h7-15,20,22,30,35H,4-6,16-19,21H2,1-3H3,(H,43,52)(H,44,53)(H,45,51,54)/t22-,30?,35+/m1/s1
comment: XY-06-007 is a cereblon (CRBN)-based PROTAC that promotes degradation of BRD4 protein <Reference id=44026/>. It was designed to bring the E3 ligase CRL4CRBN into close proximity of an engineered BRD4BD1 mutant with a L94V substitution, to provide evidence that degraders can be designed to selectively degrade a mutated protein whilst sparing the wild-type protein.
iupac name: (2R)-2-[(4S)-6-(4-chlorophenyl)-8-methoxy-1-methyl-4H-[1,2,4]triazolo[4,3-a][1,4]benzodiazepin-4-yl]-N-[5-[[2-[2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-4-yl]oxyacetyl]amino]pentyl]propanamide
approved: f
ligand name: XY-06-007
type: SyntheticOrganicLigand

HJC0152
canonical SMILES: NCCOc1ccc(cc1C(=O)Nc1ccc(cc1Cl)[N+](=O)[O-])Cl
in ch i key: DIMJVBOEXNWPOG-UHFFFAOYSA-N
comment: HJC0152 was originally identified as an orally bioavailable compound with anti-cancer properties <Reference id=44023/>, and weak anti-viral activity <Reference id=44024/>. Its chemical structure is based upon that of the signal transducer and activator of transcription 3 (STAT3)-inhibiting compound <Ligand id=8494/>. STAT3 is an oncology drug target, since excessive activation of STAT3 occurs in cancers, and is a perdictor of poor prognosis. Blocking STAT3 signalling in many cancer cell types induces growth arrest and promotes apoptosis. To mour knowledge there is no quantitative data that supports the direct interaction of HJC0152 with STAT3.
iupac name: 2-(2-aminoethoxy)-5-chloro-N-(2-chloro-4-nitrophenyl)benzamide
xref: CHEMBL2326743
synonym: compound 11 [PMID: 23459613]
synonym: HJC-0152
synonym: HJC-1-52
synonym: compound 11 [WO2014113467A1]
approved: f
ligand name: HJC0152
type: SyntheticOrganicLigand

CYD0618
in ch i key: UAOUIVVJBYDFKD-XKCDOFEDSA-N
in ch i: InChI=1S/C24H30N2O5S/c1-5-8-25-20-26-16-13(32-20)9-21(3,4)15-19(29)24(30)23-14(22(15,16)10-31-24)7-6-12(18(23)28)11(2)17(23)27/h5,12,14-15,18-19,28-30H,1-2,6-10H2,3-4H3,(H,25,26)/t12-,14-,15+,18+,19-,22-,23-,24-/m0/s1
comment: CYD0618 is a derivative of the natural product oridonin <Reference id=44021/>. Oridonin is an active compound found in the Rabdosia rubescen plant that is used in Chinese traditional medicine for its anti-inflammatory effects. CYD0618 has anti-fibrotic actions in the liver which are proposed to be mediated via inhibition of the NF-κB signalling pathway <Reference id=44021/>. This compound also has reported antiproliferative activity in cancer cell lines <Reference id=44022/>.
xref: CHEMBL3919658
synonym: compound 28 [PMID: 27344488]
synonym: CYD-0618
approved: f
ligand name: CYD0618
type: SyntheticOrganicLigand

MS8815
in ch i key: AOIZISCRIVNZJJ-XWJFFXCMSA-N
in ch i: InChI=1S/C65H87N9O8S/c1-9-73(51-25-31-82-32-26-51)55-35-50(34-53(44(55)4)61(78)67-38-54-42(2)33-43(3)69-62(54)79)48-21-19-47(20-22-48)39-71-27-29-72(30-28-71)58(77)16-14-12-10-11-13-15-57(76)70-60(65(6,7)8)64(81)74-40-52(75)36-56(74)63(80)66-37-46-17-23-49(24-18-46)59-45(5)68-41-83-59/h17-24,33-35,41,51-52,56,60,75H,9-16,25-32,36-40H2,1-8H3,(H,66,80)(H,67,78)(H,69,79)(H,70,76)/t52-,56+,60-/m1/s1
comment: MS8815 is a bifunctional PROTAC molecule that targets the enhancer of zeste homolog 2 (EZH2) protein for degradation <Reference id=44018/>. It contains a VHL-binding ligand VHL-1 (a.k.a. VH032 <Reference id=44020/>; PubChem CID 77232228; Kd 188 nM) to recruit the VHL E3 ligase, and the EZH2 engager is the FDA-approved drug <Ligand id=7011/> (EPZ-6438). EZH2 overexpression is a marker of poor prognosis in triple-negative breast cancer (TNBC). Protein degrading agents are proposed as alternatives to small molecule inhibitors, and are of particular use for 'difficult-to-drug' protein targets.
iupac name: (2S,4R)-1-((S)-2-(9-(4-((3′-(((4,6-Dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)carbamoyl)-5′-(ethyl(tetrahydro-2H-pyran-4-yl)amino)-4′-methyl-[1,1′-biphenyl]-4-yl)methyl)piperazin-1-yl)-9-oxononanamido)-3,3-dimethylbutanoyl)-4-hydroxy-N-(4-(4-methylthiazol-5-yl)benzyl)pyrrolidine-2-carboxamide
synonym: compound 16 [PMID: 35837138]
synonym: MS-8815
approved: f
ligand name: MS8815
type: SyntheticOrganicLigand

TDRL-551
in ch i key: QHNTZIUSUGGSNE-UHFFFAOYSA-N
comment: TDRL-551 is a small molecule that was desigend by NERx BioSciences to block the interaction between replication protein A (RPA) and single stranded DNA, as a mechanism to enhance the efficacy of platinum-containing chemotherapy drugs <Reference id=44017/>.
xref: CHEMBL4644460
synonym: TDRL551
synonym: compound 4 [PMID: 32550990]
approved: f
ligand name: TDRL-551
type: SyntheticOrganicLigand

(R)-AS-1
canonical SMILES: C[C@@H](N1C(=O)CCC1=O)C(=O)NCc1ccccc1
isomeric SMILES: O=C(NCc1ccccc1)[C@@H](C)N1C(=O)CCC1=O
in ch i key: XVSYJYYNUSOPAQ-SNVBAGLBSA-N
in ch i: InChI=1S/C14H16N2O3/c1-10(16-12(17)7-8-13(16)18)14(19)15-9-11-5-3-2-4-6-11/h2-6,10H,7-9H2,1H3,(H,15,19)/t10-/m1/s1
comment: (R)-AS-1 acts as a positive allosteric modulator (PAM) of the excitatory amino acid transporter, EAAT2 (SLC1A2) that enhances glutamate uptake in vitro <Reference id=44013/>. It exhibits potent antiseizure activity in mouse seizure models. (R)-AS-1 is one of the chemical structures that are claimed in patent WO2020214043A1 <Reference id=44014/>.
iupac name: (2R)-N-benzyl-2-(2,5-dioxopyrrolidin-1-yl)propanamide
synonym: (R)-7
approved: f
ligand name: (R)-AS-1
type: SyntheticOrganicLigand

FXIa inhibitor 3f
isomeric SMILES: Clc1c(c(c(cc1)n1nnc(c1)Cl)c1ccc([n+](c1)[O-])[C@@H](CCOC(F)F)n1ncc(c1)c1cnnn1C)F
in ch i key: BETDGMHNHGHORO-MRXNPFEDSA-N
comment: This compound is an orally bioavailable inhibitor of the blood coagulation protease, factor XIa (F11a) <Reference id=44010/>. F11a is a key component of the intrinsic coagulation pathway, and it is an active target for antithrombotic drug discovery. Compound 3f was designed by investigators at Janssen Research & Development.
iupac name: 5-[3-chloro-6-(4-chlorotriazol-1-yl)-2-fluorophenyl]-2-[(1R)-3-(difluoromethoxy)-1-[4-(3-methyltriazol-4-yl)pyrazol-1-yl]propyl]-1-oxidopyridin-1-ium
approved: f
ligand name: FXIa inhibitor 3f
type: SyntheticOrganicLigand

compound 33a [PMID: 35944901]
in ch i key: VGOALPIDEXVYQI-UHFFFAOYSA-N
in ch i: InChI=1S/C26H17F3N6O/c1-17-4-5-19(11-18(17)6-7-22-15-31-24-3-2-8-32-35(22)24)25(36)33-21-12-20(26(27,28)29)13-23(14-21)34-10-9-30-16-34/h2-5,8-16H,1H3,(H,33,36)
comment: This compound is an inhibitor of the ongogenic BCR-Abl kinase, that was designed to decrease cardiotoxicity compared to existing therapeutics in this class, such as <Ligand id=5890/> <Reference id=44002/>. Like ponatinib, 33a potently inhibits both wild type BCR-Abl and mutant BCR-Abl kinase that expresses the gatekeeper resistance mutation T315I. Ponatinib is currently (August 2022) the only Abl kinase inhibitor that is effective in CML with the BCR-AblT315I mutation.
iupac name: 3-(2-imidazo[1,2-b]pyridazin-3-ylethynyl)-N-[3-imidazol-1-yl-5-(trifluoromethyl)phenyl]-4-methylbenzamide
approved: f
ligand name: compound 33a [PMID: 35944901]
type: SyntheticOrganicLigand

vanillobiocin
in ch i key: LNDDBMXOCFEELJ-CPPKFOPJSA-N
comment: Vanillobiocin is an aminocoumarin antibacterial compound isolated from the culture broth of a cloQ- mutant of the clorobiocin producer Streptomyces roseochromogenes <Reference id=44003/>. The same study also identified <Ligand id=12129/> and <Ligand id=12128/>.
iupac name: [(3R,4S,5R,6S)-6-[8-chloro-4-hydroxy-3-[(4-hydroxy-3-methoxybenzoyl)amino]-2-oxochromen-7-yl]oxy-5-hydroxy-3-methoxy-2,2-dimethyloxan-4-yl] 5-methyl-1H-pyrrole-2-carboxylate
xref: CHEMBL1275884
synonym: novclobiocin 311
approved: f
ligand name: vanillobiocin
type: NaturalProductLigand

isovanillobiocin
in ch i key: AKYRQFMQZJFLAE-AUHTVUCRSA-N
comment: Isovanillobiocin is an aminocoumarin antibacterial compound isolated from the culture broth of a cloQ- mutant of the clorobiocin producer Streptomyces roseochromogenes <Reference id=44003/>. The same study also identified <Ligand id=12130/> and <Ligand id=12128/>.
iupac name: [(2S,3R,4R,5R)-2-[8-chloro-4-hydroxy-3-[(4-hydroxy-3-methoxybenzoyl)amino]-2-oxochromen-7-yl]oxy-4-hydroxy-5-methoxy-6,6-dimethyloxan-3-yl] 5-methyl-1H-pyrrole-2-carboxylate
xref: CHEMBL1275899
synonym: novclobiocin 312
approved: f
ligand name: isovanillobiocin
type: NaturalProductLigand

isepamicin
in ch i key: UDIIBEDMEYAVNG-ZKFPOVNWSA-N
in ch i: InChI=1S/C22H43N5O12/c1-22(35)6-36-20(15(33)18(22)26-2)39-17-8(27-19(34)9(28)4-23)3-7(25)16(14(17)32)38-21-13(31)12(30)11(29)10(5-24)37-21/h7-18,20-21,26,28-33,35H,3-6,23-25H2,1-2H3,(H,27,34)/t7-,8+,9-,10+,11+,12-,13+,14-,15+,16+,17-,18+,20+,21+,22-/m0/s1
comment: Isepamicin is a semisynthetic derivative of gentamicin B, with activity against Gram-negative bacteria <Reference id=44016/>. It belongs to the aminoglycoside class of antibacterial compounds.
iupac name: (2S)-3-amino-N-[(1R,2S,3S,4R,5S)-5-amino-4-[(2R,3R,4S,5S,6R)-6-(aminomethyl)-3,4,5-trihydroxyoxan-2-yl]oxy-2-[(2R,3R,4R,5R)-3,5-dihydroxy-5-methyl-4-(methylamino)oxan-2-yl]oxy-3-hydroxycyclohexyl]-2-hydroxypropanamide
xref: CHEMBL272080
synonym: HAPA-B
synonym: Sch 21420
synonym: Sch-21420
approved: t
ligand name: isepamicin
type: SyntheticOrganicLigand

dibekacin
in ch i key: JJCQSGDBDPYCEO-XVZSLQNASA-N
in ch i: InChI=1S/C18H37N5O8/c19-4-6-1-2-7(20)17(28-6)30-15-8(21)3-9(22)16(14(15)27)31-18-13(26)11(23)12(25)10(5-24)29-18/h6-18,24-27H,1-5,19-23H2/t6-,7+,8-,9+,10+,11-,12+,13+,14-,15+,16-,17+,18+/m0/s1
comment: Dibekacin is a semisynthetic derivative of <Ligand id=12182/> (kanamycin B), with activity against Gram-positive and Gram-negative bacteria <Reference id=44012/>. It belongs to the aminoglycoside class of antibacterial compounds.
iupac name: (2S,3R,4S,5S,6R)-4-amino-2-[(1S,2S,3R,4S,6R)-4,6-diamino-3-[(2R,3R,6S)-3-amino-6-(aminomethyl)oxan-2-yl]oxy-2-hydroxycyclohexyl]oxy-6-(hydroxymethyl)oxane-3,5-diol
xref: CHEMBL560976
synonym: 3',4'-dideoxykanamycin B
synonym: dideoxykanamycin B
synonym: debecacin
approved: t
ligand name: dibekacin
type: SyntheticOrganicLigand

clorobiocin
in ch i key: FJAQNRBDVKIIKK-LFLQOBSNSA-N
comment: Clorobiocin was originally isolated from the actinomycete Streptomyces roseochromogenes and belongs to the aminocoumarins.
iupac name: [(3R,4S,5R,6S)-6-[8-chloro-4-hydroxy-3-[[4-hydroxy-3-(3-methylbut-2-enyl)benzoyl]amino]-2-oxochromen-7-yl]oxy-5-hydroxy-3-methoxy-2,2-dimethyloxan-4-yl] 5-methyl-1H-pyrrole-2-carboxylate
xref: CHEMBL303984
synonym: chlorobiocin
synonym: RP 18,631
synonym: antibiotic RP 18,631
synonym: RP 18631
synonym: 18631 RP
approved: f
ligand name: clorobiocin
type: NaturalProductLigand

novclobiocin 101
in ch i key: GMMYCBAAMDJSHV-YQQRZDPSSA-N
in ch i: InChI=1S/C35H38N2O11/c1-17(2)7-9-19-15-20(10-14-24(19)38)31(41)37-26-27(39)22-12-11-21(16-25(22)46-33(26)43)45-34-28(40)29(30(44-6)35(4,5)48-34)47-32(42)23-13-8-18(3)36-23/h7-8,10-16,28-30,34,36,38-40H,9H2,1-6H3,(H,37,41)/t28-,29+,30-,34-/m1/s1
comment: Novclobiocin 101 is an aminocoumarin antibacterial compound and a structural analogue of <Ligand id=12127/> <Reference id=44008/>.
iupac name: [(3R,4S,5R,6R)-5-hydroxy-6-[4-hydroxy-3-[[4-hydroxy-3-(3-methylbut-2-enyl)benzoyl]amino]-2-oxochromen-7-yl]oxy-3-methoxy-2,2-dimethyloxan-4-yl] 5-methyl-1H-pyrrole-2-carboxylate
approved: f
ligand name: novclobiocin 101
type: NaturalProductLigand

MAGLi 432
in ch i key: BKTASVDLNMGMFP-FUHWJXTLSA-N
comment: MAGLi 432 is reported as a non-covalent, potent and selective inhibitor of monoacylglycerol lipase (MAGL; MGLL) <Reference id=43994/><Reference id=43993/>. It was designed as an anti-inflammatory modulator, that was proposed to reduce pools of arachidonic acid in the brain, leading to reduced cyclooxygenase-mediated prostaglandin production and prostaglandin-induced neuroinflammation.
iupac name: [(7R,9aR)-7-(4-chlorophenyl)-1,3,4,6,7,8,9,9a-octahydropyrido[1,2-a]pyrazin-2-yl]-(2-bromo-3-methoxyphenyl)methanone
approved: f
ligand name: MAGLi 432
type: SyntheticOrganicLigand

compound 4e [PMID: 35546685]
in ch i key: PPZSTJQLZOPKBO-LGXAAPQCSA-N
in ch i: InChI=1S/C37H49N11O2/c1-25-11-9-10-18-46(25)36-42-41-33-17-14-27(24-47(33)36)50-31-16-15-30(28-12-7-8-13-29(28)31)39-35(49)40-34-21-32(37(2,3)4)43-48(34)26-22-38-45(23-26)20-19-44(5)6/h7-8,12-14,17,21-25,30-31H,9-11,15-16,18-20H2,1-6H3,(H2,39,40,49)/t25-,30-,31+/m0/s1
comment: This compound is an inhibitor of the α and β isoforms of p38 MAPK (MAPK14 and MAPK11 respectively) <Reference id=43992/>. It was designed to be delivered by inhalation as a therapy for inflammatory lung diseases. We suspect that this is Chiesi Farmaceutici's lead CHF-6297, but name-to-structure for CHF-6297 has not been published.
iupac name: 1-[5-tert-butyl-2-[1-[2-(dimethylamino)ethyl]pyrazol-4-yl]pyrazol-3-yl]-3-[(1S,4R)-4-[[3-[(2S)-2-methylpiperidin-1-yl]-[1,2,4]triazolo[4,3-a]pyridin-6-yl]oxy]-1,2,3,4-tetrahydronaphthalen-1-yl]urea
synonym: CHF-6297
synonym: CHF6297
synonym: CHI 91040
synonym: CHI91040
synonym: p38α MAPK-IN-5
approved: f
ligand name: compound 4e [PMID: 35546685]
type: SyntheticOrganicLigand

INCB13739
in ch i key: BDQCDIWFPIDPQU-NDEPHWFRSA-N
in ch i: InChI=1S/C28H25N3O4/c1-29-24(32)23-11-8-19(16-30-23)18-6-9-20(10-7-18)27(12-13-27)26(34)31-15-14-28(17-31)22-5-3-2-4-21(22)25(33)35-28/h2-11,16H,12-15,17H2,1H3,(H,29,32)/t28-/m0/s1
comment: INCB13739 is an orally bioavailable, nonsteroidal inhibitor of 11β-hydroxysteroid dehydrogenase 1 (11-βHSD1; HSD11B1) <Reference id=43991/>. It is a clinical lead for the control of glucose levels in the treatment of type 2 diabetes mellitus.
iupac name: N-methyl-5-[4-[1-[(1R)-3-oxospiro[2-benzofuran-1,3'-pyrrolidine]-1'-carbonyl]cyclopropyl]phenyl]pyridine-2-carboxamide
synonym: Compound 39 [PMID: 35537608]
approved: f
ligand name: INCB13739
type: SyntheticOrganicLigand

RLX-33
in ch i key: LTOAWFRZXVPHAJ-UHFFFAOYSA-N
in ch i: InChI=1S/C24H19ClN4O4/c25-18-7-3-15(4-8-18)22-27-24(33-28-22)16-5-9-19(10-6-16)26-23(31)17-12-21(30)29(13-17)14-20-2-1-11-32-20/h1-11,17H,12-14H2,(H,26,31)
comment: RLX-33 is a nonpeptide antagonist of the neuropeptide receptor RXFP3 (relaxin family peptide receptor 3) <Reference id=43990/>. Targeting the RXFP3 system is being evaluated as an approach to regulate physiological processes including appetite control, and motivation for reward.
synonym: compound 33 [PMID: 35594150]
synonym: RLX33
approved: f
ligand name: RLX-33
type: SyntheticOrganicLigand

NVP-CLR457
in ch i key: IEYOHYVYEJVEJJ-SKDRFNHKSA-N
in ch i: InChI=1S/C18H20F3N7O4/c1-9-12(8-29)28(17(30)32-9)13-6-11(24-16(25-13)27-2-4-31-5-3-27)10-7-23-15(22)26-14(10)18(19,20)21/h6-7,9,12,29H,2-5,8H2,1H3,(H2,22,23,26)/t9-,12+/m1/s1
comment: NVP-CLR457 is an orally bioavailable inhibitor of Class IA phosphoinositol-3-kinases (PI3Ks) <Reference id=43989/>. Inhibitors of this type are being evaluated as an approach to cancer treatment that has predicted application over a broad range of tumour types.
iupac name: (4S,5R)-3-[6-[2-amino-4-(trifluoromethyl)pyrimidin-5-yl]-2-morpholin-4-ylpyrimidin-4-yl]-4-(hydroxymethyl)-5-methyl-1,3-oxazolidin-2-one
synonym: compound 40 [PMID: 35500094]
approved: f
ligand name: NVP-CLR457
type: SyntheticOrganicLigand

compound 20 [PMID: 35584373]
in ch i key: GTVLCHCOKLXHLY-UHFFFAOYSA-N
in ch i: InChI=1S/C22H22FN3O5S/c1-14-18(22(25-31-14)15-3-6-17(23)7-4-15)12-30-20-8-5-16-11-26(10-9-19(16)24-20)21(27)13-32(2,28)29/h3-8H,9-13H2,1-2H3
comment: This compound is reported as a negative allosteric modulator (NAM) of ligand-gated α5-GABAA receptors that is orally bioavailable <Reference id=43988/>. α5-selective inhibitors are being evaluated as a mechanism to restore normal neuronal activity and improve the cognitive deficit that's associated with schizophrenia.
iupac name: 1-[2-[[3-(4-fluorophenyl)-5-methyl-1,2-oxazol-4-yl]methoxy]-7,8-dihydro-5H-1,6-naphthyridin-6-yl]-2-methylsulfonylethanone
approved: f
ligand name: compound 20 [PMID: 35584373]
type: SyntheticOrganicLigand

pevonedistat
in ch i key: MPUQHZXIXSTTDU-QXGSTGNESA-N
in ch i: InChI=1S/C21H25N5O4S/c22-31(28,29)30-11-14-9-15(10-19(14)27)26-8-7-17-20(23-12-24-21(17)26)25-18-6-5-13-3-1-2-4-16(13)18/h1-4,7-8,12,14-15,18-19,27H,5-6,9-11H2,(H2,22,28,29)(H,23,24,25)/t14-,15+,18-,19-/m0/s1
comment: Pevonedistat (MLN4924) is an inhibitor of the NEDD8 activating enzyme (NAE) <Reference id=43986/>, which is a heterodimer of NAE1 (NAE1; Q13564) and UBA3 subunits. Pevonedistat is structurally similar to the NAE reaction product adenosine 5′-monophosphate (AMP), and interacts with nucleotide-binding site of NAE. NAE is essential for the NEDD8 conjugation pathway which controls the activity of the cullin-RING ubiquitin E3 ligases. NAE inhibitors are proposed to disrupt cullin-RING ligase-mediated protein turnover and to promote apoptosis in human tumour cells.
xref: CHEMBL1231160
synonym: MLN 4924
synonym: MLN4924
synonym: MLN-4924
synonym: TAK-924
synonym: TAK924
approved: f
ligand name: pevonedistat
type: SyntheticOrganicLigand

MRTX1719
in ch i key: BZKIOORWZAXIBA-UHFFFAOYSA-N
comment: MRTX1719 is an inhibitor of protein arginine methyltransferase 5 (PRMT5) <Reference id=43985/>. As a component of the methylosome, PRMT5's methylation activity is essential for mammalian cell survival. In certain cancers with defects in the methionine salvage pathway, inhibiting PRMT5 is lethal <Reference id=43984/>. Thus, PRMT5 is an oncology drug target.
iupac name: 2-[4-[4-(aminomethyl)-1-oxo-2H-phthalazin-6-yl]-2-methylpyrazol-3-yl]-4-chloro-6-cyclopropyloxy-3-fluorobenzonitrile
synonym: MRTX-1719
synonym: (M)-27
approved: f
ligand name: MRTX1719
type: SyntheticOrganicLigand

compound 15 [PMID: 35034442]
in ch i key: KDDSSBXRLQRJDR-GBIUOOPFSA-N
comment: Compound 15 inhibits phosphate uptake via the NaPi2b transporter (SLC34A2) of the small intestine <Reference id=43983/>. NaPi2b inhibitors are being considered for the treatment of hyperphosphatemia.
iupac name: (E)-1-(3-((3-(2-(4-Chloro-3-(trifluoromethyl)benzylidene)hydrazine-1-carbonyl)-6,6-dimethyl-4,5,6,7-tetrahydrobenzo[b]thiophen-2-yl)carbamoyl)phenyl)-20-(2-methoxyethyl)-2,5,8,11,14,17-hexaoxa-20-azadocosan-22-oic Acid
approved: f
ligand name: compound 15 [PMID: 35034442]
type: SyntheticOrganicLigand

example 2 [WO2013026797A1]
in ch i key: UHYCLWAANUGUMN-UHFFFAOYSA-N
comment: This is one of the compounds that are claimed as PDE4B inhibitors in Boehringer Ingelheim's patent WO2013026797A1 <Reference id=43980/>. The compounds are claimed for potential to treat inflammatory or allergic diseases of the respiratory tract, such as COPD or asthma. Boehringer Ingelheim's oral PED4B clinical lead BI 1015550 has entered clinical studies <Reference id=43981/><Reference id=43982/>, but as no structure has been disclosed, it is not clear if BI 1015550 is one of the examples in WO2013026797A1.
approved: f
ligand name: example 2 [WO2013026797A1]
type: SyntheticOrganicLigand

TAS1553
in ch i key: DUYRWEBTZNUILI-DIFFPNOSSA-N
comment: TAS1553 is a small-molecule inhibitor of the interaction between ribonucleotide reductase R1 and R2 subunits <Reference id=43979/>. It binds to the R1 subunit. As a rate-limiting enzyme for <Ligand id=de novo/> dNTP production, ribonucleotide reductase is a molecular target for cancer therapeutics, as its inhibition blocks DNA synthesis and inhibits proliferation of tumour cells. TAS1553 is orally bioavailable.
iupac name: 5-chloro-2-[[(1S,2R)-2-(6-fluoro-2,3-dimethylphenyl)-1-(2-oxo-3H-1,3,4-oxadiazol-5-yl)propyl]sulfamoyl]benzamide
synonym: TAS-1553
approved: f
ligand name: TAS1553
type: SyntheticOrganicLigand

NTQ1062
in ch i key: RXNPEQZHMGFNAY-GEALJGNFSA-N
in ch i: InChI=1S/C25H31ClN6O2/c1-14(2)27-12-18(16-4-6-17(26)7-5-16)25(34)32-9-8-31(19-11-20(19)32)24-22-15(3)10-21(33)30-23(22)28-13-29-24/h4-7,13-15,18-20,27H,8-12H2,1-3H3,(H,28,29,30,33)/t15-,18-,19+,20-/m1/s1
comment: NTQ1062 is a potent and oprally bioavailable inhibitor of Akt family protein kinases, that has potent antitumour efficacies in vitro and in vivo <Reference id=43978/>. It is an onclolgy clinical lead.
iupac name: (5R)-4-[(1S,6R)-5-[(2S)-2-(4-chlorophenyl)-3-(propan-2-ylamino)propanoyl]-2,5-diazabicyclo[4.1.0]heptan-2-yl]-5-methyl-6,8-dihydro-5H-pyrido[2,3-d]pyrimidin-7-one
synonym: NTQ-1062
synonym: compound 22b [PMID: 35679512]
approved: f
ligand name: NTQ1062
type: SyntheticOrganicLigand

MK-0159
in ch i key: JUVJFMVGYBBDKN-HDJSIYSDSA-N
in ch i: InChI=1S/C20H24N4O3S/c1-26-8-9-27-14-4-2-13(3-5-14)23-20(25)16-10-17(18-11-21-12-28-18)24-19-15(16)6-7-22-19/h6-7,10-14H,2-5,8-9H2,1H3,(H,22,24)(H,23,25)/t13-,14-
comment: MK-0159 is an orally bioavailable, small molecule inhibitor of CD38's enzymatic activity <Reference id=43977/>. It was developed to help determine the protective potential of CD38 inhibition in ischemia/reperfusion injury.
iupac name: N-[4-(2-methoxyethoxy)cyclohexyl]-6-(1,3-thiazol-5-yl)-1H-pyrrolo[2,3-b]pyridine-4-carboxamide
synonym: MK0159
synonym: compound 37 [PMID: 35762533]
approved: f
ligand name: MK-0159
type: SyntheticOrganicLigand

iclepertin
in ch i key: MYHDQTVHHMSLEF-DDBGAENHSA-N
comment: Iclepertin (BI 425809) is an oral glycine transporter-1 (GlyT1; SLC6A9) inhibitor <Reference id=43972/>. Inhibiting GlyT1 increases the extracellular concentration of glycine which is a NMDA receptor co-agonist. This mecahnism is predicted to combat the neural network dysfunction and cognitive impairment that's associated with schizophrenia, and potentially Alzheimer's disease.
synonym: BI 425809
synonym: BI-425809
synonym: BI425809
approved: f
ligand name: iclepertin
type: SyntheticOrganicLigand

BMS-986339
in ch i key: AEMZJBZKICOPPC-RNMMDBENSA-N
in ch i: InChI=1S/C35H41F4N3O4/c1-30(2,36)29-40-28(41-46-29)33-15-12-32(13-16-33,14-17-33)21-42(27(43)24-19-34(45,20-24)35(37,38)39)26-7-5-6-23(18-26)22-8-10-25(11-9-22)31(3,4)44/h5-11,18,24,44-45H,12-17,19-21H2,1-4H3/t24-,32?,33?,34+
comment: BMS-986339 is an oral, nonbile acid farnesoid X receptor (FXR) agonist that was developed for potential to treat nonalcoholic steatohepatitis via induction of FGF15 in the liver and ileum <Reference id=43971/>.
iupac name: N-[[4-[5-(2-fluoropropan-2-yl)-1,2,4-oxadiazol-3-yl]-1-bicyclo[2.2.2]octanyl]methyl]-3-hydroxy-N-[3-[4-(2-hydroxypropan-2-yl)phenyl]phenyl]-3-(trifluoromethyl)cyclobutane-1-carboxamide
synonym: compound 32 [PMID: 35704802]
synonym: BMS986339
approved: f
ligand name: BMS-986339
type: SyntheticOrganicLigand

bexotegrast
in ch i key: CWOFQJBATWQSHL-DEOSSOPVSA-N
in ch i: InChI=1S/C27H36N6O3/c1-36-18-17-33(15-5-4-8-21-12-11-20-7-6-14-28-25(20)31-21)16-13-24(27(34)35)32-26-22-9-2-3-10-23(22)29-19-30-26/h2-3,9-12,19,24H,4-8,13-18H2,1H3,(H,28,31)(H,34,35)(H,29,30,32)/t24-/m0/s1
comment: Bexotegrast (PLN-74809; Pliant Therapeutics) is a dual-selective integrin inhibitor/antagonist that was developed for anti-fibrosis potential <Reference id=43968/>. The αv integrins regulate TGFβ activation (catalysing conversion of latent TGFβ isoforms to the active forms) and fibrogenesis in pulmonary fibrosis models <Reference id=43970/><Reference id=43969/>, and αvβ6 and αvβ1 integrins are expressed on abnormal epithelial cells and fibroblasts (respectively) in human fibrotic lung tissue. By antagonising the function of both of these, bexotegrast restricts TGFβ activation and downstream signalling, which has been shown to promote an anti-fibrogenic effect in lung tissue samples from patients with idiopathic pulmonary fibrosis (IPF) <Reference id=43968/>.
iupac name: (2S)-4-[2-methoxyethyl-[4-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)butyl]amino]-2-(quinazolin-4-ylamino)butanoic acid
synonym: PLN-74809
synonym: PLN74809
approved: f
ligand name: bexotegrast
type: SyntheticOrganicLigand

LL-K9-3
in ch i key: NPRIWHDFWDSJRZ-YFNKSVMNSA-N
in ch i: InChI=1S/C31H49N5O6S3/c1-20(2)23-8-7-21(3)15-24(23)41-18-26(37)32-11-14-45(39,40)36-12-9-22(10-13-36)29(38)35-30-34-17-28(44-30)43-19-27-33-16-25(42-27)31(4,5)6/h16-17,20-24H,7-15,18-19H2,1-6H3,(H,32,37)(H,34,35,38)/t21-,23+,24-/m1/s1
comment: LL-K9-3 is a small-molecule that induces simultaneous degradation of CDK9 and cyclin T1 (CDK9-Cyclin T1 heterodimers) that was developed for anti-tumour potential in transcriptionally addicted cancers <Reference id=43967/>. It uses hydrophobic tagging technology (HyT) to induce polyubiquitination of CDK9-cyclin T1 complexes, as a mechanism to promote proteasome-mediated degradation of both proteins. In particular LL-K9-3 was evaluated for its inhibitory effects on CDK9 and androgen receptor-mediated signalling pathways in prostate cancer. LL-K9-3 elicits more potent anti-proliferative and pro-apoptotic effects than its parental CDK9 inhibitor <Ligand id=5670/> (a.k.a. SNS032), or than the CDK9-only PROTAC <Ligand id=10547/>.
iupac name: N-(5-(((5-(tert-Butyl)oxazol-2-yl)methyl)thio)thiazol-2-yl)-1-((2-(2-(((1R, 2S, 5R)-2-isopropyl-5-methylcyclohexyl)oxy) acetamido)ethyl)sulfonyl)piperidine-4-carboxamide
approved: f
ligand name: LL-K9-3
type: SyntheticOrganicLigand

farudodstat
in ch i key: OMPATGZMNFWVOH-UHFFFAOYSA-N
in ch i: InChI=1S/C19H14F2N2O3/c1-26-13-5-2-4-11(8-13)12-9-15(20)17(16(21)10-12)23-18-14(19(24)25)6-3-7-22-18/h2-10H,1H3,(H,22,23)(H,24,25)
comment: Farudodstat (ASLAN003; ASLAN Pharmaceuticals) is an orally bioactive inhibitor of dihydroorotate dehydrogenase (DHODH) <Reference id=43966/>. It was developed for antineoplastic activity in acute myeloid leukemia.
iupac name: 2-[2,6-difluoro-4-(3-methoxyphenyl)anilino]pyridine-3-carboxylic acid
xref: CHEMBL2263632
synonym: LAS186323
synonym: ASLAN003
synonym: ASLAN-003
approved: f
ligand name: farudodstat
type: SyntheticOrganicLigand

compound 19 [PMID: 35925768]
in ch i key: XEDJGCIOZDHXOR-JTQLQIEISA-N
comment: Compound 19 is one of the two dihydroorotate dehydrogenase (DHODH) inhibitor lead candidates discovered by Cisar et al. (2022; Janssen Research & Development) <Reference id=43964/>. Compounds 19 and 29 were selected based on their combination of DHODH inhibition potency in biochemical and cellular assays, oral bioactivity, drug-like physicochemical properties, and efficacy in an AML xenograft model. Janssen have clinical candidate DHODH inhibitor JNJ-74856665 <Reference id=43965/> in Phase 1 for AML (NCT04609826), but its structure has not been disclosed (as of August 2022).
iupac name: N-(2-chloro-4-methylpyridin-3-yl)-6-[4-ethyl-3-(hydroxymethyl)-5-oxo-1,2,4-triazol-1-yl]-5-fluoro-2-[(2S)-1,1,1-trifluoropropan-2-yl]oxypyridine-3-carboxamide
approved: f
ligand name: compound 19 [PMID: 35925768]
type: SyntheticOrganicLigand

plazinemdor
in ch i key: NULHGWQIRTXKAY-UHFFFAOYSA-N
comment: Plazinemdor (CAD-9303) is a positive allosteric modulator (PAM) of N-Methyl-D-aspartate (NMDA) ligand-gated ion channel receptors that was designed as a potential treatment for the negative and cognitive symptoms that are experienced by patients with schizophrenia. Its chemical structure and use are claimed in Cadent Therapeutics' patent WO2020086136A2 <Reference id=43847/>.
iupac name: 5-(3-chloro-4-fluorophenyl)-7-cyclopropyl-3-[2-(3-fluoro-3-methylazetidin-1-yl)-2-oxoethyl]pyrrolo[2,3-d]pyrimidin-4-one
synonym: CAD-9303
synonym: CAD9303
synonym: Compound 1 [WO2020086136A2]
approved: f
ligand name: plazinemdor
type: SyntheticOrganicLigand

compound 1k [PMID: 35912476]
in ch i key: DGJMHKMYSDYOFP-MRXNPFEDSA-N
in ch i: InChI=1S/C23H23F2N9O/c1-2-18(35)32-10-6-9-16(11-32)34-22-19(21(26)27-14-28-22)20(30-34)17-12-33(31-29-17)13-23(24,25)15-7-4-3-5-8-15/h2-5,7-8,12,14,16H,1,6,9-11,13H2,(H2,26,27,28)/t16-/m1/s1
comment: This compound is a mitogen-activated protein kinase kinase 7 (MKK7; MAP2K7) inhibitor <Reference id=43961/>. MKK7 exclusively phosphorylates downstream JNK, and represents an attractive molecular target for selectively modifying JNK signalling in human disease. 1K is suitable for in vitro work but its physicochemical properties would need to be optimised further for in vivo applications.
iupac name: (R)-1-(3-(4-Amino-3-(1-(2,2-difluoro-2-phenylethyl)-1H-1,2,3-triazol-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)piperidin-1-yl)prop-2-en-1-one
approved: f
ligand name: compound 1k [PMID: 35912476]
type: SyntheticOrganicLigand

vimnerixin
in ch i key: UCCNQCNIPRKLRP-CJNGLKHVSA-N
comment: Vimnerixin (AZD4721/RIST4721 ) is an orally bioavailable CXC chemokine receptor type 2 antagonist <Reference id=43956/>. It has minimal activity on CXCR1, so has little effect on neutrophil activation.
iupac name: N-[6-[(2R,3S)-3,4-dihydroxybutan-2-yl]oxy-2-[(4-fluorophenyl)methylsulfanyl]pyrimidin-4-yl]-3-methylazetidine-1-sulfonamide
synonym: AZD4721
synonym: AZD-4721
synonym: RIST4721
synonym: compound 4 [WO2019055509A1]
approved: f
ligand name: vimnerixin
type: SyntheticOrganicLigand

tunodafil
in ch i key: RXMDFMQMRASWOG-UHFFFAOYSA-N
in ch i: InChI=1S/C24H33N5O4S/c1-5-10-28-16-17(4)21-23(28)25-22(26-24(21)30)19-15-18(8-9-20(19)33-7-3)34(31,32)29-13-11-27(6-2)12-14-29/h8-9,15-16H,5-7,10-14H2,1-4H3,(H,25,26,30)
comment: Tunodafil (chemical structure extracted from WHO proposed INN list 127) is a phosphodiesterase 5 (PDE5) inhibitor. It is an analogue of <Ligand id=4743/>, but is a more potent PDE5 inhibitor than its predecessor. Tunodafil was developed for the treatment of erectile dysfunction, and has been examined for potential to protect against ischemic brain injury <Reference id=43955/>.
iupac name: 2-[2-ethoxy-5-(4-ethylpiperazin-1-yl)sulfonylphenyl]-5-methyl-7-propyl-3H-pyrrolo[2,3-d]pyrimidin-4-one
synonym: yonkenafil (pseudo INN)
approved: f
ligand name: tunodafil
type: SyntheticOrganicLigand

icanbelimod
in ch i key: YBIFMTGYWXNIRZ-UHFFFAOYSA-N
in ch i: InChI=1S/C23H24FN3O3/c1-14(2)9-15-3-5-16(6-4-15)22-25-21(26-30-22)17-7-8-18(20(24)10-17)11-27-12-19(13-27)23(28)29/h3-8,10,14,19H,9,11-13H2,1-2H3,(H,28,29)
comment: Icanbelimod (chemical structure extracted from WHO proposed INN list 127) is a S1P receptor agonist that has immunomodulatory action. The structure can be found in patent WO2015039587A1 (Suzhou Kangnaide Biopharmaceutical) <Reference id=43954/>. Icanbelimod is selective for S1P1 receptor compared to S1P3 receptor,
iupac name: 1-[[2-fluoro-4-[5-[4-(2-methylpropyl)phenyl]-1,2,4-oxadiazol-3-yl]phenyl]methyl]azetidine-3-carboxylic acid
xref: CHEMBL4097139
synonym: YUN88562
synonym: S1p-receptor-agonist-1
synonym: compound 2 [WO2015039587A1]
approved: f
ligand name: icanbelimod
type: SyntheticOrganicLigand

acloproxalap
canonical SMILES: Nc1cc2ccccc2nc1C(O)(C)C
isomeric SMILES: Nc1c(nc2ccccc2c1)C(C)(C)O
in ch i key: NOFRQDXKZDAYGB-UHFFFAOYSA-N
in ch i: InChI=1S/C12H14N2O/c1-12(2,15)11-9(13)7-8-5-3-4-6-10(8)14-11/h3-7,15H,13H2,1-2H3
comment: We obtained the chemical structure for acloproxalap from the WHO's proposed INN list 127 (21 July 2022). In this document it was described as an anti-inflammatory. Acloproxalap is an analogue of <Ligand id=10613/>. Like its predecessor, acloproxalap was designed as a molecular trap for pro-inflammatory Reactive Aldehyde Species (RASP) molecules that are produced by metabolic and inflammatory processes, to treat diseases in which aldehyde toxicity is implicated in the pathogenesis <Reference id=43953/>. We predict that acloproxalap is the INN for the clinical lead known as ADX-629.
iupac name: 2-(3-aminoquinolin-2-yl)propan-2-ol
synonym: Compound 5 [WO2020223685A1]
approved: f
ligand name: acloproxalap
type: SyntheticOrganicLigand

tinlorafenib
in ch i key: VVLVISDSGRHLMB-UHFFFAOYSA-N
comment: We obtained the chemical structure for tinlorafenib from the WHO's proposed INN list 127 (21 July 2022). In this document it was described as an antineoplastic. The INN indicates that it is a RAF kinase inhibitor. Further investigations revealed that tinlorafenib has the synonyms PF-07284890 and ARRY-461, that it inhibits BRAF and CRAF, and that it is orally bioavailable and able to cross the blood-brain barrier <Reference id=43952/>.
synonym: ARRY-461
synonym: ARRY461
synonym: PF-07284890
synonym: PF07284890
approved: f
ligand name: tinlorafenib
type: SyntheticOrganicLigand

exarafenib
in ch i key: GZMYLSJUNSCMTD-MOPGFXCFSA-N
in ch i: InChI=1S/C26H34F3N5O3/c1-17-3-4-21(31-25(36)34-6-5-19(15-34)14-26(27,28)29)13-22(17)20-11-23(30-18(2)16-35)32-24(12-20)33-7-9-37-10-8-33/h3-4,11-13,18-19,35H,5-10,14-16H2,1-2H3,(H,30,32)(H,31,36)/t18-,19+/m1/s1
comment: We obtained the chemical structure for exarafenib from the WHO's proposed INN list 127 (21 July 2022). In this document it was described as an antineoplastic. The structure is claimed in Kinnate Biopharma's patent WO2021081375A1 <Reference id=43951/>. This patent claims the compound as a RAF kinase inhibitor, for potential to treat cancers that are driven by RAF oncogenes. Kinnate Biopharma's pipeline includes their phase 1 pan-RAF inhibitor KIN-2787.
iupac name: (3S)-N-[3-[2-[[(2R)-1-hydroxypropan-2-yl]amino]-6-morpholin-4-ylpyridin-4-yl]-4-methylphenyl]-3-(2,2,2-trifluoroethyl)pyrrolidine-1-carboxamide
synonym: example 14 [WO2021081375A1]
approved: f
ligand name: exarafenib
type: SyntheticOrganicLigand

tilpisertib
in ch i key: VFGSKBLZRDRHOI-ZAGPDIDGSA-N
in ch i: InChI=1S/C33H33ClN8O/c1-32(2,3)18-37-28-20(15-35)16-36-29-25(28)10-21(11-26(29)34)38-30(27-17-42(40-39-27)33-12-19(13-33)14-33)23-6-5-7-24-22(23)8-9-41(4)31(24)43/h5-11,16-17,19,30,38H,12-14,18H2,1-4H3,(H,36,37)/t19?,30-,33?/m0/s1
comment: Tilpisertib (GS-4875) is an inhibitor of the serine/ threonine kinase Cot (a.k.a. MAP3K8/TPL2). It was developed by Gilead Sciences as a potential anti-inflammatory drug to treat auto-inflammatory diseases. The chemical structure is amongst those that are claimed as Cot (a.k.a. MAP3K8/TPL2) modulators in patent WO2020252151A1 <Reference id=43949/>. Inhibition of Cot (which is an upstream regulator in the MEK-ERK pathway) is expected to reduce production and signalling of TNFα. Gilead's development pipeline now contains a TPL2 inhibitor, GS-5290, that is in phase 1 for inflammatory bowel disease. GS-5290 may be follow-up lead compound <Ligand id=12081/>.
iupac name: 6-[[(S)-[1-(1-bicyclo[1.1.1]pentanyl)triazol-4-yl]-(2-methyl-1-oxoisoquinolin-5-yl)methyl]amino]-8-chloro-4-(2,2-dimethylpropylamino)quinoline-3-carbonitrile
xref: CHEMBL4802154
synonym: GS 4875
synonym: GS-4875
approved: f
ligand name: tilpisertib
type: SyntheticOrganicLigand

zanzalintinib
in ch i key: JSPCKALGNNVYOO-UHFFFAOYSA-N
in ch i: InChI=1S/C29H25FN4O5/c1-31-26(35)22-15-21-23(16-25(22)38-2)32-14-11-24(21)39-20-9-7-19(8-10-20)34-28(37)29(12-13-29)27(36)33-18-5-3-17(30)4-6-18/h3-11,14-16H,12-13H2,1-2H3,(H,31,35)(H,33,36)(H,34,37)
comment: We obtained the chemical structure for zanzalintinib from the WHO's proposed INN list 127 (21 July 2022). In this document it was described as a tyrosine kinase inhibitor and antineoplastic. The synonym list in PubChem's record for this compound suggests that zanzalintinib is the INN for Exelixis's clinical lead XL092 which is an analogue of <Ligand id=5887/> <Reference id=43946/>. XL092 is an ATP-competitive inhibitor of multiple RTKs including MET, VEGFR2, AXL and MER <Reference id=43947/>.
iupac name: 1-N'-(4-fluorophenyl)-1-N-[4-[7-methoxy-6-(methylcarbamoyl)quinolin-4-yl]oxyphenyl]cyclopropane-1,1-dicarboxamide
synonym: XL-092
synonym: XL092
synonym: CL-092
synonym: compound 8 [WO2019148044A1]
approved: f
ligand name: zanzalintinib
type: SyntheticOrganicLigand

unecritinib
in ch i key: HBWSXXBJOQKNBL-CYBMUJFWSA-N
comment: We obtained the chemical structure for unecritinib from the WHO's proposed INN list 127 (21 July 2022). In this document it was described as a tyrosine kinase inhibitor and antineoplastic. It is one of the inventions claimed in patent WO2013041038A1 (Teligene Ltd.) <Reference id=43945/>. Unecritinib was tested for anaplastic lymphoma kinase (ALK) inhibitory activity, as well as antiproliferative activity in biological assays.
iupac name: N-[3-[(1R)-1-(2,6-dichloro-3-fluorophenyl)ethoxy]-5-(1-piperidin-4-ylpyrazol-4-yl)pyridin-2-yl]acetamide
synonym: compound 18 [WO2013041038A1]
approved: f
ligand name: unecritinib
type: SyntheticOrganicLigand

tamnorzatinib
in ch i key: WHMMKPWGWNYYFE-UHFFFAOYSA-N
in ch i: InChI=1S/C32H26N4O6/c1-40-28-16-21-24(17-29(28)41-2)33-14-13-27(21)42-20-11-12-30(34-18-20)35-31(38)23-15-22-25(9-6-10-26(22)37)36(32(23)39)19-7-4-3-5-8-19/h3-5,7-8,11-18H,6,9-10H2,1-2H3,(H,34,35,38)
comment: We obtained the chemical structure for tamnorzatinib from the WHO's proposed INN list 127 (21 July 2022). In this document it was described as a tyrosine kinase inhibitor and antineoplastic. PubChem provided the synonym ONO-7475. ONO-7475 is a clinical stage inhibitor of the TAM family receptor tyrosine kinases AXL and MER, that has been developed as a drug for the treatment of leukaemia and advanced solid tumours <Reference id=43942/><Reference id=43943/>.
iupac name: N-[5-(6,7-dimethoxyquinolin-4-yl)oxypyridin-2-yl]-2,5-dioxo-1-phenyl-7,8-dihydro-6H-quinoline-3-carboxamide
synonym: ONO-7475
synonym: ONO7475
approved: f
ligand name: tamnorzatinib
type: SyntheticOrganicLigand

sacibertinib
in ch i key: ZGYIXVSQHOKQRZ-COIATFDQSA-N
in ch i: InChI=1S/C32H31ClN6O4/c1-39(2)12-5-7-31(40)38-28-15-25-27(16-30(28)43-24-10-13-41-20-24)36-18-21(17-34)32(25)37-22-8-9-29(26(33)14-22)42-19-23-6-3-4-11-35-23/h3-9,11,14-16,18,24H,10,12-13,19-20H2,1-2H3,(H,36,37)(H,38,40)/b7-5+/t24-/m0/s1
comment: We obtained the chemical structure for sacibertinib from the WHO's proposed INN list 127 (21 July 2022). In this document it was described as a tyrosine kinase inhibitor and antineoplastic. This same chemical structure is claimed in patent WO2011153942A1 <Reference id=43941/>. Inventions of this patent are described as inhibitors of erbB family receptor tyrosine kinases, in particular of EGFR and Her2 (ERBB2).
iupac name: (E)-N-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]-3-cyano-7-[(3S)-oxolan-3-yl]oxyquinolin-6-yl]-4-(dimethylamino)but-2-enamide
synonym: Example 161 [WO2011153942A1]
approved: f
ligand name: sacibertinib
type: SyntheticOrganicLigand

ruserontinib
in ch i key: WSOHOUHPUOAXIN-UHFFFAOYSA-N
in ch i: InChI=1S/C24H29N9/c1-17(2)33-22-21(29-24(33)28-19-5-4-10-25-15-19)16-26-23(30-22)27-18-6-8-20(9-7-18)32-13-11-31(3)12-14-32/h4-10,15-17H,11-14H2,1-3H3,(H,28,29)(H,26,27,30)
comment: We obtained the chemical structure for ruserontinib from the WHO's proposed INN list 127 (21 July 2022). In this document it was described as a tyrosine kinase inhibitor and antineoplastic. Ruserontinib appears to be CSPC ZhongQi Pharmaceutical's oral multikinase inhibitor SKLB1028, which inhibits of EGFR, FLT3 and Abl <Reference id=43940/>, and is active against FLT3-driven malignancies and those with mutated Abl kinase proteins.
iupac name: 2-N-[4-(4-methylpiperazin-1-yl)phenyl]-9-propan-2-yl-8-N-pyridin-3-ylpurine-2,8-diamine
xref: CHEMBL3678958
synonym: SKLB-1028
synonym: SKLB1028
approved: f
ligand name: ruserontinib
type: SyntheticOrganicLigand

dalmelitinib
in ch i key: MFEXYTURXUZOID-UHFFFAOYSA-N
in ch i: InChI=1S/C22H16FN7O2S/c1-28-9-13(7-25-28)12-5-16(23)21-26-27-22(30(21)10-12)33-14-3-4-17-15(6-14)20-18(8-24-17)29(2)19(31)11-32-20/h3-10H,11H2,1-2H3
comment: We obtained the chemical structure for dalmelitinib from the WHO's proposed INN list 127 (21 July 2022). In this document it was described as a tyrosine kinase inhibitor and antineoplastic. It has been reported as an ATP-competitive, cMET kinase inhibitor <Reference id=43939/>; cMET being the receptor for hepatocyte growth factor (HGF).
iupac name: 9-[[8-fluoro-6-(1-methylpyrazol-4-yl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl]sulfanyl]-4-methyl-[1,4]oxazino[3,2-c]quinolin-3-one
synonym: compound 4d [PMID: 27288183]
approved: f
ligand name: dalmelitinib
type: SyntheticOrganicLigand

vulolisib
in ch i key: KEEKMOIRJUWKNK-CABZTGNLSA-N
comment: We obtained the chemical structure for the INN 'vulolisib' from the WHO's proposed INN list 127 which was released on 21 July 2022. In the WHO document it is described as a phosphatidylinositol 3-kinase (PI3K) inhibitor and antineoplastic agent. This compound is claimed in patent WO2021104146A1, in which it is described as a PI3Kα-selective inhibitor, with antiproliferative activity against cancer cells that express mutated forms of PI3Kα <Reference id=43950/>.
iupac name: (2S)-2-[[2-[(4R)-4-(difluoromethyl)-2-oxo-1,3-thiazolidin-3-yl]-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepin-9-yl]amino]propanamide
synonym: Example 22 [WO2021104146A1]
approved: f
ligand name: vulolisib
type: SyntheticOrganicLigand

anizatrectinib
in ch i key: BGKSBHPSVMJTFL-IZZNHLLZSA-N
in ch i: InChI=1S/C29H32FN7O2/c1-19-27(22-15-31-20(2)32-16-22)35-37(24-10-5-4-6-11-24)28(19)34-29(38)33-26-18-36(12-13-39-3)17-25(26)21-8-7-9-23(30)14-21/h4-11,14-16,25-26H,12-13,17-18H2,1-3H3,(H2,33,34,38)/t25-,26+/m0/s1
comment: We obtained the chemical structure for anizatrectinib from the WHO's proposed INN list 127 (21 July 2022). In this document it was described as a tyrosine kinase inhibitor and antineoplastic. It is a potent and orally active inhibitor of TrkA kinase, and its structuire and use are claimed in patent WO2015175788A1 <Reference id=43938/>.
synonym: hTrkA-IN-1
synonym: BLN64892
approved: f
ligand name: anizatrectinib
type: SyntheticOrganicLigand

ansornitinib
canonical SMILES: COC(=O)c1ccc2c(n1)NC(=O)/C/2=C(/c1ccccc1)/Nc1ccc(cc1)N(C(=O)CN1CCN(CC1)C)C
isomeric SMILES: CN(C(=O)CN1CCN(CC1)C)c1ccc(N/C(=C/2/C(=O)Nc3nc(ccc23)C(=O)OC)/c2ccccc2)cc1
in ch i key: OABALTWKAJWHEA-RQZHXJHFSA-N
in ch i: InChI=1S/C30H32N6O4/c1-34-15-17-36(18-16-34)19-25(37)35(2)22-11-9-21(10-12-22)31-27(20-7-5-4-6-8-20)26-23-13-14-24(30(39)40-3)32-28(23)33-29(26)38/h4-14,31H,15-19H2,1-3H3,(H,32,33,38)/b27-26-
comment: We obtained the chemical structure for ansornitinib from the WHO's proposed INN list 127 (21 July 2022). In this document it was described as a tyrosine kinase kinase inhibitor. Ansornitinib may be ANG-3070, an oral tyrosine kinase inhibitor that was developed by Angion Biomedica for anti-fibrotic potential in kidney diseases, such as focal segmental glomerulosclerosis and immunoglobulin A nephropathy. Clinical trial of ANG-3070 was terminated in June 2022, following an unexpected and dangerous decline in kidney function in a patient who received the drug treatment. Development for idiopathic pulmonary fibrosis appears to be continuing.
iupac name: methyl 2-hydroxy-3-[N-[4-[methyl-[2-(4-methylpiperazin-1-yl)acetyl]amino]phenyl]-C-phenylcarbonimidoyl]-1H-pyrrolo[2,3-b]pyridine-6-carboxylate
synonym: ANG-3070
synonym: ANG3070
synonym: Example 1 [WO2013112959A1]
approved: f
ligand name: ansornitinib
type: SyntheticOrganicLigand

plogosertib
in ch i key: UFNLNMWVOMFWGS-SOAUALDESA-N
in ch i: InChI=1S/C34H48N8O3/c1-39-16-18-41(19-17-39)25-11-9-24(10-12-25)36-31(43)23-8-13-27(29(20-23)45-3)37-33-35-21-28-30(38-33)42(26-6-4-5-7-26)22-34(14-15-34)32(44)40(28)2/h8,13,20-21,24-26H,4-7,9-12,14-19,22H2,1-3H3,(H,36,43)(H,35,37,38)/t24-,25-
comment: We obtained the chemical structure for plogosertib from the WHO's proposed INN list 127 (21 July 2022). In this document it was described as a serine/threonine kinase inhibitor and antineoplastic. This Chemical structure mapped to PubChem CID 42640739, and compound 384 as claimed in patent WO2009040556A1 (Cyclacel Limited) which claims pyrimidine derivatives as inhibitors of kinases, 'particularly polo-like kinases' <Reference id=43936/>. Plogosertib could be CYC140, Cyclacel's PLK1 clinical lead candidate. Cancer cells with mutated KRAS or p53(-) cells are sensitive to PLK1 inhibition. In these cells it induces prolonged mitotic arrest and apoptosis.
iupac name: 4-[(9-cyclopentyl-5-methyl-6-oxospiro[8H-pyrimido[4,5-b][1,4]diazepine-7,1'-cyclopropane]-2-yl)amino]-3-methoxy-N-[4-(4-methylpiperazin-1-yl)cyclohexyl]benzamide
synonym: compound 384 [WO2009040556A1]
approved: f
ligand name: plogosertib
type: SyntheticOrganicLigand

pifusertib
in ch i key: AIFGVDXMHWGOGJ-DIVCQZSQSA-N
in ch i: InChI=1S/C26H24N4O2/c1-25(31)14-26(27,15-25)19-9-7-17(8-10-19)22-23(18-5-3-2-4-6-18)30-16-32-21-11-12-28-13-20(21)24(30)29-22/h2-13,31H,14-16,27H2,1H3/t25-,26-
comment: We obtained the chemical structure for pifusertib from the WHO's proposed INN list 127 (21 July 2022). In this document it was described as a serine/ threonine kinase inhibitor and antineoplastic. This appears to match the structure for TAS-117 which is an allosteric pan-Akt Inhibitor whose structure was depicted in <Reference id=43934/>, but the absolute stereo specification has been difficult to resolve. TAS-117 inhibits Akt1, 2, and 3 with similar potencies.
synonym: TAS-117
synonym: TAS117
approved: f
ligand name: pifusertib
type: SyntheticOrganicLigand

ocifisertib
in ch i key: DADASRPKWOGKCU-FVTQAUBDSA-N
in ch i: InChI=1S/C33H34N4O3/c1-20-17-37(18-21(2)40-20)19-23-6-4-22(5-7-23)8-12-29-26-11-9-24(14-31(26)36-35-29)28-16-33(28)27-15-25(39-3)10-13-30(27)34-32(33)38/h4-15,20-21,28H,16-19H2,1-3H3,(H,34,38)(H,35,36)/b12-8+/t20-,21+,28-,33-/m0/s1
comment: We obtained the chemical structure for ocifisertib from the WHO's proposed INN list 127 (21 July 2022). In this document it was described as a serine/ threonine kinase inhibitor and antineoplastic. The SMILES converted from the IUPAC in the INN list maps to PubChem CID 58486178, which has the Polo-Like Kinase 4 (PLK4) inhibitor CFI-400945 as one of its synonyms. CFI-400945 is first-in-class oral, and selective inhibitor of polo-like kinase 4 (PLK4) <Reference id=26632/><Reference id=26644/>. It has advanced to clinical evaluation in selected cancer patients.
iupac name: (2'S,3R)-2'-[3-[(E)-2-[4-[[(2R,6S)-2,6-dimethylmorpholin-4-yl]methyl]phenyl]ethenyl]-1H-indazol-6-yl]-5-methoxyspiro[1H-indole-3,1'-cyclopropane]-2-one
synonym: CFI-400945
synonym: CFI400945
approved: f
ligand name: ocifisertib
type: SyntheticOrganicLigand

MT-8
canonical SMILES: COc1ccc(cc1O)c1coc2c(c1=O)c(O)cc(c2)O
isomeric SMILES: COc1c(O)cc(cc1)c1coc2c(c(O)cc(O)c2)c1=O
in ch i key: FPIOBTBNRZPWJW-UHFFFAOYSA-N
in ch i: InChI=1S/C16H12O6/c1-21-13-3-2-8(4-11(13)18)10-7-22-14-6-9(17)5-12(19)15(14)16(10)20/h2-7,17-19H,1H3
comment: MT-8 (pratensein) is a plant-derived isoflavone compound that can be isolated from Kaempferia parviflora (Thai ginseng). It has been demonstrated to act as an inhibitor of TPC2 channels <Reference id=43304/>. Blocking TPC2 in vitro increases melanin production in melanosomes, and inhibits proliferation, migration and invasion of melanoma cells.
iupac name: 5,7-dihydroxy-3-(3-hydroxy-4-methoxyphenyl)chromen-4-one
xref: CHEMBL252904
synonym: pratensein
synonym: MT8
synonym: 3'-hydroxybiochanin A
approved: f
ligand name: MT-8
type: SyntheticOrganicLigand

tuvusertib
in ch i key: RBQPCTBFIPVIJN-UHFFFAOYSA-N
in ch i: InChI=1S/C16H12F2N8O/c1-25-7-21-5-11(25)12-9(18)3-20-4-10(12)23-16(27)13-14(19)24-26-6-8(17)2-22-15(13)26/h2-7H,1H3,(H2,19,24)(H,23,27)
comment: We obtained the chemical structure for tuvusertib from the WHO's proposed INN list 127 (21 July 2022). In this document it was described as a serine/ threonine kinase inhibitor and antineoplastic. The structure maps to PubChem CID 90199447, and it is one of the structures that are claimed as ATM and Rad3 related (ATR) kinase inhibitors in patent WO2014089379A1 (Vertex Pharmaceuticals) <Reference id=43933/>. We already had Vertex's lead candidate ATR inhibitors <Ligand id=11647/> (VX-803) and <Ligand id=8003/> (VE-822) in our dataset.
synonym: compound I-C-79 [WO2014089379A1]
approved: f
ligand name: tuvusertib
type: SyntheticOrganicLigand

tilpisertib fosmecarbil
in ch i key: FPQIBCPWXJSFOQ-ILNPBIMBSA-N
comment: We obtained the chemical structure for tilpisertib fosmecarbil from the WHO's proposed INN list 127 (21 July 2022). In this document it was described as a serine/ threonine kinase inhibitor and anti-inflammatory agent. The chemical structure is amongst those that are claimed as Cot (a.k.a. MAP3K8/TPL2) modulators in patent WO2020252151A1 <Reference id=43949/>. Inhibition of Cot (which is an upstream regulator in the MEK-ERK pathway) is expected to reduce production and signalling of TNFα, for application in auto-inflammatory diseases. Gilead's development pipeline contains a TPL2 inhibitor, GS-5290, that is in phase 1 for inflammatory bowel disease. Tilpisertib fosmecarbil is likely a follow-up to the parent molecule tilpisertib (formerly GS-4875) that was tested in ulcerative colitis trial NCT04130919.
iupac name: phosphonooxymethyl N-[(S)-[1-(1-bicyclo[1.1.1]pentanyl)triazol-4-yl]-(2-methyl-1-oxoisoquinolin-5-yl)methyl]-N-[8-chloro-3-cyano-4-(2,2-dimethylpropylamino)quinolin-6-yl]carbamate
synonym: Example 1 [WO2020252151A1]
approved: f
ligand name: tilpisertib fosmecarbil
type: SyntheticOrganicLigand

edecesertib
isomeric SMILES: C(#N)[C@@H](C)Nc1c(cnc(c1)c1ccc2n1ncc(c2)C#N)C(=O)NC[C@H](C(C)(C)O)F
in ch i key: HORBHQPSWJRDSV-ZUOKHONESA-N
in ch i: InChI=1S/C22H22FN7O2/c1-13(8-24)29-17-7-18(19-5-4-15-6-14(9-25)10-28-30(15)19)26-11-16(17)21(31)27-12-20(23)22(2,3)32/h4-7,10-11,13,20,32H,12H2,1-3H3,(H,26,29)(H,27,31)/t13-,20-/m1/s1
comment: We obtained the chemical structure for edecesertib from the WHO's proposed INN list 127 (21 July 2022). In this document it was described as a serine/ threonine kinase inhibitor and antineoplastic. This Chemical structure mapped to PubChem CID 147817927, and to Example 3 in patent WO2020014468A1 which claims the examples as interleukin-1 receptor-associated kinase-4 (IRAK4) inhibitors <Reference id=43932/>. Based on Gilead's pipeline page they have an IRAK4 inhibitor GS-5718 in phase 1 development for potential in autoinflammatory diseases.
iupac name: 4-[[(1R)-1-cyanoethyl]amino]-6-(3-cyanopyrrolo[1,2-b]pyridazin-7-yl)-N-[(2R)-2-fluoro-3-hydroxy-3-methylbutyl]pyridine-3-carboxamide
approved: f
ligand name: edecesertib
type: SyntheticOrganicLigand

ulecaciclib
in ch i key: POFVJRKJJBFPII-UHFFFAOYSA-N
in ch i: InChI=1S/C25H33FN8S/c1-3-33-10-12-34(13-11-33)16-18-8-9-21(27-14-18)31-24-28-15-20(26)22(32-24)23-17(2)29-25(35-23)30-19-6-4-5-7-19/h8-9,14-15,19H,3-7,10-13,16H2,1-2H3,(H,29,30)(H,27,28,31,32)
comment: We obtained the chemical structure for ulecaciclib from the WHO's proposed INN list 127 (21 July 2022). In this document it was described as a cyclin-dependent kinase inhibitor and antineoplastic. This Chemical structure mapped to PubChem CID 126535127, and via ChEMBL to Tadesse et al.'s 2017 CDK4/6 inhibitor paper <Reference id=43931/>.
iupac name: N-cyclopentyl-5-[2-[[5-[(4-ethylpiperazin-1-yl)methyl]pyridin-2-yl]amino]-5-fluoropyrimidin-4-yl]-4-methyl-1,3-thiazol-2-amine
xref: CHEMBL4067549
synonym: compound 116 [PMID: 28156111]
approved: f
ligand name: ulecaciclib
type: SyntheticOrganicLigand

inixaciclib
in ch i key: YZSCPLGKKMSBMV-UHFFFAOYSA-N
in ch i: InChI=1S/C26H30F2N6O/c1-16(2)34-10-11-35-25-20(27)12-19(13-22(25)34)24-21(28)15-30-26(32-24)31-23-5-4-18(14-29-23)17-6-8-33(3)9-7-17/h4-5,12-17H,6-11H2,1-3H3,(H,29,30,31,32)
comment: We obtained the chemical structure for inixaciclib from the WHO's proposed INN list 127 (21 July 2022). In this document it was described as a cyclin-dependent kinase inhibitor and antineoplastic. This Chemical structure mapped to PubChem CID 139390026, and then to compound 442 in GiraFpharma's patent WO2019161224A1 which claims compounds as CDK4 or CDK6 inhibitors for use as anticancer drugs <Reference id=43930/>. We have been unable to map inixaciclib to a company research code.
iupac name: 5-fluoro-4-(8-fluoro-4-propan-2-yl-2,3-dihydro-1,4-benzoxazin-6-yl)-N-[5-(1-methylpiperidin-4-yl)pyridin-2-yl]pyrimidin-2-amine
synonym: compound 442 [WO2019161224A1]
synonym: example 50 [WO2019161224A1]
approved: f
ligand name: inixaciclib
type: SyntheticOrganicLigand

culmerciclib
in ch i key: LLFOBMRPWNABCB-UHFFFAOYSA-N
in ch i: InChI=1S/C24H27FN8/c1-15(2)23-18-12-16(4-6-20(18)31-32(23)3)22-19(25)14-28-24(30-22)29-21-7-5-17(13-27-21)33-10-8-26-9-11-33/h4-7,12-15,26H,8-11H2,1-3H3,(H,27,28,29,30)
comment: We obtained the chemical structure for culmerciclib from the WHO's proposed INN list 127 (21 July 2022). In this document it was described as a cyclin-dependent kinase inhibitor and antineoplastic. This Chemical structure mapped to PubChem CID 122544510, and to a structure in Nanjing Mingde New Drug Research and Development Company's patent WO2016141881A1 <Reference id=43929/> which claims selective CDK4/6 inhibitors as anticancer drugs.
iupac name: 5-fluoro-4-(2-methyl-3-propan-2-ylindazol-5-yl)-N-(5-piperazin-1-ylpyridin-2-yl)pyrimidin-2-amine
approved: f
ligand name: culmerciclib
type: SyntheticOrganicLigand

crozbaciclib
in ch i key: AEFFENQISAXIKE-UHFFFAOYSA-N
in ch i: InChI=1S/C28H30F2N6/c1-17-28(9-3-4-10-28)21-13-20(14-22(29)26(21)33-17)25-23(30)16-32-27(35-25)34-24-6-5-19(15-31-24)18-7-11-36(2)12-8-18/h5-6,13-16,18H,3-4,7-12H2,1-2H3,(H,31,32,34,35)
comment: We obtained the chemical structure for crozbaciclib from the WHO's proposed INN list 127 (21 July 2022). In this document it was described as a cyclin-dependent kinase inhibitor and antineoplastic. This Chemical structure mapped to PubChem CID 129202507 which has the synonym 'CDK4/6/1 Inhibitor, and via ChEMBL to compound 11 in Yin et al. (2018) <Reference id=43928/>. Compound 11 was optimised to cross the blood-brain barrier, and is intended as a therapy for glioblastoma multiforme.
iupac name: 5-fluoro-4-(7'-fluoro-2'-methylspiro[cyclopentane-1,3'-indole]-5'-yl)-N-[5-(1-methylpiperidin-4-yl)pyridin-2-yl]pyrimidin-2-amine
xref: CHEMBL4277900
approved: f
ligand name: crozbaciclib
type: SyntheticOrganicLigand

asnuciclib
in ch i key: GAIOPWBQKZMUNO-UHFFFAOYSA-N
comment: Asnuciclib (CDKI-73) is an orally bioavailable cyclin-dependent kinase 9 (CDK9) inhibitor that was developed for antineoplastic potential <Reference id=43926/><Reference id=43927/>. CDK9 plays a crucial role in the oncogenic transcription that's promoted by mixed-lineage leukemia gene (MLL) translocations in acute myeloid leukemia.
iupac name: 3-[[5-fluoro-4-[4-methyl-2-(methylamino)-1,3-thiazol-5-yl]pyrimidin-2-yl]amino]benzenesulfonamide
xref: CHEMBL2347597
synonym: CDKI-73
synonym: LS-007
synonym: compound 12e [PMID: 23301767]
approved: f
ligand name: asnuciclib
type: SyntheticOrganicLigand

camonsertib
in ch i key: YIHHYCIYAIVQKX-YNOVCBQDSA-N
in ch i: InChI=1S/C21H26N6O3/c1-13-12-29-7-6-26(13)19-8-17(21(28)9-14-2-3-15(10-21)30-14)16-11-23-27(20(16)24-19)18-4-5-22-25-18/h4-5,8,11,13-15,28H,2-3,6-7,9-10,12H2,1H3,(H,22,25)/t13-,14-,15+,21?/m1/s1
comment: RP-3500 is a clinical lead, selective ATR (Ataxia telangiectasia and Rad3-related) serine/threonine kinase inhibitor that was developed as a novel oncology therapeutic <Reference id=43922/>. We matched RP-3500's chemical structure to the INN 'camonsertib' that was included in the WHO's proposed INN list 127 (21 July 2022).
iupac name: (1R,5S)-3-[6-[(3R)-3-methylmorpholin-4-yl]-1-(1H-pyrazol-5-yl)pyrazolo[3,4-b]pyridin-4-yl]-8-oxabicyclo[3.2.1]octan-3-ol
synonym: RP3500
synonym: RP-3500
approved: f
ligand name: camonsertib
type: SyntheticOrganicLigand

RP-6306
in ch i key: FGSLKGDMSYOTPS-MRVPVSSYSA-N
in ch i: InChI=1S/C18H22N4O2/c1-8-5-6-13(23)10(3)15(8)22-16(19)14(17(20)24)12-7-9(2)11(4)21-18(12)22/h6-8,23H,5,19H2,1-4H3,(H2,20,24)/t8-/m1/s1
comment: RP-6306 is the first lead candidate in the class of protein kinase, membrane associated tyrosine/threonine 1 (PKMYT1) inhibitors to be advanced for clinical evaluation <Reference id=43920/>. It is orally bioavailable and selective for PKMYT1, and it is active in appropriate preclinical xenograft models of solid tumours <Reference id=43921/>. PKMYT1 is a negative regulator of CDK1, and its inhibition induces activation of CDK1 selectively in CCNE1-overexpressing cells; CCNE1 being a chromosome 19q12 locus that is amplified in multiple tumour types and which is a marker of poor prognosis and/or insensitivity to cytotoxic oncotherapies.
iupac name: (S)-2-Amino-1-(3-hydroxy-2,6-dimethylphenyl)-5,6-dimethyl-pyrrolo[2,3-b]pyridine-3-carboxamide
approved: f
ligand name: RP-6306
type: SyntheticOrganicLigand

allosteric modulator 33 [PMID: 35878399]
in ch i key: REDPQDQMPNUDEP-NXCFDTQHSA-N
comment: This compound acts as a positive allosteric modulator (activator) of the alpha isoform of protein kinase cGMP-dependent 1 (PKG1α) <Reference id=43916/>. It was designed as a pharmacological tool to explore the potential for exploiting PKG1α activation as a mechanism that would be applicable as a treatment for cardiovascular diseases. Compound 33 binds to an allosteric pocket that's proximal to PKG1α's low-affinity cGMP binding domain.
iupac name: 4-(((2S,3S)-3-((S)-1-(3,5-Dichlorophenyl)-2-hydroxyethoxy)-2-phenylpiperidin-1-yl)methyl)-3-nitrobenzoic Acid
synonym: compound 33 [PMID: 35878399]
approved: f
ligand name: allosteric modulator 33 [PMID: 35878399]
type: SyntheticOrganicLigand

VIC 1911
in ch i key: PLAVWQHGBMTMFR-UHFFFAOYSA-N
comment: VIC 1911 (formerly TAS 119) is an oral, small molecule Aurora kinase A-selective inhibitor. It is being progressed by Vitrac Therapeutics for anti-cancer potential.
iupac name: 1-(2,3-dichlorobenzoyl)-4-[[5-fluoro-6-[(5-methyl-1H-pyrazol-3-yl)amino]pyridin-2-yl]methyl]piperidine-4-carboxylic acid
xref: CHEMBL3692206
synonym: VIC1911
synonym: TAS-119
synonym: TAS119
synonym: example 1 [US10092556B2]
approved: f
ligand name: VIC 1911
type: SyntheticOrganicLigand

revaprazan
in ch i key: LECZXZOBEZITCL-UHFFFAOYSA-N
in ch i: InChI=1S/C22H23FN4/c1-14-15(2)24-22(25-19-10-8-18(23)9-11-19)26-21(14)27-13-12-17-6-4-5-7-20(17)16(27)3/h4-11,16H,12-13H2,1-3H3,(H,24,25,26)
comment: Revaprazan (YH-1885) is a K+-competitive acid blocker (P-CAB)/proton pump inhibitor <Reference id=43713/><Reference id=43714/>. First in human data demonstrating the on-target effect of revaprazan were reported in 2010 <Reference id=43715/>.
xref: CHEMBL1618279
synonym: YH-1885
synonym: YH1885
synonym: Revanex®
approved: t
ligand name: revaprazan
type: SyntheticOrganicLigand

SOS1 PROTAC 9d
in ch i key: AZBRWXRYNYEDKG-VWELVXIZSA-N
comment: This compound (9d) is a SOS1-directed PROTAC <Reference id=43908/>. It is a hybrid molecule combining a VHL ligand and a SOS1 agonist (from <Reference id=43909/>). Although the SOS1-interacting part of this PROTAC is an agonist it mediates efficient SOS1 protein degradation. In vitro 9d provides antiproliferative activity against human cancer cells with various KRAS mutations, and it inhibits tumour growth in a xenograft mouse model.
iupac name: (2S,4R)-1-[(2S)-2-[9-[4-[6-chloro-2-(2,6-diazaspiro[3.3]heptan-2-yl)-1-[(4-fluoro-3,5-dimethylphenyl)methyl]benzimidazol-4-yl]piperazin-1-yl]nonanoylamino]-3,3-dimethylbutanoyl]-4-hydroxy-N-[(1S)-1-[4-(4-methyl-1,3-thiazol-5-yl)phenyl]ethyl]pyrrolidine-2-carboxamide
approved: f
ligand name: SOS1 PROTAC 9d
type: SyntheticOrganicLigand

batoprotafib
in ch i key: UCJZOKGUEJUNIO-IINYFYTJSA-N
in ch i: InChI=1S/C18H24ClN7OS/c1-10-14(20)18(9-27-10)3-6-26(7-4-18)12-8-24-17(16(22)25-12)28-11-2-5-23-15(21)13(11)19/h2,5,8,10,14H,3-4,6-7,9,20H2,1H3,(H2,21,23)(H2,22,25)/t10-,14+/m0/s1
comment: TNO155 is an oral, allosteric inhibitor of SHP2 (a nonreceptor protein tyrosine phosphatase that's encoded by the PTPN11 gene) <Reference id=43907/>. SHP2 is an oncoprotein in its own right, but its inhibition is also being exploited to combat tumours that are driven by hyperactivation in the RAS-RAF-ERK signalling pathway. We matched TNO155's chemical structure to the INN 'batoprotafib' which was published in the WHO's proposed INN list 127 on 21 July 2022.
iupac name: (3S,4S)-8-[6-amino-5-(2-amino-3-chloropyridin-4-yl)sulfanylpyrazin-2-yl]-3-methyl-2-oxa-8-azaspiro[4.5]decan-4-amine
xref: CHEMBL4650521
synonym: TNO-155
synonym: compound 1 [PMID: 32910655]
synonym: TNO155
approved: f
ligand name: batoprotafib
type: SyntheticOrganicLigand

vociprotafib
in ch i key: HISJAYUQVHMWTA-BLLLJJGKSA-N
comment: RMC-4630 (Revolution Medicines) is a clinical stage oral, allosteric SHP2 (PTPN11) inhibitor <Reference id=43906/> that is being evaluated for efficacy against advanced solid tumours. SHP2 is a phosphatase whose inhibition blocks activation of the RAS-RAF-MEK-ERK signalling pathway which is often hyperactivated in tumours. We matched RMC-4630's chemical structure to the INN 'vociprotafib' which was released in the WHO's proposed INN list 127 on 21 July 2022.
iupac name: [6-(2-amino-3-chloropyridin-4-yl)sulfanyl-3-[(3S,4S)-4-amino-3-methyl-2-oxa-8-azaspiro[4.5]decan-8-yl]-5-methylpyrazin-2-yl]methanol
synonym: SHP2-IN-7
synonym: RMC4630
synonym: SAR442720
synonym: SAR-442720
synonym: compound A-290 [WO2018013597A1]
synonym: RMC-4630
approved: f
ligand name: vociprotafib
type: SyntheticOrganicLigand

LY3499446
in ch i key: YNBBKDMAVRSYRE-UHFFFAOYSA-N
comment: LY3499446 is a direct inhibitor of oncogenic KRAS mutant G12C that was developed for anticancer potential <Reference id=43902/>.
iupac name: 1-[4-[7-(2-amino-7-fluoro-1,3-benzothiazol-4-yl)-6-chloro-8-fluoroquinazolin-4-yl]piperazin-1-yl]prop-2-en-1-one
synonym: LY-3499446
synonym: compound B [WO2022002018A1]
approved: f
ligand name: LY3499446
type: SyntheticOrganicLigand

BI-167107
in ch i key: NWQXBEWHTDRJIP-UHFFFAOYSA-N
in ch i: InChI=1S/C21H26N2O4/c1-13-6-4-5-7-14(13)10-21(2,3)22-11-17(25)15-8-9-16(24)19-20(15)27-12-18(26)23-19/h4-9,17,22,24-25H,10-12H2,1-3H3,(H,23,26)
comment: BI-167107 is a β-adrenoceptor agonist <Reference id=43896/>.
iupac name: 5-hydroxy-8-[1-hydroxy-2-[[2-methyl-1-(2-methylphenyl)propan-2-yl]amino]ethyl]-4H-1,4-benzoxazin-3-one
xref: CHEMBL579394
synonym: BI167107
synonym: compound 6b [PMID: 19875286]
approved: f
ligand name: BI-167107
type: SyntheticOrganicLigand

danuglipron
in ch i key: HYBAKUMPISVZQP-DEOSSOPVSA-N
in ch i: InChI=1S/C31H30FN5O4/c32-25-14-20(16-33)4-5-23(25)19-41-30-3-1-2-26(35-30)21-8-11-36(12-9-21)18-29-34-27-7-6-22(31(38)39)15-28(27)37(29)17-24-10-13-40-24/h1-7,14-15,21,24H,8-13,17-19H2,(H,38,39)/t24-/m0/s1
comment: Danuglipron (PF-06882961) is a small molecule, non-peptide, orally active agonist of the human (and monkey) glucagon-like peptide-1 receptor (GLP-1R) <Reference id=41855/><Reference id=43828/>. It was developed as an alternative to established peptide GLP-1R agonists that are used to treat diabetes, and in some instances, obesity (e.g. <Ligand id=1133/> and <Ligand id=9724/>). Danuglipron appears to be a partial agonist in recruiting β-arrestin-2 to GLP-1R (EC50 490 nM) <Reference id=43828/>.
xref: CHEMBL4518483
synonym: PF-06882961
synonym: PF06882961
approved: f
ligand name: danuglipron
type: SyntheticOrganicLigand

metronidazole
canonical SMILES: OCCn1c(C)ncc1[N+](=O)[O-]
isomeric SMILES: OCCn1c(C)ncc1[N+](=O)[O-]
in ch i key: VAOCPAMSLUNLGC-UHFFFAOYSA-N
in ch i: InChI=1S/C6H9N3O3/c1-5-7-4-6(9(11)12)8(5)2-3-10/h4,10H,2-3H2,1H3
comment: Metronidazole is a synthetic nitroimidazole derivative that exhibits antiprotozoal and antibacterial (against anaerobic bacteria) activities. It also acts as a a radiosensitising agent in tumour cells.
iupac name: 2-(2-methyl-5-nitroimidazol-1-yl)ethanol
xref: CHEMBL137
synonym: Flagyl®
synonym: Metrogel®
synonym: BAY-5360
synonym: BAYER 5360
synonym: ROZEX®
approved: t
ligand name: metronidazole
type: SyntheticOrganicLigand

BMS-986141
in ch i key: KEEBLYWBELVGPQ-UHFFFAOYSA-N
in ch i: InChI=1S/C27H23N5O5S2/c1-31(2)25(33)16-7-5-15(6-8-16)24-28-17(14-38-24)13-36-21-9-18(34-3)10-22-19(21)11-23(37-22)20-12-32-26(29-20)39-27(30-32)35-4/h5-12,14H,13H2,1-4H3
comment: BMS-986141 is an orally active, selective, and reversible protease-activated receptor 4 (PAR4) antagonist with antiplatelet/antithrombotic activity <Reference id=43808/>. It was developed as a back-up to lead compound <Ligand id=10269/>.
iupac name: 4-[4-[[6-methoxy-2-(2-methoxyimidazo[2,1-b][1,3,4]thiadiazol-6-yl)-1-benzofuran-4-yl]oxymethyl]-1,3-thiazol-2-yl]-N,N-dimethylbenzamide
xref: CHEMBL3716552
synonym: BMS986141
synonym: compound 49 [PMID: 35729784]
approved: f
ligand name: BMS-986141
type: SyntheticOrganicLigand

peptide 22d
in ch i key: CPNJMMBLVDNJTP-GQUKTMJCSA-N
in ch i: InChI=1S/C44H58N12O9S/c1-3-25(2)38-43(63)49-31(20-27-22-46-29-12-6-5-11-28(27)29)40(60)50-33(44(64)56-17-8-13-34(56)42(62)48-30(39(45)59)21-36-52-54-55-53-36)24-66-19-16-26-10-4-7-14-35(26)65-18-9-15-37(58)47-32(23-57)41(61)51-38/h4-7,10-12,14,22,25,30-34,38,46,57H,3,8-9,13,15-21,23-24H2,1-2H3,(H2,45,59)(H,47,58)(H,48,62)(H,49,63)(H,50,60)(H,51,61)(H,52,53,54,55)/t25-,30-,31-,32-,33-,34-,38-/m0/s1
comment: This is a macrocyclic peptide that targets the STUB1 E3 ubiquitin ligase <Reference id=43893/>. 22d was developed from a short linear peptide (LWWPD) that binds STUB1 <Reference id=43894/>, to guide the design of more selective pharmacological inhibitors as tool compounds for target validation. Although 22d retains the binding affinity for STUB1 of the linear peptide, suboptimal cellular permeability means that this construct is not suitable for experiments in cells or in vivo.
approved: f
ligand name: peptide 22d
type: SyntheticOrganicLigand

compound 27 [PMID: 35834807]
in ch i key: LOQNSAZUXOBMAX-UHFFFAOYSA-N
in ch i: InChI=1S/C18H21N7O3/c19-16-20-13-11-12(1-2-14(13)28-16)15-21-17(24-3-7-26-8-4-24)23-18(22-15)25-5-9-27-10-6-25/h1-2,11H,3-10H2,(H2,19,20)
comment: This compound is a potent and selective inhibitor of the cancer therapeutic target, phosphoinositide-3-kinase α (PI3Kα) <Reference id=43882/>. It is orally bioavailable and has a long half-life (>10h), and it mediates an anti-gastric cancer effect in vivo.
iupac name: 6-(4,6-Dimorpholino-1,3,5-triazin-2-yl)benzo[d]oxazol-2-amine
approved: f
ligand name: compound 27 [PMID: 35834807]
type: SyntheticOrganicLigand

BI-3406
in ch i key: XVFDNRYZXDHTHT-PXAZEXFGSA-N
in ch i: InChI=1S/C23H25F3N4O3/c1-12(14-6-15(23(24,25)26)8-16(27)7-14)28-22-18-9-21(33-17-4-5-32-11-17)20(31-3)10-19(18)29-13(2)30-22/h6-10,12,17H,4-5,11,27H2,1-3H3,(H,28,29,30)/t12-,17+/m1/s1
comment: BI-3406 is a potent, selective, and orally bioavailable small-molecule that binds to the catalytic domain of SOS Ras/Rac guanine nucleotide exchange factor 1 (SOS1) and disrupts its interaction with KRAS <Reference id=43881/>. Blocking this protien-protein interaction is being explored as a novel mechanism to combat KRAS-driven cancers, and offers the advantage of providing anti-tumour activity that is independent of KRAS mutation status. BI-3406 is a useful molecular probe. It was further optimised to generate the clinical lead BI-1701963 (awaiting disclosure of chemical structure).
iupac name: N-[(1R)-1-[3-amino-5-(trifluoromethyl)phenyl]ethyl]-7-methoxy-2-methyl-6-[(3S)-oxolan-3-yl]oxyquinazolin-4-amine
xref: CHEMBL4519023
synonym: BI3406
approved: f
ligand name: BI-3406
type: SyntheticOrganicLigand

BT7480
in ch i key: DQYZLSMANMRIEI-BOFVMFDGSA-N
comment: BT7480 is a large molecule that consists of bi-cyclic peptide domains that interact with its target proteins CD137 (4-1BB; an immune cell co-activator molecule) and Nectin 4 (on certain cancer cells) <Reference id=43878/>. It engages two CD137 molecules for every one Nectin 4 molecule. This dual binding modality is being explored as a mechanism to induce a CD137-mediated immune cell response against Nectin 4-expressing tumour cells <Reference id=43879/>. BT7480 is therefore considered to represent a new modality for immuno-oncology. The SMILES string for BT7480's full chemical structure was provided within the Supporting Information for reference <Reference id=43878/>.
synonym: BT-7480
synonym: BCY11863
approved: f
ligand name: BT7480
type: PeptideLigand

(R)-STU104
in ch i key: OYJBHGSSAJNKJF-CQSZACIVSA-N
in ch i: InChI=1S/C18H18O4/c1-20-12-6-4-11(5-7-12)14-10-16(19)15-8-13(21-2)9-17(22-3)18(14)15/h4-9,14H,10H2,1-3H3/t14-/m1/s1
comment: (R)-STU104 is a first-in-class molecule that inhibits the interaction between the proteins kinases TAK1 (mitogen-activated protein kinase kinase kinase 7; MAP3K7) and MKK3 (mitogen-activated protein kinase kinase 3; MAP2K3) <Reference id=43711/>. These kinases are part of the inflammatory signalling cascade that culminates in TNF-α production. (R)-STU104 binds to MKK3 at a location that disrupts its interaction with the upstream kinase TAK1. This action perturbs MKK3 phosphorylation by TAK1 and inhibits downstream signal propagation. Blocking TAK1-mediated phosphorylation of MKK3 with (R)-STU104 reduces TNF-α in vitro and in mouse models of chronic ulcerative colitis (UC). In the mouse models (R)-STU104 was a more effective UC treatment than the approved UC drug <Ligand id=2700/> (a PPARγ inhibitor). In addition to TNF-α, (R)-STU104 reduced production of several pro-inflammatory cytokines in vivo, including IL-1β, IL-6, and IL-23.
iupac name: (3R)-4,6-dimethoxy-3-(4-methoxyphenyl)-2,3-dihydroinden-1-one
synonym: (R)-4e [PMID: 35442672]
approved: f
ligand name: (R)-STU104
type: SyntheticOrganicLigand

compound 23 [PMID: 35816678]
in ch i key: CIPXFTLGPVQJKN-HUUCEWRRSA-N
in ch i: InChI=1S/C20H25FN4O2/c1-14-13-24(19-7-8-22-12-18(19)21)9-10-25(14)20(26)23-15(2)16-5-4-6-17(11-16)27-3/h4-8,11-12,14-15H,9-10,13H2,1-3H3,(H,23,26)/t14-,15-/m1/s1
comment: This small molecule is a potent Rho kinase (ROCK) inhibitor <Reference id=43877/>. It was designed to be selective and to cross the blood-brain barrier, in order to evaluate the potential of ROCK inhibition as a disease modifier in Huntington's disease, since ROCK has been implicated in mutant huntingtin protein's aggregation and neurotoxic effects.
iupac name: (2R)-4-(3-fluoropyridin-4-yl)-N-[(1R)-1-(3-methoxyphenyl)ethyl]-2-methylpiperazine-1-carboxamide
approved: f
ligand name: compound 23 [PMID: 35816678]
type: SyntheticOrganicLigand

2-Methoxyestradiol
in ch i key: CQOQDQWUFQDJMK-SSTWWWIQSA-N
in ch i: InChI=1S/C19H26O3/c1-19-8-7-12-13(15(19)5-6-18(19)21)4-3-11-9-16(20)17(22-2)10-14(11)12/h9-10,12-13,15,18,20-21H,3-8H2,1-2H3/t12-,13+,15-,18-,19-/m0/s1
comment: 2-Methoxyestradiol is a high-affinity agonist of the G protein-coupled estrogen receptor (GPER) <Reference id=28004/><Reference id=43869/>. It is an endogenous metabolite of estradiol (<Ligand id=1013/>) and 2-hydroxyestradiol. 2-Methoxyestradiol has anti-angogenic and vasodilatory activities <Reference id=43870/><Reference id=43871/><Reference id=43872/>, but it has limited oral bioavailability <Reference id=43874/><Reference id=43876/> and failed to show significant efficacy in clinical trials.
iupac name: (8R,9S,13S,14S,17S)-2-methoxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-3,17-diol
xref: CHEMBL299613
synonym: 2-ME2
synonym: 2-MeO-E2
synonym: Panzem®
synonym: NSC-659853
synonym: 2ME2
approved: f
ligand name: 2-Methoxyestradiol
type: MetaboliteLigand

TP0556351
in ch i key: FVDPKGPPYGTKTO-DLXWRWKMSA-N
in ch i: InChI=1S/C50H70N10O16/c1-28(2)25-37(49(74)59(3)38(18-20-42(65)66)50(75)60-24-6-7-31(60)26-39(52)61)58-47(72)35(21-22-51)56-48(73)36(27-43(67)68)57-46(71)34(17-19-41(63)64)55-40(62)8-4-5-23-54-45(70)30-11-15-33(16-12-30)76-32-13-9-29(10-14-32)44(53)69/h9-16,28,31,34-38H,4-8,17-27,51H2,1-3H3,(H2,52,61)(H2,53,69)(H,54,70)(H,55,62)(H,56,73)(H,57,71)(H,58,72)(H,63,64)(H,65,66)(H,67,68)/t31-,34-,35-,36-,37-,38-/m0/s1
comment: TP0556351 is a synthetic hexapeptide molecule that is a selective inhibitor of the anti-fibrosis drug target matrix metallopeptidase 2 (MMP2) <Reference id=43867/>.
iupac name: (4S)-5-[[(2S)-1-[[(2S)-4-amino-1-[[(2S)-1-[[(2S)-1-[(2S)-2-(2-amino-2-oxoethyl)pyrrolidin-1-yl]-4-carboxy-1-oxobutan-2-yl]-methylamino]-4-methyl-1-oxopentan-2-yl]amino]-1-oxobutan-2-yl]amino]-3-carboxy-1-oxopropan-2-yl]amino]-4-[5-[[4-(4-carbamoylphenoxy)benzoyl]amino]pentanoylamino]-5-oxopentanoic acid
synonym: compound 9 [PMID: 35687819]
synonym: TP-0556351
approved: f
ligand name: TP0556351
type: PeptideLigand

maresin 1
canonical SMILES: CC/C=C/C/C=C/C[C@@H](/C=C/C=C/C=C/[C@@H](C/C=C/CCC(=O)O)O)O
isomeric SMILES: CC/C=C/C/C=C/C[C@@H](/C=C/C=C/C=C/[C@@H](C/C=C/CCC(=O)O)O)O
in ch i key: HLHYXXBCQOUTGK-LUSCUACYSA-N
in ch i: InChI=1S/C22H32O4/c1-2-3-4-5-6-10-15-20(23)16-11-7-8-12-17-21(24)18-13-9-14-19-22(25)26/h3-4,6-13,16-17,20-21,23-24H,2,5,14-15,18-19H2,1H3,(H,25,26)/b4-3-,8-7+,10-6-,13-9-,16-11+,17-12+/t20-,21-/m0/s1
comment: Maresins are anti-inflammatory and pro-resolving lipid mediators that are biosynthesised from <Ligand id=1051/> (DHA; an omega-3 fatty acid) by macrophages. Maresin 1 was the first family member to be identified <Reference id=43864/><Reference id=43865/>.
iupac name: (4Z,7R,8E,10E,12Z,14S,16Z,19Z)-7,14-dihydroxydocosa-4,8,10,12,16,19-hexaenoic acid
synonym: Maresin-1
synonym: MaR1
synonym: 7R-Maresin 1
synonym: 7R,14S-dihydroxydocosa-4Z,8E,10E,12Z,16Z,19Z-hexaenoic acid
approved: f
ligand name: maresin 1
type: SyntheticOrganicLigand

maresin 2
canonical SMILES: CC/C=C/C/C=C/C[C@@H]([C@@H](/C=C/C=C/C=C/C/C=C/CCC(=O)O)O)O
isomeric SMILES: CC/C=C/C/C=C/C[C@@H]([C@@H](/C=C/C=C/C=C/C/C=C/CCC(=O)O)O)O
in ch i key: ALWYOLKNLLFCAY-GYROAIJESA-N
in ch i: InChI=1S/C22H32O4/c1-2-3-4-5-11-14-17-20(23)21(24)18-15-12-9-7-6-8-10-13-16-19-22(25)26/h3-4,6-7,9-15,18,20-21,23-24H,2,5,8,16-17,19H2,1H3,(H,25,26)/b4-3-,7-6-,12-9+,13-10-,14-11-,18-15+/t20-,21+/m0/s1
comment: Maresins are anti-inflammatory and pro-resolving lipid mediators that are biosynthesised from <Ligand id=1051/> (DHA) by macrophages, via conversions that are catalysed by12-LOX and soluble epoxide hydrolase (sEH). Maresin 2 was identified in 2014 <Reference id=43857/>.
iupac name: (4Z,7Z,9E,11E,13R,14S,16Z,19Z)-13,14-dihydroxydocosa-4,7,9,11,16,19-hexaenoic acid
synonym: 13R,14S-dihydroxy-docosahexaenoic acid
synonym: 13R,14S-diHDHA
synonym: maresin-2
synonym: MaR2
approved: f
ligand name: maresin 2
type: SyntheticOrganicLigand

efavirenz
canonical SMILES: FC([C@@]1(C#CC2CC2)OC(=O)Nc2c1cc(Cl)cc2)(F)F
isomeric SMILES: FC([C@@]1(C#CC2CC2)OC(=O)Nc2c1cc(Cl)cc2)(F)F
in ch i key: XPOQHMRABVBWPR-ZDUSSCGKSA-N
in ch i: InChI=1S/C14H9ClF3NO2/c15-9-3-4-11-10(7-9)13(14(16,17)18,21-12(20)19-11)6-5-8-1-2-8/h3-4,7-8H,1-2H2,(H,19,20)/t13-/m0/s1
comment: Efavirenz is an antiviral drug that is used in the treatment of HIV. It is a synthetic non-nucleoside inhibitor (NNRTI) that binds to the HIV RNA-dependent DNA polymerase and thereby blocks viral DNA replication <Reference id=40767/>.
iupac name: (4S)-6-chloro-4-(2-cyclopropylethynyl)-4-(trifluoromethyl)-1H-3,1-benzoxazin-2-one
xref: CHEMBL223228
synonym: Sustiva®
synonym: EFV
synonym: DMP-266
synonym: DMP266
synonym: Stocrin®
synonym: L-743726
synonym: L-743,726
approved: t
ligand name: efavirenz
type: SyntheticOrganicLigand

SAGE-718
in ch i key: BVBRUQYHUXKZMQ-JNVAYQLDSA-N
in ch i: InChI=1S/C27H43F3O2/c1-17(10-13-26(5,32)27(28,29)30)20-8-9-21-19-7-6-18-16-23(2,31)14-15-24(18,3)22(19)11-12-25(20,21)4/h6,17,19-22,31-32H,7-16H2,1-5H3/t17-,19+,20-,21+,22+,23+,24+,25-,26+/m1/s1
comment: SAGE-718 is a positive allosteric modulator (PAM) of N-Methyl-D-aspartate (NMDA) receptors that was designed as a potential treatment for cognitive impairment <Reference id=43845/>. Its pharmacokinetics support oral dosing.
iupac name: (3S,8S,9S,10R,13R,14S,17R)-3,10,13-trimethyl-17-[(2R,5S)-6,6,6-trifluoro-5-hydroxy-5-methylhexan-2-yl]-1,2,4,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-ol
synonym: SAGE718
synonym: compound 5 [PMID: 35785990]
approved: f
ligand name: SAGE-718
type: SyntheticOrganicLigand

maribavir
in ch i key: KJFBVJALEQWJBS-XUXIUFHCSA-N
comment: Maribavir is an orally bioavailable benzimidazole L-riboside that inhibits cytomegalovirus (CMV) pUL97 kinase with nM potency in vitro <Reference id=43842/>. It inhibits viral replication.
iupac name: (2S,3S,4R,5S)-2-[5,6-dichloro-2-(propan-2-ylamino)benzimidazol-1-yl]-5-(hydroxymethyl)oxolane-3,4-diol
xref: CHEMBL515408
synonym: Camvia®
synonym: benzimidavir
synonym: G1263
synonym: GW-1263
synonym: 1263W94
synonym: Livtencity®
approved: t
ligand name: maribavir
type: SyntheticOrganicLigand

compound 13 [PMID: 35653642]
in ch i key: SBHYXGMXVZWIKR-UHFFFAOYSA-N
in ch i: InChI=1S/C31H27N7O5/c1-33-27(39)21-9-14-23(15-10-21)34-30-36-29(32)38(37-30)31(42)35-24-12-7-20(8-13-24)22-11-16-26(25(17-22)28(40)41)43-18-19-5-3-2-4-6-19/h2-17H,18H2,1H3,(H,33,39)(H,35,42)(H,40,41)(H3,32,34,36,37)
comment: This is a small molecule that was optimised for binding to the pseudokinase (JH2) domain of Janus kinase 2 (JAK2) <Reference id=43832/>. It is ~200-fold selective for JH2 compared to the JH1 active kinase site of the enzyme. It binds potently to the JH2 domain with the V617F mutation (Kd 43 nM) that is a known driver of pathogenesis in some myeloproliferative neoplasms. Compound 13 is slightly less permeable than <Ligand id=12047/>, but is active in cellular assays, whereas compound 11 is inactive in these assays.
iupac name: 4′-(5-Amino-3-((4-(methylcarbamoyl)phenyl)amino)-1H-1,2,4-triazole-1-carboxamido)-4-(benzyloxy)-[1,1′-biphenyl]-3-carboxylic acid
approved: f
ligand name: compound 13 [PMID: 35653642]
type: SyntheticOrganicLigand

compound 11 [PMID: 35653642]
in ch i key: KMNBCUUTUMNJGS-UHFFFAOYSA-N
in ch i: InChI=1S/C29H25N7O6S/c30-27-34-28(32-21-11-13-23(14-12-21)43(31,40)41)35-36(27)29(39)33-22-9-6-19(7-10-22)20-8-15-25(24(16-20)26(37)38)42-17-18-4-2-1-3-5-18/h1-16H,17H2,(H,33,39)(H,37,38)(H2,31,40,41)(H3,30,32,34,35)
comment: This is a small molecule that was optimised for binding to the pseudokinase (JH2) domain of Janus kinase 2 (JAK2) <Reference id=43832/>. It is ~150-fold selective for JH2 compared to the JH1 active kinase site of the enzyme. It binds potently to the JH2 domain with the V617F mutation (Kd 62 nM) that is a known driver of pathogenesis in some myeloproliferative neoplasms. Compound 11 is a potent binder of JAK2 JH2 but it is inactive in cellular assays.
iupac name: 5-[4-[[5-amino-3-(4-sulfamoylanilino)-1,2,4-triazole-1-carbonyl]amino]phenyl]-2-phenylmethoxybenzoic acid
approved: f
ligand name: compound 11 [PMID: 35653642]
type: SyntheticOrganicLigand

cefozopran
isomeric SMILES: CO/N=C(/c1nsc(n1)N)/C(=O)N[C@H]1[C@@H]2N(C1=O)C(=C(CS2)C[n+]1c2cccnn2cc1)C(=O)[O-]
in ch i key: QDUIJCOKQCCXQY-WHJQOFBOSA-N
in ch i: InChI=1S/C19H17N9O5S2/c1-33-24-11(14-23-19(20)35-25-14)15(29)22-12-16(30)28-13(18(31)32)9(8-34-17(12)28)7-26-5-6-27-10(26)3-2-4-21-27/h2-6,12,17H,7-8H2,1H3,(H3-,20,22,23,25,29,31,32)/b24-11-/t12-,17-/m1/s1
comment: Cefozopran is a fourth generation cephalosporin, belonging to the β-lactam class of antibacterial compounds. It has broad-spectrum activity and was developed by Takeda for parenteral treatment of infections caused by a range of Gram-positive and Gram-negative bacteria <Reference id=43886/><Reference id=43887/>.
iupac name: (6R,7R)-7-[[(2Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-methoxyiminoacetyl]amino]-3-(imidazo[2,3-f]pyridazin-4-ium-1-ylmethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
xref: CHEMBL1276663
synonym: SCE-2787
approved: t
ligand name: cefozopran
type: SyntheticOrganicLigand

compound 23 [PMID: 35767390]
in ch i key: CQKVACARDGYEMU-VWLOTQADSA-N
in ch i: InChI=1S/C27H34N6O2/c1-15(2)33-22(13-14-28-33)26(34)30-25(24(19-5-6-19)20-7-8-20)27(35)29-21-11-9-18(10-12-21)23-16(3)31-32-17(23)4/h9-15,19-20,24-25H,5-8H2,1-4H3,(H,29,35)(H,30,34)(H,31,32)/t25-/m0/s1
comment: This is a small synthetic molecule that has been demonstrated to disrupt the interaction between the two monomer peptides of the functional interleukin 17A (IL-17A) homodimer (IL-17AA) <Reference id=43830/>. Compound 23 was designed as an orally bioavailable agent, for potential to disrupt IL-17A signalling via the IL-17 receptor (principally the IL-17RA/IL-17RC heterodimer), to induce an anti-inflammatory effect in diseases like psoriasis, which are driven by abnormally high IL-17AA expression levels. The 3D structure of compound 23 in complex with the human IL-17AA dimer has been resolved by X-ray crystallography (PDB ID 7AMA). The chemical and physical properties of compound 23 satisfy Lipinski's rule of five for druglikeness <Reference id=43831/>.
synonym: IL-17 modulator 4
approved: f
ligand name: compound 23 [PMID: 35767390]
type: SyntheticOrganicLigand

BOP
in ch i key: PNMINTLPFWMZKM-VROPFNGYSA-M
in ch i: InChI=1S/C25H29N3O7S.Na/c29-23(22-9-6-16-28(22)36(33,34)20-7-2-1-3-8-20)26-21(24(30)31)17-18-10-12-19(13-11-18)35-25(32)27-14-4-5-15-27;/h1-3,7-8,10-13,21-22H,4-6,9,14-17H2,(H,26,29)(H,30,31);/q;+1/p-1/t21-,22-;/m0./s1
comment: This modified dipeptide is used as an antagonist of the α9β1 and α4β1 integrins functions <Reference id=43826/><Reference id=43825/>. It is used experimentally as the sodium salt.
iupac name: (2S)-2-[[(2S)-1-(benzenesulfonyl)pyrrolidine-2-carbonyl]amino]-3-[4-(pyrrolidine-1-carbonyloxy)phenyl]propanoic acid
xref: CHEMBL288474
synonym: compound 2 [PMID: 24363056]
synonym: N-(Benzenesulfonyl)-L-prolyl-L-O-(1-pyrrolidinylcarbonyl)tyrosine
synonym: compound 3 [PMID: 12033947]
approved: f
ligand name: BOP
type: PeptideLigand

compound 58 [WO2021252491A1]
in ch i key: YRZQYTTUZBVUFK-KVAWWVGVSA-N
in ch i: InChI=1S/C25H32N4O7S/c30-22-15(7-4-10-26-22)12-20(25(33)37(34,35)36)28-23(31)21-17-8-3-6-16(17)13-29(21)24(32)19-11-14-5-1-2-9-18(14)27-19/h1-2,5,9,11,15-17,20-21,25,27,33H,3-4,6-8,10,12-13H2,(H,26,30)(H,28,31)(H,34,35,36)/t15-,16-,17-,20-,21-,25?/m0/s1
comment: This compound is one of the SARS-CoV-2 main protease (Mpro) inhibitors claimed in patent WO2021252491A1 from Aligos Therapeutics and Katholieke Universiteit Leuven <Reference id=43817/>. We selected this example (58) for its combination of potency against SARS-CoV-2 Mpro enzymatic activity, and its ability to inhibit SARS-CoV-2 infection with relatively low cytotoxicity against model cell lines in vitro. Aligos Therapeutics have declared ALG-097558 as their lead clinical candidate SARS-CoV-2 antiviral, but have not yet disclosed its chemical structure (June 2022). Aligos have also published in vitro data (inhibition of SARS-CoV-2 infection in the Syrian hamster model) for another Mpro inhibitor, ALG-097111 <Reference id=43818/>, but again no complete chemical structure was divulged.
iupac name: (2S)-2-{[(1S,3aR,6aS)-2-(1H-indole-2-carbonyl)-octahydrocyclopenta[c]pyrrol-1-yl]formamido}-1-hydroxy-3-[(3S)-2-oxopiperidin-3-yl]propane-1-sulfonic acid
approved: f
ligand name: compound 58 [WO2021252491A1]
type: SyntheticOrganicLigand

example 10 [WO2022129953]
in ch i key: BIIBYWQGRFWQKM-JVVROLKMSA-N
comment: This compound is one of the most potent SARS-CoV-2 Mpro inhibitors in Heptares' patent WO2022129953 <Reference id=43816/>. We suspect that their clinical lead SH-879 might be claimed in this patent, but its chemical structure has not been disclosed (June 2022).
iupac name: (2S)-N-[1-(cyclopropylcarbamoyl)-1-oxo-3-[(3S)-2-oxopyrrolidin-3-yl]propan-2-yl]-2-[(2E)-3-(2,4-dichlorophenyl)prop-2-enamido]-4,4-dimethylpentanamide
approved: f
ligand name: example 10 [WO2022129953]
type: SyntheticOrganicLigand

example 37 [WO2022021841A1]
in ch i key: FIOKKXQKMFIASF-NAQAXNRLSA-N
in ch i: InChI=1S/C24H30FN3O4/c25-18-5-1-3-15(11-18)7-8-21(30)28-13-17-4-2-6-20(17)22(28)24(32)27-19(14-29)12-16-9-10-26-23(16)31/h1,3,5,11,14,16-17,19-20,22H,2,4,6-10,12-13H2,(H,26,31)(H,27,32)/t16-,17-,19-,20-,22?/m0/s1
comment: This is one of the most potent SARS-CoV-2 Mpro inhibitors that are claimed in patent WO2022021841A1 (Sichuan University) <Reference id=43815/>.
approved: f
ligand name: example 37 [WO2022021841A1]
type: SyntheticOrganicLigand

ocedurenone
in ch i key: UXHQLGLGLZKHTC-CUNXSJBXSA-N
in ch i: InChI=1S/C28H30ClN5O2/c29-23-15-19(6-5-18(23)16-30)34-27(17-3-1-2-4-17)22-8-9-24-21(26(22)32-34)7-10-25(31-24)28(36)33-13-11-20(35)12-14-33/h5-7,10,15,17,20,22,27,35H,1-4,8-9,11-14H2/t22-,27-/m0/s1
comment: Ocedurenone (KBP-5074) is a selective and potent non-steroidal mineralocorticoid receptor (MR) antagonist that was developed by KBP Biosciences for management of uncontrolled/resistant hypertension in advanced chronic kidney disease <Reference id=43813/>. The non-steroidal MR antagonist class of drugs includes <Ligand id=8678/> and <Ligand id=9894/> which are already in clinical use. These agents typically demonstrate a lower risk of inducing hyperkalemia <Reference id=43812/><Reference id=28997/> and with reduced hormonal side effects compared to steroidal MR antagonists such as <Ligand id=2875/> and <Ligand id=2876/>. The chemical structure for KBP-5074 that's depicted here, was disclosed in <Reference id=43813/>, and is the (3S,3aR) enantiomer, and this matches the structure submitted for the INN ocedurenone. This chemical structure is one of those claimed in KBP Biosciences' patent US9468635B2 (Example 12 therein) <Reference id=43814/>.
iupac name: 4-[(3S,3aR)-3-cyclopentyl-7-(4-hydroxypiperidine-1-carbonyl)-3,3a,4,5-tetrahydropyrazolo[3,4-f]quinolin-2-yl]-2-chlorobenzonitrile
synonym: KBP5074
synonym: KBP-5074
synonym: Example 12 [US9468635B2]
approved: f
ligand name: ocedurenone
type: SyntheticOrganicLigand

apararenone
in ch i key: AZNHWXAFPBYFGH-UHFFFAOYSA-N
in ch i: InChI=1S/C17H17FN2O4S/c1-17(2)16(21)20(13-7-4-11(18)5-8-13)14-9-6-12(10-15(14)24-17)19-25(3,22)23/h4-10,19H,1-3H3
comment: Apararenone (MT-3995) is a selective and potent non-steroidal mineralocorticoid receptor (MR) antagonist <Reference id=43809/>. It was developed to counteract MR-induced hypertension and organ damage in diseases including diabetic nephropathy and NASH.
xref: CHEMBL2181929
synonym: compound 39 [PMID: 35652647]
synonym: MT-3995
synonym: MT3995
approved: f
ligand name: apararenone
type: SyntheticOrganicLigand

methenamine
canonical SMILES: C1N2CN3CN1CN(C2)C3
isomeric SMILES: C1N2CN3CN1CN(C2)C3
in ch i key: VKYKSIONXSXAKP-UHFFFAOYSA-N
in ch i: InChI=1S/C6H12N4/c1-7-2-9-4-8(1)5-10(3-7)6-9/h1-6H2
comment: Methenamine is a heterocyclic organic compound. It is metabolised to formaldehyde, which acts as a nonspecific bactericidal agent. Methenamine is administered as the hippuric acid salt, methenamine hippurate (PubChem CID 21945).
xref: CHEMBL1201270
synonym: Hiprex®
synonym: Mandelamine®
synonym: Urex®
approved: t
ligand name: methenamine
type: SyntheticOrganicLigand

UE2343
in ch i key: MMZFGTAMARVHAF-RTHVDDQRSA-N
in ch i: InChI=1S/C19H19N5O2S/c25-17(12-6-16(27-11-12)13-9-22-23-10-13)24-14-2-3-15(24)8-19(26,7-14)18-20-4-1-5-21-18/h1,4-6,9-11,14-15,26H,2-3,7-8H2,(H,22,23)/t14-,15+,19?
comment: UE2343 is an oral, brain-penetrant hydroxysteroid 11-beta dehydrogenase 1 (11-βHSD1) inhibitor that was developed to reduce brain levels of the stress hormone cortisol, as a mechanism to improve memory in Alzheimer's disease patients <Reference id=43804/><Reference id=43805/>. It failed to provide efficacy in a phase 2 clinical trial.
iupac name: [(1S,5R)-3-hydroxy-3-pyrimidin-2-yl-8-azabicyclo[3.2.1]octan-8-yl]-[5-(1H-pyrazol-4-yl)thiophen-3-yl]methanone
synonym: Xanamem®
synonym: UE-2343
synonym: compound 4 [PMID: 28012176]
approved: f
ligand name: UE2343
type: SyntheticOrganicLigand

compound 1 [PMID: 24793884]
canonical SMILES: CCOC(=O)c1sc(nc1O)c1ccncc1
isomeric SMILES: CCOC(=O)c1sc(nc1O)c1ccncc1
in ch i key: SHVRAFGUKKOKIO-UHFFFAOYSA-N
in ch i: InChI=1S/C11H10N2O3S/c1-2-16-11(15)8-9(14)13-10(17-8)7-3-5-12-6-4-7/h3-6,14H,2H2,1H3
comment: Compound 1 is one of the analogues assessed in <Reference id=27038/> as a potential cell division cycle 7 (cdc7) inhibitor.
iupac name: ethyl 4-hydroxy-2-(pyridin-4-yl)-1,3-thiazole-5-carboxylate
xref: CHEMBL3261228
approved: f
ligand name: compound 1 [PMID: 24793884]
type: SyntheticOrganicLigand

cefpirome
isomeric SMILES: CO/N=C(/c1csc(n1)N)/C(=O)N[C@H]1[C@@H]2N(C1=O)C(=C(CS2)C[n+]1cccc2c1CCC2)C(=O)[O-]
in ch i key: DKOQGJHPHLTOJR-WHRDSVKCSA-N
in ch i: InChI=1S/C22H22N6O5S2/c1-33-26-15(13-10-35-22(23)24-13)18(29)25-16-19(30)28-17(21(31)32)12(9-34-20(16)28)8-27-7-3-5-11-4-2-6-14(11)27/h3,5,7,10,16,20H,2,4,6,8-9H2,1H3,(H3-,23,24,25,29,31,32)/b26-15-/t16-,20-/m1/s1
comment: Cefpirome is a semisynthetic, fourth generation cephalosporin belonging to the β-lactam class of antibacterial compounds <Reference id=43771/>.
iupac name: (6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-(6,7-dihydro-5H-cyclopenta[b]pyridin-1-ium-1-ylmethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
xref: CHEMBL65794
synonym: HR 810
synonym: HR-810
synonym: Romecef®
approved: t
ligand name: cefpirome
type: SyntheticOrganicLigand

cefoselis
canonical SMILES: OCCn1c(N)cc[n+]1CC1=C(C(=O)[O-])N2[C@H](SC1)[C@@H](C2=O)NC(=O)/C(=N/OC)/c1csc(n1)N
isomeric SMILES: CO/N=C(/c1csc(n1)N)/C(=O)N[C@H]1[C@@H]2N(C1=O)C(=C(CS2)C[n+]1ccc(n1CCO)N)C(=O)[O-]
in ch i key: BHXLLRXDAYEMPP-SBGRAJFYSA-N
in ch i: InChI=1S/C19H22N8O6S2/c1-33-24-12(10-8-35-19(21)22-10)15(29)23-13-16(30)27-14(18(31)32)9(7-34-17(13)27)6-25-3-2-11(20)26(25)4-5-28/h2-3,8,13,17,20,28H,4-7H2,1H3,(H4,21,22,23,29,31,32)/b24-12-/t13-,17-/m1/s1
comment: Cefoselis is a semisynthetic, fourth generation cephalosporin belonging to the β-lactam class of antibacterial compounds.
iupac name: (6R,7R)-3-[[3-amino-2-(2-hydroxyethyl)pyrazol-1-ium-1-yl]methyl]-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
xref: CHEMBL2105940
synonym: FK037
synonym: FK-037
synonym: FK 037
synonym: Wincef®
approved: t
ligand name: cefoselis
type: SyntheticOrganicLigand

compound 16g [PMID: 35507418]
in ch i key: CRBPLLHXFFMVKV-UHFFFAOYSA-N
in ch i: InChI=1S/C29H25FN2O8/c1-14-7-16(25(35)17-9-18(30)11-20(10-17)38-3)8-15(2)27(14)40-19-5-6-21-22(12-19)29(39-4)32-24(26(21)36)28(37)31-13-23(33)34/h5-12,36H,13H2,1-4H3,(H,31,37)(H,33,34)
comment: This compound is reported as a thyroid receptor β (THRβ)-selective agonist <Reference id=43759/>. It activates the wild type receptor and the subfunctional mutant receptor THRβH435R which has impaired sensitivity to thyroid hormones and underlies resistance to thyroid hormone in carriers.
iupac name: (7-(4-(3-Fluoro-5-methoxybenzoyl)-2,6-dimethylphenoxy)-4-hydroxy-1-methoxyisoquinoline-3-carbonyl)glycine
approved: f
ligand name: compound 16g [PMID: 35507418]
type: SyntheticOrganicLigand

resmetirom
in ch i key: FDBYIYFVSAHJLY-UHFFFAOYSA-N
comment: Resmetirom (MGL-3196) was developed as a thyroid receptor β (THRβ)-selective agonist, for potential to treat non-alcoholic steatohepatitis (NASH) and heterozygous familial hypercholesterolemia, with reduced potential to cause side-effects associated with THRα activation outside the liver <Reference id=43758/>.
iupac name: 2-[3,5-dichloro-4-[(6-oxo-5-propan-2-yl-1H-pyridazin-3-yl)oxy]phenyl]-3,5-dioxo-1,2,4-triazine-6-carbonitrile
xref: CHEMBL3261331
synonym: MGL-3196
synonym: MGL3196
synonym: compound 53 [PMID: 24712661]
synonym: VIA-3196
synonym: VIA3196
approved: f
ligand name: resmetirom
type: SyntheticOrganicLigand

biapenem
in ch i key: MRMBZHPJVKCOMA-YJFSRANCSA-N
comment: Biapenem is a β-lactam (carbapenem), with broad-spectrum antibacterial activity <Reference id=43748/><Reference id=43749/>.
iupac name: (4R,5S,6S)-3-(6,7-dihydro-5H-pyrazolo[1,2-a][1,2,4]triazol-4-ium-6-ylsulfanyl)-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate
xref: CHEMBL285347
synonym: L-627
synonym: Omegacin®
synonym: LJC10,627
synonym: RPX2003
synonym: LJC 10,627
synonym: L 627
synonym: LJC-10627
synonym: LJC 10627
approved: t
ligand name: biapenem
type: SyntheticOrganicLigand

novobiocin
in ch i key: YJQPYGGHQPGBLI-KGSXXDOSSA-N
in ch i: InChI=1S/C31H36N2O11/c1-14(2)7-8-16-13-17(9-11-19(16)34)27(37)33-21-22(35)18-10-12-20(15(3)24(18)42-28(21)38)41-29-23(36)25(43-30(32)39)26(40-6)31(4,5)44-29/h7,9-13,23,25-26,29,34-36H,8H2,1-6H3,(H2,32,39)(H,33,37)/t23-,25+,26-,29-/m1/s1
comment: Novobiocin was originally isolated from the actinomycete Streptomyces niveus and belongs to the aminocoumarins, a class of compounds characterized by a 3-amino-4,7-dihydroxycoumarin ring. It is effective against Gram-positive bacteria but has limited activity against Gram-negative pathogens.
iupac name: [(3R,4S,5R,6R)-5-hydroxy-6-[4-hydroxy-3-[[4-hydroxy-3-(3-methylbut-2-enyl)benzoyl]amino]-8-methyl-2-oxochromen-7-yl]oxy-3-methoxy-2,2-dimethyloxan-4-yl] carbamate
xref: CHEMBL36506
synonym: cathomycin
synonym: streptonivicin
synonym: Albamycin®
synonym: PA 93
synonym: cardelmycin
approved: t
ligand name: novobiocin
type: NaturalProductLigand

Wnt-C59
in ch i key: KHZOJCQBHJUJFY-UHFFFAOYSA-N
in ch i: InChI=1S/C25H21N3O/c1-18-15-22(12-14-27-18)20-6-4-19(5-7-20)16-25(29)28-24-10-8-21(9-11-24)23-3-2-13-26-17-23/h2-15,17H,16H2,1H3,(H,28,29)
comment: Wnt-C59 is an experimental inhibitor of the membrane bound O-acyl transferase, porcupine (PORCN) <Reference id=40114/>. Procupine catalyses crucial Wnt ligand palmitoylation, and it is an active therapeutic molecular target.
iupac name: 2-[4-(2-methylpyridin-4-yl)phenyl]-N-(4-pyridin-3-ylphenyl)acetamide
xref: CHEMBL2139947
approved: f
ligand name: Wnt-C59
type: SyntheticOrganicLigand

GNF-1331
in ch i key: JIUFLMSAFMXEEC-UHFFFAOYSA-N
in ch i: InChI=1S/C20H20N6O2S2/c1-3-10-26-18(13-6-8-21-9-7-13)24-25-20(26)29-12-17(27)23-19-22-15-5-4-14(28-2)11-16(15)30-19/h4-9,11H,3,10,12H2,1-2H3,(H,22,23,27)
comment: GNF-1331 is an experimental inhibitor of the membrane bound O-acyl transferase porcupine (PORCN) <Reference id=40108/>.
iupac name: N-(6-methoxy-1,3-benzothiazol-2-yl)-2-[(4-propyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)sulfanyl]acetamide
xref: CHEMBL4540197
synonym: GNF1331
approved: f
ligand name: GNF-1331
type: SyntheticOrganicLigand

cefmenoxime
in ch i key: HJJDBAOLQAWBMH-YCRCPZNHSA-N
in ch i: InChI=1S/C16H17N9O5S3/c1-24-16(20-22-23-24)33-4-6-3-31-13-9(12(27)25(13)10(6)14(28)29)19-11(26)8(21-30-2)7-5-32-15(17)18-7/h5,9,13H,3-4H2,1-2H3,(H2,17,18)(H,19,26)(H,28,29)/b21-8-/t9-,13-/m1/s1
comment: Cefmenoxime is a semisynthetic, third generation cephalosporin and belongs to the β-lactam class of antibacterial compounds <Reference id=43754/>. It has broad-spectrum activity against both Gram-positive and Gram-negative bacteria and is resistant to hydrolysis by β-lactamases.
iupac name: (6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
xref: CHEMBL1201224
synonym: SCE-1365
synonym: A-50912
synonym: Cefmax®
synonym: Bestron®
synonym: SCE 1365
synonym: SCE1365
synonym: Abbott 50192
synonym: Abbott-50192
synonym: Abbott50192
approved: t
ligand name: cefmenoxime
type: SyntheticOrganicLigand

cefdinir
isomeric SMILES: C=CC1=C(N2[C@@H]([C@@H](C2=O)NC(=O)/C(=N/O)/c2csc(n2)N)SC1)C(=O)O
in ch i key: RTXOFQZKPXMALH-GHXIOONMSA-N
in ch i: InChI=1S/C14H13N5O5S2/c1-2-5-3-25-12-8(11(21)19(12)9(5)13(22)23)17-10(20)7(18-24)6-4-26-14(15)16-6/h2,4,8,12,24H,1,3H2,(H2,15,16)(H,17,20)(H,22,23)/b18-7-/t8-,12-/m1/s1
comment: Cefdinir is a semisynthetic, third generation cephalosporin and belongs to the β-lactam class of antibacterial compounds <Reference id=43752/>. It has broad-spectrum activity against both Gram-positive and Gram-negative aerobic bacteria and is stable to hydrolysis by many common β-lactamases.
iupac name: (6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-hydroxyiminoacetyl]amino]-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
xref: CHEMBL927
synonym: Omnicef®
synonym: FK 482
synonym: FK482
synonym: FK-482
approved: t
ligand name: cefdinir
type: SyntheticOrganicLigand

ceftibuten
isomeric SMILES: C1C=C(N2[C@H](S1)[C@@H](C2=O)NC(=O)/C(=C/CC(=O)O)/c1csc(n1)N)C(=O)O
in ch i key: UNJFKXSSGBWRBZ-BJCIPQKHSA-N
in ch i: InChI=1S/C15H14N4O6S2/c16-15-17-7(5-27-15)6(1-2-9(20)21)11(22)18-10-12(23)19-8(14(24)25)3-4-26-13(10)19/h1,3,5,10,13H,2,4H2,(H2,16,17)(H,18,22)(H,20,21)(H,24,25)/b6-1-/t10-,13-/m1/s1
comment: Ceftibuten is a semisynthetic, third generation cephalosporin and belongs to the β-lactam class of antibacterial compounds <Reference id=43763/>.
iupac name: (6R,7R)-7-[[(Z)-2-(2-amino-1,3-thiazol-4-yl)-4-carboxybut-2-enoyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
xref: CHEMBL1605
synonym: 7432-S
synonym: SCH 39720
synonym: SCH-39720
synonym: Cedax®
synonym: SCH39720
synonym: 7432 S
approved: t
ligand name: ceftibuten
type: SyntheticOrganicLigand

Compound 14a [WO2021155612A1]
in ch i key: PDKYBFRBTVUAEM-BJKOFHAPSA-N
in ch i: InChI=1S/C29H38N4O3/c1-5-29(6-2)18-26(34)33(28(30)32-29)24(16-19(3)4)20-10-9-11-21(17-20)27(35)31-23-14-15-36-25-13-8-7-12-22(23)25/h7-13,17,19,23-24H,5-6,14-16,18H2,1-4H3,(H2,30,32)(H,31,35)/t23-,24+/m0/s1
comment: Compound 14a is from a series of antimalarial analogues claimed in patent WO2021155612A1 <Reference id=43557/>.
approved: f
ligand name: Compound 14a [WO2021155612A1]
type: SyntheticOrganicLigand

cefpiramide
in ch i key: PWAUCHMQEXVFJR-PMAPCBKXSA-N
in ch i: InChI=1S/C25H24N8O7S2/c1-11-7-16(35)15(8-26-11)20(36)27-17(12-3-5-14(34)6-4-12)21(37)28-18-22(38)33-19(24(39)40)13(9-41-23(18)33)10-42-25-29-30-31-32(25)2/h3-8,17-18,23,34H,9-10H2,1-2H3,(H,26,35)(H,27,36)(H,28,37)(H,39,40)/t17-,18-,23-/m1/s1
comment: Cefpiramide is a semisynthetic, third generation cephalosporin and belongs to the β-lactam class of antibacterial compounds.
iupac name: (6R,7R)-7-[[(2R)-2-(4-hydroxyphenyl)-2-[(6-methyl-4-oxo-1H-pyridine-3-carbonyl)amino]acetyl]amino]-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
xref: CHEMBL1201204
synonym: SM-1652
synonym: SM 1652
synonym: WY-44635
synonym: WY 44635
approved: t
ligand name: cefpiramide
type: SyntheticOrganicLigand

latamoxef
in ch i key: JWCSIUVGFCSJCK-CAVRMKNVSA-N
in ch i: InChI=1S/C20H20N6O9S/c1-25-19(22-23-24-25)36-8-10-7-35-18-20(34-2,17(33)26(18)13(10)16(31)32)21-14(28)12(15(29)30)9-3-5-11(27)6-4-9/h3-6,12,18,27H,7-8H2,1-2H3,(H,21,28)(H,29,30)(H,31,32)/t12?,18-,20+/m1/s1
comment: Latamoxef is an oxacephem molecule developed by the Shionogi Research Laboratories (Osaka, Japan) <Reference id=43765/>. It belongs to the β-lactam class of antibacterial compounds.
iupac name: (6R,7R)-7-[[2-carboxy-2-(4-hydroxyphenyl)acetyl]amino]-7-methoxy-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-oxa-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
xref: CHEMBL74632
synonym: moxalactam
synonym: 6059-S
synonym: 6059 S
synonym: 6059S
synonym: LY127935
synonym: LY 127935
synonym: LY-127935
synonym: S 6059
synonym: S-6059
synonym: S6059
synonym: Lilly 127935
synonym: Moxam®
approved: t
ligand name: latamoxef
type: SyntheticOrganicLigand

compound A34 [PMID: 35635004]
in ch i key: VDIDNMGZRIMBKL-WOJBJXKFSA-N
comment: Compound A34 was reported as a selective FGFR4 inhibitor, with in vitro and in vivo anti-cancer activities <Reference id=43744/>. In vitro A34 inhibits both the wild type FGFR4 and the FGFR4V550L mutant (IC50s 5.4 nM and 98.2 nM respectively).
iupac name: N-[5-[3-(2,6-dichloro-3,5-dimethoxyphenyl)-1-ethyl-2-oxo-1,6-naphthyridin-7-yl]-4-methoxy-2-[(1R,4R)-2-oxa-5-azabicyclo[2.2.1]heptan-5-yl]phenyl]but-2-ynamide
approved: f
ligand name: compound A34 [PMID: 35635004]
type: SyntheticOrganicLigand

compound 47 [PMID: 35640059]
in ch i key: WXDKVCQSVUOFSK-UHFFFAOYSA-N
in ch i: InChI=1S/C23H20FNO4S/c24-17-7-3-14(4-8-17)11-19-21(18-9-10-29-13-20(18)30-19)22(26)25-12-15-1-5-16(6-2-15)23(27)28/h1-8H,9-13H2,(H,25,26)(H,27,28)
comment: Compound 47 is a selective prostaglandin E receptor 4 (EP4 receptor) antagonist <Reference id=43743/>, that was designed to counter the immunosuppressive effect of EP4/PGE2 signalling in the tumour microenvironment.
iupac name: 4-[[[2-[(4-fluorophenyl)methyl]-5,7-dihydro-4H-thieno[2,3-c]pyran-3-carbonyl]amino]methyl]benzoic acid
approved: f
ligand name: compound 47 [PMID: 35640059]
type: SyntheticOrganicLigand

compound 10c [Dampalla et al., 2022]
in ch i key: DXHKTWBJEAVWSD-QUJKESNLSA-N
comment: Compound 10c is one of the most potent coronavirus Mpro (3CLpro) inhibitors described by Dampalla et al. (2022) <Reference id=43742/>. It inhibits Mpros from MERS-CoV and SARS-CoV-2 in vitro and has low cellular toxicity (CC50 >100 μM). Compound 10c's structure contains a spirocyclic component and we show the molecule without the sodium adduct.
iupac name: (1R,2S)-1-hydroxy-2-[[(2S)-4-methyl-2-[(7-methylsulfonyl-7-azaspiro[3.5]nonan-2-yl)oxycarbonylamino]pentanoyl]amino]-3-[(3S)-2-oxopyrrolidin-3-yl]propane-1-sulfonic acid
approved: f
ligand name: compound 10c [Dampalla et al., 2022]
type: SyntheticOrganicLigand

rifabutin
in ch i key: ZWBTYMGEBZUQTK-PVLSIAFMSA-N
in ch i: InChI=1S/C46H62N4O11/c1-22(2)21-50-18-16-46(17-19-50)48-34-31-32-39(54)28(8)42-33(31)43(56)45(10,61-42)59-20-15-30(58-11)25(5)41(60-29(9)51)27(7)38(53)26(6)37(52)23(3)13-12-14-24(4)44(57)47-36(40(32)55)35(34)49-46/h12-15,20,22-23,25-27,30,37-38,41,48,52-55H,16-19,21H2,1-11H3/b13-12+,20-15+,24-14-,47-36?/t23-,25+,26+,27+,30-,37-,38+,41+,45-/m0/s1
comment: Rifabutin is a derivative of rifamycin S and belongs to the ansamycin group of antibacterial compounds <Reference id=43779/>. It is on the World Health Organization's Model List of Essential Medicines (link provided in the Classification table, under the Summary tab below) for use as an oral antituberculosis medication.
iupac name: [(7S,9E,11S,12R,13S,14R,15R,16R,17S,18S,19E,21Z)-2,15,17,32-tetrahydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-1'-(2-methylpropyl)-6,23-dioxospiro[8,33-dioxa-24,27,29-triazapentacyclo[23.6.1.14,7.05,31.026,30]tritriaconta-1(32),2,4,9,19,21,24,26,30-nonaene-28,4'-piperidine]-13-yl] acetate
xref: CHEMBL444633
synonym: LM 427
synonym: Mycobutin®
synonym: LM-427
synonym: LM427
synonym: Rifabutine
approved: t
ligand name: rifabutin
type: SyntheticOrganicLigand

rifapentine
in ch i key: WDZCUPBHRAEYDL-GZAUEHORSA-N
in ch i: InChI=1S/C47H64N4O12/c1-24-13-12-14-25(2)46(59)49-37-32(23-48-51-20-18-50(19-21-51)31-15-10-11-16-31)41(56)34-35(42(37)57)40(55)29(6)44-36(34)45(58)47(8,63-44)61-22-17-33(60-9)26(3)43(62-30(7)52)28(5)39(54)27(4)38(24)53/h12-14,17,22-24,26-28,31,33,38-39,43,53-57H,10-11,15-16,18-21H2,1-9H3,(H,49,59)/b13-12+,22-17+,25-14-,48-23+/t24-,26+,27+,28+,33-,38-,39+,43+,47-/m0/s1
comment: Rifapentine is a semisynthetic derivative of rifamycin and belongs to the ansamycin group of antibacterial compounds <Reference id=43777/>. Rifapentine is on the World Health Organization's Model List of Essential Medicines (link provided in the Classification table, under the Summary tab below) for use as an oral antituberculosis medication.
iupac name: [(7S,9E,11S,12R,13S,14R,15R,16R,17S,18S,19E,21Z)-26-[(E)-(4-cyclopentylpiperazin-1-yl)iminomethyl]-2,15,17,27,29-pentahydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-6,23-dioxo-8,30-dioxa-24-azatetracyclo[23.3.1.14,7.05,28]triaconta-1(29),2,4,9,19,21,25,27-octaen-13-yl] acetate
xref: CHEMBL1660
synonym: Priftin®
synonym: DL 473
synonym: DL-473
synonym: DL473
synonym: MDL 473
synonym: MDL-473
synonym: MDL473
approved: t
ligand name: rifapentine
type: SyntheticOrganicLigand

rifaximin
in ch i key: NZCRJKRKKOLAOJ-XRCRFVBUSA-N
in ch i: InChI=1S/C43H51N3O11/c1-19-14-16-46-28(18-19)44-32-29-30-37(50)25(7)40-31(29)41(52)43(9,57-40)55-17-15-27(54-10)22(4)39(56-26(8)47)24(6)36(49)23(5)35(48)20(2)12-11-13-21(3)42(53)45-33(34(32)46)38(30)51/h11-18,20,22-24,27,35-36,39,48-51H,1-10H3,(H,45,53)/b12-11+,17-15+,21-13-/t20-,22+,23+,24+,27-,35-,36+,39+,43-/m0/s1
comment: Rifaximin is a semisynthetic derivative of rifamycin and belongs to the ansamycin group of antibacterial compounds <Reference id=43775/>. It has broad spectrum activity against Gram-positive and Gram-negative bacteria.
iupac name: [(7S,9E,11S,12R,13S,14R,15R,16R,17S,18S,19E,21Z)-2,15,17,36-tetrahydroxy-11-methoxy-3,7,12,14,16,18,22,30-octamethyl-6,23-dioxo-8,37-dioxa-24,27,33-triazahexacyclo[23.10.1.14,7.05,35.026,34.027,32]heptatriaconta-1(35),2,4,9,19,21,25(36),26(34),28,30,32-undecaen-13-yl] acetate
xref: CHEMBL1617
synonym: L/105
synonym: L-105
synonym: Rifamycin L 105
synonym: Xifaxan®
approved: t
ligand name: rifaximin
type: SyntheticOrganicLigand

SNX281
in ch i key: CLGJCTXUWJLYHO-UHFFFAOYSA-N
in ch i: InChI=1S/C20H20ClNO3S/c1-20(2,3)11-5-6-12-15(9-11)22(10-16(23)24)17-13(18(12)25)7-8-14(21)19(17)26-4/h5-9H,10H2,1-4H3,(H,23,24)
comment: SNX281 is a systemically active stimulator of interferon genes (STING) agonist, that was developed to induce anti-tumour immunity <Reference id=43725/>. SNX281 is competitive with the endogenous cyclic dinucleotide STING agonist <Ligand id=9207/>. Analysis reveals that SNX281 self-dimerises to generate a structure that is large enough to occupy STING's cyclic dinucleotide binding site, which switches the protein to its active state conformation.
iupac name: 2-(6-tert-butyl-3-chloro-4-methylsulfanyl-9-oxoacridin-10-yl)acetic acid
approved: f
ligand name: SNX281
type: SyntheticOrganicLigand

tuspetinib
in ch i key: FZLSDZZNPXXBBB-KDURUIRLSA-N
in ch i: InChI=1S/C29H33ClN6/c1-17-4-7-24-25(12-31-27(24)8-17)28-26(30)13-32-29(35-28)34-23-10-20(9-22(11-23)21-5-6-21)16-36-14-18(2)33-19(3)15-36/h4,7-13,18-19,21,31,33H,5-6,14-16H2,1-3H3,(H,32,34,35)/t18-,19+
comment: HM43239 is an orally active, clinical stage compound that inhibits a number of kinases that are active in myeloid malignancies, including FLT3, SYK, mutant forms of cKIT, JAK1/2, and other kinases <Reference id=43724/>. It is intended as a treament for patients with relapsed/refractory acute myeloid leukemia (AML). We matched its chemical structure to the INN 'tuspetinib' that was released in the WHO's proposed INN list 127 (21 July 2022).
iupac name: 5-chloro-N-[3-cyclopropyl-5-[[(3R,5S)-3,5-dimethylpiperazin-1-yl]methyl]phenyl]-4-(6-methyl-1H-indol-3-yl)pyrimidin-2-amine
synonym: HM-43239
synonym: example 8 [US10870639B2]
synonym: HM43239
approved: f
ligand name: tuspetinib
type: SyntheticOrganicLigand

oxalate
canonical SMILES: [O-]C(=O)C(=O)[O-]
isomeric SMILES: [O-]C(=O)C(=O)[O-]
in ch i key: MUBZPKHOEPUJKR-UHFFFAOYSA-L
in ch i: InChI=1S/C2H2O4/c3-1(4)2(5)6/h(H,3,4)(H,5,6)/p-2
iupac name: oxalate
synonym: oxalate2-
approved: f
ligand name: oxalate
type: MetaboliteLigand

XL01126
in ch i key: XSOATTNBVDAEAR-QGHWPEOCSA-N
comment: XL01126 is a VHL-based PROTAC degrader targeting leucine rich repeat kinase 2 (LRRK2). The LRRK2 binding moeity of the compound is the brain-penetrant kinase inhibitor <Ligand id=9392/>. XL01126 is orally bioavailable and retains the ability of the parent kinase inhibitor to cross the blood-brain barrier. LRRK2 is an active therapeutic target for Parkinson's disease, since activating coding mutations in LRRK2 are associated with dominantly inherited Parkinson's disease <Reference id=43718/><Reference id=43719/><Reference id=43720/>. XL01126's development was led by Dundee University's Centre for Targeted Protein Degradation and the Research Institute for Medicines at the University of Lisbon. Initially disclosed in a ChemRxiv preprint <Reference id=43722/>. Cereblon-targeting LRRK2 PROTACs have been disclosed previously, but these were found to be inefficient target degraders <Reference id=43721/>.
approved: f
ligand name: XL01126
type: SyntheticOrganicLigand

tegoprazan
in ch i key: CLIQCDHNPDMGSL-HNNXBMFYSA-N
in ch i: InChI=1S/C20H19F2N3O3/c1-10-23-14-6-11(20(26)25(2)3)7-17(19(14)24-10)28-15-4-5-27-16-9-12(21)8-13(22)18(15)16/h6-9,15H,4-5H2,1-3H3,(H,23,24)/t15-/m0/s1
comment: Tegoprazan (CJ-12420) is an oral, fast-acting potassium-competitive acid blocker (P-CAB) <Reference id=43717/>. It reduces gastric acid secretion by inhibiting the H+/K+ transporter (ATP4A; a.k.a. the gastric proton pump) in the stomach lining.
iupac name: 7-[[(4S)-5,7-difluoro-3,4-dihydro-2H-chromen-4-yl]oxy]-N,N,2-trimethyl-3H-benzimidazole-5-carboxamide
xref: CHEMBL4297583
synonym: CJ-12420
synonym: CJ12420
synonym: K-CAB®
approved: t
ligand name: tegoprazan
type: SyntheticOrganicLigand

compound 24 [PMID: 35286090]
in ch i key: MZGYQJDGUVDYIK-UHFFFAOYSA-N
in ch i: InChI=1S/C28H38N4O5S2/c1-26(2,3)31-38(34,35)22-7-5-6-20(18-22)29-25(33)23-9-8-21(30-39(36,37)27(4)10-11-27)19-24(23)32-16-14-28(12-13-28)15-17-32/h5-9,18-19,30-31H,10-17H2,1-4H3,(H,29,33)
comment: This compound is reported as an inhibitor of kinesin family member 18A (KIF18A; Q8NI77) <Reference id=43709/>. Compound 24 binds at the interface of KIF18A and tubulin. KIF18A is a molecular target for the development of therapeutics for chromosomally unstable cancers. Inhibiting KIF18A function drives mitotic arrest and cell death. Compound 24 shares some structural similarity with the clinical stage KIF18A inhibitor <Ligand id=11949/>.
approved: f
ligand name: compound 24 [PMID: 35286090]
type: SyntheticOrganicLigand

DS69910557
in ch i key: JAOGFYSXDYNYSX-UHFFFAOYSA-N
comment: DS69910557 is a potent and selective human parathyroid hormone receptor 1 (hPTHR1) antagonist <Reference id=43708/>. PTHR1 antagonism is being investigated for the management of disease states in which mineral ion homeostasis and bone are perturbed, such as hyperparathyroidism, hypercalcemia of malignancy, and osteoporosis.
iupac name: 4-[[1-[4-(2,9-dichloro-5,5-dimethyl-6-oxo-pyrido[2,3-d][1]benzazepin-7-yl)phenyl]-3-fluoro-azetidin-3-yl]methylamino]cyclohexanecarboxylic acid
synonym: Compound 19e [PMID: 35487102]
synonym: DS-69910557
approved: f
ligand name: DS69910557
type: SyntheticOrganicLigand

lenrispodun
in ch i key: BBIPVJCGIASXJB-PKTZIBPZSA-N
in ch i: InChI=1S/C29H26FN7O/c1-35-28(38)25-26(31-20-7-3-2-4-8-20)36(34-27(25)37-23-11-5-10-22(23)33-29(35)37)17-18-13-15-19(16-14-18)21-9-6-12-24(30)32-21/h2-4,6-9,12-16,22-23,31H,5,10-11,17H2,1H3/t22-,23+/m1/s1
comment: Lenrispodun (ITI-214) is a potent (picomolar) and selective PDE1 inhibitor <Reference id=43706/>. It is CNS-active and orally bioavailable, and demonstrates selectivity against other PDE family enzymes. Lenrispodun was developed as a novel mechanism for the treatment of cognitive impairment/dysfunction that is associated with neurodegenerative and neuropsychiatric diseases <Reference id=43707/>.
xref: CHEMBL3769414
synonym: ITI-214
synonym: ITI214
synonym: compound 3 [PMID: 26789933]
approved: f
ligand name: lenrispodun
type: SyntheticOrganicLigand

ABBV-318
in ch i key: FWLFRXVPNVBXGR-CQSZACIVSA-N
in ch i: InChI=1S/C20H15F4N3O2/c21-14-7-8-27(11-14)19(28)17-4-1-12-9-15(3-5-16(12)26-17)29-18-6-2-13(10-25-18)20(22,23)24/h1-6,9-10,14H,7-8,11H2/t14-/m1/s1
comment: ABBV-318 is an orally bioavailable, CNS-penetrant blocker of voltage-gated sodium channels Nav1.7/Nav1.8 <Reference id=43705/>. Both Nav1.7 and Nav1.8 are active therapeutic targets for the development of new anti-pain medications.
iupac name: [(3R)-3-fluoropyrrolidin-1-yl]-[6-[5-(trifluoromethyl)pyridin-2-yl]oxyquinolin-2-yl]methanone
xref: CHEMBL3970885
synonym: ABBV318
synonym: compound 73 [PMID: 35436748]
approved: f
ligand name: ABBV-318
type: SyntheticOrganicLigand

JBJ-09-063
in ch i key: SYTVDTWRIZNVEW-UHFFFAOYSA-N
in ch i: InChI=1S/C31H29FN4O3S/c1-35-13-10-21(11-14-35)19-2-4-20(5-3-19)22-6-7-23-18-36(30(39)25(23)16-22)28(26-17-24(32)8-9-27(26)37)29(38)34-31-33-12-15-40-31/h2-9,12,15-17,21,28,37H,10-11,13-14,18H2,1H3,(H,33,34,38)
comment: JBJ-09-063 is a negative allosteric modulator (inhibitor) of mutant-epidermal growth factor receptor (EGFR) in tumours <Reference id=43704/>. It was designed to provide efficacy in in EGFR-mutant cancers with resistance to existing ATP-competitive receptor tyrosine kinase inhibitors.
approved: f
ligand name: JBJ-09-063
type: SyntheticOrganicLigand

MS40
in ch i key: STBAQMSNPQNEBZ-UHFFFAOYSA-N
comment: MS40 is a cereblon (CRBN)-based proteolysis targeting chimera (PROTAC) degrader of the onco-target WD repeat domain 5 (WDR5) <Reference id=43702/>. WDR5 is an integral component of the MLL/KMT2A lysine methyltransferase protein complex. The WDR5-binding component of MS40 is the selective inhibitor <Ligand id=8231/>, and the CRBN-targeting moiety is the immunomodulatory drug <Ligand id=7348/>. MS40 promotes degradation of WDR5 and the pomalidomide transcription factor neo-substrates IKZF1 and IKZF3.
iupac name: N-[5-[3-[[4-[2-[8-[[2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-4-yl]amino]octanoylamino]ethyl]piperazin-1-yl]methyl]phenyl]-2-(4-methylpiperazin-1-yl)phenyl]-6-oxo-4-(trifluoromethyl)-1H-pyridine-3-carboxamide
approved: f
ligand name: MS40
type: SyntheticOrganicLigand

compound 41 [PMID: 35436124]
in ch i key: FFUQRXFVTVBZMZ-SANMLTNESA-N
in ch i: InChI=1S/C29H29F3N6O/c1-3-37-16-24(27(35-37)29(30,31)32)22-13-19(15-36-11-9-33-17-36)14-23-21(22)7-10-38(28(23)39)26(20-4-5-20)25-12-18(2)6-8-34-25/h6,8-9,11-14,16-17,20,26H,3-5,7,10,15H2,1-2H3/t26-/m0/s1
comment: Compound 41 is a small molecule, oral WD repeat domain 5 (WDR5) inhibitor <Reference id=43696/>. It interacts with the WDR5 interaction motif (WIN)-site which is an important binding interface for the formation of WDR5-based protein complexes. Compound 41 was developed to disrupt WDR5's participation in chromatin regulatory complexes and epigenetic processes in cancers.
iupac name: 2-[(S)-cyclopropyl-(4-methylpyridin-2-yl)methyl]-5-[1-ethyl-3-(trifluoromethyl)pyrazol-4-yl]-7-(imidazol-1-ylmethyl)-3,4-dihydroisoquinolin-1-one
approved: f
ligand name: compound 41 [PMID: 35436124]
type: SyntheticOrganicLigand

terevalefim
canonical SMILES: c1csc(c1)/C=C/c1[nH]ncc1
isomeric SMILES: c1csc(c1)/C=C/c1ccn[nH]1
in ch i key: FOHWAQGURRYJFK-ONEGZZNKSA-N
in ch i: InChI=1S/C9H8N2S/c1-2-9(12-7-1)4-3-8-5-6-10-11-8/h1-7H,(H,10,11)/b4-3+
comment: Terevalefim (ANG-3777) is a clinical stage small molecule hepatocyte growth factor (HGF) mimetic. HGF as a pleiotropic factor with roles in organ regeneration <Reference id=43692/><Reference id=43693/><Reference id=43694/>. Like HGF, terevalefim activates the HGF/c-MET pathway, to promote tissue and organ repair and function. Terevalefim was developed as a first-in-class therapeutic to target acute organ injury.
iupac name: 5-[(E)-2-thiophen-2-ylethenyl]-1H-pyrazole
xref: CHEMBL4650326
synonym: Refanalin
synonym: ANG-3777
synonym: ANG3777
approved: f
ligand name: terevalefim
type: SyntheticOrganicLigand

riamilovir
canonical SMILES: CSc1[nH]n2c(n1)nnc(c2=O)[N+](=O)[O-]
isomeric SMILES: CSc1nc2nnc(c(=O)n2[nH]1)[N+](=O)[O-]
in ch i key: IDVQGNMSSHPZSJ-UHFFFAOYSA-N
in ch i: InChI=1S/C5H4N6O3S/c1-15-5-6-4-8-7-2(11(13)14)3(12)10(4)9-5/h1H3,(H,6,8,9)
comment: Riamilovir is a synthetic guanine derivative that acts as a broad-spectrum antiviral agent. It disrupts viral transcription and replication, with antiviral activity against a range of RNA viruses. The exact molecular target has not been reported, although molecular docking studies suggest an interaction of riamilovir with SARS-CoV-2 Mpro (3CL protease) <Reference id=43690/>. Consequently, riamilovir has been advanced into clinical evaluation for potential anti-SARS-CoV-2 activity.
iupac name: 7-methylsulfanyl-3-nitro-6H-[1,2,4]triazolo[5,1-c][1,2,4]triazin-4-one
xref: CHEMBL1618116
synonym: Triazavirin®
synonym: TZV
approved: f
ligand name: riamilovir
type: SyntheticOrganicLigand

AZD4625
in ch i key: KYVBBJIEKCCZTM-OLZOCXBDSA-N
comment: AZD4625 is a covalent, negative allosteric modulator of the mutant and oncogenic GTPase KRASG12C <Reference id=43591/>.
synonym: compound 21 [PMID: 35471939]
synonym: AZD-4625
synonym: AZD 4625
approved: f
ligand name: AZD4625
type: SyntheticOrganicLigand

HR1405-01
in ch i key: SHAHPWSYJFYMRX-GDLCADMTSA-N
in ch i: InChI=1S/C15H20O3/c1-10(15(17)18)12-7-5-11(6-8-12)9-13-3-2-4-14(13)16/h5-8,10,13-14,16H,2-4,9H2,1H3,(H,17,18)/t10-,13+,14-/m0/s1
comment: HR1405-01 is a tromethamine salt of the active loxoprofenol (an NSAID) metabolite, loxoprofenol-SRS <Reference id=43579/><Reference id=43580/>. It was developed for potential anti-inflammatory and analgesic activities, and is formulated for intravenous administration.
iupac name: (S)-2-(4-(((1R,2S)-2-Hydroxycyclopentyl)methyl)phenyl)propanoic acid
xref: CHEMBL441414
synonym: loxoprofen trans-alcohol
synonym: compound 5a [PMID: 14980665]
approved: f
ligand name: HR1405-01
type: SyntheticOrganicLigand

uproleselan
in ch i key: LYSYOXNOOPBOSC-NGSKMYNLSA-N
in ch i: InChI=1S/C60H109N3O27/c1-5-44-38-45(39-46(55(44)90-60-54(70)53(69)51(67)41(2)86-60)88-59-50(63-42(3)65)56(52(68)48(40-64)89-59)87-47(58(72)73)37-43-9-7-6-8-10-43)57(71)62-13-12-61-49(66)11-14-75-17-18-77-21-22-79-25-26-81-29-30-83-33-34-85-36-35-84-32-31-82-28-27-80-24-23-78-20-19-76-16-15-74-4/h41,43-48,50-56,59-60,64,67-70H,5-40H2,1-4H3,(H,61,66)(H,62,71)(H,63,65)(H,72,73)/t41-,44-,45+,46+,47-,48+,50+,51+,52-,53+,54-,55+,56+,59+,60-/m0/s1
comment: Uproleselan (GMI-1271) is a selective, glycomimetic, selectin E antagonist <Reference id=43682/>. It prevents leukocyte adhesion to endothelial cells. Uproleselan disrupts leukocyte-mediated endothelial damage <Reference id=43683/>, a mechanism that has been examined for potential to combat venous thrombosis <Reference id=43684/><Reference id=43685/>. It is also under investigation for use in cancer as selectin E is involved in cancer cell trafficking <Reference id=43686/>. In the tumour microenvironment uproleselan disrupts extravasation and adhesion which are crucial components that contribute to metastasis. COVID-19: Selectin E is a biomarker for acute respiratory distress syndrome (ARDS), that has pro-inflammatory actions that enhance cytokine release and promote continued influx of neutrophils. This existing evidence had led to inclusion of uproleselan in a clinical trial that is designed to determine if antagonising selectin E can aid recovery in patients with severe COVID-19 pneumonia/ARDS.
xref: CHEMBL3989971
synonym: GMI-1271
synonym: GMI1271
synonym: ABI-701
synonym: ABI701
approved: f
ligand name: uproleselan
type: SyntheticOrganicLigand

edaravone
canonical SMILES: O=C1CC(=NN1c1ccccc1)C
isomeric SMILES: CC1=NN(C(=O)C1)c1ccccc1
in ch i key: QELUYTUMUWHWMC-UHFFFAOYSA-N
in ch i: InChI=1S/C10H10N2O/c1-8-7-10(13)12(11-8)9-5-3-2-4-6-9/h2-6H,7H2,1H3
comment: Edaravone (MCI-186) is a free radical scavenger <Reference id=43666/>. It is used clinically for its neuroprotective action.
iupac name: 5-methyl-2-phenyl-4H-pyrazol-3-one
synonym: MCI-186
synonym: MCI186
synonym: Radicava®
synonym: Radicut®
approved: f
ligand name: edaravone
type: SyntheticOrganicLigand

VV116
in ch i key: RVSSLHFYCSUAHY-QXMJNOOVSA-N
in ch i: InChI=1S/C24H31N5O7/c1-12(2)21(30)33-9-16-18(34-22(31)13(3)4)19(35-23(32)14(5)6)24(10-25,36-16)17-8-7-15-20(26)27-11-28-29(15)17/h7-8,11-14,16,18-19H,9H2,1-6H3,(H2,26,27,28)/t16-,18-,19-,24+/m1/s1/i7D
comment: VV116 is an orally available, deuterated <Ligand id=10715/> analogue <Reference id=43656/>. It is a tri-isobutyrate ester prodrug (formulated as the hydrobromide salt) that is converted to an active nucleoside triphosphate (116-NTP) that acts as a viral RNA-dependent RNA polymerase (RdRP) inhibitor. VV116 was developed for antiviral activity against SARS-CoV-2. WE drew the chemical structure as represented in Xie et al. (2021) <Reference id=43656/>.
synonym: JT001
synonym: VV-116
synonym: X6 hydrobromide [PMID: 34584244]
approved: f
ligand name: VV116
type: SyntheticOrganicLigand

phenoxybenzamine
canonical SMILES: ClCCN(C(COc1ccccc1)C)Cc1ccccc1
isomeric SMILES: ClCCN(C(COc1ccccc1)C)Cc1ccccc1
in ch i key: QZVCTJOXCFMACW-UHFFFAOYSA-N
in ch i: InChI=1S/C18H22ClNO/c1-16(15-21-18-10-6-3-7-11-18)20(13-12-19)14-17-8-4-2-5-9-17/h2-11,16H,12-15H2,1H3
comment: Phenoxybenzamine is a non-selective, irreversible alpha blocker (α-adrenoceptor antagonist).
iupac name: benzyl(2-chloroethyl)(1-phenoxypropan-2-yl)amine
xref: CHEMBL753
synonym: phenoxybenzamine hydrochloride
synonym: Dibenzyline®
approved: t
ligand name: phenoxybenzamine
type: SyntheticOrganicLigand

pruxelutamide
in ch i key: KCBJGVDOSBKVKP-UHFFFAOYSA-N
comment: Pruxelutamide (a.k.a. proxalutamide, GT0918) is an androgen receptor (AR) antagonist <Reference id=43644/> that was originally designed as an anti-prostate cancer drug <Reference id=43640/><Reference id=43638/>. It binds to the ligand-binding domain of AR more potently than <Ligand id=6812/> <Reference id=43644/>. Antiviral activity against SARS-CoV-2 has been reported <Reference id=43639/> and clinical trials have evaluated efficacy in COVID-19 patients <Reference id=43641/><Reference id=43643/> (however note the publisher's 'Expression of concern' regarding the McCoy et al. study <Reference id=43642/>).
xref: CHEMBL4594417
synonym: GT0918
synonym: GT-0918
synonym: proxalutamide
approved: f
ligand name: pruxelutamide
type: SyntheticOrganicLigand

ezurpimtrostat
in ch i key: QVXSJSXAVQJXOV-UHFFFAOYSA-N
in ch i: InChI=1S/C25H31ClN4/c1-25(2,3)29-20-12-14-30(15-13-20)23-16-24(28-22-7-5-4-6-21(22)23)27-17-18-8-10-19(26)11-9-18/h4-11,16,20,29H,12-15,17H2,1-3H3,(H,27,28)
comment: Ezurpimtrostat (GNS561) is a small molecule inhibitor of palmitoyl-protein thioesterase 1 (PPT1). It induces lysosomal dysregulation which leads to inhibition of late-stage autophagy and cell death. Antitumour and antiviral activities have been demonstrated in vitro and in vivo <Reference id=43634/><Reference id=43633/><Reference id=43635/><Reference id=43636/><Reference id=43637/>.
iupac name: 4-[4-(tert-butylamino)piperidin-1-yl]-N-[(4-chlorophenyl)methyl]quinolin-2-amine
synonym: GNS561
synonym: GNS-561
approved: f
ligand name: ezurpimtrostat
type: SyntheticOrganicLigand

EP-7041
in ch i key: NYPSZHLKEMYZKK-XFJVYGCCSA-N
in ch i: InChI=1S/C19H26N4O4/c1-11(13-5-3-2-4-6-13)22-19(27)23-16(18(25)26)14(17(23)24)9-12-7-8-21-15(20)10-12/h7-8,10-11,13-14,16H,2-6,9H2,1H3,(H2,20,21)(H,22,27)(H,25,26)/t11-,14-,16+/m1/s1
comment: EP-7041 is a parenteral, selective small-molecule activated factor XIa inhibitor <Reference id=43628/>. It has a very short half-life compared with other FXIa-targeted therapeutics such as the anti-FXIa mAb <Ligand id=11366/>, and therefore exerts a short-lived antithrombotic effect.
iupac name: (2S,3R)-3-[(2-aminopyridin-4-yl)methyl]-1-[[(1R)-1-cyclohexylethyl]carbamoyl]-4-oxoazetidine-2-carboxylic acid
synonym: EP7041
approved: f
ligand name: EP-7041
type: SyntheticOrganicLigand

compound 15 [PMID: 35450354]
in ch i key: PNGWZDXPZBZBRC-NHCUHLMSSA-N
in ch i: InChI=1S/C23H28FN5/c1-13-8-16(9-14(2)25-13)18-11-22-19(10-17(18)15-4-5-15)23(28-27-22)26-21-6-7-29(3)12-20(21)24/h8-11,15,20-21H,4-7,12H2,1-3H3,(H2,26,27,28)/t20-,21-/m1/s1
comment: This compound is a dual Toll-like receptor 7/8 antagonist <Reference id=43625/>. It produces predicted pharmacodynamic effect (inhibition of TLR7-dependent IFNα release) in vivo following oral administration.
approved: f
ligand name: compound 15 [PMID: 35450354]
type: SyntheticOrganicLigand

danicopan
in ch i key: PIBARDGJJAGJAJ-NQIIRXRSSA-N
comment: Danicopan (ACH-4471) is an oral, direct inhibitor of the protease activity of complement factor D <Reference id=43623/><Reference id=43622/><Reference id=43619/>, which is a component of the alternative complement pathway. It was originally developed for potential to control complement-mediated intravascular hemolysis and prevent C3-mediated extravascular hemolysis in patients with paroxysmal nocturnal hemoglobinuria <Reference id=43620/>. COVID-19: Danicoplan is being included in the ACTIV-5 platform trial NCT04988035 that is designed to identify promising agents as potential COVID-19 therapeutics that are suitable for progression to more definitive studies. It is initially being tested as a monotherapy and in combination with <Ligand id=10715/> in hospitalised COVID-19 patients.
xref: CHEMBL4250860
synonym: ACH-4471
synonym: ACH4471
approved: f
ligand name: danicopan
type: SyntheticOrganicLigand

BIO101
in ch i key: NKDFYOWSKOHCCO-YPVLXUMRSA-N
in ch i: InChI=1S/C27H44O7/c1-23(2,32)9-8-22(31)26(5,33)21-7-11-27(34)16-12-18(28)17-13-19(29)20(30)14-24(17,3)15(16)6-10-25(21,27)4/h12,15,17,19-22,29-34H,6-11,13-14H2,1-5H3/t15-,17-,19+,20-,21-,22+,24+,25+,26+,27+/m0/s1
comment: BIO101 is pharmaceutical grade 20-hydroxyecdysone, the latter being a natural product found in the Asparagus filicinus fern, the trematode Trichobilharzia ocellata, and other organisms. Its activity as a non-peptidic activator of the class A orphan GPCR MAS1 has been proposed to offer potential clinical utility to counteract dysregulation of the renin-angiotensin system (RAS) in patients with COVID-19 respiratory failure <Reference id=43618/><Reference id=43617/>. Given the role of ACE2 in the RAS, and the disturbance of ACE2 function that likely ensues when SARS-CoV-2 spike protein binds to ACE2, it is feasible that the RAS will be dysregulated in COVID-19, and that ameliorating this disruption through targeted pharmacological intervention might be of potential clinical benefit.
synonym: 20-Hydroxyecdysone
synonym: Crustecdysone
synonym: Ecdysterone
synonym: beta-Ecdysone
synonym: Sarconeos
approved: f
ligand name: BIO101
type: NaturalProductLigand

compound 27 [WO2019226977A1]
in ch i key: TVTJUIAKQFIXCE-HUKYDQBMSA-N
in ch i: InChI=1S/C13H14FN5O5/c1-2-3-18-7-9(16-12(15)17-10(7)22)19(13(18)23)11-8(21)6(14)5(4-20)24-11/h1,5-6,8,11,20-21H,3-4H2,(H3,15,16,17,22)/t5-,6-,8-,11-/m1/s1
comment: This compound is predicted to be the active version of the TLR7 agonist prodrug <Ligand id=11872/>. It is claimed as compound 27 in Primmune Therapeutics' patent WO2019226977A1 <Reference id=43588/>. TLR7 agonists are predicted to offer clinical benefit in patients with severe COVID-19 <Reference id=43589/>, since some loss-of-function variants in TLR7 are associated with increased COVID-19 disease severity (likely via blunted type I IFN production) <Reference id=43590/>. We can make a provisional link between compound 27 and the active TLR7 agonist PRX034.
iupac name: 2-amino-9-[(2R,3S,4S,5R)-4-fluoro-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-7-prop-2-ynyl-1H-purine-6,8-dione
approved: f
ligand name: compound 27 [WO2019226977A1]
type: SyntheticOrganicLigand

chlorprothixene
canonical SMILES: CN(CC/C=C/1/c2ccccc2Sc2c1cc(Cl)cc2)C
isomeric SMILES: CN(C)CC/C=C/1/c2ccccc2Sc2c1cc(cc2)Cl
in ch i key: WSPOMRSOLSGNFJ-AUWJEWJLSA-N
in ch i: InChI=1S/C18H18ClNS/c1-20(2)11-5-7-14-15-6-3-4-8-17(15)21-18-10-9-13(19)12-16(14)18/h3-4,6-10,12H,5,11H2,1-2H3/b14-7-
comment: Chlorprothixene can be classified as a (tricyclic) typical antipsychotic drug. The INN record stipulates the (Z) conformer. Mechanistically it acts at multiple GPCRs to mediate its neurological effects. Direct interactions with 5-HT2, dopamine D1, D2, D3, histamine H1, muscarinic and α1 adrenergic receptors have been demonstrated.
iupac name: (3Z)-3-(2-chlorothioxanthen-9-ylidene)-N,N-dimethylpropan-1-amine
xref: CHEMBL908
synonym: N-714
synonym: Ro-4-0403
synonym: Taractan®
synonym: Truxal®
approved: t
ligand name: chlorprothixene
type: SyntheticOrganicLigand

etavopivat
in ch i key: KZFFYEPYCVDOGE-LJQANCHMSA-N
in ch i: InChI=1S/C22H23N3O6S/c26-14-19(15-4-2-1-3-5-15)22(27)24-10-16-12-25(13-17(16)11-24)32(28,29)18-8-20-21(23-9-18)31-7-6-30-20/h1-5,8-9,19,26H,6-7,10-14H2/t19-/m1/s1
comment: Etavopivat (FT-4202) is an orally active, small molecule allosteric activator of the pyruvate kinase (PK) isoform that's found in erythrocytes (PK-R) <Reference id=43582/>. It activates the erythrocytic glycolytic pathway. Etavopivat is similar in function to <Ligand id=10473/>.
xref: CHEMBL4650332
synonym: FT-4202
synonym: FT4202
approved: f
ligand name: etavopivat
type: SyntheticOrganicLigand

guvacine
canonical SMILES: OC(=O)C1=CCCNC1
isomeric SMILES: OC(=O)C1=CCCNC1
in ch i key: QTDZOWFRBNTPQR-UHFFFAOYSA-N
in ch i: InChI=1S/C6H9NO2/c8-6(9)5-2-1-3-7-4-5/h2,7H,1,3-4H2,(H,8,9)
comment: A pyridine alkaloid found in the Areca nut.
iupac name: 1,2,5,6-tetrahydropyridine-3-carboxylic acid
xref: CHEMBL76768
approved: f
ligand name: guvacine
type: NaturalProductLigand

AMY-101
in ch i key: MUSGYEMSJUFFHT-UWABRSFTSA-N
comment: AMY-101 is a cyclic peptide analogue of <Ligand id=9218/> <Reference id=31215/><Reference id=43615/><Reference id=43616/>. Like compstatin it acts as an inhibitor of complement component 3 (C3), and as an immunomodulator.
xref: CHEMBL4297260
synonym: Compstatin analog CP40
synonym: AMY101
synonym: Compstatin 40
synonym: CP-40
synonym: peptide 14 [PMID: 22795972]
approved: f
ligand name: AMY-101
type: PeptideLigand

isuzinaxib
canonical SMILES: CCCc1c([nH]n(c1=O)c1ccccn1)c1ccccc1
isomeric SMILES: CCCc1c([nH]n(c1=O)c1ccccn1)c1ccccc1
in ch i key: GIWZEELPLKPYBA-UHFFFAOYSA-N
in ch i: InChI=1S/C17H17N3O/c1-2-8-14-16(13-9-4-3-5-10-13)19-20(17(14)21)15-11-6-7-12-18-15/h3-7,9-12,19H,2,8H2,1H3
comment: Isuzinaxib (APX-115) is a first-in-class pan-NADPH oxidase (NOX) inhibitor <Reference id=43605/>. We show the chemical structure for the free base, but it is generally delivered as the hydrochloride salt. Isuzinaxib was designed to reduce cellular oxidative stress and tissue injury caused by imbalanced reactive oxygen species (ROS) production in pathological condtions. NADPH oxidases (NOX1-5, DUOX1 and DUOX2) are the major sources of ROS. The effects of pan-NOX inhibition by isuzinaxib can be compared with the effects of the dual NOX1/NOX4 inhibitor <Ligand id=9932/> (GKT137831) <Reference id=43606/>. COVID-19: ROS production in response to virus infection are known activators that promote apoptosis, lung injury, and inflammation. Isuzinaxib is being evaluated as a clinical agent that may reduce ROS-induced tissue damage in SARS-CoV-2 infected patients.
xref: CHEMBL4650894
synonym: APX-115
synonym: APX115
synonym: EWHA-18278 (free base)
approved: f
ligand name: isuzinaxib
type: SyntheticOrganicLigand

acebilustat
in ch i key: GERJIEKMNDGSCS-DQEYMECFSA-N
in ch i: InChI=1S/C29H27N3O4/c33-29(34)23-5-1-20(2-6-23)16-31-18-25-15-24(31)19-32(25)17-21-3-9-26(10-4-21)36-27-11-7-22(8-12-27)28-30-13-14-35-28/h1-14,24-25H,15-19H2,(H,33,34)/t24-,25-/m0/s1
comment: Acebilustat (CTX-4430) is an oral leukotriene A4 hydrolase (LTA4H) inhibitor. Pharmacokinetic data indicate that it's suitable for one-daily administration. Acebilustat disrupts biosynthesis of the pro-inflammatory mediator leukotriene B4 (which is a chemoattractant and activator of inflammatory immune cells such as neutrophils), and thus has anti-inflammatory activity. The chemical structure is claimed in Celtaxsys' patent WO2014164658A1 <Reference id=43604/>. Acebilustat is under investigation for clinical utility as an inhibitor of COVID-19 inflammation.
iupac name: 4-[[(1S,4S)-5-[[4-[4-(1,3-oxazol-2-yl)phenoxy]phenyl]methyl]-2,5-diazabicyclo[2.2.1]heptan-2-yl]methyl]benzoic acid
xref: CHEMBL4297604
synonym: CTX-4430
synonym: CTX4430
approved: f
ligand name: acebilustat
type: SyntheticOrganicLigand

Example A225 [WO2012170976A2]
in ch i key: OXOXFDSEGFLWLU-UHFFFAOYSA-N
in ch i: InChI=1S/C25H26FN5O2/c1-2-21(32)31-14-12-25(26,13-15-31)16-28-24-22(23(27)29-17-30-24)18-8-10-20(11-9-18)33-19-6-4-3-5-7-19/h2-11,17H,1,12-16H2,(H3,27,28,29,30)
comment: Example A225 [WO2012170976A2] is an investigational Bruton's tyrosine kinase (BTK) inhibitor. It is a fluoropiperidin analogue of <Ligand id=9752/> and its chemical structure is claimed in Merck patent. This compound has been identified as TL-895 by online chemical resources, in which it is described as an orally-available, selective and irreversible BTK inhibitor. TL-895 was originally developed for potential to treat refractory myelofibrosis and acute myeloid leukemia (AML). COVID-19: TL-895 has been redeployed for anti-inflammatory potential in COVID-19 patients. BTK inhibition is expected to reduce production of pro-inflammatory cytokines that are associated with cytokine storm, disease progression and poor prognosis in hospitalised COVID-19 patients.
iupac name: 1-[4-[[[6-amino-5-(4-phenoxyphenyl)pyrimidin-4-yl]amino]methyl]-4-fluoropiperidin-1-yl]prop-2-en-1-one
synonym: TL895
synonym: TL-895
approved: f
ligand name: Example A225 [WO2012170976A2]
type: SyntheticOrganicLigand

compound 28 [PMID: 35439002]
in ch i key: HHZHOYGIUZUEII-DEOSSOPVSA-N
in ch i: InChI=1S/C27H30BrNO4S/c1-20-14-25(15-23(27(20)28)19-34(31,32)26-7-3-2-4-8-26)33-18-22-11-9-21(10-12-22)16-29-13-5-6-24(29)17-30/h2-4,7-12,14-15,24,30H,5-6,13,16-19H2,1H3/t24-/m0/s1
comment: This compound is a sphingosine kinase 1 inhibitor <Reference id=43573/>. It has improved anti-proliferative activity compared to <Ligand id=6623/> in in vitro and in vivo cancer models. Compound 28 is proposed for potential to induce apoptosis in solid tumours.
approved: f
ligand name: compound 28 [PMID: 35439002]
type: SyntheticOrganicLigand

vadadustat
canonical SMILES: OC(=O)CNC(=O)c1ncc(cc1O)c1cccc(c1)Cl
in ch i key: JGRXMPYUTJLTKT-UHFFFAOYSA-N
in ch i: InChI=1S/C14H11ClN2O4/c15-10-3-1-2-8(4-10)9-5-11(18)13(16-6-9)14(21)17-7-12(19)20/h1-6,18H,7H2,(H,17,21)(H,19,20)
comment: Vadadustat is an orally bioavailable HIF prolyl-hydroxylase inhibitor. It targets the enzymes PHD1, PHD2 and PHD3 to mediate an increase in endogenous erythropoietin production which delivers anti-anemia action. See also <Ligand id=11828/>.
iupac name: 2-[[5-(3-chlorophenyl)-3-hydroxypyridine-2-carbonyl]amino]acetic acid
xref: CHEMBL3646221
synonym: Vafseo®
synonym: AKB-6548
synonym: AKB6548
approved: t
ligand name: vadadustat
type: SyntheticOrganicLigand

vipivotide tetraxetan
in ch i key: JBHPLHATEXGMQR-VLOIPPKDSA-N
in ch i: InChI=1S/C49H71N9O16/c59-40(28-55-17-19-56(29-42(62)63)21-23-58(31-44(66)67)24-22-57(20-18-55)30-43(64)65)51-27-32-8-12-35(13-9-32)45(68)52-39(26-33-10-11-34-5-1-2-6-36(34)25-33)46(69)50-16-4-3-7-37(47(70)71)53-49(74)54-38(48(72)73)14-15-41(60)61/h1-2,5-6,10-11,25,32,35,37-39H,3-4,7-9,12-24,26-31H2,(H,50,69)(H,51,59)(H,52,68)(H,60,61)(H,62,63)(H,64,65)(H,66,67)(H,70,71)(H,72,73)(H2,53,54,74)/t32?,35?,37-,38-,39-/m0/s1
comment: Vipivotide tetraxetan (PSMA-617) is a potent PSMA (prostate-specific membrane antigen) inhibitor <Reference id=43597/>, that was designed for the treatrment of PSMA-positive hormone-relapsed metastatic prostate cancer. It has a DOTA moiety (= tetraxetan) that acts as a radionuclide-chelating domain.
iupac name: (2S)-2-[[(1S)-1-carboxy-5-[[(2S)-3-naphthalen-2-yl-2-[[4-[[[2-[4,7,10-tris(carboxymethyl)-1,4,7,10-tetrazacyclododec-1-yl]acetyl]amino]methyl]cyclohexanecarbonyl]amino]propanoyl]amino]pentyl]carbamoylamino]pentanedioic acid
xref: CHEMBL4594280
synonym: PSMA-617
synonym: PSMA617
approved: f
ligand name: vipivotide tetraxetan
type: SyntheticOrganicLigand

TO507
in ch i key: SPMFBZXXQBXKFX-LUOSIZPJSA-N
in ch i: InChI=1S/C26H26N6O5S/c27-17(26(35)36)7-8-38-12-19-21(33)22(34)25(37-19)32-11-16(20-23(28)30-13-31-24(20)32)6-5-14-9-15-3-1-2-4-18(15)29-10-14/h1-4,9-11,13,17,19,21-22,25,33-34H,7-8,12,27H2,(H,35,36)(H2,28,30,31)/t17-,19+,21+,22+,25+/m0/s1
comment: TO507 was reported as an inhibitor of the N7-methyltransferase (MTase) RNA capping activity of SARS-CoV-2 nsp14 <Reference id=43577/>. It is a derivative of the S-adenosyl-l-homocysteine (SAH) molecule. Nsp14 is one of two MTases in SARS-CoV-2 <Reference id=39064/><Reference id=43595/><Reference id=43596/>, and along with other SARS-CoV-2 enzymes (the proteases Mpro and PLpro, RNA-dependent RNA polymerase, helicase, endonuclease and the 2nd MTase nsp16) it is considered as a tractable target for the development of novel antivirals for COVID-19.
iupac name: S-(((2S,3S,4R,5R)-5-(4-Amino-5-(quinolin-3-ylethynyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-3,4- dihydroxytetrahydrofuran-2-yl)methyl)-L-homocysteine
synonym: compound 16 [PMID: 34152728]
synonym: TO-507
approved: f
ligand name: TO507
type: SyntheticOrganicLigand

AX15836
in ch i key: HTFNVAVTYILUCF-UHFFFAOYSA-N
in ch i: InChI=1S/C32H40N8O5S/c1-5-45-28-20-22(30(41)39-14-12-23(13-15-39)38-18-16-36(2)17-19-38)10-11-25(28)34-32-33-21-27-29(35-32)40(46(4,43)44)26-9-7-6-8-24(26)31(42)37(27)3/h6-11,20-21,23H,5,12-19H2,1-4H3,(H,33,34,35)
comment: AX15836 is reported as a selective inhibitor of ERK5 (mitogen-activated protein kinase 7; MAPK7) <Reference id=43593/>. It was designed to inhibit the catalytic function of ERK5, to offer potential for use in inflammation and oncology. AX15836 has also been reported to activate ERK5 transcriptional activity <Reference id=43594/>, which paradoxically elevates ERK5 signalling,
iupac name: 2-[2-ethoxy-4-[4-(4-methylpiperazin-1-yl)piperidine-1-carbonyl]anilino]-5-methyl-11-methylsulfonylpyrimido[4,5-b][1,4]benzodiazepin-6-one
xref: CHEMBL4541479
synonym: compound A10 [PMID: 27679845]
synonym: AX-15836
approved: f
ligand name: AX15836
type: SyntheticOrganicLigand

compound 6f [PMID: 35476936]
isomeric SMILES: O=C(c1cn(C)nc1)Nc1c(C#N)c2c(s1)CN(C(=O)Nc1ccc(OC)cc1)CC2
in ch i key: WVYHDFDOBCBKGI-UHFFFAOYSA-N
in ch i: InChI=1S/C21H20N6O3S/c1-26-11-13(10-23-26)19(28)25-20-17(9-22)16-7-8-27(12-18(16)31-20)21(29)24-14-3-5-15(30-2)6-4-14/h3-6,10-11H,7-8,12H2,1-2H3,(H,24,29)(H,25,28)
comment: This compound is a small molecule inhibitor of STAT3 phosphorylation, that was designed to inhibit proliferation and metastasis of osteosarcomas <Reference id=43592/>. It binds directly to the SH2 domain of the transcription factor.
iupac name: 3-Cyano-2-(1-methyl-1H-pyrazole-4-carboxamido)-N-(2-pyridinyl)-4,7-dihydrothieno[2,3-c]pyridine-6(5H)-carboxamide
approved: f
ligand name: compound 6f [PMID: 35476936]
type: SyntheticOrganicLigand

compound 10 [O'Mahony et al., 2022]
in ch i key: IQKNCBUBONVBNJ-UHFFFAOYSA-N
comment: This compound binds to PPARγ without any agonist activity <Reference id=43581/>. It inhibits CDK5-mediated phosphorylation of PPARγ at Ser273. Compound 10 was designed for antidiabetic potential, as an alternative to thiazolidinedione class antihyperglycemic PPARγ agonist drugs such as <Ligand id=1056/> and <Ligand id=2694/>.
approved: f
ligand name: compound 10 [O'Mahony et al., 2022]
type: SyntheticOrganicLigand

ulevostinag
in ch i key: YSUIQYOGTINQIN-CLMXYZJCSA-N
comment: Ulevostinag (MK-1454) is a small molecule STING agonist that was developed as an anti-tumour agent <Reference id=43578/>. It is a cyclic dinucleotide derivative.
synonym: MK-1454
synonym: compound 26 [PMID: 35332774]
synonym: MK1454
approved: f
ligand name: ulevostinag
type: SyntheticOrganicLigand

compound 25 [PMID: 35439007]
in ch i key: ZHVNWPYRBLBLOS-WVSUBDOOSA-N
in ch i: InChI=1S/C20H23N7O6S/c1-3-26(34(30,31)12-4-5-13(32-2)11(6-12)7-21)8-14-16(28)17(29)20(33-14)27-10-25-15-18(22)23-9-24-19(15)27/h4-6,9-10,14,16-17,20,28-29H,3,8H2,1-2H3,(H2,22,23,24)/t14-,16-,17-,20-/m1/s1
comment: This compound inhibits the N7-methyltransferase RNA capping activity of SARS-CoV-2 nsp14 <Reference id=43575/>. It is a dinucleoside mimetic of S-adenosyl-l-methionine (SAM; a.k.a. <Ligand id=4786/>) that is the methyl donor for the reaction catalysed by nsp14. Compound 25 is selective for nsp14 compared to human RNA N7-MTase (RNMT: O43148).
iupac name: N-{[(2R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl}-3-cyano-N-ethyl-4-methoxybenzene-1-sulfonamide
approved: f
ligand name: compound 25 [PMID: 35439007]
type: SyntheticOrganicLigand

5-hydroxyindole acetaldehyde
canonical SMILES: O=CCc1c[nH]c2c1cc(O)cc2
isomeric SMILES: O=CCc1c[nH]c2c1cc(O)cc2
in ch i key: OBFAPCIUSYHFIE-UHFFFAOYSA-N
in ch i: InChI=1S/C10H9NO2/c12-4-3-7-6-11-10-2-1-8(13)5-9(7)10/h1-2,4-6,11,13H,3H2
iupac name: 2-(5-hydroxy-1H-indol-3-yl)acetaldehyde
synonym: 5-hydroxyindole-3-acetaldehyde
synonym: 5-hydroxyindolylacetaldehyde
approved: f
ligand name: 5-hydroxyindole acetaldehyde
type: MetaboliteLigand

eliapixant
in ch i key: GTQPEQGDLVSFJO-CXAGYDPISA-N
comment: Eliapixant (BAY 1817080) is a selective purinergic receptor P2X 3 (P2X3) receptor antagonist. Bayer investigated this agent as a potential treatment for persistent/refractory chronic cough <Reference id=43571/> and for activity to reduce hypersensitive nerve fibers in inflammatory pain conditions <Reference id=43572/>.
iupac name: 3-(5-methyl-1,3-thiazol-2-yl)-5-[(3R)-oxolan-3-yl]oxy-N-[(1R)-1-[2-(trifluoromethyl)pyrimidin-5-yl]ethyl]benzamide
synonym: BAY-1817080
synonym: BAY1817080
approved: f
ligand name: eliapixant
type: SyntheticOrganicLigand

ABBV-CLS-484
in ch i key: DVFCRTGTEXUFIN-GFCCVEGCSA-N
in ch i: InChI=1S/C17H24FN3O4S/c1-10(2)5-6-19-12-4-3-11-7-14(22)17(16(18)13(11)8-12)21-9-15(23)20-26(21,24)25/h7,10,12,19,22H,3-6,8-9H2,1-2H3,(H,20,23)/t12-/m1/s1
comment: ABBV-CLS-484 is an inhibitor of the ptotein tyrosine phosphatases PTPN2 and PTPN1 that was developed by AbbVie, Calico Life Sciences, and the Broad Institute of MIT and Harvard, for anti-tumor potential. Its chemical structure was disclosed at the AACR spring meeting in 2022.
approved: f
ligand name: ABBV-CLS-484
type: SyntheticOrganicLigand

FHD-286
in ch i key: JBLQNFBXKOAIHG-FCEWJHQRSA-N
in ch i: InChI=1S/C24H30N6O6S2/c1-15-10-29(11-16(2)36-15)21-7-5-6-18(25-21)20-14-37-24(27-20)28-23(32)19(13-35-3)26-22(31)17-8-9-30(12-17)38(4,33)34/h5-9,12,14-16,19H,10-11,13H2,1-4H3,(H,26,31)(H,27,28,32)/t15-,16+,19-/m0/s1
comment: FHD-286 is a first-in-class oral allosteric BAF complex inhibitor. It targets the SMARCA4 (BRG1) subunit of the complex. FHD-286 was developed by Foghorn Therapeutics, and its chemical structure was disclosed at the AACR spring meeting in 2022.
iupac name: N-[(2S)-1-[[4-[6-[(2S,6R)-2,6-dimethylmorpholin-4-yl]pyridin-2-yl]-1,3-thiazol-2-yl]amino]-3-methoxy-1-oxopropan-2-yl]-1-methylsulfonylpyrrole-3-carboxamide
synonym: FHD286
approved: f
ligand name: FHD-286
type: SyntheticOrganicLigand

MRTX0902
in ch i key: ILPWEAHQRAWJIU-OAHLLOKOSA-N
in ch i: InChI=1S/C22H24N6O/c1-14-17(12-23)5-4-6-18(14)15(2)25-22-19-11-21(28-7-9-29-10-8-28)24-13-20(19)16(3)26-27-22/h4-6,11,13,15H,7-10H2,1-3H3,(H,25,27)/t15-/m1/s1
comment: MRTX0902 is an inhibitor of the SOS Ras/Rac guanine nucleotide exchange factor 1 (SOS1) that is intended to target the RAS pathway in KRAS positive tumours. It ws developed by Mirati Therapeutics and its chemical structure was disclosed at the AACR spring meeting in 2022. Full details were published in the Journal of Medicinal Chemistry in July 2022 <Reference id=43880/>. MRTX0902 disrupts the protein-protein interaction between SOS1 and KRAS, it is orally bioavailable and can cross the blood-brain barrier. SOS1 is a key activator of KRAS function, so inhibiting their interaction is being explored as novel mechanism to combat KRAS-driven cancers <Reference id=43881/><Reference id=38242/>.
synonym: MRTX-0902
approved: f
ligand name: MRTX0902
type: SyntheticOrganicLigand

CFT8634
in ch i key: GNRGNRCQXHMQQV-CPBHLAHYSA-N
in ch i: InChI=1S/C37H45F3N6O5/c1-22-23(2)36(49)43(3)19-26(22)24-16-31(50-4)27(32(17-24)51-5)20-44-11-10-33(37(39,40)21-44)46-14-12-45(13-15-46)30-8-6-25(18-28(30)38)41-29-7-9-34(47)42-35(29)48/h6,8,16-19,29,33,41H,7,9-15,20-21H2,1-5H3,(H,42,47,48)/t29-,33+/m1/s1
comment: CFT8634 is an orally bioavailable BRD9 degrader that was developed by C4 Therapeutics for potential to treat BRD9-dependent tumours. BRD9 degradation is predicted to offer a more effective option than BRD9 inhibition. Its chemical structure was disclosed at the AACR spring meeting in 2022.
synonym: CFT-8634
approved: f
ligand name: CFT8634
type: SyntheticOrganicLigand

GDC-6036
in ch i key: ZRBPIAWWRPFDPY-IRXDYDNUSA-N
comment: GDC-6036 is an oral, covalent inhibitor that targets oncogenic KRASG12C. Its chemical structure was revealed at the AACR spring meeting in 2022. It could be either example 17a or 17b (or a mixture of both) from patent US11236068B2, but these have one extra specified stereo bond; 17a (R), 17b (S) <Reference id=43901/>. We matched GDC-6036's chemical structure to the INN 'divarasib' which was published in the WHO's proposed INN list 127 on 21 July 2022.
iupac name: 1-[(3S)-4-[7-[6-amino-4-methyl-3-(trifluoromethyl)pyridin-2-yl]-6-chloro-8-fluoro-2-[[(2S)-1-methylpyrrolidin-2-yl]methoxy]quinazolin-4-yl]-3-methylpiperazin-1-yl]prop-2-en-1-one
synonym: GDC6036
synonym: GDC-6036
approved: f
ligand name: GDC-6036
type: SyntheticOrganicLigand

EZM0414
in ch i key: ZGFOQXUCQAEQHH-SJORKVTESA-N
in ch i: InChI=1S/C22H29FN4O2/c1-14-6-7-19(23)21-18(14)13-20(25-21)22(29)24-16-4-3-5-17(12-16)27-10-8-26(9-11-27)15(2)28/h6-7,13,16-17,25H,3-5,8-12H2,1-2H3,(H,24,29)/t16-,17+/m1/s1
comment: EZM0414 is a first-in-class, oral SETD2 histone methyl transferase inhibitor that was developed by Epizyme for anti-cancer potential. Its chemical structure was disclosed at the AACR spring meeting in 2022 (link to download poster pdf here).
iupac name: N-[(1R,3S)-3-(4-acetylpiperazin-1-yl)cyclohexyl]-7-fluoro-4-methyl-1H-indole-2-carboxamide
synonym: EZM-0414
approved: f
ligand name: EZM0414
type: SyntheticOrganicLigand

CFT7455
in ch i key: MUKCJOOKCZSQNW-DEOSSOPVSA-N
in ch i: InChI=1S/C28H27N3O4/c32-25-11-10-24(27(33)29-25)31-23-9-8-20(21-2-1-3-22(26(21)23)28(31)34)16-18-4-6-19(7-5-18)17-30-12-14-35-15-13-30/h1-9,24H,10-17H2,(H,29,32,33)/t24-/m0/s1
comment: CFT7455 is a monofunctional IKZF1/3 degrader that was developed by C4 Therapeutics for potential to treat relapsed/refractory multiple myeloma. It is orally bioactive.
iupac name: (3S)-3-[6-[[4-(morpholin-4-ylmethyl)phenyl]methyl]-2-oxobenzo[cd]indol-1-yl]piperidine-2,6-dione
approved: f
ligand name: CFT7455
type: SyntheticOrganicLigand

compound 53 [PMID: 33038794]
in ch i key: OEBVYNULNKSONR-UHFFFAOYSA-N
comment: This compound is a small molecule activator of STING taht was designed by Curadev Pharma for immunomodulatory potential <Reference id=43568/>. It targets a pocket in the protein's transmembrane domain <Reference id=43569/>.
approved: f
ligand name: compound 53 [PMID: 33038794]
type: SyntheticOrganicLigand

EGIS-11150
in ch i key: BQNLTXZVZWVEDX-UHFFFAOYSA-N
comment: EGIS-11150 is an antipsychotic compound that has demonstrated procognitive efficacy in preclinical models <Reference id=43559/><Reference id=43560/>. It has an 'atypical' antipsychotic drug profile, with effects on several GPCR receptor pathways within the hippocampal-prefrontal cortex circuit. It has been proposed as a modulator of psychosis and cognitive dysfunction in schizophrenia <Reference id=43560/>.
synonym: EGIS11150
synonym: S 36549
synonym: S-36549
synonym: S36549
approved: f
ligand name: EGIS-11150
type: SyntheticOrganicLigand

BMS-986176
in ch i key: RKAHOQATMSONTM-IBGZPJMESA-N
in ch i: InChI=1S/C19H23F4N3O/c1-11(2)9-19(3,24)10-27-15-5-4-13(26-16(15)18(22)23)12-6-7-25-14(8-12)17(20)21/h4-8,11,17-18H,9-10,24H2,1-3H3/t19-/m0/s1
comment: BMS-986176 (LX-9211) is a clinical stage small molecule inhibitor of AP2 associated kinase 1 (AAK1) <Reference id=43554/><Reference id=42690/>. It is CNS-penetrable, and was designed as a drug for treating neuropathic pain. Additional inhibitors (e.g. compounds 43 and 58) were also discovered, but despite good selectivity, potency and favourable efficacy in the CCI rat model (a peripheral nerve injury model of chronic neuropathic pain), their preclinical toxicity profiles were inferior to that of BMS-986176.
iupac name: (2S)-1-[2-(difluoromethyl)-6-[2-(difluoromethyl)pyridin-4-yl]pyridin-3-yl]oxy-2,4-dimethylpentan-2-amine
synonym: BMS986176
synonym: LX-9211
synonym: LX9211
approved: f
ligand name: BMS-986176
type: SyntheticOrganicLigand

Citrusinine II
canonical SMILES: COc1c(O)cc(c2c1n(C)c1c(c2=O)cccc1O)O
isomeric SMILES: COc1c(O)cc(c2c1n(C)c1c(c2=O)cccc1O)O
in ch i key: QEGXAAUCDUFHPJ-UHFFFAOYSA-N
in ch i: InChI=1S/C15H13NO5/c1-16-12-7(4-3-5-8(12)17)14(20)11-9(18)6-10(19)15(21-2)13(11)16/h3-6,17-19H,1-2H3
comment: Citrusinine II is a natural compound found in the tropical plant Atalantia monophylla. It inhibits TRPV3 channel activity in vitro (IC50 12.43 μM) <Reference id=42958/>.
iupac name: 1,3,5-trihydroxy-4-methoxy-10-methylacridin-9-one
xref: CHEMBL465847
synonym: Citrusinine-II
synonym: compound 5 [PMID: 21277783]
approved: f
ligand name: Citrusinine II
type: NaturalProductLigand

N-0385
in ch i key: JTHVOFMYRRNGPA-ACRUOGEOSA-N
in ch i: InChI=1S/C28H36N8O6S2/c1-44(41,42)36-20(13-14-23(29)37)25(39)34-21(16-17-8-3-2-4-9-17)26(40)33-19(11-7-15-32-28(30)31)24(38)27-35-18-10-5-6-12-22(18)43-27/h2-6,8-10,12,19-21,36H,7,11,13-16H2,1H3,(H2,29,37)(H,33,40)(H,34,39)(H4,30,31,32)/t19-,20-,21-/m0/s1
comment: In March 2022, N-0385 was reported as a TMPRSS2 inhibitor, that has potential to disrupt infection of human host cells by coronaviruses by blocking TMPRSS2-mediated cleavage of the viral spike glycoprotein <Reference id=43549/>. Mechanistically N-0385 operates as an 'entry inhibitor'. It is speculated that this type of inhibitor could offer prophylactic and therapeutic value across a broad range of coronaviruses (pan-coronavirus antiviral) and it appears to retain activity across SARS-CoV-2 variants. Structurally, N-0385 is a modified tripeptide. This chemical structure was claimed in pre-SARS-CoV-2 patents from Neomed Institute as a matriptase inhibitor (e.g. WO2018112648A1 <Reference id=43550/> and US2019337981A1 <Reference id=43551/>). The patents claim use for treatment or prevention of human coronavirus infections including hCoV-NL63, hCoV-OC43, hCoV-229E, hCoV-HKUI, SARS-CoV (Severe Acute Respiratory Syndrome-Corona Virus), or MERS-CoV (Middle East Respiratory Syndrome virus), in addition for potential to prevent infection by other types of viruses such as human parainfluenza viruses, and further therapeutic applications for hyperproliferative, respiratory and inflammatory disorders.
iupac name: (2S)-N-[(2S)-1-[[(2S)-1-(1,3-benzothiazol-2-yl)-5-(diaminomethylideneamino)-1-oxopentan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]-2-(methanesulfonamido)pentanediamide
synonym: N0385
synonym: Ms-QFR-Kbt
synonym: example 2 [WO2018112648A1]
approved: f
ligand name: N-0385
type: PeptideLigand

BMS-189532
in ch i key: WSQCBOJFDSJLNS-UHFFFAOYSA-N
in ch i: InChI=1S/C27H25NO3/c1-17-4-6-18(7-5-17)22-14-15-27(2,3)24-13-10-20(16-23(22)24)25(29)28-21-11-8-19(9-12-21)26(30)31/h4-14,16H,15H2,1-3H3,(H,28,29)(H,30,31)
comment: BMS-189532 is a retinoic acid receptor-α (RAR-α) selective antagonist, that was designed for activity as a non-hormonal male contraceptive <Reference id=43546/><Reference id=43547/>. Antagonising RAR-α is predicted to disrupt spermatogenesis. Despite potent antagonism of RAR-α in vitro, the compound was ineffective in vivo by oral administration. A modified chemotype with the expected in vivo effect on sperm development is represented by <Ligand id=11954/>.
iupac name: 4-[[5,5-dimethyl-8-(4-methylphenyl)-6H-naphthalene-2-carbonyl]amino]benzoic acid
xref: CHEMBL81176
synonym: BMS189532
synonym: AGN-193491
synonym: compound 2 [PMID: 24040487]
approved: f
ligand name: BMS-189532
type: SyntheticOrganicLigand

YCT529
in ch i key: QLXSCDXZOYRDAX-UHFFFAOYSA-M
in ch i: InChI=1S/C29H25NO3/c1-18-4-6-19(7-5-18)24-17-29(2,3)33-27-15-12-22(16-23(24)27)26-14-13-25(30-26)20-8-10-21(11-9-20)28(31)32/h4-17,30H,1-3H3,(H,31,32)/p-1
comment: YCT529 is an oral retinoic acid receptor alpha (RAR-α) antagonist, that is being investigated as a non-hormonal male contraceptive. Its development and function were presented at the spring meeting of the American Chemical Society (ACS) in March 2022. Antagonising RAR-α disrupts spermatogenesis. YCT529 is formulated as a sodium salt. The RAR-α-selective antagonists BMS-189532 and BMS-189614 have been reported previously <Reference id=43546/><Reference id=43547/>.
approved: f
ligand name: YCT529
type: SyntheticOrganicLigand

LY3372689
in ch i key: FRVXHWNHGWUTQO-CABZTGNLSA-N
in ch i: InChI=1S/C16H22FN5O3S/c1-9-6-12(24-8-14-19-11(3)25-21-14)4-5-22(9)7-13-15(17)20-16(26-13)18-10(2)23/h9,12H,4-8H2,1-3H3,(H,18,20,23)/t9-,12-/m0/s1
comment: LY3372689 is a O-GlcNAcase (OGA) inhibitor that was developed by Eli Lilly as a Tau modulator for Alzheimer's disease. Its structure was revealed during the 'first disclosure' session at the ACS Spring 2022 meeting, and it is the chemical structure that is claimed in Eli Lilly's patent WO2018140299A1 <Reference id=43545/>. Information from clinical trial records indicates that LY3372689 is administered orally.
iupac name: N-[4-fluoro-5-[[(2S,4S)-2-methyl-4-[(5-methyl-1,2,4-oxadiazol-3-yl)methoxy]piperidin-1-yl]methyl]-1,3-thiazol-2-yl]acetamide
synonym: LY-3372689
approved: f
ligand name: LY3372689
type: SyntheticOrganicLigand

example 100 [WO2022043374]
in ch i key: HZFDKBPTVOENNB-GAFUQQFSSA-N
comment: This compound is a coronavirus 3CL proteinase (3CLpro, Mpro) inhibitor from Hoffman La Roche's patent WO2022043374 <Reference id=43544/>. It exhibits potent inhibitory activity at 3CLpro enzymes from a range of human coronaviruses (hCoV-229E, MERS-CoV, hCoV-OC43, SARS-CoV and SARS-CoV-2) in vitro. We present this as one of the most potent broad-range inhibitors from this patent. Extensive experimental work (in suitable cell lines, virus infection models etc.) would be required to determine which example (if any) is suitable for preclinical evaluation.
iupac name: N-[(2S)-1-[(2R)-2-chloro-2-fluoro-N-{[(3S)-2-oxopyrrolidin-3-yl]methyl}acetohydrazido]-3-(1-methylcyclopropyl)-1-oxopropan-2-yl]-5-(difluoromethyl)-1,2-oxazole-3-carboxamide
approved: f
ligand name: example 100 [WO2022043374]
type: SyntheticOrganicLigand

asapiprant
in ch i key: ZMZNWNTZRWXTJU-UHFFFAOYSA-N
in ch i: InChI=1S/C24H27N3O7S/c1-17(2)34-19-4-6-20(7-5-19)35(30,31)27-12-10-26(11-13-27)18-3-8-21(24-25-9-14-32-24)22(15-18)33-16-23(28)29/h3-9,14-15,17H,10-13,16H2,1-2H3,(H,28,29)
comment: Asapiprant (S-555739) is a DP1 receptor antagonist that was developed for anti-inflammatory potential <Reference id=43541/>. It has been used in an animal model of COVID-19 to indicate that targeting the PLA2G2D-PGD2/DP1 receptor pathway provides some benefit in protecting aged mice from lethal virus infection <Reference id=43542/>. A clinical study in a select subset of human COVID-19 patients is underway (as of April 2022).
xref: CHEMBL3545043
synonym: BGE-175
synonym: BGE175
synonym: S-555739
synonym: example II-74 [US8153793B2]
approved: f
ligand name: asapiprant
type: SyntheticOrganicLigand

PF-07038124
in ch i key: KXVKOYCGACSUPP-INIZCTEOSA-N
in ch i: InChI=1S/C18H22BNO4/c1-3-6-23-18-8-13(4-5-17(18)22-2)14-7-15(11-20-10-14)16-9-19(21)24-12-16/h4-5,7-8,10-11,16,21H,3,6,9,12H2,1-2H3/t16-/m0/s1
comment: PF-07038124 is a topically administered PDE4 inhibitor that was developed as a treatment for atopic dermatitis and psoriasis. Its structure was revealed during the 'first disclosure' session at the ACS Spring 2022 meeting. This chemical structure is claimed as Example 4 in Pfizer's patent US2020108083A1 <Reference id=43539/>.
iupac name: 3-[(4R)-2-hydroxyoxaborolan-4-yl]-5-(4-methoxy-3-propoxyphenyl)pyridine
synonym: PF07038124
synonym: Example 4 [US2020108083A1]
approved: f
ligand name: PF-07038124
type: SyntheticOrganicLigand

AMG650
in ch i key: JFARSZKBZGPJGR-UHFFFAOYSA-N
in ch i: InChI=1S/C27H37FN6O4S/c1-19-17-23(31-25(29-19)34-11-7-26(2,28)8-12-34)30-24(36)21-4-3-20(32-39(37,38)16-15-35)18-22(21)33-13-9-27(5-6-27)10-14-33/h3-4,17-18,32,35H,5-16H2,1-2H3,(H,29,30,31,36)
comment: AMG650 is an oral, first in class, selective small molecule inhibitor of kinesin family member 18A (KIF18A; Q8NI77). Its structure was revealed during the 'first disclosure' session at the ACS Spring 2022 meeting. AMG650 is being investigated for anti-tumour potential in metastatic solid tumours, in particular in TP53 mutant unstable aneuploid cancers that display chromosomal instability (CIN) and which become dependent upon KIF18A activity to prevent lethal multipolar cell division. AMG650 is one of the compounds (example 11-52) that are claimed in Amgen's patent US20200239441A1 <Reference id=43538/>.
iupac name: 2-(6-azaspiro[2.5]octan-6-yl)-N-[2-(4-fluoro-4-methylpiperidin-1-yl)-6-methylpyrimidin-4-yl]-4-(2-hydroxyethylsulfonylamino)benzamide
synonym: AMG 650
synonym: AMG-650
synonym: example 11-52 [US20200239441A1]
approved: f
ligand name: AMG650
type: SyntheticOrganicLigand

BLU945
in ch i key: LIMFPAAAIVQRRD-BCGVJQADSA-N
in ch i: InChI=1S/C28H37FN6O3S/c1-17(2)20-6-7-24(35-14-19(18(35)3)16-39(5,36)37)22-13-31-27(12-21(20)22)32-26-8-10-30-28(33-26)34-11-9-25(38-4)23(29)15-34/h6-8,10,12-13,17-19,23,25H,9,11,14-16H2,1-5H3,(H,30,31,32,33)/t18-,19-,23+,25-/m1/s1
comment: BLU945 is a potent, non-covalent, and orally available EGFR inhibitor (4th generation), that was designed to inhibit the EGFR pathway and provide anti-tumour activity in NSCLC with EGFR resistance mutations (EGFR with T790M/C797S triple mutant; confers resistance to the 3rd generation EGFR inhibitor <Ligand id=7719/>). Its structure was revealed during the 'first disclosure' session at the ACS Spring 2022 meeting, and this was matched by the Guide to PHARMACOLOGY team to one of the structures (compound 150) in Blueprint Medicines' patent WO2021133809A1 <Reference id=43537/>
iupac name: N-[2-[(3S,4R)-3-fluoro-4-methoxypiperidin-1-yl]pyrimidin-4-yl]-8-[(2R,3S)-2-methyl-3-(methylsulfonylmethyl)azetidin-1-yl]-5-propan-2-ylisoquinolin-3-amine
synonym: BLU-945
synonym: BLU 945
synonym: Compound 150 [WO2021133809A1]
approved: f
ligand name: BLU945
type: SyntheticOrganicLigand

AZD9574
in ch i key: WXRCLFFPZXJCLS-UHFFFAOYSA-N
in ch i: InChI=1S/C21H22F2N6O2/c1-12-20(30)27-18-14(25-12)4-3-13(17(18)22)11-28-7-9-29(10-8-28)16-6-5-15(21(31)24-2)26-19(16)23/h3-6H,7-11H2,1-2H3,(H,24,31)(H,27,30)
comment: AZD9574 is a CNS penetrant PARP1 selective inhibitor. Its structure was revealed during the 'first disclosure' session at the ACS Spring 2022 meeting. It was reported that it had shown efficacy in an intracranial BRCA1m MDA-MB-436 xenograft model. AZD9574's chemical structure is claimed in AstraZeneca's patent WO2021260092A1 <Reference id=43540/> and its substructure is very similar to the published non-CNS penetrant PARP1 selective inhibitor <Ligand id=11526/>, but with a couple of methyl groups substituted by fluorines.
iupac name: 6-fluoro-5-[4-[(5-fluoro-2-methyl-3-oxo-4H-quinoxalin-6-yl)methyl]piperazin-1-yl]-N-methylpyridine-2-carboxamide
synonym: AZD-9574
synonym: example 20 [WO2021260092A1]
approved: f
ligand name: AZD9574
type: SyntheticOrganicLigand

JX35
isomeric SMILES: ONC(=O)c1cnc(N2CC3(CN(Cc4cn(C)c5c4ccc(C#N)c5)C3)CC2)nc1
in ch i key: WBVFFDSDELAGSY-UHFFFAOYSA-N
in ch i: InChI=1S/C22H23N7O2/c1-27-10-17(18-3-2-15(7-23)6-19(18)27)11-28-12-22(13-28)4-5-29(14-22)21-24-8-16(9-25-21)20(30)26-31/h2-3,6,8-10,31H,4-5,11-14H2,1H3,(H,26,30)
comment: JX35 is a promising antimalarial candidate from a series of compounds developed from chemical optimization of <Ligand id=7503/> <Reference id=43556/>. It is a selective inhibitor of P. falciparum histone deacetylase 1 (PfHDAC1).
iupac name: 2-{2-[(6-cyano-1-methyl-1H-indol-3-yl)methyl]-2,6-diazaspiro[3.4]octan-6-yl}-N-hydroxypyrimidine-5-carboxamide
approved: f
ligand name: JX35
type: SyntheticOrganicLigand

compound 4 [WO2022008639A1]
in ch i key: ZLWNVCRHCYIPOK-VOMOGABFSA-N
comment: Compound 4 is from a series of antimalarial hexahydropyrimidine analogues claimed in UCB Biopharma patent WO2022008639A1 <Reference id=43513/>.
iupac name: N-{3-[(4S)-2-amino-4-methyl-1-[(2S,4S)-2-methyloxan-4-yl]-6-oxo-1,4,5,6-tetrahydropyrimidin-4-yl]-2-chlorophenyl}-3,5,7-trifluoroadamantane-1-carboxamide
approved: f
ligand name: compound 4 [WO2022008639A1]
type: SyntheticOrganicLigand

TRV026
in ch i key: BMVQKFSALBOKAG-YYTVJKPMSA-N
in ch i: InChI=1S/C40H64N14O8/c1-23(2)33(53-36(59)27(49-32(56)21-45-3)9-6-16-47-40(43)44)38(61)51-29(18-24-11-13-26(55)14-12-24)37(60)50-28(8-4-5-15-41)35(58)52-30(19-25-20-46-22-48-25)39(62)54-17-7-10-31(54)34(42)57/h11-14,20,22-23,27-31,33,45,55H,4-10,15-19,21,41H2,1-3H3,(H2,42,57)(H,46,48)(H,49,56)(H,50,60)(H,51,61)(H,52,58)(H,53,59)(H4,43,44,47)/t27-,28-,29-,30-,31-,33-/m0/s1
comment: TRV026 is an angiotensin II (AngII) analogue, in which the C-terminal Phe8 residue is deleted <Reference id=40648/>. This truncation attenuates Gq-mediated signalling, and promotes β-arrestin-dependent receptor endocytosis.
xref: CHEMBL4544228
synonym: TRV-026
synonym: TRV 026
approved: f
ligand name: TRV026
type: PeptideLigand

TRV023
in ch i key: QDAXGBOWJLPIHQ-UHFFFAOYSA-N
in ch i: InChI=1S/C43H68N14O10/c1-24(2)35(56-37(61)29(52-34(59)22-47-4)10-7-17-49-43(45)46)40(64)54-31(19-26-12-14-28(58)15-13-26)38(62)53-30(9-5-6-16-44)36(60)55-32(20-27-21-48-23-50-27)41(65)57-18-8-11-33(57)39(63)51-25(3)42(66)67/h12-15,21,23-25,29-33,35,47,58H,5-11,16-20,22,44H2,1-4H3,(H,48,50)(H,51,63)(H,52,59)(H,53,62)(H,54,64)(H,55,60)(H,56,61)(H,66,67)(H4,45,46,49)
comment: TRV023 is an angiotensin II (AngII) analogue, in which the C-terminal Phe8 residue is replaced with Ala <Reference id=40648/>. This modification attenuates Gq-mediated signalling, but has no effect of β-arrestin-dependent receptor endocytosis.
xref: CHEMBL4438122
synonym: TRV 023
synonym: TRV-023
approved: f
ligand name: TRV023
type: PeptideLigand

ganaxolone
in ch i key: PGTVWKLGGCQMBR-FLBATMFCSA-N
in ch i: InChI=1S/C22H36O2/c1-14(23)17-7-8-18-16-6-5-15-13-20(2,24)11-12-21(15,3)19(16)9-10-22(17,18)4/h15-19,24H,5-13H2,1-4H3/t15-,16-,17+,18-,19-,20+,21-,22+/m0/s1
comment: Ganaxolone is a synthetic analogue of the neuroactive steroid allopregnanolone (<Ligand id=4108/>). Its anti-seizure effect is likely associated with its activity as a positive allosteric modulator of the GABAA receptor <Reference id=43525/><Reference id=43526/><Reference id=43527/>.
iupac name: 1-[(3R,5S,8R,9S,10S,13S,14S,17S)-3-hydroxy-3,10,13-trimethyl-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]ethanone
xref: CHEMBL1568698
synonym: Ztalmy®
synonym: CCD-1042
synonym: CCD1042
approved: t
ligand name: ganaxolone
type: SyntheticOrganicLigand

compound 17b [PMID: 35286086]
in ch i key: RMOTTYOBLRRJDT-XXBDBSAUSA-N
comment: This compound is a <Ligand id=4941/>-<Ligand id=1016/> hybrid molecule, that was developed to combat triple-negative breast cancer <Reference id=43524/>. It simultaneously targets both estrogen receptor and epidermal growth factor receptor (EGFR) pathways to block cancer cell growth.
approved: f
ligand name: compound 17b [PMID: 35286086]
type: SyntheticOrganicLigand

MAP855
in ch i key: WZZBNLYBHUDSHF-DHLKQENFSA-N
comment: MAP855 is an orally active, ATP-competitive MEK1/2 inhibitor that was designed for anti-tumour potential <Reference id=43523/>. It inhibits wild-type and mutant forms of MEK1/2.
iupac name: 1-[(3S,4S)-4-[8-(2-chloro-4-pyrimidin-2-yloxyphenyl)-7-fluoro-2-methylimidazo[4,5-c]quinolin-1-yl]-3-fluoropiperidin-1-yl]-2-hydroxyethanone
xref: CHEMBL3904439
synonym: MAP-855
synonym: compound 30 [PMID: 35195996]
approved: f
ligand name: MAP855
type: SyntheticOrganicLigand

AZ13824374
in ch i key: NGXAMXNWIHBLBN-JIMJEQGWSA-N
in ch i: InChI=1S/C30H39FN8O2/c1-17(2)25-26-21-9-7-6-8-19(21)14-24(28(40)33-25)38(26)29(41)23-15-22(27-35-34-18(3)39(27)36-23)32-20-10-12-37(13-11-20)16-30(4,5)31/h6-9,15,17,20,24-26,32H,10-14,16H2,1-5H3,(H,33,40)/t24-,25+,26+/m0/s1
comment: AZ13824374 is an inhibitor of the chromatin modifting enzyme ATPase family AAA domain containing 2 (ATAD2) <Reference id=43522/>. It is active in vitro and was designed for potential anti-tumour activity.
synonym: compound 5 [ PMID: 35133824]
synonym: AZ-13824374
approved: f
ligand name: AZ13824374
type: SyntheticOrganicLigand

LY3154885
in ch i key: MJDOWJUPBHLXIH-GOEBONIOSA-N
comment: LY3154885 is an orally delivered dopamine D1 receptor positive allosteric modulator (PAM) <Reference id=43521/>. It was a clinical candidate for neurological disorders.
synonym: LY-3154885
synonym: compound 5 [PMID: 35175768]
approved: f
ligand name: LY3154885
type: SyntheticOrganicLigand

betahistine
canonical SMILES: CNCCc1ccccn1
isomeric SMILES: CNCCc1ccccn1
in ch i key: UUQMNUMQCIQDMZ-UHFFFAOYSA-N
in ch i: InChI=1S/C8H12N2/c1-9-7-5-8-4-2-3-6-10-8/h2-4,6,9H,5,7H2,1H3
comment: This is an orally delivered histamine receptor modulator that has weak agonist activity at histamine H1 receptors and more potent antagonist activity at the H3 receptor subtype <Reference id=43520/>.
xref: CHEMBL24441
synonym: Vasomotal®
synonym: SERC®
synonym: OBE101
approved: t
ligand name: betahistine
type: SyntheticOrganicLigand

compound 14f [PMID: 35063894]
in ch i key: FQGLCYYIHLNVRG-GOSISDBHSA-N
in ch i: InChI=1S/C31H33N5O5S2/c1-17-3-14-24(28-33-31(38)41-34-28)25(15-17)21-8-6-20(7-9-21)18(2)36(16-19-4-5-19)30-32-26(27(42-30)22-10-11-22)29(37)35-43(39,40)23-12-13-23/h3,6-9,14-15,18-19,22-23H,4-5,10-13,16H2,1-2H3,(H,35,37)(H,33,34,38)/t18-/m1/s1
comment: This compound is an orally bioavailable inhibitor of the chemerin receptor 1 (CMKLR1) <Reference id=43518/>. It is intended to regualte IFN production by plasmacytoid dendritic cells in autoinflammatory diseases.
iupac name: N-(cyclopropanesulfonyl)-5-cyclopropyl-2-[(cyclopropylmethyl)[(1R)-1-[5'-methyl-2'-(5-oxo-2,5-dihydro-1,2,4-oxadiazol-3-yl)-[1,1'-biphenyl]-4-yl]ethyl]amino]-1,3-thiazole-4-carboxamide
approved: f
ligand name: compound 14f [PMID: 35063894]
type: SyntheticOrganicLigand

T-690
in ch i key: CQAPXPSWLDAVEG-UHFFFAOYSA-N
in ch i: InChI=1S/C22H20F3N3O4/c1-21(2,31)14-7-9-15(10-8-14)27-19(29)16-11-12-26-28(20(16)30)17-5-3-4-6-18(17)32-13-22(23,24)25/h3-12,31H,13H2,1-2H3,(H,27,29)
comment: T-690 is an orally bioactive, brain-penetrant inhibitor of UDP-glucose ceramide glucosyltransferase (a.k.a. glucosylceramide synthase) <Reference id=43517/>. It was developed for potential to treat the neurodegenerative pathology in Gaucher's disease. This mechanism may have application in other neurodegenerative conditions such as Parkinson's disease.
iupac name: N-[4-(2-hydroxypropan-2-yl)phenyl]-3-oxo-2-[2-(2,2,2-trifluoroethoxy)phenyl]pyridazine-4-carboxamide
approved: f
ligand name: T-690
type: SyntheticOrganicLigand

ASP5878
in ch i key: VDZZYOJYLLNBTD-UHFFFAOYSA-N
in ch i: InChI=1S/C18H19F2N5O4/c1-27-14-5-15(28-2)17(20)13(16(14)19)10-29-12-7-21-18(22-8-12)24-11-6-23-25(9-11)3-4-26/h5-9,26H,3-4,10H2,1-2H3,(H,21,22,24)
comment: ASP5878 is an investigational, oral pan-FGFR inhibitor that was developed for potential to combat solid tumours <Reference id=43516/><Reference id=43515/>.
iupac name: 2-[4-[[5-[(2,6-difluoro-3,5-dimethoxyphenyl)methoxy]pyrimidin-2-yl]amino]pyrazol-1-yl]ethanol
xref: CHEMBL4594428
synonym: ASP-5878
synonym: compound 27 [PMID: 35219181]
approved: f
ligand name: ASP5878
type: SyntheticOrganicLigand

atuveciclib
in ch i key: ACWKGTGIJRCOOM-HHHXNRCGSA-N
in ch i: InChI=1S/C18H18FN5O2S/c1-26-16-9-13(19)6-7-15(16)17-21-11-22-18(24-17)23-14-5-3-4-12(8-14)10-27(2,20)25/h3-9,11,20H,10H2,1-2H3,(H,21,22,23,24)/t27-/m1/s1
comment: Atuveciclib (BAY 1143572) is an orally active, selective CDK9 inhibitor <Reference id=42689/>. It was the first inhibitor of its class to enter clinical development. The potency of atuveciclib is diminished at physiological ATP concentration compared to at the low ATP concentrations used in in vitro assays, Therefore, it was used as the starting point for the development of a more optimised inhibitor <Ligand id=11686/> <Reference id=42688/>.
iupac name: 4-(4-fluoro-2-methoxyphenyl)-N-[3-[(methylsulfonimidoyl)methyl]phenyl]-1,3,5-triazin-2-amine
xref: CHEMBL4439321
synonym: BAY 1143572
synonym: BAY1143572
synonym: BAY-1143572
approved: f
ligand name: atuveciclib
type: SyntheticOrganicLigand

BMS-820132
in ch i key: OYUDYQMFVRHPIY-UHFFFAOYSA-N
in ch i: InChI=1S/C26H33N6O7P/c1-5-36-40(35,37-6-2)17-32-11-8-23(30-32)29-25(33)19-12-20(38-18(3)4)14-21(13-19)39-24-16-27-22(15-28-24)26(34)31-9-7-10-31/h8,11-16,18H,5-7,9-10,17H2,1-4H3,(H,29,30,33)
comment: BMS-820132 is an investigational oral glucokinase (hexokinase 4) partial activator that was designed for potential to treat type 2 diabetes mellitus (T2DM) <Reference id=43512/>.
iupac name: 3-[5-(azetidine-1-carbonyl)pyrazin-2-yl]oxy-N-[1-(diethoxyphosphorylmethyl)pyrazol-3-yl]-5-propan-2-yloxybenzamide
synonym: compound 31 [PMID: 35179904]
synonym: BMS820132
approved: f
ligand name: BMS-820132
type: SyntheticOrganicLigand

3,4-dihydroxymandelic acid
canonical SMILES: OC(=O)C(c1ccc(c(c1)O)O)O
isomeric SMILES: OC(=O)C(c1ccc(c(c1)O)O)O
in ch i key: RGHMISIYKIHAJW-UHFFFAOYSA-N
in ch i: InChI=1S/C8H8O5/c9-5-2-1-4(3-6(5)10)7(11)8(12)13/h1-3,7,9-11H,(H,12,13)
iupac name: 2-(3,4-dihydroxyphenyl)-2-hydroxyacetic acid
synonym: DOMA
approved: f
ligand name: 3,4-dihydroxymandelic acid
type: MetaboliteLigand

compound 2 [PMID: 28379944]
in ch i key: SYDVEZUPFQXMSM-UHFFFAOYSA-N
in ch i: InChI=1S/C37H31N7O3/c1-2-9-34-38-33-20-19-28(43(24-29-12-8-21-47-29)36(45)27-10-4-3-5-11-27)22-32(33)37(46)44(34)23-25-15-17-26(18-16-25)30-13-6-7-14-31(30)35-39-41-42-40-35/h3-8,10-22H,2,9,23-24H2,1H3,(H,39,40,41,42)
comment: This compound is a nonselective angiotensin (AT) receptor antagonist <Reference id=43506/>. It is approximately ~ten-fold selective for AT2R compared to AT1R .
iupac name: N-(furan-2-ylmethyl)-N-[4-oxo-2-propyl-3-[[4-[2-(2H-tetrazol-5-yl)phenyl]phenyl]methyl]quinazolin-6-yl]benzamide
approved: f
ligand name: compound 2 [PMID: 28379944]
type: SyntheticOrganicLigand

compound 1 [PMID: 28379944]
in ch i key: KDPHUUTUDFDLBT-UHFFFAOYSA-N
in ch i: InChI=1S/C36H29N7O2S/c1-2-33-37-31-19-18-27(42(22-24-9-4-3-5-10-24)36(45)32-13-8-20-46-32)21-30(31)35(44)43(33)23-25-14-16-26(17-15-25)28-11-6-7-12-29(28)34-38-40-41-39-34/h3-21H,2,22-23H2,1H3,(H,38,39,40,41)
comment: This compound (a.k.a. L-161,638) is a potent and orally bioavailable AT2 selective antagonist <Reference id=43506/>.
iupac name: N-benzyl-N-[2-ethyl-4-oxo-3-[[4-[2-(2H-tetrazol-5-yl)phenyl]phenyl]methyl]quinazolin-6-yl]thiophene-2-carboxamide
xref: CHEMBL289472
synonym: L-161,638
synonym: L-161638
synonym: compound 13 [Glinka et al., 1994)
approved: f
ligand name: compound 1 [PMID: 28379944]
type: SyntheticOrganicLigand

INE963
in ch i key: JYHSRMKXBAPFST-UHFFFAOYSA-N
in ch i: InChI=1S/C19H26N6O2S/c1-12(2)14-5-4-13(16(22-14)27-3)15-10-21-17-25(15)23-18(28-17)24-8-6-19(26,11-20)7-9-24/h4-5,10,12,26H,6-9,11,20H2,1-3H3
comment: INE963 is a potent antimalarial compound identified by the Novartis Institute for Tropical Diseases (NITD) during an optimization study of a series of 5-aryl-2-amino-imidazothiadiazole (ITD) derivatives <Reference id=43553/>. The compound has progressed to clinical evaluation and was awarded MMV Project of the Year (2019). The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
iupac name: 4-(aminomethyl)-1-{5-[2-methoxy-6-(propan-2-yl)pyridin-3-yl]imidazo[2,1-b][1,3,4]thiadiazol-2-yl}piperidin-4-ol
synonym: NVP-INE963
synonym: MMV1582617
approved: f
ligand name: INE963
type: SyntheticOrganicLigand

compound 1a [WO2021204952A1]
in ch i key: KYICPNWURYGJCB-BJKOFHAPSA-N
in ch i: InChI=1S/C27H20F4N4O3/c28-21-9-6-17(11-16(21)12-32)34-25(36)23-19-3-1-2-4-20(19)26(37)35(14-27(29,30)31)24(23)15-5-10-22(33-13-15)38-18-7-8-18/h1-6,9-11,13,18,23-24H,7-8,14H2,(H,34,36)/t23-,24+/m0/s1
comment: Compound 1a is from a series of novel tetrahydroisoquinoline derivatives, with antimalarial activity, claimed in patent WO2021204952A1 <Reference id=43505/>. Antimalarial potency for this series is predominantly associated with the (+) enantiomer. The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
iupac name: (3S,4S)-N-(3-cyano-4-fluorophenyl)-3-(6-cyclopropyloxypyridin-3-yl)-1-oxo-2-(2,2,2-trifluoroethyl)-3,4-dihydroisoquinoline-4-carboxamide
approved: f
ligand name: compound 1a [WO2021204952A1]
type: SyntheticOrganicLigand

LSN3318839
in ch i key: JPJWHCNGSBCZMI-HUUCEWRRSA-N
comment: The chemical structure and biological activity of LSN3318839 were disclosed in Willard et al. (2021) <Reference id=43503/>. LSN3318839 is described as a positive allosteric modulator of the glucagon-like peptide-1 receptor (GLP1R). It was used to show that GLP1R potentiation can be used as a mechanism to reduce hyperglycemia.
iupac name: (2R)-2-(2-{1-[(1R)-1-(2,6-dichloro-3-cyclopropylphenyl)ethyl]-1H-imidazo[4,5-c]pyridin-6-yl}phenyl)propanoic acid
approved: f
ligand name: LSN3318839
type: SyntheticOrganicLigand

compound VII [WO2021149692A1]
in ch i key: FIWILGQIZHDAQG-UHFFFAOYSA-N
in ch i: InChI=1S/C21H19F6N7O2/c22-20(23,24)9-36-12-3-1-11(2-4-12)8-30-17(35)13-7-14(16(29)32-15(13)28)34-10-31-18(33-34)19(5-6-19)21(25,26)27/h1-4,7,10H,5-6,8-9H2,(H,30,35)(H4,28,29,32)
comment: This is the most potent antimalarial compound from a novel series of diaminopyridines claimed in Eisai's patent WO2021149692A1 <Reference id=43504/>. The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
iupac name: 2,6-diamino-N-[[4-(2,2,2-trifluoroethoxy)phenyl]methyl]-5-[3-[1-(trifluoromethyl)cyclopropyl]-1,2,4-triazol-1-yl]pyridine-3-carboxamide
approved: f
ligand name: compound VII [WO2021149692A1]
type: SyntheticOrganicLigand

galidesivir
in ch i key: AMFDITJFBUXZQN-KUBHLMPHSA-N
in ch i: InChI=1S/C11H15N5O3/c12-11-8-6(14-3-15-11)4(1-13-8)7-10(19)9(18)5(2-17)16-7/h1,3,5,7,9-10,13,16-19H,2H2,(H2,12,14,15)/t5-,7+,9-,10+/m1/s1
comment: Galidesivir (BCX4430) is an adenosine analogue and broad-spectrum antiviral agent <Reference id=43488/>. It was originally developed as a treatment for hepatitis C infection, but has subsequently demonstrated activity against Ebola, Marburg and Zika <Reference id=43489/> viruses, and was most recently evaluated for potential to treat SARS-CoV-2 infection (COVID-19). Mechanistically it inhibits the virus' RNA-dependent RNA-polymerase (RdRp), that acts as a nonobligate RNA chain terminator.
iupac name: (2S,3S,4R,5R)-2-(4-amino-5H-pyrrolo[3,2-d]pyrimidin-7-yl)-5-(hydroxymethyl)pyrrolidine-3,4-diol
xref: CHEMBL1236524
synonym: BCX4430
synonym: BCX-4430
synonym: Immucillin-A
approved: f
ligand name: galidesivir
type: SyntheticOrganicLigand

compound 7a [PMID: 33730669]
in ch i key: USSMQJUVPNGHNK-UHFFFAOYSA-N
in ch i: InChI=1S/C21H17ClN4O2/c22-15-5-2-1-4-14(15)20-24-21-23-16-6-3-7-17(28)18(16)19(26(21)25-20)12-8-10-13(27)11-9-12/h1-2,4-5,8-11,19,27H,3,6-7H2,(H,23,24,25)
comment: This is a small molecule RXFP4 agonist <Reference id=43477/>.
approved: f
ligand name: compound 7a [PMID: 33730669]
type: SyntheticOrganicLigand

WNN0109-C011
in ch i key: CRHQDPKUNJKFEB-UHFFFAOYSA-N
in ch i: InChI=1S/C27H35N3O7S2/c1-27(2,28-18-22(31)19-37-23-13-14-26(32)25(17-23)30-38(3,33)34)16-15-20-9-11-21(12-10-20)29-39(35,36)24-7-5-4-6-8-24/h4-14,17,22,28-32H,15-16,18-19H2,1-3H3
comment: WNN0109-C011 is a small molecule dual RXFP3/4 agonist <Reference id=43438/>.
iupac name: N-[4-(3-{[2-hydroxy-3-(4-hydroxy-3-methanesulfonamidophenoxy)propyl]amino}-3-methylbutyl)phenyl]benzenesulfonamide
approved: f
ligand name: WNN0109-C011
type: SyntheticOrganicLigand

compound 10d [PMID: 34855388]
canonical SMILES: COC(=O)c1ccc(cc1)CCNC(=N)N/N=C/c1c[nH]c2c1cc(C#N)cc2C
isomeric SMILES: C(#N)c1cc2c(c[nH]c2c(c1)C)/C=N/NC(=N)NCCc1ccc(C(=O)OC)cc1
in ch i key: XIVYUSRYHWXGLX-UVHMKAGCSA-N
in ch i: InChI=1S/C22H22N6O2/c1-14-9-16(11-23)10-19-18(12-26-20(14)19)13-27-28-22(24)25-8-7-15-3-5-17(6-4-15)21(29)30-2/h3-6,9-10,12-13,26H,7-8H2,1-2H3,(H3,24,25,28)/b27-13+
comment: This compound is a small molecule dual RXFP3/4 agonist <Reference id=43437/>.
iupac name: Methyl 4-(2-{N′-[(E)-[(5-Cyano-7-methyl-1H-indol-3-yl)methylidene]amino]carbamimidamido}ethyl)benzoate
approved: f
ligand name: compound 10d [PMID: 34855388]
type: SyntheticOrganicLigand

enavogliflozin
in ch i key: KORCWPOBTZTAFI-YVTYUBGGSA-N
in ch i: InChI=1S/C24H27ClO6/c25-19-15(9-12-1-3-13(4-2-12)14-5-6-14)10-17(16-7-8-30-23(16)19)24-22(29)21(28)20(27)18(11-26)31-24/h1-4,10,14,18,20-22,24,26-29H,5-9,11H2/t18-,20-,21+,22-,24+/m1/s1
comment: Enavogliflozin (DWP16001) is a selective and competitive sodium/glucose cotransporter 2 (SGLT2; SLC5A2) inhibitor <Reference id=43421/>. The structure is identical to that of GCC5694A which was disclosed in early 2022 <Reference id=43514/>.
iupac name: (2S,3R,4R,5S,6R)-2-[7-chloro-6-[(4-cyclopropylphenyl)methyl]-2,3-dihydro-1-benzofuran-4-yl]-6-(hydroxymethyl)oxane-3,4,5-triol
xref: CHEMBL3703921
synonym: DWP16001
synonym: DWP-16001
synonym: GCC5694A
synonym: GCC-5694A
synonym: compound 14g [PMID: 34813882]
approved: f
ligand name: enavogliflozin
type: SyntheticOrganicLigand

zipalertinib
in ch i key: MKCYPWYURWOKST-INIZCTEOSA-N
in ch i: InChI=1S/C23H20N6O/c1-3-18(30)28-16-8-13(2)21-19(15-9-14-6-4-5-7-17(14)25-10-15)20-22(24)26-12-27-23(20)29(21)11-16/h3-10,12,16H,1,11H2,2H3,(H,28,30)(H2,24,26,27)/t16-/m0/s1
comment: The chemical structure for zipalertinib was revealed in WHO proposed INN list 126 (Jan 2022), in which it was described as a tyrosine kinase inhibitor and antineoplastic agent. Its SMILES matches it to the EGFR inhibitor TAS-6417 (now re-coded as CLN-081) <Reference id=43356/> via PubChem. TAS-6417 was designed to selectively target EGFR with exon 20 insertion mutations, which are well defined drivers of non-small cell lung cancer. It is an orally available compound.
xref: CHEMBL4650281
synonym: TAS-6417
synonym: TAS6417
synonym: CLN-081
synonym: CLN081
approved: f
ligand name: zipalertinib
type: SyntheticOrganicLigand

compound A [WO2022027058A1]
in ch i key: WDRJGMSUTPVXDH-KBOGUJPVSA-N
comment: This compound in an IRAK4 degrader (PROTAC) that is claimed in Kymera Therapeutics' patent WO2022027058A1 <Reference id=43420/>. It is intended as a therapeutic for B-cell lymphomas that express oncogenic mutations in MYD88, e.g. the protein variant MYD88L265P. The cereblon binding portion of the molecule is based on the structure of the immunomodulatory imide drug (IMiD) <Ligand id=7331/>. Compound A simultaneously promotes the degradation of IRAK4 and the zinc-finger transcription factors Ikaros (IKZF1) and Aiolos (IKZF3), and this mechanism synergistically targets key pro-survival pathways in B-cell lymphomas (MYD88-NFκB and IRF4-Type 1 interferon) to enhance anti-tumour activity. Kymera have an IRAK4/IMDi degrader (KT-413) in their clinical pipeline, but the name-to-structure has not been disclosed.
iupac name: N-[2-[4-[[6-[2-[[2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-4-yl]amino]ethyl]-2-azaspiro[3.3]heptan-2-yl]methyl]cyclohexyl]-5-(2-hydroxypropan-2-yl)-1,3-benzothiazol-6-yl]-6-(trifluoromethyl)pyridine-2-carboxamide
approved: f
ligand name: compound A [WO2022027058A1]
type: SyntheticOrganicLigand

compound 19 [PMID: 35142215]
in ch i key: XQFMLNUPNCXPRN-UHFFFAOYSA-N
in ch i: InChI=1S/C21H16ClN3O2/c22-17-8-4-3-6-15(17)14-9-21(10-14)19(26)25(20(27)24-21)18-12-23-11-13-5-1-2-7-16(13)18/h1-8,11-12,14H,9-10H2,(H,24,27)
comment: This compound was discovered as a noncovalent coronavirus Mpro inhibitor in a virtual screening campaign of >200 million fragments, followed by crystallographic screening and hit-to-lead optimisation <Reference id=43418/>. Binding to the SARS-CoV-2 Mpro and inhibition of its protease activity were confirmed in in vitro assays.
iupac name: 2-(2-chlorophenyl)-7-(isoquinolin-4-yl)-5,7-diazaspiro[3.4]octane-6,8-dione
approved: f
ligand name: compound 19 [PMID: 35142215]
type: SyntheticOrganicLigand

3,4-dihydroxyphenylacetaldehyde
canonical SMILES: O=CCc1ccc(c(c1)O)O
isomeric SMILES: O=CCc1ccc(c(c1)O)O
in ch i key: IADQVXRMSNIUEL-UHFFFAOYSA-N
in ch i: InChI=1S/C8H8O3/c9-4-3-6-1-2-7(10)8(11)5-6/h1-2,4-5,10-11H,3H2
iupac name: 2-(3,4-dihydroxyphenyl)acetaldehyde
synonym: DOPAL
approved: f
ligand name: 3,4-dihydroxyphenylacetaldehyde
type: MetaboliteLigand

DS-3801b free base
in ch i key: XCVUPJBVKKACQB-KJOQGJGQSA-N
in ch i: InChI=1S/C28H39N3O3/c1-20-15-25(10-7-24(20)18-31-14-13-29-21(2)17-31)30(3)28(33)23-8-11-26(12-9-23)34-27-6-4-5-22(16-27)19-32/h4-7,10,15-16,21,23,26,29,32H,8-9,11-14,17-19H2,1-3H3/t21-,23-,26-/m0/s1
comment: DS-3801b (di-L-tartrate) is a non-macrolide motilin receptor (GPR38) agonist <Reference id=43417/>. We show the structure of the parent compound 12. DS-3801b (Daiichi Sankyo) was selected as a clinical lead as a novel gastrointestinal prokinetic agent with potential to treat conditions such as gastroparesis and chronic constipation.
iupac name: (1r,4r)-4-[3-(hydroxymethyl)phenoxy]-N-methyl-N-(3-methyl-4-{[(3S)-3-methylpiperazin-1-yl]methyl}phenyl)cyclohexane-1-carboxamide
synonym: compound 12 [PMID: 35051575]
approved: f
ligand name: DS-3801b free base
type: SyntheticOrganicLigand

LEO 134310
in ch i key: NADMBBGHEQYUMJ-WDXNIXBWSA-N
in ch i: InChI=1S/C34H40N2O8/c1-21(35-32(38)29-5-3-17-41-29)31(24-10-8-23(9-11-24)22-6-7-22)43-27-14-12-25(13-15-27)34(40)44-28-4-2-16-36(19-28)33(39)26-18-30(37)42-20-26/h8-15,21-22,26,28-29,31H,2-7,16-20H2,1H3,(H,35,38)/t21-,26+,28-,29+,31-/m0/s1
comment: LEO 134310 is a non-steroidal glucocorticoid receptor (GR) agonist <Reference id=43415/>. It was optimised as a topical agent for potential to treat inflammatory skin diseases such as psoriasis. LEO 134310 is rapidly deactivated by enzymatic hydrolysis, thus limiting systemic exposure and improving its therapeutic index. It is hypothesised that LEO 134310 will be more suitable for long-term use than currently used steroidal GR agonist class anti-inflammatory drugs.
iupac name: [(3S)-1-[(3R)-5-oxooxolane-3-carbonyl]piperidin-3-yl] 4-[(1R,2S)-1-(4-cyclopropylphenyl)-2-[[(2R)-oxolane-2-carbonyl]amino]propoxy]benzoate
synonym: LEO134310
synonym: LEO-134310
approved: f
ligand name: LEO 134310
type: SyntheticOrganicLigand

5-hydroxyindoleacetic acid
canonical SMILES: OC(=O)Cc1c[nH]c2c1cc(O)cc2
isomeric SMILES: c1cc2c(cc1O)c(c[nH]2)CC(=O)O
in ch i key: DUUGKQCEGZLZNO-UHFFFAOYSA-N
in ch i: InChI=1S/C10H9NO3/c12-7-1-2-9-8(4-7)6(5-11-9)3-10(13)14/h1-2,4-5,11-12H,3H2,(H,13,14)
comment: 5-hydroxyindoleacetic acid (5-HIAA; a serotonin metabolite produced by platelets and mast cells) is reported to act via GPR35 as a neutrophil chemoattractant that recruits neutrophils to sites of inflammation <Reference id=43414/>.
iupac name: 2-(5-hydroxy-1H-indol-3-yl)acetic acid
approved: f
ligand name: 5-hydroxyindoleacetic acid
type: SyntheticOrganicLigand

remdesivir triphosphate
in ch i key: DFVPCNAMNAPBCX-LTGWCKQJSA-N
comment: Remdesivir triphosphate (GS-443902) is a metabolite of <Ligand id=10715/>. It is formed by replacement of the 5'-hydroxyl group of <Ligand id=11445/> by a triphosphate group. It inhibits RNA-dependent RNA polymerase (RdRP) activity in a range of viruses.
iupac name: [[(2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] phosphono hydrogen phosphate
xref: CHEMBL2016761
synonym: GS-443902
synonym: RDV-TP
synonym: GS-441524 triphosphate
approved: f
ligand name: remdesivir triphosphate
type: SyntheticOrganicLigand

orludodstat
in ch i key: KNVJMHHAXCPZHF-JTQLQIEISA-N
comment: Orludodstat (BAY-2402234) is an orally bioavailable dihydroorotate dehydrogenase (DHODH) inhibitor <Reference id=43363/>. DHODH is important for de novo pyrimidine synthesis, and is a molecular target for treatment of myeloid malignancies <Reference id=43365/><Reference id=43364/>.
iupac name: N-(2-chloro-6-fluorophenyl)-4-[4-ethyl-3-(hydroxymethyl)-5-oxo-1,2,4-triazol-1-yl]-5-fluoro-2-[(2S)-1,1,1-trifluoropropan-2-yl]oxybenzamide
synonym: BAY-2402234
synonym: BAY2402234
approved: f
ligand name: orludodstat
type: SyntheticOrganicLigand

compound 14 [PMID: 34333981]
in ch i key: HZHDCONQUBRRDH-UHFFFAOYSA-N
in ch i: InChI=1S/C23H29N7O/c1-2-17(15-30-8-10-31-11-9-30)12-19(3-1)28-23-26-14-21(18-4-5-18)22(29-23)25-7-6-20-13-24-16-27-20/h1-3,12-14,16,18H,4-11,15H2,(H,24,27)(H2,25,26,28,29)
comment: This is a tool compound that was identified as an inhibitor of several understudied kinases; microtubule affinity regulating kinases 1, 3 and 4 (MARK1/3/4), mitogen-activated protein kinase kinase kinase 9 (MLK1; MAP3K9) and NUAK family kinase 1 (NUAK1) <Reference id=43362/>.
iupac name: 5-cyclopropyl-4-N-[2-(1H-imidazol-5-yl)ethyl]-2-N-[3-(morpholin-4-ylmethyl)phenyl]pyrimidine-2,4-diamine
approved: f
ligand name: compound 14 [PMID: 34333981]
type: SyntheticOrganicLigand

compound 13 [PMID: 34333981]
in ch i key: OEZHSZIDGUKBRK-UHFFFAOYSA-N
comment: This is a tool compound that was identified as an inhibitor of the understudied kinases AP2 associated kinase 1 (AAK1) and BMP2 inducible kinase (BMP2K) <Reference id=43362/>.
iupac name: N-[3-[[5-bromo-4-[(4-sulfamoylphenyl)methylamino]pyrimidin-2-yl]amino]phenyl]pyrrolidine-1-carboxamide
approved: f
ligand name: compound 13 [PMID: 34333981]
type: SyntheticOrganicLigand

compound 7 [PMID: 34333981]
in ch i key: PJLYZTYJSMPZHT-UHFFFAOYSA-N
comment: This is a tool compound that was identified as an inhibitor of several understudied kinases; AP2 associated kinase 1 (AAK1), serine/threonine kinase 17a (DRAK1; STK17A), serine/threonine kinase 17b (DRAK2; STK17B) and microtubule affinity regulating kinase 1 (MARK1) <Reference id=43362/>.
iupac name: N-[3-[[5-bromo-2-[[3-methyl-1-(2,2,2-trifluoroethyl)pyrazol-4-yl]amino]pyrimidin-4-yl]amino]propyl]cyclobutanecarboxamide
approved: f
ligand name: compound 7 [PMID: 34333981]
type: SyntheticOrganicLigand

compound 6 [PMID: 34333981]
in ch i key: RDROKTFULACVDQ-UHFFFAOYSA-N
comment: This is a tool compound that was identified as an inhibitor of the understudied kinase BMP2 inducible kinase (BMP2K) <Reference id=43362/>.
iupac name: 4-[[[5-bromo-2-[3-(morpholin-4-ylmethyl)anilino]pyrimidin-4-yl]amino]methyl]benzenesulfonamide
approved: f
ligand name: compound 6 [PMID: 34333981]
type: SyntheticOrganicLigand

compound 451 [WO2021252644A1]
in ch i key: SYZOFRXZMALRGI-JYJNAYRXSA-N
in ch i: InChI=1S/C21H26F3N5O3/c1-12-5-7-29(20(32)17(12)27-11-21(22,23)24)16(8-13-2-3-13)19(31)28-15(10-25)9-14-4-6-26-18(14)30/h5,7,13-16,27H,2-4,6,8-9,11H2,1H3,(H,26,30)(H,28,31)/t14-,15-,16-/m0/s1
comment: This is one of the compounds that are claimed in Pardes Biosciences' patent as cysteine protease inhibitors, principally as inhibitors of SARS-CoV-2 main protease (Mpro, 3CLPro) <Reference id=43360/>. Pardes have a lead compound (PBI-0451) in clinical trial (Phase 1 dose escalation study in healthy subjects NCT05011812), but they have not declared PBI-0451's chemical structure.
iupac name: (2S)-N-[(1S)-1-cyano-2-[(3S)-2-oxopyrrolidin-3-yl]ethyl]-3-cyclopropyl-2-[4-methyl-2-oxo-3-(2,2,2-trifluoroethylamino)pyridin-1-yl]propanamide
synonym: compound 451 [WO2021252644A1]
approved: f
ligand name: compound 451 [WO2021252644A1]
type: SyntheticOrganicLigand

vicasinabin
in ch i key: MAYZWDRUFKUGGP-VIFPVBQESA-N
in ch i: InChI=1S/C15H22N10O/c1-15(2,3)14-16-12(24-6-5-9(26)7-24)11-13(17-14)25(21-19-11)8-10-18-20-22-23(10)4/h9,26H,5-8H2,1-4H3/t9-/m0/s1
comment: The chemical structure for vicasinabin was revealed in WHO proposed INN list 126 (Jan 2022), in which it was described as a cannabinoid 2 (CB2) receptor agonist. It is one of the compounds that are claimed in Hoffmann-La Roche's patent WO2013068306A1 <Reference id=43357/>. Based on structural evidence from a 'first disclosures' session at the XXVll EFMC International Symposium on Medicinal Chemistry in September 2022, vicasinabin appears to be Roche's oral, clinical lead compound RG7774, which is proposed as a treatment for diabetic retinopathy.
iupac name: (3S)-1-[5-tert-butyl-3-[(1-methyltetrazol-5-yl)methyl]triazolo[4,5-d]pyrimidin-7-yl]pyrrolidin-3-ol
synonym: Example 151 [WO2013068306A1]
synonym: RG7774
synonym: RG-7774
approved: f
ligand name: vicasinabin
type: SyntheticOrganicLigand

zilurgisertib
in ch i key: KPRPFTOLWQQUAV-OCVAFRRMSA-N
in ch i: InChI=1S/C30H38N4O3/c31-26-25(27(35)33-28-7-10-29(36,11-8-28)12-9-28)15-21(17-32-26)20-1-3-22(4-2-20)30-16-23(30)18-34(19-30)24-5-13-37-14-6-24/h1-4,15,17,23-24,36H,5-14,16,18-19H2,(H2,31,32)(H,33,35)/t23-,28?,29?,30+/m1/s1
comment: The chemical structure for zilurgisertib was revealed in WHO proposed INN list 126 (Jan 2022), in which it was described as a serine/threonine kinase inhibitor. It is one of the compounds that are claimed in Novartis' ALK2 (ACVR1) inhibitor patent US20210155606A1 <Reference id=43355/>, and it is also claimed in WO2021257532A1 by Incyte as %22Compound A%22 <Reference id=43645/>. Incyte have declared an ALK2 inhibitor (INCB00928) in their development pipeline, but the name-to-structure has not been formally disclosed. ALK2/ACVR1 is a serine/threonine protein kinase receptor for type I bone morphogenic protein (BMP), and this signalling pathway is crucial in bone formation, and hyperactivty of the pathway is associated with diseases that are characterised by bone malformation, such as fibrodysplasia ossificans progressiva (FOP). ALK2 is also involved in the maintenance of iron homeostasis by governing production of the iron regulatory hormone hepcidin. Elevated hepcidin is thought to be a powerful driver of the pathophysiology of anemia that's associated with chronic disease. Inhibition of ALK2 upstream of hepcidin should increase circulating iron levels. Thus direct inhibition of ALK2/ACVR1 is a molecular mechanism that is being expolited for therapeutic potential in FOP and anemia arising from chronic kidney disease or myeloproliferative diseases.
iupac name: 2-amino-N-(4-hydroxy-1-bicyclo[2.2.2]octanyl)-5-[4-[(1R,5S)-3-(oxan-4-yl)-3-azabicyclo[3.1.0]hexan-1-yl]phenyl]pyridine-3-carboxamide
synonym: example 34 [US20210155606A1]
synonym: Compound A [WO2021257532A1]
approved: f
ligand name: zilurgisertib
type: SyntheticOrganicLigand

tinengotinib
in ch i key: DQFCVOOFMXEPOC-UHFFFAOYSA-N
in ch i: InChI=1S/C20H19ClN6O/c1-12-18-20(26-25-12)23-16-10-17(27-6-8-28-9-7-27)22-11-14(16)19(24-18)13-4-2-3-5-15(13)21/h2-5,10-11H,6-9H2,1H3,(H2,23,25,26)
comment: The chemical structure for tinengotinib was revealed in WHO proposed INN list 126 (Jan 2022), in which it was described as a tyrosine kinase inhibitor and antineoplastic agent. The SMILES provided a match to TransThera Sciences' clinical lead TT-00420 via PubChem. TT-00420 appears to be an orally administered multi‐kinase inhibitor that targets cell proliferation, angiogenesis, and immune-oncology, through inhibition of Aurora kinases A/B and Janus kinases (involved in cytokine signalling) and receptor tyrosine kinases such as FGFRs and VEGFRs (which play roles in proliferation and angiogenesis) <Reference id=43354/>.
iupac name: 5-(2-chlorophenyl)-3-methyl-8-(morpholin-4-yl)-1,10-dihydropyrazolo[4,3-b]pyrido[4,3-e][1,4]diazepine
synonym: TT-00420
synonym: TT00420
synonym: Example 6 [US10889586B2]
approved: f
ligand name: tinengotinib
type: SyntheticOrganicLigand

sovleplenib
in ch i key: NJIAKNWTIVDSDA-FQEVSTJZSA-N
in ch i: InChI=1S/C24H30N6O3S/c1-34(31,32)30-11-6-18(7-12-30)17-2-4-19(5-3-17)21-14-22-23(27-9-8-26-22)24(29-21)28-16-20-15-25-10-13-33-20/h2-5,8-9,14,18,20,25H,6-7,10-13,15-16H2,1H3,(H,28,29)/t20-/m0/s1
comment: The chemical structure for sovleplenib was revealed in WHO proposed INN list 126 (Jan 2022), in which it was described as a tyrosine kinase inhibitor and antineoplastic agent. It is one of the compounds that is claimed in Hutchison Medipharma's SYK inhibitor patent WO2012167733A1 <Reference id=43350/>. Hutchison Medipharma's pipeline page refers to one SYK inhibitor with company code HMPL-523, that is in clinical development. We speculate that sovleplenib could be HMPL-523, but as of Feb. 2022 this name-to-structure has not been disclosed.
synonym: compound 225 [WO2012167733A1]
approved: f
ligand name: sovleplenib
type: SyntheticOrganicLigand

tanuxiciclib
canonical SMILES: Cc1nc(N)nc(c1)c1nc(ccc1O)c1ccnc(c1F)N
isomeric SMILES: Nc1nccc(c1F)c1nc(c(cc1)O)c1nc(nc(c1)C)N
in ch i key: UQHDKUFLWKTTDL-UHFFFAOYSA-N
in ch i: InChI=1S/C15H13FN6O/c1-7-6-10(22-15(18)20-7)13-11(23)3-2-9(21-13)8-4-5-19-14(17)12(8)16/h2-6,23H,1H3,(H2,17,19)(H2,18,20,22)
comment: The chemical structure for tanuxiciclib was revealed in WHO proposed INN list 126 (Jan 2022), in which it was described as a cyclin dependent kinase inhibitor. It is one of the examples that are claimed in Beyond Bio's patent WO2016126085A2 <Reference id=43352/>. In this patent data is provided for anti-proliferative activity against HCT116 human colon cancer cells.
iupac name: 6-(2-amino-3-fluoropyridin-4-yl)-2-(2-amino-6-methylpyrimidin-4-yl)pyridin-3-ol
synonym: example 24 [WO2016126085A2]
approved: f
ligand name: tanuxiciclib
type: SyntheticOrganicLigand

safusidenib
in ch i key: BOOMBLZEOHXPPX-BQYQJAHWSA-N
comment: The chemical structure for safusidenib was revealed in WHO proposed INN list 126 (Jan 2022), in which it was described as an antineoplastic agent. Chemical SMILES match this structure to the mutant IDH1 inhibitor DS-1001b (Daiichi Sankyo) <Reference id=43348/><Reference id=43349/>, which is a Phase 2 clinical candidate. DS-1001b is orally bioavaliable and is able to cross the blood-brain-barrier.
iupac name: (E)-3-[1-[5-(2-fluoropropan-2-yl)-3-(2,4,6-trichlorophenyl)-1,2-oxazole-4-carbonyl]-3-methylindol-4-yl]prop-2-enoic acid
xref: CHEMBL4651002
synonym: DS-1001B
approved: f
ligand name: safusidenib
type: SyntheticOrganicLigand

safimaltib
in ch i key: APWRZPQBPCAXFP-UHFFFAOYSA-N
in ch i: InChI=1S/C20H11F6N5O2/c21-19(22,23)15-8-10(4-6-27-15)30-18(33)13-9-29-31(16(13)20(24,25)26)14-3-1-2-12-11(14)5-7-28-17(12)32/h1-9H,(H,28,32)(H,27,30,33)
comment: The chemical structure for safimaltib was revealed in WHO proposed INN list 126 (Jan 2022), in which it was described as a mucosa-associated lymphoid tissue lymphoma translocation protein 1 (MALT1) inhibitor and antineoplastic agent. It is one of the examples claimed in Janssen Biotech's patent WO2018119036A1 <Reference id=43347/>.
synonym: example 158 [WO2018119036A1]
approved: f
ligand name: safimaltib
type: SyntheticOrganicLigand

revumenib
in ch i key: FRVSRBKUQZKTOW-YOCNBXQISA-N
in ch i: InChI=1S/C32H47FN6O4S/c1-5-39(23(3)4)31(40)27-17-25(33)9-12-28(27)43-29-18-34-22-35-30(29)38-20-32(21-38)13-15-37(16-14-32)19-24-7-10-26(11-8-24)36-44(41,42)6-2/h9,12,17-18,22-24,26,36H,5-8,10-11,13-16,19-21H2,1-4H3/t24-,26-
comment: The chemical structure for revumenib was revealed in WHO proposed INN list 126 (Jan 2022), in which it was described as an antineoplastic agent. It resolved to Syndax Pharmaceuticals' SNDX-5613 via a PubChem match on SMILES. SNDX-5613 inhbits the Menin-MLL protein-protein interaction, as a strategy that's being investigated to treat MLL-rearranged leukemias (such as ALL and AML) <Reference id=43346/>. Menin inhibitors promote differentiation and apoptosis of MLL-rearranged AML cells in vitro.
xref: CHEMBL4650827
synonym: SNDX-5613
synonym: SNDX5613
approved: f
ligand name: revumenib
type: SyntheticOrganicLigand

povorcitinib
in ch i key: MSGYSFWCPOBHEV-AWEZNQCLSA-N
in ch i: InChI=1S/C23H22F5N7O/c1-12-20(13(2)33-32-12)15-8-30-35(9-15)22(4-5-29)10-34(11-22)19-7-17(24)16(6-18(19)25)21(36)31-14(3)23(26,27)28/h6-9,14H,4,10-11H2,1-3H3,(H,31,36)(H,32,33)/t14-/m0/s1
comment: The chemical structure for povorcitinib was revealed in WHO proposed INN list 126 (Jan 2022), in which it was described as a Janus kinase inhibitor and anti-inflammatory agent. It is one of the examples claimed in Incyte's JAK inhibitor patent US20210238168A1 <Reference id=43345/>, which indicates selectivity for JAK1. Information on Incyte's pipeline page suggests that povorcitinib may be their JAK1 inhibitor clinical lead INCB54707, however as of Feb 2022 there has been no formal name-to-structure disclosure.
iupac name: 4-[3-(cyanomethyl)-3-[4-(3,5-dimethyl-1H-pyrazol-4-yl)pyrazol-1-yl]azetidin-1-yl]-2,5-difluoro-N-[(2S)-1,1,1-trifluoropropan-2-yl]benzamide
synonym: compound 7 [US20210238168A1]
approved: f
ligand name: povorcitinib
type: SyntheticOrganicLigand

paltimatrectinib
in ch i key: FYPXPQSPRRZJCK-MRXNPFEDSA-N
in ch i: InChI=1S/C20H15F5N6/c21-13-3-4-15(22)14(8-13)16-2-1-6-29(16)18-5-7-30-19(28-18)17(10-27-30)31-11-12(9-26-31)20(23,24)25/h3-5,7-11,16H,1-2,6H2/t16-/m1/s1
comment: The chemical structure for paltimatrectinib was revealed in WHO proposed INN list 126 (Jan 2022), in which it was described as a tyrosine kinase inhibitor and antineoplastic agent. It is one of the compounds claimed in Pyramid Biosciences' TRK inhibitor patent US20210094956A1 <Reference id=43343/>. Paltimatrectinib may be Pyramid's clinical candidate pan-TRK inhibitor PBI-200, that is being evaluated in TRK fusion cancers, but as of Feb 2022 there has been no formal name-to-structure disclosure. An abstract from the 2019 AACR meeting in Atlanta (USA) describes PBI-200 <Reference id=43344/>.
iupac name: 5-[(2R)-2-(2,5-difluorophenyl)pyrrolidin-1-yl]-3-[4-(trifluoromethyl)pyrazol-1-yl]pyrazolo[1,5-a]pyrimidine
synonym: example I-147 [US20210094956A1]
approved: f
ligand name: paltimatrectinib
type: SyntheticOrganicLigand

narazaciclib
in ch i key: VADOZMZXXRBXNY-UHFFFAOYSA-N
in ch i: InChI=1S/C24H27N7O/c1-29-10-12-30(13-11-29)20-8-6-19(7-9-20)27-24-26-16-18-14-17(15-25)23(32)31(22(18)28-24)21-4-2-3-5-21/h6-9,14,16,21H,2-5,10-13H2,1H3,(H,26,27,28)
comment: The chemical structure for narazaciclib was revealed in WHO proposed INN list 126 (Jan 2022), in which it was described as an cyclin dependent kinase (CDK) inhibitor and antineoplastic agent. We matched the structure to Onconova Therapeutics' clinical candidate ON123300 via PubChem. This compound was reported as a CDK4 and AMPK-related kinase 5 (ARK5 a.k.a. NUAK family kinase 1; NUAK1) inhibitor in 2014 <Reference id=43342/>. It is being administered orally in clinical trial.
xref: CHEMBL3115681
synonym: compound 7x [PMID: 24417566]
synonym: ON123300
synonym: ON-123300
synonym: ON 123300
approved: f
ligand name: narazaciclib
type: SyntheticOrganicLigand

ivarmacitinib
in ch i key: DNBCBAXDWNDRNO-FOSCPWQOSA-N
in ch i: InChI=1S/C18H22N8O2S/c1-25(15-13-3-4-19-14(13)20-9-21-15)12-5-10-7-26(8-11(10)6-12)18(27)23-17-22-16(28-2)24-29-17/h3-4,9-12H,5-8H2,1-2H3,(H,19,20,21)(H,22,23,24,27)/t10-,11+,12?
comment: Ivarmacitinib (SHR0302) is an oral Janus kinase (JAK) inhibitor, with selectivity for JAK1. It is being investigated for anti-inflammatory potential in auto-inflammatory diseases <Reference id=43337/><Reference id=43338/><Reference id=43339/>. Likely to be administered as the bisulfate salt as outlined in patent WO2014194741A1 <Reference id=43340/>.
iupac name: (3aS,6aR)-N-(3-methoxy-1,2,4-thiadiazol-5-yl)-5-[methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino]-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrole-2-carboxamide
synonym: SHR0302
synonym: SHR-0302
synonym: example 34 [WO2013091539A1]
approved: f
ligand name: ivarmacitinib
type: SyntheticOrganicLigand

iruplinalkib
in ch i key: ZPCCNHQDFZCULN-UHFFFAOYSA-N
comment: The chemical structure for iruplinalkib was revealed in WHO proposed INN list 126 (Jan 2022), in which it was described as a tyrosine kinase inhibitor and antineoplastic agent. It is one of the compounds claimed in Qilu Pharmaceutical's ALK inhibitor patent US10053477B2 <Reference id=43336/>.
iupac name: 5-chloro-4-N-(2-dimethylphosphorylphenyl)-2-N-[2-methoxy-4-(9-methyl-3,9-diazaspiro[5.5]undecan-3-yl)phenyl]pyrimidine-2,4-diamine
synonym: example 9 [US10053477B2]
approved: f
ligand name: iruplinalkib
type: SyntheticOrganicLigand

gilmelisib
in ch i key: BXKBZQAZYOZHJY-UHFFFAOYSA-N
comment: he chemical structure for gilmelisib was revealed in WHO proposed INN list 126 (Jan 2022), in which it was described as an antineoplastic agent. The chemical structure is claimed in a patent WO2015192760A1, which indicates that it is a PI3K inhibitor <Reference id=43334/>.
iupac name: 2-chloro-N-[5-[3-[2-(dimethylamino)ethoxy]-4-oxopyrido[1,2-a]pyrimidin-7-yl]-2-methoxypyridin-3-yl]-4-fluorobenzenesulfonamide
synonym: compound 25 [WO2015192760A1]
approved: f
ligand name: gilmelisib
type: SyntheticOrganicLigand

envonalkib
in ch i key: BVGDAZBTIVRTGO-UONOGXRCSA-N
comment: Envonalkib is described as a tyrosine kinase inhibitor and antineoplastic in the WHO proposed INN list 126 (Jan 2022). This chemical structure is claimed in patent WO2014117718A1, which suggests that it is an ALK inhibitor <Reference id=43332/>.
iupac name: 3-[(1R)-1-(2,6-dichloro-3-fluorophenyl)ethoxy]-5-[4-methoxy-6-[(2S)-2-methylpiperazin-1-yl]pyridin-3-yl]pyridin-2-amine
synonym: example 27 [WO2014117718A1]
approved: f
ligand name: envonalkib
type: SyntheticOrganicLigand

UM-9
in ch i key: QVVPJFBYFYYVDM-NSHDSACASA-N
in ch i: InChI=1S/C18H20O6/c1-21-14-7-5-12(17(22-2)15(14)20)11-8-10-4-6-13(19)18(23-3)16(10)24-9-11/h4-7,11,19-20H,8-9H2,1-3H3/t11-/m0/s1
comment: UM-9 (duartin) is a plant-derived isoflavone compound that can be isolated from Kaempferia parviflora (Thai ginseng). It has been demonstrated to act as an inhibitor of TPC2 channels <Reference id=43304/>. Blocking TPC2 in vitro increases melanin production in melanosomes, and inhibits proliferation, migration and invasion of melanoma cells.
iupac name: (3R)-3-(3-hydroxy-2,4-dimethoxyphenyl)-8-methoxy-3,4-dihydro-2H-chromen-7-ol
synonym: Duartin
synonym: UM9
synonym: 7,3'-Dihydroxy-2',4',8-trimethoxyisoflavan
approved: f
ligand name: UM-9
type: SyntheticOrganicLigand

enbezotinib
in ch i key: DQWACWSBFOTIDY-OUPFIFMPSA-N
in ch i: InChI=1S/C22H22FN5O3/c1-11-7-24-21(29)16-9-26-28-10-18-19(27-20(16)28)15(14-3-2-4-17(14)31-18)6-12-5-13(23)8-25-22(12)30-11/h5,8-11,14-15,17H,2-4,6-7H2,1H3,(H,24,29)/t11-,14-,15?,17+/m0/s1
comment: Enbezotinib was included in the WHO's list 126 of proposed INNs in January 2022. It was classified as a tyrosine kinase inhibitor and antineoplastic in that list. We drew the chemical structure from the INN document.
approved: f
ligand name: enbezotinib
type: SyntheticOrganicLigand

polvitolimod
in ch i key: NPRYCHLHHVWLQZ-TURQNECASA-N
in ch i: InChI=1S/C13H14FN5O4/c1-2-3-18-6-4-16-12(15)17-10(6)19(13(18)22)11-9(21)8(14)7(5-20)23-11/h1,4,7-9,11,20-21H,3,5H2,(H2,15,16,17)/t7-,8-,9-,11-/m1/s1
comment: Polvitolimod is classified as a toll-like receptor agonist in WHO proposed INN list 126 (January 2022). It was included in the 'COVID' section of that list. Patent mining suggests that polvitolimod is a TLR7 agonist prodrug, that was developed by Primmune Therapeutics as a potential treatment of cancer and infectious disease. In patent WO2019226977 polvitolimod's chemical structure matches that of Compound 32 <Reference id=43588/>. Assessment of Primmune Therapeutics' pipeline indicates that polvitolimod is likely to be their clinical candidate PRTX007. If this is the correct name-to-structure association the active drug (PRX034) is likely to be compound 27 as claimed in the patent.
iupac name: 2-amino-9-[(2R,3S,4S,5R)-4-fluoro-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-7-prop-2-ynylpurin-8-one
synonym: compound 32 [WO2019226977A1]
approved: f
ligand name: polvitolimod
type: SyntheticOrganicLigand

abimtrelvir
canonical SMILES: Cc1cncc(c1)n1c(=O)[nH]/c(=N/c2cc3cn(nc3cc2Cl)C)/n(c1=O)Cc1cc(F)c(c(c1)F)F
in ch i key: FTIFIZZEWIBTMR-UHFFFAOYSA-N
comment: Abimtrelvir is a newly proposed INN for an antiviral that was revealed in January 2022, in the COVID special section of Proposed List 126. It is therefore assumed to target SARS-CoV-2, and to be a potential drug for the treatment of patients with SARS-CoV-2 infection (COVID-19). Abimtrelvir appears to be from the same chemical series as <Ligand id=11871/>.
iupac name: (6E)-6-[(6-chloro-2-methyl-2H-indazol-5-yl)imino]-3-(5-methylpyridin-3-yl)-1-[(3,4,5-trifluorophenyl)methyl]-1,3,5-triazinane-2,4-dione
approved: f
ligand name: abimtrelvir
type: SyntheticOrganicLigand

elzovantinib
in ch i key: UUDPUQDMSHQSKH-NSHDSACASA-N
in ch i: InChI=1S/C20H20FN7O2/c1-3-27-10-13-12(8-22)14(21)4-5-15(13)30-11(2)9-24-20(29)17-18(23)26-28-7-6-16(27)25-19(17)28/h4-7,11H,3,9-10H2,1-2H3,(H2,23,26)(H,24,29)/t11-/m0/s1
comment: Elzovantinib (TPX-0022) is a MET tyrosine kinase inhibitor that targets the SRC and CSF1R pathways in cancers <Reference id=43331/>. It has demonstrated activity in patients with MET-driven gastric cancer in Phase 1 clinical trial.
synonym: TPX-0022
synonym: compound 5 [WO2019023417A1]
synonym: CSF1R-IN-2
synonym: TPX002
approved: f
ligand name: elzovantinib
type: SyntheticOrganicLigand

bezuclastinib
in ch i key: NVSHVYGIYPBTEZ-UHFFFAOYSA-N
in ch i: InChI=1S/C19H17N5O/c1-11-12(2)23-24-17(11)19(25)21-15-8-14-9-16(22-18(14)20-10-15)13-6-4-3-5-7-13/h3-10H,1-2H3,(H,20,22)(H,21,25)(H,23,24)
comment: Bezuclastinib (CGT9486; formerly PLX-9486) is a KIT inhibitor that was designed for anti-tumour potential, particularly for tumours that carry KIT mutations that confer resistance to imatinib <Reference id=43330/>.
iupac name: 4,5-dimethyl-N-(2-phenyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-1H-pyrazole-3-carboxamide
synonym: PLX-9486
synonym: PLX9486
approved: f
ligand name: bezuclastinib
type: SyntheticOrganicLigand

avutometinib
in ch i key: LMMJFBMMJUMSJS-UHFFFAOYSA-N
in ch i: InChI=1S/C21H18FN5O5S/c1-12-15-5-4-14(31-21-25-7-3-8-26-21)11-17(15)32-20(28)16(12)10-13-6-9-24-19(18(13)22)27-33(29,30)23-2/h3-9,11,23H,10H2,1-2H3,(H,24,27)
comment: Avutometinib (CH5126766; Ro5126766) is a small molecule that acts to inhibit p-MEK and p-ERK downstream of the c-RAF/MEK1 interaction <Reference id=43328/><Reference id=43329/>. It inhibits the proliferation of BRAFV600E and KRAS mutant cell lines in vitro. Avutometinib is orally active.
xref: CHEMBL3264002
synonym: RO5126766
synonym: RO-5126766
synonym: CH5126766
synonym: CH-5126766
synonym: RG-7304
synonym: compound 1 [PMID: 24900832]
synonym: VS-6766
approved: f
ligand name: avutometinib
type: SyntheticOrganicLigand

amredobresib
in ch i key: JLUUVUUYIXBDCG-UHFFFAOYSA-N
in ch i: InChI=1S/C26H29N9/c1-18-30-31-26-24(27-2)28-22(17-34(18)26)25-29-21-10-9-20(33-13-11-32(3)12-14-33)15-23(21)35(25)16-19-7-5-4-6-8-19/h4-10,15,17H,11-14,16H2,1-3H3,(H,27,28)
comment: amredobresib is a BRD4 inhibitor from Boehringer Ingelheim's patent US9266891B2 <Reference id=43327/>. It was designed for antineoplastic potential.
xref: CHEMBL3919831
synonym: example III-13 [US9266891B2]
approved: f
ligand name: amredobresib
type: SyntheticOrganicLigand

ensifentrine
in ch i key: CSOBIBXVIYAXFM-UHFFFAOYSA-N
in ch i: InChI=1S/C26H31N5O4/c1-15-10-16(2)24(17(3)11-15)29-23-14-20-19-13-22(35-5)21(34-4)12-18(19)6-8-30(20)26(33)31(23)9-7-28-25(27)32/h10-14H,6-9H2,1-5H3,(H3,27,28,32)
comment: Ensifentrine (RPL-554) is an inhibitor of phosphodiesterases 3 and 4 (PDE3 and PDE4) <Reference id=43317/>. It has bronchodilatory action <Reference id=43318/><Reference id=43319/> that is associated with short-term improvement in lung function <Reference id=43320/>, and has been investigated for therapeutic potential in asthma and chronic obstructive pulmonary disease (COPD). Ensifentrine also has anti-inflammatory effects in vitro (e.g. reducing TNFα release from human monocytes) and in vivo. Anti-inflammatory action in bronchial epithelial cells from cystic fibrosis patients is likely mediated via inhibition of PDE4 isozymes <Reference id=43323/>. Ensifentrine is active when delivered orally or by inhalation <Reference id=43322/>. COVID-19: A pilot study of ensifentrine in hospitalised COVID-19 patients was initiated in mid-late 2020.
iupac name: 2-[9,10-dimethoxy-4-oxo-2-(2,4,6-trimethylphenyl)imino-6,7-dihydropyrimido[6,1-a]isoquinolin-3-yl]ethylurea
xref: CHEMBL4594287
synonym: RPL554
approved: f
ligand name: ensifentrine
type: SyntheticOrganicLigand

PF-04885614
canonical SMILES: FC(Oc1ccc(cc1)c1c[nH]c(n1)C(N)(C)C)(F)F
isomeric SMILES: CC(C)(c1[nH]cc(n1)c1ccc(cc1)OC(F)(F)F)N
in ch i key: AGORGFNWYAUYSU-UHFFFAOYSA-N
in ch i: InChI=1S/C13H14F3N3O/c1-12(2,17)11-18-7-10(19-11)8-3-5-9(6-4-8)20-13(14,15)16/h3-7H,17H2,1-2H3,(H,18,19)
comment: PF-04885614 is reported as an orally bioavailable, selective inhibitor of Nav1.8 <Reference id=43313/>. Although it exhibits good potency, subtype selectivity and favourable in vivo pharmacokinetics, its poses a hERG liability (IC50 <2 μM).
iupac name: 2-[5-[4-(trifluoromethoxy)phenyl]-1H-imidazol-2-yl]propan-2-amine
xref: CHEMBL4084106
synonym: PF-04885614
synonym: compound 13 [Bagal et al., 2016]
approved: f
ligand name: PF-04885614
type: SyntheticOrganicLigand

KDU691
in ch i key: TYMFFISSODJRDV-UHFFFAOYSA-N
in ch i: InChI=1S/C22H18ClN5O2/c1-24-21(29)15-5-3-14(4-6-15)19-11-26-20-12-25-18(13-28(19)20)22(30)27(2)17-9-7-16(23)8-10-17/h3-13H,1-2H3,(H,24,29)
comment: KDU691 is an inhibitor of P. falciparum phosphatidylinositol 4-kinase beta (PfPI4Kβ) with a novel imidazopyrazine core <Reference id=34003/>. The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
iupac name: N-(4-chlorophenyl)-N-methyl-3-[4-(methylcarbamoyl)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide
xref: CHEMBL3325608
synonym: KDU-691
synonym: KDU 691
approved: f
ligand name: KDU691
type: SyntheticOrganicLigand

PRU-12
in ch i key: LURXOLBKAUTYIC-SLHNCBLASA-N
in ch i: InChI=1S/C20H26O2/c1-12(21)13-3-5-15-14(11-13)4-6-17-16(15)9-10-20(2)18(17)7-8-19(20)22/h3,5,11,16-19,22H,4,6-10H2,1-2H3/t16-,17-,18+,19+,20+/m1/s1
comment: PRU-12 is a structural analogue of <Ligand id=11860/>. Like its parent it has inhibitory action at the cation channel TRMPL1 <Reference id=43308/>.
iupac name: 1-[(8R,9S,13S,14S,17S)-17-hydroxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-yl]ethanone
synonym: 1-[17beta-Hydroxy-1(10),2,4-estratriene-3-yl]ethanone
synonym: PRU12
approved: f
ligand name: PRU-12
type: SyntheticOrganicLigand

PRU-10
in ch i key: YVQVEUUGNXBURX-SLHNCBLASA-N
in ch i: InChI=1S/C20H26O/c1-3-13-4-6-15-14(12-13)5-7-17-16(15)10-11-20(2)18(17)8-9-19(20)21/h3-4,6,12,16-19,21H,1,5,7-11H2,2H3/t16-,17-,18+,19+,20+/m1/s1
comment: PRU-10 is a structural analogue of <Ligand id=11860/>. Like its parent it has inhibitory action at the cation channel TRMPL1 <Reference id=43308/>.
iupac name: (1S,3aS,3bR,9bS,11aS)-7-ethenyl-11a-methyl-1H,2H,3H,3aH,3bH,4H,5H,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-1-ol
approved: f
ligand name: PRU-10
type: SyntheticOrganicLigand

estradiol 3-methyl ether
in ch i key: ULAADVBNYHGIBP-GFEQUFNTSA-N
in ch i: InChI=1S/C19H26O2/c1-19-10-9-15-14-6-4-13(21-2)11-12(14)3-5-16(15)17(19)7-8-18(19)20/h4,6,11,15-18,20H,3,5,7-10H2,1-2H3/t15-,16-,17+,18+,19+/m1/s1
comment: 17β-estradiol methyl ether (EDME) behaves as a direct inhibitor of the cation channel TRPML1 <Reference id=43308/>.
iupac name: (8R,9S,13S,14S,17S)-3-methoxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-ol
xref: CHEMBL116468
synonym: 17β-estradiol methyl ether
synonym: EDME
synonym: 3-Methoxyoestradiol
synonym: PRU-1
approved: f
ligand name: estradiol 3-methyl ether
type: SyntheticOrganicLigand

orotic acid
canonical SMILES: O=c1[nH]c(=O)[nH]c(c1)C(=O)O
isomeric SMILES: O=c1[nH]c(=O)[nH]c(c1)C(=O)O
in ch i key: PXQPEWDEAKTCGB-UHFFFAOYSA-N
in ch i: InChI=1S/C5H4N2O4/c8-3-1-2(4(9)10)6-5(11)7-3/h1H,(H,9,10)(H2,6,7,8,11)
comment: Orotic acid has been assigned an INN in its own right and is also a component of the INN-assigned compound orazamide.
iupac name: 2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylic acid
xref: CHEMBL1235017
synonym: orotate
approved: f
ligand name: orotic acid
type: MetaboliteLigand

donafenib
in ch i key: MLDQJTXFUGDVEO-FIBGUPNXSA-N
comment: Donafenib (CM-4307) is a deuterated derivative of the approved multikinase inhibitor <Ligand id=5711/>. Like sorafenib, it is orally active. Deuteration improves the stability of drug molecules thus extending half-life and increasing systemic exposure. This means that the effective drug dose may be shifted downward, with an associated improvement in tolerability. The medical formulation is donafenib tosylate.
xref: CHEMBL4297490
synonym: CM-4307
synonym: CM4307
synonym: Zepsun®
synonym: Sorafenib-d3
approved: f
ligand name: donafenib
type: SyntheticOrganicLigand

tetrandrine
in ch i key: WVTKBKWTSCPRNU-KYJUHHDHSA-N
in ch i: InChI=1S/C38H42N2O6/c1-39-15-13-25-20-32(42-4)34-22-28(25)29(39)17-23-7-10-27(11-8-23)45-33-19-24(9-12-31(33)41-3)18-30-36-26(14-16-40(30)2)21-35(43-5)37(44-6)38(36)46-34/h7-12,19-22,29-30H,13-18H2,1-6H3/t29-,30-/m0/s1
comment: Tetrandrine is a compound that can be extracted from the Stephania tetrandra vine, or synthesised chemically. It has been demonstrated to act as an inhibitor of multiple ion channels, including two-pore channels 1 and 2 (TPC1/2), and L- and T-type calcium channels <Reference id=28440/><Reference id=43306/>. The TPC calcium channels appear to be important for Ebola virus infection of host cells, and in vitro either ablation of TPC expression or tetrandrine-mediated inhibition of TPC channels reduces Ebola infection (IC50 55 nM) <Reference id=28440/>. SARS-CoV-2 infection (COVID-19): Tetrandrine is being studied in clinical trial for potential to treat COVID-19. The biological and pharmacological rationale for this use was reviewed in <Reference id=43305/>.
synonym: (+)-Tetrandrine
synonym: D-Tetrandrine
synonym: (S,S)-Tetrandrine
synonym: Tetrandrin
approved: t
ligand name: tetrandrine
type: SyntheticOrganicLigand

SG-094
in ch i key: BTNHPUSFPKFAPU-UHFFFAOYSA-N
in ch i: InChI=1S/C30H29NO3/c1-31-18-17-23-20-29(32-2)30(34-25-11-7-4-8-12-25)21-27(23)28(31)19-22-13-15-26(16-14-22)33-24-9-5-3-6-10-24/h3-16,20-21,28H,17-19H2,1-2H3
comment: SG-094 is an antagonist of two-pore channel (TPC) function <Reference id=43303/>. It has demonstrated anti-proliferative action in certain cancer cells at μM concentrations.
iupac name: 6-methoxy-2-methyl-7-phenoxy-1-[(4-phenoxyphenyl)methyl]-1,2,3,4-tetrahydroisoquinoline
approved: f
ligand name: SG-094
type: SyntheticOrganicLigand

SG-005
in ch i key: HZBGXMAYXSMTBE-UHFFFAOYSA-N
in ch i: InChI=1S/C32H33NO3/c1-33-18-17-27-20-31(34-2)32(36-23-26-11-7-4-8-12-26)21-29(27)30(33)19-24-13-15-28(16-14-24)35-22-25-9-5-3-6-10-25/h3-16,20-21,30H,17-19,22-23H2,1-2H3
comment: SG-005 is an antagonist of two-pore channel (TPC) function <Reference id=43303/>. It has demonstrated anti-proliferative action in certain cancer cells at μM concentrations.
iupac name: 7-(benzyloxy)-1-{[4-(benzyloxy)phenyl]methyl}-6-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline
xref: CHEMBL452763
synonym: 7,12-O,O'dibenzyl-N-methylcoclaurine
approved: f
ligand name: SG-005
type: SyntheticOrganicLigand

NS11021
in ch i key: MDKAFDIKYQMOMF-UHFFFAOYSA-N
in ch i: InChI=1S/C16H9BrF6N6S/c17-9-1-2-12(11(6-9)13-26-28-29-27-13)25-14(30)24-10-4-7(15(18,19)20)3-8(5-10)16(21,22)23/h1-6H,(H2,24,25,30)(H,26,27,28,29)
comment: NS11021 activates KCa1.1 (KCNMA1) channels <Reference id=43300/>, by modulating gating kinetics (increasing the open probability) rather than altering single channel conductance. It is used as a tool compound for investigating the physiological and pathophysiological roles of KCa1.1 channels <Reference id=43301/><Reference id=43302/>. NS11021 has more potent activating effect on KCa1.1 channels than <Ligand id=4272/>.
iupac name: 1-[3,5-bis(trifluoromethyl)phenyl]-3-[4-bromo-2-(2H-tetrazol-5-yl)phenyl]thiourea
xref: CHEMBL4303589
synonym: NS 11021
synonym: NS-11021
approved: f
ligand name: NS11021
type: SyntheticOrganicLigand

compound 40 [PMID: 34982553]
in ch i key: IIVCDBIBOGOXBU-NXDMJTDOSA-N
in ch i: InChI=1S/C49H73N13O11/c1-28(2)23-36-45(69)61-38(27-63)46(70)58-34(14-6-5-13-32(51)41(65)56-35(44(68)59-36)16-9-21-54-49(52)53)43(67)57-33(15-7-8-20-50)42(66)55-26-40(64)62-22-10-17-39(62)47(71)60-37(48(72)73)25-29-18-19-30-11-3-4-12-31(30)24-29/h3-6,11-12,18-19,24,28,32-39,63H,7-10,13-17,20-23,25-27,50-51H2,1-2H3,(H,55,66)(H,56,65)(H,57,67)(H,58,70)(H,59,68)(H,60,71)(H,61,69)(H,72,73)(H4,52,53,54)/b6-5-/t32-,33-,34-,35-,36-,37+,38-,39-/m0/s1
comment: Compound 40 is a macrocyclic analogue of the apelin receptor agonist <Ligand id=599/>, that was designed to have a reduced molecular weight whilst retaining apelin-13's cardiac effects <Reference id=43299/>. It activates Gαi1 and Gα12 signalling and β-arrestin2 recruitment but demonstrates a bias towards Gα12 signalling (~32-fold).
synonym: H2N-c[X-R-L-S-X]-K-G-P-(D-2Nal)
approved: f
ligand name: compound 40 [PMID: 34982553]
type: SyntheticOrganicLigand

compound 39 [PMID: 34982553]
in ch i key: VXVNSDXGZQXERO-NXDMJTDOSA-N
in ch i: InChI=1S/C49H73N13O11/c1-28(2)24-36-45(69)61-38(27-63)46(70)58-34(17-6-5-16-32(51)41(65)56-35(44(68)59-36)19-10-22-54-49(52)53)43(67)57-33(18-7-8-21-50)42(66)55-26-40(64)62-23-11-20-39(62)47(71)60-37(48(72)73)25-30-14-9-13-29-12-3-4-15-31(29)30/h3-6,9,12-15,28,32-39,63H,7-8,10-11,16-27,50-51H2,1-2H3,(H,55,66)(H,56,65)(H,57,67)(H,58,70)(H,59,68)(H,60,71)(H,61,69)(H,72,73)(H4,52,53,54)/b6-5-/t32-,33-,34-,35-,36-,37+,38-,39-/m0/s1
comment: Compound 39 is a macrocyclic analogue of the apelin receptor agonist <Ligand id=599/>, that was designed to have a reduced molecular weight <Reference id=43299/>. It activates Gαi1 (EC50 0.8 nM) and β-arrestin2 recruitment (EC50 31 nM) with similar potency and efficacy to apelin-13, but it does not activate Gα12 signalling. Compound 39 retains the cardiac actions of the endogenous ligand.
synonym: H2N-c[X-R-L-S-X]-K-G-P-(D-1Nal)
approved: f
ligand name: compound 39 [PMID: 34982553]
type: SyntheticOrganicLigand

IMP-1002
in ch i key: YEOAAQMCKFJWKF-UHFFFAOYSA-N
in ch i: InChI=1S/C25H30FN5O/c1-16-20(17(2)30(5)27-16)11-12-32-25-14-19(26)8-9-21(25)18-7-10-24-22(13-18)23(15-29(3)4)28-31(24)6/h7-10,13-14H,11-12,15H2,1-6H3
comment: IMP-1002 is an imipramine-based P. falciparum N-myristoyltransferase (PfNMT) inhibitor identified by structure-guided analysis <Reference id=41575/>.
iupac name: 1-(5-{4-fluoro-2-[2-(1,3,5-trimethyl-1H-pyrazol-4-yl)ethoxy]phenyl}-1-methyl-1H-indazol-3-yl)-N,N-dimethylmethanamine
approved: f
ligand name: IMP-1002
type: SyntheticOrganicLigand

TPC2-A1-P
in ch i key: INDFMVADKKBSSU-UHFFFAOYSA-N
comment: TPC2-A1-P is a selective activator of the two pore segment channel 2 TPC2 (TPCN2) <Reference id=43297/>.
iupac name: 5-[5-bromo-2-(trifluoromethoxy)phenyl]-1-(cyclohexylmethyl)-2-methyl-1H-pyrrole-3-carboxylic acid
approved: f
ligand name: TPC2-A1-P
type: SyntheticOrganicLigand

TPC2-A1-N
canonical SMILES: N#C/C(=C(/c1cc(Cl)cc(c1)Cl)/O)/C(=O)Nc1ccc(cc1)C(F)(F)F
isomeric SMILES: O/C(=C(/C#N)/C(=O)Nc1ccc(cc1)C(F)(F)F)/c1cc(Cl)cc(Cl)c1
in ch i key: FVJSEJNZNQVVDZ-CCEZHUSRSA-N
comment: TPC2-A1-N is a selective activator of the two pore segment channel 2 TPC2 (TPCN2) <Reference id=43297/>.
iupac name: (2E)-2-cyano-3-(3,5-dichlorophenyl)-3-hydroxy-N-[4-(trifluoromethyl)phenyl]prop-2-enamide
approved: f
ligand name: TPC2-A1-N
type: SyntheticOrganicLigand

ML3-SA1
canonical SMILES: Cc1cc(C)cc(c1C1=NOC2C1CCCO2)C
isomeric SMILES: Cc1cc(C)c(C2=NOC3OCCCC23)c(C)c1
in ch i key: PDQSLEUINSEJHR-UHFFFAOYSA-N
in ch i: InChI=1S/C15H19NO2/c1-9-7-10(2)13(11(3)8-9)14-12-5-4-6-17-15(12)18-16-14/h7-8,12,15H,4-6H2,1-3H3
comment: ML3-SA1 (EVP-77) is a small molecule agonist of the mucolipin TRP cation channel 3 (TRPML3; MCOLN3) <Reference id=43295/>. It has been used in a mouse model to demonstrate that TRPML3 acts as a key regulator of MMP-12 clearance by alveolar macrophages, and this identifies TRPML3 as a novel molecular target for the design of drugs to treat emphysema and chronic obstructive pulmonary disease.
iupac name: 3-(2,4,6-trimethylphenyl)-3aH,4H,5H,6H,7aH-pyrano[3,2-d][1,2]oxazole
synonym: ML3SA1
synonym: ML3 SA1
synonym: EVP-77
synonym: EVP77
approved: f
ligand name: ML3-SA1
type: SyntheticOrganicLigand

ML1-SA1
in ch i key: JSVBOFDROKCPIA-UHFFFAOYSA-N
comment: ML1-SA1 (EVP-169) is an agonist of TRPML1 ion channels <Reference id=43295/>. Structurally it is a tetrachloro analogue of <Ligand id=6386/>.
iupac name: 4,5,6,7-tetrachloro-2-[2-oxo-2-(2,2,4-trimethyl-1,2,3,4-tetrahydroquinolin-1-yl)ethyl]-2,3-dihydro-1H-isoindole-1,3-dione
synonym: ML1SA1
synonym: EVP169
synonym: EVP-169
approved: f
ligand name: ML1-SA1
type: SyntheticOrganicLigand

compound 1 [PMID: 34917254]
in ch i key: FJTQBVRKZLEDPK-UHFFFAOYSA-N
comment: This compound is a potent in vitro RET kinase inhibitor <Reference id=43291/>. It produces anti-tumour effects in RET-driven tumour xenografts.
iupac name: methyl (4-(4-amino-5-(5-amino-4-chloro-2-fluorophenyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)bicyclo[ 2.2.2]octan-1-yl)carbamate
approved: f
ligand name: compound 1 [PMID: 34917254]
type: SyntheticOrganicLigand

LY134046
canonical SMILES: Clc1ccc2c(c1Cl)CNCCC2
isomeric SMILES: Clc1ccc2c(c1Cl)CNCCC2
in ch i key: IADAQXMUWITWNG-UHFFFAOYSA-N
in ch i: InChI=1S/C10H11Cl2N/c11-9-4-3-7-2-1-5-13-6-8(7)10(9)12/h3-4,13H,1-2,5-6H2
iupac name: 8,9-dichloro-2,3,4,5-tetrahydro-1H-2-benzazepine
xref: CHEMBL38681
synonym: LY 134046
synonym: LY-134046
approved: f
ligand name: LY134046
type: SyntheticOrganicLigand

PF-06939999
in ch i key: HBGHQRGHFNTSDP-DGJRPJRTSA-N
in ch i: InChI=1S/C22H23F3N4O3/c1-10-11-3-5-29(22(11)28-9-27-10)15-7-17(20(31)19(15)30)32-16-6-13(21(24)25)18(23)12-2-4-26-8-14(12)16/h3,5-6,9,15,17,19-21,26,30-31H,2,4,7-8H2,1H3/t15-,17?,19+,20-/m1/s1
comment: PF-06939999 is an orally bioavailable, SAM-competitive PRMT5 inhibitor that was developed for ant-tumour potential <Reference id=43290/>.
iupac name: (1S,2S,5R)-3-{[6-(difluoromethyl)-5-fluoro-1,2,3,4-tetrahydroisoquinolin-8-yl]oxy}-5-{4-methyl-7H-pyrrolo[2,3-d]pyrimidin-7-yl}cyclopentane-1,2-diol
approved: f
ligand name: PF-06939999
type: SyntheticOrganicLigand

compound 5 [PMID: 34779204]
in ch i key: LQBRZKIUSVUXJP-OUAUKWLOSA-N
in ch i: InChI=1S/C14H20N4O2/c1-9-8-20-6-5-17(9)13-7-12-14(19)15-10-3-2-4-11(10)18(12)16-13/h7,9-11H,2-6,8H2,1H3,(H,15,19)/t9-,10+,11-/m1/s1
comment: This compound is an orally bioavailable and selective inhibitor of the class III phosphoinositide 3-kinase VPS34 <Reference id=43289/>, that was developed for potential to modulate autophagy, as an anti-tumour mechanism. Development was discontinued due to potential unfavourable on-target toxicity (e.g. GI tract necropsy in rats <Reference id=38578/>) arising from sustained inhibition of VPS34 kinase activity. Inhibition of VPS34 or deletion of its gene (PIK3C3) is reported to not only affect autophagy, but also alter cellular energy metabolism and disrupt membrane trafficking, phagocytosis and cytokinesis <Reference id=44039/><Reference id=44040/>. The mechanism of compound 5's interaction with VPS34 can be used to direct the search for inhibitors for other kinases which avoid VPS34 as an off-target <Reference id=44038/>.
approved: f
ligand name: compound 5 [PMID: 34779204]
type: SyntheticOrganicLigand

DS96432529
in ch i key: GOAKYBVMJUXOFY-LBPRGKRZSA-N
in ch i: InChI=1S/C18H26N4O3S/c1-2-24-8-9-25-11-12-4-3-7-22(10-12)13-5-6-21-18-14(13)15(19)16(26-18)17(20)23/h5-6,12H,2-4,7-11,19H2,1H3,(H2,20,23)/t12-/m0/s1
comment: DS96432529 was designed as a small molecule, orally active bone anabolic agent, to augment the bone mineralisation effect of osteoporosis drugs such as <Ligand id=3141/>, or parathyroid hormone (<Ligand id=1785/>) <Reference id=43288/>. It was selected for its ability to enhance alkaline phosphatase activity, which is an indicator of osteoblast differentiation. Further investigations revealed that DS96432529's pharmacodynamic effects are likely to be mediated via direct inhibition of CDK8 (kinase).
synonym: DS-96432529
synonym: compound 9o [PMID: 34742889]
approved: f
ligand name: DS96432529
type: SyntheticOrganicLigand

SY-5609
isomeric SMILES: CC1(C)CC[C@H](Nc2ncc(c(c3c[nH]c4c3ccc(C#N)c4P(=O)(C)C)n2)C(F)(F)F)CN1
in ch i key: JDJOUBVVSQDIRC-AWEZNQCLSA-N
in ch i: InChI=1S/C23H26F3N6OP/c1-22(2)8-7-14(10-30-22)31-21-29-12-17(23(24,25)26)18(32-21)16-11-28-19-15(16)6-5-13(9-27)20(19)34(3,4)33/h5-6,11-12,14,28,30H,7-8,10H2,1-4H3,(H,29,31,32)/t14-/m0/s1
comment: SY-5609 is an orally bioavailable inhibitor of CDK7 that was designed for anti-cancer potential <Reference id=43286/>. It is a derivative of <Ligand id=10467/> (SY-1365).
iupac name: 7-dimethylphosphoryl-3-[2-[[(3S)-6,6-dimethylpiperidin-3-yl]amino]-5-(trifluoromethyl)pyrimidin-4-yl]-1H-indole-6-carbonitrile
synonym: SY5609
synonym: SY-0005609
approved: f
ligand name: SY-5609
type: SyntheticOrganicLigand

GS-621763
in ch i key: RVSSLHFYCSUAHY-JQGROFRJSA-N
in ch i: InChI=1S/C24H31N5O7/c1-12(2)21(30)33-9-16-18(34-22(31)13(3)4)19(35-23(32)14(5)6)24(10-25,36-16)17-8-7-15-20(26)27-11-28-29(15)17/h7-8,11-14,16,18-19H,9H2,1-6H3,(H2,26,27,28)/t16-,18-,19-,24+/m1/s1
comment: GS-621763 is an orally bioavailable triester prodrug of <Ligand id=10715/> (GS-5734) <Reference id=43285/>. It is metabolised into the same active nucleoside triphosphate as remdesivir. Like its parent, this prodrug results in inhibition of viral RNA-dependent RNA polymerase (RdRP), and it has been evaluated against SARS-CoV-2 RdRP. GS-621763 has antiviral activity in vitro (in human primary cell systems) and has demonstrated in vivo therapeutic efficacy in mice infected with SARS-CoV-2.
iupac name: [(2R,3R,4R,5R)-5-{4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl}-5-cyano-3,4-bis[(2-methylpropanoyl)oxy]oxolan-2-yl]methyl 2-methylpropanoate
synonym: GS621763
approved: f
ligand name: GS-621763
type: SyntheticOrganicLigand

ASP2453
in ch i key: YNLGBBXDUCMNPY-UHFFFAOYSA-N
in ch i: InChI=1S/C41H49F3N6O4/c1-4-33(51)50-22-40(23-50)15-17-49(18-16-40)38-30-20-29(27-10-11-27)35(34-25(2)7-14-32-31(34)21-45-48-32)37(53-24-41(42,43)44)36(30)46-39(47-38)54-28-12-8-26(9-13-28)6-5-19-52-3/h4,7,14,20-21,26-28H,1,5-6,8-13,15-19,22-24H2,2-3H3,(H,45,48)
comment: ASP2453 is an oral, covalent inhibitor of the mutant KRASG12C protein <Reference id=43284/>. It was developed as a potential therapeutic agent for cancers that are KRASG12C positive. ASP2453 is selective for KRASG12C and has no effect on wild-type KRAS protein functions.
iupac name: 1-[7-(6-cyclopropyl-2-{[4-(3-methoxypropyl)cyclohexyl]oxy}-7-(5-methyl-1H-indazol-4-yl)-8-(2,2,2-trifluoroethoxy)quinazolin-4-yl)-2,7-diazaspiro[3.5]nonan-2-yl]prop-2-en-1-one
approved: f
ligand name: ASP2453
type: SyntheticOrganicLigand

BMS-986224
in ch i key: AGZKELPIAJYRDT-UHFFFAOYSA-N
in ch i: InChI=1S/C24H23ClN4O6/c1-4-34-12-15-19(20-16(32-2)6-5-7-17(20)33-3)22(30)21(23(31)27-15)24-29-28-18(35-24)10-14-9-8-13(25)11-26-14/h5-9,11H,4,10,12H2,1-3H3,(H2,27,30,31)
comment: BMS-986224 is an orally bioavailable small molecule apelin receptor agonist that was selected as a clinical lead with potential to treat heart failure <Reference id=43282/><Reference id=43283/>. Clinical development was discontinued at Phase 1.
iupac name: 3-[5-[(5-chloropyridin-2-yl)methyl]-1,3,4-oxadiazol-2-yl]-5-(2,6-dimethoxyphenyl)-6-(ethoxymethyl)-4-hydroxy-1H-pyridin-2-one
synonym: BMS986224
approved: f
ligand name: BMS-986224
type: SyntheticOrganicLigand

compound 14a [PMID: 34795866]
in ch i key: KSQCOKRJNWPXJJ-MRXNPFEDSA-N
in ch i: InChI=1S/C26H29ClN4O5/c1-4-5-9-21-29-24(32)22(26(34)31(21)23-19(35-2)7-6-8-20(23)36-3)25(33)30-13-12-16(15-30)18-11-10-17(27)14-28-18/h6-8,10-11,14,16,34H,4-5,9,12-13,15H2,1-3H3/t16-/m1/s1
comment: This compound is a small molecule, orally active apelin receptor agonist <Reference id=43281/>. Its pharmacodynamic effects are similar to those produced by the peptide agonist (Pyr1)apelin-13 in a rat heart failure model.
iupac name: (R)-2-butyl-5-(3-(5-chloropyridin-2-yl)pyrrolidine-1-carbonyl)-1-(2,6-dimethoxyphenyl)-6-hydroxypyrimidin-4(1H)-one
approved: f
ligand name: compound 14a [PMID: 34795866]
type: SyntheticOrganicLigand

compound 21 [PMID: 34855405]
in ch i key: BFXUALMCVABIFZ-GOSISDBHSA-N
comment: Compound 21 is a small molecule apelin receptor agonist <Reference id=43280/>.
iupac name: 5-[(3R)-3-(5-chloro-3-fluoropyridin-2-yl)pyrrolidine-1-carbonyl]-3-(2,6-diethylphenyl)-6-hydroxy-2-(1-methylpyrazol-3-yl)pyrimidin-4-one
approved: f
ligand name: compound 21 [PMID: 34855405]
type: SyntheticOrganicLigand

compound 1 [PMID: 34210738]
in ch i key: QYENXTYKACLCGO-UIWACHPISA-N
in ch i: InChI=1S/C21H29N3O5/c1-14(2)10-18(24-21(28)29-13-15-6-4-3-5-7-15)20(27)23-17(12-25)11-16-8-9-22-19(16)26/h3-7,12,14,16-18H,8-11,13H2,1-2H3,(H,22,26)(H,23,27)(H,24,28)/t16-,17-,18-/m0/s1/i13D2
comment: Compound 1 is a deuterated analogue of the Mpro inhibitor <Ligand id=10883/> <Reference id=43279/>. It has improved potency compared to GC-376 in enzyme activity and cell infection assays, and is non-cytotoxic in vitro.
iupac name: Phenylmethyl-d2((S)-4-methyl-1-oxo-1-(((S)-1-oxo-3-((S)-2-oxopyrrolidin-3-yl)propan-2-yl)amino)pentan-2-yl)carbamate
approved: f
ligand name: compound 1 [PMID: 34210738]
type: SyntheticOrganicLigand

compound 15c [PMID: 34865476]
in ch i key: DVWOYOSIEJRHKW-UIRZNSHLSA-M
comment: Compound 15c is one of the most potent SARS-CoV-2 Mpro inhibitors, from an extensive series with IC50 values around 200-400 nM <Reference id=43278/>. The chemical structure shown here was rendered using the SMILES provided in the primary reference. 15c was crystalised in complex with SARS-CoV-2 Mpro and the structural data is available from the PDB (ID 7T4B).
iupac name: (4,4-difluorocyclohexyl)(phenyl)methyl N-[(1S)-1-{[(2S)-1-hydroxy-3-[(3S)-2-oxopyrrolidin-3-yl]-1-[(sodiooxy)sulfonyl]propan-2-yl]carbamoyl}-3-methylbutyl]carbamate
approved: f
ligand name: compound 15c [PMID: 34865476]
type: SyntheticOrganicLigand

compound 21k [PMID: 34985886]
in ch i key: UVLOISNMRLZTPF-UHFFFAOYSA-N
in ch i: InChI=1S/C23H18FN3O2/c24-19-4-1-15(2-5-19)14-27-9-10-29-21-12-16(3-6-20(21)23(27)28)18-11-17-7-8-25-22(17)26-13-18/h1-8,11-13H,9-10,14H2,(H,25,26)
comment: Compound 21k was designed as an inhibitor of TRAF2 and NCK interacting kinase (TNIK) <Reference id=43275/>. Inhibition of TNIK is proposed as a mechanism to combat dysregulated Wnt/β-catenin signalling in colorectal cancer.
iupac name: 4-(4-Fluorobenzyl)-8-(1H-pyrrolo[2,3-b]pyridin-5-yl)-3,4-dihydrobenzo[f][1,4]oxazepin-5(2H)-one
approved: f
ligand name: compound 21k [PMID: 34985886]
type: SyntheticOrganicLigand

compound 10 [PMID: 34989568]
in ch i key: RTKBIHCZDFXHLC-UHFFFAOYSA-N
in ch i: InChI=1S/C25H23F3N4O2/c1-3-4-9-34-23-13-21(20-7-5-6-8-22(20)31-23)24(33)30-18-10-17(25(26,27)28)11-19(12-18)32-14-16(2)29-15-32/h5-8,10-15H,3-4,9H2,1-2H3,(H,30,33)
comment: This compound was desigend as an experimental probe for studying the function of the nuclear receptor TLX (NR2E1) <Reference id=43274/>. TLX is a molecular target with potential application in neurodegenerative diseases.
iupac name: 2-Butyloxy-N-(3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl)quinoline-4-carboxamide
approved: f
ligand name: compound 10 [PMID: 34989568]
type: SyntheticOrganicLigand

levoketoconazole
in ch i key: XMAYWYJOQHXEEK-ZEQKJWHPSA-N
comment: Levoketoconazole is the pure (2S,4R) enantiomer of the approved drug <Ligand id=2568/>. Like ketoconazole, levoketoconazole is orally available. It is a more potent inhibitor of glucocorticoid synthesis than the enantiomerically mixed ketoconazole formulation. Levoketoconazole reduces cortisol biosynthesis by inhibiting three key cytochrome P450 enzymes of the glucocorticoid synthesis pathway; 11β-hydroxylase (CYP11B1), 17α-hydroxylase/17,20-lyase (CYP17A1) and steroid 21-hydroxylase (CYP21A2).
iupac name: 1-[4-[4-[[(2S,4R)-2-(2,4-dichlorophenyl)-2-(imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]piperazin-1-yl]ethanone
xref: CHEMBL295698
synonym: COR-003
synonym: COR003
synonym: Recorlev®
synonym: (2S,4R)-ketoconazole
approved: t
ligand name: levoketoconazole
type: SyntheticOrganicLigand

enarodustat
in ch i key: FJYRBJKWDXVHHO-UHFFFAOYSA-N
in ch i: InChI=1S/C17H16N4O4/c22-13-8-12(7-6-11-4-2-1-3-5-11)21-16(19-10-20-21)15(13)17(25)18-9-14(23)24/h1-5,8,10H,6-7,9H2,(H,18,25)(H,19,20)(H,23,24)
comment: Enarodustat (JTZ-951) is an orally active inhibitor of hypoxia-inducible factor prolyl hydroxylase (HIF-PH) enzyme activity <Reference id=43263/>. Inhibition of prolyl hydroxylation of HIF transcription factors is used as an alternative to erythropoiesis-stimulating agents (epoetin, darbepoetin) for the treatment of anaemia resulting from chronic kidnery disease <Reference id=43264/><Reference id=43266/>.
xref: CHEMBL4297619
synonym: JTZ-951
synonym: JTZ951
synonym: compound 14 [PMID: 29259755]
synonym: Enaroy®
approved: t
ligand name: enarodustat
type: SyntheticOrganicLigand

ITH15004
canonical SMILES: Clc1ccc(c(c1)Cl)C(=O)Cn1cnc2c1ncnc2Cl
isomeric SMILES: Clc1c2ncn(c2ncn1)CC(=O)c1c(cc(cc1)Cl)Cl
in ch i key: NLRGSGVPLHCTPK-UHFFFAOYSA-N
in ch i: InChI=1S/C13H7Cl3N4O/c14-7-1-2-8(9(15)3-7)10(21)4-20-6-19-11-12(16)17-5-18-13(11)20/h1-3,5-6H,4H2
comment: ITH15004 is a non-nucleotide purine derivative that acts as an antagonist of ATP-gated P2X7 ion channel activity <Reference id=43249/>. It can cross the blood-brain barrier, and has been used to investigate the potential of P2X7 antagonism to ameliorate neuroinflammation.
iupac name: 2-(6-chloro-9H-purin-9-yl)-1-(2,4-dichlorophenyl)-1-ethanone
synonym: compound 6 [PMID: 33560845]
synonym: ITH-15004
approved: f
ligand name: ITH15004
type: SyntheticOrganicLigand

MMV897698
in ch i key: AVBCIJLYABLIRW-UHFFFAOYSA-N
in ch i: InChI=1S/C20H16F2N4O2/c21-20(22)28-16-8-6-15(7-9-16)19-25-24-17-12-23-13-18(26(17)19)27-11-10-14-4-2-1-3-5-14/h1-9,12-13,20H,10-11H2
comment: MMV897698 is an antimalarial compound identified during optimization of Open Source Malaria (OSM) Series 4 <Reference id=43241/>. The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
iupac name: 3-[4-(difluoromethoxy)phenyl]-5-(2-phenylethoxy)-[1,2,4]triazolo[4,3-a]pyrazine
synonym: compound 6 [PMID: 32678591]
synonym: OSM-S-369
approved: f
ligand name: MMV897698
type: SyntheticOrganicLigand

MMV1803022
in ch i key: YXNHLRADFLNVIV-UHFFFAOYSA-N
in ch i: InChI=1S/C23H22F2N4O3/c1-23(2,3)32-16-7-4-14(5-8-16)22-28-27-20-11-26-12-21(29(20)22)31-13-19(30)15-6-9-17(24)18(25)10-15/h4-12,19,30H,13H2,1-3H3
comment: MMV1803022 is a novel antimalarial compound identified through an Open Source Malaria (OSM) consortium predictive model competition <Reference id=43240/>. The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
iupac name: 1-(3,4-difluorophenyl)-2-[[3-[4-[(2-methylpropan-2-yl)oxy]phenyl]-[1,2,4]triazolo[4,3-a]pyrazin-5-yl]oxy]ethanol
approved: f
ligand name: MMV1803022
type: SyntheticOrganicLigand

AIM-1290
canonical SMILES: O=C(Nc1cnc(s1)c1ccc(cc1F)F)CCCN1CCOCCC1
in ch i key: RPGKIKHEBZDURC-UHFFFAOYSA-N
comment: AIM-1290 is the lead compound from a novel series of thiazole-containing amides that are potent and selective inhibitors of P. falciparum bifunctional farnesyl/geranylgeranyl diphosphate synthase (PfFPPS/GGPPS) <Reference id=43031/>. The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
iupac name: N-[2-(2,4-Difluorophenyl)-1,3-thiazol-5-yl]-4-(1,4-oxazepan-4-yl)butanamide trifluoroacetate
approved: f
ligand name: AIM-1290
type: SyntheticOrganicLigand

NCATS-SM3710
in ch i key: VPSFQPBONOUNSO-UHFFFAOYSA-N
in ch i: InChI=1S/C28H20ClN3O2/c29-21-7-1-17(2-8-21)19-5-13-25-24(15-19)27-20(16-30-25)6-14-26(33)32(27)23-11-3-18(4-12-23)28(34)31-22-9-10-22/h1-8,11-16,22H,9-10H2,(H,31,34)
comment: NCATS-SM3710 is a <Ligand id=8839/> derivative, with potent antimalarial activity <Reference id=43238/>.
iupac name: 4-[9-(4-chlorophenyl)-2-oxobenzo[h][1,6]naphthyridin-1-yl]-N-cyclopropylbenzamide
approved: f
ligand name: NCATS-SM3710
type: SyntheticOrganicLigand

VU0134992
in ch i key: OTTDLWFVHQYRDA-UHFFFAOYSA-N
in ch i: InChI=1S/C20H31BrN2O2/c1-13(2)14-7-8-17(16(21)9-14)25-12-18(24)22-15-10-19(3,4)23-20(5,6)11-15/h7-9,13,15,23H,10-12H2,1-6H3,(H,22,24)
comment: VU 0134992 is a potassium channel blocker, with modest selectivit for Kir4.1 (KCNJ10) channels <Reference id=43236/>. It is active in vitro, increasing urine output and urinary Na+ and K+ excretion in volume-loaded rats.
iupac name: 2-(2-bromo-4-isopropylphenoxy)-N-(2,2,6,6-tetramethylpiperidin-4-yl)acetamide
xref: CHEMBL1871911
synonym: VU 0134992
synonym: VU-0134992
synonym: VU992
synonym: VU-992
approved: f
ligand name: VU0134992
type: SyntheticOrganicLigand

alpha-D-pentagalloylglucose
in ch i key: QJYNZEYHSMRWBK-LOMPCTGFSA-N
in ch i: InChI=1S/C41H32O26/c42-17-1-12(2-18(43)28(17)52)36(57)62-11-27-33(64-37(58)13-3-19(44)29(53)20(45)4-13)34(65-38(59)14-5-21(46)30(54)22(47)6-14)35(66-39(60)15-7-23(48)31(55)24(49)8-15)41(63-27)67-40(61)16-9-25(50)32(56)26(51)10-16/h1-10,27,33-35,41-56H,11H2/t27-,33-,34-,35+,41-/m0/s1
comment: α-PGG is a minor component of tannic acid; β-PGG being the predominant anomer produced in plants.
iupac name: [(2S,3S,4S,5R,6S)-3,4,5,6-tetrakis(3,4,5-trihydroxybenzoyloxy)oxan-2-yl]methyl 3,4,5-trihydroxybenzoate
synonym: aPGG
synonym: αPGG
synonym: 1,2,3,4,6-penta-O-galloyl-a-D-glucopyranose
synonym: α-PGG
approved: f
ligand name: alpha-D-pentagalloylglucose
type: SyntheticOrganicLigand

NT23
in ch i key: IMTBFONQRNCXSE-UHFFFAOYSA-N
comment: NT23 is a small molecule that can displace insulin from its binding site on the insulin receptor <Reference id=43232/>. It shows concentration-dependent binding to the receptor in vitro.
iupac name: 1-[4-(difluoromethoxy)phenyl]-2-[[5-(2-fluoroanilino)-1,3,4-thiadiazol-2-yl]sulfanyl]ethanone
xref: CHEMBL606690
synonym: NT-23
synonym: compound 1 [PMID: 20158183]
approved: f
ligand name: NT23
type: SyntheticOrganicLigand

levonantradol
in ch i key: FFVXQGMUHIJQAO-BFKQJKLPSA-N
in ch i: InChI=1S/C27H35NO4/c1-17(8-7-11-20-9-5-4-6-10-20)31-22-15-25-27(26(16-22)32-19(3)29)24-14-21(30)12-13-23(24)18(2)28-25/h4-6,9-10,15-18,21,23-24,28,30H,7-8,11-14H2,1-3H3/t17-,18+,21-,23+,24-/m1/s1
comment: Levonantradol is a synthetic cannabinoid analogue <Reference id=43229/><Reference id=34096/>.
xref: CHEMBL2111116
synonym: (-)-nantradol
synonym: CP 50,556-1
approved: f
ligand name: levonantradol
type: SyntheticOrganicLigand

URB937
in ch i key: CMEQHOXCIGFZNJ-UHFFFAOYSA-N
in ch i: InChI=1S/C20H22N2O4/c21-19(24)14-6-4-5-13(11-14)17-12-16(9-10-18(17)23)26-20(25)22-15-7-2-1-3-8-15/h4-6,9-12,15,23H,1-3,7-8H2,(H2,21,24)(H,22,25)
comment: URB937 is a peripherally restricted inhibitor of fatty-acid amide hydrolase (FAAH) <Reference id=43228/>.
iupac name: [3-(3-carbamoylphenyl)-4-hydroxyphenyl] N-cyclohexylcarbamate
xref: CHEMBL2402927
synonym: URB-937
approved: f
ligand name: URB937
type: SyntheticOrganicLigand

ABD-1970
in ch i key: CXSFVTMRWPSLGO-UHFFFAOYSA-N
comment: ABD-1970 is a potent and selective inhibitor of monoacylglycerol lipase (MAGL) <Reference id=43227/>. It is active in vitro and in vivo.
iupac name: 1,1,1,3,3,3-hexafluoropropan-2-yl 4-[[4-chloro-2-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)phenyl]methyl]piperazine-1-carboxylate
xref: CHEMBL4517565
synonym: ABD1970
approved: f
ligand name: ABD-1970
type: SyntheticOrganicLigand

SA-57
canonical SMILES: CNC(=O)COC(=O)N1CCC(CC1)CCc1ccc(cc1)Cl
isomeric SMILES: Clc1ccc(cc1)CCC1CCN(C(=O)OCC(=O)NC)CC1
in ch i key: JFSSVCSHPDLFCM-UHFFFAOYSA-N
in ch i: InChI=1S/C17H23ClN2O3/c1-19-16(21)12-23-17(22)20-10-8-14(9-11-20)3-2-13-4-6-15(18)7-5-13/h4-7,14H,2-3,8-12H2,1H3,(H,19,21)
comment: SA-57 is an inhibitor of fatty acid amide hydrolase (FAAH) <Reference id=43226/>. Off-target inhibition of monoacylglycerol lipase (MAGL) and αβ-Hydrolase 6 (ABHD6) can occur.
iupac name: [2-(methylamino)-2-oxoethyl] 4-[2-(4-chlorophenyl)ethyl]piperidine-1-carboxylate
xref: CHEMBL457918
synonym: SA57
approved: f
ligand name: SA-57
type: SyntheticOrganicLigand

iboxamycin
in ch i key: JPCLUJPDWMBCAA-ALYUFWCISA-N
comment: Iboxamycin (OPP-3) is an orally bioavailable, synthetic antibacterial compound <Reference id=43166/>. Structurally, IBX is built on a oxepanoproline scaffold that is linked to the aminooctose residue of <Ligand id=10607/>. X-ray crystallography shows that IBX binds to the large ribosomal subunit in the bacteria (more effectively than clindamycin) and disrupts translation initiation. Iboxamycin is a novel broad-spectrum agent that is active against Gram-positive and Gram-negative bacteria including ESKAPE pathogens that express resistance-conferring Erm and Cfr ribosomal RNA methyltransferase enzymes.
iupac name: (4S,5aS,8S,8aR)-N-[(1S,2S)-2-chloro-1-[(2S,4R,5R)-3,4,5-trihydroxy-6-(methylsulfanyl)oxan-2-yl]propyl]-4-(2-methylpropyl)-octahydro-2H-oxepino[2,3-c]pyrrole-8-carboxamide
synonym: OPP-3
synonym: IBX
approved: f
ligand name: iboxamycin
type: SyntheticOrganicLigand

[D-Lys3]-GHRP-6
in ch i key: MGSNWNLPMHXGDD-DFWOJPNQSA-N
in ch i: InChI=1S/C49H63N13O6/c50-20-10-8-18-39(44(53)63)58-47(66)41(22-30-12-2-1-3-13-30)61-49(68)43(24-32-27-56-38-17-7-5-15-35(32)38)62-46(65)40(19-9-11-21-51)59-48(67)42(23-31-26-55-37-16-6-4-14-34(31)37)60-45(64)36(52)25-33-28-54-29-57-33/h1-7,12-17,26-29,36,39-43,55-56H,8-11,18-25,50-52H2,(H2,53,63)(H,54,57)(H,58,66)(H,59,67)(H,60,64)(H,61,68)(H,62,65)/t36-,39-,40+,41+,42+,43-/m0/s1
comment: [D-Lys3]-GHRP-6 is a peptidic ghrelin receptor antagonist <Reference id=43222/><Reference id=43223/>.
iupac name: (2S)-6-amino-2-[[(2R)-2-[[(2S)-2-[[(2R)-6-amino-2-[[(2R)-2-[[(2S)-2-amino-3-(1H-imidazol-5-yl)propanoyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]hexanoyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]-3-phenylpropanoyl]amino]hexanamide
synonym: [D-Lys] GHRP-6
approved: f
ligand name: [D-Lys3]-GHRP-6
type: PeptideLigand

idremcinal
in ch i key: FPBKIOZMKHHNLL-CBUZSSJJSA-N
in ch i: InChI=1S/C39H69NO12/c1-15-27-39(12,45)32(42)22(6)30-20(4)17-38(11,52-30)34(51-36-29(41)26(16-21(5)47-36)40(13)19(2)3)23(7)31(24(8)35(44)49-27)50-28-18-37(10,46-14)33(43)25(9)48-28/h19,21-29,31-34,36,41-43,45H,15-18H2,1-14H3/t21-,22+,23+,24-,25+,26+,27-,28+,29-,31+,32-,33+,34-,36+,37-,38-,39-/m1/s1
comment: Idremcinal (EM-574) is an erythromycin derivative that acts as a motilin receptor agonist <Reference id=43220/>. It is orally bioactive <Reference id=43221/>.
iupac name: (2R,3R,4S,5R,8R,9S,10S,11R,12R)-5-ethyl-3,4-dihydroxy-9-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-11-[(2S,3R,4S,6R)-3-hydroxy-6-methyl-4-[methyl(propan-2-yl)amino]oxan-2-yl]oxy-2,4,8,10,12,14-hexamethyl-6,15-dioxabicyclo[10.2.1]pentadec-1(14)-en-7-one
xref: CHEMBL2103968
synonym: EM574
synonym: EM-574
approved: f
ligand name: idremcinal
type: SyntheticOrganicLigand

XMU-MP-1
in ch i key: YRDHKIFCGOZTGD-UHFFFAOYSA-N
in ch i: InChI=1S/C17H16N6O3S2/c1-22-12-7-8-27-14(12)16(24)23(2)13-9-19-17(21-15(13)22)20-10-3-5-11(6-4-10)28(18,25)26/h3-9H,1-2H3,(H2,18,25,26)(H,19,20,21)
comment: XMU-MP-1 is a small molecule inhibitor of the STE20 family kinases serine/threonine kinases MST1 (STK4) and MST2 (STK3) <Reference id=43219/>. It has off-target activty against ULK1/2 and Aurora kinases which needs to be considered when it is used as a tool compound.
xref: CHEMBL4554938
approved: f
ligand name: XMU-MP-1
type: SyntheticOrganicLigand

SBP-3264
in ch i key: AYRVYPOFYQSRNH-UHFFFAOYSA-N
in ch i: InChI=1S/C19H20ClN5O/c1-12(26)24-15-5-7-25(8-6-15)19-17-16(10-21-18(17)22-11-23-19)13-3-2-4-14(20)9-13/h2-4,9-11,15H,5-8H2,1H3,(H,24,26)(H,21,22,23)
comment: SBP-3264 is an inhibitor of the STE20 family serine/threonine kinases STK3 (MST2) and STK4 (MST1) <Reference id=43215/>. STK3/4 activity initiates modulation of downstream Hippo pathway components which culminates in negative regulation of the major Hippo pathway transcriptional coactivators, Yes-associated protein 1 (YAP1) and transcriptional coactivator with PDZ-binding motif (TAZ; WWTR1). The Hippo pathway regulates cell proliferation, differentiation, and apoptosis. STK3 and STK4 have been identified as a potential targets for antileukemia therapy <Reference id=43216/><Reference id=43217/><Reference id=43218/>.
synonym: SBP 3264
synonym: SBP3264
synonym: compound 20 [PMID: 34807584]
approved: f
ligand name: SBP-3264
type: SyntheticOrganicLigand

CP-424,174
in ch i key: YRSBLSHMKVQWHP-UHFFFAOYSA-N
comment: CP-424,174 is a diarylsulfonylurea compound that inhibits conversion of pro-IL-1β to its active soluble form <Reference id=43214/>. It can be used to investigate the effects of controlling IL-1β production in inflammatory diseases. It has an additinal hydroxyl group compared to <Ligand id=11809/>. The direct NLRP3 inhibitor <Ligand id=8228/> has a related structure.
iupac name: 3-[4-chloro-2,6-bis(propan-2-yl)phenyl]-1-[3-(2-hydroxypropan-2-yl)benzenesulfonyl]urea
xref: CHEMBL3781583
synonym: CP-424174
approved: f
ligand name: CP-424,174
type: SyntheticOrganicLigand

CP-412,245
in ch i key: ZKEBNWAADHAYQJ-UHFFFAOYSA-N
comment: CP-412,245 is a diarylsulfonylurea compound that inhibits conversion of pro-IL-1β to its active soluble form <Reference id=43214/>. It can be used to investigate the effects of controlling IL-1β production in inflammatory diseases. The direct NLRP3 inhibitor <Ligand id=8228/> has a related structure.
iupac name: 3-[4-chloro-2,6-bis(propan-2-yl)phenyl]-1-[3-(propan-2-yl)benzenesulfonyl]urea
approved: f
ligand name: CP-412,245
type: SyntheticOrganicLigand

JX21108
canonical SMILES: N#Cc1ccc2c(c1)c(C[NH+]1CCC3(C1)CCN(C3)c1ncc(cn1)C(=O)NO)cn2C
in ch i key: XYBGCCKUMXSCIP-UHFFFAOYSA-O
in ch i: InChI=1S/C23H25N7O2/c1-28-12-18(19-8-16(9-24)2-3-20(19)28)13-29-6-4-23(14-29)5-7-30(15-23)22-25-10-17(11-26-22)21(31)27-32/h2-3,8,10-12,32H,4-7,13-15H2,1H3,(H,27,31)/p+1
comment: JX21108 is a selective inhibitor of P. falciparum histone deacetylase 1 (PfHDAC1) that was developed from chemical optimization of <Ligand id=7503/> <Reference id=43239/>.
iupac name: 2-[7-[(5-cyano-1-methylindol-3-yl)methyl]-2-aza-7-azoniaspiro[4.4]nonan-2-yl]-N-hydroxypyrimidine-5-carboxamide
approved: f
ligand name: JX21108
type: SyntheticOrganicLigand

TNNI3K degrader
in ch i key: OGZQGEDLXOIYFN-UHFFFAOYSA-N
in ch i: InChI=1S/C43H53N11O6S/c1-44-61(58,59)35-13-15-39(49(2)3)38(30-35)47-41-36-14-12-34(29-37(36)45-31-46-41)60-28-6-18-51-22-26-53(27-23-51)43(57)52-24-20-50(21-25-52)17-5-4-7-32-8-10-33(11-9-32)54-19-16-40(55)48-42(54)56/h8-15,29-31,44H,5-6,16-28H2,1-3H3,(H,45,46,47)(H,48,55,56)
comment: This compound is a bifunctional degrader of the cardiac-specific kinase TNNI3K protein, that is claimed in patent WO2021053495A1 <Reference id=43799/>. It's kinase binding domain is derived from the quinazoline TNNI3K inhibitor GSK114 <Reference id=43201/>, and it contains a cereblon binding ligand to promote association with the protein-degrading E3 ubiquitin ligase complex.
iupac name: 4-(dimethylamino)-3-[[7-[3-[4-[4-[4-[4-(2,4-dioxo-1,3-diazinan-1-yl)phenyl]but-3-ynyl]piperazine-1-carbonyl]piperazin-1-yl]propoxy]quinazolin-4-yl]amino]-N-methylbenzenesulfonamide
synonym: compound 21 [WO2021053495A1]
approved: f
ligand name: TNNI3K degrader
type: SyntheticOrganicLigand

GSK329
in ch i key: QOQADIYOLOHRAW-UHFFFAOYSA-N
comment: GSK329 is a small molecule inhibitor of cardiac-specific kinase TNNI3K (TNNI3 interacting kinase) <Reference id=43200/>. It was derived from the scaffold of the multi-kinase inhibitor <Ligand id=5711/> (IC50 100nM vs. TNNI3K). GSK329 is suitable as an in vivo tool to assess inhibition of TNNI3K as a novel therapeutic strategy for the treatment of cardiovascular diseases.
iupac name: 1-[3,5-dichloro-4-[6-(methylamino)pyrimidin-4-yl]oxyphenyl]-3-[3-(trifluoromethyl)phenyl]urea
synonym: GSK-329
synonym: compound 47 [PMID: 34699203]
approved: f
ligand name: GSK329
type: SyntheticOrganicLigand

hGLP-2(3-33,M10Y)
in ch i key: YVPAJDRBTJWURG-YXFFYCBWSA-N
comment: The methionine in position 10 of human GLP-2(3-33) has been substituted with tyrosine (M10Y) to enable oxidative iodination of the peptide and generation of a [125I]-labelled radioligand that is useful for studying basic GLP-2R pharmacology <Reference id=43796/>.
approved: f
ligand name: hGLP-2(3-33,M10Y)
type: PeptideLigand

hGLP-2(1-33,M10Y)
in ch i key: BONVCUWVEHTDCR-NTNVLEAHSA-N
comment: The methionine in position 10 of human GLP-2(1-33) has been substituted with tyrosine (M10Y) to enable oxidative iodination of the peptide and generation of a [125I]-labelled radioligand that is useful for studying basic GLP-2R pharmacology <Reference id=43796/>.
approved: f
ligand name: hGLP-2(1-33,M10Y)
type: PeptideLigand

OCT2013
canonical SMILES: CC[N+](CC(=O)Nc1c(C)cccc1C)(CC)[O-]
isomeric SMILES: Cc1c(NC(=O)C[N+](CC)(CC)[O-])c(ccc1)C
in ch i key: YDVXPJXUHRROBA-UHFFFAOYSA-N
in ch i: InChI=1S/C14H22N2O2/c1-5-16(18,6-2)10-13(17)15-14-11(3)8-7-9-12(14)4/h7-9H,5-6,10H2,1-4H3,(H,15,17)
comment: OCT2013 is an aliphatic amine N-oxide that is converted to lidocaine in vivo <Reference id=43797/>. This conversion can occur in the reducing environment of the ischaemic myocardium, an effect that may offer an alternative to lidocaine to produce conduction block during ventricular tachyarrhythmias.
iupac name: 2-(2,6-dimethylanilino)-N,N-diethyl-2-oxoethanamine oxide
synonym: lidocaine N-oxide
approved: f
ligand name: OCT2013
type: SyntheticOrganicLigand

AZD2906
in ch i key: YDRQCGICZKAGCQ-LMKMVOKYSA-N
in ch i: InChI=1S/C26H25FN4O3/c1-16(30-26(32)17-3-4-17)25(18-5-12-24(33-2)28-14-18)34-22-10-11-23-19(13-22)15-29-31(23)21-8-6-20(27)7-9-21/h5-17,25H,3-4H2,1-2H3,(H,30,32)/t16-,25-/m0/s1
comment: AZD2906 is a nonsteroidal glucocorticoid receptor (GR) agonist <Reference id=43148/>. It was the structural starting point for the development of <Ligand id=9812/> <Reference id=34289/>.
iupac name: N-[(1R,2S)-1-[1-(4-fluorophenyl)indazol-5-yl]oxy-1-(6-methoxypyridin-3-yl)propan-2-yl]cyclopropanecarboxamide
xref: CHEMBL3937635
synonym: AZD-2906
synonym: compound 4 [PMID: 29424542]
approved: f
ligand name: AZD2906
type: SyntheticOrganicLigand

compound 10 [PMID: 34704759]
in ch i key: RRGOOOPOTXFKKZ-UNVBUFFDSA-N
comment: Compound 10 is a long-acting prodrug of the TGFβR inhibitor BMS-986260 <Reference id=43192/>. It contains a matriptase peptide substrate domain, that is cleaved by the protease selectively in the tumour microenvironment. Compound 10 is sufficiently soluble to allow parenteral administration. We generated the chemical structure shown here from the SMILES provided in the disclosure <Reference id=43192/>. This prodrug approach is proposed to limit exposure of non-tumour tissue to the active parent molecule.
approved: f
ligand name: compound 10 [PMID: 34704759]
type: SyntheticOrganicLigand

reldesemtiv
in ch i key: MQXWPWOCXGARRK-UHFFFAOYSA-N
in ch i: InChI=1S/C19H18F2N6O/c20-13-6-19(7-13,16-15(21)2-1-4-23-16)11-26-18-24-8-14(9-25-18)27-5-3-12(10-27)17(22)28/h1-5,8-10,13H,6-7,11H2,(H2,22,28)(H,24,25,26)
comment: Reldesemtiv (CK-2127107) is a second generation fast skeletal muscle troponin activator <Reference id=43191/>, that was designed to improve upon <Ligand id=8280/>. Reldesemtiv slows the rate of calcium release from the troponin complex, and sensitises the sarcomere to calcium which leads to increased contractility in fast skeletal muscle fibres. Like tirasemtiv, reldesemtiv was proposed to offer a therapeutic option for debilitating muscle weakness/muscle fatigue in diseases such as spinal muscular atrophy (SMA) and amyotrophic lateral sclerosis (ALS).
iupac name: 1-[2-[[3-fluoro-1-(3-fluoropyridin-2-yl)cyclobutyl]methylamino]pyrimidin-5-yl]pyrrole-3-carboxamide
xref: CHEMBL4297600
synonym: CK-2127107
synonym: CK2127107
synonym: CK-107
approved: f
ligand name: reldesemtiv
type: SyntheticOrganicLigand

CP-628006
in ch i key: KCAXPRFNWUOBNC-RDAHNBDFSA-N
in ch i: InChI=1S/C32H35F3N2O2/c1-22-26(8-5-17-36-22)21-37-29(38)25-10-12-28-24(18-25)9-11-27-20-30(39,14-16-32(33,34)35)13-15-31(27,28)19-23-6-3-2-4-7-23/h2-8,10,12,17-18,27,39H,9,11,13-16,19-21H2,1H3,(H,37,38)/t27-,30+,31+/m1/s1
comment: CP-628006 is a CFTR potentiator <Reference id=43186/>. It restores function to the cystic fibrosis CFTR gating variant G551D by increasing the frequency and duration of channel openings.
iupac name: (4bS,7S,8aR)-4b-benzyl-7-hydroxy-N-[(2-methylpyridin-3-yl)methyl]-7-(3,3,3-trifluoropropyl)-5,6,8,8a,9,10-hexahydrophenanthrene-2-carboxamide
xref: CHEMBL3647439
synonym: CP628006
approved: f
ligand name: CP-628006
type: SyntheticOrganicLigand

SJ995973
in ch i key: DBLAYWMXROFYQV-CPRJBALCSA-N
comment: SJ995973 is a novel proteolysis-targeting chimera (PROTAC) molecule that targets bromodomain and extra-terminal (BET) proteins for proteasome-mediated degradation <Reference id=43185/>. The cereblon binding warhead contains a phenyl glutarimide group that improves chemical resistance to hydrolysis, thereby improving PROTAC efficacy. The BET binding component is based on the BRD4 inhibitor <Ligand id=7511/>, that is also utilised in the PROTAC <Ligand id=10534/>.
synonym: PG PROTAC 4c
synonym: compound 4c [PMID: 34614283]
approved: f
ligand name: SJ995973
type: SyntheticOrganicLigand

BMS-986278
in ch i key: UEUNDURNLYLSNB-HOTGVXAUSA-N
in ch i: InChI=1S/C22H31N5O5/c1-5-11-26(3)22(30)31-13-18-20(24-25-27(18)4)17-9-10-19(14(2)23-17)32-16-8-6-7-15(12-16)21(28)29/h9-10,15-16H,5-8,11-13H2,1-4H3,(H,28,29)/t15-,16-/m0/s1
comment: BMS-986278 a lysophosphatidic acid receptor 1 (LPA1) antagonist <Reference id=43184/>. It was advanced into clinical trials to determine its efficacy as a treatment for fibrotic lung conditions.
iupac name: (1S,3S)-3-[2-methyl-6-[1-methyl-5-[[methyl(propyl)carbamoyl]oxymethyl]triazol-4-yl]pyridin-3-yl]oxycyclohexane-1-carboxylic acid
synonym: compound 33 [PMID: 34709814]
synonym: BMS986278
approved: f
ligand name: BMS-986278
type: SyntheticOrganicLigand

FNDR-20123
in ch i key: MTAWGBVDXCFYOF-UHFFFAOYSA-N
in ch i: InChI=1S/C21H23N5O2/c27-21(23-28)19-9-5-17(6-10-19)14-26-15-20(22-24-26)18-7-3-16(4-8-18)13-25-11-1-2-12-25/h3-10,15,28H,1-2,11-14H2,(H,23,27)
comment: FNDR-20123 is the most potent antimalarial compound identified from a HDAC inhibitor library screening study <Reference id=43183/>.
iupac name: N-hydroxy-4-[[4-[4-(pyrrolidin-1-ylmethyl)phenyl]triazol-1-yl]methyl]benzamide
xref: CHEMBL4090165
approved: f
ligand name: FNDR-20123
type: SyntheticOrganicLigand

MMV693183
in ch i key: PRPWMPIRTLCTSC-SDBXPKJASA-N
in ch i: InChI=1S/C16H21F3N2O4/c1-8(6-20-15(25)13(23)16(2,3)7-22)21-14(24)9-4-11(18)12(19)5-10(9)17/h4-5,8,13,22-23H,6-7H2,1-3H3,(H,20,25)(H,21,24)/t8-,13-/m0/s1
comment: MMV693183 is an optimized preclinical candidate from the pantothenamide class of antimalarial compounds <Reference id=43182/>.
iupac name: N-[(2S)-1-[[(2R)-2,4-dihydroxy-3,3-dimethylbutanoyl]amino]propan-2-yl]-2,4,5-trifluorobenzamide
approved: f
ligand name: MMV693183
type: SyntheticOrganicLigand

BAY-297
canonical SMILES: CC[C@H](C(=O)N)Nc1c(C#N)c(nc2c1ccnc2)c1ccc(cc1)c1cccc(c1F)Cl
isomeric SMILES: Clc1c(c(ccc1)c1ccc(cc1)c1nc2cnccc2c(c1C#N)N[C@@H](C(=O)N)CC)F
in ch i key: LACMSNCHWBQXEK-HXUWFJFHSA-N
in ch i: InChI=1S/C25H19ClFN5O/c1-2-20(25(29)33)31-24-17-10-11-30-13-21(17)32-23(18(24)12-28)15-8-6-14(7-9-15)16-4-3-5-19(26)22(16)27/h3-11,13,20H,2H2,1H3,(H2,29,33)(H,31,32)/t20-/m1/s1
comment: BAY-297 is an ATP-competitive inhibitor of the lipid modifying kinase phosphatidylinositol-5-phosphate 4-kinase type 2 alpha (PIP4K2A) <Reference id=43178/>. It was designed to aid exploration of the role(s) played by PIP4K2A and -B in pathophysiological conditions such as cancer. BAY-297 and <Ligand id=11793/> were reported from the same study that used high-throughput screening and SAR optimisation to identify small molecule PIP4K2A inhibitors.
iupac name: (2R)-2-[[2-[4-(3-chloro-2-fluorophenyl)phenyl]-3-cyano-1,7-naphthyridin-4-yl]amino]butanamide
synonym: BAY297
synonym: compound 58 [PMID: 34699202]
approved: f
ligand name: BAY-297
type: SyntheticOrganicLigand

BAY-091
canonical SMILES: CC[C@H](C(=O)O)Nc1c(C#N)c(nc2c1ccnc2)c1ccc(cc1)c1cccc(c1F)C
in ch i key: DVIVLYHDLNAXAT-OAQYLSRUSA-N
in ch i: InChI=1S/C26H21FN4O2/c1-3-21(26(32)33)30-25-19-11-12-29-14-22(19)31-24(20(25)13-28)17-9-7-16(8-10-17)18-6-4-5-15(2)23(18)27/h4-12,14,21H,3H2,1-2H3,(H,30,31)(H,32,33)/t21-/m1/s1
comment: BAY-091 is an ATP-competitive inhibitor of the lipid modifying kinase phosphatidylinositol-5-phosphate 4-kinase type 2 alpha (PIP4K2A) <Reference id=43178/>. It was designed to aid exploration of the role(s) played by PIP4K2A and -B in pathophysiological conditions such as cancer. BAY-091 directly interacts with PIP4K2A in cells, and inhibits downstream signalling. However, this mechanism failed to translate into the expected phamacodynamic effect of antiproliferative activity in p53-deficient tumour cells, but BAY-091 remains useful as a chemical probe for in vitro analysis of PIP4K2A function.
iupac name: (2R)-2-[[3-cyano-2-[4-(2-fluoro-3-methylphenyl)phenyl]-1,7-naphthyridin-4-yl]amino]butanoic acid
synonym: BAY091
synonym: compound 60 [PMID: 34699202]
approved: f
ligand name: BAY-091
type: SyntheticOrganicLigand

firzacorvir
in ch i key: XVKTYEAUJPZPDZ-HIFRSBDPSA-N
comment: Firzacorvir is an antiviral agent. It acts as an inhibitor of hepatitis B virus (HBV) core protein (a.k.a. capsid assembly modulator or core protein allosteric modulator <Reference id=43168/>), and via this mechanism it disrupts HBV replication. This chemical structure was obtained from INN proposed list 124 (December 2020).
iupac name: (3S,5R)-N-(3-chloro-4-fluorophenyl)-2-methyl-5-[5-(1-methylimidazol-4-yl)-1,3-thiazol-2-yl]-1,1-dioxo-1,2,6-thiadiazinane-3-carboxamide
approved: f
ligand name: firzacorvir
type: SyntheticOrganicLigand

BIIB091
in ch i key: JSAQBOQCZJHWMA-XMMPIXPASA-N
in ch i: InChI=1S/C28H34N10O2/c1-28(2,3)38-15-25(34-35-38)26(39)32-24-8-10-37(21-16-40-17-21)13-19-11-18(5-6-22(19)24)23-7-9-29-27(33-23)31-20-12-30-36(4)14-20/h5-7,9,11-12,14-15,21,24H,8,10,13,16-17H2,1-4H3,(H,32,39)(H,29,31,33)/t24-/m1/s1
comment: BIIB091 was disclosed as an orthosteric, ATP-competitive inhibitor of the Tec family kinase, Bruton's tyrosine kinase (BTK) <Reference id=43167/>. It is being investigated by Biogen to block the inflammatory processes that drive neurodegeneration in multiple sclerosis. The molecule with no specified stereo centres is represented by <Ligand id=11203/>.
synonym: BIIB-091
synonym: compound 51 [PMID: 34734694]
approved: f
ligand name: BIIB091
type: SyntheticOrganicLigand

laniquidar
in ch i key: TULGGJGJQXESOO-UHFFFAOYSA-N
in ch i: InChI=1S/C37H36N4O3/c1-43-37(42)34-24-38-36-35(32-8-4-2-6-27(32)19-23-41(34)36)29-17-21-40(22-18-29)20-16-26-10-14-31(15-11-26)44-25-30-13-12-28-7-3-5-9-33(28)39-30/h2-15,24H,16-23,25H2,1H3
comment: Laniquidar (R101933) is a third generation inhibitor of the ATP-binding cassette transporter P-glycoprotein (P-gp; ABCB1) <Reference id=43159/><Reference id=43165/>. P-gp is a drug transporter and efflux pump that can promote resistance to drugs, including chemotherapeutics. Pharmacologic inhibition of P-gp is an established strategy that is being investigated to block this resistance mechanism in cancers <Reference id=43159/>.
iupac name: methyl 11-[1-[2-[4-(quinolin-2-ylmethoxy)phenyl]ethyl]piperidin-4-ylidene]-5,6-dihydroimidazo[2,1-b][3]benzazepine-3-carboxylate
xref: CHEMBL539378
approved: f
ligand name: laniquidar
type: SyntheticOrganicLigand

zosuquidar
in ch i key: IHOVFYSQUDPMCN-XAKVHENESA-N
in ch i: InChI=1S/C32H31F2N3O2/c33-32(34)29-22-7-1-3-9-24(22)31(25-10-4-2-8-23(25)30(29)32)37-17-15-36(16-18-37)19-21(38)20-39-28-13-5-12-27-26(28)11-6-14-35-27/h1-14,21,29-31,38H,15-20H2/t21-,29-,30+,31?/m1/s1
comment: Zosuquidar (LY335979) is a third generation inhibitor of the ATP-binding cassette transporter P-glycoprotein (P-gp; ABCB1) <Reference id=43162/>. P-gp is a drug transporter that can promote resistance to drugs, including chemotherapeutics. Pharmacologic inhibition of P-gp is an established strategy that is being investigated to block this resistance mechanism in cancers <Reference id=43159/>.
xref: CHEMBL444172
synonym: LY 335979
synonym: LY335979
synonym: LY-335979
approved: f
ligand name: zosuquidar
type: SyntheticOrganicLigand

tariquidar
in ch i key: LGGHDPFKSSRQNS-UHFFFAOYSA-N
in ch i: InChI=1S/C38H38N4O6/c1-45-33-18-25-14-16-42(23-28(25)19-34(33)46-2)15-13-24-9-11-29(12-10-24)40-38(44)30-20-35(47-3)36(48-4)21-32(30)41-37(43)27-17-26-7-5-6-8-31(26)39-22-27/h5-12,17-22H,13-16,23H2,1-4H3,(H,40,44)(H,41,43)
comment: Tariquidar (XR9576) is a third generation inhibitor of the ATP-binding cassette transporter P-glycoprotein (P-gp; ABCB1) <Reference id=43160/>. P-gp is a drug transporter that can promote resistance to drugs, including chemotherapeutics. Pharmacologic inhibition of P-gp is an established strategy that is being investigated to block this resistance mechanism in cancers <Reference id=43159/>.
iupac name: N-[2-[[4-[2-(6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl)ethyl]phenyl]carbamoyl]-4,5-dimethoxyphenyl]quinoline-3-carboxamide
xref: CHEMBL348475
synonym: XR9576
synonym: XR-9576
synonym: compound 2 [PMID: 10098671]
approved: f
ligand name: tariquidar
type: SyntheticOrganicLigand

WS-898
in ch i key: WGQWRCAZEPAXRA-GZTJUZNOSA-N
in ch i: InChI=1S/C33H25N7OS/c1-21-18-31(40-32(34-21)38-33(39-40)42-20-30-36-27-8-4-5-9-28(27)37-30)35-26-15-13-24(14-16-26)29(41)17-11-22-10-12-23-6-2-3-7-25(23)19-22/h2-19,35H,20H2,1H3,(H,36,37)/b17-11+
comment: WS-898 is an orally bioavailable inhibitor of the ATP-binding cassette transporter P-glycoprotein (P-gp; ABCB1) <Reference id=43158/>. P-gp is a drug transporter that can promote multidrug resistance. Pharmacologic inhibition of P-gp is an established mechanism that is being investigated to overcome resistance and/or increase sensitivity to chemotherapy drugs.
iupac name: (E)-1-(4-((2-(((1H-Benzo[d]imidazole-2-yl)methyl)thio)-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)amino)phenyl)-3-(naphthalen-2-yl)prop-2-en-1-one
synonym: WS898
synonym: compound 26 [PMID: 34723530]
approved: f
ligand name: WS-898
type: SyntheticOrganicLigand

IRAK3 PROTAC 23
in ch i key: ZUODKONSNNHSAJ-AMLBMYBGSA-N
in ch i: InChI=1S/C47H63N11O6/c1-31(2)36-16-20-57-43(36)44(48-30-49-57)50-33-3-5-34(6-4-33)53-25-27-56(28-26-53)42(61)12-11-41(60)55-18-14-32(15-19-55)13-17-52-21-23-54(24-22-52)35-7-8-37-38(29-35)47(64)58(46(37)63)39-9-10-40(59)51-45(39)62/h7-8,16,20,29-34,39H,3-6,9-15,17-19,21-28H2,1-2H3,(H,48,49,50)(H,51,59,62)/t33-,34+,39?
comment: This molecule is aproteolysis-targeting chimera (PROTAC) degrader of interleukin 1 receptor associated kinase 3 (IRAK3) <Reference id=43157/>. It promotes ternary complex formation between IRAK3 and the cereblon (CRBN) E3 ubiquitin ligase. IRAK3 is a regulatory protein that suppresses proinflammatory signalling in monocytes, macrophages, and neutrophils. Blocking IRAK3's immunosuppressive function is being investigated as an anti-tumour mechanism <Reference id=30836/>.
synonym: compound 23 [PMID: 32803978]
approved: f
ligand name: IRAK3 PROTAC 23
type: SyntheticOrganicLigand

AZ14117230
in ch i key: CQSOTYMFUWTIIR-HUSBZTEESA-N
comment: AZ14117230 is a proteolysis-targeting chimera (PROTAC) molecule that targets the embryonic ectoderm development (EED) protein for degradation by promoting ternary complex formation with the VHL E3 ubiquitin ligase <Reference id=43156/>. A second EED PROTAC (AZ14118579, compound 3) is also reported in the Hsu et al. article <Reference id=43156/>. EED is a subunit of the PRC2 complex (alongside EZH2 and SUZ12) that promotes tumourigenesis by driving aberrant hypermethylation of H3K27.
iupac name: (2S,4R)-1-[(2S)-2-[5-[3-[5-[5-[(5-fluoro-2,3-dihydro-1-benzofuran-4-yl)methylamino]-[1,2,4]triazolo[4,3-c]pyrimidin-8-yl]-6-methylpyridin-2-yl]propanoylamino]pentanoylamino]-3,3-dimethylbutanoyl]-4-hydroxy-N-[[4-(4-methyl-1,3-thiazol-5-yl)phenyl]methyl]pyrrolidine-2-carboxamide
synonym: EED PROTAC 1
synonym: AZ-14117230
synonym: compound 2 [PMID: 31786184]
approved: f
ligand name: AZ14117230
type: SyntheticOrganicLigand

AZD5991
in ch i key: KBQCEQAXHPIRTF-UHFFFAOYSA-N
comment: AZD5991 is an oncology clinical lead. Structurally it is a BH3 mimetic that inhibits function of the MCL1 apoptosis regulator protein (Mcl-1) and induces apoptosis <Reference id=43155/><Reference id=43154/>. AZD5991 was designed by AstraZeneca for potential to treat haematologic malignancies such as chronic lymphocytic leukemia and multiple myeloma.
xref: CHEMBL4297482
synonym: AZD-5991
approved: f
ligand name: AZD5991
type: SyntheticOrganicLigand

AZD4573
in ch i key: AVIWDYSJSPOOAR-LSDHHAIUSA-N
in ch i: InChI=1S/C22H28ClN5O2/c1-13(29)26-15-6-4-5-14(7-15)21(30)27-20-8-16(18(23)11-24-20)17-10-25-28-12-22(2,3)9-19(17)28/h8,10-11,14-15H,4-7,9,12H2,1-3H3,(H,26,29)(H,24,27,30)/t14-,15+/m0/s1
comment: AZD4573 is a potent inhibitor of cyclin dependent kinase 9 (CDK9), that was designed for potential to treat haematological malignancies <Reference id=43151/><Reference id=43152/><Reference id=43153/>. Inhibition of CDK9 disrupts the expression of cancer-promoting genes such as MCL-1, and induces apoptosis.
iupac name: (1S,3R)-3-acetamido-N-[5-chloro-4-(5,5-dimethyl-4,6-dihydropyrrolo[1,2-b]pyrazol-3-yl)pyridin-2-yl]cyclohexane-1-carboxamide
xref: CHEMBL4462530
synonym: AZD-4573
synonym: compound 24 [PMID: 33306391]
approved: f
ligand name: AZD4573
type: SyntheticOrganicLigand

AZD4320
in ch i key: UNEJSHNDABUZNY-UJNHCCGESA-N
comment: AZD4320 is a BH3 mimetic, dual inhibitor of Bcl2 and Bcl-xL <Reference id=43149/>. It induces apoptosis in haematological cancer cell lines and in some solid tumour cell types. A PEGylated/poly-lysine congugated version of AZD4320 (AZD0466) was designed to improve AZD4320's dose limiting cardiovascular toxicity (identified in preclinical species), and to optimise its physicochemical properties.
xref: CHEMBL3703600
synonym: AZD-4320
synonym: Example 3 [US9248140B2]
approved: f
ligand name: AZD4320
type: SyntheticOrganicLigand

BMS-911172
in ch i key: GCTFTMWXZFLTRR-GFCCVEGCSA-N
in ch i: InChI=1S/C16H19F2N3O3/c1-9(2)5-12(19)15(22)21-10-3-4-11(14-7-20-8-23-14)13(6-10)24-16(17)18/h3-4,6-9,12,16H,5,19H2,1-2H3,(H,21,22)/t12-/m1/s1
comment: BMS-911172 is a small molecule, brain-penetrant inhibitor of AP2 associated kinase 1 (AAK1) <Reference id=42690/>. It was designed by Bristol Myers Squibb as a tool to validate AAK1 as a molecular target for the treatment of neuropathic pain. BMS-911172 was effictive in rat models of persistent and neuropathic pain.
iupac name: (2R)-2-amino-N-[3-(difluoromethoxy)-4-(1,3-oxazol-5-yl)phenyl]-4-methylpentanamide
synonym: BMS911172
synonym: compound 59 [PMID: 34270254]
approved: f
ligand name: BMS-911172
type: SyntheticOrganicLigand

AZ6102
in ch i key: WCPTUQOMNJBIET-CALCHBBNSA-N
in ch i: InChI=1S/C25H28N6O/c1-15-11-22(31-13-16(2)27-17(3)14-31)26-12-21(15)18-5-7-19(8-6-18)23-28-24-20(25(32)29-23)9-10-30(24)4/h5-12,16-17,27H,13-14H2,1-4H3,(H,28,29,32)/t16-,17+
comment: AZ6102 is a small molecule inhibitor of the tankyrases TNKS1 and TNKS2 <Reference id=38812/>. Blocking tankyrase activity inhibits the Wnt signalling pathway via increased stabilisation of axin. AZ6102 was developed for potential anti-proliferative activity against certain cancers cells.
xref: CHEMBL4101890
synonym: AZ-6102
synonym: compound 25 [PMID: 25815142]
approved: f
ligand name: AZ6102
type: SyntheticOrganicLigand

BCL6 PROTAC 15
in ch i key: YQWUMLVLLIWGQJ-UYEDPJPISA-N
comment: This is a bivalent proteolysis-targeting chimera (PROTAC) molecule that promotes the degradation of the BCL6 transcription repressor protein <Reference id=43147/>. It comprises a BCL6 binding domain linked to a thalidomide warhead that targets the bound BCL6 to the E3 ubiquitin ligase cereblon (CRBN), and on to ubiquitin-mediated proteosomal degradation. PROTAC 15 was developed by AstraZeneca for potential to treat lymphomas that are derived from germinal center B cells. Although PROTAC 15 leads to BCL6 degradation in vitro, the degradation is incomplete, and this produces only a weak antiproliferative effect on target diffuse large B-cell lymphoma (DLBCL) cells.
synonym: compound 15 [PMID: 30335946]
approved: f
ligand name: BCL6 PROTAC 15
type: SyntheticOrganicLigand

SIM1
in ch i key: RARNTROXRCXFHV-CMRSQZKGSA-N
comment: SIM1 is a first-in-class trivalent PROTAC molecule <Reference id=43146/>. It contains two bromo and extra terminal (BET) domain inhibitor ligand components and a von Hippel-Lindau (VHL) ligand domain which are tethered together by a branched linker. This approach increases the valency for target protein binding compared to earlier generation bivalent PROTAC molecules. SIM1 acts as a low picomolar BET degrader in vitro, and has favourable in vivo pharmacokinetics. BET inhibitors are being explored for anticancer activity.
iupac name: N,N'-(11-((2-(((S)-1-((2S,4R)-4-hydroxy-2-((4-(4-methylthiazol-5-yl)benzyl)carbamoyl)pyrrolidin-1-yl)- 3,3-dimethyl-1-oxobutan-2-yl)amino)-2-oxoethoxy)methyl)-11-methyl-3,6,9,13,16,19- hexaoxahenicosane-1,21-diyl)bis(2-((S)-4-(4-chlorophenyl)-2,3,9-trimethyl-6H-thieno[3,2- f][1,2,4]triazolo[4,3-a][1,4]diazepin-6-yl)acetamide)
synonym: compound 3 [PMID: 34675414]
approved: f
ligand name: SIM1
type: SyntheticOrganicLigand

compound 6 [PMID: 34553947]
in ch i key: LQVIUEMPEFSVOL-CPRIZNHFSA-N
comment: Compound 6 is a selective beta-secretase 1 (BACE1) inhibitor <Reference id=43133/>. Orally administered compound 6 reduced Aβ by ~50% in mouse brain 2 h after dosing.
iupac name: N-(3-((4R,5R,6R)-2-Amino-5-fluoro-4,6-dimethyl-5,6-dihydro-4H-1,3-thiazin-4-yl)-4-fluorophenyl)-2,3-dihydro-[1,4]dioxino[2,3-c]pyridine-7-carboxamide
approved: f
ligand name: compound 6 [PMID: 34553947]
type: SyntheticOrganicLigand

compound 7d [PMID: 34528437]
canonical SMILES: C=CCn1ccc2c1cccc2C(=O)Oc1cncc(c1)Cl
isomeric SMILES: C=CCn1ccc2c1cccc2C(=O)Oc1cc(Cl)cnc1
in ch i key: XBVPAGLILYEOGS-UHFFFAOYSA-N
in ch i: InChI=1S/C17H13ClN2O2/c1-2-7-20-8-6-14-15(4-3-5-16(14)20)17(21)22-13-9-12(18)10-19-11-13/h2-6,8-11H,1,7H2
comment: Compound 7d is reported as a potent SARS-CoV-2 chymotrypsin-like protease (3CLpro; Mpro) inhibitor <Reference id=43107/>.
iupac name: 5-Chloropyridin-3-yl 1-allyl-1H-indole-4-carboxylate
approved: f
ligand name: compound 7d [PMID: 34528437]
type: SyntheticOrganicLigand

XR8-24
in ch i key: ZTKSBNLNPMUGBL-HXUWFJFHSA-N
in ch i: InChI=1S/C28H34N4OS/c1-19-8-9-23(31-24-16-29-17-24)15-26(19)28(33)30-20(2)21-6-5-7-22(14-21)27-11-10-25(34-27)18-32-12-3-4-13-32/h5-11,14-15,20,24,29,31H,3-4,12-13,16-18H2,1-2H3,(H,30,33)/t20-/m1/s1
comment: XR8-24 is reported as a lead SARS-CoV-2 papain-like protease (PLpro) inhibitor <Reference id=43105/><Reference id=43106/>.
iupac name: 5-[(azetidin-3-yl)amino]-2-methyl-N-[(1R)-1-(3-{5-[(pyrrolidin-1-yl)methyl]thiophen-2-yl}phenyl)ethyl]benzamide
synonym: compound 74 [PMID: 34665619]
approved: f
ligand name: XR8-24
type: SyntheticOrganicLigand

XR8-23
in ch i key: PKMUHQIDVVOXHQ-HXUWFJFHSA-N
in ch i: InChI=1S/C29H36N4OS/c1-19-10-11-24(33-25-16-30-17-25)15-27(19)29(34)32-20(2)21-6-5-7-22(14-21)28-13-12-26(35-28)18-31-23-8-3-4-9-23/h5-7,10-15,20,23,25,30-31,33H,3-4,8-9,16-18H2,1-2H3,(H,32,34)/t20-/m1/s1
comment: XR8-23 is reported as a lead SARS-CoV-2 papain-like protease (PLpro) inhibitor <Reference id=43105/>.
synonym: compound 72 [PMID: 34665619]
approved: f
ligand name: XR8-23
type: SyntheticOrganicLigand

MAT-POS-932d1078-3
in ch i key: RMXNRMBUTBCRQX-FQEVSTJZSA-N
in ch i: InChI=1S/C20H16F2N2O3/c1-26-20(6-7-27-18-15(20)8-13(21)9-16(18)22)19(25)24-17-11-23-10-12-4-2-3-5-14(12)17/h2-5,8-11H,6-7H2,1H3,(H,24,25)/t20-/m0/s1
comment: MAT-POS-932d1078-3 is a novel, non-covalent SARS-CoV-2 Mpro (3CLpro) inhibitor that emerged from the COVID Moonshot Consortium's drug discovery campaign <Reference id=43104/>. It has good drug-like properties, including favourable metabolic stability and predicted oral bioavailability.
approved: f
ligand name: MAT-POS-932d1078-3
type: SyntheticOrganicLigand

BMS-986158
in ch i key: KGERZPVQIRYWRK-GDLZYMKVSA-N
in ch i: InChI=1S/C30H33N5O2/c1-19-28(34(4)33-32-19)22-16-26-27(31-18-22)24-11-10-23(30(2,3)36)17-25(24)35(26)29(20-8-6-5-7-9-20)21-12-14-37-15-13-21/h5-11,16-18,21,29,36H,12-15H2,1-4H3/t29-/m1/s1
comment: BMS-986158 is a clinical candidate inhibitor of bromodomain and extra-terminal (BET) domain-containing proteins <Reference id=43071/>. It was developed as a potential treatment for haematologic and solid tumours. Early pan-BET inhibitors include <Ligand id=7511/> and <Ligand id=7033/> (GSK525762), but some tumours are either inherently resistant to these inhibitors <Reference id=43072/>, or develop treatment-induced resistance <Reference id=43073/>. BMS-986158 was designed on a different chemical scaffold to combat resistance issues.
iupac name: 2-[3-(3,5-dimethyltriazol-4-yl)-5-[(S)-oxan-4-yl(phenyl)methyl]pyrido[3,2-b]indol-7-yl]propan-2-ol
xref: CHEMBL4297458
synonym: BMS986158
synonym: compound 18 [PMID: 34543572]
approved: f
ligand name: BMS-986158
type: SyntheticOrganicLigand

sivopixant
in ch i key: SKZQFKBIJUXXCG-INIZCTEOSA-N
in ch i: InChI=1S/C25H22ClN5O5/c1-16(22(32)33)14-31-24(34)29-23(30(25(31)35)15-17-5-7-18(26)8-6-17)28-19-9-11-20(12-10-19)36-21-4-2-3-13-27-21/h2-13,16H,14-15H2,1H3,(H,32,33)(H,28,29,34)/t16-/m0/s1
comment: Sivopixant (S-600918) is a clinical stage, oral P2X3 ion channel antagonist <Reference id=43069/>.
iupac name: (2S)-3-[3-[(4-chlorophenyl)methyl]-2,6-dioxo-4-(4-pyridin-2-yloxyanilino)-1,3,5-triazin-1-yl]-2-methylpropanoic acid
synonym: S-600918
synonym: compound 28 [PMID: 34587541]
approved: f
ligand name: sivopixant
type: SyntheticOrganicLigand

ARD-2585
in ch i key: LUCHABJUYSYJAT-RVWRWSNSSA-N
in ch i: InChI=1S/C41H43ClN8O5/c1-46(30-9-4-26(22-43)35(42)21-30)28-10-5-27(6-11-28)44-38(52)25-2-7-29(8-3-25)47-16-18-48(19-17-47)32-23-49(24-32)31-12-13-33-34(20-31)41(55)50(40(33)54)36-14-15-37(51)45-39(36)53/h2-4,7-9,12-13,20-21,27-28,32,36H,5-6,10-11,14-19,23-24H2,1H3,(H,44,52)(H,45,51,53)/t27-,28-,36?
comment: ARD-2585 is a highly potent and orally bioavailable PROTAC androgen receptor (AR) degrader molecule <Reference id=43068/>. It was designed to reduce AR in metastatic castration-resistant prostate cancer (mCRPC), as an alternative mechanism to antagonising AR signaling with drugs such as <Ligand id=6812/> and <Ligand id=9043/>. Structurally ARD-2585 is a bifunctional molecule that contains an AR antagonist ligand linked to a cereblon binding component, that targets the AR to the cereblon/cullin 4A E3 ligase complex for degradation. It shares structural similarities to <Ligand id=11512/>, which was the first AR PROTAC to advance to clinical evaluation in humans.
synonym: ARD2585
synonym: compound 43 [PMID: 34473519]
approved: f
ligand name: ARD-2585
type: SyntheticOrganicLigand

milvexian
in ch i key: FSWFYCYPTDLKON-CMJOXMDJSA-N
comment: Milvexian (BMS-986177) is a clinical stage, macrocyclic, oral anti-coagulant. Mechanistically it is a factor XIa inhibitor <Reference id=43063/><Reference id=43062/>. Inhibiting factor XIa reduces thrombus formation without significantly altering hemostasis.
xref: CHEMBL4112929
synonym: BMS-986177
synonym: BMS986177
synonym: JNJ-70033093
synonym: JNJ70033093
synonym: compound 17 [PMID: 34494428]
approved: f
ligand name: milvexian
type: SyntheticOrganicLigand

ETX0462
in ch i key: TVYRNFNEBLNAMJ-XPUUQOCRSA-N
in ch i: InChI=1S/C10H16N6O7S/c1-11-9(13-19)8-7-5(3-12-15(7)2)6(4-16(8)10(17)18)14-23-24(20,21)22/h3,6,8,14,19H,4H2,1-2H3,(H,11,13)(H,17,18)(H,20,21,22)/t6-,8-/m0/s1
comment: ETX0462 is a diazabicyclooctane molecule that represents a new class of antibacterial. It is a β-lactamase inhibitor that also acts as a single agent antibacterial through its capacity to inhibit penicillin-binding proteins <Reference id=43061/>. It has a broad-spectrum of activity (in vitro and in vivo) against Gram-negative bacteria including virulent and antibacterial resistant ESKAPE pathogens (Enterococcus faecium, Staphylococcus aureus, Klebsiella pneumoniae, Acinetobacter baumannii, Pseudomonas aeruginosa, and Enterobacter species), Stenotrophomonas maltophilia and bacterial agents that might be used as biological weapons. Further optimisation of ETX0462 is required to improve its permeability across bacterial outer membranes and increase its biochemical potency. The crystal structure of ETX0462 bound to P. aeruginosa penicillin binding protein 3 (PBP3) has been resolved at a resolution of 2.2 Å (PDB ID: 7JWL) <Reference id=43061/>.
synonym: ETX-0462
synonym: VMM
approved: f
ligand name: ETX0462
type: SyntheticOrganicLigand

FRM-024
in ch i key: IOQORVDNYPOZPL-VQTJNVASSA-N
in ch i: InChI=1S/C22H22ClN5O2/c1-13-11-28(12-24-13)18-10-9-17(25-22(18)29-2)21-26-19(14-5-7-16(23)8-6-14)20(30-27-21)15-3-4-15/h5-12,15,19-20H,3-4H2,1-2H3,(H,26,27)/t19-,20+/m0/s1
comment: FRM-024 is a CNS-penetrating γ secretase modulator that was developed for its capacity to improve amyloid processing and potential as an Alzheimer's disease therapeutic <Reference id=43056/>. Gamma secretase modulators reduce the levels of the toxic longer amyloid β (Aβ) chains (Aβ42, Aβ43) that accummulate in Alzheimer's brains. They do not alter total Aβ levels. In particular, such modulators may afford potential for clinical intervention in patients with inherited loss-of-function mutations in presenilin genes which increase production of the toxic forms of Aβ.
iupac name: (5S,6R)-5-(4-chlorophenyl)-6-cyclopropyl-3-[6-methoxy-5-(4-methylimidazol-1-yl)pyridin-2-yl]-5,6-dihydro-2H-1,2,4-oxadiazine
synonym: FRM024
synonym: compound 41 [PMID: 34550687]
approved: f
ligand name: FRM-024
type: SyntheticOrganicLigand

JNJ-67569762
in ch i key: NDIQAOIHFVWZJQ-NHCUHLMSSA-N
comment: JNJ-67569762 is a selective beta-secretase 1 (BACE1) inhibitor <Reference id=43055/>. The compound delivered the predicted pharmacodynamic effect (reducing amyloid β) in vivo, but was also found to produce a prolonged QTc signal in dogs, despite exhibiting minimal in vitro activity vs. hERG. The unexpected effect on QTc precluded JNJ-67569762 from clinical development.
iupac name: N-[3-[(2S,5R)-6-amino-5-ethylsulfonyl-2-(fluoromethyl)-5-methyl-3,4-dihydropyridin-2-yl]-4-fluorophenyl]-2,2-difluoro-[1,3]dioxolo[4,5-c]pyridine-6-carboxamide
synonym: JNJ67569762
synonym: compound 12 [PMID: 34553934]
approved: f
ligand name: JNJ-67569762
type: SyntheticOrganicLigand

GSK3685032
canonical SMILES: CCc1c(C#N)c(nc(c1C#N)N1CCC(CC1)N)SC(c1ccccc1)C(=O)N
isomeric SMILES: CCc1c(C#N)c(nc(SC(C(=O)N)c2ccccc2)c1C#N)N1CCC(N)CC1
in ch i key: KNKHRZYILDZLRE-UHFFFAOYSA-N
in ch i: InChI=1S/C22H24N6OS/c1-2-16-17(12-23)21(28-10-8-15(25)9-11-28)27-22(18(16)13-24)30-19(20(26)29)14-6-4-3-5-7-14/h3-7,15,19H,2,8-11,25H2,1H3,(H2,26,29)
comment: GSK3685032 is a first-in-class, non-nucleoside, reversible inhibitor of the epigenetic target DNA-methyltransferase 1 (DNMT1), that was identified from >1.8 million small molecules using a high-throughput enzymatic activity assay <Reference id=43054/>. It was developed for potential to treat haematological cancers. GSK3685032 is selective for DNMT1 and does not affect the activities of DNMT3A or DNMT3B. This means that it is less toxic to normal blood cells than less selective hypomethylating agents such as <Ligand id=6805/>. GSK3685032 is active in vitro and in vivo, promoting loss of DNA methylation, and inhibiting transcriptional activation and cancer cell growth.
synonym: GSK-3685032
approved: f
ligand name: GSK3685032
type: SyntheticOrganicLigand

onametostat
in ch i key: DBSMLQTUDJVICQ-CJODITQLSA-N
in ch i: InChI=1S/C22H23BrN6O2/c23-15-8-12-3-1-11(7-16(12)28-21(15)25)2-4-13-9-17(19(31)18(13)30)29-6-5-14-20(24)26-10-27-22(14)29/h1,3,5-8,10,13,17-19,30-31H,2,4,9H2,(H2,25,28)(H2,24,26,27)/t13-,17+,18+,19-/m0/s1
comment: Onametostat (JNJ-64619178) is a small molecule inhibitor of protein arginine methyltransferase 5 (PRMT5) <Reference id=43053/>. It was developed for anti-tumour potential. Onametostat occupies the S-adenosylmethionine and substrate pockets of PRMT5 and traps the enzyme (in complex with its cofactor MEP50; WDR77) in a catalytically inactive conformation. The compound has a very slow off-rate.
iupac name: (1S,2R,3S,5R)-3-[2-(2-amino-3-bromoquinolin-7-yl)ethyl]-5-(4-aminopyrrolo[2,3-d]pyrimidin-7-yl)cyclopentane-1,2-diol
xref: CHEMBL4249337
synonym: JNJ-64619178
synonym: Example 80 [WO2017032840A1]
synonym: JNJ45031882
approved: f
ligand name: onametostat
type: SyntheticOrganicLigand

baloxavir marboxil
in ch i key: RZVPBGBYGMDSBG-GGAORHGYSA-N
comment: Baloxavir marboxil is an orally delivered anti-influenza virus drug. It is a prodrug that is converted to baloxavir <Reference id=43048/>. Mechanistically baloxavir is a first-in-class inhibitor of the cap-endonuclease (CEN) activity of an acidic protein within the viral polymerase complex <Reference id=43049/> that is essential for viral gene transcription and replication. Alternative influenza antivirals (e.g. <Ligand id=11427/>, peramivir and zanamivir) target the neuraminidase enzyme that is required for fusion and entry of virus into the host cells, and the budding process that releases newly synthesised virions.
xref: CHEMBL4297503
synonym: Xofluza®
synonym: S033188
synonym: S-033188
approved: t
ligand name: baloxavir marboxil
type: SyntheticOrganicLigand

BPR1R024
in ch i key: ORYMWWSJZRCUSV-UHFFFAOYSA-N
in ch i: InChI=1S/C24H21F3N6O2/c1-33(2)17-6-9-19-20(11-17)30-14-31-22(19)35-18-7-4-16(5-8-18)32-23(34)29-13-15-3-10-21(28-12-15)24(25,26)27/h3-12,14H,13H2,1-2H3,(H2,29,32,34)
comment: BPR1R024 is an orally active inhibitor of colony stimulating factor 1 receptor (CSF1R) tyrosine kinase activity <Reference id=43027/>. It was developed for immunomodulatory antitumour potential.
iupac name: 1-[4-[7-(dimethylamino)quinazolin-4-yl]oxyphenyl]-3-[[6-(trifluoromethyl)pyridin-3-yl]methyl]urea
synonym: BPR1R-024
synonym: compound 12 [PMID: 34606263]
approved: f
ligand name: BPR1R024
type: SyntheticOrganicLigand

AS-0141
canonical SMILES: CCOC(=O)C1=C(NN2CCN(CC2)CC(F)(F)F)O/C(=C/c2c[nH]c3c2cccn3)/C1=O
isomeric SMILES: FC(F)(F)CN1CCN(NC2=C(C(=O)OCC)C(=O)/C(=C/c3c[nH]c4c3cccn4)/O2)CC1
in ch i key: DNTVXDZWVOVLOD-GDNBJRDFSA-N
in ch i: InChI=1S/C21H22F3N5O4/c1-2-32-20(31)16-17(30)15(10-13-11-26-18-14(13)4-3-5-25-18)33-19(16)27-29-8-6-28(7-9-29)12-21(22,23)24/h3-5,10-11,27H,2,6-9,12H2,1H3,(H,25,26)/b15-10-
comment: AS-0141 is an oral and selective CDC7 kinase inhibitor, that was developed for potential to treat cancer <Reference id=43026/>.
iupac name: ethyl 4-hydroxy-5-(pyrrolo[2,3-b]pyridin-3-ylidenemethyl)-2-[[4-(2,2,2-trifluoroethyl)piperazin-1-yl]amino]furan-3-carboxylate
synonym: AS0141
synonym: compound 24 [PMID: 34607435]
approved: f
ligand name: AS-0141
type: SyntheticOrganicLigand

valspodar
in ch i key: YJDYDFNKCBANTM-QCWCSKBGSA-N
comment: Valspodar is a cyclosporin analogue. It inhibits the multidrug resistance efflux pump/transporter, p-glycoprotein (ABCB1) and via this mechanism can reverse cancer cell resistance to chemotherapeutics in cancers that overexpress ABCB1 <Reference id=43021/>. Valspodar does not induce the immunosuppressive effects of cyclosporin A.
xref: CHEMBL1086218
synonym: 3'-keto-Bmt(1)-Val(2)-cyclosporin A
synonym: PSC-833
synonym: PSC833
synonym: SDZ-PSC-833
synonym: SDZ PSC 833
synonym: Amdray®
synonym: SDZ PSC833
approved: f
ligand name: valspodar
type: PeptideLigand

aranidipine
canonical SMILES: COC(=O)C1=C(C)NC(=C(C1c1ccccc1[N+](=O)[O-])C(=O)OCC(=O)C)C
in ch i key: NCUCGYYHUFIYNU-UHFFFAOYSA-N
in ch i: InChI=1S/C19H20N2O7/c1-10(22)9-28-19(24)16-12(3)20-11(2)15(18(23)27-4)17(16)13-7-5-6-8-14(13)21(25)26/h5-8,17,20H,9H2,1-4H3
comment: Aranidipine (MPC-1304) is a long-acting, dihydropyridine-type Ca2+ channel blocker <Reference id=43017/> that produces an hypotensive effect in vivo <Reference id=43018/>. Activation of K+ channels may also be involved in aranidipine-induced vasodilation, as identified in a rat model <Reference id=43016/>. We show the compound with no specified stereochemistry to represent the racemic mixture of enantiomers. It has been reported that the (S) enantiomer of aranidipine is responsible for most of the pharmacological activity of the racemate <Reference id=43019/>.
iupac name: 3-O-methyl 5-O-(2-oxopropyl) 2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate
xref: CHEMBL2104030
synonym: MPC-1304
synonym: MPC1304
synonym: Sapresta®
approved: t
ligand name: aranidipine
type: SyntheticOrganicLigand

SU5402
canonical SMILES: OC(=O)CCc1c([nH]cc1C)/C=C/1/C(=O)Nc2c1cccc2
isomeric SMILES: Cc1c[nH]c(c1CCC(=O)O)/C=C/1/c2ccccc2NC1=O
in ch i key: JNDVEAXZWJIOKB-JYRVWZFOSA-N
in ch i: InChI=1S/C17H16N2O3/c1-10-9-18-15(11(10)6-7-16(20)21)8-13-12-4-2-3-5-14(12)19-17(13)22/h2-5,8-9,18H,6-7H2,1H3,(H,19,22)(H,20,21)/b13-8-
comment: SU5402 is an inhibitor of the enzymatic activity of receptor tyrosine kinases, including kinase insert domain receptor (VEGFR-2), fibroblast growth factor receptor 1 (FGFR1) and platelet derived growth factor receptor beta (PDGFRβ) <Reference id=25970/>.
iupac name: 3-[4-methyl-2-[(Z)-(2-oxo-1H-indol-3-ylidene)methyl]-1H-pyrrol-3-yl]propanoic acid
xref: CHEMBL89363
synonym: compound 1 [PMID: 10602697]
synonym: SU-5402
approved: f
ligand name: SU5402
type: SyntheticOrganicLigand

bifemelane
canonical SMILES: CNCCCCOc1ccccc1Cc1ccccc1
isomeric SMILES: CNCCCCOc1ccccc1Cc1ccccc1
in ch i key: QSQQPMHPCBLLGX-UHFFFAOYSA-N
in ch i: InChI=1S/C18H23NO/c1-19-13-7-8-14-20-18-12-6-5-11-17(18)15-16-9-3-2-4-10-16/h2-6,9-12,19H,7-8,13-15H2,1H3
comment: Bifemelane acts as a monoamine oxidase inhibitor <Reference id=43015/>, with inhibitory activity against both MAO-A (competitive) and MAO-B (noncompetitive). It has nootropic, neuroprotective, and antidepressant effects in vivo.
iupac name: 4-(2-benzylphenoxy)-N-methylbutan-1-amine
xref: CHEMBL1192517
synonym: Alnert®
synonym: Celeport®
synonym: BP-N-methylbutylamine
synonym: MCI-2016
synonym: MCI2016
approved: t
ligand name: bifemelane
type: SyntheticOrganicLigand

biricodar
in ch i key: CGVWPQOFHSAKRR-NDEPHWFRSA-N
in ch i: InChI=1S/C34H41N3O7/c1-41-29-20-26(21-30(42-2)32(29)43-3)31(38)33(39)37-19-5-4-16-28(37)34(40)44-27(14-6-10-24-12-8-17-35-22-24)15-7-11-25-13-9-18-36-23-25/h8-9,12-13,17-18,20-23,27-28H,4-7,10-11,14-16,19H2,1-3H3/t28-/m0/s1
comment: Biricodar (VX-710) acts as an inhibitor of the ABCB1 and ABCC1 transporters (a.k.a. P-glycoprotein and multidrug resistance protein 1 respectively) <Reference id=43014/>. It restores sensitivity to chemotherapeutic agents in cancer cells that use these efflux pumps to induce drug resistance. Biricodar was developed as an adjunct to chemotherapeutic drugs, for potential in cancer therapy, but it was never apporved for clinical use.
iupac name: 1,7-dipyridin-3-ylheptan-4-yl (2S)-1-[2-oxo-2-(3,4,5-trimethoxyphenyl)acetyl]piperidine-2-carboxylate
xref: CHEMBL350775
synonym: VX-710
synonym: VX710
synonym: Incel®
approved: f
ligand name: biricodar
type: SyntheticOrganicLigand

lacidipine
canonical SMILES: CCOC(=O)C1=C(C)NC(=C(C1c1ccccc1/C=C/C(=O)OC(C)(C)C)C(=O)OCC)C
isomeric SMILES: CCOC(=O)C1=C(NC(=C(C1c1ccccc1/C=C/C(=O)OC(C)(C)C)C(=O)OCC)C)C
in ch i key: GKQPCPXONLDCMU-CCEZHUSRSA-N
in ch i: InChI=1S/C26H33NO6/c1-8-31-24(29)21-16(3)27-17(4)22(25(30)32-9-2)23(21)19-13-11-10-12-18(19)14-15-20(28)33-26(5,6)7/h10-15,23,27H,8-9H2,1-7H3/b15-14+
comment: Lacidipine (GR-43659X) is dihydropyridine calcium channel blocker. It has a slow onset of activity and a long duration of action.
iupac name: diethyl 2,6-dimethyl-4-[2-[(E)-3-[(2-methylpropan-2-yl)oxy]-3-oxoprop-1-enyl]phenyl]-1,4-dihydropyridine-3,5-dicarboxylate
synonym: GR-43659X
synonym: GR43659X
synonym: Motens®
synonym: Lacipil®
synonym: GX1048
synonym: GX 1048
synonym: GX-1048
synonym: Molap®
approved: t
ligand name: lacidipine
type: SyntheticOrganicLigand

manidipine
in ch i key: ANEBWFXPVPTEET-UHFFFAOYSA-N
in ch i: InChI=1S/C35H38N4O6/c1-24-30(34(40)44-3)32(28-15-10-16-29(23-28)39(42)43)31(25(2)36-24)35(41)45-22-21-37-17-19-38(20-18-37)33(26-11-6-4-7-12-26)27-13-8-5-9-14-27/h4-16,23,32-33,36H,17-22H2,1-3H3
comment: Manidipine (CV-4093) is dihydropyridine calcium channel blocker.
iupac name: 5-O-[2-(4-benzhydrylpiperazin-1-yl)ethyl] 3-O-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate
xref: CHEMBL312176
synonym: CV-4093
synonym: CV4093
synonym: Artedil®
synonym: Franidipine®
synonym: Iperten®
approved: t
ligand name: manidipine
type: SyntheticOrganicLigand

mirodenafil
in ch i key: MIJFNYMSCFYZNY-UHFFFAOYSA-N
in ch i: InChI=1S/C26H37N5O5S/c1-4-7-19-18-30(6-3)24-23(19)27-25(28-26(24)33)21-17-20(8-9-22(21)36-16-5-2)37(34,35)31-12-10-29(11-13-31)14-15-32/h8-9,17-18,32H,4-7,10-16H2,1-3H3,(H,27,28,33)
comment: Mirodenafil (SK-3530) is a selective, oral phosphodiesterase type 5 (PDE5). PDE5 inhibitors are the most widely used drugs to treat erectile dysfunction <Reference id=43009/>.
iupac name: 5-ethyl-2-[5-[4-(2-hydroxyethyl)piperazin-1-yl]sulfonyl-2-propoxyphenyl]-7-propyl-3H-pyrrolo[3,2-d]pyrimidin-4-one
xref: CHEMBL4297518
synonym: SK-3530
synonym: SK3530
synonym: Mvix®
approved: t
ligand name: mirodenafil
type: SyntheticOrganicLigand

temocaprilat
in ch i key: KZVWEOXAPZXAFB-BQFCYCMXSA-N
in ch i: InChI=1S/C21H24N2O5S2/c24-19(25)12-23-11-18(17-7-4-10-29-17)30-13-16(20(23)26)22-15(21(27)28)9-8-14-5-2-1-3-6-14/h1-7,10,15-16,18,22H,8-9,11-13H2,(H,24,25)(H,27,28)/t15-,16-,18-/m0/s1
comment: Temocaprilat is the active metabolite of temocapril (the approved drug) <Reference id=43008/>. It is a competitive inhibitor of angiotensin-converting enzyme (ACE), and it has antihypertensive activity.
iupac name: (2S)-2-[[(2S,6R)-4-(carboxymethyl)-5-oxo-2-thiophen-2-yl-1,4-thiazepan-6-yl]amino]-4-phenylbutanoic acid
xref: CHEMBL300841
synonym: RS5139
synonym: RS-5139
synonym: RNH 5139
synonym: RNH-5139
synonym: RNH5139
synonym: compound 24c [PMID: 3669006]
approved: f
ligand name: temocaprilat
type: SyntheticOrganicLigand

temocapril
in ch i key: FIQOFIRCTOWDOW-BJLQDIEVSA-N
in ch i: InChI=1S/C23H28N2O5S2/c1-2-30-23(29)17(11-10-16-7-4-3-5-8-16)24-18-15-32-20(19-9-6-12-31-19)13-25(22(18)28)14-21(26)27/h3-9,12,17-18,20,24H,2,10-11,13-15H2,1H3,(H,26,27)/t17-,18-,20-/m0/s1
comment: Temocapril (CS-622) is an angiotensin converting enzyme (ACE) inhibitor prodrug <Reference id=43007/>.
iupac name: 2-[(2S,6R)-6-[[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino]-5-oxo-2-thiophen-2-yl-1,4-thiazepan-4-yl]acetic acid
xref: CHEMBL2110627
synonym: CS-622
synonym: CS622
approved: t
ligand name: temocapril
type: SyntheticOrganicLigand

compound 18n [PMID: 34382802]
canonical SMILES: CCOc1ccc(c2c1cccn2)S(=O)(=O)Nc1ccc(cc1C#Cc1cnc(cc1OC)C(=O)O)Cl
in ch i key: FNBUZGRPJLEIMO-UHFFFAOYSA-N
comment: Compound 18n is a chemical tool that is suitable for exploring the function of monocarboxylate transporter 4 (MCT4: SLC16A3) <Reference id=42990/>. MCT4 and its role in lactate modulation is under investigation as a potential mechanistic approach as a novel cancer therapy. Compound 18n is active in vitro and induces the expected pharmacodynamic effects (lactate modulation and antitumour activity) in an in vivo model.
approved: f
ligand name: compound 18n [PMID: 34382802]
type: SyntheticOrganicLigand

NBI-921352
in ch i key: NCHSBJMSORBEAV-HXUWFJFHSA-N
comment: NBI-921352 is reported as a NaV1.6 (SCN8A) selective sodium channel inhibitor that is proposed for antiepileptic activity <Reference id=42988/>. It is a clinical candidate for the treatment of patients with SCN8A developmental and epileptic encephalopathy syndrome (SCN8A-DEE). NBI-921352 was originally developed by Xenon Pharmaceuticals (and known as XEN901) <Reference id=42989/> and is now being progressed by Neurocrine Biosciences.
iupac name: (3R)-1-benzyl-N-{5-fluoro-2-methyl-4-[(1,3-thiazol-4-yl)methanesulfonyl]phenyl}-N-methylpyrrolidin-3-amine
synonym: NBI921352
synonym: XEN901
synonym: XEN-901
approved: f
ligand name: NBI-921352
type: SyntheticOrganicLigand

compound 4f [PMID: 34328319]
in ch i key: AKBHYCHPWZPGAH-QGGXVJLZSA-N
in ch i: InChI=1S/C18H21ClN2O4/c1-11-2-3-12(4-15(11)19)9-24-14-7-21(8-14)16(22)13-5-18(6-13)10-25-17(23)20-18/h2-4,13-14H,5-10H2,1H3,(H,20,23)/t13-,18+
comment: Compound 4f is a potent and reversible monoacylglycerol lipase (MAGL) inhibitor <Reference id=42987/>. In the brain, MAGL is the primary enzyme that degrades the endocannabinoid 2-arachidonoylglycerol (2-AG) to arachidonic acid (AA) and glycerol. Inhibition of MAGL (to increase 2-AG and reduce AA) is being investigated for therapeutic potential in a range of neuroinflammatory type diseases. Compound 4f is useful because it is reversible, it can cross the blood-brain barrier, and it induces the expected pharmacodynamic effects in in vivo models.
iupac name: 2-[3-[(3-chloro-4-methylphenyl)methoxy]azetidine-1-carbonyl]-7-oxa-5-azaspiro[3.4]octan-6-one
approved: f
ligand name: compound 4f [PMID: 34328319]
type: SyntheticOrganicLigand

BAY-8400
in ch i key: ATKHYZXUMVNCIO-UHFFFAOYSA-N
in ch i: InChI=1S/C21H17F2N5O/c22-20(23)16-8-15(10-24-11-16)14-3-4-17-18(9-14)28-19(12-25-17)26-27-21(28)13-2-1-6-29-7-5-13/h2-4,8-12,20H,1,5-7H2
comment: BAY-8400 is a potent inhibitor of DNA-dependent protein kinase (DNA-PK) <Reference id=42986/>. DNA-PK is required for DNA repair via non-homologous end joining, and is a cancer drug target.
synonym: BAY8400
synonym: compound 25 [PMID: 34428039]
approved: f
ligand name: BAY-8400
type: SyntheticOrganicLigand

azenosertib
in ch i key: OXTSYWDBUVRXFF-GDLZYMKVSA-N
in ch i: InChI=1S/C29H34N8O2/c1-4-14-36-27(38)23-19-30-28(31-21-7-9-22(10-8-21)35-17-15-34(3)16-18-35)33-26(23)37(36)24-11-6-20-12-13-29(39,5-2)25(20)32-24/h4,6-11,19,39H,1,5,12-18H2,2-3H3,(H,30,31,33)/t29-/m1/s1
comment: ZN-c3 is a potent inhibitor of WEE1 G2 checkpoint kinase (WEE1) that was developed for anti-cancer potential <Reference id=42985/>. Inhibition of Wee1 in cancer cells that rely on G2/M checkpoint regulation for survival, disrupts G2/M cell cycle arrest which leads to premature entry into mitosis, replication stress and ultimately cell death. The chemical structure of ZN-c3 matches that for the INN 'azenosertib' which was published in the WHO's proposed INN list 127 on 21 July 2022.
iupac name: 1-[(7R)-7-ethyl-7-hydroxy-5,6-dihydrocyclopenta[b]pyridin-2-yl]-6-[4-(4-methylpiperazin-1-yl)anilino]-2-prop-2-enylpyrazolo[3,4-d]pyrimidin-3-one
synonym: ZNc3
synonym: compound 16 [PMID: 34423975]
synonym: ZN-c3
approved: f
ligand name: azenosertib
type: SyntheticOrganicLigand

TAK-020
in ch i key: HIMUHMBGRATXMK-LBPRGKRZSA-N
in ch i: InChI=1S/C18H17N5O3/c1-2-15(24)23-8-7-12(10-23)26-17-13-6-4-3-5-11(13)9-14(19-17)16-20-18(25)22-21-16/h2-6,9,12H,1,7-8,10H2,(H2,20,21,22,25)/t12-/m0/s1
comment: TAK-020 is a covalent Bruton's tyrosine kinase (BTK) inhibitor <Reference id=42983/>. The compound bonds to Cys481 in BTK's ATP binding site. It was designed for potential to treat haematologic malignancies and/or autoimmune diseases.
iupac name: 3-[1-[(3S)-1-prop-2-enoylpyrrolidin-3-yl]oxyisoquinolin-3-yl]-1,4-dihydro-1,2,4-triazol-5-one
synonym: TAK020
synonym: compound 3 [PMID: 34448571]
approved: f
ligand name: TAK-020
type: SyntheticOrganicLigand

MK-8262
in ch i key: VYZPBLVSILOWMJ-YTCPBCGMSA-N
in ch i: InChI=1S/C35H25F9N2O5/c1-16-9-17(31(47)48)3-5-23(16)19-12-26(30(50-2)45-15-19)24-6-4-20(33(36,37)38)14-25(24)27-7-8-28-29(51-32(49)46(27)28)18-10-21(34(39,40)41)13-22(11-18)35(42,43)44/h3-6,9-15,27-29H,7-8H2,1-2H3,(H,47,48)/t27-,28-,29+/m0/s1
comment: MK-8262 is a small molecule that inhibits cholesterylester transfer protein (CETP; P11597) <Reference id=42982/>. It was developed as a best-in-class back-up clinical candidate to <Ligand id=8400/>, but like anacetrapib its development was discontinued. CETP was considered as a target for prevention of dyslipidemia and reducing cardiovascular mortality, with CETP inhibitors proposed as a direct route to raise HDL. Clinical trial results for a number of CETP inhibitors have failed to show clinical benefit. Failed candidates in addition to this one, include <Ligand id=8401/>, anacetrapib, torcetrapib, and dalcetrapib <Reference id=42981/>.
iupac name: 4-[5-[2-[(1R,5S,7aS)-1-[3,5-bis(trifluoromethyl)phenyl]-3-oxo-5,6,7,7a-tetrahydro-1H-pyrrolo[1,2-c][1,3]oxazol-5-yl]-4-(trifluoromethyl)phenyl]-6-methoxypyridin-3-yl]-3-methylbenzoic acid
synonym: MK8262
synonym: compound 87 ]PMID: 34375108]
approved: f
ligand name: MK-8262
type: SyntheticOrganicLigand

12-Imidazolyl-1-dodecanol
canonical SMILES: OCCCCCCCCCCCCc1ncc[nH]1
isomeric SMILES: OCCCCCCCCCCCCc1ncc[nH]1
in ch i key: DOKOVZHOVUEIBQ-UHFFFAOYSA-N
in ch i: InChI=1S/C15H28N2O/c18-14-10-8-6-4-2-1-3-5-7-9-11-15-16-12-13-17-15/h12-13,18H,1-11,14H2,(H,16,17)
comment: A rationally designed lead compound that provides evidence of the prospect of targeting CYP2E1 for the treatment of alcoholic steatohepatitis (ASH) <Reference id=41108/>.
iupac name: 12-(1H-imidazol-2-yl)dodecan-1-ol
approved: f
ligand name: 12-Imidazolyl-1-dodecanol
type: SyntheticOrganicLigand

BMS-986318
in ch i key: WPGAVSDZYIRUGE-UHFFFAOYSA-N
comment: BMS-986318 is a nonbile acid farnesoid X receptor (FXR) agonist that was developed as a potential therapeutic for nonalcoholic steatohepatitis <Reference id=42970/>.
synonym: BMS986318
synonym: compound 1 [PMID: 34531950]
approved: f
ligand name: BMS-986318
type: SyntheticOrganicLigand

ASTX029
in ch i key: BVRGQPJKSKKGIH-PUAOIOHZSA-N
comment: ASTX029 is an orally bioavailable, clinical stage inhibitor of ERK1/2 kinases <Reference id=42968/>. It was designed to inhibit the mitogen-activated protein kinase pathway in cancer cells. ASTX029 suppresses both ERK phosphorylation and enzymatic activity <Reference id=42969/>.
synonym: ASTX-029
synonym: compound 15 [PMID: 34387469]
approved: f
ligand name: ASTX029
type: SyntheticOrganicLigand

compound 20 [PMID: 34432979]
in ch i key: CHNBEZLJAQUZEX-LFRONEFISA-N
comment: Compound 20 is a PROTAC that targets receptor-interacting serine/threonine protein kinase 2 (RIPK2) for degradation <Reference id=42967/>. It promotes RIPK2 degradation by promoting the formation of a ternary complex between an E3 ligase (in this case an inhibitor of apoptosis (IAP) E3 ligase) and the target protein. Compound 20 inhibits TNFα release which is indicative of inhibition of RIPK2-induced transcriptional activation of inflammatory cytokine genes.
approved: f
ligand name: compound 20 [PMID: 34432979]
type: SyntheticOrganicLigand

MD-222
in ch i key: RRSNDVCODIMOFX-MPKOGUQCSA-N
comment: MD-222 is a proteolysis targeting chimera (PROTAC) agent that induces degradation of the human murine double minute 2 (MDM2) protein <Reference id=42964/>. MDM2 is a crucial cellular inhibitor of the tumour suppressor p53, and is an oncology drug target. MD-222 simultaneously binds to MDM2 and cereblon, bringing the target protein into the proximity of the ubiquitination zone of the E3 ligase.
xref: CHEMBL4436772
synonym: compound 13 [PMID: 30525597]
synonym: MD222
approved: f
ligand name: MD-222
type: SyntheticOrganicLigand

MG-277
in ch i key: BANRYGZZIMCKNA-OYGJEQPESA-N
comment: MG-277 is a molecular glue type protein degrader <Reference id=42963/>. It is a structurally modified analogue of MD-222 which is a MDM2 PROTAC degrader. The cereblon-binding moiety MG-277 is required for its growth inhibitory effects on cancer cells. MG-277 achieves its potent anticancer activity by inducing degradation of the translation termination factor GSPT1 (a.k.a. eRF3a; GSPT1; P15170), and this is independent of MDM2.
xref: CHEMBL4449512
synonym: MG277
approved: f
ligand name: MG-277
type: SyntheticOrganicLigand

BRD7929
in ch i key: VKRCTZCBMKVHCK-RTOKGZNSSA-N
in ch i: InChI=1S/C33H38N4O2/c1-35(2)23-30-32(27-15-13-26(14-16-27)12-11-25-9-5-4-6-10-25)31-24-36(21-7-8-22-37(30)31)33(38)34-28-17-19-29(39-3)20-18-28/h4-6,9-10,13-20,30-32H,7-8,21-24H2,1-3H3,(H,34,38)/t30-,31+,32+/m1/s1
comment: BRD7929 is an advanced analogue from a bicyclic azetidine series of antimalarial compounds <Reference id=33471/>. The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
iupac name: (8R,9S,10S)-10-[(dimethylamino)methyl]-N-(4-methoxyphenyl)-9-[4-(2-phenylethynyl)phenyl]-1,6-diazabicyclo[6.2.0]decane-6-carboxamide
xref: CHEMBL4284340
approved: f
ligand name: BRD7929
type: SyntheticOrganicLigand

DT2216
in ch i key: PXVFFBGSTYQHRO-REQIQPEASA-N
comment: DT2216 is a clinical stage PROTAC type protein degarder. It targets the BCL-XL protein (an anti-apoptotic protein that is overexpressed by some cancers) for degradation via the Von Hippel-Lindau (VHL) E3 ligase, and was developed for potential antitumour activity <Reference id=42955/><Reference id=42956/>. In vivo (in mice), The target protein binding moiety is based on the BCL-XL protein antagonist <Ligand id=8319/> (ABT-263) <Reference id=42955/>. Since VHL is poorly expressed in platelets, DT2216 is significantly less toxic to platelets than parental navitoclax.
iupac name: (2S,4R)-1-[(2S)-2-[[7-[4-[(3R)-3-[4-[[4-[4-[[2-(4-chlorophenyl)-5,5-dimethylcyclohexen-1-yl]methyl]piperazin-1-yl]benzoyl]sulfamoyl]-2-(trifluoromethylsulfonyl)anilino]-4-phenylsulfanylbutyl]piperazin-1-yl]-7-oxoheptanoyl]amino]-3,3-dimethylbutanoyl]-4-hydroxy-N-[(1S)-1-[4-(4-methyl-1,3-thiazol-5-yl)phenyl]ethyl]pyrrolidine-2-carboxamide
synonym: DT-2216
approved: f
ligand name: DT2216
type: SyntheticOrganicLigand

S-deschloroketamine
canonical SMILES: CNC1(CCCCC1=O)c1ccccc1
isomeric SMILES: CNC1(CCCCC1=O)c1ccccc1
in ch i key: ZAGBSZSITDFFAF-UHFFFAOYSA-N
in ch i: InChI=1S/C13H17NO/c1-14-13(10-6-5-9-12(13)15)11-7-3-2-4-8-11/h2-4,7-8,14H,5-6,9-10H2,1H3
comment: This is the S enantiomer of the <Ligand id=4233/> analogue deschloroketamine (DCK). The pharmacodynamics and pharmacokinetics of S-DCK (in rats) in comparision to ketamine were reported by Štefková-Mazochová et al. (2021) <Reference id=42993/>. In summary, S-DCK exhibits similar behavioural, addictive and PK profiles as ketamine, but it has a longer duration of action.
iupac name: (2S)-2-(methylamino)-2-phenylcyclohexan-1-one
synonym: S-DCK
approved: f
ligand name: S-deschloroketamine
type: SyntheticOrganicLigand

vanin-1 inhibitor [PMID: 33196323]
isomeric SMILES: O=C(c1cc(ccc1)C#N)c1cnc(NC2(CC2)c2cncnc2)nc1
in ch i key: OJUWWGHSEBTYGS-UHFFFAOYSA-N
in ch i: InChI=1S/C19H14N6O/c20-7-13-2-1-3-14(6-13)17(26)15-8-23-18(24-9-15)25-19(4-5-19)16-10-21-12-22-11-16/h1-3,6,8-12H,4-5H2,(H,23,24,25)
comment: This vanin 1 inhibitor was claimed (as Example 1) in Pfizer's patent WO2016193844A1 <Reference id=42939/>, and the structure was disclosed in a peer reviewed publication in 2021 <Reference id=42940/>. Blocking the pantetheinase activity of vanin 1 did not provide the hypothesised protective effect in models of acute and chronic kidney disease.
iupac name: 3-[2-[(1-pyrimidin-5-ylcyclopropyl)amino]pyrimidine-5-carbonyl]benzonitrile
synonym: example 1 [WO2016193844A1]
approved: f
ligand name: vanin-1 inhibitor [PMID: 33196323]
type: SyntheticOrganicLigand

BI1265162
canonical SMILES: CCn1c(CNC(=O)c2nc(Cl)cnc2N)[n+](c2c1cc(OCC(=O)NCCOCP(=O)(C)C)cc2)CC
isomeric SMILES: CCn1c(CNC(=O)c2nc(Cl)cnc2N)[n+](CC)c2ccc(OCC(=O)NCCOCP(=O)(C)C)cc12
in ch i key: DXVNYGRCASBPNU-UHFFFAOYSA-O
comment: We obtained this structure from a list compiled by DrugHunter of first time disclosures made at the 2021 XXVI EFMC International Symposium on Medicinal Chemistry (EFMC-ISMC). The structure mapped to a PubChem entry that was submitted by SureChEMBL in 2017 as an extraction from Bohringer Ingelhiem's patent WO2017028927A1 <Reference id=42938/>. The EFMC-ISMC discosure provided the BI1265162 name-to-structure association. BI1265162 was developed as an inhibitor of the endothelial sodium channel (ENaC), whose excessive activity in cystic fibrosis contributes to the production of hyperconcentrated mucus <Reference id=42937/>. It is described as a 'direct inhibitor' of ENaC in a review by Mall (2020) <Reference id=42937/>.
iupac name: 3-amino-6-chloro-N-[[5-[2-[2-(dimethylphosphorylmethoxy)ethylamino]-2-oxoethoxy]-1,3-diethylbenzimidazol-1-ium-2-yl]methyl]pyrazine-2-carboxamide
synonym: BI-1265162
synonym: example 2.04 [WO2017028927A1]
approved: f
ligand name: BI1265162
type: SyntheticOrganicLigand

TCN-213
canonical SMILES: O=C(CSc1nnc(s1)NCc1ccccc1)NCC1CCCCC1
isomeric SMILES: C1CCC(CC1)CNC(=O)CSc1nnc(s1)NCc1ccccc1
in ch i key: XBAZPYFIYYCZBO-UHFFFAOYSA-N
in ch i: InChI=1S/C18H24N4OS2/c23-16(19-11-14-7-3-1-4-8-14)13-24-18-22-21-17(25-18)20-12-15-9-5-2-6-10-15/h2,5-6,9-10,14H,1,3-4,7-8,11-13H2,(H,19,23)(H,20,21)
comment: TCN-213 is a GluN2A-selective, glycine-dependent NMDA receptor allosteric inhibitor <Reference id=22926/>.
iupac name: 2-[[5-(benzylamino)-1,3,4-thiadiazol-2-yl]sulfanyl]-N-(cyclohexylmethyl)acetamide
synonym: TCN213
synonym: TCN 213
approved: f
ligand name: TCN-213
type: SyntheticOrganicLigand

AZD4604
in ch i key: JNUZADQZHYFJGW-JOCHJYFZSA-N
comment: This is a Janus kinase 1 (JAK1) inhibitor whose chemical structure was claimed in example 35 in Astrazeneca's patent WO2018134213A1 <Reference id=42933/>. A first time disclosure made at the 2021 XXVI EFMC International Symposium on Medicinal Chemistry (EFMC-ISMC) provided the AZD4604 name-to-structure association. AZD4604 is delivered by inhalation, and is proposed for anti-inflammatory action as an asthma therapy.
iupac name: (2R)-N-[3-[5-fluoro-2-(2-fluoro-3-methylsulfonylanilino)pyrimidin-4-yl]-1H-indol-7-yl]-3-methoxy-2-(4-methylpiperazin-1-yl)propanamide
xref: CHEMBL4447181
synonym: AZD-4604
synonym: Jak1-IN-7
synonym: example 35 [WO2018134213A1]
approved: f
ligand name: AZD4604
type: SyntheticOrganicLigand

AZD7624
in ch i key: NNKPHNTWNILINE-UHFFFAOYSA-N
in ch i: InChI=1S/C27H30FN5O3/c1-17-21(28)15-18(25(34)31-19-7-8-19)16-22(17)33-13-11-30-24(26(33)35)32-27(9-10-27)20-5-3-4-6-23(20)36-14-12-29-2/h3-6,11,13,15-16,19,29H,7-10,12,14H2,1-2H3,(H,30,32)(H,31,34)
comment: AZD7624 is a p38α MAPK inhibitor <Reference id=42928/>. It was designed as an inhalable agent to provide local anti-inflammatory action in inflammatory lung conditions <Reference id=42927/><Reference id=42929/>.
synonym: AZD-7624
synonym: Example 259 [WO2009001132]
approved: f
ligand name: AZD7624
type: SyntheticOrganicLigand

β-secretase inhibitor IV
in ch i key: VPNIQGRFZCTBEZ-SPTGULJVSA-N
in ch i: InChI=1S/C31H38N4O5S/c1-21(23-12-8-5-9-13-23)33-30(37)24-17-25(19-27(18-24)35(2)41(3,39)40)31(38)34-28(16-22-10-6-4-7-11-22)29(36)20-32-26-14-15-26/h4-13,17-19,21,26,28-29,32,36H,14-16,20H2,1-3H3,(H,33,37)(H,34,38)/t21-,28+,29-/m1/s1
comment: This is a small molecule inhibitor of β-secretase enzymes that is used as a standard tool in biological experiments <Reference id=42926/>.
iupac name: 3-N-[(2S,3R)-4-(cyclopropylamino)-3-hydroxy-1-phenylbutan-2-yl]-5-[methyl(methylsulfonyl)amino]-1-N-[(1R)-1-phenylethyl]benzene-1,3-dicarboxamide
xref: CHEMBL378225
synonym: compound 24 [PMID: 17432843]
approved: f
ligand name: β-secretase inhibitor IV
type: SyntheticOrganicLigand

AZD0284
in ch i key: QYYZXEPEVBXNNA-QGZVFWFLSA-N
comment: AZD0284 is an orally bioavailable inverse agonist of retinoic acid receptor-related orphan receptor C2 (NR1F3; RORγt) <Reference id=42923/>. It is proposed for anti-inflammatory potential, principally as a treatment for psoriasis.
synonym: AZD-0284
synonym: compound 20 [PMID: 34464130]
approved: f
ligand name: AZD0284
type: SyntheticOrganicLigand

asundexian
in ch i key: XYWIPYBIIRTJMM-IBGZPJMESA-N
comment: Asundexian (BAY 2433334) is a small molecule, orally administered coagulation factor XIa inhibitor. It was developed as a novel anti-thrombotic.
iupac name: 4-[[(2S)-2-[4-[5-chloro-2-[4-(trifluoromethyl)triazol-1-yl]phenyl]-5-methoxy-2-oxopyridin-1-yl]butanoyl]amino]-2-fluorobenzamide
synonym: BAY 2433334
synonym: BAY2433334
synonym: example 235 [WO2017005725A1]
approved: f
ligand name: asundexian
type: SyntheticOrganicLigand

compound 1 [PMID: 33929818]
in ch i key: PFICVJYRZDMEIX-UHFFFAOYSA-N
in ch i: InChI=1S/C27H27FN6O2/c1-17-8-22(34-7-6-27(16-29,25(34)36)26(2)4-5-26)12-23(32-17)24(35)30-13-18-9-19(11-21(28)10-18)20-14-31-33(3)15-20/h8-12,14-15H,4-7,13H2,1-3H3,(H,30,35)
iupac name: 4-[3-cyano-3-(1-methylcyclopropyl)-2-oxopyrrolidin-1-yl]-N-[[3-fluoro-5-(1-methylpyrazol-4-yl)phenyl]methyl]-6-methylpyridine-2-carboxamide
approved: f
ligand name: compound 1 [PMID: 33929818]
type: SyntheticOrganicLigand

maralixibat
in ch i key: STPKWKPURVSAJF-LJEWAXOPSA-N
in ch i: InChI=1S/C40H56N3O4S/c1-5-7-19-40(20-8-6-2)30-48(45,46)37-18-15-34(41(3)4)27-36(37)38(39(40)44)33-13-16-35(17-14-33)47-29-32-11-9-31(10-12-32)28-43-24-21-42(22-25-43)23-26-43/h9-18,27,38-39,44H,5-8,19-26,28-30H2,1-4H3/q+1/t38-,39-/m1/s1
comment: This is the parent molecule of maralixibat chloride as described in the INN. Maralixibat (LUM001) is a clinical stage, orally administered ileal bile acid transporter (IBAT; SLC10A2) inhibitor <Reference id=42911/>. It was developed for therapeutic potential to treat cholestatic pruritus.
xref: CHEMBL363392
synonym: lopixibat (deleted INN)
synonym: LUM001
synonym: LUM-001
synonym: LUM 001
synonym: compound 74 [PMID: 16134951]
synonym: Livmarli®
approved: t
ligand name: maralixibat
type: SyntheticOrganicLigand

SHA 68R
in ch i key: SFRQIPRTNYHJHP-HSZRJFAPSA-N
in ch i: InChI=1S/C26H24FN3O3/c27-22-13-11-19(12-14-22)17-28-24(31)29-15-16-30-23(18-29)26(33-25(30)32,20-7-3-1-4-8-20)21-9-5-2-6-10-21/h1-14,23H,15-18H2,(H,28,31)/t23-/m1/s1
comment: This is the (R) enantiomer of the neuropeptide S receptor 1 (NPSR1) antagonist <Ligand id=5813/>. It was identified as being the more active isomer <Reference id=42906/>. SHA 68R has been used to validate NPSR1 as a nonhormonal endometriosis therapeutic target.
iupac name: (8aR)-N-[(4-fluorophenyl)methyl]-3-oxo-1,1-diphenyl-5,6,8,8a-tetrahydro-[1,3]oxazolo[3,4-a]pyrazine-7-carboxamide
xref: CHEMBL1765703
approved: f
ligand name: SHA 68R
type: SyntheticOrganicLigand

compound 6c [PMID: 34435786]
canonical SMILES: CNc1ncnc2c1ncn2[C@@H]1SC[C@H]([C@H]1O)N
in ch i key: MEYWNRDHEXYZIX-VISXPRAWSA-N
in ch i: InChI=1S/C10H14N6OS/c1-12-8-6-9(14-3-13-8)16(4-15-6)10-7(17)5(11)2-18-10/h3-5,7,10,17H,2,11H2,1H3,(H,12,13,14)/t5-,7-,10-/m1/s1
comment: Compound 6c is an A3 adenosine receptor agonist <Reference id=42904/>.
iupac name: ((2R,3R,4S)-4-Amino)-2-(6-(methylamino)-9H-purin-9-yl)tetrahydrothiophen-3-ol
approved: f
ligand name: compound 6c [PMID: 34435786]
type: SyntheticOrganicLigand

fomepizole
canonical SMILES: Cc1c[nH]nc1
isomeric SMILES: Cc1c[nH]nc1
in ch i key: RIKMMFOAQPJVMX-UHFFFAOYSA-N
in ch i: InChI=1S/C4H6N2/c1-4-2-5-6-3-4/h2-3H,1H3,(H,5,6)
comment: Fomepizole is an alcohol dehydrogenase inhibitor.
iupac name: 4-methyl-1H-pyrazole
xref: CHEMBL1308
synonym: 4-methylpyrazole
synonym: Antizol®
approved: t
ligand name: fomepizole
type: SyntheticOrganicLigand

MMV688533
in ch i key: GGTONGQHYUQSBR-UHFFFAOYSA-N
in ch i: InChI=1S/C24H15F6N5O2/c25-23(26,27)16-10-14(9-15(12-16)20(36)35-22(31)32)5-4-13-6-7-18(24(28,29)30)17(11-13)21(37)34-19-3-1-2-8-33-19/h1-3,6-12H,(H,33,34,37)(H4,31,32,35,36)
comment: MMV688533 is the optimized lead from the acylguanidine series of antimalarial compounds <Reference id=42581/>. The compound has progressed to clinical evaluation and was awarded MMV Project of the Year (2017). The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
iupac name: 5-[2-[3-(diaminomethylidenecarbamoyl)-5-(trifluoromethyl)phenyl]ethynyl]-N-pyridin-2-yl-2-(trifluoromethyl)benzamide
synonym: SAR121
synonym: MMV533
synonym: SAR441121
approved: f
ligand name: MMV688533
type: SyntheticOrganicLigand

L-45
in ch i key: MSFPLTWUFWOKBX-IFXJQAMLSA-N
in ch i: InChI=1S/C21H24N6/c1-14(19(26(3)4)16-10-6-5-7-11-16)22-20-17-12-8-9-13-18(17)21-24-23-15(2)27(21)25-20/h5-14,19H,1-4H3,(H,22,25)/t14-,19+/m0/s1
comment: L-45 is a triazolopthalazine-based p300/CBP-associated factor (PCAF) inhibitor <Reference id=42729/>. The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
iupac name: (1S,2S)-1-N,1-N-dimethyl-2-N-(3-methyl-[1,2,4]triazolo[3,4-a]phthalazin-6-yl)-1-phenylpropane-1,2-diamine
xref: CHEMBL4570969
synonym: L-Moses
approved: f
ligand name: L-45
type: SyntheticOrganicLigand

CDD-1976
in ch i key: IXTRHVKNNCAPDT-UHFFFAOYSA-N
in ch i: InChI=1S/C18H17N3O3/c1-21(2)18(23)11-24-17-7-6-12(8-13(17)10-22)14-4-3-5-16-15(14)9-19-20-16/h3-10H,11H2,1-2H3,(H,19,20)
comment: CDD-1976 is a small molecule, reversible covalent inhibitor of the main protease (Mpro, or 3CL pro) of SARS-CoV-2 <Reference id=42780/>. It has been optimised for target selectivity and metabolic stability.
iupac name: 2-[2-formyl-4-(1H-indazol-4-yl)phenoxy]-N,N-dimethylacetamide
synonym: CDD1976
approved: f
ligand name: CDD-1976
type: SyntheticOrganicLigand

UAWJ9-36-3
in ch i key: KXNVRILCTPCDNL-VMXHOPILSA-N
in ch i: InChI=1S/C23H31N3O5/c1-23(2)17-11-26(22(30)31-13-14-6-4-3-5-7-14)19(18(17)23)21(29)25-16(12-27)10-15-8-9-24-20(15)28/h3-7,15-19,27H,8-13H2,1-2H3,(H,24,28)(H,25,29)/t15-,16-,17-,18-,19-/m0/s1
comment: UAWJ9-36-3 is a broad-spectrum coronavirus main protease (Mpro) inhibitor <Reference id=42779/>. It was developed by analysing the overlapping binding conformations of the peptidomimetic viral serine protease inhibitors <Ligand id=10883/>, <Ligand id=7871/>, and <Ligand id=7876/> within the Mpro from SARS-CoV-2.
iupac name: benzyl (1R,2S,5S)-2-[[(2S)-1-hydroxy-3-[(3S)-2-oxopyrrolidin-3-yl]propan-2-yl]carbamoyl]-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-3-carboxylate
approved: f
ligand name: UAWJ9-36-3
type: SyntheticOrganicLigand

amdizalisib
in ch i key: WKDBRCUUDXLTIM-NSHDSACASA-N
in ch i: InChI=1S/C19H15ClN8/c1-11(26-19-14(8-21)18(22)24-10-25-19)13-7-16-23-9-15(20)28(16)27-17(13)12-5-3-2-4-6-12/h2-7,9-11H,1H3,(H3,22,24,25,26)/t11-/m0/s1
comment: We obtained the chemical structure for amdizalisib from WHO Proposed list 125 of July 2021. This mapped to PubChem CID 118981804. Amdizalisib is one of the PI3Kδ/γ inhibitors in <Reference id=36576/>, and it is also claimed in Hutchison Medipharma's patent WO2016045591A1 <Reference id=42716/>. Hutchison Medipharma's pipeline page lists one PI3Kδ lead agent, HMPL-689, but the name>structure has not been formally disclosed, so is speculative and made in good faith.
iupac name: 4-amino-6-[[(1S)-1-(3-chloro-6-phenylimidazo[1,2-b]pyridazin-7-yl)ethyl]amino]pyrimidine-5-carbonitrile
xref: CHEMBL4438249
synonym: compound 28 [PMID: 30582813]
synonym: compound 4 [WO2016045591A1]
approved: f
ligand name: amdizalisib
type: SyntheticOrganicLigand

obefazimod
canonical SMILES: Clc1cccc2c1nc(cc2)Nc1ccc(cc1)OC(F)(F)F
isomeric SMILES: Clc1cccc2ccc(nc12)Nc1ccc(cc1)OC(F)(F)F
in ch i key: OZOGDCZJYVSUBR-UHFFFAOYSA-N
comment: We obtained the chemical structure for obefazimod from WHO Proposed list 125 of July 2021. This mapped to PubChem CID 49846599, with the association to ABX464, a first-in-class, clinical-stage, oral small molecule immunomodulator <Reference id=42714/>. ABX464 was originally developed for antiviral potential (associated via ChEMBL to the Medicines for Malaria Venture (MMV) compound MMV1581032), but was redeployed for chronic inflammatory diseases because of its potent anti-inflammatory effects in preclinical testing. ABX464 is reported to bind to the RNA cap-binding complex, which modulates both viral and cellular RNA biogenesis <Reference id=43508/>.
iupac name: 8-chloro-N-[4-(trifluoromethoxy)phenyl]quinolin-2-amine
xref: CHEMBL4297344
synonym: ABX-464
synonym: ABX464
synonym: SPL-464
synonym: MMV1581032
approved: f
ligand name: obefazimod
type: SyntheticOrganicLigand

compound 11d [PMID: 34406006]
in ch i key: NZSQBRZWARZNQH-ZWOACCQCSA-N
in ch i: InChI=1S/C33H53NO5/c1-19(35)21-11-16-33(27(36)37)18-17-31(5)22(26(21)33)9-10-24-30(4)14-13-25(39-28(38)34-20-7-8-20)29(2,3)23(30)12-15-32(24,31)6/h19-26,35H,7-18H2,1-6H3,(H,34,38)(H,36,37)/t19-,21-,22?,23?,24?,25+,26?,30-,31+,32+,33-/m0/s1
comment: Compound 11d is a betulinic acid-derived G protein-coupled bile acid receptor 1 (GPBAR1, a.k.a. TGR5) agonist <Reference id=42703/>. It was used experimentally as 11d-sodium to increase its solubility. 11d is inactive at FXR, which indicates good selectivity toward GPBAR1. In vivo, 11d produced very limited glucose-lowering effects (determined using the oral glucose tolerance test) in wild-type mice, but did induce the desired glucose-lowering effect in mice expressing a receptor with a humanising amino acid substitution (mTGR5H88Y).
iupac name: (1R,3aS,5aR,5bR,9R,11aR)-9-((Cyclopropylcarbamoyl)oxy)-1-((S)-1-hydroxyethyl)-5a,5b,8,8,11a-pentamethylicosahydro-3aH-cyclopenta[a]chrysene-3a-carboxylate
approved: f
ligand name: compound 11d [PMID: 34406006]
type: SyntheticOrganicLigand

XYT528B
in ch i key: XQYINMZHVRUGDM-LSPHDCIISA-N
in ch i: InChI=1S/C34H56O4/c1-9-10-27(35)38-26-15-16-31(6)24(30(26,4)5)14-17-33(8)25(31)12-11-23-28-22(21(2)3)13-18-34(28,29(36)37)20-19-32(23,33)7/h21-26,28H,9-20H2,1-8H3,(H,36,37)/t22-,23+,24?,25+,26+,28+,31-,32+,33+,34-/m0/s1
comment: XYT528B is a betulinic acid-derived G protein-coupled bile acid receptor 1 (GPBAR1, a.k.a. TGR5) agonist <Reference id=42704/><Reference id=42703/>. It exhibits species difference with respect to GPBAR1 activation, with nM potency at the human and canine receptors, but lower μM potency at the mouse receptor. XYT528B has almost no activity in in vivo mouse models.
approved: f
ligand name: XYT528B
type: SyntheticOrganicLigand

HTL6641
in ch i key: SUQZCEUKWPKXEE-UHFFFAOYSA-N
comment: HTL6641 is a small molecule dual orexin receptor antagonist (DORA) <Reference id=42701/>. This class of compounds includes the approved insomnia drugs <Ligand id=2890/> and <Ligand id=9302/>.
iupac name: 2-(5,6-dimethoxypyridin-3-yl)-1,1-dioxo-4-[(2,4,6-trifluorophenyl)methyl]pyrido[2,3-e][1,2,4]thiadiazin-3-one
xref: CHEMBL3740099
synonym: HTL-6641
synonym: HTL'641
synonym: compound 27 [Christopher et al., 2015]
approved: f
ligand name: HTL6641
type: SyntheticOrganicLigand

SRI22141
in ch i key: AQMQWKFSMIRRJA-OGICNVKRSA-N
in ch i: InChI=1S/C35H33ClN2O3/c1-38-16-15-34-30-24-11-14-28(39)32(30)41-33(34)31-25(18-26(21-37-31)23-9-12-27(36)13-10-23)20-35(34,29(38)19-24)40-17-5-8-22-6-3-2-4-7-22/h2-4,6-7,9-14,18,21,29,33,39H,5,8,15-17,19-20H2,1H3/t29-,33+,34+,35-/m1/s1
comment: SRI22141 is a dual μ/δ opioid receptor agonist <Reference id=42700/>. It was designed as a tool to determine if dual μ/δ agonism could offer a therapeutic option for neuropathic pain, with reduced side effects (re. tolerance and addiction liabilities) compared to traditional μ agonists.
xref: CHEMBL2179656
synonym: SRI-22141
synonym: SRI 22141
approved: f
ligand name: SRI22141
type: SyntheticOrganicLigand

PF-514273
in ch i key: FJMQJSUOOGOWBD-UHFFFAOYSA-N
comment: PF-514273 has activity as a cannabinoid 1 (CB1) receptor antagonist <Reference id=42699/>.
iupac name: 2-(2-chlorophenyl)-3-(4-chlorophenyl)-7-(2,2-difluoropropyl)-5,6-dihydropyrazolo[3,4-f][1,4]oxazepin-8-one
xref: CHEMBL484929
synonym: PF 514273
synonym: PF514273
synonym: compound 19d [PMID: 19351113]
approved: f
ligand name: PF-514273
type: SyntheticOrganicLigand

adaptavir
in ch i key: AKWRNBWMGFUAMF-ZESMOPTKSA-N
in ch i: InChI=1S/C35H56N10O15/c1-13(36)29(54)41-22(12-46)32(57)43-26(16(4)49)34(59)45-27(17(5)50)35(60)44-25(15(3)48)33(58)40-21(11-23(37)52)30(55)39-20(10-18-6-8-19(51)9-7-18)31(56)42-24(14(2)47)28(38)53/h6-9,13-17,20-22,24-27,46-51H,10-12,36H2,1-5H3,(H2,37,52)(H2,38,53)(H,39,55)(H,40,58)(H,41,54)(H,42,56)(H,43,57)(H,44,60)(H,45,59)/t13-,14-,15-,16-,17-,20+,21+,22+,24+,25+,26+,27+/m1/s1
comment: Adaptavir (DAPTA; RAP101) is a potent and selective CCR5 antagonist <Reference id=42698/>. It acts as an HIV entry inhibitor.
xref: CHEMBL181276
synonym: DAPTA
synonym: D-Ala-peptide T-amide
approved: f
ligand name: adaptavir
type: PeptideLigand

ICI-199441
in ch i key: AEJOEPSMZCEYJN-HXUWFJFHSA-N
in ch i: InChI=1S/C21H24Cl2N2O/c1-24(21(26)14-16-9-10-18(22)19(23)13-16)20(15-25-11-5-6-12-25)17-7-3-2-4-8-17/h2-4,7-10,13,20H,5-6,11-12,14-15H2,1H3/t20-/m1/s1
comment: ICI-199441 is a κ opioid receptor agonist <Reference id=42695/>.
iupac name: 2-(3,4-dichlorophenyl)-N-methyl-N-[(1S)-1-phenyl-2-pyrrolidin-1-ylethyl]acetamide
xref: CHEMBL38576
synonym: ICI199441
synonym: ligand 1 [PMID: 8893842]
synonym: ICI 199,441
approved: f
ligand name: ICI-199441
type: SyntheticOrganicLigand

GSK852
in ch i key: FNHHVPPSBFQMEL-HURDOVMISA-N
in ch i: InChI=1S/C24H26N2O4/c1-24(14-6-4-3-5-7-14)12-30-21-18(23(29)25-2)8-13(9-19(21)24)22(28)26-20-16-10-15(27)11-17(16)20/h3-9,15-17,20,27H,10-12H2,1-2H3,(H,25,29)(H,26,28)/t15-,16-,17+,20+,24-/m0/s1
comment: GSK852 is a potent inhibitor of bromo and extra-terminal domain (BET) proteins (e.g. BRD2-4 and BRDT). It has >1000-fold selectivity for the second bromodomain (BD2) of the proteins over their first bromodomain (BD1).
iupac name: (3S)-5-N-[(1S,5R)-3-hydroxy-6-bicyclo[3.1.0]hexanyl]-7-N,3-dimethyl-3-phenyl-2H-1-benzofuran-5,7-dicarboxamide
synonym: compound 71 [PMID: 34260229]
synonym: GSK-852
approved: f
ligand name: GSK852
type: SyntheticOrganicLigand

compound 10 [PMID: 34279934]
in ch i key: MIGCLPHEGAEITL-UHFFFAOYSA-N
in ch i: InChI=1S/C20H27NO6S/c1-5-10-26-18-15(12-22)11-17(19(21-18)27-13-20(2,3)23)14-6-8-16(9-7-14)28(4,24)25/h6-9,11,22-23H,5,10,12-13H2,1-4H3
comment: Compound 10 is an analogue of <Ligand id=2896/> <Reference id=42692/>, that was designed to deliver a gut-restricted, selective COX-2 inhibitor for potential chemoprevention of colorectal cancer. Unfortunately, residual systemic COX-2 inhibition appeared to account for the in vivo inhibition of adenoma progression and increased survival in a rodent model of COX-2-mediated colorectal cancer.
iupac name: 1-((5-(Hydroxymethyl)-3-(4-(methylsulfonyl)phenyl)-6-propoxypyridin-2-yl)oxy)-2-methylpropan-2-ol
approved: f
ligand name: compound 10 [PMID: 34279934]
type: SyntheticOrganicLigand

enitociclib
in ch i key: YZCUMZWULWOUMD-NDEPHWFRSA-N
comment: VIP152 is a clinical stage CDK9 inhibitor <Reference id=42688/>. Once weekly i.v. administration is effective in rodent xenograft models, without negative safety or tolerability issues. We were able to match the chemical structure of VIP152 to the INN enitociclib that was included in the WHO proposed INN list 126 (Jan 2022).
iupac name: 5-fluoro-4-(4-fluoro-2-methoxyphenyl)-N-[4-[(methylsulfonimidoyl)methyl]pyridin-2-yl]pyridin-2-amine
synonym: VIP-152
synonym: BAY 1251152
synonym: BAY1251152
synonym: BAY-1251152
synonym: VIP152
approved: f
ligand name: enitociclib
type: SyntheticOrganicLigand

TAK-041
in ch i key: JZGLECLGVQRPPI-NSHDSACASA-N
in ch i: InChI=1S/C18H15F3N4O3/c1-11(12-6-8-13(9-7-12)28-18(19,20)21)22-16(26)10-25-17(27)14-4-2-3-5-15(14)23-24-25/h2-9,11H,10H2,1H3,(H,22,26)/t11-/m0/s1
comment: TAK-041 is a clinical stage, orally active GPR139 agonist <Reference id=42687/>.
synonym: TAK041
synonym: NBI-1065846
synonym: NBI1065846
synonym: compound 56 [PMID: 34260228]
approved: f
ligand name: TAK-041
type: SyntheticOrganicLigand

evixapodlin
in ch i key: OIIOPWHTJZYKIL-PMACEKPBSA-N
comment: We obtained the chemical structure for evixapodlin from WHO Proposed list 125 of July 2021. The INN record describes it as a programmed cell death ligand 1 (PD-L1) inhibitor. Evixapodlin is one of the chemical structures that is claimed in Gilead Sciences' patent WO2019160882A1 (compound number 139) <Reference id=42686/>. It was developed as an alternative to monocloncal antibody PD-L1/PD-1 interaction inhibitors, for potential anticancer and antiviral activities. First disclosures at the ACS meeting in Chicago in 2022 mapped evixapodlin to Gilead's clinical lead GS-4224. GS-4224 is orally bioavailable.
iupac name: (5S)-5-[[[5-[2-chloro-3-[2-chloro-3-[6-methoxy-5-[[[(2S)-5-oxopyrrolidin-2-yl]methylamino]methyl]pyrazin-2-yl]phenyl]phenyl]-3-methoxypyrazin-2-yl]methylamino]methyl]pyrrolidin-2-one
synonym: PD-1/PD-L1-IN 7
synonym: compound 139 [WO2019160882A1]
synonym: GS-4224
synonym: GS4224
approved: f
ligand name: evixapodlin
type: SyntheticOrganicLigand

sucunamostat
in ch i key: PUZUTMLAAWVCCV-WBMJQRKESA-N
in ch i: InChI=1S/C22H22N4O8/c23-22(24)25-13-3-1-11(2-4-13)21(32)34-14-5-6-15-12(10-33-17(15)8-14)7-18(27)26-16(20(30)31)9-19(28)29/h1-6,8,12,16H,7,9-10H2,(H,26,27)(H,28,29)(H,30,31)(H4,23,24,25)/t12-,16+/m1/s1
comment: We obtained the chemical structure for sucunamostat from WHO Proposed list 125 of July 2021. The chemical structure of sucunamostat is identical to the disclosed structure of the small molecule, reversible enteropeptidase (TMPRSS15) inhibitor SCO-792 <Reference id=42683/>.
iupac name: (2S)-2-[[2-[(3S)-6-[4-(Diaminomethylideneamino)benzoyl]oxy-2,3-dihydro-1-benzofuran-3-yl]acetyl]amino]butanedioic acid
synonym: SCO792
synonym: SCO-792
approved: f
ligand name: sucunamostat
type: SyntheticOrganicLigand

zenuzolac
canonical SMILES: OC(=O)CC1ON=C(C1)c1ccccc1
isomeric SMILES: C1C(ON=C1c1ccccc1)CC(=O)O
in ch i key: MUFJHYRCIHHATF-UHFFFAOYSA-N
in ch i: InChI=1S/C11H11NO3/c13-11(14)7-9-6-10(12-15-9)8-4-2-1-3-5-8/h1-5,9H,6-7H2,(H,13,14)
comment: We obtained the chemical structure for zenuzolac from WHO Proposed list 125 of July 2021, in which it is described as an anti-inflammatory. The INN represents the racemic (rac) mixture of (R) and (S) enantiomers. We show the molecule without specified stereochemistry to represent the mixture. We have mapped this to PubChem CID 10798271. Synonyms from the PubChem entry associate the structure with research code VGX-1027 (VGX Pharmaceuticals). VGX-1027 is an immunomodulatory compound that downregulates proinflammatory cytokine production and NF-κB and MAP kinase activation <Reference id=43631/><Reference id=43630/><Reference id=42678/>. COVID-19: Zenuzolac (re-named as GLS-1027) is being evaluated to determine its potential to reduce SARS-CoV-2-induced pulmonary inflammation (pneumonitis).
xref: CHEMBL1320667
synonym: rac-[(5R)-3-phenyl-4,5-dihydro-1,2-oxazol-5-yl]acetic acid
synonym: (S,R)-3-Phenyl-4,5-dihydro-5-isoxazole acetic acid
synonym: GIT27
synonym: GIT-27
synonym: VGX-1027
synonym: VGX1027
synonym: GIT-027
synonym: GLS-1027
synonym: GLS1027
approved: f
ligand name: zenuzolac
type: SyntheticOrganicLigand

zunsemetinib
in ch i key: FQPQMJULRZINPV-UHFFFAOYSA-N
comment: We obtained the chemical structure for zunsemetinib from WHO Proposed list 125 of July 2021. This mapped to PubChem CID 86291496. The compound is claimed in Confluence Life Sciences' patent US9115089B2 as kinase inhibitor with potential to treat p38 kinase-mediated diseases <Reference id=42674/>. Confluence Life Sciences is a subsidiary of Aclaris Therapeutics. We speculate that zunsemetinib is the MAPK-activated protein kinase 2 (MK2) inhibitor ATI-450 (formerly CDD-450 <Reference id=42676/>), that is included on Aclaris' pipeline page. Phase 1 safety and tolerability of ATI-450 were reported in June 2021 <Reference id=42675/>. This article described ATI-450 as an inhibitor of p38α/MK2 pathway-mediated inflammatory signalling, but discloses only a partial chemical structure in a supplementary figure. The same incomplete chemical structure appears in <Reference id=42676/>. ATI-450 binds with high affinity to the interface of the p38MAPK-MK2 complex and selectively inhibits p38MAPK-catalysed phosphorylation of MK2 which stabilises the inactive conformation of MK2, and subsequently reduces inflammatory cytokine levels <Reference id=42676/>.
iupac name: 3-chloro-4-[(3,5-difluoropyridin-2-yl)methoxy]-1-[2-[2-(2-hydroxypropan-2-yl)pyrimidin-4-yl]-5-methylpyridin-4-yl]-6-methylpyridin-2-one
xref: CHEMBL3704901
synonym: CDD-450
synonym: CDD450
synonym: ATI-450
synonym: ATI450
approved: f
ligand name: zunsemetinib
type: SyntheticOrganicLigand

zapnometinib
canonical SMILES: Ic1ccc(c(c1)Cl)Nc1c(ccc(c1F)F)C(=O)O
isomeric SMILES: Clc1c(Nc2c(C(=O)O)ccc(c2F)F)ccc(c1)I
in ch i key: XCNBGWKQXRQKSA-UHFFFAOYSA-N
comment: We obtained the chemical structure for zapnometinib from WHO Proposed list 125 of July 2021. This mapped to PubChem CID 10112191, and via ChEMBL to the MEK serine/threonine protein kinases inhibitor PD-0184264 <Reference id=23016/>. is an oral MEK inhibitor that targets the Raf/MEK/ERK signalling pathway. This pathway is exploited (activated) by several species of RNA viruses (e.g. influenza viruses, hantaviruses, respiratory syncytial viruses and coronaviruses) for their successful replication. Blocking the host Raf/MEK/ERK signalling pathway inhibits formation of fully-formed virus particles in infected cells, and reduces viral load. At the same time, inhibiting MEK provides potential to modulate the immune response induced during infection. In COVID-19 zapnometinib is predicted to reduce expression of pro-inflammatory cytokines and/or chemokines (e.g. TNF-α, IL-1β, CXCL10/IP-10, CXCL8/IL-8, CCL2/MCP-1 and CCL3/MIP-1α) that drive the destructive hyperinflammation in patients with severe disease.
iupac name: 2-(2-chloro-4-iodoanilino)-3,4-difluorobenzoic acid
xref: CHEMBL481949
synonym: PD-0184264
synonym: PD0184264
synonym: ATR-002
synonym: ATR002
approved: f
ligand name: zapnometinib
type: SyntheticOrganicLigand

vepafestinib
canonical SMILES: COCc1ccc(cc1)NC(=O)c1c(C#CCN2CCOCC2)n(c2c1c(N)ncn2)C1(C)CC1
isomeric SMILES: Nc1c2c(ncn1)n(c(c2C(=O)Nc1ccc(cc1)COC)C#CCN1CCOCC1)C1(CC1)C
in ch i key: SFXVRNLGOSAWIV-UHFFFAOYSA-N
in ch i: InChI=1S/C26H30N6O3/c1-26(9-10-26)32-20(4-3-11-31-12-14-35-15-13-31)21(22-23(27)28-17-29-24(22)32)25(33)30-19-7-5-18(6-8-19)16-34-2/h5-8,17H,9-16H2,1-2H3,(H,30,33)(H2,27,28,29)
comment: We obtained the chemical structure for vepafestinib from WHO Proposed list 125 of July 2021. This mapped to PubChem CID 134164132. The structure was first submitted to PubChem as an extraction from a Taiho Pharmaceutical patent <Reference id=42668/>. Vepafestinib is claimed as a RET kinase inhibitor.
iupac name: 4-amino-N-[4-(methoxymethyl)phenyl]-7-(1-methylcyclopropyl)-6-(3-morpholin-4-ylprop-1-ynyl)pyrrolo[2,3-d]pyrimidine-5-carboxamide
synonym: example 85 [US20180009818A1]
approved: f
ligand name: vepafestinib
type: SyntheticOrganicLigand

vebreltinib
in ch i key: QHXLXUIZUCJRKV-UHFFFAOYSA-N
in ch i: InChI=1S/C20H15F3N8/c1-29-9-11-6-14(15(21)7-17(11)27-29)20(22,23)19-26-25-18-5-4-16(28-31(18)19)12-8-24-30(10-12)13-2-3-13/h4-10,13H,2-3H2,1H3
comment: We obtained the chemical structure for vebreltinib from WHO Proposed list 125 of July 2021. This mapped to PubChem CID 72202701. Synonyms for vebreltinib (from PubChem) include APL-101 and PLB-1001 <Reference id=42667/>. Vebreltinib is an oral, ATP-competitive MET kinase inhibitor that is active against MET-altered tumour cells in preclinical models. It can cross the blood-brain barrier.
iupac name: 6-(1-cyclopropylpyrazol-4-yl)-3-[difluoro-(6-fluoro-2-methylindazol-5-yl)methyl]-[1,2,4]triazolo[4,3-b]pyridazine
synonym: PLB1001
synonym: APL-101
synonym: bozitinib
approved: f
ligand name: vebreltinib
type: SyntheticOrganicLigand

tuxobertinib
in ch i key: HIBPKFXWOPYJPZ-UHFFFAOYSA-N
in ch i: InChI=1S/C29H29ClN6O4/c1-2-28(37)35-25-16-22-24(17-27(25)39-14-11-36-9-12-38-13-10-36)32-19-33-29(22)34-20-6-7-26(23(30)15-20)40-18-21-5-3-4-8-31-21/h2-8,15-17,19H,1,9-14,18H2,(H,35,37)(H,32,33,34)
comment: We obtained the chemical structure for tuxobertinib from WHO Proposed list 125. This mapped to PubChem CID 154824631. Tuxobertinib (BDTX-189) is an irreversible, orally active, ATP-competitive EGFR/HER2 inhibitor. It is being developed by Black Diamond Therapeutics as a therapy for cancers that are driven by oncogenic allosteric, activating mutations of the EGFR and ErbB2 (HER2). It was designed to minimize EGFR-WT mediated toxicities. Tuxobertinib is one of the examples claimed in patent US11034672B1 <Reference id=42666/>.
iupac name: N-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]-7-(2-morpholin-4-ylethoxy)quinazolin-6-yl]prop-2-enamide
synonym: BDTX-189
synonym: BDTX189
synonym: example 8 [US11034672B1]
approved: f
ligand name: tuxobertinib
type: SyntheticOrganicLigand

tunlametinib
canonical SMILES: OCCONC(=O)c1cc2scnc2c(c1Nc1ccc(cc1F)I)F
in ch i key: UFZJUVFSSINETF-UHFFFAOYSA-N
comment: We obtained the chemical structure for tunlametinib from WHO Proposed list 125 (July 2021). This mapped to PubChem CID 71621329. The chemical structure is claimed in Tianjin Binjiang Pharma's patent WO2013107283A1 for activity as a MEK inhibitor with potential to treat cancers and inflammation <Reference id=42665/>.
iupac name: 4-fluoro-5-(2-fluoro-4-iodoanilino)-N-(2-hydroxyethoxy)-1,3-benzothiazole-6-carboxamide
synonym: Example 9 [WO2013107283A1]
approved: f
ligand name: tunlametinib
type: SyntheticOrganicLigand

tizaterkib
in ch i key: HVIGNZUDBVLTLU-MRXNPFEDSA-N
in ch i: InChI=1S/C24H24F2N8O2/c1-14-9-27-24(30-20-6-7-28-32(20)2)31-21(14)19-12-33-11-16(13-36-3)34(23(35)22(33)29-19)10-15-4-5-17(25)18(26)8-15/h4-9,12,16H,10-11,13H2,1-3H3,(H,27,30,31)/t16-/m1/s1
comment: Tizaterkib (AZD0364) is a potent, selective and reversible type 1 ERK1/2 inhibitor <Reference id=42663/>.
iupac name: (6R)-7-[(3,4-difluorophenyl)methyl]-6-(methoxymethyl)-2-[5-methyl-2-[(2-methylpyrazol-3-yl)amino]pyrimidin-4-yl]-5,6-dihydroimidazo[1,2-a]pyrazin-8-one
xref: CHEMBL4482864
synonym: AZD0364
synonym: AZD-0364
synonym: ATG-017
approved: f
ligand name: tizaterkib
type: SyntheticOrganicLigand

berberine
canonical SMILES: COc1c(OC)ccc2c1c[n+]1CCc3c(c1c2)cc1c(c3)OCO1
isomeric SMILES: COc1c(OC)ccc2c1c[n+]1CCc3c(c1c2)cc1c(c3)OCO1
in ch i key: YBHILYKTIRIUTE-UHFFFAOYSA-N
in ch i: InChI=1S/C20H18NO4/c1-22-17-4-3-12-7-16-14-9-19-18(24-11-25-19)8-13(14)5-6-21(16)10-15(12)20(17)23-2/h3-4,7-10H,5-6,11H2,1-2H3/q+1
comment: Berberine is a botanical alkaloid compound that has found use in traditional medicine in some countries. It is poorly orally bioavailable and interacts adversely with prescription drugs.
xref: CHEMBL12089
synonym: umbellatine
approved: f
ligand name: berberine
type: NaturalProductLigand

sunvozertinib
in ch i key: BTMKEDDEMKKSEF-QGZVFWFLSA-N
comment: We obtained the chemical structure for sunvozertinib from WHO Proposed list 125, in which it is described as a tyrosine kinase inhibitor with proposed antineoplastic action. This mapped to PubChem CID 139377809. Sunvozertinib is one of the compounds that are claimed in Dizal (Jiangsu) Pharmaceutical's patent WO2019149164A1 as ERBB/BTK inhibitors <Reference id=42657/>.
iupac name: N-[5-[[4-[5-chloro-4-fluoro-2-(2-hydroxypropan-2-yl)anilino]pyrimidin-2-yl]amino]-2-[(3R)-3-(dimethylamino)pyrrolidin-1-yl]-4-methoxyphenyl]prop-2-enamide
synonym: Example 52 [WO2019149164A1]
approved: f
ligand name: sunvozertinib
type: SyntheticOrganicLigand

luxeptinib
in ch i key: MWHHJYUHCZWSLS-UHFFFAOYSA-N
in ch i: InChI=1S/C25H17F4N5O2/c1-11-9-30-23(32-11)16-5-4-14(17-10-31-24(35)21(16)17)15-3-2-13(8-18(15)27)33-25(36)34-22-19(28)6-12(26)7-20(22)29/h2-9H,10H2,1H3,(H,30,32)(H,31,35)(H2,33,34,36)
comment: We obtained the chemical structure for luxeptinib from WHO Proposed list 125. This mapped to PubChem CID 118480924. Luxeptinib (CG-806) is a clinical stage, oral small molecule non-covalent pan-BTK/pan-FLT3 inhibitor. The name>structure association has not been formally disclosed, but the structure is claimed in CrystalGenomics' patent US9758508B2 <Reference id=42656/>.
iupac name: 1-[3-fluoro-4-[7-(5-methyl-1H-imidazol-2-yl)-1-oxo-2,3-dihydroisoindol-4-yl]phenyl]-3-(2,4,6-trifluorophenyl)urea
xref: CHEMBL4594420
synonym: CG-806
synonym: CG806
synonym: CG-026806
synonym: CG026806
synonym: example 7 [US9758508B2]
approved: f
ligand name: luxeptinib
type: SyntheticOrganicLigand

ilunocitinib
isomeric SMILES: C1CC1S(=O)(=O)N1CC(C1)(CC#N)n1cc(cn1)c1c2cc[nH]c2ncn1
in ch i key: RVOUEXFKIYNODQ-UHFFFAOYSA-N
in ch i: InChI=1S/C17H17N7O2S/c18-5-4-17(9-23(10-17)27(25,26)13-1-2-13)24-8-12(7-22-24)15-14-3-6-19-16(14)21-11-20-15/h3,6-8,11,13H,1-2,4,9-10H2,(H,19,20,21)
comment: The chemical structure for ilunocitinib was obtained from WHO Proposed list 125. This mapped to PubChem CID 44231134. Ilunocitinib appears to be an oral JAK inhibitor that is intended for veterinary use, and which is being developed by Elanco Animal Health as a therapeutic for inflammatory skin conditions.
iupac name: 2-[1-cyclopropylsulfonyl-3-[4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]azetidin-3-yl]acetonitrile
synonym: LY3411067
synonym: LY-3411067
approved: f
ligand name: ilunocitinib
type: SyntheticOrganicLigand

alofanib
in ch i key: QUQGQIASFYWKAB-UHFFFAOYSA-N
in ch i: InChI=1S/C19H15N3O6S/c1-12-8-18(22(25)26)17(10-16(12)14-5-3-7-20-11-14)21-29(27,28)15-6-2-4-13(9-15)19(23)24/h2-11,21H,1H3,(H,23,24)
comment: Alofanib (RPT835) is an allosteric inhibitor of the receptor tyrosine kinase, fibroblast growth factor receptor 2 (FGFR2) <Reference id=42530/><Reference id=42532/><Reference id=42531/><Reference id=42533/>. It inhibits phosphorylation of FGF receptor substrate 2α (FRS2α), but does not block FGF2-FGFR2 binding. Alofanib inhibits angiogenesis and was developed for antitumour potential.
xref: CHEMBL4594436
synonym: RPT-835
synonym: RPT835
approved: f
ligand name: alofanib
type: SyntheticOrganicLigand

gunagratinib
isomeric SMILES: CNc1c(c(nn1[C@H]1CCN(C1)C(=O)C=C)C#Cc1cc(cc(c1)OC)OC)C(=O)N
in ch i key: QFUIJOBJAQBGDH-HNNXBMFYSA-N
in ch i: InChI=1S/C22H25N5O4/c1-5-19(28)26-9-8-15(13-26)27-22(24-2)20(21(23)29)18(25-27)7-6-14-10-16(30-3)12-17(11-14)31-4/h5,10-12,15,24H,1,8-9,13H2,2-4H3,(H2,23,29)/t15-/m0/s1
comment: The chemical structure for gunagratinib was obtained from WHO Proposed list 125. It mapped to PubChem CID 138734912, and from a web search it was identified as ICP-192, which is an irreversible pan-FGFR (fibroblast growth factor receptors) inhibitor that was developed by InnoCare Pharma for antitumuor potential (especially for tumours with FGF/FGFR gene aberrations). When we generated this ligand entry in August 2021, there was no published/peer reviewed report of ICP-192's pharmacology or biological activity. Phase 1 results were reported in a meeting abstract from the 2021 annual meeting of the American Society of Clinical Oncology DOI: 10.1200/JCO.2021.39.15_suppl.4092.
iupac name: 3-[2-(3,5-dimethoxyphenyl)ethynyl]-5-(methylamino)-1-[(3S)-1-prop-2-enoylpyrrolidin-3-yl]pyrazole-4-carboxamide
synonym: ICP-192
synonym: ICP192
approved: f
ligand name: gunagratinib
type: SyntheticOrganicLigand

gemnelatinib
isomeric SMILES: [C@H](C)(n1cc(cc(C)c1=O)c1nccc(c1)C#N)c1cc(ccc1)c1ncccn1
in ch i key: XVQSNGJANOEGEE-QGZVFWFLSA-N
in ch i: InChI=1S/C24H19N5O/c1-16-11-21(22-12-18(14-25)7-10-26-22)15-29(24(16)30)17(2)19-5-3-6-20(13-19)23-27-8-4-9-28-23/h3-13,15,17H,1-2H3/t17-/m1/s1
comment: This chemical structure was obtained from WHO Proposed list 125. It is recorded as a tyrosine kinase inhibitor with potential antineoplastic activity. As of August 2021, it appears to be an undisclosed agent, with no definitive molecular target, no presence in online chemistry resources, and the term 'gemnelatinib' does not retrieve any hits from a web search.
approved: f
ligand name: gemnelatinib
type: SyntheticOrganicLigand

elunonavir
in ch i key: ZTSLYWLHCOINNI-FTEFBJIISA-N
comment: The chemical structure for elunonavir was obtained from WHO Proposed list 125. The IUPAC>SMILES conversion maps to PubChem CID 135301900. Via SureChEMBL we can trace this compound to a Gilead Sciences patent that claims antiviral compounds for the treatment of HIV <Reference id=42655/>. From the patent it would appear that elunonavir is an HIV protease inhibitor.
iupac name: methyl N-[(2S)-1-[2-[[4-[1-(difluoromethyl)pyrazol-3-yl]-2,6-difluorophenyl]methyl]-2-[(2S,3S)-2-hydroxy-4-[4-[2-[2-[8-(oxetan-3-yl)-3,8-diazabicyclo[3.2.1]octan-3-yl]pyrimidin-5-yl]ethynyl]phenyl]-3-[[(2S)-4,4,4-trifluoro-2-(methoxycarbonylamino)-3,3-dimethylbutanoyl]amino]butyl]hydrazinyl]-4,4,4-trifluoro-3,3-dimethyl-1-oxobutan-2-yl]carbamate
approved: f
ligand name: elunonavir
type: SyntheticOrganicLigand

atuzabrutinib
in ch i key: KZMQPYCXSAGLTB-ZWUNQBBJSA-N
in ch i: InChI=1S/C30H30FN7O2/c1-30(2,3)15-19(16-32)29(39)37-13-7-8-20(17-37)38-28-25(27(33)34-18-35-28)26(36-38)23-12-11-22(14-24(23)31)40-21-9-5-4-6-10-21/h4-6,9-12,14-15,18,20H,7-8,13,17H2,1-3H3,(H2,33,34,35)/b19-15+/t20-/m1/s1
comment: Atuzabrutinib is a Bruton's tyrosine kinase inhibitor. The chemical structure was obtained from WHO Proposed list 125. Atuzabrutinib's structure matches example 125A as claimed in Principia Biopharma's patent US9090621B2 <Reference id=42654/>.
iupac name: (E)-2-[(3R)-3-[4-amino-3-(2-fluoro-4-phenoxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]piperidine-1-carbonyl]-4,4-dimethylpent-2-enenitrile
xref: CHEMBL4114766
approved: f
ligand name: atuzabrutinib
type: SyntheticOrganicLigand

XMD-12
in ch i key: DFQAJLQXPSPNJE-UHFFFAOYSA-N
in ch i: InChI=1S/C24H26N6O2/c1-28-20-6-4-3-5-19(20)23(32)29(2)21-15-25-24(27-22(21)28)26-16-7-9-17(10-8-16)30-13-11-18(31)12-14-30/h3-10,15,18,31H,11-14H2,1-2H3,(H,25,26,27)
comment: XMD-12 is a pan-Aurora kinase inhibitor <Reference id=42642/>. It is active in cell assays, but activity in vivo has not been demonstrated. It should be used in conjunction with other Aurora kinase inhibitors (e.g. <Ligand id=5718/>, <Ligand id=5696/>) to validate on-target effects.
iupac name: 2-[4-(4-hydroxypiperidin-1-yl)anilino]-5,11-dimethylpyrimido[4,5-b][1,4]benzodiazepin-6-one
synonym: compound 1 [PMID: 21992004]
synonym: XMD12
approved: f
ligand name: XMD-12
type: SyntheticOrganicLigand

luvixasertib
in ch i key: PMQUGSPFUBGJCZ-UHFFFAOYSA-N
in ch i: InChI=1S/C28H30N6O3/c1-17-10-19(5-8-22(17)27(35)32-20-6-7-20)23-16-31-34-24(30-14-18-12-28(2,36)13-18)11-25(33-26(23)34)37-21-4-3-9-29-15-21/h3-5,8-11,15-16,18,20,30,36H,6-7,12-14H2,1-2H3,(H,32,35)
comment: CFI-402257 is an orally bioavailable, and somewhat selective type 1.5 inhibitor of threonine tyrosine kinase (TTK) <Reference id=42640/><Reference id=42641/>. TTK inhibitors are under investigation as anticancer agents. CFI-402257 induces chromosome missegregation and aneuploidy which lead to cell death. We matched CFI-402257's chemical structure to the INN 'luvixasertib' that was released in the WHO's proposed INN list 127 (21 July 2022).
iupac name: N-cyclopropyl-4-[7-[(3-hydroxy-3-methylcyclobutyl)methylamino]-5-pyridin-3-yloxypyrazolo[1,5-a]pyrimidin-3-yl]-2-methylbenzamide
synonym: CFI402257
synonym: compound 24 [PMID: 27437075]
synonym: CFI-402257
approved: f
ligand name: luvixasertib
type: SyntheticOrganicLigand

MLI-2
in ch i key: ATUUNJCZCOMUKD-OKILXGFUSA-N
in ch i: InChI=1S/C21H25N5O2/c1-13-10-26(11-14(2)27-13)19-9-18(22-12-23-19)20-16-8-15(28-21(3)6-7-21)4-5-17(16)24-25-20/h4-5,8-9,12-14H,6-7,10-11H2,1-3H3,(H,24,25)/t13-,14+
comment: MLI-2 is an orally available and selective leucine-rich repeat kinase 2 (LRRK2) inhibitor <Reference id=42637/>. Activating mutations in LRRK2 (e.g. G2019S) are associated with an increased risk for the development of Parkinson's disease. Selective, brain-penetrant LRRK2 inhibitors are of clinical interest as a novel approach to treat Parkinson's disease. MLI-2 reduces brain LRRK2 kinase activity in vivo (determined by measuring phosphoS935 LRRK2) <Reference id=42638/>.
xref: CHEMBL4098877
synonym: MLi-2
synonym: compound 1 [PMID: 28245354]
approved: f
ligand name: MLI-2
type: SyntheticOrganicLigand

CP-10
in ch i key: MZTSDEMVUMXQFP-UHFFFAOYSA-N
in ch i: InChI=1S/C43H47N13O7/c1-26-31-22-46-43(49-38(31)55(28-5-2-3-6-28)41(61)32(26)25-57)47-35-11-9-29(21-45-35)53-16-14-52(15-17-53)23-27-24-54(51-50-27)18-20-63-19-13-44-33-8-4-7-30-37(33)42(62)56(40(30)60)34-10-12-36(58)48-39(34)59/h4,7-9,11,21-22,24-25,28,34,44H,2-3,5-6,10,12-20,23H2,1H3,(H,48,58,59)(H,45,46,47,49)
comment: CP-10 is a selective CDK6 degrading PROTAC <Reference id=42636/>. It is a bifunctional molecule that combines the CDK4/6 inhibitor <Ligand id=7380/>, with the cereblon ligand <Ligand id=7348/>. The pomalidomide moiety recruits E3 ubiquitin ligase machinery to the palbociclib-bound kinase protein, which leads to proteasomal degradation of CDK6. Selectivity of CP-10 appears to be cell line dependent, so CDK4 levels should be monitored to detect off-target activity, given palbociclib's selectivity profile for CDK6 and CDK4. CP-10 degrades mutant forms of CDK6 (e.g. CDK6D163G) as efficiently as it degrades wild-type kinase protein, and it induces degradation of CDK6 and CDK4 and inhibits the proliferation in palbociclib resistant cell lines.
xref: CHEMBL4553408
approved: f
ligand name: CP-10
type: SyntheticOrganicLigand

daridorexant
in ch i key: NBGABHGMJVIVBW-QHCPKHFHSA-N
in ch i: InChI=1S/C23H23ClN6O2/c1-14-17(24)6-7-18-20(14)28-22(27-18)23(2)9-4-12-29(23)21(31)16-13-15(32-3)5-8-19(16)30-25-10-11-26-30/h5-8,10-11,13H,4,9,12H2,1-3H3,(H,27,28)/t23-/m0/s1
comment: Daridorexant (ACT-541468) is a dual orexin receptor antagonist <Reference id=42598/><Reference id=43287/>. It was designed and developed for potential to treat insomnia <Reference id=42596/><Reference id=42595/><Reference id=42597/><Reference id=42959/><Reference id=42960/>.
iupac name: [(2S)-2-(5-chloro-4-methyl-1H-benzimidazol-2-yl)-2-methylpyrrolidin-1-yl]-[5-methoxy-2-(triazol-2-yl)phenyl]methanone
xref: CHEMBL4297590
synonym: ACT-541468
synonym: ACT541468
synonym: nemorexant (former name)
synonym: Quviviq®
approved: t
ligand name: daridorexant
type: SyntheticOrganicLigand

TBK1 PROTAC 3i
in ch i key: QMGHHBHPDDAGGO-IIWOMYBWSA-N
comment: This compound (3i) is a TANK-binding kinase 1 (TBK1) PROTAC degrader <Reference id=42635/>. The TBK1 inhibitor portion of the molecule binds the kinase and the Von Hippel-Lindau (VHL) binding portion of the molecule recruits an E3 ubiquitin ligase to the bound kinase and this leads to proteasomal degradation of the kinase protein. This PROTAC was used to evaluate TBK1 as a target in mutant KRAS cancer cells. 3i does not promote degradation of closely related IKKε which has 65% sequence homology with TBK1.
xref: CHEMBL4227907
synonym: compound 3i [PMID: 28692295]
approved: f
ligand name: TBK1 PROTAC 3i
type: SyntheticOrganicLigand

2-methylhistamine
canonical SMILES: OCCN1CN(CO)C(=S)N(C1)CO
isomeric SMILES: OCCN1CN(CO)C(=S)N(C1)CO
in ch i key: ZGUKXHGPXOTTSU-UHFFFAOYSA-N
in ch i: InChI=1S/C7H15N3O3S/c11-2-1-8-3-9(5-12)7(14)10(4-8)6-13/h11-13H,1-6H2
iupac name: 5-(2-hydroxyethyl)-1,3-bis(hydroxymethyl)-1,3,5-triazinane-2-thione
approved: f
ligand name: 2-methylhistamine
type: SyntheticOrganicLigand

foslinanib
in ch i key: ZDWFMAHQGDEALT-UHFFFAOYSA-N
in ch i: InChI=1S/C16H13FNO6P/c1-23-14-6-5-11-15(16(14)24-25(20,21)22)13(19)8-12(18-11)9-3-2-4-10(17)7-9/h2-8H,1H3,(H,18,19)(H2,20,21,22)
comment: Foslinanib (CVM-1118) is an orally bioavailable protein kinase inhibitor with antiangiogenic and antineoplastic activities <Reference id=42529/>.
iupac name: [2-(3-fluorophenyl)-6-methoxy-4-oxo-1H-quinolin-5-yl] dihydrogen phosphate
synonym: CVM-1118
synonym: TRX-818
synonym: TRX 818
approved: f
ligand name: foslinanib
type: SyntheticOrganicLigand

compound 38k [PMID: 34351741]
in ch i key: ZYZUOYYVHYGMDE-UHFFFAOYSA-N
comment: Compound 38k is a potent inhibitor of vascular endothelial growth factor receptor 3 (VEGFR3) <Reference id=42632/>. It is proposed as a novel therapeutic agent for the treatment of metastatic breast cancer. Compound 38k suppresses the VEGFR3 signalling pathway, bringing about apoptosis in target cells.
iupac name: N-(4-Chloro-3-(trifluoromethyl)phenyl)-4-(6-(4-(4-methylpiperazin-1-yl)phenyl)thieno[2,3-d]pyrimidin-4-yl)piperazine-1-carboxamide
approved: f
ligand name: compound 38k [PMID: 34351741]
type: SyntheticOrganicLigand

CC-90005
in ch i key: FMKGJQHNYMWDFJ-CVEARBPZSA-N
in ch i: InChI=1S/C21H27F2N7O2/c1-20(2)6-15(4-5-16(20)31)29-17-13(7-24)9-26-19(30-17)27-10-14-8-25-12-28-18(14)32-11-21(3,22)23/h8-9,12,15-16,31H,4-6,10-11H2,1-3H3,(H2,26,27,29,30)/t15-,16+/m1/s1
comment: CC-90005 is reported as a selective protein kinase C theta (PCKθ) inhibitor <Reference id=42628/>. It was developed by Celgene for potential to inhibit TCR-mediated T cell activation, proliferation, and cytokine production, as an anti-inflammatory modality for the treatment of T cell-driven autoimmune diseases <Reference id=42629/>. CC-90005 induces T cell anergy. It is >550-fold selective for PCKθ compared to PCKδ.
iupac name: 2-[[4-(2,2-difluoropropoxy)pyrimidin-5-yl]methylamino]-4-[[(1R,4S)-4-hydroxy-3,3-dimethylcyclohexyl]amino]pyrimidine-5-carbonitrile
synonym: compound 57 [PMID: 34355886]
approved: f
ligand name: CC-90005
type: SyntheticOrganicLigand

CCF981
in ch i key: NQTRFDLUODRJKC-UHFFFAOYSA-N
in ch i: InChI=1S/C24H19ClN6O/c25-19-5-3-4-17(12-19)14-30(20-10-8-18(9-11-20)22-13-26-16-27-22)24(32)15-31-23-7-2-1-6-21(23)28-29-31/h1-13,16H,14-15H2,(H,26,27)
comment: CCF981 is a potent noncovalent inhibitor of the 3CL proteinase (Mpro) of SARS-CoV-2 <Reference id=42620/>. It was designed on the scaffold of <Ligand id=11657/> using structure-based optimization. Unsurprisingly CCF981 also inhibits SARS-CoV Mpro.
iupac name: N-[4-(1H-Imidazol-4-yl)phenyl]-2-(1H-benzo[d][1,2,3]triazol-1-yl)-N-(3-chlorobenzyl)acetamide
synonym: compound 41 [PMID: 34347470]
synonym: CCF0058981
approved: f
ligand name: CCF981
type: SyntheticOrganicLigand

ML300
in ch i key: OCKMJWOFMCSMEX-UHFFFAOYSA-N
in ch i: InChI=1S/C23H21N5O2S/c29-22(14-28-21-4-2-1-3-20(21)25-26-28)27(13-16-11-12-31-15-16)19-9-7-18(8-10-19)24-23(30)17-5-6-17/h1-4,7-12,15,17H,5-6,13-14H2,(H,24,30)
comment: ML300 was originally designed as a noncovalent, non-peptide-like inhibitor of SARS-CoV 3CL proteinase (Mpro) <Reference id=42618/>. It also inhibits Mpro of SARS-CoV-2 <Reference id=42620/>.
xref: CHEMBL2442081
synonym: compound 16e [PMID: 24080461]
synonym: ML-300
approved: f
ligand name: ML300
type: SyntheticOrganicLigand

kelatorphan
in ch i key: OJCFZTVYDSKXNM-GXSJLCMTSA-N
in ch i: InChI=1S/C14H18N2O5/c1-9(14(19)20)15-13(18)11(8-12(17)16-21)7-10-5-3-2-4-6-10/h2-6,9,11,21H,7-8H2,1H3,(H,15,18)(H,16,17)(H,19,20)/t9-,11+/m0/s1
comment: Kelatorphan is an inhibitor of zinc metallopeptidases. The structure of kelatorphan bound to leukotriene A4 hydrolase has been determined by X-ray crystallography <Reference id=42612/>
xref: CHEMBL85320
approved: f
ligand name: kelatorphan
type: SyntheticOrganicLigand

phelorphan
in ch i key: DPRJEBOTAKMRQV-IRXDYDNUSA-N
in ch i: InChI=1S/C20H22N2O4S/c23-18(13-27)21-16(11-14-7-3-1-4-8-14)19(24)22-17(20(25)26)12-15-9-5-2-6-10-15/h1-10,16-17,27H,11-13H2,(H,21,23)(H,22,24)(H,25,26)/t16-,17-/m0/s1
comment: Phelorphan is an inhibitor of enkephalin-degrading enzymes <Reference id=42611/>.
synonym: deamino-norcysteinyl-L-phenylalanyl-L-phenylalanine
approved: f
ligand name: phelorphan
type: PeptideLigand

racecadotril
in ch i key: ODUOJXZPIYUATO-UHFFFAOYSA-N
in ch i: InChI=1S/C21H23NO4S/c1-16(23)27-15-19(12-17-8-4-2-5-9-17)21(25)22-13-20(24)26-14-18-10-6-3-7-11-18/h2-11,19H,12-15H2,1H3,(H,22,25)
comment: Racecadotril (acetorphan) is an orally administered antidiarrheal drug. It is a prodrug that is hydrolysed to its active metabolite thiorphan (an enkephalinase inhibitor).
iupac name: benzyl 2-[[2-(acetylsulfanylmethyl)-3-phenylpropanoyl]amino]acetate
synonym: acetorphan
synonym: Hidrasec®
synonym: (+/-)-acetorphan
approved: t
ligand name: racecadotril
type: SyntheticOrganicLigand

phosphoramidon
in ch i key: ZPHBZEQOLSRPAK-XLCYBJAPSA-N
in ch i: InChI=1S/C23H34N3O10P/c1-11(2)8-16(26-37(33,34)36-23-20(29)19(28)18(27)12(3)35-23)21(30)25-17(22(31)32)9-13-10-24-15-7-5-4-6-14(13)15/h4-7,10-12,16-20,23-24,27-29H,8-9H2,1-3H3,(H,25,30)(H,31,32)(H2,26,33,34)/t12-,16-,17-,18-,19+,20+,23-/m0/s1
comment: Phosphoramidon is used as a biochemical tool for its inhibitory activity against metallo-endopeptidases, including neutral endopeptidase, endothelin-converting enzymes and angiotensin-converting enzyme <Reference id=42609/>.
xref: CHEMBL479579
approved: f
ligand name: phosphoramidon
type: SyntheticOrganicLigand

RB3007
in ch i key: PYJMLILRVYLUHW-UNCDKACKSA-N
in ch i: InChI=1S/C37H41N2O6PS/c1-27(37(42)44-25-30-12-6-3-7-13-30)39-36(41)34(24-29-18-20-32(21-19-29)31-14-8-4-9-15-31)26-46(43,45-22-23-47-28(2)40)35(38)33-16-10-5-11-17-33/h3-21,27,34-35H,22-26,38H2,1-2H3,(H,39,41)/t27-,34+,35+,46?/m0/s1
comment: RB3007 is a systemically delivered, dual inhibitor of the enkephalin-degrading enzymes neutral endopeptidase/aminopeptidase N <Reference id=42608/>. It can be used as an in vivo biological tool. Aminopeptidase N/neprilysin inhibition with RB3007 induces an elevation in the levels of the two endogenous enkephalins <Ligand id=1614/> and <Ligand id=1613/>, Prodrugs with this mechanism of action are known collectively as Dual Enkephalinase Inhibitors, or DENKIs.
synonym: RB-3007
synonym: RB 3007
approved: f
ligand name: RB3007
type: SyntheticOrganicLigand

RB120
in ch i key: XHWYFTNNIZGHRW-PMOQBDJRSA-N
in ch i: InChI=1S/C25H34N2O3S3/c1-19(25(29)30-16-21-11-7-4-8-12-21)27-24(28)22(15-20-9-5-3-6-10-20)17-32-33-18-23(26)13-14-31-2/h3-12,19,22-23H,13-18,26H2,1-2H3,(H,27,28)/t19-,22+,23-/m0/s1
comment: RB120 is an orally active, dual inhibitor of the enkephalin-degrading enzymes neutral endopeptidase/aminopeptidase N <Reference id=42607/>. It is an analogue of <Ligand. id=11650/>, and is used as a biological tool. Prodrugs with this mechanism of action are known collectively as Dual Enkephalinase Inhibitors, or DENKIs.
iupac name: benzyl (2S)-2-[[(2S)-2-[[[(2S)-2-amino-4-methylsulfanylbutyl]disulfanyl]methyl]-3-phenylpropanoyl]amino]propanoate
xref: CHEMBL3299158
synonym: RB 120
synonym: RB-120
approved: f
ligand name: RB120
type: SyntheticOrganicLigand

RB101
in ch i key: QXXMSEVVNUSHKJ-PPUMFKDSSA-N
in ch i: InChI=1S/C31H38N2O3S3/c1-37-18-17-28(32)23-39-38-22-27(19-24-11-5-2-6-12-24)30(34)33-29(20-25-13-7-3-8-14-25)31(35)36-21-26-15-9-4-10-16-26/h2-16,27-29H,17-23,32H2,1H3,(H,33,34)/t27?,28?,29-/m0/s1
comment: RB101 is an enkephalinase inhibitor, that is used as a biological tool <Reference id=42605/>. It is metabolically cleaved into two active components, each of which inhibits one of the zinc-metallopeptidase enkephalin-degrading enzymes, aminopeptidase N (APN; ANPEP) and neutral endopeptidase (neprilysin; official gene name membrane metalloendopeptidase MME) <Reference id=42606/>. Aminopeptidase N/neprilysin inhibition with RB101 induces an elevation in the levels of the two endogenous enkephalins <Ligand id=1614/> and <Ligand id=1613/>. Prodrugs with this mechanism of action are known collectively as Dual Enkephalinase Inhibitors, or DENKIs.
iupac name: benzyl (2S)-2-[[2-[[(2-amino-4-methylsulfanylbutyl)disulfanyl]methyl]-3-phenylpropanoyl]amino]-3-phenylpropanoate
synonym: RB 101
synonym: RB-101
approved: f
ligand name: RB101
type: SyntheticOrganicLigand

Honokiol
canonical SMILES: C=CCc1ccc(c(c1)c1ccc(c(c1)CC=C)O)O
isomeric SMILES: C=CCc1ccc(c(c1)c1ccc(c(c1)CC=C)O)O
in ch i key: FVYXIJYOAGAUQK-UHFFFAOYSA-N
in ch i: InChI=1S/C18H18O2/c1-3-5-13-7-9-18(20)16(11-13)14-8-10-17(19)15(12-14)6-4-2/h3-4,7-12,19-20H,1-2,5-6H2
comment: Honokiol is a lignan that is produced by Magnolia trees that has been widely used in traditional medicine in East Asia. It has been described as having many pharmacological effects <Reference id=42483/><Reference id=42484/><Reference id=42485/><Reference id=42487/>, with activities at a number of protein targets <Reference id=42486/>. Honokiol's anti-cancer potential has been extensively investigated <Reference id=42484/>.
iupac name: 2-(4-hydroxy-3-prop-2-enylphenyl)-4-prop-2-enylphenol
xref: CHEMBL16901
approved: f
ligand name: Honokiol
type: NaturalProductLigand

gartisertib
in ch i key: QAYHKBLKSXWOEO-UHFFFAOYSA-N
in ch i: InChI=1S/C25H29F2N9O3/c26-16-9-30-23-20(22(28)32-36(23)12-16)24(37)31-19-11-29-10-18(27)21(19)34-3-1-15(2-4-34)25(38)35-7-5-33(6-8-35)17-13-39-14-17/h9-12,15,17H,1-8,13-14H2,(H2,28,32)(H,31,37)
comment: M4344 (VX-803) is a small molecule, ATP-competitive, selective and orally deliverable inhibitor of the DNA damage response pathway kinase, ataxia telangiectasia and rad3-related (ATR) <Reference id=42584/>. The chemical structure of M4344 matches that for gartisertib, which was surfaced in WHO Proposed list 125 in July 2021.
iupac name: 2-amino-6-fluoro-N-[5-fluoro-4-[4-[4-(oxetan-3-yl)piperazine-1-carbonyl]piperidin-1-yl]pyridin-3-yl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Computed by Lexi
synonym: VX-803
synonym: VX803
synonym: M-4344
synonym: M4344
approved: f
ligand name: gartisertib
type: SyntheticOrganicLigand

gumarontinib
in ch i key: RYBLECYFLJXEJX-UHFFFAOYSA-N
in ch i: InChI=1S/C21H17N9O2S/c1-27-11-16(7-24-27)14-3-4-20-23-10-21(29(20)13-14)33(31,32)30-19-5-15(6-22-18(19)9-26-30)17-8-25-28(2)12-17/h3-13H,1-2H3
comment: Gumarontinib (SCC224) is an oral potent and highly selective c-MET inhibitor <Reference id=42534/>. It was developed for potential to treat MET-dependent tumours.
iupac name: 6-(1-methylpyrazol-4-yl)-1-[6-(1-methylpyrazol-4-yl)imidazo[1,2-a]pyridin-3-yl]sulfonylpyrazolo[4,3-b]pyridine
xref: CHEMBL4594400
synonym: SCC224
synonym: SCC-224
synonym: glumetinib (pseoudo INN)
approved: f
ligand name: gumarontinib
type: SyntheticOrganicLigand

YH-53
in ch i key: JBLLRCOZJMVOAE-HSQYWUDLSA-N
in ch i: InChI=1S/C30H33N5O5S/c1-16(2)13-22(34-29(39)23-15-18-19(32-23)8-6-9-24(18)40-3)28(38)33-21(14-17-11-12-31-27(17)37)26(36)30-35-20-7-4-5-10-25(20)41-30/h4-10,15-17,21-22,32H,11-14H2,1-3H3,(H,31,37)(H,33,38)(H,34,39)/t17-,21-,22-/m0/s1
comment: YH-53 is a peptidomimetic, covalent inhibitor of coronavirus 3CL protease (3CLpro, Mpro), with reported inhibition of Mpro from SARS-CoV and SARS-CoV-2 <Reference id=42570/><Reference id=42572/><Reference id=42571/>.
synonym: YH53
synonym: compound 5h [PMID: 33510133]
synonym: compound 5h [PMID: 23994330]
synonym: GRL-2420 (compound 3 PMID: 34528437)
approved: f
ligand name: YH-53
type: SyntheticOrganicLigand

calpeptin
in ch i key: PGGUOGKHUUUWAF-ROUUACIJSA-N
in ch i: InChI=1S/C20H30N2O4/c1-4-5-11-17(13-23)21-19(24)18(12-15(2)3)22-20(25)26-14-16-9-7-6-8-10-16/h6-10,13,15,17-18H,4-5,11-12,14H2,1-3H3,(H,21,24)(H,22,25)/t17-,18-/m0/s1
comment: Calpeptin is a dipeptidyl inhibitor of calpain cysteine proteases.
iupac name: benzyl N-[(2S)-4-methyl-1-oxo-1-[[(2S)-1-oxohexan-2-yl]amino]pentan-2-yl]carbamate
xref: CHEMBL92708
synonym: N-benzyloxycarbonyl-L-leucyl-L-norleucinal
synonym: benzylcarbonyl-Leu-nLeu-H
approved: f
ligand name: calpeptin
type: PeptideLigand

compound 25c [PMID: 23747811]
in ch i key: AJRQIXBBIDPNGK-BVSLBCMMSA-N
in ch i: InChI=1S/C28H32N4O5S/c1-17(2)14-22(32-28(36)37-16-18-8-4-3-5-9-18)26(35)30-21(15-19-12-13-29-25(19)34)24(33)27-31-20-10-6-7-11-23(20)38-27/h3-11,17,19,21-22H,12-16H2,1-2H3,(H,29,34)(H,30,35)(H,32,36)/t19-,21-,22-/m0/s1
comment: Compound 25c was originally reported as an inhibitor of SARS-CoV 3CL protease (Mpro) <Reference id=42561/>. It is virtually inactive against SARS-CoV-2 Mpro (IC50 >10 μM) <Reference id=42556/>.
iupac name: benzyl N-[(2S)-1-[[(2S)-1-(1,3-benzothiazol-2-yl)-1-oxo-3-[(3S)-2-oxopyrrolidin-3-yl]propan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]carbamate
xref: CHEMBL2402501
approved: f
ligand name: compound 25c [PMID: 23747811]
type: PeptideLigand

compound 3 [PMID: 16884309]
in ch i key: WDMSWWUPIMEGNZ-UHFFFAOYSA-N
in ch i: InChI=1S/C30H44N4O7/c1-6-40-25(35)13-12-23(17-22-14-15-31-27(22)36)32-28(37)24(16-19(2)3)33-29(38)26(20(4)5)34-30(39)41-18-21-10-8-7-9-11-21/h7-13,19-20,22-24,26H,6,14-18H2,1-5H3,(H,31,36)(H,32,37)(H,33,38)(H,34,39)
comment: Compound 3 is an analogue of the SARS coronavirus (CoV) 3CL protease inhibitor <Ligand id=11176/> <Reference id=40146/>.
iupac name: ethyl 4-[[4-methyl-2-[[3-methyl-2-(phenylmethoxycarbonylamino)butanoyl]amino]pentanoyl]amino]-5-(2-oxopyrrolidin-3-yl)pent-2-enoate
approved: f
ligand name: compound 3 [PMID: 16884309]
type: PeptideLigand

MG-115
in ch i key: QEJRGURBLQWEOU-FKBYEOEOSA-N
in ch i: InChI=1S/C25H39N3O5/c1-6-10-20(15-29)26-23(30)21(13-17(2)3)27-24(31)22(14-18(4)5)28-25(32)33-16-19-11-8-7-9-12-19/h7-9,11-12,15,17-18,20-22H,6,10,13-14,16H2,1-5H3,(H,26,30)(H,27,31)(H,28,32)/t20-,21-,22-/m0/s1
comment: MG-115 was first reported as an irreversible proteasome inhibitor <Reference id=42560/>.
iupac name: benzyl N-[(2S)-4-methyl-1-[[(2S)-4-methyl-1-oxo-1-[[(2S)-1-oxopentan-2-yl]amino]pentan-2-yl]amino]-1-oxopentan-2-yl]carbamate
xref: CHEMBL4518490
synonym: Cbz-Leu-Leu-norvalinal
synonym: N-benzyloxycarbonyl-L-leucyl-L-leucyl-L-norvalinal
synonym: Z-LL-Nva-CHO
approved: f
ligand name: MG-115
type: PeptideLigand

GC-373
in ch i key: QYENXTYKACLCGO-FQECFTEESA-N
in ch i: InChI=1S/C21H29N3O5/c1-14(2)10-18(24-21(28)29-13-15-6-4-3-5-7-15)20(27)23-17(12-25)11-16-8-9-22-19(16)26/h3-7,12,14,16-18H,8-11,13H2,1-2H3,(H,22,26)(H,23,27)(H,24,28)/t16?,17-,18-/m0/s1
comment: GC-373 is the parent of the dipeptide-based prodrug <Ligand id=10883/>. The aldehyde drug and bisulphite adduct prodrug were originally reported as inhibitors of the 3CL protease (Mpro) of feline coronaviruses and caliciviruses <Reference id=42558/>. They also inhibit Mpro of both SARS-CoV and SARS-CoV-2, and inhibit SARS-CoV-2 replication in cell culture <Reference id=42557/>.
xref: CHEMBL1821850
synonym: GC373
synonym: N-benzyloxycarbonyl-L-leucyl-3-(2-oxopyrrolidin-3-yl)-L-alaninal
approved: f
ligand name: GC-373
type: PeptideLigand

compound 2i [PMID: 23245752]
in ch i key: KSCRVOKQPYZBHZ-IXPOFIJOSA-N
in ch i: InChI=1S/C33H41N5O6S/c1-19(2)16-25(36-31(42)27(20(3)4)38-33(43)44-18-21-10-6-5-7-11-21)30(41)35-24(17-22-14-15-34-29(22)40)28(39)32-37-23-12-8-9-13-26(23)45-32/h5-13,19-20,22,24-25,27H,14-18H2,1-4H3,(H,34,40)(H,35,41)(H,36,42)(H,38,43)/t22-,24-,25-,27-/m0/s1
comment: Compound 2i was originally reported as a tripeptide-type SARS-CoV 3CL protease inhibitor <Reference id=42555/>. It has subsequently been shown to inhibit SARS-CoV-2 3CL protease <Reference id=42556/>.
xref: CHEMBL2316746
approved: f
ligand name: compound 2i [PMID: 23245752]
type: SyntheticOrganicLigand

famciclovir
canonical SMILES: CC(=O)OCC(CCn1cnc2c1nc(N)nc2)COC(=O)C
isomeric SMILES: CC(=O)OCC(CCn1cnc2c1nc(N)nc2)COC(=O)C
in ch i key: GGXKWVWZWMLJEH-UHFFFAOYSA-N
in ch i: InChI=1S/C14H19N5O4/c1-9(20)22-6-11(7-23-10(2)21)3-4-19-8-17-12-5-16-14(15)18-13(12)19/h5,8,11H,3-4,6-7H2,1-2H3,(H2,15,16,18)
comment: Famciclovir is an orally-delivered, prodrug of the antiviral agent penciclovir <Reference id=42543/>. The active metabolite, penciclovir triphosphate, has activity against Herpes viruses and varicella-zoster. Penciclovir triphosphate is a nucleoside analogue that inhibits viral DNA replication by interfering competitively with DNA polymerase.
iupac name: [2-(acetyloxymethyl)-4-(2-aminopurin-9-yl)butyl] acetate
xref: CHEMBL880
synonym: Famvir®
synonym: BRL-42810
synonym: BRL42810
synonym: FCV
approved: t
ligand name: famciclovir
type: SyntheticOrganicLigand

pirtobrutinib
in ch i key: FWZAWAUZXYCBKZ-NSHDSACASA-N
in ch i: InChI=1S/C22H21F4N5O3/c1-11(22(24,25)26)31-19(27)17(20(28)32)18(30-31)13-5-3-12(4-6-13)10-29-21(33)15-9-14(23)7-8-16(15)34-2/h3-9,11H,10,27H2,1-2H3,(H2,28,32)(H,29,33)/t11-/m0/s1
comment: Pirtobrutinib (LOXO-305) is a clinical stage, selective and reversible, oral Bruton' tyrosine kinase (BTK) inhibitor that was developed by LOXO oncology <Reference id=42540/><Reference id=42542/>.
iupac name: 5-amino-3-[4-[[(5-fluoro-2-methoxybenzoyl)amino]methyl]phenyl]-1-[(2S)-1,1,1-trifluoropropan-2-yl]pyrazole-4-carboxamide
synonym: LOXO-305
synonym: LOXO305
synonym: BTK inhibitor 16
approved: f
ligand name: pirtobrutinib
type: SyntheticOrganicLigand

piclamilast
in ch i key: RRRUXBQSQLKHEL-UHFFFAOYSA-N
comment: Piclamilast (RP-73401) is a potent and selective inhibitor of phosphodiesterase 4 (PDE4) <Reference id=42538/>.
iupac name: 3-cyclopentyloxy-N-(3,5-dichloropyridin-4-yl)-4-methoxybenzamide
xref: CHEMBL42126
synonym: RP 73401
synonym: RP73401
synonym: RP-73-401
approved: f
ligand name: piclamilast
type: SyntheticOrganicLigand

PF-05180999
in ch i key: CLGCHUKGBICQTE-UHFFFAOYSA-N
in ch i: InChI=1S/C19H17F3N8/c1-11-27-15(17-18(29-6-3-7-29)24-10-26-30(11)17)13-9-25-28(2)16(13)14-5-4-12(8-23-14)19(20,21)22/h4-5,8-10H,3,6-7H2,1-2H3
comment: PF-05180999 is a selective and brain-penetrant inhibitor of phosphodiesterase 2A (PDE2A) <Reference id=42537/><Reference id=42546/>. Its intended clinical utility was to target cognitive impairment associated with schizophrenia.
iupac name: 4-(azetidin-1-yl)-7-methyl-5-[1-methyl-5-[5-(trifluoromethyl)pyridin-2-yl]pyrazol-4-yl]imidazo[5,1-f][1,2,4]triazine
xref: CHEMBL3092562
synonym: PF 05180999
synonym: PF05180999
synonym: PF-999
synonym: compound 30 [PMID: 29293004]
approved: f
ligand name: PF-05180999
type: SyntheticOrganicLigand

TC-E 5005
canonical SMILES: CCCc1nc(c2n1c1nc(OC)ccc1nc2C)C
isomeric SMILES: CCCc1nc(c2n1c1nc(OC)ccc1nc2C)C
in ch i key: YNADXFWEXJTQSZ-UHFFFAOYSA-N
in ch i: InChI=1S/C15H18N4O/c1-5-6-12-17-10(3)14-9(2)16-11-7-8-13(20-4)18-15(11)19(12)14/h7-8H,5-6H2,1-4H3
comment: TC-E 5005 is a potent and selective inhibitor of phosphodiesterase 10A (PDE10A) <Reference id=42536/><Reference id=42544/>.
xref: CHEMBL1086110
synonym: compound 1 [PMID: 21988093]
approved: f
ligand name: TC-E 5005
type: SyntheticOrganicLigand

BTT-3033
in ch i key: NSLIQOPYDUKWTA-UHFFFAOYSA-N
in ch i: InChI=1S/C23H20FN5O3S/c1-28(33(31,32)22-15-25-29(16-22)21-11-7-17(24)8-12-21)20-13-9-19(10-14-20)27-23(30)26-18-5-3-2-4-6-18/h2-16H,1H3,(H2,26,27,30)
comment: BTT-3033 is an α2β1 integrin inhibitor that blocks platelet attachment to collagen <Reference id=41849/>.
iupac name: 1-[4-[[1-(4-fluorophenyl)pyrazol-4-yl]sulfonyl-methylamino]phenyl]-3-phenylurea
xref: CHEMBL4303254
synonym: BTT 3033
synonym: BTT3033
approved: f
ligand name: BTT-3033
type: SyntheticOrganicLigand

ningetinib
in ch i key: VQYYQSZNRVQLIS-UHFFFAOYSA-N
in ch i: InChI=1S/C31H29FN4O5/c1-19-28(30(38)36(35(19)4)21-8-6-5-7-9-21)29(37)34-20-10-13-27(24(32)16-20)41-26-14-15-33-25-17-22(11-12-23(25)26)40-18-31(2,3)39/h5-17,39H,18H2,1-4H3,(H,34,37)
comment: Ningetinib (CT053) is an oral small molecule multiple tyrosine kinase inhibitor. It inhibits c-Met, VEGFR2, Axl, Mer, RON and FLT3.
xref: CHEMBL3984441
synonym: Example 1 [US9133162]
synonym: CT053PTSA
synonym: CT053
synonym: CT-053
approved: f
ligand name: ningetinib
type: SyntheticOrganicLigand

recilisib
canonical SMILES: Clc1ccc(cc1)CS(=O)(=O)/C=C/c1ccc(cc1)C(=O)O
isomeric SMILES: Clc1ccc(cc1)CS(=O)(=O)/C=C/c1ccc(cc1)C(=O)O
in ch i key: KBEKQQJUNVQLDZ-MDZDMXLPSA-N
in ch i: InChI=1S/C16H13ClO4S/c17-15-7-3-13(4-8-15)11-22(20,21)10-9-12-1-5-14(6-2-12)16(18)19/h1-10H,11H2,(H,18,19)/b10-9+
comment: Recilisib is a small molecule protein kinase inhibitor that modulates MAPK signalling via up-regulation of the PI3-kinase/AKT pathways <Reference id=42527/>. It was developed by Onconova Therapeutics for radioprotective action <Reference id=42527/>. Used experimentally as the sodium salt.
iupac name: 4-[(E)-2-[(4-chlorophenyl)methylsulfonyl]ethenyl]benzoic acid
xref: CHEMBL2219421
synonym: ON 01210
synonym: ON-01210
synonym: EX-RAD®
approved: f
ligand name: recilisib
type: SyntheticOrganicLigand

toceranib
canonical SMILES: Fc1ccc2c(c1)/C(=C/c1[nH]c(c(c1C)C(=O)NCCN1CCCC1)C)/C(=O)N2
isomeric SMILES: Fc1ccc2c(c1)/C(=C/c1[nH]c(c(c1C)C(=O)NCCN1CCCC1)C)/C(=O)N2
in ch i key: SRSGVKWWVXWSJT-ATVHPVEESA-N
in ch i: InChI=1S/C22H25FN4O2/c1-13-19(12-17-16-11-15(23)5-6-18(16)26-21(17)28)25-14(2)20(13)22(29)24-7-10-27-8-3-4-9-27/h5-6,11-12,25H,3-4,7-10H2,1-2H3,(H,24,29)(H,26,28)/b17-12-
comment: Toceranib (PHA-291639 and formerly SU11654) is a small molecule, multi-targeted receptor tyrosine kinase inhibitor <Reference id=23040/>. It is structurally related to <Ligand id=5713/>. Targets include VEGFRs, FGFR, PDGFRs, and Kit (including constitutively active mutant forms <Reference id=42526/>). Like sunitinib, toceranib has antiangiogenic and anitproliferative actions. Palladiar® branded toceranib is used to treat solid tumours in dogs.
xref: CHEMBL13608
synonym: PHA-291639
synonym: PHA291639
synonym: SU 11654
synonym: SU11654
synonym: SU-11654
synonym: Palladiar®
synonym: compound 12f [PMID: 12646019]
approved: f
ligand name: toceranib
type: SyntheticOrganicLigand

vorolanib
in ch i key: KMIOJWCYOHBUJS-HAKPAVFJSA-N
in ch i: InChI=1S/C23H26FN5O3/c1-12-19(10-17-16-9-14(24)5-6-18(16)27-21(17)30)25-13(2)20(12)22(31)26-15-7-8-29(11-15)23(32)28(3)4/h5-6,9-10,15,25H,7-8,11H2,1-4H3,(H,26,31)(H,27,30)/b17-10-/t15-/m0/s1
comment: Vorolanib (CM082) is a potent and selective, oral clinical stage multi-kinase inhibitor. Targets include all VEGFR isoforms, PDGFR and CSF1R. <Reference id=42521/><Reference id=42524/><Reference id=42525/>. It is a structural derivative of <Ligand id=5713/>. Vorolanib has anti-angiogenic activity, and is being investigated for anti-tumour effects and utility to treat ocular neovascularisation.
iupac name: N-[(3S)-1-(dimethylcarbamoyl)pyrrolidin-3-yl]-5-[(Z)-(5-fluoro-2-oxo-1H-indol-3-ylidene)methyl]-2,4-dimethyl-1H-pyrrole-3-carboxamide
xref: CHEMBL4297587
synonym: CM082
synonym: CM-082
synonym: X-82
synonym: Example 8 [WO2008033562A2]
synonym: EYP-1901
approved: f
ligand name: vorolanib
type: SyntheticOrganicLigand

GLPG4716
in ch i key: STWVLEKJQQRGMO-GUYCJALGSA-N
in ch i: InChI=1S/C19H27ClN6O/c1-13-11-26(17(12-27-13)10-14-2-4-15(20)5-3-14)16-6-8-25(9-7-16)19-22-18(21)23-24-19/h2-5,13,16-17H,6-12H2,1H3,(H3,21,22,23,24)/t13-,17-/m0/s1
comment: GLPG4716 (formerly OATD-01) is a first-in-class, orally bioavailable inhibitor of the chitinase enzymes chitinase 1 (chitotriosidase; CHIT1) and AMCase (chitinase acidic; CHIA) <Reference id=42510/>. Galapagos have in-licensed the rights to develop this compound from OncoArendi/Molecure. GLPG4716 was developed as a treatment for respiratory diseases, having demonstrated efficacy in in vivo models of asthma and pulmonary fibrosis, and sarcoidosis. In mid-2022 the Galapagos/Molecure partnership was terminated and all rights for OATD-01 were returned to Molecure.
iupac name: 3-[4-[(2S,5S)-5-[(4-chlorophenyl)methyl]-2-methylmorpholin-4-yl]piperidin-1-yl]-1H-1,2,4-triazol-5-amine
synonym: compound 9 [PMID: 33078933]
approved: f
ligand name: GLPG4716
type: SyntheticOrganicLigand

compound 21 [Zhang et al., 2021]
in ch i key: CMYSAEAJENJTSK-UHFFFAOYSA-N
comment: Compound 21 is one of two potential lead SARS-CoV-2 antivirals from the same discovery effort <Reference id=42508/>. Both compounds inhibit SARS-CoV-2 3CL protease (Mpro). <Ligand id=11615/> is the other lead.
iupac name: 5-[3-(3-chloro-5-{[4-(trifluoromethyl)-1,3-thiazol-5-yl]methoxy}phenyl)-2-oxo-2H-[1,3'-bipyridin]-5-yl]-1-methyl-1,2,3,4-tetrahydropyrimidine-2,4-dione
approved: f
ligand name: compound 21 [Zhang et al., 2021]
type: SyntheticOrganicLigand

compound 19 [Zhang et al., 2021]
in ch i key: KIJKUSPNZALBLD-UHFFFAOYSA-N
comment: Compound 19 is one of two potential lead SARS-CoV-2 antivirals from the same discovery effort <Reference id=42508/>. Both compounds inhibit SARS-CoV-2 3CL protease (Mpro). <Ligand id=11616/> is the other lead.
iupac name: 5-(3-{3-chloro-5-[(2-chlorophenyl)methoxy]-4-fluorophenyl}-2-oxo-2H-[1,3'-bipyridin]-5-yl)-1-methyl-1,2,3,4-tetrahydropyrimidine-2,4-dione
approved: f
ligand name: compound 19 [Zhang et al., 2021]
type: SyntheticOrganicLigand

LY395756
in ch i key: BQVZICWQBFTOJX-QNDZYWSYSA-N
in ch i: InChI=1S/C9H13NO4/c1-3-2-9(10,8(13)14)6-4(3)5(6)7(11)12/h3-6H,2,10H2,1H3,(H,11,12)(H,13,14)/t3-,4+,5+,6+,9+/m1/s1
comment: LY 395756 is a small molecule that acts as an agonist of mGlu2 receptors and as an antagonist of mGlu3 receptors <Reference id=42504/>.
xref: CHEMBL192051
synonym: (±)-LY 395756
synonym: LY39
synonym: LY-395756
synonym: LY 395756
approved: f
ligand name: LY395756
type: SyntheticOrganicLigand

ropsacitinib
canonical SMILES: N#CCC1(CC(C1)C#N)n1ncc(c1)c1nc(cn2c1ccn2)c1cnn(c1)C
isomeric SMILES: N#CCC1(CC(C1)C#N)n1ncc(c1)c1nc(cn2c1ccn2)c1cnn(c1)C
in ch i key: XPLZTJWZDBFWDE-UHFFFAOYSA-N
in ch i: InChI=1S/C20H17N9/c1-27-11-15(9-24-27)17-13-28-18(2-5-23-28)19(26-17)16-10-25-29(12-16)20(3-4-21)6-14(7-20)8-22/h2,5,9-14H,3,6-7H2,1H3
comment: Ropsacitinib (PF-06826647) is claimed as a tyrosine kinase 2 (TYK2) Inhibitor <Reference id=42499/>. However, its activity at clinically relevant concentrations to achieve TYK2 inhibition is suggestive of significant inhibition of at least JAK2, if not also of JAK1 <Reference id=42502/>. Ropsacitinib is an ATP-competitive inhibitor.
iupac name: 3-(cyanomethyl)-3-[4-[6-(1-methylpyrazol-4-yl)pyrazolo[1,5-a]pyrazin-4-yl]pyrazol-1-yl]cyclobutane-1-carbonitrile
xref: CHEMBL4459585
synonym: PF-06826647
synonym: PF06826647
synonym: Tyk2-IN-8
synonym: compound 22 [PMID: 32787094]
approved: f
ligand name: ropsacitinib
type: SyntheticOrganicLigand

CRV431
in ch i key: KBARHGHBFILILC-NGIJKBHDSA-N
comment: CRV431 is a <Ligand id=1024/> analogue in which the amino acids in the cyclosporin ring, which are responsible for immunosuppressive activity, have been modified <Reference id=42494/><Reference id=42498/>. It acts as a pan-cyclophilin inhibitor <Reference id=42495/>, and it is being investigated for clinical efficacy in nonalcoholic steatohepatitis (NASH). Antiviral activity (likely by blocking important virus-host cyclophilin interactions) against hepatitis B and C viruses and HIV-1 has been reported <Reference id=42497/><Reference id=42496/>.
iupac name: N-[(7R,8R)-8-[(2S,5S,8R,11S,14S,17S,20S,23R,26S,29S,32S)-5-ethyl-1,7,8,10,16,20,23,25,28,31-decamethyl-11,17,26,29-tetrakis(2-methylpropyl)-3,6,9,12,15,18,21,24,27,30,33-undecaoxo-14,32-di(propan-2-yl)-1,4,7,10,13,16,19,22,25,28,31-undecazacyclotritriacont-2-yl]-8-hydroxy-7-methyloctyl]acetamide
xref: CHEMBL4297487
synonym: CRV-431
synonym: CPI-431
synonym: CPI431
synonym: CPI-431-32
approved: f
ligand name: CRV431
type: SyntheticOrganicLigand

CGP-37157
canonical SMILES: O=C1CSC(c2c(N1)ccc(c2)Cl)c1ccccc1Cl
isomeric SMILES: O=C1CSC(c2c(N1)ccc(c2)Cl)c1ccccc1Cl
in ch i key: KQEPIRKXSUIUTH-UHFFFAOYSA-N
in ch i: InChI=1S/C15H11Cl2NOS/c16-9-5-6-13-11(7-9)15(20-8-14(19)18-13)10-3-1-2-4-12(10)17/h1-7,15H,8H2,(H,18,19)
comment: CGP-37157 is an inhibitor of the mitochondrial Na+/Ca2+ exchanger NCLX (NKCX6; SLC8B1) <Reference id=42489/>. Drawbacks of this inhibitor include its low efficacy, lack of selectivity and poor aqueous solubility <Reference id=42490/>. Improved CGP-37157 analogues are reported in <Reference id=42490/>.
iupac name: 7-chloro-5-(2-chlorophenyl)-1,5-dihydro-4,1-benzothiazepin-2-one
xref: CHEMBL1495071
synonym: CGP37157
approved: f
ligand name: CGP-37157
type: SyntheticOrganicLigand

pegcantratinib
in ch i key: MTDVEOMKVDOULD-UHFFFAOYSA-N
in ch i: InChI=1S/C32H28N4O7/c1-31-32(29(38)34(30(39)43-32)11-12-41-14-13-40-2)15-22(42-31)35-20-9-5-3-7-17(20)24-25-19(16-33-28(25)37)23-18-8-4-6-10-21(18)36(31)27(23)26(24)35/h3-10,22H,11-16H2,1-2H3,(H,33,37)
comment: Pegcantratinib (CT-327/SNA-120) is a clinical stage agent that inhibits the intracellular kinase domain of tropomyosin-related receptor kinase A (TrkA; NTRK1). TrkA is the high affinity receptor for nerve growth factor (NGF), and is a key target in pruritus, within the NGF-TrkA-TRPV1 pathway. As a TrkA inhibitor pegcantratinib is being evaluated as a potential topical treatment for inflammatory skin conditions. Chemically it is a 2kDa PEG derivative of <Ligand id=336/> that was originally developed by Sienna Biopharmaceuticals. PEG conjugation facilitates the delivery of high levels of the active ingredient to skin cells, and avoids the systemic side effects associated with an orally delivered version of the drug.
synonym: CT-327
synonym: CT327
synonym: SNA-120
synonym: SNA120
synonym: Pegylated K-252
synonym: K-252a-PEG2K
approved: f
ligand name: pegcantratinib
type: SyntheticOrganicLigand

compound 73 [WO2017106607A1]
in ch i key: BJXYHBKEQFQVES-NWDGAFQWSA-N
in ch i: InChI=1S/C16H15F3N4/c17-16(18,19)11-6-12(21)9-23(8-11)14-4-3-10(7-20)15-13(14)2-1-5-22-15/h1-5,11-12H,6,8-9,21H2/t11-,12+/m0/s1
comment: This chemical structure (as the IUPAC name) was obtained from the special release of proposed INNs for COVID-related therapeutics that was published by the WHO in October 2020. The INN structure was identified as being identical to compound 73 from Merck's patent WO2017106607A1 (2017) in which it is claimed as a Toll-like receptor (TLR)7 and TLR8 antagonist for the treatment of immune disorders <Reference id=40893/>. We speculate that this is Merck's clinical lead M5049, which is expected to prevent activation of TLR7/8 which detect single-stranded RNA from viruses including SARS-CoV-2 <Reference id=40894/>. M5049 is administered orally. At the time of generating this entry (Nov 2020) there had been no formal name>structure disclosure of M5049. We will update this record when new details are published.
iupac name: 5-[(3R,5S)-3-amino-5-(trifluoromethyl)piperidin-1-yl]quinoline-8-carbonitrile
synonym: enpatoran (proposed INN)
approved: f
ligand name: compound 73 [WO2017106607A1]
type: SyntheticOrganicLigand

epitinib
in ch i key: DQAZPZIYEOGZAF-UHFFFAOYSA-N
in ch i: InChI=1S/C24H26N6O2/c1-4-17-7-6-8-18(13-17)27-23-19-14-21(22(32-3)15-20(19)25-16-26-23)28-24(31)30-11-9-29(5-2)10-12-30/h1,6-8,13-16H,5,9-12H2,2-3H3,(H,28,31)(H,25,26,27)
comment: Epitinib (HMPL-813) is a selective EGFR tyrosine kinase inhibitor that is under investigation for potential to treat solid tumours in China. Epitinib appears to be a 'pseudo' INN. As of July 2021 there had been no submission to the WHO for the INN. The chemical structure is claimed in patent WO2010002845A2 <Reference id=42480/>.
iupac name: 4-ethyl-N-[4-(3-ethynylanilino)-7-methoxyquinazolin-6-yl]piperazine-1-carboxamide
synonym: HMPL-813
synonym: HMPL813
synonym: compound 68 [WO2010002845A2]
approved: f
ligand name: epitinib
type: SyntheticOrganicLigand

olsalazine
canonical SMILES: OC(=O)c1cc(N=Nc2ccc(c(c2)C(=O)O)O)ccc1O
isomeric SMILES: OC(=O)c1cc(N=Nc2ccc(c(c2)C(=O)O)O)ccc1O
in ch i key: QQBDLJCYGRGAKP-UHFFFAOYSA-N
in ch i: InChI=1S/C14H10N2O6/c17-11-3-1-7(5-9(11)13(19)20)15-16-8-2-4-12(18)10(6-8)14(21)22/h1-6,17-18H,(H,19,20)(H,21,22)
comment: Olsalazine is a prodrug of <Ligand id=2700/>.
iupac name: 5-[(3-carboxy-4-hydroxyphenyl)diazenyl]-2-hydroxybenzoic acid
xref: CHEMBL425
synonym: Dipentum®
synonym: CJ-91B
synonym: CJ91B
approved: t
ligand name: olsalazine
type: SyntheticOrganicLigand

compound 15l [PMID: 34242027]
in ch i key: DVFMRMSQBLLRFB-HRNNMHKYSA-N
in ch i: InChI=1S/C34H43N5O7/c1-18(2)13-26(39-33(43)27-16-23-24(37-27)10-7-11-29(23)45-6)32(42)38-25(15-22-9-8-12-35-31(22)41)28(40)17-46-34(44)30-19(3)14-20(4)36-21(30)5/h7,10-11,14,16,18,22,25-26,37H,8-9,12-13,15,17H2,1-6H3,(H,35,41)(H,38,42)(H,39,43)/t22-,25-,26-/m0/s1
comment: This compound is a covalent inhibitor of SARS-CoV-2 3CL protease (Mpro) <Reference id=42474/>. It is stable in human and mouse plasma, and is not toxic against experimental cell lines (Vero E6 and A549 cells).
iupac name: (3S)-3-{[N-(4-Methoxy-1H-indole-2-carbonyl)-l-leucyl]amino}-2-oxo-4-[(3S)-2-oxopiperidin-3-yl]butyl 2,4,6-Trimethylpyridine-3-carboxylate
approved: f
ligand name: compound 15l [PMID: 34242027]
type: SyntheticOrganicLigand

melphalan flufenamide
in ch i key: YQZNKYXGZSVEHI-VXKWHMMOSA-N
comment: Melphalan flufenamide is a peptide-conjugated prodrug of the cytotoxic DNA alkylating drug <Ligand id=7620/> <Reference id=42473/>. It is highly lipophilic and is rapidly transported into cells where it is quickly hydrolysed by aminopeptidases that are overexpressed by some cancer cells. Melphalan flufenamide is being evaluated as a treatment for multiple myeloma <Reference id=42468/><Reference id=42470/><Reference id=42472/>. The IUPAC Condensed peptide sequence for melphalan flufenamide is H-Phe(Unk)-Phe(4-F)-OEt.
iupac name: ethyl (2S)-2-[[(2S)-2-amino-3-[4-[bis(2-chloroethyl)amino]phenyl]propanoyl]amino]-3-(4-fluorophenyl)propanoate
xref: CHEMBL4303060
synonym: Prodrug J 1
synonym: Melflufen
synonym: Prodrug J-1
synonym: Pepaxto®
approved: t
ligand name: melphalan flufenamide
type: SyntheticOrganicLigand

DX600
in ch i key: KIYFMMDRMKTMJU-JMSLXWMVSA-N
comment: DX600 is a peptide inhibitor of angiotensin-converting enzyme 2 (ACE2) <Reference id=42461/>. It blocks the cardioprotective effect of ACE2, but does not inhibit ACE activity <Reference id=42461/><Reference id=42463/>. A gallium-68 labeled cyclic DX600 derivative can be used as an ACE2 radiotracer <Reference id=42462/> SARS-CoV-2 and COVID-19: Experiments using lab-grown, human embryonic stem cell-derived beating cardiomyocytes have demonstrated that DX600 can prevent pseudotyped SARS-CoV-2 from entering the heart cells <Reference id=42614/>. This research indicates that agents that physically block spike-ACE2 binding could be leveraged as novel infection preventatives, that also offer the potential to reduce SARS-CoV-2-mediated damage to heart tissue.
synonym: DX-600
approved: f
ligand name: DX600
type: PeptideLigand

compound 21 [PMID: 34141085]
in ch i key: QDVBJHFEZRTDHU-QAQDUYKDSA-N
in ch i: InChI=1S/C26H24F3N3O4/c1-15-4-2-7-21-22(15)23(33)32(13-16-8-10-17(11-9-16)24(34)35)25(36)31(21)14-18-5-3-6-20(19(18)12-30)26(27,28)29/h2-7,16-17H,8-11,13-14H2,1H3,(H,34,35)/t16-,17-
comment: Compound 21 is an orally bioavailable tankyrase inhibitor that was designed for antitumour potential <Reference id=42454/>. It is active in vitro against cancer cell lines and in in vivo cancer models.
iupac name: 4-[[1-[[2-cyano-3-(trifluoromethyl)phenyl]methyl]-5-methyl-2,4-dioxoquinazolin-3-yl]methyl]cyclohexane-1-carboxylic acid
xref: CHEMBL3109649
approved: f
ligand name: compound 21 [PMID: 34141085]
type: SyntheticOrganicLigand

SD-91
in ch i key: OHDMEJTVYXXZNQ-OPKPGBGESA-N
in ch i: InChI=1S/C59H62N9O13P/c60-49(69)27-24-44(53(72)65-52(36-14-7-4-8-15-36)37-16-9-5-10-17-37)62-56(75)48-25-22-40-29-30-66(34-46(58(77)68(40)48)63-54(73)45-32-39-31-38(21-23-43(39)61-45)59(78)82(79,80)81)51(71)20-11-3-1-2-6-13-35-18-12-19-41-42(35)33-67(57(41)76)47-26-28-50(70)64-55(47)74/h4-5,7-10,12,14-19,21,23,31-32,40,44,46-48,52,61H,1-3,11,20,22,24-30,33-34H2,(H2,60,69)(H,62,75)(H,63,73)(H,65,72)(H,64,70,74)(H2,79,80,81)/t40-,44+,46+,47?,48+/m1/s1
comment: SD-91 is a selective PROTAC (proteolysis targeting chimaera) degrader of signal transducer and activator of transcription 3 (STAT3) <Reference id=42452/>. It induces significant and long-lasting tumour regression in vivo. It is one of the chemical structures that are claimed as STAT3 degraders in patent WO2020198435A1 from The Regents Of The University Of Michigan <Reference id=42453/>. SD-91 contains an inhibitor molecule that targets the STAT3 SH2 domain that is linked to a cereblon binding moiety that interacts with the cereblon/cullin 4A E3 ligase to promote proteosomal degradation.
iupac name: [2-[[(5S,8S,10aR)-8-[[(2S)-5-amino-1-(benzhydrylamino)-1,5-dioxopentan-2-yl]carbamoyl]-3-[8-[2-(2,6-dioxopiperidin-3-yl)-1-oxo-3H-isoindol-4-yl]oct-7-ynoyl]-6-oxo-1,2,4,5,8,9,10,10a-octahydropyrrolo[1,2-a][1,5]diazocin-5-yl]carbamoyl]-1H-indole-5-carbonyl]phosphonic acid
approved: f
ligand name: SD-91
type: SyntheticOrganicLigand

BMS-741672
in ch i key: GVOISEJVFFIGQE-YCZSINBZSA-N
in ch i: InChI=1S/C25H33F3N6O2/c1-14(2)33(4)17-6-8-22(21(12-17)31-15(3)35)34-10-9-20(24(34)36)32-23-18-11-16(25(26,27)28)5-7-19(18)29-13-30-23/h5,7,11,13-14,17,20-22H,6,8-10,12H2,1-4H3,(H,31,35)(H,29,30,32)/t17-,20+,21-,22+/m1/s1
comment: BMS-741672 is a selective antagonist of CC chemokine receptor 2 (CCR2) <Reference id=42451/>. It is ~700-fold selective for CCR2 vs. CCR5 in vitro.
iupac name: N-[(1R,2S,5R)-5-[methyl(propan-2-yl)amino]-2-[(3S)-2-oxo-3-[[6-(trifluoromethyl)quinazolin-4-yl]amino]pyrrolidin-1-yl]cyclohexyl]acetamide
xref: CHEMBL4442783
synonym: compound 7 [PMID: 30891130]
synonym: BMS741672
synonym: compound 1a [PMID: 34141082]
approved: f
ligand name: BMS-741672
type: SyntheticOrganicLigand

BMS-753426
in ch i key: QAPTWHXHEYAIKG-RCOXNQKVSA-N
in ch i: InChI=1S/C25H33F3N6O2/c1-14(35)31-20-12-16(33-24(2,3)4)6-8-21(20)34-10-9-19(23(34)36)32-22-17-11-15(25(26,27)28)5-7-18(17)29-13-30-22/h5,7,11,13,16,19-21,33H,6,8-10,12H2,1-4H3,(H,31,35)(H,29,30,32)/t16-,19+,20-,21+/m1/s1
comment: BMS-753426 is an orally bioavailable antagonist with activity at CC chemokine receptor 2 (CCR2) and CCR5 <Reference id=42450/>.
iupac name: N-[(1R,2S,5R)-5-(tert-butylamino)-2-[(3S)-2-oxo-3-[[6-(trifluoromethyl)quinazolin-4-yl]amino]pyrrolidin-1-yl]cyclohexyl]acetamide
synonym: compound 2d [PMID: 34141082]
synonym: BMS753426
approved: f
ligand name: BMS-753426
type: SyntheticOrganicLigand

sulfaphenazole
canonical SMILES: Nc1ccc(cc1)S(=O)(=O)Nc1ccnn1c1ccccc1
isomeric SMILES: Nc1ccc(cc1)S(=O)(=O)Nc1ccnn1c1ccccc1
in ch i key: QWCJHSGMANYXCW-UHFFFAOYSA-N
in ch i: InChI=1S/C15H14N4O2S/c16-12-6-8-14(9-7-12)22(20,21)18-15-10-11-17-19(15)13-4-2-1-3-5-13/h1-11,18H,16H2
comment: Sulfaphenazole is a long-acting sulfonamide antibacterial.
iupac name: 4-amino-N-(2-phenylpyrazol-3-yl)benzenesulfonamide
xref: CHEMBL1109
synonym: Sulfabid®
approved: f
ligand name: sulfaphenazole
type: SyntheticOrganicLigand

AZ5104
in ch i key: IQNVEOMHJHBNHC-UHFFFAOYSA-N
in ch i: InChI=1S/C27H31N7O2/c1-6-26(35)30-22-15-23(25(36-5)16-24(22)34(4)14-13-33(2)3)32-27-28-12-11-21(31-27)19-17-29-20-10-8-7-9-18(19)20/h6-12,15-17,29H,1,13-14H2,2-5H3,(H,30,35)(H,28,31,32)
comment: AZ5104 is the demethylated metabolite of the EGFR inhibitor drug <Ligand id=7719/>. It exhibits inhibitory activity against a number of clinically relevant oncogenic EGFR mutants <Reference id=42389/>.
xref: CHEMBL3353411
synonym: AZ-5104
approved: f
ligand name: AZ5104
type: SyntheticOrganicLigand

bilastine
in ch i key: ACCMWZWAEFYUGZ-UHFFFAOYSA-N
in ch i: InChI=1S/C28H37N3O3/c1-4-34-20-19-31-25-8-6-5-7-24(25)29-26(31)22-14-17-30(18-15-22)16-13-21-9-11-23(12-10-21)28(2,3)27(32)33/h5-12,22H,4,13-20H2,1-3H3,(H,32,33)
comment: Bilastine is a non-sedating histamine H1 receptor antagonist/inverse agonist <Reference id=42386/><Reference id=42387/>. A repurposing screen of small molecule drugs discovered that bilastine inhibits SARS-CoV-2 Mpro activity by around 20% (see CHEMBL4495564).
iupac name: 2-[4-[2-[4-[1-(2-ethoxyethyl)benzimidazol-2-yl]piperidin-1-yl]ethyl]phenyl]-2-methylpropanoic acid
xref: CHEMBL1742423
synonym: Ilaxten®
synonym: Bilaxten®
approved: t
ligand name: bilastine
type: SyntheticOrganicLigand

compound 2a [PMID: 34213885]
in ch i key: YHWWOAJOMPQXED-LEDIMMKISA-N
in ch i: InChI=1S/C24H39N3O5/c1-15(2)8-21(23(30)26-20(13-28)12-19-6-7-25-22(19)29)27-24(31)32-14-18-10-16-4-3-5-17(9-16)11-18/h13,15-21H,3-12,14H2,1-2H3,(H,25,29)(H,26,30)(H,27,31)/t16-,17+,18?,19-,20-,21-/m0/s1
comment: Compound 2a is an inhibitor of SARS-CoV-2 3CL protease (Mpro). It is an example from series generated from a structure-guided design study <Reference id=42448/>. Compound 2a also inhibits MERS-CoV Mpro.
iupac name: ((1R,3s,5S)-Bicyclo[3.3.1]nonan-3-yl)methyl ((S)-4-Methyl-1-oxo-1-(((S)-1-oxo-3-((S)-2-oxopyrrolidin-3-yl)propan-2-yl)amino)pentan-2-yl)carbamate
approved: f
ligand name: compound 2a [PMID: 34213885]
type: SyntheticOrganicLigand

compound 18 [PMID: 34212719]
canonical SMILES: C#Cc1ccnc(n1)C#Cc1ccc2c(c1)n(cn2)c1ccnc(n1)N
isomeric SMILES: C#Cc1ccnc(n1)C#Cc1ccc2c(c1)n(cn2)c1ccnc(n1)N
in ch i key: WHGGGFMSJFAYSV-UHFFFAOYSA-N
in ch i: InChI=1S/C19H11N7/c1-2-14-7-9-21-17(24-14)6-4-13-3-5-15-16(11-13)26(12-23-15)18-8-10-22-19(20)25-18/h1,3,5,7-12H,(H2,20,22,25)
comment: Compound 18 is the most potent of a SAR series of covalent inhibitors of NF-κB-inducing kinase (NIK; MAP3K14) <Reference id=42447/>. NIK is a key enzyme in the noncanonical NF-κB pathway. Compound 18 binds irreversibly to Cys444 within the back pocket of the kinase's active site.
iupac name: 4-(6-((4-Ethynylpyrimidin-2-yl)Ethynyl)-1H-Benzo[d]Imidazol-1-yl)Pyrimidin-2-Amine
approved: f
ligand name: compound 18 [PMID: 34212719]
type: SyntheticOrganicLigand

estetrol
in ch i key: AJIPIJNNOJSSQC-NYLIRDPKSA-N
in ch i: InChI=1S/C18H24O4/c1-18-7-6-12-11-5-3-10(19)8-9(11)2-4-13(12)14(18)15(20)16(21)17(18)22/h3,5,8,12-17,19-22H,2,4,6-7H2,1H3/t12-,13-,14-,15-,16-,17+,18+/m1/s1
comment: Estetrol is a natural estrogen that is produced exclusively during pregnancy by the fetal liver. It is produced synthetically (from a plant source) for medicinal use. Estetrol has tissue selective actions <Reference id=42430/><Reference id=42429/>, with estrogenic activity in the uterus, vagina and endometrium and estrogen antagonist activity in breast tissue.
iupac name: (8R,9S,13S,14S,15R,16R,17R)-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-3,15,16,17-tetrol
xref: CHEMBL1230314
synonym: 15 alpha-hydroxyestriol
synonym: 15 α-hydroxyestriol
synonym: Lydisilka® (EMA); ; estetrol monohydrate + drospirenone
synonym: E4
synonym: Nextstellis® (US); estetrol monohydrate + drospirenone
synonym: Drovelis® (EMA); ; estetrol monohydrate + drospirenone
approved: t
ligand name: estetrol
type: SyntheticOrganicLigand

BIO-32546
in ch i key: PZASAAIJIFDWSB-CKPDSHCKSA-N
in ch i: InChI=1S/C28H31F6NO3/c1-15(35-20-7-8-21(35)13-18(12-20)26(36)37)17-3-2-16-4-11-24(25(23(16)14-17)28(32,33)34)38-22-9-5-19(6-10-22)27(29,30)31/h2-4,11,14-15,18-22H,5-10,12-13H2,1H3,(H,36,37)/t15-,18?,19?,20?,21?,22?/m0/s1
comment: BIO-32546 is an autotaxin (ENPP2) inhibitor from Biogen <Reference id=42427/>. Autotaxin inhibitors are used to reduce LPA biosynthesis for anti-inflammatory effect. BIO-32546 shows efficacy in a rat complete Freund's adjuvant (CFA) rheumatoid arthritis model.
iupac name: 8-[(1S)-1-[8-(trifluoromethyl)-7-[4-(trifluoromethyl)cyclohexyl]oxynaphthalen-2-yl]ethyl]-8-azabicyclo[3.2.1]octane-3-carboxylic acid
synonym: example 12a [WO2014018881A1]
synonym: BIO32546
approved: f
ligand name: BIO-32546
type: SyntheticOrganicLigand

compound 20c [PMID: 34181850]
in ch i key: SPVXUJWQZXMNES-UHFFFAOYSA-N
comment: Compound 20c is a mucosa-associated lymphoid tissue lymphoma translocation protein 1 (MALT1) inhibitor <Reference id=42425/>. It was designed to provide antitumour efficacy against B cell lymphoma.
iupac name: 4-(2-Chloroacetamido)-N-(2,5-dimethoxyphenyl)-2-thioxo-3-(4-(trifluoromethyl)phenyl)-2,3-dihydrothiazole-5-carboxamide
approved: f
ligand name: compound 20c [PMID: 34181850]
type: SyntheticOrganicLigand

compound 17 [PMID: 34176264]
in ch i key: UMEMOEKJTJMMJN-UHFFFAOYSA-N
in ch i: InChI=1S/C40H37N7O6/c1-4-22-17-25-26(40(2,3)36-34(35(25)50)23-9-8-21(19-41)16-28(23)43-36)18-30(22)45-12-14-46(15-13-45)32(49)20-42-27-7-5-6-24-33(27)39(53)47(38(24)52)29-10-11-31(48)44-37(29)51/h5-9,16-18,29,42-43H,4,10-15,20H2,1-3H3,(H,44,48,51)
comment: Compound 17 is an <Ligand id=7739/>-based PROTAC degrader of anaplastic lymphoma kinase (ALK) <Reference id=42423/>. The alectinib analogue is conjugated to <Ligand id=7348/> through a linker, to deliver ALK protein for degradation via the ubiquitously expressed E3 ligase receptor cereblon. Compound 17 is one of the chemical structures claimed in ShanghaiTech University's patent WO2019114770A1 <Reference id=42424/>.
iupac name: 8-[4-[2-[[2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-4-yl]amino]acetyl]piperazin-1-yl]-9-ethyl-6,6-dimethyl-11-oxo-5H-benzo[b]carbazole-3-carbonitrile
approved: f
ligand name: compound 17 [PMID: 34176264]
type: SyntheticOrganicLigand

balixafortide
in ch i key: OYWQJZAVFWOOBF-WBMPNIIXSA-N
comment: Balixafortide (POL6326) is an orally bioavailable cyclic peptide antagonist of the CXC chemokine receptor 4 (CXCR4). The CXCR4/SDF-1 axis regulates function and trafficking of immune cells. Balixafortid blocks interaction of the receptor with its ligand CXCL12 (SDF-1) <Reference id=42415/>. Disrupting the SDF-1/CXCR4 interaction is ubeing exploited for mobilisation and harvesting of peripheral blood HSCs for transplant procedures, and in cancer therapy for antimetastatic activity (by dislodging stem cells from the bone marrow). The peptide structure is cyclo[L-alanyl-L-cysteinyl-L-seryl-L-alanyl-D-prolyl-(2S)-2,4-diaminobutanoyl-L-arginyl-L-tyrosyl-L-cysteinyl-L-tyrosyl-L-glutaminyl-L-lysyl-D-prolyl-L-prolyl-L-tyrosyl-L-histidyl](2-9)-disulfide (from the INN record for balixafortide).
synonym: POL6326
synonym: POL-6326
approved: f
ligand name: balixafortide
type: PeptideLigand

blarcamesine
canonical SMILES: CN(CC1CCOC1(c1ccccc1)c1ccccc1)C
isomeric SMILES: CN(CC1CCOC1(c1ccccc1)c1ccccc1)C
in ch i key: BOTHKNZTGGXFEQ-UHFFFAOYSA-N
in ch i: InChI=1S/C19H23NO/c1-20(2)15-18-13-14-21-19(18,16-9-5-3-6-10-16)17-11-7-4-8-12-17/h3-12,18H,13-15H2,1-2H3
comment: Blarcamesine (Anavex2-73) is a Sigma-1 (σ1) protein agonist and muscarinic acetylcholine receptor modulator <Reference id=42408/>. Anavex are investigating it for potential to slow progression in neurodegenerative conditions including Parkinson's and Alzheimer's diseases, and Rett syndrome <Reference id=42407/>. Anticonvulsant, anti-amnesic, neuroprotective and antidepressant activities in response to blarcamesine have been identified in a number of animal models of neurodegenerative and neurodevelopmental conditions <Reference id=42408/><Reference id=42409/><Reference id=42410/><Reference id=42411/>.
iupac name: 1-(2,2-diphenyloxolan-3-yl)-N,N-dimethylmethanamine
xref: CHEMBL4297224
synonym: Anavex 2-73
synonym: Anavex2-73
synonym: THD-DP-FM
synonym: AE-37
synonym: AE37
approved: f
ligand name: blarcamesine
type: SyntheticOrganicLigand

PCI-27483
in ch i key: WDJHHCAKBRKCLW-IBGZPJMESA-N
in ch i: InChI=1S/C26H24N6O9S/c27-24(28)12-1-3-17-18(8-12)32-25(31-17)16-6-11(7-21(34)30-19(26(38)39)10-22(35)36)5-15(23(16)37)14-9-13(42(29,40)41)2-4-20(14)33/h1-6,8-9,19,33,37H,7,10H2,(H3,27,28)(H,30,34)(H,31,32)(H,35,36)(H,38,39)(H2,29,40,41)/t19-/m0/s1
comment: PCI-27483 is a small molecule inhibitor of activated factor VII (FVIIa). A complex of FVIIa and tissue factor are involved in promoting cell migration and angiogenesis and may contribute to tumour invasiveness via this mechanism. Inhibiting FVIIa is being investigated for anti-tumour potential <Reference id=42405/>.
xref: CHEMBL4297315
synonym: PCI27483
synonym: Example 1 [WO2005118554A2]
approved: f
ligand name: PCI-27483
type: SyntheticOrganicLigand

avoralstat
in ch i key: TUWMKPVJGGWGNL-UHFFFAOYSA-N
in ch i: InChI=1S/C28H27N5O5/c1-3-16-12-21(26(34)32-18-8-6-17(7-9-18)25(29)30)20(13-23(16)38-2)19-10-11-22(33-24(19)28(36)37)27(35)31-14-15-4-5-15/h3,6-13,15H,1,4-5,14H2,2H3,(H3,29,30)(H,31,35)(H,32,34)(H,36,37)
comment: Avoralstat (BCX-4161) is a small molecule, oral plasma kallikrein (a serine protease that generates bradykinin from kininogen) inhibitor <Reference id=42402/>. Data pubished in 2021 indicate that avoralstat inhibits TMPRSS2 (a protease required for spike protein-mediated SARS-CoV-2 viral entry via ACE2) with comparable inhibitory activity to <Ligand id=6432/> <Reference id=42400/>.
iupac name: 3-[2-[(4-carbamimidoylphenyl)carbamoyl]-4-ethenyl-5-methoxyphenyl]-6-(cyclopropylmethylcarbamoyl)pyridine-2-carboxylic acid
xref: CHEMBL4297502
synonym: BCX-4161
synonym: BCX4161
approved: f
ligand name: avoralstat
type: SyntheticOrganicLigand

anagliptin
in ch i key: LDXYBEHACFJIEL-HNNXBMFYSA-N
in ch i: InChI=1S/C19H25N7O2/c1-13-7-16-21-9-14(11-26(16)24-13)18(28)22-12-19(2,3)23-10-17(27)25-6-4-5-15(25)8-20/h7,9,11,15,23H,4-6,10,12H2,1-3H3,(H,22,28)/t15-/m0/s1
comment: Anagliptin (SkK-0403) is a dipeptidyl peptidase-4 (DPP4) inhibitor <Reference id=42395/>.
xref: CHEMBL1929396
synonym: SK-0403
synonym: Suiny®
synonym: SK0403
synonym: CWP-403
synonym: compound 4a [PMID: 22019046]
approved: t
ligand name: anagliptin
type: SyntheticOrganicLigand

udenafil
in ch i key: IYFNEFQTYQPVOC-UHFFFAOYSA-N
in ch i: InChI=1S/C25H36N6O4S/c1-5-8-20-22-23(31(4)29-20)25(32)28-24(27-22)19-16-18(10-11-21(19)35-15-6-2)36(33,34)26-13-12-17-9-7-14-30(17)3/h10-11,16-17,26H,5-9,12-15H2,1-4H3,(H,27,28,32)
comment: Udenafil (DA-8159) is an oral PDE5 inhibitor that was developed by Dong-A Pharmaceutical Company for erectogenic potential <Reference id=42384/><Reference id=42382/><Reference id=42383/>.
iupac name: 3-(1-methyl-7-oxo-3-propyl-6H-pyrazolo[4,3-d]pyrimidin-5-yl)-N-[2-(1-methylpyrrolidin-2-yl)ethyl]-4-propoxybenzenesulfonamide
xref: CHEMBL2103849
synonym: DA-8159
synonym: DA8159
synonym: Zydena®
approved: t
ligand name: udenafil
type: SyntheticOrganicLigand

zucapsaicin
canonical SMILES: COc1cc(CNC(=O)CCCC/C=C/C(C)C)ccc1O
isomeric SMILES: COc1cc(CNC(=O)CCCC/C=C/C(C)C)ccc1O
in ch i key: YKPUWZUDDOIDPM-VURMDHGXSA-N
in ch i: InChI=1S/C18H27NO3/c1-14(2)8-6-4-5-7-9-18(21)19-13-15-10-11-16(20)17(12-15)22-3/h6,8,10-12,14,20H,4-5,7,9,13H2,1-3H3,(H,19,21)/b8-6-
comment: Zucapsaicin is the cis-isomer of <Ligand id=2486/>. It is a TRPV1 agonist <Reference id=42381/>.
iupac name: (Z)-N-[(4-hydroxy-3-methoxyphenyl)methyl]-8-methylnon-6-enamide
xref: CHEMBL313971
synonym: Civanex®
synonym: Zuacta®
approved: t
ligand name: zucapsaicin
type: SyntheticOrganicLigand

bictegravir
in ch i key: SOLUWJRYJLAZCX-LYOVBCGYSA-N
in ch i: InChI=1S/C21H18F3N3O5/c22-9-3-14(23)12(15(24)4-9)6-25-20(30)13-7-26-8-16-27(10-1-2-11(5-10)32-16)21(31)17(26)19(29)18(13)28/h3-4,7,10-11,16,29H,1-2,5-6,8H2,(H,25,30)/t10-,11+,16+/m0/s1
comment: Bictegravir (GS-9883) is an HIV antiviral integrase strand transfer inhibitor. It is structurally related to <Ligand id=7365/>.
xref: CHEMBL3989866
synonym: GS-9883
synonym: GS9883
approved: t
ligand name: bictegravir
type: SyntheticOrganicLigand

elvitegravir
in ch i key: JUZYLCPPVHEVSV-LJQANCHMSA-N
in ch i: InChI=1S/C23H23ClFNO5/c1-12(2)19(11-27)26-10-16(23(29)30)22(28)15-8-14(20(31-3)9-18(15)26)7-13-5-4-6-17(24)21(13)25/h4-6,8-10,12,19,27H,7,11H2,1-3H3,(H,29,30)/t19-/m1/s1
comment: Elvitegravir (GS-9137) is an HIV integrase inhibitor antiretroviral drug <Reference id=42378/>.
xref: CHEMBL204656
synonym: GS-9137
synonym: GS9137
synonym: JTK-303
synonym: JTK303
synonym: Vitekta®
synonym: EVG
synonym: compound 2 [PMID: 18281931]
approved: t
ligand name: elvitegravir
type: SyntheticOrganicLigand

grazoprevir
in ch i key: OBMNJSNZOWALQB-NCQNOWPTSA-N
in ch i: InChI=1S/C38H50N6O9S/c1-6-22-19-38(22,35(47)43-54(49,50)25-13-14-25)42-32(45)29-18-24-20-44(29)34(46)31(37(2,3)4)41-36(48)53-30-16-21(30)10-8-7-9-11-27-33(52-24)40-28-17-23(51-5)12-15-26(28)39-27/h6,12,15,17,21-22,24-25,29-31H,1,7-11,13-14,16,18-20H2,2-5H3,(H,41,48)(H,42,45)(H,43,47)/t21-,22-,24-,29+,30-,31-,38-/m1/s1
comment: Grazoprevir (MK-5172) is an HCV NS3/4A protease inhibitor class antiviral drug <Reference id=42377/>. In vitro evidence of activity against SARS-CoV-2 helicase <Reference id=42374/> and papain-like protease (PLpro) <Reference id=42375/>.
xref: CHEMBL2063090
synonym: MK-5172
synonym: MK5172
synonym: Zepatier® [elbasvir (NS5A inhibitor) + grazoprevir]
synonym: analog 15 [PMID: 24900473]
approved: t
ligand name: grazoprevir
type: SyntheticOrganicLigand

narlaprevir
in ch i key: RICZEKWVNZFTNZ-LFGITCQGSA-N
in ch i: InChI=1S/C36H61N5O7S/c1-10-11-15-24(27(42)30(44)37-22-16-17-22)38-29(43)26-25-23(35(25,8)9)20-41(26)31(45)28(33(2,3)4)39-32(46)40-36(18-13-12-14-19-36)21-49(47,48)34(5,6)7/h22-26,28H,10-21H2,1-9H3,(H,37,44)(H,38,43)(H2,39,40,46)/t23-,24-,25-,26-,28+/m0/s1
comment: Narlaprevir (SCH90051) is an oral HCV NS3 serine protease inhibitor <Reference id=42372/><Reference id=42373/>. It is structurally related to <Ligand id=7876/>. Narlaprevir forms a reversible covalent bond with the protease's active-site serine. It has also been reported to inhibit SARS-CoV-2 coronavirus main cysteine protease (3CLpro or Mpro) in vitro <Reference id=42371/>.
iupac name: narlaprevir
xref: CHEMBL1255891
synonym: Arlansa®
synonym: SCH 900518
synonym: SCH-900518
synonym: SCH900518
approved: t
ligand name: narlaprevir
type: SyntheticOrganicLigand

raltegravir
in ch i key: CZFFBEXEKNGXKS-UHFFFAOYSA-N
in ch i: InChI=1S/C20H21FN6O5/c1-10-25-26-17(32-10)16(30)24-20(2,3)19-23-13(14(28)18(31)27(19)4)15(29)22-9-11-5-7-12(21)8-6-11/h5-8,28H,9H2,1-4H3,(H,22,29)(H,24,30)
comment: Raltegravir (MK-0518) is an HIV integrase inhibitor (integrase strand transfer inhibitor) <Reference id=42370/>.
xref: CHEMBL254316
synonym: Isentress®
synonym: MK-0518
synonym: MK0518
approved: t
ligand name: raltegravir
type: SyntheticOrganicLigand

vaniprevir
in ch i key: KUQWGLQLLVFLSM-ONAXAZCASA-N
in ch i: InChI=1S/C38H55N5O9S/c1-7-25-18-38(25,33(46)41-53(49,50)27-14-15-27)40-31(44)29-17-26-20-43(29)32(45)30(36(2,3)4)39-34(47)51-22-37(5,6)16-9-8-11-23-12-10-13-24-19-42(21-28(23)24)35(48)52-26/h10,12-13,25-27,29-30H,7-9,11,14-22H2,1-6H3,(H,39,47)(H,40,44)(H,41,46)/t25-,26-,29+,30-,38-/m1/s1
comment: Vaniprevir (MK-7009) is a non-covalent competitive, macrocyclic hepatitis C virus (HCV, genotype 1a and 1b) NS3/4A protease inhibitor <Reference id=42368/><Reference id=42369/>. It has also been reported to inhibit SARS CoV-2 papain-like protease (PL-pro) in vitro <Reference id=42110/>.
iupac name: (1R,21S,24S)-21-tert-butyl-N-[(1R,2R)-1-(cyclopropylsulfonylcarbamoyl)-2-ethylcyclopropyl]-16,16-dimethyl-3,19,22-trioxo-2,18-dioxa-4,20,23-triazatetracyclo[21.2.1.14,7.06,11]heptacosa-6(11),7,9-triene-24-carboxamide
xref: CHEMBL4525964
synonym: Vanihep®
synonym: MK-7009
synonym: MK7009
synonym: analog 35b [PMID: 20163176]
approved: t
ligand name: vaniprevir
type: SyntheticOrganicLigand

balsalazide
in ch i key: IPOKCKJONYRRHP-UHFFFAOYSA-N
in ch i: InChI=1S/C17H15N3O6/c21-14-6-5-12(9-13(14)17(25)26)20-19-11-3-1-10(2-4-11)16(24)18-8-7-15(22)23/h1-6,9,21H,7-8H2,(H,18,24)(H,22,23)(H,25,26)
comment: Balsalazide is a prodrug of the anti-inflammatory drug mesalazine.
iupac name: 5-[[4-(2-carboxyethylcarbamoyl)phenyl]diazenyl]-2-hydroxybenzoic acid
xref: CHEMBL1208641
synonym: Colazide®
synonym: Colazal®
synonym: Giazo®
approved: t
ligand name: balsalazide
type: SyntheticOrganicLigand

LUT014
in ch i key: FZPYULHBUBXPIG-UHFFFAOYSA-N
in ch i: InChI=1S/C27H19F3N8O/c1-15-7-8-19-18(9-11-32-24(19)37-16-4-2-5-17(12-16)39-27(28,29)30)21(15)38-25-20(6-3-10-31-25)22-23-26(35-13-33-22)36-14-34-23/h2-14H,1H3,(H,31,38)(H,32,37)(H,33,34,35,36)
comment: LUT014 is a BRAF inhibitor <Reference id=42313/>. BRAF is a component of the signalling pathway utilised by the EGFR. Inhibiting mutant BRAF in cancer cells leads to tumour shrinkage, whereas in normal cells the mitogen-activated protein kinase (MAPK) pathway is activated and proliferation is induced. This latter paradoxical effect of BRAF inhibition is being exploited to reverse inhibition of the MAPK pathway by EGFR inhibitors which is responsible for dose-limiting skin toxicity (acneiform rash) in patients treated with EGFR-targeting anti-tumour agents such as <Ligand id=6882/> or <Ligand id=6883/>.
iupac name: 6-methyl-5-N-[3-(7H-purin-6-yl)pyridin-2-yl]-1-N-[3-(trifluoromethoxy)phenyl]isoquinoline-1,5-diamine
synonym: LUT-014
approved: f
ligand name: LUT014
type: SyntheticOrganicLigand

GDC-0134
in ch i key: SKMKJBYBPYBDMN-RYUDHWBXSA-N
in ch i: InChI=1S/C19H20F4N6O2/c20-17(21)31-14-3-10(6-25-16(14)24)13-5-15(29-7-12-4-11(29)8-30-12)27-18(26-13)28-2-1-19(22,23)9-28/h3,5-6,11-12,17H,1-2,4,7-9H2,(H2,24,25)/t11-,12-/m0/s1
comment: GDC-0134 is a dual leucine zipper kinase (DLK) inhibitor <Reference id=41958/>. It was developed by Genentech for the treatment of amyotrophic lateral sclerosis (ALS, a.k.a. motor neurone disease, MND). GDC-0134 was proposed to decrease disease progression. The chemical structure shown here wasdrawn using Marvin JS (ChemAxon), which gave SMILES that resolve to the PubChem CID listed below. Other drawring tools my produce SMILES that generate an InChiKey with an alternative stereo layer.
xref: CHEMBL3732012
synonym: GDC0134
synonym: compound 279 [WO2014177060A1]
approved: f
ligand name: GDC-0134
type: SyntheticOrganicLigand

analog 18 [PMID: 28696697]
in ch i key: XAZZJHQEPVCAEX-RRTYAWIHSA-N
in ch i: InChI=1S/C26H47N3O5/c1-8-10-12-14-21(30)29-22(18(5)6)25(33)27-19(13-11-9-2)24(32)28-20(15-17(3)4)23(31)26(7)16-34-26/h17-20,22H,8-16H2,1-7H3,(H,27,33)(H,28,32)(H,29,30)/t19-,20-,22+,26+/m0/s1
comment: Analog 18 is the lead from a class of antimalarial compounds based on the naturally derived tripeptide molecule carmaphycin B <Reference id=42302/>. Functionally these compounds inhibit the Plasmodium proteasome. The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY
iupac name: (2S)-2-[[(2R)-2-(hexanoylamino)-3-methylbutanoyl]amino]-N-[(2S)-4-methyl-1-[(2R)-2-methyloxiran-2-yl]-1-oxopentan-2-yl]hexanamide
xref: CHEMBL4086345
approved: f
ligand name: analog 18 [PMID: 28696697]
type: SyntheticOrganicLigand

LY2077855
canonical SMILES: Fc1ccc(cc1)Cc1nnnn1C(=O)N(C)C
isomeric SMILES: Fc1ccc(cc1)Cc1nnnn1C(=O)N(C)C
in ch i key: CKOZVEHVVHCMGD-UHFFFAOYSA-N
in ch i: InChI=1S/C11H12FN5O/c1-16(2)11(18)17-10(13-14-15-17)7-8-3-5-9(12)6-4-8/h3-6H,7H2,1-2H3
comment: LY2077855 is an inhibitor of fatty acid amide hydrolase (FAAH) activity. It is one of the compounds claimed in patent WO2009117444 'Inhibitors of fatty acid amide hydrolase and monoacylglycerol lipase for modulation of cannabinoid receptors' <Reference id=30473/>.
iupac name: 5-[(4-fluorophenyl)methyl]-N,N-dimethyl-1H-1,2,3,4-tetrazole-1-carboxamide
synonym: example 66a [WO2009117444]
approved: f
ligand name: LY2077855
type: SyntheticOrganicLigand

EB-42486
in ch i key: KHSAHYKLUPESPP-UHFFFAOYSA-N
in ch i: InChI=1S/C22H22N8O/c1-13-18(22(2,3)30-21(29(13)4)26-27-28-30)20(31)23-15-10-11-17-16(12-15)19(25-24-17)14-8-6-5-7-9-14/h5-12H,1-4H3,(H,23,31)(H,24,25)
comment: EB-42486 is a potent, oral inhibitor of leucine-rich repeat kinase 2 (LRRK2) G2019S variant that was developed by Escape Bio <Reference id=42300/>. LRRK2G2019S has been identified as an inherited risk variant for developing Parkinson's disease.
synonym: compound 31 [PMID: 33197196]
approved: f
ligand name: EB-42486
type: SyntheticOrganicLigand

compound 13ac [PMID: 33256400]
in ch i key: SURRDPSGERGIIM-VOTSOKGWSA-N
in ch i: InChI=1S/C26H33N7O/c1-18(2)33-17-22(15-28-33)25-19(3)14-27-26(30-25)29-23-9-8-21-16-32(12-10-20(21)13-23)24(34)7-6-11-31(4)5/h6-9,13-15,17-18H,10-12,16H2,1-5H3,(H,27,29,30)/b7-6+
comment: Compound 13ac is reported as a Janus kinase 2 (JAK2) inhibitor, with potent in vivo antitumour efficacy in a xenograft model <Reference id=42299/>.
iupac name: (2E)-4-(dimethylamino)-1-[6-({5-methyl-4-[1-(propan-2-yl)-1H-pyrazol-4-yl]pyrimidin-2-yl}amino)-1,2,3,4-tetrahydroisoquinolin-2-yl]but-2-en-1-one
approved: f
ligand name: compound 13ac [PMID: 33256400]
type: SyntheticOrganicLigand

irigenol
in ch i key: DFURNQJNFBMYHM-UHFFFAOYSA-N
in ch i: InChI=1S/C15H10O8/c16-7-1-5(2-8(17)13(7)20)6-4-23-10-3-9(18)14(21)15(22)11(10)12(6)19/h1-4,16-18,20-22H
comment: This compound is reported as an inhibitor of RGS17 <Reference id=42198/>. It is a plant-derived hexahydroxy flavonoid.
iupac name: 5,6,7-trihydroxy-3-(3,4,5-trihydroxyphenyl)chromen-4-one
xref: CHEMBL1438439
synonym: compound 4 [PMID: 28621943]
approved: f
ligand name: irigenol
type: NaturalProductLigand

compound 1 [PMID: 28621943]
in ch i key: INVGWHRKADIJHF-UHFFFAOYSA-N
in ch i: InChI=1S/C20H14NO4/c1-21-8-15-12(4-5-16-20(15)25-10-22-16)13-3-2-11-6-17-18(24-9-23-17)7-14(11)19(13)21/h2-8H,9-10H2,1H3/q+1
comment: This compound is reported as an inhibitor of RGS17 <Reference id=42198/>. It is a naturally occurring, toxic plant-derived alkaloid.
xref: CHEMBL417799
synonym: sanguinarin
synonym: pseudochelerythrine
synonym: Sanguinarine
approved: f
ligand name: compound 1 [PMID: 28621943]
type: NaturalProductLigand

compound V [PMID: 29351497]
in ch i key: YTVRQZGDIKFCPL-UHFFFAOYSA-N
in ch i: InChI=1S/C25H27N3O3S/c1-25(2,3)17-10-8-16(9-11-17)23(29)26-19-13-20-21(28(5)24(30)27(20)4)14-22(19)32-15-18-7-6-12-31-18/h6-14H,15H2,1-5H3,(H,26,29)
comment: This compound is reported as an inhibitor of RGS17 <Reference id=42197/>.
iupac name: 4-tert-butyl-N-[6-(furan-2-ylmethylsulfanyl)-1,3-dimethyl-2-oxobenzimidazol-5-yl]benzamide
approved: f
ligand name: compound V [PMID: 29351497]
type: SyntheticOrganicLigand

compound IV [PMID: 29351497]
in ch i key: OBTZDIRUQWFRFZ-UHFFFAOYSA-N
in ch i: InChI=1S/C22H18N2O2/c1-14-7-10-16(11-8-14)23-22(25)18-13-20(21-12-9-15(2)26-21)24-19-6-4-3-5-17(18)19/h3-13H,1-2H3,(H,23,25)
comment: This compound is reported as an inhibitor of RGS17 <Reference id=42197/>.
iupac name: 2-(5-methylfuran-2-yl)-N-(4-methylphenyl)quinoline-4-carboxamide
xref: CHEMBL1503727
approved: f
ligand name: compound IV [PMID: 29351497]
type: SyntheticOrganicLigand

compound III [PMID: 29351497]
canonical SMILES: CCOC(=O)/C=C/SC(=C(C(=O)N)C#N)S/C=C/C(=O)OCC
isomeric SMILES: CCOC(=O)/C=C/SC(=C(C(=O)N)C#N)S/C=C/C(=O)OCC
in ch i key: NLFBCYMMUAKCPC-KQQUZDAGSA-N
in ch i: InChI=1S/C14H16N2O5S2/c1-3-20-11(17)5-7-22-14(10(9-15)13(16)19)23-8-6-12(18)21-4-2/h5-8H,3-4H2,1-2H3,(H2,16,19)/b7-5+,8-6+
comment: This compound is reported as an inhibitor of RGS17 <Reference id=42197/>. It contains a substructure that is predicted to behave as a pan assay interference (PAIN) compound.
iupac name: ethyl (E)-3-[3-amino-2-cyano-1-[(E)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate
approved: f
ligand name: compound III [PMID: 29351497]
type: SyntheticOrganicLigand

compound II [PMID: 29351497]
in ch i key: HTSGKJQDMSTCGS-UHFFFAOYSA-N
in ch i: InChI=1S/C23H18Cl2O4S/c1-15-2-12-20(13-3-15)30(28,29)22(23(27)17-6-10-19(25)11-7-17)14-21(26)16-4-8-18(24)9-5-16/h2-13,22H,14H2,1H3
comment: This compound is reported as an inhibitor of RGS17 <Reference id=42197/>.
iupac name: 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione
approved: f
ligand name: compound II [PMID: 29351497]
type: SyntheticOrganicLigand

compound I [PMID: 29351497]
canonical SMILES: O=C(/C=C/c1ccc(o1)C)NCC(CNC(=O)/C=C/c1ccc(o1)C)(C)C
isomeric SMILES: O=C(/C=C/c1ccc(o1)C)NCC(CNC(=O)/C=C/c1ccc(o1)C)(C)C
in ch i key: TVCXEKBERMLWAZ-WGDLNXRISA-N
in ch i: InChI=1S/C21H26N2O4/c1-15-5-7-17(26-15)9-11-19(24)22-13-21(3,4)14-23-20(25)12-10-18-8-6-16(2)27-18/h5-12H,13-14H2,1-4H3,(H,22,24)(H,23,25)/b11-9+,12-10+
comment: This compound is reported as an inhibitor of RGS17 <Reference id=42197/>. It contains a substructure that is predicted to behave as a pan assay interference (PAIN) compound.
iupac name: (E)-N-[2,2-dimethyl-3-[[(E)-3-(5-methylfuran-2-yl)prop-2-enoyl]amino]propyl]-3-(5-methylfuran-2-yl)prop-2-enamide
approved: f
ligand name: compound I [PMID: 29351497]
type: SyntheticOrganicLigand

LY3202626
in ch i key: VQSRKMNBWMHJKY-YTEVENLXSA-N
comment: LY3202626 is a CNS-penetrant beta-secretase 1 (BACE1) inhibitor <Reference id=42195/>. It was designed to mitigate ocular and liver toxicity problems that led to termination of previous clinical BACE1 inhibitor development programmes (<Ligand id=6936/> and <Ligand id=6475/> respectively).
xref: CHEMBL4452566
synonym: compound 22 [PMID: 34081466]
synonym: LY-3202626
approved: f
ligand name: LY3202626
type: SyntheticOrganicLigand

brincidofovir
in ch i key: WXJFKKQWPMNTIM-VWLOTQADSA-N
comment: Brincidofovir is an orally bioavailable, lipid-conjugated (to enhance cellular penetration) ester prodrug of the acyclic nucleoside monophosphate antiviral cidofovir. The active metabolite is cidofovir diphosphate, which disrupts viral DNA polymerase activity and viral DNA replication. Brincidofovir has been investigated for infections caused by several virus families, including cytomegalovirus (CMV), BK virus (BKV), adenoviruses (AdV) <Reference id=42173/>, HPV <Reference id=42171/>, and Epstein-Barr virus (EBV), as well as for smallpox (Variola) infections. A molecular docking study has indicated that brincidofovir interacts with both host ACE2 and SARS-CoV-2 3C-like (main) protease <Reference id=42174/>. Further studies would be required to validate brincidofovir as a potential therapy for SARS-CoV-2 infection.
iupac name: [(2S)-1-(4-amino-2-oxopyrimidin-1-yl)-3-hydroxypropan-2-yl]oxymethyl-(3-hexadecoxypropoxy)phosphinic acid
xref: CHEMBL203321
synonym: Tembexa®
synonym: CMX001
synonym: CMX-001
synonym: HDP-CDV
synonym: hexadecyloxypropyl cidofovir
approved: t
ligand name: brincidofovir
type: SyntheticOrganicLigand

diABZI-4
canonical SMILES: COc1cc(cc2c1n(C/C=C/Cn1/c(=N/C(=O)c3cc(nn3CC)C)/[nH]c3c1c(OCCCN(C)C)cc(c3)C(=O)N)/c(=N/C(=O)c1cc(nn1CC)C)/[nH]2)C(=O)N
isomeric SMILES: COc1cc(cc2c1n(C/C=C/Cn1/c(=N/C(=O)c3cc(nn3CC)C)/[nH]c3c1c(OCCCN(C)C)cc(c3)C(=O)N)/c(=N/C(=O)c1cc(nn1CC)C)/[nH]2)C(=O)N
in ch i key: MXHZAYVEIKSPIA-ZHACJKMWSA-N
in ch i: InChI=1S/C40H49N13O6/c1-8-52-29(17-23(3)47-52)37(56)45-39-43-27-19-25(35(41)54)21-31(58-7)33(27)50(39)14-10-11-15-51-34-28(20-26(36(42)55)22-32(34)59-16-12-13-49(5)6)44-40(51)46-38(57)30-18-24(4)48-53(30)9-2/h10-11,17-22H,8-9,12-16H2,1-7H3,(H2,41,54)(H2,42,55)(H,43,45,56)(H,44,46,57)/b11-10+
comment: DiABZI-4 is a non-dinucleotide STING agonist <Reference id=42164/>. It has been shown to protect against SARS-CoV-2 infection in cells and in vivo in the K18-ACE2-transgenic mouse infection model. The compound is active via intranasal delivery. Its chemical structure is claimed in the same GSK patent as <Ligand id=10128/> (diABZI STING agonist-1) <Reference id=36348/>.
iupac name: 1-[(E)-4-[5-carbamoyl-7-[3-(dimethylamino)propoxy]-2-[(2-ethyl-5-methylpyrazole-3-carbonyl)amino]benzimidazol-1-yl]but-2-enyl]-2-[(2-ethyl-5-methylpyrazole-3-carbonyl)amino]-7-methoxybenzimidazole-5-carboxamide
synonym: diABZI-4
synonym: Example 39 [WO2017175147A1]
approved: f
ligand name: diABZI-4
type: SyntheticOrganicLigand

DSM705
in ch i key: JUBPRXDFKLPILK-LLVKDONJSA-N
in ch i: InChI=1S/C19H19F3N6O/c1-10-13(8-24-15(10)17(29)27-11(2)16-25-9-26-28-16)18(5-6-18)12-3-4-14(23-7-12)19(20,21)22/h3-4,7-9,11,24H,5-6H2,1-2H3,(H,27,29)(H,25,26,28)/t11-/m1/s1
comment: DSM705 is a lead from a pyrrole-based series of antimalarial compounds that inhibit P. falciparum dihydroorotate dehydrogenase (PfDHODH) <Reference id=42390/>. This series of PfDHODH inhibitors could provide a potential backup candidate, with an alternative scaffold, to the clinical lead DSM265.
iupac name: 3-methyl-N-[(1R)-1-(1H-1,2,4-triazol-5-yl)ethyl]-4-[1-[6-(trifluoromethyl)pyridin-3-yl]cyclopropyl]-1H-pyrrole-2-carboxamide
synonym: compound 79
approved: f
ligand name: DSM705
type: SyntheticOrganicLigand

2-TEDC
canonical SMILES: N#C/C(=C/c1ccc(c(c1)O)O)/C(=O)OCCc1cccs1
isomeric SMILES: N#C/C(=C/c1ccc(c(c1)O)O)/C(=O)OCCc1cccs1
in ch i key: KCGLTUBCAGZLHP-XYOKQWHBSA-N
in ch i: InChI=1S/C16H13NO4S/c17-10-12(8-11-3-4-14(18)15(19)9-11)16(20)21-6-5-13-2-1-7-22-13/h1-4,7-9,18-19H,5-6H2/b12-8+
comment: 2-TEDC is used as 5-, 12- and 15-lipoxygenase inhibitor <Reference id=41350/>.
iupac name: 2-thiophen-2-ylethyl (E)-2-cyano-3-(3,4-dihydroxyphenyl)prop-2-enoate
xref: CHEMBL37081
synonym: compound 24 [PMID: 2016727]
approved: f
ligand name: 2-TEDC
type: SyntheticOrganicLigand

compound 3j [PMID: 33975947]
in ch i key: VFMMJZMQRGSBSO-HFBAOOFYSA-N
in ch i: InChI=1S/C18H33BN4O6/c1-10(2)15(17(26)20-9-14(25)21-11(3)19(28)29)23-18(27)16(22-12(4)24)13-7-5-6-8-13/h10-11,13,15-16,28-29H,5-9H2,1-4H3,(H,20,26)(H,21,25)(H,22,24)(H,23,27)/t11-,15-,16-/m1/s1
comment: compound 3j is the lead compound from a series of peptidic boronic acids with antimalarial activity <Reference id=42161/>.
iupac name: [(1S)-1-[[2-[[(2R)-2-[[(2R)-2-acetamido-2-cyclopentylacetyl]amino]-3-methylbutanoyl]amino]acetyl]amino]ethyl]boronic acid
approved: f
ligand name: compound 3j [PMID: 33975947]
type: SyntheticOrganicLigand

venglustat
in ch i key: YFHRCLAKZBDRHN-MRXNPFEDSA-N
in ch i: InChI=1S/C20H24FN3O2S/c1-20(2,17-12-27-18(22-17)14-3-5-15(21)6-4-14)23-19(25)26-16-11-24-9-7-13(16)8-10-24/h3-6,12-13,16H,7-11H2,1-2H3,(H,23,25)/t16-/m1/s1
comment: Venglustat is a clinical stage oral glucosylceramide synthase (GCS) inhibitor. GCS is encoded by the UGCG gene. It was developed for potential to treat diseases in which the glycolipid glucosylceramide accumulates and leads to lysosomal dysfunction and organ damage <Reference id=42142/><Reference id=42143/>. Venglustat inhibits glucosylceramide synthesis. Its chemical structure is claimed in Genzyme's patent WO2012129084A2 <Reference id=42146/>. It has subsequently been reported to act as a substrate-competitive inhibitor of N-terminal Xaa-Pro-Lys N-methyltransferase 1 (NTMT1; Q9BV86; IC50 420 nM) <Reference id=44108/>. The venglustat analogue GENZ-667161 and the <Ligand id=7536/> analogue GENZ-123346 have been shown to inhibit replication of SARS-CoV-2 in vitro <Reference id=42145/>, potentially by disrupting the host cell membrane dynamics which the virions depend upon for infection.
iupac name: [(3S)-1-azabicyclo[2.2.2]octan-3-yl] N-[2-[2-(4-fluorophenyl)-1,3-thiazol-4-yl]propan-2-yl]carbamate
xref: CHEMBL4297611
synonym: ibiglustat
synonym: Genz-682452
synonym: SAR402671
synonym: GZ/SAR402671
approved: f
ligand name: venglustat
type: SyntheticOrganicLigand

vonoprazan
in ch i key: BFDBKMOZYNOTPK-UHFFFAOYSA-N
in ch i: InChI=1S/C17H16FN3O2S/c1-19-10-13-9-17(15-6-2-3-7-16(15)18)21(12-13)24(22,23)14-5-4-8-20-11-14/h2-9,11-12,19H,10H2,1H3
comment: Vonoprazan (TAK-438) is a first-in-class, potassium competitive acid blocker (P-CAB) class agent <Reference id=43654/><Reference id=43655/>. It reduces gastric acid production via reversible inhibition of the gastric proton pump ATPase (a.k.a. gastric H+,K+-ATPase) <Reference id=42147/><Reference id=42133/><Reference id=43655/>. The compound appears to dock within the luminal vestibule of the proton pump's alpha subunit (ATP4A) and prevents K+ access to the ion binding domain, with a Ki of 3 nM for the wild type H+,K+-ATPase <Reference id=43655/>. Vonoprazan has a faster onset of action than widely used proton pump inhibitors (PPI), doesn't require acid-mediated activation and provides long-lasting inhibition (due to its slow dissociation rate) of the gastric H+,K+-ATPase <Reference id=43652/><Reference id=43653/>.
iupac name: 1-[5-(2-fluorophenyl)-1-pyridin-3-ylsulfonylpyrrol-3-yl]-N-methylmethanamine
xref: CHEMBL2079130
synonym: TAK-438
synonym: TAK438
synonym: Vocinti®
synonym: TAKECAB®
synonym: compound 13e [PMID: 22512618]
synonym: Voquezna&reg
synonym: Takecab®
approved: t
ligand name: vonoprazan
type: SyntheticOrganicLigand

compound 4-3 [PMID: 34027661]
in ch i key: DJUQPBPAHPCBBX-UHFFFAOYSA-N
in ch i: InChI=1S/C18H14FNO2S/c1-2-17(21)20-14-5-3-4-6-15(14)23-16(11-18(20)22)12-7-9-13(19)10-8-12/h2-10,16H,1,11H2
comment: Compound 4-3 is an irreversible (covalent) benzothiazepinone type glycogen synthase kinase 3β inhibitor <Reference id=42124/>. It has favourable drug-like properties and low cytotoxicity. Compound 4-3 binds predominantly to GSK-3β's Cys14 residue, which is unique to GSK-3β and confers selectivity for this isoform over GSK-3α.
iupac name: 5-Acryloyl-2,3-dihydro-2-(4-fluorophenyl)-1,5-benzothiazepin-4(5H)-one
approved: f
ligand name: compound 4-3 [PMID: 34027661]
type: SyntheticOrganicLigand

icenticaftor
in ch i key: USHQRIKZLHNPQR-JTQLQIEISA-N
in ch i: InChI=1S/C12H13F6N3O3/c1-10(23,12(16,17)18)4-20-8(22)7-6(19)3-5(11(13,14)15)9(21-7)24-2/h3,23H,4,19H2,1-2H3,(H,20,22)/t10-/m0/s1
comment: Icenticaftor (QBW251) is a compound that potentiates/improves transport of chloride ions via mutant cystic fibrosis transmembrane conductance regulator (CFTR) ion channels <Reference id=42122/>. It is a clinical lead for cystic fibrosis and chronic obstructive pulmonary disease (COPD) <Reference id=42121/>, having demonstrated clinical proofs of concept in both conditions. In patients with CF it induced significant clinical benefit in those with Class III and IV CFTR mutations. Class III and IV mutations are those which impair gating or conductance of the channel respectively <Reference id=42123/>. The potentiator <Ligand id=4342/> is aleady approved to restore function in channels with class III mutations, but at the time of writing (May 2021) there was no approved potentiator for class IV mutant channels.
iupac name: 3-amino-6-methoxy-N-[(2S)-3,3,3-trifluoro-2-hydroxy-2-methylpropyl]-5-(trifluoromethyl)pyridine-2-carboxamide
synonym: QBW251
synonym: QBW-251
synonym: compound 33 [PMID: 34028270]
approved: f
ligand name: icenticaftor
type: SyntheticOrganicLigand

belvarafenib
in ch i key: KVCQTKNUUQOELD-UHFFFAOYSA-N
comment: Belvarafenib is a clinical stage, oral RAF kinase inhibitor that is being developed in a collaboration between Genentech and Hanmi Pharmaceuticals. The chemical structure is one of those claimed in Hanmi patent WO2013100632A1 <Reference id=42111/>.
iupac name: 4-amino-N-[1-(3-chloro-2-fluoroanilino)-6-methylisoquinolin-5-yl]thieno[3,2-d]pyrimidine-7-carboxamide
xref: CHEMBL3977543
synonym: GDC-5573
synonym: HM95573
synonym: RG6185
synonym: Example 116 [WO2013100632A1]
approved: f
ligand name: belvarafenib
type: SyntheticOrganicLigand

compound 19 [PMID: 33979649]
in ch i key: ZGUISYSWQQIAHK-JOCHJYFZSA-N
in ch i: InChI=1S/C31H38FN5O2/c1-22(28-9-5-7-24-6-3-4-8-29(24)28)36-12-10-25(11-13-36)30(38)33-21-23-18-26(32)20-27(19-23)34-31(39)37-16-14-35(2)15-17-37/h3-9,18-20,22,25H,10-17,21H2,1-2H3,(H,33,38)(H,34,39)/t22-/m1/s1
comment: This compound was reported as an inhibitor of the papain-like protease (PL-pro) of SARS-CoV-2 <Reference id=42109/>.
iupac name: N-{3-fluoro-5-[({1-[(1R)-1-(naphthalen-1-yl)ethyl]piperidin-4-yl}formamido)methyl]phenyl}-4-methylpiperazine-1-carboxamide
approved: f
ligand name: compound 19 [PMID: 33979649]
type: SyntheticOrganicLigand

SR-1114
in ch i key: WPVVPCVQEBQVLL-UHFFFAOYSA-N
in ch i: InChI=1S/C39H42N8O11S/c48-33-13-11-30(37(51)44-33)47-38(52)28-8-3-9-31(35(28)39(47)53)58-23-34(49)40-14-16-56-18-19-57-17-15-41-59(54,55)45-27-7-1-4-24(20-27)29-22-46-21-25(10-12-32(46)43-29)36(50)42-26-5-2-6-26/h1,3-4,7-10,12,20-22,26,30,41,45H,2,5-6,11,13-19,23H2,(H,40,49)(H,42,50)(H,44,48,51)
comment: SR-1114 is an ENL PROTAC degrader that was developed as part of the same study into ENL as an AML therapeutic target as the small molecule inhibitor <Ligand id=11541/> <Reference id=42107/>. Both SR-1114 and SR-0813 disrupt the transcriptional function of ENL. SR-1114 achieves this by directing ENL for cereblon-dependent degradation. SR-1114-induced ENL degradation is rapid, but reversible upon withdrawl of SR-1114, and leads to suppression of multiple ENL target genes (e.g. HOXA10, MYC, MYB, FLT3, ZEB2, and SATB1).
synonym: compound 4 [Garnar-Wortzel et al., 2021]
approved: f
ligand name: SR-1114
type: SyntheticOrganicLigand

SR-0813
in ch i key: GPMTWAPXRJMXCC-UHFFFAOYSA-N
in ch i: InChI=1S/C25H32N6O3S/c32-25(27-21-7-5-8-21)20-10-11-24-28-23(18-31(24)17-20)19-6-4-9-22(16-19)29-35(33,34)26-12-15-30-13-2-1-3-14-30/h4,6,9-11,16-18,21,26,29H,1-3,5,7-8,12-15H2,(H,27,32)
comment: SR-0813 is a small molecule inhibitor of the transcriptional coactivator ENL's interaction with other proteins <Reference id=42107/>. It targets the YEATS domain of ENL (MLLT1) and AF9 (MLLT3). The chemical structure was claimed in patent WO2021021904 <Reference id=42108/>.
iupac name: N-cyclobutyl-2-[3-(2-piperidin-1-ylethylsulfamoylamino)phenyl]imidazo[1,2-a]pyridine-6-carboxamide
synonym: compound 10 [Garnar-Wortzel et al., 2021
synonym: SR0813
approved: f
ligand name: SR-0813
type: SyntheticOrganicLigand

sulfopin
canonical SMILES: ClCC(=O)N(C1CCS(=O)(=O)C1)CC(C)(C)C
isomeric SMILES: ClCC(=O)N(C1CCS(=O)(=O)C1)CC(C)(C)C
in ch i key: NMHVAHHYKGXBMY-UHFFFAOYSA-N
in ch i: InChI=1S/C11H20ClNO3S/c1-11(2,3)8-13(10(14)6-12)9-4-5-17(15,16)7-9/h9H,4-8H2,1-3H3
comment: Sulfopin has been reported as a covalent inhibitor of peptidylprolyl cis/trans isomerase, NIMA-interacting 1 (Pin1) <Reference id=42105/>, an enzyme that is a cancer drug target. The compound interacts with Cys113 in Pin1's catalytic domain.
iupac name: 2-chloro-N-(2,2-dimethylpropyl)-N-(1,1-dioxothiolan-3-yl)acetamide
approved: f
ligand name: sulfopin
type: SyntheticOrganicLigand

SBC-115,337
in ch i key: ALQIZRCPSILFNQ-UHFFFAOYSA-N
in ch i: InChI=1S/C29H19N3O4/c33-27(30-21-15-11-19(12-16-21)29-32-23-6-2-4-8-25(23)36-29)18-9-13-22(14-10-18)31-28(34)26-17-20-5-1-3-7-24(20)35-26/h1-17H,(H,30,33)(H,31,34)
comment: SBC-115,337 is an orally bioavailable small molecule from Shifa Biomedical's patent WO2017222953A, in which it is claimed as an inhbitor of the proprotein convertase subtilisin kexin type 9 (PCSK9)/low density lipoprotein receptor (LDLR) protein-protein interaction as a novel mechanism to control dyslipidemia <Reference id=42103/><Reference id=42104/>. This compound offers a first-in-class oral lead for hypercholesterolema and more generally cardiovascular disease. In the absence of formal name-to-structure disclosure, we can speculate that SBC-115,337 may be P-21 as discussed in Shifa's press release of May 2021 (link here), based on SBC-115,337 being taken into in vivo testing. Shifa are partnering with Xontogeny to progress P-21 to clinical trial.
iupac name: N-[4-[[4-(1,3-benzoxazol-2-yl)phenyl]carbamoyl]phenyl]-1-benzofuran-2-carboxamide
xref: CHEMBL4458097
synonym: SBC-115337
approved: f
ligand name: SBC-115,337
type: SyntheticOrganicLigand

opiorphin
in ch i key: TWWFCOBVAKAKIT-SXYSDOLCSA-N
in ch i: InChI=1S/C29H48N12O8/c30-17(10-11-22(31)43)23(44)38-18(8-4-12-36-28(32)33)24(45)40-20(14-16-6-2-1-3-7-16)25(46)41-21(15-42)26(47)39-19(27(48)49)9-5-13-37-29(34)35/h1-3,6-7,17-21,42H,4-5,8-15,30H2,(H2,31,43)(H,38,44)(H,39,47)(H,40,45)(H,41,46)(H,48,49)(H4,32,33,36)(H4,34,35,37)/t17-,18-,19-,20-,21-/m0/s1
comment: Opiorphin is an endogenous pentapeptide. It reduces the breakdown of the natural analgesic enkephalins by acting as an inhibitor of enkephalin-degrading proteases including neutral ecto-endopeptidase (MME; neprilysin), ecto-aminopeptidase N (ANPEP; ANP) <Reference id=42102/> and dipeptidyl peptidase DPP3.
xref: CHEMBL2022225
synonym: Gln-Arg-Phe-Ser-Arg
synonym: L-Glutaminyl-L-arginyl-L-phenylalanyl-L-seryl-L-arginine
synonym: QRFSR peptide
approved: f
ligand name: opiorphin
type: PeptideLigand

NTP42
in ch i key: RIIKDGPBTPECSW-UHFFFAOYSA-N
comment: NTP42 is a thromboxane receptor antagonist <Reference id=42096/><Reference id=42094/>. Its chemical structure is claimed in patent WO2016203314A1 <Reference id=42097/>. TP signalling has demonstrable importance in the development and progression of pulmonary arterial hypertension (PAH). ATXA Therapeutics are progressing NTP42 into early stage clinical evaluation.
synonym: NTP-42
approved: f
ligand name: NTP42
type: SyntheticOrganicLigand

ONO-8130
in ch i key: IOXMDBQCUCDLAF-UHFFFAOYSA-N
in ch i: InChI=1S/C25H28N2O5S2/c1-16(2)13-27(34(30,31)25-26-17(3)15-33-25)22-11-20-5-4-6-21(20)12-23(22)32-14-18-7-9-19(10-8-18)24(28)29/h7-12,15-16H,4-6,13-14H2,1-3H3,(H,28,29)
comment: ONO-8130 is an EP1 receptor antagonist <Reference id=42071/>.
iupac name: 4-[[6-[2-methylpropyl-[(4-methyl-1,3-thiazol-2-yl)sulfonyl]amino]-2,3-dihydro-1H-inden-5-yl]oxymethyl]benzoic acid
xref: CHEMBL3939289
approved: f
ligand name: ONO-8130
type: SyntheticOrganicLigand

pregnanolone sulphate
in ch i key: MENQCIVHHONJLU-YZRLXODZSA-N
in ch i: InChI=1S/C21H34O5S/c1-13(22)17-6-7-18-16-5-4-14-12-15(26-27(23,24)25)8-10-20(14,2)19(16)9-11-21(17,18)3/h14-19H,4-12H2,1-3H3,(H,23,24,25)/t14-,15-,16+,17-,18+,19+,20+,21-/m1/s1
comment: Pregnanolone sulphate is an endogenous neurosteroid. It behaves as a negative allosteric modulator of NMDA-induced currents in vitro <Reference id=42066/><Reference id=42067/>. The nonsulphated analogue does not produce any significant effect on the NMDA response.
iupac name: [(3R,5R,8R,9S,10S,13S,14S,17S)-17-acetyl-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl] hydrogen sulfate
xref: CHEMBL1179566
synonym: 3 alpha-hydroxy-5 beta-pregnan-20-one sulfate
synonym: 3α-hydroxy-5β-pregnan-20-one sulfate
approved: f
ligand name: pregnanolone sulphate
type: MetaboliteLigand

eltanolone
in ch i key: AURFZBICLPNKBZ-YZRLXODZSA-N
in ch i: InChI=1S/C21H34O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h14-19,23H,4-12H2,1-3H3/t14-,15-,16+,17-,18+,19+,20+,21-/m1/s1
comment: Eltanolone (pregnanolone) is an endogenous neurosteroid that is derived from progesterone. It is a stereoisomer of <Ligand id=4108/> (allopregnanolone). Like allopregnanolone it behaves as a positive allosteric modulator of GABAA receptors. It is often formulated as the sulphate salt. Eltanolone induces sedative, anxiolytic, anesthetic, and anticonvulsant effects.
iupac name: 1-[(3R,5R,8R,9S,10S,13S,14S,17S)-3-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]ethanone
synonym: pregnanolone
synonym: Pregnan-3alpha-ol-20-one
synonym: 3α-hydroxy-5β-pregnan-20-one
synonym: 3α,5β-tetrahydroprogesterone
synonym: 3α,5β-THP
approved: f
ligand name: eltanolone
type: MetaboliteLigand

MM3122
in ch i key: ZEPMYXYJCBQSLH-VABKMULXSA-N
in ch i: InChI=1S/C31H39N9O6S/c1-18(41)36-17-26(43)37-22(13-14-25(32)42)28(45)39-23(16-19-8-3-2-4-9-19)29(46)38-21(11-7-15-35-31(33)34)27(44)30-40-20-10-5-6-12-24(20)47-30/h2-6,8-10,12,21-23H,7,11,13-17H2,1H3,(H2,32,42)(H,36,41)(H,37,43)(H,38,46)(H,39,45)(H4,33,34,35)/t21-,22-,23-/m0/s1
comment: MM3122 is aTMPRSS2 inhibitor belonging to a novel chemotype <Reference id=42064/> (this reference is a bioRxiv preprint). It inhibits entry of SARS-CoV-2 and MERS-CoV in vitro.
iupac name: (2S)-N-[(1S)-1-{[(2S)-1-(1,3-benzothiazol-2-yl)-5-carbamimidamido-1-oxopentan-2-yl]carbamoyl}-2-phenylethyl]-2-(2-acetamidoacetamido)pentanediamide
synonym: compound 4 [Mahoney et al, 2021]
synonym: MM-3122
synonym: Ac-GQFR-kbt
approved: f
ligand name: MM3122
type: SyntheticOrganicLigand

SCO-267
in ch i key: VVRXREQIOCYUKN-PMERELPUSA-N
in ch i: InChI=1S/C36H46N4O5/c1-24-7-6-8-32(38-24)40(23-36(2,3)4)35(43)29-12-11-28(44-5)20-31(29)39-17-14-25(15-18-39)22-45-33-19-27(13-16-37-33)30(21-34(41)42)26-9-10-26/h6-8,11-13,16,19-20,25-26,30H,9-10,14-15,17-18,21-23H2,1-5H3,(H,41,42)/t30-/m0/s1
comment: SCO-267 is a GPR40 full agonist <Reference id=42063/>. Agonist activation of GPR40 (which stimulates secretion of insulin and incretin) is considered to be an attractive mechanism for promoting glycemic control in the treatment of type 2 diabetes mellitus.
iupac name: (3S)-3-cyclopropyl-3-[2-[[1-[2-[2,2-dimethylpropyl-(6-methylpyridin-2-yl)carbamoyl]-5-methoxyphenyl]piperidin-4-yl]methoxy]pyridin-4-yl]propanoic acid
synonym: SCO267
approved: f
ligand name: SCO-267
type: SyntheticOrganicLigand

STM2457
in ch i key: OBERVORNENYOLE-UHFFFAOYSA-N
in ch i: InChI=1S/C25H28N6O2/c32-24-12-21(29-23-8-4-5-11-31(23)24)25(33)27-15-20-17-30-16-19(9-10-22(30)28-20)14-26-13-18-6-2-1-3-7-18/h4-5,8-12,16-18,26H,1-3,6-7,13-15H2,(H,27,33)
comment: STM2457 is a small molecule inhibitor of the methyltransferase activity of METTL3 <Reference id=42015/>. X-ray crystallography shows that STM2457 binds to the S-adenosyl methionine (SAM) binding site within the enzyme's catalytic domain. In vivo work provides evidence that METTL3 inhibition is a potential therapeutic strategy against cancers, including AML.
synonym: STM-2457
approved: f
ligand name: STM2457
type: SyntheticOrganicLigand

INCB086550
in ch i key: QARLNMDDSQMINK-BVRKHOPBSA-N
in ch i: InChI=1S/C41H39N7O4/c1-24-32(5-3-7-34(24)40-46-36-17-26(15-30(18-42)38(36)52-40)20-47-13-10-29(22-47)41(50)51)33-6-4-8-35(25(33)2)45-39-37-28(9-12-43-39)16-27(19-44-37)21-48-14-11-31(49)23-48/h3-9,12,15-17,19,29,31,49H,10-11,13-14,20-23H2,1-2H3,(H,43,45)(H,50,51)/t29-,31-/m1/s1
comment: INCB086550 is a small molecule PD-L1 inhibitor. This is the structure that was disclosed during the ACS First Disclosures session at the spring 2021 meeting. There are many potential stereo versions of this molecule, so we await formal peer-reviewed name to structure disclosure to confirm the structure. INCB086550 was designed by Incyte Corporation for activity against advanced solid tumours, as an alternative to anti-PD-L1 monoclonal antibodies. This isomer is calimed as example 24 in patent WO2018119266A1 <Reference id=42008/>.
iupac name: (3R)-1-[[7-cyano-2-[3-[3-[[3-[[(3R)-3-hydroxypyrrolidin-1-yl]methyl]-1,7-naphthyridin-8-yl]amino]-2-methylphenyl]-2-methylphenyl]-1,3-benzoxazol-5-yl]methyl]pyrrolidine-3-carboxylic acid
approved: f
ligand name: INCB086550
type: SyntheticOrganicLigand

[3H]-TCS 1102
in ch i key: YSBGRVXJEMSEQY-DEOSSOPVSA-N
in ch i: InChI=1S/C27H26N4O2S/c1-30-23-15-8-7-14-22(23)29-27(30)34-18-25(32)31-17-9-16-24(31)26(33)28-21-13-6-5-12-20(21)19-10-3-2-4-11-19/h2-8,10-15,24H,9,16-18H2,1H3,(H,28,33)/t24-/m0/s1
comment: This is the radio-labelled version of the dual orexin antagonist <Ligand id=9304/> <Reference id=31588/>. We do not know the location of the tritium isotope.
synonym: [3H]-BBAC
synonym: [3H]-compound 18
approved: f
ligand name: [3H]-TCS 1102
type: SyntheticOrganicLigand

AZD5305
in ch i key: WQAVGRAETZEADU-UHFFFAOYSA-N
in ch i: InChI=1S/C22H26N6O2/c1-3-16-11-19-20(26-21(16)29)10-15(12-24-19)14-27-6-8-28(9-7-27)17-4-5-18(25-13-17)22(30)23-2/h4-5,10-13H,3,6-9,14H2,1-2H3,(H,23,30)(H,26,29)
comment: AZD5305 is a novel PARP1-selective inhibitor that was developed as an oncology therapeutic <Reference id=42007/>.
synonym: AZD-5305
synonym: example 4 [WO2021013735]
approved: f
ligand name: AZD5305
type: SyntheticOrganicLigand

PF-07104091
in ch i key: MTNBRBDFNSGQKB-GXTWGEPZSA-N
in ch i: InChI=1S/C19H28N6O4/c1-11(2)20-19(27)29-14-6-5-12(7-14)15-9-17(23-22-15)21-18(26)16-8-13(10-28-4)24-25(16)3/h8-9,11-12,14H,5-7,10H2,1-4H3,(H,20,27)(H2,21,22,23,26)/t12-,14+/m0/s1
comment: PF-07104091 is a novel, selective CDK2 inhibitor. It is identical to the chemical structure for example 13 that is claimed in patent WO2020157652 <Reference id=42006/>. We await formal peer reviewed name to structure disclosure to confirm the structure of PF-07104091.
synonym: example 13 [WO2020157652]
synonym: PF07104091
approved: f
ligand name: PF-07104091
type: SyntheticOrganicLigand

aficamten
in ch i key: IOVAZWDIRCRMTM-OAHLLOKOSA-N
in ch i: InChI=1S/C18H19N5O2/c1-3-16-21-17(22-25-16)12-4-6-14-11(8-12)5-7-15(14)20-18(24)13-9-19-23(2)10-13/h4,6,8-10,15H,3,5,7H2,1-2H3,(H,20,24)/t15-/m1/s1
comment: Aficamten (CK-3773274) is an orally administered cardiac myosin inhibitor that was developed by Cytokinetics as a potential treatment for hypertrophic cardiomyopathies <Reference id=43025/><Reference id=42004/><Reference id=42005/>. It was designed to reduce the hypercontractility of cardiac sarcomeres that is thought to drive hypertrophy and fibrosis in heart muscle, by binding directly to a distinct and selective allosteric binding site on cardiac myosin.
iupac name: N-[(1R)-5-(5-ethyl-1,2,4-oxadiazol-3-yl)-2,3-dihydro-1H-inden-1-yl]-1-methylpyrazole-4-carboxamide
synonym: CK-3773274
synonym: CK3773274
synonym: CK-274
approved: f
ligand name: aficamten
type: SyntheticOrganicLigand

pociredir
in ch i key: JQBUTSBIFNKJMW-CYBMUJFWSA-N
in ch i: InChI=1S/C22H18FN5O2/c1-12-14(3-2-6-24-12)15-7-19-22(28-11-26-27-21(15)28)25-8-16-17(23)4-5-18-20(16)13(9-29-18)10-30-19/h2-7,11,13,25H,8-10H2,1H3/t13-/m1/s1
comment: FTX-6058 binds to embryonic ectoderm development (EED) and induces foetal haemoglobin (HbF) tetramer production via modulation of PRC2. It was developed by Fulcrum Therapeutics as an oral drug for the treatment of sickle cell disease or beta thalassemia. We matched the chemical structure for the INN 'pociredir' (from the WHO's proposed INN list 127, July 2022) to the structure for FTX-6058.
synonym: Example 90 [WO2020190754]
synonym: FTX6058
synonym: FTX-6058
approved: f
ligand name: pociredir
type: SyntheticOrganicLigand

(2S)-2-[(6Z,15Z)-20-hydroxyicosa-6,15-dienamido]butanedioate
canonical SMILES: OCCCC/C=C/CCCCCCC/C=C/CCCCC(=O)N[C@H](C(=O)[O-])CC(=O)[O-]
isomeric SMILES: OCCCC/C=C/CCCCCCC/C=C/CCCCC(=O)N[C@H](C(=O)[O-])CC(=O)[O-]
in ch i key: YOJFRYNVBRTSNN-WYCJAXOMSA-L
comment: Antagonises the vascular prohypertensive actions of 20-hydroxyeicosatetraenoic acid (<Ligand id=4103/>) <Reference id=42002/>. We show the parent structure without the two sodium atoms.
iupac name: (2S)-2-[(6Z,15Z)-20-hydroxyicosa-6,15-dienamido]butanedioate
synonym: 20-HETE receptor antagonist (AAA)
approved: f
ligand name: (2S)-2-[(6Z,15Z)-20-hydroxyicosa-6,15-dienamido]butanedioate
type: SyntheticOrganicLigand

compound 17 [PMID: 33655614]
in ch i key: WGTDTRRECQYDFW-UHFFFAOYSA-N
in ch i: InChI=1S/C14H8Cl2N2O2/c15-9-1-2-12-8(3-9)4-13(18-12)14(19)20-11-5-10(16)6-17-7-11/h1-7,18H
comment: Compound 17 is a SARS‐CoV‐2 Mpro inhibitor <Reference id=41990/>.
approved: f
ligand name: compound 17 [PMID: 33655614]
type: SyntheticOrganicLigand

saccharin
canonical SMILES: O=C1NS(=O)(=O)c2c1cccc2
isomeric SMILES: O=C1NS(=O)(=O)c2c1cccc2
in ch i key: CVHZOJJKTDOEJC-UHFFFAOYSA-N
in ch i: InChI=1S/C7H5NO3S/c9-7-5-3-1-2-4-6(5)12(10,11)8-7/h1-4H,(H,8,9)
iupac name: 2,3-dihydro-1$l^{6},2-benzothiazole-1,1,3-trione
xref: CHEMBL310671
synonym: benzosulfimide
synonym: saccharimide
approved: f
ligand name: saccharin
type: SyntheticOrganicLigand

compound 12d [PMID: 33821636]
in ch i key: KSQVGVMZECCPAT-AEFFLSMTSA-N
in ch i: InChI=1S/C20H27BN4O4/c1-2-7-16(24-20(27)17-14-22-12-13-23-17)19(26)25-18(21(28)29)11-6-10-15-8-4-3-5-9-15/h3-5,8-9,12-14,16,18,28-29H,2,6-7,10-11H2,1H3,(H,24,27)(H,25,26)/t16-,18+/m1/s1
comment: Compound 12d is a boronic acid-containing agent that was designed as a selective inhibitor of the AAA+ ATPase, LONP1 <Reference id=41956/>. It provides a tool compound that is suitable for investigating LONP1 biology in vitro. Compound 12d has negligible activity at the 20S proteasome.
iupac name: ((R)-4-Phenyl-1-((R)-2-(pyrazine-2-carboxamido)pentanamido)butyl)boronic acid
approved: f
ligand name: compound 12d [PMID: 33821636]
type: SyntheticOrganicLigand

compound 8 [PMID: 33655614]
in ch i key: JGNSKMJHNUAKGY-OHSXHVKISA-N
in ch i: InChI=1S/C32H43N7O6/c1-6-24(36-31(44)45-20-23-15-11-8-12-16-23)28(41)37-27(32(2,3)4)29(42)35-25(19-22-13-9-7-10-14-22)30(43)38(5)39(21-33)18-17-26(34)40/h7-16,24-25,27H,6,17-20H2,1-5H3,(H2,34,40)(H,35,42)(H,36,44)(H,37,41)/t24-,25-,27+/m0/s1
comment: Compound 8 is a SARS‐CoV‐2 Mpro inhibitor <Reference id=41990/>.
iupac name: benzyl N-[(1S)-1-{[(1S)-1-{[(1S)-1-[N'-(2-carbamoylethyl)-N'-cyano-N-methylhydrazinecarbonyl]-2-phenylethyl]carbamoyl}-2,2-dimethylpropyl]carbamoyl}propyl]carbamate
approved: f
ligand name: compound 8 [PMID: 33655614]
type: SyntheticOrganicLigand

soticlestat
in ch i key: XKUZMIUSBMCVPP-UHFFFAOYSA-N
in ch i: InChI=1S/C23H23N3O2/c27-22(20-7-4-12-25-21(20)19-8-13-24-14-9-19)26-15-10-23(28,11-16-26)17-18-5-2-1-3-6-18/h1-9,12-14,28H,10-11,15-17H2
comment: Soticlestat (TAK-935, previously OV935) is a first-in-class, clinical stage, orally administered cholesterol 24-hydroxylase (CYP46A1) inhibitor. It is being investigated as a novel anti-epileptic modality for pediatric forms of epilepsy <Reference id=41980/>, such as Dravet syndrome <Reference id=41981/><Reference id=41982/> and Lennox-Gastaut syndrome <Reference id=41983/>. Cholesterol 24-hydroxylase is a brain-specific enzyme (in humans) that converts cholesterol to 24S-hydroxycholesterol. 24S-hydroxycholesterol acts as a positive allosteric modulator of N-methyl-D-aspartate (NMDA) receptors. Soticlestat blocks 24S-hydroxycholesterol production in the brain in an in vivo mouse model <Reference id=41984/>.
iupac name: (4-benzyl-4-hydroxypiperidin-1-yl)-(2-pyridin-4-ylpyridin-3-yl)methanone
xref: CHEMBL4298172
synonym: TAK-935
synonym: OV935
approved: f
ligand name: soticlestat
type: SyntheticOrganicLigand

TAK-418
in ch i key: QZNGFWQWWSECMG-HUUCEWRRSA-N
in ch i: InChI=1S/C17H24N2O2S/c20-17(19-13-3-5-21-6-4-13)12-7-16(22-10-12)14-8-15(14)18-9-11-1-2-11/h7,10-11,13-15,18H,1-6,8-9H2,(H,19,20)/t14-,15-/m1/s1
comment: TAK-418 is an orally administered, brain-penetrant lysine-specific demethylase 1 (LSD1; KDM1A) inhbitor that was developed by Takeda for potential to treat neurodevelopmental disorders <Reference id=41977/><Reference id=41978/>. The compound is proposed to correct the persistent epigenetic dysregulation (thus restoring gene expression homeostasis) that is believed to underlie the pathophysiology of neurodevelopmental disorders such as autism spectrum disorder.
iupac name: 5-[(1R,2R)-2-(cyclopropylmethylamino)cyclopropyl]-N-(oxan-4-yl)thiophene-3-carboxamide
xref: CHEMBL3775474
approved: f
ligand name: TAK-418
type: SyntheticOrganicLigand

K777
in ch i key: VZSXPUDQSLKVIR-JDXGNMNLSA-N
in ch i: InChI=1S/C32H40N4O4S/c1-35-20-22-36(23-21-35)32(38)34-30(25-27-13-7-3-8-14-27)31(37)33-28(18-17-26-11-5-2-6-12-26)19-24-41(39,40)29-15-9-4-10-16-29/h2-16,28,30H,17-25H2,1H3,(H,33,37)(H,34,38)/t28-,30-/m0/s1
comment: K777 is a clinical stage irreversible cysteine protease inhibitor. It has reported activity at human cathepsin L and other CA clade cysteine proteases <Reference id=41971/><Reference id=41972/><Reference id=41973/><Reference id=41974/>. Original reports revealed anti-parasitic effects in vitro and in animal models <Reference id=41974/><Reference id=41975/><Reference id=41976/>. SARS-CoV-2: Cathepsin L in human host cells is implicated in the processing (cleavage) of the viral spike protein of SARS coronaviruses, that is part of the viral entry process. K777 blocks SARS-CoV-2 infection in vitro.
iupac name: N-[(2S)-1-[[(3S)-1-(benzenesulfonyl)-5-phenylpentan-3-yl]amino]-1-oxo-3-phenylpropan-2-yl]-4-methylpiperazine-1-carboxamide
synonym: K11777
synonym: S-001
synonym: SLV213
synonym: K-777
approved: f
ligand name: K777
type: SyntheticOrganicLigand

CVN424
in ch i key: HSWVJQBEXRKOBZ-QGZVFWFLSA-N
in ch i: InChI=1S/C24H29F2N5O3/c1-15(32)31-10-6-20-21(13-31)28-23(27-17-7-11-33-14-17)24(29-20)30-8-4-18(5-9-30)34-22-3-2-16(25)12-19(22)26/h2-3,12,17-18H,4-11,13-14H2,1H3,(H,27,28)/t17-/m1/s1
comment: CVN424 is a first-in-class, clinical stage, nondopaminergic inverse agonist of GPR6. It is orally bioavailable, and can penetrate the CNS <Reference id=41970/><Reference id=41969/>. In in vivo Parkinson's disease models, inhibiting GPR6 activity with CVN424 normalises both activity in basal ganglia circuitry and motor behaviour.
iupac name: 1-[2-[4-(2,4-difluorophenoxy)piperidin-1-yl]-3-[[(3R)-oxolan-3-yl]amino]-7,8-dihydro-5H-pyrido[3,4-b]pyrazin-6-yl]ethanone
synonym: compound 6i [PMID: 33861086]
synonym: CVN-424
approved: f
ligand name: CVN424
type: SyntheticOrganicLigand

zavegepant
in ch i key: JJVAPHYEOZSKJZ-JGCGQSQUSA-N
in ch i: InChI=1S/C36H46N8O3/c1-24-19-25(20-28-23-37-40-33(24)28)21-32(35(46)43-17-15-42(16-18-43)29-9-11-41(2)12-10-29)39-36(47)44-13-7-26(8-14-44)30-22-27-5-3-4-6-31(27)38-34(30)45/h3-6,19-20,22-23,26,29,32H,7-18,21H2,1-2H3,(H,37,40)(H,38,45)(H,39,47)/t32-/m1/s1
comment: Zavegepant is a clinical stage oral CGRP receptor antagonist <Reference id=41966/><Reference id=41967/>, that was developed as a drug to prevent migraine. It has been designed for intranasal delivery.
iupac name: N-[(2R)-3-(7-methyl-1H-indazol-5-yl)-1-[4-(1-methylpiperidin-4-yl)piperazin-1-yl]-1-oxopropan-2-yl]-4-(2-oxo-1H-quinolin-3-yl)piperidine-1-carboxamide
xref: CHEMBL2397415
synonym: BMS742413
synonym: BHV-3500
synonym: BMS-742413
approved: f
ligand name: zavegepant
type: SyntheticOrganicLigand

ARV110
in ch i key: CLCTZVRHDOAUGJ-SYVGMNBRSA-N
comment: ARV110 is a bifunctional compound (PROTAC). One end of the molecule binds to the androgen receptor and the other binds to the cereblon E3 ligase and directs the AR for proteasome-mediated degradation <Reference id=41963/>. It has clinical potential as an oral therapy for metastatic castration-resistant prostate cancer. PubChem CID 134414307 represents the molecule without specified stereo chemistry.
iupac name: 6-[4-({4-[2-(2,6-dioxopiperidin-3-yl)-6-fluoro-1,3-dioxo-2,3-dihydro-1H-isoindol-5-yl]piperazin-1-yl}methyl)piperidin-1-yl]-N-[(1r,4r)-4-(3-chloro-4-cyanophenoxy)cyclohexyl]pyridazine-3-carboxamide
synonym: ARV-110
synonym: compound 406 [WO2018071606A1]
approved: f
ligand name: ARV110
type: SyntheticOrganicLigand

ARV471
in ch i key: TZZDVPMABRWKIZ-MFTLXVFQSA-N
in ch i: InChI=1S/C45H49N5O4/c51-37-12-15-39-33(27-37)8-13-38(31-4-2-1-3-5-31)43(39)32-6-9-35(10-7-32)48-20-18-30(19-21-48)28-47-22-24-49(25-23-47)36-11-14-40-34(26-36)29-50(45(40)54)41-16-17-42(52)46-44(41)53/h1-7,9-12,14-15,26-27,30,38,41,43,51H,8,13,16-25,28-29H2,(H,46,52,53)/t38-,41?,43+/m1/s1
comment: ARV471 is a bifunctional compound that is estrogen receptor (ER) degrader (PROTAC) <Reference id=41962/>. It uses a cereblon-based binder to direct ER protein degradation. ARV471 is being investigated for potential to treat breast cancer.
iupac name: 3-[6-[4-[[1-[4-[(1R,2S)-6-hydroxy-2-phenyl-1,2,3,4-tetrahydronaphthalen-1-yl]phenyl]piperidin-4-yl]methyl]piperazin-1-yl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione
synonym: ARV-471
synonym: compound 341 [WO2018102725A1]
approved: f
ligand name: ARV471
type: SyntheticOrganicLigand

M4205
in ch i key: LVMAULGVWBINFP-UHFFFAOYSA-N
in ch i: InChI=1S/C29H32N8O/c1-35-20-24(18-34-35)23-7-5-22(6-8-23)17-30-28-16-26(32-21-33-28)27-19-31-29-15-25(9-13-37(27)29)38-14-4-12-36-10-2-3-11-36/h5-9,13,15-16,18-21H,2-4,10-12,14,17H2,1H3,(H,30,32,33)
comment: M4205 is a potent and selective inhibitor of the KIT proto-oncogene, receptor tyrosine kinase (cKIT). It retains activity against cKIT with exon 11, 13 or 17 resistance mutations, and provides good selectivity in biochemical and cellular assays. M4205's ADME profile supports its potential as a clinical candidate. Merck intend to progress M4205 to clinical evaluation for GIST (information as of April 2021).
iupac name: N-[[4-(1-methylpyrazol-4-yl)phenyl]methyl]-6-[7-(3-pyrrolidin-1-ylpropoxy)imidazo[1,2-a]pyridin-3-yl]pyrimidin-4-amine
synonym: M-4205
approved: f
ligand name: M4205
type: SyntheticOrganicLigand

BMS-986299
in ch i key: UHNRLQRZRNKOKU-UHFFFAOYSA-N
in ch i: InChI=1S/C18H19N7O/c1-3-25(10(2)26)9-15-22-16-12-5-4-11(13-6-7-20-24-13)8-14(12)21-18(19)17(16)23-15/h4-8H,3,9H2,1-2H3,(H2,19,21)(H,20,24)(H,22,23)
comment: BMS-986299 is a NLRP3 inflammasome modulator (agonist) <Reference id=41959/>. It induces production of IL-1β and IL-8 and it is being examined for immunomodulatory and antineoplastic activities. Enhanced IL-8 is predicted to induce tumouricidal activity of natural killer (NK) cells against cancer cells.
synonym: compound 112 [WO2018152396A1]
synonym: BMS986299
approved: f
ligand name: BMS-986299
type: SyntheticOrganicLigand

ML1000
in ch i key: GLLOOYDKCPXZBT-WCDFTICCSA-N
in ch i: InChI=1S/C28H45N5O6/c1-14-15(10-11-39-14)12-17(20(34)22(29)35)30-23(36)19-18-16(28(18,8)9)13-33(19)24(37)21(26(2,3)4)31-25(38)32-27(5,6)7/h15-19,21H,1,10-13H2,2-9H3,(H2,29,35)(H,30,36)(H2,31,32,38)/t15-,16-,17+,18-,19-,21+/m0/s1
comment: ML1000 is a representative of a new class (chemical scaffold) of coronavirus main protease (Mpro) inhibitors <Reference id=41957/>. Structurally it is derived from the ketoamide inhibitor <Ligand id=7876/> with a γ-lactamyl group in place of the P1 cyclobutanyl group.
iupac name: (3R)-3-{[(1R,2S,5S)-3-[(2S)-2-[(tert-butylcarbamoyl)amino]-3,3-dimethylbutanoyl]-6,6-dimethyl-3-azabicyclo[3.1.0]hexan-2-yl]formamido}-4-[(3R)-2-methylideneoxolan-3-yl]-2-oxobutanamide
approved: f
ligand name: ML1000
type: SyntheticOrganicLigand

nipecotic acid
canonical SMILES: OC(=O)C1CCCNC1
isomeric SMILES: OC(=O)C1CCCNC1
in ch i key: XJLSEXAGTJCILF-UHFFFAOYSA-N
in ch i: InChI=1S/C6H11NO2/c8-6(9)5-2-1-3-7-4-5/h5,7H,1-4H2,(H,8,9)
iupac name: piperidine-3-carboxylic acid
xref: CHEMBL277498
approved: f
ligand name: nipecotic acid
type: SyntheticOrganicLigand

65PF
canonical SMILES: O=C1CC(Oc2c1c1C=CCOc1cc2)c1ccccc1
isomeric SMILES: O=C1CC(Oc2c1c1C=CCOc1cc2)c1ccccc1
in ch i key: XIKPIBLKOKRKJQ-UHFFFAOYSA-N
in ch i: InChI=1S/C18H14O3/c19-14-11-17(12-5-2-1-3-6-12)21-16-9-8-15-13(18(14)16)7-4-10-20-15/h1-9,17H,10-11H2
comment: 65PF is a small-molecule probe that can be used to explore the active site cavity of cytochrome P450 enzyme 1A1 <Reference id=29717/>.
iupac name: 3-phenyl-1H,2H,3H,8H-pyrano[3,2-f]chromen-1-one
approved: f
ligand name: 65PF
type: SyntheticOrganicLigand

lopinavir
in ch i key: KJHKTHWMRKYKJE-SUGCFTRWSA-N
in ch i: InChI=1S/C37H48N4O5/c1-25(2)34(41-20-12-19-38-37(41)45)36(44)39-30(21-28-15-7-5-8-16-28)23-32(42)31(22-29-17-9-6-10-18-29)40-33(43)24-46-35-26(3)13-11-14-27(35)4/h5-11,13-18,25,30-32,34,42H,12,19-24H2,1-4H3,(H,38,45)(H,39,44)(H,40,43)/t30-,31-,32-,34-/m0/s1
comment: Lopinavir is an antiretroviral protease inhibitor. It has subsequently been discovered to exhibit antiviral activity against human papilloma virus (HPV), and to inhibit MERS-CoV replication in vitro <Reference id=41948/>. Antiviral activity against SARS-CoV-2 has been explored <Reference id=42058/>, however lopinavir/ritonavir therapy provided no benefit in hospitalised COVID-19 patients <Reference id=41949/>.
iupac name: (2S)-N-[(2S,4S,5S)-5-[[2-(2,6-dimethylphenoxy)acetyl]amino]-4-hydroxy-1,6-diphenylhexan-2-yl]-3-methyl-2-(2-oxo-1,3-diazinan-1-yl)butanamide
xref: CHEMBL729
synonym: ABT-378
synonym: ABT378
synonym: Kaletra® (LPV+RTV)
synonym: Aluviran®
synonym: A-157378-0
synonym: A-1573780
approved: t
ligand name: lopinavir
type: SyntheticOrganicLigand

nirmatrelvir
in ch i key: LIENCHBZNNMNKG-OJFNHCPVSA-N
in ch i: InChI=1S/C23H32F3N5O4/c1-21(2,3)16(30-20(35)23(24,25)26)19(34)31-10-13-14(22(13,4)5)15(31)18(33)29-12(9-27)8-11-6-7-28-17(11)32/h11-16H,6-8,10H2,1-5H3,(H,28,32)(H,29,33)(H,30,35)/t11-,12-,13-,14-,15-,16+/m0/s1
comment: PF-07321332 (nirmatrelvir) is an oral antiviral clinical lead. It is a covalent inhibitor of SARS-CoV-2 Mpro (main protease, 3CLpro) that binds to cysteine145 within the enzyme's catalytic domain <Reference id=43255/>. Mpro is essential for coronavirus replication. Inhibiting Mpro actvity blocks replication at an early stage in the virus' life cycle. Due to structural similarities between the Mpro's of other coronavirusus, PF-07321332 offers the potential of pan-coronavirus activity. In vitro it is suggested to inhibit replication of CoV-2 variants including delta and omicron. PF-07321332 is structurally similar to <Ligand id=11508/>. Prior to peer-reviewed name-to-structure disclosure, we obtained the structure represented here from an online report by Dr Bethany Halford who attended a session by Dafydd Owen (Pfizer) at the ACS Spring 2021 meeting (@beth_halford image on Twitter) which rendered the SMILES string N#C[C@H](C[C@@H]1CCNC1=O)NC(=O)[C@H]1N(C[C@H]2[C@@H]1C2(C)C)C(=O)[C@H](C(C)(C)C)NC(=O)C(F)(F)F. PF-07321332's chemical structure was formally disclosed in Owen et al's Science article in November 2021 <Reference id=43276/>, and this confirmed the structure that was obtained from the ACS meeting.
iupac name: (1R,2S,5S)-N-[(1S)-1-cyano-2-[(3S)-2-oxopyrrolidin-3-yl]ethyl]-3-[(2S)-3,3-dimethyl-2-(2,2,2-trifluoroacetamido)butanoyl]-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxamide
synonym: PF-07321332
synonym: PF07321332
synonym: Paxlovid® (nirmatrelvir + ritonavir)
synonym: example E61 [WO2021250648A1]
approved: t
ligand name: nirmatrelvir
type: SyntheticOrganicLigand

viloxazine
canonical SMILES: CCOc1ccccc1OCC1CNCCO1
isomeric SMILES: CCOc1ccccc1OCC1CNCCO1
in ch i key: YWPHCCPCQOJSGZ-UHFFFAOYSA-N
in ch i: InChI=1S/C13H19NO3/c1-2-15-12-5-3-4-6-13(12)17-10-11-9-14-7-8-16-11/h3-6,11,14H,2,7-10H2,1H3
comment: Viloxazine was originally described as a selective norepinephrine reuptake inhibitor (NRI), principally based on its ability to potentiate noradrenergic effects. It also modulates 5-HT (serotonin) activity, via antagonistic activity at 5-HT2B and agonistic activity at 5-HT2C receptors, and it increases extracellular 5-HT levels in the prefrontal cortex (PFC) <Reference id=41944/>. Viloxazine's chemical structure is different from conventional tri- or tetra-cyclic antidepressants. The INN stipulates a racemic mixture of enantiomers. We show the structure without specified stereochemistry to represent the mixture. The hydrocholride salt (SPN-812) was progressed by Supernus Pharmaceuticals for attention deficit hyperactivity disorder (ADHD) in children and adults.
iupac name: 2-[(2-ethoxyphenoxy)methyl]morpholine
xref: CHEMBL306700
synonym: ICI-58,834
synonym: ICI-58834
synonym: Emovit®
synonym: Qelbree®
approved: t
ligand name: viloxazine
type: SyntheticOrganicLigand

PCS1055
in ch i key: ATHZIFFSGSWIAU-UHFFFAOYSA-N
in ch i: InChI=1S/C27H32N4/c1-2-7-22(8-3-1)20-31-17-14-21(15-18-31)13-16-28-26-19-24-11-6-10-23-9-4-5-12-25(23)27(24)30-29-26/h1-5,7-9,12,19,21H,6,10-11,13-18,20H2,(H,28,29)
comment: PCS1055 is a muscarinic M4 receptor antagonist <Reference id=41877/>.
xref: CHEMBL88223
synonym: PCS-1055
approved: f
ligand name: PCS1055
type: SyntheticOrganicLigand

PD 102807
in ch i key: VDDUJINYXKGZLV-UHFFFAOYSA-N
in ch i: InChI=1S/C23H24N2O4/c1-4-28-23(26)20-13(2)24-18-7-8-19-17(21(18)20)12-25-10-9-14-11-15(27-3)5-6-16(14)22(25)29-19/h5-8,11,22,24H,4,9-10,12H2,1-3H3
iupac name: ethyl 17-methoxy-6-methyl-12-oxa-1,7-diazapentacyclo[11.8.0.03,11.04,8.014,19]henicosa-3(11),4(8),5,9,14(19),15,17-heptaene-5-carboxylate
xref: CHEMBL59898
synonym: LSM-1888
synonym: LSM1888
synonym: PD-102807
synonym: PD102807
approved: f
ligand name: PD 102807
type: SyntheticOrganicLigand

[3H]4-DAMP
canonical SMILES: O=C(C(c1ccccc1)c1ccccc1)OC1CC[N+](CC1)(C)C
isomeric SMILES: O=C(C(c1ccccc1)c1ccccc1)OC1CC[N+](CC1)(C)C
in ch i key: HYJRTXSYDAFGJK-UHFFFAOYSA-N
in ch i: InChI=1S/C21H26NO2/c1-22(2)15-13-19(14-16-22)24-21(23)20(17-9-5-3-6-10-17)18-11-7-4-8-12-18/h3-12,19-20H,13-16H2,1-2H3/q+1
approved: f
ligand name: [3H]4-DAMP
type: SyntheticOrganicLigand

S1P d20:1
canonical SMILES: CCCCCCCCCCCCCCC/C=C/[C@H]([C@H](COP(=O)(O)[O-])[NH3+])O
isomeric SMILES: CCCCCCCCCCCCCCC/C=C/[C@H]([C@H](COP(=O)(O)[O-])[NH3+])O
in ch i key: YUUWWSOTAGQJFW-YIVRLKKSSA-N
in ch i: InChI=1S/C20H42NO5P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-20(22)19(21)18-26-27(23,24)25/h16-17,19-20,22H,2-15,18,21H2,1H3,(H2,23,24,25)/b17-16+/t19-,20+/m0/s1
comment: S1P d20:1 is S1P with a 20-carbon long-chain base length <Reference id=41871/>. Mechanistically it may behave as an endogenous modulator of S1P signaling via partial agonism at the S1P2 receptor.
iupac name: [(E,2S,3R)-2-azaniumyl-3-hydroxyicos-4-enyl] hydrogen phosphate
synonym: Sphingosine-1-Phosphate (d20:1)
synonym: D-erythro-sphingosine-1-phosphate (C20 base)
synonym: S1P (d20:1)
approved: f
ligand name: S1P d20:1
type: SyntheticOrganicLigand

BMS-986104 derivative 24
in ch i key: CMZZUAAIKUIMSG-BULFRSBZSA-N
in ch i: InChI=1S/C22H35NO2/c1-25-12-4-2-3-5-17-6-7-19-14-20(9-8-18(19)13-17)21-10-11-22(23,15-21)16-24/h8-9,14,17,21,24H,2-7,10-13,15-16,23H2,1H3/t17-,21-,22+/m0/s1
comment: This is a biased agonist of the S1P1 receptor, with immunomodulatory potential <Reference id=41870/>
iupac name: [(1R,3S)-1-amino-3-[(6S)-6-(5-methoxypentyl)-5,6,7,8-tetrahydronaphthalen-2-yl]cyclopentyl]methanol
synonym: compound 24 [PMID: 33492963]
approved: f
ligand name: BMS-986104 derivative 24
type: SyntheticOrganicLigand

BMS-986104 derivative 12
in ch i key: PYZTXDCPUPYILV-TYCQWZJGSA-N
in ch i: InChI=1S/C21H33NO2/c1-2-24-11-3-4-16-5-6-18-13-19(8-7-17(18)12-16)20-9-10-21(22,14-20)15-23/h7-8,13,16,20,23H,2-6,9-12,14-15,22H2,1H3/t16-,20+,21-/m1/s1
comment: This is a biased agonist of the S1P1 receptor, with immunomodulatory potential <Reference id=41870/>
iupac name: [(1R,3S)-1-amino-3-[(6S)-6-(3-ethoxypropyl)-5,6,7,8-tetrahydronaphthalen-2-yl]cyclopentyl]methanol
synonym: compound 12 [PMID: 33492963]
approved: f
ligand name: BMS-986104 derivative 12
type: SyntheticOrganicLigand

BMS-986166
in ch i key: QCMHGCDOZLWPOT-FMNCTDSISA-N
in ch i: InChI=1S/C25H33NO2/c1-28-24-5-3-2-4-19(24)8-6-18-7-9-21-15-22(11-10-20(21)14-18)23-12-13-25(26,16-23)17-27/h2-5,10-11,15,18,23,27H,6-9,12-14,16-17,26H2,1H3/t18-,23+,25-/m1/s1
comment: BMS-986166 is a SIP1R biased agonist <Reference id=41867/>. It is proposed for immunomodulatory potential in autoimmune diseases. The active entity is the phosphate metabolite BMS-986166-P, but we show the parent molecule here.
iupac name: [(1R,3S)-1-amino-3-[(6S)-6-[2-(2-methoxyphenyl)ethyl]-5,6,7,8-tetrahydronaphthalen-2-yl]cyclopentyl]methanol
synonym: BMS986166
synonym: compound 14a [PMID: 30785748]
approved: f
ligand name: BMS-986166
type: SyntheticOrganicLigand

CPN-223
in ch i key: ZETNXOFZFFDUSA-RRXWZPBSSA-N
in ch i: InChI=1S/C59H75N15O8/c60-50(75)35-47(52(61)77)72-53(78)44(17-8-30-67-58(62)63)70-56(81)49-19-10-32-74(49)57(82)46(18-9-31-68-59(64)65)71-55(80)48(34-38-22-26-42(27-23-38)40-13-2-1-3-14-40)73-54(79)45(69-51(76)20-6-11-39-12-7-29-66-36-39)28-24-37-21-25-41-15-4-5-16-43(41)33-37/h1-5,7,12-16,21-23,25-27,29,33,36,44-49H,6,8-11,17-20,24,28,30-32,34-35H2,(H2,60,75)(H2,61,77)(H,69,76)(H,70,81)(H,71,80)(H,72,78)(H,73,79)(H4,62,63,67)(H4,64,65,68)/t44-,45-,46-,47-,48-,49-/m0/s1
comment: CPN-223 is a neuromedin U receptor 1 (NMUR1) partial agonist <Reference id=41862/>. It has been optimised for NMUR1-selectivity and serum stability.
synonym: analogue 8 [PMID: 32721452]
approved: f
ligand name: CPN-223
type: PeptideLigand

zaurategrast
in ch i key: KYHVWHYLKOHLKA-FQEVSTJZSA-N
in ch i: InChI=1S/C26H25BrN4O3/c27-21-22(26(23(21)32)10-2-1-3-11-26)31-20(25(33)34)14-16-4-6-18(7-5-16)30-24-19-15-28-12-8-17(19)9-13-29-24/h4-9,12-13,15,20,31H,1-3,10-11,14H2,(H,29,30)(H,33,34)/t20-/m0/s1
comment: Zaurategrast (CDP-323) is a small molecule inhibitor of α4-containing integrin complexes that was developed by Celltech <Reference id=41847/>. It was intended as a new oral drug treatment for multiple sclerosis <Reference id=41845/>. Zaurategrast has the same mechanism of action as the approved MS therapeutic <Ligand id=6591/>. Zaurategrast is an ester prodrug whose active entity is CT7758 <Reference id=41848/>.
iupac name: (2S)-2-[(2-bromo-3-oxospiro[3.5]non-1-en-1-yl)amino]-3-[4-(2,7-naphthyridin-1-ylamino)phenyl]propanoic acid
xref: CHEMBL4303708
synonym: CDP323
synonym: CDP-323
approved: f
ligand name: zaurategrast
type: SyntheticOrganicLigand

valategrast
in ch i key: VZVNFRFMDNFPOM-VWLOTQADSA-N
comment: Valategrast (RO-0272441) is an orally available, small molecule α4 integrin inhibitor that was developed by Roche <Reference id=41843/>. It is active at α4β1 and α4β7 integrins.
xref: CHEMBL2107792
synonym: RO-0272441
synonym: R-411
approved: f
ligand name: valategrast
type: SyntheticOrganicLigand

firategrast
in ch i key: YLFZHHDVRSYTKT-NRFANRHFSA-N
in ch i: InChI=1S/C27H27F2NO6/c1-4-36-15-17-13-22(34-2)24(23(14-17)35-3)18-10-8-16(9-11-18)12-21(27(32)33)30-26(31)25-19(28)6-5-7-20(25)29/h5-11,13-14,21H,4,12,15H2,1-3H3,(H,30,31)(H,32,33)/t21-/m0/s1
comment: Firategrast (SB-683699) is an orally bioavailable, short-acting small molecule α4-integrin antagonist. It was designed to reduce α4β1/α4β7 integrin-mediated trafficking of lymphocytes into the central nervous system (CNS). Anti-α4-integrin <Ligand id=6591/> is currently approved to treat MS, but its long half-life is problematic, and it has to be administered by infusion. This short acting small molecule was developed as an alternative to antibody therapy.
xref: CHEMBL2104967
synonym: SB-683699
synonym: SB683699
approved: f
ligand name: firategrast
type: SyntheticOrganicLigand

DM-CHX
in ch i key: OIJOPHJUWUWQSD-NZBPQXDJSA-N
in ch i: InChI=1S/C19H30N2O5/c1-11-5-12(2)19(26)14(6-11)15(22)7-13-8-16(23)21(17(24)9-13)10-18(25)20(3)4/h11-15,22H,5-10H2,1-4H3/t11-,12-,14-,15+/m0/s1
comment: DM-CHX is a selective inhibitor of FKBP38 <Reference id=41824/>.
iupac name: 2-[4-[(2R)-2-[(1S,3S,5S)-3,5-dimethyl-2-oxocyclohexyl]-2-hydroxyethyl]-2,6-dioxopiperidin-1-yl]-N,N-dimethylacetamide
synonym: N-(N′,N′-Dimethylcarboxamidomethyl)cycloheximide
approved: f
ligand name: DM-CHX
type: SyntheticOrganicLigand

GPI-1046
in ch i key: OQAHHWOPVDDWHD-INIZCTEOSA-N
in ch i: InChI=1S/C20H28N2O4/c1-4-20(2,3)17(23)18(24)22-12-6-10-16(22)19(25)26-13-7-9-15-8-5-11-21-14-15/h5,8,11,14,16H,4,6-7,9-10,12-13H2,1-3H3/t16-/m0/s1
comment: GPI-1046 was originally described to bind FKBP12 <Reference id=41823/>, but it has higher affinity for FKBP38 <Reference id=41824/>.
xref: CHEMBL6367
synonym: GPI1046
approved: f
ligand name: GPI-1046
type: SyntheticOrganicLigand

SAFit2
in ch i key: ZDBWLRLGUBSLPG-FDHYQTMZSA-N
in ch i: InChI=1S/C46H62N2O10/c1-51-39-20-18-32(28-40(39)52-2)17-19-38(34-14-11-15-36(29-34)57-27-24-47-22-25-56-26-23-47)58-46(50)37-16-9-10-21-48(37)45(49)43(33-12-7-6-8-13-33)35-30-41(53-3)44(55-5)42(31-35)54-4/h11,14-15,18,20,28-31,33,37-38,43H,6-10,12-13,16-17,19,21-27H2,1-5H3/t37-,38+,43-/m0/s1
comment: SAFit2 is a selective inhibitor of the FKBP51 PPIase <Reference id=41822/>.
iupac name: [(1R)-3-(3,4-dimethoxyphenyl)-1-[3-(2-morpholin-4-ylethoxy)phenyl]propyl] (2S)-1-[(2S)-2-cyclohexyl-2-(3,4,5-trimethoxyphenyl)acetyl]piperidine-2-carboxylate
xref: CHEMBL3623630
synonym: compound 2 [PMID: 25436518]
approved: f
ligand name: SAFit2
type: SyntheticOrganicLigand

SAFit1
in ch i key: OEQZPFWOEOOISR-AKTKKGGCSA-N
in ch i: InChI=1S/C42H53NO11/c1-48-34-20-18-27(22-35(34)49-2)17-19-33(29-14-11-15-31(23-29)53-26-38(44)45)54-42(47)32-16-9-10-21-43(32)41(46)39(28-12-7-6-8-13-28)30-24-36(50-3)40(52-5)37(25-30)51-4/h11,14-15,18,20,22-25,28,32-33,39H,6-10,12-13,16-17,19,21,26H2,1-5H3,(H,44,45)/t32-,33+,39-/m0/s1
comment: SAFit1 is a selective inhibitor of the FKBP51 PPIase <Reference id=41822/>.
iupac name: 2-[3-[(1R)-1-[(2S)-1-[(2S)-2-cyclohexyl-2-(3,4,5-trimethoxyphenyl)acetyl]piperidine-2-carbonyl]oxy-3-(3,4-dimethoxyphenyl)propyl]phenoxy]acetic acid
xref: CHEMBL3623612
synonym: compound 1 [PMID: 25436518]
approved: f
ligand name: SAFit1
type: SyntheticOrganicLigand

SLF
in ch i key: CKUAMXWZIHXZJC-LOSJGSFVSA-N
in ch i: InChI=1S/C32H41NO9/c1-6-32(2,3)29(36)30(37)33-17-8-7-12-24(33)31(38)42-25(22-10-9-11-23(19-22)41-20-28(34)35)15-13-21-14-16-26(39-4)27(18-21)40-5/h9-11,14,16,18-19,24-25H,6-8,12-13,15,17,20H2,1-5H3,(H,34,35)/t24-,25+/m0/s1
comment: SLF was the first small molecule synthetic ligand for FKBP51/52 <Reference id=41819/><Reference id=41820/>.
xref: CHEMBL321022
synonym: Synthetic Ligand for FKBP
synonym: compound 1a monomer [PMID: 12951089]
synonym: AP1510 monomer
synonym: ligand 2 [PMID: 22455398]
approved: f
ligand name: SLF
type: SyntheticOrganicLigand

retigabine derivative 10g
in ch i key: FWQHRZXEQNUCSY-UHFFFAOYSA-N
in ch i: InChI=1S/C24H28FN3O4/c1-6-14-28(16-17-8-10-18(25)11-9-17)19-12-13-20(26-22(29)31-7-2)21(15-19)27-23(30)32-24(3,4)5/h1,8-13,15H,7,14,16H2,2-5H3,(H,26,29)(H,27,30)
comment: Compound 10g is a potent Kv7.4 and Kv7.5 channel agonist <Reference id=41783/>. It does not potentiate activity of Kv7.1 or Kv7.2 channels.
iupac name: tert-butyl N-[2-(ethoxycarbonylamino)-5-[(4-fluorophenyl)methyl-prop-2-ynylamino]phenyl]carbamate
xref: CHEMBL4588394
synonym: compound 10g [PMID: 30655942]
approved: f
ligand name: retigabine derivative 10g
type: SyntheticOrganicLigand

RY785
in ch i key: LDXZFQWWXMRMAS-OAHLLOKOSA-N
in ch i: InChI=1S/C21H27N3O2/c1-14(2)20(25)23-17-11-12-19(24(4)5)18(13-17)21(26)22-15(3)16-9-7-6-8-10-16/h6-15H,1-5H3,(H,22,26)(H,23,25)/t15-/m1/s1
comment: Herringtom et al. (2011) stipulates that RY785 is the (R) enantiomer, and RY796 is the (S) enantiomer <Reference id=25622/>.
iupac name: 2-(dimethylamino)-5-(2-methylpropanoylamino)-N-[(1R)-1-phenylethyl]benzamide
approved: f
ligand name: RY785
type: SyntheticOrganicLigand

JNJ303
in ch i key: OSGIRCJRKSAODN-YLGPJNIESA-N
comment: JNJ303 is a selective blocker of the Kv7.1 current <Reference id=41784/>.
iupac name: 2-(4-chlorophenoxy)-N-[5-(methanesulfonamido)-2-adamantyl]-2-methylpropanamide
synonym: JNJ 303
synonym: JNJ-303
approved: f
ligand name: JNJ303
type: SyntheticOrganicLigand

NS383
in ch i key: CHVQAXYXYIDNDC-UHFFFAOYSA-N
in ch i: InChI=1S/C19H19N3O2/c1-2-22-9-8-13-14(12-6-4-3-5-7-12)10-15-17(16(13)11-22)20-19(23)18(15)21-24/h3-7,10,24H,2,8-9,11H2,1H3,(H,20,21,23)
comment: NS383 inhibits acid‐sensing ion channels (ASICs) that contain 1a and 3 subunits <Reference id=41777/>.
iupac name: (3E)-8-ethyl-3-(hydroxyimino)-5-phenyl-1H,2H,3H,6H,7H,8H,9H-pyrrolo[3,2-h]isoquinolin-2-one
approved: f
ligand name: NS383
type: SyntheticOrganicLigand

JNJ-67869386
in ch i key: YINCAUPIZHIQGR-UHFFFAOYSA-N
in ch i: InChI=1S/C16H15F2N5O/c1-8-2-14(12(18)5-20-8)23-6-10(7-23)24-9-3-11(17)15-13(4-9)21-22-16(15)19/h2-5,10H,6-7H2,1H3,(H3,19,21,22)
comment: JNJ-67869386 is an allosteric antagonist of the ASIC1a ion channel <Reference id=41776/>.
iupac name: 4-fluoro-6-{[1-(5-fluoro-2-methylpyridin-4-yl)azetidin-3-yl]oxy}-1H-indazol-3-amine
approved: f
ligand name: JNJ-67869386
type: SyntheticOrganicLigand

R(-)amphetamine
canonical SMILES: CC(Cc1ccccc1)N
isomeric SMILES: C[C@H](Cc1ccccc1)N
in ch i key: KWTSXDURSIMDCE-MRVPVSSYSA-N
in ch i: InChI=1S/C9H13N/c1-8(10)7-9-5-3-2-4-6-9/h2-6,8H,7,10H2,1H3/t8-/m1/s1
iupac name: (2R)-1-phenylpropan-2-amine
xref: CHEMBL19393
synonym: l-amphetamine
approved: f
ligand name: R(-)amphetamine
type: SyntheticOrganicLigand

JNJ-799760
in ch i key: QMVSFWHTZQVRCC-UHFFFAOYSA-N
in ch i: InChI=1S/C22H20N4O3/c1-27-19-10-8-16(12-20(19)28-2)29-15-6-3-13(4-7-15)22-25-17-9-5-14(21(23)24)11-18(17)26-22/h3-12H,1-2H3,(H3,23,24)(H,25,26)
comment: JNJ-799760 is an allosteric antagonist of the ASIC1a ion channel <Reference id=41776/>.
iupac name: 2-[4-(3,4-dimethoxyphenoxy)phenyl]-3H-benzimidazole-5-carboximidamide
approved: f
ligand name: JNJ-799760
type: SyntheticOrganicLigand

compound 5b [PMID: 25974655]
in ch i key: VVYLUODGYRRACW-UHFFFAOYSA-N
in ch i: InChI=1S/C23H27ClN4O2/c1-3-27(4-2)11-12-28(15-16-5-8-18(24)9-6-16)19-10-7-17-13-20(22(25)26)23(29)30-21(17)14-19/h5-10,13-14H,3-4,11-12,15H2,1-2H3,(H3,25,26)
comment: Compound 5b (synthesised as the dihydrochloride salt) is an orthosteric antagonist of ASIC1a ion channel <Reference id=41775/>.
iupac name: 7-[(4-chlorophenyl)methyl-[2-(diethylamino)ethyl]amino]-2-oxochromene-3-carboximidamide
xref: CHEMBL3577296
approved: f
ligand name: compound 5b [PMID: 25974655]
type: SyntheticOrganicLigand

citronellal
canonical SMILES: O=CCC(CCC=C(C)C)C
isomeric SMILES: O=CCC(CCC=C(C)C)C
in ch i key: NEHNMFOYXAPHSD-UHFFFAOYSA-N
in ch i: InChI=1S/C10H18O/c1-9(2)5-4-6-10(3)7-8-11/h5,8,10H,4,6-7H2,1-3H3
comment: Citronellal is a plant monoterpenoid, responsible for the lemon scent of citronella oil.
iupac name: 3,7-dimethyloct-6-enal
synonym: rhodinal
synonym: 3,7-dimethyl-6-octenal
approved: f
ligand name: citronellal
type: SyntheticOrganicLigand

BRD9185
in ch i key: FYPZBZFXJUJJRA-AQNXPRMDSA-N
in ch i: InChI=1S/C23H21F6N3O2/c1-2-9-31-21(34)32-18(11-30)20(19(32)12-33)14-5-3-13(4-6-14)15-7-8-16(22(24,25)26)17(10-15)23(27,28)29/h3-8,10,18-20,33H,2,9,12H2,1H3,(H,31,34)/t18-,19-,20+/m1/s1
comment: BRD9185 is the optimized lead from a novel structural class of P. falciparum dihydroorotate dehydrogenase (PfDHODH) inhibitors with potent antimalarial activity <Reference id=41755/>. Chemically it is a azetidine-2-carbonitrile compound. The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
iupac name: (2S,3S,4S)-3-[4-[3,4-bis(trifluoromethyl)phenyl]phenyl]-2-cyano-4-(hydroxymethyl)-N-propylazetidine-1-carboxamide
xref: CHEMBL4064731
synonym: compound 27 [PMID: 28435533]
approved: f
ligand name: BRD9185
type: SyntheticOrganicLigand

tilarginine
canonical SMILES: CN=C(NCCC[C@@H](C(=O)O)N)N
isomeric SMILES: CN=C(NCCC[C@@H](C(=O)O)N)N
in ch i key: NTNWOCRCBQPEKQ-YFKPBYRVSA-N
in ch i: InChI=1S/C7H16N4O2/c1-10-7(9)11-4-2-3-5(8)6(12)13/h5H,2-4,8H2,1H3,(H,12,13)(H3,9,10,11)/t5-/m0/s1
comment: Tilarginine acts as a pan-nitric oxide synthase (NOS) inhibitor. Chemically it is a conformationally restricted arginine analogue <Reference id=41733/>. It was investigated for potential immunomodulating and antineoplastic activities.
iupac name: (2S)-2-amino-5-[(N'-methylcarbamimidoyl)amino]pentanoic acid
xref: CHEMBL256147
synonym: N(G)-monomethyl L-arginine
synonym: L-Monomethylarginine
synonym: L-NMA
synonym: targinine (deprecated INN)
approved: f
ligand name: tilarginine
type: SyntheticOrganicLigand

MMV689258
in ch i key: HCDITNRDWJWQAL-MLGOLLRUSA-N
in ch i: InChI=1S/C18H27FN2O4/c1-12(10-20-17(25)16(24)18(2,3)11-22)21-15(23)9-8-13-6-4-5-7-14(13)19/h4-7,12,16,22,24H,8-11H2,1-3H3,(H,20,25)(H,21,23)/t12-,16-/m1/s1
comment: MMV689258 is the lead compound from a new class of pantothenamides that are resistant to inactivation by serum pantetheinases <Reference id=41574/>.
iupac name: (2S)-N-[(2R)-2-[3-(2-fluorophenyl)propanoylamino]propyl]-2,4-dihydroxy-3,3-dimethylbutanamide
approved: f
ligand name: MMV689258
type: SyntheticOrganicLigand

MMV009108
in ch i key: CFAYJTHICHSZHC-UHFFFAOYSA-N
in ch i: InChI=1S/C21H25N3O2S2/c1-5-24(6-2)28(25,26)19-11-8-17(9-12-19)20-14-27-21(23-20)22-18-10-7-15(3)16(4)13-18/h7-14H,5-6H2,1-4H3,(H,22,23)
comment: MMV009108 is a drug-like compound that was chosen as one of the chemotypes included in the MMV Malaria Box <Reference id=38140/>. It is one of three structurally diverse small molecules that have been shown to inhibit P. falciparum Niemann-Pick type C1-related protein (PfNCR1) <Reference id=38647/>. The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
iupac name: 4-[2-[(3,4-dimethylphenyl)amino]-1,3-thiazol-4-yl]-N,N-diethylbenzenesulfonamide
xref: CHEMBL1198449
synonym: GNF-Pf-3616
approved: f
ligand name: MMV009108
type: SyntheticOrganicLigand

compound 4 [PMID: 30824200]
canonical SMILES: CCc1cc(O)cc2c1[nH]cc2/C=N/NC(=N)NCCc1ccc(cc1)C
isomeric SMILES: CCc1cc(O)cc2c1[nH]cc2/C=N/NC(=N)NCCc1ccc(cc1)C
in ch i key: FEOVKCUPOVFERI-DHRITJCHSA-N
in ch i: InChI=1S/C21H25N5O/c1-3-16-10-18(27)11-19-17(12-24-20(16)19)13-25-26-21(22)23-9-8-15-6-4-14(2)5-7-15/h4-7,10-13,24,27H,3,8-9H2,1-2H3,(H3,22,23,26)/b25-13+
comment: Compound 4 is small molecule agonist of the relaxin receptors RXFP3 and RXFP4 <Reference id=41711/>. It increases food intake in rats.
iupac name: N-[(E)-[(7-ethyl-5-hydroxy-1H-indol-3-yl)methylidene]amino]-N'-[2-(4-methylphenyl)ethyl]guanidine
approved: f
ligand name: compound 4 [PMID: 30824200]
type: SyntheticOrganicLigand

JK1
in ch i key: USSMQJUVPNGHNK-IBGZPJMESA-N
in ch i: InChI=1S/C21H17ClN4O2/c22-15-5-2-1-4-14(15)20-24-21-23-16-6-3-7-17(28)18(16)19(26(21)25-20)12-8-10-13(27)11-9-12/h1-2,4-5,8-11,19,27H,3,6-7H2,(H,23,24,25)/t19-/m0/s1
comment: JK1 is a small molecule agonist of the relaxin family peptide receptor 4 (RXFP4) <Reference id=41712/>.
iupac name: (9S)-2-(2-chlorophenyl)-9-(4-hydroxyphenyl)-4H,5H,6H,7H,8H,9H-[1,2,4]triazolo[3,2-b]quinazolin-8-one
synonym: (S)-JK0621-D008
approved: f
ligand name: JK1
type: SyntheticOrganicLigand

CC-401
in ch i key: XDJCLCLBSGGNKS-UHFFFAOYSA-N
in ch i: InChI=1S/C22H24N6O/c1-2-9-28(10-3-1)11-12-29-18-6-4-5-16(13-18)21-19-14-17(22-23-15-24-27-22)7-8-20(19)25-26-21/h4-8,13-15H,1-3,9-12H2,(H,25,26)(H,23,24,27)
comment: CC-401 was originally identified as a c-Jun N-terminal kinase (JNK) inhibitor. It was developed by Celgene who advanced it into clinical trial for anti-leukemia potential <Reference id=41579/>, but this programme was abandoned. CC-401 was subsequently found to inhibit DYRK1A and DYRK1B <Reference id=41578/>. It promotes replication of pancreatic β-cells in vitro (rat and human) and in vivo (rat) via DYRK1A/B-dependent mechanisms.
xref: CHEMBL1614713
synonym: CC401
approved: f
ligand name: CC-401
type: SyntheticOrganicLigand

MMV019313
in ch i key: NVFMMXVDSJFVNO-UHFFFAOYSA-N
in ch i: InChI=1S/C22H27N3O2S/c1-24-18-10-5-4-9-16(18)20-17(22(24)27)15-19(28-20)21(26)23-11-8-14-25-12-6-2-3-7-13-25/h4-5,9-10,15H,2-3,6-8,11-14H2,1H3,(H,23,26)
comment: MMV019313 is a drug-like compound that was chosen as one of the chemotypes included in the MMV Malaria Box <Reference id=38140/>. It is the first non-bisphosphonate inhibitor of P. falciparum bifunctional farnesyl/geranylgeranyl diphosphate synthase (PfFPPS/GGPPS) to be described and is highly selective for the Plasmodium target <Reference id=41772/>. The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
iupac name: N-[3-(azepan-1-yl)propyl]-5-methyl-4-oxothieno[3,2-c]quinoline-2-carboxamide
xref: CHEMBL532155
synonym: TCMDC-123889
approved: f
ligand name: MMV019313
type: SyntheticOrganicLigand

DDD85646
in ch i key: XMBSZPZJLPTFMV-UHFFFAOYSA-N
comment: The pyrazole sulfonamide, DDD85646, was first identified as a potent N-myristoyltransferase (NMT) inhibitor in T. brucei, the parasite that causes African sleeping sickness (trypanosomiasis) <Reference id=41821/>. The compound also has antimalarial activity <Reference id=35010/>. The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
iupac name: 2,6-dichloro-4-(2-piperazin-1-ylpyridin-4-yl)-N-(1,3,5-trimethylpyrazol-4-yl)benzenesulfonamide
xref: CHEMBL1230468
synonym: compound 1a [PMID: 24451586]
synonym: IMP-366
approved: f
ligand name: DDD85646
type: SyntheticOrganicLigand

selepressin
in ch i key: JCVQBJTWWDYUFQ-MRUTUVJXSA-N
comment: Selepressin (FE 202158) is a peptidic vasopressin V1A receptor full agonist <Reference id=41561/>.
xref: CHEMBL1817709
synonym: FE202158
approved: f
ligand name: selepressin
type: PeptideLigand

MRS4625
in ch i key: AHFBZYAJIRDUHZ-UHFFFAOYSA-N
in ch i: InChI=1S/C30H26F3NO3/c1-37-34-14-12-21(13-15-34)19-2-4-22(5-3-19)28-18-25(29(35)36)17-24-16-23(8-11-27(24)28)20-6-9-26(10-7-20)30(31,32)33/h2-11,16-18,21H,12-15H2,1H3,(H,35,36)
comment: MRS4625 is a selective P2Y14 receptor antagonist <Reference id=41556/>.
iupac name: 4-[4-(1-methoxypiperidin-4-yl)phenyl]-7-[4-(trifluoromethyl)phenyl]naphthalene-2-carboxylic acid
synonym: compound 4 [PMID: 32551012]
synonym: MRS-4625
approved: f
ligand name: MRS4625
type: SyntheticOrganicLigand

TIM-38
canonical SMILES: [O-][N+](=O)C1=Cc2ccccc2OC1C(F)(F)F
isomeric SMILES: [O-][N+](=O)C1=Cc2ccccc2OC1C(F)(F)F
in ch i key: BGTJUOYBNMSGRC-UHFFFAOYSA-N
in ch i: InChI=1S/C10H6F3NO3/c11-10(12,13)9-7(14(15)16)5-6-3-1-2-4-8(6)17-9/h1-5,9H
comment: TIM-38 is a P2Y6 receptor selective antagonist <Reference id=41555/>.
iupac name: 3-nitro-2-(trifluoromethyl)-2H-chromene
synonym: TIM38
approved: f
ligand name: TIM-38
type: SyntheticOrganicLigand

5H78PF
canonical SMILES: O=C1CC(Oc2c1c(O)cc1c2C=CCO1)c1ccccc1
isomeric SMILES: O=C1CC(Oc2c1c(O)cc1c2C=CCO1)c1ccccc1
in ch i key: USERNAUADQTGOU-UHFFFAOYSA-N
in ch i: InChI=1S/C18H14O4/c19-13-9-15(11-5-2-1-3-6-11)22-18-12-7-4-8-21-16(12)10-14(20)17(13)18/h1-7,10,15,20H,8-9H2
comment: 5H78PF is a small-molecule probe that can be used to explore the active site cavity of cytochrome P450 enzyme 1A2 <Reference id=29717/>.
iupac name: 5-hydroxy-2-phenyl-2H,3H,4H,8H-pyrano[2,3-f]chromen-4-one
approved: f
ligand name: 5H78PF
type: SyntheticOrganicLigand

ciclopirox
canonical SMILES: Cc1cc(C2CCCCC2)n(c(=O)c1)O
isomeric SMILES: Cc1cc(C2CCCCC2)n(c(=O)c1)O
in ch i key: SCKYRAXSEDYPSA-UHFFFAOYSA-N
in ch i: InChI=1S/C12H17NO2/c1-9-7-11(13(15)12(14)8-9)10-5-3-2-4-6-10/h7-8,10,15H,2-6H2,1H3
comment: Ciclopirox was originally developed as an antifungal drug. It also has anti-inflammatory activity, which is potentially mediated via inhibition of PARP-1.
iupac name: 6-cyclohexyl-1-hydroxy-4-methylpyridin-2-one
xref: CHEMBL1413
synonym: Ciclodan®
synonym: Loprox®
synonym: HOE-296
synonym: HOE-296b
approved: t
ligand name: ciclopirox
type: SyntheticOrganicLigand

PSB-16133
in ch i key: QXOGPTXQGKQSJT-UHFFFAOYSA-N
in ch i: InChI=1S/C28H22N2O5S2/c1-15-7-10-19(13-16(15)2)36-18-11-8-17(9-12-18)30-22-14-23(37(33,34)35)26(29)25-24(22)27(31)20-5-3-4-6-21(20)28(25)32/h3-14,30H,29H2,1-2H3,(H,33,34,35)
comment: PSB-16133 is a P2Y4 receptor selective antagonist <Reference id=41554/>. We show the chemical structure for the parent molecule. It also appears in online chemistry resources as the sodium sulphonate (PubChem CID 132574706)
iupac name: 1-amino-4-[4-(3,4-dimethylphenyl)sulfanylanilino]-9,10-dioxoanthracene-2-sulfonic acid
xref: CHEMBL4116316
synonym: PSB16133
synonym: compound 61 [PMID: 28306255]
approved: f
ligand name: PSB-16133
type: SyntheticOrganicLigand

serdexmethylphenidate
in ch i key: UBZPNQRBUOBBLN-PWRODBHTSA-N
in ch i: InChI=1S/C25H29N3O8/c1-35-24(33)21(17-8-3-2-4-9-17)20-11-5-6-13-28(20)25(34)36-16-27-12-7-10-18(14-27)22(30)26-19(15-29)23(31)32/h2-4,7-10,12,14,19-21,29H,5-6,11,13,15-16H2,1H3,(H-,26,30,31,32)/t19-,20+,21+/m0/s1
comment: Serdexmethylphenidate (KP484) is a prodrug that is a slow-release derivative of <Ligand id=7554/> (d-MPH).
iupac name: (2S)-3-hydroxy-2-[[1-[[(2R)-2-[(1R)-2-methoxy-2-oxo-1-phenylethyl]piperidine-1-carbonyl]oxymethyl]pyridin-1-ium-3-carbonyl]amino]propanoate
synonym: KP484
synonym: KP-484
synonym: Azstarys® (serdexmethylphenidate + dexmethylphenidate)
approved: t
ligand name: serdexmethylphenidate
type: SyntheticOrganicLigand

[3H]T-516
in ch i key: YYZIODGIFUUQEK-INRSUVRLSA-N
in ch i: InChI=1S/C18H34N2O4S/c1-4-13-8-10-14(11-9-13)24-12-16-15(18(21)19-2)6-5-7-17(16)20-25(3,22)23/h13-17,20H,4-12H2,1-3H3,(H,19,21)/t13-,14+,15?,16-,17+/m1/s1/i2T
comment: [3H]T-516 is a tritium-labelled OX2R agonist <Reference id=41540/>. Its chemical structure is similar to that of <Ligand id=11448/>.
iupac name: (2R,3S)-3-methanesulfonamido-N-methyl-2-({[(1r,4s)-4-ethylcyclohexyl]oxy}methyl)cyclohexane-1-carboxamide
approved: f
ligand name: [3H]T-516
type: SyntheticOrganicLigand

TAK-925
in ch i key: UXZAJSZFFARTEI-YRPNKDGESA-N
in ch i: InChI=1S/C21H32N2O5S/c1-27-21(24)23-14-6-9-19(22-29(2,25)26)20(23)15-28-18-12-10-17(11-13-18)16-7-4-3-5-8-16/h3-5,7-8,17-20,22H,6,9-15H2,1-2H3/t17-,18+,19-,20-/m0/s1
comment: TAK-925 is a selective orexin 2 receptor agonist. We drew the structure form the image presented in <Reference id=41540/>. This maps to the INN danavorexton via PubChem.
synonym: TAK925
synonym: Example 5 [US10287305]
approved: f
ligand name: TAK-925
type: SyntheticOrganicLigand

compound 1 [PMID: 33547286]
in ch i key: AMTAVIZAVFJXIJ-UHFFFAOYSA-N
in ch i: InChI=1S/C33H32N6O5S/c1-38(2)33(41)26-10-7-9-24(21-26)25-14-15-30(44-3)31(22-25)45(42,43)37-27-11-6-8-23(20-27)16-17-34-32(40)28-12-4-5-13-29(28)39-35-18-19-36-39/h4-15,18-22,37H,16-17H2,1-3H3,(H,34,40)
comment: Compound 1 is a small molecule orexin receptor agonist, with selectivity for OX2 <Reference id=41539/>. Cryo-EM reveals that it binds to the orthosteric pocket of the OX2 receptor and stabilises the active receptor conformation.
approved: f
ligand name: compound 1 [PMID: 33547286]
type: SyntheticOrganicLigand

GS-441524
in ch i key: BRDWIEOJOWJCLU-LTGWCKQJSA-N
in ch i: InChI=1S/C12H13N5O4/c13-4-12(10(20)9(19)7(3-18)21-12)8-2-1-6-11(14)15-5-16-17(6)8/h1-2,5,7,9-10,18-20H,3H2,(H2,14,15,16)/t7-,9-,10-,12+/m1/s1
comment: GS-441524 is the parent nucleoside that is metabolically liberated from <Ligand id=10715/>. Both compounds block RNA transcription by inhibiting the viral RNA-dependent RNA polymerase (RdRP). GS-441524 is the major metabolite and persists in the circulation with a longer half-life than remdesivir. GS-441524 potently inhibits SARS-CoV-2 replication in in vitro and in vivoinfection models <Reference id=41535/>.
xref: CHEMBL2016757
synonym: GS441524
synonym: EVO-984
synonym: EVO984
approved: f
ligand name: GS-441524
type: SyntheticOrganicLigand

compound 5 [Zhang et al., 2021]
in ch i key: KFGXONJZGIXSGH-UHFFFAOYSA-N
in ch i: InChI=1S/C26H20ClN3O2/c1-2-10-32-23-12-19(11-21(27)14-23)25-13-20(24-8-4-3-6-18(24)15-28)17-30(26(25)31)22-7-5-9-29-16-22/h3-9,11-14,16-17H,2,10H2,1H3
comment: Compound 5 is a non-covalent SARS-CoV-2 Mpro (3CL-pro) inhibitor with in vitro antiviral activity <Reference id=41534/>. It appears to provide synergistic antiviral activity with the viral polymerase inhibitor <Ligand id=10715/> in vitro, in a replicon assay that utilised a non-infectious SARS-CoV-2 clone. Structurally, 5 is a derivative of the anticonvulsant drug <Ligand id=7050/>, and was designed to optimise perampanel's weak (IC50100-250 μM) Mpro inhibitory activity. Several nM potency inhibitors were identified in this study (e.g. 21, IC50 18 nM in an enzyme kinetic assay), but they did not deliver antiviral activity in the in vitro assays and/or were cytotoxic. Compound 26 with 1 μM antiviral activity and no cytotoxicity was highlighted as a significant lead structure. The crystal structure of 5 bound to SARS-CoV-2 Mpro has been resolved to 1.8 Å and was submitted to the Protein Data Bank with accession ID 7L11.
iupac name: 2-(3-(3-Chloro-5-propoxyphenyl)-2-oxo-2H [1,3'-bipyridin]-5-yl)benzonitrile
approved: f
ligand name: compound 5 [Zhang et al., 2021]
type: SyntheticOrganicLigand

MI-30
in ch i key: HKJKOHDJUKCNRG-ZEAPZOAHSA-N
comment: MI-30 is one of the SARS-CoV-2 Mpro (3CL-pro) inhibitors reported in <Reference id=41460/>. The most potent inhibitor of Mpro activity was <Ligand id=11432/>, but <Ligand id=11440/> and MI-30 were taken into in vivo studies that revealed that they had antiviral activity, and reduced both lung viral loads and lung lesions in infected mice.
iupac name: (1S,3aR,6aS)-2-(2-(2,4-dichlorophenoxy)acetyl)-N-((S)-1-oxo-3-((S)-2-oxopyrrolidin-3-yl)propan-2-yl)octahydrocyclopenta[c]pyrrole-1-carboxamide
synonym: compound 18p [PMID:33602867]
approved: f
ligand name: MI-30
type: SyntheticOrganicLigand

MI-09
in ch i key: RBWMYPKAPIYTJQ-VMBFOHBNSA-N
in ch i: InChI=1S/C24H28F3N3O6/c1-23(2)17-10-30(18(32)12-35-15-3-5-16(6-4-15)36-24(25,26)27)20(19(17)23)22(34)29-14(11-31)9-13-7-8-28-21(13)33/h3-6,11,13-14,17,19-20H,7-10,12H2,1-2H3,(H,28,33)(H,29,34)/t13-,14-,17-,19-,20-/m0/s1
comment: MI-09 is a SARS-CoV-2 Mpro (3CL-pro) inhibitor that was reported in the same study as <Ligand id=11432/> <Reference id=41460/>. MI-09 exhibited in vivo antiviral activity, and reduced both lung viral loads and lung lesions in infected mice.
iupac name: (1R,2S,5S)-6,6-dimethyl-N-[(2S)-1-oxo-3-[(3S)-2-oxopyrrolidin-3-yl]propan-2-yl]-3-{2-[4-(trifluoromethoxy)phenoxy]acetyl}-3-azabicyclo[3.1.0]hexane-2-carboxamide
synonym: compound 11i [PMID: 33602867]
approved: f
ligand name: MI-09
type: SyntheticOrganicLigand

RCI-0879
in ch i key: ABDQSBVMVCODPZ-IBGZPJMESA-N
comment: RCI-0879 is a non-peptide small molecule antagonist of the urotensin-II receptor <Reference id=41492/>. It is active in vitro and in vivo.
iupac name: 6,7-dichloro-4-{2-[(2S)-4-[2-(morpholin-4-yl)ethanesulfonyl]-2-[(pyrrolidin-1-yl)methyl]piperazin-1-yl]-2-oxoethyl}-3,4-dihydro-2H-1,4-benzoxazin-3-one
synonym: RCI0879
approved: f
ligand name: RCI-0879
type: SyntheticOrganicLigand

DS37001789
in ch i key: WDLHORHSBVXUET-FQEVSTJZSA-N
comment: DS37001789 is an orally bioactive urotensin II receptor antagonist <Reference id=41491/>. It is active in vivo <Reference id=41490/>.
iupac name: 1-[(2S)-4-[2-(4-acetylpiperazin-1-yl)ethanesulfonyl]-2-[(pyrrolidin-1-yl)methyl]piperazin-1-yl]-2-(2,4,5-trichlorophenoxy)ethan-1-one
approved: f
ligand name: DS37001789
type: SyntheticOrganicLigand

VU0409551
in ch i key: QUZLMKNNIUSREV-UHFFFAOYSA-N
in ch i: InChI=1S/C20H17FN2O3/c21-15-8-6-14(7-9-15)20(24)23-11-10-17-18(12-23)26-19(22-17)13-25-16-4-2-1-3-5-16/h1-9H,10-13H2
comment: VU0409551 is a mGlu5 positive allosteric modulator (PAM) <Reference id=41483/>.
iupac name: (4-fluorophenyl)-[2-(phenoxymethyl)-6,7-dihydro-4H-[1,3]oxazolo[5,4-c]pyridin-5-yl]methanone
synonym: JNJ-46778212
synonym: JNJ46778212
approved: f
ligand name: VU0409551
type: SyntheticOrganicLigand

[125I]bantag-1
in ch i key: DAWSYEXBFLQUER-SLMIJXFKSA-P
in ch i: InChI=1S/C49H80N8O7/c1-33(2)23-40(45(60)51-29-36-21-16-22-37(24-36)31-57(7,8)9)53-44(59)28-43(58)39(25-34-17-12-10-13-18-34)54-46(61)42(27-38-30-50-32-52-38)56(6)47(62)41(26-35-19-14-11-15-20-35)55-48(63)64-49(3,4)5/h11,14,19,21,24,30,32-34,39-43,46,54,58,61H,10,12-13,15-18,20,22-23,25-29,31H2,1-9H3,(H3-,50,51,52,53,55,59,60,63)/p+2/t39-,40-,41-,42-,43-,46?/m0/s1
comment: A radiolabelled version of <Ligand id=6176/> that can be used as a selective tracer for BB3 receptors <Reference id=40545/>. It is >10,000-fold selective for BB3 over the other two mammalian bombesin receptors.
approved: f
ligand name: [125I]bantag-1
type: SyntheticOrganicLigand

cetilistat
canonical SMILES: CCCCCCCCCCCCCCCCOc1nc2ccc(cc2c(=O)o1)C
isomeric SMILES: CCCCCCCCCCCCCCCCOc1nc2ccc(cc2c(=O)o1)C
in ch i key: MVCQKIKWYUURMU-UHFFFAOYSA-N
comment: Cetilistat (ATL-962) is an orally active anti-obesity drug, that was designed to inhibit gastrointestinal and pancreatic lipases <Reference id=41461/><Reference id=41462/>. Its mechanism of action is similar to that of <Ligand id=5277/>. SARS-CoV-2: in a large scale screen of approved drugs, cetilistat exhibited potent in vitro anti-SARS-CoV-2 activity (EC50 1.13 μM in a plaque reduction assay) and dose-dependently reduced viral load <Reference id=41464/>.
iupac name: 2-hexadecoxy-6-methyl-3,1-benzoxazin-4-one
synonym: ATL-962
synonym: ATL962
synonym: Oblean®
approved: t
ligand name: cetilistat
type: SyntheticOrganicLigand

MI-23
in ch i key: ZUAZJPLYYVHKFN-NAFADOBPSA-N
in ch i: InChI=1S/C24H29F2N3O4/c25-17-8-14(9-18(26)11-17)4-5-21(31)29-12-16-2-1-3-20(16)22(29)24(33)28-19(13-30)10-15-6-7-27-23(15)32/h8-9,11,13,15-16,19-20,22H,1-7,10,12H2,(H,27,32)(H,28,33)/t15-,16-,19-,20-,22-/m0/s1
comment: MI-23 is the most potent of the SARS-CoV-2 Mpro (3CL-pro) inhibitors reported in <Reference id=41460/>. <Ligand id=11440/> and <Ligand id=11441/> from the same study exhibited in vivo antiviral activity, and reduced both lung viral loads and lung lesions in infected mice.
synonym: compound 18i [PMID: 33602867]
approved: f
ligand name: MI-23
type: SyntheticOrganicLigand

triheptanoin
in ch i key: PJHKBYALYHRYSK-UHFFFAOYSA-N
in ch i: InChI=1S/C24H44O6/c1-4-7-10-13-16-22(25)28-19-21(30-24(27)18-15-12-9-6-3)20-29-23(26)17-14-11-8-5-2/h21H,4-20H2,1-3H3
comment: Triheptanoin is a medium-chain triglyceride that is administered as a rescue therapeutic in patients with long-chain fatty acid oxidation disorders <Reference id=41457/>.
iupac name: 2,3-di(heptanoyloxy)propyl heptanoate
xref: CHEMBL4297585
synonym: UX-007
synonym: UX007
synonym: Dojolvi®
approved: t
ligand name: triheptanoin
type: SyntheticOrganicLigand

viltolarsen
in ch i key: ZVXLKCOOOKREJD-OERAVCCFSA-N
comment: Viltolarsen is an antisense phosphorodiamidate morpholino oligomer (PMO) class nucleotide drug. Its abbreviated chemical/nucleotide structure is all-P-ambo-[2',3'-azanediyl-P,2',3'-trideoxy-P-(dimethylamino)-2',3'-seco](2'-N→5')(CCTCCGGTTCTGAAGGTGTTC). Viltolarsen restores the reading frame of certain dystrophin gene mutations and promotes synthesis of a shorter but functional dystrophin protein.
synonym: Viltepso®
synonym: NS-065
synonym: NCNP-01
approved: t
ligand name: viltolarsen
type: SyntheticOrganicLigand

tirzepatide
in ch i key: AAPYRSPHYSKGIS-MCNPHUAVSA-N
comment: Tirzepatide (LY3298176) is a clinical stage dual GIP/GLP-1 agonist ('twincretin'), that was developed to help manage type 2 diabetes mellitus (T2DM) <Reference id=41453/><Reference id=41452/> and as a novel anti-obesity medication. Structurally it is 39 amino acid linear peptide that is conjugated to a C20 fatty diacid moiety by a linker connected to the lysine20 residue. The dual agonist approach produces a synergistic effect on the insulin and glucagonostatic responses compared to a GLP-1 agonist (<Ligand id=9724/>) alone <Reference id=41453/><Reference id=41454/>. It was the first dual-targeting single agent to be approved for T2DM management.
synonym: LY3298176
synonym: LY-3298176
synonym: Mounjaro®
approved: t
ligand name: tirzepatide
type: PeptideLigand

posaconazole
in ch i key: RAGOYPUPXAKGKH-XAKZXMRKSA-N
in ch i: InChI=1S/C37H42F2N8O4/c1-3-35(26(2)48)47-36(49)46(25-42-47)31-7-5-29(6-8-31)43-14-16-44(17-15-43)30-9-11-32(12-10-30)50-20-27-19-37(51-21-27,22-45-24-40-23-41-45)33-13-4-28(38)18-34(33)39/h4-13,18,23-27,35,48H,3,14-17,19-22H2,1-2H3/t26-,27+,35-,37-/m0/s1
comment: Posaconazole is a broad-spectrum, second generation, antifungal drug. It inhibits the fungal lanosterol 14α-demethylase, which reduces production of ergosterol (an important component of the fungal cell wall).
iupac name: 4-[4-[4-[4-[[(3R,5R)-5-(2,4-difluorophenyl)-5-(1,2,4-triazol-1-ylmethyl)oxolan-3-yl]methoxy]phenyl]piperazin-1-yl]phenyl]-2-[(2S,3S)-2-hydroxypentan-3-yl]-1,2,4-triazol-3-one
xref: CHEMBL1397
synonym: Noxafil®
synonym: SCH56592
synonym: SCH-56592
synonym: Schering 56592
approved: t
ligand name: posaconazole
type: SyntheticOrganicLigand

oseltamivir
in ch i key: VSZGPKBBMSAYNT-RRFJBIMHSA-N
in ch i: InChI=1S/C16H28N2O4/c1-5-12(6-2)22-14-9-11(16(20)21-7-3)8-13(17)15(14)18-10(4)19/h9,12-15H,5-8,17H2,1-4H3,(H,18,19)/t13-,14+,15+/m0/s1
comment: Oseltamivir is an oral antiviral prodrug. Its active metabolite inhibits influenza neuraminidases and prevents new viral particles from being released from infected host cells.
iupac name: ethyl (3R,4R,5S)-4-acetamido-5-amino-3-pentan-3-yloxycyclohexene-1-carboxylate
xref: CHEMBL1229
synonym: Tamiflu®
synonym: Tamvir®
synonym: GS-4104
synonym: GS4104
synonym: RO-640796
synonym: RO640796
approved: t
ligand name: oseltamivir
type: SyntheticOrganicLigand

itraconazole
in ch i key: VHVPQPYKVGDNFY-ZPGVKDDISA-N
comment: Itraconazole is an antimycotic drug. It inhibits fungal cytochrome P450 enzymes. It has been reported to exhibit antiviral activity towards SARS-CoV-2 (in VERO-E6 cells), potentially via inhibition of the virus' main protease (M-Pro, 3CL-Pro).
iupac name: 2-butan-2-yl-4-[4-[4-[4-[[(2R,4S)-2-(2,4-dichlorophenyl)-2-(1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]piperazin-1-yl]phenyl]-1,2,4-triazol-3-one
xref: CHEMBL22587
synonym: Sporanox®
synonym: R-51211
synonym: R51211
synonym: ITZ
approved: t
ligand name: itraconazole
type: SyntheticOrganicLigand

BW B70C
canonical SMILES: Fc1ccc(cc1)Oc1cccc(c1)/C=C/C(N(C(=O)N)O)C
isomeric SMILES: Fc1ccc(cc1)Oc1cccc(c1)/C=C/C(N(C(=O)N)O)C
in ch i key: UAIYNMRLUHHRMF-AATRIKPKSA-N
in ch i: InChI=1S/C17H17FN2O3/c1-12(20(22)17(19)21)5-6-13-3-2-4-16(11-13)23-15-9-7-14(18)8-10-15/h2-12,22H,1H3,(H2,19,21)/b6-5+
comment: BW B70C is a 5-lipoxygenase (5-LOX) inhibitor.
iupac name: 1-[(E)-4-[3-(4-fluorophenoxy)phenyl]but-3-en-2-yl]-1-hydroxyurea
xref: CHEMBL86676
synonym: BWB70C
synonym: BWB-70C
synonym: BW-B70C
approved: f
ligand name: BW B70C
type: SyntheticOrganicLigand

TYK2 inhibitor 14l
in ch i key: CGDRNYQWTORWBT-UHFFFAOYSA-N
comment: 14l is reported as a selective TYK2 inhibitor <Reference id=41445/>. It was developed to investigate the anti-inflammatory potential of selective TYK2 inhibition.
iupac name: 3-(4-(5-Fluoro-2-((1-((trifluoromethyl)sulfonyl)-1H-indol-5-yl)amino)pyrimidin-4-yl)-1H-pyrazol-1-yl)propanenitrile
approved: f
ligand name: TYK2 inhibitor 14l
type: SyntheticOrganicLigand

CC-90009
in ch i key: PWBHUSLMHZLGRN-UHFFFAOYSA-N
comment: CC-90009 is a clinical stage cereblon E3 ligase modulating drug (CELMoD), that targets the G1 to S phase transition 1 (GSPT1, a.k.a. eRF3A) protein for degradation via the CUL4-DDB1-CRBN-RBX1 (CRL4CRBN) E3 ubiquitin ligase complex <Reference id=41441/>. Binding of CC-90009 to cereblon alters its conformation, and promotes a change in substrate selectivity away from the transcription factors IKZF1/3 and towards to GSPT1. CC-90009-induced depletion of GSPT1 promotes apoptosis of acute myeloid leukemia (AML) cells via activation of the GCN1/GCN2/ATF4 pathway <Reference id=41442/><Reference id=41443/>.
iupac name: 2-(4-chlorophenyl)-N-[[2-(2,6-dioxopiperidin-3-yl)-1-oxo-3H-isoindol-5-yl]methyl]-2,2-difluoroacetamide
synonym: Cereblon modulator 1
synonym: compound 16 [PMID: 33591756]
synonym: Compound 1 [WO2019006299A1]
approved: f
ligand name: CC-90009
type: SyntheticOrganicLigand

PD-146176
canonical SMILES: c1ccc2c(c1)SCc1c2[nH]c2c1cccc2
isomeric SMILES: c1ccc2c(c1)SCc1c2[nH]c2c1cccc2
in ch i key: ZGOOPZVQMLHPFM-UHFFFAOYSA-N
in ch i: InChI=1S/C15H11NS/c1-3-7-13-10(5-1)12-9-17-14-8-4-2-6-11(14)15(12)16-13/h1-8,16H,9H2
comment: PD-146176 is a 15-LOX inhibitor <Reference id=41349/>.
xref: CHEMBL180917
synonym: PD146176
synonym: PD 146176
approved: f
ligand name: PD-146176
type: SyntheticOrganicLigand

SGC6870
in ch i key: NIPTUMFVYBXSMZ-JOCHJYFZSA-N
comment: SGC6870 is a selective inhibitor of protein arginine methyltransferase 6 (PRMT6) <Reference id=41440/>.
iupac name: (5R)-4-(5-bromothiophene-2-carbonyl)-5-(3,5-dimethylphenyl)-7-methyl-3,5-dihydro-1H-1,4-benzodiazepin-2-one
synonym: (R)-2
approved: f
ligand name: SGC6870
type: SyntheticOrganicLigand

sabizabulin
in ch i key: WQGVHOVEXMOLOK-UHFFFAOYSA-N
in ch i: InChI=1S/C21H19N3O4/c1-26-17-8-12(9-18(27-2)20(17)28-3)19(25)16-11-23-21(24-16)14-10-22-15-7-5-4-6-13(14)15/h4-11,22H,1-3H3,(H,23,24)
comment: Sabizabulin (VERU-111) is an orally bioavailable βIII/βIV-tubulin inhibitor that was developed for anti-tumour potential <Reference id=41435/><Reference id=41434/>. It interacts with the tubulin colchicine binding site. VERU-111 induces mitotic arrest and apoptosis in cancer cells in vitro, and inhibits xenograft tumour growth. It is suggested that like colchicine, VERU-111 may have anti-viral and anti-inflammatory actions in addition to its antiproliferative activity. COVID-19: Sabizabulin has been repositioned as a potential therapeutic for COVID-19; in particular for patients who are hospitalised with moderate to severe COVID-19 and who are at high risk for developing acute respiratory distress syndrome (ARDS).
iupac name: [2-(1H-indol-3-yl)-1H-imidazol-5-yl]-(3,4,5-trimethoxyphenyl)methanone
xref: CHEMBL2163631
synonym: VERU-111
synonym: VERU111
approved: f
ligand name: sabizabulin
type: SyntheticOrganicLigand

emvododstat
in ch i key: SRSHBZRURUNOSM-DEOSSOPVSA-N
comment: Emvododstat (PTC299) is an orally bioavailable inhibitor of dihydroorotate dehydrogenase (DHODH) that was developed by PTC Therapeutics <Reference id=41432/> for anti-cancer potential. It inhibits de novo pyrimidine nucleotide (UMP) biosynthesis and exhibits broad activity against leukemia in vitro and in vivo. SARS-CoV-2: Emvododstat inhibits replication of SARS-CoV-2 in vitro (EC50 2.0-31.6 nM) and other RNA viruses <Reference id=41433/>. It blocks production of inflammatory cytokines in infected cell cultures.
iupac name: (4-chlorophenyl) (1S)-6-chloro-1-(4-methoxyphenyl)-1,3,4,9-tetrahydropyrido[3,4-b]indole-2-carboxylate
synonym: PTC-299
synonym: PTC299
approved: f
ligand name: emvododstat
type: SyntheticOrganicLigand

zeteletinib
in ch i key: KOLQINCWMXQEOF-UHFFFAOYSA-N
in ch i: InChI=1S/C25H23F3N4O4/c1-24(2,25(26,27)28)21-11-23(36-32-21)31-22(33)7-14-5-6-17(29-12-14)16-8-15-9-19(34-3)20(35-4)10-18(15)30-13-16/h5-6,8-13H,7H2,1-4H3,(H,31,33)
comment: This entry was generated from the chemical structure for the INN zeteletinib, which resolved via PubChem and SureChEMBL to Daiichi Sankyo patent WO2018060714A1 <Reference id=41412/>. The compounds in this patent are claimed as RET kinase inhibitors, principally for the treatment of proliferative diseases. The zeteletinib structure is claimed as Example 3. In the absence of formal name>structure disclosure we have been unable to determine the clinical development stage of this compound.
iupac name: 2-[6-(6,7-dimethoxyquinolin-3-yl)pyridin-3-yl]-N-[3-(1,1,1-trifluoro-2-methylpropan-2-yl)-1,2-oxazol-5-yl]acetamide
synonym: Example 3 [WO2018060714A1]
synonym: BOS172738
synonym: BOS-172738
synonym: DS-5010
synonym: DS5010
approved: f
ligand name: zeteletinib
type: SyntheticOrganicLigand

zabedosertib
in ch i key: OQAMEEFUUFJZRS-UHFFFAOYSA-N
comment: This entry was generated using the chemical structure for the INN zabedosertib. This resolved via PubChem to Example 12 in Bayer's patent WO2016083433A1 <Reference id=41411/>. From this patent zabedosertib appears to be an IRAK4 inhibitor, that was claimed for immunomodulatory potential.
iupac name: N-[6-(2-hydroxypropan-2-yl)-2-(2-methylsulfonylethyl)indazol-5-yl]-6-(trifluoromethyl)pyridine-2-carboxamide
synonym: BAY1834845
synonym: BAY-1834845
approved: f
ligand name: zabedosertib
type: SyntheticOrganicLigand

tasurgratinib
in ch i key: IBHOLSBDZMIPPT-UHFFFAOYSA-N
in ch i: InChI=1S/C32H37N5O6/c1-33-32(40)37-14-10-25-19-29(28(21-27(25)37)42-18-17-41-2)43-26-7-11-34-30(20-26)35-31(39)24-5-3-22(4-6-24)23-8-12-36(13-9-23)15-16-38/h3-7,10-11,14,19-21,23,38H,8-9,12-13,15-18H2,1-2H3,(H,33,40)(H,34,35,39)
comment: The chemical structure for the INN tasurgratinib resolves to E-7090 via PubChem, and is claimed as Example 22 in patent WO2014129477A1 as an inhibitor of FGFR pathway signalling <Reference id=41410/>.
iupac name: 5-[2-[[4-[1-(2-hydroxyethyl)piperidin-4-yl]benzoyl]amino]pyridin-4-yl]oxy-6-(2-methoxyethoxy)-N-methylindole-1-carboxamide
xref: CHEMBL3686884
synonym: E-7090
synonym: E7090
synonym: Example 22 [WO2014129477A1]
approved: f
ligand name: tasurgratinib
type: SyntheticOrganicLigand

nemtabrutinib
in ch i key: JSFCZQSJQXFJDS-QAPCUYQASA-N
in ch i: InChI=1S/C25H23ClN4O4/c26-21-10-17(34-16-4-2-1-3-5-16)8-9-19(21)23(32)20-11-27-24-22(20)25(29-14-28-24)30-15-6-7-18(12-31)33-13-15/h1-5,8-11,14-15,18,31H,6-7,12-13H2,(H2,27,28,29,30)/t15-,18+/m1/s1
comment: Nemtabrutinib (ARQ-531) is a reversible, ATP-competitive kinase inhibitor, that was originally designed to inhibit Bruton tyrosine kinase (BTK) <Reference id=41408/>. It does not interact with BTK's catalytic domain Cys481 so may not be susceptible to resistance conferred by mutation of this residue. This is in contrast to ibrutinib, which is sensitive to alterations at Cys481. Nemtabrutinib has inhibitory activities against a range of other TEC family kinases, as well as Src and Trk kinases <Reference id=41408/><Reference id=41409/>. This non-selective activity is believed to contribute to nemtabrutinib's efficacy against chronic lymphocytic leukemia cells.
iupac name: (2-chloro-4-phenoxyphenyl)-[4-[[(3R,6S)-6-(hydroxymethyl)oxan-3-yl]amino]-7H-pyrrolo[2,3-d]pyrimidin-5-yl]methanone
synonym: ARQ-531
synonym: ARQ531
synonym: MK-1026
synonym: MK1026
synonym: ArQule 531
approved: f
ligand name: nemtabrutinib
type: SyntheticOrganicLigand

elraglusib
in ch i key: FARXPFGGGGLENU-UHFFFAOYSA-N
in ch i: InChI=1S/C22H13FN2O5/c1-25-7-13(11-5-17-18(6-15(11)25)30-9-29-17)19-20(22(27)24-21(19)26)14-8-28-16-3-2-10(23)4-12(14)16/h2-8H,9H2,1H3,(H,24,26,27)
comment: This entry was generated using the chemical structure that was submitted to the WHO for INN elraglusib. In that submission it is described as a glycogen synthase kinase inhibitor. The chemical structure also matches that of 9-ING-41 <Reference id=41407/> which is a maleimide-based GSK-3 inhibitor <Reference id=41393/> and an oncology clinical lead.
iupac name: 3-(5-fluoro-1-benzofuran-3-yl)-4-(5-methyl-[1,3]dioxolo[4,5-f]indol-7-yl)pyrrole-2,5-dione
xref: CHEMBL483465
synonym: 9-ING-41
synonym: compound 26 [PMID: 19338355]
approved: f
ligand name: elraglusib
type: SyntheticOrganicLigand

edaxeterkib
in ch i key: SQNCXVDXNAUREB-HXUWFJFHSA-N
in ch i: InChI=1S/C26H27N7O2/c1-35-25-27-12-19(13-28-25)24-21-10-18-15-33(26(34)29-22(18)11-23(21)30-31-24)20-8-5-9-32(16-20)14-17-6-3-2-4-7-17/h2-4,6-7,10-13,20H,5,8-9,14-16H2,1H3,(H,29,34)(H,30,31)/t20-/m1/s1
comment: This entry shows the chemical structure that was submitted to the WHO for the INN edaxeterkib, which is described as a tyrosine kinase inhibitor and antineoplastic. This same chemical structure is claimed in Kura Oncology's patent WO2015051341A1 as an ERK inhibitor (with prior art in WO2015051341A1, Araxes Pharma).
synonym: Example 104 [WO2015051341A1]
approved: f
ligand name: edaxeterkib
type: SyntheticOrganicLigand

deuruxolitinib
in ch i key: HFNKQEVNSGCOJV-FBXGHSCESA-N
in ch i: InChI=1S/C17H18N6/c18-7-5-15(12-3-1-2-4-12)23-10-13(9-22-23)16-14-6-8-19-17(14)21-11-20-16/h6,8-12,15H,1-5H2,(H,19,20,21)/t15-/m1/s1/i1D2,2D2,3D2,4D2
comment: Deuruxolitinib (CTP-543) is a deuterium-modified analogue of the JAK inhibitor <Ligand id=5688/>. It is an oral inhibitor that inhibits JAK1/2. The chemical structure, and its use in hair loss disorders are claimed in patent WO2017192905A1 <Reference id=41399/>.
iupac name: (3R)-3-(2,2,3,3,4,4,5,5-octadeuteriocyclopentyl)-3-[4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propanenitrile
synonym: CTP-543
synonym: CTP543
synonym: D8-ruxolitinib
approved: f
ligand name: deuruxolitinib
type: SyntheticOrganicLigand

cimpuciclib
in ch i key: FDSYOFCVZBGPOV-UHFFFAOYSA-N
in ch i: InChI=1S/C30H35FN8O/c1-17(2)39-19(4)34-25-9-5-20(15-26(25)39)28-24(31)16-32-30(37-28)36-27-10-8-23(18(3)33-27)29(40)38-13-11-22(12-14-38)35-21-6-7-21/h5,8-10,15-17,21-22,35H,6-7,11-14H2,1-4H3,(H,32,33,36,37)
comment: The chemical structure that was submitted to the WHO for the INN cimpuciclib, matches the stucture of example 63 that is claimed in patent WO2018045956A1 <Reference id=41397/>. Data is provided in WO2018045956A1 for example 63's inhibitory activity at CDK4 and CDK6, and for antiproliferative activity against Colo205 colon cancer cells in vitro (IC50 141 nM) and Colo205 xenografts in nude mice.
synonym: example 63 [WO2018045956A1]
approved: f
ligand name: cimpuciclib
type: SyntheticOrganicLigand

compound 4 [PMID: 33531496]
in ch i key: XUMZHCJVSWBFGZ-UHFFFAOYSA-N
in ch i: InChI=1S/C18H13F3N2O/c19-18(20,21)13-8-12(9-14(22)10-13)17(24)23-16-7-3-5-11-4-1-2-6-15(11)16/h1-10H,22H2,(H,23,24)
comment: Compound 4 is reported as an inhibitor of SARS-CoV-2 papain-like protease (PL-pro) <Reference id=41394/>. It has relatively low potency against the enzyme in a cell-free assay, but is one of the most potent inhibitors of in vitro viral replication in the study.
iupac name: 3-amino-N-(naphthalen-1-yl)-5-(trifluoromethyl)benzamide
approved: f
ligand name: compound 4 [PMID: 33531496]
type: SyntheticOrganicLigand

T5-8
canonical SMILES: O=C1C(=O)c2cccnc2c2c1cccn2
isomeric SMILES: O=C1C(=O)c2cccnc2c2c1cccn2
in ch i key: KCALAFIVPCAXJI-UHFFFAOYSA-N
in ch i: InChI=1S/C12H6N2O2/c15-11-7-3-1-5-13-9(7)10-8(12(11)16)4-2-6-14-10/h1-6H
comment: T5-8 has been reported as an agonist of the bitter taste receptor TAS2R5 <Reference id=40957/>. It has been proposed as a novel bronchodilator that acts via agonism of TAS2R5 expressed in airway smooth muscle cells.
iupac name: 1,10-phenanthroline-5,6-dione
xref: CHEMBL235504
approved: f
ligand name: T5-8
type: SyntheticOrganicLigand

compound 5 [PMID: 19338355]
in ch i key: JBKILIGSDAQHSL-UHFFFAOYSA-N
in ch i: InChI=1S/C22H14FIN2O4/c1-26-8-12(11-6-14(23)15(24)7-16(11)26)18-19(22(28)25-21(18)27)13-9-30-20-10(13)4-3-5-17(20)29-2/h3-9H,1-2H3,(H,25,27,28)
comment: Compound 5 is a glycogen synthase kinase 3β inhibitor <Reference id=41393/>. It suppresses growth of pancreatic cancer cells in vitro.
iupac name: 3-(5-Fluoro-6-iodo-1-methyl-1H-indol-3-yl)-4-(7-methoxybenzofuran-3-yl)pyrrole-2,5-dione
xref: CHEMBL523435
approved: f
ligand name: compound 5 [PMID: 19338355]
type: SyntheticOrganicLigand

zaloglanstat
in ch i key: DOVBVLUPCQSAGE-UHFFFAOYSA-N
comment: The chemical structure that was submitted for the INN zaloglanstat (described as a prostaglandin synthase inhibitor) is claimed in Glenmark Pharmaceuticals' patent WO2013186692A1 as Example 100 <Reference id=41391/>. The patent claims the compound as a microsomal prostaglandin E synthase-1 (mPGES-1) inhibitor for application in chronic inflammatory conditions. Online investigation (including Glenmark's US pipeline webpage) suggests that zaloglanstat could be Glenmark's lead, GRC 27864/ISC 27864 (a potent, selective, and orally bioavailable inhibitor), which has completed first-in-human evaluation in healthy trial participants <Reference id=41392/>.
iupac name: N-[(4-chloro-3-{5-oxo-1-[4-(trifluoromethyl)phenyl]-2,5-dihydro-1H-1,2,4-triazol-3-yl}phenyl)methyl]-2,2-dimethylpropanamide
approved: f
ligand name: zaloglanstat
type: SyntheticOrganicLigand

LP533401
in ch i key: JZWUKILTKYJLCN-XEGCMXMBSA-N
in ch i: InChI=1S/C27H22F4N4O3/c28-20-3-1-2-19(13-20)16-8-10-18(11-9-16)24(27(29,30)31)38-23-14-22(34-26(33)35-23)17-6-4-15(5-7-17)12-21(32)25(36)37/h1-11,13-14,21,24H,12,32H2,(H,36,37)(H2,33,34,35)/t21-,24?/m0/s1
comment: LP533401 is a peripherally active inhibitor of L-Trytophan hydroxylase 1 (TPH1) that was designed by Lexicon Pharmaceuticals <Reference id=41389/>.
iupac name: (2S)-2-amino-3-[4-[2-amino-6-[2,2,2-trifluoro-1-[4-(3-fluorophenyl)phenyl]ethoxy]pyrimidin-4-yl]phenyl]propanoic acid
xref: CHEMBL511275
synonym: LP-533401
approved: f
ligand name: LP533401
type: SyntheticOrganicLigand

compound 23a [PMID: 33417443]
in ch i key: DAAXYQZSKBPJOX-FQEVSTJZSA-N
in ch i: InChI=1S/C24H21N3O5/c1-31-21-11-8-17(13-19(21)15-6-9-18(28)10-7-15)23-26-22(27-32-23)16-4-2-14(3-5-16)12-20(25)24(29)30/h2-11,13,20,28H,12,25H2,1H3,(H,29,30)/t20-/m0/s1
comment: Compound 23a is reported as an inhibitor of L-Tryptophan hydroxylase 1 (TPH1) <Reference id=41388/>. It shows peripherally restricted distribution in vivo. Agents with this mechanism of action are known to selectively deplete serotonin in the gastrointestinal tract, and are being investigated for potential as a therapeutic approach for the treatment of obesity and fatty liver diseases.
iupac name: (S)-2-amino-3-(4-(5-(4′-hydroxy-6-methoxy-[1,1′-biphenyl]-3-yl)-1,2,4-oxadiazol-3-yl)phenyl)propanoic acid
approved: f
ligand name: compound 23a [PMID: 33417443]
type: SyntheticOrganicLigand

JH112
in ch i key: CRLKYMWQHWKXAE-FDDCHVKYSA-N
in ch i: InChI=1S/C26H29ClN6O2/c1-4-18(3)23-16-31(26-30-21-15-19(27)7-9-24(21)35-26)12-5-13-32(23)25(34)20-14-17(2)6-8-22(20)33-28-10-11-29-33/h6-11,14-15,18,23H,4-5,12-13,16H2,1-3H3/t18-,23+/m0/s1
comment: JH112 is an orexin receptor antagonist <Reference id=41386/>. It is 75-fold selective for OX1 over OX2.
iupac name: [(2S)-2-[(2S)-butan-2-yl]-4-(5-chloro-1,3-benzoxazol-2-yl)-1,4-diazepan-1-yl]-[5-methyl-2-(triazol-2-yl)phenyl]methanone
synonym: compound 2 [PMID: 32669442]
approved: f
ligand name: JH112
type: SyntheticOrganicLigand

acivicin
canonical SMILES: N[C@H](C(=O)O)[C@@H]1CC(=NO1)Cl
isomeric SMILES: N[C@H](C(=O)O)[C@@H]1CC(=NO1)Cl
in ch i key: QAWIHIJWNYOLBE-OKKQSCSOSA-N
in ch i: InChI=1S/C5H7ClN2O3/c6-3-1-2(11-8-3)4(7)5(9)10/h2,4H,1,7H2,(H,9,10)/t2-,4-/m0/s1
comment: Acivicin is a structural analogue of glutamine and antimetabolite type antineoplastic agent, that inhibits several glutamate-dependent synthetic enzymes and glutamate metabolism. It also has antimicrobial and antileishmanial activities.
iupac name: (2S)-2-amino-2-[(5S)-3-chloro-4,5-dihydro-1,2-oxazol-5-yl]acetic acid
xref: CHEMBL1231101
synonym: AT125
synonym: U 42,126
synonym: AT-125
synonym: U-42,126
synonym: U-42126
approved: f
ligand name: acivicin
type: SyntheticOrganicLigand

BJP-06-005-3
in ch i key: SUAZSPTYLUTEDZ-ORYMTKCHSA-N
in ch i: InChI=1S/C37H48ClN7O7/c1-3-52-36(50)28(16-11-18-40-37(39)51)42-33(47)29(21-25-23-41-27-15-8-7-14-26(25)27)43-34(48)30-17-9-10-19-45(30)35(49)31(44(2)32(46)22-38)20-24-12-5-4-6-13-24/h4-8,12-15,23,28-31,41H,3,9-11,16-22H2,1-2H3,(H,42,47)(H,43,48)(H3,39,40,51)/t28-,29-,30-,31-/m0/s1
comment: BJP-06-005-3 is a peptide-based inhibitor of peptidylprolyl cis/trans isomerase, NIMA-interacting 1 (PIN1) <Reference id=41377/>. It is a covalent inhibitor that targets the conserved Cys113 residue within the PiIN1 active site. BJP-06-005-3 is active in cellular assays, and offers a tool compound that is suitable for investigating PIN1 biology and its role in cancer.
iupac name: ethyl (2S)-5-(carbamoylamino)-2-[[(2S)-2-[[(2S)-1-[(2S)-2-[(2-chloroacetyl)-methylamino]-3-phenylpropanoyl]piperidine-2-carbonyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]pentanoate
synonym: compound 1 [PMID: 32483379]
synonym: N-(chloroacetyl)-N-methyl-L-phenylalanyl-L-homoprolyl-L-tryptophyl-L-citrulline ethyl ester
approved: f
ligand name: BJP-06-005-3
type: PeptideLigand

AG-17724
in ch i key: NKMPZFCFXCJBEY-GOSISDBHSA-N
in ch i: InChI=1S/C21H16FN3O3/c22-15-7-8-16-17(10-15)24-19(23-16)11-18(21(27)28)25-20(26)14-6-5-12-3-1-2-4-13(12)9-14/h1-10,18H,11H2,(H,23,24)(H,25,26)(H,27,28)/t18-/m1/s1
comment: AG-17724 is an experimental inhibitor of the catalytic activity of PPIase PIN1 (peptidylprolyl cis/trans isomerase, NIMA-interacting 1) in biochemical assay <Reference id=41370/>. It has limited solubility and little activity in cellular assays. <Ligand id=11399/> from the same study has improved solubility, retains inhibition potency and is active in a cell-based proliferation assay.
iupac name: (2R)-3-(6-fluoro-1H-benzimidazol-2-yl)-2-(naphthalene-2-carbonylamino)propanoic acid
xref: CHEMBL3322219
synonym: compound 7 [PMID: 25091930]
synonym: AG17724
approved: f
ligand name: AG-17724
type: SyntheticOrganicLigand

compound 20 [PMID: 25091930]
in ch i key: FHXPZYVYXRJXQI-UHFFFAOYSA-N
comment: Compound 20 was discovered in the same SAR study as <Ligand id=11398/>. It has slightly lower inhibitory effect on PIN1 than AG-122018, but has improved activity in whole cell assays.<Reference id=41370/>.
iupac name: 2-[2-(2,6-dichlorophenyl)ethyl]-4-[(6-fluoro-1H-indol-2-yl)methyl]-5H-1,3-thiazole-4-carboxylic acid
xref: CHEMBL3322230
approved: f
ligand name: compound 20 [PMID: 25091930]
type: SyntheticOrganicLigand

AG-122018
in ch i key: ZWSNYKPAUKAJCT-XMMPIXPASA-N
in ch i: InChI=1S/C26H21FN2O3/c27-16-10-9-15-11-17(28-23(15)12-16)13-24(26(31)32)29-25(30)14-22-20-7-3-1-5-18(20)19-6-2-4-8-21(19)22/h1-12,22,24,28H,13-14H2,(H,29,30)(H,31,32)/t24-/m1/s1
comment: AG-122018 is an inhibitor of the peptidyl-prolyl isomerase (PPIase) PIN1 <Reference id=41370/>. It is a small molecule that targets the phosphate binding site of the enzyme, and has been designed with a carboxylate replacing the phosphate group. However, this compound is inactive in whole cells assays.
iupac name: (2R)-2-[[2-(9H-fluoren-9-yl)acetyl]amino]-3-(6-fluoro-1H-indol-2-yl)propanoic acid
xref: CHEMBL3353369
synonym: compound 18 [PMID: 25091930]
approved: f
ligand name: AG-122018
type: SyntheticOrganicLigand

compound 40 [PMID: 33470814]
canonical SMILES: COc1cc(cc2c1n(C/C=C/Cn1/c(=N/C(=O)c3cc(nn3CC)C)/[nH]c3c1c(OCCCN1CCOCC1)cc(c3)C(=O)N)/c(=N/C(=O)c1cc(nn1CC)C)/[nH]2)c1ncn[nH]1
isomeric SMILES: COc1cc(cc2c1n(C/C=C/Cn1/c(=N/C(=O)c3cc(nn3CC)C)/[nH]c3c1c(OCCCN1CCOCC1)cc(c3)C(=O)N)/c(=N/C(=O)c1cc(nn1CC)C)/[nH]2)c1ncn[nH]1
in ch i key: RZBQZKAZIZWIRZ-CMDGGOBGSA-N
in ch i: InChI=1S/C43H51N15O6/c1-6-57-32(19-26(3)52-57)40(60)49-42-48-31-22-29(39-45-25-46-51-39)24-34(62-5)36(31)55(42)12-8-9-13-56-37-30(47-43(56)50-41(61)33-20-27(4)53-58(33)7-2)21-28(38(44)59)23-35(37)64-16-10-11-54-14-17-63-18-15-54/h8-9,19-25H,6-7,10-18H2,1-5H3,(H2,44,59)(H,45,46,51)(H,47,50,61)(H,48,49,60)/b9-8+
comment: Compound 40 is a non-cyclic dinucleotide agonist of stimulator of interferon gene (STING) pathway <Reference id=41362/>. It was developed for immuno-oncology potential. In vitro, compound 40 has been shown to bind directly to all human STING isoforms tested, and to mouse STING.
iupac name: (E)-2-((1-Ethyl-3-methyl-1H-pyrazole-5-carbonyl)imino)-1-((E)-4-((E)-2-((1-ethyl-3-methyl-1H-pyrazole-5-carbonyl)imino)-7-methoxy-5-(1H-1,2,4-triazol-5-yl)-2,3-dihydro-1H-benzo[d]imidazol-1-yl)but-2-en-1-yl)-7-(3-morpholinopropoxy)-2,3-dihydro-1H-benzo[d]imidazole-5-carboxamide
approved: f
ligand name: compound 40 [PMID: 33470814]
type: SyntheticOrganicLigand

plitidepsin
in ch i key: UUSZLLQJYRSZIS-LXNNNBEUSA-N
in ch i: InChI=1S/C57H87N7O15/c1-15-33(8)46-44(66)29-45(67)79-49(32(6)7)48(68)34(9)50(69)58-39(26-30(2)3)54(73)64-25-17-19-41(64)56(75)62(13)43(28-37-20-22-38(77-14)23-21-37)57(76)78-36(11)47(52(71)59-46)60-51(70)42(27-31(4)5)61(12)55(74)40-18-16-24-63(40)53(72)35(10)65/h20-23,30-34,36,39-44,46-47,49,66H,15-19,24-29H2,1-14H3,(H,58,69)(H,59,71)(H,60,70)/t33-,34-,36+,39-,40-,41-,42+,43-,44-,46+,47-,49-/m0/s1
comment: Plitidepsin was isolated from the sea squirt Aplidium albicans. It was found to have potent anti-tumour activity, that is mediated via modulation of human elongation factor 1-α (eEF1A) proteins and the translation process. Plitidepsin is also an immunomodulator and has antiviral properties. SARS-CoV-2: The coronavirus exploits the eukaryotic (host) translation machinery to allow it to replicate. As a translation disruptor, plitidepsin has demonstrated in vivo anti-SARS-CoV-2 activity in mouse models of infection <Reference id=41358/>. Under in vitro experimental conditions plitidepsin inhibited SARS-CoV-2 replication more effectively than <Ligand id=10715/>.
synonym: Dehydrodidemnin B
synonym: Aplidin®
synonym: aplidine
approved: t
ligand name: plitidepsin
type: NaturalProductLigand

TFC007
in ch i key: NLSSUSRERAMBTA-UHFFFAOYSA-N
in ch i: InChI=1S/C27H29N5O4/c33-25(21-18-28-27(29-19-21)36-24-4-2-1-3-5-24)30-22-6-8-23(9-7-22)31-12-10-20(11-13-31)26(34)32-14-16-35-17-15-32/h1-9,18-20H,10-17H2,(H,30,33)
comment: TCD007 is an inhibitor of hematopoietic prostaglandin D synthase <Reference id=41346/>.
iupac name: N-[4-[4-(morpholine-4-carbonyl)piperidin-1-yl]phenyl]-2-phenoxypyrimidine-5-carboxamide
xref: CHEMBL4238186
synonym: TFC 007
synonym: TFC-007
approved: f
ligand name: TFC007
type: SyntheticOrganicLigand

SC-58125
in ch i key: JHBIMJKLBUMNAU-UHFFFAOYSA-N
comment: SC-58125 is a selective cyclooxygenase-2 (COX-2) inhibitor <Reference id=41344/>.
iupac name: 5-(4-fluorophenyl)-1-(4-methylsulfonylphenyl)-3-(trifluoromethyl)pyrazole
xref: CHEMBL274990
synonym: SC 58125
synonym: SC58125
approved: f
ligand name: SC-58125
type: SyntheticOrganicLigand

dotinurad
in ch i key: VOFLAIHEELWYGO-UHFFFAOYSA-N
in ch i: InChI=1S/C14H9Cl2NO4S/c15-9-5-8(6-10(16)13(9)18)14(19)17-7-22(20,21)12-4-2-1-3-11(12)17/h1-6,18H,7H2
comment: Dotinurad, a novel selective urate reabsorption inhibitor (SURI), that acts on the URAT-1 transporter.
synonym: Urece®
synonym: FYU-981
synonym: FYU981
approved: t
ligand name: dotinurad
type: SyntheticOrganicLigand

voclosporin
in ch i key: BICRTLVBTLFLRD-PTWUADNWSA-N
comment: Voclosporin (ISA247, ISATX247) is a cyclic peptide that is a semi-synthetic cyclosporine analogue <Reference id=41336/><Reference id=41335/><Reference id=41334/><Reference id=41332/>, but with distinct clinical efficacy and safety profiles <Reference id=41331/>. Like cyclosporine, it has immunosuppressive action, and it binds cyclophilin A <Reference id=41333/>. Functionally, it acts as a calcineurin inhibitor. Prior to voclosporin, clinically used calcineurin inhibitors were cyclosporine (<Ligand id=1024/>), <Ligand id=6784/>, and <Ligand id=6783/>.
iupac name: (3S,6S,9S,12R,15S,18S,21S,24S,30S,33S)-30-ethyl-33-[(1R,2R,4E)-1-hydroxy-2-methylhepta-4,6-dienyl]-1,4,7,10,12,15,19,25,28-nonamethyl-6,9,18,24-tetrakis(2-methylpropyl)-3,21-di(propan-2-yl)-1,4,7,10,13,16,19,22,25,28,31-undecazacyclotritriacontane-2,5,8,11,14,17,20,23,26,29,32-undecone
synonym: 1,11-anhydro[L-alanyl-D-alanyl-N-methyl-L-leucyl-N-methyl-L-leucyl- N-methyl-L-valyl-[(2S,3R,4R,6E)-3-hydroxy-4-methyl- 2-(methylamino)nona-6,8-dienoyl][(2S)-2-aminobutanoyl]- N-methylglycyl-N-methyl-L-leucyl-L-valyl-N-methyl-L-leucine]
synonym: ISA-247
synonym: ISATX247
synonym: ISA247
synonym: Lupkynis®
synonym: E-ISA247
synonym: ISA(TX)247
synonym: R 1524
synonym: R1524
synonym: R-1524
approved: t
ligand name: voclosporin
type: PeptideLigand

rilpivirine
canonical SMILES: N#C/C=C/c1cc(C)c(c(c1)C)Nc1ccnc(n1)Nc1ccc(cc1)C#N
isomeric SMILES: N#C/C=C/c1cc(C)c(c(c1)C)Nc1ccnc(n1)Nc1ccc(cc1)C#N
in ch i key: YIBOMRUWOWDFLG-ONEGZZNKSA-N
in ch i: InChI=1S/C22H18N6/c1-15-12-18(4-3-10-23)13-16(2)21(15)27-20-9-11-25-22(28-20)26-19-7-5-17(14-24)6-8-19/h3-9,11-13H,1-2H3,(H2,25,26,27,28)/b4-3+
comment: Rilpivirine is an oral non-nucleoside reverse transcriptase inhibitor (NNRTI) HIV medication.
xref: CHEMBL175691
synonym: TMC-278
synonym: TMC278
synonym: Edurant®
approved: t
ligand name: rilpivirine
type: SyntheticOrganicLigand

cabotegravir
in ch i key: WCWSTNLSLKSJPK-LKFCYVNXSA-N
comment: Cabotegravir (GSK1265744, CAB) is a long-acting HIV integrase inhibitor. It is structurally related to <Ligand id=7365/>.
xref: CHEMBL2403238
synonym: GSK1265744
synonym: GSK-1265744
synonym: GSK744
synonym: CAB
synonym: Cabenuva® (cabotegravir + rilpivirine)
synonym: Vocabria®
approved: t
ligand name: cabotegravir
type: SyntheticOrganicLigand

4OH-GTS-21
canonical SMILES: COc1cc(O)ccc1/C=C/1/CCCN=C1c1cccnc1
isomeric SMILES: COc1cc(O)ccc1/C=C/1/CCCN=C1c1cccnc1
in ch i key: KXAAIPFSUGPVMQ-GXDHUFHOSA-N
in ch i: InChI=1S/C18H18N2O2/c1-22-17-11-16(21)7-6-13(17)10-14-4-3-9-20-18(14)15-5-2-8-19-12-15/h2,5-8,10-12,21H,3-4,9H2,1H3/b14-10+
comment: 4OH-GTS-21 is an anlaogue of <Ligand id=11384/> <Reference id=41322/>. Like the parent molecule is acts as an agonist at the α7 nicotinic acetylcholine receptor (a ligand-gated ion channel).
iupac name: 3-methoxy-4-[(E)-(6-pyridin-3-yl-3,4-dihydro-2H-pyridin-5-ylidene)methyl]phenol
xref: CHEMBL1162395
synonym: 4-OH-MBA
synonym: 4-OH-GTS-21
approved: f
ligand name: 4OH-GTS-21
type: SyntheticOrganicLigand

GTS-21
canonical SMILES: COc1cc(OC)ccc1/C=C/1/CCCN=C1c1cccnc1
isomeric SMILES: COc1cc(OC)ccc1/C=C/1/CCCN=C1c1cccnc1
in ch i key: RPYWXZCFYPVCNQ-RVDMUPIBSA-N
in ch i: InChI=1S/C19H20N2O2/c1-22-17-8-7-14(18(12-17)23-2)11-15-5-4-10-21-19(15)16-6-3-9-20-13-16/h3,6-9,11-13H,4-5,10H2,1-2H3/b15-11+
comment: GTS-21 (DMBX-A), is a novel, small-molecule, orally active and selective α7 nicotinic acetylcholine (nACh) receptor agonist, that has been advanced to clinical evaluation in a range of conditions <Reference id=41317/>. There is a report that the anti-inflammatory effects of GTS-21 may be in part due to α7 nACh receptor-independent activity <Reference id=41319/>.
iupac name: 3-[(5E)-5-[(2,4-dimethoxyphenyl)methylidene]-3,4-dihydro-2H-pyridin-6-yl]pyridine
xref: CHEMBL134713
synonym: DMBX-A
approved: f
ligand name: GTS-21
type: SyntheticOrganicLigand

NS6740
in ch i key: VSOWCIMCDKXVRC-UHFFFAOYSA-N
in ch i: InChI=1S/C19H19F3N2O2/c20-19(21,22)14-3-1-2-13(12-14)16-4-5-17(26-16)18(25)24-11-10-23-8-6-15(24)7-9-23/h1-5,12,15H,6-11H2
comment: NS6740 (A-582941) is described as a silent agonist (or metagonist) of α7 nicotinic acetylcholine receptors (CHRNA7; nAChR, a ligand-gated ion channel) <Reference id=41315/>. This means that it binds to the receptor but has no intrinsic agonist activity (and may induce conformational change to a non-conducting state), but it does increase receptor sensitivity to positive allosteric modulators (PAMs). The α7 nAChR; is a promising drug target inflammatory diseases and neurological disorders (e.g. chronic and neuropathic) pain. NS6740 can be used to explore the most suitable mechanistic approach by which to achive clinical benefit from modulating the α7 nAChR <Reference id=41316/>.
iupac name: 1,4-diazabicyclo[3.2.2]nonan-4-yl-[5-[3-(trifluoromethyl)phenyl]furan-2-yl]methanone
xref: CHEMBL2380804
synonym: A-793394
synonym: NS-6740
synonym: A793394
approved: f
ligand name: NS6740
type: SyntheticOrganicLigand

lunacalcipol
canonical SMILES: O[C@H]1C[C@H](O)C(=C)/C(=C/C=C/2/CCC[C@]3([C@H]2CC=C3[C@@H](C/C=C/S(=O)(=O)C(C)(C)C)C)C)/C1
isomeric SMILES: O[C@H]1C[C@H](O)C(=C)/C(=C/C=C/2/CCC[C@]3([C@H]2CC=C3[C@@H](C/C=C/S(=O)(=O)C(C)(C)C)C)C)/C1
in ch i key: RFQHCLMGLJGZNV-UXXOMSPDSA-N
in ch i: InChI=1S/C28H42O4S/c1-19(9-8-16-33(31,32)27(3,4)5)24-13-14-25-21(10-7-15-28(24,25)6)11-12-22-17-23(29)18-26(30)20(22)2/h8,11-13,16,19,23,25-26,29-30H,2,7,9-10,14-15,17-18H2,1,3-6H3/b16-8+,21-11+,22-12-/t19-,23-,25+,26+,28-/m1/s1
comment: Lunacalcipol (CTA018) is a vitamin D analogue.
iupac name: (1R,3S,5Z)-5-[(2E)-2-[(3aS,7aS)-1-[(E,2R)-5-tert-butylsulfonylpent-4-en-2-yl]-7a-methyl-3a,5,6,7-tetrahydro-3H-inden-4-ylidene]ethylidene]-4-methylidenecyclohexane-1,3-diol
xref: CHEMBL2105705
synonym: CTA018
synonym: CTA018/MT2832
synonym: CTA-018
approved: f
ligand name: lunacalcipol
type: SyntheticOrganicLigand

talarozole
in ch i key: SNFYYXUGUBUECJ-UHFFFAOYSA-N
in ch i: InChI=1S/C21H23N5S/c1-3-15(4-2)20(26-14-22-13-23-26)16-9-11-17(12-10-16)24-21-25-18-7-5-6-8-19(18)27-21/h5-15,20H,3-4H2,1-2H3,(H,24,25)
comment: Talarozole (R115866) is a cytochrome P450 CYP26 inhibitor. It was investigated for clinical efficacy as a treatment for cutaneous inflammation, including psoriasis.
iupac name: N-[4-[2-ethyl-1-(1,2,4-triazol-1-yl)butyl]phenyl]-1,3-benzothiazol-2-amine
xref: CHEMBL459505
synonym: Rambazole®
synonym: R115866
synonym: R-115866
approved: f
ligand name: talarozole
type: SyntheticOrganicLigand

R116010
in ch i key: WGVPSTQRQHGEEP-MGPUTAFESA-N
in ch i: InChI=1S/C21H23N5S/c1-15(25(2)3)20(26-13-12-22-14-26)16-8-10-17(11-9-16)23-21-24-18-6-4-5-7-19(18)27-21/h4-15,20H,1-3H3,(H,23,24)/t15-,20+/m0/s1
comment: R116010 is a CYP26A1 inhibitor <Reference id=41311/>. It inhibits metabolism of all-trans-retinoic acid.
iupac name: N-[4-[(1S,2S)-2-(dimethylamino)-1-imidazol-1-ylpropyl]phenyl]-1,3-benzothiazol-2-amine
synonym: NIL6PST6V7
approved: f
ligand name: R116010
type: SyntheticOrganicLigand

picotamide
in ch i key: KYWCWBXGRWWINE-UHFFFAOYSA-N
in ch i: InChI=1S/C21H20N4O3/c1-28-19-7-6-17(20(26)24-13-15-4-2-8-22-11-15)10-18(19)21(27)25-14-16-5-3-9-23-12-16/h2-12H,13-14H2,1H3,(H,24,26)(H,25,27)
comment: Picotamide is a thromboxane synthase inhibitor. It inhibits platelet aggregation.
iupac name: 4-methoxy-1-N,3-N-bis(pyridin-3-ylmethyl)benzene-1,3-dicarboxamide
xref: CHEMBL1257015
approved: f
ligand name: picotamide
type: SyntheticOrganicLigand

furegrelate sodium
canonical SMILES: [O-]C(=O)c1oc2c(c1)cc(cc2)Cc1cccnc1.[Na+]
isomeric SMILES: [O-]C(=O)c1oc2c(c1)cc(cc2)Cc1cccnc1.[Na+]
in ch i key: XBTIPIZROJAKOJ-UHFFFAOYSA-M
in ch i: InChI=1S/C15H11NO3.Na/c17-15(18)14-8-12-7-10(3-4-13(12)19-14)6-11-2-1-5-16-9-11;/h1-5,7-9H,6H2,(H,17,18);/q;+1/p-1
comment: Furegrelate is a potent inhibitor of thromboxane synthase. It has minimal effect on other arachidonate metabolic enzymes.
iupac name: sodium;5-(pyridin-3-ylmethyl)-1-benzofuran-2-carboxylate
xref: CHEMBL36028
synonym: U-63557A
synonym: U63557A
approved: f
ligand name: furegrelate sodium
type: SyntheticOrganicLigand

troriluzole
in ch i key: YBZSGIWIPOUSHY-UHFFFAOYSA-N
comment: Troriluzole (BHV-4157) is a prodrug of the voltage-dependent calcium channel blocker riluzole. Chemically it is riluzole conjugated to a tripeptide carrier (IUPAC sequence H-Gly-Gly-Sar-Unk, where Unk = the riluzole component), and the active moiety is released by peptidases in vivo. The prodrug is more stable than riluzole and is suitable for once-daily dosing.
xref: CHEMBL4297586
synonym: BHV-4157
synonym: BHV4157
synonym: BHV-4157a
synonym: BHV4157a
synonym: FC-4157
synonym: trigriluzole
approved: f
ligand name: troriluzole
type: SyntheticOrganicLigand

compound 7 [PMID: 32302132]
canonical SMILES: OC(=O)CCCCCCCNn1nnc2c1cccc2
isomeric SMILES: OC(=O)CCCCCCCNn1nnc2c1cccc2
in ch i key: XRQULSHHDALTQA-UHFFFAOYSA-N
in ch i: InChI=1S/C14H20N4O2/c19-14(20)10-4-2-1-3-7-11-15-18-13-9-6-5-8-12(13)16-17-18/h5-6,8-9,15H,1-4,7,10-11H2,(H,19,20)
comment: This is the first reported inhibitor with selectivity for Cytochrome P450 4Z1 (CYP4Z1) <Reference id=41292/>. It provides an novel tool for further exploring the biochemical role of CYP4Z1 and its proposed association with breast cancer.
iupac name: 8-(benzotriazol-1-ylamino)octanoic acid
synonym: 8-[(1H-1,2,3-Benzotriazol-1-yl)amino]octanoic Acid
approved: f
ligand name: compound 7 [PMID: 32302132]
type: SyntheticOrganicLigand

HET0016
canonical SMILES: CCCCc1ccc(c(c1)C)N=CNO
isomeric SMILES: CCCCc1ccc(c(c1)C)N=CNO
in ch i key: LYNOGBKNFIHKLE-UHFFFAOYSA-N
in ch i: InChI=1S/C12H18N2O/c1-3-4-5-11-6-7-12(10(2)8-11)13-9-14-15/h6-9,15H,3-5H2,1-2H3,(H,13,14)
comment: HET0016 is a tool comound that is used to investigate CYP4 family enzymes. It is known to inhibit CYP4A11 <Reference id=41286/> and CYP4F <Reference id=41281/> enzymes.
iupac name: N'-(4-butyl-2-methylphenyl)-N-hydroxymethanimidamide
xref: CHEMBL267865
synonym: HET-0016
approved: f
ligand name: HET0016
type: SyntheticOrganicLigand

lazabemide
canonical SMILES: NCCNC(=O)c1ccc(cn1)Cl
isomeric SMILES: NCCNC(=O)c1ccc(cn1)Cl
in ch i key: JZXRLKWWVNUZRB-UHFFFAOYSA-N
in ch i: InChI=1S/C8H10ClN3O/c9-6-1-2-7(12-5-6)8(13)11-4-3-10/h1-2,5H,3-4,10H2,(H,11,13)
iupac name: N-(2-aminoethyl)-5-chloropyridine-2-carboxamide
xref: CHEMBL279390
approved: f
ligand name: lazabemide
type: SyntheticOrganicLigand

sesamin
in ch i key: PEYUIKBAABKQKQ-AFHBHXEDSA-N
in ch i: InChI=1S/C20H18O6/c1-3-15-17(25-9-23-15)5-11(1)19-13-7-22-20(14(13)8-21-19)12-2-4-16-18(6-12)26-10-24-16/h1-6,13-14,19-20H,7-10H2/t13-,14-,19+,20+/m0/s1
comment: Sesamin is a natural product that can be extracted from sesame seeds. It has been reported to have antihypertensive action, that is associated with inhibtion of CYP4F2-catalysed <Ligand id=4103/> (20-hydroxyeicosatetraenoic acid) production <Reference id=41284/>. 20-HETE is a vasoactive and natriuretic eicosanoid.
iupac name: 5-[(3S,3aR,6S,6aR)-3-(1,3-benzodioxol-5-yl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-6-yl]-1,3-benzodioxole
xref: CHEMBL252915
synonym: Fagarol
synonym: D-(+)-Sesamin
approved: f
ligand name: sesamin
type: NaturalProductLigand

epalrestat
canonical SMILES: C/C(=C/c1ccccc1)/C=C/1/SC(=S)N(C1=O)CC(=O)O
isomeric SMILES: C/C(=C/c1ccccc1)/C=C/1/SC(=S)N(C1=O)CC(=O)O
in ch i key: CHNUOJQWGUIOLD-NFZZJPOKSA-N
in ch i: InChI=1S/C15H13NO3S2/c1-10(7-11-5-3-2-4-6-11)8-12-14(19)16(9-13(17)18)15(20)21-12/h2-8H,9H2,1H3,(H,17,18)/b10-7+,12-8-
comment: Epalrestat (ONO-2235) is an orally active inhibitor of aldose reductase (AR). It was originally developed for potential to treat peripheral nerve (e.g. diabetic) damage <Reference id=41275/><Reference id=41274/>, but was later evaluated for anti-cancer action <Reference id=41276/><Reference id=41277/><Reference id=41278/>. Epalrestat has been shown to inhibit several isozymes of the CYP4 family in vitro , and is most potent at CYP4A11 <Reference id=41281/>.
iupac name: 2-[(5Z)-5-[(E)-2-methyl-3-phenylprop-2-enylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]acetic acid
xref: CHEMBL56337
synonym: ONO-2235
synonym: ONO2235
synonym: Kinedak®
approved: t
ligand name: epalrestat
type: SyntheticOrganicLigand

(3,5)-[19F]2-Phe-ψ-Ala
in ch i key: TWLHVEKSWVLMAU-DENHMSFDSA-N
comment: A dipeptide probe that can be radiolabelled with the [19F] isotope to study peptide transporters <Reference id=41214/>. Alternate probes were tested in this study by Arakawa et al. (2020). The L-phenylalanyl-ψ[CS-N]-L-alanine dipeptide backbone is resistant to cleavage by peptidases.
synonym: (3,5)-difluoro Phe-ψ-Ala
approved: f
ligand name: (3,5)-[19F]2-Phe-ψ-Ala
type: PeptideLigand

[18F]FEPPG
in ch i key: DXMVXTCSJSPYPD-QDHXSUQPSA-N
in ch i: InChI=1S/C14H19FN2O4/c1-17(9-13(18)19)14(20)12(16)8-10-2-4-11(5-3-10)21-7-6-15/h2-5,12H,6-9,16H2,1H3,(H,18,19)/t12-/m0/s1/i15-1
comment: A radiolabelled Gly-Sar dipeptide derivative that was designed as a potential peptide transporter PET imaging reagent <Reference id=41211/>.
iupac name: 2-[(2S)-2-amino-3-{4-[2-(18F)fluoroethoxy]phenyl}-N-methylpropanamido]acetic acid
synonym: (S)-N-(2-amino-3-(4-(2-(fluoro-18F)ethoxy)phenyl)propanoyl)-N-methylglycine
approved: f
ligand name: [18F]FEPPG
type: SyntheticOrganicLigand

DX-9065a
in ch i key: AGRCGQSFFMCBRE-ZEQRLZLVSA-N
in ch i: InChI=1S/C26H28N4O3/c1-16(27)30-11-10-23(15-30)33-22-8-6-19(7-9-22)24(26(31)32)13-17-2-3-18-4-5-20(25(28)29)14-21(18)12-17/h2-9,12,14,23-24,27H,10-11,13,15H2,1H3,(H3,28,29)(H,31,32)/t23-,24-/m0/s1
comment: DX-9065a is a synthetic, selective and direct inhibitor of coagulation factor Xa <Reference id=41193/><Reference id=41196/><Reference id=41194/><Reference id=41195/>. It inhibits thrombin generation and induces strong anticoagulant and antiplatelet actions in human blood.
iupac name: (2S)-3-(7-carbamimidoylnaphthalen-2-yl)-2-[4-[(3S)-1-ethanimidoylpyrrolidin-3-yl]oxyphenyl]propanoic acid
xref: CHEMBL19902
synonym: DX9065A
approved: f
ligand name: DX-9065a
type: SyntheticOrganicLigand

JTV-803
in ch i key: MISBTXJXWSXZBF-UHFFFAOYSA-N
in ch i: InChI=1S/C22H27N5O3/c23-21(24)27-10-5-16-1-2-19(13-17(16)14-27)30-15-22(20(28)29)6-11-26(12-7-22)18-3-8-25-9-4-18/h1-4,8-9,13H,5-7,10-12,14-15H2,(H3,23,24)(H,28,29)
comment: JTV-803 is a small molecule, selective and direct inhibitor of Factor Xa <Reference id=41199/>. It inhibits thrombus formation in in vivo models <Reference id=41197/><Reference id=41198/>. It is generally used as the mesylate salt.
iupac name: 4-[(2-carbamimidoyl-3,4-dihydro-1H-isoquinolin-7-yl)oxymethyl]-1-pyridin-4-ylpiperidine-4-carboxylic acid
xref: CHEMBL1182177
synonym: JTV803
approved: f
ligand name: JTV-803
type: SyntheticOrganicLigand

DAPT
in ch i key: DWJXYEABWRJFSP-XOBRGWDASA-N
in ch i: InChI=1S/C23H26F2N2O4/c1-14(26-19(28)12-15-10-17(24)13-18(25)11-15)21(29)27-20(16-8-6-5-7-9-16)22(30)31-23(2,3)4/h5-11,13-14,20H,12H2,1-4H3,(H,26,28)(H,27,29)/t14-,20-/m0/s1
comment: DAPT is a γ-secretase inhibitor <Reference id=41186/> that is used experimentally to inhibit NOTCH pathway signalling. Chemically it is a modified di-peptide (IUPAC Condensed name Unk-Ala-Phg-OtBu).
iupac name: tert-butyl (2S)-2-[[(2S)-2-[[2-(3,5-difluorophenyl)acetyl]amino]propanoyl]amino]-2-phenylacetate
xref: CHEMBL255682
synonym: gamma-Secretase Inhibitor IX
synonym: GSI-IX
synonym: LY-374973
approved: f
ligand name: DAPT
type: SyntheticOrganicLigand

IMR-1
canonical SMILES: CCOC(=O)COc1ccc(cc1OC)/C=C/1/SC(=S)NC1=O
isomeric SMILES: CCOC(=O)COc1ccc(cc1OC)/C=C/1/SC(=S)NC1=O
in ch i key: QHPJWPQRZMBKTG-KPKJPENVSA-N
in ch i: InChI=1S/C15H15NO5S2/c1-3-20-13(17)8-21-10-5-4-9(6-11(10)19-2)7-12-14(18)16-15(22)23-12/h4-7H,3,8H2,1-2H3,(H,16,18,22)/b12-7+
comment: IMR-1 is a small molecule inhibitor of Notch-mediated transcription <Reference id=41183/>. It binds to the intracellular domain of Notch1 and blocks recruitment of the Mastermind-like 1 protein to the Notch transcriptional activation complex on chromatin. It is an experimental tool compound.
iupac name: ethyl 2-[2-methoxy-4-[(E)-(4-oxo-2-sulfanylidene-1,3-thiazolidin-5-ylidene)methyl]phenoxy]acetate
approved: f
ligand name: IMR-1
type: SyntheticOrganicLigand

MK-0752
in ch i key: XCGJIFAKUZNNOR-UHFFFAOYSA-N
comment: MK-0752 is a γ-secretase <Reference id=41170/> and Notch pathway inhibitor that was originally intended for the treatment of Alzheimer's disease, but was later redeployed for anti-tumour potential.
iupac name: 3-[4-(4-chlorophenyl)sulfonyl-4-(2,5-difluorophenyl)cyclohexyl]propanoic acid
xref: CHEMBL4205422
synonym: MK0752
approved: f
ligand name: MK-0752
type: SyntheticOrganicLigand

crenigacestat
in ch i key: YCBAQKQAINQRFW-UGSOOPFHSA-N
in ch i: InChI=1S/C22H23F3N4O4/c1-13(27-17(31)8-9-22(23,24)25)20(32)28-18-15-6-3-2-5-14(15)16-7-4-10-26-19(16)29(11-12-30)21(18)33/h2-7,10,13,18,30H,8-9,11-12H2,1H3,(H,27,31)(H,28,32)/t13-,18-/m0/s1
comment: Crenigacestat (LY3039478) is an oral γ-secretase/NOTCH pathway inhibitor that was developed for anti-tumour potential <Reference id=41168/>. Structurally, it is a modified four amino acid peptide. It shows some selectivity for NOTCH 1 signalling <Reference id=41164/>.
iupac name: 4,4,4-trifluoro-N-[(2S)-1-[[(7S)-5-(2-hydroxyethyl)-6-oxo-7H-pyrido[2,3-d][3]benzazepin-7-yl]amino]-1-oxopropan-2-yl]butanamide
xref: CHEMBL2338397
synonym: LY3039478
synonym: LY-3039478
approved: f
ligand name: crenigacestat
type: SyntheticOrganicLigand

napabucasin
canonical SMILES: CC(=O)c1cc2c(o1)C(=O)c1c(C2=O)cccc1
isomeric SMILES: CC(=O)c1cc2c(o1)C(=O)c1c(C2=O)cccc1
in ch i key: DPHUWDIXHNQOSY-UHFFFAOYSA-N
in ch i: InChI=1S/C14H8O4/c1-7(15)11-6-10-12(16)8-4-2-3-5-9(8)13(17)14(10)18-11/h2-6H,1H3
comment: Napabucasin (BBI608) is a small molecule naphthoquinone that blocks cancer stemness properties <Reference id=41148/><Reference id=41153/>, It does this by targeting the signal transducer and activator of transcription 3 (STAT3) pathway <Reference id=36386/>. Napabucasin is orally administered, and is bioactivated by the intracellular antioxidant NAD(P)H:quinone oxidoreductase 1 (NQO1), to produce reactive oxygen species (ROS), principally NO. The high level of NO generation causes cell death, and positively correlates with the compound's anti-proliferative activity in cancer cells <Reference id=41149/>. COVID-19: Napabucasin has been proposed as a potential repurposing candidate for the treatment of COVID-19, based on a virtual screening analysis of the interaction of existing approved and experimental compounds with the SARS-CoV-2 main protease (Mpro) <Reference id=41152/>. Extensive in vitro and in vivo studies would be required to validate napabucasin's antiviral activity.
iupac name: 2-acetylbenzo[f][1]benzofuran-4,9-dione
xref: CHEMBL64130
synonym: BBI608
synonym: BBI-608
approved: f
ligand name: napabucasin
type: SyntheticOrganicLigand

MDL12330A (parent)
in ch i key: RTRIXVOSRYRSBP-VXKWHMMOSA-N
in ch i: InChI=1S/C23H36N2/c1-2-4-6-11-18-23(24-19-12-7-5-3-1)25-22-17-13-16-21(22)20-14-9-8-10-15-20/h8-10,14-15,21-22H,1-7,11-13,16-19H2,(H,24,25)/t21-,22-/m0/s1
comment: MDL12330A is a non-selective adenylyl cyclase inhibitor <Reference id=41145/>. It also modulates cyclic GMP metabolism and cyclic AMP phosphodiesterase activities <Reference id=41146/><Reference id=41147/>. It used as an experimental tool, most commonly as the hydrochloride salt.
iupac name: N-[(1S,2S)-2-phenylcyclopentyl]-1-azacyclotridecen-2-amine
xref: CHEMBL119336
synonym: MDL 12330A
synonym: MDL-12330A
synonym: RMI 12330A
synonym: RMI12330A
approved: f
ligand name: MDL12330A (parent)
type: SyntheticOrganicLigand

LY3405105
in ch i key: GRDAHPJRLCTJNA-BXKJMJEDSA-N
in ch i: InChI=1S/C26H39N7O3/c1-18(2)22-16-27-33-23(15-19(3)28-25(22)33)29-20-8-12-31(13-9-20)26(35)36-21-10-14-32(17-21)24(34)7-6-11-30(4)5/h6-7,15-16,18,20-21,29H,8-14,17H2,1-5H3/b7-6+/t21-/m0/s1
comment: LY3405105 is a clinical stage kinase inhibitor. It inhibits the activity of CDK7 and is being investigated for anti-tumour potential <Reference id=41126/>. The chemical structure is one of those claimed in Eli Lilly's patent WO2019099298A1 <Reference id=41127/>. The absolute stereochemistry of LY3405105 is unclear. Sava et al. (2020) present the structure without specified stereochemistry <Reference id=41126/>. We show the (3S) enantiomer, which is Example 1 in the patent as this was the most potent CDK7 inhibitor, and it was the example that was tested for in vitro and in vivo anti-proliferative activity..
iupac name: (3S)-1-[(2E)-4-(dimethylamino)but-2-enoyl]pyrrolidin-3-yl 4-{[5-methyl-3-(propan-2-yl)pyrazolo[1,5-a]pyrimidin-7-yl]amino}piperidine-1-carboxylate
approved: f
ligand name: LY3405105
type: SyntheticOrganicLigand

miltefosine
canonical SMILES: CCCCCCCCCCCCCCCCOP(=O)(OCC[N+](C)(C)C)[O-]
isomeric SMILES: CCCCCCCCCCCCCCCCOP(=O)(OCC[N+](C)(C)C)[O-]
in ch i key: PQLXHQMOHUQAKB-UHFFFAOYSA-N
in ch i: InChI=1S/C21H46NO4P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-20-25-27(23,24)26-21-19-22(2,3)4/h5-21H2,1-4H3
comment: Miltefosine is an antiprotozoal (anthelmintic) drug that is primarily used to treat leishmaniasis. It has additional anticancer and immunomodulatory/anti-inflammatory activities <Reference id=41306/>. The antitumour activity of miltefosine is principally mediated through the inhibition of Akt phosphorylation <Reference id=41119/>, which exerts a modulatory effect on the phosphatidylinositol 3-kinase (PI3K)-Akt/PKB cellular survival pathway.
iupac name: hexadecyl 2-(trimethylazaniumyl)ethyl phosphate
xref: CHEMBL125
synonym: Miltex®
synonym: Impavido®
synonym: D-18506
synonym: D18506
synonym: n-hexadecylphosphorylcholine
approved: t
ligand name: miltefosine
type: SyntheticOrganicLigand

berotralstat
in ch i key: UXNXMBYCBRBRFD-MUUNZHRXSA-N
in ch i: InChI=1S/C30H26F4N6O/c31-24-10-9-22(28(37-17-18-7-8-18)21-5-1-3-19(11-21)15-35)13-25(24)38-29(41)26-14-27(30(32,33)34)39-40(26)23-6-2-4-20(12-23)16-36/h1-6,9-14,18,28,37H,7-8,16-17,36H2,(H,38,41)/t28-/m1/s1
comment: Berotralstat (BCX7353) is an orally bioavailable inhibitor of plasma kallikrein, a proteinase that is encoded by the KLKB1 gene in humans <Reference id=42966/>. Plasma kallikrein cleaves Lys-Arg and Arg-Ser bonds in (human) kininogen to release bradykinin. Inhibition of this activity is exploited to reduce bradykinin levels in human disease where abnormally elevated bradykinin induces pathologic vascular permeability and swelling, as seen in patients with hereditary angioedema (HAE; caused by loss of C1 inhibitor SERPING1 expression). The 'flat' structure of berotralstat with no specified stereochemistry is claimed as compound 52h in Biocryst Pharmaceuticals' patent WO2015134998A1 <Reference id=41083/>.
iupac name: 2-[3-(aminomethyl)phenyl]-N-[5-[(R)-(3-cyanophenyl)-(cyclopropylmethylamino)methyl]-2-fluorophenyl]-5-(trifluoromethyl)pyrazole-3-carboxamide
synonym: BCX7353
synonym: BCX-7353
synonym: Orladeyo®
approved: t
ligand name: berotralstat
type: SyntheticOrganicLigand

EST64454
in ch i key: COKUNRYWXTVUAH-UHFFFAOYSA-N
in ch i: InChI=1S/C18H22F2N4O2/c1-14(25)23-8-6-22(7-9-23)10-11-26-13-15-4-5-24(21-15)16-2-3-17(19)18(20)12-16/h2-5,12H,6-11,13H2,1H3
comment: EST64454 is reported as a σ1 receptor antagonist <Reference id=41063/>. In vivo evidence suggests a role in pain management. It is one of the compounds that are claimed in patent WO2011147910A1 'Pyrazole compounds as sigma receptor inhibitors' <Reference id=41064/>.
iupac name: 1-(4-(2-((1-(3,4-difluorophenyl)-1H-pyrazol-3-yl)methoxy)ethyl)piperazin-1-yl)ethanone
synonym: compound 9k [PMID: 33237785]
synonym: EST-64454
synonym: example 39 [WO2011147910A1]
approved: f
ligand name: EST64454
type: SyntheticOrganicLigand

Ganglioside GD2
in ch i key: FFILOTSTFMXQJC-QCFYAKGBSA-N
in ch i: InChI=1S/C74H134N4O32/c1-4-6-8-10-12-14-16-18-19-21-23-25-27-29-31-33-52(89)78-43(44(84)32-30-28-26-24-22-20-17-15-13-11-9-7-5-2)40-101-69-61(95)60(94)63(50(38-81)104-69)106-70-62(96)67(64(51(39-82)105-70)107-68-55(77-42(3)83)59(93)58(92)49(37-80)103-68)110-74(72(99)100)35-46(86)54(76)66(109-74)57(91)48(88)41-102-73(71(97)98)34-45(85)53(75)65(108-73)56(90)47(87)36-79/h30,32,43-51,53-70,79-82,84-88,90-96H,4-29,31,33-41,75-76H2,1-3H3,(H,77,83)(H,78,89)(H,97,98)(H,99,100)/b32-30+/t43?,44?,45-,46-,47?,48?,49-,50-,51-,53+,54+,55-,56?,57?,58+,59-,60-,61-,62-,63-,64+,65+,66+,67-,68+,69-,70+,73-,74+/m1/s1
comment: Ganglioside GD2 is a disialoganglioside cell adhesion molecule that is expressed on tumours of neuroectodermal origin, but which has restricted presence on normal cells. It is a drug target for neuroectoderm-derived tumours and sarcomas, including neuroblastoma, retinoblastoma, melanoma and small cell lung cancer <Reference id=41056/>. Two monoclonal antibodies that target GD2 have been approved for clinical use in patients with high risk neuroblastoma: <Ligand id=7979/> (2015) and <Ligand id=11341/> (2020). Both of these mAbs stimulate antibody-dependent cell-mediated cytotoxicity (ADCC) against GD2-expressing tumour cells.
iupac name: (2R,4R,5S,6S)-2-[3-[(2S,3S,4R,6S)-6-[(2S,3R,4R,5S,6R)-5-[(2S,3R,4R,5R,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2-[(2R,3S,4R,5R,6R)-4,5-dihydroxy-2-(hydroxymethyl)-6-[(E)-3-hydroxy-2-(octadecanoylamino)octadec-4-enoxy]oxan-3-yl]oxy-3-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-3-amino-6-carboxy-4-hydroxyoxan-2-yl]-2,3-dihydroxypropoxy]-5-amino-4-hydroxy-6-(1,2,3-trihydroxypropyl)oxane-2-carboxylic acid
approved: f
ligand name: Ganglioside GD2
type: SyntheticOrganicLigand

SBP-7455
in ch i key: BQROJYIEHOOQBY-UHFFFAOYSA-N
in ch i: InChI=1S/C16H17F3N4O2/c1-24-12-6-5-10(7-13(12)25-2)22-15-20-8-11(16(17,18)19)14(23-15)21-9-3-4-9/h5-9H,3-4H2,1-2H3,(H2,20,21,22,23)
comment: SBP-7455 is a dual ULK1/2 inhibitor <Reference id=41028/>. It inhibits ULK-regulated autophagy, and synergises with the PARP inhibitor <Ligand id=7519/> to block proliferation of triple-negative breast cancer cells in vitro. UKL1 and -2 are the only serine/threonine (S/T) kinases in the core autophagy pathway, and they are considered to be relevant druggable targets based on their participation at the first committed step towards autophagy. Because tumours can become addicted to autophagy for survival, inhibition of the autophagy pathway has been examined as a novel approach to cancer therapy that might be applicable across a broad range of cancer types.
iupac name: N4-cyclopropyl-N2-(3,4-dimethoxyphenyl)-5-(trifluoromethyl)pyrimidine-2,4-diamine
synonym: SBP7455
synonym: compound 26 [PMID: 33200929]
approved: f
ligand name: SBP-7455
type: SyntheticOrganicLigand

SBI-0206965
in ch i key: NEXGBSJERNQRSV-UHFFFAOYSA-N
in ch i: InChI=1S/C21H21BrN4O5/c1-23-19(27)13-7-5-6-8-15(13)31-20-14(22)11-24-21(26-20)25-12-9-16(28-2)18(30-4)17(10-12)29-3/h5-11H,1-4H3,(H,23,27)(H,24,25,26)
comment: SBI-0206965 inhibits the autophagy regulating kinase ULK1 in biochemical and cellular assays (measuring inhibition of phosphorylation of the downstream substrates VPS34 and Beclin1), and is a tool compound for experimental applications <Reference id=41027/>. UKL1 and -2 are the only serine/threonine (S/T) kinases in the core autophagy pathway, and they are considered to be relevant druggable targets based on their participation at the first committed step towards autophagy. Because tumours can become addicted to autophagy for survival, inhibition of the autophagy pathway has been examined as a novel approach to cancer therapy that might be applicable across a broad range of cancer types.
iupac name: 2-[5-bromo-2-(3,4,5-trimethoxyanilino)pyrimidin-4-yl]oxy-N-methylbenzamide
xref: CHEMBL4128069
approved: f
ligand name: SBI-0206965
type: SyntheticOrganicLigand

BI-3802
in ch i key: GXTJETQFYHZHNB-GASCZTMLSA-N
in ch i: InChI=1S/C24H29ClN6O3/c1-14-7-15(2)12-31(11-14)24-27-10-18(25)22(29-24)28-17-5-6-19-16(8-17)9-20(23(33)30(19)4)34-13-21(32)26-3/h5-6,8-10,14-15H,7,11-13H2,1-4H3,(H,26,32)(H,27,28,29)/t14-,15+
comment: BI-3802 is a small molecule that promotes ubiquitin-mediated, proteasomal degradation of the oncogenic transcription factor BCL6 <Reference id=41021/><Reference id=41023/>. It binds to BCL6's BTB domain and initiates polymerization of BCL6 into structural foci that become targets for ubiquitination by the SIAH1 E3 ubiquitin ligase. BI-3802's mechanism of action is distinct from those of PROTACs and molecular glue type protein degraders <Reference id=41024/>. BI-3802-promoted degradation of BCL6 results in significant derepression of BCL6 target genes and anti-proliferative effects in model cancer cell lines. The chemical structure was claimed in a patent granted to Boehringer Ingelheim in 2018 <Reference id=41022/>.
iupac name: 2-[6-[[5-chloro-2-[(3S,5R)-3,5-dimethylpiperidin-1-yl]pyrimidin-4-yl]amino]-1-methyl-2-oxoquinolin-3-yl]oxy-N-methylacetamide
synonym: BI3802
approved: f
ligand name: BI-3802
type: SyntheticOrganicLigand

ONC212
in ch i key: DFULPGUTXZTYKA-UHFFFAOYSA-N
in ch i: InChI=1S/C24H23F3N4O/c25-24(26,27)19-8-6-18(7-9-19)15-31-22(32)20-16-29(14-17-4-2-1-3-5-17)12-10-21(20)30-13-11-28-23(30)31/h1-9H,10-16H2
comment: ONC212 is an imipridone-based Class A GPCR modulating compound. It is claimed to selectively target the orphan GPCR and tumour suppressor GPR132, at which it acts as an agonist and activator of Gαq signaling <Reference id=41020/><Reference id=41019/>. It does not engage dopamine D2 receptors. ONC212 exerts anti-tumour activity via oral and intraperitoneal delivery in xenograft mice.
synonym: ONC-212
synonym: example 52 [WO2017132661A2]
approved: f
ligand name: ONC212
type: SyntheticOrganicLigand

razuprotafib
in ch i key: KWJDHELCGJFUHW-SFTDATJTSA-N
in ch i: InChI=1S/C26H26N4O6S3/c1-36-26(32)29-21(15-17-6-3-2-4-7-17)24(31)27-20(22-16-38-25(28-22)23-8-5-13-37-23)14-18-9-11-19(12-10-18)30-39(33,34)35/h2-13,16,20-21,30H,14-15H2,1H3,(H,27,31)(H,29,32)(H,33,34,35)/t20-,21-/m0/s1
comment: Razuprotafib (AKB-9778) is an inhibitor of protein tyrosine phosphatase receptor type B (PTPRB). It functions to activate Tie2 and this activity blocks neovascularisation <Reference id=41015/>.
iupac name: [4-[(2S)-2-[[(2S)-2-(methoxycarbonylamino)-3-phenylpropanoyl]amino]-2-(2-thiophen-2-yl-1,3-thiazol-4-yl)ethyl]phenyl]sulfamic acid
xref: CHEMBL3931971
synonym: AKB-9778
synonym: AKB9778
synonym: Compound AA34 [US10220048]
approved: f
ligand name: razuprotafib
type: SyntheticOrganicLigand

EG00229
in ch i key: ZWWMEDURALZMEV-NSHDSACASA-N
in ch i: InChI=1S/C17H19N7O5S3/c18-17(19)20-7-2-4-11(16(26)27)21-15(25)14-10(6-8-30-14)24-32(28,29)12-5-1-3-9-13(12)23-31-22-9/h1,3,5-6,8,11,24H,2,4,7H2,(H,21,25)(H,26,27)(H4,18,19,20)/t11-/m0/s1
comment: EG00229 is a small molecule inhibitor of the binding of VEGF-A165 to its receptor neuropilin 1 (NRP1) <Reference id=41010/>. It was originally developed to block neo-vascularisation in tumours. EG00229 has subsequently been used to confirm that NRP1 is a host binding factor for both SARS-CoV and SARS-CoV-2 <Reference id=41011/>. It binds directly to the NRP1 domain that binds to the furin-cleaved S1 fragment of the viral spike protein, and by blocking this interaction EG00229 has been shown to reduce viral infection in in vitro systems.
xref: CHEMBL1078974
synonym: compound 2 [PMID: 20151671]
synonym: EG-00229
approved: f
ligand name: EG00229
type: SyntheticOrganicLigand

PF‐06928215
in ch i key: WGQGCLHXUPGUSZ-HIFRSBDPSA-N
in ch i: InChI=1S/C20H20N4O4/c25-17-10-16(12-6-2-1-3-7-12)22-18-14(11-21-24(17)18)19(26)23-15-9-5-4-8-13(15)20(27)28/h1-3,6-7,10-11,13,15,21H,4-5,8-9H2,(H,23,26)(H,27,28)/t13-,15+/m1/s1
comment: PF-06928215 is reported as a small molecule, high affinity inhibitor of cyclic GMP-AMP synthase (cGAS) <Reference id=40962/>. It was identified using a high throughput cGAS fluorescence polarisation (FP)-based assay. The action of PF-06928215 confirmed cGAS' druggability, and can be used as an experimental tool compound.
iupac name: (1R,2S)-2-[(7-oxo-5-phenyl-1H-pyrazolo[1,5-a]pyrimidine-3-carbonyl)amino]cyclohexane-1-carboxylic acid
approved: f
ligand name: PF‐06928215
type: SyntheticOrganicLigand

borrelidin
in ch i key: OJCKRNPLOZHAOU-UGKRXNSESA-N
in ch i: InChI=1S/C28H43NO6/c1-17-12-18(2)14-20(4)27(32)21(16-29)8-5-6-11-25(22-9-7-10-23(22)28(33)34)35-26(31)15-24(30)19(3)13-17/h5-6,8,17-20,22-25,27,30,32H,7,9-15H2,1-4H3,(H,33,34)/b6-5+,21-8-/t17-,18+,19-,20-,22+,23+,24-,25-,27+/m0/s1
comment: Borrelidin is a macrolide antibacterial originally isolated from Streptomyces. It is a noncompetitive inhibitor of both bacterial and eukaryotic threonyl-tRNA synthetases (also known as threonine--tRNA ligase), exhibiting antibacterial, antimalarial and antiangiogenic activities. The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY
iupac name: (1R,2R)-2-[(2S,4E,6Z,8R,9S,11R,13S,15S,16S)-7-cyano-8,16-dihydroxy-9,11,13,15-tetramethyl-18-oxo-1-oxacyclooctadeca-4,6-dien-2-yl]cyclopentane-1-carboxylic acid
xref: CHEMBL70590
synonym: (-)-borrelidin
approved: f
ligand name: borrelidin
type: NaturalProductLigand

CHMFL-PI4K-127
in ch i key: IHWSJFBJORCEAK-UHFFFAOYSA-N
comment: CHMFL-PI4K-127 is an inhibitor of P. falciparum phosphatidylinositol 4-kinase (PfP14K) with a novel bipyridine-sulfonamide chemotype. The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
iupac name: 6'-chloro-N-methyl-5'-(phenylsulfonamido)-[3,3'-bipyridine]-5-carboxamide
approved: f
ligand name: CHMFL-PI4K-127
type: SyntheticOrganicLigand

TAK-981
in ch i key: LXRZVMYMQHNYJB-UNXOBOICSA-N
comment: TAK-981 is an inhibitor of the protein post-translational modification, SUMOylation. SUMO is a small ubiquitin-like modifier that is attached to proteins by enzymes of the SUMOylation complex (sumo activating enzyme, SAE) <Reference id=40890/>, and its attachment regulates protein function. SUMOylation has emerged as an important pathway in oncogenic processes, making SAE an oncology drug target. TAK-981 inhibits SUMOylation and has been shown to induce anti-tumour immunity in preclinical models. The precise molecular target for TAK-981 has not been disclosed. The chemical structure that was submitted to the WHO for the INN subasumstat is identical to the chemical structure of TAK-981 that is held by PubChem, and is claimed in patent WO2016004136A1 by a team from Millennium Pharmaceuticals.
iupac name: [(1R,2S,4R)-4-[[5-[4-[(1R)-7-chloro-1,2,3,4-tetrahydroisoquinolin-1-yl]-5-methylthiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate
synonym: subasumstat (proposed INN)
synonym: TAK981
synonym: Example 133 [WO2016004136A1]
synonym: I-263a [WO2016004136A1]
approved: f
ligand name: TAK-981
type: SyntheticOrganicLigand

GYY4137 parent molecule
canonical SMILES: COc1ccc(cc1)P(=S)(N1CCOCC1)S
isomeric SMILES: COc1ccc(cc1)P(=S)(N1CCOCC1)S
in ch i key: QDSAKNAFJWRQIV-UHFFFAOYSA-N
in ch i: InChI=1S/C11H16NO2PS2/c1-13-10-2-4-11(5-3-10)15(16,17)12-6-8-14-9-7-12/h2-5H,6-9H2,1H3,(H,16,17)
comment: This is the parent molecule of a slow-release <Ligand id=9532/> donating molecule. It is used experimentally as the morpholine salt, morpholin-4-ium 4 methoxyphenyl(morpholino) phosphinodithioate (PubChem CID 53393943) <Reference id=15289/>, which is used as a pharmacological tool compound to study the biological functions of H2S in vitro and in vivo. H2S is a gasotransmitter that exhibits vasodilator and anti-hypertensive activity, and has anti-inflammatory effects.
iupac name: (4-methoxyphenyl)-morpholin-4-yl-sulfanyl-sulfanylidene-$l^{5}-phosphane
synonym: GYY4137
approved: f
ligand name: GYY4137 parent molecule
type: SyntheticOrganicLigand

compound 2 [PMID: 33085774]
in ch i key: KZRUOZJPVVJKAE-ZPHCEPPYSA-N
comment: Compound 2 is a representative compound from a novel class of hybrid molecules, combining structural domains from <Ligand id=6510/> and <Ligand id=5535/>. It consists of an azalide scaffold linked to a chloroquinoline aromate and demonstrates improved antimalarial efficacy over the parent compounds <Reference id=40971/>.
iupac name: (2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)-11-[(2S,3R,4S,6R)-3-[3-[(7-chloroquinolin-4-yl)amino]propoxy]-4-(dimethylamino)-6-methyloxan-2-yl]oxy-2-ethyl-3,4,10-trihydroxy-13-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-3,5,6,8,10,12,14-heptamethyl-1-oxa-6-azacyclopentadecan-15-one
xref: CHEMBL2041388
approved: f
ligand name: compound 2 [PMID: 33085774]
type: SyntheticOrganicLigand

WLL-vs
in ch i key: DKBAFRHAWTVKAD-ODGLJRBPSA-N
in ch i: InChI=1S/C31H47N5O6S/c1-21(2)16-24(10-15-43(5,40)41)33-30(38)27(17-22(3)4)35-31(39)28(34-29(37)20-36-11-13-42-14-12-36)18-23-19-32-26-9-7-6-8-25(23)26/h6-10,15,19,21-22,24,27-28,32H,11-14,16-18,20H2,1-5H3,(H,33,38)(H,34,37)(H,35,39)/b15-10+/t24-,27+,28+/m1/s1
comment: The peptide vinyl sulfone, WLL-vs, is a highly selective covalent inhibitor of the P. falciparum proteasome <Reference id=38272/>. The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
iupac name: (2S)-2-[[(2S)-3-(1H-indol-3-yl)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]-4-methyl-N-[(E,3S)-5-methyl-1-methylsulfonylhex-1-en-3-yl]pentanamide
xref: CHEMBL4456306
approved: f
ligand name: WLL-vs
type: SyntheticOrganicLigand

compound 24 [PMID: 32959656]
canonical SMILES: CN(CCNc1cc(/C=C/c2ccc(cc2)C(F)(F)F)nc2c1cc(Cl)cc2)C
isomeric SMILES: CN(CCNc1cc(/C=C/c2ccc(cc2)C(F)(F)F)nc2c1cc(Cl)cc2)C
in ch i key: AOIUKRJIEYZLAU-WEVVVXLNSA-N
in ch i: InChI=1S/C22H21ClF3N3/c1-29(2)12-11-27-21-14-18(28-20-10-8-17(23)13-19(20)21)9-5-15-3-6-16(7-4-15)22(24,25)26/h3-10,13-14H,11-12H2,1-2H3,(H,27,28)/b9-5+
comment: Compound 24 is the lead identified in a medicinal chemistry study of the 6-Chloro-2-arylvinylquinolines, a noval class of small molecules with promising antimalarial activity <Reference id=40970/>. The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
iupac name: (E)-N1-(6-Chloro-2-(4-(trifluoromethyl)styryl)quinolin-4-yl)-N2,N2-dimethylethane-1,2-diamine
approved: f
ligand name: compound 24 [PMID: 32959656]
type: SyntheticOrganicLigand

methnaridine
in ch i key: CYNAGHGKNNKEIO-UHFFFAOYSA-N
in ch i: InChI=1S/C25H28ClN5O2/c1-30(2)13-15-10-18(11-16(25(15)32)14-31(3)4)27-23-19-7-6-17(26)12-21(19)28-20-8-9-22(33-5)29-24(20)23/h6-12,32H,13-14H2,1-5H3,(H,27,28)
comment: Methnaridine is a novel benzonaphthyridine antimalarial compound, identified from a structural optimization study of <Ligand id=10086/> <Reference id=40952/>. The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
iupac name: 4-[(7-chloro-2-methoxybenzo[b][1,5]naphthyridin-10-yl)amino]-2,6-bis[(dimethylamino)methyl]phenol
approved: f
ligand name: methnaridine
type: SyntheticOrganicLigand

CpdA (parent molecule)
canonical SMILES: CNCC(c1ccc(cc1)OC(=O)C)Cl
isomeric SMILES: CNCC(c1ccc(cc1)OC(=O)C)Cl
in ch i key: VZCQEZNQVVYTJC-UHFFFAOYSA-N
in ch i: InChI=1S/C11H14ClNO2/c1-8(14)15-10-5-3-9(4-6-10)11(12)7-13-2/h3-6,11,13H,7H2,1-2H3
comment: The chloride salt of CpdA has been described as a dissociating glucocorticoid receptor (GR) ligand <Reference id=40950/><Reference id=40951/>. CpdA is a synthetic version of a plant-derived substance.
iupac name: [4-[1-chloro-2-(methylamino)ethyl]phenyl] acetate
approved: f
ligand name: CpdA (parent molecule)
type: SyntheticOrganicLigand

Radioprotectin-1
in ch i key: OVJUYQCJIFWMBI-UHFFFAOYSA-N
comment: Radioprotectin-1 is a LPA2 receptor agonist <Reference id=40932/>.
iupac name: 5-chloro-2-[4-(1,3-dioxobenzo[de]isoquinolin-2-yl)butylsulfamoyl]benzoic acid
xref: CHEMBL3322514
synonym: RP-1
approved: f
ligand name: Radioprotectin-1
type: SyntheticOrganicLigand

SAR100842
in ch i key: SOJDTNUCCXWTMG-UHFFFAOYSA-N
in ch i: InChI=1S/C27H27NO5/c1-18-6-5-7-19(14-18)12-13-33-24-15-20(10-11-23(24)32-2)25(29)28-27(26(30)31)16-21-8-3-4-9-22(21)17-27/h3-11,14-15H,12-13,16-17H2,1-2H3,(H,28,29)(H,30,31)
comment: SAR100842 is an orally active selective LPA1 receptor antagonist <Reference id=40931/>.
iupac name: 2-[[4-methoxy-3-[2-(3-methylphenyl)ethoxy]benzoyl]amino]-1,3-dihydroindene-2-carboxylic acid
xref: CHEMBL3621969
synonym: SAR-100842
synonym: Edg-2 receptor inhibitor 1
approved: f
ligand name: SAR100842
type: SyntheticOrganicLigand

CpY
canonical SMILES: CCN([C@H](c1cccc2c1oc(c2C)CC)CO)CC
isomeric SMILES: CCN([C@H](c1cccc2c1oc(c2C)CC)CO)CC
in ch i key: FXNNNICQCLNEPG-HNNXBMFYSA-N
in ch i: InChI=1S/C17H25NO2/c1-5-16-12(4)13-9-8-10-14(17(13)20-16)15(11-19)18(6-2)7-3/h8-10,15,19H,5-7,11H2,1-4H3/t15-/m0/s1
comment: CpY is a benzofuran ethanolamine derivative that behaves as a LPA1-3 receptor agonist <Reference id=40930/>.
iupac name: (2R)-2-(diethylamino)-2-(2-ethyl-3-methyl-1-benzofuran-7-yl)ethan-1-ol
approved: f
ligand name: CpY
type: SyntheticOrganicLigand

CpX
canonical SMILES: CCN([C@H](c1cccc2c1oc(c2C)C)CO)CC
isomeric SMILES: CCN([C@H](c1cccc2c1oc(c2C)C)CO)CC
in ch i key: GJLKKMYIDLNMFF-HNNXBMFYSA-N
in ch i: InChI=1S/C16H23NO2/c1-5-17(6-2)15(10-18)14-9-7-8-13-11(3)12(4)19-16(13)14/h7-9,15,18H,5-6,10H2,1-4H3/t15-/m0/s1
comment: CpX is a benzofuran ethanolamine derivative that behaves as a LPA1-3 receptor agonist <Reference id=40930/>.
iupac name: (2R)-2-(diethylamino)-2-(2,3-dimethyl-1-benzofuran-7-yl)ethan-1-ol
approved: f
ligand name: CpX
type: SyntheticOrganicLigand

CYM5520
in ch i key: FMYGNANMYYHBSU-UHFFFAOYSA-N
in ch i: InChI=1S/C21H19N3O2/c1-15-10-19(16(2)24(15)13-17-6-4-3-5-7-17)20(25)14-23-12-18(11-22)8-9-21(23)26/h3-10,12H,13-14H2,1-2H3
comment: CYM5520 is a S1P2 receptor selective allosteric agonist <Reference id=40919/>.
synonym: CYM-5520
approved: f
ligand name: CYM5520
type: SyntheticOrganicLigand

GSK2018682
in ch i key: NFIGDBFIDKDNIG-UHFFFAOYSA-N
in ch i: InChI=1S/C22H21ClN4O4/c1-13(2)30-22-17(23)11-14(12-24-22)21-25-20(26-31-21)16-5-3-6-18-15(16)8-10-27(18)9-4-7-19(28)29/h3,5-6,8,10-13H,4,7,9H2,1-2H3,(H,28,29)
comment: GSK2018682 is a S1P1/5 receptor modulator <Reference id=40916/>.
iupac name: 4-[4-[5-(5-chloro-6-propan-2-yloxypyridin-3-yl)-1,2,4-oxadiazol-3-yl]indol-1-yl]butanoic acid
xref: CHEMBL4297542
synonym: GSK-2018682
approved: f
ligand name: GSK2018682
type: SyntheticOrganicLigand

ORG 214007-0
in ch i key: BUWMTEGCNUYHSZ-JKXTWKSPSA-N
in ch i: InChI=1S/C24H23N5OS/c1-14-18-5-3-4-6-19(18)22-12-17(26-24(30)23-15(2)27-28-31-23)9-10-29(22)21-8-7-16(13-25)11-20(14)21/h3-8,11,14,17,22H,9-10,12H2,1-2H3,(H,26,30)/t14-,17-,22-/m0/s1
comment: ORG 214007-0 is a non-steroidal, selective glucocorticoid receptor (GR) modulator <Reference id=40906/>. It retains full anti-inflammatory activity compared to traditional steroidal GR modulators.
synonym: [(-)-N-(2S,10S,14bS)]-N-(8-cyano-1,2,3,4,10,14b-hexahydro-10-methyl dibenzo[c,f]pyrido[1,2-a]azepin-2-yl)-4-methyl-1,2,3-thiadiazole-5-carboxamide]]
synonym: ORG214007-0
approved: f
ligand name: ORG 214007-0
type: SyntheticOrganicLigand

4‐BCCA
canonical SMILES: CCCCC1CCC(CC1)C(=O)O
isomeric SMILES: CCCCC1CCC(CC1)C(=O)O
in ch i key: BALGERHMIXFENA-UHFFFAOYSA-N
in ch i: InChI=1S/C11H20O2/c1-2-3-4-9-5-7-10(8-6-9)11(12)13/h9-10H,2-8H2,1H3,(H,12,13)
comment: X-ray crystallography shows that 4‐BCCA inhibits AMPA receptor activity by binding (with low‐affinity) to a region in the receptor's transmembrane domain (PDB ID 6XSR) <Reference id=40896/>. The interaction was confirmed by mutagenesis of the amino acids predicted to be involved in the ligand-receptor interaction by the X-ray structure and electropysiological measurements in vitro. This discovery helps to explain the molecular mechanism underlying 4‐BCCA's anti-epileptic activity.
iupac name: 4-butylcyclohexane-1-carboxylic acid
synonym: trans‐4‐butylcyclohexane carboxylic acid
approved: f
ligand name: 4‐BCCA
type: SyntheticOrganicLigand

eclitasertib
in ch i key: XUZICJHIIJCKQQ-ZDUSSCGKSA-N
in ch i: InChI=1S/C19H18N6O3/c1-25-17-14(8-5-9-20-17)28-11-13(19(25)27)21-18(26)16-22-15(23-24-16)10-12-6-3-2-4-7-12/h2-9,13H,10-11H2,1H3,(H,21,26)(H,22,23,24)/t13-/m0/s1
comment: This chemical structure for eclitasertib (as the IUPAC name) was obtained from the special release of proposed INNs for COVID-related therapeutics that was published by the WHO in October 2020. The INN structure was identified as being identical to example 42 from Denali Therapeutics' patent WO2017136727A2. Denali claim this compound as a kinase inhibitor, the INN application refers to it as a RIP kinase inhibitor. Based on Denali's initiation of their RIPK1 inhibitor DNL758 (a.k.a. SAR443122) in clinical trial in COVID-19 patients, we speculate that example 42, DNL758/SAR443122 and eclitasertib are one and the same. We will update this record when name>structure is formally disclosed.
iupac name: 5-benzyl-N-[(3S)-5-methyl-4-oxo-2,3-dihydropyrido[3,2-b][1,4]oxazepin-3-yl]-1H-1,2,4-triazole-3-carboxamide
synonym: example 42 [WO2017136727A2]
approved: f
ligand name: eclitasertib
type: SyntheticOrganicLigand

psilocin
canonical SMILES: CN(CCc1c[nH]c2c1c(O)ccc2)C
isomeric SMILES: CN(CCc1c[nH]c2c1c(O)ccc2)C
in ch i key: SPCIYGNTAMCTRO-UHFFFAOYSA-N
in ch i: InChI=1S/C12H16N2O/c1-14(2)7-6-9-8-13-10-4-3-5-11(15)12(9)10/h3-5,8,13,15H,6-7H2,1-2H3
comment: Psilocin is the active metabolite of the naturally occurring tryptamine alkaloid psilocybine, a hallucinogenic alkaloid that can be isolated from Psilocybe mushrooms. It is an agonist of 5-HT2 receptors.
iupac name: 3-[2-(dimethylamino)ethyl]-1H-indol-4-ol
xref: CHEMBL65547
approved: f
ligand name: psilocin
type: NaturalProductLigand

nezulcitinib
in ch i key: VQIIUJSNIKEMCK-MHZLTWQESA-N
in ch i: InChI=1S/C30H37N7O2/c1-6-18-11-21(38)8-10-22(18)19-7-9-23-24(12-19)33-34-28(23)29-31-25-13-27(37(17(2)3)16-26(25)32-29)30(39)36-14-20(15-36)35(4)5/h7-12,17,20,27,38H,6,13-16H2,1-5H3,(H,31,32)(H,33,34)/t27-/m0/s1
comment: The chemical structure for this Janus kinase inhibitor was obtained from the WHO's special release of proposed INNs for COVID-related therapeutics that was published in October 2020, with the proposed INN being nezulcitinib. The structure is a match to example 1 as claimed in Theravance's 2020 patent WO2020051105A1. Analysis of Theravance's pipeline webpage and ClinicalTrials.gov suggests that this is likely to be their clinical lead TD-0903, which they identify as a lung-selective JAK inhibitor, since TD-0903 had begun evaluation in COVID-19 patients. At the point of creating this entry (Nov 2020) there had been no formal name>structure disclosure. We will update this as further details become available. In June 2021, Theravance announced that top-line results from patients with confirmed COVID-19 associated acute lung injury and impaired oxygenation, showed no statistically significant difference between nezulcitinib and placebo groups in terms of primary or secondary outcomes.
iupac name: [3-(dimethylamino)azetidin-1-yl]-[(6S)-2-[6-(2-ethyl-4-hydroxyphenyl)-1H-indazol-3-yl]-5-propan-2-yl-3,4,6,7-tetrahydroimidazo[4,5-c]pyridin-6-yl]methanone
synonym: example 1 [WO2020051105A1]
approved: f
ligand name: nezulcitinib
type: SyntheticOrganicLigand

mitoglitazone
in ch i key: IRNJSRAGRIZIHD-UHFFFAOYSA-N
in ch i: InChI=1S/C19H18N2O4S/c1-2-12-5-8-15(20-10-12)16(22)11-25-14-6-3-13(4-7-14)9-17-18(23)21-19(24)26-17/h3-8,10,17H,2,9,11H2,1H3,(H,21,23,24)
comment: Mitoglitazone is a thiazolidinedione class compound. that was developed for the treatment of non-insulin-dependent diabetes mellitus <Reference id=40860/>. It acts as an insulin sensitizer and modulates mitochondrial pyruvate transport by the mitochondrial pyruvate carrier <Reference id=40859/><Reference id=40855/>. Structurally it is an analogue of the approved antidiabetes drug <Ligand id=2694/>.
iupac name: 5-[[4-[2-(5-ethylpyridin-2-yl)-2-oxoethoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione
xref: CHEMBL146624
synonym: MSDC-0160
synonym: MSDC0160
approved: f
ligand name: mitoglitazone
type: SyntheticOrganicLigand

UK-5099
canonical SMILES: N#C/C(=C/c1cn(c2c1cccc2)c1ccccc1)/C(=O)O
isomeric SMILES: N#C/C(=C/c1cn(c2c1cccc2)c1ccccc1)/C(=O)O
in ch i key: BIZNHCWFGNKBBZ-JLHYYAGUSA-N
in ch i: InChI=1S/C18H12N2O2/c19-11-13(18(21)22)10-14-12-20(15-6-2-1-3-7-15)17-9-5-4-8-16(14)17/h1-10,12H,(H,21,22)/b13-10+
comment: UK-5099 acts as an antagonist of the mitochondrial pyruvate carrier <Reference id=40856/><Reference id=40858/><Reference id=36418/>.
iupac name: (E)-2-cyano-3-(1-phenylindol-3-yl)prop-2-enoic acid
xref: CHEMBL4303684
synonym: 2-CPIYA
synonym: UK5099
synonym: α-cyano-β-(1-phenylindol-3-yl)-acrylate
synonym: 2-Cyano-3-(1-phenylindol-3-yl)acrylate
synonym: 2-Cyano-3-(1-phenyl-1H-indol-3-yl)-acrylic acid
synonym: (E)-2-cyano-3-(1-phenyl-1H-indol-3-yl)acrylic acid
approved: f
ligand name: UK-5099
type: SyntheticOrganicLigand

α-Cyano-5-phenyl-2,4-pentadienic acid
canonical SMILES: N#C/C(=C/C=C/c1ccccc1)/C(=O)O
isomeric SMILES: N#C/C(=C/C=C/c1ccccc1)/C(=O)O
in ch i key: UBDXZYYYWGIRGN-VCABWLAWSA-N
in ch i: InChI=1S/C12H9NO2/c13-9-11(12(14)15)8-4-7-10-5-2-1-3-6-10/h1-8H,(H,14,15)/b7-4+,11-8+
comment: α-Cyano-5-phenyl-2,4-pentadienic acid acts as an antagonist of the mitochondrial pyruvate carrier <Reference id=40856/>.
iupac name: (2E,4E)-2-cyano-5-phenylpenta-2,4-dienoic acid
synonym: Alpha-Cyano-5-phenyl-2,4-pentadienic acid
synonym: ααcyano-5-phenyl-2,4-pentadienoate
approved: f
ligand name: α-Cyano-5-phenyl-2,4-pentadienic acid
type: SyntheticOrganicLigand

α-cyano-4-hydroxycinnamate
canonical SMILES: N#CC(=Cc1ccc(cc1)O)C(=O)O
isomeric SMILES: N#CC(=Cc1ccc(cc1)O)C(=O)O
in ch i key: AFVLVVWMAFSXCK-UHFFFAOYSA-N
in ch i: InChI=1S/C10H7NO3/c11-6-8(10(13)14)5-7-1-3-9(12)4-2-7/h1-5,12H,(H,13,14)
comment: α-cyano-4-hydroxycinnamate acts as an antagonist of the mitochondrial pyruvate carrier <Reference id=40856/>.
iupac name: 2-cyano-3-(4-hydroxyphenyl)prop-2-enoic acid
synonym: 2-cyano-4-hydroxycinnamate
synonym: alpha-cyano-4-hydroxycinnamate
synonym: alpha-cyano-4-hydroxycinnamic acid
approved: f
ligand name: α-cyano-4-hydroxycinnamate
type: SyntheticOrganicLigand

α-cyanocinnamate
canonical SMILES: N#C/C(=C/c1ccccc1)/C(=O)O
isomeric SMILES: N#C/C(=C/c1ccccc1)/C(=O)O
in ch i key: CDUQMGQIHYISOP-RMKNXTFCSA-N
in ch i: InChI=1S/C10H7NO2/c11-7-9(10(12)13)6-8-4-2-1-3-5-8/h1-6H,(H,12,13)/b9-6+
comment: α-cyanocinnamate acts as an antagonist of the mitochondrial pyruvate carrier <Reference id=40856/>.
iupac name: (E)-2-cyano-3-phenylprop-2-enoic acid
xref: CHEMBL77595
synonym: alpha-Cyanocinnamic acid
synonym: (2E)-2-cyano-3-phenylacrylic acid
synonym: alpha-cyanocinnamate
approved: f
ligand name: α-cyanocinnamate
type: SyntheticOrganicLigand

opiranserin
in ch i key: JQUVQWMHZSYCRQ-UHFFFAOYSA-N
in ch i: InChI=1S/C21H34N2O5/c1-6-7-10-28-19-17(25-4)13-16(14-18(19)26-5)20(24)22-15-21(23(2)3)8-11-27-12-9-21/h13-14H,6-12,15H2,1-5H3,(H,22,24)
comment: Opiranserin (VVZ-149) is a dual glycine transporter 2 (GlyT2) inhibitor and serotonin 5-HT2A receptor antagonist <Reference id=40849/>. It was developed as a novel non-opioid analgesic.
xref: CHEMBL4228903
synonym: VVZ-149
synonym: VVZ149
approved: f
ligand name: opiranserin
type: SyntheticOrganicLigand

GT-0198
in ch i key: IVOIYPHGIHJNMU-UHFFFAOYSA-N
in ch i: InChI=1S/C21H23F3N2O2/c1-26-12-10-18(11-13-26)25-20(27)16-4-2-15(3-5-16)14-28-19-8-6-17(7-9-19)21(22,23)24/h2-9,18H,10-14H2,1H3,(H,25,27)
comment: GT-0198 is a glycine transporter 2 (GlyT2) inhibitor <Reference id=40848/>. It is active in vivo, producing an analgesic effect in a mouse model of neuropathic pain.
xref: CHEMBL3325507
synonym: GT0198
approved: f
ligand name: GT-0198
type: SyntheticOrganicLigand

ASP2535
in ch i key: FQGLDGKVKDPVLO-UHFFFAOYSA-N
in ch i: InChI=1S/C22H18N6O/c1-14(2)21-24-25-22(28(21)19-10-6-9-18-20(19)27-29-26-18)16-11-12-17(23-13-16)15-7-4-3-5-8-15/h3-14H,1-2H3
comment: ASP2535 is a glycine transporter-1 (GlyT1) inhibitor <Reference id=40847/>. It exhibits 50-fold selectivity for rat GlyT1 over rat GlyT2, and is orally bioavailable.
iupac name: 4-[3-(6-phenylpyridin-3-yl)-5-propan-2-yl-1,2,4-triazol-4-yl]-2,1,3-benzoxadiazole
xref: CHEMBL4303475
synonym: ASP 2535
synonym: ASP-2535
approved: f
ligand name: ASP2535
type: SyntheticOrganicLigand

bemnifosbuvir
in ch i key: OISLSHLAXHALQZ-LZEIJKKFSA-N
in ch i: InChI=1S/C24H33FN7O7P/c1-13(2)37-21(34)14(3)31-40(35,39-15-9-7-6-8-10-15)36-11-16-18(33)24(4,25)22(38-16)32-12-28-17-19(27-5)29-23(26)30-20(17)32/h6-10,12-14,16,18,22,33H,11H2,1-5H3,(H,31,35)(H3,26,27,29,30)/t14-,16+,18+,22+,24+,40-/m0/s1
comment: AT-527 is the orally bioavailable hemi-sulfate salt of AT-511, which is a direct-acting antiviral compound that disrupts activity of the viral RNA polymerase <Reference id=40800/>. It was originally developed to combat hepatitis C (HCV) infection, but has been redeployed for SARS-CoV-2. Chemically AT-527 is a phosphoramidate purine nucleotide and it is metabolised to a biologically active guanosine triphosphate analogue in vivo. Preclinical results showing pan-genotype activity against HCV were published in early 2020 <Reference id=40801/>. In October 2020 anti-SARS-CoV-2 activity was reported in preprint format <Reference id=40802/>, which converted to full peer reviewed publication in March 2021 <Reference id=42426/>. AT-527 was developed by Atea Pharmaceuticals <Reference id=42664/>. In October 2020 it was announced that Roche were purchasing the rights to AT-527 (and gave it the research code RO7496998) outside of the US. In the same press release, it was revealed that AT-527 would be evaluated in Phase 3 trial in early 2021 to determine its efficacy as an early treatment for COVID-19 in non-hospitalised patients. This is a complex molecule with 5 stereo-centres, so there are several CIDs with the same connectivity in PubChem. We chose to represent the molecule from CID 122527275 as it is linked to a FDA UNique Ingredient Identifier (UNII) code. This CID represents the parent molecule. For the hemi-sulfate salt structure see PubChem CID 155926085.
synonym: AT527
synonym: RO7496998
synonym: RO-7496998
synonym: AT-527
approved: f
ligand name: bemnifosbuvir
type: SyntheticOrganicLigand

compound 27 [PMID: 32945666]
in ch i key: LIARSLHDKGMNOW-UHFFFAOYSA-N
in ch i: InChI=1S/C30H26N4O/c1-19-26-27(23-12-8-9-13-25(23)35)24(18-31)28(20-14-16-21(17-15-20)30(2,3)4)32-29(26)34(33-19)22-10-6-5-7-11-22/h5-17,35H,1-4H3
comment: Compound 27 is the most potent hit from a series of pyrazolo[3,4-b]pyridines compounds with dual-stage antimalarial activity <Reference id=40972/>. The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
iupac name: 6-(4-tert-Butylphenyl)-4-(2-hydroxyphenyl)-3-methyl-1-phenyl-1H-pyrazolo[3,4-b]pyridine-5-carbonitrile
approved: f
ligand name: compound 27 [PMID: 32945666]
type: SyntheticOrganicLigand

enerisant
in ch i key: IABXVJILZYNSTM-GOSISDBHSA-N
in ch i: InChI=1S/C22H30N4O3/c1-18-4-2-9-24(18)10-3-13-29-21-7-5-20(6-8-21)26-17-19(16-23-26)22(27)25-11-14-28-15-12-25/h5-8,16-18H,2-4,9-15H2,1H3/t18-/m1/s1
comment: Enerisant is a selective histamine H3 receptor antagonist/inverse agonist that was designed by Taisho Pharmaceutical Co. <Reference id=40799/>. It exerts wake-promoting and procognitive effects in rodents.
iupac name: [1-[4-[3-[(2R)-2-methylpyrrolidin-1-yl]propoxy]phenyl]pyrazol-4-yl]-morpholin-4-ylmethanone
approved: f
ligand name: enerisant
type: SyntheticOrganicLigand

AP1189
in ch i key: ZSDGHWLLLGYAJV-LDRJOUGUSA-N
in ch i: InChI=1S/C14H14N6O2/c15-14(16)18-17-9-3-5-11-6-4-10-19(11)12-7-1-2-8-13(12)20(21)22/h1-10H,(H4,15,16,18)/b5-3+,17-9-
comment: AP1189 is a biased agonist of melanocortin (MC) receptors. It was designed to elicit the proresolving properties of the MC1 and MC3 receptors in inflammation, whilst sparing their melanogenic effects <Reference id=40797/>. This is achieved by bias towards ERK1/2 phosphorylation and and Ca2+ mobilisation rather than inducing canonical cAMP production. The chemical structure is claimed in Action Pharma's patent WO2007141343A1 (compound 2/example 19) <Reference id=40798/>. SARS-CoV-2 and COVID-19: The proresolving activity of AP1189 is being investigated as a mechanism to combat the dysfunctional immune response in COVID-19 patients.
iupac name: 2-[(Z)-[(E)-3-[1-(2-nitrophenyl)pyrrol-2-yl]prop-2-enylidene]amino]guanidine
synonym: example 19 [WO2007141343A1]
synonym: AP-1189
approved: f
ligand name: AP1189
type: SyntheticOrganicLigand

NYX-2925
in ch i key: NFXPEHLDVKVVKA-ISTVAULSSA-N
in ch i: InChI=1S/C14H23N3O4/c1-8(2)12(20)17-6-4-5-14(17)7-16(13(14)21)10(9(3)18)11(15)19/h8-10,18H,4-7H2,1-3H3,(H2,15,19)/t9-,10+,14-/m1/s1
comment: NYX-2925 is a oral, brain-penetrating, NMDA receptor modulator that was developed by Aptinyx <Reference id=40776/>. It acts as a co-agonist to glutamate and partially activates NMDARs. NYX-2925 is being investigated for potential to modulate neural pathways relevant for chronic pain.
iupac name: (2S,3R)-3-hydroxy-2-[(4R)-5-(2-methylpropanoyl)-3-oxo-2,5-diazaspiro[3.4]octan-2-yl]butanamide
synonym: NYX2925
approved: f
ligand name: NYX-2925
type: SyntheticOrganicLigand

R-VK4-40
in ch i key: OIRZLTZLOKARTG-HXUWFJFHSA-N
in ch i: InChI=1S/C25H31ClN4O2/c1-2-18-7-5-9-23(24(18)26)30-14-12-29(13-15-30)17-20(31)10-11-27-25(32)22-16-19-6-3-4-8-21(19)28-22/h3-9,16,20,28,31H,2,10-15,17H2,1H3,(H,27,32)/t20-/m1/s1
comment: R-VK4-40 is a selective dopamine D3 receptor antagonist <Reference id=40772/><Reference id=40773/>. It has been examined in animal models for potential to combat opioid abuse and addiction.
iupac name: N-[(3R)-4-[4-(2-chloro-3-ethylphenyl)piperazin-1-yl]-3-hydroxybutyl]-1H-indole-2-carboxamide
approved: f
ligand name: R-VK4-40
type: SyntheticOrganicLigand

CC-90011
in ch i key: NBAIXBAUHIQQGF-UHFFFAOYSA-N
in ch i: InChI=1S/C24H23F2N5O2/c1-30-23(32)21(14-5-6-20(33-2)19(26)11-14)22(15-3-4-16(13-27)18(25)12-15)29-24(30)31-9-7-17(28)8-10-31/h3-6,11-12,17H,7-10,28H2,1-2H3
comment: CC-90011 is a clinical stage, selective lysine specific demethylase 1 (LSD1) inhibitor <Reference id=40730/>. It is a reversible inhibitor. LSD1 inhibitors have potential to treat certain cancers <Reference id=40733/><Reference id=40734/>.
synonym: CC90011
synonym: compound 11 [PMID: 33034194]
approved: f
ligand name: CC-90011
type: SyntheticOrganicLigand

belzutifan
in ch i key: LOMMPXLFBTZENJ-ZACQAIPSSA-N
in ch i: InChI=1S/C17H12F3NO4S/c1-26(23,24)12-3-2-11(13-14(12)17(22)16(20)15(13)19)25-10-5-8(7-21)4-9(18)6-10/h2-6,15-17,22H,1H3/t15-,16-,17+/m1/s1
comment: Belzutifan (previously PT2977 and MK-6482) binds to and inhibits HIF-2α function, and has been developed as a novel cancer therapeutic <Reference id=40435/>. HIF-2α is a transcription factor component that is established as an oncogneic driver of ccRCC, via loss of its interaction with the tumour suppressor von Hippel-Lindau (VHL), which results in disrupted proteasomal degradation and thereby accumulation of HIF-2α. Elevated HIF-2α promotes increased expression of hypoxia-responsive genes which regulate processes including angiogenesis, proliferation, migration, and immune evasion.
synonym: MK6482
synonym: PT2977
synonym: compound 2 [PMID: 31282155]
synonym: MK-6482
synonym: Welireg®
approved: t
ligand name: belzutifan
type: SyntheticOrganicLigand

BAY-6672
in ch i key: YQOLEILXOBUDMU-KRWDZBQOSA-N
comment: BAY-6672 is a potent, selective and orally bioavailable prostanoid FP receptor antagonist <Reference id=40729/>. It was developed to examine the potential of FP antagonism as an antifibrotic modality, particularly for the treatment of idiopathic pulmonary fibrosis (IPF). BAY-6672 has demonstrated efficacy in a preclinical animal model of lung fibrosis.
iupac name: (4R)-5-[(6-bromo-3-methyl-2-pyrrolidin-1-ylquinoline-4-carbonyl)amino]-4-(2-chlorophenyl)pentanoic acid
synonym: BAY6672
synonym: compound 46 [PMID: 32969660]
approved: f
ligand name: BAY-6672
type: SyntheticOrganicLigand

compound 2 [PMID: 28621538]
in ch i key: CWZUTHDJLNZLCM-DFBGVHRSSA-N
in ch i: InChI=1S/C21H19BrN6O3/c22-16-6-3-7-17(24-16)25-21(31)15-9-11-8-14(11)28(15)18(29)10-27-13-5-2-1-4-12(13)19(26-27)20(23)30/h1-7,11,14-15H,8-10H2,(H2,23,30)(H,24,25,31)/t11-,14-,15+/m1/s1
comment: Compound 2 is a small molecule complement factor D inhibitor that has been developed by Novartis <Reference id=40727/>. The compound is orally bioavailable, and blocks activation of the complement alternative pathway in vitro and in vivo. Factor D inhibitors act upstream of the factor C5-targeting drugs such as <Ligand id=6884/> and <Ligand id=10168/>, and small molecules are intended to offer more flexible therapeutic options than the existing monoclonal antibodies.
iupac name: 1-[2-[(1R,3S,5R)-3-[(6-bromopyridin-2-yl)carbamoyl]-2-azabicyclo[3.1.0]hexan-2-yl]-2-oxoethyl]indazole-3-carboxamide
xref: CHEMBL3683753
synonym: example 727 [WO2012093101A1]
approved: f
ligand name: compound 2 [PMID: 28621538]
type: SyntheticOrganicLigand

AZD9977
in ch i key: MBKYLPOPYYLTNW-ZDUSSCGKSA-N
in ch i: InChI=1S/C20H18FN3O5/c1-22-18(25)8-13-9-28-17-7-12(21)3-4-15(17)24(13)20(27)11-2-5-16-14(6-11)23-19(26)10-29-16/h2-7,13H,8-10H2,1H3,(H,22,25)(H,23,26)/t13-/m0/s1
comment: AZD9977 is a selective, nonsteroidal, mineralocorticoid receptor modulator <Reference id=40659/><Reference id=40661/><Reference id=40662/>. It acts as a partial antagonist, but is equally as efficacious as <Ligand id=2876/> in organ protection in a rat model of cardio-renal disease.
iupac name: 2-[(3S)-7-fluoro-4-(3-oxo-4H-1,4-benzoxazine-6-carbonyl)-2,3-dihydro-1,4-benzoxazin-3-yl]-N-methylacetamide
xref: CHEMBL3916929
synonym: AZD-9977
synonym: (S)-1 [PMID: 30596500]
approved: f
ligand name: AZD9977
type: SyntheticOrganicLigand

AR291903
in ch i key: PKSMEKUMTYWBCL-UHFFFAOYSA-N
in ch i: InChI=1S/C26H29F5N2O/c1-24(2,3)17-7-8-21-18(15-17)25(9-12-32(13-10-25)14-11-26(29,30)31)16-33(21)23(34)22-19(27)5-4-6-20(22)28/h4-8,15H,9-14,16H2,1-3H3
comment: AR291903 is an inverse agonist of the MAS1 receptor <Reference id=40656/>. Two additional inverse agonists are described in this report: AR244555 (EC50 201 nM) and AR305352 (EC50 135 nM).
iupac name: 5-tert-butyl-1-(2,6-difluorobenzoyl)-1'-(3,3,3-trifluoropropyl)-1,2-dihydrospiro[indole-3,4'-piperidine]
approved: f
ligand name: AR291903
type: SyntheticOrganicLigand

AR234958
in ch i key: YSSZKXGYBVLEJP-UHFFFAOYSA-N
comment: AR234958 is a small molecule AT2R agonist <Reference id=40656/>. AR234960 (EC50 239 nM) is another selective agonist from this report.
iupac name: 1-(4-fluorophenyl)-4-{[4-(3-fluorophenyl)-1-(2-methoxy-4-nitrobenzenesulfonyl)pyrrolidin-3-yl]methyl}piperazine
approved: f
ligand name: AR234958
type: SyntheticOrganicLigand

AZD1390
in ch i key: VQSZIPCGAGVRRP-UHFFFAOYSA-N
in ch i: InChI=1S/C27H32FN5O2/c1-18(2)33-26-21-14-20(22(28)15-23(21)29-17-24(26)31(3)27(33)34)19-8-9-25(30-16-19)35-13-7-12-32-10-5-4-6-11-32/h8-9,14-18H,4-7,10-13H2,1-3H3
comment: AZD1390 is an oral, brain-penetrant ATM kinase inhibitor <Reference id=40640/>. Structurally, AZD1390 is from the same chemical series as <Ligand id=9942/>, but is optimised to cross the blood-brain barrier <Reference id=44187/><Reference id=44186/>. Mechanistically, blocking ATM disrupts DNA damage repair and sensitises cancer cells to radiotherapy. This induces G2 cell cycle arrest and the development of micronuclei, and ultimately leads to apoptosis. Experimental evidence suggests that AZD1390 is able to promote neurite outgrowth in vitro, and axon regeneration and functional recovery in in vivo models of spinal cord injury <Reference id=44188/>.
iupac name: 7-fluoro-3-methyl-8-[6-(3-piperidin-1-ylpropoxy)pyridin-3-yl]-1-propan-2-ylimidazo[4,5-c]quinolin-2-one
approved: f
ligand name: AZD1390
type: SyntheticOrganicLigand

Ani9
canonical SMILES: COc1ccccc1C=NNC(=O)COc1ccc(cc1C)Cl
isomeric SMILES: COc1ccccc1C=NNC(=O)COc1ccc(cc1C)Cl
in ch i key: KDALDZRKOBJXIE-UHFFFAOYSA-N
in ch i: InChI=1S/C17H17ClN2O3/c1-12-9-14(18)7-8-15(12)23-11-17(21)20-19-10-13-5-3-4-6-16(13)22-2/h3-10H,11H2,1-2H3,(H,20,21)
comment: Ani9 acts as an inhibitor of the calcium activated chloride channel CaCC (TMEM16A, ANO1) <Reference id=40639/>.
approved: f
ligand name: Ani9
type: SyntheticOrganicLigand

lonodelestat
in ch i key: JMWYNUHGKFJVIB-QGFXQWJDSA-N
comment: Lonodelestat is a modified cyclic peptide (macrolide) that acts as a selective inhibitor of human neutrophil elastase (hNE). It is being developed by Santhera Pharmaceuticals, under license from its originator Polyphor. In April 2020 Santhera announced a COVID-19 collaboration, in which non-clinical research will be conducted by Cold Spring Harbor Laboratory (CSHL) to further validate hNE as a target and assess lonodelestat as a potential agent for treating COVID-19-related acute respiratory distress syndrome (ARDS).
synonym: cyclo[Ala-Ser-Ile-Pro-Pro-Gln-Lys-Tyr-D-Pro-Pro-Nle(Bu)-Glu-Thr]
synonym: POL6014
synonym: POL-6014
approved: f
ligand name: lonodelestat
type: SyntheticOrganicLigand

GSK'547
in ch i key: SJVGFKBLUYAEOK-SFHVURJKSA-N
in ch i: InChI=1S/C20H18F2N6O/c21-15-7-14(8-16(22)9-15)18-1-4-26-28(18)20(29)13-2-5-27(6-3-13)19-10-17(11-23)24-12-25-19/h4,7-10,12-13,18H,1-3,5-6H2/t18-/m0/s1
comment: GSK'547 is a RIP kinase 1 (RIPK1) inhibitor <Reference id=40632/><Reference id=40633/>. It was investigated for anti-cancer potential, but the development program was terminated.
iupac name: 6-[4-[(3S)-3-(3,5-difluorophenyl)-3,4-dihydropyrazole-2-carbonyl]piperidin-1-yl]pyrimidine-4-carbonitrile
synonym: GSK-547
synonym: GSK547
synonym: example 6 [WO2020044206A1]
approved: f
ligand name: GSK'547
type: SyntheticOrganicLigand

paritaprevir
in ch i key: UAUIUKWPKRJZJV-QPLHLKROSA-N
in ch i: InChI=1S/C40H43N7O7S/c1-24-21-42-33(22-41-24)35(48)43-32-16-6-4-2-3-5-11-25-20-40(25,39(51)46-55(52,53)27-17-18-27)45-36(49)34-19-26(23-47(34)38(32)50)54-37-30-14-8-7-12-28(30)29-13-9-10-15-31(29)44-37/h5,7-15,21-22,25-27,32,34H,2-4,6,16-20,23H2,1H3,(H,43,48)(H,45,49)(H,46,51)/b11-5-/t25-,26-,32+,34+,40-/m1/s1
comment: Paritaprevir is an orally bioavailable, direct-acting inhibitor of the hepatitis C virus (HCV) non-structural protein 3 and 4A (NS3/NS4A) protease complex <Reference id=40631/>. It blocks NS3/NS4A protease-mediated polyprotein maturation, thus disrupting viral replication.
xref: CHEMBL3391662
synonym: ABT-450
synonym: ABT450
synonym: veruprevir (deprecated INN)
synonym: Viekirax® (ombitasvir + paritaprevir + ritonavir; EU)
approved: t
ligand name: paritaprevir
type: SyntheticOrganicLigand

DL-175
canonical SMILES: [O-][n+]1cccc(c1)CCOc1ccc(c2c1cccc2)Cl
isomeric SMILES: [O-][n+]1cccc(c1)CCOc1ccc(c2c1cccc2)Cl
in ch i key: FXOVKEUUTXBOJZ-UHFFFAOYSA-N
in ch i: InChI=1S/C17H14ClNO2/c18-16-7-8-17(15-6-2-1-5-14(15)16)21-11-9-13-4-3-10-19(20)12-13/h1-8,10,12H,9,11H2
comment: Orthosteric agonist of GPR84.
iupac name: 3-(2-((4-chloronaphthalen-1-yl)oxy)ethyl)pyridine 1-oxide
approved: f
ligand name: DL-175
type: SyntheticOrganicLigand

ZQ-16
canonical SMILES: CCCCCCSc1nc(O)cc(=O)[nH]1
isomeric SMILES: CCCCCCSc1nc(O)cc(=O)[nH]1
in ch i key: UYXOAKRMLQKLQX-UHFFFAOYSA-N
in ch i: InChI=1S/C10H16N2O2S/c1-2-3-4-5-6-15-10-11-8(13)7-9(14)12-10/h7H,2-6H2,1H3,(H2,11,12,13,14)
comment: Orthosteric agonist of GPR84.
iupac name: 2-hexylsulfanyl-6-hydroxy-3H-pyrimidin-4-one
approved: f
ligand name: ZQ-16
type: SyntheticOrganicLigand

N-acetyl-4-benzoquinoneimine
canonical SMILES: O=C1C=CC(=NC(=O)C)C=C1
isomeric SMILES: O=C1C=CC(=NC(=O)C)C=C1
in ch i key: URNSECGXFRDEDC-UHFFFAOYSA-N
in ch i: InChI=1S/C8H7NO2/c1-6(10)9-7-2-4-8(11)5-3-7/h2-5H,1H3
iupac name: N-(4-oxo-1-cyclohexa-2,5-dienylidene)acetamide
xref: CHEMBL33232
synonym: N-acetyl-p-benzo-quinoneimine
synonym: napqi
approved: f
ligand name: N-acetyl-4-benzoquinoneimine
type: SyntheticOrganicLigand

ombitasvir
in ch i key: PIDFDZJZLOTZTM-KHVQSSSXSA-N
in ch i: InChI=1S/C50H67N7O8/c1-30(2)42(53-48(62)64-8)46(60)55-28-10-12-40(55)44(58)51-35-20-14-32(15-21-35)38-26-27-39(57(38)37-24-18-34(19-25-37)50(5,6)7)33-16-22-36(23-17-33)52-45(59)41-13-11-29-56(41)47(61)43(31(3)4)54-49(63)65-9/h14-25,30-31,38-43H,10-13,26-29H2,1-9H3,(H,51,58)(H,52,59)(H,53,62)(H,54,63)/t38-,39-,40-,41-,42-,43-/m0/s1
comment: Ombitasvir is an orally available, direct-acting inhibitor of the hepatitis C virus (HCV) non-structural protein 5A (NS5A) replication complex <Reference id=40629/>. In common with many other NS5A inhibitors it is a dinucleotide derivative.
iupac name: methyl N-[(2S)-1-[(2S)-2-[[4-[(2S,5S)-1-(4-tert-butylphenyl)-5-[4-[[(2S)-1-[(2S)-2-(methoxycarbonylamino)-3-methylbutanoyl]pyrrolidine-2-carbonyl]amino]phenyl]pyrrolidin-2-yl]phenyl]carbamoyl]pyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl]carbamate
xref: CHEMBL3127326
synonym: ABT-267
synonym: ABT267
synonym: Technivie® (ombitasvir + paritaprevir + ritonavir)
synonym: compound 38 [PMID: 24400777]
synonym: Viekirax® (ombitasvir + paritaprevir + ritonavir; EU)
approved: t
ligand name: ombitasvir
type: SyntheticOrganicLigand

ledipasvir
in ch i key: VRTWBAAJJOHBQU-KMWAZVGDSA-N
in ch i: InChI=1S/C49H54F2N8O6/c1-24(2)39(56-46(62)64-5)44(60)58-23-48(15-16-48)21-38(58)42-52-22-37(55-42)28-9-13-32-31-12-8-26(18-33(31)49(50,51)34(32)19-28)27-10-14-35-36(20-27)54-43(53-35)41-29-7-11-30(17-29)59(41)45(61)40(25(3)4)57-47(63)65-6/h8-10,12-14,18-20,22,24-25,29-30,38-41H,7,11,15-17,21,23H2,1-6H3,(H,52,55)(H,53,54)(H,56,62)(H,57,63)/t29-,30+,38-,39-,40-,41-/m0/s1
comment: Ledipasvir is an orally available, direct-acting inhibitor of the hepatitis C virus (HCV) non-structural protein 5A (NS5A) replication complex <Reference id=40630/>.
iupac name: methyl N-[(2S)-1-[(6S)-6-[5-[9,9-difluoro-7-[2-[(1R,3S,4S)-2-[(2S)-2-(methoxycarbonylamino)-3-methylbutanoyl]-2-azabicyclo[2.2.1]heptan-3-yl]-3H-benzimidazol-5-yl]fluoren-2-yl]-1H-imidazol-2-yl]-5-azaspiro[2.4]heptan-5-yl]-3-methyl-1-oxobutan-2-yl]carbamate
xref: CHEMBL2374220
synonym: GS-5885
synonym: GS5885
synonym: Harvoni® (ledipasvir + sofosbuvir)
approved: t
ligand name: ledipasvir
type: SyntheticOrganicLigand

dasabuvir
in ch i key: NBRBXGKOEOGLOI-UHFFFAOYSA-N
in ch i: InChI=1S/C26H27N3O5S/c1-26(2,3)22-15-20(29-11-10-23(30)27-25(29)31)14-21(24(22)34-4)18-7-6-17-13-19(28-35(5,32)33)9-8-16(17)12-18/h6-15,28H,1-5H3,(H,27,30,31)
comment: Dasabuvir is a non-nucleoside inhibitor of the hepatitis C virus (HCV) RNA-dependent RNA polymerase NS5B <Reference id=40628/>. It blocks viral RNA replication.
iupac name: N-[6-[3-tert-butyl-5-(2,4-dioxopyrimidin-1-yl)-2-methoxyphenyl]naphthalen-2-yl]methanesulfonamide
xref: CHEMBL3137312
synonym: ABT-333
synonym: ABT333
synonym: Exviera®
approved: t
ligand name: dasabuvir
type: SyntheticOrganicLigand

velpatasvir
in ch i key: FHCUMDQMBHQXKK-CDIODLITSA-N
in ch i: InChI=1S/C49H54N8O8/c1-26(2)41(54-48(60)63-5)47(59)57-27(3)12-17-38(57)45-51-36-16-14-30-20-35-33-15-13-31(19-32(33)25-65-40(35)21-34(30)43(36)53-45)37-22-50-44(52-37)39-18-28(24-62-4)23-56(39)46(58)42(55-49(61)64-6)29-10-8-7-9-11-29/h7-11,13-16,19-22,26-28,38-39,41-42H,12,17-18,23-25H2,1-6H3,(H,50,52)(H,51,53)(H,54,60)(H,55,61)/t27-,28-,38-,39-,41-,42+/m0/s1
comment: Velpatasvir is a direct-acting inhibitor of hepatitis C virus (HCV) non-structural protein 5A (NS5A) replication complex <Reference id=40626/>. It targets viral RNA replication and viron assembly.
xref: CHEMBL3545062
synonym: GS-5816
synonym: GS5816
synonym: Epclusa® (sofosbuvir + velpatasvir)
synonym: Vosevi® (sofosbuvir + velpatasvir + voxilaprevi)
approved: t
ligand name: velpatasvir
type: SyntheticOrganicLigand

pibrentasvir
in ch i key: VJYSBPDEJWLKKJ-NLIMODCCSA-N
comment: Pibrentasvir is an oral, direct-acting inhibitor of hepatitis C virus (HCV) non-structural protein 5A (NS5A) replication complex. It targets viral RNA replication and viron assembly.
xref: CHEMBL3545123
synonym: Mavyret® (glecaprevir + pibrentasvir)
synonym: ABT-530
synonym: ABT530
approved: t
ligand name: pibrentasvir
type: SyntheticOrganicLigand

glecaprevir
in ch i key: MLSQGNCUYAMAHD-ITNVBOSISA-N
comment: Glecaprevir is an orally available anti-hepatitis C virus (HCV) drug. It is a direct-acting inhibitor of the HCV NS3/4A protease, and thereby targets viral RNA replication.
xref: CHEMBL3545363
synonym: ABT-493
synonym: ABT493
synonym: Mavyret® (glecaprevir + pibrentasvir)
synonym: Maviret®
approved: t
ligand name: glecaprevir
type: SyntheticOrganicLigand

daclatasvir
in ch i key: FKRSSPOQAMALKA-CUPIEXAXSA-N
in ch i: InChI=1S/C40H50N8O6/c1-23(2)33(45-39(51)53-5)37(49)47-19-7-9-31(47)35-41-21-29(43-35)27-15-11-25(12-16-27)26-13-17-28(18-14-26)30-22-42-36(44-30)32-10-8-20-48(32)38(50)34(24(3)4)46-40(52)54-6/h11-18,21-24,31-34H,7-10,19-20H2,1-6H3,(H,41,43)(H,42,44)(H,45,51)(H,46,52)/t31-,32-,33-,34-/m0/s1
comment: Daclatasvir is an orally available anti-hepatitis C virus (HCV) drug, It is a direct-acting inhibitor of the non-structural protein 5A (NS5A) replication complex of HCV <Reference id=40624/>. Blocking NS5A function inhibits viral RNA replication and virion assembly.
iupac name: methyl N-[(2S)-1-[(2S)-2-[5-[4-[4-[2-[(2S)-1-[(2S)-2-(methoxycarbonylamino)-3-methylbutanoyl]pyrrolidin-2-yl]-1H-imidazol-5-yl]phenyl]phenyl]-1H-imidazol-2-yl]pyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl]carbamate
xref: CHEMBL2023898
synonym: BMS-790052
synonym: BMS790052
synonym: Daklinza®
approved: t
ligand name: daclatasvir
type: SyntheticOrganicLigand

mavacamten
in ch i key: RLCLASQCAPXVLM-NSHDSACASA-N
in ch i: InChI=1S/C15H19N3O2/c1-10(2)18-14(19)9-13(17-15(18)20)16-11(3)12-7-5-4-6-8-12/h4-11,16H,1-3H3,(H,17,20)/t11-/m0/s1
comment: Mavacamten (MYK-461) is an orally active myosin allosteric modulator <Reference id=40621/> that was developed by MyoKardia as a novel treatment for obstructive hypertrophic cardiomyopathy (HCM). In 2020 MyoKardia was bought by Bristol Myers Squibb. The compound interacts with both α and β cardiac myosins in vitro. Preclinical pharmacokinetics are reported in <Reference id=40620/>. Mavacamten attenuates hypertrophic and profibrotic gene expression in rodent models of HCM <Reference id=40621/>.
iupac name: 6-[[(1S)-1-phenylethyl]amino]-3-propan-2-yl-1H-pyrimidine-2,4-dione
xref: CHEMBL4297517
synonym: MYK-461
synonym: MYK461
synonym: Camzyos®
approved: t
ligand name: mavacamten
type: SyntheticOrganicLigand

PSB-16434
canonical SMILES: Clc1ccc(cc1)CCNc1cc(=O)[nH]c(=O)[nH]1
isomeric SMILES: Clc1ccc(cc1)CCNc1cc(=O)[nH]c(=O)[nH]1
in ch i key: JSUODDTVALGQAK-UHFFFAOYSA-N
in ch i: InChI=1S/C12H12ClN3O2/c13-9-3-1-8(2-4-9)5-6-14-10-7-11(17)16-12(18)15-10/h1-4,7H,5-6H2,(H3,14,15,16,17,18)
comment: Orthosteric agonist of GPR84.
iupac name: 6-[2-(4-chlorophenyl)ethylamino]-1H-pyrimidine-2,4-dione
approved: f
ligand name: PSB-16434
type: SyntheticOrganicLigand

enoxolone
in ch i key: MPDGHEJMBKOTSU-YKLVYJNSSA-N
in ch i: InChI=1S/C30H46O4/c1-25(2)21-8-11-30(7)23(28(21,5)10-9-22(25)32)20(31)16-18-19-17-27(4,24(33)34)13-12-26(19,3)14-15-29(18,30)6/h16,19,21-23,32H,8-15,17H2,1-7H3,(H,33,34)/t19-,21-,22-,23+,26+,27-,28-,29+,30+/m0/s1
comment: Enoxolone is a bioactive metabolite of glycyrrhizin, which is a compound found in the liquorice plant Glycyrrhiza glabra. It has been found to inhibit enzymes that metabolise the prostaglandins PGE2 and PGF2α to their inactive metabolites, and 11β-hydroxysteroid dehydrogenases (HSD11B1, HSD11B2) which convert active cortisol to inactive cortisone. Enoxolone has proposed anti-inflammatory <Reference id=40610/><Reference id=40607/><Reference id=40609/><Reference id=40608/> and antitussive effects as well as action against pathogens (viruses, fungal infections, bacterial infections) <Reference id=40605/><Reference id=40606/>, and beneficial actions for the treatmant of gastric ulcers.
xref: CHEMBL230006
synonym: 18β-Glycyrrhetinic acid
synonym: glycyrrhetinic acid
synonym: glycyrrhetic acid
approved: f
ligand name: enoxolone
type: SyntheticOrganicLigand

compound 11c [PMID: 30613327]
in ch i key: CJKMEXVEIKDLMA-UHFFFAOYSA-N
in ch i: InChI=1S/C22H18F3N3O3/c1-13-20(27-19-9-17(30-2)7-8-18(19)21(13)29)15-10-26-28(12-15)11-14-3-5-16(6-4-14)31-22(23,24)25/h3-10,12H,11H2,1-2H3,(H,27,29)
comment: Compound 11c has been identified as a representative analogue for the 2-pyrazolyl quinolone series of antimalarial compounds <Reference id=40647/>. The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
iupac name: 7-methoxy-3-methyl-2-[1-[[4-(trifluoromethoxy)phenyl]methyl]pyrazol-4-yl]-1H-quinolin-4-one
approved: f
ligand name: compound 11c [PMID: 30613327]
type: SyntheticOrganicLigand

AM-37
in ch i key: INNVRNIOVHJSQS-MUUNZHRXSA-N
in ch i: InChI=1S/C31H35N5O3/c1-39-25-13-11-24(12-14-25)35-30(38)36-28(18-22-19-33-27-10-4-3-9-26(22)27)29(37)34-21-31(15-5-2-6-16-31)23-8-7-17-32-20-23/h3-4,7-14,17,19-20,28,33H,2,5-6,15-16,18,21H2,1H3,(H,34,37)(H2,35,36,38)/t28-/m1/s1
comment: AM-37 and its S-enantiomer, ST-36 (PubChem CID 122181320), are non-peptide BB3 receptor antagonists <Reference id=40548/>.
iupac name: (2R)-3-(1H-indol-3-yl)-2-[(4-methoxyphenyl)carbamoylamino]-N-[(1-pyridin-3-ylcyclohexyl)methyl]propanamide
xref: CHEMBL3590072
approved: f
ligand name: AM-37
type: SyntheticOrganicLigand

compound A [PMID: 28324017]
in ch i key: KERMKRMLWZLZAK-UHFFFAOYSA-N
in ch i: InChI=1S/C27H28N2O3/c1-27(2,3)28-25(30)24-22-13-9-8-12-20(22)21-15-14-19(32-4)16-23(21)26(31)29(24)17-18-10-6-5-7-11-18/h5-16,24H,17H2,1-4H3,(H,28,30)
comment: Compound A is a small molecule agonist of BB3 receptor <Reference id=40544/>. It was found to promote weight loss in a rat model of diet-induced obesity.
approved: f
ligand name: compound A [PMID: 28324017]
type: SyntheticOrganicLigand

[Leu14]bombesin
in ch i key: SVVDBCGUBZWHSS-FPFNSDSHSA-N
comment: This is a modified version of endogenous bombesin <Reference id=20720/>.
approved: f
ligand name: [Leu14]bombesin
type: PeptideLigand

decanoyl-RVKR-chloromethylketone
in ch i key: NHBJTTGFHCHQHS-VZTVMPNDSA-N
comment: Decanoyl-RVKR-CMK is a cell‐permeable and irreversible inhibitor of proprotein convertase (PC) enzymes <Reference id=40483/>. The PC family of serine proteases includes furin. Furin-mediated cleavage of HIV-1 envelope glycoprotein 160 (gp160) is essential for fusion of the viral envelope with the host cell membrane <Reference id=40483/>. SARS-CoV-2: Decanoyl-RVKR-CMK inhibits cleavage of SARS-CoV-2 spike protein by furin, at the furin cleavage site, and this translates to an antiviral effect in vitro <Reference id=40482/>.
synonym: Decanoyl-RVKR-CMK
synonym: decanoyl-Arg-Val-Lys-Arg-CMK
approved: f
ligand name: decanoyl-RVKR-chloromethylketone
type: SyntheticOrganicLigand

Z-FA-FMK
in ch i key: ASXVEBPEZMSPHB-PKHIMPSTSA-N
in ch i: InChI=1S/C21H23FN2O4/c1-15(19(25)13-22)23-20(26)18(12-16-8-4-2-5-9-16)24-21(27)28-14-17-10-6-3-7-11-17/h2-11,15,18H,12-14H2,1H3,(H,23,26)(H,24,27)/t15?,18-/m0/s1
comment: Z-FA-FMK is a modified di-peptide. It has been reported as a cathepsin B inhibtor <Reference id=40463/>, and antiviral activity against a variety of viruses has been reported <Reference id=40462/>. SARS-CoV-2: In an HTS screening programme Z-FA-FMK was found to inhibit the 3CL protease (Mpro) of SARS-CoV-2 <Reference id=40461/>. This inhibition translated to an antiviral effect with an EC50 of 130 nM.
iupac name: benzyl N-[(2S)-1-[(4-fluoro-3-oxobutan-2-yl)amino]-1-oxo-3-phenylpropan-2-yl]carbamate
xref: CHEMBL54797
synonym: Z-Phe-DL-Ala-fluoromethylketone
synonym: MDL 201053
synonym: MDL201053
synonym: MDL-201053
synonym: ZFA-fmk
approved: f
ligand name: Z-FA-FMK
type: PeptideLigand

walrycin B
in ch i key: XRVMPTWWKLKLPB-UHFFFAOYSA-N
in ch i: InChI=1S/C14H10F3N5O2/c1-21-12(23)9-11(19-13(21)24)22(2)20-10(18-9)7-3-5-8(6-4-7)14(15,16)17/h3-6H,1-2H3
comment: Walrycin B is an antibacterial that has activity against Gram-positive bacteria (including Bacillus subtilis and Staphylococcus aureus), by inhibiting WalR, a response regulator that is essential for bacterial viability <Reference id=40460/>. SARS-CoV-2: In an HTS screening programme walrycin B was found to inhibit the 3CL protease (Mpro) of SARS-CoV-2 <Reference id=40461/>. This inhibition translated to an antiviral effect with an EC50 of 3.6 μM.
xref: CHEMBL1096283
approved: f
ligand name: walrycin B
type: SyntheticOrganicLigand

HTI-1
in ch i key: PHDIJLFSKNMCMI-ITGJKDDRSA-N
in ch i: InChI=1S/C23H33NO7/c25-15-19-20(26)22(21(27)23(28)31-19)30-13-6-4-2-1-3-5-12-29-17-9-10-18-16(14-17)8-7-11-24-18/h7-11,14,19-23,25-28H,1-6,12-13,15H2/t19-,20-,21-,22+,23?/m1/s1
comment: HTI-1 is a derivative of the glucose analogue C3361, with improved inhibition of the Plasmodium hexose transporter (PfHT1) <Reference id=40465/>. The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
iupac name: (3R,4S,5R,6R)-6-(hydroxymethyl)-4-(8-quinolin-6-yloxyoctoxy)oxane-2,3,5-triol
synonym: compound 1c
approved: f
ligand name: HTI-1
type: SyntheticOrganicLigand

AX-024
in ch i key: VMMKGVRPILDZML-UHFFFAOYSA-N
in ch i: InChI=1S/C21H22FNO2/c1-24-18-8-9-20-19(12-18)21(15-4-6-17(22)7-5-15)16(14-25-20)13-23-10-2-3-11-23/h4-9,12H,2-3,10-11,13-14H2,1H3
comment: AX-024 is a novel T cell modulator, that acts by disrupting the protein-protein interaction between CD3ε (a subunit in the T-cell receptor, TCR) and Nck, which causes a conformational change that prevents TCR activation <Reference id=40452/><Reference id=40453/>. It was developed by Artax Biopharma and seems to be a predecessor of their autoimmune clinical lead AX-158 (structure not disclosed).
synonym: AX024
synonym: AX-24
approved: f
ligand name: AX-024
type: SyntheticOrganicLigand

C3a receptor agonist
in ch i key: RMFOYNMWESQGBZ-UHFFFAOYSA-N
in ch i: InChI=1S/C27H35N3O2/c31-25(14-13-21-8-7-17-28-20-21)30-18-15-24(16-19-30)29-27(32)26(22-9-3-1-4-10-22)23-11-5-2-6-12-23/h1,3-4,7-10,17,20,23-24,26H,2,5-6,11-16,18-19H2,(H,29,32)
comment: This compound is a non-arginine C3aR agonist <Reference id=40439/>.
iupac name: 2-cyclohexyl-2-phenyl-N-[1-(3-pyridin-3-ylpropanoyl)piperidin-4-yl]acetamide
synonym: compound 7 [PMID: 17459702]
approved: f
ligand name: C3a receptor agonist
type: SyntheticOrganicLigand

6-nonylpyridine-2,4-diol
canonical SMILES: CCCCCCCCCc1cc(O)cc(=O)[nH]1
isomeric SMILES: CCCCCCCCCc1cc(O)cc(=O)[nH]1
in ch i key: JCINCSYDDSRQQC-UHFFFAOYSA-N
in ch i: InChI=1S/C14H23NO2/c1-2-3-4-5-6-7-8-9-12-10-13(16)11-14(17)15-12/h10-11H,2-9H2,1H3,(H2,15,16,17)
comment: Orthosteric agonist of GPR84.
iupac name: 4-hydroxy-6-nonyl-1H-pyridin-2-one
approved: f
ligand name: 6-nonylpyridine-2,4-diol
type: SyntheticOrganicLigand

PF-00835231
in ch i key: QDIMHKWNHMVDJB-WBAXXEDZSA-N
in ch i: InChI=1S/C24H32N4O6/c1-13(2)9-18(23(32)27-17(20(30)12-29)10-14-7-8-25-22(14)31)28-24(33)19-11-15-16(26-19)5-4-6-21(15)34-3/h4-6,11,13-14,17-18,26,29H,7-10,12H2,1-3H3,(H,25,31)(H,27,32)(H,28,33)/t14-,17-,18-/m0/s1
comment: PF-00835231 was designed to inhibit the 3CL protease (Mpro) of SARS-CoV-1, and has efficacy against a range of 3CLpro from α-, β-, and γ-coronaviruses <Reference id=40433/><Reference id=41363/>. It is the active metabolite of the more soluble phosphate analogue <Ligand id=11249/> (PF-07304814). The pharmaceutical properties make both compounds suitable for intravenous infusion.
iupac name: (2S)-N-[(2S)-4-hydroxy-3-oxo-1-[(3S)-2-oxopyrrolidin-3-yl]butan-2-yl]-2-[(4-methoxy-1H-indol-2-yl)formamido]-4-methylpentanamide
synonym: compound 4 [Hoffman et al., 2020]
synonym: PF-0835231
approved: f
ligand name: PF-00835231
type: SyntheticOrganicLigand

lufotrelvir
in ch i key: FQKALOFOWPDTED-WBAXXEDZSA-N
in ch i: InChI=1S/C24H33N4O9P/c1-13(2)9-18(28-24(32)19-11-15-16(26-19)5-4-6-21(15)36-3)23(31)27-17(10-14-7-8-25-22(14)30)20(29)12-37-38(33,34)35/h4-6,11,13-14,17-18,26H,7-10,12H2,1-3H3,(H,25,30)(H,27,31)(H,28,32)(H2,33,34,35)/t14-,17-,18-/m0/s1
comment: PF-07304814 is a SARS-CoV-2 3CL protease (Mpro) inhibitor from Pfizer. The structure of PF-07304814 is identical to that of the INN lufotrelvir (from proposed list 125, July 2021). PF-07304814's phosphate group (which improves solubility) is cleaved in vitro to release the active antiviral PF-00835231 <Reference id=40432/><Reference id=42715/>. PF-00835231 was originally developed as a SARS-CoV Mpro inhibitor in response to the 2002-2003 outbreak <Reference id=40433/>. Like <Ligand id=10715/>, PF-07304814 is administered by intravenous infusion.
iupac name: [(3S)-3-[(2S)-2-[(4-methoxy-1H-indol-2-yl)formamido]-4-methylpentanamido]-2-oxo-4-[(3S)-2-oxopyrrolidin-3-yl]butoxy]phosphonic acid
synonym: PF-07304814
synonym: PF07304814
approved: f
ligand name: lufotrelvir
type: SyntheticOrganicLigand

hypericin
in ch i key: YDOIFHVUBCIUHF-UHFFFAOYSA-N
in ch i: InChI=1S/C30H16O8/c1-7-3-9(31)19-23-15(7)16-8(2)4-10(32)20-24(16)28-26-18(12(34)6-14(36)22(26)30(20)38)17-11(33)5-13(35)21(29(19)37)25(17)27(23)28/h3-6,33-38H,1-2H3
comment: Hypericin is one of the active ingredients of St John's wort. It's pharmacological activity is complex and not fully resolved.
approved: f
ligand name: hypericin
type: NaturalProductLigand

opipramol
canonical SMILES: OCCN1CCN(CC1)CCCN1c2ccccc2C=Cc2c1cccc2
isomeric SMILES: OCCN1CCN(CC1)CCCN1c2ccccc2C=Cc2c1cccc2
in ch i key: YNZFUWZUGRBMHL-UHFFFAOYSA-N
in ch i: InChI=1S/C23H29N3O/c27-19-18-25-16-14-24(15-17-25)12-5-13-26-22-8-3-1-6-20(22)10-11-21-7-2-4-9-23(21)26/h1-4,6-11,27H,5,12-19H2
comment: Opipramol is an atypical tricyclic antidepressant (TCA) <Reference id=40426/>. It acts primarily as a sigma (σ) receptor agonist. Weak antiviral activity of opipramol dihydrochloride against SARS-CoV-2 (in Vero E6 cells; EC50 5 μM) was reported by Touret et al. <Reference id=40428/>.
iupac name: 2-[4-(3-benzo[b][1]benzazepin-11-ylpropyl)piperazin-1-yl]ethanol
xref: CHEMBL370753
synonym: Insidon®
approved: t
ligand name: opipramol
type: SyntheticOrganicLigand

gestodene
in ch i key: SIGSPDASOTUPFS-XUDSTZEESA-N
in ch i: InChI=1S/C21H26O2/c1-3-20-11-9-17-16-8-6-15(22)13-14(16)5-7-18(17)19(20)10-12-21(20,23)4-2/h2,10,12-13,16-19,23H,3,5-9,11H2,1H3/t16-,17+,18+,19-,20-,21-/m0/s1
comment: Gestodene is a progestin that is present in combined oral contraceptives and hormone replacement therapies used to manage menopausal symptoms.
xref: CHEMBL1213583
synonym: Femodene® (ethinylestradiol, gestodene)
synonym: Millinette® (ethinylestradiol, gestodene)
synonym: SH-B-331
approved: t
ligand name: gestodene
type: SyntheticOrganicLigand

nomegestrol
in ch i key: KZUIYQJTUIACIG-YBZCJVABSA-N
in ch i: InChI=1S/C21H28O3/c1-12-10-18-16(15-5-4-14(23)11-17(12)15)6-8-20(3)19(18)7-9-21(20,24)13(2)22/h10-11,15-16,18-19,24H,4-9H2,1-3H3/t15-,16-,18-,19+,20+,21+/m1/s1
comment: Nomegestrol (as the acetate) is a progestin that is used in hormonal medications and oral contraceptives.
xref: CHEMBL2105722
approved: t
ligand name: nomegestrol
type: SyntheticOrganicLigand

emtricitabine
canonical SMILES: Nc1nc(=O)n(cc1F)[C@@H]1CS[C@@H](O1)CO
isomeric SMILES: Nc1nc(=O)n(cc1F)[C@@H]1CS[C@@H](O1)CO
in ch i key: XQSPYNMVSIKCOC-NTSWFWBYSA-N
in ch i: InChI=1S/C8H10FN3O3S/c9-4-1-12(8(14)11-7(4)10)5-3-16-6(2-13)15-5/h1,5-6,13H,2-3H2,(H2,10,11,14)/t5-,6+/m0/s1
comment: Emtricitabine is a nucleoside reverse transcriptase inhibitor (NRTI) antiretroviral compound.
iupac name: 4-amino-5-fluoro-1-[(2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]pyrimidin-2-one
xref: CHEMBL885
synonym: BW-524W91
synonym: 524W91
synonym: Emtriva®
synonym: Coviracil®
approved: t
ligand name: emtricitabine
type: SyntheticOrganicLigand

darunavir
in ch i key: CJBJHOAVZSMMDJ-HEXNFIEUSA-N
in ch i: InChI=1S/C27H37N3O7S/c1-18(2)15-30(38(33,34)21-10-8-20(28)9-11-21)16-24(31)23(14-19-6-4-3-5-7-19)29-27(32)37-25-17-36-26-22(25)12-13-35-26/h3-11,18,22-26,31H,12-17,28H2,1-2H3,(H,29,32)/t22-,23-,24+,25-,26+/m0/s1
comment: Darunavir is a second-generation human immunodeficiency virus 1 (HIV-1) protease inhibitor (PI) <Reference id=40424/>.
iupac name: [(3R,3aS,6aR)-2,3,3a,4,5,6a-hexahydrofuro[5,4-b]furan-3-yl] N-[(2S,3R)-4-[(4-aminophenyl)sulfonyl-(2-methylpropyl)amino]-3-hydroxy-1-phenylbutan-2-yl]carbamate
xref: CHEMBL1323
synonym: TMC114
synonym: UIC-94017
synonym: Prezista®
synonym: TMC-114
approved: t
ligand name: darunavir
type: SyntheticOrganicLigand

BI01383298
in ch i key: VUOYAALVGSMUHC-UHFFFAOYSA-N
comment: BI01383298 is a highly potent and selective human sodium-coupled citrate transporter SLC13A5 inhibitor that was developed by Boehringer Ingelheim <Reference id=40423/>. It is structurally distinct from SLC13A5's substrate, citrate. BI01383298 is available free-of-charge through Boehringer's opnMe programme or from the Structural Genomics Consortium. This inhibitor is suitable for in vitro experiments.
iupac name: 1-(3,5-dichlorophenyl)sulfonyl-N-[(4-fluorophenyl)methyl]piperidine-4-carboxamide
synonym: BI-01383298
approved: f
ligand name: BI01383298
type: SyntheticOrganicLigand

terlipressin
in ch i key: BENFXAYNYRLAIU-QSVFAHTRSA-N
comment: Terlipressin is a clinically used vasopressin analogue. Terlipressin is biotransformed to its active moiety, lysine vasopressin (LVP). It has vasoconstrictive, antihemorrhagic, and antidiuretic properties.
xref: CHEMBL2135460
synonym: N-(N-(N-Glycylglycyl)glycyl)-8-L-lysinevasopressin
synonym: Variquel®
synonym: Glypressin®
synonym: glycyl-glycyl-glycyl-L-cysteinyl-L-tyrosyl-L-phenylalanyl-L-glutaminyl-L-asparagyl-L-cysteinyl-L-prolyl-L-lysyl-glycinamide (4->9)-disulfide
synonym: Terlivaz®
approved: t
ligand name: terlipressin
type: PeptideLigand

NSC600684
in ch i key: XYYIYKRFSGVWQQ-UHFFFAOYSA-N
in ch i: InChI=1S/C28H31N5O2/c1-20(2)21-8-10-25-24(18-21)28(35)33-19-22(9-11-26(33)30-25)27(34)29-12-13-31-14-16-32(17-15-31)23-6-4-3-5-7-23/h3-11,18-20H,12-17H2,1-2H3,(H,29,34)
comment: NSC600684 is a TRPV4 antagonist. We show the structure for the parent molecule, but it is used experimentally in its hydrochloride salt form (PubChem CID: 45260031).
iupac name: 11-oxo-N-[2-(4-phenylpiperazin-1-yl)ethyl]-2-propan-2-ylpyrido[2,1-b]quinazoline-8-carboxamide
xref: CHEMBL1192118
synonym: NSC-600684
approved: f
ligand name: NSC600684
type: SyntheticOrganicLigand

NSC212069
in ch i key: BJJNHDXKMSVOMG-UHFFFAOYSA-O
comment: NSC212069 is a TRPV4 antagonist. We show the structure for the parent molecule, but it is used experimentally in its hydrochloride salt form (PubChem CID: 24196249).
iupac name: 2-(3,4-dichlorophenoxy)-N-[1-[(3,4-dichlorophenyl)methyl]pyridin-1-ium-3-yl]acetamide
synonym: NSC-212069
approved: f
ligand name: NSC212069
type: SyntheticOrganicLigand

NSC151066
in ch i key: YXFFXVOWPKYLNW-UHFFFAOYSA-O
in ch i: InChI=1S/C20H19F6N3O2/c1-29(2,11-17(30)27-15-7-3-5-13(9-15)19(21,22)23)12-18(31)28-16-8-4-6-14(10-16)20(24,25)26/h3-10H,11-12H2,1-2H3,(H-,27,28,30,31)/p+1
comment: NSC151066 is a TRPV4 antagonist. We show the structure for the parent molecule, but it is used experimentally in its hydrochloride salt form (PubChem CID: 4193327).
iupac name: dimethyl-bis[2-oxo-2-[3-(trifluoromethyl)anilino]ethyl]azanium
synonym: NSC-151066
approved: f
ligand name: NSC151066
type: SyntheticOrganicLigand

LCB3
in ch i key: AYKCULXVFGARTK-NUIKKLCPSA-N
comment: A synthetic peptide that binds potently to the ACE2 binding domain of the SARS-CoV-2 spike protein, and blocks entry of SARS-CoV-2 in vitro <Reference id=40468/>. The chemical SMILES was generated using the HELM editor. The crystal structure of LCB3 in complex with SARS-CoV-2 spike protein has been deposited with the PDB, ID 7JZN
approved: f
ligand name: LCB3
type: PeptideLigand

LCB1
in ch i key: NDMHMGNPFJKEIS-HNVXLNGZSA-N
comment: A synthetic peptide that binds potently to the ACE2 binding domain of the SARS-CoV-2 spike protein, and blocks entry of SARS-CoV-2 in vitro. The peptide sequence was obtained from supplementary table S2 in the original article <Reference id=40468/>. The chemical SMILES was generated using the HELM editor. Note that the peptide in the PDB crystal complex with SARS-CoV-2 spike is shorter by one amino acid (missing the Arg at the COOH terminal) than the sequence we show here - see 7JZL .
approved: f
ligand name: LCB1
type: PeptideLigand

compound 46 [PMID: 25268943]
in ch i key: SCPYAGLHLAAYFP-UHFFFAOYSA-N
in ch i: InChI=1S/C22H30N6O/c23-21(24)26-14-13-25-20(29)22(27-19-9-5-2-6-10-19)11-15-28(16-12-22)17-18-7-3-1-4-8-18/h1-10,27H,11-17H2,(H,25,29)(H4,23,24,26)
comment: Compound 46 is a non-peptidic antagonist of the neuropeptide FF1 receptor <Reference id=40410/>. It has low binding affinity for opioid receptors.
xref: CHEMBL3361425
approved: f
ligand name: compound 46 [PMID: 25268943]
type: SyntheticOrganicLigand

oxidised ATP
in ch i key: ZOSTZYMLOPBGQI-NKWVEPMBSA-N
iupac name: [[(2R)-2-[(1R)-1-(6-aminopurin-9-yl)-2-oxoethoxy]-3-oxopropoxy]-hydroxyphosphoryl] phosphono hydrogen phosphate
xref: CHEMBL4285222
synonym: oxo-ATP
synonym: 2',3'-dialdehyde ATP
synonym: ATP dialdehyde
synonym: oATP
approved: f
ligand name: oxidised ATP
type: SyntheticOrganicLigand

NP-1815-PX
in ch i key: BNMITFGQPNUZHK-UHFFFAOYSA-N
in ch i: InChI=1S/C21H14N4O3S/c26-17-11-18(27)25(14-6-3-5-13(10-14)20-23-21(29)28-24-20)16-9-8-12-4-1-2-7-15(12)19(16)22-17/h1-10H,11H2,(H,22,26)(H,23,24,29)
comment: NP-1815-PX is a P2X4 antagonist <Reference id=40405/>.
iupac name: 5-[3-(5-sulfanylidene-2H-1,2,4-oxadiazol-3-yl)phenyl]-1H-benzo[g][1,5]benzodiazepine-2,4-dione
approved: f
ligand name: NP-1815-PX
type: SyntheticOrganicLigand

BLU-5937
in ch i key: HHJIZLMOCIYWJF-HNNXBMFYSA-N
in ch i: InChI=1S/C24H26F2N4O3/c1-14-6-8-30-19(10-15-5-4-7-29(13-15)24(32)33-3)22(28-20(30)9-14)21-17(25)11-16(12-18(21)26)23(31)27-2/h6,8-9,11-12,15H,4-5,7,10,13H2,1-3H3,(H,27,31)/t15-/m0/s1
comment: BLU-5937 is a clinical stage selective P2X3 antagonist <Reference id=40404/>. It is being developed by Bellus, as a competitor to Merck's P2X3 inhibitor <Ligand id=9540/>.
synonym: P2X3 antagonist 34
synonym: BLU5937
synonym: NEO5937
approved: f
ligand name: BLU-5937
type: SyntheticOrganicLigand

MRS2159
in ch i key: NPBWMMRUXMTIRC-UHFFFAOYSA-N
in ch i: InChI=1S/C15H14N3O8P/c1-8-13(20)11(6-19)12(7-26-27(23,24)25)14(16-8)18-17-10-4-2-9(3-5-10)15(21)22/h2-6,20H,7H2,1H3,(H,21,22)(H2,23,24,25)
comment: MRS2159 is a P2X1 receptor antagonist <Reference id=40402/>.
iupac name: 4-[[4-formyl-5-hydroxy-6-methyl-3-(phosphonooxymethyl)pyridin-2-yl]diazenyl]benzoic acid
xref: CHEMBL119235
synonym: MRS-2159
approved: f
ligand name: MRS2159
type: SyntheticOrganicLigand

compound 6e [PMID: 32747425]
in ch i key: FOLCUFKJHSQMEL-BIXPGCQOSA-N
in ch i: InChI=1S/C24H41N3O5/c1-4-5-6-17-7-9-20(10-8-17)32-24(31)27-21(13-16(2)3)23(30)26-19(15-28)14-18-11-12-25-22(18)29/h15-21H,4-14H2,1-3H3,(H,25,29)(H,26,30)(H,27,31)/t17?,18-,19-,20?,21-/m0/s1
comment: Compound 6e is reported as an inhibitor of the 3CL proteinases (3CLpro) from MERS, SARS-CoV and SARS-CoV-2 coronaviruses <Reference id=40311/>.
iupac name: 4-butylcyclohexyl N-[(1S)-3-methyl-1-{[(2S)-1-oxo-3-[(3S)-2-oxopyrrolidin-3-yl]propan-2-yl]carbamoyl}butyl]carbamate
approved: f
ligand name: compound 6e [PMID: 32747425]
type: SyntheticOrganicLigand

FUB 465
canonical SMILES: CCOCCCc1cnc[nH]1
isomeric SMILES: CCOCCCc1cnc[nH]1
in ch i key: RSHKAUMLIJVWFJ-UHFFFAOYSA-N
in ch i: InChI=1S/C8H14N2O/c1-2-11-5-3-4-8-6-9-7-10-8/h6-7H,2-5H2,1H3,(H,9,10)
iupac name: 4-(3-ethoxypropyl)-3H-imidazole
xref: CHEMBL1184024
synonym: FUB-465
synonym: FUB465
approved: f
ligand name: FUB 465
type: SyntheticOrganicLigand

clascoterone
in ch i key: GPNHMOZDMYNCPO-PDUMRIMRSA-N
in ch i: InChI=1S/C24H34O5/c1-4-21(28)29-24(20(27)14-25)12-9-19-17-6-5-15-13-16(26)7-10-22(15,2)18(17)8-11-23(19,24)3/h13,17-19,25H,4-12,14H2,1-3H3/t17-,18+,19+,22+,23+,24+/m1/s1
comment: Clascoterone is a steroidal androgen receptor antagonist (antiandrogen) <Reference id=40310/>. It was developed to address the hormonal pathogenesis of acne <Reference id=40307/>. It has been shown to inhibit production of lipids and inflammatory cytokines from sebocytes <Reference id=40308/>.
iupac name: [(8R,9S,10R,13S,14S,17R)-17-(2-hydroxyacetyl)-10,13-dimethyl-3-oxo-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-17-yl] propanoate
xref: CHEMBL3590187
synonym: CB-03-01
synonym: Winlevi®
synonym: cortexolone 17α-propionate
synonym: CB-0301
approved: t
ligand name: clascoterone
type: SyntheticOrganicLigand

compound 3 [PMID: 32258933]
canonical SMILES: Clc1ccc2c(c1)nc(n2Cc1ccccc1)N1CCNCC1
isomeric SMILES: Clc1ccc2c(c1)nc(n2Cc1ccccc1)N1CCNCC1
in ch i key: RDAXAGXJSCEYLT-UHFFFAOYSA-N
in ch i: InChI=1S/C18H19ClN4/c19-15-6-7-17-16(12-15)21-18(22-10-8-20-9-11-22)23(17)13-14-4-2-1-3-5-14/h1-7,12,20H,8-11,13H2
comment: Compound 3 is the lead for a novel series of antimalarial compounds based on a benzimidazole core <Reference id=40299/>. The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
iupac name: 5-chloro-1-(phenylmethyl)-2-piperazin-1-ylbenzimidazole
xref: CHEMBL294083
approved: f
ligand name: compound 3 [PMID: 32258933]
type: SyntheticOrganicLigand

Embelin
canonical SMILES: CCCCCCCCCCCC1=C(O)C(=O)C=C(C1=O)O
isomeric SMILES: CCCCCCCCCCCC1=C(O)C(=O)C=C(C1=O)O
in ch i key: IRSFLDGTOHBADP-UHFFFAOYSA-N
in ch i: InChI=1S/C17H26O4/c1-2-3-4-5-6-7-8-9-10-11-13-16(20)14(18)12-15(19)17(13)21/h12,18,21H,2-11H2,1H3
comment: Orthosteric agonist of GPR84.
iupac name: 2,5-dihydroxy-3-undecylcyclohexa-2,5-diene-1,4-dione
approved: f
ligand name: Embelin
type: NaturalProductLigand

NF279
in ch i key: VNPQLQQGQYADEZ-UHFFFAOYSA-N
comment: NF279 is a suramin analogue antagonist of human P2X1 and P2X7 receptors, with some selectivity for P2X1 <Reference id=40401/>. It may be used experimentally as the hexasodium salt.
iupac name: 8-[[4-[[4-[[4-[[4-[(4,6,8-trisulfonaphthalen-1-yl)carbamoyl]phenyl]carbamoyl]phenyl]carbamoylamino]benzoyl]amino]benzoyl]amino]naphthalene-1,3,5-trisulfonic acid
approved: f
ligand name: NF279
type: SyntheticOrganicLigand

inhibitor CB3
canonical SMILES: Clc1ccc(c(c1)C(F)(F)F)NC(=O)c1nocc1
isomeric SMILES: Clc1ccc(c(c1)C(F)(F)F)NC(=O)c1nocc1
in ch i key: COZVUVXNGYGPKO-UHFFFAOYSA-N
comment: CB3 is reported as a novel inhibitor of the neutral amino acid transporter B0AT1 (SLC6A19) <Reference id=40400/>.
iupac name: N-[4-chloro-2-(trifluoromethyl)phenyl]-1,2-oxazole-3-carboxamide
approved: f
ligand name: inhibitor CB3
type: SyntheticOrganicLigand

inhibitor E18
canonical SMILES: COc1ccccc1Nc1nc2c(s1)cccc2
isomeric SMILES: COc1ccccc1Nc1nc2c(s1)cccc2
in ch i key: OAXDBPDAUUFQFJ-UHFFFAOYSA-N
in ch i: InChI=1S/C14H12N2OS/c1-17-12-8-4-2-6-10(12)15-14-16-11-7-3-5-9-13(11)18-14/h2-9H,1H3,(H,15,16)
comment: E18 is reported as a novel inhibitor of the neutral amino acid transporter B0AT1 (SLC6A19) <Reference id=40400/>.
iupac name: N-(2-methoxyphenyl)-1,3-benzothiazol-2-amine
approved: f
ligand name: inhibitor E18
type: SyntheticOrganicLigand

inhibitor E4
canonical SMILES: CC(NC(=O)COc1c(C)cc(cc1C)Cl)C
isomeric SMILES: CC(NC(=O)COc1c(C)cc(cc1C)Cl)C
in ch i key: GMPVHSCTBWUYRE-UHFFFAOYSA-N
in ch i: InChI=1S/C13H18ClNO2/c1-8(2)15-12(16)7-17-13-9(3)5-11(14)6-10(13)4/h5-6,8H,7H2,1-4H3,(H,15,16)
comment: E4 is reported as a novel inhibitor of the neutral amino acid transporter B0AT1 (SLC6A19) <Reference id=40400/>.
iupac name: 2-(4-chloro-2,6-dimethylphenoxy)-N-propan-2-ylacetamide
approved: f
ligand name: inhibitor E4
type: SyntheticOrganicLigand

NPS(1-4)NH2
in ch i key: VWBPRJXOZDIUPZ-VGWMRTNUSA-N
in ch i: InChI=1S/C22H35N9O6/c23-13(11-32)19(35)31-16(9-12-5-2-1-3-6-12)21(37)29-14(7-4-8-28-22(26)27)20(36)30-15(18(25)34)10-17(24)33/h1-3,5-6,13-16,32H,4,7-11,23H2,(H2,24,33)(H2,25,34)(H,29,37)(H,30,36)(H,31,35)(H4,26,27,28)/t13-,14-,15-,16-/m0/s1
comment: This is a tetrapeptide truncation of human neuropeptide S (NPS) <Reference id=40385/>. It exhibits agonist bias for calcium mobilisation compared to cAMP accumulation in vitro. HELM annotation is PEPTIDE1{S.F.R.N.[am]}$$$$.
synonym: PEPTIDE1{S.F.R.N.[am]}$$$$
synonym: peptide 3 [PMID: 28267583]
approved: f
ligand name: NPS(1-4)NH2
type: PeptideLigand

compound 4 [PMID: 32677155]
in ch i key: YNSHZGLASDJCCG-SANMLTNESA-N
in ch i: InChI=1S/C33H29F6N3O4/c1-20-29(22-10-5-13-27(30(22)36)46-17-15-34)31(44)42(19-26(21-8-3-2-4-9-21)40-16-7-14-28(40)43)32(45)41(20)18-23-24(33(37,38)39)11-6-12-25(23)35/h2-6,8-13,26H,7,14-19H2,1H3/t26-/m0/s1
comment: Compound 4 is a small molecule GnRH receptor antagonist <Reference id=40344/>. It was designed to be labelled with fluorine-18 and used as a PET tracer for brain imaging in animal experiments. This antagonist is brain-penetrating and accumulates at GnRH receptor specific sites in the brain.
synonym: [18F]4
approved: f
ligand name: compound 4 [PMID: 32677155]
type: SyntheticOrganicLigand

BAY-545
in ch i key: NTYVAKNEYLJAPT-UHFFFAOYSA-N
comment: BAY-545 is an A2B receptor antagonist that is suitable for use in vivo <Reference id=40340/>.
iupac name: 3-ethyl-6-(4-hydroxypiperidine-1-carbonyl)-5-methyl-1-(3,3,3-trifluoropropyl)thieno[2,3-d]pyrimidine-2,4-dione
synonym: compound 8 [PMID: 30576906]
synonym: BAY545
approved: f
ligand name: BAY-545
type: SyntheticOrganicLigand

ISAM-140
in ch i key: NYHLRBMDXQBOIB-UHFFFAOYSA-N
in ch i: InChI=1S/C19H19N3O3/c1-11(2)25-18(23)16-12(3)20-19-21-13-7-4-5-8-14(13)22(19)17(16)15-9-6-10-24-15/h4-11,17H,1-3H3,(H,20,21)
comment: ISAM-140 is an adenosine 2B receptor antagonist <Reference id=40339/>.
iupac name: propan-2-yl 4-(furan-2-yl)-2-methyl-1,4-dihydropyrimido[1,2-a]benzimidazole-3-carboxylate
xref: CHEMBL3787197
synonym: compound 22b [PMID: 26824742]
synonym: ISAM140
approved: f
ligand name: ISAM-140
type: SyntheticOrganicLigand

neladenoson
canonical SMILES: OCCOc1ccc(cc1)c1c(C#N)c(SCc2csc(n2)c2ccc(cc2)Cl)nc(c1C#N)N1CCCC1
isomeric SMILES: OCCOc1ccc(cc1)c1c(C#N)c(SCc2csc(n2)c2ccc(cc2)Cl)nc(c1C#N)N1CCCC1
in ch i key: RFJKJKQQWXKVTD-UHFFFAOYSA-N
comment: Neladenoson is a partial adenosine A1 receptor agonist <Reference id=40334/>. It is administered as a dipeptide ester to improve solubility and exposure after oral administration and the INN refers to the prodrug structure, neladenoson bialanate. We show the parent molecule in this entry. Neladenoson was the first-in-class adenosine A1 receptor partial agonist to enter clinical evaluation for the treatment of heart failure <Reference id=40335/>.
iupac name: 2-({[2-(4-chlorophenyl)-1,3-thiazol-4-yl]methyl}sulfanyl)-4-[4-(2-hydroxyethoxy)phenyl]-6-(pyrrolidin-1-yl)pyridine-3,5-dicarbonitrile
synonym: neladenoson dalanate (deprecated INN)
synonym: BAY 1067197
synonym: BAY-1067197
synonym: BAY1067197 (amide ester prodrug)
approved: f
ligand name: neladenoson
type: SyntheticOrganicLigand

capadenoson
canonical SMILES: OCCOc1ccc(cc1)c1c(C#N)c(SCc2csc(n2)c2ccc(cc2)Cl)nc(c1C#N)N
isomeric SMILES: OCCOc1ccc(cc1)c1c(C#N)c(SCc2csc(n2)c2ccc(cc2)Cl)nc(c1C#N)N
in ch i key: CITWCLNVRIKQAF-UHFFFAOYSA-N
comment: Capadenoson is an investigational, selective partial agonist of adenosine A1 receptor <Reference id=40332/>. Its pharmacokinetics support oral once daily administration.
iupac name: 2-amino-6-[[2-(4-chlorophenyl)-1,3-thiazol-4-yl]methylsulfanyl]-4-[4-(2-hydroxyethoxy)phenyl]pyridine-3,5-dicarbonitrile
xref: CHEMBL3235279
synonym: BAY 68-4986
synonym: BAY-68-4986
synonym: BAY684986
approved: f
ligand name: capadenoson
type: SyntheticOrganicLigand

suprastat
in ch i key: VTRGFHYHEAEHGS-UHFFFAOYSA-N
in ch i: InChI=1S/C20H26N4O4/c21-13-15-5-9-18(10-6-15)22-20(27)24(11-1-2-12-25)14-16-3-7-17(8-4-16)19(26)23-28/h3-10,25,28H,1-2,11-14,21H2,(H,22,27)(H,23,26)
comment: Suprastat is a selective histone deacetylase (HDAC) 6 inhibitor <Reference id=40316/>. It is reported to potentiate anti-PD1 immunotherapy in an in vivo melanoma model.
iupac name: 4-((3-(4-(Aminomethyl)phenyl)-1-(4-hydroxybutyl)ureido)methyl)-N-hydroxy-benzamide
synonym: compound 6a [PMID: 32815366]
approved: f
ligand name: suprastat
type: SyntheticOrganicLigand

DSM502
in ch i key: AFOVOYRODSYDMK-UHFFFAOYSA-N
in ch i: InChI=1S/C16H16F3N3O/c1-9-11(8-21-14(9)15(23)22-12-3-4-12)6-10-2-5-13(20-7-10)16(17,18)19/h2,5,7-8,12,21H,3-4,6H2,1H3,(H,22,23)
comment: DSM502 is the optimized lead from a pyrrole-based series of antimalarial compounds that inhibit P. falciparum dihydroorotate dehydrogenase (PfDHODH) <Reference id=40466/>. This series of PfDHODH inhibitors could provide a potential backup candidate, with an alternative scaffold, to the clinical lead <Ligand id=9644/>. The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
iupac name: N-cyclopropyl-3-methyl-4-[[6-(trifluoromethyl)pyridin-3-yl]methyl]-1H-pyrrole-2-carboxamide
xref: CHEMBL4633246
approved: f
ligand name: DSM502
type: SyntheticOrganicLigand

bromhexine
canonical SMILES: Brc1cc(CN(C2CCCCC2)C)c(c(c1)Br)N
isomeric SMILES: Brc1cc(CN(C2CCCCC2)C)c(c(c1)Br)N
in ch i key: OJGDCBLYJGHCIH-UHFFFAOYSA-N
in ch i: InChI=1S/C14H20Br2N2/c1-18(12-5-3-2-4-6-12)9-10-7-11(15)8-13(16)14(10)17/h7-8,12H,2-6,9,17H2,1H3
comment: Bromhexine is a widely used mucolytic (expectorant) drug. In response to the SARS-CoV-2 pandemic of 2019/20 it was investigated as an add-on treatment for patients with COVID-19 <Reference id=40313/>. In addition to its mucolytic activity, bromhexine may also inhibit the human protease TMPRSS2 that is exploited by certain coronaviruses for spike (S) protein priming, thus reducing the viruses' infection mechanism <Reference id=40312/>.
xref: CHEMBL253376
synonym: NA-274
synonym: NA274
synonym: Bisolvon®
approved: t
ligand name: bromhexine
type: SyntheticOrganicLigand

compound 6j [PMID: 32747425]
in ch i key: COXVPYKZDDKVRF-ULQDDVLXSA-N
in ch i: InChI=1S/C21H33F2N3O5/c1-13(2)9-17(19(29)25-16(11-27)10-15-5-8-24-18(15)28)26-20(30)31-12-14-3-6-21(22,23)7-4-14/h11,13-17H,3-10,12H2,1-2H3,(H,24,28)(H,25,29)(H,26,30)/t15-,16-,17-/m0/s1
comment: Compound 6j is reported as an inhibitor of the 3CL proteinases (3CLpro) from MERS, SARS-CoV and SARS-CoV-2 coronaviruses <Reference id=40311/>.
iupac name: (4,4-difluorocyclohexyl)methyl N-[(1S)-3-methyl-1-{[(2S)-1-oxo-3-[(3S)-2-oxopyrrolidin-3-yl]propan-2-yl]carbamoyl}butyl]carbamate
approved: f
ligand name: compound 6j [PMID: 32747425]
type: SyntheticOrganicLigand

obatoclax
canonical SMILES: COc1c/c(=C/2/C=c3c(=N2)cccc3)/[nH]/c/1=C/c1[nH]c(cc1C)C
isomeric SMILES: COc1c/c(=C/2/C=c3c(=N2)cccc3)/[nH]/c/1=C/c1[nH]c(cc1C)C
in ch i key: CVCLJVVBHYOXDC-LKIBBAOUSA-N
in ch i: InChI=1S/C20H19N3O/c1-12-8-13(2)21-16(12)10-19-20(24-3)11-18(23-19)17-9-14-6-4-5-7-15(14)22-17/h4-11,21,23H,1-3H3/b18-17+,19-10-
comment: Obatoclax is a small molecule inhibitor of Bcl-2 family proteins. Bcl-2 inhibition induces apoptosis in cancer cells <Reference id=39796/><Reference id=39795/><Reference id=39797/>. We have matched the chemical structure to PubChem using the CAS number assigned in the WHO INN record for this drug, but note that various cis/trans isomers have been submitted to PubChem, and also thta the INN record does not in fact stipulate bond rotations. Enclosure of obatoclax in red blood-cell membrane-derived nanoparticles has been tested to overcome the compound's poor solubility <Reference id=39798/>.
synonym: SB16622
synonym: GX15-070
synonym: obatoclax mesylate
synonym: GX-15-070
approved: f
ligand name: obatoclax
type: SyntheticOrganicLigand

DIM
canonical SMILES: c1ccc2c(c1)c(c[nH]2)Cc1c[nH]c2c1cccc2
isomeric SMILES: c1ccc2c(c1)c(c[nH]2)Cc1c[nH]c2c1cccc2
in ch i key: VFTRKSBEFQDZKX-UHFFFAOYSA-N
in ch i: InChI=1S/C17H14N2/c1-3-7-16-14(5-1)12(10-18-16)9-13-11-19-17-8-4-2-6-15(13)17/h1-8,10-11,18-19H,9H2
comment: Positive allosteric modulator of GPR84.
iupac name: 3-(1H-indol-3-ylmethyl)-1H-indole
approved: f
ligand name: DIM
type: SyntheticOrganicLigand

DPO-1
in ch i key: BPCNGVCAHAIZEE-COPCDDAFSA-N
in ch i: InChI=1S/C22H29OP/c1-17(2)21-15-14-18(3)16-22(21)24(23,19-10-6-4-7-11-19)20-12-8-5-9-13-20/h4-13,17-18,21-22H,14-16H2,1-3H3/t18-,21+,22+/m1/s1
comment: DPO-1 is a Kv1.5 channel blocker <Reference id=40296/>.
iupac name: [[(1S,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl]-phenylphosphoryl]benzene
xref: CHEMBL1088844
synonym: diphenyl phosphine oxide-1
synonym: DPO1
approved: f
ligand name: DPO-1
type: SyntheticOrganicLigand

AVE1231
in ch i key: BFQMQSIBOHOPCY-QGZVFWFLSA-N
in ch i: InChI=1S/C20H27N3O4S/c1-4-6-13-28(25,26)23-18-10-8-7-9-16(18)20(24)22-17(5-2)15-11-12-19(27-3)21-14-15/h7-12,14,17,23H,4-6,13H2,1-3H3,(H,22,24)/t17-/m1/s1
comment: AVE1231 is a K2P3.1 (TASK-1) channel blocker <Reference id=40293/><Reference id=40416/>. It was originally reported as a inhibitor of hKv1.5 currents <Reference id=40294/><Reference id=40295/>, and was being developed as an atrial-selective drug therapy by Sanofi-Aventis for the treatment of atrial fibrillation, but the programme was terminated at Phase 1.
iupac name: 2-(butylsulfonylamino)-N-[(1R)-1-(6-methoxypyridin-3-yl)propyl]benzamide
synonym: A293
synonym: A-293
synonym: AVE-1231
approved: f
ligand name: AVE1231
type: SyntheticOrganicLigand

LYS006
in ch i key: ZEGMEJVULDALSH-NSHDSACASA-N
comment: LYS006 is one of the chemical structures claimed in a Novartis patent as inhibitors of leukotriene A4 hydrolase (LTA4H) <Reference id=40291/>. Both the (R) and (S) stereoisomers are claimed (examples 3 and 29 respectively). Both isomers have similar inhibitory potency in vitro. The (3S)-enantiomer was disclosed as LYS006 in 2021 <Reference id=42106/>, and at that point we modified our record to reflect this updated information. LYS006 is being developed for immunomodulatory action that can be applied to acute and chronic inflammation and autoinflammatory disorders.
iupac name: (3S)-3-amino-4-[5-[4-(5-chloro-3-fluoropyridin-2-yl)oxyphenyl]tetrazol-2-yl]butanoic acid
synonym: LYS-006
approved: f
ligand name: LYS006
type: SyntheticOrganicLigand

AZD8154
in ch i key: XOMFDZJQLSPGGV-INIZCTEOSA-N
in ch i: InChI=1S/C27H29N5O4S2/c1-15-25(37-27(28-15)30-21-6-4-7-22(29-21)31-11-5-8-23(31)33)18-12-19-14-32(16(2)17-9-10-17)26(34)24(19)20(13-18)38(3,35)36/h4,6-7,12-13,16-17H,5,8-11,14H2,1-3H3,(H,28,29,30)/t16-/m0/s1
comment: AZD8154 is one of the chemical structures in a patent from AstraZeneca that claims dual phosphatidylinositol 3-kinase (PI3K) δ/γ inhibitors <Reference id=40290/>. Its discovery was formally disclosed by Perry et al., in June 2021 <Reference id=42514/>.
iupac name: 2-[(1S)-1-cyclopropylethyl]-5-[4-methyl-2-[[6-(2-oxopyrrolidin-1-yl)pyridin-2-yl]amino]-1,3-thiazol-5-yl]-7-methylsulfonyl-3H-isoindol-1-one
synonym: AZD-8154
synonym: Example 1 [WO2018055040A1]
approved: f
ligand name: AZD8154
type: SyntheticOrganicLigand

compound 71 [WO2018191577A1]
in ch i key: JSAQBOQCZJHWMA-UHFFFAOYSA-N
in ch i: InChI=1S/C28H34N10O2/c1-28(2,3)38-15-25(34-35-38)26(39)32-24-8-10-37(21-16-40-17-21)13-19-11-18(5-6-22(19)24)23-7-9-29-27(33-23)31-20-12-30-36(4)14-20/h5-7,9,11-12,14-15,21,24H,8,10,13,16-17H2,1-4H3,(H,32,39)(H,29,31,33)
comment: Compound 71 is claimed in a Biogen patent as a Bruton's tyrosine kinase (BTK) inhibitor <Reference id=40289/>. This chemical structure, but with one specified stereo bond was disclosed as Biogen's clinical lead <Ligand id=11791/> in 2021 <Reference id=43167/>.
iupac name: 1-tert-butyl-N-[8-[2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]-2-(oxetan-3-yl)-1,3,4,5-tetrahydro-2-benzazepin-5-yl]triazole-4-carboxamide
synonym: compound 71 [WO2018191577A1]
approved: f
ligand name: compound 71 [WO2018191577A1]
type: SyntheticOrganicLigand

GB1211
in ch i key: FNCLKJPMEFPXOR-UHFFFAOYSA-N
comment: GB1211 is an orally active small molecule <Ligand id=6619/> inhibitor <Reference id=40285/><Reference id=44158/>. It was developed by Galecto Biotech for the treatment of fibrotic disease and cancer. In the fibrotic setting, blocking galectin-3's biological function is predicted to combat the enhanced TGF-β receptor-mediated macrophage differentiation and myofibroblast activation that drives pathological fibrotic changes <Reference id=40286/><Reference id=40287/><Reference id=40288/>.
iupac name: 2-(5-bromopyridin-3-yl)sulfanyl-6-(hydroxymethyl)-4-[4-(3,4,5-trifluorophenyl)triazol-1-yl]oxane-3,5-diol
synonym: GB-1211
synonym: Example 44 [WO2016120403A1]
synonym: compound 11d [Zetterberg et al., 2022]
approved: f
ligand name: GB1211
type: SyntheticOrganicLigand

MMV030084
in ch i key: YRHGMGAVJILIGS-UHFFFAOYSA-N
in ch i: InChI=1S/C18H19ClN4O/c1-18(2,10-20)17-22-15(11-5-7-21-8-6-11)16(23-17)12-3-4-13(19)14(24)9-12/h3-9,24H,10,20H2,1-2H3,(H,22,23)
comment: MMV030084 is a trisubstituted imidazole, with potent antimalarial activity against multiple stages of the Plasmodium lifecycle <Reference id=40278/>. The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
iupac name: 5-[2-(1-amino-2-methylpropan-2-yl)-5-pyridin-4-yl-1H-imidazol-4-yl]-2-chlorophenol
xref: CHEMBL200889
synonym: TCMDC-140369
approved: f
ligand name: MMV030084
type: SyntheticOrganicLigand

rineterkib
in ch i key: YFCIFWOJYYFDQP-PTWZRHHISA-N
comment: The chemical structure that was submitted to the WHO for INN rineterkib (LTT462), is claimed as example 184 in Novartis' kinase inhibitor patent WO2015066188A1 <Reference id=40280/>. This structure maps to PubChem CID: 118045847 which provides an indication that it is an ERK inhibitor.
xref: CHEMBL3909517
synonym: ERK-IN-1
synonym: example 184 [WO2015066188A1]
synonym: LTT-462
synonym: LTT462
approved: f
ligand name: rineterkib
type: SyntheticOrganicLigand

tenofovir
canonical SMILES: C[C@H](Cn1cnc2c1ncnc2N)OCP(=O)(O)O
isomeric SMILES: C[C@H](Cn1cnc2c1ncnc2N)OCP(=O)(O)O
in ch i key: SGOIRFVFHAKUTI-ZCFIWIBFSA-N
in ch i: InChI=1S/C9H14N5O4P/c1-6(18-5-19(15,16)17)2-14-4-13-7-8(10)11-3-12-9(7)14/h3-4,6H,2,5H2,1H3,(H2,10,11,12)(H2,15,16,17)/t6-/m1/s1
comment: Tenofovir is a nucleotide reverse transcriptase inhibitor (NtRTI) antiretroviral compound. The R-enantiomer, as shown here, is more effective at inhibiting retroviruses than the S-enantiomer <Reference id=39519/>. Tenofovir has poor oral bioavailability and is delivered as either the prodrug tenofovir disoproxil fumarate (Viread®) or tenofovir alafenamide fumerate (Vemlidy®).
iupac name: [(2R)-1-(6-aminopurin-9-yl)propan-2-yl]oxymethylphosphonic acid
xref: CHEMBL483
synonym: PMPA
synonym: (R)-PMPA
synonym: tenofovir (anhydrous)
approved: t
ligand name: tenofovir
type: SyntheticOrganicLigand

senaparib
in ch i key: VBTUJTGLLREMNW-UHFFFAOYSA-N
in ch i: InChI=1S/C24H20F2N6O3/c25-17-6-5-15(14-32-19-4-1-3-18(26)20(19)21(33)29-24(32)35)13-16(17)22(34)30-9-11-31(12-10-30)23-27-7-2-8-28-23/h1-8,13H,9-12,14H2,(H,29,33,35)
comment: Senaparib (IMP4297) is an oral PARP1 inhibitor that is being developed in a joint venture between IMPACT Therapeutics and Junshi Biosciences, for the treatment of BRCA-mutated solid tumours. It is one of the chemical structures claimed in patent WO2012130166A1 <Reference id=40276/>.
iupac name: 5-fluoro-1-[[4-fluoro-3-(4-pyrimidin-2-ylpiperazine-1-carbonyl)phenyl]methyl]quinazoline-2,4-dione
synonym: IMP-4297
synonym: IMP4297
approved: f
ligand name: senaparib
type: SyntheticOrganicLigand

taletrectinib
in ch i key: HEVHTYMYEMEBPX-UHFFFAOYSA-N
in ch i: InChI=1S/C23H24FN5O/c1-15(25)14-30-20-8-6-17(7-9-20)21-13-26-23-11-10-22(28-29(21)23)27-16(2)18-4-3-5-19(24)12-18/h3-13,15-16H,14,25H2,1-2H3,(H,27,28)
comment: Taletrectinib (DS-6051b) is a next-generation selective ROS1/NTRK inhibitor <Reference id=40274/>. It was designed to treat ROS1- or NTRK-rearranged cancers. DS-6051b is able to inhibit the ROS1G2032R mutation that confers resistance to <Ligand id=4903/>, <Ligand id=7476/> and <Ligand id=8290/>. The compound originates from Daiichi Sankyo and has been licensed to AnHeart.
iupac name: 3-[4-[(2R)-2-aminopropoxy]phenyl]-N-[(1R)-1-(3-fluorophenyl)ethyl]imidazo[1,2-b]pyridazin-6-amine
synonym: AB-106
synonym: AB106
synonym: DS6051b
synonym: DS-6051b
approved: f
ligand name: taletrectinib
type: SyntheticOrganicLigand

compound 2 [PMID: 31932225]
in ch i key: NNVMPPRFBOTMMO-UHFFFAOYSA-N
comment: This compound is an agonist of hydroxycarboxylic acid receptor 1 (HCAR1, formerly GPR81) <Reference id=40270/><Reference id=40271/>.
iupac name: 1-[2-chloro-4-ethoxy-5-(morpholin-4-yl)benzoyl]-3-{6-[(4-methylpiperazin-1-yl)methyl]-1,3-benzothiazol-2-yl}urea
synonym: AZ2
approved: f
ligand name: compound 2 [PMID: 31932225]
type: SyntheticOrganicLigand

ICOA-13
in ch i key: UCZXUWQDKMFXCJ-UHFFFAOYSA-N
in ch i: InChI=1S/C45H56N6O9S2/c1-8-50-36-18-16-32(61(54,55)56)27-34(36)44(3,4)39(50)13-12-14-40-45(5,6)35-28-33(62(57,58)59)17-19-37(35)51(40)25-11-9-10-15-41(53)47-24-26-49-29-31(22-23-46-30(2)52)43-38(49)20-21-42(48-43)60-7/h12-14,16-21,27-29H,8-11,15,22-26H2,1-7H3,(H3-,46,47,52,53,54,55,56,57,58,59)
comment: ICOA-13 is a fluorescent Cy3 labeled non-selective melatonin receptor ligand <Reference id=40268/>. It is the first cell-impermeant melatonin receptor ligand.
iupac name: E-1-(6-(2-(3-(2-acetamidoethyl)-5-methoxy-1H-pyrrolo[3,2-b]pyridin-1-yl)ethylamino)-6-oxohexyl)-2-((E)-3-(1-ethyl-3,3-dimethyl-5-sulfo-3H-indolium-2-yl)allylidene)-3,3-dimethylindoline-5-sulfonate
approved: f
ligand name: ICOA-13
type: SyntheticOrganicLigand

TUG-1197
in ch i key: LDMHZAQFLWCKDT-UHFFFAOYSA-N
in ch i: InChI=1S/C18H13FN2O3S/c19-14-9-15(11-16(10-14)24-18-7-3-4-8-20-18)21-12-13-5-1-2-6-17(13)25(21,22)23/h1-11H,12H2
comment: TUG-1197 is a selective agonist of free fatty acid receptor 4 (FFAR4) <Reference id=40233/><Reference id=40232/>.
iupac name: 2-(3-fluoro-5-pyridin-2-yloxyphenyl)-3H-1,2-benzothiazole 1,1-dioxide
xref: CHEMBL3941880
synonym: compound 34 [PMID: 27570890]
synonym: TUG1197
approved: f
ligand name: TUG-1197
type: SyntheticOrganicLigand

odevixibat
in ch i key: XULSCZPZVQIMFM-IPZQJPLYSA-N
in ch i: InChI=1S/C37H48N4O8S2/c1-5-8-19-37(20-9-6-2)24-41(26-13-11-10-12-14-26)29-21-31(50-4)30(22-32(29)51(47,48)40-37)49-23-33(43)39-34(25-15-17-27(42)18-16-25)35(44)38-28(7-3)36(45)46/h10-18,21-22,28,34,40,42H,5-9,19-20,23-24H2,1-4H3,(H,38,44)(H,39,43)(H,45,46)/t28-,34+/m0/s1
comment: Odevixibat is an inhibitor of ileal bile acid transporter (IBAT, or apical sodium-dependent bile acid transporter ASBT; SLC10A2). It was developed by Albireo for potential to treat rare pediatric cholestatic liver diseases, including progressive familial intrahepatic cholestasis (PFIC) and biliary atresia. In July 2021 it became the first drug to be approved as a treament for PFIC-associated pruritus.
iupac name: (2S)-2-[[(2R)-2-[[2-[(3,3-dibutyl-7-methylsulfanyl-1,1-dioxo-5-phenyl-2,4-dihydro-1λ6,2,5-benzothiadiazepin-8-yl)oxy]acetyl]amino]-2-(4-hydroxyphenyl)acetyl]amino]butanoic acid
xref: CHEMBL4297588
synonym: A4250
synonym: A-4250
synonym: Unk-D-nTyr-Abu-OH (IUPAC condensed name)
synonym: example 5 [US9694018B1]
synonym: Bylvay®
approved: t
ligand name: odevixibat
type: SyntheticOrganicLigand

ZYBT1
in ch i key: YMCOZPHXLROTBV-UHFFFAOYSA-N
in ch i: InChI=1S/C27H26N8O2/c1-2-22(36)34-13-18-11-20(12-19(18)14-34)35-26-23(25(28)30-15-31-26)24(33-35)16-6-8-17(9-7-16)27(37)32-21-5-3-4-10-29-21/h2-10,15,18-20H,1,11-14H2,(H2,28,30,31)(H,29,32,37)
comment: ZYBT1 is reported as a potent and irreversible Bruton's tyrosine kinase (BTK) inhibitor <Reference id=40225/><Reference id=40224/>. It is able to inhibit the <Ligand id=6912/>-resistant BTKC481S mutant. ZYBT1 mediates anti-inflammatory activity in models of rheumatoid arthritis and has antiproliferative action against B-cell lymphoma xenograft tumours <Reference id=40225/>.
iupac name: 4-[4-amino-1-(2-prop-2-enoyl-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrol-5-yl)pyrazolo[3,4-d]pyrimidin-3-yl]-N-pyridin-2-ylbenzamide
synonym: example 13 [WO2015132799A2]
approved: f
ligand name: ZYBT1
type: SyntheticOrganicLigand

IACS-9439
in ch i key: JYFJGEOXSQLPMB-HOTGVXAUSA-N
comment: IACS-9439 is a potent, highly selective, and orally bioavailable CSF1R inhibitor <Reference id=40223/>. It was developed to reduce the number of immune-suppressive tumour-associated macrophages in the tumour microenvironment, as an approach to promote tumour growth inhibition.
iupac name: (1S,2S)-2-[[7-chloro-4-methoxy-6-[[2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]methoxy]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol
synonym: compound 1 [PMID: 32787110]
approved: f
ligand name: IACS-9439
type: SyntheticOrganicLigand

vodobatinib
in ch i key: ZQOBVMHBVWNVBG-UHFFFAOYSA-N
in ch i: InChI=1S/C27H20ClN3O2/c1-17-10-12-22(26(32)30-31-27(33)25-18(2)6-5-8-23(25)28)15-20(17)13-11-19-14-21-7-3-4-9-24(21)29-16-19/h3-10,12,14-16H,1-2H3,(H,30,32)(H,31,33)
comment: The chemical structure submitted to the WHO for the INN vodobatinib is identical to that of Sun Pharma's Bcr-Abl1 inhibitor SCO-088 (SUN-K706, or simply K0706), via a PubChem structure match. SCO-088 is a third generation Bcr-Abl1 tyrosine kinase inhibitor that was developed to combat treatment resistant chronic myeloid leukemia (CML) <Reference id=40217/>.
iupac name: 2-chloro-6-methyl-N'-[4-methyl-3-(2-quinolin-3-ylethynyl)benzoyl]benzohydrazide
xref: CHEMBL4130229
synonym: SUN-K706
synonym: SUNK706
synonym: SCO088
synonym: SCO-088
approved: f
ligand name: vodobatinib
type: SyntheticOrganicLigand

dalpiciclib
in ch i key: SGJLSPUSUBJWHO-UHFFFAOYSA-N
in ch i: InChI=1S/C25H30N6O2/c1-15-20-14-28-25(29-21-8-7-18(13-27-21)17-9-11-26-12-10-17)30-23(20)31(19-5-3-4-6-19)24(33)22(15)16(2)32/h7-8,13-14,17,19,26H,3-6,9-12H2,1-2H3,(H,27,28,29,30)
comment: The chemical structure submitted to the WHO for the INN dalpiciclib is identical to that of the orally administered CDK4/6 inhibitor SHR6390, via a PubChem structure match. Pharmacological and preclinical anti-tumour data for SHR6390 have been published <Reference id=40213/><Reference id=40214/>, albeit without name>structure disclosure. SHR6390 was designed by Jiangsu Hengrui Medicine Company.
iupac name: 6-acetyl-8-cyclopentyl-5-methyl-2-[(5-piperidin-4-ylpyridin-2-yl)amino]pyrido[2,3-d]pyrimidin-7-one
synonym: SHR-6390
synonym: Example 1 [WO2014183520A1]
synonym: SHR6390
approved: f
ligand name: dalpiciclib
type: SyntheticOrganicLigand

dalosirvat
canonical SMILES: O=C(c1ccc2c(c1)OCCO2)CCC(=O)c1ccccc1
isomeric SMILES: O=C(c1ccc2c(c1)OCCO2)CCC(=O)c1ccccc1
in ch i key: AOCDRSSVFUCURK-UHFFFAOYSA-N
in ch i: InChI=1S/C18H16O4/c19-15(13-4-2-1-3-5-13)7-8-16(20)14-6-9-17-18(12-14)22-11-10-21-17/h1-6,9,12H,7-8,10-11H2
comment: The chemical structure that was submitted to the WHO for the INN dalosirvat (in which it is defined as a 'sirtuin activator'), is a match with compound 1 as claimed in Wintherix's patent as a Wnt pathway activator <Reference id=40212/>. Speculatively dalosirvat may be Samumed's SM04554, which is a clinical lead being investigated as a topical therapy to promote hair follicle development and hair regrowth in individuals suffering from androgenetic alopecia (Phase 2/3 NCT03742518). As of August 2020, there has been no formal name>structure disclosure for SM04554.
iupac name: 1-(2,3-dihydro-1,4-benzodioxin-6-yl)-4-phenylbutane-1,4-dione
synonym: compound 1 [WO2012024404A1]
approved: f
ligand name: dalosirvat
type: SyntheticOrganicLigand

ipivivint
in ch i key: YBBUGSYNPXTSGW-UHFFFAOYSA-N
in ch i: InChI=1S/C26H21FN8/c1-35(2)14-15-6-17(10-28-9-15)18-8-20-24(33-34-25(20)30-11-18)26-31-22-13-29-12-21(23(22)32-26)16-4-3-5-19(27)7-16/h3-13H,14H2,1-2H3,(H,31,32)(H,30,33,34)
comment: The chemical structure that was submitted to the WHO for the INN ipivivint leads to Samumed's patent WO2013166396A2 , as compound 18 therein <Reference id=40209/>. Ipivivint is defined as a Wnt pathway inhibitor. Samumed have a lead candidate called SM08502 in their pipeline. SM08502 is reported to decrease Wnt signalling in tumour cells via inhibition of CDC-like kinase (CLK) activity in an article from Samumed scientists <Reference id=40210/>. We speculate that ipivivint might be SM08502, but as of August 2020 there is no formal disclosure of SM08502's chemical structure. SM08502 is being investigated in a Phase 1 clinical trial in patients with advanced solid tumours (NCT03355066).
synonym: example 18 [WO2013166396A2]
approved: f
ligand name: ipivivint
type: SyntheticOrganicLigand

(R)-ND-336
in ch i key: GRRDUDJQILRRES-OAHLLOKOSA-N
in ch i: InChI=1S/C16H17NO3S2/c17-9-12-1-3-13(4-2-12)20-14-5-7-16(8-6-14)22(18,19)11-15-10-21-15/h1-8,15H,9-11,17H2/t15-/m1/s1
comment: (R)-ND-336 is an inhibitor of matrix metalloproteases (MMP) -9, -2 and -14 <Reference id=39419/>. MMP-9 has been identified as a potential therapeutic target for the treatment of diabetic foot ulcers, where upregulation of active MMP-9 is detrimental to healing. (R)-ND-336 is selective for MMP-9 compared to MMP-8 in this target tissue, and the (S) enantiomer is less active in in vivo wound healing than the (R) enantiomer.
xref: CHEMBL4300809
approved: f
ligand name: (R)-ND-336
type: SyntheticOrganicLigand

darovasertib
in ch i key: XXJXHXJWQSCNPX-UHFFFAOYSA-N
in ch i: InChI=1S/C22H23F3N8O/c1-21(27)6-10-33(11-7-21)15-5-3-9-29-19(15)32-20(34)17-18(26)30-12-14(31-17)16-13(22(23,24)25)4-2-8-28-16/h2-5,8-9,12H,6-7,10-11,27H2,1H3,(H2,26,30)(H,29,32,34)
comment: Darovasertib (LXS196) is an oral protein kinase C (PKC) inhibitor that was developed by Novartis for antineoplastic potential. It is one of the chemical structures claimed in Novartis' patent WO2016020864A1 <Reference id=40205/>. Darovasertib is a potential first-in-class protein kinase C (PKC) inhibitor.
iupac name: 3-amino-N-[3-(4-amino-4-methylpiperidin-1-yl)pyridin-2-yl]-6-[3-(trifluoromethyl)pyridin-2-yl]pyrazine-2-carboxamide
xref: CHEMBL3982723
synonym: LXS-196
synonym: NVP-LXS196
synonym: Example 9 [WO2016020864A1]
synonym: LXS196
synonym: IDE196
synonym: IDE-196
approved: f
ligand name: darovasertib
type: SyntheticOrganicLigand

ilacirnon
in ch i key: LUUMLYXKTPBTQR-UHFFFAOYSA-N
comment: Ilacirnon (CCX140B) is a clinical stage, orally administered antagonist of the chemokine receptor CCR2 <Reference id=33684/>. It was developed by Chemocentryx. The chemical structure of CCX140B matches that submitted to the WHO for the INN ilacirnon, and is one of those claimed in Chemocentryx's patent WO2009009740A1 <Reference id=40203/>
iupac name: 4-chloro-N-[5-methyl-2-(7H-pyrrolo[2,3-d]pyrimidine-4-carbonyl)pyridin-3-yl]-3-(trifluoromethyl)benzenesulfonamide
xref: CHEMBL2178573
synonym: Example 5 [WO2009009740A1]
synonym: CCX140-B
synonym: CCX-140B
synonym: CCX140
synonym: CCX140B
approved: f
ligand name: ilacirnon
type: SyntheticOrganicLigand

venadaparib
in ch i key: YNBQAYKYNYRCCA-UHFFFAOYSA-N
in ch i: InChI=1S/C23H23FN4O2/c24-20-8-5-14(10-21-17-3-1-2-4-18(17)22(29)27-26-21)9-19(20)23(30)28-12-15(13-28)11-25-16-6-7-16/h1-5,8-9,15-16,25H,6-7,10-13H2,(H,27,29)
comment: This compound is one of the phthalazinone derivatives claimed as poly(ADP-ribose) polymerase (PARP) inhibitors in Ildong Pharmaceutical's patent WO2015037939A1, that were designed for antineoplastic potential <Reference id=40201/>. The chemical structure matches that submitted to the WHO for the INN venadaparib. We have added its interaction data to PARP1. A potential Ildong internal code is IDX-1197, which is described by the NCI Drug Dictionary as an orally administered, PARP1/2 selective inhibitor, and this entry associates IDX-1197 with an earlier synonym, NOV140101. As of August 2020, there is nothing in the published literature to confirm these structure>code associations. Pharmacological and biological activity of IDX-1197 is outlined in Abstract A106; AACR-NCI-EORTC International Conference (Oct 2017). IDX-1197 is in Phase 1/2 clinical trial in solid tumours with confirmed mutations in homologous recombination repair genes (NCT04174716).
iupac name: 4-[[3-[3-[(cyclopropylamino)methyl]azetidine-1-carbonyl]-4-fluorophenyl]methyl]-2H-phthalazin-1-one
synonym: example I-26 [WO2015037939A1]
synonym: example 26 [WO2015037939A1]
approved: f
ligand name: venadaparib
type: SyntheticOrganicLigand

vamifeport
in ch i key: KNYVRFXIVWUGBZ-UHFFFAOYSA-N
in ch i: InChI=1S/C21H21FN6O2/c22-14-4-3-9-24-17(14)12-25-21(29)18-13-30-20(28-18)8-11-23-10-7-19-26-15-5-1-2-6-16(15)27-19/h1-6,9,13,23H,7-8,10-12H2,(H,25,29)(H,26,27)
comment: Vamifeport (VIT-2763) is a first in-class, orally administered small molecule inhibitor of ferroportin (SLC40A1) <Reference id=40200/>. It was developed by Vifor Pharma for the prevention of iron overload and to treat β-thalassaemia.
iupac name: 2-[2-[2-(1H-benzimidazol-2-yl)ethylamino]ethyl]-N-[(3-fluoropyridin-2-yl)methyl]-1,3-oxazole-4-carboxamide
synonym: VIT2763
synonym: VIT-2763
approved: f
ligand name: vamifeport
type: SyntheticOrganicLigand

IcatCXPZ-01
in ch i key: LJIOTBMDLVHTBO-CUYJMHBOSA-N
in ch i: InChI=1S/C25H31N5O3S/c1-3-23(27)24(31)28-25(17-26)16-22(25)20-6-4-18(5-7-20)19-8-10-21(11-9-19)34(32,33)30-14-12-29(2)13-15-30/h4-11,22-23H,3,12-16,27H2,1-2H3,(H,28,31)/t22-,23+,25+/m1/s1
comment: IcatCXPZ-01 is a cathepsin C inhibitor <Reference id=40176/>.
synonym: XPZ-01
synonym: compound 8a [PMID: 30978322]
approved: f
ligand name: IcatCXPZ-01
type: SyntheticOrganicLigand

Crotamiton
canonical SMILES: C/C=C/C(=O)N(c1ccccc1C)CC
isomeric SMILES: C/C=C/C(=O)N(c1ccccc1C)CC
in ch i key: DNTGGZPQPQTDQF-XBXARRHUSA-N
in ch i: InChI=1S/C13H17NO/c1-4-8-13(15)14(5-2)12-10-7-6-9-11(12)3/h4,6-10H,5H2,1-3H3/b8-4+
comment: Crotamiton is a drug, available as a cream or lotion for topical use only, that is used both as a scabicidal (for treating scabies) and as a general antipruritic (anti-itching drug).
iupac name: (E)-N-ethyl-N-(2-methylphenyl)but-2-enamide
synonym: Eurax®
approved: t
ligand name: Crotamiton
type: SyntheticOrganicLigand

BIIB068
in ch i key: BMWMKGNVAMXXCH-UHFFFAOYSA-N
in ch i: InChI=1S/C23H29N7O2/c1-15(2)32-20-13-30(14-20)23(31)25-10-18-6-5-17(9-16(18)3)21-7-8-24-22(28-21)27-19-11-26-29(4)12-19/h5-9,11-12,15,20H,10,13-14H2,1-4H3,(H,25,31)(H,24,27,28)
comment: BIIB068 was designed as a novel, oral Bruton's tyrosine kinase (BTK) inhibitor and is intended for the treatment of autoimmune diseases <Reference id=40174/>. Pharmacokinetics of BIIB068 in humans have been determined in a Phase 1 study following a single, ascending oral dose.
iupac name: N-[[2-methyl-4-[2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]phenyl]methyl]-3-propan-2-yloxyazetidine-1-carboxamide
synonym: compound 1 [PMID: 32696648]
synonym: BIIB-068
approved: f
ligand name: BIIB068
type: SyntheticOrganicLigand

LW-213
in ch i key: CZZGXKYKSUTFEU-UHFFFAOYSA-N
in ch i: InChI=1S/C27H27NO5/c1-28(2)14-9-15-31-26-24(32-18-19-10-5-3-6-11-19)17-22(30)25-21(29)16-23(33-27(25)26)20-12-7-4-8-13-20/h3-8,10-13,16-17,30H,9,14-15,18H2,1-2H3
comment: LW-213 is a derivative of the plant flavinoid wogonin <Reference id=40173/>, and like its parent it has anticancer activity <Reference id=40170/><Reference id=40171/><Reference id=40172/>. Studies in human cutaneous T-cell lymphomas (CTCL) indicate that LW-213-induced apoptosis is mediated via activation of the PERK-eIF2α-ATF4-CHOP axis, and involves enhanced reactive oxygen species production and calcium-dependent endoplasmic reticulum stress. The primary molecular target of LW-213 has not been defined.
iupac name: 8-[3-(dimethylamino)propoxy]-5-hydroxy-2-phenyl-7-phenylmethoxychromen-4-one
xref: CHEMBL4207919
synonym: compound 18c [PMID: 28987604]
synonym: LW213
approved: f
ligand name: LW-213
type: SyntheticOrganicLigand

TG-0205221
in ch i key: YIWYOEOSWRXENJ-FFXRMZKPSA-N
in ch i: InChI=1S/C32H50N4O7/c1-21(43-32(2,3)4)27(36-31(41)42-20-23-13-9-6-10-14-23)30(40)35-26(17-22-11-7-5-8-12-22)29(39)34-25(19-37)18-24-15-16-33-28(24)38/h6,9-10,13-14,21-22,24-27,37H,5,7-8,11-12,15-20H2,1-4H3,(H,33,38)(H,34,39)(H,35,40)(H,36,41)/t21-,24+,25+,26+,27+/m1/s1
comment: TG-0205221 is an inhibitor of coronavirus main proteases, having originally been identified as a SARS-CoV Mpro inhibitor <Reference id=40146/>. TG-0205221 has been crystallised in complex with SARS-CoV and SARS-CoV-2 Mpro (RCSB Protein Data Bank accession 7C8T).
iupac name: benzyl N-[(2S,3R)-1-[[(2S)-3-cyclohexyl-1-[[(2S)-1-hydroxy-3-[(3S)-2-oxopyrrolidin-3-yl]propan-2-yl]amino]-1-oxopropan-2-yl]amino]-3-[(2-methylpropan-2-yl)oxy]-1-oxobutan-2-yl]carbamate
synonym: Cbz-Thr(tBu)-Cha-Ala(((S)-2-oxopyrrolidin-3-yl))-ol
synonym: TG0205221
synonym: N-benzyloxycarbonyl-O3-tert-butyl-L-threonyl-3-cyclohexyl-L-alanyl-3-((S)-2-oxopyrrolidin-3-yl)-L-alaninol
approved: f
ligand name: TG-0205221
type: PeptideLigand

MP13
in ch i key: RUHYGYHBVKWREW-CMOCDZPBSA-N
in ch i: InChI=1S/C26H38N4O6/c1-16(2)12-21(24(33)28-20(14-31)13-19-10-11-27-23(19)32)29-25(34)22(17(3)4)30-26(35)36-15-18-8-6-5-7-9-18/h5-9,14,16-17,19-22H,10-13,15H2,1-4H3,(H,27,32)(H,28,33)(H,29,34)(H,30,35)/t19-,20-,21-,22-/m0/s1
comment: MP13 is reported in a BioRxiv preprint as a nanomolar inhibitor of SARS-CoV-2 main protease (Mpro) <Reference id=40144/>. The same structure was claimed in a 2006 Pfizer patent %22Anticoronviral compounds and compositions, their pharmaceutical uses and materials for their synthesis%22 as example 13 <Reference id=40145/>.
synonym: example 13 [WO2006061714]
approved: f
ligand name: MP13
type: SyntheticOrganicLigand

DAV-CRI-14a23e73-1
in ch i key: QXFHJCBKHQAQDM-UHFFFAOYSA-N
comment: DAV-CRI-14a23e73-1 was identified as an inhibitor of SARS-CoV-2 main protease (Mpro) through PostEra's COVID moonshot open science screen.
iupac name: 2-chloro-N-(1-{5-chloro-4'-sulfamoyl-[1,1'-biphenyl]-3-yl}ethyl)acetamide
approved: f
ligand name: DAV-CRI-14a23e73-1
type: SyntheticOrganicLigand

GRL-0496
canonical SMILES: Clc1cncc(c1)OC(=O)c1cccc2c1cc[nH]2
isomeric SMILES: Clc1cncc(c1)OC(=O)c1cccc2c1cc[nH]2
in ch i key: BOSZJNSICHFHMA-UHFFFAOYSA-N
in ch i: InChI=1S/C14H9ClN2O2/c15-9-6-10(8-16-7-9)19-14(18)12-2-1-3-13-11(12)4-5-17-13/h1-8,17H
comment: This compound is an inhibitor of SARS coronavirus main proteases (a.k.a. 3CL protease). It was originally reported to inhibit Mpro from SARS-CoV <Reference id=40142/>, and was more recently identified through PostEra's COVID moonshot open science screen for inhibitors of SARS-CoV-2 Mpro.
iupac name: (5-chloropyridin-3-yl) 1H-indole-4-carboxylate
xref: CHEMBL490820
synonym: compound 10 [PMID:18796354]
synonym: ALP-POS-c59291d4-5
synonym: GRL0496
approved: f
ligand name: GRL-0496
type: SyntheticOrganicLigand

bedaquiline
in ch i key: QUIJNHUBAXPXFS-XLJNKUFUSA-N
in ch i: InChI=1S/C32H31BrN2O2/c1-35(2)19-18-32(36,28-15-9-13-22-10-7-8-14-26(22)28)30(23-11-5-4-6-12-23)27-21-24-20-25(33)16-17-29(24)34-31(27)37-3/h4-17,20-21,30,36H,18-19H2,1-3H3/t30-,32-/m1/s1
comment: Bedaquiline is a quinoline-based antimycobacterial drug that is used in the treatment of tuberculosis <Reference id=40136/>. Functionally, it inhibits mycobacterial ATP synthase and enhances the antibacterial activity of second-line drug combinations.
iupac name: (1R,2S)-1-(6-bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-2-naphthalen-1-yl-1-phenylbutan-2-ol
xref: CHEMBL376488
synonym: Sirturo®
synonym: TMC207
synonym: TMC-207
synonym: R-207910
synonym: compound 1a [PMID: 17496888]
synonym: BDQ
approved: t
ligand name: bedaquiline
type: SyntheticOrganicLigand

risdiplam
in ch i key: ASKZRYGFUPSJPN-UHFFFAOYSA-N
in ch i: InChI=1S/C22H23N7O/c1-14-9-18(26-29-11-15(2)24-21(14)29)17-10-20(30)28-12-16(3-4-19(28)25-17)27-8-7-23-22(13-27)5-6-22/h3-4,9-12,23H,5-8,13H2,1-2H3
comment: Risdiplam is a first-in-class, orally bioavailable splicing modifier <Reference id=40129/>. Like <Ligand id=9416/>, it is intended to improve the efficiency of SMN2 (HGNC ID 11118; Uniprot Q16637) gene transcription in patients with spinal muscular atrophy (SMA) <Reference id=40128/>.
xref: CHEMBL4297528
synonym: Evrysdi®
synonym: RG7916
synonym: RG-7916
synonym: RO7034067
synonym: RO-7034067
synonym: compound 1 [PMID: 30044619]
approved: t
ligand name: risdiplam
type: SyntheticOrganicLigand

pheniramine
canonical SMILES: CN(CCC(c1ccccn1)c1ccccc1)C
isomeric SMILES: CN(CCC(c1ccccn1)c1ccccc1)C
in ch i key: IJHNSHDBIRRJRN-UHFFFAOYSA-N
in ch i: InChI=1S/C16H20N2/c1-18(2)13-11-15(14-8-4-3-5-9-14)16-10-6-7-12-17-16/h3-10,12,15H,11,13H2,1-2H3
comment: Pheniramine is an antihistamine. Marketed formulations may contain pheniramine maleate (PubChem CID 5282139). Pheniramine is often contained in fixed-ratio formulations alongside other antihistamines and agents such as decongestants.
iupac name: dimethyl[3-phenyl-3-(pyridin-2-yl)propyl]amine
xref: CHEMBL1193
approved: t
ligand name: pheniramine
type: SyntheticOrganicLigand

carbetocin
in ch i key: NSTRIRCPWQHTIA-DTRKZRJBSA-N
comment: Carbetocin is an <Ligand id=2174/> analogue. Like oxytocin it acts as an oxytocic, antihemorrhagic and uterotonic drug. Activating this pathway has already been shown to reduce food intake and body weight in both animal models and human clinical studies, and as a result oxytocin (plus analogues and non-peptide mimetics) is being evaluated for anti-obesity potential <Reference id=40127/>.
iupac name: (2S)-N-[(2S)-1-[(2-amino-2-oxoethyl)amino]-4-methyl-1-oxopentan-2-yl]-1-[(3R,6S,9S,12S,15S)-6-(2-amino-2-oxoethyl)-9-(3-amino-3-oxopropyl)-12-[(2S)-butan-2-yl]-15-[(4-methoxyphenyl)methyl]-5,8,11,14,17-pentaoxo-1-thia-4,7,10,13,16-pentazacycloicosane-3-carbonyl]pyrrolidine-2-carboxamide
xref: CHEMBL3301668
synonym: Pabal®
approved: t
ligand name: carbetocin
type: PeptideLigand

ETC-1922159
in ch i key: QTRXIFVSTWXRJJ-UHFFFAOYSA-N
in ch i: InChI=1S/C19H17N7O3/c1-24-17-16(18(28)25(2)19(24)29)26(11-20-17)10-15(27)21-14-9-8-13(22-23-14)12-6-4-3-5-7-12/h3-9,11H,10H2,1-2H3,(H,21,23,27)
comment: ETC-1922159 (ETC-159) is an orally bioavailable, clinical stage porcupine inhibitor <Reference id=40114/><Reference id=40115/><Reference id=40117/>. It is being developed for oncology potential.
iupac name: 2-(1,3-dimethyl-2,6-dioxopurin-7-yl)-N-(6-phenylpyridazin-3-yl)acetamide
xref: CHEMBL3633802
synonym: ETC1922159
synonym: ETC-159
synonym: ETC159
approved: f
ligand name: ETC-1922159
type: SyntheticOrganicLigand

GSK2881078
in ch i key: SKDVMPZQJMZEAC-SECBINFHSA-N
comment: GSK2881078 is an orally bioavailable, small molecule, nonsteroidal selective androgen receptor modulator (SARM). It was developed by GSK to treat age-related muscle atrophy (loss of skeletal muscle mass, quality, and strength) <Reference id=40021/><Reference id=40022/>.
iupac name: 1-[(2R)-1-methylsulfonylpropan-2-yl]-4-(trifluoromethyl)indole-5-carbonitrile
synonym: GSK-2881078
synonym: GSK'078
approved: f
ligand name: GSK2881078
type: SyntheticOrganicLigand

LGK974
in ch i key: XXYGTCZJJLTAGH-UHFFFAOYSA-N
in ch i: InChI=1S/C23H20N6O/c1-15-9-17(12-28-23(15)18-5-6-25-16(2)10-18)11-22(30)29-21-4-3-19(13-27-21)20-14-24-7-8-26-20/h3-10,12-14H,11H2,1-2H3,(H,27,29,30)
comment: LGK974 is a clinical stage porcupine inhibitor <Reference id=40109/>. It is being developed as an oncology therapeutic <Reference id=40110/>. It is the first porcupine inhibitor to advance to clinical trial.
iupac name: 2-[5-methyl-6-(2-methylpyridin-4-yl)pyridin-3-yl]-N-(5-pyrazin-2-ylpyridin-2-yl)acetamide
xref: CHEMBL3188386
synonym: WNT-974
synonym: WNT974
synonym: LGK-974
approved: f
ligand name: LGK974
type: SyntheticOrganicLigand

GNF-6231
in ch i key: AXXNRMISICMFNS-UHFFFAOYSA-N
in ch i: InChI=1S/C24H25FN6O2/c1-16-11-18(14-28-24(16)19-5-6-26-21(25)13-19)12-23(33)29-22-4-3-20(15-27-22)31-9-7-30(8-10-31)17(2)32/h3-6,11,13-15H,7-10,12H2,1-2H3,(H,27,29,33)
comment: GNF-6231 is an experimental porcupine inhibitor <Reference id=40108/>. It has shown activity in rodent models of skin fibrosis <Reference id=40107/> and antitumour efficacy in a mouse MMTV-WNT1 xenograft tumour model.
synonym: compound 19 [PMID: 27437076]
synonym: GNF6231
approved: f
ligand name: GNF-6231
type: SyntheticOrganicLigand

S416
canonical SMILES: CN(c1scc(n1)c1ccccc1Cl)/N=C/c1ccccc1C(=O)O
isomeric SMILES: CN(c1scc(n1)c1ccccc1Cl)/N=C/c1ccccc1C(=O)O
in ch i key: MWIQPUXVXAVFRM-KEBDBYFISA-N
comment: S416 is an inhibitor of dihydroorotate dehydrogenase (DHODH) <Reference id=40096/>. It has been explored for antiviral activity against RNA viruses, including SARS-CoV-2, based on the rationale that viruses depend on host pyrimidine synthesis to maintain their replication, and that therefore inhibiting a crucial step in this synthetic pathway should limit viral replication. Mechanistically, S416 binds at the putative ubiquinone binding tunnel within the DHODH active site.
iupac name: 2-[(E)-{2-[4-(2-chlorophenyl)-1,3-thiazol-2-yl]-2-methylhydrazin-1-ylidene}methyl]benzoic acid
approved: f
ligand name: S416
type: SyntheticOrganicLigand

S312
canonical SMILES: Clc1ccccc1c1csc(n1)N/N=C/c1ccccc1C(=O)O
isomeric SMILES: Clc1ccccc1c1csc(n1)N/N=C/c1ccccc1C(=O)O
in ch i key: DDEIFUOYHWEWSS-DJKKODMXSA-N
comment: S312 is an inhibitor of dihydroorotate dehydrogenase (DHODH) <Reference id=40096/>. It was initially designed and reported for application as an anti-inflammatory agent <Reference id=40097/> and was effective in a mouse rheumatoid arthritis model. S312 has most recently been explored for antiviral activity against RNA viruses, including influenza virus strains, Zika and Ebola viruses and SARS-CoV-2, based on the rationale that viruses depend on host pyrimidine synthesis to maintain their replication rate, and that therefore inhibiting a crucial step in this synthetic pathway has potential to limit viral replication. Mechanistically, S312 binds at the putative ubiquinone binding tunnel within the DHODH active site.
iupac name: 2-[(Z)-[[4-(2-chlorophenyl)-1,3-thiazol-2-yl]hydrazinylidene]methyl]benzoic acid
synonym: compound 19 [PMID: 26443076]
approved: f
ligand name: S312
type: SyntheticOrganicLigand

WM382
in ch i key: ZSZSSSHEMYULPX-FCHUYYIVSA-N
in ch i: InChI=1S/C29H36N4O4/c1-5-29(6-2)17-25(34)33(27(30)32-29)22-13-14-36-23-12-11-18(15-20(22)23)26(35)31-21-16-28(3,4)37-24-10-8-7-9-19(21)24/h7-12,15,21-22H,5-6,13-14,16-17H2,1-4H3,(H2,30,32)(H,31,35)/t21-,22+/m0/s1
comment: WM382 is the drug-like lead for a novel class of antimalarial compounds that are dual inhibitors of P. falciparum plasmepsin IX (PfPMIX) and plasmepsin X (PfPMX). The compound was identified by an optimization study following phenotypic high-throughput screening of an aspartic protease inhibitor library <Reference id=40135/>. The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
iupac name: (4R)-4-(2-amino-4,4-diethyl-6-oxo-5H-pyrimidin-1-yl)-N-[(4S)-2,2-dimethyl-3,4-dihydrochromen-4-yl]-3,4-dihydro-2H-chromene-6-carboxamide
approved: f
ligand name: WM382
type: SyntheticOrganicLigand

ORM-10962
in ch i key: UPGUBLDTYLMRHO-UHFFFAOYSA-N
in ch i: InChI=1S/C27H29N3O4/c31-22-12-14-30(15-13-22)18-26(32)29-21-7-11-27(28-17-21)33-23-8-10-25-20(16-23)6-9-24(34-25)19-4-2-1-3-5-19/h1-5,7-8,10-11,16-17,22,24,31H,6,9,12-15,18H2,(H,29,32)
comment: ORM-10962 is a selective inhibitor of the SCL8 (NCX) Na+/Ca2+ exchangers <Reference id=40093/>. It blocks both inward and outward NCX currents. ORM-10962 has been used in vivo to demonstrate that NCX blockade may contribute to the prevention of delayed afterdepolarization-based arrhythmogenesis.
iupac name: 2-(4-hydroxypiperidin-1-yl)-N-[6-[(2-phenyl-3,4-dihydro-2H-chromen-6-yl)oxy]pyridin-3-yl]acetamide
synonym: ORM10962
approved: f
ligand name: ORM-10962
type: SyntheticOrganicLigand

neurounina-1
canonical SMILES: O=C1CN=C(c2c(N1CN1CCCC1)ccc(c2)[N+](=O)[O-])c1ccccc1
isomeric SMILES: O=C1CN=C(c2c(N1CN1CCCC1)ccc(c2)[N+](=O)[O-])c1ccccc1
in ch i key: CUVPPONHRDLGFB-UHFFFAOYSA-N
in ch i: InChI=1S/C20H20N4O3/c25-19-13-21-20(15-6-2-1-3-7-15)17-12-16(24(26)27)8-9-18(17)23(19)14-22-10-4-5-11-22/h1-3,6-9,12H,4-5,10-11,13-14H2
comment: Neurounina-1 increases activity of the NCX1 and NCX2 SLC8 Na+/Ca2+ exchangers <Reference id=40094/>. It effectively protects against stroke damage in vivo.
iupac name: 7-nitro-5-phenyl-1-(pyrrolidin-1-ylmethyl)-3H-1,4-benzodiazepin-2-one
approved: f
ligand name: neurounina-1
type: SyntheticOrganicLigand

compound 3 [PMID: 32636746]
in ch i key: ZTCLCSCHTACERP-AWEZNQCLSA-N
comment: Compound 3 is a small molecule B2 receptor antagonist that was a precursor for the design and development of the first-in-class, Phase 1 clinical lead PHA-022121 (Pharvaris) <Reference id=40058/>. PHA-022121 is being developed as an oral drug for treatment and prevention of acute hereditary angioedema (HAE) attacks.
iupac name: N-[(1S)-1-[3-chloro-5-fluoro-2-[[2-methyl-4-(2-methyl-1,2,4-triazol-3-yl)quinolin-8-yl]oxymethyl]phenyl]ethyl]-2-(difluoromethoxy)acetamide
synonym: example 6 [WO2019101906]
approved: f
ligand name: compound 3 [PMID: 32636746]
type: SyntheticOrganicLigand

compound 18 [PMID: 32330443]
in ch i key: ZSOFJUIAJLLJBK-CXUHLZMHSA-N
in ch i: InChI=1S/C29H27NO7/c1-16(15-35-26(34)17-6-5-11-30-14-17)9-10-28-25(33)18-12-19-24(32)23-20(31)7-4-8-21(23)36-29(19,28)22(13-18)27(2,3)37-28/h4-9,11-12,14,18,22,31H,10,13,15H2,1-3H3/b16-9+
comment: SPTSSB (serine palmitoyltransferase small subunit B) inhibitor <Reference id=40041/>.
iupac name: (E)-4-(8-hydroxy-2,2-dimethyl-4,7-dioxo-1,2,5,7-tetrahydro-1,5-methanofuro[2,3-d]xanthen-3a(4H)-yl)-2-methylbut-2-en-1-yl nicotinate
approved: f
ligand name: compound 18 [PMID: 32330443]
type: SyntheticOrganicLigand

compound 8ay [PMID: 29589443]
in ch i key: JTZBKOVVHITLRP-UHFFFAOYSA-N
comment: Kidney Urea Transporter UT-A1 inhibitor.
iupac name: 5-chloro-2-methoxy-N-[4-({1-propyl-[1,2,4]triazolo[4,3-a]quinoxalin-4-yl}oxy)phenyl]benzene-1-sulfonamide
approved: f
ligand name: compound 8ay [PMID: 29589443]
type: SyntheticOrganicLigand

compound 5 [Stecula et al., 2020]
in ch i key: HMEXVJMBPXPLKN-UHFFFAOYSA-N
comment: Compound 5 was reported as a low-molecular-weight inhibitor of the Helicobacter pylori protein flavodoxin, with antibacterial activity against this pathogen, in 2013 <Reference id=40034/>. A 2020 report by Stecula et al. found that compound 5 inhibits the novel disease target aspartate N-acetyltransferase (ANAT; NAT8L), and that 5 offers a tool compound, with a suitably drug-like scaffold, for studying ANAT inhibition as a therapeutic approach in Canavan disease <Reference id=40033/>.
xref: CHEMBL2409288
synonym: MCULE-2879769428
approved: f
ligand name: compound 5 [Stecula et al., 2020]
type: SyntheticOrganicLigand

phenelzine
canonical SMILES: NNCCc1ccccc1
isomeric SMILES: NNCCc1ccccc1
in ch i key: RMUCZJUITONUFY-UHFFFAOYSA-N
in ch i: InChI=1S/C8H12N2/c9-10-7-6-8-4-2-1-3-5-8/h1-5,10H,6-7,9H2
comment: Phenelzine is a monoamine oxidase inhibitor (MAOI).
iupac name: (2-phenylethyl)hydrazine
xref: CHEMBL1089
synonym: Nardil®
synonym: phenelzine sulfate
approved: t
ligand name: phenelzine
type: SyntheticOrganicLigand

AB928
in ch i key: BUXIAWLTBSXYSW-UHFFFAOYSA-N
in ch i: InChI=1S/C23H22N8O/c1-14-15(11-24)6-4-8-17(14)18-10-19(28-22(25)27-18)20-13-31(30-29-20)12-16-7-5-9-21(26-16)23(2,3)32/h4-10,13,32H,12H2,1-3H3,(H2,25,27,28)
comment: AB928 is an oral dual antagonist of the adenosine 2A and 2B receptor isoforms <Reference id=36724/>. It was developed to counteract adenosine-mediated immune suppression in the tumour microenvironment by targeting A2AR-expressing T and NK cells and A2A/2BR-expressing myeloid cells.
iupac name: 3-[2-amino-6-[1-[[6-(2-hydroxypropan-2-yl)pyridin-2-yl]methyl]triazol-4-yl]pyrimidin-4-yl]-2-methylbenzonitrile
synonym: AB-928
approved: f
ligand name: AB928
type: SyntheticOrganicLigand

imaradenant
canonical SMILES: Nc1nnc(c(n1)c1ccc(cc1)F)c1cc(C)nc(c1)Cl
isomeric SMILES: Nc1nnc(c(n1)c1ccc(cc1)F)c1cc(C)nc(c1)Cl
in ch i key: NCWQLHHDGDXIJN-UHFFFAOYSA-N
in ch i: InChI=1S/C15H11ClFN5/c1-8-6-10(7-12(16)19-8)14-13(20-15(18)22-21-14)9-2-4-11(17)5-3-9/h2-7H,1H3,(H2,18,20,22)
comment: Imaradenant (AZD4635) is an orally bioavailable adenosine A2A receptor (A2AR) antagonist <Reference id=40026/>. It was developed as a potential immuno-oncology (immunotherapy) drug. Imaradenant reduces the immunosuppressive effects of adenosine within the tumour microenvironment, an activity that rescues immune cell function and it enhances the efficacy of checkpoint inhibitors in syngeneic mouse tumour models <Reference id=40026/>. In 2021 AstraZeneca decided to stop a number of their midphase studies of imaradenant in patients with prostate cancer.
synonym: AZD-4635
synonym: AZD4635
approved: f
ligand name: imaradenant
type: SyntheticOrganicLigand

abacavir
in ch i key: MCGSCOLBFJQGHM-SCZZXKLOSA-N
in ch i: InChI=1S/C14H18N6O/c15-14-18-12(17-9-2-3-9)11-13(19-14)20(7-16-11)10-4-1-8(5-10)6-21/h1,4,7-10,21H,2-3,5-6H2,(H3,15,17,18,19)/t8-,10+/m1/s1
comment: Abacavir is a nucleoside analogue reverse transcriptase inhibitor (NRTI) class antiretroviral drug.
iupac name: [(1S,4R)-4-[2-amino-6-(cyclopropylamino)purin-9-yl]-1-cyclopent-2-enyl]methanol
xref: CHEMBL1380
synonym: Ziagen®
synonym: 1592U89
approved: t
ligand name: abacavir
type: SyntheticOrganicLigand

ML2-SA1
canonical SMILES: Clc1cccc(c1C1=NOC2C1C1CCC2C1)Cl
isomeric SMILES: Clc1cccc(c1C1=NOC2C1C1CCC2C1)Cl
in ch i key: NBXVMFMMTKYFQP-UHFFFAOYSA-N
in ch i: InChI=1S/C14H13Cl2NO/c15-9-2-1-3-10(16)12(9)13-11-7-4-5-8(6-7)14(11)18-17-13/h1-3,7-8,11,14H,4-6H2
comment: ML2-SA1 is a selective agonist of TRPML2-mediated ion currents <Reference id=37322/>.
synonym: EVP22
synonym: EVP-22
synonym: ML2SA1
synonym: ML2 SA1
approved: f
ligand name: ML2-SA1
type: SyntheticOrganicLigand

GSK1795091
in ch i key: ICLAYQQKWJGHBV-XJZMHMBSSA-N
comment: GSK1795091 is a dendritic glycolipid TLR4 agonist with potential immunoadjuvant activity <Reference id=40018/><Reference id=40019/>. Structurally it is a mimetic of bacterial lipid A <Reference id=40020/>. TLR4 plays a key role in the activation of the innate immune response. Activating TLR4 stimulates dendritic cells (DCs), monocytes and macrophages to increase production of pro-inflammatory cytokines (IFNγ, TNFα, interleukins (IL), IL-1 beta, -6 and -12). This mechanism produces a Th1 immune response that offers adjuvant potential in combination with tumour antigen vaccines, and a subsequent cytotoxic T-lymphocyte response against the targeted tumour cells. It also enhances the immune response to checkpoint inhibitor cancer therapies.
xref: CHEMBL507938
synonym: CRX-601
synonym: CRX601
synonym: GSK-1795091
synonym: GSK'091
synonym: compound 4 [PMID: 18835160]
approved: f
ligand name: GSK1795091
type: SyntheticOrganicLigand

GW405833
in ch i key: FSFZRNZSZYDVLI-UHFFFAOYSA-N
comment: Selective, high affinity CB2 receptor partial agonist.
iupac name: (2,3-dichlorophenyl)-[5-methoxy-2-methyl-3-(2-morpholin-4-ylethyl)indol-1-yl]methanone
synonym: GW 405833
synonym: GW-405833
synonym: L-768,242
synonym: L768242
approved: f
ligand name: GW405833
type: SyntheticOrganicLigand

compound 8 [Avgoustou et al., 2020]
in ch i key: CKZLNCWDRQNNEQ-WJOKGBTCSA-N
in ch i: InChI=1S/C31H35N5O3/c1-30(2,3)29(39)36(18-22-9-6-5-8-21(22)17-32-4)19-26(37)34-24-12-11-20-15-31(16-23(20)14-24)25-10-7-13-33-27(25)35-28(31)38/h5-14,32H,15-19H2,1-4H3,(H,34,37)(H,33,35,38)/t31-/m1/s1
comment: Potent AM2 receptor (Adrenomedullin-2 Receptor) antagonist <Reference id=40015/>.
iupac name: 2,2-dimethyl-N-[[2-(methylaminomethyl)phenyl]methyl]-N-[2-oxo-2-[[(2R)-2'-oxospiro[1,3-dihydroindene-2,3'-1H-pyrrolo[2,3-b]pyridine]-5-yl]amino]ethyl]propanamide
approved: f
ligand name: compound 8 [Avgoustou et al., 2020]
type: SyntheticOrganicLigand

compound 60 [PMID: 30889352]
in ch i key: MHOHZJCELKBJCZ-XMMPIXPASA-N
in ch i: InChI=1S/C26H28ClNO2S/c27-23-12-10-22(11-13-23)19-31-26-5-1-4-25(15-26)30-18-21-8-6-20(7-9-21)16-28-14-2-3-24(28)17-29/h1,4-13,15,24,29H,2-3,14,16-19H2/t24-/m1/s1
comment: Compound 60 is a sphingosine kinase inhibitor, with selectivity for the SPHK2 isoform <Reference id=40006/>.
approved: f
ligand name: compound 60 [PMID: 30889352]
type: SyntheticOrganicLigand

compound 59 [PMID: 30889352]
in ch i key: IOSLINNLJFQMFF-XMMPIXPASA-N
in ch i: InChI=1S/C26H28FNO2S/c27-23-12-10-22(11-13-23)19-31-26-5-1-4-25(15-26)30-18-21-8-6-20(7-9-21)16-28-14-2-3-24(28)17-29/h1,4-13,15,24,29H,2-3,14,16-19H2/t24-/m1/s1
comment: Compound 59 is sphingosine kinase inhibitor <Reference id=40006/>. It exhibits some selectivity for SPHK2.
approved: f
ligand name: compound 59 [PMID: 30889352]
type: SyntheticOrganicLigand

compound 55 [PMID: 30889352]
in ch i key: YYCORJSTUXRKOM-XMMPIXPASA-N
in ch i: InChI=1S/C26H28ClNO3/c27-23-12-10-22(11-13-23)19-31-26-5-1-4-25(15-26)30-18-21-8-6-20(7-9-21)16-28-14-2-3-24(28)17-29/h1,4-13,15,24,29H,2-3,14,16-19H2/t24-/m1/s1
comment: Compound 55 is sphingosine kinase inhibitor <Reference id=40006/>. It is selective for SPHK2.
approved: f
ligand name: compound 55 [PMID: 30889352]
type: SyntheticOrganicLigand

compound 49 [PMID: 30889352]
in ch i key: SPXSEZMVRJLHQG-XMMPIXPASA-N
in ch i: InChI=1S/C26H29NO3/c28-18-24-8-5-15-27(24)17-21-11-13-23(14-12-21)20-30-26-10-4-9-25(16-26)29-19-22-6-2-1-3-7-22/h1-4,6-7,9-14,16,24,28H,5,8,15,17-20H2/t24-/m1/s1
comment: Compound 49 is sphingosine kinase inhibitor <Reference id=40006/>. It is equipotent at both isoforms, SPHK1 and SPHK2.
approved: f
ligand name: compound 49 [PMID: 30889352]
type: SyntheticOrganicLigand

alizapride
canonical SMILES: C=CCN1CCCC1CNC(=O)c1cc2[nH]nnc2cc1OC
isomeric SMILES: C=CCN1CCCC1CNC(=O)c1cc2[nH]nnc2cc1OC
in ch i key: KSEYRUGYKHXGFW-UHFFFAOYSA-N
in ch i: InChI=1S/C16H21N5O2/c1-3-6-21-7-4-5-11(21)10-17-16(22)12-8-13-14(19-20-18-13)9-15(12)23-2/h3,8-9,11H,1,4-7,10H2,2H3,(H,17,22)(H,18,19,20)
comment: Dopamine D2 receptor antagonist with prokinetic and antiemetic effects which can also be used in the treatment of nausea and vomiting, including postoperative nausea and vomiting. The WHO INN record for alizapride provides the CAS registry number 59338-93-1. This CAS number maps to PubChem CID 135413504 (vergentan), which is a tautomer of alizapride.
iupac name: 6-methoxy-N-[(1-prop-2-enylpyrrolidin-2-yl)methyl]-2H-benzotriazole-5-carboxamide
synonym: Limican®
synonym: Litican®
synonym: Nausilex®
synonym: Plitican®
synonym: Superan®
synonym: Vergentan®
approved: t
ligand name: alizapride
type: SyntheticOrganicLigand

metopimazine
in ch i key: BQDBKDMTIJBJLA-UHFFFAOYSA-N
in ch i: InChI=1S/C22H27N3O3S2/c1-30(27,28)17-7-8-21-19(15-17)25(18-5-2-3-6-20(18)29-21)12-4-11-24-13-9-16(10-14-24)22(23)26/h2-3,5-8,15-16H,4,9-14H2,1H3,(H2,23,26)
comment: Dopamine D2 receptor antagonist. Approved for clinical use as an antiemetic agent.
iupac name: 1-[3-(2-methylsulfonylphenothiazin-10-yl)propyl]piperidine-4-carboxamide
xref: CHEMBL398615
synonym: RP-9965
synonym: EXP-999
synonym: NG-101
synonym: Vogalene®
approved: t
ligand name: metopimazine
type: SyntheticOrganicLigand

favipiravir
canonical SMILES: Fc1c[nH]c(=O)c(n1)C(=O)N
isomeric SMILES: Fc1c[nH]c(=O)c(n1)C(=O)N
in ch i key: ZCGNOVWYSGBHAU-UHFFFAOYSA-N
in ch i: InChI=1S/C5H4FN3O2/c6-2-1-8-5(11)3(9-2)4(7)10/h1H,(H2,7,10)(H,8,11)
comment: Favipiravir (T-705) is an orally delivered, guanine (purine) analogue antiviral drug (cf. <Ligand id=10715/> which is administered i.v.). It targets viral RNA-dependent RNA polymerase (RdRP) of RNA viruses and since the catalytic domain of RdRP is well conserved across species, has a broad-spectrum of activity; although Furuta et al. (2002) reported that actvity was weak against non-influenza virus RNA viruses <Reference id=39980/>. Favipiravir was originally identified through a chemical library screen against influenza virus RdRP <Reference id=39993/>. Chemically, it is a prodrug. In human cells it undergoes phosphoribosylation and phosphorylation to its active form, favipiravir-ribofuranosyl-5′-triphosphate (F-RTP). F-RTP is bound by the RdRP, but it blocks enzyme activity and so terminates chain elongation <Reference id=39994/><Reference id=39995/>.
iupac name: 5-fluoro-2-oxo-1H-pyrazine-3-carboxamide
xref: CHEMBL221722
synonym: T-705
synonym: T705
approved: t
ligand name: favipiravir
type: SyntheticOrganicLigand

ASN008
in ch i key: MSOHOVLMACCLHW-XMMPIXPASA-N
in ch i: InChI=1S/C25H35N2/c1-20-10-4-7-14-25(20)26(16-15-24-13-8-9-17-27(24,2)3)23-18-21-11-5-6-12-22(21)19-23/h4-7,10-12,14,23-24H,8-9,13,15-19H2,1-3H3/q+1/t24-/m1/s1
comment: Permanently charged sodium channel blocker. This entry shows the compound without the associated bromide ion <Reference id=39885/>. In human clinical trials as a topical gel for the treatment of pruritus (itch) associated with atopic dermatitis.
iupac name: N-[2-[(2R)-1,1-dimethylpiperidin-1-ium-2-yl]ethyl]-N-(2-methylphenyl)-2,3-dihydro-1H-inden-2-amine
approved: f
ligand name: ASN008
type: SyntheticOrganicLigand

atazanavir
in ch i key: AXRYRYVKAWYZBR-GASGPIRDSA-N
in ch i: InChI=1S/C38H52N6O7/c1-37(2,3)31(41-35(48)50-7)33(46)40-29(22-25-14-10-9-11-15-25)30(45)24-44(43-34(47)32(38(4,5)6)42-36(49)51-8)23-26-17-19-27(20-18-26)28-16-12-13-21-39-28/h9-21,29-32,45H,22-24H2,1-8H3,(H,40,46)(H,41,48)(H,42,49)(H,43,47)/t29-,30-,31+,32+/m0/s1
comment: Atazanavir is a human immunodeficiency virus 1 (HIV-1) protease inhibitor (PI) <Reference id=39981/>.
iupac name: methyl N-[(2S)-1-[[(2S,3S)-3-hydroxy-4-[[[(2S)-2-(methoxycarbonylamino)-3,3-dimethylbutanoyl]amino]-[(4-pyridin-2-ylphenyl)methyl]amino]-1-phenylbutan-2-yl]amino]-3,3-dimethyl-1-oxobutan-2-yl]carbamate
xref: CHEMBL1163
synonym: Reyataz®
synonym: latazanavir
synonym: zrivada
synonym: BMS-232632
synonym: BMS 232632
synonym: CGP 73547
synonym: CGP-73547
approved: t
ligand name: atazanavir
type: SyntheticOrganicLigand

seladelpar
in ch i key: JWHYSEDOYMYMNM-QGZVFWFLSA-N
in ch i: InChI=1S/C21H23F3O5S/c1-3-27-17(11-28-16-6-4-15(5-7-16)21(22,23)24)13-30-18-8-9-19(14(2)10-18)29-12-20(25)26/h4-10,17H,3,11-13H2,1-2H3,(H,25,26)/t17-/m1/s1
comment: Seladelpar (MBX-8025) is a clinical stage, selective PPARδ agonist <Reference id=39966/> that was initially developed as a therapy for atherogenic dyslipidemia and nonalcoholic steatohepatitis (NASH).
iupac name: 2-[4-[(2R)-2-ethoxy-3-[4-(trifluoromethyl)phenoxy]propyl]sulfanyl-2-methylphenoxy]acetic acid
xref: CHEMBL230158
synonym: MBX-8025
synonym: MBX8025
synonym: compound 3r [PMID: 17524639]
approved: f
ligand name: seladelpar
type: SyntheticOrganicLigand

MC2050
in ch i key: AFXJUCILCGBUNX-UHFFFAOYSA-N
in ch i: InChI=1S/C19H21N5OS/c25-18-15-5-1-2-6-16(15)21-19(22-18)26-14-13-23-9-11-24(12-10-23)17-7-3-4-8-20-17/h1-8H,9-14H2,(H,21,22,25)
comment: MC2050 is a poly(ADP-ribose) polymerase (PARP) inhibitor that is selective for PARP1 over PARP2 <Reference id=38803/>. As the dihydrochloride salt it is water soluble. MC2050 interacts with both the nicotinamide and adenine ribose binding sites within the enzyme's catalytic domain.
iupac name: 2-[2-(4-pyridin-2-ylpiperazin-1-yl)ethylsulfanyl]-3H-quinazolin-4-one
approved: f
ligand name: MC2050
type: SyntheticOrganicLigand

almonertinib
in ch i key: DOEOECWDNSEFDN-UHFFFAOYSA-N
in ch i: InChI=1S/C30H35N7O2/c1-6-29(38)32-24-17-25(28(39-5)18-27(24)36(4)16-15-35(2)3)34-30-31-14-13-23(33-30)22-19-37(20-11-12-20)26-10-8-7-9-21(22)26/h6-10,13-14,17-20H,1,11-12,15-16H2,2-5H3,(H,32,38)(H,31,33,34)
comment: Almonertinib (HS-10296) is an orally bioavailable, third generation inhibitor of the receptor tyrosine kinase epidermal growth factor receptor (EGFR) with activity at the EGFRT790M mutant <Reference id=39963/>. In assays using triple-negative breast cancer MDA-MB-231 cells, HS-10296 inhibits signalling via the EGFR/PI3K/AKT pathway which results in reduced proliferation and induction of autophagy and apoptosis. HS-10296 was developed by Hansoh Pharmaceutical, and ex-China rights were licensed to EQRx in mid-2020.
iupac name: N-[5-[[4-(1-cyclopropylindol-3-yl)pyrimidin-2-yl]amino]-2-[2-(dimethylamino)ethyl-methylamino]-4-methoxyphenyl]prop-2-enamide
synonym: almonertinib
synonym: HS10296
synonym: Ameile
synonym: Egfr T790M inhibitor HS-10296
synonym: example 26 [WO2016054987A1]
approved: t
ligand name: almonertinib
type: SyntheticOrganicLigand

elafibranor
canonical SMILES: CSc1ccc(cc1)C(=O)/C=C/c1cc(C)c(c(c1)C)OC(C(=O)O)(C)C
isomeric SMILES: CSc1ccc(cc1)C(=O)/C=C/c1cc(C)c(c(c1)C)OC(C(=O)O)(C)C
in ch i key: AFLFKFHDSCQHOL-IZZDOVSWSA-N
in ch i: InChI=1S/C22H24O4S/c1-14-12-16(13-15(2)20(14)26-22(3,4)21(24)25)6-11-19(23)17-7-9-18(27-5)10-8-17/h6-13H,1-5H3,(H,24,25)/b11-6+
comment: Elafibranor (GFT-505) is a PPARα/δ agonist. It was taken into clinical development by Genfit, as a therapuetic for nonalcoholic steatohepatitis (NASH) <Reference id=39959/>. Genfit terminated development at Phase 3 in mid-2020 following futility analysis. Dual PPARα/δ agonists are also referred to as 'glitazars'.
iupac name: 2-[2,6-dimethyl-4-[(E)-3-(4-methylsulfanylphenyl)-3-oxoprop-1-enyl]phenoxy]-2-methylpropanoic acid
xref: CHEMBL3707395
synonym: GFT-505
synonym: GFT505
approved: f
ligand name: elafibranor
type: SyntheticOrganicLigand

TTT-3002
in ch i key: DCAYZGCTSXLIHO-FYCNXDEQSA-N
in ch i: InChI=1S/C27H23N5O3/c1-26-27(28,25(34)29-2)11-18(35-26)31-16-9-5-3-7-13(16)20-21-15(12-30-24(21)33)19-14-8-4-6-10-17(14)32(26)23(19)22(20)31/h3-10,18H,11-12,28H2,1-2H3,(H,29,34)(H,30,33)/t18-,26+,27-/m0/s1
comment: TTT-3002 is an experimental indolocarbazole kinase inhibitor. It was originally reported as a LRRK2 inhibitor (including activity against the G2019S and R1441C mutations) <Reference id=39957/>. Subsequent analysis revealed that TTT-3002 overcomes activating and drug resistance mutations in FLT3 in acute myeloid leukemia cells <Reference id=39956/> and is active against FLT3-associated leukemias in vitro and in vivo <Reference id=39955/>.
synonym: TTT3002
approved: f
ligand name: TTT-3002
type: SyntheticOrganicLigand

AMG-232
in ch i key: DRLCSJFKKILATL-YWCVFVGNSA-N
comment: AMG-232 is a clinical stage orally available inhibitor of MDM2 <Reference id=39951/>, that was designed for anti-tumour potential. It disrupts the MDM2-p53 interaction.
iupac name: 2-[(3R,5R,6S)-5-(3-chlorophenyl)-6-(4-chlorophenyl)-3-methyl-1-[(2S)-3-methyl-1-propan-2-ylsulfonylbutan-2-yl]-2-oxopiperidin-3-yl]acetic acid
xref: CHEMBL3125702
synonym: AMG232
synonym: KRT-232
synonym: KRT232
synonym: compound 2 [PMID: 24456472]
approved: f
ligand name: AMG-232
type: SyntheticOrganicLigand

compound 25 [PMID: 32687365]
in ch i key: SPZFHDGEKBUECT-UHFFFAOYSA-N
comment: Compound 25 is a dual agonist of the ligand-activated transcription factors, farnesoid X receptor (FXR) and peroxisome proliferator-activated receptor (PPAR) δ <Reference id=39936/> . It was designed to explore the potential of simultaneous activation of peripheral PPARδ-mediated activity and hepatic FXR mechanisms for the treatment of nonalcoholic steatohepatitis (NASH).
iupac name: 2-(4-((2-Chloro-4-((3-(2,6-dichlorophenyl)-5-isopropylisoxazol-4-yl)methoxy)benzyl)amino)phenyl)acetic acid
approved: f
ligand name: compound 25 [PMID: 32687365]
type: SyntheticOrganicLigand

clavulanic acid
canonical SMILES: OC(=O)[C@@H]1N2[C@H](O/C/1=C/CO)CC2=O
isomeric SMILES: OC(=O)[C@@H]1N2[C@H](O/C/1=C/CO)CC2=O
in ch i key: HZZVJAQRINQKSD-PBFISZAISA-N
in ch i: InChI=1S/C8H9NO5/c10-2-1-4-7(8(12)13)9-5(11)3-6(9)14-4/h1,6-7,10H,2-3H2,(H,12,13)/b4-1-/t6-,7-/m1/s1
comment: Clavulanic acid is a β-lactamase inhibitor that was isolated from Streptomyces clavuligerusi. It is used in combination with β-lactam antibacterials and does not have inherent antibacterial activity. Clavulanic acid can overcome antibacterial resistance in bacteria that secrete β-lactamase. In the WHO Essential Medicines list as the mixture of amoxicillin + clavulanic acid (co-amoxiclav).
iupac name: (2R,3Z,5R)-3-(2-hydroxyethylidene)-7-oxo-4-oxa-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
xref: CHEMBL777
synonym: BRL14151
synonym: BRL-14151
synonym: BRL-14151K
synonym: clavulanate
approved: t
ligand name: clavulanic acid
type: SyntheticOrganicLigand

spectinomycin
in ch i key: UNFWWIHTNXNPBV-WXKVUWSESA-N
in ch i: InChI=1S/C14H24N2O7/c1-5-4-6(17)14(20)13(21-5)22-12-10(19)7(15-2)9(18)8(16-3)11(12)23-14/h5,7-13,15-16,18-20H,4H2,1-3H3/t5-,7-,8+,9+,10+,11-,12-,13+,14+/m1/s1
comment: Spectinomycin is an aminocyclitol aminoglycoside bacteriostatic antibacterial. It was isolated from Streptomyces spectabilis. Spectinomycin is active against gram-negative bacteria.
xref: CHEMBL1167
synonym: M-141
synonym: U18409
synonym: U-18409
synonym: U-18409E
synonym: Trobicin®
approved: t
ligand name: spectinomycin
type: NaturalProductLigand

bindarit
canonical SMILES: OC(=O)C(OCc1nn(c2c1cccc2)Cc1ccccc1)(C)C
isomeric SMILES: OC(=O)C(OCc1nn(c2c1cccc2)Cc1ccccc1)(C)C
in ch i key: MTHORRSSURHQPZ-UHFFFAOYSA-N
in ch i: InChI=1S/C19H20N2O3/c1-19(2,18(22)23)24-13-16-15-10-6-7-11-17(15)21(20-16)12-14-8-4-3-5-9-14/h3-11H,12-13H2,1-2H3,(H,22,23)
comment: Bindarit is a compound with anti-inflammatory activity. In vitro, that is primarily associated with an inhibition of MCP-1 (CCL2) production and subsequent reduction in monocyte recruitment and differentiation. It has been shown to directly interact with fatty acid binding protein 4 (FABP4) and this is proposed to underlie its mechanism of action <Reference id=39916/>. In this mechanism bindarit modulates the phosphorylation state of p38α and AKT2 and selectively increases FABP4 expression, all in a PPARγ-dependent manner, and these effects are associated with a decrease in MCP-1 production.
iupac name: 2-[(1-benzylindazol-3-yl)methoxy]-2-methylpropanoic acid
xref: CHEMBL2107549
synonym: AF2838
synonym: AF-2838
approved: f
ligand name: bindarit
type: SyntheticOrganicLigand

MC1568
canonical SMILES: ONC(=O)/C=C/c1cc(cn1C)/C=C/C(=O)c1cccc(c1)F
isomeric SMILES: ONC(=O)/C=C/c1cc(cn1C)/C=C/C(=O)c1cccc(c1)F
in ch i key: QRDAPCMJAOQZSU-KQQUZDAGSA-N
in ch i: InChI=1S/C17H15FN2O3/c1-20-11-12(9-15(20)6-8-17(22)19-23)5-7-16(21)13-3-2-4-14(18)10-13/h2-11,23H,1H3,(H,19,22)/b7-5+,8-6+
comment: MC1568 is an inhibitor of class IIa (HDAC4, HDAC5, HDAC6, HDAC7 and HDAC9) and IIb (HDAC6 and HDAC10) histone deacetylases (HDACs) <Reference id=39905/>.
xref: CHEMBL191089
synonym: HDAC-IN-1
synonym: MC-1568
synonym: compound 2f [PMID: 15857140]
approved: f
ligand name: MC1568
type: SyntheticOrganicLigand

ACY-738
canonical SMILES: ONC(=O)c1cnc(nc1)NC1(CC1)c1ccccc1
isomeric SMILES: ONC(=O)c1cnc(nc1)NC1(CC1)c1ccccc1
in ch i key: LIIWIMDSZVNYHY-UHFFFAOYSA-N
in ch i: InChI=1S/C14H14N4O2/c19-12(18-20)10-8-15-13(16-9-10)17-14(6-7-14)11-4-2-1-3-5-11/h1-5,8-9,20H,6-7H2,(H,18,19)(H,15,16,17)
comment: ACY-738 is an orally-bioavailable histone deacetylase (HDAC) inhibitor <Reference id=39903/><Reference id=34729/>. It has some selectivity for HDAC6.
xref: CHEMBL3655950
synonym: example 73 [WO2012068109A2]
approved: f
ligand name: ACY-738
type: SyntheticOrganicLigand

bavarostat
in ch i key: IGZQZELTOHAHNW-UHFFFAOYSA-N
in ch i: InChI=1S/C20H27FN2O2/c1-23(11-17-3-2-16(7-18(17)21)19(24)22-25)12-20-8-13-4-14(9-20)6-15(5-13)10-20/h2-3,7,13-15,25H,4-6,8-12H2,1H3,(H,22,24)
comment: Bavarostat is a histone deacetylase inhibitor with selectivity for the HDAC6 isoform <Reference id=39902/>.
xref: CHEMBL4165724
synonym: compound 4 [PMID: 30118224]
approved: f
ligand name: bavarostat
type: SyntheticOrganicLigand

martinostat
canonical SMILES: ONC(=O)/C=C/c1ccc(cc1)CN(CC12CC3CC(C2)CC(C1)C3)C
isomeric SMILES: ONC(=O)/C=C/c1ccc(cc1)CN(CC12CC3CC(C2)CC(C1)C3)C
in ch i key: WNIDBXBLQFPAJA-VOTSOKGWSA-N
in ch i: InChI=1S/C22H30N2O2/c1-24(14-17-4-2-16(3-5-17)6-7-21(25)23-26)15-22-11-18-8-19(12-22)10-20(9-18)13-22/h2-7,18-20,26H,8-15H2,1H3,(H,23,25)/b7-6+
comment: Martinostat is an inhibitor of class I HDACs (HDACs 1-3) and class IIb HDAC6. A [11C] radio-isotope-labelled version has been developed for PET imaging <Reference id=39901/>.
synonym: compound 6 [PMID: 25203558]
approved: f
ligand name: martinostat
type: SyntheticOrganicLigand

X-165
in ch i key: CDSKRHGFXHZEQL-JOCHJYFZSA-N
in ch i: InChI=1S/C28H28F4N6O4/c1-15(2)22(34-23(39)19-13-17(28(30,31)32)4-6-20(19)29)24(40)37-10-8-27(9-11-37)25(41)36(3)26(42)38(27)18-5-7-21-16(12-18)14-33-35-21/h4-7,12-15,22H,8-11H2,1-3H3,(H,33,35)(H,34,39)/t22-/m1/s1
comment: X-165 is a potent, selective, and bioavailable small molecule inhibitor of the LPA synthetic phosphodiesterase, autotaxin <Reference id=39878/>. Autotaxin inhibitors are investigated for their anti-fibrotic potential, and X-165 was developed for potential to treat idiopathic pulmonary fibrosis (IPF). Analysis of autotaxin/X-165 complex crystals revealed that this compound binds to a site on the enzyme that is distinct from the binding site of exisiting inhibitors. Its binding pose shares some similarity with that of <Ligand id=9561/> (GLPG1690), but retains crucial differences.
iupac name: (R)-N-(1-(1-(1H-Indazol-5-yl)-3-methyl-2,4-dioxo-1,3,8-triazaspiro[4.5]decan-8-yl)-3-methyl-1-oxobutan-2-yl)-2-fluoro-5-(trifluoromethyl)benzamide
synonym: compound 1 [PMID: 32584034]
synonym: X165
approved: f
ligand name: X-165
type: SyntheticOrganicLigand

DCLK1-IN-1
in ch i key: OQFCHSFVWSLDAO-UHFFFAOYSA-N
in ch i: InChI=1S/C26H28F3N7O2/c1-33-10-12-35(13-11-33)17-8-9-19(22(14-17)38-3)31-25-30-15-21-23(32-25)34(2)20-7-5-4-6-18(20)24(37)36(21)16-26(27,28)29/h4-9,14-15H,10-13,16H2,1-3H3,(H,30,31,32)
comment: DCLK1-IN-1 is reported as a selective inhibitor of the serine/threonine kinases, doublecortin-like kinase 1 and 2 <Reference id=39876/><Reference id=39877/>. It was discovered using chemoproteomic profiling and structure-based design, and is an in vivo suitable tool for investigating and characterizing the physiological and pathophysiological roles of these kinases, particularly the role of DCLK1 in cancer and type II immunity in the gut (via epithelial tuft cells). DCLK1-IN-1 shares a chemical scaffold with <Ligand id=9396/> (an LRRK2 inhibitor) and <Ligand id=8057/> (an ERK5 inhibitor) which both exhibit off-target activity towards DCLK1. These latter tool compounds also inhibit the bromodomains of the oncology target BRD4. DCLK1-IN-1 was designed to reduce off-target effects and increase DCLK1 selectivity.
iupac name: 2-[2-methoxy-4-(4-methylpiperazin-1-yl)anilino]-11-methyl-5-(2,2,2-trifluoroethyl)pyrimido[4,5-b][1,4]benzodiazepin-6-one
synonym: compound 4 [PMID: 32251410]
approved: f
ligand name: DCLK1-IN-1
type: SyntheticOrganicLigand

fostemsavir
in ch i key: SWMDAPWAQQTBOG-UHFFFAOYSA-N
in ch i: InChI=1S/C25H26N7O8P/c1-16-27-14-32(28-16)23-21-20(19(39-2)12-26-23)18(13-31(21)15-40-41(36,37)38)22(33)25(35)30-10-8-29(9-11-30)24(34)17-6-4-3-5-7-17/h3-7,12-14H,8-11,15H2,1-2H3,(H2,36,37,38)
comment: Fostemsavir is a phosphonooxymethyl prodrug of temsavir (BMS-626529) <Reference id=39850/><Reference id=39853/>. It is classified as an attachment inhibitor <Reference id=39852/>. Temsavir binds to HIV envelope glycoprotein 120 (gp120) and thereby blocks viral attachment to the host CD4 molecule on T-lymphocytes. Naturally ocurring HIV-1 gp120 polymorphisms that could impart resistance to fostemsavir are uncommon <Reference id=39851/>.
iupac name: [3-[2-(4-benzoylpiperazin-1-yl)-2-oxoacetyl]-4-methoxy-7-(3-methyl-1,2,4-triazol-1-yl)pyrrolo[2,3-c]pyridin-1-yl]methyl dihydrogen phosphate
xref: CHEMBL3301594
synonym: BMS-663068
synonym: BMS663068
synonym: Rukobia®
synonym: GSK3684934
synonym: GSK-3684934
synonym: compound 35 [PMID: 29271653]
approved: t
ligand name: fostemsavir
type: SyntheticOrganicLigand

HTL22562
in ch i key: LIPVCPUZWNTQHV-SAIUNTKASA-N
in ch i: InChI=1S/C40H49N11O5/c1-26-21-28(22-29-25-44-48-34(26)29)24-32(46-38(54)51-15-8-40(9-16-51)31-3-2-10-43-35(31)47-39(55)56-40)36(52)45-33(23-27-4-11-41-12-5-27)37(53)50-19-17-49(18-20-50)30-6-13-42-14-7-30/h2-3,6-7,10,13-14,21-22,25,27,32-33,41H,4-5,8-9,11-12,15-20,23-24H2,1H3,(H,44,48)(H,45,52)(H,46,54)(H,43,47,55)/t32-,33+/m1/s1
comment: HTL22562 is a calcitonin gene-related peptide (CGRP) receptor antagonist <Reference id=39875/>. It was designed for the acute treatment of migraine. The X-ray crystal structure of HTL22562 bound to a CGRP receptor ectodomain heterodimer has been submitted to the RCSB Protein Data Bank (accession ID 6ZHO).
synonym: compound 8 [PMID: 32558564]
synonym: HTL-22562
approved: f
ligand name: HTL22562
type: SyntheticOrganicLigand

compound 27 [PMID: 32551645]
canonical SMILES: CCP(=O)(c1ccc2c(c1)nc(o2)c1ccc(cc1)F)OC
isomeric SMILES: CCP(=O)(c1ccc2c(c1)nc(o2)c1ccc(cc1)F)OC
in ch i key: MNCZMYLRBLYUPR-UHFFFAOYSA-N
in ch i: InChI=1S/C16H15FNO3P/c1-3-22(19,20-2)13-8-9-15-14(10-13)18-16(21-15)11-4-6-12(17)7-5-11/h4-10H,3H2,1-2H3
comment: Compound 27 was designed to offer improved clinical potential as a utrophin modulator than either <Ligand id=11110/> (failed at Phase 2) or <Ligand id=11111/> (terminated at preclinical) <Reference id=39874/>. This entry shows the compound without specified stereochemistry, to represent the racemic mixture. (+)-27 is slightly more active than (-)-27 or the racemate in vitro. Clinical rationale: Up-regulation of utrophin (UTRN; P46939) as being investigated as a disease-modifying approach for Duchenne muscular dystrophy (DMD). In the mdx mouse DMD model, increased levels of utrophin effectively acts as a substitute for the dystrophin (DMD; P11532) that is missing in DMD <Reference id=39870/>.
iupac name: methyl ethyl({2-[3-(trifluoromethyl)phenyl]-1,3-benzoxazol-5-yl})phosphinate
approved: f
ligand name: compound 27 [PMID: 32551645]
type: SyntheticOrganicLigand

SMT022357
in ch i key: GIJPBJLOHMBSSM-UHFFFAOYSA-N
in ch i: InChI=1S/C17H15F3NO3P/c1-3-25(22,23-2)13-7-8-15-14(10-13)21-16(24-15)11-5-4-6-12(9-11)17(18,19)20/h4-10H,3H2,1-2H3
comment: SMT022357 is a second-generation, oral utrophin modulator. It was developed from the same chemical series as clinically evaluated <Ligand id=11110/>, but with a new chemotype <Reference id=39873/>. SMT022357 has improved physicochemical and ADME properties compared to ezutromid, and has demonstrated efficacy in dystrophin-deficient mdx mice <Reference id=39872/><Reference id=39873/>. The molecular target of SMT022357 has not been reported, but may be the aryl hydrocarbon receptor, in common with ezutromid. Clinical rationale: Up-regulation of utrophin (UTRN; P46939) as being investigated as a disease-modifying approach for Duchenne muscular dystrophy (DMD). In the mdx mouse DMD model, increased levels of utrophin effectively acts as a substitute for the dystrophin (DMD; P11532) that is missing in DMD <Reference id=39870/>.
synonym: compound 4 [Babbs et al., 2020]
synonym: (±)-4
synonym: (±)-SMT022357
approved: f
ligand name: SMT022357
type: SyntheticOrganicLigand

ezutromid
in ch i key: KSGCNXAZROJSNW-UHFFFAOYSA-N
in ch i: InChI=1S/C19H15NO3S/c1-2-24(21,22)16-9-10-18-17(12-16)20-19(23-18)15-8-7-13-5-3-4-6-14(13)11-15/h3-12H,2H2,1H3
comment: Ezutromid (SMT C1100) is a clinical stage compound that was developed for its ability to increase expression of utrophin (UTRN; P46939), as a substitute for missing the dystrophin (DMD; P11532) in Duchenne muscular dystrophy (DMD) patients <Reference id=39870/>. It is orally active. The aryl hydrocarbon receptor (AhR) has been reported as a molecular target for ezutromid, with ezutromid behaving as an AhR antagonist <Reference id=39871/>. Ezutromid and other AhR antagonists up-regulate utrophin, adding to the proposition that this pathway offers disease-modifying potential for DMD.
iupac name: 5-ethylsulfonyl-2-naphthalen-2-yl-1,3-benzoxazole
xref: CHEMBL1773683
synonym: SMTC 1100
synonym: SMTC1100
synonym: 5-ethylsulfonyl-NBO
synonym: SMT C1100
approved: f
ligand name: ezutromid
type: SyntheticOrganicLigand

TCMDC-135051
in ch i key: LVVFYPXMXIDWRP-UHFFFAOYSA-N
in ch i: InChI=1S/C29H33N3O3/c1-6-32(7-2)17-20-9-8-10-23(27(20)35-5)26-16-25-21(13-14-30-28(25)31-26)19-11-12-22(29(33)34)24(15-19)18(3)4/h8-16,18H,6-7,17H2,1-5H3,(H,30,31)(H,33,34)
comment: TCMDC-135051 is a probe molecule identified as a selective inhibitor of P. falciparum cyclin-dependent-like kinase CLK3 (PfCLK3) and is being developed in a hit-to-lead programme <Reference id=39784/><Reference id=41130/>. The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
iupac name: 4-[2-[3-(diethylaminomethyl)-2-methoxyphenyl]-1H-pyrrolo[2,3-b]pyridin-4-yl]-2-propan-2-ylbenzoic acid
xref: CHEMBL531865
approved: f
ligand name: TCMDC-135051
type: SyntheticOrganicLigand

PBT2
canonical SMILES: CN(Cc1ccc2c(n1)c(O)c(cc2Cl)Cl)C
isomeric SMILES: CN(Cc1ccc2c(n1)c(O)c(cc2Cl)Cl)C
in ch i key: YZPOQCQXOSEMAZ-UHFFFAOYSA-N
in ch i: InChI=1S/C12H12Cl2N2O/c1-16(2)6-7-3-4-8-9(13)5-10(14)12(17)11(8)15-7/h3-5,17H,6H2,1-2H3
comment: PBT2 is an orally administered, safe-in-humans zinc ionophore. Chemically it is an 8-hydroxyquinoline analogue. PBT2 has been classified as a metal-protein attenuating compound (MPAC), and is designed to interfere with zinc ion interactions with proteins. Antibacterial activity: Whilst not active alone, PBT2 + zinc + antibacterial 'X' acts synergistically to overcome acquired bacterial-resistance to antibacterial 'X' (which can include clinically used antibacterials). This strategy produces activity against antibacterial-resistant Gram-positive pathogens <Reference id=39864/>. SARS-CoV-2: Based on evidence from previous studies in MERS-CoV and SARS-CoV-1, zinc modulation (e.g. by PBT2 or <Ligand id=7168/> <Reference id=39867/>) has been proposed as a potential mechanism for the prophylaxis/treatment of COVID-19. Altering zinc ion levels is predicted to affect activity of host and/or viral zinc-containing metalloenzymes.
iupac name: 5,7-dichloro-2-[(dimethylamino)methyl]quinolin-8-ol
xref: CHEMBL3634131
synonym: PBT-1033
synonym: PBT1033
synonym: PBT-2
approved: f
ligand name: PBT2
type: SyntheticOrganicLigand

TG-0203770
in ch i key: GENYQFMDDNZIRG-UCWBBBRQSA-N
in ch i: InChI=1S/C33H52N4O8/c1-8-43-27(38)15-14-25(19-24-16-17-34-29(24)39)35-30(40)26(18-21(2)3)36-31(41)28(22(4)45-33(5,6)7)37-32(42)44-20-23-12-10-9-11-13-23/h9-13,21-22,24-26,28H,8,14-20H2,1-7H3,(H,34,39)(H,35,40)(H,36,41)(H,37,42)/t22-,24+,25-,26+,28+/m1/s1
comment: TG-0203770 has been reported in complex with the 3CL protease (Mpro) of SARS-CoV-2 and the chemical structure was obtained from RCSB Protein Database entry 7C8R. This interaction remains unpublished so there is not yet any inhibition data that can be curated into the Guide to PHARMACOLOGY. Previous data for other coronaviruses was reported in 2009 <Reference id=40476/>. TG-0203770 is an aza-peptide peptidomimetic and its IUPAC condensed nomenclature is Cbz-Thr(tBu)-Leu-Unk.
approved: f
ligand name: TG-0203770
type: SyntheticOrganicLigand

example 2 [WO2005113580A1]
in ch i key: FDQSUXUTXIGUIA-PRIDNEQBSA-N
in ch i: InChI=1S/C24H34N4O6/c1-13(2)9-18(23(32)27-17(20(30)12-29)10-14-7-8-25-22(14)31)28-24(33)19-11-15-16(26-19)5-4-6-21(15)34-3/h4-6,11,13-14,17-18,20,26,29-30H,7-10,12H2,1-3H3,(H,25,31)(H,27,32)(H,28,33)/t14-,17-,18-,20+/m0/s1
comment: Example 2 is a covalent inhibitor of the 3CL protease (Mpro) of the SARS-CoV-1 coronavirus <Reference id=39863/>. The compound has been shown in complex with SARS-CoV-2 Mpro (see RCSB Protein Database entry 6XHM).
approved: f
ligand name: example 2 [WO2005113580A1]
type: SyntheticOrganicLigand

LB-100
in ch i key: JUQMLSGOTNKJKI-IZUQBHJASA-N
in ch i: InChI=1S/C13H20N2O4/c1-14-4-6-15(7-5-14)12(16)10-8-2-3-9(19-8)11(10)13(17)18/h8-11H,2-7H2,1H3,(H,17,18)/t8-,9+,10?,11?/m0/s1
comment: LB-100 is a small molecule inhibitor of protein phosphatase 2A (PP2A) <Reference id=39860/>. PP2A is a pivotal cellular switch that controls important events that impinge on cellular survival and death, such as cell cycle, apoptosis, and autophagy. PP2A acts on kinase substrates in a number of critical signal transduction pathways (including MAPK, Wnt, PI3K, NF&kappB, PKC, and Ca2+/calmodulin-dependent signalling pathways). PP2A is a validated oncology target. Studies have shown that LB-100 has anti-tumour activity <Reference id=39861/> and can sensitise pancreatic cancer to chemotherapy <Reference id=39862/> and radiotherapy <Reference id=39860/>.
iupac name: (1R,4S)-3-(4-methylpiperazine-1-carbonyl)-7-oxabicyclo[2.2.1]heptane-2-carboxylic acid
xref: CHEMBL4297300
synonym: LB100
approved: f
ligand name: LB-100
type: SyntheticOrganicLigand

SL-176
in ch i key: WYYKYBVYKSTHEV-RSBOXOOMSA-N
in ch i: InChI=1S/C24H48O4Si2/c1-10-30(11-2,12-3)28-21-15-13-14-20-19(21)16-18(17-24(20,7)22(25)26)27-29(8,9)23(4,5)6/h18-21H,10-17H2,1-9H3,(H,25,26)/t18-,19-,20+,21+,24+/m0/s1
comment: SL-176 is a small molecule inhibitor of the metal-dependent Ser/Thr phosphatase PPM1D <Reference id=39859/>. It decreases PPM1D enzyme activity in vitro. Exposure of breast cancer cells overexpressing PPM1D induces G2/M arrest and apoptosis. SL-176's antiproliferative effect is independent of TP53 status.
iupac name: (1R,3S,4aS,5R,8aR)-3-[tert-butyl(dimethyl)silyl]oxy-1-methyl-5-triethylsilyloxy-3,4,4a,5,6,7,8,8a-octahydro-2H-naphthalene-1-carboxylic acid
synonym: SL176
approved: f
ligand name: SL-176
type: SyntheticOrganicLigand

GSK2830371
in ch i key: IVDUVEGCMXCMSO-FQEVSTJZSA-N
comment: GSK2830371 is an orally active, small-molecule inhibitor of metal-dependent Ser/Thr phosphatase PPM1D <Reference id=39858/>. Inhibition of PPM1D increases phosphorylation (inhibits dephosphorylation) of PPM1D substrates. GSK2830371 binds at an allosteric position close to PPM1D's catalytic site. Referred to as the 'flap' subdomain, this region is unique to PPM1D compared to other members of the PPM phosphatase family, and this confers PPM1D selectivity. GSK2830371 appears to be effective only in cell lines overexpressing PPM1D and with wild-type TP53 (HGNC:11998). Cell lines with mutant TP53 seem to be resistant to GSK2830371.
iupac name: 5-[[(5-chloro-2-methylpyridin-3-yl)amino]methyl]-N-[(2S)-3-cyclopentyl-1-(cyclopropylamino)-1-oxopropan-2-yl]thiophene-2-carboxamide
xref: CHEMBL3613749
synonym: GSK-2830371
synonym: compound 8 [PMID: 24390428]
approved: f
ligand name: GSK2830371
type: SyntheticOrganicLigand

emetine
in ch i key: AUVVAXYIELKVAI-CKBKHPSWSA-N
in ch i: InChI=1S/C29H40N2O4/c1-6-18-17-31-10-8-20-14-27(33-3)29(35-5)16-23(20)25(31)12-21(18)11-24-22-15-28(34-4)26(32-2)13-19(22)7-9-30-24/h13-16,18,21,24-25,30H,6-12,17H2,1-5H3/t18-,21-,24+,25-/m0/s1
comment: Emetine is a plant metabolite from ipecac root.
iupac name: (2S,3R,11bS)-2-[[(1R)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolin-1-yl]methyl]-3-ethyl-9,10-dimethoxy-2,3,4,6,7,11b-hexahydro-1H-benzo[a]quinolizine
xref: CHEMBL50588
approved: f
ligand name: emetine
type: NaturalProductLigand

A-1331852
in ch i key: QCQQONWEDCOTBV-UHFFFAOYSA-N
in ch i: InChI=1S/C38H38N6O3S/c1-22-29(19-39-44(22)21-38-16-23-13-24(17-38)15-25(14-23)18-38)27-9-10-33(41-34(27)36(46)47)43-12-11-26-5-4-6-28(30(26)20-43)35(45)42-37-40-31-7-2-3-8-32(31)48-37/h2-10,19,23-25H,11-18,20-21H2,1H3,(H,46,47)(H,40,42,45)
comment: Highly potent and selective Bcl-xL (Bcl-2-like 1) inhibitor.
iupac name: 3-[1-(1-adamantylmethyl)-5-methylpyrazol-4-yl]-6-[8-(1,3-benzothiazol-2-ylcarbamoyl)-3,4-dihydro-1H-isoquinolin-2-yl]pyridine-2-carboxylic acid
synonym: A1331852
synonym: A 1331852
approved: f
ligand name: A-1331852
type: SyntheticOrganicLigand

cedazuridine
in ch i key: VUDZSIYXZUYWSC-DBRKOABJSA-N
in ch i: InChI=1S/C9H14F2N2O5/c10-9(11)6(16)4(3-14)18-7(9)13-2-1-5(15)12-8(13)17/h4-7,14-16H,1-3H2,(H,12,17)/t4-,5-,6-,7-/m1/s1
comment: Cedazuridine is a tetrahydrouridine-derived, orally available synthetic nucleoside analogue that was developed by Astex Pharmaceuticals. It inhibits cytidine deaminase (CDA) and was designed to be used as a pharmacoenhancer of drugs that are subject to CDA-mediated breakdown, for example the cytidine analogue antineoplastic hypomethylating agent <Ligand id=6805/>. This mechanism permits oral delivery of decitabine (by inhibiting decitabine degradation in the gut and liver). It also allows lower doses of decitabine to be used, which improves tolerability to this cancer drug, whose administration is associated with GI-toxicity.
iupac name: (4R)-1-[(2R,4R,5R)-3,3-difluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-hydroxy-1,3-diazinan-2-one
xref: CHEMBL3237547
synonym: (4R)-2'-deoxy-2',2'-difluoro-3,4,5,6-tetrahydrouridine
synonym: ASTX727 (cedazuridine + decitabine)
synonym: compound 7a [PMID: 24520856]
approved: t
ligand name: cedazuridine
type: SyntheticOrganicLigand

compound 3m [PMID: 32603117]
in ch i key: BOOYHBPHFVNWNH-OAHLLOKOSA-N
in ch i: InChI=1S/C24H25ClFN5O/c1-15(17-7-9-18(25)10-8-17)28-23-29-21-20(13-27-31(21)24(2,3)4)22(32)30(23)14-16-5-11-19(26)12-6-16/h5-13,15H,14H2,1-4H3,(H,28,29)/t15-/m1/s1
comment: Compound 3m is reported as a PDE1 inhibitor <Reference id=39845/>. It is proposed for potential to treat idiopathic pulmonary fibrosis.
iupac name: (R)-1-(tert-Butyl)-6-((1-(4-chlorophenyl)ethyl)amino)-5-(4-fluorobenzyl)-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one
approved: f
ligand name: compound 3m [PMID: 32603117]
type: SyntheticOrganicLigand

IRL752
canonical SMILES: CO[C@]1(CNCC1)c1cccc(c1F)F
isomeric SMILES: CO[C@]1(CNCC1)c1cccc(c1F)F
in ch i key: LJNFYMMXCXGFCP-LLVKDONJSA-N
in ch i: InChI=1S/C11H13F2NO/c1-15-11(5-6-14-7-11)8-3-2-4-9(12)10(8)13/h2-4,14H,5-7H2,1H3/t11-/m1/s1
comment: Effector studies show that IRL752 acts an antagonist at 5-hydroxytryptamine-7 receptor (serotonin-7, 5-HT7R) and cortical alpha receptor (alpha-2CR) <Reference id=39838/>. Being developed for the treatment of impaired balance (postural dysfunction) and falls in Parkinson's disease <Reference id=39838/>.
iupac name: (3S)-3-(2,3-difluorophenyl)-3-methoxypyrrolidine
synonym: IRL-752
synonym: IRL 752
approved: f
ligand name: IRL752
type: SyntheticOrganicLigand

MAPK13-IN-1
in ch i key: MHSLDASSAFCCDO-UHFFFAOYSA-N
in ch i: InChI=1S/C20H23N5O2/c1-20(2,3)17-13-18(25(4)24-17)23-19(26)22-14-5-7-15(8-6-14)27-16-9-11-21-12-10-16/h5-13H,1-4H3,(H2,22,23,26)
comment: This compound was claimed as a MAPK13 (p38δ) inhibitor in patent WO2014015056A2 <Reference id=39821/>. MAPK13-IN-1 was proposed for mucous-reducing activity with application in respiratory diseases like asthma and COPD. It was designed to act by reducing MAPK13 signalling-induced mucous production by airway epithelial cells in response to activation by the pro-inflammatory cytokine, IL-13 <Reference id=19764/>. MAPK13-IN-1 binds to MAPK13 in DFG-out mode and exhibits slow dissociation kinetics.
iupac name: 1-(5-tert-butyl-2-methylpyrazol-3-yl)-3-(4-pyridin-4-yloxyphenyl)urea
xref: CHEMBL472620
synonym: compound 61 [WO2014015056A2]
approved: f
ligand name: MAPK13-IN-1
type: SyntheticOrganicLigand

ARRY-371797
in ch i key: IFGWYHGYNVGVRB-UHFFFAOYSA-N
in ch i: InChI=1S/C22H26F2N4O2/c1-14(2)13-28-19-11-17(22(29)25-7-8-27(3)4)21(9-15(19)12-26-28)30-20-6-5-16(23)10-18(20)24/h5-6,9-12,14H,7-8,13H2,1-4H3,(H,25,29)
comment: ARRY-371797 is a clinical stage, oral, p38α (MAPK14)-selective kinase inhibitor that was originally developed by Array BioPharma (a Pfizer owned company since mid-2019) for anti-inflammatory and analgesic potential <Reference id=25972/>. However, development for chronic inflammatory diseases has since been terminated. No results from completed analgesia trials have been published. Subsequent repositioning has seen the focus transfer to ARRY-371797 for LMNA-related dilated cardiomyopathy. p38α signalling is hyperactivated in mice with cardiomyopathy caused by lamin A/C gene (LMNA) mutation <Reference id=39820/> and p38α activation is observed in the hearts from human subjects with LMNA-related dilated cardiomyopathy, thus ARRY-371797 has been advanced as a therapeutic option for this indication.
iupac name: -(2,4-difluorophenoxy)-N-[2-(dimethylamino)ethyl]-1-(2-methylpropyl)indazole-6-carboxamide
xref: CHEMBL1088750
synonym: ARRY-797
synonym: ARRY797
synonym: ARRY371797
synonym: compound 7 [PMID: 19950901]
approved: f
ligand name: ARRY-371797
type: SyntheticOrganicLigand

cannabigerol
canonical SMILES: CCCCCc1cc(O)c(c(c1)O)C/C=C(/CCC=C(C)C)/C
isomeric SMILES: CCCCCc1cc(O)c(c(c1)O)C/C=C(/CCC=C(C)C)/C
in ch i key: QXACEHWTBCFNSA-SFQUDFHCSA-N
in ch i: InChI=1S/C21H32O2/c1-5-6-7-11-18-14-20(22)19(21(23)15-18)13-12-17(4)10-8-9-16(2)3/h9,12,14-15,22-23H,5-8,10-11,13H2,1-4H3/b17-12+
comment: Cannabigerol (CBG) is a phytocannabinoid that is a biosynthetic presursor for the synthesis of other cannabinoids. It is a minor constituent of herbal cannabis.
xref: CHEMBL497318
synonym: CBG
approved: f
ligand name: cannabigerol
type: NaturalProductLigand

cannabichromene
canonical SMILES: CCCCCc1cc2OC(C)(CCC=C(C)C)C=Cc2c(c1)O
isomeric SMILES: CCCCCc1cc2OC(C)(CCC=C(C)C)C=Cc2c(c1)O
in ch i key: UVOLYTDXHDXWJU-UHFFFAOYSA-N
in ch i: InChI=1S/C21H30O2/c1-5-6-7-10-17-14-19(22)18-11-13-21(4,23-20(18)15-17)12-8-9-16(2)3/h9,11,13-15,22H,5-8,10,12H2,1-4H3
comment: Cannabichromene (CBC) is a phytocannabinoid.
iupac name: 2-methyl-2-(4-methylpent-3-enyl)-7-pentylchromen-5-ol
xref: CHEMBL422704
synonym: CBC
synonym: (+/-)-Cannabichromene
synonym: cannabichrome
approved: f
ligand name: cannabichromene
type: NaturalProductLigand

cannabidivarin
in ch i key: REOZWEGFPHTFEI-CVEARBPZSA-N
in ch i: InChI=1S/C19H26O2/c1-5-6-14-10-17(20)19(18(21)11-14)16-9-13(4)7-8-15(16)12(2)3/h9-11,15-16,20-21H,2,5-8H2,1,3-4H3/t15-,16+/m1/s1
comment: Cannabidivarin is a non-psychoactive phytocannabinoid found in plants of the Cannabis species.
iupac name: 2-[(1S,6S)-3-methyl-6-prop-1-en-2-ylcyclohex-2-en-1-yl]-5-propylbenzene-1,3-diol
synonym: CBDV
synonym: GWP42006
approved: f
ligand name: cannabidivarin
type: NaturalProductLigand

Δ9-Tetrahydrocannabinolic acid
in ch i key: UCONUSSAWGCZMV-HZPDHXFCSA-N
in ch i: InChI=1S/C22H30O4/c1-5-6-7-8-14-12-17-19(20(23)18(14)21(24)25)15-11-13(2)9-10-16(15)22(3,4)26-17/h11-12,15-16,23H,5-10H2,1-4H3,(H,24,25)/t15-,16-/m1/s1
comment: Δ9-tetrahydrocannabinolic acid is a phytocannabinoid. It is a precursor used in the biosysnthesis of Δ9-tetrahydrocannabinol (Δ9-THC), the principal psychoactive component from the cannabis plant Cannabis sativa.
iupac name: (6aR,10aR)-1-hydroxy-6,6,9-trimethyl-3-pentyl-6a,7,8,10a-tetrahydrobenzo[c]chromene-2-carboxylic acid
xref: CHEMBL465718
synonym: Delta(9)-tetrahydrocannabinolic acid
synonym: Δ9-tetrahydrocannabinolic acid
synonym: 9-Carboxy-THC
synonym: THCA
approved: f
ligand name: Δ9-Tetrahydrocannabinolic acid
type: NaturalProductLigand

nelfinavir
in ch i key: QAGYKUNXZHXKMR-HKWSIXNMSA-N
in ch i: InChI=1S/C32H45N3O4S/c1-21-25(15-10-16-28(21)36)30(38)33-26(20-40-24-13-6-5-7-14-24)29(37)19-35-18-23-12-9-8-11-22(23)17-27(35)31(39)34-32(2,3)4/h5-7,10,13-16,22-23,26-27,29,36-37H,8-9,11-12,17-20H2,1-4H3,(H,33,38)(H,34,39)/t22-,23+,26-,27-,29+/m0/s1
comment: Nelfinavir is an oral antiretroviral drug. It inhibits human immunodeficiency virus (HIV) protease.
iupac name: (3S,4aS,8aS)-N-tert-butyl-2-[(2R,3R)-2-hydroxy-3-[(3-hydroxy-2-methylbenzoyl)amino]-4-phenylsulfanylbutyl]-3,4,4a,5,6,7,8,8a-octahydro-1H-isoquinoline-3-carboxamide
xref: CHEMBL1205
synonym: AG-1343
synonym: AG1343
synonym: Viracept®
approved: t
ligand name: nelfinavir
type: SyntheticOrganicLigand

umifenovir
in ch i key: KCFYEAOKVJSACF-UHFFFAOYSA-N
comment: Umifenovir is an indole-based antiviral drug. It is a viral entry inhibitor <Reference id=39811/> and also acts to modulate the host immune response (induces interferon-production, stimulates macrophages phagocytosis).
iupac name: ethyl 6-bromo-4-[(dimethylamino)methyl]-5-hydroxy-1-methyl-2-(phenylsulfanylmethyl)indole-3-carboxylate
xref: CHEMBL1214598
synonym: Arbidol®
synonym: AR-1I9514
approved: f
ligand name: umifenovir
type: SyntheticOrganicLigand

salinomycin
in ch i key: KQXDHUJYNAXLNZ-XQSDOZFQSA-N
in ch i: InChI=1S/C42H70O11/c1-11-29(38(46)47)31-15-14-23(4)36(50-31)27(8)34(44)26(7)35(45)30(12-2)37-24(5)22-25(6)41(51-37)19-16-32(43)42(53-41)21-20-39(10,52-42)33-17-18-40(48,13-3)28(9)49-33/h16,19,23-34,36-37,43-44,48H,11-15,17-18,20-22H2,1-10H3,(H,46,47)/t23-,24-,25+,26-,27-,28-,29+,30-,31+,32+,33+,34+,36+,37-,39-,40+,41-,42-/m0/s1
comment: Salinomycin is an ionophore antibacterial, from which <Ligand id=10835/> was derived. It is primarily used in veterinary practice. Salinomycin has potent antimicrobial activity against Gram-positive bacteria and is inactive against Gram-negative bacteria <Reference id=39807/>.
iupac name: (2R)-2-[(2R,5S,6R)-6-[(2S,3S,4S,6R)-6-[(3S,5S,7R,9S,10S,12R,15R)-3-[(2R,5R,6S)-5-ethyl-5-hydroxy-6-methyloxan-2-yl]-15-hydroxy-3,10,12-trimethyl-4,6,8-trioxadispiro[4.1.57.35]pentadec-13-en-9-yl]-3-hydroxy-4-methyl-5-oxooctan-2-yl]-5-methyloxan-2-yl]butanoic acid
xref: CHEMBL1208572
synonym: Procoxacin®
synonym: Coxistac®
approved: f
ligand name: salinomycin
type: SyntheticOrganicLigand

phenacemide
canonical SMILES: OC(=NC(=N)O)Cc1ccccc1
isomeric SMILES: OC(=NC(=N)O)Cc1ccccc1
in ch i key: XPFRXWCVYUEORT-UHFFFAOYSA-N
in ch i: InChI=1S/C9H10N2O2/c10-9(13)11-8(12)6-7-4-2-1-3-5-7/h1-5H,6H2,(H3,10,11,12,13)
comment: Phenacemide is a ureide (acetylurea) anticonvulsant. It is a congener and ring-opened analogue of the hydantoin <Ligand id=2624/>, and is structurally related to the barbiturate family of drugs and other hydantoins. Use of phenacemide was widely discontinued due to toxic side-effects.
iupac name: 1-[(C-hydroxycarbonimidoyl)imino]-2-phenylethan-1-ol
xref: CHEMBL918
synonym: Phenurone®
approved: t
ligand name: phenacemide
type: SyntheticOrganicLigand

HTH-02-006
in ch i key: KQMWYEJQANQTDM-UHFFFAOYSA-N
in ch i: InChI=1S/C25H29IN6O3/c1-4-23(33)28-17-6-5-7-19(14-17)35-24-20(26)16-27-25(30-24)29-21-9-8-18(15-22(21)34-3)32-12-10-31(2)11-13-32/h5-9,14-16H,4,10-13H2,1-3H3,(H,28,33)(H,27,29,30)
comment: HTH-02-006 is a reversible small-molecule inhibitor of the Hippo pathway kinase, NUAK2 <Reference id=39792/>. It can be used as a tool compound to investigate the role of NUAK2 in cancer and other Hippo pathway-associated biological processes <Reference id=39793/><Reference id=39794/>. HTH-02-006 is a derivative of the prototype NUAK inhibitor <Ligand id=8047/>. It is active in vivo.
iupac name: N-(3-((5-iodo-2-((2-methoxy-4-(4-methylpiperazin-1-yl)phenyl)amino)pyrimidin-4-yl)oxy)phenyl)propionamide
approved: f
ligand name: HTH-02-006
type: SyntheticOrganicLigand

LIH383
in ch i key: SGGIVBFIASEYOE-LBBUGJAGSA-N
in ch i: InChI=1S/C45H71N15O9S/c1-70-23-19-33(59-42(67)35(25-29-14-6-3-7-15-29)56-37(62)27-54-36(61)26-55-38(63)30(47)24-28-12-4-2-5-13-28)41(66)58-31(17-10-21-52-44(48)49)39(64)57-32(18-11-22-53-45(50)51)40(65)60-34(43(68)69)16-8-9-20-46/h2-7,12-15,30-35H,8-11,16-27,46-47H2,1H3,(H,54,61)(H,55,63)(H,56,62)(H,57,64)(H,58,66)(H,59,67)(H,60,65)(H,68,69)(H4,48,49,52)(H4,50,51,53)/t30-,31-,32-,33-,34-,35-/m0/s1
comment: LIH383 is a highly selective subnanomolar agonist of ACKR3/CXCR7 <Reference id=39763/>.
approved: f
ligand name: LIH383
type: PeptideLigand

compound 36 [PMID: 32429662]
in ch i key: PBXCPFNNNZUANE-UHFFFAOYSA-N
in ch i: InChI=1S/C23H21ClN2O2/c24-20-6-3-7-21(15-20)25-22(27)17-10-12-26(13-11-17)23(28)19-9-8-16-4-1-2-5-18(16)14-19/h1-9,14-15,17H,10-13H2,(H,25,27)
comment: Compound 36 is reported as a first-in-class reversible inhibitor of monoacylglycerol lipase (MAGL) <Reference id=39791/>.
iupac name: 1-(2-Naphthoyl)-N-(3-chlorophenyl)piperidine-4-carboxamide
approved: f
ligand name: compound 36 [PMID: 32429662]
type: SyntheticOrganicLigand

LASSBio-1524
canonical SMILES: O=C(c1ccc2c(c1)cccc2)N/N=C/c1ccc(cc1)[N+](=O)[O-]
isomeric SMILES: O=C(c1ccc2c(c1)cccc2)N/N=C/c1ccc(cc1)[N+](=O)[O-]
in ch i key: RUQCGNRXDVIDAJ-XDHOZWIPSA-N
in ch i: InChI=1S/C18H13N3O3/c22-18(16-8-7-14-3-1-2-4-15(14)11-16)20-19-12-13-5-9-17(10-6-13)21(23)24/h1-12H,(H,20,22)/b19-12+
comment: LASSBio-1524 is an inhibitor of the IKK-β (kappa β kinase inhibitor) enzyme, which participates in the activation of the nuclear factor κB (NF-κB) canonical pathway.
xref: CHEMBL1760505
approved: f
ligand name: LASSBio-1524
type: SyntheticOrganicLigand

OM-1700
in ch i key: ZBRBBDJXHBEGHX-QAQDUYKDSA-N
in ch i: InChI=1S/C25H23FN6O2/c1-2-34-18-10-11-20(28-15-18)24-31-30-23(32(24)22-9-4-3-7-19(22)26)16-13-17(14-16)29-25(33)21-8-5-6-12-27-21/h3-12,15-17H,2,13-14H2,1H3,(H,29,33)/t16-,17-
comment: OM-1700 (compound 13) is an orally bioavailable tankyrase inhibitor <Reference id=39790/>. It has a more favourable ADME profile than existing tankyrase inhibitors.
iupac name: 3-(trans-3-(5-(5-Ethoxypyridin-2-yl)-4-(2-fluorophenyl)-4H-1,2,4-triazol-3-yl)cyclobutyl)picolinamide
synonym: compound 13 [PMID: 32511917]
synonym: OM1700
approved: f
ligand name: OM-1700
type: SyntheticOrganicLigand

PSB-KD107
in ch i key: PUJKERUFRDZALE-UHFFFAOYSA-N
in ch i: InChI=1S/C20H22N6O2/c1-23-17-16(18(27)24(2)20(23)28)26-10-5-9-25(19(26)22-17)11-8-13-12-21-15-7-4-3-6-14(13)15/h3-4,6-7,12,21H,5,8-11H2,1-2H3
comment: PSB-KD107 is a first-in-class non-lipid-like agonist of the orphan G-protein-coupled receptor GPR18 <Reference id=39788/>. In a GPR18-dependent β-arrestin recruitment assay, PSB-KD107 is significantly more potent and efficacious than the natural cannabinoid agonist Δ9-tetrahydrocannabinol (THC). PSB-KD107 is selective for GPR18 over the cannabinoid-sensitive receptors CB1, CB2, and GPR55.
iupac name: 9-[2-(1H-indol-3-yl)ethyl]-1,3-dimethyl-7,8-dihydro-6H-purino[7,8-a]pyrimidine-2,4-dione
xref: CHEMBL239232
synonym: compound 5 [Schoeder et al., 2020]
synonym: compound 2Ak [PMID: 17827019]
approved: f
ligand name: PSB-KD107
type: SyntheticOrganicLigand

tatM2NX
in ch i key: UDMRTOJWVGSXRR-OMVNHVILSA-N
comment: TatM2NX is a cell permeable peptide-inhibitor (antagonist) of the transient receptor potential melastatin 2 (TRPM2) ion channel <Reference id=39782/>. The M2NX portion of the peptide targets the Nudix motif ADP ribose binding site at the C-terminal of the TRPM2 channel and the N terminus tat-human immunodeficiency virus (HIV) sequence YGRKKRRQRRR mediates cell permeability. TatM2NX can be used as a tool to study TRPM2's role in brain physiology and pathophysiology, and its clinical potential as a novel neuroprotective target for the treatment of neurological diseases.
synonym: tat-M2NX
approved: f
ligand name: tatM2NX
type: PeptideLigand

GRL-0617
in ch i key: UVERBUNNCOKGNZ-CQSZACIVSA-N
in ch i: InChI=1S/C20H20N2O/c1-13-10-11-16(21)12-19(13)20(23)22-14(2)17-9-5-7-15-6-3-4-8-18(15)17/h3-12,14H,21H2,1-2H3,(H,22,23)/t14-/m1/s1
comment: GRL-0617 is an inhibitor of SARS-CoV and SARS-CoV-2 papain-like proteases (PL-pro) <Reference id=39774/><Reference id=39773/>. It is selective for the viral proteases over human proteases. GRL-0617 blocks both PL-pro-mediated actions towards host biological processes and virus replication <Reference id=39772/>.
iupac name: 5-amino-2-methyl-N-[(1R)-1-naphthalen-1-ylethyl]benzamide
xref: CHEMBL549695
synonym: GRL0617
synonym: compound 25 [PMID: 19645480]
approved: f
ligand name: GRL-0617
type: SyntheticOrganicLigand

compound 13B [PMID: 32506913]
canonical SMILES: O[C@@H]1CC[C@H](CC1)NC(=O)CCCCCc1ccccc1
isomeric SMILES: O[C@@H]1CC[C@H](CC1)NC(=O)CCCCCc1ccccc1
in ch i key: SUKXKLNDBLNTSW-QAQDUYKDSA-N
in ch i: InChI=1S/C18H27NO2/c20-17-13-11-16(12-14-17)19-18(21)10-6-2-5-9-15-7-3-1-4-8-15/h1,3-4,7-8,16-17,20H,2,5-6,9-14H2,(H,19,21)/t16-,17-
comment: Compound 13B is a potent stereoselective mitofusin activator <Reference id=39766/>. It was developed as a potential lead compound for the mitochondrial disorder Charcot-Marie-tooth disease 2A, that is caused by mutation in the MFN2 gene. The activator enhances mitochondrial fusion and improves mitochondrial dynamics. It has a favourable ADME profile and in vivo target engagement is observed.
iupac name: N-(trans-4-Hydroxycyclohexyl)-6-phenylhexanamide
approved: f
ligand name: compound 13B [PMID: 32506913]
type: SyntheticOrganicLigand

AS3334034
in ch i key: WCPMUQAUSFXFJE-UHFFFAOYSA-N
in ch i: InChI=1S/C18H22N4O3S/c1-11-10-20-22-17(11)21-13-6-7-19-14-9-15(25-5)16(8-12(13)14)26(23,24)18(2,3)4/h6-10H,1-5H3,(H2,19,20,21,22)
comment: Receptor-interacting Protein Kinase 2 (RIP2) inhibitor. AS3334034 may be useful in the treatment of patients with chronic kidney disease.
iupac name: 7-methoxy-6-(2-methylpropane-2-sulfonyl)-N-(4-methyl-1H-pyrazol-3-yl)quinolin-4-amine
approved: f
ligand name: AS3334034
type: SyntheticOrganicLigand

AS408
canonical SMILES: Brc1ccc2c(c1)c(N)nc(n2)Nc1ccccc1
isomeric SMILES: Brc1ccc2c(c1)c(N)nc(n2)Nc1ccccc1
in ch i key: MPGNABXYXOGUGH-UHFFFAOYSA-N
in ch i: InChI=1S/C14H11BrN4/c15-9-6-7-12-11(8-9)13(16)19-14(18-12)17-10-4-2-1-3-5-10/h1-8H,(H3,16,17,18,19)
comment: Allosteric modulator of the β2-adrenergic receptor.
iupac name: 6-bromo-2-N-phenylquinazoline-2,4-diamine
approved: f
ligand name: AS408
type: SyntheticOrganicLigand

S‐Y048
in ch i key: XGNFPJZMWOIDAH-SFHVURJKSA-N
in ch i: InChI=1S/C27H31Cl2NO3/c1-18(15-26(32)33)14-25(31)27-22-17-21(29)12-13-23(22)30(2)24(27)11-6-4-3-5-8-19-9-7-10-20(28)16-19/h7,9-10,12-13,16-18H,3-6,8,11,14-15H2,1-2H3,(H,32,33)/t18-/m0/s1
comment: Potent OXE receptor antagonist. May be a useful anti‐inflammatory agent for the treatment of eosinophilic diseases such as asthma, allergic rhinitis, and atopic dermatitis.
iupac name: (3S)-5-[5-chloro-2-[6-(3-chlorophenyl)hexyl]-1-methylindol-3-yl]-3-methyl-5-oxopentanoic acid
synonym: S-Y048
approved: f
ligand name: S‐Y048
type: SyntheticOrganicLigand

SENS-111
canonical SMILES: CNC1CN(C1)c1cc(N)nc(n1)CC(C)C
isomeric SMILES: CNC1CN(C1)c1cc(N)nc(n1)CC(C)C
in ch i key: QRBVUFXEMHNIDB-UHFFFAOYSA-N
in ch i: InChI=1S/C12H21N5/c1-8(2)4-11-15-10(13)5-12(16-11)17-6-9(7-17)14-3/h5,8-9,14H,4,6-7H2,1-3H3,(H2,13,15,16)
comment: SENS-111 (Seliforant) is an orally available small molecule histamine type 4 receptor antagonist, displaying an inhibitory effect on vestibular neuron activity.
iupac name: 6-[3-(methylamino)azetidin-1-yl]-2-(2-methylpropyl)pyrimidin-4-amine
approved: f
ligand name: SENS-111
type: SyntheticOrganicLigand

compound 11b [PMID: 32321856]
in ch i key: HCRBVFBQANEDDM-DSKINZAPSA-N
in ch i: InChI=1S/C25H25FN4O4/c26-18-6-3-4-15(10-18)11-21(24(33)28-19(14-31)12-17-8-9-27-23(17)32)30-25(34)22-13-16-5-1-2-7-20(16)29-22/h1-7,10,13-14,17,19,21,29H,8-9,11-12H2,(H,27,32)(H,28,33)(H,30,34)/t17-,19+,21-/m0/s1
comment: Compound 11b is an inhibitor of SARS-CoV-2 main protease (Mpro) <Reference id=39756/>. It interacts with Cys145 of Mpro and it inhibits both protease activity and SARS-CoV-2 infectivity in vitro. Compound 11b was discovered in the same series as <Ligand id=11070/>.
approved: f
ligand name: compound 11b [PMID: 32321856]
type: SyntheticOrganicLigand

compound 11a [PMID: 32321856]
in ch i key: HPKJGHVHQWJOOT-ZJOUEHCJSA-N
in ch i: InChI=1S/C25H32N4O4/c30-15-19(13-18-10-11-26-23(18)31)27-24(32)21(12-16-6-2-1-3-7-16)29-25(33)22-14-17-8-4-5-9-20(17)28-22/h4-5,8-9,14-16,18-19,21,28H,1-3,6-7,10-13H2,(H,26,31)(H,27,32)(H,29,33)/t18-,19-,21-/m0/s1
comment: Compound 11a is an inhibitor of SARS-CoV-2 main protease (Mpro) <Reference id=39756/>. It interacts with Cys145 of Mpro and it inhibits both protease activity and SARS-CoV-2 infectivity in vitro. Given its low in vivo toxicity and favourable PK profile, 11a is considered to be a valuable lead candidate. Based on commentary in a review by Zhao et al. (2022) <Reference id=43629/>, compound 11a appears to be the Mpro inhibitor that is being tested in clinical trials as FB2001 (and which is also known as DC402234).
iupac name: N-[(2S)-3-cyclohexyl-1-oxo-1-[[(2S)-1-oxo-3-[(3S)-2-oxopyrrolidin-3-yl]propan-2-yl]amino]propan-2-yl]-1H-indole-2-carboxamide
synonym: FB2001
synonym: FB-2001
synonym: DC402234
synonym: DC-402234
approved: f
ligand name: compound 11a [PMID: 32321856]
type: SyntheticOrganicLigand

hexachlorophene
in ch i key: ACGUYXCXAPNIKK-UHFFFAOYSA-N
in ch i: InChI=1S/C13H6Cl6O2/c14-6-2-8(16)12(20)4(10(6)18)1-5-11(19)7(15)3-9(17)13(5)21/h2-3,20-21H,1H2
comment: Hexachlorophene is used as a topical anti-infective, anti-bacterial agent, and as a soil fungicide, plant bactericide. It exhibits bacteriostatic action against Gram-positive organisms, but is much less effective against Gram-negative organisms. Reported to inhibit N-Acyl-phosphatidylethanolamine phospholipase D (NAPE-PLD) activity <Reference id=39755/>.
iupac name: 3,4,6-trichloro-2-[(2,3,5-trichloro-6-hydroxyphenyl)methyl]phenol
xref: CHEMBL496
synonym: Inh 1 [PMID: 32284327]
synonym: Nabac®
approved: t
ligand name: hexachlorophene
type: SyntheticOrganicLigand

ADG-207
in ch i key: SCPZMCCNFFWXMO-UHFFFAOYSA-N
in ch i: InChI=1S/C27H26N4OS2/c32-26(31-27-13-16-9-17(14-27)11-18(10-16)15-27)28-19-5-6-20-21(12-19)30-25(23-4-2-8-34-23)24(29-20)22-3-1-7-33-22/h1-8,12,16-18H,9-11,13-15H2,(H2,28,31,32)
comment: ADG-207 is an acetate-dependent acetyl-CoA synthetase 2 (ACSS2) inhibitor <Reference id=39750/>.
iupac name: 1-(1-adamantyl)-3-(2,3-dithiophen-2-ylquinoxalin-6-yl)urea
approved: f
ligand name: ADG-207
type: SyntheticOrganicLigand

example 265 [WO2019097515A1]
in ch i key: FEYNFHSRETUBEM-UHFFFAOYSA-N
in ch i: InChI=1S/C20H19F2N3O3/c1-12-17(18(26)23-14-6-4-5-13(11-14)20(2,21)22)19(27)25(24-12)15-7-9-16(28-3)10-8-15/h4-11,17H,1-3H3,(H,23,26)
comment: Example 265 is an inhibitor of acetyl-CoA synthetase 2 (ACSS2) <Reference id=39746/>.
iupac name: N-[3-(1,1-difluoroethyl)phenyl]-1-(4-methoxyphenyl)-3-methyl-5-oxo-4H-pyrazole-4-carboxamide
approved: f
ligand name: example 265 [WO2019097515A1]
type: SyntheticOrganicLigand

(R)-CR8
in ch i key: HOCBJBNQIQQQGT-LJQANCHMSA-N
in ch i: InChI=1S/C24H29N7O/c1-4-19(14-32)28-24-29-22(21-23(30-24)31(15-27-21)16(2)3)26-13-17-8-10-18(11-9-17)20-7-5-6-12-25-20/h5-12,15-16,19,32H,4,13-14H2,1-3H3,(H2,26,28,29,30)/t19-/m1/s1
comment: CR8 is a small molecule inhibitor of cyclin-dependent kinases <Reference id=39740/>. It is structurally related to <Ligand id=6035/> (roscovitine). This entry is for the R isomer, which is more inhibitory at glycogen synthase kinase (GSK-3α/β) than the S isomer. Both isomers are equipotent across CDK1, 2, 5, 7, and 9. (R)-CR8 has been shown to act as a molecular glue degrader that depletes cyclin K <Reference id=39741/>, thus behaving as a functional CDK inhibitor. (R)-CR8 binding to CDK12 induces formation of a complex between CDK12-cyclin K and the CUL4 adaptor protein DDB1 which presents cyclin K for ubiquitination and degradation. Of the >8,000 proteins assessed by quantitative proteome-wide mass spectrometry, cyclin K was the only one that was consistently decreased in abundance in response to (R)-CR8 exposure.
iupac name: (2R)-2-[[9-propan-2-yl-6-[(4-pyridin-2-ylphenyl)methylamino]purin-2-yl]amino]butan-1-ol
xref: CHEMBL518800
approved: f
ligand name: (R)-CR8
type: SyntheticOrganicLigand

(S)-CR8
in ch i key: HOCBJBNQIQQQGT-IBGZPJMESA-N
in ch i: InChI=1S/C24H29N7O/c1-4-19(14-32)28-24-29-22(21-23(30-24)31(15-27-21)16(2)3)26-13-17-8-10-18(11-9-17)20-7-5-6-12-25-20/h5-12,15-16,19,32H,4,13-14H2,1-3H3,(H2,26,28,29,30)/t19-/m0/s1
comment: CR8 is a small molecule inhibitor of cyclin-dependent kinases <Reference id=39740/>. It is structurally related to <Ligand id=6035/> (roscovitine). This entry is for the S isomer, which is less inhibitory at glycogen synthase kinase (GSK-3α/β) than the R isomer. Both isomers are equipotent across CDK1, 2, 5, 7, and 9.
iupac name: (2S)-2-[[9-propan-2-yl-6-[(4-pyridin-2-ylphenyl)methylamino]purin-2-yl]amino]butan-1-ol
xref: CHEMBL1615221
approved: f
ligand name: (S)-CR8
type: SyntheticOrganicLigand

enteromycin carboxamide
canonical SMILES: CO/[N+](=C/C(=O)N/C=C/C(=O)N)/[O-]
isomeric SMILES: CO/[N+](=C/C(=O)N/C=C/C(=O)N)/[O-]
in ch i key: WWUHEQGWFDDSQX-DSXPNFDZSA-N
in ch i: InChI=1S/C6H9N3O4/c1-13-9(12)4-6(11)8-3-2-5(7)10/h2-4H,1H3,(H2,7,10)(H,8,11)/b3-2+,9-4+
comment: Enteromycin carboxamide is an antibacterial with in vitro Gram-negative and Gram-positive activity <Reference id=39733/>.
iupac name: 2-[[(E)-3-amino-3-oxoprop-1-enyl]amino]-N-methoxy-2-oxoethanimine oxide
synonym: LS-14645
synonym: BRN 2416858
synonym: BRN-2416858
synonym: BRN2416858
approved: f
ligand name: enteromycin carboxamide
type: SyntheticOrganicLigand

difficidin
canonical SMILES: C=C/C=C(/CCC1C/C=C/C=C(/C)/C(CCC/C=C/C=C/C=C/CC(C(=C)CC(=O)O1)C)OP(=O)(O)O)/C
isomeric SMILES: C=C/C=C(/CCC1C/C=C/C=C(/C)/C(CCC/C=C/C=C/C=C/CC(C(=C)CC(=O)O1)C)OP(=O)(O)O)/C
in ch i key: ZUWUQYGHRURWCL-XUIVTPDHSA-N
in ch i: InChI=1S/C31H45O6P/c1-6-17-25(2)22-23-29-20-16-15-19-27(4)30(37-38(33,34)35)21-14-12-10-8-7-9-11-13-18-26(3)28(5)24-31(32)36-29/h6-11,13,15-17,19,26,29-30H,1,5,12,14,18,20-24H2,2-4H3,(H2,33,34,35)/b9-7-,10-8-,13-11+,16-15+,25-17+,27-19+
comment: Difficidin is a macrocyclic polyene lactone phosphate ester originally isolated from Bacillus subtilis. It has potent antibacterial activity in vitro against a broad spectrum of aerobic and anaerobic organisms <Reference id=39734/>.
iupac name: [(4E,6E,12Z,14Z,16E)-7,19-dimethyl-2-[(3E)-3-methylhexa-3,5-dienyl]-20-methylidene-22-oxo-1-oxacyclodocosa-4,6,12,14,16-pentaen-8-yl] dihydrogen phosphate
approved: f
ligand name: difficidin
type: NaturalProductLigand

EHop 016
in ch i key: AFTZZRFCMOAFCR-UHFFFAOYSA-N
in ch i: InChI=1S/C25H30N6O/c1-2-31-22-7-4-3-6-20(22)21-18-19(8-9-23(21)31)28-24-10-12-27-25(29-24)26-11-5-13-30-14-16-32-17-15-30/h3-4,6-10,12,18H,2,5,11,13-17H2,1H3,(H2,26,27,28,29)
comment: Rac inhibitor.
iupac name: 4-N-(9-ethylcarbazol-3-yl)-2-N-(3-morpholin-4-ylpropyl)pyrimidine-2,4-diamine
xref: CHEMBL3237589
synonym: EHop016
synonym: EHop-016
approved: f
ligand name: EHop 016
type: SyntheticOrganicLigand

PF-956980
in ch i key: RONMOMUOZGIDET-HIFRSBDPSA-N
in ch i: InChI=1S/C18H26N6O/c1-13-6-10-24(18(25)23-8-3-4-9-23)11-15(13)22(2)17-14-5-7-19-16(14)20-12-21-17/h5,7,12-13,15H,3-4,6,8-11H2,1-2H3,(H,19,20,21)/t13-,15+/m1/s1
comment: PF-956980 is an ATP-competitive, reversible pan-JAK inhibitor <Reference id=25823/>. It is a useful commercially available JAK inhibitor tool. In addition to being an inhibitor of kinase activity, it is also reported to dose- and time-dependently reduce levels of JAK2/3 proteins (but not JAK1, as determined by Western blot) in human PBMCs, perhaps via modulating JAK2/3 synthesis <Reference id=39732/>. This latter activity seems to be unique to PF-956980, as there are no published reports of depletion of JAK isozymes by any of the other JAK inhibitors (such as <Ligand id=5677/>).
iupac name: [(3R,4R)-4-methyl-3-[methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino]piperidin-1-yl]-pyrrolidin-1-ylmethanone
xref: CHEMBL4068357
synonym: PF 956980
synonym: PF956980
synonym: PF-00956980
approved: f
ligand name: PF-956980
type: SyntheticOrganicLigand

EHT 1864
in ch i key: MIDUFIRTIFUTQA-UHFFFAOYSA-N
comment: Potent Rac family inhibitor. Marketed as EHT 1864 dihydrochloride.
iupac name: 2-(morpholin-4-ylmethyl)-5-[5-[7-(trifluoromethyl)quinolin-4-yl]sulfanylpentoxy]pyran-4-one
xref: CHEMBL1186585
synonym: EHT1864
synonym: EHT-1864
approved: f
ligand name: EHT 1864
type: SyntheticOrganicLigand

chalcomycin
in ch i key: KLGADJPDTCIJLO-FCNIXBKESA-N
in ch i: InChI=1S/C35H56O14/c1-17-10-13-26(37)46-20(4)22(16-44-34-32(43-9)31(42-8)27(38)21(5)47-34)30-23(48-30)11-12-25(36)35(6,40)15-18(2)29(17)49-33-28(39)24(41-7)14-19(3)45-33/h10-13,17-24,27-34,38-40H,14-16H2,1-9H3/b12-11+,13-10+/t17-,18-,19+,20+,21+,22+,23-,24-,27+,28+,29-,30-,31+,32+,33-,34+,35-/m0/s1
comment: Chalcomycin is a 16-membered macrolide antibacterial, originally isolated from Streptomyces.
iupac name: (1S,2R,3R,6E,8S,9R,10S,12S,14E,16S)-12-hydroxy-2-[[(2R,3R,4R,5R,6R)-5-hydroxy-3,4-dimethoxy-6-methyloxan-2-yl]oxymethyl]-9-[(2S,3R,4S,6R)-3-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy-3,8,10,12-tetramethyl-4,17-dioxabicyclo[14.1.0]heptadeca-6,14-diene-5,13-dione
approved: f
ligand name: chalcomycin
type: NaturalProductLigand

NSC 23766
in ch i key: DEFBCZWQLILOJF-UHFFFAOYSA-N
in ch i: InChI=1S/C24H35N7/c1-6-31(7-2)12-8-9-16(3)27-24-28-18(5)14-23(30-24)29-19-10-11-22-20(15-19)21(25)13-17(4)26-22/h10-11,13-16H,6-9,12H2,1-5H3,(H2,25,26)(H2,27,28,29,30)
comment: An inhibitor of the signalling G-protein known as Rac 1 (Ras-related C3 botulinum toxin substrate 1), where it acts as a selective inhibitor of Rac1-GEF interaction. Marketed as NSC 23766 trihydrochloride.
iupac name: N'-[2-(5-diethylaminopentan-2-ylamino)-6-methylpyrimidin-4-yl]-2-methylquinoline-4,6-diamine
xref: CHEMBL257119
synonym: NSC23766
synonym: NSC-23766
approved: f
ligand name: NSC 23766
type: SyntheticOrganicLigand

E-0702
in ch i key: IZPIFKHYHHWRMA-UHFFFAOYSA-N
comment: E-0702 is a cephalosporin derivative with antibacterial activity against clinical isolates of Gram-positive and Gram-negative bacteria, including the Pseudomonas group <Reference id=39728/>. Note that we show the salt stripped structure, but strictly E-0702 is the sodium salt (PubChem CID: 5748775) and any bioactivity data likely relates to this salt form.
iupac name: 3-[[1-(carboxymethyl)tetrazol-5-yl]sulfanylmethyl]-7-[[2-[(6,7-dihydroxy-4-oxochromene-3-carbonyl)amino]-2-(4-hydroxyphenyl)acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
approved: f
ligand name: E-0702
type: SyntheticOrganicLigand

ARN19874
in ch i key: OPBGIIQHYNFABO-UHFFFAOYSA-N
in ch i: InChI=1S/C19H14N4O4S/c24-18-16-11-15(5-6-17(16)21-19(25)22-18)28(26,27)23-14-3-1-12(2-4-14)13-7-9-20-10-8-13/h1-11,23H,(H2,21,22,24,25)
comment: ARN19874 is an inhibitor of N-acyl phosphatidylethanolamine phospholipase D (NAPE-PLD).
iupac name: 2,4-dioxo-N-(4-pyridin-4-ylphenyl)-1H-quinazoline-6-sulfonamide
synonym: HY-118994
synonym: CS-0078339
approved: f
ligand name: ARN19874
type: SyntheticOrganicLigand

faropenem
in ch i key: HGGAKXAHAYOLDJ-FHZUQPTBSA-N
in ch i: InChI=1S/C12H15NO5S/c1-5(14)7-10(15)13-8(12(16)17)9(19-11(7)13)6-3-2-4-18-6/h5-7,11,14H,2-4H2,1H3,(H,16,17)/t5-,6-,7+,11-/m1/s1
comment: Faropenem is a β-lactam antibacterial with Gram-negative activity. It was developed for the treatment of community acquired pneumonia.
iupac name: (5R,6S)-6-[(1R)-1-hydroxyethyl]-7-oxo-3-[(2R)-oxolan-2-yl]-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
xref: CHEMBL556262
synonym: fropenem
synonym: faropenem medoxomil
synonym: compound 1 [PMID: 9216830]
approved: f
ligand name: faropenem
type: SyntheticOrganicLigand

LEI-401
in ch i key: GFHJYPQZBBHOCC-UXHICEINSA-N
in ch i: InChI=1S/C24H31N5O2/c30-20-10-12-28(16-20)22-13-21(23(31)25-14-17-8-9-17)26-24(27-22)29-11-4-7-19(15-29)18-5-2-1-3-6-18/h1-3,5-6,13,17,19-20,30H,4,7-12,14-16H2,(H,25,31)/t19-,20+/m1/s1
comment: LEI-401 is a potent, selective and brain-penetrant inhibitor of N-Acylphosphatidylethanolamine-phospholipase D (NAPE-PLD) <Reference id=39722/>. It inhibits NAPE-PLD-mediated N-acylethanolamine (NAE) biosynthesis in vitro and in vivo, an effect that mimics the activity of a cannabinoid CB1 receptor antagonist.
iupac name: N-(cyclopropylmethyl)-6-[(3S)-3-hydroxypyrrolidin-1-yl]-2-[(3S)-3-phenylpiperidin-1-yl]pyrimidine-4-carboxamide
synonym: LEI401
approved: f
ligand name: LEI-401
type: SyntheticOrganicLigand

MUT056399
canonical SMILES: CCc1cc(O)c(cc1F)Oc1ccc(cc1F)C(=O)N
isomeric SMILES: CCc1cc(O)c(cc1F)Oc1ccc(cc1F)C(=O)N
in ch i key: QUHARGDBJJUOEB-UHFFFAOYSA-N
in ch i: InChI=1S/C15H13F2NO3/c1-2-8-6-12(19)14(7-10(8)16)21-13-4-3-9(15(18)20)5-11(13)17/h3-7,19H,2H2,1H3,(H2,18,20)
comment: MUT056399 is an inhibitor of bacterial Fabl, the NADH-dependent enoyl reductase from the type II bacterial fatty acid biosynthesis pathway <Reference id=39608/>.
iupac name: 4-(4-ethyl-5-fluoro-2-hydroxyphenoxy)-3-fluorobenzamide
xref: CHEMBL2178284
synonym: FAB001
synonym: MUT-056399
synonym: Fab-001
approved: f
ligand name: MUT056399
type: SyntheticOrganicLigand

luminamicin
in ch i key: UGSGHHXIPUAOBJ-FUQUDWCDSA-N
in ch i: InChI=1S/C32H38O12/c1-15-10-18-13-41-25(34)7-6-20-21(30(37)43-29(20)36)8-9-40-14-22(33)28(18)42-31(38)24(39-3)12-19-5-4-17-11-23-16(2)27(35)26(17)32(15,19)44-23/h4-5,8-10,16-19,22-24,26-28,33,35H,6-7,11-14H2,1-3H3/b9-8+,15-10+/t16-,17-,18?,19+,22?,23+,24?,26-,27+,28-,32-/m0/s1
comment: Luminamicin is an antibacterial that was isolated from actinomycete strain OMR-59 <Reference id=39720/>. It exhibits antibacterial activity against anaerobic bacteria, especially against Clostridium sp. <Reference id=39720/> <Reference id=39719/>. The chemical stuctures of luminamicin and coloradocin (from an Actinoplanes organism) are identical <Reference id=39719/>.
synonym: coloradocin
synonym: LS-90907
approved: f
ligand name: luminamicin
type: NaturalProductLigand

kaempferol
canonical SMILES: Oc1ccc(cc1)c1oc2cc(O)cc(c2c(=O)c1O)O
isomeric SMILES: Oc1ccc(cc1)c1oc2cc(O)cc(c2c(=O)c1O)O
in ch i key: IYRMWMYZSQPJKC-UHFFFAOYSA-N
in ch i: InChI=1S/C15H10O6/c16-8-3-1-7(2-4-8)15-14(20)13(19)12-10(18)5-9(17)6-11(12)21-15/h1-6,16-18,20H
comment: Kaempferol is a flavonol, a type of flavonoid, naturally occuring in a variety of plants. It has antibacterial activity against Gram-negative Helicobacter pylori and is reported to inhibit H. pylori HsrA (homeostatic stress regulator) <Reference id=39723/>.
iupac name: 3,5,7-trihydroxy-2-(4-hydroxyphenyl)chromen-4-one
xref: CHEMBL150
synonym: Robigenin
approved: f
ligand name: kaempferol
type: NaturalProductLigand

cefteram
in ch i key: XSPUSVIQHBDITA-RKYNPMAHSA-N
in ch i: InChI=1S/C16H17N9O5S2/c1-6-20-23-24(21-6)3-7-4-31-14-10(13(27)25(14)11(7)15(28)29)19-12(26)9(22-30-2)8-5-32-16(17)18-8/h5,10,14H,3-4H2,1-2H3,(H2,17,18)(H,19,26)(H,28,29)/b22-9-/t10-,14-/m1/s1
comment: Cefteram is a semisynthetic, broad-spectrum, third-generation oral cephalosporin antibacterial.
iupac name: (6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-[(5-methyltetrazol-2-yl)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
xref: CHEMBL2105953
synonym: CFTM
synonym: T-2525
synonym: Ro 19-5247
synonym: cefteram pivoxil (prodrug)
synonym: cefetamet
approved: f
ligand name: cefteram
type: SyntheticOrganicLigand

E-1010 free base
in ch i key: QYOLGBCSUXWEKY-ANTKKXPTSA-N
comment: E-1010 is a parenteral carbapenem antibacterial <Reference id=39715/>. LIke other carbapenems, it is resistant to hydrolysis by almost all clinically relevant β-lactamases.
iupac name: (4R,5S,6S)-6-[(1R)-1-hydroxyethyl]-3-[(3S,5S)-5-[(R)-hydroxy-[(3R)-pyrrolidin-3-yl]methyl]pyrrolidin-3-yl]sulfanyl-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
synonym: ER-35786
synonym: E1010
approved: f
ligand name: E-1010 free base
type: SyntheticOrganicLigand

SK&F 88070
in ch i key: ARWJIPOQKKRGCN-UPRLUYEASA-N
comment: SK&F 88070 is a broad-spectrum, β-lactam (cephalosporin) antibacterial <Reference id=39712/>.
iupac name: (6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-8-oxo-3-[[1-[2-(sulfoamino)ethyl]tetrazol-5-yl]sulfanylmethyl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
synonym: Skf 88070
approved: f
ligand name: SK&F 88070
type: SyntheticOrganicLigand

Ro-406890
in ch i key: RIBNLVJVYUATJJ-XPPPSQRSSA-N
in ch i: InChI=1S/C14H14N8O5S2/c1-27-20-7(6-4-29-14(15)18-6)10(23)19-8-11(24)22-9(13(25)26)5(2-17-21-16)3-28-12(8)22/h4,8,12H,2-3H2,1H3,(H2,15,18)(H,19,23)(H,25,26)/b20-7+/t8-,12-/m1/s1
comment: Ro-406890 is a broad spectrum cephalosporin antibacterial <Reference id=39709/>. We show the structure for the parent molecule. Biological data may have been generated using the sodium salt. It has also been synthesised as the orally absorbable ester Ro 41-3399 (a.k.a. ceftrazonal bopentil) <Reference id=39708/>.
iupac name: (6R,7R)-7-[[(2E)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-(azidomethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
synonym: Ro406890
synonym: ceftrazonal
synonym: Ro 406890
synonym: Ro 40-6890
approved: f
ligand name: Ro-406890
type: SyntheticOrganicLigand

M14659
in ch i key: PBJHSJKHPMHQSC-XIMWIQTNSA-N
comment: M14659 is a parenteral cephalosporin antibacterial <Reference id=39707/>. We show he structure for the parent molecule. Biological data may have been generated using the trisodium salt.
iupac name: (6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-5-yl)-2-[(S)-carboxy-(3,4-dihydroxyphenyl)methoxy]iminoacetyl]amino]-3-[(2-carboxy-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
synonym: M-14659
synonym: M 14659
synonym: GR 63116
synonym: GR-63116
approved: f
ligand name: M14659
type: SyntheticOrganicLigand

KB-5246
in ch i key: BVTDWOWPDCPIOM-UHFFFAOYSA-N
in ch i: InChI=1S/C18H18FN3O4S/c1-21-2-4-22(5-3-21)15-14(19)8-6-10(23)13(18(24)25)17-11(8)12-9(20-27-17)7-26-16(12)15/h11-12H,2-7H2,1H3,(H,24,25)
comment: KB-5246 is a tetracyclic quinolone antibacterial <Reference id=39706/> This structure represents the KB-5246 parent molecule. Experimental evidence may relate to the hydrochloride.
synonym: LS-99630
synonym: KB5246
approved: f
ligand name: KB-5246
type: SyntheticOrganicLigand

ME-1228 acid
in ch i key: HJXPKHCLLLRQDL-HFCXZPKYSA-O
in ch i: InChI=1S/C23H24N6O7S3/c1-3-28-6-4-13(5-7-28)37-8-12-9-38-20-16(19(31)29(20)17(12)22(34)35)26-18(30)15(14-10-39-23(24)25-14)27-36-11(2)21(32)33/h4-7,10-11,16,20H,3,8-9H2,1-2H3,(H4-,24,25,26,30,32,33,34,35)/p+1/b27-15+/t11-,16+,20+/m0/s1
comment: ME1228 is a parenteral cephalosporin antibacterial <Reference id=39704/>. It is sensitive to hydrolysis by TEM-3 and Xanthomonas maltophilia β-lactamases.
iupac name: (6R,7R)-7-[[(2E)-2-(2-amino-1,3-thiazol-4-yl)-2-[(1S)-1-carboxyethoxy]iminoacetyl]amino]-3-[(1-ethylpyridin-1-ium-4-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
synonym: ME1228
approved: f
ligand name: ME-1228 acid
type: SyntheticOrganicLigand

chlorocardicin
in ch i key: UMDAIHWMUXNVSB-IMUCLJOZSA-N
in ch i: InChI=1S/C23H23ClN4O9/c24-14-9-12(3-6-17(14)29)19(23(34)35)28-10-16(21(28)31)26-20(30)18(27-36)11-1-4-13(5-2-11)37-8-7-15(25)22(32)33/h1-6,9,15-16,19,29,36H,7-8,10,25H2,(H,26,30)(H,32,33)(H,34,35)/b27-18+/t15-,16+,19-/m1/s1
comment: Chlorocardicin is a monocyclic β-lactam produced by Streptomyces sp. <Reference id=39701/><Reference id=39702/>. It is structurally related to nocardicin A, and has a similar activity profile.
iupac name: (2R)-2-amino-4-[4-[(E)-C-[[(3S)-1-[(R)-carboxy-(3-chloro-4-hydroxyphenyl)methyl]-2-oxoazetidin-3-yl]carbamoyl]-N-hydroxycarbonimidoyl]phenoxy]butanoic acid
approved: f
ligand name: chlorocardicin
type: NaturalProductLigand

LBM-415
in ch i key: AYCMYBACERJYNY-HIFRSBDPSA-N
in ch i: InChI=1S/C18H25FN4O5/c1-2-3-5-13(10-21(27)12-24)18(26)22-9-4-6-15(22)17(25)20-16-8-7-14(19)11-23(16)28/h7-8,11-13,15,27-28H,2-6,9-10H2,1H3/t13-,15+/m1/s1
comment: LBM-415 is an antibacterial that acts as a peptide deformylase (PDF) inhibitor <Reference id=39699/>. It has in vitro activity against pathogenic staphylococci and enterococci, including respiratory tract pathogens such as Streptococcus pneumoniae, Haemophilus influenzae, and Moraxella catarrhalis <Reference id=39696/><Reference id=39697/><Reference id=39698/>.
xref: CHEMBL221667
synonym: LBM415
synonym: NVP-PDF-713
synonym: PDF-713
synonym: NVP LBM-415
approved: f
ligand name: LBM-415
type: SyntheticOrganicLigand

vermisporin
in ch i key: OBDFYDGODWWFEX-UDEGNFRISA-N
in ch i: InChI=1S/C25H37NO4/c1-12(2)21-23(28)20(24(29)26(21)7)22(27)19-17(25(6)15(5)30-25)9-8-16-11-13(3)10-14(4)18(16)19/h8-9,12-19,21,27H,10-11H2,1-7H3/b22-20-/t13-,14+,15-,16-,17?,18+,19+,21-,25+/m0/s1
comment: Vermisporin is an antibacterial produced by the fungus Ophiobolus vermisporis <Reference id=39631/>. It has Gram-negative and Gram-positive activity, and has antitubercular activity <Reference id=39632/>.
iupac name: (3Z,5S)-3-[[(1S,4aR,6S,8R,8aR)-2-[(2S,3S)-2,3-dimethyloxiran-2-yl]-6,8-dimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]-hydroxymethylidene]-1-methyl-5-propan-2-ylpyrrolidine-2,4-dione
approved: f
ligand name: vermisporin
type: NaturalProductLigand

L-701677
in ch i key: CVVWWIGGJJALDG-CFLXSVEWSA-N
in ch i: InChI=1S/C38H72N2O12/c1-15-27-38(10,46)31(42)20(2)19-40(13)21(3)17-36(8,45)33(52-35-29(41)26(39(11)12)16-22(4)48-35)23(5)30(24(6)34(44)50-27)51-28-18-37(9,47-14)32(43)25(7)49-28/h20-33,35,41-43,45-46H,15-19H2,1-14H3/t20-,21+,22+,23-,24+,25-,26-,27+,28-,29+,30-,31+,32-,33+,35-,36+,37+,38+/m0/s1
comment: L-701677is an azalide antibacterial that was developed by Merck. It has improved acid stability compared to <Ligand id=1456/>, <Ligand id=6510/> and <Ligand id=10903/>.
iupac name: (2R,3S,4R,5S,8R,10R,11R,12S,13S,14R)-11-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-2-ethyl-3,4,10-trihydroxy-13-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-3,5,7,8,10,12,14-heptamethyl-1-oxa-7-azacyclopentadecan-15-one
xref: CHEMBL273931
synonym: L-701,677
approved: f
ligand name: L-701677
type: SyntheticOrganicLigand

leinamycin
in ch i key: ZHTRILQJTPJGNK-FYBAATNNSA-N
in ch i: InChI=1S/C22H26N2O6S3/c1-13-8-9-22(21(3,29)20(28)32-33(22)30)11-18(27)23-14(2)19-24-15(12-31-19)6-4-5-7-16(25)17(26)10-13/h4-7,10,12,14,17,26,29H,8-9,11H2,1-3H3,(H,23,27)/b6-4-,7-5+,13-10+/t14-,17-,21+,22-,33?/m1/s1
comment: Leinamycin is a macrolactam antibacterial (activity against Gram-positive and gram-negative bacteria) that also has potent anti-tumour activity <Reference id=39691/><Reference id=39692/><Reference id=39694/>. It is produced by several species of Streptomyces atroolivaceus. Cytotoxicity against cancer cells hinges upon the compound's 1,3-dioxo-1,2-dithiolane moiety <Reference id=39693/>.
iupac name: (2R,4'R,6R,9E,11R,13E,15Z)-4',11-dihydroxy-2,4',9-trimethyl-1'-oxospiro[19-thia-3,20-diazabicyclo[15.2.1]icosa-1(20),9,13,15,17-pentaene-6,5'-dithiolane]-3',4,12-trione
xref: CHEMBL360089
synonym: DC107
synonym: DC-107
approved: f
ligand name: leinamycin
type: NaturalProductLigand

DX-619
in ch i key: ZLICIITZJTYKAQ-DIOULYMOSA-N
in ch i: InChI=1S/C21H24FN3O4/c1-29-19-15(24-7-4-11(9-24)21(23)5-6-21)3-2-12-17(19)25(16-8-14(16)22)10-13(18(12)26)20(27)28/h2-3,10-11,14,16H,4-9,23H2,1H3,(H,27,28)/t11-,14+,16-/m1/s1
comment: DX-619 is a des-fluoroquinolone antibacterial <Reference id=39688/><Reference id=39689/>.
iupac name: 7-[(3R)-3-(1-aminocyclopropyl)pyrrolidin-1-yl]-1-[(1R,2S)-2-fluorocyclopropyl]-8-methoxy-4-oxoquinoline-3-carboxylic acid
xref: CHEMBL390983
synonym: compound 4 [PMID: 19736016]
synonym: DX619
approved: f
ligand name: DX-619
type: SyntheticOrganicLigand

sorangicin A
in ch i key: OTABDKFPJQZJRD-QLGZCQHWSA-N
in ch i: InChI=1S/C47H66O11/c1-30(17-14-15-23-44(50)51)27-31(2)47-40-26-25-34(54-47)18-10-6-5-7-11-19-35(48)46(53)43-28-36(49)32(3)37(56-43)21-16-22-38-33(4)41-29-42(55-38)39(57-41)20-12-8-9-13-24-45(52)58-40/h6,8-13,16,19-20,22,24-27,30,32-43,46-49,53H,5,7,14-15,17-18,21,23,28-29H2,1-4H3,(H,50,51)/b9-8-,10-6+,19-11+,20-12+,22-16+,24-13-,31-27+/t30-,32-,33+,34+,35+,36+,37-,38+,39-,40+,41-,42-,43-,46+,47+/m1/s1
comment: Originally isolated from Sorangium cellulosum, sorangicin A is a macrocyclic lactone carbonic acid with potent activity against Gram-positive bacteria <Reference id=39753/>.
synonym: (+)-Sorangicin A
approved: f
ligand name: sorangicin A
type: SyntheticOrganicLigand

DK-507k
in ch i key: JYRHGXXQSIPDDP-IACUBPJLSA-N
in ch i: InChI=1S/C20H21F2N3O4/c1-29-18-15-9(17(26)10(19(27)28)6-25(15)13-5-11(13)21)4-12(22)16(18)24-7-14(23)20(8-24)2-3-20/h4,6,11,13-14H,2-3,5,7-8,23H2,1H3,(H,27,28)/t11-,13+,14+/m0/s1
comment: DK-507k is a fluoroquinolone antibacterial. Compared to earlier generation fluoroquinolones it has improved activity against Gram-positive bacteria, including strains resistant to available quinolones <Reference id=39686/>. DK-507k was being investigated as a potential treatment for community-acquired infections, but development has been discontinued following an analysis of Phase I trial data.
iupac name: 7-[(4S)-4-amino-6-azaspiro[2.4]heptan-6-yl]-6-fluoro-1-[(1R,2S)-2-fluorocyclopropyl]-8-methoxy-4-oxoquinoline-3-carboxylic acid
xref: CHEMBL2365143
approved: f
ligand name: DK-507k
type: SyntheticOrganicLigand

BRL-44154
in ch i key: KNTUUEGDGYZCIA-ZUPSXRMKSA-N
in ch i: InChI=1S/C19H25N5O5S2/c1-19(2)14(17(27)28)24-12(25)7-10(16(24)31-19)21-15(26)13(11-8-30-18(20)22-11)23-29-9-5-3-4-6-9/h8-10,14,16H,3-7H2,1-2H3,(H2,20,22)(H,21,26)(H,27,28)/b23-13+/t10-,14+,16-/m1/s1
comment: Strictly this is the parent molecule of BRL-44154 which referes to the sodium salt. BRL-44154 is a penicillin class antibacterial that was developed by SmithKline Beecham <Reference id=39681/>. It has high stability to β-lactamases.
iupac name: (3S,7R,7aR)-7-[[(2E)-2-(2-amino-1,3-thiazol-4-yl)-2-cyclopentyloxyiminoacetyl]amino]-2,2-dimethyl-5-oxo-3,6,7,7a-tetrahydropyrrolo[2,1-b][1,3]thiazole-3-carboxylic acid
synonym: analogue 4f [Brown et al., 1991]
synonym: BRL44154
approved: f
ligand name: BRL-44154
type: SyntheticOrganicLigand

retapamulin
in ch i key: STZYTFJPGGDRJD-FJJJPKKESA-N
in ch i: InChI=1S/C30H47NO4S/c1-7-28(4)16-24(35-25(33)17-36-22-14-20-8-9-21(15-22)31(20)6)29(5)18(2)10-12-30(19(3)27(28)34)13-11-23(32)26(29)30/h7,18-22,24,26-27,34H,1,8-17H2,2-6H3/t18-,19+,20-,21+,22?,24-,26+,27+,28-,29+,30+/m1/s1
comment: Retapamulin is a pleuromutilin antibacterial <Reference id=39679/>.
xref: CHEMBL1658
synonym: Altabax®
synonym: SB-275833
synonym: SB275833
synonym: Altargo®
approved: t
ligand name: retapamulin
type: SyntheticOrganicLigand

BC-7013
in ch i key: NOQBAJLIGCZEQP-CREOWZIVSA-N
in ch i: InChI=1S/C29H40O5S/c1-6-27(4)15-23(34-24(32)17-35-21-9-7-20(16-30)8-10-21)28(5)18(2)11-13-29(19(3)26(27)33)14-12-22(31)25(28)29/h6-10,18-19,23,25-26,30,33H,1,11-17H2,2-5H3/t18?,19-,23+,25?,26-,27+,28-,29-/m0/s1
comment: BC-7013 is a pleuromutilin antibacterial. The chemical structure shown here was drawn from Tang et al. (2012) <Reference id=39677/><Reference id=39604/>. In 2007 <Ligand id=11035/> became the first pleuromutilin approved for use in humans, and <Ligand id=10824/> was FDA approved in 2019.
synonym: BC7013
approved: f
ligand name: BC-7013
type: SyntheticOrganicLigand

MC-02479
in ch i key: LTUWUNMGTLOPNC-UHFFFAOYSA-N
comment: MC-02479 (RWJ-54428) is a cephalosporin antibacterial with Gram-positive activity <Reference id=39674/><Reference id=39675/>.
iupac name: 7-[[2-(2-amino-5-chloro-1,3-thiazol-4-yl)-2-hydroxyiminoacetyl]amino]-3-[3-(2-aminoethylsulfanylmethyl)pyridin-4-yl]sulfanyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
synonym: RWJ-54428
synonym: RWJ 54428
synonym: MC 02479
synonym: MC02479
approved: f
ligand name: MC-02479
type: SyntheticOrganicLigand

levopropicillin
in ch i key: HOCWPKXKMNXINF-RSUWNVLCSA-N
in ch i: InChI=1S/C18H22N2O5S/c1-4-11(25-10-8-6-5-7-9-10)14(21)19-12-15(22)20-13(17(23)24)18(2,3)26-16(12)20/h5-9,11-13,16H,4H2,1-3H3,(H,19,21)(H,23,24)/t11-,12+,13-,16+/m0/s1
comment: Levopropicillin (levopropylcillin) is a penicillin type antibacterial, with activity against Staphylococci but it is not stable to penicillinase.
iupac name: (2S,5R,6R)-3,3-dimethyl-7-oxo-6-[[(2S)-2-phenoxybutanoyl]amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
xref: CHEMBL3990988
synonym: BRL-284
synonym: BRL284
synonym: P-248
synonym: P248
synonym: L-Propicillin
approved: f
ligand name: levopropicillin
type: SyntheticOrganicLigand

delpazolid
in ch i key: QLUWQAFDTNAYPN-LLVKDONJSA-N
in ch i: InChI=1S/C14H17FN4O3/c1-17-4-5-18(9-16-17)13-3-2-10(6-12(13)15)19-7-11(8-20)22-14(19)21/h2-3,6,9,11,20H,4-5,7-8H2,1H3/t11-/m1/s1
comment: CB01-0371 is an oxazolidinone antibacterial <Reference id=39606/> that was developed for antitubercular activity.
iupac name: (5R)-3-[3-fluoro-4-(1-methyl-5,6-dihydro-1,2,4-triazin-4-yl)phenyl]-5-(hydroxymethyl)-1,3-oxazolidin-2-one
xref: CHEMBL1673408
synonym: LCB01-0371
synonym: LCB-01,0371
synonym: LCB-01-0371
approved: f
ligand name: delpazolid
type: SyntheticOrganicLigand

IT-62-B
in ch i key: JVRLFIBJALHFAP-JLHPLHHJSA-N
in ch i: InChI=1S/C39H47NO15/c1-15(14-41)35-37(48)40-22-11-26(51-17(3)36(22)54-25(10-16(2)42)52-18(4)38(40)55-35)53-24-13-39(49,19(5)43)12-21-28(24)34(47)30-29(32(21)45)31(44)20-8-7-9-23(50-6)27(20)33(30)46/h7-9,15-18,22,24-26,35-36,38,41-42,45,47,49H,10-14H2,1-6H3/t15?,16?,17-,18?,22-,24-,25?,26?,35?,36+,38?,39-/m0/s1
comment: IT-62-B is an anthracycline antibacterial that is produced by Streptomyces sp. IT-62 <Reference id=39672/><Reference id=39673/>. It has moderate activity against Gram-positive bacteria and has antitumour activity in vitro.
iupac name: (7S,9S)-9-acetyl-6,9,11-trihydroxy-7-[[(1S,11S,12S)-4-(1-hydroxypropan-2-yl)-9-(2-hydroxypropyl)-7,12-dimethyl-3-oxo-5,8,10,13-tetraoxa-2-azatricyclo[9.4.0.02,6]pentadecan-14-yl]oxy]-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione
approved: f
ligand name: IT-62-B
type: SyntheticOrganicLigand

Sch 29482
canonical SMILES: CCSC1=C(C(=O)O)N2[C@H](S1)C(C2=O)C(O)C
isomeric SMILES: CCSC1=C(C(=O)O)N2[C@H](S1)C(C2=O)C(O)C
in ch i key: LDVDKTLZRGWFID-MPKXYMLHSA-N
in ch i: InChI=1S/C10H13NO4S2/c1-3-16-10-6(9(14)15)11-7(13)5(4(2)12)8(11)17-10/h4-5,8,12H,3H2,1-2H3,(H,14,15)/t4?,5?,8-/m1/s1
comment: Sch 29482 is a penem antibacterial belonging to the β-lactam group. It is orally absorbed, has activity against both Gram-positive and Gram-negative bacteria (with the exception of Pseudomonas) and exhibits β-lactamase stability <Reference id=39678/><Reference id=39680/><Reference id=39684/><Reference id=39685/>. Sch 29482 has been dropped from developed for clinical use <Reference id=39683/>.
iupac name: (5R)-3-ethylsulfanyl-6-(1-hydroxyethyl)-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
approved: f
ligand name: Sch 29482
type: SyntheticOrganicLigand

Corallopyronin A
canonical SMILES: C/C=C/C/C=C(/C(CC/C(=C/C=C(/C(=O)c1c(O)cc(oc1=O)C(CC/C=C/NC(=O)OC)C)/C)/C)O)/C
isomeric SMILES: C/C=C/C/C=C(/C(CC/C(=C/C=C(/C(=O)c1c(O)cc(oc1=O)C(CC/C=C/NC(=O)OC)C)/C)/C)O)/C
in ch i key: FPBHSTHTCPCNBS-QXMYDWGFSA-N
in ch i: InChI=1S/C30H41NO7/c1-7-8-9-12-21(3)24(32)17-15-20(2)14-16-23(5)28(34)27-25(33)19-26(38-29(27)35)22(4)13-10-11-18-31-30(36)37-6/h7-8,11-12,14,16,18-19,22,24,32-33H,9-10,13,15,17H2,1-6H3,(H,31,36)/b8-7+,18-11+,20-14+,21-12+,23-16+
comment: Corallopyronin A is a polyketide-peptide antibacterial produced by myxobacterium Corallococcus coralloides B035 <Reference id=39663/><Reference id=39665/><Reference id=39668/>. It has potent anti-filarial activity <Reference id=39666/><Reference id=39667/>.
iupac name: methyl N-[(E)-5-[4-hydroxy-5-[(2E,4E,9E,12E)-8-hydroxy-2,5,9-trimethyltetradeca-2,4,9,12-tetraenoyl]-6-oxopyran-2-yl]hex-1-enyl]carbamate
synonym: LS-54950
synonym: LS54950
synonym: CorA
approved: f
ligand name: Corallopyronin A
type: NaturalProductLigand

TNP-2092
in ch i key: OPZFMLLAJBIKAN-KYGXCNJYSA-N
in ch i: InChI=1S/C65H81FN6O15/c1-31-13-12-14-32(2)61(80)68-50-44(56(77)47-48(57(50)78)55(76)37(7)59-49(47)60(79)64(9,87-59)85-26-20-46(84-11)33(3)58(86-38(8)73)36(6)54(75)35(5)53(31)74)28-67-71-24-18-41(19-25-71)69(10)65(21-22-65)40-17-23-70(29-40)52-34(4)51-42(39-15-16-39)27-43(63(82)83)62(81)72(51)30-45(52)66/h12-14,20,26-28,30-31,33,35-36,39-41,46,53-54,58,74-78H,15-19,21-25,29H2,1-11H3,(H,68,80)(H,82,83)/b13-12+,26-20+,32-14-,67-28+/t31-,33+,35+,36+,40+,46-,53-,54+,58+,64-/m0/s1
comment: TNP-2092 (formerly CBR-2092) is a rifamycin-quinolone hybrid antibacterial compound <Reference id=39661/>. It exerts combined effects on bacterial RNA polymerase, DNA gyrase and DNA topoisomerase IV, although RNA polymerase has been reporetd as the primary cellular target <Reference id=39659/>. CBR-2092 was developed for potential to treat biofilm associated infections such as those caused by staphylococci <Reference id=39658/><Reference id=39659/>. Initial development was by Cumbre Pharmaceuticals, but it is now being taken forward by TenNor Therapeutics, hence the change in research code.
synonym: TNP2092
synonym: CBR2092
synonym: CBR-2092
approved: f
ligand name: TNP-2092
type: SyntheticOrganicLigand

oleuropein
in ch i key: RFWGABANNQMHMZ-ZCHJGGQASA-N
in ch i: InChI=1S/C25H32O13/c1-3-13-14(9-19(29)35-7-6-12-4-5-16(27)17(28)8-12)15(23(33)34-2)11-36-24(13)38-25-22(32)21(31)20(30)18(10-26)37-25/h3-5,8,11,14,18,20-22,24-28,30-32H,6-7,9-10H2,1-2H3/b13-3+/t14-,18+,20+,21-,22+,24-,25-/m0/s1
comment: Oleuropein is one of the main phenolic compounds found in the European olive tree Olea europaea. It has been reported to have a number of pharmacological properties and associated health benefits including anti-inflammatory, anti-atherogenic, anti-cancer, antimicrobial and antiviral activities <Reference id=39660/>. Oleuropein and its metabolite hydroxytyrosol have been shown to have strong antimicrobial activity against both Gram-negative and Gram-positive bacteria <Reference id=39664/>.
iupac name: methyl (4S,5E,6S)-4-[2-[2-(3,4-dihydroxyphenyl)ethoxy]-2-oxoethyl]-5-ethylidene-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4H-pyran-3-carboxylate
xref: CHEMBL1911053
approved: f
ligand name: oleuropein
type: NaturalProductLigand

NBI-35965
in ch i key: SUCZRVASFXLXDM-HNNXBMFYSA-N
in ch i: InChI=1S/C21H22Cl2N4/c1-3-15-11-27-21-18(26(15)10-13-4-5-13)8-12(2)24-20(21)19(25-27)16-7-6-14(22)9-17(16)23/h6-9,13,15H,3-5,10-11H2,1-2H3/t15-/m0/s1
comment: Potent and selective CRF1 receptor antagonist, Marketed as NBI 35965 hydrochloride.
iupac name: (10S)-9-(cyclopropylmethyl)-3-(2,4-dichlorophenyl)-10-ethyl-6-methyl-1,2,5,9-tetrazatricyclo[6.3.1.0^4,12]dodeca-2,4,6,8(12)-tetraene
xref: CHEMBL380800
synonym: NBI35965
synonym: NBI 35965
approved: f
ligand name: NBI-35965
type: SyntheticOrganicLigand

BMS-986235
in ch i key: FJZNNKJZHQFMCK-LRDDRELGSA-N
in ch i: InChI=1S/C18H17F2N3O3/c1-26-11-7-13(19)15(14(20)8-11)12-9-21-17(24)16(12)23-18(25)22-10-5-3-2-4-6-10/h2-8,12,16H,9H2,1H3,(H,21,24)(H2,22,23,25)/t12-,16-/m0/s1
comment: BMS-986235 (LAR-1219) is a selective formyl peptide receptor 2 (FPR2) agonist <Reference id=39650/>. It is being proposed as a preventative heart failure agent, via promoting resolution of inflammation.
iupac name: 1-[(3S,4R)-4-(2,6-difluoro-4-methoxyphenyl)-2-oxopyrrolidin-3-yl]-3-phenylurea
synonym: BMS986235
synonym: LAR-1219
synonym: LAR1219
synonym: compound 13c [PMID: 32407089]
approved: f
ligand name: BMS-986235
type: SyntheticOrganicLigand

DS-1971a
in ch i key: OJKONCJPCULNOW-DYVFJYSZSA-N
comment: DS-1971a is a selective NaV1.7 inhibitor that was developed for peripheral neuropathic pain <Reference id=39649/>.
iupac name: 5-chloro-2-fluoro-4-[(1S,2R)-2-(2-methylpyrazol-3-yl)cyclohexyl]oxy-N-pyrimidin-4-ylbenzenesulfonamide
synonym: compound 6o [PMID: 32392056]
approved: f
ligand name: DS-1971a
type: SyntheticOrganicLigand

lactivicin
canonical SMILES: CC(=O)NC1CON(C1=O)C1(CCC(=O)O1)C(=O)O
isomeric SMILES: CC(=O)NC1CON(C1=O)C1(CCC(=O)O1)C(=O)O
in ch i key: ZUEKKUYIXILDAF-UHFFFAOYSA-N
in ch i: InChI=1S/C10H12N2O7/c1-5(13)11-6-4-18-12(8(6)15)10(9(16)17)3-2-7(14)19-10/h6H,2-4H2,1H3,(H,11,13)(H,16,17)
comment: Lactivicin is the only known natural penicillin-binding protein inhibitor that does not contain a β-lactam structure <Reference id=39648/>.
iupac name: 2-(4-acetamido-3-oxo-1,2-oxazolidin-2-yl)-5-oxooxolane-2-carboxylic acid
xref: CHEMBL1909427
synonym: compound 1 [PMID: 17676039]
synonym: LTV
approved: f
ligand name: lactivicin
type: NaturalProductLigand

indolmycin
in ch i key: GNTVWGDQPXCYBV-PELKAZGASA-N
in ch i: InChI=1S/C14H15N3O2/c1-8(12-13(18)17-14(15-2)19-12)10-7-16-11-6-4-3-5-9(10)11/h3-8,12,16H,1-2H3,(H,15,17,18)/t8-,12+/m1/s1
comment: Indolmycin competitively inhibits bacterial tryptophanyl-tRNA synthetases. It has antibacterial activity against MSSA (methicillin-susceptible Staphylococcus aureus), MRSA (methicillin-resistant S. aureus) and VISA (vancomycin-intermediate S. aureus) <Reference id=39647/>. The compound also has antimalarial activity <Reference id=40889/>. The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
iupac name: (5S)-5-[(1R)-1-(1H-indol-3-yl)ethyl]-2-methylimino-1,3-oxazolidin-4-one
xref: CHEMBL417852
synonym: PA 155 A
synonym: PA-155A
synonym: TAK-083
synonym: PA-155-A
approved: f
ligand name: indolmycin
type: SyntheticOrganicLigand

tirandalydigin
in ch i key: LTYHWFXVSQHTQH-BWPJEIAHSA-N
in ch i: InChI=1S/C22H27NO6/c1-12(5-6-15(24)18-16(25)10-23-20(18)26)9-13(2)19-14(3)17-7-8-22(11-27-22)21(4,28-17)29-19/h5-9,13-14,17,19,24H,10-11H2,1-4H3,(H,23,26)/b6-5+,12-9+,18-15-/t13-,14+,17-,19-,21-,22?/m1/s1
comment: Tirandalydigin is a tetramic acid antibacterial produced by Streptomyces tirandis subsp. umidus. <Reference id=39634/><Reference id=39635/>.
iupac name: (3Z)-3-[(2E,4E,6R)-6-[(1R,3R,4S,5R)-1,4-dimethylspiro[2,9-dioxabicyclo[3.3.1]non-6-ene-8,2'-oxirane]-3-yl]-1-hydroxy-4-methylhepta-2,4-dienylidene]pyrrolidine-2,4-dione
approved: f
ligand name: tirandalydigin
type: NaturalProductLigand

dactimicin
in ch i key: VFBPKQSATYZKRX-WKEGKRRDSA-N
in ch i: InChI=1S/C18H36N6O6/c1-8(20)10-5-4-9(21)18(29-10)30-16-12(22)14(26)17(28-3)13(15(16)27)24(2)11(25)6-23-7-19/h7-10,12-18,26-27H,4-6,20-22H2,1-3H3,(H2,19,23)/t8-,9+,10-,12-,13-,14-,15+,16+,17+,18+/m0/s1
comment: Dactimicin is an aminoglycoside antibacterial produced by Dactylosporangium matsuzakiense sp. nov.<Reference id=39610/><Reference id=39611/>.
iupac name: N-[(1S,2R,3R,4S,5S,6R)-4-amino-3-[(2R,3R,6S)-3-amino-6-[(1S)-1-aminoethyl]oxan-2-yl]oxy-2,5-dihydroxy-6-methoxycyclohexyl]-2-(aminomethylideneamino)-N-methylacetamide
synonym: Formimidoyl-fortimicin A
synonym: SF-2052
synonym: SF2052
approved: f
ligand name: dactimicin
type: NaturalProductLigand

plusbacin A3
in ch i key: RRAOZJHXDSMGMH-LOKPQUDHSA-N
comment: Plusbacin A3 was isolated from Pseudomonas sp. PB-6250 <Reference id=39644/>. It acts as a peptidoglycan synthesis inhibitor in methicillin-resistant Staphylococcus aureus <Reference id=39643/>. Plusbacin A3 can be chemically synthesised <Reference id=39645/>.
approved: f
ligand name: plusbacin A3
type: NaturalProductLigand

nodusmicin
in ch i key: LUCYVUUQBYQHOV-GFCOOTNGSA-N
in ch i: InChI=1S/C23H34O7/c1-10-8-11(2)23-14(9-16(28-5)22(27)29-20(10)13(4)24)6-7-15-17(23)18(25)12(3)19(26)21(15)30-23/h6-8,10,12-21,24-26H,9H2,1-5H3/b11-8-/t10-,12-,13-,14-,15-,16+,17+,18-,19-,20+,21-,23+/m1/s1
comment: Nodusmicin is an antibacterial produced by the soil-dwelling organism Saccharopolyspors kirsuta strain 367 <Reference id=39642/>. It has activity against Gram-negative and Gram-positive bacteria.
synonym: nodusmicin 1
approved: f
ligand name: nodusmicin
type: NaturalProductLigand

vertilmicin
in ch i key: QVRLHIRFLRXFIW-OFMFRWEUSA-N
in ch i: InChI=1S/C22H43N5O7/c1-5-27-13-8-12(25)17(33-20-11(24)6-7-14(32-20)10(2)23)15(28)18(13)34-21-16(29)19(26-4)22(3,30)9-31-21/h7,10-13,15-21,26-30H,5-6,8-9,23-25H2,1-4H3/t10?,11-,12+,13-,15+,16-,17-,18+,19-,20-,21-,22+/m1/s1
comment: Vertilmicin is a semisynthetic aminoglycoside antibacterial that inhibits bacterial growth by inhibiting protein synthesis. It has Gram-negative and Gram-positive activity <Reference id=39444/>.
iupac name: (2R,3R,4R,5R)-2-[(1S,2S,3R,4S,6R)-4-amino-3-[[(2S,3R)-3-amino-6-(1-aminoethyl)-3,4-dihydro-2H-pyran-2-yl]oxy]-6-(ethylamino)-2-hydroxycyclohexyl]oxy-5-methyl-4-(methylamino)oxane-3,5-diol
approved: f
ligand name: vertilmicin
type: SyntheticOrganicLigand

chinfloxacin
in ch i key: KNLARSZRTBDTIA-UHFFFAOYSA-N
in ch i: InChI=1S/C21H22F3N3O4/c22-14-6-12-16(27(11-3-4-11)8-13(18(12)28)20(29)30)19(31-21(23)24)17(14)26-7-10-2-1-5-25-15(10)9-26/h6,8,10-11,15,21,25H,1-5,7,9H2,(H,29,30)
comment: Chinfloxacin is a synthetic tricyclic fluoroquinolone antibacterial <Reference id=39640/>. Its chemical structure is similar to that of <Ligand id=10915/>.
iupac name: 7-(1,2,3,4,4a,5,7,7a-octahydropyrrolo[3,4-b]pyridin-6-yl)-1-cyclopropyl-8-(difluoromethoxy)-6-fluoro-4-oxoquinoline-3-carboxylic acid
approved: f
ligand name: chinfloxacin
type: SyntheticOrganicLigand

kibdelomycin A
in ch i key: ZPMXCTSMZFCELU-DEIVJSAASA-N
comment: Kibdelomycin is a broad-spectrum bactericidal agent with activity against aerobic bacteria <Reference id=39638/>. It inhibits bacterial growth by inhibiting the bacterial DNA replication enzymes DNA gyrase and topoisomerase IV.
iupac name: [(2S,3S,4S,5S,6R)-2-[(3Z,5S)-3-[[(2S,4aR,5R,8aS)-5-[(2R,4R,5R,6R)-4-[(1S)-1-[(3,4-dichloro-1H-pyrrole-2-carbonyl)amino]ethyl]-4,5-dihydroxy-6-methyloxan-2-yl]oxy-2-methyl-8-methylidene-2,4a,5,6,7,8a-hexahydro-1H-naphthalen-1-yl]-hydroxymethylidene]-2,4-dioxo-5-propan-2-ylpyrrolidin-1-yl]-5-carbamoyloxy-3-methoxy-6-methyloxan-4-yl] acetate
xref: CHEMBL2205317
approved: f
ligand name: kibdelomycin A
type: NaturalProductLigand

rancinamycin IA
canonical SMILES: O=CC1=CC(O)C(C(C1OC(=O)C(C)C)O)O
isomeric SMILES: O=CC1=CC(O)C(C(C1OC(=O)C(C)C)O)O
in ch i key: TWOYHFIJNHPEEO-UHFFFAOYSA-N
in ch i: InChI=1S/C11H16O6/c1-5(2)11(16)17-10-6(4-12)3-7(13)8(14)9(10)15/h3-5,7-10,13-15H,1-2H3
comment: Rancinamycin IA is a lincomycin antibacterial that is produced by S. lincolnensis.
iupac name: (2-formyl-4,5,6-trihydroxycyclohex-2-en-1-yl) 2-methylpropanoate
synonym: U-22583
synonym: U22583
synonym: Rancomycin 1
approved: f
ligand name: rancinamycin IA
type: NaturalProductLigand

mersacidin
in ch i key: JSWKNDSDVHJUKY-CYGWNLPQSA-N
comment: Mersacidin is a type-B lantibacterial that is produced by Bacillus sp. HIL Y-85,54728. It is active in vivo against methicillin-resistant Staphylococcus aureus (MRSA) <Reference id=39637/>.
iupac name: 3-[(4S,7S,8S,11R,14S,17E,20S,26S)-7-[[(3S,6S,7S,10R,13S,28S)-6-[[(2S)-2-[[(2S,3S,6R)-6-amino-2-methyl-5-oxo-1,4-thiazepane-3-carbonyl]amino]-3-phenylpropanoyl]amino]-7-methyl-3-(2-methylpropyl)-2,5,12,15,18,21,24,27-octaoxo-13-propan-2-yl-8-thia-1,4,11,14,17,20,23,26-octazabicyclo[26.3.0]hentriacontane-10-carbonyl]amino]-14-[(2R)-butan-2-yl]-8,20-dimethyl-23-methylidene-4-(2-methylpropyl)-3,6,12,15,21,24,27-heptaoxo-9,19-dithia-2,5,13,16,22,25,28-heptazabicyclo[9.9.8]octacos-17-en-26-yl]propanoic acid
synonym: M87-1551
synonym: M87 1551
approved: f
ligand name: mersacidin
type: NaturalProductLigand

TP-271
in ch i key: VIWUYPVRNWIKLS-HMFHYXQTSA-N
comment: TP-271 is a fully synthetic fluorocycline antibacterial. It has activity against pathogens that cause respiratory tract infections, including complicated community-acquired bacterial pneumonia <Reference id=39636/>.
iupac name: (2S)-N-[(5aR,6aS,7S,10aR)-9-carbamoyl-7-(dimethylamino)-4-fluoro-1,10,10a,12-tetrahydroxy-8,11-dioxo-5a,6,6a,7-tetrahydro-5H-tetracen-2-yl]-1-methylpyrrolidine-2-carboxamide
xref: CHEMBL2057236
synonym: TP271
approved: f
ligand name: TP-271
type: SyntheticOrganicLigand

verdamicin
in ch i key: XUSXOPRDIDWMFO-URTZJOLISA-N
in ch i: InChI=1S/C20H39N5O7/c1-8(21)12-5-4-9(22)18(30-12)31-15-10(23)6-11(24)16(13(15)26)32-19-14(27)17(25-3)20(2,28)7-29-19/h5,8-11,13-19,25-28H,4,6-7,21-24H2,1-3H3/t8?,9-,10-,11+,13-,14+,15+,16-,17+,18-,19+,20-/m0/s1
comment: Verdamicin is an aminoglycoside antibacterial produced by Micromonospora grisea <Reference id=39630/>.
iupac name: (2R,3R,4R,5R)-2-[(1S,2S,3R,4S,6R)-4,6-diamino-3-[[(2R,3S)-3-amino-6-(1-aminoethyl)-3,4-dihydro-2H-pyran-2-yl]oxy]-2-hydroxycyclohexyl]oxy-5-methyl-4-(methylamino)oxane-3,5-diol
xref: CHEMBL1276546
synonym: 6'-C-Methylsisomicin
approved: f
ligand name: verdamicin
type: NaturalProductLigand

napsamycin D
in ch i key: AZGANZVUWUCOGH-XHPQRKPJSA-N
in ch i: InChI=1S/C40H52N8O12S/c1-20-27-9-8-25(50)16-23(27)17-29(42-20)36(55)47(3)21(2)33(35(54)41-19-26-18-31(51)37(60-26)48-12-10-32(52)45-40(48)59)46-34(53)28(11-13-61-4)43-39(58)44-30(38(56)57)15-22-6-5-7-24(49)14-22/h5-9,14,16,19-21,28-31,33,37,42,49-51H,10-13,15,17-18H2,1-4H3,(H,41,54)(H,46,53)(H,56,57)(H2,43,44,58)(H,45,52,59)/b26-19-
comment: Napsamycin D and <Ligand id=11008/> are uridylpeptide antibacterials, sharing a common structural scaffold with the mureidomycins and pacidamycins. Originally isolated from Streptomyces sp. HIL Y-82,11372, napsamycins have potent activity against Pseudomonas species but not against other Gram-negative or Gram-positive bacteria <Reference id=39629/>.
iupac name: 2-[[1-[[1-[[(Z)-[5-(2,4-dioxo-1,3-diazinan-1-yl)-4-hydroxyoxolan-2-ylidene]methyl]amino]-3-[(6-hydroxy-1-methyl1,2,3,4-tetrahydroisoquinoline-3-carbonyl)-methylamino]-1-oxobutan-2-yl]amino]-4-methylsulfanyl-1-oxobutan-2-yl]carbamoylamino]-3-(3-hydroxyphenyl)propanoic acid
approved: f
ligand name: napsamycin D
type: NaturalProductLigand

napsamycin C
in ch i key: MFEPAAMYDYMBSN-XHPQRKPJSA-N
in ch i: InChI=1S/C39H50N8O12S/c1-20(46(2)35(54)28-16-23-15-25(49)8-7-22(23)18-40-28)32(34(53)41-19-26-17-30(50)36(59-26)47-11-9-31(51)44-39(47)58)45-33(52)27(10-12-60-3)42-38(57)43-29(37(55)56)14-21-5-4-6-24(48)13-21/h4-8,13,15,19-20,27-30,32,36,40,48-50H,9-12,14,16-18H2,1-3H3,(H,41,53)(H,45,52)(H,55,56)(H2,42,43,57)(H,44,51,58)/b26-19-
comment: Napsamycin C and <Ligand id=11009/> are uridylpeptide antibacterials, sharing a common structural scaffold with the mureidomycins and pacidamycins. Originally isolated from Streptomyces sp. HIL Y-82,11372, napsamycins have potent activity against Pseudomonas species but not against other Gram-negative or Gram-positive bacteria <Reference id=39629/>.
iupac name: 2-[[1-[[1-[[(Z)-[5-(2,4-dioxo-1,3-diazinan-1-yl)-4-hydroxyoxolan-2-ylidene]methyl]amino]-3-[(6-hydroxy1,2,3,4-tetrahydroisoquinoline-3-carbonyl)-methylamino]-1-oxobutan-2-yl]amino]-4-methylsulfanyl-1-oxobutan-2-yl]carbamoylamino]-3-(3-hydroxyphenyl)propanoic acid
approved: f
ligand name: napsamycin C
type: NaturalProductLigand

ranbezolid
in ch i key: PWHNTOQANLCTHN-KRWDZBQOSA-N
in ch i: InChI=1S/C21H24FN5O6/c1-14(28)23-11-17-13-26(21(29)33-17)15-2-4-19(18(22)10-15)25-8-6-24(7-9-25)12-16-3-5-20(32-16)27(30)31/h2-5,10,17H,6-9,11-13H2,1H3,(H,23,28)/t17-/m0/s1
comment: Ranbezolid is an oxazolidinone class antibacterial with potent activity against a broad-spectrum of Gram-positive bacterial strains, including methicillin-resistant Staphylococcus aureus (MRSA) <Reference id=39621/>.
iupac name: N-[[(5S)-3-[3-fluoro-4-[4-[(5-nitrofuran-2-yl)methyl]piperazin-1-yl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide
xref: CHEMBL251384
synonym: RBx 7644
synonym: RBx7644
synonym: RBX-7644
approved: f
ligand name: ranbezolid
type: SyntheticOrganicLigand

RP60556A
in ch i key: YYHFVZLNDMSUBV-UHFFFAOYSA-N
in ch i: InChI=1S/C24H20F2N4O3/c1-28-13-18(24(32)33)22(31)17-10-14-11-19(26)21(12-20(14)27-23(17)28)30-8-6-29(7-9-30)16-4-2-15(25)3-5-16/h2-5,10-13H,6-9H2,1H3,(H,32,33)
comment: RP60556A is the most potent compound from the benzo[b]naphthyridones, a series of antibacterial compounds active against Gram-positive bacteria including methicillin-resistant Staphylococcus aureus (MRSA) <Reference id=39620/>. It was being developed as a topical treatment by Sanofi-Aventis but has been discontinued.
iupac name: 7-fluoro-8-[4-(4-fluorophenyl)piperazin-1-yl]-1-methyl-4-oxopyrido[6,5-b]quinoline-3-carboxylic acid
xref: CHEMBL1183217
approved: f
ligand name: RP60556A
type: SyntheticOrganicLigand

ω-Hydroxyemodin
in ch i key: YQHZABGPIPECSQ-UHFFFAOYSA-N
in ch i: InChI=1S/C15H10O6/c16-5-6-1-8-12(10(18)2-6)15(21)13-9(14(8)20)3-7(17)4-11(13)19/h1-4,16-19H,5H2
comment: ω-Hydroxyemodin is a polyhydroxyanthraquinone isolated from Penicillium restrictum. It has been investigated as an alternative or adjunctive to conventional antibacterials in the treatment of antibacterial-resistant infections, including invasive skin and soft tissue infections (SSTIs) caused by Staphylococcus aureus <Reference id=39618/>.
iupac name: 1,3,8-trihydroxy-6-(hydroxymethyl)anthracene-9,10-dione
xref: CHEMBL290932
synonym: omega-Hydroxyemodin
synonym: Citreorosein
approved: f
ligand name: ω-Hydroxyemodin
type: NaturalProductLigand

BAL30072
canonical SMILES: O=C1[C@@H](NC(=O)/C(=N/OCc2cc(=O)c(cn2O)O)/c2csc(n2)N)C(N1OS(=O)(=O)O)(C)C
isomeric SMILES: O=C1[C@@H](NC(=O)/C(=N/OCc2cc(=O)c(cn2O)O)/c2csc(n2)N)C(N1OS(=O)(=O)O)(C)C
in ch i key: KLFSEZJCLYBFKQ-WXYNYTDUSA-N
comment: BAL30072 is a monosulfactam antibacterial with Gram-negative activity <Reference id=39615/><Reference id=39616/>.
iupac name: [(3S)-3-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-[(1,5-dihydroxy-4-oxopyridin-2-yl)methoxyimino]acetyl]amino]-2,2-dimethyl-4-oxoazetidin-1-yl] hydrogen sulfate
xref: CHEMBL1256967
synonym: BAL-30072
approved: f
ligand name: BAL30072
type: SyntheticOrganicLigand

CB-182804
in ch i key: OINMSSZOBLWDTB-SHGLBBHXSA-N
comment: CB-182804 is a polymixin B analogue. It has activity against Gram-positive bacteria <Reference id=39614/>.
synonym: CB182804
synonym: CB-182,804
approved: f
ligand name: CB-182804
type: PeptideLigand

clemizole
canonical SMILES: Clc1ccc(cc1)Cn1c(CN2CCCC2)nc2c1cccc2
isomeric SMILES: Clc1ccc(cc1)Cn1c(CN2CCCC2)nc2c1cccc2
in ch i key: CJXAEXPPLWQRFR-UHFFFAOYSA-N
in ch i: InChI=1S/C19H20ClN3/c20-16-9-7-15(8-10-16)13-23-18-6-2-1-5-17(18)21-19(23)14-22-11-3-4-12-22/h1-2,5-10H,3-4,11-14H2
comment: Clemizole is principally known as an antagonist of the histamine H1 receptor. It has subsequently been identified as a transient receptor potential channel blocker with activity at the TRPC5 cation channel <Reference id=37281/>.
iupac name: 1-[(4-chlorophenyl)methyl]-2-(pyrrolidin-1-ylmethyl)benzimidazole
xref: CHEMBL1407943
approved: f
ligand name: clemizole
type: SyntheticOrganicLigand

cationomycin
in ch i key: SGLQOFJJLQBZBE-MSFHLGAUSA-N
in ch i: InChI=1S/C45H70O15/c1-13-32(48)41(7)19-24(4)37(59-41)31-15-23(3)38(55-31)44(10)34(54-12)18-35(58-44)43(9)25(5)20-45(60-43)21-29(47)26(6)30(57-45)17-33(42(8,52)40(50)51)56-39(49)36-22(2)14-27(53-11)16-28(36)46/h14,16,23-26,29-35,37-38,46-48,52H,13,15,17-21H2,1-12H3,(H,50,51)/t23-,24-,25?,26?,29?,30?,31+,32-,33?,34-,35?,37-,38+,41-,42?,43?,44-,45?/m0/s1
comment: Cationomycin is a polyether, ionophore antibacterial that is produced by Actinomadura azurea sp. nov. <Reference id=39612/><Reference id=39613/>. It has Gram-positive activity.
iupac name: 2-hydroxy-4-[7-hydroxy-2-[(4S,5S)-5-[(2R,3S,5R)-5-[(2S,3S,5S)-5-[(1S)-1-hydroxypropyl]-3,5-dimethyloxolan-2-yl]-3-methyloxolan-2-yl]-4-methoxy-5-methyloxolan-2-yl]-2,3,8-trimethyl-1,10-dioxaspiro[4.5]decan-9-yl]-3-(2-hydroxy-4-methoxy-6-methylbenzoyl)oxy-2-methylbutanoic acid
synonym: LS52659
synonym: BRN6263205
synonym: BRN-6263205
synonym: LS-52659
approved: f
ligand name: cationomycin
type: NaturalProductLigand

amphetamine
canonical SMILES: CC(Cc1ccccc1)N
isomeric SMILES: CC(Cc1ccccc1)N
in ch i key: KWTSXDURSIMDCE-UHFFFAOYSA-N
in ch i: InChI=1S/C9H13N/c1-8(10)7-9-5-3-2-4-6-9/h2-6,8H,7,10H2,1H3
comment: Amphetamine is a central nervous system stimulant and an appetite suppressant. Amphetamine can activate carbonic anhydrases, and is most potent at the CA5A and CA7 isoforms (KA values 810 and 910 nM respectively) <Reference id=38027/>.
iupac name: 1-phenylpropan-2-amine
xref: CHEMBL405
synonym: (±)-amphetamine
synonym: DL-amphetamine
synonym: Actedron
synonym: Adipan
synonym: Allodene
synonym: Anorexide
synonym: Anorexine
synonym: Benzebar
synonym: Benzedrine
synonym: Benzolone
synonym: Dexampex
synonym: Elastonon
synonym: Fenamin
synonym: Ferndex
synonym: Finam
synonym: Isoamycin
synonym: Isoamyne
synonym: Isomyn
synonym: Mecodrin
synonym: Methampex
synonym: Norephedrane
synonym: Novydrine
synonym: Oktedrin
synonym: Ortedrine
synonym: Paredrine
synonym: Percomon
synonym: Phenamine
synonym: Phenedrine
synonym: Profamina
synonym: Propisamine
synonym: Psychedrine
synonym: Raphetamine
synonym: Rhinalator
synonym: Simpatedrin
synonym: Simpatina
synonym: Sympamin
synonym: Sympamine
synonym: Sympatedrine
synonym: Weckamine
synonym: Amphetamine Sulfate®
approved: t
ligand name: amphetamine
type: SyntheticOrganicLigand

BC-3205
in ch i key: AFYOQRIZFPJUAR-UBTCORFISA-N
in ch i: InChI=1S/C32H52N2O5S/c1-8-30(6)16-24(31(7)20(4)11-13-32(21(5)28(30)37)14-12-23(35)27(31)32)39-25(36)18-40-22-10-9-15-34(17-22)29(38)26(33)19(2)3/h8,19-22,24,26-28,37H,1,9-18,33H2,2-7H3/t20-,21+,22?,24-,26-,27+,28+,30-,31+,32+/m1/s1
comment: BC-3205 is pleuromutilin-derived antibacterial with Gram-negative activity <Reference id=39602/><Reference id=39604/>.
approved: f
ligand name: BC-3205
type: SyntheticOrganicLigand

MGB-BP-3
in ch i key: OEKXCVYZBVOWBR-BQYQJAHWSA-N
in ch i: InChI=1S/C36H37N7O4/c1-41-24-30(20-32(41)35(45)37-13-14-43-15-17-47-18-16-43)40-36(46)33-21-29(23-42(33)2)39-34(44)27-11-9-25(10-12-27)7-8-26-19-28-5-3-4-6-31(28)38-22-26/h3-12,19-24H,13-18H2,1-2H3,(H,37,45)(H,39,44)(H,40,46)/b8-7+
comment: MGB-BP-3 is an antibacterial that inhiits bacterial DNA replication <Reference id=39600/>.
iupac name: 1-methyl-N-[1-methyl-5-(2-morpholin-4-ylethylcarbamoyl)pyrrol-3-yl]-4-[[4-[(E)-2-quinolin-3-ylethenyl]benzoyl]amino]pyrrole-2-carboxamide
xref: CHEMBL236345
synonym: MGB-BP3
synonym: compound 50 [PMID: 17960927]
approved: f
ligand name: MGB-BP-3
type: SyntheticOrganicLigand

BLI-489 free acid
canonical SMILES: O=C1/C(=C/c2cn3c(n2)COCC3)/[C@@H]2N1C(=CS2)C(=O)O
isomeric SMILES: O=C1/C(=C/c2cn3c(n2)COCC3)/[C@@H]2N1C(=CS2)C(=O)O
in ch i key: DMEYZPJEFHGESJ-CPWLGJMPSA-N
in ch i: InChI=1S/C13H11N3O4S/c17-11-8(12-16(11)9(6-21-12)13(18)19)3-7-4-15-1-2-20-5-10(15)14-7/h3-4,6,12H,1-2,5H2,(H,18,19)/b8-3-/t12-/m1/s1
comment: BLI-489 is a carbapenem β-lactamase inhibitor <Reference id=39599/>.
iupac name: (5R,6Z)-6-(6,8-dihydro-5H-imidazo[2,1-c][1,4]oxazin-2-ylmethylidene)-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
xref: CHEMBL4302412
synonym: BLI489
approved: f
ligand name: BLI-489 free acid
type: SyntheticOrganicLigand

etheromycin
in ch i key: DIKYHBWGIUNGIW-UHFFFAOYSA-N
in ch i: InChI=1S/C48H82O16/c1-24(41-45(10,61-37-18-16-31(54-12)30(7)57-37)40(49)28(5)48(53,63-41)29(6)42(50)51)33-23-34(55-13)26(3)47(59-33)22-21-44(9,64-47)36-19-20-43(8,60-36)35-17-15-32(58-35)39-25(2)38(56-14)27(4)46(11,52)62-39/h24-41,49,52-53H,15-23H2,1-14H3,(H,50,51)
comment: Etheromycin is an ionophore antibacterial with Gram-positive activity. It appears to be selective for monovalent cations <Reference id=39598/>. See also etheromycin sodium (PubChem CID 23667550).
iupac name: 2-[2,4-dihydroxy-6-[1-[2-[5-[5-(6-hydroxy-4-methoxy-3,5,6-trimethyloxan-2-yl)oxolan-2-yl]-5-methyloxolan-2-yl]-7-methoxy-2,6-dimethyl-1,10-dioxaspiro[4.5]decan-9-yl]ethyl]-5-(5-methoxy-6-methyloxan-2-yl)oxy-3,5-dimethyloxan-2-yl]propanoic acid
synonym: CP‐38 295
approved: f
ligand name: etheromycin
type: SyntheticOrganicLigand

BRL-42715
canonical SMILES: O=C1/C(=C/c2c[nH]nn2)/[C@@H]2N1C(=CS2)C(=O)O
isomeric SMILES: O=C1/C(=C/c2c[nH]nn2)/[C@@H]2N1C(=CS2)C(=O)O
in ch i key: WFUNKYVUHIZWEW-VRFQNRHZSA-N
in ch i: InChI=1S/C9H6N4O3S/c14-7-5(1-4-2-10-12-11-4)8-13(7)6(3-17-8)9(15)16/h1-3,8H,(H,15,16)(H,10,11,12)/b5-1+/t8-/m1/s1
comment: Strictly BRL-42715 is the sodium salt (PubChem CID 6436245); CAS number 102209-75-6) of the parent molecule provided here. BRL-42715 is a β-lactamase-inhibiting penem antibacterial <Reference id=39592/><Reference id=39594/><Reference id=39595/>.
iupac name: (5R,6E)-6-[(1-methyltriazol-4-yl)methylidene]-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
synonym: LS-187554
synonym: LS-186900 (sodium salt)
synonym: C6-(N1-Methyl-1,2,3-trazolylmethylene)penem
approved: f
ligand name: BRL-42715
type: SyntheticOrganicLigand

dihydroxybenzofuran
canonical SMILES: Oc1c(O)oc2c1cccc2
isomeric SMILES: Oc1c(O)oc2c1cccc2
in ch i key: DNDWXJDUTDZBNV-UHFFFAOYSA-N
in ch i: InChI=1S/C8H6O3/c9-7-5-3-1-2-4-6(5)11-8(7)10/h1-4,9-10H
comment: Dihydroxybenzofuran has antibacterial activity against Gram-positive bacteria.
iupac name: 1-benzofuran-2,3-diol
synonym: 2,3-Benzofurandiol
approved: f
ligand name: dihydroxybenzofuran
type: SyntheticOrganicLigand

CRS3123
in ch i key: NNTYBKTXMKBRFA-CQSZACIVSA-N
comment: CRS3123 is an orally bioative, diaryldiamine compound that inhibits bacterial methionyl-tRNA synthetases in Gram-positive bacteria <Reference id=39589/>. It has limited activity against normal anaerobic gut flora (e.g. Clostridium ramosum, bifidobacteria, lactobacilli of the Lactobacillus casei-rhamnosus-plantarum group) and Gram-negative anaerobes.
iupac name: 5-[3-[[(4R)-6,8-dibromo-3,4-dihydro-2H-chromen-4-yl]amino]propylamino]-4H-thieno[3,2-b]pyridin-7-one
xref: CHEMBL4297370
synonym: CRS-3123
synonym: REP-3123
synonym: REP3123
approved: f
ligand name: CRS3123
type: SyntheticOrganicLigand

NIK inhibitor 12f
in ch i key: KJMURTHIPWRIMC-UHFFFAOYSA-N
in ch i: InChI=1S/C23H22N6O2S/c1-23(30,22-25-8-13-32-22)6-4-16-2-3-19(29-9-11-31-12-10-29)18(14-16)28-21-17-5-7-24-20(17)26-15-27-21/h2-3,5,7-8,13-15,30H,9-12H2,1H3,(H2,24,26,27,28)
comment: Compound 12f is a orally bioavailable, selective inhibitor of NF-κB inducing kinase (NIK; MAP3K14) <Reference id=39516/>.
iupac name: 4-(3-((7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)-4-morpholinophenyl)-2-(thiazol-2-yl)but-3-yn-2-ol
approved: f
ligand name: NIK inhibitor 12f
type: SyntheticOrganicLigand

Thiazomycin A
in ch i key: LPGAAUZJQIRAAG-CAYKKMKNSA-N
comment: Thiazomycin A is a thiazolyl macrocyclic peptide antibacterial produced by Amycolatopsis fastidiosa <Reference id=39588/>. It is a potent Gram-positive antibacterial agent.
xref: CHEMBL500817
synonym: compound 6 [PMID: 18804380]
approved: f
ligand name: Thiazomycin A
type: SyntheticOrganicLigand

Enduracidin
in ch i key: QKXQEKZXVMLAMO-JDCCHMEXSA-N
comment: Enduracidin is an experimental antibacterial produced by a strain of Streptomyces fungicidicus found in soil <Reference id=39585/><Reference id=39586/>. It has potent antibacterial activity against Gram-positive bacteria.
iupac name: 4-[[41-(4-aminobutyl)-9,23-bis[(2-amino-4,5-dihydro-1H-imidazol-4-yl)methyl]-26-[3-(carbamoylamino)propyl]-14-(3,5-dichloro-4-hydroxyphenyl)-29,38-bis(1-hydroxyethyl)-17-(hydroxymethyl)-3,20,32,35,43-pentakis(4-hydroxyphenyl)-6,47-dimethyl-2,5,8,11,13,16,19,22,25,28,31,34,37,40,42,45-hexadecaoxo-1-oxa-4,7,10,12,15,18,21,24,27,30,33,36,39,41,44-pentadecazacycloheptatetracont-46-yl]amino]-3-[[(2E,4E)-10-methyldodeca-2,4-dienoyl]amino]-4-oxobutanoic acid
approved: f
ligand name: Enduracidin
type: SyntheticOrganicLigand

BAS-118
in ch i key: VQVCFYIDCWPSNE-UHFFFAOYSA-N
in ch i: InChI=1S/C20H18N2O2/c1-21-20(24)17-7-4-8-18(13-17)22-19(23)12-14-9-10-15-5-2-3-6-16(15)11-14/h2-11,13H,12H2,1H3,(H,21,24)(H,22,23)
comment: BAS-118 is an experimental benzamide derivative with antibacterial activity <Reference id=39562/>.
iupac name: N-methyl-3-[(2-naphthalen-2-ylacetyl)amino]benzamide
xref: CHEMBL141566
synonym: compound 7n [PMID: 11728192]
synonym: BAS118
synonym: BAS 118
approved: f
ligand name: BAS-118
type: SyntheticOrganicLigand

cyclothialidine
in ch i key: HMHQWJDFNVJCHA-ZPGBQQFCSA-N
in ch i: InChI=1S/C26H35N5O12S/c1-10-17(34)5-18(35)12-8-44-9-15(22(37)28-11(2)25(40)41)30-21(36)14(7-43-26(42)19(10)12)29-23(38)20-16(33)3-4-31(20)24(39)13(27)6-32/h5,11,13-16,20,32-35H,3-4,6-9,27H2,1-2H3,(H,28,37)(H,29,38)(H,30,36)(H,40,41)/t11-,13?,14-,15-,16+,20-/m0/s1
comment: Cyclothialidine is a potent DNA gyrase inhibitor, isolated from Streptomyces filipinensis following microbial broth screening <Reference id=39591/>. It belongs to a novel class of antibacterial compounds, containing a unique 12-membered lactone ring that is partly integrated into a pentapeptide chain, that exhibit broad-spectrum in vitro activity against Gram-positive bacteria. Further development of cyclothialidine has been precluded due to low growth-inhibitory activity against intact bacterial cells but analogues with improved in vivo efficacy have been synthesized <Reference id=39605/>.
iupac name: (2S)-2-[[(5S,8R)-5-[[(2S,3R)-1-(2-amino-3-hydroxypropanoyl)-3-hydroxypyrrolidine-2-carbonyl]amino]-13,15-dihydroxy-16-methyl-2,6-dioxo3-oxa-10-thia-7-azabicyclo[10.4.0]hexadeca-1(16),12,14-triene-8-carbonyl]amino]propanoic acid
xref: CHEMBL4286501
synonym: Ro 09-1437
approved: f
ligand name: cyclothialidine
type: NaturalProductLigand

SRI-20920
in ch i key: SZAZJRVSIHGLCG-UHFFFAOYSA-N
in ch i: InChI=1S/C20H26N6O2/c1-4-8-28-16-7-6-14(27-5-2)9-15(16)23-10-13-11-24-19-17(12(13)3)18(21)25-20(22)26-19/h6-7,9,11,23H,4-5,8,10H2,1-3H3,(H4,21,22,24,25,26)
comment: SRI-20920 is a Mycobacterium avium dihydrofolate reductase (DHFR) inhibitor, anti-folate antibacterial <Reference id=39583/>.
iupac name: 6-[(5-ethoxy-2-propoxyanilino)methyl]-5-methylpyrido[2,3-d]pyrimidine-2,4-diamine
synonym: SRI20920
synonym: SRI 20920
approved: f
ligand name: SRI-20920
type: SyntheticOrganicLigand

SRI-20864
in ch i key: CRZVJULBIPRHRY-UHFFFAOYSA-N
in ch i: InChI=1S/C18H22N6O2/c1-4-26-12-5-6-14(25-3)13(7-12)21-8-11-9-22-17-15(10(11)2)16(19)23-18(20)24-17/h5-7,9,21H,4,8H2,1-3H3,(H4,19,20,22,23,24)
comment: SRI-20864 is an experimental antibacterial compound. It acts as an inhibitor of bacterial dihydrofolate reductase (DHFR; an antifolate antibacterial), and was generated in a programme that also included SRI-8858 <Reference id=39582/>. These compounds were developed to treat trimethoprim-resistant Mycobacterium avium complex (MAC).
iupac name: 6-[(5-ethoxy-2-methoxyanilino)methyl]-5-methylpyrido[2,3-d]pyrimidine-2,4-diamine
synonym: SRI20864
approved: f
ligand name: SRI-20864
type: SyntheticOrganicLigand

DS-2969b
in ch i key: RFKLYBAHWNXIDR-MNOVXSKESA-N
comment: DS-2969b is an orally active antimicrobial compound that acts as a novel DNA gyrase B inhibitor <Reference id=39579/>. It has useful activity against Clostridium difficile <Reference id=39580/>
xref: CHEMBL4067729
synonym: DS-2969
synonym: DS 11960558 (DS-2969b prodrug)
synonym: example 2 [WO2017/056012A1]
approved: f
ligand name: DS-2969b
type: SyntheticOrganicLigand

CG-400549
canonical SMILES: Nc1cccc(c1C)Cn1ccc(cc1=O)OCCc1cccs1
isomeric SMILES: Nc1cccc(c1C)Cn1ccc(cc1=O)OCCc1cccs1
in ch i key: YCLREGRRHGLOAK-UHFFFAOYSA-N
in ch i: InChI=1S/C19H20N2O2S/c1-14-15(4-2-6-18(14)20)13-21-9-7-16(12-19(21)22)23-10-8-17-5-3-11-24-17/h2-7,9,11-12H,8,10,13,20H2,1H3
comment: CG400549 is an antibacterial compound that functions by inhibiting bacterial enoyl-ACP reductase (FabI) <Reference id=39577/>. It has no activity against Gram-positive bacteria.
iupac name: 1-[(3-amino-2-methylphenyl)methyl]-4-(2-thiophen-2-ylethoxy)pyridin-2-one
xref: CHEMBL488937
synonym: CG400549
synonym: CG 400549
approved: f
ligand name: CG-400549
type: SyntheticOrganicLigand

AN0128
in ch i key: ZTLSOLUCMQEGEA-UHFFFAOYSA-N
comment: AN0128 is a borinic acid picolinate ester with anti-bacterial and anti-inflammatory activities <Reference id=39575/>. It was proposed as a treatment for dermatological conditions <Reference id=39575/> and as a component for anti-bacterial toothpaste <Reference id=39576/>.
iupac name: bis(3-chloro-4-methylphenyl)boranyl 3-hydroxypyridine-2-carboxylate
xref: CHEMBL219629
synonym: AN-0128
synonym: AN 0128
synonym: compound 2g [PMID: 16997550]
approved: f
ligand name: AN0128
type: SyntheticOrganicLigand

DC-159a
in ch i key: CWRHFWJFDKNNCM-WCQYABFASA-N
in ch i: InChI=1S/C20H20F2N3O4/c1-29-18-15-9(17(26)10(19(27)28)6-25(15)13-5-11(13)21)4-12(22)16(18)24-7-14(23)20(8-24)2-3-20/h4,6,11,13H,2-3,5,7-8,23H2,1H3,(H,27,28)/t11-,13+/m0/s1
comment: DC-159a is a fluoroquinolone antibacterial <Reference id=39574/>.
iupac name: 7-[(7S)-7-amino-7-methyl-5-azaspiro[2.4]heptan-5-yl]-6-fluoro-1-[(1R,2S)-2-fluorocyclopropyl]-8-methoxy-4-oxoquinoline-3-carboxylic acid
xref: CHEMBL1197225
approved: f
ligand name: DC-159a
type: SyntheticOrganicLigand

BAL19403
in ch i key: HTEVRIKKCSOLOA-AKGQNOEZSA-N
in ch i: InChI=1S/C48H76N4O13S/c1-15-33-48(10)35(39(44(57)65-48)66-20-19-52-24-50-31-17-16-18-49-42(31)52)27(4)36(53)25(2)22-47(9,59-14)41(64-45-37(54)32(51(11)12)21-26(3)60-45)28(5)38(29(6)43(56)62-33)63-34-23-46(8,58-13)40(55)30(7)61-34/h16-18,24-30,32-35,37-41,45,54-55H,15,19-23H2,1-14H3/t25-,26-,27-,28+,29-,30+,32+,33-,34+,35+,37-,38+,39+,40+,41-,45+,46-,47-,48-/m1/s1
comment: BAL19403 is an experimental macrolide antibacterial <Reference id=39573/>. It has in vitro activity against propionibacteria, including erythromycin- and clindamycin-resistant propionibacteria, and exhibits some anti-inflammatory activity. It was proposed as a topical agent for mild to moderate inflammatory acne vulgaris.
iupac name: (1S,2R,5R,6S,7S,8R,9R,11R,13R,14R,15S)-8-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-2-ethyl-6-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-15-(2-imidazo[4,5-b]pyridin-3-ylethylsulfanyl)-9-methoxy-1,5,7,9,11,13-hexamethyl-3,17-dioxabicyclo[12.3.0]heptadecane-4,12,16-trione
xref: CHEMBL405863
synonym: BAL 19403
synonym: BAL-19403
approved: f
ligand name: BAL19403
type: SyntheticOrganicLigand

L-708365
in ch i key: ZZRQNCPNJLVUMK-UZSBJOJWSA-N
in ch i: InChI=1S/C40H74N2O12/c1-15-17-42-21-22(3)33(44)40(11,48)29(16-2)52-36(46)26(7)32(53-30-20-39(10,49-14)34(45)27(8)51-30)25(6)35(38(9,47)19-23(42)4)54-37-31(43)28(41(12)13)18-24(5)50-37/h15,22-35,37,43-45,47-48H,1,16-21H2,2-14H3/t22-,23+,24+,25-,26+,27-,28-,29+,30-,31+,32-,33+,34-,35+,37-,38+,39+,40+/m0/s1
comment: L-708365 is an azalide derivative of erythromycin <Reference id=39572/>. It has improved acid stability compared to erythromycin, azithromycin and clarithromycin.
iupac name: (2R,3S,4R,5S,8R,10R,11R,12S,13S,14R)-11-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-2-ethyl-3,4,10-trihydroxy-13-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-3,5,8,10,12,14-hexamethyl-7-prop-2-enyl-1-oxa-7-azacyclopentadecan-15-one
synonym: L-708,365
synonym: L 708,365
synonym: L 708365
approved: f
ligand name: L-708365
type: SyntheticOrganicLigand

feldamycin
in ch i key: LUOBEJSTJAVJPL-UHFFFAOYSA-N
in ch i: InChI=1S/C17H25N7O5/c1-9(23-13(16(26)27)4-11-6-20-8-22-11)14(17(28)29)24-15(25)12(18-2)3-10-5-19-7-21-10/h5-9,12-14,18,23H,3-4H2,1-2H3,(H,19,21)(H,20,22)(H,24,25)(H,26,27)(H,28,29)
comment: Feldamycin is a naturally occurring antibacterial agent produced by Streptomyces ficellus <Reference id=39570/><Reference id=39568/><Reference id=39569/>. Its in vitro antibacterial activity was not reproduced in rodent infection models. Feldamycin can be made using synthetic chemistry <Reference id=39571/>.
iupac name: 3-[[1-carboxy-2-(1H-imidazol-5-yl)ethyl]amino]-2-[[3-(1H-imidazol-5-yl)-2-(methylamino)propanoyl]amino]butanoic acid
synonym: BMY 28565
synonym: BMY28565
synonym: BMY-28565
synonym: U-48266
approved: f
ligand name: feldamycin
type: NaturalProductLigand

Macquarimicin A
in ch i key: BYUKEFZLYIFNCB-MDRYBKLPSA-N
in ch i: InChI=1S/C19H22O5/c1-9-4-15-13(18(9)22)3-2-10-5-11(20)6-12-7-17(21)16(8-14(10)15)19(23)24-12/h2-3,8-15,20H,4-7H2,1H3/b16-8+/t9-,10-,11-,12-,13+,14+,15+/m1/s1
comment: Macquarimicin A was originally isolated as a microbial metabolite from Micromonospora chalcea <Reference id=39565/>. A synthetic pathway to generate the Macquarimicin A structure has subsequently been reported <Reference id=39566/>. It has some limited antibacterial activity, and has actvity as a neutral sphingomyelinase (N-SMase, sphingomyelin phosphodiesterase) inhibitor <Reference id=39567/>.
approved: f
ligand name: Macquarimicin A
type: SyntheticOrganicLigand

PNU-288034
in ch i key: HSGZLFWXBIVLBD-LBPRGKRZSA-N
comment: PNU-288034 is an experimental oxazolidinone compound with antimicrobial activity <Reference id=39564/>.
iupac name: N-[[(5S)-3-[4-(1,1-dioxo-1,4-thiazinan-4-yl)-3,5-difluorophenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide
xref: CHEMBL377788
synonym: compound 2 [PMID: 16644216]
synonym: PNU288034
approved: f
ligand name: PNU-288034
type: SyntheticOrganicLigand

meptazinol
canonical SMILES: CCC1(CCCCN(C1)C)c1cccc(c1)O
isomeric SMILES: CCC1(CCCCN(C1)C)c1cccc(c1)O
in ch i key: JLICHNCFTLFZJN-UHFFFAOYSA-N
in ch i: InChI=1S/C15H23NO/c1-3-15(9-4-5-10-16(2)12-15)13-7-6-8-14(17)11-13/h6-8,11,17H,3-5,9-10,12H2,1-2H3
comment: Meptazinol is an opioid receptor agonist, with analgesic action. The INN recprod for this drug shows that it is a mixture of enantiomers. We show the molecule without specified stereochemistry to represent the mixture.
iupac name: 3-(3-ethyl-1-methylazepan-3-yl)phenol
xref: CHEMBL314437
synonym: Meptid®
approved: t
ligand name: meptazinol
type: SyntheticOrganicLigand

Irresistin-16
in ch i key: CKQXMSDRDDHCOR-UHFFFAOYSA-N
in ch i: InChI=1S/C23H19N5/c24-22-21-18-12-13-28(20(18)11-10-19(21)26-23(25)27-22)14-15-6-8-17(9-7-15)16-4-2-1-3-5-16/h1-13H,14H2,(H4,24,25,26,27)
comment: Irresistin-16 is a derivative of <Ligand id=10971/>, that was designed to increase antibacterial potency <Reference id=39561/>.
iupac name: 7-[(4-phenylphenyl)methyl]pyrrolo[3,2-f]quinazoline-1,3-diamine
xref: CHEMBL587612
synonym: IRS-16
synonym: IRS16
approved: f
ligand name: Irresistin-16
type: SyntheticOrganicLigand

teixobactin
in ch i key: LMBFAGIMSUYTBN-MPZNNTNKSA-N
in ch i: InChI=1S/C58H95N15O15/c1-12-28(5)42(70-49(79)37(61-11)23-34-19-17-16-18-20-34)53(83)67-39(26-74)51(81)65-36(21-22-41(59)76)48(78)69-44(30(7)14-3)55(85)71-43(29(6)13-2)54(84)68-40(27-75)52(82)73-46-33(10)88-57(87)45(31(8)15-4)72-50(80)38(24-35-25-62-58(60)64-35)66-47(77)32(9)63-56(46)86/h16-20,28-33,35-40,42-46,61,74-75H,12-15,21-27H2,1-11H3,(H2,59,76)(H,63,86)(H,65,81)(H,66,77)(H,67,83)(H,68,84)(H,69,78)(H,70,79)(H,71,85)(H,72,80)(H,73,82)(H3,60,62,64)/t28-,29-,30-,31-,32-,33-,35-,36+,37+,38-,39-,40-,42-,43-,44+,45-,46+/m0/s1
comment: Teixobactin is a small natural peptide produced by soil-dwelling bacteria <Reference id=39559/><Reference id=39560/>. It blocks bacterial cell wall synthesis <Reference id=39558/>, but using a different mechanism to other cell wall inhibitor antibacterial drugs.
xref: CHEMBL3977597
synonym: N-[N-Methyl-D-Phe-Ile-Ser-D-Gln-D-aIle-Ile-Ser-]cyclo[D-Thr*-Ala-[3-(2-iminoimidazolidine-4beta-yl)-Ala-]-Ile-]
synonym: compound of formula II [WO2014089053A1]
approved: f
ligand name: teixobactin
type: NaturalProductLigand

SCH-79797
in ch i key: AVXQPEKZIGPIJW-UHFFFAOYSA-N
in ch i: InChI=1S/C23H25N5/c1-14(2)16-5-3-15(4-6-16)13-28-12-11-18-20(28)10-9-19-21(18)22(24)27-23(26-19)25-17-7-8-17/h3-6,9-12,14,17H,7-8,13H2,1-2H3,(H3,24,25,26,27)
comment: Potent, selective non-peptide PAR1 antagonist. Marketed as SCH-79797 dihydrochloride. Other biological activity: SCH-79797 has been reported to exhibit antibacterial activity against Gram-positive and -negative bacteria, including MRSA and other clinically significant bacterial pathogens, with a low frequency of resistance in vivo <Reference id=39561/>. The authors show that SCH-79797 targets both bacterial folate metabolism and membrane integrity to mediate its antibacterial effect.
iupac name: N'-cyclopropyl-7-[(4-propan-2-ylphenyl)methyl]pyrrolo[3,2-f]quinazoline-1,3-diamine
xref: CHEMBL63426
synonym: SCH79797
synonym: SCH 79797
approved: f
ligand name: SCH-79797
type: SyntheticOrganicLigand

Katanosin B
in ch i key: KQMKBWMQSNKASI-UHFFFAOYSA-N
in ch i: InChI=1S/C58H97N15O17/c1-12-30(10)39-53(85)71-40(31(11)75)52(84)64-24-38(76)69-42(45(78)47(60)79)55(87)68-37(25-74)57(89)90-46(32-17-14-13-15-18-32)43(73-51(83)36(23-28(6)7)66-48(80)33(59)21-26(2)3)56(88)72-41(44(77)29(8)9)54(86)67-35(22-27(4)5)50(82)65-34(49(81)70-39)19-16-20-63-58(61)62/h13-15,17-18,26-31,33-37,39-46,74-75,77-78H,12,16,19-25,59H2,1-11H3,(H2,60,79)(H,64,84)(H,65,82)(H,66,80)(H,67,86)(H,68,87)(H,69,76)(H,70,81)(H,71,85)(H,72,88)(H,73,83)(H4,61,62,63)
comment: Katanosins (lysobactins) are antibacterial compounds <Reference id=39556/>. They have been isolated from Cytophaga <Reference id=39551/> or the Gram-negative bacterium Lysobacter sp <Reference id=39552/>. Katanosin B is also known as lysobactin. This can now be chemically synthesised <Reference id=39553/><Reference id=39554/>. Katanosins target bacterial cell wall biosynthesis <Reference id=39555/> and they are potent against problematic Gram-positive hospital pathogens such as staphylococci and enterococci.
iupac name: 2-amino-N-[1-[[6-(2-amino-1-hydroxy-2-oxoethyl)-15-butan-2-yl-18-[3-(diaminomethylideneamino)propyl]-12-(1-hydroxyethyl)-3-(hydroxymethyl)-24-(1-hydroxy-2-methylpropyl)-21-(2-methylpropyl)-2,5,8,11,14,17,20,23,26-nonaoxo-28-phenyl-1-oxa-4,7,10,13,16,19,22,25-octazacyclooctacos-27-yl]amino]-4-methyl-1-oxopentan-2-yl]-4-methylpentanamide
synonym: Lysobactin
approved: f
ligand name: Katanosin B
type: NaturalProductLigand

lysinomicin
in ch i key: WTENXKAJCSHCNH-QJSCRMMJSA-N
in ch i: InChI=1S/C20H40N6O6/c1-25-15-17(29)18(14(24)16(28)19(15)30-2)32-20-12(6-5-11(9-22)31-20)26-13(27)8-10(23)4-3-7-21/h5,10,12,14-20,25,28-29H,3-4,6-9,21-24H2,1-2H3,(H,26,27)/t10-,12+,14-,15-,16-,17+,18+,19-,20+/m0/s1
comment: Lysinomicin is a broad-spectrum aminoglycoside antibacterial <Reference id=39550/> with Gram-negative and Gram-positive activities. It is particularly active against <Ligand id=2427/> resistant bacteria.
iupac name: (3S)-3,6-diamino-N-[(2S,3R)-2-[(1R,2S,3S,4S,5S,6R)-2-amino-3,6-dihydroxy-4-methoxy-5-(methylamino)cyclohexyl]oxy-6-(aminomethyl)-3,4-dihydro-2H-pyran-3-yl]hexanamide
approved: f
ligand name: lysinomicin
type: NaturalProductLigand

decaplanin
in ch i key: SJSZMXQSCZCGFO-UHFFFAOYSA-N
comment: Decaplanin is a glycopeptide antibacterial that was developed for Gram-positive activity <Reference id=39548/><Reference id=39549/>.
synonym: MM-47761
synonym: M 861410
synonym: M86-1410
approved: f
ligand name: decaplanin
type: SyntheticOrganicLigand

poststatin
in ch i key: UNPBSZUDTFBULK-CZCKBYKRSA-N
comment: Poststatin is produced by Streptomyces viridochromogenes MH534-30F3 <Reference id=39546/>. It acts as an inhibitor of prolyl endopeptidase.
iupac name: (2S)-2-[[(2R)-2-[[(3S)-3-amino-2-oxopentanoyl]amino]-4-methylpentanoyl]-[(2S,6S)-2,6-diamino-3,7-dimethyl-5-oxooctanoyl]amino]-3-methylbutanoic acid
synonym: L-Val-L-Val-3-amino-2-oxo-valeryl-D-Leu-L-Val
approved: f
ligand name: poststatin
type: NaturalProductLigand

Ferrimycin A1
in ch i key: GYDPFTRJZUGPNF-UHFFFAOYSA-N
in ch i: InChI=1S/C40H63N10O14.Fe/c1-39(40(60,25-51)35(41)34(36(42)64-2)38(59)47-39)46-28-22-27(23-29(53)24-28)37(58)45-18-8-5-11-21-50(63)33(57)15-13-31(55)44-17-7-4-10-20-49(62)32(56)14-12-30(54)43-16-6-3-9-19-48(61)26-52;/h22-24,26,34-35,42,46,51,53,60H,3-21,25,41H2,1-2H3,(H,43,54)(H,44,55)(H,45,58)(H,47,59);/q-3;+3
comment: Ferrimycin A is an iron-containing sideromycin antibacterial <Reference id=39545/>. It is produced by soil-dwelling Streptomyces galilaeus.
iupac name: iron(3+);methyl 6-[3-[5-[[4-[5-[[4-[5-[acetyl(oxido)amino]pentylamino]-4-oxobutanoyl]-oxidoamino]pentylamino]-4-oxobutanoyl]-oxidoamino]pentylcarbamoyl]-5-hydroxyanilino]-4-amino-5-hydroxy-5-(hydroxymethyl)-6-methyl-2-oxopiperidine-3-carboximidate
approved: f
ligand name: Ferrimycin A1
type: NaturalProductLigand

ficellomycin
in ch i key: DGIHWRUPUISVIZ-UHFFFAOYSA-N
in ch i: InChI=1S/C13H24N6O3/c1-5(2)9(14)11(20)18-10(12(21)22)7-3-6(17-13(15)16)8-4-19(7)8/h5-10H,3-4,14H2,1-2H3,(H,18,20)(H,21,22)(H4,15,16,17)
comment: Ficellomycin is an antibacterial produced by Streptomyces ficellus <Reference id=39544/>. It has Gram-positive activity.
iupac name: 2-[(2-amino-3-methylbutanoyl)amino]-2-[4-(diaminomethylideneamino)-1-azabicyclo[3.1.0]hexan-2-yl]acetic acid
synonym: U 47929
synonym: U47929
synonym: U-47929
synonym: U-47,929
approved: f
ligand name: ficellomycin
type: NaturalProductLigand

Altromycin B
in ch i key: FAGGWQMBDCZCOI-UHFFFAOYSA-N
in ch i: InChI=1S/C47H59NO18/c1-18-34(50)27(58-9)16-30(62-18)65-42-20(3)61-28(17-45(42,5)48(7)8)22-12-13-23-31(37(22)53)38(54)32-24(36(23)52)14-25(33-26(49)15-29(64-40(32)33)46(6)21(4)66-46)47(57,44(56)60-11)43-39(55)41(59-10)35(51)19(2)63-43/h12-15,18-21,27-28,30,34-35,39,41-43,50-51,53,55,57H,16-17H2,1-11H3
comment: Altromycin B is a pluramycin-like, anthraquinone antitumour antibacterial that was developed for Gram-negative activity <Reference id=39542/><Reference id=39543/>. It was isolated from a soil-dwelling actinomycete, AB 1246E-26. As it is a DNA minor groove binder and DNA alkylator it is likely highly toxic.
iupac name: methyl 2-(3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl)-2-[10-[4-(dimethylamino)-5-(5-hydroxy-4-methoxy-6-methyloxan-2-yl)oxy-4,6-dimethyloxan-2-yl]-2-(2,3-dimethyloxiran-2-yl)-11-hydroxy-4,7,12-trioxonaphtho[2,3-h]chromen-5-yl]-2-hydroxyacetate
approved: f
ligand name: Altromycin B
type: NaturalProductLigand

CGP-31608
in ch i key: RXCNILVLOHRALM-UWBRJAPDSA-N
in ch i: InChI=1S/C9H12N2O4S/c1-3(12)5-7(13)11-6(9(14)15)4(2-10)16-8(5)11/h3,5,8,12H,2,10H2,1H3,(H,14,15)/t3-,5+,8-/m1/s1
comment: CGP 31608 is a semisynthetic penem derived antibacterial, with Gram-positive and Gram-negative activities <Reference id=39539/><Reference id=39540/><Reference id=39541/>.
iupac name: (5R,6S)-3-(aminomethyl)-6-[(1R)-1-hydroxyethyl]-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
xref: CHEMBL308425
synonym: CGP 31608
synonym: CGP31608
approved: f
ligand name: CGP-31608
type: SyntheticOrganicLigand

neopyrrolomycin
canonical SMILES: Clc1c(Cl)cc(c(c1Cl)n1ccc(c1Cl)Cl)O
isomeric SMILES: Clc1c(Cl)cc(c(c1Cl)n1ccc(c1Cl)Cl)O
in ch i key: VQUHAXJBUPCVDX-UHFFFAOYSA-N
in ch i: InChI=1S/C10H4Cl5NO/c11-4-1-2-16(10(4)15)9-6(17)3-5(12)7(13)8(9)14/h1-3,17H
comment: Neopyrrolomycin is a chlorinated phenylpyrrole antibacterial, with Gram-positive and Gram-negative activities that was isolated form a Streptomyces species <Reference id=39538/>.
iupac name: 3,4,5-trichloro-2-(2,3-dichloropyrrol-1-yl)phenol
approved: f
ligand name: neopyrrolomycin
type: NaturalProductLigand

spenolimycin
in ch i key: JXUOVTMVWNHOAJ-XLBYJKOOSA-N
in ch i: InChI=1S/C15H26N2O7/c1-6-5-7(21-4)15(20)14(22-6)23-13-11(19)8(16-2)10(18)9(17-3)12(13)24-15/h5-6,8-14,16-20H,1-4H3/t6-,8-,9+,10+,11+,12-,13-,14+,15+/m1/s1
comment: Spenolimycin, is a spectinomycin-like, aminocyclitol antibacterial <Reference id=39537/>. It was isolated from Streptomyces gilvospiralis sp. nov.
synonym: acmimycin
approved: f
ligand name: spenolimycin
type: NaturalProductLigand

DuP-721
canonical SMILES: CC(=O)NCC1CN(C(=O)O1)c1ccc(cc1)C(=O)C
isomeric SMILES: CC(=O)NCC1CN(C(=O)O1)c1ccc(cc1)C(=O)C
in ch i key: POXUJOYUVLWPQN-UHFFFAOYSA-N
in ch i: InChI=1S/C14H16N2O4/c1-9(17)11-3-5-12(6-4-11)16-8-13(20-14(16)19)7-15-10(2)18/h3-6,13H,7-8H2,1-2H3,(H,15,18)
comment: DuP-721 is an oxazolidinone antibacterial with Gram-positive and Gram-negative activity <Reference id=39536/><Reference id=39534/>. It was developed for activity against Staphylococcus aureus, and has equal activity against methicillin-sensitive and methicillin-resistant strains <Reference id=39535/>.
iupac name: N-[[3-(4-acetylphenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide
synonym: DuP 721
approved: f
ligand name: DuP-721
type: SyntheticOrganicLigand

CCG258747
in ch i key: KGSBEYKVWODBRD-ICSRJNTNSA-N
in ch i: InChI=1S/C28H27FN4O4/c29-23-7-5-17(11-22(23)28(34)31-14-25-21-3-1-2-4-24(21)32-33-25)20-9-10-30-13-18(20)15-35-19-6-8-26-27(12-19)37-16-36-26/h1-8,11-12,18,20,30H,9-10,13-16H2,(H,31,34)(H,32,33)/t18-,20-/m0/s1
comment: GRK2 subfamily-selective inhibitor.
iupac name: 5-[(3S,4R)-3-(1,3-benzodioxol-5-yloxymethyl)piperidin-4-yl]-2-fluoro-N-(2H-indazol-3-ylmethyl)benzamide
approved: f
ligand name: CCG258747
type: SyntheticOrganicLigand

acetylcysteine
canonical SMILES: SC[C@@H](C(=O)O)NC(=O)C
isomeric SMILES: SC[C@@H](C(=O)O)NC(=O)C
in ch i key: PWKSKIMOESPYIA-BYPYZUCNSA-N
in ch i: InChI=1S/C5H9NO3S/c1-3(7)6-4(2-10)5(8)9/h4,10H,2H2,1H3,(H,6,7)(H,8,9)/t4-/m0/s1
comment: Acetylcysteine is a prodrug for L-cysteine synthesis, and L-cysteine is a precursor to the biologic antioxidant glutathione. Hence adminstration of acetylcysteine replenishes glutathione stores.
iupac name: (2R)-2-acetamido-3-sulfanylpropanoic acid
xref: CHEMBL600
synonym: N-Acetyl-L-cysteine
synonym: N-Acetyl-cysteine
synonym: NAC
synonym: N-A-C Sustain®
synonym: Parvolex®
synonym: Ilube® (eye drops)
approved: t
ligand name: acetylcysteine
type: SyntheticOrganicLigand

tobramycin
in ch i key: NLVFBUXFDBBNBW-PBSUHMDJSA-N
in ch i: InChI=1S/C18H37N5O9/c19-3-9-8(25)2-7(22)17(29-9)31-15-5(20)1-6(21)16(14(15)28)32-18-13(27)11(23)12(26)10(4-24)30-18/h5-18,24-28H,1-4,19-23H2/t5-,6+,7+,8-,9+,10+,11-,12+,13+,14-,15+,16-,17+,18+/m0/s1
comment: Tobramycin is an aminoglycoside antibacterial that was originally isolated from Streptomyces tenebrarius. It is particularly effective against Gram-negative infections (especially Pseudomonas spp. infections). Like other aminoglycosides it is ototoxic and nephrotoxic.
iupac name: (2S,3R,4S,5S,6R)-4-amino-2-[(1S,2S,3R,4S,6R)-4,6-diamino-3-[(2R,3R,5S,6R)-3-amino-6-(aminomethyl)-5-hydroxyoxan-2-yl]oxy-2-hydroxycyclohexyl]oxy-6-(hydroxymethyl)oxane-3,5-diol
xref: CHEMBL1747
synonym: Tobi Podhaler®
synonym: Vantobra®
synonym: Bethkis®
synonym: Kitabis®
synonym: Tobradex® (tobramycin + dexamethasone)
approved: t
ligand name: tobramycin
type: NaturalProductLigand

eremomycin
in ch i key: UECIPBUIMXSXEI-BNSVOVDNSA-N
comment: Eremomycin (A82846A) is a glycopeptide, parenteral antibacterial with Gram-negative activity that was isolated from Actinomycete strain INA-238 <Reference id=39533/>. It was discovered to be highly toxic in vivo, but a derivative was subsequently developed as <Ligand id=10877/>.
xref: CHEMBL411769
synonym: A82846A
approved: f
ligand name: eremomycin
type: NaturalProductLigand

hedamycin
in ch i key: RZOFHOWMWMTHDX-UHFFFAOYSA-N
in ch i: InChI=1S/C41H50N2O11/c1-16-11-22-30(37-28(16)24(44)14-27(53-37)41(6)39(54-41)36-18(3)52-36)35(48)31-29(34(22)47)20(25-13-23(42(7)8)32(45)17(2)50-25)12-21(33(31)46)26-15-40(5,43(9)10)38(49)19(4)51-26/h11-12,14,17-19,23,25-26,32,36,38-39,45-46,49H,13,15H2,1-10H3
comment: Hedamycin is a microbial metabolite with antibacterial, antitrypanosomal <Reference id=39531/> and antitumour activities. It triggers cytotoxic DNA damage in human cells <Reference id=39531/>.
iupac name: 10-[4-(dimethylamino)-5-hydroxy-4,6-dimethyloxan-2-yl]-8-[4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]-11-hydroxy-5-methyl-2-[2-methyl-3-(3-methyloxiran-2-yl)oxiran-2-yl]naphtho[2,3-h]chromene-4,7,12-trione
xref: CHEMBL1979887
synonym: B26158
synonym: NSC-70929
synonym: antibiotic B 26,158
approved: f
ligand name: hedamycin
type: NaturalProductLigand

NSC-93169
canonical SMILES: CNC(=O)c1n[se]nc1N
isomeric SMILES: CNC(=O)c1n[se]nc1N
in ch i key: KVRRSRDUIXUGCU-UHFFFAOYSA-N
in ch i: InChI=1S/C4H6N4OSe/c1-6-4(9)2-3(5)8-10-7-2/h1H3,(H2,5,8)(H,6,9)
comment: NSC-93169 is a selenadiazole derivative antibacterial with Gram-positive activity <Reference id=39530/>.
iupac name: 4-amino-N-methyl-1,2,5-selenadiazole-3-carboxamide
synonym: NSC93169
synonym: NSC 93169
approved: f
ligand name: NSC-93169
type: SyntheticOrganicLigand

NSC-84963
canonical SMILES: NC(=O)c1n[se]nc1N
isomeric SMILES: NC(=O)c1n[se]nc1N
in ch i key: MTHSSXGAJGDHBL-UHFFFAOYSA-N
in ch i: InChI=1S/C3H4N4OSe/c4-2-1(3(5)8)6-9-7-2/h(H2,4,7)(H2,5,8)
comment: NSC-84963 is a selenadiazole derivative antibacterial with Gram-positive activity <Reference id=39530/>.
iupac name: 4-amino-1,2,5-selenadiazole-3-carboxamide
synonym: NSC 84963
synonym: NSC84963
approved: f
ligand name: NSC-84963
type: SyntheticOrganicLigand

DS-8587
in ch i key: JMXNWTLVUUGTDR-UTQQSMSJSA-N
in ch i: InChI=1S/C21H22F3N3O3/c1-10-16-11(18(28)12(19(29)30)7-27(16)15-6-13(15)22)5-14(23)17(10)26-8-20(24)3-2-4-21(20,25)9-26/h5,7,13,15H,2-4,6,8-9,25H2,1H3,(H,29,30)/t13-,15+,20-,21+/m0/s1
comment: DS-8587 is a broad-spectrum fluoroquinolone antibacterial <Reference id=39529/><Reference id=39528/>. It has antimicrobial activity against both Gram-positive and Gram-negative pathogens.
iupac name: 7-[(3aS,6aR)-6a-amino-3a-fluoro-3,4,5,6-tetrahydro-1H-cyclopenta[c]pyrrol-2-yl]-6-fluoro-1-[(1R,2S)-2-fluorocyclopropyl]-8-methyl-4-oxoquinoline-3-carboxylic acid
synonym: DS8587
approved: f
ligand name: DS-8587
type: SyntheticOrganicLigand

phleomycin
in ch i key: QRBLKGHRWFGINE-UGWAGOLRSA-N
comment: Phleomycins are a group of glycopeptide antibacterials found in Streptomyces species. They also possess anti-cancer activity through intercalation into DNA and disruption of the double helix.
iupac name: 2-[2-[2-[[2-[[4-[[2-[[6-amino-2-[3-amino-1-[(2,3-diamino-3-oxopropyl)amino]-3-oxopropyl]-5-methylpyrimidine-4-carbonyl]amino]-3-[(2R,3S,4S,5S,6S)-3-[(2S,3R,4R,5S)-4-carbamoyl-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)-3-methyloxan-2-yl]oxy-3-(1H-imidazol-5-yl)propanoyl]amino]-3-hydroxy-2-methylpentanoyl]amino]-3-oxobutanoyl]amino]ethyl]-4,5-dihydro-1,3-thiazol-4-yl]-1,3-thiazole-4-carboxamide
synonym: NSC 61586
synonym: NSC-61586
approved: f
ligand name: phleomycin
type: NaturalProductLigand

hesperetin
in ch i key: AIONOLUJZLIMTK-AWEZNQCLSA-N
in ch i: InChI=1S/C16H14O6/c1-21-13-3-2-8(4-10(13)18)14-7-12(20)16-11(19)5-9(17)6-15(16)22-14/h2-6,14,17-19H,7H2,1H3/t14-/m0/s1
comment: Hesperetin is a natural flavonoid. It has antibacterial activity against Gram-negative H. pylori <Reference id=39527/>.
iupac name: (2S)-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-2,3-dihydrochromen-4-one
xref: CHEMBL399121
synonym: NSC-57654
synonym: 3',5,7-Trihydroxy-4'-methoxyflavanone
synonym: NP-13
approved: f
ligand name: hesperetin
type: NaturalProductLigand

ethyl bromopyruvate
canonical SMILES: CCOC(=O)C(=O)CBr
isomeric SMILES: CCOC(=O)C(=O)CBr
in ch i key: VICYTAYPKBLQFB-UHFFFAOYSA-N
in ch i: InChI=1S/C5H7BrO3/c1-2-9-5(8)4(7)3-6/h2-3H2,1H3
comment: Ethyl bromopyruvate has broad-spectrum antibacterial activity against Gram-positive and Gram-negative bacteria <Reference id=39526/>.
iupac name: ethyl 3-bromo-2-oxopropanoate
xref: CHEMBL3185574
approved: f
ligand name: ethyl bromopyruvate
type: SyntheticOrganicLigand

nojirimycin
canonical SMILES: OC[C@H]1NC(O)[C@@H]([C@H]([C@@H]1O)O)O
isomeric SMILES: OC[C@H]1NC(O)[C@@H]([C@H]([C@@H]1O)O)O
in ch i key: BGMYHTUCJVZIRP-GASJEMHNSA-N
in ch i: InChI=1S/C6H13NO5/c8-1-2-3(9)4(10)5(11)6(12)7-2/h2-12H,1H2/t2-,3-,4+,5-,6?/m1/s1
comment: Nojirimycin is an aminoglycoside antibacterial with Gram-negative activity <Reference id=39525/>. It is produced by Streptomyces species, and chemically is an iminosugar.
iupac name: (3R,4S,5R,6R)-6-(hydroxymethyl)piperidine-2,3,4,5-tetrol
xref: CHEMBL120638
synonym: D-gluco-piperidinose
synonym: 5-amino-5-deoxy-D-glucopyranose
approved: f
ligand name: nojirimycin
type: NaturalProductLigand

Dup-105
in ch i key: RYTTWOVTZKVWTO-ZOZMEPSFSA-N
in ch i: InChI=1S/C13H16N2O4S/c1-9(16)14-7-11-8-15(13(17)19-11)10-3-5-12(6-4-10)20(2)18/h3-6,11H,7-8H2,1-2H3,(H,14,16)/t11-,20?/m0/s1
comment: DuP 105 is an oxazolidinone antibacterial <Reference id=39523/>. It has activity against Gram-positive bacteria.
iupac name: N-[[(5S)-3-(4-methylsulfinylphenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide
xref: CHEMBL316369
synonym: DuP 105
synonym: DuP105
approved: f
ligand name: Dup-105
type: SyntheticOrganicLigand

indanomycin
in ch i key: BAIPOTOKPGDCHA-MWBHXQFBSA-N
in ch i: InChI=1S/C31H43NO4/c1-5-21-13-16-25-24(21)15-14-23(28(25)29(33)26-11-8-18-32-26)10-7-9-22(6-2)30-19(3)12-17-27(36-30)20(4)31(34)35/h7-11,14-15,18-21,23-25,27-28,30,32H,5-6,12-13,16-17H2,1-4H3,(H,34,35)/b10-7+,22-9+/t19-,20+,21-,23+,24+,25+,27+,28+,30+/m0/s1
comment: Indanomycin (X-14547A) is an ionophore antibacterial <Reference id=39521/><Reference id=39522/>. It is synthesised by Streptomyces antibacterialus NRRL 8167 (a soil dwelling microbe) and is active against Gram-positive bacteria in vitro.
iupac name: (2R)-2-[(2R,5S,6R)-6-[(3E,5E)-6-[(1S,3aR,4S,5S,7aS)-1-ethyl-4-(1H-pyrrole-2-carbonyl)-2,3,3a,4,5,7a-hexahydro-1H-inden-5-yl]hexa-3,5-dien-3-yl]-5-methyloxan-2-yl]propanoic acid
synonym: X-14547A
approved: f
ligand name: indanomycin
type: NaturalProductLigand

ELX-02
in ch i key: KJBRSTPUILEBDR-DBMIJKFDSA-N
in ch i: InChI=1S/C19H38N4O10/c1-4(20)14-12(28)13(29)19(30-14)33-17-9(25)6(21)3-7(22)16(17)32-18-8(23)10(26)11(27)15(31-18)5(2)24/h4-19,24-29H,3,20-23H2,1-2H3/t4-,5+,6+,7-,8+,9-,10+,11-,12-,13+,14+,15+,16+,17+,18+,19-/m0/s1
comment: ELX-02 is a compound designed to restore CFTR function in people with CF who have nonsense mutations. Nonsense mutations (also known as “x” or “stop” mutations) in the CFTR gene cause the production of CFTR protein to stop prematurely. ELX-02 is intended allow lung cells to override these premature stop signals and make full-length, functional CFTR protein.
iupac name: (2R,3S,4R,5R,6S)-5-amino-6-[(1R,2R,3S,4R,6S)-4,6-diamino-2-[(2S,3R,4S,5R)-5-[(1S)-1-aminoethyl]-3,4-dihydroxyoxolan-2-yl]oxy-3-hydroxycyclohexyl]oxy-2-[(1R)-1-hydroxyethyl]oxane-3,4-diol
xref: CHEMBL2220482
synonym: ELX-02 (disulfate)
synonym: HY-114231B
synonym: CS-0095334
approved: f
ligand name: ELX-02
type: SyntheticOrganicLigand

N, N-bis (5-ethyl-2-hydroxybenzyl) methylamine
canonical SMILES: CCc1ccc(c(c1)CN(Cc1cc(CC)ccc1O)C)O
isomeric SMILES: CCc1ccc(c(c1)CN(Cc1cc(CC)ccc1O)C)O
in ch i key: COZATXGXDYUQGG-UHFFFAOYSA-N
in ch i: InChI=1S/C19H25NO2/c1-4-14-6-8-18(21)16(10-14)12-20(3)13-17-11-15(5-2)7-9-19(17)22/h6-11,21-22H,4-5,12-13H2,1-3H3
comment: A potent compound targeting oncogenic c-Myc ubiquitin-proteasomal degradation in lung cancer cells.
iupac name: 4-ethyl-2-[[(5-ethyl-2-hydroxyphenyl)methyl-methylamino]methyl]phenol
approved: f
ligand name: N, N-bis (5-ethyl-2-hydroxybenzyl) methylamine
type: SyntheticOrganicLigand

5-Hydroxymethyl-2-furfural
canonical SMILES: OCc1ccc(o1)C=O
isomeric SMILES: OCc1ccc(o1)C=O
in ch i key: NOEGNKMFWQHSLB-UHFFFAOYSA-N
in ch i: InChI=1S/C6H6O3/c7-3-5-1-2-6(4-8)9-5/h1-3,8H,4H2
comment: A component of natural medicinal honeys, blocks the ion conductance but not the water flux through human Aquaporin-1 (AQP1) channels, and impairs AQP1-dependent cell migration and invasiveness in cancer cell lines.
iupac name: 5-(hydroxymethyl)furan-2-carbaldehyde
xref: ChEMBL185885
approved: f
ligand name: 5-Hydroxymethyl-2-furfural
type: NaturalProductLigand

SAR247799
in ch i key: WRBZNIUFAKIIQG-UHFFFAOYSA-N
in ch i: InChI=1S/C21H16ClN3O5/c1-11-6-13(7-12(2)18(11)28-10-17(26)27)19-24-16-9-23-21(25-20(16)30-19)29-15-5-3-4-14(22)8-15/h3-9H,10H2,1-2H3,(H,26,27)
comment: Biased agonist of the S1P1 receptor which preferentially activates downstream G protein signaling to a greater extent than β-arrestin and internalization signaling pathways.
iupac name: 2-[4-[5-(3-chlorophenoxy)-[1,3]oxazolo[5,4-d]pyrimidin-2-yl]-2,6-dimethylphenoxy]acetic acid
approved: f
ligand name: SAR247799
type: SyntheticOrganicLigand

cefoxitin
in ch i key: WZOZEZRFJCJXNZ-ZBFHGGJFSA-N
in ch i: InChI=1S/C16H17N3O7S2/c1-25-16(18-10(20)5-9-3-2-4-27-9)13(23)19-11(12(21)22)8(6-26-15(17)24)7-28-14(16)19/h2-4,14H,5-7H2,1H3,(H2,17,24)(H,18,20)(H,21,22)/t14-,16+/m1/s1
comment: Cefoxitin is a parenteral, second-generation cephamycin, β-lactam antibacterial. The 7-alpha-methoxy functional group within the structure makes cefoxitin highly resistant to hydrolysis by some β-lactamases. Methicillin-resistant Staphylococcus aureus has acquired resistance to cefoxitin, via expression of the gene for penicillin binding protein 2a (PBP2a). Cefoxitin is active against a broad range of Gram-negative and Gram-positive bacteria, including anaerobes. It is inactive against most strains of Pseudomonas aeruginosa and many strains of Enterobacter cloacae.
iupac name: (6R,7S)-3-(carbamoyloxymethyl)-7-methoxy-8-oxo-7-[(2-thiophen-2-ylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
xref: CHEMBL996
synonym: Mefoxin®
synonym: MK-306
synonym: MK306
synonym: MK 306
synonym: CFX
synonym: Cenomycin®
approved: t
ligand name: cefoxitin
type: SyntheticOrganicLigand

cefotetan
in ch i key: SRZNHPXWXCNNDU-RHBCBLIFSA-N
in ch i: InChI=1S/C17H17N7O8S4/c1-23-16(20-21-22-23)34-4-5-3-33-15-17(32-2,14(31)24(15)7(5)11(29)30)19-9(26)13-35-12(36-13)6(8(18)25)10(27)28/h13,15H,3-4H2,1-2H3,(H2,18,25)(H,19,26)(H,27,28)(H,29,30)/t13?,15-,17+/m1/s1
comment: Cefotetan is a semi-synthetic, broad-spectrum, β-lactamase-resistant, second-generation cephalosporin antibacterial. Because of its inhibitory activity towards human aldehyde dehydrogenase, cefotetan produces an effect to ethanol similar to that produced by <Ligand id=7168/> (Antabuse).
iupac name: (6R,7S)-7-[[4-(2-amino-1-carboxy-2-oxoethylidene)-1,3-dithietane-2-carbonyl]amino]-7-methoxy-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
xref: CHEMBL474579
synonym: ICI 156834
synonym: ICI-156834
synonym: ICI156834
synonym: Cefotan®
synonym: Apatef®
approved: t
ligand name: cefotetan
type: SyntheticOrganicLigand

nitrofurantoin
canonical SMILES: O=C1NC(=O)N(C1)/N=C/c1ccc(o1)[N+](=O)[O-]
isomeric SMILES: O=C1NC(=O)N(C1)/N=C/c1ccc(o1)[N+](=O)[O-]
in ch i key: NXFQHRVNIOXGAQ-YCRREMRBSA-N
in ch i: InChI=1S/C8H6N4O5/c13-6-4-11(8(14)10-6)9-3-5-1-2-7(17-5)12(15)16/h1-3H,4H2,(H,10,13,14)/b9-3+
comment: The metabolically reduced form of nitrofurantoin is highly reactive, and disrupts many processes that are crucial for bacterial cell growth/survival. Organisms are said to be susceptible to nitrofurantoin if their minimum inhibitory concentration (MIC) is ≤32 μg/ml or less.
iupac name: 1-[(E)-(5-nitrofuran-2-yl)methylideneamino]imidazolidine-2,4-dione
xref: CHEMBL572
synonym: NSC-2107
synonym: NSC-44150
synonym: Macrobid®
synonym: Macrodantin®
synonym: Nitro Macro®
synonym: Furadantin®
approved: t
ligand name: nitrofurantoin
type: SyntheticOrganicLigand

cefazolin
in ch i key: MLYYVTUWGNIJIB-BXKDBHETSA-N
in ch i: InChI=1S/C14H14N8O4S3/c1-6-17-18-14(29-6)28-4-7-3-27-12-9(11(24)22(12)10(7)13(25)26)16-8(23)2-21-5-15-19-20-21/h5,9,12H,2-4H2,1H3,(H,16,23)(H,25,26)/t9-,12-/m1/s1
comment: Cefazolin is a β-lactam and first-generation cephalosporin antibacterial.
iupac name: (6R,7R)-3-[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanylmethyl]-8-oxo-7-[[2-(tetrazol-1-yl)acetyl]amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
xref: CHEMBL1435
synonym: CEZ
synonym: cephazolin
synonym: Ancef®
synonym: Kefzol®
synonym: SK&F-41558
approved: f
ligand name: cefazolin
type: SyntheticOrganicLigand

dapsone
canonical SMILES: Nc1ccc(cc1)S(=O)(=O)c1ccc(cc1)N
isomeric SMILES: Nc1ccc(cc1)S(=O)(=O)c1ccc(cc1)N
in ch i key: MQJKPEGWNLWLTK-UHFFFAOYSA-N
in ch i: InChI=1S/C12H12N2O2S/c13-9-1-5-11(6-2-9)17(15,16)12-7-3-10(14)4-8-12/h1-8H,13-14H2
comment: Dapsone is a sulfonamide-related antibacterial, antimalarial and anti-inflammatory drug. In bacteria it inhibits dihydropteroate synthase-mediated production of folic acid, which has the effect of disrupting the availability of thymidylate for DNA synthesis. The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
iupac name: 4-(4-aminophenyl)sulfonylaniline
xref: CHEMBL1043
synonym: NSC-6091
synonym: Aczone®
approved: t
ligand name: dapsone
type: SyntheticOrganicLigand

sulfamethoxazole
canonical SMILES: Nc1ccc(cc1)S(=O)(=O)Nc1noc(c1)C
isomeric SMILES: Nc1ccc(cc1)S(=O)(=O)Nc1noc(c1)C
in ch i key: JLKIGFTWXXRPMT-UHFFFAOYSA-N
in ch i: InChI=1S/C10H11N3O3S/c1-7-6-10(12-16-7)13-17(14,15)9-4-2-8(11)3-5-9/h2-6H,11H2,1H3,(H,12,13)
comment: Sulfamethoxazole is a sulfonamide antibacterial that has bacteriostatic activity. It inhibits the bacterial dihydropteroate synthase pathway which generates the folic acid that is essential for bacterial growth. It is active against Gram-negative and Gram-positive bacteria including Listeria monocytogenes and E. coli.
iupac name: 4-amino-N-(5-methyl-1,2-oxazol-3-yl)benzenesulfonamide
xref: CHEMBL443
synonym: SMX
synonym: RO 4-2130
synonym: RO-42130
synonym: STX-608
synonym: Gantanol®
approved: t
ligand name: sulfamethoxazole
type: SyntheticOrganicLigand

vancomycin
in ch i key: MYPYJXKWCTUITO-LYRMYLQWSA-N
comment: Vancomycin is a complex glycopeptide antibacterial that was originally isolated from Streptomyces orientalis. It has bactericidal activity against most organisms and is bacteriostatic vs. enterococci. Semisynthetic derivatives such as <Ligand id=10925/>, <Ligand id=10876/> and <Ligand id=10877/> are now available for clinical use.
xref: CHEMBL262777
synonym: Vancocin®
synonym: Vancor®
approved: t
ligand name: vancomycin
type: NaturalProductLigand

oxacillin
in ch i key: UWYHMGVUTGAWSP-JKIFEVAISA-N
in ch i: InChI=1S/C19H19N3O5S/c1-9-11(12(21-27-9)10-7-5-4-6-8-10)15(23)20-13-16(24)22-14(18(25)26)19(2,3)28-17(13)22/h4-8,13-14,17H,1-3H3,(H,20,23)(H,25,26)/t13-,14+,17-/m1/s1
comment: Oxacillin is a semi-synthetic penicillinase-resistant and acid-stable, a parenteral β-lactam (penicillin) antibacterial. It has replaced methicillin in clinical use.
iupac name: (2S,5R,6R)-3,3-dimethyl-6-[(5-methyl-3-phenyl-1,2-oxazole-4-carbonyl)amino]-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
xref: CHEMBL819
synonym: Bactocill®
approved: t
ligand name: oxacillin
type: SyntheticOrganicLigand

teicoplanin
in ch i key: BJNLLBUOHPVGFT-CAYRISATSA-N
comment: Teicoplanin is a glycopeptide antibacterial drug <Reference id=39488/>. Its spectrum of activity similar to that of vancomycin, with activity against Gram-positive bacteria including Staphylococci and Clostridium spp.
synonym: Targocid®
synonym: Antibiotic 8327A
synonym: teichomycin
synonym: MDL-507
synonym: MDL 507
synonym: teicoplanin A2
approved: t
ligand name: teicoplanin
type: SyntheticOrganicLigand

streptomycin
in ch i key: UCSJYZPVAKXKNQ-HZYVHMACSA-N
in ch i: InChI=1S/C21H39N7O12/c1-5-21(36,4-30)16(40-17-9(26-2)13(34)10(31)6(3-29)38-17)18(37-5)39-15-8(28-20(24)25)11(32)7(27-19(22)23)12(33)14(15)35/h4-18,26,29,31-36H,3H2,1-2H3,(H4,22,23,27)(H4,24,25,28)/t5-,6-,7+,8-,9-,10-,11+,12-,13-,14+,15+,16-,17-,18-,21+/m0/s1
comment: Streptomycin is an aminoglycoside antibacterial drug. Notably streptomycin was the first antibacterial cure for tuberculosis. As with other aminoglycosides, the most concerning side effects are renal and ear toxicities <Reference id=39483/>.
iupac name: 2-[(1R,2R,3S,4R,5R,6S)-3-(diaminomethylideneamino)-4-[(2R,3R,4R,5S)-3-[(2S,3S,4S,5R,6S)-4,5-dihydroxy-6-(hydroxymethyl)-3-(methylamino)oxan-2-yl]oxy-4-formyl-4-hydroxy-5-methyloxolan-2-yl]oxy-2,5,6-trihydroxycyclohexyl]guanidine
xref: CHEMBL372795
synonym: NSC-14083
synonym: Strepcen®
synonym: Gerox®
approved: t
ligand name: streptomycin
type: SyntheticOrganicLigand

ticarcillin
in ch i key: OHKOGUYZJXTSFX-KZFFXBSXSA-N
in ch i: InChI=1S/C15H16N2O6S2/c1-15(2)9(14(22)23)17-11(19)8(12(17)25-15)16-10(18)7(13(20)21)6-3-4-24-5-6/h3-5,7-9,12H,1-2H3,(H,16,18)(H,20,21)(H,22,23)/t7-,8-,9+,12-/m1/s1
comment: Ticarcillin is a broad-spectrum, semi-synthetic, parenteral penicillin (β-lactam) antibacterial for the treatment of Gram-negative bacteria. Bacteria that express β-lactamases are resistant to ticarcillin.
iupac name: (2S,5R,6R)-6-[[(2R)-2-carboxy-2-thiophen-3-ylacetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
xref: CHEMBL1449
synonym: BRL-2288
synonym: BRL2288
synonym: Timentin® (ticarcillin + clavulanate)
synonym: Ticar
approved: t
ligand name: ticarcillin
type: SyntheticOrganicLigand

pivmecillinam
in ch i key: NPGNOVNWUSPMDP-HLLBOEOZSA-N
in ch i: InChI=1S/C21H33N3O5S/c1-20(2,3)19(27)29-13-28-18(26)15-21(4,5)30-17-14(16(25)24(15)17)22-12-23-10-8-6-7-9-11-23/h12,14-15,17H,6-11,13H2,1-5H3/t14-,15+,17-/m1/s1
comment: Pivmecillinam is a penicillanic acid ester prodrug of mecillinam, and is a semisynthetic, broad spectrum β-lactam penicillin antibacterial. It is considered to be active only against Gram-negative bacteria.
xref: CHEMBL1650818
synonym: amdinocillin pivoxil
synonym: pivmecillinam hydrochloride
synonym: RO-10-9071
synonym: RO-109071
synonym: RO-109,071
synonym: Selexid®
approved: t
ligand name: pivmecillinam
type: SyntheticOrganicLigand

ofloxacin
in ch i key: GSDSWSVVBLHKDQ-UHFFFAOYSA-N
in ch i: InChI=1S/C18H20FN3O4/c1-10-9-26-17-14-11(16(23)12(18(24)25)8-22(10)14)7-13(19)15(17)21-5-3-20(2)4-6-21/h7-8,10H,3-6,9H2,1-2H3,(H,24,25)
comment: Ofloxacin is a second generation fluoroquinolone antibacterial.
xref: CHEMBL4
synonym: Floxin®
synonym: Tarivid®
synonym: Exocin® (eye drops)
synonym: DL-8280
synonym: HOE-280
synonym: OFX
approved: t
ligand name: ofloxacin
type: SyntheticOrganicLigand

oxytetracycline
in ch i key: OWFJMIVZYSDULZ-PXOLEDIWSA-N
in ch i: InChI=1S/C22H24N2O9/c1-21(32)7-5-4-6-8(25)9(7)15(26)10-12(21)17(28)13-14(24(2)3)16(27)11(20(23)31)19(30)22(13,33)18(10)29/h4-6,12-14,17,25-26,28,30,32-33H,1-3H3,(H2,23,31)/t12-,13-,14+,17+,21-,22+/m1/s1
comment: Oxytetracycline is a tetracycline class antibacterial. It has activity against Gram-positive and -negative bacteria, including Mycoplasma pneumoniae, Pasteurella pestis, Escherichia coli, Haemophilus influenzae, and Diplococcus pneumoniae.
iupac name: (4S,4aR,5S,5aR,6S,12aR)-4-(dimethylamino)-1,5,6,10,11,12a-hexahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide
xref: CHEMBL1517
synonym: Terramycin®
synonym: E703
synonym: NSC-9169
approved: t
ligand name: oxytetracycline
type: SyntheticOrganicLigand

moxifloxacin
in ch i key: FABPRXSRWADJSP-MEDUHNTESA-N
in ch i: InChI=1S/C21H24FN3O4/c1-29-20-17-13(19(26)14(21(27)28)9-25(17)12-4-5-12)7-15(22)18(20)24-8-11-3-2-6-23-16(11)10-24/h7,9,11-12,16,23H,2-6,8,10H2,1H3,(H,27,28)/t11-,16+/m0/s1
comment: Moxifloxacin is a fourth generation fluoroquinolone antibacterial. Compared to earlier generation fluoroquinolones it has expanded activity against Gram-positive bacteria and some atypical pathogens.
iupac name: 7-[(4aS,7aS)-1,2,3,4,4a,5,7,7a-octahydropyrrolo[3,4-b]pyridin-6-yl]-1-cyclopropyl-6-fluoro-8-methoxy-4-oxoquinoline-3-carboxylic acid
xref: CHEMBL32
synonym: BAY-12-8039
synonym: BAY-128039
synonym: Avelox®
synonym: MOXIVIG® (opthalmic solution)
synonym: BAY128039
synonym: MFX
approved: t
ligand name: moxifloxacin
type: SyntheticOrganicLigand

phenoxymethylpenicillin
in ch i key: BPLBGHOLXOTWMN-MBNYWOFBSA-N
in ch i: InChI=1S/C16H18N2O5S/c1-16(2)12(15(21)22)18-13(20)11(14(18)24-16)17-10(19)8-23-9-6-4-3-5-7-9/h3-7,11-12,14H,8H2,1-2H3,(H,17,19)(H,21,22)/t11-,12+,14-/m1/s1
comment: Phenoxymethylpenicillin is a β-lactam, natural penicillin antibacterial. It has broad-spectrum activity against Gram-positive aerobes, limited activity against Gram-negative organisms, and is not generally used against anaerobes.
xref: CHEMBL615
synonym: Oracillin®
synonym: penicillin V
synonym: PC Pen VK®
synonym: Pen-V®
synonym: Penicillin VK
synonym: PNV
approved: t
ligand name: phenoxymethylpenicillin
type: NaturalProductLigand

flucloxacillin
in ch i key: UIOFUWFRIANQPC-JKIFEVAISA-N
comment: Flucloxacillin is a narrow-spectrum, semisynthetic penicillin (β-lactam) antibacterial. It is β-lactamase stable.
iupac name: (2S,5R,6R)-6-[[3-(2-chloro-6-fluorophenyl)-5-methyl-1,2-oxazole-4-carbonyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
xref: CHEMBL222645
synonym: floxacillin
synonym: BRL 2039
synonym: BRL-2039
synonym: BRL2039
approved: t
ligand name: flucloxacillin
type: SyntheticOrganicLigand

piperacillin
in ch i key: IVBHGBMCVLDMKU-GXNBUGAJSA-N
in ch i: InChI=1S/C23H27N5O7S/c1-4-26-10-11-27(19(32)18(26)31)22(35)25-13(12-8-6-5-7-9-12)16(29)24-14-17(30)28-15(21(33)34)23(2,3)36-20(14)28/h5-9,13-15,20H,4,10-11H2,1-3H3,(H,24,29)(H,25,35)(H,33,34)/t13-,14-,15+,20-/m1/s1
comment: Piperacillin is a broad-spectrum semisynthetic, ampicillin-derived antibacterial.
iupac name: (2S,5R,6R)-6-[[(2R)-2-[(4-ethyl-2,3-dioxopiperazine-1-carbonyl)amino]-2-phenylacetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
xref: CHEMBL702
synonym: PIPC
synonym: CL 227,193
synonym: CL-227193
synonym: T-1220
synonym: Tazocin® (piperacillin + tazobactam)
approved: t
ligand name: piperacillin
type: SyntheticOrganicLigand

BAY1125976
in ch i key: JBGYKRAZYDNCNV-UHFFFAOYSA-N
in ch i: InChI=1S/C23H21N5O/c24-22(29)18-11-12-19-26-20(21(28(19)27-18)16-5-2-1-3-6-16)15-7-9-17(10-8-15)23(25)13-4-14-23/h1-3,5-12H,4,13-14,25H2,(H2,24,29)
comment: BAY1125976 is an allosteric inhibitor of AKT1 and AKT2 that is being developed by Bayer for oncology potential. It is claimed as example 5 in Bayer's patent WO2012136776A1 <Reference id=39464/>.
iupac name: 2-[4-(1-aminocyclobutyl)phenyl]-3-phenylimidazo[1,2-b]pyridazine-6-carboxamide
synonym: BAY-1125976
synonym: BAY 1125976
synonym: Example 5 [WO2012136776A1]
approved: f
ligand name: BAY1125976
type: SyntheticOrganicLigand

Thio-THIP
canonical SMILES: O=c1[nH]sc2c1CCNC2
isomeric SMILES: O=c1[nH]sc2c1CCNC2
in ch i key: DZYJTJJQGHXSFN-UHFFFAOYSA-N
in ch i: InChI=1S/C6H8N2OS/c9-6-4-1-2-7-3-5(4)10-8-6/h7H,1-3H2,(H,8,9)
comment: α4β1/3δ GABAA receptor orthosteric agonist.
iupac name: 4,5,6,7-tetrahydro-[1,2]thiazolo[5,4-c]pyridin-3-one
xref: CHEMBL170539
approved: f
ligand name: Thio-THIP
type: SyntheticOrganicLigand

ertapenem
in ch i key: JUZNIMUFDBIJCM-ANEDZVCMSA-N
comment: Ertapenem is a carbapenem and broad-spectrum β-lactam antibacterial.
iupac name: (4R,5S,6S)-3-[(3S,5S)-5-[(3-carboxyphenyl)carbamoyl]pyrrolidin-3-yl]sulfanyl-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
xref: CHEMBL1359
synonym: L-749345
synonym: MK-0826
synonym: MK-826
synonym: Invanz®
approved: t
ligand name: ertapenem
type: SyntheticOrganicLigand

barusiban
in ch i key: UGNGRKKDUVKQDF-IHOMMZCZSA-N
in ch i: InChI=1S/C40H63N9O8S/c1-6-23(3)34-38(55)46-31(20-32(42)51)36(53)45-29(40(57)49(5)26(22-50)11-10-16-41)14-17-58-18-15-33(52)44-30(19-25-21-43-28-13-9-8-12-27(25)28)37(54)47-35(24(4)7-2)39(56)48-34/h8-9,12-13,21,23-24,26,29-31,34-35,43,50H,6-7,10-11,14-20,22,41H2,1-5H3,(H2,42,51)(H,44,52)(H,45,53)(H,46,55)(H,47,54)(H,48,56)/t23-,24+,26+,29+,30-,31+,34+,35+/m1/s1
comment: Barusiban (FE 200440) is an oxytocin receptor antagonist <Reference id=39428/><Reference id=39423/><Reference id=39424/>. It was developed by Ferring Pharmaceuticals as a tocolytic agent, to counteract oxytocin-induced myometrial contractions <Reference id=7336/>. Chemically it is a synthetic cyclic hexapeptide containing five unnatural amino acids and only one D-amino acid.
iupac name: (4S,7S,10S,13S,16R)-N-[(2S)-5-amino-1-hydroxypentan-2-yl]-7-(2-amino-2-oxoethyl)-13-[(2S)-butan-2-yl]-10-[(2R)-butan-2-yl]-16-(1H-indol-3-ylmethyl)-N-methyl-6,9,12,15,18-pentaoxo-1-thia-5,8,11,14,17-pentazacycloicosane-4-carboxamide
xref: CHEMBL2218898
synonym: C4.6,S1-cyclo[N-(3-sulfanylpropanoyl)-D-tryptophyl-L-isoleucyl-L-alloisoleucyl-L-asparaginyl-L-2-aminobutanoyl-N-methyl-L-ornithinol]
synonym: FE-200440
synonym: FE 200 440
approved: f
ligand name: barusiban
type: PeptideLigand

ML351
canonical SMILES: CNc1oc(nc1C#N)c1cccc2c1cccc2
isomeric SMILES: CNc1oc(nc1C#N)c1cccc2c1cccc2
in ch i key: DYXYXTDIFMDJIR-UHFFFAOYSA-N
in ch i: InChI=1S/C15H11N3O/c1-17-15-13(9-16)18-14(19-15)12-8-4-6-10-5-2-3-7-11(10)12/h2-8,17H,1H3
comment: ML351 is a potent and selective inhibitor of human 15-lipoxygenase-1 <Reference id=37204/>. It was used as a probe to demonstrate proof-of-concept of the therapeutic potential of selective inhibition of 15-LOX-1 in stroke models.
iupac name: 5-(methylamino)-2-naphthalen-1-yl-1,3-oxazole-4-carbonitrile
approved: f
ligand name: ML351
type: SyntheticOrganicLigand

demeclocycline
in ch i key: GUXHBMASAHGULD-SEYHBJAFSA-N
in ch i: InChI=1S/C21H21ClN2O8/c1-24(2)14-7-5-6-10(16(27)12-9(25)4-3-8(22)11(12)15(6)26)18(29)21(7,32)19(30)13(17(14)28)20(23)31/h3-4,6-7,14-15,25-27,30,32H,5H2,1-2H3,(H2,23,31)/t6-,7-,14-,15-,21-/m0/s1
comment: Demeclocycline is a tetracycline antibacterial which was derived from a mutant strain of Streptomyces aureofaciens.
iupac name: (4S,4aS,5aS,6S,12aR)-7-chloro-4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-3,12-dioxo-4a,5,5a,6-tetrahydro-4H-tetracene-2-carboxamide
xref: CHEMBL1591
synonym: Declomycin®
synonym: Ledermycin®
approved: f
ligand name: demeclocycline
type: SyntheticOrganicLigand

lymecycline
in ch i key: PZTCVADFMACKLU-UEPZRUIBSA-N
in ch i: InChI=1S/C29H38N4O10/c1-28(42)13-7-6-9-17(34)18(13)22(35)19-14(28)11-15-21(33(2)3)23(36)20(25(38)29(15,43)24(19)37)26(39)32-12-31-10-5-4-8-16(30)27(40)41/h6-7,9,14-16,21,31,34-35,38,42-43H,4-5,8,10-12,30H2,1-3H3,(H,32,39)(H,40,41)/t14-,15-,16-,21-,28+,29-/m0/s1
comment: Lymecycline is a tetracycline-based broad-spectrum antibacterial <Reference id=39473/>. It is substantially more soluble than tetracycline, so can be used at lower doses. Lymecycline also has anti-protozoal activity.
iupac name: (2S)-6-[[[(4S,4aS,5aS,6S,12aR)-4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carbonyl]amino]methylamino]-2-aminohexanoic acid
xref: CHEMBL2103929
synonym: N-Lysinomethyltetracycline
synonym: Tetralysal®
synonym: tetracycline-L Methylene-Lysine
approved: t
ligand name: lymecycline
type: SyntheticOrganicLigand

levofloxacin
in ch i key: GSDSWSVVBLHKDQ-JTQLQIEISA-N
in ch i: InChI=1S/C18H20FN3O4/c1-10-9-26-17-14-11(16(23)12(18(24)25)8-22(10)14)7-13(19)15(17)21-5-3-20(2)4-6-21/h7-8,10H,3-6,9H2,1-2H3,(H,24,25)/t10-/m0/s1
comment: Levofloxacin is a broad-spectrum, third-generation fluoroquinolone antibacterial.
xref: CHEMBL33
synonym: Quinsair®
synonym: Levaquin®
synonym: DR-3355
approved: t
ligand name: levofloxacin
type: SyntheticOrganicLigand

clarithromycin
in ch i key: AGOYDEPGAOXOCK-KCBOHYOISA-N
in ch i: InChI=1S/C38H69NO13/c1-15-26-38(10,45)31(42)21(4)28(40)19(2)17-37(9,47-14)33(52-35-29(41)25(39(11)12)16-20(3)48-35)22(5)30(23(6)34(44)50-26)51-27-18-36(8,46-13)32(43)24(7)49-27/h19-27,29-33,35,41-43,45H,15-18H2,1-14H3/t19-,20-,21+,22+,23-,24+,25+,26-,27+,29-,30+,31-,32+,33-,35+,36-,37-,38-/m1/s1
comment: Clarithromycin is a semisynthetic macrolide antibacterial. Structurally it is the 6-O-methyl ether of erythromycin A.
iupac name: (3R,4S,5S,6R,7R,9R,11R,12R,13S,14R)-6-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-14-ethyl-12,13-dihydroxy-4-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-7-methoxy-3,5,7,9,11,13-hexamethyl-oxacyclotetradecane-2,10-dione
xref: CHEMBL1741
synonym: A-56268
synonym: ABBOTT-56268
synonym: TE-031
synonym: TE031
synonym: Biaxin®
synonym: 6-O-methylerythromycin
synonym: Klaricid®
approved: t
ligand name: clarithromycin
type: SyntheticOrganicLigand

cefuroxime
in ch i key: JFPVXVDWJQMJEE-IZRZKJBUSA-N
in ch i: InChI=1S/C16H16N4O8S/c1-26-19-9(8-3-2-4-27-8)12(21)18-10-13(22)20-11(15(23)24)7(5-28-16(17)25)6-29-14(10)20/h2-4,10,14H,5-6H2,1H3,(H2,17,25)(H,18,21)(H,23,24)/b19-9-/t10-,14-/m1/s1
comment: Cefuroxime is a semisynthetic, second-generation cephalosporin antibacterial. It has broad-spectrum activity and is β-lactamase-resistant. Oral formulations contain the prodrug cefuroxime axetil.
iupac name: (6R,7R)-3-(carbamoyloxymethyl)-7-[[(2Z)-2-(furan-2-yl)-2-methoxyiminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
xref: CHEMBL1436
synonym: Ceftin®
synonym: Kefurox®
synonym: Zinacef®
synonym: CXM
approved: t
ligand name: cefuroxime
type: SyntheticOrganicLigand

ceftaroline fosamil
in ch i key: ZCCUWMICIWSJIX-NQJJCJBVSA-N
comment: Ceftaroline fosamil is a fifth-generation cephalosporin prodrug which is hydrolysed to the active form, ceftaroline, in vivo. It has anti-MRSA activity <Reference id=39450/>. Ceftaroline was removed from the World Health Organization's List of Essential Medicines in 2019.
iupac name: (6R,7R)-7-[[(2Z)-2-ethoxyimino-2-[5-(phosphonoamino)-1,2,4-thiadiazol-3-yl]acetyl]amino]-3-[[4-(1-methylpyridin-1-ium-4-yl)-1,3-thiazol-2-yl]sulfanyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
xref: CHEMBL501122
synonym: PPI-0903
synonym: TAK-599
synonym: Teflaro®
synonym: Zinforo®
approved: t
ligand name: ceftaroline fosamil
type: SyntheticOrganicLigand

cefaclor
in ch i key: QYIYFLOTGYLRGG-UHFFFAOYSA-N
comment: This is the structure for the anhydrous molecule. Cefaclor is second generation cephalosporin. Distaclor capsules contain cefaclor monohydrate as the active ingredient.
iupac name: (6R,7R)-7-[[(2R)-2-amino-2-phenylacetyl]amino]-3-chloro-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
xref: CHEMBL680
synonym: Lilly 99638
synonym: Ceclor®
synonym: Raniclor®
approved: t
ligand name: cefaclor
type: SyntheticOrganicLigand

amikacin
in ch i key: LKCWBDHBTVXHDL-RMDFUYIESA-N
in ch i: InChI=1S/C22H43N5O13/c23-2-1-8(29)20(36)27-7-3-6(25)18(39-22-16(34)15(33)13(31)9(4-24)37-22)17(35)19(7)40-21-14(32)11(26)12(30)10(5-28)38-21/h6-19,21-22,28-35H,1-5,23-26H2,(H,27,36)/t6-,7+,8-,9+,10+,11-,12+,13+,14+,15-,16+,17-,18+,19-,21+,22+/m0/s1
comment: Amikacin is a semi-synthetic aminoglycoside antibacterial that is active against a broad spectrum of Gram-negative organisms, including pseudomonas and some Gram-positive organisms (principally Staphylococcus aureus, including some methicillin-resistant strains). It is a kanamycin derivative. Functionally it binds to the bacterial 30S ribosomal subunit and disrupts protein synthesis, thereby creating its bactericidal effect.
iupac name: (2S)-4-amino-N-[(1R,2S,3S,4R,5S)-5-amino-2-[(2S,3R,4S,5S,6R)-4-amino-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4-[(2R,3R,4S,5S,6R)-6-(aminomethyl)-3,4,5-trihydroxyoxan-2-yl]oxy-3-hydroxycyclohexyl]-2-hydroxybutanamide
xref: CHEMBL177
synonym: BB-K8
synonym: AMK
synonym: Amikin®
synonym: Arikayce liposomal®
approved: t
ligand name: amikacin
type: SyntheticOrganicLigand

fluticasone furoate
in ch i key: XTULMSXFIHGYFS-VLSRWLAYSA-N
in ch i: InChI=1S/C27H29F3O6S/c1-14-9-16-17-11-19(29)18-10-15(31)6-7-24(18,2)26(17,30)21(32)12-25(16,3)27(14,23(34)37-13-28)36-22(33)20-5-4-8-35-20/h4-8,10,14,16-17,19,21,32H,9,11-13H2,1-3H3/t14-,16+,17+,19+,21+,24+,25+,26+,27+/m1/s1
comment: A synthetic glucocorticoid (glucocorticoid receptor agonist) available as an inhaler and nasal spray for various inflammatory indications.
iupac name: [(6S,8S,9R,10S,11S,13S,14S,16R,17R)-6,9-difluoro-17-(fluoromethylsulfanylcarbonyl)-11-hydroxy-10,13,16-trimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl] furan-2-carboxylate
xref: CHEMBL1676
synonym: FF
synonym: Veramyst
synonym: Avamys
synonym: Arnuity Ellipta
synonym: Flonase Sensimist
approved: t
ligand name: fluticasone furoate
type: SyntheticOrganicLigand

selgantolimod
canonical SMILES: CCCC[C@@](Nc1nc(N)nc2c1ncc(c2)F)(CO)C
isomeric SMILES: CCCC[C@@](Nc1nc(N)nc2c1ncc(c2)F)(CO)C
in ch i key: HTCJUBZBSJQWBW-CQSZACIVSA-N
in ch i: InChI=1S/C14H20FN5O/c1-3-4-5-14(2,8-21)20-12-11-10(18-13(16)19-12)6-9(15)7-17-11/h6-7,21H,3-5,8H2,1-2H3,(H3,16,18,19,20)/t14-/m1/s1
comment: Selgantolimod (GS-9688) is an investigational, selective and orally active TLR8 agonist <Reference id=39421/>. It was designed to treat chronic hepatitis B infection.
iupac name: (R)-2-((2-amino-7-fluoropyrido[3,2-d]pyrimidin-4-yl)amino)-2-methylhexan-1-ol
synonym: GS-9688
synonym: GS9688
synonym: compound (R)-7 [PMID: 32407112]
approved: f
ligand name: selgantolimod
type: SyntheticOrganicLigand

OMO-1
in ch i key: KOAWAWHSMVKCON-UHFFFAOYSA-N
in ch i: InChI=1S/C20H12F2N6/c21-20(22,15-3-4-16-14(12-15)2-1-9-24-16)19-26-25-18-6-5-17(27-28(18)19)13-7-10-23-11-8-13/h1-12H
comment: OMO-1 (formerly JNJ-38877618) is a potent, highly selective and orally bioavailable MET kinase inhibitor. It is being investigated as an anti-tumour agent in advanced solid malignancies. The chemical structure of OMO-1 is one of those claimed in Janssen patent WO2007075567A1 <Reference id=38337/>.
iupac name: 6-[difluoro-(6-pyridin-4-yl-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methyl]quinoline
synonym: OMO1
synonym: JNJ-38877618
synonym: JNJ38877618
synonym: example 60 [WO2007075567A1]
approved: f
ligand name: OMO-1
type: SyntheticOrganicLigand

ciprofloxacin
in ch i key: MYSWGUAQZAJSOK-UHFFFAOYSA-N
in ch i: InChI=1S/C17H18FN3O3/c18-13-7-11-14(8-15(13)20-5-3-19-4-6-20)21(10-1-2-10)9-12(16(11)22)17(23)24/h7-10,19H,1-6H2,(H,23,24)
comment: Ciprofloxacin is a synthetic, broad spectrum second generation fluoroquinolone antibacterial.
iupac name: 1-cyclopropyl-6-fluoro-4-oxo-7-piperazin-1-ylquinoline-3-carboxylic acid
xref: CHEMBL8
synonym: Cetraxal®
synonym: Ciloxan®
synonym: CPFX
synonym: Cipro®
synonym: Proquin XR
synonym: BAY-O-9867
synonym: BAY-O9867
approved: t
ligand name: ciprofloxacin
type: SyntheticOrganicLigand

chloramphenicol
canonical SMILES: OC[C@H]([C@@H](c1ccc(cc1)[N+](=O)[O-])O)NC(=O)C(Cl)Cl
isomeric SMILES: OC[C@H]([C@@H](c1ccc(cc1)[N+](=O)[O-])O)NC(=O)C(Cl)Cl
in ch i key: WIIZWVCIJKGZOK-RKDXNWHRSA-N
comment: Chloramphenicol is a semisynthetic, broad-spectrum antibacterial derived from Streptomyces venequelae. Its activity is primarily bacteriostatic.
iupac name: 2,2-dichloro-N-[(1R,2R)-1,3-dihydroxy-1-(4-nitrophenyl)propan-2-yl]acetamide
xref: CHEMBL130
synonym: Brolene®
synonym: chloromycetin
approved: t
ligand name: chloramphenicol
type: SyntheticOrganicLigand

adagrasib
in ch i key: PEMUGDMSUDYLHU-ZEQRLZLVSA-N
comment: Adagrasib (MRTX849) is a clinical lead covalent inhibitor of KRASG12C that was designed for anti-cancer potential <Reference id=39420/>. It is highly selective as it binds directly to Cys12 of the KRASG12C mutant protein.
synonym: compound 20 [PMID: 32250617]
synonym: MRTX-849
synonym: MRTX849
approved: f
ligand name: adagrasib
type: SyntheticOrganicLigand

amoxicillin
in ch i key: LSQZJLSUYDQPKJ-NJBDSQKTSA-N
in ch i: InChI=1S/C16H19N3O5S/c1-16(2)11(15(23)24)19-13(22)10(14(19)25-16)18-12(21)9(17)7-3-5-8(20)6-4-7/h3-6,9-11,14,20H,17H2,1-2H3,(H,18,21)(H,23,24)/t9-,10-,11+,14-/m1/s1
comment: Amoxicillin is a widely used penicillin class antibacterial.
iupac name: (2S,5R,6R)-6-[[(2R)-2-amino-2-(4-hydroxyphenyl)acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
xref: CHEMBL1082
synonym: Amoxil®
synonym: Trimox®
synonym: Moxatag®
synonym: co-amoxiclav (amoxicillin + clavulanic acid)
synonym: BRL-2333
synonym: NSC-277174
approved: t
ligand name: amoxicillin
type: SyntheticOrganicLigand

ampicillin
in ch i key: AVKUERGKIZMTKX-NJBDSQKTSA-N
in ch i: InChI=1S/C16H19N3O4S/c1-16(2)11(15(22)23)19-13(21)10(14(19)24-16)18-12(20)9(17)8-6-4-3-5-7-8/h3-7,9-11,14H,17H2,1-2H3,(H,18,20)(H,22,23)/t9-,10-,11+,14-/m1/s1
comment: Ampicillin is a broad-spectrum, semi-synthetic, β-lactam penicillin class antibacterial. It is resistant to hydrolysis by a variety of β-lactamases, so can be to treat a diverse range of infections caused by Gram-positive and Gram-negative infections.
iupac name: (2S,5R,6R)-6-[[(2R)-2-amino-2-phenylacetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
xref: CHEMBL174
synonym: KS-R1
synonym: Penbritin®
synonym: aminobenzylpenicillin
synonym: Principen®
synonym: Polycillin
approved: t
ligand name: ampicillin
type: SyntheticOrganicLigand

SR101099
in ch i key: XCIGPFMHSRYJDG-UHFFFAOYSA-N
in ch i: InChI=1S/C31H36ClN3O4/c1-21-10-5-6-11-23(21)24-13-15-26(29(36)34-31(30(37)38)16-7-4-8-17-31)33-28(24)22-12-14-25(32)27(20-22)39-19-9-18-35(2)3/h5-6,10-15,20H,4,7-9,16-19H2,1-3H3,(H,34,36)(H,37,38)
comment: Potent, selective and orally long-acting UT receptor (urotensin II receptor) competitive antagonist inhibiting not only urotensin II receptor but also urotensin related peptide activities. SAR101099 is the hydrochloride, the parent compound structure can be viewed here.
iupac name: 1-[[6-[4-chloro-3-[3-(dimethylamino)propoxy]phenyl]-5-(2-methylphenyl)pyridine-2-carbonyl]amino]cyclohexane-1-carboxylic acid
synonym: SAR 101099
synonym: SAR-101099
approved: f
ligand name: SR101099
type: SyntheticOrganicLigand

glepaglutide
in ch i key: DOAUQKRTILFGHV-PDCMDPCFSA-N
comment: Glepaglutide (ZP1848, Zealand Pharma) is a long-acting human glucagon like peptide-2 (GLP-2) analogue with a C-terminal hexa-lysine addition. The wild type peptide sequence is HADGSFSDEMNTILDNLAARDFINWLIQTKITD, compared to the glepaglutide sequence which is HGEGTFSSELATILDALAARDFIAWLIATKITDKKKKKK (the hexa-lysine is inderlined). GLP-2 receptor agonists have therapeutic potential in clinical indications with compromised absorptive capacity at the intestinal mucosa, such as in short bowel syndrome. GLP2 analogues have been designed to be less susceptible to enzymatic cleavage and renal clearance and hence have an improved circulating half-life compared to the endogenous peptide. <Ligand id=7049/> is already approved but has a once-daily injection regimen, so longer-acting analogues are still of development interest.
synonym: ZP1848
synonym: ZP-1848
approved: f
ligand name: glepaglutide
type: PeptideLigand

livoletide
in ch i key: JXPWLIYXIWGWSA-CLBRJLNISA-N
in ch i: InChI=1S/C40H63N15O13/c1-19(2)31-38(67)51-23(8-11-29(42)58)34(63)53-26(17-56)39(68)55-14-4-6-27(55)37(66)50-24(9-12-30(59)60)33(62)52-25(15-20-16-45-18-47-20)36(65)49-22(7-10-28(41)57)32(61)48-21(35(64)54-31)5-3-13-46-40(43)44/h16,18-19,21-27,31,56H,3-15,17H2,1-2H3,(H2,41,57)(H2,42,58)(H,45,47)(H,48,61)(H,49,65)(H,50,66)(H,51,67)(H,52,62)(H,53,63)(H,54,64)(H,59,60)(H4,43,44,46)/t21-,22-,23-,24-,25-,26-,27-,31-/m0/s1
comment: Livoletide (AZP-531) is a first-in-class analogue of unacylated ghrelin (UAG) <Reference id=39410/>. The exact mechanism of action is still unclear. When UAG is co-administered with ghrelin it is reported to act either as a functional antagonist or is acting via another receptor <Reference id=39410/><Reference id=39413/>. Other studies suggest that UAG is a full agonist <Reference id=39411/>.
xref: CHEMBL2029605
synonym: AZP-531
synonym: AZP531
synonym: Des-acyl ghrelin
synonym: Cyclo(des-acyl ghrelin(6-13))
approved: f
ligand name: livoletide
type: PeptideLigand

GC-376
in ch i key: BSPZFJDYQHDZNR-ASPXRTSYSA-N
in ch i: InChI=1S/C21H31N3O8S/c1-13(2)10-16(24-21(28)32-12-14-6-4-3-5-7-14)19(26)23-17(20(27)33(29,30)31)11-15-8-9-22-18(15)25/h3-7,13,15-17,20,27H,8-12H2,1-2H3,(H,22,25)(H,23,26)(H,24,28)(H,29,30,31)/t15?,16-,17-,20?/m0/s1
comment: GC-376 is an inhibitor of viral proteases, in particular of the 3CL protease (3CL-pro; Mpro) of coronaviruses and norovirus <Reference id=39409/><Reference id=39408/>.
iupac name: (2S)-1-hydroxy-2-[[(2S)-4-methyl-2-(phenylmethoxycarbonylamino)pentanoyl]amino]-3-(2-oxopyrrolidin-3-yl)propane-1-sulfonic acid
xref: CHEMBL2365410
synonym: GC376
synonym: compound 7a [PMID: 23218713]
approved: f
ligand name: GC-376
type: SyntheticOrganicLigand

asunaprevir
in ch i key: XRWSZZJLZRKHHD-WVWIJVSJSA-N
comment: Asunaprevir (BMS-650032) is an orally bioavailable, oligopeptide-based inhibitor of the nonstructural protein 3 (NS3), from hepatitis C virus (HCV) <Reference id=39406/>. NS3, is a serine protease that is essential for proteolytic cleavages within the HCV polyprotein, a function that is key during HCV viral RNA replication. More recently asunaprevir has been reported to inhibit the papain-like protease (PL-pro, nsp3) in a number of coronaviruses <Reference id=39404/>.
iupac name: tert-butyl N-[(2S)-1-[(2S,4R)-4-(7-chloro-4-methoxyisoquinolin-1-yl)oxy-2-[[(1R,2S)-1-(cyclopropylsulfonylcarbamoyl)-2-ethenylcyclopropyl]carbamoyl]pyrrolidin-1-yl]-3,3-dimethyl-1-oxobutan-2-yl]carbamate
xref: CHEMBL2105735
synonym: BMS-650032
synonym: BMS650032
synonym: Sunvepra™
synonym: compound 24 [PMID: 24564672]
approved: t
ligand name: asunaprevir
type: SyntheticOrganicLigand

compound 16 [PMID: 31955138]
canonical SMILES: Sc1nnc(n1NC1CCC=C1)NNc1ccc(cc1)I
isomeric SMILES: Sc1nnc(n1NC1CCC=C1)NNc1ccc(cc1)I
in ch i key: HZJRZVOMEGOUMN-UHFFFAOYSA-N
in ch i: InChI=1S/C13H15IN6S/c14-9-5-7-10(8-6-9)15-16-12-17-18-13(21)20(12)19-11-3-1-2-4-11/h1,3,5-8,11,15,19H,2,4H2,(H,16,17)(H,18,21)
comment: Compound 16 is reported as an inhibitor of the helicase function of nsp13 of MERS-CoV, and was designed as a potential inhibitor of viral replication <Reference id=39403/>. It would be interesting to determine if this activity extends to the SARS-CoV-2 helicase nsp12.
iupac name: 4-(cyclopent-1-en-3-ylamino)-5-(2-(4-iodophenyl)hydrazinyl)-4H-1,2,4-triazole-3-thiol
approved: f
ligand name: compound 16 [PMID: 31955138]
type: SyntheticOrganicLigand

coumamycin
in ch i key: WTIJXIZOODAMJT-DHFGXMAYSA-N
in ch i: InChI=1S/C55H59N5O20/c1-21-12-16-29(57-21)48(67)77-42-38(63)52(79-54(6,7)44(42)71-10)73-31-18-14-26-36(61)34(50(69)75-40(26)24(31)4)59-46(65)28-20-56-33(23(28)3)47(66)60-35-37(62)27-15-19-32(25(5)41(27)76-51(35)70)74-53-39(64)43(45(72-11)55(8,9)80-53)78-49(68)30-17-13-22(2)58-30/h12-20,38-39,42-45,52-53,56-58,61-64H,1-11H3,(H,59,65)(H,60,66)/t38-,39-,42+,43+,44-,45-,52-,53-/m1/s1
comment: Coumamycin is an antibacterial compound, that inhibits bacterial topoisomerase activity <Reference id=39390/><Reference id=39391/>, and which has activity against Gram-positive bacteria.
iupac name: [(3R,4S,5R,6R)-5-hydroxy-6-[4-hydroxy-3-[[5-[[4-hydroxy-7-[(2R,3R,4S,5R)-3-hydroxy-5-methoxy-6,6-dimethyl-4-(5-methyl-1H-pyrrole-2-carbonyl)oxyoxan-2-yl]oxy-8-methyl-2-oxochromen-3-yl]carbamoyl]-4-methyl-1H-pyrrole-3-carbonyl]amino]-8-methyl-2-oxochromen-7-yl]oxy-3-methoxy-2,2-dimethyloxan-4-yl] 5-methyl-1H-pyrrole-2-carboxylate
synonym: coumermycin A1
synonym: notomycin
approved: f
ligand name: coumamycin
type: SyntheticOrganicLigand

telithromycin
in ch i key: LJVAJPDWBABPEJ-XZVSULPPSA-N
in ch i: InChI=1S/C43H65N5O10/c1-12-33-43(8)37(48(41(53)58-43)19-14-13-18-47-23-31(45-24-47)30-16-15-17-44-22-30)27(4)34(49)25(2)21-42(7,54-11)38(28(5)35(50)29(6)39(52)56-33)57-40-36(51)32(46(9)10)20-26(3)55-40/h15-17,22-29,32-33,36-38,40,51H,12-14,18-21H2,1-11H3/t25-,26-,27+,28+,29-,32+,33-,36-,37+,38-,40+,42-,43-/m1/s1
comment: Telithromycin is a ketolide antibacterial <Reference id=39387/><Reference id=39388/><Reference id=39389/>.
iupac name: (1S,2R,5R,7R,8R,9R,11R,13R,14S)-8-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-2-ethyl-9-methoxy-1,5,7,9,11,13-hexamethyl-15-[4-(4-pyridin-3-ylimidazol-1-yl)butyl]-3,17-dioxa-15-azabicyclo[12.3.0]heptadecane-4,6,12,16-tetrone
synonym: Ketek®
synonym: Levviax®
synonym: RU 66647
synonym: RU-66647
synonym: RU66647
synonym: HMR-3647
approved: t
ligand name: telithromycin
type: SyntheticOrganicLigand

tomopenem
in ch i key: KEDAXBWZURNCHS-GPODMPQUSA-N
comment: Tomopenem is a carbapenem antibacterial <Reference id=39365/><Reference id=39366/><Reference id=39368/>. It was reported to exhibit enhanced in vitro activity against oxacillin-resistant Staphylococci and Pseudomonas aeruginosa <Reference id=39369/>.
iupac name: (4R,5S,6S)-3-[(3S,5S)-5-[(3S)-3-[[2-(diaminomethylideneamino)acetyl]amino]pyrrolidine-1-carbonyl]-1-methylpyrrolidin-3-yl]sulfanyl-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
xref: CHEMBL389847
synonym: CS-023
synonym: R-115685
synonym: R115685
synonym: CS023
synonym: RO-4908463
approved: f
ligand name: tomopenem
type: SyntheticOrganicLigand

pafuramidine
canonical SMILES: CO/N=C(/c1ccc(cc1)c1ccc(o1)c1ccc(cc1)/C(=N/OC)/N)/N
isomeric SMILES: CO/N=C(/c1ccc(cc1)c1ccc(o1)c1ccc(cc1)/C(=N/OC)/N)/N
in ch i key: UKOQVLAXCBRRGH-UHFFFAOYSA-N
in ch i: InChI=1S/C20H20N4O3/c1-25-23-19(21)15-7-3-13(4-8-15)17-11-12-18(27-17)14-5-9-16(10-6-14)20(22)24-26-2/h3-12H,1-2H3,(H2,21,23)(H2,22,24)
comment: Pafuramidine (DB-289) is a prodrug which generates the active moiety DB-75 which exhibits antiprotozoal and antifungal activities <Reference id=39306/>. It is a pentamidine-related dicationic molecule. Mechanistically, the drug binds to the minor groove of DNA. It has activity against parasites and also Mycobacterium tuberculosis.
iupac name: N'-methoxy-4-[5-[4-[(Z)-N'-methoxycarbamimidoyl]phenyl]furan-2-yl]benzenecarboximidamide
xref: CHEMBL319669
synonym: DB-289
synonym: DB289
approved: f
ligand name: pafuramidine
type: SyntheticOrganicLigand

oritavancin
in ch i key: VHFGEBVPHAGQPI-LXKZPTCJSA-N
comment: Oritavancin is a semi-synthetic glycopeptide antibacterial drug <Reference id=39385/>. It is structurally related to vancomycin, and likewise is active against several Gram-positive organisms including methicillin resistant Staphylococcus aureus (MRSA). Like <Ligand id=10876/>, it offers the option of single-dose administration.
xref: CHEMBL1688530
synonym: Orbactiv®
synonym: LY333328
synonym: LY-333328
synonym: Kimyrsa®
approved: t
ligand name: oritavancin
type: SyntheticOrganicLigand

dalbavancin
in ch i key: KGPGQDLTDHGEGT-VBZOGQDBSA-N
comment: Dalbavancin is a second-generation, semi-synthetic lipoglycopeptide antibacterial <Reference id=39382/><Reference id=39383/>. It has been modified to increase activity and allow once-weekly dosing. Dalbavancin inhibits cross-linking of bacterial cell wall peptidoglycans, and thereby disrupts bacterial cell wall synthesis. It has little activity against Gram-negative bacilli <Reference id=39384/>.
synonym: Dalvance®
synonym: Xydalba®
synonym: BI-397
synonym: BI397
synonym: BI 397
approved: t
ligand name: dalbavancin
type: SyntheticOrganicLigand

zoliflodacin
in ch i key: ZSWMIFNWDQEXDT-ZESJGQACSA-N
in ch i: InChI=1S/C22H22FN5O7/c1-8-7-33-21(32)28(8)17-12-4-11-5-22(18(29)24-20(31)25-19(22)30)16-10(3)34-9(2)6-27(16)14(11)13(23)15(12)35-26-17/h4,8-10,16H,5-7H2,1-3H3,(H2,24,25,29,30,31)/t8-,9+,10-,16+/m0/s1
comment: Zoliflodacin is an antibacterial that inhibits bacterial DNA gyrase and topoisomerave IV.
xref: CHEMBL3544978
synonym: AZD-0914
synonym: AZD0914
synonym: EXT0914
synonym: EXT-0914
approved: f
ligand name: zoliflodacin
type: SyntheticOrganicLigand

zidebactam
in ch i key: YCZPXRQPDCXTIO-BBBLOLIVSA-N
in ch i: InChI=1S/C13H21N5O7S/c19-11(8-2-1-5-14-6-8)15-16-12(20)10-4-3-9-7-17(10)13(21)18(9)25-26(22,23)24/h8-10,14H,1-7H2,(H,15,19)(H,16,20)(H,22,23,24)/t8-,9-,10+/m1/s1
comment: Zidebactam (WCK 5107) is a novel β-lactamase inhibitor <Reference id=39379/><Reference id=39380/>. It was developed for the treatment of serious infections caused by highly drug-resistant Gram-negative pathogens.
iupac name: [(2S,5R)-7-oxo-2-[[[(3R)-piperidine-3-carbonyl]amino]carbamoyl]-1,6-diazabicyclo[3.2.1]octan-6-yl] hydrogen sulfate
synonym: WCK-5107
synonym: WCK 5107
synonym: WCK5107
approved: f
ligand name: zidebactam
type: SyntheticOrganicLigand

zabofloxacin
in ch i key: ZNPOCLHDJCAZAH-UCQKPKSFSA-N
in ch i: InChI=1S/C19H20FN5O4/c1-29-23-14-6-24(9-19(14)7-21-8-19)17-13(20)4-11-15(26)12(18(27)28)5-25(10-2-3-10)16(11)22-17/h4-5,10,21H,2-3,6-9H2,1H3,(H,27,28)/b23-14-
comment: Zabofloxacin is a fluoroquinolone antibacterial that inhibits type II and type IV topoisomerases <Reference id=39378/>. It has activity against Gram-positive bacteria and against Gram-negative Neisseria gonorrhoeae, including strains that are resistant to other quinolone antibacterials.
iupac name: 1-cyclopropyl-6-fluoro-7-[(8E)-8-methoxyimino-2,6-diazaspiro[3.4]octan-6-yl]-4-oxo-1,8-naphthyridine-3-carboxylic acid
synonym: DW-224a
approved: f
ligand name: zabofloxacin
type: SyntheticOrganicLigand

lenapenem
in ch i key: PZLOCBSBEUDCPF-YJIVIRPOSA-N
comment: Lenapenem (BO-2727) is a parenteral carbapenem class antibacterial <Reference id=39269/><Reference id=39271/>. It is active against methicillin-resistant staphylococci and has antipseudomonal activity <Reference id=39270/>.
iupac name: (4R,5S,6S)-6-[(1R)-1-hydroxyethyl]-3-[(3S,5S)-5-[(1R)-1-hydroxy-3-(methylamino)propyl]pyrrolidin-3-yl]sulfanyl-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
xref: CHEMBL3989459
synonym: BO-2727
synonym: BO2727
synonym: L-739,428
synonym: L-739428
approved: f
ligand name: lenapenem
type: SyntheticOrganicLigand

viquidacin
in ch i key: USGHRRVFKSLEJT-WVBUVRCRSA-N
comment: Viquidacin acts as an inhibitor of bacterial topoisomerse IV and DNA gyrase (topoisomerase II) <Reference id=39377/>.
iupac name: (3R,4R)-4-[(3S)-3-(3-fluoro-6-methoxyquinolin-4-yl)-3-hydroxypropyl]-1-(2-thiophen-2-ylsulfanylethyl)piperidine-3-carboxylic acid
xref: CHEMBL2158050
synonym: NXL101
synonym: AVE4221
synonym: AVE-4221
synonym: NXL-101
synonym: compound 1 [PMID: 23968485]
approved: f
ligand name: viquidacin
type: SyntheticOrganicLigand

trospectomycin
in ch i key: KHAUBYTYGDOYRU-IRXASZMISA-N
in ch i: InChI=1S/C17H30N2O7/c1-4-5-6-8-7-9(20)17(23)16(24-8)25-15-13(22)10(18-2)12(21)11(19-3)14(15)26-17/h8,10-16,18-19,21-23H,4-7H2,1-3H3/t8-,10-,11+,12+,13+,14-,15-,16+,17+/m1/s1
comment: Trospectomycin is an aminocyclitol. It inhibits the protein synthesis function of the bacterial 30S ribosomal subunit <Reference id=39372/><Reference id=39373/>.
xref: CHEMBL1614655
synonym: U-63,366F
synonym: U-63366F
synonym: U63366F
approved: f
ligand name: trospectomycin
type: SyntheticOrganicLigand

sanfetrinem
in ch i key: ICFDDEJRXZSWTA-KJFVXYAMSA-N
in ch i: InChI=1S/C14H19NO5/c1-6(16)9-11-7-4-3-5-8(20-2)10(7)12(14(18)19)15(11)13(9)17/h6-9,11,16H,3-5H2,1-2H3,(H,18,19)/t6-,7+,8+,9-,11-/m1/s1
comment: Sanfetrinem is a β-lactam antibacterial that has activity against Gram-positive and Gram-negative bacteria <Reference id=39332/>. The compound is available as the prodrug sanfetrinem cilexetil (GV 104326)
iupac name: (1S,5S,8aS,8bR)-1-[(1R)-1-hydroxyethyl]-5-methoxy-2-oxo-5,6,7,8,8a,8b-hexahydro-1H-azeto[1,2-b]isoindole-4-carboxylic acid
xref: CHEMBL316197
synonym: GV118819
synonym: GV-118819
synonym: GV-118819X
approved: f
ligand name: sanfetrinem
type: SyntheticOrganicLigand

timcodar
in ch i key: MQSMWZHHUGSULF-QNGWXLTQSA-N
in ch i: InChI=1S/C43H45ClN4O6/c1-47(43(51)40(49)34-27-38(52-2)41(54-4)39(28-34)53-3)37(26-32-10-14-35(44)15-11-32)42(50)48(29-33-8-6-5-7-9-33)36(16-12-30-18-22-45-23-19-30)17-13-31-20-24-46-25-21-31/h5-11,14-15,18-25,27-28,36-37H,12-13,16-17,26,29H2,1-4H3/t37-/m0/s1
comment: Timcodar (VX-853) is a pyridine compound that was developed by Vertex Pharmaceuticals. It acts as a mammalian and bacterial efflux pump inhibitor. It was proposed to enhance activity of antibacterials such as rifampin, by inhibiting their efflux via bacterial efflux pumps <Reference id=39362/><Reference id=39364/>. It was also investigated for potential to prevent efflux of chemotherapy drugs, to enhance cancer treatment, and has been proposed as a possible antiobesity therapy <Reference id=39363/>.
xref: CHEMBL2059028
synonym: VX-853
synonym: VX853
approved: f
ligand name: timcodar
type: SyntheticOrganicLigand

tigemonam
canonical SMILES: OC(=O)CO/N=C(/c1csc(n1)N)/C(=O)N[C@@H]1C(=O)N(C1(C)C)OS(=O)(=O)O
isomeric SMILES: OC(=O)CO/N=C(/c1csc(n1)N)/C(=O)N[C@@H]1C(=O)N(C1(C)C)OS(=O)(=O)O
in ch i key: VAMSVIZLXJOLHZ-QWFSEIHXSA-N
in ch i: InChI=1S/C12H15N5O9S2/c1-12(2)8(10(21)17(12)26-28(22,23)24)15-9(20)7(16-25-3-6(18)19)5-4-27-11(13)14-5/h4,8H,3H2,1-2H3,(H2,13,14)(H,15,20)(H,18,19)(H,22,23,24)/b16-7-/t8-/m1/s1
comment: Tigemonam is a monobactam antibacterial <Reference id=39359/><Reference id=39360/>. It has Gram-positive activity, and is stable against β-lactamases, but has no activity against Psedomonas. SQ-30836 (tigemonam dicholate) is an orally absorbed salt of tigemonam <Reference id=39361/>.
iupac name: 2-[(Z)-[1-(2-amino-1,3-thiazol-4-yl)-2-[[(3S)-2,2-dimethyl-4-oxo-1-sulfooxyazetidin-3-yl]amino]-2-oxoethylidene]amino]oxyacetic acid
synonym: SQ-30213
synonym: SQ30213
synonym: SQ-30836 (tigemonam dicholate)
synonym: SQ30836 (tigemonam dicholate)
approved: f
ligand name: tigemonam
type: SyntheticOrganicLigand

temafloxacin
in ch i key: QKDHBVNJCZBTMR-UHFFFAOYSA-N
in ch i: InChI=1S/C21H18F3N3O3/c1-11-9-26(5-4-25-11)19-8-18-13(7-16(19)24)20(28)14(21(29)30)10-27(18)17-3-2-12(22)6-15(17)23/h2-3,6-8,10-11,25H,4-5,9H2,1H3,(H,29,30)
comment: Temafloxacin (A-62254) is a fluoroquinolone antibacterial <Reference id=39346/>.
iupac name: 1-(2,4-difluorophenyl)-6-fluoro-7-(3-methylpiperazin-1-yl)-4-oxoquinoline-3-carboxylic acid
xref: CHEMBL277100
synonym: A-62254
synonym: A62254
synonym: Abbott 62254
synonym: Omniflox®
approved: t
ligand name: temafloxacin
type: SyntheticOrganicLigand

tedizolid
in ch i key: XFALPSLJIHVRKE-GFCCVEGCSA-N
in ch i: InChI=1S/C17H15FN6O3/c1-23-21-16(20-22-23)15-5-2-10(7-19-15)13-4-3-11(6-14(13)18)24-8-12(9-25)27-17(24)26/h2-7,12,25H,8-9H2,1H3/t12-/m1/s1
comment: Tedizolid is an oxazolidinone antiobiotic <Reference id=39357/>.
iupac name: (5R)-3-[3-fluoro-4-[6-(2-methyltetrazol-5-yl)pyridin-3-yl]phenyl]-5-(hydroxymethyl)-1,3-oxazolidin-2-one
xref: CHEMBL1257051
synonym: TR-700
synonym: TR700
synonym: Sivextro®
synonym: previously torezolid
synonym: DA-7157
approved: t
ligand name: tedizolid
type: SyntheticOrganicLigand

tebipenem pivoxil
in ch i key: SNUDIPVBUUXCDG-QHSBEEBCSA-N
in ch i: InChI=1S/C22H31N3O6S2/c1-11-15-14(12(2)26)18(27)25(15)16(19(28)30-10-31-20(29)22(3,4)5)17(11)33-13-8-24(9-13)21-23-6-7-32-21/h11-15,26H,6-10H2,1-5H3/t11-,12-,14-,15-/m1/s1
comment: Tebipenem pivoxil is an orally available pivaloyloxymethyl ester prodrug of the β-lactam antibacterial tebipenem <Reference id=39355/><Reference id=39354/>. The ester bond is cleaved, releasing active tebipenem (PubChem CID 9800194; LJC-11036). The drug has Gram-negative activity. Tebipenem pivoxil hydrobromide (SPR994) is another formulation of the same drug.
iupac name: 2,2-dimethylpropanoyloxymethyl (4R,5S,6S)-3-[1-(4,5-dihydro-1,3-thiazol-2-yl)azetidin-3-yl]sulfanyl-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate
synonym: L-084
synonym: LJC 11,084
synonym: LJC-11,084
synonym: LJC-11084
synonym: Orapenem®
synonym: TBPM-PI
approved: t
ligand name: tebipenem pivoxil
type: SyntheticOrganicLigand

tacapenem
in ch i key: CTEFNVKDRWMZSL-CTNSIQBBSA-N
comment: Tacapenem (R-95867) is a β-lactam class antibacterial. It exhibits broad-spectrum antibacterial activity and it is highly stable to β-lactamases. An ester-type prodrug of R-95867, CS-834 (tacapenem pivoxil for oral administration), has been described <Reference id=39352/>.
iupac name: (4R,5S,6S)-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-3-[(3R)-5-oxopyrrolidin-3-yl]sulfanyl-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
xref: CHEMBL3989499
synonym: R95867
synonym: R-95867
approved: f
ligand name: tacapenem
type: SyntheticOrganicLigand

sulopenem
in ch i key: FLSUCZWOEMTFAQ-PRBGKLEPSA-N
in ch i: InChI=1S/C12H15NO5S3/c1-5(14)7-9(15)13-8(11(16)17)12(20-10(7)13)19-6-2-3-21(18)4-6/h5-7,10,14H,2-4H2,1H3,(H,16,17)/t5-,6+,7+,10-,21-/m1/s1
comment: Sulopenem is a β-lactam (carbapenem) antibacterial <Reference id=39350/>. It has a broad-spectrum of activity against Gram-negative, Gram-positive and anaerobic bacteria, including multi-drug resistant Gram-negative infections in both the hospital and community settings. Sulopenem is relatively stable against hydrolysis by various β-lactamases. It is being developed for oral and parenteral administration.
iupac name: (5R,6S)-6-[(1R)-1-hydroxyethyl]-7-oxo-3-[(1R,3S)-1-oxothiolan-3-yl]sulfanyl-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
xref: CHEMBL1908305
synonym: CP-70429
synonym: CP70429
synonym: CP-70,429
approved: f
ligand name: sulopenem
type: SyntheticOrganicLigand

squalamine
in ch i key: UIRKNQLZZXALBI-MSVGPLKSSA-N
in ch i: InChI=1S/C34H65N3O5S/c1-23(2)31(42-43(39,40)41)12-9-24(3)27-10-11-28-32-29(14-16-34(27,28)5)33(4)15-13-26(21-25(33)22-30(32)38)37-20-8-19-36-18-7-6-17-35/h23-32,36-38H,6-22,35H2,1-5H3,(H,39,40,41)/t24-,25-,26+,27-,28+,29+,30-,31-,32+,33+,34-/m1/s1
comment: Squalamine was examined for antibacterial activity against Gram-positive and Gram-negative bacteria <Reference id=39347/><Reference id=39348/>, but development was discontinued at Phase 2.
iupac name: [(3R,6R)-6-[(3S,5R,7R,8R,9S,10S,13R,14S,17R)-3-[3-(4-aminobutylamino)propylamino]-7-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-methylheptan-3-yl] hydrogen sulfate
xref: CHEMBL444929
synonym: MSI-1256F (squalamine lactate)
synonym: 7alpha-Hydroxy, 3beta-spermidine
approved: f
ligand name: squalamine
type: SyntheticOrganicLigand

sparfloxacin
in ch i key: DZZWHBIBMUVIIW-DTORHVGOSA-N
in ch i: InChI=1S/C19H22F2N4O3/c1-8-5-24(6-9(2)23-8)17-13(20)15(22)12-16(14(17)21)25(10-3-4-10)7-11(18(12)26)19(27)28/h7-10,23H,3-6,22H2,1-2H3,(H,27,28)/t8-,9+
comment: Sparfloxacin is a fluoroquinolone antibacterial. It has a less than ideal side-effect profile <Reference id=39827/> that led to its withdrawl from the US market.
iupac name: 5-amino-1-cyclopropyl-7-[(3R,5S)-3,5-dimethylpiperazin-1-yl]-6,8-difluoro-4-oxoquinoline-3-carboxylic acid
xref: CHEMBL850
synonym: SPFX
synonym: AT-4140
synonym: AT4140
synonym: CI-978
synonym: CI978
synonym: Zagam ®
approved: t
ligand name: sparfloxacin
type: SyntheticOrganicLigand

pirbenicillin
in ch i key: WRFCGBVLTRJBKN-QSNWEANLSA-N
in ch i: InChI=1S/C24H26N6O5S/c1-24(2)18(23(34)35)30-21(33)17(22(30)36-24)29-20(32)16(13-6-4-3-5-7-13)28-15(31)12-27-19(25)14-8-10-26-11-9-14/h3-11,16-18,22H,12H2,1-2H3,(H2,25,27)(H,28,31)(H,29,32)(H,34,35)/t16-,17-,18+,22-/m1/s1
comment: Pirbenicillin is a semisynthetic penicillin with antibacterial activity against Gram-positive and Gram-negative bacteria <Reference id=39311/>.
iupac name: (2S,5R,6R)-6-[[(2R)-2-[[2-[[amino(pyridin-4-yl)methylidene]amino]acetyl]amino]-2-phenylacetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
xref: CHEMBL2110979
synonym: CP-33,994-2
synonym: CP-33,994
approved: f
ligand name: pirbenicillin
type: SyntheticOrganicLigand

solithromycin
in ch i key: IXXFZUPTQVDPPK-ZAWHAJPISA-N
in ch i: InChI=1S/C43H65FN6O10/c1-12-32-43(8)35(50(40(55)60-43)19-14-13-18-49-23-30(46-47-49)28-16-15-17-29(45)21-28)26(4)33(51)24(2)22-41(6,56-11)37(27(5)36(53)42(7,44)39(54)58-32)59-38-34(52)31(48(9)10)20-25(3)57-38/h15-17,21,23-27,31-32,34-35,37-38,52H,12-14,18-20,22,45H2,1-11H3/t24-,25-,26+,27+,31+,32-,34-,35-,37-,38+,41-,42+,43-/m1/s1
comment: Solithromycin is a next-generation oral and intravenous fluoroketolide (macrolide) antibacterial that has activity against Gram-positive and Gram-negative bacteria <Reference id=39342/>.
iupac name: (1S,2R,5S,7R,8R,9R,11R,13R,14R)-15-[4-[4-(3-aminophenyl)triazol-1-yl]butyl]-8-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-2-ethyl-5-fluoro-9-methoxy-1,5,7,9,11,13-hexamethyl-3,17-dioxa-15-azabicyclo[12.3.0]heptadecane-4,6,12,16-tetrone
xref: CHEMBL1232510
synonym: Solithera
synonym: T4288
synonym: T-4288
synonym: CEM-101
synonym: CEM101
synonym: OP-1068
synonym: OP1068
synonym: compound 3 [PMID: 30258539]
approved: f
ligand name: solithromycin
type: SyntheticOrganicLigand

sarafloxacin
in ch i key: XBHBWNFJWIASRO-UHFFFAOYSA-N
in ch i: InChI=1S/C20H17F2N3O3/c21-12-1-3-13(4-2-12)25-11-15(20(27)28)19(26)14-9-16(22)18(10-17(14)25)24-7-5-23-6-8-24/h1-4,9-11,23H,5-8H2,(H,27,28)
comment: Sarafloxacin (A-56620) is a quinolone antibacterial <Reference id=39335/><Reference id=39336/><Reference id=39337/>.
iupac name: 6-fluoro-1-(4-fluorophenyl)-4-oxo-7-piperazin-1-ylquinoline-3-carboxylic acid
xref: CHEMBL37858
synonym: A-56620
synonym: A56620
approved: t
ligand name: sarafloxacin
type: SyntheticOrganicLigand

mesdopetam
canonical SMILES: CCCNCCOc1cc(F)cc(c1)S(=O)(=O)C
isomeric SMILES: CCCNCCOc1cc(F)cc(c1)S(=O)(=O)C
in ch i key: OSBPYFBXSLJHCR-UHFFFAOYSA-N
in ch i: InChI=1S/C12H18FNO3S/c1-3-4-14-5-6-17-11-7-10(13)8-12(9-11)18(2,15)16/h7-9,14H,3-6H2,1-2H3
comment: Mesdopetam (IRL790) is an experimental small molecule compound with psychomotor stabilizing properties. The primary target is the dopamine D3 receptor, a target implicated in the generation of levodopa-induced dyskinesia, a side-effect frequently occurring with long-term levodopa treatment in patients with Parkinson's disease.
iupac name: N-[2-(3-fluoro-5-methylsulfonylphenoxy)ethyl]propan-1-amine
synonym: IRL790
approved: f
ligand name: mesdopetam
type: SyntheticOrganicLigand

rosaramicin
in ch i key: IUPCWCLVECYZRV-JZMZINANSA-N
in ch i: InChI=1S/C31H51NO9/c1-9-25-20(5)29-31(6,41-29)12-10-23(34)17(2)14-21(11-13-33)28(19(4)24(35)16-26(36)39-25)40-30-27(37)22(32(7)8)15-18(3)38-30/h10,12-13,17-22,24-25,27-30,35,37H,9,11,14-16H2,1-8H3/b12-10+/t17-,18-,19+,20-,21+,22+,24-,25-,27-,28-,29+,30+,31+/m1/s1
comment: Rosaramicin is a macrolide antibacterial. It has activity against Neisseria gonorrhoeae, Chlamydia trachomatis, Ureaplasma urealyticum and Mycoplasma hominis.
iupac name: 2-[(1S,2R,3R,7R,8S,9S,10R,12R,14E,16S)-9-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-3-ethyl-7-hydroxy-2,8,12,16-tetramethyl-5,13-dioxo-4,17-dioxabicyclo[14.1.0]heptadec-14-en-10-yl]acetaldehyde
xref: CHEMBL8965
synonym: rosamicin
synonym: SCH-14947
synonym: SCH14947
synonym: Antibiotic 67-694
synonym: Antibiotic 67694
approved: f
ligand name: rosaramicin
type: SyntheticOrganicLigand

ritipenem
in ch i key: IKQNRQOUOZJHTR-UWBRJAPDSA-N
in ch i: InChI=1S/C10H12N2O6S/c1-3(13)5-7(14)12-6(9(15)16)4(19-8(5)12)2-18-10(11)17/h3,5,8,13H,2H2,1H3,(H2,11,17)(H,15,16)/t3-,5+,8-/m1/s1
comment: Ritipenem (FCE 22101) exhibits broad-spectrum bacteriolytic activity <Reference id=39327/><Reference id=39328/>. Its activity profile is similar to that of imipenem, but it shows no activity against Pseudomonas aeruginosa. It is delivered as the orally bioavailable prodrug ritipenem acoxyl (Penemac®, FCE-22891).
iupac name: (5R,6S)-3-(carbamoyloxymethyl)-6-[(1R)-1-hydroxyethyl]-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
xref: CHEMBL70088
synonym: FCE22101
synonym: FCE-22101
approved: f
ligand name: ritipenem
type: SyntheticOrganicLigand

relebactam
in ch i key: SMOBCLHAZXOKDQ-ZJUUUORDSA-N
in ch i: InChI=1S/C12H20N4O6S/c17-11(14-8-3-5-13-6-4-8)10-2-1-9-7-15(10)12(18)16(9)22-23(19,20)21/h8-10,13H,1-7H2,(H,14,17)(H,19,20,21)/t9-,10+/m1/s1
comment: Relebactam is a β-lactamase inhibitor <Reference id=39320/>.
iupac name: [(2S,5R)-7-oxo-2-(piperidin-4-ylcarbamoyl)-1,6-diazabicyclo[3.2.1]octan-6-yl] hydrogen sulfate
xref: CHEMBL3112741
synonym: MK-7655
synonym: MK7655
synonym: MK-7655A
approved: t
ligand name: relebactam
type: SyntheticOrganicLigand

razupenem
in ch i key: XFGOMLIRJYURLQ-GOKYHWASSA-N
in ch i: InChI=1S/C18H21N3O4S2/c1-7-4-10(5-19-7)11-6-26-18(20-11)27-15-8(2)13-12(9(3)22)16(23)21(13)14(15)17(24)25/h4,6-9,12-13,19,22H,5H2,1-3H3,(H,24,25)/t7-,8+,9+,12+,13+/m0/s1
comment: Razupenem is a penem class antibacterial. It inhibits cell wall synthesis, and is active against Gram-negative and Gram-positive bacteria <Reference id=39317/><Reference id=39318/><Reference id=39319/>.
iupac name: (4R,5S,6S)-6-[(1R)-1-hydroxyethyl]-4-methyl-3-[[4-[(5S)-5-methyl-2,5-dihydro-1H-pyrrol-3-yl]-1,3-thiazol-2-yl]sulfanyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
xref: CHEMBL1256722
synonym: SMP-601
synonym: SM-216601
synonym: PZ-601
approved: f
ligand name: razupenem
type: SyntheticOrganicLigand

ranimycin
in ch i key: HEWICEWYFOOYNG-OHBODLIOSA-N
in ch i: InChI=1S/C12H18O6/c1-6(2)3-9(15)18-12-7(5-13)4-8(14)10(16)11(12)17/h4-6,8,10-12,14,16-17H,3H2,1-2H3/t8-,10-,11+,12+/m0/s1
comment: Ranimycin is a lincosamide antibacterial, that was derived from a variant of Streptomyces lincolnensis.
iupac name: [(1R,4S,5S,6R)-2-formyl-4,5,6-trihydroxycyclohex-2-en-1-yl] 3-methylbutanoate
synonym: U-25873
synonym: Rancomycin 2
synonym: U-25,873
approved: f
ligand name: ranimycin
type: SyntheticOrganicLigand

radezolid
in ch i key: BTTNOGHPGJANSW-IBGZPJMESA-N
in ch i: InChI=1S/C22H23FN6O3/c1-14(30)25-12-19-13-29(22(31)32-19)18-6-7-20(21(23)8-18)16-4-2-15(3-5-16)9-24-10-17-11-26-28-27-17/h2-8,11,19,24H,9-10,12-13H2,1H3,(H,25,30)(H,26,27,28)/t19-/m0/s1
comment: Radezolid (RX-1741) is an oxazolidinone class antibacterial. It has activity against Gram-positive and Gram-negative bacteria.
iupac name: N-[[(5S)-3-[3-fluoro-4-[4-[(2H-triazol-4-ylmethylamino)methyl]phenyl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide
xref: CHEMBL455461
synonym: RX-1741
synonym: RX1741
synonym: RX-103
synonym: RX103
synonym: Rx-01_667
approved: f
ligand name: radezolid
type: SyntheticOrganicLigand

premafloxacin
in ch i key: SUQUWONDIBHQOZ-NWDGAFQWSA-N
in ch i: InChI=1S/C21H26FN3O4/c1-11(23-2)12-6-7-24(9-12)18-16(22)8-14-17(20(18)29-3)25(13-4-5-13)10-15(19(14)26)21(27)28/h8,10-13,23H,4-7,9H2,1-3H3,(H,27,28)/t11-,12+/m0/s1
comment: Premafloxacin is a fluoroquinolone antibacterial with activity against Gram-positive abd Gram-negactive pathogens <Reference id=39314/>.
iupac name: 1-cyclopropyl-6-fluoro-8-methoxy-7-[(3R)-3-[(1S)-1-(methylamino)ethyl]pyrrolidin-1-yl]-4-oxoquinoline-3-carboxylic acid
xref: CHEMBL230599
synonym: U95376
synonym: U-95376
synonym: compound 21 [PMID: 17303420]
approved: f
ligand name: premafloxacin
type: SyntheticOrganicLigand

plazomicin
in ch i key: IYDYFVUFSPQPPV-PEXOCOHZSA-N
in ch i: InChI=1S/C25H48N6O10/c1-25(37)11-38-24(18(35)21(25)29-2)41-20-15(31-22(36)16(33)5-6-26)9-14(28)19(17(20)34)40-23-13(27)4-3-12(39-23)10-30-7-8-32/h3,13-21,23-24,29-30,32-35,37H,4-11,26-28H2,1-2H3,(H,31,36)/t13-,14+,15-,16+,17+,18-,19-,20+,21-,23-,24-,25+/m1/s1
comment: Plazomicin is a semisynthetic derivative of <Ligand id=10858/> and belongs to the aminoglycoside class of antibacterial compounds <Reference id=44094/>.
iupac name: (2S)-4-amino-N-[(1R,2S,3S,4R,5S)-5-amino-4-[[(2S,3R)-3-amino-6-[(2-hydroxyethylamino)methyl]-3,4-dihydro-2H-pyran-2-yl]oxy]-2-[(2R,3R,4R,5R)-3,5-dihydroxy-5-methyl-4-(methylamino)oxan-2-yl]oxy-3-hydroxycyclohexyl]-2-hydroxybutanamide
xref: CHEMBL1650559
synonym: ACHN-490
synonym: ACHN490
synonym: Zemdri®
approved: t
ligand name: plazomicin
type: SyntheticOrganicLigand

A2315A
canonical SMILES: O=C1NC/C=C/C(=C/C(O)CC(O)Cc2nc(C(=O)NC(C(=O)OC(C(/C=C/1)C)C(C)C)C)co2)/C
isomeric SMILES: O=C1NC/C=C/C(=C/C(O)CC(O)Cc2nc(C(=O)NC(C(=O)OC(C(/C=C/1)C)C(C)C)C)co2)/C
in ch i key: SAQNYTQFLPVTNJ-JYXGQRMOSA-N
in ch i: InChI=1S/C26H37N3O7/c1-15(2)24-17(4)8-9-22(32)27-10-6-7-16(3)11-19(30)12-20(31)13-23-29-21(14-35-23)25(33)28-18(5)26(34)36-24/h6-9,11,14-15,17-20,24,30-31H,10,12-13H2,1-5H3,(H,27,32)(H,28,33)/b7-6+,9-8+,16-11+
comment: A2315 (plauracin) is a new member of the virginiamycin family of antibacterials. Physical and chemical data indicate that it is related to ostreogrycin A. The INN record states that plauracin is a complex, isolated from Actinoplanes auranticolor ATCC 31011, allocates CAS registry number 62107-94-2, but does not provide a chemical structure. A proposed chemical structure for one component (A2315A) is presented in <Reference id=39313/>, which generates the SMILES string used here. This maps to PubChem CID 10368807. The structure of the other component is unclear.
approved: f
ligand name: A2315A
type: SyntheticOrganicLigand

pirazmonam
in ch i key: JXSPWQGYERHATM-MUXKCCDJSA-N
comment: Pirazmonam ia a siderophore monobactam type antibacterial, with activity against Gram-negative pathogens <Reference id=39310/>.
iupac name: 2-[(Z)-[1-(2-amino-1,3-thiazol-4-yl)-2-[[1-[[3-[(5-hydroxy-4-oxo-1H-pyridine-2-carbonyl)amino]-2-oxoimidazolidin-1-yl]sulfonylcarbamoyl]-2-oxoazetidin-3-yl]amino]-2-oxoethylidene]amino]oxy-2-methylpropanoic acid
xref: CHEMBL2110757
synonym: SQ-83360
synonym: SQ83360
synonym: compound 2 [PMID: 25658376]
synonym: SQ 83,360
approved: f
ligand name: pirazmonam
type: SyntheticOrganicLigand

fludalanine
canonical SMILES: [C@]([2H])(C(=O)O)(CF)N
isomeric SMILES: [C@]([2H])(C(=O)O)(CF)N
in ch i key: UYTSRQMXRROFPU-LIIDHCAMSA-N
in ch i: InChI=1S/C3H6FNO2/c4-1-2(5)3(6)7/h2H,1,5H2,(H,6,7)/t2-/m1/s1/i2D
comment: Fludalanine is a small alanine derivative that acts as bacterial cell wall component mimetic and antibacterial.
iupac name: (2S)-2-amino-2-deuterio-3-fluoropropanoic acid
xref: CHEMBL2107426
synonym: 3-fluoro-D-alanine
synonym: MK-0642
synonym: MK0642
approved: f
ligand name: fludalanine
type: SyntheticOrganicLigand

penicillamine
canonical SMILES: NC(C(S)(C)C)C(=O)O
isomeric SMILES: N[C@H](C(S)(C)C)C(=O)O
in ch i key: VVNCNSJFMMFHPL-VKHMYHEASA-N
in ch i: InChI=1S/C5H11NO2S/c1-5(2,9)3(6)4(7)8/h3,9H,6H2,1-2H3,(H,7,8)/t3-/m0/s1
comment: Penicillamine is a chelating agent and an immunosuppressant.
iupac name: (2S)-2-amino-3-methyl-3-sulfanylbutanoic acid
xref: CHEMBL1430
synonym: Depen
synonym: Trolovol
synonym: D Penicillamine
synonym: D Mercaptovaline
synonym: Cuprimine®
approved: t
ligand name: penicillamine
type: SyntheticOrganicLigand

paldimycin
in ch i key: VSHJMNNDPYEUOT-ILYCIZJESA-N
comment: Paldimycin is a mixture of Paldimycins A (CAS 94555-00-7; CID 139597408) and B (CAS 94555-01-8; CID 139597428) which are also known as U-67963 and U-67964 which were derived from paulomycins A and B. It acts as a protein synthesis inhibitor. Paldimycin exhibited good antibacterial activity against Gram-positiive pathogens <Reference id=39308/><Reference id=39309/>.
iupac name: (3S)-3-[5-[3-[(2R)-2-acetamido-2-carboxyethyl]sulfanyl-2-[[(2R)-2-acetamido-2-carboxyethyl]sulfanylcarbothioylamino]butanoyl]oxy-6-(acetyloxymethyl)-3-hydroxy-4-[5-hydroxy-4-methoxy-6-methyl-5-[(1S)-1-[(2S)-2-methylbutanoyl]oxyethyl]oxan-2-yl]oxyoxan-2-yl]-2,3-dihydroxy-6-imino-5-oxocyclohexene-1-carboxylic acid;(3S)-3-[5-[3-[(2R)-2-acetamido-2-carboxyethyl]sulfanyl-2-[[(2R)-2-acetamido-2-carboxyethyl]sulfanylcarbothioylamino]butanoyl]oxy-6-(acetyloxymethyl)-3-hydroxy-4-[5-hydroxy-4-methoxy-6-methyl-5-[(1S)-1-(2-methylpropanoyloxy)ethyl]oxan-2-yl]oxyoxan-2-yl]-2,3-dihydroxy-6-imino-5-oxocyclohexene-1-carboxylic acid
synonym: Antibiotic 273 A
synonym: U-70,138
synonym: U-70138F
approved: f
ligand name: paldimycin
type: SyntheticOrganicLigand

ozenoxacin
in ch i key: XPIJWUTXQAGSLK-UHFFFAOYSA-N
in ch i: InChI=1S/C21H21N3O3/c1-11-8-13(9-23-20(11)22-3)15-6-7-16-18(12(15)2)24(14-4-5-14)10-17(19(16)25)21(26)27/h6-10,14H,4-5H2,1-3H3,(H,22,23)(H,26,27)
comment: Ozenoxacin is a non-fluorinated quinolone antibacterial.
iupac name: 1-cyclopropyl-8-methyl-7-[5-methyl-6-(methylamino)pyridin-3-yl]-4-oxoquinoline-3-carboxylic acid
xref: CHEMBL3990047
synonym: Xepi®
synonym: Ozadub®
synonym: T-3912
synonym: T3912
approved: t
ligand name: ozenoxacin
type: SyntheticOrganicLigand

oxantel
canonical SMILES: Oc1cccc(c1)/C=C/C1=NCCCN1C
isomeric SMILES: Oc1cccc(c1)/C=C/C1=NCCCN1C
in ch i key: VRYKTHBAWRESFI-VOTSOKGWSA-N
in ch i: InChI=1S/C13H16N2O/c1-15-9-3-8-14-13(15)7-6-11-4-2-5-12(16)10-11/h2,4-7,10,16H,3,8-9H2,1H3/b7-6+
comment: Oxantel is an anthelmintic agent. In addition, it inhibits fumarate reductase, an enzyme that is crucial for the survival of pathogenic bacteria in the biofilm in periodontal pockets. It has been suggested that oxantel might guard against chronic periodontitis, but efficacy of this potential antibacterial function is yet to be confirmed <Reference id=39303/><Reference id=39304/>.
iupac name: 3-[(E)-2-(1-methyl-5,6-dihydro-4H-pyrimidin-2-yl)ethenyl]phenol
xref: CHEMBL1240977
synonym: CP-14,445
synonym: CP-14445
approved: t
ligand name: oxantel
type: SyntheticOrganicLigand

omadacycline
in ch i key: VJYKVCURWJGLPG-IQZGDKDPSA-N
in ch i: InChI=1S/C29H40N4O7/c1-28(2,3)12-31-11-14-10-17(32(4)5)15-8-13-9-16-21(33(6)7)24(36)20(27(30)39)26(38)29(16,40)25(37)18(13)23(35)19(15)22(14)34/h10,13,16,21,31,34-35,38,40H,8-9,11-12H2,1-7H3,(H2,30,39)/t13-,16-,21-,29-/m0/s1
comment: Omadacycline (PTK-0796) is an oral, tetracycline-like antibacterial <Reference id=39301/>.
iupac name: (4S,4aS,5aR,12aR)-4,7-bis(dimethylamino)-9-[(2,2-dimethylpropylamino)methyl]-1,10,11,12a-tetrahydroxy-3,12-dioxo-4a,5,5a,6-tetrahydro-4H-tetracene-2-carboxamide
xref: CHEMBL1689772
synonym: PTK-0796
synonym: PTK0796
synonym: Nuzyra®
synonym: compound 6 [PMID: 21302930]
synonym: amadacycline
approved: t
ligand name: omadacycline
type: SyntheticOrganicLigand

olamufloxacin
in ch i key: LEILBPMISZFZQK-GFCCVEGCSA-N
in ch i: InChI=1S/C20H23FN4O3/c1-9-16-13(18(26)11(19(27)28)6-25(16)10-2-3-10)15(23)14(21)17(9)24-7-12(22)20(8-24)4-5-20/h6,10,12H,2-5,7-8,22-23H2,1H3,(H,27,28)/t12-/m1/s1
comment: Olamufloxacin (HSR-903) is a low toxicity synthetic fluoroquinolone antibacterial agent <Reference id=39299/><Reference id=39298/><Reference id=39300/>. It inhibits supercoiling by Escherichia coli DNA gyrase, but it is much less active against human topoisomerase II <Reference id=39298/>.
iupac name: 5-amino-7-[(7S)-7-amino-5-azaspiro[2.4]heptan-5-yl]-1-cyclopropyl-6-fluoro-8-methyl-4-oxoquinoline-3-carboxylic acid
xref: CHEMBL2078925
synonym: HSR-903
synonym: HSR903
approved: f
ligand name: olamufloxacin
type: SyntheticOrganicLigand

nifurprazine
canonical SMILES: Nc1ccc(nn1)/C=C/c1ccc(o1)[N+](=O)[O-]
isomeric SMILES: Nc1ccc(nn1)/C=C/c1ccc(o1)[N+](=O)[O-]
in ch i key: XDWLRMBWIWKFNC-HNQUOIGGSA-N
in ch i: InChI=1S/C10H8N4O3/c11-9-5-2-7(12-13-9)1-3-8-4-6-10(17-8)14(15)16/h1-6H,(H2,11,13)/b3-1+
comment: Nifurprazine is an antimicrobial nitrofuran drug. It may have trypanocidal activity <Reference id=39296/>.
iupac name: 6-[(E)-2-(5-nitrofuran-2-yl)ethenyl]pyridazin-3-amine
xref: CHEMBL2105219
synonym: HB115
synonym: HB-115
synonym: carofur
approved: f
ligand name: nifurprazine
type: SyntheticOrganicLigand

nemonoxacin
in ch i key: AVPQPGFLVZTJOR-RYUDHWBXSA-N
in ch i: InChI=1S/C20H25N3O4/c1-11-7-12(21)9-22(8-11)16-6-5-14-17(19(16)27-2)23(13-3-4-13)10-15(18(14)24)20(25)26/h5-6,10-13H,3-4,7-9,21H2,1-2H3,(H,25,26)/t11-,12-/m0/s1
comment: Nemonoxacin is a non-fluorinated quinolone antibacterial with broad-spectrum activity against Gram-positive and Gram-negative bacteria and atypical pathogens, including methicillin-resistant S. aureus (MRSA) and vancomycin-resistant pathogens <Reference id=39293/><Reference id=39294/>. It selectively inhibits bacterial DNA topoisomerase (DNA gyrase) activity.
iupac name: 7-[(3S,5S)-3-amino-5-methylpiperidin-1-yl]-1-cyclopropyl-8-methoxy-4-oxoquinoline-3-carboxylic acid
xref: CHEMBL1213456
synonym: TG-873870
synonym: TG873870
synonym: Taigexyn®
approved: t
ligand name: nemonoxacin
type: SyntheticOrganicLigand

narasin
in ch i key: VHKXXVVRRDYCIK-CWCPJSEDSA-N
in ch i: InChI=1S/C43H72O11/c1-12-30(35(46)27(8)34(45)28(9)36-23(4)21-24(5)37(51-36)31(13-2)39(47)48)38-25(6)22-26(7)42(52-38)18-15-32(44)43(54-42)20-19-40(11,53-43)33-16-17-41(49,14-3)29(10)50-33/h15,18,23-34,36-38,44-45,49H,12-14,16-17,19-22H2,1-11H3,(H,47,48)/t23-,24-,25-,26+,27-,28-,29-,30-,31+,32+,33+,34+,36+,37+,38-,40-,41+,42-,43-/m0/s1
comment: Narasin is an anti-protozoal agent with activity against Coccidia parasites (e.g. Toxoplasma gondii). It also has limited antibacterial activity against Gram +ve bacteria.
xref: CHEMBL2104423
synonym: C-7819B
synonym: Narasin A
synonym: Lilly 79891
synonym: Monteban®
approved: f
ligand name: narasin
type: SyntheticOrganicLigand

linezolid
in ch i key: TYZROVQLWOKYKF-ZDUSSCGKSA-N
in ch i: InChI=1S/C16H20FN3O4/c1-11(21)18-9-13-10-20(16(22)24-13)12-2-3-15(14(17)8-12)19-4-6-23-7-5-19/h2-3,8,13H,4-7,9-10H2,1H3,(H,18,21)/t13-/m0/s1
comment: Linezolid is a synthetic oxazolidinone class antibacterial with activity against Gram-positive pathogens <Reference id=39272/>. It also has activity as a MAO (monoamine oxidase) inhibitor.
iupac name: N-[[(5S)-3-(3-fluoro-4-morpholin-4-ylphenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide
xref: CHEMBL126
synonym: ZLD
synonym: Zyvox®
synonym: PNU-100766
synonym: PNU100766
synonym: U-100766
synonym: U-100,766
approved: t
ligand name: linezolid
type: SyntheticOrganicLigand

avibactam
in ch i key: NDCUAPJVLWFHHB-UHNVWZDZSA-N
in ch i: InChI=1S/C7H11N3O6S/c8-6(11)5-2-1-4-3-9(5)7(12)10(4)16-17(13,14)15/h4-5H,1-3H2,(H2,8,11)(H,13,14,15)/t4-,5+/m1/s1
comment: Avibactam (NXL104) is non-β-lactam β-lactamase inhibitor <Reference id=39143/>. It has activity against class A and C serine β-lactamases, including Klebsiella pneumoniae carbapenemases.
iupac name: [(2S,5R)-2-carbamoyl-7-oxo-1,6-diazabicyclo[3.2.1]octan-6-yl] hydrogen sulfate
xref: CHEMBL1689063
synonym: NXL104
synonym: NXL-104
synonym: NXL 104
synonym: AVI
approved: t
ligand name: avibactam
type: SyntheticOrganicLigand

nafithromycin
in ch i key: RLFCSBSRGRJFRO-QAOQTAGDSA-N
in ch i: InChI=1S/C42H62N6O11S/c1-13-28-42(9)30(29(39(53)58-42)35(43)47-59-25(7)36-45-46-37(60-36)26-16-14-15-17-44-26)22(4)31(49)20(2)19-41(8,54-12)34(23(5)32(50)24(6)38(52)56-28)57-40-33(51)27(48(10)11)18-21(3)55-40/h14-17,20-25,27-30,33-34,40,51H,13,18-19H2,1-12H3,(H2,43,47)/t20-,21-,22-,23+,24-,25+,27+,28-,29-,30+,33-,34-,40+,41-,42-/m1/s1
comment: Nafithromycin (WCK-4873) is a ketolide antibacterial with Gram-positive activity <Reference id=39290/><Reference id=39291/>.
iupac name: (1S,2R,5R,7R,8R,9R,11R,13R,14S,15R)-8-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-2-ethyl-9-methoxy-1,5,7,9,11,13-hexamethyl-4,6,12,16-tetraoxo-N'-[(1S)-1-(5-pyridin-2-yl-1,3,4-thiadiazol-2-yl)ethoxy]-3,17-dioxabicyclo[12.3.0]heptadecane-15-carboximidamide
xref: CHEMBL4297519
synonym: WCK 4873
synonym: WCK-4873
synonym: WCK4873
approved: f
ligand name: nafithromycin
type: SyntheticOrganicLigand

finafloxacin
in ch i key: FYMHQCNFKNMJAV-HOTGVXAUSA-N
in ch i: InChI=1S/C20H19FN4O4/c21-14-5-11-17(25(10-1-2-10)7-13(19(11)26)20(27)28)12(6-22)18(14)24-8-15-16(9-24)29-4-3-23-15/h5,7,10,15-16,23H,1-4,8-9H2,(H,27,28)/t15-,16-/m0/s1
comment: Finafloxacin is a fluoroquinolone antibacterial.
iupac name: 7-[(4aS,7aS)-3,4,4a,5,7,7a-hexahydro-2H-pyrrolo[3,4-b][1,4]oxazin-6-yl]-8-cyano-1-cyclopropyl-6-fluoro-4-oxoquinoline-3-carboxylic acid
xref: CHEMBL1908370
synonym: Xtoro®
synonym: AL-60371
synonym: AL60371
approved: f
ligand name: finafloxacin
type: SyntheticOrganicLigand

contezolid acefosamil (parent)
in ch i key: YCRAGJLWFBGKFE-CYBMUJFWSA-N
comment: Contezolid acefosamil is delivered as the sodium salt, which is represented by PubChem CID 131750213. We show the structure for the parent molecule here. The active moiety <Ligand id=10795/> acts as a potent oxazolidinone antibacterial against Gram-positive pathogens <Reference id=39211/>.
xref: CHEMBL4301914
synonym: MRX-4
approved: f
ligand name: contezolid acefosamil (parent)
type: SyntheticOrganicLigand

contezolid
in ch i key: SULYVXZZUMRQAX-NSHDSACASA-N
in ch i: InChI=1S/C18H15F3N4O4/c19-12-7-13(15(20)16(21)17(12)24-4-1-10(26)2-5-24)25-9-11(29-18(25)27)8-22-14-3-6-28-23-14/h1,3-4,6-7,11H,2,5,8-9H2,(H,22,23)/t11-/m0/s1
comment: Contezolid is an oxazolidinone antibacterial against Gram-positive pathogens <Reference id=39211/>, including methicillin-resistant Staphylococcus aureus (MRSA), penicillin-resistant Streptococcus pneumoniae, penicillin-intermediate S. pneumoniae (PISP), and vancomycin-resistant enterococci (VRE). Its orally delivered prodrug is <Ligand id=10796/> (MRX-4). Contezolid targets protein synthesis by binding to the V region of the bacterial 23S rRNA.
iupac name: (5S)-5-[(1,2-oxazol-3-ylamino)methyl]-3-[2,3,5-trifluoro-4-(4-oxo-2,3-dihydropyridin-1-yl)phenyl]-1,3-oxazolidin-2-one
xref: CHEMBL3287379
synonym: MRX-1
synonym: MRX-I
synonym: Youxitai®
approved: t
ligand name: contezolid
type: SyntheticOrganicLigand

metformin
canonical SMILES: CN(C(=N)N=C(N)N)C
isomeric SMILES: CN(C(=N)N=C(N)N)C
in ch i key: XZWYZXLIPXDOLR-UHFFFAOYSA-N
in ch i: InChI=1S/C4H11N5/c1-9(2)4(7)8-3(5)6/h1-2H3,(H5,5,6,7,8)
comment: Marketed formulations contain metformin hydrochloride (PubChem CID 14219). Metformin is often given in fixed-dose combinations with other antihyperglycemic agents. Repurposing: Cancer cells undergo a metabolic switch to aerobic glycolysis, and become reliant on this metabolic pathway for energy (the Warburg effect). Inhibition of the glycolytic pathway is therefore considered as a tractable therapeutic target in oncology. As metformin is an inhibitor of glycolysis it is being examined for anti-cancer effects in a number of malignancies. Similarly, it is being examined for anti-inflammatory potential since activated immune cells also undergo a metabolic switch to aerobic glycolysis. If found to be effective, this could ultimately lead to metformin being repurposed for indications other than type 2 diabetes.
iupac name: 1-[(diaminomethylidene)amino]-N,N-dimethylmethanimidamide
xref: CHEMBL1431
synonym: Apo-Metformin
synonym: Fortamet
synonym: Gen-Metformin
synonym: Glucophage XR
synonym: Glumetza
synonym: Glycon
synonym: Mylan-Metformin
synonym: Novo-Metformin
synonym: Nu-Metformin
synonym: PMS-Metformin
synonym: Ran-Metformin
synonym: Ratio-Metformin
synonym: Riomet
synonym: Sandoz Metformin
synonym: Teva-Metformin
synonym: Glucophage®
synonym: LA-6023
approved: t
ligand name: metformin
type: SyntheticOrganicLigand

murepavadin
in ch i key: RIDRXGOBXZLKHZ-NZUANIILSA-N
comment: Murepavadin is a cyclic β hairpin peptidomimetic based on the cationic antimicrobial peptide protegrin I. It targets the outer membrane of Gram-negative pathogens <Reference id=39284/>.
xref: CHEMBL3946483
synonym: RG7929
synonym: POL7080
synonym: RG-7929
synonym: RO-7033877
synonym: RO7033877
approved: f
ligand name: murepavadin
type: PeptideLigand

minocycline
in ch i key: FFTVPQUHLQBXQZ-KVUCHLLUSA-N
in ch i: InChI=1S/C23H27N3O7/c1-25(2)12-5-6-13(27)15-10(12)7-9-8-11-17(26(3)4)19(29)16(22(24)32)21(31)23(11,33)20(30)14(9)18(15)28/h5-6,9,11,17,27-28,31,33H,7-8H2,1-4H3,(H2,24,32)/t9-,11-,17-,23-/m0/s1
comment: Minocycline is a tetracycline antibacterial that has activity against Gram-negative and Gram-positive bacteria.
iupac name: (4S,4aS,5aR,12aR)-4,7-bis(dimethylamino)-1,10,11,12a-tetrahydroxy-3,12-dioxo-4a,5,5a,6-tetrahydro-4H-tetracene-2-carboxamide
synonym: MINO
synonym: CL 59806
synonym: CL59806
synonym: CL-59806
synonym: NSC-141993
synonym: Dynacin®
synonym: Minocin®
approved: t
ligand name: minocycline
type: SyntheticOrganicLigand

mideplanin
in ch i key: KVZUWEFUEGGULL-UHFFFAOYSA-N
comment: Mideplanin is an experimental glycopeptide antibacterial, that is a semisynthetic amide derivative of teicoplanin <Reference id=39278/>.
synonym: CTA A1
synonym: MDL 62873
synonym: MDL62873
synonym: MDL-62873
approved: f
ligand name: mideplanin
type: PeptideLigand

meropenem
in ch i key: DMJNNHOOLUXYBV-PQTSNVLCSA-N
comment: Meropenem is a parenterally delivered, broad-spectrum carbapenem antibacterial. It is active against Gram-positive and Gram-negative bacteria, and is effective against aerobic and anaerobic pathogens including Klebsiella, E. coli, Enterococcus, Clostridium spp.
iupac name: (4R,5S,6S)-3-[(3S,5S)-5-(dimethylcarbamoyl)pyrrolidin-3-yl]sulfanyl-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
xref: CHEMBL127
synonym: Merrem®
synonym: ICI 194,660
synonym: SM-7338
approved: t
ligand name: meropenem
type: SyntheticOrganicLigand

maridomycin
in ch i key: FFXJTOKFQATYBI-BUHFOSPRSA-N
in ch i: InChI=1S/C41H67NO16/c1-11-30(45)55-29-19-32(47)51-22(4)18-28-27(54-28)14-13-26(44)21(3)17-25(15-16-43)37(38(29)50-10)58-40-35(48)34(42(8)9)36(23(5)53-40)57-33-20-41(7,49)39(24(6)52-33)56-31(46)12-2/h13-14,16,21-29,33-40,44,48-49H,11-12,15,17-20H2,1-10H3/b14-13+
comment: Maridomycin is an experimental macrolide antibacterial <Reference id=39275/><Reference id=39276/> that was developed by Takeda.
synonym: Maridomycin III
synonym: LS-87912
approved: f
ligand name: maridomycin
type: SyntheticOrganicLigand

FK-881
canonical SMILES: COc1ccc(cc1)n1nc(nc1c1ccc(cc1)OC)OC
isomeric SMILES: COc1ccc(cc1)n1nc(nc1c1ccc(cc1)OC)OC
in ch i key: OBAICMYWONZOSZ-UHFFFAOYSA-N
in ch i: InChI=1S/C17H17N3O3/c1-21-14-8-4-12(5-9-14)16-18-17(23-3)19-20(16)13-6-10-15(22-2)11-7-13/h4-11H,1-3H3
comment: FK-881 (ASP6537) is a selective COX-1 inhibitor <Reference id=37049/>.
iupac name: 3-methoxy-1,5-bis(4-methoxyphenyl)-1,2,4-triazole
xref: CHEMBL3427203
synonym: ASP6537
synonym: ASP-6537
synonym: FK881
approved: f
ligand name: FK-881
type: SyntheticOrganicLigand

lefamulin
in ch i key: KPVIXBKIJXZQJX-FCEONZPQSA-N
in ch i: InChI=1S/C28H45NO5S/c1-6-26(4)14-22(34-23(32)15-35-21-8-7-18(29)13-20(21)31)27(5)16(2)9-11-28(17(3)25(26)33)12-10-19(30)24(27)28/h6,16-18,20-22,24-25,31,33H,1,7-15,29H2,2-5H3/t16-,17+,18-,20-,21-,22-,24+,25+,26-,27+,28+/m1/s1
comment: Lefamulin (BC-3781) is a pleuromutilin class antibacterial <Reference id=39264/><Reference id=39267/>. It is active against pathogens that commonly cause community-acquired bacterial pneumonia (CABP) and acute bacterial skin and skin structure infection (ABSSSI) <Reference id=39266/>.
xref: CHEMBL3291398
synonym: BC-3781
synonym: BC3781
synonym: Xenleta®
synonym: compound 7 [PMID: 24874438]
approved: t
ligand name: lefamulin
type: SyntheticOrganicLigand

lascufloxacin
in ch i key: ZFIOCUITTUUVPV-MEDUHNTESA-N
in ch i: InChI=1S/C21H24F3N3O4/c1-31-20-17-13(19(28)14(21(29)30)9-26(17)5-4-22)6-15(23)18(20)27-8-11(16(24)10-27)7-25-12-2-3-12/h6,9,11-12,16,25H,2-5,7-8,10H2,1H3,(H,29,30)/t11-,16+/m0/s1
comment: Lascufloxacin (KRP-AM1977Y) is an investigational intravenous fluoroquinolone antiobiotic that was developed for lower respiratory tract infections <Reference id=39263/>. It is effective against both aerobic and anaerobic bacteria, and is highly distributed in the lung.
iupac name: 7-[(3S,4S)-3-[(cyclopropylamino)methyl]-4-fluoropyrrolidin-1-yl]-6-fluoro-1-(2-fluoroethyl)-8-methoxy-4-oxoquinoline-3-carboxylic acid
synonym: KRP-AM1977
approved: f
ligand name: lascufloxacin
type: SyntheticOrganicLigand

tolfenamic acid
canonical SMILES: OC(=O)c1ccccc1Nc1cccc(c1C)Cl
isomeric SMILES: OC(=O)c1ccccc1Nc1cccc(c1C)Cl
in ch i key: YEZNLOUZAIOMLT-UHFFFAOYSA-N
in ch i: InChI=1S/C14H12ClNO2/c1-9-11(15)6-4-8-12(9)16-13-7-3-2-5-10(13)14(17)18/h2-8,16H,1H3,(H,17,18)
comment: Tolfenamic acid is a non-steroidal anti-inflammatory drug (NSAID) with analgesic, antipyretic and anti-inflammatory actions <Reference id=29822/>.
iupac name: 2-[(3-chloro-2-methylphenyl)amino]benzoic acid
xref: CHEMBL121626
synonym: Clotam®
approved: t
ligand name: tolfenamic acid
type: SyntheticOrganicLigand

iseganan
in ch i key: GUCYBPFJNGVFEB-XELKFLSISA-N
comment: Iseganan is a synthetic protegrin peptide with bactericidal, fungicidal and antiendotoxin activities <Reference id=39261/><Reference id=39262/>.
xref: CHEMBL2110753
synonym: IB-367-03
synonym: IB-367
approved: f
ligand name: iseganan
type: PeptideLigand

imipenem
in ch i key: ZSKVGTPCRGIANV-ZXFLCMHBSA-N
in ch i: InChI=1S/C12H17N3O4S/c1-6(16)9-7-4-8(20-3-2-14-5-13)10(12(18)19)15(7)11(9)17/h5-7,9,16H,2-4H2,1H3,(H2,13,14)(H,18,19)/t6-,7-,9-/m1/s1
comment: Imipenem is a broad-spectrum, semi-synthetic, intravenous β-lactam carbapenem derived from thienamycin.
iupac name: (5R,6S)-3-[2-(aminomethylideneamino)ethylsulfanyl]-6-[(1R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
xref: CHEMBL148
synonym: MK 0787
synonym: MK0787
synonym: MK-0787
synonym: Primaxin® (imipenem + cilastatin)
synonym: Recarbrio® (imipenem + cilastatin + relebactam).
approved: t
ligand name: imipenem
type: SyntheticOrganicLigand

ibafloxacin
canonical SMILES: OC(=O)c1cn2C(C)CCc3c2c(c1=O)cc(c3C)F
isomeric SMILES: OC(=O)c1cn2C(C)CCc3c2c(c1=O)cc(c3C)F
in ch i key: DXKRGNXUIRKXNR-UHFFFAOYSA-N
in ch i: InChI=1S/C15H14FNO3/c1-7-3-4-9-8(2)12(16)5-10-13(9)17(7)6-11(14(10)18)15(19)20/h5-7H,3-4H2,1-2H3,(H,19,20)
comment: Ibafloxacin is a quinolone antibacterial with activity against Gram -ve and Gram +ve pathogens <Reference id=39253/>. It was not progressed to clinical evaluation in humans.
xref: CHEMBL170052
synonym: S-25930
synonym: S25930
synonym: R-835
synonym: R835
approved: f
ligand name: ibafloxacin
type: SyntheticOrganicLigand

grepafloxacin
in ch i key: AIJTTZAVMXIJGM-UHFFFAOYSA-N
in ch i: InChI=1S/C19H22FN3O3/c1-10-8-22(6-5-21-10)15-7-14-16(11(2)17(15)20)18(24)13(19(25)26)9-23(14)12-3-4-12/h7,9-10,12,21H,3-6,8H2,1-2H3,(H,25,26)
comment: Grepafloxacin is a quinolone antibacterial <Reference id=39251/><Reference id=39252/>.
iupac name: 1-cyclopropyl-6-fluoro-5-methyl-7-(3-methylpiperazin-1-yl)-4-oxoquinoline-3-carboxylic acid
xref: CHEMBL583
synonym: OPC 17116
synonym: OPC17116
synonym: OPC-17116
synonym: Raxar®
approved: t
ligand name: grepafloxacin
type: SyntheticOrganicLigand

gepotidacin
in ch i key: PZFAZQUREQIODZ-LJQANCHMSA-N
in ch i: InChI=1S/C24H28N6O3/c31-22-4-3-20-24-29(22)15-19(30(24)23(32)13-27-20)14-28-7-5-17(6-8-28)25-11-18-10-16-2-1-9-33-21(16)12-26-18/h3-4,10,12-13,17,19,25H,1-2,5-9,11,14-15H2/t19-/m1/s1
comment: Gepotidacin (formerly GSK2140944) is a novel, first-in-class, triazaacenaphthylene antibacterial that inhibits bacterial DNA gyrase and topoisomerase IV via a unique mechanism <Reference id=39247/><Reference id=39250/>. It was developed for potential to treat conventional and biothreat pathogens including MRSA, respiratory tract infections, acute bacterial skin and skin structure infections (ABSSI) <Reference id=39249/>, and uncomplicated urogenital gonorrhea <Reference id=39248/>.
iupac name: (3R)-3-[[4-(3,4-dihydro-2H-pyrano[2,3-c]pyridin-6-ylmethylamino)piperidin-1-yl]methyl]-1,4,7-triazatricyclo[6.3.1.04,12]dodeca-6,8(12),9-triene-5,11-dione
xref: CHEMBL3317856
synonym: GSK2140944
synonym: GSK-2140944
approved: f
ligand name: gepotidacin
type: SyntheticOrganicLigand

gatifloxacin
in ch i key: XUBOMFCQGDBHNK-UHFFFAOYSA-N
in ch i: InChI=1S/C19H22FN3O4/c1-10-8-22(6-5-21-10)16-14(20)7-12-15(18(16)27-2)23(11-3-4-11)9-13(17(12)24)19(25)26/h7,9-11,21H,3-6,8H2,1-2H3,(H,25,26)
comment: Gatifloxacin is a synthetic fourth-generation fluoroquinolone antibacterial with broad-spectrum activity against Gram-negative and Gram-positive pathogens.
iupac name: 1-cyclopropyl-6-fluoro-8-methoxy-7-(3-methylpiperazin-1-yl)-4-oxoquinoline-3-carboxylic acid
synonym: Tequin®
synonym: Zymar®
synonym: Gatiflo®
synonym: AM-1155
synonym: AM1155
synonym: GTFX
approved: t
ligand name: gatifloxacin
type: SyntheticOrganicLigand

fusidic acid
in ch i key: IECPWNUMDGFDKC-MZJAQBGESA-N
in ch i: InChI=1S/C31H48O6/c1-17(2)9-8-10-20(28(35)36)26-22-15-24(34)27-29(5)13-12-23(33)18(3)21(29)11-14-30(27,6)31(22,7)16-25(26)37-19(4)32/h9,18,21-25,27,33-34H,8,10-16H2,1-7H3,(H,35,36)/b26-20-/t18-,21-,22-,23+,24+,25-,27-,29-,30-,31-/m0/s1
comment: Fusidic acid is an orally bioavailable fusidane antibacterial with activity against Gram +ve pathogens <Reference id=39245/><Reference id=39246/>.
iupac name: (2Z)-2-[(3R,4S,5S,8S,9S,10S,11R,13R,14S,16S)-16-acetyloxy-3,11-dihydroxy-4,8,10,14-tetramethyl-2,3,4,5,6,7,9,11,12,13,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-17-ylidene]-6-methylhept-5-enoic acid
xref: CHEMBL374975
synonym: CEM-102
synonym: CEM102
synonym: Taksta®
synonym: fusidate
synonym: sodium fusidate
synonym: Fucidin®
approved: t
ligand name: fusidic acid
type: SyntheticOrganicLigand

furazolium
canonical SMILES: [O-][N+](=O)c1ccc(o1)c1csc2=NCCn12
isomeric SMILES: [O-][N+](=O)c1ccc(o1)c1csc2=NCCn12
in ch i key: QWNNGDMXFGRSPJ-UHFFFAOYSA-N
in ch i: InChI=1S/C9H7N3O3S/c13-12(14)8-2-1-7(15-8)6-5-16-9-10-3-4-11(6)9/h1-2,5H,3-4H2
comment: We show the structure of the parent molecule here. The INN represents the chloride salt form (NF-963, CAS number 5118-17-2) <Reference id=39242/>. Furazolium is a nitrofuran-derivative with antibacterial activity against Gram +ve and Gram -ve pathogens <Reference id=40473/>. It was developed by Eaton Laboratories in the late 1960s and was tested against skin infections, but never reached clinical approval.
iupac name: 3-(5-nitrofuran-2-yl)-5,6-dihydroimidazo[2,1-b][1,3]thiazole
xref: CHEMBL2110940
synonym: Novofur
approved: f
ligand name: furazolium
type: SyntheticOrganicLigand

fosfomycin
canonical SMILES: C[C@@H]1O[C@@H]1P(=O)(O)O
isomeric SMILES: C[C@@H]1O[C@@H]1P(=O)(O)O
in ch i key: YMDXZJFXQJVXBF-STHAYSLISA-N
in ch i: InChI=1S/C3H7O4P/c1-2-3(7-2)8(4,5)6/h2-3H,1H3,(H2,4,5,6)/t2-,3+/m0/s1
comment: Fosfomycin is a phosphonic acid antibacterial, with broad antibacterial activity against Gram +ve and Gram -ve pathogens <Reference id=39240/>. It was originally isolated from certain types of Streptomyces, but it is now made synthetically.
iupac name: [(2R,3S)-3-methyloxiran-2-yl]phosphonic acid
xref: CHEMBL1757
synonym: phosphomycin
synonym: phosphonomycin
synonym: Veramina®
synonym: Monurol®
approved: t
ligand name: fosfomycin
type: SyntheticOrganicLigand

HSK3486
canonical SMILES: C[C@@H](c1cccc(c1O)C(C)C)C1CC1
isomeric SMILES: C[C@@H](c1cccc(c1O)C(C)C)C1CC1
in ch i key: BMEARIQHWSVDBS-SNVBAGLBSA-N
in ch i: InChI=1S/C14H20O/c1-9(2)12-5-4-6-13(14(12)15)10(3)11-7-8-11/h4-6,9-11,15H,7-8H2,1-3H3/t10-/m1/s1
comment: A short-acting, potent GABAA receptor agonist.
iupac name: 2-[(1R)-1-cyclopropylethyl]-6-propan-2-ylphenol
xref: CHEMBL4094894
synonym: HSK-3486
synonym: HSK 3486
approved: f
ligand name: HSK3486
type: SyntheticOrganicLigand

fandofloxacin
in ch i key: AWCAUUQZTXYMPB-UHFFFAOYSA-N
in ch i: InChI=1S/C20H18F2N4O3/c1-24-4-6-25(7-5-24)17-9-16-13(8-15(17)22)19(27)14(20(28)29)11-26(16)18-3-2-12(21)10-23-18/h2-3,8-11H,4-7H2,1H3,(H,28,29)
comment: Fandofloxacin (DW-116) is an oral fluoroquinolone antibacterial <Reference id=39223/>.
iupac name: 6-fluoro-1-(5-fluoropyridin-2-yl)-7-(4-methylpiperazin-1-yl)-4-oxoquinoline-3-carboxylic acid
xref: CHEMBL2106560
synonym: DW-116
synonym: DW116
approved: f
ligand name: fandofloxacin
type: SyntheticOrganicLigand

clinafloxacin
in ch i key: QGPKADBNRMWEQR-UHFFFAOYSA-N
comment: Clinafloxacin is a fluoroquinalone antibacterial that inhibits bacterial DNA topoisomerase.
iupac name: 7-(3-aminopyrrolidin-1-yl)-8-chloro-1-cyclopropyl-6-fluoro-4-oxoquinoline-3-carboxylic acid
xref: CHEMBL278255
synonym: AM 1091
synonym: CI-960
synonym: PD-127321
synonym: PD 127321
approved: f
ligand name: clinafloxacin
type: SyntheticOrganicLigand

cetocycline
in ch i key: LUYXWZOOMKBUMB-ONJZCGHCSA-N
in ch i: InChI=1S/C22H21NO7/c1-7-4-5-10-8(2)11-6-12-16(23)19(27)13(9(3)24)20(28)22(12,30)21(29)15(11)18(26)14(10)17(7)25/h4-5,12,16,25-26,28,30H,6,23H2,1-3H3/t12-,16+,22+/m0/s1
comment: Cetocycline is an atypical tetracycline type antibacterial <Reference id=39206/><Reference id=39208/>. It is effective against tetracycline resistant bacteria suggesting that its mechanism of action is different to that of tetracycline <Reference id=39207/>.
iupac name: (1R,4aR,12aS)-3-acetyl-1-amino-4,4a,6,7-tetrahydroxy-8,11-dimethyl-12,12a-dihydro-1H-tetracene-2,5-dione
xref: CHEMBL2110884
synonym: Abbott 40728
synonym: A-40728
synonym: chelocardin
synonym: compound 1 [PMID: 379332]
approved: f
ligand name: cetocycline
type: SyntheticOrganicLigand

(R)-2h [PMID:19625189]
in ch i key: KLURSWGCQQKDCT-CQSZACIVSA-N
in ch i: InChI=1S/C23H18F3N3O2/c1-14(13-15-7-3-2-4-8-15)29-21(16-9-5-6-10-18(16)30)28-17-11-12-27-20(23(24,25)26)19(17)22(29)31/h2-12,14,30H,13H2,1H3/t14-/m1/s1
comment: Compound (R)-2h is an orally bioavailable, negative regulator of the calcium-sensing receptor (CaSR) <Reference id=38545/><Reference id=38591/>. (R)-2h is short-acting, and is predicted to produce a rapid and transient release of parathyroid hormone (PTH) and an associated bone anabolic response. Molecules like (R)-2h, which act as rapid/transient negative CaSR modulators are being explored for potential as novel agents to treat bone-loss diseases.
iupac name: (R)-2-(2-hydroxyphenyl)-3-(1-phenylpropan-2-yl)-5-(trifluoromethyl)pyrido[4,3-d]pyrimidin-4(3H)-one
xref: CHEMBL565122
synonym: Pfizer compound 1
approved: f
ligand name: (R)-2h [PMID:19625189]
type: SyntheticOrganicLigand

evernimicin
in ch i key: UPADRKHAIMTUCC-OWALTSPQSA-N
comment: Evernimicin (SCH 27899) is an aminoglycoside antibacterial. It inhibits bacterial protein synthesis and is active against a number of Gram-positive organisms including MRSS and MRSA.
iupac name: [(2R,3R,4R,6S)-6-[(2R,2'R,3'S,3aR,4R,4'R,6S,7S,7aR)-6-[(2S,3R,4R,5S,6R)-2-[(2R,3S,4S,5S,6S)-6-[(3aR,3'aS,4R,6'S,7R,7'R,7aS,7'aS)-7-(2,4-dihydroxy-6-methylbenzoyl)oxy-7'-hydroxyspiro[3a,6,7,7a-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4,2'-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran]-6'-yl]oxy-4-hydroxy-5-methoxy-2-(methoxymethyl)oxan-3-yl]oxy-3-hydroxy-5-methoxy-6-methyloxan-4-yl]oxy-4',7-dihydroxy-2',4,7a-trimethylspiro[3a,4,6,7-tetrahydro-[1,3]dioxolo[4,5-c]pyran-2,6'-oxane]-3'-yl]oxy-4-[(2S,4S,5R,6S)-5-methoxy-4,6-dimethyl-4-nitrooxan-2-yl]oxy-2-methyloxan-3-yl] 3,5-dichloro-4-hydroxy-2-methoxy-6-methylbenzoate
xref: CHEMBL263367
synonym: SCH 27899
synonym: SCH27899
synonym: SCH-27899
synonym: Ziracin®
approved: f
ligand name: evernimicin
type: SyntheticOrganicLigand

eravacycline
in ch i key: AKLMFDDQCHURPW-ISIOAQNYSA-N
in ch i: InChI=1S/C27H31FN4O8/c1-31(2)20-13-8-11-7-12-14(28)9-15(30-16(33)10-32-5-3-4-6-32)21(34)18(12)22(35)17(11)24(37)27(13,40)25(38)19(23(20)36)26(29)39/h9,11,13,20,34-35,38,40H,3-8,10H2,1-2H3,(H2,29,39)(H,30,33)/t11-,13-,20-,27-/m0/s1
comment: Eravacycline is a parenteral tetracycline antibacterial.
iupac name: (4S,4aS,5aR,12aR)-4-(dimethylamino)-7-fluoro-1,10,11,12a-tetrahydroxy-3,12-dioxo-9-[(2-pyrrolidin-1-ylacetyl)amino]-4a,5,5a,6-tetrahydro-4H-tetracene-2-carboxamide
xref: CHEMBL1951095
synonym: TP-434
synonym: TP434
synonym: Xerava®
synonym: compound 17j [PMID: 2148514]
approved: t
ligand name: eravacycline
type: SyntheticOrganicLigand

eperezolid
in ch i key: SIMWTRCFFSTNMG-AWEZNQCLSA-N
in ch i: InChI=1S/C18H23FN4O5/c1-12(25)20-9-14-10-23(18(27)28-14)13-2-3-16(15(19)8-13)21-4-6-22(7-5-21)17(26)11-24/h2-3,8,14,24H,4-7,9-11H2,1H3,(H,20,25)/t14-/m0/s1
comment: Eperezolid is a oxazolidinone antibacterial. It inhibits protein synthesis by blocking function of the bacterial 50S ribosomal subunit. Eperezolid is not as potent as <Ligand id=10827/>, which was the first oxazolidinone to be approved for clinical use.
iupac name: N-[[(5S)-3-[3-fluoro-4-[4-(2-hydroxyacetyl)piperazin-1-yl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide
xref: CHEMBL47955
synonym: comound 2 [PMID: 23584544]
synonym: U-100592
synonym: U100592
synonym: PNU-100592
synonym: PNU 100592
synonym: PNU100592
approved: f
ligand name: eperezolid
type: SyntheticOrganicLigand

ecenofloxacin
in ch i key: WNVIWAUAXKEKKF-PJFSTRORSA-N
in ch i: InChI=1S/C19H21FN4O3/c1-19-5-14(21)12(19)7-23(8-19)17-13(20)4-10-15(25)11(18(26)27)6-24(9-2-3-9)16(10)22-17/h4,6,9,12,14H,2-3,5,7-8,21H2,1H3,(H,26,27)/t12-,14-,19-/m0/s1
comment: Ecenofloxacin (CFC-222) is a novel fluoroquinolone antibacterial with potent antibacterial activities against Gram-positive, Gram-negative, and anaerobic organisms <Reference id=39215/>.
iupac name: 7-[(1R,5S,6S)-6-amino-1-methyl-3-azabicyclo[3.2.0]heptan-3-yl]-1-cyclopropyl-6-fluoro-4-oxo-1,8-naphthyridine-3-carboxylic acid
xref: CHEMBL2107637
synonym: CFC-222
synonym: CFC222
approved: f
ligand name: ecenofloxacin
type: SyntheticOrganicLigand

difloxacin
in ch i key: NOCJXYPHIIZEHN-UHFFFAOYSA-N
in ch i: InChI=1S/C21H19F2N3O3/c1-24-6-8-25(9-7-24)19-11-18-15(10-17(19)23)20(27)16(21(28)29)12-26(18)14-4-2-13(22)3-5-14/h2-5,10-12H,6-9H2,1H3,(H,28,29)
comment: Difloxacin is a second-generation, synthetic fluoroquinolone antibacterial. It has broad-spectrum activity against Gram +ve and Gram -ve bacteria.
iupac name: 6-fluoro-1-(4-fluorophenyl)-7-(4-methylpiperazin-1-yl)-4-oxoquinoline-3-carboxylic acid
xref: CHEMBL6259
synonym: A-56619
synonym: A 56619
synonym: Dicural®
approved: f
ligand name: difloxacin
type: SyntheticOrganicLigand

diacerein
in ch i key: TYNLGDBUJLVSMA-UHFFFAOYSA-N
in ch i: InChI=1S/C19H12O8/c1-8(20)26-13-5-3-4-11-15(13)18(23)16-12(17(11)22)6-10(19(24)25)7-14(16)27-9(2)21/h3-7H,1-2H3,(H,24,25)
comment: Diacerein is a prodrug which is metabolized to rhein. It has anti-inflammatory activity via antagonism of the interleukin-1 receptor. It is an anthraquinone type compound and growth-inhibitory effects of diacerein have been shown against various drug-resistant staphylococcal strains <Reference id=39213/>.
iupac name: 4,5-diacetyloxy-9,10-dioxoanthracene-2-carboxylic acid
xref: CHEMBL41286
synonym: Artrodar®
synonym: Fisiodar®
approved: t
ligand name: diacerein
type: SyntheticOrganicLigand

delafloxacin
in ch i key: DYDCPNMLZGFQTM-UHFFFAOYSA-N
comment: Delafloxacin is a fourth generation fluoroquinolone class antibacterial. It has a good spectum of activity against gram-positive bacteria and some atypical pathogens.
iupac name: 1-(6-amino-3,5-difluoropyridin-2-yl)-8-chloro-6-fluoro-7-(3-hydroxyazetidin-1-yl)-4-oxoquinoline-3-carboxylic acid
xref: CHEMBL2105637
synonym: Baxdela®
synonym: ABT-492
synonym: ABT492
synonym: Abbott 492
synonym: Quofenix®
approved: t
ligand name: delafloxacin
type: SyntheticOrganicLigand

quinupristin
in ch i key: WTHRRGMBUAHGNI-LCYNINFDSA-N
in ch i: InChI=1S/C53H67N9O10S/c1-6-37-50(68)61-23-11-14-38(61)51(69)59(5)40(26-32-16-18-36(19-17-32)58(3)4)52(70)62-28-35(30-73-43-29-60-24-20-33(43)21-25-60)42(64)27-39(62)47(65)57-45(34-12-8-7-9-13-34)53(71)72-31(2)44(48(66)55-37)56-49(67)46-41(63)15-10-22-54-46/h7-10,12-13,15-19,22,31,33,35,37-40,43-45,63H,6,11,14,20-21,23-30H2,1-5H3,(H,55,66)(H,56,67)(H,57,65)/t31-,35+,37-,38+,39+,40+,43-,44+,45+/m1/s1
comment: Quinupristin is a semi-synthetic derivative of streptogramin B. It inhibits the late stage of protein synthesis by binding to the bacterial 50S ribosomal subunit.
iupac name: N-[(3S,6S,12R,15S,16R,19S,22S,25R)-25-[[(3S)-1-azabicyclo[2.2.2]octan-3-yl]sulfanylmethyl]-3-[[4-(dimethylamino)phenyl]methyl]-12-ethyl-4,16-dimethyl-2,5,11,14,18,21,24-heptaoxo-19-phenyl-17-oxa-1,4,10,13,20-pentazatricyclo[20.4.0.06,10]hexacosan-15-yl]-3-hydroxypyridine-2-carboxamide
xref: CHEMBL1200649
synonym: RP-57669
synonym: RP57669
synonym: RP 57669
synonym: Synercid® (dalfopristin + quinupristin)
approved: t
ligand name: quinupristin
type: SyntheticOrganicLigand

dalfopristin
in ch i key: SUYRLXYYZQTJHF-VMBLUXKRSA-N
in ch i: InChI=1S/C34H50N4O9S/c1-7-37(8-2)16-17-48(44,45)28-13-15-38-31(28)34(43)47-32(22(3)4)24(6)11-12-29(41)35-14-9-10-23(5)18-25(39)19-26(40)20-30-36-27(21-46-30)33(38)42/h9-12,18,21-22,24-25,28,31-32,39H,7-8,13-17,19-20H2,1-6H3,(H,35,41)/b10-9+,12-11+,23-18+/t24-,25-,28-,31-,32-/m1/s1
comment: Dalfopristin is a semi-synthetic derivative of streptogramin A. It inhibits the early phase of protein synthesis in the bacterial ribosome by binding to the 70S subunit. It is administered intravenously.
iupac name: (6R,7S,10R,11R,12E,17E,19E,21S)-6-[2-(diethylamino)ethylsulfonyl]-21-hydroxy-11,19-dimethyl-10-propan-2-yl-9,26-dioxa-3,15,28-triazatricyclo[23.2.1.03,7]octacosa-1(27),12,17,19,25(28)-pentaene-2,8,14,23-tetrone
synonym: RP-54476
synonym: RP54476
synonym: RP 54476
synonym: Synercid® (dalfopristin + quinupristin)
approved: t
ligand name: dalfopristin
type: SyntheticOrganicLigand

mesuximide
canonical SMILES: CN1C(=O)CC(C1=O)(C)c1ccccc1
isomeric SMILES: CN1C(=O)CC(C1=O)(C)c1ccccc1
in ch i key: AJXPJJZHWIXJCJ-UHFFFAOYSA-N
in ch i: InChI=1S/C12H13NO2/c1-12(9-6-4-3-5-7-9)8-10(14)13(2)11(12)15/h3-7H,8H2,1-2H3
comment: Mesuximide is marketed as a racemic mixture of stereoisomers; (R)-mesuximide and (S)-mesuximide. We show the non-stereo structure to represent the mixture.
iupac name: 1,3-dimethyl-3-phenylpyrrolidine-2,5-dione
xref: CHEMBL697
synonym: Celontin®
synonym: mesuximide
synonym: Petinutin®
approved: t
ligand name: mesuximide
type: SyntheticOrganicLigand

bederocin
in ch i key: BGJMKHPWCFXMOW-UHFFFAOYSA-N
comment: Bederocin (REP8839) is an antibacterial. It blocks bacterial protein synthesis by inhibiting methionyl tRNA synthetase <Reference id=39144/>.
xref: CHEMBL1631216
synonym: REP8839
synonym: REP-8839
synonym: REP 8839
approved: f
ligand name: bederocin
type: SyntheticOrganicLigand

cethromycin
in ch i key: PENDGIOBPJLVBT-ONLVEXIXSA-N
in ch i: InChI=1S/C42H59N3O10/c1-11-32-42(8)36(44-40(50)55-42)25(4)33(46)23(2)21-41(7,51-18-14-15-28-20-29-16-12-13-17-30(29)43-22-28)37(26(5)34(47)27(6)38(49)53-32)54-39-35(48)31(45(9)10)19-24(3)52-39/h12-17,20,22-27,31-32,35-37,39,48H,11,18-19,21H2,1-10H3,(H,44,50)/b15-14+/t23-,24-,25+,26+,27-,31+,32-,35-,36-,37-,39+,41-,42-/m1/s1
comment: Cethromycin is an orally bioavailable ketolide antibacterial that is structurally related to <Ligand id=1456/>. It was developed by Abbott Laboratories for potential to treat respiratory infections, including community acquired pneumonia (CAP) and for the prevention of post-exposure inhalational anthrax <Reference id=39204/><Reference id=39205/>.
iupac name: (1S,2R,5R,7R,8R,9R,11R,13R,14R)-8-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-2-ethyl-1,5,7,9,11,13-hexamethyl-9-[(E)-3-quinolin-3-ylprop-2-enoxy]-3,17-dioxa-15-azabicyclo[12.3.0]heptadecane-4,6,12,16-tetrone
synonym: ABT-773
synonym: ABT773
synonym: Abbott-195773
synonym: A-195773
synonym: Restanza®
approved: f
ligand name: cethromycin
type: SyntheticOrganicLigand

cetefloxacin
in ch i key: LTDOHCZUKCZDEQ-BJOHPYRUSA-N
in ch i: InChI=1S/C20H16F3N3O3/c1-9-15(24)8-25(9)18-6-17-11(5-14(18)23)19(27)12(20(28)29)7-26(17)16-3-2-10(21)4-13(16)22/h2-7,9,15H,8,24H2,1H3,(H,28,29)/t9-,15+/m0/s1
comment: Cetefloxacin is a fluoroquinolone class antibacterial <Reference id=39201/><Reference id=39202/><Reference id=39203/>.
iupac name: 7-[(2S,3R)-3-amino-2-methylazetidin-1-yl]-1-(2,4-difluorophenyl)-6-fluoro-4-oxoquinoline-3-carboxylic acid
xref: CHEMBL132468
synonym: E-4868
synonym: E4868
synonym: compound 43f [PMID: 7990118]
approved: f
ligand name: cetefloxacin
type: SyntheticOrganicLigand

tazobactam
in ch i key: LPQZKKCYTLCDGQ-WEDXCCLWSA-N
in ch i: InChI=1S/C10H12N4O5S/c1-10(5-13-3-2-11-12-13)8(9(16)17)14-6(15)4-7(14)20(10,18)19/h2-3,7-8H,4-5H2,1H3,(H,16,17)/t7-,8+,10+/m1/s1
comment: Tazobactam (CXA-201) is a β-lactamase inhibitor with antibacterial activity <Reference id=39199/>. It is used alongside β-lactam-containing antibacterials to reduce their lactamase-induced degradation. Chemically tazobactam is a penicillin derivative, that binds as an irreversible inhibitor of β-lactamase.
iupac name: (2S,3S,5R)-3-methyl-4,4,7-trioxo-3-(triazol-1-ylmethyl)-4λ6-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
xref: CHEMBL404
synonym: CXA-201
synonym: CXA201
synonym: Zerbaxa® (ceftolozane + tazobactam)
synonym: YTR 830H
synonym: YTR 830
approved: f
ligand name: tazobactam
type: SyntheticOrganicLigand

ceftolozane
canonical SMILES: NCCNC(=O)Nc1c[n+](n(c1N)C)CC1=C(C(=O)[O-])N2[C@H](SC1)[C@@H](C2=O)NC(=O)/C(=N/OC(C(=O)O)(C)C)/c1nsc(n1)N
isomeric SMILES: NCCNC(=O)Nc1c[n+](n(c1N)C)CC1=C(C(=O)[O-])N2[C@H](SC1)[C@@H](C2=O)NC(=O)/C(=N/OC(C(=O)O)(C)C)/c1nsc(n1)N
in ch i key: JHFNIHVVXRKLEF-DCZLAGFPSA-N
comment: Ceftolozane is a semi-synthetic, broad-spectrum, fifth-generation cephalosporin antibacterial with activity against certain Gram-negative (e.g. Pseudomonas spp.) and Gram-positive bacteria <Reference id=39195/>.
iupac name: (6R,7R)-3-[[3-amino-4-(2-aminoethylcarbamoylamino)-2-methylpyrazol-1-ium-1-yl]methyl]-7-[[(2Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(2-carboxypropan-2-yloxyimino)acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
synonym: CXA-101
synonym: CXA101
synonym: FR-264205
synonym: FR264205
synonym: FR 264205
synonym: Zerbaxa® (ceftolozane + tazobactam)
approved: t
ligand name: ceftolozane
type: SyntheticOrganicLigand

ceftizoxime alapivoxil
in ch i key: VOPANQNVVCPHQR-IVVGYLHBSA-N
in ch i: InChI=1S/C22H28N6O8S2/c1-10(23)15(29)26-21-24-11(8-38-21)13(27-34-5)16(30)25-14-17(31)28-12(6-7-37-18(14)28)19(32)35-9-36-20(33)22(2,3)4/h6,8,10,14,18H,7,9,23H2,1-5H3,(H,25,30)(H,24,26,29)/b27-13-/t10-,14+,18+/m0/s1
comment: Ceftizoxime alapivoxil is a third-generation cephalosporin antibacterial ester prodrug <Reference id=39184/><Reference id=39185/>.
iupac name: 2,2-dimethylpropanoyloxymethyl (6R,7R)-7-[[(2Z)-2-[2-[[(2S)-2-aminopropanoyl]amino]-1,3-thiazol-4-yl]-2-methoxyiminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
xref: CHEMBL2106058
synonym: AS924
synonym: KY020
synonym: AS-924
synonym: KY-020
approved: f
ligand name: ceftizoxime alapivoxil
type: SyntheticOrganicLigand

ceftizoxime
canonical SMILES: CO/N=C(/c1csc(n1)N)/C(=O)N[C@H]1[C@H]2SCC=C(N2C1=O)C(=O)O
isomeric SMILES: CO/N=C(/c1csc(n1)N)/C(=O)N[C@H]1[C@H]2SCC=C(N2C1=O)C(=O)O
in ch i key: NNULBSISHYWZJU-LLKWHZGFSA-N
in ch i: InChI=1S/C13H13N5O5S2/c1-23-17-7(5-4-25-13(14)15-5)9(19)16-8-10(20)18-6(12(21)22)2-3-24-11(8)18/h2,4,8,11H,3H2,1H3,(H2,14,15)(H,16,19)(H,21,22)/b17-7-/t8-,11-/m1/s1
comment: Ceftizoxime is a semisynthetic, broad-spectrum, β-lactamase-resistant, parenterally administered third-generation cephalosporin antibacterial with Gram +ve and Gram -ve activity. Unlike other third-generation cephalosporins, ceftizoxime's C-3 side chain has been removed to prevent deactivation by hydrolytic enzymes.
iupac name: (6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
xref: CHEMBL528
synonym: Cefizox®
synonym: FK 749
synonym: FK-749
synonym: FK749
synonym: FR 13749
synonym: FR-13749
synonym: FR13749
synonym: Epocelin®
synonym: SK&F 88373-Z
synonym: compound 22 {PMID: 2342058]
approved: t
ligand name: ceftizoxime
type: SyntheticOrganicLigand

nepafenac
canonical SMILES: NC(=O)Cc1cccc(c1N)C(=O)c1ccccc1
isomeric SMILES: NC(=O)Cc1cccc(c1N)C(=O)c1ccccc1
in ch i key: QEFAQIPZVLVERP-UHFFFAOYSA-N
in ch i: InChI=1S/C15H14N2O2/c16-13(18)9-11-7-4-8-12(14(11)17)15(19)10-5-2-1-3-6-10/h1-8H,9,17H2,(H2,16,18)
comment: Nepafenac is a non-steroidal anti-inflammatory drug (NSAID).
iupac name: 2-[2-amino-3-(benzoyl)phenyl]acetamide
xref: CHEMBL1021
synonym: AL-6515
synonym: AHR-9434
synonym: Nevanac®
approved: t
ligand name: nepafenac
type: SyntheticOrganicLigand

ceftiolene
in ch i key: WJXAHFZIHLTPFR-JLRJEBFFSA-N
in ch i: InChI=1S/C20H18N8O8S3/c1-36-26-10(9-7-39-19(21)22-9)13(30)23-11-15(32)28-12(18(34)35)8(6-38-17(11)28)2-5-37-20-25-24-14(31)16(33)27(20)3-4-29/h2,4-5,7,11,17H,3,6H2,1H3,(H2,21,22)(H,23,30)(H,24,31)(H,34,35)/b5-2+,26-10-/t11-,17-/m1/s1
comment: Ceftiolene is a semisynthetic, broad-spectrum, third-generation cephalosporin antibacterial <Reference id=39183/>.
iupac name: (6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-[(E)-2-[[5,6-dioxo-4-(2-oxoethyl)-1H-1,2,4-triazin-3-yl]sulfanyl]ethenyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
xref: CHEMBL2106102
synonym: cefatiolene
synonym: RP 42980
synonym: RP-42980
synonym: RP42980
synonym: RP 42,980
synonym: 42980RP
approved: f
ligand name: ceftiolene
type: SyntheticOrganicLigand

cefsulodin
in ch i key: SYLKGLMBLAAGSC-QLVMHMETSA-N
in ch i: InChI=1S/C22H20N4O8S2/c23-18(27)13-6-8-25(9-7-13)10-14-11-35-21-15(20(29)26(21)16(14)22(30)31)24-19(28)17(36(32,33)34)12-4-2-1-3-5-12/h1-9,15,17,21H,10-11H2,(H4-,23,24,27,28,30,31,32,33,34)/t15-,17-,21-/m1/s1
comment: Cefsulodin is a semi-synthetic, third-generation cephalosporin antibacterial. It is active against Pseudomonas aeruginosa and Staphylococcus aureus, but little activity against other bacteria <Reference id=39178/><Reference id=39179/>.
iupac name: (6R,7R)-3-[(4-carbamoylpyridin-1-ium-1-yl)methyl]-8-oxo-7-[[(2R)-2-phenyl-2-sulfoacetyl]amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
synonym: CGP7174/E
synonym: CGP-7174-E
synonym: Cefonomil®
approved: f
ligand name: cefsulodin
type: SyntheticOrganicLigand

ETX1317
in ch i key: CZCMDCKIUIXEQC-VQVTYTSYSA-N
in ch i: InChI=1S/C10H12FN3O5/c1-4-2-5(8(12)15)13-3-6(4)14(10(13)18)19-7(11)9(16)17/h2,5-7H,3H2,1H3,(H2,12,15)(H,16,17)/t5-,6+,7+/m1/s1
comment: ETX1317 is the active moiety of the prodrug <Ligand id=10781/>. It is a novel, broad spectrum, serine β-lactamase inhibitor of the diazabicyclooctane (DBO) class <Reference id=39177/>. ETX1317 restores and enhances activity of β-lactam antibacterials against multidrug resistant Enterobacteriales, including carbapenem-resistant strains.
iupac name: (2R)-2-{[(2R,5R)-2-carbamoyl-4-methyl-7-oxo-1,6-diazabicyclo[3.2.1]oct-3-en-6-yl]oxy}-2-fluoroacetic acid
synonym: ETX-1317
approved: f
ligand name: ETX1317
type: SyntheticOrganicLigand

ETX0282
in ch i key: OMNVFPBGXYKTDB-UTLUCORTSA-N
in ch i: InChI=1S/C13H18FN3O5/c1-6(2)21-12(19)10(14)22-17-9-5-16(13(17)20)8(11(15)18)4-7(9)3/h4,6,8-10H,5H2,1-3H3,(H2,15,18)/t8-,9+,10+/m1/s1
comment: ETX0282 is a broad spectrum inhibitor of Class A and C serine β-lactamases (including the carbapenemases KPC-2, OXA-24 and OXA-4) that is being developed by Entasis Therapeutics. It is the orally bioavailable prodrug of ETX1317 <Reference id=39177/>.
iupac name: isopropyl (R)-2-(((1R,2R,5R)-2-carbamoyl-4-methyl-7-oxo-1,6-diazabicyclo[3.2.1]oct-3-en-6-yl)oxy)-2-fluoroacetate
synonym: ETX-0282
approved: f
ligand name: ETX0282
type: SyntheticOrganicLigand

cefpimizole
in ch i key: LNZMRLHZGOBKAN-KAWPREARSA-N
comment: Cefpimizole (U 63196E) is a third-generation cephalosporin antibacterial with activity against Gram-positive and Gram-negative bacilli <Reference id=39173/><Reference id=39174/>.
iupac name: 2-[1-[[(6R,7R)-2-carboxy-7-[[(2R)-2-[(5-carboxy-1H-imidazole-4-carbonyl)amino]-2-phenylacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl]pyridin-1-ium-4-yl]ethanesulfonate
xref: CHEMBL2103902
synonym: U 63196E
synonym: U-63196E
synonym: CPIZ
synonym: U-63,196
approved: f
ligand name: cefpimizole
type: SyntheticOrganicLigand

sulfadoxine
canonical SMILES: COc1c(OC)ncnc1NS(=O)(=O)c1ccc(cc1)N
isomeric SMILES: COc1c(OC)ncnc1NS(=O)(=O)c1ccc(cc1)N
in ch i key: PJSFRIWCGOHTNF-UHFFFAOYSA-N
in ch i: InChI=1S/C12H14N4O4S/c1-19-10-11(14-7-15-12(10)20-2)16-21(17,18)9-5-3-8(13)4-6-9/h3-7H,13H2,1-2H3,(H,14,15,16)
comment: Sulfadoxine is a sulfonamide containing compound with antimalarial activity. It is used in the treatment of malaria as a combination therapy. The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
iupac name: 4-amino-N-(5,6-dimethoxypyrimidin-4-yl)benzenesulfonamide
xref: CHEMBL1539
synonym: sulphadoxine
approved: t
ligand name: sulfadoxine
type: SyntheticOrganicLigand

cefmatilen
in ch i key: UEQVTKSAEXANEZ-DKQCJYJNSA-N
in ch i: InChI=1S/C15H14N8O5S4/c16-15-18-5(2-30-15)8(21-28)11(24)19-9-12(25)23-10(14(26)27)6(3-29-13(9)23)31-4-32-7-1-17-22-20-7/h1-2,9,13,28H,3-4H2,(H2,16,18)(H,19,24)(H,26,27)(H,17,20,22)/b21-8+/t9-,13-/m1/s1
comment: Cefmatilen (S-1090) is an orally-active cephalosporin antibacterial hat was first reported in the mid 1990s <Reference id=39171/>. It is highly active against a variety of Gram-positive and Gram-negative bacteria, including Streptococcus pyogenes and Neisseria gonorrhoeae in vitro.
iupac name: (6R,7R)-7-[[(2E)-2-(2-amino-1,3-thiazol-4-yl)-2-hydroxyiminoacetyl]amino]-8-oxo-3-(2H-triazol-4-ylsulfanylmethylsulfanyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
synonym: S-1090
synonym: S1090
approved: f
ligand name: cefmatilen
type: SyntheticOrganicLigand

cefluprenam
in ch i key: XAKKNLNAJBNLPC-MAYKBZFQSA-N
comment: Cefluprenam (E-1077) is a parenteral cephalosporin antibacterial <Reference id=39169/><Reference id=39170/>. It exhibits broad in vitro antibacterial activity against gram-positive and gram-negative bacteria.
iupac name: (6R,7R)-3-[(E)-3-[(2-amino-2-oxoethyl)-ethyl-methylazaniumyl]prop-1-enyl]-7-[[(2Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(fluoromethoxyimino)acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
xref: CHEMBL2074822
synonym: E-1077
synonym: E1077
approved: f
ligand name: cefluprenam
type: SyntheticOrganicLigand

cefiderocol
in ch i key: DBPPRLRVDVJOCL-FQRUVTKNSA-N
comment: Cefiderocol (S-649266) is a novel parenteral cephalosporin antibacterial with Gram-negative activity including against multi-drug resistant bacteria <Reference id=39166/><Reference id=39167/>. Chemically it is a catechol-conjugated siderophore cephalosporin. It was developed to treat bloodstream infections, hospital-acquired and ventilator-associated bacterial pneumonia, and complicated urinary tract infections. It can be formulated as the sulphate tosylate complex. Cefiderocol was the first siderophore class antibacterial to be approved by FDA.
iupac name: (6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(2-carboxypropan-2-yloxyimino)acetyl]amino]-3-[[1-[2-[(2-chloro-3,4-dihydroxybenzoyl)amino]ethyl]pyrrolidin-1-ium-1-yl]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
xref: CHEMBL3989974
synonym: S-649266
synonym: GSK-2696266
synonym: RSC 649266
synonym: RSC-649266
synonym: RSC649266
synonym: GSK2696266
synonym: compound 3 [PMID: 29960205]
synonym: Fetroja®
synonym: Fetcroja®
approved: t
ligand name: cefiderocol
type: SyntheticOrganicLigand

cefetecol
canonical SMILES: OC(=O)[C@H](c1ccc(c(c1)O)O)O/N=C(/c1csc(n1)N)/C(=O)N[C@@H]1C(=O)N2[C@@H]1SCC=C2C(=O)O
isomeric SMILES: OC(=O)[C@H](c1ccc(c(c1)O)O)O/N=C(/c1csc(n1)N)/C(=O)N[C@@H]1C(=O)N2[C@@H]1SCC=C2C(=O)O
in ch i key: ILZCDOYRDFDUPN-UITOYEBDSA-N
in ch i: InChI=1S/C20H17N5O9S2/c21-20-22-8(6-36-20)12(24-34-14(19(32)33)7-1-2-10(26)11(27)5-7)15(28)23-13-16(29)25-9(18(30)31)3-4-35-17(13)25/h1-3,5-6,13-14,17,26-27H,4H2,(H2,21,22)(H,23,28)(H,30,31)(H,32,33)/b24-12+/t13-,14+,17-/m1/s1
comment: Cefetecol (GR69153) is a broad-spectrum, fourth-generation (catechol-substituted) parenteral cephalosporin antibacterial <Reference id=39164/><Reference id=39165/>. It was designed to be active against Gram +ve and -ve bacilli that cause enteric infections, but development was terminated.
iupac name: (6R,7R)-7-[[(2E)-2-(2-amino-1,3-thiazol-4-yl)-2-[(S)-carboxy-(3,4-dihydroxyphenyl)methoxy]iminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
xref: CHEMBL2304034
synonym: GR69153
synonym: GR-69153
synonym: GR-69153X
approved: f
ligand name: cefetecol
type: SyntheticOrganicLigand

taniborbactam
in ch i key: PFZUWUXKQPRWAL-PXCJXSSVSA-N
in ch i: InChI=1S/C19H28BN3O5/c21-8-9-22-14-6-4-12(5-7-14)10-17(24)23-16-11-13-2-1-3-15(19(25)26)18(13)28-20(16)27/h1-3,12,14,16,22,27H,4-11,21H2,(H,23,24)(H,25,26)/t12?,14?,16-/m0/s1
comment: Taniborbactam (VNRX-5133) is a clinical stage, injectable, broad-spectrum β-lactamase inhibitor. It has activity against both serine- and metallo-β-lactamases (e.g. oxacillinase, Klebsiella pneumoniae carbapenemase, New Delhi metallo-beta-lactamase, Verona integron-encoded metallo-beta-lactamase and extended spectrum beta-lactamase) <Reference id=39163/>. Taniborbactam is being developed by Venatorx Pharmaceuticals.
iupac name: (3R)-3-[[2-[4-(2-aminoethylamino)cyclohexyl]acetyl]amino]-2-hydroxy-3,4-dihydro-1,2-benzoxaborinine-8-carboxylic acid
synonym: VNRX-5133
synonym: VNRX5133
approved: f
ligand name: taniborbactam
type: SyntheticOrganicLigand

cenobamate
canonical SMILES: NC(=O)O[C@H](c1ccccc1Cl)Cn1nncn1
isomeric SMILES: NC(=O)O[C@H](c1ccccc1Cl)Cn1nncn1
in ch i key: GFHAXPJGXSQLPT-VIFPVBQESA-N
in ch i: InChI=1S/C10H10ClN5O2/c11-8-4-2-1-3-7(8)9(18-10(12)17)5-16-14-6-13-15-16/h1-4,6,9H,5H2,(H2,12,17)/t9-/m0/s1
comment: Cenobamate (YKP-3089) is an oral anti-epilepsy drug. Pharmacological evidence shows that it acts as a positive allosteric modulator (PAM) at GABAA channels <Reference id=39159/> and as an inhibitor of the INaP current via voltage-gated sodium channels <Reference id=39160/> in isolated rat hippocampal neurons.
iupac name: [(1R)-1-(2-chlorophenyl)-2-(tetrazol-2-yl)ethyl] carbamate
xref: CHEMBL3989949
synonym: YKP3089
synonym: YKP-3089
synonym: Xcopri®
synonym: Ontozry®
approved: t
ligand name: cenobamate
type: SyntheticOrganicLigand

cefclidin
in ch i key: JUVHVMCKLDZLGN-TVNFHGJBSA-N
in ch i: InChI=1S/C21H26N8O6S2/c1-35-26-11(14-25-20(23)37-27-14)15(30)24-12-16(31)28-13(18(32)33)10(9-36-17(12)28)8-29-5-2-21(3-6-29,4-7-29)19(22)34/h12,17H,2-9H2,1H3,(H5-,22,23,24,25,27,30,32,33,34)/b26-11-/t12-,17-,21?,29?/m1/s1
comment: Cefclidin (E1040) is a fourth-generation cephalosporin antibacterial that disrupts cell wall formation <Reference id=39154/><Reference id=39155/>. It exhibits strong antibacterial activity against glucose non-fermentative bacillus bacteria, but is ineffective against gram-positive cocci.
iupac name: (6R,7R)-7-[[(2Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-methoxyiminoacetyl]amino]-3-[(4-carbamoyl-1-azoniabicyclo[2.2.2]octan-1-yl)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
xref: CHEMBL1614665
synonym: cefclidine
synonym: E1040
synonym: E-1040
approved: f
ligand name: cefclidin
type: SyntheticOrganicLigand

cefazaflur
in ch i key: HGXLJRWXCXSEJO-GMSGAONNSA-N
comment: Cefazaflur (SK&F 59962) is a semisynthetic first generation cephalosporin antibacterial <Reference id=39152/>. It did not progress beyond preclinical development. Cefazaflur binds to and inactivates penicillin-binding proteins (PBPs) and thereby disrupts normal bacterial cell wall assembly.
iupac name: (6R,7R)-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-7-[[2-(trifluoromethylsulfanyl)acetyl]amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
xref: CHEMBL2110623
synonym: SK&F 59962
approved: f
ligand name: cefazaflur
type: SyntheticOrganicLigand

sulbactam
in ch i key: FKENQMMABCRJMK-RITPCOANSA-N
in ch i: InChI=1S/C8H11NO5S/c1-8(2)6(7(11)12)9-4(10)3-5(9)15(8,13)14/h5-6H,3H2,1-2H3,(H,11,12)/t5-,6+/m1/s1
comment: Sulbactam is a β-lactamase inhibitor that is used to limit degradation of β-lactam antibacterials. Its synergy with β-lactam antibacterials against some multiply drug-resistant Enterobacteriaceae and Pseudomonas species is reported to be inconsistent, likely as it cannot inhibit the AmpC cephalosporinase expressed by these species <Reference id=39151/>.
iupac name: (2S,5R)-3,3-dimethyl-4,4,7-trioxo-4λ6-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
xref: CHEMBL403
synonym: CP-45,899
synonym: CP-45899
synonym: Betamaze
approved: t
ligand name: sulbactam
type: SyntheticOrganicLigand

cadazolid
in ch i key: XWFCFMXQTBGXQW-GOSISDBHSA-N
in ch i: InChI=1S/C29H29F2N3O8/c30-21-10-19-23(33(16-1-2-16)13-20(26(19)36)27(37)38)11-24(21)32-7-5-29(40,6-8-32)15-41-25-4-3-17(9-22(25)31)34-12-18(14-35)42-28(34)39/h3-4,9-11,13,16,18,35,40H,1-2,5-8,12,14-15H2,(H,37,38)/t18-/m1/s1
comment: Cadazolid (ACT-179811) is a quinolonyl-oxazolidinone (quinoxolidinone) antibacterial with Gram-positive activity. It targets the bacterial protein synthesis machinery by binding to the peptidyl transferase centre (PTC) of the ribosome <Reference id=39149/>.
iupac name: 1-cyclopropyl-6-fluoro-7-[4-[[2-fluoro-4-[(5R)-5-(hydroxymethyl)-2-oxo-1,3-oxazolidin-3-yl]phenoxy]methyl]-4-hydroxypiperidin-1-yl]-4-oxoquinoline-3-carboxylic acid
xref: CHEMBL3707376
synonym: ACT-179811
synonym: ACT179811
approved: f
ligand name: cadazolid
type: SyntheticOrganicLigand

butikacin
in ch i key: OCFOTEIMZBKQFS-DGMGPCKZSA-N
in ch i: InChI=1S/C22H45N5O12/c23-2-1-7(29)5-27-9-3-8(25)19(38-22-17(34)16(33)14(31)10(4-24)36-22)18(35)20(9)39-21-15(32)12(26)13(30)11(6-28)37-21/h7-22,27-35H,1-6,23-26H2/t7-,8-,9+,10+,11+,12-,13+,14+,15+,16-,17+,18-,19+,20-,21+,22+/m0/s1
comment: Butikacin (UK-18892) is a semisynthetic aminoglycoside class antibacterial <Reference id=39147/>. It has activity against Gram-positive bacilli.
iupac name: (2R,3R,4S,5S,6R)-2-[(1R,2S,3S,4R,6S)-6-amino-3-[(2S,3R,4S,5S,6R)-4-amino-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4-[[(2S)-4-amino-2-hydroxybutyl]amino]-2-hydroxycyclohexyl]oxy-6-(aminomethyl)oxane-3,4,5-triol
xref: CHEMBL2304044
synonym: UK18892
synonym: UK-18892
synonym: UK-18,892
approved: f
ligand name: butikacin
type: SyntheticOrganicLigand

bluensomycin
in ch i key: RQLDKUSQKQMFCN-AEXVNIBOSA-N
in ch i: InChI=1S/C21H39N5O14/c1-5-21(35,4-28)16(40-17-8(25-2)10(30)9(29)6(3-27)37-17)18(36-5)38-14-7(26-19(22)23)11(31)15(39-20(24)34)13(33)12(14)32/h5-18,25,27-33,35H,3-4H2,1-2H3,(H2,24,34)(H4,22,23,26)/t5-,6-,7-,8-,9-,10-,11-,12+,13+,14+,15+,16-,17-,18-,21+/m0/s1
comment: Bluensomycin (U-12898) is an antibacterial with Gram-negative activity <Reference id=39145/>.
iupac name: [(1R,2S,3S,4R,5R,6R)-3-(diaminomethylideneamino)-4-[(2R,3R,4R,5S)-3-[(2S,3S,4S,5R,6S)-4,5-dihydroxy-6-(hydroxymethyl)-3-(methylamino)oxan-2-yl]oxy-4-hydroxy-4-(hydroxymethyl)-5-methyloxolan-2-yl]oxy-2,5,6-trihydroxycyclohexyl] carbamate
xref: CHEMBL2104642
synonym: U-12898
synonym: U12898
synonym: bluensin
approved: f
ligand name: bluensomycin
type: SyntheticOrganicLigand

cefepime
in ch i key: HVFLCNVBZFFHBT-ZKDACBOMSA-N
in ch i: InChI=1S/C19H24N6O5S2/c1-25(5-3-4-6-25)7-10-8-31-17-13(16(27)24(17)14(10)18(28)29)22-15(26)12(23-30-2)11-9-32-19(20)21-11/h9,13,17H,3-8H2,1-2H3,(H3-,20,21,22,26,28,29)/b23-12-/t13-,17-/m1/s1
comment: Cefepime is a semisynthetic, broad-spectrum, fourth-generation cephalosporin antibacterial <Reference id=39157/><Reference id=39158/>. It was removed from the World Health Organization's List of Essential Medicines in 2019.
iupac name: (6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-[(1-methylpyrrolidin-1-ium-1-yl)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
xref: CHEMBL186
synonym: CFPM
synonym: BMY-28142
synonym: BMY28142
synonym: Maxipime®
synonym: Renapime®
approved: t
ligand name: cefepime
type: SyntheticOrganicLigand

carbenicillin
in ch i key: FPPNZSSZRUTDAP-UWFZAAFLSA-N
in ch i: InChI=1S/C17H18N2O6S/c1-17(2)11(16(24)25)19-13(21)10(14(19)26-17)18-12(20)9(15(22)23)8-6-4-3-5-7-8/h3-7,9-11,14H,1-2H3,(H,18,20)(H,22,23)(H,24,25)/t9?,10-,11+,14-/m1/s1
comment: Carbenicillin is a broad-spectrum, semi-synthetic carboxypenicillin antibacterial. It has Gram-negative activity, including against Pseudomonas aeruginosa, but has limited Gram-positive coverage. It is sensitive to β-lactamase degradation.
iupac name: (2S,5R,6R)-6-[(2-carboxy-2-phenylacetyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
xref: CHEMBL1214
synonym: carboxybenzylpenicillin
synonym: CBPC
synonym: BRL-2064
synonym: BRL2064
synonym: CP 15639-2
synonym: CP-156392
synonym: Pyopen®
approved: t
ligand name: carbenicillin
type: SyntheticOrganicLigand

apramycin
in ch i key: XZNUGFQTQHRASN-XQENGBIVSA-N
in ch i: InChI=1S/C21H41N5O11/c1-26-11-14(30)18-8(33-20(11)37-21-16(32)13(29)10(25)9(4-27)34-21)3-7(24)19(36-18)35-17-6(23)2-5(22)12(28)15(17)31/h5-21,26-32H,2-4,22-25H2,1H3/t5-,6+,7-,8+,9-,10-,11+,12+,13+,14-,15-,16-,17-,18+,19+,20-,21-/m1/s1
comment: Apramycin is a deoxystreptamine class antibacterial with Gram-negative activity <Reference id=39139/><Reference id=39140/>.
iupac name: (2R,3R,4S,5S,6S)-2-[[(2R,3S,4R,4aR,6S,7R,8aS)-7-amino-6-[(1R,2R,3S,4R,6S)-4,6-diamino-2,3-dihydroxycyclohexyl]oxy-4-hydroxy-3-(methylamino)-2,3,4,4a,6,7,8,8a-octahydropyrano[3,2-b]pyran-2-yl]oxy]-5-amino-6-(hydroxymethyl)oxane-3,4-diol
xref: CHEMBL1230961
synonym: Nebramycin II
synonym: Nebramycin factor 2
synonym: EL857
synonym: EL-857
approved: f
ligand name: apramycin
type: SyntheticOrganicLigand

apalcillin
in ch i key: XMQVYNAURODYCQ-SLFBBCNNSA-N
in ch i: InChI=1S/C25H23N5O6S/c1-25(2)19(24(35)36)30-22(34)17(23(30)37-25)29-21(33)15(12-7-4-3-5-8-12)28-20(32)13-11-27-14-9-6-10-26-16(14)18(13)31/h3-11,15,17,19,23H,1-2H3,(H,27,31)(H,28,32)(H,29,33)(H,35,36)/t15-,17-,19+,23-/m1/s1
comment: Apalcillin (PC-904) is a semisynthetic penicillin (β-lactam) derivative antibacterial <Reference id=39138/><Reference id=39137/>. It is highly active against Pseudomonas species. Toxicity issues meant that this compound did not progress beyond preclinical evaluation.
iupac name: (2S,5R,6R)-3,3-dimethyl-7-oxo-6-[[(2R)-2-[(4-oxo-1H-1,5-naphthyridine-3-carbonyl)amino]-2-phenylacetyl]amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
xref: CHEMBL3306902
synonym: PC-904
synonym: PC904
synonym: WY-44,417
synonym: WY-44417
approved: f
ligand name: apalcillin
type: SyntheticOrganicLigand

amifloxacin
in ch i key: RUXPNBWPIRDVTH-UHFFFAOYSA-N
in ch i: InChI=1S/C16H19FN4O3/c1-18-21-9-11(16(23)24)15(22)10-7-12(17)14(8-13(10)21)20-5-3-19(2)4-6-20/h7-9,18H,3-6H2,1-2H3,(H,23,24)
comment: Amifloxacin (WIN 49375) is a fluoroquinolone type II DNA topoisomerase (DNA gyrase) inhibitor antibacterial <Reference id=39135/><Reference id=39136/>.
iupac name: 6-fluoro-1-(methylamino)-7-(4-methylpiperazin-1-yl)-4-oxoquinoline-3-carboxylic acid
xref: CHEMBL6231
synonym: WIN 49, 375
synonym: WIN-49375
synonym: WIN49375
synonym: WIN 49,375-3
synonym: compound 7 [PMID: 2834557]
approved: f
ligand name: amifloxacin
type: SyntheticOrganicLigand

SC-560
in ch i key: PQUGCKBLVKJMNT-UHFFFAOYSA-N
comment: SC-560 is a selective COX-1 inhibitor <Reference id=37048/>.
iupac name: 5-(4-chlorophenyl)-1-(4-methoxyphenyl)-3-(trifluoromethyl)pyrazole
xref: CHEMBL26915
synonym: SC560
approved: f
ligand name: SC-560
type: SyntheticOrganicLigand

levonadifloxacin
in ch i key: JYJTVFIEFKZWCJ-JTQLQIEISA-N
in ch i: InChI=1S/C19H21FN2O4/c1-10-2-3-12-16-13(18(24)14(19(25)26)9-22(10)16)8-15(20)17(12)21-6-4-11(23)5-7-21/h8-11,23H,2-7H2,1H3,(H,25,26)/t10-/m0/s1
comment: Levonadifloxacin (WCK 771) is a fluoroquinolone class antibacterial <Reference id=39132/><Reference id=39134/><Reference id=39133/>. It is being developed as a component of a combination therapy with <Ligand id=10756/>. Formulated as the levonadifloxacin arginine salt for clinical administration. We show the structure of the parent molecule here.
xref: CHEMBL190561
synonym: WCK 771
synonym: WCK771
synonym: WCK-771
synonym: (S)-(-)-nadifloxacin
approved: f
ligand name: levonadifloxacin
type: SyntheticOrganicLigand

alalevonadifloxacin
in ch i key: OUXXDXXQNWKOIF-RYUDHWBXSA-N
in ch i: InChI=1S/C22H26FN3O5/c1-11-3-4-14-18-15(20(27)16(21(28)29)10-26(11)18)9-17(23)19(14)25-7-5-13(6-8-25)31-22(30)12(2)24/h9-13H,3-8,24H2,1-2H3,(H,28,29)/t11-,12-/m0/s1
comment: Alalevonadifloxacin is a benzoquinolizine fluoroquinolone class antibacterial. It is being developed as a component of a combination therapy with <Ligand id=10757/>.
synonym: WCK-2349
synonym: WCK 2349
synonym: WCK2349
approved: f
ligand name: alalevonadifloxacin
type: SyntheticOrganicLigand

DEBIO 1452
canonical SMILES: O=C1CCc2c(N1)ncc(c2)/C=C/C(=O)N(Cc1oc2c(c1C)cccc2)C
isomeric SMILES: O=C1CCc2c(N1)ncc(c2)/C=C/C(=O)N(Cc1oc2c(c1C)cccc2)C
in ch i key: QXTWSUQCXCWEHF-JXMROGBWSA-N
in ch i: InChI=1S/C22H21N3O3/c1-14-17-5-3-4-6-18(17)28-19(14)13-25(2)21(27)10-7-15-11-16-8-9-20(26)24-22(16)23-12-15/h3-7,10-12H,8-9,13H2,1-2H3,(H,23,24,26)/b10-7+
comment: DEBIO 1452 (previously AFN-1252) is the active metabolite of afabicin (DEBIO 1450) <Reference id=39130/>. It is an inhibitor of bacterial Fabl, the NADH-dependent enoyl reductase from the type II bacterial fatty acid biosynthesis pathway (FAS-II) <Reference id=39127/><Reference id=39128/>. It specifically targets staphylococci without significant activity against other Gram +ve or Gram -ve species <Reference id=39127/>.
iupac name: (E)-N-methyl-N-[(3-methyl-1-benzofuran-2-yl)methyl]-3-(7-oxo-6,8-dihydro-5H-1,8-naphthyridin-3-yl)prop-2-enamide
xref: CHEMBL1652621
synonym: DEBIO-1452
synonym: DEBIO1452
synonym: AFN-1252
synonym: AFN-12520000
synonym: afabicin desphosphono
approved: f
ligand name: DEBIO 1452
type: SyntheticOrganicLigand

acorafloxacin
in ch i key: VMKVDAAFMQKZJS-LFIBNONCSA-N
in ch i: InChI=1S/C21H23F2N3O4/c1-30-20-17-13(19(27)14(21(28)29)10-26(17)12-4-5-12)7-15(22)18(20)25-6-2-3-11(9-25)16(23)8-24/h7,10,12H,2-6,8-9,24H2,1H3,(H,28,29)/b16-11+
comment: Acorafloxacin is a fluoroquinolone class antibacterial <Reference id=39126/>.
iupac name: 7-[(3E)-3-(2-amino-1-fluoroethylidene)piperidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxy-4-oxoquinoline-3-carboxylic acid
xref: CHEMBL1257096
synonym: avarofloxacin (former name)
synonym: JNJ-Q2
synonym: JNJQ2
approved: f
ligand name: acorafloxacin
type: SyntheticOrganicLigand

(R)-16 [PMID: 32267688]
in ch i key: GTNKAJJMCCFDIU-QGZVFWFLSA-N
comment: (R)-16 is a modulator of the nuclear peroxisome proliferator-activated receptor γ (PPARγ) <Reference id=39109/>. Its chemical structure is a novel chemotype for this receptor, and it binds in the orthosteric PPARγ ligand-binding site in a pose that is distinct from existing modulators.
iupac name: (2R)-2-[[6-[(2,4-dichlorophenyl)sulfonylamino]-1,3-benzothiazol-2-yl]sulfanyl]octanoic acid
approved: f
ligand name: (R)-16 [PMID: 32267688]
type: SyntheticOrganicLigand

MLN-3897
in ch i key: ZGFJFBOLVLFLLN-ZNLRHDTNSA-N
in ch i: InChI=1S/C32H37ClN2O3/c1-30(2)21-35(18-15-32(30,37)22-9-12-24(33)13-10-22)17-6-8-25-26-7-5-16-34-28(26)20-38-29-14-11-23(19-27(25)29)31(3,4)36/h5,7-14,16,19,36-37H,6,15,17-18,20-21H2,1-4H3/b25-8+
comment: MLN-3897 is a selective oral, small‐molecule receptor antagonist of CCR1 <Reference id=39107/> and clinical lead that was developed for immunomodulatory potential and as a chemokine signalling inhibitor to reduce multiple myeloma (MM)-related osteolytic bone disease (blocking CCL3-CCR1-mediated signalling inhibits osteoclast formation and MM cell migration and survival) <Reference id=39105/>. We show the chemical structure here without specified stereochemistry, as depicted in the 2016 article by Pusalkar et al. <Reference id=39107/>. A stereo-specified enantiomer is claimed as (abs)-50 in MIllenium Pharmaceuticals' patent US20090286823 <Reference id=39108/>. As there has been no formal disclosure of the name-to-structure, we show the 'flat' structure in good faith. Analysis presented in a bioRxiv preprint (not peer reviewed) suggests that MLN-3897 impairs infection by SARS-CoV-2 in vitro <Reference id=39099/>.
synonym: MLN3897
synonym: AVE-9897
synonym: AVE9897
approved: f
ligand name: MLN-3897
type: SyntheticOrganicLigand

example 4 [WO2017114509]
in ch i key: BRFDPJYHCJVJEP-ZJOUEHCJSA-N
in ch i: InChI=1S/C25H26N4O4/c30-15-19(13-18-10-11-26-23(18)31)27-24(32)21(12-16-6-2-1-3-7-16)29-25(33)22-14-17-8-4-5-9-20(17)28-22/h1-9,14-15,18-19,21,28H,10-13H2,(H,26,31)(H,27,32)(H,29,33)/t18-,19-,21-/m0/s1
comment: Example 4 is an inhibitor of SARS-CoV main protease (Mpro, 3CLpro) from patent (in Chinese) WO2017114509. It is the most potent from the set that was derived from structure-activity relationship-based design. In April 2021, this copmound was reported as an inhibitor of 3C proteases from enteroviruses and rhinoviruses and of the SARS-CoV-2 Mpro <Reference id=41991/>.
iupac name: N-[(2S)-1-oxo-1-[[(2S)-1-oxo-3-[(3S)-2-oxopyrrolidin-3-yl]propan-2-yl]amino]-3-phenylpropan-2-yl]-1H-indole-2-carboxamide
synonym: compound 18p [PMID: 33872498]
approved: f
ligand name: example 4 [WO2017114509]
type: SyntheticOrganicLigand

compound 3k [PMID: 24568342]
in ch i key: XJTWGMHOQKGBDO-GOSISDBHSA-N
in ch i: InChI=1S/C25H27FN2O/c1-18(23-11-5-8-20-7-2-3-10-24(20)23)28-14-12-21(13-15-28)25(29)27-17-19-6-4-9-22(26)16-19/h2-11,16,18,21H,12-15,17H2,1H3,(H,27,29)/t18-/m1/s1
comment: Compound 3k is reported as an inhibitor of the papain-like protease (PL-pro) of SARS-CoV <Reference id=39102/>. It was the most potent in the series both in terms of inhibiting enzyme activity (IC50 150 nM) and in terms of reducung viral replication in cell culture (EC50 = 5400 nM). The X-ray structure of the PL-pro/3k complex was submitted to the RCSB Protein Data Bank and has accession 4OW0. Activity of 3k vs. SARS-CoV-2 PL-pro has not yet been published.
iupac name: N-[(3-fluorophenyl)methyl]-1-[(1R)-1-naphthalen-1-ylethyl]piperidine-4-carboxamide
xref: CHEMBL3233815
approved: f
ligand name: compound 3k [PMID: 24568342]
type: SyntheticOrganicLigand

ONO-5334
canonical SMILES: O=C(C1CCCCCC1)N[C@H](C(=O)C(=O)N/N=C/1/SC[C@H](N1C)C)C1CCOCC1
isomeric SMILES: O=C(C1CCCCCC1)N[C@H](C(=O)C(=O)N/N=C/1/SC[C@H](N1C)C)C1CCOCC1
in ch i key: BTZCSXIUAFVRTE-CHGLIHOBSA-N
in ch i: InChI=1S/C21H34N4O4S/c1-14-13-30-21(25(14)2)24-23-20(28)18(26)17(15-9-11-29-12-10-15)22-19(27)16-7-5-3-4-6-8-16/h14-17H,3-13H2,1-2H3,(H,22,27)(H,23,28)/b24-21-/t14-,17+/m1/s1
comment: ONO-5334 is a cysteine protease inhibitor with activity against cathepsin K. It was an oral drug lead that was considered as a bone resorption inhibitor for the treatment of postmenopausal osteoporosis. ONO-5334 has some antiviral activity against SARS-CoV-2, and antagonises viral replication in human iPSC-derived pneumocyte-like cells <Reference id=39099/>.
iupac name: N-[(1S)-3-[(2Z)-2-[(4R)-3,4-dimethyl-1,3-thiazolidin-2-ylidene]hydrazinyl]-1-(oxan-4-yl)-2,3-dioxopropyl]cycloheptanecarboxamide
synonym: ONO 5334
synonym: ONO5334
approved: f
ligand name: ONO-5334
type: SyntheticOrganicLigand

compound 2-2c [PMID: 32003560]
canonical SMILES: COc1ccc2c(c1)n(CCCC(=O)N)c1c2ccnc1C
isomeric SMILES: COc1ccc2c(c1)n(CCCC(=O)N)c1c2ccnc1C
in ch i key: MRZRJTZGNFPMNY-UHFFFAOYSA-N
in ch i: InChI=1S/C17H19N3O2/c1-11-17-14(7-8-19-11)13-6-5-12(22-2)10-15(13)20(17)9-3-4-16(18)21/h5-8,10H,3-4,9H2,1-2H3,(H2,18,21)
comment: Compound 2-2c is a selective inhibitor of DYRK1A whose chemical structure is derived from that of the DYRK1 kinase inhibitor <Ligand id=9352/> <Reference id=38848/>. It was developed for potential to promote pancreatic β-cell proliferation as a novel mechanism to be applied to the treatment of type 1 diabetes. It produces predicted effects on β-cells in vitro and in vivo. See also <Ligand id=10687/>, which is a selective DYRK1A inhibitor with a different chemical scaffold <Reference id=38842/>.
iupac name: 4-(7-methoxy-1-methylpyrido[3,4-b]indol-9-yl)butanamide
approved: f
ligand name: compound 2-2c [PMID: 32003560]
type: SyntheticOrganicLigand

VBY-825
in ch i key: PPUXXDKQNAHHON-BJLQDIEVSA-N
comment: VBY-825 is a reversible cysteine protease inhibitor with high potency against cathepsins B, L, S and V <Reference id=39100/>. Human cysteinyl cathepsins are required for proteolytic processing of virally encoded proteins during infection <Reference id=40002/><Reference id=40001/><Reference id=40003/>, including a likely requirement for proper processing of the SARS-CoV-2 S protein within the endosome (activating its fusogenic acitivity) <Reference id=40001/>. Experimental evidence indicates that VBY-825 has some antiviral activity against SARS-CoV-2 <Reference id=39099/>. In in vitro experiments VBY-825 inhibits SARS-CoV-2 entry. It does not inhibit the viral 3C-like protease (3CLpro) or papain-like protease (PLpro), which suggests that its antiviral activity is associated with inhibition of host proteases. In the oncology setting, a pre-clinical model of pancreatic islet cancer revealed that VBY-825 exhibits significant anti-tumour activity.
synonym: VBY825
approved: f
ligand name: VBY-825
type: SyntheticOrganicLigand

MDL-28170
in ch i key: NGBKFLTYGSREKK-PMACEKPBSA-N
in ch i: InChI=1S/C22H26N2O4/c1-16(2)20(24-22(27)28-15-18-11-7-4-8-12-18)21(26)23-19(14-25)13-17-9-5-3-6-10-17/h3-12,14,16,19-20H,13,15H2,1-2H3,(H,23,26)(H,24,27)/t19-,20-/m0/s1
comment: MDL-28170 is a calpain and cathepsin B inhibitor <Reference id=39098/>. It impairs impairs infection by SARS-CoV and Ebola virus (EBOV). MDL-28170 has some antiviral activity against SARS-CoV-2, and antagonises viral replication in human iPSC-derived pneumocyte-like cells <Reference id=39099/>.
iupac name: benzyl N-[(2S)-3-methyl-1-oxo-1-[[(2S)-1-oxo-3-phenylpropan-2-yl]amino]butan-2-yl]carbamate
synonym: N-benzyloxycarbonyl-L-valyl-L-phenylalaninal
synonym: MDL28170
synonym: N-CBZ-Val-Phe-al
synonym: calpain inhibitor III
approved: f
ligand name: MDL-28170
type: SyntheticOrganicLigand

golidocitinib
in ch i key: CVCVOSPZEVINRM-MRXNPFEDSA-N
in ch i: InChI=1S/C25H31N9O2/c1-16(34-12-10-32(2)11-13-34)23(35)28-20-7-5-6-17-18(14-27-22(17)20)19-8-9-26-25(29-19)30-21-15-33(3)31-24(21)36-4/h5-9,14-16,27H,10-13H2,1-4H3,(H,28,35)(H,26,29,30)/t16-/m1/s1
comment: AZD4205 is a selective, orally bioavailable, ATP-competitive inhibitor of Janus kinase 1 (JAK1) that was developed by Dizal Pharmaceutical Company <Reference id=39092/>. It has been shown to enhance antitumour activity in combination with <Ligand id=7719/> (an approved EGFR inhibitor) in a preclinical non-small cell lung cancer xenograft model. A higher drug concentration within the gastrointestinal tract relative to plasma in preclinical models suggests potential to treat inflammatory bowel disease. Persistently activated STAT3 has been shown to be oncogenic, and drives expression of cellular proteins which contribute to central processes in cancer progression (survival, proliferation, invasion, angiogenesis). JAK1 is the key Janus kinase responsible for cytokine-mediated STAT3 activation. The chemical structure of AZD4205 matches that for the INN golidocitinib which was surfaced in WHO Proposed list 125 in July 2021.
iupac name: (2R)-N-[3-[2-[(3-methoxy-1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]-1H-indol-7-yl]-2-(4-methylpiperazin-1-yl)propanamide
synonym: AZD-4205
synonym: JAK1-IN-3
synonym: compound 21 [PMID: 32297743]
synonym: example 32 [US9714236B2]
synonym: AZD4205
approved: f
ligand name: golidocitinib
type: SyntheticOrganicLigand

NHWD-870
in ch i key: BBKUPPVLTRGWDN-GDLZYMKVSA-N
in ch i: InChI=1S/C29H29N7O/c1-18-28(35(3)33-32-18)21-15-25-27(30-16-21)26-22-17-31-34(2)23(22)9-10-24(26)36(25)29(19-7-5-4-6-8-19)20-11-13-37-14-12-20/h4-10,15-17,20,29H,11-14H2,1-3H3/t29-/m1/s1
comment: NHWD-870 is an orally bioavailable bromodomain and extra-terminal (BET) inhibitor, that exhibits selectivity for bromodomain containing 4 (BRD4) <Reference id=39037/>. It was developed for anti-cancer potential. In vitro, it is more potent than clinical stage BET inhibitors such as <Ligand id=8359/> (OTX-015) and <Ligand id=7033/> (GSK-525762). NHWD-870 potently reduces tumour growth in a number of different mouse models of cancers, including lung and ovarian tumours, lymphoma, and melanoma.
synonym: NHWD870
approved: f
ligand name: NHWD-870
type: SyntheticOrganicLigand

SKF-82958
canonical SMILES: C=CCN1CCc2c(C(C1)c1ccccc1)cc(c(c2Cl)O)O
isomeric SMILES: C=CCN1CCc2c(C(C1)c1ccccc1)cc(c(c2Cl)O)O
in ch i key: HJWHHQIVUHOBQN-UHFFFAOYSA-N
in ch i: InChI=1S/C19H20ClNO2/c1-2-9-21-10-8-14-15(11-17(22)19(23)18(14)20)16(12-21)13-6-4-3-5-7-13/h2-7,11,16,22-23H,1,8-10,12H2
comment: Dopamine D1 receptor agonist. SKF-82958 hydrobromide is a D1/D5 receptor full agonist.
iupac name: 6-chloro-1-phenyl-3-prop-2-enyl-1,2,4,5-tetrahydro-3-benzazepine-7,8-diol
xref: CHEMBL35354
synonym: SKF82958
synonym: SKF 82958
approved: f
ligand name: SKF-82958
type: SyntheticOrganicLigand

merimepodib
in ch i key: JBPUGFODGPKTDW-SFHVURJKSA-N
in ch i: InChI=1S/C23H24N4O6/c1-30-20-10-17(5-6-19(20)21-12-24-14-32-21)27-22(28)26-16-4-2-3-15(9-16)11-25-23(29)33-18-7-8-31-13-18/h2-6,9-10,12,14,18H,7-8,11,13H2,1H3,(H,25,29)(H2,26,27,28)/t18-/m0/s1
comment: Merimepodib is an orally bioavailable, non-competitive inhibitor of inosine monophosphate dehydrogenase (IMPDH) <Reference id=39023/>. It has antiviral activity, suppressing replication of Zika virus (ZIKV) <Reference id=39021/>, hepatitis C virus (HCV), and other emerging viral pathogens <Reference id=39020/>. IMPDH inhibition reduces intracellular guanine nucleotide levels, thus limiting RNA and DNA synthesis both for cellular proliferation, and for viral replication inside host cells. Experimental evidence shows that the activity of merimepodib can augment the anti-replicative effects of other antivirals such as <Ligand id=6842/> and T-705 (favipiravir).
xref: CHEMBL304087
synonym: VX-497
synonym: VX497
synonym: MMPD
approved: f
ligand name: merimepodib
type: SyntheticOrganicLigand

HM01
in ch i key: WGIAKIIMCPKJQN-SWLSCSKDSA-N
comment: HM01 is reported as a brain‐penetrating, orally bioavailable, ghrelin receptor agonist <Reference id=40472/>. It reduces motion‐induced emesis in a rodent model <Reference id=39019/>.
iupac name: 1‐[(1S)‐1‐(2,3‐dichloro‐4‐methoxyphenyl)ethyl]‐3‐methyl‐3‐[(4R)‐1‐methyl‐3,3‐dimethyl‐4‐piperidyl]urea
approved: f
ligand name: HM01
type: SyntheticOrganicLigand

PO-322
canonical SMILES: O=C1Nc2c(C1=NNc1nc3c(o1)cccc3)cccc2
isomeric SMILES: O=C1Nc2c(C1=NNc1nc3c(o1)cccc3)cccc2
in ch i key: NWUCBUGDPJNKAC-UHFFFAOYSA-N
in ch i: InChI=1S/C15H10N4O2/c20-14-13(9-5-1-2-6-10(9)16-14)18-19-15-17-11-7-3-4-8-12(11)21-15/h1-8H,(H,17,19)(H,16,18,20)
comment: PO-322 is an immunosuppressive compound. Its effects are mediated via inhibition of serum/glucocorticoid regulated kinase 1 (SGK1) <Reference id=39018/>. SGK1 is a downstream target of mTOR (a significant mediator involved the cell signalling that leads to T cell activation).
iupac name: 3-(1,3-benzoxazol-2-yldiazenyl)-1H-indol-2-ol
synonym: 1H-indole-2,3-dione 3-(1,3-benzoxazol-2-ylhydrazone)
synonym: PO322
approved: f
ligand name: PO-322
type: SyntheticOrganicLigand

GSK-189254
in ch i key: WROHEWWOCPRMIA-UHFFFAOYSA-N
in ch i: InChI=1S/C21H25N3O2/c1-22-21(25)17-6-8-20(23-14-17)26-19-7-5-15-9-11-24(18-3-2-4-18)12-10-16(15)13-19/h5-8,13-14,18H,2-4,9-12H2,1H3,(H,22,25)
comment: Potent and selective H3 histamine receptor inverse agonist. Radioligand 11C-GSK189254 can be used to quantify H3 receptor availability in humans in vivo using PET.
iupac name: 6-[(3-cyclobutyl-1,2,4,5-tetrahydro-3-benzazepin-8-yl)oxy]-N-methylpyridine-3-carboxamide
xref: CHEMBL517140
synonym: GSK189254
synonym: GSK-189,254
approved: f
ligand name: GSK-189254
type: SyntheticOrganicLigand

β-D-N4-hydroxycytidine
in ch i key: XCUAIINAJCDIPM-XVFCMESISA-N
in ch i: InChI=1S/C9H13N3O6/c13-3-4-6(14)7(15)8(18-4)12-2-1-5(11-17)10-9(12)16/h1-2,4,6-8,13-15,17H,3H2,(H,10,11,16)/t4-,6-,7-,8-/m1/s1
comment: Preliminary evidence indicates that the ribonucleoside analogue β-D-N4-hydroxycytidine (NHC, EIDD-1931) has broad spectrum antiviral activity against SARS-CoV-2, MERS-CoV, SARS-CoV, and related zoonotic group 2b or 2c Bat-CoVs <Reference id=1395/>. The potency of the NHC ester prodrug (<Ligand id=10737/>) against multiple coronaviruses, its therapeutic efficacy, and oral bioavailability in vivo, all highlight its potential utility as an effective antiviral against SARS-CoV-2 and other future zoonotic coronaviruses.
iupac name: 1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-(hydroxyamino)pyrimidin-2-one
xref: CHEMBL2178720
synonym: NHC
synonym: EIDD-1931
approved: f
ligand name: β-D-N4-hydroxycytidine
type: SyntheticOrganicLigand

garcinoic acid
canonical SMILES: C/C(=C/CC[C@]1(C)CCc2c(O1)c(C)cc(c2)O)/CC/C=C(/CC/C=C(/C(=O)O)/C)/C
isomeric SMILES: C/C(=C/CC[C@]1(C)CCc2c(O1)c(C)cc(c2)O)/CC/C=C(/CC/C=C(/C(=O)O)/C)/C
in ch i key: QOFWRHWADNWKSU-LRXIOGKNSA-N
in ch i: InChI=1S/C27H38O4/c1-19(11-7-13-21(3)26(29)30)9-6-10-20(2)12-8-15-27(5)16-14-23-18-24(28)17-22(4)25(23)31-27/h9,12-13,17-18,28H,6-8,10-11,14-16H2,1-5H3,(H,29,30)/b19-9+,20-12+,21-13+/t27-/m1/s1
comment: Garcinoic acid is a naturally occurring derivative of δ-tocotrienol, that is found in the seeds of Garcinia kola. It has been reported as a selective agonist of the pregnane X receptor <Reference id=39003/>.
iupac name: (2E,6E,10E)-13-[(2R)-6-hydroxy-2,8-dimethyl-3,4-dihydrochromen-2-yl]-2,6,10-trimethyltrideca-2,6,10-trienoic acid
synonym: tocotrienoloic acid
synonym: trans-delta-tocotrienoloic acid
approved: f
ligand name: garcinoic acid
type: NaturalProductLigand

I-432
in ch i key: LMPUOHRYPACLDR-IQHZPMLTSA-N
comment: I-432 is an inhibitor of the serine protease TMPRSS2 <Reference id=38991/>. TMPRSS2, present in human airway cells, is involved in processes that support infection by a number of viruses <Reference id=38992/>, thus inhibitors of this protease are being investigated for anti-viral potential.
iupac name: 3-[(2R)-3-[4-(2-aminoethyl)piperidin-1-yl]-2-[3-(4,6-dichlorocyclohexa-1,5-dien-1-yl)benzenesulfonamido]-3-oxopropyl]benzene-1-carboximidamide
synonym: I432
approved: f
ligand name: I-432
type: SyntheticOrganicLigand

compound 25 [PMID: 32105470]
in ch i key: XVPZEJHHJYHMIV-UHFFFAOYSA-N
comment: Compound 25 is the most efficacious glutathione transferase omega-1 (GSTO1-1) inhibitor of a number reported by Xie et al. (2020) <Reference id=38963/>. It is proposed as a pharmacological tool to interrogate cellular responses to GSTO1-1 inhibition.
iupac name: 2-Chloro-N-(3-(morpholinosulfonyl)-4-(trifluoromethyl)phenyl)acetamide
approved: f
ligand name: compound 25 [PMID: 32105470]
type: SyntheticOrganicLigand

otamixaban
in ch i key: PFGVNLZDWRZPJW-OPAMFIHVSA-N
in ch i: InChI=1S/C25H26N4O4/c1-16(22(25(31)33-2)15-17-4-3-5-21(14-17)23(26)27)28-24(30)20-8-6-18(7-9-20)19-10-12-29(32)13-11-19/h3-14,16,22H,15H2,1-2H3,(H3,26,27)(H,28,30)/t16-,22-/m1/s1
comment: Otamixaban (FXV673) is an anticoagulant that was originally reported by Aventis Pharmaceuticals (Sanofi) <Reference id=38989/>. It is a potent and selective direct inhibitor of coagulation factor Xa that is delivered intravenously. The INN record stipulates the (2R,3R) configuration. Virtual docking studies suggest that otamixaban may bind to the serine protease TMPRSS2 <Reference id=42401/><Reference id=42400/>, which is linked to host cell entry by a number of viruses, in particular influenza viruses and respiratory viruses such as SARS-CoV-2. Inhibition of TMPRSS2 is being examined for antiviral activity. The TMPRSS2 inhibitory activity of otamixaban is reported in <Reference id=42400/>.
iupac name: methyl (2R,3R)-2-[(3-carbamimidoylphenyl)methyl]-3-[[4-(1-oxidopyridin-1-ium-4-yl)benzoyl]amino]butanoate
xref: CHEMBL46618
synonym: FXV-673
synonym: FXV673
synonym: XRP-0673
synonym: XRP0673
synonym: compound 9c [PMID: 12039587]
approved: f
ligand name: otamixaban
type: SyntheticOrganicLigand

PD-144418
canonical SMILES: CCCN1CCC=C(C1)c1onc(c1)c1ccc(cc1)C
isomeric SMILES: CCCN1CCC=C(C1)c1onc(c1)c1ccc(cc1)C
in ch i key: FOQRKFCLRMMKAT-UHFFFAOYSA-N
in ch i: InChI=1S/C18H22N2O/c1-3-10-20-11-4-5-16(13-20)18-12-17(19-21-18)15-8-6-14(2)7-9-15/h5-9,12H,3-4,10-11,13H2,1-2H3
comment: PD-144418 is a σ1 receptor antagonist <Reference id=38984/>. It is selective for σ1 binding sites over σ2 binding sites in vitro.
xref: CHEMBL4088272
synonym: PD144418
approved: f
ligand name: PD-144418
type: SyntheticOrganicLigand

ABBV-744
in ch i key: OEDSFMUSNZDJFD-UHFFFAOYSA-N
in ch i: InChI=1S/C28H30FN3O4/c1-7-30-26(33)22-13-20-21(14-32(6)27(34)24(20)31-22)19-12-17(28(4,5)35)8-9-23(19)36-25-15(2)10-18(29)11-16(25)3/h8-14,31,35H,7H2,1-6H3,(H,30,33)
comment: ABBV-744 is an investigational, orally bioavailable BET family protein (BRD) inhibitor, that was developed for antiproliferative potential in cancer <Reference id=38983/>. It was designed to selectively target the BD2 domain of BET family proteins, in an effort to limit potential on-target adverse activity associated with BD1 interactions. In vivo, ABBV-744 produced fewer platelet and gastrointestinal toxicities than a dual BD1/2-targeting compound in preclinical models. Its antiproliferative effects are primarily evident in acute myeloid leukaemia cell lines and in prostate cancer cells that express the full-length androgen receptor (AR).
iupac name: N-ethyl-4-[2-(4-fluoro-2,6-dimethylphenoxy)-5-(2-hydroxypropan-2-yl)phenyl]-6-methyl-7-oxo-1H-pyrrolo[2,3-c]pyridine-2-carboxamide
xref: CHEMBL4297454
synonym: ABBV 744
synonym: ABBV744
approved: f
ligand name: ABBV-744
type: SyntheticOrganicLigand

ONO-7579
in ch i key: GYPOVJZOMXEUDO-UHFFFAOYSA-N
comment: Highly potent and selective pan-tropomyosin receptor kinase family (neurotrophic tyrosine receptor kinase; TRKA, TRKB, TRKC) inhibitor.
iupac name: 1-[2-[4-(2-amino-5-chloropyridin-3-yl)phenoxy]pyrimidin-5-yl]-3-[2-methylsulfonyl-5-(trifluoromethyl)phenyl]urea
xref: CHEMBL3892052
synonym: ONO7579
synonym: ONO 7579
approved: f
ligand name: ONO-7579
type: SyntheticOrganicLigand

MZ1
in ch i key: PTAMRJLIOCHJMQ-PYNGZGNASA-N
comment: MZ1 is a BRD2/4 bivalent degrader molecule (proteolysis-targeting chimera; PROTAC) <Reference id=38982/>. It conjugates a BRD BET domain-targeting warhead (derived from <Ligand id=7511/>) to an E3 ubiquitin ligase ligand (VH032, which binds the VHL ligase) via a linker. BET bromodomain protein degradation promotes a collapse of global elongation and a resultant antiproliferative effect. MZ1 is structurally similar to <Ligand id=10534/>.
xref: CHEMBL4226570
approved: f
ligand name: MZ1
type: SyntheticOrganicLigand

4F-MT-45
in ch i key: AGKZEOCNYCHVLW-UHFFFAOYSA-N
in ch i: InChI=1S/C24H31FN2/c25-22-13-11-21(12-14-22)24(19-20-7-3-1-4-8-20)27-17-15-26(16-18-27)23-9-5-2-6-10-23/h1,3-4,7-8,11-14,23-24H,2,5-6,9-10,15-19H2
comment: μ-opioid receptor agonist.
iupac name: 1-cyclohexyl-4-[1-(4-fluorophenyl)-2-phenylethyl]piperazine
approved: f
ligand name: 4F-MT-45
type: SyntheticOrganicLigand

3F-MT-45
in ch i key: CGVHPULMBGGZPI-UHFFFAOYSA-N
in ch i: InChI=1S/C24H31FN2/c25-22-11-7-10-21(19-22)24(18-20-8-3-1-4-9-20)27-16-14-26(15-17-27)23-12-5-2-6-13-23/h1,3-4,7-11,19,23-24H,2,5-6,12-18H2
comment: μ-opioid receptor agonist.
iupac name: 1-cyclohexyl-4-[1-(3-fluorophenyl)-2-phenylethyl]piperazine
approved: f
ligand name: 3F-MT-45
type: SyntheticOrganicLigand

2F-MT-45
canonical SMILES: Fc1ccccc1C(N1CCN(CC1)C1CCCCC1)Cc1ccccc1
isomeric SMILES: Fc1ccccc1C(N1CCN(CC1)C1CCCCC1)Cc1ccccc1
in ch i key: BZESPHAKQKJBSM-UHFFFAOYSA-N
in ch i: InChI=1S/C24H31FN2/c25-23-14-8-7-13-22(23)24(19-20-9-3-1-4-10-20)27-17-15-26(16-18-27)21-11-5-2-6-12-21/h1,3-4,7-10,13-14,21,24H,2,5-6,11-12,15-19H2
comment: μ-opioid receptor agonist.
iupac name: 1-cyclohexyl-4-[1-(2-fluorophenyl)-2-phenylethyl]piperazine
approved: f
ligand name: 2F-MT-45
type: SyntheticOrganicLigand

MT-45
in ch i key: IGBRRSIHEGCUEN-UHFFFAOYSA-N
in ch i: InChI=1S/C24H32N2/c1-4-10-21(11-5-1)20-24(22-12-6-2-7-13-22)26-18-16-25(17-19-26)23-14-8-3-9-15-23/h1-2,4-7,10-13,23-24H,3,8-9,14-20H2
comment: μ-opioid receptor agonist.
iupac name: 1-cyclohexyl-4-[1,2-di(phenyl)ethyl]piperazine
synonym: IC-6
synonym: MT45
synonym: NSC 299236
synonym: CDEP
approved: f
ligand name: MT-45
type: SyntheticOrganicLigand

PF-05089771
in ch i key: ZYSCOUXLBXGGIM-UHFFFAOYSA-N
comment: PF-05089771 is an aryl sulfonamide Nav1.7 channel blocker that binds to the inactivated state of Nav1.7 channels with high affinity but binds only weakly to channels in the resting state.
iupac name: 4-[2-(5-amino-1H-pyrazol-4-yl)-4-chlorophenoxy]-5-chloro-2-fluoro-N-(1,3-thiazol-4-yl)benzenesulfonamide
xref: CHEMBL2325014
synonym: PF05089771
synonym: PF 05089771
approved: f
ligand name: PF-05089771
type: SyntheticOrganicLigand

RO5256390
canonical SMILES: Cc1c([C@H]2COC(=N2)N)cccc1F
isomeric SMILES: Cc1c([C@H]2COC(=N2)N)cccc1F
in ch i key: IOHOUWIYOVWGHV-SECBINFHSA-N
in ch i: InChI=1S/C10H11FN2O/c1-6-7(3-2-4-8(6)11)9-5-14-10(12)13-9/h2-4,9H,5H2,1H3,(H2,12,13)/t9-/m1/s1
comment: RO5256390 is an orally available partial agonist that targets trace amine-associated receptor 1 (TAAR1).
iupac name: (4S)-4-(3-fluoro-2-methylphenyl)-4,5-dihydro-1,3-oxazol-2-amine
xref: CHEMBL3781694
synonym: RO-5256390
synonym: RO 5256390
approved: f
ligand name: RO5256390
type: SyntheticOrganicLigand

DRL-17822
in ch i key: OCNBSSLDAIWTKS-UHFFFAOYSA-N
in ch i: InChI=1S/C30H31F6N7/c1-18-4-3-5-22-12-23(27(37-26(18)22)42(14-19-6-7-19)15-20-8-9-20)17-43(28-38-40-41(2)39-28)16-21-10-24(29(31,32)33)13-25(11-21)30(34,35)36/h3-5,10-13,19-20H,6-9,14-17H2,1-2H3
comment: DRL-17822 is a cholesteryl ester transfer protein (CETP) inhibitor.
iupac name: 3-[[[3,5-bis(trifluoromethyl)phenyl]methyl-(2-methyltetrazol-5-yl)amino]methyl]-N,N-bis(cyclopropylmethyl)-8-methylquinolin-2-amine
synonym: DRL17822
synonym: DRL 17822
synonym: Example 57 [US20070015758A1]
approved: f
ligand name: DRL-17822
type: SyntheticOrganicLigand

compound 13b [PMID: 32198291]
in ch i key: FRACPXUHUTXLCX-BELIEFIBSA-N
in ch i: InChI=1S/C31H41N5O7/c1-31(2,3)43-30(42)35-22-10-7-15-36(29(22)41)24(16-19-11-12-19)27(39)34-23(17-21-13-14-32-26(21)38)25(37)28(40)33-18-20-8-5-4-6-9-20/h4-10,15,19,21,23-25,37H,11-14,16-18H2,1-3H3,(H,32,38)(H,33,40)(H,34,39)(H,35,42)/t21-,23-,24-,25+/m0/s1
comment: Compound 13b is an inhibitor of SARS-CoV-2 main protease (Mpro) <Reference id=38975/>. It is a derivative of the prevoiusly reported α-ketoamide inhibitor <Ligand id=10705/> <Reference id=38908/>. Compound 13b has an enhanced plasma half-life compared to 11r, plus it exhibits substantial lung tropism and has shown suitability for inhalation-mediated administration.
iupac name: Tert-butyl (1-((S)-1-(((S)-4-(benzylamino)-3,4-dioxo-1-((S)-2-oxopyrrolidin-3-yl)-butan-2-yl)ami-no)-3-cyclopropyl-1-oxopropan-2-yl)-2-oxo-1,2-dihydropyridin-3-yl)carbamate
approved: f
ligand name: compound 13b [PMID: 32198291]
type: SyntheticOrganicLigand

C1-27
canonical SMILES: ClCC(=O)Nc1ccc(c(c1)S(=O)(=O)N(C)C)Cl
isomeric SMILES: ClCC(=O)Nc1ccc(c(c1)S(=O)(=O)N(C)C)Cl
in ch i key: YEHYODCKTNLFQU-UHFFFAOYSA-N
comment: C1-27 is a small molecule inhibitor of glutathione transferase omega-1 (GSTO1-1) <Reference id=38962/>.
iupac name: 2-chloro-N-[4-chloro-3-(dimethylsulfamoyl)phenyl]acetamide
xref: CHEMBL4210652
synonym: GSTO1-IN-1
approved: f
ligand name: C1-27
type: SyntheticOrganicLigand

PSB-1584
canonical SMILES: CCCCCCNc1cc(=O)[nH]c(=O)[nH]1
isomeric SMILES: CCCCCCNc1cc(=O)[nH]c(=O)[nH]1
in ch i key: SDXQSUJXSHUIBQ-UHFFFAOYSA-N
in ch i: InChI=1S/C10H17N3O2/c1-2-3-4-5-6-11-8-7-9(14)13-10(15)12-8/h7H,2-6H2,1H3,(H3,11,12,13,14,15)
comment: PSB-1584 is a non-biased, high affinity agonist of the Gi protein-coupled receptor GPR84 <Reference id=34636/>. A radiolabelled version ([3H]PSB-1584; KD 2.08 nM) which effectively labels GPR84 in native cells and tissues has been synthesised <Reference id=38956/>.
iupac name: 6-(hexylamino)-1H-pyrimidine-2,4-dione
xref: CHEMBL124977
synonym: compound 20 [PMID: 30023867]
synonym: PSB1584
synonym: 6-hexylaminouracil
approved: f
ligand name: PSB-1584
type: SyntheticOrganicLigand

PN6047
in ch i key: ACDBSKNTCSNAAV-UHFFFAOYSA-N
in ch i: InChI=1S/C26H28N4O2S/c1-29(2)26(32)20-8-6-18(7-9-20)24(21-4-3-5-22(14-21)25(27)31)19-10-12-30(13-11-19)16-23-15-28-17-33-23/h3-9,14-15,17H,10-13,16H2,1-2H3,(H2,27,31)
comment: A G protein-biased and selective δ opioid agonist. In cell-based assays, PN6047 fully engages G protein signaling but is a partial agonist in both the arrestin recruitment and internalization assays.
iupac name: 3-[[4-(dimethylcarbamoyl)phenyl]-[1-(1,3-thiazol-5-ylmethyl)piperidin-4-ylidene]methyl]benzamide
approved: f
ligand name: PN6047
type: SyntheticOrganicLigand

PRD_002214
in ch i key: IDBWWEGDLCFCTD-NQJFWITJSA-N
in ch i: InChI=1S/C35H48N6O8/c1-20(2)16-27(39-35(47)30(21(3)4)40-31(43)23(6)37-34(46)28-17-22(5)49-41-28)33(45)38-26(18-25-14-15-36-32(25)44)12-13-29(42)48-19-24-10-8-7-9-11-24/h7-13,17,20-21,23,25-27,30H,14-16,18-19H2,1-6H3,(H,36,44)(H,37,46)(H,38,45)(H,39,47)(H,40,43)/b13-12-/t23-,25-,26+,27-,30-/m0/s1
comment: PRD_002214 is an irreversible peptide-like inhibitor of the main protease (MPRO) of SARS-CoV-2 <Reference id=38968/>. The chemical structure was obtained from the RCSB Protein Data Bank entry 6LU7 which shows the ligand in complex with the protease. The article describing the work has not yet been published (March 12, 2020), but the inhibitor (also referred to as N3) has been deployed in other MPRO crystallisation studies <Reference id=38951/>. The MPRO sequence is held in the NCBI record 'Chain A, SARS-CoV-2 main protease'.
iupac name: benzyl (2Z,4S)-4-[(2S)-4-methyl-2-[(2S)-3-methyl-2-[(2S)-2-[(5-methyl-1,2-oxazol-3-yl)formamido]propanamido]butanamido]pentanamido]-5-[(3S)-2-oxopyrrolidin-3-yl]pent-2-enoate
synonym: inhibitor N3
synonym: N-[(5-METHYLISOXAZOL-3-YL)CARBONYL]ALANYL-L-VALYL-N~1~-((1R,2Z)-4-(BENZYLOXY)-4-OXO-1-{[(3R)-2-OXOPYRROLIDIN-3-YL]METHYL}BUT-2-ENYL)-L-LEUCINAMIDE
approved: f
ligand name: PRD_002214
type: SyntheticOrganicLigand

remdesivir
in ch i key: RWWYLEGWBNMMLJ-YSOARWBDSA-N
in ch i: InChI=1S/C27H35N6O8P/c1-4-18(5-2)13-38-26(36)17(3)32-42(37,41-19-9-7-6-8-10-19)39-14-21-23(34)24(35)27(15-28,40-21)22-12-11-20-25(29)30-16-31-33(20)22/h6-12,16-18,21,23-24,34-35H,4-5,13-14H2,1-3H3,(H,32,37)(H2,29,30,31)/t17-,21+,23+,24+,27-,42-/m0/s1
comment: Remdesivir (GS-5734) is a nucleotide analogue drug that was developed by Gilead Sciences for antiviral potential, in particular for anti-Ebola and anti-Marburg virus activity <Reference id=38940/>. It acts is an inhibitor of the viral RNA-dependent RNA polymerase (RdRP) that functions as a chain terminator during viral RNA synthesis. Remdesivir is a prodrug whose major active metabolite is <Ligand id=11445/>. Its 1'-CN group and C-linked nucleobase ensure optimal anti-Ebola potency and selectivity against host polymerase enzymes. Remdesivir has broad-spectrum activity against several viral families such as filoviruses, paramyxoviruses, and coronaviruses, and including the SARS and MERS coronaviruses (CoVs), endemic circulating human CoVs, and against SARS-CoV-2 <Reference id=38941/><Reference id=38942/><Reference id=39978/>. The first patient to test positive for SARS-CoV-2 in the US was treated with i.v. remdesivir (using compassionate use of an investigational therapy prescribing) and his clinical condition improved significantly within the next 24h without observation of adverse effects <Reference id=38943/>.
iupac name: 2-ethylbutyl (2S)-2-[[[(2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxyoxolan-2-yl]methoxy-phenoxyphosphoryl]amino]propanoate
xref: CHEMBL4065616
synonym: compound 4b [PMID: 28124907]
synonym: GS5734
synonym: Veklury®
synonym: GS-5734
approved: t
ligand name: remdesivir
type: SyntheticOrganicLigand

aloxistatin
in ch i key: SRVFFFJZQVENJC-IHRRRGAJSA-N
in ch i: InChI=1S/C17H30N2O5/c1-6-23-17(22)14-13(24-14)16(21)19-12(9-11(4)5)15(20)18-8-7-10(2)3/h10-14H,6-9H2,1-5H3,(H,18,20)(H,19,21)/t12-,13-,14-/m0/s1
comment: Aloxistatin (EP-453) is an irreversible inhibitor of the cysteine protease cathepsin B and calpains 1 and 2 <Reference id=38938/>. It acts by alkylating the catalytic cysteine thiol <Reference id=38939/>. In cellular assays it inhibits autophagy and lysosomal function.
iupac name: ethyl (2S,3S)-3-[[(2S)-4-methyl-1-(3-methylbutylamino)-1-oxopentan-2-yl]carbamoyl]oxirane-2-carboxylate
xref: CHEMBL63440
synonym: E-64d
synonym: EP453
synonym: loxistatin
synonym: E64d
synonym: compound 2b [PMID: 8765519]
approved: f
ligand name: aloxistatin
type: SyntheticOrganicLigand

compound 16 [PMID: 31653597]
in ch i key: BOAJXEFAPWTSFX-FXASYPJLSA-N
comment: Compound 16 is a hybrid, hetero-bifunctional molecule that comprises a PCSK9-binding ligand connected to an Arg(Boc)3 moiety <Reference id=38679/>. This latter motif acts as a ubiquitin-independent proteasome-recruiting element <Reference id=38923/><Reference id=38924/><Reference id=38925/> that in this case was used to facilitate ligand-induced degradation of PCSK9 protein. X-ray co-crystallisation shows that compound 16 binds to an allosteric site on PCSK9 and has no intrinsic effect on PCSK9 function. The X-ray structure also reveals that the Arg(Boc)3 moiety extents outwith the binding pocket which enables interactions with components of the degradation complex. Targeted degradation of PCSK9 is being examined as an alternative to anti-PCSK9 monoclonals (already in the clinic) or small-molecule inhibitors of the PCSK9/low-density lipoprotein (LDL) receptor protein-protein interaction (which is very difficult to drug due to the 3D structure of the interaction domains) as a novel mechanism to decrease LDL cholesterol levels. The Arg(Boc)3 motif is used as an alternative to the more widely utilised ubiquitin-proteasome system recruiting elements that engage the VHL and CRBN ubiquitin ligases, and which have been used in a number of previously reported PROTACs.
iupac name: 4-[4-[[(1R)-6-[2-[2-[[(2S)-5-[bis[(2-methylpropan-2-yl)oxycarbonylamino]methylideneamino]-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoyl]amino]ethoxy]ethoxy]-1-methyl-1-[2-oxo-2-(1,3-thiazol-2-ylamino)ethyl]-3,4-dihydro-2H-isoquinolin-7-yl]oxy]-2-fluorophenyl]benzoic acid
approved: f
ligand name: compound 16 [PMID: 31653597]
type: SyntheticOrganicLigand

MK-7622
in ch i key: JUVQLZBJFOGEEO-GOTSBHOMSA-N
in ch i: InChI=1S/C25H25N3O2/c1-16-10-11-17(14-26-16)12-18-13-21-24(20-7-3-2-6-19(18)20)27-15-28(25(21)30)22-8-4-5-9-23(22)29/h2-3,6-7,10-11,13-15,22-23,29H,4-5,8-9,12H2,1H3/t22-,23-/m0/s1
comment: MK-7622 is a high cooperativity positive allosteric modulator of the M1 muscarinic acetylcholine receptor (M1R) <Reference id=38919/><Reference id=38921/><Reference id=38922/>. Clinical development of MK-7622 as a therapy for neurological and cognitive disorders was terminated at Phase 2.
iupac name: 3-[(1S,2S)-2-hydroxycyclohexyl]-6-[(6-methylpyridin-3-yl)methyl]benzo[h]quinazolin-4-one
xref: CHEMBL4078588
synonym: MK7622
approved: f
ligand name: MK-7622
type: SyntheticOrganicLigand

T‐495
in ch i key: BWJHJLINOYAPEG-HOTGVXAUSA-N
comment: T-495 is a positive allosteric modulator (PAM) of the M1 muscarinic acetylcholine receptor <Reference id=38919/>. It was designed as a low-cooperativity PAM which was predicted to reduce the gastrointestinal (GI) side-effects (principally diarrhea) that are caused by M1R activation in the ileum, whilst retaining efficacy to improve cognitive deficits in animal models. The measure of allosteric cooperativity (α-value) of T-495 is 199. In contrast the α-value for <Ligand id=10712/> is 511, indicating that this PAM more effectively increases agonist activity at the receptor than T-495. In vivo, T‐495 exhibits a wider margin between memory improvement and induction of diarrhea than MK‐7622 in rats, suggesting that the hypothesis re low PAM cooperativity and reduced GI adverse reaction was valid. T-495 effectively reverses memory deficits in a mouse model of dementia with Lewy bodies and Parkinson's disease in which acetylcholine levels are reduced.
iupac name: 8-chloro-6-[(6-chloropyridin-3-yl)methyl]-3-[(1S,2S)-2-hydroxycyclopentyl]-7-methyl-2H-1,3-benzoxazin-4-one
synonym: example 24 [WO2016208775]
synonym: T495
approved: f
ligand name: T‐495
type: SyntheticOrganicLigand

iptacopan
in ch i key: RENRQMCACQEWFC-UGKGYDQZSA-N
in ch i: InChI=1S/C25H30N2O4/c1-4-31-19-10-12-27(22(14-19)17-5-7-18(8-6-17)25(28)29)15-21-20-9-11-26-24(20)16(2)13-23(21)30-3/h5-9,11,13,19,22,26H,4,10,12,14-15H2,1-3H3,(H,28,29)/t19-,22-/m0/s1
comment: Iptacopan (LNP023) is a small molecuile, orally bioavailable complement factor B inhibitor <Reference id=38917/><Reference id=38918/>. Factor B is a serine protease, that is a component of the alternative pathway (AP) of the complement system. The AP acts as an amplification loop of complement activation and contributes to various human diseases. Inhibition of factor B is being expolited as a mechanism to treat complement-mediated conditions such as C3 glomerulopathy (glomerulonephritis, including IgA nephropathy), paroxysmal nocturnal hemoglobinuria and atypical hemolytic uremic syndrome.
iupac name: 4-[(2S,4S)-4-ethoxy-1-[(5-methoxy-7-methyl-1H-indol-4-yl)methyl]piperidin-2-yl]benzoic acid
synonym: LNP-023
synonym: compound 41 [PMID: 32073845]
synonym: LNP023
approved: f
ligand name: iptacopan
type: SyntheticOrganicLigand

WF-47-JS03
in ch i key: YRBWLEAMGAGYBK-UHFFFAOYSA-N
in ch i: InChI=1S/C30H38N6O2/c1-29(2)16-21(17-30(3,4)35(29)5)33-27-25(19-11-9-8-10-12-19)26(31)36-28(34-27)22(18-32-36)20-13-14-23(37-6)24(15-20)38-7/h8-15,18,21H,16-17,31H2,1-7H3,(H,33,34)
comment: WF-47-JS03 is a RET (REarranged during Transfection) kinase inhibitor that was designed for anti-cancer potential <Reference id=38912/>. It is orally bioavailable, but was not well tolerated in mice at higher doses, indicating a narrow therapeutic window.
iupac name: 3-(3,4-dimethoxyphenyl)-N5-(1,2,2,6,6-pentamethylpiperidin-4-yl)-6-phenylpyrazolo[1,5-a]pyrimidine-5,7-diamine
synonym: compound 1 [Mathison et al., 2020]
synonym: WF47JS03
approved: f
ligand name: WF-47-JS03
type: SyntheticOrganicLigand

SI306
in ch i key: TWWILBWAYDXBCM-UHFFFAOYSA-N
comment: SI306 is a Src kinase inhibitor that was developed for activity against glioblastoma multiforme (GBM) <Reference id=38911/>.
iupac name: N-(3-bromophenyl)-1-(2-chloro-2-phenylethyl)-6-(2-morpholin-4-ylethylsulfanyl)pyrazolo[3,4-d]pyrimidin-4-amine
xref: CHEMBL3394092
approved: f
ligand name: SI306
type: SyntheticOrganicLigand

AB680
in ch i key: MFYLCAMJNGIULC-KCVUFLITSA-N
comment: AB680 is a reversible, slow-onset competitive inhibitor of CD73 (ecto-5'-nucleotidase) <Reference id=38910/>.
iupac name: [[(2R,3S,4R,5R)-5-[6-chloro-4-[[(1S)-1-(2-fluorophenyl)ethyl]amino]pyrazolo[3,4-b]pyridin-1-yl]-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]methylphosphonic acid
synonym: AB-680
approved: f
ligand name: AB680
type: SyntheticOrganicLigand

compound 15 [PMID: 32045236]
in ch i key: OJRUSAPKCPIVBY-KQYNXXCUSA-N
comment: Compound 15 is a small molecule, ADP analogue-based CD73 (ecto-5'-nucleotidase) inhibitor <Reference id=38909/>. Mechanisms to inhibit CD73 activity are being exploited for immuno-oncology potential, and are exemplified by the progress of the anti-CD73 monoclonal <Ligand id=9596/> and the small molecule inhibitor <Ligand id=10707/> into clinical trials as treatments for advanced solid tumours.
iupac name: 2-Iodoadenosine-5′-O-[(phosphonomethyl)phosphonic Acid]
approved: f
ligand name: compound 15 [PMID: 32045236]
type: SyntheticOrganicLigand

compound 11r [PMID: 32045235]
in ch i key: QTGORSKTHIBLJT-FIVJMQNTSA-N
in ch i: InChI=1S/C33H40N4O5/c38-29(17-16-23-10-4-1-5-11-23)36-28(20-24-12-6-2-7-13-24)32(41)37-27(21-26-18-19-34-31(26)40)30(39)33(42)35-22-25-14-8-3-9-15-25/h1,3-5,8-11,14-17,24,26-28H,2,6-7,12-13,18-22H2,(H,34,40)(H,35,42)(H,36,38)(H,37,41)/b17-16+/t26-,27-,28-/m0/s1
comment: Compound 11r is a peptidomimetic α-ketoamide that was designed for antiviral activity against corona- and enteroviruses <Reference id=38908/>. This study was posted to the BioRxiv preprint server <Reference id=38916/> prior to certification by peer review and publication in J. Med. Chem. The proteases that are essential for viral polyprotein processing by the corona- and enteroviruses exhibit a strong preference for substrates containing Gln at P1 position, and share an active-site conformation that engages the substrate's P1 residue. Compound 11r targets this unique P1-binding position within the active-sites of the main coronavirus protease and the enterovirus 3C protease. A crystal structure of 11r bound to the human SARS-CoV main protease has been submitted to the RSCB Protein Data Bank with accession ID 5N5O. UniProt P0C6X7 provides details of SARS-CoV proteins.
iupac name: (S)-N-Benzyl-3-((S)-2-cinnamamido-3-cyclohexylpropanamido)-2-oxo-4-((S)-2-oxopyrrolidin-3-yl)butanamide
synonym: Cinnamoyl-cyclopropylalanine-GlnLactam-CO-CO-NH-benzyl
approved: f
ligand name: compound 11r [PMID: 32045235]
type: SyntheticOrganicLigand

rimegepant
in ch i key: KRNAOFGYEFKHPB-ANJVHQHFSA-N
in ch i: InChI=1S/C28H28F2N6O3/c29-20-6-1-4-17(23(20)30)18-8-9-22(25-19(24(18)31)5-2-12-32-25)39-28(38)35-14-10-16(11-15-35)36-21-7-3-13-33-26(21)34-27(36)37/h1-7,12-13,16,18,22,24H,8-11,14-15,31H2,(H,33,34,37)/t18-,22+,24-/m0/s1
comment: Rimegepant (BMS-927711, BHV-3000) is a small molecule calcitonin gene-related peptide (CGRP) receptor antagonist <Reference id=38907/>.
iupac name: [(5S,6S,9R)-5-amino-6-(2,3-difluorophenyl)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-9-yl]4-(2-oxo-3H-imidazo[4,5-b]pyridin-1-yl)piperidine-1-carboxylate
xref: CHEMBL2178422
synonym: BMS-927711
synonym: BMS927711
synonym: BHV-3000
synonym: BHV3000
synonym: Nurtec ODT®
synonym: compound 8 [PMID: 23153230]
synonym: Vydura®
approved: t
ligand name: rimegepant
type: SyntheticOrganicLigand

SU-3327
canonical SMILES: [O-][N+](=O)c1cnc(s1)Sc1nnc(s1)N
isomeric SMILES: [O-][N+](=O)c1cnc(s1)Sc1nnc(s1)N
in ch i key: NQQBNZBOOHHVQP-UHFFFAOYSA-N
in ch i: InChI=1S/C5H3N5O2S3/c6-3-8-9-5(14-3)15-4-7-1-2(13-4)10(11)12/h1H,(H2,6,8)
comment: SU3327 was originally identified as an inhibitor of the serine/threonine c-Jun N-terminal kinases (JNKs) <Reference id=38905/>. It is substrate competitive (inhibiting the protein-protein interaction between JNK and the substrate JIP-1), and selective for JNK vs. p38 MAPK and Akt. SU3327 was shown to restore insulin sensitivity in mouse models of diabetes. In the search for new antibacterials, artificial intelligence algorithms were used to identify novel chemotypes that were likely to have novel mechanisms of antibacterial activity. SU3327 (re-named as halicin) was identified by this process and in vitro and in vivo follow-up showed that it potently killed a wide range of diffucult to treat, antibacterial-resistant bacterial strains <Reference id=38906/>. Halicin appears to disrupt the ability of bacteria to maintain an electrochemical gradient across their cell membranes which blocks their production of ATP for energy.
iupac name: 5-[(5-nitro-1,3-thiazol-2-yl)sulfanyl]-1,3,4-thiadiazol-2-amine
xref: CHEMBL510038
synonym: SU3327
synonym: halicin
synonym: compound 9 [PMID: 19271755]
approved: f
ligand name: SU-3327
type: SyntheticOrganicLigand

compound 5 [PMID: 30894487]
in ch i key: PJBRCGHQNUWERQ-UHFFFAOYSA-N
in ch i: InChI=1S/C17H16F3NO4/c18-10-1-2-13-11(7-10)12(22)8-14(25-13)15(23)21-9-16(24)3-5-17(19,20)6-4-16/h1-2,7-8,24H,3-6,9H2,(H,21,23)
comment: Compound 5 is the lead identified from a target-based approach to develop new compounds with antimalarial activity <Reference id=37837/>. The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
iupac name: N-[(4,4-difluoro-1-hydroxycyclohexyl)methyl]-6-fluoro-4-oxochromene-2-carboxamide
xref: CHEMBL3989220
approved: f
ligand name: compound 5 [PMID: 30894487]
type: SyntheticOrganicLigand

compound 15a [PMID: 32069401]
in ch i key: LSPJWTULWKYRTQ-UHFFFAOYSA-N
comment: Compound 15a is a dual phosphoinositide 3-kinase (PI3K)/mammalian target of rapamycin (mTOR) inhibitor that was designed for potential anti-tumour activity <Reference id=38904/>. Dysregulation of the PI3K-Akt-mTOR signalling pathway is often observed in cancers, and simultaneous inhibition of PI3K and mTOR is predicted to offer improved antitumour activity compared to drugs that target single components of the pathway. A number of dual PI3K/mTOR inhibitors are in clinical development (for example <Ligand id=7940/>, <Ligand id=8383/>, <Ligand id=7888/>, <Ligand id=8918/> and <Ligand id=8974/>). All of these inhibitors are associated with adverse effects. Compound 15a was designed to address issues around selectivity and toxicity. Unfortunately 15a produced hepatic toxicity in vivo, so further optimisation would be essential to identify a more suitable derivative.
iupac name: 2,4-Difluoro-N-(2-methoxy-5-(3-(5-(2-(4-methylpiperazin-1-yl)ethyl)-1,3,4-oxadiazol-2-yl)imidazo[1,2-a]pyridin-6-yl)pyridin-3-yl)benzenesulfonamide
approved: f
ligand name: compound 15a [PMID: 32069401]
type: SyntheticOrganicLigand

compound 3 [Uddin et al., 2020]
in ch i key: SRMUEFRMPPZYOH-UHFFFAOYSA-N
in ch i: InChI=1S/C20H19ClN2O/c1-13-20-17(9-10-22-13)18-11-16(24-2)7-8-19(18)23(20)12-14-3-5-15(21)6-4-14/h3-8,11H,9-10,12H2,1-2H3
comment: Compound 3 is reported as a substrate selective inhibitor of cyclooxygenase-2 (COX-2) <Reference id=38903/>. It preferentially inhibits conversion (by oxygenation) of the endocannabinoid 2-arachidonoylglycerol (2-AG) to prostaglandin glyceryl ester (PG-G) compared to oxygenation of arachidonic acid (AA) into prostaglandins, which is predicted to increase endocannabinoid levels in the brain and mediate anti-stress/anti-anxiety effects.
iupac name: 9-[(4-chlorophenyl)methyl]-6-methoxy-1-methyl-3H,4H,9H-pyrido[3,4-b]indole
approved: f
ligand name: compound 3 [Uddin et al., 2020]
type: SyntheticOrganicLigand

SUVN-911
canonical SMILES: Clc1ccc(cn1)OCC1CC2C(N1)C2
isomeric SMILES: Clc1ccc(cn1)OCC1CC2C(N1)C2
in ch i key: PYSCVJMLJRHJGJ-UHFFFAOYSA-N
in ch i: InChI=1S/C11H13ClN2O/c12-11-2-1-9(5-13-11)15-6-8-3-7-4-10(7)14-8/h1-2,5,7-8,10,14H,3-4,6H2
comment: SUVN-911 is a novel, potent, selective and orally active antagonist of neuronal α4β2 nicotinic acetylcholine receptors <Reference id=38902/>. It was designed by scientists at Suven Life Sciences as a potential anti-depressant drug. The disclosure report specifies the compound as the hydrochloride salt, so bioactivity data will have been generated using this form. We show the structure for the parent molecule in this entry.
iupac name: 3-[(6-chloropyridin-3-yl)oxymethyl]-2-azabicyclo[3.1.0]hexane
synonym: compound 9h [PMID: 32026697]
approved: f
ligand name: SUVN-911
type: SyntheticOrganicLigand

CSTI-300
in ch i key: WHLXDRXTKZLGFK-OAHLLOKOSA-N
in ch i: InChI=1S/C17H20N4O/c22-17-12-2-1-3-13-16(12)14(19-18-13)6-9-21(17)15-10-20-7-4-11(15)5-8-20/h1-3,11,15H,4-10H2,(H,18,19)/t15-/m1/s1
comment: 5-HT3 receptor partial agonist with potential to treat patients with irritable bowel syndrome or carcinoid syndrome.
approved: f
ligand name: CSTI-300
type: SyntheticOrganicLigand

KPR-5714
in ch i key: UEPRFRHXFVOHAM-LJQANCHMSA-N
in ch i: InChI=1S/C22H18F4N6O2/c23-14-6-4-13(5-7-14)17-10-18(31-30-17)20-15(2-1-3-16(20)24)21(34)29-19(22(25,26)12-33)11-32-27-8-9-28-32/h1-10,19,33H,11-12H2,(H,29,34)(H,30,31)/t19-/m1/s1
comment: Selective Transient Receptor Potential Melastatin 8 (TRPM8) antagonist.
synonym: KPR5714
synonym: KPR 5714
approved: f
ligand name: KPR-5714
type: SyntheticOrganicLigand

NCGC607
in ch i key: HFVDMJQQAKLUSN-UHFFFAOYSA-N
in ch i: InChI=1S/C24H22IN3O4/c1-28(19-7-3-2-4-8-19)23(30)15-26-24(31)20-9-5-6-10-21(20)32-16-22(29)27-18-13-11-17(25)12-14-18/h2-14H,15-16H2,1H3,(H,26,31)(H,27,29)
comment: NCGC607 is a glucocerebrosidase (GCase) chaperone <Reference id=38893/>. Unlike <Ligand id=10692/>, it does not occlude the enzyme active site so is not predicted to inhibit GCase activity. Enhancement of lysosomal GCase activity using chaperone molecules is being explored in diseases that are associated with mutant GCase GBA1, such as the lysosomal storage disorder Gaucher disease, and the neurodegenerative synucleinopathies Parkinson's disease and dementia with Lewy bodies. Enhanced GCase activity is predicted to prevent aggregation of neurotoxic proteins or improve the clearance of protein aggregates. This mechanism is considered to be applicable to a number of age-related neurodegenerative disorders that are characterised by aggregates of misfolded, non-functional and neurotoxic proteins <Reference id=38894/>. Under experimental conditions, NCGC607 restores GCase activity and protein levels, and reduces glycolipid storage in Gaucher macrophages, and reduces α-synuclein levels in dopaminergic neurons from Parkinson's patients <Reference id=38893/>.
synonym: KUC107647N
synonym: NCGC00241607
approved: f
ligand name: NCGC607
type: SyntheticOrganicLigand

AXT914
in ch i key: ALANRBCCCQEPFZ-UHFFFAOYSA-N
in ch i: InChI=1S/C29H23BrN4O2/c1-4-13-36-22-10-12-26-23(15-22)28(21-8-6-20(7-9-21)18(2)3)33-29(35)34(26)17-19-5-11-24-25(14-19)31-16-27(30)32-24/h1,5-12,14-16,18H,13,17H2,2-3H3
comment: AXT914 is a calcium-sensing receptor (CaSR) modulator that was developed by Novartis as a small molecule calcilytic <Reference id=38891/>. It is structurally related to the CaSR negative allosteric modulator (NAM) <Ligand id=9475/>. It acts to promote a rapid and transient release of parathyroid hormone. CaSR antagonists/NAMs are being investigated as bone-forming osteoporosis therapeutics.
iupac name: 1-[(2-bromoquinoxalin-6-yl)methyl]-4-(4-propan-2-ylphenyl)-6-prop-2-ynoxyquinazolin-2-one
synonym: AXT-914
approved: f
ligand name: AXT914
type: SyntheticOrganicLigand

sovesudil
in ch i key: PNWBYIFLWUCWKS-UHFFFAOYSA-N
in ch i: InChI=1S/C23H22FN3O3/c1-2-10-30-23(29)17-5-3-4-15(11-17)19-12-16(6-7-18(19)13-25)22(28)27-21-8-9-26-14-20(21)24/h3-9,11-12,14H,2,10,13,25H2,1H3,(H,26,27,28)
comment: Sovesudil (compound 18 [PMID: 24119557]) is a Rho-associated, coiled coil containing protein kinase (ROCK) inhibitor from Amakem Therapeutics <Reference id=38886/>. It contains a carboxylic ester moiety that is intended to facilitate rapid inactivation by esterases in vivo, as a mechanism to reduce systemic or local ROCK-associated side effects. This approach of exploiting designed metabolic inactivation is used to produce so-called 'soft' drugs. Compound 18's chemical structure matches that submitted to the WHO for INN sovesudil. Compound 18 is intended as an intraocular pressure (IOP)-lowering agent, and is expected to be devoid of the systemic blood pressure lowering side effect that is associated with systemic exposure to <Ligand id=5181/> and therefore precludes fasudil's use in non-cardiovascular indications <Reference id=38887/>. It is also expected to cause less local hyperemia than older ROCK inhibitor chemotypes. See our entry for <Ligand id=10498/>, which is another soft ROCK inhibitor from Amakem Therapeutics.
iupac name: propyl 3-[2-(aminomethyl)-5-[(3-fluoropyridin-4-yl)carbamoyl]phenyl]benzoate
xref: CHEMBL2440750
synonym: compound 18 [PMID: 24119557]
synonym: PHP-201
synonym: PHP201
synonym: AMA 0076
synonym: AMA0076
synonym: AMA-0076
approved: f
ligand name: sovesudil
type: SyntheticOrganicLigand

BNC375
in ch i key: LWWDCTBUJUEFDE-CRAIPNDOSA-N
comment: BNC375 is a potent, selective, and orally available type I positive allosteric modulator of α7 nicotinic acetylcholine receptor (nAChR).
iupac name: 4-[(1R,3R)-3-[(5-chloro-2-methoxyanilino)methyl]-2,2-dimethylcyclopropyl]benzenesulfonamide
synonym: HY-128575
synonym: CS-0095916
approved: f
ligand name: BNC375
type: SyntheticOrganicLigand

ambroxol
canonical SMILES: OC1CCC(CC1)NCc1cc(Br)cc(c1N)Br
isomeric SMILES: OC1CCC(CC1)NCc1cc(Br)cc(c1N)Br
in ch i key: JBDGDEWWOUBZPM-UHFFFAOYSA-N
in ch i: InChI=1S/C13H18Br2N2O/c14-9-5-8(13(16)12(15)6-9)7-17-10-1-3-11(18)4-2-10/h5-6,10-11,17-18H,1-4,7,16H2
comment: Ambroxol stimulates the synthesis and release of surfactant in the respiratory tract and acts as a mucoactive/expectorant drug. This action appears to be associated with ambroxol's regulation of glucosylceramide levels, via modulation of non-lysosomal glucosylceramidase (GCase) beta 2 (GBA2; Q9HCG7). Ambroxol is reported to act as a small molecule chaperone for GCase proteins that can increase the stability and function of mutant and wild-type GCases in in vitro and in vivo models <Reference id=38868/><Reference id=38869/><Reference id=33933/><Reference id=38870/><Reference id=38871/>, and in clinical trial subjects <Reference id=38872/><Reference id=38873/>. Ambroxol binds to nascent GCase proteins (at the enzyme active site) within the endoplasmic reticulum, and this action facilitates transport to the lysosome <Reference id=38878/><Reference id=38869/>. The acidic lysosomal environment provokes ambroxol dissassociation, leaving the enzyme free to function normally. SARS-CoV-2 and COVID-19: Evidence presented in a preprint suggests that ambroxol (and its prodrug <Ligand id=11218/>) directly disrupts the protein-protein interaction between the SARS-CoV-2 spike protein and ACE2 <Reference id=41114/>. This action is reported to inhibit the cytopathic effects induced by SARS-CoV-2 infection in vitro, which is suggestive of potential prophylactic and/or therapeutic use of these drugs against COVID-19.
iupac name: 4-[(2-amino-3,5-dibromophenyl)methylamino]cyclohexan-1-ol
xref: CHEMBL1477775
approved: t
ligand name: ambroxol
type: SyntheticOrganicLigand

roflupram
canonical SMILES: CC(CC(=O)c1ccc(c(c1)OC1COCC1)OC(F)F)C
isomeric SMILES: CC(CC(=O)c1ccc(c(c1)OC1COCC1)OC(F)F)C
in ch i key: IXURVUHDDXFYDR-UHFFFAOYSA-N
in ch i: InChI=1S/C16H20F2O4/c1-10(2)7-13(19)11-3-4-14(22-16(17)18)15(8-11)21-12-5-6-20-9-12/h3-4,8,10,12,16H,5-7,9H2,1-2H3
comment: Roflupram is a potent phosphodiesterase 4 (PDE4) inhibitor.
iupac name: 1-[4-(difluoromethoxy)-3-(oxolan-3-yloxy)phenyl]-3-methylbutan-1-one
synonym: FFPM
synonym: Zl-n-91
approved: f
ligand name: roflupram
type: SyntheticOrganicLigand

naporafenib
in ch i key: UEPXBTCUIIGYCY-UHFFFAOYSA-N
in ch i: InChI=1S/C25H25F3N4O4/c1-16-2-3-19(30-24(34)17-4-5-29-21(12-17)25(26,27)28)15-20(16)18-13-22(32-6-9-35-10-7-32)31-23(14-18)36-11-8-33/h2-5,12-15,33H,6-11H2,1H3,(H,30,34)
comment: Naporafenib (LXH254) is an investigational, potent, selective and orally bioavailable RAF inhibitor that was designed to target RAS mutant cancers, i.e.those that harbour genetic alterations in the RAS-RAF-MEK-ERK (MAPK) pathway <Reference id=38737/>. It is one of the compounds claimed in Novartis' patent WO2014151616A1 <Reference id=38738/>. Naporafenib is a Type-2 kinase inhibitor that binds the DFG-out conformation of the kinase.
iupac name: N-[3-[2-(2-hydroxyethoxy)-6-morpholin-4-ylpyridin-4-yl]-4-methylphenyl]-2-(trifluoromethyl)pyridine-4-carboxamide
synonym: compound 15 [PMID: 31059256]
synonym: LXH-254
synonym: example 1156 [WO2014151616A1]
synonym: LXH254
approved: f
ligand name: naporafenib
type: SyntheticOrganicLigand

JD5037
canonical SMILES: Clc1ccc(cc1)C1=NN(C[C@@H]1c1ccccc1)/C(=N/[C@H](C(=O)N)C(C)C)/NS(=O)(=O)c1ccc(cc1)Cl
isomeric SMILES: Clc1ccc(cc1)C1=NN(C[C@@H]1c1ccccc1)/C(=N/[C@H](C(=O)N)C(C)C)/NS(=O)(=O)c1ccc(cc1)Cl
in ch i key: GTCSIQFTNPTSLO-RPWUZVMVSA-N
comment: JD5037 is a peripherally restricted (PR) cannabinoid-1 receptor blocker (CB1R antagonist).
synonym: JD-5037
synonym: JD5037
approved: f
ligand name: JD5037
type: SyntheticOrganicLigand

AZ7188
canonical SMILES: O=CN1c2ccccc2CC1c1c[nH]c2c1cccc2
isomeric SMILES: O=CN1c2ccccc2CC1c1c[nH]c2c1cccc2
in ch i key: GFACBUCIUAKRSV-UHFFFAOYSA-N
in ch i: InChI=1S/C17H14N2O/c20-11-19-16-8-4-1-5-12(16)9-17(19)14-10-18-15-7-3-2-6-13(14)15/h1-8,10-11,17-18H,9H2
comment: AZ1788 is a weak PAR2 antagonist. The structure was optimised to a more potent analogue, <Ligand id=9585/> <Reference id=33052/>.
iupac name: 2,3-dihydro-1'H-[2,3'-biindole]-1-carbaldehyde
approved: f
ligand name: AZ7188
type: SyntheticOrganicLigand

GNF4877
in ch i key: UZIATSFXNVOVFE-OAHLLOKOSA-N
in ch i: InChI=1S/C25H27FN6O4/c1-14(2)36-16-5-6-18(26)17(10-16)19-12-29-23(27)22(30-19)24(33)31-20-11-28-8-7-21(20)32-9-3-4-15(13-32)25(34)35/h5-8,10-12,14-15H,3-4,9,13H2,1-2H3,(H2,27,29)(H,31,33)(H,34,35)/t15-/m1/s1
comment: GNF4877 is a dual DYRK1A/GSK3β inhibitor <Reference id=38844/>. It was designed and reported by the Genomics Institute of the Novartis Research Foundation (GNF) as a strategy to increase β-cell mass and insulin levels, and to improve glycemic control as a novel therapy for type 1 diabetes. Although experiments conducted by the GNF team indicate that DYRK1A inhibition alone is sufficient to promote pancreatic β-cell proliferation, dual inhibition is synergistic. However, GSK3β inhibition may pose a cancer risk <Reference id=38843/>, so selective DYRK1A inhibitors have subsequently been designed (e.g. <Ligand id=10687/>) to ascertain the efficacy of DYRK1A inhibition alone <Reference id=38842/>.
iupac name: (3R)-1-[3-[[3-amino-6-(2-fluoro-5-propan-2-yloxyphenyl)pyrazine-2-carbonyl]amino]pyridin-4-yl]piperidine-3-carboxylic acid
synonym: GNF-4877
approved: f
ligand name: GNF4877
type: SyntheticOrganicLigand

GNF2133
in ch i key: SAZIAQSVBIWIDU-UHFFFAOYSA-N
in ch i: InChI=1S/C24H30N6O2/c1-2-28-9-11-29(12-10-28)24(31)27-23-15-18(3-8-26-23)21-17-30(19-5-13-32-14-6-19)22-16-25-7-4-20(21)22/h3-4,7-8,15-17,19H,2,5-6,9-14H2,1H3,(H,26,27,31)
comment: GNF2133 is a potent, selective and orally bioavailable inhibitor of dual specificity tyrosine phosphorylation regulated kinase 1A (DYRK1A) <Reference id=38842/>. It was designed and reported by the Genomics Institute of the Novartis Research Foundation (GNF). Inhibition of DYRK1A is being examined as a mechanism to promote β-cell proliferation as a novel therapy for type I diabetes. GNF2133 is active in relevant in vivo models. Significantly, GNF2133 is devoid of glycogen synthase kinase-3β (GSK3β) inhibitory activity, which is considered to be a potential long-term treatment liability of pre-exisitng dual DYRK1A/GSK3β inhibitors <Reference id=38843/>. See also <Ligand id=10689/>, which is a selective DYRK1A inhibitor with a different chemical scaffold <Reference id=38848/>.
iupac name: 4-Ethyl-N-(4-(1-(tetrahydro-2H-pyran-4-yl)-1H-pyrrolo[2,3-c]pyridin-3-yl)pyridin-2-yl)piperazine-1-carboxamide
synonym: compound 13g [PMID: 32077280]
synonym: GNF-2133
approved: f
ligand name: GNF2133
type: SyntheticOrganicLigand

compound 5 [Tomassi et al., 2020]
in ch i key: RHCZTJJJLXGIDT-UHFFFAOYSA-N
in ch i: InChI=1S/C24H26N6O2S2/c31-21-17-5-1-3-7-19(17)25-23(27-21)33-15-13-29-9-11-30(12-10-29)14-16-34-24-26-20-8-4-2-6-18(20)22(32)28-24/h1-8H,9-16H2,(H,25,27,31)(H,26,28,32)
comment: Compound 5 is an inhibitor of poly(ADP-ribose) polymerase (PARP) activity, that exhibits some selectivity for tankyrase 2 (TNKS2, PARP5b) <Reference id=38804/>. It is a structural derivative of the PARP1 inhibitor <Ligand id=10671/>.
iupac name: 2-{[2-(4-{2-[(4-oxo-3,4-dihydroquinazolin-2-yl)sulfanyl]ethyl}piperazin-1-yl)ethyl]sulfanyl}-3,4-dihydroquinazolin-4-one
approved: f
ligand name: compound 5 [Tomassi et al., 2020]
type: SyntheticOrganicLigand

icariside II
in ch i key: NGMYNFJANBHLKA-LVKFHIPRSA-N
in ch i: InChI=1S/C27H30O10/c1-12(2)5-10-16-17(28)11-18(29)19-21(31)26(37-27-23(33)22(32)20(30)13(3)35-27)24(36-25(16)19)14-6-8-15(34-4)9-7-14/h5-9,11,13,20,22-23,27-30,32-33H,10H2,1-4H3/t13-,20-,22+,23+,27-/m0/s1
comment: Icariside II (ICS II) is a phosphodiesterase 5 (PDE 5) inhibitor.
iupac name: 5,7-dihydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-enyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxychromen-4-one
synonym: baohuoside I
approved: f
ligand name: icariside II
type: NaturalProductLigand

davalintide
in ch i key: SLYFITHISHUGLZ-QPMCIWSFSA-N
comment: A dual amylin and calcitonin receptor agonist (DACRA).
synonym: DACRA
approved: f
ligand name: davalintide
type: PeptideLigand

compound 8u [PMID: 31999451]
in ch i key: BTNMSAUAXSTYIU-JJKYIXSRSA-N
in ch i: InChI=1S/C27H25N3O5/c1-34-19-13-18(14-20(15-19)35-2)28-27(32)25(12-17-8-4-3-5-9-17)29-24-16-23(30-33)21-10-6-7-11-22(21)26(24)31/h3-11,13-16,25,29,33H,12H2,1-2H3,(H,28,32)/b30-23+
comment: Compound 8u is a novel small molecule that simultaneously inhibits the cancer targets indoleamine-2,3-dioxygenase 1 (IDO1) and signal transducer and activator of transcription 3 (STAT3) <Reference id=38829/> which was designed to elicit multicomponent antitumour immunity. Inhibition of IDO1 acts to circumvent IDO1-induced immunosuppression in the tumour microenvironment and inhbition of STAT3 targets multiple oncogenic signalling pathways in both tumour and immune cells within the tumour microenvironment.
iupac name: (Z)-N-(3,5-Dimethoxyphenyl)-2-((4-(hydroxyimino)-1-oxo-1,4-dihydronaphthalen-2-yl) amino)-3-phenylpropanamide
approved: f
ligand name: compound 8u [PMID: 31999451]
type: SyntheticOrganicLigand

lurbinectedin
in ch i key: YDDMIZRDDREKEP-HWTBNCOESA-N
comment: Lurbinectedin (PM01183) is an investigational anti-tumour agent <Reference id=38826/> with potential activity against a wide range of tumours. Structurally it is a synthetic tetrahydroisoquinoline that is related to the marine ecteinascidins (e.g. <Ligand id=2774/>). Like trabectedin, lurbinectedin binds to the minor groove of DNA. Stable lurbinectedin-DNA adducts induce DNA double- and single-strand breaks which cause cell cycle arrest and ultimately, apoptotic cell death.
synonym: PM01183
synonym: PM 01183
synonym: PM-01183
synonym: Zepzelca®
approved: t
ligand name: lurbinectedin
type: SyntheticOrganicLigand

compound 33 [PMID: 32003991]
in ch i key: ISMDILRWKSYCOD-GNKBHMEESA-N
in ch i: InChI=1S/C28H45N3O5/c1-21(2)26-27(34)29-17-13-8-6-4-3-5-7-9-14-18-36-28(35)30-23(24(32)20-25(33)31-26)19-22-15-11-10-12-16-22/h10-12,15-16,21,23-24,26,32H,3-9,13-14,17-20H2,1-2H3,(H,29,34)(H,30,35)(H,31,33)/t23-,24-,26-/m0/s1
comment: Compound 33 is a biomimetic (of pepstatin A), macrocyclic inhibitor of cathepsin D <Reference id=38822/>. Cathepsin D inhibitors are being examined as novel tools for regulation of this target for application in oncology <Reference id=38823/>. Compound 33 has improved selectivity, solubility and permeability compared to the naturally occurring cathepsin D inhibitor, pepstatin A <Reference id=38824/><Reference id=38822/>.
iupac name: (4S,5S,9S)-4-Benzyl-5-hydroxy-9-isopropyl-1-oxa-3,8,11-triazacyclodocosane-2,7,10-trione
approved: f
ligand name: compound 33 [PMID: 32003991]
type: SyntheticOrganicLigand

motixafortide
in ch i key: JJVZSYKFCOBILL-MKMRYRNGSA-N
comment: Motixafortide (BL8040) is a CXCR4 antagonist that is being developed by Biokine Therapeutics <Reference id=38818/>. It is a 14-residue polypeptide modified from a naturally occurring horseshoe crab protein. Motixafortide acts as an inverse agonist in [35S]GTPγS binding assays <Reference id=38818/>. It induces safe and efficient stem cell mobilisation in MM patients in preparation for autologous stem cell transplantation <Reference id=38820/>, and it is being proposed as a mechanism to improve anti-tumour immune reponse against solid tumours <Reference id=38821/>.
synonym: BL-8040
synonym: BKT140
synonym: 4F-Benzoyl-TN14003
synonym: TF14016
approved: f
ligand name: motixafortide
type: PeptideLigand

hetrombopag
in ch i key: YATJUTCKRWETAB-UHFFFAOYSA-N
in ch i: InChI=1S/C25H22N4O5/c1-14-22(24(31)29(28-14)17-10-9-15-5-2-3-6-16(15)13-17)27-26-19-8-4-7-18(23(19)30)20-11-12-21(34-20)25(32)33/h4,7-13,28,30H,2-3,5-6H2,1H3,(H,32,33)
comment: Hetrombopag is an orally bioavailable, non-peptide small‐molecule thrombopoietin receptor (TPOR/MPL) agonist, that was developed as a treatment for thrombocytopenia <Reference id=38955/>. The parent compound is shown here. It is administered as the ethanolamine/olamine.
iupac name: 5-[2-hydroxy-3-[[5-methyl-3-oxo-2-(5,6,7,8-tetrahydronaphthalen-2-yl)-1H-pyrazol-4-yl]diazenyl]phenyl]furan-2-carboxylic acid
synonym: SHR-8735
synonym: Hengqu®
approved: t
ligand name: hetrombopag
type: SyntheticOrganicLigand

sotorasib
in ch i key: NXQKSXLFSAEQCZ-SFHVURJKSA-N
in ch i: InChI=1S/C30H30F2N6O3/c1-6-23(40)36-12-13-37(18(5)15-36)28-19-14-21(32)26(24-20(31)8-7-9-22(24)39)34-29(19)38(30(41)35-28)27-17(4)10-11-33-25(27)16(2)3/h6-11,14,16,18,39H,1,12-13,15H2,2-5H3/t18-/m0/s1
comment: Sotorasib (AMG510) is a covalent KRASG12C inhibitor <Reference id=38817/> that was developed by Amgen for anti-tumour potential in KRASG12C-driven cancers. It was the first KRAS-targeting drug to be approved for clinical use.
iupac name: 6-fluoro-7-(2-fluoro-6-hydroxyphenyl)-1-(4-methyl-2-propan-2-ylpyridin-3-yl)-4-[(2S)-2-methyl-4-prop-2-enoylpiperazin-1-yl]pyrido[2,3-d]pyrimidin-2-one
synonym: compound (R)-38 [PMID: 31820981]
synonym: AMG 510
synonym: AMG-510
synonym: AMG510
synonym: Lumakras®
synonym: Lumykras®
approved: t
ligand name: sotorasib
type: SyntheticOrganicLigand

compound 25 [PMID: 32023060]
in ch i key: XDVMVEOFPVCHEL-SJKOYZFVSA-N
comment: Compound 25 is a covalent and allosteric KRASG12C inhibitor <Reference id=38815/>. It exhibits favourable pharmacokinetics in preclinical species and produces anti-tumour efficacy in vivo. Compound 25 is claimed in AstraZeneca's patent WO2019110751A1, in which two atropisomers (sterically restrained stereoisomers) with the same chemical formulae are claimed (Example 21 and 22) <Reference id=38816/>.
iupac name: (2R,4aR)-11-Chloro-9-fluoro-10-(2-fluoro-6-hydroxyphenyl)-2,6-dimethyl-3-(prop-2-enoyl)-2,3,4,4a-tetrahydro-1H-pyrazino[1′,2′:4,5]pyrazino[2,3-c]quinolin-5(6H)-one
approved: f
ligand name: compound 25 [PMID: 32023060]
type: SyntheticOrganicLigand

AZ1366
in ch i key: PLGIKHVPQHSSON-UHFFFAOYSA-N
in ch i: InChI=1S/C24H24N4O3/c1-15-12-21(25-10-11-31-2)26-13-20(15)16-6-8-17(9-7-16)23-27-22-18(14-29)4-3-5-19(22)24(30)28-23/h3-9,12-13,29H,10-11,14H2,1-2H3,(H,25,26)(H,27,28,30)
comment: AZ1366 is an orally bioavailable inhibitor of the poly(ADP-ribose) polymerase (PARP) tankyrase enzymes TNKS and TNKS2 <Reference id=38812/>. It exhibits some activity against PARP1 and PARP2. Structurally it is a nicotinamide mimetic that occupies the nicotinamide binding site of the PARP catalytic domain.
iupac name: 8-(hydroxymethyl)-2-[4-[6-(2-methoxyethylamino)-4-methylpyridin-3-yl]phenyl]-3H-quinazolin-4-one
synonym: compound 9 [PMID: 25815142]
synonym: AZ-1366
approved: f
ligand name: AZ1366
type: SyntheticOrganicLigand

mephentermine
canonical SMILES: CNC(Cc1ccccc1)(C)C
isomeric SMILES: CNC(Cc1ccccc1)(C)C
in ch i key: RXQCGGRTAILOIN-UHFFFAOYSA-N
in ch i: InChI=1S/C11H17N/c1-11(2,12-3)9-10-7-5-4-6-8-10/h4-8,12H,9H2,1-3H3
comment: Mephentermine is a cardiac stimulant, but it does not belong to the cardiac glycosides drug family.
iupac name: methyl(2-methyl-1-phenylpropan-2-yl)amine
xref: CHEMBL1201234
synonym: Wyamine Sulfate®
synonym: mephentermine sulfate
synonym: mephentermine sodium
approved: t
ligand name: mephentermine
type: SyntheticOrganicLigand

NVP‐TNKS656
in ch i key: DYGBNAYFDZEYBA-UHFFFAOYSA-N
in ch i: InChI=1S/C27H34N4O5/c1-35-21-6-4-19(5-7-21)26(33)20-8-11-30(12-9-20)16-25(32)31(14-18-2-3-18)15-24-28-23-10-13-36-17-22(23)27(34)29-24/h4-7,18,20H,2-3,8-17H2,1H3,(H,28,29,34)
comment: NVP‐TNKS656 is a potent and selective inhibitor of the poly(ADP-ribose) polymerase (PARP) tankyrase enzymes, that was designed by Novartis for anti-tumour potential <Reference id=38809/>. It is active in vivo.
iupac name: N-(cyclopropylmethyl)-2-[4-(4-methoxybenzoyl)piperidin-1-yl]-N-[(4-oxo-3,5,7,8-tetrahydropyrano[4,3-d]pyrimidin-2-yl)methyl]acetamide
xref: CHEMBL2419706
synonym: NVP-TNKS-656
synonym: TNKS656
synonym: TNK-S656
synonym: TNK S656
synonym: NVPTNKS656
synonym: compound 43 [PMID: 23844574]
synonym: example 5 [WO2013012723A1]
approved: f
ligand name: NVP‐TNKS656
type: SyntheticOrganicLigand

RK-287107
in ch i key: FZQYCOUBRJEYBC-UHFFFAOYSA-N
in ch i: InChI=1S/C22H26F2N4O2/c23-14-11-16(24)19-18(12-14)28(9-10-29)13-22(19)5-7-27(8-6-22)21-25-17-4-2-1-3-15(17)20(30)26-21/h11-12,29H,1-10,13H2,(H,25,26,30)
comment: RK-287107 is an orally bioavilable, non-selective tankyrase inhibitor <Reference id=38808/>. It blocks growth of β-catenin-dependent colorectal cancer xenograft tumours in preclinical models.
iupac name: 2-[4,6-difluoro-1-(2-hydroxyethyl)spiro[2H-indole-3,4'-piperidine]-1'-yl]-5,6,7,8-tetrahydro-3H-quinazolin-4-one
synonym: RK287107
approved: f
ligand name: RK-287107
type: SyntheticOrganicLigand

compound 2e [PMID: 31900320]
canonical SMILES: CCOc1nc2c(s1)c(Cl)c(cc2)Oc1ccc(cn1)/C=C/[C@@H](NC(=O)C)C
isomeric SMILES: CCOc1nc2c(s1)c(Cl)c(cc2)Oc1ccc(cn1)/C=C/[C@@H](NC(=O)C)C
in ch i key: CYSWUSAYJNCAKA-FYJFLYSWSA-N
comment: Acetyl CoA carboxylase 2 (ACC2) inhibitor that demonstrates significant antidiabetic effects through inhibition of ACC2-dependent pathways.
iupac name: N-[(2S,3E)-4-{6-[(7-chloro-2-ethoxy-1,3-benzothiazol-6-yl)oxy]pyridin-3-yl}but-3-en-2-yl]acetamide
approved: f
ligand name: compound 2e [PMID: 31900320]
type: SyntheticOrganicLigand

A-908292
canonical SMILES: COC(=O)N[C@H](C#Cc1cnc(s1)Oc1ccc(cc1)OC(C)C)C
isomeric SMILES: COC(=O)N[C@H](C#Cc1cnc(s1)Oc1ccc(cc1)OC(C)C)C
in ch i key: OLMPAYQFDVALIH-ZDUSSCGKSA-N
in ch i: InChI=1S/C18H20N2O4S/c1-12(2)23-14-6-8-15(9-7-14)24-18-19-11-16(25-18)10-5-13(3)20-17(21)22-4/h6-9,11-13H,1-4H3,(H,20,21)/t13-/m0/s1
comment: Acetyl CoA carboxylase 2 (ACC2) inhibitor, resulting in a reduction of serum glucose and triglyceride levels.
iupac name: methyl N-[(2S)-4-[2-(4-propan-2-yloxyphenoxy)-1,3-thiazol-5-yl]but-3-yn-2-yl]carbamate
approved: f
ligand name: A-908292
type: SyntheticOrganicLigand

HWL-088
in ch i key: NJYJBYPNDWNZAH-UHFFFAOYSA-N
in ch i: InChI=1S/C22H19FO4/c1-15-5-2-3-8-19(15)17-7-4-6-16(11-17)13-26-18-9-10-21(20(23)12-18)27-14-22(24)25/h2-12H,13-14H2,1H3,(H,24,25)
comment: HWL-088 is a highly potent free fatty acid receptor 1 (FFA1/GPR40) agonist bearing a phenoxyacetic acid scaffold. HWL-088 significantly improves glucose tolerance in normal and diabetic models.
iupac name: 2-[2-fluoro-4-[[3-(2-methylphenyl)phenyl]methoxy]phenoxy]acetic acid
synonym: HWL088
synonym: HWL 088
synonym: HY-130120
synonym: CS-0105155
approved: f
ligand name: HWL-088
type: SyntheticOrganicLigand

UCSF4226
canonical SMILES: COc1ccc(c(c1)CNc1cccnc1)Br
isomeric SMILES: COc1ccc(c(c1)CNc1cccnc1)Br
in ch i key: BLNNXJOEJRKHAM-UHFFFAOYSA-N
in ch i: InChI=1S/C13H13BrN2O/c1-17-12-4-5-13(14)10(7-12)8-16-11-3-2-6-15-9-11/h2-7,9,16H,8H2,1H3
comment: UCSF4226 was found to act as selective agonist of the melatonin receptor 1B (MT2 receptor) <Reference id=38751/>. It represents a novel chemotype for MT ligands, and was designed using structure-based optimisation of a lead molecule that was identified in a docking screen of 150 million virtual molecules against a MT1 crystal structure.
iupac name: N-[(2-bromo-5-methoxyphenyl)methyl]pyridin-3-amine
synonym: ZINC000128734226
synonym: Z1610979660
approved: f
ligand name: UCSF4226
type: SyntheticOrganicLigand

UCSF7447
canonical SMILES: Clc1ccc(c(c1)Br)CNc1cccc(c1)c1nnc[nH]1
isomeric SMILES: Clc1ccc(c(c1)Br)CNc1cccc(c1)c1nnc[nH]1
in ch i key: QPTCYEYTAWEZNT-UHFFFAOYSA-N
in ch i: InChI=1S/C15H12BrClN4/c16-14-7-12(17)5-4-11(14)8-18-13-3-1-2-10(6-13)15-19-9-20-21-15/h1-7,9,18H,8H2,(H,19,20,21)
comment: UCSF7447 was found to act as selective inverse agonist of the melatonin receptor 1A (MT1 receptor) <Reference id=38751/>. It represents a novel chemotype for MT ligands, and was designed using structure-based optimisation of a lead molecule that was identified in a docking screen of 150 million virtual molecules against a MT1 crystal structure.
iupac name: N-[(2-bromo-4-chlorophenyl)methyl]-3-(1H-1,2,4-triazol-5-yl)aniline
synonym: ZINC000555417447
synonym: Z1514261971
approved: f
ligand name: UCSF7447
type: SyntheticOrganicLigand

UCSF3384
canonical SMILES: CC(c1ccc(cc1)CNc1cccc(c1)c1[nH]cnn1)C
isomeric SMILES: CC(c1ccc(cc1)CNc1cccc(c1)c1[nH]cnn1)C
in ch i key: GXZIJEFRHJOZBW-UHFFFAOYSA-N
in ch i: InChI=1S/C18H20N4/c1-13(2)15-8-6-14(7-9-15)11-19-17-5-3-4-16(10-17)18-20-12-21-22-18/h3-10,12-13,19H,11H2,1-2H3,(H,20,21,22)
comment: UCSF3384 was found to act as selective inverse agonist of the melatonin receptor 1A (MT1 receptor) <Reference id=38751/>. It represents a novel chemotype for MT ligands, and was designed using structure-based optimisation of a lead molecule that was identified in a docking screen of 150 million virtual molecules against a MT1 crystal structure.
iupac name: N-[(4-propan-2-ylphenyl)methyl]-3-(1H-1,2,4-triazol-5-yl)aniline
synonym: ZINC000157673384
synonym: Z1480758218
approved: f
ligand name: UCSF3384
type: SyntheticOrganicLigand

compound 12 [PMID: 31990537]
in ch i key: LXSODRTWQNWTOG-UHFFFAOYSA-N
in ch i: InChI=1S/C17H13N5O4S2/c18-28(24,25)19-9-14-21-22-16(26-14)15(23)17-20-12-7-6-11(8-13(12)27-17)10-4-2-1-3-5-10/h1-8,19H,9H2,(H2,18,24,25)
comment: Compound 12 is reported as a reversible inhibitor of endothelial lipase <Reference id=38761/>. It is active in vivo, elevating plasma HDL-cholesterol levels in a mouse pharmacodynamics model. The chemical structure is claimed in Bristol-Myers Squibb's patent WO2014042939A1 <Reference id=38762/>. Compound 12 is a tool compound that is suitable to help establish proof-of-concept for pharmacological inhibition of EL as a alternative mechanism to raise HDL-cholesterol levels as a route to clinical cardiovascular benefit.
iupac name: 2-(6-phenyl-1,3-benzothiazole-2-carbonyl)-5-[(sulfamoylamino)methyl]-1,3,4-oxadiazole
synonym: example 24 [WO2014042939A1]
approved: f
ligand name: compound 12 [PMID: 31990537]
type: SyntheticOrganicLigand

vorasidenib
in ch i key: QCZAWDGAVJMPTA-RNFRBKRXSA-N
in ch i: InChI=1S/C14H13ClF6N6/c1-6(13(16,17)18)22-11-25-10(8-4-3-5-9(15)24-8)26-12(27-11)23-7(2)14(19,20)21/h3-7H,1-2H3,(H2,22,23,25,26,27)/t6-,7-/m1/s1
comment: Vorasidenib (AG-881) inhibits mutant forms of the isocitrate dehydrogenases (IDH1 and IDH2) <Reference id=38752/> that catalyse the generation of the oncogenic metabolite d-2-hydroxyglutarate (2-HG). This compound and others, and their use for treating cancer are claimed in patent US10028961 <Reference id=38756/>. Vorasidenib can cross the blood brain barrier, and is being proposed as a chemotherapeutic for IDH mutation +ve cancers including gliomas <Reference id=38754/> and hematological malignancies <Reference id=38755/>. X-ray cocrystal structures of vorasidenib with mutant IDH1 and mutant IDH2 have been deposited with the RCSB Protein Data Bank <Reference id=38753/><Reference id=38752/>. The X-ray structures show that vorasidenib binds at an allosteric pocket formed in IDH homodimers, at the interface of the two monomers.
iupac name: 6-(6-chloropyridin-2-yl)-2-N,4-N-bis[(2R)-1,1,1-trifluoropropan-2-yl]-1,3,5-triazine-2,4-diamine
synonym: AG-881
synonym: AG881
approved: f
ligand name: vorasidenib
type: SyntheticOrganicLigand

BMS-986260
canonical SMILES: OCCn1cnc(c1c1ccc2n(n1)c(C#N)cn2)c1ccc(c(c1)Cl)F
isomeric SMILES: OCCn1cnc(c1c1ccc2n(n1)c(C#N)cn2)c1ccc(c(c1)Cl)F
in ch i key: VZZBCNXVZFAIQX-UHFFFAOYSA-N
in ch i: InChI=1S/C18H12ClFN6O/c19-13-7-11(1-2-14(13)20)17-18(25(5-6-27)10-23-17)15-3-4-16-22-9-12(8-21)26(16)24-15/h1-4,7,9-10,27H,5-6H2
comment: BMS-986260 is a potent, selective and orally bioavailable TGFβR1 inhibitor, that was developed for immuno-oncology potential <Reference id=38750/>. The chemical structure of BMS-986260 is one of those claimed in patent WO2016140884A1 (Rigel Pharmaceuticals/Bristol-Myers Squibb). The PubChem CID match was obtained using the SMILES for BMS-986260 that was generated from the structure image presented in <Reference id=38750/>.
iupac name: 6-[5-(3-chloro-4-fluorophenyl)-3-(2-hydroxyethyl)imidazol-4-yl]imidazo[1,2-b]pyridazine-3-carbonitrile
synonym: BMS986260
synonym: Example 32' [WO2016140884A1]
synonym: compound 10 [Velaparthi et al., 2020]
approved: f
ligand name: BMS-986260
type: SyntheticOrganicLigand

JNJ-42226314
in ch i key: IVOACCSOISMVBL-UHFFFAOYSA-N
in ch i: InChI=1S/C26H24FN5O2S/c27-20-2-4-21(5-3-20)32-9-7-18-15-19(1-6-23(18)32)25(33)31-16-22(17-31)29-10-12-30(13-11-29)26(34)24-28-8-14-35-24/h1-9,14-15,22H,10-13,16-17H2
comment: A potent, selective and reversible non-covalent monoacylglycerol lipase (MAGL) inhibitor that demonstrates dose-dependent enhancement of the major endocannabinoid 2-arachidonoylglycerol as well as efficacy in models of neuropathic and inflammatory pain.
iupac name: [1-(4-fluorophenyl)indol-5-yl]-[3-[4-(1,3-thiazole-2-carbonyl)piperazin-1-yl]azetidin-1-yl]methanone
synonym: JNJ 42226314
synonym: JNJ42226314
approved: f
ligand name: JNJ-42226314
type: SyntheticOrganicLigand

pethidine
canonical SMILES: CCOC(=O)C1(CCN(CC1)C)c1ccccc1
isomeric SMILES: CCOC(=O)C1(CCN(CC1)C)c1ccccc1
in ch i key: XADCESSVHJOZHK-UHFFFAOYSA-N
in ch i: InChI=1S/C15H21NO2/c1-3-18-14(17)15(9-11-16(2)12-10-15)13-7-5-4-6-8-13/h4-8H,3,9-12H2,1-2H3
comment: Meperidine is an opioid analgesic.
iupac name: ethyl 1-methyl-4-phenylpiperidine-4-carboxylate
xref: CHEMBL607
synonym: meperidine
synonym: Algil
synonym: Lidol
synonym: Alodan
synonym: Dolsin
synonym: Dolosal
synonym: Mialgin
synonym: Dispadol
synonym: Dolantin
synonym: Mefedina
synonym: Pethanol
synonym: Dolestine
synonym: Piridosal
synonym: Centralgin
synonym: Spasmodlin
synonym: Isonipecaine
synonym: Petidin Dolargan
synonym: Meperidine Hydrochloride
synonym: Demerol®
approved: t
ligand name: pethidine
type: SyntheticOrganicLigand

nidufexor
in ch i key: JYTIXGYXBIBOMN-UHFFFAOYSA-N
in ch i: InChI=1S/C27H22ClN3O4/c1-30-25-21-13-20(28)11-12-23(21)35-16-22(25)24(29-30)26(32)31(14-17-5-3-2-4-6-17)15-18-7-9-19(10-8-18)27(33)34/h2-13H,14-16H2,1H3,(H,33,34)
comment: Nidufexor (LMB763) is an orally bioavailable non-bile acid agonist of the ligand-activated nuclear farnesoid X receptor (FXR) that is being developed by Novartis for the treatment of nonalcoholic steatohepatitis (NASH) <Reference id=38730/>. FXR agonists reduce steatosis, hepatocellular inflammation, hepatic injury and fibrosis.
iupac name: 4-[[benzyl-(8-chloro-1-methyl-4H-chromeno[4,3-c]pyrazole-3-carbonyl)amino]methyl]benzoic acid
synonym: LMB763
synonym: LMB-763
synonym: compound 1 [PMID: 31940200]
approved: f
ligand name: nidufexor
type: SyntheticOrganicLigand

licogliflozin
in ch i key: XFJAMQQAAMJFGB-ZQGJOIPISA-N
in ch i: InChI=1S/C23H28O7/c1-2-14-4-5-15(23-22(27)21(26)20(25)19(12-24)30-23)11-16(14)9-13-3-6-17-18(10-13)29-8-7-28-17/h3-6,10-11,19-27H,2,7-9,12H2,1H3/t19-,20-,21+,22-,23+/m1/s1
comment: Licogliflozin (LIK-066) is an orally bioactive inhibitor of sodium/glucose cotransporters 1 and 2 (SGLT1, SGLT2). It was developed by Novartis for the treatment of obesity, non-alcoholic steatohepatitis, and type 2 diabetes, but the program was discontinued in 2018 <Reference id=38728/>.
iupac name: (2S,3R,4R,5S,6R)-2-[3-(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)-4-ethylphenyl]-6-(hydroxymethyl)oxane-3,4,5-triol
synonym: LIK-066
synonym: LIK066
synonym: example 62 [WO2011048112A1]
approved: f
ligand name: licogliflozin
type: SyntheticOrganicLigand

lazucirnon
in ch i key: DWKNOLCXIFYNFV-HSZRJFAPSA-N
in ch i: InChI=1S/C27H34ClN5O3/c1-17-13-19(5-6-22(17)28)16-32-11-9-21(10-12-32)33-23(7-8-25(33)34)26(35)30-24-15-20(14-18(2)29-24)27(36)31(3)4/h5-6,13-15,21,23H,7-12,16H2,1-4H3,(H,29,30,35)/t23-/m1/s1
comment: Lazucirnon (AKST4290, formerly known as ALK4290) is a CCR3 antagonist that was developed by Alkahest as a novel oral therapy for wet age-related macular degeneration (AMD). It acts as a modulator of pathologic inflammation by inhibiting the CCR3/eotaxin axis and subsequent eosinophil accumulation. ALK4290 is now being repurposed for Parkinson's disease. The structure that is presented here was obtained from the NIH ChemIDplus chemical information resource, where it is listed as ALK4290. The structure matches example 11 that is claimed in patent WO2012045803A1 which was granted to Boehringer Ingelheim <Reference id=38726/>.
iupac name: 2-[[(2R)-1-[1-[(4-chloro-3-methylphenyl)methyl]piperidin-4-yl]-5-oxopyrrolidine-2-carbonyl]amino]-N,N,6-trimethylpyridine-4-carboxamide
xref: CHEMBL3670800
synonym: ALK4290
synonym: ALK-4290
synonym: Example 11 [WO2012045803A1]
synonym: AKST-4290
synonym: AKST4290
approved: f
ligand name: lazucirnon
type: SyntheticOrganicLigand

BD-1047
canonical SMILES: CN(CCc1ccc(c(c1)Cl)Cl)CCN(C)C
isomeric SMILES: CN(CCc1ccc(c(c1)Cl)Cl)CCN(C)C
in ch i key: MGVRNMUKTZOQOW-UHFFFAOYSA-N
in ch i: InChI=1S/C13H20Cl2N2/c1-16(2)8-9-17(3)7-6-11-4-5-12(14)13(15)10-11/h4-5,10H,6-9H2,1-3H3
iupac name: N-[2-(3,4-dichlorophenyl)ethyl]-N,N',N'-trimethylethane-1,2-diamine
xref: CHEMBL143360
synonym: BD 1047
synonym: BD1047
approved: f
ligand name: BD-1047
type: SyntheticOrganicLigand

oxycodegol
in ch i key: RQHILGKAOIGUHU-XPLSERNMSA-N
in ch i: InChI=1S/C31H49NO10/c1-32-9-8-30-27-23-4-5-24(35-3)28(27)42-29(30)25(6-7-31(30,33)26(32)22-23)41-21-20-40-19-18-39-17-16-38-15-14-37-13-12-36-11-10-34-2/h4-5,25-26,29,33H,6-22H2,1-3H3/t25-,26+,29-,30-,31+/m0/s1
comment: Oxycodegol (NKTR-181; Nektar Therapeutics) is a μ-opioid receptor agonist analgesic <Reference id=38719/>. It was designed to enter the brain slowly, so as to reduce CNS-mediated side effects and abuse potential.
synonym: loxicodegol (deleted INN)
synonym: NKTR-181
synonym: NKTR181
approved: f
ligand name: oxycodegol
type: SyntheticOrganicLigand

samidorphan
in ch i key: RYIDHLJADOKWFM-MAODMQOUSA-N
in ch i: InChI=1S/C21H26N2O4/c22-19(26)15-4-3-13-9-16-21(27)6-5-14(24)10-20(21,17(13)18(15)25)7-8-23(16)11-12-1-2-12/h3-4,12,16,25,27H,1-2,5-11H2,(H2,22,26)/t16-,20-,21-/m1/s1
comment: Samidorphan (ALKS-33) is a novel μ-opioid receptor antagonist that was developed by Alkermes <Reference id=38716/>. Structurally it is a <Ligand id=1639/> analogue. The intention was for samidorphan to be used in combination with the atypical antipsychotic <Ligand id=47/> (in a formulation known as Lybalvi®, ALKS-3831, or the abbreviation OLZ/SAM) as a therapy for schizophrenia and bipolar disorder. Addition of samidorphan was proposed to mitigate olanzapine-induced weight gain.
iupac name: (1R,9R,10S)-17-(cyclopropylmethyl)-3,10-dihydroxy-13-oxo-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,5-triene-4-carboxamide
xref: CHEMBL426084
synonym: ALKS33
synonym: ALKS-33
synonym: compound 5 [PMID:15808478]
synonym: Lybalvi® (olanzapine + samidorphan)
approved: t
ligand name: samidorphan
type: SyntheticOrganicLigand

compound 16 [PMID: 31977207]
in ch i key: ZNXWRMSQZDHKCM-SBRQVZBJSA-N
in ch i: InChI=1S/C38H56N2O11/c1-37-15-7-9-23(11-13-25-27(21-39(3)4)35(43)48-29(25)31(37)50-37)33(41)46-19-17-45-18-20-47-34(42)24-10-8-16-38(2)32(51-38)30-26(14-12-24)28(22-40(5)6)36(44)49-30/h9-10,25-32H,7-8,11-22H2,1-6H3/b23-9+,24-10+/t25-,26-,27-,28?,29-,30-,31-,32-,37+,38+/m0/s1
comment: Compound 16 (acidified with fumaric acid) is reported as an activator of pyruvate kinase M2 (PKM2) that has in vivo anti-tumour activity against glioblastoma multiforme xenografts <Reference id=38709/>. It is a prodrug, with the active form being compound 5 in the discovery article.
approved: f
ligand name: compound 16 [PMID: 31977207]
type: SyntheticOrganicLigand

compound 7 [PMID: 31955578]
in ch i key: ZJXHODMMACVLQQ-NEPJUHHUSA-N
in ch i: InChI=1S/C18H23N7O2S/c1-11-9-26-7-5-24(11)15-14-17(28-16(20-14)13-3-4-19-23-13)22-18(21-15)25-6-8-27-10-12(25)2/h3-4,11-12H,5-10H2,1-2H3,(H,19,23)/t11-,12+/m1/s1
comment: Compound 7 was designed by scientists at Novartis, as a potent and selective brain-penetrant inhibitor of mechanistic target of rapamycin (mTOR) <Reference id=38705/>. It is an ATP-competitive inhibitor. It is already established that inhibition of mTOR in the CNS providees clinical efficacy in certain seizure disorders (such as tuberous sclerosis complex; TSC <Reference id=38706/>) that are associated with overactivated mTOR signalling <Reference id=38707/><Reference id=38708/>. The allosteric mTOR inhibitor <Ligand id=5889/> is already approved as adjunctive treatment for patients with TSC-associated partial-onset seizures. Compound 7 was optimised to provide a molecule with improved brain permeability compared to everolimus.
iupac name: (S)-3-Methyl-4-(7-((R)-3-methylmorpholino)-2-(1H-pyrazol-3-yl)thiazolo[5,4-d]pyrimidin-5-yl)morpholine
approved: f
ligand name: compound 7 [PMID: 31955578]
type: SyntheticOrganicLigand

efsevin
in ch i key: QMRVCOQYPZTTAJ-UHFFFAOYSA-N
in ch i: InChI=1S/C20H21NO4S/c1-3-25-20(22)18-13-14-21(19(18)16-7-5-4-6-8-16)26(23,24)17-11-9-15(2)10-12-17/h4-13,19H,3,14H2,1-2H3
comment: Synthetic agonist of the voltage-dependent anion channel 2 (VDAC2, link to the HGNC VDAC family).
iupac name: ethyl 1-(4-methylphenyl)sulfonyl-2-phenyl-2,5-dihydropyrrole-3-carboxylate
approved: f
ligand name: efsevin
type: SyntheticOrganicLigand

rodatristat
in ch i key: ZNSPHKJFQDEABI-NZQKXSOJSA-N
comment: Rodatristat (KAR5417) inhibits both isoforms of L-Tryptophan hydroxylase (TPH) <Reference id=38702/>. The TPH enzymes are responsible for biosynthesis of 5-HT. TPH1 is expressed by intestinal enterochromaffin cells where most peripheral 5-HT is formed, and THP2 is exclusively expressed in the CNS and generates 5-HT in the brain. Rodatristat acts as a serotonin synthesis inhibitor. As rodatristat cannot cross the blood-brain-barrier its activity is restricted to inhibition of peripherally expressed TPH1 and it should not produce the undesirable psychiatric side-effects that are known to result from any reduction in central 5-HT level. Inhibition of serotonin synthesis is being actively pursued as a mechanistic approach for application to the treatment of the expansive range of diseases that have been associated with a dysfunctional peripheral serotonin system (carcinoid syndrome, gastro-intestinal diseases, fibrotic diseases, NAFLD, atherothrombotic diseases, pulmonary arterial hypertension and some cancers and immune diseases <Reference id=38703/><Reference id=38704/>).
iupac name: (3S)-8-[2-amino-6-[(1R)-1-(4-chloro-2-phenylphenyl)-2,2,2-trifluoroethoxy]pyrimidin-4-yl]-2,8-diazaspiro[4.5]decane-3-carboxylic acid
xref: CHEMBL4104957
synonym: compound 15a [PMID: 28041831]
synonym: KAR5417
synonym: KAR-5417
approved: f
ligand name: rodatristat
type: SyntheticOrganicLigand

rodatristat ethyl
in ch i key: TZSZZENYCISATO-WIOPSUGQSA-N
comment: Rodatristat ethyl (KAR5585) is the inactive prodrug of rodatristat <Reference id=38702/>. It is bioconverted in vivo by esterase activity.
iupac name: ethyl (3S)-8-[2-amino-6-[(1R)-1-(4-chloro-2-phenylphenyl)-2,2,2-trifluoroethoxy]pyrimidin-4-yl]-2,8-diazaspiro[4.5]decane-3-carboxylate
xref: CHEMBL4069704
synonym: KAR-5585
synonym: KAR5585
synonym: compound 15b [PMID: 28041831]
synonym: RVT-1201
approved: f
ligand name: rodatristat ethyl
type: SyntheticOrganicLigand

cilofexor
in ch i key: KZSKGLFYQAYZCO-UHFFFAOYSA-N
comment: Cilofexor (GS-9674) is a nonsteroidal farnesoid X receptor (FXR) agonist. It was originally identified by Phenex Pharmaceuticals <Reference id=38674/> and is being developed by Gilead Pharmaceuticals for hepatic anti-steatotic activity, and potential to treat nonalcoholic fatty liver disease (NAFLD) and/or nonalcoholic steatohepatitis (NASH). Successful treatment of these liver conditions will most likely be achieved using combinations of antilipemic, anti-inflammatory and anti-fibrotic agents.
iupac name: 2-[3-[2-chloro-4-[[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]methoxy]phenyl]-3-hydroxyazetidin-1-yl]pyridine-4-carboxylic acid
synonym: GS-9674
synonym: GS9674
synonym: example 13/9 [US10485795B2]
approved: f
ligand name: cilofexor
type: SyntheticOrganicLigand

RO0094889
in ch i key: NELWQUQCCZMRPB-UBPLGANQSA-N
in ch i: InChI=1S/C15H19N3O6/c1-5-10-6-18(15(21)17-13(10)16)14-12(24-9(4)20)11(7(2)22-14)23-8(3)19/h5-7,11-12,14H,1H2,2-4H3,(H2,16,17,21)/t7-,11-,12-,14-/m1/s1
comment: RO0094889 is a prodrug dihydropyrimidine dehydrogenase (DPD) inhibitor that was developed by Hoffmann-La Roche <Reference id=38360/>. RO0094889 is metabolised by enzymes secreted by tumours to produce the DPD inhibitor 5-vinyluracil. This leads to inhibition of DPD-mediated catabolic degradation of the <Ligand id=4789/> produced locally in tumours from <Ligand id=6799/> <Reference id=38361/>. RO0094889 is orally active.
iupac name: [(2R,3R,4R,5R)-4-acetyloxy-5-(4-amino-5-ethenyl-2-oxopyrimidin-1-yl)-2-methyloxolan-3-yl] acetate
synonym: compound 11c [PMID: 2617910]
synonym: Ro 09-4889
approved: f
ligand name: RO0094889
type: SyntheticOrganicLigand

dapansutrile
canonical SMILES: N#CCCS(=O)(=O)C
isomeric SMILES: N#CCCS(=O)(=O)C
in ch i key: LQFRYKBDZNPJSW-UHFFFAOYSA-N
in ch i: InChI=1S/C4H7NO2S/c1-8(6,7)4-2-3-5/h2,4H2,1H3
comment: Dapansutrile (OLT1177) acts as a NLRP3 inflammasome inhibitor. It is a clinical candidate that is being developed by Olatec Therapeutics. Inhibition of the NLRP3 inflammasome reduces maturation of the pro-inflammatory, disease-associated cytokines IL-1β and IL-18 <Reference id=36018/>. Immunoprecipitation and FRET analysis indicates that OLT1177 inhibits inflammasome oligomerization by blocking NLRP3-ASC, and NLRP3-caspase-1 interaction, but may also directly target NLRP3 (as assessed by inhibition of recombinant NLRP3 ATPase activity by dapansutrile) <Reference id=36018/>. SARS-CoV-2 and COVID-19: Dapansutrile's anti-inflammatory potential (via oral administration) is being investigated in COVID-19 patients with moderate symptoms.
iupac name: 3-methylsulfonylpropanenitrile
xref: CHEMBL3989943
synonym: OLT1177
synonym: OLT-1177
approved: f
ligand name: dapansutrile
type: SyntheticOrganicLigand

compound 25 [Zhang et al., 2020]
in ch i key: IBIKHMZPHNKTHM-RDTXWAMCSA-N
comment: Compound 25 is an allosteric inhibitor of RORγt <Reference id=38667/>. Its pharmacokinetic profile makes it suitable for oral administration. The chemical structure and its use are claimed in Merck's patent WO2014028600A2 <Reference id=38668/>.
iupac name: (3S,4R)-1-[1-(2-chloro-6-cyclopropylbenzoyl)-4-fluoro-1H-indazol-3-yl]-3-hydroxypiperidine-4-carboxylic acid
synonym: example 6B [WO2014028600A2]
approved: f
ligand name: compound 25 [Zhang et al., 2020]
type: SyntheticOrganicLigand

MRL-871
in ch i key: DANLZOIRUUHIIX-UHFFFAOYSA-N
comment: MRL-871 is a negative allosteric modulator of the nuclear hormone receptor RORγt <Reference id=38664/><Reference id=38663/>. It binds to a site in the receptor's ligand binding domain that is distal to the canonical ortherosteric binding site.
iupac name: 4-[1-[2-chloro-6-(trifluoromethyl)benzoyl]indazol-3-yl]benzoic acid
xref: CHEMBL3598140
synonym: MRL871
approved: f
ligand name: MRL-871
type: SyntheticOrganicLigand

SLM6071469
in ch i key: QOYVZPSXPWIXAV-INIZCTEOSA-N
in ch i: InChI=1S/C22H19F6N5O2/c23-21(24,25)14-6-3-12(4-7-14)11-34-17-8-5-13(10-15(17)22(26,27)28)18-31-19(35-32-18)16-2-1-9-33(16)20(29)30/h3-8,10,16H,1-2,9,11H2,(H3,29,30)/t16-/m0/s1
comment: Compound 10 is an inhibitor of sphingosine kinase 2 <Reference id=38660/>. This compound exploits a novel side cavity on the kinase to provide enhanced potency and selectivity. The PubChem entry for this compound originated via SureChEMBL patent extraction, and is derived from patent WO2017172989A1 from researchers at Virginia Tech <Reference id=38661/>.
iupac name: (2S)-2-[3-[3-(trifluoromethyl)-4-[[4-(trifluoromethyl)phenyl]methoxy]phenyl]-1,2,4-oxadiazol-5-yl]pyrrolidine-1-carboximidamide
synonym: compound 10 [PMID: 31895563]
approved: f
ligand name: SLM6071469
type: SyntheticOrganicLigand

compound 21b [PMID: 31944697]
in ch i key: XZENCCSBEQTERZ-UHFFFAOYSA-N
in ch i: InChI=1S/C17H13ClN2O4/c18-14-7-5-13(6-8-14)12-3-1-11(2-4-12)10-23-16-9-15(24-20-16)17(21)19-22/h1-9,22H,10H2,(H,19,21)
comment: Compound 21b is reported as a selective inhibitor of acid sphingomyelinase (ASM; SMPD1) <Reference id=38659/>. It crosses the blood-brain-barrier in a rat model and has predicted value as an antidepressant based on outcomes from in vivo behavioural models of depression.
iupac name: 3-((4'-Chloro-[1,1'-biphenyl]-4-yl)methoxy)-N-hydroxyisoxazole-5-carboxamide
approved: f
ligand name: compound 21b [PMID: 31944697]
type: SyntheticOrganicLigand

WJYK50
canonical SMILES: CCCCCCCCCCOc1cc(ccc1OC)C(=O)NO
isomeric SMILES: CCCCCCCCCCOc1cc(ccc1OC)C(=O)NO
in ch i key: QKPYTKNEFFAFOV-UHFFFAOYSA-N
in ch i: InChI=1S/C18H29NO4/c1-3-4-5-6-7-8-9-10-13-23-17-14-15(18(20)19-21)11-12-16(17)22-2/h11-12,14,21H,3-10,13H2,1-2H3,(H,19,20)
comment: WJYK50 is an inhibitor of acid sphingomyelinase (ASM; SMPD1) <Reference id=38658/>. It produces anti-apoptosis and anti-inflammatory effects in vitro.
iupac name: 3-(Decyloxy)-N-hydroxy-4-methoxybenzamide
synonym: compound 1c [PMID: 29649738]
approved: f
ligand name: WJYK50
type: SyntheticOrganicLigand

ifidancitinib
in ch i key: OYFMQDVLFYKOPZ-UHFFFAOYSA-N
in ch i: InChI=1S/C20H18FN5O3/c1-10-6-13(8-16(28-3)17(10)21)24-19-22-9-11(2)18(26-19)23-12-4-5-15-14(7-12)25-20(27)29-15/h4-9H,1-3H3,(H,25,27)(H2,22,23,24,26)
comment: The chemical structure that was submitted to the WHO for the INN ifidancitinib matches structures that are claimed as Janus kinase (JAK) inhibitors in Rigel Pharmaceuticals' patent WO2012015972A1 <Reference id=38646/>. Structurally ifidancitinib is identical to <Ligand id=10637/> (fosifidancitinib) but without the phosphate group. The closest structural match in the patent is example I-221 but this has deuterium iotopes replacing some of the hydrogens on methylanilino group. Rigel declare two JAK inhibitor programmes on their pipeline webpage; one in partnership with Aclaris Therapeutics (ATI-501/ATI-502, oral and topical formulations respectively) for dermatological applications, and the second in partnership with AstraZeneca through which AZD0449 (R256) is being investigated as an inhalation asthma therapeutic. None of these investigational agents have published name to structure declarations, so at the moment we cannot definitively ascribe a research code to this chemical structure.
iupac name: 5-[[2-(4-fluoro-3-methoxy-5-methylanilino)-5-methylpyrimidin-4-yl]amino]-3H-1,3-benzoxazol-2-one
approved: f
ligand name: ifidancitinib
type: SyntheticOrganicLigand

fosifidancitinib
in ch i key: JTUBTEKGIDQZMZ-UHFFFAOYSA-N
in ch i: InChI=1S/C21H21FN5O7P/c1-11-6-14(8-17(32-3)18(11)22)25-20-23-9-12(2)19(26-20)24-13-4-5-16-15(7-13)27(21(28)34-16)10-33-35(29,30)31/h4-9H,10H2,1-3H3,(H2,29,30,31)(H2,23,24,25,26)
comment: Fosifidancitinib is a Janus kinase (JAK) inhibitor that is claimed in Rigel Pharmaceuticals' patent WO2010085684A1 <Reference id=38645/>. Strictly I-538 refers to the sodium salt but we represent the parent molecule in this entry. The chemical structure that was submitted to the WHO for the INN fosifidancitinib matches the structure of example I-538 (minus the sodium). Rigel declare two JAK inhibitor programmes on their pipeline webpage; one in partnership with Aclaris Therapeutics (ATI-501/ATI-502, oral and topical formulations respectively) for dermatological applications, and the second in partnership with AstraZeneca through which AZD0449 (R256) is being investigated as an inhalation asthma therapeutic. None of these investigational agents have published name to structure declarations.
iupac name: [5-[[2-(4-fluoro-3-methoxy-5-methylanilino)-5-methylpyrimidin-4-yl]amino]-2-oxo-1,3-benzoxazol-3-yl]methyl dihydrogen phosphate
approved: f
ligand name: fosifidancitinib
type: SyntheticOrganicLigand

PROTAC 3
in ch i key: NICKHWYZMNLEPJ-TZSMONEZSA-N
comment: This compound is a gefitinib-based VHL-recruiting EGFR degrader (PROTAC; proteolysis targeting chimera) <Reference id=38643/>.
synonym: Gefitinib-based PROTAC 3
approved: f
ligand name: PROTAC 3
type: SyntheticOrganicLigand

MS154
in ch i key: ALKKWBPMCDDKKA-UHFFFAOYSA-N
comment: MS154 is a PROTAC (proteolysis targeting chimera). It is a hybrid molecule that simultaneously inhibits EGFR kinase activity and targets EGFR for destruction via ubiquitination and proteasomal degradation <Reference id=38642/>. The kinase inhibitor portion of the molecule is derived from the first generation EGFR inhibitor <Ligand id=4941/> and it uses a cereblon (CRBN) ligand to engage the E3 ligase system.
iupac name: 3-(4-(3-((4-((3-Chloro-4-fluorophenyl)amino)-7-methoxyquinazolin-6-yl)oxy)propyl)piperazin-1-yl)-N-(8-((2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindolin-4-yl)oxy)octyl)propanamide
synonym: compound 10 [PMID: 31895569]
approved: f
ligand name: MS154
type: SyntheticOrganicLigand

MS39
in ch i key: HLFLODKZIGYHNR-LTEFSYCBSA-N
comment: MS39 is a PROTAC (proteolysis targeting chimera). It is a hybrid molecule that simultaneously inhibits EGFR kinase activity and targets EGFR for destruction via ubiquitination and proteasomal degradation <Reference id=38642/>. The kinase inhibitor portion of the molecule is derived from the first generation EGFR inhibitor <Ligand id=4941/> and it uses a VHL ligand to engage the E3 ligase system.
iupac name: (2S,4R)-1-((S)-2-(11-(4-(3-((4-((3-Chloro-4-fluorophenyl)amino)-7-methoxyquinazolin-6-yl)oxy)propyl)piperazin-1-yl)-11-oxoundecanamido)-3,3-dimethylbutanoyl)-4-hydroxy-N-(4-(4-methylthiazol-5-yl)benzyl)pyrrolidine-2-carboxamide
synonym: compound 6 [PMID: 31895569]
approved: f
ligand name: MS39
type: SyntheticOrganicLigand

GSK2292767
in ch i key: NLUPPCTVKHDVIQ-GASCZTMLSA-N
in ch i: InChI=1S/C24H28N6O5S/c1-14-11-30(12-15(2)34-14)13-18-9-26-23(35-18)19-5-16(6-21-20(19)10-27-28-21)17-7-22(29-36(4,31)32)24(33-3)25-8-17/h5-10,14-15,29H,11-13H2,1-4H3,(H,27,28)/t14-,15+
comment: GSK2292767 is a selective PI3Kδ inhibitor that was developed as a back-up compound to clinical lead <Ligand id=9425/> (GSK2269557) <Reference id=31956/>.
iupac name: N-[5-[4-[5-[[(2S,6R)-2,6-dimethylmorpholin-4-yl]methyl]-1,3-oxazol-2-yl]-1H-indazol-6-yl]-2-methoxypyridin-3-yl]methanesulfonamide
synonym: GSK-2292767
synonym: GSK 2292767
synonym: compound 3 [PMID: 26301626]
synonym: compound 2 [PMID: 30532965]
approved: f
ligand name: GSK2292767
type: SyntheticOrganicLigand

itacnosertib
in ch i key: XSQKEVGTZSBVBR-UHFFFAOYSA-N
in ch i: InChI=1S/C26H28N8O/c1-33-14-16-34(17-15-33)22-9-8-19(18-23(22)35-2)30-26-29-13-10-24(32-26)31-21-7-5-12-28-25(21)20-6-3-4-11-27-20/h3-13,18H,14-17H2,1-2H3,(H2,29,30,31,32)
comment: The chemical structure that was submitted to the WHO for the INN itacnosertib is identical to the structure of example 11 that is claimed in Tolero Pharmaceuticals' patent WO2014151871A9 <Reference id=38637/>. The INN submission declares itacnosertib as a 'serine/threonine kinase inhibitor'. Data presented in WO2014151871A9 provide evidence of example 11's activity as an inhibitor of the activin A receptor type 1 (ACVR1; a.k.a. ALK2) which is a Type I receptor serine/threonine kinase. Tolero have declared an ACVR1-targeting oncology programme on their pipeline webpage. The research code provided is TP-0184, but to date (Dec 2020) there has been no formal name>structure disclosure for this compound.
iupac name: 2-N-[3-methoxy-4-(4-methylpiperazin-1-yl)phenyl]-4-N-(2-pyridin-2-ylpyridin-3-yl)pyrimidine-2,4-diamine
synonym: example 11 [WO2014151871A9]
synonym: TP-0184
synonym: TP0184
approved: f
ligand name: itacnosertib
type: SyntheticOrganicLigand

tegafur
canonical SMILES: O=c1[nH]c(=O)n(cc1F)C1CCCO1
isomeric SMILES: O=c1[nH]c(=O)n(cc1F)C1CCCO1
in ch i key: WFWLQNSHRPWKFK-UHFFFAOYSA-N
in ch i: InChI=1S/C8H9FN2O3/c9-5-4-11(6-2-1-3-14-6)8(13)10-7(5)12/h4,6H,1-3H2,(H,10,12,13)
comment: Like <Ligand id=6799/> and <Ligand id=4801/>, tegafur is a prodrug of the chemotherapeutic agent <Ligand id=4789/>. It is orally active. The INN specifies tegafur as a racemic mixture of enantiomers. We show the molecule without specified stereochemistry to represent the mixture.
iupac name: 5-fluoro-1-(oxolan-2-yl)pyrimidine-2,4-dione
xref: CHEMBL20883
synonym: FT-207
synonym: FT207
synonym: Florafur®
synonym: Ftorafur®
approved: t
ligand name: tegafur
type: SyntheticOrganicLigand

orelabrutinib
in ch i key: MZPVEMOYADUARK-UHFFFAOYSA-N
in ch i: InChI=1S/C26H25N3O3/c1-2-24(30)29-16-14-18(15-17-29)23-13-12-22(26(27)31)25(28-23)19-8-10-21(11-9-19)32-20-6-4-3-5-7-20/h2-13,18H,1,14-17H2,(H2,27,31)
comment: The chemical structure that was submitted to the WHO for the INN orelabrutinib, is identical to the structure of example 3 that is claimed as a BTK inhibitor in patent WO2015048662A2 <Reference id=38632/>. The inhibitors in WO2015048662A2 are claimed for their potential to treat cancers <Reference id=41904/> and inflammatory/autoimmune diseases that are mediated, at least in part, by Bruton's tyrosine kinase (BTK). Innocare Pharma have declared the ICP-022>orelabrutinib association on their company news webpage. Orelabrutinib is an orally administered, potent, irreversible and selective BTK-inhibitor.
synonym: example 3 [WO2015048662A2]
synonym: ICP022
synonym: ICP-022
approved: t
ligand name: orelabrutinib
type: SyntheticOrganicLigand

rezivertinib
in ch i key: BPMZUKYFIDPLEA-UHFFFAOYSA-N
in ch i: InChI=1S/C27H30N6O3/c1-6-26(34)29-22-15-21(24(35-5)16-25(22)36-14-13-32(2)3)31-27-28-12-11-20(30-27)19-17-33(4)23-10-8-7-9-18(19)23/h6-12,15-17H,1,13-14H2,2-5H3,(H,29,34)(H,28,30,31)
comment: The chemical structure submitted to the WHO for INN rezivertinib, is identical to the structure of example 1 that is claimed in patent WO2016094821A2 by Beta Pharma <Reference id=38631/>. This patent claims novel EGFR inhibitors that are active against mutated EGFRs that are found in cancers, i.e. third generation EGFR inhibitors. From Beta Pharma's declared pipeline, example 1 is likely to be BPI-7711, which is being investigated for the treatment of EGFRT790M-mutant non-small cell lung cancer. We await formal name>structure confirmation. Experimental evidence in WO2016094821A2 indicates that example 1 is orally bioavailable.
synonym: example 1 [WO2016094821A2]
approved: f
ligand name: rezivertinib
type: SyntheticOrganicLigand

hexadecanal
canonical SMILES: CCCCCCCCCCCCCCCC=O
isomeric SMILES: CCCCCCCCCCCCCCCC=O
in ch i key: NIOYUNMRJMEDGI-UHFFFAOYSA-N
in ch i: InChI=1S/C16H32O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17/h16H,2-15H2,1H3
iupac name: hexadecanal
xref: CHEMBL1235338
synonym: palmitaldehyde
approved: f
ligand name: hexadecanal
type: SyntheticOrganicLigand

zandelisib
in ch i key: WPFUFWIHMYZXSF-UHFFFAOYSA-N
in ch i: InChI=1S/C31H38F2N8O/c1-31(2,20-22-8-4-5-9-23(22)21-12-14-39(3)15-13-21)38-28-35-29(40-16-18-42-19-17-40)37-30(36-28)41-25-11-7-6-10-24(25)34-27(41)26(32)33/h4-11,21,26H,12-20H2,1-3H3,(H,35,36,37,38)
comment: The chemical structure of example 51 [WO2012135160A1] <Reference id=38628/> is identical to the structure that was submitted to the WHO for the INN zandelisib. In the INN submission zandelisib is designated as a PI3 kinase (PI3K) inhibitor and as an antineoplastic. Patent WO2012135160A1 was submitted by the PI3K inhibitor-focussed pharmaceutical company Pathway Therapeutics. Zandelisib has subsequently been declared as MEI Pharma's lead PI3Kδ inhibitor ME-401.
synonym: A35 [WO2012135160A1]
synonym: Example 51 [WO2012135160A1]
synonym: ME-401
synonym: ME401
approved: f
ligand name: zandelisib
type: SyntheticOrganicLigand

uzansertib
in ch i key: PTORCEYGCGXHDH-SGQXWQAPSA-N
in ch i: InChI=1S/C26H26F3N5O3/c1-12-10-34(11-17(30)25(12)36)24-13-5-8-20(35)22(13)31-9-19(24)33-26(37)18-7-6-16(29)23(32-18)21-14(27)3-2-4-15(21)28/h2-4,6-7,9,12,17,20,25,35-36H,5,8,10-11,30H2,1H3,(H,33,37)/t12-,17+,20+,25+/m1/s1
comment: Uzansertib (INCB053914) is a pan-PIM kinase inhibitor that was developed by Incyte Corporation as a novel anticancer agent <Reference id=38626/>. The chemical structure that was submitted to the WHO for the INN uzansertib is identical to the structure of INCB053914. INCB053914 is a Type 1, ATP-competitive inhibitor. The PIMs (PIM1, PIM2, and PIM3) are serine/threonine protein kinases that are important players in JAK/STAT and PI3K/AKT signalling pathways and in tumourigenesis. PIMs are known to be overexpressed in haematologic and solid tumours, and consequently PIM inhibitors are being developed and investigated for clinical anti-tumour potential.
synonym: INCB053914
synonym: INCB-053914
approved: f
ligand name: uzansertib
type: SyntheticOrganicLigand

tolebrutinib
in ch i key: KOEUOFPEZFUWRF-LJQANCHMSA-N
in ch i: InChI=1S/C26H25N5O3/c1-2-23(32)29-16-6-7-19(17-29)30-22-14-15-28-25(27)24(22)31(26(30)33)18-10-12-21(13-11-18)34-20-8-4-3-5-9-20/h2-5,8-15,19H,1,6-7,16-17H2,(H2,27,28)/t19-/m1/s1
comment: Tolebrutinib (PRN2246; SAR442168) is an oral and selective small molecule inhibitor of the enzyme Bruton tyrosine kinase (BTK) <Reference id=41086/>. It binds covalently and is brain-penetrant. The chemical structure that was submitted to the WHO for the INN tolebrutinib is identical to that of example 3 in Principia Biopharma's patent WO2016196840A1 <Reference id=38625/>.
iupac name: 4-amino-3-(4-phenoxyphenyl)-1-[(3R)-1-prop-2-enoylpiperidin-3-yl]imidazo[4,5-c]pyridin-2-one
synonym: example 3 [WO2016196840A1]
synonym: PRN2246
synonym: PRN-2246
synonym: BTK'168
synonym: SAR442168
approved: f
ligand name: tolebrutinib
type: SyntheticOrganicLigand

CE3F4
canonical SMILES: O=CN1C(C)CCc2c1cc(Br)c(c2Br)F
isomeric SMILES: O=CN1C(C)CCc2c1cc(Br)c(c2Br)F
in ch i key: ZZLQPWXVZCPUGC-UHFFFAOYSA-N
in ch i: InChI=1S/C11H10Br2FNO/c1-6-2-3-7-9(15(6)5-16)4-8(12)11(14)10(7)13/h4-6H,2-3H2,1H3
comment: Noncompetitive Epac1 inhibitor.
iupac name: 5,7-dibromo-6-fluoro-2-methyl-3,4-dihydro-2H-quinoline-1-carbaldehyde
approved: f
ligand name: CE3F4
type: SyntheticOrganicLigand

Sp-cAMPS
canonical SMILES: OC1C2OP(=S)(O)OCC2OC1n1cnc2c1ncnc2N
isomeric SMILES: OC1C2OP(=S)(O)OCC2OC1n1cnc2c1ncnc2N
in ch i key: SMPNJFHAPJOHPP-UHFFFAOYSA-N
in ch i: InChI=1S/C10H12N5O5PS/c11-8-5-9(13-2-12-8)15(3-14-5)10-6(16)7-4(19-10)1-18-21(17,22)20-7/h2-4,6-7,10,16H,1H2,(H,17,22)(H2,11,12,13)
comment: Cell-permeable cAMP analogue. Triethylammonium salt is used in assays (compound information available here: https://pubchem.ncbi.nlm.nih.gov/compound/57369926).
iupac name: 6-(6-aminopurin-9-yl)-2-hydroxy-2-sulfanylidene-4a,6,7,7a-tetrahydro-4H-furo[3,2-d][1,3,2]dioxaphosphinin-7-ol
approved: f
ligand name: Sp-cAMPS
type: SyntheticOrganicLigand

NANT
canonical SMILES: NCCNC[C@H](CCCN=C(N[N+](=O)[O-])N)N
isomeric SMILES: NCCNC[C@H](CCCN=C(N[N+](=O)[O-])N)N
in ch i key: RMSWBHUVFNFNIZ-ZETCQYMHSA-N
in ch i: InChI=1S/C8H21N7O2/c9-3-5-12-6-7(10)2-1-4-13-8(11)14-15(16)17/h7,12H,1-6,9-10H2,(H3,11,13,14)/t7-/m0/s1
comment: Cell-permeable, selective inhibitor of nNOS (Neuronal Nitric Oxide Synthase). Tris(trifluoroacetate) salt is used in assays (information available here: https://pubchem.ncbi.nlm.nih.gov/compound/71311606).
iupac name: 2-[(4S)-4-amino-5-(2-aminoethylamino)pentyl]-1-nitroguanidine
synonym: nNOS inhibitor I
approved: f
ligand name: NANT
type: SyntheticOrganicLigand

cPTIO
canonical SMILES: OC(=O)c1ccc(cc1)C1=[N+]([O-])C(C(N1[O])(C)C)(C)C
isomeric SMILES: OC(=O)c1ccc(cc1)C1=[N+]([O-])C(C(N1[O])(C)C)(C)C
in ch i key: KWNDLWPKCDMGTN-UHFFFAOYSA-N
in ch i: InChI=1S/C14H17N2O4/c1-13(2)14(3,4)16(20)11(15(13)19)9-5-7-10(8-6-9)12(17)18/h5-8H,1-4H3,(H,17,18)
comment: cPTIO is used in assays as a cell-permeating nitric oxide scavenger.
iupac name: 2-4-carboxyphenyl-4,4,5,5-tetramethylimidazoline-1-oxyl-3-oxide
synonym: carboxy-PTIO
approved: f
ligand name: cPTIO
type: SyntheticOrganicLigand

Rp-8-Br-cGMPS
in ch i key: KRYIOQOBMVFLBO-CIZWMVDRSA-M
comment: cGMP blocker. Sodium salt is used in assays (compound information is available here: https://pubchem.ncbi.nlm.nih.gov/compound/136240563).
iupac name: (4aR,6R,7R,7aS)-6-(2-amino-8-bromo-6-oxo-6,9-dihydro-3H-purin-9-yl)-7-hydroxy-2-sulfanylidene-hexahydro-2λ⁵-furo[3,2-d][1,3,2]dioxaphosphinin-2-olate
approved: f
ligand name: Rp-8-Br-cGMPS
type: SyntheticOrganicLigand

myr-PKI
in ch i key: GQPQKQWUUHDDIS-JDLJUXOTSA-N
comment: Cell-permeable protein kinase A inhibitor.
synonym: Protein kinase inhibitor-(14-22)-amide, myristoylated
approved: f
ligand name: myr-PKI
type: PeptideLigand

compound T.14
isomeric SMILES: COc1ccc(cc1)/C=C/c1cccc(c1)NC(=O)Nc1ccc(cc1)Cl
in ch i key: VGWVPSZVSVONQT-AATRIKPKSA-N
in ch i: InChI=1S/C22H19ClN2O2/c1-27-21-13-7-16(8-14-21)5-6-17-3-2-4-20(15-17)25-22(26)24-19-11-9-18(23)10-12-19/h2-15H,1H3,(H2,24,25,26)/b6-5+
comment: T.14 is a dual action compound that acts as an inhibitor of VEGFR2 (KDR) and the PD-L1 protein <Reference id=37777/>. Functionally it has antiangiogenic and immunomodulator actions, that are indicative of experimental anti-tumour potential.
iupac name: 3-(4-chlorophenyl)-1-{3-[(1E)-2-(4-methoxyphenyl)ethenyl]phenyl}urea
approved: f
ligand name: compound T.14
type: SyntheticOrganicLigand

seralutinib
in ch i key: JHJNPOSPVGRIAN-SFHVURJKSA-N
in ch i: InChI=1S/C27H27N5O3/c1-17-10-21(14-28-13-17)27(33)31-22-7-5-6-19(11-22)18(2)30-26-16-29-15-23(32-26)20-8-9-24(34-3)25(12-20)35-4/h5-16,18H,1-4H3,(H,30,32)(H,31,33)/t18-/m0/s1
comment: Seralutinib (PK10571; Structure 2a; GB002) is a small molecule inhibitor of platelet-derived growth factor receptors A and B (PDGFRα, PDGFRβ; receptor tyrosine kinases) <Reference id=38624/>. It was developed to target the PDGF pathway as a therepuetic modality for the treatment of pulmonary arterial hypertension (PAH). PK10571 is being progressed for PAH by Gossamer Bio in collaboration with Pulmokine. Inhibition of PDGFRα/β is predicted to stop and/or reverse the vascular remodeling associated with PAH and thereby improve cardiopulmonary hemodynamics in these patients.
iupac name: N-[3-[(1S)-1-[[6-(3,4-dimethoxyphenyl)pyrazin-2-yl]amino]ethyl]phenyl]-5-methylpyridine-3-carboxamide
synonym: Gb002
synonym: structure 2a [WO2014110200A1]
synonym: PK-10571
synonym: GB-002
synonym: PK10571
approved: f
ligand name: seralutinib
type: SyntheticOrganicLigand

brompheniramine
canonical SMILES: CN(CCC(c1ccccn1)c1ccc(cc1)Br)C
isomeric SMILES: CN(CCC(c1ccccn1)c1ccc(cc1)Br)C
in ch i key: ZDIGNSYAACHWNL-UHFFFAOYSA-N
in ch i: InChI=1S/C16H19BrN2/c1-19(2)12-10-15(16-5-3-4-11-18-16)13-6-8-14(17)9-7-13/h3-9,11,15H,10,12H2,1-2H3
comment: Brompheniramine is a racemic mixture of stereoisomers. We show the non-isomeric molecule to represent the mixture. The pharmacologically active isomer is <Ligand id=7588/>.
iupac name: [3-(4-bromophenyl)-3-(pyridin-2-yl)propyl]dimethylamine
xref: CHEMBL811
synonym: Dimetane
synonym: Dimetane-Ten
synonym: brompheniramine maleate
synonym: Bromfed®
synonym: Dimetapp®
synonym: Bromfenex
synonym: Lodrane
approved: t
ligand name: brompheniramine
type: SyntheticOrganicLigand

compound 28 [PMID: 31188540]
in ch i key: DUBVSWHYPDKVEA-UHFFFAOYSA-N
comment: Compound 28 is the optimized lead from a novel class of antimalarial compounds based on an aminoacetamide scaffold <Reference id=39422/>. The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
approved: f
ligand name: compound 28 [PMID: 31188540]
type: SyntheticOrganicLigand

WEHI-842
in ch i key: VAHRPHLZONNTFF-NUISNXNRSA-N
in ch i: InChI=1S/C34H51N7O7/c1-22(2)19-27(28(42)20-29(43)37-17-15-24-11-7-5-8-12-24)38-32(45)30(23(3)4)40-31(44)26(16-18-48-41-33(35)36)39-34(46)47-21-25-13-9-6-10-14-25/h5-14,22-23,26-28,30,42H,15-21H2,1-4H3,(H,37,43)(H,38,45)(H,39,46)(H,40,44)(H4,35,36,41)/t26-,27-,28-,30-/m0/s1
comment: WEHI-842 was developed as a potent peptidomimetic inhibitor of Plasmodium plasmepsin V (PMV), a promising target for antimalarial drug development <Reference id=38629/>. The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
iupac name: benzyl N-[(2S)-4-(diaminomethylideneamino)oxy-1-[[(2S)-1-[[(3S,4S)-3-hydroxy-6-methyl-1-oxo-1-(2-phenylethylamino)heptan-4-yl]amino]-3-methyl-1-oxobutan-2-yl]amino]-1-oxobutan-2-yl]carbamate
xref: CHEMBL3782104
approved: f
ligand name: WEHI-842
type: SyntheticOrganicLigand

UFM24
canonical SMILES: COc1cc2oc(cc(=O)c2c(c1O)OC)c1ccccc1
isomeric SMILES: COc1cc2oc(cc(=O)c2c(c1O)OC)c1ccccc1
in ch i key: YLSUKCVZCXUJBF-UHFFFAOYSA-N
in ch i: InChI=1S/C17H14O5/c1-20-14-9-13-15(17(21-2)16(14)19)11(18)8-12(22-13)10-6-4-3-5-7-10/h3-9,19H,1-2H3
comment: UFM24 is a flavone extracted from the Annonaceae Uvaria flexuosa <Reference id=34665/>. It exhibits anti-inflammatory effects that are mediated by inhibition of PDE4 cAMP phosphodiesterases in neutrophils. The anti-inflammatory activities (inhibition of superoxide anion generation and elastase release from human neutrophils in response to fMLP) of seco-cyclohexenes and cyclohexenes isolated from Uvaria flexuosa leaves are reported by Hsu et al. (2016) <Reference id=34666/>.
xref: CHEMBL464108
approved: f
ligand name: UFM24
type: NaturalProductLigand

balovaptan
in ch i key: GMPZPHGHNDMRKL-RZDIXWSQSA-N
in ch i: InChI=1S/C22H24ClN5O/c1-27-13-16-12-17(23)7-10-19(16)28-20(14-27)25-26-22(28)15-5-8-18(9-6-15)29-21-4-2-3-11-24-21/h2-4,7,10-12,15,18H,5-6,8-9,13-14H2,1H3/t15-,18-
comment: Balovaptan ((RG7314, RO5285119) is a potent, selective, orally administered and brain-penetrant vasopressin 1A (V1A) receptor antagonist <Reference id=38620/>. It was designed by Hoffmann-La Roche as a treatment for autism spectrum disorder, but its clinical development has been terminated.
iupac name: 8-chloro-5-methyl-1-(4-pyridin-2-yloxycyclohexyl)-4,6-dihydro-[1,2,4]triazolo[4,3-a][1,4]benzodiazepine
synonym: compound 1 [PMID: 31951127]
synonym: RG7314
synonym: RG-7314
synonym: RO5285119
synonym: RO-5285119
approved: f
ligand name: balovaptan
type: SyntheticOrganicLigand

BCH070
in ch i key: VKLMWXASUNVKHV-UHFFFAOYSA-N
in ch i: InChI=1S/C26H18ClN3O/c27-19-12-10-18(11-13-19)25-29-24-9-5-4-8-23(24)26(30-25)28-20-14-16-22(17-15-20)31-21-6-2-1-3-7-21/h1-17H,(H,28,29,30)
comment: BCH070 is lead antimalarial drug candidate, that with further optimization shows promise as a combination therapy with artemisinin to treat multidrug-resistant malaria <Reference id=38621/>.
iupac name: 2-(4-chlorophenyl)-N-[4-(phenoxy)phenyl]quinazolin-4-amine
approved: f
ligand name: BCH070
type: SyntheticOrganicLigand

reproxalap
canonical SMILES: Clc1ccc2c(c1)cc(c(n2)C(O)(C)C)N
isomeric SMILES: Clc1ccc2c(c1)cc(c(n2)C(O)(C)C)N
in ch i key: GUHFUVLKYSQIOQ-UHFFFAOYSA-N
in ch i: InChI=1S/C12H13ClN2O/c1-12(2,16)11-9(14)6-7-5-8(13)3-4-10(7)15-11/h3-6,16H,14H2,1-2H3
comment: Reproxalap is a novel small molecule that acts as a molecular trap for pro-inflammatory Reactive Aldehyde Species (RASP) that was developed by Aldeyra Therapeutics. Reproxalap (as example 5; NS2) and its uses are claimed in Aldeyra patent WO2018039197A1 <Reference id=38619/>.
iupac name: 2-(3-amino-6-chloroquinolin-2-yl)propan-2-ol
synonym: ADX-102
synonym: ADX102
synonym: NS-2
synonym: NS2
synonym: example 5 [WO2018039197A1]
approved: f
ligand name: reproxalap
type: SyntheticOrganicLigand

GSK030
in ch i key: BAABPIIOLPSIKR-UHFFFAOYSA-N
comment: GSK030 is an improved molecule from the thiotriazole series of antimalarial compounds <Reference id=40243/>. The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
iupac name: 2-[[5-(3,5-dichloropyridin-4-yl)-1H-1,2,4-triazol-3-yl]sulfanyl]-1-(1H-indol-3-yl)propan-1-one
synonym: GSK3212030A
approved: f
ligand name: GSK030
type: SyntheticOrganicLigand

CJ-15,801
canonical SMILES: OCC([C@H](C(=O)N/C=C/C(=O)O)O)(C)C
isomeric SMILES: OCC([C@H](C(=O)N/C=C/C(=O)O)O)(C)C
in ch i key: HWKKTJQAKVPKTK-SDLBARTOSA-N
in ch i: InChI=1S/C9H15NO5/c1-9(2,5-11)7(14)8(15)10-4-3-6(12)13/h3-4,7,11,14H,5H2,1-2H3,(H,10,15)(H,12,13)/b4-3+/t7-/m0/s1
comment: CJ-15,801 is a novel antibacterial, isolated from the fermentation broth of the fungus, Seimatosporium <Reference id=39400/>. It is a structural analogue of <Ligand id=4668/>. The compound inhibits the growth of drug resistant strains of Staphylococcus aureus and also has antimalarial activity <Reference id=39401/>.
iupac name: (E)-3-[[(2R)-2,4-dihydroxy-3,3-dimethylbutanoyl]amino]prop-2-enoic acid
xref: CHEMBL4164243
synonym: CJ-15801
approved: f
ligand name: CJ-15,801
type: NaturalProductLigand

metamizole
in ch i key: LVWZTYCIRDMTEY-UHFFFAOYSA-N
in ch i: InChI=1S/C13H17N3O4S/c1-10-12(14(2)9-21(18,19)20)13(17)16(15(10)3)11-7-5-4-6-8-11/h4-8H,9H2,1-3H3,(H,18,19,20)
comment: Metamizole (or dipyrone) is a non-addictive analgesic with analgesic, antipyretic and spasmolytic effects. It is indicated for severe acute and chronic pain and also for fever which is not responding to other treatments. Although it is available over-the-counter in some countries, it is prescription or banned in other countries, due to its potential for adverse events, including agranulocytosis.
iupac name: [(1,5-dimethyl-3-oxo-2-phenylpyrazol-4-yl)-methylamino]methanesulfonic acid
synonym: dipyrone
approved: f
ligand name: metamizole
type: SyntheticOrganicLigand

compound 3 [PMID: 31804822]
in ch i key: RQBUNBWHIATPNI-WQWWALRQSA-N
comment: Compound 3 is a PROTAC (proteolysis targeting chimera). It is a hybrid molecule that simultaneously inhibits MEK kinase activity and recruits E3 ligase via a Von Hippel-Lindau ligand to promote proteasomal degradation of MEK protein <Reference id=38601/>. The kinase inhibitor component of the molecule is an analogue of the allosteric MEK inhibitor <Ligand id=7942/>.
approved: f
ligand name: compound 3 [PMID: 31804822]
type: SyntheticOrganicLigand

AZD3965
in ch i key: PRNXOFBDXNTIFG-FQEVSTJZSA-N
comment: AZD3965 is an inhibitor of the monocarboxylate (lactate) transporter MCT1 (SLC16A1) <Reference id=38595/>. Eklevated MCT1 expression has been reported in a range of solid tumours <Reference id=38598/> and it is functionally essential in certain lymphomas which are highly dependent on the glycolytic metabolic pathway <Reference id=38597/>. It appears that cancer cells exploit MCT1 to efflux lactate so as to prevent intracellular acidification so as to prevent metabolic catastrophe. MCT1 inhibitors are being investigated for their potential to inhibit glycolysis and tumour growth.
iupac name: 5-[(4S)-4-hydroxy-4-methyl-1,2-oxazolidine-2-carbonyl]-3-methyl-6-[[5-methyl-3-(trifluoromethyl)-1H-pyrazol-4-yl]methyl]-1-propan-2-ylthieno[2,3-d]pyrimidine-2,4-dione
synonym: AZD-3965
approved: f
ligand name: AZD3965
type: SyntheticOrganicLigand

compound 2h [PMID: 30664827]
in ch i key: REDUQXCPUSNJOL-UHFFFAOYSA-N
in ch i: InChI=1S/C27H29N3O4/c1-19(2)22-12-14-24(15-13-22)27(33)30(17-21-8-10-23(11-9-21)26(32)29-34)18-25(31)28-16-20-6-4-3-5-7-20/h3-15,19,34H,16-18H2,1-2H3,(H,28,31)(H,29,32)
comment: Compound 2h is the hit compound from a series of dual-stage antiplasmodial HDAC inhibitors <Reference id=38594/><Reference id=38593/>.
iupac name: N-(2-(benzylamino)-2-oxoethyl)-N-(4-(hydroxycarbamoyl)benzyl)-4-isopropylbenzamide
approved: f
ligand name: compound 2h [PMID: 30664827]
type: SyntheticOrganicLigand

TG11-77
in ch i key: NZOAMVGASFFEJH-UHFFFAOYSA-N
in ch i: InChI=1S/C23H24N6O/c1-14-10-15(2)27-21(11-14)29-23-25-12-17(13-26-23)22(30)24-9-8-18-16(3)28-20-7-5-4-6-19(18)20/h4-7,10-13,28H,8-9H2,1-3H3,(H,24,30)(H,25,26,27,29)
comment: TG11-77 is reported as a selective, brain-penetrant EP2 receptor antagonist that is suitable for use in models of central nervous system diseases and inflammatory disorders <Reference id=38592/>. The hydrochloride salt was used in the majority of testing in <Reference id=38592/>. We show the structure for the parent molecule.
iupac name: 2-((4,6-Dimethylpyridin-2-yl)amino)-N-(2-(2-methyl-1H-indol-3-yl)ethyl)pyrimidine-5-carboxamide
synonym: compound 20o [PMID: 31904232]
approved: f
ligand name: TG11-77
type: SyntheticOrganicLigand

compound 26 [PMID: 31710475]
in ch i key: JGKCBXMHIQSQHJ-UHFFFAOYSA-N
in ch i: InChI=1S/C25H28N8O2/c1-31(2)11-12-33-16-19(15-27-33)18-8-9-22-20(14-18)25(34)29-23-7-5-6-21(28-23)24-30-26-17-32(24)10-3-4-13-35-22/h5-9,14-17H,3-4,10-13H2,1-2H3,(H,28,29,34)
comment: Compound 26 is a macrocyclic inhibitor of apoptosis signal-regulating kinase 1 (ASK1, MAP3K5) <Reference id=38508/>. Amongst the analogues designed and tested it is noted for its high level of CNS penetration, making it an ideal lead for examining the effect of ASK1 inhibition on inflammatory demyelination and neurodegeneration. Two previously reported ASK1 inhibitors have shown efficacy in the transgenic mouse SOD1 motor neurone disease model <Reference id=38586/>.
approved: f
ligand name: compound 26 [PMID: 31710475]
type: SyntheticOrganicLigand

VU0810464
in ch i key: HNJJARDABGKWSO-UHFFFAOYSA-N
in ch i: InChI=1S/C18H21ClFN3O/c1-12-9-17(23(22-12)14-5-3-2-4-6-14)21-18(24)11-13-7-8-16(20)15(19)10-13/h7-10,14H,2-6,11H2,1H3,(H,21,24)
comment: GIRK (Kir) channel activator with enhanced selectivity for GIRK1/2 (Kir3.1/Kir3.2) channels <Reference id=40471/>. It is more selective for neuronal Kir3 channels than <Ligand id=7768/>.
iupac name: 2-(3-chloro-4-fluorophenyl)-N-(1-cyclohexyl-3-methyl-1H-pyrazol-5-yl)acetamide
synonym: compound 8a [PMID: 28697302]
approved: f
ligand name: VU0810464
type: SyntheticOrganicLigand

AZD7648
in ch i key: XISVSTPEXYIKJL-UHFFFAOYSA-N
in ch i: InChI=1S/C18H20N8O2/c1-11-7-15-20-10-21-25(15)9-13(11)22-17-19-8-14-16(23-17)26(18(27)24(14)2)12-3-5-28-6-4-12/h7-10,12H,3-6H2,1-2H3,(H,19,22,23)
comment: AZD7648 is a selective inhibitor of DNA-dependent protein kinase (DNA-PK) <Reference id=38585/>. DNA-PK is responsible for recognising and repairing double-strand DNA breaks in damaged DNA, and is a cancer drug target. AZD7648 is orally bioavailable.
iupac name: 7-methyl-2-[(7-methyl-[1,2,4]triazolo[1,5-a]pyridin-6-yl)amino]-9-(oxan-4-yl)purin-8-one
synonym: AZD-7648
synonym: compound 16 [PMID: 31851518]
approved: f
ligand name: AZD7648
type: SyntheticOrganicLigand

cannabidiolic acid
in ch i key: WVOLTBSCXRRQFR-DLBZAZTESA-N
in ch i: InChI=1S/C22H30O4/c1-5-6-7-8-15-12-18(23)20(21(24)19(15)22(25)26)17-11-14(4)9-10-16(17)13(2)3/h11-12,16-17,23-24H,2,5-10H2,1,3-4H3,(H,25,26)/t16-,17+/m0/s1
comment: Cannabidiolic acid (CBDA) is a phytocannabinoid that is present at a significant concentration in Cannabis sativa <Reference id=38580/>. It slowly decarboxylates to <Ligand id=4150/> within the plant tissue. The decarboxylation process is accelerated by heat. To overcome its inherent instability, the more stable analogue cannabidiolic acid methyl ester (<Ligand id=10599/>) was synthesised <Reference id=38579/>. In in vivo models CBDA has been shown to produce anti-nausea <Reference id=38582/><Reference id=38583/><Reference id=38584/> and anxiolytic‐like effects <Reference id=38581/>.
iupac name: 2,4-dihydroxy-3-[(1R,6R)-3-methyl-6-prop-1-en-2-ylcyclohex-2-en-1-yl]-6-pentylbenzoic acid
xref: CHEMBL498672
synonym: CBDA
synonym: cannabidiol acid
approved: f
ligand name: cannabidiolic acid
type: SyntheticOrganicLigand

HU-580
in ch i key: BOYRUNMTTPSTKZ-PKOBYXMFSA-N
in ch i: InChI=1S/C23H32O4/c1-5-6-7-8-16-12-20(24)22(23(27)18(16)13-21(25)26)19-11-15(4)9-10-17(19)14(2)3/h11-12,17,19,24,27H,2,5-10,13H2,1,3-4H3,(H,25,26)/t17-,19+/m0/s1
comment: HU-580 (cannabidiolic acid methyl ester; CBDA-ME) is a stable synthetic analogue of the naturally occurring phytocannabinoid, <Ligand id=10600/> (CBDA ) <Reference id=38579/>. HU-580 has been shown to enhance maximal agonist activation of 5-HT1A receptors in a rat model, and produces anti-nausea and anti-anxiety effects which align with the biological profile reported for CBDA. The compound has efficacy in a rat model of peripheral neuropathic pain when administered at an early stage post-sciatic nerve surgery <Reference id=38952/>. Interestingly this effect is only observed in male rats, indicating potential sexual dimorphism in this response.
iupac name: 2-{2,4-dihydroxy-3-[(1R,6R)-3-methyl-6-(prop-1-en-2-yl)cyclohex-2-en-1-yl]-6-pentylphenyl}acetic acid
synonym: cannabidiolic acid methyl ester
synonym: CBDA-ME
synonym: HU580
approved: f
ligand name: HU-580
type: SyntheticOrganicLigand

compound 41 [PMID: 31855425]
in ch i key: ZWPJBXLFZFLGMV-OAQYLSRUSA-N
in ch i: InChI=1S/C25H33N3O8S/c1-31-5-6-37(29,30)27-23-8-18(10-26-25(23)32-2)17-7-19-12-33-16-22(19)24(9-17)36-15-21-11-28(3-4-35-21)20-13-34-14-20/h7-10,20-21,27H,3-6,11-16H2,1-2H3/t21-/m1/s1
comment: Compound 41 is a structurally novel, potent, selective and orally bioavailable PI3Kδ inhibitor <Reference id=38578/>. Results from this inhibitor optimisation study suggest that off-target inhibition of Vps34 is associated with in vivo toxicity in a rat PK model.
iupac name: (R)-2-Methoxy-N-(2-methoxy-5-(7-((4-(oxetan-3-yl)morpholin-2-yl)methoxy)-1,3-dihydroisobenzofuran-5-yl)pyridin-3-yl)ethanesulfonamide
approved: f
ligand name: compound 41 [PMID: 31855425]
type: SyntheticOrganicLigand

BAY-985
in ch i key: HZRJHVDNTDBTOZ-QGZVFWFLSA-N
in ch i: InChI=1S/C27H30F3N9O/c1-17(38-8-10-39(11-9-38)25(40)15-27(28,29)30)18-6-7-31-23(13-18)36-26-34-20-5-4-19(12-22(20)35-26)21-14-24(37(2)3)33-16-32-21/h4-7,12-14,16-17H,8-11,15H2,1-3H3,(H2,31,34,35,36)/t17-/m1/s1
comment: BAY-985 (compound 34) is an inhibitor of the IκB kinase (IKK)-related serine/threonine kinases TANK-binding kinase 1 (TBK1) and inhibitor of nuclear factor kappa B kinase subunit epsilon (IKKε) <Reference id=38577/>. BAY-985 has been contributed to the Structural Genomics Consortium's chemical probes set as a tool compound that is made freely available to the research community to enable extended investigation of TBK1 biology and its potential as a therapeutic target.
synonym: compound 34 [PMID: 31859507]
synonym: BAY985
approved: f
ligand name: BAY-985
type: SyntheticOrganicLigand

compound 29 [PMID: 31934767]
canonical SMILES: Clc1ccc(cc1)NC(=O)c1ccc(c(c1)C#Cc1cc(cnc1N)c1cnn(c1)C)C
isomeric SMILES: Clc1ccc(cc1)NC(=O)c1ccc(c(c1)C#Cc1cc(cnc1N)c1cnn(c1)C)C
in ch i key: JZKQBPWOWAPASE-UHFFFAOYSA-N
in ch i: InChI=1S/C25H20ClN5O/c1-16-3-4-19(25(32)30-23-9-7-22(26)8-10-23)11-17(16)5-6-18-12-20(13-28-24(18)27)21-14-29-31(2)15-21/h3-4,7-15H,1-2H3,(H2,27,28)(H,30,32)
comment: Compound 29 is reported as a colony-stimulating factor 1 receptor (CSF-1R) inhibitor <Reference id=38576/>. It was identified by high-throughput screening, and virtual docking and structure-activity-relationship (SAR) studies. The chemical structure of compound 29 represents a novel class of o-aminopyridyl alkynyl-based inhibitor for this kinase. Compound 29 elicits anti-inflammatory effects in vitro..
iupac name: 3-((2-Amino-5-(1-methyl-1H-pyrazol-4-yl)pyridin-3-yl)ethynyl)-N-(4-chlorophenyl)-4-methylbenzamide
approved: f
ligand name: compound 29 [PMID: 31934767]
type: SyntheticOrganicLigand

JR14a
in ch i key: OHRIKWUZKGNQKQ-IBGZPJMESA-N
comment: JR14a is reported as an antagonist of the Complement C3a receptor (C3aR) <Reference id=38574/>. It is orally active, and elicits anti-inflammatory effects in vitro and in vivo. It is a more potent antagonist than <Ligand id=3529/>.
iupac name: 5-(Bis(4-chlorophenyl)methyl)-3-methylthiophene-2-carbonyl)-l-arginine hydrochloride
approved: f
ligand name: JR14a
type: SyntheticOrganicLigand

peptide 1 [PMID: 31774287]
in ch i key: OBMZMSLWNNWEJA-XNCRXQDQSA-N
in ch i: InChI=1S/C51H62N12O7/c1-4-23-62-24-13-12-22-41(45(53)64)57-49(68)42(27-34-16-6-5-7-17-34)59-50(69)43(28-35-30-54-39-20-10-8-18-37(35)39)58-47(66)33(3)56-48(67)44(29-36-31-55-40-21-11-9-19-38(36)40)60-51(70)63(26-15-14-25-62)61-46(65)32(2)52/h4-11,16-21,30-33,41-44,54-55H,1,12-13,22-29,52H2,2-3H3,(H2,53,64)(H,56,67)(H,57,68)(H,58,66)(H,59,69)(H,60,70)(H,61,65)/t32-,33-,41-,42+,43-,44+/m0/s1
comment: Peptide 1 binds to the scavenger receptor CD36 and modulates its activity, as measured by NO production and cholesterol efflux <Reference id=38537/>.
iupac name: (4R,7S,10S,13R,16S)-1-[[(2S)-2-aminopropanoyl]amino]-13-benzyl-4,10-bis(1H-indol-3-ylmethyl)-7-methyl-2,5,8,11,14-pentaoxo-21-prop-2-enyl-1,3,6,9,12,15,21-heptazacyclopentacos-23-yne-16-carboxamide
approved: f
ligand name: peptide 1 [PMID: 31774287]
type: SyntheticOrganicLigand

padnarsertib
in ch i key: MRFOPLWJZULAQD-SWGQDTFXSA-N
in ch i: InChI=1S/C35H29F3N4O3/c36-28-9-7-24(8-10-28)30-19-26(23-3-5-25(6-4-23)34(44)42-15-13-35(37,38)14-16-42)17-27-18-29(45-33(27)30)21-41-32(43)12-2-22-1-11-31(39)40-20-22/h1-12,17-20H,13-16,21H2,(H2,39,40)(H,41,43)/b12-2+
comment: KPT-9274 is a small molecule that has reported inhibitory activity against PAK4 and NAMPT <Reference id=38559/><Reference id=38562/>. It is being developed by Karyopharm Therapeutics for anti-cancer efficacy in solid tumours <Reference id=38558/><Reference id=38560/> and in B cell malignancies <Reference id=38561/>. KPT-9274 is suggested to act as an allosteric modulator of PAK4 that does not interfere with the enzyme's kinase activity (in contrast to the type 1 ATP-competitive PAK kinase inhibitor <Ligand id=8937/>). It produces dose-dependent antitumour effects in solid and haematologic cell lines at low nanomolar concentrations <Reference id=38563/>. KPT-9274 is claimed as example 728 in patent WO2015003166A1 <Reference id=38564/>. The chemical structure of KPT-9274 is identical to that which was submitted to the WHO for the INN padnarsertib (proposed INN list 126, Jan 2022).
iupac name: (E)-3-(6-aminopyridin-3-yl)-N-[[5-[4-(4,4-difluoropiperidine-1-carbonyl)phenyl]-7-(4-fluorophenyl)-1-benzofuran-2-yl]methyl]prop-2-enamide
synonym: PAK4-IN-1
synonym: KPT9274
synonym: KPT-9274
approved: f
ligand name: padnarsertib
type: SyntheticOrganicLigand

topiroxostat
canonical SMILES: N#Cc1nccc(c1)c1n[nH]c(n1)c1ccncc1
isomeric SMILES: N#Cc1nccc(c1)c1n[nH]c(n1)c1ccncc1
in ch i key: UBVZQGOVTLIHLH-UHFFFAOYSA-N
in ch i: InChI=1S/C13H8N6/c14-8-11-7-10(3-6-16-11)13-17-12(18-19-13)9-1-4-15-5-2-9/h1-7H,(H,17,18,19)
comment: Selective xanthine oxidase inhibitor developed for treatment and management of hyperuricemia and gout.
iupac name: 4-(5-pyridin-4-yl-1H-1,2,4-triazol-3-yl)pyridine-2-carbonitrile
synonym: Topiloric
synonym: Uriadec
approved: f
ligand name: topiroxostat
type: SyntheticOrganicLigand

compound 3c [PMID: 30360354]
in ch i key: WYIBLRVRRGCPGV-FQYZGFJBSA-N
comment: Compound 3c acts as an antagonist of the scavenger receptor CD36 <Reference id=38535/>. Structurally it is an azasulfurylpeptide derivative of the synthetic hexapeptide growth hormone releasing peptide-6 (<Ligand id=1093/>) that has reported affinity for both CD36 and the ghrelin receptor (growth hormone secretagogue receptor).
synonym: azasulfuryl-p-fluorophenylalanine-4-[As(4-F)F4]-GHRP-6
synonym: [As(4-F)F4]-GHRP-6
synonym: H-His-D-Trp-Ala-(4-F)AsF-D-Phe-Lys-NH2
approved: f
ligand name: compound 3c [PMID: 30360354]
type: PeptideLigand

(S)-dimetindene
canonical SMILES: CN(CCC1=C(C(c2ccccn2)C)c2c(C1)cccc2)C
in ch i key: MVMQESMQSYOVGV-OAHLLOKOSA-N
in ch i: InChI=1S/C20H24N2/c1-15(19-10-6-7-12-21-19)20-17(11-13-22(2)3)14-16-8-4-5-9-18(16)20/h4-10,12,15H,11,13-14H2,1-3H3/t15-/m1/s1
comment: This is the (S)-enantiomer of the antihistamine drug <Ligand id=10101/>.
iupac name: N,N-dimethyl-2-[3-[(1S)-1-pyridin-2-ylethyl]-1H-inden-2-yl]ethanamine
xref: CHEMBL1493369
synonym: (+)-dimethindene
synonym: (+)-dimetindene
synonym: (S)-dimethindene
approved: f
ligand name: (S)-dimetindene
type: SyntheticOrganicLigand

PF-06821497
in ch i key: RXCVUHMIWHRLDF-HXUWFJFHSA-N
comment: PF-06821497 is an orally active inhibitor of the histone methyltransferase, enhancer of zeste homolog 2 (EZH2), that was developed by Pfizer for antineoplastic potential <Reference id=38382/>. Inhibition of EZH2 activity reduces mono-, di-, and trimethylation of lysine 27 on histone H3 (H3K27me, me2, and me3), and this ultimately leads to an antiproliferative effect on susceptible cancer cells (i.e. where aberrant EZH2-mediated epigenetic alterations are driving tumour initiation and progression).
iupac name: 5,8-dichloro-2-[(4-methoxy-6-methyl-2-oxo-1H-pyridin-3-yl)methyl]-7-[(R)-methoxy(oxetan-3-yl)methyl]-3,4-dihydroisoquinolin-1-one
xref: CHEMBL4080228
synonym: PF06821497
synonym: compound 23a [PMID: 29211475]
approved: f
ligand name: PF-06821497
type: SyntheticOrganicLigand

compound 18c [PMID:19143533]
in ch i key: FCBOUJYKAGWYQM-DEOSSOPVSA-N
in ch i: InChI=1S/C32H35N3O6/c1-38-27-19-23(20-28(39-2)31(27)40-3)30-26(32(37)33-16-17-41-25-12-8-5-9-13-25)14-15-29(35-30)34-24(21-36)18-22-10-6-4-7-11-22/h4-15,19-20,24,36H,16-18,21H2,1-3H3,(H,33,37)(H,34,35)/t24-/m0/s1
comment: Compound 18c is a calcium-sensing receptor (CaSR) negative allosteric modulator (NAM) <Reference id=38544/>. It utilises a second allosteric binding site that is topographically distinct from the NPS2143 binding site <Reference id=38591/>. Negative modulation of CaSR promotes release of parathyroid hormone (PTH). Transient release of PTH elicits a bone anabolic response, so molecules that act as rapid/transient negative CaSR modulators are being explored for potential as novel agents to treat bone-loss diseases.
iupac name: (S)-6-((1-hydroxy-3-phenylpropan-2-yl)amino)-N-(2-phenoxyethyl)-2-(3,4,5-trimethoxyphenyl)nicotinamide
xref: CHEMBL457071
synonym: BMS compound 1
approved: f
ligand name: compound 18c [PMID:19143533]
type: SyntheticOrganicLigand

UCM-05194
in ch i key: IHTMTVSBHMPLJC-GOSISDBHSA-N
in ch i: InChI=1S/C19H30BrO6P/c20-15-18(16-25-27(22,23)24)26-19(21)14-10-5-3-1-2-4-7-11-17-12-8-6-9-13-17/h6,8-9,12-13,18H,1-5,7,10-11,14-16H2,(H2,22,23,24)/t18-/m1/s1
comment: UCM-05194 (compound (S)-17) is a LPA1 receptor agonist <Reference id=38539/>. UCM-05194-mediated internalisation of the receptor induces functional inactivation of LPA1 cellular effects in vitro, which translates to attenuation of pain perception in an animal model of neuropathic pain. It is therefore a suitable tool for assessing LPA1-mediated effects in vitro and for evaluating the potential of in vivo LPA1 receptor modulation as a strategy for therapeutic intervention in neuropathic pain.
iupac name: (2S)-1-Bromo-3-(phosphonooxy)propan-2-yl 10-Phenyldecanoate
synonym: (S)-17 [PMID: 31790581]
synonym: UCM05194
synonym: UCM 05194
approved: f
ligand name: UCM-05194
type: SyntheticOrganicLigand

JNJ-27141491
in ch i key: SYARXICKXVXWNA-GFCCVEGCSA-N
comment: JNJ-27141491 is a reversible and noncompetitive (insurmountable) antagonist of the chemokine receptor CCR2 <Reference id=38534/>. It acts at an intracellular domain of the receptor and is orally active in transgenic mice that express human CCR2.
iupac name: methyl 3-[(1R)-1-(3,4-difluorophenyl)propyl]-5-(1,2-oxazol-5-yl)-2-sulfanylidene-1H-imidazole-4-carboxylate
synonym: JNJ27141491
approved: f
ligand name: JNJ-27141491
type: SyntheticOrganicLigand

compound 39 [PMID: 31742400]
in ch i key: KLBHHUODQVCBKX-UHFFFAOYSA-N
in ch i: InChI=1S/C15H15Cl2N5O/c1-7(2)12-9(6-8-4-3-5-10(16)11(8)17)13(23)22-15(19-12)20-14(18)21-22/h3-5,7H,6H2,1-2H3,(H3,18,19,20,21)
comment: Compound 39 is a dual antagonist of the CC-chemokine receptors CCR2 and CCR5 <Reference id=38531/>. It is one of the most potent lead molecules that were reported in this 2019 Journal of Medicinal Chemistry paper. Experiments measuring antagonism of CCL3-induced [35S]GTPγS binding indicates that 39 binds to an allosteric site of both target receptors, which is likely to be located on the intracellular face of the receptiors. The compound is described as an insurmountable antagonist.
iupac name: 2-Amino-6-(2,3-dichlorobenzyl)-5-isopropyl[1,2,4]triazolo[1,5-a]pyrimidin-7(4H)-one
approved: f
ligand name: compound 39 [PMID: 31742400]
type: SyntheticOrganicLigand

donecopride
in ch i key: FTRZTHFGTILUPE-UHFFFAOYSA-N
in ch i: InChI=1S/C22H33ClN2O2/c1-27-22-14-20(24)19(23)13-18(22)21(26)8-7-16-9-11-25(12-10-16)15-17-5-3-2-4-6-17/h13-14,16-17H,2-12,15,24H2,1H3
comment: Donecopride is a small molecule that exhibits potent dual actions as an acetylcholinesterase (AChE) inhibitor and as a partial 5-HT4 receptor agonist <Reference id=38527/>. It is a hybrid molecule that combines structural components from the AChE inhibitor <Ligand id=6599/>, and the 5-HT4 agonist <Ligand id=237/> <Reference id=38528/> <Reference id=38529/>. Donecopride is predicted to provide a combination of symptomatic and disease-modifying effects that are considered to offer therapeutic utility in Alzheimer's disease <Reference id=38590/><Reference id=38530/>.
iupac name: 1-(4-amino-5-chloro-2-methoxyphenyl)-3-[1-(cyclohexylmethyl)piperidin-4-yl]propan-1-one
xref: CHEMBL3417009
synonym: compound 1 [PMID: 25793650]
synonym: MR31147
approved: f
ligand name: donecopride
type: SyntheticOrganicLigand

ebselen
canonical SMILES: O=c1c2ccccc2[se]n1c1ccccc1
isomeric SMILES: O=c1c2ccccc2[se]n1c1ccccc1
in ch i key: DYEFUKCXAQOFHX-UHFFFAOYSA-N
in ch i: InChI=1S/C13H9NOSe/c15-13-11-8-4-5-9-12(11)16-14(13)10-6-2-1-3-7-10/h1-9H
comment: A synthetic organoselenium molecule with anti-inflammatory, anti-oxidant and cytoprotective activity, characterised as a small molecule Gq protein inhibitor. A bioRxiv preprint suggests that ebselen is a low micromolar, covalent, fast-binding inhibitor of papain-like protease (PL-pro) from SARS-CoV-2 <Reference id=39775/>. This study also reports that ebselen is less active against SARS-CoV, and binds more slowly to this enzyme homologue.
iupac name: 2-phenyl-1,2-benzoselenazol-3-one
approved: f
ligand name: ebselen
type: SyntheticOrganicLigand

compound 15b [PMID: 31811124]
in ch i key: HEZMXOWAEONYPI-UHFFFAOYSA-N
in ch i: InChI=1S/C34H39NO7/c36-30(26-17-19-28(20-18-26)41-22-9-2-1-4-11-25-12-5-3-6-13-25)23-27-14-10-15-29-33(27)42-31(34(39)40)24-35(29)21-8-7-16-32(37)38/h3,5-6,10,12-15,17-20,31H,1-2,4,7-9,11,16,21-24H2,(H,37,38)(H,39,40)
comment: Compound 15b is an antagonist of cysteinyl leukotriene G protein-coupled receptors CysLT1 and CysLT2 <Reference id=38526/>. It is approximately 200-fold selective for CysLT2 compared to CysLT1 in vitro.
iupac name: 4-(4-carboxybutyl)-8-(2-oxo-2-{4-[(6-phenylhexyl)oxy]phenyl}ethyl)-3,4-dihydro-2H-1,4-benzoxazine-2-carboxylic acid
approved: f
ligand name: compound 15b [PMID: 31811124]
type: SyntheticOrganicLigand

compound 13e [PMID: 31811124]
in ch i key: MUBSBSWICVQHHN-UHFFFAOYSA-N
in ch i: InChI=1S/C34H37NO8/c36-27(13-8-15-32(38)39)22-35-23-31(34(40)41)43-33-26(12-7-14-29(33)35)21-30(37)25-16-18-28(19-17-25)42-20-6-2-5-11-24-9-3-1-4-10-24/h1,3-4,7,9-10,12,14,16-19,31H,2,5-6,8,11,13,15,20-23H2,(H,38,39)(H,40,41)
comment: Compound 13e is an antagonist of cysteinyl leukotriene G protein-coupled receptors CysLT1 and CysLT2 <Reference id=38526/>. it is approximately 1800-fold selective for CysLT1 compared to CysLT2 in vitro.
iupac name: 4-(5-carboxy-2-oxopentyl)-8-(2-oxo-2-{4-[(5-phenylpentyl)oxy]phenyl}ethyl)-3,4-dihydro-2H-1,4-benzoxazine-2-carboxylic acid
approved: f
ligand name: compound 13e [PMID: 31811124]
type: SyntheticOrganicLigand

ONO-2570366
in ch i key: JCUVQOJHURMRKB-SANMLTNESA-N
comment: ONO-2570366 is an antagonist of the cysteinyl leukotriene receptors CysLT1 and CysLT2 <Reference id=38526/>. It has been used to elucidate the three dimensional structure of the CysLT2 receptor and its ligand-selectivity determinants.
iupac name: (2S)-4-(3-carboxypropyl)-8-[[4-[4-(2-chloro-5-fluorophenyl)butoxy]benzoyl]amino]-2,3-dihydro-1,4-benzoxazine-2-carboxylic acid
synonym: compound 11a [PMID: 31811124]
synonym: ONO2570366
approved: f
ligand name: ONO-2570366
type: SyntheticOrganicLigand

ARD-266
in ch i key: RTNONCBKGZNCJS-LJLQSONVSA-N
in ch i: InChI=1S/C52H59ClN6O7/c1-31(2)45(43-25-32(3)57-66-43)48(64)59-30-38(60)26-42(59)47(63)55-41(35-11-9-8-10-12-35)28-44(61)58-23-21-34(22-24-58)14-13-33-15-17-36(18-16-33)46(62)56-49-51(4,5)50(52(49,6)7)65-39-20-19-37(29-54)40(53)27-39/h8-12,15-20,25,27,31,34,38,41-42,45,49-50,60H,21-24,26,28,30H2,1-7H3,(H,55,63)(H,56,62)/t38-,41+,42+,45-,49-,50-/m1/s1
comment: ARD-266 is a potent proteolysis-targeting chimera (PROTAC) degrader of the androgen receptor (AR) <Reference id=38524/>. Its design highlights that using an E3 ligase ligand with low affinity (Ki of 2-3 μM) in a PROTAC can still achieve a very potent degrading effect against the AR. Ubiquitination and proteasomal degradation is mediated by the compound's ligand that binds to the VHL constituent of the VHL/cullin2 E3 ligase complex. The AR antagonist component of ARD-266 is the same as that utilised in the previously reported AR degrader, <Ligand id=10182/>.
synonym: compound 11 [PMID: 31804827]
approved: f
ligand name: ARD-266
type: SyntheticOrganicLigand

AS-252424
canonical SMILES: O=C1SC(=Cc2ccc(o2)c2ccc(cc2O)F)C(=O)N1
isomeric SMILES: O=C1S/C(=C/c2ccc(o2)c2ccc(cc2O)F)/C(=O)N1
in ch i key: OYYVWNDMOQPMGE-SDQBBNPISA-N
in ch i: InChI=1S/C14H8FNO4S/c15-7-1-3-9(10(17)5-7)11-4-2-8(20-11)6-12-13(18)16-14(19)21-12/h1-6,17H,(H,16,18,19)/b12-6-
comment: AS-252424 is an inhibitor of the lipid kinase PI3Kγ <Reference id=38521/>. In cellular assays it is selective for class IB PI3K-mediated effects.
iupac name: (5Z)-5-[[5-(4-fluoro-2-hydroxyphenyl)furan-2-yl]methylidene]-1,3-thiazolidine-2,4-dione
xref: CHEMBL379156
synonym: AS252424
synonym: AS 252424
synonym: compound 26 [PMID: 16789742]
approved: f
ligand name: AS-252424
type: SyntheticOrganicLigand

ABBV-3221
in ch i key: YFEYDNAKCSOOOG-YCXOGWGTSA-N
in ch i: InChI=1S/C30H37F3N2O6/c1-17-10-6-7-11-20(17)23-25(41-16-18-14-19(30(31,32)33)15-34-26(18)39-5)22(29(2,3)4)24(28(37)38)35(23)27(36)21-12-8-9-13-40-21/h6-7,10-11,14-15,21-25H,8-9,12-13,16H2,1-5H3,(H,37,38)/t21-,22+,23-,24-,25-/m0/s1
comment: ABBV-3221(GLPG-3221) is a novel cystic fibrosis transmembrane conductance regulator (CFTR) corrector that is being developed in a collaboration between AbbVie and Galapagos for the treatment of cystic fibrosis <Reference id=38516/>. It was designed to provide improved clinical efficacy when used in a triple combination with a CFTR potentiator and a second, but mechanistically distinct, corrector molecule.
iupac name: (2S,3R,4S,5S)-3-tert-Butyl-4-{[2-methoxy-5-(trifluoromethyl)pyridin-3-yl]methoxy}-5-(2-methylphenyl)-1-[(2S)-oxane-2-carbonyl]pyrrolidine-2-carboxylic acid
synonym: ABBV/GLPG-3221
synonym: compound 19 [PMID: 31749908]
approved: f
ligand name: ABBV-3221
type: SyntheticOrganicLigand

compound 32 [PMID: 31675166]
in ch i key: CZGQFMWYGXCTGQ-LEWJYISDSA-N
in ch i: InChI=1S/C24H24N4O3/c1-2-20(19-9-5-7-15-6-3-4-8-18(15)19)27-23(29)21-14-28(24(30)31-21)17-12-10-16(11-13-17)22(25)26/h3-13,20-21H,2,14H2,1H3,(H3,25,26)(H,27,29)/t20-,21+/m0/s1
comment: This compound is a small molecule inhibitor of kallikrein-related peptidase 6 (KLK6) <Reference id=38513/>. It is the most potent analogue that was identified using structure-guided design and optimisation of a lead molecule from a high-throughput screen. The PK/PD profile of 32 indicates that it is suitable as a tool compound to further explore the biology of KLK6 and its potential as a therapeutic drug target.
iupac name: (5R)‐3‐(4‐carbamimidoylphenyl)‐N‐((S)‐1‐(naphthalen‐1‐yl)propyl)‐2‐oxooxazolidine‐5‐carboxamide
approved: f
ligand name: compound 32 [PMID: 31675166]
type: SyntheticOrganicLigand

DKFZ‐251
in ch i key: OWHVQGGLXPNNBI-UHFFFAOYSA-N
in ch i: InChI=1S/C24H24N4O3/c1-15-20(19-11-7-8-12-21(19)25-15)13-23(30)31-14-22(29)26-24-16(2)27-28(17(24)3)18-9-5-4-6-10-18/h4-12,25H,13-14H2,1-3H3,(H,26,29)
comment: DKFZ-251 acts as an inhibitor of kallikrein related peptidase 6 (KLK6) <Reference id=38512/>. It is a useful tool compound to explore the role of KLK6 as a potential therapeutic drug target in pathologies such as cancer and neurodegenerative diseases.
iupac name: [2-[(3,5-dimethyl-1-phenylpyrazol-4-yl)amino]-2-oxoethyl] 2-(2-methyl-1H-indol-3-yl)acetate
synonym: compound 11 [PMID: 30212625]
approved: f
ligand name: DKFZ‐251
type: SyntheticOrganicLigand

compound 1 [Cruz-López et al., 2019]
in ch i key: PXBYPIWEYSTETR-UHFFFAOYSA-N
in ch i: InChI=1S/C28H28N14/c1-3-20-4-2-19(1)14-40-16-22(34-37-40)12-31-28-32-13-24-26(21-5-6-25(30-11-21)39-9-7-29-8-10-39)36-42(27(24)33-28)18-23-17-41(15-20)38-35-23/h1-6,11,13,16-17,29H,7-10,12,14-15,18H2,(H,31,32,33)
comment: This macrocyclic compound is reported as a selective inhibitor of AXL kinase activity <Reference id=38511/>
approved: f
ligand name: compound 1 [Cruz-López et al., 2019]
type: SyntheticOrganicLigand

OSTN (81-102)
in ch i key: KWLGDIDCTYJFLH-URZJMNTHSA-N
comment: This peptide is a variant of human <Ligand id=5036/>. It exhibits agonist activity at the GPCR, chemerin receptor 2 (GPR1) <Reference id=38463/>.
approved: f
ligand name: OSTN (81-102)
type: PeptideLigand

Pomc (141-162)
in ch i key: JKMUANZFHYBAQT-OZIQLYOYSA-N
comment: This peptide is a variant derived from human pro-opiomelanocortin (POMC). It exhibits agonist activity at the orphan GPCR, GPR68 <Reference id=38463/>.
approved: f
ligand name: Pomc (141-162)
type: PeptideLigand

CARTPT (76-96)
in ch i key: PNNVWALMJPZPKN-UNDUOMTFSA-N
comment: This peptide is a variant of human CART prepropeptide (CARTPT; also known as 'cocaine and amphetamine regulated transcript'). It exhibits agonist activity at the orphan GPCR, GPR68 <Reference id=38463/>.
approved: f
ligand name: CARTPT (76-96)
type: PeptideLigand

OSTN (115-133)
in ch i key: LBPSGCKOVGOHBM-ZGLUUWDISA-N
comment: This peptide is a variant of human <Ligand id=5036/>. It exhibits agonist activity at the orphan GPCR, GPR68 <Reference id=38463/>.
approved: f
ligand name: OSTN (115-133)
type: PeptideLigand

NMU (104-114)
in ch i key: LAHQIXAOZMTTQC-LEOUQZHDSA-N
comment: This peptide is a variant of <Ligand id=1470/>. It exhibits agonist activity at the orphan GPCR, bombesin receptor subtype 3 (BB3; BRS3) <Reference id=38463/>.
approved: f
ligand name: NMU (104-114)
type: PeptideLigand

ilaprazole
in ch i key: HRRXCXABAPSOCP-UHFFFAOYSA-N
in ch i: InChI=1S/C19H18N4O2S/c1-13-17(20-8-7-18(13)25-2)12-26(24)19-21-15-6-5-14(11-16(15)22-19)23-9-3-4-10-23/h3-11H,12H2,1-2H3,(H,21,22)
comment: Ilaprazole (IY-81149) is an irreversible proton pump inhibitor (PPI) <Reference id=38354/>. It is a prodrug that is converted to an active sulfenamide form that binds to cysteine sulfhydryl groups on the proton pump H+/K+ ATPase of gastric parietal cells, and thereby inhibits gastric acid secretion <Reference id=38355/>.
synonym: IY-81149
synonym: IY81149
synonym: Noltec®
approved: t
ligand name: ilaprazole
type: SyntheticOrganicLigand

GPR15L (71-81)
in ch i key: NLEQDIXNHJSWHA-UPULOONWSA-N
in ch i: InChI=1S/C58H91N13O13/c1-29(2)24-37(59)50(75)65-40(26-35-27-61-38-17-13-12-16-36(35)38)52(77)67-46(31(5)6)55(80)68-47(32(7)8)57(82)71-23-14-18-42(71)53(78)62-28-45(73)63-34(11)49(74)66-41(25-30(3)4)56(81)70-22-15-19-43(70)54(79)64-39(20-21-44(60)72)51(76)69-48(33(9)10)58(83)84/h12-13,16-17,27,29-34,37,39-43,46-48,61H,14-15,18-26,28,59H2,1-11H3,(H2,60,72)(H,62,78)(H,63,73)(H,64,79)(H,65,75)(H,66,74)(H,67,77)(H,68,80)(H,69,76)(H,83,84)/t34-,37-,39-,40-,41-,42-,43-,46-,47-,48-/m0/s1
comment: This peptide is a variant of <Ligand id=10567/>. It exhibits agonist activity at GPR15 <Reference id=38463/>.
approved: f
ligand name: GPR15L (71-81)
type: PeptideLigand

bamocaftor
in ch i key: IGEOJNMYRZUKIK-IBGZPJMESA-N
comment: Bamocaftor (VX-659) is a next-generation CFTR corrector class molecule <Reference id=38478/>. It is structurally related to <Ligand id=10552/> and like other corrector molecules was designed to improve CFTR protein processing and trafficking in the presence of the F508del mutation. Bamocaftor's mechanism of action is different from that of the first generation CFTR corrector <Ligand id=10199/> and its functional and clinical effects appear to be additive <Reference id=38478/>. As such a triple combination therapeutic with tezacaftor, izacaftor (a CFTR potentiator that increases CFTR channel gating activity) and bamocaftor increases CFTR function beyond that achieved by current standard of care dual therapy tezacaftor/izacaftor, and improves clinical symptoms in patients with cystic fibrosis with one or two F508del alleles <Reference id=38477/>.
synonym: VX-659
synonym: VX659
synonym: compound 1 [WO2018064632A1]
approved: f
ligand name: bamocaftor
type: SyntheticOrganicLigand

GPR15L
in ch i key: MKYBCIBFBPPBKT-QSWODBGPSA-N
comment: This peptide is a product of the human C10orf99 gene. It is proposed as an agonistic ligand of the orphan GPCR, GPR15, and has been referred to as GPR15L <Reference id=33963/>. Structurally, GPR15L is predicted to contain two intramolecular disulphide bonds, which implies a similarity to CC family cytokines. GPR15L has also been reported as a pruritogen that is produced in the skin, which induces mast cell degranulation via activation of the Mas-related G protein-coupled receptors (MRGPRs) <Reference id=43856/>. MRGPR-GPR15L-mediated itch and inflammation is independent of GPR15.
synonym: colon-derived SUSD2 binding factor
synonym: antimicrobial peptide-57
approved: f
ligand name: GPR15L
type: PeptideLigand

SAR439859
in ch i key: KISZAGQTIXIVAR-UHFFFAOYSA-N
comment: SAR439859 is a selective estrogen receptor degrader (SERD) <Reference id=38506/>. It was designed (by Sanofi) to have improved pharmacokinetic properties compared to the existing clinically used SERD, <Ligand id=1015/>. An X-ray structure of SAR439859 in complex with the ERα ligand binding domain indicates that the ligand occupies the orthosteric estradiol binding cavity.
iupac name: 6-(2,4-dichlorophenyl)-5-[4-[1-(3-fluoropropyl)pyrrolidin-3-yl]oxyphenyl]-8,9-dihydro-7H-benzo[7]annulene-2-carboxylic acid
synonym: SAR-439859
synonym: SAR 439859
synonym: compound 43d [PMID: 31721572]
approved: f
ligand name: SAR439859
type: SyntheticOrganicLigand

ERD-308
in ch i key: BQXUPNKLZNSUMC-YUQWMIPFSA-N
in ch i: InChI=1S/C55H65N5O9S2/c1-7-59(26-28-69-43-22-17-37(18-23-43)49(65)48-44-24-21-41(62)30-46(44)71-51(48)39-15-19-40(61)20-16-39)25-9-8-10-27-68-32-47(64)58-52(55(4,5)6)54(67)60-31-42(63)29-45(60)53(66)57-34(2)36-11-13-38(14-12-36)50-35(3)56-33-70-50/h11-24,30,33-34,42,45,52,61-63H,7-10,25-29,31-32H2,1-6H3,(H,57,66)(H,58,64)/t34-,42+,45-,52+/m0/s1
comment: ERD-308 is a small-molecule ERα degrader that was designed using the proteolysis targeting chimeras (PROTAC) model <Reference id=38505/>. It is a hybrid molecule that links together an ERα antagonist (a derivative of <Ligand id=2820/>) and a VHL ligand that engages the VHL E3 ligase to direct ERα receptors for ubiquitination and proteasomal degradation.
synonym: ERD308
synonym: compound 32 [PMID: 30990042]
approved: f
ligand name: ERD-308
type: SyntheticOrganicLigand

ARV-771
in ch i key: PQOGZKGXGLHDGS-QQRWPDCKSA-N
comment: ARV-771 is a small-molecule pan-BET degrader based on proteolysis-targeting chimera (PROTAC) technology <Reference id=38504/>. It targets the BET domain proteins BRD2/3/4 for VHL E3 ligase-mediated ubiquitination and proteasomal degradation. This mechanism effects suppression of the androgen receptor (AR) protein level and AR signalling. ARV-771 is efficacious in vivo, as demonstrated in two different mouse models of castration-resistant prostate cancer (CRPC).
synonym: ARV771
approved: f
ligand name: ARV-771
type: SyntheticOrganicLigand

MS432
in ch i key: KCBAMQOKOLXLOX-BSZYMOERSA-N
comment: MS432 is the first-reported mitogen-activated protein kinase kinase 1/2 (MEK1/2) degrader <Reference id=38503/>. Structurally MS432 is a hybrid molecule, combining a kinase-targeting ligand (based on <Ligand id=7935/>) with a VHL-engaging moeity In this case VHL ligand 2, (S,R,S)-AHPC-Me . These types of agents are known as PROTACs, or proteolysis targeting chimeras. It targets the kinases for VHL E3 ligase- and proteasome-mediated degradation. In vitro, the effect of MS432 is phenocopied by MEK1/2 knockdown. MS432 is bioavailable and suitable for in vivo studies.
iupac name: (2S,4R)-1-((S)-20-(tert-Butyl)-1-(3,4-difluoro-2-((2-fluoro-4-iodophenyl)amino)phenyl)-1,18-dioxo-3-oxa-2,7,19-triazahenicosan-21-oyl)-4-hydroxy-N-((S)-1-(4-(4-methylthiazol-5-yl)phenyl)ethyl)pyrrolidine-2-carboxamide
synonym: MS-432
synonym: compound 23 [PMID: 31730343]
approved: f
ligand name: MS432
type: SyntheticOrganicLigand

4-OMe-ARM1
canonical SMILES: COc1ccc(cc1)Cc1ccc(cc1)c1csc(n1)N
isomeric SMILES: COc1ccc(cc1)Cc1ccc(cc1)c1csc(n1)N
in ch i key: GGCCOFFVKJCRKJ-UHFFFAOYSA-N
in ch i: InChI=1S/C17H16N2OS/c1-20-15-8-4-13(5-9-15)10-12-2-6-14(7-3-12)16-11-21-17(18)19-16/h2-9,11H,10H2,1H3,(H2,18,19)
comment: 4-OMe-ARM1 is an activator of leukotriene A4 hydrolase aminopeptidase activity <Reference id=38502/>.
iupac name: 4-(4-{[4-(Methoxy)phenyl]methyl}phenyl)-1,3-thiazol-2-ylamine
synonym: compound 7 [PMID: 31751136]
approved: f
ligand name: 4-OMe-ARM1
type: SyntheticOrganicLigand

compound 15a
in ch i key: KCWRZNXFHSFVKD-RUZDIDTESA-N
in ch i: InChI=1S/C31H26ClN3O3/c1-2-9-25(19-10-4-3-5-11-19)35-30(36)20-16-17-21(23(18-20)31(37)38)28-22(12-8-13-24(28)32)29-33-26-14-6-7-15-27(26)34-29/h3-8,10-18,25H,2,9H2,1H3,(H,33,34)(H,35,36)(H,37,38)/t25-/m1/s1
comment: Compound 15a is a small-molecule agonist of the apelin receptor <Reference id=38491/>. It exhibits similar in vitro potency to the endogenous agonist <Ligand id=605/>, and binds to the orthosteric site of the receptor. Compound 15a was designed by Bristol-Myers Squibb Research and Development.
iupac name: 2-[2-(1H-benzimidazol-2-yl)-6-chlorophenyl]-5-[[(1R)-1-phenylbutyl]carbamoyl]benzoic acid
approved: f
ligand name: compound 15a
type: SyntheticOrganicLigand

DASA-58
in ch i key: GMHIOMMKSMSRLY-UHFFFAOYSA-N
in ch i: InChI=1S/C19H23N3O6S2/c20-15-3-1-4-16(13-15)29(23,24)21-7-2-8-22(10-9-21)30(25,26)17-5-6-18-19(14-17)28-12-11-27-18/h1,3-6,13-14H,2,7-12,20H2
comment: DASA-58 is an activator of tumour-associated pyruvate kinase M2 (PKM2) <Reference id=38487/>. PKM2 activation has potential to interfere with the anabolic metabolic pathway that is utilised by cancer cells to maintain high levels of proliferation. Like <Ligand id=10555/>, DASA-58 promotes formation of highly active PKM2 tetramers and suppresses tumour expansion in vivo <Reference id=38483/>.
iupac name: 3-[[4-(2,3-dihydro-1,4-benzodioxin-6-ylsulfonyl)-1,4-diazepan-1-yl]sulfonyl]aniline
xref: CHEMBL1089334
synonym: DASA58
synonym: ML203
synonym: ML-203
synonym: compound 1 [PMID: 21958545]
approved: f
ligand name: DASA-58
type: SyntheticOrganicLigand

TEPP-46
in ch i key: ZWKJWVSEDISQIS-UHFFFAOYSA-N
in ch i: InChI=1S/C17H16N4O2S2/c1-20-13-7-14(25(2)23)24-16(13)12-8-19-21(17(22)15(12)20)9-10-4-3-5-11(18)6-10/h3-8H,9,18H2,1-2H3
comment: TEPP-46 is an activator of tumour-associated pyruvate kinase M2 (PKM2) <Reference id=38483/><Reference id=38484/><Reference id=38485/>. It promotes formation of the highly active PKM2 tetramer, and reduces cancer cell proliferation by interfering with anabolic metabolism. It is active in a mouse xenograft model <Reference id=38484/>.
xref: CHEMBL1085588
synonym: TEPP46
synonym: ML265
synonym: ML-265
synonym: compound 46 [PMID: 20451379]
approved: f
ligand name: TEPP-46
type: SyntheticOrganicLigand

SKA-111
canonical SMILES: Nc1sc2c(n1)c1ccccc1c(c2)C
isomeric SMILES: Nc1sc2c(n1)c1ccccc1c(c2)C
in ch i key: JQZQMZXXJFFVFE-UHFFFAOYSA-N
in ch i: InChI=1S/C12H10N2S/c1-7-6-10-11(14-12(13)15-10)9-5-3-2-4-8(7)9/h2-6H,1H3,(H2,13,14)
comment: SKA-111 is a positive KCa channel gating modulator with selectivity for KCa3.1.
iupac name: 5-Methylnaphtho[1,2-d]thiazol-2-amine
synonym: SKA 111
synonym: SKA111
approved: f
ligand name: SKA-111
type: SyntheticOrganicLigand

elexacaftor
in ch i key: MVRHVFSOIWFBTE-INIZCTEOSA-N
comment: Elexacaftor (VX-445) is a next-generation CFTR corrector type agent. Like its predecessor <Ligand id=10199/>, elexacaftor is designed to improve CFTR protein processing and trafficking in the presence of the F508del mutation, although because its mechanism of action is different from that of tezacaftor, its functional effects appear to be additive <Reference id=38476/>. As such a triple combination therapeutic with tezacaftor, izacaftor (a CFTR potentiator that increases CFTR channel gating activity) and elexacaftor increases CFTR function beyond that achieved by current standard of care with tezacaftor/izacaftor, and improves clinical symptoms in patients with cystic fibrosis with one or two F508del alleles <Reference id=38477/>.
iupac name: N-(1,3-dimethylpyrazol-4-yl)sulfonyl-6-[3-(3,3,3-trifluoro-2,2-dimethylpropoxy)pyrazol-1-yl]-2-[(4S)-2,2,4-trimethylpyrrolidin-1-yl]pyridine-3-carboxamide
synonym: VX-445
synonym: Compound 1 [WO2018107100A1]
approved: t
ligand name: elexacaftor
type: SyntheticOrganicLigand

compound 18e [PMID: 31670517]
in ch i key: CVLXNRIQVFIVGY-UHFFFAOYSA-N
in ch i: InChI=1S/C25H34FN7O/c1-17(2)33-16-19(15-28-33)24-18(3)14-27-25(30-24)29-20-5-6-23(22(26)13-20)32-9-7-21(8-10-32)31(4)11-12-34/h5-6,13-17,21,34H,7-12H2,1-4H3,(H,27,29,30)
comment: Compound 18e is an optimised, orally bioavailable dual Janus kinase 2 (JAK2)/fms related tyrosine kinase 3 (FLT3) inhibitor <Reference id=38471/>. It exhibits anti-tumour activity in vitro and in vivo.
iupac name: 2-((1-(2-Fluoro-4-((4-(1-isopropyl-1H-pyrazol-4-yl)-5-methylpyrimidin-2-yl)amino)phenyl)piperidin-4-yl)(methyl)amino)ethan-1-ol
approved: f
ligand name: compound 18e [PMID: 31670517]
type: SyntheticOrganicLigand

compound 10 [PMID: 31663733]
in ch i key: ZSDQWZVUVIKSDR-YTTGMZPUSA-N
comment: Compound 10 is an irreversible inhibitor of the cholesterol pathway enzyme CYP51A1 <Reference id=38469/>. It was designed to validate the druggability of human CYP51A1, which had previously proven to be resistant to pharmacological inhibition. An X-ray structure of the compound 10/CYP51A1 complex has been deposited with the Protein Data Bank, PDB ID 6Q2T.
iupac name: (R)-N-(1-(3-Chloro-4′-fluoro-[1,1′-biphenyl]-4-yl)-2-(1H-imidazol-1-yl)ethyl)-4-(5-(3-fluoro-5-(5-fluoropyrimidin-4-yl)phenyl)-1,3,4-oxadiazol-2-yl)benzamide
approved: f
ligand name: compound 10 [PMID: 31663733]
type: SyntheticOrganicLigand

THAL-SNS-032
in ch i key: BXDZOYLPNAIDOC-UHFFFAOYSA-N
comment: THAL-SNS-032 is a cereblon (CRBN)-engaging degrader of the CDK9 kinase protein <Reference id=38467/>. It is a bifunctional molecule that uses PROTAC technology to promote degradation of the CDK9 protein. Degradation is achieved through co-engagement of CDK9 (via the multi-targeting kinase inhibitor <Ligand id=5670/>, a.k.a. SNS-032) and cereblon (via a <Ligand id=7327/> derivative) to promote E3 ligase-mediated ubiquitination and proteasomal degradation of CDK9.
synonym: THAL-SNS032
approved: f
ligand name: THAL-SNS-032
type: SyntheticOrganicLigand

dBRD9-A
in ch i key: ZDINQSNMYRVAGP-UHFFFAOYSA-N
in ch i: InChI=1S/C42H49N7O8/c1-47(23-31-34(56-3)20-26(21-35(31)57-4)30-24-48(2)40(53)29-22-43-19-16-27(29)30)25-37(51)45-18-10-8-6-5-7-9-17-44-32-13-11-12-28-38(32)42(55)49(41(28)54)33-14-15-36(50)46-39(33)52/h11-13,16,19-22,24,33,44H,5-10,14-15,17-18,23,25H2,1-4H3,(H,45,51)(H,46,50,52)
comment: This is an analogue of <Ligand id=10545/>, that was designed to achieve enhanced BRD9 degradation properties <Reference id=38466/>. Like dBRD9 it is a PROTAC (proteolysis targeting chimera). dBRD9-A is a hybrid molecule that simultaneously engages the BRD9 bromodomain and recruits E3 ligase CRL4CRBN (using a <Ligand id=7348/>-based module) to target BRD9 for destruction via E3 ligase-mediated ubiquitination and proteasomal degradation.
iupac name: 2-[[2,6-dimethoxy-4-(2-methyl-1-oxo-2,7-naphthyridin-4-yl)phenyl]methyl-methylamino]-N-[8-[[2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-4-yl]amino]octyl]acetamide
approved: f
ligand name: dBRD9-A
type: SyntheticOrganicLigand

dBRD9
in ch i key: AIOCFZJGGGEWDK-UHFFFAOYSA-N
in ch i: InChI=1S/C40H45N7O10/c1-45(21-29-32(54-3)18-24(19-33(29)55-4)28-22-46(2)38(51)27-20-41-11-10-25(27)28)23-35(49)43-13-15-57-17-16-56-14-12-42-30-7-5-6-26-36(30)40(53)47(39(26)52)31-8-9-34(48)44-37(31)50/h5-7,10-11,18-20,22,31,42H,8-9,12-17,21,23H2,1-4H3,(H,43,49)(H,44,48,50)
comment: dBRD9 is a targeted BRD9 degrader molecule <Reference id=38465/>. It is a bifunctional molecule that simultaneously engages the BRD9 bromodomain and cereblon (CRBN; a component of the E3 ubiquitin ligase complex) to trigger BRD9 ubiquitination and proteasomal degradation. Such molecules can be described as PROTACs (proteolysis targeting chimeras). Cereblon engagement is mediated by the probe's <Ligand id=7348/> module, and BRD9 recruitment is achieved by an optimised BRD9 ligand. dBRD9 is suitable as a tool/probe to interrogate BRD9's biological role and therapeutic potential.
iupac name: 2-[[2,6-dimethoxy-4-(2-methyl-1-oxo-2,7-naphthyridin-4-yl)phenyl]methyl-methylamino]-N-[2-[2-[2-[[2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-4-yl]amino]ethoxy]ethoxy]ethyl]acetamide
synonym: Naphthiridinone degrader 6
approved: f
ligand name: dBRD9
type: SyntheticOrganicLigand

QC-01-175
in ch i key: NWTCZTAQSRLSCP-UHFFFAOYSA-N
in ch i: InChI=1S/C33H34N6O7/c40-28(8-5-20-4-6-21-23-19-34-11-10-24(23)37-26(21)18-20)36-13-15-46-17-16-45-14-12-35-25-3-1-2-22-30(25)33(44)39(32(22)43)27-7-9-29(41)38-31(27)42/h1-4,6,10-11,18-19,27,35,37H,5,7-9,12-17H2,(H,36,40)(H,38,41,42)
comment: QC-01-175 is a functional degrader of pathogenic tau protein <Reference id=38464/>. It is a bifunctional molecule that simultaneously engages tau and cereblon (CRBN; a component of the E3 ubiquitin ligase complex) to trigger tau ubiquitination and proteasomal degradation. Such molecules can be described as PROTACs (proteolysis targeting chimeras). Cereblon engagement is mediated by the probe's <Ligand id=7348/> module, and tau recruitment is achieved by a variant of the tau PET tracer T807 (<Ligand id=9100/>). QC-01-175 retains the tau ligand-binding capacity of the parent T807, but with reduced off-target MAO inhibition liability.
approved: f
ligand name: QC-01-175
type: SyntheticOrganicLigand

MK6-83
canonical SMILES: Cc1ccc(s1)S(=O)(=O)Nc1ccccc1N1CCCCC1
isomeric SMILES: Cc1ccc(s1)S(=O)(=O)Nc1ccccc1N1CCCCC1
in ch i key: IRGYSXZCDAWOOC-UHFFFAOYSA-N
in ch i: InChI=1S/C16H20N2O2S2/c1-13-9-10-16(21-13)22(19,20)17-14-7-3-4-8-15(14)18-11-5-2-6-12-18/h3-4,7-10,17H,2,5-6,11-12H2,1H3
comment: Potent TRPML1 channel activator
iupac name: 5-methyl-N-(2-piperidin-1-ylphenyl)thiophene-2-sulfonamide
approved: f
ligand name: MK6-83
type: SyntheticOrganicLigand

MAK683
in ch i key: XLIBABIFOBYHSV-UHFFFAOYSA-N
in ch i: InChI=1S/C20H17FN6O/c1-12-13(3-2-7-22-12)16-10-24-20(27-11-25-26-19(16)27)23-9-15-14-6-8-28-18(14)5-4-17(15)21/h2-5,7,10-11H,6,8-9H2,1H3,(H,23,24)
comment: MAK683 is an allosteric inhibitor of the protein-protein interaction (PPI) between embryonic ectoderm development protein (EED) and polycomb repressive complex 2 (PRC2; EZH2) that was developped by Novartis for potential antineoplastic activity. It is one of the chemical structures claimed in Novartis' patent WO2016103155A1, and it targets EED <Reference id=38381/>. EED has no intrinsic enzymatic activity but it is essential for PRC2 function. EED binds to histone H3K27 trimethylation marks which localizes the PRC2 complex to the chromatin substrate and allosterically activates PRC2's methyltransferase activity. Disruption of the EED-EZH2 PPI results in a loss of H3K27me3-stimulated PRC2 activity and reduces histone H3K27 trimethylation. In EZH2-mutated and PRC2-dependent cancer cells this PPI disruption modifies gene expression patterns within cancer pathways and ultimately decreases tumour cell proliferation.
iupac name: N-[(5-fluoro-2,3-dihydro-1-benzofuran-4-yl)methyl]-8-(2-methylpyridin-3-yl)-[1,2,4]triazolo[4,3-c]pyrimidin-5-amine
synonym: MAK-683
synonym: EED inhibitor-1
synonym: example 2 [WO2016103155A1]
approved: f
ligand name: MAK683
type: SyntheticOrganicLigand

CLUL1 (52-77)
in ch i key: RVUJAIDUVQKVDU-OTFOMDLSSA-N
comment: This is a 26 amino acid peptide derived from the human clusterin-like protein 1 (CLUL1). It is amino acids 52-77 using Uniprot numbering. It has been identified as a novel ligand for the GPCR, GPR55 <Reference id=38463/>.
approved: f
ligand name: CLUL1 (52-77)
type: PeptideLigand

levosalbutamol
canonical SMILES: OCc1cc(ccc1O)C(CNC(C)(C)C)O
isomeric SMILES: OCc1cc(ccc1O)[C@H](CNC(C)(C)C)O
in ch i key: NDAUXUAQIAJITI-LBPRGKRZSA-N
in ch i: InChI=1S/C13H21NO3/c1-13(2,3)14-7-12(17)9-4-5-11(16)10(6-9)8-15/h4-6,12,14-17H,7-8H2,1-3H3/t12-/m0/s1
comment: Levosalbutamol is a short-acting β2-adrenoceptor agonist used in anti-asthma medications. Structurally it is the R enantiomer of the racemic mixture that has the INN <Ligand id=558/>. Levosalbutamol belongs to the 'short-acting beta-agonist' (SABA) drug family.
iupac name: 4-[(1R)-2-(tert-butylamino)-1-hydroxyethyl]-2-(hydroxymethyl)phenol
xref: CHEMBL1002
synonym: (R)-salbutamol
synonym: (-)-salbutamol
synonym: levalbuterol
synonym: (-)-albuterol
synonym: Xopenex®
approved: t
ligand name: levosalbutamol
type: SyntheticOrganicLigand

SPAG11B (61-103)
in ch i key: NZRXPCZWIFPFBB-SZWZVGMQSA-N
comment: This is a 43 amino acid peptide derived from the human sperm-associated antigen 11B (SPAG11B) protein precursor. It is amino acids 61-103 using Uniprot numbering. It has been identified as a novel ligand for the GPCR, GPR55 <Reference id=38463/>.
approved: f
ligand name: SPAG11B (61-103)
type: PeptideLigand

MSMB (91-114)
in ch i key: JXASPFJVDIPKEB-XNSPQFCGSA-N
comment: This is a 24 amino acid peptide derived from human microseminoprotein beta (MSMB protein). It is amino acids 91-114 using Uniprot numbering, and the carboxy-terminal 24 amino acids of the MSMB protein. It has been identified as a novel ligand for the GPCR, GPR55 <Reference id=38463/>.
approved: f
ligand name: MSMB (91-114)
type: PeptideLigand

Chgb (511-532)
in ch i key: USZLWOIXWADXRT-HXRUCQLXSA-N
comment: This is a 22 amino acid peptide derived from the rat secretogranin-1 protein. It is amino acids 511-532 using Uniprot numbering. It has been identified as a novel ligand for the GPCR, GPR55 <Reference id=38463/>.
approved: f
ligand name: Chgb (511-532)
type: PeptideLigand

MANSC (415-431)
in ch i key: CCMVMLBWJFAFRO-IAMXVIFYSA-N
comment: This is a 17 amino acid peptide derived from the human MANSC domain-containing protein 1 (MANSC1 protein). It is amino acids 415-431 using Uniprot numbering, and the carboxy-terminal 17 amino acids of the MANSC1 protein. It has been identified as a novel ligand for the GPCR, GPR55 <Reference id=38463/>.
approved: f
ligand name: MANSC (415-431)
type: PeptideLigand

3β-OH
canonical SMILES: N#CC1CCC2C1(C)CCC1C2CCC2C1(C)CCC(C2)O
in ch i key: DVTDUTYENPZLFP-FXEFULGUSA-N
in ch i: InChI=1S/C20H31NO/c1-19-9-7-15(22)11-13(19)3-5-16-17-6-4-14(12-21)20(17,2)10-8-18(16)19/h13-18,22H,3-11H2,1-2H3/t13-,14-,15+,16?,17?,18?,19+,20-/m1/s1
comment: 3β-OH is a neuroactive steroid analogue that produces general anaesthetic/hypnotic effects in vivo, but without associated neurotoxicity <Reference id=38456/>. It blocks presynaptic transmitter release without affecting major postsynaptic ligand-gated ion channels. The chemical structure of 3β-OH is based on that of progesterone, with an OH substitution at position 3, and a CN group substitution at position 3. This chemical structure is claimed as B260 in patent WO2015149066A1 <Reference id=38457/>. Mechanistically, 3β-OH selectively targets T-type voltage-gated calcium channels (T-channels; Cav3.1, Cav3.2, and Cav3.3) to mediate its hypnotic activity. 3β-OH exhibits minimal activity towards voltage-gated Na+ and K+ currents, N-type and L-type Ca2+ currents <Reference id=38458/><Reference id=38459/> or currents generated via recombinant GABAA and NMDA channels <Reference id=38460/>.
iupac name: (3S,5R,10S,13S,17S)-3-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-17-carbonitrile
synonym: (3β,5β,17β)-3-hydroxyandrostane-17-carbonitrile
synonym: B260
approved: f
ligand name: 3β-OH
type: SyntheticOrganicLigand

dTRIM24
in ch i key: QUQTXFIMYFMULC-OGOZKGDESA-N
comment: dTRIM24 is a Von Hippel-Lindau (VHL)-engaging degrader of the chromatin modifying enzyme TRIM24 <Reference id=38455/>. It is a hybrid molecule of a TRIM24-engaging ligand (derived from ACS-9571) and a VHL-engaging ligand (VL-269). dTRIM24 more effectively displaces TRIM24 from chromatin compared to the parent TRIM24 bromodomain binding ligand IACS-9571.
approved: f
ligand name: dTRIM24
type: SyntheticOrganicLigand

thiamet-G
canonical SMILES: OCC1OC2SC(=NCC)NC2C(C1O)O
in ch i key: PPAIMZHKIXDJRN-FMDGEEDCSA-N
in ch i: InChI=1S/C9H16N2O4S/c1-2-10-9-11-5-7(14)6(13)4(3-12)15-8(5)16-9/h4-8,12-14H,2-3H2,1H3,(H,10,11)/t4-,5-,6-,7-,8-/m1/s1
comment: Thiamet-G is a O-GlcNAcase inhibitor and is widely used as a pharmacological tool to investigate the role of O-GlcNAcase (and its potential for modulation) in tau-related dementias <Reference id=38341/>. It has been used as a lead scaffold for the development of O-GlcNAcase inhibitors that are optimised for clinical utility, such as <Ligand id=10508/> <Reference id=38338/>.
iupac name: (3aR,5R,6S,7R,7aR)-2-ethylimino-5-(hydroxymethyl)-1,3a,5,6,7,7a-hexahydropyrano[3,2-d][1,3]thiazole-6,7-diol
xref: CHEMBL1213603
synonym: thiamet G
approved: f
ligand name: thiamet-G
type: SyntheticOrganicLigand

DD-03-171
in ch i key: QBPVFCNYKUENHU-UHFFFAOYSA-N
in ch i: InChI=1S/C55H62N10O8/c1-34-39(12-10-14-41(34)60-49(68)35-16-20-37(21-17-35)55(2,3)4)43-33-62(5)54(73)48(59-43)58-38-22-18-36(19-23-38)51(70)64-30-28-63(29-31-64)27-9-7-6-8-26-56-46(67)32-57-42-15-11-13-40-47(42)53(72)65(52(40)71)44-24-25-45(66)61-50(44)69/h10-23,33,44,57H,6-9,24-32H2,1-5H3,(H,56,67)(H,58,59)(H,60,68)(H,61,66,69)
comment: DD-03-171 is a cereblon (CRBN)-engaging degrader (or PROTAC; proteolysis targeting chimera) of BTK protein <Reference id=38454/>. The BTK inhibitor portion of DD-03-171 is derived from <Ligand id=8066/>, and this is conjugated to <Ligand id=7327/> using a saturated hydrocarbon linker to create the hybrid molecule. DD-03-171 produces potent antiproliferative effects on lymphoma cells in vitro and on patient-derived xenografts in vivo. It is suggested that DD-03-171's mechanism of action may be able to overcome tumour resistance to <Ligand id=6912/> therapy.
iupac name: 4-tert-butyl-N-[3-[6-[4-[4-[6-[[2-[[2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-4-yl]amino]acetyl]amino]hexyl]piperazine-1-carbonyl]anilino]-4-methyl-5-oxopyrazin-2-yl]-2-methylphenyl]benzamide
approved: f
ligand name: DD-03-171
type: SyntheticOrganicLigand

dBET6
in ch i key: JGQPZPLJOBHHBK-UFXYQILXSA-N
comment: dBET6 is a BRD4-targeting, cereblon (CRBN)-engaging degrader (or PROTAC; proteolysis targeting chimera) <Reference id=38453/>.
approved: f
ligand name: dBET6
type: SyntheticOrganicLigand

dTAG-13
in ch i key: BJFBRLAWLPZOMJ-QHVFGHLPSA-N
in ch i: InChI=1S/C57H68N4O15/c1-7-37(36-32-47(71-4)52(73-6)48(33-36)72-5)54(65)60-29-14-12-19-41(60)57(68)76-43(25-22-35-23-26-44(69-2)46(31-35)70-3)38-17-10-11-20-42(38)75-34-50(63)58-28-13-8-9-15-30-74-45-21-16-18-39-51(45)56(67)61(55(39)66)40-24-27-49(62)59-53(40)64/h10-11,16-18,20-21,23,26,31-33,37,40-41,43H,7-9,12-15,19,22,24-25,27-30,34H2,1-6H3,(H,58,63)(H,59,62,64)/t37-,40?,41-,43+/m0/s1
comment: dTAG-13 is a PROTAC (proteolysis targeting chimera) <Reference id=38452/>. It is a hybrid molecule that simultaneously binds FKBP12F36V chimeric proteins and recruits E3 ligase CRL4CRBN to target the defective proteins for destruction via E3 ligase-mediated ubiquitination and proteasomal degradation.
iupac name: [(1R)-3-(3,4-dimethoxyphenyl)-1-[2-[2-[6-[2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-4-yl]oxyhexylamino]-2-oxoethoxy]phenyl]propyl] (2S)-1-[(2S)-2-(3,4,5-trimethoxyphenyl)butanoyl]piperidine-2-carboxylate
approved: f
ligand name: dTAG-13
type: SyntheticOrganicLigand

BSJ-03-123
in ch i key: LUHCYAOYQIFNRN-UHFFFAOYSA-N
in ch i: InChI=1S/C47H56N10O11/c1-29-34-27-50-47(53-42(34)56(31-6-3-4-7-31)45(63)40(29)30(2)58)51-37-12-10-32(26-49-37)55-17-15-54(16-18-55)19-21-66-23-25-67-24-22-65-20-14-48-39(60)28-68-36-9-5-8-33-41(36)46(64)57(44(33)62)35-11-13-38(59)52-43(35)61/h5,8-10,12,26-27,31,35H,3-4,6-7,11,13-25,28H2,1-2H3,(H,48,60)(H,52,59,61)(H,49,50,51,53)
comment: BSJ-03-123 is a PROTAC (proteolysis targeting chimera) <Reference id=38451/>. It is a hybrid molecule that simultaneously inhibits CDK4/CDK6 kinase activity and recruits E3 ligase CRL4CRBN to target the kinases for destruction via E3 ligase-mediated ubiquitination and proteasomal degradation. BSJ-03-123 is a <Ligand id=7380/>-based selective CDK6 degrader.
iupac name: N-[2-[2-[2-[2-[4-[6-[(6-acetyl-8-cyclopentyl-5-methyl-7-oxopyrido[2,3-d]pyrimidin-2-yl)amino]pyridin-3-yl]piperazin-1-yl]ethoxy]ethoxy]ethoxy]ethyl]-2-[2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-4-yl]oxyacetamide
approved: f
ligand name: BSJ-03-123
type: SyntheticOrganicLigand

BSJ-04-132
in ch i key: GWLSXEHHNOBFOI-UHFFFAOYSA-N
in ch i: InChI=1S/C42H49N11O7/c1-49(2)40(58)31-22-26-23-45-42(48-37(26)52(31)27-8-3-4-9-27)46-33-14-12-28(24-44-33)51-20-18-50(19-21-51)17-6-5-16-43-35(55)25-60-32-11-7-10-29-36(32)41(59)53(39(29)57)30-13-15-34(54)47-38(30)56/h7,10-12,14,22-24,27,30H,3-6,8-9,13,15-21,25H2,1-2H3,(H,43,55)(H,47,54,56)(H,44,45,46,48)
comment: BSJ-04-132 is a PROTAC (proteolysis targeting chimera) <Reference id=38451/>. It is a hybrid molecule that simultaneously inhibits CDK4/CDK6 kinase activity and recruits E3 ligase CRL4CRBN to target kinase protein destruction via E3 ligase-mediated ubiquitination and proteasomal degradation. BSJ-04-132 is a <Ligand id=7383/>-based degrader that selectively degrades CDK4.
iupac name: 7-Cyclopentyl-2-[[5-[4-[4-[2-[[2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindolin-4-yl]oxy]acetamido]butyl]piperazin-1-yl]pyridin-2-yl]amino]-N,N-dimethyl-7H-pyrrolo[2,3d]pyrimidine-6-carboxamide
approved: f
ligand name: BSJ-04-132
type: SyntheticOrganicLigand

BSJ-03-204
in ch i key: KDMOCOWXLQOXEB-UHFFFAOYSA-N
in ch i: InChI=1S/C43H48N10O8/c1-25-30-23-46-43(49-38(30)52(27-8-3-4-9-27)41(59)36(25)26(2)54)47-33-14-12-28(22-45-33)51-20-18-50(19-21-51)17-6-5-16-44-35(56)24-61-32-11-7-10-29-37(32)42(60)53(40(29)58)31-13-15-34(55)48-39(31)57/h7,10-12,14,22-23,27,31H,3-6,8-9,13,15-21,24H2,1-2H3,(H,44,56)(H,48,55,57)(H,45,46,47,49)
comment: BSJ-03-204 is a PROTAC (proteolysis targeting chimera) <Reference id=38451/>. It is a hybrid molecule that simultaneously inhibits CDK4/CDK6 kinase activity and recruits E3 ligase CRL4CRBN to target these kinases for destruction via E3 ligase-mediated ubiquitination and proteasomal degradation. The CDK4/CDK6 inhibitor <Ligand id=7380/> is linked to an imide-based cereblon ligand via a linker molecule. BSJ-03-204 has an oxylamide in place of the thalidomide aryl amine nitrogen, and this blocks degradation of IKZF1 and IKZF3 (which are known targets of imides and some imide‐based degraders).
approved: f
ligand name: BSJ-03-204
type: SyntheticOrganicLigand

FzM1
in ch i key: OBTSACXGWYGCPK-UHFFFAOYSA-N
in ch i: InChI=1S/C21H16N2O2S/c24-19-12-16(20-6-3-9-26-20)11-18(13-19)23-21(25)22-17-8-7-14-4-1-2-5-15(14)10-17/h1-13,24H,(H2,22,23,25)
comment: FzM1 is a negative allosteric modulator of FZD4 <Reference id=37407/><Reference id=37406/>.
iupac name: 3-[3-hydroxy-5-(thiophen-2-yl)phenyl]-1-(naphthalen-2-yl)urea
approved: f
ligand name: FzM1
type: SyntheticOrganicLigand

setogepram
canonical SMILES: CCCCCc1cccc(c1)CC(=O)O
isomeric SMILES: CCCCCc1cccc(c1)CC(=O)O
in ch i key: PEGQOIGYZLJMIB-UHFFFAOYSA-N
in ch i: InChI=1S/C13H18O2/c1-2-3-4-6-11-7-5-8-12(9-11)10-13(14)15/h5,7-9H,2-4,6,10H2,1H3,(H,14,15)
comment: Setogepram (PBI-4050) is an orally active, synthetic analogue of a medium-chain fatty acid that displays agonist and antagonist ligand affinity toward GPR40 and GPR84, respectively <Reference id=35957/>. it is a potentially novel first-in-class compound with significant antifibrotic and antiinflammatory activities that was being developed by Liminal BioSciences (formerly Prometic Life Sciences).
iupac name: 2-(3-pentylphenyl)acetic acid
synonym: PBI4050
synonym: PBI 4050
synonym: 3-pentylbenzeneacetic acid
synonym: PBI-4050
synonym: fezagepras
approved: f
ligand name: setogepram
type: SyntheticOrganicLigand

TL13-112
in ch i key: XIRQUXILNXIWDI-UHFFFAOYSA-N
comment: TL13-112 is a PROTAC (proteolysis targeting chimera) <Reference id=38450/>. It is a hybrid molecule that simultaneously inhibits ALK kinase activity and recruits E3 ligase CRL4CRBN to target ALK for destruction via E3 ligase-mediated ubiquitination and proteasomal degradation. The ALK targeting function is based on the ALK inhibitor <Ligand id=5714/>, and the cereblon ligand component is derived from <Ligand id=7348/>.
iupac name: N-[2-[2-[2-[4-[4-[[5-chloro-4-(2-propan-2-ylsulfonylanilino)pyrimidin-2-yl]amino]-2-methyl-5-propan-2-yloxyphenyl]piperidin-1-yl]ethoxy]ethoxy]ethyl]-2-[[2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-4-yl]amino]acetamide
approved: f
ligand name: TL13-112
type: SyntheticOrganicLigand

compound 32 [PMID: 31638797]
in ch i key: ONXFNBOZJKXCNC-ZJSXRUAMSA-N
comment: Compound 32 is reported as a potent and selective inverse agonist of RORγt <Reference id=38448/>. It exhibits in vivo activity. Compound 32 is one of the tricyclic sulfone RORγ modulators claimed in Bristol-Myers Squibb's patent WO2016179460A1 <Reference id=38449/>.
iupac name: [(3aR,9bR)-9b-(4-fluorophenyl)sulfonyl-7-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-2,3a,4,5-tetrahydro-1H-benzo[e]indol-3-yl]-(4-hydroxy-1,1-dioxothian-4-yl)methanone
synonym: example 69 [WO2016179460A1]
approved: f
ligand name: compound 32 [PMID: 31638797]
type: SyntheticOrganicLigand

LASW1393
in ch i key: NIIBPFADTOPKBI-HAQNSBGRSA-N
in ch i: InChI=1S/C18H19N7O2/c19-8-7-11-3-5-12(6-4-11)25-15-14(23-18(25)27)10-21-17(24-15)22-13-2-1-9-20-16(13)26/h1-2,9-12H,3-7H2,(H,20,26)(H,23,27)(H,21,22,24)/t11-,12-
comment: LASW1393 is a pan-JAK inhibitor that was developed as an inhalation anti-inflammatory <Reference id=38440/>. It is active in vivo in a rat model of airway inflammation. PubChem CID 71062030 represents the compound without specified stereochemistry.
iupac name: 2-[(1r,4r)-4-{8-oxo-2-[(2-oxo-1,2-dihydropyridin-3-yl)amino]-8,9-dihydro-7H-purin-9-yl}cyclohexyl]acetonitrile
synonym: compound 34 [PMID: 31609613]
synonym: LASW-1393
approved: f
ligand name: LASW1393
type: SyntheticOrganicLigand

SIAIS178
in ch i key: YGQREOJIRFCRKQ-ZIBKGDFVSA-N
comment: SIAIS178 is a novel proteolysis-targeting chimeric (PROTAC) degrader <Reference id=38439/>. It is a hybrid molecule that connects the BCR-ABL kinase inhibitor <Ligand id=5678/> to a ligand for Von Hippel-Lindau (VHL) E3 ubiquitin ligase via an optimised linker. SIAIS178 targets BCR-ABL protein for VHL-mediated degradation. The hybrid molecule exhibits an improved kinase selectivity profile compared to dasatinib (in a KINOME Scan evaluation). An epimer of SIAIS178 with a reversed (S) configuration at the proline 4-position of the VHL ligand does not bind to the VHL ligase and is inactive with respect to BCR-ABL degradation.
iupac name: N-(2-Chloro-6-methylphenyl)-2-((6-(4-(8-(((S)-1-((2S,4R)-4-hydroxy-2-((4-(4-methyl-thiazol-5-yl)benzyl)carbamoyl)pyrrolidin-1-yl)-3,3-dimethyl-1-oxobutan-2-yl)amino)-8-oxooctanoyl)piperazin-1-yl)-2-methylpyrimidin-4-yl)amino)thiazole-5-carboxamide
synonym: compound 19 [PMID: 31539241]
synonym: SIAIS-178
approved: f
ligand name: SIAIS178
type: SyntheticOrganicLigand

diroximel fumarate
canonical SMILES: COC(=O)C=CC(=O)OCCN1C(=O)CCC1=O
isomeric SMILES: COC(=O)/C=C/C(=O)OCCN1C(=O)CCC1=O
in ch i key: YIMYDTCOUQIDMT-SNAWJCMRSA-N
in ch i: InChI=1S/C11H13NO6/c1-17-10(15)4-5-11(16)18-7-6-12-8(13)2-3-9(12)14/h4-5H,2-3,6-7H2,1H3/b5-4+
comment: Diroximel fumarate is a novel oral fumarate prodrug. It is rapidly converted to monomethyl fumarate, which is the same active metabolite of <Ligand id=7045/>.
iupac name: 4-O-[2-(2,5-dioxopyrrolidin-1-yl)ethyl] 1-O-methyl (E)-but-2-enedioate
xref: CHEMBL3989944
synonym: BIIB098
synonym: ALKS8700
synonym: ALKS-8700
synonym: Vumerity®
approved: t
ligand name: diroximel fumarate
type: SyntheticOrganicLigand

MW150
in ch i key: CIIVUDIZZJLXCN-UHFFFAOYSA-N
in ch i: InChI=1S/C24H23N5/c1-28-12-14-29(15-13-28)23-17-22(19-8-10-25-11-9-19)24(27-26-23)21-7-6-18-4-2-3-5-20(18)16-21/h2-11,16-17H,12-15H2,1H3
comment: MW150 is a novel, pharmacologically selective p38α MAP kinase (MAPK14) inhibitor <Reference id=38428/><Reference id=38426/>. It is CNS-penetrant and is being pursued as a clinical lead for neurological disorders. MW150 is claimed in patent WO2014145485A2 that was filed by The Trustees Of Columbia University In The City Of New York <Reference id=38430/>.
iupac name: 6-(4-methylpiperazin-1-yl)-3-naphthalen-2-yl-4-pyridin-4-ylpyridazine
synonym: MW01-18-150SRM
synonym: compound 11 [PMID: 30978288]
synonym: MW-150
synonym: compound 8 [PMID: 25676389]
synonym: compound 27 [WO2014145485A2]
approved: f
ligand name: MW150
type: SyntheticOrganicLigand

compound 7f [PMID: 31251063]
canonical SMILES: O=C(NC1CC(=O)NC1=O)C=Cc1ccccc1
isomeric SMILES: O=C(NC1CC(=O)NC1=O)/C=C/c1ccccc1
in ch i key: NSEUGMATEWSNTO-VOTSOKGWSA-N
in ch i: InChI=1S/C13H12N2O3/c16-11(7-6-9-4-2-1-3-5-9)14-10-8-12(17)15-13(10)18/h1-7,10H,8H2,(H,14,16)(H,15,17,18)/b7-6+
comment: Compound 7f is a cereblon-targeting compound with immunomodulatory potential <Reference id=38424/>. It promotes proteasomal degradation of the lymphoid transcription factor neo-substrate Aiolos (IKZF3), but utilises a recognition mode that is distinct from that of the classical thalidomide-based immunomodulatory drugs (IMiDs). 7f contains a cinnamamide group in place of the glutarimide moeity found in thalidomide IMiDs <Reference id=38424/>.
iupac name: N-(2,5-Dioxopyrrolidin-3-yl)cinnamamide
approved: f
ligand name: compound 7f [PMID: 31251063]
type: SyntheticOrganicLigand

avadomide
in ch i key: RSNPAKAFCAAMBH-UHFFFAOYSA-N
in ch i: InChI=1S/C14H14N4O3/c1-7-16-9-4-2-3-8(15)12(9)14(21)18(7)10-5-6-11(19)17-13(10)20/h2-4,10H,5-6,15H2,1H3,(H,17,19,20)
comment: Avadomide (CC-122) is a cereblon (CRBN)-targeting compound <Reference id=38420/> that exhibits potent single-agent clinical antitumour and immunomodulatory activities <Reference id=38418/>. It retains the glutarimide moiety that is shared by all thalidomide family drugs, and which is known to directly interact with CRBN. The INN record specifies avadomide as a racemic mixture of enantiomers. We show the structure without specified stereochemistry to represent the mixture. It is claimed as Compound A in Celgene's patent WO2014039960A1 <Reference id=38419/>.
iupac name: 3-(5-amino-2-methyl-4-oxoquinazolin-3-yl)piperidine-2,6-dione
xref: CHEMBL3989934
synonym: CC-122
synonym: CC122
synonym: Compound A [WO2014039960A1]
approved: f
ligand name: avadomide
type: SyntheticOrganicLigand

MRI-1867
isomeric SMILES: Clc1ccc(cc1)C1=NN(C[C@@H]1c1ccccc1)/C(=N/S(=O)(=O)c1ccc(cc1)Cl)/N=C(/N)/C
in ch i key: GZPQTZIUWCQXCF-JOCHJYFZSA-N
comment: MRI-1867 is a hybrid molecule that acts both as an inverse agonist of peripheral cannabinoid receptor 1 (CB1) and as an inhibitor of inducible nitric oxide synthase (iNOS) <Reference id=38411/>. It is orally active, and the (S)-enantiomer is the more active form of the molecule. MRI-1867 was initially shown to exhibit anti-fibrotic activity in mouse models of liver fibrosis <Reference id=38411/> and it has subsequently been demonstrated to reduce signs of inflammation, fibrosis, oxidative stress and overall renal injury in a mouse model of obesity-induced chronic kidney disease <Reference id=38410/>. The therapeutic effect of MRI-1867 is two-fold; it both reduces fibrotic progression and is able to attenuate established fibrosis. Activities at both of its molecular targets are involved in mediating its in vivo efficacy.
iupac name: (4S)-N-(1-aminoethylidene)-5-(4-chlorophenyl)-N'-(4-chlorophenyl)sulfonyl-4-phenyl-3,4-dihydropyrazole-2-carboximidamide
synonym: MRI1867
synonym: (-)-MRI-1867
approved: f
ligand name: MRI-1867
type: SyntheticOrganicLigand

AM-6494
in ch i key: IPUJINDWAGRAHN-KNXBSLHKSA-N
comment: AM-6494 is a beta-secretase 1 (BACE1) inhibitor that has been demonstrated oral efficacy in reducing central Aβ40 load in in vivo models <Reference id=38408/>. It has been advanced to preclinical evaluation.
iupac name: N-[3-[(1S,5S,6S)-3-amino-1-(methoxymethyl)-5-methyl-2-thia-4-azabicyclo[4.1.0]hept-3-en-5-yl]-4,5-difluorophenyl]-5-prop-2-ynoxypyrazine-2-carboxamide
synonym: compound 20 [PMID: 31589043]
approved: f
ligand name: AM-6494
type: SyntheticOrganicLigand

NF-56-EJ40
in ch i key: UTWXDNZWMQAUKL-UHFFFAOYSA-N
in ch i: InChI=1S/C27H29N3O3/c1-29-13-15-30(16-14-29)19-20-9-11-21(12-10-20)22-6-4-7-24(17-22)27(33)28-25-8-3-2-5-23(25)18-26(31)32/h2-12,17H,13-16,18-19H2,1H3,(H,28,33)(H,31,32)
comment: NF-56-EJ40 is a potent succinate receptor antagonist <Reference id=38400/>.
approved: f
ligand name: NF-56-EJ40
type: SyntheticOrganicLigand

bilorphin
in ch i key: IYNDNOATOVLHNV-POTDNYQPSA-N
in ch i: InChI=1S/C30H43N5O5/c1-16(2)25(29(39)33-24(27(32)37)14-20-10-8-7-9-11-20)35-30(40)26(17(3)4)34-28(38)23(31)15-22-18(5)12-21(36)13-19(22)6/h7-13,16-17,23-26,36H,14-15,31H2,1-6H3,(H2,32,37)(H,33,39)(H,34,38)(H,35,40)/t23-,24-,25-,26+/m1/s1
comment: Bilorphin is a derivative of a naturally ocurring tetrapeptide that was isolated from an Australian estuarine isolate of Penicillium species MST-MF667 <Reference id=38388/>. It acts as a G protein signalling biased agonist of the μ-opioid receptor in vitro. Bilorphin promotes minimal β-arrestin recruitment and receptor internalization. Systemic and oral activity was achieved by glycosylating the C-terminal residue of bilorphin to create bilactorphin. The in vivo analgesic potency of bilactorphin is similar to that of morphine.
synonym: peptide 3c [PMID: 31611414]
approved: f
ligand name: bilorphin
type: SyntheticOrganicLigand

CB-103
canonical SMILES: Nc1ccc(nc1)Oc1ccc(cc1)C(C)(C)C
isomeric SMILES: Nc1ccc(nc1)Oc1ccc(cc1)C(C)(C)C
in ch i key: WHIWGRCYMQLLAO-UHFFFAOYSA-N
in ch i: InChI=1S/C15H18N2O/c1-15(2,3)11-4-7-13(8-5-11)18-14-9-6-12(16)10-17-14/h4-10H,16H2,1-3H3
comment: CB-103 is a first-in-class, small-molecule, orally active, pan-NOTCH inhibitor that is being investigated for anti-cancer potential <Reference id=41448/><Reference id=41184/>. It is being developed by Cellestia. The CAS number provided within the full documentation for the study entitled 'A Phase I/IIA, Multi-Centre, Open-Label, Dose-Escalation Study with Expansion Arms to Assess the Safety, Tolerability, Pharmacokinetics and Preliminary Efficacy of CB-103 Administered Orally in Adult Patients with Advanced or Metastatic Solid Tumours and Haematological Malignancies Characterised by Alterations of the NOTCH Signalling Pathway' (EudraCT protocol 2017-001491-35) allowed us to identify a chemical structure for CB-103, frior to formal name>structure disclosure <Reference id=41448/>. Information disclosed in meeting abstract form suggests that CB-103 acts by inhibiting protein-protein interactions that are required to establish assembly of the functional NOTCH transcription complex in the nucleus. By acting at the most downstream point in the NOTCH pathway, CB-103 inhibits NOTCH signalling independently of the mechanisms of NOTCH activation. NOTCH pathway signalling, and the approaches being explored for therapeutic targeting are reviewed by Sorrentino et al., 2019 <Reference id=38384/>.
iupac name: 6-(4-tert-butylphenoxy)pyridin-3-amine
xref: CHEMBL1420319
synonym: CB103
approved: f
ligand name: CB-103
type: SyntheticOrganicLigand

GSK369796
in ch i key: ZVMMVSSEAMUNGI-UHFFFAOYSA-N
in ch i: InChI=1S/C20H22ClN3O/c1-20(2,3)23-12-13-4-6-15(11-19(13)25)24-17-8-9-22-18-10-14(21)5-7-16(17)18/h4-11,23,25H,12H2,1-3H3,(H,22,24)
comment: GSK369796 is a 4-aminoquinoline antimalarial compound that was synthesised using <Ligand id=10018/> as the template molecule <Reference id=35350/>. The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
iupac name: 2-[(tert-butylamino)methyl]-5-[(7-chloroquinolin-4-yl)amino]phenol
xref: CHEMBL147806
synonym: N-tert-Butyl isoquine
synonym: GSK-369796
synonym: GSK 369796
approved: f
ligand name: GSK369796
type: SyntheticOrganicLigand

carotegrast
in ch i key: YQKBOUPIOWUMTE-NRFANRHFSA-N
comment: Carotegrast (HCA2969) is the active metabolite of <Ligand id=10510/> <Reference id=38348/><Reference id=38517/>. It acts as an antagonist of α4 integrin-mediated transmigration of leukocytes to sites of inflammation. The chemical structure of carotegrast is claimed as example 108 in EA Pharma patent US20110065918A1 which claims phenylalanine derivatives as α4 integrin antagonists for use as clinical therapeutics <Reference id=38352/>.
iupac name: (2S)-2-[(2,6-dichlorobenzoyl)amino]-3-[4-[6-(dimethylamino)-1-methyl-2,4-dioxoquinazolin-3-yl]phenyl]propanoic acid
synonym: HCA2969
approved: f
ligand name: carotegrast
type: SyntheticOrganicLigand

MK-8719
canonical SMILES: CCNC1=NC2C(S1)OC(C(C2O)O)C(F)F
in ch i key: UDQTXCHQKHIQMH-KYGLGHNPSA-N
in ch i: InChI=1S/C9H14F2N2O3S/c1-2-12-9-13-3-4(14)5(15)6(7(10)11)16-8(3)17-9/h3-8,14-15H,2H2,1H3,(H,12,13)/t3-,4-,5+,6+,8-/m1/s1
comment: MK-8719 is an inhibitor of O-GlcNAcase (OGA) that is being investigated as a disease modifying strategy for neurodegenerative tauopathies (including Alzheimer's disease, Pick's disease and progressive supranuclear palsy) <Reference id=38338/>. Development of MK-8719 is the result of a partnership between Merck and Alectos Therapeutics. MK-8719 was designed using on the scaffold of the carbohydrate-based lead molecule <Ligand id=10509/> and used medicinal chemistry and SAR to improve on thiamet-G's less than favourable drug-like properties (e.g. potency, selectivity, CNS exposure and metabolic stability). The current status of OGA inhibitor development as a novel preventative mechanism in neurodegeneration and age-related memory impairment is reveiwed by Rudrawar and Ryan (2019) <Reference id=38447/>.
iupac name: (3aR,5S,6S,7R,7aR)-5-(difluoromethyl)-2-ethylimino-1,3a,5,6,7,7a-hexahydropyrano[3,2-d][1,3]thiazole-6,7-diol
xref: CHEMBL4111094
synonym: compound 42 [PMID: 31487175]
synonym: MK8719
approved: f
ligand name: MK-8719
type: SyntheticOrganicLigand

LY3154207
in ch i key: XHCSBQBBGNQINS-DOTOQJQBSA-N
in ch i: InChI=1S/C24H29Cl2NO3/c1-15-18-7-4-6-16(10-11-24(2,3)30)19(18)12-17(14-28)27(15)23(29)13-20-21(25)8-5-9-22(20)26/h4-9,15,17,28,30H,10-14H2,1-3H3/t15-,17+/m0/s1
comment: LY3154207 is a potent, selective and orally active dopamine D1 receptor positive allosteric modulator (PAM) <Reference id=38335/>. The allosteric binding site of LY3154207 has been determined to reside at the intracellular loop 2 (ICL2) region of the receptor. D1 PAMs are being developed to address the poor drug-like properties of selective orthosteric D1 agonists. In particular, LY3154207 does not induce tachyphylaxis in preclinical models, whereas orthosteric agonists do. LY3154207 exhibits pro-cognitive and motor-enhancing effects in vivo, and is being considered for potential utility in the treatment of neuropsychiatric disorders <Reference id=38336/>.
iupac name: 2-(2,6-dichlorophenyl)-1-[(1S,3R)-3-(hydroxymethyl)-5-(3-hydroxy-3-methylbutyl)-1-methyl-3,4-dihydro-1H-isoquinolin-2-yl]ethanone
xref: CHEMBL3421729
synonym: compound 3 [PMID: 31532644]
synonym: LY-3154207
approved: f
ligand name: LY3154207
type: SyntheticOrganicLigand

GSK1482160
canonical SMILES: CN1C(=O)CCC1C(=O)NCc1cccc(c1Cl)C(F)(F)F
in ch i key: BJEMSIVBBUBXMZ-JTQLQIEISA-N
comment: GSK1482160 is a P2X7 receptor antagonist <Reference id=38332/>. It is active in in vivo animal models of pain.
xref: CHEMBL1222883
synonym: compound 1b [PMID: 31525963]
synonym: GSK-1482160
synonym: compound 31 [PMID: 20673717]
approved: f
ligand name: GSK1482160
type: SyntheticOrganicLigand

GSK1370319A
canonical SMILES: O=C(C1CCC(=O)N1C)NCc1ccc(cc1Cl)Cl
isomeric SMILES: O=C([C@@H]1CCC(=O)N1C)NCc1ccc(cc1Cl)Cl
in ch i key: YMNOJCVLDDTECB-NSHDSACASA-N
comment: GSK1370319A is a P2X7 receptor antagonist <Reference id=38331/>.
iupac name: (2S)-N-[(2,4-dichlorophenyl)methyl]-1-methyl-5-oxopyrrolidine-2-carboxamide
xref: CHEMBL2218759
synonym: compound 1a [PMID: 31525963]
approved: f
ligand name: GSK1370319A
type: SyntheticOrganicLigand

compound 16i [PMID: 31525963]
canonical SMILES: O=C(C1CCC(=O)N1c1cccs1)NCc1ccc(cc1Cl)Cl
in ch i key: PCHSDJRKGJKOAG-ZDUSSCGKSA-N
comment: Compound 16i is a pyroglutamide-based antagonist of the P2X7 ligand-gated ion channel <Reference id=38331/>.
approved: f
ligand name: compound 16i [PMID: 31525963]
type: SyntheticOrganicLigand

compound 16 [PMID: 31525966]
in ch i key: ZYYGNLSPUWSHQW-UHFFFAOYSA-N
comment: Compound 16 inhibits the cytolytic pore-forming activity of the perforin 1 protein <Reference id=38322/>. It has been developed to ascertain whether perforin inhibition can prevent early rejection of mismatched grafts in donor stem cell transplant procedures, and thereby improve successful engraftment. The acting hypothesis is based on the recognition that the natural killer (NK) cells that drive graft rejection overwhelmingly use perforin to kill non-self targets <Reference id=38329/><Reference id=38330/>. In addition, as these NK cells are resistant to radio- and immuno-suppression, an alternative mechanism is needed to limit their activity and to achieve clinical efficacy.
approved: f
ligand name: compound 16 [PMID: 31525966]
type: SyntheticOrganicLigand

NiK-21273
in ch i key: YEDOPHDWRSVQOP-UHFFFAOYSA-N
comment: NiK-21273 is a NOP receptor antagonist <Reference id=38326/>. It has demonstrated antiparkinsonian effects in in vivo models.
iupac name: 2-[3-[[4-(2-chloro-6-fluorophenyl)piperidin-1-yl]methyl]-2-(morpholine-4-carbonyl)indol-1-yl]acetamide
synonym: NiK21273
approved: f
ligand name: NiK-21273
type: SyntheticOrganicLigand

TRAP-101
in ch i key: DCRGHMJXEBSRQG-UHFFFAOYSA-N
in ch i: InChI=1S/C24H35N3O2/c1-2-26-22-12-8-9-13-23(22)27(24(26)29)21-14-15-25(17-20(21)18-28)16-19-10-6-4-3-5-7-11-19/h8-9,12-13,19,28H,2-7,10-11,14-18H2,1H3
comment: TRAP-101 is an achiral analogue of the NOP receptor antagonist <Ligand id=1691/> <Reference id=38325/>. Despite its lack of chirality TRAP-101's pharmacological profile is similar to that of J-113397, but it is more easily synthesised.
iupac name: 1-[1-(cyclooctylmethyl)-5-(hydroxymethyl)-3,6-dihydro-2H-pyridin-4-yl]-3-ethylbenzimidazol-2-one
xref: CHEMBL3182208
synonym: Trap101
approved: f
ligand name: TRAP-101
type: SyntheticOrganicLigand

compound 8 [PMID: 25898023]
in ch i key: MXWDBTLNBKIMEX-UHFFFAOYSA-N
in ch i: InChI=1S/C28H23FN4O4/c1-37-28(36)17-7-9-22(10-8-17)32-26(34)19-4-2-3-18(13-19)23-14-20(5-6-21(23)15-30)27(35)33-25-11-12-31-16-24(25)29/h2-14,16H,15,30H2,1H3,(H,32,34)(H,31,33,35)
comment: Compound 8 [PMID: 25898023] is a selective inhibitor of Rho kinase (ROCK) activity that was developed for the treatment of ocular inflammation <Reference id=38299/>. In an effort to reduce unintended systemic ROCK-associated side effects and maximise local effects, it was designed to be rapidly converted to an inactive metabolite in the systemic circulation. Compounds of this type are known as 'soft' drugs. Specifically, compound 8 contains an ester group that is hydrolysed by blood esterases to an inactive carboxylic acid metabolite (8M). Amakem Ophthalmics have a 'soft' ROCK inhibitor AMA0076 that has been shown to reduce intraocular pressure in a rabbit model of glaucoma <Reference id=38300/>, and which has completed Phase 2 clinical evaluation in glaucoma/ocular hypertension (NCT01693315). The structure of AMA0076 has not been formally disclosed, but it appears to be derived from the same chemical scaffold as compound 8.
iupac name: methyl 4-[[3-[2-(aminomethyl)-5-[(3-fluoropyridin-4-yl)carbamoyl]phenyl]benzoyl]amino]benzoate
xref: CHEMBL3426624
approved: f
ligand name: compound 8 [PMID: 25898023]
type: SyntheticOrganicLigand

NSC80734
in ch i key: NKTXGJQCHFJKQJ-UHFFFAOYSA-N
in ch i: InChI=1S/C28H20N6O3/c29-17-19-1-5-21(6-2-19)31-27(35)33-23-9-13-25(14-10-23)37-26-15-11-24(12-16-26)34-28(36)32-22-7-3-20(18-30)4-8-22/h1-16H,(H2,31,33,35)(H2,32,34,36)
comment: NSC80734 is a small molecule protein-protein interaction inhibitor that disrupts human IL-18 binding to the ectromelia virus IL-18 binding protein (IL-18BP) <Reference id=38291/>. IL-18BP acts as endogenous antagonist of IL-18 activity. By sequestering circulating IL-18 it modulates the amount of free IL-18 able to activate its receptor and downstream signalling cascade. NSC80734 binds in to the interaction site on IL-18 that engages IL-18BP, and thus it acts as an IL-18BP mimetic.
xref: CHEMBL1304177
approved: f
ligand name: NSC80734
type: SyntheticOrganicLigand

GSK2603566A
in ch i key: APVMUACUMAKXLA-UHFFFAOYSA-N
in ch i: InChI=1S/C27H30N4O3/c32-26(33)16-24(21-4-1-3-20(15-21)18-6-7-18)31-25-11-10-23(17-29-25)34-14-12-22-9-8-19-5-2-13-28-27(19)30-22/h1,3-4,8-11,15,17-18,24H,2,5-7,12-14,16H2,(H,28,30)(H,29,31)(H,32,33)
comment: GSK2603566A is a pan αv integrin antagonist <Reference id=38289/>. It is orally bioavailable and exhibits anti-fibrotic activity. GSK2603566A was tested as the racemic mixture of enantiomers.
iupac name: 3-(3-Cyclopropylphenyl)-3-((5-(2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy)pyridin-2-yl)amino)propanoic acid
synonym: compound 39 [PMID: 31497959]
approved: f
ligand name: GSK2603566A
type: SyntheticOrganicLigand

fadraciclib
in ch i key: DLPIYBKBHMZCJI-WBVHZDCISA-N
in ch i: InChI=1S/C21H31N7O/c1-7-17(15(6)29)25-21-26-19(18-20(27-21)28(11-24-18)12(2)3)23-10-16-9-22-14(5)8-13(16)4/h8-9,11-12,15,17,29H,7,10H2,1-6H3,(H2,23,25,26,27)/t15-,17+/m1/s1
comment: Fadraciclib (CYC065) is a cyclin-dependent kinase 2 and 9 inhibitor that is claimed as compound [1] in patent WO2008122767A2 <Reference id=38197/>. Structurally CYC065 is a derivative of <Ligand id=6035/> (CYC202). It was developed by Cyclacel for potential to treat proliferative disorders including cancer, leukemia and psoriasis.
iupac name: (2R,3S)-3-[[6-[(4,6-dimethylpyridin-3-yl)methylamino]-9-propan-2-ylpurin-2-yl]amino]pentan-2-ol
xref: CHEMBL3655762
synonym: CYC065
synonym: CYC-065
approved: f
ligand name: fadraciclib
type: SyntheticOrganicLigand

CWHM12
in ch i key: YDHAGPCZRFQPOI-NRFANRHFSA-N
in ch i: InChI=1S/C26H32BrN5O6/c1-26(2,3)16-4-14(5-17(27)8-16)21(10-23(36)37)32-22(35)13-28-24(38)15-6-18(9-19(33)7-15)31-25-29-11-20(34)12-30-25/h4-9,20-21,33-34H,10-13H2,1-3H3,(H,28,38)(H,32,35)(H,36,37)(H2,29,30,31)/t21-/m0/s1
comment: CWHM12 is a pan αv integrin antagonist <Reference id=38288/>. It was used to determine that αv integrin activation regulates fibrosis in models of organ fibrosis. These findings suggest that targeting all αv integrins may have clinical utility in the treatment of a broad range of fibrotic diseases. The S enantiomer of CWHM12 is the bioactive form; the R enantiomer does not inhibit any of the five αv-containing integrins in vitro. Structurally, CWHM12 is a small-molecule RGD peptidomimetic antagonist in which the arginine (R) mimetic is a cyclic guanidino-substituted phenyl group and the aspartic acid (D) mimetic is a phenyl-substituted β amino acid. These two residues are linked by a glycine (G).
iupac name: (3S)-3-(3-bromo-5-tert-butylphenyl)-3-[[2-[[3-hydroxy-5-[(5-hydroxy-1,4,5,6-tetrahydropyrimidin-2-yl)amino]benzoyl]amino]acetyl]amino]propanoic acid
xref: CHEMBL3319237
synonym: CWHM-12
synonym: CWHM 12
approved: f
ligand name: CWHM12
type: SyntheticOrganicLigand

SWE101
in ch i key: UIADWSXPNFQQCZ-UHFFFAOYSA-N
in ch i: InChI=1S/C19H15Cl2NO3/c20-14-10-9-13(11-15(14)21)18-19(12-5-2-1-3-6-12)25-16(22-18)7-4-8-17(23)24/h1-3,5-6,9-11H,4,7-8H2,(H,23,24)
comment: SWE101 is a soluble epoxide hydrolase (sEH; EPHX2) inhibitor that selectively, and competitively targets the enzyme's phosphatase activity <Reference id=38286/>. Its structure was developed from the scaffold of the NSAID <Ligand id=7252/> which exhibits weak sEH-phosphatase inhibitory activity <Reference id=38287/>. SWE101 is a tool compound that was designed to aid investigations of the physiological and pathophysiological role of sEH phosphatase activity in vivo.
iupac name: 4-[4-(3,4-dichlorophenyl)-5-phenyl-1,3-oxazol-2-yl]butanoic acid
synonym: compound 22b [PMID: 31436984]
approved: f
ligand name: SWE101
type: SyntheticOrganicLigand

MK-4815
canonical SMILES: NCc1c(O)cc(cc1C(C)(C)C)C(C)(C)C
isomeric SMILES: NCc1c(O)cc(cc1C(C)(C)C)C(C)(C)C
in ch i key: ZUSLEOOZAITYGH-UHFFFAOYSA-N
in ch i: InChI=1S/C15H25NO/c1-14(2,3)10-7-12(15(4,5)6)11(9-16)13(17)8-10/h7-8,17H,9,16H2,1-6H3
comment: MK-4815 is a small molecule with promising antimalarial activity <Reference id=37889/>. The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
iupac name: 2-(aminomethyl)-3,5-ditert-butylphenol
xref: CHEMBL1191888
synonym: MK4815
approved: f
ligand name: MK-4815
type: SyntheticOrganicLigand

compound 1 [PMID: 31465224]
in ch i key: UOGAVVINOTWELT-UHFFFAOYSA-N
in ch i: InChI=1S/C29H23F3N4O2/c1-3-27(37)34-23-12-15-25(16-13-23)36-26(18-24(35-36)14-17-28(38)33-2)21-6-4-19(5-7-21)20-8-10-22(11-9-20)29(30,31)32/h1,4-13,15-16,18H,14,17H2,2H3,(H,33,38)(H,34,37)
comment: Compound 1 is reported as an irreversible inhibitor of the M2 splice form of pyruvate kinase (PKM2) <Reference id=38285/>. It targets both the metabolic and oncogenic functions of PKM2 and mediates antitumour effects in vitro and in vivo. The covalent PKM2 binding residues have been identified as Cys317 and Cys326 which are close to the enzyme's substrate-binding site.
iupac name: N-(4-{3-[2-(methylcarbamoyl)ethyl]-5-[4'-(trifluoromethyl)-[1,1'-biphenyl]-4-yl]-1H-pyrazol-1-yl}phenyl)prop-2-ynamide
approved: f
ligand name: compound 1 [PMID: 31465224]
type: SyntheticOrganicLigand

SS-208
in ch i key: JFGOILLZIAIYGA-UHFFFAOYSA-N
comment: SS-208 is reported as an isotype selective inhibitor of histone deacetylase 6 (HDAC6) <Reference id=38267/>. It has been developed for potential to treat advanced melanoma. SS-208 has been designed to provide improved HDAC6 selectivity compared to <Ligand id=7010/> and <Ligand id=9426/> which both exhibit unfavourable levels of HDAC1 inhibition. Selective pharmacological inhibition or genetic abrogation of HDAC6 modulates immune checkpoint activity by downregulating the expression of PD-L1 via the recruitment and activation of STAT3 <Reference id=38268/>. The antitumour activity of SS-208 in vivo is primarily mediated by activation of immune cells and an anti-tumour immune response in the tumour microenvironment.
synonym: compound 7b [PMID: 31414801]
synonym: SS208
approved: f
ligand name: SS-208
type: SyntheticOrganicLigand

casein kinase II inhibitor III
canonical SMILES: OC(=O)C=Cc1cc(Br)c(c(c1Br)Br)Br
isomeric SMILES: OC(=O)/C=C/c1cc(Br)c(c(c1Br)Br)Br
in ch i key: SVJQCVOKYJWUBC-OWOJBTEDSA-N
in ch i: InChI=1S/C9H4Br4O2/c10-5-3-4(1-2-6(14)15)7(11)9(13)8(5)12/h1-3H,(H,14,15)/b2-1+
comment: TBCA is a selective, cell-permeable inhibitor of casein kinase 2 (CK2) and has minimal effect on a panel of 28 other kinases <Reference id=25981/>.
iupac name: (2E)-3-(2,3,4,5-tetrabromophenyl)prop-2-enoic acid
xref: CHEMBL270724
synonym: tetrabromocinnamic acid
synonym: TBCA
approved: f
ligand name: casein kinase II inhibitor III
type: SyntheticOrganicLigand

compound 12b [PMID: 31465220]
in ch i key: KUZSBKJSGSKPJH-VXGBXAGGSA-N
in ch i: InChI=1S/C18H23N7O2/c1-11-9-26-4-2-24(11)17-13-6-12-10-27-5-3-25(12)18(13)23-16(22-17)14-7-21-15(19)8-20-14/h7-8,11-12H,2-6,9-10H2,1H3,(H2,19,21)/t11-,12-/m1/s1
comment: Compound 12b is a novel conformationally restricted, potent mTOR inhibitor <Reference id=38266/>. Although it is an ATP-competitive inhibitor, its novel chemical scaffold dictates it selectivity.
iupac name: 5-((R)-4-((R)-3-Methylmorpholino)-5a,6,8,9-tetrahydro-5H-pyrimido[5',4':4,5]pyrrolo[2,1-c][1,4]oxazin-2-yl)pyrazin-2-amine
approved: f
ligand name: compound 12b [PMID: 31465220]
type: SyntheticOrganicLigand

compound 10 [PMID: 31411465]
in ch i key: UHBPMQISVQNVGD-PDOMDSBESA-N
in ch i: InChI=1S/C28H37N3O3/c1-2-3-10-23-12-6-15-30(23)27(32)22-9-4-7-20(16-22)21-8-5-11-24(17-21)31-26(19-13-14-19)25(18-29-31)28(33)34/h5,8,11,17-20,22-23H,2-4,6-7,9-10,12-16H2,1H3,(H,33,34)/t20-,22+,23?/m0/s1
comment: Compound 10 is small molecule that binds to KEAP1 and prevents its interaction with the Nrf2 transcription factor <Reference id=38262/>. It acts as a functional activator of Nrf2-mediated gene transcription. The chemical structure was originally claimed in a Glaxosmithkline/Astex Therapeutics patent <Reference id=38261/>.
iupac name: 1-(3-((cis)-3-(2-Butylpyrrolidine-1-carbonyl)cyclohexyl)phenyl)-5-cyclopropyl-1H-pyrazole-4-carboxylic acid
synonym: example 8 (cis racemate) [WO2017060855A1]
approved: f
ligand name: compound 10 [PMID: 31411465]
type: SyntheticOrganicLigand

RA839
in ch i key: BVYWIQHJXAEJOD-IBGZPJMESA-N
in ch i: InChI=1S/C25H28N2O4S/c1-15-13-16(2)18(4)24(17(15)3)32(30,31)26-22-9-10-23(21-8-6-5-7-20(21)22)27-12-11-19(14-27)25(28)29/h5-10,13,19,26H,11-12,14H2,1-4H3,(H,28,29)/t19-/m0/s1
comment: RA839 is a small molecule that noncovalently interacts with KEAP1 and acts as a selective activator of Nrf2-mediated gene transcription <Reference id=38260/>. RA839-induced activation of the Nrf2/ARE pathway is reported to produce an anti-rotaviral effect, via inhibition of rotavirus propagation, in vitro <Reference id=38263/>.
iupac name: (3S)-1-[4-[(2,3,5,6-tetramethylphenyl)sulfonylamino]naphthalen-1-yl]pyrrolidine-3-carboxylic acid
xref: CHEMBL3899754
synonym: RA-839
synonym: compound 7 [PMID: 31411465]
approved: f
ligand name: RA839
type: SyntheticOrganicLigand

compound 21b [PMID: 31430136]
in ch i key: VIYHDQCOPYIJMF-UHFFFAOYSA-N
in ch i: InChI=1S/C16H18N4O2S2/c1-3-11-4-12(13-8-19-20(2)10-13)6-14(5-11)24(21,22)16-9-18-15(7-17)23-16/h4-6,8-10H,3,7,17H2,1-2H3
comment: Compound 21b is an experimental, selective and irreversible inhibitor of LOXL2 that has an aminomethylenethiazole (AMTz) scaffold <Reference id=38256/>.
iupac name: [5-[3-ethyl-5-(1-methylpyrazol-4-yl)phenyl]sulfonyl-1,3-thiazol-2-yl]methanamine
approved: f
ligand name: compound 21b [PMID: 31430136]
type: SyntheticOrganicLigand

CCT365623
in ch i key: ADIBEGOVRYXDOX-UHFFFAOYSA-N
in ch i: InChI=1S/C18H17NO4S3/c1-25(20,21)16-9-14(13-5-3-2-4-6-13)10-17(11-16)26(22,23)18-8-7-15(12-19)24-18/h2-11H,12,19H2,1H3
comment: CCT365623 is an experimental aminomethylenethiophene type dual LOX/LOXL2 inhibitor. Orally administered CCT365623 mediates anti-tumour and anti-metastatic effects in vivo <Reference id=38259/>.
iupac name: [5-(3-methylsulfonyl-5-phenylphenyl)sulfonylthiophen-2-yl]methanamine
synonym: compound 9f [PMID: 31070916]
approved: f
ligand name: CCT365623
type: SyntheticOrganicLigand

RJW100
in ch i key: ZFXMYHPLTQTTFW-XZSHQJGLSA-N
in ch i: InChI=1S/C28H34O/c1-3-4-5-8-17-24-20-25-26(29)18-19-28(25,21(2)22-13-9-6-10-14-22)27(24)23-15-11-7-12-16-23/h6-7,9-16,25-26,29H,2-5,8,17-20H2,1H3/t25?,26-,28+/m1/s1
comment: RJW100 is a small-molecule synthetic agonist of the orphan nuclear receptors, liver receptor homolog 1 (hLRH-1; NR5A2) and steroidogenic factor-1 (SF-1; NR5A1) <Reference id=38250/>. It has good solubility and stability and is suitable as an experimental tool compound.
iupac name: rac-(1R,5R,6R)-3-Hexyl-6-hydroxy-2-phenyl-1-(phenylvinyl)-bicyclo[3.3.0]oct-2-ene
synonym: 24-exo
approved: f
ligand name: RJW100
type: SyntheticOrganicLigand

compound 6N [PMID: 31419141]
in ch i key: COQCBADNBTZWQG-KKGVWULHSA-N
in ch i: InChI=1S/C28H36N2O2S/c1-3-4-5-8-17-24-20-25-26(30-33(29,31)32)18-19-28(25,21(2)22-13-9-6-10-14-22)27(24)23-15-11-7-12-16-23/h6-7,9-16,25-26,30H,2-5,8,17-20H2,1H3,(H2,29,31,32)/t25?,26-,28-/m0/s1
comment: Compound 6N is reported as a low nanomolar potency agonist of the nuclear hormone receptor, liver receptor homolog-1 (LRH-1; NR5A2) <Reference id=38249/>. It does not exhibit agonist activity at the related receptor, steroidogenic factor 1 (SF-1; NR5A1). LRH-1 has no known endogenous ligand.
iupac name: Endo 5-Hexyl-4-phenyl-3a-(1-phenylvinyl)-1,2,3,3a,6,6a-hexahydropentalen-1-yl sulfamide
approved: f
ligand name: compound 6N [PMID: 31419141]
type: SyntheticOrganicLigand

compound 16 [PMID: 31498617]
in ch i key: BWEJNHRMGZUMNU-UHFFFAOYSA-N
in ch i: InChI=1S/C23H21N3O4S/c1-15-7-10-19(26-31(27,28)22-6-4-3-5-20(22)29-2)21(13-15)30-17-8-9-18-16(14-17)11-12-25-23(18)24/h3-14,26H,1-2H3,(H2,24,25)
comment: Compound 16 is reported as a novel, selective agonist of the class A orphan GPCR, MRGPRX1 <Reference id=38247/>. Compound 16 is extensively metabolised in mouse liver microsomes and this probably accounts for the short in vivo half-life (~20 m in) that was observed following intravenous administration in mice.
iupac name: N-(2-(1-Aminoisoquinolin-6-yloxy)-4-methylphenyl)-2-methoxybenzenesulfonamide
approved: f
ligand name: compound 16 [PMID: 31498617]
type: SyntheticOrganicLigand

compound 1 [PMID: 31477924]
in ch i key: GDBAAUWGHRTFSE-UHFFFAOYSA-N
in ch i: InChI=1S/C23H14F3N5O/c1-14-7-9-19-21(18(14)10-8-17-13-27-20-6-3-11-28-31(17)20)32-30-22(19)29-16-5-2-4-15(12-16)23(24,25)26/h2-7,9,11-13H,1H3,(H,29,30)
comment: Compound 1 is a discoidin domain receptor tyrosine kinase 1 (DDR1) inhibitor <Reference id=38243/>. Its discovery/design was advanced using a deep learning model named generative tensorial reinforcement learning (GENTRL). Using GENTRL compound 1 was identified in only 21 days.
approved: f
ligand name: compound 1 [PMID: 31477924]
type: SyntheticOrganicLigand

BAY-293
in ch i key: WEGLOYDTDILXDA-OAHLLOKOSA-N
in ch i: InChI=1S/C25H28N4O2S/c1-15(24-10-18(14-32-24)19-9-7-6-8-17(19)13-26-3)27-25-20-11-22(30-4)23(31-5)12-21(20)28-16(2)29-25/h6-12,14-15,26H,13H2,1-5H3,(H,27,28,29)/t15-/m1/s1
comment: BAY-293 (compound 23) inhibits RAS pathway signalling by disrupting the protein-protein interaction between the RAS GTPase and its nucleotide exchange factor SOS1 <Reference id=38242/>. This mechanism mediates an antiproliferative effect. It is suitable as a pharmacological tool to investigate the potential of KRAS/SOS1 modulation in treating proliferative diseases, and it is functional for all KRAS variants.
iupac name: 6,7-dimethoxy-2-methyl-N-[(1R)-1-[4-[2-(methylaminomethyl)phenyl]thiophen-2-yl]ethyl]quinazolin-4-amine
synonym: BAY293
synonym: compound 23 [PMID: 30683722]
approved: f
ligand name: BAY-293
type: SyntheticOrganicLigand

AZD9898
in ch i key: RVMWIVNHZMXEHS-UWVGGRQHSA-N
comment: AZD9898 is an orally active inhibitor of leukotriene C4 synthase (LTC4S) that was developed for the treatment of asthma <Reference id=38238/>.
iupac name: (1S,2S)-2-[5-(5-chloro-2,4-difluoro-N-(2-fluoro-2-methylpropyl)anilino)-3-methoxypyrazine-2-carbonyl]cyclopropane-1-carboxylic acid
xref: CHEMBL3961833
synonym: example 62 [WO2016177845A1]
synonym: AZD-9898
approved: f
ligand name: AZD9898
type: SyntheticOrganicLigand

bemcentinib
in ch i key: KXMZDGSRSGHMMK-VWLOTQADSA-N
in ch i: InChI=1S/C30H34N8/c31-29-33-30(32-24-13-10-20-11-14-25(15-12-22(20)18-24)37-16-3-4-17-37)36-38(29)27-19-23-8-5-7-21-6-1-2-9-26(21)28(23)35-34-27/h1-2,6,9-10,13,18-19,25H,3-5,7-8,11-12,14-17H2,(H3,31,32,33,36)/t25-/m0/s1
comment: Bemcentinib (BGB324, R428) is a potent, selective and orally active AXL receptor tyrosine kinase inhibitor that was discovered by Rigel as R428 <Reference id=38235/> and which is being developed by BergenBio for anti-cancer potential <Reference id=38236/>.
xref: CHEMBL3809489
synonym: BGB-324
synonym: BGB 324
synonym: R-428
synonym: R428
synonym: BGB324
approved: f
ligand name: bemcentinib
type: SyntheticOrganicLigand

naringenin
canonical SMILES: Oc1ccc(cc1)C1CC(=O)c2c(O1)cc(cc2O)O
isomeric SMILES: Oc1ccc(cc1)C1CC(=O)c2c(O1)cc(cc2O)O
in ch i key: FTVWIRXFELQLPI-UHFFFAOYSA-N
in ch i: InChI=1S/C15H12O5/c16-9-3-1-8(2-4-9)13-7-12(19)15-11(18)5-10(17)6-14(15)20-13/h1-6,13,16-18H,7H2
comment: Naringenin is a citrus fruit flavanone. It acts as an inhibitor of TRPM3 ion channel activity <Reference id=37313/><Reference id=37314/>.
iupac name: 5,7-dihydroxy-2-(4-hydroxyphenyl)-2,3-dihydrochromen-4-one
xref: CHEMBL32571
synonym: naringetol
synonym: BE-14348A
approved: f
ligand name: naringenin
type: NaturalProductLigand

furmonertinib
in ch i key: GHKOONMJXNWOIW-UHFFFAOYSA-N
in ch i: InChI=1S/C28H31F3N8O2/c1-6-24(40)33-21-15-22(26(41-17-28(29,30)31)36-25(21)38(4)14-13-37(2)3)35-27-32-12-11-20(34-27)19-16-39(5)23-10-8-7-9-18(19)23/h6-12,15-16H,1,13-14,17H2,2-5H3,(H,33,40)(H,32,34,35)
comment: Furmonertinib (AST2818; alflutinib) is a receptor tyrosine kinase inhibitor that targets mutant forms of the EGFR more effectively than the wild type receptor kinase, with notable potency vs. the T790M resistance mutation. It has an irreversible binding mode. AST2818's chemical structure is claimed as example 3 in Shanghai Allist Pharmaceuticals' patent US10072002B2 <Reference id=38234/>. Note that AST2818 is administered clinically as the mesylate.
iupac name: N-[2-[2-(dimethylamino)ethyl-methylamino]-5-[[4-(1-methylindol-3-yl)pyrimidin-2-yl]amino]-6-(2,2,2-trifluoroethoxy)pyridin-3-yl]prop-2-enamide
synonym: alflutinib (pseudo INN)
synonym: AST 2818
synonym: AST-2818
synonym: example 3 [US10072002B2]
synonym: ASK120067
synonym: AST2818
synonym: Ivesa®
approved: t
ligand name: furmonertinib
type: SyntheticOrganicLigand

telatinib
in ch i key: QFCXANHHBCGMAS-UHFFFAOYSA-N
in ch i: InChI=1S/C20H16ClN5O3/c1-22-19(27)16-10-12(6-8-23-16)11-29-20-17-15(7-9-28-17)18(25-26-20)24-14-4-2-13(21)3-5-14/h2-10H,11H2,1H3,(H,22,27)(H,24,25)
comment: Telatinib (BAY-579352) is an orally available VEGFR2/3 and PDGFRβ receptor tyrosine kinase inhibitor that exhibits potent anti-angiogenic activity which translates to anti-tumour efficacy in vitro and in vivo. The chemical structure of telatinib is claimed in Bayer's patent WO2001023375A2 (as example 14) <Reference id=38233/>.
iupac name: 4-[[4-(4-chloroanilino)furo[2,3-d]pyridazin-7-yl]oxymethyl]-N-methylpyridine-2-carboxamide
xref: CHEMBL2079588
synonym: BAY-579352
synonym: BAY579352
synonym: BAY 57-9352
synonym: Bay-57-9352
synonym: example 14 [WO2001023375A2]
approved: f
ligand name: telatinib
type: SyntheticOrganicLigand

ibcasertib
in ch i key: BRKWREZNORONDU-UHFFFAOYSA-N
in ch i: InChI=1S/C27H21N3O3/c1-32-18-9-12-22-25(16-18)29-14-13-26(22)33-19-10-11-20-17(15-19)5-4-6-21(20)27(31)30-24-8-3-2-7-23(24)28/h2-16H,28H2,1H3,(H,30,31)
comment: CS2164 is a multi-target kinase inhibitor that exerts anti-angiogenic, anti-mitotic and anti-inflammatory effects that mediate anti-tumour activity <Reference id=38228/>. Via inhibition of Aurora B CS2164 mediates inhibition of histone 3 (H3) phosphorylation which is associated with cell cycle arrest. CS2164 was developed by Chipscreen Biosciences and is claimed in their patent US20100298358A1 <Reference id=38229/>. CS2164's chemical structure is an axact match for the INN 'ibcasertib' which was released in the WHO's proposed INN list 127 on 21 July 2022.
iupac name: N-(2-aminophenyl)-6-(7-methoxyquinolin-4-yl)oxynaphthalene-1-carboxamide
synonym: chiauranib (pseudo INN)
synonym: CS-2164
synonym: example 32 [US20100298358A1]
synonym: CS2164
approved: f
ligand name: ibcasertib
type: SyntheticOrganicLigand

belizatinib
in ch i key: WSTUJEXAPHIEIM-UHFFFAOYSA-N
in ch i: InChI=1S/C33H44FN5O3/c1-21(2)35-30(40)24-8-12-27(13-9-24)39-29-19-22(20-38-17-15-25(16-18-38)33(3,4)42)5-14-28(29)36-32(39)37-31(41)23-6-10-26(34)11-7-23/h5-7,10-11,14,19,21,24-25,27,42H,8-9,12-13,15-18,20H2,1-4H3,(H,35,40)(H,36,37,41)
comment: Belizatinib (TSR-011) is an inhibitor of anaplastic lymphoma kinase (ALK) <Reference id=19607/>. It is reported as being potent, selective, and orally bioavailable, and was designed by Tesaro for potential anti-tumour activity.
iupac name: 4-fluoro-N-[6-[[4-(2-hydroxypropan-2-yl)piperidin-1-yl]methyl]-1-[4-(propan-2-ylcarbamoyl)cyclohexyl]benzimidazol-2-yl]benzamide
xref: CHEMBL2172308
synonym: TSR-011
synonym: TSR011
synonym: compound 36 [PMID: 22734674]
approved: f
ligand name: belizatinib
type: SyntheticOrganicLigand

mitapivat
in ch i key: XAYGBKHKBBXDAK-UHFFFAOYSA-N
in ch i: InChI=1S/C24H26N4O3S/c29-24(28-15-13-27(14-16-28)17-18-6-7-18)20-8-10-21(11-9-20)26-32(30,31)22-5-1-3-19-4-2-12-25-23(19)22/h1-5,8-12,18,26H,6-7,13-17H2
comment: Mitapivat (AG-348) is a first-in-class, small molecule allosteric activator of the pyruvate kinases. It activates the PK isoform that is found in erythrocytes (PKR protein that is expressed from the PKLR gene) and the embryonic PKM2 isoform (expressed from the PKM gene) that is only expressed by cancer cells in adult tissues. Mitapivat was developed by Agios Pharmaceuticals as a novel therapy for diseases of red blood cells that are associated with inherited PKR deficiency <Reference id=38226/>, and for potential in cancer therapy via activation of PKM2. Activation of PK in red cells increases hemoglobin levels <Reference id=41078/><Reference id=41351/>. The active drug is the sulfate hydrate (PubChem CID 134693700). We show the structure for the parent molecule as described by its INN.
synonym: AG-348
synonym: AG348
synonym: PKM2 activator 1020
synonym: PKR-IN-1
synonym: compound 80a [WO2011002817A1]
synonym: Pyrukynd®
approved: t
ligand name: mitapivat
type: SyntheticOrganicLigand

mepenzolic acid
canonical SMILES: O=C(C(c1ccccc1)(c1ccccc1)O)OC1CCC[N+](C1)(C)C
isomeric SMILES: O=C(C(c1ccccc1)(c1ccccc1)O)OC1CCC[N+](C1)(C)C
in ch i key: GKNPSSNBBWDAGH-UHFFFAOYSA-N
in ch i: InChI=1S/C21H26NO3/c1-22(2)15-9-14-19(16-22)25-20(23)21(24,17-10-5-3-6-11-17)18-12-7-4-8-13-18/h3-8,10-13,19,24H,9,14-16H2,1-2H3/q+1
comment: In in vitro binding assays, (R)-mepenzolate has a higher affinity for the human M2 and M3 muscarinic acetylcholine receptors than (S)-mepenzolate <Reference id=38216/>.
iupac name: (1,1-dimethylpiperidin-1-ium-3-yl) 2-hydroxy-2,2-diphenylacetate
xref: CHEMBL524004
synonym: mepenzolate
synonym: Cantril®
synonym: glycophenylate
synonym: (±)-mepenzolate
synonym: racemic mepenzolate
approved: t
ligand name: mepenzolic acid
type: SyntheticOrganicLigand

mobocertinib
in ch i key: AZSRSNUQCUDCGG-UHFFFAOYSA-N
in ch i: InChI=1S/C32H39N7O4/c1-9-29(40)34-24-16-25(28(42-8)17-27(24)38(6)15-14-37(4)5)35-32-33-18-22(31(41)43-20(2)3)30(36-32)23-19-39(7)26-13-11-10-12-21(23)26/h9-13,16-20H,1,14-15H2,2-8H3,(H,34,40)(H,33,35,36)
comment: Mobocertinib (TAK-788) is an oral EGFR/HER2 tyrosine kinase inhibitor that is claimed in Ariad Pharmaceuticals' patent WO2015195228A1 <Reference id=38207/>. It inhibits EGFR and HER2 with activating/resistance mutations, including rare EGFR Ins20 (exon 20 insertion) resistance mutations <Reference id=42944/><Reference id=42946/> and was progressed by Takeda Pharmaceuticals as an advanced therapy for metastatic NSCLC with this exon 20 insertion <Reference id=41390/><Reference id=42945/>.
iupac name: propan-2-yl 2-[4-[2-(dimethylamino)ethyl-methylamino]-2-methoxy-5-(prop-2-enoylamino)anilino]-4-(1-methylindol-3-yl)pyrimidine-5-carboxylate
synonym: example 94 [WO2015195228A1]
synonym: AP32788
synonym: TAK-788
synonym: TAK788
synonym: Exkivity®
approved: t
ligand name: mobocertinib
type: SyntheticOrganicLigand

mevociclib
in ch i key: SCJNYBYSTCRPAO-LXBQGUBHSA-N
in ch i: InChI=1S/C31H35ClN8O2/c1-31(39-29(42)26-13-12-21(17-33-26)36-27(41)11-7-15-40(2)3)14-6-8-20(16-31)37-30-35-19-24(32)28(38-30)23-18-34-25-10-5-4-9-22(23)25/h4-5,7,9-13,17-20,34H,6,8,14-16H2,1-3H3,(H,36,41)(H,39,42)(H,35,37,38)/b11-7+/t20-,31+/m1/s1
comment: Mevociclib (SY-1365) is a cyclin-dependent kinase 7 (CDK7) inhibtor <Reference id=38211/> that is claimed in Syros Pharmaceuticals' patent WO2015154039A2 <Reference id=38206/>. It is being developed for potential to treat proliferative diseases. SY-1365 is a structural analogue of <Ligand id=8052/>, and it covalently binds to the same cysteine residue located outside of the canonical kinase domain at which THZ1 binds.
iupac name: N-[(1S,3R)-3-[[5-chloro-4-(1H-indol-3-yl)pyrimidin-2-yl]amino]-1-methylcyclohexyl]-5-[[(E)-4-(dimethylamino)but-2-enoyl]amino]pyridine-2-carboxamide
synonym: SY-1365
synonym: compound 264 [WO2015154039A2]
synonym: SY1365
approved: f
ligand name: mevociclib
type: SyntheticOrganicLigand

linperlisib
in ch i key: NVWKNQGHVMMAJW-UHFFFAOYSA-N
in ch i: InChI=1S/C28H37FN6O5S/c1-28(2,36)20-5-7-34(8-6-20)17-19-13-21(29)15-22-24(31-27(32-25(19)22)35-9-11-40-12-10-35)18-14-23(33-41(4,37)38)26(39-3)30-16-18/h13-16,20,33,36H,5-12,17H2,1-4H3
comment: Linperlisib (YY-20394) is a PI3Kδ inhibitor claimed by Shanghai Yingli Pharmaceutical Company in their patent US20160244432A1 (as compound 10) <Reference id=38205/>.
iupac name: N-[5-[6-fluoro-8-[[4-(2-hydroxypropan-2-yl)piperidin-1-yl]methyl]-2-morpholin-4-ylquinazolin-4-yl]-2-methoxypyridin-3-yl]methanesulfonamide
synonym: YY-20394
synonym: PI3Kdelta-IN-2
synonym: compound 10 [US20160244432]
synonym: YY20394
approved: f
ligand name: linperlisib
type: SyntheticOrganicLigand

E209
in ch i key: RDWGXWFRQYUDIZ-UHFFFAOYSA-N
in ch i: InChI=1S/C29H40FNO5/c30-26-7-11-31(12-8-26)13-14-32-27-3-1-22(2-4-27)23-5-9-28(10-6-23)33-35-29(36-34-28)24-16-20-15-21(18-24)19-25(29)17-20/h1-4,20-21,23-26H,5-19H2
comment: E209 is a fully synthetic tetraoxane analogue with potent antimalarial activity <Reference id=38217/>. The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
iupac name: 1-[2-(4-{dispiro[adamantane-2,2'-[1,3,4,6]tetraoxane-5',1''-cyclohexan]-4''-yl}phenoxy)ethyl]-4-fluoropiperidine
xref: CHEMBL4288940
approved: f
ligand name: E209
type: SyntheticOrganicLigand

elsubrutinib
in ch i key: UNHZLHSLZZWMNP-LLVKDONJSA-N
in ch i: InChI=1S/C17H19N3O2/c1-2-15(21)20-9-3-4-11(10-20)12-5-6-14(17(18)22)16-13(12)7-8-19-16/h2,5-8,11,19H,1,3-4,9-10H2,(H2,18,22)/t11-/m1/s1
comment: Elsubrutinib (example #30 (S) [WO2014210255A1]) is the (S) stereoenantiomer of example #30 from Abbvie's patent WO2014210255A1 which claims BTK inhibitors for their potential to treat immunological and oncological conditions <Reference id=38203/>. Example #30 (S) could be ABBV-105, an Abbvie BTK inhibitor that is being evaluated in combination with <Ligand id=9246/> (ABT-494, a JAK1 inhibitor) in patients with rheumatoid arthritis or systemic lupus erythematosus (the combination is coded ABBV-599). Although preclinical efficacy has been reported <Reference id=38204/>, the structure of ABBV-105 has not been formally disclosed, so the name-to-structure alluded to here is speculative and provided in good faith.
iupac name: 4-[(3S)-1-prop-2-enoylpiperidin-3-yl]-1H-indole-7-carboxamide
synonym: example #30 (S) [WO2014210255A1]
approved: f
ligand name: elsubrutinib
type: SyntheticOrganicLigand

milategrast
in ch i key: PGWIKFFLIJECAM-UHFFFAOYSA-N
in ch i: InChI=1S/C24H38N2/c1-23(2)15-20(16-24(3,4)18-23)21-7-5-6-8-22(21)26-13-11-25(12-14-26)17-19-9-10-19/h5-8,19-20H,9-18H2,1-4H3
comment: Milategrast (example 9) is claimed in Esai Co.'s patent US20050261291A1 as the hydrochloride salt <Reference id=38202/>. The chemical structures in this patent are claimed for their potential to treat inflammatory and autoimmune diseases that are associated with adhesion and infiltration of leukocytes (e.g. inflammatory bowel disease, rheumatoid arthritis, psoriasis, multiple sclerosis, asthma and atopic dermatitis). We show just the parent molecule. In INN proposed list 121 (August 2019) milategrast is described as a non-steroidal anti-inflammatory agent. Review of Esai's epipeline document and other online reports suggests that this might the agent with development code E6007. The association between example 9, E6007 and milategrast is speculative, provided in good faith, and will only be confirmed by open publication of name-to-structure by Esai.
iupac name: 1-(cyclopropylmethyl)-4-[2-(3,3,5,5-tetramethylcyclohexyl)phenyl]piperazine
synonym: example 9 [US20050261291A1]
approved: f
ligand name: milategrast
type: SyntheticOrganicLigand

imnopitant
in ch i key: HCNNJLLLMSVTFH-UHFFFAOYSA-N
in ch i: InChI=1S/C28H28F6N4O/c1-18-6-4-5-7-22(18)23-15-25(38-10-8-36(2)9-11-38)35-16-24(23)26(39)37(3)17-19-12-20(27(29,30)31)14-21(13-19)28(32,33)34/h4-7,12-16H,8-11,17H2,1-3H3
comment: Imnopitant (compound 20) is a neurokinin NK1 receptor antagonist that was identified in the same SAR study as <Ligand id=5742/> and <Ligand id=5759/> <Reference id=18860/>.
iupac name: N-[[3,5-bis(trifluoromethyl)phenyl]methyl]-N-methyl-4-(2-methylphenyl)-6-(4-methylpiperazin-1-yl)pyridine-3-carboxamide
xref: CHEMBL206488
synonym: compound 20 [PMID: 16332435]
approved: f
ligand name: imnopitant
type: SyntheticOrganicLigand

pamufetinib
in ch i key: ORRNXRYWGDUDOG-UHFFFAOYSA-N
in ch i: InChI=1S/C27H23FN4O4S/c1-29-26(34)19-14-18-21(15-24(19)35-2)30-11-10-22(18)36-23-9-8-17(13-20(23)28)31-27(37)32-25(33)12-16-6-4-3-5-7-16/h3-11,13-15H,12H2,1-2H3,(H,29,34)(H2,31,32,33,37)
comment: Pamufetinib (TAS-115) is a dual MET/VEGFR2(KDR) receptor tyrosine kinase inhibitor <Reference id=38196/>. It was designed by Taiho Pharmaceutical as a potential anticancer drug <Reference id=38195/>. It is a Type 1 ATP competitive inhibitor.
xref: CHEMBL3764045
synonym: TAS-115
synonym: TAS115
approved: f
ligand name: pamufetinib
type: SyntheticOrganicLigand

brepocitinib
in ch i key: BUWBRTXGQRBBHG-MJBXVCDLSA-N
in ch i: InChI=1S/C18H21F2N7O/c1-25-8-11(7-22-25)23-17-21-5-4-15(24-17)26-9-12-2-3-13(10-26)27(12)16(28)14-6-18(14,19)20/h4-5,7-8,12-14H,2-3,6,9-10H2,1H3,(H,21,23,24)/t12-,13+,14-/m0/s1
comment: Brepocitinib (PF-06700841) is a dual Janus kinase 1 (JAK1) and TYK2 inhibitor <Reference id=38194/>. It is proposed for treating autoimmune and other inflammatory conditions. Brepocitinib is a Type 1 ATP site inhibitor.
iupac name: [(1S)-2,2-difluorocyclopropyl]-[(1S,5R)-3-[2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]-3,8-diazabicyclo[3.2.1]octan-8-yl]methanone
synonym: PF-06700841
synonym: PF06700841
synonym: compound 23 [PMID: 30113844]
approved: f
ligand name: brepocitinib
type: SyntheticOrganicLigand

izencitinib
in ch i key: DADAEARVGOQWHV-ALOPSCKCSA-N
in ch i: InChI=1S/C22H26N8/c1-14-10-21(29-28-14)26-20-13-19-18(4-2-8-24-19)22(27-20)25-15-11-16-5-6-17(12-15)30(16)9-3-7-23/h2,4,8,10,13,15-17H,3,5-6,9,11-12H2,1H3,(H3,25,26,27,28,29)/t15?,16-,17+
comment: Izencitinib (TD-1473) is described as a Janus kinase (JAK) inhibitor in INN proposed list 121 (of August 2019). It is example 1 in Theravance Biopharma's patent that claims JAK inhibitors for immunomodulatory potential <Reference id=38193/>. Despite this 2020 article that describes preclinical development and early clinical evaluation of TD-1473 <Reference id=42602/>, the chemical structure remains undisclosed. TD-1473 is orally delivered, and was designed to be gut-selective in its action, for application in inflammatory bowel diseases.
iupac name: 3-[(1R,5S)-3-[[7-[(5-methyl-1H-pyrazol-3-yl)amino]-1,6-naphthyridin-5-yl]amino]-8-azabicyclo[3.2.1]octan-8-yl]propanenitrile
synonym: example 1 [WO2016191524A1]
synonym: TD-1473
synonym: TD1473
synonym: JNJ-8398
synonym: JNJ8398
approved: f
ligand name: izencitinib
type: SyntheticOrganicLigand

remibrutinib
in ch i key: CUABMPOJOBCXJI-UHFFFAOYSA-N
in ch i: InChI=1S/C27H27F2N5O3/c1-4-23(35)34(3)9-10-37-25-24(31-14-32-26(25)30)20-12-18(28)13-22(15(20)2)33-27(36)19-8-7-17(11-21(19)29)16-5-6-16/h4,7-8,11-14,16H,1,5-6,9-10H2,2-3H3,(H,33,36)(H2,30,31,32)
comment: Remibrutinib (LOU064) is one of the examples claimed in Novartis' patent WO2015079417A1 <Reference id=38192/>, for novel amino pyrimidine derivatives that act as Bruton's tyrosine kinase (BTK) inhibitors and which claims their potential to treat autoimmune disorders, inflammatory/allergic diseases, transplant rejection and cancers of hematopoietic origin or solid tumours. The formal chemical name (LOU064; remibrutinib) to structure disclosure was published in February 2020 <Reference id=38930/>. LOU064 is a covalent BTK inhibitor that binds the inactive conformation of the enzyme. This improves its selectivity compared to currently marketed covalent BTK inhibitors, and renders it more suitable for use in non-oncology indications.
iupac name: N-[3-[6-amino-5-[2-[methyl(prop-2-enoyl)amino]ethoxy]pyrimidin-4-yl]-5-fluoro-2-methylphenyl]-4-cyclopropyl-2-fluorobenzamide
synonym: example 6 [WO2015079417A1]
synonym: LOU-064
synonym: compound 25 [PMID: 32083858]
synonym: LOU064
approved: f
ligand name: remibrutinib
type: SyntheticOrganicLigand

zorifertinib
in ch i key: MXDSJQHFFDGFDK-CYBMUJFWSA-N
comment: Zorifertinib (AZD3759) is an investigational EGFR tyrosine kinase inhibitor <Reference id=38189/>. It is potent, orally active and brain-penetrant. AZD3759 was designed to target brain metastases in patients with advanced EGFR-driven lung cancer.
iupac name: [4-(3-chloro-2-fluoroanilino)-7-methoxyquinazolin-6-yl] (2R)-2,4-dimethylpiperazine-1-carboxylate
xref: CHEMBL3623290
synonym: AZD3759
synonym: AZD-3759
synonym: compound 1m [PMID: 26313252]
approved: f
ligand name: zorifertinib
type: SyntheticOrganicLigand

ractopamine
canonical SMILES: CC(NCC(c1ccc(cc1)O)O)CCc1ccc(cc1)O
isomeric SMILES: CC(NCC(c1ccc(cc1)O)O)CCc1ccc(cc1)O
in ch i key: YJQZYXCXBBCEAQ-UHFFFAOYSA-N
in ch i: InChI=1S/C18H23NO3/c1-13(2-3-14-4-8-16(20)9-5-14)19-12-18(22)15-6-10-17(21)11-7-15/h4-11,13,18-22H,2-3,12H2,1H3
comment: Ractopamine exhibits agonist activity at the trace amine receptor 1 (TA1) <Reference id=38181/> and β-adrenoceptors <Reference id=38182/><Reference id=38183/>. In some countries ractopamine is used as a feed additive in commercial livestock husbandry to increase lean meat mass. This use is banned in the EU and many other countries, but is permitted in countries including the US, Canada, Mexico, Japan and South Korea. Ractopamine's effect on human physiology has not been fully characterised, so the safety of consuming trace ractopamine in meat from treated animals remains controversial. Commercially used ractopamine is administered as the hydrochloride salt and is a racemic mixture of all 4 possible stereoenantiomers. We show the structure without specified stereochemistry to represent the mixture.
iupac name: 4-[3-[[2-hydroxy-2-(4-hydroxyphenyl)ethyl]amino]butyl]phenol
xref: CHEMBL509336
synonym: EL-737
synonym: ractopamin
synonym: Optaflexx®
synonym: Paylean®
synonym: Tomax®
approved: f
ligand name: ractopamine
type: SyntheticOrganicLigand

ulotaront
canonical SMILES: CNCC1OCCc2c1scc2
isomeric SMILES: CNC[C@@H]1OCCc2c1scc2
in ch i key: ABDDQTDRAHXHOC-QMMMGPOBSA-N
in ch i: InChI=1S/C9H13NOS/c1-10-6-8-9-7(2-4-11-8)3-5-12-9/h3,5,8,10H,2,4,6H2,1H3/t8-/m0/s1
comment: Ulotaront (SEP-363856) is an orally active and brain-penetrant psychotropic agent with a novel mechanism of action. It acts as a trace amine-associated receptor 1 (TAAR1) agonist with additional 5-HT1A receptor agonist activity, and agonism at both of these receptors appears to be required for its clinical effects <Reference id=38175/><Reference id=44138/>. SEP-363856 is being developed by Sunovion Pharmaceuticals and PsychoGenics, and was granted FDA Breakthrough Therapy Designation as an anti-schizophrenia therapeutic in May 2019. The lack of D2 receptor activity distinguishes SEP-363856 from current antipsychotic medications. In the Dedic et al. article from 2019 SEP-363856 refers to the hydrochloride salt. We show the parent molecule here. This S enantiomer is more active at TAAR1 compared to the R stereoenantiomer <Reference id=38175/>.
iupac name: 1-[(7S)-5,7-dihydro-4H-thieno[2,3-c]pyran-7-yl]-N-methylmethanamine
synonym: SEP-856
synonym: SEP363856
synonym: SEP-363856 (parent molecule)
synonym: example 129 [WO2011069063A2]
approved: f
ligand name: ulotaront
type: SyntheticOrganicLigand

CR4056
canonical SMILES: c1ccc(cc1)c1ncc2c(n1)ccc(c2)n1cncc1
isomeric SMILES: c1ccc(cc1)c1ncc2c(n1)ccc(c2)n1cncc1
in ch i key: CSZGXYBGYFNSCO-UHFFFAOYSA-N
in ch i: InChI=1S/C17H12N4/c1-2-4-13(5-3-1)17-19-11-14-10-15(6-7-16(14)20-17)21-9-8-18-12-21/h1-12H
comment: CR4056 is reported to bind imidazoline-binding sites known as imidazoline receptor I2 <Reference id=38173/>. It was developed by Rottapharm Biotech and is being pursued as a novel analgesic for inflammatory and neuropathic pain <Reference id=38171/><Reference id=38170/><Reference id=38172/>. Potential for efficacy in humans has been demonstrated in rodent models of nociceptive and neuropathic pain. To date (August 2019) clinical efficacy from a proof-of-concept study in patients with knee osteoarthritis pain has only been reported in meeting abstract form (see Rovati et al. Abstract Number: 1193, 2017 ACR/ARHP Annual Meeting). The associated trial registry number is EudraCT 2015-001136-37.
iupac name: 6-imidazol-1-yl-2-phenylquinazoline
xref: CHEMBL2179398
synonym: CR-4056
synonym: US8633208, 1
approved: f
ligand name: CR4056
type: SyntheticOrganicLigand

NMRA-140
in ch i key: CQOJHAJWCDJEAT-UHFFFAOYSA-N
in ch i: InChI=1S/C25H32FN5O2/c1-4-17-13-20-15(2)22(25-27-16(3)30-33-25)24(29-23(20)21(26)14-17)31-9-5-18(6-10-31)28-19-7-11-32-12-8-19/h13-14,18-19,28H,4-12H2,1-3H3
comment: NMRA-140 (formerly BTRX-335140, a.k.a. CYM-53093) is a selective κ opioid receptor antagonist <Reference id=38165/>. It has favourable drug-like properties in preclinical models, and is being proposed as a potential therapeutic for migraine <Reference id=38166/>, stress-related mood disorders (including depression), anxiety, and drug abuse. Neumora Therapeutics acquired BTRX-335140 in their buyout of Blackthorn Therapeutics.
iupac name: 1-[6-ethyl-8-fluoro-4-methyl-3-(3-methyl-1,2,4-oxadiazol-5-yl)quinolin-2-yl]-N-(oxan-4-yl)piperidin-4-amine
synonym: CYM-53093
synonym: CYM53093
synonym: BTRX335140
synonym: compound 58 [PMID: 30707578]
synonym: BTRX-335140
approved: f
ligand name: NMRA-140
type: SyntheticOrganicLigand

BPN14770
in ch i key: LTSUMTMGJHPGFX-UHFFFAOYSA-N
comment: BPN14770 is reported as a selective allosteric inhibitor of phosphodiesterase 4D (PDE4D) <Reference id=38161/>. BPN14770 achieves isotype selectivity by binding to a single amino acid difference on the UCR2 regulatory domain of PDE4D that controls access of cAMP substrate to the enzyme's catalytic site. Dimeric isoforms of PDE4D appear to be important for normal brain function <Reference id=38162/>, with abnormally/inappropriately active isoform dimers being associated with intellectual disability <Reference id=38163/>.
iupac name: 2-(4-{[2-(3-chlorophenyl)-6-(trifluoromethyl)pyridin-4-yl]methyl}phenyl)acetic acid
synonym: BPN-14770
synonym: BPN 14770
synonym: compound 28 [PMID: 31013090]
approved: f
ligand name: BPN14770
type: SyntheticOrganicLigand

compound 7 [PMID: 31381331]
canonical SMILES: [O-]C(=O)CC(c1cccc(c1)n1nc(cc1C)C)C[N+]1(C)CCC(C1)CCc1ccc2c(n1)NCCC2
in ch i key: BXOSGYRJKCYDLH-YAYCEGLDSA-N
in ch i: InChI=1S/C30H39N5O2/c1-21-16-22(2)34(33-21)28-8-4-6-25(17-28)26(18-29(36)37)20-35(3)15-13-23(19-35)9-11-27-12-10-24-7-5-14-31-30(24)32-27/h4,6,8,10,12,16-17,23,26H,5,7,9,11,13-15,18-20H2,1-3H3,(H-,31,32,36,37)/t23-,26-,35+/m1/s1
comment: Compound 7 selectively inhibits αVβ6 integrin-mediated cell adhesion <Reference id=38142/>. It was discovered in a medicinal chemistry effort to rationally design improved therapeutics for idiopathic pulmonary fibrosis (IPF). Docking studies indicate that compound 7 binds in a pocket formed at the interface of the α and β integrin subunits. Since compound 7 is selective for β6-containing αV integrins we have recorded the binding data against the various β subunits tested, to make comparisons clearer.
iupac name: (3S)-3-(3-(3,5-Dimethyl-1H-pyrazol-1-yl)phenyl)-4-((1S,3R)-1-methyl-3-(2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethyl)pyrrolidin-1-ium-1-yl)butanoate
approved: f
ligand name: compound 7 [PMID: 31381331]
type: SyntheticOrganicLigand

Example 4 [WO2017202275A1]
in ch i key: YYAPLXNCTNGBJO-LJAQVGFWSA-N
comment: Example 4 is a highly potent, small-molecule inhibitor of the PD-1/PD-L1 interaction that is claimed in patent WO2017202275A1 <Reference id=38139/>.
iupac name: (2S)-1-{[4-({2-bromo-[1,1'-biphenyl]-3-yl}methoxy)-5-chloro-2-[(2-cyanopyridin-4-yl)methoxy]phenyl]methyl}piperidine-2-carboxylic acid
approved: f
ligand name: Example 4 [WO2017202275A1]
type: SyntheticOrganicLigand

compound 9 [Kumar et al., 2019]
canonical SMILES: CC(=O)N(c1ccc(cc1)Cl)C1=CC(=O)CCC1
isomeric SMILES: CC(=O)N(c1ccc(cc1)Cl)C1=CC(=O)CCC1
in ch i key: UOYMKJRPIIMBTR-UHFFFAOYSA-N
in ch i: InChI=1S/C14H14ClNO2/c1-10(17)16(12-7-5-11(15)6-8-12)13-3-2-4-14(18)9-13/h5-9H,2-4H2,1H3
comment: Compound 9 is an example of a new chemotype (with a cyclic enaminone structural scaffold) for selective COX2 inhibitors (COXIBs) <Reference id=38137/>. It is hoped that this new chemotype will be devoid of the side effects related to the sulfonamide/sulfonate group common in existing COXIB drugs, and thus lead the way to overcoming the adverse cardiovascular effects that have led to the withdrawl of some existing COXIBs from use in the clinic (<Ligand id=2893/> and <Ligand id=2894/>).
iupac name: N-(4-Chlorophenyl)-N-(3-oxo-cyclohex-1-enyl)acetamide
approved: f
ligand name: compound 9 [Kumar et al., 2019]
type: SyntheticOrganicLigand

LUF7244
in ch i key: KKKJYDOHVKIIQP-UHFFFAOYSA-N
in ch i: InChI=1S/C20H15ClN2O3/c21-16-4-1-3-15(11-16)20(25)14-6-8-18(9-7-14)26-13-19(24)23-17-5-2-10-22-12-17/h1-12H,13H2,(H,23,24)
comment: LUF7244 is a negative allosteric modulator (NAM) of orthosteric ligand binding to the hERG channel (Kv11.1) <Reference id=38135/>. It was used to test the hypothesis that hERG NAMs might be able to counteract the proarrhythmic effects of hERG-blocking drugs. Using <Ligand id=2604/> as a known hERG orthosteric channel blocker, LUF7244 has been shown to protect against dofetilide‐induced early after depolarizations (EADs) in vitro and dofetilide‐induced TdP arrhythmia in vivo <Reference id=38136/>. It has been proposed that hERG NAMs might find therapeutic potential to alleviate long QTs caused by hERG-blocking drugs, and/or to treat patients with congential long QT syndromes that are associated with Kv11.1 and Kv7.1 channels.
iupac name: 2-[4-(3-chlorobenzoyl)phenoxy]-N-(pyridin-3-yl)acetamide
xref: CHEMBL3740151
synonym: compound 7i [PMID: 26519929]
approved: f
ligand name: LUF7244
type: SyntheticOrganicLigand

avitriptan
in ch i key: WRZVGHXUPBWIOO-UHFFFAOYSA-N
in ch i: InChI=1S/C22H30N6O3S/c1-23-32(29,30)15-17-5-6-20-19(12-17)18(13-25-20)4-3-7-27-8-10-28(11-9-27)22-21(31-2)14-24-16-26-22/h5-6,12-14,16,23,25H,3-4,7-11,15H2,1-2H3
comment: Avitriptan (BMS-180048) is a serotonin receptor agonist with selectivity for the 5-HT1D and 5-HT1B subtypes <Reference id=38129/>. It was investigated as an anti-mirgaine agent in the late 1990s <Reference id=38130/><Reference id=38131/><Reference id=38132/><Reference id=38133/> but never reached the market.
xref: CHEMBL2110755
synonym: BMS-180048
synonym: BMS-180,048
synonym: BMS180048
approved: f
ligand name: avitriptan
type: SyntheticOrganicLigand

compound 23 [PMID: 31398032]
in ch i key: CDJMQOCUCVPNIU-UHFFFAOYSA-N
comment: Compound 23 the most potent inhibitor of the bromodomain-containing enzyme ATAD2 to be identified using a specially designed high-throughput screening and hit qualification process <Reference id=38128/>. The compound exhibits a novel binding mode for bromodomain inhibitors that includes displacement of all of the conserved water molecules, and formation of a halogen-bonding interaction, within the active site.
iupac name: N-(4-Bromo-3-(piperidin-1-ylsulfonyl)phenyl)-2-(4-cyclopropyl-4-methyl-2,5-dioxoimidazolidin-1-yl)acetamide
approved: f
ligand name: compound 23 [PMID: 31398032]
type: SyntheticOrganicLigand

compound 10 [PMID: 31306001]
canonical SMILES: COC(=O)c1cccc(c1)CSc1nc(N)c(c(c1C#N)c1ccco1)C#N
isomeric SMILES: COC(=O)c1cccc(c1)CSc1nc(N)c(c(c1C#N)c1ccco1)C#N
in ch i key: IKBOAPCYYHRBSI-UHFFFAOYSA-N
in ch i: InChI=1S/C20H14N4O3S/c1-26-20(25)13-5-2-4-12(8-13)11-28-19-15(10-22)17(16-6-3-7-27-16)14(9-21)18(23)24-19/h2-8H,11H2,1H3,(H2,23,24)
comment: Compound 10 is a modulator of adenosine receptor (AR) activity. It acts as a dual adenosine A1R inverse agonist/A2A/2BR antagonist <Reference id=38121/>. The compound exhibits favourable half-life values in rat and human plasma (≥240 min in both species) and is orally bioavailable.
iupac name: Methyl 3-(((6-Amino-3,5-dicyano-4-(furan-2-yl)pyridin-2-yl)sulfanyl)methyl)benzoate
approved: f
ligand name: compound 10 [PMID: 31306001]
type: SyntheticOrganicLigand

UDM-001651
in ch i key: LFOIDLOIBZFWDO-UHFFFAOYSA-N
in ch i: InChI=1S/C28H23N3O5S/c1-32-21-12-24(35-17-19-9-6-10-20(11-19)34-16-18-7-4-3-5-8-18)22-14-26(36-25(22)13-21)23-15-31-27(29-23)37-28(30-31)33-2/h3-15H,16-17H2,1-2H3
comment: UDM-001651 is a potent, selective, and orally bioavailable antagonist of protease-activated receptor 4 (PAR4) <Reference id=38119/>. It was used to validate PAR4 antagonism as a potential antithrombotic mechanism, and is a suitable tool to further this proposed utility. Based on the chemical structure ChEMBL has activity data for this compound that has been extracted from patent WO2013163279A1 from Bristol-Myers Squibb and the Université de Montréal <Reference id=38120/>.
xref: CHEMBL3728620
synonym: compound 54 [PMID: 31246024]
approved: f
ligand name: UDM-001651
type: SyntheticOrganicLigand

compound 5d [PMID: 31335136]
in ch i key: CPUXOJVJEJZOSP-UHFFFAOYSA-N
comment: Compound 5d is a potent, 4-methylquinazoline-based pan-PI3K inhibitor <Reference id=38117/>. It is one of the examples claimed in patent WO2018121550A1 from the Institute of Pharmaceutical Research, Chinese Academy of Medical Sciences <Reference id=38118/>.
iupac name: 2,4-difluoro-N-[2-methoxy-5-[4-methyl-8-[(3-methyloxetan-3-yl)methoxy]quinazolin-6-yl]pyridin-3-yl]benzenesulfonamide
synonym: Example 59 [WO2018121550]
approved: f
ligand name: compound 5d [PMID: 31335136]
type: SyntheticOrganicLigand

MS48107
in ch i key: KKHDNAZPEMYUNO-UHFFFAOYSA-N
in ch i: InChI=1S/C23H20FN5O2/c24-19-8-4-5-16(14-30)20(19)21-27-22(25)29-23(28-21)26-13-15-9-11-18(12-10-15)31-17-6-2-1-3-7-17/h1-12,30H,13-14H2,(H3,25,26,27,28,29)
comment: MS48107 is a potent and selective positive allosteric modulator (PAM) of the proton-sensing orphan GPCR, GPR68 <Reference id=38089/>. It was discovered via a SAR study based on the scaffold of the first reported GPR68 PAM, <Ligand id=9155/>. MS48107 allosterically increases proton affinity (α-cooperativity) for GPR68. The compound is bioavailable and brain-penetrant in mice, and these attributes in conjunction with its selectivity presents a novel in vitro and in vivo tool that is suitable for investigating the physiological and pathophysiological roles of GPR68.
iupac name: (2-(4-Amino-6-((4-phenoxybenzyl)amino)-1,3,5-triazin-2-yl)-3-fluorophenyl)methanol
synonym: GPR68 α-PAM 71
synonym: compound 71 [PMID: 31298539]
approved: f
ligand name: MS48107
type: SyntheticOrganicLigand

darolutamide
in ch i key: BLIJXOOIHRSQRB-PXYINDEMSA-N
in ch i: InChI=1S/C19H19ClN6O2/c1-11(22-19(28)18-8-17(12(2)27)23-24-18)10-26-6-5-16(25-26)13-3-4-14(9-21)15(20)7-13/h3-8,11-12,27H,10H2,1-2H3,(H,22,28)(H,23,24)/t11-,12?/m0/s1
comment: Darolutamide is a nonsteroidal, potent and selective antagonist of the androgen receptor (antiandrogen) <Reference id=38083/><Reference id=38084/>. It is able to overcome resistance to current nonsteroidal androgen receptor-targeted therapies (<Ligand id=6812/> and <Ligand id=9043/>). Darolutamide was developed by Orion and Bayer HealthCare.
iupac name: N-[(2S)-1-[3-(3-chloro-4-cyanophenyl)pyrazol-1-yl]propan-2-yl]-5-(1-hydroxyethyl)-1H-pyrazole-3-carboxamide
synonym: ODM-201
synonym: ODM201
synonym: BAY-1841788)
synonym: BAY1841788
synonym: example 56 [US9657003]
synonym: Nubeqa®
approved: t
ligand name: darolutamide
type: SyntheticOrganicLigand

compound 24 [PMID: 31343176]
in ch i key: CHVVDDGGNOHSOG-UHFFFAOYSA-N
comment: Compound 24 is reported as a selective, potent and orally active inhibitor of 17β-HSD2 (HSD17B2) <Reference id=38074/>. It effectively preserves bone structure in a rat model of ovariectomy-induced osteoporosis.
iupac name: 4-Fluoro-N-(2-(5-(2,4,5-trifluoro-3-hydroxybenzoyl)thiophen-2-yl)phenyl)benzene-sulfonamide
approved: f
ligand name: compound 24 [PMID: 31343176]
type: SyntheticOrganicLigand

compound E22 [PMID: 31298542]
in ch i key: SXDPQGRNHSLZPC-ZJNRKIDTSA-N
comment: Compound E22 is a pan-Akt (protein kinase B) inhibitor that was designed to combine anti-tumour efficacy with favourable drug-like properties <Reference id=38073/>.
iupac name: 5-Chloro-4-(4-chloro-1-methyl-1H-pyrazol-5-yl)-N-((3S,4S,6S)-4-(3,4-difluorophenyl)-6-(2-(methylamino)-2-oxoethyl)piperidin-3-yl)furan-2-carboxamide
approved: f
ligand name: compound E22 [PMID: 31298542]
type: SyntheticOrganicLigand

trequinsin
in ch i key: MCMSJVMUSBZUCN-UHFFFAOYSA-N
in ch i: InChI=1S/C24H27N3O3/c1-14-9-15(2)23(16(3)10-14)25-22-13-19-18-12-21(30-6)20(29-5)11-17(18)7-8-27(19)24(28)26(22)4/h9-13H,7-8H2,1-6H3
comment: Trequinsin is a nonselective phosphodiesterase inhibitor that produces an antihypertensive vasodilator effect in vivo <Reference id=38068/>. It also inhibits induced platelet aggregation in vitro <Reference id=38069/>
iupac name: 9,10-dimethoxy-3-methyl-2-(2,4,6-trimethylphenyl)imino-6,7-dihydropyrimido[4,3-a]isoquinolin-4-one
xref: CHEMBL285913
synonym: HL 725
synonym: compound 56b [PMID: 6492077]
approved: f
ligand name: trequinsin
type: SyntheticOrganicLigand

compound 10a [PMID: 31283223]
canonical SMILES: CCCCc1nn2c(c1)c(N)nc1c2cccc1
isomeric SMILES: CCCCc1nn2c(c1)c(N)nc1c2cccc1
in ch i key: YMNPLUINBRDMEW-UHFFFAOYSA-N
in ch i: InChI=1S/C14H16N4/c1-2-3-6-10-9-13-14(15)16-11-7-4-5-8-12(11)18(13)17-10/h4-5,7-9H,2-3,6H2,1H3,(H2,15,16)
comment: Compound 10a is the most potent in a series of molecules designed to identify novel selective Toll-like receptor 7 (TLR7) antagonists <Reference id=38067/>.
iupac name: 2-butylpyrazolo[1,5-a]quinoxalin-4-amine
approved: f
ligand name: compound 10a [PMID: 31283223]
type: SyntheticOrganicLigand

compound 5b [PMID: 31287314]
canonical SMILES: [O]#C[Co]1(C#[O])(C#[O])C2C1([Co]2(C#[O])(C#[O])C#[O])CNc1ccc(cc1)S(=O)(=O)N
isomeric SMILES: [O]#C[Co]1(C#[O])(C#[O])C2C1([Co]2(C#[O])(C#[O])C#[O])CNc1ccc(cc1)S(=O)(=O)N
in ch i key: QMTFSGDBEOQNOF-UHFFFAOYSA-N
in ch i: InChI=1S/C9H10N2O2S.6CO.2Co/c1-2-7-11-8-3-5-9(6-4-8)14(10,12)13;6*1-2;;/h1,3-6,11H,7H2,(H2,10,12,13);;;;;;;;
comment: Compound 5b is a hybrid molecule that contains carbonic anhydrase inhibitor <Ligand id=10433/>, attached to a carbon monoxide (CO) releasing molecule (CORM) <Reference id=38066/>.
approved: f
ligand name: compound 5b [PMID: 31287314]
type: SyntheticOrganicLigand

compound 5a [PMID: 31287314]
canonical SMILES: C#CCNc1ccc(cc1)S(=O)(=O)N
isomeric SMILES: C#CCNc1ccc(cc1)S(=O)(=O)N
in ch i key: HPRYFTLQNXBKDM-UHFFFAOYSA-N
in ch i: InChI=1S/C9H10N2O2S/c1-2-7-11-8-3-5-9(6-4-8)14(10,12)13/h1,3-6,11H,7H2,(H2,10,12,13)
comment: Compound 5a is a carbonic anhydrase inhibitor <Reference id=38066/>. It is the parent molecule of <Ligand id=10434/>, which has a carbon monoxide (CO) releasing molecule (CORM) attached via a linker.
iupac name: 4-(prop-2-ynylamino)benzenesulfonamide
approved: f
ligand name: compound 5a [PMID: 31287314]
type: SyntheticOrganicLigand

deucravacitinib
in ch i key: BZZKEPGENYLQSC-FIBGUPNXSA-N
in ch i: InChI=1S/C20H22N8O3/c1-21-20(30)16-14(9-15(25-26-16)24-19(29)11-7-8-11)23-13-6-4-5-12(17(13)31-3)18-22-10-28(2)27-18/h4-6,9-11H,7-8H2,1-3H3,(H,21,30)(H2,23,24,25,29)/i1D3
comment: Deucravacitinib (BMS-986165) is a selective, orally active, allosteric inhibitor of the Janus kinase family enzyme, tyrosine kinase 2 (TYK2) <Reference id=38065/><Reference id=38441/>. The deuteromethyl amide group confers selectivity by virtue of binding to a pocket in the TYK2 JH2 pseudokinase domain.
iupac name: 6-(cyclopropanecarbonylamino)-4-[2-methoxy-3-(1-methyl-1,2,4-triazol-3-yl)anilino]-N-(trideuteriomethyl)pyridazine-3-carboxamide
synonym: BMS986165
synonym: compound 11 [PMID: 31318208}
synonym: Tyk2-IN-4
synonym: BMS-986165
synonym: Sotyktu®
approved: t
ligand name: deucravacitinib
type: SyntheticOrganicLigand

E-52862
canonical SMILES: Cc1cc(nn1c1ccc2c(c1)cccc2)OCCN1CCOCC1
isomeric SMILES: Cc1cc(nn1c1ccc2c(c1)cccc2)OCCN1CCOCC1
in ch i key: DGPGXHRHNRYVDH-UHFFFAOYSA-N
in ch i: InChI=1S/C20H23N3O2/c1-16-14-20(25-13-10-22-8-11-24-12-9-22)21-23(16)19-7-6-17-4-2-3-5-18(17)15-19/h2-7,14-15H,8-13H2,1H3
comment: E-52862 is a σ1 receptor antagonist <Reference id=38049/>. It has been shown to exert dose-dependent antinociceptive effects in several neuropathic pain models.
iupac name: 4-[2-(5-methyl-1-naphthalen-2-ylpyrazol-3-yl)oxyethyl]morpholine
xref: CHEMBL2170062
synonym: E52862
synonym: sigma 1 receptor antagonist (S1RA)
synonym: MR309
synonym: compound 28 [PMID: 22784008]
approved: f
ligand name: E-52862
type: SyntheticOrganicLigand

GS-444217
in ch i key: ZGCMQKWOUIMBEP-UHFFFAOYSA-N
in ch i: InChI=1S/C23H21N7O/c31-23(20-11-19(8-9-24-20)29-12-21(25-13-29)15-4-5-15)27-17-3-1-2-16(10-17)22-28-26-14-30(22)18-6-7-18/h1-3,8-15,18H,4-7H2,(H,27,31)
comment: GS-444217 is an orally active and selective inhibitor of apoptosis signal-regulating kinase 1 (ASK1; MAP3K5) that was designed by Gilead Sciences. It has anti-fibrotic activity that is mediated via downstream inhibition of p38 MAP kinase pathway activation <Reference id=38041/>.
iupac name: 4-(4-cyclopropylimidazol-1-yl)-N-[3-(4-cyclopropyl-1,2,4-triazol-3-yl)phenyl]pyridine-2-carboxamide
approved: f
ligand name: GS-444217
type: SyntheticOrganicLigand

J30-8
isomeric SMILES: Fc1ccc2c(c1)/C(=C/1/S/C(=N/c3ccccc3Cl)/NC1=O)/C(=O)N2
in ch i key: HNOFQKYBQYGFNQ-YPKPFQOOSA-N
comment: J30-8 is a selective JNK3 (a.k.a. mitogen-activated protein kinase 10; MAPK10) inhibitor. It is the most potent inhibitor from a series of compounds reported by Dou et al. (2019) that were identified using structure-based virtual, similarity and SAR screening stages <Reference id=38036/>. JNK3 has been proposed as the primary kinase that is responsible for phosphorylating Aβ precursor protein (APP) at Thr668, which leads to accelerated Aβ formation and elevated plaque burden <Reference id=38037/><Reference id=38038/>. Pharmacological inhibition of JNK3 is therefore being explored as a novel modality for the treatment of Alzheimer's and other neurodegenerative diseases. J30-8 provides a suitable in vitro and in vivo tool to further study JNK3's role in these pathological conditions.
iupac name: 3-[(2Z,5Z)-2-[(2-chlorophenyl)imino]-4-oxo-1,3-thiazolidin-5-ylidene]-5-fluoro-2,3-dihydro-1H-indol-2-one
approved: f
ligand name: J30-8
type: SyntheticOrganicLigand

compound 25 [PMID: 31260299]
in ch i key: RFCJOYPMBVRHBV-UHFFFAOYSA-N
in ch i: InChI=1S/C18H14FN5O2/c1-26-14-4-8-6-23-24-13(8)5-10(14)9-2-3-12(19)15-16(20)11(18(21)25)7-22-17(9)15/h2-7H,1H3,(H2,20,22)(H2,21,25)(H,23,24)
comment: Compound 25 is a potent, selective and reversible inhibitor of Bruton's tyrosine kinase (BTK) <Reference id=38035/>. It is built on a 4-aminoquinoline scaffold, and has improved drug-like properties (aqueous solubility, potency and stability) compared to previously reported cinnoline scaffold compounds <Reference id=38034/>.
iupac name: 4-Amino-5-fluoro-8-(5-methoxy-1H-indazol-6-yl)quinoline-3-carboxamide
approved: f
ligand name: compound 25 [PMID: 31260299]
type: SyntheticOrganicLigand

basmisanil
in ch i key: VCGRFBXVSFAGGA-UHFFFAOYSA-N
in ch i: InChI=1S/C21H20FN3O5S/c1-14-18(20(24-30-14)15-2-5-17(22)6-3-15)13-29-19-7-4-16(12-23-19)21(26)25-8-10-31(27,28)11-9-25/h2-7,12H,8-11,13H2,1H3
comment: Basmisanil (RG1662) is a small molecule negative allosteric modulator that is selective for gamma-aminobutyric acid (GABA) A receptors alpha 5, GABRA5, which are expressed in discrete brain regions that are associated with cognitive processing <Reference id=38033/>. It has been proposed for rescuing learning/memory deficits in individuals with intellectual disabilities such as those associated with Down syndrome <Reference id=38032/>. RG1662 has also been described as an inverse agonist of the α5subunit-containing GABAA receptors.
iupac name: (1,1-dioxo-1,4-thiazinan-4-yl)-[6-[[3-(4-fluorophenyl)-5-methyl-1,2-oxazol-4-yl]methoxy]pyridin-3-yl]methanone
xref: CHEMBL3681419
synonym: example 112 [WO2009071476]
synonym: RG-1662
synonym: RG1662
approved: f
ligand name: basmisanil
type: SyntheticOrganicLigand

tryptanthrin
canonical SMILES: O=C1c2nc3ccccc3c(=O)n2c2c1cccc2
isomeric SMILES: O=C1c2nc3ccccc3c(=O)n2c2c1cccc2
in ch i key: VQQVWGVXDIPORV-UHFFFAOYSA-N
in ch i: InChI=1S/C15H8N2O2/c18-13-10-6-2-4-8-12(10)17-14(13)16-11-7-3-1-5-9(11)15(17)19/h1-8H
comment: Tryptanthrin acts as an inhibitor of indoleamine 2,3-dioxygenase 1 (IDO1) <Reference id=27057/>. Tryptanthrin is found in plants used in traditional Chinese medicine (Persicaria tinctorium and Isatis tinctoria).
iupac name: Indolo[2,1-b]quinazoline-6,12-dione
xref: CHEMBL306946
synonym: GNF-PF-2691
synonym: couroupitine a
approved: f
ligand name: tryptanthrin
type: NaturalProductLigand

PF-06873600
in ch i key: QIEKHLDZKRQLLN-FOIQADDNSA-N
comment: PF-06873600 <Reference id=42569/> is claimed as example 10 in patent WO2018033815. It is an orally bioavailable CDK2/4/6 inhibitor with antineoplastic potential <Reference id=37948/>.
iupac name: 6-(difluoromethyl)-8-[(1R,2R)-2-hydroxy-2-methylcyclopentyl]-2-[(1-methylsulfonylpiperidin-4-yl)amino]pyrido[2,3-d]pyrimidin-7-one
synonym: example 10 [WO2018033815]
synonym: PF06873600
approved: f
ligand name: PF-06873600
type: SyntheticOrganicLigand

ROCK inhibitor 3
canonical SMILES: COc1nc(NC2CCC(CC2)N)c(cc1C(=O)N)F
in ch i key: IMZIJLMIOSQRGE-ZKCHVHJHSA-N
in ch i: InChI=1S/C13H19FN4O2/c1-20-13-9(11(16)19)6-10(14)12(18-13)17-8-4-2-7(15)3-5-8/h6-8H,2-5,15H2,1H3,(H2,16,19)(H,17,18)/t7-,8-
comment: Inhibitor 3 is a selectve and potent inhibitor of the Rho-associated kinases, ROCK1 and ROCK2. The chemical structure presented here was drawn from Cantoni et al., 2019 <Reference id=37944/>. PubChem CID 46182713 presents the compound without specified stereochemistry.
iupac name: 5-fluoro-2-methoxy-6-{[(1r,4r)-4-aminocyclohexyl]amino}pyridine-3-carboxamide
synonym: Chiesi Rock inhibitor
synonym: example 3 [WO2010032875A2]
approved: f
ligand name: ROCK inhibitor 3
type: SyntheticOrganicLigand

VU0422288
canonical SMILES: Clc1ccc(nc1)Oc1ccc(cc1Cl)NC(=O)c1ccccn1
isomeric SMILES: Clc1ccc(nc1)Oc1ccc(cc1Cl)NC(=O)c1ccccn1
in ch i key: MZRLPXFGQKQHST-UHFFFAOYSA-N
comment: Group III mGlu receptor positive allosteric modulator.
iupac name: N-{3-chloro-4-[(5-chloropyridin-2-yl)oxy]phenyl}pyridine-2-carboxamide
synonym: VU-0422288
synonym: VU 0422288
synonym: ML396
synonym: ML-396
synonym: ML 396
approved: f
ligand name: VU0422288
type: SyntheticOrganicLigand

HSD1590
in ch i key: WTZMCUOBQPTERK-UHFFFAOYSA-N
in ch i: InChI=1S/C20H18BN3O3/c1-27-20-13(6-3-7-15(20)21(25)26)19-12-5-2-4-11(12)18-14-10-22-24-16(14)8-9-17(18)23-19/h3,6-10,25-26H,2,4-5H2,1H3,(H,22,24)
comment: HSD1590 is a boronic acid-containing Rho-associated kinase (ROCK) inhibitor <Reference id=37943/>. In vitro, it is more potent than <Ligand id=9322/> at binding to or inhibiting ROCK enzymatic activities.
approved: f
ligand name: HSD1590
type: SyntheticOrganicLigand

ripasudil
canonical SMILES: CC1CNCCCN1S(=O)(=O)c1cccc2c1c(F)cnc2
in ch i key: QSKQVZWVLOIIEV-NSHDSACASA-N
in ch i: InChI=1S/C15H18FN3O2S/c1-11-8-17-6-3-7-19(11)22(20,21)14-5-2-4-12-9-18-10-13(16)15(12)14/h2,4-5,9-11,17H,3,6-8H2,1H3/t11-/m0/s1
comment: Ripasudil is an isoquinoline class Rho-associated kinase (ROCK) inhibitor <Reference id=37941/><Reference id=37942/>. We present the parent molecule here. The hydrochloride dihydrate is referred to using the research code K-115 (see PubChem CID 11625386).
iupac name: 4-fluoro-5-[[(2S)-2-methyl-1,4-diazepan-1-yl]sulfonyl]isoquinoline
xref: CHEMBL3426621
synonym: K-115 (ripasudil hydrochloride dihydrate)
synonym: Glanatec®
synonym: K115
approved: t
ligand name: ripasudil
type: SyntheticOrganicLigand

fezolinetant
in ch i key: PPSNFPASKFYPMN-SECBINFHSA-N
in ch i: InChI=1S/C16H15FN6OS/c1-9-13-19-20-14(15-18-10(2)21-25-15)23(13)8-7-22(9)16(24)11-3-5-12(17)6-4-11/h3-6,9H,7-8H2,1-2H3/t9-/m1/s1
comment: Fezolinetant (ESN364) is a potent and selective neurokinin (NK) receptor 3 antagonist <Reference id=37938/>. It is being developed by Astellas Pharma as a non-hormonal therapeutic option for the treatment of sex-hormone disorders such as polycystic ovary syndrome <Reference id=43837/> and uterine fibroids, and for the management of the vasomotor symptoms that drive menopausal hot flashes <Reference id=43838/>.
iupac name: (4-fluorophenyl)-[(8R)-8-methyl-3-(3-methyl-1,2,4-thiadiazol-5-yl)-6,8-dihydro-5H-[1,2,4]triazolo[4,3-a]pyrazin-7-yl]methanone
xref: CHEMBL3608680
synonym: ESN364
synonym: compound 3 [PMID:26191358]
synonym: ESN-364
approved: f
ligand name: fezolinetant
type: SyntheticOrganicLigand

AM237
in ch i key: UNQYAAAWKOOBFQ-UHFFFAOYSA-N
comment: AM237 is a potent and selective TRPC5 channel activator <Reference id=37932/>. It is an analogue of the TRPC1/4/5 channel inhibitor <Ligand id=10291/>. Whilst AM237 activates homomeric TRPC5 channels it inhibits other TRPC1/4/5 channels, and is proposed as a useful chemical tool to help investigate TRPC1/4/5 channel composition and the biological functions of specific channels in different cells and/or tissues. It is orally bioavailable and suitable for in vivo studies. AM237 is one of the xanthine derivatives claimed in patent WO2014143799A2 <Reference id=37931/>.
iupac name: 7-[(4-chlorophenyl)methyl]-8-[4-chloro-3-(trifluoromethoxy)phenoxy]-1-(3-hydroxypropyl)-3-methylpurine-2,6-dione
synonym: Example 319 [WO2014143799]
approved: f
ligand name: AM237
type: SyntheticOrganicLigand

CHMFL-KIT-64
in ch i key: YOHLRCOPRAVUCJ-UHFFFAOYSA-N
comment: CHMFL-KIT-64 is a potent and orally available inhibitor of wild-type c-KIT and a range of known c-KIT resistance mutants <Reference id=37930/>. It has demonstrated anti-tumour efficacy in vitro, in mouse xenograft models, and against imatinib-resistant patient tumour cells expressing wild-type c-KIT. It has been proposed as a potential clinical lead for gastrointestinal stromal tumour (GIST) therapy as the majority (80-85%) of GISTs harbour c-KIT activation mutations. Other c-KIT mutations confer primary or secondary (acquired) resistance to <Ligand id=5687/> which is the first line drug used to combat GISTs. CHMFL-KIT-64 was designed to target mutations that are refractory to currently approved therapeutics including imatinib, <Ligand id=5713/> and <Ligand id=5891/>. It can potently inhibit the T670I ATP binding pocket (gatekeeper) mutant that is resistant to many other c-KIT inhibitors.
iupac name: 2-(4-Chloro-3-(trifluoromethyl)phenyl)-N-(4-((6,7-dimethoxyquinolin-4-yl)oxy)phenyl)acetamide
synonym: compound 18 [PMID: 31250638]
approved: f
ligand name: CHMFL-KIT-64
type: SyntheticOrganicLigand

RIPK2 inhibitor 5
in ch i key: UHDOJINBFLDQJM-UHFFFAOYSA-N
in ch i: InChI=1S/C21H22N4O4S2/c1-21(2,3)31(27,28)19-9-14-15(10-17(19)29-7-6-26)22-11-23-20(14)25-13-4-5-18-16(8-13)24-12-30-18/h4-5,8-12,26H,6-7H2,1-3H3,(H,22,23,25)
comment: This compound is a selective inhibitor of receptor interacting serine/threonine kinase 2 (RIPK2) <Reference id=37924/><Reference id=37925/>. It is the active metabolite of the phosphate ester prodrug <Ligand id=10413/>.
iupac name: 2-[4-(1,3-benzothiazol-5-ylamino)-6-tert-butylsulfonylquinazolin-7-yl]oxyethanol
synonym: compound 5 [PMID: 31265286]
approved: f
ligand name: RIPK2 inhibitor 5
type: SyntheticOrganicLigand

compound 49c [PMID: 29074775]
in ch i key: NCNJHAHPOUUEQX-LDVROUIZSA-N
in ch i: InChI=1S/C31H38N4O3/c1-23(25-11-7-4-8-12-25)32-22-29(36)28(21-24-9-5-3-6-10-24)33-30(37)26-13-15-27(16-14-26)31(38)35-19-17-34(2)18-20-35/h3-16,23,28-29,32,36H,17-22H2,1-2H3,(H,33,37)/t23-,28+,29-/m1/s1
comment: Compound 49c is a hydroxyl-ethyl-amine-based scaffold compound with antimalarial activity <Reference id=43248/>. We have drawn the structure as depicted in Pino et al. (2017) <Reference id=37922/>, with the indicated stereochemistry (but note that the IUPAC they provide is for the flat structure that is represented by PubChem CID 11619556). The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
iupac name: N-[(2S,3R)-3-Hydroxy-1-phenyl-4-[[(1R)-1-phenylethyl]amino]butan-2-yl]-4-(4-methylpiperazine-1-carbonyl)benzamide
xref: CHEMBL2334045
approved: f
ligand name: compound 49c [PMID: 29074775]
type: SyntheticOrganicLigand

compound 31 [PMID: 31259550]
in ch i key: KQZLRWGGWXJPOS-NLFPWZOASA-N
in ch i: InChI=1S/C26H28Cl2N6O/c1-15-10-17(5-8-24(15)33-9-3-4-19(33)14-35)23-13-30-25-22(12-29)32-34(26(25)31-23)16(2)20-7-6-18(27)11-21(20)28/h5-7,11,13,15-16,19,24,35H,3-4,8-10,14H2,1-2H3/t15-,16-,19+,24+/m1/s1
comment: Compound 31 is a selective antagonist of CCR4 <Reference id=37920/>.
iupac name: 1-[(1R)-1-(2,4-Dichlorophenyl)ethyl]-6-[(4S,5R)-4-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]-5-methylcyclohexen-1-yl]pyrazolo[3,4-b]pyrazine-3-carbonitrile
approved: f
ligand name: compound 31 [PMID: 31259550]
type: SyntheticOrganicLigand

GSK2239633A
in ch i key: YTEVTHHGQMUPHC-UHFFFAOYSA-N
comment: GSK2239633A is a arylsulfonamide class CC-chemokine receptor 4 (CCR4) antagonist. It binds the intracellular domain of the receptor, and therefore has an allosteric mode of action <Reference id=37918/>.
iupac name: N-[[3-[[3-[(5-chlorothiophen-2-yl)sulfonylamino]-4-methoxyindazol-1-yl]methyl]phenyl]methyl]-2-hydroxy-2-methylpropanamide
xref: CHEMBL2018969
synonym: compound 6 [PMID: 23409871]
synonym: GSK-2239633A
approved: f
ligand name: GSK2239633A
type: SyntheticOrganicLigand

PA21A092
in ch i key: AXHVMTZWSKDPRR-UHFFFAOYSA-N
in ch i: InChI=1S/C23H23ClFN5O/c1-13(2)22-26-18-7-5-6-8-19(18)30(22)12-20(31)27-23-21(14(3)28-29(23)4)16-10-9-15(24)11-17(16)25/h5-11,13H,12H2,1-4H3,(H,27,31)
comment: PA21A092 is a preclinical candidate for the pyrazoleamides, a novel class of antimalarial compounds <Reference id=37897/>. The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
iupac name: N-[4-(4-chloro-2-fluorophenyl)-2,5-dimethylpyrazol-3-yl]-2-(2-propan-2-ylbenzimidazol-1-yl)acetamide
synonym: PA92
approved: f
ligand name: PA21A092
type: SyntheticOrganicLigand

bulaquine
isomeric SMILES: COc1cc(NC(CCCN/C(=C/2/CCOC2=O)/C)C)c2c(c1)cccn2
in ch i key: ADCOUXIGWFEYJP-OBGWFSINSA-N
in ch i: InChI=1S/C21H27N3O3/c1-14(6-4-9-22-15(2)18-8-11-27-21(18)25)24-19-13-17(26-3)12-16-7-5-10-23-20(16)19/h5,7,10,12-14,22,24H,4,6,8-9,11H2,1-3H3/b18-15+
comment: Bulaquine is an 8-aminoquinoline derivative that has antimalarial activity and is a synthetic analogue of <Ligand id=9952/>. The INN record for bulaquine indicates that it is a racemic mixture. The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
iupac name: (3E)-3-[1-[4-[(6-methoxyquinolin-8-yl)amino]pentylamino]ethylidene]oxolan-2-one
xref: CHEMBL2106578
synonym: CDRI-80/53
synonym: elubaquine
approved: f
ligand name: bulaquine
type: SyntheticOrganicLigand

AZ8838
canonical SMILES: CCCc1cc(F)ccc1C(c1ncc[nH]1)O
isomeric SMILES: CCCc1cc(F)ccc1[C@@H](c1ncc[nH]1)O
in ch i key: IDFPQEHZYBXIFO-LBPRGKRZSA-N
in ch i: InChI=1S/C13H15FN2O/c1-2-3-9-8-10(14)4-5-11(9)12(17)13-15-6-7-16-13/h4-8,12,17H,2-3H2,1H3,(H,15,16)/t12-/m0/s1
comment: AZ8838 is a PAR2 antagonist that binds to PAR2 in a fully occluded pocket near the extracellular surface and competes with the tethered ligand. It was optimised from the weak antagonist, <Ligand id=9586/> <Reference id=33052/>.
iupac name: (S)-(4-fluoro-2-propylphenyl)(1H-imidazol-2-yl)methanol
approved: f
ligand name: AZ8838
type: SyntheticOrganicLigand

RIPK2 inhibitor 3
in ch i key: MJLYDVMFNHZMLV-UHFFFAOYSA-N
comment: This is an orally active RIPK2 inhibitor phosphate ester prodrug <Reference id=37924/><Reference id=37925/>. It is rapidly cleaved by alkaline phosphatases on contact with intestinal tissue and in whole blood. The prodrug formulation was designed to limit systemic exposure, and to focus activity at the preferred site of action in gut tissue. A crystal structure of RIPK2 in complex with inhibitor 3 has been submitted to the PDB with ID 6RN8.
iupac name: 2-[4-(1,3-benzothiazol-5-ylamino)-6-tert-butylsulfonylquinazolin-7-yl]oxyethyl dihydrogen phosphate
synonym: compound 3 [PMID: 31265286]
synonym: Example 1 [WO2014043446A1]
synonym: GSK2983559
approved: f
ligand name: RIPK2 inhibitor 3
type: SyntheticOrganicLigand

arteflene
isomeric SMILES: O=C1C[C@H]2C[C@@H]([C@@H]1C)OO[C@@]2(C)/C=C/c1ccc(cc1C(F)(F)F)C(F)(F)F
in ch i key: LRTRTVPZZJAADL-DAHZFVMQSA-N
in ch i: InChI=1S/C19H18F6O3/c1-10-15(26)8-13-9-16(10)27-28-17(13,2)6-5-11-3-4-12(18(20,21)22)7-14(11)19(23,24)25/h3-7,10,13,16H,8-9H2,1-2H3/b6-5-/t10-,13+,16+,17+/m1/s1
comment: Arteflene is a synthetic endoperoxide with antimalarial activity. It is derived from yingzhaosu A, a phytochemical endoperoxide isolated from A. uncinatus and structurally unrelated to the artemisinins <Reference id=41730/>. The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
iupac name: (1R,4S,5S,8R)-8-[(Z)-2-[2,4-bis(trifluoromethyl)phenyl]ethenyl]-4,8-dimethyl-6,7-dioxabicyclo[3.3.1]nonan-3-one
xref: CHEMBL380230
synonym: Ro 42-1611
approved: f
ligand name: arteflene
type: SyntheticOrganicLigand

KZR-616
in ch i key: GHYOCDFICYLMRF-UTIIJYGPSA-N
in ch i: InChI=1S/C30H42N4O8/c1-19(31-24(35)17-34-12-14-41-15-13-34)28(38)33-25(26(36)21-8-10-22(40-3)11-9-21)29(39)32-23(16-20-6-4-5-7-20)27(37)30(2)18-42-30/h6,8-11,19,23,25-26,36H,4-5,7,12-18H2,1-3H3,(H,31,35)(H,32,39)(H,33,38)/t19-,23-,25-,26+,30+/m0/s1
comment: KZR-616 is a first-in-class, selective and irreversible immunoproteasome inhibitor that results in anti-inflammatory activity in vitro and models of inflammatory conditions. It is a tripeptide epoxyketone-based molecule. At the molecular level KZR-616 inhibits the proteolytic activities of the low molecular mass polypeptide-7 (LMP7, a.k.a. proteasome subunit β8) and low molecular mass polypeptide-2 (LMP2, a.k.a. proteasome subunit β9) subunits of the 20S immunoproteasome complex <Reference id=37888/><Reference id=42693/>. Inhibition of a secondary immunoproteasome subunit, in this case LMP2 is required to achieve a multicytokine inhibitory effect.
synonym: compound 12 [PMID: 30380863]
synonym: KZR616
approved: f
ligand name: KZR-616
type: SyntheticOrganicLigand

bremelanotide
in ch i key: FFHBJDQSGDNCIV-MFVUMRCOSA-N
in ch i: InChI=1S/C50H68N14O10/c1-3-4-16-35(58-29(2)65)43(67)64-41-25-42(66)54-20-11-10-18-37(49(73)74)60-46(70)39(23-31-26-56-34-17-9-8-15-33(31)34)62-44(68)36(19-12-21-55-50(51)52)59-45(69)38(22-30-13-6-5-7-14-30)61-47(71)40(63-48(41)72)24-32-27-53-28-57-32/h5-9,13-15,17,26-28,35-41,56H,3-4,10-12,16,18-25H2,1-2H3,(H,53,57)(H,54,66)(H,58,65)(H,59,69)(H,60,70)(H,61,71)(H,62,68)(H,63,72)(H,64,67)(H,73,74)(H4,51,52,55)/t35-,36-,37-,38+,39-,40-,41-/m0/s1
comment: Bremelanotide is a stabilised, cyclic derivative of αMSH. Although it exhibits little selectivity across the melanocortin receptor family (with the exception of MC2, the ACTH receptor), bremelanotide's ability to increase female sexual arousal/desire is attributed primarily to agonist activity at the MC3 and MC4 receptors <Reference id=37857/>.
iupac name: (3S,6S,9R,12S,15S,23S)-15-[[(2S)-2-acetamidohexanoyl]amino]-9-benzyl-6-[3-(diaminomethylideneamino)propyl]-12-(1H-imidazol-5-ylmethyl)-3-(1H-indol-3-ylmethyl)-2,5,8,11,14,17-hexaoxo-1,4,7,10,13,18-hexazacyclotricosane-23-carboxylic acid
xref: CHEMBL2070241
synonym: PT-141
synonym: PT141
synonym: Vyleesi®
approved: t
ligand name: bremelanotide
type: PeptideLigand

albitiazolium
canonical SMILES: OCCc1sc[n+](c1C)CCCCCCCCCCCC[n+]1csc(c1C)CCO
isomeric SMILES: OCCc1sc[n+](c1C)CCCCCCCCCCCC[n+]1csc(c1C)CCO
in ch i key: UZPXHZIQHWKNPF-UHFFFAOYSA-N
in ch i: InChI=1S/C24H42N2O2S2/c1-21-23(13-17-27)29-19-25(21)15-11-9-7-5-3-4-6-8-10-12-16-26-20-30-24(14-18-28)22(26)2/h19-20,27-28H,3-18H2,1-2H3/q+2
comment: Albitiazolium was the clinical lead from the bisthiazolium series, a novel class of choline analogue with potent antimalarial activity <Reference id=37858/><Reference id=37856/>. We display the structure of the parent compound, with PubChem and ChEMBL links provided in the table below. However, the INN-assigned compound is in complex with bromide (represented in PubChem CID 11377022) and this compound is used in the experimental data listed under the 'biological activity' tab. The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
iupac name: 2-[3-[12-[5-(2-hydroxyethyl)-4-methyl-1,3-thiazol-3-ium-3-yl]dodecyl]-4-methyl-1,3-thiazol-3-ium-5-yl]ethanol
xref: CHEMBL1183040
synonym: SAR97276
synonym: T3
synonym: SAR97276A
approved: f
ligand name: albitiazolium
type: SyntheticOrganicLigand

OD36
canonical SMILES: Clc1cc2OCCOCCNc3nc4c(c(c1)c2)cnn4cc3
isomeric SMILES: Clc1cc2OCCOCCNc3nc4c(c(c1)c2)cnn4cc3
in ch i key: KTSDBMVHAKWDRK-UHFFFAOYSA-N
in ch i: InChI=1S/C16H15ClN4O2/c17-12-7-11-8-13(9-12)23-6-5-22-4-2-18-15-1-3-21-16(20-15)14(11)10-19-21/h1,3,7-10H,2,4-6H2,(H,18,20)
comment: OD36-induced inhibition of RIPK2 produces anti-inflammatory activity in animal models of inflammatory bowel conditions <Reference id=37848/>.
iupac name: 4-chloro-7,10-dioxa-13,17,18,21-tetrazatetracyclo[12.5.2.12,6.017,20]docosa-1(20),2(22),3,5,14(21),15,18-heptaene
approved: f
ligand name: OD36
type: SyntheticOrganicLigand

BAY-8002
in ch i key: CLAUJSRBKSRTGQ-UHFFFAOYSA-N
in ch i: InChI=1S/C20H14ClNO5S/c21-17-11-10-14(28(26,27)13-6-2-1-3-7-13)12-16(17)19(23)22-18-9-5-4-8-15(18)20(24)25/h1-12H,(H,22,23)(H,24,25)
comment: BAY-8002 inhibits lactate transport via the monocarboxylate transporter 1 (MCT1: SLC16A1) <Reference id=37847/>. [3H]-BAY-8002 binds to MCT1 with a Kd of 7.9 nM.
iupac name: 2-[[5-(benzenesulfonyl)-2-chlorobenzoyl]amino]benzoic acid
synonym: BAY8002
synonym: BAY 8002
approved: f
ligand name: BAY-8002
type: SyntheticOrganicLigand

zilucoplan
in ch i key: JDXCOXKBIGBZSK-PSNKNOTQSA-N
comment: Zilucoplan (RA101495) is a synthetic, macrocyclic peptide that blocks the cleavage of complement C5 into C5a and C5b which occurs as a consequence of activation of the classical, alternative, or lectin pathways. This mechanism of action inhibits formation of the membrane attack complex (MAC). It was developed by RaPharma for the treatment of tissue-based complement-mediated disorders.
synonym: RA101495
approved: f
ligand name: zilucoplan
type: PeptideLigand

compound 21b [PMID: 31136173]
canonical SMILES: COc1cc(ccc1OC)c1cnc2c(c1)c(C#Cc1cccnc1)c[nH]2
isomeric SMILES: COc1cc(ccc1OC)c1cnc2c(c1)c(C#Cc1cccnc1)c[nH]2
in ch i key: CJTVDIBZBUWIFC-UHFFFAOYSA-N
in ch i: InChI=1S/C22H17N3O2/c1-26-20-8-7-16(11-21(20)27-2)18-10-19-17(13-24-22(19)25-14-18)6-5-15-4-3-9-23-12-15/h3-4,7-14H,1-2H3,(H,24,25)
comment: Compound 21b is reported as a non-selective inhibitor of AP2 associated kinase 1 (AAK1) <Reference id=37814/>, a kinase that is involved in protein trafficking in endocytic membranes via regulation of subunits within the AP2 adaptor complex. The host AP2 complex is expoited by viruses to enable host cell infection and viral assembly <Reference id=37817/>. Host AAK1 is required for the life cycles of Flaviviridae family viruses, including the Dengue and Ebola viruses <Reference id=37815/><Reference id=37816/><Reference id=37817/>, making AAK1 a potential drug target for the development of broad-spectrun anti-viral agents <Reference id=37816/>.
iupac name: 3-{2-[5-(3,4-dimethoxyphenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]ethynyl}pyridine
approved: f
ligand name: compound 21b [PMID: 31136173]
type: SyntheticOrganicLigand

ZAK inhibitor 6p
in ch i key: QRDCOOSKIFYKIQ-UHFFFAOYSA-N
comment: This compound is reported as a potent, selective and orally active inhibitor of sterile alpha motif and leucine zipper containing kinase (ZAK) <Reference id=37813/>. It exhibits predicted antihypertrophic cardiomyopathy (HCM) efficacy in vivo in a spontaneous hypertensive rat (SHR) model.
iupac name: N-(2,4-Difluoro-3-(4-(3-methoxy-1H-pyrazolo[3,4-b]pyridin-5-yl)-1H-1,2,3-triazol-1-yl)phenyl)-[1,1'-biphenyl]-3-sulfonamide
approved: f
ligand name: ZAK inhibitor 6p
type: SyntheticOrganicLigand

RIPK3 inhibitor 42
in ch i key: RIVQMLWSKYAVFY-UHFFFAOYSA-N
comment: Compound 42 is reported as a selective inhibitor of receptor-interacting protein kinase 3 (RIPK3), that exhibits potent antinecroptotic activity in vitro, and significant anti-inflammatory action in vivo <Reference id=37812/>. Structurally it is a derivative of <Ligand id=10387/>.
iupac name: N-(6-(3-(3-(3-Bromophenyl)ureido)-4-fluorophenoxy)benzo[d]thiazol-2-yl)cyclopropanecarboxamide
approved: f
ligand name: RIPK3 inhibitor 42
type: SyntheticOrganicLigand

PDE4 inhibitor 16
in ch i key: OIDQRHGTWLIKKZ-NRFANRHFSA-N
in ch i: InChI=1S/C23H26N2O3/c1-15-4-6-18-17(13-24-20(18)10-15)5-7-21-19-12-23(28-3)22(27-2)11-16(19)8-9-25(21)14-26/h4,6,10-14,21,24H,5,7-9H2,1-3H3/t21-/m0/s1
comment: This compound has been reported as a selective inhibitor of phosphodiesterase 4 (PDE4) <Reference id=37811/>. Chemically this compound is a synthetic tetrahydro-isoquinoline analogue of the naturally occurring plant alkaloid berberine (PubChem CID 2353).
iupac name: (S)-6,7-Dimethoxy-1-(2-(6-methyl-1H-indol-3-yl)ethyl)-3,4-dihydroisoquinoline-2(1H)-carbaldehyde
approved: f
ligand name: PDE4 inhibitor 16
type: SyntheticOrganicLigand

CRAC channel inhibitor 5b [PMID: 26256403]
in ch i key: YPDVKFTYHRFBSZ-UHFFFAOYSA-N
in ch i: InChI=1S/C19H23ClN2O/c1-5-18(15-8-6-14(2)7-9-15)22(4)19(23)21(3)17-12-10-16(20)11-13-17/h6-13,18H,5H2,1-4H3
comment: CRAC channel inhibitor 5b is a selective ORAI1 inhibitor that was identified through SAR of <Ligand id=10041/> <Reference id=35944/>.
iupac name: 1-(4-chlorophenyl)-1,3-dimethyl-3-[1-(4-methylphenyl)propyl]urea
approved: f
ligand name: CRAC channel inhibitor 5b [PMID: 26256403]
type: SyntheticOrganicLigand

CDRI-97/78
in ch i key: LKAAAECAYCDCQW-UHFFFAOYSA-N
in ch i: InChI=1S/C28H36O8/c1-17(24-15-33-28(36-35-24)21-11-18-10-19(13-21)14-22(28)12-18)20-4-6-23(7-5-20)34-27(2,3)16-32-26(31)9-8-25(29)30/h4-7,18-19,21-22,24H,1,8-16H2,2-3H3,(H,29,30)
comment: CDRI-97/78 is a novel trioxane peroxide with promising antimalarial activity <Reference id=37836/>. It is a simplified analogue of <Ligand id=9954/> and retains the crucial endoperoxide bridge.
iupac name: 4-[2-methyl-2-[4-(1-spiro[1,2,4-trioxane-3,2'-adamantane]-6-ylethenyl)phenoxy]propoxy]-4-oxobutanoic acid
approved: f
ligand name: CDRI-97/78
type: SyntheticOrganicLigand

naphazoline
canonical SMILES: C1CN=C(N1)Cc1cccc2c1cccc2
isomeric SMILES: C1CN=C(N1)Cc1cccc2c1cccc2
in ch i key: CNIIGCLFLJGOGP-UHFFFAOYSA-N
in ch i: InChI=1S/C14H14N2/c1-2-7-13-11(4-1)5-3-6-12(13)10-14-15-8-9-16-14/h1-7H,8-10H2,(H,15,16)
comment: Marketed formulations may contain naphazoline hydrochloride (PubChem CID 11079) or naphazoline nitrate (PubChem CID 16218420).
iupac name: 2-(naphthalen-1-ylmethyl)-4,5-dihydro-1H-imidazole
xref: CHEMBL761
synonym: Nafazair
synonym: Albalon
synonym: Naphcon®
approved: t
ligand name: naphazoline
type: SyntheticOrganicLigand

naphthoquine
in ch i key: VEVMYTDOWUQLGI-UHFFFAOYSA-N
in ch i: InChI=1S/C24H28ClN3O/c1-24(2,3)27-14-15-12-22(17-6-4-5-7-18(17)23(15)29)28-20-10-11-26-21-13-16(25)8-9-19(20)21/h8-13,27,29H,4-7,14H2,1-3H3,(H,26,28)
comment: Naphthoquine is a 4-aminoquinoline antimalarial compound. The marketed formulations contain naphthoquine phosphate (PubChem CID 9851774). The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
iupac name: 2-[(tert-butylamino)methyl]-4-[(7-chloroquinolin-4-yl)amino]-5,6,7,8-tetrahydronaphthalen-1-ol
approved: f
ligand name: naphthoquine
type: SyntheticOrganicLigand

JPC-3210
in ch i key: DYULPLHABFGTOQ-UHFFFAOYSA-N
in ch i: InChI=1S/C21H26F4N2O/c1-19(2,3)14-7-13(11-27-20(4,5)6)17(28)15(9-14)12-8-16(22)18(26-10-12)21(23,24)25/h7-10,27-28H,11H2,1-6H3
comment: JPC-3210 has been identified as the lead for the 2-aminomethylphenol class of compounds and demonstrates promising antimalarial activity <Reference id=37842/>. The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
iupac name: 4-tert-butyl-2-[(tert-butylamino)methyl]-6-[5-fluoro-6-(trifluoromethyl)pyridin-3-yl]phenol
synonym: MMV646
synonym: MMV892646
approved: f
ligand name: JPC-3210
type: SyntheticOrganicLigand

compound 3l [PMID: 30637955]
in ch i key: KQGVKXJLEHXBDS-CBHGIOBQSA-N
in ch i: InChI=1S/C36H38F3N3O3/c1-24-17-29(21-30(18-24)35(45)42(3)25(2)28-14-8-5-9-15-28)34(44)41-32(20-26-11-6-4-7-12-26)33(43)23-40-22-27-13-10-16-31(19-27)36(37,38)39/h4-19,21,25,32-33,40,43H,20,22-23H2,1-3H3,(H,41,44)/t25-,32+,33-/m1/s1
comment: Compound 3l is a potent and selective nonpeptide β-secretase 2 (BACE2) inhibitor <Reference id=37807/>. It is one of the compounds claimed in patent US9512099 for use in the treatment of Alzheimer's disease or type 2 diabetes <Reference id=37808/>.
approved: f
ligand name: compound 3l [PMID: 30637955]
type: SyntheticOrganicLigand

NPC1161B
in ch i key: UEFVAUCKVCFRDW-CQSZACIVSA-N
comment: NPC1161B is a next-generation lead compound for the 8-aminoquinoline class of antimalarial compounds. It is the (-)-enantiomer of NPC1161C <Reference id=37845/>. The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
iupac name: (4R)-N-[5-(3,4-dichlorophenoxy)-6-methoxy-4-methylquinolin-8-yl]pentane-1,4-diamine
xref: CHEMBL1739268
synonym: NPC-1161B
approved: f
ligand name: NPC1161B
type: SyntheticOrganicLigand

tebuquine
in ch i key: BCHMRNALCJISMZ-UHFFFAOYSA-N
in ch i: InChI=1S/C26H25Cl2N3O/c1-26(2,3)30-15-17-12-20(14-22(25(17)32)16-4-6-18(27)7-5-16)31-23-10-11-29-24-13-19(28)8-9-21(23)24/h4-14,30,32H,15H2,1-3H3,(H,29,31)
comment: Tebuquine is a 4-aminoquinoline antimalarial compound.
iupac name: 2-[(tert-butylamino)methyl]-6-(4-chlorophenyl)-4-[(7-chloroquinolin-4-yl)amino]phenol
xref: CHEMBL339049
synonym: WR 228,258
approved: f
ligand name: tebuquine
type: SyntheticOrganicLigand

AQ-13
canonical SMILES: CCN(CCCNc1ccnc2c1ccc(c2)Cl)CC
isomeric SMILES: CCN(CCCNc1ccnc2c1ccc(c2)Cl)CC
in ch i key: NCPLTAGJJVCHOW-UHFFFAOYSA-N
in ch i: InChI=1S/C16H22ClN3/c1-3-20(4-2)11-5-9-18-15-8-10-19-16-12-13(17)6-7-14(15)16/h6-8,10,12H,3-5,9,11H2,1-2H3,(H,18,19)
comment: AQ-13 is a 4-aminoquinoline antimalarial compound related to <Ligand id=5535/> <Reference id=38169/><Reference id=38184/>. The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
iupac name: N'-(7-chloroquinolin-4-yl)-N,N-diethylpropane-1,3-diamine
xref: CHEMBL144037
synonym: Ro 47-0543
approved: f
ligand name: AQ-13
type: SyntheticOrganicLigand

JMS-17-2
in ch i key: WOSMCMULWWHMIV-UHFFFAOYSA-N
in ch i: InChI=1S/C25H26ClN3O/c26-21-10-8-19(9-11-21)20-12-17-27(18-13-20)14-4-16-29-23-6-2-1-5-22(23)28-15-3-7-24(28)25(29)30/h1-3,5-11,15,20H,4,12-14,16-18H2
comment: JMS-17-2 is CX3CR1 (fractalkine receptor) antagonist that was developed as a tool compound to evaluate the oncological potential of antagonising the CX3CR1 pathway <Reference id=37794/>. Experimental evidence indicates that CX3CR1 has prometastatic activity in tumour cells, particulary in breast cancer cells. JMS-17-2 was developed to antagonise this action, to reduce metastatic seeding of circulating cancer cells to secondary tissues and reduce progression of established metastases. The compound is active, as the hydrochloride, in vitro and in vivo. It is one of the structures claimed in patent WO2012078633 <Reference id=37795/>.
iupac name: 5-[3-[4-(4-Chlorophenyl)-1-piperidinyl]propyl]pyrrolo[1,2-a]quinoxalin-4(5H)-one
synonym: JMS 17-2
approved: f
ligand name: JMS-17-2
type: SyntheticOrganicLigand

RIPK3 inhibitor 18
in ch i key: PETCZXAONWLUFT-UHFFFAOYSA-N
in ch i: InChI=1S/C29H25FN4O4/c1-17-18(2)25(38-22-13-14-31-26(16-22)33-27(35)19-5-6-19)12-11-24(17)32-28(36)23-4-3-15-34(29(23)37)21-9-7-20(30)8-10-21/h3-4,7-16,19H,5-6H2,1-2H3,(H,32,36)(H,31,33,35)
comment: Compound 18 is a type II DFG-out RIPK3 inhibitor <Reference id=37791/>. It was identified by a team in Bristol-Myers Squibb Research & Development laboratories.
iupac name: N-{4-[(2-cyclopropaneamidopyridin-4-yl)oxy]-2,3-dimethylphenyl}-1-(4-fluorophenyl)-2-oxo-1,2-dihydropyridine-3-carboxamide
approved: f
ligand name: RIPK3 inhibitor 18
type: SyntheticOrganicLigand

SZM594
in ch i key: SDSQERWTMKMZLA-UHFFFAOYSA-N
comment: SZM594 is a dual RIPK1/RIPK3 inhibitor that blocks necroptosis <Reference id=37789/>.
approved: f
ligand name: SZM594
type: SyntheticOrganicLigand

TAK-632
in ch i key: OJFKUJDRGJSAQB-UHFFFAOYSA-N
comment: TAK-632 is a pan-RAF kinase inhibitor <Reference id=37788/>. It binds human BRAF in the DFG-out conformation. TAK-632 inhibits RIPK1/3-induced necrosome formation and necroptosis, and this action was shown to be mediated by direct ligand interaction with RIPK1 and RIPK3 (and inhibition of their kinase activities) <Reference id=37789/><Reference id=37812/>.
xref: CHEMBL3125890
synonym: TAK632
synonym: compound 8B [PMID: 23906342]
approved: f
ligand name: TAK-632
type: SyntheticOrganicLigand

celastrol
in ch i key: KQJSQWZMSAGSHN-JJWQIEBTSA-N
in ch i: InChI=1S/C29H38O4/c1-17-18-7-8-21-27(4,19(18)15-20(30)23(17)31)12-14-29(6)22-16-26(3,24(32)33)10-9-25(22,2)11-13-28(21,29)5/h7-8,15,22,31H,9-14,16H2,1-6H3,(H,32,33)/t22-,25-,26-,27+,28-,29+/m1/s1
comment: Celastrol is a plant-derived (from Tripterygium wilfordi, the Thunder god vine) natural product that has antioxidant, anti-inflammatory <Reference id=37780/><Reference id=38029/> and anti-obesity effects <Reference id=37779/>. It has been reported as an inhibitor of RGS17 <Reference id=42197/>.
iupac name: (2R,4aS,6aR,6aS,14aS,14bR)-10-hydroxy-2,4a,6a,6a,9,14a-hexamethyl-11-oxo-1,3,4,5,6,13,14,14b-octahydropicene-2-carboxylic acid
synonym: compound 2 [PMID: 28621943]
approved: f
ligand name: celastrol
type: NaturalProductLigand

NUDT7-COV-1
in ch i key: ZJGDVCKAHPNDQT-UHFFFAOYSA-N
comment: NUDT7-COV-1 is a covalent inhibitor of the pyrophosphatase NUDT7 <Reference id=37767/>. It was discovered using a combination of electrophile fragment screening and high-throughput crystallography. We show the structure without specified stereochemistry to represent the racemic mixture, but the co-crystal structure reveals that the S-enantiomer is the active species.
iupac name: 2-{3-[1-(2-chloroacetyl)pyrrolidin-2-yl]phenyl}-N-(3-chlorophenyl)acetamide
approved: f
ligand name: NUDT7-COV-1
type: SyntheticOrganicLigand

ARS-1620
in ch i key: ZRPZPNYZFSJUPA-UHFFFAOYSA-N
comment: ARS-1620 was designed to target mutated KRASG12C in cancer <Reference id=37762/>. It binds covalently to GDP-bound KRASG12C and traps it in the inactive conformation. Structurally ARS-1620 is the S-atropisomer. It represents a pharmacological tool that is suitable for use in in vitro and in vivo experiments to further explore KRAS dependency in KRAS mutant cancers. The chemical structure is claimed in Araxes Pharma's patent US9840516B2
iupac name: 1-[4-[6-chloro-8-fluoro-7-(2-fluoro-6-hydroxyphenyl)quinazolin-4-yl]piperazin-1-yl]prop-2-en-1-one
synonym: ARS1620
synonym: example 227 [US9840516B2]
approved: f
ligand name: ARS-1620
type: SyntheticOrganicLigand

MK-7145
in ch i key: OCKGFTQIICXDQW-ZEQRLZLVSA-N
in ch i: InChI=1S/C26H30N2O6/c1-15-17(3-5-19-21(15)13-33-25(19)31)23(29)11-27-7-9-28(10-8-27)12-24(30)18-4-6-20-22(16(18)2)14-34-26(20)32/h3-6,23-24,29-30H,7-14H2,1-2H3/t23-,24-/m0/s1
comment: MK-7145 is a Kir1.1 (ROMK) inhibitor that was designed as a novel diuretic <Reference id=37759/>. The chemical structure is claimed as example 2A in patent WO2010129379 <Reference id=37760/>.
iupac name: 5-[(1R)-1-hydroxy-2-[4-[(2R)-2-hydroxy-2-(4-methyl-1-oxo-3H-2-benzofuran-5-yl)ethyl]piperazin-1-yl]ethyl]-4-methyl-3H-2-benzofuran-1-one
xref: CHEMBL3696475
synonym: example 2A [WO2010129379]
synonym: MK7145
approved: f
ligand name: MK-7145
type: SyntheticOrganicLigand

NY0116
canonical SMILES: NC(=N)NCCOC(c1ccccc1)(c1ccccc1)c1ccccc1
isomeric SMILES: NC(=N)NCCOC(c1ccccc1)(c1ccccc1)c1ccccc1
in ch i key: FZXFGYLHTRBHNJ-UHFFFAOYSA-N
in ch i: InChI=1S/C22H23N3O/c23-21(24)25-16-17-26-22(18-10-4-1-5-11-18,19-12-6-2-7-13-19)20-14-8-3-9-15-20/h1-15H,16-17H2,(H4,23,24,25)
comment: NY0116 is a small-molecule neuromedin U receptor agonist with selectivity for the NMU2 receptor (NMUR2) <Reference id=37734/>.
iupac name: 2-(2-trityloxyethyl)guanidine
approved: f
ligand name: NY0116
type: SyntheticOrganicLigand

CPN-267
in ch i key: HIFICJJBGBSZMZ-YWIJTBFMSA-N
in ch i: InChI=1S/C50H66N16O8S/c1-50(25-29-27-60-34-14-5-3-12-32(29)34,65-44(71)38(61-41(68)23-30-10-9-21-75-30)22-28-26-59-33-13-4-2-11-31(28)33)47(74)64-36(16-7-19-58-49(55)56)46(73)66-20-8-17-39(66)45(72)62-35(15-6-18-57-48(53)54)43(70)63-37(42(52)69)24-40(51)67/h2-5,9-14,21,26-27,35-39,59-60H,6-8,15-20,22-25H2,1H3,(H2,51,67)(H2,52,69)(H,61,68)(H,62,72)(H,63,70)(H,64,74)(H,65,71)(H4,53,54,57)(H4,55,56,58)/t35-,36-,37-,38-,39-,50-/m0/s1
comment: CPN-267 is a Neuromedin U receptor 1 (NMUR1) selective agonist <Reference id=37733/>. It is a hexapeptide based on the C-terminal core peptide of human neuromedin U. α-methylation of the Trp residue at position 3 improves the peptide's agonistic activity and its selectivity for NMUR1.
iupac name: deamino-2-thien-2-yl-glycyl-L-tryptophyl-alpha-methyl-L-tryptophyl-L-arginyl-L-prolyl-L-arginyl-L-asparaginamide
synonym: C-terminal core peptide derivative of neuromedin U, bearing (α-Me)Trp2
synonym: analogue 7b [PMID: 28548497]
synonym: NMUR1 agonist C7b
approved: f
ligand name: CPN-267
type: PeptideLigand

pexacerfont
canonical SMILES: CCC(Nc1nc(C)nc2n1nc(c2c1ccc(nc1C)OC)C)C
in ch i key: LBWQSAZEYIZZCE-SNVBAGLBSA-N
in ch i: InChI=1S/C18H24N6O/c1-7-10(2)19-18-22-13(5)21-17-16(12(4)23-24(17)18)14-8-9-15(25-6)20-11(14)3/h8-10H,7H2,1-6H3,(H,19,21,22)/t10-/m1/s1
comment: Pexacerfont (BMS-562086) is an orally active corticotropin releasing factor-1 (CRF-1) receptor antagonist <Reference id=37731/>.
xref: CHEMBL482950
synonym: BMS-562086
synonym: BMS562086
approved: f
ligand name: pexacerfont
type: SyntheticOrganicLigand

verucerfont
in ch i key: VKHVAUKFLBBZFJ-SFHVURJKSA-N
in ch i: InChI=1S/C22H26N6O2/c1-7-18(22-24-15(5)27-30-22)25-19-11-13(3)23-21-20(14(4)26-28(19)21)17-9-8-16(29-6)10-12(17)2/h8-11,18,25H,7H2,1-6H3/t18-/m0/s1
comment: Verucerfont (NBI-77860 or GSK561679) is an orally available, brain penetrant and selective corticotropin releasing factor-1 (CRF-1) receptor antagonist <Reference id=37728/>.
iupac name: 3-(4-methoxy-2-methylphenyl)-2,5-dimethyl-N-[(1S)-1-(3-methyl-1,2,4-oxadiazol-5-yl)propyl]pyrazolo[1,5-a]pyrimidin-7-amine
synonym: GSK561679
synonym: GSK-561679
synonym: NBI-77860
synonym: NBI77860
synonym: Compound (S)-8d [PMID: 21074436]
approved: f
ligand name: verucerfont
type: SyntheticOrganicLigand

CP-316,311
canonical SMILES: CCC(Oc1cc(C)nc(c1C)Oc1c(C)cc(cc1C)C)CC
isomeric SMILES: CCC(Oc1cc(C)nc(c1C)Oc1c(C)cc(cc1C)C)CC
in ch i key: ZSEJGVQTBLJRCQ-UHFFFAOYSA-N
in ch i: InChI=1S/C21H29NO2/c1-8-18(9-2)23-19-12-16(6)22-21(17(19)7)24-20-14(4)10-13(3)11-15(20)5/h10-12,18H,8-9H2,1-7H3
comment: CP-316,311 is an orally active, small molecule corticotropin releasing factor-1 (CRF-1) receptor antagonist <Reference id=37727/>.
iupac name: 3,6-dimethyl-4-pentan-3-yloxy-2-(2,4,6-trimethylphenoxy)pyridine
xref: CHEMBL270738
synonym: CP-316311
synonym: CP316311
synonym: compound 2 [PMID: 18260619]
approved: f
ligand name: CP-316,311
type: SyntheticOrganicLigand

ONO-2333MS
in ch i key: LDIOUQIXNSSOGU-UHFFFAOYSA-N
in ch i: InChI=1S/C22H27ClN4O/c1-5-14(6-2)24-21-17-8-7-9-19(17)25-22-20(13(3)26-27(21)22)16-11-10-15(28-4)12-18(16)23/h10-12,14,24H,5-9H2,1-4H3
comment: ONO-2333MS is an orally active corticotropin releasing factor-1 (CRF-1) receptor antagonist <Reference id=37726/>.
xref: CHEMBL1819077
synonym: ONO-2333
synonym: ONO2333
synonym: ONO2333MS
synonym: compound 7b [PMID: 21865047]
approved: f
ligand name: ONO-2333MS
type: SyntheticOrganicLigand

NBI-34041
in ch i key: AKLMUGFDGONMAA-UHFFFAOYSA-N
in ch i: InChI=1S/C22H26Cl2N4/c1-4-6-16(7-5-2)27-10-11-28-22-19(27)12-14(3)25-21(22)20(26-28)17-9-8-15(23)13-18(17)24/h8-9,12-13,16H,4-7,10-11H2,1-3H3
comment: NBI-34041 is a corticotropin releasing factor-1 (CRF-1) receptor antagonist <Reference id=37724/>.
xref: CHEMBL188907
synonym: SB723620
synonym: SB-723620
synonym: NBI34041
synonym: compound 16a [PMID: 16078829]
approved: f
ligand name: NBI-34041
type: SyntheticOrganicLigand

I-C11
in ch i key: RSPKMGDZBNPGGF-UHFFFAOYSA-N
in ch i: InChI=1S/C31H24N4O5/c36-26-17-27-23(16-22(26)31(38)39)29(30(40-27)20-9-2-1-3-10-20)25-18-35(34-33-25)15-7-14-28(37)32-24-13-6-11-19-8-4-5-12-21(19)24/h1-6,8-13,16-18,36H,7,14-15H2,(H,32,37)(H,38,39)
comment: I-C11 is an inhibitor of the PTPN22 tyrosine phosphatase <Reference id=29957/><Reference id=37722/>. It binds both the active (orthosteric) site and an allosteric, PTPN22 unique site (S35TKYKADK42) that confers selectivity. The chemical structure for I-C11 is claimed in patent WO2009049098A2 <Reference id=37723/>.
iupac name: 6-hydroxy-3-[1-[4-(naphthalen-1-ylamino)-4-oxobutyl]triazol-4-yl]-2-phenyl-1-benzofuran-5-carboxylic acid
xref: CHEMBL260920
approved: f
ligand name: I-C11
type: SyntheticOrganicLigand

NC1
isomeric SMILES: CCOC(=O)c1ccc(cc1)N=C1S/C(=C/c2ccc(c(c2)OC)OCc2ccc(cc2)C(=O)O)/C(=O)N1C
in ch i key: MEYCXOYFLJPZOT-FXALAWDZSA-N
in ch i: InChI=1S/C29H26N2O7S/c1-4-37-28(35)21-10-12-22(13-11-21)30-29-31(2)26(32)25(39-29)16-19-7-14-23(24(15-19)36-3)38-17-18-5-8-20(9-6-18)27(33)34/h5-16H,4,17H2,1-3H3,(H,33,34)/b25-16-,30-29?
comment: NC1 is reported as an allosteric inhibitor of tyrosine phosphatase PTPN22 <Reference id=37709/>. The binding mode of NC1 is noncompetitive. Its binding restricts the closure of the phosphatase's catalytic WPD-loop, and simultaneously binds to a second PTPN22-specific pocket which determines its selectivity for PTPN22 compared to other phosphatases.
iupac name: 4-[[4-[(Z)-[2-(4-ethoxycarbonylphenyl)imino-3-methyl-4-oxo-1,3-thiazolidin-5-ylidene]methyl]-2-methoxyphenoxy]methyl]benzoic acid
approved: f
ligand name: NC1
type: SyntheticOrganicLigand

compound 14 [PMID: 30925062]
in ch i key: QAWHHEOBNCCSJP-UHFFFAOYSA-N
in ch i: InChI=1S/C28H30N6OS/c1-18-9-10-21-22(16-18)36-28-23(21)27(31-26(32-28)20-8-5-11-30-17-20)34-14-12-33(13-15-34)24(25(29)35)19-6-3-2-4-7-19/h2-8,11,17-18,24H,9-10,12-16H2,1H3,(H2,29,35)
comment: Compound 14 is reported as a triple inhibitor of the multi-drug resistance-associated transporters ABCC1, ABCB1 and ABCG2 <Reference id=37703/>. This compound has a thienopyrimidine scaffold that has not previously been associated with ABCC1 inhibition.
iupac name: 2-[4-(7-methyl-2-pyridin-3-yl-5,6,7,8-tetrahydro-[1]benzothiolo[3,2-e]pyrimidin-4-yl)piperazin-1-yl]-2-phenylacetamide
approved: f
ligand name: compound 14 [PMID: 30925062]
type: SyntheticOrganicLigand

compound 20 [PMID: 30998356]
in ch i key: IUWWRSQCDUQDEZ-CAQPCFEESA-N
comment: Compound 20 was rationally designed as a potent, selective and orally active TTK protein kinase inhibitor with single agent efficacy against triple negative breast cancer cells <Reference id=37702/>. The pyrrolopyrimidine core of 20 interacts with residues within TTK's ATP binding pocket, and it forms three hydrogen bonds to the hinge region. The ligand/TTK co-crystal structure has been submitted to the PDB and has ID 6N6O.
iupac name: 4-[[5-Chloro-4-(4-hydroxy-4-methyl-cyclohexoxy)-7H-pyrrolo[2,3-d]pyrimidin-2-yl]amino]-N,N-dimethyl-3-[(1R)-2,2,2-trifluoro-1-methyl-ethoxy]benzamide
approved: f
ligand name: compound 20 [PMID: 30998356]
type: SyntheticOrganicLigand

stanozolol
in ch i key: LKAJKIOFIWVMDJ-IYRCEVNGSA-N
in ch i: InChI=1S/C21H32N2O/c1-19-11-13-12-22-23-18(13)10-14(19)4-5-15-16(19)6-8-20(2)17(15)7-9-21(20,3)24/h12,14-17,24H,4-11H2,1-3H3,(H,22,23)/t14-,15+,16-,17-,19-,20-,21-/m0/s1
comment: Stanozolol is a synthetic, orally active steroid that has anabolic and androgenic properties <Reference id=37680/>. Chemically, it is a 17α-alkylated derivative of <Ligand id=2856/>. It has low binding affinity for the androgen receptor, but is a strong activator of androgen receptor-induced protein synthesis and erythropoietin production <Reference id=37679/>.
xref: CHEMBL2079587
synonym: WIN-14833
synonym: WIN14833
synonym: WIN 14833
synonym: Winstrol®
synonym: Stromba®
synonym: Tevabolin®
approved: t
ligand name: stanozolol
type: SyntheticOrganicLigand

avapritinib
in ch i key: DWYRIWUZIJHQKQ-SANMLTNESA-N
in ch i: InChI=1S/C26H27FN10/c1-26(28,20-3-5-22(27)6-4-20)21-13-29-25(30-14-21)36-9-7-35(8-10-36)24-23-11-18(16-37(23)33-17-31-24)19-12-32-34(2)15-19/h3-6,11-17H,7-10,28H2,1-2H3/t26-/m0/s1
comment: Avapritinib (BLU-285) was developed by Blueprint Medicines as an oral precision therapy to selectively and potently inhibit KIT and PDGFRA mutant kinases <Reference id=37673/>. It is a Type I kinase inhibitor that binds the active kinase conformation. Avapritinib binds to the 'switch pocket' of KIT, a domain that regulates the enzyme's catalytic conformation. Compounds that act in this way are often referred to as switch control inhibitors <Reference id=37677/>. Another such switch control inhibitor is <Ligand id=9175/>.
iupac name: (1S)-1-(4-fluorophenyl)-1-[2-[4-[6-(1-methylpyrazol-4-yl)pyrrolo[2,1-f][1,2,4]triazin-4-yl]piperazin-1-yl]pyrimidin-5-yl]ethanamine
synonym: Ayvakit®
synonym: BLU-285
synonym: BLU285
synonym: Ayvakyt®
approved: t
ligand name: avapritinib
type: SyntheticOrganicLigand

DS21360717
in ch i key: VFVLUXBYMUKJIJ-DLBZAZTESA-N
in ch i: InChI=1S/C21H23N7O/c1-12-5-4-6-13(9-12)25-20-18-15(11-24-28-21(18)29)14(10-22)19(27-20)26-17-8-3-2-7-16(17)23/h4-6,9,11,16-17H,2-3,7-8,23H2,1H3,(H,28,29)(H2,25,26,27)/t16-,17+/m0/s1
comment: DS21360717 is a potent inhibitor of FER tyrosine kinase <Reference id=37669/>. It was designed by Daiichi Sankyo to inhibit protumourigenic activity of FER as a novel anticancer therapy. It was discovered through high-throughput screening, scaffold hopping and SAR-based chemical modification.
iupac name: 7-{[(1R,2S)-2-aminocyclohexyl]amino}-5-[(3-methylphenyl)amino]-4-oxo-3H,4H-pyrido[3,4-d]pyridazine-8-carbonitrile
synonym: compound 21 [Taniguchi et al., 2019]
approved: f
ligand name: DS21360717
type: SyntheticOrganicLigand

FzM1.8
in ch i key: XGNNCRZDDAJBFU-UHFFFAOYSA-N
in ch i: InChI=1S/C18H14N2O4/c21-16-9-13(17(22)23)8-15(10-16)20-18(24)19-14-6-5-11-3-1-2-4-12(11)7-14/h1-10,21H,(H,22,23)(H2,19,20,24)
comment: FzM1.8 is a small-molecule allosteric agonist of FZD4 and activates the WNT/β-catenin pathway <Reference id=37406/>.
iupac name: 3-hydroxy-5-{[(naphthalen-2-yl)carbamoyl]amino}benzoic acid
approved: f
ligand name: FzM1.8
type: SyntheticOrganicLigand

XY101
in ch i key: AUIAOCHKUNGZHV-UHFFFAOYSA-N
in ch i: InChI=1S/C25H20F7NO4S/c1-2-38(36,37)19-10-3-15(4-11-19)13-22(34)33-18-8-5-16(6-9-18)20-12-7-17(14-21(20)26)23(35,24(27,28)29)25(30,31)32/h3-12,14,35H,2,13H2,1H3,(H,33,34)
comment: XY101 is a potent, selective, and orally active retinoic acid receptor-related orphan receptor γ (RORγ) inverse agonist <Reference id=37666/>. It was developed as a potential drug for the treatment of castration-resistant prostate cancer (CRPC). RORγ directly stimulates transcription of the androgen receptor (AR) gene, and hence increases AR expression. As proof of concept, RORγ inverse agonists have been shown to reduce expression and activity of ARs that are active in CRPC, and thereby to decrease tumour growth and metastasis <Reference id=37667/>.
synonym: compound 27 [PMID: 30964293]
synonym: XY-101
approved: f
ligand name: XY101
type: SyntheticOrganicLigand

compound 2q [PMID: 30986068]
in ch i key: FHKPLLOSJHHKNU-INIZCTEOSA-N
in ch i: InChI=1S/C22H29N7O3/c1-4-29-14(2)17(11-25-29)19-26-18-20(27(19)3)23-13-24-21(18)32-16-5-8-28(12-16)22(30)15-6-9-31-10-7-15/h11,13,15-16H,4-10,12H2,1-3H3/t16-/m0/s1
comment: Compound 2q is a PI3Kδ selective inhibitor <Reference id=37659/>. It is one of the chemical structures that is claimed in Merck and Shanghai Chempartners' patent US20150353552A1 <Reference id=37665/>.
iupac name: [(3S)-3-[8-(1-ethyl-5-methylpyrazol-4-yl)-9-methylpurin-6-yl]oxypyrrolidin-1-yl]-(oxan-4-yl)methanone
synonym: example 2-8 [US20150353552]
approved: f
ligand name: compound 2q [PMID: 30986068]
type: SyntheticOrganicLigand

NSC61610
in ch i key: WSXIJTIFOWCMIQ-UHFFFAOYSA-N
in ch i: InChI=1S/C34H24N6O2/c41-33(35-25-9-5-7-23(19-25)31-37-27-11-1-2-12-28(27)38-31)21-15-17-22(18-16-21)34(42)36-26-10-6-8-24(20-26)32-39-29-13-3-4-14-30(29)40-32/h1-20H,(H,35,41)(H,36,42)(H,37,38)(H,39,40)
comment: NSC61610 is a LANCL2 modulator that was discovered using high-throughput, structure-based virtual screening <Reference id=37651/>. It has a poor drug-like profile, passing only one of the six Lipinski-like filters. <Ligand id=10363/> was designed as an improved version of NSC61610 (it passes three of the Lipinski rules).
iupac name: 1-N,4-N-bis[3-(1H-benzimidazol-2-yl)phenyl]benzene-1,4-dicarboxamide
xref: CHEMBL1562963
approved: f
ligand name: NSC61610
type: SyntheticOrganicLigand

BT-11
in ch i key: MVHWZNBAQIGPOQ-UHFFFAOYSA-N
in ch i: InChI=1S/C30H24N8O2/c39-29(25-13-5-11-23(31-25)27-33-19-7-1-2-8-20(19)34-27)37-15-17-38(18-16-37)30(40)26-14-6-12-24(32-26)28-35-21-9-3-4-10-22(21)36-28/h1-14H,15-18H2,(H,33,34)(H,35,36)
comment: BT-11 is an orally active anti-inflammatory agent that operates as a LANCL2 pathway activator <Reference id=37649/>. It is being developed by Landos Biopharma, and is Example 1 as claimed in patent US9556146B2 <Reference id=37658/>. The physicochemical properties of BT-11 suggest that it may offer a drug with minimal systemic distribution, and be more suited to local action in the acidic environment of the gut.
iupac name: [4-[6-(1H-benzimidazol-2-yl)pyridine-2-carbonyl]piperazin-1-yl]-[6-(1H-benzimidazol-2-yl)pyridin-2-yl]methanone
synonym: analogue 7 [PMID: 27933891]
synonym: BT11
synonym: Example 1 [US9556146B2]
approved: f
ligand name: BT-11
type: SyntheticOrganicLigand

abscisic acid
canonical SMILES: OC(=O)C=C(C=CC1(O)C(=CC(=O)CC1(C)C)C)C
isomeric SMILES: OC(=O)/C=C(/C=C/C1(O)C(=CC(=O)CC1(C)C)C)/C
in ch i key: JLIDBLDQVAYHNE-LXGGSRJLSA-N
in ch i: InChI=1S/C15H20O4/c1-10(7-13(17)18)5-6-15(19)11(2)8-12(16)9-14(15,3)4/h5-8,19H,9H2,1-4H3,(H,17,18)/b6-5+,10-7-
comment: We show the compound without specified stereochemistry to represent racemic abscisic acid. The (1S)- or (+)-enantiomer (PubChem CID 12305886), is the naturally occurring and more active form of abscisic acid. Abscisic acid activates human granulocytes <Reference id=37643/> and stimulates insulin secretion by human and murine pancreatic β cells <Reference id=37644/>, via similar signalling pathways, that require a LANCL2-containing protein complex linked to a Gi protein, that ultimately leads to elevation of the intracellular Ca2+ concentration <Reference id=37642/>. In cellular and animal models abscisic acid exerts anti-inflammatory <Reference id=37647/><Reference id=37646/><Reference id=37643/> and antidiabetic <Reference id=37645/><Reference id=37648/> effects.
iupac name: (2Z,4E)-5-(1-hydroxy-2,6,6-trimethyl-4-oxo-1-cyclohex-2-enyl)-3-methylpenta-2,4-dienoic acid
xref: CHEMBL379808
synonym: (+/-)-Abscisic acid
synonym: (RS)-Abscisic acid
synonym: (+/-)-(cis,trans)-abscisic acid
synonym: ABA
approved: f
ligand name: abscisic acid
type: NaturalProductLigand

RG-1530
in ch i key: UOVCGJXDGOGOCZ-UHFFFAOYSA-N
in ch i: InChI=1S/C18H14ClFN4O/c1-9-16-18(24-23-9)21-14-8-15(25-2)13(20)7-11(14)17(22-16)10-5-3-4-6-12(10)19/h3-8H,1-2H3,(H2,21,23,24)
comment: RG-1530 is an orally active multikinase inhibitor, with a high affinity for polo like kinase 4 (PLK4). Its PLK4 inhibitory action was expoited for antiproliferative potential <Reference id=37606/><Reference id=37605/><Reference id=37604/><Reference id=26827/>. PLK4 is expressed at very low levels in normal cells, but its expression can be upregulated in cancer cells where it localises to the centriole and is essential for controlling centriole duplication and mitotic progression. This makes PLK4 an ideal target for disrupting mitosis in cancer cells.
iupac name: 5-(2-chlorophenyl)-7-fluoro-8-methoxy-3-methyl-2,10-dihydropyrazolo[3,4-b][1,4]benzodiazepine
xref: CHEMBL1980391
synonym: R1530
synonym: R-1530
synonym: RG1530
synonym: compound 2 [PMID: 24900658]
approved: f
ligand name: RG-1530
type: SyntheticOrganicLigand

utatrectinib
in ch i key: AYOOGWWGECJQPI-NSHDSACASA-N
in ch i: InChI=1S/C18H19FN8O/c1-10(2)28-16-6-15(25-26-16)27-9-22-13-4-5-14(24-18(13)27)23-11(3)17-20-7-12(19)8-21-17/h4-11H,1-3H3,(H,23,24)(H,25,26)/t11-/m0/s1
comment: AZD7451 is a pan tropomyosin receptor kinase (TRK; also know as neurotrophic receptor tyrosine kinases or NTRKs) inhibitor <Reference id=37600/>. It reached Phase 1 clinical development for anticancer potential, but the programme was discontinued. It was designed for the treatment of tumours that express oncogenic NTRK fusions <Reference id=37598/><Reference id=37601/>. The chemical structure of AZD7451 is identical to that which was submitted to the WHO for the INN utatrectinib (proposed INN list 126, Jan 2022).
xref: CHEMBL3659497
synonym: AZ12607092
synonym: AZD-7451
synonym: Example 6 [US8486966B2]
synonym: AZD7451
approved: f
ligand name: utatrectinib
type: SyntheticOrganicLigand

GSK065
in ch i key: WPAHVUADNLXSOM-SNVBAGLBSA-N
in ch i: InChI=1S/C17H15ClN2O4/c1-10(13-4-2-3-7-19-13)23-16-9-15-11(8-12(16)18)14(20-24-15)5-6-17(21)22/h2-4,7-10H,5-6H2,1H3,(H,21,22)/t10-/m1/s1
comment: GSK065 (a.k.a. GSK3335065) was a clinical lead kynurenine-3-monooxygenase (KMO) inhibitor that was developed for potential to treat acute pancreatitis multiple organ dysfunction syndrome (AP-MODS) <Reference id=37581/>. It was designed to be administered intravenously. The intention of inhibiting KMO is to return AP-MODS-associated elevation in 3-hydroxykynurenine levels <Reference id=37582/> to the normal range, so as to reduce acute pancreatitis-induced organ damage. GSK065 was developed though a partnership between the University of Edinburgh's Centre for Inflammation Research and GSK's Discovery Partnerships with Academia programme.
synonym: GSK3335065
synonym: inhibitor C1 [PMID: 28604669]
approved: f
ligand name: GSK065
type: SyntheticOrganicLigand

CDK inhibitor 4.35
in ch i key: PCQPAKMJSYGXRE-UHFFFAOYSA-N
in ch i: InChI=1S/C22H25N7S/c1-14(2)18-19-20(29-28-18)21(27-22(26-19)30-12-10-23)25-13-15-6-8-16(9-7-15)17-5-3-4-11-24-17/h3-9,11,14H,10,12-13,23H2,1-2H3,(H,28,29)(H,25,26,27)
comment: Compound 4.35 is a selective inhibitor of CDKs 2, 5 and 9 <Reference id=37578/>. It was designed for potential anti-lymphoma activity. Its cytotoxic effects on lymphoma cell lines are achieved via promotion of apoptosis. The co-crystal structure of 4.35 bound to CDK2/cyclin A2 has been submitted to the PBD with ID 6GVA <Reference id=37633/> and this shows that the ligand binds to the kinase active site.
iupac name: 5-[(2-aminoethyl)sulfanyl]-3-(propan-2-yl)-N-{[4-(pyridin-2-yl)phenyl]methyl}-1H-pyrazolo[4,3-d]pyrimidin-7-amine
synonym: LGR4455
approved: f
ligand name: CDK inhibitor 4.35
type: SyntheticOrganicLigand

purmorphamine
in ch i key: FYBHCRQFSFYWPY-UHFFFAOYSA-N
in ch i: InChI=1S/C31H32N6O2/c1-2-9-25(10-3-1)37-21-32-28-29(33-23-13-15-24(16-14-23)36-17-19-38-20-18-36)34-31(35-30(28)37)39-27-12-6-8-22-7-4-5-11-26(22)27/h4-8,11-16,21,25H,1-3,9-10,17-20H2,(H,33,34,35)
comment: Smo receptor agonist
iupac name: 9-cyclohexyl-N-(4-morpholin-4-ylphenyl)-2-naphthalen-1-yloxypurin-6-amine
xref: CHEMBL1221984
approved: f
ligand name: purmorphamine
type: SyntheticOrganicLigand

GNE-616
in ch i key: XQUOWYVEKSXNET-RYGJVYDSSA-N
comment: GNE-616 is an arylsulfonamide class voltage gated sodium channel inhibitor that is selective for the Nav1.7 isoform <Reference id=37573/>. This class of inhibitors are channel blockers that bind to the fourth voltage sensing domain (VSD4) of the channel and lock it into the inactivated state <Reference id=37575/><Reference id=35300/>. Nav1.7 is a mechanistic target that is being pursued for the treatment of chronic pain <Reference id=37575/><Reference id=9994/><Reference id=9995/><Reference id=37576/><Reference id=37577/>.
iupac name: (4S)-6-fluoro-4-[(2R,4S)-2-(pyridin-2-yl)-4-(trifluoromethyl)piperidin-1-yl]-N-(pyrimidin-4-yl)-3,4-dihydro-2H-1-benzopyran-7-sulfonamide
synonym: GNE616
synonym: compound 24 [PMID: 30943032]
approved: f
ligand name: GNE-616
type: SyntheticOrganicLigand

elimusertib
in ch i key: YBXRSCXGRPSTMW-CYBMUJFWSA-N
in ch i: InChI=1S/C20H21N7O/c1-13-12-28-10-9-27(13)18-11-15(17-5-8-23-26(17)2)14-3-6-21-20(19(14)24-18)16-4-7-22-25-16/h3-8,11,13H,9-10,12H2,1-2H3,(H,22,25)/t13-/m1/s1
comment: Elimusertib (BAY1895344) is a potent, highly selective and orally available ATR inhibitor. It was designed using a combination of medicinal chemistry, pharmacology, DMPK (drug metabolism and pharmacokinetics) and computational chemistry. ATR responds to a broad spectrum of DNA damage and activates the DNA damage response (DDR) pathway. By preventing DNA repair in cancer cells (which are under replication stress and suffer from increased DNA damage and defective DNA damage repair), inhibition of ATR is expected to drive the cancer cells towards cell cycle arrest and cell death <Reference id=37568/><Reference id=37796/>.
iupac name: (3R)-3-methyl-4-[4-(2-methylpyrazol-3-yl)-8-(1H-pyrazol-5-yl)-1,7-naphthyridin-2-yl]morpholine
synonym: BAY-1895344
synonym: BAY 1895344
synonym: BAY1895344
approved: f
ligand name: elimusertib
type: SyntheticOrganicLigand

AZD5718
in ch i key: ROTWSDMXHVGAHZ-QZTJIDSGSA-N
in ch i: InChI=1S/C24H26N6O3/c1-14-12-19(29-28-14)15-6-8-16(9-7-15)22(31)17-4-2-3-5-18(17)23(32)27-20-13-26-30-11-10-25-24(33)21(20)30/h6-9,12-13,17-18H,2-5,10-11H2,1H3,(H,25,33)(H,27,32)(H,28,29)/t17-,18-/m1/s1
comment: AZD5718 is an inhibitor of <Ligand id=5183/> (FLAP) that was developed by Astra Zeneca <Reference id=37552/>. It is orally active and is suitable for once-daily dosing. Initial clinical findings from a first-in-human study confirmed AZD5718 target engagement, and indicated that the compound is safe and well tolerated <Reference id=37553/>. It is being advanced for further evaluation in patients with coronary artery disease. The 5-LOX pathway has been targeted for drug development as an intervention in a number of diseases where chronic inflammation drives the pathophysiology (e.g. asthma, chronic obstructive pulmonary disease and atherosclerotic coronary artery disease). Since FLAP is a crucial regulator of 5-LOX activity, it too is being pursued as a druggable anti-inflammatory target. FLAP inhibitors and 5-LOX inhibitors reduce production of the leukotriene precursor LTA4 <Reference id=37554/><Reference id=37555/>.
iupac name: (1R,2R)-2-[4-(5-methyl-1H-pyrazol-3-yl)benzoyl]-N-(4-oxo-6,7-dihydro-5H-pyrazolo[1,5-a]pyrazin-3-yl)cyclohexane-1-carboxamide
synonym: compound 12 [PMID: 30869888]
approved: f
ligand name: AZD5718
type: SyntheticOrganicLigand

LUF7602
in ch i key: WUZBOJXXYMKMMF-UHFFFAOYSA-N
in ch i: InChI=1S/C24H26FN5O6S/c1-3-12-30-23(32)20-21(27-19-15-17(36-2)10-14-28(19)20)29(24(30)33)13-5-4-11-26-22(31)16-6-8-18(9-7-16)37(25,34)35/h6-10,14-15H,3-5,11-13H2,1-2H3,(H,26,31)
comment: LUF7602 is a covalent (i.e. irreversible) antagonist of the adenosine A3 receptor <Reference id=37551/>. The fluorosulfonyl warhead binds to amino acid residue Y265 of the receptor. LUF7602 does not bind to a mutant human A3R in which the tyrosine 265 residue is replaced by phenylalanine (Y265F), confirming this residue as the anchor site for the covalent interaction.
iupac name: 4-((3(8-Methoxy-2,4-dioxo-3-propyl-3,4-dihydropyrido[2,1-f]purin-1(2H)yl)propyl)carbamoyl)benzenesulfonyl Fluoride
synonym: compound 17b [PMID: 30869893]
synonym: LUF-7602
approved: f
ligand name: LUF7602
type: SyntheticOrganicLigand

I3MT-3
canonical SMILES: Cc1cc(=O)[nH]c(n1)SCC(=O)c1cccc2c1cccc2
isomeric SMILES: Cc1cc(=O)[nH]c(n1)SCC(=O)c1cccc2c1cccc2
in ch i key: KKPLVAUVHOSUPR-UHFFFAOYSA-N
in ch i: InChI=1S/C17H14N2O2S/c1-11-9-16(21)19-17(18-11)22-10-15(20)14-8-4-6-12-5-2-3-7-13(12)14/h2-9H,10H2,1H3,(H,18,19,21)
comment: I3MT-3 is an inhibitor of the H2S-producing enzyme, 3-mercaptopyruvate sulfurtransferase (MPST) <Reference id=36843/>.
iupac name: 4-methyl-2-(2-naphthalen-1-yl-2-oxoethyl)sulfanyl-1~{H}-pyrimidin-6-one
synonym: compound 3 [PMID: 28079151]
approved: f
ligand name: I3MT-3
type: SyntheticOrganicLigand

L760735
in ch i key: USRYEHHMJIRICK-ZNZBMKLDSA-N
in ch i: InChI=1S/C26H28F7N5O2/c1-15(17-10-18(25(28,29)30)12-19(11-17)26(31,32)33)40-24-23(16-4-6-20(27)7-5-16)38(8-9-39-24)14-22-21(13-37(2)3)34-36-35-22/h4-7,10-12,15,23-24H,8-9,13-14H2,1-3H3,(H,34,35,36)/t15-,23+,24-/m1/s1
comment: High affinity NK1 antagonist
iupac name: 1-[5-[[(2R,3S)-2-[(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethoxy]-3-(4-fluorophenyl)morpholin-4-yl]methyl]-2H-triazol-4-yl]-N,N-dimethylmethanamine
approved: f
ligand name: L760735
type: SyntheticOrganicLigand

BAY-593074
in ch i key: LWUSZIVDPJPVBW-UHFFFAOYSA-N
in ch i: InChI=1S/C18H13F6NO4S/c19-17(20,21)8-3-9-30(26,27)29-13-5-1-4-12(10-13)28-16-7-2-6-15(14(16)11-25)18(22,23)24/h1-2,4-7,10H,3,8-9H2
comment: BAY-593074 is an orally active cannabinoid receptor partial agonist <Reference id=37530/>. It is a pharmacological tool for experimental research.
xref: CHEMBL1354658
synonym: BAY 59-3074
synonym: BAY593074
synonym: BAY-59-3074
approved: f
ligand name: BAY-593074
type: SyntheticOrganicLigand

K-80003
isomeric SMILES: OC(=O)CC1=C(C)/C(=C/c2ccc(cc2)C(C)C)/c2c1cc(F)cc2
in ch i key: QCXBVGNDRYQVJO-GRSHGNNSSA-N
in ch i: InChI=1S/C22H21FO2/c1-13(2)16-6-4-15(5-7-16)10-19-14(3)20(12-22(24)25)21-11-17(23)8-9-18(19)21/h4-11,13H,12H2,1-3H3,(H,24,25)/b19-10-
comment: K-80003 ia a retinoid X receptor-α (RXRα) modulator <Reference id=37528/> that can attenuate atherosclerotic plaque progression and destabilization in the ApoE-/- mouse model. Structurally, K-80003 is an analogue of the NSAID <Ligand id=5425/>, but it lacks the COX inhibitory activity of the parent molecule <Reference id=37528/>.
iupac name: 2-[(3Z)-6-fluoro-2-methyl-3-[(4-propan-2-ylphenyl)methylidene]inden-1-yl]acetic acid
approved: f
ligand name: K-80003
type: SyntheticOrganicLigand

MK-571
isomeric SMILES: OC(=O)CCSC(c1cccc(c1)/C=C/c1ccc2c(n1)cc(cc2)Cl)SCCC(=O)N(C)C
in ch i key: AXUZQJFHDNNPFG-UXBLZVDNSA-N
comment: MK-571 is a stereo enantiomer of <Ligand id=6193/> <Reference id=37506/>. Be aware of the confusion caused by incorrectly using MK-571 as a synonym for verlukast that has arisen in online resources.
iupac name: 3-[[3-[(E)-2-(7-chloroquinolin-2-yl)ethenyl]phenyl]-(3-dimethylamino-3-oxopropyl)sulfanylmethyl]sulfanylpropanoic acid
xref: CHEMBL15177
synonym: MK571
synonym: MK 571
synonym: MK-0571
approved: f
ligand name: MK-571
type: SyntheticOrganicLigand

compound 3a [Badolato et al., 2019]
canonical SMILES: ClC1=C(N2CCOCC2)C(=O)c2c(C1=O)c(O)ccc2O
isomeric SMILES: ClC1=C(N2CCOCC2)C(=O)c2c(C1=O)c(O)ccc2O
in ch i key: FTMCZTSKCXEXCO-UHFFFAOYSA-N
in ch i: InChI=1S/C14H12ClNO5/c15-11-12(16-3-5-21-6-4-16)14(20)10-8(18)2-1-7(17)9(10)13(11)19/h1-2,17-18H,3-6H2
comment: Compound 3a has been reported as an inverse agonist of GPR55 <Reference id=37470/>. It exhibits antiproliferative activity against breast cancer cells in vitro (e.g. MDA-MB-231 IC50 2700 nM, MCF10A IC50 3700 nM).
iupac name: 6-chloro-5,8-dihydroxy-7-morpholin-4-ylnaphthalene-1,4-dione
xref: CHEMBL1987065
approved: f
ligand name: compound 3a [Badolato et al., 2019]
type: SyntheticOrganicLigand

compound 1 [Lolli et al., 2019]
in ch i key: DKXLGDJKCXEKTB-UHFFFAOYSA-N
in ch i: InChI=1S/C20H17N3O4/c1-12-15(11-17-19(24)22-27-21-17)16-10-14(26-2)8-9-18(16)23(12)20(25)13-6-4-3-5-7-13/h3-10H,11H2,1-2H3,(H,22,24)
comment: Compound 1 is a selective inhibitor of aldo-keto reductase family 1 member C3 (AKR1C3) <Reference id=37468/>. Chemically it is a biostere of <Ligand id=1909/>, but its altered structure almost completely abolishes COX inhibitory activity, rendering the molecule selective for AKR1C3. Compound 1 is indicated as a pharmacological tool to further elucidate the role of AKR1C3 in cancer.
iupac name: 4-[(1-benzoyl-5-methoxy-2-methyl-1H-indol-3-yl)methyl]-1,2,5-oxadiazol-3-ol
approved: f
ligand name: compound 1 [Lolli et al., 2019]
type: SyntheticOrganicLigand

GSK8612
in ch i key: FFPHMUIGESPOTK-UHFFFAOYSA-N
comment: GSK8612 is a selective inhibitor of Tank-binding kinase 1 (TBK1) <Reference id=37465/>. TBK1 is a noncanonical member of the IκB kinase (IKK) family that is involved in regulating signalling pathways in several physiological processes including innate immunity <Reference id=37467/><Reference id=37466/>, oncogenesis, energy homeostasis, autophagy, and neuroinflammation. TBK1 is activated downstream of TLR3/TLR4 ligand engagement, via the adaptor protein TRIF. This subsequently results in IRF3 phosphorylation and culminates in IFNβ secretion from cell types including dendritic cells and macrophages. Dysregulated TBK1 activity is associated with autoimmune disorders, hence pharmacological inhibitors are considered for the treatment of (auto)inflammatory diseases.
iupac name: 4-{[(5-bromo-2-{[3-methyl-1-(2,2,2-trifluoroethyl)-1H-pyrazol-4-yl]amino}pyrimidin-4-yl)amino]methyl}benzene-1-sulfonamide
approved: f
ligand name: GSK8612
type: SyntheticOrganicLigand

solriamfetol
canonical SMILES: NC(Cc1ccccc1)COC(=O)N
isomeric SMILES: N[C@H](Cc1ccccc1)COC(=O)N
in ch i key: UCTRAOBQFUDCSR-SECBINFHSA-N
in ch i: InChI=1S/C10H14N2O2/c11-9(7-14-10(12)13)6-8-4-2-1-3-5-8/h1-5,9H,6-7,11H2,(H2,12,13)/t9-/m1/s1
comment: Solriamfetol is a norepinephrine-dopamine reuptake inhibitor that was developed by Jazz Pharmaceuticals <Reference id=37462/>.
iupac name: [(2R)-2-amino-3-phenylpropyl] carbamate
synonym: JZP-110
synonym: JZP110
synonym: ADX-N05
synonym: ADXN05
synonym: Sunosi®
approved: t
ligand name: solriamfetol
type: SyntheticOrganicLigand

diprovocim-1
in ch i key: ABZBNXFGYUSVCJ-UYMKNZQYSA-N
in ch i: InChI=1S/C56H56N6O6/c63-51(57-47-25-39(47)33-13-5-1-6-14-33)43-29-61(30-44(43)52(64)58-48-26-40(48)34-15-7-2-8-16-34)55(67)37-21-23-38(24-22-37)56(68)62-31-45(53(65)59-49-27-41(49)35-17-9-3-10-18-35)46(32-62)54(66)60-50-28-42(50)36-19-11-4-12-20-36/h1-24,39-50H,25-32H2,(H,57,63)(H,58,64)(H,59,65)(H,60,66)/t39-,40-,41-,42-,43-,44-,45-,46-,47+,48+,49+,50+/m1/s1
comment: Diprovocim-1 is a highly potent, synthetic TLR1/TLR2 agonist <Reference id=37458/>. It is structurally disctinct from other known natural or synthetic lipoprotein TLR agonists. Mechanistically it promotes the formation of TLR2 dimers and TLR2/TLR1 heterodimers in vitro <Reference id=37459/>. The structure shown here was drawn from Morin et al. (2018) <Reference id=37458/>. PubChem hold a record for Diprovocim that shows alternative stereochemistry (CID 134817267).
synonym: compound 3 [PMID: 30272974]
approved: f
ligand name: diprovocim-1
type: SyntheticOrganicLigand

compound 58l [PMID: 30843696]
in ch i key: UDMPNYKEHCRGIV-UHFFFAOYSA-N
in ch i: InChI=1S/C23H24N4O5S/c1-15-3-5-16(6-4-15)14-33(30,31)26-22(29)23(2)7-9-27(10-8-23)20-17(12-24)11-18-19(25-20)13-32-21(18)28/h3-6,11H,7-10,13-14H2,1-2H3,(H,26,29)
comment: Compound 58l is a derivative of the P2Y12 receptor antagonist <Ligand id=7360/> that has been optimised for drug-like properties (e.g. enhanced metabolic stability and antithrombotic efficacy in vivo) <Reference id=37457/>.
iupac name: 1-(3-Cyano-5-oxo-5,7-dihydrofuro[3,4-b]pyridin-2-yl)-4-methyl-N-((4-methylbenzyl)sulfonyl)piperidine-4-carboxamide
approved: f
ligand name: compound 58l [PMID: 30843696]
type: SyntheticOrganicLigand

TCMDC-125163
in ch i key: AMPNVQJPVKIKEY-UHFFFAOYSA-N
in ch i: InChI=1S/C24H29N3O5S/c1-16-7-5-6-12-27(16)33(28,29)19-9-10-20-17(13-19)8-11-23(26-20)25-18-14-21(30-2)24(32-4)22(15-18)31-3/h8-11,13-16H,5-7,12H2,1-4H3,(H,25,26)
comment: TCMDC-125163 is a high affinity inhibitor of the P. falciparum hexose transporter (PfHT1), identified by screening the Tres Cantos antimalarial compound set (TCAMS) <Reference id=37449/>.
iupac name: 6-(2-methylpiperidin-1-yl)sulfonyl-N-(3,4,5-trimethoxyphenyl)quinolin-2-amine
xref: CHEMBL527419
approved: f
ligand name: TCMDC-125163
type: SyntheticOrganicLigand

SRI37892
in ch i key: DXSMYUKZPWJQFM-UHFFFAOYSA-N
in ch i: InChI=1S/C26H19N5O2S/c32-24-12-8-17-13-18(7-11-20(17)28-24)22-14-34-26(29-22)30-25(33)16-5-9-19(10-6-16)31-15-27-21-3-1-2-4-23(21)31/h1-7,9-11,13-15H,8,12H2,(H,28,32)(H,29,30,33)
comment: SRI37892 is a small-molecule that was identified as a FZD7 antagonist in a reporter assay screen, but its pharmacology remains to be fully validated <Reference id=37409/>.
iupac name: 4-(benzimidazol-1-yl)-N-[4-(2-oxo-3,4-dihydro-1H-quinolin-6-yl)-1,3-thiazol-2-yl]benzamide
approved: f
ligand name: SRI37892
type: SyntheticOrganicLigand

bromodiphenhydramine
canonical SMILES: CN(CCOC(c1ccc(cc1)Br)c1ccccc1)C
isomeric SMILES: CN(CCOC(c1ccc(cc1)Br)c1ccccc1)C
in ch i key: NUNIWXHYABYXKF-UHFFFAOYSA-N
in ch i: InChI=1S/C17H20BrNO/c1-19(2)12-13-20-17(14-6-4-3-5-7-14)15-8-10-16(18)11-9-15/h3-11,17H,12-13H2,1-2H3
comment: Bromazine (bromodiphenhydramine) is an antihistamine. This drug also has antimicrobial action but is known to cause drowsiness. The only information regarding approval for clinical use of this drug on the US FDA website is in a drug combination with codeine. Other national approval agencies may have granted marketing authorisation.
xref: CHEMBL1201245
synonym: Ambodryl®
approved: t
ligand name: bromodiphenhydramine
type: SyntheticOrganicLigand

Lys01
in ch i key: WDGQVCRQXSYPCW-UHFFFAOYSA-N
in ch i: InChI=1S/C23H23Cl2N5/c1-30(12-10-28-20-6-8-26-22-14-16(24)2-4-18(20)22)13-11-29-21-7-9-27-23-15-17(25)3-5-19(21)23/h2-9,14-15H,10-13H2,1H3,(H,26,28)(H,27,29)
comment: Lys01 was developed for use as an antimalarial agent <Reference id=37389/> and is also reported to be a potent inhibitor of autophagy <Reference id=37740/>.
iupac name: N-(7-chloroquinolin-4-yl)-N'-[2-[(7-chloroquinolin-4-yl)amino]ethyl]-N'-methylethane-1,2-diamine
xref: CHEMBL4282488
synonym: compound 3a [PMID: 30344903]
synonym: LYS 01
synonym: LYS-01
approved: f
ligand name: Lys01
type: SyntheticOrganicLigand

GI‐530159
in ch i key: HHLMWQDRYZAENA-UHFFFAOYSA-N
in ch i: InChI=1S/C27H20F6N2O2/c28-26(29,30)25(27(31,32)33,17-1-9-21(10-2-17)36-23-13-5-19(34)6-14-23)18-3-11-22(12-4-18)37-24-15-7-20(35)8-16-24/h1-16H,34-35H2
comment: GI‐530159 is a K2P channel activator <Reference id=37429/>.
iupac name: 4-[4-[2-[4-(4-aminophenoxy)phenyl]-1,1,1,3,3,3-hexafluoropropan-2-yl]phenoxy]aniline
approved: f
ligand name: GI‐530159
type: SyntheticOrganicLigand

BL-1249
canonical SMILES: C1CCc2c(C1)c(ccc2)Nc1ccccc1c1n[nH]nn1
isomeric SMILES: C1CCc2c(C1)c(ccc2)Nc1ccccc1c1n[nH]nn1
in ch i key: YYNRZIFBTOUICE-UHFFFAOYSA-N
in ch i: InChI=1S/C17H17N5/c1-2-8-13-12(6-1)7-5-11-15(13)18-16-10-4-3-9-14(16)17-19-21-22-20-17/h3-5,7,9-11,18H,1-2,6,8H2,(H,19,20,21,22)
comment: BL-1249 is a K2P channel activator <Reference id=37428/>. It activates K2P2.1 (TREK-1) and K2P10.1 (TREK-2) ∼10-fold more potently than K2P4.1 (TRAAK).
iupac name: N-[2-(2H-tetrazol-5-yl)phenyl]-5,6,7,8-tetrahydronaphthalen-1-amine
xref: CHEMBL1417584
synonym: BL1249
synonym: BL 1249
approved: f
ligand name: BL-1249
type: SyntheticOrganicLigand

astressin 2B
in ch i key: IVIBPRHVUKMKSX-YJHXGIRISA-N
comment: Astressin 2B is a potent and selective CRF2 antagonist <Reference id=37422/>.
synonym: cyclo(31-34)[DPhe(11),His(12),C(alpha)MeLeu(13,39),Nle(17),Glu(31),Lys(34)]Ac-sauvagine(8-40)
synonym: astressin2-B
synonym: peptide 20 [PMID: 12361401]
synonym: Astressin2-B
approved: f
ligand name: astressin 2B
type: PeptideLigand

ANTA XV
in ch i key: KSWYJUIFHPSZOL-UHFFFAOYSA-N
in ch i: InChI=1S/C27H29N5O/c1-27(2,33)21-12-13-25(28-19-21)31-14-16-32(17-15-31)26-23-11-7-6-10-22(23)24(29-30-26)18-20-8-4-3-5-9-20/h3-13,19,33H,14-18H2,1-2H3
comment: ANTA XV is a potent, orally bioavailable small-molecule SMO antagonist that was designed for antitumour potential <Reference id=37421/><Reference id=37420/>.
iupac name: 2-[6-[4-(4-benzylphthalazin-1-yl)piperazin-1-yl]pyridin-3-yl]propan-2-ol
xref: CHEMBL485870
approved: f
ligand name: ANTA XV
type: SyntheticOrganicLigand

taladegib
in ch i key: SZBGQDXLNMELTB-UHFFFAOYSA-N
in ch i: InChI=1S/C26H24F4N6O/c1-34(25(37)20-8-7-16(27)15-21(20)26(28,29)30)17-10-13-36(14-11-17)24-19-6-4-3-5-18(19)23(32-33-24)22-9-12-31-35(22)2/h3-9,12,15,17H,10-11,13-14H2,1-2H3
comment: Taladegib (LY2940680) is an orally active SMO antagonist that was developed as an antitumour agent by Eli Lilly <Reference id=37419/>.
iupac name: 4-fluoro-N-methyl-N-[1-[4-(2-methylpyrazol-3-yl)phthalazin-1-yl]piperidin-4-yl]-2-(trifluoromethyl)benzamide
xref: CHEMBL2142592
synonym: LY2940680
synonym: LY-2940680
approved: f
ligand name: taladegib
type: SyntheticOrganicLigand

MRT-92
in ch i key: TVUOHEUCOWBVRU-UHFFFAOYSA-N
in ch i: InChI=1S/C33H34N4O5/c1-21-10-17-26(35-33(34)37-32(39)25-18-28(40-2)30(42-4)29(19-25)41-3)20-27(21)36-31(38)24-15-13-23(14-16-24)12-11-22-8-6-5-7-9-22/h5-10,13-20H,11-12H2,1-4H3,(H,36,38)(H3,34,35,37,39)
comment: MRT-92 is a potent small-molecule SMO antagonist <Reference id=37417/>.
approved: f
ligand name: MRT-92
type: SyntheticOrganicLigand

SANT-2
in ch i key: VQOJFGFKIVFMDH-UHFFFAOYSA-N
in ch i: InChI=1S/C26H26ClN3O4/c1-4-32-22-13-16(14-23(33-5-2)24(22)34-6-3)26(31)28-17-11-12-19(27)18(15-17)25-29-20-9-7-8-10-21(20)30-25/h7-15H,4-6H2,1-3H3,(H,28,31)(H,29,30)
comment: SANT-2 is a potent SMO antagonist and inhibitor of Hh pathway signalling <Reference id=37415/>.
xref: CHEMBL514344
approved: f
ligand name: SANT-2
type: SyntheticOrganicLigand

SANT-1
isomeric SMILES: Cc1nn(c(c1/C=N/N1CCN(CC1)Cc1ccccc1)C)c1ccccc1
in ch i key: FOORCIAZMIWALX-JJIBRWJFSA-N
in ch i: InChI=1S/C23H27N5/c1-19-23(20(2)28(25-19)22-11-7-4-8-12-22)17-24-27-15-13-26(14-16-27)18-21-9-5-3-6-10-21/h3-12,17H,13-16,18H2,1-2H3/b24-17+
comment: SANT-1 is a potent SMO antagonist and inhibitor of Hh pathway signalling <Reference id=37415/>.
iupac name: (E)-N-(4-benzylpiperazin-1-yl)-1-(3,5-dimethyl-1-phenylpyrazol-4-yl)methanimine
xref: CHEMBL515916
synonym: Shh signaling antagonist V
approved: f
ligand name: SANT-1
type: SyntheticOrganicLigand

cyclopamine-KAAD
in ch i key: WDHRPWOAMDJICD-UHFFFAOYSA-N
in ch i: InChI=1S/C44H63N3O4/c1-29-25-39-42(47(28-29)24-23-46-40(49)13-9-6-10-22-45-41(50)17-14-32-11-7-5-8-12-32)31(3)44(51-39)21-19-35-36-16-15-33-26-34(48)18-20-43(33,4)38(36)27-37(35)30(44)2/h5,7-8,11-12,15,29,31,35-36,38-39,42H,6,9-10,13-14,16-28H2,1-4H3,(H,45,50)(H,46,49)
comment: Cyclopamine-KAAD is a synthetic derivative of the plant-derived teratogen and SMO antagonist <Ligand id=10328/> <Reference id=3366/>.
iupac name: N-[2-(3',6',10,11b-tetramethyl-3-oxospiro[1,2,4,6,6a,6b,7,8,11,11a-decahydrobenzo[a]fluorene-9,2'-3,3a,5,6,7,7a-hexahydrofuro[3,2-b]pyridine]-4'-yl)ethyl]-6-(3-phenylpropanoylamino)hexanamide
synonym: KAAD-cyclopamine
synonym: 3-keto, N-aminoethyl aminocaproyl dihydrocinnamoyl cyclopamine
approved: f
ligand name: cyclopamine-KAAD
type: SyntheticOrganicLigand

cyclopamine
in ch i key: QASFUMOKHFSJGL-LAFRSMQTSA-N
in ch i: InChI=1S/C27H41NO2/c1-15-11-24-25(28-14-15)17(3)27(30-24)10-8-20-21-6-5-18-12-19(29)7-9-26(18,4)23(21)13-22(20)16(27)2/h5,15,17,19-21,23-25,28-29H,6-14H2,1-4H3/t15-,17+,19-,20-,21-,23-,24+,25-,26-,27-/m0/s1
comment: Cyclopamine is a SMO antagonist that acts as a potent inhibitor of the Hedgehog (Hh) signaling pathway <Reference id=37416/>. It is a natural product present in the roots and rhizomes of Veratrum californicum (corn lily). Multiple structures with alternative stereochemistry are recorded in online chemistry resources.
xref: CHEMBL254129
synonym: 11-Deoxyjervine
approved: f
ligand name: cyclopamine
type: NaturalProductLigand

SAG1.3
in ch i key: VFSUUTYAEQOIMW-UHFFFAOYSA-N
in ch i: InChI=1S/C28H28ClN3OS/c1-30-22-9-11-23(12-10-22)32(28(33)27-26(29)24-7-2-3-8-25(24)34-27)18-19-5-4-6-21(17-19)20-13-15-31-16-14-20/h2-8,13-17,22-23,30H,9-12,18H2,1H3
comment: SAG1.3 is a small-molecule that was originally reported as a Smoothened (SMO) agonist <Reference id=37415/>. PubChem CID 76210627 represents an alternative stereoisomer of SAG1.3. The compound has subsequently been identified as a FZD6 partial agonist that binds within the receptor's transmembrane core <Reference id=38676/>.
iupac name: 3-chloro-N-[4-(methylamino)cyclohexyl]-N-{[3-(pyridin-4-yl)phenyl]methyl}-1-benzothiophene-2-carboxamide
synonym: SMO agonist (SAG)
synonym: compound 22 [PMID: 12391318]
synonym: Smoothened agonist
approved: f
ligand name: SAG1.3
type: SyntheticOrganicLigand

GSA-10
in ch i key: MDLUYYGRCGDKGL-UHFFFAOYSA-N
in ch i: InChI=1S/C26H30N2O5/c1-3-5-6-9-16-28-21-11-8-7-10-20(21)23(29)22(25(28)31)24(30)27-19-14-12-18(13-15-19)26(32)33-17-4-2/h7-8,10-15,29H,3-6,9,16-17H2,1-2H3,(H,27,30)
comment: GSA-10 is a small-molecule positive allosteric modulator of SMO <Reference id=37414/>.
iupac name: propyl 4-[(1-hexyl-4-hydroxy-2-oxoquinoline-3-carbonyl)amino]benzoate
xref: CHEMBL3947608
synonym: GSA10
approved: f
ligand name: GSA-10
type: SyntheticOrganicLigand

selpercatinib
in ch i key: XIIOFHFUYBLOLW-UHFFFAOYSA-N
in ch i: InChI=1S/C29H31N7O3/c1-29(2,37)18-39-24-9-25(28-21(10-30)13-33-36(28)17-24)20-5-6-26(31-12-20)34-15-22-8-23(16-34)35(22)14-19-4-7-27(38-3)32-11-19/h4-7,9,11-13,17,22-23,37H,8,14-16,18H2,1-3H3
comment: Selpercatinib (LOXO-292) is a potent, selective and orally bioavailable ATP-competitive RET kinase inhibitor that was developed by Loxo Oncology. It inhibits wild-type RET, RET fusions,and RET carrying activating mutations and acquired resistance mutations <Reference id=37383/>. This reference by Subbiah et al. contains preclinical and proof-of-concept data for LOXO-292. This compound was rationally designed to offer a novel therapeutic option for heavily pretreated, multikinase inhibitor-experienced patients whose tumours carry diverse RET alterations.
iupac name: 6-(2-hydroxy-2-methylpropoxy)-4-[6-[6-[(6-methoxypyridin-3-yl)methyl]-3,6-diazabicyclo[3.1.1]heptan-3-yl]pyridin-3-yl]pyrazolo[1,5-a]pyridine-3-carbonitrile
synonym: LY3527723
synonym: LOXO-292
synonym: LOXO292
synonym: example 163 [WO2018071447A1]
synonym: Retevmo®
approved: t
ligand name: selpercatinib
type: SyntheticOrganicLigand

beta-carboline
canonical SMILES: c1ccc2c(c1)[nH]c1c2ccnc1
isomeric SMILES: c1ccc2c(c1)[nH]c1c2ccnc1
in ch i key: AIFRHYZBTHREPW-UHFFFAOYSA-N
in ch i: InChI=1S/C11H8N2/c1-2-4-10-8(3-1)9-5-6-12-7-11(9)13-10/h1-7,13H
comment: β-carboline is a harmane type compound which acts as an inhibitor of indoleamine 2,3-dioxygenase 1 (IDO1) <Reference id=27055/>.
iupac name: 9H-Pyrido[3,4-B]indole
xref: CHEMBL275224
synonym: norharmane
synonym: carbazoline
approved: f
ligand name: beta-carboline
type: SyntheticOrganicLigand

simurosertib
in ch i key: XGVXKJKTISMIOW-ZDUSSCGKSA-N
in ch i: InChI=1S/C17H19N5OS/c1-9-11(8-18-21-9)14-7-12-15(24-14)17(23)20-16(19-12)13-6-10-2-4-22(13)5-3-10/h7-8,10,13H,2-6H2,1H3,(H,18,21)(H,19,20,23)/t13-/m0/s1
comment: Simurosertib (TAK-931) is an oral Cdc7 (cell division cycle 7-related protein kinase) inhibitor that is being developed by Millennium Pharmaceuticals/Takeda for potential antineoplastic activity in CDC7-overexpressing tumour cells <Reference id=38575/>. Cdc7 is a serine/threonine kinase and cell division cycle protein. Simurosertib sensitizes tumour cells to DNA-damaging chemotherapies by functioning to disrupt the cells' ability to recover from DNA damage <Reference id=42312/>.
iupac name: 2-[(2S)-1-azabicyclo[2.2.2]octan-2-yl]-6-(5-methyl-1H-pyrazol-4-yl)-3H-thieno[3,2-d]pyrimidin-4-one
synonym: TAK-931
synonym: TAK931
synonym: example 108 [US9655900B2]
approved: f
ligand name: simurosertib
type: SyntheticOrganicLigand

repotrectinib
in ch i key: FIKPXCOQUIZNHB-WDEREUQCSA-N
in ch i: InChI=1S/C18H18FN5O2/c1-10-8-20-18(25)14-9-21-24-6-5-16(23-17(14)24)22-11(2)13-7-12(19)3-4-15(13)26-10/h3-7,9-11H,8H2,1-2H3,(H,20,25)(H,22,23)/t10-,11+/m0/s1
comment: Repotrectinib (TPX-0005) is a next-generation oral ROS1/NTRK/ALK inhibitor that was rationally designed to overcome tumour resistance due to acquired solvent-front mutations in these kinases <Reference id=37380/>. The chemical structure is claimed as example 93 in TP Therapeutics' patent US20170334929A1 <Reference id=37381/>.
iupac name: (3R,11S)-6-fluoro-3,11-dimethyl-10-oxa-2,13,17,18,21-pentazatetracyclo[13.5.2.04,9.018,22]docosa-1(21),4(9),5,7,15(22),16,19-heptaen-14-one
synonym: TPX-0005
synonym: TPX0005
synonym: example 93 [US20170334929A1]
approved: f
ligand name: repotrectinib
type: SyntheticOrganicLigand

omidenepag
in ch i key: YHGSTSNEOJUIRN-UHFFFAOYSA-N
in ch i: InChI=1S/C23H22N6O4S/c30-23(31)15-25-22-6-1-4-19(27-22)17-28(34(32,33)21-5-2-11-24-14-21)16-18-7-9-20(10-8-18)29-13-3-12-26-29/h1-14H,15-17H2,(H,25,27)(H,30,31)
comment: Omidenepag acts as a selective agonist of the prostanoid EP2 receptor <Reference id=37378/>. It is administered as an opthalmic solution containing omidenepag isopropyl (which is named DE-117) in clinical studies <Reference id=44166/><Reference id=44165/>. Omidenepag isopropyl has PubChem CID 44230999.
iupac name: 2-[[6-[[(4-pyrazol-1-ylphenyl)methyl-pyridin-3-ylsulfonylamino]methyl]pyridin-2-yl]amino]acetic acid
xref: CHEMBL3707245
synonym: UR-7276
synonym: UR7276
synonym: Omlonti®
synonym: DE-117 (omidenepag isopropyl ophthalmic solution)
approved: t
ligand name: omidenepag
type: SyntheticOrganicLigand

selitrectinib
in ch i key: OEBIHOVSAMBXIB-SJKOYZFVSA-N
in ch i: InChI=1S/C20H21FN6O/c1-12-4-5-16-14(9-13(21)10-22-16)17-3-2-7-26(17)18-6-8-27-19(25-18)15(11-23-27)20(28)24-12/h6,8-12,17H,2-5,7H2,1H3,(H,24,28)/t12-,17-/m1/s1
comment: Selitrectinib (LOXO-195) is an oral tyrosine kinase inhibitor that is being developed by Loxo Oncology for antineoplastic potential <Reference id=37571/>. Mechanistically it is a selective neurotrophic receptor tyrosine kinase (NTRK) inhibitor that is designed to overcome acquired resistance caused by kinase domain mutations in NTRK fusion-positive tumours.
iupac name: (6R,15R)-9-fluoro-15-methyl-2,11,16,20,21,24-hexazapentacyclo[16.5.2.02,6.07,12.021,25]pentacosa-1(24),7(12),8,10,18(25),19,22-heptaen-17-one
synonym: LOXO-195
synonym: LOXO195
synonym: example 28 [WO2017075107A1]
synonym: BAY 2731954
synonym: BAY-2731954
approved: f
ligand name: selitrectinib
type: SyntheticOrganicLigand

lerociclib
in ch i key: YPJRHEKCFKOVRT-UHFFFAOYSA-N
in ch i: InChI=1S/C26H34N8O/c1-18(2)32-10-12-33(13-11-32)20-6-7-22(27-16-20)30-25-28-15-19-14-21-24(35)29-17-26(8-4-3-5-9-26)34(21)23(19)31-25/h6-7,14-16,18H,3-5,8-13,17H2,1-2H3,(H,29,35)(H,27,28,30,31)
comment: Lerociclib (G1T38) is an investigational CDK4/6 inhibitor <Reference id=37373/>. It is being developed to help protect non-cancerous (normal) cells (in particular, hematopoietic stem and progenitor cells, and renal cells) in patients who are undergoing DNA damaging cancer chemotherapy <Reference id=37374/>. Lerociclib was designed to be highly selective, and short and transiently-acting.
iupac name: 4-[[5-(4-propan-2-ylpiperazin-1-yl)pyridin-2-yl]amino]spiro[1,3,5,11-tetrazatricyclo[7.4.0.02,7]trideca-2,4,6,8-tetraene-13,1'-cyclohexane]-10-one
xref: CHEMBL3904602
synonym: G1T38
synonym: G1T-38
synonym: example GG [US9464092B2]
approved: f
ligand name: lerociclib
type: SyntheticOrganicLigand

CYM-50358
in ch i key: QWJOPXDAQCDRRM-UHFFFAOYSA-N
comment: Potent and selective S1P4 antagonist.
iupac name: N-[4-(aminomethyl)-2,6-dimethylphenyl]-5-(2,5-dichlorophenyl)furan-2-carboxamide
synonym: CYM 50358
synonym: CYM50358
approved: f
ligand name: CYM-50358
type: SyntheticOrganicLigand

CYM-50308
isomeric SMILES: COCCN=C1S/C(=C/c2cc(n(c2C)c2ccc(cc2F)F)C)/C(=O)N1C
in ch i key: BKQZKTRCUAWRHT-ONBPWHQPSA-N
comment: Potent and selective sphingosine-1-phosphate receptor 4 (S1P4) agonist.
iupac name: (5Z)-5-[[1-(2,4-difluorophenyl)-2,5-dimethylpyrrol-3-yl]methylidene]-2-(2-methoxyethylimino)-3-methyl-1,3-thiazolidin-4-one
synonym: CYM 50308
synonym: CYM50308
approved: f
ligand name: CYM-50308
type: SyntheticOrganicLigand

TY-52156
in ch i key: XONRRGIRSGNWFP-UHFFFAOYSA-N
in ch i: InChI=1S/C18H19Cl2N3O/c1-18(2,3)16(24)17(21-14-8-4-12(19)5-9-14)23-22-15-10-6-13(20)7-11-15/h4-11,22H,1-3H3,(H,21,23)
comment: S1P3 receptor antagonist.
iupac name: N-(4-chloroanilino)-N'-(4-chlorophenyl)-3,3-dimethyl-2-oxobutanimidamide
synonym: TY 52156
synonym: TY52156
approved: f
ligand name: TY-52156
type: SyntheticOrganicLigand

RP-001
in ch i key: WNDDDFYFTSGSEC-UHFFFAOYSA-N
in ch i: InChI=1S/C24H24N4O4/c1-14(2)31-21-9-6-15(12-16(21)13-25)24-27-23(28-32-24)19-5-3-4-18-17(19)7-8-20(18)26-11-10-22(29)30/h3-6,9,12,14,20,26H,7-8,10-11H2,1-2H3,(H,29,30)
comment: Orthosteric, short-duration S1P1 selective agonist.
iupac name: 3-[[4-[5-(3-cyano-4-propan-2-yloxyphenyl)-1,2,4-oxadiazol-3-yl]-2,3-dihydro-1H-inden-1-yl]amino]propanoic acid
synonym: RP001
approved: f
ligand name: RP-001
type: SyntheticOrganicLigand

diminazene
canonical SMILES: NC(=N)c1ccc(cc1)NN=Nc1ccc(cc1)C(=N)N
isomeric SMILES: NC(=N)c1ccc(cc1)NN=Nc1ccc(cc1)C(=N)N
in ch i key: XNYZHCFCZNMTFY-UHFFFAOYSA-N
in ch i: InChI=1S/C14H15N7/c15-13(16)9-1-5-11(6-2-9)19-21-20-12-7-3-10(4-8-12)14(17)18/h1-8H,(H3,15,16)(H3,17,18)(H,19,20)
comment: Administered as diminazene aceturate (CID 5284544), this is a is a trypanocidal agent that has been used in veterinary practice since 1955.
xref: CHEMBL35241
synonym: Berenil®
synonym: Pirocide®
synonym: Azidin®
approved: f
ligand name: diminazene
type: SyntheticOrganicLigand

RN-9893
in ch i key: KORKKQLDGMHNKO-UHFFFAOYSA-N
comment: RN-9893 is an orally-bioavailable, selective inhibitor/antagonist of the TRPV4 ion channel <Reference id=37331/>. It inhibits the channel activity of the human, rat and murine variants of TRPV4, and is selective for TRPV4 compared to related TRP channels, including TRPV1, TRPV3 and TRPM8. RN-9893 is therefore an appropriate probe compound for in vivo applications.
iupac name: 2-nitro-N-[4-(4-propan-2-ylpiperazin-1-yl)sulfonylphenyl]-4-(trifluoromethyl)benzamide
xref: CHEMBL3613642
synonym: compound 26 [PMID: 26235950]
synonym: RN9893
approved: f
ligand name: RN-9893
type: SyntheticOrganicLigand

HC-070
in ch i key: VYJPVPHNGWEIBT-UHFFFAOYSA-N
comment: HC-070 is a potent, small molecule antagonist/channel blocker of TRPC4 and TRPC5 <Reference id=37282/>.
iupac name: 8-(3-chlorophenoxy)-7-[(4-chlorophenyl)methyl]-1-(3-hydroxypropyl)-3-methylpurine-2,6-dione
approved: f
ligand name: HC-070
type: SyntheticOrganicLigand

forsythoside B
in ch i key: JMBINOWGIHWPJI-UNSOMVRXSA-N
in ch i: InChI=1S/C34H44O19/c1-15-24(41)25(42)26(43)32(50-15)53-29-27(44)31(47-9-8-17-3-6-19(37)21(39)11-17)51-22(12-48-33-30(45)34(46,13-35)14-49-33)28(29)52-23(40)7-4-16-2-5-18(36)20(38)10-16/h2-7,10-11,15,22,24-33,35-39,41-46H,8-9,12-14H2,1H3/b7-4+/t15-,22+,24-,25+,26+,27+,28+,29+,30-,31+,32-,33+,34+/m0/s1
comment: Forsythoside B is a naturallt occurring compound found in Lamiophlomis rotata Kudo plants. It has demonstrated in vivo antipruritic activity via inhibition of the thermosensitive TRPV3 ion channel in the skin <Reference id=37330/>. Chemically it is a phenylethanoid glycoside.
iupac name: [(2R,3R,4R,5R,6R)-2-[[(2R,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxymethyl]-6-[2-(3,4-dihydroxyphenyl)ethoxy]-5-hydroxy-4-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-3-yl] (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
approved: f
ligand name: forsythoside B
type: NaturalProductLigand

osthole
canonical SMILES: COc1ccc2c(c1CC=C(C)C)oc(=O)cc2
isomeric SMILES: COc1ccc2c(c1CC=C(C)C)oc(=O)cc2
in ch i key: MBRLOUHOWLUMFF-UHFFFAOYSA-N
in ch i: InChI=1S/C15H16O3/c1-10(2)4-7-12-13(17-3)8-5-11-6-9-14(16)18-15(11)12/h4-6,8-9H,7H2,1-3H3
comment: Osthole is a bioactive natural botanical compound with anti-fungal and antipruritic activities. It is a reported TRPV3 channel blocker <Reference id=37329/>.
iupac name: 7-methoxy-8-(3-methylbut-2-enyl)chromen-2-one
xref: CHEMBL52229
synonym: osthol
synonym: 7-Methoxy-8-isopentenylcoumarin
approved: f
ligand name: osthole
type: NaturalProductLigand

PF-05105679
in ch i key: BXNMZRPTQFVRFA-QGZVFWFLSA-N
in ch i: InChI=1S/C26H21FN2O3/c1-17(19-9-11-23(27)12-10-19)29(16-18-5-4-7-21(13-18)26(31)32)25(30)22-14-20-6-2-3-8-24(20)28-15-22/h2-15,17H,16H2,1H3,(H,31,32)/t17-/m1/s1
comment: PF-05105679 is a selective inhibitor of TRPM8 ion channel activity <Reference id=37321/>.
iupac name: 3-[[[(1R)-1-(4-fluorophenyl)ethyl]-(quinoline-3-carbonyl)amino]methyl]benzoic acid
xref: CHEMBL3577885
synonym: PF 05105679
synonym: PF05105679
approved: f
ligand name: PF-05105679
type: SyntheticOrganicLigand

isosakuranetin
canonical SMILES: COc1ccc(cc1)C1CC(=O)c2c(O1)cc(cc2O)O
in ch i key: HMUJXQRRKBLVOO-AWEZNQCLSA-N
in ch i: InChI=1S/C16H14O5/c1-20-11-4-2-9(3-5-11)14-8-13(19)16-12(18)6-10(17)7-15(16)21-14/h2-7,14,17-18H,8H2,1H3/t14-/m0/s1
comment: Isosakuranetin is a citrus fruit flavanone. It acts as an inhibitor of TRPM3 ion channel activity <Reference id=37314/>.
iupac name: (2S)-5,7-dihydroxy-2-(4-methoxyphenyl)-2,3-dihydrochromen-4-one
xref: CHEMBL470266
synonym: naringenin 4'-methyl ether
synonym: 4'-Methylnaringenin
approved: f
ligand name: isosakuranetin
type: NaturalProductLigand

CIM0216
in ch i key: DBBFLQPLKOEUQN-UHFFFAOYSA-N
in ch i: InChI=1S/C21H23N3O2/c1-15-14-19(23-26-15)22-21(25)20(17-9-3-2-4-10-17)24-13-7-11-16-8-5-6-12-18(16)24/h2-6,8-10,12,15,20H,7,11,13-14H2,1H3,(H,22,23,25)
comment: CIM0216 is a synthetic TRPM3 ion channel activator <Reference id=37307/>.
iupac name: N-(5-methyl-4,5-dihydro-1,2-oxazol-3-yl)-2-phenyl-2-(1,2,3,4-tetrahydroquinolin-1-yl)acetamide
synonym: CIM-0216
approved: f
ligand name: CIM0216
type: SyntheticOrganicLigand

compound 31 [PMID: 29968758]
canonical SMILES: [O-]C(=O)CC(C(=O)[O-])NC(=O)c1cccc(n1)c1ccc(cc1)OC(F)(F)F
isomeric SMILES: [O-]C(=O)C[C@@H](C(=O)[O-])NC(=O)c1cccc(n1)c1ccc(cc1)OC(F)(F)F
in ch i key: TUTOXIPIHTUWDS-ZDUSSCGKSA-L
in ch i: InChI=1S/C17H13F3N2O6/c18-17(19,20)28-10-6-4-9(5-7-10)11-2-1-3-12(21-11)15(25)22-13(16(26)27)8-14(23)24/h1-7,13H,8H2,(H,22,25)(H,23,24)(H,26,27)/p-2/t13-/m0/s1
comment: Agonist for the succinate receptor.
iupac name: (2S)-2-({6-[4-(trifluoromethoxy)phenyl]pyridin-2-yl}formamido)butanedioate
synonym: Trifluoromethoxy)phenyl)picolinoyl)-L-aspartic acid
approved: f
ligand name: compound 31 [PMID: 29968758]
type: SyntheticOrganicLigand

larixyl acetate
in ch i key: CFEOXVWJRPHLSF-UHFFFAOYSA-N
in ch i: InChI=1S/C24H38O4/c1-9-23(7,28-18(4)26)14-11-19-16(2)15-20(27-17(3)25)21-22(5,6)12-10-13-24(19,21)8/h9,19-21H,1-2,10-15H2,3-8H3
comment: Larixyl acetate is a naturally occurring constituent of larch resin. It has been reported as a potent TRPC6 ion channel inhibitor <Reference id=37303/>.
iupac name: [(4aS)-4-(3-acetyloxy-3-methylpent-4-enyl)-4a,8,8-trimethyl-3-methylidene-2,4,5,6,7,8a-hexahydro-1H-naphthalen-1-yl] acetate
approved: f
ligand name: larixyl acetate
type: SyntheticOrganicLigand

compound 130 [PMID: 29157600]
in ch i key: DXDJHKUZMNAXTM-JTQLQIEISA-N
in ch i: InChI=1S/C15H12FNO6/c16-9-3-1-8(2-4-9)11-5-6-12(23-11)14(20)17-10(15(21)22)7-13(18)19/h1-6,10H,7H2,(H,17,20)(H,18,19)(H,21,22)/t10-/m0/s1
comment: Agonist for the succinate receptor.
iupac name: (2S)-2-{[5-(4-fluorophenyl)furan-2-yl]formamido}butanedioic acid
synonym: (5-(4-Fluorophenyl)furan-2-carbonyl)-L-aspartic acid
approved: f
ligand name: compound 130 [PMID: 29157600]
type: SyntheticOrganicLigand

polygodial
canonical SMILES: O=CC1C(=CCC2C1(C)CCCC2(C)C)C=O
in ch i key: AZJUJOFIHHNCSV-KCQAQPDRSA-N
in ch i: InChI=1S/C15H22O2/c1-14(2)7-4-8-15(3)12(10-17)11(9-16)5-6-13(14)15/h5,9-10,12-13H,4,6-8H2,1-3H3/t12-,13-,15+/m0/s1
comment: Polygodial is a naturally occurring drimane sesquiterpene family aldehyde compound that is synthesized by plants and animals, often as a noxious natural deterrent. It elicits its pungent/irritant effects via activation of the TRPA1 ion channel <Reference id=21417/>
iupac name: (1R,4aS,8aS)-5,5,8a-trimethyl-1,4,4a,6,7,8-hexahydronaphthalene-1,2-dicarbaldehyde
xref: CHEMBL254550
approved: f
ligand name: polygodial
type: SyntheticOrganicLigand

AM12
canonical SMILES: Oc1cc(O)c2c(c1)oc(c(c2=O)O)c1ccccc1Br
isomeric SMILES: Oc1cc(O)c2c(c1)oc(c(c2=O)O)c1ccccc1Br
in ch i key: OVIAJBSVWWYJSD-UHFFFAOYSA-N
in ch i: InChI=1S/C15H9BrO5/c16-9-4-2-1-3-8(9)15-14(20)13(19)12-10(18)5-7(17)6-11(12)21-15/h1-6,17-18,20H
comment: AM12 is a synthetic derivative of the naturally occurring flavonol <Ligand id=410/>. Like galangin it inhibits TRPC5-mediated calcium entry in to cells <Reference id=37293/>.
iupac name: 2-(2-bromophenyl)-3,5,7-trihydroxy-4H-chromen-4-one
synonym: 3,5,7-trihydroxy-2-(2-bromophenyl)-4H-chromen-4-one
synonym: AM-12
approved: f
ligand name: AM12
type: SyntheticOrganicLigand

Pico145
in ch i key: PRJHEJGMSOBHTO-UHFFFAOYSA-N
comment: Pico145 is a potent, selective, and subtype-specific small-molecule inhibitor of TRPC1/4/5 channels <Reference id=37298/>. It competitively inhibits <Ligand id=10421/>-induced TRPC5 activation <Reference id=37932/>.
iupac name: 7-[(4-chlorophenyl)methyl]-1-(3-hydroxypropyl)-3-methyl-8-[3-(trifluoromethoxy)phenoxy]purine-2,6-dione
synonym: compound 31 [PMID: 28325835]
synonym: C31
approved: f
ligand name: Pico145
type: SyntheticOrganicLigand

AC1903
canonical SMILES: c1ccc(cc1)Cn1c(NCc2ccco2)nc2c1cccc2
isomeric SMILES: c1ccc(cc1)Cn1c(NCc2ccco2)nc2c1cccc2
in ch i key: OECUWHDVQIITIS-UHFFFAOYSA-N
in ch i: InChI=1S/C19H17N3O/c1-2-7-15(8-3-1)14-22-18-11-5-4-10-17(18)21-19(22)20-13-16-9-6-12-23-16/h1-12H,13-14H2,(H,20,21)
comment: AC1903 is small-molecule inhibitor of TRPC5 ion channels that has demonstrated in vivo activity <Reference id=37295/>.
iupac name: 1-benzyl-N-(furan-2-ylmethyl)benzimidazol-2-amine
xref: CHEMBL1345058
synonym: AC-1903
approved: f
ligand name: AC1903
type: SyntheticOrganicLigand

BTD
in ch i key: YXADKMPRWFBOHW-UHFFFAOYSA-N
in ch i: InChI=1S/C24H33N3O4S/c1-16-3-4-21-20(9-16)26-22(27-32(21,29)30)5-6-23(28)25-7-2-8-31-24-13-17-10-18(14-24)12-19(11-17)15-24/h3-4,9,17-19H,2,5-8,10-15H2,1H3,(H,25,28)(H,26,27)
comment: BTD acts as an activator of the TRPC5 ion channel <Reference id=37288/>. BTD-induced activation is long lasting, reversible and sensitive to the TRPC5 inhibitor <Ligand id=10285/>.
iupac name: N-[3-(1-adamantyloxy)propyl]-3-(6-methyl-1,1-dioxo-4H-1λ6,2,4-benzothiadiazin-3-yl)propanamide
synonym: K261-1567
approved: f
ligand name: BTD
type: SyntheticOrganicLigand

M084
canonical SMILES: CCCCNc1nc2c([nH]1)cccc2
isomeric SMILES: CCCCNc1nc2c([nH]1)cccc2
in ch i key: OKKUCNXCFWODOE-UHFFFAOYSA-N
in ch i: InChI=1S/C11H15N3/c1-2-3-8-12-11-13-9-6-4-5-7-10(9)14-11/h4-7H,2-3,8H2,1H3,(H2,12,13,14)
comment: M084 is a potent inhibitor of TRPC4 and TRPC5, and a weak inhibitor of TRPC3 <Reference id=37284/>. It is a good pharmaceutical tool for investigating the physiological and pathophysiological functions of TRPC4/C5 channels.
iupac name: N-butyl-1H-benzimidazol-2-amine
xref: CHEMBL1376358
synonym: M-084
approved: f
ligand name: M084
type: SyntheticOrganicLigand

tonantzitlolone
in ch i key: YMEAIOHYSIGDJY-VDLZEVDKSA-N
in ch i: InChI=1S/C26H40O7/c1-8-15(2)13-20(27)31-22-17(4)14-18-21(28)16(3)9-11-24(5,6)19-10-12-25(7,33-19)23(29)26(22,30)32-18/h9,11,13,16-19,22-23,29-30H,8,10,12,14H2,1-7H3/b11-9-,15-13+/t16-,17+,18+,19-,22+,23-,25+,26-/m0/s1
comment: Tonantzitlolone is a natural product with effects similar to <Ligand id=8372/>. Like (-)-englerin A the effects of tonantzitlolone appear to mediated by activation of cation flux via TRPC ion channels, principally the TRPC1/4/5 channel subtypes <Reference id=37283/>.
iupac name: [(1R,2S,3R,6S,8Z,10S,12R,14R,15R)-1,2-dihydroxy-3,7,7,10,14-pentamethyl-11-oxo-16,17-dioxatricyclo[10.3.1.13,6]heptadec-8-en-15-yl] (E)-3-methylpent-2-enoate
approved: f
ligand name: tonantzitlolone
type: NaturalProductLigand

GSK2833503A
in ch i key: ODUIXUGXPFKQLG-QWRGUYRKSA-N
comment: GSK2833503A is a TRPC3/6 ion channel blocker <Reference id=37272/>.
synonym: GSK255B
synonym: example 19 [PMID: 23886683]
approved: f
ligand name: GSK2833503A
type: SyntheticOrganicLigand

SAR7334
in ch i key: RLKRLNQEXBPQGQ-OZOXKJRCSA-N
in ch i: InChI=1S/C21H22ClN3O/c22-18-10-14(12-23)7-8-20(18)26-21-17-6-2-1-4-15(17)11-19(21)25-9-3-5-16(24)13-25/h1-2,4,6-8,10,16,19,21H,3,5,9,11,13,24H2/t16-,19-,21-/m1/s1
comment: SAR7334 blocks calcium entry via TRPC6, TRPC3 and TRPC7 ion channels <Reference id=37277/>.
iupac name: 4-[[(1R,2R)-2-[(3R)-3-aminopiperidin-1-yl]-2,3-dihydro-1H-inden-1-yl]oxy]-3-chlorobenzonitrile
synonym: SAR-7334
approved: f
ligand name: SAR7334
type: SyntheticOrganicLigand

Pyr10
in ch i key: CVALMMCIOLXHDM-UHFFFAOYSA-N
comment: Pyr10 is a pyrazole-derived compound that acts as a transient receptor potential cation channel 3 (TRPC3) blocker <Reference id=37275/>. It can be used to discriminate between TRPC and Orai-mediated Ca2+ entry.
iupac name: N-[4-[3,5-bis(trifluoromethyl)pyrazol-1-yl]phenyl]-4-methylbenzenesulfonamide
synonym: Pyr-10
approved: f
ligand name: Pyr10
type: SyntheticOrganicLigand

pyrazolopyrimidine 4n
in ch i key: JCCIFATWQJZIDU-UHFFFAOYSA-N
in ch i: InChI=1S/C22H23F3N4O3/c1-3-32-21(31)28-10-8-14(9-11-28)17-12-18(30)29-20(26-17)19(13(2)27-29)15-4-6-16(7-5-15)22(23,24)25/h4-7,12,14,30H,3,8-11H2,1-2H3
comment: Pyrazolopyrimidine 4n was discovered as the most potent analogue in a SAR campaign to identify novel activators of the TRPC3/6/7 cation channels <Reference id=37273/>.
iupac name: ethyl 4-[2-methyl-7-oxo-3-[4-(trifluoromethyl)phenyl]-1H-pyrazolo[1,5-a]pyrimidin-5-yl]piperidine-1-carboxylate
approved: f
ligand name: pyrazolopyrimidine 4n
type: SyntheticOrganicLigand

Cp-1
in ch i key: FIINKDGVMNTVCW-BKMJKUGQSA-N
in ch i: InChI=1S/C28H30F3N3O3/c1-32-27(35)26(19-7-5-4-6-8-19)34-14-13-20-15-23(36-2)24(37-3)16-21(20)22(34)11-9-18-10-12-25(33-17-18)28(29,30)31/h4-8,10,12,15-17,22,26H,9,11,13-14H2,1-3H3,(H,32,35)/t22-,26+/m0/s1
comment: Weakly OX2-selective antagonist.
iupac name: (2R)-2-[(1S)-6,7-dimethoxy-1-[2-[6-(trifluoromethyl)-2-tritiopyridin-3-yl]ethyl]-3,4-dihydro-1H-isoquinolin-2-yl]-N-methyl-2-(2-tritiophenyl)acetamide
approved: f
ligand name: Cp-1
type: SyntheticOrganicLigand

EMD-386088
canonical SMILES: Clc1ccc2c(c1)c(C1=CCNCC1)c([nH]2)C
isomeric SMILES: Clc1ccc2c(c1)c(C1=CCNCC1)c([nH]2)C
in ch i key: BPPGPYJBCVXILI-UHFFFAOYSA-N
in ch i: InChI=1S/C14H15ClN2/c1-9-14(10-4-6-16-7-5-10)12-8-11(15)2-3-13(12)17-9/h2-4,8,16-17H,5-7H2,1H3
comment: This compound was discovered as the result of a medicinal chemistry programme directed towards the design and synthesis of new tool compounds which are potent and selective 5-HT6 receptor agonists <Reference id=27959/>. Such a tool compound could be used to investigate the in vivo functional role of 5-HT6 receptors.
iupac name: 5-chloro-2-methyl-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole
xref: CHEMBL364005
synonym: compound 18 [PMID 16055331]
synonym: EMD 386088
synonym: EMD386088
approved: f
ligand name: EMD-386088
type: SyntheticOrganicLigand

GSK417651A
in ch i key: NTXBDULODNTCKP-UHFFFAOYSA-N
in ch i: InChI=1S/C20H19N3O2S/c1-25-17-8-6-16(7-9-17)21-20-22-18(13-26-20)19(24)23-11-10-14-4-2-3-5-15(14)12-23/h2-9,13H,10-12H2,1H3,(H,21,22)
comment: GSK417651A acts as a TRPC3/6 ion channel blocker <Reference id=37272/><Reference id=37268/>.
iupac name: N-(4-methoxyphenyl)-4-(1,2,3,4-tetrahydroisoquinoline-2-carbonyl)-1,3-thiazol-2-amine
xref: CHEMBL1506485
synonym: compound 3 [PMID: 23886683]
approved: f
ligand name: GSK417651A
type: SyntheticOrganicLigand

GSK1702934A
in ch i key: AXWRAIIIBRLXBP-UHFFFAOYSA-N
in ch i: InChI=1S/C22H25N3O2S/c26-21(20-14-15-6-2-1-3-9-19(15)28-20)24-12-10-16(11-13-24)25-18-8-5-4-7-17(18)23-22(25)27/h4-5,7-8,14,16H,1-3,6,9-13H2,(H,23,27)
comment: GSK1702934A acts as a TRPC3/TRPC6 channel activator/agonist <Reference id=37268/> (structure obtained from <Reference id=37267/>).
iupac name: 3-[1-(5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-2-carbonyl)piperidin-4-yl]-1H-benzimidazol-2-one
approved: f
ligand name: GSK1702934A
type: SyntheticOrganicLigand

YNT-185
in ch i key: BXJSAMKIFDDLGI-UHFFFAOYSA-N
in ch i: InChI=1S/C33H37N5O5S/c1-37(2)29-15-7-6-14-28(29)32(39)35-19-18-34-26-12-9-13-27(22-26)36-44(41,42)31-21-24(16-17-30(31)43-5)23-10-8-11-25(20-23)33(40)38(3)4/h6-17,20-22,34,36H,18-19H2,1-5H3,(H,35,39)
comment: Non-peptide Orexin receptor 2 agonist.
synonym: compound 30 [PMID: 26267383]
synonym: Nag 30
approved: f
ligand name: YNT-185
type: SyntheticOrganicLigand

AM-0902
in ch i key: AWJBWNUUODWOKQ-UHFFFAOYSA-N
in ch i: InChI=1S/C17H15ClN6O2/c1-23-9-19-16-15(23)17(25)24(10-20-16)8-14-21-13(22-26-14)7-4-11-2-5-12(18)6-3-11/h2-3,5-6,9-10H,4,7-8H2,1H3
comment: AM-0902 acts as an antagonist of the TRPA1 cation channel <Reference id=37265/>. It has demonstrated blockade of activation of human and rat TRPA1 channels, and can be used to investigate TRPA1 function in vitro and in vivo.
iupac name: 1-[[3-[2-(4-chlorophenyl)ethyl]-1,2,4-oxadiazol-5-yl]methyl]-7-methylpurin-6-one
xref: CHEMBL3785736
synonym: AM0902
synonym: compound 27 [PMID: 26942860]
approved: f
ligand name: AM-0902
type: SyntheticOrganicLigand

JT010
canonical SMILES: COCCCN(c1scc(n1)c1ccc(cc1)OC)C(=O)CCl
isomeric SMILES: COCCCN(c1scc(n1)c1ccc(cc1)OC)C(=O)CCl
in ch i key: KZMAWJRXKGLWGS-UHFFFAOYSA-N
comment: JT010 is a selective activator of the TRPA1 cation channel <Reference id=37263/>. It opens the channel by covalently and site-selectively binding to Cys621 of the protein, a mechanism that is mediated by the compound's chloroacetyl group.
synonym: molecule 1 [PMID: 26630251]
synonym: JT-010
synonym: JT 010
approved: f
ligand name: JT010
type: SyntheticOrganicLigand

ASP7663
canonical SMILES: CC(CN1C(=O)C(=CC(=O)O)c2c1c(F)ccc2)C
isomeric SMILES: CC(CN1C(=O)/C(=C/C(=O)O)/c2c1c(F)ccc2)C
in ch i key: RCVZUIGCNAAMIC-UXBLZVDNSA-N
in ch i: InChI=1S/C14H14FNO3/c1-8(2)7-16-13-9(4-3-5-11(13)15)10(14(16)19)6-12(17)18/h3-6,8H,7H2,1-2H3,(H,17,18)/b10-6+
comment: ASP7663 is a selective activator of the TRPA1 ion channel <Reference id=37262/>. It activates human, rat, and mouse channels with similar EC50 values in vitro, and is effective by oral administration in rodent models of drug-induced constipation and abdominal pain.
iupac name: (2E)-2-[7-fluoro-1-(2-methylpropyl)-2-oxoindol-3-ylidene]acetic acid
xref: CHEMBL1082283
synonym: ASP-7663
synonym: ASP 7663
approved: f
ligand name: ASP7663
type: SyntheticOrganicLigand

compound C2 [PMID: 29990428]
in ch i key: NSGDYZCDUPSTQT-UHFFFAOYSA-N
comment: C2 is a positive allosteric modulator (PAM) that targets CB2 receptors. It has reported antinociceptive efficacy in an animal model of neuropathic pain <Reference id=37261/>.
iupac name: N-{5-bromo-1-[(4-fluorophenyl)methyl]-4-methyl-2-oxo-1,2-dihydropyridin-3-yl}cycloheptanecarboxamide
synonym: Ec2la
approved: f
ligand name: compound C2 [PMID: 29990428]
type: SyntheticOrganicLigand

GAT211
in ch i key: OHZDCJJHWPHZJD-UHFFFAOYSA-N
in ch i: InChI=1S/C22H18N2O2/c25-24(26)15-19(16-9-3-1-4-10-16)21-18-13-7-8-14-20(18)23-22(21)17-11-5-2-6-12-17/h1-14,19,23H,15H2
comment: GAT211 is an agonist and positive allosteric modulator (ago-PAM) of cannabinoid receptor 1 (CB1R) and is a racemic mixture of GAT228 (R-enantiomer) and GAT229 (S-enantiomer), each of which contribute different components of GAT211's molecular pharmacology. GAT228 provides the CB1R partial agonist activity, whereas PAM activity resides with GAT229 <Reference id=37257/>.
iupac name: 3-(2-nitro-1-phenylethyl)-2-phenyl-1H-indole
approved: f
ligand name: GAT211
type: SyntheticOrganicLigand

BMS-986120
in ch i key: MINMDCMSHDBHKG-UHFFFAOYSA-N
in ch i: InChI=1S/C23H23N5O5S2/c1-13-17(25-21(34-13)27-4-6-31-7-5-27)12-32-18-8-14(29-2)9-19-15(18)10-20(33-19)16-11-28-22(24-16)35-23(26-28)30-3/h8-11H,4-7,12H2,1-3H3
comment: Orally active, selective, and reversible protease-activated receptor 4 (PAR4) antagonist <Reference id=43808/>. BMS-986120 is an antiplatelet clinical candidate.
iupac name: 4-[4-[[6-methoxy-2-(2-methoxyimidazo[2,1-b][1,3,4]thiadiazol-6-yl)-1-benzofuran-4-yl]oxymethyl]-5-methyl-1,3-thiazol-2-yl]morpholine
synonym: BMS986120
synonym: compound 43 [PMID: 35729784]
approved: f
ligand name: BMS-986120
type: SyntheticOrganicLigand

I-191
in ch i key: DTASTQAQBOZSRR-UHFFFAOYSA-N
in ch i: InChI=1S/C23H26FN5O2/c1-22(2,3)16-12-17(14-6-8-15(24)9-7-14)27-29-13-18(26-19(16)29)20(30)28-11-10-25-21(31)23(28,4)5/h6-9,12-13H,10-11H2,1-5H3,(H,25,31)
comment: Potent PAR2 antagonist that inhibits multiple PAR2-induced signaling pathways and functional responses.
iupac name: 4-[8-tert-butyl-6-(4-fluorophenyl)imidazo[1,2-b]pyridazine-2-carbonyl]-3,3-dimethylpiperazin-2-one
approved: f
ligand name: I-191
type: SyntheticOrganicLigand

rac-BHFF
in ch i key: RVNOANDLZIIFHB-UHFFFAOYSA-N
in ch i: InChI=1S/C17H21F3O3/c1-14(2,3)9-7-10(15(4,5)6)12-11(8-9)16(22,13(21)23-12)17(18,19)20/h7-8,22H,1-6H3
comment: Positive allosteric modulator of the GABAB receptor.
iupac name: 5,7-ditert-butyl-3-hydroxy-3-(trifluoromethyl)-1-benzofuran-2-one
synonym: (R,S)-5,7-di-tert-butyl-3-hydroxy-3-trifluoromethyl-3H-benzofuran-2-one
synonym: rac-BHFF
approved: f
ligand name: rac-BHFF
type: SyntheticOrganicLigand

borneol
canonical SMILES: OC1CC2C(C1(C)CC2)(C)C
isomeric SMILES: O[C@H]1C[C@@H]2C([C@@]1(C)CC2)(C)C
in ch i key: DTGKSKDOIYIVQL-WEDXCCLWSA-N
in ch i: InChI=1S/C10H18O/c1-9(2)7-4-5-10(9,3)8(11)6-7/h7-8,11H,4-6H2,1-3H3/t7-,8+,10+/m1/s1
iupac name: (1R,4R,6S)-1,7,7-trimethylbicyclo[2.2.1]heptan-6-ol
xref: CHEMBL486208
synonym: isoborneol
synonym: (+)-borneol
approved: f
ligand name: borneol
type: NaturalProductLigand

RU1968
in ch i key: OQLPSYJNZRYLOQ-VMQDKKENSA-N
in ch i: InChI=1S/C24H38N2O/c1-16(25-13-14-26(3)4)22-9-10-23-21-7-5-17-15-18(27)6-8-19(17)20(21)11-12-24(22,23)2/h6,8,15-16,20-23,25,27H,5,7,9-14H2,1-4H3/t16-,20+,21+,22+,23-,24+/m1/s1
comment: RU1968 is a cross-species inhibitor of CatSper Ca2+ channels <Reference id=37212/>. It can be used as a chemical probe to elucidate the function of CatSper channels in sperm from different species.
iupac name: (1R,3aR,3bR,9bR,11aR)-1-[(1R)-1-{[2-(dimethylamino)ethyl]amino}ethyl]-11a-methyl-1H,2H,3H,3aH,3bH,4H,5H,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-7-ol
approved: f
ligand name: RU1968
type: SyntheticOrganicLigand

GGsTop
canonical SMILES: COP(=O)(Oc1cccc(c1)CC(=O)O)CCC(C(=O)O)N
isomeric SMILES: COP(=O)(Oc1cccc(c1)CC(=O)O)CCC(C(=O)O)N
in ch i key: NTFPDEDRMYYPAC-UHFFFAOYSA-N
in ch i: InChI=1S/C13H18NO7P/c1-20-22(19,6-5-11(14)13(17)18)21-10-4-2-3-9(7-10)8-12(15)16/h2-4,7,11H,5-6,8,14H2,1H3,(H,15,16)(H,17,18)
comment: GGsTop is a nontoxic, and irreversible inhibitor of γ-glutamyltransferase (γ-glutamyl transpeptidase) <Reference id=37210/> (it is phosphonate diester 5a in this reference). The compound has two stereogenic centers and therefore has the potential to exist in 4 stereoisomeric forms <Reference id=37211/>. We show the structure without specified stereochemistry to represent the racemic mixture.
iupac name: 2-amino-4-[[3-(carboxymethyl)phenoxy]-methoxyphosphoryl]butanoic acid
xref: CHEMBL3948970
approved: f
ligand name: GGsTop
type: SyntheticOrganicLigand

MLS000536924
canonical SMILES: Cc1ccc(cc1)CSc1ncn(n1)c1ccccc1
isomeric SMILES: Cc1ccc(cc1)CSc1ncn(n1)c1ccccc1
in ch i key: JAVBFNWBMPZICK-UHFFFAOYSA-N
in ch i: InChI=1S/C16H15N3S/c1-13-7-9-14(10-8-13)11-20-16-17-12-19(18-16)15-5-3-2-4-6-15/h2-10,12H,11H2,1H3
comment: MLS000536924 is an inhibitor of human 15-lipoxygenase-2 (15-LOX-2) that was identified using high throughput screening <Reference id=37207/>.
iupac name: 3-[(4-methylphenyl)methylsulfanyl]-1-phenyl-1,2,4-triazole
xref: CHEMBL1452107
approved: f
ligand name: MLS000536924
type: SyntheticOrganicLigand

KV-37
isomeric SMILES: O=C(Nc1cc(/C=C/C(=O)O)ccc1CC=C(C)C)CCc1ccccc1
in ch i key: SMYHHZFAWOLAAX-RVDMUPIBSA-N
in ch i: InChI=1S/C23H25NO3/c1-17(2)8-12-20-13-9-19(11-15-23(26)27)16-21(20)24-22(25)14-10-18-6-4-3-5-7-18/h3-9,11,13,15-16H,10,12,14H2,1-2H3,(H,24,25)(H,26,27)/b15-11+
comment: KV-37 is as aldo-keto reductase 1C3 (AKR1C3) inhbitor <Reference id=37203/>. Its androgen biosynthesis-inhibiting activity has shown encouraging synergistic therapeutic potential in combination with <Ligand id=6812/> exposure in prostate cancer cells in vitro.
iupac name: (E)-3-[4-(3-methylbut-2-enyl)-3-(3-phenylpropanoylamino)phenyl]prop-2-enoic acid
approved: f
ligand name: KV-37
type: SyntheticOrganicLigand

AT-56
in ch i key: LQNGMDUIRLSESZ-UHFFFAOYSA-N
in ch i: InChI=1S/C25H27N5/c1-3-9-22-19(7-1)12-13-20-8-2-4-10-23(20)25(22)21-14-17-30(18-15-21)16-6-5-11-24-26-28-29-27-24/h1-4,7-10,12-13H,5-6,11,14-18H2,(H,26,27,28,29)
comment: AT-56 is an orally active, selective inhibitor of lipocalin-type prostaglandin D synthase (L-PGDS, PTGDS) <Reference id=37202/>.
iupac name: 1-[4-(2H-tetrazol-5-yl)butyl]-4-(2-tricyclo[9.4.0.03,8]pentadeca-1(15),3,5,7,9,11,13-heptaenylidene)piperidine
synonym: AT56
synonym: AT 56
approved: f
ligand name: AT-56
type: SyntheticOrganicLigand

methyprylon
canonical SMILES: CCC1(CC)C(=NCC(C1=O)C)O
isomeric SMILES: CCC1(CC)C(=NCC(C1=O)C)O
in ch i key: SIDLZWOQUZRBRU-UHFFFAOYSA-N
in ch i: InChI=1S/C10H17NO2/c1-4-10(5-2)8(12)7(3)6-11-9(10)13/h7H,4-6H2,1-3H3,(H,11,13)
comment: Methyprylon is a piperidinedione derivative sedative. It is not available in the UK or US.
iupac name: 5,5-diethyl-6-hydroxy-3-methyl-2,3,4,5-tetrahydropyridin-4-one
xref: CHEMBL1200790
synonym: Noludar®
approved: t
ligand name: methyprylon
type: SyntheticOrganicLigand

SPP1
in ch i key: ZZZVRFJGTJAHFM-UHFFFAOYSA-N
in ch i: InChI=1S/C24H34N4O3/c1-18-4-3-5-20(16-18)28-17-25(2)22(29)24(28)10-14-26(15-11-24)19-8-12-27(13-9-19)23(30)31-21-6-7-21/h3-5,16,19,21H,6-15,17H2,1-2H3
comment: Functionally selective, brain penetrant partial orthosteric agonist at M1 receptors <Reference id=37190/>.
iupac name: cyclopropyl 4-[3-methyl-1-(3-methylphenyl)-4-oxo-1,3,8-triazaspiro[4.5]decan-8-yl]piperidine-1-carboxylate
synonym: spiropiperidine 1
approved: f
ligand name: SPP1
type: SyntheticOrganicLigand

compound 1u [PMID: 30245402]
in ch i key: HZYLVYNCWLAIGF-UHFFFAOYSA-N
in ch i: InChI=1S/C26H33N3O4/c1-18(2)20-12-14-22(15-13-20)26(32)29(17-24(30)27-23-6-4-3-5-7-23)16-19-8-10-21(11-9-19)25(31)28-33/h8-15,18,23,33H,3-7,16-17H2,1-2H3,(H,27,30)(H,28,31)
comment: Compound 1u is the hit compound identified from a SAR study of peptoid-based histone deacetylase (HDAC) inhibitors for use as antimalarial agents <Reference id=37187/>. The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
iupac name: 4-[[[2-(cyclohexylamino)-2-oxoethyl]-(4-propan-2-ylbenzoyl)amino]methyl]-N-hydroxybenzamide
approved: f
ligand name: compound 1u [PMID: 30245402]
type: SyntheticOrganicLigand

GR-389988
in ch i key: HVRWZFQFSQUILC-UHFFFAOYSA-N
in ch i: InChI=1S/C26H26N6O3/c1-31-15-20(13-29-31)19-11-22-25(28-12-19)32(26(27)30-22)14-18-6-9-23(24(10-18)34-3)35-16-17-4-7-21(33-2)8-5-17/h4-13,15H,14,16H2,1-3H3,(H2,27,30)
comment: GR-389988 (a.k.a. GZ389988) is a neurotrophic receptor tyrosine kinase/Trk inhibitor that was developed by Genzyme. It blocks nerve growth factor (NGF)/Trk pathway activation. The chemical structure is claimed in Genzyme's patent US9174986B2 for utility in the treatment of inflammatory diseases, autoimmune disease, defects of bone metabolism and/or cancer, and especially for the management of osteoarthritis and osteoarthritis pain. GR-389988 also inhibits c-FMS, the cellular receptor for colony stimulating factor-1 (CSF-1).
xref: CHEMBL3673452
synonym: GR389988
synonym: GZ389988
synonym: Ex. 3-15 [US9174986B2]
synonym: GZ389988A
approved: f
ligand name: GR-389988
type: SyntheticOrganicLigand

cinromide
canonical SMILES: CCNC(=O)C=Cc1cccc(c1)Br
isomeric SMILES: CCNC(=O)/C=C/c1cccc(c1)Br
in ch i key: LDCXGZCEMNMWIL-VOTSOKGWSA-N
in ch i: InChI=1S/C11H12BrNO/c1-2-13-11(14)7-6-9-4-3-5-10(12)8-9/h3-8H,2H2,1H3,(H,13,14)/b7-6+
comment: Cinromide exhibited antiepileptic (anticonvulsant) activity in animal models but very limited clinical usefulness in humans.
iupac name: (2E)-3-(3-bromophenyl)-N-ethylprop-2-enamide
xref: CHEMBL93233
synonym: 3-bromo-N-ethylcinnamamide
approved: f
ligand name: cinromide
type: SyntheticOrganicLigand

DO264
in ch i key: PIEQDBPBBQPLPL-UHFFFAOYSA-N
comment: DO264 is a selective inhibitor of the serine hydrolase, ABHD12 <Reference id=37086/><Reference id=37079/>. It produces immunostimulatory effects in vitro and in vivo, and is suitable as a tool compound to investigate the biological functions of ABHD12 <Reference id=37087/><Reference id=37088/>.
iupac name: 1-[1-[3-chloro-4-[2-chloro-4-(trifluoromethoxy)phenoxy]pyridin-2-yl]piperidin-4-yl]-3-pyridin-3-ylthiourea
synonym: DO-264
synonym: compound 46
approved: f
ligand name: DO264
type: SyntheticOrganicLigand

Jedi1
canonical SMILES: OC(=O)c1cc(oc1C)c1ccccc1
isomeric SMILES: OC(=O)c1cc(oc1C)c1ccccc1
in ch i key: VLMNACSEESRUAK-UHFFFAOYSA-N
in ch i: InChI=1S/C12H10O3/c1-8-10(12(13)14)7-11(15-8)9-5-3-2-4-6-9/h2-7H,1H3,(H,13,14)
comment: Piezo1 chemical activator.
iupac name: 2-methyl-5-phenylfuran-3-carboxylic acid
approved: f
ligand name: Jedi1
type: SyntheticOrganicLigand

ASP8477
canonical SMILES: O=C(C1CCN(CC1)C(=O)Oc1cccnc1)Nc1ccccc1
isomeric SMILES: O=C(C1CCN(CC1)C(=O)Oc1cccnc1)Nc1ccccc1
in ch i key: PLCMZPFTMOAGOE-UHFFFAOYSA-N
in ch i: InChI=1S/C18H19N3O3/c22-17(20-15-5-2-1-3-6-15)14-8-11-21(12-9-14)18(23)24-16-7-4-10-19-13-16/h1-7,10,13-14H,8-9,11-12H2,(H,20,22)
comment: ASP8477 is a small molecule, orally active inhibitor of the fatty acid amide hydrolase enzymes FAAH and FAAH-2, that is active in vitro and in vivo <Reference id=37069/>. Experimental evidence indicates that it produces CNS-driven analgesia.
iupac name: pyridin-3-yl 4-(phenylcarbamoyl)piperidine-1-carboxylate
approved: f
ligand name: ASP8477
type: SyntheticOrganicLigand

cladosporin
canonical SMILES: CC1CCCC(O1)CC1OC(=O)c2c(C1)cc(cc2O)O
in ch i key: WOMKDMUZNBFXKG-ZWKOPEQDSA-N
in ch i: InChI=1S/C16H20O5/c1-9-3-2-4-12(20-9)8-13-6-10-5-11(17)7-14(18)15(10)16(19)21-13/h5,7,9,12-13,17-18H,2-4,6,8H2,1H3/t9-,12+,13+/m0/s1
comment: Cladosporin is a tricyclic octaketide that is a secondary metabolite produced by several fungal genera including Cladosporium and Aspergillus. Cladosporin exhibits broad-spectrum bioactivity, including antimalarial, antifungal, antibacterial, plant growth inhibitory properties and mammalian anti-inflammatory effects. The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
iupac name: (3R)-3-[[(2R,6S)-6-methyloxan-2-yl]methyl]-6,8-bis(oxidanyl)-3,4-dihydroisochromen-1-one
xref: CHEMBL448685
synonym: asperentin
approved: f
ligand name: cladosporin
type: NaturalProductLigand

LEI105
in ch i key: XDHONXIOZAUYDB-UHFFFAOYSA-N
in ch i: InChI=1S/C25H24N2O2/c1-18-12-14-20(15-13-18)21-16-23-24(26-17-21)27-25(29-23)22(28)11-7-3-6-10-19-8-4-2-5-9-19/h2,4-5,8-9,12-17H,3,6-7,10-11H2,1H3
comment: LEI105 is a diacylglycerol lipase (DAGL) inhibitor <Reference id=37054/>.
iupac name: 1-[6-(4-methylphenyl)-[1,3]oxazolo[4,5-b]pyridin-2-yl]-6-phenylhexan-1-one
synonym: LEI-105
approved: f
ligand name: LEI105
type: SyntheticOrganicLigand

KT-109
in ch i key: JKJMWHULJIOKPJ-UHFFFAOYSA-N
in ch i: InChI=1S/C27H26N4O/c32-27(30-18-8-7-13-25(30)19-21-9-3-1-4-10-21)31-20-26(28-29-31)24-16-14-23(15-17-24)22-11-5-2-6-12-22/h1-6,9-12,14-17,20,25H,7-8,13,18-19H2
comment: KT-109 is a diacylglycerol lipase inhibitor <Reference id=37053/>.
xref: CHEMBL2144065
synonym: KT109
approved: f
ligand name: KT-109
type: SyntheticOrganicLigand

diclofenamide
canonical SMILES: Clc1cc(cc(c1Cl)S(=O)(=O)N)S(=O)(=O)N
isomeric SMILES: Clc1cc(cc(c1Cl)S(=O)(=O)N)S(=O)(=O)N
in ch i key: GJQPMPFPNINLKP-UHFFFAOYSA-N
comment: Dichlorphenamide is an oral carbonic anhydrase inhibitor.
iupac name: 4,5-dichlorobenzene-1,3-disulfonamide
xref: CHEMBL17
synonym: Keveyis®
synonym: Antidrasi
synonym: Glaucol
synonym: Oratrol
synonym: Dasanide
synonym: Daranide®
synonym: dichlofenamide
synonym: glauconide
synonym: dichlorphenamide
approved: t
ligand name: diclofenamide
type: SyntheticOrganicLigand

DH376
in ch i key: GVLOFRPVRYAFKI-VSGBNLITSA-N
in ch i: InChI=1S/C31H28F2N4O3/c1-2-18-40-28-17-16-27(19-22-6-4-3-5-7-22)36(21-28)30(38)37-34-20-29(35-37)31(39,23-8-12-25(32)13-9-23)24-10-14-26(33)15-11-24/h1,3-15,20,27-28,39H,16-19,21H2/t27-,28-/m1/s1
comment: DH376 is a diacylglycerol lipase inhibitor <Reference id=37051/>.
iupac name: {2-[(2R,5R)-2-benzyl-5-(but-3-yn-1-yl)piperidine-1-carbonyl]-2H-1,2,3-triazol-4-yl}bis(4-fluorophenyl)methanol
xref: CHEMBL3895863
synonym: DH-376
synonym: inhibitor 38
approved: f
ligand name: DH376
type: SyntheticOrganicLigand

DO34
in ch i key: CQGMWUWJVBKTRM-UHFFFAOYSA-N
in ch i: InChI=1S/C26H28F3N5O4/c1-25(2,3)38-24(36)32-13-14-33(20(16-32)15-18-7-5-4-6-8-18)23(35)34-17-22(30-31-34)19-9-11-21(12-10-19)37-26(27,28)29/h4-12,17,20H,13-16H2,1-3H3
comment: DO34 is a diacylglycerol lipase inhibitor <Reference id=37051/><Reference id=37052/>.
iupac name: tert-butyl 3-benzyl-4-{4-[4-(trifluoromethoxy)phenyl]-1H-1,2,3-triazole-1-carbonyl}piperazine-1-carboxylate
synonym: DO-34
approved: f
ligand name: DO34
type: SyntheticOrganicLigand

SC-236
in ch i key: NSQNZEUFHPTJME-UHFFFAOYSA-N
comment: SC-236 is a selective COX-2 inhibitor <Reference id=37050/>. It was an early structural lead that lead to the development of <Ligand id=2892/>.
iupac name: 4-[5-(4-chlorophenyl)-3-(trifluoromethyl)pyrazol-1-yl]benzenesulfonamide
xref: CHEMBL282093
synonym: SC236
synonym: compound 1f [PMID: 9135032]
approved: f
ligand name: SC-236
type: SyntheticOrganicLigand

VU0155094
in ch i key: BCNKQXDDMIBITO-UHFFFAOYSA-N
in ch i: InChI=1S/C24H24N2O4S/c1-15-13-22(16(2)26(15)20-9-5-18(6-10-20)24(29)30-4)23(28)14-31-21-11-7-19(8-12-21)25-17(3)27/h5-13H,14H2,1-4H3,(H,25,27)
comment: VU0155094 is a potent, selective pan-Group III mGlu positive allosteric modulator.
iupac name: methyl 4-[3-[2-(4-acetamidophenyl)sulfanylacetyl]-2,5-dimethylpyrrol-1-yl]benzoate
synonym: VU-0155094
synonym: VU 0155094
synonym: ML397
synonym: ML-397
synonym: ML 397
approved: f
ligand name: VU0155094
type: SyntheticOrganicLigand

VU0650786
in ch i key: RXRVCJFGSOVYLG-LLVKDONJSA-N
comment: mGlu3 receptor negative allosteric modulator.
iupac name: (7R)-2-{[(5-chloropyridin-2-yl)oxy]methyl}-5-(2-fluoropyridin-3-yl)-7-methyl-4H,5H,6H,7H-pyrazolo[1,5-a]pyrazin-4-one
synonym: VU-0650786
synonym: VU 0650786
approved: f
ligand name: VU0650786
type: SyntheticOrganicLigand

NE 52-QQ57
in ch i key: HXPQWNPLNIEJOW-UHFFFAOYSA-N
in ch i: InChI=1S/C24H28N6O/c1-4-21-20(22-26-15(2)13-16(3)30(22)29-21)14-17-5-7-18(8-6-17)23-27-28-24(31-23)19-9-11-25-12-10-19/h5-8,13,19,25H,4,9-12,14H2,1-3H3
comment: NE 52-QQ57 is an orally bioavailable, selective antagonist of the class A orphan GPCR, GPR4 <Reference id=36806/>. It is one of the chemical structures claimed in Novartis' patent WO2012131633A1 <Reference id=36807/>.
iupac name: 2-[4-[(2-ethyl-5,7-dimethylpyrazolo[1,5-a]pyrimidin-3-yl)methyl]phenyl]-5-piperidin-4-yl-1,3,4-oxadiazole
xref: CHEMBL3675743
synonym: NE52-QQ57
synonym: GPR4 antagonist 13
synonym: example 35 [WO2012131633A1]
approved: f
ligand name: NE 52-QQ57
type: SyntheticOrganicLigand

MRS7469
in ch i key: KATPAPFGRPJUHJ-MXKWNSRKSA-N
in ch i: InChI=1S/C21H28ClN5O3/c22-20-25-18(24-13(10-3-1-4-10)11-5-2-6-11)14-19(26-20)27(9-23-14)15-12-7-21(12,8-28)17(30)16(15)29/h9-13,15-17,28-30H,1-8H2,(H,24,25,26)/t12-,15-,16+,17+,21+/m1/s1
comment: Selective A1 receptor agonist.
iupac name: (1R,2R,3S,4R,5S)-4-{2-chloro-6-[(dicyclobutylmethyl)amino]-9H-purin-9-yl}-1-(hydroxymethyl)bicyclo[3.1.0]hexane-2,3-diol
approved: f
ligand name: MRS7469
type: SyntheticOrganicLigand

compound 22 [PMID: 24754609]
in ch i key: VYPWROGLWNYKDD-UHFFFAOYSA-N
in ch i: InChI=1S/C22H24N6O2S/c1-3-8-28-13-17(25-14-28)6-7-24-21(29)27-22-26-19-5-4-15(10-20(19)31-22)16-9-18(30-2)12-23-11-16/h4-5,9-14H,3,6-8H2,1-2H3,(H2,24,26,27,29)
comment: Compound 22 is an isoform-selective PI3Kγ inhibitor <Reference id=36986/><Reference id=36987/>.
iupac name: 1-[6-(5-methoxypyridin-3-yl)-1,3-benzothiazol-2-yl]-3-[2-(1-propylimidazol-4-yl)ethyl]urea
xref: CHEMBL3356900
approved: f
ligand name: compound 22 [PMID: 24754609]
type: SyntheticOrganicLigand

AZ2
in ch i key: CNCRCDLWUGCPSJ-LBPRGKRZSA-N
in ch i: InChI=1S/C20H23N3O2S/c1-10-7-15(18-11(2)21-20(26-18)22-13(4)24)8-16-9-23(19(25)17(10)16)12(3)14-5-6-14/h7-8,12,14H,5-6,9H2,1-4H3,(H,21,22,24)/t12-/m0/s1
comment: AZ2 is a highly selective inhibitor of the lipid kinase PI3Kγ <Reference id=36980/>. It represents a novel chemotype that binds to a conserved part of the ATP-binding pocket (Type I inhibitor-like), but once bound the inhibitor induces a DFG-out (active state) conformational change and rearrangement of the activation loop (analogous to Type II protein kinase inhibitors). This mechanism occurs only in PI3Kγ. Analogues of this novel class of PI3Kγ inhibitors, with enhanced pharmacokinetic properties and in vivo potency (e.g. <Ligand id=9997/>), have been reported <Reference id=35279/>.
iupac name: N-(5-{2-[(1S)-1-cyclopropylethyl]-7-methyl-1-oxo-2,3-dihydro-1H-isoindol-5-yl}-4-methyl-1,3-thiazol-2-yl)acetamide
approved: f
ligand name: AZ2
type: SyntheticOrganicLigand

SUVN-G3031
in ch i key: LNXDUSQEXVQFGP-UHFFFAOYSA-N
in ch i: InChI=1S/C21H31N3O3/c25-21(16-23-12-14-26-15-13-23)22-17-4-6-19(7-5-17)27-20-8-10-24(11-9-20)18-2-1-3-18/h4-7,18,20H,1-3,8-16H2,(H,22,25)
comment: SUVN-G3031 is a potent, orally active histamine H3 receptor inverse agonist, that has demonstrated wake-promoting activity in a rat sleep disorder model <Reference id=36978/>. It was synthesised as the dihydrochloride (PubChem CID 60151476). We present the parent molecule here.
iupac name: N-[4-(1-cyclobutyl-piperidin-4-yloxy)phenyl]-2-(morpholin-4-yl)acetamide
approved: f
ligand name: SUVN-G3031
type: SyntheticOrganicLigand

vecabrutinib
in ch i key: QLRRJMOBVVGXEJ-XHSDSOJGSA-N
comment: Vecabrutinib (SNS-062) is a second generation, noncovalent (reversible) Bruton's tyrosine kinase (BTK) inhibitor that is being developed by Sunesis Pharmaceuticals as a therapeutic for B cell malignancies that have developed resistance to first generation BTK inhibitors such as <Ligand id=6912/>, through acquisition of the Cys481Ser mutation in the enzyme's active site. The structure presented here was obtained by searching PubChem using the IUPAC structure that was submitted to the WHO for the INN vecabrutinib. Sunesis' website associates the INN with the research code SNS-062 <Reference id=36950/>. Formal name-to-structure identification and pharmacological analysis are yet to be disclosed in a peer-reviewed publication. Patent interrogation identifies example I-1 in Biogen/Sunesis' patent WO2013185084A1 as a structure match to vecabrutinib <Reference id=36955/>.
iupac name: (3R,3'R,4'S)-1'-(6-amino-5-fluoropyrimidin-4-yl)-3-[3-chloro-5-(trifluoromethyl)anilino]-2-oxo[1,3'-bipiperidine]-4'-carboxamide
synonym: SNS-062
synonym: SNS062
synonym: BIIB-062
synonym: BIIB062
approved: f
ligand name: vecabrutinib
type: SyntheticOrganicLigand

AS2717638
in ch i key: QRMYHYZQUGJBBX-UHFFFAOYSA-N
in ch i: InChI=1S/C25H25N3O5/c1-15-7-8-20-18(11-15)23(26-33-20)28-14-19(24(29)27-9-5-4-6-10-27)16-12-21(31-2)22(32-3)13-17(16)25(28)30/h7-8,11-14H,4-6,9-10H2,1-3H3
comment: AS2717638 is a lysophosphatidic acid receptor 5 (LPA5) antagonist <Reference id=36943/>. It is selective for LPA5 over other LPA receptors tested in ligand binding assays.
iupac name: 6,7-dimethoxy-2-(5-methyl-1,2-benzoxazol-3-yl)-4-(piperidin-1-ylcarbonyl)isoquinolin-1(2H)-one
approved: f
ligand name: AS2717638
type: SyntheticOrganicLigand

MMV008138
in ch i key: ZJDRIKAAFJMYGX-UHFFFAOYSA-N
comment: MMV008138 is a drug-like compound with antimalarial activity that was chosen as one of the chemotypes to be included in the MMV Malaria Box <Reference id=38140/><Reference id=37908/>. The 1R,3S enantiomer, represented by PubChem CID 987146, has the highest antimalarial potency <Reference id=37055/><Reference id=37059/>. The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
iupac name: 1-(2,4-dichlorophenyl)-2,3,4,9-tetrahydro-1H-pyrido[5,4-b]indole-3-carboxylic acid
xref: CHEMBL527593
synonym: TCMDC-125815
synonym: GNF-Pf-4188
synonym: MMV-08138
approved: f
ligand name: MMV008138
type: SyntheticOrganicLigand

SLC4101431
in ch i key: PDCYPMBTPMGZDZ-DEOSSOPVSA-N
in ch i: InChI=1S/C29H27N7OS/c30-28(31)36-16-4-7-24(36)17-26-34-27(35-37-26)22-12-14-23(15-13-22)32-29-33-25(18-38-29)21-10-8-20(9-11-21)19-5-2-1-3-6-19/h1-3,5-6,8-15,18,24H,4,7,16-17H2,(H3,30,31)(H,32,33)/t24-/m0/s1
comment: SLC4101431 is a sphihgosine kinase inhibitor with ~100-fold selectivity for the SK2 isozyme compared to SK1 <Reference id=36878/>.
iupac name: (S)-(2-((3-(4-((4-([1,1′-Biphenyl]-4-yl)thiazol-2-yl)amino)phenyl)-1,2,4-oxadiazol-5-yl)methyl)pyrrolidin-1-yl) (amino)methaniminium
synonym: compound 20dd [PMID: 28406646]
approved: f
ligand name: SLC4101431
type: SyntheticOrganicLigand

oryzatensin
in ch i key: CUWIGJUCRMYFBS-BXXNOCLASA-N
comment: Oryzatensin is a complement receptor C3a peptide agonist that was isolated from a tryptic digest of rice albumin <Reference id=36932/>.
iupac name: glycyl-L-tyrosyl-L-prolyl-L-methionyl-L-tyrosyl-L-prolyl-L-leucyl-L-prolyl-L-arginine
approved: f
ligand name: oryzatensin
type: PeptideLigand

albutensin A
in ch i key: CWUCHJAUTZCVMY-YUIUFFEESA-N
in ch i: InChI=1S/C46H76N14O11/c1-23(2)19-33(57-37(62)25(5)48)41(66)55-31(15-10-11-17-47)40(65)53-26(6)39(64)58-34(20-28-21-52-30-14-9-8-13-29(28)30)42(67)59-35(22-61)43(68)60-36(24(3)4)44(69)54-27(7)38(63)56-32(45(70)71)16-12-18-51-46(49)50/h8-9,13-14,21,23-27,31-36,52,61H,10-12,15-20,22,47-48H2,1-7H3,(H,53,65)(H,54,69)(H,55,66)(H,56,63)(H,57,62)(H,58,64)(H,59,67)(H,60,68)(H,70,71)(H4,49,50,51)/t25-,26-,27-,31-,32-,33-,34-,35-,36-/m0/s1
comment: Albutensin A is a serum albumin-derived peptide <Reference id=36930/>. It acts as an agonist of the complement C3a and C5a receptors <Reference id=36931/>.
iupac name: L-alanyl-L-leucyl-L-lysyl-L-alanyl-L-tryptophyl-L-seryl-L-valyl-L-alanyl-L-arginine
approved: f
ligand name: albutensin A
type: PeptideLigand

AN3661
canonical SMILES: OC(=O)CCc1cccc2c1B(O)OC2
isomeric SMILES: OC(=O)CCc1cccc2c1B(O)OC2
in ch i key: CEVOKIPNIZQANN-UHFFFAOYSA-N
in ch i: InChI=1S/C10H11BO4/c12-9(13)5-4-7-2-1-3-8-6-15-11(14)10(7)8/h1-3,14H,4-6H2,(H,12,13)
comment: AN3661 is a compound with potent antimalarial activity and belongs to a novel class of boron-containing compounds, the benzoxaboroles <Reference id=37456/>. The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
iupac name: 3-(1-hydroxy-3H-2,1-benzoxaborol-7-yl)propanoic acid
xref: CHEMBL1643740
approved: f
ligand name: AN3661
type: SyntheticOrganicLigand

ML10
in ch i key: VRZZXBIIWWZFEI-UHFFFAOYSA-N
in ch i: InChI=1S/C26H29FN6O2S/c1-16-14-33-24(13-19(16)15-32(2)3)30-25(18-7-8-20(27)22(12-18)31-36(4,34)35)26(33)21-9-10-28-23(29-21)11-17-5-6-17/h7-10,12-14,17,31H,5-6,11,15H2,1-4H3
comment: ML10 is the lead compound from an imidazopyridine series with antimalarial activity <Reference id=36793/>. The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
iupac name: N-[5-[3-[2-(cyclopropylmethyl)pyrimidin-4-yl]-7-[(dimethylamino)methyl]-6-methylimidazo[1,2-a]pyridin-2-yl]-2-fluorophenyl]methanesulfonamide
approved: f
ligand name: ML10
type: SyntheticOrganicLigand

norendoxifen
isomeric SMILES: NCCOc1ccc(cc1)/C(=C(/c1ccccc1)/CC)/c1ccc(cc1)O
in ch i key: YCQBLTPGQSYLHD-VHXPQNKSSA-N
in ch i: InChI=1S/C24H25NO2/c1-2-23(18-6-4-3-5-7-18)24(19-8-12-21(26)13-9-19)20-10-14-22(15-11-20)27-17-16-25/h3-15,26H,2,16-17,25H2,1H3/b24-23-
comment: Norendoxifen is an active metabolite of tamoxifen. In addition to acting as an estrogen receptor modulator, norendoxifen also inhibits aromatase enzyme activity (i.e. inhibits estrogen biosynthesis) <Reference id=36773/><Reference id=36774/>. We show the Z isomer here as it is more potent in terms of ER modulation and in vivo activity compared to the E isomer.
iupac name: 4-[(~{Z})-1-[4-(2-aminoethoxy)phenyl]-2-phenylbut-1-enyl]phenol
xref: CHEMBL2386284
synonym: Z-norendoxifen
approved: f
ligand name: norendoxifen
type: SyntheticOrganicLigand

casoxin C
in ch i key: FLMZYYASMMUDFC-FJKDSYQFSA-N
in ch i: InChI=1S/C60H94N14O15/c1-9-33(7)48(72-55(84)45-14-12-26-74(45)58(87)49(34(8)10-2)73-50(79)39(61)28-35-15-19-37(76)20-16-35)57(86)66-40(23-24-46(62)78)51(80)68-43(29-36-17-21-38(77)22-18-36)53(82)71-47(32(5)6)56(85)69-42(27-31(3)4)52(81)70-44(30-75)54(83)67-41(59(88)89)13-11-25-65-60(63)64/h15-22,31-34,39-45,47-49,75-77H,9-14,23-30,61H2,1-8H3,(H2,62,78)(H,66,86)(H,67,83)(H,68,80)(H,69,85)(H,70,81)(H,71,82)(H,72,84)(H,73,79)(H,88,89)(H4,63,64,65)/t33-,34-,39-,40-,41-,42-,43-,44-,45-,47-,48-,49-/m0/s1
comment: Casoxin C is a bioactive peptide derived from a tryptic digest of bovine κ-casein <Reference id=36929/>. It shares sequence homology with complement peptide C3a(70-77) and acts as an agonist of the C3a complement peptide receptor.
iupac name: L-tyrosyl-L-isoleucyl-L-prolyl-L-isoleucyl-L-glutaminyl-L-tyrosyl-L-valyl-L-leucyl-L-seryl-L-arginine
approved: f
ligand name: casoxin C
type: PeptideLigand

TAK-448
in ch i key: MWXWMWSUUYXMRA-GRKBUMBKSA-N
in ch i: InChI=1S/C58H80N16O14/c1-30(2)22-42(51(82)66-40(16-11-21-63-57(61)62-5)50(81)67-41(49(60)80)25-35-28-64-39-15-10-9-14-38(35)39)70-58(88)73-72-53(84)43(23-33-12-7-6-8-13-33)69-55(86)48(31(3)75)71-52(83)44(27-47(59)79)68-54(85)46-26-37(78)29-74(46)56(87)45(65-32(4)76)24-34-17-19-36(77)20-18-34/h6-10,12-15,17-20,28,30-31,37,40-46,48,64,75,77-78H,11,16,21-27,29H2,1-5H3,(H2,59,79)(H2,60,80)(H,65,76)(H,66,82)(H,67,81)(H,68,85)(H,69,86)(H,71,83)(H,72,84)(H3,61,62,63)(H2,70,73,88)/t31-,37-,40+,41+,42+,43+,44+,45-,46+,48+/m1/s1
comment: TAK-448 is a nine amino acid kisspeptin receptor agonist <Reference id=36913/>. It has good water solubility.
synonym: analogue 24 [PMID: 27589480]
synonym: TAK448
synonym: RVT-602
approved: f
ligand name: TAK-448
type: PeptideLigand

fisogatinib
in ch i key: MGZKYOAQVGSSGC-DLBZAZTESA-N
comment: Fisogatinib (BLU-554) is an orally bioavailable, potent and highly selective fibroblast growth factor receptor 4 (FGFR4) inhibitor. It was discovered by Blueprint Medicines <Reference id=36887/> (probably compound number 40 therein), and is being investigated for clinical anti-tumour efficacy in cancers that are driven by FGFR4 activation (for example, in liver cancers where the FGF19/FGFR4 signalling pathway is activated by genetic alteration). Structurally, fisogatinib is a derivative of <Ligand id=8862/> and is similarly an irreversible type tryosine kinase inhibitor.
iupac name: N-((3S,4S)-3-((6-(2,6-dichloro-3,5-dimethoxyphenyl)quinazolin-2-yl)amino)tetrahydro-2H-pyran-4-yl)acrylamide
synonym: BLU-554
synonym: BLU554
synonym: CS3008
synonym: CS-3008
approved: f
ligand name: fisogatinib
type: SyntheticOrganicLigand

MP-A08
isomeric SMILES: Cc1ccc(cc1)S(=O)(=O)Nc1ccccc1/N=C/c1ccccc1NS(=O)(=O)c1ccc(cc1)C
in ch i key: FLDBNMYJUMAXDQ-TURZUDJPSA-N
in ch i: InChI=1S/C27H25N3O4S2/c1-20-11-15-23(16-12-20)35(31,32)29-25-8-4-3-7-22(25)19-28-26-9-5-6-10-27(26)30-36(33,34)24-17-13-21(2)14-18-24/h3-19,29-30H,1-2H3/b28-19+
comment: MP-A08 is a inhibitor of sphongosine kinases 1 and 2 <Reference id=36885/>. It is selective for these two enzymes over a panel of other kinases. Notably this is an ATP-competitive inhibitor rather than a sphingosine-competitive compound.
xref: CHEMBL3764617
approved: f
ligand name: MP-A08
type: SyntheticOrganicLigand

compound 27d [PMID: 28231433]
in ch i key: OHVIRCSJFFPEGC-XMMPIXPASA-N
in ch i: InChI=1S/C26H28N2O3/c29-18-24-9-5-15-28(24)17-20-11-13-21(14-12-20)19-31-25-10-4-8-23(16-25)27-26(30)22-6-2-1-3-7-22/h1-4,6-8,10-14,16,24,29H,5,9,15,17-19H2,(H,27,30)/t24-/m1/s1
comment: Compound 27d is a sphingosine kinase inhibitor with selectivity for the SK2 isozyme <Reference id=36874/>.
iupac name: (R)-N-(3-((4-((2-(Hydroxymethyl)pyrrolidin-1-yl)methyl)benzyl)oxy)phenyl)benzamide
approved: f
ligand name: compound 27d [PMID: 28231433]
type: SyntheticOrganicLigand

KH7
isomeric SMILES: Brc1ccc(c(c1)/C=N/NC(=O)C(Sc1nc2c([nH]1)cccc2)C)O
in ch i key: WILMXUAKQKGGCC-DJKKODMXSA-N
comment: KH7 is a soluble adenylyl cyclase inhibitor <Reference id=22112/>.
synonym: KH 7
synonym: KH-7
approved: f
ligand name: KH7
type: SyntheticOrganicLigand

FD6
in ch i key: MTINGHUODSDGHI-JDHRZFKJSA-N
in ch i: InChI=1S/C27H48N2O7/c1-10-24(5)15-19(32)27(33)25(6)18(31)11-12-23(3,4)21(25)20(34-16-28-13-14-29(8)9)22(35-17(2)30)26(27,7)36-24/h18,20-22,28,31,33H,10-16H2,1-9H3/t18-,20-,21-,22-,24-,25-,26+,27-/m0/s1
comment: FD6 is a <Ligand id=5190/> derivative <Reference id=17845/>.
iupac name: (3S,4aR,5S,6S,6aS,10S,10aR,10bS)-6-({[2-(dimethylamino)ethyl]amino}methoxy)-3-ethyl-10,10b-dihydroxy-3,4a,7,7,10a-pentamethyl-1-oxo-dodecahydro-1H-naphtho[2,1-b]pyran-5-yl acetate
synonym: 6-[3-(dimethylamino)propionyl]-14 15-dihydroforskolin
approved: f
ligand name: FD6
type: SyntheticOrganicLigand

FD1
in ch i key: RWDRIGNPXMZENV-CLFUUGQNSA-N
in ch i: InChI=1S/C26H40N2O7S/c1-8-23(5)13-18(31)26(32)24(6)17(30)9-10-22(3,4)20(24)19(33-14-27-11-12-28-15-36)21(34-16(2)29)25(26,7)35-23/h8,17,19-21,27,30,32H,1,9-14H2,2-7H3/t17-,19-,20-,21-,23-,24-,25+,26-/m0/s1
comment: FD1 is a <Ligand id=5190/> derivative <Reference id=17845/>.
iupac name: (3R,4aR,5S,6S,6aS,10S,10aR,10bS)-3-ethenyl-10,10b-dihydroxy-6-{[(2-isothiocyanatoethyl)amino]methoxy}-3,4a,7,7,10a-pentamethyl-1-oxo-dodecahydro-1H-naphtho[2,1-b]pyran-5-yl acetate
synonym: 6-[N-(2-isothiocyanatoethyl) aminocarbonyl]forskolin
approved: f
ligand name: FD1
type: SyntheticOrganicLigand

olinciguat
in ch i key: YWQFJNWMWZMXRW-HXUWFJFHSA-N
in ch i: InChI=1S/C21H16F5N7O3/c22-12-4-2-1-3-11(12)9-33-16(14-5-6-36-32-14)7-15(31-33)18-28-8-13(23)17(30-18)29-10-20(35,19(27)34)21(24,25)26/h1-8,35H,9-10H2,(H2,27,34)(H,28,29,30)/t20-/m1/s1
comment: olinciguat (IW-1701) is an orally bioavailable stimulator of (NO)-sensitive soluble guanylyl cyclase (sGC) <Reference id=36851/> that is being developed by Ironwood Pharmaceuticals as a potential sickle cell disease therapeutic <Reference id=36850/>. It acts as a cGMP amplifying agent.
iupac name: (2~{R})-3,3,3-trifluoro-2-[[[5-fluoro-2-[1-[(2-fluorophenyl)methyl]-5-(1,2-oxazol-3-yl)pyrazol-3-yl]pyrimidin-4-yl]amino]methyl]-2-hydroxypropanamide
synonym: IW-1701
synonym: IW1701
approved: f
ligand name: olinciguat
type: SyntheticOrganicLigand

noscapine
in ch i key: AKNNEGZIBPJZJG-MSOLQXFVSA-N
in ch i: InChI=1S/C22H23NO7/c1-23-8-7-11-9-14-20(29-10-28-14)21(27-4)15(11)17(23)18-12-5-6-13(25-2)19(26-3)16(12)22(24)30-18/h5-6,9,17-18H,7-8,10H2,1-4H3/t17-,18+/m1/s1
comment: Noscapine is an alkaloid derived from the opium poppy Papaver somniferum, that has mild analgesic, antitussive, and potential antineoplastic activities.
iupac name: (3S)-6,7-dimethoxy-3-[(5R)-4-methoxy-6-methyl-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-3H-2-benzofuran-1-one
approved: f
ligand name: noscapine
type: NaturalProductLigand

GPR4 antagonist 3b
in ch i key: YFBWGDXTUXTMEM-UHFFFAOYSA-N
in ch i: InChI=1S/C31H37N5/c1-4-29-34-30-21(2)16-22(3)32-31(30)36(29)20-24-9-13-28-26(18-24)11-10-25-17-23(8-12-27(25)33-28)19-35-14-6-5-7-15-35/h8-9,12-13,16-18,33H,4-7,10-11,14-15,19-20H2,1-3H3
comment: Compound 3b is reported as a selective antagonist of the acid-sensing GPCR, GPR4 <Reference id=36814/>. It is a suitable pharmacological tool for in vtro and in vivo study of GPR4's role in tissue acidosis and consequential pathological tissue damage.
iupac name: 3-[(2-ethyl-5,7-dimethylimidazo[4,5-b]pyridin-3-yl)methyl]-8-(piperidin-1-ylmethyl)-6,11-dihydro-5~{H}-benzo[b][1]benzazepine
xref: CHEMBL3810385
synonym: compound 3b [PMID: 27190599]
approved: f
ligand name: GPR4 antagonist 3b
type: SyntheticOrganicLigand

endoxifen
isomeric SMILES: CNCCOc1ccc(cc1)/C(=C(/c1ccccc1)/CC)/c1ccc(cc1)O
in ch i key: MHJBZVSGOZTKRH-IZHYLOQSSA-N
in ch i: InChI=1S/C25H27NO2/c1-3-24(19-7-5-4-6-8-19)25(20-9-13-22(27)14-10-20)21-11-15-23(16-12-21)28-18-17-26-2/h4-16,26-27H,3,17-18H2,1-2H3/b25-24-
comment: Endoxifen is the most active metabolite of tamoxifen. Endoxifen generation in vivo is performed by the cytochrome P450 (CYP) 2D6 enzyme <Reference id=36770/><Reference id=36769/><Reference id=36768/><Reference id=36767/>. In addition to its antagonistic activity at estrogen receptors, it also acts as an aromatase inhibitor <Reference id=36773/><Reference id=36772/>.
iupac name: 4-[(~{Z})-1-[4-[2-(methylamino)ethoxy]phenyl]-2-phenylbut-1-enyl]phenol
xref: CHEMBL1093458
synonym: Z-Endoxifen
synonym: N-Desmethyl-4-hydroxytamoxifen
approved: f
ligand name: endoxifen
type: SyntheticOrganicLigand

AM1710
in ch i key: ZAIKPEWFCSQNQB-UHFFFAOYSA-N
in ch i: InChI=1S/C23H28O4/c1-5-6-7-8-11-23(2,3)15-12-19(24)21-18-14-16(26-4)9-10-17(18)22(25)27-20(21)13-15/h9-10,12-14,24H,5-8,11H2,1-4H3
comment: AM1710 is a cannabilactone class, selective cannabinoid CB2 receptor agonist <Reference id=36757/>. The cannabilactones produce peripheral analgesic activity without the the psychoactive central nervous system side-effects of other CB2 receptor agonists <Reference id=36758/>. As expected from its pharmacological profile, AM1710 shows limited blood brain barrier penetration <Reference id=36757/>. It has potent agonist activity at rat and mouse CB2 receptors but much reduced activity at human receptors, so is an excellent tool for rodent studies, but it is less useful for translation-to-human studies. In vitro experiments have identified low-potency CB1 inverse agonist activity, but the in vivo relevance of this discovery is undetermined <Reference id=36759/>.It is important to note that the sequence heterogeneity in CB2 across species leads to different pharmacologic responses to identical drugs <Reference id=36760/>, so extrapolating results from rodent models to humans should be approached with caution. A 2019 publication of work by Li et al. describes rodent experiments that they undertook to resolve the mechanism(s) by which AM1710 suppresses allodynia caused by distinct pathological processes <Reference id=36761/>. Their investigations show that AM1710 is not a broad-spectrum analgesic. In rodent models it is effective in paclitaxel-induced mechanical and cold allodynia but not in mechanically-induced allodynia.
iupac name: 1-hydroxy-9-methoxy-3-(2-methyloctan-2-yl)benzo[c]chromen-6-one
xref: CHEMBL266712
synonym: AM-1710
synonym: AM 1710
synonym: analog 4b [PMID: 18038967]
approved: f
ligand name: AM1710
type: SyntheticOrganicLigand

example 25 [WO2018228934]
in ch i key: UQONAEXHTGDOIH-AWEZNQCLSA-N
in ch i: InChI=1S/C19H24N4O3/c24-16-2-1-7-23(16)14-3-8-22(12-14)18(25)13-10-15-17(20-11-13)21-19(4-5-19)6-9-26-15/h10-11,14H,1-9,12H2,(H,20,21)/t14-/m0/s1
comment: Example 25 is a vanin 1 inhibitor that is claimed in patent WO/2018/228934 <Reference id=36755/>.
iupac name: (3'S)-1'-({3',5'-dihydro-2'H-spiro[cyclopropane-1,4'-pyrido[3,2-b][1,4]oxazepin]-8'-yl}carbonyl)-[1,3'-bipyrrolidin]-2-one
approved: f
ligand name: example 25 [WO2018228934]
type: SyntheticOrganicLigand

migalastat
canonical SMILES: OCC1NCC(C(C1O)O)O
isomeric SMILES: OC[C@H]1NC[C@@H]([C@H]([C@H]1O)O)O
in ch i key: LXBIFEVIBLOUGU-DPYQTVNSSA-N
in ch i: InChI=1S/C6H13NO4/c8-2-3-5(10)6(11)4(9)1-7-3/h3-11H,1-2H2/t3-,4+,5+,6-/m1/s1
comment: Migalastat was developed by Amicus Therapeutics as a first-in-class oral monotherapy for the treatment of Fabry disease <Reference id=36741/>. Mechanistically it acts as a pharmacological chaperone that stabilises certain mutant forms of α-galactosidase that are found in Fabry disease patients and enhances enzyme activity <Reference id=36742/>. It is a stereoisomer of <Ligand id=4642/>.
iupac name: (2R,3S,4R,5S)-2-(hydroxymethyl)piperidine-3,4,5-triol
xref: CHEMBL110458
synonym: GR181413A
synonym: GR-181413A
synonym: Galafold®
synonym: 1-Deoxygalactonojirimycin
approved: t
ligand name: migalastat
type: SyntheticOrganicLigand

tezacaftor
in ch i key: MJUVRTYWUMPBTR-MRXNPFEDSA-N
in ch i: InChI=1S/C26H27F3N2O6/c1-24(2,13-33)22-8-14-7-18(17(27)10-19(14)31(22)11-16(34)12-32)30-23(35)25(5-6-25)15-3-4-20-21(9-15)37-26(28,29)36-20/h3-4,7-10,16,32-34H,5-6,11-13H2,1-2H3,(H,30,35)/t16-/m1/s1
comment: Tezacaftor is a small molecule cystic fibrosis transmembrane conductance regulator (CFTR) modulator that was developed by Vertex Pharmaceuticals <Reference id=36740/>.
iupac name: 1-(2,2-difluoro-1,3-benzodioxol-5-yl)-~{N}-[1-[(2~{R})-2,3-dihydroxypropyl]-6-fluoro-2-(1-hydroxy-2-methylpropan-2-yl)indol-5-yl]cyclopropane-1-carboxamide
xref: CHEMBL3544914
synonym: VX-661
synonym: VX661
synonym: example 315 [US20090131492A1]
approved: t
ligand name: tezacaftor
type: SyntheticOrganicLigand

MBX-2982
in ch i key: NFTMKHWBOINJGM-UHFFFAOYSA-N
in ch i: InChI=1S/C22H24N8OS/c1-2-16-11-23-22(24-12-16)29-9-7-17(8-10-29)21-26-18(14-32-21)13-31-20-5-3-19(4-6-20)30-15-25-27-28-30/h3-6,11-12,14-15,17H,2,7-10,13H2,1H3
comment: MBX-2982 is a GPR119 agonist <Reference id=36619/>, that is a functional activator of human glucokinase activity in vitro <Reference id=36620/>.
iupac name: 2-[1-(5-ethylpyrimidin-2-yl)piperidin-4-yl]-4-[[4-(tetrazol-1-yl)phenoxy]methyl]-1,3-thiazole
xref: CHEMBL3260505
synonym: MBX2982
approved: f
ligand name: MBX-2982
type: SyntheticOrganicLigand

INT-767
in ch i key: XGIYOABXZNJOHV-APIYUPOTSA-M
in ch i: InChI=1S/C25H44O6S/c1-5-17-21-14-16(26)8-11-25(21,4)20-9-12-24(3)18(6-7-19(24)22(20)23(17)27)15(2)10-13-31-32(28,29)30/h15-23,26-27H,5-14H2,1-4H3,(H,28,29,30)/p-1/t15-,16-,17-,18-,19+,20+,21+,22+,23-,24-,25-/m1/s1
comment: INT-767 is a dual farnesoid X receptor (FXR) and G protein-coupled bile acid receptor 1 (TGR5) agonist that is in Intercept Pharmaceuticals' development pipeline <Reference id=36732/>. Chemically it is a semisynthetic bile acid derivative and it was synthesised and tested as the sodium salt. Preclinical data indicate INT-767's potential in both preventing and reversing organ damage due to fibrosis.
xref: CHEMBL3306873
synonym: INT767
synonym: 6α-ethyl-3α,7α,23-trihydroxy-24-nor-5β-cholan-23-sulfate
approved: f
ligand name: INT-767
type: SyntheticOrganicLigand

VU6012962
in ch i key: IQNLJJLZIVCGFI-UHFFFAOYSA-N
in ch i: InChI=1S/C21H19F3N4O4/c1-30-19-8-14(4-7-18(19)31-10-13-2-3-13)20(29)27-16-9-15(32-21(22,23)24)5-6-17(16)28-12-25-11-26-28/h4-9,11-13H,2-3,10H2,1H3,(H,27,29)
comment: VU6012962 is an orally bioavailable, CNS-penetrant negative allosteric modulator of glutamate metabotropic receptor 7 (mGlu7) that is suitable as a research probe <Reference id=36727/>.
iupac name: 4-(cyclopropylmethoxy)-3-methoxy-N-[2-(1H-1,2,4-triazol-1-yl)-5-(trifluoromethoxy)phenyl]benzamide
synonym: compound 7d [PMID: 30608678]
approved: f
ligand name: VU6012962
type: SyntheticOrganicLigand

compound 28 [PMID: 30624936]
in ch i key: WPKXXVMGORDACP-GFCCVEGCSA-N
in ch i: InChI=1S/C23H25N5O2/c1-12-17-15(19(29)24-12)11-16(25-17)13-5-4-6-14-18(13)26-21(27-22(2)7-8-22)28(20(14)30)23(3)9-10-23/h4-6,11-12,25H,7-10H2,1-3H3,(H,24,29)(H,26,27)/t12-/m1/s1
comment: Compound 28 is a selective PIM1/2 kinase inhibitor that has been designed for therapeutic potential in treating hematological malignancies <Reference id=36726/>.
iupac name: 3-(1-methylcyclopropyl)-2-[(1-methylcyclopropyl)amino]-8-[(6~{R})-6-methyl-4-oxo-5,6-dihydro-1~{H}-pyrrolo[3,4-b]pyrrol-2-yl]quinazolin-4-one
approved: f
ligand name: compound 28 [PMID: 30624936]
type: SyntheticOrganicLigand

compound 6g [PMID: 30633509]
in ch i key: IXKCNJIWRNIRNO-UHFFFAOYSA-N
in ch i: InChI=1S/C22H21N3O3S/c1-13-5-7-14(8-6-13)19-11-16-21(29-19)22(24-12-23-16)25-15-9-17(26-2)20(28-4)18(10-15)27-3/h5-12H,1-4H3,(H,23,24,25)
comment: Compound 6g was desigend as a dual epidermal growth factor receptor (EGFR) kinase and tubulin polymerization inhibitor <Reference id=36725/>. It binds to the colchicine site on tubulin which is expected to translate to antimitotic activity and it should mediate a vascular-disrupting effect via EGFR inhibition.
iupac name: 6-(p-Tolyl)-N-(3,4,5-trimethoxyphenyl)thieno[3,2-d]pyrimidin-4-amine
approved: f
ligand name: compound 6g [PMID: 30633509]
type: SyntheticOrganicLigand

PBF-509
canonical SMILES: Nc1nc(nc(c1Br)n1cccn1)n1cccn1
isomeric SMILES: Nc1nc(nc(c1Br)n1cccn1)n1cccn1
in ch i key: ATFXVNUWQOXRRU-UHFFFAOYSA-N
in ch i: InChI=1S/C10H8BrN7/c11-7-8(12)15-10(18-6-2-4-14-18)16-9(7)17-5-1-3-13-17/h1-6H,(H2,12,15,16)
comment: PBF-509 is an adenosine A2A receptor antagonist that is being developed by Palobiofarma <Reference id=33545/><Reference id=36722/>. It is being considered for clinical potential as an immuno-onclogy adjunctive agent and as a treatment for movement disorder in Parkinson's disease patients. Although the chemical structure of PBF-509 has not been formally disclosed, a comparision of published data and Palobiofarma patent documents leads us to consider Example 1 from WO2011121418A1 <Reference id=36723/> as a likely candidate for this antagonist (binding and functional data values in the patent match data published in the peer reviewed articles that describe PBF-509). We await full disclosure to be certain of our decision.
iupac name: 5-bromo-2,6-di(pyrazol-1-yl)pyrimidin-4-amine
xref: CHEMBL3638684
synonym: PBF509
approved: f
ligand name: PBF-509
type: SyntheticOrganicLigand

ADU-S100
in ch i key: IZJJFUQKKZFVLH-LTKSHMRXSA-N
comment: ADU-S100 (a.k.a. ML RR-S2 CDA) is a synthetic cyclic dinucleotide STING agonist that is being developed as an immuno-oncology lead by Aduro BioTech and Novartis <Reference id=36721/>.
synonym: S100
synonym: ML RR-S2 CDA
synonym: MIW815
synonym: dithio-(Rp,Rp)-[cyclic[A(2',5')pA(3',5')p]]
approved: f
ligand name: ADU-S100
type: SyntheticOrganicLigand

BMS-1001
canonical SMILES: OCC(C(=O)O)NCc1cc(C)c(cc1OCc1cccc(c1)C#N)OCc1cccc(c1C)c1ccc2c(c1)OCCO2
isomeric SMILES: OCC(C(=O)O)NCc1cc(C)c(cc1OCc1cccc(c1)C#N)OCc1cccc(c1C)c1ccc2c(c1)OCCO2
in ch i key: UWNXGZKSIKQKAH-UHFFFAOYSA-N
in ch i: InChI=1S/C35H34N2O7/c1-22-13-28(18-37-30(19-38)35(39)40)33(43-20-25-6-3-5-24(14-25)17-36)16-32(22)44-21-27-7-4-8-29(23(27)2)26-9-10-31-34(15-26)42-12-11-41-31/h3-10,13-16,30,37-38H,11-12,18-21H2,1-2H3,(H,39,40)
comment: BMS-1001 is a small molecule that disrupts the PD-1/PD-L1 immune checkpoint interaction from the same series as <Ligand id=9608/> <Reference id=36712/>.
synonym: BMS1001
synonym: Example 1001 [WO2015160641A2]
approved: f
ligand name: BMS-1001
type: SyntheticOrganicLigand

ciforadenant
in ch i key: KURQKNMKCGYWRJ-HNNXBMFYSA-N
in ch i: InChI=1S/C20H21N7O3/c1-12-5-6-16(30-12)17-18-19(24-20(21)23-17)27(26-25-18)9-13-3-2-4-14(22-13)10-29-15-7-8-28-11-15/h2-6,15H,7-11H2,1H3,(H2,21,23,24)/t15-/m0/s1
comment: Ciforadenant (CPI-444) is an orally active adenosine A2A receptor antagonist.
iupac name: 7-(5-methylfuran-2-yl)-3-[[6-[[(3S)-oxolan-3-yl]oxymethyl]pyridin-2-yl]methyl]triazolo[4,5-d]pyrimidin-5-amine
synonym: CPI-444
synonym: CPI444
synonym: V81444
synonym: V-81444
approved: f
ligand name: ciforadenant
type: SyntheticOrganicLigand

compound 3f [Festa et al., 2019]
canonical SMILES: N1CCC(CC1)c1onc(n1)c1ccc2c(c1)cccc2
isomeric SMILES: N1CCC(CC1)c1onc(n1)c1ccc2c(c1)cccc2
in ch i key: PPCNFLPYHQIYHP-UHFFFAOYSA-N
in ch i: InChI=1S/C17H17N3O/c1-2-4-14-11-15(6-5-12(14)3-1)16-19-17(21-20-16)13-7-9-18-10-8-13/h1-6,11,13,18H,7-10H2
comment: Compound 3f is a non-steroidal, selective farnesoid X receptor (FXR) antagonist with a novel 3,5-disubstituted oxadiazole chemotype <Reference id=36680/>. It is proposed as a promising lead that is suitable to further the investigation of the therapeutic value of FXR antagonists in the treatment of cholestasis and related metabolic disorders. Antagonist binding to FXR renders the receptor unable to recruit the coactivators it requires for transcriptional activation, and results instead in transcriptional silencing of FXR target genes. 3f exhibits no agonistic activity toward FXR.
approved: f
ligand name: compound 3f [Festa et al., 2019]
type: SyntheticOrganicLigand

compound 28 [Heitel et al., 2019]
canonical SMILES: CC(=O)c1ccc(cc1)COc1ccccc1c1ccccc1
isomeric SMILES: CC(=O)c1ccc(cc1)COc1ccccc1c1ccccc1
in ch i key: ZYZDLKZAFQVEKA-UHFFFAOYSA-N
in ch i: InChI=1S/C21H18O2/c1-16(22)18-13-11-17(12-14-18)15-23-21-10-6-5-9-20(21)19-7-3-2-4-8-19/h2-14H,15H2,1H3
comment: Compound 28 is a retinoid X receptor agonist (rexinoid) <Reference id=36679/> and is representative of a novel rexinoid chemotype that is proposed as a lead for the RXR-targeting medicinal chemistry pipeline.
iupac name: 1-[4-({[1,1'-biphenyl]-2-yloxy}methyl)phenyl]ethan-1-one
approved: f
ligand name: compound 28 [Heitel et al., 2019]
type: SyntheticOrganicLigand

NFP
in ch i key: JRUPWWCGTBJDNY-LNMFUWNLSA-N
in ch i: InChI=1S/C26H28FN3O4/c27-17-12-28-9-6-16(17)24(32)29-18-5-7-26(33)20-11-15-3-4-19(31)22-21(15)25(26,23(18)34-22)8-10-30(20)13-14-1-2-14/h3-4,6,9,12,14,18,20,23,31,33H,1-2,5,7-8,10-11,13H2,(H,29,32)/t18-,20-,23+,25?,26-/m1/s1
comment: NFP is a μ/κ opioid receptor dual selective antagonist. It is able to cross the blood-brain barrier so acts both centrally and peripherally <Reference id=36678/>. In vivo evidence suggests NFP as a lead compound in the search for new agents to treat opioid abuse and addiction.
iupac name: 17-Cyclopropylmethyl-3,14β-dihydroxy-4,5α-epoxy-6β-[(3'-fluoro-4'-pyridyl)acetamido]morphinan
synonym: compound 1 [PMID: 30608693]
approved: f
ligand name: NFP
type: SyntheticOrganicLigand

BAY-885
in ch i key: QXURFIGBRGWPQD-UHFFFAOYSA-N
in ch i: InChI=1S/C25H28F3N7O2/c1-33-8-10-34(11-9-33)17-12-21-23(30-14-17)22(32-15-31-21)16-4-6-35(7-5-16)24(36)19-3-2-18(13-20(19)29)37-25(26,27)28/h2-3,12-16H,4-11,29H2,1H3
comment: BAY-885 is a tool compound for studying the function of ERK5 (MAPK7) in cellular signalling, particularly its role in cancer cell proliferation <Reference id=36668/>. The compound has been used to show that pharmacological inhibition of ERK5 does not recapitulate the antiproliferative effects observed with genetic depletion of ERK5, findings which cast doubt on the role of ERK5 as a therapeutic target for cancer cell growth.
iupac name: [2-amino-4-(trifluoromethoxy)phenyl]-[4-[7-(4-methylpiperazin-1-yl)pyrido[3,2-d]pyrimidin-4-yl]piperidin-1-yl]methanone
synonym: compound 41 [PMID: 30563338]
synonym: BAY885
approved: f
ligand name: BAY-885
type: SyntheticOrganicLigand

vidupiprant
in ch i key: PFWVGKROPKKEDW-UHFFFAOYSA-N
comment: Vidupiprant (AMG853) is a dual prostanoid DP1 and DP2 receptor antagonist that was developed for anti-asthmatic potential <Reference id=36627/>.
iupac name: 2-[4-[4-(tert-butylcarbamoyl)-2-[(2-chloro-4-cyclopropylphenyl)sulfonylamino]phenoxy]-5-chloro-2-fluorophenyl]acetic acid
xref: CHEMBL1951575
synonym: AMG853
synonym: AMG-853
synonym: AMG 853
synonym: compound 2 [PMID: 24900313]
approved: f
ligand name: vidupiprant
type: SyntheticOrganicLigand

tomivosertib
in ch i key: HKTBYUWLRDZAJK-UHFFFAOYSA-N
in ch i: InChI=1S/C17H20N6O2/c1-10-7-11(21-13-8-12(18)19-9-20-13)16(25)23-14(10)15(24)22-17(23)5-3-2-4-6-17/h7-9H,2-6H2,1H3,(H,22,24)(H3,18,19,20,21)
comment: Tomivosertib (eFT508) is an orally active and selective mitogen-activated protein kinase interacting kinases 1 and 2 (MNK1/2) inhibitor that is being developed by eFFECTOR Therapeutics for anti-neoplastic potential <Reference id=36621/>.
iupac name: 6-[(6-aminopyrimidin-4-yl)amino]-8-methylspiro[2H-imidazo[1,5-a]pyridine-3,1'-cyclohexane]-1,5-dione
synonym: eFT508
synonym: compound 23 [PMID: 29526098]
synonym: eFT-508
approved: f
ligand name: tomivosertib
type: SyntheticOrganicLigand

ARD-69
in ch i key: CWGVEMFBQJUWLU-RXFAPWBBSA-N
comment: ARD-69 is a potent proteolysis-targeting chimera (PROTAC) degrader of the androgen receptor (AR) that was designed as a proof-of-concept lead to evaluate the potential of PROTAC technology as a novel treatment mechanism for AR-positive, castration-resistant prostate cancer <Reference id=36666/>. It contains an AR antagonist (reported in <Reference id=36667/>) that binds the AR, joined by a small linker molecule to a second ligand (in this case a VHL ligand) that engages the E3 ubiquitin ligase system via Cullin-2. This chimeric molecular structure targets AR protein for ubiquitination-dependent proteolysis.
synonym: compound 34 [PMID: 30629437]
synonym: ARD69
approved: f
ligand name: ARD-69
type: SyntheticOrganicLigand

compound 19a [PMID: 30503936]
in ch i key: GZVQZLVAKXRTHU-UHFFFAOYSA-N
comment: Compound 19a was designed as a small molecule type II kinase inhibitor to target c-Met in cancers, with improved drug-like properties, and pharmacokinetic and toxicity profiles compared to previously reported inhibitors of c-Met <Reference id=36665/>. It is a multi-tyrosine kinase inhibitor with targets including c-Met, Ron (macrophage stimulating 1 receptor), c-Kit, AXL and IGF-1R, and it is reported to be effective against drug-sensitive and drug-resistant cancer cell lines.
approved: f
ligand name: compound 19a [PMID: 30503936]
type: SyntheticOrganicLigand

setipiprant
in ch i key: IHAXLPDVOWLUOS-UHFFFAOYSA-N
in ch i: InChI=1S/C24H19FN2O3/c25-16-8-9-21-19(12-16)20-13-26(11-10-22(20)27(21)14-23(28)29)24(30)18-7-3-5-15-4-1-2-6-17(15)18/h1-9,12H,10-11,13-14H2,(H,28,29)
comment: Setipiprant (ACT-129968) is an orally active, potent and selective prostaglandin D2 (PGD2) receptor 2 (DP2 receptor) antagonist <Reference id=36655/>.
iupac name: 2-[8-fluoro-2-(naphthalene-1-carbonyl)-3,4-dihydro-1H-pyrido[4,3-b]indol-5-yl]acetic acid
xref: CHEMBL2386081
synonym: ACT-129968
synonym: ACT129968
synonym: compound 28 [PMID: 23721423]
approved: f
ligand name: setipiprant
type: SyntheticOrganicLigand

ARRY-502
in ch i key: QIDYUNXQPQEJEC-IBGZPJMESA-N
in ch i: InChI=1S/C26H23Cl2NO6/c1-33-22-12-17(27)5-2-15(22)8-10-29-25(30)16-3-6-18(7-4-16)35-24-14-23-20(13-21(24)28)19(26(31)32)9-11-34-23/h2-7,12-14,19H,8-11H2,1H3,(H,29,30)(H,31,32)/t19-/m0/s1
comment: ARRY-502 is an oral, potent and selective prostaglandin D2 receptor 2 (DP2) antagonist. It is the (4S) enantiomer of one of the chemical structures (example 237) claimed in Array Biopharma's patent WO2009158426A1
synonym: ARRY502
synonym: example 237, enantiomer 1 [WO2009158426A1]
approved: f
ligand name: ARRY-502
type: SyntheticOrganicLigand

MDMB-Fubinaca
in ch i key: RFCDVEHNYDVCMU-LJQANCHMSA-N
in ch i: InChI=1S/C22H24FN3O3/c1-22(2,3)19(21(28)29-4)24-20(27)18-16-7-5-6-8-17(16)26(25-18)13-14-9-11-15(23)12-10-14/h5-12,19H,13H2,1-4H3,(H,24,27)/t19-/m1/s1
comment: MDMB-Fubinaca is an extremely potent, synthetic cannabinoid CB1/CB2 receptor agonist <Reference id=36649/>. Cryo-EM of the ligand-receptor complex shows that it locks the CB1 receptor in an active conformation <Reference id=36650/>.
iupac name: methyl (2S)-2-[[1-[(4-fluorophenyl)methyl]indazole-3-carbonyl]amino]-3,3-dimethylbutanoate
synonym: Fub-mdmb
synonym: Mdmb-bz-F
synonym: Mdmb-fub
approved: f
ligand name: MDMB-Fubinaca
type: SyntheticOrganicLigand

AM10257
in ch i key: FMJXYCCDMAGPLE-UHFFFAOYSA-N
in ch i: InChI=1S/C26H35N3O2/c1-18-23(25(31)27-26-15-19-12-20(16-26)14-21(13-19)17-26)28-29(10-6-3-7-11-30)24(18)22-8-4-2-5-9-22/h2,4-5,8-9,19-21,30H,3,6-7,10-17H2,1H3,(H,27,31)
comment: AM10257 is a high affinity antagonist/inverse agonist of the cannabinoid CB2 receptor <Reference id=36648/>. Low efficacy CB1 agonism has also been detected.
iupac name: N-(adamantan-1-yl)-1-(5-hydroxypentyl)-4-methyl-5-phenyl-1H-pyrazole-3-carboxamide
synonym: AM-10257
approved: f
ligand name: AM10257
type: SyntheticOrganicLigand

ubrogepant
in ch i key: DDOOFTLHJSMHLN-ZQHRPCGSSA-N
in ch i: InChI=1S/C29H26F3N5O3/c1-16-20(17-6-3-2-4-7-17)11-22(26(39)37(16)15-29(30,31)32)35-25(38)19-10-18-12-28(13-23(18)34-14-19)21-8-5-9-33-24(21)36-27(28)40/h2-10,14,16,20,22H,11-13,15H2,1H3,(H,35,38)(H,33,36,40)/t16-,20-,22+,28+/m1/s1
comment: Ubrogepant (MK-1602) is an orally available calcitonin gene-related peptide receptor antagonist that was developed by Allergan for the acute treatment of migraine <Reference id=36646/><Reference id=35078/><Reference id=36645/><Reference id=36644/>. Notably it was the first oral CGRP receptor antagonist to be approved to treat migraines as they are occurring. Previously approved CGRP/CGRP receptor-targeting drugs (e.g. <Ligand id=9208/>, <Ligand id=8967/> and <Ligand id=9250/>) have been indicated for migraine prevention.
iupac name: (3S)-N-[(3S,5S,6R)-6-methyl-2-oxo-5-phenyl-1-(2,2,2-trifluoroethyl)piperidin-3-yl]-2-oxospiro[1H-pyrrolo[2,3-b]pyridine-3,6'-5,7-dihydrocyclopenta[b]pyridine]-3'-carboxamide
xref: CHEMBL2364638
synonym: Ubrelvy®
synonym: MK-1602
synonym: MK1602
approved: t
ligand name: ubrogepant
type: SyntheticOrganicLigand

SC83288
in ch i key: UJKWTQWUYKHLGQ-UHFFFAOYSA-N
in ch i: InChI=1S/C27H31N7O7S2/c1-41-27(36)34-15-13-33(14-16-34)25(28)20-3-2-4-22(17-20)32-26(35)31-21-7-11-24(12-8-21)43(39,40)30-18-19-5-9-23(10-6-19)42(29,37)38/h2-12,17,28,30H,13-16,18H2,1H3,(H2,29,37,38)(H2,31,32,35)
comment: SC83288 is an amicarbalide derivative and the clinical development candidate for this novel antimalarial chemotype <Reference id=36639/>. The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
iupac name: methyl 4-[3-[[4-[(4-sulfamoylphenyl)methylsulfamoyl]phenyl]carbamoylamino]benzenecarboximidoyl]piperazine-1-carboxylate
approved: f
ligand name: SC83288
type: SyntheticOrganicLigand

sulfalene
canonical SMILES: COc1nccnc1NS(=O)(=O)c1ccc(cc1)N
isomeric SMILES: COc1nccnc1NS(=O)(=O)c1ccc(cc1)N
in ch i key: KXRZBTAEDBELFD-UHFFFAOYSA-N
in ch i: InChI=1S/C11H12N4O3S/c1-18-11-10(13-6-7-14-11)15-19(16,17)9-4-2-8(12)3-5-9/h2-7H,12H2,1H3,(H,13,15)
comment: Sulfalene is a sulfonamide containing compound with antimalarial activity. The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
iupac name: 4-amino-N-(3-methoxypyrazin-2-yl)benzenesulfonamide
xref: CHEMBL1525826
synonym: sulfamethopyrazine
synonym: sulfametopyrazine
synonym: Kelfizine®
synonym: sulfamethoxypyrazine
approved: f
ligand name: sulfalene
type: SyntheticOrganicLigand

mepacrine
in ch i key: GPKJTRJOBQGKQK-UHFFFAOYSA-N
in ch i: InChI=1S/C23H30ClN3O/c1-5-27(6-2)13-7-8-16(3)25-23-19-11-9-17(24)14-22(19)26-21-12-10-18(28-4)15-20(21)23/h9-12,14-16H,5-8,13H2,1-4H3,(H,25,26)
comment: Mepacrine is an acridine derivative with antiprotozoal activity. Historically used as an antimalarial drug it is now used off-license as an immunomodulatory agent. The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
iupac name: N'-(6-chloro-2-methoxyacridin-9-yl)-N,N-diethylpentane-1,4-diamine
xref: CHEMBL7568
synonym: quinacrine
synonym: Atabrine®
approved: f
ligand name: mepacrine
type: SyntheticOrganicLigand

GLPG1205
in ch i key: IRBAWVGZNJIROV-SFHVURJKSA-N
in ch i: InChI=1S/C22H22N2O4/c25-22-23-21(28-14-18-13-26-9-10-27-18)12-20-19-6-5-16(4-3-15-1-2-15)11-17(19)7-8-24(20)22/h5-6,11-12,15,18H,1-2,7-10,13-14H2/t18-/m0/s1
comment: GLPG1205 is an investigational, orally bioavailable GPR84 antagonist that was being developed by Galapagos. The chemical structure is claimed as compound 122 in patent WO2013092791A1, for the treatment of inflammatory disorders <Reference id=36636/>. Galapagos cut GLPG1205 (for idiopathic pulmonary fibrosis, IPF) from their development pipeline in a cost-cutting exercise in the first half of 2021. Their chitinase inhibitor, GLPG4617 (structure undisclosed), will be taken forward into a phase 2 study for IPF.
iupac name: 9-(2-cyclopropylethynyl)-2-[[(2S)-1,4-dioxan-2-yl]methoxy]-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one
synonym: GLPG-1205
synonym: compound 122 [WO2013092791A1]
approved: f
ligand name: GLPG1205
type: SyntheticOrganicLigand

AM-461
in ch i key: SDHFXINHZHARIB-UHFFFAOYSA-N
in ch i: InChI=1S/C25H33NO5S/c1-24(2,3)23(29)26-18-9-11-19(17(14-18)15-32-25(4,5)6)31-21-12-16(13-22(27)28)8-10-20(21)30-7/h8-12,14H,13,15H2,1-7H3,(H,26,29)(H,27,28)
comment: AM-461 is a prostanoid DP2 receptor antagonist. It is one of the chemical structures claimed (Compound 1) in patent WO2011085033 for use in treating PGD2-mediated inflammatory allergic responses, particularly asthmatic symptoms <Reference id=36629/>.
iupac name: 2-[3-[2-(tert-butylsulfanylmethyl)-4-(2,2-dimethylpropanoylamino)phenoxy]-4-methoxyphenyl]acetic acid
synonym: AM461
synonym: AM 461
synonym: Compound 1 [WO2011085033]
approved: f
ligand name: AM-461
type: SyntheticOrganicLigand

neolymphostin A
in ch i key: OKZVXALNOKYCRL-SNAWJCMRSA-N
in ch i: InChI=1S/C18H18N4O3/c1-9(2)18(24)22-13-7-11(19)16-15-10(8-20-16)6-12(21-17(13)15)14(23)4-5-25-3/h4-9H,19H2,1-3H3,(H,22,24)/b5-4+
comment: Neolymphostin A is a natural product that was isolated from the marine actinomycetes bacterium Salinispora arenicola CNY-486 <Reference id=36527/>. It was shown to be a dual inhibitor of PI3K/mTOR in vitro. It covalently modifies Lys802 of human PI3Kα in tandem MS/MS experiments. This is claimed to be the first example of a covalent kinase inhibitor to be isolated from bacteria.
synonym: compound 4 [PMID: 30380865]
approved: f
ligand name: neolymphostin A
type: SyntheticOrganicLigand

SX682
in ch i key: SDUDZBCEHIZMFZ-UHFFFAOYSA-N
comment: SX682 is a selective and reversible antagonist (negative allosteric modulator) of the C-X-C motif chemokine receptors CXCR1 and CXCR2. It is orally bioavailable and is being investigated for potential anti-inflammatory and antineoplastic activities. It was developed by Syntrix Pharmaceuticals. The chemical structure presented here was obtained from the NIH's NCI drug Dictionary
iupac name: [2-[[5-[(4-fluorophenyl)carbamoyl]pyrimidin-2-yl]sulfanylmethyl]-4-(trifluoromethoxy)phenyl]boronic acid
approved: f
ligand name: SX682
type: SyntheticOrganicLigand

CCX354
in ch i key: WSVDLXWYJRCDBZ-UHFFFAOYSA-N
in ch i: InChI=1S/C22H22ClN7O2/c1-32-18-13-15(4-5-17(18)23)28-9-11-29(12-10-28)19(31)14-30-22-16(3-2-6-26-22)20(27-30)21-24-7-8-25-21/h2-8,13,27H,9-12,14H2,1H3
comment: CCX354 is an orally active CCR1 antagonist that was originally developed by Chemocentryx for anti-inflammatory/immunomodulatory potential. The chemical structure is claimed as Example 16 in patent WO2008147815A1 <Reference id=36604/>. The structure in the patent resolves to PubChem CID 25016615, which is a tautomeric representation of the claimed structure.
iupac name: 1-[4-(4-chloro-3-methoxyphenyl)piperazin-1-yl]-2-(3-imidazol-2-ylidene-2H-pyrazolo[3,4-b]pyridin-1-yl)ethanone
synonym: CCX-354
synonym: CCX 354
synonym: CCX-354-C
approved: f
ligand name: CCX354
type: SyntheticOrganicLigand

RV6153
in ch i key: JTACVHJPXOKMTI-UHFFFAOYSA-N
in ch i: InChI=1S/C36H31F4N7O5/c1-50-12-13-52-15-14-51-11-5-8-22-7-4-10-28-30(22)35(49)46(19-23-6-2-3-9-27(23)36(38,39)40)29(44-28)20-47-34-31(33(41)42-21-43-34)32(45-47)24-16-25(37)18-26(48)17-24/h2-4,6-7,9-10,16-18,21,48H,11-15,19-20H2,1H3,(H2,41,42,43)
comment: RV6153 is a clinical stage PI3Kγδ inhibitor <Reference id=36576/> that is being developed by Janssen Biotech subsidiary RespiVert. The chemical structure is claimed in patent US9227977B2 <Reference id=36577/>. It is a derivative of <Ligand id=10162/>. RV6153 is selective for PI3Kγδ over the α and β enzyme isoforms.
xref: CHEMBL3934989
synonym: RV-6153
approved: f
ligand name: RV6153
type: SyntheticOrganicLigand

RV1729
in ch i key: UBLOHCIYTDRGJH-UHFFFAOYSA-N
in ch i: InChI=1S/C39H39ClN8O5/c1-52-20-18-46(19-21-53-2)33(50)17-5-3-4-10-26-12-9-16-31-34(26)39(51)47(23-28-11-6-7-15-30(28)40)32(44-31)24-48-38-35(37(41)42-25-43-38)36(45-48)27-13-8-14-29(49)22-27/h6-9,11-16,22,25,49H,3,5,17-21,23-24H2,1-2H3,(H2,41,42,43)
comment: RV1729 is a clinical stage PI3Kγδ inhibitor that is being developed by Janssen Biotech subsidiary RespiVert (and licensed to Pulmatrix in 2017). The chemical structure is claimed in patent WO/2012/052753 <Reference id=36574/><Reference id=36575/>.
iupac name: 6-[2-[[4-amino-3-(3-hydroxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]methyl]-3-[(2-chlorophenyl)methyl]-4-oxoquinazolin-5-yl]-N,N-bis(2-methoxyethyl)hex-5-ynamide
xref: CHEMBL3919512
synonym: RV-1729
approved: f
ligand name: RV1729
type: SyntheticOrganicLigand

DMAMCL
canonical SMILES: C[NH+](CC1C(=O)OC2C1CCC(=C1C2C(C)(O)CC1)C)C
in ch i key: ZPBIJIIQXPRJSS-WNZSCWOMSA-O
in ch i: InChI=1S/C17H27NO3/c1-10-5-6-12-13(9-18(3)4)16(19)21-15(12)14-11(10)7-8-17(14,2)20/h12-15,20H,5-9H2,1-4H3/p+1/t12-,13-,14-,15-,17+/m0/s1
comment: DMAMCL (dimethylaminomicheliolide) is a Michael adduct of micheliolide (a natural plant-derived guaianolide sesquiterpene lactone; PubChem CID 442279) <Reference id=34978/>. It was originally identified for its ability to inhibit acute myelogenous leukemia (AML) stem and progenitor cells. More recently its mechanism of action has been determined <Reference id=34979/>. It induces irreversible tetramerization of PKM2 and acts as a functional activator of PKM2 pyruvate kinase activity. This mechanism is being exploited as a potential anti-cancer therapeutic, with an orally active DMAMCL prodrug (ACT001) in early clinical trial (in Australian trial ACTRN12616000228482) in patients with advanced solid tumours, including glioblastoma multiforme (GBM).
iupac name: {[(3R,3aS,9R,9aS,9bS)-9-hydroxy-6,9-dimethyl-2-oxo-2H,3H,3aH,4H,5H,7H,8H,9H,9aH,9bH-azuleno[4,5-b]furan-3-yl]methyl}dimethylazanium
synonym: compound 21 [PMID: 22985027]
synonym: dimethylaminomicheliolide
approved: f
ligand name: DMAMCL
type: SyntheticOrganicLigand

VK-II-86
in ch i key: OHYHNEODRHJYSS-UHFFFAOYSA-N
in ch i: InChI=1S/C25H28N2O4/c1-29-22-10-4-5-11-23(22)31-16-14-26-17-18(28)13-15-30-24-12-6-9-21-25(24)19-7-2-3-8-20(19)27-21/h2-12,18,26-28H,13-17H2,1H3
comment: VK-II-86 is a <Ligand id=551/> analogue <Reference id=36570/>. It has been used to demonstrate inhibition of store-overload-induced calcium release (SOICR) through the ryanodine receptor 2 (RyR2) channel.
iupac name: 4-(9H-carbazol-4-yloxy)-1-[2-(2-methoxyphenoxy)ethylamino]butan-2-ol
xref: CHEMBL2440787
synonym: compound 8 [PMID: 24124794]
approved: f
ligand name: VK-II-86
type: SyntheticOrganicLigand

nilvadipine
canonical SMILES: COC(=O)C1=C(C#N)NC(=C(C1c1cccc(c1)[N+](=O)[O-])C(=O)OC(C)C)C
isomeric SMILES: COC(=O)C1=C(C#N)NC(=C(C1c1cccc(c1)[N+](=O)[O-])C(=O)OC(C)C)C
in ch i key: FAIIFDPAEUKBEP-UHFFFAOYSA-N
in ch i: InChI=1S/C19H19N3O6/c1-10(2)28-19(24)15-11(3)21-14(9-20)17(18(23)27-4)16(15)12-6-5-7-13(8-12)22(25)26/h5-8,10,16,21H,1-4H3
comment: Nilvadipine is a dihydropyridine class L-type calcium channel blocker that is used as an anti-hypertensive drug <Reference id=36568/>. The INN indicates that nilvadipine is a mixture of enantiomers. We show the chemical structure without specified stereochemistry to represent the mixture.
xref: CHEMBL517427
synonym: FR-34235
synonym: FR34235
synonym: Escor®
approved: f
ligand name: nilvadipine
type: SyntheticOrganicLigand

benidipine
canonical SMILES: COC(=O)C1=C(C)NC(=C(C1c1cccc(c1)[N+](=O)[O-])C(=O)OC1CCCN(C1)Cc1ccccc1)C
isomeric SMILES: COC(=O)C1=C(C)NC(=C(C1c1cccc(c1)[N+](=O)[O-])C(=O)OC1CCCN(C1)Cc1ccccc1)C
in ch i key: QZVNQOLPLYWLHQ-UHFFFAOYSA-N
in ch i: InChI=1S/C28H31N3O6/c1-18-24(27(32)36-3)26(21-11-7-12-22(15-21)31(34)35)25(19(2)29-18)28(33)37-23-13-8-14-30(17-23)16-20-9-5-4-6-10-20/h4-7,9-12,15,23,26,29H,8,13-14,16-17H2,1-3H3
comment: Benidipine is a dihydropyridine class, triple L-, T-, and N-type calcium channel blocker. The approved drug is a mixture of enantiomers and is administered as the hydrochloride salt. We show the chemical structure without specified stereochemistry to represent the mixture. The consensus PubChem compound for benidipine is CID 656668.
synonym: Coniel®
approved: t
ligand name: benidipine
type: SyntheticOrganicLigand

BMS-823778
in ch i key: PTIFVLOBVCIMKL-UHFFFAOYSA-N
in ch i: InChI=1S/C18H18ClN3O/c1-17(2,23)14-4-3-11-22-15(14)20-21-16(22)18(9-10-18)12-5-7-13(19)8-6-12/h3-8,11,23H,9-10H2,1-2H3
comment: BMS-823778 is an orally bioavailable clinical lead inhibitor of hydroxysteroid 11-beta dehydrogenase 1 (11β-HSD) <Reference id=36562/> which is the enzyme that converts inactive cortisone to biologically active costisol <Reference id=36563/>. We show the chemical structure for BMS-823778 free base. Some bioactivity data may have been determined using the hydrochloride salt (PubChem CID 54669979). BMS-823778 was developed for potential treatment of type 2 diabetes and metabolic syndrome.
iupac name: 2-[3-[1-(4-chlorophenyl)cyclopropyl]-[1,2,4]triazolo[4,3-a]pyridin-8-yl]propan-2-ol
synonym: compound 2 [Li et al., 2018]
approved: f
ligand name: BMS-823778
type: SyntheticOrganicLigand

JAK3 inhibitor 34
in ch i key: LOSIDNZHKAVMKF-IBGZPJMESA-N
in ch i: InChI=1S/C22H17N5/c23-12-25-19-9-8-15-6-7-16(10-17(15)19)21-20-18(14-4-2-1-3-5-14)11-24-22(20)27-13-26-21/h1-7,10-11,13,19,25H,8-9H2,(H,24,26,27)/t19-/m0/s1
comment: Compound 34 is an exemplar selective and covalent Janus kinase 3 (JAK3) inhibitor that was discovered by Casimiro-Garcia et al. <Reference id=36554/>. It was designed such that its cyanamide group directly engages the Cys909 residue in JAK3.
iupac name: (S)-N-(6-(5-Phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-2,3-dihydro-1H-inden-1-yl)cyanamide
synonym: compound 34 [PMID: 30423248]
approved: f
ligand name: JAK3 inhibitor 34
type: SyntheticOrganicLigand

JAK3 inhibitor 32
in ch i key: MLJSOTTYIVCEQO-VQTJNVASSA-N
in ch i: InChI=1S/C22H17FN6O2S/c23-14-2-1-3-15(9-14)32(30,31)29-20-10-19(26-11-24)18-8-13(4-5-16(18)20)21-17-6-7-25-22(17)28-12-27-21/h1-9,12,19-20,26,29H,10H2,(H,25,27,28)/t19-,20+/m0/s1
comment: Compound 32 is an exemplar selective and covalent Janus kinase 3 (JAK3) inhibitor that was discovered by Casimiro-Garcia et al. <Reference id=36554/>. It was designed such that its cyanamide group directly engages the Cys909 residue in JAK3, and it exhibits irreversible binding in a competition binding assay.
iupac name: N-((1R,3S)-3-Cyanamido-5-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-2,3-dihydro-1H-inden-1-yl)-3-cyanobenzenesulfonamide
synonym: compound 32 [PMID: 30423248]
approved: f
ligand name: JAK3 inhibitor 32
type: SyntheticOrganicLigand

RIPK1 inhibitor 22b
in ch i key: APPXQUDJLJXULP-UHFFFAOYSA-N
in ch i: InChI=1S/C25H22F3N5O2/c1-2-32-13-19(22-23(29)30-14-31-24(22)32)16-6-7-20-17(12-16)8-9-33(20)21(34)11-15-4-3-5-18(10-15)35-25(26,27)28/h3-7,10,12-14H,2,8-9,11H2,1H3,(H2,29,30,31)
comment: Compound 22b represents a novel chemical scaffold class for receptor-interacting protein kinase 1 (RIPK1) inhibitors <Reference id=36553/>. It has shown anti-metastasis activity in the experimental B16 melanoma lung metastasis model. The molecular mechanism underlying this effect is identified as inhibition of tumour-dependent RIPK1-induced programmed necrosis (necroptosis) of vascular endothelial cells, which facilitates tumour cell extravasation and metastasis. Compound 22b is a type II kinase inhibitor that interacts with the inactive conformation (DFG-out) of the RIPK1 kinase domain.
iupac name: 1-(5-{4-Amino-7-ethyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl}-2,3-dihydro-1H-indol-1-yl)-2-[3-(trifluoromethoxy)phenyl]ethan-1-one
synonym: compound 22b [PMID: 30480444]
approved: f
ligand name: RIPK1 inhibitor 22b
type: SyntheticOrganicLigand

ML385
in ch i key: LINHYWKZVCNAMQ-UHFFFAOYSA-N
in ch i: InChI=1S/C29H25N3O4S/c1-17-5-3-4-6-22(17)28(34)32-12-11-20-15-21(8-9-23(20)32)27-18(2)37-29(31-27)30-26(33)14-19-7-10-24-25(13-19)36-16-35-24/h3-10,13,15H,11-12,14,16H2,1-2H3,(H,30,31,33)
comment: ML385 is a small molecule that binds to the Neh1 domain of the NRF2 transcription factor <Reference id=36541/>. Activating mutations in NRF2 (and loss-of-function (LOF) mutations in KEAP1, a protein that binds NRF2 and targets it for proteosomal degradation) have been reported to facilitate cytoprotective functions which are associated with mechanisms of chemotherapy resistance and tumour expansion in various solid tumour types <Reference id=36550/><Reference id=36545/><Reference id=36542/><Reference id=36543/><Reference id=36546/><Reference id=36547/>. Evidence from preclinical and clinical studies has validated Inhibition of NRF2 as a novel mechanistic therapeutic approach for treatment-resistant tumours <Reference id=36548/><Reference id=36549/>. ML385 inhibits NRF2 activity in non-small cell lung cancer (NSCLC) cells with LOF KEAP1 mutations in vitro and inhibits tumour growth in xenograft models using KEAP1 mutant NSCLC cells (in combination with <Ligand id=7624/>) <Reference id=36541/>.
iupac name: 2-(1,3-benzodioxol-5-yl)-N-[5-methyl-4-[1-(2-methylbenzoyl)-2,3-dihydroindol-5-yl]-1,3-thiazol-2-yl]acetamide
xref: CHEMBL1479098
synonym: ML-385
synonym: compound 2 [PMID: 27552339]
approved: f
ligand name: ML385
type: SyntheticOrganicLigand

halofuginone
in ch i key: LVASCWIMLIKXLA-UHFFFAOYSA-N
comment: Halofuginone is a synthetic derivative of febrifugine, a quinazolinone alkaloid first isolated from the roots of the blue evergreen hydrangea (D. febrifuga) and used as an antimalarial remedy in traditional Chinese medicine. The INN record for halofuginone indicates that it is a racemic mixture. We show the chemical structure without stereochemistry to represent the mixture. The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
iupac name: 7-bromo-6-chloro-3-[3-(3-hydroxypiperidin-2-yl)-2-oxopropyl]quinazolin-4-one
xref: CHEMBL1197091
approved: f
ligand name: halofuginone
type: SyntheticOrganicLigand

emavusertib
in ch i key: SJHNWSAWWOAWJH-MRXNPFEDSA-N
in ch i: InChI=1S/C24H25N7O5/c1-14-10-15(2-4-25-14)23-27-18(13-35-23)22(33)26-17-11-19-20(28-21(17)31-5-3-16(32)12-31)29-24(36-19)30-6-8-34-9-7-30/h2,4,10-11,13,16,32H,3,5-9,12H2,1H3,(H,26,33)/t16-/m1/s1
comment: CA-4948 is an orally available, reversible inhibitor of interleukin 1 receptor associated kinase 4 (IRAK4) <Reference id=41406/>. It downmodulates the IRAK4 activity that is required for Toll-like receptor (TLR) and interleukin-1 receptor (IL-1R) signalling in a variety of myeloid and lymphoid cell types, notably in cancer cells (e.g. diffuse large B-cell lymphoma cells) in which the MYD88 adaptor protein carries an activating mutation (MYD88L265P) <Reference id=36530/>. In such mutant cells NF-κB signaling is constitutively active and this is indicative of a poorer prognosis. Hence, IRAK4 inhibitors such as CA-4948 are expected to provide clinical benefit in MYD88 mutation +ve hematological cancers. The chemical structure of CA-4948 matches that submitted to the WHO for the INN emavusertib.
synonym: CA4948
synonym: AU-4948
synonym: AU4948
synonym: compound 24 [PMID: 33335659]
approved: f
ligand name: emavusertib
type: SyntheticOrganicLigand

vanillin
canonical SMILES: COc1cc(C=O)ccc1O
isomeric SMILES: COc1cc(C=O)ccc1O
in ch i key: MWOOGOJBHIARFG-UHFFFAOYSA-N
in ch i: InChI=1S/C8H8O3/c1-11-8-4-6(5-9)2-3-7(8)10/h2-5,10H,1H3
comment: Natural extract of the vanilla bean, now also available as a synthetic compound.
iupac name: 4-Hydroxy-3-methoxybenzaldehyde
xref: CHEMBL13883
synonym: vanilla
approved: f
ligand name: vanillin
type: NaturalProductLigand

K-604
in ch i key: VGGMTOYKEDKFLN-UHFFFAOYSA-N
in ch i: InChI=1S/C23H30N6OS3/c1-16-14-19(31-2)21(22(24-16)32-3)27-20(30)15-29-10-8-28(9-11-29)12-13-33-23-25-17-6-4-5-7-18(17)26-23/h4-7,14H,8-13,15H2,1-3H3,(H,25,26)(H,27,30)
comment: K-604 is a selective acetyl-CoA acetyltransferase 1 (ACAT1) inhibitor <Reference id=36526/> that is a clinical lead antihyperlipidemic agent <Reference id=36524/>. K-604 is also mentioned in patent US9149492B2 <Reference id=36525/>.
iupac name: 2-[4-[2-(1H-benzimidazol-2-ylsulfanyl)ethyl]piperazin-1-yl]-N-[6-methyl-2,4-bis(methylsulfanyl)pyridin-3-yl]acetamide
xref: CHEMBL3890942
synonym: compound 2 [PMID: 30433781]
synonym: K604
approved: f
ligand name: K-604
type: SyntheticOrganicLigand

SLC-0111
canonical SMILES: O=C(Nc1ccc(cc1)F)Nc1ccc(cc1)S(=O)(=O)N
isomeric SMILES: O=C(Nc1ccc(cc1)F)Nc1ccc(cc1)S(=O)(=O)N
in ch i key: YJQZNWPYLCNRLP-UHFFFAOYSA-N
in ch i: InChI=1S/C13H12FN3O3S/c14-9-1-3-10(4-2-9)16-13(18)17-11-5-7-12(8-6-11)21(15,19)20/h1-8H,(H2,15,19,20)(H2,16,17,18)
comment: SLC-0111 is a carbonic anhydrase (CA) IX/XII inhibitor that is being investigated for anti-neoplastic potential <Reference id=36518/><Reference id=36519/>. SLC-0111 is selective for the transmembrane CA isoforms IX and XII, compared to the cytosolic CA I and II isoforms. CA IX and XII are expressed predominantly in the hypoxic tumour microenvironment. Their inhibition promotes a significant antitumour/antimetastatic effect and reduces cancer stem cell numbers. The crystal structure of SLC-0111 bound to CA II has been resolved (see PDB ID 3N4B) <Reference id=36520/>.
iupac name: 1-(4-fluorophenyl)-3-(4-sulfamoylphenyl)urea
xref: CHEMBL1615281
synonym: 4-fluorophenylureido-benzenesulfonamide
synonym: SLC0111
synonym: compound 7 [PMID: 21361354]
approved: f
ligand name: SLC-0111
type: SyntheticOrganicLigand

JAK inhibitor 17b
in ch i key: RSFALMGMTQBFJZ-UHFFFAOYSA-N
in ch i: InChI=1S/C23H25N3O3/c1-28-19-10-16-17(11-20(19)29-2)23(27)26(13-14-6-4-3-5-7-14)21-15-8-9-24-22(15)25-12-18(16)21/h8-12,14H,3-7,13H2,1-2H3,(H,24,25)
comment: Inhibitor 17b represents a novel chemotype for Janus kinase inhibitors; benzo[ c]pyrrolo[2,3- h][1,6]naphthyridin-5-one (BPN) <Reference id=36442/>. It was identified using sequential palladium catalysis.
iupac name: 4-(Cyclohexylmethyl)-7,8-dimethoxy-1,4-dihydro-5H-benzo[c]pyrrolo[2,3-h][1,6]naphthyridin-5-one
approved: f
ligand name: JAK inhibitor 17b
type: SyntheticOrganicLigand

JAK inhibitor 20a
in ch i key: ZDNBWZRRFSXDFS-GOSISDBHSA-N
in ch i: InChI=1S/C24H23N5O4/c1-4-18(24(31)28-11-13(9-25)12-28)29-21-14-5-6-26-22(14)27-10-17(21)15-7-19(32-2)20(33-3)8-16(15)23(29)30/h5-8,10,13,18H,4,11-12H2,1-3H3,(H,26,27)/t18-/m1/s1
comment: Inhibitor 20a represents a novel chemotype for Janus kinase inhibitors; benzo[ c]pyrrolo[2,3- h][1,6]naphthyridin-5-one (BPN) <Reference id=36442/>. It was identified using sequential palladium catalysis.
iupac name: (R)-1-(2-(7,8-Dimethoxy-5-oxo-1,5-dihydro-4H-benzo[c]pyrrolo[2,3-h][1,6]naphthyridin-4-yl)butanoyl)azetidine-3-carbonitrile
approved: f
ligand name: JAK inhibitor 20a
type: SyntheticOrganicLigand

CXCR4 antagonist 22
in ch i key: XBEBHNXBLIDZDS-UHFFFAOYSA-N
in ch i: InChI=1S/C26H29ClN2/c27-26-12-5-4-10-25(26)20-29-15-13-21(14-16-29)18-28-19-22-7-6-11-24(17-22)23-8-2-1-3-9-23/h1-12,17,21,28H,13-16,18-20H2
comment: CXCR4 antagonist 22 is one of the most efficient compounds that was identified in a structure-based virtual screening and SAR optimisation study to find novel CXCR4 antagonists <Reference id=36441/>.
iupac name: 1-([1,1′-biphenyl]-3-yl)-N-((1-(2-chlorobenzyl)piperidin-4-yl)methyl)methanamine
approved: f
ligand name: CXCR4 antagonist 22
type: SyntheticOrganicLigand

SR1555
in ch i key: LTFVNEZXOPUABB-UHFFFAOYSA-N
in ch i: InChI=1S/C22H22F6N2O2/c1-15(31)30-12-10-29(11-13-30)14-16-2-4-17(5-3-16)18-6-8-19(9-7-18)20(32,21(23,24)25)22(26,27)28/h2-9,32H,10-14H2,1H3
comment: SR1555 is a selective inverse agonist of the retinoic acid-related orphan receptor γ (RORγ) <Reference id=36408/>.
iupac name: 1-[4-[[4-[4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)phenyl]phenyl]methyl]piperazin-1-yl]ethanone
xref: CHEMBL3218917
synonym: SR-1555
synonym: SR 1555
approved: f
ligand name: SR1555
type: SyntheticOrganicLigand

SR2211
in ch i key: KVHKWAZUPPBMLL-UHFFFAOYSA-N
in ch i: InChI=1S/C26H24F7N3O/c27-23-15-21(24(37,25(28,29)30)26(31,32)33)5-6-22(23)20-3-1-18(2-4-20)16-35-11-13-36(14-12-35)17-19-7-9-34-10-8-19/h1-10,15,37H,11-14,16-17H2
comment: SR2211 is a selective inverse agonist of the retinoic acid-related orphan receptor γ (RORγ) <Reference id=36409/>. It is a derivative of the RORα/γ inverse agonist <Ligand id=10143/>.
iupac name: 1,1,1,3,3,3-hexafluoro-2-[3-fluoro-4-[4-[[4-(pyridin-4-ylmethyl)piperazin-1-yl]methyl]phenyl]phenyl]propan-2-ol
xref: CHEMBL2137199
synonym: SR-2211
synonym: SR 2211
approved: f
ligand name: SR2211
type: SyntheticOrganicLigand

SR1001
in ch i key: OZBSSKGBKHOLGA-UHFFFAOYSA-N
comment: SR1001 is a synthetic retinoic-acid-receptor-related orphan receptor (ROR) modulator <Reference id=29073/>. Its interaction with the ligand binding sites of RORα and RORγt induces conformational changes in these receptors that alter co-activator/co-repressor binding affinity, and which lead to suppression of the receptors' transcriptional activity. Chemically SR1001 is a derivative of the liver X receptor ligand <Ligand id=2755/>, which has been shown to act as an inverse agonist of RORα and RORγ <Reference id=29072/>.
iupac name: N-[5-[[4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)phenyl]sulfamoyl]-4-methyl-1,3-thiazol-2-yl]acetamide
xref: CHEMBL3094388
synonym: SR-1001
synonym: SR 1001
approved: f
ligand name: SR1001
type: SyntheticOrganicLigand

PQR620
in ch i key: UGDKPWVVBKHRDK-UHFFFAOYSA-N
in ch i: InChI=1S/C21H25F2N7O2/c22-18(23)15-5-17(24)25-6-16(15)19-26-20(29-11-1-2-12(29)8-31-7-11)28-21(27-19)30-13-3-4-14(30)10-32-9-13/h5-6,11-14,18H,1-4,7-10H2,(H2,24,25)
comment: PQR620 is a potent and selective inhibitor of mTORC1/2 mTOR-containing complexes that was developed by PIQUR Therapeutics <Reference id=36400/>. It is brain-penetrating and is being analysed for clinical potential in neurological disorders and cancer. PQR620 was designed as a more effective alternative to the rapalogs <Ligand id=6031/>, <Ligand id=5889/> and <Ligand id=5892/> which show only modest overall response rates in solid tumours <Reference id=36401/>. Chemically PQR620 is a rationally designed derivative of <Ligand id=8383/> (PQR309), in which bimiralisib's trifluoromethyl group is substituted by a difluoromethyl group, and its morpholino groups are substituted with oxo-azabicyclo moieties.
iupac name: 5-[4,6-bis(3-oxa-8-azabicyclo[3.2.1]octan-8-yl)-1,3,5-triazin-2-yl]-4-(difluoromethyl)pyridin-2-amine
synonym: compound 3 [PMID: 30359003]
synonym: PQR-620
approved: f
ligand name: PQR620
type: SyntheticOrganicLigand

KDM5 inhibitor N71
in ch i key: KIIDGZQVWULCMZ-JXMROGBWSA-N
in ch i: InChI=1S/C28H34N4O4S/c1-31(2)13-7-10-25(33)30-21-9-6-8-20(18-21)26(36-17-16-32-14-4-3-5-15-32)24-19-23-27(37-24)22(28(34)35)11-12-29-23/h6-12,18-19,26H,3-5,13-17H2,1-2H3,(H,30,33)(H,34,35)/b10-7+
comment: N71 is a potent, selective and irreversible inhibitor of the protein lysine demethylases KDM5A and KDM5B <Reference id=36398/>. It was designed to interact and form a covalent bond with Cys481 of KDM5 enzymes which is a cysteine residue that is located near the enzymes' active site that is present in all 4 KDM5 family enzymes but not in other dioxygenases such as the KDM4 and KDM6 histone demethylases <Reference id=36399/>. KDM5A and KDM5B are known oncogenic drivers whose inhibition is of interest to those developing novel anti-cancer therapeutics.
approved: f
ligand name: KDM5 inhibitor N71
type: SyntheticOrganicLigand

STAT3 inhibitor 8q
in ch i key: MLNGLWWCXHUBMT-UHFFFAOYSA-N
in ch i: InChI=1S/C20H20N2O4/c23-17-13-6-2-3-7-14(13)18(24)19-15(17)12-16(26-19)20(25)21-8-11-22-9-4-1-5-10-22/h2-3,6-7,12H,1,4-5,8-11H2,(H,21,25)
comment: Compound 8q is reported as an orally active inhibitor of the transcription factor STAT3 <Reference id=36382/>. Structurally 8q is a derivative of <Ligand id=11358/> (BBI608), a cancer cell stemness inhibitor that targets the STAT3 pathway <Reference id=36386/>, and which was evaluated for antineoplastic potential in clinical trial <Reference id=36383/>. STAT3 is a crucial component of the JAK/STAT signalling pathway, that is implicated in cancer and inflammation. STAT3 is frequently activated in cancers, where it downmodulates intrinsic immune surveillance of tumour cells. Phosphorylated (activated) STAT3 (pSTAT3) is a marker of poor cancer prognosis <Reference id=36385/><Reference id=36384/>. Inhibition of the STA3 pathway induces T cell- and NK cell-dependent growth inhibition of tumours and by this mechanism, enhances antitumour immunity <Reference id=36387/>. Selective STAT3 inhibitors are being investigated as anti-cancer immunotherapeutics and as more general immunomodulators for non-cancer inflammatory disorders.
iupac name: 4,9-dioxo-N-[2-(piperidin-1-yl)ethyl]-4H,9H-naphtho[2,3-b]furan-2-carboxamide
approved: f
ligand name: STAT3 inhibitor 8q
type: SyntheticOrganicLigand

1R-11
isomeric SMILES: CCCCC[C@H](c1c(/C=C/[C@H]([C@H](CCCC(=O)OC)O)O)nc(n1C)C)O
in ch i key: PLBGFBROZZUTKG-PHCFSIKCSA-N
in ch i: InChI=1S/C20H34N2O5/c1-5-6-7-9-18(25)20-15(21-14(2)22(20)3)12-13-17(24)16(23)10-8-11-19(26)27-4/h12-13,16-18,23-25H,5-11H2,1-4H3/b13-12+/t16-,17+,18+/m0/s1
comment: 1R-11 is a synthetic lipoxin mimetic that exhibits anti-inflammatory activities via a mechanism which appears to be mediated by agonism of the ALX/FPR2 G protein-coupled receptor <Reference id=36381/>.
iupac name: methyl (E,5S,6R)-5,6-dihydroxy-8-[5-[(1R)-1-hydroxyhexyl]-1,2-dimethylimidazol-4-yl]oct-7-enoate
approved: f
ligand name: 1R-11
type: SyntheticOrganicLigand

YH18968
in ch i key: READJNFYOAOOFN-NRFANRHFSA-N
in ch i: InChI=1S/C27H28FN9O3/c1-17(2)25-32-26(33-40-25)35-8-6-34(7-9-35)24-19(13-29)11-20(14-30-24)18-3-4-23(22(28)12-18)36-16-31-37(27(36)38)21-5-10-39-15-21/h3-4,11-12,14,16-17,21H,5-10,15H2,1-2H3/t21-/m0/s1
comment: YH18968 is a GPR119 agonist that was developed as a potential therapeutic for treatment of type 2 diabetes mellitus <Reference id=36379/>. In rodent models it improves glucose tolerance, increases GLP-1 levels and augments the glucose lowering effects of a DPP4 inhibitor. It is one of the triazolone derivative compounds claimed in Yuhan Corporation's patent WO2014175621A1 <Reference id=36380/>.
iupac name: 5-[3-fluoro-4-[5-oxo-1-[(3S)-oxolan-3-yl]-1,2,4-triazol-4-yl]phenyl]-2-[4-(5-propan-2-yl-1,2,4-oxadiazol-3-yl)piperazin-1-yl]pyridine-3-carbonitrile
synonym: YH-18968
synonym: YH 18968
approved: f
ligand name: YH18968
type: SyntheticOrganicLigand

lazertinib
in ch i key: RRMJMHOQSALEJJ-UHFFFAOYSA-N
in ch i: InChI=1S/C30H34N8O3/c1-5-28(39)32-23-17-24(26(40-4)18-25(23)37-13-15-41-16-14-37)33-30-31-12-11-27(34-30)38-20-22(19-36(2)3)29(35-38)21-9-7-6-8-10-21/h5-12,17-18,20H,1,13-16,19H2,2-4H3,(H,32,39)(H,31,33,34)
comment: Lazertinib (YH-25448, GNS-1480) is an oral, third-generation inhibitor of the aberrant activity of mutant EGFR kinases (EGFR T790M and the activating EGFR mutations Ex19del and L858R), that was originally developed by Yuhan Corporation for antineoplastic potential in cancers with (acquired) resistance to existing EGFR tyrosine kinase inhibitors <Reference id=36378/>, in particular for EGFR mutation positive, advanced non-small cell lung cancer (NSCLC). It is claimed in Yuhan's patent WO2016060443A2 as compound 73 <Reference id=36378/>. In addition to predicted efficacy for the treatment of primary lung and extracranial lesions, lazertinib is expected to be beneficial for NSCLC brain metastases as it is able to cross the blood brain barrier.
iupac name: N-[5-[[4-[4-[(dimethylamino)methyl]-3-phenylpyrazol-1-yl]pyrimidin-2-yl]amino]-4-methoxy-2-morpholin-4-ylphenyl]prop-2-enamide
synonym: YH-25448
synonym: YH25448
synonym: GNS-1480
synonym: GNS1480
synonym: Compound 73 [WO2016060443A2]
synonym: Leclaza®
approved: t
ligand name: lazertinib
type: SyntheticOrganicLigand

VU2957
in ch i key: RUEXKBWCUUFJMY-UHFFFAOYSA-N
in ch i: InChI=1S/C16H10F3N5/c17-16(18,19)13-11-4-3-10(8-9(11)5-7-20-13)22-15-12-2-1-6-21-14(12)23-24-15/h1-8H,(H2,21,22,23,24)
comment: VU2957 is a potent, selective and orally active positive allosteric modulator of the metabotropic glutamate receptor subtype 4 (mGlu4) <Reference id=36377/>. It can cross the blood-brain barrier and has been evaluated as a preclinical candidate for the treatment of Parkinson's disease. Although it is active in vivo, the compound does not have the most conducive solubility. Selective activation of mGlu4 reduces motor symptoms in preclinical models of Parkinson's disease, primarily by decreasing the output of the indirect pathway in the basal ganglia.
iupac name: N-(2H-pyrazolo[3,4-b]pyridin-3-yl)-1-(trifluoromethyl)isoquinolin-6-amine
synonym: valiglurax
synonym: VU0652957
synonym: compound 7 (Panarese et al., 2018)
approved: f
ligand name: VU2957
type: SyntheticOrganicLigand

L-glutamine
canonical SMILES: NC(=O)CCC(C(=O)O)N
isomeric SMILES: NC(=O)CC[C@@H](C(=O)O)N
in ch i key: ZDXPYRJPNDTMRX-VKHMYHEASA-N
in ch i: InChI=1S/C5H10N2O3/c6-3(5(9)10)1-2-4(7)8/h3H,1-2,6H2,(H2,7,8)(H,9,10)/t3-/m0/s1
iupac name: (2S)-2,5-diamino-5-oxopentanoic acid
xref: CHEMBL930
synonym: Cebrogen
synonym: Earthlink Science Glutamine Chews Chocolate
synonym: Glavamin
synonym: Glutamine Express
synonym: Glutamine Fuel Mega
synonym: Glutamine Fuel Powder
synonym: L-Glutamine Power
synonym: Saforis
synonym: Stimulina
approved: f
ligand name: L-glutamine
type: MetaboliteLigand

IKK-beta inhibitor R-28
in ch i key: YGYGASJNJTYNOL-CQSZACIVSA-N
in ch i: InChI=1S/C22H23FN2O3S/c1-22(2)11-14(7-8-29(22,27)28)19-12-25-20-17(19)9-15(10-18(20)21(24)26)13-3-5-16(23)6-4-13/h3-6,9-10,12,14,25H,7-8,11H2,1-2H3,(H2,24,26)/t14-/m1/s1
comment: Inhibitor R-28 was designed as a pharmacological tool suitable for examining the function of IKKβ its role in disease pathogenesis, and the effects (good and bad) of inhibiting this kinase on immune function <Reference id=36373/>. It has favourable pharmacokinetics and in vivo activity. The chemical structure has been claimed in patents granted to GlaxoSmithKline (e.g. the most recent incarnation US8372875B2 <Reference id=36374/>).
iupac name: 3-[(4R)-2,2-dimethyl-1,1-dioxothian-4-yl]-5-(4-fluorophenyl)-1H-indole-7-carboxamide
synonym: example 225 [US8372875B2]
synonym: (R)-28
approved: f
ligand name: IKK-beta inhibitor R-28
type: SyntheticOrganicLigand

compound 27 [PMID: 24900635]
in ch i key: KNDPXYAMINMLED-UHFFFAOYSA-N
in ch i: InChI=1S/C20H13F4N5O2/c21-14-6-3-11(20(22,23)24)7-15(14)29-19(30)28-12-4-1-10(2-5-12)13-8-31-18-16(13)17(25)26-9-27-18/h1-9H,(H2,25,26,27)(H2,28,29,30)
comment: Compound 27 is a potent inhibitor of receptor interacting serine/threonine kinase 1 (RIPK1) <Reference id=26995/>. It is a type II inhibitor that is active against the DLG-out inactive conformation of the enzyme.
iupac name: 1-[4-(4-aminofuro[2,3-d]pyrimidin-5-yl)phenyl]-3-[2-fluoro-5-(trifluoromethyl)phenyl]urea
xref: CHEMBL247228
approved: f
ligand name: compound 27 [PMID: 24900635]
type: SyntheticOrganicLigand

GSK963
canonical SMILES: O=C(C(C)(C)C)N1N=CCC1c1ccccc1
isomeric SMILES: O=C(C(C)(C)C)N1N=CC[C@H]1c1ccccc1
in ch i key: NJQVSLWJBLPTMD-LBPRGKRZSA-N
in ch i: InChI=1S/C14H18N2O/c1-14(2,3)13(17)16-12(9-10-15-16)11-7-5-4-6-8-11/h4-8,10,12H,9H2,1-3H3/t12-/m0/s1
comment: GSK963 is a potent inhibitor of receptor interacting serine/threonine kinase 1 (RIPK1) <Reference id=36370/> that is suitable as a tool compound to study the function of RIPK1 in vitro and in vivo and to explore its contribution to inflammatory disease pathogenesis. GSK963 is the S enantiomer. The R enantiomer (GSK962) is inactive and can be used as a negative control to confirm on-target effects.
iupac name: 2,2-dimethyl-1-[(3S)-3-phenyl-3,4-dihydropyrazol-2-yl]propan-1-one
synonym: GSK'963
synonym: GSK′963A
approved: f
ligand name: GSK963
type: SyntheticOrganicLigand

UNC4203
in ch i key: HYUGTGGDEAGXJP-HRNNMHKYSA-N
in ch i: InChI=1S/C30H44N6O/c1-4-6-22(2)32-30-31-19-27-28(21-36(29(27)33-30)25-11-13-26(37)14-12-25)24-9-7-23(8-10-24)20-35-16-5-15-34(3)17-18-35/h7-10,19,21-22,25-26,37H,4-6,11-18,20H2,1-3H3,(H,31,32,33)/t22-,25-,26-/m0/s1
comment: The structure and activity of UNC4203 is disclosed in Zhao et al. (2018) <Reference id=36366/> and we rendered the structure using the SMILES string provided therein. It is one of the chemical structures claimed in patent US20150291606A1 <Reference id=36369/>, with therapeutic uses of such compounds claimed in WO2015157125A1 <Reference id=36367/>.
iupac name: trans-4-(5-(4-((4-Methyl-1,4-diazepan-1-yl)methyl)phenyl)-2-(((S)-pentan-2-yl)amino)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)cyclohexan-1-ol
synonym: MERTK inhibitor 19 [PMID: 30347155]
synonym: UNC4203A [US20150291606A1]
approved: f
ligand name: UNC4203
type: SyntheticOrganicLigand

SPRi3
canonical SMILES: COCC(=O)NCCc1c(C)[nH]c2c1cc(O)cc2
isomeric SMILES: COCC(=O)NCCc1c(C)[nH]c2c1cc(O)cc2
in ch i key: YBXBWBBVLXZQBJ-UHFFFAOYSA-N
in ch i: InChI=1S/C14H18N2O3/c1-9-11(5-6-15-14(18)8-19-2)12-7-10(17)3-4-13(12)16-9/h3-4,7,16-17H,5-6,8H2,1-2H3,(H,15,18)
comment: SPRi3 is a potent small-molecule inhibitor of sepiapterin reductase <Reference id=36354/><Reference id=36353/>, which is the terminal enzyme in the synthetic pathway for the metabolite and enzyme co-factor BH4 (also known as <Ligand id=5276/>). Structurally SPRi3 is a N-acetylserotonin analogue. It is one of the chemical structures (example 23) claimed in patent WO2011047156A1 <Reference id=36355/>.
iupac name: N-[2-(5-hydroxy-2-methyl-1H-indol-3-yl)ethyl]-2-methoxyacetamide
xref: CHEMBL3948731
synonym: SPR inhibitor 3
synonym: example 23 [WO2011047156]
approved: f
ligand name: SPRi3
type: SyntheticOrganicLigand

revefenacin
in ch i key: FYDWDCIFZSGNBU-UHFFFAOYSA-N
in ch i: InChI=1S/C35H43N5O4/c1-38(34(42)29-13-11-26(12-14-29)25-40-19-15-28(16-20-40)33(36)41)23-24-39-21-17-30(18-22-39)44-35(43)37-32-10-6-5-9-31(32)27-7-3-2-4-8-27/h2-14,28,30H,15-25H2,1H3,(H2,36,41)(H,37,43)
comment: Revefenacin (TD-4208) is a potent and long-acting muscarinic cholinergic receptor (mAChR) antagonist (LAMA) that has bronchodilatory effects <Reference id=36349/><Reference id=36350/>, and which is approved for the management of chronic obstructive pulmonary disease (COPD). mAChR antagonists are the core agents used as first-line therapy for COPD. Revefenacin acts as a competitive antagonist at all 5 human mAChRs <Reference id=36350/>.
iupac name: [1-[2-[[4-[(4-carbamoylpiperidin-1-yl)methyl]benzoyl]-methylamino]ethyl]piperidin-4-yl] N-(2-phenylphenyl)carbamate
xref: CHEMBL3833319
synonym: TD4208
synonym: Yupelri®
synonym: GSK1160724
synonym: GSK-1160724
approved: t
ligand name: revefenacin
type: SyntheticOrganicLigand

STING agonist 3
in ch i key: JGLMVXWAHNTPRF-CMDGGOBGSA-N
in ch i: InChI=1S/C42H51N13O7/c1-6-54-31(19-25(3)49-54)39(58)47-41-45-29-21-27(37(43)56)23-33(60-5)35(29)52(41)12-8-9-13-53-36-30(46-42(53)48-40(59)32-20-26(4)50-55(32)7-2)22-28(38(44)57)24-34(36)62-16-10-11-51-14-17-61-18-15-51/h8-9,19-24H,6-7,10-18H2,1-5H3,(H2,43,56)(H2,44,57)(H,45,47,58)(H,46,48,59)/b9-8+
comment: This compound is an optimised derivative of <Ligand id=10127/> that has improved solubility and improved potency in primary cells <Reference id=36347/>. Like agonist 2 it is one of the chemical structures claimed in GlaxoSmithKline's patent WO2017175147A1 <Reference id=36348/>. it behaves as a cyclic dinucleotide mimic to activate the STING pathway. SARS-CoV-2: Preclinical experimental evidence (in mice) suggests that this STING agonist may be effective in controlling infection by a range of SARS-CoV-2 variants, including B.1.351 (the beta variant <Reference id=42163/>) <Reference id=42162/>. The mechanistic hypothesis is that directly activating STING transiently stimulates interferon (IFN) signalling and circumvents the virus' ability to block IFN activation in infected respiratory epithelial cells, and re-establishes the innate immune response to infection.
iupac name: 1-[(2E)-4-[5-carbamoyl-2-(1-ethyl-3-methyl-1H-pyrazole-5-amido)-7-[3-(morpholin-4-yl)propoxy]-1H-1,3-benzodiazol-1-yl]but-2-en-1-yl]-2-(1-ethyl-3-methyl-1H-pyrazole-5-amido)-7-methoxy-1H-1,3-benzodiazole-5-carboxamide
synonym: diABZI
synonym: diABZI STING agonist-1
synonym: compound 3 [PMID: 30405246]
approved: f
ligand name: STING agonist 3
type: SyntheticOrganicLigand

STING agonist 2
in ch i key: ICZSAXDKFXTSGL-UHFFFAOYSA-N
in ch i: InChI=1S/C34H38N12O4/c1-5-45-27(15-19(3)41-45)31(49)39-33-37-23-17-21(29(35)47)9-11-25(23)43(33)13-7-8-14-44-26-12-10-22(30(36)48)18-24(26)38-34(44)40-32(50)28-16-20(4)42-46(28)6-2/h9-12,15-18H,5-8,13-14H2,1-4H3,(H2,35,47)(H2,36,48)(H,37,39,49)(H,38,40,50)
comment: This compound is a potent agonist of the stimulator of interferon genes (STING) protein, which is an intracellular detector/receptor of pathogen-derived and self DNA in the cytosol <Reference id=36347/>. It was designed to be a systemically active immune-modifying anti-cancer therapeutic, with the potential to outperfom existing modified cyclic dinucleotide-based cGAMP (the endogenous STING agonist) development compounds, which are generally active by intratumoral delivery in a restricted range of accessible tumours. It is one of the chemical structures claimed in GlaxoSmithKline's patent WO2017175147A1 <Reference id=36348/>.
iupac name: 1-{4-[5-carbamoyl-2-(1-ethyl-3-methyl-1H-pyrazole-5-amido)-1H-1,3-benzodiazol-1-yl]butyl}-2-(1-ethyl-3-methyl-1H-pyrazole-5-amido)-1H-1,3-benzodiazole-5-carboxamide
approved: f
ligand name: STING agonist 2
type: SyntheticOrganicLigand

tryptanthrin 5i
in ch i key: UFMQJYHLIUACCG-UHFFFAOYSA-N
in ch i: InChI=1S/C15H7N3O4/c19-13-10-7-8(18(21)22)5-6-12(10)17-14(13)16-11-4-2-1-3-9(11)15(17)20/h1-7H
comment: Compound 5i is a <Ligand id=8224/> analogue that acts as an inhibitor of indoleamine 2, 3-dioxygenase (IDO) 1 and IDO2 <Reference id=27057/><Reference id=36340/>. It is a non-competitive inhibitor of IDO2.
xref: CHEMBL432537
synonym: compound 5i [PMID: 24099220]
approved: f
ligand name: tryptanthrin 5i
type: SyntheticOrganicLigand

PFKFB3 kinase Inhibitor 69
in ch i key: CYJRNFFLTBEQSQ-UHFFFAOYSA-N
in ch i: InChI=1S/C23H18N4O2S2/c1-14-13-30-21-4-3-15(9-17(14)21)18-10-16(11-19-23(18)26-8-7-25-19)27-20-12-24-6-5-22(20)31(2,28)29/h3-13,27H,1-2H3
comment: PFKFB3 kinase Inhibitor 69 is the most potent of a series of compounds designed by Boutard et al. (2018) for potential anti-cancer activity <Reference id=36338/>. It is one of the chemical structures claimed in patent WO2016180537A1, namely Example 110 <Reference id=36339/>. 6-phosphofructo-2-kinase/fructose-2,6-biphosphatase 3 (PFKFB3) is the ubiquitously expressed and hypoxia-induced isoform of PFK-2, which is an enzyme that catalyses the production of fructose-2,6-bisphosphate, a metabolite that drives aerobic glycolysis and energy production in cancer cells.
iupac name: N-(4-methanesulfonylpyridin-3-yl)-8-(3-methyl-1-benzothiophen-5-yl)quinoxalin-6-amine
synonym: example 110 [WO2016180537]
synonym: compound 69 [PMID: 30378281]
approved: f
ligand name: PFKFB3 kinase Inhibitor 69
type: SyntheticOrganicLigand

dual sEH/FAAH inhibitor 11
in ch i key: LWLSVNFEVKJDBZ-UHFFFAOYSA-N
in ch i: InChI=1S/C26H23F6N3O3/c27-25(28,29)19-4-9-23(33-16-19)37-22-3-1-2-18(15-22)14-17-10-12-35(13-11-17)24(36)34-20-5-7-21(8-6-20)38-26(30,31)32/h1-9,15-17H,10-14H2,(H,34,36)
comment: Inhibitor 11 was designed as a dual inhibitor of fatty acid amide hydrolase (FAAH) and soluble epoxide hydrolase (sEH), two enzymes that independently down-modulate inflammatory and neuropathic pain <Reference id=36336/>. The structure-activity relationship exploration was initiated using the potent FAAH inhibitor <Ligand id=5244/> (which is a weak sEH inhibitor). Inhibitor 11 is one of the chemical structures claimed in patent WO2017160861A1, specifically example 28 (B-11) <Reference id=36337/>. Inhibitor 11 exhibits favourable target selectivity, pharmacokinetic properties and in vivo target engagement <Reference id=36336/>.
iupac name: N-[4-(trifluoromethoxy)phenyl]-4-[(3-{[5-(trifluoromethyl)pyridin-2-yl]oxy}phenyl)methyl]piperidine-1-carboxamide
synonym: compound B-11 [WO2017160861]
synonym: example 28 [WO2017160861]
approved: f
ligand name: dual sEH/FAAH inhibitor 11
type: SyntheticOrganicLigand

MDL-800
in ch i key: FKFQBYBODAKGOA-UHFFFAOYSA-N
comment: MDL-800 is an allosteric activator of SIRT6 that is active in vitro and in physiological experiments (e.g. tumour xenograft models) <Reference id=36327/>. It increases the deacetylase activity of SIRT6 which leads to decreased H3K9 and H3K56 acetyl-lysine marks in cancer cells in vitro and an anti-tumour effect.
iupac name: methyl 2-[(5-bromo-4-fluoro-2-methylphenyl)sulfamoyl]-5-(3,5-dichlorobenzenesulfonamido)benzoate
approved: f
ligand name: MDL-800
type: SyntheticOrganicLigand

H-151
canonical SMILES: CCc1ccc(cc1)NC(=O)Nc1c[nH]c2c1cccc2
isomeric SMILES: CCc1ccc(cc1)NC(=O)Nc1c[nH]c2c1cccc2
in ch i key: UJZDIKVQFMCLBE-UHFFFAOYSA-N
in ch i: InChI=1S/C17H17N3O/c1-2-12-7-9-13(10-8-12)19-17(21)20-16-11-18-15-6-4-3-5-14(15)16/h3-11,18H,2H2,1H3,(H2,19,20,21)
comment: H-151 is a small molecule covalent STING antagonist <Reference id=36325/>. Mechanistically it binds to Cys91 of the protein and prevents its palmitoylation. The non-modified STING protein is then unable to assemble the STING complexes that are essential to activate downstream processes (e.g. Type I interferon response). H-151 has been reported to reduce SARS-CoV-2-induced lung inflammation and to improve disease outcome in ACE2-humanised mice <Reference id=43293/>.
iupac name: 3-(4-ethylphenyl)-1-(1H-indol-3-yl)urea
synonym: H151
synonym: H 151
approved: f
ligand name: H-151
type: SyntheticOrganicLigand

F215
canonical SMILES: Clc1cccc(c1)CCCCCC(=O)N1CCOC1=O
isomeric SMILES: Clc1cccc(c1)CCCCCC(=O)N1CCOC1=O
in ch i key: XNQIFNVZSXXYRQ-UHFFFAOYSA-N
in ch i: InChI=1S/C15H18ClNO3/c16-13-7-4-6-12(11-13)5-2-1-3-8-14(18)17-9-10-20-15(17)19/h4,6-7,11H,1-3,5,8-10H2
comment: F215 is an inhibitor of N-Acylethanolamine acid amidase (NAAA) <Reference id=36318/>. It was designed for anti-inflammatory potential.
iupac name: 3-[6-(3-chlorophenyl)hexanoyl]-1,3-oxazolidin-2-one
approved: f
ligand name: F215
type: SyntheticOrganicLigand

ARN19702
in ch i key: UKQOLPNYRVPCBM-AWEZNQCLSA-N
comment: ARN19702 is a second generation non-covalent inhibitor of N-acylethanolamine acid amidase (NAAA) <Reference id=32616/>.
iupac name: (2-ethylsulfonylphenyl)-[(2S)-4-(6-fluoro-1,3-benzothiazol-2-yl)-2-methyl-piperazin-1-yl]methanone
synonym: compound 8 [PMID: 27404798]
synonym: ARN-19702
approved: f
ligand name: ARN19702
type: SyntheticOrganicLigand

Grp94 inhibitor 54
in ch i key: JMGDXIHGWTVBMX-WGSAOQKQSA-N
in ch i: InChI=1S/C22H28N2O2/c1-14(2)15-3-5-16(6-4-15)17-7-12-21(20(13-17)22(23)26)24-18-8-10-19(25)11-9-18/h3-7,12-14,18-19,24-25H,8-11H2,1-2H3,(H2,23,26)/t18-,19-
comment: This compound is a selective inhibitor of the endoplasmic reticulum chaperone protein GRP94 <Reference id=36311/>. It has demonstrated anti-inflammatory efficacy in the mouse DSS-induced model of ulcerative colitis.
iupac name: 4'-(propan-2-yl)-4-{[(1r,4r)-4-hydroxycyclohexyl]amino}-[1,1'-biphenyl]-3-carboxamide
approved: f
ligand name: Grp94 inhibitor 54
type: SyntheticOrganicLigand

AUNP-12
in ch i key: YQYGGOPUTPQHAY-KIQLFZLRSA-N
comment: AUNP-12 is a small branched peptide inhibitor of the PD-1/PD-L1 pathway that was developed by Aurigene Discovery Technologies and is claimed in their patent WO2011161699A3 <Reference id=36298/>. It interacts with PD-1 and prevents binding of both PD-L1 and PD-L2 <Reference id=36299/>. It is composed of two linked peptide chains (sequence 1 SNTSESFKFRVTQLAPKAQIKE and sequence 2 SNTSESF), with a total of 29 amino acids. Peptidic antagonists of PD-1 binding by PD-L1/L2 such as AUNP-12 are being developed with the aim of overcoming the pharmacokinetic, manufacture and useage limitations of the current monoclonal antibody PD-1 pathway inhibitors, as well as reducing some of their severe immune-related adverse events <Reference id=33409/>.
synonym: Aurigene NP-12
synonym: Aurigene-012
synonym: Aur-012
synonym: compound #8 [WO2011161699A3]
approved: f
ligand name: AUNP-12
type: PeptideLigand

S5A1
in ch i key: WERPJWHERZIQSB-UHFFFAOYSA-N
in ch i: InChI=1S/C27H33N3O4/c1-3-34-24-15-21(23(14-18(24)2)19-4-5-19)16-29-12-10-27(11-13-29)17-30(26(33)28-27)22-8-6-20(7-9-22)25(31)32/h6-9,14-15,19H,3-5,10-13,16-17H2,1-2H3,(H,28,33)(H,31,32)
comment: Selective SST5 receptor antagonist.
iupac name: 4-[8-[(2-cyclopropyl-5-ethoxy-4-methylphenyl)methyl]-2-oxo-1,3,8-triazaspiro[4.5]decan-3-yl]benzoic acid
approved: f
ligand name: S5A1
type: SyntheticOrganicLigand

J-2156
in ch i key: VTNCZBXJSGKDLS-SFTDATJTSA-N
in ch i: InChI=1S/C24H28N4O4S/c1-16-11-12-22(19-10-6-5-9-18(16)19)33(31,32)28-20(13-14-25)24(30)27-21(23(26)29)15-17-7-3-2-4-8-17/h2-12,20-21,28H,13-15,25H2,1H3,(H2,26,29)(H,27,30)/t20-,21-/m0/s1
comment: Selective SST4 receptor agonist.
iupac name: (2S)-4-amino-N-[(2S)-1-amino-1-oxo-3-phenylpropan-2-yl]-2-[(4-methylnaphthalen-1-yl)sulfonylamino]butanamide
synonym: J2156
synonym: J 2156
approved: f
ligand name: J-2156
type: SyntheticOrganicLigand

MK-4256
in ch i key: NTIFDLOQPKMIJK-AJTFRIOCSA-N
in ch i: InChI=1S/C27H23FN8O/c1-15-31-26(35-37-15)27(17-12-30-36(2)14-17)24-20(19-5-3-4-6-21(19)32-24)11-22(34-27)25-29-13-23(33-25)16-7-9-18(28)10-8-16/h3-10,12-14,22,32,34H,11H2,1-2H3,(H,29,33)/t22-,27-/m1/s1
comment: MK-4256 is a potent and selective SST3 receptor antagonist.
iupac name: 3-[(1R,3R)-3-[5-(4-fluorophenyl)-1H-imidazol-2-yl]-1-(1-methylpyrazol-4-yl)-2,3,4,9-tetrahydropyrido[3,4-b]indol-1-yl]-5-methyl-1,2,4-oxadiazole
synonym: MK4256
synonym: MK 4256
approved: f
ligand name: MK-4256
type: SyntheticOrganicLigand

Dooku1
canonical SMILES: Clc1cccc(c1CSc1nnc(o1)c1[nH]ccc1)Cl
isomeric SMILES: Clc1cccc(c1CSc1nnc(o1)c1[nH]ccc1)Cl
in ch i key: MNPOBXLPCWFONX-UHFFFAOYSA-N
in ch i: InChI=1S/C13H9Cl2N3OS/c14-9-3-1-4-10(15)8(9)7-20-13-18-17-12(19-13)11-5-2-6-16-11/h1-6,16H,7H2
comment: Dooku 1 blocks <Ligand id=9817/>-induced activation of Piezo1 ion channels <Reference id=34405/>. It has no effect on constitutive Piezo1 activity.
iupac name: 2-[(2,6-Dichlorobenzyl)thio)-5-(1H-pyrrol-2-yl)-1,3,4-oxadiazole
synonym: Dooku-1
synonym: Dooku 1
approved: f
ligand name: Dooku1
type: SyntheticOrganicLigand

Jedi2
canonical SMILES: OC(=O)c1cc(oc1C)c1cccs1
isomeric SMILES: OC(=O)c1cc(oc1C)c1cccs1
in ch i key: YXDCRSXNEOKXDE-UHFFFAOYSA-N
in ch i: InChI=1S/C10H8O3S/c1-6-7(10(11)12)5-8(13-6)9-3-2-4-14-9/h2-5H,1H3,(H,11,12)
comment: Jedi2 is reported as an activator of the mechanosensitive Piezo1 ion channel <Reference id=36290/>.
iupac name: 2-methyl-5-thiophen-2-ylfuran-3-carboxylic acid
synonym: Jedi 2
synonym: Jedi-2
approved: f
ligand name: Jedi2
type: SyntheticOrganicLigand

PGN-9856
in ch i key: HZJWJNHYKNSGAT-UHFFFAOYSA-N
in ch i: InChI=1S/C21H15F2NO4/c22-15-4-1-3-13(9-15)14-7-8-19(23)18(10-14)21(27)24-16-5-2-6-17(11-16)28-12-20(25)26/h1-11H,12H2,(H,24,27)(H,25,26)
comment: Potent, selective, and efficacious prostanoid EP2 receptor agonist.
iupac name: 2-[3-[[2-fluoro-5-(3-fluorophenyl)benzoyl]amino]phenoxy]acetic acid
synonym: PGN9856
synonym: PGN 9856
approved: f
ligand name: PGN-9856
type: SyntheticOrganicLigand

7-BIA
canonical SMILES: CCCCOc1cc2C(=O)OC(Cc2c(c1OC)C=O)O
isomeric SMILES: CCCCOc1cc2C(=O)OC(Cc2c(c1OC)C=O)O
in ch i key: DAVCIYWSVYDJKW-UHFFFAOYSA-N
in ch i: InChI=1S/C15H18O6/c1-3-4-5-20-12-6-10-9(7-13(17)21-15(10)18)11(8-16)14(12)19-2/h6,8,13,17H,3-5,7H2,1-2H3
comment: 7-BIA is a 7-butoxy analogue of illudalic acid (PubChem CID 3653077) that has been reported as an inhibitor of receptor type protein tyrosine phosphatase D (PTPRD) <Reference id=36281/>, which is a novel therapeutic target for the treatment of addiction.
iupac name: 7-butoxy-3-hydroxy-6-methoxy-1-oxo-3,4-dihydro-1H-2-benzopyran-5-carbaldehyde
synonym: compound 14 [PMID: 30348770]
approved: f
ligand name: 7-BIA
type: SyntheticOrganicLigand

GSK2646264
in ch i key: CQLSAYKHANAIMX-UHFFFAOYSA-N
in ch i: InChI=1S/C24H28N2O2/c1-17-8-13-26-21(14-17)16-28-23-5-3-4-22(27-2)24(23)20-7-6-18-9-11-25-12-10-19(18)15-20/h3-8,13-15,18-19,25H,9-12,16H2,1-2H3
comment: GSK2646264 is a skin permeable Syk inhibitor that is being investigated as a topical treatment for skin inflammation <Reference id=36279/>. An X-ray crystal structure of GSK2646264 bound to human SYK reveals that it binds the enzyme's aspartate 512 residue which lies within the ribose pocket in the ATP binding site of Syk.
iupac name: 7-{2-methoxy-6-[(4-methylpyridin-2-yl)methoxy]phenyl}-2,3,4,5,5a,9a-hexahydro-1H-3-benzazepine
synonym: compound 44 [PMID: 30249354]
approved: f
ligand name: GSK2646264
type: SyntheticOrganicLigand

TUG-1375
in ch i key: RZAMDGBOOPJHJQ-NQIIRXRSSA-N
comment: TUG-1375 was designed as a selective free fatty acid receptor 2 (FFA2/GPR43) agonist, as a pharmacological tool that is suitable for the study of FFA2 receptor function in vitro and in vivo <Reference id=36272/>. FFA2 is known to be involved in regulation of metabolism, appetite, fat accumulation and inflammatory responses.
iupac name: (2R,4R)-2-(2-chlorophenyl)-3-(4-(3,5-dimethylisoxazol-4-yl)benzoyl)thiazolidine-4-carboxylic acid
synonym: TUG1375
synonym: compound 31 [PMID: 30247908]
approved: f
ligand name: TUG-1375
type: SyntheticOrganicLigand

CCR5 antagonist 34
in ch i key: KESMRFWRGXZDEF-KIHHCIJBSA-N
in ch i: InChI=1S/C27H39F2N5OS/c1-17(2)25-32-31-18(3)34(25)23-14-21-4-5-22(15-23)33(21)12-8-24(20-9-13-36-16-20)30-26(35)19-6-10-27(28,29)11-7-19/h9,13,16-17,19,21-24H,4-8,10-12,14-15H2,1-3H3,(H,30,35)/t21-,22+,23-,24-/m0/s1
comment: This CCR5 antagonist was designed to overcome some of the detrimental issues associated with the approved CCR5 antagonist <Ligand id=806/> (an HIV entry inhibitor drug;) such as CYP450 inhibition, hERG inhibition and viral resistance <Reference id=36270/>. It is one of the chemical structures claimed in patent WO2015101265A1 belonging to the Shanghai Institute of Materia Medica <Reference id=36271/>.
iupac name: 4,4-difluoro-N-[(1S)-3-[(1S,5R)-3-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octan-8-yl]-1-thiophen-3-ylpropyl]cyclohexane-1-carboxamide
approved: f
ligand name: CCR5 antagonist 34
type: SyntheticOrganicLigand

DDR1/2 inhibitor 5n
in ch i key: IUGBGEUCXVKGQK-UHFFFAOYSA-N
in ch i: InChI=1S/C31H31F3N6O/c1-21(2)28-7-5-24(16-23(28)4-6-27-18-36-29-19-35-8-9-40(27)29)30(41)37-26-15-22(14-25(17-26)31(32,33)34)20-39-12-10-38(3)11-13-39/h5,7-9,14-19,21H,10-13,20H2,1-3H3,(H,37,41)
comment: The DDR1 and DDR2 receptor tyrosine kinases are new potential targets for anti-inflammatory drug discovery, as they are critical mediators of inflammatory cytokine secretion whose dysregulation is implicated in the progression of various human inflammatory diseases, including fibrosis, arthritis, atherosclerosis and cancer <Reference id=36255/><Reference id=31276/>. The dual inhibitor compound 5n was designed to investigate the anti-inflammatory potential of coinhibiting these enzymes, and provides a lead scaffold for further optimisation <Reference id=36254/>.
iupac name: 3-(2-imidazo[1,2-a]pyrazin-3-ylethynyl)-N-[3-[(4-methylpiperazin-1-yl)methyl]-5-(trifluoromethyl)phenyl]-4-propan-2-ylbenzamide
approved: f
ligand name: DDR1/2 inhibitor 5n
type: SyntheticOrganicLigand

L-citrulline
canonical SMILES: NC(=O)NCCCC(C(=O)O)N
isomeric SMILES: NC(=O)NCCC[C@@H](C(=O)O)N
in ch i key: RHGKLRLOHDJJDR-BYPYZUCNSA-N
in ch i: InChI=1S/C6H13N3O3/c7-4(5(10)11)2-1-3-9-6(8)12/h4H,1-3,7H2,(H,10,11)(H3,8,9,12)/t4-/m0/s1
iupac name: (2S)-2-amino-5-(carbamoylamino)pentanoic acid
xref: CHEMBL444814
approved: f
ligand name: L-citrulline
type: SyntheticOrganicLigand

rupatadine
in ch i key: WUZYKBABMWJHDL-UHFFFAOYSA-N
in ch i: InChI=1S/C26H26ClN3/c1-18-13-19(16-28-15-18)17-30-11-8-20(9-12-30)25-24-7-6-23(27)14-22(24)5-4-21-3-2-10-29-26(21)25/h2-3,6-7,10,13-16H,4-5,8-9,11-12,17H2,1H3
comment: Rupatadine is a second generation histamine H1 receptor and platelet-activating factor (PAF) receptor antagonist <Reference id=36244/><Reference id=36247/>. It is selective, long-acting and non-sedating. It was designed as a single structure dual antagonist based on evidence that PAF appears to act alongside histamine in the pathogenesis of the allergic response.
iupac name: 8-chloro-11-[1-[(5-methylpyridin-3-yl)methyl]piperidin-4-ylidene]-5,6-dihydrobenzo[1,2]cyclohepta[2,4-b]pyridine
xref: CHEMBL91397
synonym: Rupafin®
synonym: Rinialer®
synonym: UR-12592
synonym: UR12592
approved: t
ligand name: rupatadine
type: SyntheticOrganicLigand

mizolastine
in ch i key: PVLJETXTTWAYEW-UHFFFAOYSA-N
in ch i: InChI=1S/C24H25FN6O/c1-29(23-26-13-10-22(32)28-23)19-11-14-30(15-12-19)24-27-20-4-2-3-5-21(20)31(24)16-17-6-8-18(25)9-7-17/h2-10,13,19H,11-12,14-16H2,1H3,(H,26,28,32)
comment: Mizolastine is a highly selective, long-acting second generation histamine H1 receptor antagonist <Reference id=36243/> that is used clinically as an antiallergy medication. It does not cross the blood-brain barrier and does not bind the muscarinic cholinergic M1 receptor <Reference id=36242/>.
xref: CHEMBL94454
synonym: MKC431
synonym: MKC-431
synonym: MKC 431
synonym: SL 850324
synonym: SL850324
synonym: SL-850324
synonym: Mizollen®
synonym: SL 85.0324
approved: t
ligand name: mizolastine
type: SyntheticOrganicLigand

dimetindene
canonical SMILES: CN(CCC1=C(C(c2ccccn2)C)c2c(C1)cccc2)C
isomeric SMILES: CN(CCC1=C(C(c2ccccn2)C)c2c(C1)cccc2)C
in ch i key: MVMQESMQSYOVGV-UHFFFAOYSA-N
in ch i: InChI=1S/C20H24N2/c1-15(19-10-6-7-12-21-19)20-17(11-13-22(2)3)14-16-8-4-5-9-18(16)20/h4-10,12,15H,11,13-14H2,1-3H3
comment: Dimetindene is an orally active, selective histamine H1 receptor antagonist. It also has anticholinergic activity <Reference id=36241/>. The INN specifies the racemic mixture of (R)- and (S)-enantiomers. We show the structure without specified stereochemistry to represent that mixture.
iupac name: N,N-dimethyl-2-[3-(1-pyridin-2-ylethyl)-1H-inden-2-yl]ethanamine
xref: CHEMBL22108
synonym: dimethindene
synonym: dimethpyrindene
synonym: (+/-)-dimethindene
synonym: Fenistil®
synonym: Vibrocil®
approved: t
ligand name: dimetindene
type: SyntheticOrganicLigand

vibegron
in ch i key: DJXRIQMCROIRCZ-XOEOCAAJSA-N
in ch i: InChI=1S/C26H28N4O3/c31-24-14-15-27-23-13-12-22(30(23)24)26(33)29-19-8-6-17(7-9-19)16-20-10-11-21(28-20)25(32)18-4-2-1-3-5-18/h1-9,14-15,20-22,25,28,32H,10-13,16H2,(H,29,33)/t20-,21+,22-,25+/m0/s1
comment: Vibegron (MK-4618) is a potent and selective β3 adrenoceptor agonist that was developed by Merck as a pharmacological modulator for the management of overactive bladder <Reference id=36239/><Reference id=36240/>.
xref: CHEMBL2107826
synonym: MK-4618
synonym: MK4618
synonym: KRP-114V
synonym: compound 7 [PMID: 26709102]
synonym: Gemtesa®
approved: t
ligand name: vibegron
type: SyntheticOrganicLigand

zifaxaban
in ch i key: MXWOUAQNXIUJIN-HNNXBMFYSA-N
comment: Zifaxaban is an orally active direct factor Xa inhibitor <Reference id=36238/>. There is one patent hit for this compound, WO2014183665A1 <Reference id=37678/>. Zifaxaban appears to be a 'pseudo' INN. It includes the INN stem for a factor Xa inhibitor (%22xaban%22), but has not (yet) been submitted to the World Health Organisation for ratification.
iupac name: 5-chloro-N-[[(5S)-2-oxo-3-[4-(2-oxopyridin-1-yl)phenyl]-1,3-oxazolidin-5-yl]methyl]thiophene-2-carboxamide
synonym: TY-602
synonym: TY602
approved: f
ligand name: zifaxaban
type: SyntheticOrganicLigand

parsaclisib
in ch i key: ZQPDJCIXJHUERQ-VUWPPUDQSA-N
comment: Parsaclisib (INCB050465) is a PI3Kδ inhibitor that was developed by Incyte Corporation as an antineoplastic and immunomodulatory agent, as claimed in their patent WO2014134426A1 <Reference id=36232/>. The chemical structure is one of those claimed in patent WO2013033569A1, but it was not immediately clear which example it was from a mixture of diastereoisomers 345-348 (347 and 348 had the highest inhibitory potency vs. PI3Kδ and 347 was tested in vivo) <Reference id=36233/>. The 2019 disclosure by Yue et al. confirmed the structure as patent example 346 <Reference id=39869/>. Preclinical and phase 1/2 clinical evidence suggests that compared to first-generation PI3Kδ inhibitors, parsaclisib has reduced hepatotoxicity <Reference id=39868/>.
synonym: INCB-050465
synonym: compound 20 [PMID: 31749910]
synonym: IBI376
approved: f
ligand name: parsaclisib
type: SyntheticOrganicLigand

paxalisib
in ch i key: LGWACEZVCMBSKW-UHFFFAOYSA-N
in ch i: InChI=1S/C18H22N8O2/c1-18(2)16-22-12-14(25-3-6-27-7-4-25)23-13(11-9-20-17(19)21-10-11)24-15(12)26(16)5-8-28-18/h9-10H,3-8H2,1-2H3,(H2,19,20,21)
comment: Paxalisib (GDC0084) is a dual PI3K/mTOR inhibitor that was developed by Genentech <Reference id=36231/>. It was designed to cross the blood-brain-barrier as a potential oncology drug for the treatment of malignant gliomas.
iupac name: 5-(6,6-dimethyl-4-morpholin-4-yl-8,9-dihydropurino[8,9-c][1,4]oxazin-2-yl)pyrimidin-2-amine
xref: CHEMBL3813842
synonym: GDC0084
synonym: GDC-0084
synonym: GDC 0084
synonym: compound 16 [PMID: 27096040]
approved: f
ligand name: paxalisib
type: SyntheticOrganicLigand

acalisib
in ch i key: DOCINCLJNAXZQF-LBPRGKRZSA-N
in ch i: InChI=1S/C21H16FN7O/c1-12(27-19-17-18(24-10-23-17)25-11-26-19)20-28-16-8-7-13(22)9-15(16)21(30)29(20)14-5-3-2-4-6-14/h2-12H,1H3,(H2,23,24,25,26,27)/t12-/m0/s1
comment: Acalisib (GS9820) is a PI3Kδ inhibitor <Reference id=36230/> that is being investigated for anti-neoplastic and immunomodulatory potential.
iupac name: 6-fluoro-3-phenyl-2-[(1S)-1-(7H-purin-6-ylamino)ethyl]quinazolin-4-one
synonym: GS-9820
synonym: GS 9820
synonym: CAL-120
approved: f
ligand name: acalisib
type: SyntheticOrganicLigand

RO3306
canonical SMILES: O=C1N=C(SC1=Cc1ccc2c(c1)cccn2)NCc1cccs1
isomeric SMILES: O=C1N=C(SC1=Cc1ccc2c(c1)cccn2)NCc1cccs1
in ch i key: XOLMRFUGOINFDQ-UHFFFAOYSA-N
in ch i: InChI=1S/C18H13N3OS2/c22-17-16(24-18(21-17)20-11-14-4-2-8-23-14)10-12-5-6-15-13(9-12)3-1-7-19-15/h1-10H,11H2,(H,20,21,22)
comment: The selectivity profile of RO3306 (structure reported in <Reference id=36226/>) suggests that is the most suitable CDK1 chemical probe to be reported (as of October 2018) <Reference id=36225/>. Additional non-CDK off-targets that should be considered when interpreting experimental results include PKCδ (Ki 318 nM), SGK (Ki 497 nM) and ERK (Ki 1980 nM) <Reference id=36226/>.
synonym: RO-3306
synonym: RO 3306
approved: f
ligand name: RO3306
type: SyntheticOrganicLigand

BTK inhibitor 4b
in ch i key: RQYDQAPLARKISN-UHFFFAOYSA-N
in ch i: InChI=1S/C26H23FN8O2/c1-34-12-17(11-29-34)30-26-32-23(31-25(28)33-26)18-3-2-4-21(19(18)13-36)35-8-7-15-9-16(14-5-6-14)10-20(27)22(15)24(35)37/h2-4,7-12,14,36H,5-6,13H2,1H3,(H3,28,30,31,32,33)
comment: This compound is reported as a selective inhbitor of Bruton's tyrosine kinase (BTK) <Reference id=36221/>. Compared to existing BTK inhibitors it has a novel aminotriazine scaffold. Inhibitor 4b has been advanced to preclinical studies for evaluation of its anti-inflammatory potential. This is one of the chemical structures claimed in Carna Bioscience's patent WO2015012149A1 <Reference id=36222/>.
iupac name: 2-(3-{4-Amino-6-[(1-methyl-1H-pyrazol-4-yl)amino]-1,3,5-triazin-2-yl}-2-(hydroxymethyl)phenyl)-6-cyclopropyl-8-fluoroisoquinolin-1(2H)-one
synonym: compound 4b [PMID: 30216722]
approved: f
ligand name: BTK inhibitor 4b
type: SyntheticOrganicLigand

modafinil
canonical SMILES: NC(=O)CS(=O)C(c1ccccc1)c1ccccc1
isomeric SMILES: NC(=O)CS(=O)C(c1ccccc1)c1ccccc1
in ch i key: YFGHCGITMMYXAQ-UHFFFAOYSA-N
in ch i: InChI=1S/C15H15NO2S/c16-14(17)11-19(18)15(12-7-3-1-4-8-12)13-9-5-2-6-10-13/h1-10,15H,11H2,(H2,16,17)
comment: Modafinil is a eugeroic (wakefulness-promoting) drug with a multi-faceted mechanism of action. In some jurisdictions this drug is classified as a controlled substance due to its possible addiction potential. It has been termed a 'smart' drug, a group of prescription medications, purchased illegally or used off-label, with alleged cognition-enhancing properties <Reference id=31256/><Reference id=31257/>.
iupac name: 2-[di(phenyl)methylsulfinyl]acetamide
xref: CHEMBL1373
synonym: Provigil®
synonym: Alertec
synonym: Modavigil
approved: t
ligand name: modafinil
type: SyntheticOrganicLigand

UCT943
in ch i key: GGOFGCMPKAWHEZ-UHFFFAOYSA-N
in ch i: InChI=1S/C22H20F3N5O/c23-22(24,25)17-7-5-15(6-8-17)19-20(26)28-13-18(29-19)14-1-3-16(4-2-14)21(31)30-11-9-27-10-12-30/h1-8,13,27H,9-12H2,(H2,26,28)
comment: UCT943 was identified from a SAR study of the 2-aminopyridines, a class of small molecules with promising antimalarial activity <Reference id=36218/>. The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
iupac name: [4-[5-amino-6-[4-(trifluoromethyl)phenyl]pyrazin-2-yl]phenyl]-piperazin-1-ylmethanone
approved: f
ligand name: UCT943
type: SyntheticOrganicLigand

ST034307
canonical SMILES: Clc1ccc2c(c1)c(=O)cc(o2)C(Cl)(Cl)Cl
isomeric SMILES: Clc1ccc2c(c1)c(=O)cc(o2)C(Cl)(Cl)Cl
in ch i key: NTDHYMSVCBGQJF-UHFFFAOYSA-N
in ch i: InChI=1S/C10H4Cl4O2/c11-5-1-2-8-6(3-5)7(15)4-9(16-8)10(12,13)14/h1-4H
comment: ST034307 is selective small-molecule inhibitor of adenylyl cyclase 1 <Reference id=36212/>. It has shown experimental analgesic properties in vivo.
iupac name: 6-chloro-2-(trichloromethyl)chromen-4-one
approved: f
ligand name: ST034307
type: SyntheticOrganicLigand

CRX-555
in ch i key: WNFNQTGQGFHQLU-NRBIUWCVSA-N
comment: CRX-555 is a synthetic Toll-like receptor 4 (TLR4) partial agonist from the Corixa Corporation <Reference id=36198/>. It is one of a series of lipid A mimetic aminoalkyl glucosaminide phosphate compounds that were synthesised with different length secondary acyl chains. CRX-555 has 8 carbon atoms in each of its 3 secondary acyl chains. The chemical structures for aminoalkyl glucosaminide phosphate lipid A mimetics including CRX-555 were originally claimed in patent US6303347B1 (now expired) TLR4 as potential adjuvants and immunoeffectors <Reference id=36200/>. A later patent (WO2008128997A1 <Reference id=36199/>) claims these compounds for prophylactic and therapeutic applications in autoimmune diseases. The partial agonist effect of CRX-555 was demonstrated in HeLa cells transfected with TLR4/MD-2/CD14 and an IL-8 luciferase promoter construct. While CRX-527 gave a maximum stimulation of almost 60-fold (at 10μg/ml), the maximum stimulation by CRX-555 at this concentration was only ~25-fold <Reference id=36198/>.
iupac name: (2S)-3-[(2R,3R,4R,5S,6R)-6-(hydroxymethyl)-3-[[(3R)-3-octanoyloxytetradecanoyl]amino]-4-[(3R)-3-octanoyloxytetradecanoyl]oxy-5-phosphonooxyoxan-2-yl]oxy-2-[[(3R)-3-octanoyloxytetradecanoyl]amino]propanoic acid
synonym: N-[(3R)-3-(Octanoyloxy)myristoyl]-O-[2-[[(3R)-3-(octanoyloxy)myristoyl]amino]-3-O-[(3R)-3-(octanoyloxy)myristoyl]-4-O-phosphono-2-deoxy-beta-D-glucopyranosyl]-L-serine
synonym: CRX555
approved: f
ligand name: CRX-555
type: SyntheticOrganicLigand

PN10
in ch i key: ZQSZVECJMJELSV-UHFFFAOYSA-N
in ch i: InChI=1S/C31H27ClN6O2/c1-20-10-11-21(16-22(20)12-13-24-19-33-28-9-5-14-35-38(24)28)6-2-3-15-37-30(39)27(36-31(37)40)17-23-18-34-29-25(23)7-4-8-26(29)32/h4-5,7-11,14,16,18-19,27,34H,2-3,6,15,17H2,1H3,(H,36,40)
comment: PN10 is a <Ligand id=5890/>/necrostatin hybrid molecule that inhibits RIPK1-driven necroptosis <Reference id=36186/>. The compound retains most of ponatinib's in vivo activity, but with improved selectivity conferred by the necrostatin component.
iupac name: 5-[(7-chloro-1H-indol-3-yl)methyl]-3-[4-[3-(2-imidazo[1,2-b]pyridazin-3-ylethynyl)-4-methylphenyl]butyl]imidazolidine-2,4-dione
approved: f
ligand name: PN10
type: SyntheticOrganicLigand

noradrenaline
canonical SMILES: NCC(c1ccc(c(c1)O)O)O
isomeric SMILES: NCC(c1ccc(c(c1)O)O)O
in ch i key: SFLSHLFXELFNJZ-UHFFFAOYSA-N
in ch i: InChI=1S/C8H11NO3/c9-4-8(12)5-1-2-6(10)7(11)3-5/h1-3,8,10-12H,4,9H2
comment: A racemic mixture of (+)-noradrenaline and (-)-noradrenaline. The structure show here does not specify stereochemistry and represents the mixture.
iupac name: 4-(2-amino-1-hydroxyethyl)benzene-1,2-diol
xref: CHEMBL432
synonym: norepinephrine
synonym: Norepirenamine
synonym: Adrenor
synonym: Arterenol
synonym: Levarterenol
synonym: Norartrinal
synonym: Levophed
approved: f
ligand name: noradrenaline
type: MetaboliteLigand

GSK-7975A
in ch i key: CPYTVBALBFSXSH-UHFFFAOYSA-N
in ch i: InChI=1S/C18H12F5N3O2/c19-13-2-1-3-14(20)16(13)17(28)24-15-6-7-26(25-15)9-10-4-5-11(27)8-12(10)18(21,22)23/h1-8,27H,9H2,(H,24,25,28)
comment: GSK-7975A was designed as a calcium-release activated calcium (CRAC) channel inhibitor <Reference id=36177/>. The structure is claimed as Example 36 in Glaxo patent US20120053150A1 <Reference id=36176/>. GSK-7975A inhibits (blocks) the Orai1 component of the CRAC channel complex <Reference id=36173/>.
iupac name: 2,6-difluoro-N-[1-[[4-hydroxy-2-(trifluoromethyl)phenyl]methyl]pyrazol-3-yl]benzamide
synonym: GSK7975A
synonym: example 36 [US20120053150A1]
approved: f
ligand name: GSK-7975A
type: SyntheticOrganicLigand

CM4620
in ch i key: QQMKTHUGOQDEIL-UHFFFAOYSA-N
comment: CM4620 is an investigational Orai1 inhibitor <Reference id=36172/>. It is likely to be compound I as claimed in Calcimedica's patent WO2016138472A1 <Reference id=36172/>.
iupac name: N-[5-(6-chloro-2,2-difluoro-1,3-benzodioxol-5-yl)pyrazin-2-yl]-2-fluoro-6-methylbenzamide
synonym: CM 4620
synonym: CM-4620
synonym: compound I [WO2016138472A1]
approved: f
ligand name: CM4620
type: SyntheticOrganicLigand

pyronaridine
in ch i key: DJUFPMUQJKWIJB-UHFFFAOYSA-N
in ch i: InChI=1S/C29H32ClN5O2/c1-37-26-9-8-24-28(33-26)27(23-7-6-21(30)16-25(23)32-24)31-22-14-19(17-34-10-2-3-11-34)29(36)20(15-22)18-35-12-4-5-13-35/h6-9,14-16,36H,2-5,10-13,17-18H2,1H3,(H,31,32)
comment: Pyronaridine is a benzonaphthyridine derivative with potent antimalarial activity. The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
iupac name: 4-[(7-chloro-2-methoxybenzo[b][1,5]naphthyridin-10-yl)amino]-2,6-bis(pyrrolidin-1-ylmethyl)phenol
xref: CHEMBL35228
synonym: Malaridine®
synonym: 7351
approved: f
ligand name: pyronaridine
type: SyntheticOrganicLigand

AN13762
in ch i key: VNWPYEKDGLKRAV-UHFFFAOYSA-N
in ch i: InChI=1S/C17H18BN3O5/c1-10-13(4-3-11-7-25-18(24)15(10)11)26-14-6-19-12(5-20-14)16(22)21-8-17(2,23)9-21/h3-6,23-24H,7-9H2,1-2H3
comment: AN13762 is a preclinical antimalarial candidate optimized from the benzoxaboroles, a novel class of boron-containing compound <Reference id=36162/>. The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
iupac name: 1-{5-[(1-hydroxy-7-methyl-1,3-dihydro-2,1-benzoxaborol-6-yl)oxy]pyrazine-2-carbonyl}-3-methylazetidin-3-ol
xref: CHEMBL4072916
synonym: AN762
approved: f
ligand name: AN13762
type: SyntheticOrganicLigand

Compound 9 [doi:10.26434/chemrxiv.7072592.v1]
canonical SMILES: C=CC(=O)NCCOc1ccc(cc1)c1[nH]c2c(C#N)cnn2c(=O)c1C(C)C
isomeric SMILES: C=CC(=O)NCCOc1ccc(cc1)c1[nH]c2c(C#N)cnn2c(=O)c1C(C)C
in ch i key: GAWCCMHWAMQURK-UHFFFAOYSA-N
in ch i: InChI=1S/C21H21N5O3/c1-4-17(27)23-9-10-29-16-7-5-14(6-8-16)19-18(13(2)3)21(28)26-20(25-19)15(11-22)12-24-26/h4-8,12-13,25H,1,9-10H2,2-3H3,(H,23,27)
comment: The compound (from a pre-print) is selective KDM5 covalent inhibitor designed to target cysteine residues only present in the KDM5 sub-family <Reference id=36158/>. Target engagement and ChIP-seq analysis showed that compound 7 inhibited KDM5B in cells and induced a global increase of the H3K4me3 mark at transcriptional start sites. KDM5B is thus involved in the epigenetic regulatory pathway of immune response and potential targets for antipathogen and anticancer immunotherapy.
approved: f
ligand name: Compound 9 [doi:10.26434/chemrxiv.7072592.v1]
type: SyntheticOrganicLigand

DS-8500a
in ch i key: LRXRIKVDAVVQCP-SPLOXXLWSA-N
in ch i: InChI=1S/C25H26FN3O5/c1-3-21(33-18-9-6-16(7-10-18)22(31)15-4-5-15)25-28-23(29-34-25)17-8-11-19(20(26)12-17)24(32)27-14(2)13-30/h6-12,14-15,21,30H,3-5,13H2,1-2H3,(H,27,32)/t14-,21-/m1/s1
comment: Orally available, selective GPR119 agonist, upregulates glucagon-like peptide-1 and enhances glucose-dependent insulin secretion and improves glucose homeostasis in type 2 diabetic rats.
iupac name: 4-[5-[(1R)-1-[4-(cyclopropanecarbonyl)phenoxy]propyl]-1,2,4-oxadiazol-3-yl]-2-fluoro-N-[(2R)-1-hydroxypropan-2-yl]benzamide
approved: f
ligand name: DS-8500a
type: SyntheticOrganicLigand

kinase inhibitor 2 [PMID: 30199702]
in ch i key: PRJNNPMIUGYOST-MEMLXQNLSA-N
in ch i: InChI=1S/C26H32N8/c1-17(2)22-16-30-34-24(22)32-25(31-21-12-10-20(27)11-13-21)33-26(34)29-15-18-6-8-19(9-7-18)23-5-3-4-14-28-23/h3-9,14,16-17,20-21H,10-13,15,27H2,1-2H3,(H2,29,31,32,33)/t20-,21-
comment: This compound is reported by Compain et al. (2018) as the protein kinase inhibitor component of a β-glucuronidase-responsive albumin-binding prodrug that was designed as a novel cancer therapeutic <Reference id=36133/>. The biological activity of inhibitor 2 is blocked when it is incoprorated in the enzyme-responsive prodrug. The active inhibitor is released only in the presence of β-glucuronidase (e.g. as exists in the tumour microenvironment), so should faciliate selective delivery of the drug to the tumour whilst minimising systemic off-target and adverse effects. Compound 2 is a multi-kinase inhibitor with a similar selectivity profile as <Ligand id=6035/>, but with additional potent inhibitory activity at DYRK3 and GSK3.
iupac name: 8-(propan-2-yl)-N4-{[4-(pyridin-2-yl)phenyl]methyl}-N2-[(1r,4r)-4-aminocyclohexyl]pyrazolo[1,5-a][1,3,5]triazine-2,4-diamine
approved: f
ligand name: kinase inhibitor 2 [PMID: 30199702]
type: SyntheticOrganicLigand

diflapolin
in ch i key: FGXLEECGXSDIMM-UHFFFAOYSA-N
comment: Diflapolin is reported as the first dual inhibitor of <Ligand id=5183/> and soluble epoxide hydrolase <Reference id=36132/>. Whilst 5-LOX activating protein facilitates 5-LOX-mediated conversion of arachidonic acid to pro-inflammatory leukotrienes, soluble epoxide hydrolase (sEH) degrades anti-inflammatory epoxyeicosatrienoic acids (EETs). Dual inhibition might therefore offer increased efficacy as an anti-inflammatory intervention compared to single target agents.
iupac name: 1-[4-(1,3-benzothiazol-2-ylmethoxy)-2-methylphenyl]-3-(3,4-dichlorophenyl)urea
approved: f
ligand name: diflapolin
type: SyntheticOrganicLigand

5-LOX inhibitor 2m [PMID: 30199704]
in ch i key: GCBYJNQEZBSRJO-UHFFFAOYSA-N
in ch i: InChI=1S/C29H22N2O2S/c1-33-25-19-17-21(18-20-25)26-28(27(32)22-11-5-2-6-12-22)34-29(30-26)31(23-13-7-3-8-14-23)24-15-9-4-10-16-24/h2-20H,1H3
comment: Compound 2m is reported as a competitive inhibitor of the 5-lipoxygenase (5-LOX) enzyme. It was developed for anti-inflammatory potential <Reference id=36119/>. 2m was the most active inhibtor identified from the thiazole series in this pharmacophore modeling study. The thiazole series of compounds was designed with the aim of reducing the hepatotoxicity that is associated with N-hydroxyurea class 5-LOX inhibitors <Reference id=36124/> such as <Ligand id=5297/>, atreleuton (ABT-761; PubChem CID 3086671) <Reference id=36123/> and MLN-977 (PubChem CID 9905233) <Reference id=36122/>. 2m is devoid of radical scavenging activity.
iupac name: (2-(diphenylamino)-4-(4-methoxyphenyl)thiazol-5-yl)(phenyl)methanone
approved: f
ligand name: 5-LOX inhibitor 2m [PMID: 30199704]
type: SyntheticOrganicLigand

CRAC channel inhibitor 1 [PMID: 26256403]
canonical SMILES: CCC(c1ccc(cc1)C)NC(=O)Nc1ccc(cc1)Cl
isomeric SMILES: CCC(c1ccc(cc1)C)NC(=O)Nc1ccc(cc1)Cl
in ch i key: FKBYZUDELOWDJW-UHFFFAOYSA-N
in ch i: InChI=1S/C17H19ClN2O/c1-3-16(13-6-4-12(2)5-7-13)20-17(21)19-15-10-8-14(18)9-11-15/h4-11,16H,3H2,1-2H3,(H2,19,20,21)
comment: Inhibitor 1 inhibits the ORAI1 protein component of the CRAC channel <Reference id=35944/>. The chemical structure represents a novel ORAI1-specific chemotype that is suitable for the development of more refined CRAC channel inhibitors.
iupac name: 3-(4-chlorophenyl)-1-[1-(4-methylphenyl)propyl]urea
xref: CHEMBL3923438
approved: f
ligand name: CRAC channel inhibitor 1 [PMID: 26256403]
type: SyntheticOrganicLigand

RORC2 inverse agonist 66 [PMID: 30130103]
in ch i key: BIHPJIJLDNUDGH-UHFFFAOYSA-N
in ch i: InChI=1S/C26H26F3N5O2/c1-15(2)25(36)34-9-7-17(8-10-34)19-14-33(3)23-21(19)22(26(27,28)29)20(13-31-23)32-24(35)18-6-4-5-16(11-18)12-30/h4-6,11,13-15,17H,7-10H2,1-3H3,(H,32,35)
comment: This compound is reported as an orally active, inverse agonist of the nuclear hormone receptor RORγt (RORC2) <Reference id=36117/>. RORγt is a drug target that is being expoited for the treatment of autoimmune conditions, as its inhibition reduces production of pro-inflammatory IL-17. The chemical structure is claimed as Example 5 in Pfizer's patent WO2016046755A1 <Reference id=36118/>.
iupac name: 3-cyano-N-[1-methyl-3-[1-(2-methylpropanoyl)piperidin-4-yl]-4-(trifluoromethyl)pyrrolo[2,3-b]pyridin-5-yl]benzamide
synonym: example 5 [WO2016046755A1]
approved: f
ligand name: RORC2 inverse agonist 66 [PMID: 30130103]
type: SyntheticOrganicLigand

BTK inhibitor 16 [PMID: 30122225]
in ch i key: FVEYIFISRORTDD-ROUUACIJSA-N
in ch i: InChI=1S/C26H24N4O4/c1-2-24(31)30-16-17-14-18(30)15-29(17)23-13-12-22(25(27)32)26(28-23)34-21-10-8-20(9-11-21)33-19-6-4-3-5-7-19/h2-13,17-18H,1,14-16H2,(H2,27,32)/t17-,18-/m0/s1
comment: This compound is reported as an irreversible, covalent inhibitor of Bruton's tyrosine kinase (BTK) <Reference id=36100/>. It is compound 23 (example 90) as claimed in Merck's patent US20160264548A1 <Reference id=36101/>. Because of its expression pattern on B cells, macrophages, neutrophils, and monocytes (NOT T cells) and its essential role in B lymphocyte development and function, BTK continues to be investigated as a valid therapeutic target for the treatment of diseases that involve B-cell and/or macrophage activation (e.g. B-cell malignancies, asthma and rheumatoid arthritis). <Ligand id=6912/> was the first-in-class small molecule BTK inhibitor to reach the clinic. Unfortunately, ibrutinib causes severe adverse effects that are in the main, attributed to its off-target profile. As a result, second-generation BTK inhibitors with optimised structures and improved selectivity are being developed. Inhibitor 16 described here, exhibits comparable cellular potency to ibrutinib but has a higher kinome selectivity against undesirable off-targets.
iupac name: 2-(4-phenoxyphenoxy)-6-[(1S,4S)-2-prop-2-enoyl-2,5-diazabicyclo[2.2.1]heptan-5-yl]pyridine-3-carboxamide
synonym: example 90 [US20160264548]
approved: f
ligand name: BTK inhibitor 16 [PMID: 30122225]
type: SyntheticOrganicLigand

LIT-927
in ch i key: BYYRNPIGDRRGLJ-UHFFFAOYSA-N
in ch i: InChI=1S/C17H13ClN2O3/c1-23-16-8-11(4-7-15(16)21)14-9-13(19-17(22)20-14)10-2-5-12(18)6-3-10/h2-9,21H,1H3,(H,19,20,22)
comment: LIT-927 is a small molecule that binds to and neutralises the chemokine CXCL12 <Reference id=36091/>. It has been termed a 'neutraligand'. LIT-927 was developed as an alternative strategy to inhibitors for CXCL12's cognate receptors CXCR4 or CXCR7, as a potential anti-inflammatory agent.
iupac name: 4-(4-Chlorophenyl)-6-(4-hydroxy-3-methoxyphenyl)pyrimidin-2(1H)-one
synonym: compound 57 [PMID: 30106292]
approved: f
ligand name: LIT-927
type: SyntheticOrganicLigand

AChE reactivator 2
in ch i key: AEGVBHAVNJPGMI-WGARJPEWSA-O
in ch i: InChI=1S/C23H25ClN4O2/c24-15-8-10-20-18(13-15)23(17-6-1-2-7-19(17)28-20)25-12-4-3-5-16-9-11-22(29)21(27-16)14-26-30/h8-11,13-14,29-30H,1-7,12H2,(H,25,28)/p+1/b26-14-
comment: This compound was developed using structure-based optimization, as an antidote for acetylcholinesterase (AChE) inhibition by organophosphorus nerve agents <Reference id=36090/>. The mechanism of enzyme reactivation depends on antidote-induced displacement of the phosphyl group from AChE's active-site serine. The main goal of the optimization campaign was to design an AChE reactivator with improved efficacy and brain penetrance compared to existing antidotes. In in vitro AChE reactivation assays, reactivator 2 outperformed the reference reactivators 2-PAM, HI-6, and obidoxime for AChE inhibited by various organophosphate nerve agents (VX, a sarin surrogate, tabun and ethyl papaoxon). Kinetic measurements and structural studies have confirmed the potential efficacy of reactivator 2 but it has not yet been evaluated in vivo.
approved: f
ligand name: AChE reactivator 2
type: SyntheticOrganicLigand

compound 6 [PMID: 30125504]
in ch i key: ZUJOXCIHOKDDRE-UHFFFAOYSA-N
in ch i: InChI=1S/C29H41N7O3/c1-5-8-23-28(38)35(3)24-18-30-29(33-26(24)36(23)21-9-6-7-10-21)32-22-12-11-19(17-25(22)39-4)27(37)31-20-13-15-34(2)16-14-20/h11-12,17-18,20-21,23H,5-10,13-16H2,1-4H3,(H,31,37)(H,30,32,33)
comment: Compound 6 was discovered as part of the same structure-guided design campaign as <Ligand id=10072/>, but in contrast is selective for polo like kinase 1 (PLK1) over BRD4-BD1 <Reference id=36089/>. Dual BRD4/PLK1 inhibitor 23 and compound 6 will allow dissection of the contributions made by inhibition of each target to the desired anti-cancer potential of this polypharmacology approach.
iupac name: (R)-4-((8-Cyclopentyl-5-methyl-6-oxo-7-propyl-5,6,7,8-tetrahydropteridin-2-yl)amino)-3-methoxy-N-(1-methylpiperidin-4-yl)benzamide
approved: f
ligand name: compound 6 [PMID: 30125504]
type: SyntheticOrganicLigand

compound 17l [PMID: 26288691]
isomeric SMILES: COc1ccc(cc1OC)/C=C/c1ccccc1N1C(=O)c2c(C1=O)cccc2
in ch i key: MKFOSSOUEAENMG-ACCUITESSA-N
in ch i: InChI=1S/C24H19NO4/c1-28-21-14-12-16(15-22(21)29-2)11-13-17-7-3-6-10-20(17)25-23(26)18-8-4-5-9-19(18)24(25)27/h3-15H,1-2H3/b13-11+
comment: Compound 17l is a liver X receptor antagonist <Reference id=35890/>.
xref: CHEMBL3623107
approved: f
ligand name: compound 17l [PMID: 26288691]
type: SyntheticOrganicLigand

dual BRD4/PLK1 inhibitor 23
in ch i key: HTPNGOWITIWAHM-UHFFFAOYSA-N
in ch i: InChI=1S/C31H43N7O3/c1-20-30(40)37(3)26-19-32-31(35-28(26)38(20)23-8-4-5-9-23)34-25-13-12-21(18-27(25)41-24-10-6-7-11-24)29(39)33-22-14-16-36(2)17-15-22/h12-13,18-20,22-24H,4-11,14-17H2,1-3H3,(H,33,39)(H,32,34,35)
comment: This compound was designed as a dual inhibitor of the BET family protein BRD4 and polo like kinase 1 (PLK1) to investigate the potential of synergistic inhibition of these two proteins as an anti-cancer therapy <Reference id=36089/>. Compound 23 is an equipotent inhibitor of BRD4-BD1 and PLK1 that will facilitate exploration of this polypharmacological approach as a cancer treatment.
iupac name: (R)-4-((8-Cyclopentyl-5,7-dimethyl-6-oxo-5,6,7,8-tetrahydropteridin-2-yl)amino)-3-(cyclopentyloxy)-N-(1-methylpiperidin-4-yl)benzamide
synonym: compound 23 [PMID: 30125504]
approved: f
ligand name: dual BRD4/PLK1 inhibitor 23
type: SyntheticOrganicLigand

isoquinoline 17 [PMID: 30122040]
in ch i key: SDNGUWKKARNBMG-UHFFFAOYSA-N
comment: Isoquinoline 17 binds to KEAP1 and acts as a functional Nrf2 activator <Reference id=36085/>. By inhibiting the KEAP1-Nrf2 protein-protein interaction it increases the quantity of Nrf2 protein that is available to transclocate to the nucleus and transactivate transcription of Nrf2-responsive genes in vitro. Nrf2 activators that exploit this mechanism are considered to be promising leads for the development of a novel class of antioxidant, antiinflammatory, and anticancer agents <Reference id=36086/>.
iupac name: 2-(N-{4-[N-(carboxymethyl)4-methoxybenzenesulfonamido]isoquinolin-1-yl}4-methoxybenzenesulfonamido)acetic acid
approved: f
ligand name: isoquinoline 17 [PMID: 30122040]
type: SyntheticOrganicLigand

aprocitentan
in ch i key: DKULOVKANLVDEA-UHFFFAOYSA-N
comment: Endothelin receptor antagonist and a pharmacologically active metabolite of macitentan.
iupac name: 5-(4-bromophenyl)-4-[2-(5-bromopyrimidin-2-yl)oxyethoxy]-6-(sulfamoylamino)pyrimidine
synonym: ACT-132577
approved: f
ligand name: aprocitentan
type: SyntheticOrganicLigand

A-769662
in ch i key: CTESJDQKVOEUOY-UHFFFAOYSA-N
in ch i: InChI=1S/C20H12N2O3S/c21-9-14-18(24)17-15(10-26-20(17)22-19(14)25)12-7-5-11(6-8-12)13-3-1-2-4-16(13)23/h1-8,10,23H,(H2,22,24,25)
comment: A-769662 is a small molecule activator of AMP-activated protein kinase (AMPK). Its chemical structure was originally disclosed by Cool et al. (2006) <Reference id=36074/>, in which it was used to demonstrate that AMPK activation is a feasible approach for the treatment of the metabolic syndrome and type 2 diabetes. A-769662 activates AMPK both allosterically (as evidenced by its ability to activate a mutant AMPK γ subunit that is resistant to endogenous AMP-induced activation) and by inhibiting dephosphorylation of AMPK on Thr172 <Reference id=23012/>. A-769662 is suitable as as experimental tool to understand the physiological roles of AMPK in vitro and in vivo. Use of A-769662 has also confirmed AMPK's role as an autophagy target, whose activation is able to ameliorate neurodegeneration in animal models <Reference id=36075/>. AMPK activation induces autophagy in an mTOR-independent manner, so limits the risk of the potentially detrimental effects that mTOR inhibition may have on important cellular pathways in addition to autophagy.
iupac name: 4-hydroxy-3-[4-(2-hydroxyphenyl)phenyl]-6-oxo-7H-thieno[2,3-b]pyridine-5-carbonitrile
xref: CHEMBL512504
synonym: A769662
synonym: A 769662
approved: f
ligand name: A-769662
type: SyntheticOrganicLigand

RasGRP activator 1
isomeric SMILES: CCCC(C(=O)OCC1(CO)OC(=O)/C(=C/c2cn(c3c2cccc3)C)/C1)CCC
in ch i key: SIWILCBNYOGJQH-LDADJPATSA-N
in ch i: InChI=1S/C24H31NO5/c1-4-8-17(9-5-2)22(27)29-16-24(15-26)13-18(23(28)30-24)12-19-14-25(3)21-11-7-6-10-20(19)21/h6-7,10-12,14,17,26H,4-5,8-9,13,15-16H2,1-3H3/b18-12+
comment: This is a DAG-indololactone class compound that was developed as an activator of RAS guanyl releasing proteins (RasGRP) that can discriminate between RasGRPs and protein kinase C (PKC) isoforms <Reference id=36062/>.
iupac name: [(4E)-2-(hydroxymethyl)-4-[(1-methylindol-3-yl)methylidene]-5-oxooxolan-2-yl]methyl 2-propylpentanoate
xref: CHEMBL519741
synonym: compound 1 [PMID: 24794745]
approved: f
ligand name: RasGRP activator 1
type: SyntheticOrganicLigand

GlyT1 inhibitor 51b
in ch i key: GOGNWHCPOVLYOW-NOZRDPDXSA-N
in ch i: InChI=1S/C26H33N3O3S/c30-33(31,18-20-7-8-20)27-21-15-29(16-21)22-9-10-26-24(14-22)23(13-19-5-2-1-3-6-19)25(17-32-26)28-11-4-12-28/h1-3,5-6,9-10,14,20-21,23,25,27H,4,7-8,11-13,15-18H2/t23-,25+/m1/s1
comment: Inhibitor 51b is a selective and competitive glycine transporter 1 (GlyT1) inhibitor that is being examined for anti-schizophrenia potential <Reference id=36044/>. The chemical structure was obtained using the SMILES string that was supplied in the original J Med Chem article by Amberg et al. (2018) <Reference id=36044/>. GlyT1 inhibition up-regulates the hypofunctional NMDA-mediated neurotransmission that underlies schizophrenic symptoms. Inhibitor 51b was a further optimisation of <Ligand id=10064/>, with an improved efflux ratio compared to 27a (i.e. it has a reduced level of interaction with the efflux transporter P-glycoprotein).
iupac name: N-[1-[(3R,4R)-3-(azetidin-1-yl)-4-benzyl-3,4-dihydro-2H-chromen-6-yl]azetidin-3-yl]-1-cyclopropylmethanesulfonamide
approved: f
ligand name: GlyT1 inhibitor 51b
type: SyntheticOrganicLigand

GlyT1 inhibitor 27a
in ch i key: BIPXSEJLJGIGOE-RPBOFIJWSA-N
in ch i: InChI=1S/C26H32N4O3S/c1-29-18-26(27-19-29)34(31,32)28-12-15-33-22-10-8-21-9-11-25(30-13-5-14-30)24(23(21)17-22)16-20-6-3-2-4-7-20/h2-4,6-8,10,17-19,24-25,28H,5,9,11-16H2,1H3/t24-,25+/m1/s1
comment: Inhibitor 27a is a selective and competitive glycine transporter 1 (GlyT1) inhibitor that is being examined for anti-schizophrenia potential <Reference id=36044/>. The chemical structure was obtained using the SMILES string that was supplied in the original J Med Chem article by Amberg et al. (2018) <Reference id=36044/>, and it is one of the examples claimed in patent WO2010092180 <Reference id=36047/>. GlyT1 inhibition up-regulates the hypofunctional NMDA-mediated neurotransmission that underlies schizophrenic symptoms.
iupac name: N-[2-[[(7S,8R)-7-(azetidin-1-yl)-8-benzyl-5,6,7,8-tetrahydronaphthalen-2-yl]oxy]ethyl]-1-methylimidazole-4-sulfonamide
synonym: compound (7S,8R)-27a
approved: f
ligand name: GlyT1 inhibitor 27a
type: SyntheticOrganicLigand

CDK12 inhibitor 2
in ch i key: HDJBGURZVALLMD-KWQFAZJVSA-N
in ch i: InChI=1S/C32H32N6O2/c1-37-22-26(10-18-31(37)39)25-8-13-28(14-9-25)38(32(40)35-20-23-5-3-2-4-6-23)29-15-11-27(12-16-29)36-30-17-7-24(19-33)21-34-30/h2-10,13-14,17-18,21-22,27,29H,11-12,15-16,20H2,1H3,(H,34,36)(H,35,40)/t27-,29-
comment: This compound is a novel and selective cyclin-dependent kinase 12 (CDK12) and CDK13 inhibitor <Reference id=36035/>. It is a chemical probe that is suitable for functional studies of CDK12, and a scaffold for further drug discovery efforts. CDK12 is an oncology drug target as its inhibition sensitises cancer cells to DNA-damaging reagents and DNA-repair inhibitors. The chemical structure was generated from the SMILES string supplied with the original J Med Chem article by Ito et al. (2018) <Reference id=36035/>.
iupac name: 3-Benzyl-1-(trans-4-((5-cyanopyridin-2-yl)amino)cyclohexyl)-1-(4-(1-methyl-6-oxo-1,6-dihydropyridin-3-yl)phenyl)urea
approved: f
ligand name: CDK12 inhibitor 2
type: SyntheticOrganicLigand

exo-THPO
canonical SMILES: NC1CCCc2c1c(O)no2
isomeric SMILES: NC1CCCc2c1c(O)no2
in ch i key: OAJLTKZYCPGQMS-UHFFFAOYSA-N
in ch i: InChI=1S/C7H10N2O2/c8-4-2-1-3-5-6(4)7(10)9-11-5/h4H,1-3,8H2,(H,9,10)
iupac name: 4-amino-4,5,6,7-tetrahydro-1,2-benzoxazol-3-ol
xref: CHEMBL150865
approved: f
ligand name: exo-THPO
type: SyntheticOrganicLigand

ABX-1431
in ch i key: SQZJGTOZFRNWCX-UHFFFAOYSA-N
in ch i: InChI=1S/C20H22F9N3O2/c21-18(22,23)14-4-3-13(15(11-14)31-5-1-2-6-31)12-30-7-9-32(10-8-30)17(33)34-16(19(24,25)26)20(27,28)29/h3-4,11,16H,1-2,5-10,12H2
comment: ABX-1431 is a potent, orally available, and selective covalent (irreversible) inhibitor of monoacylglycerol lipase (MGLL) <Reference id=36033/>. It is one of the chemical structures that are claimed in patent WO2013103973A1 <Reference id=36034/>. MGLL inhibition increases the level of the endogenous cannabinoid receptor agonist 2-arachidonoylglycerol (2-AG) and CB1 receptor signalling in the central nervous system, and reduces arachidonic acid and eicosanoid levels to better regulate neurotransmission. Modulation of these neurotransmitter molecules induces antinociceptive, anxiolytic, and antineuroinflammatory effects, but is devoid of the psychoactive effects that would be produced by direct cannabinoid receptor activation. Target engagement by ABX-1431 in the brain has been confirmed in a PET occupancy study <Reference id=36034/>.
iupac name: 1,1,1,3,3,3-hexafluoropropan-2-yl 4-[[2-pyrrolidin-1-yl-4-(trifluoromethyl)phenyl]methyl]piperazine-1-carboxylate
xref: CHEMBL3945728
synonym: ABX1431
synonym: ABX 1431
synonym: compound 28 [PMID: 30067909]
synonym: example 82 [WO2013103973A1]
synonym: compound 9aq [WO2013103973A1]
approved: f
ligand name: ABX-1431
type: SyntheticOrganicLigand

azelaprag
in ch i key: DOMQFIFVDIAOOT-ROUUACIJSA-N
in ch i: InChI=1S/C25H29N7O4S/c1-15-10-19(14-26-11-15)24-29-30-25(32(24)22-20(35-5)8-7-9-21(22)36-6)31-37(33,34)18(4)17(3)23-27-12-16(2)13-28-23/h7-14,17-18H,1-6H3,(H,30,31)/t17-,18-/m0/s1
comment: Azelaprag (AMG 986) is an apelin receptor agonist that is claimed in Amgen's patent WO2016187308A1 (as example 263) <Reference id=36026/>. The chemical structure is identical to that submitted to the WHO for the INN azelaprag. Apelin receptor agonists are being pursued for their clinical inotropic potential in the treatment of heart failure.
iupac name: (2S,3R)-N-[4-(2,6-dimethoxyphenyl)-5-(5-methylpyridin-3-yl)-1,2,4-triazol-3-yl]-3-(5-methylpyrimidin-2-yl)butane-2-sulfonamide
synonym: example 263 [WO2016187308A1]
synonym: AMG986
synonym: AMG-986
synonym: AMG 986
approved: f
ligand name: azelaprag
type: SyntheticOrganicLigand

Ac-SDKP
in ch i key: HJDRXEQUFWLOGJ-AJNGGQMLSA-N
in ch i: InChI=1S/C20H33N5O9/c1-11(27)22-14(10-26)18(31)24-13(9-16(28)29)17(30)23-12(5-2-3-7-21)19(32)25-8-4-6-15(25)20(33)34/h12-15,26H,2-10,21H2,1H3,(H,22,27)(H,23,30)(H,24,31)(H,28,29)(H,33,34)/t12-,13-,14-,15-/m0/s1
comment: Ac-SDKP is a synthetic tetrapeptide and a substrate for ACE, and a negative regulator of haematopoietic stem cell differentiation and is a potent antifibrotic agent. It is involved in angiogenesis and regulation of the immune response by blocking the proliferation of lymphocytes.
iupac name: (2S)-1-[(2S)-2-[[(2S)-2-[[(2S)-2-acetamido-3-hydroxypropanoyl]amino]-4-hydroxy-4-oxobutanoyl]amino]-6-aminohexanoyl]pyrrolidine-2-carboxylic acid
synonym: seraspenide
synonym: goralatide
approved: f
ligand name: Ac-SDKP
type: PeptideLigand

miricorilant
in ch i key: GVVUZBSCYAVFTI-IYARVYRRSA-N
in ch i: InChI=1S/C24H23F3N2O2/c25-24(26,27)19-8-4-5-15(13-19)14-20-21(28-23(31)29-22(20)30)18-11-9-17(10-12-18)16-6-2-1-3-7-16/h1-8,13,17-18H,9-12,14H2,(H2,28,29,30,31)/t17-,18-
comment: Miricorilant (CORT118335) is a potent, orally active non-steroidal glucocorticoid receptor (GR) antagonist that is being developed by Corcept Therapeutics <Reference id=36024/>. Selective GR antagonists are being investigated for their potential to mitigate antipsychotic-induced weight gain, a beneficial activity that was first identified using the dual GR/progesterone receptor antagonist <Ligand id=2805/> <Reference id=36025/>. Hunt et al. (2010) specify CORT118335 with the InChIKey GVVUZBSCYAVFTI-IYARVYRRSA-N and as the trans isomer (or the (1r,4r) isomer) <Reference id=36024/>, which corresponds to the chemical structure submitted to the WHO for the INN miricorilant. Note that PubChem lists this compound in the form without any specified stereochemistry, with PubChem CID 66550324, and that ChEMBL record the cis (or (1s,4s)) isomer as CHEMBL2204043 (InChIKey GVVUZBSCYAVFTI-HDICACEKNA-N).
synonym: CORT 118335
synonym: C-118335
synonym: compound 7 [PMID: 23131342]
synonym: C118335
synonym: CORT118335
approved: f
ligand name: miricorilant
type: SyntheticOrganicLigand

olorinab
in ch i key: ACSQLTBPYZSGBA-GMXVVIOVSA-N
in ch i: InChI=1S/C18H23N5O3/c1-18(2,3)13(9-24)20-17(25)15-12-7-10-6-11(10)16(12)23(21-15)14-8-22(26)5-4-19-14/h4-5,8,10-11,13,24H,6-7,9H2,1-3H3,(H,20,25)/t10-,11-,13+/m0/s1
comment: Olorinab (APD371) is a cannabinoid CB2 receptor agonist that was developed by Arena Pharmaceuticals as a potential treatment for chronic pain <Reference id=36023/>. In vitro, APD371 is as efficacious as the CB2 receptor full agonist <Ligand id=730/> (as determined by measuring and comparing Emax values), and has limited tachyphylaxis liability (i.e. it does cause agonist-induced desensitization by disrupting recycling of internalized agonist-activated receptors back to the plasma membrane) .
synonym: APD-371
synonym: APD 371
synonym: compound 6 [PMID: 29259753]
synonym: APD371
approved: f
ligand name: olorinab
type: SyntheticOrganicLigand

CY-09
isomeric SMILES: S=C1S/C(=C/c2ccc(cc2)C(=O)O)/C(=O)N1Cc1cccc(c1)C(F)(F)F
in ch i key: DJTINRHPPGAPLD-DHDCSXOGSA-N
comment: CY-09 is a direct inhibitor of NLRP3 <Reference id=36022/>. The compound binds to the ATP-binding motif of NLRP3 and blocks its ATPase activity. As a result NLRP3 inflammasome assembly is suppressed resulting in an anti-inflammatory effect.
iupac name: 4-[(Z)-[4-oxo-2-sulfanylidene-3-[[3-(trifluoromethyl)phenyl]methyl]-1,3-thiazolidin-5-ylidene]methyl]benzoic acid
xref: CHEMBL488823
approved: f
ligand name: CY-09
type: SyntheticOrganicLigand

CG200745
in ch i key: AUGCSOFQTDKPSO-RGVLZGJSSA-N
in ch i: InChI=1S/C24H33N3O4/c1-27(2)17-9-16-25-24(29)20(11-4-3-5-15-23(28)26-30)18-31-22-14-8-12-19-10-6-7-13-21(19)22/h6-8,10-14,30H,3-5,9,15-18H2,1-2H3,(H,25,29)(H,26,28)/b20-11+
comment: CG200745 is a pan-histone deacetylase inhibitor that is being developed by Crystal Genomics <Reference id=36013/><Reference id=36011/>. It is being explored for anti-tumourigenic <Reference id=36016/><Reference id=36012/><Reference id=36011/><Reference id=36013/> and anti-fibrotic potential <Reference id=36015/><Reference id=36017/>.
iupac name: (E)-N-(3-dimethylaminopropyl)-N'-hydroxy-2-(naphthalen-1-yloxymethyl)oct-2-enediamide
synonym: CG-200745
synonym: CG-2
synonym: HDCG-0745
approved: f
ligand name: CG200745
type: SyntheticOrganicLigand

sphingomyelin synthase 2 inhibitor 15w
in ch i key: VZWFUUUUCXTDJT-UHFFFAOYSA-N
comment: Compound 15w is a selective, orally active inhibitor of human sphingomyelin synthase 2 (SMS2) <Reference id=36010/>.
iupac name: 4-[(2-chloro-5-fluorophenyl)methoxy]-N-(pyridin-3-yl)-1,2-benzoxazol-3-amine
synonym: compound 15w [PMID: 30074791]
approved: f
ligand name: sphingomyelin synthase 2 inhibitor 15w
type: SyntheticOrganicLigand

PF-06282999
in ch i key: ICYNYWFGIDGBRD-UHFFFAOYSA-N
comment: PF-06282999 is a thiouracil-based, irreversible mechanism-based, investigational myeloperoxidase (MPO) inhibitor <Reference id=36003/> that was advanced as a clinical candidate, primarily as a novel treatment for cardiovascular diseases <Reference id=36004/>.
iupac name: 2-[6-(5-chloro-2-methoxyphenyl)-4-oxo-2-sulfanylidenepyrimidin-1-yl]acetamide
xref: CHEMBL3633460
synonym: PF06282999
synonym: PF 06282999
synonym: compound 8 [PMID: 26509551]
approved: f
ligand name: PF-06282999
type: SyntheticOrganicLigand

verdiperstat
canonical SMILES: CC(OCCn1c(=S)[nH]c(=O)c2c1cc[nH]2)C
isomeric SMILES: CC(OCCn1c(=S)[nH]c(=O)c2c1cc[nH]2)C
in ch i key: FVJCUZCRPIMVLB-UHFFFAOYSA-N
in ch i: InChI=1S/C11H15N3O2S/c1-7(2)16-6-5-14-8-3-4-12-9(8)10(15)13-11(14)17/h3-4,7,12H,5-6H2,1-2H3,(H,13,15,17)
comment: Verdiperstat is a thiouracil-based, irreversible mechanism-based, investigational myeloperoxidase (MPO) inhibitor <Reference id=36000/>. It was designed to delay progression in patients with neurodegenerative brain disorders.
iupac name: 1-(2-propan-2-yloxyethyl)-2-sulfanylidene-5H-pyrrolo[2,3-e]pyrimidin-4-one
synonym: AZD3241
synonym: AZD-3241
approved: f
ligand name: verdiperstat
type: SyntheticOrganicLigand

aminopyridine 2
canonical SMILES: O=C(Nc1ccc(cc1)Br)NCc1ccc(nc1)N
isomeric SMILES: O=C(Nc1ccc(cc1)Br)NCc1ccc(nc1)N
in ch i key: NNDXEGUWCFIHTD-UHFFFAOYSA-N
in ch i: InChI=1S/C13H13BrN4O/c14-10-2-4-11(5-3-10)18-13(19)17-8-9-1-6-12(15)16-7-9/h1-7H,8H2,(H2,15,16)(H2,17,18,19)
comment: Aminopyridine 2 is a mechanism based myeloperoxidase (MPO) inhibitor <Reference id=35994/>. It is an irreversible inhibitor. Aminopyridine 2 is orally bioavailable and offers a pharmacological tool that is suitable for evaluating the importance of MPO in preclinical models of chronic inflammatory diseases.
iupac name: 1-((6-aminopyridin-3-yl)methyl)-3-(4-bromophenyl)urea
approved: f
ligand name: aminopyridine 2
type: SyntheticOrganicLigand

R283
canonical SMILES: O=CCCSc1n(C)cc[n+]1C
isomeric SMILES: O=CCCSc1n(C)cc[n+]1C
in ch i key: NAQRMIYTJDQSRI-UHFFFAOYSA-N
in ch i: InChI=1S/C8H13N2OS/c1-9-4-5-10(2)8(9)12-7-3-6-11/h4-6H,3,7H2,1-2H3/q+1
comment: R283 is an active site-directed inhibitor of intracellular transglutaminase activity.
iupac name: 3-(1,3-dimethylimidazol-1-ium-2-yl)sulfanylpropanal
synonym: 1,3-Dimethyl-2[(oxopropyl)thio]imidazolium
approved: f
ligand name: R283
type: SyntheticOrganicLigand

ERW1041E
in ch i key: FDWIPZHANLQVMF-RDJZCZTQSA-N
in ch i: InChI=1S/C20H21BrN4O4/c21-18-9-15(29-24-18)11-23-19(26)17-6-3-7-25(17)20(27)28-12-13-8-14-4-1-2-5-16(14)22-10-13/h1-2,4-5,8,10,15,17H,3,6-7,9,11-12H2,(H,23,26)/t15-,17-/m0/s1
comment: ERW1041E is a transglutaminase inhibitor <Reference id=35985/>. We drew the structure as depicted in Chrobok et al. (2018) <Reference id=35983/>, with the indicated stereochemistry (but note that the IUPAC they provide is for the flat structure that is represented by PubChem CID 11619556).
iupac name: quinolin-3-ylmethyl (2S)-2-[[(5S)-3-bromo-4,5-dihydro-1,2-oxazol-5-yl]methylcarbamoyl]pyrrolidine-1-carboxylate
xref: CHEMBL219514
approved: f
ligand name: ERW1041E
type: SyntheticOrganicLigand

indole-3-carbinol
canonical SMILES: OCc1c[nH]c2c1cccc2
isomeric SMILES: OCc1c[nH]c2c1cccc2
in ch i key: IVYPNXXAYMYVSP-UHFFFAOYSA-N
in ch i: InChI=1S/C9H9NO/c11-6-7-5-10-9-4-2-1-3-8(7)9/h1-5,10-11H,6H2
comment: Indole-3-carbinol (I3C) is a secondary plant metabolite produced in Brassica family vegetables. It has been reported as an aryl hydrocarbon receptor agonist, although its affinity is very low and it therefore may not be a significant agonist of the AhR in vivo <Reference id=35967/>. Anticarcinogenic and antitumourigenic properties of I3C have been reported in various types of cancer cells <Reference id=35968/><Reference id=35969/><Reference id=35970/>.
iupac name: 1H-indol-3-ylmethanol
xref: CHEMBL155625
synonym: I3C
synonym: 3-hydroxymethylindole
synonym: 3-indolemethanol
synonym: 3-indolylcarbinol
approved: f
ligand name: indole-3-carbinol
type: SyntheticOrganicLigand

indolo[3,2-b]carbazole
canonical SMILES: c1ccc2c(c1)c1cc3=Nc4c(c3cc1=N2)cccc4
isomeric SMILES: c1ccc2c(c1)c1cc3=Nc4c(c3cc1=N2)cccc4
in ch i key: HLVSZSQYBQCBQG-UHFFFAOYSA-N
in ch i: InChI=1S/C18H10N2/c1-3-7-15-11(5-1)13-9-18-14(10-17(13)19-15)12-6-2-4-8-16(12)20-18/h1-10H
comment: Indolo(3,2-b)carbazole is a potent agonist of the aryl hydrocarbon receptor (AhR) <Reference id=35967/>. It is a metabolite of indole-3-carbinol (I3C) whihc is found in Brassica family vegetables, and which is formed in the acid pH of the stomach.
iupac name: indolo[3,2-b]carbazole
synonym: ICZ-carbazole
synonym: ICZ
approved: f
ligand name: indolo[3,2-b]carbazole
type: SyntheticOrganicLigand

cintirorgon
in ch i key: GULSIMHVQYBADX-FQEVSTJZSA-N
in ch i: InChI=1S/C27H23F6NO6S/c1-26(2,24(35)36)13-20-14-34(41(37,38)21-5-3-4-17(11-21)27(31,32)33)22-10-15(6-7-23(22)39-20)16-8-18(28)12-19(9-16)40-25(29)30/h3-12,20,25H,13-14H2,1-2H3,(H,35,36)/t20-/m0/s1
comment: Cintirorgon (LYC-55716) is a first-in-class, oral, selective RORγ agonist that is being developed by Lycera as a novel immuno-oncology agent. It is one of the chemical structures claimed in Lycera's patent WO2016201225A1 <Reference id=35963/>.
iupac name: 3-[(2S)-6-[3-(difluoromethoxy)-5-fluorophenyl]-4-[3-(trifluoromethyl)phenyl]sulfonyl-2,3-dihydro-1,4-benzoxazin-2-yl]-2,2-dimethylpropanoic acid
synonym: LYC55716
synonym: LYC 55716
synonym: compound 32J [WO2016201225A1]
synonym: LYC-55716
approved: f
ligand name: cintirorgon
type: SyntheticOrganicLigand

abivertinib
in ch i key: UOFYSRZSLXWIQB-UHFFFAOYSA-N
in ch i: InChI=1S/C26H26FN7O2/c1-3-23(35)29-17-5-4-6-19(15-17)36-25-20-9-10-28-24(20)31-26(32-25)30-18-7-8-22(21(27)16-18)34-13-11-33(2)12-14-34/h3-10,15-16H,1,11-14H2,2H3,(H,29,35)(H2,28,30,31,32)
comment: Abivertinib (AC0010) is an orally active, irreversible EGFR inhibitor (third generation) that selectively targets mutated EGFRs, and which was designed to overcome T790M-induced resistance in tumours <Reference id=35960/><Reference id=43598/>. It also inhibits BTK, thus offering extended clinical utility <Reference id=35961/>. We show the structure for the free base form of the compound. The maleate salt formulation is known as STI-5656.
iupac name: N-[3-[[2-[3-fluoro-4-(4-methylpiperazin-1-yl)anilino]-7H-pyrrolo[2,3-d]pyrimidin-4-yl]oxy]phenyl]prop-2-enamide
synonym: AC0010MA
synonym: avitinib (superceded INN)
synonym: AC0010
synonym: FUJOVEE®
approved: f
ligand name: abivertinib
type: SyntheticOrganicLigand

carfentanil
in ch i key: YDSDEBIZUNNPOB-UHFFFAOYSA-N
in ch i: InChI=1S/C24H30N2O3/c1-3-22(27)26(21-12-8-5-9-13-21)24(23(28)29-2)15-18-25(19-16-24)17-14-20-10-6-4-7-11-20/h4-13H,3,14-19H2,1-2H3
comment: Carfentanil is an analogue of the synthetic opioid analgesic <Ligand id=1626/>, but it is ~100 times more potent.
iupac name: methyl 1-(2-phenylethyl)-4-(phenyl-propanoylamino)piperidine-4-carboxylate
xref: CHEMBL290429
synonym: carfentanyl
synonym: Wildnil®
synonym: R-31833
synonym: R31833
synonym: (4-methoxycarbonyl)fentanyl
synonym: R 33,799
approved: f
ligand name: carfentanil
type: SyntheticOrganicLigand

compound 6 [PMID: 29579323]
in ch i key: OKFVCWAYHJMQFA-UHFFFAOYSA-N
in ch i: InChI=1S/C19H14ClNO4/c20-13-8-9-15(19(23)24)16(10-13)21-18(22)11-25-17-7-3-5-12-4-1-2-6-14(12)17/h1-10H,11H2,(H,21,22)(H,23,24)
comment: Compound 6 is reported as a selective inhibitor of the calcium-activated non-selective cation channel TRPM4 <Reference id=35926/>. To date (August 2018) this is the first report of a selective sub‐micromolar TRPM4 inhibitor. It will facilitate experiments to better understand the role of TRPM4 function in human diseases, and help provide clues for clinical lead development.
iupac name: 4-chloro-2-[(2-naphthalen-1-yloxyacetyl)amino]benzoic acid
xref: CHEMBL1408302
synonym: NBA
approved: f
ligand name: compound 6 [PMID: 29579323]
type: SyntheticOrganicLigand

compound 5 [PMID: 29579323]
canonical SMILES: O=C(Nc1cc(Cl)ccc1C(=O)O)COc1ccccc1Cl
isomeric SMILES: O=C(Nc1cc(Cl)ccc1C(=O)O)COc1ccccc1Cl
in ch i key: CVQCJPCMPGKEDH-UHFFFAOYSA-N
in ch i: InChI=1S/C15H11Cl2NO4/c16-9-5-6-10(15(20)21)12(7-9)18-14(19)8-22-13-4-2-1-3-11(13)17/h1-7H,8H2,(H,18,19)(H,20,21)
comment: Compound 5 is reported as a selective inhibitor of the calcium-activated non-selective cation channel TRPM4 <Reference id=35926/>. It will facilitate experiments to better understand the role of TRPM4 function in human diseases, and help provide clues for clinical lead development.
iupac name: 4-chloro-2-[[2-(2-chlorophenoxy)acetyl]amino]benzoic acid
synonym: CBA
approved: f
ligand name: compound 5 [PMID: 29579323]
type: SyntheticOrganicLigand

eltanexor
isomeric SMILES: NC(=O)/C(=C/n1cnc(n1)c1cc(cc(c1)C(F)(F)F)C(F)(F)F)/c1cncnc1
in ch i key: JFBAVWVBLRIWHM-AWNIVKPZSA-N
in ch i: InChI=1S/C17H10F6N6O/c18-16(19,20)11-1-9(2-12(3-11)17(21,22)23)15-27-8-29(28-15)6-13(14(24)30)10-4-25-7-26-5-10/h1-8H,(H2,24,30)/b13-6+
comment: Eltanexor (KPT-8602) is a second-generation, orally bioavailable, selective inhibitor of the nuclear export protein XPO1, that works in the same way as its first-in-class relation <Ligand id=10036/>. In comparison to selinexor, eltanexor exhibits much lower brain penetration, and this appears to reduce the central nervous system-mediated side effects of anorexia and weight loss detected with selinexor therapy <Reference id=35920/>. Eltanexor is being investigated for therapeutic antineoplastic potential <Reference id=35920/><Reference id=35921/><Reference id=35922/>.
iupac name: (E)-3-[3-[3,5-bis(trifluoromethyl)phenyl]-1,2,4-triazol-1-yl]-2-pyrimidin-5-ylprop-2-enamide
synonym: KPT-8602
synonym: KPT8602
synonym: KPT 8602
approved: f
ligand name: eltanexor
type: SyntheticOrganicLigand

selinexor
in ch i key: DEVSOMFAQLZNKR-RJRFIUFISA-N
in ch i: InChI=1S/C17H11F6N7O/c18-16(19,20)11-5-10(6-12(7-11)17(21,22)23)15-26-9-30(29-15)4-1-14(31)28-27-13-8-24-2-3-25-13/h1-9H,(H,25,27)(H,28,31)/b4-1-
comment: Selinexor (KPT-330) is an inhibitor of the nuclear export protein XPO1 (a.k.a. exportin 1) that is being developed as an anti-neoplastic agent by Karyopharm Therapeutics. It is a first-in-class inhibitor that exploits a novel mechanism of action compared to existing chemotherapeutics <Reference id=35908/><Reference id=35909/><Reference id=37933/>. The chemical structure is claimed in patent WO2013019561A1 (as compound 70) <Reference id=35911/>.
iupac name: (Z)-3-[3-[3,5-bis(trifluoromethyl)phenyl]-1,2,4-triazol-1-yl]-N'-pyrazin-2-ylprop-2-enehydrazide
xref: CHEMBL3545185
synonym: KPT-330
synonym: KPT330
synonym: compound 70 [WO2013019561A1]
synonym: Xpovio®
synonym: Nexpovio®
approved: t
ligand name: selinexor
type: SyntheticOrganicLigand

IMB-808
in ch i key: XITZPIXICJOKTF-UHFFFAOYSA-N
in ch i: InChI=1S/C18H15F3N2O4/c1-23(9-15(24)22-12-4-3-11(19)16(20)17(12)21)18(25)10-2-5-13-14(8-10)27-7-6-26-13/h2-5,8H,6-7,9H2,1H3,(H,22,24)
comment: IMB-808 is a liver X receptor partial agonist that shows anti-atherosclerotic potential <Reference id=35888/><Reference id=35889/>. It exhibits dual LXRα/β agonism but is devoid of the common lipogenic side effects of LXR full agonists <Reference id=35889/>.
iupac name: N-methyl-N-[2-oxo-2-[(2,3,4-trifluorophenyl)amino]ethyl]-2,3-dihydro-1,4-benzodioxine-7-carboxamide
xref: CHEMBL1316881
approved: f
ligand name: IMB-808
type: SyntheticOrganicLigand

pralsetinib
in ch i key: GBLBJPZSROAGMF-RWYJCYHVSA-N
in ch i: InChI=1S/C27H32FN9O2/c1-16-11-22(33-23-12-17(2)35-36-23)34-25(31-16)19-7-9-27(39-4,10-8-19)26(38)32-18(3)20-5-6-24(29-13-20)37-15-21(28)14-30-37/h5-6,11-15,18-19H,7-10H2,1-4H3,(H,32,38)(H2,31,33,34,35,36)/t18-,19-,27+/m0/s1
comment: Pralsetinib (BLU-667) is a second-generation selective RET kinase inhibitor that is being developed by Blueprint Medicines <Reference id=35886/>. It is Compound 130 in patent US20170121312A1 and our structure was drawn from the image therein <Reference id=35887/>. Selective RET inhibitors have oncology potential for the treatment of solid tumours with oncogenic RET alterations (e.g. constitutively activating RET point mutations and RET gene rearrangements). They are expected to offer more effective anti-tumour efficacy in RET-driven tumours than the currently available multi-kinase inhibitors (such as <Ligand id=5887/> and <Ligand id=5717/>) that have limited anti-RET activity, and which have exhibited poor therapeutic responses in this defined patient group.
iupac name: N-[(1S)-1-[6-(4-fluoropyrazol-1-yl)pyridin-3-yl]ethyl]-1-methoxy-4-[4-methyl-6-[(5-methyl-1H-pyrazol-3-yl)amino]pyrimidin-2-yl]cyclohexane-1-carboxamide
synonym: BLU-667
synonym: BLU667
synonym: Gavreto®
approved: t
ligand name: pralsetinib
type: SyntheticOrganicLigand

lusutrombopag
in ch i key: NOZIJMHMKORZBA-KJCUYJGMSA-N
comment: Lusutrombopag is an orally bioavailable, nonpeptidyl, small molecule thrombopoietin (TPO) receptor agonist <Reference id=35883/> that was developed by Shionogi in Japan. It was the second TPO receptor agonist to receive FDA approval in 2018 (<Ligand id=9953/> was the first).
iupac name: (E)-3-[2,6-dichloro-4-[[4-[3-[(1S)-1-hexoxyethyl]-2-methoxyphenyl]-1,3-thiazol-2-yl]carbamoyl]phenyl]-2-methylprop-2-enoic acid
xref: CHEMBL2107831
synonym: Mulpleta®
synonym: S-888711
synonym: S888711
synonym: S 888711
approved: t
ligand name: lusutrombopag
type: SyntheticOrganicLigand

RTI-13951-33
in ch i key: XCHHIKJEGXHKLQ-UJTWYAIMSA-N
in ch i: InChI=1S/C28H33N3O3/c1-19(34-3)26(29)17-31(28(32)25-16-24(25)27-6-4-5-15-30-27)23-13-11-22(12-14-23)21-9-7-20(8-10-21)18-33-2/h4-15,19,24-26H,16-18,29H2,1-3H3/t19-,24-,25-,26-/m1/s1
comment: RTI-13951-33 is a potent and selective GPR88 agonist that is suitable for in vivo investigations <Reference id=35880/>. It is a derivative of <Ligand id=7798/>. No significant off-target activity of RTI-13951-33 across a range of 38 GPCRs, ion channels, and neurotransmitter transporters has been detected <Reference id=35880/>.
approved: f
ligand name: RTI-13951-33
type: SyntheticOrganicLigand

VCE-004.3
in ch i key: CIEWIZBPWBLHSB-PZJWPPBQSA-N
in ch i: InChI=1S/C26H39NO3/c1-6-8-10-12-20-23(27-15-11-9-7-2)25(29)22(26(30)24(20)28)21-16-18(5)13-14-19(21)17(3)4/h16,19,21,27,29H,3,6-15H2,1-2,4-5H3/t19-,21+/m0/s1
comment: VCE-004.3 is a semi-synthetic cannabidiol quinone derivative <Reference id=35875/>. It acts as a dual PPARγ/CB2 receptor agonist and CB1 receptor modulator. The structure is claimed in patent WO2015158381 <Reference id=35876/>. VCE-004.3 is functional (promotes transactivation) on PPARγ via a binding site that is distinct from the canonical <Ligand id=1056/> binding site on this nuclear receptor.
iupac name: 4-hydroxy-3-[(1R,6R)-3-methyl-6-prop-1-en-2-ylcyclohex-2-en-1-yl]-6-pentyl-5-(pentylamino)cyclohexa-3,5-diene-1,2-dione
approved: f
ligand name: VCE-004.3
type: SyntheticOrganicLigand

AM6545
in ch i key: XBHQLFVDGLPBCK-UHFFFAOYSA-N
comment: High affinity and selective CB1 antagonist
iupac name: 5-[4-(4-cyanobut-1-ynyl)phenyl]-1-(2,4-dichlorophenyl)-N-(1,1-dioxo-1,4-thiazinan-4-yl)-4-methylpyrazole-3-carboxamide
synonym: AM-6545
synonym: AM 6545
approved: f
ligand name: AM6545
type: SyntheticOrganicLigand

MJN110
in ch i key: BEADRWVIFHOSGN-UHFFFAOYSA-N
comment: MJN110 is a potent selective inhibitor of MAGL, the enzyme predominantly responsible for the degradation of the endocannabinoid 2-arachidonoylglycerol (2-AG).
iupac name: (2,5-dioxopyrrolidin-1-yl) 4-[bis(4-chlorophenyl)methyl]piperazine-1-carboxylate
synonym: MJN-110
synonym: MJN 110
approved: f
ligand name: MJN110
type: SyntheticOrganicLigand

cycloguanil
canonical SMILES: Clc1ccc(cc1)N1C(=NC(=NC1(C)C)N)N
isomeric SMILES: Clc1ccc(cc1)N1C(=NC(=NC1(C)C)N)N
in ch i key: QMNFFXRFOJIOKZ-UHFFFAOYSA-N
in ch i: InChI=1S/C11H14ClN5/c1-11(2)16-9(13)15-10(14)17(11)8-5-3-7(12)4-6-8/h3-6H,1-2H3,(H4,13,14,15,16)
comment: Cycloguanil is an antifolate compound and a metabolite of the antimalarial drug <Ligand id=9676/>. The INN-assigned compound is formulated with <Ligand id=2920/>.
iupac name: 1-(4-chlorophenyl)-6,6-dimethyl-1,3,5-triazine-2,4-diamine
xref: CHEMBL747
approved: f
ligand name: cycloguanil
type: SyntheticOrganicLigand

piperaquine
in ch i key: UCRHFBCYFMIWHC-UHFFFAOYSA-N
in ch i: InChI=1S/C29H32Cl2N6/c30-22-2-4-24-26(20-22)32-8-6-28(24)36-16-12-34(13-17-36)10-1-11-35-14-18-37(19-15-35)29-7-9-33-27-21-23(31)3-5-25(27)29/h2-9,20-21H,1,10-19H2
comment: Piperaquine is a 4-aminoquinoline antimalarial compound. The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
iupac name: 7-chloro-4-[4-[3-[4-(7-chloroquinolin-4-yl)piperazin-1-yl]propyl]piperazin-1-yl]quinoline
xref: CHEMBL303933
approved: t
ligand name: piperaquine
type: SyntheticOrganicLigand

MMV253
in ch i key: HKPQFVAUXAZCDY-OAHLLOKOSA-N
in ch i: InChI=1S/C24H32FN9/c1-14-10-21(31-33(14)5)28-23-19(34-9-8-32(4)15(2)13-34)12-26-24(30-23)29-20-11-18(17-6-7-17)22(25)16(3)27-20/h10-12,15,17H,6-9,13H2,1-5H3,(H2,26,27,28,29,30,31)/t15-/m1/s1
comment: MMV253 is the clinical lead for the triaminopyrimidines (TAPs), a novel class of antimalarial compounds identified from a phenotypic screen <Reference id=35860/>. The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
iupac name: 2-N-(4-cyclopropyl-5-fluoro-6-methylpyridin-2-yl)-5-[(3R)-3,4-dimethylpiperazin-1-yl]-4-N-(1,5-dimethylpyrazol-3-yl)pyrimidine-2,4-diamine
xref: CHEMBL4284447
synonym: AZ13721412
synonym: MMV674253
synonym: ZY19489
synonym: ZY-19489
approved: f
ligand name: MMV253
type: SyntheticOrganicLigand

LRE1
canonical SMILES: Clc1cc(nc(n1)N)N(C1CC1)Cc1cccs1
isomeric SMILES: Clc1cc(nc(n1)N)N(C1CC1)Cc1cccs1
in ch i key: PDWZXKSZLRVSEH-UHFFFAOYSA-N
in ch i: InChI=1S/C12H13ClN4S/c13-10-6-11(16-12(14)15-10)17(8-3-4-8)7-9-2-1-5-18-9/h1-2,5-6,8H,3-4,7H2,(H2,14,15,16)
comment: LRE1 is a selective allosteric inhibitor of soluble adenylyl cyclase (sAC) <Reference id=36859/>.
iupac name: 6-chloro-N4-cyclopropyl-N4-(2-thienylmethyl)-2,4-pyrimidinediamine
synonym: RU-0204277
approved: f
ligand name: LRE1
type: SyntheticOrganicLigand

ACT-451840
in ch i key: BQZUYCCCNXOADJ-TVNMEPFQSA-N
in ch i: InChI=1S/C47H54N6O3/c1-36(54)50-28-30-51(31-29-50)43-21-16-41(17-22-43)35-53(45(55)23-18-37-14-19-42(20-15-37)47(2,3)4)44(32-38-8-6-5-7-9-38)46(56)52-26-24-49(25-27-52)34-40-12-10-39(33-48)11-13-40/h5-23,44H,24-32,34-35H2,1-4H3/b23-18+/t44-/m0/s1
comment: ACT-451840 is an investigational antimalarial drug, selected from a new class of compounds identified from a phenotypic screen <Reference id=35363/><Reference id=35360/>. Chemically it is a piperazine-containing compound. The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
iupac name: (E)-N-[[4-(4-acetylpiperazin-1-yl)phenyl]methyl]-3-(4-tert-butylphenyl)-N-[(2S)-1-[4-[(4-cyanophenyl)methyl]piperazin-1-yl]-1-oxo-3-phenylpropan-2-yl]prop-2-enamide
synonym: ACT451840
synonym: Actelion-451840
approved: f
ligand name: ACT-451840
type: SyntheticOrganicLigand

ELQ-300
in ch i key: WZDNKHCQIZRDKW-UHFFFAOYSA-N
comment: ELQ-300 is a late lead candidate from a novel class of 4(1H)-quinolone-based compounds with potent antimalarial activity <Reference id=35354/>. The ELQs (endochin-like quinolones) are structural derivatives of endochin (PubChem CID 100474), which has potent antiplasmodial activity, but is highly metabolically unstable in mammals <Reference id=35356/><Reference id=35355/>. The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
iupac name: 6-chloro-7-methoxy-2-methyl-3-[4-[4-(trifluoromethoxy)phenoxy]phenyl]-1H-quinolin-4-one
xref: CHEMBL2431810
synonym: ELQ300
approved: f
ligand name: ELQ-300
type: SyntheticOrganicLigand

DSM421
in ch i key: HDLFZCDEGAWEFX-UHFFFAOYSA-N
in ch i: InChI=1S/C14H11F5N6/c1-7-5-10(22-8-3-4-9(20-6-8)14(17,18)19)25-12(21-7)23-11(24-25)13(2,15)16/h3-6,22H,1-2H3
comment: DSM421 was being developed as a backup compound to <Ligand id=9644/>, the clinical lead for the triazolopyrimidine structural class of antimalarial compounds, but it has not been progressed due to unpredicted off-target toxicity <Reference id=35352/><Reference id=40315/>. The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
iupac name: 2-(1,1-difluoroethyl)-5-methyl-N-[6-(trifluoromethyl)pyridin-3-yl]-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine
approved: f
ligand name: DSM421
type: SyntheticOrganicLigand

halofantrine
in ch i key: FOHHNHSLJDZUGQ-UHFFFAOYSA-N
comment: Halofantrine is a phenanthrene containing compound and belongs to the aryl amino alcohols, a chemical class of antimalarial drugs that includes <Ligand id=2510/>, <Ligand id=4252/> and <Ligand id=9969/>. The INN record specifies that halofantrine is a racemic mixture of stereoisomers. We show the structure without specified stereochemistry to represent the mixture. The marketed formulation contains halofantrine hydrochloride (PubChem CID 37392). The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
iupac name: 3-(dibutylamino)-1-[1,3-dichloro-6-(trifluoromethyl)phenanthren-9-yl]propan-1-ol
xref: CHEMBL1107
synonym: WR-171669
synonym: Halfan®
approved: t
ligand name: halofantrine
type: SyntheticOrganicLigand

amodiaquine
canonical SMILES: CCN(Cc1cc(ccc1O)Nc1ccnc2c1ccc(c2)Cl)CC
isomeric SMILES: CCN(Cc1cc(ccc1O)Nc1ccnc2c1ccc(c2)Cl)CC
in ch i key: OVCDSSHSILBFBN-UHFFFAOYSA-N
in ch i: InChI=1S/C20H22ClN3O/c1-3-24(4-2)13-14-11-16(6-8-20(14)25)23-18-9-10-22-19-12-15(21)5-7-17(18)19/h5-12,25H,3-4,13H2,1-2H3,(H,22,23)
comment: Amodiaquine is a 4-aminoquinoline antimalarial compound related to <Ligand id=5535/>. The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
iupac name: 4-[(7-chloroquinolin-4-yl)amino]-2-(diethylaminomethyl)phenol
xref: CHEMBL682
synonym: Flavoquine®
synonym: Camoquin®
synonym: Amdaquine®
synonym: Amoquin®
synonym: Alphaquine®
approved: t
ligand name: amodiaquine
type: SyntheticOrganicLigand

MMV024101
in ch i key: GTWOKQIGBJADIZ-UHFFFAOYSA-N
in ch i: InChI=1S/C16H12N6O2S/c17-25(23,24)12-5-10(6-18-9-12)14-1-2-15-16(22-14)13(3-4-19-15)11-7-20-21-8-11/h1-9H,(H,20,21)(H2,17,23,24)
comment: MMV024101 is one of the compounds with antimalarial activity from the Medicines for Malaria Venture (MMV) Pathogen Box. The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
iupac name: 5-[8-(1H-pyrazol-4-yl)-1,5-naphthyridin-2-yl]pyridine-3-sulfonamide
xref: CHEMBL530228
synonym: compound 8 [PMID: 29889526]
approved: f
ligand name: MMV024101
type: SyntheticOrganicLigand

compound 55 [PMID: 29889526]
in ch i key: UNHBOZVTSNPRRO-UHFFFAOYSA-N
comment: Compound 55 is the drug-like lead discovered as a result of a SAR investigation and is a 2,8-Disubstituted-1,5-naphthyridine derivative of <Ligand id=10017/> <Reference id=35340/>. The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
iupac name: 3-(8-(2-(Trifluoromethyl)pyridin-4-yl)-1,5-naphthyridin-2-yl)benzenesulfonamide
approved: f
ligand name: compound 55 [PMID: 29889526]
type: SyntheticOrganicLigand

supratinib
in ch i key: QUBHCPBWMPEXQW-NPAZBBTKSA-N
comment: Supratinib is an amphiphilic molecular analogue of the MEK inhibitor <Ligand id=5665/> <Reference id=35338/>. Structurally it is selumetinib linked to a cholesterol-based tether that ficilitates its assembly into a stable supramolecular lipid bilayer nanoparticle. Supratinib was designed to form lipid nanoparticles which would deliver improved MEK-driven anti-cancer activity compared to the parent molecule. It is predicted that such a supramolecular therapeutic could be designed to include immune check point T cell activating biologics (e.g. anti-PD-1 or anti-PD-L1 monoclonal antibodies) which could ultimately be used to enhance cancer immunotherapy. This same strategy of derivatizing a kinase inhibitor with a cholesterol anchor (in this case creating an analogue of the CSF1R inhibitor <Ligand id=8250/>) and assembling it in a supramolecular structure with a macrophage-targeting anti-SIRPα mAb (which blocks the SIRPα/CD47 anti-phagocytic signal that is exploited by some cancer cells to avoid immune destruction) has been reported to enhance phagocytosis and removal of melanoma cancer cells by tumour associated macrophages in vitro and in vivo <Reference id=35339/>.
approved: f
ligand name: supratinib
type: SyntheticOrganicLigand

cannabidiol-dimethylheptyl (-)-CBD-DMH
in ch i key: MPJURNPNPDQYSY-LEWJYISDSA-N
in ch i: InChI=1S/C25H38O2/c1-7-8-9-10-13-25(5,6)19-15-22(26)24(23(27)16-19)21-14-18(4)11-12-20(21)17(2)3/h14-16,20-21,26-27H,2,7-13H2,1,3-6H3/t20-,21+/m0/s1
comment: Cannabidiol-dimethylheptyl (-)-CBD-DMH ((-)-5'-CBD-DMH) is a synthetic homologue of <Ligand id=4150/>. Structurally the pentyl chain of cannabidiol has been replaced by a dimethylheptyl chain, and it retains the same stereochemistry as natural cannabidiol. Like cannabidiol (-)-5'-DMH-CBD is not psychotropic, has anticonvulsant activity, and is not a CB1 receptor agonist <Reference id=35323/>.
iupac name: 5-(2-methyloctan-2-yl)-2-[(1R,6R)-3-methyl-6-prop-1-en-2-ylcyclohex-2-en-1-yl]benzene-1,3-diol
synonym: (-)-5'-DMH-CBD
synonym: 1%22',1'%22-Dimethylheptylcannabidiol
synonym: 5-(1,1-Dimethylheptyl)cannabidiol
synonym: DMH-CBD
synonym: (-)-5'-CBD-DMH
approved: f
ligand name: cannabidiol-dimethylheptyl (-)-CBD-DMH
type: SyntheticOrganicLigand

dolcanatide
in ch i key: NSPHQWLKCGGCQR-HLHYUOOASA-N
comment: Guanylyl cyclase C (GC-C) agonist.
iupac name: (2R)-2-[[(1R,4S,7S,10S,13S,16R,21R,27S,34R,37S,40S)-10-(2-amino-2-oxoethyl)-34-[[(2S)-4-carboxy-2-[[(2S)-3-carboxy-2-[[(2R)-2,4-diamino-4-oxobutanoyl]amino]propanoyl]amino]butanoyl]amino]-37-(2-carboxyethyl)-27-[(1R)-1-hydroxyethyl]-4-methyl-40-(2-methylpropyl)-3,6,9,12,15,23,26,29,35,38,41-undecaoxo-7,13-di(propan-2-yl)-18,19,31,32-tetrathia-2,5,8,11,14,22,25,28,36,39,42-undecazabicyclo[14.13.13]dotetracontane-21-carbonyl]amino]-4-methylpentanoic acid
approved: f
ligand name: dolcanatide
type: PeptideLigand

vericiguat
in ch i key: QZFHIXARHDBPBY-UHFFFAOYSA-N
in ch i: InChI=1S/C19H16F2N8O2/c1-31-19(30)25-14-15(22)26-17(27-16(14)23)13-11-6-10(20)7-24-18(11)29(28-13)8-9-4-2-3-5-12(9)21/h2-7H,8H2,1H3,(H,25,30)(H4,22,23,26,27)
comment: Vericiguat is a novel oral soluble guanylate cyclase (sGC) stimulator <Reference id=35312/>. It was initially developed for potential to reduce mortality and morbidity associated with chronic heart failure with reduced ejection fraction.
iupac name: methyl N-[4,6-diamino-2-[5-fluoro-1-[(2-fluorophenyl)methyl]pyrazolo[3,4-b]pyridin-3-yl]pyrimidin-5-yl]carbamate
synonym: MK-1242
synonym: BAY-1021189
synonym: Verquvo®
approved: t
ligand name: vericiguat
type: SyntheticOrganicLigand

VU0483605
in ch i key: HJQXPBKPTGWZCF-UHFFFAOYSA-N
comment: Positive allosteric modulator at mGlu1.
iupac name: 3-Chloro-N-[3-chloro-4-(4-chloro-1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)phenyl]-2-pyridinecarboxamide
synonym: VU-0483605
synonym: VU 0483605
approved: f
ligand name: VU0483605
type: SyntheticOrganicLigand

Fumitremorgin C
in ch i key: DBEYVIGIPJSTOR-FHWLQOOXSA-N
in ch i: InChI=1S/C22H25N3O3/c1-12(2)9-18-20-15(14-7-6-13(28-3)10-16(14)23-20)11-19-21(26)24-8-4-5-17(24)22(27)25(18)19/h6-7,9-10,17-19,23H,4-5,8,11H2,1-3H3/t17-,18-,19-/m0/s1
comment: Inhibitor of ABCG2-mediated multidrug resistance.
iupac name: (5aS,12S,14aS)-1,2,3,5a,6,11,12,14a-Octahydro-9-methoxy-12-(2-methyl-1-propen-1-yl)-5H,14H-pyrrolo[1'',2'':4',5']pyrazino[1',2':1,6]pyrido[3,4-b]indole-5,14-dione
approved: f
ligand name: Fumitremorgin C
type: SyntheticOrganicLigand

Ko 143
in ch i key: NXNRAECHCJZNRF-JBACZVJFSA-N
in ch i: InChI=1S/C26H35N3O5/c1-14(2)11-20-23-17(16-8-7-15(33-6)12-19(16)27-23)13-21-24(31)28-18(25(32)29(20)21)9-10-22(30)34-26(3,4)5/h7-8,12,14,18,20-21,27H,9-11,13H2,1-6H3,(H,28,31)/t18-,20-,21-/m0/s1
comment: Potent and selective ABCG2 inhibitor.
iupac name: (3S,6S,12aS)-1,2,3,4,6,7,12,12a-Octahydro-9-methoxy-6-(2-methylpropyl)-1,4-dioxopyrazino[1',2':1,6]pyrido[3,4-b]indole-3-propanoic acid 1,1-dimethylethyl ester
synonym: Ko143
synonym: Ko-143
approved: f
ligand name: Ko 143
type: SyntheticOrganicLigand

KS 176
in ch i key: LTWQQWSXYYXVGA-UHFFFAOYSA-N
in ch i: InChI=1S/C22H19N3O5/c26-14-13-15-5-9-17(10-6-15)23-22(28)19-3-1-2-4-20(19)24-21(27)16-7-11-18(12-8-16)25(29)30/h1-12,26H,13-14H2,(H,23,28)(H,24,27)
comment: Selective ABCG2 inhibitor.
iupac name: N-[4-(2-Hydroxyethyl)phenyl]-2-[(4-nitrobenzoyl)amino]benzamide
synonym: KS176
synonym: KS-176
approved: f
ligand name: KS 176
type: SyntheticOrganicLigand

compound 17 [PMID: 29741897]
in ch i key: AOSZTAHDEDLTLQ-AZKQZHLXSA-N
comment: Compound 17 is a novel analogue of the anti-inflammatory inhalation corticosteroid <Ligand id=7434/> <Reference id=35303/>. It was designed to have improved potency, increased lung retention, and a longer duration of action than budesonide.
approved: f
ligand name: compound 17 [PMID: 29741897]
type: SyntheticOrganicLigand

KX2-361
in ch i key: CMKKPJNMYLOUCE-UHFFFAOYSA-N
in ch i: InChI=1S/C24H24FN3O2/c25-21-3-1-2-18(14-21)16-27-24(29)15-22-7-4-20(17-26-22)19-5-8-23(9-6-19)28-10-12-30-13-11-28/h1-9,14,17H,10-13,15-16H2,(H,27,29)
comment: KX2-361 is a small molecule with a dual mode of action. It is a Src kinase inhibitor and an inhibitor of tubulin polymerization <Reference id=35304/>. It is being investigated for antiproliferative potential. It is closely related to <Ligand id=7957/>, and like KX2-391 is a peptide substrate site binder rather than a competitive ATP binding site inhibitor. KX2-361 is orally bioavailable and shows a significant level of brain tissue exposure following oral administration.
iupac name: N-[(3-fluorophenyl)methyl]-2-[5-(4-morpholin-4-ylphenyl)pyridin-2-yl]acetamide
synonym: KX2361
synonym: KX2 361
synonym: KX-02
approved: f
ligand name: KX2-361
type: SyntheticOrganicLigand

GNE-131
in ch i key: FPERPEQIXLOVIK-UHFFFAOYSA-N
in ch i: InChI=1S/C23H30N4O3S/c28-31(29,18-3-4-18)26-22-25-24-21-8-20(19(12-27(21)22)17-1-2-17)30-13-23-9-14-5-15(10-23)7-16(6-14)11-23/h8,12,14-18H,1-7,9-11,13H2,(H,25,26)
comment: GNE-131 is a potent and selective hNaV1.7 inhibitor that was designed for the treatment of pain <Reference id=35299/>. Site-directed mutagenesis experiments show that GNE-131 binds within the anion binding pocket of the channel (around reside R1608).
iupac name: N-[7-(1-adamantylmethoxy)-6-cyclopropyl-[1,2,4]triazolo[4,3-a]pyridin-3-yl]cyclopropanesulfonamide
synonym: GNE 131
synonym: GNE131
synonym: compound 13 [PMID: 29737846]
approved: f
ligand name: GNE-131
type: SyntheticOrganicLigand

triple modulator 10 [PMID: 29878767]
in ch i key: CJILPLPDEJBFHA-UHFFFAOYSA-N
in ch i: InChI=1S/C31H28N4O5S/c1-35-20-23(27-19-25(15-16-28(27)35)33-31(37)32-24-9-5-3-6-10-24)17-21-13-14-22(18-29(21)40-2)30(36)34-41(38,39)26-11-7-4-8-12-26/h3-16,18-20H,17H2,1-2H3,(H,34,36)(H2,32,33,37)
comment: Triple modulator 10 has been developed as an anti-inflammatory agent with intentionally designed-in polypharamcology <Reference id=35293/>. Structurally it is a derivative of the cysteinyl-leukotriene receptor antagonist, anti-asthma drug <Ligand id=3322/> and its exploits off-target effects of this drug. Triple modulator 10 is a cysteinyl leukotriene receptor 1 (CysLT1R) antagonist, a peroxisome proliferator-activated receptor γ (PPARγ) agonist and a soluble epoxide hydrolase (sEH) inhibitor.
iupac name: N-(benzenesulfonyl)-3-methoxy-4-({1-methyl-5-[(phenylcarbamoyl)amino]-1H-indol-3-yl}methyl)benzamide
approved: f
ligand name: triple modulator 10 [PMID: 29878767]
type: SyntheticOrganicLigand

compound 52 [PMID: 28541707]
in ch i key: ZDXIDBRGTYDHBQ-UHFFFAOYSA-N
in ch i: InChI=1S/C22H20F3N7O2/c1-12(33)31-7-6-30(20(34)21(31,2)3)16-8-13(4-5-14(16)10-26)17-9-15(22(23,24)25)18-19(27)28-11-29-32(17)18/h4-5,8-9,11H,6-7H2,1-3H3,(H2,27,28,29)
comment: Compound 52 is reported as a potent and selective PI3Kδ inhibitor <Reference id=35290/>.
approved: f
ligand name: compound 52 [PMID: 28541707]
type: SyntheticOrganicLigand

gusacitinib
in ch i key: NLFLXLJXEIUQDL-UHFFFAOYSA-N
in ch i: InChI=1S/C24H28N8O2/c25-10-5-16-6-11-32(12-7-16)24-28-20-15-26-30-23(34)21(20)22(29-24)27-17-1-3-18(4-2-17)31-13-8-19(33)9-14-31/h1-4,15-16,19,33H,5-9,11-14H2,(H,30,34)(H,27,28,29)
comment: Gusacitinib (ASN002) is an orally bioavailable dual spleen tyrosine kinase (SYK)/pan Janus kinase (JAK) inhibitor that is being developed by Asana BioSciences. It is being evaluated for clinical efficacy in inflammatory and oncology settings. Not to be confused with Ascend Biopharmaceuticals immuno-oncology lead ASN-002, which is an engineered virus that expresses IFN-γ. Gusacitinib is one of the chemical structures (example 189) claimed in Asana Biosciences' patent WO2013028818A1 <Reference id=37390/>.
synonym: ASN002
synonym: ASN-002
synonym: example 189 [WO2013028818A1]
approved: f
ligand name: gusacitinib
type: SyntheticOrganicLigand

MRS4478
in ch i key: ODSCFSVBFVSJFO-UHFFFAOYSA-N
in ch i: InChI=1S/C23H15F3N4O3/c24-23(25,26)18-7-5-14(6-8-18)20-12-30(29-28-20)19-10-16(9-17(11-19)22(32)33)13-1-3-15(4-2-13)21(27)31/h1-12H,(H2,27,31)(H,32,33)
comment: MRS4478 is a P2Y14 receptor antagonist <Reference id=35286/>.
iupac name: 4'-carbamoyl-5-{4-[4-(trifluoromethyl)phenyl]-1H-1,2,3-triazol-1-yl}-[1,1'-biphenyl]-3-carboxylic acid
synonym: compound 30 [Yu et al., 2018]
approved: f
ligand name: MRS4478
type: SyntheticOrganicLigand

MRS4458
in ch i key: VYXSDIPOJBFWHQ-UHFFFAOYSA-N
comment: MRS4458 is a P2Y14 receptor antagonist <Reference id=35286/>.
iupac name: 3-{5-[(3-aminopropyl)carbamoyl]thiophen-2-yl}-5-{4-[4-(trifluoromethyl)phenyl]-1H-1,2,3-triazol-1-yl}benzoic acid
synonym: compound 20 [Yu et al., 2018]
approved: f
ligand name: MRS4458
type: SyntheticOrganicLigand

AZD3458
in ch i key: PAQUFWFUOVDUIO-NSHDSACASA-N
in ch i: InChI=1S/C20H23N3O4S2/c1-10-18(28-20(21-10)22-12(3)24)14-7-15-9-23(11(2)13-5-6-13)19(25)17(15)16(8-14)29(4,26)27/h7-8,11,13H,5-6,9H2,1-4H3,(H,21,22,24)/t11-/m0/s1
comment: Compound 15 is an orally available PI3K inhibitor with selectivity for the PI3Kγ isoform <Reference id=35279/>. This is a new isoindolinone chemotype that has not previously been used for the design of PI3K inhibitors.
xref: CHEMBL4126156
synonym: compound 15 [PMID: 29852070]
synonym: AZD-3458
approved: f
ligand name: AZD3458
type: SyntheticOrganicLigand

elobixibat
in ch i key: XFLQIRAKKLNXRQ-UUWRZZSWSA-N
in ch i: InChI=1S/C36H45N3O7S2/c1-4-6-18-36(19-7-5-2)24-39(27-16-12-9-13-17-27)28-20-30(47-3)29(21-31(28)48(44,45)25-36)46-23-32(40)38-34(26-14-10-8-11-15-26)35(43)37-22-33(41)42/h8-17,20-21,34H,4-7,18-19,22-25H2,1-3H3,(H,37,43)(H,38,40)(H,41,42)/t34-/m1/s1
comment: Elobixibat is an orally available inhibitor of the ileal bile acid transporter (IBAT or ASBT), which is the protein product of the SLC10A2 gene. It is being evaluated for clinical utility in the management of chronic constipation <Reference id=35273/><Reference id=35275/><Reference id=35276/>. The chemical structure is claimed as Example 14 in Albireo Ab's patent US20130225511A1 <Reference id=35278/> (we have chosen this iteration of the patent as it has both chemical structure images and data included in online versions).
iupac name: 2-[[(2R)-2-[[2-[(3,3-dibutyl-7-methylsulfanyl-1,1-dioxo-5-phenyl-2,4-dihydrobenzo[b][1,4]thiazepin-8-yl)oxy]acetyl]amino]-2-phenylacetyl]amino]acetic acid
xref: CHEMBL3039515
synonym: AZD7806
synonym: AZD-7806
synonym: AZD 7806
synonym: A3309
synonym: AJG533
synonym: Goofice®
synonym: 2-[[(2R)-2-[[2-[(3,3-dibutyl-7-methylsulfanyl-1,1-dioxo-5-phenyl-2,4-dihydro-1λ6,5-benzothiazepin-8-yl)oxy]acetyl]amino]-2-phenylacetyl]amino]acetic acid
approved: t
ligand name: elobixibat
type: SyntheticOrganicLigand

SH045
in ch i key: VDWLBNKHHJKPOQ-LDAQOBCYSA-N
in ch i: InChI=1S/C22H37NO3/c1-8-21(5,25)13-10-16-15(2)14-17(26-19(24)23-7)18-20(3,4)11-9-12-22(16,18)6/h8,16-18,25H,1-2,9-14H2,3-7H3,(H,23,24)/t16-,17-,18-,21+,22+/m0/s1
comment: SH045 is a TRPC6 channel blocker <Reference id=35138/>. It is a synthetic congener of the diterpene natural product (+)‐larixol (PubChem CID 11335788), which is found in the resin of the European larch, Larix decidua. In vitro and ex vivo studies suggest SH045 as a lead compound with clinical potential for the reduction of lung ischemia‐reperfusion edema (LIRE).
iupac name: (1S,4S,4aR,8aS)-4-[(3S)-3-hydroxy-3-methylpent-4-en-1-yl]-4a,8,8-trimethyl-3-methylidene-decahydronaphthalen-1-yl N-methylcarbamate
synonym: compound 19 [PMID: 29522264]
approved: f
ligand name: SH045
type: SyntheticOrganicLigand

GNE-4997
in ch i key: JNRFIKALOWSUBG-CGCKEFBRSA-N
comment: GNE-4997 is a tetrahydroindazole-containing inhibitor of the Tec family tyrosine kinase, interleukin-2-inducible tyrosine kinase (ITK) <Reference id=35272/>. ITK is involved in T cell development, differentiation, and effector function, and acts downstream of the T cell receptor (TCR) to mediate phospholipase γ-1 (PLCγ1) phosphorylation and subsequent Ca2+ mobilization.
synonym: GNE4997
synonym: GNE 4997
synonym: compound 28 [PMID: 25844760]
approved: f
ligand name: GNE-4997
type: SyntheticOrganicLigand

BMS-509744
in ch i key: ZHXNIYGJAOPMSO-UHFFFAOYSA-N
in ch i: InChI=1S/C32H41N5O4S2/c1-20-16-26(41-7)25(30(40)37-14-12-36(13-15-37)22(3)38)17-27(20)42-28-19-34-31(43-28)35-29(39)24-10-8-23(9-11-24)18-33-21(2)32(4,5)6/h8-11,16-17,19,21,33H,12-15,18H2,1-7H3,(H,34,35,39)
comment: BMS-509744 is an inhibitor of the Tec family tyrosine kinase, interleukin-2-inducible T cell kinase (ITK) <Reference id=35271/>. ITK inhibitors are being investigated for potential immunosuppressive and/or anti-inflammatory activities.
iupac name: N-[5-[5-(4-acetylpiperazine-1-carbonyl)-4-methoxy-2-methylphenyl]sulfanyl-1,3-thiazol-2-yl]-4-[(3,3-dimethylbutan-2-ylamino)methyl]benzamide
xref: CHEMBL209148
synonym: compound 3 [PMID:16682193]
synonym: BMS509744
synonym: BMS 509744
approved: f
ligand name: BMS-509744
type: SyntheticOrganicLigand

rilzabrutinib
in ch i key: LCFFREMLXLZNHE-GBOLQPHISA-N
in ch i: InChI=1S/C36H40FN9O3/c1-36(2,45-15-13-43(14-16-45)26-21-48-22-26)18-24(19-38)35(47)44-12-6-7-25(20-44)46-34-31(33(39)40-23-41-34)32(42-46)29-11-10-28(17-30(29)37)49-27-8-4-3-5-9-27/h3-5,8-11,17-18,23,25-26H,6-7,12-16,20-22H2,1-2H3,(H2,39,40,41)/b24-18+/t25-/m1/s1
comment: Rilzabrutinib (PRN1008) is an oral, reversible covalent inhibitor of Bruton's tyrosine kinase (BTK) <Reference id=38200/>. The chemical structure of PRN1008 has not been formally disclosed, and there is some uncertainty of its precise stereochemistry evident in online resources. One possible structure is claimed as Example 31 in Principia Biopharma patent WO2014039899 <Reference id=35270/> and this is depicted in PubChem CID 118325989 as the R form without E/Z specification. We show the (E,R) structure here.
iupac name: (E)-2-[(3R)-3-[4-amino-3-(2-fluoro-4-phenoxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]piperidine-1-carbonyl]-4-methyl-4-[4-(oxetan-3-yl)piperazin-1-yl]pent-2-enenitrile
xref: CHEMBL3702854
synonym: Example 31 [WO2014039899]
synonym: PRN1008
synonym: PRN-1008
approved: f
ligand name: rilzabrutinib
type: SyntheticOrganicLigand

compound 29 [Moslin et al., 2017]
in ch i key: BDYFCJQKSYBTAK-UHFFFAOYSA-N
in ch i: InChI=1S/C20H24F2N6O4/c1-20(31,10-29)4-5-24-19(30)15-9-25-18-14(23-2)8-16(27-28(15)18)26-13-7-11(21)6-12(22)17(13)32-3/h6-9,23,29,31H,4-5,10H2,1-3H3,(H,24,30)(H,26,27)
comment: Compound 29 binds to the JH2 pseudokinase domain of the Janus kinase family enzyme, TYK2 <Reference id=35266/>. Various cytokines and their receptors mediate intracellular signalling through pairs of Janus kinase family enzymes. TYK2 dimerises with JAK2 to mediate IL-12 and IL-23 signalling (both are p40 subunit containing cytokines), and with JAK1 for the IFNα/β pathway. Both of these TYK2-dependent pathways are validated as druggable targets for the development of pharmaceuticals for the treatment of autoimmune diseases. Displacement of the ATP that binds to the JH2 pseudokinase domain allosterically disrupts TYK2 catalytic activity, in a mechanism that appears to stablise the kinase in an auto-inhibitory conformation. Expolting this domain is being investigated with the aim of identifying inhibitors with improved selectivity compared to traditional orthosteric JH1 domain ATP-competitive inhibitors.
iupac name: 6-[(3,5-difluoro-2-methoxyphenyl)amino]-N-(3,4-dihydroxy-3-methylbutyl)-8-(methylamino)imidazo[1,2-b]pyridazine-3-carboxamide
approved: f
ligand name: compound 29 [Moslin et al., 2017]
type: SyntheticOrganicLigand

dimethyl itaconate
canonical SMILES: COC(=O)CC(=C)C(=O)OC
isomeric SMILES: COC(=O)CC(=C)C(=O)OC
in ch i key: ZWWQRMFIZFPUAA-UHFFFAOYSA-N
in ch i: InChI=1S/C7H10O4/c1-5(7(9)11-3)4-6(8)10-2/h1,4H2,2-3H3
comment: Dimethyl itaconate is a membrane-permeable derivative of the immunoregulatory metabolite itaconate. Itaconate is one of the most highly induced metabolites produced when activated macrophages undergo metabolic remodeling. Itaconate acts as a major physiological regulator of metabolic switching and effector functions of inflammatory macrophages. Itaconate and dimethyl itaconate inhibit production of IL-6 and IL-12 (secondary transcriptional response), but not TNF (a primary transcriptional response) following Toll-like receptor stimulation <Reference id=34997/>. Itaconate has been found to promote an electrophilic stress response (i.e. a rapid adaptive defense response) <Reference id=34996/>. An electrophilic stress response involves various mechanisms, including the nuclear translocation of the redox-sensitive transcription factor Nrf2 (nuclear factor E2-related factor 2), which senses electrophilic and oxidative stresses and protects against cellular damage via Kelch-like ECH-associated protein 1 (Keap1) <Reference id=34999/><Reference id=34998/><Reference id=35000/>. Both itaconate and dimethyl itaconate induce Nrf2-dependent and -independent responses, the Nrf2-independent response being that which involves regulation of IκBζ <Reference id=34996/>.
iupac name: dimethyl 2-methylidenebutanedioate
synonym: itaconic acid dimethyl ester
synonym: dimethylitaconate
approved: f
ligand name: dimethyl itaconate
type: SyntheticOrganicLigand

abrocitinib
in ch i key: IUEWXNHSKRWHDY-PHIMTYICSA-N
in ch i: InChI=1S/C14H21N5O2S/c1-3-6-22(20,21)18-10-7-11(8-10)19(2)14-12-4-5-15-13(12)16-9-17-14/h4-5,9-11,18H,3,6-8H2,1-2H3,(H,15,16,17)/t10-,11+
comment: Abrocitinib (PF-04965842) is a JAK inhibitor <Reference id=35258/>. X-ray crystal structures of PF-04965842 bound to both JAK1 and JAK2 have been deposited with the Protein DataBank (accession IDs 6BBU and 6BBV respectively). We used the SMILES string supplied with the article in which the structure was declared <Reference id=35258/> to generate our representation of the chemical structure. The IUPAC name in abrocitinib's INN record resolves to the same StdInChIKey as our structure. PubChem CID 78323835 represents the structure without specified stereochemistry. The JAKs are immunokinases that are molecular targets of therapeutics which are used in the treatment of immune-mediated diseases.
iupac name: N-{cis-3-[Methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino]cyclobutyl}propane-1-sulfonamide
xref: CHEMBL3655081
synonym: PF04965842
synonym: compound 25 [PMID: 29298069]
synonym: PF-04965842
synonym: Cibinqo®
approved: t
ligand name: abrocitinib
type: SyntheticOrganicLigand

GNE-8505
in ch i key: IRPVABHDSJVBNZ-QWHZDKJVSA-N
in ch i: InChI=1S/C21H24F3N5O/c22-21(23,24)16-3-12(5-26-20(16)25)17-4-18(29(27-17)6-11-1-2-11)19-14-7-28(8-15(14)19)13-9-30-10-13/h3-5,11,13-15,19H,1-2,6-10H2,(H2,25,26)/t14-,15+,19+
comment: GNE-8505 is a selective inhibitor of dual leucine zipper kinase (DLK) that is being developed by Genentech (claimed in patent WO2014111496) , with similar imidazole derivatives being claimed by the University of Texas in patent WO2018044808 <Reference id=35256/>. We have drawn the structure as depicted in Siu et al. (2018) where it is identified as compound 9 <Reference id=35240/>.
iupac name: 5-[1-(cyclopropylmethyl)-5-[(1S,5R)-3-(oxetan-3-yl)-3-azabicyclo[3.1.0]hexan-6-yl]pyrazol-3-yl]-3-(trifluoromethyl)pyridin-2-amine
xref: CHEMBL3715238
synonym: example 152 [WO2014111496]
approved: f
ligand name: GNE-8505
type: SyntheticOrganicLigand

compound 11 [PMID: 26431428]
in ch i key: GMTAOJMPNXLKJI-UHFFFAOYSA-N
in ch i: InChI=1S/C22H28N6O/c23-13-16-5-8-24-21(11-16)25-22-12-20(28(26-22)18-3-1-2-4-18)17-6-9-27(10-7-17)19-14-29-15-19/h5,8,11-12,17-19H,1-4,6-7,9-10,14-15H2,(H,24,25,26)
comment: Compound 11 is a potent, selective, and brain penetrant inhibitor of dual leucine zipper kinase (DLK, MAP3K12) <Reference id=35254/>. DLK inhibitors are being investigated for neuroprotective potential.
iupac name: 2-[[1-cyclopentyl-5-[1-(oxetan-3-yl)piperidin-4-yl]pyrazol-3-yl]amino]pyridine-4-carbonitrile
xref: CHEMBL3629013
approved: f
ligand name: compound 11 [PMID: 26431428]
type: SyntheticOrganicLigand

compound 16d [Tao et al., 2009]
in ch i key: GCRBQBQLMPBGQC-UHFFFAOYSA-N
in ch i: InChI=1S/C27H24N6O2/c1-14(2)33-21-8-5-15(35-27-28-9-4-10-29-27)11-17(21)23-18-12-30-26(34)24(18)22-16(25(23)33)6-7-20-19(22)13-32(3)31-20/h4-5,8-11,13-14H,6-7,12H2,1-3H3,(H,30,34)
comment: Compound 16d is a second generation, nanomolar inhibitor of dual leucine zipper kinase (DLK) <Reference id=35252/>. It is claimed in example 19 in Cephalon's patent US8084472 <Reference id=35253/>.
iupac name: 2‐Methyl‐11‐(1‐methylethyl)‐8‐(pyrimidin‐2‐yloxy)‐2,5,6,11,12,13‐hexahydro‐4H‐indazolo[5,4‐a]pyrrolo[3,4‐c]carbazol‐4‐one
synonym: example 19 [US8084472]
approved: f
ligand name: compound 16d [Tao et al., 2009]
type: SyntheticOrganicLigand

fluorescent MIF ligand B
in ch i key: BMCSDEYJDALUKV-UHFFFAOYSA-N
in ch i: InChI=1S/C47H40FN7O8S/c48-36-23-28(10-18-40(36)58)55-26-39(53-54-55)38-17-13-31-37(52-38)6-4-7-41(31)61-21-5-8-44(59)49-19-2-1-3-20-50-46(64)51-27-9-14-33-32(22-27)45(60)63-47(33)34-15-11-29(56)24-42(34)62-43-25-30(57)12-16-35(43)47/h4,6-7,9-18,22-26,56-58H,1-3,5,8,19-21H2,(H,49,59)(H2,50,51,64)
comment: Fluorescent MIF ligand B is reported in Cisneros et al. (2016) <Reference id=35238/>. It is a <Ligand id=9981/> (MIF) inhibitor tethered to fluorescein to generate a probe suitable for fluorescence polarization assay determination of dissociation constant (Kd) of MIF inhibitors as an alternative to the Ki or IC50 values that are obtained from tautomerization assays.
iupac name: N-{5-[({3',6'-dihydroxy-3-oxo-3H-spiro[2-benzofuran-1,9'-xanthene]-5-yl}carbamothioyl)amino]pentyl}-4-({2-[1-(3-fluoro-4-hydroxyphenyl)-1H-1,2,3-triazol-4-yl]quinolin-5-yl}oxy)butanamide
approved: f
ligand name: fluorescent MIF ligand B
type: SyntheticOrganicLigand

MIF inhibitor 3bb
in ch i key: RXHQCISHMPQZDT-UHFFFAOYSA-N
in ch i: InChI=1S/C24H15FN4O4/c25-18-12-15(7-10-22(18)30)29-13-21(27-28-29)20-9-8-17-19(26-20)5-2-6-23(17)33-16-4-1-3-14(11-16)24(31)32/h1-13,30H,(H,31,32)
comment: Compound 3bb is the most potent inhibitor of <Ligand id=9981/> (MIF) tautomerase activity identified from a SAR series by Dziedzic et al. (2015) <Reference id=35237/>. It is referred to as quinoline 20 in <Reference id=35197/>.
iupac name: 3-[2-[1-(3-fluoro-4-hydroxyphenyl)triazol-4-yl]quinolin-5-yl]oxybenzoic acid
xref: CHEMBL3917143
approved: f
ligand name: MIF inhibitor 3bb
type: SyntheticOrganicLigand

Orita-13
canonical SMILES: Oc1ccc2c(c1)occ(c2=O)c1ccc(c(c1)O)O
isomeric SMILES: Oc1ccc2c(c1)occ(c2=O)c1ccc(c(c1)O)O
in ch i key: DDKGKOOLFLYZDL-UHFFFAOYSA-N
in ch i: InChI=1S/C15H10O5/c16-9-2-3-10-14(6-9)20-7-11(15(10)19)8-1-4-12(17)13(18)5-8/h1-7,16-18H
comment: Orita-13 is a prototypical inhibitor of the tautomerase activity of <Ligand id=9981/> (MIF) <Reference id=35235/>.
iupac name: 3-(3,4-dihydroxyphenyl)-7-hydroxychromen-4-one
xref: CHEMBL13486
synonym: compound 13 [PMID: 11170644]
approved: f
ligand name: Orita-13
type: SyntheticOrganicLigand

ISO-1
canonical SMILES: COC(=O)CC1ONC(=C2C=CC(=O)C=C2)C1
isomeric SMILES: COC(=O)CC1ONC(=C2C=CC(=O)C=C2)C1
in ch i key: CLVQGFPQFNASJH-UHFFFAOYSA-N
in ch i: InChI=1S/C12H13NO4/c1-16-12(15)7-10-6-11(13-17-10)8-2-4-9(14)5-3-8/h2-5,10,13H,6-7H2,1H3
comment: ISO-1 is a prototypical inhibitor of the tautomerase activity of <Ligand id=9981/> (MIF) <Reference id=35232/>.
iupac name: methyl 2-[3-(4-oxo-1-cyclohexa-2,5-dienylidene)-1,2-oxazolidin-5-yl]acetate
xref: CHEMBL210858
synonym: IN1228
approved: f
ligand name: ISO-1
type: SyntheticOrganicLigand

vanoxerine
in ch i key: NAUWTFJOPJWYOT-UHFFFAOYSA-N
in ch i: InChI=1S/C28H32F2N2O/c29-26-12-8-24(9-13-26)28(25-10-14-27(30)15-11-25)33-22-21-32-19-17-31(18-20-32)16-4-7-23-5-2-1-3-6-23/h1-3,5-6,8-15,28H,4,7,16-22H2
comment: Competitive inhibitor of dopamine uptake, binds to the target site on the dopamine transporter (DAT). Also a potent sigma receptor ligand.
iupac name: 1-[2-[bis(4-fluorophenyl)methoxy]ethyl]-4-(3-phenylpropyl)piperazine
xref: CHEMBL281594
synonym: GBR 12909
synonym: GBR12909
synonym: GBR-12909
approved: f
ligand name: vanoxerine
type: SyntheticOrganicLigand

ganaplacide
in ch i key: BUPRVECGWBHCQV-UHFFFAOYSA-N
in ch i: InChI=1S/C22H23F2N5O/c1-22(2)21-27-19(14-3-5-15(23)6-4-14)20(26-17-9-7-16(24)8-10-17)28(21)11-12-29(22)18(30)13-25/h3-10,26H,11-13,25H2,1-2H3
comment: Ganaplacide is the optimised lead for the imidazolopiperazines (IZPs), a novel class of compounds identified from a phenotypic screen as having antimalarial activity <Reference id=35021/>. The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
iupac name: 2-amino-1-[3-(4-fluoroanilino)-2-(4-fluorophenyl)-8,8-dimethyl-5,6-dihydroimidazo[1,2-a]pyrazin-7-yl]ethanone
xref: CHEMBL2058833
synonym: GNF156
synonym: KAF156
approved: f
ligand name: ganaplacide
type: SyntheticOrganicLigand

compound 15 [PMID: 25699151]
in ch i key: HGRWHBQLRXWSLV-DEOSSOPVSA-N
in ch i: InChI=1S/C24H18F2N4O3/c25-17-4-1-7-28-20(17)13-5-6-19-15(9-13)24(12-32-23(27)30-24)16-10-18(14-3-2-8-31-11-14)29-22(26)21(16)33-19/h1,3-7,9-10H,2,8,11-12H2,(H2,27,30)/t24-/m0/s1
comment: This Amgen aminooxazoline xanthene BACE1 inhibitor was selected as one of the most potent leads ever reported (up to June 2018). It has a sub-nanomolar IC50 <Reference id=35224/>.
iupac name: (4S)-3'-(3,6-dihydro-2H-pyran-5-yl)-1'-fluoro-7'-(3-fluoropyridin-2-yl)spiro[5H-1,3-oxazole-4,5'-chromeno[2,3-c]pyridine]-2-amine
xref: CHEMBL3394220
synonym: example 385 [US8883782]
approved: f
ligand name: compound 15 [PMID: 25699151]
type: SyntheticOrganicLigand

PF‐06526290
in ch i key: NZXOWNNCAZTBDJ-UHFFFAOYSA-N
in ch i: InChI=1S/C18H18N4O3S2/c1-22(13-14-5-3-2-4-6-14)27(24,25)16-9-7-15(8-10-16)20-17(23)21-18-19-11-12-26-18/h2-12H,13H2,1H3,(H2,19,20,21,23)
comment: PF‐06526290 can exhibit both enhancement and inhibition of Nav channel function.
iupac name: 1-{4-[benzyl(methyl)sulfamoyl]phenyl}-3-(1,3-thiazol-2-yl)urea
synonym: PF06526290
approved: f
ligand name: PF‐06526290
type: SyntheticOrganicLigand

PF-04634817
in ch i key: MCRWZBYTLVCCJJ-DKALBXGISA-N
in ch i: InChI=1S/C25H36F3N5O3/c1-15(2)24(6-4-16(10-24)31-19-5-7-36-13-20(19)35-3)23(34)33-12-17-8-18(33)11-32(17)22-9-21(25(26,27)28)29-14-30-22/h9,14-20,31H,4-8,10-13H2,1-3H3/t16-,17+,18+,19+,20-,24+/m1/s1
comment: PF-04634817 is an oral dual CCR2/5 antagonist that was investigated for anti-inflammatory potential. The chemical structure of PF-04634817 is claimed (as example 13) in patent US8293903B2 <Reference id=35188/>.
iupac name: [(1S,3R)-3-[[(3S,4S)-3-methoxyoxan-4-yl]amino]-1-propan-2-ylcyclopentyl]-[(1S,4S)-5-[6-(trifluoromethyl)pyrimidin-4-yl]-2,5-diazabicyclo[2.2.1]heptan-2-yl]methanone
synonym: PF04634817
synonym: PF-4634817
synonym: PF4634817
synonym: example 13 [US8293903]
approved: f
ligand name: PF-04634817
type: SyntheticOrganicLigand

TIC10
in ch i key: VLULRUCCHYVXOH-UHFFFAOYSA-N
in ch i: InChI=1S/C24H26N4O/c1-18-7-5-6-10-20(18)16-28-23(29)21-17-26(15-19-8-3-2-4-9-19)13-11-22(21)27-14-12-25-24(27)28/h2-10H,11-17H2,1H3
comment: ONC201 (also known as TIC10 <Reference id=35150/>) is an orally active, investigational dual Akt/ERK inhibitor <Reference id=35152/>, that exerts potent anti-tumour effects that are mediated via induction of the endogenous tumour suppressor (or death ligand) <Ligand id=5065/> and its receptor DR5 (death receptor 5; TNFRSF10B). Note that although <Reference id=35152/> and <Reference id=35150/> are published by the same research group, both articles show different isomers of the chemical structure. We show the structure from their 2016 paper, which introduces ONC201 as the first-in-class imipridone anti-cancer compound <Reference id=35152/>. PubChem CID 336423 represents the alternative isomer as depicted in the 2013 paper <Reference id=35150/>.
synonym: ONC-201
synonym: TIC10
synonym: TIC-10
approved: f
ligand name: TIC10
type: SyntheticOrganicLigand

tovorafenib
in ch i key: VWMJHAFYPMOMGF-ZCFIWIBFSA-N
comment: TAK-580 (MLN2480) is an investigational pan-RAF kinase inhibitor that was developed for anti-tumour potential against solid tumours, including gliomas, and common adult RAF mutant tumours (harbouring BRAF and CRAF fusions and mutations) that metastasise to the brain. It has been optimised for CNS penetration <Reference id=35148/>. The chemical structure is claimed as example 10Da in patent US20090036419A1 <Reference id=35149/>. Day One Biopharmaceuticals licensed this inhibitor from Sunesis Pharma in 2019, at which point it was re-named DAY101. The chemical structure of TAK-580 is identical to that which was submitted to the WHO for the INN tovorafenib (proposed INN list 126, Jan 2022).
iupac name: (R)-2-(1-(6-amino-5-chloropyrimidine-4-carboxamido)ethyl)-N-(5-chloro-4-(trifluoromethyl)pyridin-2-yl)thiazole-5-carboxamide
xref: CHEMBL3348923
synonym: TAK 580
synonym: TAK580
synonym: MLN 2480
synonym: MLN-2480
synonym: MLN2480
synonym: BIIB024
synonym: example 10Da [US20090036419]
synonym: TAK-580
approved: f
ligand name: tovorafenib
type: SyntheticOrganicLigand

KO-947
in ch i key: ODIUJYZERXVGEI-UHFFFAOYSA-N
in ch i: InChI=1S/C21H17N5O/c27-21-23-18-11-19-17(20(25-24-19)15-6-8-22-9-7-15)10-16(18)13-26(21)12-14-4-2-1-3-5-14/h1-11H,12-13H2,(H,23,27)(H,24,25)
comment: KO-947 is an ERK1/2 inhibitor that is in early stage clinical development as a potential treatment for advanced solid tumours with RAS/MAPK pathway mutations. (Note: ERK1= MAPK3, ERK2= MAPK1)
iupac name: 6-benzyl-3-pyridin-4-yl-2,5-dihydro-1H-pyrazolo[4,3-g]quinazolin-7-one
synonym: KO947
synonym: KO 947
approved: f
ligand name: KO-947
type: SyntheticOrganicLigand

temuterkib
in ch i key: JNPRPMBJODOFEC-UHFFFAOYSA-N
in ch i: InChI=1S/C22H27N7O2S/c1-22(2)19-15(20(30)29(22)9-8-28-10-12-31-13-11-28)14-17(32-19)16-4-6-23-21(25-16)26-18-5-7-24-27(18)3/h4-7,14H,8-13H2,1-3H3,(H,23,25,26)
comment: LY3214996 is an ERK1/2 inhibitor that is in early stage clinical development for the potential treatment of advanced non-hematological tumours, in particular for malignancies carrying activating MAPK pathway alterations, and which are refractory to RAF and MEK inhibitors. (Note: ERK1= MAPK3, ERK2= MAPK1). The chemical structure of LY3214996 matches that for the INN compound temuterkib that was surfaced in WHO Proposed list 125 in July 2021.
iupac name: 6,6-dimethyl-2-[2-[(2-methylpyrazol-3-yl)amino]pyrimidin-4-yl]-5-(2-morpholin-4-ylethyl)thieno[2,3-c]pyrrol-4-one
synonym: LY-3214996
synonym: LY3214996
approved: f
ligand name: temuterkib
type: SyntheticOrganicLigand

MK-8353
in ch i key: KPQQGHGDBBJGFA-QNGWXLTQSA-N
in ch i: InChI=1S/C37H41N9O3S/c1-24(2)49-32-12-9-28(20-38-32)34-30-19-29(10-11-31(30)41-42-34)40-36(48)37(50-4)15-18-45(22-37)21-33(47)46-16-13-26(14-17-46)25-5-7-27(8-6-25)35-39-23-44(3)43-35/h5-13,19-20,23-24H,14-18,21-22H2,1-4H3,(H,40,48)(H,41,42)/t37-/m0/s1
comment: MK-8353 (formerly know as SCH900353) is an orally bioavailable dual mechanism ERK1/2 inhibitor, i.e. it inhibits ERK1/2 catalytic activity and phosphorylation of ERK1/2 <Reference id=35142/>. It has improved pharmacokinetic properties in comparison to <Ligand id=8056/> (a preclinical ERK1/2 inhibtor tool compound) and has shown preliminary anti-tumour efficacy in patients with BRAF or RAS mutated metastatic melanoma and colorectal cancers. (Note: ERK1= MAPK3, ERK2= MAPK1).
iupac name: (3S)-3-methylsulfanyl-1-[2-[4-[4-(1-methyl-1,2,4-triazol-3-yl)phenyl]-3,6-dihydro-2H-pyridin-1-yl]-2-oxoethyl]-N-[3-(6-propan-2-yloxypyridin-3-yl)-1H-indazol-5-yl]pyrrolidine-3-carboxamide
synonym: SCH900353
synonym: MK8353
synonym: MK 8353
approved: f
ligand name: MK-8353
type: SyntheticOrganicLigand

compound 27 [PMID: 29775310]
in ch i key: XHOJEECXVUMYMF-IQGLISFBSA-N
in ch i: InChI=1S/C29H32ClN5O4/c1-17-4-3-5-19(12-17)25(16-36)33-27(37)18(2)35-15-21-7-6-20(13-23(21)28(35)38)26-24(30)14-31-29(34-26)32-22-8-10-39-11-9-22/h3-7,12-14,18,22,25,36H,8-11,15-16H2,1-2H3,(H,33,37)(H,31,32,34)/t18-,25-/m1/s1
comment: Compound 27 is a lead ERK1/2 inhibitor that was identified using biophysical fragment screening and structure-based optimization <Reference id=35141/>. It was found to be potent, selective and orally bioavailable. Compound 27 inhibits both the catalytic kinase (phosphorylating) activity of ERK1/2, and the phosphorylation of ERK1/2. It is an alternative chemotype to <Ligand id=8056/>, but it retains the dual activity profile that was originally identified in SCH772984. Compound 27 has improved in vivo exposure compared to SCH772984. (Note: ERK1= MAPK3, ERK2= MAPK1).
iupac name: (2R)-2-[5-[5-chloro-2-(oxan-4-ylamino)pyrimidin-4-yl]-3-oxo-1H-isoindol-2-yl]-N-[(1S)-2-hydroxy-1-(3-methylphenyl)ethyl]propanamide
approved: f
ligand name: compound 27 [PMID: 29775310]
type: SyntheticOrganicLigand

H4 antagonist 48
canonical SMILES: CNC1CN(C1)c1nc2ncc(cc2n2c1nnn2)Br
isomeric SMILES: CNC1CN(C1)c1nc2ncc(cc2n2c1nnn2)Br
in ch i key: ICGICUHMULRYIQ-UHFFFAOYSA-N
in ch i: InChI=1S/C11H11BrN8/c1-13-7-4-19(5-7)10-11-16-17-18-20(11)8-2-6(12)3-14-9(8)15-10/h2-3,7,13H,4-5H2,1H3
comment: Compound 48 is an orally active, selective histamine H4 receptor antagonist that was developed as a potential therapy for the pruritis and inflammation associated with atopic dermatitis <Reference id=34679/>.
approved: f
ligand name: H4 antagonist 48
type: SyntheticOrganicLigand

ferroquine
in ch i key: IRJOHJGUSPNBRI-UHFFFAOYSA-N
in ch i: InChI=1S/C18H19ClN3.C5H5.Fe/c1-22(2)12-14-5-3-4-13(14)11-21-17-8-9-20-18-10-15(19)6-7-16(17)18;1-2-4-5-3-1;/h4,6-10H,5,11-12H2,1-2H3,(H,20,21);1-3H,4H2;
comment: Ferroquine is a 4-aminoquinoline antimalarial compound with a novel ferrocenic group in its side chain. The ferrocenic group causes rendering problems, with different images of the chemical structure found across web resources. We show the structure provided by NIH US National Library of Medicine (InChIKey IRJOHJGUSPNBRI-UHFFFAOYSA-N). PubChem provide a different InChIKey DLYPREQTTOHKSM-UHFFFAOYSA-N with two structural representations PubChem CID 56841801 (link in table below) and PubChem CID 76419023. The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
synonym: SSR97193
approved: f
ligand name: ferroquine
type: SyntheticOrganicLigand

artefenomel
in ch i key: XLCNVWUKICLURR-UHFFFAOYSA-N
in ch i: InChI=1S/C28H39NO5/c1-3-26(31-14-11-29-9-12-30-13-10-29)4-2-22(1)23-5-7-27(8-6-23)32-28(34-33-27)24-16-20-15-21(18-24)19-25(28)17-20/h1-4,20-21,23-25H,5-19H2
comment: Artefenomel is a synthetic ozonide (synthetic peroxide), a class of compound that retains the endoperoxide bridge of the <Ligand id=9954/> class of antimalarials but also contains the sterically bulky amantadine ring, which increases blood plasma stability <Reference id=35292/>. The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
iupac name: 4-{2-{4-(cis-dispiro[adamantane-2,3'-[1,2,4]trioxolane- 5',1''-cyclohexane]-4''-yl)phenoxy]ethyl}morpholine
synonym: OZ439
approved: f
ligand name: artefenomel
type: SyntheticOrganicLigand

compound 11h [PMID: 29808961]
in ch i key: GTJYIEXTEWAMFX-UHFFFAOYSA-N
in ch i: InChI=1S/C28H22F2N6O2/c1-16-26(17(2)38-33-16)19-8-10-24-22(12-19)27(18-6-4-3-5-7-18)35(28(37)31-24)14-21-15-36(34-32-21)25-11-9-20(29)13-23(25)30/h3-13,15,27H,14H2,1-2H3,(H,31,37)
comment: Compound 11h is a selective BRD4 inhibitor, which has demonstrated anti-tumour potential in vitro <Reference id=35139/>. Docking studies show that compound 11h's mode of interaction is similar to that of <Ligand id=7518/>, in that both inhibitors act as acetyllysine mimics and occupy the hydrophobic acetyllysine-binding pocket in BRD4. Compound 11h exhibits modestly improved anti-proliferative activity against leukemia cells in vitro compared to <Ligand id=7511/>.
iupac name: 3-{[1-(2,4-difluorophenyl)-1H-1,2,3-triazol-4-yl]methyl}-6-(3,5-dimethyl-1,2-oxazol-4-yl)-4-phenyl-1,2,3,4-tetrahydroquinazolin-2-one
approved: f
ligand name: compound 11h [PMID: 29808961]
type: SyntheticOrganicLigand

lumefantrine
isomeric SMILES: CCCCN(CC(c1cc(Cl)cc2c1c1ccc(cc1/C/2=C/c1ccc(cc1)Cl)Cl)O)CCCC
in ch i key: DYLGFOYVTXJFJP-MYYYXRDXSA-N
in ch i: InChI=1S/C30H32Cl3NO/c1-3-5-13-34(14-6-4-2)19-29(35)28-18-23(33)17-27-25(15-20-7-9-21(31)10-8-20)26-16-22(32)11-12-24(26)30(27)28/h7-12,15-18,29,35H,3-6,13-14,19H2,1-2H3/b25-15-
comment: Lumefantrine belongs to the aryl amino alcohols, a chemical class of antimalarial compounds that includes <Ligand id=2510/>, <Ligand id=4252/> and <Ligand id=10019/>. Lumefantrine is a racemic mixture, with PubChem listing 9 stereoisotopes. The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
iupac name: 2-(dibutylamino)-1-[(9Z)-2,7-dichloro-9-[(4-chlorophenyl)methylidene]fluoren-4-yl]ethanol
xref: CHEMBL38827
synonym: benflumetol
approved: t
ligand name: lumefantrine
type: SyntheticOrganicLigand

PSB-17365
canonical SMILES: Brc1ccc(cc1)CCNc1cc(=O)[nH]c(=O)[nH]1
isomeric SMILES: Brc1ccc(cc1)CCNc1cc(=O)[nH]c(=O)[nH]1
in ch i key: XGNIAOMGYRRHNY-UHFFFAOYSA-N
in ch i: InChI=1S/C12H12BrN3O2/c13-9-3-1-8(2-4-9)5-6-14-10-7-11(17)16-12(18)15-10/h1-4,7H,5-6H2,(H3,14,15,16,17,18)
comment: PSB-17365 is the most potent of a series of synthetic GPR84 agonists reported by Pillaiyar et al. (2018) <Reference id=34636/>. This compound is a stable experimental tool that is suitable for in vitro and in vivo studies designed to further clarify the physiological role(s) of GPR84 and examine its therapeutic potential.
iupac name: 6-{[2-(4-bromophenyl)ethyl]amino}-1,2,3,4-tetrahydropyrimidine-2,4-dione
synonym: compound 48 [Pillaiyar et al., 2018]
synonym: PSB17365
approved: f
ligand name: PSB-17365
type: SyntheticOrganicLigand

ML193
in ch i key: HTSLEZOTMYUPLU-UHFFFAOYSA-N
in ch i: InChI=1S/C28H25N5O4S/c1-16-13-17(2)26-22(14-16)23(15-25(31-26)24-7-5-6-12-29-24)27(34)30-20-8-10-21(11-9-20)38(35,36)33-28-18(3)19(4)32-37-28/h5-15,33H,1-4H3,(H,30,34)
comment: Selective GPR55 antagonist.
iupac name: N-[4-[(3,4-dimethyl-1,2-oxazol-5-yl)sulfamoyl]phenyl]-6,8-dimethyl-2-pyridin-2-ylquinoline-4-carboxamide
synonym: ML-193
synonym: ML 193
approved: f
ligand name: ML193
type: SyntheticOrganicLigand

squarunkin A
in ch i key: ZKITWOVRRSBKFG-UHFFFAOYSA-N
in ch i: InChI=1S/C25H32F3N5O4/c1-2-37-24(36)33-9-6-18(7-10-33)30-21-20(22(34)23(21)35)29-8-11-31-12-14-32(15-13-31)19-5-3-4-17(16-19)25(26,27)28/h3-5,16,18,29-30H,2,6-15H2,1H3
comment: Squarunkin A is a small molecule inhibitor of the interaction of N-terminally myristoylated Src kinase with the lipid binding chaperone protein UNC119 <Reference id=35109/>. Squarunkin A modulates Src kinases using a molecular mechanism that is distinct from classical kinase inhibitors which directly target enzymatic activity.
iupac name: ethyl 4-({3,4-dioxo-2-[(2-{4-[3-(trifluoromethyl)phenyl]piperazin-1-yl}ethyl)amino]cyclobut-1-en-1-yl}amino)piperidine-1-carboxylate
synonym: compound 3j [PMID: 28471079]
approved: f
ligand name: squarunkin A
type: SyntheticOrganicLigand

compound 3a [Pipionne et al, 2018]
canonical SMILES: Cc1nn(c(c1c1ccc(c(c1)Cl)Cl)N)C(=O)C
isomeric SMILES: Cc1nn(c(c1c1ccc(c(c1)Cl)Cl)N)C(=O)C
in ch i key: HJXDCOSNNVYHCY-UHFFFAOYSA-N
in ch i: InChI=1S/C12H11Cl2N3O/c1-6-11(12(15)17(16-6)7(2)18)8-3-4-9(13)10(14)5-8/h3-5H,15H2,1-2H3
comment: Compound 3a was identified and optimised in a hit-to-lead study to identify inhibitors of the non-canonical NF-κB cascade in tumour cells <Reference id=35107/>. 3a inhibits activity of the NF-κB-inducing kinase, NIK (MAP3K14), and is a representative example of a series of compounds with NIK selectivity, the most potent of which was 3e (biochemical IC50 2.9 μM).
iupac name: 1-[5-amino-4-(3,4-dichlorophenyl)-3-methyl-1H-pyrazol-1-yl]ethan-1-one
approved: f
ligand name: compound 3a [Pipionne et al, 2018]
type: SyntheticOrganicLigand

NIK SMI1
canonical SMILES: COc1cc(nc(c1)c1cccc(c1)C#CC1(O)CCN(C1=O)C)C(=O)N
isomeric SMILES: COc1cc(nc(c1)c1cccc(c1)C#C[C@]1(O)CCN(C1=O)C)C(=O)N
in ch i key: LQSHXYHWYGKAMX-FQEVSTJZSA-N
in ch i: InChI=1S/C20H19N3O4/c1-23-9-8-20(26,19(23)25)7-6-13-4-3-5-14(10-13)16-11-15(27-2)12-17(22-16)18(21)24/h3-5,10-12,26H,8-9H2,1-2H3,(H2,21,24)/t20-/m0/s1
comment: NIK SMI1 is a selective inhibitor of the NF-κB-inducing kinase, NIK (MAP3K14) <Reference id=35106/>. NIK is a kinase that operates downstream of several TNF family receptors, including BAFF (TNFRSF13C), TWEAK (TNFRSF12A), CD40 (TNFRSF5), and OX40 (TNFRSF4), and which mediates non-canonical NF-κB signaling. Inhibition of NIK recapitulates the inhibition of BAFF that is observed for example using the anti-BAFF, SLE approved biologic <Ligand id=6887/>. The compound has no effect on canonical NF-κB signaling.
iupac name: 6-(3-{2-[(3R)-3-hydroxy-1-methyl-2-oxopyrrolidin-3-yl]ethynyl}phenyl)-4-methoxypyridine-2-carboxamide
approved: f
ligand name: NIK SMI1
type: SyntheticOrganicLigand

atabecestat
in ch i key: VLLFGVHGKLDDLW-SFHVURJKSA-N
in ch i: InChI=1S/C18H14FN5OS/c1-18(6-7-26-17(21)24-18)13-8-12(3-4-14(13)19)23-16(25)15-5-2-11(9-20)10-22-15/h2-8,10H,1H3,(H2,21,24)(H,23,25)/t18-/m0/s1
comment: JNJ-54861911 was originally discovered at Shionogi in 2008 as a BACE1 inhibitor. Clinical development was progressed by Janssen as atabecestat <Reference id=41438/>. The compound is orally active with good brain penetration and low P-gp substrate characteristic, which reflects in vivo Aβ reduction in brain and CSF for rat, monkey, and dog. However, serious elevations of liver enzymes were observed in the Phase 2b/3 study patients, causing the trial to be stopped in May 2018. The Phase 1 results were published in Sept 2018 <Reference id=36160/>.
iupac name: N-[3-[(4S)-2-amino-4-methyl-1,3-thiazin-4-yl]-4-fluorophenyl]-5-cyanopyridine-2-carboxamide
synonym: JNJ-54861911
synonym: JNJ-54861911-AAA
synonym: RSC-385896
approved: f
ligand name: atabecestat
type: SyntheticOrganicLigand

trifarotene
in ch i key: MFBCDACCJCDGBA-UHFFFAOYSA-N
in ch i: InChI=1S/C29H33NO4/c1-29(2,3)25-19-23(10-12-26(25)30-14-4-5-15-30)24-18-22(11-13-27(24)34-17-16-31)20-6-8-21(9-7-20)28(32)33/h6-13,18-19,31H,4-5,14-17H2,1-3H3,(H,32,33)
comment: Trifarotene (CD5789) is a RARγ-selective agonist that was developed as a topical anti-acne therapeutic <Reference id=35100/><Reference id=38373/><Reference id=38374/>.
iupac name: 4-[3-(3-tert-butyl-4-pyrrolidin-1-ylphenyl)-4-(2-hydroxyethoxy)phenyl]benzoic acid
xref: CHEMBL3707313
synonym: Aklief®
synonym: CD5789
synonym: compound 15b [PMID: 29706423]
approved: t
ligand name: trifarotene
type: SyntheticOrganicLigand

Compound 12 [PMID:28626832]
canonical SMILES: CN(c1nc(nc2c1cccc2)N1CCCC1)C
isomeric SMILES: CN(c1nc(nc2c1cccc2)N1CCCC1)C
in ch i key: VONNLDQOEHSECV-UHFFFAOYSA-N
in ch i: InChI=1S/C14H18N4/c1-17(2)13-11-7-3-4-8-12(11)15-14(16-13)18-9-5-6-10-18/h3-4,7-8H,5-6,9-10H2,1-2H3
comment: This work describes an approach to identify β-secretase 1 (BACE1) fragment binders. Assays, NMR and crystallographic studies with the soluble domain of BACE1 identified a unique binding mode for compound 12, a fragment that still occupies the active site while not making any interactions with catalytic Aspartic acid residues <Reference id=34393/>. The very low IC50 of 0.5 mM is a consequence of being a fragment but this is unusual in having a PDB crystal structure 5MXD showing the novel active site interactions.
iupac name: N,N-dimethyl-2-pyrrolidin-1-ylquinazolin-4-amine
approved: f
ligand name: Compound 12 [PMID:28626832]
type: SyntheticOrganicLigand

compound 20f [PMID: 28520415]
in ch i key: ZUQSHQGUCXJKSV-QFIPXVFZSA-N
in ch i: InChI=1S/C32H40N8OS/c1-20(2)16-38(5)25-9-11-39(12-10-25)17-23-7-6-8-24(13-23)29-26(14-28-40(32(29)41)21(3)18-42-28)22(4)37-31-27(15-33)30(34)35-19-36-31/h6-8,13-14,18-20,22,25H,9-12,16-17H2,1-5H3,(H3,34,35,36,37)/t22-/m0/s1
comment: Compound 20f [PMID: 28520415] is reported as a selective inhibitor of PI3Kδ that was specifically designed as an inhalation drug with potential immunomodulatory effects, and which could be effective as a treatment of airway inflammation <Reference id=35099/>. It has limited oral bioavailability and systemic exposure, but is retained in lung tissue in vivo following intratracheal delivery.
iupac name: 4-amino-6-{[(1S)-1-{3-methyl-6-[3-({4-[methyl(2-methylpropyl)amino]piperidin-1-yl}methyl)phenyl]-5-oxo-5H-[1,3]thiazolo[3,2-a]pyridin-7-yl}ethyl]amino}pyrimidine-5-carbonitrile
approved: f
ligand name: compound 20f [PMID: 28520415]
type: SyntheticOrganicLigand

compound 3 [PMID: 29633584]
in ch i key: CAGSRYBLIZYFGG-UHFFFAOYSA-N
in ch i: InChI=1S/C17H13N3O6/c1-25-14-12(7-19-17(20-14)26-2)8-5-11-9(15(21)22)3-4-10(16(23)24)13(11)18-6-8/h3-7H,1-2H3,(H,21,22)(H,23,24)
comment: This compound 3 is a lead chemical scaffold for the further development of lysine demethylase 6B (KDM6B, also known as JMJD3 and Jumonji D3) inhibitors. JMJD3 is an inducible enzyme, that along with ubiquitously transcribed X chromosome tetratricopeptide repeat protein (UTX), forms the KDM6 subfamily of histone modifying enzymes, which catalyze the demethylation of lysine 27 on histone H3 (H3K27). H3K27 demethylases are involved in maintaining the epigenetic transcriptional state in replicating and postmitotic cells. Prior to the discovery of compound 3, <Ligand id=7027/> and its derivatives were the only selective KDM6 inhibitors to be reported <Reference id=24169/><Reference id=35093/>. Compound 3 is suitable for investigating the role of JMJD3 in normal tissues and in tissues that are altered by pathological conditions, such as cancer and inflammation.
iupac name: 3-(2,4-dimethoxypyrimidin-5-yl)quinoline-5,8-dicarboxylic acid
approved: f
ligand name: compound 3 [PMID: 29633584]
type: SyntheticOrganicLigand

artemotil
canonical SMILES: CCOC1OC2OC3(C)CCC4C2(C(C1C)CCC4C)OO3
in ch i key: NLYNIRQVMRLPIQ-XQLAAWPRSA-N
in ch i: InChI=1S/C17H28O5/c1-5-18-14-11(3)13-7-6-10(2)12-8-9-16(4)20-15(19-14)17(12,13)22-21-16/h10-15H,5-9H2,1-4H3/t10-,11-,12+,13+,14+,15-,16-,17-/m1/s1
comment: Artemotil is a semisynthetic derivative of <Ligand id=9954/>, a natural product isolated from the qinghao or sweet wormwood plant (Artemisia annua). It contains an unusual endoperoxide bridge, believed to be responsible for the antimalarial activity of artemisinin and its derivatives. Artemotil is a prodrug that is converted to the active metabolite <Ligand id=9957/> (dihydroartemisinin). The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
iupac name: (1R,4S,5R,8S,9R,10S,12R,13R)-10-ethoxy-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadecane
xref: CHEMBL301267
synonym: β-arteether
approved: f
ligand name: artemotil
type: NaturalProductLigand

artenimol
canonical SMILES: OC1OC2OC3(C)CCC4C2(C(C1C)CCC4C)OO3
in ch i key: BJDCWCLMFKKGEE-ISOSDAIHSA-N
in ch i: InChI=1S/C15H24O5/c1-8-4-5-11-9(2)12(16)17-13-15(11)10(8)6-7-14(3,18-13)19-20-15/h8-13,16H,4-7H2,1-3H3/t8-,9-,10+,11+,12+,13-,14-,15-/m1/s1
comment: Artenimol is the active metabolite of <Ligand id=9954/> and all artemisinin-derived antimalarial compounds. We show one representation of artenimol here. As with other natural products, there are alternative chemical structures due to the complex stereochemistry. The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
iupac name: (3r,5as,6r,8as,9r,10s,12r,12ar)-decahydro-3,6,9-trimethyl-3,12-epoxy-12h-pyrano[4,3-j][1,2]benzodioxepin-10-ol
synonym: dihydroartemisinin
synonym: DHA
synonym: GNF-Pf-5634
approved: t
ligand name: artenimol
type: NaturalProductLigand

artesunate
in ch i key: FIHJKUPKCHIPAT-AHIGJZGOSA-N
in ch i: InChI=1S/C19H28O8/c1-10-4-5-13-11(2)16(23-15(22)7-6-14(20)21)24-17-19(13)12(10)8-9-18(3,25-17)26-27-19/h10-13,16-17H,4-9H2,1-3H3,(H,20,21)/t10-,11-,12+,13+,16-,17-,18-,19-/m1/s1
comment: Artesunate is a semisynthetic derivative of <Ligand id=9954/>, a natural product isolated from the qinghao or sweet wormwood plant (Artemisia annua). It contains an unusual endoperoxide bridge, believed to be responsible for the antimalarial activity of artemisinin and its derivatives. Artesunate is a prodrug that is converted to the active metabolite <Ligand id=9957/> (dihydroartemisinin). The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
iupac name: 4-oxo-4-[[(1R,4S,5R,8S,9R,10S,12R,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadecan-10-yl]oxy]butanoic acid
xref: CHEMBL361497
approved: t
ligand name: artesunate
type: SyntheticOrganicLigand

artemether
canonical SMILES: COC1OC2OC3(C)CCC4C2(C(C1C)CCC4C)OO3
in ch i key: SXYIRMFQILZOAM-HVNFFKDJSA-N
in ch i: InChI=1S/C16H26O5/c1-9-5-6-12-10(2)13(17-4)18-14-16(12)11(9)7-8-15(3,19-14)20-21-16/h9-14H,5-8H2,1-4H3/t9-,10-,11+,12+,13+,14-,15-,16-/m1/s1
comment: Artemether is a semisynthetic derivative of <Ligand id=9954/>, a natural product isolated from the qinghao or sweet wormwood plant (Artemisia annua). Synthesis yields two crystalline anomers, α- and β-artemether, the latter predominates and is marginally more active <Reference id=35320/>. Artemether is a prodrug that is converted to the active metabolite <Ligand id=9957/> (dihydroartemisinin). The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
iupac name: (1R,4S,5R,8S,9R,10S,12R,13R)-10-methoxy-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadecane
xref: CHEMBL566534
synonym: beta-artemether
synonym: β-artemether
approved: t
ligand name: artemether
type: NaturalProductLigand

artemisinin
canonical SMILES: O=C1OC2OC3(C)CCC4C2(C(C1C)CCC4C)OO3
in ch i key: BLUAFEHZUWYNDE-NNWCWBAJSA-N
in ch i: InChI=1S/C15H22O5/c1-8-4-5-11-9(2)12(16)17-13-15(11)10(8)6-7-14(3,18-13)19-20-15/h8-11,13H,4-7H2,1-3H3/t8-,9-,10+,11+,13-,14-,15-/m1/s1
comment: Artemisinin is a sesquiterpene lactone with an unusual endoperoxide bridge, believed to be responsible for the antimalarial activity of the compound. It is a natural product, isolated from the qinghao or sweet wormwood plant (Artemisia annua) and used in Chinese traditional medicine to treat fever. Artemisinin is a prodrug that is converted to the active metabolite <Ligand id=9957/> (dihydroartemisinin). We show one representation of artemisinin here. As with other natural products, there are alternative chemical structures due to the complex stereochemistry. The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
iupac name: (1R,4S,5R,8S,9R,12S,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadecan-10-one
xref: CHEMBL269671
synonym: qinghaosu
approved: f
ligand name: artemisinin
type: NaturalProductLigand

avatrombopag
in ch i key: OFZJKCQENFPZBH-UHFFFAOYSA-N
comment: Avatrombopag is a second generation, small molecule, orally administered thrombopoietin receptor agonist <Reference id=35081/>. It was discovered through its ability to mimic the action of endogenous thrombopoietin which is the primary physiological regulator of normal platelet production. The pharmacokinetics, pharmacodynamics, pharmacogenomics, safety, and tolerability of avatrombopag were reported by Nomoto et al. in 2017 <Reference id=35082/>.
iupac name: 1-[3-chloro-5-[[4-(4-chlorothiophen-2-yl)-5-(4-cyclohexylpiperazin-1-yl)-1,3-thiazol-2-yl]carbamoyl]pyridin-2-yl]piperidine-4-carboxylic acid
xref: CHEMBL2103883
synonym: Doptelet®
synonym: YM477
synonym: AKR-501
synonym: E5501
approved: t
ligand name: avatrombopag
type: SyntheticOrganicLigand

primaquine
canonical SMILES: NCCCC(Nc1cc(OC)cc2c1nccc2)C
isomeric SMILES: NCCCC(Nc1cc(OC)cc2c1nccc2)C
in ch i key: INDBQLZJXZLFIT-UHFFFAOYSA-N
in ch i: InChI=1S/C15H21N3O/c1-11(5-3-7-16)18-14-10-13(19-2)9-12-6-4-8-17-15(12)14/h4,6,8-11,18H,3,5,7,16H2,1-2H3
comment: Primaquine is a synthetic, 8-aminoquinoline derivative that has potent antimalarial activity. The approved drug is a racemic mixture and we show the chemical structure without stereochemistry to represent the mixture. The non-isomeric structure is also represented in the PubChem, ChEMBL and ChEBI entries listed in the links table below, while the two enantiomers forming the racemate are represented by PubChem CID 3044368 and PubChem CID 3044369. The marketed formulations contain primaquine phosphate (PubChem CID 6135). The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
iupac name: N-(6-methoxyquinolin-8-yl)pentane-1,4-diamine
xref: CHEMBL506
approved: t
ligand name: primaquine
type: SyntheticOrganicLigand

nitroglycerin
canonical SMILES: [O-][N+](=O)OC(CO[N+](=O)[O-])CO[N+](=O)[O-]
isomeric SMILES: [O-][N+](=O)OC(CO[N+](=O)[O-])CO[N+](=O)[O-]
in ch i key: SNIOPGDIGTZGOP-UHFFFAOYSA-N
in ch i: InChI=1S/C3H5N3O9/c7-4(8)13-1-3(15-6(11)12)2-14-5(9)10/h3H,1-2H2
comment: Nitroglycerin acts as a vasodilator.
iupac name: 1,3-dinitrooxypropan-2-yl nitrate
xref: CHEMBL730
synonym: Rectogesic®
synonym: Nitrol
synonym: Rectiv
synonym: Tridil
synonym: Nitronal
synonym: Nitromist
synonym: Nitrostat
synonym: glyceryl trinitrate
synonym: Minitran®
synonym: Glytrin®
approved: t
ligand name: nitroglycerin
type: SyntheticOrganicLigand

WAY-316606
in ch i key: ITBGJNVZJBVPLJ-UHFFFAOYSA-N
comment: WAY-316606 was originally identified as a small molecule inhibitor of the endogenous Wnt antagonist <Ligand id=3691/> (a.k.a. SARP2), as a novel anabolic agent for the treatment of osteoporosis or other bone-related disorders <Reference id=35015/>. Mechanistically it binds to sFRP-1 and out-competes Wnt binding to sFRP-1, thereby releasing Wnt for binding to the LRP-frizzled receptor complex, an effect that ultimately promotes canonical Wnt signaling and increases anabolic bone formation <Reference id=35016/>. Subsequent study has found that WAY-316606 may have potential as a hair re-growth strategy with potential clinical relevance for treatment of human hair loss disorders <Reference id=35017/>. WAY-316606 was found to enhance hair shaft production, hair shaft keratin expression, and reduce spontaneous hair follicle regression in ex vivo human scalp explants, via a canonical Wnt/β-catenin-dependent mechanism.
iupac name: 5-(benzenesulfonyl)-N-piperidin-4-yl-2-(trifluoromethyl)benzenesulfonamide
xref: CHEMBL495575
synonym: compound 1 [PMID: 19072540]
approved: f
ligand name: WAY-316606
type: SyntheticOrganicLigand

MM-433593
in ch i key: RIKZRSJVZWKHNX-UHFFFAOYSA-N
in ch i: InChI=1S/C25H22ClN3O3/c1-15-4-9-21-20(12-15)23(16(2)29(21)14-17-5-7-18(26)8-6-17)24(30)25(31)28-19-10-11-27-22(13-19)32-3/h4-13H,14H2,1-3H3,(H,27,28,31)
comment: The authors of this study claim MM-433593 is a oral, potent and selective inhibitor of fatty acid amide hydrolase-1 (FAAH1) with potential for treatment of pain, inflammation, and other disorders <Reference id=35013/>.
iupac name: 2-[1-[(4-chlorophenyl)methyl]-2,5-dimethylindol-3-yl]-N-(2-methoxypyridin-4-yl)-2-oxoacetamide
synonym: MM433593
approved: f
ligand name: MM-433593
type: SyntheticOrganicLigand

PF-06751979
in ch i key: JQUCWIWWWKZNCS-LESHARBVSA-N
comment: This recent (April 2018) Pfizer BACE1 inhibitor for Alzheimer's disease showed brain penetration, potent in vivo efficacy and broad selectivity over related aspartyl proteases including BACE2 <Reference id=35012/>.
iupac name: N-[2-[(4aR,6S,8aR)-2-benzamido-6-methyl-4a,5,6,8-tetrahydro-4H-pyrano[3,4-d][1,3]thiazin-8a-yl]-1,3-thiazol-4-yl]-5-(difluoromethoxy)pyridine-2-carboxamide
synonym: PF06751979
synonym: compound 64 [PMID: 29613789]
approved: f
ligand name: PF-06751979
type: SyntheticOrganicLigand

AZD0156
in ch i key: AOTRIQLYUAFVSC-UHFFFAOYSA-N
in ch i: InChI=1S/C26H31N5O3/c1-29(2)11-4-12-34-24-8-6-19(16-28-24)18-5-7-22-21(15-18)25-23(17-27-22)30(3)26(32)31(25)20-9-13-33-14-10-20/h5-8,15-17,20H,4,9-14H2,1-3H3
comment: AZD0156 is a potent and selective inhibitor of ATM serine/threonine kinase from AstraZeneca that is being developed for anti-cancer potential <Reference id=35008/>. It potentiates the efficacy of <Ligand id=6823/> and <Ligand id=7519/> in disease relevant mouse models and is currently undergoing clinical evaluation.
iupac name: 8-[6-[3-(dimethylamino)propoxy]pyridin-3-yl]-3-methyl-1-(oxan-4-yl)imidazo[4,5-c]quinolin-2-one
synonym: compound 64 [PMID: 29683659]
approved: f
ligand name: AZD0156
type: SyntheticOrganicLigand

TAS05567
in ch i key: ATERGQQFFHVNOJ-LSDHHAIUSA-N
in ch i: InChI=1S/C21H29N9O2/c1-11-7-13(8-12-9-30(21(2,3)4)29-16(11)12)24-19-17(18(23)31)27-28-20(26-19)25-15-5-6-32-10-14(15)22/h7-9,14-15H,5-6,10,22H2,1-4H3,(H2,23,31)(H2,24,25,26,28)/t14-,15+/m0/s1
comment: TAS05567 is a selective spleen tyrosine kinase (Syk) inhibitor and potential therapeutic candidate for treating humoral immune-mediated inflammatory conditions such as autoimmune and allergic diseases <Reference id=35018/>.
iupac name: 3-[(3-aminooxan-4-yl)amino]-5-[(2-tert-butyl-7-methyl-2H-indazol-5-yl)amino]-1,2,4-triazine-6-carboxamide
approved: f
ligand name: TAS05567
type: SyntheticOrganicLigand

LW106
canonical SMILES: ON=C(c1nonc1N)N1Cc2c(C1)cccc2
isomeric SMILES: O/N=C(/c1nonc1N)/N1Cc2c(C1)cccc2
in ch i key: QHVIXMMITPHBSL-ACCUITESSA-N
in ch i: InChI=1S/C11H11N5O2/c12-10-9(14-18-15-10)11(13-17)16-5-7-3-1-2-4-8(7)6-16/h1-4,17H,5-6H2,(H2,12,15)/b13-11+
comment: LW106 is a novel small-molecule IDO1 inhibitor <Reference id=35001/>. In xenograft models LW106 dose-dependently inhibited tumour outgrowth more effectively than the existing IDO1 inhibitor <Ligand id=8221/>, despite epacadostat being a more potent inhibitor in vitro <Reference id=27054/>. LW106 promoted tumour infiltration by proliferative Teff cells and reduced recruitment of proliferative Treg cells, endothelial cells and cancer-associated fibroblasts. It also reduced tumour resident cancer stem cell numbers.
iupac name: 4-[(E)-(2,3-dihydro-1H-isoindol-2-yl)(hydroxyimino)methyl]-1,2,5-oxadiazol-3-amine
approved: f
ligand name: LW106
type: SyntheticOrganicLigand

pCXCL8-1aa
in ch i key: WAKZDRBORDWUSJ-NXCVNOGKSA-N
in ch i: InChI=1S/C53H88N16O17/c1-28(2)24-36(66-50(83)37(25-30-12-5-4-6-13-30)67-47(80)32(14-7-9-21-54)63-44(77)31(56)17-19-41(72)73)49(82)65-33(15-8-10-22-55)46(79)64-34(16-11-23-60-53(58)59)45(78)61-29(3)43(76)62-35(18-20-42(74)75)48(81)68-38(26-40(57)71)51(84)69-39(27-70)52(85)86/h4-6,12-13,28-29,31-39,70H,7-11,14-27,54-56H2,1-3H3,(H2,57,71)(H,61,78)(H,62,76)(H,63,77)(H,64,79)(H,65,82)(H,66,83)(H,67,80)(H,68,81)(H,69,84)(H,72,73)(H,74,75)(H,85,86)(H4,58,59,60)/t29-,31-,32-,33-,34-,35-,36-,37-,38-,39-/m0/s1
comment: This is a small peptide that mimics the glycosaminoglycan (GAG) binding domain found in the C-terminal α helix of the CXCL8 cytokine <Reference id=34984/>. It competes with CXCL8 for binding to GAGs, and by interfering in this interaction, reduces CXCL8-mediated inflammatory responses (leukocyte activation and extravasation to inflammatory sites). The archetypal GAG-binding motif on CXC chemokines takes the form XBBBXXBX (where B = a basic amino acid and X = any nonbasic amino acid) <Reference id=34985/>. The reference article also describes small peptides that interfere with CCL5 and CXCL12γ GAG binding <Reference id=34984/>. Chemokine interactions with GAGs localise the chemokines around cell surfaces and the extracellular matrix. This provides a guidance mechanism for leukocyte migration <Reference id=34987/>. Disrupting this guidance mechanism is predicted to produce anti-inflammatory effects, by reducing the ability of pro-inflammatory cells to migrate to sites of inflammation in response to cytokine signals.
approved: f
ligand name: pCXCL8-1aa
type: PeptideLigand

compound 7d [PMID: 29672049]
in ch i key: SAEGVASGMTZGFI-AQYVVDRMSA-N
in ch i: InChI=1S/C27H38N8O/c28-20-7-11-22(12-8-20)31-27-32-25(24-26(33-27)35(18-29-24)23-3-1-2-4-23)30-21-9-5-19(6-10-21)17-34-13-15-36-16-14-34/h5-6,9-10,18,20,22-23H,1-4,7-8,11-17,28H2,(H2,30,31,32,33)/t20-,22-
comment: Compound 7d is a FLT3 inhibitor <Reference id=34981/>. It was identified as a lead compound in a medicinal chemistry study to find novel chemical scaffolds that offer improved FLT3 inhibition, and that provide compounds with potential clinical oncology therapeutic value for FLT3-driven cancers. Similar levels of inhibition of wild type and D835Y-mutated FLT3 enzymes suggests that compound 7d is a Type I (ATP binding site) kinase inhibitor. In comparison to <Ligand id=5658/>, a single dose of compound 7d produces a longer-lived inhibition of FLT3 and STAT5 phosphorylation in xenograft mice.
iupac name: 9-cyclopentyl-N6-[4-(morpholin-4-ylmethyl)phenyl]-N2-[(1r,4r)-4-aminocyclohexyl]-9H-purine-2,6-diamine
approved: f
ligand name: compound 7d [PMID: 29672049]
type: SyntheticOrganicLigand

GKT136901
in ch i key: DNKYHHFCPXKFIY-UHFFFAOYSA-N
in ch i: InChI=1S/C19H15ClN4O2/c1-12-18-15(10-17(25)23(12)11-13-6-4-5-9-21-13)22-24(19(18)26)16-8-3-2-7-14(16)20/h2-10,22H,11H2,1H3
comment: GKT136901 was identified as a lead compound in a high-throughput screening and medicinal chemistry campaign that was designed to identify novel NOX4-selective inhibitors <Reference id=34963/>. It is an orally active compound that is suitable for investigating the preclinical potential of NOX4 inhibitors for the treatment of fibrotic diseases and cancers in which NOX4 activity has been implicated.
iupac name: 2-(2-chlorophenyl)-4-methyl-5-(pyridin-2-ylmethyl)-1H-pyrazolo[4,3-c]pyridine-3,6-dione
xref: CHEMBL1276946
synonym: compound 67 [PMID: 20942471]
synonym: GKT-136901
synonym: GKT 136901
approved: f
ligand name: GKT136901
type: SyntheticOrganicLigand

compound 87 [PMID: 20942471]
in ch i key: QEBYEVQKHRUYPE-UHFFFAOYSA-N
in ch i: InChI=1S/C25H24ClN7O2/c1-30(14-17-6-5-10-27-13-17)16-22-24-20(12-23(34)32(22)15-18-9-11-31(2)28-18)29-33(25(24)35)21-8-4-3-7-19(21)26/h3-13,29H,14-16H2,1-2H3
comment: This is one of a series of compounds identified in a medicinal chemistry campaign designed to discover drug-like inhibitors of NADPH oxidase isoform 4 (NOX4) <Reference id=34963/>. This compound, 87, is a nanomolar inhibitor of NOX-driven reactive oxygen species (ROS) production in cell free assays. It is orally active, and is suitable for in vivo studies.
iupac name: 2-(2-chlorophenyl)-5-[(1-methylpyrazol-3-yl)methyl]-4-[[methyl(pyridin-3-ylmethyl)amino]methyl]-1H-pyrazolo[4,3-c]pyridine-3,6-dione
approved: f
ligand name: compound 87 [PMID: 20942471]
type: SyntheticOrganicLigand

NSC 780521
canonical SMILES: [O-][N+](=O)c1cccc2c1c1c([I-]2)cccc1[N+](=O)[O-]
isomeric SMILES: [O-][N+](=O)c1cccc2c1c1c([I-]2)cccc1[N+](=O)[O-]
in ch i key: NBIXKUWRZRFYBQ-UHFFFAOYSA-N
in ch i: InChI=1S/C12H6IN2O4/c16-14(17)9-5-1-3-7-11(9)12-8(13-7)4-2-6-10(12)15(18)19/h1-6H/q-1
comment: NSC 780521 is an experimental DUOX2-selective inhibitor <Reference id=34954/>. It shows anti-proliferative activity against NOX-driven tumour cells. The compound is delivered as a bromide salt in a 1:1 ratio.
iupac name: 1,9-dinitro-dibenziodolium
synonym: NSC-780521
synonym: NSC780521
synonym: compound 521 [PMID: 28709950]
approved: f
ligand name: NSC 780521
type: SyntheticOrganicLigand

setanaxib
in ch i key: RGYQPQARIQKJKH-UHFFFAOYSA-N
in ch i: InChI=1S/C21H19ClN4O2/c1-24(2)14-8-6-7-13(11-14)20-19-16(12-18(27)25(20)3)23-26(21(19)28)17-10-5-4-9-15(17)22/h4-12,23H,1-3H3
comment: Setanaxib (GKT137831) is an investigational dual NOX1/NOX4 inhibitor <Reference id=34955/>. It has shown anti-inflammatory activity in models of liver fibrosis <Reference id=34955/> and retinopathy <Reference id=34956/>.
iupac name: 2-(2-chlorophenyl)-4-[3-(dimethylamino)phenyl]-5-methyl-1H-pyrazolo[4,3-c]pyridine-3,6-dione
synonym: GKT-137831
synonym: GKT831
synonym: GKT-831
synonym: GKT137831
approved: f
ligand name: setanaxib
type: SyntheticOrganicLigand

compound 7c [PMID: 22041175]
in ch i key: DISVMXDWAMMVLT-UHFFFAOYSA-N
in ch i: InChI=1S/C23H21ClN4O2/c24-17-9-4-5-10-19(17)28-23(30)22-18(25-28)13-21(29)27-12-6-11-26(15-20(22)27)14-16-7-2-1-3-8-16/h1-5,7-10,13,25H,6,11-12,14-15H2
comment: Compound 7c [PMID: 22041175] is a novel dual NOX4/NOX1 inhibitor that ameliorates bleomycin-induced pulmonary fibrosis, a finding which suggests that targeting the NOX4/1 activity as a potential molecular mechanism for the treatment of idiopathic pulmonary fibrosis <Reference id=34953/>.
iupac name: 10-benzyl-2-(2-chlorophenyl)-7,8,9,11-tetrahydro-3H-pyrazolo[4,5]pyrido[5,6-a][1,4]diazepine-1,5-dione
xref: CHEMBL1962788
approved: f
ligand name: compound 7c [PMID: 22041175]
type: SyntheticOrganicLigand

henatinib
isomeric SMILES: O[C@@H](CN1CCCc2c(C1=O)c(C)c([nH]2)/C=C/1/C(=O)Nc2c1cc(F)cc2)CN1CCOCC1
in ch i key: MCTXSDCWFQAGFS-UEXNTNOUSA-N
in ch i: InChI=1S/C25H29FN4O4/c1-15-22(12-19-18-11-16(26)4-5-20(18)28-24(19)32)27-21-3-2-6-30(25(33)23(15)21)14-17(31)13-29-7-9-34-10-8-29/h4-5,11-12,17,27,31H,2-3,6-10,13-14H2,1H3,(H,28,32)/b19-12-/t17-/m1/s1
comment: Henatinib is a kinase inhibitor with some selectivity for VEGFR2 (KDR). Discovery was reported by Cho et al. (2010), the same article that disclosed <Ligand id=7886/> <Reference id=26153/>. The name henatinib is linked to the structure of 'compound 25' in the article by Gu et al. (2010) that describes a method for detecting and quantifying henatinib maleate in rat plasma <Reference id=34941/>. Henatinib is a 'pseudo' INN, that takes the form of an INN for a kinase inhibitor, but has not been submitted to the World Health Organisation for ratification.
iupac name: 2-[(Z)-(5-fluoro-2-oxo-1H-indol-3-ylidene)methyl]-5-[(2R)-2-hydroxy-3-morpholin-4-ylpropyl]-3-methyl-1,6,7,8-tetrahydropyrrolo[3,2-c]azepin-4-one
xref: CHEMBL1277072
synonym: compound 25 [PMID: 21028894]
approved: f
ligand name: henatinib
type: SyntheticOrganicLigand

xiliertinib
in ch i key: HJXSISWJKLMCHI-FIFRQSLGSA-N
in ch i: InChI=1S/C25H28N6O2/c1-4-16-6-5-7-18(10-16)28-24-19-11-21(23(33-3)12-20(19)26-15-27-24)29-25(32)31-13-17-8-9-30(2)22(17)14-31/h1,5-7,10-12,15,17,19,22,24,28H,8-9,13-14H2,2-3H3,(H,29,32)/t17-,19?,22+,24?/m1/s1
comment: Xiliertinib (HMPL-309) is an ATP-competitive EGFR tyrosine kinase inhibitor that was developed for anticancer potential <Reference id=34937/>. Theliatinib appears to be a 'pseudo' INN, that uses the -tinib INN stem for tyrosine kinase inhibitors, but was not submitted to the World Health Organisation for ratification.
iupac name: (3aR,6aR)-N-[4-(3-ethynylanilino)-7-methoxy-4,4a-dihydroquinazolin-6-yl]-1-methyl-2,3,3a,4,6,6a-hexahydropyrrolo[2,3-c]pyrrole-5-carboxamide
synonym: HMPL-309
synonym: HMPL309
synonym: theliatinib
approved: f
ligand name: xiliertinib
type: SyntheticOrganicLigand

puquitinib
in ch i key: QUTFBURLXCODBH-UHFFFAOYSA-N
in ch i: InChI=1S/C17H15N7/c1-2-10-8-12(5-6-13(10)18-7-1)22-17-23-15-14(19-9-20-15)16(24-17)21-11-3-4-11/h1-2,5-9,11H,3-4H2,(H3,19,20,21,22,23,24)
comment: Puquitinib is an orally active, PI3 kinase inhibitor that induces autophagy by inhibiting the PI3K/AKT/mTOR signaling pathway. Puquitinib is selective for p110δ relative to other PI3K class I enzymes. It is a clinical lead developed for antitumour activity <Reference id=34934/>. Puquitinib is a 'pseudo' INN, that takes the form of an INN, but has not been submitted to the World Health Organisation for ratification.
iupac name: N'-cyclopropyl-N-quinolin-6-yl-7H-purine-2,6-diamine
synonym: XC-302
synonym: XC302
approved: f
ligand name: puquitinib
type: SyntheticOrganicLigand

cenisertib
in ch i key: KSOVGRCOLZZTPF-QMKUDKLTSA-N
in ch i: InChI=1S/C24H30FN7O/c1-14-11-17(5-6-19(14)32-9-7-31(2)8-10-32)28-24-27-13-18(25)23(30-24)29-21-16-4-3-15(12-16)20(21)22(26)33/h3-6,11,13,15-16,20-21H,7-10,12H2,1-2H3,(H2,26,33)(H2,27,28,29,30)/t15-,16+,20+,21-/m1/s1
comment: Cenisertib is an Aurora kinase A/B inhibitor that was developed for anti-cancer potential <Reference id=34931/>. We show the compound with chirality as specified by the IUPAC name submitted to the WHO for INN registration. It is compound 60a as claimed in patent WO2005118544A2 <Reference id=34930/>. Cenisertib has improved aqueous solubility compared to the dual inhibitor ABT-348 (<Ligand id=9914/>). Preclinical anti-proliferative efficacy of cenisertib has been demonstrated in a wide range of xenograft models <Reference id=34932/> and cell lines <Reference id=34933/>.
iupac name: (1S,2S,3R,4R)-3-[[5-fluoro-2-[3-methyl-4-(4-methylpiperazin-1-yl)anilino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide
xref: CHEMBL1614709
synonym: AS-703569
synonym: R-763
synonym: R763
synonym: compound 2 [PMID: 22695126]
synonym: AS703569
synonym: compound 60a [WO2005118544A2]
synonym: enantiomer E1 [WO2005118544A2]
approved: f
ligand name: cenisertib
type: SyntheticOrganicLigand

bentamapimod
in ch i key: XCPPIJCBCWUBNT-UHFFFAOYSA-N
in ch i: InChI=1S/C25H23N5O2S/c26-15-20(24-28-22-3-1-2-4-23(22)33-24)21-9-10-27-25(29-21)32-17-19-7-5-18(6-8-19)16-30-11-13-31-14-12-30/h1-10,20H,11-14,16-17H2
comment: Bentamapimod (a.k.a. PGL-5001 and AS602801) is novel and orally active Jun kinase inhibitor (JNK1= MAPK8 and JNK2= MAPK9). It has shown preclinical efficacy that may be applied to the treatment of endometriotic lesions <Reference id=34927/><Reference id=34928/>. It also inhibits cancer stem cells in vitro and in vivo <Reference id=34929/>. It was originally developed by Merck Seroneo (JNK-I AS602801) and then in-licensed by PregLem and re-named PGL5001 (PGL5 may also be used).
xref: CHEMBL3545213
synonym: AS-602801
synonym: AS602801
synonym: PGL-5001
synonym: PGL5001
approved: f
ligand name: bentamapimod
type: SyntheticOrganicLigand

pecazine
canonical SMILES: CN1CCCC(C1)CN1c2ccccc2Sc2c1cccc2
isomeric SMILES: CN1CCCC(C1)CN1c2ccccc2Sc2c1cccc2
in ch i key: CBHCDHNUZWWAPP-UHFFFAOYSA-N
in ch i: InChI=1S/C19H22N2S/c1-20-12-6-7-15(13-20)14-21-16-8-2-4-10-18(16)22-19-11-5-3-9-17(19)21/h2-5,8-11,15H,6-7,12-14H2,1H3
comment: Pecazine is a phenothiazine derivative that was historically used as an antipsychotic/tranquillizer, but use has replaced by newer drugs. Pecazine is also an allosteric inhibitor of MALT1 protease activity <Reference id=34155/>. It may be used experimentally as the acetate or hydrochloride.
iupac name: 10-[(1-methylpiperidin-3-yl)methyl]phenothiazine
xref: CHEMBL395110
synonym: nothiazine
synonym: mepazine
synonym: Pacatal
approved: t
ligand name: pecazine
type: SyntheticOrganicLigand

balamapimod
in ch i key: CVAKNHIXTWLGJO-UHFFFAOYSA-N
in ch i: InChI=1S/C30H32ClN7OS/c1-36-14-9-33-30(36)40-28-6-5-21(15-24(28)31)35-29-20(18-32)19-34-25-17-26(27(39-2)16-23(25)29)38-12-7-22(8-13-38)37-10-3-4-11-37/h5-6,9,14-17,19,22H,3-4,7-8,10-13H2,1-2H3,(H,34,35)
comment: Balamapimod (MKI-833) is an orally active, reversible kinase inhibitor that was developed for antineoplastic potential. It has a selectivity profile that includes inhibition of Ras/Raf/MEK/MAPK signalling pathway. The chemical structure is claimed as Example 11 in patent US20090062281A1 <Reference id=34926/>.
iupac name: 4-[3-chloro-4-(1-methylimidazol-2-yl)sulfanylanilino]-6-methoxy-7-(4-pyrrolidin-1-ylpiperidin-1-yl)quinoline-3-carbonitrile
xref: CHEMBL2104954
synonym: MKI-833
synonym: MKI833
synonym: MKI 833
approved: f
ligand name: balamapimod
type: SyntheticOrganicLigand

amcasertib
in ch i key: QDWKGEFGLQMDAM-UHFFFAOYSA-N
in ch i: InChI=1S/C31H33N5O2S/c1-5-36(6-2)15-14-32-30(38)28-19(3)26(33-20(28)4)17-24-23-16-22(12-13-25(23)34-29(24)37)27-18-39-31(35-27)21-10-8-7-9-11-21/h7-13,16-18,33H,5-6,14-15H2,1-4H3,(H,32,38)(H,34,37)
comment: Amcasertib (BBI503) is a first-in-class, orally active, cancer stemness kinase inhibitor has been developed by Boston Biomedical for potential anticancer activity <Reference id=34924/>. by targeting certain kinase enzymes it is reported to inhibit Nanog (NANOG; Q9H9S0) and other signalling pathways that control stem-cell replication, survival and differentiation. To date (April 2018) the only reports of BBI503 mechanism of action and clinical efficacy are in the form of meeting abstracts, and not in peer reviewed articles. Amcasertib is one of the chemical structures claimed in patent US8299106B2 <Reference id=34925/>, which were discussed as potential PDGFRα inhibitors therein.
iupac name: N-[2-(diethylamino)ethyl]-2,4-dimethyl-5-[[2-oxo-5-(2-phenyl-1,3-thiazol-4-yl)-1H-indol-3-ylidene]methyl]-1H-pyrrole-3-carboxamide
synonym: BBI503
synonym: BBI-503
approved: f
ligand name: amcasertib
type: SyntheticOrganicLigand

voruciclib
in ch i key: MRPGRAKIAJJGMM-OCCSQVGLSA-N
comment: Voruciclib (P1446A, or P1446A-05) is an orally active, non-selective CDK inhibitor that was developed for antineoplastic potential. Potent inhibition of CDK9, 4/6 and 1 by voruciclib is considered as a novel pro-apoptotic mechanism applicable to the treatment of malignant melanoma <Reference id=34919/> and to overcome resistance to Bcl-2 inhibition (e.g. by <Ligand id=8318/>) in B cell malignancies <Reference id=34920/><Reference id=34921/>. Use of voruciclib in combination with BRAF inhibitors for the treatment of malignant melanoma is claimed in patent US20160136132A1 <Reference id=34922/>. Preparation of pure (+)-trans enantiomer of the compound shown here, is claimed in patent WO2007148158A1 <Reference id=34923/>.
iupac name: 2-[2-chloro-4-(trifluoromethyl)phenyl]-5,7-dihydroxy-8-[(2R,3S)-2-(hydroxymethyl)-1-methylpyrrolidin-3-yl]chromen-4-one
synonym: P1446A
synonym: P1446A-05
approved: f
ligand name: voruciclib
type: SyntheticOrganicLigand

tucatinib
in ch i key: SDEAXTCZPQIFQM-UHFFFAOYSA-N
in ch i: InChI=1S/C26H24N8O2/c1-16-10-17(5-7-22(16)36-19-8-9-34-23(12-19)28-15-30-34)31-24-20-11-18(4-6-21(20)27-14-29-24)32-25-33-26(2,3)13-35-25/h4-12,14-15H,13H2,1-3H3,(H,32,33)(H,27,29,31)
comment: Tucatinib is an orally bioavailable ERBB2 (HER2) receptor tyrosine kinase inhibitor that was developed as a novel antineoplastic agent by Seattle Genetics <Reference id=39088/>. The chemical structure is claimed as Example 11 in Array Biopharma patent WO2007059257A2 <Reference id=34917/>, and was exemplified as ARRY-380 in the later patent WO2013056183A1 <Reference id=34918/>. Tucatinib contains a quinazoline core that is conserved in other tyrosine kinase inhibitors including <Ligand id=5692/>, <Ligand id=4920/>, and <Ligand id=4941/> <Reference id=39088/>. The INN tucatinib replaced the earlier INN irbinitinib that was associated with this chemical entity.
synonym: ARRY-380
synonym: ONT-380
synonym: Example 11 [WO2007059257A2]
synonym: Tukysa®
approved: t
ligand name: tucatinib
type: SyntheticOrganicLigand

tafetinib
isomeric SMILES: CCN(CCNC(=O)c1c(C)[nH]c2c1CCC/C/2=C/1/C(=O)Nc2c1cc(F)cc2)CC
in ch i key: KGSRYTUWXUESJK-FXBPSFAMSA-N
in ch i: InChI=1S/C24H29FN4O2/c1-4-29(5-2)12-11-26-23(30)20-14(3)27-22-16(20)7-6-8-17(22)21-18-13-15(25)9-10-19(18)28-24(21)31/h9-10,13,27H,4-8,11-12H2,1-3H3,(H,26,30)(H,28,31)/b21-17-
comment: Tafetinib (SIM010603) is an orally active inhibitor of multiple receptor tyrosine kinases (RTKs) that was developed as an antineoplatic agent <Reference id=34915/>. Some of its main targets are KIT, VEGFR, PDGFRβ, RET, and FLT3. It produces anti-angiogenic and anti-tumor effects in vitro and in vivo. Tafetinib is a 'pseudo' INN, that takes the form of an INN, but has not been submitted to the World Health Organisation for ratification.
iupac name: (7Z)-N-[2-(diethylamino)ethyl]-7-(5-fluoro-2-oxo-1H-indol-3-ylidene)-2-methyl-1,4,5,6-tetrahydroindole-3-carboxamide
xref: CHEMBL2180602
synonym: SIM010603
synonym: SIM 010603
synonym: SIM-010603
approved: f
ligand name: tafetinib
type: SyntheticOrganicLigand

sitravatinib
in ch i key: WLAVZAAODLTUSW-UHFFFAOYSA-N
comment: Sitravatinib (MGCD516) is an inhibitor of multiple receptor tyrosine kinases (RTKs) that was developed as an antineoplatic agent <Reference id=34914/>. It targets several RTKs (e.g. c-Met, PDGFR, c-Kit and IGF1-R) whose overexpression has been shown to drive sarcoma cell growth
iupac name: 1-N'-[3-fluoro-4-[2-[5-[(2-methoxyethylamino)methyl]pyridin-2-yl]thieno[3,2-b]pyridin-7-yl]oxyphenyl]-1-N-(4-fluorophenyl)cyclopropane-1,1-dicarboxamide
synonym: GCD516
synonym: GCD-516
synonym: GCD 516
synonym: MGCD516
approved: f
ligand name: sitravatinib
type: SyntheticOrganicLigand

selatinib
in ch i key: OAMVGUFHZPRXOM-UHFFFAOYSA-N
comment: Selatinib (L-2) is a dual EGFR/HER2 receptor tyrosine kinase inhibitor that was developed for anti-cancer potential <Reference id=34913/>. It is an anlogue of <Ligand id=5692/> and shares the same mechanism of action, but has an improved pharmacokinetic profile, with bioavailability at 187% of that of lapatinib. The tosylate salt form of selatinib is highly soluble. Selatinib is a 'pseudo' INN, that takes the form of an INN, but has not been submitted to the World Health Organisation for ratification.
iupac name: N-[3-chloro-4-[(3-fluorophenyl)methoxy]phenyl]-6-[5-[(2-methylsulfinylethylamino)methyl]furan-2-yl]quinazolin-4-amine
xref: CHEMBL3040548
approved: f
ligand name: selatinib
type: SyntheticOrganicLigand

savolitinib
in ch i key: XYDNMOZJKOGZLS-NSHDSACASA-N
in ch i: InChI=1S/C17H15N9/c1-11(12-3-4-15-18-5-6-25(15)10-12)26-17-16(22-23-26)19-8-14(21-17)13-7-20-24(2)9-13/h3-11H,1-2H3/t11-/m0/s1
comment: Savolitinib is a potent and selective, ATP-competitive mesenchymal-epithelial transition factor (c-Met) inhibitor that was designed for anti-cancer potential <Reference id=34912/>. In this discovery report it was called volitinib, but the designated INN is savolitinib. Research codes are HMPL-504 and AZD6094.
iupac name: 3-[(1S)-1-imidazo[1,2-a]pyridin-6-ylethyl]-5-(1-methylpyrazol-4-yl)triazolo[4,5-b]pyrazine
xref: CHEMBL3334567
synonym: volitinib
synonym: AZD6094
synonym: AZD-6094
synonym: HMPL-504
synonym: HMPL504
synonym: compound 28 [PMID: 25148209]
synonym: Orpathys®
approved: t
ligand name: savolitinib
type: SyntheticOrganicLigand

pexmetinib
in ch i key: LNMRSSIMGCDUTP-UHFFFAOYSA-N
in ch i: InChI=1S/C31H33FN6O3/c1-20-5-8-24(9-6-20)38-29(17-28(36-38)31(2,3)4)35-30(40)33-18-22-15-23(32)7-12-27(22)41-25-10-11-26-21(16-25)19-34-37(26)13-14-39/h5-12,15-17,19,39H,13-14,18H2,1-4H3,(H2,33,35,40)
comment: Pexmetinib is an orally bioavailable small-molecule inhibitor of p38 MAPK (β isoforms) and Tie2 kinases <Reference id=34908/>. It is a type 2 kinase inhibitor that binds both Tie2 and p38 MAP kinases in the %22DFG-out%22 conformation. p38 MAPK is a proinflammatory kinase, Tie2 is an endothelial cell specific receptor tyrosine kinase and is the receptor for <Ligand id=4867/>. Concomitant inhibition of these kinases is predicted to produce antineoplastic, anti-inflammatory and antiangiogenic effects that would provide a novel anti-cancer therapeutic, in particular for the treatment of myelodysplastic syndromes (MDS) <Reference id=34910/><Reference id=34911/> and acute myeloid leukemia (AML).
iupac name: 1-[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]-3-[[5-fluoro-2-[1-(2-hydroxyethyl)indazol-5-yl]oxyphenyl]methyl]urea
synonym: ARRY-614
synonym: ARRY614
approved: f
ligand name: pexmetinib
type: SyntheticOrganicLigand

panulisib
in ch i key: VJLRLTSXTLICIR-UHFFFAOYSA-N
in ch i: InChI=1S/C27H20F3N9/c1-26(2,13-31)22-7-5-17(11-35-22)39-23-18-8-15(16-9-19(27(28,29)30)24(33)36-10-16)4-6-20(18)34-12-21(23)38(3)25(39)37-14-32/h4-12H,1-3H3,(H2,33,36)
comment: Panulisib (P7170) is a potent small-molecule inhibitor of class I PI3K isoforms, mTOR kinase and activin receptor-like kinase 1 (ALK1) <Reference id=34905/><Reference id=34906/>. It was developed for antiangiogenic efficacy as a novel cancer therapy and has shown efficacy in in vitro and in vivo models of human non-small cell lung cancer <Reference id=34906/>. The chemical structure is claimed in Piramal Life Sciences' patent WO2012007926 where it is example 96 <Reference id=34907/>.
iupac name: [8-[6-amino-5-(trifluoromethyl)pyridin-3-yl]-1-[6-(2-cyanopropan-2-yl)pyridin-3-yl]-3-methylimidazo[4,5-c]quinolin-2-ylidene]cyanamide
synonym: example 96 [WO2012007926A1]
synonym: P7170
approved: f
ligand name: panulisib
type: SyntheticOrganicLigand

pamapimod
in ch i key: JYYLVUFNAHSSFE-UHFFFAOYSA-N
in ch i: InChI=1S/C19H20F2N4O4/c1-25-17-11(10-22-19(24-17)23-13(4-6-26)5-7-27)8-16(18(25)28)29-15-3-2-12(20)9-14(15)21/h2-3,8-10,13,26-27H,4-7H2,1H3,(H,22,23,24)
comment: Pamapimod is an ATP-competitive (Type I), orally bioavailable and highly selective inhibitor of p38α mitogen-activated protein kinase (MAPK14), that was developed for immunomodulatory potential <Reference id=34899/>.
iupac name: 6-(2,4-difluorophenoxy)-2-(1,5-dihydroxypentan-3-ylamino)-8-methylpyrido[2,3-d]pyrimidin-7-one
xref: CHEMBL1090089
synonym: compound 2b [PMID: 21375264]
synonym: Ro4402257
synonym: Ro-4402257
synonym: Ro 4402257
approved: f
ligand name: pamapimod
type: SyntheticOrganicLigand

ilorasertib
in ch i key: WPHKIQPVPYJNAX-UHFFFAOYSA-N
in ch i: InChI=1S/C25H21FN6O2S/c26-17-2-1-3-19(10-17)31-25(34)30-18-6-4-15(5-7-18)21-14-35-23-20(12-28-24(27)22(21)23)16-11-29-32(13-16)8-9-33/h1-7,10-14,33H,8-9H2,(H2,27,28)(H2,30,31,34)
comment: Ilorasertib (ABT-348) is an ATP-competitive, multi-target kinase inhibitor with activity against the Aurora kinases, the VEGFR, PDGFR and Src family kinases <Reference id=34898/>. ABT-348's potent inhibition of Aurora B induces polyploidy, a hallmark of the essential role of Aurora B in cytokinesis.
iupac name: 1-[4-[4-amino-7-[1-(2-hydroxyethyl)pyrazol-4-yl]thieno[3,2-c]pyridin-3-yl]phenyl]-3-(3-fluorophenyl)urea
xref: CHEMBL1980297
synonym: ABT-348
synonym: ABT 348
synonym: ABT348
synonym: A-968660
approved: f
ligand name: ilorasertib
type: SyntheticOrganicLigand

flumbatinib
in ch i key: BJCJYEYYYGBROF-UHFFFAOYSA-N
in ch i: InChI=1S/C29H29F3N8O/c1-19-26(38-28-34-9-7-25(37-28)21-4-3-8-33-16-21)15-23(17-35-19)36-27(41)20-5-6-22(24(14-20)29(30,31)32)18-40-12-10-39(2)11-13-40/h3-9,14-17H,10-13,18H2,1-2H3,(H,36,41)(H,34,37,38)
comment: Flumatinib (HH-GV-678) is a selective, orally bioavailable inhibitor of Bcr-Abl that was developed for antineoplastic potential <Reference id=34896/>. The INN 'flumatinib' was surfaced in WHO Proposed list 125 in July 2021.
iupac name: 4-[(4-methylpiperazin-1-yl)methyl]-N-[6-methyl-5-[(4-pyridin-3-ylpyrimidin-2-yl)amino]pyridin-3-yl]-3-(trifluoromethyl)benzamide
xref: CHEMBL3545413
synonym: HH-GV678
synonym: HHGV-678
synonym: Hansoh Xinfu®
synonym: flumatinib (pseudo INN)
approved: t
ligand name: flumbatinib
type: SyntheticOrganicLigand

α-NETA
canonical SMILES: O=C(c1cccc2c1cccc2)CC[N+](C)(C)C
isomeric SMILES: O=C(c1cccc2c1cccc2)CC[N+](C)(C)C
in ch i key: WZJKPXZLQTXALB-UHFFFAOYSA-N
in ch i: InChI=1S/C16H20NO/c1-17(2,3)12-11-16(18)15-10-6-8-13-7-4-5-9-14(13)15/h4-10H,11-12H2,1-3H3/q+1
comment: α-NETA is a small molecule inhibitor of the chemerin receptor 1 (CMKLR1) <Reference id=34154/>, a chemoattractant receptor involved in leukocyte trafficking. This compound may be used as the iodide salt (PubChem CID 11957648). We show the chemical structure for the parent molecule.
iupac name: trimethyl-(3-naphthalen-1-yl-3-oxopropyl)azanium
xref: CHEMBL1358898
approved: f
ligand name: α-NETA
type: SyntheticOrganicLigand

allitinib
in ch i key: MVZGYPSXNDCANY-UHFFFAOYSA-N
comment: Allitinib (AST-1306) is an irreversible inhibitor of the wild-type epidermal growth factor receptor (EGFR) and ErbB2 (HER2) <Reference id=34894/>. It also inhibits the mutant EGFRT790M/L858R. Allitinib was designed by Allist Pharmaceuticals to overcome acquired resistance to EGFR inhibitor therapy. It is active in vitro and in vivo. Allitinib is a 'pseudo' INN, that takes the form of an INN, but has not been submitted to the World Health Organisation for ratification.
xref: CHEMBL1947204
synonym: ALL-3
synonym: AST-1306
synonym: AST1306
synonym: AST 1306
approved: f
ligand name: allitinib
type: SyntheticOrganicLigand

TAK-733
in ch i key: RCLQNICOARASSR-SECBINFHSA-N
comment: TAK-733 is a potent and selective MEK inhibitor with an allosteric binding mode, that was designed as a novel cancer chemotherapeutic <Reference id=34892/>.
iupac name: 3-[(2R)-2,3-dihydroxypropyl]-6-fluoro-5-(2-fluoro-4-iodoanilino)-8-methylpyrido[2,3-d]pyrimidine-4,7-dione
xref: CHEMBL1615025
synonym: example 18 [US8470837]
synonym: TAK733
synonym: compound 17 [PMID: 21310613]
approved: f
ligand name: TAK-733
type: SyntheticOrganicLigand

CH4987655
in ch i key: FIMYFEGKMOCQKT-UHFFFAOYSA-N
comment: CH4987655 is an orally active allosteric MEK inhibitor that was designed as a novel cancer chemotherapeutic <Reference id=34887/>.
iupac name: 3,4-difluoro-2-[(2-fluoro-4-iodophenyl)amino]-N-(2-hydroxyethoxy)-5-[(3-oxooxazinan-2-yl)methyl]benzamide
xref: CHEMBL1614766
synonym: RO4987655
synonym: compound 24 [PMID: 21316218]
approved: f
ligand name: CH4987655
type: SyntheticOrganicLigand

GDC-0623
canonical SMILES: OCCONC(=O)c1ccc2n(c1Nc1ccc(cc1F)I)cnc2
isomeric SMILES: OCCONC(=O)c1ccc2n(c1Nc1ccc(cc1F)I)cnc2
in ch i key: RFWVETIZUQEJEF-UHFFFAOYSA-N
in ch i: InChI=1S/C16H14FIN4O3/c17-13-7-10(18)1-4-14(13)20-15-12(16(24)21-25-6-5-23)3-2-11-8-19-9-22(11)15/h1-4,7-9,20,23H,5-6H2,(H,21,24)
comment: GDC-0623 (RG-7420) is an ATP-uncompetitive MEK1 inhibitor that was developed by Genentech for anti-cancer potential <Reference id=34885/>. The structure of GDC-0623 was disclosed for the first time in 'Supplementary Figure 1a' provided with Hatzivassiliou et al. (2013) <Reference id=34886/>.
synonym: RG-7421
synonym: RG7421
synonym: RG 7421
synonym: GDC 0623
synonym: GDC0623
synonym: G-868
approved: f
ligand name: GDC-0623
type: SyntheticOrganicLigand

ONO-8590580
in ch i key: INGJMHPGMVUEKY-UHFFFAOYSA-N
in ch i: InChI=1S/C21H21FN6/c1-13-20(22)16(7-18-21(13)25-12-28(18)9-14-3-4-14)26-19-6-5-15(8-23-19)17-10-27(2)11-24-17/h5-8,10-12,14H,3-4,9H2,1-2H3,(H,23,26)
comment: A novel GABAA α5 negative allosteric modulator that enhances hippocampal memory function without an anxiogenic or proconvulsant risk.
iupac name: 1-(cyclopropylmethyl)-5-fluoro-4-methyl-N-[5-(1-methyl-1H-imidazol-4-yl)pyridin-2-yl]-1H-1,3-benzodiazol-6-amine
approved: f
ligand name: ONO-8590580
type: SyntheticOrganicLigand

tenalisib
in ch i key: HDXDQPRPFRKGKZ-INIZCTEOSA-N
in ch i: InChI=1S/C23H18FN5O2/c1-2-16(29-23-19-22(26-11-25-19)27-12-28-23)21-18(13-6-5-7-14(24)10-13)20(30)15-8-3-4-9-17(15)31-21/h3-12,16H,2H2,1H3,(H2,25,26,27,28,29)/t16-/m0/s1
comment: Tenalisib (RP6530) is an orally active dual PI3K δ/γ inhibitor that is being developed by Rhizen Pharmaceuticals for the potential oral treatment of cancer <Reference id=40827/> and inflammation. The chemical structure and its use are claimed in patent US9790224 where it is called Compound A1 <Reference id=34882/>.
iupac name: 3-(3-fluorophenyl)-2-[(1S)-1-[(9H-purin-6-yl)amino]propyl]-4H-chromen-4-one
synonym: RP6530
synonym: RP-6530
synonym: RP 6530
approved: f
ligand name: tenalisib
type: SyntheticOrganicLigand

teneligliptin
in ch i key: WGRQANOPCQRCME-PMACEKPBSA-N
in ch i: InChI=1S/C22H30N6OS/c1-17-13-21(28(24-17)18-5-3-2-4-6-18)26-9-7-25(8-10-26)19-14-20(23-15-19)22(29)27-11-12-30-16-27/h2-6,13,19-20,23H,7-12,14-16H2,1H3/t19-,20-/m0/s1
comment: Teneligliptin is a long-acting, orally bioavailable dipeptidyl peptidase 4 (DPP-4) inhibitor <Reference id=34851/>. It was developed for clinical potential in type 2 diabetes management, to improve glycemic control. In addition to their anti-diabetic activity, DPP4 inhibitors may have renal and cardiovascular protective effects.
iupac name: [(2S,4S)-4-[4-(5-methyl-2-phenylpyrazol-3-yl)piperazin-1-yl]pyrrolidin-2-yl]-(1,3-thiazolidin-3-yl)methanone
xref: CHEMBL2147777
synonym: MP-513
synonym: MP513
synonym: compound 8g [PMID: 22959556]
synonym: Teneli
approved: t
ligand name: teneligliptin
type: SyntheticOrganicLigand

compound 8i [PMID: 22765894]
isomeric SMILES: CCN1CCC(CC1)Nc1ccc2c(c1)/C(=C(/c1ncc([nH]1)C)/c1cccc(c1)F)/C(=O)N2
in ch i key: DMQYDVBIPXAAJA-VHXPQNKSSA-N
in ch i: InChI=1S/C26H28FN5O/c1-3-32-11-9-19(10-12-32)30-20-7-8-22-21(14-20)24(26(33)31-22)23(25-28-15-16(2)29-25)17-5-4-6-18(27)13-17/h4-8,13-15,19,30H,3,9-12H2,1-2H3,(H,28,29)(H,31,33)/b24-23-
comment: Compound 8i is a multi-target receptor tyrosine kinase inhibitor <Reference id=26973/>. The chemical structure matches that ascribed to the Exelixis compound XL999 presented by MedKoo, but there is no peer reviewed confirmation of this nomenclature linkage. Compound 8i does not alter c-MET activity, so its effects can be compared to those of <Ligand id=5679/> and/or <Ligand id=5887/> which are c-MET inhibitors, to help assess the contribition that inhibition of the different kinases makes to measured outcomes (e.g. antiproliferative effect).
iupac name: (3Z)-5-[(1-ethylpiperidin-4-yl)amino]-3-[(3-fluorophenyl)-(5-methyl-1H-imidazol-2-yl)methylidene]-1H-indol-2-one
xref: CHEMBL2087167
approved: f
ligand name: compound 8i [PMID: 22765894]
type: SyntheticOrganicLigand

EG01377
in ch i key: SEXUXSMBJLNXIR-FQEVSTJZSA-N
in ch i: InChI=1S/C26H30N6O6S2/c27-14-15-3-5-16(6-4-15)18-12-17-7-10-38-22(17)21(13-18)40(36,37)32-19-8-11-39-23(19)24(33)31-20(25(34)35)2-1-9-30-26(28)29/h3-6,8,11-13,20,32H,1-2,7,9-10,14,27H2,(H,31,33)(H,34,35)(H4,28,29,30)/t20-/m0/s1
comment: EG01377 is a neuropilin 1 (NRP1) antagonist <Reference id=34812/>.
iupac name: (2S)-2-[(3-{5-[4-(aminomethyl)phenyl]-2,3-dihydro-1-benzofuran-7-sulfonamido}thiophen-2-yl)formamido]-5-carbamimidamidopentanoic acid
synonym: (3-((5-(4-(aminomethyl)phenyl)-2,3-dihydrobenzofuran)-7-sulfonamido)thiophene- 2-carbonyl)-L-arginine
synonym: compound 1 [PMID: 29648813]
approved: f
ligand name: EG01377
type: SyntheticOrganicLigand

samuraciclib
in ch i key: YCVGLKWJKIKVBI-MJGOQNOKSA-N
in ch i: InChI=1S/C22H30N6O/c1-15(2)18-13-26-28-21(25-11-16-6-4-3-5-7-16)10-20(27-22(18)28)24-12-17-8-9-23-14-19(17)29/h3-7,10,13,15,17,19,23,25,29H,8-9,11-12,14H2,1-2H3,(H,24,27)/t17-,19+/m1/s1
comment: Samuraciclib (ICEC0942, a.k.a. CT7001) is an orally available, non-covalent, selective inhibitor of cyclin dependent kinase 7 (CDK7) that was developed as a new transcription-targeting approach for potential cancer therapy <Reference id=34833/>. It was developed by the same group who identified <Ligand id=9405/>. The chemical structure is claimed in patent US20160362410A1 <Reference id=34834/>.
iupac name: (3R,4R)-4-[[[7-(benzylamino)-3-propan-2-ylpyrazolo[1,5-a]pyrimidin-5-yl]amino]methyl]piperidin-3-ol
synonym: PPDA-001
synonym: CT7001
synonym: ICEC0942
synonym: ICEC-0942
approved: f
ligand name: samuraciclib
type: SyntheticOrganicLigand

uracil 20
in ch i key: BTGMTHBOODBMHN-SUHMBNCMSA-N
in ch i: InChI=1S/C33H33N5O7/c1-18(2)37-17-26(29(41)38(32(37)44)33(12-13-33)31(43)36-25-16-27(39)45-30(25)42)35-28(40)24-11-10-22(14-19(24)3)34-23-9-8-20-6-4-5-7-21(20)15-23/h4-11,14-15,17-18,25,30,34,42H,12-13,16H2,1-3H3,(H,35,40)(H,36,43)/t25-,30?/m0/s1
comment: Uracil 20 is a small molecule caspase-1 inhibitor that was developed as a topically active anti-inflammatory agent for the treatment of inflammatory acne <Reference id=34805/>. This compound contrasts with the caspase -1 inhibitors <Ligand id=9035/> and <Ligand id=6467/> which were designed for systemic exposure.
iupac name: N-(3-(1-(((3S)-2-Hydroxy-5-oxotetrahydrofuran-3-yl)carbamoyl)cyclopropyl)-1- isopropyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)-2-methyl-4-(naphthalen-2- ylamino)benzamide
approved: f
ligand name: uracil 20
type: SyntheticOrganicLigand

praliciguat
in ch i key: CYSJNTQNMDWAJV-UHFFFAOYSA-N
in ch i: InChI=1S/C21H14F8N6O2/c22-12-4-2-1-3-11(12)9-35-16(14-5-6-37-34-14)7-15(33-35)18-30-8-13(23)17(32-18)31-10-19(36,20(24,25)26)21(27,28)29/h1-8,36H,9-10H2,(H,30,31,32)
comment: Praliciguat (IW-1973) is a potent, orally available soluble guanylyl cyclase (sGC) stimulator <Reference id=34835/>. sGC stimulators/activators have potential as heart failure therapeutics <Reference id=34982/>. Praliciguat exhibits anti-hypertensive, reno-protective, anti-fibrotic effects and anti-inflammatory activities. Effects observed in renal fibrosis models suggests potential for the treatment of diabetic nephropathy.
iupac name: 1,1,1-trifluoro-3-[(5-fluoro-2-{1-[(2-fluorophenyl)methyl]-5-(1,2-oxazol-3-yl)-1H-pyrazol-3-yl}pyrimidin-4-yl)amino]-2-(trifluoromethyl)propan-2-ol
synonym: IW-1973
synonym: IW1973
approved: f
ligand name: praliciguat
type: SyntheticOrganicLigand

AH10-7
in ch i key: AACQUTZHAXVZEB-MMSUBXCOSA-N
comment: AH10-7 is a sphinganine α-galactosylceramide (or galactosylsphingamide) that has been designed for the potential to activate CD1d-restricted invariant natural killer T (iNKT) cells as a mechanism to augment immune responses against cancer and infections <Reference id=34758/>. It is an analogue of KRN7000 (PubChem CID 2826713, a.k.a. α-GalCer) that was originally developed for its potent immunomodulatory effects, and which was investigated as an immuno-oncology agent <Reference id=34760/><Reference id=34761/>. However, KRN7000 induces both Th1 and Th2 cytokine production, and produces a suboptimal immune response, which likely accounts for its apparent limited efficacy in clinical trials <Reference id=34762/><Reference id=34763/>. AH10-7 overcomes KRN7000's unpredictable effects by promoting a Th1-biased immune response, which suggests that it will elicit more favorable results against cancer and infection (whereas a Th2-biased response would likely be of more benefit against autoimmune diseases). Both KRN7000 and AH10-7 are ligands for the lipid-binding MHC class I-like protein CD1d. Recognition of lipid-based antigens presented by CD1d sets iNKT cells apart from conventional T cells. Van Kaer and Wu (2018) have published a review of the therapeutic potential of iNKT cells in autoimmune conditions <Reference id=34759/> and the application of unconventional T cells in immuno-oncology is reviewed by Godfrey et al. (2018) <Reference id=34764/> and Krijgsman et al. (2018) <Reference id=34765/>.
iupac name: N-[(2S,3R)-3-hydroxy-1-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-{[(4-phenylbut-1-en-2-yl)oxy]methyl}oxan-2-yl]oxy}octadecan-2-yl]hexacosanamide
approved: f
ligand name: AH10-7
type: SyntheticOrganicLigand

SAR-20347
in ch i key: HEDPDFHTQKEORT-UHFFFAOYSA-N
comment: SAR-20347 is an experimental small molecule Janus kinase 1 (JAK1)/ tyrosine kinase 2 (TYK2) inhibitor <Reference id=34223/>. It has anti-inflammatory potential, via inhibition of Th17 proinflammatory cytokine production (e.g. IL-22 and IL-23) and signaling.
approved: f
ligand name: SAR-20347
type: SyntheticOrganicLigand

inhibitor 32 [PMID: 29620892]
in ch i key: ZYFVLHYHXNFROE-KRWDZBQOSA-N
in ch i: InChI=1S/C21H33N3O4/c1-2-3-10-17(13-9-16-21(27)24-28)22-19(25)14-7-8-15-20(26)23-18-11-5-4-6-12-18/h4-6,11-12,17,28H,2-3,7-10,13-16H2,1H3,(H,22,25)(H,23,26)(H,24,27)/t17-/m0/s1
comment: Inhibitor 32 is a novel autotaxin inhibitor whose structure is based on the non-natural δ-norleucine scaffold <Reference id=34756/>.
approved: f
ligand name: inhibitor 32 [PMID: 29620892]
type: SyntheticOrganicLigand

MPPA
in ch i key: IJNCJYJSEFDKFC-UHFFFAOYSA-N
in ch i: InChI=1S/C18H23F3N2O3/c1-3-16(24)23-8-6-12(7-9-23)17(25)22-11-13-4-5-14(26-2)10-15(13)18(19,20)21/h4-5,10,12H,3,6-9,11H2,1-2H3,(H,22,25)
comment: MMPA is an orally bioavailable dual inhibitor of soluble epoxide hydrolase (sEH) and phosphodiesterase 4 (PDE4) <Reference id=34755/>. It was designed to provide enhanced analgesia for the treatment of inflammatory pain. MMPA can be described as a polypharmacological agent, i.e. a single molecule with at least two pharmacophores in a novel molecular design.
iupac name: N-{[4-methoxy-2-(trifluoromethyl)phenyl]methyl}-1-propanoylpiperidine-4-carboxamide
synonym: inhibitor 23 [PMID: 29614224]
approved: f
ligand name: MPPA
type: SyntheticOrganicLigand

compound 1 [Vakkeel et al., 2018]
in ch i key: CCIKYPZLPYEMFX-UHFFFAOYSA-N
in ch i: InChI=1S/C37H46N10O10/c1-20-13-26(56-12-8-11-43-46-40)14-21(2)33(20)35(50)45-28(18-41-32(48)19-42-34(49)24-9-7-10-25(15-24)44-37(38)39)36(51)57-23(4)22(3)27-16-30(54-5)31(55-6)17-29(27)47(52)53/h7,9-10,13-17,22-23,28H,8,11-12,18-19H2,1-6H3,(H,41,48)(H,42,49)(H,45,50)(H4,38,39,44)
comment: Compound 1 is a photoactivatable α5β1 integrin ligand <Reference id=34743/>. Structurally it is a selective α5β1 integrin ligand (a peptidomimetic of the RGD adhesive motif found in several extracellular matrix (ECM) proteins) linked to a 3-(4,5-Dimethoxy-2-nitrophenyl)-2-butyl ester (DMNPB) photocleavable chromophore. When intact, the compound is unable to bind the integrin, but upon exposure to light the chromophore is cleaved and the ligand then behaves as an antagonist of α5β1 interaction with ECM substrates. The photactivation of compound 1 allows precise, in situ, dose-responsive and temporal study of the role played by α5β1 integrin-dependent processes in cell adhesion and migration. α5β1 integrin is a molecular target that plays recognised roles in tumour angiogenesis and cancer cell migration and metastasis <Reference id=34744/><Reference id=34747/>, that is being expoilted for clinical utility in cancer indications <Reference id=34750/><Reference id=34748/><Reference id=34745/>. α5β1 may also be an immune system/inflammation relevant target <Reference id=34746/><Reference id=34749/>.
approved: f
ligand name: compound 1 [Vakkeel et al., 2018]
type: SyntheticOrganicLigand

esaxerenone
in ch i key: NOSNHVJANRODGR-UHFFFAOYSA-N
comment: Selective antagonist of the mineralocorticoid receptor that has progressed to clinical trials in a number of indications <Reference id=35004/>.
iupac name: 1-(2-hydroxyethyl)-4-methyl-N-(4-methylsulfonylphenyl)-5-[2-(trifluoromethyl)phenyl]pyrrole-3-carboxamide
xref: CHEMBL2181932
synonym: CS-3150
synonym: XL-550
approved: t
ligand name: esaxerenone
type: SyntheticOrganicLigand

compound 9 [PMID: 20718420]
canonical SMILES: OB(C1CCCN1C(=O)CNC(=O)c1cccc2c1cccc2)O
in ch i key: QVGIJGPVKMNEPA-HNNXBMFYSA-N
in ch i: InChI=1S/C17H19BN2O4/c21-16(20-10-4-9-15(20)18(23)24)11-19-17(22)14-8-3-6-12-5-1-2-7-13(12)14/h1-3,5-8,15,23-24H,4,9-11H2,(H,19,22)/t15-/m0/s1
comment: Compound 9 is a selective inhibitor of the prolyl serine peptidase fibroblast activation protein (FAP) <Reference id=34739/>. FAP inhibitors were developed as potential anti-tumour agents, but failed to show significant clinical efficacy in cancer patients.
iupac name: [(2R)-1-[2-(naphthalene-1-carbonylamino)acetyl]pyrrolidin-2-yl]boronic acid
xref: CHEMBL1243373
approved: f
ligand name: compound 9 [PMID: 20718420]
type: SyntheticOrganicLigand

talabostat
canonical SMILES: CC(C(C(=O)N1CCCC1B(O)O)N)C
isomeric SMILES: CC([C@@H](C(=O)N1CCC[C@H]1B(O)O)N)C
in ch i key: FKCMADOPPWWGNZ-YUMQZZPRSA-N
in ch i: InChI=1S/C9H19BN2O3/c1-6(2)8(11)9(13)12-5-3-4-7(12)10(14)15/h6-8,14-15H,3-5,11H2,1-2H3/t7-,8-/m0/s1
comment: Talabostat (PT-100, or Val-boroPro) is a compound with potent anti-tumour activity. It is a non-selective inhibitor of post-proline-cleaving serine proteases. Talabostat activates macrophages at least in part via inhibition of the serine peptidase, fibroblast activation protein (FAP) , an action that has been examined for anti-cancer utility <Reference id=34732/><Reference id=34733/><Reference id=34734/> and anti-fibrotic potential <Reference id=34731/>. More recently talabostat has been reported as an inhibitor of the cytosolic serine dipeptidyl peptidases Dpp8 and Dpp9, and that inhibition of these related enzymes stimulates the immune system via the selective promotion of proinflammatory cell death (pyroptosis) of monocytes and macrophages <Reference id=34736/>. This process involves Dpp8/9-induced activation of the NOD-like pattern recognition receptor NLRP1, a protein that acts as an inflammasome sensor, followed by activation of pro-caspase-1 and eventually to pyroptosis <Reference id=34735/>.
iupac name: [(2R)-1-[(2S)-2-amino-3-methylbutanoyl]pyrrolidin-2-yl]boronic acid
xref: CHEMBL67279
synonym: PT-100
synonym: PT100
synonym: Val-boro-pro
synonym: Val-boroPro
synonym: compound 1 [PMID: 18783201]
approved: f
ligand name: talabostat
type: SyntheticOrganicLigand

marbostat-100
in ch i key: ZCAIUGLOTHAUQX-UHFFFAOYSA-N
in ch i: InChI=1S/C22H20N4O4/c1-24-21(28)16-11-25(22(24)29)12-18-19(16)15-4-2-3-5-17(15)26(18)10-13-6-8-14(9-7-13)20(27)23-30/h2-9,16,30H,10-12H2,1H3,(H,23,27)
comment: Marbostat-100 is a histone deacetylase (HDAC) inhibitor that is selective for HDAC6 <Reference id=34727/>. It is a lead structure identified by structure-activity-relationship and medicinal chemistry efforts. HDAC6 isoform-specific compounds are predicted to provide anti-inflammatory activity relevant to the treatment of chronic immune and inflammatory disorders.
synonym: compound 5a [PMID: 29589441]
approved: f
ligand name: marbostat-100
type: SyntheticOrganicLigand

MIDD0301
in ch i key: OSBXEAZWQGBYFU-SNVBAGLBSA-N
comment: MIDD0301 is a positive allosteric GABAAR modulator <Reference id=34723/>. MIDD0301 targets specific GABA receptor subtypes (α4- and α5-containing receptors) that are selectively expressed in airway smooth muscle, airway epithelium, and inflammatory cells <Reference id=34726/><Reference id=34725/>, and in this way offers the potential to alleviate asthma pathophysiology with a reduced likelihood of causing systemic side effects. It acts both as a bronchodilator and as an anti-inflammatory agent.
approved: f
ligand name: MIDD0301
type: SyntheticOrganicLigand

RP-101075
in ch i key: WGUXQKIWMYYPQI-SFHVURJKSA-N
in ch i: InChI=1S/C21H20N4O2/c1-12(2)26-19-9-6-13(10-14(19)11-22)21-24-20(25-27-21)17-5-3-4-16-15(17)7-8-18(16)23/h3-6,9-10,12,18H,7-8,23H2,1-2H3/t18-/m0/s1
comment: RP-101075 is an active metabolite of <Ligand id=8709/> <Reference id=34722/>. It demonstrates similar in vitro specificity for S1P receptors as ozanimod and has a comparable pharmacodynamic profile in vivo.
approved: f
ligand name: RP-101075
type: SyntheticOrganicLigand

MDG 548
in ch i key: WJNBKDZARWFFKR-UHFFFAOYSA-N
comment: MDG 548 is a peroxisome proliferator-activated receptor γ (PPARγ) agonist that was identified by virtual screening, and validated by in vitro assays <Reference id=34718/>.
iupac name: 5-[(3-chloro-4-phenylmethoxyphenyl)methylidene]-2-sulfanylidene-1,3-diazinane-4,6-dione
xref: CHEMBL2064741
synonym: MDG548
synonym: MDG-548
synonym: compound 1 [PMID: 22582973]
approved: f
ligand name: MDG 548
type: SyntheticOrganicLigand

L-cysteate
canonical SMILES: [O-]C(=O)C(CS(=O)(=O)O)N
isomeric SMILES: [O-]C(=O)C(CS(=O)(=O)O)N
in ch i key: XVOYSCVBGLVSOL-UHFFFAOYSA-M
in ch i: InChI=1S/C3H7NO5S/c4-2(3(5)6)1-10(7,8)9/h2H,1,4H2,(H,5,6)(H,7,8,9)/p-1
iupac name: 2-amino-3-sulfopropanoate
synonym: cysteate
approved: f
ligand name: L-cysteate
type: MetaboliteLigand

JH-XI-10-02
in ch i key: JECHBTRAPARMGI-KMIZWFMDSA-N
in ch i: InChI=1S/C53H69N5O9/c1-52-19-15-38(32-37(52)9-10-39-42-12-11-41(53(42,2)20-16-43(39)52)35-8-7-34-17-21-54-33-36(34)31-35)57(3)47(60)18-23-64-25-27-66-29-30-67-28-26-65-24-22-55-44-6-4-5-40-48(44)51(63)58(50(40)62)45-13-14-46(59)56-49(45)61/h4-8,17,21,31,33,37-39,41-43,45,55H,9-16,18-20,22-30,32H2,1-3H3,(H,56,59,61)/t37?,38-,39-,41+,42-,43?,45?,52-,53+/m0/s1
comment: JH-XI-10-02 is a bivalent molecule described as a PROTAC (proteolysis targeting chimera) that simultaneously inhibits CDK8 kinase activity and recruits E3 ligase CRL4Cereblon to target CDK8 for destruction via E3 ligase-mediated ubiquitination and proteasomal degradation. JH-XI-10-02 contains a <Ligand id=7348/> domain that is connected to the CDK8 inhibitor via a PEG linker. It is the pomalidomide moiety that binds to the ubiquitously expressed E3 ligase receptor cereblon. The kinase inhibitor portion of the molecule is almost identical to <Ligand id=9886/>.
approved: f
ligand name: JH-XI-10-02
type: SyntheticOrganicLigand

JH-VIII-49
in ch i key: IWZSHWBGHQBIML-ZGGLMWTQSA-N
in ch i: InChI=1S/C30H40N2/c1-29-14-11-24(32(3)4)18-23(29)7-8-25-27-10-9-26(30(27,2)15-12-28(25)29)21-6-5-20-13-16-31-19-22(20)17-21/h5-7,13,16-17,19,24-28H,8-12,14-15,18H2,1-4H3/t24-,25-,26+,27-,28?,29-,30+/m0/s1
comment: JH-VIII-49 is a synthetically produced analogue of the natural product <Ligand id=9885/> <Reference id=34710/>. Like cortistatin A, JH-VIII-49 is a potent inhibitor of CDK8. Inhibition of CDK8 by small molecular agents is being explored as a novel mechanism for cancer therapy.
synonym: compound 19 [Hatcher et al., 2018]
approved: f
ligand name: JH-VIII-49
type: SyntheticOrganicLigand

cortistatin A
in ch i key: KSGZCKSNTAJOJS-DZBMUNJRSA-N
in ch i: InChI=1S/C30H36N2O3/c1-28-10-8-21-15-23-26(33)27(34)24(32(2)3)16-29(23)11-12-30(21,35-29)25(28)7-6-22(28)19-5-4-18-9-13-31-17-20(18)14-19/h4-5,8-9,13-15,17,22,24-27,33-34H,6-7,10-12,16H2,1-3H3/t22-,24+,25-,26-,27-,28-,29-,30-/m1/s1
comment: Cortistatin A is a steroidal alkaloid isolated from the marine sponge Corticium simplex. It is a high affinity inhibitor of several protein kinases, including ROCK, CDK8, and CDK11 <Reference id=34704/>. It has anti-proliferative and anti-angoiogenic activities <Reference id=34705/><Reference id=34704/>.
synonym: (+)-cortistatin A
synonym: 17-epi-cortistatin A
approved: f
ligand name: cortistatin A
type: NaturalProductLigand

BMS-962212
in ch i key: WYFCZWSWFGJODV-MIANJLSGSA-N
comment: BMS-962212 is a reversible, direct, and highly selective small molecule inhibitor of the serine protease FXIa <Reference id=34702/>.
iupac name: 4-[[(1S)-2-[(E)-3-[3-chloro-2-fluoro-6-(tetrazol-1-yl)phenyl]prop-2-enoyl]-5-(4-methyl-2-oxopiperazin-1-yl)-3,4-dihydro-1H-isoquinoline-1-carbonyl]amino]benzoic acid
synonym: compound 55 [PMID: 29077405]
synonym: BMS962212
synonym: BMS 962212
approved: f
ligand name: BMS-962212
type: SyntheticOrganicLigand

compound 46c [PMID: 29350534]
in ch i key: QPAGOTNPJABYCP-FITNPZAZSA-N
in ch i: InChI=1S/C28H38N4O/c1-2-8-24-20-31-26(19-23(24)7-1)21-32(16-4-3-14-29-25-12-17-33-18-13-25)27-11-5-9-22-10-6-15-30-28(22)27/h1-4,6-8,10,15,25-27,29,31H,5,9,11-14,16-21H2/b4-3+/t26-,27+/m1/s1
comment: Compound 46c is a CXCR4 antagonist. It is a structural analogue of <Ligand id=9882/> <Reference id=34698/>. CXCR4 antagonists are being developed for potential clinical utility as anti-cancer agents. Compared to TIQ-15, 46c has improved predicted intestinal permeability and reduced inhibition of CYP450 2D6, which is one of the most important hepatic drug-metabolising enzymes, and inhibition of which can cause adverse drug-drug interactions. These enhanced drug-like features make 46c a more suitable clinical lead than TIQ-15.
approved: f
ligand name: compound 46c [PMID: 29350534]
type: SyntheticOrganicLigand

TIQ-15
canonical SMILES: NCCCCN(C1CCCc2c1nccc2)CC1NCc2c(C1)cccc2
in ch i key: MYCKNKHATQGHEV-YADHBBJMSA-N
in ch i: InChI=1S/C23H32N4/c24-12-3-4-14-27(22-11-5-9-18-10-6-13-25-23(18)22)17-21-15-19-7-1-2-8-20(19)16-26-21/h1-2,6-8,10,13,21-22,26H,3-5,9,11-12,14-17,24H2/t21-,22+/m1/s1
comment: TIQ-15 is a CXCR4 antagonist <Reference id=34698/>. It is the parent molecule of the analogue <Ligand id=9883/>. CXCR4 antagonists are being developed for potential clinical utility as anti-cancer agents. However, TIQ-15 is unsatisfactory as a clinical lead as it suffers from poor oral bioavailability and off-target liabilities (primarily inhibition of the central hepatic drug-metabolising enzyme CYP450 2D6).
iupac name: N'-[[(3R)-1,2,3,4-tetrahydroisoquinolin-3-yl]methyl]-N'-[(8S)-5,6,7,8-tetrahydroquinolin-8-yl]butane-1,4-diamine
xref: CHEMBL3091687
approved: f
ligand name: TIQ-15
type: SyntheticOrganicLigand

EBI-2511
in ch i key: NYWVSLBALKNFJR-UHFFFAOYSA-N
in ch i: InChI=1S/C34H48N4O4/c1-7-26-29(38(8-2)25-11-15-41-16-12-25)19-31-27(18-30(42-31)24-9-13-37(14-10-24)21(3)4)32(26)34(40)35-20-28-22(5)17-23(6)36-33(28)39/h17-19,21,24-25H,7-16,20H2,1-6H3,(H,35,40)(H,36,39)
comment: EBI-2511 is a potent and orally active EZH2 inhibitor that was designed for clinical anti-neoplastic potential <Reference id=34694/>.
iupac name: N-[(4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl]-5-ethyl-6-[ethyl(oxan-4-yl)amino]-2-[1-(propan-2-yl)piperidin-4-yl]-1-benzofuran-4-carboxamide
synonym: compound 34 [PMID: 29456795]
synonym: EBI2511
synonym: EBI 2511
approved: f
ligand name: EBI-2511
type: SyntheticOrganicLigand

H05
canonical SMILES: CN(CCC(c1ccc(cc1)F)Oc1cccc2c1OCO2)C
isomeric SMILES: CN(CCC(c1ccc(cc1)F)Oc1cccc2c1OCO2)C
in ch i key: XFCIOLPMKMDDNQ-UHFFFAOYSA-N
in ch i: InChI=1S/C18H20FNO3/c1-20(2)11-10-15(13-6-8-14(19)9-7-13)23-17-5-3-4-16-18(17)22-12-21-16/h3-9,15H,10-12H2,1-2H3
comment: A novel serotonin and norepinephrine reuptake inhibitor with 5-HT2A antagonist activity.
iupac name: (3-(benzo[d] [1,3] dioxol-4-yloxy)-3-(4-fluorophenyl)-N, N-dimethylpropan-1-amine
approved: f
ligand name: H05
type: SyntheticOrganicLigand

tetomilast
in ch i key: XDBHURGONHZNJF-UHFFFAOYSA-N
in ch i: InChI=1S/C19H18N2O4S/c1-3-24-16-9-8-12(10-17(16)25-4-2)18-21-15(11-26-18)13-6-5-7-14(20-13)19(22)23/h5-11H,3-4H2,1-2H3,(H,22,23)
comment: Tetomilast is a PDE4 inhibitor. Inhibition of PDE4 blocks the oxidative burst in human neutrophils, which is a major mediator of tissue injury in inflammatory diseases. Tetomilast (OPC-6535) was originally identified as an inhibitor of superoxide production by human neutrophils <Reference id=34662/>. The clinical potential of PDE4 inhibition in inflammatory bowel disease was reviewed by Salari and Abdollahiin 2012 <Reference id=34663/>.
iupac name: 6-[2-(3,4-diethoxyphenyl)-1,3-thiazol-4-yl]pyridine-2-carboxylic acid
xref: CHEMBL332750
synonym: OPC-6535
synonym: OPC6535
synonym: OPC 6535
synonym: compound 19f [PMID: 7830278]
approved: f
ligand name: tetomilast
type: SyntheticOrganicLigand

pelubiprofen
canonical SMILES: OC(=O)C(c1ccc(cc1)C=C1CCCCC1=O)C
isomeric SMILES: OC(=O)C(c1ccc(cc1)/C=C/1/CCCCC1=O)C
in ch i key: AUZUGWXLBGZUPP-GXDHUFHOSA-N
in ch i: InChI=1S/C16H18O3/c1-11(16(18)19)13-8-6-12(7-9-13)10-14-4-2-3-5-15(14)17/h6-11H,2-5H2,1H3,(H,18,19)/b14-10+
comment: Pelubiprofen is a nonsteroidal anti-inflammatory type compound <Reference id=34645/>. Structurally it is an aryl propionic acid derivative, like <Ligand id=2713/>. The INN-defined agent is a racemic mixture of enantiomers. We show the structure without specified stereochemistry to represent the mixture. Pelubiprofen is described as a prodrug of 2-arylpropionic acid with modest selectivity for COX2 <Reference id=34643/>.
iupac name: 2-[4-[(E)-(2-oxocyclohexylidene)methyl]phenyl]propanoic acid
xref: CHEMBL69308
synonym: DW-330SR
synonym: DW330SR
synonym: RS-2131
synonym: compound 13b [PMID: 6607354]
synonym: CS-670
approved: f
ligand name: pelubiprofen
type: SyntheticOrganicLigand

ONO-9054
in ch i key: BKVUSNOUTQMSBE-XCMGCKIWSA-N
in ch i: InChI=1S/C26H36F2O6/c1-16(2)34-26(31)5-3-4-17-6-9-21-20(23(30)13-24(21)32-14-17)10-8-19(29)15-33-25-12-18(27)7-11-22(25)28/h7-8,10-12,16-17,19-21,23-24,29-30H,3-6,9,13-15H2,1-2H3/b10-8+/t17-,19+,20+,21+,23+,24-/m0/s1
comment: Agonist at both the prostanoid FP and EP3 receptors that has clinical efficacy as an ocular hypotensive agent <Reference id=34774/><Reference id=34775/><Reference id=34854/>.
iupac name: propan-2-yl 4-[(3S,5aR,6R,7R,8aS)-6-[(E,3R)-4-(2,5-difluorophenoxy)-3-hydroxybut-1-enyl]-7-hydroxy-3,4,5,5a,6,7,8,8a-octahydro-2H-cyclopenta[b]oxepin-3-yl]butanoate
synonym: sepetaprost
approved: f
ligand name: ONO-9054
type: SyntheticOrganicLigand

VUF14862
isomeric SMILES: O=C(c1cccc(c1)/N=N/c1cccc(c1)OC1C[C@H](C1)N1CCCCC1)N1CCCC1
in ch i key: QQXICCNAEXQIHK-JMBHWGOTSA-N
in ch i: InChI=1S/C26H32N4O2/c31-26(30-14-4-5-15-30)20-8-6-9-21(16-20)27-28-22-10-7-11-24(17-22)32-25-18-23(19-25)29-12-2-1-3-13-29/h6-11,16-17,23,25H,1-5,12-15,18-19H2/b28-27+/t23-,25?
comment: VUF14862 is a bidirectional photo-switchable histamine H3 receptor antagonist based on the structure of <Ligand id=9872/> <Reference id=34638/>. The chemical structure shown here is the photo-activated isomer that binds the H3 receptor under UV illumination. VUF14862 binding is 'switched-off' by UV light. VUF14862 swiftly and reversibly photoisomerizes (via trans/cis conversion) and is suitable for spatiotemporal studies of H3 receptor signaling. See also <Ligand id=9873/>, which operates in the opposite direction.
iupac name: 1-(3-{3-[(E)-2-[3-(pyrrolidine-1-carbonyl)phenyl]diazen-1-yl]phenoxy}cyclobutyl)piperidine
synonym: VUF-14862
synonym: VUF 14862
synonym: compound 33 [PMID: 29470065]
approved: f
ligand name: VUF14862
type: SyntheticOrganicLigand

VUF14738
isomeric SMILES: O=C(c1cccc(c1)/N=N/c1cccc(c1)OCCCN1CCCCC1)N1CCCC1
in ch i key: AXFRZIJLVKELGM-RQZHXJHFSA-N
in ch i: InChI=1S/C25H32N4O2/c30-25(29-16-4-5-17-29)21-9-6-10-22(19-21)26-27-23-11-7-12-24(20-23)31-18-8-15-28-13-2-1-3-14-28/h6-7,9-12,19-20H,1-5,8,13-18H2/b27-26-
comment: VUF14738 is a bidirectional photo-switchable histamine H3 receptor antagonist based on the structure of <Ligand id=9872/> <Reference id=34638/>. The chemical structure shown here is the photo-activated isomer that binds the H3 receptor under UV illumination. VUF14738 binding is 'switched-on' by UV light. VUF14738 swiftly and reversibly photoisomerizes (via trans/cis conversion) and is suitable for spatiotemporal studies of H3 receptor signaling. See also <Ligand id=9874/>, which operates in the opposite direction.
iupac name: 1-(3-{3-[(Z)-2-[3-(pyrrolidine-1-carbonyl)phenyl]diazen-1-yl]phenoxy}propyl)piperidine
synonym: VUF 14738
synonym: VUF-14738
synonym: compound 28 [PMID: 29470065]
approved: f
ligand name: VUF14738
type: SyntheticOrganicLigand

compound 3a [PMID: 18606542]
in ch i key: KBLLVDUPDMDMON-UHFFFAOYSA-N
in ch i: InChI=1S/C23H30N2O2/c26-23(25-14-4-5-15-25)21-8-7-20-18-22(10-9-19(20)17-21)27-16-6-13-24-11-2-1-3-12-24/h7-10,17-18H,1-6,11-16H2
comment: Compound 3a is an inverse agonist (as determined by functional GTPγS assay) of the histamine H3 receptor <Reference id=34639/>.
xref: CHEMBL476099
approved: f
ligand name: compound 3a [PMID: 18606542]
type: SyntheticOrganicLigand

pixatimod
in ch i key: LNUFLCYMSVYYNW-ZPJMAFJPSA-N
in ch i: InChI=1S/C51H88O60S13/c1-22(2)7-6-8-23(3)27-11-12-28-26-10-9-24-17-25(13-15-50(24,4)29(26)14-16-51(27,28)5)95-46-42(108-121(79,80)81)38(104-117(67,68)69)34(30(96-46)18-91-112(52,53)54)100-47-43(109-122(82,83)84)39(105-118(70,71)72)35(31(97-47)19-92-113(55,56)57)101-48-44(110-123(85,86)87)40(106-119(73,74)75)36(32(98-48)20-93-114(58,59)60)102-49-45(111-124(88,89)90)41(107-120(76,77)78)37(103-116(64,65)66)33(99-49)21-94-115(61,62)63/h22-49H,6-21H2,1-5H3,(H,52,53,54)(H,55,56,57)(H,58,59,60)(H,61,62,63)(H,64,65,66)(H,67,68,69)(H,70,71,72)(H,73,74,75)(H,76,77,78)(H,79,80,81)(H,82,83,84)(H,85,86,87)(H,88,89,90)/t23-,24+,25+,26+,27-,28+,29+,30-,31-,32-,33-,34-,35-,36-,37-,38+,39+,40+,41+,42-,43-,44-,45-,46-,47-,48-,49-,50+,51-/m1/s1
comment: Pixatimod (PG545) is a heparan sulphate mimetic that acts as an inhibitor of the heparanase enzyme <Reference id=34630/><Reference id=34631/>. Structurally it is a cholestanol-conjugated sulfated oligosaccharide.
xref: CHEMBL2078841
synonym: PG545
synonym: PG-545
synonym: compound 18 [PMID: 22458531]
approved: f
ligand name: pixatimod
type: SyntheticOrganicLigand

branebrutinib
in ch i key: VJPPLCNBDLZIFG-ZDUSSCGKSA-N
in ch i: InChI=1S/C20H23FN4O2/c1-4-6-16(26)24-13-7-5-8-25(10-13)19-15(21)9-14(20(22)27)18-17(19)11(2)12(3)23-18/h9,13,23H,5,7-8,10H2,1-3H3,(H2,22,27)(H,24,26)/t13-/m0/s1
comment: Branebrutinib (BMS-986195) is a potent, covalent, irreversible inhibitor of the TEC family non-receptor tyrosine kinase, Bruton's tyrosine kinase (BTK) <Reference id=38164/>. BTK is essential in antigen-dependent B cell signaling and function, and is a therapeutic target for oncology and rheumatic diseases. Branebrutinib is a clinical lead for the treatment of rheumatoid arthritis, as claimed in Bristol-Myers Squibb's patent US20160115126A1 (Example 223) <Reference id=34617/>.
iupac name: 4-[(3S)-3-(but-2-ynoylamino)piperidin-1-yl]-5-fluoro-2,3-dimethyl-1H-indole-7-carboxamide
synonym: Example 223 [US20160115126A1]
synonym: BMS986195
synonym: BMS-986195
approved: f
ligand name: branebrutinib
type: SyntheticOrganicLigand

lofexidine
canonical SMILES: CC(C1=NCCN1)Oc1c(Cl)cccc1Cl
isomeric SMILES: CC(C1=NCCN1)Oc1c(Cl)cccc1Cl
in ch i key: KSMAGQUYOIHWFS-UHFFFAOYSA-N
in ch i: InChI=1S/C11H12Cl2N2O/c1-7(11-14-5-6-15-11)16-10-8(12)3-2-4-9(10)13/h2-4,7H,5-6H2,1H3,(H,14,15)
comment: Lofexidine is a selective α2-adrenoceptor agonist <Reference id=34614/>. The INN defines this drug as a racemic mixture of stereo isomers. We show the chemical structure without specified stereochemistry to represent the mixture. Oral lofexidine tablets contain the hydrochloride salt.
iupac name: 2-[1-(2,6-dichlorophenoxy)ethyl]-4,5-dihydro-1H-imidazole
xref: CHEMBL17860
synonym: BritLofex®
synonym: Lucemyra®
approved: t
ligand name: lofexidine
type: SyntheticOrganicLigand

TAK-828F
in ch i key: ICMFYVOUDGRBLG-VFHHBZAHSA-N
in ch i: InChI=1S/C28H32FN3O5/c1-28(2)8-6-16-13-18(14-20(29)24(16)28)30-26(35)25-19-4-5-22(37-3)31-21(19)7-9-32(25)27(36)17-10-15(11-17)12-23(33)34/h4-5,13-15,17,25H,6-12H2,1-3H3,(H,30,35)(H,33,34)/t15-,17+,25-/m1/s1
comment: TAK-828F is a potent, selective, and orally available novel retinoic acid receptor-related orphan receptor γt (RORγt) inverse agonist <Reference id=34599/><Reference id=34600/>. The X-ray structure of RORγt in complex with TAK-828F has been submitted to the Protein Data Bank (6BR3).
iupac name: 2-[3-[(5R)-5-[(7-fluoro-1,1-dimethyl-2,3-dihydroinden-5-yl)carbamoyl]-2-methoxy-7,8-dihydro-5H-1,6-naphthyridine-6-carbonyl]cyclobutyl]acetic acid
synonym: compound 10 [PMID: 29510038]
synonym: TAK828F
synonym: TAK-828
approved: f
ligand name: TAK-828F
type: SyntheticOrganicLigand

ozagrel
canonical SMILES: OC(=O)C=Cc1ccc(cc1)Cn1ccnc1
isomeric SMILES: OC(=O)/C=C/c1ccc(cc1)Cn1ccnc1
in ch i key: SHZKQBHERIJWAO-AATRIKPKSA-N
in ch i: InChI=1S/C13H12N2O2/c16-13(17)6-5-11-1-3-12(4-2-11)9-15-8-7-14-10-15/h1-8,10H,9H2,(H,16,17)/b6-5+
comment: Ozagrel is a thromboxane A synthetase (CYP5A1; TBXAS1) inhibitor that has anti-inflammatory action <Reference id=34598/>. Note that some of the bioactivity data for ozagrel relate to use of ozagrel sodium or ozagrel hydrochloride.
iupac name: 3-[4-(imidazol-1-ylmethyl)phenyl]prop-2-enoic acid
xref: CHEMBL11662
synonym: OKY-046
synonym: Pulmoza®
synonym: Cataclot®
synonym: KCT-0809
approved: t
ligand name: ozagrel
type: SyntheticOrganicLigand

revamilast
in ch i key: CFRXVFRHMZLQBS-UHFFFAOYSA-N
comment: Revamilast (GRC 4039) is an orally active, selective phosphodiesterase IV (PDE4) inhibitor, that was developed by Glenmark Pharmaceuticals for the treatment of multiple inflammatory conditions (rheumatoid arthritis (RA), asthma, chronic obstructive pulmonary disease (COPD) , multiple sclerosis, osteoarthritis, neuropathic pain). The chemical structure is claimed as Example 26 in Glenmark patent WO2006064355A2 <Reference id=34591/>. GRC 4039 is no longer listed on Glenmark's development pipeline webpage.
iupac name: N-(3,5-dichloro-1-hydroxypyridin-4-ylidene)-6-(difluoromethoxy)-[1]benzoxolo[3,2-c]pyridine-9-carboxamide
synonym: GRC 4039
synonym: GRC-4039
synonym: GRC4039
synonym: Example 26 [WO2006064355A2]
approved: f
ligand name: revamilast
type: SyntheticOrganicLigand

olafertinib
in ch i key: IDRGFNPZDVBSSE-UHFFFAOYSA-N
in ch i: InChI=1S/C29H28F2N6O2/c1-2-25(39)33-21-7-3-5-19(17-21)22-8-4-6-20-18-32-29(35-28(20)22)34-23-9-10-24(27(31)26(23)30)37-13-11-36(12-14-37)15-16-38/h2-10,17-18,38H,1,11-16H2,(H,33,39)(H,32,34,35)
comment: Olafertinib (CK‐101) is an orally available third-generation, selective inhibitor of epidermal growth factor receptor (EGFR) harbouring activating mutations (e.g. the resistance mutation T790M, the L858R mutation and the exon 19 deletion (del 19) mutation). It is an irreversible (covalent binding) inhibitor with minimal activity towards the wild type EGFR. The chemical structure is claimed as Example 153 in patent US20170050936A1 <Reference id=34576/>.
synonym: CK101
synonym: RX518
synonym: RX-518
synonym: Example 153 [US20170050936A1]
synonym: CK‐101
approved: f
ligand name: olafertinib
type: SyntheticOrganicLigand

poseltinib
in ch i key: LZMJNVRJMFMYQS-UHFFFAOYSA-N
in ch i: InChI=1S/C26H26N6O3/c1-3-23(33)27-19-5-4-6-21(17-19)35-25-24-22(11-16-34-24)29-26(30-25)28-18-7-9-20(10-8-18)32-14-12-31(2)13-15-32/h3-11,16-17H,1,12-15H2,2H3,(H,27,33)(H,28,29,30)
comment: Poseltinib (HM71224) is an inhibitor of Bruton's tyrosine kinase (BTK). Having shown anti-inflammatory activity in rodent models of rheumatoid arthritis (RA) and SLE <Reference id=34574/><Reference id=31022/><Reference id=34573/>, it was advanced to clinical trial as a potential RA therapy. The chemical structure is claimed in Hanmi patent WO2011162515A2 <Reference id=34574/> (Example 228).
iupac name: N-[3-[2-[4-(4-methylpiperazin-1-yl)anilino]furo[3,2-d]pyrimidin-4-yl]oxyphenyl]prop-2-enamide
synonym: HM‐71224
synonym: LY333764
synonym: HM71224
synonym: Example 228 [WO2011162515A2]
approved: f
ligand name: poseltinib
type: SyntheticOrganicLigand

zanubrutinib
in ch i key: RNOAOAWBMHREKO-QFIPXVFZSA-N
in ch i: InChI=1S/C27H29N5O3/c1-2-23(33)31-16-13-18(14-17-31)22-12-15-29-27-24(26(28)34)25(30-32(22)27)19-8-10-21(11-9-19)35-20-6-4-3-5-7-20/h2-11,18,22,29H,1,12-17H2,(H2,28,34)/t22-/m0/s1
comment: Zanubrutinib (BGB-3111) is a potent, selective and irreversible BTK inhibitor that was developed by BeiGene for utility in the treatment of B cell cancers, such as non-Hodgkin's lymphoma and chronic lymphocytic leukemia (CLL) <Reference id=34570/><Reference id=34571/>.
iupac name: (7S)-2-(4-phenoxyphenyl)-7-(1-prop-2-enoylpiperidin-4-yl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine-3-carboxamide
xref: CHEMBL3936761
synonym: Brukinsa®
synonym: compound 27b [US9447106]
synonym: BGB-3111
synonym: BGB3111
approved: t
ligand name: zanubrutinib
type: SyntheticOrganicLigand

vidofludimus
in ch i key: XPRDUGXOWVXZLL-UHFFFAOYSA-N
in ch i: InChI=1S/C20H18FNO4/c1-26-14-5-2-4-12(10-14)13-8-9-18(17(21)11-13)22-19(23)15-6-3-7-16(15)20(24)25/h2,4-5,8-11H,3,6-7H2,1H3,(H,22,23)(H,24,25)
comment: Vidofludimus (4SC-101) is a small molecule dihydroorotate dehydrogenase (DHOD) inhibitor that was developed for immunosuppressive potential <Reference id=34561/>. It has an improved toxicity profile in comparison to the clinically used disease modifying anti-rheumatic drug (DMARD) <Ligand id=6825/>. Since its initial development, vidofludimus has been superceded by IMU-838 which is an orally active polymorph of vidofludimus calcium (PubChem CID: 56944639) <Reference id=40042/>.<br SARS-CoV-2 and COVID-19: The target of vidofludimus, DHODH, plays a role in the metabolism of activated T cells and B cells to regulate the inflammatory response. It has been advanced to clinical trial in patients with severe COVID-19, to as attempt to block the release of pro-inflammatory cytokines and temper hyperinflammation in these patients.
iupac name: 2-[[2-fluoro-4-(3-methoxyphenyl)phenyl]carbamoyl]cyclopentene-1-carboxylic acid
xref: CHEMBL197194
synonym: 4SC-101
synonym: SC12267
synonym: IMU-838 (vidofludimus calcium)
approved: f
ligand name: vidofludimus
type: SyntheticOrganicLigand

GS-458967
in ch i key: FEVBKJITJDHASC-UHFFFAOYSA-N
in ch i: InChI=1S/C14H7F6N3O/c15-13(16,17)12-22-21-11-6-3-9(7-23(11)12)8-1-4-10(5-2-8)24-14(18,19)20/h1-7H
comment: Late sodium current inhibitor (Late INai) of the cardiac NaV1.5 channel <Reference id=34553/>. A May 2018 BJP paper indicates GS-458967 suppresses Torsades de Pointes (this was an author prepublication alert for a new ligand entry). The Gilhead patent has % inhibition data for 355 analogues <Reference id=35007/>.
iupac name: 6-[4-(trifluoromethoxy)phenyl]-3-(trifluoromethyl)-[1,2,4]triazolo[4,3-a]pyridine
synonym: GS967
approved: f
ligand name: GS-458967
type: SyntheticOrganicLigand

BMS-986142
in ch i key: ZRYMMWAJAFUANM-INIZCTEOSA-N
in ch i: InChI=1S/C32H30F2N4O4/c1-15-17(7-6-10-24(15)38-30(40)19-8-5-9-21(33)28(19)37(4)31(38)41)25-22(34)14-20(29(35)39)27-26(25)18-12-11-16(32(2,3)42)13-23(18)36-27/h5-10,14,16,36,42H,11-13H2,1-4H3,(H2,35,39)/t16-/m0/s1
comment: BMS-986142 is a potent, highly selective and reversible small molecule BTK inhibitor <Reference id=34545/><Reference id=34546/>, that is being investigated for anti-inflammatory potential <Reference id=34547/>.
iupac name: (7S)-3-fluoro-4-[3-(8-fluoro-1-methyl-2,4-dioxoquinazolin-3-yl)-2-methylphenyl]-7-(2-hydroxypropan-2-yl)-6,7,8,9-tetrahydro-5H-carbazole-1-carboxamide
synonym: BMS986142
synonym: compound 14f [PMID: 27583770]
approved: f
ligand name: BMS-986142
type: SyntheticOrganicLigand

rabeximod
in ch i key: PDNNUMNEXITLCZ-UHFFFAOYSA-N
in ch i: InChI=1S/C22H24ClN5O/c1-13-9-17-18(10-14(13)2)26-22-21(25-17)16-11-15(23)5-6-19(16)28(22)12-20(29)24-7-8-27(3)4/h5-6,9-11H,7-8,12H2,1-4H3,(H,24,29)
comment: Rabeximod is an orally active immunomodulator. It has potent anti-rheumatic effects in animal models and is being evaluated as a potential drug for rheumatoid arthritis patients. The structure was originally claimed in patent WO2005123741A1 (Compound E) for anti-inflammatory potential <Reference id=34532/>, and later for antiviral potential in patent WO2014140321A1 (example 2). The molecular mechanism of action of this compound vis its anti-inflammatory activity remains unclear.
iupac name: 2-(9-chloro-2,3-dimethylindolo[3,2-b]quinoxalin-6-yl)-N-[2-(dimethylamino)ethyl]acetamide
synonym: Rob 803
synonym: Rob-803
synonym: Rob803
approved: f
ligand name: rabeximod
type: SyntheticOrganicLigand

petesicatib
in ch i key: KXAAIORSMACJSI-AEFFLSMTSA-N
comment: Petesicatib is the INN for a cathepsin S inhibitor. The structure (and CAS registry number) submitted to the WHO match PubChem CID 59543597, and this ties the INN together with the research code RO5459072 assigned by Hoffman-La Roche to their cathepsin S inhibitor <Reference id=34527/><Reference id=34528/>. This same chemical structure is claimed in Hoffmann-La Roche patent WO2010121918A1, where it is example 238 <Reference id=34529/>.
synonym: RO-5459072
synonym: RG7625
synonym: RG-7625
approved: f
ligand name: petesicatib
type: SyntheticOrganicLigand

MK-0873
in ch i key: JJWKQXNHYDJXKF-UHFFFAOYSA-N
in ch i: InChI=1S/C25H18N4O3/c30-23-21-7-2-12-26-24(21)29(16-22(23)25(31)27-19-10-11-19)20-6-1-4-17(14-20)8-9-18-5-3-13-28(32)15-18/h1-7,12-16,19H,10-11H2,(H,27,31)
comment: MK-0873 is an optimized investigational PDE4 inhibitor with favourable in vitro and in vivo profiles that support clinical development <Reference id=34522/>.
iupac name: N-cyclopropyl-1-[3-[2-(1-oxidopyridin-1-ium-3-yl)ethynyl]phenyl]-4-oxo-1,8-naphthyridine-3-carboxamide
xref: CHEMBL485629
synonym: compound 20 [PMID: 18835163]
synonym: MK0873
synonym: MK 0873
approved: f
ligand name: MK-0873
type: SyntheticOrganicLigand

MK-0359
in ch i key: YYGZHVJDHMMABU-OGLMXYFKSA-N
in ch i: InChI=1S/C31H29N3O5S2/c1-20-33-30(39-34-20)28(22-11-13-26(14-12-22)40(4,35)36)17-21-8-6-9-23(16-21)27-19-25(31(2,3)41(5,37)38)18-24-10-7-15-32-29(24)27/h6-19H,1-5H3/b28-17+
comment: MK-0359 is a potent and selective, oral PDE4 inhibitor that has a competitive and reversible mode of interaction. MK-0359 is identified as L-454,560 <Reference id=34519/> by citation in <Reference id=34520/>. MK-0359 inhibits both the apo- (Mg2+ free) and holoenzyme ((Mg2+-bound) states of PDE4 <Reference id=34519/>.
iupac name: 3-methyl-5-[(E)-1-(4-methylsulfonylphenyl)-2-[3-[6-(2-methylsulfonylpropan-2-yl)quinolin-8-yl]phenyl]ethenyl]-1,2,4-oxadiazole
xref: CHEMBL372575
synonym: MK0359
synonym: L-454560
synonym: L-454,560
approved: f
ligand name: MK-0359
type: SyntheticOrganicLigand

LX2931
canonical SMILES: CC(=c1[nH]c(c[nH]1)C(C(C(CO)O)O)O)N=O
in ch i key: CGJLPLVZAAEKTK-LIVYHJONSA-N
in ch i: InChI=1S/C9H15N3O5/c1-4(12-17)9-10-2-5(11-9)7(15)8(16)6(14)3-13/h2,6-8,10-11,13-16H,3H2,1H3/b9-4+/t6-,7-,8-/m1/s1
comment: LX2931 (LX3305) is a first-in-class, orally available, functional S1P lyase inhibitor, that has been investigated for anti-inflammatory potential <Reference id=34512/>. Note that LX2931 does not block S1PL catalytic activity in a biochemical assay even at 100 μM <Reference id=28158/>.
iupac name: (1R,2S,3R)-1-[(2E)-2-(1-nitrosoethylidene)-1,3-dihydroimidazol-4-yl]butane-1,2,3,4-tetrol
xref: CHEMBL1852164
synonym: LX3305
approved: f
ligand name: LX2931
type: SyntheticOrganicLigand

GW406381
in ch i key: NXMZBNYLCVTRGB-UHFFFAOYSA-N
in ch i: InChI=1S/C21H19N3O3S/c1-3-27-17-10-6-16(7-11-17)21-20(19-5-4-14-22-24(19)23-21)15-8-12-18(13-9-15)28(2,25)26/h4-14H,3H2,1-2H3
comment: GW406381 is a cyclooxygenase inhibitor that is selective for the COX2 isozyme, that has clinical potential for the treatment of inflammatory pain <Reference id=34509/>.
iupac name: 2-(4-ethoxyphenyl)-3-(4-methylsulfonylphenyl)pyrazolo[5,1-f]pyridazine
xref: CHEMBL364804
synonym: GW-406381
synonym: GW 406381
synonym: compound 8 [PMID: 15454242]
approved: f
ligand name: GW406381
type: SyntheticOrganicLigand

GW274150
canonical SMILES: CC(=NCCSCCC(C(=O)O)N)N
isomeric SMILES: CC(=NCCSCC[C@@H](C(=O)O)N)N
in ch i key: MOLOJNHYNHBPCW-ZETCQYMHSA-N
in ch i: InChI=1S/C8H17N3O2S/c1-6(9)11-3-5-14-4-2-7(10)8(12)13/h7H,2-5,10H2,1H3,(H2,9,11)(H,12,13)/t7-/m0/s1
comment: GW274150 is a selective inducible nitric oxide synthase (iNOS) inhibitor that is active in vitro and in vivo <Reference id=34501/>.
iupac name: (2S)-2-amino-4-[2-(1-aminoethylideneamino)ethylsulfanyl]butanoic acid
xref: CHEMBL114551
synonym: GW-274150
synonym: [2-[(1-iminoethyl) amino]ethyl]-L-homocysteine
approved: f
ligand name: GW274150
type: SyntheticOrganicLigand

Galapagos MAPKAPK5 inhibitor D
in ch i key: DLGZLIXYVSQGOX-UHFFFAOYSA-N
in ch i: InChI=1S/C24H28N8O2/c1-24(2,3)31-10-8-30(9-11-31)18-6-4-17(5-7-18)29-22-23-27-15-28-32(23)19(13-26-22)16-12-20(21(25)33)34-14-16/h4-7,12-15H,8-11H2,1-3H3,(H2,25,33)(H,26,29)
comment: This compound was developed by Galapagos as a MAPKAPK5 inhibitor, in the search for a novel anti-inflammatory mechanism that would be applicable to the treatment of rheumatoid arthritis (RA). The discovery pathway is detailed in the pdf entitled 'Discovery of inhibitors of MAPKAPK5, a novel target for rheumatoid arthritis', which is available online here. The chemical structure is claimed in Galapagos patent WO2007138072A2, as compound 183 <Reference id=34500/>. This compound (compound D) is likely to be a relation of the Galapagos clinical candidate GLPG0259, which failed in Phase 2 clinical trial in patients with <Ligand id=4815/>-refractory RA <Reference id=34497/>.
iupac name: 4-[8-[4-(4-tert-butylpiperazin-1-yl)anilino]-[1,2,4]triazolo[1,5-a]pyrazin-5-yl]furan-2-carboxamide
synonym: compound 183 [WO2007138072A2]
approved: f
ligand name: Galapagos MAPKAPK5 inhibitor D
type: SyntheticOrganicLigand

CR6086
in ch i key: CADWTPLFEZSAHM-OAQYLSRUSA-N
in ch i: InChI=1S/C26H27F3N2O3/c27-26(28,29)20-5-1-17(2-6-20)16-31-14-13-24(9-10-24)15-21(31)22(32)30-25(11-12-25)19-7-3-18(4-8-19)23(33)34/h1-8,21H,9-16H2,(H,30,32)(H,33,34)/t21-/m1/s1
comment: CR6086 is a potent and selective prostaglandin E2 receptor 4 (EP4) antagonist that that is being investigated for immunomodulatory potential, that may be suitable for the treatment of rheumatoid arthritis <Reference id=34489/>.
iupac name: 4-{1-[(5R)-6-{[4-(trifluoromethyl)phenyl]methyl}-6-azaspiro[2.5]octane-5-amido]cyclopropyl}benzoic acid
approved: f
ligand name: CR6086
type: SyntheticOrganicLigand

CH-4051
in ch i key: NAWXUBYGYWOOIX-SFHVURJKSA-N
in ch i: InChI=1S/C23H23N5O5/c1-12(21(30)31)10-18(22(32)33)26-20(29)15-7-4-13(5-8-15)2-3-14-6-9-17-16(11-14)19(24)28-23(25)27-17/h4-9,11,18H,1-3,10H2,(H,26,29)(H,30,31)(H,32,33)(H4,24,25,27,28)/t18-/m0/s1
comment: CH-4051 is an orally available <Ligand id=4815/> (MTX) analogue that is designed to resist metabolic degradation <Reference id=34488/><Reference id=34487/>. This strategy was employed to improve the safety and tolerability profile compared to MTX, since a significant proportion of the toxicity profile of MTX can be attributed to its polyglutamylated and hydroxylated metabolites. Like MTX, CH-4051 has anti-inflammatory, autoimmune and anti-tumour properties and is a potent inhibitor of dihydrofolate reductase, an enzyme required for cell proliferation. The racemic mixture of CH-4051, known as CH-1405 (represented by the non-chiral structure in PubChem CID 9846537) <Reference id=34484/>, completed Phase 2 development for rheumatoid arthritis, and exhibited comparable efficacy to MTX <Reference id=34485/><Reference id=34486/>. Structurally, CH-4051 is the more active L-4'-methylene-glutamic acid containing diastereomer (or S-enantiomer) of CH-1405 <Reference id=34487/>.
iupac name: (2S)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid
synonym: Formula (10) [WO2012078708A1]
approved: f
ligand name: CH-4051
type: SyntheticOrganicLigand

agatolimod
in ch i key: GUVMFDICMFQHSZ-UHFFFAOYSA-N
comment: Agatolimod is synthetic CpG oligodeoxynucleotide that acts as a TLR9 agonist <Reference id=34480/>. We show the parent molecule, whereas the USAN specifies agatolimod sodium (PubChem CID 56841789), and the synonyms we list may also refer to the sodium congener. Its nucleotide sequence is d(P-thio)(T-C-G-T-C-G-T-T-T-T-G-T-C-G-T-T-T-T-G-T-C-G-T-T).
synonym: ProMune
synonym: PF-3512676
synonym: CpG7909
synonym: CpG 7909
synonym: PF 3512676
synonym: PF3512676
synonym: VaxImmune
approved: f
ligand name: agatolimod
type: SyntheticOrganicLigand

compound 19a [PMID: 26506089]
in ch i key: CGLGRSOJPUXNFA-YVXBOAIISA-N
in ch i: InChI=1S/C33H37IN3O7P/c1-22(23-12-18-27(19-13-23)44-45(41,42)43)21-29(38)35-30(33(2,3)4)32(40)36-20-8-11-28(36)31(39)37(25-9-6-5-7-10-25)26-16-14-24(34)15-17-26/h5-7,9-10,12-19,21,28,30H,8,11,20H2,1-4H3,(H,35,38)(H2,41,42,43)/b22-21+/t28-,30+/m0/s1
comment: Compound 19a is the most potent of a series of STAT6 inhibitors reported by Mandal et al. (2015) <Reference id=34465/>. STAT6 inhibitors are being developed for their potential to inhibit the expression of genes contributing to asthma. Compound 19a is a phosphopeptide mimic that blocks interaction of the IL-4 and IL-13 receptors with the SH2 domain of STAT6, thereby preventing the downstream transcriptional sequelae of STAT6 activation. The structure is claimed in patent WO2014182928 <Reference id=34471/>.
iupac name: [4-[(E)-4-[[(2S)-1-[(2S)-2-[(4-iodophenyl)-phenylcarbamoyl]pyrrolidin-1-yl]-3,3-dimethyl-1-oxobutan-2-yl]amino]-4-oxobut-2-en-2-yl]phenyl] dihydrogen phosphate
xref: CHEMBL3741938
approved: f
ligand name: compound 19a [PMID: 26506089]
type: SyntheticOrganicLigand

merestinib
in ch i key: QHADVLVFMKEIIP-UHFFFAOYSA-N
in ch i: InChI=1S/C30H22F2N6O3/c1-17-3-9-23(30(40)38(17)22-7-4-20(31)5-8-22)29(39)36-21-6-10-27(25(32)12-21)41-28-11-18-16-35-37(2)26(18)13-24(28)19-14-33-34-15-19/h3-16H,1-2H3,(H,33,34)(H,36,39)
comment: Merestinib (LY2801653) is a type II ATP-competitive multikinase inhibitor <Reference id=34467/>. It inhibits several kinases including the oncokinases MET (the hepatocyte growth factor [HGF] receptor), RON (MST1R), AXL, MERTK, MKNK1/2, and Tie2/TEK. Merestinib exhibits anti-tumour activity in vitro and in vivo and is orally available.
iupac name: N-[3-fluoro-4-[1-methyl-6-(1H-pyrazol-4-yl)indazol-5-yl]oxyphenyl]-1-(4-fluorophenyl)-6-methyl-2-oxopyridine-3-carboxamide
xref: CHEMBL3545307
synonym: LY2801653
synonym: LY-2801653
approved: f
ligand name: merestinib
type: SyntheticOrganicLigand

SR7826
in ch i key: WQAGVQVBDHOHRD-UHFFFAOYSA-N
in ch i: InChI=1S/C22H21N5O2/c1-15-13-23-21-19(15)20(24-14-25-21)16-7-9-17(10-8-16)26-22(29)27(11-12-28)18-5-3-2-4-6-18/h2-10,13-14,28H,11-12H2,1H3,(H,26,29)(H,23,24,25)
comment: Potent and selective LIMK inhibitor.
iupac name: 1-(2-hydroxyethyl)-3-[4-(5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)phenyl]-1-phenylurea
synonym: SR 7826
approved: f
ligand name: SR7826
type: SyntheticOrganicLigand

LIMKi3
in ch i key: IVUGBSGLHRJSSP-UHFFFAOYSA-N
comment: Potent LIM kinase inhibitor.
iupac name: N-[5-[2-(2,6-dichlorophenyl)-5-(difluoromethyl)pyrazol-3-yl]-1,3-thiazol-2-yl]-2-methylpropanamide
synonym: LIMKi 3
synonym: BMS-5
synonym: BMS 5
approved: f
ligand name: LIMKi3
type: SyntheticOrganicLigand

CGP37849
canonical SMILES: CC(=CC(C(=O)O)N)CP(=O)(O)O
isomeric SMILES: C/C(=C/C(C(=O)O)N)/CP(=O)(O)O
in ch i key: BDYHNCZIGYIOGJ-DUXPYHPUSA-N
in ch i: InChI=1S/C6H12NO5P/c1-4(3-13(10,11)12)2-5(7)6(8)9/h2,5H,3,7H2,1H3,(H,8,9)(H2,10,11,12)/b4-2+
iupac name: (E)-2-amino-4-methyl-5-phosphonopent-3-enoic acid
xref: CHEMBL29811
synonym: CGP 37849
synonym: CGP-37849
approved: f
ligand name: CGP37849
type: SyntheticOrganicLigand

UFP-505
in ch i key: SYOVEDOWOXNOJG-SVBPBHIXSA-N
in ch i: InChI=1S/C30H34N4O4/c1-19-12-24(35)13-20(2)25(19)15-26(31)30(38)34-18-23-11-7-6-10-22(23)14-27(34)29(37)33-17-28(36)32-16-21-8-4-3-5-9-21/h3-13,26-27,35H,14-18,31H2,1-2H3,(H,32,36)(H,33,37)/t26-,27-/m0/s1
comment: Potent MOPR agonist and DOPR antagonist; a MOP/DOP bifunctional opioid.
iupac name: (3S)-2-[(2S)-2-amino-3-(4-hydroxy-2,6-dimethylphenyl)propanoyl]-N-[2-oxo-2-(phenylmethylamino)ethyl]-3,4-dihydro-1H-isoquinoline-3-carboxamide
xref: CHEMBL458631
synonym: H-Dmt-Tic-Gly-NH-Bzl
approved: f
ligand name: UFP-505
type: SyntheticOrganicLigand

CZ415
in ch i key: AQEVFCKBHLCDIP-INIZCTEOSA-N
in ch i: InChI=1S/C24H33N5O2S/c1-7-25-23(30)26-18-10-8-17(9-11-18)21-27-20-19(15-32(5,6)24(20,3)4)22(28-21)29-12-13-31-14-16(29)2/h8-11,16H,5-7,12-15H2,1-4H3,(H2,25,26,30)/t16-/m0/s1
comment: CZ415 is a potent and selective, ATP-competitive mTOR inhibitor that has potential anti-inflammatory activity <Reference id=34453/>.
iupac name: 1-(4-{7,7-dimethyl-6,6-dimethylidene-4-[(3S)-3-methylmorpholin-4-yl]-5H,7H-6λ⁶-thieno[3,4-d]pyrimidin-2-yl}phenyl)-3-ethylurea
synonym: CZ-415
synonym: CZ 415
synonym: compound 3 [PMID: 27563401]
approved: f
ligand name: CZ415
type: SyntheticOrganicLigand

tanzisertib
in ch i key: IBGLGMOPHJQDJB-MOKVOYLWSA-N
in ch i: InChI=1S/C21H23F3N6O2/c22-11-7-15(23)18(16(24)8-11)28-21-27-17-9-25-20(26-12-1-3-14(31)4-2-12)29-19(17)30(21)13-5-6-32-10-13/h7-9,12-14,31H,1-6,10H2,(H,27,28)(H,25,26,29)/t12?,13-,14?/m0/s1
comment: Tanzisertib (CC-930) is a potent, selective, and orally active first generation JNK inhibitor <Reference id=34451/>. It inhibits JNK1/2 but with a JNK2 bias. Tanzisertib is being investigated for potential antifibrotic activity based on preclinical evidence that JNK enzyme function is required for key steps in the pulmonary fibrotic process. Preventing/reducing fibrosis represents a more favourable treatment modality that offered by current therapies for idiopathic pulmonary fibrosis which delay the loss of lung function but do not stabilise and/or reverse fibrotic tissue damage.
xref: CHEMBL1950289
synonym: CC930
synonym: CC 930
synonym: compound 1 [PMID: 22244937]
synonym: CC-930
approved: f
ligand name: tanzisertib
type: SyntheticOrganicLigand

compound 5b [PMID: 29457898]
in ch i key: OAOYKSGPQULCDH-WHZCJLAPSA-N
in ch i: InChI=1S/C27H40NO6PSi/c1-22(20-33-36(6,7)27(3,4)5)18-19-32-35(30,34-25-16-12-9-13-17-25)28-23(2)26(29)31-21-24-14-10-8-11-15-24/h8-18,23H,19-21H2,1-7H3,(H,28,30)/b22-18+/t23-,35?/m0/s1
comment: Vβ9/Vδ2 T-cells have been shown to be activated by small molecule phosphoantigens (PAgs). The aryloxy triester phosphoramidate prodrug ProPAgen 5b is a potent and specific activator of these cells as a potential immunotherapeutic agent <Reference id=34448/>. The molecular mechanism of action is unkown but evidence supports PAgs binding the intracellular B30.2 domain of butyrophilin 3A1.
iupac name: Benzyl ((((E)-4-((tert-Butyldimethylsilyl)oxy)-3-methylbut-2-en-1-yl)oxy)(phenoxy)phosphoryl)-L-alaninate
approved: f
ligand name: compound 5b [PMID: 29457898]
type: SyntheticOrganicLigand

bufuralol
canonical SMILES: CCc1cccc2c1oc(c2)C(CNC(C)(C)C)O
isomeric SMILES: CCc1cccc2c1oc(c2)C(CNC(C)(C)C)O
in ch i key: SSEBTPPFLLCUMN-UHFFFAOYSA-N
in ch i: InChI=1S/C16H23NO2/c1-5-11-7-6-8-12-9-14(19-15(11)12)13(18)10-17-16(2,3)4/h6-9,13,17-18H,5,10H2,1-4H3
comment: Potent beta-adrenoceptor antagonist, which is metabolized by CYP2D6.
iupac name: 2-(tert-butylamino)-1-(7-ethyl-1-benzofuran-2-yl)ethanol
xref: CHEMBL296035
approved: f
ligand name: bufuralol
type: SyntheticOrganicLigand

[18F]PF-06684511
in ch i key: YZXTXNWZTAVDKH-LRFGSCOBSA-N
comment: <Ligand id=9831/> with high specific binding to BACE1 in brain, upon radiolabeling with [18F] demonstrated favourable uptake and high in vivo specificity in nonhuman primate, suggesting its potential for imaging BACE1 in vivo <Reference id=34415/>.
iupac name: N-[3-[(4aS,5S,7aS)-2-amino-5-(fluoromethyl)-4,4a,5,7-tetrahydrofuro[3,4-d][1,3]thiazin-7a-yl]-4-fluorophenyl]-5-methoxypyrazine-2-carboxamide
approved: f
ligand name: [18F]PF-06684511
type: SyntheticOrganicLigand

PF-06684511
in ch i key: YZXTXNWZTAVDKH-KPAZRMRSSA-N
comment: Using a set of PET ligand design parameters, compound 3 (PF-06684511) was rapidly identified as a lead with favorable in vitro attributes and structural handles for PET radiolabeling. Further evaluation in a LC-MS/MS cold tracer study in rodents revealed high specific binding to BACE1 in brain. Upon radiolabeling, [18F]3 demonstrated favorable brain uptake and high in vivo specificity in nonhuman primates (NHP), suggesting its potential for imaging BACE1 in humans <Reference id=34415/>.
iupac name: N-[3-[(4aS,5S,7aS)-2-amino-5-(fluoromethyl)-4,4a,5,7-tetrahydrofuro[3,4-d][1,3]thiazin-7a-yl]-4-fluorophenyl]-5-methoxypyrazine-2-carboxamide
approved: f
ligand name: PF-06684511
type: SyntheticOrganicLigand

sulfanegen
canonical SMILES: OC(=O)C1(O)SCC(SC1)(O)C(=O)O
isomeric SMILES: OC(=O)C1(O)SCC(SC1)(O)C(=O)O
in ch i key: GYZMXMSJOZUNEQ-UHFFFAOYSA-N
in ch i: InChI=1S/C6H8O6S2/c7-3(8)5(11)1-13-6(12,2-14-5)4(9)10/h11-12H,1-2H2,(H,7,8)(H,9,10)
comment: Sulfanegen is an experimental antidote for cyanide poisoning as a prodrug for <Ligand id=5118/> <Reference id=34403/>. Note the common representations are for the unresolved racemate (see 'same connectivity' in PubChem) and the sodium salt PubChem CID 68973741.
iupac name: 2,5-dihydroxy-1,4-dithiane-2,5-dicarboxylic acid
xref: CHEMBL2316231
approved: f
ligand name: sulfanegen
type: SyntheticOrganicLigand

geldanamycin
in ch i key: QTQAWLPCGQOSGP-KSRBKZBZSA-N
in ch i: InChI=1S/C29H40N2O9/c1-15-11-19-25(34)20(14-21(32)27(19)39-7)31-28(35)16(2)9-8-10-22(37-5)26(40-29(30)36)18(4)13-17(3)24(33)23(12-15)38-6/h8-10,13-15,17,22-24,26,33H,11-12H2,1-7H3,(H2,30,36)(H,31,35)/b10-8-,16-9+,18-13+/t15-,17+,22+,23+,24-,26+/m1/s1
comment: Geldanamycin is a benzoquinone antibacterial that inhibits HSP90 and promotes the proteasomal degradation of oncogenic signaling proteins.
iupac name: [(3R,5S,6R,7S,8E,10S,11S,12Z,14E)-6-hydroxy-5,11,21-trimethoxy-3,7,9,15-tetramethyl-16,20,22-trioxo-17-azabicyclo[16.3.1]docosa-1(21),8,12,14,18-pentaen-10-yl] carbamate
xref: CHEMBL278315
approved: f
ligand name: geldanamycin
type: SyntheticOrganicLigand

alvespimycin
in ch i key: KUFRQPKVAWMTJO-LMZWQJSESA-N
in ch i: InChI=1S/C32H48N4O8/c1-18-14-22-27(34-12-13-36(5)6)24(37)17-23(29(22)39)35-31(40)19(2)10-9-11-25(42-7)30(44-32(33)41)21(4)16-20(3)28(38)26(15-18)43-8/h9-11,16-18,20,25-26,28,30,34,38H,12-15H2,1-8H3,(H2,33,41)(H,35,40)/b11-9-,19-10+,21-16+/t18-,20+,25+,26+,28-,30+/m1/s1
comment: Alvespimycin is an analogue of the antineoplastic benzoquinone antibacterial <Ligand id=9829/>, a heat shock protein (HSP) 90 inhibitor. It has been used in trials studying the treatment of solid tumours in various cancers. It has particularly complex stereochemistry with 45 'same-connectivity' relationships in PubChem.
iupac name: [(3R,5S,6R,7S,8E,10S,11S,12Z,14E)-21-[2-(dimethylamino)ethylamino]-6-hydroxy-5,11-dimethoxy-3,7,9,15-tetramethyl-16,20,22-trioxo-17-azabicyclo[16.3.1]docosa-1(21),8,12,14,18-pentaen-10-yl] carbamate
xref: CHEMBL383824
synonym: 17-DMAG
approved: f
ligand name: alvespimycin
type: SyntheticOrganicLigand

retaspimycin hydrochloride
in ch i key: OIRUWDYJGMHDHJ-AFXVCOSJSA-N
in ch i: InChI=1S/C31H45N3O8.ClH/c1-8-12-33-26-21-13-17(2)14-25(41-7)27(36)19(4)15-20(5)29(42-31(32)39)24(40-6)11-9-10-18(3)30(38)34-22(28(21)37)16-23(26)35;/h8-11,15-17,19,24-25,27,29,33,35-37H,1,12-14H2,2-7H3,(H2,32,39)(H,34,38);1H/b11-9-,18-10+,20-15+;/t17-,19+,24+,25+,27-,29+;/m1./s1
comment: 17-Allylamino-17-demethoxygeldanamycin (17-AAG)1 is a semisynthetic inhibitor of the 90 kDa heat shock protein (Hsp90) currently in clinical trials for the treatment of cancer. However, 17-AAG faces challenging formulation issues due to its poor solubility. The synthesis and evaluation of a highly soluble hydroquinone hydrochloride derivative of 17-AAG, 1a (IPI-504) was reported in <Reference id=34398/>. A Phase I trial indicated this was well-tolerated with some evidence of antitumor activity, serving as a clinical proof-of-concept that HSP90 inhibition remains promising <Reference id=34399/>. Note this ligand entry is an exception to our general rule of salt-stripping because it is clear in this case that the hydorchoride is being used. The parent structure is PubChem CID 11534420.
iupac name: [(3R,5S,6R,7S,8E,10S,11S,12Z,14E)-6,20,22-trihydroxy-5,11-dimethoxy-3,7,9,15-tetramethyl-16-oxo-21-(prop-2-enylamino)-17-azabicyclo[16.3.1]docosa-1(22),8,12,14,18,20-hexaen-10-yl] carbamate;hydrochloride
synonym: IPI504
synonym: IPI-504
synonym: 17-Allylamino-17-demethoxygeldanamycin (hydrochloride)
synonym: 17-AAG (hydrochloride)
approved: f
ligand name: retaspimycin hydrochloride
type: SyntheticOrganicLigand

butoxamine
canonical SMILES: COc1ccc(cc1C(C(NC(C)(C)C)C)O)OC
isomeric SMILES: COc1ccc(cc1C(C(NC(C)(C)C)C)O)OC
in ch i key: TWUSDDMONZULSC-UHFFFAOYSA-N
in ch i: InChI=1S/C15H25NO3/c1-10(16-15(2,3)4)14(17)12-9-11(18-5)7-8-13(12)19-6/h7-10,14,16-17H,1-6H3
comment: beta-2 selective adrenergic antagonist
iupac name: 2-(tert-butylamino)-1-(2,5-dimethoxyphenyl)propan-1-ol
xref: CHEMBL289093
approved: f
ligand name: butoxamine
type: SyntheticOrganicLigand

GSK1059615
isomeric SMILES: O=C1NC(=O)/C(=C/c2ccc3c(c2)c(ccn3)c2ccncc2)/S1
in ch i key: QDITZBLZQQZVEE-YBEGLDIGSA-N
in ch i: InChI=1S/C18H11N3O2S/c22-17-16(24-18(23)21-17)10-11-1-2-15-14(9-11)13(5-8-20-15)12-3-6-19-7-4-12/h1-10H,(H,21,22,23)/b16-10-
comment: GSK1059615 is a PI3K and mTOR dual inhibitor <Reference id=30404/>. Some data on this compound is nested in a paper characterising GSK2126458 that we have as Omipalisib. GSK1059615 was later reported to inhibited survival and proliferation of established (SCC-9, SQ20B and A253 lines) and primary human HNSCC cells, possibly the latter via programmed necrosis pathway <Reference id=34397/> . However,a Phase 1 dose-escalation study against solid tumors or lymphoma was terminated prematurely (July 2017) due to lack of sufficient exposure.
iupac name: (5Z)-5-[(4-pyridin-4-ylquinolin-6-yl)methylidene]-1,3-thiazolidine-2,4-dione
xref: CHEMBL3544966
approved: f
ligand name: GSK1059615
type: SyntheticOrganicLigand

compound 3b [PMID:28943244]
canonical SMILES: COc1ccccc1N1CCN(CC1)CCNC(=O)c1ccccn1
isomeric SMILES: COc1ccccc1N1CCN(CC1)CCNC(=O)c1ccccn1
in ch i key: ARQDTTRYUMUINH-UHFFFAOYSA-N
in ch i: InChI=1S/C19H24N4O2/c1-25-18-8-3-2-7-17(18)23-14-12-22(13-15-23)11-10-21-19(24)16-6-4-5-9-20-16/h2-9H,10-15H2,1H3,(H,21,24)
comment: A range of picolinamide derivatives, linked to an arylpiperazine moiety, were prepared and their affinity to 5-HT1A, 5-HT2A and 5-HT2C receptors determined. Compound 3b showed subnanomolar affinity towards 5-HT2A <Reference id=34396/>.
iupac name: N-[2-[4-(2-methoxyphenyl)piperazin-1-yl]ethyl]pyridine-2-carboxamide
approved: f
ligand name: compound 3b [PMID:28943244]
type: SyntheticOrganicLigand

cenerimod
in ch i key: KJKKMMMRWISKRF-FQEVSTJZSA-N
in ch i: InChI=1S/C25H31N3O5/c1-4-16-10-18(9-15(2)23(16)32-14-20(30)13-29)24-27-25(33-28-24)19-11-21(17-7-5-6-8-17)26-22(12-19)31-3/h9-12,17,20,29-30H,4-8,13-14H2,1-3H3/t20-/m0/s1
comment: Cenerimod is a potent and selective S1P1 receptor modulator with unique S1P1 receptor signaling properties and absence of broncho- and vasoconstrictor effects ex vivo and in vivo. It dose-dependently lowered circulating lymphocyte counts in rats and mice after oral administration and effectively attenuated disease parameters in a mouse experimental autoimmune encephalitis (EAE) model <Reference id=34394/>. There is an Actelion patent where cenerimod is example 2 along with 30 EC50 values <Reference id=34395/>.
iupac name: (2S)-3-[4-[5-(2-cyclopentyl-6-methoxypyridin-4-yl)-1,2,4-oxadiazol-3-yl]-2-ethyl-6-methylphenoxy]propane-1,2-diol
synonym: ACT-334441
approved: f
ligand name: cenerimod
type: SyntheticOrganicLigand

9-phenanthrol
canonical SMILES: Oc1cc2ccccc2c2c1cccc2
isomeric SMILES: Oc1cc2ccccc2c2c1cccc2
in ch i key: DZKIUEHLEXLYKM-UHFFFAOYSA-N
in ch i: InChI=1S/C14H10O/c15-14-9-10-5-1-2-6-11(10)12-7-3-4-8-13(12)14/h1-9,15H
comment: Inhibitor of TRPM4 <Reference id=24096/>.
iupac name: phenanthren-9-ol
xref: CHEMBL2407182
approved: f
ligand name: 9-phenanthrol
type: SyntheticOrganicLigand

NB-360
in ch i key: BQFHTVUWPJXLOW-VQTJNVASSA-N
in ch i: InChI=1S/C21H19F4N5O2/c1-11-6-12(8-26)9-28-16(11)17(31)29-13-4-5-15(22)14(7-13)19(2)10-32-20(3,18(27)30-19)21(23,24)25/h4-7,9H,10H2,1-3H3,(H2,27,30)(H,29,31)/t19-,20+/m0/s1
comment: Due to good brain penetration, oral doses of Novartis NB-360 completely block amyloid-β deposition in an APP transgenic mouse model <Reference id=34385/>. Data across species suggest similar treatment effects can possibly be achieved in humans. The reduced neuroinflammation upon amyloid reduction by NB-360 treatment supports the notion that targeting amyloid-β pathology can have beneficial downstream effects on the progression of Alzheimer's disease. Note this inhibitor is equipotent against BACE2 in vitro. NB-360 did not progress to clinical development, but is suitable as an effective pharmacological tool to investigate the effects of BACE-1 inhibition in Alzherimer's disease models <Reference id=38241/>. There is a recent paper describing impairment of synaptic plasticity in mice via Seizure Protein 6 <Reference id=34386/>. One of the Novartis patents has a SAR set of 184 IC50 values <Reference id=34392/>.
iupac name: N-[3-[(3R,6R)-5-amino-3,6-dimethyl-6-(trifluoromethyl)-2H-1,4-oxazin-3-yl]-4-fluorophenyl]-5-cyano-3-methylpyridine-2-carboxamide
xref: CHEMBL3261067
synonym: NB360
synonym: NB 360
approved: f
ligand name: NB-360
type: SyntheticOrganicLigand

RO5508887
in ch i key: DVMUZHLUMHPCGZ-QGZVFWFLSA-N
in ch i: InChI=1S/C18H14F3N5O2/c1-17(18(20,21)9-28-16(23)26-17)12-6-11(3-4-13(12)19)25-15(27)14-5-2-10(7-22)8-24-14/h2-6,8H,9H2,1H3,(H2,23,26)(H,25,27)/t17-/m1/s1
comment: Roche progressed RG7129/RO5508887 into clinical trials in 2011 as a potent aminooxazoline inhibitor against BACE1 but not selective over BACE2. In October 2013, development ceased without explanation. The most recent peer reviewed paper, is a mouse study in combination with anti-Aβ antibody gantenerumab <Reference id=34373/>. A patent has published with an SAR set of 84 IC50 values <Reference id=34374/>, and there are also a total of 14 PDB structures from this series published, including RO5508887 <Reference id=23498/>.
iupac name: N-[3-[(4R)-2-amino-5,5-difluoro-4-methyl-6H-1,3-oxazin-4-yl]-4-fluorophenyl]-5-cyanopyridine-2-carboxamide
xref: CHEMBL2347215
synonym: RG7129
approved: f
ligand name: RO5508887
type: SyntheticOrganicLigand

compound 11 [PMID: 29442501]
in ch i key: QFLWZFQWSBQYPS-AWRAUJHKSA-N
comment: Compound 11 is a peptidyl-diphenyl phosphonate PR3 inhibitor, designed for enhanced inhibitory efficacy <Reference id=34329/>. PR3 inhibitors have therapeutic potential for infectious and inflammatory diseases. Its peptide structure is represented as Bt-Val-Tyr-Asp-nValP(O-C6H4-4-Cl)2. Compound 11 is suitable for studies in primate models and human tissues, but is inactive vs. rodent PR3 <Reference id=34329/>.
iupac name: (3S)-3-[(2S)-2-[(2S)-2-{5-[(3aS,6aR)-2-oxo-hexahydro-1H-thieno[3,4-d]imidazolidin-4-yl]pentanamido}-3-methylbutanamido]-3-(4-hydroxyphenyl)propanamido]-3-({1-[bis(4-chlorophenoxy)phosphoryl]butyl}carbamoyl)propanoic acid
approved: f
ligand name: compound 11 [PMID: 29442501]
type: SyntheticOrganicLigand

elenbecestat
in ch i key: AACUJFVOHGRMTR-DPXNYUHVSA-N
comment: BACE1 inhibitor for Alzheimer's disease jointly developed by Eisai and Biogen Inc. Phase 3 clinical study and FDA granted Fast Track designation. As of Feb 2018 no peer reviewed journal publications but structure identified in the patent <Reference id=34301/>.
iupac name: N-[3-[(4aS,5R,7aS)-2-amino-5-methyl-4,4a,5,7-tetrahydrofuro[3,4-d][1,3]thiazin-7a-yl]-4-fluorophenyl]-5-(difluoromethyl)pyrazine-2-carboxamide
synonym: E-2609
synonym: E2609
synonym: E 2609
approved: f
ligand name: elenbecestat
type: SyntheticOrganicLigand

Yoda1
canonical SMILES: Clc1cccc(c1CSc1nnc(s1)c1cnccn1)Cl
isomeric SMILES: Clc1cccc(c1CSc1nnc(s1)c1cnccn1)Cl
in ch i key: BQNXBSYSQXSXPT-UHFFFAOYSA-N
in ch i: InChI=1S/C13H8Cl2N4S2/c14-9-2-1-3-10(15)8(9)7-20-13-19-18-12(21-13)11-6-16-4-5-17-11/h1-6H,7H2
comment: Piezo1 channel activator
iupac name: 2-[5-[(2,6-dichlorophenyl)methylsulfanyl]-1,3,4-thiadiazol-2-yl]pyrazine
synonym: Yoda 1
approved: f
ligand name: Yoda1
type: SyntheticOrganicLigand

CCT196969
in ch i key: KYYKGSDLXXKQCR-UHFFFAOYSA-N
in ch i: InChI=1S/C27H24FN7O3/c1-27(2,3)21-14-22(35(34-21)16-7-5-4-6-8-16)32-26(37)31-19-10-9-17(13-18(19)28)38-20-11-12-29-25-24(20)30-15-23(36)33-25/h4-15H,1-3H3,(H,29,33,36)(H2,31,32,37)
comment: CCT196969 is an orally active pan RAF inhibitor that also inhibits SRC family kinases <Reference id=34294/>. It was designed to show that the addition of SRC family kinase inhibition alongside RAF inhibition is able to circumvent the paradoxical SRC-mediated re-activation of the RAF-MAP kinase pathway that is observed in tumours with acquired resistance to RAF inhibitors.
iupac name: 1-(5-tert-butyl-2-phenylpyrazol-3-yl)-3-[2-fluoro-4-[(3-oxo-4H-pyrido[2,3-b]pyrazin-8-yl)oxy]phenyl]urea
approved: f
ligand name: CCT196969
type: SyntheticOrganicLigand

CCT241161
in ch i key: DPMYVVGAYAPQNS-UHFFFAOYSA-N
in ch i: InChI=1S/C28H27N7O3S/c1-28(2,3)22-15-23(35(34-22)17-8-6-5-7-9-17)32-27(37)31-19-11-10-18(14-21(19)39-4)38-20-12-13-29-26-25(20)30-16-24(36)33-26/h5-16H,1-4H3,(H,29,33,36)(H2,31,32,37)
comment: CCT241161 is an orally active pan RAF inhibitor that also inhibits SRC family kinases <Reference id=34294/>. It was designed to show that the addition of SRC family kinase inhibition alongside RAF inhibition is able to circumvent the paradoxical SRC-mediated re-activation of the RAF-MAP kinase pathway that is observed in tumours with acquired resistance to RAF inhibitors. CCT241161 is marginally more potent in vitro than the analogue <Ligand id=9815/> <Reference id=34294/>.
iupac name: 1-(5-tert-butyl-2-phenylpyrazol-3-yl)-3-[2-methylsulfanyl-4-[(3-oxo-4H-pyrido[2,3-b]pyrazin-8-yl)oxy]phenyl]urea
approved: f
ligand name: CCT241161
type: SyntheticOrganicLigand

LUF5962
in ch i key: NDJOQVVSPLVIDN-UHFFFAOYSA-N
in ch i: InChI=1S/C22H20N4/c1-3-9-15(10-4-1)18-19-22(26-21(24-19)17-13-7-8-14-17)25-20(23-18)16-11-5-2-6-12-16/h1-6,9-12,17H,7-8,13-14H2,(H,23,24,25,26)
comment: A1 adenosine receptor antagonist
iupac name: 8-cyclopentyl-2,6-diphenyl-7H-purine
xref: CHEMBL207824
synonym: LUF 5962
synonym: LUF-5962
approved: f
ligand name: LUF5962
type: SyntheticOrganicLigand

AZD9567
in ch i key: ZQFNDBISEYQVRR-LOSJGSFVSA-N
in ch i: InChI=1S/C27H28F2N4O3/c1-17(2)24(31-26(35)27(3,28)29)25(18-8-6-5-7-9-18)36-21-11-12-22-19(14-21)15-30-33(22)20-10-13-23(34)32(4)16-20/h5-17,24-25H,1-4H3,(H,31,35)/t24-,25+/m0/s1
comment: AZD9567 is a synthetic, selective glucocorticoid receptor (GR) partial agonist <Reference id=34289/>. It was designed to offer an improved side-effect profile compared to conventional full agonist GR anti-inflammatory dugs. AZD9567 is one of the chemical structures claimed in patent WO2016046260A1 <Reference id=34290/>.
iupac name: 2,2-difluoro-N-[(1R,2S)-3-methyl-1-[1-(1-methyl-6-oxopyridin-3-yl)indazol-5-yl]oxy-1-phenylbutan-2-yl]propanamide
synonym: compound 15 [PMID: 29424542]
synonym: example 1 [WO2016046260A1]
synonym: AZD-9567
synonym: AZD 9567
approved: f
ligand name: AZD9567
type: SyntheticOrganicLigand

GSK-3β inhibitor 3 [PMID: 25845281]
canonical SMILES: COc1nc(sc1C(=O)N)c1ccnc(c1)NC(=O)C1CC1
isomeric SMILES: COc1nc(sc1C(=O)N)c1ccnc(c1)NC(=O)C1CC1
in ch i key: CYADPSMQNARVII-UHFFFAOYSA-N
in ch i: InChI=1S/C14H14N4O3S/c1-21-13-10(11(15)19)22-14(18-13)8-4-5-16-9(6-8)17-12(20)7-2-3-7/h4-7H,2-3H2,1H3,(H2,15,19)(H,16,17,20)
comment: This compound is a selective GSK-3β inhibitor that was initially discovered in <Reference id=34285/> and subsequently included as one of the active moeities in the novel dual GSK-3β/acetylcholinesterase inhibitor <Ligand id=9810/> <Reference id=34284/>.
iupac name: 2-[2-(cyclopropanecarbonylamino)pyridin-4-yl]-4-methoxy-1,3-thiazole-5-carboxamide
xref: CHEMBL3410089
synonym: GSK-3β inhibitor 1 [Jiang et al., 2018]
approved: f
ligand name: GSK-3β inhibitor 3 [PMID: 25845281]
type: SyntheticOrganicLigand

compound 2f [Jiang et al., 2018]
in ch i key: XYSJVXMQSXKJCN-UHFFFAOYSA-N
in ch i: InChI=1S/C30H32N6O3S/c1-39-29-26(40-30(36-29)19-13-16-31-24(17-19)35-27(37)18-11-12-18)28(38)33-15-6-14-32-25-20-7-2-4-9-22(20)34-23-10-5-3-8-21(23)25/h2,4,7,9,13,16-18H,3,5-6,8,10-12,14-15H2,1H3,(H,32,34)(H,33,38)(H,31,35,37)
comment: Compound 2f is a hybrid molecule that combines a selective glycogen synthase kinase-3β (GSK-3β) inhibitor (<Ligand id=9811/>) with the acetylcholinesterase (AChE) inhibitor <Ligand id=6687/> <Reference id=34284/>. It is predicted that this approach may improve clinical efficacy in Alzheimer's disease (AD) by simultaneously targeting these two crucial AD targets, and presents as a useful tool for furthering AD drug discovery. It is active in vitro and in vivo.
iupac name: 2-(2-cyclopropaneamidopyridin-4-yl)-4-methoxy-N-{3-[(1,2,3,4-tetrahydroacridin-9-yl)amino]propyl}-1,3-thiazole-5-carboxamide
synonym: dual GSK-3β/AChE inhibitor
approved: f
ligand name: compound 2f [Jiang et al., 2018]
type: SyntheticOrganicLigand

derivative 17 [Nakahata et al., 2018]
in ch i key: VJMRKWPMFQGIPI-UHFFFAOYSA-N
comment: Derivative 17 is a potent GPR52 agonist with in vivo activity <Reference id=34226/>. GPR52 agonists are being investigated as novel anti-psychotics.
iupac name: N-(2-hydroxyethyl)-5-(hydroxymethyl)-3-methyl-1-[2-[[3-(trifluoromethyl)phenyl]methyl]-1-benzothiophen-7-yl]pyrazole-4-carboxamide
synonym: example 65 [WO2011078360]
approved: f
ligand name: derivative 17 [Nakahata et al., 2018]
type: SyntheticOrganicLigand

seletalisib
in ch i key: LNLJHGXOFYUARS-OAQYLSRUSA-N
comment: Seletalisib is an orally bioavailable, potent and selective, ATP-competitive, small molecule inhibitor of PI3Kδ that is being developed by UCB Pharma for the treatment of immune and inflammatory diseases <Reference id=34209/>.
iupac name: 3-{8-chloro-3-[(1R)-2,2,2-trifluoro-1-({pyrido[3,2-d]pyrimidin-4-yl}amino)ethyl]quinolin-2-yl}pyridin-1-ium-1-olate
synonym: UCB 5857
synonym: UCB-5857
synonym: UCB5857
approved: f
ligand name: seletalisib
type: SyntheticOrganicLigand

Sch.336
in ch i key: NXODIUKWAVUFGF-INIZCTEOSA-N
in ch i: InChI=1S/C23H25NO8S3/c1-16(24-33(4,25)26)17-5-10-20(11-6-17)34(27,28)22-14-9-19(32-3)15-23(22)35(29,30)21-12-7-18(31-2)8-13-21/h5-16,24H,1-4H3/t16-/m0/s1
comment: Sch.336 is a novel inverse agonist that is selective for the cannabinoid receptor CB2 that is expressed on peripheral immune cells <Reference id=34206/><Reference id=34205/>. It is suitable for in vitro and in vivo studies.
xref: CHEMBL180465
synonym: SCH336
synonym: SCH-336
synonym: analog 4j [PMID: 15664857]
approved: f
ligand name: Sch.336
type: SyntheticOrganicLigand

darigabat
in ch i key: PTTQXDBPTFOCMT-UHFFFAOYSA-N
in ch i: InChI=1S/C22H21FN4O3S/c1-4-27-13-24-21-18(12-25-26-22(21)27)14-6-9-19(23)17(10-14)16-8-7-15(11-20(16)30-3)31(28,29)5-2/h6-13H,4-5H2,1-3H3
comment: Darigabat (PF-06372865) is an orally active, GABAA receptor positive allosteric modulator, that selectively targets GABAA receptors containing α2/3/5 subunits over receptors containing α1 subunits <Reference id=34203/><Reference id=38736/>. The α1 subunit is associated with the (undesirable) sedative effects of benzodiazepine drugs, whilst the α2/3 subunits contribute to their anxiolytic and analgesic activities and the α5 subunit to effects on memory function. The chemical structure of this compound is claimed as 'Example 4' in patent WO2014091368 <Reference id=34204/>. Pfizer are developing PF-06372865 for clinical potential in the treatment of chronic pain <Reference id=37542/> and photosensitive epilepsy, but have terminated development in generalized anxiety disorder.
iupac name: 7-ethyl-4-[3-(4-ethylsulfonyl-2-methoxyphenyl)-4-fluorophenyl]imidazo[4,5-c]pyridazine
xref: CHEMBL3647536
synonym: example 4 [WO2014091368]
synonym: PF06372865
synonym: PF 06372865
synonym: PF-06372865
approved: f
ligand name: darigabat
type: SyntheticOrganicLigand

compound 37 [PMID: 29193967]
in ch i key: GADGQEKPNKSGMT-UHFFFAOYSA-N
comment: Compound 37 [PMID: 29193967] is a potent, orally bioavailable PLA2-G7 (Lp-PLA2) inhibitor. Structurally it is has a novel sulfonamide scaffold, and is a candidate for further optimisation. Compounds of different chemotypes are being explored as tools to examine the pharmacological modulation of PLA2-G7 as a target for clinical intervention- see also <Ligand id=6696/> (failed Phase 3 trial in coronary heart disease), <Ligand id=7376/> (completed Phase 2 for Alzheimer's disease) and <Ligand id=9796/> (tool compound).
approved: f
ligand name: compound 37 [PMID: 29193967]
type: SyntheticOrganicLigand

(S)-23 [PMID: 27933945]
in ch i key: SYEMWCXBADSSGE-OAHLLOKOSA-N
in ch i: InChI=1S/C19H23FN2O4S/c1-19(4-8-27(24,25)9-5-19)15-11-18(23)22(13-15)6-7-26-16-2-3-17(20)14(10-16)12-21/h2-3,10,15H,4-9,11,13H2,1H3/t15-/m1/s1
comment: Compound (S)-23 is a γ-lactam sulfone type PLA2-G7 (Lp-PLA2) inhibitor <Reference id=34194/>. It is less lipophilic than the clinically evaluated inhibitor, <Ligand id=6696/>.
iupac name: 2-fluoro-5-[2-[(4S)-4-(4-methyl-1,1-dioxothian-4-yl)-2-oxopyrrolidin-1-yl]ethoxy]benzonitrile
approved: f
ligand name: (S)-23 [PMID: 27933945]
type: SyntheticOrganicLigand

CU-CPT8m
canonical SMILES: Cc1cccc(c1)c1ccnc2n1ncc2C(=O)N
isomeric SMILES: Cc1cccc(c1)c1ccnc2n1ncc2C(=O)N
in ch i key: HNKGGVGQAVODNJ-UHFFFAOYSA-N
in ch i: InChI=1S/C14H12N4O/c1-9-3-2-4-10(7-9)12-5-6-16-14-11(13(15)19)8-17-18(12)14/h2-8H,1H3,(H2,15,19)
comment: CU-CPT8m is a small molecule functional Toll-like receptor 8 (TLR8) inhibitor <Reference id=34190/>. Analysis reveals that the compound binds to a site between the two subunits of the TLR8 homodimer, in its resting state, and so prevents activation.
iupac name: 7-(3-methylphenyl)pyrazolo[1,5-a]pyrimidine-3-carboxamide
synonym: compound 5 [PMID: 29155428]
synonym: 7-(m-Tolyl)pyrazolo[1,5-a]pyrimidine-3-carboxamide
approved: f
ligand name: CU-CPT8m
type: SyntheticOrganicLigand

enexasogaol
canonical SMILES: CCCCCC=CC(=O)CCc1ccc(c(c1)OC)O
isomeric SMILES: CCCCC/C=C/C(=O)CCc1ccc(c(c1)OC)O
in ch i key: OQWKEEOHDMUXEO-BQYQJAHWSA-N
in ch i: InChI=1S/C17H24O3/c1-3-4-5-6-7-8-15(18)11-9-14-10-12-16(19)17(13-14)20-2/h7-8,10,12-13,19H,3-6,9,11H2,1-2H3/b8-7+
comment: Enexasogaol (6-Shogaol) is a bioactive phytochemical isolated from ginger (Zingiber officinale Roscoe). It has anti-inflammatory, analgesic and antioxidant properties <Reference id=34104/><Reference id=34103/><Reference id=34105/><Reference id=34106/>.
iupac name: (E)-1-(4-hydroxy-3-methoxyphenyl)dec-4-en-3-one
xref: CHEMBL25948
synonym: trans-6-shogaol
synonym: [6]-shogaol
synonym: 6-Shogaol
approved: f
ligand name: enexasogaol
type: SyntheticOrganicLigand

compound 7f [PMID: 29191554]
isomeric SMILES: CC[C@H](c1ccc(c(c1)N)C(=O)O)NC(=O)N1C/C(=N/Oc2ccccc2)/NC[C@H](C1=O)Cc1cc(Cl)ccc1OC
in ch i key: LHASZEBEQGPCFM-CJFMBICVSA-N
in ch i: InChI=1S/C30H32ClN5O6/c1-3-25(18-9-11-23(29(38)39)24(32)15-18)34-30(40)36-17-27(35-42-22-7-5-4-6-8-22)33-16-20(28(36)37)13-19-14-21(31)10-12-26(19)41-2/h4-12,14-15,20,25H,3,13,16-17,32H2,1-2H3,(H,33,35)(H,34,40)(H,38,39)/t20-,25-/m1/s1
comment: Compound 7f [PMID: 29191554] is a chymase 1 inhbitor <Reference id=34186/>. The chemical structure is claimed as example/compound 32 in patent WO2011078413 <Reference id=34187/>.
iupac name: 2-amino-4-[(1R)-1-{[(3Z,6R)-6-[(5-chloro-2-methoxyphenyl)methyl]-7-oxo-3-(phenoxyimino)-1,4-diazepane-1-carbonyl]amino}propyl]benzoic acid
synonym: example 32 [WO2011078413]
approved: f
ligand name: compound 7f [PMID: 29191554]
type: SyntheticOrganicLigand

vamotinib
in ch i key: SLIVDYMORZGPLW-UHFFFAOYSA-N
in ch i: InChI=1S/C29H27F3N6O/c1-20-6-7-22(17-21(20)9-11-27-35-34-26-5-3-4-12-38(26)27)28(39)33-24-10-8-23(25(18-24)29(30,31)32)19-37-15-13-36(2)14-16-37/h3-8,10,12,17-18H,13-16,19H2,1-2H3,(H,33,39)
comment: Vamotinib (PF-114) is a third generation BCR-ABL kinase inhibitor <Reference id=34178/><Reference id=34180/>. It was designed to target wild-type resistance mutations in BCR-ABL (including the T315I gatekeeper mutation) in order to overcome drug resistance in Philadelphia chromosome positive (Ph+) leukemias. The chemical strucure is claimed in patent WO2012173521 where it is the first compound listed in Table 1 of the patent <Reference id=34179/>. Off-targets identified by kinase profile screening include ABL2/ARG, DDR1, DDR2, FMS, FRK/PTK5, LCK, LYN, LYNB, PDGFRα and RET which had <10% residual activity when exposed to 100 nM of inhibitor <Reference id=34178/>. We matched PF-114's chemical structure to the INN 'vamotinib' that was released in the WHO's proposed INN list 127 (21 July 2022).
iupac name: 4-methyl-N-{4-[(4-methylpiperazin-1-yl)methyl]-3-(trifluoromethyl)phenyl}-3-(2-{[1,2,4]triazolo[4,3-a]pyridin-3-yl}ethynyl)benzamide
xref: CHEMBL4297478
synonym: compound 1 (Table 1) [WO2012173521]
synonym: PF114
synonym: PF 114
synonym: PF-114
approved: f
ligand name: vamotinib
type: SyntheticOrganicLigand

BI-2545
in ch i key: ZDOBSAPHUUUOHX-BJWYYQGGSA-N
in ch i: InChI=1S/C23H19F6N5O3/c24-22(25,26)13-3-11(4-14(6-13)23(27,28)29)10-37-21(36)34-8-16-15(17(16)9-34)7-30-20(35)12-1-2-18-19(5-12)32-33-31-18/h1-6,15-17H,7-10H2,(H,30,35)(H,31,32,33)/t15-,16+,17-
comment: BI-2545 is a potent autotaxin inhibitor <Reference id=34173/>, that is a tool compound suitable for in vitro and in vivo studies. It is one of the compounds available via the Boehringer Ingelheim opnMe innovation/collaboration molecular library. Click here to link to the opnMe page for BI-2545.
iupac name: [3,5-bis(trifluoromethyl)phenyl]methyl (1R,5S,6S)-6-{[(1H-1,2,3-benzotriazol-5-yl)formamido]methyl}-3-azabicyclo[3.1.0]hexane-3-carboxylate
synonym: BI2545
synonym: BI 2545
synonym: compound 19 [PMID: 29259743]
approved: f
ligand name: BI-2545
type: SyntheticOrganicLigand

PIM447
in ch i key: VRQXRVAKPDCRCI-ZNMIVQPWSA-N
in ch i: InChI=1S/C24H23F3N4O/c1-13-9-14(11-15(28)10-13)16-7-8-29-12-21(16)31-24(32)20-6-5-19(27)23(30-20)22-17(25)3-2-4-18(22)26/h2-8,12-15H,9-11,28H2,1H3,(H,31,32)/t13-,14+,15-/m0/s1
comment: PIM447 is a potent and selective pan PIM kinase inhibitor <Reference id=34170/>, that is being investigated for clinical efficacy against hematological malignancies.
iupac name: N-[4-[(1R,3S,5S)-3-amino-5-methylcyclohexyl]pyridin-3-yl]-6-(2,6-difluorophenyl)-5-fluoropyridine-2-carboxamide
xref: CHEMBL3651966
synonym: LGH-447
synonym: LGH447
synonym: PIM-447
synonym: PIM 447
synonym: compound 8 [PMID: 26505898]
approved: f
ligand name: PIM447
type: SyntheticOrganicLigand

rogaratinib
in ch i key: HNLRRJSKGXOYNO-UHFFFAOYSA-N
in ch i: InChI=1S/C23H26N6O3S/c1-13-6-14-8-18(33-22(14)17(7-13)32-3)20-15(11-31-2)16(9-28-5-4-25-19(30)10-28)29-21(20)23(24)26-12-27-29/h6-8,12H,4-5,9-11H2,1-3H3,(H,25,30)(H2,24,26,27)
comment: Rogaratinib (BAY-1163877) is a FGFR-selective kinase inhibitor that is being investigated for antineoplastic activity. The parent molecular structure is claimed as Example 1 in patent WO2013087578, and the dihydrochloride is claimed as Example 2 <Reference id=34168/>.
iupac name: 4-[[4-amino-6-(methoxymethyl)-5-(7-methoxy-5-methyl-1-benzothiophen-2-yl)pyrrolo[2,1-f][1,2,4]triazin-7-yl]methyl]piperazin-2-one
synonym: BAY-1163877
synonym: BAY1163877
synonym: Example 1 [WO2013087578]
approved: f
ligand name: rogaratinib
type: SyntheticOrganicLigand

PRN1371
in ch i key: PUIXMSRTTHLNKI-UHFFFAOYSA-N
comment: PRN1371 is an irreversible (covalent) and potent FGFR inhibitor that is being developed for antineoplastic potential <Reference id=34167/>. It is highly selective for FGFR1-4 compared to other kinase enzymes.
iupac name: 6-(2,6-dichloro-3,5-dimethoxyphenyl)-2-(methylamino)-8-[3-(4-prop-2-enoylpiperazin-1-yl)propyl]pyrido[2,3-d]pyrimidin-7-one
synonym: compound 34 [PMID: 28665128]
synonym: PRN-1371
synonym: PRN 1371
approved: f
ligand name: PRN1371
type: SyntheticOrganicLigand

zoligratinib
in ch i key: BEMNJULZEQTDJY-UHFFFAOYSA-N
in ch i: InChI=1S/C20H16N6O/c1-11-23-16-7-6-13(9-17(16)24-11)26-20(21)14(10-22-26)19(27)18-8-12-4-2-3-5-15(12)25-18/h2-10,25H,21H2,1H3,(H,23,24)
comment: Zoligratinib (DEBIO1347) is a FGFR1/2/3 inhibitor that is being investigated for antineoplastic activity <Reference id=34166/>. The compound is ATP-competitive, potent and orally available.
iupac name: [5-amino-1-(2-methyl-3H-benzimidazol-5-yl)pyrazol-4-yl]-(1H-indol-2-yl)methanone
synonym: DEBIO-1347
synonym: CH5183284
synonym: DEBIO1347
approved: f
ligand name: zoligratinib
type: SyntheticOrganicLigand

futibatinib
canonical SMILES: C=CC(=O)N1CCC(C1)n1nc(c2c1ncnc2N)C#Cc1cc(OC)cc(c1)OC
isomeric SMILES: C=CC(=O)N1CC[C@@H](C1)n1nc(c2c1ncnc2N)C#Cc1cc(OC)cc(c1)OC
in ch i key: KEIPNCCJPRMIAX-HNNXBMFYSA-N
in ch i: InChI=1S/C22H22N6O3/c1-4-19(29)27-8-7-15(12-27)28-22-20(21(23)24-13-25-22)18(26-28)6-5-14-9-16(30-2)11-17(10-14)31-3/h4,9-11,13,15H,1,7-8,12H2,2-3H3,(H2,23,24,25)/t15-/m0/s1
comment: Futibatinib (TAS-120) is a covalent (irreversible), non-selective FGFR inhibitor that was developed for anti-tumour activity <Reference id=44195/>. It is claimed as Example 2 in patent WO2013108809 <Reference id=34165/>. It can overcome acquired resistance to ATP-competitive FGFR inhibitors (such as <Ligand id=7877/> and <Ligand id=9787/>) in intrahepatic cholangiocarcinomas that harbour FGFR2 kinase domain mutations <Reference id=44193/>. A case study in a patient with metastatic cholangiocarcinoma, whose tumour had a FGFR2-CORO2B gene fusion and a <Ligand id=9767/>-induced resistance mutation, demonstrated tumour shrinkage in response to futibatinib treatment <Reference id=44196/>.
iupac name: 1-[(3S)-3-[4-amino-3-[2-(3,5-dimethoxyphenyl)ethynyl]pyrazolo[3,4-d]pyrimidin-1-yl]pyrrolidin-1-yl]prop-2-en-1-one
xref: CHEMBL3701238
synonym: TAS120
synonym: TAS 120
synonym: Example 2 [WO2013108809]
synonym: FGFR-IN-1
synonym: TAS-120
synonym: Lytgobi®
approved: t
ligand name: futibatinib
type: SyntheticOrganicLigand

derazantinib
in ch i key: KPJDVVCDVBFRMU-AREMUKBSSA-N
in ch i: InChI=1S/C29H29FN4O/c1-35-16-15-31-14-13-20-7-6-8-22(17-20)33-29-32-19-21-18-26(24-10-4-5-12-27(24)30)23-9-2-3-11-25(23)28(21)34-29/h2-12,17,19,26,31H,13-16,18H2,1H3,(H,32,33,34)/t26-/m1/s1
comment: Derazantinib (ARQ087) is an orally bioavailable, non-selective FGFR inhibitor being investigated for antineoplastic activity. Preclinical activity is reported by Hall et al. (2016) <Reference id=34163/>.
iupac name: (6R)-6-(2-fluorophenyl)-N-[3-[2-(2-methoxyethylamino)ethyl]phenyl]-5,6-dihydrobenzo[h]quinazolin-2-amine
synonym: ARQ087
synonym: ARQ-087
synonym: ARQ 087
approved: f
ligand name: derazantinib
type: SyntheticOrganicLigand

compound 7f [PMID: 29283260]
in ch i key: BADSWYIEDNZIEB-UHFFFAOYSA-N
in ch i: InChI=1S/C19H29ClN6/c1-14(2)13-26(10-7-15-3-5-16(20)6-4-15)17-8-11-25(12-9-17)19-22-18(21)23-24-19/h3-6,14,17H,7-13H2,1-2H3,(H3,21,22,23,24)
comment: Compound 7f is an orally bioavailable acidic mammalian chitinase (AMCase; CHIA) inhibitor <Reference id=34150/>.
iupac name: 1-(3-amino-1H-1,2,4-triazol-5-yl)-N-[2-(4-chlorophenyl)ethyl]-N-(2-methylpropyl)piperidin-4-amine
approved: f
ligand name: compound 7f [PMID: 29283260]
type: SyntheticOrganicLigand

TY-51469
in ch i key: CBRCULCCRGSSLB-UHFFFAOYSA-N
comment: TY-51469 is a chymase inhibitor <Reference id=34145/>.
iupac name: 2-[4-[(5-fluoro-3-methyl-1-benzothiophen-2-yl)sulfonylamino]-3-methylsulfonylphenyl]-1,3-thiazole-4-carboxylic acid
approved: f
ligand name: TY-51469
type: SyntheticOrganicLigand

difamilast
in ch i key: VFBILHPIHUPBPZ-UHFFFAOYSA-N
in ch i: InChI=1S/C23H24F2N2O5/c1-4-29-18-8-6-5-7-17(18)21(28)26-12-16-13-30-22(27-16)15-9-10-19(32-23(24)25)20(11-15)31-14(2)3/h5-11,13-14,23H,4,12H2,1-3H3,(H,26,28)
comment: Difamilast (OPA-15406) is a topical, selective, nonsteroidal PDE4 inhibitor that is being developed for the treatment of atopic dermatitis <Reference id=34113/>. The chemical structure is claimed as example 352 in patent WO2007058338 <Reference id=34115/>.
iupac name: N-[[2-[4-(difluoromethoxy)-3-propan-2-yloxyphenyl]-1,3-oxazol-4-yl]methyl]-2-ethoxybenzamide
synonym: MM36
synonym: example 352 [WO2007058338]
synonym: OPA-15406
approved: f
ligand name: difamilast
type: SyntheticOrganicLigand

diroleuton
canonical SMILES: CCCCCC=CCC=CCC=CCCCCCCC(=O)O
isomeric SMILES: CCCCC/C=C/C/C=C/C/C=C/CCCCCCC(=O)O
in ch i key: HOBAELRKJCKHQD-QNEBEIHSSA-N
in ch i: InChI=1S/C20H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h6-7,9-10,12-13H,2-5,8,11,14-19H2,1H3,(H,21,22)/b7-6-,10-9-,13-12-
comment: Diroleuton (dihomo-gamma-linolenic acid; DGLA) is a 20-carbon-chain fatty acid that is structurally very similar to arachadonic acid (AA). It competes with AA for binding to the substrate binding sites of the COX and lipoxygenase enzymes, and this effect reduces the production of inflammatory mediators (eicosanoids) from AA. DGLA can be converted to <Ligand id=1882/> and eicosapentaenoic acid (<Ligand id=3362/>), the latter being a precursor for the synthesis of series-3 prostaglandins, series-5 leukotrienes and series-3 thromboxanes.
iupac name: (8Z,11Z,14Z)-icosa-8,11,14-trienoic acid
xref: CHEMBL465183
synonym: DGLA
synonym: 8,11,14-Eicosatrienoic acid
synonym: Homo-gamma-linolenic acid
synonym: DS107
synonym: dihomo-gamma-linolenic acid
approved: f
ligand name: diroleuton
type: SyntheticOrganicLigand

elismetrep
in ch i key: CWEFDWIKLABKBX-UHFFFAOYSA-N
comment: Elismetrep (example 104) is claimed in patent WO2012124825 as a TRPM8 antagonist <Reference id=34108/>. TRPM8 antagonists have been considered as non-opioid analgesics for the treatment of chronic pain, or as agents to combat cold induced allodynia and hyperalgesia (reviewed in <Reference id=34109/>). TRPM8 antagonists can cause an adverse effect of hot sensation or induce hypothermia.
iupac name: 4-[(4-cyclopropylisoquinolin-3-yl)-[[4-(trifluoromethoxy)phenyl]methyl]sulfamoyl]benzoic acid
xref: CHEMBL3682589
synonym: example 104 [WO2012124825]
approved: f
ligand name: elismetrep
type: SyntheticOrganicLigand

(S)-chlorosuccinic acid
canonical SMILES: OC(=O)CC(C(=O)O)Cl
isomeric SMILES: OC(=O)C[C@@H](C(=O)O)Cl
in ch i key: QEGKXSHUKXMDRW-REOHCLBHSA-N
in ch i: InChI=1S/C4H5ClO4/c5-2(4(8)9)1-3(6)7/h2H,1H2,(H,6,7)(H,8,9)/t2-/m0/s1
comment: Succinate receptor agonist
iupac name: (2S)-2-chlorobutanedioic acid
synonym: (S)-2-chlorosuccinic acid
approved: f
ligand name: (S)-chlorosuccinic acid
type: SyntheticOrganicLigand

lenabasum
in ch i key: YCHYFHOSGQABSW-RTBURBONSA-N
in ch i: InChI=1S/C25H36O4/c1-6-7-8-9-12-24(2,3)17-14-20(26)22-18-13-16(23(27)28)10-11-19(18)25(4,5)29-21(22)15-17/h10,14-15,18-19,26H,6-9,11-13H2,1-5H3,(H,27,28)/t18-,19-/m1/s1
comment: Lenabasum (ajulemic acid) is a synthetic derivative of the non-psychoactive cannabinoid THC metabolite 11-nor-9-Carboxy-THC (PubChem CID 108207) <Reference id=34099/>. It is a non-selective cannabinoid receptor agonist <Reference id=34096/><Reference id=34097/>. Lenabasum exhibits potentially useful analgesic and anti-inflammatory actions <Reference id=34098/>.
iupac name: (6aR,10aR)-1-hydroxy-6,6-dimethyl-3-(2-methyloctan-2-yl)-6a,7,10,10a-tetrahydrobenzo[c]chromene-9-carboxylic acid
xref: CHEMBL456341
synonym: CPL-7075
synonym: CPL7075
synonym: IP751
synonym: IP-751
synonym: CT-3
synonym: ajulemic acid
approved: f
ligand name: lenabasum
type: SyntheticOrganicLigand

mosedipimod
in ch i key: GAKUNXBDVGLOFS-UHFFFAOYSA-N
in ch i: InChI=1S/C39H70O6/c1-4-6-8-10-12-14-16-18-19-21-23-25-27-29-31-33-39(42)45-37(34-43-36(3)40)35-44-38(41)32-30-28-26-24-22-20-17-15-13-11-9-7-5-2/h12,14,18-19,37H,4-11,13,15-17,20-35H2,1-3H3
comment: Mosedipimod (EC-18) is a monoacetyldiglyceride that is being investigated for anti-inflammatory potential <Reference id=34094/>. It is a synthetic form of a major constituent isolated from the antlers of Sika deer. In preclinical studies the anti-inflammatory effects were determined to be associated with iNOS suppression <Reference id=34091/>. EC-18 has also been shown to attenuate IL-4 production <Reference id=34093/>. We show the chemical structure without specified stereochemisrty to represent the racemic mixture. Note that CHEMBL157366 represents a specific stereoisomer of this compound.
iupac name: (1-acetyloxy-3-hexadecanoyloxypropan-2-yl) (9Z,12Z)-octadeca-9,12-dienoate
synonym: Plag, (+/-)
synonym: EC-18
approved: f
ligand name: mosedipimod
type: SyntheticOrganicLigand

tepilamide fumarate
canonical SMILES: CCN(C(=O)COC(=O)C=CC(=O)OC)CC
isomeric SMILES: CCN(C(=O)COC(=O)/C=C/C(=O)OC)CC
in ch i key: AKUGRXRLHCCENI-VOTSOKGWSA-N
in ch i: InChI=1S/C11H17NO5/c1-4-12(5-2)9(13)8-17-11(15)7-6-10(14)16-3/h6-7H,4-5,8H2,1-3H3/b7-6+
comment: Tepilamide fumarate (XP23829) is a small-molecule fumaric acid ester prodrug of <Ligand id=5786/> (MMF). It is being developed by Arbor Pharmaceuticals (formerly XenoPort) as a potential treatment for autoinflammatory diseases.
iupac name: 4-O-[2-(diethylamino)-2-oxoethyl] 1-O-methyl (E)-but-2-enedioate
synonym: XP-23829
synonym: XP 23829
synonym: XP23829
approved: f
ligand name: tepilamide fumarate
type: SyntheticOrganicLigand

surufatinib
in ch i key: TTZSNFLLYPYKIL-UHFFFAOYSA-N
in ch i: InChI=1S/C24H28N6O3S/c1-17-13-19-15-21(7-8-22(19)27-17)33-23-9-10-25-24(29-23)28-20-6-4-5-18(14-20)16-34(31,32)26-11-12-30(2)3/h4-10,13-15,26-27H,11-12,16H2,1-3H3,(H,25,28,29)
comment: Surufatinib is an oral tyrosine kinase inhibitor that selectively targets VEGFR 1, 2, and 3, FGFR1 and CSF-1R, to inhibit key angiogenic and immune pathways in solid tumours. Surufatinib's chemical structure is claimed in patent WO2011060746, and its use as a potential anti-angiogenic agent is included <Reference id=34087/>. In this patent it is referred to as 'Compound of Formula A'.
iupac name: N-[2-(dimethylamino)ethyl]-1-[3-[[4-[(2-methyl-1H-indol-5-yl)oxy]pyrimidin-2-yl]amino]phenyl]methanesulfonamide
synonym: KDR-IN-1
synonym: VEGFR2 inhibitor [WO2011060746]
synonym: HMPL-012
synonym: HMPL012
synonym: Sulanda®
approved: t
ligand name: surufatinib
type: SyntheticOrganicLigand

roblitinib
in ch i key: BHKDKKZMPODMIQ-UHFFFAOYSA-N
in ch i: InChI=1S/C25H30N8O4/c1-31-7-8-32(23(35)15-31)14-18-10-17-4-3-6-33(24(17)29-21(18)16-34)25(36)30-22-11-20(27-5-9-37-2)19(12-26)13-28-22/h10-11,13,16H,3-9,14-15H2,1-2H3,(H2,27,28,30,36)
comment: Roblitinib (FGF401) is a first-in-class, potent and selective, reversible-covalent FGFR4 inhibitor. It is claimed as example 83 in patent US9266883 <Reference id=34086/>. FGF401 is being evaluated for antineoplastic effects against solid tumours characterized by FGFR4, FGF19 or KLB/Klothoβ expression, in particular for FGF19-driven hepatocellular carcinoma <Reference id=38167/>.
iupac name: N-[5-cyano-4-(2-methoxyethylamino)pyridin-2-yl]-7-formyl-6-[(4-methyl-2-oxopiperazin-1-yl)methyl]-3,4-dihydro-2H-1,8-naphthyridine-1-carboxamide
synonym: FGF-401
synonym: Example 83 [US9266883]
synonym: NVP-FGF401
synonym: FGF401
approved: f
ligand name: roblitinib
type: SyntheticOrganicLigand

pemigatinib
in ch i key: HCDMJFOHIXMBOV-UHFFFAOYSA-N
in ch i: InChI=1S/C24H27F2N5O4/c1-4-30-21-14(11-27-23-16(21)9-15(28-23)13-29-5-7-35-8-6-29)12-31(24(30)32)22-19(25)17(33-2)10-18(34-3)20(22)26/h9-11H,4-8,12-13H2,1-3H3,(H,27,28)
comment: Pemigatinib (INCB54828) is a FGFR inhibitor claimed in Incyte Corporation's patent WO2014007951 <Reference id=34085/>. It is equipotent at FGFR subtypes 1-3 <Reference id=34085/>.
iupac name: 3-(2,6-difluoro-3,5-dimethoxyphenyl)-1-ethyl-8-(morpholin-4-ylmethyl)-4,7-dihydropyrrolo[4,5]pyrido[1,2-d]pyrimidin-2-one
synonym: Pemazyre®
synonym: example 126 [WO2014007951]
synonym: INCB 54828
synonym: INCB54828
synonym: INCB-54828
synonym: INCB054828
approved: t
ligand name: pemigatinib
type: SyntheticOrganicLigand

peposertib
in ch i key: MOWXJLUYGFNTAL-DEOSSOPVSA-N
comment: Peposertib (M-3814) is an orally available inhibitor of DNA-dependent protein kinase (DNA-PK), that is being investiated for potential antineoplastic activity <Reference id=34082/>. Experimental evidence indicates that M-3814 potentiates the effect of radiotherapy in several xenotransplanted human tumour types <Reference id=34083/>, an effect that is being evaluated in human cancer patients in a clinical trial. The compound is claimed as example 136 in patent WO2014183850 <Reference id=34084/>.
iupac name: (S)-[2-chloro-4-fluoro-5-(7-morpholin-4-ylquinazolin-4-yl)phenyl]-(6-methoxypyridazin-3-yl)methanol
synonym: MSC2490484A
synonym: M3814
synonym: example 136 [WO2014183850]
synonym: nedisertib (deleted INN)
approved: f
ligand name: peposertib
type: SyntheticOrganicLigand

AZD1678
canonical SMILES: COc1nc(F)cnc1NS(=O)(=O)c1cccc(c1Cl)Cl
isomeric SMILES: COc1nc(F)cnc1NS(=O)(=O)c1cccc(c1Cl)Cl
in ch i key: NWSUDJQTTGDPIR-UHFFFAOYSA-N
comment: AZD1678 is a potent and bioavailable aminopyrazine sulfonamide CCR4 receptor antagonist discovered in a high-throughput screening/synthesis campaign <Reference id=33675/>
iupac name: 2,3-dichloro-N-(5-fluoro-3-methoxypyrazin-2-yl)benzenesulfonamide
synonym: AZD-1678
synonym: compound 49 [PMID: 28947948]
approved: f
ligand name: AZD1678
type: SyntheticOrganicLigand

mavelertinib
in ch i key: JYIUNVOCEFIUIU-GHMZBOCLSA-N
in ch i: InChI=1S/C18H22FN9O2/c1-5-13(29)21-11-8-28(6-10(11)19)18-23-15(14-16(24-18)26(2)9-20-14)22-12-7-27(3)25-17(12)30-4/h5,7,9-11H,1,6,8H2,2-4H3,(H,21,29)(H,22,23,24)/t10-,11-/m1/s1
comment: Mavelertinib (PF-06747775) is a third generation mutant EGFR receptor tyrosine kinase inhibitor that has potential antineoplastic activity <Reference id=34080/>. It is an irreversible inhibitor with selectivity for mutant EGFRs carrying the four common mutants (exon 19 deletion (Del), L858R, and double mutants T790M/L858R and T790M/Del) over wild-type EGFRs.
iupac name: N-[(3R,4R)-4-fluoro-1-[6-[(3-methoxy-1-methylpyrazol-4-yl)amino]-9-methylpurin-2-yl]pyrrolidin-3-yl]prop-2-enamide
synonym: compound 21 [PMID: 28287730]
synonym: PF-06747775
synonym: PF06747775
approved: f
ligand name: mavelertinib
type: SyntheticOrganicLigand

lanraplenib
in ch i key: XCIGZBVOUQVIPI-UHFFFAOYSA-N
in ch i: InChI=1S/C23H25N9O/c24-21-12-25-11-19(28-21)20-13-32-6-5-26-23(32)22(29-20)27-16-1-3-17(4-2-16)30-7-9-31(10-8-30)18-14-33-15-18/h1-6,11-13,18H,7-10,14-15H2,(H2,24,28)(H,27,29)
comment: Lanraplenib (GS-9876) was claimed as a Syk tyrosine kinase inhibitor in Gilead Sciences' patent US9290505 <Reference id=34079/>. Formal name>structure was disclosed in 2020 <Reference id=40905/>. Lanraplenib is in development for autoimmune diseases including SLE and Sjögren's syndrome.
iupac name: 6-(6-aminopyrazin-2-yl)-N-[4-[4-(oxetan-3-yl)piperazin-1-yl]phenyl]imidazo[1,2-a]pyrazin-8-amine
synonym: Ex.-2, US9290505
synonym: example 2 [US9290505]
synonym: GS-9876
synonym: GS9876
synonym: GS 9876
synonym: compound 39 [PMID: 32292557]
approved: f
ligand name: lanraplenib
type: SyntheticOrganicLigand

9-anthroic acid
canonical SMILES: OC(=O)c1c2ccccc2cc2c1cccc2
isomeric SMILES: OC(=O)c1c2ccccc2cc2c1cccc2
in ch i key: XGWFJBFNAQHLEF-UHFFFAOYSA-N
in ch i: InChI=1S/C15H10O2/c16-15(17)14-12-7-3-1-5-10(12)9-11-6-2-4-8-13(11)14/h1-9H,(H,16,17)
iupac name: anthracene-9-carboxylic acid
xref: CHEMBL1513985
synonym: anthracene-10-carboxylic acid
synonym: 9-AC
approved: f
ligand name: 9-anthroic acid
type: SyntheticOrganicLigand

conteltinib
in ch i key: NPJCURIANJMFEO-UHFFFAOYSA-N
in ch i: InChI=1S/C32H45N9O3S/c1-22(2)38-45(42,43)29-8-6-5-7-27(29)34-31-25-11-14-33-30(25)36-32(37-31)35-26-10-9-24(21-28(26)44-4)40-15-12-23(13-16-40)41-19-17-39(3)18-20-41/h5-10,21-23,38H,11-20H2,1-4H3,(H3,33,34,35,36,37)
comment: Conteltinib (CT-707) is a multikinase inhibitor with activity vs. FAK, ALK and Pyk2 tyrosine kinases <Reference id=34077/>. It is being developed by Centaurus Biopharma for antineoplastic potential.
iupac name: 2-[[2-[2-methoxy-4-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]anilino]-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidin-4-yl]amino]-N-propan-2-ylbenzenesulfonamide
synonym: US9428508, 96
synonym: example 96 [WO2012092880]
synonym: CT-707
synonym: CT707
synonym: CT 707
approved: f
ligand name: conteltinib
type: SyntheticOrganicLigand

example 31 (24) [WO2012005227]
in ch i key: RKUKGCKNRLOSDX-QAQDUYKDSA-N
comment: Ex_31 is a selective autotaxin (ATX, ENPP2) inhibitor <Reference id=34056/>. It is claimed as example 31(24) in patent WO2012005227 <Reference id=34057/>.
xref: CHEMBL3677653
synonym: Ex_31
approved: f
ligand name: example 31 (24) [WO2012005227]
type: SyntheticOrganicLigand

compound 9 [PMID: 26006010]
in ch i key: YELZMARZEBVKBL-VAZXNAHHSA-N
in ch i: InChI=1S/C33H35FN8O3/c1-33(2,40(3)23-18-44-19-23)15-21(16-35)32(43)41-13-7-8-22(41)17-42-31-28(30(36)37-20-38-31)29(39-42)26-12-11-25(14-27(26)34)45-24-9-5-4-6-10-24/h4-6,9-12,14-15,20,22-23H,7-8,13,17-19H2,1-3H3,(H2,36,37,38)/b21-15+/t22-/m0/s1
comment: Compound 9 [PMID: 26006010] is a reversible BTK inhibitor that was designed to have a long target residency time with a resulting increase in the duration of in vivo target engagement, and with the overall aim of improving in vivo drug efficacy <Reference id=34039/>. Compound 9 has a cysteine-reactive, inverted cyanoacrylamide scaffold structure that interacts with Cys481, a residue that lies outwith the catalytic domain of the enzyme but close to the ATP pocket (and is also a target of the irreversible inhibitor <Ligand id=6912/>). It has good aqueous solubility and is orally bioavailable. Compound 9 may be PRN473 as described in <Reference id=34040/>, but PRN473's structure has not been formally disclosed.
iupac name: (E)-2-[(2S)-2-[[4-amino-3-(2-fluoro-4-phenoxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]methyl]pyrrolidine-1-carbonyl]-4-methyl-4-[methyl(oxetan-3-yl)amino]pent-2-enenitrile
xref: CHEMBL3702836
approved: f
ligand name: compound 9 [PMID: 26006010]
type: SyntheticOrganicLigand

MP1104
in ch i key: WTIFKSFIQUZRRN-FMDQGZFPSA-N
in ch i: InChI=1S/C27H27IN2O3/c28-18-3-1-2-17(12-18)26(32)29-20-8-7-19-21-13-16-6-9-22(31)24-23(16)27(19,25(20)33-24)10-11-30(21)14-15-4-5-15/h1-3,6-9,12,15,19-21,25,31H,4-5,10-11,13-14H2,(H,29,32)/t19?,20-,21-,25+,27+/m1/s1
comment: Dual κ receptor/δ receptor agonist <Reference id=34025/>.
approved: f
ligand name: MP1104
type: SyntheticOrganicLigand

methylmalonic acid
canonical SMILES: CC(C(=O)O)C(=O)O
isomeric SMILES: CC(C(=O)O)C(=O)O
in ch i key: ZIYVHBGGAOATLY-UHFFFAOYSA-N
in ch i: InChI=1S/C4H6O4/c1-2(3(5)6)4(7)8/h2H,1H3,(H,5,6)(H,7,8)
comment: Succinate receptor agonist
iupac name: 2-methylpropanedioic acid
approved: f
ligand name: methylmalonic acid
type: SyntheticOrganicLigand

PBT-3
isomeric SMILES: CCCCC/C=C/CC(C(C1CC1)[C@H](/C=C/C/C=C/CCCC(=O)OC)O)C1CC1
in ch i key: ODNVBPFEZJHAAU-OBNWJGEWSA-N
in ch i: InChI=1S/C27H44O3/c1-3-4-5-6-9-12-15-24(22-18-19-22)27(23-20-21-23)25(28)16-13-10-7-8-11-14-17-26(29)30-2/h7-9,12-13,16,22-25,27-28H,3-6,10-11,14-15,17-21H2,1-2H3/b8-7-,12-9-,16-13-/t24?,25-,27?/m0/s1
comment: PBT-3 is a stable hepoxilin analogue, that antagonises hepoxilin effects in vitro and in vivo <Reference id=34012/><Reference id=34013/>. Hepoxilin A3 is an unstable lipid mediator (a proinflammatory eicosanoid derived from arachadonic acid) that acts as a potent neutrophil chemoattractant in the acute phase of the inflammatory response, and has been implicated in the process of NETosis by human neutrophils <Reference id=34016/>.
iupac name: methyl (5Z,8Z,10S,14Z)-11,12-dicyclopropyl-10-hydroxyicosa-5,8,14-trienoate
approved: f
ligand name: PBT-3
type: SyntheticOrganicLigand

mofegiline
canonical SMILES: NCC(=CF)CCc1ccc(cc1)F
isomeric SMILES: NC/C(=C/F)/CCc1ccc(cc1)F
in ch i key: VXLBSYHAEKDUSU-JXMROGBWSA-N
in ch i: InChI=1S/C11H13F2N/c12-7-10(8-14)2-1-9-3-5-11(13)6-4-9/h3-7H,1-2,8,14H2/b10-7+
comment: Mofegiline was originally identified as a monoamine oxidase B inhibitor <Reference id=34010/><Reference id=34008/>. Subsequently it has also been identified as an allylamine type irreversible, mechanism-based inhibitor of SSAO/VAP-1 enzyme activity <Reference id=34009/><Reference id=34004/>. It has antiinflammatory effects in vitro and in vivo. However mofegiline lacks the selectivity exhibited by more recently developed inhibitors such as <Ligand id=9753/>.
iupac name: (2E)-2-(fluoromethylidene)-4-(4-fluorophenyl)butan-1-amine
xref: CHEMBL489079
synonym: MDL-72,974
synonym: MDL 72974
synonym: MDL-72974A
approved: f
ligand name: mofegiline
type: SyntheticOrganicLigand

PXS-4681A
canonical SMILES: NCC(=CF)COc1ccc(cc1)S(=O)(=O)N
isomeric SMILES: NC/C(=C/F)/COc1ccc(cc1)S(=O)(=O)N
in ch i key: GJRSZKOPZAJCGZ-VMPITWQZSA-N
in ch i: InChI=1S/C10H13FN2O3S/c11-5-8(6-12)7-16-9-1-3-10(4-2-9)17(13,14)15/h1-5H,6-7,12H2,(H2,13,14,15)/b8-5+
comment: PXS-4681A is reported as a potent, selective and irreversible inhibitor of semicarbazide-sensitive amine oxidase (SSAO; also known as vascular adhesion protein-1 or VAP-1) with drug-like properties <Reference id=34004/> (note that the compound was synthesised as the hydrochloride salt and that we show the chemical structure for the parent molecule). PXS-4681A has antiinflammatory effects in vitro and in vivo <Reference id=34005/><Reference id=34004/>.
iupac name: 4-[(E)-2-(aminomethyl)-3-fluoroprop-2-enoxy]benzenesulfonamide
approved: f
ligand name: PXS-4681A
type: SyntheticOrganicLigand

evobrutinib
in ch i key: QUIWHXQETADMGN-UHFFFAOYSA-N
in ch i: InChI=1S/C25H27N5O2/c1-2-22(31)30-14-12-18(13-15-30)16-27-25-23(24(26)28-17-29-25)19-8-10-21(11-9-19)32-20-6-4-3-5-7-20/h2-11,17-18H,1,12-16H2,(H3,26,27,28,29)
comment: Evobrutinib is a Bruton's tyrosine kinase Inhibitor discovered by Merck, that has clinical potential across multiple autoimmune conditions (including rheumatoid arthritis, systemic lupus erythematosus, multiple sclerosis) <Reference id=38160/>. it is an orally active, ootent, and highly selective inhibitor with a covalent binding mode. The chemical structure is claimed as A250 in patent WO2012170976 <Reference id=33999/>.
iupac name: 1-[4-[[[6-amino-5-(4-phenoxyphenyl)pyrimidin-4-yl]amino]methyl]piperidin-1-yl]prop-2-en-1-one
synonym: MSC 2364447
synonym: M-2951
synonym: MSC-2364447C
synonym: M2951
synonym: MSC2364447C
synonym: A250 [WO2012170976]
approved: f
ligand name: evobrutinib
type: SyntheticOrganicLigand

necrostatin-1s
canonical SMILES: CN1C(=O)C(NC1=O)Cc1c[nH]c2c1cccc2Cl
isomeric SMILES: CN1C(=O)C(NC1=O)Cc1c[nH]c2c1cccc2Cl
in ch i key: WIKGAEMMNQTUGL-UHFFFAOYSA-N
in ch i: InChI=1S/C13H12ClN3O2/c1-17-12(18)10(16-13(17)19)5-7-6-15-11-8(7)3-2-4-9(11)14/h2-4,6,10,15H,5H2,1H3,(H,16,19)
comment: Necrostatin-1s is a more stable analogue of <Ligand id=9750/>, that is more appropriate for in vivo investigations <Reference id=33997/>.
iupac name: 5-[(7-chloro-1H-indol-3-yl)methyl]-3-methylimidazolidine-2,4-dione
xref: CHEMBL381230
synonym: necrostatin 2 racemate
synonym: nec-1s
synonym: 7-Cl-O-Nec-1
approved: f
ligand name: necrostatin-1s
type: SyntheticOrganicLigand

necrostatin-1
canonical SMILES: S=C1NC(C(=O)N1C)Cc1c[nH]c2c1cccc2
isomeric SMILES: S=C1NC(C(=O)N1C)Cc1c[nH]c2c1cccc2
in ch i key: TXUWMXQFNYDOEZ-UHFFFAOYSA-N
in ch i: InChI=1S/C13H13N3OS/c1-16-12(17)11(15-13(16)18)6-8-7-14-10-5-3-2-4-9(8)10/h2-5,7,11,14H,6H2,1H3,(H,15,18)
comment: Necrostatin-1 is an inhibitor of necroptosis <Reference id=33995/>. It inhibits RIPK1 <Reference id=33996/> and IDO <Reference id=33998/> enzyme activities <Reference id=33997/>.
iupac name: 5-(1H-indol-3-ylmethyl)-3-methyl-2-sulfanylideneimidazolidin-4-one
xref: CHEMBL195008
synonym: nec-1
synonym: MTH-DL-tryptophan
synonym: Necrostatin 1
synonym: methyl-thiohydantoin-tryptophan
synonym: MTH-trp
approved: f
ligand name: necrostatin-1
type: SyntheticOrganicLigand

6E11
in ch i key: OUAZLWHOOTXVCE-UHFFFAOYSA-N
in ch i: InChI=1S/C23H20O6/c1-27-18-11-19(24)22-20(25)13-23(26,29-21(22)12-18)16-7-9-17(10-8-16)28-14-15-5-3-2-4-6-15/h2-12,24,26H,13-14H2,1H3
comment: 6E11 is a non-ATP competitive, small molecule, selective inhibitor of the necroptosis-related enzyme receptor interacting serine/threonine kinase 1 (RIPK1) <Reference id=33994/>. It was identified using a phenotypic cell-based assay designed to detect the ability of test compounds to inhibit TNF-driven necrotic death. Although 6E11 is less potent than <Ligand id=9751/> in vitro, it provides a novel core for structural optimization.
iupac name: 2-[4-(benzyloxy)phenyl]-2,5-dihydroxy-7-methoxy-3,4-dihydro-2H-1-benzopyran-4-one
approved: f
ligand name: 6E11
type: SyntheticOrganicLigand

BMS-986187
in ch i key: UEKIYVKPQNKSDI-UHFFFAOYSA-N
in ch i: InChI=1S/C31H34O4/c1-19-8-6-7-9-21(19)18-34-22-12-10-20(11-13-22)27-28-23(32)14-30(2,3)16-25(28)35-26-17-31(4,5)15-24(33)29(26)27/h6-13,27H,14-18H2,1-5H3
comment: PAM for the δ-opioid receptor.
iupac name: 3,3,6,6-tetramethyl-9-[4-[(2-methylphenyl)methoxy]phenyl]-4,5,7,9-tetrahydro-2H-xanthene-1,8-dione
approved: f
ligand name: BMS-986187
type: SyntheticOrganicLigand

tolimidone
canonical SMILES: Cc1cccc(c1)Oc1cnc(=O)[nH]c1
isomeric SMILES: Cc1cccc(c1)Oc1cnc(=O)[nH]c1
in ch i key: HJQILFPVRNHTIG-UHFFFAOYSA-N
in ch i: InChI=1S/C11H10N2O2/c1-8-3-2-4-9(5-8)15-10-6-12-11(14)13-7-10/h2-7H,1H3,(H,12,13,14)
comment: Tolimidone is a potent and selective allosteric activator of Lyn kinase <Reference id=31995/>. It was developed for the treatment of type 2 diabetes.
iupac name: 5-(3-methylphenoxy)-1H-pyrimidin-2-one
xref: CHEMBL8030
synonym: MLR-1023
synonym: CP-26154
approved: f
ligand name: tolimidone
type: SyntheticOrganicLigand

AT-403
in ch i key: IGSSUIQLZJANKJ-QIDMFYOTSA-N
in ch i: InChI=1S/C25H37N3O2/c1-17(2)18-8-10-19(11-9-18)27-14-12-20(13-15-27)28-23-7-5-4-6-21(23)22(25(28)30)16-24(29)26-3/h4-7,17-20,22H,8-16H2,1-3H3,(H,26,29)/t18-,19+,22?
comment: NOP receptor-selective nonpeptide agonist <Reference id=33985/>.
iupac name: 2-(1-(1-((1s,4s)-4-isopropylcyclohexyl)piperidin-4-yl)-2-oxoindolin-3-yl)-N-methylacetamide
approved: f
ligand name: AT-403
type: SyntheticOrganicLigand

NDT9513727
in ch i key: ITACCRHKSPSKKL-UHFFFAOYSA-N
in ch i: InChI=1S/C36H35N3O4/c1-2-3-18-39-30(35(28-10-6-4-7-11-28)37-36(39)29-12-8-5-9-13-29)23-38(21-26-14-16-31-33(19-26)42-24-40-31)22-27-15-17-32-34(20-27)43-25-41-32/h4-17,19-20H,2-3,18,21-25H2,1H3
comment: NDT9513727 is a non-peptide inverse agonist of C5aR1 <Reference id=33984/>.
iupac name: N,N-bis(1,3-benzodioxol-5-ylmethyl)-1-[3-butyl-2,5-di(phenyl)imidazol-4-yl]methanamine
synonym: NDT 9513727
synonym: NDT-9513727
approved: f
ligand name: NDT9513727
type: SyntheticOrganicLigand

macimorelin
in ch i key: UJVDJAPJQWZRFR-DHIUTWEWSA-N
in ch i: InChI=1S/C26H30N6O3/c1-26(2,27)25(35)31-22(11-16-13-28-20-9-5-3-7-18(16)20)24(34)32-23(30-15-33)12-17-14-29-21-10-6-4-8-19(17)21/h3-10,13-15,22-23,28-29H,11-12,27H2,1-2H3,(H,30,33)(H,31,35)(H,32,34)/t22-,23-/m1/s1
comment: Macimorelin is a ghrelin peptidomimetic <Reference id=33980/>. It is a growth hormone (GH) secretagogue. The approved drug is the acetate salt (PubChem CID 71526737)- we show the parent molecule in this entry.
iupac name: 2-amino-N-[(2R)-1-[[(1R)-1-formamido-2-(1H-indol-3-yl)ethyl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]-2-methylpropanamide
xref: CHEMBL278623
synonym: EP-1572
synonym: EP1572
synonym: AEZS-130
synonym: AEZS130
synonym: Aib-DTrp-DgTrp-CHO
synonym: UMV1843
approved: t
ligand name: macimorelin
type: SyntheticOrganicLigand

lodoxamide
in ch i key: RVGLGHVJXCETIO-UHFFFAOYSA-N
in ch i: InChI=1S/C11H6ClN3O6/c12-7-5(14-8(16)10(18)19)1-4(3-13)2-6(7)15-9(17)11(20)21/h1-2H,(H,14,16)(H,15,17)(H,18,19)(H,20,21)
comment: Lodoxamide is a mast cell stabilizing anti-inflammatory drug. Clinically administered forms may contain lodoxamide trometamol/tromethamine.
iupac name: 2-[[2-chloro-5-cyano-3-(oxaloamino)phenyl]amino]-2-oxoacetic acid
xref: CHEMBL1201266
synonym: Alomide®
approved: t
ligand name: lodoxamide
type: SyntheticOrganicLigand

compound 83 [PMID: 23888932]
in ch i key: GDUANFXPOZTYKS-UHFFFAOYSA-N
comment: Compound 83 is a high affinity GPR35 agonist <Reference id=33966/>.
iupac name: 6-bromo-8-[(2,6-difluoro-4-methoxybenzoyl)amino]-4-oxochromene-2-carboxylic acid
xref: CHEMBL2425821
approved: f
ligand name: compound 83 [PMID: 23888932]
type: SyntheticOrganicLigand

CID2745687
in ch i key: CYNLZIBKERMMOA-UHFFFAOYSA-N
comment: CID2745687 is an antagonist of the orphan GPCR, GPR35 <Reference id=11745/>, that is a suitable chemical probe to help elucidate GPR35 pharmacolology.
iupac name: methyl 5-[(tert-butylcarbamothioylhydrazinylidene)methyl]-1-(2,4-difluorophenyl)pyrazole-4-carboxylate
xref: CHEMBL1708510
synonym: AC1MCK4S
synonym: compound 13 [PMID: 23888932]
approved: f
ligand name: CID2745687
type: SyntheticOrganicLigand

P218
canonical SMILES: CCc1nc(N)nc(c1OCCCOc1ccccc1CCC(=O)O)N
isomeric SMILES: CCc1nc(N)nc(c1OCCCOc1ccccc1CCC(=O)O)N
in ch i key: VDGXZSSDCDPCRF-UHFFFAOYSA-N
in ch i: InChI=1S/C18H24N4O4/c1-2-13-16(17(19)22-18(20)21-13)26-11-5-10-25-14-7-4-3-6-12(14)8-9-15(23)24/h3-4,6-7H,2,5,8-11H2,1H3,(H,23,24)(H4,19,20,21,22)
comment: The antifolate compound P218 is a potent and selective inhibitor of P. falciparum bifunctional dihydrofolate reductase-thymidylate synthase (PfDHFR-TS) and was designed to overcome the emergence of parasite resistance to this class of antimalarial compound <Reference id=34001/>. The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
iupac name: 3-[2-[3-(2,4-diamino-6-ethylpyrimidin-5-yl)oxypropoxy]phenyl]propanoic acid
xref: CHEMBL3040038
synonym: MMV000147
approved: f
ligand name: P218
type: SyntheticOrganicLigand

fosmidomycin
canonical SMILES: O=CN(CCCP(=O)(O)O)O
isomeric SMILES: O=CN(CCCP(=O)(O)O)O
in ch i key: GJXWDTUCERCKIX-UHFFFAOYSA-N
in ch i: InChI=1S/C4H10NO5P/c6-4-5(7)2-1-3-11(8,9)10/h4,7H,1-3H2,(H2,8,9,10)
comment: Fosmidomycin was first identified as antibacterial but also has antimalarial activity. The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
iupac name: 3-(formyl-hydroxyamino)propylphosphonic acid
xref: CHEMBL203125
synonym: FR-31564
synonym: FR 31564
approved: f
ligand name: fosmidomycin
type: NaturalProductLigand

tectorigenin
canonical SMILES: COc1c(O)cc2c(c1O)c(=O)c(co2)c1ccc(cc1)O
isomeric SMILES: COc1c(O)cc2c(c1O)c(=O)c(co2)c1ccc(cc1)O
in ch i key: OBBCRPUNCUPUOS-UHFFFAOYSA-N
in ch i: InChI=1S/C16H12O6/c1-21-16-11(18)6-12-13(15(16)20)14(19)10(7-22-12)8-2-4-9(17)5-3-8/h2-7,17-18,20H,1H3
comment: Tectorigenin is a plant derived isoflavone that has been shown to protect mammalian cells against oxidative, hydrogen peroxide-induced damage, by activating catalase <Reference id=33950/>.
iupac name: 5,7-dihydroxy-3-(4-hydroxyphenyl)-6-methoxychromen-4-one
approved: f
ligand name: tectorigenin
type: SyntheticOrganicLigand

cis-1,2-cyclopropanedicarboxylic acid
canonical SMILES: OC(=O)C1CC1C(=O)O
isomeric SMILES: OC(=O)[C@@H]1C[C@@H]1C(=O)O
in ch i key: RLWFMZKPPHHHCB-WSOKHJQSSA-N
in ch i: InChI=1S/C5H6O4/c6-4(7)2-1-3(2)5(8)9/h2-3H,1H2,(H,6,7)(H,8,9)/t2-,3+
comment: Succinate receptor agonist
iupac name: (1S,2R)-cyclopropane-1,2-dicarboxylic acid
approved: f
ligand name: cis-1,2-cyclopropanedicarboxylic acid
type: SyntheticOrganicLigand

M5717
in ch i key: BENUHBSJOJMZEE-UHFFFAOYSA-N
in ch i: InChI=1S/C27H31FN4O2/c28-22-7-8-25-23(17-22)24(27(33)29-9-12-31-10-1-2-11-31)18-26(30-25)21-5-3-20(4-6-21)19-32-13-15-34-16-14-32/h3-8,17-18H,1-2,9-16,19H2,(H,29,33)
comment: M5717 (formerly DDD498) is a quinoline-4-carboxamide derivative that is the optimised lead developed from a phenotypic screen for novel antimalarial drugs and has advanced to clinical evaluation. The compound was awarded MMV Project of the Year (2014). The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
iupac name: 6-fluoro-2-[4-(morpholin-4-ylmethyl)phenyl]-N-(2-pyrrolidin-1-ylethyl)quinoline-4-carboxamide
xref: CHEMBL4091762
synonym: DDD107498
synonym: MMV121
synonym: DDD498
approved: f
ligand name: M5717
type: SyntheticOrganicLigand

iguratimod
in ch i key: ANMATWQYLIFGOK-UHFFFAOYSA-N
in ch i: InChI=1S/C17H14N2O6S/c1-26(22,23)19-13-8-15-12(17(21)14(9-24-15)18-10-20)7-16(13)25-11-5-3-2-4-6-11/h2-10,19H,1H3,(H,18,20)
comment: Iguratimod is a methanesulfonanilide disease-modifying anti-rheumatic drug <Reference id=33921/><Reference id=33922/><Reference id=33923/>. Evidence from a mouse colitis model shows an anti-inflammatory effect of iguratimod, partly via regulation of Th17/Treg cells <Reference id=33924/>, that suggest iguratimod as a novel therapeutic for the treatment of IBD.
iupac name: N-[7-methanesulfonamido-4-oxo-6-(phenoxy)chromen-3-yl]formamide
xref: CHEMBL2107455
synonym: T-614
synonym: Careram®
synonym: Kolbet®
synonym: Iremod
approved: t
ligand name: iguratimod
type: SyntheticOrganicLigand

trodusquemine
in ch i key: WUJVPODXELZABP-FWJXURDUSA-N
in ch i: InChI=1S/C37H72N4O5S/c1-26(2)34(46-47(43,44)45)13-10-27(3)30-11-12-31-35-32(15-17-37(30,31)5)36(4)16-14-29(24-28(36)25-33(35)42)41-23-9-22-40-20-7-6-19-39-21-8-18-38/h26-35,39-42H,6-25,38H2,1-5H3,(H,43,44,45)/t27-,28-,29+,30-,31+,32+,33-,34-,35+,36+,37-/m1/s1
comment: Trodusquemine is a naturally-occurring compound that acts as an allosteric (noncompetitive) inhibitor of protein tyrosine phosphatase 1B (PTPN1) <Reference id=33915/>. PTPN1 inhibitors are being evaluated for potential anti-type 2 diabetes effects.
xref: CHEMBL508583
synonym: MSI-1436
synonym: MSI1436
approved: f
ligand name: trodusquemine
type: NaturalProductLigand

HPN
in ch i key: ZBDKXZCSKUHAPY-UHFFFAOYSA-N
in ch i: InChI=1S/C17H17Br3O5/c1-7(2)25-6-9-5-12(22)16(23)14(19)10(9)3-8-4-11(21)17(24)15(20)13(8)18/h4-5,7,21-24H,3,6H2,1-2H3
comment: HPN is a synthetic bromophenol analogue of the algal-derived compound, BPN (PubChem CID10995003). It acts as a competitive inhibitor of the type 2 diabetes target, protein tyrosine phosphatase 1B (PTP1B; gene symbol PTPN1) <Reference id=33911/>. HPN is cell permeable and orally active, and exhibits a hypoglycaemic effect in animal models <Reference id=33912/>.
iupac name: 3,4-dibromo-5-[[2-bromo-3,4-dihydroxy-6-(propan-2-yloxymethyl)phenyl]methyl]benzene-1,2-diol
approved: f
ligand name: HPN
type: SyntheticOrganicLigand

benzodrocortisone
in ch i key: LPEYMYDYPGRLBU-YGZHYJPASA-N
in ch i: InChI=1S/C28H34O6/c1-26-12-10-19(30)14-18(26)8-9-20-21-11-13-28(23(32)16-29,27(21,2)15-22(31)24(20)26)34-25(33)17-6-4-3-5-7-17/h3-7,14,20-22,24,29,31H,8-13,15-16H2,1-2H3/t20-,21-,22-,24+,26-,27-,28-/m0/s1
comment: Benzodrocortisone is a synthetic glucocorticosteroid <Reference id=33910/>.
iupac name: [(8S,9S,10R,11S,13S,14S,17R)-11-hydroxy-17-(2-hydroxy-acetyl)-10,13-dimethyl-3-oxo-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-17-yl] benzoate
synonym: hydrocortisone 17-benzoate
synonym: compound 1 [WO2013071010]
approved: f
ligand name: benzodrocortisone
type: SyntheticOrganicLigand

atogepant
in ch i key: QIVUCLWGARAQIO-OLIXTKCUSA-N
in ch i: InChI=1S/C29H23F6N5O3/c1-13-16(22-18(30)4-5-19(31)23(22)32)8-20(26(42)40(13)12-29(33,34)35)38-25(41)15-7-14-9-28(10-21(14)37-11-15)17-3-2-6-36-24(17)39-27(28)43/h2-7,11,13,16,20H,8-10,12H2,1H3,(H,38,41)(H,36,39,43)/t13-,16-,20+,28+/m1/s1
comment: Atogepant is an oral calcitonin gene-related peptide receptor (CGRP) antagonist that that was doscovered by Merck, and which is now being developed by Allergan as prophylaxis of migraine <Reference id=33909/>.
iupac name: (3S)-N-[(3S,5S,6R)-6-methyl-2-oxo-1-(2,2,2-trifluoroethyl)-5-(2,3,6-trifluorophenyl)piperidin-3-yl]-2-oxospiro[1H-pyrrolo[2,3-b]pyridine-3,6'-5,7-dihydrocyclopenta[b]pyridine]-3'-carboxamide
synonym: MK-8031
synonym: AGN-241689
synonym: example 4 [US20120122911]
synonym: Qulipta®
approved: t
ligand name: atogepant
type: SyntheticOrganicLigand

dezapelisib
in ch i key: RSIWALKZYXPAGW-NSHDSACASA-N
in ch i: InChI=1S/C20H16FN7OS/c1-10-7-30-20-27-15(11(2)26-18-16-17(23-8-22-16)24-9-25-18)14(19(29)28(10)20)12-4-3-5-13(21)6-12/h3-9,11H,1-2H3,(H2,22,23,24,25,26)/t11-/m0/s1
comment: Dezapelisib (INCB 40093) is a potent and selective PIK3δ inhibitor that was being developed as a potential therapy for B cell malignancies <Reference id=22543/>. Claimed as example 15 in patent WO2011008487, although only binned IC50 values are contained in this patent document <Reference id=33905/>.
iupac name: 6-(3-fluorophenyl)-3-methyl-7-[(1S)-1-(7H-purin-6-ylamino)ethyl]-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one
xref: CHEMBL2216863
synonym: INCB 40093
synonym: compound 67 [PMID: 22924688]
synonym: example 15 [WO2011008487]
synonym: INCB40093
approved: f
ligand name: dezapelisib
type: SyntheticOrganicLigand

mocravimod
in ch i key: IINUNQPYJGJCJI-UHFFFAOYSA-N
in ch i: InChI=1S/C24H26ClNO3S/c25-23-14-22(10-9-19(23)11-12-24(26,16-27)17-28)30-21-8-4-7-20(13-21)29-15-18-5-2-1-3-6-18/h1-10,13-14,27-28H,11-12,15-17,26H2
comment: Mocravimod (KRP-203) is a sphingosine 1-phosphate receptor type 1 (S1P1R) agonist with immunomodulatory potential <Reference id=33902/>. It is a highly modified analogue of the approved MS drug <Ligand id=2407/>.
iupac name: 2-Amino-2-(2-(2-chloro-4-(3-benzyloxyphenylthio)phenyl)ethyl)-1,3-propanediol
xref: CHEMBL2137148
synonym: KRP-203
synonym: KRP203
synonym: compound 2 [PMID: 23124563]
approved: f
ligand name: mocravimod
type: SyntheticOrganicLigand

MMV048
in ch i key: RTJQABCNNLMCJF-UHFFFAOYSA-N
comment: MMV048 is the optimised lead compound for the 2-aminopyridines, a class of small molecules with promising antimalarial activity <Reference id=34449/>. The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
iupac name: 5-(4-methylsulfonylphenyl)-3-[6-(trifluoromethyl)pyridin-3-yl]pyridin-2-amine
xref: CHEMBL2041980
synonym: MMV390048
approved: f
ligand name: MMV048
type: SyntheticOrganicLigand

tropifexor
in ch i key: VYLOOGHLKSNNEK-PIIMJCKOSA-N
comment: Tropifexor (LJN452) is a potent non-bile acid agonist of the ligand-activated nuclear farnesoid X receptor (FXR) <Reference id=33897/> that is being developed by Novartis.
iupac name: 2-[(1R,3r,5S)-3-({5-cyclopropyl-3-[2-(trifluoromethoxy)phenyl]-1,2-oxazol-4-yl}methoxy)-8-azabicyclo[3.2.1]octan-8-yl]-4-fluoro-1,3-benzothiazole-6-carboxylic acid
synonym: LJN452
synonym: compound 1 [PMID: 29148806]
approved: f
ligand name: tropifexor
type: SyntheticOrganicLigand

semaglutide
in ch i key: DLSWIYLPEUIQAV-CCUURXOWSA-N
comment: Semaglutide is a glucagon like peptide 1 (GLP-1) receptor peptidomimetic agonist <Reference id=33890/>. Structurally it is a modified analogue of <Ligand id=3544/> with amino acids at positions 8 and 34 replaced by α-aminobutyric acid and arginine respectively, and Lys26 is acylated with stearic diacid. Semaglutide has slightly lower GLP-1 receptor affinity than <Ligand id=1133/>, but this is compensated by an increased serum albumin affinity, which ensures improved resistance to metabolic degradation.
synonym: Rybelsus® (oral semaglutide)
synonym: Ozempic® (injectable semaglutide)
synonym: NN9535
synonym: NN-9535
synonym: NN 9535
synonym: Wegovy®
approved: t
ligand name: semaglutide
type: PeptideLigand

(+)-SJ733
in ch i key: VKCPFWKTFZAOTO-LEWJYISDSA-N
in ch i: InChI=1S/C24H16F4N4O2/c25-19-8-7-16(10-15(19)11-29)31-22(33)20-17-5-1-2-6-18(17)23(34)32(13-24(26,27)28)21(20)14-4-3-9-30-12-14/h1-10,12,20-21H,13H2,(H,31,33)/t20-,21+/m0/s1
comment: (+)-SJ733 is the optimized lead for the dihydroisoquinolones (DHIQ), a novel chemotype with antimalarial activity <Reference id=34000/>. The (+)-enantiomer, shown here, has a significantly higher antimalarial potency <Reference id=34000/>. The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
iupac name: (3S,4S)-N-(3-cyano-4-fluorophenyl)-1-oxo-3-pyridin-3-yl-2-(2,2,2-trifluoroethyl)-3,4-dihydroisoquinoline-4-carboxamide
xref: CHEMBL4207489
synonym: (+)-SJ557733
synonym: SJ 733
synonym: SJ-733
synonym: SJ-557733
synonym: SJ 557733
synonym: SJ-000557733
synonym: (+)-SJ000557733
synonym: SJ 000557733
synonym: SJ733
approved: f
ligand name: (+)-SJ733
type: SyntheticOrganicLigand

tafenoquine
in ch i key: LBHLFPGPEGDCJG-UHFFFAOYSA-N
in ch i: InChI=1S/C24H28F3N3O3/c1-14-11-20(32-4)30-22-18(29-15(2)7-6-10-28)13-19(31-3)23(21(14)22)33-17-9-5-8-16(12-17)24(25,26)27/h5,8-9,11-13,15,29H,6-7,10,28H2,1-4H3
comment: Tafenoquine is an 8-aminoquinoline derivative that has potent antimalarial activity and is a synthetic analogue of <Ligand id=9952/>. The INN record for tafenoquine indicates that it is a racemic mixture. We show the chemical structure without stereochemistry to represent the mixture. The non-isomeric structure is also represented in the PubChem and ChEMBL entries listed in the links table below, while the two enantiomers forming the racemate are represented by PubChem CID 76969187 and PubChem CID 76969188. The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
iupac name: N-[2,6-dimethoxy-4-methyl-5-[3-(trifluoromethyl)phenoxy]quinolin-8-yl]pentane-1,4-diamine
xref: CHEMBL298470
synonym: WR238605
synonym: Arakoda®
synonym: Krintafel®
synonym: etaquine
approved: t
ligand name: tafenoquine
type: SyntheticOrganicLigand

cipargamin
in ch i key: CKLPLPZSUQEDRT-WPCRTTGESA-N
comment: Cipargamin is an antimalarial drug candidate, under clinical development. It is the optimised lead for the spiroindolones, a novel class of compounds identified from a phenotypic screen as having antimalarial activity <Reference id=34118/><Reference id=33889/> and awarded MMV Project of the Year (2009). The active enantiomer is shown here, with the 1R,3S configuration essential for antimalarial activity <Reference id=33889/>. The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
iupac name: (3R,3'S)-5,7'-dichloro-6'-fluoro-3'-methylspiro[1H-indole-3,1'-2,3,4,9-tetrahydropyrido[3,4-b]indole]-2-one
xref: CHEMBL1082723
synonym: KAE609
synonym: NITD609
approved: f
ligand name: cipargamin
type: SyntheticOrganicLigand

cis-epoxysuccinic acid
canonical SMILES: OC(=O)C1OC1C(=O)O
isomeric SMILES: OC(=O)[C@@H]1O[C@@H]1C(=O)O
in ch i key: DCEMCPAKSGRHCN-XIXRPRMCSA-N
in ch i: InChI=1S/C4H4O5/c5-3(6)1-2(9-1)4(7)8/h1-2H,(H,5,6)(H,7,8)/t1-,2+
comment: Succinate receptor agonist.
iupac name: (2R,3S)-oxirane-2,3-dicarboxylic acid
approved: f
ligand name: cis-epoxysuccinic acid
type: SyntheticOrganicLigand

BIRT 377
in ch i key: FJNJHZQMQRVZEE-GOSISDBHSA-N
comment: BIRT 377 is an orally active inhibitor of the LFA-1/ICAM-1 interaction <Reference id=33884/>.
iupac name: (5R)-5-[(4-bromophenyl)methyl]-3-(3,5-dichlorophenyl)-1,5-dimethylimidazolidine-2,4-dione
xref: CHEMBL367808
synonym: BIRT-377
synonym: BIRT377
approved: f
ligand name: BIRT 377
type: SyntheticOrganicLigand

BI-1950
in ch i key: JZTTUZXIQIRVAB-FZEVHQGJSA-N
comment: BI-1950 is a potent inhibitor of the LFA-1/ICAM-1 interaction. It is active in vitro and in vivo. This ligand is one of the compounds available from Boehringer Ingelheim's opnMe molecular library.
iupac name: (2S)-2-{[(3R)-3-[(4-cyanophenyl)methyl]-1-(3,5-dichloro-4-fluorophenyl)-3-methyl-2-oxo-1H,2H,3H-[1,3]diazolo[1,2-a]imidazol-5-yl]formamido}-N-[1-(pyridin-2-yl)cyclopropyl]propanamide
approved: f
ligand name: BI-1950
type: SyntheticOrganicLigand

GSK2256294
in ch i key: LQHDJQIMETZMPH-ZBFHGGJFSA-N
in ch i: InChI=1S/C21H24F3N7O/c1-12-28-19(26-2)31-20(29-12)30-16-5-3-4-14(9-16)18(32)27-11-15-7-6-13(10-25)8-17(15)21(22,23)24/h6-8,14,16H,3-5,9,11H2,1-2H3,(H,27,32)(H2,26,28,29,30,31)/t14-,16+/m1/s1
comment: GSK2256294 is an epoxide hydrolase 2 (sEH) inhibitor.
iupac name: (1R,3S)-N-(4-cyano-2-(trifluoromethyl)benzyl)-3-((4-methyl-6-(methylamino)-1,3,5-triazin-2-yl)amino)cyclohexane-1-carboxamide
xref: CHEMBL3818875
synonym: GSK-2256294
synonym: GSK2256294A
synonym: GSK-2256294A
approved: f
ligand name: GSK2256294
type: SyntheticOrganicLigand

BI-1935
in ch i key: KMESAVNRPDKZCQ-UHFFFAOYSA-N
in ch i: InChI=1S/C24H21F3N6O3/c1-2-36-11-10-32-15-17(5-8-22(32)34)23(35)30-21-7-6-18(14-29-21)33-20(24(25,26)27)12-19(31-33)16-4-3-9-28-13-16/h3-9,12-15H,2,10-11H2,1H3,(H,29,30,35)
comment: BI-1935 is a potent and selective small molecule inhibitor of epoxide hydrolase 2 (a.k.a. soluble epoxide hydrolase, sEH). It is claimed as Example 3 in Boehringer Ingelheim's patent WO2007067836 <Reference id=33875/>. This ligand is one of the compounds available from Boehringer Ingelheim's opnMe molecular library.
iupac name: 1-(2-ethoxyethyl)-6-oxo-N-[5-[3-pyridin-3-yl-5-(trifluoromethyl)pyrazol-1-yl]pyridin-2-yl]pyridine-3-carboxamide
synonym: example 3 [WO2007067836]
synonym: BI 1935
synonym: BI1935
approved: f
ligand name: BI-1935
type: SyntheticOrganicLigand

BI 665915
in ch i key: QGPXEIMWTKWHMH-UHFFFAOYSA-N
in ch i: InChI=1S/C24H26N8O2/c1-24(19-8-9-19,18-6-4-15(5-7-18)16-10-26-23(25)27-11-16)22-29-21(34-30-22)17-12-28-32(13-17)14-20(33)31(2)3/h4-7,10-13,19H,8-9,14H2,1-3H3,(H2,25,26,27)
comment: BI 665915 is a FLAP (5-lipoxygenase activating protein) inhibitor <Reference id=33868/>. This ligand is one of the compounds available from Boehringer Ingelheim's opnMe molecular library.
iupac name: 2-[4-(3-{1-[4-(2-aminopyrimidin-5-yl)phenyl]-1-cyclopropylethyl}-1,2,4-oxadiazol-5-yl)-1H-pyrazol-1-yl]-N,N-dimethylacetamide
synonym: compound 69 [PMID: 25671290]
synonym: BI-665915
synonym: BI665915
approved: f
ligand name: BI 665915
type: SyntheticOrganicLigand

BI 653048
in ch i key: AUIFRJWXYUNPPV-QFIPXVFZSA-N
comment: BI 653048 is a %22dissociated%22 glucocorticoid receptor (GR) agonist (displaying different transcriptional regulatory profiles between gene transrepression and transactivation). This type of drug is designed to reduce the unwanted side-effects common to traditional GR agonists <Reference id=33475/><Reference id=33863/>. It has favourable drug-like properties, but because it has reduced mouse functional transrepression potency it is not suitable for evaluation in standard preclinical mouse models. BI 653048 is synthesised as the phosphoric acid (H3PO4) cocrystal to optimise physicochemical properties, stability characteristics, solubility and bioavailability compared to the free form <Reference id=33862/>. This ligand is one of the compounds available from Boehringer Ingelheim's opnMe molecular library.
iupac name: (R)-2-(4-((5-(Ethylsulfonyl)-1H-pyrrolo[2,3-c]pyridin-2-yl)methyl)-5,5,5-trifluoro-4-hydroxy-2-methylpentan-2-yl)-5-fluorobenzamide
xref: CHEMBL3358954
synonym: (R)-39
synonym: BI-653048
synonym: BI653048
synonym: BI 653048 BS H3PO4
approved: f
ligand name: BI 653048
type: SyntheticOrganicLigand

BI-6901
in ch i key: BRJXJOWXAFLRTE-OAQYLSRUSA-N
in ch i: InChI=1S/C23H27N5O3S/c1-17-8-13-28(14-9-17)23(29)21(10-15-27-12-3-4-18(27)16-24)26-32(30,31)22-6-2-5-20-19(22)7-11-25-20/h2-7,11-12,17,21,25-26H,8-10,13-15H2,1H3/t21-/m1/s1
comment: BI-6901 is a selective inhibitor of the chemokine receptor CCR10 <Reference id=33853/>. This chemical structure is the active enantiomer (or eutomer) of the compound. The CCL27-CCR10 axis is a molecular target for the development of novel therapies for inflammatory skin conditions. This ligand is one of the compounds available from Boehringer Ingelheim's opnMe molecular library.
iupac name: 4-(2-cyano-1H-pyrrol-1-yl)-S-(1H-indol-4-yl)-1-(4-methylpiperidin-1-yl)-1-oxobutane-2-sulfonamido
synonym: eut-22
synonym: BI 6901
synonym: BI6901
approved: f
ligand name: BI-6901
type: SyntheticOrganicLigand

compound 5e [PMID: 28580438]
canonical SMILES: CC(Nc1ccnc(n1)Nc1cccc(c1)c1cccnc1)C
isomeric SMILES: CC(Nc1ccnc(n1)Nc1cccc(c1)c1cccnc1)C
in ch i key: JTFUPGNZUPRHCZ-UHFFFAOYSA-N
in ch i: InChI=1S/C18H19N5/c1-13(2)21-17-8-10-20-18(23-17)22-16-7-3-5-14(11-16)15-6-4-9-19-12-15/h3-13H,1-2H3,(H2,20,21,22,23)
comment: Compound 5e is a potent FMS-like tyrosine kinase 3 (FLT3, a type III receptor tyrosine kinase) inhibitor that is in preclinical evaluation for the treatment of acute myelogenous leukemia (AML) <Reference id=33821/>.
iupac name: N4-(propan-2-yl)-N2-[3-(pyridin-3-yl)phenyl]pyrimidine-2,4-diamine
approved: f
ligand name: compound 5e [PMID: 28580438]
type: SyntheticOrganicLigand

tibolone
in ch i key: WZDGZWOAQTVYBX-XOINTXKNSA-N
in ch i: InChI=1S/C21H28O2/c1-4-21(23)10-8-18-19-13(2)11-14-12-15(22)5-6-16(14)17(19)7-9-20(18,21)3/h1,13,17-19,23H,5-12H2,2-3H3/t13-,17-,18+,19-,20+,21+/m1/s1
comment: Tibolone is a synthetic anabolic steroid with estrogenic, androgenic and progestagenic activities.
iupac name: (7R,8R,9S,13S,14S,17R)-17-ethynyl-17-hydroxy-7,13-dimethyl-1,2,4,6,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-one
synonym: Livial
synonym: Tibofem
synonym: Boltin
synonym: Org OD 14
approved: t
ligand name: tibolone
type: SyntheticOrganicLigand

CPUY192018
in ch i key: KWSIQJUNYMMCTB-UHFFFAOYSA-N
comment: CPUY192018 binds to kelch like ECH associated protein 1 (KEAP1) and prevents its interaction with the transcription factor nuclear factor erythroid 2-related factor 2 (Nrf2; NFE2L2; Q16236) <Reference id=33811/><Reference id=36084/>. CPUY192018 acts as a functional Nrf2 activator. It binds non-covalently to KEAP1, unlike the approved Nrf2 activator <Ligand id=7045/> and the failed clinical lead <Ligand id=2717/>, which form irreversible, covalent bonds with a key cysteine residue in KEAP1 <Reference id=33810/>.
iupac name: 2-[[4-[carboxymethyl-(4-methoxyphenyl)sulfonylamino]naphthalen-1-yl]-(4-methoxyphenyl)sulfonylamino]acetic acid
synonym: compound 18e [PMID: 26258437]
synonym: compound 2 [PMID: 24512214]
approved: f
ligand name: CPUY192018
type: SyntheticOrganicLigand

STK16-IN-1
canonical SMILES: Fc1ccc(cc1C)n1c(=O)ccc2c1c1cc[nH]c1nc2
isomeric SMILES: Fc1ccc(cc1C)n1c(=O)ccc2c1c1cc[nH]c1nc2
in ch i key: WQNRDXHKVSKUPI-UHFFFAOYSA-N
in ch i: InChI=1S/C17H12FN3O/c1-10-8-12(3-4-14(10)18)21-15(22)5-2-11-9-20-17-13(16(11)21)6-7-19-17/h2-9H,1H3,(H,19,20)
comment: STK16-IN-1 is a selective inhibitor of serine/threonine kinase 16 (STK16) that can be used as a pharmacological tool to investigate the biological functions of STK16 <Reference id=33717/>. It is compound 219 in a 2010 patent claiming mTOR inhibitors <Reference id=33718/>.
iupac name: 1-(4-fluoro-3-methylphenyl)-7H-pyrrolo[2,3-h][1,6]naphthyridin-2-one
approved: f
ligand name: STK16-IN-1
type: SyntheticOrganicLigand

compound III [PMID: 24045148]
in ch i key: FPPVJOTXZIRXTF-UHFFFAOYSA-N
in ch i: InChI=1S/C23H34N4O/c1-15(2)27-21-14-17(4)16(3)13-20(21)25-23(27)26-11-9-18(10-12-26)22(28)24-19-7-5-6-8-19/h13-15,18-19H,5-12H2,1-4H3,(H,24,28)
comment: Compound III is an inhibitor of human and rat prostaglandin E synthase (PTGES, a.k.a. microsomal PGE synthase-1 or mPGES-1) <Reference id=33807/>. It is example 9 in patent WO2011023812, which claims >300 proposed mPGES-1 inhibitor structures <Reference id=33809/>.
iupac name: N-cyclopentyl-1-(5,6-dimethyl-1-propan-2-ylbenzimidazol-2-yl)piperidine-4-carboxamide
xref: CHEMBL3770411
approved: f
ligand name: compound III [PMID: 24045148]
type: SyntheticOrganicLigand

OSM-S-38
isomeric SMILES: FC(c1ccc(cc1)n1c(C)cc(c1C)/C=C/1/SC(=NC1=O)Nc1ccccc1)(F)F
in ch i key: YBBWTVGRVHTTDD-MOSHPQCFSA-N
in ch i: InChI=1S/C23H18F3N3OS/c1-14-12-16(15(2)29(14)19-10-8-17(9-11-19)23(24,25)26)13-20-21(30)28-22(31-20)27-18-6-4-3-5-7-18/h3-13H,1-2H3,(H,27,28,30)/b20-13-
comment: OSM-S-38 is an antimalarial lead, developed from a research collaboration employing an open source research mechanism <Reference id=33798/>. The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
iupac name: (5Z)-2-anilino-5-[[2,5-dimethyl-1-[4-(trifluoromethyl)phenyl]pyrrol-3-yl]methylidene]-1,3-thiazol-4-one
xref: CHEMBL2113938
approved: f
ligand name: OSM-S-38
type: SyntheticOrganicLigand

linrodostat
in ch i key: KRTIYQIPSAGSBP-KLAILNCOSA-N
in ch i: InChI=1S/C24H24ClFN2O/c1-15(24(29)28-20-9-6-18(25)7-10-20)16-2-4-17(5-3-16)21-12-13-27-23-11-8-19(26)14-22(21)23/h6-17H,2-5H2,1H3,(H,28,29)/t15-,16?,17?/m1/s1
comment: Linrodostat (BMS-986205) is a potent and selective, orally available indoleamine 2,3-dioxygenase 1 (IDO1) inhibitor <Reference id=38831/>, being investigated as an immuno-therapeutic for various malignancies. The INN for linrodostat specifies the (R) stereoisomer. The chemical structure is claimed as example 19 in Flexus Bioscience's patent US2016137652 <Reference id=33782/> and the compound is being taken through clinical development by Bristol-Myers Squibb. Mechanistically, linrodostat competes with the heme cofactor for binding to the apo-form of the enzyme, and once bound prevents heme from rebinding <Reference id=38831/>.
iupac name: (2R)-N-(4-chlorophenyl)-2-[4-(6-fluoroquinolin-4-yl)cyclohexyl]propanamide
synonym: BMS986205
synonym: Compound 2 [PMID: 29531094]
synonym: BMS-986205
synonym: Example 19 [US20160137652A1]
approved: f
ligand name: linrodostat
type: SyntheticOrganicLigand

JWH-018
canonical SMILES: CCCCCn1cc(c2c1cccc2)C(=O)c1cccc2c1cccc2
isomeric SMILES: CCCCCn1cc(c2c1cccc2)C(=O)c1cccc2c1cccc2
in ch i key: JDNLPKCAXICMBW-UHFFFAOYSA-N
in ch i: InChI=1S/C24H23NO/c1-2-3-8-16-25-17-22(20-13-6-7-15-23(20)25)24(26)21-14-9-11-18-10-4-5-12-19(18)21/h4-7,9-15,17H,2-3,8,16H2,1H3
comment: JWH-018 is a synthetic cannabinoid generated in the 1990s with limited selectivity between CB1 and CB2 receptors (original synthesis reported in: https://www.sciencedirect.com/science/article/pii/S0960894X01801554). In vivo, it displays the 'classical tetrad' activity of CB1 agonists, with analgesic, hypothermic, hypolocomotive and cataleptic properties <Reference id=34367/>. In the UK, it was the structural basis for definition of a series of compounds classified as Controlled Drugs under the Misuse of Drugs Act 1971 (Amendment) Order 2016 (see: https://www.legislation.gov.uk/ukdsi/2016/9780111148716). It is the non-fluorinated analogue of <Ligand id=9705/>.
xref: CHEMBL561013
synonym: JWH018
synonym: JWH 018
synonym: AM-678
approved: f
ligand name: JWH-018
type: SyntheticOrganicLigand

AM2201
in ch i key: ALQFAGFPQCBPED-UHFFFAOYSA-N
in ch i: InChI=1S/C24H22FNO/c25-15-6-1-7-16-26-17-22(20-12-4-5-14-23(20)26)24(27)21-13-8-10-18-9-2-3-11-19(18)21/h2-5,8-14,17H,1,6-7,15-16H2
comment: AM2201 is a highly potent synthetic cannabinoid <Reference id=33774/><Reference id=33775/>. Both acute and long-term AM2201 intoxication has serious side-effects and can be lethal <Reference id=33777/><Reference id=33776/>. AM2201 is the terminally fluorinated analogue of <Ligand id=9706/>.
iupac name: [1-(5-fluoropentyl)indol-3-yl]-naphthalen-1-ylmethanone
xref: CHEMBL3526578
synonym: AM-2201
approved: f
ligand name: AM2201
type: SyntheticOrganicLigand

VU6010608
in ch i key: YCDOKDADFOBKIL-UHFFFAOYSA-N
in ch i: InChI=1S/C18H15F3N4O4/c1-27-15-6-3-11(7-16(15)28-2)17(26)24-13-8-12(29-18(19,20)21)4-5-14(13)25-10-22-9-23-25/h3-10H,1-2H3,(H,24,26)
comment: VU6010608 is a selective, negative allosteric modulator (NAM) of metabotropic glutamate receptor mGlu7 <Reference id=33766/>, and represents a novel chemotype. VU6010608 is CNS penetrant and effective in electrophysiology studies making it an ideal tool compound suitable for investigating the physiology and therapeutic potential of mGlu7, however, its in vivo utility is limited by total and free levels achieved in the brain.
iupac name: 3,4-dimethoxy-N-[2-(1H-1,2,4-triazol-1-yl)-5-(trifluoromethoxy)phenyl]benzamide
synonym: compound 11a [Reed et al., 2017)
approved: f
ligand name: VU6010608
type: SyntheticOrganicLigand

tubastatin A
in ch i key: GOVYBPLHWIEHEJ-UHFFFAOYSA-N
in ch i: InChI=1S/C20H21N3O2/c1-22-11-10-19-17(13-22)16-4-2-3-5-18(16)23(19)12-14-6-8-15(9-7-14)20(24)21-25/h2-9,25H,10-13H2,1H3,(H,21,24)
comment: Tubastatin A is a selective histone deacetylase (HDAC) 6 inhibitor. It is claimed as example 6 in patent US8748451 <Reference id=33762/>.
iupac name: N-hydroxy-4-[(2-methyl-3,4-dihydro-1H-pyrido[4,3-b]indol-5-yl)methyl]benzamide
xref: CHEMBL2018302
approved: f
ligand name: tubastatin A
type: SyntheticOrganicLigand

CX549
in ch i key: QOVYHDHLFPKQQG-NDEPHWFRSA-N
in ch i: InChI=1S/C33H51N11O3/c34-28(32(46)47)12-13-30(45)43-20-14-25(15-21-43)38-31-27-10-4-5-11-29(27)39-33(40-31)37-22-26-23-44(42-41-26)19-7-17-35-16-6-18-36-24-8-2-1-3-9-24/h4-5,10-11,23-25,28,35-36H,1-3,6-9,12-22,34H2,(H,46,47)(H2,37,38,39,40)/t28-/m0/s1
comment: CX549 is a C-X-C chemokine receptor type 4 (CXCR4) antagonist <Reference id=33759/>, CXCR4 being the receptor for the chemokine CXCL12. CX549 is claimed as compound 63 in patent WO2016048861 <Reference id=33760/>.
iupac name: (2S)-2-amino-5-[4-[[2-[[1-[3-[3-(cyclohexylamino)propylamino]propyl]triazol-4-yl]methylamino]quinazolin-4-yl]amino]piperidin-1-yl]-5-oxopentanoic acid
synonym: compound 63 [WO2016048861]
synonym: CX-549
approved: f
ligand name: CX549
type: SyntheticOrganicLigand

compound 25 [PMID: 28038940]
in ch i key: ORBLOJJZDLUQDF-UHFFFAOYSA-N
in ch i: InChI=1S/C19H19ClN6O3/c1-3-17(27)24-15-6-4-5-7-16(15)29-18-14(20)11-21-19(25-18)23-13-10-22-26(12-13)8-9-28-2/h3-7,10-12H,1,8-9H2,2H3,(H,24,27)(H,21,23,25)
comment: Compound 25 [PMID: 28038940] was developed alongside <Ligand id=9699/>, but is a marginally more potent TAK1 (MAP3K7) inhibitor in biochemical enzyme activity assays than compound 5 <Reference id=33747/>. It has potential anti-inflammatory action, having been shown to normalise induced cytokine secretion from synovial fibroblasts isolated from a patient with rheumatoid arthritis <Reference id=33747/>.
iupac name: N-{2-[(5-chloro-2-{[1-(2-methoxyethyl)-1H-pyrazol-4-yl]amino}pyrimidin-4-yl)oxy]phenyl}prop-2-enamide
approved: f
ligand name: compound 25 [PMID: 28038940]
type: SyntheticOrganicLigand

compound 5 [PMID: 28038940]
in ch i key: SCMLGVPMSXTUNC-UHFFFAOYSA-N
in ch i: InChI=1S/C24H26ClN7O/c1-3-22(33)28-20-6-4-5-7-21(20)29-23-19(25)16-26-24(30-23)27-17-8-10-18(11-9-17)32-14-12-31(2)13-15-32/h3-11,16H,1,12-15H2,2H3,(H,28,33)(H2,26,27,29,30)
comment: Compound 5 [PMID: 28038940] is a covalent inhibitor of TAK1 kinase (MAP3K7) <Reference id=33747/>. It was developed for its potential anti-proliferative activity in cells transformed by the KRAS oncogene.
iupac name: N-{2-[(5-chloro-2-{[4-(4-methylpiperazin-1-yl)phenyl]amino}pyrimidin-4-yl)amino]phenyl}prop-2-enamide
approved: f
ligand name: compound 5 [PMID: 28038940]
type: SyntheticOrganicLigand

GW766994
in ch i key: GPLUUMAKBFSDIE-QGZVFWFLSA-N
comment: GW766994 is an investigational CCR3 antagonist <Reference id=33684/>.
xref: CHEMBL2178574
synonym: GSK766994
synonym: GSK-766994
synonym: GW-766994
approved: f
ligand name: GW766994
type: SyntheticOrganicLigand

CEP-37440
in ch i key: BCSHRERPHLTPEE-NRFANRHFSA-N
in ch i: InChI=1S/C30H38ClN7O3/c1-32-29(40)23-7-3-4-9-25(23)34-28-24(31)19-33-30(36-28)35-26-11-10-20-18-21(6-5-8-22(20)27(26)41-2)38-14-12-37(13-15-38)16-17-39/h3-4,7,9-11,19,21,39H,5-6,8,12-18H2,1-2H3,(H,32,40)(H2,33,34,35,36)/t21-/m0/s1
comment: CEP-37440 is an orally available, dual focal adhesion kinase (FAK) and anaplastic lymphoma kinase (ALK) inhibitor <Reference id=33746/>. The chemical structure is claimed in patent US20170369451 <Reference id=34221/>. The compound is an oncology lead candidate <Reference id=34222/>. Note that this entry has been updated to reflect an error in the article that initially attributed this chemical structure to the compound BMS-986165 (online corrected article <Reference id=33739/>, erratum described in <Reference id=34224/>). The structure of BMS-986165 has not in fact been disclosed.
iupac name: 2-[[5-chloro-2-[[(6S)-6-[4-(2-hydroxyethyl)piperazin-1-yl]-1-methoxy-6,7,8,9-tetrahydro-5H-benzo[7]annulen-2-yl]amino]pyrimidin-4-yl]amino]-N-methylbenzamide
synonym: compound 27b [PMID: 27527804]
synonym: CEP37440
approved: f
ligand name: CEP-37440
type: SyntheticOrganicLigand

solcitinib
in ch i key: MPYACSQFXVMWNO-UHFFFAOYSA-N
in ch i: InChI=1S/C22H23N5O2/c1-22(2)12-26(13-22)20(29)16-10-6-14(7-11-16)17-4-3-5-18-23-21(25-27(17)18)24-19(28)15-8-9-15/h3-7,10-11,15H,8-9,12-13H2,1-2H3,(H,24,25,28)
comment: Solcitinib is a Janus kinase 1 (JAK1)-selective inhibitor, with anti-inflammatory activity <Reference id=33745/>.
iupac name: N-[5-[4-(3,3-dimethylazetidine-1-carbonyl)phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-yl]cyclopropanecarboxamide
xref: CHEMBL3301606
synonym: GLPG-0778
synonym: GLPG0778
synonym: GSK2586184
synonym: compound 1 [WO2010149771]
approved: f
ligand name: solcitinib
type: SyntheticOrganicLigand

oclacitinib
in ch i key: HJWLJNBZVZDLAQ-HAQNSBGRSA-N
in ch i: InChI=1S/C15H23N5O2S/c1-16-23(21,22)9-11-3-5-12(6-4-11)20(2)15-13-7-8-17-14(13)18-10-19-15/h7-8,10-12,16H,3-6,9H2,1-2H3,(H,17,18,19)/t11-,12-
comment: Oclacitinib is an oral pan-Janus kinase (JAK) inhibitor. It is approved as a veterinary drug for treating nonspecific allergic dermatitis and atopic dermatitis in dogs <Reference id=33742/>. We drew the structure as depicted in the WHO INN record for oclacitinib. SMILES generated from the INN structure resolve to PubChem CID 44631938 through structure match, but note that this CID is a tautomer/isomer without specified stereochemistry. The oclacitinib structure also resolves to example 1A claimed in patent WO2010020905, in which the possibility of cis/trans isomers is noted <Reference id=33741/>. Administered as oclacitinib maleate (PF-03394197-11, PubChem CID 44631937).
xref: CHEMBL2103874
synonym: Apoquel® (veterinary use)
synonym: PF-03394197
approved: f
ligand name: oclacitinib
type: SyntheticOrganicLigand

atovaquone
in ch i key: KUCQYCKVKVOKAY-CTYIDZIISA-N
in ch i: InChI=1S/C22H19ClO3/c23-16-11-9-14(10-12-16)13-5-7-15(8-6-13)19-20(24)17-3-1-2-4-18(17)21(25)22(19)26/h1-4,9-13,15,26H,5-8H2/t13-,15-
comment: Atovaquone is a synthetic hydroxynaphthoquinone with broad-spectrum antiprotozoal activity. It is an antimalarial drug and used in combination with <Ligand id=9676/>. Note that we have drawn the molecule as specified by the INN record and ChEMBL entry listed on this summary page. The structure for PubChem CID 74989 (link in table below) is shown without specified stereochemistry (InChi Key BSJMWHQBCZFXBR-UHFFFAOYSA-N).
iupac name: trans-2-[4-(4-Chlorophenyl)cyclohexyl]-3-hydroxy-1,4-naphthalenedione
xref: CHEMBL1450
synonym: Mepron®
synonym: 566C80
synonym: Wellvone®
approved: t
ligand name: atovaquone
type: SyntheticOrganicLigand

LY2389575
canonical SMILES: Clc1ccc(c(c1)Cl)CNC1CCN(C1)c1ncc(cn1)Br
in ch i key: PXQNLQLMRMROSB-ZDUSSCGKSA-N
comment: LY2389575 is a negative allosteric modulator (NAM) that is selective for the metabotropic glutamate receptor 3 <Reference id=21113/>. May be used experimentally as the hydrochloride salt.
iupac name: (3S)-1-(5-bromopyrimidin-2-yl)-N-[(2,4-dichlorophenyl)methyl]pyrrolidin-3-amine
xref: CHEMBL2204436
synonym: LY-2389575
synonym: LY 2389575
approved: f
ligand name: LY2389575
type: SyntheticOrganicLigand

BAY 61-3606
in ch i key: JWQOJVOKBAAAAR-UHFFFAOYSA-N
in ch i: InChI=1S/C20H18N6O3/c1-28-15-6-5-12(10-16(15)29-2)14-11-17-22-8-9-26(17)20(24-14)25-19-13(18(21)27)4-3-7-23-19/h3-11H,1-2H3,(H2,21,27)(H,23,24,25)
comment: BAY 61-3606 is an orally active multi-kinase inhibitor. Inhibitory activity against spleen tyrosine kinase (Syk) <Reference id=33719/> and IKKα <Reference id=33720/> has been demonstrated
xref: CHEMBL1190711
synonym: BAY-613606
synonym: BAY61-3606
synonym: BAY-61-3606
synonym: Syk inhibitor IV
approved: f
ligand name: BAY 61-3606
type: SyntheticOrganicLigand

KBP-7018
isomeric SMILES: COC(=O)c1ccc2c(c1)NC(=O)/C/2=C(/c1ccccc1)/Nc1ccc2c(c1)CCN2C(=O)CN1CCOCC1
in ch i key: JVDJHTYIWQIOCA-ZIADKAODSA-N
in ch i: InChI=1S/C31H30N4O5/c1-39-31(38)22-7-9-24-25(18-22)33-30(37)28(24)29(20-5-3-2-4-6-20)32-23-8-10-26-21(17-23)11-12-35(26)27(36)19-34-13-15-40-16-14-34/h2-10,17-18,32H,11-16,19H2,1H3,(H,33,37)/b29-28-
comment: KBP-7018 is a multikinase inhibitor that simultaneously targets angiogenesis and fibrosis pathways <Reference id=33704/>. It is considered a lead compound for potential therapeutic intervention in idiopathic pulmonary fibrosis. The principal molecular targets of KBP-7018 are the c-KIT, RET and PDGFR tyrosine kinases.
iupac name: methyl (3Z)-3-[[[1-(2-morpholin-4-ylacetyl)-2,3-dihydroindol-5-yl]amino]-phenylmethylidene]-2-oxo-1H-indole-6-carboxylate
synonym: compound 3 [Huang et al., 2017]
approved: f
ligand name: KBP-7018
type: SyntheticOrganicLigand

compound 12p [Larson et al., 2017]
canonical SMILES: NCCn1c(CCCC)nc2c1c1ccc(cc1nc2N)C(=O)OC
isomeric SMILES: NCCn1c(CCCC)nc2c1c1ccc(cc1nc2N)C(=O)OC
in ch i key: ZYCFMHCDZSVIGF-UHFFFAOYSA-N
in ch i: InChI=1S/C18H23N5O2/c1-3-4-5-14-22-15-16(23(14)9-8-19)12-7-6-11(18(24)25-2)10-13(12)21-17(15)20/h6-7,10H,3-5,8-9,19H2,1-2H3,(H2,20,21)
comment: Compound 12p is a selective agonist of Toll-like receptor 8 (TLR8) <Reference id=33703/>.
iupac name: methyl 4-amino-1-(2-aminoethyl)-2-butylimidazo[4,5-c]quinoline-7-carboxylate
approved: f
ligand name: compound 12p [Larson et al., 2017]
type: SyntheticOrganicLigand

MK-0429
in ch i key: HGFOOLONGOBCMP-IBGZPJMESA-N
in ch i: InChI=1S/C23H29N5O4/c1-32-20-9-7-17(15-25-20)19(14-21(29)30)28-13-12-27(23(28)31)11-3-5-18-8-6-16-4-2-10-24-22(16)26-18/h6-9,15,19H,2-5,10-14H2,1H3,(H,24,26)(H,29,30)/t19-/m0/s1
comment: MK-0429 is an orally active, non-peptide inhibitor/antagonist of αv integrins <Reference id=33699/><Reference id=33700/><Reference id=33701/>. It was initially identified as a clinical lead with potential utility for the prevention and treatment of osteoporosis <Reference id=33701/>, but has since shown activity in other biological settings. MK-0429 binds to the αv's Arg-Gly-Asp (RGD)-motif binding domain (the RGD-motif is a conserved sequence in proteins that bind to αv integrins), thereby preventing interaction with RGD-containing binding partners such as osteopontin, bone sialoprotein, vitronectin, and fibrinogen.
iupac name: (3S)-3-(6-methoxypyridin-3-yl)-3-[2-oxo-3-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]imidazolidin-1-yl]propanoic acid
xref: CHEMBL145085
synonym: MK-429
synonym: compound 6 [PMID:14561098]
synonym: MK0429
approved: f
ligand name: MK-0429
type: SyntheticOrganicLigand

maleic acid
canonical SMILES: OC(=O)C=CC(=O)O
isomeric SMILES: OC(=O)/C=C/C(=O)O
in ch i key: VZCYOOQTPOCHFL-UPHRSURJSA-N
in ch i: InChI=1S/C4H4O4/c5-3(6)1-2-4(7)8/h1-2H,(H,5,6)(H,7,8)/b2-1-
comment: Maleic acid or cis-butenedioic acid is an organic compound that is a dicarboxylic acid, a molecule with two carboxyl groups.
iupac name: (2Z)-But-2-enedioic acid
approved: f
ligand name: maleic acid
type: SyntheticOrganicLigand

RIPK2 inhibitor 8
in ch i key: QWDMZDSZMVJFFJ-UHFFFAOYSA-N
in ch i: InChI=1S/C18H21FN4O3S/c1-5-26-13-8-17-21-9-12(11-6-15(19)22-16(20)7-11)23(17)10-14(13)27(24,25)18(2,3)4/h6-10H,5H2,1-4H3,(H2,20,22)
comment: This compound 8 is a potent, selective and orally bioavailable RIPK2 inhibitor, that is suitable as an experimental tool to examine the effects of inhibition of RIPK2 in in vitro and in vivo experiments <Reference id=33698/>.
iupac name: 4-[7-ethoxy-6-(2-methylpropane-2-sulfonyl)imidazo[1,2-a]pyridin-3-yl]-6-fluoropyridin-2-amine
approved: f
ligand name: RIPK2 inhibitor 8
type: SyntheticOrganicLigand

GI254023X
in ch i key: GHVMTHKJUAOZJP-CGTJXYLNSA-N
in ch i: InChI=1S/C21H33N3O4/c1-15(24(28)14-25)17(13-9-12-16-10-7-6-8-11-16)19(26)23-18(20(27)22-5)21(2,3)4/h6-8,10-11,14-15,17-18,28H,9,12-13H2,1-5H3,(H,22,27)(H,23,26)/t15-,17+,18+/m0/s1
comment: GI254023X is an ADAM10-selective inhibitor <Reference id=33695/>. It can be used as a pharmacological tool to interrogate the relevance of ADAM10 sheddase activity in biological assays.
iupac name: (2R)-N-[(1S)-2,2-Dimethyl-1-[(methylamino)carbonyl]propyl]-2-[(1S)-1-(N-hydroxyformamido)ethyl]-5-phenylpentanamide
xref: CHEMBL1229516
synonym: GI 254023X
synonym: GI-254023X
approved: f
ligand name: GI254023X
type: SyntheticOrganicLigand

tapinarof
canonical SMILES: CC(c1c(O)cc(cc1O)C=Cc1ccccc1)C
isomeric SMILES: CC(c1c(O)cc(cc1O)/C=C/c1ccccc1)C
in ch i key: ZISJNXNHJRQYJO-CMDGGOBGSA-N
in ch i: InChI=1S/C17H18O2/c1-12(2)17-15(18)10-14(11-16(17)19)9-8-13-6-4-3-5-7-13/h3-12,18-19H,1-2H3/b9-8+
comment: Tapinarof (GSK2894512) is an aryl hydrocarbon receptor (AhR) agonist <Reference id=33691/>. It is a naturally occurring polyphenol derived from bacteria that exist symbiotically with entomopathogenic nematodes. AhR was identified as the primary molecular target based on phenotypic screening using the DiscoveRx BioMAP Diversity Plus System and confirmed using AhR knockout mice. Tapinarof was the first steroid-free topical drug in this class to be approved as a plaque psoriasis medication.
iupac name: 5-[(E)-2-phenylethenyl]-2-propan-2-ylbenzene-1,3-diol
xref: CHEMBL259571
synonym: WBI 1001
synonym: WBI-1001
synonym: GSK2894512
synonym: WB-1001
synonym: GSK-2894512
synonym: Vtama®
approved: t
ligand name: tapinarof
type: SyntheticOrganicLigand

compound 12a [PMID: 29031075]
in ch i key: MITGKKFYIJJQGL-UHFFFAOYSA-N
in ch i: InChI=1S/C20H16ClNO4S/c1-27(25,26)14-9-10-16-15(11-14)19-17(3-2-4-18(19)23)22(16)20(24)12-5-7-13(21)8-6-12/h5-11H,2-4H2,1H3
comment: Compound 12a [PMID: 29031075] is an <Ligand id=1909/> analogue that was rationally designed in order to optimise COX-2 selectivity <Reference id=33686/>. Compound 12a has comparable in vitro COX-2 inhibitory activity to indomethacin and <Ligand id=2892/>, but has improved selectivity for COX-2 compared to celecoxib (330-fold selectivity in this study <Reference id=33686/>). In contrast, it is > 450-fold selective for COX-2 over COX-1.
iupac name: 9-(4-chlorobenzoyl)-6-methanesulfonyl-2,3,4,9-tetrahydro-1H-carbazol-4-one
approved: f
ligand name: compound 12a [PMID: 29031075]
type: SyntheticOrganicLigand

compound 3v [PMID: 27390066]
canonical SMILES: COc1ccc(cc1)CCNCC(P(=O)(O)O)N
isomeric SMILES: COc1ccc(cc1)CCNCC(P(=O)(O)O)N
in ch i key: HFIVLLBFACNAFN-UHFFFAOYSA-N
in ch i: InChI=1S/C11H19N2O4P/c1-17-10-4-2-9(3-5-10)6-7-13-8-11(12)18(14,15)16/h2-5,11,13H,6-8,12H2,1H3,(H2,14,15,16)
comment: Compound 3v [PMID: 27390066] is an inhibitor of the human endoplasmic reticulum aminopeptidase ERAP2, with ~400-fold selectivity over ERAP1 <Reference id=33685/>. It is suitable as a tool compound for elucidating the role of ERAP2 vs. ERAP1 in antigen processing and in human diseases. Its action can be compared with that of the non-selective <Ligand id=9682/>.
iupac name: [1-amino-2-[2-(4-methoxyphenyl)ethylamino]ethyl]phosphonic acid
xref: CHEMBL3806197
approved: f
ligand name: compound 3v [PMID: 27390066]
type: SyntheticOrganicLigand

compound 2g [PMID: 27390066]
canonical SMILES: OC(=O)C(CP(=O)(C(CCc1ccc(cc1)[N+](=O)[O-])N)O)Cc1ccccc1
isomeric SMILES: OC(=O)C(CP(=O)(C(CCc1ccc(cc1)[N+](=O)[O-])N)O)Cc1ccccc1
in ch i key: YSYQXQQIKOEBNN-UHFFFAOYSA-N
in ch i: InChI=1S/C19H23N2O6P/c20-18(11-8-14-6-9-17(10-7-14)21(24)25)28(26,27)13-16(19(22)23)12-15-4-2-1-3-5-15/h1-7,9-10,16,18H,8,11-13,20H2,(H,22,23)(H,26,27)
comment: Compound 2g [PMID: 27390066] is a non-selective inhibitor of the human endoplasmic reticulum aminopeptidases ERAP1 and ERAP2 <Reference id=33685/>. The action of this compound can be compared with that of the ERAP2-selective <Ligand id=9683/>.
iupac name: 2-[[[1-amino-3-(4-nitrophenyl)propyl]-hydroxyphosphoryl]methyl]-3-phenylpropanoic acid
xref: CHEMBL3355101
approved: f
ligand name: compound 2g [PMID: 27390066]
type: SyntheticOrganicLigand

compound 13c [PMID: 20684591]
in ch i key: DIZACSOTRSXCHC-UHFFFAOYSA-N
in ch i: InChI=1S/C23H28N6/c1-2-4-19(5-3-1)27-22-15-17(6-9-26-22)21-14-18-16-25-8-7-20(18)23(28-21)29-12-10-24-11-13-29/h6-9,14-16,19,24H,1-5,10-13H2,(H,26,27)
comment: Compound 13c [PMID: 20684591] is a potent, orally active and competitive inhibitor of all three isoforms of protein kinase D <Reference id=33681/>. It is one of the chemical structures claimed in Novartis' patent WO2008122615 <Reference id=33682/>.
iupac name: N-cyclohexyl-4-(1-piperazin-1-yl-2,6-naphthyridin-3-yl)pyridin-2-amine
xref: CHEMBL1214998
approved: f
ligand name: compound 13c [PMID: 20684591]
type: SyntheticOrganicLigand

AZD2098
canonical SMILES: COc1nccnc1NS(=O)(=O)c1cccc(c1Cl)Cl
isomeric SMILES: COc1nccnc1NS(=O)(=O)c1cccc(c1Cl)Cl
in ch i key: FLSMVCMSUNISFK-UHFFFAOYSA-N
comment: AZD2098 is a potent and bioavailable aminopyrazine sulfonamide CCR4 receptor antagonist discovered in a high-throughput screening/synthesis campaign <Reference id=33675/>.
iupac name: 2,3-dichloro-N-(3-methoxypyrazin-2-yl)benzenesulfonamide
synonym: AZD-2098
synonym: compound 47 [PMID: 28947948]
approved: f
ligand name: AZD2098
type: SyntheticOrganicLigand

cibinetide
in ch i key: WZTIQQBMSJTRBR-WYKNNRPVSA-N
in ch i: InChI=1S/C51H84N16O21/c1-22(2)17-30(47(84)65-32(19-36(53)71)48(85)66-33(20-68)49(86)67-34(21-69)50(87)88)63-40(77)24(5)57-41(78)25(7-6-16-56-51(54)55)59-43(80)29(11-15-39(75)76)62-46(83)31(18-23(3)4)64-45(82)27(8-12-35(52)70)60-44(81)28(10-14-38(73)74)61-42(79)26-9-13-37(72)58-26/h22-34,68-69H,6-21H2,1-5H3,(H2,52,70)(H2,53,71)(H,57,78)(H,58,72)(H,59,80)(H,60,81)(H,61,79)(H,62,83)(H,63,77)(H,64,82)(H,65,84)(H,66,85)(H,67,86)(H,73,74)(H,75,76)(H,87,88)(H4,54,55,56)/t24-,25-,26-,27-,28-,29-,30-,31-,32-,33-,34-/m0/s1
comment: Cibinetide (ARA 290) is an engineered peptide that mimics the 3 dimensional structure of the helix B surface domain of erythropoietin (EPO). It is designed to bind selectively to the non-hematopoietic EPO receptor (sometimes referred to as the innate repair receptor or IRR), that is believed to be a heterodimer of EPOR and the cytokine family beta common receptor (βCR, CD131) <Reference id=33651/><Reference id=33660/>. Non-hematopoietic EPO ligands have potential tissue protective and anti-inflammatory actions <Reference id=33652/><Reference id=33653/><Reference id=33654/><Reference id=33655/><Reference id=33656/><Reference id=33658/>. The IRR is suggested to be a point of integration between the immune system and pain signalling (via nociception) <Reference id=33657/>. Cibinetide is SEQ ID NO. 282 (and peptide ID) as claimed in patent WO2009094172 <Reference id=33662/>.
iupac name: (4S)-5-[[(2S)-5-amino-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-4-amino-1-[[(2S)-1-[[(1S)-1-carboxy-2-hydroxyethyl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-1,4-dioxobutan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-1-oxopropan-2-yl]amino]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]amino]-4-carboxy-1-oxobutan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-1,5-dioxopentan-2-yl]amino]-5-oxo-4-[[(2S)-5-oxopyrrolidine-2-carbonyl]amino]pentanoic acid
xref: CHEMBL3545305
synonym: ARA 290
synonym: ARA290
synonym: ARA-290
synonym: PHBSP
synonym: PH-BSP
approved: f
ligand name: cibinetide
type: PeptideLigand

proguanil
canonical SMILES: CC(N=C(/N=C(/Nc1ccc(cc1)Cl)/N)N)C
isomeric SMILES: CC(N=C(/N=C(/Nc1ccc(cc1)Cl)/N)N)C
in ch i key: SSOLNOMRVKKSON-UHFFFAOYSA-N
in ch i: InChI=1S/C11H16ClN5/c1-7(2)15-10(13)17-11(14)16-9-5-3-8(12)4-6-9/h3-7H,1-2H3,(H5,13,14,15,16,17)
comment: Proguanil is a biguanide derivative that, once administered, is converted to the active metabolite <Ligand id=10027/>. It is an antimalarial drug, used in combination with <Ligand id=9695/> or with <Ligand id=5535/>. The marketed formulations contain proguanil hydrochloride (PubChem CID 9570076).
iupac name: (1E)-1-[amino-(4-chloroanilino)methylidene]-2-propan-2-ylguanidine
xref: CHEMBL1377
synonym: Paludrine®
synonym: chloroguanide
synonym: Bigumal®
synonym: chlorguanide
approved: t
ligand name: proguanil
type: SyntheticOrganicLigand

andrographolide
in ch i key: BOJKULTULYSRAS-OTESTREVSA-N
in ch i: InChI=1S/C20H30O5/c1-12-4-7-16-19(2,9-8-17(23)20(16,3)11-21)14(12)6-5-13-15(22)10-25-18(13)24/h5,14-17,21-23H,1,4,6-11H2,2-3H3/b13-5+/t14-,15-,16+,17-,19+,20+/m1/s1
comment: Andrographolide is a major component of the leaves of the traditionally used medicinal plant Andrographis paniculata (Acanthaceae) <Reference id=33629/>. Andrographolide and analogues are being investigated for their potential anti-inflammatory activities <Reference id=33628/>, but andrographolide has also shown anti-viral, anti-thrombotic, hepatoprotective and anti-cancer properties <Reference id=33629/>. Accumulated evidence indicates that the principal mechanism undelying andrographolide's anti-inflammatory action is inhibition of NF-κB. Additional studies show that Nrf2 activation by andrographolide likely enhances endogenous antioxidant defense mechanisms. Direct covalent interaction with Cys62, and non-covalent binding are both required for andrographolide-induced inhibition of NF-κB p50 <Reference id=33630/>.
iupac name: (3E,4S)-3-[2-[(1R,4aS,5R,6R,8aS)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]ethylidene]-4-hydroxyoxolan-2-one
approved: f
ligand name: andrographolide
type: SyntheticOrganicLigand

compound 1 [PMID: 28611375]
in ch i key: QTYHUADZOPIUME-UHFFFAOYSA-N
comment: Compound 1 is reported as a direct inhibitor of the protein-protein interaction between TNFα and both of its receptors (TNFRI and TNFRII) <Reference id=33619/>. The compound is orally active, which is in contrast to the TNFα biologics that are already in clinical use e.g. <Ligand id=5004/>, <Ligand id=4860/> and <Ligand id=6789/>. Compound 1 interacts with TNFα in a two-site binding mode with a high affinity site (nM) and a low affinity site (μM) detected <Reference id=33619/>. This mechanism interferes with TNFα homotrimer (bioactive cytokine) formation, and thereby inhibits TNF receptor activation. The physicochemical properties of compound 1 are not optimal (especially wrt solubility), so some medicinal chemistry effort would need to be applied to create a more efficient drug-like molecule.
iupac name: N-(3-chloro-2-methylphenyl)-N-[2-oxo-2-[4-(phenylmethyl)piperazin-1-yl]ethyl]benzenesulfonamide
approved: f
ligand name: compound 1 [PMID: 28611375]
type: SyntheticOrganicLigand

FX1
isomeric SMILES: OC(=O)CCN1C(=S)S/C(=C/2/C(=O)NC3C2C=C(Cl)C=C3)/C1=O
in ch i key: NLLDCQPHRJHMSX-KHPPLWFESA-N
comment: FX1 is a potent and selective BCL6 inhibitor rationally designed to target BCL6-driven diffuse large B cell lymphoma <Reference id=33617/>. FX1 inhibits binding of BCL6 corepressor proteins and formation of functional repression complexes at its endogenous target genes (BCL6 target genes include CD69, CXCR4, and CDKN1A loci).
iupac name: 3-{5-[(3Z)-5-chloro-2-oxo-2,3,3a,7a-tetrahydro-1H-indol-3-ylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl}propanoic acid
approved: f
ligand name: FX1
type: SyntheticOrganicLigand

PFK15
canonical SMILES: O=C(c1ccncc1)C=Cc1ccc2c(n1)cccc2
isomeric SMILES: O=C(c1ccncc1)C=Cc1ccc2c(n1)cccc2
in ch i key: UJJUKZPBUMCSJZ-UHFFFAOYSA-N
in ch i: InChI=1S/C17H12N2O/c20-17(14-9-11-18-12-10-14)8-7-15-6-5-13-3-1-2-4-16(13)19-15/h1-12H
comment: PFK15 is a small molecule inhibitor of the metabolic sugar phosphatase PFKFB3 initially investigated for anti-cancer effects <Reference id=33060/>, and more recently predicted to be of clinical benefit in the management of joint destruction in rheumatoid arthritis <Reference id=33058/>.
iupac name: 1-(pyridin-4-yl)-3-(quinolin-2-yl)prop-2-en-1-one
xref: CHEMBL3105836
synonym: PFK-015
approved: f
ligand name: PFK15
type: SyntheticOrganicLigand

compound 8c [PMID: 28760529]
in ch i key: RRELDGDKULRRDM-UHFFFAOYSA-N
in ch i: InChI=1S/C20H20ClN3O5/c21-15-10-18(24(26)27)19(29-14-5-7-28-8-6-14)11-17(15)22-13-2-3-16-12(9-13)1-4-20(25)23-16/h2-3,9-11,14,22H,1,4-8H2,(H,23,25)
comment: 8c is a potent B-cell lymphoma 6 (BCL6)-corepressor interaction inhibitor with a favourable pharmacokinetic profile for drug development <Reference id=33616/>.
iupac name: 6-{[2-chloro-4-nitro-5-(oxan-4-yloxy)phenyl]amino}-3,4-dihydro-1H-quinolin-2-one
approved: f
ligand name: compound 8c [PMID: 28760529]
type: SyntheticOrganicLigand

compound 28 [PMID: 28671460]
canonical SMILES: COc1ccc2c(c1)nc(nc2C)N=C(N)N
isomeric SMILES: COc1ccc2c(c1)nc(nc2C)N=C(N)N
in ch i key: ZJBMSSBTCGJZEE-UHFFFAOYSA-N
in ch i: InChI=1S/C11H13N5O/c1-6-8-4-3-7(17-2)5-9(8)15-11(14-6)16-10(12)13/h3-5H,1-2H3,(H4,12,13,14,15,16)
comment: A virtual screening study to identify myeloperoxidase (MPO) inhibitors discovered compound 28 as the most potent from a library of 727842 compounds <Reference id=33611/>. Compound 28 is an irreversible, mechanism-based inhibitor.
iupac name: 2-(7-methoxy-4-methylquinazolin-2-yl)guanidine
xref: CHEMBL581893
approved: f
ligand name: compound 28 [PMID: 28671460]
type: SyntheticOrganicLigand

BTB07018
in ch i key: FPHDAMLVFFWTQL-UHFFFAOYSA-N
comment: BTB07018 is a non-competitive inhibitor of aminopeptidase N <Reference id=33608/>. It was discovered in the same virtual screening study as <Ligand id=9668/>.
approved: f
ligand name: BTB07018
type: SyntheticOrganicLigand

JFD00064
in ch i key: IXJJCXATJSXNJM-UHFFFAOYSA-N
in ch i: InChI=1S/C31H18N2/c32-18-24-16-20(17-30-26-8-4-2-6-22(26)9-12-27(24)30)15-23-11-14-28-25-7-3-1-5-21(25)10-13-29(28)31(23)19-33/h1-14,16-17H,15H2
comment: JFD00064 is a non-peptidic inhibitor of aminopeptidase N (APN) <Reference id=33608/>. Unlike other APN inhibitors it is non-competitive with respect to the enzyme's zinc binding domain.
iupac name: 2-[(1-cyanophenanthren-3-yl)methyl]phenanthrene-1-carbonitrile
approved: f
ligand name: JFD00064
type: SyntheticOrganicLigand

zimlovisertib
in ch i key: JKDGKIBAOAFRPJ-ZBINZKHDSA-N
in ch i: InChI=1S/C18H20FN3O4/c1-3-10-13(22-17(24)15(10)19)8-26-18-11-7-14(25-2)12(16(20)23)6-9(11)4-5-21-18/h4-7,10,13,15H,3,8H2,1-2H3,(H2,20,23)(H,22,24)/t10-,13+,15-/m0/s1
comment: PF-06650833 is a small molecule, reversible, potent and selective IRAK4 inhibitor identified as a clinical lead <Reference id=33587/>. Its pharmacokinetic profile suggests it will be orally bioavailable. Structurally it is an analogue of <Ligand id=9666/>. The chemical structure for the INN zimlovisertib is identical to the structure of PF-06650833.
synonym: compound 40 [PMID: 28498658]
synonym: PF06650833
synonym: PF-06650833
approved: f
ligand name: zimlovisertib
type: SyntheticOrganicLigand

PF-06426779
in ch i key: GISRWBROCYNDME-PELMWDNLSA-N
in ch i: InChI=1S/C17H18FN3O4/c1-8-12(21-16(23)14(8)18)7-25-17-10-6-13(24-2)11(15(19)22)5-9(10)3-4-20-17/h3-6,8,12,14H,7H2,1-2H3,(H2,19,22)(H,21,23)/t8-,12+,14-/m0/s1
comment: PF-06426779 is an IRAK4 inhibitor. It is claimed as example 189 in Pfizer's patent WO2015150995 <Reference id=33586/>.
iupac name: 1-{[(2S,3S,4S)-4-fluoro-3-methyl-5-oxopyrrolidin-2-yl]methoxy}-7-methoxyisoquinoline-6-carboxamide
synonym: example 189 [WO2015150995]
synonym: example 38 [PMID:28498658]
approved: f
ligand name: PF-06426779
type: SyntheticOrganicLigand

BML-281
in ch i key: WWGBHDIHIVGYLZ-UHFFFAOYSA-N
in ch i: InChI=1S/C22H30N4O6/c1-22(2,3)31-21(29)24-16-11-9-15(10-12-16)18-14-17(26-32-18)20(28)23-13-7-5-4-6-8-19(27)25-30/h9-12,14,30H,4-8,13H2,1-3H3,(H,23,28)(H,24,29)(H,25,27)
comment: BML-281 is an experimental selective HDAC6/3 inhibitor <Reference id=33573/>, that has demonstrated anti-inflammatory activity in a murine model of colonic inflammation <Reference id=33574/>.
iupac name: tert-butyl N-[4-[3-[[7-(hydroxyamino)-7-oxoheptyl]carbamoyl]-1,2-oxazol-5-yl]phenyl]carbamate
xref: CHEMBL511749
synonym: compound 3 [PMID: 18642892]
approved: f
ligand name: BML-281
type: SyntheticOrganicLigand

KA1010
canonical SMILES: ONC(=O)CCCCCCN(c1ccccn1)c1ccccn1
isomeric SMILES: ONC(=O)CCCCCCN(c1ccccn1)c1ccccn1
in ch i key: QKTORDWLHYWRJF-UHFFFAOYSA-N
in ch i: InChI=1S/C17H22N4O2/c22-17(20-23)11-3-1-2-8-14-21(15-9-4-6-12-18-15)16-10-5-7-13-19-16/h4-7,9-10,12-13,23H,1-3,8,11,14H2,(H,20,22)
comment: KA1010 is a selective HDAC6 inhibitor that acts as an immunosuppressant <Reference id=33566/>. It was used as a tool to define the role of HDAC6 in the the human alloimmune response, and identified HDAC6 as a drug target with potential use in transplantation.
iupac name: 7-(dipyridin-2-ylamino)-N-hydroxyheptanamide
xref: CHEMBL3675757
approved: f
ligand name: KA1010
type: SyntheticOrganicLigand

pyrotinib
in ch i key: SADXACCFNXBCFY-IYNHSRRRSA-N
in ch i: InChI=1S/C32H31ClN6O3/c1-3-41-30-17-27-25(16-28(30)38-31(40)12-10-24-8-6-14-39(24)2)32(21(18-34)19-36-27)37-22-9-11-29(26(33)15-22)42-20-23-7-4-5-13-35-23/h4-5,7,9-13,15-17,19,24H,3,6,8,14,20H2,1-2H3,(H,36,37)(H,38,40)/b12-10+/t24-/m1/s1
comment: Pyrotinib (SHR1258) is an orally administered, irreversible inhibitor of the tyrosine kinase activities of the EGFR (HER1), HER2 and HER4 <Reference id=33558/><Reference id=33559/>. It is claimed as example 5 in patent US20120165352 <Reference id=33560/>.
iupac name: (E)-N-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]-3-cyano-7-ethoxyquinolin-6-yl]-3-[(2R)-1-methylpyrrolidin-2-yl]prop-2-enamide
xref: CHEMBL3647420
synonym: SHR1258
synonym: SHR-1258
synonym: SHR 1258
synonym: compound 12 [PMID: 28115222]
synonym: Airuini®
approved: t
ligand name: pyrotinib
type: SyntheticOrganicLigand

GSK2981278
in ch i key: LZLBRISQTJVZNP-UHFFFAOYSA-N
in ch i: InChI=1S/C25H35NO5S/c1-4-20-5-7-23(8-6-20)26(16-19(2)3)32(28,29)24-9-10-25(22(15-24)17-27)31-18-21-11-13-30-14-12-21/h5-10,15,19,21,27H,4,11-14,16-18H2,1-3H3
comment: GSK2981278 is a potent and selective inverse agonist of the nuclear receptor retinoid-related orphan receptor, RORγ <Reference id=33538/>. It has been investigated for anti-inflammatory potential.
iupac name: N-(4-ethylphenyl)-3-(hydroxymethyl)-N-(2-methylpropyl)-4-(oxan-4-ylmethoxy)benzenesulfonamide
approved: f
ligand name: GSK2981278
type: SyntheticOrganicLigand

GNE-3500
in ch i key: WLCIIQPUMOJJOF-MHECFPHRSA-N
in ch i: InChI=1S/C24H30FN3O3S/c1-18-8-11-24(20-6-4-3-5-7-20)32(30,31)28(18)17-21-9-10-22(16-23(21)25)27-14-12-26(13-15-27)19(2)29/h3-7,9-10,16,18,24H,8,11-15,17H2,1-2H3/t18-,24+/m0/s1
comment: GNE-3500 is a potent, selective, and orally bioavailable retinoic acid receptor-related orphan receptor C (RORC or RORγ) inverse agonist, being evaluated for anti-inflammatory potential <Reference id=33537/>.
iupac name: 1-[4-[3-fluoro-4-[[(3S,6R)-3-methyl-1,1-dioxo-6-phenylthiazinan-2-yl]methyl]phenyl]piperazin-1-yl]ethanone
approved: f
ligand name: GNE-3500
type: SyntheticOrganicLigand

PF-04957325
in ch i key: VNLPYEMGHGDRRZ-MRVPVSSYSA-N
in ch i: InChI=1S/C14H15F3N8OS/c15-14(16,17)13-20-11(18)10-12(21-13)25(23-22-10)6-8-5-24(2-3-26-8)7-9-19-1-4-27-9/h1,4,8H,2-3,5-7H2,(H2,18,20,21)/t8-/m1/s1
comment: PF-04957325 is a selective inhibitor of PDE8 <Reference id=33531/> that is a useful chemical probe for studying the biological function of PDE8. It is compound 1-38 in patent WO2016030345 <Reference id=33530/>.
iupac name: 3-[[(2R)-4-(1,3-thiazol-2-ylmethyl)morpholin-2-yl]methyl]-5-(trifluoromethyl)triazolo[4,5-d]pyrimidin-7-amine
approved: f
ligand name: PF-04957325
type: SyntheticOrganicLigand

cevimeline
canonical SMILES: CC1SCC2(O1)CN1CCC2CC1
isomeric SMILES: CC1SCC2(O1)CN1CCC2CC1
in ch i key: WUTYZMFRCNBCHQ-UHFFFAOYSA-N
in ch i: InChI=1S/C10H17NOS/c1-8-12-10(7-13-8)6-11-4-2-9(10)3-5-11/h8-9H,2-7H2,1H3
comment: Cevimeline is an orally administered cholinergic analogue with parasympathomimetic activity. The INN is a mixture of enantiomers. We show the structure without stereochemistry to represent the mixture.
xref: CHEMBL168815
synonym: Evoxac®
approved: t
ligand name: cevimeline
type: SyntheticOrganicLigand

varespladib
in ch i key: BHLXTPHDSZUFHR-UHFFFAOYSA-N
in ch i: InChI=1S/C21H20N2O5/c1-2-14-19(20(26)21(22)27)18-15(9-6-10-16(18)28-12-17(24)25)23(14)11-13-7-4-3-5-8-13/h3-10H,2,11-12H2,1H3,(H2,22,27)(H,24,25)
comment: Varespladib (LY315920) is a secretory phospholipase A2 (sPLA2) inhibitor <Reference id=33512/><Reference id=33510/> in clinical development. The administered form can be varespladib sodium (A-001, for intravenuous administration) or varespladib methyl (A-002, for oral administration). The history of varespladib's discovery and development is summarized in <Reference id=33511/>.
iupac name: 2-(1-benzyl-2-ethyl-3-oxamoylindol-4-yl)oxyacetic acid
xref: CHEMBL148674
synonym: LY315920
synonym: LY-315920
synonym: S-5920
synonym: S 5920
synonym: varespladib methyl (A-002)
synonym: varespladib sodium (A-001)
synonym: compound 6m [PMID: 8978844]
approved: f
ligand name: varespladib
type: SyntheticOrganicLigand

Takinib
isomeric SMILES: CCCn1/c(=N/C(=O)c2cccc(c2)C(=O)N)/[nH]c2c1cccc2
in ch i key: UOZVVPXKJGOFIG-UHFFFAOYSA-N
in ch i: InChI=1S/C18H18N4O2/c1-2-10-22-15-9-4-3-8-14(15)20-18(22)21-17(24)13-7-5-6-12(11-13)16(19)23/h3-9,11H,2,10H2,1H3,(H2,19,23)(H,20,21,24)
comment: Takinib is a potent, ATP-competitive and selective inhibitor of the TAK1 kinase (MAP3K7) <Reference id=33492/>. It is reported to sensitize cells to TNF-α-induced apoptosis, an effect that has potential application in oncology and autoimmune disease treatment.
iupac name: 3-N-(1-propylbenzimidazol-2-yl)benzene-1,3-dicarboxamide
approved: f
ligand name: Takinib
type: SyntheticOrganicLigand

mapracorat
in ch i key: VJGFOYBQOIPQFY-XMMPIXPASA-N
in ch i: InChI=1S/C25H26F4N2O2/c1-15-7-8-18-20(5-4-6-21(18)31-15)30-14-24(32,25(27,28)29)13-23(2,3)19-12-17(26)11-16-9-10-33-22(16)19/h4-8,11-12,30,32H,9-10,13-14H2,1-3H3/t24-/m1/s1
comment: Mapracorat is a novel non-steroidal selective glucocorticoid receptor agonist (SEGRA) <Reference id=33488/><Reference id=33489/>. SEGRAs exert their pharmacological effect by activating only the transrepression pathway, which is in contrast to traditional glucocorticosteroids (GCs) which activate both the transactivation and transrepression pathways.The pharmaceutical industry is trying to develop new GCs that are as effective as traditional GCs, but with fewer limiting adverse effects. Mapracorat and <Ligand id=9653/> are prototype compounds that were designed to address this clinical need.
xref: CHEMBL2103876
synonym: ZK-245186
synonym: BOL-303242-X
synonym: ZK 245186
synonym: ZK245186
approved: f
ligand name: mapracorat
type: SyntheticOrganicLigand

GSK866
in ch i key: LKQMULLPLYLIGW-QFIPXVFZSA-N
comment: GSK866 is a prototype of a class of compounds called selective glucocorticoid receptor agonists (SEGRAs). SEGRAs exert their pharmacological effect by activation of only the transrepression pathway, which is in contrast to traditional glucocorticosteroids which activate both the transactivation and transrepression pathways. Development of SEGRAs is aiming to improve the risk-benefit profile associated with use of traditional glucocorticosteroids drugs. See also our entry for <Ligand id=9654/>, a SEGRA that advanced to clinical trial. GSK866 is example 1 in <Reference id=33484/>, which is shown bound to the glucocortocoid receptor in the X-ray structure 3E7C. A series of novel covalently binding SEGRAs based on the structure of GSK866 is reported in <Reference id=33485/>. Note that there is some ambiguity in the literature and online chemistry resources as to the precise stereochemistry of this ligand. We show the S isomer as specificed by the SMILES string supplied in the PDB entry.
iupac name: 5-amino-N-[(2S)-2-[[(2,6-dichlorobenzoyl)-ethylamino]methyl]-3,3,3-trifluoro-2-hydroxypropyl]-1-(4-fluorophenyl)pyrazole-4-carboxamide
approved: f
ligand name: GSK866
type: SyntheticOrganicLigand

NSC157058
canonical SMILES: Clc1nc2n[nH]nc2nc1Cl
isomeric SMILES: Clc1nc2n[nH]nc2nc1Cl
in ch i key: RKHFIGLWZHVDCG-UHFFFAOYSA-N
in ch i: InChI=1S/C4HCl2N5/c5-1-2(6)8-4-3(7-1)9-11-10-4/h(H,7,8,9,10,11)
comment: NSC157058, the most potent compound reported in this paper <Reference id=33483/>, is a Zikavirus protease inhibitor, possibly binding at the NS2B-NS3 interface. It was also an inhibitor of ZIKV propagation in human fetal neural progenitor cells and in vivo in SJL mice <Reference id=33483/>.
iupac name: 5,6-dichloro-2H-triazolo[4,5-e]pyrazine
approved: f
ligand name: NSC157058
type: SyntheticOrganicLigand

K-8794
in ch i key: MTNFANNLCUMCNB-UHFFFAOYSA-N
in ch i: InChI=1S/C36H38N6O6S/c1-23-11-9-12-24(2)30(23)39-29(43)19-22-47-35-31(48-28-14-8-7-13-27(28)46-6)32(40-34(41-35)33-37-20-10-21-38-33)42-49(44,45)26-17-15-25(16-18-26)36(3,4)5/h7-18,20-21H,19,22H2,1-6H3,(H,39,43)(H,40,41,42)
comment: K-8794 is an orally active selective ETB-receptor antagonist developed by Kowa in Japan. In 2017 it was crystalised in 5XPR with the Endothelin B receptor.
iupac name: 3-[6-[(4-tert-butylphenyl)sulfonylamino]-5-(2-methoxyphenoxy)-2-pyrimidin-2-ylpyrimidin-4-yl]oxy-N-(2,6-dimethylphenyl)propanamide
approved: f
ligand name: K-8794
type: SyntheticOrganicLigand

dagrocorat
in ch i key: QJJBNCHSWFGXML-KEKPKEOLSA-N
in ch i: InChI=1S/C29H29F3N2O2/c1-19-25(8-5-15-33-19)34-26(35)22-10-12-24-21(16-22)9-11-23-18-28(36,29(30,31)32)14-13-27(23,24)17-20-6-3-2-4-7-20/h2-8,10,12,15-16,23,36H,9,11,13-14,17-18H2,1H3,(H,34,35)/t23-,27+,28-/m1/s1
comment: Dagrocorat (PF-00251802) is the active metabolite of prodrug <Ligand id=9649/>. See the ligand page for the prodrug for further details of its development and potential clinical utility.
iupac name: (4bS,7R,8aR)-4b-benzyl-7-hydroxy-N-(2-methylpyridin-3-yl)-7-(trifluoromethyl)-5,6,8,8a,9,10-hexahydrophenanthrene-2-carboxamide
xref: CHEMBL3137304
synonym: PF-00251802
approved: f
ligand name: dagrocorat
type: SyntheticOrganicLigand

fosdagrocorat
in ch i key: BVXLAHSJXXSWFF-KEKPKEOLSA-N
comment: Fosdagrocorat (PF-04171327) is a glucocorticoid (GC) receptor partial agonist with anti-inflammatory potential. It is an example of a new class of GC substances termed dissociated agonists of the GC receptors (DAGR), that are being developed to improve the risk-benefit profile of GC drugs. DAGRs are designed to favour interaction of the GC receptor with protein partners rather than DNA, such that the transrepressive actions are enhanced over the transactivation effects. The hypothesis is that dissociating transrepression from transactivation will cause less undesirable effects on bone and glucose metabolism compared to current GC agonists such as <Ligand id=7096/> (reviewed in <Reference id=33473/>). Fosdagrocorat is example 2 in Pfizer's patent US8901310 <Reference id=33474/>. It is a phosphate ester prodrug of <Ligand id=9650/> (example 1 in US8901310). Synthesis and structure-activity relationship (SAR) of another series of DAGRs (by Boehringer Ingelheim Pharmaceuticals) are reported in <Reference id=33475/>.
iupac name: [(2R,4aS,10aR)-4a-benzyl-7-[(2-methylpyridin-3-yl)carbamoyl]-2-(trifluoromethyl)-1,3,4,9,10,10a-hexahydrophenanthren-2-yl] dihydrogen phosphate
xref: CHEMBL3137316
synonym: PF-04171327
approved: f
ligand name: fosdagrocorat
type: SyntheticOrganicLigand

BRD3444
canonical SMILES: OCC1N2CCCCN(CC2C1c1ccc(cc1)C#Cc1ccccc1)C(=O)Nc1ccc(cc1)OC
in ch i key: OJOYTIQMDFICSJ-FRXPANAUSA-N
in ch i: InChI=1S/C31H33N3O3/c1-37-27-17-15-26(16-18-27)32-31(36)33-19-5-6-20-34-28(21-33)30(29(34)22-35)25-13-11-24(12-14-25)10-9-23-7-3-2-4-8-23/h2-4,7-8,11-18,28-30,35H,5-6,19-22H2,1H3,(H,32,36)/t28-,29+,30+/m0/s1
comment: BRD3444 is the hit compound from a series of bicyclic azetidines with promising antimalarial activity against all lifecycle stages of the Plasmodium parasite <Reference id=33471/>. Note that BRD3444 has complex stereoisomers (PubChem same connectivity and via the UniChem InChIKey backbone search in our summary table below). The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
iupac name: (8R,9R,10S)-10-(hydroxymethyl)-N-(4-methoxyphenyl)-9-[4-(2-phenylethynyl)phenyl]-1,6-diazabicyclo[6.2.0]decane-6-carboxamide
xref: CHEMBL3560390
approved: f
ligand name: BRD3444
type: SyntheticOrganicLigand

compound 34c [PMID: 24641010]
in ch i key: XZORQADPEUSNQJ-UHFFFAOYSA-N
in ch i: InChI=1S/C22H25N5O2S/c1-13-17(14(2)27(3)26-13)12-19-24-25-22(29-19)21-20(28-15-8-10-23-11-9-15)16-6-4-5-7-18(16)30-21/h4-7,15,23H,8-12H2,1-3H3
comment: Compound 34c is from a series of benzo[b]thiophhene inhibitors with antimalarial activity. The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
iupac name: 2-(3-piperidin-4-yloxy-1-benzothiophen-2-yl)-5-[(1,3,5-trimethylpyrazol-4-yl)methyl]-1,3,4-oxadiazole
xref: CHEMBL3237438
approved: f
ligand name: compound 34c [PMID: 24641010]
type: SyntheticOrganicLigand

compound 47 [PMID: 28737909]
canonical SMILES: OCc1ccc(cc1)c1nc(N)nc2c1c(C#N)c[nH]2
isomeric SMILES: OCc1ccc(cc1)c1nc(N)nc2c1c(C#N)c[nH]2
in ch i key: BJQSJIPGTMBHKF-UHFFFAOYSA-N
in ch i: InChI=1S/C14H11N5O/c15-5-10-6-17-13-11(10)12(18-14(16)19-13)9-3-1-8(7-20)2-4-9/h1-4,6,20H,7H2,(H3,16,17,18,19)
comment: Compound 47 is one of the most potent and selective IKKα inhibitors described in <Reference id=33462/>. It inhibits agonist-stimulated NF-κB signaling of the noncanonical pathway at much lower concentrations than the canonical pathway.
iupac name: 2-Amino-4-(4-hydroxymethyl)phenyl-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile
approved: f
ligand name: compound 47 [PMID: 28737909]
type: SyntheticOrganicLigand

TAM16
in ch i key: PQGCMFVNJWTUFH-UHFFFAOYSA-N
in ch i: InChI=1S/C22H24N2O4/c1-23-22(27)20-19-16(13-24-11-3-2-4-12-24)17(26)9-10-18(19)28-21(20)14-5-7-15(25)8-6-14/h5-10,25-26H,2-4,11-13H2,1H3,(H,23,27)
comment: TAM16 is a benzofuran inhibitor of MTB Pks13 with potent in vitro bactericidal activity against drug-susceptible and drug-resistant clinical isolates of M. tuberculosis. In multiple mouse infection models it showed in vivo efficacy equal to the first-line TB drug isoniazid <Reference id=33458/>. There is PDB structure 5V3Y and the compound is example 32 in <Reference id=33459/>. Analogues are exemplified with activity data (with some gaps).
iupac name: 5-hydroxy-2-(4-hydroxyphenyl)-N-methyl-4-(piperidin-1-ylmethyl)-1-benzofuran-3-carboxamide
approved: f
ligand name: TAM16
type: SyntheticOrganicLigand

DSM265
in ch i key: OIZSVTOIBNSVOS-UHFFFAOYSA-N
in ch i: InChI=1S/C14H12F7N5S/c1-8-7-11(26-13(22-8)24-12(25-26)14(2,15)16)23-9-3-5-10(6-4-9)27(17,18,19,20)21/h3-7,23H,1-2H3
comment: DSM265 is an optimised candidate and clinical lead from the triazolopyrimidine structural class and represents a new class of antimalarial drug <Reference id=36282/>. The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
iupac name: 2-(1,1-difluoroethyl)-5-methyl-N-[4-(pentafluoro-λ6-sulfanyl)phenyl]-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine
xref: CHEMBL1956285
approved: f
ligand name: DSM265
type: SyntheticOrganicLigand

RIPA-56
canonical SMILES: CCC(C(=O)N(Cc1ccccc1)O)(C)C
isomeric SMILES: CCC(C(=O)N(Cc1ccccc1)O)(C)C
in ch i key: AVYVHIKSFXVDBG-UHFFFAOYSA-N
in ch i: InChI=1S/C13H19NO2/c1-4-13(2,3)12(15)14(16)10-11-8-6-5-7-9-11/h5-9,16H,4,10H2,1-3H3
comment: RIPA-56 is a highly potent, selective, and metabolically stable type III (allosteric) inhibitor of receptor-interacting protein kinase 1 (RIPK1) <Reference id=33450/>. It is claimed as compound 92 in patent WO2016101885 <Reference id=33451/>. RIPA-56 is a drug candidate for the treatment of systemic inflammatory response syndrome (SIRS).
iupac name: N-benzyl-N-hydroxy-2,2-dimethylbutanamide
synonym: compound 56 [PMID: 27992216]
synonym: compound 92 [WO2016101885]
approved: f
ligand name: RIPA-56
type: SyntheticOrganicLigand

TCDD
canonical SMILES: Clc1cc2Oc3cc(Cl)c(cc3Oc2cc1Cl)Cl
isomeric SMILES: Clc1cc2Oc3cc(Cl)c(cc3Oc2cc1Cl)Cl
in ch i key: HGUFODBRKLSHSI-UHFFFAOYSA-N
in ch i: InChI=1S/C12H4Cl4O2/c13-5-1-9-10(2-6(5)14)18-12-4-8(16)7(15)3-11(12)17-9/h1-4H
comment: 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD), one of the most potent non-genotoxic tumor-promoting substances known. TCDD toxicity is primarily mediated through the aryl hydrocarbon receptor (AhR) where it acts as a high-affinity ligand.
iupac name: 2,3,7,8-tetrachlorodibenzo-p-dioxin
xref: CHEMBL30327
synonym: Dioxin
synonym: 2,3,7,8-Tetrachlorodibenzo-p-dioxin
approved: f
ligand name: TCDD
type: SyntheticOrganicLigand

AMG-8718
canonical SMILES: NC1=NC2(CO1)c1cc(C#CC3(C)COC3)cnc1Oc1c2cc(cc1)c1cccnc1F
isomeric SMILES: NC1=N[C@]2(CO1)c1cc(C#CC3(C)COC3)cnc1Oc1c2cc(cc1)c1cccnc1F
in ch i key: GKKFBOARESVMBW-VWLOTQADSA-N
in ch i: InChI=1S/C25H19FN4O3/c1-24(12-31-13-24)7-6-15-9-19-22(29-11-15)33-20-5-4-16(17-3-2-8-28-21(17)26)10-18(20)25(19)14-32-23(27)30-25/h2-5,8-11H,12-14H2,1H3,(H2,27,30)/t25-/m0/s1
comment: This Amgen BACE1 inhibitor for Alzheimer's disease, AMG-8718, had a balanced profile of potency, hERG binding affinity, and Pgp recognition. It also produced robust and sustained reductions of CSF and brain Aβ levels in a rat pharmacodynamic model <Reference id=33442/>. However, retinal thinning was observed in a 1-month toxicity study in the rat and further studies suggested this to be an off-target effect where, in the rat, AMG-8718 impairs phagolysosomal function, leading to photoreceptor dysfunction and ultimately loss of photoreceptors <Reference id=33443/>. The compound is example 288 in <Reference id=33444/> from over 1000 analogues, but only binned activity data is provided. While the PubChem Bioassay data and other sources link to this structure note that MMDB and PubMed link their PDB structure to a different tautomeric representation as PubChem CID 86580376.
approved: f
ligand name: AMG-8718
type: SyntheticOrganicLigand

A77636
in ch i key: QLJOSZATCBCBDR-DFKUFRTHSA-N
in ch i: InChI=1S/C20H27NO3/c21-10-17-14-1-2-16(22)19(23)15(14)6-18(24-17)20-7-11-3-12(8-20)5-13(4-11)9-20/h1-2,11-13,17-18,22-23H,3-10,21H2/t11?,12?,13?,17-,18-,20?/m0/s1
comment: Selective D1 receptor full agonist
iupac name: (1R,3S)-3-(1-adamantyl)-1-(aminomethyl)isochroman-5,6-diol
synonym: A-77636
approved: f
ligand name: A77636
type: SyntheticOrganicLigand

inavolisib
in ch i key: SGEUNORSOZVTOL-CABZTGNLSA-N
in ch i: InChI=1S/C18H19F2N5O4/c1-9(16(21)26)22-10-2-3-11-13(6-10)28-5-4-24-7-14(23-17(11)24)25-12(15(19)20)8-29-18(25)27/h2-3,6-7,9,12,15,22H,4-5,8H2,1H3,(H2,21,26)/t9-,12-/m0/s1
comment: Inavolisib (GDC-0077) is a potent and selective, orally available PI3K-p110α (PIK3CA) inhibitor, with potential antineoplastic activity. It is example 101 in patent US20170015678 (where it is named (S)-2-((2-((S)-4-(difluoromethyl)- 2-oxooxazolidin-3-yl)-5,6- dihydrobenzo[f]imidazo[1,2- d][1,4]oxazepin-9- yl)amino)propanamide) <Reference id=33434/>. GDC-0077 is one of the agents in Genentech's oncology discovery pipeline. A preprint from May 2021 suggests that inavolisib's mechanism of action includes the ability to target oncogenic mutant PI3K-p110α for degradation, in addition to its enzyme inhibitory activity <Reference id=42311/>.
iupac name: (2S)-2-[[2-[(4S)-4-(difluoromethyl)-2-oxo-1,3-oxazolidin-3-yl]-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepin-9-yl]amino]propanamide
synonym: RG6114
synonym: GDC0077
synonym: Ro7113755
synonym: RO 7113755
synonym: GDC-0077
approved: f
ligand name: inavolisib
type: SyntheticOrganicLigand

latanoprostene bunod
in ch i key: LOVMMUBRQUFEAH-UIEAZXIASA-N
in ch i: InChI=1S/C27H41NO8/c29-22(15-14-21-10-4-3-5-11-21)16-17-24-23(25(30)20-26(24)31)12-6-1-2-7-13-27(32)35-18-8-9-19-36-28(33)34/h1,3-6,10-11,22-26,29-31H,2,7-9,12-20H2/b6-1-/t22-,23+,24+,25-,26+/m0/s1
comment: Latanoprostene bunod is a <Ligand id=2509/>-donating analogue of the prostaglandin F2α agonist <Ligand id=1961/> <Reference id=33427/>. This compound benefits from the additive hypotensive actions of both the prostaglandin agonist and NO. Latanoprostene bunod is the first NO-donating prostaglandin analogue to be granted FDA marketing approval <Reference id=33430/><Reference id=33432/>.
iupac name: 4-nitrooxybutyl (Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3R)-3-hydroxy-5-phenylpentyl]cyclopentyl]hept-5-enoate
xref: CHEMBL2364612
synonym: BOL-303259-X
synonym: PF-3187207
synonym: NCX-116
synonym: Vyzulta®
approved: t
ligand name: latanoprostene bunod
type: SyntheticOrganicLigand

compound 3 [PMID: 28603634]
in ch i key: WRBLOVAXQYYLFM-UHFFFAOYSA-N
in ch i: InChI=1S/C23H22N2O4/c1-13-7-9-18(23(28)29)15(3)20(13)25-22(27)21-14(2)8-10-19(24-21)17-6-4-5-16(11-17)12-26/h4-11,26H,12H2,1-3H3,(H,25,27)(H,28,29)
comment: EP4 antagonists from Eli Lilly are being investigated as analgesic and anti‐inflammatory molecules <Reference id=33396/>. This one is example 22 in patent US20160251306 <Reference id=33397/>, which has 43 analogues but reports only 2 IC50s.
iupac name: 3-[[6-[3-(hydroxymethyl)phenyl]-3-methylpyridine-2-carbonyl]amino]-2,4-dimethylbenzoic acid
approved: f
ligand name: compound 3 [PMID: 28603634]
type: SyntheticOrganicLigand

ZY15557
in ch i key: ROFOCLOPXHFEIE-XOKHGSTOSA-N
comment: This DPP-4 inhibitor as a potential treatment for type 2 diabetes mellitus. ZY15557 is from the Indian company Zydus Research Centre, Cadila Healthcare <Reference id=33394/>. The structure corresponds to example 17 in <Reference id=33395/>. The patent includes 257 analogues but binned IC50s for only 50.
iupac name: (2R,3S,5R)-2-(2,5-difluorophenyl)-5-(2,2-dioxo-1,3,4,6-tetrahydrothieno[3,4-c]pyrrol-5-yl)oxan-3-amine
approved: f
ligand name: ZY15557
type: SyntheticOrganicLigand

trilaciclib
in ch i key: PDGKHKMBHVFCMG-UHFFFAOYSA-N
in ch i: InChI=1S/C24H30N8O/c1-30-9-11-31(12-10-30)18-5-6-20(25-15-18)28-23-26-14-17-13-19-22(33)27-16-24(7-3-2-4-8-24)32(19)21(17)29-23/h5-6,13-15H,2-4,7-12,16H2,1H3,(H,27,33)(H,25,26,28,29)
comment: Trilaciclib (G1T28) is a short-acting CDK4/6 inhibitor that was developed by G1 Therapeutics <Reference id=33392/>.
iupac name: 2-[[5-(4-methylpiperazin-1-yl)pyridin-2-yl]amino]spiro[7,8-dihydropyrazino[5,6]pyrrolo[1,2-d]pyrimidine-9,1'-cyclohexane]-6-one
synonym: G1T28
synonym: Cosela®
approved: t
ligand name: trilaciclib
type: SyntheticOrganicLigand

rovazolac
in ch i key: ZUMNJDGBYXHASJ-UHFFFAOYSA-N
comment: This compound is claimed as example 36 in patent WO2013130892 <Reference id=33389/>, as a liver X receptor (LXR) modulator, with potential clinical utility as a topical agent for the treatment of inflammatory skin conditions. To elucidate the origins of this agent we used the IUPAC name submitted to the WHO for the INN rovazolac, which resolved to the SMILES string used to generate the chemical structure shown here. This SMILES string via SureChEMBL, identified patents claiming the structure which tracked forward to Relaxar Therapeutics disclosed development pipeline, and the research code ALX-101. However, this association is our prediction as the structure has not been formally disclosed in peer reviewed literature.
iupac name: ethyl 2-[5-[4-(3-methylsulfonylphenyl)phenyl]-3-(trifluoromethyl)pyrazol-1-yl]acetate
synonym: example 36 [WO2013130892]
synonym: A-110
synonym: ALX-101
approved: f
ligand name: rovazolac
type: SyntheticOrganicLigand

foliglurax
in ch i key: ZTEDNASHAWNBKQ-UHFFFAOYSA-N
in ch i: InChI=1S/C23H23N3O3S/c27-25-19-13-22(20-14-23-17(15-24-20)5-11-30-23)29-21-4-3-16(12-18(19)21)2-1-6-26-7-9-28-10-8-26/h3-5,11-15,27H,1-2,6-10H2
comment: Prexton Therapeutics is developing foliglurax (PXT002331), as an orally active metabotropic glutamate receptor 4 (mGluR4) positive allosteric modulator (PAM), for symptomatic relief in Parkinson's disease, as an alternative to dopamine replacement therapies. Listings on ClinicalTrials.gov associate the research code PXT002331 to the INN foliglurax. To generate the structure we used the IUPAC name submitted to the WHO for the INN foliglurax to generate SMILES using Chemicalize.
iupac name: N-{6-[3-(morpholin-4-yl)propyl]-2-{thieno[3,2-c]pyridin-6-yl}-4H-chromen-4-ylidene}hydroxylamine
synonym: PXT 002331
synonym: PXT-002331
synonym: PXT002331
approved: f
ligand name: foliglurax
type: SyntheticOrganicLigand

asivatrep
in ch i key: UKGJZDSUJSPAJL-YPUOHESYSA-N
comment: Asivatrep (PAC-14028) is an antagonist of the transient receptor potential vanilloid type 1 (TRPV1) channel, developed by AmorePacific for anti-inflammatory potential in refractory dermatoses <Reference id=33375/>. It is claimed as example 230 in patent US7858621 <Reference id=33376/>. PAC-14028 is administered topically for skin inflammation.
iupac name: (E)-N-[(1R)-1-[3,5-difluoro-4-(methanesulfonamido)phenyl]ethyl]-3-[2-propyl-6-(trifluoromethyl)pyridin-3-yl]prop-2-enamide
xref: CHEMBL3707398
synonym: Example 230 [US7858621]
synonym: PAC-14028
approved: f
ligand name: asivatrep
type: SyntheticOrganicLigand

lorecivivint
in ch i key: AQDWDWAYVBQMAM-UHFFFAOYSA-N
in ch i: InChI=1S/C29H24FN7O/c1-16(2)8-26(38)33-21-10-19(12-31-13-21)17-6-7-24-22(11-17)28(37-36-24)29-34-25-15-32-14-23(27(25)35-29)18-4-3-5-20(30)9-18/h3-7,9-16H,8H2,1-2H3,(H,33,38)(H,34,35)(H,36,37)
comment: Lorecivivint (SM04690, formerly adavivint) is a Wnt pathway inhibitor being developed by Samumed for immunomodulatory potential. It acts downstream of β-catenin, and its molecular targets are the intranuclear kinases CLK2 and DYRK1A through which it inhibits phosphorylation of serine/arginine-rich splicing factors, and SIRT1 and FOXO1 respectively <Reference id=40047/>. Wnt signalling is upregulated in tissues from osteoarthritic joints, and drives disease pathologies including inflammation <Reference id=40048/>. Wnt pathway inhibition by lorecivivint is being investigated as a disease-modifying treatment for osteoarthritis. SM04690 is example 10 as claimed in patent US20160297812 <Reference id=33370/>. The chemical structure shown here was produced using the IUPAC name submitted to the WHO for the INN adavivint (via SMILES generated using Chemicalize) which was later renamed as lorecivivint. This SMILES string resolves to PubChem CID 123710737, although some of the double bonds in the molecule are not fully resolved, when compared to the images in US20160297812. CID 89837869 is an alternative representation.
iupac name: N-(5-{3-[7-(3-fluorophenyl)-1H-imidazo[4,5-c]pyridin-2-yl]-1H-indazol-5-yl}pyridin-3-yl)-3-methylbutanamide
synonym: SM04690
synonym: SM0-4690
synonym: adavivint (deprecated INN)
approved: f
ligand name: lorecivivint
type: SyntheticOrganicLigand

fenclonine
canonical SMILES: NC(C(=O)O)Cc1ccc(cc1)Cl
isomeric SMILES: NC(C(=O)O)Cc1ccc(cc1)Cl
in ch i key: NIGWMJHCCYYCSF-UHFFFAOYSA-N
in ch i: InChI=1S/C9H10ClNO2/c10-7-3-1-6(2-4-7)5-8(11)9(12)13/h1-4,8H,5,11H2,(H,12,13)
comment: A synthetic amino acid which covalently binds to tryptophan hydroxylase to cause depletion of serotonin in the brain <Reference id=30068/>.
iupac name: 2-amino-3-(4-chlorophenyl)propanoic acid
xref: CHEMBL1256351
synonym: p-Chlorophenylalanine
synonym: 4-chlorophenylalanine
synonym: para-chlorophenylalanine
synonym: PCPA
approved: f
ligand name: fenclonine
type: SyntheticOrganicLigand

delgocitinib
in ch i key: LOWWYYZBZNSPDT-ZBEGNZNMSA-N
in ch i: InChI=1S/C16H18N6O/c1-11-8-22(13(23)2-5-17)16(11)4-7-21(9-16)15-12-3-6-18-14(12)19-10-20-15/h3,6,10-11H,2,4,7-9H2,1H3,(H,18,19,20)/t11-,16-/m0/s1
comment: Delgocitinib (JTE-052) is an ATP-competitive pna-Janus kinase (JAK) inhibitor in development for anti-inflammatory potential <Reference id=33367/>. The chemical structure is disclosed in <Reference id=39841/>. The pharmacology of JTE-052 was previously reported in <Reference id=33367/>. Based on the developer's pipeline and patent claims, and on the structure submitted to the WHO for the INN delgocitinib, JTE-052 is likely to be compound 6 as claimed in patent US20140187534 <Reference id=33368/>. Compound 6 is the most potent (lowest IC50) optically active stereoisomer with the correct structure in the patent, although stereochemistry has not rendered unambiguously in the patent extraction, and an IUPAC name is not provided.
synonym: JTE-052
synonym: JTE052
synonym: ent-60
synonym: Corectim®
approved: t
ligand name: delgocitinib
type: SyntheticOrganicLigand

iberdomide
in ch i key: IXZOHGPZAQLIBH-NRFANRHFSA-N
in ch i: InChI=1S/C25H27N3O5/c29-23-9-8-21(24(30)26-23)28-15-20-19(25(28)31)2-1-3-22(20)33-16-18-6-4-17(5-7-18)14-27-10-12-32-13-11-27/h1-7,21H,8-16H2,(H,26,29,30)/t21-/m0/s1
comment: Iberdomide (CC-220) is a novel cereblon modulator <Reference id=33360/>, functionally akin to <Ligand id=7331/> and <Ligand id=7348/>.
iupac name: (3S)-3-[7-[[4-(morpholin-4-ylmethyl)phenyl]methoxy]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione
synonym: compound 6 [PMID: 28425720]
synonym: CC-220
approved: f
ligand name: iberdomide
type: SyntheticOrganicLigand

mardepodect
in ch i key: AZEXWHKOMMASPA-UHFFFAOYSA-N
in ch i: InChI=1S/C25H20N4O/c1-29-16-23(18-12-14-26-15-13-18)25(28-29)20-7-10-22(11-8-20)30-17-21-9-6-19-4-2-3-5-24(19)27-21/h2-16H,17H2,1H3
comment: Mardepodect (PF-2545920) is a selective, orally active inhibitor of phosphodiesterase (PDE) 10A <Reference id=33358/>. Identified using structure-based drug design, the compound is optimised for selectivity, brain penetration and drug-like properties. PF-2545920 is the first PDE10A inhibitor identified as a clinical lead utilizing this mechanism for the treatment of schizophrenia.
iupac name: 2-[[4-(1-methyl-4-pyridin-4-ylpyrazol-3-yl)phenoxy]methyl]quinoline
synonym: pyrazole 9 [PMID: 19630403]
synonym: PF2545920
synonym: MP-10
synonym: PF-02545920
synonym: PF-2545920
approved: f
ligand name: mardepodect
type: SyntheticOrganicLigand

POM2-C-HMBP
in ch i key: IPOCPVGCROEFJO-NTEUORMPSA-N
in ch i: InChI=1S/C18H33O8P/c1-14(11-19)9-8-10-27(22,25-12-23-15(20)17(2,3)4)26-13-24-16(21)18(5,6)7/h9,19H,8,10-13H2,1-7H3/b14-9+
comment: POM2-C-HMBP is a synthetic, cell-permeable prodrug of the Vγ2Vδ2 effector T cell activating isoprenoid (E)-4-hydroxy-3-methyl-but-2-enyl diphosphate (HMBPP) <Reference id=33353/>. This comound shows improved internalization into target cells compared to HMBPP. Internalization was essential for engagement of BTN3A1, and the enhanced Vγ2Vδ2 effector T cell-mediated lysis of cancer cells was BTN3A1-dependent. Note that Vγ2Vδ2 effector T cells are also known as Vγ9Vδ2 cells.
iupac name: [2,2-dimethylpropanoyloxymethoxy-[(E)-5-hydroxy-4-methylpent-3-enyl]phosphoryl]oxymethyl 2,2-dimethylpropanoate
approved: f
ligand name: POM2-C-HMBP
type: SyntheticOrganicLigand

AM841
in ch i key: JCIYJYHFBBXSBF-HMXCVIKNSA-N
in ch i: InChI=1S/C26H39NO3S/c1-25(2,11-7-5-6-8-12-27-17-31)19-14-22(29)24-20-13-18(16-28)9-10-21(20)26(3,4)30-23(24)15-19/h14-15,18,20-21,28-29H,5-13,16H2,1-4H3/t18-,20-,21-/m1/s1
comment: Potent CB1 receptor agonist.
iupac name: (6aR,9R,10aR)-9-(hydroxymethyl)-3-(8-isothiocyanato-2-methyloctan-2-yl)-6,6-dimethyl-6H,6aH,7H,8H,9H,10H,10aH-benzo[c]isochromen-1-ol
synonym: AM-841
approved: f
ligand name: AM841
type: SyntheticOrganicLigand

AM11542
in ch i key: SZDVFUZKFPGYEK-WOJBJXKFSA-N
in ch i: InChI=1S/C25H37BrO2/c1-17-10-11-20-19(14-17)23-21(27)15-18(16-22(23)28-25(20,4)5)24(2,3)12-8-6-7-9-13-26/h10,15-16,19-20,27H,6-9,11-14H2,1-5H3/t19-,20-/m1/s1
comment: Potent CB1 receptor agonist.
iupac name: (6aR,10aR)-3-(8-bromo-2-methyloctan-2-yl)-6,6,9-trimethyl-6a,7,10,10a-tetrahydrobenzo[c]chromen-1-ol
approved: f
ligand name: AM11542
type: SyntheticOrganicLigand

ER-27319
canonical SMILES: NCCCn1c2ccccc2c(=O)c2c1c(C)c(C)cc2
isomeric SMILES: NCCCn1c2ccccc2c(=O)c2c1c(C)c(C)cc2
in ch i key: CFPDEQBPNROZDC-UHFFFAOYSA-N
in ch i: InChI=1S/C18H20N2O/c1-12-8-9-15-17(13(12)2)20(11-5-10-19)16-7-4-3-6-14(16)18(15)21/h3-4,6-9H,5,10-11,19H2,1-2H3
comment: The structure shown here is ER-27319 free base, when in fact the biological activity has been evaluated using the ethanedioate as represented by PubChem CID 9799508 <Reference id=33334/>. ER-27319 is an inhibitor of spleen tyrosine kinase (Syk) <Reference id=33335/> however, given the high concentration of compound ER-27319 required to cause half-maximal inhibition of mast cells degranulation, targets other than Syk may also be inhibited. In addition ER-27319 targets the activation of SYK mediated through FcεR1γ ITAM, suggesting there is no direct interaction with the Syk ATP pocket. Whatever the mechanism ER-27319 action is specific to mast cells.
iupac name: 10-(3-aminopropyl)-3,4-dimethylacridin-9-one
xref: CHEMBL1375018
approved: f
ligand name: ER-27319
type: SyntheticOrganicLigand

CBS-3595
in ch i key: CJKGORBZVWDVRY-UHFFFAOYSA-N
in ch i: InChI=1S/C18H17FN4OS/c1-11(24)21-15-10-13(8-9-20-15)17-16(22-18(25-3)23(17)2)12-4-6-14(19)7-5-12/h4-10H,1-3H3,(H,20,21,24)
comment: CBS-3595 is a dual inhibitor of p38α MAPK (MAPK14) and phosphodiesterase 4 (PDE-4) <Reference id=33333/>, a mechanism that represents a novel approach that may be useful for the treatment of pulmonary diseases (e.g. asthma and COPD) as well as other inflammatory diseases, for which there still exists a high level of unmet clinical need. The term Cytokine-Suppressive Anti-Inflammatory Drugs (CSAIDs) has been coined to describe compounds exploiting molecular mechanisms such as that targeted by CBS-3595.
iupac name: N-[4-[5-(4-fluorophenyl)-3-methyl-2-methylsulfanylimidazol-4-yl]pyridin-2-yl]acetamide
xref: CHEMBL432798
approved: f
ligand name: CBS-3595
type: SyntheticOrganicLigand

compound 76 [PMID: 28657314]
in ch i key: GWNFQAKCJYEJEW-UHFFFAOYSA-N
in ch i: InChI=1S/C30H36N6O4S/c1-4-40-29(39)21-13-12-14-22(19-21)31-27(37)17-8-6-5-7-11-18-41-30-33-32-26(35(30)2)20-25-23-15-9-10-16-24(23)28(38)36(3)34-25/h9-10,12-16,19H,4-8,11,17-18,20H2,1-3H3,(H,31,37)
comment: This is the most potent compound developed via a pharmacophore and docking-based virtual screening campaign aimed at the discovery of small molecule inhibitors of the IL-15/IL-15R interaction <Reference id=33331/>. Specifically, the investigators were searching for compounds that inhibit IL-15 binding to the IL-2Rβ subunit which together with the γ subunit, forms the signal transducing component of the IL-15R complex. Although the compound was found to be non-selective for IL-15 over IL-2, as a first in vitro SAR study it provides crucial information on the key binding interactions of IL-15 with its IL-2Rβ binding site, that will be useful for futher compound optimisation.
iupac name: ethyl 3-[8-({4-methyl-5-[(3-methyl-4-oxo-3,4-dihydrophthalazin-1-yl)methyl]-4H-1,2,4-triazol-3-yl}sulfanyl)octanamido]benzoate
approved: f
ligand name: compound 76 [PMID: 28657314]
type: SyntheticOrganicLigand

BMS-1166
in ch i key: QBXVXKRWOVBUDB-GRKNLSHJSA-N
in ch i: InChI=1S/C36H33ClN2O7/c1-22-26(6-3-7-29(22)25-8-9-32-35(14-25)44-11-10-43-32)21-46-34-16-33(45-20-24-5-2-4-23(12-24)17-38)27(13-30(34)37)18-39-19-28(40)15-31(39)36(41)42/h2-9,12-14,16,28,31,40H,10-11,15,18-21H2,1H3,(H,41,42)/t28-,31-/m1/s1
comment: BMS-1166 is a small molecule that disrupts the PD-1/PD-L1 immune checkpoint interaction. It is the most potent of the [3-(2,3-Dihydro-1,4-benzodioxin-6-yl)-2-methylphenyl]methanol derivatives described in <Reference id=33329/>, and it is claimed as Example 1166 in Bristol-Myers Squibb's patent WO2015160641A2 <Reference id=36712/>. NMR analysis suggests that BMS-1166 promotes the formation of dimeric PD-L1 in solution.
iupac name: (2R,4R)-1-[[5-chloro-2-[(3-cyanophenyl)methoxy]-4-[[3-(2,3-dihydro-1,4-benzodioxin-6-yl)-2-methylphenyl]methoxy]phenyl]methyl]-4-hydroxypyrrolidine-2-carboxylic acid
synonym: compound 2c [PMID: 28613862]
synonym: Example 1166 [WO2015160641A2]
approved: f
ligand name: BMS-1166
type: SyntheticOrganicLigand

BMS-202
in ch i key: JEDPSOYOYVELLZ-UHFFFAOYSA-N
in ch i: InChI=1S/C25H29N3O3/c1-18-22(10-7-11-23(18)20-8-5-4-6-9-20)17-31-24-13-12-21(25(28-24)30-3)16-26-14-15-27-19(2)29/h4-13,26H,14-17H2,1-3H3,(H,27,29)
comment: BMS-202 is a small molecule that disrupts the PD-1/PD-L1 immune checkpoint interaction. It is the most potent of the (2-methyl-3-biphenylyl)methanol derivatives described in <Reference id=33329/>. NMR analysis suggests that BMS-202 promotes the formation of dimeric PD-L1 in solution. The X-ray crystal structure of the complex is deposited in the PDB, with accession 5J89 <Reference id=33330/>.
iupac name: N-[2-[[2-methoxy-6-[(2-methyl-3-phenylphenyl)methoxy]pyridin-3-yl]methylamino]ethyl]acetamide
synonym: compound 1c [PMID: 28613862]
synonym: PD1-PDL1 inhibitor 2
approved: f
ligand name: BMS-202
type: SyntheticOrganicLigand

clodronic acid
canonical SMILES: ClC(P(=O)(O)O)(P(=O)(O)O)Cl
isomeric SMILES: ClC(P(=O)(O)O)(P(=O)(O)O)Cl
in ch i key: ACSIXWWBWUQEHA-UHFFFAOYSA-N
in ch i: InChI=1S/CH4Cl2O6P2/c2-1(3,10(4,5)6)11(7,8)9/h(H2,4,5,6)(H2,7,8,9)
comment: Clodronic acid is a first generation (non-nitrogenous) bisphosphonate drug. Clinically used drugs can contain sodium clodronate tetrahydrate, sodium clodronate, disodium clodronate tetrahydrate or disodium clodronate. Kato et al. (2017) report that clodronic acid-mediated inhibition of the vesicular nucleotide transporter (VNUT, SLC17A9) suggests that this drug has potential as a transporter-targeted (and notably, non-opioid) analgesic drug for the treatment of chronic neuropathic and inflammatory pain <Reference id=33328/>. In this study clodronic acid was selective for VNUT compared to other vesicular transporters tested.
iupac name: (dichloro-phosphonomethyl)phosphonic acid
xref: CHEMBL12318
synonym: clodronate
synonym: Bonefos®
synonym: Clasteon ®
synonym: Loron®
approved: t
ligand name: clodronic acid
type: SyntheticOrganicLigand

BIA 10-2639
canonical SMILES: CN(C(=O)n1cnc(c1)c1cccnc1)C1CCCCC1
isomeric SMILES: CN(C(=O)n1cnc(c1)c1cccnc1)C1CCCCC1
in ch i key: DWCWWJONKWHPDD-UHFFFAOYSA-N
in ch i: InChI=1S/C16H20N4O/c1-19(14-7-3-2-4-8-14)16(21)20-11-15(18-12-20)13-6-5-9-17-10-13/h5-6,9-12,14H,2-4,7-8H2,1H3
comment: BIA 10-2639 is a confirmed metabolite of the irreversible FAAH inhibitor <Ligand id=9001/>, in which the N-oxide of BIA 10-2474 has been reduced to a pyridine <Reference id=33310/>.
iupac name: N-cyclohexyl-N-methyl-4-pyridin-3-ylimidazole-1-carboxamide
approved: f
ligand name: BIA 10-2639
type: SyntheticOrganicLigand

betrixaban
in ch i key: XHOLNRLADUSQLD-UHFFFAOYSA-N
in ch i: InChI=1S/C23H22ClN5O3/c1-29(2)21(25)14-4-6-15(7-5-14)22(30)27-19-10-9-17(32-3)12-18(19)23(31)28-20-11-8-16(24)13-26-20/h4-13,25H,1-3H3,(H,27,30)(H,26,28,31)
comment: Betrixaban is an orally active direct factor Xa inhibitor <Reference id=33261/>, that is an approved anti-thrombotic.
iupac name: N-(5-chloropyridin-2-yl)-2-[[4-(N,N-dimethylcarbamimidoyl)benzoyl]amino]-5-methoxybenzamide
xref: CHEMBL512351
synonym: Bevyxxa®
synonym: PRT054021
synonym: PRT-054021
synonym: PRT 054021
synonym: compound 11 [PMID: 19297154]
approved: t
ligand name: betrixaban
type: SyntheticOrganicLigand

catequentinib
in ch i key: KSMZEXLVHXZPEF-UHFFFAOYSA-N
in ch i: InChI=1S/C23H22FN3O3/c1-13-9-15-16(27-13)3-4-19(22(15)24)30-18-5-8-26-17-11-21(20(28-2)10-14(17)18)29-12-23(25)6-7-23/h3-5,8-11,27H,6-7,12,25H2,1-2H3
comment: Catequentinib (AL3818; anlotinib in China) is a non-selective inhibitor of multiple receptor tyrosine kinases, including vascular endothelial growth factor receptor type 2 (VEGFR-2, FLT1) and type 3 (VEGFR-3, FLT4). It is being investigated for antineoplastic and anti-angiogenic potential. The dihydrochloride has PubChem CID 57380530. Preparation and crystallisation of AL3818 is described in patent WO2016179123 <Reference id=33259/>. Note that anlotinib appears to be a 'pseudo' INN, that uses the -tinib INN stem for tyrosine kinase inhibitors, but has not been submitted to the World Health Organisation for ratification, and in fact a genuine INN request for 'catequentinib' was submitted for this chemical structure to the WHO (in Proposed List 121) and this became the recommended INN in April 2020..
iupac name: 1-[[4-[(4-fluoro-2-methyl-1H-indol-5-yl)oxy]-6-methoxyquinolin-7-yl]oxymethyl]cyclopropan-1-amine
synonym: AL3818
synonym: AL-3818
synonym: AL 3818
synonym: anlotinib
approved: t
ligand name: catequentinib
type: SyntheticOrganicLigand

mivavotinib
in ch i key: MJHOMTRKVMKCNE-NWDGAFQWSA-N
in ch i: InChI=1S/C17H21FN6O/c1-24-8-9(6-21-24)15-13-10(7-20-17(13)25)14(18)16(23-15)22-12-5-3-2-4-11(12)19/h6,8,11-12H,2-5,7,19H2,1H3,(H,20,25)(H,22,23)/t11-,12+/m0/s1
comment: Mivavotinib (TAK-659) an orally available inhibitor of spleen tyrosine kinase (SYK), which is in clinical development for solid tumour and lymphoma malignancies. We have drawn the structure as represented in <Reference id=33257/>.
iupac name: 6-[[(1R,2S)-2-aminocyclohexyl]amino]-7-fluoro-4-(1-methylpyrazol-4-yl)-1,2-dihydropyrrolo[3,4-c]pyridin-3-one
synonym: compound 3b [PMID: 27839918]
synonym: TAK-659
synonym: TAK659
synonym: TAK 659
approved: f
ligand name: mivavotinib
type: SyntheticOrganicLigand

isosorbide mononitrate
canonical SMILES: [O-][N+](=O)OC1COC2C1OCC2O
isomeric SMILES: [O-][N+](=O)O[C@@H]1CO[C@H]2[C@@H]1OC[C@@H]2O
in ch i key: YWXYYJSYQOXTPL-SLPGGIOYSA-N
in ch i: InChI=1S/C6H9NO6/c8-3-1-11-6-4(13-7(9)10)2-12-5(3)6/h3-6,8H,1-2H2/t3-,4+,5+,6+/m0/s1
comment: Isosorbide mononitrate is termed a nitrate drug and acts as a vasodilator. It is similar to nitroglycerin, but is slower to act.
iupac name: [(3R,3aS,6S,6aR)-6-hydroxy-2,3,3a,5,6,6a-hexahydrofuro[2,3-d]furan-3-yl] nitrate
xref: CHEMBL1311
synonym: IS-5-MN
synonym: BM-22-145
synonym: AHR-4698
synonym: Monoket
synonym: Imdur®
synonym: ISMN
synonym: Monosorb®
synonym: Chemydur
synonym: Isonorm
synonym: Monotrate
synonym: Solotrate
synonym: Monit
approved: t
ligand name: isosorbide mononitrate
type: SyntheticOrganicLigand

RG7112
in ch i key: QBGKPEROWUKSBK-QPPIDDCLSA-N
comment: RG7112 is a clinical small-molecule MDM2 inhibitor designed to occupy the p53-binding pocket. In cancer cells expressing wild-type p53, this compound stabilizes it and activates the p53 pathway, leading to cell cycle arrest, apoptosis, and inhibition or regression of human tumour xenografts <Reference id=33255/>.
iupac name: [(4S,5R)-2-(4-tert-butyl-2-ethoxyphenyl)-4,5-bis(4-chlorophenyl)-4,5-dimethylimidazol-1-yl]-[4-(3-methylsulfonylpropyl)piperazin-1-yl]methanone
xref: CHEMBL2386346
approved: f
ligand name: RG7112
type: SyntheticOrganicLigand

ML324
in ch i key: QDBVSOZTVKXUES-UHFFFAOYSA-N
in ch i: InChI=1S/C21H23N3O2/c1-24(2)12-4-11-23-21(26)16-8-6-15(7-9-16)18-13-17-5-3-10-22-20(17)19(25)14-18/h3,5-10,13-14,25H,4,11-12H2,1-2H3,(H,23,26)
comment: ML324 is a cell-permeable, small molecule inhibitor of lysine demethylase 4 (KDM4) family of histone modifying enzymes <Reference id=33194/>. KDM4 demethylases are responsible for the removal of H3K9 trimethylation marks from histones. The family members exhibit substantial mechanistic redundancy <Reference id=33195/>. ML324 demonstrates antiviral activity and is one of the chemotypes included in the Medicines for Malaria Pandemic Response Box (MMV PRB). The compound also has antimalarial activity. The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
iupac name: N-[3-(dimethylamino)propyl]-4-(8-hydroxyquinolin-6-yl)benzamide
xref: CHEMBL1398529
synonym: ML-324
synonym: MMV1580488
synonym: ML 324
approved: f
ligand name: ML324
type: SyntheticOrganicLigand

psora-4
canonical SMILES: O=c1ccc2c(o1)cc1c(c2OCCCCc2ccccc2)cco1
isomeric SMILES: O=c1ccc2c(o1)cc1c(c2OCCCCc2ccccc2)cco1
in ch i key: JJAWGNIQEOFURP-UHFFFAOYSA-N
in ch i: InChI=1S/C21H18O4/c22-20-10-9-16-19(25-20)14-18-17(11-13-23-18)21(16)24-12-5-4-8-15-6-2-1-3-7-15/h1-3,6-7,9-11,13-14H,4-5,8,12H2
comment: Psora-4 is a potent small molecule Kv1.3 channel blocker. It preferentially binds the C-type inactivated state of the channel.
iupac name: 4-(4-phenylbutoxy)furo[3,2-g]chromen-7-one
xref: CHEMBL1256851
synonym: 5-(4-phenylbutoxy)psoralen
synonym: psora 4
approved: f
ligand name: psora-4
type: SyntheticOrganicLigand

ARN-3236
canonical SMILES: COc1cc(OC)ccc1c1c[nH]c2c1c(ccn2)c1cscc1
isomeric SMILES: COc1cc(OC)ccc1c1c[nH]c2c1c(ccn2)c1cscc1
in ch i key: WEHOIIGXTMKVRG-UHFFFAOYSA-N
in ch i: InChI=1S/C19H16N2O2S/c1-22-13-3-4-15(17(9-13)23-2)16-10-21-19-18(16)14(5-7-20-19)12-6-8-24-11-12/h3-11H,1-2H3,(H,20,21)
comment: ARN-3236 is an orally active, ATP-competitive inhibitor of salt-inducible kinases (SIKs) <Reference id=33182/>. It is one of the chemical structures claimed in patent WO2014093383, in which it is referred to as Example 86 or compound 114 <Reference id=33185/>.
iupac name: 3-(2,4-dimethoxyphenyl)-4-thiophen-3-yl-1H-pyrrolo[2,3-b]pyridine
synonym: example 86 [WO2014093383]
approved: f
ligand name: ARN-3236
type: SyntheticOrganicLigand

MPI-0485520
in ch i key: DHPSFJYFPJRCTN-UHFFFAOYSA-N
in ch i: InChI=1S/C23H20N6O/c24-14-17-11-15(3-6-21(17)29-9-1-2-10-29)20-7-8-25-23(28-20)26-18-4-5-19-16(12-18)13-22(30)27-19/h3-8,11-12H,1-2,9-10,13H2,(H,27,30)(H,25,26,28)
comment: MPI-0485520 (MPC-9528) is a potent and highly selective small molecule inhibitor TBK1/ and IKKε. It is one of 80 structures claimed in Domainex's patent WO2012010826, where it is referred to as DMX-14 <Reference id=33178/>.
xref: CHEMBL3650697
synonym: MPI-485520
synonym: MPC-9528
approved: f
ligand name: MPI-0485520
type: SyntheticOrganicLigand

compound II [PMID: 21329883]
in ch i key: DRSHXJFUUPIBHX-UHFFFAOYSA-N
in ch i: InChI=1S/C28H37N7O4/c1-33-11-13-34(14-12-33)10-5-15-39-25-17-21(16-24(37-3)26(25)38-4)31-28-29-18-20-19-30-35(27(20)32-28)22-6-8-23(36-2)9-7-22/h6-9,16-20,27H,5,10-15H2,1-4H3,(H,31,32)
comment: Compound II [PMID: 21329883] is an inhibitor of the atypical IκK kinase TANK-binding kinase 1 (TBK1) <Reference id=33177/>. TBK1 couples pathogen surveillance to induction of innate immune signaling, regulating the type I interferon response as a host defense mechanism.
iupac name: N-{3,4-dimethoxy-5-[3-(4-methylpiperazin-1-yl)propoxy]phenyl}-1-(4-methoxyphenyl)-1H,3aH,7aH-pyrazolo[3,4-d]pyrimidin-6-amine
approved: f
ligand name: compound II [PMID: 21329883]
type: SyntheticOrganicLigand

SR8185
in ch i key: MQAQKNLCUSPSAF-UHFFFAOYSA-N
in ch i: InChI=1S/C26H27N7O/c27-18-20-16-19(8-9-24(20)32-12-1-2-13-32)23-10-11-28-25(31-23)29-21-6-5-7-22(17-21)30-26(34)33-14-3-4-15-33/h5-11,16-17H,1-4,12-15H2,(H,30,34)(H,28,29,31)
comment: SR8185 is a dual TBK1/IKK-ε inhibitor <Reference id=33176/>.
iupac name: N-[3-[[4-(3-cyano-4-pyrrolidin-1-ylphenyl)pyrimidin-2-yl]amino]phenyl]pyrrolidine-1-carboxamide
synonym: SR-8185
approved: f
ligand name: SR8185
type: SyntheticOrganicLigand

AZ13102909
in ch i key: UMLDEMVOMRDOLS-UHFFFAOYSA-N
in ch i: InChI=1S/C30H37N7O3/c1-40-23-14-12-20(13-15-23)19-8-10-21(11-9-19)28-35-26-25(24(27(31)38)18-33-29(26)36-28)37-34-17-5-16-32-30(39)22-6-3-2-4-7-22/h8-15,18,22,28-29,34,36-37H,2-7,16-17H2,1H3,(H2,31,38)(H,32,39)
comment: AZ13102909 is an inhibitor of the atypical IκB kinase TANK-binding kinase 1 (TBK1) <Reference id=33126/><Reference id=33175/>.
iupac name: 7-{2-[3-(cyclohexylformamido)propyl]hydrazin-1-yl}-2-{4'-methoxy-[1,1'-biphenyl]-4-yl}-2H,3H,3aH-imidazo[4,5-b]pyridine-6-carboxamide
synonym: AZ909
approved: f
ligand name: AZ13102909
type: SyntheticOrganicLigand

TC114
canonical SMILES: CN(C(=O)c1ccc(cc1C(F)(F)F)[N+](=O)[O-])C1CCN(CC1)c1nnc(c2c1cccc2)c1ccnn1C
isomeric SMILES: CN(C(=O)c1ccc(cc1C(F)(F)F)[N+](=O)[O-])C1CCN(CC1)c1nnc(c2c1cccc2)c1ccnn1C
in ch i key: ZDEZQXNVPSUJHK-UHFFFAOYSA-N
in ch i: InChI=1S/C26H24F3N7O3/c1-33(25(37)20-8-7-17(36(38)39)15-21(20)26(27,28)29)16-10-13-35(14-11-16)24-19-6-4-3-5-18(19)23(31-32-24)22-9-12-30-34(22)2/h3-9,12,15-16H,10-11,13-14H2,1-2H3
comment: TC114 is a probe that significantly stabilizes and locks the SMO into a single conformation.
iupac name: N-methyl-N-{1-[4-(2-methylpyrazol-3-yl)phthalazin-1-yl]piperidin-4-yl}-4-nitro-2-(trifluoromethyl)benzamide
approved: f
ligand name: TC114
type: SyntheticOrganicLigand

PF-06372222
in ch i key: MYZIDYJMNWEJMC-QHCPKHFHSA-N
in ch i: InChI=1S/C26H28F3N5O3/c1-25(2)11-18(12-25)23(16-3-5-17(6-4-16)24(37)30-10-9-22(35)36)33-19-7-8-21(31-13-19)34-14-20(32-15-34)26(27,28)29/h3-8,13-15,18,23,33H,9-12H2,1-2H3,(H,30,37)(H,35,36)/t23-/m0/s1
comment: Negative allosteric modulator of the GLP-1 receptor.
iupac name: 3-[[4-[(R)-(3,3-dimethylcyclobutyl)-[[6-[4-(trifluoromethyl)imidazol-1-yl]pyridin-3-yl]amino]methyl]benzoyl]amino]propanoic acid
approved: f
ligand name: PF-06372222
type: SyntheticOrganicLigand

NNC0640
in ch i key: PPTKULJUDJWTSA-UHFFFAOYSA-N
in ch i: InChI=1S/C29H31N7O4S/c1-41(39,40)26-9-5-8-24(18-26)30-29(38)36(25-16-14-22(15-17-25)21-6-3-2-4-7-21)19-20-10-12-23(13-11-20)27(37)31-28-32-34-35-33-28/h5,8-18,21H,2-4,6-7,19H2,1H3,(H,30,38)(H2,31,32,33,34,35,37)
comment: Negative allosteric modulator of the human glucagon receptor <Reference id=33119/>.
approved: f
ligand name: NNC0640
type: SyntheticOrganicLigand

Bis1
in ch i key: ADHYVMBQQIBLSN-WQGIEDEVSA-N
comment: Bis1 is a thiazole analogue of the marine cyanobacterium‐derived linear amide, bisebromoamide (BBA; PubChem CID 44520348) <Reference id=33098/>. BBA is a nonribosomal peptide that is synthesised in cyanobacteria in a process involving nonribosomal peptide synthetase (NRPS) enzyme complexes. The IUPAC condensed name for this peptide is pivaloyl-Ala-N(Me)D-Tyr(3-Br)-Unk-D-Leu-N(Me)Phe-Pro-Et.
iupac name: (2S)-1-[N-[[(4S)-2-[(2S)-1-(N-Pivaloyl-L-Ala-N-methyl-3-bromo-D-Tyr-)-4alpha-methylpyrrolidine-2alpha-yl]-2-thiazoline-4beta-yl]carbonyl]-D-Leu-N-methyl-L-Phe-]-2alpha-propanoylpyrrolidine
synonym: Tz‐BBA
approved: f
ligand name: Bis1
type: NaturalProductLigand

eCF309
in ch i key: PSICWGWNIOOULV-UHFFFAOYSA-N
in ch i: InChI=1S/C18H21N7O3/c1-3-26-13(27-4-2)8-25-17-14(16(19)21-9-22-17)15(24-25)10-5-6-12-11(7-10)23-18(20)28-12/h5-7,9,13H,3-4,8H2,1-2H3,(H2,20,23)(H2,19,21,22)
comment: eCF309 is a low nanomolar potency, selective and cell-permeable mTOR inhibitor <Reference id=33097/>.
iupac name: 5-[4-amino-1-(2,2-diethoxyethyl)pyrazolo[3,4-d]pyrimidin-3-yl]-1,3-benzoxazol-2-amine
synonym: eCF 309
synonym: eCF-309
synonym: compound 12 [Fraser et al., 2016]
approved: f
ligand name: eCF309
type: SyntheticOrganicLigand

paracetamol
canonical SMILES: CC(=O)Nc1ccc(cc1)O
isomeric SMILES: CC(=O)Nc1ccc(cc1)O
in ch i key: RZVAJINKPMORJF-UHFFFAOYSA-N
in ch i: InChI=1S/C8H9NO2/c1-6(10)9-7-2-4-8(11)5-3-7/h2-5,11H,1H3,(H,9,10)
comment: Paracetamol is approved by the US FDA as acetaminophen. Paracetamol is a widely used analgesic and antipyretic drug.
iupac name: N-(4-hydroxyphenyl)acetamide
xref: CHEMBL112
synonym: Multin
synonym: acetaminophen
synonym: Abenol
synonym: Abensanil
synonym: Acamol
synonym: Accu-Tap
synonym: Acephen
synonym: Aceta Elixir
synonym: Aceta Tablets
synonym: Acetagesic
synonym: Acetalgin
synonym: Actamin
synonym: Actimol
synonym: Algotropyl
synonym: Alpiny
synonym: Alpinyl
synonym: Alvedon
synonym: Amadil
synonym: Aminofen
synonym: Anacin-3
synonym: Anaflon
synonym: Anapap
synonym: Anelix
synonym: Anhiba
synonym: Apacet
synonym: Apadon
synonym: Apamide
synonym: Atasol
synonym: Banesin
synonym: Bayer Select
synonym: Bickie-mol
synonym: Calpol
synonym: Captin
synonym: Cetadol
synonym: Clixodyne
synonym: Conacetol
synonym: Dafalgan
synonym: Dapa X-S
synonym: Darvocet
synonym: Datril
synonym: Dimindol
synonym: Dirox
synonym: Disprol
synonym: Doliprane
synonym: Dolprone
synonym: Drixoral Plus
synonym: Dularin
synonym: Dymadon
synonym: Dypap
synonym: Elixodyne
synonym: Enelfa
synonym: Eneril
synonym: Eu-Med
synonym: Exdol
synonym: Febridol
synonym: Febrilix
synonym: Febrinol
synonym: Febro-Gesic
synonym: Febrolin
synonym: Fendon
synonym: Feverall
synonym: Fevor
synonym: Finimal
synonym: Gelocatil
synonym: Genapap
synonym: Genebs
synonym: Hedex
synonym: Homoolan
synonym: Injectapap
synonym: Janupap
synonym: Korum
synonym: Lestemp
synonym: Liquagesic

C391
in ch i key: OHQDORKALTUSJJ-ZHLQKWORSA-N
in ch i: InChI=1S/C38H53N7O10/c1-22(2)16-26(34(49)42-27(38(53)54)18-24-10-12-25(46)13-11-24)41-35(50)29(8-5-6-14-39)43-20-32-44(37(52)30-9-7-15-55-30)19-28(40-31(47)17-23(3)4)36(51)45(32)21-33(43)48/h7,9-13,15,22-23,26-29,32,46H,5-6,8,14,16-21,39H2,1-4H3,(H,40,47)(H,41,50)(H,42,49)(H,53,54)/t26-,27-,28-,29-,32?/m0/s1
comment: C391 is a protease activated receptor 2 (PAR2) antagonist <Reference id=33090/>. It is a small peptidomimetic derivative of the PAR2 agonist <Ligand id=3851/> <Reference id=33091/>. PAR2 antagonists have potential for treating inflammatory, respiratory, gastrointestinal, neurological, and metabolic disorders.
synonym: compound 5 [PMID: 27994760]
approved: f
ligand name: C391
type: SyntheticOrganicLigand

ASP4058
in ch i key: NJNXCJPSMWKXHO-VIFPVBQESA-N
in ch i: InChI=1S/C19H12F6N4O2/c1-9(18(20,21)22)30-15-5-3-11(6-12(15)19(23,24)25)17-28-16(29-31-17)10-2-4-13-14(7-10)27-8-26-13/h2-9H,1H3,(H,26,27)/t9-/m0/s1
comment: ASP4058 is an orally active, next-generation sphingosine 1-phosphate (S1P) receptor agonist that shows selectivity for S1P1 and S1P5 over other S1P receptors in vitro <Reference id=33086/>. Most likely used as the hydrochloride salt (PubChem CID 16755142). Compare this with the non-selective S1P agonist <Ligand id=2407/>, which was the first oral drug to be approved for relapsing forms of MS. Studies in animal models suggests that ASP4058 may also be beneficial in ameliorating the chronic arterial wall inflammation observed as underlying intracranial aneurysm (IA) <Reference id=33088/>.
iupac name: 5-(5-(3-(Trifluoromethyl)-4-(((2S)-1,1,1-trifluoropropan-2-yl)oxy)phenyl)-1,2,4-oxadiazol-3-yl)-1H-benzimidazole
synonym: ASP-4058
approved: f
ligand name: ASP4058
type: SyntheticOrganicLigand

TAN-67
in ch i key: LEPBHAAYNPPRRA-WMZHIEFXSA-N
in ch i: InChI=1S/C23H24N2O/c1-25-10-9-23(18-6-4-7-20(26)13-18)14-22-17(12-19(23)15-25)11-16-5-2-3-8-21(16)24-22/h2-8,11,13,19,26H,9-10,12,14-15H2,1H3/t19-,23+/m0/s1
comment: TAN-67 is a potent and selective δ-opioid receptor agonist <Reference id=33076/>. It is also an agonist of the orphan GPCR MRGPRX2 <Reference id=33074/>.
iupac name: 3-[(4aS,12aR)-2-methyl-1,3,4,5,12,12a-hexahydropyrido[3,4-b]acridin-4a-yl]phenol
xref: CHEMBL327745
synonym: SB-213698
synonym: SB-205,607
synonym: (-)-TAN-67
approved: f
ligand name: TAN-67
type: SyntheticOrganicLigand

(R)-ZINC-3573
canonical SMILES: CN(C1CCN(C1)c1cc(nc2n1ncc2)c1ccccc1)C
in ch i key: XKBSPAZCFAIBJL-OAHLLOKOSA-N
in ch i: InChI=1S/C18H21N5/c1-21(2)15-9-11-22(13-15)18-12-16(14-6-4-3-5-7-14)20-17-8-10-19-23(17)18/h3-8,10,12,15H,9,11,13H2,1-2H3/t15-/m1/s1
comment: (R)-ZINC-3573 is a selective probe for the orphan GPCR, MAS-related G protein-coupled receptor member X2 (MRGPRX2) <Reference id=33074/>. The (S)-enantiomer is inactive at this receptor.
iupac name: (3R)-N,N-dimethyl-1-(5-phenylpyrazolo[1,5-a]pyrimidin-7-yl)pyrrolidin-3-amine
synonym: ZINC-72453573
synonym: ZINC72453573
approved: f
ligand name: (R)-ZINC-3573
type: SyntheticOrganicLigand

PF-06840003
canonical SMILES: Fc1cc2c(C3CC(=O)NC3=O)c[nH]c2cc1
isomeric SMILES: Fc1cc2c(C3CC(=O)NC3=O)c[nH]c2cc1
in ch i key: MXKLDYKORJEOPR-UHFFFAOYSA-N
in ch i: InChI=1S/C12H9FN2O2/c13-6-1-2-10-7(3-6)9(5-14-10)8-4-11(16)15-12(8)17/h1-3,5,8,14H,4H2,(H,15,16,17)
comment: PF-06840003 is a small molecule IDO1 inhibitor, designed as a cancer immunotherapeutic. It is claimed as compound 1 in patent WO2015173764 <Reference id=33072/>.
iupac name: 3-(5-fluoro-1H-indol-3-yl)pyrrolidine-2,5-dione
synonym: EOS200271
synonym: PF06840003
approved: f
ligand name: PF-06840003
type: SyntheticOrganicLigand

3 alpha-aminocholestane
in ch i key: RJNGJYWAIUJHOJ-DSHIFKSRSA-N
in ch i: InChI=1S/C27H49N/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h18-25H,6-17,28H2,1-5H3/t19-,20?,21-,22+,23-,24+,25+,26+,27-/m1/s1
comment: 3AC is an inhibitor of inositol polyphosphate-5-phosphatase D (INPP5D) <Reference id=33069/>, an enzyme with a role in controlling immune regulatory cell numbers in vivo. INPP5D is more commonly referred to as SHIP1. SHIP1 inhibitors are being investigated as novel agents with potential clinical application in allogeneic transplantation and the treatment of hematologic malignancies.
iupac name: (3R,8R,9S,10S,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-amine
synonym: 3 α-aminocholestane
approved: f
ligand name: 3 alpha-aminocholestane
type: SyntheticOrganicLigand

eganelisib
in ch i key: XUMALORDVCFWKV-IBGZPJMESA-N
in ch i: InChI=1S/C30H24N8O2/c1-19(34-29(39)26-27(31)35-37-15-7-14-32-28(26)37)24-16-22-9-6-8-21(13-12-20-17-33-36(2)18-20)25(22)30(40)38(24)23-10-4-3-5-11-23/h3-11,14-19H,1-2H3,(H2,31,35)(H,34,39)/t19-/m0/s1
comment: Eganelisib (IPI549) is an orally bioavailable, highly selective small molecule PI3Kγ inhibitor <Reference id=33066/>.
iupac name: 2-amino-N-[(1S)-1-[8-[2-(1-methylpyrazol-4-yl)ethynyl]-1-oxo-2-phenylisoquinolin-3-yl]ethyl]pyrazolo[1,5-a]pyrimidine-3-carboxamide
synonym: IPI-549
synonym: compound 26 [PMID: 27660692]
synonym: IPI549
approved: f
ligand name: eganelisib
type: SyntheticOrganicLigand

ziritaxestat
canonical SMILES: CCc1nc2n(c1N(c1sc(c(n1)c1ccc(cc1)F)C#N)C)cc(cc2C)N1CCN(CC1)CC(=O)N1CC(C1)O
isomeric SMILES: CCc1nc2n(c1N(c1sc(c(n1)c1ccc(cc1)F)C#N)C)cc(cc2C)N1CCN(CC1)CC(=O)N1CC(C1)O
in ch i key: REQQVBGILUTQNN-UHFFFAOYSA-N
in ch i: InChI=1S/C30H33FN8O2S/c1-4-24-29(35(3)30-34-27(25(14-32)42-30)20-5-7-21(31)8-6-20)39-15-22(13-19(2)28(39)33-24)37-11-9-36(10-12-37)18-26(41)38-16-23(40)17-38/h5-8,13,15,23,40H,4,9-12,16-18H2,1-3H3
comment: Ziritaxestat (GLPG1690) is a selective autotaxin Inhibitor <Reference id=33057/>, that was investigated for anti-fibrotic efficacy. Animal studies using GLPG1690 suggested potential for autotaxin inhibition in breast cancer treatment <Reference id=39882/><Reference id=39883/> and TSC2-loss associated oncogenicity (in tuberous sclerosis complex) <Reference id=39884/>. In early 2021 data from the phase 3 ziritaxestat program in idiopathic pulmonary fibrosis (IPF; ISABELA) was analysed, and the conclusion reached was that ziritaxestat's benefit-risk profile did not support continuing the program. At that time the decision was made to discontinue the inhibitor's phase 2 trial in systemic sclerosis.
iupac name: 2-[[2-ethyl-6-[4-[2-(3-hydroxyazetidin-1-yl)-2-oxoethyl]piperazin-1-yl]-8-methylimidazo[1,2-a]pyridin-3-yl]-methylamino]-4-(4-fluorophenyl)-1,3-thiazole-5-carbonitrile
xref: CHEMBL3828074
synonym: GLPG1690
synonym: GLPG-1690
synonym: compound 11 [PMID: 28414242]
approved: f
ligand name: ziritaxestat
type: SyntheticOrganicLigand

AZ3451
in ch i key: FJAOGFGHTPYADT-SFHVURJKSA-N
in ch i: InChI=1S/C30H27BrN4O3/c1-18(20-5-3-2-4-6-20)35-26-12-9-21(30(36)33-22-10-7-19(16-32)8-11-22)13-25(26)34-29(35)23-14-27-28(15-24(23)31)38-17-37-27/h7-15,18,20H,2-6,17H2,1H3,(H,33,36)/t18-/m0/s1
comment: AZ3451 is a negative allosteric modulator of protease-activated receptor 2 (PAR2) that prevents receptor activation and signalling <Reference id=33052/>. Substantial evidence indicates that PARs are involved in inflammatory disease, with roles in causing inflammatory reactions in peripheral limb tissue, and modulating arthritic joint inflammation and pain.
iupac name: 2-(6-bromanyl-1,3-benzodioxol-5-yl)-~{N}-(4-cyanophenyl)-1-[(1~{S})-1-cyclohexylethyl]benzimidazole-5-carboxamide
approved: f
ligand name: AZ3451
type: SyntheticOrganicLigand

ritlecitinib
canonical SMILES: C=CC(=O)N1CC(CCC1C)Nc1ncnc2c1cc[nH]2
in ch i key: CBRJPFGIXUFMTM-WDEREUQCSA-N
in ch i: InChI=1S/C15H19N5O/c1-3-13(21)20-8-11(5-4-10(20)2)19-15-12-6-7-16-14(12)17-9-18-15/h3,6-7,9-11H,1,4-5,8H2,2H3,(H2,16,17,18,19)/t10-,11+/m0/s1
comment: Ritlecitinib (PF-06651600) is a potent, orally active, selective covalent inhibitor of Janus kinase 3 (JAK3) <Reference id=33049/>, with anti-inflammatory activity in in vivo models <Reference id=33051/>. It is example 5 in a Pfizer patent that provides SAR for 343 analogues <Reference id=33050/>. There are three crystal structures available for compounds reported in <Reference id=33049/> with JAK3, but not for compound 11 (the PDB identifiers are 5TTV, 5TTU and 5TTS). Pfizer's pipeline webpage indicates that the ritlecitinib program has been discontinued.
iupac name: 1-[(2S,5R)-2-methyl-5-(7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)piperidin-1-yl]prop-2-en-1-one
synonym: PF-06651600
synonym: PF06651600
synonym: compound 11 [PMID: 28139931]
synonym: example 5 [WO2015083028]
approved: f
ligand name: ritlecitinib
type: SyntheticOrganicLigand

belumosudil
in ch i key: GKHIVNAUVKXIIY-UHFFFAOYSA-N
in ch i: InChI=1S/C26H24N6O2/c1-16(2)28-24(33)15-34-20-7-5-6-17(13-20)25-30-23-9-4-3-8-21(23)26(31-25)29-19-10-11-22-18(12-19)14-27-32-22/h3-14,16H,15H2,1-2H3,(H,27,32)(H,28,33)(H,29,30,31)
comment: Belumosudil (KD025) is an oral and selective inhbitor of Rho associated coiled-coil containing protein kinase 2 (ROCK2) <Reference id=33040/>, with clinical anti-inflammatory/immunomodulatory activity.
iupac name: 2-[3-[4-(1H-indazol-5-ylamino)quinazolin-2-yl]phenoxy]-N-propan-2-ylacetamide
xref: CHEMBL2005186
synonym: KD025
synonym: SLx-2119
synonym: SLx 2119
synonym: SLx2119
synonym: KD-025
synonym: Rezurock®
approved: t
ligand name: belumosudil
type: SyntheticOrganicLigand

TK05
in ch i key: GRDDFJXOEAJYCT-UHFFFAOYSA-N
in ch i: InChI=1S/C31H25ClN2O5/c1-39-25-12-4-20(5-13-25)29(35)26-14-6-21(16-27(26)31(37)38)30(36)28-15-11-24(17-33-28)34(18-19-2-3-19)23-9-7-22(32)8-10-23/h4-17,19H,2-3,18H2,1H3,(H,37,38)
comment: TK05 is the most potent of three selective leukotriene C4 synthase (LTC4S) inhibitors reported in <Reference id=32998/>, and is one of the compounds calimed in patent WO2011110824 <Reference id=33007/>. LTC4S inhibitors have clinical potential for treating respiratory and/or inflammatory diseases, given LTC4S' pivotal role in the production of pro-inflammatory and bronchoconstricting cysteinyl leukotrienes <Reference id=33006/>.
iupac name: 5-[5-[4-chloro-N-(cyclopropylmethyl)anilino]pyridine-2-carbonyl]-2-(4-methoxybenzoyl)benzoic acid
approved: f
ligand name: TK05
type: SyntheticOrganicLigand

example 36 [WO2016177845]
in ch i key: FQHWQFIPEVBFKT-UHFFFAOYSA-N
in ch i: InChI=1S/C27H26N2O4/c1-33-23-11-18(13-28-25(23)26(30)20-12-21(20)27(31)32)29(14-15-5-6-15)22-10-9-17-8-7-16-3-2-4-19(22)24(16)17/h2-4,9-11,13,15,20-21H,5-8,12,14H2,1H3,(H,31,32)
comment: Example 36 is one of a number of leukotriene C4 synthase (LTC4S) inhibitors claimed in AstraZeneca patent WO2016177845 <Reference id=32997/>, particularly for the treatment of respiratory diseases and inflammation. In support of this enzyme as a drug target, a paper by Kleinschmidt et al. (2015) <Reference id=32998/> demonstrates that LTC4S inhibitors block leukotriene C4 and cys-LT synthesis in vitro and in vivo, but note that their inhibitors are of quite different structure compared to example 36.
iupac name: 2-[5-[cyclopropylmethyl(1,2-dihydroacenaphthylen-5-yl)amino]-3-methoxypyridine-2-carbonyl]cyclopropane-1-carboxylic acid
approved: f
ligand name: example 36 [WO2016177845]
type: SyntheticOrganicLigand

GSK2982772
in ch i key: LYPAFUINURXJSG-AWEZNQCLSA-N
in ch i: InChI=1S/C20H19N5O3/c1-25-15-9-5-6-10-16(15)28-12-14(20(25)27)21-19(26)18-22-17(23-24-18)11-13-7-3-2-4-8-13/h2-10,14H,11-12H2,1H3,(H,21,26)(H,22,23,24)/t14-/m0/s1
comment: GSK2982772 is a first-in-class clinical candidate RIPK1 inhibitor, with anti-inflammatory potential <Reference id=32994/>. X-ray structure of co-crystals shows GSK2982772 in a Type III-like kinase inhibitor position.
iupac name: 5-benzyl-N-[(3S)-5-methyl-4-oxo-2,3-dihydro-1,5-benzoxazepin-3-yl]-1H-1,2,4-triazole-3-carboxamide
synonym: compound 5 [PMID: 28151659]
approved: f
ligand name: GSK2982772
type: SyntheticOrganicLigand

dodecyl-thiophosphate
canonical SMILES: CCCCCCCCCCCCOP(=S)(O)O
isomeric SMILES: CCCCCCCCCCCCOP(=S)(O)O
in ch i key: ISWBBUXCFWZBKC-UHFFFAOYSA-N
in ch i: InChI=1S/C12H27O3PS/c1-2-3-4-5-6-7-8-9-10-11-12-15-16(13,14)17/h2-12H2,1H3,(H2,13,14,17)
iupac name: dodecoxy-dihydroxy-sulfanylidenephosphorane
xref: CHEMBL191365
approved: f
ligand name: dodecyl-thiophosphate
type: SyntheticOrganicLigand

nitrosoprodenafil
in ch i key: BNIFBESUYAAZKT-UHFFFAOYSA-N
in ch i: InChI=1S/C28H36N8O5S2/c1-7-9-21-24-25(36(6)33-21)27(41-28-29-15-23(42-28)35(5)34-37)32-26(31-24)20-14-18(10-11-22(20)40-8-2)43(38,39)19-12-16(3)30-17(4)13-19/h10-11,14-17,19,30H,7-9,12-13H2,1-6H3
comment: Nitrosoprodenafil is a novel nitrosated analogue of the PDE5 inhibitor <Ligand id=4743/>, that acts as a prodrug releasing aildenafil (methisosildenafil; PubChem CID 16721107) and <Ligand id=2509/> <Reference id=32974/>. NO-induced effects on vasodilation are synergistic with inhibition of PDE5 action. This type of compound has been avoided by conventional pharmaceutical companies because of the serious risk of causing a life-threatening drop in blood pressure, and because of the hepatotoxicity of nitrosamines.
iupac name: N-[2-[5-[5-(2,6-dimethylpiperidin-4-yl)sulfonyl-2-ethoxyphenyl]-1-methyl-3-propylpyrazolo[4,3-d]pyrimidin-7-yl]oxy-1,3-thiazol-5-yl]-N-methylnitrous amide
approved: f
ligand name: nitrosoprodenafil
type: SyntheticOrganicLigand

naproxcinod
canonical SMILES: COc1ccc2c(c1)ccc(c2)C(C(=O)OCCCCO[N+](=O)[O-])C
in ch i key: AKFJWRDCWYYTIG-ZDUSSCGKSA-N
in ch i: InChI=1S/C18H21NO6/c1-13(18(20)24-9-3-4-10-25-19(21)22)14-5-6-16-12-17(23-2)8-7-15(16)11-14/h5-8,11-13H,3-4,9-10H2,1-2H3/t13-/m0/s1
comment: Naproxcinod is a NO-donating <Ligand id=5230/> analogue prodrug. It is the first in a new class of anti-inflammatory and analgesic drugs known as cyclooxygenase-inhibiting nitric oxide donors (CINODs) <Reference id=32947/>, that are designed to lessen the gastrointestinal (and cardiovascular) side-effects of traditional NSAIDs. The NO released by the prodrug mediates this beneficial effect.
iupac name: 4-nitrooxybutyl (2S)-2-(6-methoxynaphthalen-2-yl)propanoate
xref: CHEMBL2103831
synonym: HCT-3012
synonym: HCT3012
synonym: HCT 3012
synonym: AZD-3582
synonym: AZD 3582
synonym: AZD3582
synonym: NO-naproxen
approved: f
ligand name: naproxcinod
type: SyntheticOrganicLigand

compound 1e [PMID: 27285276]
canonical SMILES: Clc1ccc(cc1)C=NNC(=O)c1ccccc1
isomeric SMILES: Clc1ccc(cc1)/C=N/NC(=O)c1ccccc1
in ch i key: YJGPDMQKIPQVLX-MHWRWJLKSA-N
in ch i: InChI=1S/C14H11ClN2O/c15-13-8-6-11(7-9-13)10-16-17-14(18)12-4-2-1-3-5-12/h1-10H,(H,17,18)/b16-10+
comment: Compound 1e [PMID: 27285276] is a cathepsin H inhibitor <Reference id=32910/>.
iupac name: N-[(4-chlorophenyl)methylideneamino]benzamide
xref: CHEMBL2235152
approved: f
ligand name: compound 1e [PMID: 27285276]
type: SyntheticOrganicLigand

prexasertib
canonical SMILES: NCCCOc1cccc(c1c1[nH]nc(c1)Nc1cnc(cn1)C#N)OC
isomeric SMILES: NCCCOc1cccc(c1c1[nH]nc(c1)Nc1cnc(cn1)C#N)OC
in ch i key: DOTGPNHGTYJDEP-UHFFFAOYSA-N
in ch i: InChI=1S/C18H19N7O2/c1-26-14-4-2-5-15(27-7-3-6-19)18(14)13-8-16(25-24-13)23-17-11-21-12(9-20)10-22-17/h2,4-5,8,10-11H,3,6-7,19H2,1H3,(H2,22,23,24,25)
comment: Prexasertib (LY2606368), an investigational small molecule checkpoint kinase 1 (CHK1) inhibitor <Reference id=32905/> that exhibits anti-tumour activity in preclinical models of pediatric cancer.
iupac name: 5-[[5-[2-(3-aminopropoxy)-6-methoxyphenyl]-1H-pyrazol-3-yl]amino]pyrazine-2-carbonitrile
xref: CHEMBL3544911
synonym: LY2606368
approved: f
ligand name: prexasertib
type: SyntheticOrganicLigand

GNF362
in ch i key: VNTCGXMLDSKOKN-OAHLLOKOSA-N
in ch i: InChI=1S/C22H21F3N6/c1-15-13-30(8-9-31(15)20-7-6-19(12-27-20)22(23,24)25)14-18-11-28-29-21(18)17-4-2-16(10-26)3-5-17/h2-7,11-12,15H,8-9,13-14H2,1H3,(H,28,29)/t15-/m1/s1
comment: GNF362 is a non-selective inhibitor of all three IP3 kinases <Reference id=32903/> and is one of the structures claimed in patent US20090306039 <Reference id=32904/>.
iupac name: 4-[4-[[(3R)-3-methyl-4-[5-(trifluoromethyl)pyridin-2-yl]piperazin-1-yl]methyl]-1H-pyrazol-5-yl]benzonitrile
synonym: example 71 [US20090306039]
approved: f
ligand name: GNF362
type: SyntheticOrganicLigand

mizagliflozin
in ch i key: LREHMKLEOJAVMQ-TXKDOCKMSA-N
in ch i: InChI=1S/C28H44N4O8/c1-15(2)21-19(25(32-31-21)40-26-24(36)23(35)22(34)20(13-33)39-26)12-17-7-8-18(11-16(17)3)38-10-6-9-30-14-28(4,5)27(29)37/h7-8,11,15,20,22-24,26,30,33-36H,6,9-10,12-14H2,1-5H3,(H2,29,37)(H,31,32)/t20-,22-,23+,24-,26+/m1/s1
comment: A novel selective sodium glucose co-transporter 1 (SGLT1) inhibitor, exhibits potential in the amelioration of chronic constipation.
synonym: DSP-3235
approved: f
ligand name: mizagliflozin
type: SyntheticOrganicLigand

TP-064
in ch i key: VUIITYLFSAXKIQ-UHFFFAOYSA-N
in ch i: InChI=1S/C28H34N4O2/c1-29-15-18-32-16-12-23(13-17-32)27-19-22(11-14-30-27)21-31(2)28(33)24-7-6-10-26(20-24)34-25-8-4-3-5-9-25/h3-11,14,19-20,23,29H,12-13,15-18,21H2,1-2H3
comment: TP-064 is a potent, selective and cell active chemical probe for PRMT4 (officially known as coactivator associated arginine methyltransferase 1; CARM1) <Reference id=32733/>. It is one of the chemical tools in the Structural Genomics Consortium's Epigenetic Probes Collection and was developed in collaboration with Takeda.
iupac name: N-methyl-N-[[2-[1-[2-(methylamino)ethyl]piperidin-4-yl]pyridin-4-yl]methyl]-3-phenoxybenzamide
synonym: TP 064
approved: f
ligand name: TP-064
type: SyntheticOrganicLigand

NS6180
canonical SMILES: O=C1CSc2c(N1Cc1cccc(c1)C(F)(F)F)cccc2
isomeric SMILES: O=C1CSc2c(N1Cc1cccc(c1)C(F)(F)F)cccc2
in ch i key: ZUIJXKLTUFCDGO-UHFFFAOYSA-N
in ch i: InChI=1S/C16H12F3NOS/c17-16(18,19)12-5-3-4-11(8-12)9-20-13-6-1-2-7-14(13)22-10-15(20)21/h1-8H,9-10H2
comment: NS6180 is a KCa3.1 channel inhibitor. It prevents T-cell activation and inflammation in a rat model of inflammatory bowel disease.
iupac name: 4-[[3-(trifluoromethyl)phenyl]methyl]-1,4-benzothiazin-3-one
approved: f
ligand name: NS6180
type: SyntheticOrganicLigand

NF778
in ch i key: RLZIFZVDVFDJNF-UHFFFAOYSA-N
comment: NF778 is a P2X2 receptor antagonist <Reference id=32893/>. Note that we show the salt (Na) stripped structure, but strictly NF778 is the sodium salt.
approved: f
ligand name: NF778
type: SyntheticOrganicLigand

NF770
in ch i key: OVDXRPYTXUZANY-UHFFFAOYSA-N
comment: NF770 is a P2X2 receptor antagonist <Reference id=32893/>. Note that we show the salt (Na) stripped structure, but strictly NF770 is the tetra sodium salt shown in PubChem CID 53310473. This structure matches example 8b in patent US20130338178 <Reference id=32900/> claiming <Ligand id=1728/> derivatives as sirtuin modulators.
iupac name: 5-methoxy-3-[[3-[[3-[[3-[[5-[(8-methoxy-3,6-disulfonaphthalen-2-yl)carbamoyl]-2-methylphenyl]carbamoyl]phenyl]carbamoylamino]benzoyl]amino]-4-methylbenzoyl]amino]naphthalene-2,7-disulfonic acid
approved: f
ligand name: NF770
type: SyntheticOrganicLigand

GSK2656157
in ch i key: PRWSIEBRGXYXAJ-UHFFFAOYSA-N
in ch i: InChI=1S/C23H21FN6O/c1-13-4-3-5-14(28-13)10-19(31)30-9-8-16-18(30)7-6-15(21(16)24)17-11-29(2)23-20(17)22(25)26-12-27-23/h3-7,11-12H,8-10H2,1-2H3,(H2,25,26,27)
comment: GSK2656157 is an optimised, ATP-competitive inhibitor of protein kinase R (PKR)-like endoplasmic reticulum kinase (PERK), designed using the structural scaffold of <Ligand id=6740/> <Reference id=32898/>. Preclinical evaluation is reported in <Reference id=32899/>.
iupac name: 1-[5-(4-amino-7-methylpyrrolo[2,3-d]pyrimidin-5-yl)-4-fluoro-2,3-dihydroindol-1-yl]-2-(6-methylpyridin-2-yl)ethanone
xref: CHEMBL2441340
synonym: GSK-2656157
synonym: compound 6 [PMID: 24900593]
approved: f
ligand name: GSK2656157
type: SyntheticOrganicLigand

BX-430
canonical SMILES: O=C(Nc1c(Br)cc(cc1Br)C(C)C)Nc1cccnc1
isomeric SMILES: O=C(Nc1c(Br)cc(cc1Br)C(C)C)Nc1cccnc1
in ch i key: JFNKIJKRXKPQCC-UHFFFAOYSA-N
in ch i: InChI=1S/C15H15Br2N3O/c1-9(2)10-6-12(16)14(13(17)7-10)20-15(21)19-11-4-3-5-18-8-11/h3-9H,1-2H3,(H2,19,20,21)
comment: BX-430 is a selective allosteric modulator of the human P2X4 receptor <Reference id=32895/>.
iupac name: 1-(2,6-dibromo-4-propan-2-ylphenyl)-3-pyridin-3-ylurea
xref: CHEMBL1532400
synonym: BX430
approved: f
ligand name: BX-430
type: SyntheticOrganicLigand

PSB-12062
in ch i key: DHZNMEIBMACSFH-UHFFFAOYSA-N
in ch i: InChI=1S/C19H15NO3S/c1-14-10-12-15(13-11-14)24(21,22)20-16-6-2-4-8-18(16)23-19-9-5-3-7-17(19)20/h2-13H,1H3
comment: PSB-12062 is a P2X4 receptor antagonist with an allosteric mode of action <Reference id=32894/>.
iupac name: 10-(4-methylphenyl)sulfonylphenoxazine
xref: CHEMBL2180160
synonym: 10-tosyl-10H-phenoxazine
synonym: compound 21 [PMID: 23075067]
approved: f
ligand name: PSB-12062
type: SyntheticOrganicLigand

5-BDBD
canonical SMILES: Brc1cccc(c1)C1=NCC(=O)Nc2c1oc1c2cccc1
isomeric SMILES: Brc1cccc(c1)C1=NCC(=O)Nc2c1oc1c2cccc1
in ch i key: NKYMVQPXXTZHSF-UHFFFAOYSA-N
in ch i: InChI=1S/C17H11BrN2O2/c18-11-5-3-4-10(8-11)15-17-16(20-14(21)9-19-15)12-6-1-2-7-13(12)22-17/h1-8H,9H2,(H,20,21)
comment: 5-BDBD is a potent P2X4 receptor antagonist <Reference id=21963/><Reference id=32893/>.
iupac name: 5-(3-bromophenyl)-1,3-dihydro-[1]benzofuro[3,2-e][1,4]diazepin-2-one
xref: CHEMBL2180179
approved: f
ligand name: 5-BDBD
type: SyntheticOrganicLigand

PSB-10211
in ch i key: BLCUJFVIEUPNOP-UHFFFAOYSA-N
comment: PSB-10211 is a potent competitive antagonist of the P2X2 receptor <Reference id=32887/>. We show the structure of the parent molecule. The sodium salt may be used experimentally (PubChem CID 53308118).
iupac name: 1-amino-4-[3-[(4,6-dichloro-1,3,5-triazin-2-yl)amino]anilino]-9,10-dioxoanthracene-2-sulfonic acid
xref: CHEMBL1741085
synonym: compound 63 [PMID: 21207957]
approved: f
ligand name: PSB-10211
type: SyntheticOrganicLigand

AF-906
in ch i key: PAYROHWFGZADBR-UHFFFAOYSA-N
in ch i: InChI=1S/C17H23IN4O4/c1-9(2)11-4-14(25-3)12(18)5-13(11)26-15-6-20-17(22-16(15)19)21-10(7-23)8-24/h4-6,9-10,23-24H,7-8H2,1-3H3,(H3,19,20,21,22)
comment: AF-906 is a potent and selective dual P2X3/P2X2/3 diaminopyrimidine antagonist <Reference id=32886/>.
iupac name: 2-[[4-amino-5-(5-iodo-4-methoxy-2-propan-2-ylphenoxy)pyrimidin-2-yl]amino]propane-1,3-diol
xref: CHEMBL494161
synonym: Ro-51
synonym: Ro 51
synonym: compound 128 [PMID: 26686393]
approved: f
ligand name: AF-906
type: SyntheticOrganicLigand

atracurium
in ch i key: YXSLJKQTIDHPOT-UHFFFAOYSA-N
in ch i: InChI=1S/C53H72N2O12/c1-54(22-18-38-32-48(62-7)50(64-9)34-40(38)42(54)28-36-14-16-44(58-3)46(30-36)60-5)24-20-52(56)66-26-12-11-13-27-67-53(57)21-25-55(2)23-19-39-33-49(63-8)51(65-10)35-41(39)43(55)29-37-15-17-45(59-4)47(31-37)61-6/h14-17,30-35,42-43H,11-13,18-29H2,1-10H3/q+2
comment: Atracurium (besylate) is a intermediate-duration non-depolarizing neuromuscular blocking agent, delivered by bolus injection in to a vein. It is a complex molecule with potential to exist as multiple stereoisomers.The INN for this drug stipulates the besylate salt, represented in PubChem CID 47320. We show the structure for the parent molecule, with no specified stereochemistry.
iupac name: 5-[3-[1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy-2-methyl-3,4-dihydro-1H-isoquinolin-2-ium-2-yl]propanoyloxy]pentyl 3-[1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy-2-methyl-3,4-dihydro-1H-isoquinolin-2-ium-2-yl]propanoate
xref: CHEMBL1360
synonym: atracurium besilate
synonym: Tracrium®
synonym: atracurium dibesylate
synonym: BW 33A
approved: t
ligand name: atracurium
type: SyntheticOrganicLigand

otenaproxesul
in ch i key: YCNMAPLPQYQJFC-ZDUSSCGKSA-N
in ch i: InChI=1S/C21H19NO3S/c1-13(21(23)25-18-8-5-14(6-9-18)20(22)26)15-3-4-17-12-19(24-2)10-7-16(17)11-15/h3-13H,1-2H3,(H2,22,26)/t13-/m0/s1
comment: Otenaproxesul (ATB-346) is a novel, orally administered, gastrointestinal-sparing hydrogen sulfide (H2S)-releasing analgesic and anti-inflammatory drug in clinical trials for osteoarthritis <Reference id=37790/>. Structurally it comprises an H2S-releasing moiety covalently linked to a NSAID (<Ligand id=5230/>). H2S-releasing NSAIDs are in development for their potential analgesic, anti-inflammatory, cytoprotective and chemopreventative properties <Reference id=32744/><Reference id=32751/><Reference id=32746/><Reference id=32747/><Reference id=34281/><Reference id=33731/>.
synonym: ATB-346
synonym: ATB346
synonym: ATB-346, (S)-
synonym: ATB 346
approved: f
ligand name: otenaproxesul
type: SyntheticOrganicLigand

DU172
in ch i key: KAJVJPLKXGLLDA-UHFFFAOYSA-N
in ch i: InChI=1S/C24H30FN5O5S/c1-2-14-30-23(32)19-21(28-20(27-19)16-7-4-3-5-8-16)29(24(30)33)15-6-13-26-22(31)17-9-11-18(12-10-17)36(25,34)35/h9-12,16H,2-8,13-15H2,1H3,(H,26,31)(H,27,28)
comment: Selective covalent A1 receptor antagonist.
iupac name: 4-[3-(8-cyclohexyl-2,6-dioxo-1-propyl-7H-purin-3-yl)propylcarbamoyl]benzenesulfonyl fluoride
approved: f
ligand name: DU172
type: SyntheticOrganicLigand

MS049
canonical SMILES: CNCCN1CCC(CC1)OCc1ccccc1
isomeric SMILES: CNCCN1CCC(CC1)OCc1ccccc1
in ch i key: HBOJWAYLSJLULG-UHFFFAOYSA-N
in ch i: InChI=1S/C15H24N2O/c1-16-9-12-17-10-7-15(8-11-17)18-13-14-5-3-2-4-6-14/h2-6,15-16H,7-13H2,1H3
comment: MS049 is a potent and selective dual inhibitor of PRMT4 and PRMT6 <Reference id=32735/><Reference id=32734/>, developed in a collaboration between the Structural Genomics Consortium and the Icahn School of Medicine at Mount Sinai. It is active in cellular assays. It is one of the chemical tools in the SGC's Epigenetic Probes Collection.
iupac name: N-methyl-2-(4-phenylmethoxypiperidin-1-yl)ethanamine
synonym: compound 17 [PMID: 27584694]
approved: f
ligand name: MS049
type: SyntheticOrganicLigand

LLY-283
canonical SMILES: OC(C1OC(C(C1O)O)n1ccc2c1ncnc2N)c1ccccc1
in ch i key: WWOOWAHTEXIWBO-QFRSUPTLSA-N
in ch i: InChI=1S/C17H18N4O4/c18-15-10-6-7-21(16(10)20-8-19-15)17-13(24)12(23)14(25-17)11(22)9-4-2-1-3-5-9/h1-8,11-14,17,22-24H,(H2,18,19,20)/t11-,12+,13-,14-,17-/m1/s1
comment: LLY-283 is a potent and selective SAM-competitive chemical probe for PRMT5 (protein arginine methyltransferase 5) developed in a collaboration between Eli Lilly and the Structural Genomics Consortium <Reference id=32732/>. It is one of the chemical tools in the SGC's Epigenetic Probes Collection.
iupac name: (2R,3R,4S,5R)-2-(4-aminopyrrolo[2,3-d]pyrimidin-7-yl)-5-[(R)-hydroxy(phenyl)methyl]oxolane-3,4-diol
approved: f
ligand name: LLY-283
type: SyntheticOrganicLigand

MI-503
in ch i key: DETOMBLLEOZTMZ-UHFFFAOYSA-N
in ch i: InChI=1S/C28H27F3N8S/c1-17-19(2-3-25-23(17)8-21(11-32)39(25)14-18-12-35-36-13-18)15-38-6-4-20(5-7-38)37-26-24-9-22(10-28(29,30)31)40-27(24)34-16-33-26/h2-3,8-9,12-13,16,20H,4-7,10,14-15H2,1H3,(H,35,36)(H,33,34,37)
comment: MI-503 inhibits the interaction between MLL oncoproteins (re-arranged lysine methyltransferase 2A; KMT2A; a.k.a. MLL1) and the tumour suppressor protein menin (MEN1, O00255), by binding directly to MLL binding site on menin <Reference id=32731/>. MI-503 is active in vivo, exhibiting selective antiproliferative effects on cells harbouring MLL rearrangements. It represents a highly optimised molecular scaffold for clinical lead identification in the development of drugs for the treatment of aggressive MLL-rearranged leukemias.
iupac name: 4-methyl-1-(1H-pyrazol-4-ylmethyl)-5-[[4-[[6-(2,2,2-trifluoroethyl)thieno[2,3-d]pyrimidin-4-yl]amino]piperidin-1-yl]methyl]indole-2-carbonitrile
approved: f
ligand name: MI-503
type: SyntheticOrganicLigand

A-395
in ch i key: REVJNSVNICWODC-KIDMSAQOSA-N
in ch i: InChI=1S/C26H35FN4O2S/c1-28(2)25-18-30(24-12-9-20-5-4-6-23(27)26(20)24)17-22(25)19-7-10-21(11-8-19)29-13-15-31(16-14-29)34(3,32)33/h4-8,10-11,22,24-25H,9,12-18H2,1-3H3/t22-,24?,25+/m1/s1
comment: A-395 potently binds the embryonic ectoderm development protein (EED) <Reference id=32730/>, a protein with a scaffolding function and an H3K27me3-binding function. A-395 inhibits this latter function by binding in the H3K27me3-binding pocket of EED. This action prevents allosteric activation of the catalytic activity of the EED-containing polycomb repressive complex 2 (PRC2). A-395 is one of the chemical tools in the Structural Genomics Consortium's Epigenetic Probes Library. and was developed in collaboration with Abbvie.
iupac name: (3R,4S)-1-(7-fluoro-2,3-dihydro-1H-inden-1-yl)-N,N-dimethyl-4-[4-(4-methylsulfonylpiperazin-1-yl)phenyl]pyrrolidin-3-amine
approved: f
ligand name: A-395
type: SyntheticOrganicLigand

BAY-299
in ch i key: OFWWWKWUCDUISA-UHFFFAOYSA-N
in ch i: InChI=1S/C25H23N3O4/c1-14-12-20-21(27(3)25(32)26(20)2)13-19(14)28-23(30)17-8-4-7-16-15(6-5-11-29)9-10-18(22(16)17)24(28)31/h4,7-10,12-13,29H,5-6,11H2,1-3H3
comment: BAY-299 is a potent and selective inhibitor of BRPF2 (a.k.a. BRD1) and the second bromodomain of TAF1. It is >30-fold selective for BRPF2 over BRPF1 and -3. It is one of the chemical tools in the Structural Genomics Consortium's Epigenetic Probes Library and was developed in collaboration with Bayer.
iupac name: 6-(3-hydroxypropyl)-2-(1,3,6-trimethyl-2-oxobenzimidazol-5-yl)benzo[de]isoquinoline-1,3-dione
approved: f
ligand name: BAY-299
type: SyntheticOrganicLigand

OF-1
in ch i key: YUNQZQREIHWDQT-UHFFFAOYSA-N
comment: OF-1 is a small molecule inhibitor of the bromodomain proteins BRPF1/2/3 and is one of the chemical tools in the Structural Genomics Consortium's Epigenetic Probes Library. BRPF1/2/3 provide the scaffold for the formation of MYST complexes which play essential functions in DNA repair, recombination, replication and activation of transcription.
iupac name: 4-bromo-N-(6-methoxy-1,3-dimethyl-2-oxo-2,3-dihydro-1H-1,3-benzodiazol-5-yl)-2-methylbenzene-1-sulfonamide
synonym: OF 1
approved: f
ligand name: OF-1
type: SyntheticOrganicLigand

TP-472
in ch i key: RPBMXJHQYJLPDN-UHFFFAOYSA-N
in ch i: InChI=1S/C20H19N3O2/c1-12-4-5-14(20(25)22-15-6-7-15)10-16(12)17-11-18(13(2)24)23-9-3-8-21-19(17)23/h3-5,8-11,15H,6-7H2,1-2H3,(H,22,25)
comment: TP-472 is a potent BRD9/7 inhibitor tool compound that is cell permeable and active in vivo. TP-472 is one of the chemical tools in the Structural Genomics Consortium's Epigenetic Probes Library.
iupac name: 3-{6-acetylpyrrolo[1,2-a]pyrimidin-8-yl}-N-cyclopropyl-4-methylbenzamide
approved: f
ligand name: TP-472
type: SyntheticOrganicLigand

GSK8814
in ch i key: YDPMMWAOCCOULO-JBRSBNLGSA-N
in ch i: InChI=1S/C28H35F2N5O3/c1-16-8-19(11-31-10-16)21-12-33-26(24-20(21)9-17(2)27(36)35-24)34-25-22(37-3)13-32-14-23(25)38-15-18-4-6-28(29,30)7-5-18/h8-12,18,22-23,25,32H,4-7,13-15H2,1-3H3,(H,33,34)(H,35,36)/t22-,23+,25+/m0/s1
comment: GSK8814 is a chemical probe for the ATAD2/2B bromodomain <Reference id=32725/> and is available via the Stuctural Genomics Consortium's chemical probe dissemination program. Click here to link to the SGC's full list of epigenetics probes.
iupac name: 8-(((3R,4R,5S)-3-((4,4-difluorocyclohexyl)methoxy)-5-methoxypiperidin-4-yl)amino)-3-methyl-5-(5-methylpyridin-3-yl)-1,7-naphthyridin-2(1H)-one
approved: f
ligand name: GSK8814
type: SyntheticOrganicLigand

N-methyl-2-pyrrolidone
canonical SMILES: O=C1CCCN1C
isomeric SMILES: O=C1CCCN1C
in ch i key: SECXISVLQFMRJM-UHFFFAOYSA-N
in ch i: InChI=1S/C5H9NO/c1-6-4-2-3-5(6)7/h2-4H2,1H3
comment: NMP is a common solvent and drug vehicle. More recently it has been identified as a candidate bromodomain ligand with antineoplastic and immunomodulatory activity <Reference id=32719/>. Mechanistically it appears to be a low-affinity, broad-spectrum acetyllysine mimetic, but with apparent comparable ligand efficiency to that of larger rationally developed compounds such as <Ligand id=7511/> because of its very low molecular weight.
iupac name: 1-methylpyrrolidin-2-one
synonym: N-methyl-pyrrolidone
approved: f
ligand name: N-methyl-2-pyrrolidone
type: SyntheticOrganicLigand

analog 3 [Vlattas et al., 1996]
canonical SMILES: CN(CC(=O)O)CCOP(=O)(OP(=O)(O)O)O
isomeric SMILES: CN(CC(=O)O)CCOP(=O)(OP(=O)(O)O)O
in ch i key: YERUUUBBRAPJND-UHFFFAOYSA-N
in ch i: InChI=1S/C5H13NO9P2/c1-6(4-5(7)8)2-3-14-17(12,13)15-16(9,10)11/h2-4H2,1H3,(H,7,8)(H,12,13)(H2,9,10,11)
comment: This ligand is referred to as analog 3 in the reference <Reference id=26365/>, which has no available PMID.
iupac name: 2-[2-[hydroxy(phosphonooxy)phosphoryl]oxyethyl-methylamino]acetic acid
xref: CHEMBL1160330
approved: f
ligand name: analog 3 [Vlattas et al., 1996]
type: SyntheticOrganicLigand

CHMFL-BTK-11
in ch i key: AANOKQLITQDWQD-UHFFFAOYSA-N
in ch i: InChI=1S/C25H21N5O2/c1-3-23(31)28-22-14-19(7-5-16(22)2)30-24(32)10-6-17-15-26-21-9-8-18(13-20(21)25(17)30)29-12-4-11-27-29/h3-5,7-9,11-15H,1,6,10H2,2H3,(H,28,31)
comment: CHMFL-BTK-11 exerts its inhibitory efficacy through a covalent bond with BTK Cys481. Should be a pharmacological tool for BTK mediated signaling in rheumatoid arthritis <Reference id=32693/>.
iupac name: N-{2-methyl-5-[2-oxo-9-(1H-pyrazol-1-yl)-1H,2H,3H,4H-benzo[h]1,6-naphthyridin-1-yl]phenyl}prop-2-enamide
approved: f
ligand name: CHMFL-BTK-11
type: SyntheticOrganicLigand

L-arginine
canonical SMILES: OC(=O)C(CCCN=C(N)N)N
isomeric SMILES: OC(=O)[C@H](CCCN=C(N)N)N
in ch i key: ODKSFYDXXFIFQN-BYPYZUCNSA-N
in ch i: InChI=1S/C6H14N4O2/c7-4(5(11)12)2-1-3-10-6(8)9/h4H,1-3,7H2,(H,11,12)(H4,8,9,10)/t4-/m0/s1
iupac name: (2S)-2-amino-5-(diaminomethylideneamino)pentanoic acid
xref: CHEMBL1485
synonym: Argamine
synonym: Argivene
synonym: Detoxargin
synonym: Levargin
synonym: Minophagen A
synonym: R-Gene 10
approved: f
ligand name: L-arginine
type: MetaboliteLigand

SRT2104
in ch i key: LAMQVIQMVKWXOC-UHFFFAOYSA-N
in ch i: InChI=1S/C26H24N6O2S2/c1-17-23(36-25(28-17)18-5-4-8-27-13-18)24(33)29-21-7-3-2-6-20(21)22-15-32-19(16-35-26(32)30-22)14-31-9-11-34-12-10-31/h2-8,13,15-16H,9-12,14H2,1H3,(H,29,33)
comment: SRT2104 (GSK2245840) is an investigational, selective and orally available SIRT1 activator <Reference id=32675/><Reference id=33311/>.
iupac name: 4-methyl-N-[2-[3-(morpholin-4-ylmethyl)imidazo[2,1-b][1,3]thiazol-6-yl]phenyl]-2-pyridin-3-yl-1,3-thiazole-5-carboxamide
synonym: compound 4 [Ng et al., 2013]
synonym: GSK2245840
synonym: SRT-2104
approved: f
ligand name: SRT2104
type: SyntheticOrganicLigand

SIRT1 activator 3
in ch i key: VNOFYGGJZCEPAH-UHFFFAOYSA-N
in ch i: InChI=1S/C20H25N5O2/c1-27-12-6-11-25-18(21)16(20(26)22-13-7-2-3-8-13)17-19(25)24-15-10-5-4-9-14(15)23-17/h4-5,9-10,13H,2-3,6-8,11-12,21H2,1H3,(H,22,26)
comment: A selective SIRT1 activator for use as a biological tool <Reference id=32683/>.
iupac name: 2-amino-N-cyclopentyl-1-(3-methoxypropyl)pyrrolo[3,2-b]quinoxaline-3-carboxamide
synonym: SA3
synonym: SA-3
approved: f
ligand name: SIRT1 activator 3
type: SyntheticOrganicLigand

MLKL compound 1
in ch i key: SNRUTMWCDZHKKM-UHFFFAOYSA-N
comment: This small molecule acts as an inhibitor of the activity of mixed lineage kinase domain like pseudokinase MLKL. The compound binds the nucleotide binding site within the MLKL pseudokinase domain and reduces MLKL translocation to the cell membrane, which has the effect of preventing MLKL-driven necroptosis (necroptosis being a form of regulated inflammatory cell death <Reference id=32668/>) <Reference id=32665/>. This effect is driven by blocking the conformational change in the N-terminal four-helix bundle (4HB) domain of the protein caused by nucleotide binding that is required for membrane translocation and killing activity. This compound was originally identified as a nanomolar potency inhibitor of VEGFR2 tyrosine kinase <Reference id=32666/>, but note that inhibition of VEGFR2 by another VEGFR2 inhibitor (<Ligand id=5711/>) does not prevent necroptosis, suggesting a direct role for MLKL in this form of cell death, and also demonstrates that targeting the nucleotide binding site of pseudokinases is a novel strategy for modulating signal transduction. In summary, MLKL compound 1 provides a useful tool for investigating necroptosis.
xref: CHEMBL188381
synonym: GW806742X
synonym: compound 23 [PMID: 15990302]
approved: f
ligand name: MLKL compound 1
type: SyntheticOrganicLigand

solabegron
in ch i key: LLDXOPKUNJTIRF-QFIPXVFZSA-N
in ch i: InChI=1S/C23H23ClN2O3/c24-20-8-2-6-18(13-20)22(27)15-25-10-11-26-21-9-3-5-17(14-21)16-4-1-7-19(12-16)23(28)29/h1-9,12-14,22,25-27H,10-11,15H2,(H,28,29)/t22-/m0/s1
comment: Solabegron (GW427353) is a highly potent and selective β3-adrenoceptor agonist <Reference id=32613/>. β3 agonists (e.g. <Ligand id=7445/> and solabegron) failed to show efficacy for their original clinical indication, obesity/type 2 diabetes, but have been repurposed/repositioned for the treatment of the overactive bladder syndrome <Reference id=32614/>.
iupac name: 3-[3-[2-[[(2R)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]ethylamino]phenyl]benzoic acid
xref: CHEMBL208427
synonym: GW 427353
synonym: GW427353
synonym: GW-427353
synonym: compound 38 [PMID: 16640337]
approved: f
ligand name: solabegron
type: SyntheticOrganicLigand

ACT-389949
in ch i key: PBTWPEDVIMHJEO-UHFFFAOYSA-N
in ch i: InChI=1S/C20H18F2N6O3/c1-11-5-4-6-13(7-11)18-17(24-12(2)31-18)19(29)26-15-8-23-28(27-15)9-16-25-14(10-30-16)20(3,21)22/h4-8,10H,9H2,1-3H3,(H,26,27,29)
comment: ACT-389949 is a novel potent and selective FPR2/ALX agonist <Reference id=32610/>. Results from Phase 1 trials in healthy subjects show that ACT-389949 is well tolerated, but drug potential is hampered by several factors: it causes rapid receptor desensitisation; it elicits only a transient response; biomarker analysis suggests that the response is pro-inflammatory rather than anti-inflammatory <Reference id=32610/>.
iupac name: N-(2-{[4-(1,1-difluoroethyl)-1,3-oxazol-2-yl]methyl}-2H-1,2,3-triazol-4-yl)-2-methyl-5-(3-methylphenyl)-1,3-oxazole-4-carboxamide
approved: f
ligand name: ACT-389949
type: SyntheticOrganicLigand

SB-3CT
canonical SMILES: O=S(=O)(c1ccc(cc1)Oc1ccccc1)CC1SC1
isomeric SMILES: O=S(=O)(c1ccc(cc1)Oc1ccccc1)CC1SC1
in ch i key: LSONWRHLFZYHIN-UHFFFAOYSA-N
in ch i: InChI=1S/C15H14O3S2/c16-20(17,11-14-10-19-14)15-8-6-13(7-9-15)18-12-4-2-1-3-5-12/h1-9,14H,10-11H2
comment: SB-3CT is a dual MMP2/MMP9 inhibitor <Reference id=32568/>.
iupac name: 2-[[4-(phenoxy)phenyl]sulfonylmethyl]thiirane
xref: CHEMBL483857
synonym: inhibitor 1 (Brown et al., 2000)
approved: f
ligand name: SB-3CT
type: SyntheticOrganicLigand

MDP-rhodamine
in ch i key: WIKKPYADGXLQLA-FREYQMBCSA-O
in ch i: InChI=1S/C54H72N8O15S/c1-8-61(9-2)33-17-20-36-40(26-33)76-41-27-34(62(10-3)11-4)18-21-37(41)45(36)35-19-16-32(25-38(35)52(71)72)59-54(78)56-24-14-12-13-15-44(66)74-28-42-47(67)48(46(53(73)77-42)58-31(7)63)75-30(6)51(70)57-29(5)50(69)60-39(49(55)68)22-23-43(64)65/h16-21,25-27,29-30,39,42,46-48,53,67,73H,8-15,22-24,28H2,1-7H3,(H8,55,56,57,58,60,63,64,65,68,69,70,71,72,78)/p+1/t29-,30+,39+,42+,46+,47+,48+,53+/m0/s1
comment: Rhodamine labelled <Ligand id=5024/> (MDP).
synonym: MDP-Hex-Rhodamine B
approved: f
ligand name: MDP-rhodamine
type: SyntheticOrganicLigand

glycyl-sarcosine
canonical SMILES: CN(C(=O)CN)CC(=O)O
isomeric SMILES: CN(C(=O)CN)CC(=O)O
in ch i key: VYAMLSCELQQRAE-UHFFFAOYSA-N
in ch i: InChI=1S/C5H10N2O3/c1-7(3-5(9)10)4(8)2-6/h2-3,6H2,1H3,(H,9,10)
iupac name: 2-[(2-aminoacetyl)-methylamino]acetic acid
xref: CHEMBL175737
synonym: glycylsarcosine
synonym: Gly-Sar
approved: f
ligand name: glycyl-sarcosine
type: PeptideLigand

γ-iE-DAP
in ch i key: QIFGMZZTJRULMA-XLPZGREQSA-N
in ch i: InChI=1S/C12H21N3O7/c13-6(10(17)18)2-1-3-8(12(21)22)15-9(16)5-4-7(14)11(19)20/h6-8H,1-5,13-14H2,(H,15,16)(H,17,18)(H,19,20)(H,21,22)/t6-,7+,8+/m0/s1
comment: An analog of <Ligand id=5021/>.
synonym: Gamma-d-glutamyl-meso-diaminopimelic acid
synonym: Gamma-D-Glu-mDAP
synonym: iE-DAP
synonym: γ-D-glutamyl-meso-diaminopimelic acid
approved: f
ligand name: γ-iE-DAP
type: PeptideLigand

alafosfalin
canonical SMILES: CC(P(=O)(O)O)NC(=O)C(N)C
isomeric SMILES: C[C@@H](P(=O)(O)O)NC(=O)[C@@H](N)C
in ch i key: BHAYDBSYOBONRV-IUYQGCFVSA-N
in ch i: InChI=1S/C5H13N2O4P/c1-3(6)5(8)7-4(2)12(9,10)11/h3-4H,6H2,1-2H3,(H,7,8)(H2,9,10,11)/t3-,4+/m0/s1
comment: Alafosfalin is a phosphonodipeptide with antibacterial and antifungal properties.
iupac name: [(1R)-1-[[(2S)-2-aminopropanoyl]amino]ethyl]phosphonic acid
synonym: alaphosphin
approved: f
ligand name: alafosfalin
type: PeptideLigand

His-Leu-lopinavir
in ch i key: CNRARJITWNMDCM-XGZCXRAPSA-N
in ch i: InChI=1S/C51H70N8O7/c1-33(2)23-40(56-45(60)27-39(52)26-42-30-53-32-55-42)29-47(62)66-44(43(25-38-19-11-8-12-20-38)58-46(61)31-65-49-35(5)15-13-16-36(49)6)28-41(24-37-17-9-7-10-18-37)57-50(63)48(34(3)4)59-22-14-21-54-51(59)64/h7-13,15-20,30,32-34,39-41,43-44,48H,14,21-29,31,52H2,1-6H3,(H,53,55)(H,54,64)(H,56,60)(H,57,63)(H,58,61)/t39?,40?,41-,43-,44-,48-/m0/s1
comment: A histidine based dipeptide prodrug of lopinavir (PubChem CID 92727). Lopinavir is an HIV protease inhibitor used in a fixed-dose combination with <Ligand id=8804/>. It is also an inhibitor of cytochrome P450 CYP3A.
synonym: Histidine-Leucine-Lopinavir
synonym: His-Leu-LPV
approved: f
ligand name: His-Leu-lopinavir
type: SyntheticOrganicLigand

β-Ala-Lys-AMCA
in ch i key: BXZFTTVQAOLWHY-INIZCTEOSA-N
in ch i: InChI=1S/C21H28N4O6/c1-12-14-6-5-13(23)10-17(14)31-21(30)15(12)11-19(27)24-9-3-2-4-16(20(28)29)25-18(26)7-8-22/h5-6,10,16H,2-4,7-9,11,22-23H2,1H3,(H,24,27)(H,25,26)(H,28,29)/t16-/m0/s1
comment: A ﬂuorescent dipeptide.
iupac name: (2S)-6-[[2-(7-amino-4-methyl-2-oxochromen-3-yl)acetyl]amino]-2-(3-aminopropanoylamino)hexanoic acid
synonym: β-alanyl-lysyl-N-7-amino-4-methylcoumarin-3-acetic acid
synonym: Beta-Ala-Lys-N(epsilon)-AMCA
approved: f
ligand name: β-Ala-Lys-AMCA
type: PeptideLigand

diphenyleneiodonium chloride
canonical SMILES: c1ccc2c(c1)[I+]c1c2cccc1.[Cl-]
isomeric SMILES: c1ccc2c(c1)[I+]c1c2cccc1.[Cl-]
in ch i key: FCFZKAVCDNTYID-UHFFFAOYSA-M
in ch i: InChI=1S/C12H8I.ClH/c1-3-7-11-9(5-1)10-6-2-4-8-12(10)13-11;/h1-8H;1H/q+1;/p-1
comment: This ligand is represented in ChEMBL without the chloride by the entry with ID CHEMBL365739.
approved: f
ligand name: diphenyleneiodonium chloride
type: SyntheticOrganicLigand

TCLPA5
in ch i key: BNALUYKEGYUHQC-UHFFFAOYSA-N
in ch i: InChI=1S/C23H23ClN2O3/c1-29-18-9-5-8-17(13-18)26-22(14-21(25-26)23(27)28)16-10-11-19(20(24)12-16)15-6-3-2-4-7-15/h5,8-15H,2-4,6-7H2,1H3,(H,27,28)
comment: TCLPA5 is a selective, non-lipid lysophosphatidic acid 5 (LPA5) receptor selective antagonist <Reference id=32488/>.
xref: CHEMBL2058156
synonym: TC LPA5 4
synonym: compound 4 [PMID: 22801643]
approved: f
ligand name: TCLPA5
type: SyntheticOrganicLigand

ONO-7300243
in ch i key: WGABOZPQOOZAOI-UHFFFAOYSA-N
in ch i: InChI=1S/C28H31NO5/c1-20-25(33-2)17-24(18-26(20)34-3)28(32)29(15-7-10-21-8-5-4-6-9-21)19-23-13-11-22(12-14-23)16-27(30)31/h4-6,8-9,11-14,17-18H,7,10,15-16,19H2,1-3H3,(H,30,31)
comment: ONO-7300243 is a selective lysophosphatidic acid receptor 1 (LPA1) antagonist with favourable in vivo efficacy (reducing intraurethral pressure) in rat models of benign prostatic hyperplasia, which in contrast to the α1-adrenoceptor antagonist <Ligand id=488/> used clinically in this condition, has no effect on blood pressure <Reference id=32485/>.
iupac name: 2-[4-[[(3,5-dimethoxy-4-methylbenzoyl)-(3-phenylpropyl)amino]methyl]phenyl]acetic acid
synonym: compound 17a
approved: f
ligand name: ONO-7300243
type: SyntheticOrganicLigand

BMS-986020
in ch i key: GQBRZBHEPUQRPL-LJQANCHMSA-N
in ch i: InChI=1S/C29H26N2O5/c1-18-25(30-28(34)35-19(2)20-6-4-3-5-7-20)26(36-31-18)23-10-8-21(9-11-23)22-12-14-24(15-13-22)29(16-17-29)27(32)33/h3-15,19H,16-17H2,1-2H3,(H,30,34)(H,32,33)/t19-/m1/s1
comment: BMS-986020 is an investigational lysophosphatidic acid 1 (LPA1) receptor antagonist <Reference id=28706/>. It is claimed as Compound 1-1 in patent WO2010141768 <Reference id=32484/>, and this document contains extensive in vitro characterisation data and records in vivo anti-fibrotic efficacy in various animal models of fibrosis.
iupac name: 1-[4-[4-[3-methyl-4-[[(1R)-1-phenylethoxy]carbonylamino]-1,2-oxazol-5-yl]phenyl]phenyl]cyclopropane-1-carboxylic acid
synonym: am-152
synonym: AP-3152 free acid
synonym: AM152
approved: f
ligand name: BMS-986020
type: SyntheticOrganicLigand

BMS-817399
in ch i key: PTNKPLPRPJERNR-XXBNENTESA-N
in ch i: InChI=1S/C23H35ClN2O4/c1-15(2)19(25-18(27)13-22(5,6)29)20(28)26-12-11-23(30,21(3,4)14-26)16-7-9-17(24)10-8-16/h7-10,15,19,29-30H,11-14H2,1-6H3,(H,25,27)/t19-,23+/m1/s1
comment: BMS-817399 is a selective and orally bioavailable CCR1 receptor antagonist <Reference id=32843/>.
xref: CHEMBL3334824
synonym: compound 29 [PMID: 25101488]
approved: f
ligand name: BMS-817399
type: SyntheticOrganicLigand

A-971432
in ch i key: WAAWETUDFSIYSD-UHFFFAOYSA-N
in ch i: InChI=1S/C18H17Cl2NO3/c19-16-6-3-13(7-17(16)20)11-24-15-4-1-12(2-5-15)8-21-9-14(10-21)18(22)23/h1-7,14H,8-11H2,(H,22,23)
comment: A-971432 is an orally bioavailable selective sphingosine-1-phosphate receptor 5 (S1P5R) agonist, notably with no S1P1R activity. It is compound 29 in <Reference id=32479/> and is claimed in patent WO2010093704 <Reference id=32478/>. A-971432 is suitable for differentiating S1P1 vs. S1P5 biology in vivo. The compound is being investigated for treatment efficacy in neurodegenerative disorders.
iupac name: 1-({4-[(3,4-dichlorophenyl)methoxy]phenyl}methyl)azetidine-3-carboxylic acid
approved: f
ligand name: A-971432
type: SyntheticOrganicLigand

compound 5c [PMID: 27894870]
in ch i key: XDCOYBQVEVSNNB-UHFFFAOYSA-N
in ch i: InChI=1S/C23H21NO2S/c25-22(26)9-4-12-24-15-20-14-19-7-3-8-21(23(19)27-20)18-11-10-16-5-1-2-6-17(16)13-18/h1-3,5-8,10-11,13-14,24H,4,9,12,15H2,(H,25,26)
comment: Compound 5c [PMID: 27894870] is a sphingosine-1-phosphate 4 receptor agonist with favourable selectivity for S1P4R over the other S1P receptors <Reference id=32477/>.
iupac name: 4-({[7-(naphthalen-2-yl)-1-benzothiophen-2-yl]methyl}amino)butanoic acid
approved: f
ligand name: compound 5c [PMID: 27894870]
type: SyntheticOrganicLigand

CYM-5541
canonical SMILES: O=C(N(C1CCCCC1)C1CCCCC1)c1noc(c1)C1CC1
isomeric SMILES: O=C(N(C1CCCCC1)C1CCCCC1)c1noc(c1)C1CC1
in ch i key: NDKGACIWVAOUQH-UHFFFAOYSA-N
in ch i: InChI=1S/C19H28N2O2/c22-19(17-13-18(23-20-17)14-11-12-14)21(15-7-3-1-4-8-15)16-9-5-2-6-10-16/h13-16H,1-12H2
comment: CYM-5541 is a selective sphingosine-1-phosphate 3 receptor (S1P3R) positive allosteric modulator <Reference id=32473/>.
iupac name: N,N-dicyclohexyl-5-cyclopropyl-1,2-oxazole-3-carboxamide
xref: CHEMBL1970071
synonym: CYM5541
synonym: CYM 5541
synonym: ML249
synonym: ML-249
approved: f
ligand name: CYM-5541
type: SyntheticOrganicLigand

SPM-354
in ch i key: WDHXDLFPOPVGGO-IBGZPJMESA-N
comment: SPM-354 is a novel bitopic sphingosine 1-phosphate 3 receptor (SIP3R) antagonist <Reference id=32472/>. SPM-354 competes for binding in both the orthosteric and allosteric sites, as defined by the natural ligand and the selective allosteric S1P3 positive allosteric modulator <Ligand id=9494/>, respectively. SPM-354 is reference example 47 in WO2011004604.
iupac name: [(2S)-2-amino-2-[2-[2-chloro-4-[2-hydroxy-5-(trifluoromethyl)phenyl]sulfanylphenyl]ethyl]pentyl] dihydrogen phosphate
approved: f
ligand name: SPM-354
type: SyntheticOrganicLigand

compound 43 [PMID: 26751273]
in ch i key: BGAJNPLDJJBRHK-UHFFFAOYSA-N
comment: Compound 43 [PMID: 26751273] is an orally active tetrahydropyrazolopyridine sphingosine 1-phosphate receptor 3 (S1P3R)-sparing S1P1R agonist <Reference id=32470/>.
iupac name: 3-[2-[5-(3-chloro-4-propan-2-yloxyphenyl)-1,3,4-thiadiazol-2-yl]-3-methyl-6,7-dihydro-4H-pyrazolo[4,3-c]pyridin-5-yl]propanoic acid
approved: f
ligand name: compound 43 [PMID: 26751273]
type: SyntheticOrganicLigand

amiselimod phosphate
in ch i key: OFRUGVQKZMGHHH-GOSISDBHSA-N
in ch i: InChI=1S/C19H31F3NO6P/c1-2-3-4-5-6-11-28-17-8-7-15(12-16(17)19(20,21)22)9-10-18(23,13-24)14-29-30(25,26)27/h7-8,12,24H,2-6,9-11,13-14,23H2,1H3,(H2,25,26,27)/t18-/m1/s1
comment: Amiselimod phosphate is the active metabolite of <Ligand id=9319/> <Reference id=32464/>. Bioactivity is ascribed to this compound and not to the prodrug.
iupac name: [(2R)-2-amino-4-[4-heptoxy-3-(trifluoromethyl)phenyl]-2-(hydroxymethyl)butyl] dihydrogen phosphate
synonym: amiselimod-P
synonym: MT-1303-P
approved: f
ligand name: amiselimod phosphate
type: SyntheticOrganicLigand

telotristat ethyl
in ch i key: MDSQOJYHHZBZKA-GBXCKJPGSA-N
comment: Telotristat ethyl is an oral tryptophan hydroxylase inhibitor. Telotristat ethyl is the USAN, the INN is telotristat (represented in PubChem CID 25025298.
iupac name: ethyl (2S)-2-amino-3-[4-[2-amino-6-[(1R)-1-[4-chloro-2-(3-methylpyrazol-1-yl)phenyl]-2,2,2-trifluoroethoxy]pyrimidin-4-yl]phenyl]propanoate
xref: CHEMBL2105695
synonym: Xermelo®
synonym: LX1606
synonym: LX 1606
synonym: LX-1606
approved: t
ligand name: telotristat ethyl
type: SyntheticOrganicLigand

D-cycloserine
canonical SMILES: NC1CONC1=O
isomeric SMILES: N[C@@H]1CONC1=O
in ch i key: DYDCUQKUCUHJBH-UWTATZPHSA-N
in ch i: InChI=1S/C3H6N2O2/c4-2-1-7-5-3(2)6/h2H,1,4H2,(H,5,6)/t2-/m1/s1
comment: An analogue of the amino acid D-alanine and a component of the racemic drug with the INN cycloserine (D/<Ligand id=9488/>).
iupac name: (4R)-4-amino-1,2-oxazolidin-3-one
xref: CHEMBL771
synonym: Seromycin®
approved: t
ligand name: D-cycloserine
type: SyntheticOrganicLigand

L-cycloserine
canonical SMILES: NC1CONC1=O
isomeric SMILES: N[C@H]1CONC1=O
in ch i key: DYDCUQKUCUHJBH-REOHCLBHSA-N
in ch i: InChI=1S/C3H6N2O2/c4-2-1-7-5-3(2)6/h2H,1,4H2,(H,5,6)/t2-/m0/s1
comment: An analog of the amino acid D-alanine and a component of the racemic drug with the INN cycloserine (see also <Ligand id=9489/>).
iupac name: (4S)-4-amino-1,2-oxazolidin-3-one
xref: CHEMBL448864
synonym: levcycloserine
synonym: Seromycin®
approved: t
ligand name: L-cycloserine
type: SyntheticOrganicLigand

arecaidine
canonical SMILES: CN1CC(=CCC1)C(=O)O
isomeric SMILES: CN1CC(=CCC1)C(=O)O
in ch i key: DNJFTXKSFAMXQF-UHFFFAOYSA-N
in ch i: InChI=1S/C7H11NO2/c1-8-4-2-3-6(5-8)7(9)10/h3H,2,4-5H2,1H3,(H,9,10)
comment: Arecaidine is an alkaloid found in betel nuts (Areca catechu).
iupac name: 1-methyl-5,6-dihydro-2H-pyridine-3-carboxylic acid
xref: CHEMBL432561
synonym: methylguvacine
synonym: N-methylguvacine
approved: f
ligand name: arecaidine
type: SyntheticOrganicLigand

histidyl-leucine
canonical SMILES: NC(C(=O)NC(C(=O)O)CC(C)C)Cc1[nH]cnc1
in ch i key: MMFKFJORZBJVNF-UWVGGRQHSA-N
in ch i: InChI=1S/C12H20N4O3/c1-7(2)3-10(12(18)19)16-11(17)9(13)4-8-5-14-6-15-8/h5-7,9-10H,3-4,13H2,1-2H3,(H,14,15)(H,16,17)(H,18,19)/t9-,10-/m0/s1
iupac name: H-His-Leu-OH
xref: CHEMBL90260
synonym: L-histidyl-L-leucine
synonym: Histidylleucine
synonym: His-leu
approved: f
ligand name: histidyl-leucine
type: PeptideLigand

YM-244769
in ch i key: JZMLHJRKSJXARY-UHFFFAOYSA-N
in ch i: InChI=1S/C26H22FN3O3/c27-21-5-1-4-19(13-21)17-32-23-8-10-24(11-9-23)33-25-12-7-20(16-29-25)26(31)30-15-18-3-2-6-22(28)14-18/h1-14,16H,15,17,28H2,(H,30,31)
comment: YM-244769 is a novel potent Na+/Ca2+ exchange (NCX) inhibitor, with selectivity for NCX3 (SLC8A3) over the other SLC8 family exchangers <Reference id=32394/>.
iupac name: N-[(3-aminophenyl)methyl]-6-[4-[(3-fluorophenyl)methoxy]phenoxy]pyridine-3-carboxamide
synonym: YM244769
synonym: YM 244769
approved: f
ligand name: YM-244769
type: SyntheticOrganicLigand

GlcC14C18
in ch i key: HOINWSFARNFWIP-IGIMWDRYSA-N
in ch i: InChI=1S/C36H70O6/c1-3-5-7-9-11-13-15-16-18-20-22-24-26-28-31(27-25-23-21-19-17-14-12-10-8-6-4-2)35(39)41-30-34-32(37)29-33(38)36(40)42-34/h31-34,36-38,40H,3-30H2,1-2H3/t31?,32-,33?,34?,36+/m0/s1
comment: GlcC14C18 is one of the most potent vaccine adjuvants identified in <Reference id=32350/>.
iupac name: [(3S,6R)-3,5,6-trihydroxyoxan-2-yl]methyl 2-tridecylheptadecanoate
synonym: 6-O-(2'(R,S)-tetradecyloctadecanoyl)-D-glucose
approved: f
ligand name: GlcC14C18
type: SyntheticOrganicLigand

KML29
in ch i key: SXHQLPHDBLTFPM-UHFFFAOYSA-N
in ch i: InChI=1S/C24H21F6NO7/c25-23(26,27)20(24(28,29)30)38-21(32)31-7-5-13(6-8-31)22(33,14-1-3-16-18(9-14)36-11-34-16)15-2-4-17-19(10-15)37-12-35-17/h1-4,9-10,13,20,33H,5-8,11-12H2
comment: KML29 is a highly selective and potent monoacylglycerol lipase (MAGL) inhibitor. MAGL is the primary catabolic enzyme of the endogenous endocannabinoid 2-arachidonoylglycerol (2-AG). Selective MAGL inhibitors can be used as probes to investigate the consequences of elevating circulating levels of 2-AG levels in vivo.
iupac name: 1,1,1,3,3,3-hexafluoropropan-2-yl 4-[bis(1,3-benzodioxol-5-yl)-hydroxymethyl]piperidine-1-carboxylate
approved: f
ligand name: KML29
type: SyntheticOrganicLigand

JJKK 048
in ch i key: CLSNATLUIXZPMV-UHFFFAOYSA-N
in ch i: InChI=1S/C23H22N4O5/c28-23(27-12-24-11-25-27)26-7-5-15(6-8-26)22(16-1-3-18-20(9-16)31-13-29-18)17-2-4-19-21(10-17)32-14-30-19/h1-4,9-12,15,22H,5-8,13-14H2
comment: Potent and selective monoacylglycerol lipase (MAGL) inhibitor <Reference id=32363/><Reference id=32459/>.
iupac name: [4-[bis(1,3-benzodioxol-5-yl)methyl]piperidin-1-yl]-(1,2,4-triazol-1-yl)methanone
synonym: JJKK-048
approved: f
ligand name: JJKK 048
type: SyntheticOrganicLigand

WWL123
in ch i key: QKMMESWNJMOPIF-UHFFFAOYSA-N
in ch i: InChI=1S/C28H24N2O3/c1-30(19-20-7-5-10-24(17-20)21-8-3-2-4-9-21)28(32)33-26-12-6-11-25(18-26)22-13-15-23(16-14-22)27(29)31/h2-18H,19H2,1H3,(H2,29,31)
iupac name: [3-(4-carbamoylphenyl)phenyl] N-methyl-N-[(3-phenylphenyl)methyl]carbamate
approved: f
ligand name: WWL123
type: SyntheticOrganicLigand

adomeglivant
in ch i key: FASLTMSUPQDLIB-MHZLTWQESA-N
in ch i: InChI=1S/C32H36F3NO4/c1-20-18-26(19-21(2)29(20)23-10-12-25(13-11-23)31(3,4)5)40-27(14-16-32(33,34)35)22-6-8-24(9-7-22)30(39)36-17-15-28(37)38/h6-13,18-19,27H,14-17H2,1-5H3,(H,36,39)(H,37,38)/t27-/m0/s1
comment: Potent, selective small-molecule glucagon receptor antagonist that lowers glucose
iupac name: 3-[[4-[(1S)-1-[4-(4-tert-butylphenyl)-3,5-dimethylphenoxy]-4,4,4-trifluorobutyl]benzoyl]amino]propanoic acid
synonym: LY2409021
approved: t
ligand name: adomeglivant
type: SyntheticOrganicLigand

compound 8ic [PMID: 19081254]
in ch i key: WYVBISCFCHREDA-UHFFFAOYSA-N
in ch i: InChI=1S/C27H41N5O2/c1-33-24-18-22-23(19-25(24)34-2)29-27(30-26(22)28-20-10-6-3-4-7-11-20)32-16-12-21(13-17-32)31-14-8-5-9-15-31/h18-21H,3-17H2,1-2H3,(H,28,29,30)
comment: This Astellas Pharma compound 8ic is a potent competitive CCR4 antagonist. Oral administration showed anti-inflammatory activity in a murine model of acute dermatitis <Reference id=32342/> (n.b. caution, there is no specificity data in this paper). There are some data links for the dichloride (PubChem CID 56972238).
iupac name: N-cycloheptyl-6,7-dimethoxy-2-(4-piperidin-1-ylpiperidin-1-yl)quinazolin-4-amine
xref: CHEMBL508207
synonym: CCR4 Antagonist
approved: f
ligand name: compound 8ic [PMID: 19081254]
type: SyntheticOrganicLigand

deflazacort
in ch i key: FBHSPRKOSMHSIF-GRMWVWQJSA-N
in ch i: InChI=1S/C25H31NO6/c1-13-26-25(20(30)12-31-14(2)27)21(32-13)10-18-17-6-5-15-9-16(28)7-8-23(15,3)22(17)19(29)11-24(18,25)4/h7-9,17-19,21-22,29H,5-6,10-12H2,1-4H3/t17-,18-,19-,21+,22+,23-,24-,25+/m0/s1
comment: Deflazacort is a <Ligand id=2866/> derivative glucocorticoid that is used as an anti-inflammatory and immunosuppressant. It is a prodrug that is metabolised to the active form, 21-desacetyl deflazacort (PubChem CID 97547130) <Reference id=32435/>.
synonym: Emflaza®
synonym: MDL 458
synonym: MDL-458
synonym: MDL458
approved: t
ligand name: deflazacort
type: SyntheticOrganicLigand

SB-423562
in ch i key: NJBFJCJKWWIKRD-HSZRJFAPSA-N
in ch i: InChI=1S/C26H32N2O4/c1-26(2,14-19-11-20-5-3-4-6-21(20)12-19)28-16-23(29)17-32-24-13-18(8-10-25(30)31)7-9-22(24)15-27/h3-7,9,13,19,23,28-29H,8,10-12,14,16-17H2,1-2H3,(H,30,31)/t23-/m1/s1
comment: Calcium sensing receptor negative allosteric modulator
iupac name: 3-[4-cyano-3-[(2R)-3-[[1-(2,3-dihydro-1H-inden-2-yl)-2-methylpropan-2-yl]amino]-2-hydroxypropoxy]phenyl]propanoic acid
synonym: NPSP795
synonym: SHP-635
approved: f
ligand name: SB-423562
type: SyntheticOrganicLigand

ATF936
in ch i key: WXYYACUWOMKZQC-UHFFFAOYSA-N
in ch i: InChI=1S/C27H24N2O2/c1-4-16-31-23-14-15-25-24(17-23)26(22-12-10-21(11-13-22)19(2)3)28-27(30)29(25)18-20-8-6-5-7-9-20/h1,5-15,17,19H,16,18H2,2-3H3
comment: ATF936 is an orally bioavailable, negative allosteric modulator (NAM) of the calcium sensing receptor (CaSR) that was developed by Novartis <Reference id=32329/>. It acts to promote a rapid and transient release of parathyroid hormone which stimulates a calcilytic effect in vivo <Reference id=38890/>. CaSR antagonists/NAMs are being investigated as bone-forming osteoporosis therapeutics.
iupac name: 1-(phenylmethyl)-4-(4-propan-2-ylphenyl)-6-prop-2-ynoxyquinazolin-2-one
synonym: ATF-936
synonym: compound 10a [PMID: 20158186]
approved: f
ligand name: ATF936
type: SyntheticOrganicLigand

encaleret
in ch i key: UNFHDRVFEQPUEL-DENIHFKCSA-N
in ch i: InChI=1S/C29H33ClFNO4/c1-18-13-21(10-11-23(18)28(34)35)25-8-6-5-7-24(25)19(2)36-17-22(33)16-32-29(3,4)15-20-9-12-26(30)27(31)14-20/h5-14,19,22,32-33H,15-17H2,1-4H3,(H,34,35)/t19-,22-/m1/s1
comment: Calcium sensing receptor negative allosteric modulator
iupac name: 4-[2-[(1R)-1-[(2R)-3-[[1-(4-chloro-3-fluorophenyl)-2-methylpropan-2-yl]amino]-2-hydroxypropoxy]ethyl]phenyl]-2-methylbenzoic acid
synonym: JTT-305
synonym: MK5442
approved: f
ligand name: encaleret
type: SyntheticOrganicLigand

ronacaleret
in ch i key: FQJISUPNMFRIFZ-HXUWFJFHSA-N
in ch i: InChI=1S/C25H31F2NO4/c1-25(2,13-17-9-18-5-3-4-6-19(18)10-17)28-14-20(29)15-32-22-12-16(7-8-23(30)31)11-21(26)24(22)27/h3-6,11-12,17,20,28-29H,7-10,13-15H2,1-2H3,(H,30,31)/t20-/m1/s1
comment: Calcium sensing receptor negative allosteric modulator
iupac name: 3-[3-[(2R)-3-[[1-(2,3-dihydro-1H-inden-2-yl)-2-methylpropan-2-yl]amino]-2-hydroxypropoxy]-4,5-difluorophenyl]propanoic acid
synonym: SB-751689
approved: f
ligand name: ronacaleret
type: SyntheticOrganicLigand

MRS4183
in ch i key: DXQJLXWZLNCEJX-VBCGWZPHSA-N
comment: MRS4183 is a nanomolar affinity, fluorescent probe agonist of the P2Y14 receptor <Reference id=32315/>. The fluorophore is BODIPY (boron-dipyrromethene). A SMILES string was generated from the MOL file rendering of the structure provided with the article, as additional information <Reference id=32315/>.
synonym: compound 11 [PMID: 26303895]
approved: f
ligand name: MRS4183
type: SyntheticOrganicLigand

MRS4174
in ch i key: FMXSYRBHGUMFBA-UHFFFAOYSA-N
comment: MRS4174 is a very high affinity, fluorescent probe antagonist of the P2Y14 receptor <Reference id=32314/>. The flurophore is Alexa Fluor 488 (green fluorescence).
synonym: derivative 30 [PMID: 25299434]
approved: f
ligand name: MRS4174
type: SyntheticOrganicLigand

compound 12 [PMID: 27448772]
in ch i key: MJJJFOLDERHCND-UHFFFAOYSA-N
in ch i: InChI=1S/C22H25N5O4S/c1-13(2)31-18-14(22(30)27-9-7-26(3)8-10-27)5-4-6-16(18)25-20(28)15-11-32-19-17(15)23-12-24-21(19)29/h4-6,11-13H,7-10H2,1-3H3,(H,25,28)(H,23,24,29)
comment: Compound 12 [PMID: 27448772] is a potent and selective inhibitor of TAK1 (MAP3K7), developed in a structure based drug design programme <Reference id=32171/>, but the compound suffers from low permeability.
iupac name: N-[3-(4-methylpiperazine-1-carbonyl)-2-propan-2-yloxyphenyl]-4-oxo-1H-thieno[3,2-d]pyrimidine-7-carboxamide
approved: f
ligand name: compound 12 [PMID: 27448772]
type: SyntheticOrganicLigand

PKCθ inhibitor 14
in ch i key: WNYKGJHEQVIFGL-OAHLLOKOSA-N
in ch i: InChI=1S/C24H23N5O2/c1-15(16-8-5-4-6-9-16)29-20-14-17(11-12-18(20)22(30)27-24(29,2)3)28-19-10-7-13-25-21(19)26-23(28)31/h4-15H,1-3H3,(H,27,30)(H,25,26,31)/t15-/m1/s1
comment: PKCθ inhibitor 14 was developed using structure-based drug design <Reference id=32163/>. The compound is described as being selective for PKCθ, over other kinases, including related PKC isoforms.
iupac name: 2,2-dimethyl-7-(2-oxo-3H-imidazo[4,5-b]pyridin-1-yl)-1-[(1R)-1-phenylethyl]-3H-quinazolin-4-one
synonym: compound 14 [PMID: 27117263]
approved: f
ligand name: PKCθ inhibitor 14
type: SyntheticOrganicLigand

MRS4162
in ch i key: IKFGJXBDIZQEHP-NJFIWEGUSA-N
comment: MRS4162 is a BODIPY 630/650 conjugated P2Y6 receptor agonist that is useful as a molecular probe <Reference id=32300/>. Although it exhibits activity at the P2Y2 and P2Y4 receptors in intracellular signalling assays, it selectively labels P2Y6 receptors in cellular assays.
xref: CHEMBL3261378
synonym: BODIPY 630/650 conjugate 28
approved: f
ligand name: MRS4162
type: SyntheticOrganicLigand

PSB-416
in ch i key: MURCBJRRFKMCAT-UHFFFAOYSA-N
in ch i: InChI=1S/C21H16N2O6S/c1-29-12-8-6-11(7-9-12)23-15-10-16(30(26,27)28)19(22)18-17(15)20(24)13-4-2-3-5-14(13)21(18)25/h2-10,23H,22H2,1H3,(H,26,27,28)
comment: PSB-416 (compound 8) is an anthraquinone derivative showing antagonistic effects at the P2Y2 receptor <Reference id=32299/>.
iupac name: 1-amino-4-(4-methoxyanilino)-9,10-dioxoanthracene-2-sulfonic acid
xref: CHEMBL1207381
synonym: SB-416
approved: f
ligand name: PSB-416
type: SyntheticOrganicLigand

[3H]EMPA
in ch i key: KJPHTXTWFHVJIG-MJVMYBOOSA-N
in ch i: InChI=1S/C23H26N4O4S/c1-4-26(16-19-9-7-13-24-14-19)23(28)17-27(20-11-12-22(31-3)25-15-20)32(29,30)21-10-6-5-8-18(21)2/h5-15H,4,16-17H2,1-3H3/i3T3,13T
comment: A radiolabelled version of the OX2 receptor-selective antagonist <Ligand id=4037/> <Reference id=15233/>.
xref: CHEMBL2385133
approved: f
ligand name: [3H]EMPA
type: SyntheticOrganicLigand

LUF6096
in ch i key: UWEIQVQNNLVOEI-UHFFFAOYSA-N
in ch i: InChI=1S/C22H21Cl2N3O/c23-17-11-10-15(12-18(17)24)25-21-13-20(16-8-4-5-9-19(16)26-21)27-22(28)14-6-2-1-3-7-14/h4-5,8-14H,1-3,6-7H2,(H2,25,26,27,28)
comment: Positive allosteric modulator of the human A3 adenosine receptor.
iupac name: N-[2-(3,4-dichloroanilino)quinolin-4-yl]cyclohexanecarboxamide
approved: f
ligand name: LUF6096
type: SyntheticOrganicLigand

[3H]Cp-1
in ch i key: FIINKDGVMNTVCW-UCOREUHWSA-N
in ch i: InChI=1S/C28H30F3N3O3/c1-32-27(35)26(19-7-5-4-6-8-19)34-14-13-20-15-23(36-2)24(37-3)16-21(20)22(34)11-9-18-10-12-25(33-17-18)28(29,30)31/h4-8,10,12,15-17,22,26H,9,11,13-14H2,1-3H3,(H,32,35)/t22-,26+/m0/s1/i7T,17T
comment: [3H]Cp-1 is a radiolabelled <Ligand id=2886/> analogue. Structure provided in <Reference id=16455/>. It is a weakly OX2-selective antagonist.
approved: f
ligand name: [3H]Cp-1
type: SyntheticOrganicLigand

[3H]-almorexant
in ch i key: DKMACHNQISHMDN-AJYYXEBVSA-N
in ch i: InChI=1S/C29H31F3N2O3/c1-33-28(35)27(20-7-5-4-6-8-20)34-16-15-21-17-25(36-2)26(37-3)18-23(21)24(34)14-11-19-9-12-22(13-10-19)29(30,31)32/h4-10,12-13,17-18,24,27H,11,14-16H2,1-3H3,(H,33,35)/t24-,27+/m0/s1/i7T,8T
comment: A tritiated version of the orexin antagonist <Ligand id=2886/>; weakly OX2-selective. Position of tritium ions taken from <Reference id=16455/>.
approved: f
ligand name: [3H]-almorexant
type: SyntheticOrganicLigand

navamepent
canonical SMILES: C#CCC(C=CC=CC#CC(CCCC(=O)OC(C)C)O)O
isomeric SMILES: C#CC[C@H](/C=C/C=C/C#C[C@H](CCCC(=O)OC(C)C)O)O
in ch i key: ZVOCIIHCJJEFRQ-BHXBHYJPSA-N
in ch i: InChI=1S/C18H24O4/c1-4-10-16(19)11-7-5-6-8-12-17(20)13-9-14-18(21)22-15(2)3/h1,5-7,11,15-17,19-20H,9-10,13-14H2,2-3H3/b6-5+,11-7+/t16-,17-/m1/s1
comment: Navamepent (RX-10045) is a stable <Ligand id=3333/> analogue, that is being investigated for clinical efficacy in occular inflammation <Reference id=35314/>. Chemically this is an isopropyl ester prodrug of resolvin E1 (an agonist of the chemerin receptor). The chemical structure is claimed in patent US20140275247A1 (as Example 1001) <Reference id=35317/>. Findings from animal studies are reported in <Reference id=32258/> and <Reference id=32259/>.
iupac name: propan-2-yl (5S,8E,10E,12R)-5,12-dihydroxypentadeca-8,10-dien-6,14-diynoate
synonym: RX-10045
approved: f
ligand name: navamepent
type: SyntheticOrganicLigand

LY2940094
in ch i key: NKQHBJNRBKHUQR-UHFFFAOYSA-N
comment: LY2940094 is a potent and selective nociceptin receptor antagonist <Reference id=32251/>, with potential clinical utility as a treatment for neurobehavioral disorders <Reference id=41553/><Reference id=32254/>.
iupac name: [2-[4-[(2-chloro-4,4-difluorospiro[5H-thieno[2,3-c]pyran-7,4'-piperidine]-1'-yl)methyl]-3-methylpyrazol-1-yl]pyridin-3-yl]methanol
xref: CHEMBL3304244
synonym: compound 36 [PMID: 24678969]
synonym: LY-2940094
synonym: BTRX-246040
approved: f
ligand name: LY2940094
type: SyntheticOrganicLigand

L-732,138
in ch i key: BYYQYXVAWXAYQC-IBGZPJMESA-N
in ch i: InChI=1S/C22H18F6N2O3/c1-12(31)30-19(8-14-10-29-18-5-3-2-4-17(14)18)20(32)33-11-13-6-15(21(23,24)25)9-16(7-13)22(26,27)28/h2-7,9-10,19,29H,8,11H2,1H3,(H,30,31)/t19-/m0/s1
comment: L-732,138 is a competitive and selective NK1 receptor antagonist <Reference id=32246/>.
iupac name: [3,5-bis(trifluoromethyl)phenyl]methyl (2S)-2-acetamido-3-(1H-indol-3-yl)propanoate
xref: CHEMBL22870
synonym: L-732138
synonym: L732138
approved: f
ligand name: L-732,138
type: SyntheticOrganicLigand

AC264613
isomeric SMILES: Brc1cccc(c1)/C(=N/NC(=O)[C@@H]1C(=O)NC[C@H]1c1ccccc1)/C
in ch i key: RQKXQCSEZPQBNZ-QSBCOWLBSA-N
in ch i: InChI=1S/C19H18BrN3O2/c1-12(14-8-5-9-15(20)10-14)22-23-19(25)17-16(11-21-18(17)24)13-6-3-2-4-7-13/h2-10,16-17H,11H2,1H3,(H,21,24)(H,23,25)/b22-12+/t16-,17-/m0/s1
comment: AC264613 is a potent and selective, small molecule agonist of the PAR2 receptor <Reference id=32239/>. It is a suitable pharmacological tool for examining the functions of PAR2 receptors.
iupac name: (3S,4R)-N-[(E)-1-(3-bromophenyl)ethylideneamino]-2-oxo-4-phenylpyrrolidine-3-carboxamide
xref: CHEMBL494502
synonym: AC-264613
synonym: compound 3 [PMID: 18720984]
approved: f
ligand name: AC264613
type: SyntheticOrganicLigand

ML354
canonical SMILES: OCc1c(c2ccccc2)c2c(n1C)ccc(c2)[N+](=O)[O-]
isomeric SMILES: OCc1c(c2ccccc2)c2c(n1C)ccc(c2)[N+](=O)[O-]
in ch i key: GNJUKVGDCUKDLF-UHFFFAOYSA-N
in ch i: InChI=1S/C16H14N2O3/c1-17-14-8-7-12(18(20)21)9-13(14)16(15(17)10-19)11-5-3-2-4-6-11/h2-9,19H,10H2,1H3
comment: ML354 is a PAR4 receptor antagonist <Reference id=32242/>.
iupac name: (1-methyl-5-nitro-3-phenylindol-2-yl)methanol
xref: CHEMBL1609104
synonym: VU0099704
approved: f
ligand name: ML354
type: SyntheticOrganicLigand

dexmethylphenidate
canonical SMILES: COC(=O)C(c1ccccc1)C1CCCCN1
isomeric SMILES: COC(=O)[C@H](c1ccccc1)[C@H]1CCCCN1
in ch i key: DUGOZIWVEXMGBE-CHWSQXEVSA-N
in ch i: InChI=1S/C14H19NO2/c1-17-14(16)13(11-7-3-2-4-8-11)12-9-5-6-10-15-12/h2-4,7-8,12-13,15H,5-6,9-10H2,1H3/t12-,13-/m1/s1
comment: Dexmethylphenidate is a phenethylamine and piperidine class central nervous system stimulant. Chemically, it is the active dextrorotatory (R,R) enantiomer of racemic <Ligand id=7236/>.
iupac name: methyl (2R)-2-phenyl-2-[(2R)-piperidin-2-yl]acetate
xref: CHEMBL827
synonym: D-TMP
synonym: Attenade®
synonym: Focalin®
approved: t
ligand name: dexmethylphenidate
type: SyntheticOrganicLigand

YD-3
in ch i key: LPROLPQTWKDPNU-UHFFFAOYSA-N
in ch i: InChI=1S/C23H20N2O2/c1-2-27-23(26)19-14-12-18(13-15-19)22-20-10-6-7-11-21(20)25(24-22)16-17-8-4-3-5-9-17/h3-15H,2,16H2,1H3
comment: YD-3 is a selective PAR4 antagonist <Reference id=32240/>.
xref: CHEMBL125021
approved: f
ligand name: YD-3
type: SyntheticOrganicLigand

AC-98170
canonical SMILES: O=C(C1C(=O)NCC1c1ccccc1)NN=C(c1cccs1)C
isomeric SMILES: O=C([C@@H]1C(=O)NC[C@H]1c1ccccc1)N/N=C(/c1cccs1)/C
in ch i key: GNFXCDMTRHENBV-CJINARDKSA-N
in ch i: InChI=1S/C17H17N3O2S/c1-11(14-8-5-9-23-14)19-20-17(22)15-13(10-18-16(15)21)12-6-3-2-4-7-12/h2-9,13,15H,10H2,1H3,(H,18,21)(H,20,22)/b19-11+/t13-,15-/m0/s1
comment: AC-98170 is a potent and selective small-molecule PAR2 agonist <Reference id=32239/>. The compound is a metabolically stable pharmacological tool for studying PAR2 receptors.
iupac name: (3S,4R)-2-oxo-4-phenyl-N-[(E)-1-thiophen-2-ylethylideneamino]pyrrolidine-3-carboxamide
xref: CHEMBL494303
synonym: AC98170
approved: f
ligand name: AC-98170
type: SyntheticOrganicLigand

AC-55541
in ch i key: UCUHFWIFSHROPY-RWPZCVJISA-N
in ch i: InChI=1S/C25H20BrN5O3/c1-15(17-10-7-11-18(26)14-17)28-31-25(34)22(27-23(32)16-8-3-2-4-9-16)21-19-12-5-6-13-20(19)24(33)30-29-21/h2-14,22H,1H3,(H,27,32)(H,30,33)(H,31,34)/b28-15+
comment: AC-55541 is a potent and selective small-molecule PAR2 agonist <Reference id=32239/>. The compound is a metabolically stable pharmacological tool for studying PAR2 receptors.
iupac name: N-[2-[(2E)-2-[1-(3-bromophenyl)ethylidene]hydrazinyl]-2-oxo-1-(4-oxo-3H-phthalazin-1-yl)ethyl]benzamide
xref: CHEMBL493076
synonym: AC55541
approved: f
ligand name: AC-55541
type: SyntheticOrganicLigand

PQA-18
in ch i key: APPXFGJVXDYNBO-UHFFFAOYSA-N
in ch i: InChI=1S/C25H31NO4/c1-17(2)10-13-28-22-9-7-8-20-23(29-14-11-18(3)4)16-21(26-24(20)22)25(27)30-15-12-19(5)6/h7-12,16H,13-15H2,1-6H3
comment: PQA-18 is a novel, non-competitive PAK2 inhibitor with potent immunosuppresive activity <Reference id=32194/>. It is a derivative of the natural metabolite Ppc-1 (PubChem CID 46910769) extracted from Polysphondylium pseudo-candidum.
iupac name: 3-methylbut-2-enyl 4-methoxy-8-(3-methylbut-2-enoxy)quinoline-2-carboxylate
xref: CHEMBL3355920
approved: f
ligand name: PQA-18
type: SyntheticOrganicLigand

DF2593A
in ch i key: QCZKLPFIGVYGPA-CQSZACIVSA-N
comment: Selective C5a receptor noncompetitive allosteric inhibitor.
iupac name: [4-[(1R)-1-(4-piperidin-1-ylbutanoylamino)ethyl]phenyl] trifluoromethanesulfonate
approved: f
ligand name: DF2593A
type: SyntheticOrganicLigand

avacopan
in ch i key: PUKBOVABABRILL-YZNIXAGQSA-N
in ch i: InChI=1S/C33H35F4N3O2/c1-20-12-15-25(19-27(20)33(35,36)37)39-31(41)26-10-6-18-40(32(42)29-21(2)7-5-11-28(29)34)30(26)22-13-16-24(17-14-22)38-23-8-3-4-9-23/h5,7,11-17,19,23,26,30,38H,3-4,6,8-10,18H2,1-2H3,(H,39,41)/t26-,30-/m0/s1
comment: Avacopan is a small molecule, competitive and orally bioactive antagonist of human C5a1 receptor <Reference id=32151/>. It was originally proposed as an alternative to steroid (glucocorticoid) therapy for ANCA-associated vasculitis <Reference id=43042/><Reference id=41073/>. The evidence confirming C5, C5a and the C5a receptor as anti-inflammatory and anti-cancer drug targets was reviewed by Horiuchi and Tsukamoto (2016) <Reference id=34089/>.
iupac name: (2R,3S)-2-[4-(cyclopentylamino)phenyl]-1-(2-fluoro-6-methylbenzoyl)-N-[4-methyl-3-(trifluoromethyl)phenyl]piperidine-3-carboxamide
synonym: CCX-168
synonym: CCX168
synonym: Tavneos®
approved: t
ligand name: avacopan
type: SyntheticOrganicLigand

compound 17 [PMID: 24257095]
in ch i key: WGEOKEOSKNNXJR-ROUUACIJSA-N
in ch i: InChI=1S/C24H31N7O5/c1-13(2)10-18(30-20(32)15-11-28-16-7-4-3-6-14(15)16)22-31-19(12-36-22)21(33)29-17(23(34)35)8-5-9-27-24(25)26/h3-4,6-7,11-13,17-18,28H,5,8-10H2,1-2H3,(H,29,33)(H,30,32)(H,34,35)(H4,25,26,27)/t17-,18-/m0/s1
comment: Potent small molecule agonist of the C3a receptor.
iupac name: (2S)-5-(diaminomethylideneamino)-2-[[2-[(1S)-1-(1H-indole-3-carbonylamino)-3-methylbutyl]-1,3-oxazole-4-carbonyl]amino]pentanoic acid
approved: f
ligand name: compound 17 [PMID: 24257095]
type: SyntheticOrganicLigand

CMF-019
in ch i key: VCQKKZXFASLXAH-SFHVURJKSA-N
in ch i: InChI=1S/C25H33N3O3S/c1-5-19(6-2)28-22-10-9-17(25(31)26-18(12-16(3)4)14-24(29)30)13-21(22)27-23(28)15-20-8-7-11-32-20/h7-11,13,16,18-19H,5-6,12,14-15H2,1-4H3,(H,26,31)(H,29,30)/t18-/m0/s1
comment: Biased small molecule agonist at the apelin receptor. For in vivo studies the potassium salt of the compound was used <Reference id=32127/>.
iupac name: (3S)-5-methyl-3-[[1-pentan-3-yl-2-(thiophen-2-ylmethyl)benzimidazole-5-carbonyl]amino]hexanoic acid
approved: f
ligand name: CMF-019
type: SyntheticOrganicLigand

LUF6000
in ch i key: UWJVRSIGHHSDSJ-UHFFFAOYSA-N
in ch i: InChI=1S/C22H20Cl2N4/c23-16-11-10-14(12-17(16)24)25-22-20-19(15-8-4-5-9-18(15)26-22)27-21(28-20)13-6-2-1-3-7-13/h4-5,8-13H,1-3,6-7H2,(H,25,26)(H,27,28)
comment: Positive allosteric modulator of the human A3 adenosine receptor.
iupac name: 2-cyclohexyl-N-(3,4-dichlorophenyl)-3H-imidazo[5,4-c]quinolin-4-amine
approved: f
ligand name: LUF6000
type: SyntheticOrganicLigand

PD81723
canonical SMILES: Nc1sc(c(c1C(=O)c1cccc(c1)C(F)(F)F)C)C
isomeric SMILES: Nc1sc(c(c1C(=O)c1cccc(c1)C(F)(F)F)C)C
in ch i key: KKDKAWKYGCUOGR-UHFFFAOYSA-N
in ch i: InChI=1S/C14H12F3NOS/c1-7-8(2)20-13(18)11(7)12(19)9-4-3-5-10(6-9)14(15,16)17/h3-6H,18H2,1-2H3
comment: Allosteric potentiator at the adenosine A1 receptor.
iupac name: (2-amino-4,5-dimethylthiophen-3-yl)-[3-(trifluoromethyl)phenyl]methanone
approved: f
ligand name: PD81723
type: SyntheticOrganicLigand

intepirdine
in ch i key: JJZFWROHYSMCMU-UHFFFAOYSA-N
in ch i: InChI=1S/C19H19N3O2S/c23-25(24,16-6-2-1-3-7-16)17-13-15-5-4-8-18(19(15)21-14-17)22-11-9-20-10-12-22/h1-8,13-14,20H,9-12H2
comment: Intepirdine (RVT-101) is a 5-HT6 receptor antagonist <Reference id=32115/> (called SB-742457 in this article). Developed by Axovant Science Ltd. Phase 3 clinical trial results for RVT-101 are eagerly awaited given the reported failures of competitors' 5-HT6 receptor antagonists in Alzheimer's disease trials (e.g. Lundbeck's <Ligand id=8689/>, and Pfizer's PF-05212377).
iupac name: 3-(benzenesulfonyl)-8-piperazin-1-ylquinoline
xref: CHEMBL1083390
synonym: RVT-101
synonym: SB-742457
synonym: GSK742457
approved: f
ligand name: intepirdine
type: SyntheticOrganicLigand

compound 25e [PMID: 25875054]
in ch i key: BSGIKRCNMBTGEB-UHFFFAOYSA-N
in ch i: InChI=1S/C22H25BrN4O/c1-14-11-27(13-16-6-5-15(7-18(14)16)12-25(2)3)22(28)19-8-17-9-21(23)24-10-20(17)26(19)4/h5-10,14H,11-13H2,1-4H3
comment: For the original publication reporting the design and development of the series of pyrrolo[2,3-c]pyridines as QRFP receptor small molecule antagonists, including compound 25e, see <Reference id=32112/>.
iupac name: (5-Bromo-1-methyl-1H-pyrrolo[2,3-c]pyridin-2-yl){6-[(dimethylamino)methyl]-(+)-4-methyl-3,4-dihydroisoquinolin-2(1H)-yl}methanone
xref: CHEMBL3314358
synonym: (5-Bromo-1-methyl-1H-pyrrolo[2,3-c]pyridin-2-yl){6-[(dimethylamino)methyl]-(+)-4-methyl-3,4-dihydroisoquinolin-2(1H)-yl}methanone
approved: f
ligand name: compound 25e [PMID: 25875054]
type: SyntheticOrganicLigand

[Orn5]URP
in ch i key: AJUZRHILBXDUEG-LSKWFVNGSA-N
approved: f
ligand name: [Orn5]URP
type: PeptideLigand

JNJ-39319202
in ch i key: MWCLCGKVMLYVJI-RUZDIDTESA-N
in ch i: InChI=1S/C30H38N4O5S2/c1-4-32-15-17-33(18-16-32)26-9-5-8-23-24(26)21-34(30(23)35)25(22-12-13-27(38-2)28(20-22)39-3)10-6-14-31-41(36,37)29-11-7-19-40-29/h5,7-9,11-13,19-20,25,31H,4,6,10,14-18,21H2,1-3H3/t25-/m1/s1
iupac name: N-[(4R)-4-(3,4-dimethoxyphenyl)-4-[7-(4-ethylpiperazin-1-yl)-3-oxo-1H-isoindol-2-yl]butyl]thiophene-2-sulfonamide
synonym: compound 7a [PMID: 19731961]
approved: f
ligand name: JNJ-39319202
type: SyntheticOrganicLigand

PF-06263276
in ch i key: XDJGNPSZQSWJCV-UHFFFAOYSA-N
in ch i: InChI=1S/C31H31FN8O2/c1-2-18-13-27(41)22(32)14-21(18)19-6-7-20-24(12-19)37-38-29(20)30-35-23-8-11-40(17-26(23)36-30)31(42)25-15-34-28(16-33-25)39-9-4-3-5-10-39/h6-7,12-16,41H,2-5,8-11,17H2,1H3,(H,35,36)(H,37,38)
comment: PF-06263276 is a pan-JAK inhibitor <Reference id=31980/>. There are two E/Z isomers as PubChem CID 122196621 and PubChem CID 71495793 but these are not resolved in the publication.
iupac name: 2-[6-(2-Ethyl-5- fl uoro-4-hydroxyphenyl)-1 H -indazol-3-yl]- 1,4,6,7-tetrahydroimidazo[4,5- c ]pyridin-5-yl-(5-piperidin-1-yl- pyrazin-2-yl)methanone
synonym: compound 2 [PMID: 27983835]
synonym: PF 0626327
synonym: PF0626327
approved: f
ligand name: PF-06263276
type: SyntheticOrganicLigand

CCR2-RA-[R]
in ch i key: VQNLJXWZGVRLBA-MRXNPFEDSA-N
in ch i: InChI=1S/C18H19ClFNO3/c1-10(22)15-16(11-5-3-2-4-6-11)21(18(24)17(15)23)14-8-7-12(19)9-13(14)20/h7-9,11,16,23H,2-6H2,1H3/t16-/m1/s1
comment: CCR2-RA-[R] is an allosteric antagonist of the CC chemokine receptor 2 (CCR2) <Reference id=31974/>. Allosteric modulation by CCR2-RA-[R] prevents formation of the G-protein-binding interface and hence G-protein coupling by blocking the required activation-associated changes in receptor conformation <Reference id=31975/>. The chemical structure presented here is that held with the PDB X-ray structure reported in <Reference id=31975/>. CCR2-RA-[R] is claimed as chiral example 125 in patent US6936633 <Reference id=31976/>.
iupac name: (2R)-3-acetyl-1-(4-chloro-2-fluorophenyl)-2-cyclohexyl-4-hydroxy-2H-pyrrol-5-one
synonym: analog 49 (Dasse et al., 2007)
approved: f
ligand name: CCR2-RA-[R]
type: SyntheticOrganicLigand

BMS-681
in ch i key: NUJWKQSEJDYCDB-GNRVTEMESA-N
in ch i: InChI=1S/C26H36F3N5O/c1-5-6-17-13-19(33(4)16(2)3)8-10-23(17)34-12-11-22(25(34)35)32-24-20-14-18(26(27,28)29)7-9-21(20)30-15-31-24/h7,9,14-17,19,22-23H,5-6,8,10-13H2,1-4H3,(H,30,31,32)/t17-,19-,22+,23+/m1/s1
comment: BMS-681 is an orthosteric antagonist of CC chemokine receptors 2 and 5 (CCR2 and CCR5) <Reference id=31972/>.
iupac name: (3S)-1-[(1S,2R,4R)-4-[methyl(propan-2-yl)amino]-2-propylcyclohexyl]-3-{[6-(trifluoromethyl)quinazolin-4-yl]amino}pyrrolidin-2-one
xref: CHEMBL3577945
synonym: compound 13d [PMID: 25893046]
approved: f
ligand name: BMS-681
type: SyntheticOrganicLigand

miransertib
in ch i key: HNFMVVHMKGFCMB-UHFFFAOYSA-N
in ch i: InChI=1S/C27H24N6/c28-24-21(8-4-17-30-24)25-32-23-14-13-22(18-6-2-1-3-7-18)31-26(23)33(25)20-11-9-19(10-12-20)27(29)15-5-16-27/h1-4,6-14,17H,5,15-16,29H2,(H2,28,30)
comment: Miransertib (ARQ-092) is an orally active, selective, and potent allosteric AKT inhibitor <Reference id=31961/>, being developed for antineoplastic potential.
iupac name: 3-[3-[4-(1-aminocyclobutyl)phenyl]-5-phenylimidazo[4,5-b]pyridin-2-yl]pyridin-2-amine
synonym: ARQ-092
synonym: ARQ 092
synonym: compound 21a [PMID: 27305487]
approved: f
ligand name: miransertib
type: SyntheticOrganicLigand

fruquintinib
in ch i key: BALLNEJQLSTPIO-UHFFFAOYSA-N
in ch i: InChI=1S/C21H19N3O5/c1-11-19(20(25)22-2)13-6-5-12(7-16(13)28-11)29-21-14-8-17(26-3)18(27-4)9-15(14)23-10-24-21/h5-10H,1-4H3,(H,22,25)
comment: Fruquintinib (HMPL-013) is a potent and selective inhibitor of VEGFR 1, 2, 3 tyrosine kinases, being developed for potential antineoplastic efficacy <Reference id=31960/>; preclinical data is reported in this reference.
iupac name: 6-(6,7-dimethoxyquinazolin-4-yl)oxy-N,2-dimethyl-1-benzofuran-3-carboxamide
synonym: HMPL-013
synonym: Elunate®
synonym: HMPL013
approved: t
ligand name: fruquintinib
type: SyntheticOrganicLigand

empesertib
in ch i key: NRJKIOCCERLIDG-GOSISDBHSA-N
in ch i: InChI=1S/C29H26FN5O4S/c1-18(19-4-9-22(30)10-5-19)28(36)31-23-11-6-20(7-12-23)21-8-15-27-33-29(34-35(27)17-21)32-25-14-13-24(40(3,37)38)16-26(25)39-2/h4-18H,1-3H3,(H,31,36)(H,32,34)/t18-/m1/s1
comment: Empesertib (BAY1161909) is an orally bioavailable, selective inhibitor of the monopolar spindle 1 (Mps1; gene symbol TTK) serine/threonine kinase <Reference id=31959/>.
iupac name: (2R)-2-(4-fluorophenyl)-N-[4-[2-(2-methoxy-4-methylsulfonylanilino)-[1,2,4]triazolo[1,5-a]pyridin-6-yl]phenyl]propanamide
synonym: BAY1161909
synonym: BAY-1161909
synonym: Mps1-IN-5
approved: f
ligand name: empesertib
type: SyntheticOrganicLigand

citarinostat
in ch i key: VLIUIBXPEDFJRF-UHFFFAOYSA-N
in ch i: InChI=1S/C24H26ClN5O3/c25-20-12-7-8-13-21(20)30(19-10-4-3-5-11-19)24-27-16-18(17-28-24)23(32)26-15-9-2-1-6-14-22(31)29-33/h3-5,7-8,10-13,16-17,33H,1-2,6,9,14-15H2,(H,26,32)(H,29,31)
comment: Citarinostat (ACY-241) is a next-generation HDAC6 inhibitor, that is under investigation for potential antineoplastic activity <Reference id=31958/>. Note that it exhibits only ~10-fold enzymic selectivity against the class I isoform, HDAC1.
iupac name: 2-(N-(2-chlorophenyl)anilino)-N-[7-(hydroxyamino)-7-oxoheptyl]pyrimidine-5-carboxamide
xref: CHEMBL3693786
synonym: HDAC-IN-2
synonym: Compound (I) [WO2016200919]
synonym: ACY-241
approved: f
ligand name: citarinostat
type: SyntheticOrganicLigand

nemiralisib
in ch i key: MCIDWGZGWVSZMK-UHFFFAOYSA-N
in ch i: InChI=1S/C26H28N6O/c1-17(2)32-10-8-31(9-11-32)16-19-14-28-26(33-19)22-12-18(13-25-23(22)15-29-30-25)20-4-3-5-24-21(20)6-7-27-24/h3-7,12-15,17,27H,8-11,16H2,1-2H3,(H,29,30)
comment: Nemiralisib (GSK2269557) is a PI3K inhibitor with selectivity for PI3Kδ over the other related isoforms <Reference id=31956/>. The compound is active via inhalation and is being evaluated for its potential in respiratory inflammation. May be administered or used experimentally as the hydrochloride salt (PubChem CID 49784084). In the original study by Down et al. (2015) compound 3 (<Ligand id=10633/>) was developed as a follow-up compound with reduced hERG activity and minimised systemic exposure <Reference id=31956/>.
iupac name: 2-[6-(1H-indol-4-yl)-1H-indazol-4-yl]-5-[(4-propan-2-ylpiperazin-1-yl)methyl]-1,3-oxazole
xref: CHEMBL2216859
synonym: GSK2269557
synonym: GSK-2269557
synonym: compound 2 [PMID: 26301626]
approved: f
ligand name: nemiralisib
type: SyntheticOrganicLigand

leniolisib
in ch i key: MWKYMZXCGYXLPL-ZDUSSCGKSA-N
in ch i: InChI=1S/C21H25F3N6O2/c1-3-18(31)30-6-4-13(10-30)28-19-15-11-29(7-5-17(15)26-12-27-19)14-8-16(21(22,23)24)20(32-2)25-9-14/h8-9,12-13H,3-7,10-11H2,1-2H3,(H,26,27,28)/t13-/m0/s1
comment: Leniolisib is an orally active, potent phosphatidylinositol 3-kinase inhibitor (PI3K) inhibitor, with selectivity for the PI3Kδ isoform <Reference id=33664/>. Novartis originally developed CDZ173 as a treatment for autoimmune diseases, but has rapidly repurposed it for its potential in patients with Activated PI3K Delta Syndrome (APDS, a.k.a. p110 delta activating mutation causing senescent T cells, lymphadenopathy and immunodeficiency, or PASLI). APDS is a rare genetic immunodeficiency disease characterised by lymphoproliferation, recurrent infections from childhood, and an increased risk of EBV-associated lymphoma. APDS is known to be caused by autosomal dominant, gain-of-function mutations in the PIK3CD gene which encodes the PI3Kδ protein <Reference id=31949/><Reference id=31950/>.
iupac name: 1-[(3S)-3-[[6-[6-methoxy-5-(trifluoromethyl)pyridin-3-yl]-7,8-dihydro-5H-pyrido[4,3-d]pyrimidin-4-yl]amino]pyrrolidin-1-yl]propan-1-one
xref: CHEMBL3643413
synonym: CDZ173
synonym: CDZ-173
synonym: CDZ 173
synonym: Example 67 [WO2012004299]
approved: f
ligand name: leniolisib
type: SyntheticOrganicLigand

compound 14n [PMID: 25589934]
in ch i key: DDKHTWASHUKHLD-UHFFFAOYSA-N
comment: Compound 14n is an inhibitor of serum/glucocorticoid regulated kinases, with moderate selectivity for SGK1 and SGK2 over SGK3<Reference id=31948/>.
iupac name: N-[4-(3-amino-2H-pyrazolo[3,4-b]pyrazin-6-yl)phenyl]-5-chloro-2-fluorobenzenesulfonamide
xref: CHEMBL3092468
approved: f
ligand name: compound 14n [PMID: 25589934]
type: SyntheticOrganicLigand

DAPK inhibitor 13
canonical SMILES: O=C1OC(=NC1=Cc1cccnc1)c1ccc(c(c1)C)Br
isomeric SMILES: O=C1OC(=N/C/1=C/c1cccnc1)c1ccc(c(c1)C)Br
in ch i key: AIDLMCGWDDGYCV-RIYZIHGNSA-N
in ch i: InChI=1S/C16H11BrN2O2/c1-10-7-12(4-5-13(10)17)15-19-14(16(20)21-15)8-11-3-2-6-18-9-11/h2-9H,1H3/b14-8+
comment: DAPK inhibitor 13 is a pan DAPK inhibitor <Reference id=31947/><Reference id=31946/>.
iupac name: (4E)-2-(4-bromo-3-methylphenyl)-4-(pyridin-3-ylmethylidene)-1,3-oxazol-5-one
synonym: i-13
synonym: compound 13 [PMID: 20206532]
approved: f
ligand name: DAPK inhibitor 13
type: SyntheticOrganicLigand

esflurbiprofen
canonical SMILES: OC(=O)C(c1ccc(c(c1)F)c1ccccc1)C
isomeric SMILES: OC(=O)[C@H](c1ccc(c(c1)F)c1ccccc1)C
in ch i key: SYTBZMRGLBWNTM-JTQLQIEISA-N
in ch i: InChI=1S/C15H13FO2/c1-10(15(17)18)12-7-8-13(14(16)9-12)11-5-3-2-4-6-11/h2-10H,1H3,(H,17,18)/t10-/m0/s1
comment: Esflurbiprofen is a topically applied, non-steroidal anti inflammatory drug (NSAID). It is the more active enantiomer of racemic <Ligand id=4194/>.
iupac name: (2S)-2-(3-fluoro-4-phenylphenyl)propanoic acid
xref: CHEMBL435298
synonym: SFPP
synonym: BTS-24332
synonym: TT-063
synonym: (S)-flurbiprofen
approved: t
ligand name: esflurbiprofen
type: SyntheticOrganicLigand

Nexinhib20
canonical SMILES: O=C(C(C)(C)C)C(=Cc1cccc(c1)[N+](=O)[O-])n1cncn1
isomeric SMILES: O=C(C(C)(C)C)/C(=C/c1cccc(c1)[N+](=O)[O-])/n1cncn1
in ch i key: VKSOIYNNOFGGES-JYRVWZFOSA-N
in ch i: InChI=1S/C15H16N4O3/c1-15(2,3)14(20)13(18-10-16-9-17-18)8-11-5-4-6-12(7-11)19(21)22/h4-10H,1-3H3/b13-8-
comment: We have interpreted the image from <Reference id=31925/> as the Z form. Note there is also the E form as PubChem CID: 5759185 and a unresolved entry as PubChem CID: 2817394. Note this is an old compound (2005) from the Molecular Libraries screening collection and has many bioassay results (see ChEMBL entries) that were not assessed by the authors, so circumspection concerning pharmacological specificity is warranted.
iupac name: (Z)-4,4-dimethyl-1-(3-nitrophenyl)-2-(1,2,4-triazol-1-yl)pent-1-en-3-one
xref: CHEMBL1459140
approved: f
ligand name: Nexinhib20
type: SyntheticOrganicLigand

nusinersen
in ch i key: WWFDJIVIDXJAQR-FFWSQMGZSA-N
comment: Nusinersen (ISIS 396443) is an antisense oligo(ribo)nucleotide (ASO) which induces survival motor neuron (SMN) protein expression from SMN2 genes with the exon 7-skipping mutation <Reference id=31908/>. Nusinersen was initially available for use as a designated orphan drug (by the US FDA and EMA), and was the first drug to be fully approved for the treatment of spinal muscular atrophy (SMA). The sequence contains 2'-O-(2-methoxyethyl) (2'-MOE)-oligoribonucleotides to reduce nuclease degradation and enhance binding affinity towards the complementary RNA. The full sequence is [2'-O-(2-methoxyethyl)](3'-5')(P-thio)(mU-mC-A-mC-mU-mU-mU-mC-A-mU-A-A-mU-G-mC-mU-G-G) as detailed in the INN record for the agent. A full structural rendering using SMILES from Chemspider is available here (CSID:34983394). The sequence for nusinersen is claimed in patent WO2010148249A1 as SEQ ID NO: 1 <Reference id=31929/>.
synonym: ISIS 396443
synonym: Spinraza®
synonym: ASO-10-27
synonym: ISIS-SMNRx
synonym: Ionis-SMNrx
synonym: ISIS396443
approved: t
ligand name: nusinersen
type: SyntheticOrganicLigand

dehydroascorbic acid
canonical SMILES: OCC(C1OC(=O)C(=O)C1=O)O
isomeric SMILES: OC[C@@H]([C@H]1OC(=O)C(=O)C1=O)O
in ch i key: SBJKKFFYIZUCET-JLAZNSOCSA-N
in ch i: InChI=1S/C6H6O6/c7-1-2(8)5-3(9)4(10)6(11)12-5/h2,5,7-8H,1H2/t2-,5+/m0/s1
iupac name: (5R)-5-[(1S)-1,2-dihydroxyethyl]oxolane-2,3,4-trione
synonym: dehydroascorbate
approved: f
ligand name: dehydroascorbic acid
type: MetaboliteLigand

compound 11 [PMID: 15261275]
in ch i key: HHNAHVCOGFTMSQ-IRXDYDNUSA-N
comment: Compound 11 [PMID: 15261275] is a selective, nonpeptidic, small molecule antagonist of orexin receptor 2 (OX2R) <Reference id=5638/>. Such compounds are useful tools for investigating the physiological importance of OX2R, and in particular its role in modulating the sleep/wake cycle.
iupac name: 3-(4-bromo-2-chlorophenyl)-1-[(4S,5S)-2,2-dimethyl-4-phenyl-1,3-dioxan-5-yl]urea
xref: CHEMBL185088
approved: f
ligand name: compound 11 [PMID: 15261275]
type: SyntheticOrganicLigand

VLX1570
canonical SMILES: C=CC(=O)N1CCC(=Cc2ccc(c(c2)[N+](=O)[O-])F)C(=O)C(=Cc2ccc(c(c2)[N+](=O)[O-])F)C1
isomeric SMILES: C=CC(=O)N1CC/C(=C/c2ccc(c(c2)[N+](=O)[O-])F)/C(=O)/C(=C/c2ccc(c(c2)[N+](=O)[O-])F)/C1
in ch i key: SCKXBVLYWLLALY-CQRYCMKKSA-N
in ch i: InChI=1S/C23H17F2N3O6/c1-2-22(29)26-8-7-16(9-14-3-5-18(24)20(11-14)27(31)32)23(30)17(13-26)10-15-4-6-19(25)21(12-15)28(33)34/h2-6,9-12H,1,7-8,13H2/b16-9-,17-10-
comment: VLX1570 is a competitive, reversible inhibitor of 19S proteasome-specific deubiquitylating enzymes, including ubiquitin-specific protease-14 (USP14) and ubiquitin-C-terminal hydrolase-5 (UCHL5) <Reference id=31894/><Reference id=31893/>; being investigated for antineoplastic/antiproliferative efficacy.
iupac name: 1-acryloyl-3,5-bis((Z)-4-fluoro-3-nitrobenzylidene)azepan-4-one
synonym: VLX-1570
approved: f
ligand name: VLX1570
type: SyntheticOrganicLigand

[3H]7-OH-DPAT
canonical SMILES: CCCN(C1CCc2c(C1)cc(cc2)O)CCC
isomeric SMILES: CCCN(C1CCc2c(C1)cc(cc2)O)CCC
in ch i key: BLYMJBIZMIGWFK-UHFFFAOYSA-N
in ch i: InChI=1S/C16H25NO/c1-3-9-17(10-4-2)15-7-5-13-6-8-16(18)12-14(13)11-15/h6,8,12,15,18H,3-5,7,9-11H2,1-2H3
iupac name: 7-(dipropylamino)-5,6,7,8-tetrahydronaphthalen-2-ol
xref: CHEMBL285755
synonym: [3H]-7-OH-DPAT
approved: f
ligand name: [3H]7-OH-DPAT
type: SyntheticOrganicLigand

brensocatib
in ch i key: AEXFXNFMSAAELR-RXVVDRJESA-N
in ch i: InChI=1S/C23H24N4O4/c1-27-19-12-17(7-8-20(19)31-23(27)29)16-5-3-15(4-6-16)11-18(13-24)26-22(28)21-14-25-9-2-10-30-21/h3-8,12,18,21,25H,2,9-11,14H2,1H3,(H,26,28)/t18-,21-/m0/s1
comment: Brensocatib (formerly AZD7986) is reported as a second generation, oral, selective and reversible inhibitor of dipeptidyl peptidase 1 (DPP1; a.k.a. cathepsin C) <Reference id=31889/>. Cathepsin C is required for the activation of proinflammatory neutrophil serine proteases, making this enzyme a drug target whose pharmacological inhibition has potential in the treatment of diseases such as chronic obstructive pulmonary disease (COPD) which is driven in part by excessive neutrophil activation and dysregulated neutrophil elastase activity. The compound was originally developed by AstraZeneca, but is now being progressed by Insmed.
iupac name: (2S)-N-[(1S)-1-cyano-2-[4-(3-methyl-2-oxo-1,3-benzoxazol-5-yl)phenyl]ethyl]-1,4-oxazepane-2-carboxamide
synonym: INS 1007
synonym: INS1007
synonym: AZD7986
synonym: compound 30
approved: f
ligand name: brensocatib
type: SyntheticOrganicLigand

TH-4000E
in ch i key: QBACGOWRJDBXSG-ONEGZZNKSA-N
comment: TH-4000E is the active compound generated from the prodrug <Ligand id=9409/> (TH-4000).
iupac name: (2E)-N-{4-[(3-bromo-4-chlorophenyl)amino]pyrido[3,4-d]pyrimidin-6-yl}-4-(dimethylamino)but-2-enamide
approved: f
ligand name: TH-4000E
type: SyntheticOrganicLigand

tarloxotinib
in ch i key: MUJMYVFVAWFUJL-SNAWJCMRSA-O
comment: Tarloxotinib (TH-4000) is a hypoxia-activated prodrug (HAP) <Reference id=31884/> being developed by Threshold Pharmaceuticals. Delivered as the bromide salt (PubChem CID 51038315) as described in its INN record. The compound undergoes activation selectively within the hypoxic tumour compartment to produce an irreversible pan-ErbB tyrosine-kinase inhibitor, represented by <Ligand id=9410/> <Reference id=31884/>. The 4-nitroimidazole trigger on the tertiary amine side chain facilitates activation. This is one of the first molecularly targeted HAPs to be developed.
iupac name: [(E)-4-[[4-(3-bromo-4-chloroanilino)pyrido[3,4-d]pyrimidin-6-yl]amino]-4-oxobut-2-enyl]-dimethyl-[(3-methyl-5-nitroimidazol-4-yl)methyl]azanium
synonym: TH-4000
synonym: PR610
synonym: tarloxotinib cation
approved: f
ligand name: tarloxotinib
type: SyntheticOrganicLigand

EMD638683
in ch i key: SSNAPUUWBPZGOY-UHFFFAOYSA-N
in ch i: InChI=1S/C18H18F2N2O4/c1-3-13-9(2)15(23)5-4-14(13)17(25)21-22-18(26)16(24)10-6-11(19)8-12(20)7-10/h4-8,16,23-24H,3H2,1-2H3,(H,21,25)(H,22,26)
comment: EMD638683 is a small molecule tool compound which somewhat selectively inhibits serum/glucocorticoid regulated kinase 1 (SGK1) <Reference id=31870/>. We present the structure of EMD638683 without specified stereochemistry, as shown in this primary literature source.
iupac name: N'-[2-(3,5-difluorophenyl)-2-hydroxyacetyl]-2-ethyl-4-hydroxy-3-methylbenzohydrazide
approved: f
ligand name: EMD638683
type: SyntheticOrganicLigand

HG-10-102-01
in ch i key: YEVOZZZLKJKCCD-UHFFFAOYSA-N
in ch i: InChI=1S/C17H20ClN5O3/c1-19-15-12(18)10-20-17(22-15)21-13-4-3-11(9-14(13)25-2)16(24)23-5-7-26-8-6-23/h3-4,9-10H,5-8H2,1-2H3,(H2,19,20,21,22)
comment: HG-10-102-01 is a brain-penetrant, selective small-molecule inhibitor of LRRK2 (leucine rich repeat kinase 2), activating mutations of which have been associated with Parkinson's disease <Reference id=31845/>. An alternative stereoisomer is presented in <Reference id=31846/>.
xref: CHEMBL2170016
synonym: compound 15 [PMID: 22591441]
approved: f
ligand name: HG-10-102-01
type: SyntheticOrganicLigand

XMD17-109
in ch i key: XVBGRTMNFNMINE-UHFFFAOYSA-N
in ch i: InChI=1S/C36H46N8O3/c1-4-47-32-23-25(34(45)43-17-15-26(16-18-43)42-21-19-40(2)20-22-42)13-14-29(32)38-36-37-24-31-33(39-36)44(27-9-5-6-10-27)30-12-8-7-11-28(30)35(46)41(31)3/h7-8,11-14,23-24,26-27H,4-6,9-10,15-22H2,1-3H3,(H,37,38,39)
comment: XMD17-109 (ERK5-IN-1) is a potent and selective inhibitor of mitogen-activated protein kinase 7 (a.k.a. ERK5) <Reference id=31869/>, useful as a tool to investigate the ERK5 signalling pathway. It also inhibits bromodomains, with sufficient activity to explain all of the compound's reported biological effects.
iupac name: 11-cyclopentyl-2-[2-ethoxy-4-[4-(4-methylpiperazin-1-yl)piperidine-1-carbonyl]anilino]-5-methylpyrimido[4,5-b][1,4]benzodiazepin-6-one
xref: CHEMBL2381340
synonym: ERK5-IN-1
synonym: compound 26 [PMID: 24239623]
approved: f
ligand name: XMD17-109
type: SyntheticOrganicLigand

BS-181
in ch i key: DNYBIOICMDTDAP-UHFFFAOYSA-N
in ch i: InChI=1S/C22H32N6/c1-17(2)19-16-26-28-21(25-15-18-10-6-5-7-11-18)14-20(27-22(19)28)24-13-9-4-3-8-12-23/h5-7,10-11,14,16-17,25H,3-4,8-9,12-13,15,23H2,1-2H3,(H,24,27)
comment: BS-181 is a selective inhibitor of cyclin dependent kinase 7 (CDK7) with antitumour activity in vivo (human xenografts in nude mice) <Reference id=31868/>. Generally used as the hydrochloride salt (PubChem CID 49867928).
iupac name: 5-N-(6-aminohexyl)-7-N-benzyl-3-propan-2-ylpyrazolo[1,5-a]pyrimidine-5,7-diamine
xref: CHEMBL1801932
approved: f
ligand name: BS-181
type: SyntheticOrganicLigand

PP2
canonical SMILES: Clc1ccc(cc1)c1nn(c2c1c(N)ncn2)C(C)(C)C
isomeric SMILES: Clc1ccc(cc1)c1nn(c2c1c(N)ncn2)C(C)(C)C
in ch i key: PBBRWFOVCUAONR-UHFFFAOYSA-N
in ch i: InChI=1S/C15H16ClN5/c1-15(2,3)21-14-11(13(17)18-8-19-14)12(20-21)9-4-6-10(16)7-5-9/h4-8H,1-3H3,(H2,17,18,19)
comment: PP2 is a non-selective (pan) inhibitor of Src family tyrosine kinases, used widely to study the biological roles of Src kinases <Reference id=29920/>.
iupac name: 1-tert-butyl-3-(4-chlorophenyl)pyrazolo[4,5-e]pyrimidin-4-amine
xref: CHEMBL406845
approved: f
ligand name: PP2
type: SyntheticOrganicLigand

Ro3280
in ch i key: DJNZZLZKAXGMMC-UHFFFAOYSA-N
in ch i: InChI=1S/C27H35F2N7O3/c1-34-12-10-18(11-13-34)31-24(37)17-8-9-20(22(14-17)39-3)32-26-30-15-21-23(33-26)36(19-6-4-5-7-19)16-27(28,29)25(38)35(21)2/h8-9,14-15,18-19H,4-7,10-13,16H2,1-3H3,(H,31,37)(H,30,32,33)
comment: Ro3280 is a potent and selective inhibitor of Polo-like kinase 1 (PLK1) with antitumour activity in vivo (xenografts) <Reference id=31866/>.
iupac name: 4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8H-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-3-methoxy-N-(1-methylpiperidin-4-yl)benzamide
xref: CHEMBL2392553
synonym: compound 7 [PMID: 22172702]
synonym: RO3280
approved: f
ligand name: Ro3280
type: SyntheticOrganicLigand

MLN0905
in ch i key: CODBZFJPKJDNDT-UHFFFAOYSA-N
in ch i: InChI=1S/C24H25F3N6S/c1-14-19(9-15(12-28-14)5-4-8-33(2)3)31-23-29-13-16-10-21(34)30-20-11-17(24(25,26)27)6-7-18(20)22(16)32-23/h6-7,9,11-13H,4-5,8,10H2,1-3H3,(H,30,34)(H,29,31,32)
comment: MLN0905 is an orally bioavailable inhibitor of Polo-like kinase 1 (PLK1) with in vivo antitumour activity <Reference id=31865/>. Despite apparent off-target binding in a kinase profile screen, none of these targets would be expected to produce the cellular and pharmacodynamic effects associated with MLN0905, and in fact the phenotype observed with MLN0905 inhibition is consistent with that observed with PLK1 knockdown by RNAi and other PLK1 inhibitors.
iupac name: 2-[[5-[3-(dimethylamino)propyl]-2-methylpyridin-3-yl]amino]-9-(trifluoromethyl)-5,7-dihydropyrimido[5,4-d][1]benzazepine-6-thione
xref: CHEMBL1945805
synonym: compound 12c [PMID: 22070629]
approved: f
ligand name: MLN0905
type: SyntheticOrganicLigand

NMS-P715
in ch i key: JFOAJUGFHDCBJJ-UHFFFAOYSA-N
in ch i: InChI=1S/C35H39F3N8O3/c1-5-20-8-7-9-21(6-2)28(20)42-33(48)30-25-12-10-23-19-39-34(43-29(23)31(25)46(4)44-30)41-26-13-11-22(18-27(26)49-35(36,37)38)32(47)40-24-14-16-45(3)17-15-24/h7-9,11,13,18-19,24H,5-6,10,12,14-17H2,1-4H3,(H,40,47)(H,42,48)(H,39,41,43)
comment: NMS-P715 is an orally bioavailable, selective inhibitor of the mitotic kinase MPS1 (dual specificity protein kinase TTK; gene symbol TTK) <Reference id=31864/>. Studies showing NMS-P715-induced antitumour activity in vivo support MSP1 as a valid oncology drug target.
iupac name: N-(2,6-diethylphenyl)-1-methyl-8-[4-[(1-methylpiperidin-4-yl)carbamoyl]-2-(trifluoromethoxy)anilino]-4,5-dihydropyrazolo[4,3-h]quinazoline-3-carboxamide
xref: CHEMBL1236095
synonym: NMS P715
synonym: NMSP715
synonym: compound 15 [PMID: 21723120]
approved: f
ligand name: NMS-P715
type: SyntheticOrganicLigand

BIIB021
canonical SMILES: COc1c(C)cnc(c1C)Cn1cnc2c1nc(N)nc2Cl
isomeric SMILES: COc1c(C)cnc(c1C)Cn1cnc2c1nc(N)nc2Cl
in ch i key: QULDDKSCVCJTPV-UHFFFAOYSA-N
in ch i: InChI=1S/C14H15ClN6O/c1-7-4-17-9(8(2)11(7)22-3)5-21-6-18-10-12(15)19-14(16)20-13(10)21/h4,6H,5H2,1-3H3,(H2,16,19,20)
comment: This reference looks at the specificity of HSP90 inhibitors <Reference id=31355/>. BIIB021 exhibits antitumour activity in preclinical models, has maximum (2nM) potency against HSP90α (HSP90AA1) but cross-reacts between the four paralogues tested <Reference id=31355/>.
iupac name: 6-chloro-9-[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]purin-2-amine
xref: CHEMBL467399
approved: f
ligand name: BIIB021
type: SyntheticOrganicLigand

AZ3146
in ch i key: YUKWVHPTFRQHMF-UHFFFAOYSA-N
in ch i: InChI=1S/C24H32N6O3/c1-28-12-10-17(11-13-28)33-18-8-9-19(21(14-18)32-3)26-23-25-15-20-22(27-23)30(24(31)29(20)2)16-6-4-5-7-16/h8-9,14-17H,4-7,10-13H2,1-3H3,(H,25,26,27)
comment: AZ3146 is a selective inhibitor of the mitotic kinase MPS1 (dual specificity protein kinase TTK; gene symbol TTK) <Reference id=31863/>.
iupac name: 9-cyclopentyl-2-[2-methoxy-4-(1-methylpiperidin-4-yl)oxyanilino]-7-methylpurin-8-one
xref: CHEMBL2140523
approved: f
ligand name: AZ3146
type: SyntheticOrganicLigand

MPI-0479605
in ch i key: OVJBNYKNHXJGSA-UHFFFAOYSA-N
in ch i: InChI=1S/C22H29N7O/c1-15-13-17(29-9-11-30-12-10-29)7-8-18(15)26-22-27-20-19(23-14-24-20)21(28-22)25-16-5-3-2-4-6-16/h7-8,13-14,16H,2-6,9-12H2,1H3,(H3,23,24,25,26,27,28)
comment: MPI-0479605 is a selective, ATP-competitive inhibitor of the mitotic kinase MPS1 (dual specificity protein kinase TTK; gene symbol TTK) <Reference id=31862/>.
iupac name: 6-N-cyclohexyl-2-N-(2-methyl-4-morpholin-4-ylphenyl)-7H-purine-2,6-diamine
xref: CHEMBL2047943
approved: f
ligand name: MPI-0479605
type: SyntheticOrganicLigand

PHA-408
in ch i key: ZLEZHGHFWIHCGU-UHFFFAOYSA-N
comment: PHA-408 is a selective, ATP-competitive inhibitor of Iκβ kinase β (IKKβ a.k.a. IKK-2; gene symbol IKBKB) <Reference id=31855/><Reference id=31861/>, a drug target for asthma, chronic obstructive pulmonary disease (COPD) and arthritis.
iupac name: 8-[[5-chloro-2-(4-methylpiperazin-1-yl)pyridine-4-carbonyl]amino]-1-(4-fluorophenyl)-4,5-dihydrobenzo[g]indazole-3-carboxamide
xref: CHEMBL592893
synonym: PHA408
synonym: PHA- 408
approved: f
ligand name: PHA-408
type: SyntheticOrganicLigand

SNS-314
in ch i key: FAYAUAZLLLJJGH-UHFFFAOYSA-N
comment: SNS-314 is an inhibitor of Aurora kinases A and B <Reference id=31854/>. CHEMBL482767 represents an alternative tautomer of the compound.
iupac name: 1-(3-chlorophenyl)-3-[5-[2-(thieno[3,2-d]pyrimidin-4-ylamino)ethyl]-1,3-thiazol-2-yl]urea
synonym: SNS 314
synonym: SNS314
synonym: compound 21 [PMID: 18678489]
approved: f
ligand name: SNS-314
type: SyntheticOrganicLigand

LRRK2-IN-1
in ch i key: IWMCPJZTADUIFX-UHFFFAOYSA-N
in ch i: InChI=1S/C31H38N8O3/c1-35-15-17-38(18-16-35)22-11-13-39(14-12-22)29(40)21-9-10-24(27(19-21)42-4)33-31-32-20-26-28(34-31)36(2)25-8-6-5-7-23(25)30(41)37(26)3/h5-10,19-20,22H,11-18H2,1-4H3,(H,32,33,34)
comment: LRRK2-IN-1 is a selective inhibitor of the Parkinson's associated kinase LRRK2 (leucine rich repeat kinase 2) <Reference id=31853/>. The compound has limited brain penetrance. LRRK2-IN-1 is used as a pharmacological tool to interrogate the function of LRRK2 in Parkinson's disease.
iupac name: 2-[2-methoxy-4-[4-(4-methylpiperazin-1-yl)piperidine-1-carbonyl]anilino]-5,11-dimethylpyrimido[4,5-b][1,4]benzodiazepin-6-one
xref: CHEMBL2012582
synonym: LRRK2IN1
synonym: LRRK2-IN1
approved: f
ligand name: LRRK2-IN-1
type: SyntheticOrganicLigand

tofogliflozin
in ch i key: VWVKUNOPTJGDOB-BDHVOXNPSA-N
in ch i: InChI=1S/C22H26O6/c1-2-13-3-5-14(6-4-13)9-15-7-8-16-12-27-22(17(16)10-15)21(26)20(25)19(24)18(11-23)28-22/h3-8,10,18-21,23-26H,2,9,11-12H2,1H3/t18-,19-,20+,21-,22+/m1/s1
comment: Tofogliflozin is a selective sodium/glucose cotransporter 2 (SGLT2; SLC5A2) inhibitor <Reference id=31851/> (a 'gliflozin' family drug <Reference id=31847/>) developed as a treatment for type 2 diabetes. We show the anhydrous structure as represented in the INN record for tofogliflozin. In practice the drug is administered as the monohydrate (PubChem CID 46908928). Tofogliflozin has favourable oral bioavailability and pharmacokinetic profile <Reference id=31851/>.
iupac name: (3S,3'R,4'S,5'S,6'R)-5-[(4-ethylphenyl)methyl]-6'-(hydroxymethyl)spiro[1H-2-benzofuran-3,2'-oxane]-3',4',5'-triol
xref: CHEMBL2110731
synonym: CSG452
synonym: CSG 452
synonym: CSG-452
synonym: compound 16d [PMID: 22889351]
synonym: Apleway®
synonym: Deberza®
approved: t
ligand name: tofogliflozin
type: SyntheticOrganicLigand

ipragliflozin
in ch i key: AHFWIQIYAXSLBA-RQXATKFSSA-N
in ch i: InChI=1S/C21H21FO5S/c22-15-6-5-12(21-20(26)19(25)18(24)16(10-23)27-21)7-13(15)9-14-8-11-3-1-2-4-17(11)28-14/h1-8,16,18-21,23-26H,9-10H2/t16-,18-,19+,20-,21+/m1/s1
comment: Ipragliflozin is a selective and orally available sodium/glucose cotransporter 2 (SGLT2; SLC5A2) inhibitor <Reference id=31849/><Reference id=31850/> (a 'gliflozin' family drug <Reference id=31847/>) used to treat type 2 diabetes. In practice ipragliflozin is complexed with L-proline in a 1:1 ratio.
iupac name: (2S,3R,4R,5S,6R)-2-[3-(1-benzothiophen-2-ylmethyl)-4-fluorophenyl]-6-(hydroxymethyl)oxane-3,4,5-triol
xref: CHEMBL2018096
synonym: ASP-1941
synonym: ASP1941
synonym: ASP 1941
synonym: Suglat®
approved: t
ligand name: ipragliflozin
type: SyntheticOrganicLigand

GNE-0877
in ch i key: ZPPUMAMZIMPJGP-UHFFFAOYSA-N
in ch i: InChI=1S/C14H16F3N7/c1-8-10(6-24(23-8)13(2,3)7-18)21-12-20-5-9(14(15,16)17)11(19-4)22-12/h5-6H,1-4H3,(H2,19,20,21,22)
comment: GNE-0877 (renamed DNL201; Denali Therapeutics) is a potent and selective, brain penetrant small molecule inhibitor of LRRK2 (leucine-rich repeat kinase 2) <Reference id=43976/><Reference id=26199/>, a kinase whose aberrant activation is identified in a subset of patients with Parkinson's disease. LRRK2 ihnibitors are being developed as potential disease-modifying agents as therapeutics for Parkinson's disease.
iupac name: 2-methyl-2-[3-methyl-4-[[4-(methylamino)-5-(trifluoromethyl)pyrimidin-2-yl]amino]pyrazol-1-yl]propanenitrile
synonym: GNE0877
synonym: compound 11 [PMID: 24354345]
synonym: DNL-201
synonym: DNL201
approved: f
ligand name: GNE-0877
type: SyntheticOrganicLigand

compound 36 [PMID: 21958547]
in ch i key: KJDBCEWMSRFWQY-JXMROGBWSA-N
in ch i: InChI=1S/C24H31FN6O/c1-16-8-5-6-9-18(16)27-24-22-14-26-15-31(22)21-13-20(17(25)12-19(21)28-24)30(4)23(32)10-7-11-29(2)3/h5-10,14-15,17,19-21H,11-13H2,1-4H3,(H,27,28)/b10-7+
comment: Compound 36 is a selective and irreversible small molecule inhibitor of Bruton's tyrosine kinase (BTK) <Reference id=31844/>. The compound is being studied for potential to treat rheumatoid arthritis, having been assessed as effective in preclinical models of the disease.
approved: f
ligand name: compound 36 [PMID: 21958547]
type: SyntheticOrganicLigand

ceralasertib
in ch i key: OHUHVTCQTUDPIJ-JYCIKRDWSA-N
in ch i: InChI=1S/C20H24N6O2S/c1-13-12-28-10-9-26(13)17-11-16(20(5-6-20)29(2,21)27)24-19(25-17)15-4-8-23-18-14(15)3-7-22-18/h3-4,7-8,11,13,21H,5-6,9-10,12H2,1-2H3,(H,22,23)/t13-,29-/m1/s1
comment: Ceralasertib (AZD6738) is an orally available small molecule inhibitor of ATR serine/threonine kinase <Reference id=31843/><Reference id=36365/>. AZD6738 induces cell death and senescence in cancer cells in vitro and enhances the therapeutic efficacy of <Ligand id=5343/> in xenograft models. In vivo, combining AZD6738 with cisplatin destroys ATM-deficient lung cancer xenografts.
iupac name: (R)-imino(methyl)(1-{6-[(3R)-3-methylmorpholin-4-yl]-2-(1H-pyrrolo[2,3-b]pyridin-4-yl)pyrimidin-4-yl}cyclopropyl)-λ6-sulfanone
synonym: AZD-6738
synonym: AZD 6738
synonym: AZD6738
approved: f
ligand name: ceralasertib
type: SyntheticOrganicLigand

SB590885
in ch i key: DPCXEUSDRQOOGZ-YYADALCUSA-N
in ch i: InChI=1S/C27H27N5O2/c1-32(2)15-16-34-22-7-3-19(4-8-22)27-29-25(18-11-13-28-14-12-18)26(30-27)21-5-9-23-20(17-21)6-10-24(23)31-33/h3-5,7-9,11-14,17,28H,6,10,15-16H2,1-2H3,(H,29,30)/b26-21+
comment: SB590885 is a potent B-Raf inhibitor with 11-fold selectivity for B-Raf over c-Raf and no inhibition vs. other human kinases <Reference id=30903/>. It is reported to stabilise the open conformation of the enzyme <Reference id=31841/>.
iupac name: N,N-dimethyl-2-[4-[(4E)-4-(1-nitroso-2,3-dihydroinden-5-ylidene)-5-(1H-pyridin-4-ylidene)-1H-imidazol-2-yl]phenoxy]ethanamine
synonym: SB-590885
synonym: SB 590885
synonym: compound 33 [PMID: 16260133]
approved: f
ligand name: SB590885
type: SyntheticOrganicLigand

GSK143
in ch i key: KBPYMFSSFLOJPH-KGLIPLIRSA-N
in ch i: InChI=1S/C17H22N6O2/c1-10-2-4-11(5-3-10)21-16-12(15(19)24)8-20-17(23-16)22-14-6-7-25-9-13(14)18/h2-5,8,13-14H,6-7,9,18H2,1H3,(H2,19,24)(H2,20,21,22,23)/t13-,14+/m1/s1
comment: GSK143 a potent, selective and orally active spleen tyrosine kinase (SYK) inhibitor <Reference id=31837/> (compound 20 therein). It has favourable physicochemical properties including good aqueous solubility.
iupac name: 2-{[(3S,4S)-3-aminooxan-4-yl]amino}-4-[(4-methylphenyl)amino]pyrimidine-5-carboxamide
synonym: compound 20 [PMID: 21903390]
approved: f
ligand name: GSK143
type: SyntheticOrganicLigand

CEP-33779
in ch i key: RFZKSQIFOZZIAQ-UHFFFAOYSA-N
in ch i: InChI=1S/C24H26N6O2S/c1-28-13-15-29(16-14-28)20-6-3-5-19(17-20)25-24-26-23-22(7-4-12-30(23)27-24)18-8-10-21(11-9-18)33(2,31)32/h3-12,17H,13-16H2,1-2H3,(H,25,27)
comment: CEP-33779 is a selective, orally bioavailable inhibitor of Janus kinase 2 (JAK2) with anti-tumour activity <Reference id=31834/>. Selectivity for JAK2 over JAK3 is sought to minimise the risk of immune suppression associated with JAK3 inhibition.
iupac name: N-[3-(4-methylpiperazin-1-yl)phenyl]-8-(4-methylsulfonylphenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-amine
synonym: CEP33779
synonym: CEP 33779
synonym: compound 29 [PMID: 22594690]
approved: f
ligand name: CEP-33779
type: SyntheticOrganicLigand

BMS-536924
in ch i key: UGQMURPIMYALPH-UHFFFAOYSA-N
in ch i: InChI=1S/C25H26ClN5O3/c1-15-11-18(31-7-9-34-10-8-31)13-20-23(15)30-24(29-20)22-19(5-6-27-25(22)33)28-14-21(32)16-3-2-4-17(26)12-16/h2-6,11-13,21,28-30,32H,7-10,14H2,1H3
comment: BMS-536924 is an experimental inhbitor of insulin-like growth factor-1 receptor kinase which inhibits insulin-like growth factor-I receptor dependent tumour growth in vivo <Reference id=22565/>. However, its utility is hampered by its potential to cause drug-drug interactions via inhibition of CYP3A4, and ability to increase CYP3A4 protein expression <Reference id=31831/>.
synonym: compound 1 [PMID: 18763755]
synonym: compound 3 [PMID: 16134929]
synonym: BMS536924
synonym: BMS 536924
approved: f
ligand name: BMS-536924
type: SyntheticOrganicLigand

compound 18c [PMID: 25901531]
in ch i key: JYSLFQTWNRYWJT-UHFFFAOYSA-N
in ch i: InChI=1S/C17H20Cl2N6S/c1-10(2)21-4-3-5-25-16-14(15(20)22-9-23-16)24-17(25)26-13-7-11(18)6-12(19)8-13/h6-10,21H,3-5H2,1-2H3,(H2,20,22,23)
comment: HSP90B1 is involved in the regulation of a restricted number of proteins and represents a potential target in many diseases. In the reference for this entry 18c had IC50 of 220 nM, selectivity for HSP90B1 over other paralogs and biological activity in several cellular models of inflammation as well as cancer <Reference id=31265/>.
iupac name: 8-(3,5-dichlorophenyl)sulfanyl-9-[3-(propan-2-ylamino)propyl]purin-6-amine
xref: CHEMBL3426781
approved: f
ligand name: compound 18c [PMID: 25901531]
type: SyntheticOrganicLigand

OSI-930
in ch i key: FGTCROZDHDSNIO-UHFFFAOYSA-N
comment: OSI-930 is a multi-targeted kinase inhibitor, with potent inhibitory activity vs. Kit, KDR, CSF-1R, Flt1, c-Raf and Lck <Reference id=31830/>.
iupac name: 3-(quinolin-4-ylmethylamino)-N-[4-(trifluoromethoxy)phenyl]thiophene-2-carboxamide
xref: CHEMBL1614710
synonym: OSI930
synonym: OSI 930
approved: f
ligand name: OSI-930
type: SyntheticOrganicLigand

NVP-TAE 226
in ch i key: UYJNQQDJUOUFQJ-UHFFFAOYSA-N
in ch i: InChI=1S/C23H25ClN6O3/c1-25-22(31)16-5-3-4-6-18(16)27-21-17(24)14-26-23(29-21)28-19-8-7-15(13-20(19)32-2)30-9-11-33-12-10-30/h3-8,13-14H,9-12H2,1-2H3,(H,25,31)(H2,26,27,28,29)
comment: NVP-TAE 226 is an experimental, non-selective, ATP-competitive inhibitor of FAK (focal adhesion kinase; official name protein tyrosine kinase 2) <Reference id=31828/>. NVP-TAE 226 is not a selective compound and inhibits many other kinases in in vitro assays. An extended kinase selectivity profile for NVP-TAE 226 is provided in <Reference id=31829/>.
iupac name: 2-[[5-chloro-2-[(2-methoxy-4-morpholin-4-ylphenyl)amino]pyrimidin-4-yl]amino]-N-methylbenzamide
xref: CHEMBL458997
synonym: TAE 226
synonym: TAE226
synonym: NVP-TAE226
approved: f
ligand name: NVP-TAE 226
type: SyntheticOrganicLigand

PF-562271
in ch i key: MZDKLVOWGIOKTN-UHFFFAOYSA-N
comment: PF-562271 is an experimental ATP-competitive focal adhesion kinase (FAK; official name protein tyrosine kinase 2) inhibitor, designed to investigate the anti-tumour effects of FAK inhibition <Reference id=31827/>. Note that this compound may be used as the besylate (PubChem CID 16118986) as detailed in <Reference id=31827/>.
iupac name: N-methyl-N-[3-[[[2-[(2-oxo-1,3-dihydroindol-5-yl)amino]-5-(trifluoromethyl)pyrimidin-4-yl]amino]methyl]pyridin-2-yl]methanesulfonamide
xref: CHEMBL1084546
synonym: PF-562,271
synonym: PF-00562271
synonym: PF-562,271-26
approved: f
ligand name: PF-562271
type: SyntheticOrganicLigand

BIX02189
isomeric SMILES: CN(Cc1cccc(c1)N/C(=C/1/C(=O)Nc2c1ccc(c2)C(=O)N(C)C)/c1ccccc1)C
in ch i key: HOMJAAIVTDVQJA-IZHYLOQSSA-N
in ch i: InChI=1S/C27H28N4O2/c1-30(2)17-18-9-8-12-21(15-18)28-25(19-10-6-5-7-11-19)24-22-14-13-20(27(33)31(3)4)16-23(22)29-26(24)32/h5-16,28H,17H2,1-4H3,(H,29,32)/b25-24-
comment: BIX02189 is an experimental, small molecule inhibitor of mitogen-activated protein kinase kinase 5 (MEK5; MAP2K5) <Reference id=26633/>. It is more potent than <Ligand id=8064/>, described in the same article. Also inhibits ERK5 (MAPK7).
iupac name: (3Z)-3-[[3-[(dimethylamino)methyl]anilino]-phenylmethylidene]-N,N-dimethyl-2-oxo-1H-indole-6-carboxamide
synonym: BIX 02189
synonym: BIX-02189
approved: f
ligand name: BIX02189
type: SyntheticOrganicLigand

PIK-III
canonical SMILES: Nc1ncc(c(n1)CC1CC1)c1ccnc(n1)Nc1ccncc1
isomeric SMILES: Nc1ncc(c(n1)CC1CC1)c1ccnc(n1)Nc1ccncc1
in ch i key: XXSDLQLNIVFIJI-UHFFFAOYSA-N
in ch i: InChI=1S/C17H17N7/c18-16-21-10-13(15(23-16)9-11-1-2-11)14-5-8-20-17(24-14)22-12-3-6-19-7-4-12/h3-8,10-11H,1-2,9H2,(H2,18,21,23)(H,19,20,22,24)
comment: PIK-III is a selective inhibitor of VPS34 (PIK3C3) <Reference id=31826/>. PIK-III is used as a tool compound to investigate the role of VPS34 in autophagy and cellular homeostasis. SARS-CoV-2: PIK-III has been used in vitro to establish that VPS34 is required for SARS-CoV-2 replication <Reference id=42589/>.
iupac name: 4-(cyclopropylmethyl)-5-[2-(pyridin-4-ylamino)pyrimidin-4-yl]pyrimidin-2-amine
approved: f
ligand name: PIK-III
type: SyntheticOrganicLigand

VPS34-IN-1
in ch i key: AWNXKZVIZARMME-UHFFFAOYSA-N
in ch i: InChI=1S/C21H24ClN7O/c1-21(2,30)12-26-19-25-11-15(17(29-19)9-13-3-4-13)16-6-8-24-20(28-16)27-14-5-7-23-18(22)10-14/h5-8,10-11,13,30H,3-4,9,12H2,1-2H3,(H,25,26,29)(H,23,24,27,28)
comment: An inhibitor of the lipid kinase VPS34 (PIK3C3). VPS34-IN-1 is claimed as example 16a in patent US8685993 <Reference id=31824/>, which suggests that VPS34 inhibitors could be of use in treating hyperproliferative diseases characterized by hyperactivity of Vps34. SARS-CoV-2: VPS34-IN-1 has been used in vitro to establish that VPS34 is required for SARS-CoV-2 replication <Reference id=42589/>.
iupac name: 1-[[5-[2-[(2-chloropyridin-4-yl)amino]pyrimidin-4-yl]-4-(cyclopropylmethyl)pyrimidin-2-yl]amino]-2-methylpropan-2-ol
synonym: VPS34-IN1
synonym: example 16a [US8685993]
approved: f
ligand name: VPS34-IN-1
type: SyntheticOrganicLigand

JNK inhibitor 9l
in ch i key: AHMHIFXJPSHHPH-UHFFFAOYSA-N
in ch i: InChI=1S/C26H27FN8O2/c27-20-15-19(16-23(17-20)33-7-11-36-12-8-33)24-5-6-28-25(31-24)30-21-1-3-22(4-2-21)35-18-29-26(32-35)34-9-13-37-14-10-34/h1-6,15-18H,7-14H2,(H,28,30,31)
comment: JNK-9L is a selective and brain-penetrant c-jun-N-terminal kinase (JNK) inhibitor <Reference id=31823/>.
iupac name: 4-(3-fluoro-5-morpholin-4-ylphenyl)-N-[4-(3-morpholin-4-yl-1,2,4-triazol-1-yl)phenyl]pyrimidin-2-amine
xref: CHEMBL585951
synonym: JNK-9L
approved: f
ligand name: JNK inhibitor 9l
type: SyntheticOrganicLigand

IC-87114
in ch i key: GNWHRHGTIBRNSM-UHFFFAOYSA-N
in ch i: InChI=1S/C22H19N7O/c1-13-6-3-4-9-16(13)29-17(27-15-8-5-7-14(2)18(15)22(29)30)10-28-12-26-19-20(23)24-11-25-21(19)28/h3-9,11-12H,10H2,1-2H3,(H2,23,24,25)
comment: IC-87114 is a selective inhibitor of PI3Kδ <Reference id=23015/><Reference id=31821/>. Given that PI3Kδ is preferentially expressed in cells of hemopoietic lineage and is involved in neutrophil chemotaxis we have tagged this ligand as having immunopharmacology relevance. Using this chemical tool in in vitro chemotaxis experiments reveals that PI3Kδ activity is required for the directional component of chemotaxis, but is not required for random movement <Reference id=31821/>.
iupac name: 2-[(6-aminopurin-9-yl)methyl]-5-methyl-3-(2-methylphenyl)quinazolin-4-one
xref: CHEMBL1213082
synonym: IC87114
synonym: IC 87114
approved: f
ligand name: IC-87114
type: SyntheticOrganicLigand

KYT-0353
in ch i key: XNRZJPQTMQZBCE-SFHVURJKSA-N
comment: KYT-0353 (JPH203) is a potent and selective inhibitor of L-type amino acid transporter 1 (SLC7A5) <Reference id=31778/>, that is being investigated as an anti-cancer agent. Structurally it is a tyrosine analog.
iupac name: (2S)-2-amino-3-[4-[(5-amino-2-phenyl-1,3-benzoxazol-7-yl)methoxy]-3,5-dichlorophenyl]propanoic acid
synonym: JPH203
synonym: JPH-203
synonym: KYT 0353
synonym: KYT0353
synonym: COMPOUND-JP [US20160279103]
approved: f
ligand name: KYT-0353
type: SyntheticOrganicLigand

VTX-11e
in ch i key: WUTVMXLIGHTZJC-OAQYLSRUSA-N
comment: VTX-11e is a small molecule inhibitor of ERK2 developed by Vertex Pharmaceuticals <Reference id=31820/>. VTX-11e is orally active with a favourable pharmacokinetic profile.
iupac name: 4-[2-(2-chloro-4-fluoroanilino)-5-methylpyrimidin-4-yl]-N-[(1S)-1-(3-chlorophenyl)-2-hydroxyethyl]-1H-pyrrole-2-carboxamide
xref: CHEMBL583042
synonym: VX-11e
synonym: 11e [PMID: 19827834]
approved: f
ligand name: VTX-11e
type: SyntheticOrganicLigand

CX-5279
in ch i key: UXZATHOFDZQOMY-UHFFFAOYSA-M
in ch i: InChI=1S/C22H16F3N5O2/c23-22(24,25)12-2-1-3-14(9-12)27-19-18-16(10-26-21(30-18)28-13-5-6-13)15-7-4-11(20(31)32)8-17(15)29-19/h1-4,7-10,13H,5-6H2,(H,27,29)(H,31,32)(H,26,28,30)/p-1
comment: CX-5279 is a selective, small molecule, ATP-competitive (type I) inhibitor of casein kinase 2 (CK2), described in the same article as <Ligand id=8126/> and <Ligand id=9373/> <Reference id=31819/>
iupac name: 3-(cyclopropylamino)-5-[3-(trifluoromethyl)anilino]pyrimido[4,5-c]quinoline-8-carboxylate
approved: f
ligand name: CX-5279
type: SyntheticOrganicLigand

CX-5011
in ch i key: HJGFPNFAFSFDNN-UHFFFAOYSA-M
in ch i: InChI=1S/C20H12N4O2/c1-2-12-4-3-5-14(8-12)23-19-18-16(10-21-11-22-18)15-7-6-13(20(25)26)9-17(15)24-19/h1,3-11H,(H,23,24)(H,25,26)/p-1
comment: CX-5011 is a selective, small molecule, ATP-competitive (type I) inhibitor of casein kinase 2 (CK2), described in the same article as <Ligand id=8126/> and <Ligand id=9374/> <Reference id=31819/>.
iupac name: 5-(3-ethynylanilino)pyrimido[4,5-c]quinoline-8-carboxylate
approved: f
ligand name: CX-5011
type: SyntheticOrganicLigand

TBBt
canonical SMILES: Brc1c(Br)c(Br)c2c(c1Br)n[nH]n2
isomeric SMILES: Brc1c(Br)c(Br)c2c(c1Br)n[nH]n2
in ch i key: OMZYUVOATZSGJY-UHFFFAOYSA-N
in ch i: InChI=1S/C6HBr4N3/c7-1-2(8)4(10)6-5(3(1)9)11-13-12-6/h(H,11,12,13)
comment: TBBt is a small molecule ATP-competitive inhibitor of casein kinase 2 (CK2). It is used as a comparator to novel compounds in <Reference id=31818/>.
iupac name: 4,5,6,7-tetrabromo-2H-benzotriazole
xref: CHEMBL177820
synonym: TBB
synonym: Casein Kinase II Inhibitor I
approved: f
ligand name: TBBt
type: SyntheticOrganicLigand

PF-670462
canonical SMILES: Nc1nccc(n1)c1n(cnc1c1ccc(cc1)F)C1CCCCC1
isomeric SMILES: Nc1nccc(n1)c1n(cnc1c1ccc(cc1)F)C1CCCCC1
in ch i key: WUDBUIUHVNECTM-UHFFFAOYSA-N
in ch i: InChI=1S/C19H20FN5/c20-14-8-6-13(7-9-14)17-18(16-10-11-22-19(21)24-16)25(12-23-17)15-4-2-1-3-5-15/h6-12,15H,1-5H2,(H2,21,22,24)
comment: We show the parent molecule of PF-670462 here. It is described in the original literature report as the dihydrochloride salt (PubChem CID 51049607) <Reference id=31816/>. PF-670462 is a selective inhibitor of casein kinase I epsilon (CKIε).
iupac name: 4-[3-cyclohexyl-5-(4-fluorophenyl)imidazol-4-yl]pyrimidin-2-amine
xref: CHEMBL1951415
approved: f
ligand name: PF-670462
type: SyntheticOrganicLigand

BPKDi
in ch i key: XNWDRALEEPGBHB-UHFFFAOYSA-N
in ch i: InChI=1S/C21H28N6O/c22-21(28)16-12-18(26-20(14-16)27-10-8-23-9-11-27)15-6-7-24-19(13-15)25-17-4-2-1-3-5-17/h6-7,12-14,17,23H,1-5,8-11H2,(H2,22,28)(H,24,25)
comment: BPKDi inhibits all three protein kinase D isozymes at low nanomolar concentrations <Reference id=31814/>. This tool compound has been used to show that PKD acts to phosphorylate class IIa histone deacetylases in cardiomyocytes during cardiac hypertrophy. Inhibition of this action by BPKDi suppresses cardiomyocyte hypertrophy.
iupac name: 2-[2-(cyclohexylamino)pyridin-4-yl]-6-piperazin-1-ylpyridine-4-carboxamide
xref: CHEMBL1214999
synonym: bipyridyl PKD inhibitor
approved: f
ligand name: BPKDi
type: SyntheticOrganicLigand

kb-NB142-70
canonical SMILES: Oc1cc2c3SCCNC(=O)c3sc2cc1
isomeric SMILES: Oc1cc2c3SCCNC(=O)c3sc2cc1
in ch i key: DHUAGGSHTKPOHU-UHFFFAOYSA-N
in ch i: InChI=1S/C11H9NO2S2/c13-6-1-2-8-7(5-6)9-10(16-8)11(14)12-3-4-15-9/h1-2,5,13H,3-4H2,(H,12,14)
comment: kb-NB142-70 is a protein kinase D tool compound inhibitor <Reference id=31813/>.
iupac name: 9-hydroxy-3,4-dihydro-2H-[1]benzothiolo[2,3-f][1,4]thiazepin-5-one
xref: CHEMBL1672571
synonym: kb NB 142-70
approved: f
ligand name: kb-NB142-70
type: SyntheticOrganicLigand

CX-6258
isomeric SMILES: CN1CCCN(CC1)C(=O)c1cccc(c1)c1ccc(o1)/C=C/1/C(=O)Nc2c1cc(Cl)cc2
in ch i key: KGBPLKOPSFDBOX-CJLVFECKSA-N
in ch i: InChI=1S/C26H24ClN3O3/c1-29-10-3-11-30(13-12-29)26(32)18-5-2-4-17(14-18)24-9-7-20(33-24)16-22-21-15-19(27)6-8-23(21)28-25(22)31/h2,4-9,14-16H,3,10-13H2,1H3,(H,28,31)/b22-16+
comment: CX-6258 is a non-selective but potent small molecule inhibitor of the PIM serine/threonine kinases <Reference id=31812/>.
iupac name: (3E)-5-chloro-3-[[5-[3-(4-methyl-1,4-diazepane-1-carbonyl)phenyl]furan-2-yl]methylidene]-1H-indol-2-one
xref: CHEMBL2037200
synonym: CX6258
synonym: CX 6258
synonym: compound 13 [PMID: 24900437]
approved: f
ligand name: CX-6258
type: SyntheticOrganicLigand

LGB321
in ch i key: ODZZYKUYGVLOTQ-ONJZCGHCSA-N
in ch i: InChI=1S/C23H22F3N5O2/c1-12-10-31(11-16(27)22(12)32)19-7-8-28-9-18(19)30-23(33)17-6-5-15(26)21(29-17)20-13(24)3-2-4-14(20)25/h2-9,12,16,22,32H,10-11,27H2,1H3,(H,30,33)/t12-,16+,22+/m0/s1
comment: LGB321 is a biochemically non-selective inhibitor of PIM serine/threonine kinases <Reference id=31811/>. In cells, LGB321 is antiproliferative on PIM2-dependent multiple myeloma cells.
iupac name: N-[4-[(3R,4R,5S)-3-amino-4-hydroxy-5-methylpiperidin-1-yl]pyridin-3-yl]-6-(2,6-difluorophenyl)-5-fluoropyridine-2-carboxamide
xref: CHEMBL3105022
approved: f
ligand name: LGB321
type: SyntheticOrganicLigand

MELK-TI
in ch i key: GMZCYCKIXQZORP-UHFFFAOYSA-N
in ch i: InChI=1S/C21H22N4O2/c1-27-20-11-15(17-12-23-24-13-17)3-5-19(20)21(26)25-18-4-2-14-6-8-22-9-7-16(14)10-18/h2-5,10-13,22H,6-9H2,1H3,(H,23,24)(H,25,26)
comment: MELK-T1 is a small-molecule tool compound inhibitor of maternal embryonic leucine zipper kinase (MELK) <Reference id=31809/>, a serine/threonine protein kinase overexpressed in many cancer cells.
iupac name: 2-methoxy-4-(1H-pyrazol-4-yl)-N-(2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl)benzamide
xref: CHEMBL3355059
synonym: compound 7 [PMID: 25589925]
approved: f
ligand name: MELK-TI
type: SyntheticOrganicLigand

CHIR-124
in ch i key: VBIIUHUSFOLTIU-LJQANCHMSA-N
in ch i: InChI=1S/C23H22ClN5O/c24-14-5-6-16-15(11-14)21(25-19-12-29-9-7-13(19)8-10-29)20(23(30)28-16)22-26-17-3-1-2-4-18(17)27-22/h1-6,11,13,19,25-27H,7-10,12H2/t19-/m1/s1
comment: CHIR-124 is a potent cell permeable checkpoint kinase 1 (CHK1) inhibitor tool compound <Reference id=31808/>.
iupac name: 4-[[(3S)-1-azabicyclo[2.2.2]octan-3-yl]amino]-6-chloro-3-(1,3-dihydrobenzimidazol-2-ylidene)quinolin-2-one
xref: CHEMBL377312
synonym: CHIR124
synonym: CHIR 124
synonym: compound 11 [PMID: 6603354]
approved: f
ligand name: CHIR-124
type: SyntheticOrganicLigand

rimacalib
isomeric SMILES: N/C(=N/c1onc(c1)[C@H](c1ccc(c(c1)F)c1ccccc1)C)/N1CCOCC1
in ch i key: MYTIJGWONQOOLC-HNNXBMFYSA-N
in ch i: InChI=1S/C22H23FN4O2/c1-15(17-7-8-18(19(23)13-17)16-5-3-2-4-6-16)20-14-21(29-26-20)25-22(24)27-9-11-28-12-10-27/h2-8,13-15H,9-12H2,1H3,(H2,24,25)/t15-/m0/s1
comment: Rimacalib (SMP-114) is an isoxazole derivative inhibitor of Ca2+/calmodulin-dependent protein kinase II (CaMKII) <Reference id=31807/>, CAMKII being an established pharmacological target for chronic inflammatory pain <Reference id=31806/>, as well as being involved in modulating synaptic plasticity and learning and memory processes.
iupac name: N'-[3-[(1S)-1-(3-fluoro-4-phenylphenyl)ethyl]-1,2-oxazol-5-yl]morpholine-4-carboximidamide
xref: CHEMBL2107772
synonym: SMP 114
synonym: SMP-114
approved: f
ligand name: rimacalib
type: SyntheticOrganicLigand

BU72
in ch i key: RGJHUVJQGAAZLK-GKTFKBBASA-N
in ch i: InChI=1S/C28H32N2O2/c1-25-17-26-11-12-28(25,32-3)24(29-23(25)18-7-5-4-6-8-18)27(26)13-14-30(2)22(26)15-19-9-10-20(31)16-21(19)27/h4-12,16,22-24,29,31H,13-15,17H2,1-3H3/t22-,23-,24+,25+,26-,27+,28+/m1/s1
comment: BU72 was reported as a long-lasting μ receptor agonist <Reference id=31802/>. Its very high affinity meant that it was not considered as a clinical candidate. Strong lipophilic binding interactions with the μ receptor confer slow receptor kinetics, and therefore long duration of action. We revised the chemical structure in March 2021, based on data arising from analysis of the crystal structure of the BU72/μ receptor complex that was deposited to the Protein Data Bank (5C1M) <Reference id=41569/><Reference id=41573/>. This shows that the (β-phenyl) group of BU72 shoud be in the (R) configuration. BU72 has been used in a number of studies to model the μ receptor activation process <Reference id=41571/><Reference id=41572/>.
iupac name: (2R,3S,3aR,5aR,6R,11bR,11cS)-3a-methoxy-3,14-dimethyl-2-phenyl-2,3,3a,6,7,11c-hexahydro-1H-6,11b-(epiminoethano)-3,5a-methanonaphtho[2,1-g]indol-10-ol
synonym: compound 10 (Husbands and Lewis, 1995)
approved: f
ligand name: BU72
type: SyntheticOrganicLigand

AZD7545
in ch i key: DTDZLJHKVNTQGZ-GOSISDBHSA-N
comment: AZD7545 is a non-ATP competitive inhibitor of pyruvate dehydrogenase kinase 2 (PDHK2), designed for its glucose-lowering (anti-diabetes) activity <Reference id=31801/>.
iupac name: 4-[3-chloro-4-[[(2R)-3,3,3-trifluoro-2-hydroxy-2-methylpropanoyl]amino]phenyl]sulfonyl-N,N-dimethylbenzamide
synonym: AZD 7545
synonym: AZD-7545
approved: f
ligand name: AZD7545
type: SyntheticOrganicLigand

WYE-354
in ch i key: IMXHGCRIEAKIBU-UHFFFAOYSA-N
in ch i: InChI=1S/C24H29N7O5/c1-34-23(32)26-17-5-3-16(4-6-17)20-27-21(29-11-13-36-14-12-29)19-15-25-31(22(19)28-20)18-7-9-30(10-8-18)24(33)35-2/h3-6,15,18H,7-14H2,1-2H3,(H,26,32)
comment: WYE-354 is a pyrazolopyrimidine ATP-competitive mTOR inhibitor tool compound <Reference id=31800/>.
iupac name: methyl 4-[6-[4-(methoxycarbonylamino)phenyl]-4-morpholin-4-ylpyrazolo[3,4-d]pyrimidin-1-yl]piperidine-1-carboxylate
xref: CHEMBL561708
synonym: WYE 354
synonym: WYE354
approved: f
ligand name: WYE-354
type: SyntheticOrganicLigand

PXS-4728A
canonical SMILES: NCC(=CF)COc1ccc(cc1)C(=O)NC(C)(C)C
isomeric SMILES: NC/C(=C/F)/COc1ccc(cc1)C(=O)NC(C)(C)C
in ch i key: OWNSXNXYELKDSO-DHZHZOJOSA-N
in ch i: InChI=1S/C15H21FN2O2/c1-15(2,3)18-14(19)12-4-6-13(7-5-12)20-10-11(8-16)9-17/h4-8H,9-10,17H2,1-3H3,(H,18,19)/b11-8+
comment: VAP-1/SSAO (gene symbol AOC3) is an endothelial bound adhesion molecule with amine oxidase activity that is reported to be involved in neutrophil egress from the microvasculature during inflammation. The primary reference <Reference id=31776/> indicates the potential of inhibiting this enzyme using PXS-4728A, as a therapeutic approach in lung diseases that are characterized by a neutrophilic pattern of inflammation. A more recent paper reports PXS-4728A-mediated suppression of airway inflammation and fibrosis, as well as improved lung function in experimental COPD <Reference id=31777/>. Thirty nine analogues are exemplified in <Reference id=31782/> but without discrete activity values.
iupac name: 4-[(E)-2-(aminomethyl)-3-fluoroprop-2-enoxy]-N-tert-butylbenzamide
synonym: PXS4728A
approved: f
ligand name: PXS-4728A
type: SyntheticOrganicLigand

KU-0063794
in ch i key: RFSMUFRPPYDYRD-CALCHBBNSA-N
in ch i: InChI=1S/C25H31N5O4/c1-16-13-30(14-17(2)34-16)25-27-23-20(24(28-25)29-8-10-33-11-9-29)5-6-21(26-23)18-4-7-22(32-3)19(12-18)15-31/h4-7,12,16-17,31H,8-11,13-15H2,1-3H3/t16-,17+
comment: KU-0063794 is a selective inhibitor of mammalian target of rapamycin (mTOR) <Reference id=31799/>. It inhibits both mTORC1 and mTORC2 with an IC50 of ~10 nM.
iupac name: [5-[2-[(2R,6S)-2,6-dimethylmorpholin-4-yl]-4-morpholin-4-ylpyrido[5,6-e]pyrimidin-7-yl]-2-methoxyphenyl]methanol
xref: CHEMBL1078983
synonym: KU0063794
synonym: KU-63794
synonym: Ku 0063794
synonym: Ku63794
approved: f
ligand name: KU-0063794
type: SyntheticOrganicLigand

CP466722
canonical SMILES: COc1cc2c(cc1OC)ncnc2n1nc(nc1N)c1ccccn1
isomeric SMILES: COc1cc2c(cc1OC)ncnc2n1nc(nc1N)c1ccccn1
in ch i key: ILBRKJBKDGCSCB-UHFFFAOYSA-N
in ch i: InChI=1S/C17H15N7O2/c1-25-13-7-10-12(8-14(13)26-2)20-9-21-16(10)24-17(18)22-15(23-24)11-5-3-4-6-19-11/h3-9H,1-2H3,(H2,18,22,23)
comment: CP466722 is a selective and reversible small molecule tool compound inhibitor of ATM serine/threonine kinase <Reference id=31798/>. ATM is a PI3K family kinase, implicated in the DNA damage response (DDR) pathway.
iupac name: 2-(6,7-dimethoxyquinazolin-4-yl)-5-pyridin-2-yl-1,2,4-triazol-3-amine
xref: CHEMBL2143829
synonym: CP-466722
synonym: CP 466722
approved: f
ligand name: CP466722
type: SyntheticOrganicLigand

FMK
in ch i key: IKLGYJACVCXYIL-UHFFFAOYSA-N
in ch i: InChI=1S/C18H19FN4O2/c1-11-3-5-12(6-4-11)14-15-17(20)21-10-22-18(15)23(7-2-8-24)16(14)13(25)9-19/h3-6,10,24H,2,7-9H2,1H3,(H2,20,21,22)
comment: FMK is an irreversible inhibitor of ribosomal protein S6 kinases (RSKs) <Reference id=22985/>. It binds covalently to the regulatory C-terminal kinase domain of the enzyme, thereby inhibiting activation of the N-terminal kinase domain.
xref: CHEMBL515414
synonym: FMK (covalent)
approved: f
ligand name: FMK
type: SyntheticOrganicLigand

BI605906
in ch i key: IYHHRZBKXXKDDY-UHFFFAOYSA-N
comment: BI605906 is an inhibitor of IKKβ (IKBKB) <Reference id=26630/>. Inhibitors of the kinase activity of the IκB kinase (IKK) complex are in development as novel therapeutics for IKK mediated diseases including autoimmune, inflammatory and cardiovascular diseases, and cancer. A chemical series inluding this structure is claimed in patent US20070293533 <Reference id=31797/>. BI605906 was tested in preclinical studies.
iupac name: 3-amino-4-(1,1-difluoropropyl)-6-(4-methylsulfonylpiperidin-1-yl)thieno[5,4-b]pyridine-2-carboxamide
synonym: compound 115 [US20070293533]
synonym: 3-Amino-4-(1,1-difluoro- propyl)-6-(4-methanesulfonyl- piperidin-1-yl)-thieno[2,3- b]pyridine-2-carboxylic acid amide
approved: f
ligand name: BI605906
type: SyntheticOrganicLigand

GSK429286A
in ch i key: OLIIUAHHAZEXEX-UHFFFAOYSA-N
in ch i: InChI=1S/C21H16F4N4O2/c1-10-19(20(31)28-17-6-12-9-26-29-16(12)8-15(17)22)14(7-18(30)27-10)11-2-4-13(5-3-11)21(23,24)25/h2-6,8-9,14H,7H2,1H3,(H,26,29)(H,27,30)(H,28,31)
comment: GSK429286A is a selective small molecule tool inhibitor of Rho kinase 1 (ROCK1) <Reference id=31796/>.
iupac name: N-(6-fluoro-1H-indazol-5-yl)-6-methyl-2-oxo-4-[4-(trifluoromethyl)phenyl]-3,4-dihydro-1H-pyridine-5-carboxamide
xref: CHEMBL375312
synonym: compound 15 [PMID: 17201405]
approved: f
ligand name: GSK429286A
type: SyntheticOrganicLigand

GNE-3511
in ch i key: RHFIAUKMKYHHFA-UHFFFAOYSA-N
in ch i: InChI=1S/C23H26F2N6O/c24-23(25)4-8-31(15-23)22-11-18(17-2-6-30(7-3-17)19-13-32-14-19)10-21(29-22)28-20-9-16(12-26)1-5-27-20/h1,5,9-11,17,19H,2-4,6-8,13-15H2,(H,27,28,29)
comment: GNE-3511 is an inhibitor of dual leucine zipper kinase (DLK; MAP3K12), investigated for therapeutic potential in neurodegenerative conditions <Reference id=31795/>. It is potent and most importantly, it can cross the blood-brain-barrier to access neuronal tissue. It was tested in preclinical studies.
iupac name: 2-[[6-(3,3-difluoropyrrolidin-1-yl)-4-[1-(oxetan-3-yl)piperidin-4-yl]pyridin-2-yl]amino]pyridine-4-carbonitrile
xref: CHEMBL3393333
synonym: GNE3511
synonym: GNE 3511
synonym: compound 26 [PMID: 25341110]
approved: f
ligand name: GNE-3511
type: SyntheticOrganicLigand

D-cysteine
canonical SMILES: NC(C(=O)O)CS
isomeric SMILES: N[C@@H](C(=O)O)CS
in ch i key: XUJNEKJLAYXESH-UWTATZPHSA-N
in ch i: InChI=1S/C3H7NO2S/c4-2(1-7)3(5)6/h2,7H,1,4H2,(H,5,6)/t2-/m1/s1
iupac name: (2S)-2-amino-3-sulfanylpropanoic acid
xref: CHEMBL171281
approved: f
ligand name: D-cysteine
type: MetaboliteLigand

DDR-IN-1
in ch i key: AOZPVMOOEJAZGK-UHFFFAOYSA-N
in ch i: InChI=1S/C30H31F3N4O3/c1-3-36-10-12-37(13-11-36)18-21-6-5-20(15-25(21)30(31,32)33)29(39)34-23-7-4-19(2)27(17-23)40-24-8-9-26-22(14-24)16-28(38)35-26/h4-9,14-15,17H,3,10-13,16,18H2,1-2H3,(H,34,39)(H,35,38)
comment: DDR-IN-1 is a potent and selective discoidin domain receptor tyrosine kinase 1 (DDR1) inhibitor <Reference id=31793/>. DDR1-IN-1 binds to DDR1 in the 'DFG-out' conformation and inhibits DDR1 autophosphorylation. It was a preclinical lead compound.
xref: CHEMBL3421914
approved: f
ligand name: DDR-IN-1
type: SyntheticOrganicLigand

SAR405
in ch i key: SPDQRCUBFSRAFI-DOMZBBRYSA-N
comment: SAR405 is a small molecule inhibitor selective for the lipid kinase, vacuolar protein sorting 34 (Vps34; PIK3C3), a kinase with roles in autophagy and vesicle trafficking <Reference id=31792/>. It was tested in preclinical studies.
iupac name: (8S)-9-[(5-chloropyridin-3-yl)methyl]-2-[(3R)-3-methylmorpholin-4-yl]-8-(trifluoromethyl)-7,8-dihydro-6H-pyrimido[1,2-a]pyrimidin-4-one
xref: CHEMBL3622372
synonym: SAR-405
synonym: SAR 405
approved: f
ligand name: SAR405
type: SyntheticOrganicLigand

harmine
canonical SMILES: COc1ccc2c(c1)[nH]c1c2ccnc1C
isomeric SMILES: COc1ccc2c(c1)[nH]c1c2ccnc1C
in ch i key: BXNJHAXVSOCGBA-UHFFFAOYSA-N
in ch i: InChI=1S/C13H12N2O/c1-8-13-11(5-6-14-8)10-4-3-9(16-2)7-12(10)15-13/h3-7,15H,1-2H3
comment: Harmine is a plant-derived β-carboline alkaloid that has psychoactive activity. It has been reported as an inhibitor of dual specificity tyrosine phosphorylation regulated kinases of the Dyrk1 subfamily <Reference id=26948/><Reference id=31791/> and monoamine oxidase A <Reference id=38851/><Reference id=38852/><Reference id=38853/>. Harmine has been tested in preclincal studies for antidepressant potential <Reference id=38850/>
iupac name: 7-Methoxy-1-methyl-9H-pyrido[3,4-b]indole
approved: f
ligand name: harmine
type: NaturalProductLigand

MLCK inhibitor peptide 18
in ch i key: JPOKAKNGULMYHZ-UILVTTEASA-N
comment: This nine amino acid peptide was designed as a selective inhibitor of myosin light chain kinase (MLCK) <Reference id=31790/>. It was tested in preclinical studies.
xref: CHEMBL443574
synonym: Myosin Light Chain Kinase Inhibitor Peptide 18
approved: f
ligand name: MLCK inhibitor peptide 18
type: PeptideLigand

L779450
in ch i key: WXJLXRNWMLWVFB-UHFFFAOYSA-N
in ch i: InChI=1S/C20H14ClN3O/c21-16-7-6-15(12-17(16)25)19-18(13-8-10-22-11-9-13)23-20(24-19)14-4-2-1-3-5-14/h1-12,25H,(H,23,24)
comment: L779450 is a potent ATP competitive inhibitor of RAF kinases <Reference id=30903/><Reference id=30902/>, with potential antineoplastic activity.
iupac name: 2-chloro-5-(2-phenyl-5-pyridin-4-yl-1H-imidazol-4-yl)phenol
xref: CHEMBL373011
synonym: L-779,450
synonym: compound 1 [PMID:18346893]
synonym: L-779450
synonym: compound 2 [PMID: 16260133]
approved: f
ligand name: L779450
type: SyntheticOrganicLigand

VER-246608
in ch i key: LCGNLQSOSJFLKR-UHFFFAOYSA-N
comment: VER-246608 is a potent, selective and ATP-competitive, pan-isoform inhibitor of pyruvate dehydrogenase kinases (PDKs)<Reference id=31789/>. Analysis of VER-246608 activity suggests that PDK inhibitors may be most effective within the nutrient-depleted tumour microenvironment, and may potentiate the activity of other chemotherapeutic agents.
approved: f
ligand name: VER-246608
type: SyntheticOrganicLigand

compound 41 [PMID: 25000588]
in ch i key: OUZPGLCFBNPQPF-MRVPVSSYSA-N
in ch i: InChI=1S/C16H18F3N5O2/c1-8-14(25)23-22-13-5-26-12-3-9(16(17,18)19)10(4-11(12)24(8)13)21-15(2)6-20-7-15/h3-4,8,20-21H,5-7H2,1-2H3,(H,23,25)/t8-/m1/s1
comment: Compound 41 [PMID: 25000588] is a selective and orally active inhibitor of protein kinase Cθ (PKCθ), identified using structure-based drug design <Reference id=31788/>. PKCθ is a drug target for autoimmune diseases including rheumatoid arthritis (RA), inflammatory bowel disease (IBD), and psoriasis. It was tested in preclinical studies.
iupac name: (1R)-1-methyl-9-[(3-methylazetidin-3-yl)amino]-8-(trifluoromethyl)-3,5-dihydro-1H-[1,2,4]triazino[3,4-c][1,4]benzoxazin-2-one
approved: f
ligand name: compound 41 [PMID: 25000588]
type: SyntheticOrganicLigand

compound 5 [PMID: 17618114]
in ch i key: SINQIEAULQKUPD-UHFFFAOYSA-N
in ch i: InChI=1S/C26H21N3O2S/c1-31-22-8-5-19-15-21(4-3-20(19)16-22)25-24(17-11-13-27-14-12-17)28-26(29-25)18-6-9-23(10-7-18)32(2)30/h3-16H,1-2H3,(H,28,29)
comment: Compound 5 [PMID: 17618114] is an inhibitor of TEK receptor tyrosine kinase (a.k.a. TIE2) <Reference id=31787/>. Compound 5 was SAR optimised from lead <Ligand id=5269/>. Small molecule Tie2 inhibitors are being developed for potential use as anti-angiogenic cancer therapeutics.
xref: CHEMBL237352
synonym: Tie2 kinase inhibitor
approved: f
ligand name: compound 5 [PMID: 17618114]
type: SyntheticOrganicLigand

deslorelin
in ch i key: GJKXGJCSJWBJEZ-XRSSZCMZSA-N
in ch i: InChI=1S/C64H83N17O12/c1-4-68-62(92)53-16-10-24-81(53)63(93)46(15-9-23-69-64(65)66)74-56(86)47(25-35(2)3)75-58(88)49(27-37-30-70-43-13-7-5-11-41(37)43)77-57(87)48(26-36-17-19-40(83)20-18-36)76-61(91)52(33-82)80-59(89)50(28-38-31-71-44-14-8-6-12-42(38)44)78-60(90)51(29-39-32-67-34-72-39)79-55(85)45-21-22-54(84)73-45/h5-8,11-14,17-20,30-32,34-35,45-53,70-71,82-83H,4,9-10,15-16,21-29,33H2,1-3H3,(H,67,72)(H,68,92)(H,73,84)(H,74,86)(H,75,88)(H,76,91)(H,77,87)(H,78,90)(H,79,85)(H,80,89)(H4,65,66,69)/t45-,46-,47-,48-,49+,50-,51-,52-,53-/m0/s1
comment: GnRH peptide agonist
iupac name: (2S)-N-[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2R)-1-[[(2S)-1-[[(2S)-5-(diaminomethylideneamino)-1-[(2S)-2-(ethylcarbamoyl)pyrrolidin-1-yl]-1-oxopentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-3-(4-hydroxyphenyl)-1-oxopropan-2-yl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-3-(1H-imidazol-5-yl)-1-oxopropan-2-yl]-5-oxopyrrolidine-2-carboxamide
approved: f
ligand name: deslorelin
type: PeptideLigand

alarelin
in ch i key: QLGKMLRGKPKGKI-QWQCQAQZSA-N
in ch i: InChI=1S/C56H78N16O12/c1-5-60-54(83)45-13-9-21-72(45)55(84)39(12-8-20-61-56(57)58)66-50(79)40(22-30(2)3)67-47(76)31(4)64-49(78)41(23-32-14-16-35(74)17-15-32)68-53(82)44(28-73)71-51(80)42(24-33-26-62-37-11-7-6-10-36(33)37)69-52(81)43(25-34-27-59-29-63-34)70-48(77)38-18-19-46(75)65-38/h6-7,10-11,14-17,26-27,29-31,38-45,62,73-74H,5,8-9,12-13,18-25,28H2,1-4H3,(H,59,63)(H,60,83)(H,64,78)(H,65,75)(H,66,79)(H,67,76)(H,68,82)(H,69,81)(H,70,77)(H,71,80)(H4,57,58,61)/t31-,38+,39+,40+,41+,42+,43+,44+,45+/m1/s1
comment: GnRH peptide agonist
iupac name: (2S)-N-[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2R)-1-[[(2S)-1-[[(2S)-5-(diaminomethylideneamino)-1-[(2S)-2-(ethylcarbamoyl)pyrrolidin-1-yl]-1-oxopentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-1-oxopropan-2-yl]amino]-3-(4-hydroxyphenyl)-1-oxopropan-2-yl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-3-(3H-imidazol-4-yl)-1-oxopropan-2-yl]-5-oxopyrrolidine-2-carboxamide
approved: f
ligand name: alarelin
type: PeptideLigand

chlorobenzylidene malononitrile
canonical SMILES: N#CC(=Cc1ccccc1Cl)C#N
isomeric SMILES: N#CC(=Cc1ccccc1Cl)C#N
in ch i key: JJNZXLAFIPKXIG-UHFFFAOYSA-N
in ch i: InChI=1S/C10H5ClN2/c11-10-4-2-1-3-9(10)5-8(6-12)7-13/h1-5H
xref: CHEMBL1256101
synonym: 2-chlorobenzylidene malononitrile
synonym: alonitrile
synonym: CS gas (lacrimator)
approved: f
ligand name: chlorobenzylidene malononitrile
type: SyntheticOrganicLigand

fertirelin
in ch i key: DGCPIBPDYFLAAX-YTAGXALCSA-N
in ch i: InChI=1S/C55H76N16O12/c1-4-59-53(82)44-12-8-20-71(44)54(83)38(11-7-19-60-55(56)57)66-49(78)39(21-30(2)3)65-46(75)27-62-47(76)40(22-31-13-15-34(73)16-14-31)67-52(81)43(28-72)70-50(79)41(23-32-25-61-36-10-6-5-9-35(32)36)68-51(80)42(24-33-26-58-29-63-33)69-48(77)37-17-18-45(74)64-37/h5-6,9-10,13-16,25-26,29-30,37-44,61,72-73H,4,7-8,11-12,17-24,27-28H2,1-3H3,(H,58,63)(H,59,82)(H,62,76)(H,64,74)(H,65,75)(H,66,78)(H,67,81)(H,68,80)(H,69,77)(H,70,79)(H4,56,57,60)/t37-,38-,39-,40-,41-,42-,43-,44-/m0/s1
comment: GnRH peptide agonist
iupac name: (2S)-N-[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[2-[[(2S)-1-[[(2S)-5-(diaminomethylideneamino)-1-[(2S)-2-(ethylcarbamoyl)pyrrolidin-1-yl]-1-oxopentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-2-oxoethyl]amino]-3-(4-hydroxyphenyl)-1-oxopropan-2-yl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-3-(3H-imidazol-4-yl)-1-oxopropan-2-yl]-5-oxopyrrolidine-2-carboxamide
approved: f
ligand name: fertirelin
type: PeptideLigand

AM6538
in ch i key: KXXKUWQMQUYUSE-UHFFFAOYSA-N
comment: AM6538 is a cannabinoid CB1 receptor antagonist, used to stabilise the receptor-ligand complex for crystalisation studies <Reference id=31764/>. AM6538 is a derivative of <Ligand id=3317/>, a widely used <Ligand id=743/> analogue.
iupac name: 4-{4-[1-(2,4-dichlorophenyl)-4-methyl-3-[(piperidin-1-yl)carbamoyl]-1H-pyrazol-5-yl]phenyl}but-3-yn-1-yl nitrate
synonym: 4-(4-(1-(2,4-dichlorophenyl)-4-methyl-3-(piperidin-1-ylcarbamoyl)-1 H-pyrazol-5- yl)phenyl)but-3-ynyl nitrate
synonym: compound 10 [WO2010104488]
synonym: Example 2 [WO2010104488]
approved: f
ligand name: AM6538
type: SyntheticOrganicLigand

TCS 1102
in ch i key: YSBGRVXJEMSEQY-DEOSSOPVSA-N
in ch i: InChI=1S/C27H26N4O2S/c1-30-23-15-8-7-14-22(23)29-27(30)34-18-25(32)31-17-9-16-24(31)26(33)28-21-13-6-5-12-20(21)19-10-3-2-4-11-19/h2-8,10-15,24H,9,16-18H2,1H3,(H,28,33)/t24-/m0/s1
comment: TCS 1102 is a dual orexin antagonist, with potent in vivo central activity in a pharmacodynamic model of orexin activity <Reference id=31588/>.
iupac name: (2S)-1-[2-(1-methylbenzimidazol-2-yl)sulfanylacetyl]-N-(2-phenylphenyl)pyrrolidine-2-carboxamide
xref: CHEMBL429848
synonym: TCS-1102
synonym: BBAC
synonym: compound 18 [PMID: 18207395]
approved: f
ligand name: TCS 1102
type: SyntheticOrganicLigand

compound 3 [PMID: 27347366]
in ch i key: PHXSVGGLTIKXSW-GUZVZUIYSA-N
in ch i: InChI=1S/C37H50N4O5/c1-6-14-32(42)34(36(45)39-23-25(2)3)38-24-33(43)31(21-27-15-9-7-10-16-27)40-35(44)29-19-13-20-30(22-29)37(46)41(5)26(4)28-17-11-8-12-18-28/h7-13,15-20,22,25-26,31-34,38,42-43H,6,14,21,23-24H2,1-5H3,(H,39,45)(H,40,44)/t26-,31+,32+,33-,34+/m1/s1
comment: Inhibitor 3 showed potent BACE2 inhibitory activity, ~174,000-fold selectivity over BACE1 and ~15,000-fold selectivity over Cathepsin D <Reference id=31755/>. Note the PDB structure 5DQC is a co-crystalisation with comound 2 as PubChem CID 89836206 Inhibitor 3 is described in a patent as example 6412 <Reference id=31756/>. Activity data is included for ~30 analogues.
iupac name: 1-N-[(2S,3R)-3-hydroxy-4-[[(2S,3S)-3-hydroxy-1-(2-methylpropylamino)-1-oxohexan-2-yl]amino]-1-phenylbutan-2-yl]-3-N-methyl-3-N-[(1R)-1-phenylethyl]benzene-1,3-dicarboxamide
synonym: Compound 6412 from US9096541
approved: f
ligand name: compound 3 [PMID: 27347366]
type: SyntheticOrganicLigand

FR900359
in ch i key: IMXKHFILKMPFGB-ZWYWTTNJSA-N
in ch i: InChI=1S/C49H75N7O15/c1-17-34(58)52-35(39(59)24(2)3)47(65)70-40(25(4)5)36-46(64)56(15)38(30(11)68-16)49(67)71-41(26(6)7)37(51-31(12)57)48(66)69-33(23-32-21-19-18-20-22-32)45(63)55(14)28(9)42(60)50-27(8)44(62)54(13)29(10)43(61)53-36/h18-22,24-27,29-30,33,35-41,59H,9,17,23H2,1-8,10-16H3,(H,50,60)(H,51,57)(H,52,58)(H,53,61)/t27-,29-,30+,33+,35-,36-,37-,38-,39+,40+,41+/m0/s1
comment: FR900359 from the plant Ardisia crenata is a specific inhibitor of Gq and an analogue of <Ligand id=9335/>. A recent report describes the total synthesis of FR900359 and analogues with SAR <Reference id=33022/>. Note that structures with assay results are indexed in the Nature Chemistry paper as PubChem substances.
iupac name: [(1R)-1-[(3S,6S,9S,12S,18R,21S,22R)-21-acetamido-18-benzyl-3-[(1R)-1-methoxyethyl]-4,9,10,12,16-pentamethyl-15-methylidene-2,5,8,11,14,17,20-heptaoxo-22-propan-2-yl-1,19-dioxa-4,7,10,13,16-pentazacyclodocos-6-yl]-2-methylpropyl] (2S,3R)-3-hydroxy-4-methyl-2-(propanoylamino)pentanoate
approved: f
ligand name: FR900359
type: SyntheticOrganicLigand

ponesimod
isomeric SMILES: CCCN=C1S/C(=C/c2ccc(c(c2)Cl)OC[C@@H](CO)O)/C(=O)N1c1ccccc1C
in ch i key: LPAUOXUZGSBGDU-ULCCENQXSA-N
comment: Ponesimod (ACT-128800) is an orally active sphingosine-1-phosphate (S1P) receptor modulator <Reference id=31714/> that was developed as a disease-modifying therapy (DMT) for multiple sclerosis (MS). The compound is reported as a partial S1P4 and S1P5 receptor agonist, with maximum activity 18% and 42% of that induced by the endogenous ligand S1P (at 10μM ACT-128800) <Reference id=31714/>. The INN record for ponesimod stipulates the (2R) stereoisomer ((2Z,5Z)-5-{3-chloro-4-[(2R)-2,3-dihydroxypropoxy]phenylmethylidene}-3-(2-methylphenyl)-2-(propylimino)-1,3-thiazolidin-4-one). Selective SIP1 receptor agonists are being developed and investigated for immunomodulatory/immunosuppressant potential in autoimmune diseases.
iupac name: (5Z)-5-[[3-chloro-4-[(2R)-2,3-dihydroxypropoxy]phenyl]methylidene]-3-(2-methylphenyl)-2-propylimino-1,3-thiazolidin-4-one
xref: CHEMBL1096146
synonym: ACT-128800
synonym: ACT128800
synonym: ACT 128800
synonym: Compound 8bo [PMID:20446681]
synonym: Ponvory®
approved: t
ligand name: ponesimod
type: SyntheticOrganicLigand

YM-254890
in ch i key: QVYLWCAYZGFGNF-WBWCVGBTSA-N
in ch i: InChI=1S/C46H69N7O15/c1-22(2)37(56)34(49-30(11)55)45(63)68-38(23(3)4)35-43(61)53(14)36(28(9)65-15)46(64)66-27(8)33(48-29(10)54)44(62)67-32(21-31-19-17-16-18-20-31)42(60)52(13)25(6)39(57)47-24(5)41(59)51(12)26(7)40(58)50-35/h16-20,22-24,26-28,32-38,56H,6,21H2,1-5,7-15H3,(H,47,57)(H,48,54)(H,49,55)(H,50,58)/t24-,26-,27+,28+,32+,33-,34-,35-,36-,37+,38+/m0/s1
comment: The natural product YM-254890 from Chromobacterium sp. QS3666 is a selective inhibitor of Gq signalling. The first total synthesis of this and analogues with SAR are reported <Reference id=31754/>. Note that PubChem substances with assay results are indexed in the Nature Chemistry article. An earlier PDB entry 3AH8 shows a bovine G-protein complex with YM-254890.
iupac name: [(1R)-1-[(3S,6S,9S,12S,18R,21S,22R)-21-acetamido-3-[(1R)-1-methoxyethyl]-4,9,10,12,16,22-hexamethyl-15-methylidene-2,5,8,11,14,17,20-heptaoxo-18-(phenylmethyl)-1,19-dioxa-4,7,10,13,16-pentazacyclodocos-6-yl]-2-methylpropyl] (2S,3R)-2-acetamido-3-hydroxy-4-methylpentanoate
synonym: YM254890
approved: f
ligand name: YM-254890
type: NaturalProductLigand

RWJ-56423
in ch i key: VXDAVYUFYPFGDX-SNPRPXQTSA-N
in ch i: InChI=1S/C20H26N6O4S/c1-11(27)26-10-12(28)9-15(26)18(30)24-14(6-4-8-23-20(21)22)17(29)19-25-13-5-2-3-7-16(13)31-19/h2-3,5,7,12,14-15,28H,4,6,8-10H2,1H3,(H,24,30)(H4,21,22,23)/t12-,14+,15+/m1/s1
comment: RWJ-56423 is an inhibitor of human mast cell tryptase (TPSAB1) <Reference id=31749/>. Such compounds have therapeutic potential for treating allergic or inflammatory disorders.
iupac name: (2S,4R)-1-acetyl-N-[(2S)-1-(1,3-benzothiazol-2-yl)-5-(diaminomethylideneamino)-1-oxopentan-2-yl]-4-hydroxypyrrolidine-2-carboxamide
xref: CHEMBL256892
synonym: (2S)-6
approved: f
ligand name: RWJ-56423
type: SyntheticOrganicLigand

JQEZ5
in ch i key: LQTWDAYNGMMHLV-UHFFFAOYSA-N
in ch i: InChI=1S/C30H38N8O2/c1-6-7-21-14-20(4)34-30(40)24(21)17-32-29(39)23-15-26(35-28-25(23)18-33-38(28)19(2)3)22-8-9-27(31-16-22)37-12-10-36(5)11-13-37/h8-9,14-16,18-19H,6-7,10-13,17H2,1-5H3,(H,32,39)(H,34,40)
comment: JQEZ5 is a potent and selective inhibitor of the histone methyltransferase EZH2 (enhancer of zeste 2 polycomb repressive complex 2 subunit) <Reference id=31745/><Reference id=31746/><Reference id=31748/>. A commonly identified somatic gain-of-function mutation in human EZH2 (Y646F), recapitulated in a mouse model (Y641F) induces tumourigenesis by massively redistributing repressive trimethylated Lys27 histone H3 marks, leading to altered repression and activation of polycomb-regulated loci. JQEZ5 was developed at the Dana-Farber Cancer Institute and is openly available as a research probe.
iupac name: N-[(6-methyl-2-oxo-4-propyl-1H-pyridin-3-yl)methyl]-6-[6-(4-methylpiperazin-1-yl)pyridin-3-yl]-1-propan-2-ylpyrazolo[3,4-b]pyridine-4-carboxamide
synonym: EZ-005
synonym: JQ5
synonym: EZ005
synonym: JQE5
approved: f
ligand name: JQEZ5
type: SyntheticOrganicLigand

etrasimod
in ch i key: MVGWUTBTXDYMND-QGZVFWFLSA-N
in ch i: InChI=1S/C26H26F3NO3/c27-26(28,29)22-11-15(5-8-19(22)16-3-1-2-4-16)14-33-18-7-10-23-21(13-18)20-9-6-17(12-24(31)32)25(20)30-23/h5,7-8,10-11,13,16-17,30H,1-4,6,9,12,14H2,(H,31,32)/t17-/m1/s1
comment: Etrasimod (APD334) is a centrally available, selective S1P1 receptor agonist <Reference id=31744/>. APD334 is being investigated for clinical efficacy as an immunosuppressant for the treatment of autoimmune diseases.
iupac name: 2-[(3R)-7-[[4-cyclopentyl-3-(trifluoromethyl)phenyl]methoxy]-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl]acetic acid
xref: CHEMBL3358920
synonym: APD334
synonym: APD-334
synonym: compound 4 [PMID: 25516790]
synonym: APD334-003
approved: f
ligand name: etrasimod
type: SyntheticOrganicLigand

CDP840
in ch i key: UTUUPXBCDMQYRR-HSZRJFAPSA-N
in ch i: InChI=1S/C25H27NO2/c1-27-24-12-11-21(18-25(24)28-22-9-5-6-10-22)23(20-7-3-2-4-8-20)17-19-13-15-26-16-14-19/h2-4,7-8,11-16,18,22-23H,5-6,9-10,17H2,1H3/t23-/m1/s1
comment: CPD840 is a potent, competitive, orally active, and selective inhibitor of all four PDE4 isoenzymes <Reference id=31739/>. It was developed primarily for potential anti-inflammatory effects in asthma and chronic obstructive pulmonary disease (COPD) <Reference id=24358/>. The compound is now available for repurposing via the MRC-Industry Asset Sharing Initiative 2016 (full compound list).
iupac name: 4-[(2R)-2-(3-cyclopentyloxy-4-methoxyphenyl)-2-phenylethyl]pyridine
xref: CHEMBL32442
synonym: CDP 840
synonym: CDP-840
approved: f
ligand name: CDP840
type: SyntheticOrganicLigand

TAK-637
in ch i key: LDXQLWNPGRANTO-GOSISDBHSA-N
in ch i: InChI=1S/C30H25F6N3O2/c1-17-5-7-20(8-6-17)24-23-4-3-10-37-25(23)27(40)39-11-9-18(2)15-38(28(41)26(24)39)16-19-12-21(29(31,32)33)14-22(13-19)30(34,35)36/h3-8,10,12-14,18H,9,11,15-16H2,1-2H3/t18-/m1/s1
comment: TAK-637 was developed as a tachykinin 1 (NK1) receptor antagonist, and identified as a clinical candidate for the treatment of bladder function disorders <Reference id=31736/><Reference id=31738/>. TAK-637 is now available for repurposing via the MRC-Industry Asset Sharing Initiative 2016 (full compound list).
iupac name: (9R)-7-[[3,5-bis(trifluoromethyl)phenyl]methyl]-9-methyl-5-(4-methylphenyl)-8,9,10,11-tetrahydro-[1,4]diazocino[2,1-g][1,7]naphthyridine-6,13-dione
xref: CHEMBL339486
synonym: TAK 637
synonym: TAK637
synonym: compound (aR,9R)-8b [PMID: 10508446]
approved: f
ligand name: TAK-637
type: SyntheticOrganicLigand

TAK-715
in ch i key: HEKAIDKUDLCBRU-UHFFFAOYSA-N
in ch i: InChI=1S/C24H21N3OS/c1-3-21-27-22(18-11-7-8-16(2)14-18)23(29-21)19-12-13-25-20(15-19)26-24(28)17-9-5-4-6-10-17/h4-15H,3H2,1-2H3,(H,25,26,28)
comment: TAK-715 was developed as a p38 MAP kinase inhibitor, with anti-TNFα activity of potential clinical use as an anti-rheumatoid arthritis (RA) agent <Reference id=31735/>. TAK-715 is now available for repurposing via the MRC-Industry Asset Sharing Initiative 2016 (full compound list).
iupac name: N-[4-[2-ethyl-4-(3-methylphenyl)-1,3-thiazol-5-yl]pyridin-2-yl]benzamide
xref: CHEMBL363648
synonym: TAK 715
synonym: compound 8h [PMID: 16162000]
synonym: TAK0715
approved: f
ligand name: TAK-715
type: SyntheticOrganicLigand

verinurad
canonical SMILES: N#Cc1ccc(c2c1cccc2)c1cnccc1SC(C(=O)O)(C)C
isomeric SMILES: N#Cc1ccc(c2c1cccc2)c1cnccc1SC(C(=O)O)(C)C
in ch i key: YYBOLPLTQDKXPM-UHFFFAOYSA-N
in ch i: InChI=1S/C20H16N2O2S/c1-20(2,19(23)24)25-18-9-10-22-12-17(18)16-8-7-13(11-21)14-5-3-4-6-15(14)16/h3-10,12H,1-2H3,(H,23,24)
comment: Verinurad (RDEA3170) is an investigational selective uric acid reabsorption inhibitor, functionally inhibiting the URAT1 (SLC22A12) transporter and being investigated for clinical efficacy in controlling uric acid levels in patients with gout. URAT1 is the renal transporter that regulates uric acid excretion from the body. Verinurad is structurally related to <Ligand id=7673/> (RDEA594), a URAT1 inhibitor already approved for treating hyperuricemia in gout.
iupac name: 2-[3-(4-cyanonaphthalen-1-yl)pyridin-4-yl]sulfanyl-2-methylpropanoic acid
synonym: RDEA3170
synonym: RDEA-3170
approved: f
ligand name: verinurad
type: SyntheticOrganicLigand

abediterol
in ch i key: SFYAXIFVXBKRPK-QFIPXVFZSA-N
in ch i: InChI=1S/C25H30F2N2O4/c26-25(27,18-8-4-3-5-9-18)17-33-15-7-2-1-6-14-28-16-22(31)19-10-12-21(30)24-20(19)11-13-23(32)29-24/h3-5,8-13,22,28,30-31H,1-2,6-7,14-17H2,(H,29,32)/t22-/m0/s1
comment: Abediterol (AS100977) is an investigational long-acting beta(β)-agonist (LABA) <Reference id=31733/>, in development as a once-daily treatment for asthma <Reference id=31732/> and potentially COPD. Currently available LABAs approved for use by asthmatic patients include <Ligand id=559/>, <Ligand id=3465/> and <Ligand id=7543/>.
iupac name: 5-[(1R)-2-[6-(2,2-difluoro-2-phenylethoxy)hexylamino]-1-hydroxyethyl]-8-hydroxy-1H-quinolin-2-one
xref: CHEMBL3039530
synonym: LAS-100977
approved: f
ligand name: abediterol
type: SyntheticOrganicLigand

ACT-462206
in ch i key: NHPQGZOBHSVTAQ-IBGZPJMESA-N
in ch i: InChI=1S/C20H24N2O4S/c1-14-11-15(2)13-16(12-14)21-20(23)19-5-4-10-22(19)27(24,25)18-8-6-17(26-3)7-9-18/h6-9,11-13,19H,4-5,10H2,1-3H3,(H,21,23)/t19-/m0/s1
comment: ACT-462206 is an orally active, potent, brain-penetrant dual orexin 1/orexin 2 receptor antagonist <Reference id=31586/>. ACT-462206 is being developed by Actelion Pharmaceuticals for clinical potential as a sleep disorder therapeutic.
iupac name: (2S)-N-(3,5-dimethylphenyl)-1-(4-methoxyphenyl)sulfonylpyrrolidine-2-carboxamide
synonym: compound 24 [PMID: 25147058]
approved: f
ligand name: ACT-462206
type: SyntheticOrganicLigand

velsecorat
in ch i key: ZZWJKLGCDHYVMB-BWGXUDETSA-N
in ch i: InChI=1S/C32H32F2N4O6/c1-19(36-31(40)32(2,33)34)29(20-6-9-27-28(16-20)43-13-12-42-27)44-25-7-8-26-22(15-25)17-35-38(26)24-5-3-4-21(14-24)30(39)37-23-10-11-41-18-23/h3-9,14-17,19,23,29H,10-13,18H2,1-2H3,(H,36,40)(H,37,39)/t19-,23+,29-/m0/s1
comment: Velsecorat (AZD7594) is a novel non-steroidal modulator of inflammation <Reference id=33666/>. Functionally it is a selective glucocorticoid receptor modulator (SGRM) delivered by inhalation, that was being developed for asthma and COPD <Reference id=33666/>. Stereoisomers with 3S and 3R configuration at the bond with the tetrahydrofuran group are claimed in patent US8916600 (Examples 5 and 6 respectively) <Reference id=31731/>. AZD7594 is identified as the 1R,2S,3′R stereoisomer in <Reference id=33666/>.
iupac name: 3-{5-[(1R,2S)-2-(2,2-difluoropropanamido)-1-(2,3-dihydro-1,4-benzodioxin-6-yl)propoxy]-1H-indazol-1-yl}-N-[(3R)-oxolan-3-yl]benzamide
xref: CHEMBL3666807
synonym: compound 15m [PMID: 28937774]
synonym: AZD7594
synonym: AZ13189620
approved: f
ligand name: velsecorat
type: SyntheticOrganicLigand

DMAT
canonical SMILES: CN(c1[nH]c2c(n1)c(Br)c(c(c2Br)Br)Br)C
isomeric SMILES: CN(c1[nH]c2c(n1)c(Br)c(c(c2Br)Br)Br)C
in ch i key: SLPJGDQJLTYWCI-UHFFFAOYSA-N
in ch i: InChI=1S/C9H7Br4N3/c1-16(2)9-14-7-5(12)3(10)4(11)6(13)8(7)15-9/h1-2H3,(H,14,15)
comment: DMAT is a potent cell permeable inhibitor of casein kinase 2 (CK2) <Reference id=31727/><Reference id=31723/>.
iupac name: 4,5,6,7-TETRABROMO-N,N-DIMETHYL-1H-BENZIMIDAZOL-2-AMINE
xref: CHEMBL376505
synonym: CK2 Inhibitor II
synonym: 2-Dimethylamino-4,5,6,7-tetrabromo-1H-benzimidazole
approved: f
ligand name: DMAT
type: SyntheticOrganicLigand

netarsudil
in ch i key: OURRXQUGYQRVML-AREMUKBSSA-N
in ch i: InChI=1S/C28H27N3O3/c1-18-3-10-25(19(2)13-18)28(33)34-17-20-4-6-21(7-5-20)26(15-29)27(32)31-24-9-8-23-16-30-12-11-22(23)14-24/h3-14,16,26H,15,17,29H2,1-2H3,(H,31,32)/t26-/m1/s1
comment: Netarsudil (AR-11324) is a combination Rho-associated protein kinase (Rho or ROCK) and norepinephrine transporter (NET) inhibitor <Reference id=33968/><Reference id=31721/>. Netarsudil is the S-enantiomeric, 2,4-dimethyl benzoate ester of compound 29 (Ki 0.2nM) described in <Reference id=31721/>. Esterification improves bioavailability and corneal penetrating ability of the compound. It is an ocular hypotensive medication.
iupac name: [4-[(2S)-3-amino-1-(isoquinolin-6-ylamino)-1-oxopropan-2-yl]phenyl]methyl 2,4-dimethylbenzoate
synonym: Rhokiinsa®
synonym: AR-11324
synonym: AR 11324
synonym: AR11324
synonym: ester 60 [PMID: 27072905]
synonym: Rhopressa®
approved: t
ligand name: netarsudil
type: SyntheticOrganicLigand

amiselimod
canonical SMILES: CCCCCCCOc1ccc(cc1C(F)(F)F)CCC(CO)(CO)N
isomeric SMILES: CCCCCCCOc1ccc(cc1C(F)(F)F)CCC(CO)(CO)N
in ch i key: JVCPIJKPAKAIIP-UHFFFAOYSA-N
in ch i: InChI=1S/C19H30F3NO3/c1-2-3-4-5-6-11-26-17-8-7-15(12-16(17)19(20,21)22)9-10-18(23,13-24)14-25/h7-8,12,24-25H,2-6,9-11,13-14,23H2,1H3
comment: Amiselimod (MT-1303) is claimed in patent US20090137530 (Compound 1-3 is the hydrochloride used experimentally) as a potential immunomodulatory agent <Reference id=31713/>. It is a sphingosine-1-phosphate (SIP) receptor prodrug agonist, similar in action to the approved MS drug <Ligand id=2407/>, but with improved receptor subtype selectivity <Reference id=32464/>. Selective SIP1 receptor agonists are being investigated for immunomodulatory/immunosuppresant action in MS and other autoimmune conditions <Reference id=31528/>.
iupac name: 2-amino-2-[2-[4-heptoxy-3-(trifluoromethyl)phenyl]ethyl]propane-1,3-diol
synonym: MT-1303
synonym: MT1303
synonym: MT 1303
synonym: Example 1 [US20090137530]
approved: f
ligand name: amiselimod
type: SyntheticOrganicLigand

RA-2
in ch i key: XOZKRECPKXTNAK-UHFFFAOYSA-N
in ch i: InChI=1S/C22H16F2O6/c23-17-9-15(4-6-19(17)25)21(27)29-11-13-2-1-3-14(8-13)12-30-22(28)16-5-7-20(26)18(24)10-16/h1-10,25-26H,11-12H2
comment: Pan-negative-gating modulator of KCa2/3 channels.
iupac name: {3-[(3-fluoro-4-hydroxybenzoyloxy)methyl]phenyl}methyl 3-fluoro-4-hydroxybenzoate
approved: f
ligand name: RA-2
type: SyntheticOrganicLigand

NS13001
in ch i key: DVQOPNIPUIOXHU-UHFFFAOYSA-N
in ch i: InChI=1S/C17H16ClN7/c1-10-8-11(2)25(23-10)17-21-15(14-16(22-17)24(3)9-19-14)20-13-6-4-12(18)5-7-13/h4-9H,1-3H3,(H,20,21,22)
comment: Selective positive modulator of KCa2/3 channels.
iupac name: N-(4-chlorophenyl)-2-(3,5-dimethylpyrazol-1-yl)-9-methylpurin-6-amine
approved: f
ligand name: NS13001
type: SyntheticOrganicLigand

B-TPMF
in ch i key: HJKSIPKXGWOSBM-UHFFFAOYSA-N
in ch i: InChI=1S/C19H24N6O2/c1-13(27-15-8-6-14(7-9-15)19(2,3)4)16-10-11-20-18-23-17(24-25(16)18)21-12-22-26-5/h6-13H,1-5H3,(H,21,22,24)
comment: Potent KCa2.1 inhibitor
iupac name: N-{7-[1-(4-tert-butyl-phenoxy)ethyl]-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl}-N'-methoxy-formamidine
synonym: (-)-B-TPMF
approved: f
ligand name: B-TPMF
type: SyntheticOrganicLigand

CM-TPMF
canonical SMILES: CON=CNc1nn2c(n1)nccc2C(Oc1ccc(cc1C)Cl)C
isomeric SMILES: CON=CNc1nn2c(n1)nccc2C(Oc1ccc(cc1C)Cl)C
in ch i key: OZWWQEQUDKBSCF-UHFFFAOYSA-N
in ch i: InChI=1S/C16H17ClN6O2/c1-10-8-12(17)4-5-14(10)25-11(2)13-6-7-18-16-21-15(22-23(13)16)19-9-20-24-3/h4-9,11H,1-3H3,(H,19,20,22)
comment: Potent KCa2.1 activator
iupac name: N-{7-[1-(4-chloro-2-methylphenoxy)ethyl]-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl}-N'-methoxy-formamidine
synonym: (-)-CM-TPMF
approved: f
ligand name: CM-TPMF
type: SyntheticOrganicLigand

GW542573X
in ch i key: SAXGSDIZIYFNKD-UHFFFAOYSA-N
in ch i: InChI=1S/C19H28N2O5/c1-19(2,3)26-18(23)21-11-9-14(10-12-21)13-25-17(22)20-15-7-5-6-8-16(15)24-4/h5-8,14H,9-13H2,1-4H3,(H,20,22)
comment: Selective KCa2.1 channel activator
iupac name: tert-butyl 4-({[(2-methoxyphenyl)carbamoyl]oxy}methyl)piperidine-1-carboxylate
approved: f
ligand name: GW542573X
type: SyntheticOrganicLigand

SKA-20
canonical SMILES: Nc1nc2c(s1)c1cc3ccccc3cc1cc2
isomeric SMILES: Nc1nc2c(s1)c1cc3ccccc3cc1cc2
in ch i key: YKXKYTRQOWDNGL-UHFFFAOYSA-N
in ch i: InChI=1S/C15H10N2S/c16-15-17-13-6-5-11-7-9-3-1-2-4-10(9)8-12(11)14(13)18-15/h1-8H,(H2,16,17)
comment: Potent KCa2.1 activator
iupac name: anthra[2,1-d]thiazol-2-ylamine
approved: f
ligand name: SKA-20
type: SyntheticOrganicLigand

basimglurant
canonical SMILES: Fc1ccc(cc1)n1c(C)nc(c1C)C#Cc1ccnc(c1)Cl
isomeric SMILES: Fc1ccc(cc1)n1c(C)nc(c1C)C#Cc1ccnc(c1)Cl
in ch i key: UPZWINBEAHDTLA-UHFFFAOYSA-N
in ch i: InChI=1S/C18H13ClFN3/c1-12-17(8-3-14-9-10-21-18(19)11-14)22-13(2)23(12)16-6-4-15(20)5-7-16/h4-7,9-11H,1-2H3
comment: Basimglurant (RO4917523) is a negative allosteric modulator (NAM) of the glutamate metabotropic receptor 5 (mGlu5) GPCR <Reference id=31633/>, and is a clinical candidate in development for the treatment of psychiatric diseases. Structurally, basimglurant and <Ligand id=6409/> <Reference id=21789/> are analogues. CTEP has a notably longer half-life in rodents (49 hours) than basimglurant (~10 hours), so is better suited for rodent studies requiring chronic exposure/treatment.
iupac name: 2-chloro-4-[2-[1-(4-fluorophenyl)-2,5-dimethylimidazol-4-yl]ethynyl]pyridine
xref: CHEMBL3301626
synonym: RO-4917523
synonym: Ro4917523
synonym: RG-7090
synonym: compound 2 [PMID: 25565255]
approved: f
ligand name: basimglurant
type: SyntheticOrganicLigand

seltorexant
in ch i key: SQOCEMCKYDVLMM-UHFFFAOYSA-N
in ch i: InChI=1S/C21H22FN7O/c1-13-8-14(2)26-21(25-13)28-11-15-9-27(10-16(15)12-28)20(30)19-17(22)4-3-5-18(19)29-23-6-7-24-29/h3-8,15-16H,9-12H2,1-2H3
comment: Seltorexant (JNJ-42847922) is an investigational, selective OX2 receptor antagonist (2-SORA) <Reference id=31605/>. It is one of the compounds claimed in patent WO2011050198, where it is Example 107 <Reference id=31602/>. This compound is being developed jointly by Minerva Neurosciences and Janssen Pharmaceuticals for the treatment of major depression disorder and insomnia.
iupac name: [2-(4,6-dimethylpyrimidin-2-yl)-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrol-5-yl]-[2-fluoro-6-(triazol-2-yl)phenyl]methanone
synonym: JNJ-42847922
synonym: JNJ42847922
synonym: MIN-202
synonym: JNJ-922
approved: f
ligand name: seltorexant
type: SyntheticOrganicLigand

MK-3697
in ch i key: VSOUDUXMPUHJEU-UHFFFAOYSA-N
in ch i: InChI=1S/C23H21N5O3S/c1-14-8-15(11-24-10-14)19-9-17(18(13-26-19)23-25-6-7-32-23)21(29)27-12-16-4-5-20(30-2)22(28-16)31-3/h4-11,13H,12H2,1-3H3,(H,27,29)
comment: MK-3697 is a selective OX2 receptor antagonist (2-SORA) <Reference id=31600/>. 2-SORA class compounds are being investigated for potential clinical utility as treatments for insomnia.
iupac name: N-[(5,6-dimethoxypyridin-2-yl)methyl]-2-(5-methylpyridin-3-yl)-5-(1,3-thiazol-2-yl)pyridine-4-carboxamide
xref: CHEMBL3338865
synonym: compound 24 [PMID: 25248679]
approved: f
ligand name: MK-3697
type: SyntheticOrganicLigand

MK-1064
in ch i key: CKTWQGHVNRYNCM-UHFFFAOYSA-N
in ch i: InChI=1S/C24H20ClN5O3/c1-32-21-7-6-18(30-24(21)33-2)14-29-23(31)19-10-16(15-9-17(25)13-26-11-15)12-28-22(19)20-5-3-4-8-27-20/h3-13H,14H2,1-2H3,(H,29,31)
comment: MK-1064 is a selective OX2 receptor antagonist <Reference id=31597/><Reference id=31598/>. The acronym for selective OX2 receptor antagonists is 2-SORA (compared to DORA for dual OX1/OX2 antagonists).
iupac name: 5-(5-chloropyridin-3-yl)-N-[(5,6-dimethoxypyridin-2-yl)methyl]-2-pyridin-2-ylpyridine-3-carboxamide
xref: CHEMBL3338866
approved: f
ligand name: MK-1064
type: SyntheticOrganicLigand

Nag 26
in ch i key: RHLMXWCISNJNDH-UHFFFAOYSA-N
in ch i: InChI=1S/C32H34N4O5S/c1-22-8-5-10-25(18-22)31(37)34-17-16-33-27-12-7-13-28(21-27)35-42(39,40)30-20-24(14-15-29(30)41-4)23-9-6-11-26(19-23)32(38)36(2)3/h5-15,18-21,33,35H,16-17H2,1-4H3,(H,34,37)
comment: Compound 26 is a non-peptide, selective OX2 receptor agonist <Reference id=31596/>.
synonym: Nag26
synonym: compound 26 [PMID: 26267383]
approved: f
ligand name: Nag 26
type: SyntheticOrganicLigand

lemborexant
in ch i key: MUGXRYIUWFITCP-PGRDOPGGSA-N
in ch i: InChI=1S/C22H20F2N4O2/c1-13-19(11-25-14(2)27-13)30-12-22(15-4-3-5-16(23)8-15)9-18(22)21(29)28-20-7-6-17(24)10-26-20/h3-8,10-11,18H,9,12H2,1-2H3,(H,26,28,29)/t18-,22+/m0/s1
comment: Lemborexant (E2006) is an orally active, potent dual orexin receptor antagonist (DORA) <Reference id=31585/>.
iupac name: (1R,2S)-2-[(2,4-dimethylpyrimidin-5-yl)oxymethyl]-2-(3-fluorophenyl)-N-(5-fluoropyridin-2-yl)cyclopropane-1-carboxamide
xref: CHEMBL3545367
synonym: Dayvigo®
synonym: E2006
synonym: compound 34 [PMID: 25953512]
synonym: E-2006
approved: t
ligand name: lemborexant
type: SyntheticOrganicLigand

CHMFL-KIT-8140
in ch i key: QNWLWBMZIXFBPZ-UHFFFAOYSA-N
in ch i: InChI=1S/C34H36F3N5O5/c1-4-32(43)39-19-21-10-12-42(13-11-21)29-9-8-24(17-27(29)34(35,36)37)41-33(44)40-23-6-5-7-25(16-23)47-26-14-22-15-30(45-2)31(46-3)18-28(22)38-20-26/h5-9,14-18,20-21H,4,10-13,19H2,1-3H3,(H,39,43)(H2,40,41,44)
comment: CHMFL-KIT-8140 is a type II KIT inhibitor capable of inhibiting the wild type kinase and theT670I gatekeeper mutant <Reference id=31569/>. KIT is a Tec family receptor tyrosine kinase.
iupac name: N-[(1-{4-[({3-[(6,7-dimethoxyquinolin-3-yl)oxy]phenyl}carbamoyl)amino]-2-(trifluoromethyl)phenyl}piperidin-4-yl)methyl]propanamide
approved: f
ligand name: CHMFL-KIT-8140
type: SyntheticOrganicLigand

compound 5a [PMID: 27536893]
in ch i key: FFKCRLSRMMVTAN-UHFFFAOYSA-N
in ch i: InChI=1S/C21H19N5O4/c1-3-30-13-10-8-12(9-11-13)19-23-16(18(22)27)17-20(25-19)26(21(28)24-17)14-6-4-5-7-15(14)29-2/h4-11H,3H2,1-2H3,(H2,22,27)(H,24,28)
comment: Compound 5a causes microtubule fragmentation via modulation of the hydrolase activity of katanin <Reference id=31568/>. The precise binding site has not been determined, but could reside within catalytic site of KATNA1 (p60 subunit) due to the purine scaffold of 5a. A docking model suggests that 5a may bind in a position which stabilizes the p60 structure and enhances the microtubule severing activity of katanin. Katanin-modulating compounds could provide an alternative to vinca alkaloid and taxane microtubule targeting agents (MTAs), which suffer from issues of drug-induced resistance developing in clinical use.
iupac name: 2-(4-ethoxyphenyl)-9-(2-methoxyphenyl)-8-oxo-7H-purine-6-carboxamide
approved: f
ligand name: compound 5a [PMID: 27536893]
type: SyntheticOrganicLigand

fenebrutinib
in ch i key: WNEODWDFDXWOLU-QHCPKHFHSA-N
in ch i: InChI=1S/C37H44N8O4/c1-23-18-42(27-21-49-22-27)9-10-43(23)26-5-6-33(39-17-26)40-30-13-25(19-41(4)35(30)47)28-7-8-38-34(29(28)20-46)45-12-11-44-31(36(45)48)14-24-15-37(2,3)16-32(24)44/h5-8,13-14,17,19,23,27,46H,9-12,15-16,18,20-22H2,1-4H3,(H,39,40)/t23-/m0/s1
comment: Fenebrutinib (RG7845, GDC-0853) is a Bruton's tyrosine kinase (BTK) inhibitor, under investigation for therapeutic potential in difficult-to-treat autoimmune diseases. The compound is claimed in patent WO2013067274 <Reference id=31565/>.
iupac name: (S)-2-(3'-(hydroxymethyl)-1-methyl-5-((5-(2-methyl-4-(oxetan-3-yl)piperazin-1-yl)pyridin-2-yl)amino)-6-oxo-1,6-dihydro-[3,4'-bipyridin]-2'-yl)-7,7-dimethyl-3,4,7,8-tetrahydro-2H-cyclopenta[4,5]pyrrolo[1,2-a]pyrazin-1(6H)-one
synonym: RG7845
synonym: GDC-0853
synonym: Example 130 [US20140194408]
synonym: RG-7845
synonym: GDC0853
synonym: GDC 0853
synonym: RG 7845
approved: f
ligand name: fenebrutinib
type: SyntheticOrganicLigand

CGI560
in ch i key: IJMHHZDBRUGXNO-UHFFFAOYSA-N
in ch i: InChI=1S/C29H27N5O/c1-29(2,3)22-14-12-20(13-15-22)28(35)32-24-11-7-8-21(18-24)25-19-34-17-16-30-27(34)26(33-25)31-23-9-5-4-6-10-23/h4-19H,1-3H3,(H,31,33)(H,32,35)
comment: CGI560 is a potent, reversible Bruton's tyrosine kinase (BTK) inhibitor, that was tested preclinically for potential clinical utility in inflammatory diseases and B cell malignancies. Structure depicted in <Reference id=26634/>. Hit-to-lead chemistry based on CGI560's structure resulted in the discovery of <Ligand id=8066/>, with improved potency and selectivity <Reference id=26634/>.
xref: CHEMBL2057914
synonym: CGI-560
approved: f
ligand name: CGI560
type: SyntheticOrganicLigand

LHVS
in ch i key: YUMYYTORLYHUFW-ZUDLOMHPSA-N
in ch i: InChI=1S/C28H37N3O5S/c1-22(2)21-26(30-28(33)31-16-18-36-19-17-31)27(32)29-24(14-13-23-9-5-3-6-10-23)15-20-37(34,35)25-11-7-4-8-12-25/h3-12,15,20,22,24,26H,13-14,16-19,21H2,1-2H3,(H,29,32)(H,30,33)/b20-15+/t24-,26-/m1/s1
comment: LHVS is a small molecule, vinyl sulfone type, tool compound, which inhibits cathepsins L and S with low nanomolar potency <Reference id=31562/>. Cathepsin S inhibitors are being investigated for clinical utility in inflammatory conditions. LHVS is reported to have neuroprotective action in models of traumatic brain injury <Reference id=31563/>.
iupac name: N-[(2R)-4-methyl-1-oxo-1-[[(E,3R)-5-phenyl-1-phenylsulfonylpent-1-en-3-yl]amino]pentan-2-yl]morpholine-4-carboxamide
xref: CHEMBL222649
synonym: morpholinurea-leucine-homophenylalaninevinyl phenyl sulfone
synonym: morpholinurea-leucine-homophenylalanine-vinylsulfone-phenyl
approved: f
ligand name: LHVS
type: SyntheticOrganicLigand

BU08028
in ch i key: HBENZIXOGRCSQN-VQWWACLZSA-N
in ch i: InChI=1S/C30H43NO4/c1-6-26(2,3)27(4,33)21-16-28-11-12-30(21,34-5)25-29(28)13-14-31(17-18-7-8-18)22(28)15-19-9-10-20(32)24(35-25)23(19)29/h9-10,18,21-22,25,32-33H,6-8,11-17H2,1-5H3/t21-,22-,25-,27+,28-,29+,30-/m1/s1
comment: BU08028 is a novel research compound that provides the pain relief of opiates, without their addictive effects in mouse models of acute pain and cocaine-induced reward <Reference id=31549/><Reference id=31550/>. Structurally it is a derivative of <Ligand id=1670/>, with only the addition of an additional methylene group at the C20 substituent. Increasing affinity for the NOP receptor is predicted to reduce the behavioural side-effects associated with buprenorphine. Note that the compound referred to as 1b in <Reference id=31550/> has a marginally different stereo compared to the same compound (named as BUB8028) in <Reference id=31549/>, with identical data provided for 1b and BUB8028 in both articles. Compound 1b resolves to PubChem CID 56664973. We have chosen to link to CID 50922685 as the specified stereochemistry of this is identical to that of buprenorphine.
iupac name: (2S)-2-[(5R,6R,7R,14S)-N-cyclopropylmethyl-4,5-epoxy-6,14-ethano-3-hydroxy-6-methoxymorphinan-7-yl]-3,3-dimethylpentan-2-ol
synonym: compound 1b [PMID: 21866885]
approved: f
ligand name: BU08028
type: SyntheticOrganicLigand

siponimod
isomeric SMILES: CCc1cc(ccc1CN1CC(C1)C(=O)O)/C(=N/OCc1ccc(c(c1)C(F)(F)F)C1CCCCC1)/C
in ch i key: KIHYPELVXPAIDH-HNSNBQBZSA-N
in ch i: InChI=1S/C29H35F3N2O3/c1-3-21-14-23(10-11-24(21)15-34-16-25(17-34)28(35)36)19(2)33-37-18-20-9-12-26(22-7-5-4-6-8-22)27(13-20)29(30,31)32/h9-14,22,25H,3-8,15-18H2,1-2H3,(H,35,36)/b33-19+
comment: Pharmacologically, siponimod (BAF312) is a selective sphingosine-1-phosphate (S1P) receptor agonist, with some selectivity for the S1P1 and S1P5 receptor isoforms <Reference id=31524/>. It is an orally active drug. Siponimod was developed by Novartis for secondary progressive multiple sclerosis (SPMS), originally as a back-up compound for <Ligand id=2407/>. Compared to fingolimod it has more favourable pharmacokinetics. Novartis announced positive results from their Phase 3 EXPAND study (BAF312 versus placebo) in SPMS (August 2016- link to announcement here). The SIPR signalling pathway is important in autoimmune biology.
iupac name: 1-[[4-[(E)-N-[[4-cyclohexyl-3-(trifluoromethyl)phenyl]methoxy]-C-methylcarbonimidoyl]-2-ethylphenyl]methyl]azetidine-3-carboxylic acid
xref: CHEMBL2336071
synonym: Mayzent®
synonym: BAF312
synonym: BAF-312
synonym: compound 32 [PMID: 24900670]
approved: t
ligand name: siponimod
type: SyntheticOrganicLigand

abiraterone acetate
in ch i key: UVIQSJCZCSLXRZ-UBUQANBQSA-N
in ch i: InChI=1S/C26H33NO2/c1-17(28)29-20-10-12-25(2)19(15-20)6-7-21-23-9-8-22(18-5-4-14-27-16-18)26(23,3)13-11-24(21)25/h4-6,8,14,16,20-21,23-24H,7,9-13,15H2,1-3H3/t20-,21-,23-,24-,25-,26+/m0/s1
comment: Abiraterone acetate is an ester prodrug of the steroidal drug abiraterone, which acts as an androgen synthesis inhibitor by inhibiting steroid 17alpha-monooxygenase.
iupac name: [(3S,8R,9S,10R,13S,14S)-10,13-dimethyl-17-pyridin-3-yl-2,3,4,7,8,9,11,12,14,15-decahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate
xref: CHEMBL271227
synonym: Yonsa®
synonym: Zytiga®
approved: t
ligand name: abiraterone acetate
type: SyntheticOrganicLigand

dextrorphan
canonical SMILES: Oc1ccc2c(c1)C13CCCCC3C(C2)N(CC1)C
in ch i key: JAQUASYNZVUNQP-PVAVHDDUSA-N
in ch i: InChI=1S/C17H23NO/c1-18-9-8-17-7-3-2-4-14(17)16(18)10-12-5-6-13(19)11-15(12)17/h5-6,11,14,16,19H,2-4,7-10H2,1H3/t14-,16+,17+/m1/s1
comment: Dextrorphan is an NMDA receptor antagonist. It is the dextro-rotatory isomer of <Ligand id=7595/> and is also an active metabolite of <Ligand id=6953/>.
xref: CHEMBL1254766
approved: f
ligand name: dextrorphan
type: SyntheticOrganicLigand

GSK1521498
in ch i key: WIEDUMBCZQRGSY-UHFFFAOYSA-N
in ch i: InChI=1S/C24H20F2N4/c25-22-11-19(15-6-3-7-18(8-15)24-28-14-29-30-24)12-23(26)21(22)13-27-20-9-16-4-1-2-5-17(16)10-20/h1-8,11-12,14,20,27H,9-10,13H2,(H,28,29,30)
comment: GSK1521498 is a μ opioid receptor antagonist <Reference id=31515/><Reference id=31516/> in clinical development for disorders of compulsive consumption (e.g stimulant drug seeking, binge eating <Reference id=31513/>, or excessive alcohol consumption). It is >10-fold selective for human μ receptor compared to the κ and δ receptors in vitro <Reference id=31516/>. It may be used experimentally as the phosphate with IUPAC name N-{[3,5-difluoro-3′-(1H-1,2,4-triazol-3-yl)-4-biphenylyl]methyl}-2,3-dihydro-1H-inden-2-amine phosphate (1:1). The chemical structure of GSK1521498 is claimed in patent US8822518 <Reference id=31517/>, with prior chemical series claimed in WO2008021849 <Reference id=31518/>.
synonym: GSK-1521498
synonym: GSK 1521498
approved: f
ligand name: GSK1521498
type: SyntheticOrganicLigand

PZM21
in ch i key: MEDBIJOVZJEMBI-YOEHRIQHSA-N
in ch i: InChI=1S/C19H27N3O2S/c1-14(10-16-8-9-25-13-16)21-19(24)20-12-17(22(2)3)11-15-4-6-18(23)7-5-15/h4-9,13-14,17,23H,10-12H2,1-3H3,(H2,20,21,24)/t14-,17-/m0/s1
comment: PZM21 is a potent, selective μ opioid receptor agonist with bias towards G-protein (Gi) activation over β-arrestin 2 recruitment <Reference id=31499/>. This provides a compound with reduced propensity to produce common opioid side effects whilst retaining analgesic activity. PZM21 is being used experimentally for its analgesic activity. This compound is not in PubChem and its SMILES string does not retrieve any patent documents from SureChembl (late August 2016). Compare this with <Ligand id=7334/>, a chemically unrelated μ opioid receptor G-protein biased agonist.
iupac name: 1-[(2S)-2-(dimethylamino)-3-(4-hydroxyphenyl)propyl]-3-[(2S)-1-(thiophen-3-yl)propan-2-yl]urea
synonym: (S,S)-21 [PMID: 27533032]
synonym: (S,S)-1-[2-(dimethylamino)-3-(4-hydroxyphenyl)propyl]-3-(1-thiophen-3-ylpropan-2-yl)urea
approved: f
ligand name: PZM21
type: SyntheticOrganicLigand

PRN694
in ch i key: NXTKFBGDLDPFLB-PKOBYXMFSA-N
comment: PRN694 is a small molecule, covalent inhibitor somewhat selective for the TEC family kinases, IL-2-inducible T cell kinase (ITK) and TXK tyrosine kinase (also known as resting lymphocyte kinase or RLK) <Reference id=31478/><Reference id=31477/>. In vitro PRN694 is a potent inhibitor of Th1 and Th17 differentiation and cytokine production (IFN-γ production for Th1 and IL-17A for Th17), and in vivo PRN694 markedly reduces disease progression in a mouse colitis model <Reference id=31477/>. It is suggested that dual ITK and RLK inhibition may represent a novel therapeutic model for amelioration of Th1-mediated inflammatory diseases. Mechanistically PRN694 inhibits kinase activity by binding irreversibly to cysteine residue 442 of ITK and 350 of RLK <Reference id=31478/>. A series of compounds including PRN694 is claimed in patent WO2014036016 <Reference id=31479/>. Example 29 is an enantiomer of PRN694 with one unspecified stereocenter.
iupac name: 5-(difluoromethyl)-N-[5-[[[(2S)-3,3-dimethylbutan-2-yl]amino]methyl]-1-[[(2R)-1-prop-2-enoylpyrrolidin-2-yl]methyl]benzimidazol-2-yl]thiophene-2-carboxamide
approved: f
ligand name: PRN694
type: SyntheticOrganicLigand

TP508
in ch i key: MOZAQZCGIKWACU-VKDININFSA-N
comment: TP508 is a synthetic 23 amino acid peptide corresponding to amino acids 183 to 205 of the endogenous wound healing molecule human thrombin <Reference id=31473/>. TP508 has been investigated as an activator of soft and hard tissue repair <Reference id=31467/><Reference id=31470/><Reference id=31471/><Reference id=31474/><Reference id=31475/>, and for its potential to mitigate tissue damage caused by radiation exposure <Reference id=31468/><Reference id=31469/>. TP508 may also provide an alternative to stem cell therapy in regenerative medicine.
synonym: Chrysalin
approved: f
ligand name: TP508
type: PeptideLigand

TG6-129
in ch i key: SYSMVOANBVDZNG-LFYBBSHMSA-N
comment: TG6-129 is a selective prostanoid EP2 receptor antagonist probe <Reference id=31449/>. As it does not the blood brain barrier it is a useful tool for investigating peripheral anti-inflammatory mechanisms of EP2 antagonism. Peripherally acting EP2 antagonists are being investigated for clinical potential in chronic inflammatory diseases such as rheumatoid arthritis and chronic obstructive pulmonary disease (COPD).
xref: CHEMBL1372836
approved: f
ligand name: TG6-129
type: SyntheticOrganicLigand

U-47700
canonical SMILES: CN(C1CCCCC1N(C(=O)c1ccc(c(c1)Cl)Cl)C)C
in ch i key: JGPNMZWFVRQNGU-HUUCEWRRSA-N
in ch i: InChI=1S/C16H22Cl2N2O/c1-19(2)14-6-4-5-7-15(14)20(3)16(21)11-8-9-12(17)13(18)10-11/h8-10,14-15H,4-7H2,1-3H3/t14-,15-/m1/s1
comment: U-47700 is a selective μ-opioid receptor agonist <Reference id=31437/>, with in vivo effects similar to other potent opioid agonists (analgesia, sedation, euphoria, constipation and respiratory depression). Illicit use and fatalities caused by U-47700 <Reference id=31438/><Reference id=31439/><Reference id=31440/> has prompted action to schedule the compound or make it illegal in some jurisdictions.
iupac name: 3,4-dichloro-N-[(1R,2R)-2-(dimethylamino)cyclohexyl]-N-methylbenzamide
xref: CHEMBL277572
synonym: compound 1 [PMID: 2999404]
approved: f
ligand name: U-47700
type: SyntheticOrganicLigand

serlopitant
in ch i key: FLNYCRJBCNNHRH-OIYLJQICSA-N
in ch i: InChI=1S/C29H28F7NO2/c1-16(19-10-20(28(31,32)33)12-21(11-19)29(34,35)36)39-26-9-4-18-14-37(23-7-8-24(38)13-23)15-25(18)27(26)17-2-5-22(30)6-3-17/h2-3,5-6,10-13,16,18,25-27H,4,7-9,14-15H2,1H3/t16-,18-,25-,26+,27+/m1/s1
comment: Serlopitant is a potent, brain-penetrant neurokinin (NK1) receptor antagonist <Reference id=31426/>, being investigated for antiinflammatory action. It has more favourable pharmacology than the approved NK1 antagonist <Ligand id=3490/>.
iupac name: 3-[(3aR,4R,5S,7aS)-5-[(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethoxy]-4-(4-fluorophenyl)-1,3,3a,4,5,6,7,7a-octahydroisoindol-2-yl]cyclopent-2-en-1-one
xref: CHEMBL447955
synonym: VPD-737
synonym: compound 17 (Jiang et al. 2009)
approved: f
ligand name: serlopitant
type: SyntheticOrganicLigand

asimadoline
in ch i key: JHLHNYVMZCADTC-LOSJGSFVSA-N
in ch i: InChI=1S/C27H30N2O2/c1-28(25(21-11-5-2-6-12-21)20-29-18-17-24(30)19-29)27(31)26(22-13-7-3-8-14-22)23-15-9-4-10-16-23/h2-16,24-26,30H,17-20H2,1H3/t24-,25+/m0/s1
comment: Asimadoline is an orally active, selective kappa-opioid receptor agonist. It exhibits little blood-brain barrier penetrance so is considered peripherally acting. Asimadoline has demonstrated efficacy in several preclinical pruritus models, and has been investigated as a therapy for irritable bowel syndrome.
iupac name: N-[(1S)-2-[(3S)-3-hydroxypyrrolidin-1-yl]-1-phenylethyl]-N-methyl-2,2-di(phenyl)acetamide
xref: CHEMBL1190199
synonym: EMD-61753
synonym: EMD 61753
synonym: EMD 61 753
approved: f
ligand name: asimadoline
type: SyntheticOrganicLigand

compound 4g [PMID: 2680437]
canonical SMILES: O=c1oc2c(n1Cc1nnn(c1)c1ccccc1Cl)nccc2
isomeric SMILES: O=c1oc2c(n1Cc1nnn(c1)c1ccccc1Cl)nccc2
in ch i key: DVUFHXDFLFFOFE-UHFFFAOYSA-N
in ch i: InChI=1S/C15H10ClN5O2/c16-11-4-1-2-5-12(11)21-9-10(18-19-21)8-20-14-13(23-15(20)22)6-3-7-17-14/h1-7,9H,8H2
comment: Compound 4g is a GSK-3β inhibitor with anti-inflammatory activity <Reference id=31043/>.
iupac name: 3-{[1-(2-chlorophenyl)-1H-1,2,3-triazol-4-yl]methyl}-2H,3H-[1,3]oxazolo[4,5-b]pyridin-2-one
approved: f
ligand name: compound 4g [PMID: 2680437]
type: SyntheticOrganicLigand

tradipitant
in ch i key: CAVRKWRKTNINFF-UHFFFAOYSA-N
comment: Tradipitant is an orally available antagonist of the NK1 subtype of tachykinin receptors. It is Example 132 claimed in patent WO2003091226 <Reference id=31422/>. Tradipitant is being investigated for potential anti-pruritic action in patients with atopic dermatitis.
iupac name: [2-[1-[[3,5-bis(trifluoromethyl)phenyl]methyl]-5-pyridin-4-yltriazol-4-yl]pyridin-3-yl]-(2-chlorophenyl)methanone
synonym: VLY-686
synonym: LY-686017
synonym: LY686017
approved: f
ligand name: tradipitant
type: SyntheticOrganicLigand

timapiprant
in ch i key: FATGTHLOZSXOBC-UHFFFAOYSA-N
in ch i: InChI=1S/C21H17FN2O2/c1-13-17(11-16-8-6-14-4-2-3-5-19(14)23-16)18-10-15(22)7-9-20(18)24(13)12-21(25)26/h2-10H,11-12H2,1H3,(H,25,26)
comment: Timapiprant (OC000459) is a potent, selective, and orally active DP2 receptor antagonist <Reference id=31421/><Reference id=31466/>.
iupac name: 2-[5-fluoro-2-methyl-3-(quinolin-2-ylmethyl)indol-1-yl]acetic acid
xref: CHEMBL560993
synonym: OC000459
synonym: OC459
approved: f
ligand name: timapiprant
type: SyntheticOrganicLigand

toreforant
in ch i key: FCRFVPZAXGJLPW-UHFFFAOYSA-N
in ch i: InChI=1S/C23H32N6/c1-15-12-16(2)21-20(13-15)27-22(28-21)19-14-25-23(26-17(19)3)24-9-5-6-18-7-10-29(4)11-8-18/h12-14,18H,5-11H2,1-4H3,(H,27,28)(H,24,25,26)
comment: Toreforant is a selective histamine H4 receptor antagonist claimed as Example 7 in patent WO2007117399 <Reference id=31419/>. It is being investigated for its potential antiinflammarory action in allergy, asthma, autoimmune diseases, and pruritis.
iupac name: 5-(4,6-dimethyl-1H-benzimidazol-2-yl)-4-methyl-N-[3-(1-methylpiperidin-4-yl)propyl]pyrimidin-2-amine
xref: CHEMBL3301609
synonym: JNJ-38518168
approved: f
ligand name: toreforant
type: SyntheticOrganicLigand

leucomethylthioninium
canonical SMILES: C[NH+](c1ccc2c(c1)Sc1c(N2)ccc(c1)[NH+](C)C)C
isomeric SMILES: C[NH+](c1ccc2c(c1)Sc1c(N2)ccc(c1)[NH+](C)C)C
in ch i key: QTWZICCBKBYHDM-UHFFFAOYSA-P
in ch i: InChI=1S/C16H19N3S/c1-18(2)11-5-7-13-15(9-11)20-16-10-12(19(3)4)6-8-14(16)17-13/h5-10,17H,1-4H3/p+2
comment: Leucomethylthioninium complexed with bromide or methane sulfonate (LMTX) was designed as a methylthioninium chloride (MTC, or methylene blue) analogue with improved pharmacokinetic properties <Reference id=31405/>. MTC and LMTX are tau aggregation inhibitors with potential in Alzheimer's disease (AD) and other tau-opathies. We believe this is the compound being investigated in Phase 3 clinical trials as TRx0237.
iupac name: N3,N3,N7,N7-tetramethyl-10H-phenothiazine-3,7-bis(aminium)
synonym: leuco-methylthioninium
synonym: TRx0237
synonym: TRx-0237
synonym: LMTX
synonym: LMTM
approved: f
ligand name: leucomethylthioninium
type: SyntheticOrganicLigand

EPZ011989
in ch i key: XQFINGFCBFHOPE-UHFFFAOYSA-N
in ch i: InChI=1S/C35H51N5O4/c1-7-40(30-12-10-29(11-13-30)38(5)15-18-43-6)33-23-28(9-8-14-39-16-19-44-20-17-39)22-31(27(33)4)34(41)36-24-32-25(2)21-26(3)37-35(32)42/h21-23,29-30H,7,10-20,24H2,1-6H3,(H,36,41)(H,37,42)
comment: EPZ011989 is a 3nM selective, orally bioavailable inhibitor of EZH2 with tumor growth inhibition in a mouse xenograft model of human B cell lymphoma <Reference id=31300/>. It has a Probe Portal entry SGC EPZ011989.
approved: f
ligand name: EPZ011989
type: SyntheticOrganicLigand

setmelanotide
in ch i key: HDHDTKMUACZDAA-PHNIDTBTSA-N
comment: Setmelanotide is an agonist of melanocortin receptors, with approximately 20-fold selectivity for the melanocortin 4 receptor subtype <Reference id=31400/>. Chemically it is an eight-amino-acid cyclic peptide, that is able to cross the blood-brain barrier when administered peripherally. Setmelanotide offers anti-obesity potential. The INN record documents the sequence as N2-acetyl-L-arginyl-L-cysteinyl-D-alanyl-L-histidyl-D-phenylalanyl-L-arginyl-L-tryptophyl-L-cysteinamide, cyclic (2-8)-disulfide.
synonym: RM-493
synonym: BIM-22493
synonym: IRC-022493
synonym: Imcivree®
approved: t
ligand name: setmelanotide
type: PeptideLigand

MPS1-IN-1
in ch i key: NMJMRSQTDLRCRQ-UHFFFAOYSA-N
in ch i: InChI=1S/C28H33N5O4S/c1-18(2)38(35,36)26-7-5-4-6-23(26)30-24-17-27(32-28-21(24)10-13-29-28)31-22-9-8-19(16-25(22)37-3)33-14-11-20(34)12-15-33/h4-10,13,16-18,20,34H,11-12,14-15H2,1-3H3,(H3,29,30,31,32)
comment: Mps1, a dual-specificity kinase, is required for the proper functioning of the spindle assembly checkpoint and for the maintenance of chromosomal stability. MPS1-IN-1 leads to defects in Mad1 and Mad2 establishment at unattached kinetochores, decreased Aurora B kinase activity, premature mitotic exit and gross aneuploidy. In addtion inhibitor treatment resulted in a decrease in cancer cell viability <Reference id=19817/>. While this is included in the Probe Portal as SGC MPS1-IN-1, it is superceded by more potent and specific compounds.
iupac name: 1-[3-methoxy-4-[[4-(2-propan-2-ylsulfonylanilino)-1H-pyrrolo[2,3-b]pyridin-6-yl]amino]phenyl]piperidin-4-ol
approved: f
ligand name: MPS1-IN-1
type: SyntheticOrganicLigand

3M-002
canonical SMILES: CCCc1nc2c(s1)c1ccccc1nc2N
isomeric SMILES: CCCc1nc2c(s1)c1ccccc1nc2N
in ch i key: NFYMGJSUKCDVJR-UHFFFAOYSA-N
in ch i: InChI=1S/C13H13N3S/c1-2-5-10-16-11-12(17-10)8-6-3-4-7-9(8)15-13(11)14/h3-4,6-7H,2,5H2,1H3,(H2,14,15)
comment: 3M-002 is reported as a selective Toll-like receptor 8 agonist, which promotes TNF-α and IL-12 production from human PBMCs <Reference id=31396/>.
iupac name: 2-propyl-[1,3]thiazolo[4,5-c]quinolin-4-amine
xref: CHEMBL512901
synonym: CL-075
synonym: CL075
approved: f
ligand name: 3M-002
type: SyntheticOrganicLigand

BMX-IN-1
in ch i key: SFMJNHNUOVADRW-UHFFFAOYSA-N
in ch i: InChI=1S/C29H24N4O4S/c1-4-27(34)31-26-16-23(12-5-18(26)2)33-28(35)14-9-21-17-30-25-13-8-20(15-24(25)29(21)33)19-6-10-22(11-7-19)32-38(3,36)37/h4-17,32H,1H2,2-3H3,(H,31,34)
comment: BMX-IN-1 is a selective and irreversible inhibitor (8nM IC50) which covalently modifies Cys496 in the BMX kinase and exhibits antiproliferation efficacy against prostate cancer cells <Reference id=31297/>. This compound has a Probe Portal entry SGC BMX-IN-1. A series of analogues of this structure with activity data are disclosed in a 2014 patent <Reference id=31398/>
iupac name: N-[5-[9-[4-(methanesulfonamido)phenyl]-2-oxobenzo[h][1,6]naphthyridin-1-yl]-2-methylphenyl]prop-2-enamide
synonym: Example 1-14 [ WO2014063054]
approved: f
ligand name: BMX-IN-1
type: SyntheticOrganicLigand

compound 4g [PMID: 22220592]
canonical SMILES: Nc1nnc(c(n1)c1ccccc1)c1cc(C)nc(c1)C
isomeric SMILES: Nc1nnc(c(n1)c1ccccc1)c1cc(C)nc(c1)C
in ch i key: SORFNYWLKDSNNF-UHFFFAOYSA-N
in ch i: InChI=1S/C16H15N5/c1-10-8-13(9-11(2)18-10)15-14(19-16(17)21-20-15)12-6-4-3-5-7-12/h3-9H,1-2H3,(H2,17,19,21)
comment: Compound 4g [PMID: 22220592]) is a potent, efficient, selective, and orally active 1,2,4-triazine derivative ligand. Heptares identified this compound using structure-based drug design approaches to discover antagonists of the adenosine A2A receptor <Reference id=36719/><Reference id=31293/>. The X-ray crystal structure of 4g locates it inside the receptor's orthosteric binding cavity <Reference id=25366/>.
iupac name: 6-(2,6-dimethylpyridin-4-yl)-5-phenyl-1,2,4-triazin-3-amine
xref: CHEMBL2024115
synonym: Example XCII [US20160175314]
approved: f
ligand name: compound 4g [PMID: 22220592]
type: SyntheticOrganicLigand

AZ191
in ch i key: ZYVXTMKTGDARKR-UHFFFAOYSA-N
in ch i: InChI=1S/C24H27N7O/c1-29-10-12-31(13-11-29)17-4-5-21(23(14-17)32-3)28-24-26-9-7-20(27-24)19-16-30(2)22-15-25-8-6-18(19)22/h4-9,14-16H,10-13H2,1-3H3,(H,26,27,28)
comment: AZ191 is a potent and selective small molecule inhibitor of DYRK1B from AstraZeneca <Reference id=31298/>. Results of a 2014 study <Reference id=31299/> using AZ191 indicate DYRK1B is a novel Thr(286)-CCND1(cyclinD1) kinase that acts independently of GSK3β to regulate the mammalian G1-S-phase transition. This compound is included in the Probe Portal as SGC AZ191. It was tested in preclinical studies.
iupac name: N-[2-methoxy-4-(4-methylpiperazin-1-yl)phenyl]-4-(1-methylpyrrolo[2,3-c]pyridin-3-yl)pyrimidin-2-amine
xref: CHEMBL3421968
synonym: Compound 19 [PMID25738750]
synonym: AZ-191
approved: f
ligand name: AZ191
type: SyntheticOrganicLigand

dihydrexidine
canonical SMILES: Oc1cc2CCC3C(c2cc1O)c1ccccc1CN3
isomeric SMILES: Oc1cc2CC[C@H]3[C@H](c2cc1O)c1ccccc1CN3
in ch i key: BGOQGUHWXBGXJW-YOEHRIQHSA-N
in ch i: InChI=1S/C17H17NO2/c19-15-7-10-5-6-14-17(13(10)8-16(15)20)12-4-2-1-3-11(12)9-18-14/h1-4,7-8,14,17-20H,5-6,9H2/t14-,17-/m0/s1
comment: Dihydrexidine is a moderately selective full agonist at the dopamine D1 and D5 receptors. Currently undergoing clinical trials to assess its efficacy in improving the cognitive and working memory deficits in schizophrenia and schizotypal disorder. Results of a proof-of-principle study are reported in <Reference id=31395/>.
iupac name: (6aS,12bR)-5,6,6a,7,8,12b-hexahydrobenzo[a]phenanthridine-10,11-diol
synonym: DAR 0100A
synonym: DAR-0100A
synonym: DAR0100A
approved: f
ligand name: dihydrexidine
type: SyntheticOrganicLigand

CNX-774
in ch i key: VVLHQJDAUIPZFH-UHFFFAOYSA-N
in ch i: InChI=1S/C26H22FN7O3/c1-3-23(35)31-17-5-4-6-18(13-17)32-24-21(27)15-30-26(34-24)33-16-7-9-19(10-8-16)37-20-11-12-29-22(14-20)25(36)28-2/h3-15H,1H2,2H3,(H,28,36)(H,31,35)(H2,30,32,33,34)
comment: CNX-774 is a selective, orally available and irreversible (covalent) Bruton's tyrosine kinase (BTK) inhibitor, tested preclinically for autoimmune diseases, and B-cell non-Hodgkin's lymphoma. Its chemical structure is shown in <Reference id=24420/>. CNX-774 forms a covalent bond with Cys481 within the active site of the enzyme.
iupac name: 4-[4-[[5-fluoro-4-[3-(prop-2-enoylamino)anilino]pyrimidin-2-yl]amino]phenoxy]-N-methylpyridine-2-carboxamide
xref: CHEMBL2216827
approved: f
ligand name: CNX-774
type: SyntheticOrganicLigand

tirabrutinib
in ch i key: SEJLPXCPMNSRAM-GOSISDBHSA-N
in ch i: InChI=1S/C25H22N6O3/c1-2-6-21(32)29-14-13-18(15-29)31-24-22(23(26)27-16-28-24)30(25(31)33)17-9-11-20(12-10-17)34-19-7-4-3-5-8-19/h3-5,7-12,16,18H,13-15H2,1H3,(H2,26,27,28)/t18-/m1/s1
comment: Tirabrutinib (ONO-4059) is a potent, reversible Bruton's tyrosine kinase (BTK) inhibitor. It is one of the compounds claimed in patent WO2013081016A1, where Example 9 is tirabrutinib hydrochloride <Reference id=42456/>.
iupac name: 6-amino-9-[(3R)-1-but-2-ynoylpyrrolidin-3-yl]-7-(4-phenoxyphenyl)purin-8-one
xref: CHEMBL4071161
synonym: ONO-4059
synonym: GS-4059
synonym: ONO4059
synonym: Velexbru®
approved: t
ligand name: tirabrutinib
type: SyntheticOrganicLigand

GDC-0834
in ch i key: CDOOFZZILLRUQH-GDLZYMKVSA-N
in ch i: InChI=1S/C33H36N6O3S/c1-20-24(9-7-10-25(20)36-31(40)28-18-22-8-5-6-11-27(22)43-28)26-19-39(4)33(42)30(35-26)34-23-14-12-21(13-15-23)29-32(41)38(3)17-16-37(29)2/h7,9-10,12-15,18-19,29H,5-6,8,11,16-17H2,1-4H3,(H,34,35)(H,36,40)/t29-/m1/s1
comment: GDC-0834 was identified as a clinical candidate antiinflammatory Bruton's tyrosine kinase (BTK) inhibitor, through SAR guided improvements to the pharmacokinetic (PK) properties of the potent and selective BTK inhibitor <Ligand id=8066/> <Reference id=31366/>. GDC-0834 retains CGI1746's selectivity but exhibits significantly improved PK in preclinical animal models <Reference id=31369/>. Studies suggest the involvement of aldehyde oxidase (AO) in the rapid amide hydrolysis of GDC-0834 to an inactive metabolite <Reference id=31367/>, which severly impacted on its ability to sustain beneficial clinical effects. Significant species difference in AO-induced inactivation of GDC-0834 are reported and explain why this was not picked up during preclinical studies <Reference id=31368/>. Clinical development was terminated, with the manufacturer using insight gained to inform their search for improved inhibitors.
iupac name: N-[3-[6-[4-[(2R)-1,4-dimethyl-3-oxopiperazin-2-yl]anilino]-4-methyl-5-oxopyrazin-2-yl]-2-methylphenyl]-4,5,6,7-tetrahydro-1-benzothiophene-2-carboxamide
xref: CHEMBL2057915
synonym: GDC0834
synonym: GDC 0834
approved: f
ligand name: GDC-0834
type: SyntheticOrganicLigand

LFM-A13
canonical SMILES: CC(=C(C(=O)Nc1cc(Br)ccc1Br)C#N)O
isomeric SMILES: C/C(=C(/C(=O)Nc1cc(Br)ccc1Br)/C#N)/O
in ch i key: UVSVTDVJQAJIFG-VURMDHGXSA-N
in ch i: InChI=1S/C11H8Br2N2O2/c1-6(16)8(5-14)11(17)15-10-4-7(12)2-3-9(10)13/h2-4,16H,1H3,(H,15,17)/b8-6-
comment: LFM-A13 is a potent, cell-permeable, reversible, substrate competitive, and specific inhibitor of Bruton's tyrosine kinase (BTK) <Reference id=31360/>. It was the first reported BTK-selective tyrosine kinase inhibitor and the first anti-leukemic agent targeting BTK. Investigated preclinically for B-cell non-Hodgkin's lymphoma <Reference id=31362/><Reference id=31361/>. Structurally LFM-A13 is an analogue of a metabolite of the antirheumatic drug <Ligand id=6825/>. The Mahajan et al. article also reports a three-dimensional homology model suggesting an energetically favorable position of LFM-A13 docked within BTK's catalytic site <Reference id=31360/>.
iupac name: (Z)-2-cyano-N-(2,5-dibromophenyl)-3-hydroxybut-2-enamide
synonym: alpha-cyano-beta-hydroxy-beta-methyl-N-(2, 5-dibromophenyl)propenamide
synonym: α-cyano-beta-hydroxy-β-methyl-N-(2, 5-dibromophenyl)propenamide
approved: f
ligand name: LFM-A13
type: SyntheticOrganicLigand

luminespib
in ch i key: NDAZATDQFDPQBD-UHFFFAOYSA-N
in ch i: InChI=1S/C26H31N3O5/c1-4-27-26(32)24-23(18-7-5-17(6-8-18)15-29-9-11-33-12-10-29)25(34-28-24)20-13-19(16(2)3)21(30)14-22(20)31/h5-8,13-14,16,30-31H,4,9-12,15H2,1-3H3,(H,27,32)
comment: Luminespib (NVP-AUY922) is an intravenous HSP90 inhibitor with the potential to target a range of cancers. Discovered during a research collaboration with Novartis, Vernalis is now looking to partner the programme. We have drawn the structure as depicted in its INN record. Other chemistry resources show alternative tautomers. For example, PubChem CID 10096043 matches on CAS registry number, but is a structural tautomer.
synonym: NVP-AUY922
synonym: AUY922
approved: f
ligand name: luminespib
type: SyntheticOrganicLigand

SNX0723
in ch i key: GAGDTKJJVCLACJ-ZDUSSCGKSA-N
in ch i: InChI=1S/C22H26FN3O3/c1-12-10-26(17-8-22(2,3)9-18(27)19(12)17)14-6-15(23)20(21(24)28)16(7-14)25-13-4-5-29-11-13/h6-7,10,13,25H,4-5,8-9,11H2,1-3H3,(H2,24,28)/t13-/m0/s1
comment: SNX-2112 is an orally available, Hsp90 inhibitor that exhibits antitumour activity in vitro. It has an EC50 for inhibition of α-synuclein (αSyn) oligomerization of approximately 48 nM and was able to rescue αSyn-induced toxicity <Reference id=31357/>. This suggests its possible use in Parkinson's disease and other neurodegenerative disorders linked to protein misfolding. A more recent publication has looked at the specificity of this and other inhibitors between HSP90 paralogues <Reference id=31355/>. In another study this inhibitor also significantly reduced the cytotoxicity of NK cells by decreasing viability, inducing apoptosis and down-regulating the expression of cytokines and functional receptors, suggesting a potential immunosuppressant strategy <Reference id=15289/>.
iupac name: 2-fluoro-6-[[(3S)-oxolan-3-yl]amino]-4-(3,6,6-trimethyl-4-oxo-5,7-dihydroindol-1-yl)benzamide
xref: CHEMBL3104858
approved: f
ligand name: SNX0723
type: SyntheticOrganicLigand

SGC2085
canonical SMILES: Cc1cc(cc(c1)C)Oc1ccc(cc1C)CNC(=O)C(N)C
in ch i key: GLFOFXKMALJTCZ-HNNXBMFYSA-N
in ch i: InChI=1S/C19H24N2O2/c1-12-7-13(2)9-17(8-12)23-18-6-5-16(10-14(18)3)11-21-19(22)15(4)20/h5-10,15H,11,20H2,1-4H3,(H,21,22)/t15-/m0/s1
comment: SGC2085 is a selective inhibitor of the protein arginine N-methyltransferase, coactivator associated arginine methyltransferase 1, CARM1 (a.k.a. PRMT4) <Reference id=31354/>. PRMT4 is reported to be involved in neoplastic transformation in colorectal cancer, and in estrogen-stimulated breast cancer growth. The selectivity of SGC2085 provides a useful tool compound to validate this PRMT as a therapeutic target.
iupac name: (2S)-2-amino-N-{[4-(3,5-dimethylphenoxy)-3-methylphenyl]methyl}propanamide
synonym: compound 27 [PMID: 27390919]
approved: f
ligand name: SGC2085
type: SyntheticOrganicLigand

AM7499
in ch i key: OSVHLUXLWQLPIY-KBAYOESNSA-N
in ch i: InChI=1S/C24H36O5/c1-6-7-10-28-22(27)23(2,3)16-12-19(26)21-17-11-15(14-25)8-9-18(17)24(4,5)29-20(21)13-16/h12-13,15,17-18,25-26H,6-11,14H2,1-5H3/t15-,17-,18-/m1/s1
comment: AM7499 is a non-selective cannabinoid receptor agonist <Reference id=31353/>. It has been designed to be readily hydrolysed by plasma esterases (to shorten its duration of action; such compounds are being called 'controlled-deactivation cannabinoids') and to be less prone to deposition in bodily fat than existing classical cannabinoid agonists. This strategy has been adopted to produce cannabinoid agonists with improved drug-like qualities and potentially a more favourable safety profile.
iupac name: butyl 2-[(6aR,9R,10aR)-1-hydroxy-9-(hydroxymethyl)-6,6-dimethyl-6H,6aH,7H,8H,9H,10H,10aH-benzo[c]isochromen-3-yl]-2-methylpropanoate
synonym: compound 3b [PMID: 27367336]
approved: f
ligand name: AM7499
type: SyntheticOrganicLigand

AZD8848
in ch i key: FEFIBEHSXLKJGI-UHFFFAOYSA-N
in ch i: InChI=1S/C29H43N7O5/c1-3-4-16-41-28-32-26(30)25-27(33-28)36(29(38)31-25)13-7-12-35(11-6-10-34-14-17-40-18-15-34)21-23-9-5-8-22(19-23)20-24(37)39-2/h5,8-9,19H,3-4,6-7,10-18,20-21H2,1-2H3,(H,31,38)(H2,30,32,33)
comment: AZD8848 is an investigational agonist, selective for Toll-like receptor 7 (TLR7) <Reference id=31335/>. It is Example 2-37 claimed in patent US20140045837 <Reference id=31351/>.
iupac name: methyl 2-(3-(((3-(6-amino-2-butoxy-8-oxo-7,8-dihydro-9H-purin-9-yl)propyl)(3-morpholinopropyl)amino)methyl)phenyl)acetate
synonym: DSP-3025
approved: f
ligand name: AZD8848
type: SyntheticOrganicLigand

F16357
isomeric SMILES: Fc1ccc(cc1)CN1CCN(CC1)C(=O)/C=C/c1ccccc1Cl
in ch i key: RMDYFILMTQCLCQ-JXMROGBWSA-N
in ch i: InChI=1S/C20H20ClFN2O/c21-19-4-2-1-3-17(19)7-10-20(25)24-13-11-23(12-14-24)15-16-5-8-18(22)9-6-16/h1-10H,11-15H2/b10-7+
comment: Context of this referenced study is testing the F16357 antagonism of PAR1 in rat bladder under inflammatory conditions, in particular to prevent the pathophysiological symptoms of cyclophosphamide-induced interstitial cystitis (IC) <Reference id=31340/>.
iupac name: (E)-3-(2-chlorophenyl)-1-[4-[(4-fluorophenyl)methyl]piperazin-1-yl]prop-2-en-1-one
xref: CHEMBL559808
synonym: Example 1 in WO2007147824
synonym: Compound 39 [PMID: 19791800]
approved: f
ligand name: F16357
type: SyntheticOrganicLigand

GSK2245035
in ch i key: LFMPVTVPXHNXOT-HNNXBMFYSA-N
in ch i: InChI=1S/C20H34N6O2/c1-3-10-15(2)28-19-23-17(21)16-18(24-19)26(20(27)22-16)14-9-5-8-13-25-11-6-4-7-12-25/h15H,3-14H2,1-2H3,(H,22,27)(H2,21,23,24)/t15-/m0/s1
comment: GSK2245035 is reported as a selective Toll-like receptor 7 (TLR7) agonist, with potential clinical action as an intranasally administered anti-asthmatic <Reference id=31335/>. It is Example 22 claimed in patent WO2010018133 <Reference id=31336/>. The TLR7- IFNα pathway is a novel pathway being investigated for pharmacological intervention in allergic asthma.
iupac name: 6-amino-2-[(2S)-pentan-2-yloxy]-9-[5-(piperidin-1-yl)pentyl]-8,9-dihydro-7H-purin-8-one
synonym: compound 32 [PMID: 26861551]
approved: f
ligand name: GSK2245035
type: SyntheticOrganicLigand

compound 9 [PMID: 23472952]
canonical SMILES: OB(CCCCC(C(=O)O)(CCN1CCCCC1)N)O
isomeric SMILES: OB(CCCC[C@](C(=O)O)(CCN1CCCCC1)N)O
in ch i key: CHPILBYRQPOXMV-CYBMUJFWSA-N
in ch i: InChI=1S/C13H27BN2O4/c15-13(12(17)18,6-2-3-8-14(19)20)7-11-16-9-4-1-5-10-16/h19-20H,1-11,15H2,(H,17,18)/t13-/m1/s1
comment: Compound 9 is an experimental compound which inhibits the activity of arginases 1 and 2, (ARG1, ARG2) <Reference id=30564/>. In a rat model of myocardial ischemia/reperfusion injury (MI/RI), compound 9 reduces cardiac reperfusion injury <Reference id=30564/>.
iupac name: (2R)-2-amino-6-borono-2-(2-piperidin-1-ylethyl)hexanoic acid
xref: CHEMBL2326089
synonym: arginase inhibitor 1
approved: f
ligand name: compound 9 [PMID: 23472952]
type: SyntheticOrganicLigand

peptide 30 [PMID: 27019010]
in ch i key: CSHFHJNMIMPJST-HOTGVXAUSA-N
in ch i: InChI=1S/C20H30N4O5/c1-13(2)9-16(20(28)29-3)24-19(27)15(10-14-7-5-4-6-8-14)23-18(26)12-22-17(25)11-21/h4-8,13,15-16H,9-12,21H2,1-3H3,(H,22,25)(H,23,26)(H,24,27)/t15-,16-/m0/s1
comment: Peptide 30 is a synthetic tetrapeptide reported to occupy the arachadonic acid binding site of cyclooxygenase 2 (COX-2) to bring about enzyme inhibition with an antiinflammatory/analgesic outcome <Reference id=31333/>. Docking studies suggest that peptide 30 can occupy the active site of inducible nitric oxide synthase (iNOS; iNOS being well documented in pain mechanisms), although the COX-2 interaction is considered to be the major contributor to both the analgesic and antiinflammatory effects of the peptide in vivo.
iupac name: methyl (2S)-2-[[(2S)-2-[[2-[(2-aminoacetyl)amino]acetyl]amino]-3-phenylpropanoyl]amino]-4-methylpentanoate
approved: f
ligand name: peptide 30 [PMID: 27019010]
type: PeptideLigand

compound 24 [PMID: 26987013 ]
canonical SMILES: O=C1c2c(ccc(c2C(=O)N1c1ccc[n+](c1C)[O-])Cl)NS(=O)(=O)c1ccc(cc1)C(C)(C)C
isomeric SMILES: O=C1c2c(ccc(c2C(=O)N1c1ccc[n+](c1C)[O-])Cl)NS(=O)(=O)c1ccc(cc1)C(C)(C)C
in ch i key: SEZYEWZALINSCW-UHFFFAOYSA-N
comment: Compound 24 is one of the clinical lead C-C motif chemokine receptor 9 (CCR9) antagonists reported in <Reference id=31331/>. It is also one of the compounds claimed in patent WO2015097121 <Reference id=31332/>. CCR9 modulators (e.g. antagonists, partial agonists or inverse agonists) are of clinical interest for their potential to treat, prevent or ameliorate condtions such as inflammatory bowel disease (IBD), in which CCR9 activation is believed to be associated with the pathology. Compound 24 exhibits an improved pharmacokinetic (PK) profile compared to the prototype CCR9 antagonist <Ligand id=9046/>.
iupac name: 4-tert-butyl-N-[7-chloro-2-(2-methyl-1-oxidopyridin-1-ium-3-yl)-1,3-dioxoisoindol-4-yl]benzenesulfonamide
approved: f
ligand name: compound 24 [PMID: 26987013 ]
type: SyntheticOrganicLigand

compound 86 [PMID: 26982234]
in ch i key: VKLKXFOZNHEBSW-UHFFFAOYSA-N
in ch i: InChI=1S/C24H24N4O4/c25-23(29)19-13-22(15-26-14-19)32-16-17-2-1-3-20(12-17)27-24(30)18-4-6-21(7-5-18)28-8-10-31-11-9-28/h1-7,12-15H,8-11,16H2,(H2,25,29)(H,27,30)
comment: Compound 86 is reported as a selective inhibitor of sirtuin 2 (SIRT2) <Reference id=31324/>, a NAD-dependent protein deacetylase with protective effects neurodegenerative disease. Compound 86 is shown to be competitive with NAD+ and the enzyme's peptide substrate, with acceptable blood-brain barrier penetrance (a property essential for any drug being developed for neuroprotective activity). Drug-like SIRT2 inhibitors are being developed to determine if SIRT2 blockade could be of clinical benefit in Parkinson's disease <Reference id=31323/>.
iupac name: 5-({3-[4-(morpholin-4-yl)benzamido]phenyl}methoxy)pyridine-3-carboxamide
approved: f
ligand name: compound 86 [PMID: 26982234]
type: SyntheticOrganicLigand

rosiptor
canonical SMILES: NCC1C(CCC2(C1CCC2=C)C)C1(C)CCC(CC1CO)O
in ch i key: MDEJTPWQNNMAQF-BVMLLJBZSA-N
in ch i: InChI=1S/C20H35NO2/c1-13-4-5-17-16(11-21)18(7-9-19(13,17)2)20(3)8-6-15(23)10-14(20)12-22/h14-18,22-23H,1,4-12,21H2,2-3H3/t14-,15+,16+,17+,18+,19-,20+/m1/s1
comment: Rosiptor (AQX-1125) is an investigational allosteric activator of the SH2 domain-containing inositol 5'-phosphatase 1, SHIP1 (HGNC gene symbol INPP5D) <Reference id=31316/>. SHIP1 is a negative regulatory phosphatase in the PI3K pathway, a signalling pathway that plays a central role in cellular activation, proliferation, and survival, and which is strongly implicated in inflammatory disorders and cancer. Agonists that activate SHIP1 are being actively developed (as alternatives to direct PI3K inhibitors) for their potential anti-inflammatory action. AQX-1125 is claimed in patent WO2014158654, where it appears to be referred to as compound 9 (without the acetate) <Reference id=31318/>.
iupac name: (1S,3S,4R)-4-[(3aS,4R,5S,7aS)-4-(aminomethyl)-7a-methyl-1-methylidene-3,3a,4,5,6,7-hexahydro-2H-inden-5-yl]-3-(hydroxymethyl)-4-methylcyclohexan-1-ol
synonym: AQX1125
synonym: AQX-1125
approved: f
ligand name: rosiptor
type: SyntheticOrganicLigand

compound 9 [PMID: 26937601]
in ch i key: FNMJFZYRSQTKIH-HXPMCKFVSA-N
in ch i: InChI=1S/C19H19F3N6O2/c1-9-14(22)15(30-3)25-18(24-9)28-7-12-16(29)27(2)17(23)26-19(12,8-28)11-5-4-10(20)6-13(11)21/h4-6,12H,7-8H2,1-3H3,(H2,23,26)/t12-,19+/m0/s1
comment: This Merck BACE1 inhibitor, compound 9 (MBi-4), robustly lowers CSF and cortex Aβ40 in both rats and cynomolgus monkeys <Reference id=31047/>. The clinical status is unclear with respect to <Ligand id=8699/> from Merck in Phase III for which it could be a back-up. More details in this blogpost.
iupac name: (4aR,7aS)-2-amino-7a-(2,4-difluorophenyl)-6-(5-fluoro-4-methoxy-6-methylpyrimidin-2-yl)-3-methyl-5,7-dihydro-4aH-pyrrolo[3,4-d]pyrimidin-4-one
synonym: Mbi-4
approved: f
ligand name: compound 9 [PMID: 26937601]
type: SyntheticOrganicLigand

naquotinib
in ch i key: QKDCLUARMDUUKN-XMMPIXPASA-N
in ch i: InChI=1S/C30H42N8O3/c1-4-25-30(41-24-12-15-38(20-24)26(39)5-2)34-29(27(33-25)28(31)40)32-21-6-8-22(9-7-21)36-13-10-23(11-14-36)37-18-16-35(3)17-19-37/h5-9,23-24H,2,4,10-20H2,1,3H3,(H2,31,40)(H,32,34)/t24-/m1/s1
comment: ASP8273 is a third generation EGFR inhibitor, targeting T790M / L858R mutants. It is a structural match to example 54 in patent WO2013108754 <Reference id=31313/>.
iupac name: 6-ethyl-3-[4-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]anilino]-5-[(3R)-1-prop-2-enoylpyrrolidin-3-yl]oxypyrazine-2-carboxamide
synonym: ASP8273
approved: f
ligand name: naquotinib
type: SyntheticOrganicLigand

vamorolone
in ch i key: ZYTXTXAMMDTYDQ-DGEXFFLYSA-N
in ch i: InChI=1S/C22H28O4/c1-13-10-18-16-5-4-14-11-15(24)6-8-20(14,2)17(16)7-9-21(18,3)22(13,26)19(25)12-23/h6-8,11,13,16,18,23,26H,4-5,9-10,12H2,1-3H3/t13-,16-,18+,20+,21+,22+/m1/s1
comment: Vamorolone (VBP15) is a novel, oral non-hormonal steroid modulator, that is being investigated in Duchenne muscular dystrophy. It is a multi-functional drug that exhibits anti-inflammatory, membrane stabilisation, and mineralocorticoid receptor antagonist activities. Vamorolone is being proposed as a potential replacement for the corticosteroids that are currently used in DMD, as it appears to cause fewer of the common corticosteroids adverse effects <Reference id=40635/>.
iupac name: (8S,10S,13S,14S,16R,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-7,8,12,14,15,16-hexahydro-6H-cyclopenta[a]phenanthren-3-one
xref: CHEMBL2348780
synonym: VBP-15
synonym: VBP15
approved: f
ligand name: vamorolone
type: SyntheticOrganicLigand

upadacitinib
in ch i key: WYQFJHHDOKWSHR-MNOVXSKESA-N
in ch i: InChI=1S/C17H19F3N6O/c1-2-10-7-25(16(27)24-9-17(18,19)20)8-11(10)13-5-22-14-6-23-15-12(26(13)14)3-4-21-15/h3-6,10-11,21H,2,7-9H2,1H3,(H,24,27)/t10-,11+/m1/s1
comment: Upadacitinib (ABT-494) is a novel second generation orally active Janus kinase inhibitor with high JAK1 selectivity <Reference id=31310/><Reference id=37882/>. The chemical structure is claimed as compound 1 in Abbvie's patent WO2015061665 <Reference id=31310/>. It was developed for potential clinical efficacy in multiple autoimmune diseases. Its first approval was for the treatment of rheumatoid arthritis <Reference id=38446/>.
synonym: ABT-494
synonym: Rinvoq®
approved: t
ligand name: upadacitinib
type: SyntheticOrganicLigand

EPZ020411
in ch i key: QMDKVNSQXPVCRD-UHFFFAOYSA-N
in ch i: InChI=1S/C25H38N4O3/c1-26-10-11-29(2)18-21-17-27-28-25(21)20-3-5-22(6-4-20)32-24-15-23(16-24)31-14-9-19-7-12-30-13-8-19/h3-6,17,19,23-24,26H,7-16,18H2,1-2H3,(H,27,28)
comment: EPZ020411 is a research tool compound which is a potent, and selective inhibitor of protein arginine methyltransferase 6 (PRMT6) <Reference id=31302/>.
iupac name: N,N'-dimethyl-N'-[[5-[4-[3-[2-(oxan-4-yl)ethoxy]cyclobutyl]oxyphenyl]-1H-pyrazol-4-yl]methyl]ethane-1,2-diamine
approved: f
ligand name: EPZ020411
type: SyntheticOrganicLigand

UCM1014
canonical SMILES: CCC(=O)NCC1CCc2c(N1Cc1ccccc1)cccc2OC
isomeric SMILES: CCC(=O)NCC1CCc2c(N1Cc1ccccc1)cccc2OC
in ch i key: VLPGTHUDTCBGRU-UHFFFAOYSA-N
in ch i: InChI=1S/C21H26N2O2/c1-3-21(24)22-14-17-12-13-18-19(10-7-11-20(18)25-2)23(17)15-16-8-5-4-6-9-16/h4-11,17H,3,12-15H2,1-2H3,(H,22,24)
comment: Molecular superpositions on previously developed pharmacophore models predicted a suitable position for a methoxy group on a tetrahydroquinoline ring. This lead to the optimisation of a benzyl derivative 8a (UCM1014) with a melatonin receptor MT2 Ki of 0.001 nM and more than 10000-fold selectivity over MT1, as a full agonist tool compound <Reference id=31263/>. This is compared with other modulators in a recent melatonin receptor review <Reference id=31264/>.
iupac name: N-[(1-benzyl-5-methoxy-1,2,3,4-tetrahydroquinolin-2-yl)methyl]propanamide
synonym: Compound 8a [PMID 26334942]
approved: f
ligand name: UCM1014
type: SyntheticOrganicLigand

lisofylline
canonical SMILES: CC(CCCCn1c(=O)c2n(C)cnc2n(c1=O)C)O
isomeric SMILES: C[C@H](CCCCn1c(=O)c2n(C)cnc2n(c1=O)C)O
in ch i key: NSMXQKNUPPXBRG-SECBINFHSA-N
in ch i: InChI=1S/C13H20N4O3/c1-9(18)6-4-5-7-17-12(19)10-11(14-8-15(10)2)16(3)13(17)20/h8-9,18H,4-7H2,1-3H3/t9-/m1/s1
comment: Lisophylline is an active metabolite of <Ligand id=7095/>. The compound has novel anti-inflammatory properties, likely through inhibition of IL-12 signalling and STAT-4 activation <Reference id=31240/>. It is reported to prevent type 1 diabetes in preclinical models <Reference id=31242/> and improve the function and viability of isolated or transplanted pancreatic islets <Reference id=31241/>. Evidence suggests that combined treatment with lisofylline (for its anti-inflammatory action) and exendin-4 (to enhance beta-cell proliferation) can reverse autoimmune diabetes in the non-obese diabetic (NOD) mouse model <Reference id=31243/>.
iupac name: 1-[(5R)-5-hydroxyhexyl]-3,7-dimethylpurine-2,6-dione
xref: CHEMBL1411
synonym: CT-1501R
synonym: (R)-lisophylline
approved: f
ligand name: lisofylline
type: SyntheticOrganicLigand

TX2-121-1
in ch i key: GKJWHLDKQULMHJ-PZMWFESPSA-N
in ch i: InChI=1S/C42H52N8O3/c1-3-36(51)47-34-22-31(9-10-35(34)53-33-7-5-4-6-8-33)38-37-39(43)45-26-46-40(37)50(48-38)32-12-16-49(17-13-32)18-15-44-41(52)27(2)11-14-42-23-28-19-29(24-42)21-30(20-28)25-42/h3-10,22,26-30,32H,1,11-21,23-25H2,2H3,(H,44,52)(H,47,51)(H2,43,45,46)/t27-,28?,29?,30?,42?/m1/s1
comment: TX2-121-1 is a functional analogue of <Ligand id=9241/> <Reference id=31301/>. It acts to inhibit HER3-dependent signalling and growth, likely due to the effect of the conjugated hydrophobic adamantine group which is believed to target HER3 for proteasome-mediated degradation. Targeted degradation reduces the amount of HER3 available to form the HER3 heterodimers believed to be required for cellular activity.
iupac name: (2R)-4-(1-adamantyl)-N-[2-[4-[4-amino-3-[4-phenoxy-3-(prop-2-enoylamino)phenyl]pyrazolo[3,4-d]pyrimidin-1-yl]piperidin-1-yl]ethyl]-2-methylbutanamide
synonym: conjugate 2e [PMID: 26094118]
approved: f
ligand name: TX2-121-1
type: SyntheticOrganicLigand

TX1-85-1
in ch i key: FYICDSWKKFSYOM-UHFFFAOYSA-N
in ch i: InChI=1S/C32H36N8O3/c1-3-28(42)36-26-19-22(9-14-27(26)43-25-7-5-4-6-8-25)30-29-31(33)34-20-35-32(29)40(37-30)24-12-10-23(11-13-24)39-17-15-38(16-18-39)21(2)41/h3-9,14,19-20,23-24H,1,10-13,15-18H2,2H3,(H,36,42)(H2,33,34,35)
comment: TX1-85-1 is reported as a selective, irreversible ERBB3 (HER3) ligand <Reference id=31301/><Reference id=31794/>. The ligand binds covalently to Cys721 located in the enzyme's ATP-binding site, a position unique to ERBB3, compared to all other kinases. It was tested in preclinical studies.
iupac name: N-[5-[1-[4-(4-acetylpiperazin-1-yl)cyclohexyl]-4-aminopyrazolo[3,4-d]pyrimidin-3-yl]-2-phenoxyphenyl]prop-2-enamide
synonym: TX-85-1
approved: f
ligand name: TX1-85-1
type: SyntheticOrganicLigand

AGI-5198
in ch i key: FNYGWXSATBUBER-UHFFFAOYSA-N
in ch i: InChI=1S/C27H31FN4O2/c1-19-9-6-7-14-24(19)26(27(34)30-22-11-4-3-5-12-22)32(23-13-8-10-21(28)17-23)25(33)18-31-16-15-29-20(31)2/h6-10,13-17,22,26H,3-5,11-12,18H2,1-2H3,(H,30,34)
comment: AGI-5198 is a selective inhibitor of R132H mutated metabolic enzyme, isocitrate dehydrogenase 1 (IDH1) <Reference id=31206/>. R132H is a mutation found in multiple human cancers which is responsible for the generation of the oncometabolite R-2-hydroxyglutarate (R-2HG). Inhibition of R132H IDH1 is being examined for antineoplastic activity. This corresponds to example 165 in a patent from Agios <Reference id=31399/> who also filed on <Ligand id=9217/> (but both with binned activity values). This has a Probe Portal entry SGC AGI-5198.
iupac name: N-cyclohexyl-2-(3-fluoro-N-[2-(2-methylimidazol-1-yl)acetyl]anilino)-2-(2-methylphenyl)acetamide
xref: CHEMBL2180727
approved: f
ligand name: AGI-5198
type: SyntheticOrganicLigand

ZCZ011
in ch i key: RJSPNRDBWHHFMH-UHFFFAOYSA-N
in ch i: InChI=1S/C21H18N2O2S/c1-14-9-10-16-18(12-14)22-21(15-6-3-2-4-7-15)20(16)17(13-23(24)25)19-8-5-11-26-19/h2-12,17,22H,13H2,1H3
comment: ZCZ011 was synthesized as a possible positive allosteric modulator (PAM) of the cannabinoid CB1 receptor <Reference id=31305/><Reference id=31309/>. It has subsequently been described as an ago-PAM, which is a ligand that displays both direct agonist activity and PAM activity <Reference id=38570/>. It is a derivative of the confirmed CB1 receptor ago-PAM <Ligand id=10272/>.
iupac name: 6-methyl-3-(2-nitro-1-(thiophen-2-yl)ethyl)-2-phenyl-1H-indole
synonym: ZCZ-011
synonym: ZCZ 011
approved: f
ligand name: ZCZ011
type: SyntheticOrganicLigand

compound 27f [PMID: 25625617]
in ch i key: LVBWRNKEBGYENR-UHFFFAOYSA-N
in ch i: InChI=1S/C26H31F3N6O2/c1-25(2,26(27,28)29)33-22-13-20(30-14-16-9-11-37-12-10-16)23-31-15-21(35(23)34-22)17-3-5-18(6-4-17)24(36)32-19-7-8-19/h3-6,13,15-16,19,30H,7-12,14H2,1-2H3,(H,32,36)(H,33,34)
comment: Compound 27f is an orally active, potent and selective chemical probe inhibitor of TTK protein kinase (a.k.a. MPS1) <Reference id=31296/>.
xref: CHEMBL3410084
approved: f
ligand name: compound 27f [PMID: 25625617]
type: SyntheticOrganicLigand

GAT100
in ch i key: OZEQTGDZTPJNAR-UHFFFAOYSA-N
in ch i: InChI=1S/C25H28N4OS/c1-2-21-22-16-20(31-17-26)10-11-23(22)28-24(21)25(30)27-13-12-18-6-8-19(9-7-18)29-14-4-3-5-15-29/h6-11,16,28H,2-5,12-15H2,1H3,(H,27,30)
comment: GAT100 is a potent negative allosteric modulator (NAM) of the cannabinoid CB1 receptor, which exhibits irreversible binding <Reference id=31303/><Reference id=31308/>. GAT100 can be utilised as a covalent probe for mapping structure-function characteristics, which define the druggable CB1 receptor allosteric binding site. GAT100 is one of the compounds claimed in patent WO2015027160 <Reference id=31304/>.
iupac name: 3-Ethyl-5-isothiocyanato-N-[4-(piperidin-1-yl)phenethyl]-1H-indole-2-carboxamide
synonym: 5-(cyanosulfanyl)-3-ethyl-N-{2-[4-(piperidin-1-yl)phenyl]ethyl}-1H-indole-2-carboxamide
approved: f
ligand name: GAT100
type: SyntheticOrganicLigand

nonabine
in ch i key: YHUDSHIRWOVVCV-UHFFFAOYSA-N
in ch i: InChI=1S/C25H33NO2/c1-6-7-8-9-17(2)18(3)20-14-22(27)24-21(19-10-12-26-13-11-19)16-25(4,5)28-23(24)15-20/h10-18,27H,6-9H2,1-5H3
comment: Nonabine is a selective cannabinoid CB1 receptor agonist, investigated for its antiemetic action.
iupac name: 2,2-dimethyl-7-(3-methyloctan-2-yl)-4-pyridin-4-ylchromen-5-ol
xref: CHEMBL2106841
synonym: BRL-4664
synonym: BRL 4664
approved: f
ligand name: nonabine
type: SyntheticOrganicLigand

ibipinabant
in ch i key: AXJQVVLKUYCICH-OAQYLSRUSA-N
comment: Ibipinabant is a selective cannabinoid CB1 receptor antagonist <Reference id=31288/>, investigated for its clinical potential as an anti-obesity drug.
iupac name: (4S)-3-(4-chlorophenyl)-N-(4-chlorophenyl)sulfonyl-N'-methyl-4-phenyl-4,5-dihydropyrazole-1-carboximidamide
xref: CHEMBL412262
synonym: SLV319
synonym: SLV-319
synonym: BMS-646256
approved: f
ligand name: ibipinabant
type: SyntheticOrganicLigand

surinabant
in ch i key: HMXDWDSNPRNUKI-UHFFFAOYSA-N
comment: Surinabant is a selective, orally active cannabinoid CB1 receptor antagonist <Reference id=31287/>, investigated for potential use as an aid to smoking cessation. CB1 receptor antagonists may have clinical potential in other addictions (e.g. alcoholism <Reference id=31285/>) or conditions such as attention deficit hyperactivity disorder (ADHD) <Reference id=31286/>.
iupac name: 5-(4-bromophenyl)-1-(2,4-dichlorophenyl)-4-ethyl-N-piperidin-1-ylpyrazole-3-carboxamide
xref: CHEMBL189676
synonym: SR-147778
synonym: SR147778
synonym: SR 147778
approved: f
ligand name: surinabant
type: SyntheticOrganicLigand

otenabant
in ch i key: UNAZAADNBYXMIV-UHFFFAOYSA-N
in ch i: InChI=1S/C25H25Cl2N7O/c1-2-31-25(24(28)35)11-13-33(14-12-25)22-20-23(30-15-29-22)34(17-9-7-16(26)8-10-17)21(32-20)18-5-3-4-6-19(18)27/h3-10,15,31H,2,11-14H2,1H3,(H2,28,35)
comment: Otenabant is a selective cannabinoid CB1 receptor antagonist, which was investigated in clinical trials (as the hydrochloride salt - PubChem CID 16223963) for its potential anorectic action in the treatment of obesity.
iupac name: 1-[8-(2-chlorophenyl)-9-(4-chlorophenyl)purin-6-yl]-4-ethylaminopiperidine-4-carboxamide
xref: CHEMBL562668
synonym: CP-945598
synonym: CP-945,598
approved: f
ligand name: otenabant
type: SyntheticOrganicLigand

taranabant
in ch i key: QLYKJCMUNUWAGO-GAJHUEQPSA-N
comment: Taranabant is a cannabinoid CB1 receptor antagonist/inverse agonist <Reference id=31281/><Reference id=31283/>, with anorectic action. It was investigated for its potential as a novel weight management therapeutic in obese and overweight patients.
iupac name: N-[(2S,3S)-4-(4-chlorophenyl)-3-(3-cyanophenyl)butan-2-yl]-2-methyl-2-[5-(trifluoromethyl)pyridin-2-yl]oxypropanamide
xref: CHEMBL220360
synonym: MK-0364
synonym: MK 0364
synonym: MK0364
approved: f
ligand name: taranabant
type: SyntheticOrganicLigand

compound 6j [PMID: 27219676]
in ch i key: CMJJZRAAQMUAFH-INIZCTEOSA-N
in ch i: InChI=1S/C26H23F3N6O/c1-16-11-34(23-9-30-14-31-10-23)13-19-5-18(3-4-24(16)19)25(36)33-21-6-20(26(27,28)29)7-22(8-21)35-12-17(2)32-15-35/h3-10,12,14-16H,11,13H2,1-2H3,(H,33,36)/t16-/m0/s1
comment: Compound 6j is a preclinical, orally available and selective inhibitor of discoidin domain receptor 1 (DDR1) <Reference id=31275/>. The compound has a favourable pharmacokinetic profile.
iupac name: (4R)-4-methyl-N-[3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl]-2-(pyrimidin-5-yl)-1,2,3,4-tetrahydroisoquinoline-7-carboxamide
approved: f
ligand name: compound 6j [PMID: 27219676]
type: SyntheticOrganicLigand

ravoxertinib
in ch i key: RZUOCXOYPYGSKL-GOSISDBHSA-N
comment: Ravoxertinib (GDC-0994) is an orally available, small molecule selective inhibitor of extracellular signal-regulated kinase 1/2 (ERK1/2) in early clinical development <Reference id=31273/>. It is compound 22 in <Reference id=31273/>. ERK1 is formally known as mitogen-activated protein kinase 3 (MAPK3) and ERK2 as mitogen-activated protein kinase 1 (MAPK1). GDC-0994 is example 39 claimed in patent WO2013130976 <Reference id=31274/>.
iupac name: 1-[(1S)-1-(4-chloro-3-fluorophenyl)-2-hydroxyethyl]-4-[2-[(2-methylpyrazol-3-yl)amino]pyrimidin-4-yl]pyridin-2-one
xref: CHEMBL3544964
synonym: example 39 [WO2013130976]
synonym: GDC-0994
approved: f
ligand name: ravoxertinib
type: SyntheticOrganicLigand

PF-06767832
in ch i key: VVZZHFMLRHJXTO-RXVVDRJESA-N
in ch i: InChI=1S/C22H23N3O3S/c1-14-10-23-19(22(27)25-18-6-7-28-11-21(18)26)9-17(14)8-15-2-4-16(5-3-15)20-12-29-13-24-20/h2-5,9-10,12-13,18,21,26H,6-8,11H2,1H3,(H,25,27)/t18-,21-/m0/s1
comment: PF-06767832 (compound 38) is an orally bioavailable, positive allosteric modulator (PAM) selective for the M1 muscarinic acetylcholine receptor (CHRM1) <Reference id=31270/>. It is one of the compounds claimed in patent WO2016009297 <Reference id=31271/>. M1 receptor PAMs are being designed for their potential to provide novel therapies for the treatment of M1-mediated diseases and disorders such as Alzheimer's disease.
iupac name: N-[(3R,4S)-3-hydroxyoxan-4-yl]-5-methyl-4-[[4-(1,3-thiazol-4-yl)phenyl]methyl]pyridine-2-carboxamide
approved: f
ligand name: PF-06767832
type: SyntheticOrganicLigand

CC-885
in ch i key: DOEVCIHTTTYVCC-UHFFFAOYSA-N
in ch i: InChI=1S/C22H21ClN4O4/c1-12-2-4-15(9-17(12)23)25-22(31)24-10-13-3-5-16-14(8-13)11-27(21(16)30)18-6-7-19(28)26-20(18)29/h2-5,8-9,18H,6-7,10-11H2,1H3,(H2,24,25,31)(H,26,28,29)
comment: Structural studies have shown that thalidomide class immunomodulatory drugs bind in a shallow hydrophobic pocket on the surface of cereblon, that is mediated by a glutarimide ring of the ligand. Binding of small molecules to cereblon can alter its substrate specificity <Reference id=37806/>. Thalidomide and its related drugs enhance recruitment of Ikaros and Aiolos to the E3 ubiquitin ligase complex. CC-885 has a different mechanism of action compared to <Ligand id=7327/>, <Ligand id=7331/> and <Ligand id=7348/>. The anti-tumour activity of CC-885 is mediated through the cereblon-dependent ubiquitination and degradation of the translation termination factor GSPT1. Patient-derived acute myeloid leukaemia tumour cells exhibit high sensitivity to CC-885, indicating the clinical potential of this mechanism <Reference id=31228/>.
iupac name: 3-(3-chloro-4-methylphenyl)-1-[[2-(2,6-dioxopiperidin-3-yl)-1-oxo-3H-isoindol-5-yl]methyl]urea
approved: f
ligand name: CC-885
type: SyntheticOrganicLigand

compound 16 [PMID: 26794040]
in ch i key: WCDFXVWDGHHCSI-UHFFFAOYSA-N
in ch i: InChI=1S/C31H35FN2O6/c1-20(2)18-31(38)13-14-34(19-31)29(37)33-23-15-26(17-27(16-23)40-25-11-7-22(32)8-12-25)39-24-9-5-21(6-10-24)30(3,4)28(35)36/h5-12,15-17,20,38H,13-14,18-19H2,1-4H3,(H,33,37)(H,35,36)
comment: Compound 16 is a novel, potent and selective sphingosine-1-phosphate receptor 2 (S1P2 receptor) antagonist <Reference id=31226/>. The series of compounds including 16 is claimed in patent WO2013047701 <Reference id=31227/>.
iupac name: 2-[4-[3-(4-fluorophenoxy)-5-[[3-hydroxy-3-(2-methylpropyl)pyrrolidine-1-carbonyl]amino]phenoxy]phenyl]-2-methylpropanoic acid
approved: f
ligand name: compound 16 [PMID: 26794040]
type: SyntheticOrganicLigand

EAI045
in ch i key: YTUFHOKUFOQRDF-UHFFFAOYSA-N
in ch i: InChI=1S/C19H14FN3O3S/c20-12-5-6-15(24)14(9-12)16(17(25)22-19-21-7-8-27-19)23-10-11-3-1-2-4-13(11)18(23)26/h1-9,16,24H,10H2,(H,21,22,25)
comment: EAI045 is an allosteric inhibitor of mutant forms of the EGFR found in lung cancers whilst sparing the wild-type receptor <Reference id=31224/>. Allosteric inhibitors are being developed to overcome acquired resistance to current EGFR tyrosine kinase inhibitors which bind to the ATP pocket of the enzyme, which is the location of the many identified resistance mutations.
iupac name: 2-(5-fluoro-2-hydroxyphenyl)-2-(1-oxo-2,3-dihydro-1H-isoindol-2-yl)-N-(1,3-thiazol-2-yl)acetamide
approved: f
ligand name: EAI045
type: SyntheticOrganicLigand

2'3'-cGAMP
in ch i key: XRILCFTWUCUKJR-INFSMZHSSA-N
comment: 2'3'-cGAMP is produced in mammalian cells by the action of cyclic guanosine monophosphate (GMP)-adenosine monophosphate (AMP) synthase (cGAS) upon detection of double-stranded DNA in the cytosol that originates for example, from tumours or viruses. It is the endogenous agonist of the human STING protein <Reference id=31053/>, but appears not to activate mouse Sting. STING activation at the endoplasmic reticulum triggers type-I IFNs production by the innate immune response <Reference id=31054/>.
synonym: cyclic [G(2',5')pA(3',5')p]
synonym: Cyclic guanosine monophosphate-adenosine monophosphate
synonym: cyclic GMP-AMP
approved: f
ligand name: 2'3'-cGAMP
type: SyntheticOrganicLigand

compstatin
in ch i key: RDTRHBCZFDCUPW-KWICJJCGSA-N
comment: Compstatin is a cyclic 13 amino acid peptide inhibitor of complement component 3 (C3) <Reference id=31210/><Reference id=31212/>. Compstatin and analogues are being examined for immunomodulatory activity <Reference id=31211/><Reference id=31213/><Reference id=31214/> in inflammatory and degenerative diseases <Reference id=31216/>.
iupac name: 2-[(4R,7S,10S,13S,19S,22S,25S,28S,31S,34R)-4-[[(2S,3R)-1-amino-3-hydroxy-1-oxobutan-2-yl]carbamoyl]-34-[[(2S,3S)-2-amino-3-methylpentanoyl]amino]-25-(3-amino-3-oxopropyl)-7-[3-(diaminomethylideneamino)propyl]-10,13-bis(1H-imidazol-5-ylmethyl)-19-(1H-indol-3-ylmethyl)-6,9,12,15,18,21,24,27,30,33-decaoxo-28,31-di(propan-2-yl)-1,2-dithia-5,8,11,14,17,20,23,26,29,32-decazacyclopentatriacont-22-yl]acetic acid
xref: CHEMBL266963
approved: f
ligand name: compstatin
type: PeptideLigand

ivosidenib
in ch i key: WIJZXSAJMHAVGX-DHLKQENFSA-N
comment: Ivosidenib (AG-120) is an orally active, selective inhibitor of isocitrate dehydrogenase 1 (IDH1) <Reference id=34695/>, in particular with activity against IDH1 R132H or R132C mutants. It is one of the compounds claimed in Agios' patent WO2013107291, where it is Compound 176 <Reference id=31205/>. It is structurally related to <Ligand id=9240/> also from Agios.
iupac name: (2S)-N-[(1S)-1-(2-chlorophenyl)-2-[(3,3-difluorocyclobutyl)amino]-2-oxoethyl]-1-(4-cyanopyridin-2-yl)-N-(5-fluoropyridin-3-yl)-5-oxopyrrolidine-2-carboxamide
synonym: Tibsovo®
synonym: AG-120
synonym: AG120
synonym: AG 120
approved: t
ligand name: ivosidenib
type: SyntheticOrganicLigand

periciazine
in ch i key: LUALIOATIOESLM-UHFFFAOYSA-N
in ch i: InChI=1S/C21H23N3OS/c22-15-16-6-7-21-19(14-16)24(18-4-1-2-5-20(18)26-21)11-3-10-23-12-8-17(25)9-13-23/h1-2,4-7,14,17,25H,3,8-13H2
comment: Periciazine is a phenothiazine antipsychotic. It has anti-dopaminergic, adrenolytic, anticholinergic, metabolic and endocrine effects.
iupac name: 10-[3-(4-hydroxypiperidin-1-yl)propyl]phenothiazine-2-carbonitrile
xref: CHEMBL251940
synonym: pericyazine
synonym: RP-8909
synonym: propericiazine
approved: t
ligand name: periciazine
type: SyntheticOrganicLigand

benperidol
in ch i key: FEBOTPHFXYHVPL-UHFFFAOYSA-N
in ch i: InChI=1S/C22H24FN3O2/c23-17-9-7-16(8-10-17)21(27)6-3-13-25-14-11-18(12-15-25)26-20-5-2-1-4-19(20)24-22(26)28/h1-2,4-5,7-10,18H,3,6,11-15H2,(H,24,28)
comment: Benperidol is a butyrophenone antipsychotic, with general properties similar to those of <Ligand id=86/>.
iupac name: 3-[1-[4-(4-fluorophenyl)-4-oxobutyl]piperidin-4-yl]-1H-benzimidazol-2-one
xref: CHEMBL297302
synonym: Anquil®
synonym: R-4584
synonym: MCN-JR-4584
approved: t
ligand name: benperidol
type: SyntheticOrganicLigand

rotigaptide
in ch i key: GFJRASPBQLDRRY-TWTQBQJDSA-N
in ch i: InChI=1S/C28H39N7O9/c1-15(25(41)30-12-23(29)39)32-24(40)13-31-26(42)22-11-19(38)14-35(22)28(44)21-4-3-9-34(21)27(43)20(33-16(2)36)10-17-5-7-18(37)8-6-17/h5-8,15,19-22,37-38H,3-4,9-14H2,1-2H3,(H2,29,39)(H,30,41)(H,31,42)(H,32,40)(H,33,36)/t15-,19+,20-,21-,22-/m1/s1
comment: Rotigaptide is a hexapeptide developed originally by Wyeth, as an anti-arrhythmic agent. It promotes electrical coupling between ventricular myocytes by increasing gap junction conductance <Reference id=31073/>. A recent study showed reduction in myocardial infarction size in a porcine model and protection from IRI-related endothelial dysfunction in man. Rotigaptide may thus have therapeutic potential in the treatment of myocardial infarction <Reference id=31072/>.
iupac name: (2R,4S)-1-[(2R)-1-[(2R)-2-acetamido-3-(4-hydroxyphenyl)propanoyl]pyrrolidine-2-carbonyl]-N-[2-[[(2R)-1-[(2-amino-2-oxoethyl)amino]-1-oxopropan-2-yl]amino]-2-oxoethyl]-4-hydroxypyrrolidine-2-carboxamide
xref: ChEMBL450656
synonym: ZP-123
synonym: GAP-134
synonym: Dipeptide 9f [PMID 19175320]
approved: f
ligand name: rotigaptide
type: PeptideLigand

C108297
in ch i key: OMKDFVUMRKROMY-SSEXGKCCSA-N
in ch i: InChI=1S/C30H36FN3O4S/c1-29(2,3)23-5-11-27(12-6-23)39(35,36)33-14-13-24-17-28-22(18-30(24,20-33)21-38-16-15-37-4)19-32-34(28)26-9-7-25(31)8-10-26/h5-12,17,19H,13-16,18,20-21H2,1-4H3/t30-/m1/s1
comment: C108297 is a selective glucocorticoid receptor (GR) modulator, which attenuates obesity by reducing caloric intake and increasing lipolysis and fat oxidation. In addition, it attenuates inflammation by reduced macrophage infiltration and pro-inflammatory cytokine expression in white adipose tissue (WAT), as well as in vitro LPS-stimulated TNFα secretion in macrophage RAW 264.7 cells <Reference id=30998/>. C108297 was originally reported as compound 52 <Reference id=30999/>.
iupac name: (4aR)-6-(4-tert-butylphenyl)sulfonyl-1-(4-fluorophenyl)-4a-(2-methoxyethoxymethyl)-4,5,7,8-tetrahydropyrazolo[3,4-g]isoquinoline
xref: CHEMBL270575
synonym: Compound 52 [PMID:18226897]
approved: f
ligand name: C108297
type: SyntheticOrganicLigand

ARN726
canonical SMILES: O=C(NC1CNC1=O)OCCCCC1CCCCC1
isomeric SMILES: O=C(N[C@H]1CNC1=O)OCCCCC1CCCCC1
in ch i key: FNLUJRBWJBUJTC-LBPRGKRZSA-N
in ch i: InChI=1S/C14H24N2O3/c17-13-12(10-15-13)16-14(18)19-9-5-4-8-11-6-2-1-3-7-11/h11-12H,1-10H2,(H,15,17)(H,16,18)/t12-/m0/s1
comment: ARN726 is from a series of β-lactam derivatives that are potent, selective, and systemically active inhibitors of intracellular N-Acylethanolamine acid amidase (NAAA) by covalently binding the enzyme's catalytic cysteine. It exhibits anti-inflammatory effects in both mouse models and human macrophages <Reference id=30996/>. In the corresponding patent <Reference id=30997/> the structure seems to be example 5. There is a patchy SAR table for 106 structures on page 104 of the WO2014144836 PDF. The R isomer of this structure PubChem CID 86282216 is reported to be less active.
iupac name: 4-cyclohexylbutyl N-[(3S)-2-oxoazetidin-3-yl]carbamate
synonym: compound 6 [PMID: 25874594]
synonym: ARN-726
approved: f
ligand name: ARN726
type: SyntheticOrganicLigand

selegiline
canonical SMILES: CC(N(CC#C)C)Cc1ccccc1
isomeric SMILES: C[C@@H](N(CC#C)C)Cc1ccccc1
in ch i key: MEZLKOACVSPNER-GFCCVEGCSA-N
in ch i: InChI=1S/C13H17N/c1-4-10-14(3)12(2)11-13-8-6-5-7-9-13/h1,5-9,12H,10-11H2,2-3H3/t12-/m1/s1
comment: Marketed formulations may contain (PubChem CID 26758).
iupac name: methyl(1-phenylpropan-2-yl)(prop-2-yn-1-yl)amine
xref: CHEMBL972
synonym: Otrasel®
synonym: Selegene®
synonym: Deprenyl
synonym: L-deprenalin
synonym: Apo-Selegiline
synonym: Carbex
synonym: Emsam
synonym: Gen-Selegiline
synonym: Jumex
synonym: Novo-Selegiline
synonym: Nu-Selegiline
synonym: Sd Deprenyl
synonym: Eldepryl®
synonym: Zelapar®
synonym: L-deprenyl
approved: t
ligand name: selegiline
type: SyntheticOrganicLigand

RapaLink-1
in ch i key: QDOGZMBPRITPMZ-LFEDRMHTSA-N
comment: RapaLink-1 is a new-generation bivalent (bitopic) mTOR inhibitor, comprising a rapamycin-FRB-binding element (<Ligand id=6031/>, a.k.a. rapamycin) linked to an ATP binding site competitive TORKi (<Ligand id=7933/>, a.k.a. MLN0128) via a PEG linker <Reference id=31067/>. RapaLink-1 is able to overcome resistance to TORKis of mutant mTOR proteins in vitro, inhibiting proliferation MCF-7 cells at levels comparable to rapamycin or a combination of rapamycin and MLN0128.
synonym: 40-O-(2-((1-(32-(4-amino-3-(2-aminobenzo[d]oxazol-5-yl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-27-oxo-3,6,9,12,15,18,21,24-octaoxa-28-azadotriacontyl)-1H-1,2,3-triazol-4-yl)methoxy)ethyl)-rapamycin
approved: f
ligand name: RapaLink-1
type: SyntheticOrganicLigand

semapimod
isomeric SMILES: O=C(Nc1cc(cc(c1)/C(=N/N=C(N)N)/C)/C(=N/N=C(N)N)/C)CCCCCCCCC(=O)Nc1cc(cc(c1)/C(=N/N=C(N)N)/C)/C(=N/N=C(N)N)/C
in ch i key: PWDYHMBTPGXCSN-BFKCERSTSA-N
in ch i: InChI=1S/C34H52N18O2/c1-19(45-49-31(35)36)23-13-24(20(2)46-50-32(37)38)16-27(15-23)43-29(53)11-9-7-5-6-8-10-12-30(54)44-28-17-25(21(3)47-51-33(39)40)14-26(18-28)22(4)48-52-34(41)42/h13-18H,5-12H2,1-4H3,(H,43,53)(H,44,54)(H4,35,36,49)(H4,37,38,50)(H4,39,40,51)(H4,41,42,52)/b45-19-,46-20+,47-21-,48-22+
comment: Semapimod is an experimental anti-inflammatory compound. Structurally it is a tetravalent guanylhydrazone. The endoplasmic reticulum-localized chaperone gp96 (HSP90B1; P14625), which is involved in the biogenesis of Toll-like receptors (TLRs), is reported to be a molecular target of semapimod <Reference id=31066/>. Note that we have drawn the molecule as specified by the IUPAC name submitted to the WHO as proposed INN (list 89). CHEMBL2107779 and PubChem CID 5745214 represent alternative tautomers.
synonym: CNI-1493
approved: f
ligand name: semapimod
type: SyntheticOrganicLigand

ulixertinib
in ch i key: KSERXGMCDHOLSS-LJQANCHMSA-N
comment: Ulixertinib is an orally available, ATP-competitive inhibitor of the serine/threonine kinases extracellular signal-regulated kinase (ERK) 1 (MAPK3) and 2 (MAPK1), being investigated for anticancer activity in solid tumours and hematological malignancies carrying mutations in the MAPK signaling pathway, which renders them highly reliant on ERK for survival and growth. It is being developed by BioMed Valley Discoveries. This is one of the compounds claimed in patent WO2005113541 <Reference id=31063/>, where it is identified as I-9. The INN record specifies the (1S) stereoisomer as ulixertinib.
iupac name: N-[(1S)-1-(3-chlorophenyl)-2-hydroxyethyl]-4-[5-chloro-2-(propan-2-ylamino)pyridin-4-yl]-1H-pyrrole-2-carboxamide
synonym: BVD-523
synonym: BVD523
synonym: VRT-752271
synonym: VRT752271
approved: f
ligand name: ulixertinib
type: SyntheticOrganicLigand

G10 [PMID: 26646986]
in ch i key: NAGKYJATVFXZKN-UHFFFAOYSA-N
comment: The discovery of the so-called STING agonist G10 by high throughput in vitro screening is reported in <Reference id=31052/>. However, the authors could find no evidence of direct G10 binding to STING, despite experiments showing it being essential for the antiviral effects of the compound. The identity of the protein or factor engaged by G10 which stimulates the STING-dependent response is still being investigated.
iupac name: 4-[(2-chloro-6-fluorophenyl)methyl]-N-(furan-2-ylmethyl)-3-oxo-3,4-dihydro-2H-1,4-benzothiazine-6-carboxamide
approved: f
ligand name: G10 [PMID: 26646986]
type: SyntheticOrganicLigand

compound 13 [Chen et al., 2016]
in ch i key: RQVLGMREYUFLPQ-UHFFFAOYSA-N
in ch i: InChI=1S/C27H24N8O/c1-17-12-18-8-9-19(32-27-29-11-10-25(28-2)33-27)13-23(18)35(17)22-6-4-5-7-24(22)36-20-14-21-26(30-15-20)34(3)16-31-21/h4-16H,1-3H3,(H2,28,29,32,33)
comment: Compound 13 is reported as a DOT1L inhibitor, with a novel chemical structure, distinct from that of <Ligand id=7019/> (EPZ-5676) <Reference id=31041/>. Compound 13 acts as a SAM-competitive inhibitor, binding to an induced pocket adjacent to the SAM binding site.
approved: f
ligand name: compound 13 [Chen et al., 2016]
type: SyntheticOrganicLigand

nazartinib
in ch i key: IOMMMLWIABWRKL-WUTDNEBXSA-N
in ch i: InChI=1S/C26H31ClN6O2/c1-18-16-19(12-13-28-18)25(35)30-26-29-22-10-6-9-21(27)24(22)33(26)20-8-4-5-15-32(17-20)23(34)11-7-14-31(2)3/h6-7,9-13,16,20H,4-5,8,14-15,17H2,1-3H3,(H,29,30,35)/b11-7+/t20-/m1/s1
comment: EGF816 is an irreversible and selective inhibitor of EGFRs harbouring gatekeeper T790M, and sensitising L858R mutations, whilst sparing the wild-type receptor (such compounds are termed third generation EGFR tyrosine kinase inhibitors) <Reference id=31436/>. It has been developed to overcome acquired resistance to, and side-effect liabilities of first and second generation EGFR inhibitors in non-small-cell lung cancer (NSCLC). Small-molecule EGFR T790M inhibitors and the development of novel compounds in the discovery pipeline are reviewed by Song et al. (2016) <Reference id=31035/>. EGF816 is claimed in Novartis' patent WO2015085482 <Reference id=31036/>, where it is named (R,E)-N-(7-chloro-l-(l-(4-(dimethylamino)but-2-enoyl)azepan-3-yl)-lH-benzo[d]imidazol-2-yl)-2-methylisonicotinamide, which resolves to the IUPAC name presented here. Preclinical characterisation is reported in <Reference id=31037/>.
iupac name: N-{7-chloro-1-[(3R)-1-[(2E)-4-(dimethylamino)but-2-enoyl]azepan-3-yl]-1H-1,3-benzodiazol-2-yl}-2-methylpyridine-4-carboxamide
synonym: EGF-816
synonym: EGF816
synonym: compound 47 [PMID: 27433829]
approved: f
ligand name: nazartinib
type: SyntheticOrganicLigand

acumapimod
in ch i key: VGUSQKZDZHAAEE-UHFFFAOYSA-N
in ch i: InChI=1S/C22H19N5O2/c1-13-5-6-16(22(29)26-17-7-8-17)10-19(13)27-21(24)18(12-25-27)20(28)15-4-2-3-14(9-15)11-23/h2-6,9-10,12,17H,7-8,24H2,1H3,(H,26,29)
comment: Acumapimod (BCT-197) is an orally active p38 mitogen activated protein kinase inhibitor with potential anti-inflammatory action. This compound is claimed in patent WO2013139809 <Reference id=31033/> and in patent WO2005009973 as EXAMPLE 52 <Reference id=31034/>.
iupac name: 3-[5-amino-4-(3-cyanobenzoyl)pyrazol-1-yl]-N-cyclopropyl-4-methylbenzamide
synonym: BCT 197
synonym: BCT-197
synonym: BCT197
synonym: compound A [WO2013139809]
approved: f
ligand name: acumapimod
type: SyntheticOrganicLigand

phenylarsine oxide
canonical SMILES: O=[As]c1ccccc1
isomeric SMILES: O=[As]c1ccccc1
in ch i key: BQVCCPGCDUSGOE-UHFFFAOYSA-N
in ch i: InChI=1S/C6H5AsO/c8-7-6-4-2-1-3-5-6/h1-5H
comment: PAO inhibits type III PI 4-kinases, whereas it is relatively ineffective against the type II in in vitro kinase assays. Among the type III enzymes, PI4KIIIα is significantly more sensitive to PAO than the type IIIβ form <Reference id=31030/>.
iupac name: arsorosobenzene
xref: CHEMBL477683
synonym: PAO
synonym: phenylarsenoxide
synonym: arzene
synonym: oxophenylarsine
approved: f
ligand name: phenylarsine oxide
type: SyntheticOrganicLigand

olmutinib
in ch i key: FDMQDKQUTRLUBU-UHFFFAOYSA-N
in ch i: InChI=1S/C26H26N6O2S/c1-3-23(33)27-19-5-4-6-21(17-19)34-25-24-22(11-16-35-24)29-26(30-25)28-18-7-9-20(10-8-18)32-14-12-31(2)13-15-32/h3-11,16-17H,1,12-15H2,2H3,(H,27,33)(H,28,29,30)
comment: Olmutinib from Hanmi Pharmaceutical, approved in South Korea for lung cancer, targets mutant epidermal growth factor receptor (EGFR) selectively over wild-type. It is reported as an oral, third-generation EGFR tyrosine kinase inhibitor (binding covalently), however there is no published, peer-reviewed data to confirm this. The potential for using third-generation EGFR inhibitors in EGFR-mutated non-small lung cancer is reviewed by Russo et al. (2017) <Reference id=33730/>. Olmutinib is claimed in patent WO2011162515 <Reference id=31021/>. Full text descriptions and structure images are available in US20130116213 <Reference id=31023/>, where it is identified as Example 1 (N-(3-(2-(4-(4-methylpiperazin-1-yl)phenylamino)thieno[3,2-d]pyrimidin-4-yloxy)phenyl)acrylamide). Note we updated this entry in Nov 2016 with the removal of the incorrect synonyms HM-71224 and LY3337641 which refer to a blinded Hanmi BTK inhibitor <Reference id=31022/>.
iupac name: N-[3-[2-[4-(4-methylpiperazin-1-yl)anilino]thieno[3,2-d]pyrimidin-4-yl]oxyphenyl]prop-2-enamide
synonym: Example 1 [US20130116213]
synonym: HM61713
synonym: BI-1482694
synonym: BI1482694
synonym: HM-61713
approved: t
ligand name: olmutinib
type: SyntheticOrganicLigand

LY2456302
in ch i key: ZHPMYDSXGRRERG-DEOSSOPVSA-N
in ch i: InChI=1S/C26H27FN2O2/c1-17-12-18(2)14-21(13-17)24-4-3-11-29(24)16-19-5-8-22(9-6-19)31-25-10-7-20(26(28)30)15-23(25)27/h5-10,12-15,24H,3-4,11,16H2,1-2H3,(H2,28,30)/t24-/m0/s1
comment: LY2456302 is a potent small molecule, centrally-penetrant, selective antagonist of the κ opioid receptor, with potential antidepressant-like effects <Reference id=31014/>. It is claimed in patent WO2009094260 <Reference id=31013/>.
iupac name: 4-[4-[[(2S)-2-(3,5-dimethylphenyl)pyrrolidin-1-yl]methyl]phenoxy]-3-fluorobenzamide
xref: CHEMBL1921847
synonym: LY-2456302
synonym: JNJ-67953964
synonym: JNJ67953964
synonym: CERC-501
synonym: CERC501
approved: f
ligand name: LY2456302
type: SyntheticOrganicLigand

AC430
in ch i key: DCRWIATZWHLIPN-QGZVFWFLSA-N
in ch i: InChI=1S/C19H16FN5O/c1-11-10-16(25-24-11)22-18-14-4-2-3-5-15(14)21-19(23-18)17(26)12-6-8-13(20)9-7-12/h2-10,17,26H,1H3,(H2,21,22,23,24,25)/t17-/m1/s1
comment: AC430 is an investigational, potent and selective small molecule inhibitor of janus kinase 2 (JAK2) being developed by Ambit (now owned by Daiichi Sankyo) for the treatment of cancer and autoimmune diseases. AC430 is the (R) optical isomer claimed in patent US8703943 <Reference id=30995/>, although the (S) isomer and racemate are also discussed in the patent descriptions.
iupac name: (R)-(4-fluorophenyl)-[4-[(5-methyl-1H-pyrazol-3-yl)amino]quinazolin-2-yl]methanol
synonym: AC-430
synonym: AC 430
approved: f
ligand name: AC430
type: SyntheticOrganicLigand

WZ4002
in ch i key: ITTRLTNMFYIYPA-UHFFFAOYSA-N
in ch i: InChI=1S/C25H27ClN6O3/c1-4-23(33)28-17-6-5-7-19(14-17)35-24-20(26)16-27-25(30-24)29-21-9-8-18(15-22(21)34-3)32-12-10-31(2)11-13-32/h4-9,14-16H,1,10-13H2,2-3H3,(H,28,33)(H,27,29,30)
comment: WZ4002 is a third generation EGFR inhibitor tool compound which potently inhibits the T790M EGFR mutant and suppresses the growth of cells bearing this mutation <Reference id=22983/><Reference id=30994/>.
iupac name: N-[3-[5-chloro-2-[2-methoxy-4-(4-methylpiperazin-1-yl)anilino]pyrimidin-4-yl]oxyphenyl]prop-2-enamide
xref: CHEMBL1229592
approved: f
ligand name: WZ4002
type: SyntheticOrganicLigand

L-ornithine
canonical SMILES: NC(C(=O)O)CCCN
isomeric SMILES: N[C@H](C(=O)O)CCCN
in ch i key: AHLPHDHHMVZTML-BYPYZUCNSA-N
in ch i: InChI=1S/C5H12N2O2/c6-3-1-2-4(7)5(8)9/h4H,1-3,6-7H2,(H,8,9)/t4-/m0/s1
iupac name: (2S)-2,5-diaminopentanoic acid
xref: CHEMBL446143
synonym: OKG
approved: f
ligand name: L-ornithine
type: MetaboliteLigand

zyklophin
in ch i key: UWLIKQFWZOPOAX-HRFULILYSA-N
in ch i: InChI=1S/C65H96N20O13/c1-3-38(2)54-62(97)83-49(60(95)81-45(21-13-29-73-65(70)71)63(98)85-30-14-22-50(85)61(96)79-43(55(67)90)19-10-11-27-66)35-75-51(87)33-48(59(94)80-44(57(92)84-54)20-12-28-72-64(68)69)82-58(93)47(32-39-15-6-4-7-16-39)78-53(89)37-76-52(88)36-77-56(91)46(31-40-23-25-42(86)26-24-40)74-34-41-17-8-5-9-18-41/h4-9,15-18,23-26,38,43-50,54,74,86H,3,10-14,19-22,27-37,66H2,1-2H3,(H2,67,90)(H,75,87)(H,76,88)(H,77,91)(H,78,89)(H,79,96)(H,80,94)(H,81,95)(H,82,93)(H,83,97)(H,84,92)(H4,68,69,72)(H4,70,71,73)/t38?,43-,44-,45-,46-,47-,48-,49-,50-,54-/m0/s1
comment: Zyklophin is a cyclic analogue of dynorphin A-(1−11) with antagonist action selective for the κ opioid receptor. Structure, synthesis and function is described in <Reference id=31012/>, where it is peptide 2. The peptide is brain-penetrant, and has a relatively short duration of action compared to established small-molecule selective KOR antagonists such as <Ligand id=1642/> <Reference id=31065/>.
xref: CHEMBL574568
approved: f
ligand name: zyklophin
type: PeptideLigand

probe 2.1 [PMID: 24187130]
in ch i key: LRJGJDKBKCTWKM-HZUJVAHNSA-N
in ch i: InChI=1S/C24H22F4N2O2/c1-14-9-10-16(13-18(14)24(26,27)28)29-22(31)17-6-4-5-15-11-12-30(23(32)21(15)17)20-8-3-2-7-19(20)25/h2-5,7-10,13,15,17,21H,6,11-12H2,1H3,(H,29,31)/t15-,17-,21+/m0/s1
comment: Probe 2.1 is a biased agonist for the κ opioid receptor (KOR) <Reference id=31010/>. The compound was designed to preferentially bias KOR activation towards G protein signaling with minimal effects on βarrestin2 recruitment and downstream ERK1/2 activation.
iupac name: (4aR,8S,8aR)-2-(2-fluorophenyl)-N-[4-methyl-3-(trifluoromethyl)phenyl]-1-oxo-1,2,3,4,4a,7,8,8a-octahydroisoquinoline-8-carboxamide
approved: f
ligand name: probe 2.1 [PMID: 24187130]
type: SyntheticOrganicLigand

probe 1.1 [PMID: 24187130]
in ch i key: OQJGZGAYSCWFCK-UHFFFAOYSA-N
in ch i: InChI=1S/C21H17F3N4OS/c1-14-7-8-15(11-17(14)21(22,23)24)13-30-20-27-26-19(18-6-2-3-9-25-18)28(20)12-16-5-4-10-29-16/h2-11H,12-13H2,1H3
comment: Probe 1.1 is a biased agonist for the κ opioid receptor <Reference id=31010/>. The compound was designed to preferentially bias KOR activation towards G protein signaling with minimal effects on βarrestin2 recruitment and downstream ERK1/2 activation.
iupac name: 2-[4-(furan-2-ylmethyl)-5-[[4-methyl-3-(trifluoromethyl)phenyl]methylsulfanyl]-1,2,4-triazol-3-yl]pyridine
synonym: KSC-12-192
approved: f
ligand name: probe 1.1 [PMID: 24187130]
type: SyntheticOrganicLigand

compound 3 [PMID: 23134120]
canonical SMILES: Oc1cccc(c1)CCN(CC1CC1)CCc1ccccc1
isomeric SMILES: Oc1cccc(c1)CCN(CC1CC1)CCc1ccccc1
in ch i key: QURAQIGQNZYJHP-UHFFFAOYSA-N
in ch i: InChI=1S/C20H25NO/c22-20-8-4-7-18(15-20)12-14-21(16-19-9-10-19)13-11-17-5-2-1-3-6-17/h1-8,15,19,22H,9-14,16H2
comment: Compound 3 is a partial agonist of the κ opioid receptor <Reference id=31009/>.
iupac name: 3-[2-[cyclopropylmethyl(2-phenylethyl)amino]ethyl]phenol
xref: CHEMBL2180638
synonym: HS6666
approved: f
ligand name: compound 3 [PMID: 23134120]
type: SyntheticOrganicLigand

HS665
canonical SMILES: Oc1cccc(c1)CCN(CC1CCC1)CCc1ccccc1
isomeric SMILES: Oc1cccc(c1)CCN(CC1CCC1)CCc1ccccc1
in ch i key: YNVKFHIWFDRVNY-UHFFFAOYSA-N
in ch i: InChI=1S/C21H27NO/c23-21-11-5-8-19(16-21)13-15-22(17-20-9-4-10-20)14-12-18-6-2-1-3-7-18/h1-3,5-8,11,16,20,23H,4,9-10,12-15,17H2
comment: HS665 is a highly potent and selective κ opioid receptor agonist <Reference id=31009/>.
iupac name: 3-[2-[cyclobutylmethyl(2-phenylethyl)amino]ethyl]phenol
xref: CHEMBL2180639
synonym: compound 4 [PMID: 23134120]
approved: f
ligand name: HS665
type: SyntheticOrganicLigand

compound 51 [Mallinger et al., 2016]
in ch i key: OJIQEAIHEGJBFE-UHFFFAOYSA-N
in ch i: InChI=1S/C23H22N6O2/c1-28-11-16(9-26-28)14-3-5-15(6-4-14)19-10-25-22(24)18-7-8-20(27-21(18)19)23(30)29-12-17(13-29)31-2/h3-11,17H,12-13H2,1-2H3,(H2,24,25)
comment: Compound 51 is a potent and selective CDK8/19 inhibitor <Reference id=30979/>. It is one of the compounds claimed in patent WO2016009076 <Reference id=30980/>. Compound 51 hasa similar inhibitory potency as <Ligand id=8945/>, but is built on a modified chemical scaffold <Reference id=30979/>. This is a type I inhibitor, binding in a DMG-in mode.
iupac name: [5-amino-8-[4-(1-methylpyrazol-4-yl)phenyl]-1,6-naphthyridin-2-yl]-(3-methoxyazetidin-1-yl)methanone
approved: f
ligand name: compound 51 [Mallinger et al., 2016]
type: SyntheticOrganicLigand

L-alanine
canonical SMILES: CC(C(=O)O)N
isomeric SMILES: C[C@@H](C(=O)O)N
in ch i key: QNAYBMKLOCPYGJ-REOHCLBHSA-N
in ch i: InChI=1S/C3H7NO2/c1-2(4)3(5)6/h2H,4H2,1H3,(H,5,6)/t2-/m0/s1
iupac name: (2S)-2-aminopropanoic acid
xref: CHEMBL279597
approved: f
ligand name: L-alanine
type: MetaboliteLigand

pepcan-12
in ch i key: CSDQEWILNKOWRN-WSDCEOHFSA-N
comment: Pepcan-12 (a peptide endocannabinoid) is reported as a negative allosteric modulator of the cannabinoid receptor type 1 (CB1 receptor) <Reference id=31007/>. Pepcan-12 has identical sequence to the α-hemoglobin-derived dodecapeptide RVD-hemopressin (RVDPVNFKLLSH), proposed as a brain-derived endogenous agonist of CB1 receptors <Reference id=31008/>.
approved: f
ligand name: pepcan-12
type: PeptideLigand

CCT245737
in ch i key: YBYYWUUUGCNAHQ-LLVKDONJSA-N
in ch i: InChI=1S/C16H16F3N7O/c17-16(18,19)12-8-25-14(26-15-9-22-10(4-20)5-24-15)3-13(12)23-7-11-6-21-1-2-27-11/h3,5,8-9,11,21H,1-2,6-7H2,(H2,23,24,25,26)/t11-/m1/s1
comment: CCT245737 is a potent, selective and orally available inhibitor of serine-threonine kinase CHK1 <Reference id=31005/>, with preclinical activity in RAS mutant non-small cell lung cancer and Eμ-MYC driven B-cell lymphoma <Reference id=31006/>.
iupac name: 5-[(4-{[(2R)-morpholin-2-ylmethyl]amino}-5-(trifluoromethyl)pyridin-2-yl)amino]pyrazine-2-carbonitrile
synonym: compound 4 [PMID: 27167172]
approved: f
ligand name: CCT245737
type: SyntheticOrganicLigand

eCF506
in ch i key: GMPQGWXPDRNCBL-UHFFFAOYSA-N
in ch i: InChI=1S/C26H38N8O3/c1-26(2,3)37-25(35)30-19-8-7-17(15-20(19)36-6)22-21-23(27)28-16-29-24(21)34(31-22)14-13-33-11-9-18(10-12-33)32(4)5/h7-8,15-16,18H,9-14H2,1-6H3,(H,30,35)(H2,27,28,29)
comment: eCF506 is a potent and selective inhibitor of SRC family kinases, with activity against breast cancer cells in vitro and in vivo. Design and discovery of this compound is reported in <Reference id=31004/>.
iupac name: tert-butyl N-[4-(4-amino-1-{2-[4-(dimethylamino)piperidin-1-yl]ethyl}-1H-pyrazolo[3,4-d]pyrimidin-3-yl)-2-methoxyphenyl]carbamate
synonym: derivative 11a [PMID: 27115835]
approved: f
ligand name: eCF506
type: SyntheticOrganicLigand

clofazimine
in ch i key: WDQPAMHFFCXSNU-UHFFFAOYSA-N
in ch i: InChI=1S/C27H22Cl2N4/c1-17(2)30-24-16-27-25(15-23(24)31-20-11-7-18(28)8-12-20)32-22-5-3-4-6-26(22)33(27)21-13-9-19(29)10-14-21/h3-17,31H,1-2H3
comment: Clofazimine is a phenazine dye with anti-mycobacterial action (possibly via DNA binding) but is no longer perscribed in the US. It also has anti-inflammatory activities. State-dependent block of Kv1.3 channels by clofazimine offers therapeutic potential for selective immunosuppression in the context of autoimmune diseases in which Kv1.3-expressing T cells play a significant role <Reference id=31003/>. SARS-CoV-2: A report in Nature has identified that clofazimine has anti-coronavirus activity, and that this is synergistic with the antiviral activity of <Ligand id=10715/> <Reference id=41924/>. The drug was found to inhibit viral spike-mediated cell fusion and viral helicase activity in vitro, which translated to reduced pulmonary viral load, gut viral shedding and inflammation in an in vivo infection model. The authors suggest that their data supports the use of clofazimine in an outpatient setting for those infected with SARS-CoV-2, or for hospitalised COVID-19 patients if combined with remdesivir. Based on this evidence it is planned to progress clofazimine + remdesivir directly into Phase 2 clinical trial. A trial of clofazimine + interferon-1β is already underway.
iupac name: N,5-bis(4-chlorophenyl)-3-propan-2-yliminophenazin-2-amine
xref: CHEMBL1292
synonym: Lamprene®
approved: t
ligand name: clofazimine
type: SyntheticOrganicLigand

bihelical apoA-I mimetic peptide 5A
in ch i key: FOIYDQXBMQZAML-GNGNDROBSA-N
comment: The initial 2008 study looked at the effect of asymmetry in the lipid affinity of amphipathic helices in bihelical apoA-I mimetic peptides. The 5A sequence was able to solubilize phospholipid vesicles and stimulated cholesterol and phospholipid efflux by the ABCA1 transporter with high specificity <Reference id=31000/>. A later 2010 study showed that, like apoA-I, the 5A peptide inhibits acute inflammation and oxidative stress in rabbit carotids and human coronary artery endothelial cells. In vitro, the 5A peptide exerts these beneficial effects through interaction with ABCA1 <Reference id=31001/>. Data and peptide analogues related to the latter publication also appeared in patent US8148323 <Reference id=31002/>. A 2016 study indicates 5A peptide ameliorated murine colitis by preventing intestinal monocyte infiltration and activation, implying potential for IBD treatment <Reference id=31626/> (n.b. there are InChIKey missmatch and submission splitting issues with the current PubChem CID 121231406 entry that we hope to resolve).
synonym: 5A peptide
approved: f
ligand name: bihelical apoA-I mimetic peptide 5A
type: PeptideLigand

D-glucose
canonical SMILES: OCC1OC(O)C(C(C1O)O)O
isomeric SMILES: OC[C@H]1OC(O)[C@@H]([C@H]([C@@H]1O)O)O
in ch i key: WQZGKKKJIJFFOK-GASJEMHNSA-N
in ch i: InChI=1S/C6H12O6/c7-1-2-3(8)4(9)5(10)6(11)12-2/h2-11H,1H2/t2-,3-,4+,5-,6?/m1/s1
iupac name: (3R,4S,5S,6R)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol
xref: CHEMBL1222250
approved: f
ligand name: D-glucose
type: MetaboliteLigand

ripretinib
in ch i key: CEFJVGZHQAGLHS-UHFFFAOYSA-N
comment: Ripretinib (DCC-2618) is an orally bioavailable, potent pan-KIT and PDGFRα kinase inhibitor that was developed by Dicephera Pharmaceuticals. It was designed for the treatment of malignancies that are driven by KIT and/or PDGFRα, for example gastrointestinal stromal tumors, glioblastoma multiforme and systemic mastocytosis. Ripretinib has activity across a broad range of resistance mutations in its target kinases, that emerge in response to imatinib treatment. Ripretinib binds to the 'switch pocket' of KIT, a domain that regulates the enzyme's catalytic conformation. Compounds that act in this way are often referred to as switch control inhibitors <Reference id=37677/>. Another example of a switch control inhibitor is <Ligand id=10368/>. The chemical structure shown here matches that supplied to the WHO for the INN, and this is claimed in patent WO2010051373 <Reference id=30993/> as Example 39. Note that some PubChem SIDs are linked to an incorrect structure (as represented in PubChem CID 46208890).
iupac name: 1-[4-bromo-5-[1-ethyl-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]-2-fluorophenyl]-3-phenylurea
synonym: DCC-2618
synonym: DCC2618
synonym: Quinlock®
approved: t
ligand name: ripretinib
type: SyntheticOrganicLigand

altiratinib
in ch i key: GNNDEPIMDAZHRQ-UHFFFAOYSA-N
in ch i: InChI=1S/C26H21F3N4O4/c27-15-3-5-16(6-4-15)31-24(35)26(8-9-26)25(36)32-20-12-19(29)21(13-18(20)28)37-17-7-10-30-22(11-17)33-23(34)14-1-2-14/h3-7,10-14H,1-2,8-9H2,(H,31,35)(H,32,36)(H,30,33,34)
comment: Altiratinib is an oral, selective and potent inhibitor of MET, TIE2, VEGFR2 and TRK kinases, being investigated for its potential anticancer activity. This specific compound is claimed in patent WO2016061231 <Reference id=30992/>, and prior patent submissions. A drug repurposing screen has identified altiratinib as a potential antiprotozoal agent <Reference id=44007/>. The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
iupac name: 1-N'-[4-[2-(cyclopropanecarbonylamino)pyridin-4-yl]oxy-2,5-difluorophenyl]-1-N-(4-fluorophenyl)cyclopropane-1,1-dicarboxamide
xref: CHEMBL3545365
synonym: DCC-270
synonym: DP-5164
synonym: DCC-2701
approved: f
ligand name: altiratinib
type: SyntheticOrganicLigand

rebastinib
in ch i key: WVXNSAVVKYZVOE-UHFFFAOYSA-N
in ch i: InChI=1S/C30H28FN7O3/c1-30(2,3)26-17-27(38(37-26)19-7-9-23-18(14-19)6-5-12-33-23)36-29(40)35-24-10-8-20(15-22(24)31)41-21-11-13-34-25(16-21)28(39)32-4/h5-17H,1-4H3,(H,32,39)(H2,35,36,40)
comment: Rebastinib (DCC-2036) is an investigational orally administered kinase inhibitor, with activity against FLT3-ITD, TIE2, KDR, LYN, BCR-ABL and TRKA kinases. Yes1 inhibition is reported in <Reference id=30991/>. This compound has been termed a switch-control inhibitor as it binds to residues Arg386/Glu282 which ABL1 uses to switch between inactive and active conformations <Reference id=30987/><Reference id=30988/>. Rebastinib inhibits native and phosphphorylated ABL by inducing a type II inactive conformation <Reference id=30987/>. It is one of the compounds claimed in patent WO2008046003 <Reference id=30990/> and subsequent related patent applications. Rebastinib appears to be Example 1, whilst acknowledging the limitations and complexities applied in compound naming and structure provision in the patent document.
iupac name: 4-[4-[(5-tert-butyl-2-quinolin-6-ylpyrazol-3-yl)carbamoylamino]-3-fluorophenoxy]-N-methylpyridine-2-carboxamide
xref: CHEMBL1738757
synonym: DCC-2036
synonym: DCC 2036
synonym: DP-1919
approved: f
ligand name: rebastinib
type: SyntheticOrganicLigand

compound 20 [Bergeron et al., 2016]
in ch i key: LVIYMOOJJGCMCP-KRWDZBQOSA-N
in ch i: InChI=1S/C22H28F3N7O2/c1-26-20-27-6-4-19(30-20)32-7-5-17(14-32)29-21(33)28-16-3-2-15(18(12-16)22(23,24)25)13-31-8-10-34-11-9-31/h2-4,6,12,17H,5,7-11,13-14H2,1H3,(H,26,27,30)(H2,28,29,33)/t17-/m0/s1
comment: Compound 20 is a type II inhibitor (binds in a DMG-out mode) of CDK8, with an improved selectivity profile compared to <Ligand id=5711/> <Reference id=30983/>. It is one of the compounds claimed in patent WO2015049325 <Reference id=30984/>.
iupac name: 1-[(3S)-1-[2-(methylamino)pyrimidin-4-yl]pyrrolidin-3-yl]-3-[4-(morpholin-4-ylmethyl)-3-(trifluoromethyl)phenyl]urea
approved: f
ligand name: compound 20 [Bergeron et al., 2016]
type: SyntheticOrganicLigand

compound 34h [PMID: 27055065]
in ch i key: XTJZKALDRPVFSN-HNNXBMFYSA-N
in ch i: InChI=1S/C24H29N7O/c1-15(24(2,3)4)28-22-21-17(9-10-25-22)12-26-23(30-21)29-19-8-7-16(11-20(19)32-6)18-13-27-31(5)14-18/h7-15H,1-6H3,(H,25,28)(H,26,29,30)/t15-/m0/s1
comment: Compound 34h is an inhibitor of TTK protein kinase (a.k.a. MSP1), active in vivo and with satisfactory pharmacokinetics in rodents <Reference id=30971/>. It is one of the compounds claimed in patent WO2014037750 <Reference id=30972/> (example 77; (S)-N8-(3,3-dimethylbutan-2-yl)-N2-(2-methoxy-4-(1 -methyl-1 H-pyrazol-4- yl)phenyl)pyrido[3,4-d]pyrimidine-2,8-diamine).
iupac name: N8-[(2S)-3,3-dimethylbutan-2-yl]-N2-[2-methoxy-4-(1-methyl-1H-pyrazol-4-yl)phenyl]pyrido[3,4-d]pyrimidine-2,8-diamine
synonym: example 77 [WO2014037750]
approved: f
ligand name: compound 34h [PMID: 27055065]
type: SyntheticOrganicLigand

NCGC 84
canonical SMILES: Cc1n(CC=Cc2ccccc2)c2[n+](c1P(=S)(c1ccccc1)c1ccccc1)cccc2
isomeric SMILES: Cc1n(C/C=C/c2ccccc2)c2[n+](c1P(=S)(c1ccccc1)c1ccccc1)cccc2
in ch i key: VSWYSDPXUHVQCG-DTQAZKPQSA-N
in ch i: InChI=1S/C29H26N2PS/c1-24-29(32(33,26-17-7-3-8-18-26)27-19-9-4-10-20-27)31-22-12-11-21-28(31)30(24)23-13-16-25-14-5-2-6-15-25/h2-22H,23H2,1H3/q+1/b16-13+
comment: NCGC 84 is a competitive, selective, and brain penetrant NPS receptor antagonist <Reference id=30969/>. We show the parent molecule, which is used experimentally as the bromide (PubChem CID 46930969).
xref: CHEMBL1474387
synonym: ML 154
synonym: NCGC 00185684
synonym: NCGC00185684
approved: f
ligand name: NCGC 84
type: SyntheticOrganicLigand

compound C10 [PMID: 24297249]
canonical SMILES: Clc1ccc(cc1)C(c1ccccc1)N1CCNCC1
isomeric SMILES: Clc1ccc(cc1)C(c1ccccc1)N1CCNCC1
in ch i key: UZKBSZSTDQSMDR-UHFFFAOYSA-N
in ch i: InChI=1S/C17H19ClN2/c18-16-8-6-15(7-9-16)17(14-4-2-1-3-5-14)20-12-10-19-11-13-20/h1-9,17,19H,10-13H2
comment: Partially selective GC-B (NPR-B) antagonist that mediates a strong reduction of the maximum cGMP production and no changes of the EC50 values for CNP
iupac name: 1-[(4-chlorophenyl)-phenylmethyl]piperazine
approved: f
ligand name: compound C10 [PMID: 24297249]
type: SyntheticOrganicLigand

BMS-986124
in ch i key: PMPBBWPDHSHENJ-UHFFFAOYSA-N
comment: BMS-986124 is a silent (or neutral) allosteric modulator (SAM) of the μ opioid receptor <Reference id=28284/>. It is one of the compounds claimed in patent WO2014107344 <Reference id=30949/>.
iupac name: 2-(4-bromo-2-methoxyphenyl)-3-(4-chlorobenzenesulfonyl)-1,3-thiazolidine
approved: f
ligand name: BMS-986124
type: SyntheticOrganicLigand

BMS-986123
in ch i key: AXAIHSGKCYUSAN-UHFFFAOYSA-N
in ch i: InChI=1S/C17H19N2O5S2/c1-12-3-6-14(7-4-12)26(22,23)18-9-10-25-17(18)13-5-8-16(24-2)15(11-13)19(20)21/h3-8,11,17,20H,9-10H2,1-2H3
comment: BMS-986123 is a silent (or neutral) allosteric modulator (SAM) of the μ opioid receptor <Reference id=28284/>. It is one of the compounds claimed in patent WO2014107344 <Reference id=30949/>.
iupac name: [hydroxy({2-methoxy-5-[3-(4-methylbenzenesulfonyl)-1,3-thiazolidin-2-yl]phenyl})imino]-λ1-oxidanyl
approved: f
ligand name: BMS-986123
type: SyntheticOrganicLigand

BMS-986122
in ch i key: PNGJPVDGZNPZHY-UHFFFAOYSA-N
comment: BMS-986122 is a positive allosteric modulator (PAM) of the μ opioid receptor <Reference id=28284/>. It is one of the compounds claimed in patent WO2014107344 <Reference id=30949/>. BMS-986122 is built on a chemical scaffold representing a new chemotype for μ receptor PAMs <Reference id=30959/>.
iupac name: 2-(3-bromo-4-methoxyphenyl)-3-(4-chlorophenyl)sulfonyl-1,3-thiazolidine
approved: f
ligand name: BMS-986122
type: SyntheticOrganicLigand

BMS-986121
in ch i key: XUVKOFBHMYDXMJ-UHFFFAOYSA-N
comment: BMS-986121 is a positive allosteric modulator (PAM) of the μ opioid receptor <Reference id=28284/>. It is one of the compounds claimed in patent WO2014107344 <Reference id=30949/>. BMS-986121 is built on a chemical scaffold representing a new chemotype for μ receptor PAMs <Reference id=30959/>.
iupac name: [(4-{2-[(2,6-dichlorophenyl)amino]-1,3-thiazol-4-yl}phenyl)(hydroxy)imino]-λ1-oxidanyl
approved: f
ligand name: BMS-986121
type: SyntheticOrganicLigand

ogerin
canonical SMILES: OCc1ccccc1c1nc(NCc2ccccc2)nc(n1)N
isomeric SMILES: OCc1ccccc1c1nc(NCc2ccccc2)nc(n1)N
in ch i key: MDGIEDNDSFMSLP-UHFFFAOYSA-N
in ch i: InChI=1S/C17H17N5O/c18-16-20-15(14-9-5-4-8-13(14)11-23)21-17(22-16)19-10-12-6-2-1-3-7-12/h1-9,23H,10-11H2,(H3,18,19,20,21,22)
comment: In March 2016 ogerin was reported and named as a selective GPR68 positive allosteric modulator (PAM) <Reference id=30945/>. It binds to the same allosteric binding site on GPR68 as <Ligand id=5884/>. Ogerin potentiates proton activity in GPR68-mediated Gs-cAMP production via increasing both proton affinity (α-cooperativity) and efficacy (β-cooperativity).
iupac name: [2-[4-amino-6-(benzylamino)-1,3,5-triazin-2-yl]phenyl]methanol
synonym: ZINC67740571
approved: f
ligand name: ogerin
type: SyntheticOrganicLigand

(2R,6R) 6-hydroxynorketamine
canonical SMILES: OC1CCCC(C1=O)(N)c1ccccc1Cl
isomeric SMILES: O[C@@H]1CCC[C@@](C1=O)(N)c1ccccc1Cl
in ch i key: CFBVGSWSOJBYGC-ZYHUDNBSSA-N
in ch i: InChI=1S/C12H14ClNO2/c13-9-5-2-1-4-8(9)12(14)7-3-6-10(15)11(12)16/h1-2,4-5,10,15H,3,6-7,14H2/t10-,12-/m1/s1
comment: A recent (April 2016) report <Reference id=30943/> shows that the metabolism of racemic <Ligand id=4233/> to hydroxynorketamine (HNK) is essential for its antidepressant effects, and that these reside in this entry as the (2R,6R)-HNK enantiomer. In mice these actions are independent of NMDAR inhibition and lack ketamine-related side effects. The (flat) rendering of HNK is PubChem CID 133669. The (2S,6S)-HNK is represented as PubChem CID 71519584 but this showed a decreased antidepressant effect compared to (2R,6R)-HNK.
iupac name: (2R,6R)-2-amino-2-(2-chlorophenyl)-6-hydroxycyclohexan-1-one
synonym: (2R,6R)HNK
approved: f
ligand name: (2R,6R) 6-hydroxynorketamine
type: SyntheticOrganicLigand

arketamine
canonical SMILES: CNC1(CCCCC1=O)c1ccccc1Cl
isomeric SMILES: CN[C@]1(CCCCC1=O)c1ccccc1Cl
in ch i key: YQEZLKZALYSWHR-CYBMUJFWSA-N
in ch i: InChI=1S/C13H16ClNO/c1-15-13(9-5-4-8-12(13)16)10-6-2-3-7-11(10)14/h2-3,6-7,15H,4-5,8-9H2,1H3/t13-/m1/s1
comment: This is the less active (R) isomer from the approved drug racemate of <Ligand id=4233/>.
iupac name: (2R)-2-(2-chlorophenyl)-2-methylaminocyclohexan-1-one
xref: CHEMBL467505
synonym: (S) Ketamine
approved: f
ligand name: arketamine
type: SyntheticOrganicLigand

esketamine
canonical SMILES: CNC1(CCCCC1=O)c1ccccc1Cl
isomeric SMILES: CN[C@@]1(CCCCC1=O)c1ccccc1Cl
in ch i key: YQEZLKZALYSWHR-ZDUSSCGKSA-N
in ch i: InChI=1S/C13H16ClNO/c1-15-13(9-5-4-8-12(13)16)10-6-2-3-7-11(10)14/h2-3,6-7,15H,4-5,8-9H2,1H3/t13-/m0/s1
comment: As the ketamine (S) enatiomer esketamine is twice as potent and has a more medically useful pharmacological action than racemic <Ligand id=4233/>. Part of this advantage arises from inhibition of dopamine transporters.
iupac name: (2S)-2-(2-chlorophenyl)-2-methylaminocyclohexan-1-one
xref: CHEMBL395091
synonym: Spravato®
synonym: (S)-Ketamine
approved: t
ligand name: esketamine
type: SyntheticOrganicLigand

crisaborole
canonical SMILES: N#Cc1ccc(cc1)Oc1ccc2c(c1)COB2O
isomeric SMILES: N#Cc1ccc(cc1)Oc1ccc2c(c1)COB2O
in ch i key: USZAGAREISWJDP-UHFFFAOYSA-N
in ch i: InChI=1S/C14H10BNO3/c16-8-10-1-3-12(4-2-10)19-13-5-6-14-11(7-13)9-18-15(14)17/h1-7,17H,9H2
comment: Crisaborole is a non-steroidal phosphodiesterase-4 (PDE4) inhibitor acting primarily against the PDE4B isozyme <Reference id=30942/>. It was developed by Anacor Pharmaceuticals for its potential anti-inflammatory action in skin conditions such as psoriasis and atopic dermatitis.
iupac name: 4-[(1-hydroxy-3H-2,1-benzoxaborol-5-yl)oxy]benzonitrile
xref: CHEMBL484785
synonym: AN2728
synonym: AN 2728
synonym: compound 5b [PMID: 19303290]
synonym: Staquis®
synonym: Eucrisa®
approved: t
ligand name: crisaborole
type: SyntheticOrganicLigand

naldemedine
in ch i key: AXQACEQYCPKDMV-RZAWKFBISA-N
in ch i: InChI=1S/C32H34N4O6/c1-30(2,29-33-27(35-42-29)18-6-4-3-5-7-18)34-28(39)20-15-32(40)22-14-19-10-11-21(37)25-23(19)31(32,26(41-25)24(20)38)12-13-36(22)16-17-8-9-17/h3-7,10-11,17,22,26,37-38,40H,8-9,12-16H2,1-2H3,(H,34,39)/t22-,26+,31+,32-/m1/s1
comment: Naldemedine (S-297995) is a dual μ/δ opioid receptor antagonist, designed to act peripherally (peripherally acting mu-opioid receptor antagonist or PAMORA) <Reference id=37556/>. It is used clinically for its ability to counteract opioid agonist-induced adverse effects such as constipation, nausea, and vomiting. Naldemedine was developed by Shionogi Inc. It is the compound claimed in patent WO2013172297 with formula IA (17-(cyclopropylmethyl)-6,7-didehydro-4,5α-epoxy-3,6,14-trihydroxy-N-[2-(3-phenyl-1,2,4-oxadiazol-5-yl)propan-2-yl]morphinan-7-carboxamide 4-methylbenzenesulfonic acid) <Reference id=30940/>.
iupac name: (4R,4aS,7aR,12bS)-3-(cyclopropylmethyl)-4a,7,9-trihydroxy-N-[2-(3-phenyl-1,2,4-oxadiazol-5-yl)propan-2-yl]-1,2,4,5,7a,13-hexahydro-4,12-methanobenzofuro[3,2-e]isoquinoline-6-carboxamide
xref: CHEMBL2105755
synonym: S-297995
synonym: S-297,995
synonym: compound 9k [PMID: 30446313]
approved: t
ligand name: naldemedine
type: SyntheticOrganicLigand

TUG-905
in ch i key: ODIHLEYTPVYAPY-UHFFFAOYSA-N
in ch i: InChI=1S/C27H30FNO5S/c1-19-15-24(34-13-4-14-35(2,32)33)10-11-25(19)22-6-3-5-20(16-22)18-29-23-9-7-21(26(28)17-23)8-12-27(30)31/h3,5-7,9-11,15-17,29H,4,8,12-14,18H2,1-2H3,(H,30,31)
comment: TUG-905 is a benzylamine agonist of the free fatty acid receptor 1 (FFA1). It is potent and selective in action <Reference id=30937/>. The mesylpropoxy group on the molecule improves ADME properties, likely by reducing lipophilicity.
iupac name: 3-{2-fluoro-4-[({3-[4-(3-methanesulfonylpropoxy)-2-methylphenyl]phenyl}methyl)amino]phenyl}propanoic acid
xref: CHEMBL2164242
synonym: agonist 13 [PMID: 22724451]
approved: f
ligand name: TUG-905
type: SyntheticOrganicLigand

compound 4 [PMID: 27074625]
in ch i key: BNXVSBVQPRGKJS-UHFFFAOYSA-N
in ch i: InChI=1S/C34H34FN4O7/c1-22-17-26(45-16-15-44-14-13-36-30-10-11-31(39(42)43)34-33(30)37-21-38-34)8-9-28(22)25-4-2-3-23(18-25)20-46-27-7-5-24(29(35)19-27)6-12-32(40)41/h2-5,7-11,17-19,36,42H,6,12-16,20-21H2,1H3,(H,40,41)
comment: Compound 4 is a potent and selective fluorescent tracer for the free fatty acid receptor 1 (FFA1) <Reference id=30936/>. It incorporates the nitrobenzoxadiazole (NBD) fluorophore into a structure based on the FFA1 selective agonist, <Ligand id=9149/>. Compound 4 binds competitively with selected synthetic FFA1 agonists, providing a useful tool compound for FFA1 kinetic studies and high throughput binding studies.
iupac name: 3-fluorophenoxymethyl]phenyl}-3-methylphenoxy)ethoxy]ethyl}amino)-2H-1,3-benzodiazol-4-yl](hydroxy)amino}oxidanyl
approved: f
ligand name: compound 4 [PMID: 27074625]
type: SyntheticOrganicLigand

compound 14j [PMID: 27050842]
canonical SMILES: CNCCCc1cncc(c1)CCc1cc(C)cc(n1)N
isomeric SMILES: CNCCCc1cncc(c1)CCc1cc(C)cc(n1)N
in ch i key: YUXWMCKGSHXUGW-UHFFFAOYSA-N
in ch i: InChI=1S/C17H24N4/c1-13-8-16(21-17(18)9-13)6-5-15-10-14(11-20-12-15)4-3-7-19-2/h8-12,19H,3-7H2,1-2H3,(H2,18,21)
comment: Compound 14j is a potent and selective inhibitor of neuronal nitric oxide synthase (nNOS) <Reference id=30933/>.
iupac name: 4-methyl-6-(2-{5-[3-(methylamino)propyl]pyridin-3-yl}ethyl)pyridin-2-amine
approved: f
ligand name: compound 14j [PMID: 27050842]
type: SyntheticOrganicLigand

BI-7273
in ch i key: RBUYFHLQNPJMQM-UHFFFAOYSA-N
in ch i: InChI=1S/C20H23N3O3/c1-22(2)11-17-18(25-4)8-13(9-19(17)26-5)16-12-23(3)20(24)15-10-21-7-6-14(15)16/h6-10,12H,11H2,1-5H3
comment: BI-7273 (compound 1 in PMID: 26914985}, is a selective BRD9 inhibitor tool compound <Reference id=30932/>.
iupac name: 4-[4-[(dimethylamino)methyl]-3,5-dimethoxyphenyl]-2-methyl-2,7-naphthyridin-1-one
approved: f
ligand name: BI-7273
type: SyntheticOrganicLigand

compound 74a [PMID: 27077528]
in ch i key: CWNBNHVIRBCANH-RLLQIKCJSA-N
in ch i: InChI=1S/C20H26N2O2/c1-18(2,3)14-8-10-22-16(11-14)20(12-19(4,24)13-20)17(23)15-7-5-6-9-21-15/h5-11,17,23-24H,12-13H2,1-4H3/t17-,19-,20+/m1/s1
comment: Compound 74a is reported as an antaginist of transient receptor potential vanilloid 3 (TRPV3), optimised for pharmacological, physicochemical, and ADME properties <Reference id=30931/>. This represents a potent and selective tool compound for TRPV3 studies.
iupac name: (1R,3r)-3-(4-tert-butylpyridin-2-yl)-3-[(S)-hydroxy(pyridin-2-yl)methyl]-1-methylcyclobutan-1-ol
approved: f
ligand name: compound 74a [PMID: 27077528]
type: SyntheticOrganicLigand

example 2 [WO2013054185]
in ch i key: BSWOIMAAUKKRAB-UHFFFAOYSA-N
in ch i: InChI=1S/C24H23FN4OS/c25-18-7-5-16(6-8-18)13-21-19-15-29(12-11-17(19)14-26-28-21)24(30)10-9-23-27-20-3-1-2-4-22(20)31-23/h1-8,14,17,19H,9-13,15H2
comment: Example 2 is an autotaxin inhibitor developed by Pfizer, and claimed in patent WO2013054185 <Reference id=30930/>.
iupac name: 6-[3-(1,3-benzothiazol-2-yl)propanoyl]-4-(4-fluorobenzyl)-5,6,7,8-tetrahydropyrido-[4,3-d] pyrimidine
synonym: compound 26 [PMID: 26745766]
approved: f
ligand name: example 2 [WO2013054185]
type: SyntheticOrganicLigand

example 1.11 [WO2014139978]
in ch i key: PCBOWMZAEDDKNH-HOTGVXAUSA-N
comment: Example 1.11 from patent WO2014139978 <Reference id=30929/>, which claims a series of autotaxin inhibitor compounds developed by Hoffmann-La Roche.
iupac name: [4-(trifluoromethoxy)phenyl]methyl (3aS,6aS)-2-(3-fluoro-4-sulfamoylbenzoyl)-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylate
approved: f
ligand name: example 1.11 [WO2014139978]
type: SyntheticOrganicLigand

PF-8380
in ch i key: JMSUDQYHPSNBSN-UHFFFAOYSA-N
comment: PF-8380 is reported as a novel autotaxin inhibitor <Reference id=37629/> for use as a tool compound for investigating the in vivo role of autotaxin and LPA in inflammation and in cancer <Reference id=37629/><Reference id=30924/>. An ATX inhibitor compound named PF-8380 is claimed in patent WO2011151461 <Reference id=30928/>, but this has a different chemical structure from the entity we depict here and whch was disclosed in St-Coeur et al.'s primary publication <Reference id=37629/>.
xref: CHEMBL3186509
synonym: compound 21 [PMID: 26745766]
synonym: PF8380
synonym: compound 4 [PMID: 23300119]
approved: f
ligand name: PF-8380
type: SyntheticOrganicLigand

PKUMDL_MH_1001
isomeric SMILES: CN1CCN(CC1)CC(=O)N1N=C2C(C1c1ccccc1)CCC/C/2=C/c1ccccc1
in ch i key: GEMFAWUXUVGGTE-FCDQGJHFSA-N
in ch i: InChI=1S/C27H32N4O/c1-29-15-17-30(18-16-29)20-25(32)31-27(22-11-6-3-7-12-22)24-14-8-13-23(26(24)28-31)19-21-9-4-2-5-10-21/h2-7,9-12,19,24,27H,8,13-18,20H2,1H3/b23-19+
comment: Computational approaches discovered a previously unknown allosteric site on 15-lipoxygenase (15-LOX). PKUMDL_MH_1001 is reported as a positive allosteric modulator acting at this novel site <Reference id=30923/>. PKUMDL_MH_1001 increases levels of 15-LOX products and reduces production of pro-inflammatory mediators in human whole blood assays. The structure specified in 'supplementary data' <Reference id=30923/> has 2 unresolved stereo centres and there are 9 same connectivity records in PubChem. This compound has potential to drive inflammation resolution by shifting the arachidonic acid metabolic pathway to the production of 15-LOX products such as lipoxins, and inhibiting production of pro-inflammatory mediators such as leukotrienes and prostaglandins.
iupac name: 2-(4-methylpiperazin-1-yl)-1-[(7E)-3-phenyl-7-(phenylmethylidene)-3,3a,4,5,6,7-hexahydro-2H-indazol-2-yl]ethan-1-one
approved: f
ligand name: PKUMDL_MH_1001
type: SyntheticOrganicLigand

nabilone
in ch i key: GECBBEABIDMGGL-UHFFFAOYSA-N
in ch i: InChI=1S/C24H36O3/c1-6-7-8-9-12-23(2,3)16-13-20(26)22-18-15-17(25)10-11-19(18)24(4,5)27-21(22)14-16/h13-14,18-19,26H,6-12,15H2,1-5H3
comment: Nabilone is a synthetic cannabinoid, used as an anti-emetic drug. It is a mixture of enantiomers. We show the 'flat' molecule with no specified stereochemistry to represent the mixture.
iupac name: 1-hydroxy-6,6-dimethyl-3-(2-methyloctan-2-yl)-7,8,10,10a-tetrahydro-6aH-benzo[c]chromen-9-one
xref: CHEMBL2218896
synonym: Cesamet®
synonym: LY 109514
synonym: LY-109514
approved: t
ligand name: nabilone
type: SyntheticOrganicLigand

PEN
in ch i key: FQPFUCOMMICWOE-CPPASMBOSA-N
comment: Neuroendocrine peptide PEN is one of the peptide fragments cleaved from the pro-peptide ProSAAS (encoded by the Pcsk1n gene). Mouse PEN comprises amino acids 219-240 of the pro-protein. PEN activity in the brain is implicated in the regulation of feeding. PEN has been identified as an endogenous ligand for GPR83 <Reference id=30921/>. It is suggested that the PEN-GPR83 and <Ligand id=6704/>-GPR171 ligand-receptor systems may be functionally coupled as a mechanism to regulate feeding.
approved: f
ligand name: PEN
type: PeptideLigand

neoceptin-4
in ch i key: NRHPXDROGIVILZ-XMMPIXPASA-N
in ch i: InChI=1S/C28H32N2O5/c1-28(2,3)35-27(33)24(16-11-19-7-5-4-6-8-19)30-26(32)21-12-15-23(29)25(17-21)34-18-20-9-13-22(31)14-10-20/h4-10,12-15,17,24,31H,11,16,18,29H2,1-3H3,(H,30,32)/t24-/m1/s1
comment: Neoceptin-4 is a synthetic Toll-like receptor 4 (TLR4) agonist <Reference id=30919/>. It bears no structural similarity with the endogenous ligand for TLR4, <Ligand id=5019/>. This is one of the compounds claimed in patent WO2014131023 <Reference id=30920/> in which the neoceptin's action as an immune system adjuvant is claimed. Neoceptins are claimed for their ability to elicit an immune response via the TLR4, without the toxicity exhibited by LPS.
iupac name: tert-butyl (2R)-2-({4-amino-3-[(4-hydroxyphenyl)methoxy]phenyl}formamido)-4-phenylbutanoate
approved: f
ligand name: neoceptin-4
type: SyntheticOrganicLigand

neoceptin-3
in ch i key: OACODUCFPHHCIH-SANMLTNESA-N
in ch i: InChI=1S/C29H34N2O4/c1-29(2,3)35-28(34)26(18-12-20-7-5-4-6-8-20)31-27(33)23-14-17-25(30)22(19-23)13-9-21-10-15-24(32)16-11-21/h4-8,10-11,14-17,19,26,32H,9,12-13,18,30H2,1-3H3,(H,31,33)/t26-/m0/s1
comment: Neoceptin-3 is a synthetic molecular Toll-like receptor 4 (TLR4) agonist mimetic <Reference id=30919/>. It bears no structural similarity with the endogenous ligand for TLR4, <Ligand id=5019/>, and in fact the biologically relevant molecular target for neoseptin-3 is the TLR4/MD-2 (LY96) complex <Reference id=30918/>. This is one of the compounds claimed in patent WO2014131023 <Reference id=30920/> in which the compound's action as an immune system adjuvant is claimed. Neoceptin-3 is claimed for its ability to elicit an immune response via TLR4, without the toxicity exhibited by LPS <Reference id=30918/>. The S stereoisomer is specified in <Reference id=30918/>. The R stereoisomer is represented by PubChem CID 90371379.
iupac name: tert-butyl (2S)-2-[[4-amino-3-[2-(4-hydroxyphenyl)ethyl]benzoyl]amino]-4-phenylbutanoate
approved: f
ligand name: neoceptin-3
type: SyntheticOrganicLigand

SB-674042
in ch i key: HYBZWVLPALMACV-KRWDZBQOSA-N
in ch i: InChI=1S/C24H21FN4O2S/c1-15-26-21(22(32-15)18-11-5-6-12-19(18)25)24(30)29-13-7-10-17(29)14-20-27-28-23(31-20)16-8-3-2-4-9-16/h2-6,8-9,11-12,17H,7,10,13-14H2,1H3/t17-/m0/s1
comment: SB-674042 is a non-peptide antagonist selective for the orexin 1 receptor (OX1) <Reference id=5601/>. See <Ligand id=1706/> for further ligand binding characteristics. Compare with <Ligand id=2890/>, a non-selective orexin receptor antagonist used clinically.
iupac name: [5-(2-fluorophenyl)-2-methyl-1,3-thiazol-4-yl]-[(2S)-2-[(5-phenyl-1,3,4-oxadiazol-2-yl)methyl]pyrrolidin-1-yl]methanone
xref: CHEMBL2110363
synonym: SB 674042
synonym: SB674042
approved: f
ligand name: SB-674042
type: SyntheticOrganicLigand

MK-0893
in ch i key: DNTVJEMGHBIUMW-IBGZPJMESA-N
comment: MK-0893 is reported as a potent, reversible and competitive antagonist of the glucagon receptor, with anti-type II diabetes potential <Reference id=30913/>. X-ray crystallography shows that MK-0893 in fact binds to an allosteric site outside the seven transmembrane bundle <Reference id=30914/>.
iupac name: 3-[[4-[(1S)-1-[3-(3,5-dichlorophenyl)-5-(6-methoxynaphthalen-2-yl)pyrazol-1-yl]ethyl]benzoyl]amino]propanoic acid
xref: CHEMBL1933349
synonym: MK 0893
synonym: N-[(4-{(1S)-1-[3-(3,5-dichlorophenyl)-5-(6-methoxynaphthalen-2-yl)-1H-pyrazol-1-yl]ethyl}phenyl)carbonyl]-β-alanine
synonym: MK-0893-005
synonym: MK0893
synonym: compound 9m [PMID: 22708876]
approved: f
ligand name: MK-0893
type: SyntheticOrganicLigand

GSK583
in ch i key: XLOGLWKOHPIJLV-UHFFFAOYSA-N
in ch i: InChI=1S/C20H19FN4O2S/c1-20(2,3)28(26,27)13-5-7-16-14(11-13)17(8-9-22-16)23-19-15-10-12(21)4-6-18(15)24-25-19/h4-11H,1-3H3,(H2,22,23,24,25)
comment: GSK583 is a potent and selective next generation inhibitor of receptor interacting serine/threonine kinase 2 (RIP2 kinase) <Reference id=30910/>. It is compound 27 in <Reference id=30910/> and compound 89 claimed in patent WO2011140442 <Reference id=30911/>. GSK583 can be used as a tool compound to investigate the role played by RIP2 kinase in NOD1 and NOD2 mediated pathology.
iupac name: N-(5-fluoro-1H-indazol-3-yl)-6-(2-methylpropane-2-sulfonyl)quinolin-4-amine
synonym: GSK'583
approved: f
ligand name: GSK583
type: SyntheticOrganicLigand

glesatinib
in ch i key: YRCHYHRCBXNYNU-UHFFFAOYSA-N
comment: Glesatinib is an orally available dual MET receptor tyrosine kinase and SMO (Hedgehog pathway) inhibitor <Reference id=42920/><Reference id=42921/><Reference id=42922/>. Negative regulation of the Hedgehog pathway seems to enhance the compound's antiproliferative activity in NSCLC with resistance to type I MET inhibitors.
iupac name: N-[[3-fluoro-4-[2-[5-[(2-methoxyethylamino)methyl]pyridin-2-yl]thieno[3,2-b]pyridin-7-yl]oxyphenyl]carbamothioyl]-2-(4-fluorophenyl)acetamide
xref: CHEMBL3989914
synonym: MGCD 265
synonym: MGCD-265
synonym: MGCD265
synonym: compound 10a [PMID: 18434145]
approved: f
ligand name: glesatinib
type: SyntheticOrganicLigand

PLX8394
in ch i key: YYACLQUDUDXAPA-MRXNPFEDSA-N
comment: PLX8394 is an investigational orally available, next-generation small molecule RAF inhibitor <Reference id=30905/>. It has potential antineoplastic activity. Structurally, PLX8394 is similar to the first-generation BRAF inhibitor <Ligand id=5893/>. PLX8394 inhibits wild-type and mutated forms of BRAF. PLX8394 and compounds like it have been termed 'paradox breakers' as they are designed to inhibit mutant BRAF kinase activity without activating the MAPK pathway in cells bearing upstream activation, as many of the original BRAF inhibitors are prone to do. PLX8394 is one of the compounds claimed in patent WO2014194127 <Reference id=30906/>, although as the images are unavailable or redacted it is impossible to precisely identify the structure in the patent documentation.
iupac name: (R)-N-(3-(5-(2-cyclopropylpyrimidin-5-yl)-1H-pyrrolo[2,3-b]pyridine-3-carbonyl)-2,4-difluorophenyl)-3-fluoropyrrolidine-1-sulfonamide
synonym: PLX-8394
synonym: PLX 8394
approved: f
ligand name: PLX8394
type: SyntheticOrganicLigand

ZM336372
in ch i key: PYEFPDQFAZNXLI-UHFFFAOYSA-N
in ch i: InChI=1S/C23H23N3O3/c1-15-7-10-18(24-23(29)17-5-4-6-19(13-17)26(2)3)14-21(15)25-22(28)16-8-11-20(27)12-9-16/h4-14,27H,1-3H3,(H,24,29)(H,25,28)
comment: ZM336372 is an experimental inhibitor of RAF kinases <Reference id=30904/>.
iupac name: 3-dimethylamino-N-[3-[(4-hydroxybenzoyl)amino]-4-methylphenyl]benzamide
xref: CHEMBL186526
synonym: ZM-336372
synonym: ZM 336372
synonym: compound 1 [PMID: 15454231]
approved: f
ligand name: ZM336372
type: SyntheticOrganicLigand

megestrol
in ch i key: VXIMPSPISRVBPZ-NWUMPJBXSA-N
in ch i: InChI=1S/C22H30O3/c1-13-11-16-17(20(3)8-5-15(24)12-19(13)20)6-9-21(4)18(16)7-10-22(21,25)14(2)23/h11-12,16-18,25H,5-10H2,1-4H3/t16-,17+,18+,20-,21+,22+/m1/s1
comment: Megestrol (commonly administered as the acetate ester: PubChem CID 11683) is a synthetic derivative of the female sex hormone progesterone. It has anti-estrogenic and antineoplastic activity.
iupac name: (8R,9S,10R,13S,14S,17R)-17-acetyl-17-hydroxy-6,10,13-trimethyl-2,8,9,11,12,14,15,16-octahydro-1H-cyclopenta[a]phenanthren-3-one
synonym: Megace®
synonym: Magestin
synonym: megestryl acetate
synonym: Chronopil
approved: t
ligand name: megestrol
type: SyntheticOrganicLigand

BAY-524
in ch i key: LMRCQVHTZUUHFN-UHFFFAOYSA-N
in ch i: InChI=1S/C24H24F2N6O3/c1-5-35-16-10-18(25)17(19(26)11-16)13-32-24(34-4)14(2)21(31-32)23-28-12-20(33-3)22(30-23)29-15-6-8-27-9-7-15/h6-12H,5,13H2,1-4H3,(H,27,28,29,30)
comment: BAY-524 is a Bub1 kinase inhibitor <Reference id=30895/>. This can be used as a tool compound for investigating Bub1 kinase function.
iupac name: 2-[1-[(4-ethoxy-2,6-difluorophenyl)methyl]-5-methoxy-4-methylpyrazol-3-yl]-5-methoxy-N-pyridin-4-ylpyrimidin-4-amine
approved: f
ligand name: BAY-524
type: SyntheticOrganicLigand

BAY-320
in ch i key: WAELFQHBZPHEMW-UHFFFAOYSA-N
in ch i: InChI=1S/C26H26F2N6O2/c1-4-36-18-11-20(27)19(21(28)12-18)14-34-24(16-5-6-16)15(2)23(33-34)26-30-13-22(35-3)25(32-26)31-17-7-9-29-10-8-17/h7-13,16H,4-6,14H2,1-3H3,(H,29,30,31,32)
comment: BAY-320 is a Bub1 kinase inhibitor <Reference id=30895/>. This can be used as a tool compound for investigating Bub1 kinase function.
iupac name: 2-[5-cyclopropyl-1-[(4-ethoxy-2,6-difluorophenyl)methyl]-4-methylpyrazol-3-yl]-5-methoxy-N-pyridin-4-ylpyrimidin-4-amine
approved: f
ligand name: BAY-320
type: SyntheticOrganicLigand

compound 1a [PMID: 25692029]
in ch i key: CWJPVKSBGVPXRD-QMTMVMCOSA-N
in ch i: InChI=1S/C21H27N2O5P/c1-14(21(25)26)23-20(24)19(13-29(27,28)15(2)22)12-16-8-10-18(11-9-16)17-6-4-3-5-7-17/h3-11,14-15,19H,12-13,22H2,1-2H3,(H,23,24)(H,25,26)(H,27,28)/t14-,15+,19+/m0/s1
comment: Active compound formed from prodrug <Ligand id=9090/>.
iupac name: (2S)-2-[[(2S)-2-[[[(1R)-1-aminoethyl]-hydroxyphosphoryl]methyl]-3-(4-phenylphenyl)propanoyl]amino]propanoic acid
approved: f
ligand name: compound 1a [PMID: 25692029]
type: SyntheticOrganicLigand

ACT-335827
in ch i key: HXHOBPVRRPCTLG-SETSBSEESA-N
in ch i: InChI=1S/C31H38N2O5/c1-20(2)32-31(34)30(22-10-8-7-9-11-22)33-15-14-23-18-28(37-5)29(38-6)19-24(23)25(33)16-21-12-13-26(35-3)27(17-21)36-4/h7-13,17-20,25,30H,14-16H2,1-6H3,(H,32,34)/t25-,30+/m0/s1
comment: ACT-335827 is an orally available, brain penetrant, selective antagonist of orexin receptor type 1 (OX1) <Reference id=30883/>. The compound is a useful selective pharmacological tool for in vivo investigations, having reported stress relieving effects in animal models.
iupac name: (2R)-2-[(1S)-1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl]-2-phenyl-N-propan-2-ylacetamide
xref: CHEMBL2413367
synonym: ACT 335827
synonym: compound 9 [PMID: 23589487]
approved: f
ligand name: ACT-335827
type: SyntheticOrganicLigand

LSN2424100
in ch i key: PCDMCECXKAELMI-UHFFFAOYSA-N
in ch i: InChI=1S/C22H18FN3O2S/c23-18-10-12-19(13-11-18)29(27,28)26(16-22-24-14-15-25-22)21-9-5-4-8-20(21)17-6-2-1-3-7-17/h1-15H,16H2,(H,24,25)
comment: LSN2424100 is a potent orexin receptor antagonist (OX2 selective) with potential antidepressant-like action <Reference id=30882/>. Can be used as an experimental probe of OX2 receptor-mediated signaling.
iupac name: 4-fluoro-N-(1H-imidazol-2-ylmethyl)-N-(2-phenylphenyl)benzene-1-sulfonamide
approved: f
ligand name: LSN2424100
type: SyntheticOrganicLigand

pelabresib
in ch i key: GCWIQUVXWZWCLE-INIZCTEOSA-N
in ch i: InChI=1S/C20H16ClN3O2/c1-11-18-14-4-2-3-5-15(14)19(12-6-8-13(21)9-7-12)23-16(10-17(22)25)20(18)26-24-11/h2-9,16H,10H2,1H3,(H2,22,25)/t16-/m0/s1
comment: Pelabresib (CPI-0610) is an investigational BET inhibitor with anti-tumour potential <Reference id=30871/>. BET inhibitors bind to the bromodomains of the bromodomain and extra-terminal motif (BET) proteins BRD2, BRD3, BRD4, and BRDT. This mechanism acts to prevent protein-protein interaction between BET proteins and acetylated histones and transcription factors. The action disrupts chromatin remodeling and inhibits expression of some growth-promoting genes which slows proliferation in susceptible tumours.
iupac name: 2-[(4S)-6-(4-chlorophenyl)-1-methyl-4H-[1,2]oxazolo[5,4-d][2]benzazepin-4-yl]acetamide
synonym: compound 10 [PMID: 26815195]
synonym: CPI0610
synonym: CPI-0610
approved: f
ligand name: pelabresib
type: SyntheticOrganicLigand

mivebresib
in ch i key: RDONXGFGWSSFMY-UHFFFAOYSA-N
comment: Mivebresib (ABBV-075) is a potent orally available BET inhibitor <Reference id=33665/>. BET inhibitors bind to the bromodomains of the bromodomain and extra-terminal motif (BET) proteins BRD2, BRD3, BRD4, and BRDT. This mechanism acts to prevent protein-protein interaction between BET proteins and acetylated histones and transcription factors. The action disrupts chromatin remodeling and inhibits expression of some growth-promoting genes which slows proliferation in susceptible tumours.
iupac name: N-(4-(2,4-difluorophenoxy)-3-(6-methyl-7-oxo-6,7-dihydro-1H-pyrrolo[2,3-c]pyridin-4-yl)phenyl)ethanesulfonamide
synonym: ABBV-075
synonym: ABBV075
synonym: Example 36 [WO2013097601]
approved: f
ligand name: mivebresib
type: SyntheticOrganicLigand

GSK2879552
in ch i key: LRULVYSBRWUVGR-FCHUYYIVSA-N
in ch i: InChI=1S/C23H28N2O2/c26-23(27)20-8-6-18(7-9-20)16-25-12-10-17(11-13-25)15-24-22-14-21(22)19-4-2-1-3-5-19/h1-9,17,21-22,24H,10-16H2,(H,26,27)/t21-,22+/m0/s1
comment: GSK2879552 is an orally available, irreversible inhibitor of lysine specific demethylase 1 (LSD1; officially known as lysine demethylase 1A, KDM1A). It was investigated for potential to modulate epigenetic regulation in cancer, but the programme was terminated due to serious adverse events becoming evident in early trials <Reference id=38347/>. GSK2879552-induced LDS1 inhibition causes expression of proteins indicative of a differentiated immunophenotype. GSK2879552 is Example 26 claimed in patent WO2012135113 <Reference id=30869/>.
iupac name: 4-[[4-[[[(1R,2S)-2-phenylcyclopropyl]amino]methyl]piperidin-1-yl]methyl]benzoic acid
synonym: GSK-2879552
synonym: Example 26 [WO2012135113]
approved: f
ligand name: GSK2879552
type: SyntheticOrganicLigand

compound 27 [PMID: 26938474]
canonical SMILES: O=C(c1sc2c(c1C)c(=O)[nH]cn2)Nc1nncs1
isomeric SMILES: O=C(c1sc2c(c1C)c(=O)[nH]cn2)Nc1nncs1
in ch i key: CDWYKQOLMLZLKK-UHFFFAOYSA-N
in ch i: InChI=1S/C10H7N5O2S2/c1-4-5-7(16)11-2-12-9(5)19-6(4)8(17)14-10-15-13-3-18-10/h2-3H,1H3,(H,11,12,16)(H,14,15,17)
comment: Compound 27 is an inhibitor of branched chain aminotransferase 2 (BCAT2, a.k.a. BCATm) <Reference id=30750/>. GSK identified this molecule in a fragment screening and SAR study to identify BCAT2 inhibitors, which they suggest may have anti-obesity potential.
iupac name: 5-methyl-4-oxo-N-(1,3,4-thiadiazol-2-yl)-3H-thieno[2,3-d]pyrimidine-6-carboxamide
approved: f
ligand name: compound 27 [PMID: 26938474]
type: SyntheticOrganicLigand

CPI-1205
in ch i key: HPODOLXTMDHLLC-QGZVFWFLSA-N
in ch i: InChI=1S/C27H33F3N4O3/c1-16-13-23(37-4)21(25(35)32-16)14-31-26(36)24-18(3)34(22-8-6-5-7-20(22)24)17(2)19-9-11-33(12-10-19)15-27(28,29)30/h5-8,13,17,19H,9-12,14-15H2,1-4H3,(H,31,36)(H,32,35)/t17-/m1/s1
comment: CPI-1205 is an orally available selective inhibitor of the histone lysine methyltransferase EZH2, with potential antineoplastic activity <Reference id=31871/>. The developer is Constellation Pharmaceuticals whose patents WO2012068589 <Reference id=30866/> and more recently, WO2014151142A1 <Reference id=30867/>, claim many compounds for their potential to modulate methylation modifying enzymes. WO2014151142A1 specifically claims inhibition of EZH2, with in vitro IC50 values vs. EZH2 for compounds 100-145 presented in Table 2. See also Garapaty-Ra et al. (2013) <Reference id=30868/> for further examples of EZH2/EZH1 inhibitors developed by Constellation Pharmaceuticals.
iupac name: N-[(4-methoxy-6-methyl-2-oxo-1H-pyridin-3-yl)methyl]-2-methyl-1-[(1R)-1-[1-(2,2,2-trifluoroethyl)piperidin-4-yl]ethyl]indole-3-carboxamide
synonym: CPI 1205
synonym: CPI1205
synonym: compound 13 [PMID: 27739677]
approved: f
ligand name: CPI-1205
type: SyntheticOrganicLigand

compound 8b [PMID: 22408719]
in ch i key: DWYMDWVNEIIEHC-UHFFFAOYSA-N
in ch i: InChI=1S/C31H29N3O4S/c1-20(35)32-24-12-14-25(15-13-24)39-19-23-17-22(11-16-28(23)38-2)30-33-26-9-6-10-27(36)29(26)31(37)34(30)18-21-7-4-3-5-8-21/h3-17,30,33,36H,18-19H2,1-2H3,(H,32,35)
comment: Compound 8b is an agonist of the thyroid stimulating hormone receptor (TSHR) <Reference id=30864/>.
xref: CHEMBL1715624
approved: f
ligand name: compound 8b [PMID: 22408719]
type: SyntheticOrganicLigand

GIV3727
canonical SMILES: CC1CCC(C1(C)C)CCCC(=O)O
isomeric SMILES: CC1CCC(C1(C)C)CCCC(=O)O
in ch i key: LYFXCRCUENNESS-UHFFFAOYSA-N
in ch i: InChI=1S/C12H22O2/c1-9-7-8-10(12(9,2)3)5-4-6-11(13)14/h9-10H,4-8H2,1-3H3,(H,13,14)
comment: GIV3727 is an orthosteric antagonist of the human bitterness receptor TAS2R31 <Reference id=30862/>. It inhibits the receptor's activation by the commonly used artificial sweeteners, <Ligand id=5432/> and acesulfame K. It also antagonises the highly similar TAS2R43 receptor. This is one of the compounds claimed in patent WO2008119196, covering the use of compounds to mask the off-notes that can be detected in consumables containing artificial sweeteners <Reference id=30863/>.
iupac name: 4-(2,2,3-trimethylcyclopentyl)butanoic acid
approved: f
ligand name: GIV3727
type: SyntheticOrganicLigand

6-methoxysakuranetin
canonical SMILES: COc1cc2OC(CC(=O)c2c(c1OC)O)c1ccc(cc1)O
in ch i key: DEOJMRBCCZJDEC-LBPRGKRZSA-N
in ch i: InChI=1S/C17H16O6/c1-21-14-8-13-15(16(20)17(14)22-2)11(19)7-12(23-13)9-3-5-10(18)6-4-9/h3-6,8,12,18,20H,7H2,1-2H3/t12-/m0/s1
comment: 6-methoxysakuranetin is a methoxylated flavanone compound with taste-modifying action. Reported to modify the response to <Ligand id=5432/> at the human bitterness receptor TAS2R31 <Reference id=30861/>.
iupac name: (2S)-5-hydroxy-2-(4-hydroxyphenyl)-6,7-dimethoxy-2,3-dihydrochromen-4-one
xref: CHEMBL210692
synonym: compound 33 [PMID: 21650152]
approved: f
ligand name: 6-methoxysakuranetin
type: NaturalProductLigand

GSK334429
in ch i key: AHHPKVQYHXNBQN-UHFFFAOYSA-N
in ch i: InChI=1S/C20H29F3N4O/c1-15(2)25-8-3-9-27(13-12-25)19(28)16-6-10-26(11-7-16)17-4-5-18(24-14-17)20(21,22)23/h4-5,14-16H,3,6-13H2,1-2H3
comment: GSK334429 is a histamine H3 receptor antagonist.
iupac name: (4-propan-2-yl-1,4-diazepan-1-yl)-[1-[6-(trifluoromethyl)pyridin-3-yl]piperidin-4-yl]methanone
xref: CHEMBL2151157
synonym: GSK 334429
synonym: GSK-334429
approved: f
ligand name: GSK334429
type: SyntheticOrganicLigand

SC-22716
canonical SMILES: C1CCN(C1)CCOc1ccc(cc1)c1ccccc1
isomeric SMILES: C1CCN(C1)CCOc1ccc(cc1)c1ccccc1
in ch i key: PKUGRVAJRGZDJP-UHFFFAOYSA-N
in ch i: InChI=1S/C18H21NO/c1-2-6-16(7-3-1)17-8-10-18(11-9-17)20-15-14-19-12-4-5-13-19/h1-3,6-11H,4-5,12-15H2
comment: SC-22716 is an experimental leukotriene A4 hydrolase inhibitor. It was the primary lead for the SAR study reported in <Reference id=30822/>. SC-22716 acts as a potent, competitive and reversible inhibitor of the hydrolase and peptidase activities of human leukotriene A4 hydrolase.
iupac name: 1-[2-(4-Phenylphenoxy)ethyl]pyrrolidine
xref: CHEMBL119054
synonym: SC 22716
approved: f
ligand name: SC-22716
type: SyntheticOrganicLigand

flortaucipir (18F)
canonical SMILES: Fc1ccc(cn1)c1ccc2c(c1)[nH]c1c2cncc1
isomeric SMILES: [18F]c1ccc(cn1)c1ccc2c(c1)[nH]c1c2cncc1
in ch i key: GETAAWDSFUCLBS-SJPDSGJFSA-N
in ch i: InChI=1S/C16H10FN3/c17-16-4-2-11(8-19-16)10-1-3-12-13-9-18-6-5-14(13)20-15(12)7-10/h1-9,20H/i17-1
comment: Flortaucipir (18F) is an investigational PET imaging agent (diagnostic radiopharmaceutical) designed to visualise tau protein (MAPT; P10636) in Alzheimer's disease brains. Compare with the approved agent, <Ligand id=7344/>, used to visualise β-amyloid.
iupac name: 7-(6-fluoranylpyridin-3-yl)-5H-pyrido[4,3-b]indole
xref: CHEMBL3545253
synonym: Tauvid®
synonym: LY-3191748
synonym: 18F-AV-1451
synonym: [F-18]T807
synonym: flortaucipir F-18
approved: f
ligand name: flortaucipir (18F)
type: SyntheticOrganicLigand

lumateperone
in ch i key: HOIIHACBCFLJET-UHFFFAOYSA-N
in ch i: InChI=1S/C24H28FN3O/c1-26-14-15-28-21-11-13-27(16-20(21)19-4-2-5-22(26)24(19)28)12-3-6-23(29)17-7-9-18(25)10-8-17/h2,4-5,7-10,20-21H,3,6,11-16H2,1H3
comment: Lumateperone (ITI-007) is an antipsychotic, with a novel mechanism of action, making it the first-in class agent of its type <Reference id=38551/><Reference id=38553/>. Note that the approved drug contains lumateperone tosylate (PubChem CID 44241743).
xref: CHEMBL3545045
synonym: Caplyta®
synonym: ITI-007
approved: t
ligand name: lumateperone
type: SyntheticOrganicLigand

methoxamine
canonical SMILES: COc1ccc(c(c1)C(C(N)C)O)OC
isomeric SMILES: COc1ccc(c(c1)C(C(N)C)O)OC
in ch i key: WJAJPNHVVFWKKL-UHFFFAOYSA-N
in ch i: InChI=1S/C11H17NO3/c1-7(12)11(13)9-6-8(14-2)4-5-10(9)15-3/h4-7,11,13H,12H2,1-3H3
comment: Methoxamine is an brain-penetrant α1-adrenoceptor agonist.
iupac name: 2-amino-1-(2,5-dimethoxyphenyl)propan-1-ol
xref: CHEMBL524
synonym: 2,5-dimethoxynorephedrine
synonym: Metossamina
synonym: Metoxamina
synonym: Pseudomethoxamine
synonym: Vasoxine
synonym: Methoxamin
synonym: Vasoxyl
synonym: Methoxamedrine
approved: t
ligand name: methoxamine
type: SyntheticOrganicLigand

zotiraciclib
isomeric SMILES: CN1C/C=C/CCOc2cccc(c2)c2nc(Nc3cc(C1)ccc3)ncc2
in ch i key: VXBAJLGYBMTJCY-NSCUHMNNSA-N
in ch i: InChI=1S/C23H24N4O/c1-27-13-3-2-4-14-28-21-10-6-8-19(16-21)22-11-12-24-23(26-22)25-20-9-5-7-18(15-20)17-27/h2-3,5-12,15-16H,4,13-14,17H2,1H3,(H,24,25,26)/b3-2+
comment: Zotiraciclib (TG02) is an orally active multi-kinase inhibitor, with a unique activity profile against CDKs, JAK2 and FLT3 <Reference id=30803/><Reference id=30804/>. Like <Ligand id=7793/> it is a small molecule macrocycle. TG02 was rationally designed to simultaneously inhibit several key signalling pathways, with the aim of maximising anti-cancer efficacy. It is being investigated for its anti-leukemic potential <Reference id=30805/><Reference id=30806/>. The compound is administered as the citrate salt.
xref: CHEMBL1944698
synonym: TG-02
synonym: SB1317
synonym: SB-1317
synonym: compound 26h [PMID: 22148278]
synonym: TG02
approved: f
ligand name: zotiraciclib
type: SyntheticOrganicLigand

compound 1 [PMID: 24930776]
isomeric SMILES: Nc1ccc(c(c1)N)/N=N/c1ccc2c(c1)c(O)c(c(c2)S(=O)(=O)O)/N=N/c1ccc(c(c1)S(=O)(=O)O)/N=N/c1ccc(cc1N)N
in ch i key: ADRMADAIKSWNOR-GOCYIQQKSA-N
comment: Compound 1 inhibits the co-stimulatory protein-protein interaction between the tumour necrosis factor receptor OX40 and the endogenous OX-40 ligand, by binding to the receptor rather than the ligand <Reference id=30800/>. This interaction is a promising therapeutic target for immunomodulation. Cellular assays indicate that compound 1 has partial agonist activity at OX40. PubChem CID 6817797 respresents an alternative stereochemical structure for this compound.
iupac name: 6-[(Z)-2-(2,4-diaminophenyl)diazen-1-yl]-3-[(E)-2-{4-[(E)-2-(2,4-diaminophenyl)diazen-1-yl]-3-sulfophenyl}diazen-1-yl]-4-hydroxynaphthalene-2-sulfonic acid
synonym: DB36
approved: f
ligand name: compound 1 [PMID: 24930776]
type: SyntheticOrganicLigand

NS-398
canonical SMILES: [O-][N+](=O)c1ccc(c(c1)OC1CCCCC1)NS(=O)(=O)C
isomeric SMILES: [O-][N+](=O)c1ccc(c(c1)OC1CCCCC1)NS(=O)(=O)C
in ch i key: KTDZCOWXCWUPEO-UHFFFAOYSA-N
in ch i: InChI=1S/C13H18N2O5S/c1-21(18,19)14-12-8-7-10(15(16)17)9-13(12)20-11-5-3-2-4-6-11/h7-9,11,14H,2-6H2,1H3
comment: NS-398 is a non-steroidal anti-inflammatory agent with potent analgesic and antipyretic effects. It inhibits cyclooxygenase 2 (COX2) <Reference id=30409/><Reference id=30408/>.
iupac name: N-(2-cyclohexyloxy-4-nitrophenyl)methanesulfonamide
xref: CHEMBL7162
synonym: NS 398
approved: f
ligand name: NS-398
type: SyntheticOrganicLigand

PL265
in ch i key: HLACXNCYLIKGES-YCRNBWNJSA-N
in ch i: InChI=1S/C27H35N2O9P/c1-17(2)26(33)37-16-38-27(34)29-19(4)39(35,36)15-23(24(30)28-18(3)25(31)32)14-20-10-12-22(13-11-20)21-8-6-5-7-9-21/h5-13,17-19,23H,14-16H2,1-4H3,(H,28,30)(H,29,34)(H,31,32)(H,35,36)/t18-,19+,23+/m0/s1
comment: PL265 is a preclinical, long-acting dual ENKephalinase inhibitor (DENKi), with analgesic potential <Reference id=30794/>. See also <Ligand id=7896/>. PL265 has been developed as a novel therapeutic for control of intractable cancer pain. It is 'Example 4' claimed in patent US2014161839 <Reference id=30795/>.
iupac name: (2S)-2-[[(2S)-2-[[hydroxy-[(1R)-1-(2-methylpropanoyloxymethoxycarbonylamino)ethyl]phosphoryl]methyl]-3-(4-phenylphenyl)propanoyl]amino]propanoic acid
synonym: compound 2a [PMID: 25692029]
approved: f
ligand name: PL265
type: SyntheticOrganicLigand

etomoxir
canonical SMILES: CCOC(=O)C1(CCCCCCOc2ccc(cc2)Cl)OC1
isomeric SMILES: CCOC(=O)[C@]1(CCCCCCOc2ccc(cc2)Cl)OC1
in ch i key: DZLOHEOHWICNIL-QGZVFWFLSA-N
in ch i: InChI=1S/C17H23ClO4/c1-2-20-16(19)17(13-22-17)11-5-3-4-6-12-21-15-9-7-14(18)8-10-15/h7-10H,2-6,11-13H2,1H3/t17-/m1/s1
comment: Etomoxir is an irreversible inhibitor of mitochondrial carnitine palmitoyltransferase 1 (CPT1). It is one of the most widely used chemical probes for studying mitochondrial fatty acid β-oxidation. We show the (R) enantiomer, which is the active form responsible for fatty acid oxidation.
iupac name: ethyl (2R)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate
xref: CHEMBL1531556
synonym: rac-etomoxir ethyl ester
approved: f
ligand name: etomoxir
type: SyntheticOrganicLigand

clobetasone
in ch i key: XXIFVOHLGBURIG-OZCCCYNHSA-N
in ch i: InChI=1S/C22H26ClFO4/c1-12-8-16-15-5-4-13-9-14(25)6-7-19(13,2)21(15,24)17(26)10-20(16,3)22(12,28)18(27)11-23/h6-7,9,12,15-16,28H,4-5,8,10-11H2,1-3H3/t12-,15-,16-,19-,20-,21-,22-/m0/s1
comment: Clobetasone is a corticosteroid used in dermatology.
iupac name: (8S,9R,10S,13S,14S,16S,17R)-17-(2-chloroacetyl)-9-fluoro-17-hydroxy-10,13,16-trimethyl-7,8,12,14,15,16-hexahydro-6H-cyclopenta[a]phenanthrene-3,11-dione
synonym: Eumovate®
approved: t
ligand name: clobetasone
type: SyntheticOrganicLigand

pholcodine
in ch i key: GPFAJKDEDBRFOS-FKQDBXSBSA-N
in ch i: InChI=1S/C23H30N2O4/c1-24-7-6-23-16-3-4-18(26)22(23)29-21-19(5-2-15(20(21)23)14-17(16)24)28-13-10-25-8-11-27-12-9-25/h2-5,16-18,22,26H,6-14H2,1H3/t16-,17+,18-,22-,23-/m0/s1
comment: Pholcodine is an opioid cough suppressant (antitussive). It helps suppress unproductive coughs, has a mild sedative effect, but very limited analgesic effects.
iupac name: (4R,4aR,7S,7aR,12bS)-3-methyl-9-(2-morpholin-4-ylethoxy)-2,4,4a,7,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinoline-7-o
xref: CHEMBL2105224
synonym: Pavacol-D®
synonym: Galenphol®
synonym: Covonia Dry Cough®
approved: t
ligand name: pholcodine
type: SyntheticOrganicLigand

compound 42 [PMID: 26938474]
canonical SMILES: O=C1N(CCc2c1cccc2)c1ccc(cc1)c1cc[nH]n1
isomeric SMILES: O=C1N(CCc2c1cccc2)c1ccc(cc1)c1cc[nH]n1
in ch i key: NEEFLDGZGNPYSN-UHFFFAOYSA-N
in ch i: InChI=1S/C18H15N3O/c22-18-16-4-2-1-3-13(16)10-12-21(18)15-7-5-14(6-8-15)17-9-11-19-20-17/h1-9,11H,10,12H2,(H,19,20)
comment: Compound 42 is an inhibitor of branched chain aminotransferase 2 (BCAT2, a.k.a. BCATm) <Reference id=30750/>. GSK identified this molecule in a fragment screening and SAR study to identify BCAT2 inhibitors, which they suggest may have anti-obesity potential.
iupac name: 2-[4-(1H-pyrazol-3-yl)phenyl]-1,2,3,4-tetrahydroisoquinolin-1-one
approved: f
ligand name: compound 42 [PMID: 26938474]
type: SyntheticOrganicLigand

diamorphine
in ch i key: GVGLGOZIDCSQPN-PVHGPHFFSA-N
in ch i: InChI=1S/C21H23NO5/c1-11(23)25-16-6-4-13-10-15-14-5-7-17(26-12(2)24)20-21(14,8-9-22(15)3)18(13)19(16)27-20/h4-7,14-15,17,20H,8-10H2,1-3H3/t14-,15+,17-,20-,21-/m0/s1
comment: Diamorphine (heroin) is a morphine derivative. It acts as a potent opioid receptor agonist after deacetylation to 6-acetylmorphine and subsequently to morphine <Reference id=31930/>. Internationally, heroin is a controlled narcotic drug.
iupac name: [(4R,4aR,7S,7aR,12bS)-9-acetyloxy-3-methyl-2,4,4a,7,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinoline-7-yl] acetate
xref: CHEMBL459324
synonym: heroin
synonym: diacetylmorphine
synonym: acetomorphine
approved: f
ligand name: diamorphine
type: SyntheticOrganicLigand

dipipanone
in ch i key: SVDHSZFEQYXRDC-UHFFFAOYSA-N
in ch i: InChI=1S/C24H31NO/c1-3-23(26)24(21-13-7-4-8-14-21,22-15-9-5-10-16-22)19-20(2)25-17-11-6-12-18-25/h4-5,7-10,13-16,20H,3,6,11-12,17-19H2,1-2H3
comment: Dipipanone is a strong opioid analgesic drug. The INN record specifies a mixture of enantiomers. We show the non-stereo molecule to represent the mixture.
iupac name: 4,4-di(phenyl)-6-piperidin-1-ylheptan-3-one
xref: CHEMBL2111157
synonym: Diconal tablets (dipipanone+cyclizine)
synonym: pipadone
approved: t
ligand name: dipipanone
type: SyntheticOrganicLigand

MRL-248
in ch i key: ODEANEWMWSRFHI-UHFFFAOYSA-N
comment: MRL-248 is a selective, small molecule antagonist of RORγt, an isoform of RORγ (RAR related orphan receptor C), with antiinflammatory potential <Reference id=30736/>.
iupac name: 4-{1-[2-chloro-6-(trifluoromethyl)benzoyl]-1H,3aH,7aH-pyrazolo[4,3-b]pyridin-3-yl}-3-fluorobenzoic acid
approved: f
ligand name: MRL-248
type: SyntheticOrganicLigand

MRL-367
in ch i key: LCOVNUGQIUYGLV-UHFFFAOYSA-N
comment: MRL-367 is a selective, small molecule antagonist of RORγt, an isoform of RORγ (RAR related orphan receptor C), with antiinflammatory potential <Reference id=30736/>.
iupac name: 4-{1-[2-chloro-6-(trifluoromethyl)benzoyl]-1H,3aH,7aH-pyrazolo[4,3-b]pyridin-3-yl}-5-fluoro-2-hydroxybenzoic acid
approved: f
ligand name: MRL-367
type: SyntheticOrganicLigand

compound 15 [PMID: 25411721]
in ch i key: FMASTMURQSHELY-UHFFFAOYSA-N
in ch i: InChI=1S/C24H22FN3O/c1-15-11-19(25)7-8-23(15)28(24(29)20-9-10-26-13-16(20)2)14-18-5-4-6-22-21(18)12-17(3)27-22/h4-13,27H,14H2,1-3H3
comment: Compound 15 is an agonist of the bile acid receptor 1 (GPBAR1), which has been used experimentally to show that GPBAR1 plays a regulatory role in inflammation <Reference id=30730/>. This is example 252 claimed in patent WO2007110237 <Reference id=30731/>.
iupac name: N-(4-fluoro-2-methylphenyl)-3-methyl-N-[(2-methyl-1H-indol-4-yl)methyl]pyridine-4-carboxamide
synonym: example 252 [WO2007110237]
approved: f
ligand name: compound 15 [PMID: 25411721]
type: SyntheticOrganicLigand

example 13 [WO2009109743]
in ch i key: VSQUREFTKYDATG-UHFFFAOYSA-N
in ch i: InChI=1S/C19H17N5O2/c25-19(22-17-7-4-10-21-23-17)24-12-16(13-24)26-18-9-8-15(11-20-18)14-5-2-1-3-6-14/h1-11,16H,12-13H2,(H,22,23,25)
comment: This is one of the fatty acid amide hydrolase 1 (FAAH) inhibitor compounds claimed in patent WO2009109743 <Reference id=30725/>. FAAH inhibitors are being investigated for their potential analgesic action.
iupac name: 3-(5-phenylpyridin-2-yl)oxy-N-pyridazin-3-ylazetidine-1-carboxamide
approved: f
ligand name: example 13 [WO2009109743]
type: SyntheticOrganicLigand

estramustine
in ch i key: FRPJXPJMRWBBIH-RBRWEJTLSA-N
in ch i: InChI=1S/C23H31Cl2NO3/c1-23-9-8-18-17-5-3-16(29-22(28)26(12-10-24)13-11-25)14-15(17)2-4-19(18)20(23)6-7-21(23)27/h3,5,14,18-21,27H,2,4,6-13H2,1H3/t18-,19-,20+,21+,23+/m1/s1
comment: Estramustine is a synthetic analogue combining estradiol and nornitrogen mustard. It is a DNA alkylating agent with antineoplastic activity. Marketed formulations contain estramustine phosphate sodium (PubChem CID 444000).
iupac name: [(8R,9S,13S,14S,17S)-17-hydroxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-yl] N,N-bis(2-chloroethyl)carbamate
xref: CHEMBL1575
synonym: Estracyt®
synonym: Emcyt®
approved: t
ligand name: estramustine
type: SyntheticOrganicLigand

dacarbazine
canonical SMILES: CN(N=Nc1[nH]cnc1C(=O)N)C
isomeric SMILES: CN(N=Nc1[nH]cnc1C(=O)N)C
in ch i key: FDKXTQMXEQVLRF-UHFFFAOYSA-N
in ch i: InChI=1S/C6H10N6O/c1-12(2)11-10-6-4(5(7)13)8-3-9-6/h3H,1-2H3,(H2,7,13)(H,8,9)
comment: Dacarbazine is a triazine DNA alkylating agent.
xref: CHEMBL1574179
synonym: DTIC-Dome®
approved: t
ligand name: dacarbazine
type: SyntheticOrganicLigand

echothiophate
canonical SMILES: CCOP(=O)(SCC[N+](C)(C)C)OCC
isomeric SMILES: CCOP(=O)(SCC[N+](C)(C)C)OCC
in ch i key: BJOLKYGKSZKIGU-UHFFFAOYSA-N
in ch i: InChI=1S/C9H23NO3PS/c1-6-12-14(11,13-7-2)15-9-8-10(3,4)5/h6-9H2,1-5H3/q+1
comment: Echothiophate is the parent molecule of the irreversible cholinesterase inhibitor echothiophate iodide (PubChem CID 10547).
xref: CHEMBL1201341
synonym: ecostigmine iodide
synonym: phospholine iodide
approved: t
ligand name: echothiophate
type: SyntheticOrganicLigand

edrophonium
canonical SMILES: CC[N+](c1cccc(c1)O)(C)C
isomeric SMILES: CC[N+](c1cccc(c1)O)(C)C
in ch i key: VWLHWLSRQJQWRG-UHFFFAOYSA-O
in ch i: InChI=1S/C10H15NO/c1-4-11(2,3)9-6-5-7-10(12)8-9/h5-8H,4H2,1-3H3/p+1
comment: Edrophonium is the parent molecule of the clinically used rapid-onset, short-acting cholinesterase inhibitor edrophonium chloride (PubChem CID 8307).
iupac name: ethyl-(3-hydroxyphenyl)-dimethylazanium
xref: CHEMBL1104
synonym: Tensilon®
synonym: Enlon®
approved: t
ligand name: edrophonium
type: SyntheticOrganicLigand

cinnarizine
isomeric SMILES: c1ccc(cc1)/C=C/CN1CCN(CC1)C(c1ccccc1)c1ccccc1
in ch i key: DERZBLKQOCDDDZ-JLHYYAGUSA-N
in ch i: InChI=1S/C26H28N2/c1-4-11-23(12-5-1)13-10-18-27-19-21-28(22-20-27)26(24-14-6-2-7-15-24)25-16-8-3-9-17-25/h1-17,26H,18-22H2/b13-10+
comment: Cinnarizine is used primarily for its anti-histaminic activity, but it also has anti-cholinergic and calcium channel blocking effects, which may account for some of its side-effects.The INN record for this drug specifies cinnarizine clofibrate (PubChem CID 6436096).
iupac name: 1-[di(phenyl)methyl]-4-(3-phenylprop-2-enyl)piperazine
xref: CHEMBL43064
synonym: R-1575
synonym: R 1575
synonym: Stugeron®
approved: t
ligand name: cinnarizine
type: SyntheticOrganicLigand

plecanatide
in ch i key: NSPHQWLKCGGCQR-DLJDZFDSSA-N
comment: Plecanatide is a synthetic analogue of <Ligand id=5084/>, which is an agonist of the guanylate cyclase C (GC-C) receptor (GUCY2C) <Reference id=30716/>. Activation of GC-C in mucosal epithelial cells of the gastrointestinal (GI) tract causes the secretion of fluid, facilitating bowel movements. Plecanatide has potential to help manage constipating GI disorders, such as chronic idiopathic constipation and constipation-predominant irritable bowel syndrome (IBS-C). Plecanatide is one of the peptides claimed in patent WO2014151206, where it is represented by SEQ ID NO: 1 and code SP-304, with residue 3 (Aad) being gultamic acid (E, Glu) <Reference id=30718/>. The SMILES and structure image used in this entry are from Chemicalize. HELM notation is PEPTIDE1{N.D.E.C.E.L.C.V.N.V.A.C.T.G.C.L}$PEPTIDE1,PEPTIDE1,12:R3-4:R3|PEPTIDE1,PEPTIDE1,15:R3-7:R3$$$. <Ligand id=5017/> was the first GC-C activator to reach the clinic, like plecanatide it is approved for the treatment of chronic constipation and IBS-C.
xref: CHEMBL2103867
synonym: SP-304
synonym: [3-glutamic acid(D>E)]human uroguanylin
synonym: Trulance®
approved: t
ligand name: plecanatide
type: PeptideLigand

vosoritide
in ch i key: IGYWDDBBJPSOTG-WBAGYEQSSA-N
comment: Vosoritide is a cyclic analogue of C-type natriuretic peptide (CNP) that has a longer half-life (duration of action) than the endogenous peptide <Reference id=30714/>. It comprises the 37 C-terminal amino acids from human CNP with the addition of proline and glycine (PG) at its N-terminal. Vosoritide represents a novel mechanism which has the potential to treat mutant fibroblast growth factor receptor 3-driven achondroplasia, by stimulating endochondral ossification and thereby ameliorating impaired bone growth <Reference id=30715/><Reference id=30714/><Reference id=42702/>.
synonym: BMN-111
synonym: BMN 111
synonym: Voxzogo®
approved: t
ligand name: vosoritide
type: PeptideLigand

telaglenastat
in ch i key: PRAAPINBUWJLGA-UHFFFAOYSA-N
comment: Telaglenastat (CB-839) is an investigational noncompetitive (allosteric) glutaminase inhibitor <Reference id=30675/>. It is one of the structures claimed in patent US8604016 <Reference id=30678/>, where it is compound 670. The anti-cancer activity of CB-839 was first reported in preclinical studies in triple-negative breast cancer (TNBC) cells in vitro and in vivo <Reference id=30675/>.
iupac name: N-[6-[4-[5-[(2-pyridin-2-ylacetyl)amino]-1,3,4-thiadiazol-2-yl]butyl]pyridazin-3-yl]-2-[3-(trifluoromethoxy)phenyl]acetamide
synonym: CB839
synonym: CB 839
synonym: CB-839
approved: f
ligand name: telaglenastat
type: SyntheticOrganicLigand

(-)-HIP-A
canonical SMILES: OC(=O)C1NCC2C1C(=NO2)O
isomeric SMILES: OC(=O)[C@H]1NC[C@H]2[C@@H]1C(=NO2)O
in ch i key: XJSXFNHFIBCTDU-HZLVTQRSSA-N
in ch i: InChI=1S/C6H8N2O4/c9-5-3-2(12-8-5)1-7-4(3)6(10)11/h2-4,7H,1H2,(H,8,9)(H,10,11)/t2-,3-,4-/m0/s1
iupac name: (3aR,4S,6aR)-3-hydroxy-3aH,4H,5H,6H,6aH-pyrrolo[3,4-d][1,2]oxazole-4-carboxylic acid
xref: CHEMBL334583
approved: f
ligand name: (-)-HIP-A
type: SyntheticOrganicLigand

cenderitide
in ch i key: YZEJNKFJIYNYMP-MGAVOHMASA-N
comment: Cenderitide is a designed chimeric natriuretic peptide (NP) engineered to co-activate the two known NP receptors, guanylyl cyclase (GC) -A and -B <Reference id=30711/>. It comprises the sequence for <Ligand id=4896/> at the N-terminus (residues 1-22) joined to 15 amino acids (23-37) of the C-terminus of Dendroaspis natriuretic peptide (DNP), isolated from the venom of the green Mamba snake Dendroaspis angusticeps. Synthetic DNP has useful renal activity <Reference id=30709/>. Cenderitide combines the beneficial vascular and antiproliferative properties of CNP with the potent natriuretic and diuretic hypotensive effects of DNP.
xref: CHEMBL2108721
synonym: CD-NP
approved: f
ligand name: cenderitide
type: PeptideLigand

celiprolol
in ch i key: JOATXPAWOHTVSZ-UHFFFAOYSA-N
in ch i: InChI=1S/C20H33N3O4/c1-7-23(8-2)19(26)22-15-9-10-18(17(11-15)14(3)24)27-13-16(25)12-21-20(4,5)6/h9-11,16,21,25H,7-8,12-13H2,1-6H3,(H,22,26)
comment: Celiprolol is a cardioselective β1-adrenoceptor antagonist, but also displays weak partial agonist (sympathomimetic) action at β2-adrenoceptors.
iupac name: 3-[3-acetyl-4-[3-(tert-butylamino)-2-hydroxypropoxy]phenyl]-1,1-diethylurea
xref: CHEMBL27810
synonym: Celectol®
synonym: Selectol®
synonym: REV 5320
synonym: ST-1396
synonym: ST1396
approved: t
ligand name: celiprolol
type: SyntheticOrganicLigand

enoximone
canonical SMILES: CSc1ccc(cc1)C(=O)c1[nH]c(=O)[nH]c1C
isomeric SMILES: CSc1ccc(cc1)C(=O)c1[nH]c(=O)[nH]c1C
in ch i key: ZJKNESGOIKRXQY-UHFFFAOYSA-N
in ch i: InChI=1S/C12H12N2O2S/c1-7-10(14-12(16)13-7)11(15)8-3-5-9(17-2)6-4-8/h3-6H,1-2H3,(H2,13,14,16)
comment: Enoximone is a selective phosphodiesterase inhibitor, targeting PDE3 subtypes <Reference id=30705/>. It is a cardiotonic agent <Reference id=30703/><Reference id=30704/>.
iupac name: 4-methyl-5-(4-methylsulfanylbenzoyl)-1,3-dihydroimidazol-2-one
xref: CHEMBL249856
synonym: fenoximone
synonym: MDL 17,043
synonym: MDL-17,043
synonym: Perfan®
synonym: MDL-17043
approved: t
ligand name: enoximone
type: SyntheticOrganicLigand

PF-04905428
in ch i key: FUCKCIVGBCBZNP-MRXNPFEDSA-N
in ch i: InChI=1S/C22H29ClN4O6/c1-33-13-16(28)12-26-19(29)11-25-27(21(26)31)15-6-7-18(23)17(10-15)20(30)24-14-22(32)8-4-2-3-5-9-22/h6-7,10-11,16,28,32H,2-5,8-9,12-14H2,1H3,(H,24,30)/t16-/m1/s1
comment: PF-04905428 is an investigational purinergic receptor 2 (P2X7) antagonist <Reference id=30699/><Reference id=30700/>, with potential antiinflammatory action in various conditions such as arthritis, allergies, asthma, COPD, autoimmune diseases and other disorders.. PF-04905428 is one of the compounds claimed in patent US6974812 <Reference id=30701/>.
iupac name: 2-chloro-N-[(1-hydroxycycloheptyl)methyl]-5-[4-[(2R)-2-hydroxy-3-methoxypropyl]-3,5-dioxo-1,2,4-triazin-2-yl]benzamide
xref: CHEMBL1823817
synonym: CE-224535
synonym: CE-224,535
synonym: compound 33 [PMID: 21565499]
synonym: compound 3 [PMID: 21782426]
approved: f
ligand name: PF-04905428
type: SyntheticOrganicLigand

PF-03882845
in ch i key: XNULRSOGWPFPBL-REWPJTCUSA-N
in ch i: InChI=1S/C24H22ClN3O2/c25-21-12-18(8-5-17(21)13-26)28-23(14-3-1-2-4-14)20-10-6-15-11-16(24(29)30)7-9-19(15)22(20)27-28/h5,7-9,11-12,14,20,23H,1-4,6,10H2,(H,29,30)/t20-,23-/m0/s1
comment: PF-03882845 is an investigational, potent and selective, non-steroidal mineralocorticoid receptor antagonist <Reference id=30697/>, with potential protective effect in aldosterone-mediated renal damage (nephropathy).
iupac name: (3S,3aR)-2-(3-chloro-4-cyanophenyl)-3-cyclopentyl-3,3a,4,5-tetrahydrobenzo[g]indazole-7-carboxylic acid
xref: CHEMBL1215331
synonym: compound 2 [PMID: 24738581]
synonym: PF-3882845
approved: f
ligand name: PF-03882845
type: SyntheticOrganicLigand

PF-05190457
in ch i key: ZIUDADZJCKGWKR-AREMUKBSSA-N
in ch i: InChI=1S/C29H32N6OS/c1-19-11-25(31-18-30-19)22-3-5-24-21(12-22)4-6-26(24)35-16-29(17-35)7-9-33(10-8-29)27(36)13-23-15-34-14-20(2)37-28(34)32-23/h3,5,11-12,14-15,18,26H,4,6-10,13,16-17H2,1-2H3/t26-/m1/s1
comment: PF-05190457 is a selective, orally bioavailable and competitive antagonist of the ghrelin receptor <Reference id=30696/>, with potential therapeutic utility for the treatment of obesity and type 2 diabetes <Reference id=30695/>.
iupac name: 2-(2-methylimidazo[2,1-b][1,3]thiazol-6-yl)-1-[2-[(1R)-5-(6-methylpyrimidin-4-yl)-2,3-dihydro-1H-inden-1-yl]-2,7-diazaspiro[3.5]nonan-7-yl]ethanone
xref: CHEMBL3287218
synonym: PF-5190457
approved: f
ligand name: PF-05190457
type: SyntheticOrganicLigand

PF-04995274
in ch i key: WLLOFQROROXOMO-GOSISDBHSA-N
in ch i: InChI=1S/C23H32N2O6/c26-23(7-12-27-13-8-23)16-25-9-4-17(5-10-25)14-29-22-21-19(30-18-6-11-28-15-18)2-1-3-20(21)31-24-22/h1-3,17-18,26H,4-16H2/t18-/m1/s1
comment: PF-04995274 is a serotonin 5-HT4 receptor partial agonist, developed as a potential pro-cognitive agent for the treatment of Alzheimer's disease (AD) <Reference id=30694/>.
iupac name: 4-[[4-[[4-[(3R)-oxolan-3-yl]oxy-1,2-benzoxazol-3-yl]oxymethyl]piperidin-1-yl]methyl]oxan-4-ol
xref: CHEMBL2152922
synonym: compound 2d [PMID: 22974325]
synonym: PF04995274
synonym: PF 04995274
approved: f
ligand name: PF-04995274
type: SyntheticOrganicLigand

PF-03654746
in ch i key: SXMBKHYDZOCBMT-UHFFFAOYSA-N
in ch i: InChI=1S/C18H24F2N2O/c1-2-21-17(23)14-10-18(20,11-14)15-6-5-13(16(19)9-15)12-22-7-3-4-8-22/h5-6,9,14H,2-4,7-8,10-12H2,1H3,(H,21,23)
comment: PF-03654746 is a potent and selective, investigational histamine H3 receptor antagonist <Reference id=30692/>, with potetial as an antiinflammatory agent <Reference id=30691/> and with potential to treat human cognitive disorders.
iupac name: N-ethyl-3-fluoro-3-[3-fluoro-4-(pyrrolidin-1-ylmethyl)phenyl]cyclobutane-1-carboxamide
xref: CHEMBL2151197
synonym: PF03654746
synonym: PF 03654746
synonym: compound 6 [PMID: 21928839]
approved: f
ligand name: PF-03654746
type: SyntheticOrganicLigand

loreclezole
canonical SMILES: Clc1ccc(c(c1)Cl)C(=Cn1cncn1)Cl
isomeric SMILES: Clc1ccc(c(c1)Cl)/C(=C/n1cncn1)/Cl
in ch i key: XGLHZTBDUXXHOM-WMZJFQQLSA-N
in ch i: InChI=1S/C10H6Cl3N3/c11-7-1-2-8(9(12)3-7)10(13)4-16-6-14-5-15-16/h1-6H/b10-4-
iupac name: 1-[(Z)-2-chloro-2-(2,4-dichlorophenyl)ethenyl]-1H-1,2,4-triazole
xref: CHEMBL1397886
synonym: R 72063
approved: f
ligand name: loreclezole
type: SyntheticOrganicLigand

PF-03463275
in ch i key: KYLOBHXXQOZRKK-YIONKMFJSA-N
in ch i: InChI=1S/C19H22ClFN4O/c1-23-7-13-14(8-23)15(13)9-25(19(26)18-10-24(2)11-22-18)6-12-3-4-17(21)16(20)5-12/h3-5,10-11,13-15H,6-9H2,1-2H3/t13-,14+,15?
comment: PF-03463275 is an orally available, CNS-penetrant inhibitor of SLC6A9, the GlyT1 glycine transporter <Reference id=30690/>, developed for potential anti-schizophrenia activity. This entry represents the parent molecule. Its hydrochloride salt has PubChem CID 91799199.
iupac name: N-[(3-chloro-4-fluorophenyl)methyl]-1-methyl-N-[[(1R,5S)-3-methyl-3-azabicyclo[3.1.0]hexan-6-yl]methyl]imidazole-4-carboxamide
xref: CHEMBL563251
synonym: PF-3463275
synonym: KB-79869
synonym: compound 10 [PMID: 19410451]
approved: f
ligand name: PF-03463275
type: SyntheticOrganicLigand

CP-601927
canonical SMILES: FC(c1ccc2c(c1)C1CNCC2C1)(F)F
isomeric SMILES: FC(c1ccc2c(c1)[C@H]1CNC[C@@H]2C1)(F)F
in ch i key: RNOBTWYQAWEZHH-JGVFFNPUSA-N
in ch i: InChI=1S/C12H12F3N/c13-12(14,15)9-1-2-10-7-3-8(6-16-5-7)11(10)4-9/h1-2,4,7-8,16H,3,5-6H2/t7-,8+/m0/s1
comment: CP-601927 is an orally available, CNS‐penetrant, high affinity, selective, investigational partial agonist of the nicotinic acetylcholine (nAch) receptor α4β2 <Reference id=30687/>, developed for its potential in several central nervous system conditions <Reference id=30689/>. CP-601927 was investigated for its potential to augment antidepressant treatment in patients with major depressive disorder <Reference id=30688/>.
synonym: CP-601,927
synonym: CP 601927
approved: f
ligand name: CP-601927
type: SyntheticOrganicLigand

CE-326597
in ch i key: UBNMGTSDHSQBEL-PMERELPUSA-N
in ch i: InChI=1S/C37H34N6O2/c1-25(2)41(23-26-13-5-3-6-14-26)34(44)24-42-32-19-11-12-20-33(32)43-35(27-15-7-4-8-16-27)39-40-36(43)30(37(42)45)21-28-22-38-31-18-10-9-17-29(28)31/h3-20,22,25,30,38H,21,23-24H2,1-2H3/t30-/m0/s1
comment: CE-326597 is an an orally active, gut-selective cholecystokinin (CCK) type A receptor (CCKAR) agonist, developed for its anti-obesity potential <Reference id=30686/><Reference id=30685/>.
iupac name: N-benzyl-2-[(4S)-4-(1H-indol-3-ylmethyl)-5-oxo-1-phenyl-4H-[1,2,4]triazolo[3,4-d][1,5]benzodiazepin-6-yl]-N-propan-2-ylacetamide
xref: CHEMBL1269258
synonym: compound 4a [PMID: 20851601]
approved: f
ligand name: CE-326597
type: SyntheticOrganicLigand

PF-04191834
in ch i key: DVNQWYLVSNPCJZ-UHFFFAOYSA-N
in ch i: InChI=1S/C22H23N3O2S/c1-25-20(9-12-24-25)16-5-7-18(8-6-16)28-19-4-2-3-17(15-19)22(21(23)26)10-13-27-14-11-22/h2-9,12,15H,10-11,13-14H2,1H3,(H2,23,26)
comment: PF-4191834 is an orally available, novel, selective non-redox 5-lipoxygenase (ALOX5) inhibitor with potential antiinflammatory and analgesic activity <Reference id=30681/>.
iupac name: 4-[3-[4-(2-methylpyrazol-3-yl)phenyl]sulfanylphenyl]oxane-4-carboxamide
synonym: PF 4191834
synonym: PF4191834
synonym: PF-4191834
approved: f
ligand name: PF-04191834
type: SyntheticOrganicLigand

tilfrinib
canonical SMILES: Oc1cccc(c1)NC1=CC=NC2C1C1C=CC=CC1N2
isomeric SMILES: Oc1cccc(c1)NC1=CC=NC2C1C1C=CC=CC1N2
in ch i key: YLLRPQWLASQXSI-UHFFFAOYSA-N
in ch i: InChI=1S/C17H17N3O/c21-12-5-3-4-11(10-12)19-15-8-9-18-17-16(15)13-6-1-2-7-14(13)20-17/h1-10,13-14,16-17,19-21H
comment: Tilfrinib is a selective inhibitor of protein tyrosine kinase 6 (a.k.a. Brk) <Reference id=30674/>. Although tilfrinib, sounds like a non-proprietary name (INN), it is not registered with the WHO MedNet INN service.
iupac name: 3-({4aH,4bH,8aH,9H,9aH-pyrido[2,3-b]indol-4-yl}amino)phenol
synonym: compound 4f [PMID: 24650640]
approved: f
ligand name: tilfrinib
type: SyntheticOrganicLigand

JNJ40355003
in ch i key: CTYVKSQPMCSUOR-UHFFFAOYSA-N
in ch i: InChI=1S/C23H23ClN4O2/c24-19-6-8-21(9-7-19)30-22-5-1-3-18(15-22)17-27-11-13-28(14-12-27)23(29)26-20-4-2-10-25-16-20/h1-10,15-16H,11-14,17H2,(H,26,29)
comment: JNJ40355003 is a potent, selective and irreversible inhibitor of fatty acid amide hydrolase (FAAH) <Reference id=30673/>.
iupac name: 4-[[3-(4-chlorophenoxy)phenyl]methyl]-N-pyridin-3-ylpiperazine-1-carboxamide
xref: CHEMBL2164602
synonym: JNJ-40355003
synonym: compound 23 [PMID: 24900385]
approved: f
ligand name: JNJ40355003
type: SyntheticOrganicLigand

bimosiamose
in ch i key: RYWCQJDEHXJHRI-XJMXIVSISA-N
in ch i: InChI=1S/C46H54O16/c47-23-35-39(53)41(55)43(57)45(61-35)59-33-15-13-25(19-31(33)29-11-5-9-27(17-29)21-37(49)50)7-3-1-2-4-8-26-14-16-34(60-46-44(58)42(56)40(54)36(24-48)62-46)32(20-26)30-12-6-10-28(18-30)22-38(51)52/h5-6,9-20,35-36,39-48,53-58H,1-4,7-8,21-24H2,(H,49,50)(H,51,52)/t35-,36-,39-,40-,41+,42+,43+,44+,45+,46+/m1/s1
comment: Bimosiamose is a synthetic pan-selectin antagonist <Reference id=30671/> being investigated as a novel anti-inflammatory agent, primarily for controlling allergic respiratory diseases <Reference id=30662/><Reference id=30664/>, but it has also been reported to provide benefit in ischemia/reperfusion injury <Reference id=30663/><Reference id=30665/><Reference id=30666/><Reference id=30667/><Reference id=30668/>. The primary role of selectin inhibitors appears to be disruption of early events in the migration process (possibly mediated through E-selectin <Reference id=30669/>), thereby inhibiting their eventual extravasation from blood to the inflammed tissue.
iupac name: 2-[3-[5-[6-[3-[3-(carboxymethyl)phenyl]-4-[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]hexyl]-2-[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]phenyl]acetic acid
xref: CHEMBL1215923
synonym: TBC 1269
synonym: TBC-1269
synonym: TBC1269
synonym: compound 15e [PMID: 9544210]
approved: f
ligand name: bimosiamose
type: SyntheticOrganicLigand

MK-0812
in ch i key: MTMDXAIUENDNDL-RJSMDTJLSA-N
in ch i: InChI=1S/C24H34F3N3O3/c1-15(2)23(7-4-18(11-23)29-20-6-9-33-14-21(20)32-3)22(31)30-8-5-19-16(13-30)10-17(12-28-19)24(25,26)27/h10,12,15,18,20-21,29H,4-9,11,13-14H2,1-3H3/t18-,20+,21-,23+/m1/s1
comment: MK-0812 is an antagonist of chemokine (C-C motif) receptor 2 (the CCR2 chemokine receptor) <Reference id=30661/> being investigated for its anti-inflammatory action.
iupac name: [(1S,3R)-3-[[(3S,4S)-3-methoxyoxan-4-yl]amino]-1-propan-2-ylcyclopentyl]-[3-(trifluoromethyl)-7,8-dihydro-5H-1,6-naphthyridin-6-yl]methanone
xref: CHEMBL3305901
synonym: MK0812
approved: f
ligand name: MK-0812
type: SyntheticOrganicLigand

vercirnon
canonical SMILES: Clc1ccc(c(c1)C(=O)c1cc[n+](cc1)[O-])NS(=O)(=O)c1ccc(cc1)C(C)(C)C
isomeric SMILES: Clc1ccc(c(c1)C(=O)c1cc[n+](cc1)[O-])NS(=O)(=O)c1ccc(cc1)C(C)(C)C
in ch i key: JRWROCIMSDXGOZ-UHFFFAOYSA-N
comment: Vercirnon (CCX282-B) is a selective, potent and orally bioavailable antagonist of the chemokine (C-C motif) receptor 9 (CCR9 chemokine receptor) <Reference id=30657/>. It was developed for potential to treat inflammatory bowel disease.
iupac name: 4-tert-butyl-N-[4-chloro-2-(1-oxidopyridin-1-ium-4-carbonyl)phenyl]benzenesulfonamide
xref: CHEMBL2178578
synonym: Traficet-EN
synonym: GSK1605786
synonym: GSK'786
synonym: CCX282-B
synonym: GSK1605786A
approved: f
ligand name: vercirnon
type: SyntheticOrganicLigand

INCB3284
in ch i key: NXZNYBUBXWWKCP-JMOWIOHXSA-N
in ch i: InChI=1S/C26H31F3N4O4/c1-37-23-6-5-19(14-30-23)25(36)10-7-21(8-11-25)33-12-9-20(16-33)32-22(34)15-31-24(35)17-3-2-4-18(13-17)26(27,28)29/h2-6,13-14,20-21,36H,7-12,15-16H2,1H3,(H,31,35)(H,32,34)/t20-,21?,25?/m1/s1
comment: INCB3284 is a potent, selective and orally available small molecule antagonist of the chemokine (C-C motif) receptor 2 (CCR2; the primary receptor for <Ligand id=771/> (MCP-1)) <Reference id=30656/>, which was developed for potential anti-inflammatory activity and the treatment of inflammation-driven diseases. Note that alternative isomeric forms of this compound are presented by different online resources (e.g. CHEMBL1963131 and CHEMBL1951790).
iupac name: N-[2-[[(3R)-1-[4-hydroxy-4-(6-methoxypyridin-3-yl)cyclohexyl]pyrrolidin-3-yl]amino]-2-oxoethyl]-3-(trifluoromethyl)benzamide
synonym: INCB 3284
synonym: compound 13 [PMID: 24900329]
approved: f
ligand name: INCB3284
type: SyntheticOrganicLigand

difelikefalin
in ch i key: FWMNVWWHGCHHJJ-SKKKGAJSSA-N
in ch i: InChI=1S/C36H53N7O6/c1-24(2)21-29(32(45)40-28(15-9-10-18-37)34(47)43-19-16-36(39,17-20-43)35(48)49)42-33(46)30(23-26-13-7-4-8-14-26)41-31(44)27(38)22-25-11-5-3-6-12-25/h3-8,11-14,24,27-30H,9-10,15-23,37-39H2,1-2H3,(H,40,45)(H,41,44)(H,42,46)(H,48,49)/t27-,28-,29-,30-/m1/s1
comment: Difelikefalin is a first-in-class, peripherally acting, highly selective peptide agonist of the κ-opioid receptor, that was developed potential to treat chronic itch <Reference id=30645/> and it is claimed in patent US7402564B1 <Reference id=30644/>. This patent provides extensive results from preclinical testing, assessing the analgesic and anti-pruritic potential of difelikefalin.
iupac name: 4-amino-1-[(2R)-6-amino-2-[[(2R)-2-[[(2R)-2-[[(2R)-2-amino-3-phenylpropanoyl]amino]-3-phenylpropanoyl]amino]-4-methylpentanoyl]amino]hexanoyl]piperidine-4-carboxylic acid
synonym: SEQ ID NO: 2
synonym: D-Phe-D-Phe-D-Leu-D-Lys-[γ-(4-N-piperidinyl)amino carboxylic acid]
synonym: CR845
synonym: FE-202845
synonym: Korsuva®
synonym: Kapruvia®
approved: t
ligand name: difelikefalin
type: PeptideLigand

apalutamide
in ch i key: HJBWBFZLDZWPHF-UHFFFAOYSA-N
comment: Apalutamide is a novel androgen receptor (AR) antagonist (antiandrogen) that is approved as a treatment for castration-resistant prostate cancer (CRPC) <Reference id=30642/>. This compound (91) was discovered in a structure/activity relationship-guided medicinal chemistry program designed to identify antiandrogens devoid of agonistic activity in the setting of androgen receptor overexpression <Reference id=30643/>.
iupac name: 4-[7-[6-cyano-5-(trifluoromethyl)pyridin-3-yl]-8-oxo-6-sulfanylidene-5,7-diazaspiro[3.4]octan-5-yl]-2-fluoro-N-methylbenzamide
xref: CHEMBL3183409
synonym: Erleada®
synonym: ARN-509
synonym: ARN509
synonym: JNJ-56021927
approved: t
ligand name: apalutamide
type: SyntheticOrganicLigand

evocalcet
in ch i key: RZNUIYPHQFXBAN-XLIONFOSSA-N
in ch i: InChI=1S/C24H26N2O2/c1-17(22-8-4-6-19-5-2-3-7-23(19)22)25-20-13-14-26(16-20)21-11-9-18(10-12-21)15-24(27)28/h2-12,17,20,25H,13-16H2,1H3,(H,27,28)/t17-,20+/m1/s1
comment: Evocalcet is an investigational calcium-sensing receptor (CASR) agonist, or calcimimetic. CASR is a G protein-coupled receptor. This compound is claimed in patent US8362274 <Reference id=30641/>.
iupac name: 2-[4-[(3S)-3-[[(1R)-1-naphthalen-1-ylethyl]amino]pyrrolidin-1-yl]phenyl]acetic acid
synonym: MT-4580
synonym: MT 4580
synonym: MT4580
synonym: KHK-7580
synonym: KHK7580
synonym: KHK 7580
approved: f
ligand name: evocalcet
type: SyntheticOrganicLigand

brivaracetam
canonical SMILES: CCCC1CN(C(=O)C1)C(C(=O)N)CC
isomeric SMILES: CCC[C@H]1CN(C(=O)C1)[C@H](C(=O)N)CC
in ch i key: MSYKRHVOOPPJKU-BDAKNGLRSA-N
in ch i: InChI=1S/C11H20N2O2/c1-3-5-8-6-10(14)13(7-8)9(4-2)11(12)15/h8-9H,3-7H2,1-2H3,(H2,12,15)/t8-,9+/m1/s1
comment: Brivaracetam is a 4-n-propyl analogue of <Ligand id=6826/> with anticonvulsant properties <Reference id=30636/>. Like levetiracetam this drug inhibits synaptic vesicle protein 2A (SV2A), but with 10X higher binding affinity. Brivaracetam is brain penetrant and has a fast onset of action <Reference id=30638/>. It can also inhibit sodium channels.
iupac name: (2S)-2-[(4R)-2-oxo-4-propylpyrrolidin-1-yl]butanamide
xref: CHEMBL607400
synonym: UCB-34714
synonym: UCB34714
synonym: 2-(2-oxo-4-propylpyrrolidin-1-yl)butanamide
synonym: UCB 34714
synonym: Briviact®
synonym: compound 83α
approved: t
ligand name: brivaracetam
type: SyntheticOrganicLigand

selonsertib
in ch i key: YIDDLAAKOYYGJG-UHFFFAOYSA-N
in ch i: InChI=1S/C24H24FN7O/c1-14(2)32-13-27-30-23(32)19-5-4-6-22(28-19)29-24(33)17-10-21(15(3)9-18(17)25)31-11-20(26-12-31)16-7-8-16/h4-6,9-14,16H,7-8H2,1-3H3,(H,28,29,33)
comment: Selonsertib is an orally bioavailable apoptosis signal-regulating kinase 1 (ASK1= mitogen-activated protein kinase kinase kinase 5, MAP3K5) inhibitor being investigated for its anti-fibrotic activity. It is compound I in patent US8742126 <Reference id=30633/>. Development as a treatment for nonalcoholic steatohepatitis (NASH) was unsuccessful.
iupac name: 5-(4-cyclopropylimidazol-1-yl)-2-fluoro-4-methyl-N-[6-(4-propan-2-yl-1,2,4-triazol-3-yl)pyridin-2-yl]benzamide
synonym: GS-4997
approved: f
ligand name: selonsertib
type: SyntheticOrganicLigand

erdafitinib
in ch i key: OLAHOMJCDNXHFI-UHFFFAOYSA-N
in ch i: InChI=1S/C25H30N6O2/c1-17(2)26-8-9-31(20-10-21(32-4)13-22(11-20)33-5)19-6-7-23-24(12-19)29-25(15-27-23)18-14-28-30(3)16-18/h6-7,10-17,26H,8-9H2,1-5H3
comment: Erdafitinib is a pan-fibroblast growth factor receptor (FGFRs 1-4) tyrosine kinase inhibitor <Reference id=37611/><Reference id=30632/><Reference id=37608/>. It is the first targeted drug to be approved for advanced bladder cancer.
iupac name: N'-(3,5-dimethoxyphenyl)-N'-[3-(1-methylpyrazol-4-yl)quinoxalin-6-yl]-N-propan-2-ylethane-1,2-diamine
synonym: JNJ 42756493
synonym: JNJ42756493
synonym: JNJ-42756493
synonym: compound 4 [WO2011135376]
synonym: Balversa®
approved: t
ligand name: erdafitinib
type: SyntheticOrganicLigand

PF-04859989
canonical SMILES: O=C1C(N)Cc2c(N1O)cccc2
isomeric SMILES: O=C1[C@@H](N)Cc2c(N1O)cccc2
in ch i key: HYTRYTZFJVVZAF-ZETCQYMHSA-N
in ch i: InChI=1S/C9H10N2O2/c10-7-5-6-3-1-2-4-8(6)11(13)9(7)12/h1-4,7,13H,5,10H2/t7-/m0/s1
comment: PF-04859989 was identified as a potent, irreversable and selective inhibitor of human and rat kynurenine aminotransferase II (KATII; a.k.a. aminoadipate aminotransferase AADAT) <Reference id=30634/><Reference id=30635/> . An X-ray crystal structure of the enzyme co-crystalised with an inhibitor has been reported <Reference id=30634/>. In vivo pharmacokinetic and efficacy studies in rat show it to be brain-penetrant, reducing brain kynurenic acid by 50%. KAT inhibitors are expected to exhibit neuroprotective effects, that may be beneficial for the treatment of neurodegenerative and cognitive impairment disorders <Reference id=34412/>.
iupac name: (3S)-3-amino-1-hydroxy-3,4-dihydroquinolin-2-one
xref: CHEMBL2047851
synonym: compound 1 [PMID: 23466229]
approved: f
ligand name: PF-04859989
type: SyntheticOrganicLigand

SP-4206
in ch i key: VNZHOIDQBPFEJU-OAQYLSRUSA-N
comment: SP-4206 is a small molecule protein-protein interaction inhibitor. It binds IL-2 and prevents its interaction with the IL-2 receptor α <Reference id=30621/><Reference id=30623/>. The X-ray structure of SP-4206 bound to a dynamic hot spot on IL-2 is presented with PDB identifier 1PY2 <Reference id=30622/>.
iupac name: 5-[[2,3-dichloro-4-[5-[1-[2-[[(2R)-2-(diaminomethylideneamino)-4-methylpentanoyl]amino]acetyl]piperidin-4-yl]-1-methylpyrazol-3-yl]phenoxy]methyl]furan-2-carboxylic acid
xref: CHEMBL429852
synonym: SP4206
synonym: compound 13 [PMID:12656598]
approved: f
ligand name: SP-4206
type: SyntheticOrganicLigand

resatorvid
in ch i key: LEEIJTHMHDMWLJ-CQSZACIVSA-N
comment: Resatorvid (TAK242) was first identified as an inhibitor of inflammatory mediator production in LPS treated mouse macrophages <Reference id=30617/>. Subsequent work found that this action was attributable to the compound's activity as a Toll-like receptor 4 (TLR4) antagonist <Reference id=30618/>.
iupac name: ethyl (6R)-6-[(2-chloro-4-fluorophenyl)sulfamoyl]cyclohexene-1-carboxylate
xref: CHEMBL225157
synonym: TAK242
synonym: TAK 242
synonym: TAK-242
approved: f
ligand name: resatorvid
type: SyntheticOrganicLigand

belnacasan
in ch i key: SJDDOCKBXFJEJB-MOKWFATOSA-N
in ch i: InChI=1S/C24H33ClN4O6/c1-5-34-23-16(12-18(30)35-23)27-21(32)17-7-6-10-29(17)22(33)19(24(2,3)4)28-20(31)13-8-9-15(26)14(25)11-13/h8-9,11,16-17,19,23H,5-7,10,12,26H2,1-4H3,(H,27,32)(H,28,31)/t16-,17-,19+,23+/m0/s1
comment: Belnacasan is a prodrug of <Ligand id=9034/>, a caspase-1 inhibitor that was developed by Vertex. Pharmacological inhibition of caspase-1 is being investigated as a mechanism to reduce pro-inflammatory cytokine (predominantly IL-1β) production as a novel treatment of inflammatory diseases <Reference id=30603/>. Inhibition of caspase-1 is a small molecule strategy developed as an alternative to the use of anti-IL-1β neutralising antibodies, such as <Ligand id=6773/>, or the dimeric fusion protein <Ligand id=6790/> that acts as a IL-1 trap.
iupac name: (2S)-1-[(2S)-2-[(4-amino-3-chlorobenzoyl)amino]-3,3-dimethylbutanoyl]-N-[(2R,3S)-2-ethoxy-5-oxooxolan-3-yl]pyrrolidine-2-carboxamide
synonym: HMR3480
synonym: VX-765
approved: f
ligand name: belnacasan
type: SyntheticOrganicLigand

VRT-043198
in ch i key: SOZONDBMOYWSRW-QANKJYHBSA-N
in ch i: InChI=1S/C22H29ClN4O6/c1-22(2,3)18(26-19(31)12-6-7-15(24)14(23)9-12)21(33)27-8-4-5-16(27)20(32)25-13(11-28)10-17(29)30/h6-7,9,11,13,16,18H,4-5,8,10,24H2,1-3H3,(H,25,32)(H,26,31)(H,29,30)/t13-,16-,18+/m0/s1
comment: VRT-043198 generated from the prodrug <Ligand id=9035/> (VX-765) is a potent and selective inhibitor of caspase-1 from Vertex. When administered orally to mice, it inhibits lipopolysaccharide-induced cytokine secretion and reduces disease severity and the expression of inflammatory mediators in models of rheumatoid arthritis and skin inflammation, suggesting that as a cytokine inhibitor it could be useful for treatment of inflammatory diseases <Reference id=30603/>.
approved: f
ligand name: VRT-043198
type: SyntheticOrganicLigand

PSB-6426
in ch i key: AEVBPXDFDKBGLT-YOUFYPILSA-N
in ch i: InChI=1S/C22H29N4O10P/c1-3-34-37(33,35-4-2)12-13-5-7-14(8-6-13)24-16(28)11-23-20(31)19-17(29)18(30)21(36-19)26-10-9-15(27)25-22(26)32/h5-10,17-19,21,29-30H,3-4,11-12H2,1-2H3,(H,23,31)(H,24,28)(H,25,27,32)/t17-,18+,19-,21+/m0/s1
comment: PSB-6426 is a tool compound which inhibits ectonucleoside triphosphate diphosphohydrolase 2 (ENTPD2, CD39L1) <Reference id=30597/>. Structurally it is a uridine derivative, and it was the most potent compound discovered in a series designed to find novel structures with potential cardioprotective action.
iupac name: (2S,3S,4R,5R)-N-[2-[4-(diethoxyphosphorylmethyl)anilino]-2-oxoethyl]-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolane-2-carboxamide
xref: CHEMBL469212
synonym: compound 19a [PMID: 18630897]
approved: f
ligand name: PSB-6426
type: SyntheticOrganicLigand

INCB8761
in ch i key: ZNSVOHSYDRPBGI-CBQRAPNFSA-N
in ch i: InChI=1S/C29H31F3N6O3/c30-29(31,32)21-4-1-3-19(15-21)27(40)36-17-25(39)38-14-9-23(18-38)37-22-7-10-28(41,11-8-22)24-6-5-20(16-35-24)26-33-12-2-13-34-26/h1-6,12-13,15-16,22-23,37,41H,7-11,14,17-18H2,(H,36,40)/t22?,23-,28?/m0/s1
comment: INCB8761 is a CCR2 antagonist. Pharmacological targeting of the CCL2/CCR2 axis is predicted to be an effective immunotherapeutic strategy to reduce the inflammatory monocyte recruitment which appears to underlie pancreatic cancer progression <Reference id=30599/>.
iupac name: N-[2-[(3S)-3-[[4-hydroxy-4-(5-pyrimidin-2-ylpyridin-2-yl)cyclohexyl]amino]pyrrolidin-1-yl]-2-oxoethyl]-3-(trifluoromethyl)benzamide
xref: CHEMBL2029422
synonym: PF-4136309
synonym: PF4136309
synonym: INCB-8761
synonym: compound 17 [PMID: 24900280]
approved: f
ligand name: INCB8761
type: SyntheticOrganicLigand

ONX-0914
in ch i key: WQAVPPWWLLVGFK-VTNASVEKSA-N
in ch i: InChI=1S/C31H40N4O7/c1-21(32-27(36)19-35-13-15-41-16-14-35)29(38)34-26(18-23-9-11-24(40-3)12-10-23)30(39)33-25(28(37)31(2)20-42-31)17-22-7-5-4-6-8-22/h4-12,21,25-26H,13-20H2,1-3H3,(H,32,36)(H,33,39)(H,34,38)/t21-,25-,26-,31+/m0/s1
comment: Proteolix (later Onyx Pharmaceuticals, now Amgen) developed the peptidomimetic inhibitor PR-957 (ONX-0914), which selectively inhibited the chymotrypsin-like activity of LMP7. This blocked presentation of LMP7-specific, MHC-I-restricted antigens and reduced immunoproteasome production of pro-inflammatory cytokines such as IL-6, IFN-γ, TNF-α and IL-23 <Reference id=30598/>. Note there are at least 6 isomeric alternatives for this structure including ChEMBL entries and SureChEMBL patent mappings (see %22same connectivity%22 links in the PubChem CID entry).
synonym: PR-957
approved: f
ligand name: ONX-0914
type: SyntheticOrganicLigand

ARL 67156
in ch i key: ILXFKEOLRYLPJG-IDTAVKCVSA-N
comment: ARL 67156 is a research compound used experimantally as the trisodium salt PubChem CID 11957464). It is an inhibitor of ecto-ATPase activity. Structurally, ARL 67156 is an analogue of ATP and therefore competes with substrate at the enzyme.
iupac name: [dibromo-[[[(2R,3S,4R,5R)-5-(6-diethylaminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl]methyl]phosphonic acid
xref: CHEMBL1206141
synonym: ARL-67156
synonym: FPL-67156
synonym: FPL 67156
synonym: 6-N,N-diethyl-beta,gamma-dibromomethylene-D-ATP
approved: f
ligand name: ARL 67156
type: SyntheticOrganicLigand

mometasone
in ch i key: QLIIKPVHVRXHRI-CXSFZGCWSA-N
in ch i: InChI=1S/C22H28Cl2O4/c1-12-8-16-15-5-4-13-9-14(25)6-7-19(13,2)21(15,24)17(26)10-20(16,3)22(12,28)18(27)11-23/h6-7,9,12,15-17,26,28H,4-5,8,10-11H2,1-3H3/t12-,15+,16+,17+,19+,20+,21+,22+/m1/s1
comment: Mometasone is a corticosteroid anti-inflammatory drug.
iupac name: (8S,9R,10S,11S,13S,14S,16R,17R)-9-chloro-17-(2-chloroacetyl)-11,17-dihydroxy-10,13,16-trimethyl-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-3-one
xref: CHEMBL1201404
synonym: Nasonex®
synonym: Elocon® (topical)
approved: t
ligand name: mometasone
type: SyntheticOrganicLigand

3beta-Hydroxy-20(29)-lupene
in ch i key: MQYXUWHLBZFQQO-HQBMYVNCSA-N
in ch i: InChI=1S/C30H50O/c1-19(2)20-11-14-27(5)17-18-29(7)21(25(20)27)9-10-23-28(6)15-13-24(31)26(3,4)22(28)12-16-30(23,29)8/h20-25,31H,1,9-18H2,2-8H3/t20?,21?,22-,23?,24?,25+,27?,28?,29+,30?/m0/s1
comment: Oral administration of Lupeol to dextran sulfate sodium (DSS)-induced colitis mice reduced intestinal inflammation and increased survival. This was associated with decreased expression of M1-related genes and increased expression of M2-related genes. Lupeol ameliorates experimental inflammatory bowel disease, at least in part, through inhibiting M1 and promoting M2 macrophages <Reference id=30593/>. Similar results were simultaneously published in a different journal <Reference id=30594/>. Note there are many isomers of this structure that can be found using the %22same connectivity%22 operator in the PubChem CID entry.
iupac name: (5aR,7aR,13bR)-3a,5a,5b,8,8,11a-hexamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysen-9-ol
synonym: Lupeol
synonym: Fagarasterol
approved: f
ligand name: 3beta-Hydroxy-20(29)-lupene
type: SyntheticOrganicLigand

L6H21
canonical SMILES: COc1ccc(cc1)C(=O)C=Cc1cccc(c1OC)OC
isomeric SMILES: COc1ccc(cc1)C(=O)/C=C/c1cccc(c1OC)OC
in ch i key: IECVLMVZGCYCSZ-FMIVXFBMSA-N
in ch i: InChI=1S/C18H18O4/c1-20-15-10-7-13(8-11-15)16(19)12-9-14-5-4-6-17(21-2)18(14)22-3/h4-12H,1-3H3/b12-9+
comment: Bnding affinity of L6H21 to MD-2 protein was analysed and effects on MAPK and NF-κB signalling were determined. Anti-inflammatory effects were evaluated in septic C57BL/6 mice. Results imply L6H21 has potential for treatment of sepsis and MD-2 (LY96) is an important therapeutic target for inflammatory disorders <Reference id=30592/>.
iupac name: (E)-3-(2,3-dimethoxyphenyl)-1-(4-methoxyphenyl)prop-2-en-1-one
xref: CHEMBL2013139
approved: f
ligand name: L6H21
type: SyntheticOrganicLigand

motolimod
in ch i key: QSPOQCXMGPDIHI-UHFFFAOYSA-N
in ch i: InChI=1S/C28H34N4O2/c1-3-13-31(14-4-2)28(34)24-17-23-12-11-22(18-25(23)30-26(29)19-24)20-7-9-21(10-8-20)27(33)32-15-5-6-16-32/h7-12,17-18H,3-6,13-16,19H2,1-2H3,(H2,29,30)
comment: Motolimod is an investigational Toll-like receptor 8 (TLR8) agonist <Reference id=30591/>.
iupac name: 2-amino-N,N-dipropyl-8-[4-(pyrrolidine-1-carbonyl)phenyl]-3H-1-benzazepine-4-carboxamide
xref: CHEMBL3301618
synonym: VTX-2337
approved: f
ligand name: motolimod
type: SyntheticOrganicLigand

852A
canonical SMILES: CCc1nc2c(n1CCCCNS(=O)(=O)C)c1ccccc1nc2N
isomeric SMILES: CCc1nc2c(n1CCCCNS(=O)(=O)C)c1ccccc1nc2N
in ch i key: YZOQZEXYFLXNKA-UHFFFAOYSA-N
in ch i: InChI=1S/C17H23N5O2S/c1-3-14-21-15-16(12-8-4-5-9-13(12)20-17(15)18)22(14)11-7-6-10-19-25(2,23)24/h4-5,8-9,19H,3,6-7,10-11H2,1-2H3,(H2,18,20)
comment: 852A is a soluble agonist of Toll-like receptor 7 (TLR7) <Reference id=30585/>. It has been clinically investigated for potential anti-cancer activity <Reference id=30586/><Reference id=30587/><Reference id=30588/><Reference id=30589/><Reference id=36715/>.
iupac name: N-[4-(4-amino-2-ethylimidazo[4,5-c]quinolin-1-yl)butyl]methanesulfonamide
xref: CHEMBL549344
approved: f
ligand name: 852A
type: SyntheticOrganicLigand

defoslimod
in ch i key: GOWLTLODGKPXMN-MEKRSRHXSA-N
comment: Defoslimod is an analogue of lipopolysaccharide endotoxin-derived lipid A obtained from E. coli <Reference id=30582/>. It was developed as an immunotherapeutic agent for the treatment of cancer. Defoslimod acts as an agonist of Toll-like receptors 2 and 4 (TLR2 and TLR4) <Reference id=30584/>. We show the structure with chemical formula provided in the INN record for the compound (C52H100N2O20P2). PubChem CID 56841121, which claims to represent defoslimod has an extra carbon atom and two associated hydrogens (C53H102N2O20P2). But note also that the structure reported in <Reference id=30582/> only has 51 carbon atoms.
xref: CHEMBL2105854
synonym: OM 174
synonym: OM-174
approved: f
ligand name: defoslimod
type: NaturalProductLigand

A-196
canonical SMILES: Clc1cc2c(nnc(c2cc1Cl)NC1CCCC1)c1ccncc1
isomeric SMILES: Clc1cc2c(nnc(c2cc1Cl)NC1CCCC1)c1ccncc1
in ch i key: ABGOSOMRWSYAOB-UHFFFAOYSA-N
in ch i: InChI=1S/C18H16Cl2N4/c19-15-9-13-14(10-16(15)20)18(22-12-3-1-2-4-12)24-23-17(13)11-5-7-21-8-6-11/h5-10,12H,1-4H2,(H,22,24)
comment: A-196 is a selective chemical probe for the methyltransferases suppressor of variegation 4-20 homologs 1 and 2 (SUV420H1 and SUV420H2), and is one of the compounds available from the Structural Genomics Consortium's epigenetic probes set. It was developed in collaboration with AbbVie. SUV420H1 and SUV420H2 are responsible for di- and tri-methylating lysine 20 of histone H4 (H4K20).
iupac name: 6,7-dichloro-N-cyclopentyl-4-(pyridin-4-yl)phthalazin-1-amine
approved: f
ligand name: A-196
type: SyntheticOrganicLigand

PSB-0963
in ch i key: JXFRJOYKTCEJDG-UHFFFAOYSA-M
in ch i: InChI=1S/C28H18N2O5S/c29-26-23(36(33,34)35)14-22(24-25(26)28(32)21-8-4-3-7-20(21)27(24)31)30-19-10-9-17-11-15-5-1-2-6-16(15)12-18(17)13-19/h1-14,30H,29H2,(H,33,34,35)/p-1
comment: PSB-0963 is a research compound which primarily inhibits ecto-5'-nucleotidase (NTE5, CD73), but also inhibits ectonucleoside triphosphate diphosphohydrolase 1 (ENTPD1; CD39) <Reference id=30577/>. It is compound 52 in <Reference id=30577/>. The sodium salt is used experimentally.
iupac name: 1-amino-4-(anthracen-2-ylamino)-9,10-dioxoanthracene-2-sulfonate
xref: CHEMBL608559
approved: f
ligand name: PSB-0963
type: SyntheticOrganicLigand

GW791343
in ch i key: GRUWKTIRBBPZSD-UHFFFAOYSA-N
in ch i: InChI=1S/C20H24F2N4O/c1-14-2-3-15(13-26-8-6-23-7-9-26)10-19(14)25-20(27)12-24-16-4-5-17(21)18(22)11-16/h2-5,10-11,23-24H,6-9,12-13H2,1H3,(H,25,27)
comment: GW791343 is an negative allosteric modulator of the human P2X7 receptor, but is a positive modulator of the rat orthologue <Reference id=30572/>. Mutational studies suggest that amino acid 95 is a key residue in determining the species difference in antagonist effects <Reference id=30573/>. The position 95 residue is phenylalanine in human P2X7 receptors, and leucine in rat.
iupac name: 2-[(3,4-difluorophenyl)amino]-N-[2-methyl-5-(piperazin-1-ylmethyl)phenyl]acetamide
xref: CHEMBL3186981
synonym: GW-791343
approved: f
ligand name: GW791343
type: SyntheticOrganicLigand

AZ10606120
in ch i key: FQMZXMVHHKXGTM-UHFFFAOYSA-N
in ch i: InChI=1S/C25H34N4O2/c30-9-8-26-6-7-27-23-5-4-20-21(28-23)2-1-3-22(20)29-24(31)16-25-13-17-10-18(14-25)12-19(11-17)15-25/h1-5,17-19,26,30H,6-16H2,(H,27,28)(H,29,31)
comment: AZ10606120 is a negative allosteric modulator of the human P2X7 receptor <Reference id=30572/><Reference id=30573/>. As a research compound AZ10606120 is being studied for its potential antineoplastic activity <Reference id=30574/>.
iupac name: 2-(1-adamantyl)-N-[2-[2-(2-hydroxyethylamino)ethylamino]quinolin-5-yl]acetamide
xref: CHEMBL562308
synonym: AZ-10606120
synonym: AZ 10606120
synonym: compound-17 [PMID: 18071294]
synonym: compound 43 [PMID: 19191585]
approved: f
ligand name: AZ10606120
type: SyntheticOrganicLigand

AT38
canonical SMILES: O=C(c1ccccc1O)OCc1no[n+](c1C(=O)N)[O-]
isomeric SMILES: O=C(c1ccccc1O)OCc1no[n+](c1C(=O)N)[O-]
in ch i key: YWHHKFGUOITYRD-UHFFFAOYSA-N
in ch i: InChI=1S/C11H9N3O6/c12-10(16)9-7(13-20-14(9)18)5-19-11(17)6-3-1-2-4-8(6)15/h1-4,15H,5H2,(H2,12,16)
comment: AT38 is a salicylate hydrolysed from a soluble furoxan derivative MC526 (see patent WO2011104671 A1 <Reference id=30571/>). AT38 inhibits metabolic pathways involved in the development of tumours, which underlies the compound's potential therapeutic antitumour activity <Reference id=30570/>.
iupac name: (4-carbamoyl-5-oxido-1,2,5-oxadiazol-5-ium-3-yl)methyl 2-hydroxybenzoate
synonym: [3-(aminocarbonyl)furoxan-4-yl]methyl salicylate
approved: f
ligand name: AT38
type: SyntheticOrganicLigand

navoximod
canonical SMILES: OC(C1CCCCC1)CC1c2ccccc2c2n1cnc2
isomeric SMILES: OC(C1CCCCC1)CC1c2ccccc2c2n1cnc2
in ch i key: YTRRAUACYORZLX-UHFFFAOYSA-N
in ch i: InChI=1S/C18H22N2O/c21-18(13-6-2-1-3-7-13)10-16-14-8-4-5-9-15(14)17-11-19-12-20(16)17/h4-5,8-9,11-13,16,18,21H,1-3,6-7,10H2
comment: Navoximod (NLG-919) is a potent inhibitor of indoleamine-2,3-dioxygenase (IDO1) that was developed by Genentech and NewLink Genetics <Reference id=37927/><Reference id=38078/>. IOD1 is the first and rate-limiting component of the pathway mediating metabolism of tryptophan to kynurenine. Tryptophan depletion enhances the number and function of the Treg (suppressive) arm of the immune system and inhibits the effector T cell (stimulatory) arm. This action of IDO1 facilitates acquired local and peripheral immune tolerance in normal and pathological conditions. IOD1 inhibitors are being developed as novel therapeutics to reverse the immunosuppression associated with cancer. The crystal structure of human IDO1 in complex with navoximod has been submitted to the PDB with ID 6O3I <Reference id=38078/>.
iupac name: 1-cyclohexyl-2-(5H-imidazo[5,1-a]isoindol-5-yl)ethanol
xref: CHEMBL3629569
synonym: NLG919
synonym: GDC-0919
synonym: RG6078
synonym: NLG 919
synonym: NLG-919
approved: f
ligand name: navoximod
type: SyntheticOrganicLigand

NCX-4016
canonical SMILES: [O-][N+](=O)OCc1cccc(c1)OC(=O)c1ccccc1OC(=O)C
isomeric SMILES: [O-][N+](=O)OCc1cccc(c1)OC(=O)c1ccccc1OC(=O)C
in ch i key: IOJUJUOXKXMJNF-UHFFFAOYSA-N
in ch i: InChI=1S/C16H13NO7/c1-11(18)23-15-8-3-2-7-14(15)16(19)24-13-6-4-5-12(9-13)10-22-17(20)21/h2-9H,10H2,1H3
comment: NCX-4016 is an inhibitor which supports generation of reactive oxygen species (ROS) that modify CCL2 levels, disabling T cell chemotaxis. It is expected that this type of action will have anti-inflammatory, antiproliferative, and cytoprotective activity <Reference id=30567/>. NCX-4016 is a NO-NSAID type compound (nitric oxide-donating NSAID), a hybrid nitrate conjugated to an NSAID, in this case <Ligand id=4139/>. This type of compound was designed to exploit the gastroprotective properties of NO bioactivity, to combat the gastrotoxicity which compromises NSAID use <Reference id=30566/>.
iupac name: [3-(nitrooxymethyl)phenyl] 2-acetyloxybenzoate
xref: CHEMBL374385
synonym: nitric oxide-releasing aspirin
synonym: nitroaspirin
synonym: NCX 4016
synonym: NCX4016
approved: f
ligand name: NCX-4016
type: SyntheticOrganicLigand

LM10
canonical SMILES: Fc1ccc2c(c1)[nH]cc2C=Cc1nnn[nH]1
isomeric SMILES: Fc1ccc2c(c1)[nH]cc2/C=C/c1nnn[nH]1
in ch i key: JDBSZVDIUIRSDG-DAFODLJHSA-N
in ch i: InChI=1S/C11H8FN5/c12-8-2-3-9-7(6-13-10(9)5-8)1-4-11-14-16-17-15-11/h1-6,13H,(H,14,15,16,17)/b4-1+
comment: LM10 is an experimental compound reported as an inhibitor of tryptophan 2,3-dioxygenase (TDO2), with anti-neoplastic activity in a murine syngeneic tumour model <Reference id=30562/><Reference id=30563/>. The closest structural match on PubChem (CID 91885138) is an alternative representation, with different double bond specification across the vinyl group linking the indole and tetrazole groups.
iupac name: 6-fluoro-3-[(E)-2-(1H-1,2,3,4-tetrazol-5-yl)ethenyl]-1H-indole
xref: CHEMBL1812545
synonym: LM-10
approved: f
ligand name: LM10
type: SyntheticOrganicLigand

acenocoumarol
in ch i key: VABCILAOYCMVPS-UHFFFAOYSA-N
in ch i: InChI=1S/C19H15NO6/c1-11(21)10-15(12-6-8-13(9-7-12)20(24)25)17-18(22)14-4-2-3-5-16(14)26-19(17)23/h2-9,15,22H,10H2,1H3
comment: Acenocoumarol is a coumarin that is used as an anticoagulant, with actions and uses similar to <Ligand id=6853/>. The coumarins are vitamin K epoxide reductase antagonists.
iupac name: 4-hydroxy-3-[1-(4-nitrophenyl)-3-oxobutyl]chromen-2-one
xref: CHEMBL397420
synonym: Sinthrome®
synonym: Sintrom®
approved: t
ligand name: acenocoumarol
type: SyntheticOrganicLigand

PF-152
in ch i key: SKEAGJWUKCNICJ-LSDHHAIUSA-N
in ch i: InChI=1S/C21H24FN7O5/c1-12-24-17(20-26-28-29(27-20)8-14-10-34-15(9-30)11-33-14)6-18(25-12)21(31)23-7-13-3-4-16(22)19(5-13)32-2/h3-6,14-15,30H,7-11H2,1-2H3,(H,23,31)/t14-,15+/m0/s1
comment: PF-152 is a matrix metalloproteinase-13 (MMP13) inhibitor <Reference id=30511/>, with potential to treat osteoarthritis.
iupac name: N-[(4-fluoro-3-methoxyphenyl)methyl]-6-[2-[[(2S,5R)-5-(hydroxymethyl)-1,4-dioxan-2-yl]methyl]tetrazol-5-yl]-2-methylpyrimidine-4-carboxamide
synonym: example 64 [WO2009016498]
synonym: compound 43a
synonym: PF152
approved: f
ligand name: PF-152
type: SyntheticOrganicLigand

compound 19y [Kiss et al., 2011]
in ch i key: NLWUQNVDUOHGIP-UHFFFAOYSA-N
in ch i: InChI=1S/C14H9ClN2O5/c15-8-1-4-10(5-2-8)21-13-16-17(14(20)22-13)9-3-6-11(18)12(19)7-9/h1-7,18-19H
comment: Compound 19y is one of a series of derivatives synthesised and tested by a group from BIAL-Portela & Ca, SA, as inhibitors of fatty acid amide hydrolase (FAAH) <Reference id=30509/>. BIAL-Portela were responsible for the development of <Ligand id=9001/>, another FAAH inhibitor that caused serious adverse events in a Phase I clinical trial in January 2016.
iupac name: 5-(4-chlorophenoxy)-3-(3,4-dihydroxyphenyl)-1,3,4-oxadiazol-2-one
xref: CHEMBL3218814
approved: f
ligand name: compound 19y [Kiss et al., 2011]
type: SyntheticOrganicLigand

JNJ-42165279
in ch i key: YWGYNGCRVZLMCS-UHFFFAOYSA-N
comment: JNJ-42165279 is an investigational, covalent and selective inhibitor of fatty acid amide hydrolase (FAAH) <Reference id=30505/>. Preclinical test findings are reported in <Reference id=30506/>, with the conclusion that the favourable ADME and pharmacodynamic profiles of JNJ-42165279 supported it being progressed to clinical trial.
iupac name: N-(4-chloropyridin-3-yl)-4-[(2,2-difluoro-1,3-benzodioxol-5-yl)methyl]piperazine-1-carboxamide
synonym: JNJ42165279
synonym: Example 1 [WO2011139951 A1]
approved: f
ligand name: JNJ-42165279
type: SyntheticOrganicLigand

mebeverine
in ch i key: VYVKHNNGDFVQGA-UHFFFAOYSA-N
in ch i: InChI=1S/C25H35NO5/c1-6-26(19(2)17-20-9-12-22(28-3)13-10-20)15-7-8-16-31-25(27)21-11-14-23(29-4)24(18-21)30-5/h9-14,18-19H,6-8,15-17H2,1-5H3
comment: Mebeverine is a musculotropic antispasmodic drug. Marketed formulations contain the hydrochloride salt (PubChem CID 17683) which is sometimes combined with ispaghula husk (sold as Fybogel®) to add fibre to the gut contents.
iupac name: 4-[ethyl-[1-(4-methoxyphenyl)propan-2-yl]amino]butyl 3,4-dimethoxybenzoate
xref: CHEMBL282121
synonym: Colofac®
synonym: Duspatalin®
synonym: CSAG-144
approved: t
ligand name: mebeverine
type: SyntheticOrganicLigand

compound NRA 4 [PMID: 25262941]
canonical SMILES: Brc1ccc(c(c1)c1oc2ccccc2c(=O)c1O)F
isomeric SMILES: Brc1ccc(c(c1)c1oc2ccccc2c(=O)c1O)F
in ch i key: OGIJEXWCHFAYRS-UHFFFAOYSA-N
in ch i: InChI=1S/C15H8BrFO3/c16-8-5-6-11(17)10(7-8)15-14(19)13(18)9-3-1-2-4-12(9)20-15/h1-7,19H
comment: compound NRA 4 is a neuromedin U receptor 2 (NMUR2) agonist.
iupac name: 2-(5-bromo-2-fluorophenyl)-3-hydroxy-4H-chromen-4-one
approved: f
ligand name: compound NRA 4 [PMID: 25262941]
type: SyntheticOrganicLigand

NM4-C16
in ch i key: GDPUTCQTCXMCTL-YPQIROLXSA-N
comment: NM4-C16 is a dual neuromedin U receptor 1 (NMUR1)/neuromedin U receptor 2 (NMUR2) agonist.
iupac name: 2-[(2S)-5-carbamimidamido-2-({1-[(2S)-5-carbamimidamido-2-{2-[(2S)-2-(2-{2-[6-(dihexadecylamino)hexanamido]-2-methylpropanamido}-3-phenylpropanamido)-4-methylpentanamido]-3-phenylpropanamido}pentanoyl]pyrrolidin-2-yl}formamido)pentanamido]butanediamide
approved: f
ligand name: NM4-C16
type: PeptideLigand

compound 1 [WO2014017936]
in ch i key: SXKWDPMBWTZYCA-UHFFFAOYSA-N
in ch i: InChI=1S/C17H21N5O2/c1-21(14-7-2-3-8-14)17(24)22-10-15(19-11-22)12-5-4-6-13(9-12)20-16(18)23/h4-6,9-11,14H,2-3,7-8H2,1H3,(H3,18,20,23)
comment: This structure was the initial guess for BIA 10-2474 inhibitor of fattty acid amide hydrolase (FAAH), on the basis of process patents <Reference id=30420/> and <Reference id=30421/>.
iupac name: 4-[3-(carbamoylamino)phenyl]-N-cyclopentyl-N-methylimidazole-1-carboxamide
approved: f
ligand name: compound 1 [WO2014017936]
type: SyntheticOrganicLigand

PETCM
canonical SMILES: OC(C(Cl)(Cl)Cl)Cc1ccncc1
isomeric SMILES: OC(C(Cl)(Cl)Cl)Cc1ccncc1
in ch i key: NGTDJJKTGRNNAU-UHFFFAOYSA-N
in ch i: InChI=1S/C8H8Cl3NO/c9-8(10,11)7(13)5-6-1-3-12-4-2-6/h1-4,7,13H,5H2
iupac name: 1,1,1-trichloro-3-(pyridin-4-yl)propan-2-ol
synonym: 1-(trichloromethyl)-2-(4-pyridine)ethanol
approved: f
ligand name: PETCM
type: SyntheticOrganicLigand

compound 5d [PMID: 25815150]
in ch i key: TZCCKCLHNUSAMQ-DUGSHLAESA-N
comment: Compound 5d is a neuromedin U receptor 1 (NMUR1) agonist.
approved: f
ligand name: compound 5d [PMID: 25815150]
type: PeptideLigand

GSK180
canonical SMILES: OC(=O)CCn1c(=O)oc2c1cc(Cl)c(c2)Cl
isomeric SMILES: OC(=O)CCn1c(=O)oc2c1cc(Cl)c(c2)Cl
in ch i key: MIGAKMWKMLYGJX-UHFFFAOYSA-N
in ch i: InChI=1S/C10H7Cl2NO4/c11-5-3-7-8(4-6(5)12)17-10(16)13(7)2-1-9(14)15/h3-4H,1-2H2,(H,14,15)
comment: GSK180 is a potent and selective competitive inhibitor of kynurenine 3-monooxygenase (KMO) <Reference id=30503/>, an enzyme involved in tryptophan metabolism. The structure is a derivative of the enzyme substrate kynurenine. Currently the only X-ray crystal structure available is for GSK180 in complex with the Pseudomonas fluorescens KMO homologue (PDB ID 5FN0).
iupac name: 3-(5,6-dichloro-2-oxo-1,3-benzoxazol-3-yl)propanoic acid
synonym: inhibitor A1 [PMID: 28604669]
approved: f
ligand name: GSK180
type: SyntheticOrganicLigand

UFP-512
in ch i key: USVQTDLSVBRMCR-YGPDHOBYSA-N
in ch i: InChI=1S/C31H33N5O5/c1-17-11-21(37)12-18(2)22(17)14-23(32)31(41)36-16-20-8-4-3-7-19(20)13-27(36)30(40)35-26(15-28(38)39)29-33-24-9-5-6-10-25(24)34-29/h3-12,23,26-27,37H,13-16,32H2,1-2H3,(H,33,34)(H,35,40)(H,38,39)/t23-,26-,27-/m0/s1
comment: UFP-512 is a selective δ opioid receptor agonist, with anxiolytic- and antidepressant-like activities in mice <Reference id=30496/>.
iupac name: (3S)-3-[[(3S)-2-[(2S)-2-amino-3-(4-hydroxy-2,6-dimethylphenyl)propanoyl]3,4-dihydro-1H-isoquinoline-3-carbonyl]amino]-3-(1H-benzimidazol-2-yl)propanoic acid
xref: CHEMBL442577
synonym: H-Dmt-Tic-NH-CH(CH2-COOH)-Bid
approved: f
ligand name: UFP-512
type: SyntheticOrganicLigand

AR-M1000390
in ch i key: SMUGAZNLKPFBSB-UHFFFAOYSA-N
in ch i: InChI=1S/C23H28N2O/c1-3-25(4-2)23(26)21-12-10-19(11-13-21)22(18-8-6-5-7-9-18)20-14-16-24-17-15-20/h5-13,24H,3-4,14-17H2,1-2H3
comment: AR-M1000390 is a nonpeptidic δ receptor selective agonist <Reference id=30494/>.
iupac name: N,N-diethyl-4-(phenyl-piperidin-4-ylidenemethyl)benzamide
xref: CHEMBL415521
synonym: ARM-390
synonym: AR-M390
approved: f
ligand name: AR-M1000390
type: SyntheticOrganicLigand

ADL5859
in ch i key: OPIKUXLJQFYMSC-UHFFFAOYSA-N
in ch i: InChI=1S/C24H28N2O3/c1-3-26(4-2)23(28)18-10-8-17(9-11-18)19-16-24(12-14-25-15-13-24)29-21-7-5-6-20(27)22(19)21/h5-11,16,25,27H,3-4,12-15H2,1-2H3
comment: ADL5859 is a potent, orally bioavailable δ opioid receptor agonist <Reference id=30484/>.
iupac name: N,N-diethyl-4-(5-hydroxyspiro[chromene-2,4'-piperidine]-4-yl)benzamide
xref: CHEMBL494480
synonym: ADL 5859
synonym: ADL-5859
synonym: compound 20 [PMID: 18788723]
approved: f
ligand name: ADL5859
type: SyntheticOrganicLigand

ADL5747
in ch i key: ALGHKWSXJUQNJJ-UHFFFAOYSA-N
in ch i: InChI=1S/C24H28N2O3/c1-3-26(4-2)23(28)17-9-10-18(21(27)15-17)20-16-24(11-13-25-14-12-24)29-22-8-6-5-7-19(20)22/h5-10,15-16,25,27H,3-4,11-14H2,1-2H3
comment: ADL5747 is a selective, nonpeptidic δ opioid receptor agonist <Reference id=30486/>. Due to its favorable efficacy, safety, and pharmacokinetic profile ADL5747 was progressed as a clinical candidate for the treatment of pain.
iupac name: N,N-diethyl-3-hydroxy-4-spiro[chromene-2,4'-piperidine]-4-ylbenzamide
xref: CHEMBL561339
synonym: ADL-5747
synonym: ADL 5747
synonym: compound 36 [PMID: 19694468]
approved: f
ligand name: ADL5747
type: SyntheticOrganicLigand

BW373U86
in ch i key: LBLDMHBSVIVJPM-YZIHRLCOSA-N
in ch i: InChI=1S/C27H37N3O2/c1-6-16-29-18-21(5)30(19-20(29)4)26(24-10-9-11-25(31)17-24)22-12-14-23(15-13-22)27(32)28(7-2)8-3/h6,9-15,17,20-21,26,31H,1,7-8,16,18-19H2,2-5H3/t20-,21+,26-/m1/s1
comment: BW373U86 is a potent and selective nonpeptidic δ opioid receptor agonist <Reference id=30483/>.
iupac name: 4-[(R)-[(2S,5R)-2,5-dimethyl-4-prop-2-enylpiperazin-1-yl]-(3-hydroxyphenyl)methyl]-N,N-diethylbenzamide
xref: CHEMBL25230
synonym: BW 373U86
synonym: BW-373U86
synonym: SNC-86
approved: f
ligand name: BW373U86
type: SyntheticOrganicLigand

BIA 10-2474
canonical SMILES: [O-][n+]1cccc(c1)c1ncn(c1)C(=O)N(C1CCCCC1)C
isomeric SMILES: [O-][n+]1cccc(c1)c1ncn(c1)C(=O)N(C1CCCCC1)C
in ch i key: DOWVMJFBDGWVML-UHFFFAOYSA-N
in ch i: InChI=1S/C16H20N4O2/c1-18(14-7-3-2-4-8-14)16(21)19-11-15(17-12-19)13-6-5-9-20(22)10-13/h5-6,9-12,14H,2-4,7-8H2,1H3
comment: BIA 10-2474 was believed to be reversible inhibitor of fatty acid amide hydrolase (FAAH). It was the cause of a disastrous clinical trial in France which left one participant dead and several others with serious neurological adverse events. The compound is claimed in patent WO2010074588 <Reference id=30420/>. The structure of BIA 10-2474 was disclosed in a clinical trial protocol with EudraCT No: 2015-001799-24. Pharmacological inhibition of FAAH was being investigated in the search for novel analgesic drugs <Reference id=30467/><Reference id=30469/><Reference id=30468/>. More information surrounding this compound and its unfortunate clinical trial outcome is available in two blogposts by our curator Christopher Southan (The unfortunate case of BIA-10-2474 and Molecular details related to BIA 10-2474). Subsequent analysis of BIA 10-2474's pharmacology is reported by van Esbroeck et al. (2017) <Reference id=33310/>. This anaylsis suggests that BIA 10-2474's interaction with FAAH is in fact irreversible. Using activity-based protein profiling (ABPP), this same study reveals that BIA 10-2474 (and its metabolite BIA 10-2639) engages numerous human off-targets including FAAH2 and several lipid serine hydrolases, such as ABHD6, ABHD11, LIPE, and PNPLA6, and xenobiotic drug-metabolizing enzymes CES1, CES2, and CES3, with greater inhibition of ABHD6 and CES2 compared to PNPLA6. The authors postulate that BIA 10-2474 may act to dramatically alter brain lipid metabolism and that this action may have contributed to the compound's neurotoxicity. In the same assays, this action was not replicated by the clinically tested FAAH inhibitor <Ligand id=6694/>. Update: August 2018. BIAL have finally published a primary paper describing their internal characterisation of BIA-10-2474 along with the SAR of that series but only with %inhibition rather than IC50 values <Reference id=36157/>.
iupac name: N-cyclohexyl-N-methyl-4-(1-oxidopyridin-1-ium-3-yl)imidazole-1-carboxamide
synonym: compound 8 l [PubMed: 30113139]
synonym: BIA-10-2474
synonym: BIA-102474
synonym: example 362 [WO2010074588]
approved: f
ligand name: BIA 10-2474
type: SyntheticOrganicLigand

(R)-ARN2508
in ch i key: USQOVYLRWBOSQC-OAHLLOKOSA-N
in ch i: InChI=1S/C22H26FNO4/c1-3-4-5-6-12-24-22(27)28-18-9-7-8-17(13-18)19-11-10-16(14-20(19)23)15(2)21(25)26/h7-11,13-15H,3-6,12H2,1-2H3,(H,24,27)(H,25,26)/t15-/m1/s1
comment: (R)-ARN2508 is an experimental inhibitor of fatty acid amide hydrolase (FAAH) <Reference id=30460/>, claimed in patent WO2014023643 <Reference id=30461/>. The compound series developed by Migliore et al. (2015) <Reference id=30460/> is based on a hybrid scaffold combining structural motifs of the FAAH inhibitor <Ligand id=4339/> and the COX inhibitor <Ligand id=4194/>. The (S) enantiomer (<Ligand id=8999/>) inhibits both FAAH and COX enzyme activities, whereas this (R) enantiomer only inhibits FAAH.
iupac name: (2R)-2-(3-fluoro-4-{3-[(hexylcarbamoyl)oxy]phenyl}phenyl)propanoic acid
synonym: compound (-)-10r [PMID: 26774927]
synonym: example 19 [WO2014023643]
approved: f
ligand name: (R)-ARN2508
type: SyntheticOrganicLigand

(S)-ARN2508
in ch i key: USQOVYLRWBOSQC-HNNXBMFYSA-N
in ch i: InChI=1S/C22H26FNO4/c1-3-4-5-6-12-24-22(27)28-18-9-7-8-17(13-18)19-11-10-16(14-20(19)23)15(2)21(25)26/h7-11,13-15H,3-6,12H2,1-2H3,(H,24,27)(H,25,26)/t15-/m0/s1
comment: (S)-ARN2508 is a dual inhibitor of fatty acid amide hydrolase (FAAH) and COX enzyme activities <Reference id=30460/>, claimed in patent WO2014023643 <Reference id=30461/>. The compound series developed by Migliore et al. (2015) <Reference id=30460/> is based on a hybrid scaffold combining structural motifs of the FAAH inhibitor <Ligand id=4339/> and the COX inhibitor <Ligand id=4194/>. From this series, the (S) enantiomer was found to inhibit both enzymes, whereas the (R) enantiomer (<Ligand id=9000/>) only inhibited FAAH.
iupac name: (2S)-2-(3-fluoro-4-{3-[(hexylcarbamoyl)oxy]phenyl}phenyl)propanoic acid
synonym: compound (+)-10r [PMID: 26774927]
synonym: example 20 [WO2014023643]
approved: f
ligand name: (S)-ARN2508
type: SyntheticOrganicLigand

QAV680
in ch i key: YOPFAMROKXHVCQ-UHFFFAOYSA-N
in ch i: InChI=1S/C18H18N2O4S/c1-12-16(10-17(21)22)15-4-3-9-19-18(15)20(12)11-13-5-7-14(8-6-13)25(2,23)24/h3-9H,10-11H2,1-2H3,(H,21,22)
comment: QAV680 is an investigational antagonist of the prostanoid DP2 receptor (CRTh2) with anti-inflammatory action.
iupac name: 2-[2-methyl-1-[(4-methylsulfonylphenyl)methyl]pyrrolo[5,4-b]pyridin-3-yl]acetic acid
xref: CHEMBL2442750
synonym: NVP-QAV680
approved: f
ligand name: QAV680
type: SyntheticOrganicLigand

fevipiprant
in ch i key: GFPPXZDRVCSVNR-UHFFFAOYSA-N
comment: Fevipiprant is an orally available, selective antagonist of the prostanoid DP2 receptor (CRTh2) with anti-inflammatory action <Reference id=30450/>.
iupac name: 2-[2-methyl-1-[[4-methylsulfonyl-2-(trifluoromethyl)phenyl]methyl]pyrrolo[5,4-b]pyridin-3-yl]acetic acid
xref: CHEMBL3137332
synonym: QAW039
synonym: NVP-QAW039
approved: f
ligand name: fevipiprant
type: SyntheticOrganicLigand

pyridostigmine
canonical SMILES: C[n+]1cccc(c1)OC(=O)N(C)C
isomeric SMILES: C[n+]1cccc(c1)OC(=O)N(C)C
in ch i key: RVOLLAQWKVFTGE-UHFFFAOYSA-N
in ch i: InChI=1S/C9H13N2O2/c1-10(2)9(12)13-8-5-4-6-11(3)7-8/h4-7H,1-3H3/q+1
comment: Pyridostigmine is a peripherally acting, orally active reversible acetylcholinesterase (ACHE) inhibitor, with a slightly longer duration of action than <Ligand id=8993/>. Marketed formulations contain pyridostigmine bromide (PubChem CID 7550).
iupac name: (1-methylpyridin-1-ium-3-yl) N,N-dimethylcarbamate
xref: CHEMBL1115
synonym: Mestinon®
synonym: Regonol®
approved: t
ligand name: pyridostigmine
type: SyntheticOrganicLigand

neostigmine
canonical SMILES: O=C(N(C)C)Oc1cccc(c1)[N+](C)(C)C
isomeric SMILES: O=C(N(C)C)Oc1cccc(c1)[N+](C)(C)C
in ch i key: ALWKGYPQUAPLQC-UHFFFAOYSA-N
in ch i: InChI=1S/C12H19N2O2/c1-13(2)12(15)16-11-8-6-7-10(9-11)14(3,4)5/h6-9H,1-5H3/q+1
comment: Neostigmine is a peripherally acting, reversible acetylcholinesterase (ACHE) inhibitor. Marketed formulations contain neostigmine bromide (PubChem CID 8246) or neostigmine methylsulfate (CID 5824).
iupac name: [3-(dimethylcarbamoyloxy)phenyl]-trimethylazanium
xref: CHEMBL278020
synonym: Prostigmin®
approved: t
ligand name: neostigmine
type: SyntheticOrganicLigand

compound 49 [PMID: 24405707]
in ch i key: UUUGXEGGIAPJQE-MYMUVWEJSA-N
in ch i: InChI=1S/C39H57FN6O3S/c1-38(2,3)17-21-46-35(48)32(50-36(46)29-11-9-12-30(40)34(29)43-22-24-44(25-23-43)39(4,5)6)26-33(47)42-18-15-28(16-19-42)45-20-14-27-10-7-8-13-31(27)41-37(45)49/h7-13,27-28,31-32,36H,14-26H2,1-6H3,(H,41,49)/t27?,31?,32-,36+/m0/s1
comment: Compound 49 is a potent experimental CNS-penetrant thiazolidinone-based CGRP receptor antagonist <Reference id=30447/>. This specific (2R,5S) diastereomer is reported to have an improved brain to plasma ratio compared to <Ligand id=702/> and <Ligand id=703/>, likely attributable to its lower molecular weight and reduced polar surface area (PSA).
iupac name: 3-(1-{2-[(2R,5S)-2-[2-(4-tert-butylpiperazin-1-yl)-3-fluorophenyl]-3-(3,3-dimethylbutyl)-4-oxo-1,3-thiazolidin-5-yl]acetyl}piperidin-4-yl)-2,3,4,5,5a,9a-hexahydro-1H-1,3-benzodiazepin-2-one
approved: f
ligand name: compound 49 [PMID: 24405707]
type: SyntheticOrganicLigand

opicapone
canonical SMILES: OC1=CC(=c2o[nH]c(n2)c2c(C)c(Cl)c([n+](c2Cl)[O-])C)C=C(C1=O)[N+](=O)[O-]
isomeric SMILES: OC1=C/C(=c/2/o[nH]c(n2)c2c(C)c(Cl)c([n+](c2Cl)[O-])C)/C=C(C1=O)[N+](=O)[O-]
in ch i key: HVGGGVAREUUJQV-CHHVJCJISA-N
comment: Opicapone is a novel third generation, long-acting catechol-O-methyltransferase (COMT) inhibitor <Reference id=30428/>. This mechanism reduces peripheral degradation of levodopa as used as Parkinson's disease therapy.
iupac name: (4Z)-4-[3-(2,5-dichloro-4,6-dimethyl-1-oxidopyridin-1-ium-3-yl)-2H-1,2,4-oxadiazol-5-ylidene]-2-hydroxy-6-nitrocyclohexa-2,5-dien-1-one
synonym: Ongentys®
synonym: BIA 9-1067
synonym: compound 37d [PMID: 20334432]
synonym: Ontilyv®
approved: t
ligand name: opicapone
type: SyntheticOrganicLigand

adriforant
canonical SMILES: CNC1CCN(C1)c1cc(NCC2CC2)nc(n1)N
isomeric SMILES: CN[C@@H]1CCN(C1)c1cc(NCC2CC2)nc(n1)N
in ch i key: ISBHYKVAFKTATD-SNVBAGLBSA-N
in ch i: InChI=1S/C13H22N6/c1-15-10-4-5-19(8-10)12-6-11(17-13(14)18-12)16-7-9-2-3-9/h6,9-10,15H,2-5,7-8H2,1H3,(H3,14,16,17,18)/t10-/m1/s1
comment: Adriforant (ZPL-3893787) was a clinical stage immunomodulatory compound being developed by Ziarco Pharma (a Novartis subsidiary). Mechanistically it is a selective histamine H4 receptor antagonist. Novartis announced in their second-quarter financial report of 2020, that they were terminating the adriforant development programme.
iupac name: N'-(cyclopropylmethyl)-6-[(3R)-3-methylaminopyrrolidin-1-yl]pyrimidine-2,4-diamine
xref: CHEMBL1915540
synonym: ZPL-3893787
synonym: ZPL389
synonym: ZPL3893787
synonym: ZPL-389
synonym: PF-03893787
synonym: PF 3893787
approved: f
ligand name: adriforant
type: SyntheticOrganicLigand

JNJ-39758979
canonical SMILES: NC1CCN(C1)c1cc(nc(n1)N)C(C)C
isomeric SMILES: N[C@@H]1CCN(C1)c1cc(nc(n1)N)C(C)C
in ch i key: COOGVHJHSCBOQT-MRVPVSSYSA-N
in ch i: InChI=1S/C11H19N5/c1-7(2)9-5-10(15-11(13)14-9)16-4-3-8(12)6-16/h5,7-8H,3-4,6,12H2,1-2H3,(H2,13,14,15)/t8-/m1/s1
comment: JNJ-39758979 is a selective histamine H4 receptor antagonist <Reference id=32049/> with anti-inflammatory potential.
iupac name: 4-[(3R)-3-aminopyrrolidin-1-yl]-6-propan-2-ylpyrimidin-2-amine
xref: CHEMBL3236549
synonym: JNJ 39758979
synonym: JNJ39758979
approved: f
ligand name: JNJ-39758979
type: SyntheticOrganicLigand

ST-1006
in ch i key: ICAQZJCLBRKWBG-UHFFFAOYSA-N
in ch i: InChI=1S/C16H20Cl2N6/c1-23-5-7-24(8-6-23)15-9-14(21-16(19)22-15)20-10-11-12(17)3-2-4-13(11)18/h2-4,9H,5-8,10H2,1H3,(H3,19,20,21,22)
iupac name: 4-N-[(2,6-dichlorophenyl)methyl]-6-(4-methylpiperazin-1-yl)pyrimidine-2,4-diamine
approved: f
ligand name: ST-1006
type: SyntheticOrganicLigand

INCB-38579
in ch i key: JZAGLPUCLXBELH-UHFFFAOYSA-N
in ch i: InChI=1S/C26H38N6O/c1-30-12-14-31(15-13-30)24-17-23(28-26(27)29-24)21-8-7-20-10-11-32(18-22(20)16-21)25(33)9-6-19-4-2-3-5-19/h7-8,16-17,19,26,29H,2-6,9-15,18,27H2,1H3
iupac name: 1-{7-[2-amino-6-(4-methylpiperazin-1-yl)-1,2-dihydropyrimidin-4-yl]-1,2,3,4-tetrahydroisoquinolin-2-yl}-3-cyclopentylpropan-1-one
approved: f
ligand name: INCB-38579
type: SyntheticOrganicLigand

conessine
in ch i key: GPLGAQQQNWMVMM-MYAJQUOBSA-N
in ch i: InChI=1S/C24H40N2/c1-16-20-8-9-22-19-7-6-17-14-18(25(3)4)10-12-23(17,2)21(19)11-13-24(20,22)15-26(16)5/h6,16,18-22H,7-15H2,1-5H3/t16-,18-,19+,20+,21-,22-,23-,24-/m0/s1
comment: Conessine is an alkaloid obtained from the bark and seeds of Holarrhena antidysenterica trees. It binds with high affinity to rat and human histamine H3 receptors in radio-ligand binding assays, acting as a receptor antagonist <Reference id=31874/><Reference id=31875/>. H3 antagonists are being researched as potential drugs for the treatment of neurodegenerative conditions and for their stimulant and nootropic effects. For example, <Ligand id=8924/> is in clinical trial for Parkinson's disease, narcolepsy, cataplexy and excessive daytime sleepiness.
approved: f
ligand name: conessine
type: NaturalProductLigand

RN-1
in ch i key: YAMSXCOVJUUMCT-FCHUYYIVSA-N
in ch i: InChI=1S/C23H29N3O2/c1-25-11-13-26(14-12-25)23(27)16-24-22-15-21(22)19-7-9-20(10-8-19)28-17-18-5-3-2-4-6-18/h2-10,21-22,24H,11-17H2,1H3/t21-,22+/m0/s1
comment: RN-1 is a brain-penetrant, selective inhibitor of lysine (K)-specific demethylase 1A (KDM1A, LSD1) <Reference id=30419/>. It does not inhibit the structurally related enzymes monoamine oxidase A and B. RN-1 can be used as a tool compound to investigate the role of reversible histone methylation in the function of the nervous system. The dihydrochloride salt (PubChem CID 90488995) is used experimentally.
iupac name: 2-{[(1R,2S)-2-[4-(benzyloxy)phenyl]cyclopropyl]amino}-1-(4-methylpiperazin-1-yl)ethan-1-one
approved: f
ligand name: RN-1
type: SyntheticOrganicLigand

GSK-J4
in ch i key: WBKCKEHGXNWYMO-UHFFFAOYSA-N
in ch i: InChI=1S/C24H27N5O2/c1-2-31-23(30)10-14-26-21-17-22(28-24(27-21)20-9-5-6-13-25-20)29-15-11-18-7-3-4-8-19(18)12-16-29/h3-9,13,17H,2,10-12,14-16H2,1H3,(H,26,27,28)
comment: GSK-J4 is a cell permeable inhibitor of the histone lysine demethylase KDM6 enzymes, lysine (K)-specific demethylase 6A and 6B (common abbrevations UTX and JMJD3 respectively) <Reference id=30418/>. It is the ethyl ester prodrug of <Ligand id=7027/>. GSK-J4 blocks demethylation of histone H3K27.
iupac name: ethyl 3-{[2-(pyridin-2-yl)-6-(2,3,4,5-tetrahydro-1H-3-benzazepin-3-yl)pyrimidin-4-yl]amino}propanoate
xref: CHEMBL3183531
synonym: GSKJ4
synonym: GSK J4
approved: f
ligand name: GSK-J4
type: SyntheticOrganicLigand

quinostatin
in ch i key: TZUJFIBUVNERIP-UHFFFAOYSA-N
in ch i: InChI=1S/C26H27N3O4/c1-2-16-3-5-17(6-4-16)25(30)20-15-28-21-14-23-22(32-11-12-33-23)13-19(21)24(20)29-9-7-18(8-10-29)26(27)31/h3-6,13-15,18H,2,7-12H2,1H3,(H2,27,31)
comment: Quinostatin is an experimental tool compound which inhibits the lipid-kinase activity of the catalytic subunits of class Ia PI3Ks <Reference id=30417/>.
iupac name: 1-[8-(4-ethylbenzoyl)-2,3-dihydro-[1,4]dioxino[2,3-g]quinolin-9-yl]piperidine-4-carboxamide
approved: f
ligand name: quinostatin
type: SyntheticOrganicLigand

HTH-01-015
in ch i key: CHSDJDLAKKAWCI-UHFFFAOYSA-N
in ch i: InChI=1S/C26H28N8O/c1-16-23-24(31-26(29-16)30-19-14-28-34(15-19)20-8-10-27-11-9-20)32(2)22-13-18-7-5-4-6-17(18)12-21(22)25(35)33(23)3/h4-7,12-15,20,27H,8-11H2,1-3H3,(H,29,30,31)
comment: HTH-01-015 is a selective inhibitor of the protein kinase, NUAK family SNF1-like kinase 1 (NUAK1) <Reference id=26615/>. N.B. compare to <Ligand id=8047/> which inhibits both NUAK1 and NUAK2. HTH-01-015 and WZ4003 can be used as chemical probes to delineate the biological roles of the NUAK kinases.
synonym: HTH01-015
approved: f
ligand name: HTH-01-015
type: SyntheticOrganicLigand

omipalisib
in ch i key: CGBJSGAELGCMKE-UHFFFAOYSA-N
comment: Omipalisib (GSK2126458) is a potent dual inhibitor of phosphoinositide 3-kinase α (PI3Kα) and the mammalian target of rapamycin (mTOR). It is compound 1 in <Reference id=30404/>. It was originally developed for anti-proliferative activity in cancer, but has been repositioned as a potential idiopathic pulmonary fibrosis (IPF) therapy <Reference id=34407/>.
iupac name: 2,4-difluoro-N-[2-methoxy-5-(4-pyridazin-4-ylquinolin-6-yl)pyridin-3-yl]benzenesulfonamide
xref: CHEMBL1236962
synonym: GSK-2126458
synonym: GSK 2126458
synonym: GSK2126458
approved: f
ligand name: omipalisib
type: SyntheticOrganicLigand

human GIP(5-30)NH2
in ch i key: NEJABMGLOVSGDX-RKHUIQFASA-N
comment: A synthetic truncated variant of gastric inhibitory polypeptide (GIP) which acts as a high affinity competitive GIP receptor antagonist <Reference id=30398/>.
approved: f
ligand name: human GIP(5-30)NH2
type: PeptideLigand

human GIP(3-30)NH2
in ch i key: IOBVONZFFZDDEF-OTCKMHAFSA-N
comment: A naturally occurring truncated variant of gastric inhibitory polypeptide (GIP) which acts as a high affinity competitive GIP receptor antagonist <Reference id=30398/>.
approved: f
ligand name: human GIP(3-30)NH2
type: PeptideLigand

serabelisib
in ch i key: BLGWHBSBBJNKJO-UHFFFAOYSA-N
in ch i: InChI=1S/C19H17N5O3/c20-19-22-14-9-12(1-3-16(14)27-19)13-2-4-17-21-10-15(24(17)11-13)18(25)23-5-7-26-8-6-23/h1-4,9-11H,5-8H2,(H2,20,22)
comment: Serabelisib (INK-1117) is a potent and selective orally available phosphatidylinositol-3-kinase (PI3K) inhibitor, being investigated for its potential antineoplastic activity. This is compound 54 in patent US20130035324 <Reference id=30396/>.
iupac name: [6-(2-amino-1,3-benzoxazol-5-yl)imidazo[1,2-a]pyridin-3-yl]-morpholin-4-ylmethanone
synonym: MLN1117
synonym: MLN 1117
synonym: INK 1117
synonym: INK1117
synonym: INK-1117
approved: f
ligand name: serabelisib
type: SyntheticOrganicLigand

PIK-108
in ch i key: VRCXIJAYLCUSHC-INIZCTEOSA-N
in ch i: InChI=1S/C22H24N2O3/c1-15-12-18(16(2)23-17-6-4-3-5-7-17)22-19(13-15)20(25)14-21(27-22)24-8-10-26-11-9-24/h3-7,12-14,16,23H,8-11H2,1-2H3/t16-/m0/s1
comment: PIK-108 is an experimental allosteric inhibitor of the lipid modifying kinases, phosphatidylinositol-4,5-bisphosphate 3-kinase catalytic subunits β and δ (PI3Kβ/δ) <Reference id=19774/>. The compound binds at an allosteric site close to the mutation hotspot of H1047R in the mouse PI3Kα C-lobe, in addition to binding at the ATP-binding pocket <Reference id=30394/>.
iupac name: 8-[(1S)-1-anilinoethyl]-6-methyl-2-morpholin-4-ylchromen-4-one
approved: f
ligand name: PIK-108
type: SyntheticOrganicLigand

BO1
canonical SMILES: Fc1ccc(cc1)CSc1nnc(s1)NC(=O)c1ccc(cc1)F
isomeric SMILES: Fc1ccc(cc1)CSc1nnc(s1)NC(=O)c1ccc(cc1)F
in ch i key: ZDYQINDXPNAOKX-UHFFFAOYSA-N
comment: BO1 is a non-ATP competitive, negative allosteric modulator of mutant BCR-ABL kinase proteins <Reference id=30377/>, for example the fusion protein carrying the ABLT315I gatekeeper mutation which confers resistance to <Ligand id=5687/>. Interation of BO1 with the wild type protein shows an ATP-competitive/mixed mechanism of action <Reference id=30377/>.
iupac name: 4-fluoro-N-[5-[(4-fluorophenyl)methylsulfanyl]-1,3,4-thiadiazol-2-yl]benzamide
xref: CHEMBL255738
synonym: Bcr-abl Inhibitor II
approved: f
ligand name: BO1
type: SyntheticOrganicLigand

(5E)-1-(4-fluorophenyl)-5-[(5-methylthiophen-2-yl)methylidene]-2-sulfanylidene-1,3-diazinane-4,6-dione
isomeric SMILES: Fc1ccc(cc1)N1C(=S)NC(=O)/C(=C/c2ccc(s2)C)/C1=O
in ch i key: KXFOCXRVKPGLHA-MDWZMJQESA-N
comment: This compound is a small molecule, reversible inhibitor of the regulator of G-protein signaling 4 (RGS4) protein.
iupac name: (5E)-1-(4-fluorophenyl)-5-[(5-methylthiophen-2-yl)methylidene]-2-sulfanylidene-1,3-diazinane-4,6-dione
xref: CHEMBL1412784
approved: f
ligand name: (5E)-1-(4-fluorophenyl)-5-[(5-methylthiophen-2-yl)methylidene]-2-sulfanylidene-1,3-diazinane-4,6-dione
type: SyntheticOrganicLigand

asciminib
in ch i key: VOVZXURTCKPRDQ-CQSZACIVSA-N
comment: Asciminib (ABL001) is a negative allosteric modulator of BCR-ABL1 <Reference id=30376/><Reference id=36392/><Reference id=36393/><Reference id=41436/>, that induces the kinase to adopt an autoinhibitory, and thereby inactive, conformation <Reference id=36395/>. The compound is the result of a structure-guided medicinal chemistry program targeting the vestigial myristoyl pocket of the ABL1 kinase. The acronym STAMP inhibitor is used to descrobe this class of compound, which specifically targets the ABL myristoyl pocket. The structure of ABL001 was disclosed at the American Society of Hematology's (ASH) 57th Annual Meeting and Exposition in Orlando, Florida (Dec., 2015)- see Abstract 1565. Mechanisms by which resistance to asciminib can develop are reported by Qiang et al. (2017) <Reference id=36394/>, including the development of T315I (confers resistance to <Ligand id=5890/>)-inclusive compound mutations. Combining ponatinib + asciminib has been shown to be effective against such compound mutations <Reference id=43145/>. Asciminib-based PROTACs have been reported <Reference id=41437/>.
iupac name: N-[4-[chloro(difluoro)methoxy]phenyl]-6-[(3R)-3-hydroxypyrrolidin-1-yl]-5-(1H-pyrazol-5-yl)pyridine-3-carboxamide
synonym: Example 9
synonym: ABL001
synonym: ABL-001
synonym: Scemblix®
synonym: compound 1 [PMID: 30137981]
approved: t
ligand name: asciminib
type: SyntheticOrganicLigand

GSK864
in ch i key: DUCNNEYLFOQFSW-PMERELPUSA-N
in ch i: InChI=1S/C30H31FN6O4/c1-17-12-21(13-18(2)25(17)41-4)34-27(38)24-22-15-36(28(39)23-6-5-11-33-23)16-30(3,29(32)40)26(22)37(35-24)14-19-7-9-20(31)10-8-19/h5-13,33H,14-16H2,1-4H3,(H2,32,40)(H,34,38)/t30-/m0/s1
comment: GSK864 is a potent and selective allosteric inhibitor of mutant isocitrate dehydrogenase 1 (IDH1) <Reference id=30372/>. The compound is available from the Structural Genomics Consortium, from their Epigenetics Probes Collection.
iupac name: (7S)-1-[(4-fluorophenyl)methyl]-3-N-(4-methoxy-3,5-dimethylphenyl)-7-methyl-5-(1H-pyrrole-2-carbonyl)-4,6-dihydropyrazolo[4,3-c]pyridine-3,7-dicarboxamide
synonym: compound 4 [PMID: 26436839]
approved: f
ligand name: GSK864
type: SyntheticOrganicLigand

enasidenib
in ch i key: DYLUUSLLRIQKOE-UHFFFAOYSA-N
in ch i: InChI=1S/C19H17F6N7O/c1-17(2,33)9-27-15-30-14(11-4-3-5-12(29-11)18(20,21)22)31-16(32-15)28-10-6-7-26-13(8-10)19(23,24)25/h3-8,33H,9H2,1-2H3,(H2,26,27,28,30,31,32)
comment: Enasidenib (AG-221) is an orally available inhibitor of isocitrate dehygrogenase 2 (IDH2), that is approved as an antineoplastic agent. This compound is example 409 in patent US20130190287 A1 <Reference id=30371/>.
iupac name: 2-methyl-1-[[4-[6-(trifluoromethyl)pyridin-2-yl]-6-[[2-(trifluoromethyl)pyridin-4-yl]amino]-1,3,5-triazin-2-yl]amino]propan-2-ol
synonym: Idhifa®
synonym: AG-221
synonym: CC-90007
approved: t
ligand name: enasidenib
type: SyntheticOrganicLigand

ensartinib
in ch i key: ONPGOSVDVDPBCY-CQSZACIVSA-N
comment: X-396 is an orally available, investigational inhibitor of anaplastic lymphoma receptor tyrosine kinase (ALK). Lovly et al. (2011) report preclinical proof-of-concept findings for the utility of X-396 in ALK-driven cancers <Reference id=30364/>
iupac name: 6-amino-5-[(1R)-1-(2,6-dichloro-3-fluorophenyl)ethoxy]-N-[4-(4-methylpiperazine-1-carbonyl)phenyl]pyridazine-3-carboxamide
synonym: X-396
synonym: Example 18 [WO2012048259]
approved: f
ligand name: ensartinib
type: SyntheticOrganicLigand

enoxacin
in ch i key: IDYZIJYBMGIQMJ-UHFFFAOYSA-N
in ch i: InChI=1S/C15H17FN4O3/c1-2-19-8-10(15(22)23)12(21)9-7-11(16)14(18-13(9)19)20-5-3-17-4-6-20/h7-8,17H,2-6H2,1H3,(H,22,23)
comment: Enoxacin was developed as a oral broad-spectrum fluoroquinolone antibacterial for the treatment of urinary tract infections and gonorrhea. Enoxacin has been reported as an inhibitor of the interaction between the B2 subunit of vacuolar H+-ATPase (ATP6V1B2) and microfilaments <Reference id=30022/>, an interaction required for translocation of the ATPase to the plasma membrane. This process effects activation of osteoclasts and regulates bone resorption, making this interaction a novel target for pharmaceutical intervention to reduce the pathologies associated with bone-loss condtions <Reference id=30023/>.
iupac name: 1-ethyl-6-fluoro-4-oxo-7-piperazin-1-yl-1,8-naphthyridine-3-carboxylic acid
xref: CHEMBL826
synonym: CI-919
synonym: AT-2266
synonym: Penetrex®
approved: t
ligand name: enoxacin
type: SyntheticOrganicLigand

lifirafenib
in ch i key: NGFFVZQXSRKHBM-FKBYEOEOSA-N
in ch i: InChI=1S/C25H17F3N4O3/c26-25(27,28)11-1-4-15-16(9-11)31-24(30-15)21-20-14-10-12(2-5-17(14)35-22(20)21)34-18-7-8-29-23-13(18)3-6-19(33)32-23/h1-2,4-5,7-10,20-22H,3,6H2,(H,30,31)(H,29,32,33)/t20-,21-,22-/m0/s1
comment: Lifirafenib (BGB-283) is an investigational inhibitor of the Raf kinases (ARAF, BRAF, CRAF) and the epidermal growth factor receptor (EGFR) tyrosine kinase <Reference id=30361/>. BGB-283 is being investigated for its antineoplastic activity. The compound is one of the structures described in patent WO2013097224 A1 <Reference id=30363/>.
iupac name: 5-[[(1R,1aS,6bR)-1-[6-(trifluoromethyl)-1H-benzimidazol-2-yl]-1a,6b-dihydro-1H-cyclopropa[b][1]benzofuran-5-yl]oxy]-3,4-dihydro-1H-1,8-naphthyridin-2-one
synonym: BGB-283
synonym: compound 2.2b
approved: f
ligand name: lifirafenib
type: SyntheticOrganicLigand

cerdulatinib
in ch i key: BGLPECHZZQDNCD-UHFFFAOYSA-N
in ch i: InChI=1S/C20H27N7O3S/c1-2-31(29,30)27-11-9-26(10-12-27)16-7-5-15(6-8-16)24-20-22-13-17(18(21)28)19(25-20)23-14-3-4-14/h5-8,13-14H,2-4,9-12H2,1H3,(H2,21,28)(H2,22,23,24,25)
comment: Cerdulatinib (PRT062070) is an investigational kinase inhibitor, with dual activity against Janus kinases (JAKs) and spleen tyrosine kinase (SYK) pathways <Reference id=30360/>.
iupac name: 4-(cyclopropylamino)-2-[4-(4-ethylsulfonylpiperazin-1-yl)anilino]pyrimidine-5-carboxamide
synonym: PRT062070
synonym: PRT-062070
synonym: PRT-2070
synonym: PRT 062070
approved: f
ligand name: cerdulatinib
type: SyntheticOrganicLigand

BAY-678
in ch i key: SHVLFOSIUCIFDN-MUMRKEEXSA-N
in ch i: InChI=1S/C21H16F3N3O2/c1-11-17(12(2)28)19(14-6-7-16(9-25)26-10-14)27-20(29)18(11)13-4-3-5-15(8-13)21(22,23)24/h3-8,10,18-19H,1-2H3,(H,27,29)/t18?,19-/m1/s1
comment: BAY-678 is a selective inhibitor of human neutrophil elastase <Reference id=30356/><Reference id=30357/>. Developed by Bayer, the compound is being made available from the Structural Genomics Consortium's (SGC) Epigenetics Probes Collection.
iupac name: 5-[(2R)-3-acetyl-4-methyl-6-oxo-5-[3-(trifluoromethyl)phenyl]-1,2,5,6-tetrahydropyridin-2-yl]pyridine-2-carbonitrile
approved: f
ligand name: BAY-678
type: SyntheticOrganicLigand

MS023
canonical SMILES: NCCN(Cc1c[nH]cc1c1ccc(cc1)OC(C)C)C
isomeric SMILES: NCCN(Cc1c[nH]cc1c1ccc(cc1)OC(C)C)C
in ch i key: FMTVWAGUJRUAKE-UHFFFAOYSA-N
in ch i: InChI=1S/C17H25N3O/c1-13(2)21-16-6-4-14(5-7-16)17-11-19-10-15(17)12-20(3)9-8-18/h4-7,10-11,13,19H,8-9,12,18H2,1-3H3
comment: MS023 is an inhibitor of type I arginine methyltransferases (PRMTs) <Reference id=30354/><Reference id=30355/>. Type I PRMTs include PRMT1, 3, 4, 6 and 8. These enzymes catalyze mono- and asymmetric dimethylation of arginine residues. MS023 is being made available from the Structural Genomics Consortium's (SGC) Epigenetics Probes Collection.
iupac name: (2-aminoethyl)(methyl)({4-[4-(propan-2-yloxy)phenyl]-1H-pyrrol-3-yl}methyl)amine
approved: f
ligand name: MS023
type: SyntheticOrganicLigand

P6949
canonical SMILES: OC(=O)CCc1cccc(c1)[Sb](=O)(O)O
isomeric SMILES: OC(=O)CCc1cccc(c1)[Sb](=O)(O)O
in ch i key: VXMRXQJADBGVFN-UHFFFAOYSA-L
in ch i: InChI=1S/C9H9O2.2H2O.O.Sb/c10-9(11)7-6-8-4-2-1-3-5-8;;;;/h1-2,4-5H,6-7H2,(H,10,11);2*1H2;;/q;;;;+2/p-2
comment: P6949 is a arylstibonate compound designed to inhibit Cdc25a (CDC25A; P30304) and Cdc25b (CDC25B; P30305) phosphatase activity <Reference id=30017/>. It also inhibits protein tyrosine phosphatase PTP-β (PTPRB, P23467) by ≥90%.
iupac name: 3-(3-stibonophenyl)propanoic acid
xref: CHEMBL2057662
approved: f
ligand name: P6949
type: SyntheticOrganicLigand

GSK591
in ch i key: TWKYXZSXXXKKJU-FQEVSTJZSA-N
in ch i: InChI=1S/C22H28N4O2/c27-20(15-26-11-9-16-4-1-2-5-18(16)14-26)13-24-22(28)17-8-10-23-21(12-17)25-19-6-3-7-19/h1-2,4-5,8,10,12,19-20,27H,3,6-7,9,11,13-15H2,(H,23,25)(H,24,28)/t20-/m0/s1
comment: GSK591 is a potent inhibitor of the arginine methyltransferase PRMT5 <Reference id=30352/><Reference id=30353/>. This in vivo tool compound is a result of collaboration between Epizyme and GlaxoSmithKline, and is being made available as part of the Structural Genomics Consortium's Epigenetics Probes Collection.
iupac name: 2-(cyclobutylamino)-N-[(2S)-2-hydroxy-3-(1,2,3,4-tetrahydroisoquinolin-2-yl)propyl]pyridine-4-carboxamide
synonym: EPZ015866
synonym: GSK3203591
approved: f
ligand name: GSK591
type: SyntheticOrganicLigand

BAY-598
in ch i key: OTTJIRVZJJGFTK-SFHVURJKSA-N
comment: BAY-598 is an inhibitor of the lysine methyltransferase SMYD2 <Reference id=30349/>. Developed in a collaboration between Bayer and the Structural Genomics Consortium, the compound is available from the SGC's epigenetic probes set.
iupac name: N-[(4S)-1-[(Z)-N'-cyano-N-[3-(difluoromethoxy)phenyl]carbamimidoyl]-3-(3,4-dichlorophenyl)-4,5-dihydro-1H-pyrazol-4-yl]-N-ethyl-2-hydroxyacetamide
approved: f
ligand name: BAY-598
type: SyntheticOrganicLigand

fimepinostat
in ch i key: JOWXJLIFIIOYMS-UHFFFAOYSA-N
in ch i: InChI=1S/C23H24N8O4S/c1-30(23-25-11-15(12-26-23)22(32)29-33)13-16-9-17-19(36-16)21(31-5-7-35-8-6-31)28-20(27-17)14-3-4-18(34-2)24-10-14/h3-4,9-12,33H,5-8,13H2,1-2H3,(H,29,32)
comment: Fimepinostat (CUDC-907) is an investigational dual inhibitor of histone deacetylase (HDAC) and phosphatidylinositol 3-kinase (PI3K) activity <Reference id=30348/>. The compound is orally available.
iupac name: N-hydroxy-2-[[2-(6-methoxypyridin-3-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl-methylamino]pyrimidine-5-carboxamide
synonym: CUDC-907
synonym: CUDC 907
synonym: PI3K/HDAC Inhibitor centn
approved: f
ligand name: fimepinostat
type: SyntheticOrganicLigand

NVS-1
in ch i key: XVECNLUKQDKOST-UHFFFAOYSA-N
in ch i: InChI=1S/C27H37N5O2S/c1-6-13-35(33,34)25-29-22(15-24(30-25)28-20-8-9-20)18-7-10-23-19(14-18)11-12-32(23)21-16-26(2,3)31-27(4,5)17-21/h7,10-12,14-15,20-21,31H,6,8-9,13,16-17H2,1-5H3,(H,28,29,30)
comment: NVS-1 is a small-molecule selective inhibitor of the bromodomain-containing protein cat eye syndrome chromosome region, candidate 2 (CECR2) <Reference id=30347/>. NVS-1 is one of the compounds available from the Structural Genomics Consortium's epigenetic probes set. It was developed in collaboration with Novartis.
iupac name: N-cyclopropyl-2-(propane-1-sulfonyl)-6-[1-(2,2,6,6-tetramethylpiperidin-4-yl)-1H-indol-5-yl]pyrimidin-4-amine
synonym: NVS-CECR2-1
approved: f
ligand name: NVS-1
type: SyntheticOrganicLigand

BI-9564
in ch i key: BJFSUDWKXGMUKA-UHFFFAOYSA-N
in ch i: InChI=1S/C20H23N3O3/c1-22(2)11-13-8-19(26-5)15(9-18(13)25-4)17-12-23(3)20(24)16-10-21-7-6-14(16)17/h6-10,12H,11H2,1-5H3
comment: BI-9564 is an inhibitor of bromodomains in BRD7 and BRD9 <Reference id=30917/><Reference id=30932/>. BI-9564 is one of the compounds available from the Structural Genomics Consortium's epigenetic probes set. It was developed in collaboration with Boehringer Ingelheim.
iupac name: 4-{4-[(dimethylamino)methyl]-2,5-dimethoxyphenyl}-2-methyl-1,2-dihydro-2,7-naphthyridin-1-one
approved: f
ligand name: BI-9564
type: SyntheticOrganicLigand

AZD5069
in ch i key: QZECRCLSIGFCIO-RISCZKNCSA-N
comment: AZD5069 is a novel, selective antagonist of the chemokine receptor, CXCR2. The structure shown here was drawn from that in <Reference id=30333/>, which specifies stereochemistry. This structure is identical to Example 47 in patent US7838675 <Reference id=30334/>. PubChem records the structure with no specified stereochemistry (CID 59558839). Small-molecule antagonists of CXCR2 are being developed for their potential to treat inflammatory conditions.
iupac name: N-[2-[(2,3-difluorophenyl)methylsulfanyl]-6-[(2R,3S)-3,4-dihydroxybutan-2-yl]oxypyrimidin-4-yl]azetidine-1-sulfonamide
synonym: AZD-5069
approved: f
ligand name: AZD5069
type: SyntheticOrganicLigand

JNJ-46281222
in ch i key: LYDKDODJIBQNLK-UHFFFAOYSA-N
in ch i: InChI=1S/C23H25F3N4/c24-23(25,26)21-19(10-13-30-20(14-16-6-7-16)27-28-22(21)30)15-29-11-8-18(9-12-29)17-4-2-1-3-5-17/h1-5,10,13,16,18H,6-9,11-12,14-15H2
comment: JNJ-40411813 is a selective and potent positive allosteric modulator (PAM) of the metabotropic glutamate receptor 2 (mGlu2) <Reference id=30331/>. PAM binding shows a preference for a G protein bound state of the receptor.
iupac name: 3-(cyclopropylmethyl)-7-[(4-phenylpiperidin-1-yl)methyl]-8-(trifluoromethyl)-[1,2,4]triazolo[4,3-a]pyridine
approved: f
ligand name: JNJ-46281222
type: SyntheticOrganicLigand

JNJ-40411813
canonical SMILES: CCCCn1ccc(c(c1=O)Cl)N1CCC(CC1)c1ccccc1
isomeric SMILES: CCCCn1ccc(c(c1=O)Cl)N1CCC(CC1)c1ccccc1
in ch i key: HYOGJHCDLQSAHX-UHFFFAOYSA-N
in ch i: InChI=1S/C20H25ClN2O/c1-2-3-12-23-15-11-18(19(21)20(23)24)22-13-9-17(10-14-22)16-7-5-4-6-8-16/h4-8,11,15,17H,2-3,9-10,12-14H2,1H3
comment: JNJ-40411813 is a positive allosteric modulator (PAM) of the metabotropic glutamate receptor 2 (mGlu2) <Reference id=30330/><Reference id=36730/>.
iupac name: 1-butyl-3-chloro-4-(4-phenyl-1-piperidinyl)-2(1H)-pyridinone
synonym: ADX-71149
synonym: JNJ40411813
synonym: JNJ 40411813
synonym: ADX71149
approved: f
ligand name: JNJ-40411813
type: SyntheticOrganicLigand

CCT251545
in ch i key: LBFYQISQYCGDDW-UHFFFAOYSA-N
in ch i: InChI=1S/C23H24ClN5O/c1-28-15-18(12-27-28)16-2-4-17(5-3-16)19-13-25-14-20(24)21(19)29-10-7-23(8-11-29)6-9-26-22(23)30/h2-5,12-15H,6-11H2,1H3,(H,26,30)
comment: CCT251545 is a small molecule inhibitor of WNT signalling <Reference id=30328/>. The molecular targets of CCT251545 are the protein kinases CDK8 and CDK19 <Reference id=30329/>. This is a type I inhibitor, binding in a DMG-in mode.
iupac name: 8-[3-chloro-5-[4-(1-methylpyrazol-4-yl)phenyl]pyridin-4-yl]-2,8-diazaspiro[4.5]decan-1-one
approved: f
ligand name: CCT251545
type: SyntheticOrganicLigand

LY3009120
in ch i key: HHCBMISMPSAZBF-UHFFFAOYSA-N
in ch i: InChI=1S/C23H29FN6O/c1-13-9-18(24)19(29-22(31)26-8-7-23(3,4)5)11-16(13)17-10-15-12-27-21(25-6)30-20(15)28-14(17)2/h9-12H,7-8H2,1-6H3,(H2,26,29,31)(H,25,27,28,30)
comment: LY3009120 is a pan-RAF kinase and RAF dimer inhibitor <Reference id=30325/>.
iupac name: 1-(3,3-dimethylbutyl)-3-[2-fluoro-4-methyl-5-[7-methyl-2-(methylamino)pyrido[2,3-d]pyrimidin-6-yl]phenyl]urea
synonym: LY-3009120
approved: f
ligand name: LY3009120
type: SyntheticOrganicLigand

edicotinib
in ch i key: BNVPFDRNGHMRJS-UHFFFAOYSA-N
in ch i: InChI=1S/C27H35N5O2/c1-25(2)11-9-17(10-12-25)22-21(32-24(33)23-29-16-19(15-28)30-23)8-7-20(31-22)18-13-26(3,4)34-27(5,6)14-18/h7-9,16,18H,10-14H2,1-6H3,(H,29,30)(H,32,33)
comment: Edicotinib (PRV-6527; previously JNJ-40346527) was identified in a medicinal-chemistry lead optimization study to develop oral, selective CSF1R kinase inhibitors. The chemical structure is compound I-S in patent US20140045789 <Reference id=30323/>. PubChem CID 25230468 is a tautomer which is also claimed in the patent.
iupac name: 4-cyano-N-[2-(4,4-dimethylcyclohex-1-en-1-yl)-6-(2,2,6,6-tetramethyloxan-4-yl)pyridin-3-yl]-1H-imidazole-2-carboxamide
synonym: JNJ-40346527
synonym: JNJ40346527
synonym: US8497376, 15
approved: f
ligand name: edicotinib
type: SyntheticOrganicLigand

compound 4 [PMID: 24432870]
canonical SMILES: OCC(C#Cc1ccc2c(c1)n(c1ncnc(n1)N)c(n2)C)(O)C
isomeric SMILES: OCC(C#Cc1ccc2c(c1)n(c1ncnc(n1)N)c(n2)C)(O)C
in ch i key: XFZMSTKVAOPBGR-UHFFFAOYSA-N
in ch i: InChI=1S/C16H16N6O2/c1-10-20-12-4-3-11(5-6-16(2,24)8-23)7-13(12)22(10)15-19-9-18-14(17)21-15/h3-4,7,9,23-24H,8H2,1-2H3,(H2,17,18,19,21)
comment: Compound 4 [PMID: 24432870] is an inhibitor of group 2 p21 protein (Cdc42/Rac)-activated kinases (PAK4, PAK6 and PAK7) <Reference id=30315/>.
iupac name: 4-[3-(4-amino-1,3,5-triazin-2-yl)-2-methylbenzimidazol-5-yl]-2-methylbut-3-yne-1,2-diol
xref: CHEMBL3128046
approved: f
ligand name: compound 4 [PMID: 24432870]
type: SyntheticOrganicLigand

IPA-3
canonical SMILES: Oc1ccc2c(c1SSc1c(O)ccc3c1cccc3)cccc2
isomeric SMILES: Oc1ccc2c(c1SSc1c(O)ccc3c1cccc3)cccc2
in ch i key: RFAXLXKIAKIUDT-UHFFFAOYSA-N
in ch i: InChI=1S/C20H14O2S2/c21-17-11-9-13-5-1-3-7-15(13)19(17)23-24-20-16-8-4-2-6-14(16)10-12-18(20)22/h1-12,21-22H
comment: IPA-3 is a cell-permeable, non-ATP-competitive (allosteric), selective inhibitor of p21 protein (Cdc42/Rac)-activated kinase 1 (PAK1) <Reference id=30319/>. IPA-3 binds covalently to the autoregulatory domain of PAK1, preventing its activation by Cdc42 <Reference id=30320/>. Its redox activity makes it a poor experimental tool.
iupac name: 1-(2-hydroxynaphthalen-1-yl)disulfanylnaphthalen-2-ol
xref: CHEMBL472940
synonym: IPA3
approved: f
ligand name: IPA-3
type: SyntheticOrganicLigand

FRAX597
in ch i key: DHUJCQOUWQMVCG-UHFFFAOYSA-N
in ch i: InChI=1S/C29H28ClN7OS/c1-3-37-27-20(14-24(28(37)38)23-9-4-19(15-25(23)30)26-17-31-18-39-26)16-32-29(34-27)33-21-5-7-22(8-6-21)36-12-10-35(2)11-13-36/h4-9,14-18H,3,10-13H2,1-2H3,(H,32,33,34)
comment: FRAX597 is an inhibitor of group 1 p21 protein (Cdc42/Rac)-activated kinases (PAK1, PAK2 and PAK3) <Reference id=30318/>, exhibiting experimental anti-cancer action.
iupac name: 6-[2-chloro-4-(1,3-thiazol-5-yl)phenyl]-8-ethyl-2-[4-(4-methylpiperazin-1-yl)anilino]pyrido[2,3-d]pyrimidin-7-one
approved: f
ligand name: FRAX597
type: SyntheticOrganicLigand

PP1
canonical SMILES: Cc1ccc(cc1)c1nn(c2c1c(N)ncn2)C(C)(C)C
isomeric SMILES: Cc1ccc(cc1)c1nn(c2c1c(N)ncn2)C(C)(C)C
in ch i key: ZVPDNRVYHLRXLX-UHFFFAOYSA-N
in ch i: InChI=1S/C16H19N5/c1-10-5-7-11(8-6-10)13-12-14(17)18-9-19-15(12)21(20-13)16(2,3)4/h5-9H,1-4H3,(H2,17,18,19)
comment: PP1 is a multi-kinase inhibitor.
iupac name: 1-tert-butyl-3-(4-methylphenyl)pyrazolo[4,5-e]pyrimidin-4-amine
xref: CHEMBL306380
synonym: pyrazolopyrimidine 1
approved: f
ligand name: PP1
type: SyntheticOrganicLigand

FRAX486
in ch i key: DHKFOIHIUYFSOF-UHFFFAOYSA-N
comment: FRAX486 is a brain penetrant and orally bioavailable inhibitor of group 1 p21 protein (Cdc42/Rac)-activated kinases (PAK1, PAK2 and PAK3; PAKA subfamily) <Reference id=30317/>. Experimental evidence suggests inhibition of PAKs may offer neuroprotective <Reference id=30326/><Reference id=30317/> and anti-cancer potential.
iupac name: 6-(2,4-dichlorophenyl)-8-ethyl-2-(3-fluoro-4-piperazin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one
approved: f
ligand name: FRAX486
type: SyntheticOrganicLigand

PF-3758309
in ch i key: AYCPARAPKDAOEN-LJQANCHMSA-N
in ch i: InChI=1S/C25H30N8OS/c1-15-26-18-11-12-35-20(18)23(27-15)29-22-17-13-33(25(2,3)21(17)30-31-22)24(34)28-19(14-32(4)5)16-9-7-6-8-10-16/h6-12,19H,13-14H2,1-5H3,(H,28,34)(H2,26,27,29,30,31)/t19-/m1/s1
comment: PF-3758309 is an inhibitor of the p21 protein (Cdc42/Rac)-activated kinase (PAK) kinases <Reference id=30315/><Reference id=30313/>.
iupac name: N-[(1S)-2-(dimethylamino)-1-phenylethyl]-6,6-dimethyl-3-[(2-methylthieno[3,2-d]pyrimidin-4-yl)amino]-1,4-dihydropyrrolo[3,4-c]pyrazole-5-carboxamide
xref: CHEMBL3128043
synonym: PF-03758309
synonym: PF3758309
synonym: example 114 [US8530652]
synonym: compound 1 [PMID: 24432870]
approved: f
ligand name: PF-3758309
type: SyntheticOrganicLigand

compound 3 [PMID: 26191365]
in ch i key: QPXRZHIUNWUCFG-UHFFFAOYSA-N
comment: Compound 3 [PMID: 26191365] is a highly selective, negative allosteric regulator of the protein kinase, p21 protein (Cdc42/Rac)-activated kinase 1 (PAK1) with favourable physicochemical properties <Reference id=30312/>. Structurally the compound resembles the benzodiazepine core and was optimised from lead compounds discovered in a fragment-based screen to identify novel structural motifs inhibiting kinase activity. It binds to a site adjacent to the kinase's ATP binding site <Reference id=30312/>.
approved: f
ligand name: compound 3 [PMID: 26191365]
type: SyntheticOrganicLigand

pitolisant
canonical SMILES: Clc1ccc(cc1)CCCOCCCN1CCCCC1
isomeric SMILES: Clc1ccc(cc1)CCCOCCCN1CCCCC1
in ch i key: NNACHAUCXXVJSP-UHFFFAOYSA-N
in ch i: InChI=1S/C17H26ClNO/c18-17-9-7-16(8-10-17)6-4-14-20-15-5-13-19-11-2-1-3-12-19/h7-10H,1-6,11-15H2
comment: Pitolisant is a selective antagonist/inverse agonist of the histamine H3 receptor <Reference id=30246/><Reference id=30247/><Reference id=22851/>.
iupac name: 1-[3-[3-(4-chlorophenyl)propoxy]propyl]piperidine
xref: CHEMBL462605
synonym: tiprolisant [USAN]
synonym: BF2.649
synonym: Wakix®
synonym: Ozawade®
approved: t
ligand name: pitolisant
type: SyntheticOrganicLigand

AR-67
in ch i key: XUSKJHCMMWAAHV-SANMLTNESA-N
in ch i: InChI=1S/C26H30N2O5Si/c1-7-26(32)18-11-20-21-16(12-28(20)23(30)17(18)13-33-24(26)31)22(34(5,6)25(2,3)4)15-10-14(29)8-9-19(15)27-21/h8-11,29,32H,7,12-13H2,1-6H3/t26-/m0/s1
comment: AR-67 is a synthetic, highly lipophilic derivative of the natural alkaloid camptothecin (PubChem CID 24360), with potential antineoplastic <Reference id=30165/><Reference id=30168/> and radiosensitizing activities <Reference id=30164/>. The compound has improved physicochemical properties compared to other camptothecin-derived drugs (e.g. <Ligand id=6925/>, the active metabolite of the anti-cancer drug <Ligand id=6823/>, and <Ligand id=7101/>) <Reference id=30166/>.
xref: CHEMBL412309
synonym: AR67
synonym: DB-67
synonym: DB67
synonym: DB 67
synonym: AR 67
synonym: silatecan
synonym: compound 14 [PMID:11052802]
approved: f
ligand name: AR-67
type: SyntheticOrganicLigand

samotolisib
in ch i key: ACCFLVVUVBJNGT-AWEZNQCLSA-N
in ch i: InChI=1S/C23H26N4O3/c1-14(30-5)13-27-21-18-9-15(16-8-17(11-24-10-16)23(2,3)29)6-7-19(18)25-12-20(21)26(4)22(27)28/h6-12,14,29H,13H2,1-5H3/t14-/m0/s1
comment: samotolisib (LY3023414) is a dual inhibitor of phosphoinositide 3-kinase α (PI3Kα) and the serine/threonine kinase mTOR ( mechanistic target of rapamycin) <Reference id=30160/>, with potential antineoplastic activity.
iupac name: 8-[5-(2-hydroxypropan-2-yl)pyridin-3-yl]-1-[(2S)-2-methoxypropyl]-3-methylimidazo[4,5-c]quinolin-2-one
synonym: LY-3023414
synonym: example 1 [US8440829]
synonym: LY3023414
approved: f
ligand name: samotolisib
type: SyntheticOrganicLigand

AMG319
in ch i key: KWRYMZHCQIOOEB-LBPRGKRZSA-N
in ch i: InChI=1S/C21H16FN7/c1-12(28-21-19-20(25-10-24-19)26-11-27-21)15-8-13-5-6-14(22)9-17(13)29-18(15)16-4-2-3-7-23-16/h2-12H,1H3,(H2,24,25,26,27,28)/t12-/m0/s1
comment: AMG319 is an inhibitor of phosphoinositide 3-kinase δ (PI3Kδ) inhibitor, with potential clinical anti-inflammatory utility <Reference id=30159/>.
iupac name: N-[(1S)-1-(7-fluoro-2-pyridin-2-ylquinolin-3-yl)ethyl]-7H-purin-6-amine
synonym: AMG-319
synonym: AMG 319
approved: f
ligand name: AMG319
type: SyntheticOrganicLigand

umbralisib
in ch i key: IUVCFHHAEHNCFT-INIZCTEOSA-N
in ch i: InChI=1S/C31H24F3N5O3/c1-15(2)41-24-9-7-18(12-22(24)34)27-26-30(35)36-14-37-31(26)39(38-27)16(3)29-25(17-5-4-6-19(32)11-17)28(40)21-13-20(33)8-10-23(21)42-29/h4-16H,1-3H3,(H2,35,36,37)/t16-/m0/s1
comment: Umbralisib (TGR-1202; RP5264,) is an orally available, selective inhibitor of the δ isoform of phosphoinositide 3-kinase (PI3K) <Reference id=36785/><Reference id=30158/><Reference id=37471/>, that was developed by TG Therapeutics for the treatment of several B cell malignancies. It also inhibits casein kinase-1ε <Reference id=34569/>. For clinical application umbralisib is formulated as the tosylate salt.
iupac name: 2-[(1S)-1-[4-amino-3-(3-fluoro-4-propan-2-yloxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-6-fluoro-3-(3-fluorophenyl)chromen-4-one
xref: CHEMBL3948730
synonym: RP5264
synonym: TGR-1202
synonym: TGR1202
synonym: RP-5264
synonym: example A1 [US2014011819]
synonym: Ukoniq®
approved: t
ligand name: umbralisib
type: SyntheticOrganicLigand

AZD8835
in ch i key: ZGRDYKFVDCFJCZ-UHFFFAOYSA-N
in ch i: InChI=1S/C22H31N9O3/c1-5-31-19(26-18(29-31)13-6-9-30(10-7-13)15(33)8-11-32)14-12-24-17(23)16(25-14)20-27-28-21(34-20)22(2,3)4/h12-13,32H,5-11H2,1-4H3,(H2,23,24)
comment: AZD8835 is an inhibitor of the α and δ isoforms of phosphoinositide 3-kinase (PI3K) <Reference id=30157/>. The compound's physical properties suggest it is suitable for oral administration.
iupac name: 1-(4-{5-[5-amino-6-(5-tert-butyl-1,3,4-oxadiazol-2-yl)pyrazin-2-yl]-1-ethyl-1H-1,2,4-triazol-3-yl}piperidin-1-yl)-3-hydroxypropan-1-one
synonym: AZD 8835
synonym: compound 25 [PMID: 26475521]
synonym: AZD-8835
approved: f
ligand name: AZD8835
type: SyntheticOrganicLigand

onatasertib
in ch i key: UFKLYTOEMRFKAD-UHFFFAOYSA-N
in ch i: InChI=1S/C21H27N5O3/c1-21(2,28)17-9-4-13(10-22-17)16-11-23-19-20(25-16)26(18(27)12-24-19)14-5-7-15(29-3)8-6-14/h4,9-11,14-15,28H,5-8,12H2,1-3H3,(H,23,24)
comment: Onatasertib (CC-223) is an investigational inhibitor of the serine/threonine kinase, mechanistic target of rapamycin (mTOR) in mTORC1/2 complexes <Reference id=30150/><Reference id=30151/>.
iupac name: 3-[6-(2-hydroxypropan-2-yl)pyridin-3-yl]-5-(4-methoxycyclohexyl)-7,8-dihydropyrazino[2,3-b]pyrazin-6-one
synonym: compound 37 [PMID: 26083478]
synonym: CC-223
synonym: CC223
approved: f
ligand name: onatasertib
type: SyntheticOrganicLigand

AMG-337
in ch i key: DWHXUGDWKAIASB-CQSZACIVSA-N
in ch i: InChI=1S/C23H22FN7O3/c1-14(30-5-4-20-18(23(30)32)9-17(11-25-20)34-7-6-33-3)21-27-28-22-19(24)8-15(13-31(21)22)16-10-26-29(2)12-16/h4-5,8-14H,6-7H2,1-3H3/t14-/m1/s1
comment: AMG337 is an investigational inhibitor of the MET proto-oncogene receptor tyrosine kinase (a.k.a. hepatocyte growth factor receptor or c-MET). It has been designed to decrease its inhibitory effect on CYP3A4 metabolic activity (i.e. its liability of inhibiting hepatic drug metabolism) <Reference id=30148/><Reference id=30149/>. AMG337 is the R-enantiomer and it adopts a U-shaped binding mode in the kinase ATP binding pocket. The S-enantiomer is unable to interact in the same pocket.
iupac name: 6-[(1R)-1-[8-fluoro-6-(1-methylpyrazol-4-yl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl]ethyl]-3-(2-methoxyethoxy)-1,6-naphthyridin-5-one
xref: CHEMBL3785909
synonym: AMG 337
synonym: AMG-337
synonym: compound 24 [PMID: 19819693]
approved: f
ligand name: AMG-337
type: SyntheticOrganicLigand

acalabrutinib
in ch i key: WDENQIQQYWYTPO-IBGZPJMESA-N
in ch i: InChI=1S/C26H23N7O2/c1-2-6-21(34)32-15-5-7-19(32)25-31-22(23-24(27)29-14-16-33(23)25)17-9-11-18(12-10-17)26(35)30-20-8-3-4-13-28-20/h3-4,8-14,16,19H,5,7,15H2,1H3,(H2,27,29)(H,28,30,35)/t19-/m0/s1
comment: Acalabrutinib is an orally available second-generation, selective and irreversible inhibitor of Bruton tyrosine kinase (BTK) <Reference id=33436/>, being investigated for its potential antineoplastic activity (in multiple haematologic malignancies and solid tumours), as well as a potential therapy for rheumatoid arthritis. Acalabrutinib covalently bonds to Cysteine-481 in BTK.
iupac name: 4-[8-amino-3-[(2S)-1-but-2-ynoylpyrrolidin-2-yl]imidazo[1,5-a]pyrazin-1-yl]-N-pyridin-2-ylbenzamide
synonym: Calquence®
synonym: ACP-196
synonym: Example 6 [US20140155385 A1]
approved: t
ligand name: acalabrutinib
type: SyntheticOrganicLigand

verosudil
in ch i key: VDYRZXYYQMMFJW-UHFFFAOYSA-N
in ch i: InChI=1S/C17H17N3O2S/c1-20(2)15(12-6-8-23-10-12)17(22)19-13-3-4-14-11(9-13)5-7-18-16(14)21/h3-10,15H,1-2H3,(H,18,21)(H,19,22)
comment: Verosudil is an investigational Rho kinase inhibitor. The INN record for verosudil indicates that this is a racemic mixture. We show the chemical structure without stereochemistry to represent the mixture. The (2S)-isomer is represented in PubChem CID 86270580 and the (2R)-isomer is represented in CID 44198631.
iupac name: 2-(dimethylamino)-N-(1-oxo-2H-isoquinolin-6-yl)-2-thiophen-3-ylacetamide
synonym: AR-12286
synonym: AR 12286
approved: f
ligand name: verosudil
type: SyntheticOrganicLigand

SAR407899
canonical SMILES: O=c1[nH]ccc2c1ccc(c2)OC1CCNCC1
isomeric SMILES: O=c1[nH]ccc2c1ccc(c2)OC1CCNCC1
in ch i key: IPEXHQGMTHOKQV-UHFFFAOYSA-N
in ch i: InChI=1S/C14H16N2O2/c17-14-13-2-1-12(9-10(13)3-8-16-14)18-11-4-6-15-7-5-11/h1-3,8-9,11,15H,4-7H2,(H,16,17)
comment: SAR407899 is a potent ATP-competitive, Rho kinase inhibitor <Reference id=30145/>.
iupac name: 6-piperidin-4-yloxy-2H-isoquinolin-1-one
xref: CHEMBL1667969
synonym: HY-15687A
synonym: SAR-407899
approved: f
ligand name: SAR407899
type: SyntheticOrganicLigand

larotrectinib
in ch i key: NYNZQNWKBKUAII-KBXCAEBGSA-N
in ch i: InChI=1S/C21H22F2N6O2/c22-13-3-4-16(23)15(10-13)18-2-1-7-28(18)19-6-9-29-20(26-19)17(11-24-29)25-21(31)27-8-5-14(30)12-27/h3-4,6,9-11,14,18,30H,1-2,5,7-8,12H2,(H,25,31)/t14-,18+/m0/s1
comment: Larotrectinib (LOXO-101) is an orally available, potent and selective inhibitor of the receptor tyrosine kinases of the TRK family <Reference id=30140/><Reference id=30139/>. In these referenced patents, data is provided for inhibition of neurotrophic tyrosine kinase, receptor, type 1 (NTRK1, a.k.a. TrkA) .
iupac name: (3S)-N-[5-[(2R)-2-(2,5-difluorophenyl)pyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-3-yl]-3-hydroxypyrrolidine-1-carboxamide
synonym: Vitrakvi®
synonym: example 14 [US8865698 B2]
synonym: (S)-N-(5-((R)-2-(2,5-difluorophenyl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-hydroxypyrrolidine-1-carboxamide
synonym: LOXO-101
approved: t
ligand name: larotrectinib
type: SyntheticOrganicLigand

GSK5182
isomeric SMILES: OCCC/C(=C(/c1ccc(cc1)O)/c1ccc(cc1)OCCN(C)C)/c1ccccc1
in ch i key: ZVSFNBNLNLXEFQ-RQZHXJHFSA-N
in ch i: InChI=1S/C27H31NO3/c1-28(2)18-20-31-25-16-12-23(13-17-25)27(22-10-14-24(30)15-11-22)26(9-6-19-29)21-7-4-3-5-8-21/h3-5,7-8,10-17,29-30H,6,9,18-20H2,1-2H3/b27-26-
comment: GSK5182 is an analogue of <Ligand id=1016/>. It binds the ligand binding domain of the estrogen related receptor γ (ERRγ), acting as an inverse agonist <Reference id=30110/>.
iupac name: 4-[(Z)-1-[4-(2-dimethylaminoethoxy)phenyl]-5-hydroxy-2-phenylpent-1-enyl]phenol
xref: CHEMBL201013
synonym: GSK 5182
synonym: GSK-5182
approved: f
ligand name: GSK5182
type: SyntheticOrganicLigand

edaglitazone
in ch i key: HAAXAFNSRADSMK-UHFFFAOYSA-N
in ch i: InChI=1S/C24H20N2O4S2/c1-14-18(25-23(30-14)15-5-3-2-4-6-15)9-11-29-19-8-7-16(21-17(19)10-12-31-21)13-20-22(27)26-24(28)32-20/h2-8,10,12,20H,9,11,13H2,1H3,(H,26,27,28)
comment: Edaglitazone is a potent and selective peroxisome proliferator-activated (PPARγ) receptor agonist <Reference id=30108/><Reference id=30109/>. The INN record for edaglitazone confirms a racemic mixture of stereoisomers. We show the structure without defined stereochemistry to represent the mixture.
iupac name: 5-[[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]-1-benzothiophen-7-yl]methyl]-1,3-thiazolidine-2,4-dione
synonym: BM 131258
synonym: R 483
synonym: BM13.1258
approved: f
ligand name: edaglitazone
type: SyntheticOrganicLigand

CD2314
in ch i key: URUSABQSUCBGGJ-UHFFFAOYSA-N
in ch i: InChI=1S/C23H24O2S/c1-22(2)7-8-23(3,4)19-11-16-9-15(6-5-14(16)10-18(19)22)20-12-17(13-26-20)21(24)25/h5-6,9-13H,7-8H2,1-4H3,(H,24,25)
comment: CD2314 is a potent and selective retinoic acid receptor β (RARβ) agonist <Reference id=30106/><Reference id=30107/>.
iupac name: 5-(5,5,8,8-tetramethyl-6,7-dihydroanthracen-2-yl)thiophene-3-carboxylic acid
synonym: CD-2314
synonym: CD 2314
approved: f
ligand name: CD2314
type: SyntheticOrganicLigand

PA452
in ch i key: JJUUTJCZMGZJDZ-UHFFFAOYSA-N
in ch i: InChI=1S/C26H37N3O3/c1-7-8-9-10-13-32-22-15-20-19(25(2,3)11-12-26(20,4)5)14-21(22)29(6)24-27-16-18(17-28-24)23(30)31/h14-17H,7-13H2,1-6H3,(H,30,31)
comment: PA452 is a retinoid X receptor (RXR) antagonist <Reference id=30099/><Reference id=10814/>. The compound causes the dissociation of RXR tetramers.
iupac name: 2-[(3-hexoxy-5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)-methylamino]pyrimidine-5-carboxylic acid
xref: CHEMBL115097
synonym: PA 452
synonym: PA-452
synonym: compound 9 [PMID: 24900278]
synonym: compound 6b [PMID: 12139443]
approved: f
ligand name: PA452
type: SyntheticOrganicLigand

fluorobexarotene
in ch i key: LWKAWHRSPCHMPJ-UHFFFAOYSA-N
in ch i: InChI=1S/C24H27FO2/c1-14-11-19-20(24(5,6)10-9-23(19,3)4)13-18(14)15(2)16-7-8-17(22(26)27)21(25)12-16/h7-8,11-13H,2,9-10H2,1,3-6H3,(H,26,27)
comment: Fluorobexarotene is a retinoid X receptor agonist <Reference id=30098/>.
iupac name: 2-fluoro-4-[1-(3,5,5,8,8-pentamethyl-6,7-dihydronaphthalen-2-yl)ethenyl]benzoic acid
approved: f
ligand name: fluorobexarotene
type: SyntheticOrganicLigand

zinc protoporphyrin IX
canonical SMILES: C=CC1=C(C)C2=NC1=Cc1[n-]c(c(c1C)CCC(=O)O)C=C1N=C(C=c3[n-]c(=C2)c(C=C)c3C)C(=C1CCC(=O)O)C.[Zn+2]
isomeric SMILES: C=CC1=C(C)C2=NC1=Cc1[n-]c(c(c1C)CCC(=O)O)C=C1N=C(C=c3[n-]c(=C2)c(C=C)c3C)C(=C1CCC(=O)O)C.[Zn+2]
in ch i key: FUTVBRXUIKZACV-UHFFFAOYSA-L
in ch i: InChI=1S/C34H34N4O4.Zn/c1-7-21-17(3)25-13-26-19(5)23(9-11-33(39)40)31(37-26)16-32-24(10-12-34(41)42)20(6)28(38-32)15-30-22(8-2)18(4)27(36-30)14-29(21)35-25;/h7-8,13-16H,1-2,9-12H2,3-6H3,(H4,35,36,37,38,39,40,41,42);/q;+2/p-2
comment: ZnPP is reported as an antagonist of the estrogen receptor β <Reference id=30097/>. The PubChem identifier for protoporphyrin IX is CID 4971. This is a very similar structure to iron bound heme, but with the ferrous ion replaced by a zinc ion.
synonym: protoporphyrin IX containing Zn
approved: f
ligand name: zinc protoporphyrin IX
type: SyntheticOrganicLigand

cobalt protoporphyrin IX
canonical SMILES: C=CC1=C(C)C2=NC1=Cc1[n-]c(c(c1C)CCC(=O)O)C=C1N=C(C=c3[n-]c(=C2)c(C=C)c3C)C(=C1CCC(=O)O)C.[Co+2]
isomeric SMILES: C=CC1=C(C)C2=NC1=Cc1[n-]c(c(c1C)CCC(=O)O)C=C1N=C(C=c3[n-]c(=C2)c(C=C)c3C)C(=C1CCC(=O)O)C.[Co+2]
in ch i key: AQTFKGDWFRRIHR-UHFFFAOYSA-L
in ch i: InChI=1S/C34H34N4O4.Co/c1-7-21-17(3)25-13-26-19(5)23(9-11-33(39)40)31(37-26)16-32-24(10-12-34(41)42)20(6)28(38-32)15-30-22(8-2)18(4)27(36-30)14-29(21)35-25;/h7-8,13-16H,1-2,9-12H2,3-6H3,(H4,35,36,37,38,39,40,41,42);/q;+2/p-2
comment: CoPP is reported as an antagonist of the estrogen receptor β <Reference id=30097/>. The PubChem identifier for protoporphyrin IX is CID 4971. This is a very similar structure to iron-bound <Ligand id=4349/>, but with the ferrous ion replaced by a cobalt ion.
synonym: protoporphyrin IX containing Co
approved: f
ligand name: cobalt protoporphyrin IX
type: SyntheticOrganicLigand

SR9009
canonical SMILES: CCOC(=O)N1CCC(C1)CN(Cc1ccc(s1)[N+](=O)[O-])Cc1ccc(cc1)Cl
isomeric SMILES: CCOC(=O)N1CCC(C1)CN(Cc1ccc(s1)[N+](=O)[O-])Cc1ccc(cc1)Cl
in ch i key: MMJJNHOIVCGAAP-UHFFFAOYSA-N
comment: SR9009 is an estrogen receptor β agonist <Reference id=30096/>.
iupac name: ethyl 3-[[(4-chlorophenyl)methyl-[(5-nitrothiophen-2-yl)methyl]amino]methyl]pyrrolidine-1-carboxylate
xref: CHEMBL1961796
approved: f
ligand name: SR9009
type: SyntheticOrganicLigand

SR9011
canonical SMILES: CCCCCNC(=O)N1CCC(C1)CN(Cc1ccc(s1)[N+](=O)[O-])Cc1ccc(cc1)Cl
isomeric SMILES: CCCCCNC(=O)N1CCC(C1)CN(Cc1ccc(s1)[N+](=O)[O-])Cc1ccc(cc1)Cl
in ch i key: PPUYOYQTTWJTIU-UHFFFAOYSA-N
comment: SR9011 is an estrogen receptor β agonist <Reference id=30096/>.
iupac name: 3-[[(4-chlorophenyl)methyl-[(5-nitrothiophen-2-yl)methyl]amino]methyl]-N-pentylpyrrolidine-1-carboxamide
xref: CHEMBL1961797
approved: f
ligand name: SR9011
type: SyntheticOrganicLigand

liquiritigenin
canonical SMILES: Oc1ccc(cc1)C1CC(=O)c2c(O1)cc(cc2)O
isomeric SMILES: Oc1ccc(cc1)C1CC(=O)c2c(O1)cc(cc2)O
in ch i key: FURUXTVZLHCCNA-UHFFFAOYSA-N
in ch i: InChI=1S/C15H12O4/c16-10-3-1-9(2-4-10)14-8-13(18)12-6-5-11(17)7-15(12)19-14/h1-7,14,16-17H,8H2
comment: Liquiritigenin is a selective estrogen receptor β agonist isolated from the root of Glycyrrhizae uralensis Fisch (a type of Chinese liquorice) <Reference id=30095/>. We show the structure without specified stereochemistry. The compound exhibits anti-inflammatory actions <Reference id=30095/>.
iupac name: 7-hydroxy-2-(4-hydroxyphenyl)chroman-4-one
xref: CHEMBL271939
approved: f
ligand name: liquiritigenin
type: NaturalProductLigand

FERb 033
canonical SMILES: ON=Cc1ccc(c(c1O)Cl)c1ccc(c(c1)F)O
isomeric SMILES: O/N=C/c1ccc(c(c1O)Cl)c1ccc(c(c1)F)O
in ch i key: LRRMQNGSYOUANY-OMCISZLKSA-N
in ch i: InChI=1S/C13H9ClFNO3/c14-12-9(3-1-8(6-16-19)13(12)18)7-2-4-11(17)10(15)5-7/h1-6,17-19H/b16-6+
comment: FERb 033 is a potent and selective estrogen receptor β agonist <Reference id=30094/>. PubChem CID 74429219 represents this molecule with slightly different structure.
iupac name: 2-chloro-3-(3-fluoro-4-hydroxyphenyl)-6-[(1E)-(hydroxyimino)methyl]phenol
synonym: compound 3 [PMID: 19128016]
approved: f
ligand name: FERb 033
type: SyntheticOrganicLigand

AC-186
canonical SMILES: Oc1ccc(cc1)C1(CCC(CC1)(F)F)c1ccccc1F
isomeric SMILES: Oc1ccc(cc1)C1(CCC(CC1)(F)F)c1ccccc1F
in ch i key: HSMUKSLNDJOZQG-UHFFFAOYSA-N
in ch i: InChI=1S/C18H17F3O/c19-16-4-2-1-3-15(16)17(9-11-18(20,21)12-10-17)13-5-7-14(22)8-6-13/h1-8,22H,9-12H2
comment: AC-186 is reported as a selective nonsteroidal estrogen receptor agonist <Reference id=30092/>.
iupac name: 4-[4,4-difluoro-1-(2-fluorophenyl)cyclohexyl]phenol
synonym: AC 186
approved: f
ligand name: AC-186
type: SyntheticOrganicLigand

KMUP-1
in ch i key: NIDVDYQCGWISJZ-UHFFFAOYSA-N
in ch i: InChI=1S/C19H23ClN6O2/c1-22-17-16(18(27)23(2)19(22)28)26(13-21-17)12-9-24-7-10-25(11-8-24)15-6-4-3-5-14(15)20/h3-6,13H,7-12H2,1-2H3
comment: KMUP-1 is a novel xanthine-based activator of soluble guanylyl cyclase (sGC) (acts to enhance cGMP levels) reported to be useful clinically for tracheal relaxation <Reference id=30084/>. It also has anti-inflammatory actions. Studies in aninals suggest this compound may also be a candidate for clinical investigation as a treatment for pulmonary arterial hypertension <Reference id=30087/> or erectile dysfunction <Reference id=30086/>.
iupac name: 7-[2-[4-(2-chlorophenyl)piperazin-1-yl]ethyl]-1,3-dimethylpurine-2,6-dione
synonym: KMUP 1
approved: f
ligand name: KMUP-1
type: SyntheticOrganicLigand

VPC171
in ch i key: HNHLVOBHWXLIGP-UHFFFAOYSA-N
in ch i: InChI=1S/C18H12F3NOS/c19-18(20,21)13-8-4-7-12(9-13)14-10-24-17(22)15(14)16(23)11-5-2-1-3-6-11/h1-10H,22H2
comment: VPC171 is a positive allosteric modulator (PAM) of the adenosine A1 receptor (A1R). It is compound 9a in Aurelio et al. (2009) <Reference id=30082/>. PAMs of the A1R are being investigated as a novel treatment approach for neuropathic pain <Reference id=30083/>.
iupac name: [2-amino-4-[3-(trifluoromethyl)phenyl]thiophen-3-yl]-phenylmethanone
xref: CHEMBL404477
approved: f
ligand name: VPC171
type: SyntheticOrganicLigand

CUDC-101
in ch i key: PLIVFNIUGLLCEK-UHFFFAOYSA-N
in ch i: InChI=1S/C24H26N4O4/c1-3-17-9-8-10-18(13-17)27-24-19-14-22(21(31-2)15-20(19)25-16-26-24)32-12-7-5-4-6-11-23(29)28-30/h1,8-10,13-16,30H,4-7,11-12H2,2H3,(H,28,29)(H,25,26,27)
comment: CUDC-101 is an orally available Phase I compound which is multiacting, inhibiting class I/II histone deacetylases (HDACs) but not the class III sirtuins, and the type I receptor tyrosine kinases EGFR and ERBB2 (HER2) <Reference id=30079/>. Targeting two pathogenic pathways simultaneously is one of the strategies being evaluated to overcome problems associated with molecular heterogeneity of tumours and the development of drug resistance.
iupac name: 7-[4-(3-ethynylanilino)-7-methoxyquinazolin-6-yl]oxy-N-hydroxyheptanamide
xref: CHEMBL598797
synonym: CUDC 101
synonym: CUDC101
synonym: compound 8 [PMID: 20143778]
approved: f
ligand name: CUDC-101
type: SyntheticOrganicLigand

compound 5z [PMID: 8410981]
in ch i key: RPFYDENHBPRCTN-NRFANRHFSA-N
in ch i: InChI=1S/C21H16N2O6/c1-2-21(26)13-5-15-18-11(7-23(15)19(24)12(13)8-27-20(21)25)3-10-4-16-17(29-9-28-16)6-14(10)22-18/h3-6,26H,2,7-9H2,1H3/t21-/m0/s1
comment: Compound 5z is an analogue of the natural alkaloid camptothecin (PubChem CID 24360) <Reference id=30076/>.
xref: CHEMBL307794
synonym: 10,11-Methylenedioxy-20S-camptothecin
approved: f
ligand name: compound 5z [PMID: 8410981]
type: SyntheticOrganicLigand

compound 19 [PMID: 7707314]
in ch i key: WBLBIGPXRKCBEI-FQEVSTJZSA-N
in ch i: InChI=1S/C20H16BrN3O4/c1-3-20(27)13-5-15-17-11(7-24(15)18(25)12(13)8-28-19(20)26)9(2)10-4-16(21)22-6-14(10)23-17/h4-6,27H,3,7-8H2,1-2H3/t20-/m0/s1
comment: Compound 19 is reported as an inhibitor of topoisomerase I <Reference id=30075/>.
xref: CHEMBL13935
approved: f
ligand name: compound 19 [PMID: 7707314]
type: SyntheticOrganicLigand

SGI-1027
in ch i key: QSYLKMKIVWJAAK-UHFFFAOYSA-N
in ch i: InChI=1S/C27H23N7O/c1-17-16-25(34-27(28)30-17)32-20-10-12-21(13-11-20)33-26(35)18-6-8-19(9-7-18)31-24-14-15-29-23-5-3-2-4-22(23)24/h2-16H,1H3,(H,29,31)(H,33,35)(H3,28,30,32,34)
comment: SGI-1027 is a non-nucleoside inhibitor of human DNA methyltransferase DNMT1 <Reference id=30074/>. Alternative analogues are also investigated in <Reference id=30074/>.
iupac name: N-[4-[(2-amino-6-methylpyrimidin-4-yl)amino]phenyl]-4-(quinolin-4-ylamino)benzamide
xref: CHEMBL2336409
synonym: SGI 1027
synonym: SGI1027
approved: f
ligand name: SGI-1027
type: SyntheticOrganicLigand

compound 9 [PMID: 15615544]
in ch i key: NYPQVENKFXVRKJ-ZDUSSCGKSA-N
in ch i: InChI=1S/C20H20N8O5/c21-16-15-17(27-20(22)26-16)24-7-11(25-15)6-23-10-1-2-12-9(5-10)8-28(18(12)31)13(19(32)33)3-4-14(29)30/h1-2,5,7,13,23H,3-4,6,8H2,(H,29,30)(H,32,33)(H4,21,22,24,26,27)/t13-/m0/s1
comment: Compound 9 is an analogue of aminopterin (the 4-amino derivative of folic acid; PubChem CID 2154; related to <Ligand id=4815/>), but with a rotationally restricted side chain amide bond. Compound 9 manifests antifolate activity in vitro, achieved by inhibiting both dihydrofolate reductase (DHFR) and folate transporter 1 (reduced folate carrier) activities <Reference id=30073/>.
iupac name: (2S)-2-[6-[(2,4-diaminopteridin-6-yl)methylamino]-3-oxo-1H-isoindol-2-yl]pentanedioic acid
xref: CHEMBL390990
approved: f
ligand name: compound 9 [PMID: 15615544]
type: SyntheticOrganicLigand

compound 1a [PMID: 18573659]
in ch i key: SXVZDDYARZWATR-KRWDZBQOSA-N
comment: Compound 1a is a rationally designed urotensin-II receptor (UTS2R) antagonist <Reference id=30013/>.
iupac name: N-[(3S)-1-[(3-bromo-4-piperidin-4-yloxyphenyl)methyl]pyrrolidin-3-yl]-3,4-dichlorobenzamide
xref: CHEMBL495075
approved: f
ligand name: compound 1a [PMID: 18573659]
type: SyntheticOrganicLigand

(2S,4S)-ketoconazole
in ch i key: XMAYWYJOQHXEEK-JYFHCDHNSA-N
comment: This is a stereoisomer of <Ligand id=2568/>.
iupac name: 1-[4-[4-[[(2S,4S)-2-(2,4-dichlorophenyl)-2-(imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]piperazin-1-yl]ethanone
xref: CHEMBL319160
approved: f
ligand name: (2S,4S)-ketoconazole
type: SyntheticOrganicLigand

AT-076
in ch i key: LGYDWJJZDCXEOV-JWQCQUIFSA-N
in ch i: InChI=1S/C26H35N3O3/c1-17(2)25(16-29-10-8-18(9-11-29)19-4-3-5-22(30)12-19)28-26(32)24-14-20-6-7-23(31)13-21(20)15-27-24/h3-7,12-13,17-18,24-25,27,30-31H,8-11,14-16H2,1-2H3,(H,28,32)/t24-,25-/m1/s1
comment: AT-076 is an experimental pan antagonist of the opioid receptor family <Reference id=30004/>.
iupac name: (3R)-7-hydroxy-N-[(2S)-1-[4-(3-hydroxyphenyl)piperidin-1-yl]-3-methylbutan-2-yl]-1,2,3,4-tetrahydroisoquinoline-3-carboxamide
approved: f
ligand name: AT-076
type: SyntheticOrganicLigand

compound 13 [PMID: 23098072]
in ch i key: UNILWMWFPHPYOR-KXEYIPSPSA-M
comment: This is a dye-labelled Toll-like receptor 2 agonist, designed for targeted pancreatic cancer imaging <Reference id=30066/>. The unlabelled compound (10; PubChem CID 71451937) has potential immunotherapeutic action.
xref: CHEMBL2179401
approved: f
ligand name: compound 13 [PMID: 23098072]
type: SyntheticOrganicLigand

ML130
canonical SMILES: Cc1ccc(cc1)S(=O)(=O)n1c(N)nc2c1cccc2
isomeric SMILES: Cc1ccc(cc1)S(=O)(=O)n1c(N)nc2c1cccc2
in ch i key: SRFABRWQVPCPRG-UHFFFAOYSA-N
in ch i: InChI=1S/C14H13N3O2S/c1-10-6-8-11(9-7-10)20(18,19)17-13-5-3-2-4-12(13)16-14(17)15/h2-9H,1H3,(H2,15,16)
comment: ML130 is reported as a selective inhibitor of the pattern recognition receptor, NOD1 (nucleotide-binding oligomerization domain containing 1) <Reference id=30062/><Reference id=33589/>.
iupac name: 1-(4-methylphenyl)sulfonylbenzimidazol-2-amine
xref: CHEMBL1412853
synonym: compound 1c [PMID: 22003428]
synonym: Noditinib-1
synonym: ML 130
synonym: ML-130
approved: f
ligand name: ML130
type: SyntheticOrganicLigand

compound 8 [PMID: 17562362}
in ch i key: JQCXJCAKYWSWCH-UHFFFAOYSA-N
comment: Compound 8 is the most potent N-methyl-D-aspartate receptor antagonist reported in <Reference id=30042/>. The compound is likely to bind to the glycine binding site of the GluN1 component of the receptor.
iupac name: 2-[(6-chloro-7-methyl-2,3-dioxo-1,4-dihydroquinoxalin-5-yl)-methylsulfonylamino]acetic acid
xref: CHEMBL248247
approved: f
ligand name: compound 8 [PMID: 17562362}
type: SyntheticOrganicLigand

compound 30 [PMID: 22468970]
isomeric SMILES: O=C1S/C(=C/c2ccc(c(c2)C(F)(F)F)O)/C(=O)N1CC(CC(F)(F)F)(CC(F)(F)F)C
in ch i key: KSFQOHIAWRETBP-XGICHPGQSA-N
in ch i: InChI=1S/C18H14F9NO3S/c1-15(6-16(19,20)21,7-17(22,23)24)8-28-13(30)12(32-14(28)31)5-9-2-3-11(29)10(4-9)18(25,26)27/h2-5,29H,6-8H2,1H3/b12-5-
comment: Compound 30 acts as a negative allosteric modulator of GLUT1-mediated glucose import in to tumour cells (LNCaP cells) and this effects apoptotic cell death <Reference id=30032/>.
iupac name: (5Z)-5-[[4-hydroxy-3-(trifluoromethyl)phenyl]methylidene]-3-[4,4,4-trifluoro-2-methyl-2-(2,2,2-trifluoroethyl)butyl]-1,3-thiazolidine-2,4-dione
xref: CHEMBL2058262
approved: f
ligand name: compound 30 [PMID: 22468970]
type: SyntheticOrganicLigand

compound 21 [PMID: 23981033]
in ch i key: ZXUGLISADYYLBK-UHFFFAOYSA-N
in ch i: InChI=1S/C25H29N5O3/c1-24(2,3)30-15-18-14-25(27-22(31)21(18)28-30)9-11-29(12-10-25)23(32)17-6-5-16-7-8-20(33-4)26-19(16)13-17/h5-8,13,15H,9-12,14H2,1-4H3,(H,27,31)
comment: Compound 21 is reported as aSpirolactam-based lead compound inhibitor of acetyl-CoA carboxylase (ACC), inhibiting both ACC1 and ACC2 <Reference id=30027/>. Although not the most potent inhibitor in the series, compound 21 was progressed to preclinical studies based on its selectivity profile and favourable pharmacokinetic properties.
iupac name: 2-tert-butyl-1'-(2-methoxyquinoline-7-carbonyl)spiro[4,6-dihydropyrazolo[3,4-c]pyridine-5,4'-piperidine]-7-one
xref: CHEMBL2419596
approved: f
ligand name: compound 21 [PMID: 23981033]
type: SyntheticOrganicLigand

PhTX-11
in ch i key: OZVULFLAPUPPFK-QFIPXVFZSA-N
in ch i: InChI=1S/C24H41N3O3/c1-2-12-23(29)27-22(19-20-13-15-21(28)16-14-20)24(30)26-18-11-9-7-5-3-4-6-8-10-17-25/h13-16,22,28H,2-12,17-19,25H2,1H3,(H,26,30)(H,27,29)/t22-/m0/s1
comment: PhTX-11 is reported as a potent noncompetitive antagonist of nicotinic acetylcholine receptors containing the δ subunit <Reference id=30026/>.
iupac name: N-[(2S)-1-(11-aminoundecylamino)-3-(4-hydroxyphenyl)-1-oxopropan-2-yl]butanamide
xref: CHEMBL16044
synonym: compound 7e
approved: f
ligand name: PhTX-11
type: SyntheticOrganicLigand

compound 1a [PMID: 23597791]
in ch i key: UYFZCWXRMHSLTC-UHFFFAOYSA-N
in ch i: InChI=1S/C20H17N5O2S3/c1-2-13-5-7-15(8-6-13)30(26,27)20-19-22-18(21-12-14-4-3-10-28-14)17-16(9-11-29-17)25(19)24-23-20/h3-11H,2,12H2,1H3,(H,21,22)
comment: Compound 1a is reported as a small molecule inhibitor of human urea transport protein, UTB (SLC14A1) and may exemplify compounds with a novel diuretic mechanism of action <Reference id=30021/>.
xref: CHEMBL1394231
approved: f
ligand name: compound 1a [PMID: 23597791]
type: SyntheticOrganicLigand

IU1
canonical SMILES: Fc1ccc(cc1)n1c(C)cc(c1C)C(=O)CN1CCCC1
isomeric SMILES: Fc1ccc(cc1)n1c(C)cc(c1C)C(=O)CN1CCCC1
in ch i key: JUWDSDKJBMFLHE-UHFFFAOYSA-N
in ch i: InChI=1S/C18H21FN2O/c1-13-11-17(18(22)12-20-9-3-4-10-20)14(2)21(13)16-7-5-15(19)6-8-16/h5-8,11H,3-4,9-10,12H2,1-2H3
comment: Compound IU1 is a reversible, small molecule inhibitor, discovered in a high-throughput study to identify inhibitors of the human proteasome-associated deubiquitinating enzyme USP14 <Reference id=30020/>. Based on in vitro and in vivo results, the authors hypothesise that inhibition of USP14 may protect cells from the toxic effects of oxidised proteins produced in cells experiencing oxidative stress and that this may be a useful strategy for limiting the damaging effects of certain proteasome substrates associated with neurodegenerative diseases.
iupac name: 1-[1-(4-fluorophenyl)-2,5-dimethylpyrrol-3-yl]-2-pyrrolidin-1-ylethanone
xref: CHEMBL1410015
approved: f
ligand name: IU1
type: SyntheticOrganicLigand

RBM2-1B
canonical SMILES: CCCCCCCCCCCCCSC=CC(NC(=O)CCCCCCC)CO
isomeric SMILES: CCCCCCCCCCCCCS/C=C/[C@@H](NC(=O)CCCCCCC)CO
in ch i key: NYZFADNSXWSJDZ-PPEFQKSUSA-N
in ch i: InChI=1S/C25H49NO2S/c1-3-5-7-9-10-11-12-13-14-16-18-21-29-22-20-24(23-27)26-25(28)19-17-15-8-6-4-2/h20,22,24,27H,3-19,21,23H2,1-2H3,(H,26,28)/b22-20+/t24-/m1/s1
comment: RBM2-1B is the most potent inhibitor of dihydroceramide desaturase 1 (DES1; official gene name delta(4)-desaturase, sphingolipid 1, DEGS1) reported in <Reference id=30019/>.
iupac name: N-[(E,2R)-1-hydroxy-4-tridecylsulfanylbut-3-en-2-yl]octanamide
xref: CHEMBL2024680
approved: f
ligand name: RBM2-1B
type: SyntheticOrganicLigand

AS1949490
canonical SMILES: Clc1ccc(cc1)COc1ccsc1C(=O)NC(c1ccccc1)C
in ch i key: RFZPGNRLOKVZJY-AWEZNQCLSA-N
in ch i: InChI=1S/C20H18ClNO2S/c1-14(16-5-3-2-4-6-16)22-20(23)19-18(11-12-25-19)24-13-15-7-9-17(21)10-8-15/h2-12,14H,13H2,1H3,(H,22,23)/t14-/m0/s1
comment: AS1949490 is a small molecule inhibitor of SH2 domain-containing inositol 5'-phosphatase 2 (SHIP2, a.k.a. inositol polyphosphate phosphatase-like 1, with gene symbol INPPL1) <Reference id=30018/> which can be used as a tool compound to elucidate the normal and pathophysiological roles of SHIP2.
iupac name: 3-[(4-chlorophenyl)methoxy]-N-[(1S)-1-phenylethyl]thiophene-2-carboxamide
xref: CHEMBL2337806
synonym: AS 1949490
synonym: AS-1949490
approved: f
ligand name: AS1949490
type: SyntheticOrganicLigand

MS363
isomeric SMILES: NC1=C(Cl)C(=O)C(=C/C/1=N/Nc1ccc(cc1)S(=O)(=O)Nc1ccccn1)C
in ch i key: GLWPTCULLHMSCO-OEAKJJBVSA-N
comment: MS363 is one of the lead compounds identified using a structure-guided design approach to discover inhibitors for the BET bromodomains, with highest affinity for the bromodomains of BRD3 and BRD4 <Reference id=24603/>.
iupac name: 4-[(2E)-2-(2-amino-3-chloro-5-methyl-4-oxocyclohexa-2,5-dien-1-ylidene)hydrazinyl]-N-pyridin-2-ylbenzenesulfonamide
xref: CHEMBL3086885
synonym: compound 29
approved: f
ligand name: MS363
type: SyntheticOrganicLigand

compound 39 [PMID: 23623673]
in ch i key: VTGCIWWYBFGGNJ-UHFFFAOYSA-N
in ch i: InChI=1S/C22H13ClFN3O/c23-15-7-4-8-16(24)18(15)21-26-19-14-10-9-13(12-5-2-1-3-6-12)11-17(14)25-22(28)20(19)27-21/h1-11H,(H,25,28)(H,26,27)
comment: Compound 39 is reported as a selective inhibitor of microsomal prostaglandin E2 synthase-1 (mPGES1; PTGES) <Reference id=30016/>. The compound was screened against other prostaglandin/leukotriene synthetic enzymes to assess selectivity.
iupac name: 2-(2-chloro-6-fluorophenyl)-7-phenyl-3,5-dihydroimidazo[4,5-c]quinolin-4-one
xref: CHEMBL2387503
approved: f
ligand name: compound 39 [PMID: 23623673]
type: SyntheticOrganicLigand

compound 33 [PMID: 19908842]
in ch i key: VMJFQUMKCMNFSX-UHFFFAOYSA-N
in ch i: InChI=1S/C14H8F4N6/c15-7-1-8(16)3-9(2-7)21-13-12-14(23-11(4-19)22-13)24(6-20-12)5-10(17)18/h1-3,6,10H,5H2,(H,21,22,23)
comment: Compound 33 was developed in a study to identify anti-parasitic compounds which are inhibitors of Trypanosomal cysteine proteases <Reference id=30015/>. The lead compounds were tetsed against a panel of human proteases to assess selectivity.
iupac name: 6-(3,5-difluoroanilino)-9-(2,2-difluoroethyl)purine-2-carbonitrile
xref: CHEMBL578159
approved: f
ligand name: compound 33 [PMID: 19908842]
type: SyntheticOrganicLigand

compound 1 [PMID: 16821802]
canonical SMILES: CC1COC(O1)(CCc1ccc(cc1)Cl)Cn1cncc1
in ch i key: PUVVRSXPYYFNAP-CZUORRHYSA-N
in ch i: InChI=1S/C16H19ClN2O2/c1-13-10-20-16(21-13,11-19-9-8-18-12-19)7-6-14-2-4-15(17)5-3-14/h2-5,8-9,12-13H,6-7,10-11H2,1H3/t13-,16-/m1/s1
comment: Compound 1 is reported as a novel inhibitor of spleen-derived heme oxygenase (haem oxygenase 1, HMOX1; human and rat) <Reference id=30014/>. The compound may be used experimentally as the hydrochloride salt (PubChem CID 11624320).
iupac name: 1-[[(2R,4R)-2-[2-(4-chlorophenyl)ethyl]-4-methyl-1,3-dioxolan-2-yl]methyl]imidazole
xref: CHEMBL463223
synonym: imidazole-dioxolane 1
approved: f
ligand name: compound 1 [PMID: 16821802]
type: SyntheticOrganicLigand

SCH486757
in ch i key: MQWMHMZNBGQNMT-LDSCYUJKSA-N
in ch i: InChI=1S/C24H23Cl2N3O/c25-20-8-3-1-6-18(20)22(19-7-2-4-9-21(19)26)29-16-10-11-17(29)15-24(30,14-16)23-27-12-5-13-28-23/h1-9,12-13,16-17,22,30H,10-11,14-15H2/t16-,17+,24?
comment: SCH486757 is a preclinical nociceptin/orphanin FQ peptide (NOP) receptor agonist <Reference id=29999/>, with cough suppressing (antitussive) activity.
iupac name: (1R,5S)-8-[bis(2-chlorophenyl)methyl]-3-pyrimidin-2-yl-8-azabicyclo[3.2.1]octan-3-ol
approved: f
ligand name: SCH486757
type: SyntheticOrganicLigand

SCH221510
in ch i key: LOSJNRBXNQTUNT-UHFFFAOYSA-N
in ch i: InChI=1S/C28H31NO/c1-20-10-6-8-14-25(20)27(26-15-9-7-11-21(26)2)29-23-16-17-24(29)19-28(30,18-23)22-12-4-3-5-13-22/h3-15,23-24,27,30H,16-19H2,1-2H3
comment: SCH221510 is a novel piperidine type, orally active nociceptin opioid (NOP) receptor agonist <Reference id=29998/>.
iupac name: 8-[bis(2-methylphenyl)methyl]-3-phenyl-8-azabicyclo[3.2.1]octan-3-ol
xref: CHEMBL513136
synonym: SCH 221510
synonym: SCH-221510
approved: f
ligand name: SCH221510
type: SyntheticOrganicLigand

SR16835
in ch i key: SZKWDIATUVLAAW-UHFFFAOYSA-N
in ch i: InChI=1S/C26H30N2O/c29-25-17-20-5-1-2-10-23(20)28(25)21-13-15-27(16-14-21)24-12-11-19-7-3-6-18-8-4-9-22(24)26(18)19/h1-2,4-5,8-10,19,21,24H,3,6-7,11-17H2
comment: SR16835 is an experimental NOP receptor agonist, with low-affinity bifunctional activity at the μ opioid receptor.
iupac name: 1-[1-(2,3,3a,4,5,6-hexahydro-1H-phenalen-1-yl)piperidin-4-yl]-3H-indol-2-one
xref: CHEMBL3262554
synonym: AT-202
approved: f
ligand name: SR16835
type: SyntheticOrganicLigand

cebranopadol
in ch i key: CSMVOZKEWSOFER-UHFFFAOYSA-N
in ch i: InChI=1S/C24H27FN2O/c1-27(2)23(17-6-4-3-5-7-17)11-13-24(14-12-23)22-19(10-15-28-24)20-16-18(25)8-9-21(20)26-22/h3-9,16,26H,10-15H2,1-2H3
comment: This compound is a novel benzenoid opioid analgesic <Reference id=29994/><Reference id=29995/><Reference id=29996/>, being assessed in clinical trials for various acute and chronic pain conditions. The compound is non-selective, acting at more than one member of the opioid receptor family <Reference id=36594/><Reference id=36595/>.
iupac name: 6-fluoro-N,N-dimethyl-1'-phenylspiro[4,9-dihydro-3H-pyrano[3,4-b]indole-1,4'-cyclohexane]-1'-amine
xref: CHEMBL2364605
synonym: GRT6005
synonym: GRT-6005
synonym: GRT 6005
approved: f
ligand name: cebranopadol
type: SyntheticOrganicLigand

NCRW0005-F05
canonical SMILES: COc1ccc(cc1)C1N(c2ccccc2)C(=O)C1(F)F
isomeric SMILES: COc1ccc(cc1)C1N(c2ccccc2)C(=O)C1(F)F
in ch i key: AIIIYUSGINMZMS-UHFFFAOYSA-N
in ch i: InChI=1S/C16H13F2NO2/c1-21-13-9-7-11(8-10-13)14-16(17,18)15(20)19(14)12-5-3-2-4-6-12/h2-10,14H,1H3
comment: NCRW0005-F05 is the highest affinity antagonist of GPR139 <Reference id=29829/> identified from a high-throughput screening study <Reference id=29829/>.
iupac name: 3,3-difluoro-4-(4-methoxyphenyl)-1-phenylazetidin-2-one
approved: f
ligand name: NCRW0005-F05
type: SyntheticOrganicLigand

(R)-Ro65-6570
in ch i key: BBOAHBVXCYBKLC-JOCHJYFZSA-N
in ch i: InChI=1S/C25H25N3O/c29-24-25(28(17-26-24)20-9-2-1-3-10-20)12-14-27(15-13-25)22-16-19-8-4-6-18-7-5-11-21(22)23(18)19/h1-11,22H,12-17H2,(H,26,29)/t22-/m1/s1
comment: NOP receptor agonist.
iupac name: 8-[(1R)-1,2-dihydroacenaphthylen-1-yl]-1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one
xref: CHEMBL355202
synonym: (R)-Ro 65-6570
approved: f
ligand name: (R)-Ro65-6570
type: SyntheticOrganicLigand

dubermatinib
in ch i key: YUAALFPUEOYPNX-UHFFFAOYSA-N
comment: Dubermatinib (TP-0903) is an inhibitor of the TAM family receptor tyrosine kinase AXL and it is being investigated for its antineoplastic activity <Reference id=22625/><Reference id=29976/>, in particular against pancreatic cancer and lymphocytic leukemias (in combination with <Ligand id=6912/> or other antineoplastic drugs).
iupac name: 2-((5-chloro-2-((4-((4-methylpiperazin-1-yl)methyl)phenyl)amino)pyrimidin-4-yl)amino)-N,N-dimethylbenzenesulfonamide
xref: CHEMBL2022968
synonym: TP-0903
synonym: TP 0903
synonym: TP0903
synonym: compound 13
approved: f
ligand name: dubermatinib
type: SyntheticOrganicLigand

BLU-9931
in ch i key: TXEBNKKOLVBTFK-UHFFFAOYSA-N
comment: BLU-9931 is a selective and irreversible (covalent) inhibitor of the receptor tyrosine kinase, fibroblast growth factor receptor 4 (FGFR4) <Reference id=29975/>. The compound is being investigated for its anti-tumour action in hepatocellular carcinomas (HCC) where the fibroblast growth factor 19 (FGF19)/FGFR4 signaling pathway is activated by genetic alteration.
iupac name: N-[2-[[6-(2,6-dichloro-3,5-dimethoxyphenyl)quinazolin-2-yl]amino]-3-methylphenyl]prop-2-enamide
synonym: BLU9931
approved: f
ligand name: BLU-9931
type: SyntheticOrganicLigand

compound 1j [PMID: 26314925]
in ch i key: CZAFIFBJBFDMTP-UHFFFAOYSA-N
comment: Compound 1j is the most potent inhibitor of sphingomyelin synthase 1 (SMS1; SGMS1) reported in <Reference id=29917/>.
iupac name: N-[(4-bromophenyl)methyl]-2-{4-[(2-phenylethyl)sulfamoyl]phenoxy}acetamide
approved: f
ligand name: compound 1j [PMID: 26314925]
type: SyntheticOrganicLigand

polybia-MP1
in ch i key: WQWSKHPVGKVCQT-KXOXSZQSSA-N
comment: This is a mastoparan (PubChem CID 6324633) type peptide toxin isolated from the venom of the Brazilian wasp, Polybia paulista, with reported antimicrobial <Reference id=29971/> and anti-cancer effects <Reference id=29973/><Reference id=29972/><Reference id=29970/>. The N-terminal aspartic acid residue at position 2 of this peptide is important for the peptide's interaction with anionic vesicles in vitro <Reference id=29969/>.
synonym: MP-1
approved: f
ligand name: polybia-MP1
type: PeptideLigand

aminoethoxyvinylglycine
canonical SMILES: NC(C(=O)O)C=COCCN
isomeric SMILES: N[C@H](C(=O)O)/C=C/OCCN
in ch i key: USGUVNUTPWXWBA-JRIXXDKMSA-N
in ch i: InChI=1S/C6H12N2O3/c7-2-4-11-3-1-5(8)6(9)10/h1,3,5H,2,4,7-8H2,(H,9,10)/b3-1+/t5-/m0/s1
comment: Inhibitor of cystathionine γ-lyase (CSE). This compound is commonly used as its hydrochloride salt, AVG-HCl (PubChem CID 16211101).
iupac name: (E,2S)-2-amino-4-(2-aminoethoxy)but-3-enoic acid
xref: CHEMBL1619821
synonym: aviglycine
approved: f
ligand name: aminoethoxyvinylglycine
type: SyntheticOrganicLigand

β-Cyano-L-alanine
canonical SMILES: NC(C(=O)O)CC#N
isomeric SMILES: N[C@H](C(=O)O)CC#N
in ch i key: BXRLWGXPSRYJDZ-VKHMYHEASA-N
in ch i: InChI=1S/C4H6N2O2/c5-2-1-3(6)4(7)8/h3H,1,6H2,(H,7,8)/t3-/m0/s1
comment: Inhibitor of cystathionine γ-lyase (CSE).
iupac name: (2S)-2-amino-3-cyanopropanoic acid
synonym: 3-Cyano-L-alanine
synonym: L-beta-Cyanoalanine
approved: f
ligand name: β-Cyano-L-alanine
type: SyntheticOrganicLigand

fosbretabulin
isomeric SMILES: COc1cc(/C=C/c2ccc(c(c2)OP(=O)(O)O)OC)cc(c1OC)OC
in ch i key: WDOGQTQEKVLZIJ-WAYWQWQTSA-N
in ch i: InChI=1S/C18H21O8P/c1-22-14-8-7-12(9-15(14)26-27(19,20)21)5-6-13-10-16(23-2)18(25-4)17(11-13)24-3/h5-11H,1-4H3,(H2,19,20,21)/b6-5-
comment: Fosbretabulin is being investigated for anti-tumour potential. It interferes with vascularisation by preventing tubulin-polymerisation and disrupting cell junctions <Reference id=44103/>. This action destroys tumour vasculature and leads to cancer cell death and necrosis. Mechanistically, fosbretabulin is dephosphorylated to the active tubulin polymerisation inhibitor <Ligand id=8854/> <Reference id=29961/>. The compound was originally isolated from the African bush willow (Combretum caffrum) <Reference id=29960/><Reference id=29958/>.
iupac name: [2-methoxy-5-[(Z)-2-(3,4,5-trimethoxyphenyl)ethenyl]phenyl] dihydrogen phosphate
xref: CHEMBL1206232
synonym: CA4DP
synonym: fosbretabulin disodium
synonym: fosbretabulin tromethamine
synonym: combretastatin A4 phosphate
synonym: Zybrestat (fosbretabulin disodium)
approved: f
ligand name: fosbretabulin
type: SyntheticOrganicLigand

compound 8a [PMID: 23713581]
canonical SMILES: CCCNC(=O)COc1ccc(cc1)c1oc2c(c1C#Cc1cccc(c1)Cl)cc(c(c2)O)C(=O)O
isomeric SMILES: CCCNC(=O)COc1ccc(cc1)c1oc2c(c1C#Cc1cccc(c1)Cl)cc(c(c2)O)C(=O)O
in ch i key: ZAKVHDWXAFAMTH-UHFFFAOYSA-N
in ch i: InChI=1S/C28H22ClNO6/c1-2-12-30-26(32)16-35-20-9-7-18(8-10-20)27-21(11-6-17-4-3-5-19(29)13-17)22-14-23(28(33)34)24(31)15-25(22)36-27/h3-5,7-10,13-15,31H,2,12,16H2,1H3,(H,30,32)(H,33,34)
comment: Compound 8a was designed as a small-molecule inhibitor of the lymphoid-specific non-receptor tyrosine phosphatase, LYP (PTPN22) <Reference id=29955/>. PTPN22 directly dephosphorylates several kinase enzymes, effecting negative regulation of T-cell receptor (TCR) signaling <Reference id=29956/>, and is implicated in autoimmune diseases <Reference id=29957/>.
iupac name: 3-[2-(3-chlorophenyl)ethynyl]-6-hydroxy-2-[4-[2-oxo-2-(propylamino)ethoxy]phenyl]-1-benzofuran-5-carboxylic acid
xref: CHEMBL2396718
approved: f
ligand name: compound 8a [PMID: 23713581]
type: SyntheticOrganicLigand

SM-122
in ch i key: XBTLZUHJBOBKRG-HCUBDLJJSA-N
in ch i: InChI=1S/C28H36N4O3/c1-19(29-2)26(33)30-23-16-10-9-15-22-17-18-24(32(22)28(23)35)27(34)31-25(20-11-5-3-6-12-20)21-13-7-4-8-14-21/h3-8,11-14,19,22-25,29H,9-10,15-18H2,1-2H3,(H,30,33)(H,31,34)/t19-,22-,23-,24-/m0/s1
comment: SM-122 is an inhibitor of the inhibitor of apoptosis proteins (IAPs) <Reference id=25463/>.
iupac name: (3S,6S,10aS)-N-benzhydryl-6-[[(2S)-2-(methylamino)propanoyl]amino]-5-oxo-2,3,6,7,8,9,10,10a-octahydro-1H-pyrrolo[1,2-a]azocine-3-carboxamide
xref: CHEMBL481422
synonym: Smac peptide mimetic 20
synonym: compound 1
approved: f
ligand name: SM-122
type: SyntheticOrganicLigand

combretastatin A4
canonical SMILES: COc1cc(C=Cc2ccc(c(c2)O)OC)cc(c1OC)OC
isomeric SMILES: COc1cc(/C=C/c2ccc(c(c2)O)OC)cc(c1OC)OC
in ch i key: HVXBOLULGPECHP-WAYWQWQTSA-N
in ch i: InChI=1S/C18H20O5/c1-20-15-8-7-12(9-14(15)19)5-6-13-10-16(21-2)18(23-4)17(11-13)22-3/h5-11,19H,1-4H3/b6-5-
comment: Combretastatin A4 is the active metabolite of 8857. Combretastatin A4 interacts with the colchicine binding site of tubulin, which primarily resides within the β-tubulin subunit, at its interface with the α-subunit <Reference id=29961/>. The compound has antineoplastic activity, inhibiting microtubule polymerization, and causing mitotic arrest and apoptosis, particularly targeting the tumour vasculature <Reference id=29959/>.
iupac name: 2-methoxy-5-[(Z)-2-(3,4,5-trimethoxyphenyl)ethenyl]phenol
xref: CHEMBL67
synonym: CA-4
synonym: NSC-613729
synonym: combretastatin A-4
synonym: combretastatin A4
approved: f
ligand name: combretastatin A4
type: SyntheticOrganicLigand

yzm18
in ch i key: CYOSFMPARINMQP-DRFTYPOQSA-N
in ch i: InChI=1S/C28H48N6O11S/c1-7-16(4)24(30-17(5)36)28(43)34-21(14-35)27(42)32-19(8-9-22(29)37)25(40)33-20(12-15(2)3)26(41)31-18(13-23(38)39)10-11-46(6,44)45/h10-11,15-16,18-21,24,35H,7-9,12-14H2,1-6H3,(H2,29,37)(H,30,36)(H,31,41)(H,32,42)(H,33,40)(H,34,43)(H,38,39)/b11-10+/t16-,18+,19-,20-,21-,24-/m0/s1
comment: Yzm18 is an inhibitor of the threonine aspartase, taspase 1 (TASP1), with its structure based on that of the preferred enzyme cleavage site Ac-Ile-Ser-Gln-Leu-Asp.
iupac name: (E,3S)-3-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S,3S)-2-acetamido-3-methylpentanoyl]amino]-3-hydroxypropanoyl]amino]-5-amino-5-oxopentanoyl]amino]-4-methylpentanoyl]amino]-5-methylsulfonylpent-4-enoic acid
xref: CHEMBL570714
approved: f
ligand name: yzm18
type: SyntheticOrganicLigand

compound 4d [PMID: 20655626]
canonical SMILES: COc1ccc2c(c1)CCC(C2=O)Cc1ccccc1Br
isomeric SMILES: COc1ccc2c(c1)CCC(C2=O)Cc1ccccc1Br
in ch i key: GKGZPFKBDIIBHB-UHFFFAOYSA-N
in ch i: InChI=1S/C18H17BrO2/c1-21-15-8-9-16-12(11-15)6-7-14(18(16)20)10-13-4-2-3-5-17(13)19/h2-5,8-9,11,14H,6-7,10H2,1H3
comment: Compound 4d is one of a series of compounds designed to identify inhibitors of CYP24A1, an enzyme which metabolises <Ligand id=2779/> (calcitriol), but in fact exhibits preferential inhibition of the sterol 27-hydroxylase enzyme, CYP27A1 <Reference id=29947/>.
iupac name: 2-[(2-bromophenyl)methyl]-6-methoxy-3,4-dihydro-2H-naphthalen-1-one
xref: CHEMBL1253946
approved: f
ligand name: compound 4d [PMID: 20655626]
type: SyntheticOrganicLigand

17-octadecynoic acid
canonical SMILES: C#CCCCCCCCCCCCCCCCC(=O)O
isomeric SMILES: C#CCCCCCCCCCCCCCCCC(=O)O
in ch i key: DZIILFGADWDKMF-UHFFFAOYSA-N
in ch i: InChI=1S/C18H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h1H,3-17H2,(H,19,20)
comment: 17-octadecynoic acid inhibits activity of the leukotriene B4 (LTB4) ω-hydroxylase (CYP4F2) <Reference id=29945/>.
iupac name: octadec-17-ynoic acid
xref: CHEMBL182310
synonym: 17-ODYA
approved: f
ligand name: 17-octadecynoic acid
type: SyntheticOrganicLigand

bromfenac
canonical SMILES: OC(=O)Cc1cccc(c1N)C(=O)c1ccc(cc1)Br
isomeric SMILES: OC(=O)Cc1cccc(c1N)C(=O)c1ccc(cc1)Br
in ch i key: ZBPLOVFIXSTCRZ-UHFFFAOYSA-N
in ch i: InChI=1S/C15H12BrNO3/c16-11-6-4-9(5-7-11)15(20)12-3-1-2-10(14(12)17)8-13(18)19/h1-7H,8,17H2,(H,18,19)
comment: Bromfenac is a nonsteroidal anti-inflammatory drug (NSAID). Marketed formulations may contain bromfenac sodium (PubChem CID 23693301).
iupac name: 2-[2-amino-3-(4-bromobenzoyl)phenyl]acetic acid
xref: CHEMBL1077
synonym: AHR-10282B
synonym: Bromday®
synonym: Xibrom®
synonym: Prolensa®
approved: t
ligand name: bromfenac
type: SyntheticOrganicLigand

compound 7b [Haftchenary et al., 2013]
in ch i key: JOFDSYLCZIHGGO-UHFFFAOYSA-N
in ch i: InChI=1S/C35H39N3O6S/c1-36(2)31-13-7-12-29-28(31)11-8-14-33(29)45(43,44)37(3)23-34(40)38(27-19-20-30(35(41)42)32(39)21-27)22-24-15-17-26(18-16-24)25-9-5-4-6-10-25/h7-8,11-21,25,39H,4-6,9-10,22-23H2,1-3H3,(H,41,42)
comment: Compound 7b was identified in a screening study to find inhibitors of the non-receptor type tyrosine phosphatase PTP1B (HGNC gene symbol PTPN1) <Reference id=29944/>. PTPN1 inhibitors have been scrutinised for anti-type 2 diabetes potential.
iupac name: 4-[(4-cyclohexylphenyl)methyl-[2-[[5-(dimethylamino)naphthalen-1-yl]sulfonyl-methylamino]acetyl]amino]-2-hydroxybenzoic acid
xref: CHEMBL1829872
approved: f
ligand name: compound 7b [Haftchenary et al., 2013]
type: SyntheticOrganicLigand

compound D24 [PMID: 24374347]
canonical SMILES: N#CC(c1ccccc1OCc1ccccc1)Nc1ccccc1OC
isomeric SMILES: N#CC(c1ccccc1OCc1ccccc1)Nc1ccccc1OC
in ch i key: KYFXPHPBTUJULU-UHFFFAOYSA-N
in ch i: InChI=1S/C22H20N2O2/c1-25-22-14-8-6-12-19(22)24-20(15-23)18-11-5-7-13-21(18)26-16-17-9-3-2-4-10-17/h2-14,20,24H,16H2,1H3
comment: Compound D24 is the most potent inhibitor of sphingomyelin synthase 2 (SMS2; SGMS2) reported in <Reference id=29912/>.
iupac name: 2-[(2-methoxyphenyl)amino]-2-[2-(phenylmethoxy)phenyl]acetonitrile
xref: CHEMBL1509437
approved: f
ligand name: compound D24 [PMID: 24374347]
type: SyntheticOrganicLigand

compound 9 [PMID: 11606127]
in ch i key: XBGCSAANSNGXGH-UHFFFAOYSA-N
in ch i: InChI=1S/C18H20N4O2S/c1-14(2)22(25(23,24)17-10-8-15(19)9-11-17)18-12-13-20-21(18)16-6-4-3-5-7-16/h3-14H,19H2,1-2H3
comment: Compound 9 is one of the sulfaphenazole derivatives designed in a study to identify selective inhibitors for cytochrome P450 enzymes of the 2C subfamily <Reference id=29911/>.
iupac name: 4-amino-N-(2-phenylpyrazol-3-yl)-N-propan-2-ylbenzenesulfonamide
xref: CHEMBL121323
approved: f
ligand name: compound 9 [PMID: 11606127]
type: SyntheticOrganicLigand

peptide ligand 2 [PMID: 19055415]
in ch i key: VALZMCWLPCJDLL-KXXTWUBKSA-N
comment: Peptide ligand 2 has amino acid sequence cdGTyr(3-NO2)GBNc, where B=hydroxyproline <Reference id=29943/>.
synonym: LXY3
synonym: (cdGTyr(3-NO2)GBNc
approved: f
ligand name: peptide ligand 2 [PMID: 19055415]
type: PeptideLigand

SCH-900229
in ch i key: AMXSRXZYBDALJG-XERREHJYSA-N
comment: SCH-900229 is a presinilin (PS) inhibitor <Reference id=29942/>.
iupac name: (4S,4aS,10bS)-10b-(4-chlorophenyl)sulfonyl-7,10-difluoro-4-(2-methylsulfonylethyl)-2,4,4a,5-tetrahydro-1H-pyrano[3,4-c]chromene
xref: CHEMBL2159511
synonym: SCH 900229
synonym: SCH900229
approved: f
ligand name: SCH-900229
type: SyntheticOrganicLigand

inhibitor A [PMID: 12482429]
in ch i key: KQPGDBVGEXAZAW-UKILVPOCSA-N
in ch i: InChI=1S/C26H44F2NO5P/c1-2-3-4-5-6-7-8-9-10-11-12-13-17-20-24(30)29-23(21-26(27,28)35(32,33)34)25(31)22-18-15-14-16-19-22/h14-16,18-19,23,25,31H,2-13,17,20-21H2,1H3,(H,29,30)(H2,32,33,34)/t23-,25+/m0/s1
comment: This compound is an analogue of N-palmitoylsphingosine-1-phosphate and it inhibits neutral sphingomyelinase in vitro <Reference id=29941/>.
iupac name: [(3S,4R)-1,1-difluoro-3-(hexadecanoylamino)-4-hydroxy-4-phenylbutyl]phosphonic acid
xref: CHEMBL310981
approved: f
ligand name: inhibitor A [PMID: 12482429]
type: SyntheticOrganicLigand

CGS-27023A
in ch i key: BSIZUMJRKYHEBR-QGZVFWFLSA-N
in ch i: InChI=1S/C18H23N3O5S/c1-13(2)17(18(22)20-23)21(12-14-5-4-10-19-11-14)27(24,25)16-8-6-15(26-3)7-9-16/h4-11,13,17,23H,12H2,1-3H3,(H,20,22)/t17-/m1/s1
comment: CGS-27023A is reported as a potent pan-inhibitor of matrix metalloproteinases <Reference id=29938/>. Note that CGS-27023A imay be used experimentally as the hydrochloride salt (PubChem CID 9888897).
iupac name: (2R)-N-hydroxy-2-[(4-methoxyphenyl)sulfonyl-(pyridin-3-ylmethyl)amino]-3-methylbutanamide
xref: CHEMBL267178
synonym: CGS 27023A
synonym: CGS27023A
synonym: MMI270
approved: f
ligand name: CGS-27023A
type: SyntheticOrganicLigand

S-4048
in ch i key: MYXPHMOLFCUDIL-MLFVSVOESA-N
in ch i: InChI=1S/C32H30ClN3O7/c33-22-10-8-19(9-11-22)23-13-21(23)17-42-32(31(40)41)15-26(37)29(39)27(16-32)43-28(38)14-25(20-5-2-1-3-6-20)36-18-35-30-24(36)7-4-12-34-30/h1-12,14,18,21,23,26-27,29,37,39H,13,15-17H2,(H,40,41)/b25-14-/t21-,23+,26+,27+,29+,32-/m0/s1
comment: S-4048 is a chlorogenic acid (PubChem CID 1794427) derivative which acts as a very potent inhibitor of glucose-6-phosphate translocase (G6P T1; SLC37A4). SLC37A4 acts as a gatekeeper to transport glucose 6-phosphate into the endoplasmic reticulum and therefore plays an important role in the regulation of blood glucose levels.
iupac name: (1S,3R,4R,5R)-1-[[(1R,2S)-2-(4-chlorophenyl)cyclopropyl]methoxy]-3,4-dihydroxy-5-[(Z)-3-imidazo[4,5-b]pyridin-1-yl-3-phenylprop-2-enoyl]oxycyclohexane-1-carboxylic acid
xref: CHEMBL236247
synonym: S 4048
approved: f
ligand name: S-4048
type: SyntheticOrganicLigand

compound 5 [Noble et al., 1992]
in ch i key: OEKHZIJBKVQWQC-UHFFFAOYSA-N
in ch i: InChI=1S/C6H15O13P3S2/c7-1-2(8)5(18-21(13,14)23)6(19-22(15,16)24)3(9)4(1)17-20(10,11)12/h1-9H,(H2,10,11,12)(H2,13,14,23)(H2,15,16,24)
comment: Compound 5 is a non-hydrolysable phosphorothioates analogue of inositol phosphate 3 (IP3) <Reference id=29936/>. As such this compound would be expected to behave as a substrate for IP3 metabolising inositol polyphosphate-5-phosphatase enzymes, with a negative effect on enzyme activity, and effect sustained release of intracellular calcium. Note that we show the sugar moiety without stereochemistry.
iupac name: [3,4-bis(dihydroxyphosphinothioyloxy)-2,5,6-trihydroxycyclohexyl] dihydrogen phosphate
xref: CHEMBL1161242
synonym: myo-inositol 1-phosphate 4,5-bisphosphorothioate
approved: f
ligand name: compound 5 [Noble et al., 1992]
type: SyntheticOrganicLigand

compound 5 [PMID: 10869194]
in ch i key: NOTLGMDYQMIWNO-ZBFFZJPBSA-N
in ch i: InChI=1S/C39H54O5/c1-24-15-20-38(34(43)44)21-22-39(23-28(41)12-9-26-7-10-27(40)11-8-26)29(33(38)25(24)2)13-14-31-36(5)18-17-32(42)35(3,4)30(36)16-19-37(31,39)6/h7-13,24-25,30-33,40,42H,14-23H2,1-6H3,(H,43,44)/b12-9+/t24-,25+,30+,31-,32+,33+,36+,37-,38+,39+/m1/s1
comment: Compound 5 is a pentacyclic triterpene ester isolated from Uncaria rhynchophylla, a plant used in traditional medicine by various indigenous cultures. Compound 5 is reported to inhibit phospholipase C-gamma 1 (PLCG1) <Reference id=29930/>.
iupac name: (1S,2R,4aS,6aR,6aR,6bR,8aR,10S,12aR,14bS)-10-hydroxy-6a-[(E)-4-(4-hydroxyphenyl)-2-oxobut-3-enyl]-1,2,6b,9,9,12a-hexamethyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydro-1H-picene-4a-carboxylic acid
xref: CHEMBL503874
approved: f
ligand name: compound 5 [PMID: 10869194]
type: NaturalProductLigand

compound 35 [PMID: 23916259]
in ch i key: YOOLXKXFWTXRHM-UHFFFAOYSA-N
in ch i: InChI=1S/C26H27N5O2/c32-20-9-7-19(8-10-20)28-23-24-27-14-15-31(24)22-16-17(6-11-21(22)29-23)25(33)30-26(12-13-26)18-4-2-1-3-5-18/h1-6,11,14-16,19-20,32H,7-10,12-13H2,(H,28,29)(H,30,33)
comment: Compound 35 is reported as an inhibitor of mitogen-activated protein kinase 8 (JNK1; MAPK8) <Reference id=29928/>.
iupac name: 4-[(4-hydroxycyclohexyl)amino]-N-(1-phenylcyclopropyl)imidazo[1,2-a]quinoxaline-8-carboxamide
xref: CHEMBL2420572
approved: f
ligand name: compound 35 [PMID: 23916259]
type: SyntheticOrganicLigand

4-acryloylphenol
canonical SMILES: C=CC(=O)c1ccc(cc1)O
isomeric SMILES: C=CC(=O)c1ccc(cc1)O
in ch i key: NKPPNPJUBLEKAD-UHFFFAOYSA-N
in ch i: InChI=1S/C9H8O2/c1-2-9(11)7-3-5-8(10)6-4-7/h2-6,10H,1H2
comment: 4-acryloylphenol inhibits GABA transaminase (GABA-T; ABAT) and succinic semialdehyde dehydrogenase (SSADH; ALDH5A1) <Reference id=29927/>.
iupac name: 1-(4-hydroxyphenyl)prop-2-en-1-one
xref: CHEMBL378577
synonym: compound 6
approved: f
ligand name: 4-acryloylphenol
type: SyntheticOrganicLigand

compound 7a [PMID: 24884590]
in ch i key: LBKIJSKRXVUWER-UHFFFAOYSA-N
in ch i: InChI=1S/C25H20F3NO3/c26-25(27,28)19-7-1-4-16(12-19)13-20-15-22-21(8-3-9-23(22)32-20)17-5-2-6-18(14-17)24(31)29-10-11-30/h1-9,12,14-15,30H,10-11,13H2,(H,29,31)
comment: Compound 7a is reported as an agonist of the orphan GPCR, GPR52 <Reference id=28256/>.
iupac name: N-(2-hydroxyethyl)-3-[2-[[3-(trifluoromethyl)phenyl]methyl]-1-benzofuran-4-yl]benzamide
xref: CHEMBL3299119
approved: f
ligand name: compound 7a [PMID: 24884590]
type: SyntheticOrganicLigand

torin 2
in ch i key: GUXXEUUYCAYESJ-UHFFFAOYSA-N
in ch i: InChI=1S/C24H15F3N4O/c25-24(26,27)17-2-1-3-18(11-17)31-22(32)9-6-16-13-29-20-7-4-14(10-19(20)23(16)31)15-5-8-21(28)30-12-15/h1-13H,(H2,28,30)
comment: Torin 2 is reported as a potent and selective inhibitor of the serine/threonine kinase, mTOR (mechanistic target of rapamycin) <Reference id=29926/>.
iupac name: 9-(6-aminopyridin-3-yl)-1-[3-(trifluoromethyl)phenyl]benzo[h][1,6]naphthyridin-2-one
xref: CHEMBL1765602
synonym: Torin-2
synonym: torin2
synonym: compound 3
approved: f
ligand name: torin 2
type: SyntheticOrganicLigand

compound 10 [PMID: 18759424]
in ch i key: DIXYWCRPNNUEHU-XBXARRHUSA-N
in ch i: InChI=1S/C27H29ClO3/c1-25-11-18-12-26(2,14-25)16-27(13-18,15-25)21-10-19(5-7-23(21)29)20-6-3-17(9-22(20)28)4-8-24(30)31/h3-10,18,29H,11-16H2,1-2H3,(H,30,31)/b8-4+
comment: Compound 10 is one of the most potent inhibitors of SHP (NR0B2) reported in <Reference id=29925/>.
iupac name: (E)-3-[3-chloro-4-[3-(3,5-dimethyl-1-adamantyl)-4-hydroxyphenyl]phenyl]prop-2-enoic acid
xref: CHEMBL461415
synonym: 3-Cl-AHPC analogue 10
approved: f
ligand name: compound 10 [PMID: 18759424]
type: SyntheticOrganicLigand

bretylium
canonical SMILES: CC[N+](Cc1ccccc1Br)(C)C
isomeric SMILES: CC[N+](Cc1ccccc1Br)(C)C
in ch i key: AAQOQKQBGPPFNS-UHFFFAOYSA-N
in ch i: InChI=1S/C11H17BrN/c1-4-13(2,3)9-10-7-5-6-8-11(10)12/h5-8H,4,9H2,1-3H3/q+1
comment: Bretylium is a substrate for the noradrenaline transporter so it accumulates inside nerve terminals which have this transporter. This accumulation underlies its inhibitory action on the sympathetic nervous system. Bretylium tosylate is no longer available in the US.
xref: CHEMBL1199080
synonym: ASL-603
synonym: bretylium tosylate
synonym: Bretylol®
approved: t
ligand name: bretylium
type: SyntheticOrganicLigand

compound 16 [PMID: 19097778]
in ch i key: ONBQEOIKXPHGMB-VBSBHUPXSA-N
in ch i: InChI=1S/C20H22O9/c21-9-16-18(26)19(27)20(29-16)28-15-8-12(23)7-14(25)17(15)13(24)6-3-10-1-4-11(22)5-2-10/h1-2,4-5,7-8,16,18-23,25-27H,3,6,9H2/t16-,18-,19-,20-/m1/s1
comment: Compound 16 is the highest potency inhibitor of the human concentrative nucleoside transporter 3 (CNT3; SLC28A3) reported in <Reference id=29923/>.
iupac name: 1-[2-[(2S,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-4,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)propan-1-one
xref: CHEMBL482331
approved: f
ligand name: compound 16 [PMID: 19097778]
type: SyntheticOrganicLigand

compound 4 [PMID: 16495056]
in ch i key: PBIBEWTURATALQ-UHFFFAOYSA-N
in ch i: InChI=1S/C31H37NO2/c1-2-10-25-16-18-26(19-17-25)30(33)15-9-22-32-23-20-29(21-24-32)31(34,27-11-5-3-6-12-27)28-13-7-4-8-14-28/h3-8,11-14,16-19,29,34H,2,9-10,15,20-24H2,1H3
comment: This compound is a <Ligand id=2608/> analogue. It is reported as a useful tool compound (pharmacological inhibitor) for investigating the function of human cytochrome P450 2J2 <Reference id=29910/>.
iupac name: 4-[4-[hydroxy-di(phenyl)methyl]piperidin-1-yl]-1-(4-propylphenyl)butan-1-one
xref: CHEMBL208528
approved: f
ligand name: compound 4 [PMID: 16495056]
type: SyntheticOrganicLigand

compound 1 [PMID: 21882820]
canonical SMILES: OC(=O)c1sccc1SCc1ccc(c(c1)Cl)Cl
isomeric SMILES: OC(=O)c1sccc1SCc1ccc(c(c1)Cl)Cl
in ch i key: UCHDVTOVFHVWOS-UHFFFAOYSA-N
in ch i: InChI=1S/C12H8Cl2O2S2/c13-8-2-1-7(5-9(8)14)6-18-10-3-4-17-11(10)12(15)16/h1-5H,6H2,(H,15,16)
comment: Compound 1 is reported to inhibit receptor protein tyrosine phosphatase γ (RPTPγ; PTPRG) <Reference id=29908/>.
iupac name: 3-[(3,4-dichlorophenyl)methylsulfanyl]thiophene-2-carboxylic acid
xref: CHEMBL1403981
approved: f
ligand name: compound 1 [PMID: 21882820]
type: SyntheticOrganicLigand

compound 2e [PMID: 19013076]
canonical SMILES: NC(=NCCCC(C(=O)O)N)CC=C
isomeric SMILES: NC(=NCCC[C@@H](C(=O)O)N)CC=C
in ch i key: LMDRHVQXMBGSGU-ZETCQYMHSA-N
in ch i: InChI=1S/C9H17N3O2/c1-2-4-8(11)12-6-3-5-7(10)9(13)14/h2,7H,1,3-6,10H2,(H2,11,12)(H,13,14)/t7-/m0/s1
comment: Compound 2a is an inhibitor of human dimethylarginine dimethylaminohydrolase 1 (DDAH1), reported in <Reference id=29909/>. However, a lack of selectivity of 2a over NOSs activity, limits its clinical utility. Compound 3a (PubChem CID 11413609) is identified as the most useful human DDAH1 inhibitor in this series as it exhibits little inhibition of NOS enzyme activity.
iupac name: (2S)-2-amino-5-(1-aminobut-3-enylideneamino)pentanoic acid
xref: CHEMBL106820
synonym: vinyl-L-NIO
synonym: L-VNIO
approved: f
ligand name: compound 2e [PMID: 19013076]
type: SyntheticOrganicLigand

compound 2 [PMID: 22380603]
in ch i key: HQWXZTRYIWULAX-UHFFFAOYSA-N
in ch i: InChI=1S/C24H25N5O7S/c1-4-6-17-20-21(29(3)27-17)23(31)26-22(25-20)16-12-14(8-10-19(16)36-5-2)37(34,35)28-13-7-9-18(30)15(11-13)24(32)33/h7-12,28,30H,4-6H2,1-3H3,(H,32,33)(H,25,26,31)
comment: Compound 2 is a <Ligand id=4743/> analogue, with inhibitory activity against the human ATP binding cassette (ABC) transporter ABCC5 <Reference id=29905/>, a protein which reportedly transports cGMP out of cells <Reference id=29906/>.
iupac name: 5-[[4-ethoxy-3-(1-methyl-7-oxo-3-propyl-4H-pyrazolo[5,4-e]pyrimidin-5-yl)phenyl]sulfonylamino]-2-hydroxybenzoic acid
xref: CHEMBL1338248
approved: f
ligand name: compound 2 [PMID: 22380603]
type: SyntheticOrganicLigand

compound 7b [PMID: 17583500]
in ch i key: PHVXTQIROLEEDB-UHFFFAOYSA-N
in ch i: InChI=1S/C32H38ClN3O/c1-24-7-2-4-10-30(24)28-9-6-19-35(23-28)22-25-12-14-27(15-13-25)32(37)36(29-16-18-34-21-29)20-17-26-8-3-5-11-31(26)33/h2-5,7-8,10-15,28-29,34H,6,9,16-23H2,1H3
comment: Compound 7b is the most potent inhibitor of membrane-bound transcription factor peptidase, site 1 (MBTPS1) reported in <Reference id=29903/>. PF-429242 (compound 1u; PubChem CID 23661637) is also reported, and although this has lower potency against enzyme activity it has favourble drug-like qualities and is active in vivo <Reference id=29904/>.
iupac name: N-[2-(2-chlorophenyl)ethyl]-4-[[3-(2-methylphenyl)piperidin-1-yl]methyl]-N-pyrrolidin-3-ylbenzamide
xref: CHEMBL391935
approved: f
ligand name: compound 7b [PMID: 17583500]
type: SyntheticOrganicLigand

compound 11j [PMID: 23021994]
in ch i key: RZFJBSIAXYEPBX-UHFFFAOYSA-N
comment: Compound 11j is reported as one of the lead compounds in the search for selective inhibitors of human SMG1 kinase (SMG1 phosphatidylinositol 3-kinase-related kinase) <Reference id=29898/>.
iupac name: 1-[4-[4-[2-[4-chloro-3-(diethylsulfamoyl)anilino]pyrimidin-4-yl]pyridin-2-yl]phenyl]-3-methylurea
xref: CHEMBL2158866
approved: f
ligand name: compound 11j [PMID: 23021994]
type: SyntheticOrganicLigand

disprocynium24
isomeric SMILES: CC([n+]1ccc(c2c1cccc2)/C=c/1/ccc2c(n1C(C)C)cccc2)C
in ch i key: TYFOKKOWQOKKCH-UHFFFAOYSA-N
in ch i: InChI=1S/C25H27N2/c1-18(2)26-16-15-21(23-10-6-8-12-25(23)26)17-22-14-13-20-9-5-7-11-24(20)27(22)19(3)4/h5-19H,1-4H3/q+1
comment: Disprocynium24 inhibits extraneuronal monoamine transport, facilitated by the organic cation transporter 3 (OCT3; SLC22A3) <Reference id=29896/><Reference id=29897/>.
iupac name: (2E)-1-propan-2-yl-2-[(1-propan-2-ylquinolin-1-ium-4-yl)methylidene]quinoline
xref: CHEMBL339858
synonym: 1,1'-Diisopropyl-2,4'-cyanine
approved: f
ligand name: disprocynium24
type: SyntheticOrganicLigand

compound III [PMID: 24080463]
in ch i key: QROCYVPJPWZLIK-UHFFFAOYSA-N
in ch i: InChI=1S/C40H70N4O4/c1-9-41(10-2)25-29-45-37-23-21-35(33-39(37)47-31-27-43(13-5)14-6)19-17-18-20-36-22-24-38(46-30-26-42(11-3)12-4)40(34-36)48-32-28-44(15-7)16-8/h21-24,33-34H,9-20,25-32H2,1-8H3
comment: Compound III is a survivin (BIRC5) inhibitor such as reported in patent US20110014192 A1 <Reference id=29894/>. Compound III is a potential nordihydroguaiaretic acid (NDGA)-based anti-neoplastic agent <Reference id=29895/>.
iupac name: 2-[4-[4-[3,4-bis[2-(diethylamino)ethoxy]phenyl]butyl]-2-[2-(diethylamino)ethoxy]phenoxy]-N,N-diethylethanamine
xref: CHEMBL2442083
approved: f
ligand name: compound III [PMID: 24080463]
type: SyntheticOrganicLigand

compound 50 [PMID: 24313754]
in ch i key: MYFFGZYMLKZBPZ-UHFFFAOYSA-N
in ch i: InChI=1S/C21H22N6O3S/c1-14-22-23-21-17-6-4-3-5-16(17)20(24-27(14)21)15-7-8-19(26-9-11-30-12-10-26)18(13-15)25-31(2,28)29/h3-8,13,25H,9-12H2,1-2H3
comment: Compound 50 was identified in a study designed to find inhibitors of BET bromodomains in proteins outside of the BET subfamily <Reference id=29893/>. Compound 50 inhibits BET domain activity in several enzymes including cat eye syndrome chromosome region, candidate 2 (CECR2), CREB binding protein (CREBBP) and bromodomain containing 9 (BRD9).
xref: CHEMBL3108800
approved: f
ligand name: compound 50 [PMID: 24313754]
type: SyntheticOrganicLigand

compound 2 [Maurer et al., 2012]
isomeric SMILES: C=CCN1C(=S)NC(=O)/C(=C/c2ccc(o2)c2cccc(c2Cl)Cl)/C1=O
in ch i key: NASLGRREAVKNNT-FMIVXFBMSA-N
comment: Compound 2 is an inhibitor of the NAD+-dependent histone deacetylase, sirtuin 5 (SIRT5) <Reference id=29892/>.
iupac name: (5E)-5-[[5-(2,3-dichlorophenyl)furan-2-yl]methylidene]-1-prop-2-enyl-2-sulfanylidene-1,3-diazinane-4,6-dione
xref: CHEMBL2203548
approved: f
ligand name: compound 2 [Maurer et al., 2012]
type: SyntheticOrganicLigand

TGN4
in ch i key: WSISVGWHSKNHQQ-JEWAQKBPSA-N
in ch i: InChI=1S/C42H66N2O14/c1-6-7-8-14-17-21-32(48)56-36-34-33(26(2)35(36)49)37-42(54,41(5,53)39(52)57-37)29(25-40(34,4)58-27(3)45)55-31(47)20-18-15-12-10-9-11-13-16-19-24-44-30(46)23-22-28(43)38(50)51/h28-29,34,36-37,53-54H,6-25,43H2,1-5H3,(H,44,46)(H,50,51)/t28?,29-,34+,36-,37-,40-,41+,42+/m0/s1
comment: TGN4 is a <Ligand id=5351/> analogue designed as an allosteric inhibitor of the sarcoplasmic/endoplasmic reticulum calcium-ATPase (SERCA) <Reference id=29890/>. Like thapsigargin, TGN4 disrupts calcium transport by binding to a hydrophobic pocket located in the transmembrane region of SERCA.
iupac name: 5-[[12-[[(3S,3aR,4S,6S,6aR,7S,9bS)-6-acetyloxy-3,3a-dihydroxy-3,6,9-trimethyl-7-octanoyloxy-2,8-dioxo-5,6a,7,9b-tetrahydro-4H-azuleno[4,5-b]furan-4-yl]oxy]-12-oxododecyl]amino]-2-amino-5-oxopentanoic acid
xref: CHEMBL365703
approved: f
ligand name: TGN4
type: SyntheticOrganicLigand

MT47-100
in ch i key: DMDAXRKDNRQTIF-UHFFFAOYSA-N
in ch i: InChI=1S/C21H15NO4/c23-18-4-2-1-3-15(18)13-7-5-12(6-8-13)14-9-10-17-16(11-14)19(24)20(25)21(26)22-17/h1-11,23,25H,(H2,22,24,26)
comment: MT47-100 modulates activity of the AMP-activated protein kinase (AMPK). The direction of modulation depends on the subunit composition of the enzyme. MT47-100 acts as a direct activator of β1 subunit-containing AMPK, and as an allosteric inhibitor of β2 subunit-containing AMPK <Reference id=29889/>.
iupac name: 6-[4-(2-hydroxyphenyl)phenyl]quinoline-2,3,4-triol
approved: f
ligand name: MT47-100
type: SyntheticOrganicLigand

CCT129957
canonical SMILES: O=C(c1cc2c([nH]1)c(ccc2)[N+](=O)[O-])NCCc1ccccc1
isomeric SMILES: O=C(c1cc2c([nH]1)c(ccc2)[N+](=O)[O-])NCCc1ccccc1
in ch i key: VXDJRTJBOJFUOC-UHFFFAOYSA-N
in ch i: InChI=1S/C17H15N3O3/c21-17(18-10-9-12-5-2-1-3-6-12)14-11-13-7-4-8-15(20(22)23)16(13)19-14/h1-8,11,19H,9-10H2,(H,18,21)
comment: CCT129957 is one of the hit PLCγ2 inhibitors verified experimentally, following a virtual HTS effort <Reference id=29888/>.
iupac name: 7-nitro-N-(2-phenylethyl)-1H-indole-2-carboxamide
xref: CHEMBL475789
approved: f
ligand name: CCT129957
type: SyntheticOrganicLigand

CTA091
in ch i key: FANCTJAFZSYTIS-IQUVVAJASA-N
in ch i: InChI=1S/C29H41NO3S/c1-20(15-17-34(30,33)25-9-5-4-6-10-25)26-13-14-27-22(8-7-16-29(26,27)3)11-12-23-18-24(31)19-28(32)21(23)2/h4-6,9-12,20,24,26-28,30-32H,2,7-8,13-19H2,1,3H3/b22-11+,23-12-/t20-,24-,26-,27+,28+,29-,34?/m1/s1
comment: Compound 3a is a vitamin D analogue designed to be a less calcemic inhibitor of cytochrome P450 enyme CYP24A1 <Reference id=29886/>. CYP24A1 regulates vitamin D levels and calcium homeostasis by initiating the degradation of physiologically active 1,25-dihydroxyvitamin D3 <Reference id=29887/>.
iupac name: (1R,3S,5Z)-5-[(2E)-2-[(1R,3aS,7aR)-7a-methyl-1-[(2R)-4-(phenylsulfonimidoyl)butan-2-yl]-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylidenecyclohexane-1,3-diol
xref: CHEMBL1627233
synonym: MK-24(S)-S(O)(NH)Ph
synonym: compound 3a [PMID: 15615534]
approved: f
ligand name: CTA091
type: SyntheticOrganicLigand

7ACC2
in ch i key: XTKDQPFUOFAMRL-UHFFFAOYSA-N
in ch i: InChI=1S/C18H15NO4/c1-19(11-12-5-3-2-4-6-12)14-8-7-13-9-15(17(20)21)18(22)23-16(13)10-14/h2-10H,11H2,1H3,(H,20,21)
comment: 7ACC2 is a lead entity identified as an inhibitor of lactate transport (uptake) mediated by the monocarboxylate transporter 4 (MCT4, SLC16A3) <Reference id=29885/>. It is hypothesised that inhibition of lactate flux in cancer cells will have a cytotoxic effect, by limiting their ability to fuel the TCA cycle.
iupac name: 7-[benzyl(methyl)amino]-2-oxochromene-3-carboxylic acid
xref: CHEMBL2442509
synonym: compound 19 [PMID: 24095010]
approved: f
ligand name: 7ACC2
type: SyntheticOrganicLigand

D-e-MAPP
canonical SMILES: CCCCCCCCCCCCCC(=O)NC(C(c1ccccc1)O)C
in ch i key: YLAZEWZHIRBZDA-NFBKMPQASA-N
in ch i: InChI=1S/C23H39NO2/c1-3-4-5-6-7-8-9-10-11-12-16-19-22(25)24-20(2)23(26)21-17-14-13-15-18-21/h13-15,17-18,20,23,26H,3-12,16,19H2,1-2H3,(H,24,25)/t20-,23-/m1/s1
comment: D-e-MAPP is an inhibitor of alkaline ceramidase activity <Reference id=29884/>.
iupac name: N-[(1S,2R)-1-hydroxy-1-phenylpropan-2-yl]tetradecanamide
xref: CHEMBL429926
synonym: D-erythro-MAPP
approved: f
ligand name: D-e-MAPP
type: SyntheticOrganicLigand

AKK(thioAc)LM21
in ch i key: IIESJRORKKINMK-SVXFZJLFSA-N
in ch i: InChI=1S/C28H53N7O6S2/c1-17(2)16-23(27(39)34-22(28(40)41)12-15-43-5)35-26(38)21(11-7-9-14-31-19(4)42)33-25(37)20(10-6-8-13-29)32-24(36)18(3)30/h17-18,20-23H,6-16,29-30H2,1-5H3,(H,31,42)(H,32,36)(H,33,37)(H,34,39)(H,35,38)(H,40,41)/t18-,20-,21-,22-,23-/m0/s1
comment: AKK(thioAc)LM21 (compound 3 in <Reference id=29883/>) is the most potent inhibitor of the deacetylase activity of SIRT6 reported in <Reference id=29883/>.
iupac name: (2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-6-amino-2-[[(2S)-2-aminopropanoyl]amino]hexanoyl]amino]-6-(ethanethioylamino)hexanoyl]amino]-4-methylpentanoyl]amino]-4-methylsulfanylbutanoic acid
xref: CHEMBL504711
approved: f
ligand name: AKK(thioAc)LM21
type: SyntheticOrganicLigand

compound 3 [Tuttle et al., 2013]
canonical SMILES: O=C1C(N)Cc2c(N1O)ccc(c2)Oc1ccccc1
isomeric SMILES: O=C1[C@@H](N)Cc2c(N1O)ccc(c2)Oc1ccccc1
in ch i key: COBQSWIQOSRUIK-ZDUSSCGKSA-N
in ch i: InChI=1S/C15H14N2O3/c16-13-9-10-8-12(20-11-4-2-1-3-5-11)6-7-14(10)17(19)15(13)18/h1-8,13,19H,9,16H2/t13-/m0/s1
comment: Compound 3 resulted from a SAR study to identify aminoadipate aminotransferase (KATII; AADAT; Q8N5Z0) inhibitors as potential therapeutics for the treatment of psychiatric and neurological disorders <Reference id=29882/>.
iupac name: (3S)-3-amino-1-hydroxy-6-phenoxy-3,4-dihydroquinolin-2-one
xref: CHEMBL2321944
approved: f
ligand name: compound 3 [Tuttle et al., 2013]
type: SyntheticOrganicLigand

compound 6b [PMID: 22749870]
in ch i key: KPKVFORNVZIISV-UHFFFAOYSA-N
comment: Compound 6b was designed to inhibit ferrous ion transport via the divalent metal transporter 1 (DMT1; SLC11A2) <Reference id=29881/>.
iupac name: [2-[2-(carbamimidoylsulfanylmethyl)-4-fluorophenyl]sulfanyl-5-nitrophenyl]methyl carbamimidothioate
xref: CHEMBL2078890
approved: f
ligand name: compound 6b [PMID: 22749870]
type: SyntheticOrganicLigand

compound 30 [PMID: 16455256]
in ch i key: JOFQERPJMGKMMX-QGZVFWFLSA-N
in ch i: InChI=1S/C26H28N4O4S/c1-15(2)13-30-25-22(23(32)28(3)26(30)34)21(24(33)29-11-9-17(31)14-29)20(35-25)12-16-8-10-27-19-7-5-4-6-18(16)19/h4-8,10,15,17,31H,9,11-14H2,1-3H3/t17-/m1/s1
comment: Compound 30 is an inhibitor of the monocarboxylate transporter MCT1 (SLC16A1) with favourable drug-like properties and in vitro antiinflammatory activity <Reference id=29880/>.
iupac name: 5-[(3R)-3-hydroxypyrrolidine-1-carbonyl]-3-methyl-1-(2-methylpropyl)-6-(quinolin-4-ylmethyl)thieno[3,2-e]pyrimidine-2,4-dione
xref: CHEMBL205742
approved: f
ligand name: compound 30 [PMID: 16455256]
type: SyntheticOrganicLigand

compound 30 [PMID: 15953724]
in ch i key: IYCJVTFMIQICDJ-UHFFFAOYSA-N
in ch i: InChI=1S/C34H31ClFNO2/c1-21-7-5-6-8-27(21)28-15-11-25(18-30(28)36)24-12-16-31-29(17-24)22(2)32(19-34(3,4)33(38)39)37(31)20-23-9-13-26(35)14-10-23/h5-18H,19-20H2,1-4H3,(H,38,39)
comment: Compound 30 was designed as an inhibitor of inducible microsomal prostaglandin E2 synthase (mPGES1; PTGES) <Reference id=29877/>.
iupac name: 3-[1-[(4-chlorophenyl)methyl]-5-[3-fluoro-4-(2-methylphenyl)phenyl]-3-methylindol-2-yl]-2,2-dimethylpropanoic acid
xref: CHEMBL180650
approved: f
ligand name: compound 30 [PMID: 15953724]
type: SyntheticOrganicLigand

(5Z)-1-(2-fluorophenyl)-2-sulfanylidene-5-(thiophen-2-ylmethylidene)-1,3-diazinane-4,6-dione
canonical SMILES: O=C1NC(=S)N(C(=O)C1=Cc1cccs1)c1ccccc1F
isomeric SMILES: O=C1NC(=S)N(C(=O)/C/1=C/c1cccs1)c1ccccc1F
in ch i key: MKKQUOFAFVQDCS-NTMALXAHSA-N
in ch i: InChI=1S/C15H9FN2O2S2/c16-11-5-1-2-6-12(11)18-14(20)10(13(19)17-15(18)21)8-9-4-3-7-22-9/h1-8H,(H,17,19,21)/b10-8-
comment: This compound is a small molecule, reversible inhibitor of the regulator of G-protein signaling 4 (RGS4) protein.
iupac name: (5Z)-1-(2-fluorophenyl)-2-sulfanylidene-5-(thiophen-2-ylmethylidene)-1,3-diazinane-4,6-dione
xref: CHEMBL1408705
approved: f
ligand name: (5Z)-1-(2-fluorophenyl)-2-sulfanylidene-5-(thiophen-2-ylmethylidene)-1,3-diazinane-4,6-dione
type: SyntheticOrganicLigand

compound 53 [PMID: 19631533]
in ch i key: HCCNBKFJYUWLEX-UHFFFAOYSA-N
in ch i: InChI=1S/C23H25N7O3/c1-3-9-33-10-8-30-20-11-18(16-4-5-21(32-2)27-12-16)26-15-19(20)29-22(23(30)31)28-14-17-13-24-6-7-25-17/h4-7,11-13,15H,3,8-10,14H2,1-2H3,(H,28,29)
comment: Compound 53 was developed as a drug-like inhibitor of phosphodiesterase 5 (PDE5) <Reference id=29876/>.
iupac name: 7-(6-methoxypyridin-3-yl)-1-(2-propoxyethyl)-3-(pyrazin-2-ylmethylamino)pyrido[3,4-b]pyrazin-2-one
xref: CHEMBL567470
approved: f
ligand name: compound 53 [PMID: 19631533]
type: SyntheticOrganicLigand

compound 1l [PMID: 16644217]
isomeric SMILES: CCCC/C=C/COC(=O)C1=C(C)NC(=O)NC1c1ccc(cc1)[N+](=O)[O-]
in ch i key: BEXZJJQVPWJPOA-VOTSOKGWSA-N
in ch i: InChI=1S/C19H23N3O5/c1-3-4-5-6-7-12-27-18(23)16-13(2)20-19(24)21-17(16)14-8-10-15(11-9-14)22(25)26/h6-11,17H,3-5,12H2,1-2H3,(H2,20,21,24)/b7-6+
comment: Compound 1l potently inhibits the fatty acid transport protein 4 (SLC27A4) <Reference id=17536/>.
iupac name: [(E)-hept-2-enyl] 6-methyl-4-(4-nitrophenyl)-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate
xref: CHEMBL209855
approved: f
ligand name: compound 1l [PMID: 16644217]
type: SyntheticOrganicLigand

compound 45 [PMID: 8709105]
in ch i key: PSLUFJFHTBIXMW-WYEYVKMPSA-N
in ch i: InChI=1S/C30H42N2O8/c1-8-27(5)17-21(35)30(37)28(6)20(34)12-14-26(3,4)23(28)22(24(38-18(2)33)29(30,7)40-27)39-25(36)32-16-13-19-11-9-10-15-31-19/h8-11,15,20,22-24,34,37H,1,12-14,16-17H2,2-7H3,(H,32,36)/t20-,22-,23-,24-,27-,28-,29+,30-/m0/s1
comment: Compound 45 is the highest affinity ligand identified in three series of forskolin analogues synthesised to assess SAR for adenylyl cyclase isoforms <Reference id=29874/>.
iupac name: [(3R,4aR,5S,6S,6aS,10S,10aR,10bS)-3-ethenyl-10,10b-dihydroxy-3,4a,7,7,10a-pentamethyl-1-oxo-6-(2-pyridin-2-ylethylcarbamoyloxy)-5,6,6a,8,9,10-hexahydro-2H-benzo[f]chromen-5-yl] acetate
xref: CHEMBL328689
approved: f
ligand name: compound 45 [PMID: 8709105]
type: SyntheticOrganicLigand

compound 13b [PMID: 19101153]
in ch i key: LSWVRWFSRJQEKB-SJORKVTESA-N
in ch i: InChI=1S/C19H15ClN2O4/c1-19(2)17(23)16(13-7-10(9-21)3-6-14(13)25-19)22-18(24)12-5-4-11(20)8-15(12)26-22/h3-8,16-17,23H,1-2H3/t16-,17+/m1/s1
comment: Compound 13b is one of a series of experimantal compounds tested as KATP channel openers <Reference id=29873/>, with the aim of discovering leads structures which could be developed in to drugs to treat urge urinary incontinence (overactive bladder). Functional KATP channels in the smooth muscle of the bladder are complexes of the sulfonylurea receptor 2 (SUR2; ABCC9) and the inwardly rectifying potassium channel subunit (Kir6.2; KCNJ11).
iupac name: (3S,4R)-4-(6-chloro-3-oxo-1,2-benzoxazol-2-yl)-3-hydroxy-2,2-dimethyl-3,4-dihydrochromene-6-carbonitrile
xref: CHEMBL473744
approved: f
ligand name: compound 13b [PMID: 19101153]
type: SyntheticOrganicLigand

naphthylvinylmethylpyridine
canonical SMILES: C[n+]1ccc(cc1)C=Cc1cccc2c1cccc2
isomeric SMILES: C[n+]1ccc(cc1)/C=C/c1cccc2c1cccc2
in ch i key: FJFKCRZPKGCGJE-MDZDMXLPSA-N
in ch i: InChI=1S/C18H16N/c1-19-13-11-15(12-14-19)9-10-17-7-4-6-16-5-2-3-8-18(16)17/h2-14H,1H3/q+1/b10-9+
comment: Compound 2 is one of a series of compounds investigated as inhibitors of choline O-acetyltransferase (CHAT, a.k.a. choline acetyltransferase) <Reference id=29872/>, in the search for compounds with the ability to provide protection against nerve agent poisoning.
iupac name: 1-methyl-4-[(E)-2-naphthalen-1-ylethenyl]pyridin-1-ium
xref: CHEMBL106212
synonym: compound 2 [PMID: 3351860]
synonym: (E)-4-(1-naphthylvinyl)pyridine methochloride
approved: f
ligand name: naphthylvinylmethylpyridine
type: SyntheticOrganicLigand

A1P
canonical SMILES: OC(=O)C(CCCn1ccnc1N)N
isomeric SMILES: OC(=O)[C@H](CCCn1ccnc1N)N
in ch i key: WGFGZNVQMGCHHV-LURJTMIESA-N
in ch i: InChI=1S/C8H14N4O2/c9-6(7(13)14)2-1-4-12-5-3-11-8(12)10/h3,5-6H,1-2,4,9H2,(H2,10,11)(H,13,14)/t6-/m0/s1
comment: A1P is reported as an inhibitor of human arginase 1 <Reference id=29871/>.
iupac name: (2S)-2-amino-5-(2-aminoimidazol-1-yl)pentanoic acid
xref: CHEMBL1099169
synonym: compound 10 [PMID: 20441173]
approved: f
ligand name: A1P
type: SyntheticOrganicLigand

compound 82 [PMID: 21332118]
in ch i key: YGBMCLDVRUGXOV-UHFFFAOYSA-N
comment: Compound 82 is reported as a pan inhibitor of type I PI3 kinases (PI3Kα/β/γ/δ), with dual activity as a mTOR inhibitor <Reference id=29870/>.
iupac name: N-[6-[6-chloro-5-[(4-fluorophenyl)sulfonylamino]pyridin-3-yl]-1,3-benzothiazol-2-yl]acetamide
xref: CHEMBL1615189
approved: f
ligand name: compound 82 [PMID: 21332118]
type: SyntheticOrganicLigand

ritonavir
in ch i key: NCDNCNXCDXHOMX-XGKFQTDJSA-N
in ch i: InChI=1S/C37H48N6O5S2/c1-24(2)33(42-36(46)43(5)20-29-22-49-35(40-29)25(3)4)34(45)39-28(16-26-12-8-6-9-13-26)18-32(44)31(17-27-14-10-7-11-15-27)41-37(47)48-21-30-19-38-23-50-30/h6-15,19,22-25,28,31-33,44H,16-18,20-21H2,1-5H3,(H,39,45)(H,41,47)(H,42,46)/t28-,31-,32-,33-/m0/s1
comment: Ritonavir is an orally bioavailable antiviral that is generally administered in combination with other anti-HIV or anti-HCV drugs.
iupac name: 1,3-thiazol-5-ylmethyl N-[(2S,3S,5S)-3-hydroxy-5-[[(2S)-3-methyl-2-[[methyl-[(2-propan-2-yl-1,3-thiazol-4-yl)methyl]carbamoyl]amino]butanoyl]amino]-1,6-di(phenyl)hexan-2-yl]carbamate
xref: CHEMBL163
synonym: ABT-538
synonym: ABT 538
synonym: Norvir®
synonym: ABBOTT-84538
synonym: A-84538
approved: t
ligand name: ritonavir
type: SyntheticOrganicLigand

apstatin
in ch i key: YVUUZAPYLPWFHE-HXFGRODQSA-N
in ch i: InChI=1S/C23H33N5O5/c1-14(20(25)30)26-21(31)17-9-5-11-27(17)22(32)18-10-6-12-28(18)23(33)19(29)16(24)13-15-7-3-2-4-8-15/h2-4,7-8,14,16-19,29H,5-6,9-13,24H2,1H3,(H2,25,30)(H,26,31)/t14-,16+,17-,18-,19-/m0/s1
comment: Apstatin is a tri-peptide-like inhibitor of membrane bound aminopeptidase P (mAPP; XPNPEP2) <Reference id=28821/>, which inhibits mAPP-induced degradation of bradykinin <Reference id=29867/>.
iupac name: (2S)-1-[(2S)-1-[(2S,3R)-3-amino-2-hydroxy-4-phenylbutanoyl]pyrrolidine-2-carbonyl]-N-[(2S)-1-amino-1-oxopropan-2-yl]pyrrolidine-2-carboxamide
xref: CHEMBL311875
approved: f
ligand name: apstatin
type: SyntheticOrganicLigand

estradiol disulfate
in ch i key: VPLAJGAMHNQZIY-ZBRFXRBCSA-N
in ch i: InChI=1S/C18H24O8S2/c1-18-9-8-14-13-5-3-12(25-27(19,20)21)10-11(13)2-4-15(14)16(18)6-7-17(18)26-28(22,23)24/h3,5,10,14-17H,2,4,6-9H2,1H3,(H,19,20,21)(H,22,23,24)/t14-,15-,16+,17+,18+/m1/s1
comment: <Ligand id=1013/> is the most potent mammalian estrogenic steroid. This is the sulphated form of that compound.
iupac name: [(8R,9S,13S,14S,17S)-13-methyl-3-sulfooxy-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl] hydrogen sulfate
xref: CHEMBL1162492
synonym: 17beta-estradiol-3,17-disulfate
synonym: estradiol-3,17-disulfate
approved: f
ligand name: estradiol disulfate
type: SyntheticOrganicLigand

compound 5k [PMID: 23528296]
in ch i key: ORQHHLPTMSGMQT-UHFFFAOYSA-N
in ch i: InChI=1S/C18H22FN5OS/c19-13-5-6-16(20-11-13)24-9-7-23(8-10-24)12-17(25)22-18-21-14-3-1-2-4-15(14)26-18/h5-6,11H,1-4,7-10,12H2,(H,21,22,25)
comment: Compound 5k is one of the most potent compounds reported in a series designed to identify fatty acid transport protein 1 (SLC27A1) inhibitors <Reference id=29864/>. Compound 5k also has favourable pharmacokinetic properties.
iupac name: 2-[4-(5-fluoropyridin-2-yl)piperazin-1-yl]-N-(4,5,6,7-tetrahydro-1,3-benzothiazol-2-yl)acetamide
xref: CHEMBL2377621
approved: f
ligand name: compound 5k [PMID: 23528296]
type: SyntheticOrganicLigand

2-monoacylglycerol
canonical SMILES: OCC(OC=O)CO
isomeric SMILES: OCC(OC=O)CO
in ch i key: LDVVTQMJQSCDMK-UHFFFAOYSA-N
in ch i: InChI=1S/C4H8O4/c5-1-4(2-6)8-3-7/h3-6H,1-2H2
iupac name: 1,3-dihydroxypropan-2-yl formate
synonym: 2-acylglycerol
synonym: 1-alkyl-2-acylglycerol
synonym: 2-monoglyceride
synonym: monoglyceride
approved: f
ligand name: 2-monoacylglycerol
type: NaturalProductLigand

azalanstat
in ch i key: VYNIUBZKEWJOJP-UNMCSNQZSA-N
comment: Azalanstat (as compound 1) is reported as a competitive inhibitor of mammalian lanosterol 14-α-demethylase (CYP51A1) <Reference id=29863/>.
iupac name: 4-[[(2S,4S)-2-[2-(4-chlorophenyl)ethyl]-2-(imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methylsulfanyl]aniline
xref: CHEMBL70611
synonym: compound 1 [PMID: 8340925]
synonym: RS-21607197
approved: f
ligand name: azalanstat
type: NaturalProductLigand

cefalotin
in ch i key: XIURVHNZVLADCM-IUODEOHRSA-N
in ch i: InChI=1S/C16H16N2O6S2/c1-8(19)24-6-9-7-26-15-12(14(21)18(15)13(9)16(22)23)17-11(20)5-10-3-2-4-25-10/h2-4,12,15H,5-7H2,1H3,(H,17,20)(H,22,23)/t12-,15-/m1/s1
comment: Cefalotin is a semisynthetic, first generation cephalosporin belonging to the β-lactam class of antibacterial compounds <Reference id=44149/>.
iupac name: (6R,7R)-3-(acetyloxymethyl)-8-oxo-7-[(2-thiophen-2-ylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
xref: CHEMBL617
synonym: cephalotin
synonym: cephalothin
synonym: Keflin®
approved: t
ligand name: cefalotin
type: SyntheticOrganicLigand

compound 13 [PMID: 17502136]
in ch i key: RZFRHJXGOFXNIG-UHFFFAOYSA-N
in ch i: InChI=1S/C21H14Cl4O4/c22-14-6-4-12(17(24)8-14)10-28-19-3-1-2-16(21(26)27)20(19)29-11-13-5-7-15(23)9-18(13)25/h1-9H,10-11H2,(H,26,27)
comment: Compound 13 is reported as a potent inhibitor of both muscle and adipocyte fatty acid binding proteins (FABP3 and FABP4 respectively) <Reference id=22696/>.
iupac name: 2,3-bis[(2,4-dichlorophenyl)methoxy]benzoic acid
xref: CHEMBL1908862
approved: f
ligand name: compound 13 [PMID: 17502136]
type: SyntheticOrganicLigand

FIPI
in ch i key: LHABRXRGDLASIH-UHFFFAOYSA-N
in ch i: InChI=1S/C23H24FN5O2/c24-16-5-6-18-15(13-16)14-20(26-18)22(30)25-9-12-28-10-7-17(8-11-28)29-21-4-2-1-3-19(21)27-23(29)31/h1-6,13-14,17,26H,7-12H2,(H,25,30)(H,27,31)
comment: FIPI is a phospholipase D1/D2 inhibitor <Reference id=29837/>. Suppresses membrane ruffling.
iupac name: 5-fluoro-N-[2-[4-(2-oxo-3H-benzimidazol-1-yl)piperidin-1-yl]ethyl]-1H-indole-2-carboxamide
xref: CHEMBL398567
synonym: compound 14 [PMID: 19136975]
approved: f
ligand name: FIPI
type: SyntheticOrganicLigand

compound 6ee [PMID: 22364528]
in ch i key: COBUMZLYZWRZDS-UHFFFAOYSA-N
in ch i: InChI=1S/C33H30N8O3/c1-22-3-2-15-34-28(22)20-39-17-13-33(14-18-39)31(43)40(32(44)41(33)29-19-30(42)36-21-35-29)26-10-8-24(9-11-26)23-4-6-25(7-5-23)27-12-16-37-38-27/h2-12,15-16,19,21H,13-14,17-18,20H2,1H3,(H,37,38)(H,35,36,42)
comment: Compound 6ee is reported from a SAR exploration to identify pan-hypoxia-Inducible factor prolyl hydroxylase 1-3 (HIF PHD1-3) inhibitors with drug-like properties as potential anti-anemia therapeutics <Reference id=29856/>.
iupac name: 8-[(3-methylpyridin-2-yl)methyl]-1-(4-oxo-1H-pyrimidin-6-yl)-3-[4-[4-(1H-pyrazol-5-yl)phenyl]phenyl]-1,3,8-triazaspiro[4.5]decane-2,4-dione
xref: CHEMBL2041169
approved: f
ligand name: compound 6ee [PMID: 22364528]
type: SyntheticOrganicLigand

compound 7p [PMID: 7861416]
in ch i key: HCFZUTSDEMKXQB-UHFFFAOYSA-N
in ch i: InChI=1S/C24H28BrNO5/c1-24(2,31-20-12-10-19(25)11-13-20)23-29-16-18(7-4-3-5-9-21(27)28)22(30-23)17-8-6-14-26-15-17/h3-4,6,8,10-15,18,22-23H,5,7,9,16H2,1-2H3,(H,27,28)
comment: Compound 7p was developed as one in series of compounds with the aim of identifying dual-acting thromboxane receptor antagonist/synthase inhibitors <Reference id=29855/>. In fact compound 7p shows selectivity for prostaglandin I2 synthase (PTGIS, CYP8A1) over thromboxane synthase (CYP5A1).
iupac name: (Z)-6-[2-[2-(4-bromophenoxy)propan-2-yl]-4-pyridin-3-yl-1,3-dioxan-5-yl]hex-4-enoic acid
xref: CHEMBL159859
approved: f
ligand name: compound 7p [PMID: 7861416]
type: SyntheticOrganicLigand

compound 1b [PMID: 9871762]
in ch i key: NEIYCJCCYGTVNA-VQHVLOKHSA-N
in ch i: InChI=1S/C25H34N2O3S2/c1-6-27(16-9-7-8-15-25(2,3)4)21-22-12-10-13-23(20-22)30-18-17-26(5)32(28,29)24-14-11-19-31-24/h7,9-14,19-20H,6,16-18,21H2,1-5H3/b9-7+
comment: Compound 1b is reported to inhibit the cholesterol biosynthesic activity of squalene epoxidase (SQLE) in human HepG2 <Reference id=29854/>.
iupac name: N-[2-[3-[[[(E)-6,6-dimethylhept-2-en-4-ynyl]-ethylamino]methyl]phenoxy]ethyl]-N-methylthiophene-2-sulfonamide
xref: CHEMBL281025
approved: f
ligand name: compound 1b [PMID: 9871762]
type: SyntheticOrganicLigand

SAR260301
in ch i key: UAXHPOBBKRWJGA-ZDUSSCGKSA-N
in ch i: InChI=1S/C19H22N4O3/c1-13-10-14-4-2-3-5-15(14)23(13)19(25)11-16-20-17(12-18(24)21-16)22-6-8-26-9-7-22/h2-5,12-13H,6-11H2,1H3,(H,20,21,24)/t13-/m0/s1
comment: SAR260301 (compound 28 [PMID: 24387221]) was reported in a discovery effort to optimize pyrimidone indoline amide inhibitors of PI3Kβ <Reference id=29853/>. It is an orally bioavailable compound that is selective for PI3Kβ over other PI3 kinases.
iupac name: 2-[2-[(2S)-2-methyl-2,3-dihydroindol-1-yl]-2-oxoethyl]-6-morpholin-4-yl-1H-pyrimidin-4-one
xref: CHEMBL3112866
synonym: compound 28 [PMID: 24387221]
synonym: SAR-260301
synonym: SAR 260301
approved: f
ligand name: SAR260301
type: SyntheticOrganicLigand

A1120
in ch i key: MEAQCLPMSVEOQF-UHFFFAOYSA-N
in ch i: InChI=1S/C20H19F3N2O3/c21-20(22,23)16-7-3-1-5-14(16)13-9-11-25(12-10-13)19(28)24-17-8-4-2-6-15(17)18(26)27/h1-8,13H,9-12H2,(H,24,28)(H,26,27)
comment: A1120 is reported as a potent non-retinoid inhibitor of plasma retinol-binding protein RBP4 <Reference id=29850/>.
iupac name: 2-[[4-[2-(trifluoromethyl)phenyl]piperidine-1-carbonyl]amino]benzoic acid
xref: CHEMBL1230001
synonym: A 1120
synonym: compound 33 [PMID: 24835984]
approved: f
ligand name: A1120
type: SyntheticOrganicLigand

compound 33 [Toda et al., 2013]
in ch i key: ATOKVTDUHKZLMB-UHFFFAOYSA-N
in ch i: InChI=1S/C22H30N8O2/c1-4-32-14-19-18(21(31)24-12-17-11-23-15-28(17)3)13-26-30(19)22-25-10-16(2)20(27-22)29-8-6-5-7-9-29/h10-11,13,15H,4-9,12,14H2,1-3H3,(H,24,31)
comment: Compound 33 is reported as a GPR142 agonist and provides evidence to support the hypothesis that GPR142 agonists act as insulin secretagogues, which could eventually lead to the discovery of novel treatments for type 2 diabetes mellitus <Reference id=28265/>.
iupac name: 5-(ethoxymethyl)-N-[(3-methylimidazol-4-yl)methyl]-1-(5-methyl-4-piperidin-1-ylpyrimidin-2-yl)pyrazole-4-carboxamide
xref: CHEMBL2409007
approved: f
ligand name: compound 33 [Toda et al., 2013]
type: SyntheticOrganicLigand

compound 5 [PMID: 21838328]
in ch i key: GJYCFJGZPVJOKR-UHFFFAOYSA-N
in ch i: InChI=1S/C26H27N3O2/c1-4-31-25(30)26(2,3)24(29-16-15-27-18-29)20-10-12-22(13-11-20)28-23-14-9-19-7-5-6-8-21(19)17-23/h5-18,24,28H,4H2,1-3H3
comment: Compound 5 inhibits the activity of the cytochrome P450 enzyme CYP26A1, with selectivity against the other CYPs tested <Reference id=29848/>.
iupac name: ethyl 3-imidazol-1-yl-2,2-dimethyl-3-[4-(naphthalen-2-ylamino)phenyl]propanoate
xref: CHEMBL1831083
approved: f
ligand name: compound 5 [PMID: 21838328]
type: SyntheticOrganicLigand

chrysin
canonical SMILES: Oc1cc(O)c2c(c1)oc(cc2=O)c1ccccc1
isomeric SMILES: Oc1cc(O)c2c(c1)oc(cc2=O)c1ccccc1
in ch i key: RTIXKCRFFJGDFG-UHFFFAOYSA-N
in ch i: InChI=1S/C15H10O4/c16-10-6-11(17)15-12(18)8-13(19-14(15)7-10)9-4-2-1-3-5-9/h1-8,16-17H
comment: Chrysin is a dietary flavinoid. It is reported to inhibit the EROD (7-ethoxyresorufin-O-deethylase) activity of the extrahepatic cytochrome P450 enzymes CYP1A1 and CYP1B1 <Reference id=29847/>. The compound also has antibacterial activity against Gram-negative Helicobacter pylori and is reported to inhibit H. pylori HsrA (homeostatic stress regulator) <Reference id=39723/>.
iupac name: 5,7-dihydroxy-2-phenylchromen-4-one
xref: CHEMBL117
synonym: NSC-407436
approved: f
ligand name: chrysin
type: NaturalProductLigand

HM50316
in ch i key: HOACFVYJBHHSBC-UHFFFAOYSA-N
comment: HM50316 is a potent and selective inhibitor of human adipocyte fatty acid-binding protein <Reference id=29846/>.
iupac name: 2-[3-[2-[1-(4-chlorophenyl)-5-thiophen-2-ylpyrazol-3-yl]phenyl]phenoxy]-2-methylpropanoic acid
xref: CHEMBL1782969
synonym: compound 5g [PMID: 21481589]
synonym: HM 50316
approved: f
ligand name: HM50316
type: SyntheticOrganicLigand

compound 12e [PMID: 18605714]
in ch i key: YLSSVFGTKZXLPA-UHFFFAOYSA-N
in ch i: InChI=1S/C25H22N2O5/c1-2-18-21(24(30)25(26)31)22-19(32-14-20(28)29)12-16-10-6-7-11-17(16)23(22)27(18)13-15-8-4-3-5-9-15/h3-12H,2,13-14H2,1H3,(H2,26,31)(H,28,29)
comment: Compound 12e is one of the structures tested as an inhibitor of mammalian secreted phospholipases A2 <Reference id=29841/>.
iupac name: 2-[2-ethyl-3-oxamoyl-1-(phenylmethyl)benzo[g]indol-4-yl]oxyacetic acid
xref: CHEMBL515637
approved: f
ligand name: compound 12e [PMID: 18605714]
type: SyntheticOrganicLigand

compound 13e [PMID: 16759857]
in ch i key: MKLXYDUSWQDVEW-UHFFFAOYSA-N
in ch i: InChI=1S/C23H25N5O5S/c1-16-24-21(32-26-16)23(22-25-17(2)27-33-22,14-6-9-18-7-4-3-5-8-18)15-19-10-12-20(13-11-19)28-34(29,30)31/h3-5,7-8,10-13,28H,6,9,14-15H2,1-2H3,(H,29,30,31)
comment: The development of compound 13e is reported in <Reference id=29842/>. This compound inhibits the endothelially expressed receptor tyrosine phosphatase HPTPβ (PTPRB).
iupac name: [4-[2,2-bis(3-methyl-1,2,4-oxadiazol-5-yl)-5-phenylpentyl]phenyl]sulfamic acid
xref: CHEMBL1185062
approved: f
ligand name: compound 13e [PMID: 16759857]
type: SyntheticOrganicLigand

compound 7 [PMID: 21334791]
canonical SMILES: Oc1ccc(c(c1)O)CCc1ccc(cc1O)O
isomeric SMILES: Oc1ccc(c(c1)O)CCc1ccc(cc1O)O
in ch i key: WKIFTWPZTZUMRN-UHFFFAOYSA-N
in ch i: InChI=1S/C14H14O4/c15-11-5-3-9(13(17)7-11)1-2-10-4-6-12(16)8-14(10)18/h3-8,15-18H,1-2H2
comment: Compound 7 is reported as a tyrosinase inhibitor <Reference id=29840/>.
iupac name: 4-[2-(2,4-dihydroxyphenyl)ethyl]benzene-1,3-diol
xref: CHEMBL499124
approved: f
ligand name: compound 7 [PMID: 21334791]
type: SyntheticOrganicLigand

SGI-1776
in ch i key: MHXGEROHKGDZGO-UHFFFAOYSA-N
in ch i: InChI=1S/C20H22F3N5O/c1-27-9-7-14(8-10-27)12-24-18-5-6-19-25-13-17(28(19)26-18)15-3-2-4-16(11-15)29-20(21,22)23/h2-6,11,13-14H,7-10,12H2,1H3,(H,24,26)
comment: SGI-1776 is a pan PIM kinase inhibitor that was developed for potential antineoplastic activity <Reference id=29839/>.
iupac name: N-[(1-methylpiperidin-4-yl)methyl]-3-[3-(trifluoromethoxy)phenyl]imidazo[2,1-f]pyridazin-6-amine
xref: CHEMBL1952329
synonym: SGI 1776
synonym: SGI1776
approved: f
ligand name: SGI-1776
type: SyntheticOrganicLigand

compound 26 [PMID: 21733693]
in ch i key: KJUCPVIVNLPLEE-UHFFFAOYSA-N
comment: Compound 26 was developed in a study to discover novel inhibitors of the constitutively active V600E mutant BRAF kinase <Reference id=29838/>.
iupac name: 2,6-difluoro-N-[2-fluoro-5-[5-[2-[(6-morpholin-4-ylpyridin-3-yl)amino]pyrimidin-4-yl]-2-propan-2-yl-1,3-thiazol-4-yl]phenyl]benzenesulfonamide
xref: CHEMBL1808264
synonym: Example 23 [WO2010104899A1]
approved: f
ligand name: compound 26 [PMID: 21733693]
type: SyntheticOrganicLigand

compound 69 [PMID: 19136975]
in ch i key: DRIMIUYGTDAQOX-KRWDZBQOSA-N
in ch i: InChI=1S/C26H27ClN4O2/c1-17(28-25(32)20-7-6-18-4-2-3-5-19(18)14-20)16-30-12-10-22(11-13-30)31-24-9-8-21(27)15-23(24)29-26(31)33/h2-9,14-15,17,22H,10-13,16H2,1H3,(H,28,32)(H,29,33)/t17-/m0/s1
comment: Compound 69 is a phospholipase D inhibitor with approximately 20-fold selectivity for PLD1 over PLD2 <Reference id=29837/>.
iupac name: N-[(2S)-1-[4-(5-chloro-2-oxo-3H-benzimidazol-1-yl)piperidin-1-yl]propan-2-yl]naphthalene-2-carboxamide
xref: CHEMBL492572
approved: f
ligand name: compound 69 [PMID: 19136975]
type: SyntheticOrganicLigand

uric acid
canonical SMILES: O=c1[nH]c2c([nH]1)[nH]c(=O)[nH]c2=O
isomeric SMILES: O=c1[nH]c2c([nH]1)[nH]c(=O)[nH]c2=O
in ch i key: LEHOTFFKMJEONL-UHFFFAOYSA-N
in ch i: InChI=1S/C5H4N4O3/c10-3-1-2(7-4(11)6-1)8-5(12)9-3/h(H4,6,7,8,9,10,11,12)
iupac name: 2,3,6,7,8,9-hexahydro-1H-purine-2,6,8-trione
xref: CHEMBL792
synonym: urate
approved: f
ligand name: uric acid
type: MetaboliteLigand

compound 8e [PMID: 23044371]
in ch i key: CYKYMBAFNWGXGM-UHFFFAOYSA-N
in ch i: InChI=1S/C29H22ClNO5/c30-24-13-9-21(10-14-24)27(32)19-36-29(34)22-11-15-25(16-12-22)31-28(33)23-7-4-8-26(17-23)35-18-20-5-2-1-3-6-20/h1-17H,18-19H2,(H,31,33)
comment: Compound 8e inhibits sentrin/SUMO-specific peptidase 1 (SENP1) <Reference id=29836/>.
iupac name: [2-(4-chlorophenyl)-2-oxoethyl] 4-[(3-phenylmethoxybenzoyl)amino]benzoate
xref: CHEMBL2159857
approved: f
ligand name: compound 8e [PMID: 23044371]
type: SyntheticOrganicLigand

compound 10h [PMID: 20832306]
in ch i key: WNFAQVLTRONMFD-UHFFFAOYSA-N
comment: Compound 10h is a potent inhibitor of malonyl-CoA decarboxylase <Reference id=29835/>. Such compounds are predicted to have anti-obesity and anti-diabetic activities.
iupac name: 3-[4-carbamoyl-1-[5-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)-1,3-thiazol-2-yl]piperidin-4-yl]benzoic acid
xref: CHEMBL1258253
approved: f
ligand name: compound 10h [PMID: 20832306]
type: SyntheticOrganicLigand

compound 17 [PMID: 23570514]
in ch i key: XZEVSGANERUOOE-UHFFFAOYSA-N
in ch i: InChI=1S/C24H29N5O4S2/c1-24(2,3)33-23(32)17-5-4-16(34-17)22(31)26-9-6-14-7-10-29(11-8-14)21-19-15(27-13-28-21)12-18(35-19)20(25)30/h4-5,12-14H,6-11H2,1-3H3,(H2,25,30)(H,26,31)
comment: Compound 17 is one of a number of pan SIRT1/2/3 inhibitors identified in <Reference id=29832/>.
iupac name: tert-butyl 5-[2-[1-(6-carbamoylthieno[3,2-d]pyrimidin-4-yl)piperidin-4-yl]ethylcarbamoyl]thiophene-2-carboxylate
xref: CHEMBL2332041
approved: f
ligand name: compound 17 [PMID: 23570514]
type: SyntheticOrganicLigand

compound 51 [Crosignani et al., 2011]
in ch i key: XQIZEBWLPMOVGN-UHFFFAOYSA-N
in ch i: InChI=1S/C18H15F4N5O2/c1-2-16(28)27(10-11-3-5-15(6-4-11)29-18(20,21)22)14-8-12(7-13(19)9-14)17-23-25-26-24-17/h3-9H,2,10H2,1H3,(H,23,24,25,26)
comment: Compound 51 was tested in a study to identify DP2 prostanoid receptor antagonists <Reference id=29831/>. The inhibitory action of the compound on cytochrome P450 enzymes was tested as a predictor of metabolic stability.
xref: CHEMBL2036213
approved: f
ligand name: compound 51 [Crosignani et al., 2011]
type: SyntheticOrganicLigand

PAK-104P
in ch i key: PFKHLXIJSNUZDT-KAYWLYCHSA-N
in ch i: InChI=1S/C38H43N4O7P/c1-26-24-27(2)49-50(46,48-26)37-29(4)39-28(3)34(35(37)32-16-11-17-33(25-32)42(44)45)38(43)47-23-22-40-18-20-41(21-19-40)36(30-12-7-5-8-13-30)31-14-9-6-10-15-31/h5-17,25-27,36H,18-24H2,1-4H3/t26-,27-/m1/s1
comment: PAK-104P is reported to inhibit the activity of the canalicular multispecific organic anion transporter 1 (cMOAT, ABCC2) <Reference id=29830/>.
iupac name: 2-[4-[di(phenyl)methyl]piperazin-1-yl]ethyl 5-[(4R,6R)-4,6-dimethyl-2-oxo-1,3-dioxa-2$l^{5}-phosphacyclohex-2-yl]-2,6-dimethyl-4-(3-nitrophenyl)pyridine-3-carboxylate
xref: CHEMBL2074650
synonym: PAK104P
approved: f
ligand name: PAK-104P
type: SyntheticOrganicLigand

LP-471756
canonical SMILES: Cc1ccccc1NS(=O)(=O)c1ccc(cc1)C1CCCCC1
isomeric SMILES: Cc1ccccc1NS(=O)(=O)c1ccc(cc1)C1CCCCC1
in ch i key: STLMNZVBCJVQOZ-UHFFFAOYSA-N
in ch i: InChI=1S/C19H23NO2S/c1-15-7-5-6-10-19(15)20-23(21,22)18-13-11-17(12-14-18)16-8-3-2-4-9-16/h5-7,10-14,16,20H,2-4,8-9H2,1H3
comment: LP-471756 is reported as an antagonist of GPR139 <Reference id=29828/>. LP-471756 and the GPR139 agonist <Ligand id=8773/> are useful tool compounds for further investigation of GPR139 function.
iupac name: 4-cyclohexyl-N-(2-methylphenyl)benzenesulfonamide
approved: f
ligand name: LP-471756
type: SyntheticOrganicLigand

LP-360924
in ch i key: OIRCJRUZRVLDFA-UHFFFAOYSA-N
in ch i: InChI=1S/C26H30N10O3S/c1-38-17-7-12-27-22-31-23(33-25(32-22)39-2)34-26-30-19(18-8-4-3-5-9-18)20(40-26)21(37)35-13-15-36(16-14-35)24-28-10-6-11-29-24/h3-6,8-11H,7,12-17H2,1-2H3,(H2,27,30,31,32,33,34)
comment: LP-360924 is reported as a surrogate agonist of GPR139 <Reference id=29828/>. LP-360924 and the GPR139 antagonist <Ligand id=8774/> are useful tool compounds for further investigation of GPR139 function.
iupac name: 6-methoxy-N2-(3-methoxypropyl)-N4-{4-phenyl-5-[4-(pyrimidin-2-yl)piperazine-1-carbonyl]-1,3-thiazol-2-yl}-1,3,5-triazine-2,4-diamine
approved: f
ligand name: LP-360924
type: SyntheticOrganicLigand

Dup-714
in ch i key: FXFYPTZERULUBS-SQNIBIBYSA-N
in ch i: InChI=1S/C21H33BN6O5/c1-14(29)26-16(13-15-7-3-2-4-8-15)20(31)28-12-6-9-17(28)19(30)27-18(22(32)33)10-5-11-25-21(23)24/h2-4,7-8,16-18,32-33H,5-6,9-13H2,1H3,(H,26,29)(H,27,30)(H4,23,24,25)/t16-,17+,18+/m1/s1
comment: Dup-714 is a small molecule thrombin inhibitor and as such is an antithrombotic agent <Reference id=29739/>. Galemmo et al. (1996) describe the development of novel antithrombotic compounds based on this structure <Reference id=29739/>.
iupac name: [(1R)-1-[[(2S)-1-[(2R)-2-acetamido-3-phenylpropanoyl]pyrrolidine-2-carbonyl]amino]-4-(diaminomethylideneamino)butyl]boronic acid
xref: CHEMBL290376
synonym: Dup 714
synonym: acetylphenylalanyl-prolyl-boroarginine
approved: f
ligand name: Dup-714
type: SyntheticOrganicLigand

L-NNA
canonical SMILES: [O-][N+](=O)NC(=NCCCC(C(=O)O)N)N
isomeric SMILES: [O-][N+](=O)NC(=NCCC[C@@H](C(=O)O)N)N
in ch i key: MRAUNPAHJZDYCK-BYPYZUCNSA-N
in ch i: InChI=1S/C6H13N5O4/c7-4(5(12)13)2-1-3-9-6(8)10-11(14)15/h4H,1-3,7H2,(H,12,13)(H3,8,9,10)/t4-/m0/s1
comment: L-NNA is an arginine analogue used as a biochemical tool in the study of nitric oxide and its biological effects. L-NNA inhibits the endothelial and neuronal isoforms of nitric oxide synthase (NOS), eNOS and nNOS respectively more potently than the inducible iNOS <Reference id=29738/>. Selective nNOS inhibitors are being pursued for their potential to treat neurological disorders caused by excessive production of nitric oxide.
xref: CHEMBL227744
synonym: nitroarginine
synonym: compound 2 [PMID: 9667974]
approved: f
ligand name: L-NNA
type: SyntheticOrganicLigand

Nrf2 peptide [PMID: 23647822]
in ch i key: LUWNQRCIIOOCLS-ITDBXDHNSA-N
comment: This Nrf2 peptide displaces the longer labeled Nrf2 mimetic peptide NH2-LQLDEETGEFLPIQGK(MR121)-OH from the central cavity of the Kelch-DC domain at the C-terminus of Keap1 (Kelch-like ECH-associated protein 1; KEAP1) <Reference id=29826/>. This article by Marcotte et al. (2013) also describes small molecule inhibitors of the Nrf2-Keap1 interaction e.g. Cpd16 (PubChem CID 1073725) binds Keap1 Kelch-DC with an IC50 of 2.7 µM <Reference id=29826/>.
xref: CHEMBL2402205
approved: f
ligand name: Nrf2 peptide [PMID: 23647822]
type: PeptideLigand

compound 57 [PMID: 16610804]
in ch i key: NXDZVUAKVFVDSL-UHFFFAOYSA-N
in ch i: InChI=1S/C30H37NO7/c1-3-4-5-6-7-8-9-10-17-37-24-12-14-25(15-13-24)38-21-23(32)19-31-20-27(30(35)36-2)26-18-22(29(33)34)11-16-28(26)31/h11-16,18,20H,3-10,17,19,21H2,1-2H3,(H,33,34)
comment: Compound 57 inhibits human cytosolic phospholipase A2α (PLA2G4A) <Reference id=29825/>.
iupac name: 1-[3-(4-decoxyphenoxy)-2-oxopropyl]-3-methoxycarbonylindole-5-carboxylic acid
xref: CHEMBL443834
approved: f
ligand name: compound 57 [PMID: 16610804]
type: SyntheticOrganicLigand

illudalic acid
canonical SMILES: O=Cc1c(O)c2CC(Cc2c2c1CC(O)OC2=O)(C)C
isomeric SMILES: O=Cc1c(O)c2CC(Cc2c2c1CC(O)OC2=O)(C)C
in ch i key: BDEDPKFUFGCVCJ-UHFFFAOYSA-N
in ch i: InChI=1S/C15H16O5/c1-15(2)4-8-9(5-15)13(18)10(6-16)7-3-11(17)20-14(19)12(7)8/h6,11,17-18H,3-5H2,1-2H3
comment: Illudalic acid selectively inhibits protein tyrosine phosphatase RTP Type F (LAR; PTPRF) <Reference id=29823/>.
iupac name: 3,6-dihydroxy-8,8-dimethyl-1-oxo-3,4,7,9-tetrahydrocyclopenta[h]isochromene-5-carbaldehyde
xref: CHEMBL506661
approved: f
ligand name: illudalic acid
type: SyntheticOrganicLigand

2-(2-thiazolyl)ethanamine
canonical SMILES: NCCc1nccs1
isomeric SMILES: NCCc1nccs1
in ch i key: TWZOYAWHWDRMEZ-UHFFFAOYSA-N
in ch i: InChI=1S/C5H8N2S/c6-2-1-5-7-3-4-8-5/h3-4H,1-2,6H2
iupac name: 2-(1,3-thiazol-2-yl)ethanamine
xref: CHEMBL25414
synonym: 2-(2-aminoethyl)thiazole
synonym: 2-thiazoleethanamine
synonym: 2-thiazolylethylamine
approved: f
ligand name: 2-(2-thiazolyl)ethanamine
type: SyntheticOrganicLigand

compound 38 [PMID: 20817473]
in ch i key: ORWIYCURPDKSBI-XMMPIXPASA-N
in ch i: InChI=1S/C29H32N6O3S/c36-28(21-8-10-22(11-9-21)35-14-16-38-17-15-35)31-27-26-23(32-33-27)18-25(39-26)29(37)30-24(19-34-12-4-5-13-34)20-6-2-1-3-7-20/h1-3,6-11,18,24H,4-5,12-17,19H2,(H,30,37)(H2,31,32,33,36)/t24-/m1/s1
comment: Compound 38 was developed as an Aurora kinase inhibitor and was investigated for its antitumour activity <Reference id=29820/>.
iupac name: 3-[(4-morpholin-4-ylbenzoyl)amino]-N-[(1S)-1-phenyl-2-pyrrolidin-1-ylethyl]-1H-thieno[5,4-d]pyrazole-5-carboxamide
xref: CHEMBL1258913
approved: f
ligand name: compound 38 [PMID: 20817473]
type: SyntheticOrganicLigand

FITM
in ch i key: WIVGIKIKQHUFOD-UHFFFAOYSA-N
in ch i: InChI=1S/C18H18FN5OS/c1-11(2)22-16-8-14(20-10-21-16)15-9-26-18(23-15)24(3)17(25)12-4-6-13(19)7-5-12/h4-11H,1-3H3,(H,20,21,22)
comment: This is the unlabeled version of <Ligand id=6213/>.
iupac name: 4-fluoro-N-methyl-N-[4-[6-(propan-2-ylamino)pyrimidin-4-yl]-1,3-thiazol-2-yl]benzamide
xref: CHEMBL566581
synonym: compound 5
approved: f
ligand name: FITM
type: SyntheticOrganicLigand

JNJ-63533054
canonical SMILES: O=C(NC(c1ccccc1)C)CNC(=O)c1cccc(c1)Cl
in ch i key: MWDVCHRYCKXEBY-LBPRGKRZSA-N
in ch i: InChI=1S/C17H17ClN2O2/c1-12(13-6-3-2-4-7-13)20-16(21)11-19-17(22)14-8-5-9-15(18)10-14/h2-10,12H,11H2,1H3,(H,19,22)(H,20,21)/t12-/m0/s1
comment: JNJ-63533054 is a small molecule agonist of GPR139 <Reference id=29817/><Reference id=37464/>. It is orally bioavailable and can cross the blood-brain barrier <Reference id=37463/>. It is a surrogate ligand that can be used to examine GPR139 function in the absence of a validated endogenous ligand. Both PubChem (CID 4879329) and ChEMBL (CHEMBL1509813) record this compound with no specified stereochemistry. Patent WO2014152917 A2 describes the search for physiological ligands for GPR139 <Reference id=29818/>.
iupac name: 3-chloro-N-[2-oxo-2-[[(1S)-1-phenylethyl]amino]ethyl]benzamide
xref: CHEMBL3633720
synonym: compound 7c [PMID: 26396690]
synonym: JNJ63533054
approved: f
ligand name: JNJ-63533054
type: SyntheticOrganicLigand

ML337
canonical SMILES: COc1ccc(cc1)C#Cc1ccc(c(c1)F)C(=O)N1CCCC(C1)O
isomeric SMILES: COc1ccc(cc1)C#Cc1ccc(c(c1)F)C(=O)N1CCC[C@H](C1)O
in ch i key: QBCRLDPMQHPGIM-QGZVFWFLSA-N
in ch i: InChI=1S/C21H20FNO3/c1-26-18-9-6-15(7-10-18)4-5-16-8-11-19(20(22)13-16)21(25)23-12-2-3-17(24)14-23/h6-11,13,17,24H,2-3,12,14H2,1H3/t17-/m1/s1
comment: ML337 is reported as a selective, brain penetrant, negative allosteric modulator of the metabotropic glutamate receptor mGlu3 <Reference id=29816/>.
iupac name: [2-fluoro-4-[2-(4-methoxyphenyl)ethynyl]phenyl]-[(3R)-3-hydroxypiperidin-1-yl]methanone
xref: CHEMBL2385886
synonym: ML 337
synonym: ML-337
approved: f
ligand name: ML337
type: SyntheticOrganicLigand

compound 28xvii [PMID: 8809154]
in ch i key: LNIJDTKDAASOIT-UHFFFAOYSA-N
in ch i: InChI=1S/C28H26N2O5/c1-2-21-22(16-20-12-7-6-11-19(20)15-18-9-4-3-5-10-18)30-14-8-13-23(35-17-24(31)32)26(30)25(21)27(33)28(29)34/h3-14H,2,15-17H2,1H3,(H2,29,34)(H,31,32)
comment: compound 28xvii is reported in <Reference id=29757/> as an inhibitor of secretory phospholopase A2 (sPLA2).
iupac name: 2-[2-ethyl-1-oxamoyl-3-[[2-(phenylmethyl)phenyl]methyl]indolizin-8-yl]oxyacetic acid
xref: CHEMBL331755
approved: f
ligand name: compound 28xvii [PMID: 8809154]
type: SyntheticOrganicLigand

compound 8 [PMID: 17480064]
canonical SMILES: O=C1NCCc2c1cc([nH]2)c1ccncc1
isomeric SMILES: O=C1NCCc2c1cc([nH]2)c1ccncc1
in ch i key: DKXHSOUZPMHNIZ-UHFFFAOYSA-N
in ch i: InChI=1S/C12H11N3O/c16-12-9-7-11(8-1-4-13-5-2-8)15-10(9)3-6-14-12/h1-2,4-5,7,15H,3,6H2,(H,14,16)
comment: Compound 8 is reported in <Reference id=26977/> as an inhibitor of mitogen-activated protein kinase-activated protein kinase 2 (MK-2; MAPKAPK2). Montagnoli et al. (2008) report the antitumour activity of this compound <Reference id=29752/>.
iupac name: 2-pyridin-4-yl-1,5,6,7-tetrahydropyrrolo[3,2-c]pyridin-4-one
xref: CHEMBL225519
synonym: PHA-767491
approved: f
ligand name: compound 8 [PMID: 17480064]
type: SyntheticOrganicLigand

WP814
in ch i key: LZWDZFWNTFSAGM-PGODJVSRSA-N
in ch i: InChI=1S/C31H33N3O14S/c1-48-17-4-2-3-12-22(17)28(43)24-23(25(12)40)26(41)13-7-31(47,8-16(35)21(13)27(24)42)18(36)11-49-10-15(29(44)33-9-20(38)39)34-19(37)6-5-14(32)30(45)46/h2-4,14-16,35,41-42,47H,5-11,32H2,1H3,(H,33,44)(H,34,37)(H,38,39)(H,45,46)/t14-,15-,16-,31-/m0/s1
comment: WP814 is <Ligand id=7069/> with the cysteinyl moiety of reduced glutathione (GSH) linked at the C-14 position <Reference id=29744/>. WP814 potently inhibits leukotriene C4 transport via the human multidrug resistance-associated protein 1 (ABCC1) in vitro.
iupac name: (2S)-2-amino-5-[[(2R)-1-(carboxymethylamino)-1-oxo-3-[2-oxo-2-[(2S,4S)-2,4,5,12-tetrahydroxy-7-methoxy-6,11-dioxo-3,4-dihydro-1H-tetracen-2-yl]ethyl]sulfanylpropan-2-yl]amino]-5-oxopentanoic acid
xref: CHEMBL2074989
approved: f
ligand name: WP814
type: SyntheticOrganicLigand

compound 44 [PMID: 19748780]
in ch i key: PYRKKGOKRMZEIT-UHFFFAOYSA-N
in ch i: InChI=1S/C32H27FN4O2/c1-32(2,38)15-19-5-7-24-26(11-19)27-14-23(39-10-9-18-3-4-18)6-8-25(27)30-29(24)36-31(37-30)28-20(16-34)12-22(33)13-21(28)17-35/h5-8,11-14,18,38H,3-4,9-10,15H2,1-2H3,(H,36,37)
comment: Compound 44 is one of the lead discovery compounds reported as potent inhibitors of prostaglandin E synthase (mPGES1, PTGES) <Reference id=29740/>.
iupac name: 2-[6-(2-cyclopropylethoxy)-9-(2-hydroxy-2-methylpropyl)-1H-phenanthro[9,10-d]imidazol-2-yl]-5-fluorobenzene-1,3-dicarbonitrile
xref: CHEMBL565406
approved: f
ligand name: compound 44 [PMID: 19748780]
type: SyntheticOrganicLigand

compound 19 [PMID: 22142545]
in ch i key: UBGXXNXAPLUDQK-UHFFFAOYSA-N
in ch i: InChI=1S/C18H22N4O2/c1-11-8-13(23-3)9-14-15(10-22-4-6-24-7-5-22)16-12(2)20-21-18(16)19-17(11)14/h8-9H,4-7,10H2,1-3H3,(H,19,20,21)
comment: Compound 19 is one of the most potent phosphodiesterase 10A inhibitors developed in a SAR study to identify PDE10 inhibitors as potential schizophrenia pharmaceuticals <Reference id=29737/>
iupac name: 4-[(6-methoxy-3,8-dimethyl-2H-pyrazolo[3,4-b]quinolin-4-yl)methyl]morpholine
xref: CHEMBL1939914
approved: f
ligand name: compound 19 [PMID: 22142545]
type: SyntheticOrganicLigand

compound 27 [PMID: 22142545]
in ch i key: IPHACPSYWWYGQN-UHFFFAOYSA-N
in ch i: InChI=1S/C19H24N4O2/c1-12-9-14(24-3)10-15-16(11-23-5-4-7-25-8-6-23)17-13(2)21-22-19(17)20-18(12)15/h9-10H,4-8,11H2,1-3H3,(H,20,21,22)
comment: Compound 27 was developed in a SAR study to identify PDE10 inhibitors as potential schizophrenia pharmaceuticals <Reference id=29737/>. This was the lead compound selected for further in vivo studies.
iupac name: 4-[(6-methoxy-3,8-dimethyl-2H-pyrazolo[3,4-b]quinolin-4-yl)methyl]-1,4-oxazepane
xref: CHEMBL1940053
synonym: SCH-1518291
approved: f
ligand name: compound 27 [PMID: 22142545]
type: SyntheticOrganicLigand

compound 23 [PMID: 17125252]
canonical SMILES: NCc1ccc(s1)c1ccccc1
isomeric SMILES: NCc1ccc(s1)c1ccccc1
in ch i key: PKRPFYKLLXGKDE-UHFFFAOYSA-N
in ch i: InChI=1S/C11H11NS/c12-8-10-6-7-11(13-10)9-4-2-1-3-5-9/h1-7H,8,12H2
comment: Compound 23 is a <Ligand id=2585/> analogue which inhibits the major nicotine metabolising enzyme, cytochrome P450 2A6 (CYP2A6) <Reference id=29736/>.
iupac name: (5-phenylthiophen-2-yl)methanamine
xref: CHEMBL215134
approved: f
ligand name: compound 23 [PMID: 17125252]
type: SyntheticOrganicLigand

compound 38a [PMID: 15634016]
canonical SMILES: NCc1ccc(s1)c1cccnc1
isomeric SMILES: NCc1ccc(s1)c1cccnc1
in ch i key: JHLIGYPHPBLDDL-UHFFFAOYSA-N
in ch i: InChI=1S/C10H10N2S/c11-6-9-3-4-10(13-9)8-2-1-5-12-7-8/h1-5,7H,6,11H2
comment: Compound 38a is a potent and reasonably selective inhibitor of human cytochrome P450 2A6 (CYP2A6), structurally related to <Ligand id=2585/> <Reference id=29735/>.
iupac name: (5-pyridin-3-ylthiophen-2-yl)methanamine
xref: CHEMBL359657
approved: f
ligand name: compound 38a [PMID: 15634016]
type: SyntheticOrganicLigand

compound 39a [PMID: 15634016]
canonical SMILES: NCc1ccc(o1)c1cccnc1
isomeric SMILES: NCc1ccc(o1)c1cccnc1
in ch i key: LENAVORGWBTPJR-UHFFFAOYSA-N
in ch i: InChI=1S/C10H10N2O/c11-6-9-3-4-10(13-9)8-2-1-5-12-7-8/h1-5,7H,6,11H2
comment: Compound 39a is a potent and reasonably selective inhibitor of human cytochrome P450 2A6 (CYP2A6), structurally related to <Ligand id=2585/> <Reference id=29735/>.
iupac name: (5-pyridin-3-ylfuran-2-yl)methanamine
xref: CHEMBL178090
approved: f
ligand name: compound 39a [PMID: 15634016]
type: SyntheticOrganicLigand

compound 10a [PMID: 1447738]
in ch i key: TYYCNSUODPEVQP-UHFFFAOYSA-N
in ch i: InChI=1S/C22H29FN2O4S/c23-20-10-12-21(13-11-20)30(28,29)25-16-2-1-5-18(9-14-22(26)27)6-3-7-19-8-4-15-24-17-19/h4,8,10-13,15,17-18,25H,1-3,5-7,9,14,16H2,(H,26,27)
comment: Compound 10a acts as an inhibitor of thromboxane-A synthase (CYP5A1) and as an antagonist of thromboxane receptors in human washed platelets <Reference id=29729/>.
iupac name: 8-[(4-fluorophenyl)sulfonylamino]-4-(3-pyridin-3-ylpropyl)octanoic acid
xref: CHEMBL136762
approved: f
ligand name: compound 10a [PMID: 1447738]
type: SyntheticOrganicLigand

ML355
in ch i key: OWHBVKBNNRYMIN-UHFFFAOYSA-N
in ch i: InChI=1S/C21H19N3O4S2/c1-28-18-7-4-5-14(20(18)25)13-22-15-9-11-16(12-10-15)30(26,27)24-21-23-17-6-2-3-8-19(17)29-21/h2-12,22,25H,13H2,1H3,(H,23,24)
comment: ML355 (compound 35 in the referenced article) inhibits the activity of arachidonate 12-lipoxygenase (12S-LOX, ALOX12), with selectivity compared to other LOX enzymes tested <Reference id=29727/>.
xref: CHEMBL3113165
synonym: ML-355
approved: f
ligand name: ML355
type: SyntheticOrganicLigand

compound 34 [PMID: 20866075]
in ch i key: PYNKKMZSVFDYAC-UHFFFAOYSA-N
in ch i: InChI=1S/C24H18N2O4S/c1-28-19-13-11-18(12-14-19)23(27)29-15-4-5-16-31-24-26-25-22(30-24)21-10-6-8-17-7-2-3-9-20(17)21/h2-3,6-14H,15-16H2,1H3
comment: Compound 34 is a potent, reversible and selective inhibitor of 15-LOX-1 (ALOX15) <Reference id=29724/>.
iupac name: 4-[(5-naphthalen-1-yl-1,3,4-oxadiazol-2-yl)sulfanyl]but-2-ynyl 4-methoxybenzoate
xref: CHEMBL1269896
approved: f
ligand name: compound 34 [PMID: 20866075]
type: SyntheticOrganicLigand

(4Z)-1-(3-fluorophenyl)-4-(2-oxo-1H-indol-3-ylidene)pyrazolidine-3,5-dione
isomeric SMILES: Fc1cccc(c1)N1NC(=O)/C(=C/2/C(=O)Nc3c2cccc3)/C1=O
in ch i key: CDNIIUJDSUXPEZ-YPKPFQOOSA-N
in ch i: InChI=1S/C17H10FN3O3/c18-9-4-3-5-10(8-9)21-17(24)14(16(23)20-21)13-11-6-1-2-7-12(11)19-15(13)22/h1-8H,(H,19,22)(H,20,23)/b14-13-
comment: This compound is a small molecule, reversible inhibitor of the regulator of G-protein signaling 4 (RGS4) protein.
iupac name: (4Z)-1-(3-fluorophenyl)-4-(2-oxo-1H-indol-3-ylidene)pyrazolidine-3,5-dione
xref: CHEMBL1381152
approved: f
ligand name: (4Z)-1-(3-fluorophenyl)-4-(2-oxo-1H-indol-3-ylidene)pyrazolidine-3,5-dione
type: SyntheticOrganicLigand

compound 21n [PMID: 17656086]
in ch i key: YCOQGGMZWKBBGI-UIDYPRJRSA-N
comment: Compound 21n inhibits 15-lipoxygenase 2 (ALOX15B) in a cellular assay <Reference id=29722/>.
iupac name: 5-[2-[[ethyl-[(3R)-1-[1-(4-fluorophenyl)ethyl]pyrrolidin-3-yl]sulfamoyl]amino]ethyl]-4-(4-methoxyphenyl)-2-thiophen-2-yl-1H-imidazole
xref: CHEMBL235920
approved: f
ligand name: compound 21n [PMID: 17656086]
type: SyntheticOrganicLigand

compound 30 [PMID: 22239545]
canonical SMILES: Cc1ccc2c(c1)[nH]c(n2)SCc1ccccn1
isomeric SMILES: Cc1ccc2c(c1)[nH]c(n2)SCc1ccccn1
in ch i key: RRLQDVNNRUSNKR-UHFFFAOYSA-N
in ch i: InChI=1S/C14H13N3S/c1-10-5-6-12-13(8-10)17-14(16-12)18-9-11-4-2-3-7-15-11/h2-8H,9H2,1H3,(H,16,17)
comment: Compound 30 was designed to inhibit cytochrome P450 2C19 (CYP2C19) <Reference id=29719/>. It is a structural analogue of <Ligand id=4279/>.
iupac name: 6-methyl-2-(pyridin-2-ylmethylsulfanyl)-1H-benzimidazole
xref: CHEMBL2019024
approved: f
ligand name: compound 30 [PMID: 22239545]
type: SyntheticOrganicLigand

5H3'FPE
canonical SMILES: C#CCOc1cccc(c1)c1cc(=O)c2c(o1)cccc2O
isomeric SMILES: C#CCOc1cccc(c1)c1cc(=O)c2c(o1)cccc2O
in ch i key: OCMGAXUTMOJVBQ-UHFFFAOYSA-N
in ch i: InChI=1S/C18H12O4/c1-2-9-21-13-6-3-5-12(10-13)17-11-15(20)18-14(19)7-4-8-16(18)22-17/h1,3-8,10-11,19H,9H2
comment: 5H3'FPE is a potent inhibitor of cytochrome P450 enzymes 1B1 (CYP1B1), 1A1 (CYP1A1) and 1A2 (CYP1A2) (in order of decreasing potency) <Reference id=29717/>.
iupac name: 5-hydroxy-2-(3-prop-2-ynoxyphenyl)chromen-4-one
xref: CHEMBL2347914
approved: f
ligand name: 5H3'FPE
type: SyntheticOrganicLigand

compound 3 [PMID: 18255300]
in ch i key: UQTXCTDQSVOMGL-UHFFFAOYSA-N
in ch i: InChI=1S/C19H14I2O4/c1-2-5-15-16(18(23)11-6-3-4-7-14(11)25-15)17(22)10-8-12(20)19(24)13(21)9-10/h3-4,6-9,24H,2,5H2,1H3
comment: Compound 3 potently binds cytochrome P450 2C9 <Reference id=29713/>.
iupac name: 3-(4-hydroxy-3,5-diiodobenzoyl)-2-propylchromen-4-one
xref: CHEMBL456432
approved: f
ligand name: compound 3 [PMID: 18255300]
type: SyntheticOrganicLigand

ajmalicine
in ch i key: GRTOGORTSDXSFK-XJTZBENFSA-N
in ch i: InChI=1S/C21H24N2O3/c1-12-16-10-23-8-7-14-13-5-3-4-6-18(13)22-20(14)19(23)9-15(16)17(11-26-12)21(24)25-2/h3-6,11-12,15-16,19,22H,7-10H2,1-2H3/t12-,15-,16+,19-/m0/s1
comment: An extract of the Rauwolfia serpentina plant (Indian snakeroot). Structurally related to <Ligand id=102/>.
xref: CHEMBL123325
synonym: delta-yohimbine
synonym: rauvasan
synonym: raubasine
synonym: rauwolfia alkaloid
approved: t
ligand name: ajmalicine
type: NaturalProductLigand

compound 3 [PMID: 21650226]
isomeric SMILES: O=C1NC(=O)/C(=C/c2ccc(c(c2)Cl)OCCC2CCCCC2)/S1
in ch i key: DBBGLVJTGXKCHY-WJDWOHSUSA-N
in ch i: InChI=1S/C18H20ClNO3S/c19-14-10-13(11-16-17(21)20-18(22)24-16)6-7-15(14)23-9-8-12-4-2-1-3-5-12/h6-7,10-12H,1-5,8-9H2,(H,20,21,22)/b16-11-
comment: Compound 3 is reported as a thiazolidinedione analogue inhibitor of 15-hydroxyprostaglandin dehydrogenase (HPGD) <Reference id=29704/>. This compound is also example 11 in patent US8637558 B2, which describes its use for the prevention or treatment of cardiovascular disease, gastrointestinal disease, renal disease and other conditions by increasing prostaglandin levels via inhibition of HPGD-induced prostaglandin metabolism <Reference id=29705/>.
iupac name: (5Z)-5-[[3-chloro-4-(2-cyclohexylethoxy)phenyl]methylidene]-1,3-thiazolidine-2,4-dione
xref: CHEMBL1800139
approved: f
ligand name: compound 3 [PMID: 21650226]
type: SyntheticOrganicLigand

compound 6a [PMID: 18942826]
canonical SMILES: OC(=O)c1ccnc(c1)C(=O)O
isomeric SMILES: OC(=O)c1ccnc(c1)C(=O)O
in ch i key: MJIVRKPEXXHNJT-UHFFFAOYSA-N
in ch i: InChI=1S/C7H5NO4/c9-6(10)4-1-2-8-5(3-4)7(11)12/h1-3H,(H,9,10)(H,11,12)
comment: Compound 6a inhibits the demethylase activity of lysine (K)-specific demethylase 4E (KDM4E, a.k.a. JMJD2E) and lysine (K)-specific demethylase 4A (KDM4A, a.k.a. JMJD2A) <Reference id=29703/>.
iupac name: pyridine-2,4-dicarboxylic acid
xref: CHEMBL316034
synonym: lutidinic acid
approved: f
ligand name: compound 6a [PMID: 18942826]
type: SyntheticOrganicLigand

compound 34 [PMID: 20189382]
in ch i key: YKPDLYPZCGMXBO-UHFFFAOYSA-N
in ch i: InChI=1S/C19H21N3O2S/c20-16-15-14(13-9-6-10-24-13)11-7-4-2-1-3-5-8-12(11)22-19(15)25-17(16)18(21)23/h6,9-10H,1-5,7-8,20H2,(H2,21,23)
comment: This is the most potent in vitro inhibitor of eukaryotic elongation factor 2 kinase (EEF2K) reported in <Reference id=29702/>.
xref: CHEMBL1092820
approved: f
ligand name: compound 34 [PMID: 20189382]
type: SyntheticOrganicLigand

VS-4718
in ch i key: IGUBBWJDMLCRIK-UHFFFAOYSA-N
in ch i: InChI=1S/C25H26F3N5O3/c1-29-24(34)17-5-3-4-6-19(17)31-21-14-23(30-15-18(21)25(26,27)28)32-20-8-7-16(13-22(20)35-2)33-9-11-36-12-10-33/h3-8,13-15H,9-12H2,1-2H3,(H,29,34)(H2,30,31,32)
comment: VS-4718 is an investigational, potent, reversible and orally active inhibitor of focal adhesion kinase (FAK; PTK2) <Reference id=29684/>. FAK inhibitors are being investigated for their anti-cancer effects due to the association of increased FAK expression with tumor progression, and the links between integrins and FAK in the adhesion pathways <Reference id=26183/>.
iupac name: 2-[[2-(2-methoxy-4-morpholin-4-ylanilino)-5-(trifluoromethyl)pyridin-4-yl]amino]-N-methylbenzamide
xref: CHEMBL3040440
synonym: PND-1186
synonym: PND 1186
synonym: PND1186
approved: f
ligand name: VS-4718
type: SyntheticOrganicLigand

resveratrol
canonical SMILES: Oc1ccc(cc1)C=Cc1cc(O)cc(c1)O
isomeric SMILES: Oc1ccc(cc1)/C=C/c1cc(O)cc(c1)O
in ch i key: LUKBXSAWLPMMSZ-OWOJBTEDSA-N
in ch i: InChI=1S/C14H12O3/c15-12-5-3-10(4-6-12)1-2-11-7-13(16)9-14(17)8-11/h1-9,15-17H/b2-1+
comment: Resveratrol is a natural product found in the skins of grapes and some other berries used predominantly as an antioxidant dietery supplement <Reference id=29677/><Reference id=29676/><Reference id=29675/>. The compound exists as a mixture of trans- (shown here) and cis- (PubChem CID 1548910) conformations. Resveratrol has been investigated for its various roles in complex biological processes <Reference id=29670/><Reference id=29671/><Reference id=29672/><Reference id=29673/><Reference id=29674/><Reference id=29678/><Reference id=29681/>. It has some activity as a cyclooxygenase inhibitor/antiinflammatory agent.
iupac name: 5-[(E)-2-(4-hydroxyphenyl)ethenyl]benzene-1,3-diol
xref: CHEMBL165
synonym: 3,4',5-stilbenetriol
synonym: 3,5,4'-trihydroxystilbene
synonym: trans-resveratrol
approved: f
ligand name: resveratrol
type: NaturalProductLigand

omecamtiv mecarbil
in ch i key: RFUBTTPMWSKEIW-UHFFFAOYSA-N
in ch i: InChI=1S/C20H24FN5O3/c1-14-6-7-16(12-22-14)23-19(27)24-17-5-3-4-15(18(17)21)13-25-8-10-26(11-9-25)20(28)29-2/h3-7,12H,8-11,13H2,1-2H3,(H2,23,24,27)
comment: Omecamtiv mecarbil is an investigational small molecule which is a direct activator of cardiac myosin <Reference id=29638/>. This compound is being investigated as a novel therapy for patients with chronic heart failure due to systolic dysfunction. Results from the first-in-man study are reported by Teerlink et al. (2011) <Reference id=29642/>. Omecamtiv mecarbil is claimed in patent US7507735 B2 <Reference id=29637/>.
iupac name: methyl 4-[[2-fluoro-3-[(6-methylpyridin-3-yl)carbamoylamino]phenyl]methyl]piperazine-1-carboxylate
xref: CHEMBL1800955
synonym: CK-1827452
synonym: AMG 423
synonym: AMG-423
approved: f
ligand name: omecamtiv mecarbil
type: SyntheticOrganicLigand

idalopirdine
in ch i key: YBAWYTYNMZWMMJ-UHFFFAOYSA-N
in ch i: InChI=1S/C20H19F5N2O/c21-15-4-5-17-14(11-27-18(17)9-15)6-7-26-10-13-2-1-3-16(8-13)28-12-20(24,25)19(22)23/h1-5,8-9,11,19,26-27H,6-7,10,12H2
comment: Idalopirdine is a serotonin 5-HT6 receptor antagonist <Reference id=29184/>.
xref: CHEMBL3286580
synonym: Lu AE58054
synonym: LU-AE58054
synonym: compound 52
approved: f
ligand name: idalopirdine
type: SyntheticOrganicLigand

oprozomib
in ch i key: SWZXEVABPLUDIO-WSZYKNRRSA-N
in ch i: InChI=1S/C25H32N4O7S/c1-15-26-11-20(37-15)24(33)29-19(13-35-4)23(32)28-18(12-34-3)22(31)27-17(21(30)25(2)14-36-25)10-16-8-6-5-7-9-16/h5-9,11,17-19H,10,12-14H2,1-4H3,(H,27,31)(H,28,32)(H,29,33)/t17-,18-,19-,25+/m0/s1
comment: Oprozomib is an orally bioavailable derivative of <Ligand id=7420/>, with similar biological action, i.e. inhibition of the chymotrypsin-like activity (a.k.a. β5 activity) of the proteasome <Reference id=29627/><Reference id=29629/>. This is compound 58 in <Reference id=29634/>.
iupac name: N-[(2S)-3-methoxy-1-[[(2S)-3-methoxy-1-[[(2S)-1-[(2R)-2-methyloxiran-2-yl]-1-oxo-3-phenylpropan-2-yl]amino]-1-oxopropan-2-yl]amino]-1-oxopropan-2-yl]-2-methyl-1,3-thiazole-5-carboxamide
synonym: ONX 0912
synonym: ONX-0912
synonym: PR 047
synonym: PR-047
approved: f
ligand name: oprozomib
type: SyntheticOrganicLigand

compound 4 [PMID: 26218264]
canonical SMILES: O=C(C(N)C)Nc1cccc(n1)N
isomeric SMILES: O=C([C@@H](N)C)Nc1cccc(n1)N
in ch i key: LRIKRUHIPRIMEM-YFKPBYRVSA-N
in ch i: InChI=1S/C8H12N4O/c1-5(9)8(13)12-7-4-2-3-6(10)11-7/h2-5H,9H2,1H3,(H3,10,11,12,13)/t5-/m0/s1
iupac name: (2S)-2-amino-N-(6-aminopyridin-2-yl)propanamide
approved: f
ligand name: compound 4 [PMID: 26218264]
type: SyntheticOrganicLigand

compound 4 [PMID: 26191369]
in ch i key: ZPVUIOVIUFJGHO-UHFFFAOYSA-N
in ch i: InChI=1S/C23H20FN5O2/c1-15-8-9-16(13-26-23(31)27-18-6-4-5-17(24)12-18)11-19(15)28-22(30)20-14-25-21-7-2-3-10-29(20)21/h2-12,14H,13H2,1H3,(H,28,30)(H2,26,27,31)
iupac name: N-[5-[[(3-fluorophenyl)carbamoylamino]methyl]-2-methylphenyl]imidazo[1,2-a]pyridine-3-carboxamide
approved: f
ligand name: compound 4 [PMID: 26191369]
type: SyntheticOrganicLigand

compound 33 [PMID: 26230603]
in ch i key: IMRGYBMGTASFSC-IAGOWNOFSA-N
in ch i: InChI=1S/C20H28N4O4S/c1-13-10-15-2-7-22-19(18(15)24-20(13)25)23-16-3-6-21-11-17(16)28-12-14-4-8-29(26,27)9-5-14/h2,7,10,14,16-17,21H,3-6,8-9,11-12H2,1H3,(H,22,23)(H,24,25)/t16-,17-/m1/s1
iupac name: 8-[[(3R,4R)-3-[(1,1-dioxothian-4-yl)methoxy]piperidin-4-yl]amino]-3-methyl-1H-1,7-naphthyridin-2-one
approved: f
ligand name: compound 33 [PMID: 26230603]
type: SyntheticOrganicLigand

compound 10b [PMID: 26222319]
canonical SMILES: COCCCN1Cc2c(C1=O)c(ccc2)C(=O)N
isomeric SMILES: COCCCN1Cc2c(C1=O)c(ccc2)C(=O)N
in ch i key: VARCSQSOWLMGTH-UHFFFAOYSA-N
in ch i: InChI=1S/C13H16N2O3/c1-18-7-3-6-15-8-9-4-2-5-10(12(14)16)11(9)13(15)17/h2,4-5H,3,6-8H2,1H3,(H2,14,16)
iupac name: 2-(3-methoxypropyl)-3-oxo-1H-isoindole-4-carboxamide
approved: f
ligand name: compound 10b [PMID: 26222319]
type: SyntheticOrganicLigand

(5Z)-5-[(5-bromothiophen-2-yl)methylidene]-1-methyl-2-sulfanylidene-1,3-diazinane-4,6-dione
canonical SMILES: Brc1ccc(s1)C=C1C(=O)NC(=S)N(C1=O)C
isomeric SMILES: Brc1ccc(s1)/C=C/1/C(=O)NC(=S)N(C1=O)C
in ch i key: DHXHBTASCMMTSD-XQRVVYSFSA-N
comment: This compound is a small molecule, reversible inhibitor of the regulator of G-protein signaling 4 (RGS4) protein.
iupac name: (5Z)-5-[(5-bromothiophen-2-yl)methylidene]-1-methyl-2-sulfanylidene-1,3-diazinane-4,6-dione
xref: CHEMBL1558954
approved: f
ligand name: (5Z)-5-[(5-bromothiophen-2-yl)methylidene]-1-methyl-2-sulfanylidene-1,3-diazinane-4,6-dione
type: SyntheticOrganicLigand

CCG-63808
isomeric SMILES: N#C/C(=C/c1c(Oc2ccc(cc2)F)nc2n(c1=O)cccc2C)/c1nc2c(s1)cccc2
in ch i key: IPZHFKHGSYRBNT-DTQAZKPQSA-N
in ch i: InChI=1S/C25H15FN4O2S/c1-15-5-4-12-30-22(15)29-23(32-18-10-8-17(26)9-11-18)19(25(30)31)13-16(14-27)24-28-20-6-2-3-7-21(20)33-24/h2-13H,1H3/b16-13+
comment: CCG-63808 is an allosteric, small molecule inhibitor of the regulator of G-protein signaling 4 (RGS4) protein <Reference id=29425/>.
iupac name: (E)-2-(1,3-benzothiazol-2-yl)-3-[2-(4-fluorophenoxy)-9-methyl-4-oxopyrido[1,2-a]pyrimidin-3-yl]prop-2-enenitrile
xref: CHEMBL1604848
approved: f
ligand name: CCG-63808
type: SyntheticOrganicLigand

CCG-63802
isomeric SMILES: N#C/C(=C/c1c(Oc2cccc(c2)C)nc2n(c1=O)cccc2C)/c1nc2c(s1)cccc2
in ch i key: VFSVKVQMZDJFQX-NBVRZTHBSA-N
in ch i: InChI=1S/C26H18N4O2S/c1-16-7-5-9-19(13-16)32-24-20(26(31)30-12-6-8-17(2)23(30)29-24)14-18(15-27)25-28-21-10-3-4-11-22(21)33-25/h3-14H,1-2H3/b18-14+
comment: CCG-63802 is a small molecule, allosteric inhibitor of the regulator of G-protein signaling 4 (RGS4) protein <Reference id=29425/>.
iupac name: (E)-2-(1,3-benzothiazol-2-yl)-3-[9-methyl-2-(3-methylphenoxy)-4-oxopyrido[1,2-a]pyrimidin-3-yl]prop-2-enenitrile
xref: CHEMBL1476646
approved: f
ligand name: CCG-63802
type: SyntheticOrganicLigand

CCG-4986
isomeric SMILES: CO/S(=N/S(=O)(=O)c1ccc(cc1)Cl)/c1ccc(cc1)[N+](=O)[O-]
in ch i key: GIFNUYPIOIDEGE-UHFFFAOYSA-N
comment: CCG-4986 is a small molecule allosteric inhibitor of the regulator of G-protein signaling 4 (RGS4) protein <Reference id=29421/>.
iupac name: (NE)-4-chloro-N-[methoxy-(4-nitrophenyl)-$l^{4}-sulfanylidene]benzenesulfonamide
synonym: compound 1
approved: f
ligand name: CCG-4986
type: SyntheticOrganicLigand

pexidartinib
in ch i key: JGWRKYUXBBNENE-UHFFFAOYSA-N
in ch i: InChI=1S/C20H15ClF3N5/c21-15-6-16-14(10-28-19(16)29-11-15)5-12-2-4-18(26-7-12)27-9-13-1-3-17(25-8-13)20(22,23)24/h1-4,6-8,10-11H,5,9H2,(H,26,27)(H,28,29)
comment: Pexidartinib is an orally available, multi-targeted inhibitor of the receptor tyrosine kinases, Fms-related tyrosine kinase 3 (FLT3), stem cell growth factor receptor (KIT) and colony stimulating factor 1 receptor (CSF1R), with potential antineoplastic activity <Reference id=30308/>. Pexidartinib is compound P-0181 in patent US7893075 B2 <Reference id=29384/>. It is active against wild type FLT3 and the FLT3 gatekeeper F691L resistance mutant, but its activity is vulnerable to mutations in the FLT3 activation loop <Reference id=37031/>.
iupac name: 5-[(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)methyl]-N-[[6-(trifluoromethyl)pyridin-3-yl]methyl]pyridin-2-amine
synonym: PLX3397
synonym: PLX-3397
synonym: PLX 3397
synonym: Turalio®
approved: t
ligand name: pexidartinib
type: SyntheticOrganicLigand

toxaphene
in ch i key: OEJNXTAZZBRGDN-UHFFFAOYSA-N
in ch i: InChI=1S/C10H8Cl8/c1-4-7(2-11,3-12)9(16)6(14)5(13)8(4,15)10(9,17)18/h5-6H,1-3H2
comment: Toxaphene is a complex mixture of hundreds of different chlorinated compounds. The structure shown here is representative of one of these compounds and is the same as the one displayed in the PubChem entry linked to above.
iupac name: 1,2,3,4,7,7-hexachloro-6,6-bis(chloromethyl)-5-methylidenebicyclo[2.2.1]heptane
xref: CHEMBL1566504
synonym: octachlorocamphene
approved: f
ligand name: toxaphene
type: SyntheticOrganicLigand

ozanimod
in ch i key: XRVDGNKRPOAQTN-FQEVSTJZSA-N
in ch i: InChI=1S/C23H24N4O3/c1-14(2)29-21-9-6-15(12-16(21)13-24)23-26-22(27-30-23)19-5-3-4-18-17(19)7-8-20(18)25-10-11-28/h3-6,9,12,14,20,25,28H,7-8,10-11H2,1-2H3/t20-/m0/s1
comment: Ozanimod (RPC1063) is a novel, orally available, specific and potent agonist of the sphingosine 1-phosphate 1 receptor (S1P1R) and SIP5Rs <Reference id=32471/>. Ozanimod is compound 86 in patent US20110172202 A1 <Reference id=29383/>, which specifies the (S)-enantiomer. Ozanimod reduces chronic inflammation and alleviates kidney pathology in a mouse model of systemic lupus erythematosus (SLE), which suggests that ozanimod may offer clinical benefit as a SLE therapeutic <Reference id=34722/>.
iupac name: 5-[3-[(1S)-1-(2-hydroxyethylamino)-2,3-dihydro-1H-inden-4-yl]-1,2,4-oxadiazol-5-yl]-2-propan-2-yloxybenzonitrile
synonym: Zeposia®
synonym: RPC1063
synonym: RPC-1063
synonym: RPC 1063
approved: t
ligand name: ozanimod
type: SyntheticOrganicLigand

gilteritinib
in ch i key: GYQYAJJFPNQOOW-UHFFFAOYSA-N
in ch i: InChI=1S/C29H44N8O3/c1-4-23-28(31-20-9-17-40-18-10-20)34-29(26(33-23)27(30)38)32-21-5-6-24(25(19-21)39-3)37-11-7-22(8-12-37)36-15-13-35(2)14-16-36/h5-6,19-20,22H,4,7-18H2,1-3H3,(H2,30,38)(H2,31,32,34)
comment: Gilteritinib is an orally bioavailable inhibitor of the receptor tyrosine kinases (RTKs) FMS-related tyrosine kinase 3 (FLT3), AXL and anaplastic lymphoma kinase (ALK) <Reference id=36515/>, with clinical antineoplastic activity. Gilteritinib inhibits the activity of FLT3-activating mutations which are one of the most common genetic alterations in acute myeloid leukemia (AML). SARS-CoV-2: AXL is a kinase upstream of p38 MAP kinases. p38 activity has been reported to be upregulated following SARS-CoV-2 infection of host cells in vitro, and gilteritinib produces an antiviral effect (IC50= 807 nM) <Reference id=39830/>.
iupac name: 6-ethyl-3-[3-methoxy-4-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]anilino]-5-(oxan-4-ylamino)pyrazine-2-carboxamide
xref: CHEMBL3301622
synonym: Xospata®
synonym: ASP-2215
synonym: ASP2215
approved: t
ligand name: gilteritinib
type: SyntheticOrganicLigand

deutetrabenazine
canonical SMILES: COc1cc2c(cc1OC)CCN1C2CC(=O)C(C1)CC(C)C
in ch i key: MKJIEFSOBYUXJB-VFJJUKLQSA-N
in ch i: InChI=1S/C19H27NO3/c1-12(2)7-14-11-20-6-5-13-8-18(22-3)19(23-4)9-15(13)16(20)10-17(14)21/h8-9,12,14,16H,5-7,10-11H2,1-4H3/t14-,16-/m1/s1/i3D3,4D3
comment: This is an orally available, deuterated analogue of <Ligand id=4834/> which can be administered in lower doses and in a simplified dosing regimen. Deutetrabenazine is the first ever deuterated drug to be approved. In drug discovery, replacing hydrogen atoms in drug compounds with deuterium (deuteration) is a technique employed to inhibit degradation of the drug and its active metabolites. The presence of the deuterium atoms attenuates CYP2D6-driven metabolic breakdown of the compound. This effects an increase in circulating half-lives and improves the duration of therapeutic effect and decreases the dose required to achieve therapeutic concentration <Reference id=31350/>.
iupac name: (3R,11bR)-3-(2-methylpropyl)-9,10-bis(trideuteriomethoxy)-1,3,4,6,7,11b-hexahydrobenzo[a]quinolizin-2-one
synonym: SD-809
synonym: SD809
synonym: tetrabenazine D6
synonym: Austedo®
approved: t
ligand name: deutetrabenazine
type: SyntheticOrganicLigand

compound 70 [PMID: 26161824]
in ch i key: VQXIVPLXEIZJTH-UHFFFAOYSA-N
comment: Compound 70 is a potent, peripherally acting, selective antagonist of the cannabinoid CB1 receptor, with much reduced adverse CNS effects than <Ligand id=743/>.
iupac name: 5-[4-(4-cyanobut-1-yn-1-yl)phenyl]-1-(2,4-dichlorophenyl)-4-(hydroxymethyl)-N-(morpholin-4-yl)-1H-pyrazole-3-carboxamide
approved: f
ligand name: compound 70 [PMID: 26161824]
type: SyntheticOrganicLigand

TM-38837
in ch i key: VQOCBFYUDSBDCZ-UHFFFAOYSA-N
comment: TM-38837 is a cannabinoid CB1 receptor selective inverse agonist/antagonist <Reference id=29330/>. This compound has been designed to be peripherally restricted so as to avoid the severe CNS side effects (depression, anxiety and stress disorders) which lead to the withdrawl of <Ligand id=743/>, the first CB1 receptor antagonist to receive marketing approval. TM-38837 has been investigated as a treatment for obesity and metabolic disorders.
synonym: compound 8
approved: f
ligand name: TM-38837
type: SyntheticOrganicLigand

emapunil
in ch i key: NBMBIEOUVBHEBM-UHFFFAOYSA-N
in ch i: InChI=1S/C23H23N5O2/c1-3-27(15-17-10-6-4-7-11-17)20(29)16-28-22-19(26(2)23(28)30)14-24-21(25-22)18-12-8-5-9-13-18/h4-14H,3,15-16H2,1-2H3
iupac name: N-ethyl-2-(7-methyl-8-oxo-2-phenylpurin-9-yl)-N-(phenylmethyl)acetamide
xref: CHEMBL513922
synonym: XBD-173
synonym: XBD173
synonym: AC-5216
approved: f
ligand name: emapunil
type: SyntheticOrganicLigand

PK 11195
in ch i key: RAVIZVQZGXBOQO-UHFFFAOYSA-N
in ch i: InChI=1S/C21H21ClN2O/c1-4-14(2)24(3)21(25)19-13-15-9-5-6-10-16(15)20(23-19)17-11-7-8-12-18(17)22/h5-14H,4H2,1-3H3
iupac name: N-butan-2-yl-1-(2-chlorophenyl)-N-methylisoquinoline-3-carboxamide
xref: CHEMBL481537
synonym: PK11195
synonym: PK-11195
approved: f
ligand name: PK 11195
type: SyntheticOrganicLigand

KML110
in ch i key: BBPOBHFPZPRPGB-UHFFFAOYSA-N
in ch i: InChI=1S/C22H23N3O3/c1-15-18-9-8-17(25(27)28)14-19(18)21(16-6-4-3-5-7-16)20(15)22(26)24-12-10-23(2)11-13-24/h3-9,14-15H,10-13H2,1-2H3
approved: f
ligand name: KML110
type: SyntheticOrganicLigand

tagitinin A
in ch i key: HREHFPZHVCNOMQ-XNNFIIJVSA-N
in ch i: InChI=1S/C19H28O7/c1-9(2)16(21)25-13-7-18(5)14(20)8-19(23,26-18)10(3)6-12-15(13)11(4)17(22)24-12/h9-10,12-15,20,23H,4,6-8H2,1-3,5H3/t10-,12+,13+,14-,15-,18+,19+/m0/s1
comment: Tagitinin A is a plant-derived sesquiterpene lactone isolated from Tithonia rotundifolia, which acts a dual activator of PPARα and PPARγ <Reference id=29222/>. This is one of the active components found in Chinese traditional medicines used to treat diabetes and hepatitis. Activation of PPARγ is responsible for the compound's anti-diabetic effect. Concomitant activation of PPARα may improve dyslipidemia.
xref: CHEMBL518700
approved: f
ligand name: tagitinin A
type: NaturalProductLigand

tirotundin
in ch i key: VKWNXJLVNFOOOS-QNIDSSLUSA-N
in ch i: InChI=1S/C19H28O6/c1-10(2)16(20)24-14-9-18(5)6-7-19(22,25-18)11(3)8-13-15(14)12(4)17(21)23-13/h10-11,13-15,22H,4,6-9H2,1-3,5H3/t11-,13+,14+,15-,18-,19+/m0/s1
comment: Tirotundin is a plant-derived sesquiterpene lactone isolated from Tithonia rotundifolia, which acts a dual activator of PPARα and PPARγ <Reference id=29222/>. This is one of the active components found in Chinese traditional medicines used to treat diabetes and hepatitis. Activation of PPARγ is responsible for the compound's anti-diabetic effect. Tirotundin-induced activation of PPARα may improve dyslipidemia.
xref: CHEMBL464453
approved: f
ligand name: tirotundin
type: NaturalProductLigand

verubecestat
in ch i key: YHYKUSGACIYRML-KRWDZBQOSA-N
comment: This is a new INN/USAN for a Merck BACE1 inhibitor for clinical trials in Alzheimer's disease (AD). Despite some early confusion surrounding the relationship between MK-8931, SCH 900931 and verubecestat, the article published by Scott et al. (2016) formally acknowledges verubecestat as MK-8931 <Reference id=33625/>. Despite reaching Phase 3 clinical trial, Merck has announced (Feb 2017: Merck press release) termination of study NCT01739348 (in patients with mild-moderate AD) because they concluded there was no chance of achieving efficacy. This is the latest of a long list of BACE1 inhibitors to fail in AD. Papers reporting trial outcomes were published in May 2018 <Reference id=35011/> and April 2019 <Reference id=37630/>.
iupac name: N-[3-[(5R)-3-amino-2,5-dimethyl-1,1-dioxo-6H-1,2,4-thiadiazin-5-yl]-4-fluorophenyl]-5-fluoropyridine-2-carboxamide
xref: CHEMBL3301601
synonym: MK-8931
synonym: MK8931
synonym: MK 8931
synonym: example 25 (US8940748)
approved: f
ligand name: verubecestat
type: SyntheticOrganicLigand

compound 16 [PMID: 23412139]
in ch i key: IJYPXSRDUPWKPB-SFHVURJKSA-N
in ch i: InChI=1S/C18H17ClN4OS/c1-4-5-11-6-12(10-21-9-11)14-7-13(19)16(25-14)18(2)8-15(24)23(3)17(20)22-18/h6-7,9-10H,8H2,1-3H3,(H2,20,22)/t18-/m0/s1
comment: This lead BACE1 inhibitor from Merck comes from the same paper <Reference id=27842/> that includes <Ligand id=8399/>.
iupac name: (6S)-2-amino-6-[3-chloro-5-(5-prop-1-ynylpyridin-3-yl)thiophen-2-yl]-3,6-dimethyl-5H-pyrimidin-4-one
xref: CHEMBL2151181
synonym: 0V6
approved: f
ligand name: compound 16 [PMID: 23412139]
type: SyntheticOrganicLigand

trifluridine
canonical SMILES: OCC1OC(CC1O)n1cc(c(=O)[nH]c1=O)C(F)(F)F
in ch i key: VSQQQLOSPVPRAZ-RRKCRQDMSA-N
in ch i: InChI=1S/C10H11F3N2O5/c11-10(12,13)4-2-15(9(19)14-8(4)18)7-1-5(17)6(3-16)20-7/h2,5-7,16-17H,1,3H2,(H,14,18,19)/t5-,6+,7+/m0/s1
comment: Trifluridine was originally approved by the US FDA in 1980, and was used for its antiviral effects (marketed as Vitroptic®). The drug is now being investigated for its antineoplastic (cytotoxic) effect.
iupac name: 1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-(trifluoromethyl)pyrimidine-2,4-dione
xref: CHEMBL1129
synonym: trifluorothymidine
synonym: TFT
approved: t
ligand name: trifluridine
type: SyntheticOrganicLigand

tipiracil
canonical SMILES: O=c1[nH]c(CN2CCCC2=N)c(c(=O)[nH]1)Cl
isomeric SMILES: O=c1[nH]c(CN2CCCC2=N)c(c(=O)[nH]1)Cl
in ch i key: QQHMKNYGKVVGCZ-UHFFFAOYSA-N
in ch i: InChI=1S/C9H11ClN4O2/c10-7-5(12-9(16)13-8(7)15)4-14-3-1-2-6(14)11/h11H,1-4H2,(H2,12,13,15,16)
comment: Tipracil is a a uracil derivative that inhibits thymidine phosphorylase (TYMP, P19971; a.k.a. platelet-derived endothelial cell growth factor), an enzyme which metabolises trifluridine. TAS-102 contains tipracil as the hydrochloride salt (PubChem CID 9903778). SARS-CoV-2: Tipracil has been shown to bind to the uridine-specific endoribonuclease Nsp15 of SARS-CoV-2, and this interaction inhibits the enzyme's uridine-degrading catalytic activity <Reference id=44175/>.
iupac name: 5-chloro-6-[(2-iminopyrrolidin-1-yl)methyl]-1H-pyrimidine-2,4-dione
xref: CHEMBL235668
synonym: TAS-1-462
synonym: MA-1
approved: t
ligand name: tipiracil
type: SyntheticOrganicLigand

evofosfamide
canonical SMILES: BrCCNP(=O)(NCCBr)OCc1cnc(n1C)[N+](=O)[O-]
isomeric SMILES: BrCCNP(=O)(NCCBr)OCc1cnc(n1C)[N+](=O)[O-]
in ch i key: UGJWRPJDTDGERK-UHFFFAOYSA-N
comment: Evofosfamide is a hypoxia-activated prodrug being investigated as an antineoplastic therapeutic (compound 3b in <Reference id=29206/>). This compound is related to <Ligand id=7201/>. Being developed by Threshold Pharmaceuticals.
iupac name: 2-bromo-N-[(2-bromoethylamino)-[(3-methyl-2-nitroimidazol-4-yl)methoxy]phosphoryl]ethanamine
xref: CHEMBL260046
synonym: TH-302
synonym: compound 3b
approved: f
ligand name: evofosfamide
type: SyntheticOrganicLigand

valbenazine
in ch i key: GEJDGVNQKABXKG-CFKGEZKQSA-N
in ch i: InChI=1S/C24H38N2O4/c1-14(2)9-17-13-26-8-7-16-10-21(28-5)22(29-6)11-18(16)19(26)12-20(17)30-24(27)23(25)15(3)4/h10-11,14-15,17,19-20,23H,7-9,12-13,25H2,1-6H3/t17-,19-,20-,23+/m1/s1
comment: Valbenazine is an analogue of <Ligand id=4834/>, which similarly selectively inhibits the monoamine transporter SLC18A2 (VMAT2). A search of patent literature reveals valbenazine as example 2-1 in US8357697 B2 <Reference id=29196/>.
iupac name: [(2R,3R,11bR)-9,10-dimethoxy-3-(2-methylpropyl)-2,3,4,6,7,11b-hexahydro-1H-pyrido[2,1-a]isoquinolin-2-yl] (2S)-2-amino-3-methylbutanoate
xref: CHEMBL2364639
synonym: NBI-98854
synonym: NBI98854
synonym: NBI 98854
synonym: Ingrezza®
approved: t
ligand name: valbenazine
type: SyntheticOrganicLigand

GSK9772
in ch i key: TYYLMKBOWXDDCT-UHFFFAOYSA-N
iupac name: 4-[[butyl-[4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)phenyl]amino]methyl]-2,6-dichlorophenol
xref: CHEMBL493241
synonym: GSK 9772
synonym: GSK-9772
approved: f
ligand name: GSK9772
type: SyntheticOrganicLigand

SR9238
in ch i key: HDZWHJYZJWLTAG-UHFFFAOYSA-N
in ch i: InChI=1S/C31H33NO7S2/c1-6-38-31(33)29-15-14-27(39-29)20-32(41(36,37)30-22(3)16-21(2)17-23(30)4)19-24-10-12-25(13-11-24)26-8-7-9-28(18-26)40(5,34)35/h7-18H,6,19-20H2,1-5H3
iupac name: ethyl 5-[[[4-(3-methylsulfonylphenyl)phenyl]methyl-(2,4,6-trimethylphenyl)sulfonylamino]methyl]furan-2-carboxylate
approved: f
ligand name: SR9238
type: SyntheticOrganicLigand

GSK2033
in ch i key: PSOXOVKYGWBTPB-UHFFFAOYSA-N
iupac name: 2,4,6-trimethyl-N-[[4-(3-methylsulfonylphenyl)phenyl]methyl]-N-[[5-(trifluoromethyl)furan-2-yl]methyl]benzenesulfonamide
xref: CHEMBL1093266
synonym: GSK 2033
synonym: GSK-2033
approved: f
ligand name: GSK2033
type: SyntheticOrganicLigand

hydroxyethylamine transition-state inhibitor 1
in ch i key: BNWZCXDHHPBQOX-XZWHSSHBSA-N
in ch i: InChI=1S/C33H32N2O3/c1-23-10-9-13-25(18-23)21-34-22-30(36)29(19-24-11-3-2-4-12-24)35-33(37)28-20-26-14-5-7-16-31(26)38-32-17-8-6-15-27(28)32/h2-18,20,29-30,34,36H,19,21-22H2,1H3,(H,35,37)/t29-,30+/m0/s1
comment: A hydroxyethylamine transition-state mimetic inhibitor of BACE2 with a crystal structure. This compound was initially identified as a BACE1 inhibitor by Novartis <Reference id=29177/>. A series of analogues is specified in a Novartis patent but without activity data <Reference id=29179/>.
iupac name: N-[(2S,3R)-3-hydroxy-4-[(3-methylphenyl)methylamino]-1-phenylbutan-2-yl]benzo[b][1]benzoxepine-6-carboxamide
approved: f
ligand name: hydroxyethylamine transition-state inhibitor 1
type: SyntheticOrganicLigand

ML380
in ch i key: FJPQEOQGIZSLES-UHFFFAOYSA-N
synonym: VU0481443-3
approved: f
ligand name: ML380
type: SyntheticOrganicLigand

Cl-amidine
canonical SMILES: ClCC(=N)NCCCC(C(=O)N)NC(=O)c1ccccc1
in ch i key: BPWATVWOHQZVRP-NSHDSACASA-N
in ch i: InChI=1S/C14H19ClN4O2/c15-9-12(16)18-8-4-7-11(13(17)20)19-14(21)10-5-2-1-3-6-10/h1-3,5-6,11H,4,7-9H2,(H2,16,18)(H2,17,20)(H,19,21)/t11-/m0/s1
comment: Cl-amidine is an inhihbitor of protein arginine deiminases (PADIs). Although reported to preferentially inhibit PADI1, isozyme selectivity is poor <Reference id=29097/>.
iupac name: N-[(2S)-1-amino-5-[(1-amino-2-chloroethylidene)amino]-1-oxopentan-2-yl]benzamide
xref: CHEMBL1962361
approved: f
ligand name: Cl-amidine
type: SyntheticOrganicLigand

compound 14b [PMID: 25742366]
in ch i key: TXEBWPPWSVMYOA-UHFFFAOYSA-N
comment: Compound 14b is reported as an irreversible and selective inhibitor of protein arginine deiminase type III (PADI3) <Reference id=29096/>.
iupac name: 4-{3-[(1-amino-2-chloroethyl)amino]propyl}-1-{[3-(2-chlorophenyl)phenyl]methyl}-5-hydroxyimidazolidin-2-one
approved: f
ligand name: compound 14b [PMID: 25742366]
type: SyntheticOrganicLigand

streptonigrin
in ch i key: DLWOTOMWYCRPLK-UVTDQMKNSA-N
in ch i: InChI=1S/C25H22N4O8/c1-9-14(10-6-8-13(35-2)23(36-3)20(10)30)15(26)19(29-17(9)25(33)34)12-7-5-11-18(28-12)22(32)16(27)24(37-4)21(11)31/h5-8,29H,26-27H2,1-4H3,(H,33,34)/b14-10-
comment: Streptonigrin is an antibacterial with anti-tumour effects ascribed to its substituted quinolinequinoic fragment <Reference id=29094/>. Streptonigrin is isolated from Streptomyces flocculus or S. rufochronmogenus. This compound is reported to be a selective inhibitor of protein-arginine deiminase type-IV (PADI4) <Reference id=29093/>. The ChEMBL entry for streptonigrin (CHEMBL11417) represents an alternative tautomer to the structure shown here.
iupac name: (4Z)-5-amino-6-(7-amino-6-methoxy-5,8-dioxoquinolin-2-yl)-4-(4,5-dimethoxy-6-oxocyclohexa-2,4-dien-1-ylidene)-3-methyl-1H-pyridine-2-carboxylic acid
synonym: rufocromomycin
synonym: bruneomycin
synonym: nigrin
synonym: valacidin
synonym: NSC-45383
approved: f
ligand name: streptonigrin
type: NaturalProductLigand

compound 3 [PMID: 24440480]
canonical SMILES: NC1=CC(=O)c2c(C1=O)nc(cc2)c1ccccn1
isomeric SMILES: NC1=CC(=O)c2c(C1=O)nc(cc2)c1ccccn1
in ch i key: UMMNKCUSQIKSGP-UHFFFAOYSA-N
in ch i: InChI=1S/C14H9N3O2/c15-9-7-12(18)8-4-5-11(17-13(8)14(9)19)10-3-1-2-6-16-10/h1-7H,15H2
comment: Compound 3 is reported as an irreversible pan-protein-arginine deiminase (PADI) inhibitor <Reference id=29093/>. Compound 3 is an analogue fragment of <Ligand id=8683/>.
iupac name: 7-amino-2-pyridin-2-ylquinoline-5,8-dione
xref: CHEMBL57818
approved: f
ligand name: compound 3 [PMID: 24440480]
type: SyntheticOrganicLigand

ANTAQ
in ch i key: SISSLRJYACXIQF-UHFFFAOYSA-N
in ch i: InChI=1S/C22H14N2O2/c25-21-18-11-5-6-12-19(18)23-22(26)24(21)20-16-9-3-1-7-14(16)13-15-8-2-4-10-17(15)20/h1-13H,(H,23,26)
comment: ANTAQ was developed as a probe to visualize puromycin-sensitive aminopeptidase (PSA, gene NPEPPS) in situ <Reference id=28961/> and acts as a selective PSA inhibitor.
iupac name: 3-anthracen-9-yl-1H-quinazoline-2,4-dione
xref: CHEMBL169736
synonym: compound 5
approved: f
ligand name: ANTAQ
type: SyntheticOrganicLigand

compound 5 [PMID: 21741839]
in ch i key: QKFCYPKTTJCUSZ-YADHBBJMSA-N
in ch i: InChI=1S/C26H36N8O4S/c27-23(28)20-12-10-18(11-13-20)16-32-24(35)22-9-5-15-34(22)25(36)21(8-4-14-31-26(29)30)33-39(37,38)17-19-6-2-1-3-7-19/h1-3,6-7,10-13,21-22,33H,4-5,8-9,14-17H2,(H3,27,28)(H,32,35)(H4,29,30,31)/t21-,22+/m1/s1
comment: Compound 5 is reported to inhibit the human airway trypsin-like protease HAT (TMPRSS11D) and the related transmembrane protease TMPRSS2 <Reference id=28960/>.
iupac name: (2S)-1-[(2R)-2-(benzylsulfonylamino)-5-(diaminomethylideneamino)pentanoyl]-N-[(4-carbamimidoylphenyl)methyl]pyrrolidine-2-carboxamide
xref: CHEMBL1229259
approved: f
ligand name: compound 5 [PMID: 21741839]
type: SyntheticOrganicLigand

volanesorsen
in ch i key: IJUQCWMZCMFFJP-GQSLRNSLSA-N
comment: Volanesorsen is an antisense oligonucleotide (ASO) designed to reduce levels of apolipoprotein C-III (APOC3) in patients with elevated blood triglyceride levels <Reference id=29060/>. Reducing triglycerides via APOC3 could be beneficial in patients with inherited hypertriglyceridemia (e.g. those with familial chylomicronemia syndrome, FCS) <Reference id=29061/>. The role of APOC3 in hypertriglyceridemia and the effects APOC3 ASO use are reviewed in <Reference id=29089/>. HELM annotation for this RNA (from PubChem) is RNA1{[MOE](A).[sp][MOE](G).[sp][MOE]([5meC]).[sp][MOE](T).[sp][MOE](T).[sp][dR]([5meC]).[sp][dR](T).[sp][dR](T).[sp][dR](G).[sp][dR](T).[sp][dR]([5meC]).[sp][dR]([5meC]).[sp][dR](A).[sp][dR](G).[sp][dR]([5meC]).[sp][MOE](T).[sp][MOE](T).[sp][MOE](T).[sp][MOE](A).[sp][MOE](T)}$$$$.
iupac name: Ade-MeOEt(-2)Ribf-sP-Gua-MeOEt(-2)Ribf-sP-m5Cyt-MeOEt(-2)Ribf-sP-Thy-MeOEt(-2)Ribf-sP-Thy-MeOEt(-2)Ribf-sP-m5Cyt-dRibf-sP-dThd-sP-dThd-sP-dGuo-sP-dThd-sP-m5Cyt-dRibf-sP-m5Cyt-dRibf-sP-dAdo-sP-dGuo-sP-m5Cyt-dRibf-sP-Thy-MeOEt(-2)Ribf-sP-Thy-MeOEt(-2)Ribf-sP-Thy-MeOEt(-2)Ribf-sP-Ade-MeOEt(-2)Ribf-sP-Thy-MeOEt(-2)Ribf
synonym: ISIS 304801
synonym: ISIS-APOCIIIRx
synonym: APOC-III antisense inhibitor
synonym: Waylivra®
approved: t
ligand name: volanesorsen
type: SyntheticOrganicLigand

IK-862
in ch i key: YDMIPBHQKFOFQW-NSYGIPOTSA-N
in ch i: InChI=1S/C25H27N3O4/c1-16-14-18(21-6-4-5-7-22(21)26-16)15-32-20-10-8-19(9-11-20)25(3)12-13-28(24(25)30)17(2)23(29)27-31/h4-11,14,17,31H,12-13,15H2,1-3H3,(H,27,29)/t17-,25+/m1/s1
comment: IK-862 selectively inhibits TACE (ADAM17), with the closest off-target being ADAM33 <Reference id=28948/>.
iupac name: (2R)-N-hydroxy-2-[(3S)-3-methyl-3-[4-[(2-methylquinolin-4-yl)methoxy]phenyl]-2-oxopyrrolidin-1-yl]propanamide
xref: CHEMBL148169
synonym: IK862
synonym: IK 862
synonym: compound 32
approved: f
ligand name: IK-862
type: SyntheticOrganicLigand

INCB3619
in ch i key: CKZHFOKQZRZCPF-ROUUACIJSA-N
in ch i: InChI=1S/C22H27N3O5/c1-30-21(28)25-14-22(9-10-22)13-17(19(26)23-29)18(25)20(27)24-11-7-16(8-12-24)15-5-3-2-4-6-15/h2-7,17-18,29H,8-14H2,1H3,(H,23,26)/t17-,18-/m0/s1
comment: INCB3619 was developed as an ADAM10 inhibitor, but also markedly inhibits ADAM17, MMP12 and MMP15 <Reference id=28948/>.
iupac name: methyl (5S,6S)-5-(hydroxycarbamoyl)-6-(4-phenyl3,6-dihydro-2H-pyridine-1-carbonyl)-7-azaspiro[2.5]octane-7-carboxylate
xref: CHEMBL434567
synonym: INCB-3619
synonym: compound 52
approved: f
ligand name: INCB3619
type: SyntheticOrganicLigand

finerenone
in ch i key: BTBHLEZXCOBLCY-QGZVFWFLSA-N
in ch i: InChI=1S/C21H22N4O3/c1-5-28-21-18-17(14-7-6-13(9-22)8-15(14)27-4)16(20(23)26)12(3)25-19(18)11(2)10-24-21/h6-8,10,17,25H,5H2,1-4H3,(H2,23,26)/t17-/m1/s1
comment: Finerenone (BAY 94-8862) is a next generation (first-in-class) oral, non-steroidal mineralocorticoid receptor antagonist which blocks the deleterious effects of aldosterone <Reference id=28997/>.
iupac name: (4S)-4-(4-cyano-2-methoxyphenyl)-5-ethoxy-2,8-dimethyl-1,4-dihydro-1,6-naphthyridine-3-carboxamide
synonym: BAY 94-8862
synonym: Kerendia®
approved: t
ligand name: finerenone
type: SyntheticOrganicLigand

compound 9 [PMID: 1738140]
canonical SMILES: OC(C(=O)NCCC(C)C)C(Cc1ccccc1)N
isomeric SMILES: O[C@H](C(=O)NCCC(C)C)[C@@H](Cc1ccccc1)N
in ch i key: WABAJXKDQWZIOJ-KGLIPLIRSA-N
in ch i: InChI=1S/C15H24N2O2/c1-11(2)8-9-17-15(19)14(18)13(16)10-12-6-4-3-5-7-12/h3-7,11,13-14,18H,8-10,16H2,1-2H3,(H,17,19)/t13-,14+/m1/s1
comment: Compound 9 selectively inhibits cytosolic aspartyl aminopeptidase (DNPEP) <Reference id=28992/>, relative to argininyl aminopeptidase (aminopeptidase B, RNPEP) and microsomal aminopeptidase N (ANPEP).
iupac name: (2S,3R)-3-amino-2-hydroxy-N-(3-methylbutyl)-4-phenylbutanamide
xref: CHEMBL309130
approved: f
ligand name: compound 9 [PMID: 1738140]
type: SyntheticOrganicLigand

S-BMPA
canonical SMILES: SCC(C(=O)O)Cc1ccccc1
isomeric SMILES: SC[C@H](C(=O)O)Cc1ccccc1
in ch i key: ZUEBVBPVXLQMQR-SECBINFHSA-N
in ch i: InChI=1S/C10H12O2S/c11-10(12)9(7-13)6-8-4-2-1-3-5-8/h1-5,9,13H,6-7H2,(H,11,12)/t9-/m1/s1
comment: S-BMPA is reported as the active enantiomer for inhibition of carboxypeptidase A <Reference id=28981/>.
iupac name: (2S)-2-(phenylmethyl)-3-sulfanylpropanoic acid
xref: CHEMBL90403
approved: f
ligand name: S-BMPA
type: SyntheticOrganicLigand

compound 3 [PMID: 14640538]
canonical SMILES: SCC(C(=O)O)CSCCN=C(N)N
isomeric SMILES: SCC(C(=O)O)CSCCN=C(N)N
in ch i key: AKPKWZRKZOAAAZ-UHFFFAOYSA-N
in ch i: InChI=1S/C7H15N3O2S2/c8-7(9)10-1-2-14-4-5(3-13)6(11)12/h5,13H,1-4H2,(H,11,12)(H4,8,9,10)
comment: Compound 3 was developed as an inhibitor of the thrombin-activatable fibrinolysis inhibitor (plasma carboxypeptidase B2) <Reference id=28977/>.
iupac name: 2-[2-(diaminomethylideneamino)ethylsulfanylmethyl]-3-sulfanylpropanoic acid
synonym: mergepta
synonym: 2-Mmgetpa
synonym: 2-mercaptomethyl-3-guanidinoethylthiopropanoic acid
synonym: DL-2-mercaptomethyl-3-guanidinoethyl-thiopropanoic acid
synonym: MGTA
approved: f
ligand name: compound 3 [PMID: 14640538]
type: SyntheticOrganicLigand

WAY-255348
canonical SMILES: N#Cc1ccc(n1C)c1cc(F)c2c(c1)C(C)(C)C(=O)N2
isomeric SMILES: N#Cc1ccc(n1C)c1cc(F)c2c(c1)C(C)(C)C(=O)N2
in ch i key: KIOOLNRTWPFVHX-UHFFFAOYSA-N
in ch i: InChI=1S/C16H14FN3O/c1-16(2)11-6-9(7-12(17)14(11)19-15(16)21)13-5-4-10(8-18)20(13)3/h4-7H,1-3H3,(H,19,21)
iupac name: 5-(7-fluoro-3,3-dimethyl-2-oxo-1H-indol-5-yl)-1-methylpyrrole-2-carbonitrile
xref: CHEMBL407848
synonym: WAY 255348
synonym: WAY255348
approved: f
ligand name: WAY-255348
type: SyntheticOrganicLigand

compound 12c [PMID: 16516466]
in ch i key: BODLESUVCQEUII-UHFFFAOYSA-N
in ch i: InChI=1S/C25H28N4O4/c1-17-14-19(21-4-2-3-5-22(21)27-17)16-33-20-8-6-18(7-9-20)24(31)28-25(15-23(30)29-32)10-12-26-13-11-25/h2-9,14,26,32H,10-13,15-16H2,1H3,(H,28,31)(H,29,30)
comment: Compound 12c is reported in a study to find small molecule inhibitors of ADAM17 (TNF α-converting enzyme, or TACE) <Reference id=28946/>.
iupac name: N-[4-[2-(hydroxyamino)-2-oxoethyl]piperidin-4-yl]-4-[(2-methylquinolin-4-yl)methoxy]benzamide
xref: CHEMBL208009
approved: f
ligand name: compound 12c [PMID: 16516466]
type: SyntheticOrganicLigand

grassystatin A
in ch i key: JZYWSTGTBRHGTL-BIXXXADNSA-N
in ch i: InChI=1S/C58H95N9O16/c1-30(2)25-38(43(69)29-45(71)64-46(36(12)68)52(74)60-35(11)54(76)66(15)42(27-37-21-18-17-19-22-37)55(77)67-24-20-23-41(67)56(78)81-16)61-51(73)40(28-44(59)70)62-50(72)39(26-31(3)4)63-53(75)48(33(7)8)82-58(80)49(34(9)10)83-57(79)47(32(5)6)65(13)14/h17-19,21-22,30-36,38-43,46-49,68-69H,20,23-29H2,1-16H3,(H2,59,70)(H,60,74)(H,61,73)(H,62,72)(H,63,75)(H,64,71)/t35-,36+,38-,39-,40-,41-,42+,43-,46-,47-,48+,49-/m0/s1
comment: Grassystatin A is a bioactive compound isolated from marine cyanobacteria. It is a potent and selective inhibitor of cathepsin E <Reference id=28976/>.
iupac name: methyl (2S)-1-[(2R)-2-[[(2S)-2-[[(2S,3R)-2-[[(3S,4S)-4-[[(2S)-4-amino-2-[[(2S)-2-[[(2R)-2-[(2S)-2-[(2S)-2-(dimethylamino)-3-methylbutanoyl]oxy-3-methylbutanoyl]oxy-3-methylbutanoyl]amino]-4-methylpentanoyl]amino]-4-oxobutanoyl]amino]-3-hydroxy-6-methylheptanoyl]amino]-3-hydroxybutanoyl]amino]propanoyl]-methylamino]-3-phenylpropanoyl]pyrrolidine-2-carboxylate
xref: CHEMBL567893
approved: f
ligand name: grassystatin A
type: NaturalProductLigand

compound 1 [PMID: 18507370]
canonical SMILES: Oc1ccccc1C=Cc1ccc2c(n1)cccc2
isomeric SMILES: Oc1ccccc1/C=C/c1ccc2c(n1)cccc2
in ch i key: NXNDEWNGCMCWMA-BENRWUELSA-N
in ch i: InChI=1S/C17H13NO/c19-17-8-4-2-6-14(17)10-12-15-11-9-13-5-1-3-7-16(13)18-15/h1-12,19H/b12-10-
comment: Compound 1 selectively inhibits endothelin-converting enzyme 2 <Reference id=28731/>.
iupac name: (6E)-6-[(2E)-2-(1H-quinolin-2-ylidene)ethylidene]cyclohexa-2,4-dien-1-one
xref: CHEMBL487942
approved: f
ligand name: compound 1 [PMID: 18507370]
type: SyntheticOrganicLigand

hK2p01 derivative KLK2 inhibitor
in ch i key: BVRWWHKWGPOKPN-NXOPMQQOSA-N
in ch i: InChI=1S/C59H82N16O11/c1-32(2)49(75-54(82)43(22-13-14-24-60)71-56(84)45(26-36-16-7-6-8-17-36)72-53(81)44(70-50(78)33(3)61)23-15-25-64-59(62)63)58(86)74-47(28-38-30-66-42-21-12-10-19-40(38)42)57(85)73-46(27-37-29-65-41-20-11-9-18-39(37)41)55(83)69-35(5)52(80)68-34(4)51(79)67-31-48(76)77/h6-12,16-21,29-30,32-35,43-47,49,65-66H,13-15,22-28,31,60-61H2,1-5H3,(H,67,79)(H,68,80)(H,69,83)(H,70,78)(H,71,84)(H,72,81)(H,73,85)(H,74,86)(H,75,82)(H,76,77)(H4,62,63,64)/t33-,34-,35-,43-,44-,45-,46-,47-,49-/m0/s1
comment: hK2p01 derivative KLK2 inhibitor is an 11 amino acid substrate competitive inhibitor with selectivity for human kallikrein-related peptidase 2 <Reference id=28962/>.
iupac name: 2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-6-amino-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-aminopropanoyl]amino]-5-(diaminomethylideneamino)pentanoyl]amino]-3-phenylpropanoyl]amino]hexanoyl]amino]-3-methylbutanoyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]propanoyl]amino]propanoyl]amino]acetic acid
xref: CHEMBL2171880
approved: f
ligand name: hK2p01 derivative KLK2 inhibitor
type: PeptideLigand

vialinin A
in ch i key: NOJUKCRPSUMHQQ-UHFFFAOYSA-N
in ch i: InChI=1S/C34H26O8/c35-25-15-11-23(12-16-25)29-31(39)32(40)30(24-13-17-26(36)18-14-24)34(42-28(38)20-22-9-5-2-6-10-22)33(29)41-27(37)19-21-7-3-1-4-8-21/h1-18,35-36,39-40H,19-20H2
comment: Vialinin A, a naturally ocurring compound extracted from the Chinese mushroom Thelephora vialis, is reported to inhibit ubiquitin-specific peptidases <Reference id=28959/>. Vialinin A exhibits a potent anti-inflammatory effect.
iupac name: [3,4-dihydroxy-2,5-bis(4-hydroxyphenyl)-6-(2-phenylacetyl)oxyphenyl] 2-phenylacetate
xref: CHEMBL2012938
synonym: ganbajunin C
approved: f
ligand name: vialinin A
type: NaturalProductLigand

furin inhibitor peptide
in ch i key: XIHRZTWKTVFWSV-HQSWAJDZSA-N
comment: This 11 amino acid peptide is reported to inhibit furin and other furin-like proprotein convertases <Reference id=28958/>.
iupac name: (2S)-N-[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-6-amino-1-[[(2S)-6-amino-1-[[(2S)-1-[[(2S,3R)-1-amino-3-hydroxy-1-oxobutan-2-yl]amino]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]amino]-1-oxohexan-2-yl]amino]-1-oxohexan-2-yl]amino]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]amino]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]amino]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]amino]-1-oxopropan-2-yl]amino]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]-1-[(2S,3R)-2-amino-3-hydroxybutanoyl]pyrrolidine-2-carboxamide
xref: CHEMBL502642
approved: f
ligand name: furin inhibitor peptide
type: PeptideLigand

Lys-thiol
canonical SMILES: NCCCCC(C(=O)O)S
isomeric SMILES: NCCCCC(C(=O)O)S
in ch i key: JNQDJHCXDRGZJD-UHFFFAOYSA-N
in ch i: InChI=1S/C6H13NO2S/c7-4-2-1-3-5(10)6(8)9/h5,10H,1-4,7H2,(H,8,9)
comment: Lys-thiol is reported to be a potent inhibitor of aminopeptidase B <Reference id=28956/>.
iupac name: 6-amino-2-sulfanylhexanoic acid
xref: CHEMBL432852
approved: f
ligand name: Lys-thiol
type: SyntheticOrganicLigand

compound 17 [PMID: 23916253]
in ch i key: XPUCDWKMNQBXIH-OALUTQOASA-N
in ch i: InChI=1S/C23H31N5O4/c24-13-5-4-8-19(23(31)32)27-21(29)16-10-12-17(25)20(14-16)28-22(30)18(26)11-9-15-6-2-1-3-7-15/h1-3,6-7,10,12,14,18-19H,4-5,8-9,11,13,24-26H2,(H,27,29)(H,28,30)(H,31,32)/t18-,19-/m0/s1
comment: Compound 17 is reported from a structure-activity study to identify novel aminopeptidase inhibitors that improve antigen processing <Reference id=28950/>, principally by inhibiting the endoplasmic reticulum aminopeptidases, ERAP1 and ERAP2, as well as the insulin regulated aminopeptidase IRAP (LNPEP).
iupac name: (2S)-6-amino-2-[[4-amino-3-[[(2S)-2-amino-4-phenylbutanoyl]amino]benzoyl]amino]hexanoic acid
xref: CHEMBL2420382
approved: f
ligand name: compound 17 [PMID: 23916253]
type: SyntheticOrganicLigand

compound 10 [PMID: 18790648]
in ch i key: YDDMVPLLJTZTQL-LAABSITASA-N
in ch i: InChI=1S/C38H41N4O7PS/c1-48-33-18-10-11-19-34(33)51-25-29(37(44)41-32(36(39)43)21-28-22-40-31-17-9-8-16-30(28)31)24-50(46,47)35(20-26-12-4-2-5-13-26)42-38(45)49-23-27-14-6-3-7-15-27/h2-19,22,29,32,35,40H,20-21,23-25H2,1H3,(H2,39,43)(H,41,44)(H,42,45)(H,46,47)/t29-,32-,35+/m0/s1
comment: Compound 10 was discovered in a study aiming to identify selective matrix metalloproteinase (MMP) inhibitors <Reference id=28948/>. Compound 10 is at least 100-fold selective for MMP11 compared to other MMPs tested.
iupac name: [(2S)-3-[[(2S)-1-amino-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-2-[(2-methoxyphenyl)sulfanylmethyl]-3-oxopropyl]-[(1R)-2-phenyl-1-(phenylmethoxycarbonylamino)ethyl]phosphinic acid
xref: CHEMBL447457
approved: f
ligand name: compound 10 [PMID: 18790648]
type: SyntheticOrganicLigand

APR19
in ch i key: UEILQXVVJHZGQK-KYFJQHFKSA-N
in ch i: InChI=1S/C21H32F2/c1-13-4-7-17-16-6-5-14-12-15(22)8-10-20(14,2)18(16)9-11-21(17,3)19(13)23/h5,13,15-19H,4,6-12H2,1-3H3/t13-,15+,16?,17?,18?,19+,20+,21+/m1/s1
iupac name: (1S,2R,8S,10aR,12aS)-1,8-difluoro-2,10a,12a-trimethyl-1,2,3,4,4a,4b,5,7,8,9,10,10b,11,12-tetradecahydrochrysene
approved: f
ligand name: APR19
type: SyntheticOrganicLigand

LDN-91946
in ch i key: OJHMDRZMENMQFP-UHFFFAOYSA-N
in ch i: InChI=1S/C15H10N2O4S/c16-10-8-6-9(15(20)21)13(19)17-14(8)22-12(10)11(18)7-4-2-1-3-5-7/h1-6H,16H2,(H,17,19)(H,20,21)
comment: LDN-91946 selectively inhibits ubiquitin carboxyl-terminal esterase L1 (ubiquitin thiolesterase, UCHL1) <Reference id=28938/><Reference id=28944/>.
iupac name: 3-amino-2-(benzoyl)-6-oxo-7H-thieno[3,2-e]pyridine-5-carboxylic acid
xref: CHEMBL1190585
synonym: compound 7
approved: f
ligand name: LDN-91946
type: SyntheticOrganicLigand

compound 6 [PMID: 17948018]
canonical SMILES: O=C1CC(=O)c2c1c(Cl)c(c(c2Cl)Cl)Cl
isomeric SMILES: O=C1CC(=O)c2c1c(Cl)c(c(c2Cl)Cl)Cl
in ch i key: IDLAOWFFKWRNHB-UHFFFAOYSA-N
in ch i: InChI=1S/C9H2Cl4O2/c10-6-4-2(14)1-3(15)5(4)7(11)9(13)8(6)12/h1H2
comment: Compound 6 is reported to inhibit ubiquitin carboxyl-terminal esterase L3 (UCHL3) with >100-fold selectivity over the L2 isozyme (UCHL2) <Reference id=28938/>.
iupac name: 4,5,6,7-tetrachloroindene-1,3-dione
xref: CHEMBL1241028
approved: f
ligand name: compound 6 [PMID: 17948018]
type: SyntheticOrganicLigand

compound 8d [PMID: 15027864]
in ch i key: QXWVJRPYHOYHHT-QWRGUYRKSA-N
in ch i: InChI=1S/C15H18N2O8/c18-9-3-1-8(2-4-9)7-11(14(23)24)17-15(25)16-10(13(21)22)5-6-12(19)20/h1-4,10-11,18H,5-7H2,(H,19,20)(H,21,22)(H,23,24)(H2,16,17,25)/t10-,11-/m0/s1
comment: Compound 8d is reported as the lead compound in a study to find inhibitors of the neuropeptidase glutamate carboxypeptidase II (GCPII, which is encoded by the FOLH1 gene) which have drug-like pharmacokinetic and pharmacodynamic properties, in particular having the ability to cross the blood-brain barrier <Reference id=28936/>. FOLH1 inhibitors have been investigated for their potential to treat conditions such as neuropathic and inflammatory pain, head injury, stroke, schizophrenia, diabetic neuropathy, prostate cancer, and neurodegenerative diseases.
iupac name: (2S)-2-[[(2S)-1-hydroxy-3-(4-hydroxyphenyl)-1-oxopropan-2-yl]carbamoylamino]pentanedioic acid
xref: CHEMBL297489
approved: f
ligand name: compound 8d [PMID: 15027864]
type: SyntheticOrganicLigand

peptide 18 [PMID: 24350995]
in ch i key: UFNWIBYSOUCSGW-FVMQRRFMSA-N
in ch i: InChI=1S/C51H90N14O8/c1-28(2)23-38(59-33(11)66)46(69)62-40(25-30(5)6)48(71)64-41(26-31(7)8)49(72)63-39(24-29(3)4)47(70)60-37(16-14-22-57-51(55)56)45(68)65-42(32(9)10)50(73)61-36(15-12-13-21-52)44(67)58-27-34-17-19-35(20-18-34)43(53)54/h17-20,28-32,36-42H,12-16,21-27,52H2,1-11H3,(H3,53,54)(H,58,67)(H,59,66)(H,60,70)(H,61,73)(H,62,69)(H,63,72)(H,64,71)(H,65,68)(H4,55,56,57)/t36-,37-,38-,39-,40-,41-,42-/m0/s1
comment: This peptide is a modified, and optimised analogue of <Ligand id=8648/>, with an arginine mimetic at the P1 position (i.e. at the N-terminal arginine) <Reference id=28935/>.
xref: CHEMBL3115771
synonym: Ac-LLLLRVK-Amba
approved: f
ligand name: peptide 18 [PMID: 24350995]
type: SyntheticOrganicLigand

UK-396,082
canonical SMILES: CCCn1cnc(c1)CC(C(=O)O)CCCN
isomeric SMILES: CCCn1cnc(c1)C[C@@H](C(=O)O)CCCN
in ch i key: OTDGPKRCQXSTPV-JTQLQIEISA-N
in ch i: InChI=1S/C12H21N3O2/c1-2-6-15-8-11(14-9-15)7-10(12(16)17)4-3-5-13/h8-10H,2-7,13H2,1H3,(H,16,17)/t10-/m0/s1
comment: UK-396,082 is reported as a selective inhibitor of human thrombin-activatable fibrinolysis inhibitor (TAFI, CPB2) with >1000-fold selectivity over carboxypeptidase N <Reference id=28932/>.
iupac name: (2S)-5-amino-2-[(1-propylimidazol-4-yl)methyl]pentanoic acid
xref: CHEMBL398110
synonym: UK-396082
synonym: compound 21 [PMID: 17990866]
approved: f
ligand name: UK-396,082
type: SyntheticOrganicLigand

SQ-24,798
canonical SMILES: SCC(C(=O)O)CCCN=C(N)N
isomeric SMILES: SCC(C(=O)O)CCCN=C(N)N
in ch i key: JOVIPJZDTSYNNW-UHFFFAOYSA-N
in ch i: InChI=1S/C7H15N3O2S/c8-7(9)10-3-1-2-5(4-13)6(11)12/h5,13H,1-4H2,(H,11,12)(H4,8,9,10)
comment: The discovery of SQ-24,798 is reported in <Reference id=28932/>, where it is shown to inhibit both the thrombin-activatable fibrinolysis inhibitor (TAFI, CPB2) and carboxypeptidase N (CPN).
iupac name: 5-(diaminomethylideneamino)-2-(sulfanylmethyl)pentanoic acid
xref: CHEMBL236822
synonym: SQ-24798
synonym: SQ 24,798
synonym: SQ 24798
synonym: compound 4
approved: f
ligand name: SQ-24,798
type: SyntheticOrganicLigand

compound 5 {PMID: 24900446]
in ch i key: KKFJNRXJRRYNRJ-VWLOTQADSA-N
in ch i: InChI=1S/C28H28N4O4S2/c1-36-22-9-7-20-8-11-24(16-21(20)15-22)38(34,35)32(17-19-5-3-2-4-6-19)25-13-14-31(28(25)33)18-23-10-12-26(37-23)27(29)30/h2-12,15-16,25H,13-14,17-18H2,1H3,(H3,29,30)/t25-/m0/s1
comment: Compound 5 is reported to inhibit the serine protease, human kallikrein 6 <Reference id=28927/>. Kallikrein 6 inhibitors are being investigated for their potential therapeutic value in treating inflammatory demyelinating diseases such as multiple sclerosis (MS).
iupac name: 5-[[(3S)-3-[benzyl-(7-methoxynaphthalen-2-yl)sulfonylamino]-2-oxopyrrolidin-1-yl]methyl]thiophene-2-carboximidamide
xref: CHEMBL2047313
approved: f
ligand name: compound 5 {PMID: 24900446]
type: SyntheticOrganicLigand

M826
in ch i key: XIMITGPWYYFUQF-UHFFFAOYSA-N
in ch i: InChI=1S/C28H45N7O6/c1-8-10-11-12-13-34(7)16-22(36)19(14-24(37)38)30-26(39)21(9-2)35-17-23(28(4,5)6)31-25(27(35)40)29-15-20-18(3)32-41-33-20/h17,19,21H,8-16H2,1-7H3,(H,29,31)(H,30,39)(H,37,38)
comment: The structure and function of M826 is reported by Han et al. (2005) <Reference id=28919/>. M826 inhibits the activity of human recombinant caspase in vitro.
iupac name: 3-[2-[5-tert-butyl-3-[(4-methyl-1,2,5-oxadiazol-3-yl)methylamino]-2-oxopyrazin-1-yl]butanoylamino]-5-(hexyl-methylamino)-4-oxopentanoic acid
xref: CHEMBL1184755
synonym: compound 4sx
approved: f
ligand name: M826
type: SyntheticOrganicLigand

compound 51 [PMID: 19743866]
in ch i key: VIJSPAIQWVPKQZ-BLECARSGSA-N
in ch i: InChI=1S/C36H68N12O8/c1-19(2)16-25(30(52)43-21(5)28(50)45-24(33(55)56)13-11-15-42-35(39)40)47-32(54)27(18-36(7,8)9)48-31(53)26(17-20(3)4)46-29(51)23(44-22(6)49)12-10-14-41-34(37)38/h19-21,23-27H,10-18H2,1-9H3,(H,43,52)(H,44,49)(H,45,50)(H,46,51)(H,47,54)(H,48,53)(H,55,56)(H4,37,38,41)(H4,39,40,42)/t21-,23-,24-,25-,26-,27-/m0/s1
comment: Compound 51 is a hexapeptide which potently inhibits complement factor B <Reference id=28914/>.
iupac name: (2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-acetamido-5-(diaminomethylideneamino)pentanoyl]amino]-4-methylpentanoyl]amino]-4,4-dimethylpentanoyl]amino]-4-methylpentanoyl]amino]propanoyl]amino]-5-(diaminomethylideneamino)pentanoic acid
xref: CHEMBL1089597
synonym: Ac-RLTbaLAR-H
approved: f
ligand name: compound 51 [PMID: 19743866]
type: SyntheticOrganicLigand

compound 20 [PMID:12127536]
in ch i key: UCXMBOHIKJZNMQ-GIYJSHOWSA-N
in ch i: InChI=1S/C34H38N6O8/c1-5-18(2)27(39(4)19(3)41)31(46)35-23-15-14-20-12-9-13-22-16-25(40(28(20)22)34(23)47)30(45)36-24(17-26(42)43)29(44)33-38-37-32(48-33)21-10-7-6-8-11-21/h6-13,18,23-25,27H,5,14-17H2,1-4H3,(H,35,46)(H,36,45)(H,42,43)/t18-,23-,24-,25-,27-/m0/s1
comment: Compound 20 is reported as an inhibitor of the serine protease, granzyme B (GZMB) <Reference id=28894/>.
xref: CHEMBL71654
approved: f
ligand name: compound 20 [PMID:12127536]
type: SyntheticOrganicLigand

HT1042
canonical SMILES: O=c1snc(o1)c1cccc(c1)[N+](=O)[O-]
isomeric SMILES: O=c1snc(o1)c1cccc(c1)[N+](=O)[O-]
in ch i key: QBAZATRGWRVUFN-UHFFFAOYSA-N
in ch i: InChI=1S/C8H4N2O4S/c11-8-14-7(9-15-8)5-2-1-3-6(4-5)10(12)13/h1-4H
comment: HT1042 is reported to inhibit the β5i component of the 20S proteasome complex <Reference id=28882/>, which is constitutively expressed in dendritic cells and lymphocytes, and is induced in other cells by some cytokines to modulate antigen presentation <Reference id=28888/>. Inhibitors selective for this immune system-associated 20S proteasome complex are expected to provide novel and more selective anti-inflammatory leads, compared to the current broad-spectrum proteasome inhibitor <Ligand id=6391/> used in the clinic.
iupac name: 5-(3-nitrophenyl)-1,3,4-oxathiazol-2-one
xref: CHEMBL3265177
approved: f
ligand name: HT1042
type: SyntheticOrganicLigand

multi-Leu (ML)-peptide
in ch i key: UQCOICUQZUWRMW-YYGRSCHNSA-N
in ch i: InChI=1S/C41H80N14O8/c1-22(2)19-26(43)33(56)53-30(20-23(3)4)37(60)54-31(21-24(5)6)36(59)50-28(14-11-17-48-40(44)45)35(58)55-32(25(7)8)38(61)51-27(13-9-10-16-42)34(57)52-29(39(62)63)15-12-18-49-41(46)47/h22-32H,9-21,42-43H2,1-8H3,(H,50,59)(H,51,61)(H,52,57)(H,53,56)(H,54,60)(H,55,58)(H,62,63)(H4,44,45,48)(H4,46,47,49)/t26-,27-,28-,29-,30-,31-,32-/m0/s1
comment: This ML-peptide is reported to inhibit proprotein convertase subtilisin/kexin type 6 (PACE4) with >20-fold selectivity over furin <Reference id=28876/>.
synonym: ML-peptide
approved: f
ligand name: multi-Leu (ML)-peptide
type: PeptideLigand

GSK312948
in ch i key: AWMDAFUCNYEZNI-CQSZACIVSA-N
comment: GSK312948 is an in vitro polo-like kinase inhibitor tool compound.
iupac name: 1-{3-[(1R)-1-(2-chlorophenyl)ethoxy]-5-(5,6-dimethoxy-1H-1,3-benzodiazol-1-yl)thiophen-2-yl}ethen-1-amine
approved: f
ligand name: GSK312948
type: SyntheticOrganicLigand

compound 2 [PMID: 19097784]
in ch i key: SYQIMXCJFHFKLG-UHFFFAOYSA-N
comment: Compound 2 is an in vitro polo-like kinase inhibitor tool compound <Reference id=28856/>.
approved: f
ligand name: compound 2 [PMID: 19097784]
type: SyntheticOrganicLigand

GW853606
in ch i key: LOKKVFGDJAVMLU-UHFFFAOYSA-N
comment: GW853606 is an inhibitor of the polo-like kinase, PLK1 <Reference id=28856/>.
iupac name: 3-[(2-bromophenyl)methoxy]-5-[6-(trifluoromethyl)benzimidazol-1-yl]thiophene-2-carboxamide
xref: CHEMBL481510
synonym: GW853606X
synonym: compound 22 [PMID: 19097784]
approved: f
ligand name: GW853606
type: SyntheticOrganicLigand

GSK1511931
in ch i key: PEPOAPKYASCEKL-UHFFFAOYSA-N
in ch i: InChI=1S/C29H32N8O/c1-19(2)36-14-16-37(17-15-36)20-9-10-25(26(18-20)38-3)33-29-34-27-22(11-13-31-27)28(35-29)32-24-8-4-7-23-21(24)6-5-12-30-23/h4-13,18-19H,14-17H2,1-3H3,(H3,31,32,33,34,35)
comment: GSK1511931 is an investigational IGF-1R inhibitor <Reference id=28852/>.
iupac name: 2-N-[2-methoxy-4-(4-propan-2-ylpiperazin-1-yl)phenyl]-4-N-quinolin-5-yl-7H-pyrrolo[2,3-d]pyrimidine-2,4-diamine
xref: CHEMBL458438
synonym: GSK1511931A
synonym: GSK-1511931
synonym: compound 14 [PMID: 19081716]
approved: f
ligand name: GSK1511931
type: SyntheticOrganicLigand

ZK216348
in ch i key: VRZVKIJRJRBQJT-UHFFFAOYSA-N
in ch i: InChI=1S/C24H23F3N2O5/c1-13-17-11-15(7-8-16(17)20(30)34-29-13)28-21(31)23(32,24(25,26)27)12-22(2,3)18-6-4-5-14-9-10-33-19(14)18/h4-8,11,32H,9-10,12H2,1-3H3,(H,28,31)
iupac name: 4-(2,3-dihydro-1-benzofuran-7-yl)-2-hydroxy-4-methyl-N-(4-methyl-1-oxo-2,3-benzoxazin-6-yl)-2-(trifluoromethyl)pentanamide
xref: CHEMBL216272
synonym: ZK 216348
synonym: ZK-216348
approved: f
ligand name: ZK216348
type: SyntheticOrganicLigand

SB-633825
in ch i key: ZDSNJSQTPLXCSG-UHFFFAOYSA-N
in ch i: InChI=1S/C28H25N3O3S/c1-18-15-24(35(4,32)33)9-10-25(18)28-30-26(19-11-13-29-14-12-19)27(31(28)2)22-6-5-21-17-23(34-3)8-7-20(21)16-22/h5-17H,1-4H3
comment: SB-633825 is a novel inhibitor of human serine/threonine kinase 10 (STK10). The crystal structure of SB-633825-bound STK10 has been deposited to the RSCB Protein Data Bank by the Structural Genomics Consortium (SGC- link here).
iupac name: 4-[5-(6-methoxynaphthalen-2-yl)-1-methyl-2-(2-methyl-4-methylsulfonylphenyl)imidazol-4-yl]pyridine
xref: CHEMBL237571
approved: f
ligand name: SB-633825
type: SyntheticOrganicLigand

compound 60 [PMID: 26155854]
in ch i key: FPQQERRFPULCIK-UHFFFAOYSA-N
in ch i: InChI=1S/C20H23N5O2/c1-12-7-16-17(13-8-15(27-2)10-22-9-13)11-23-19(18(16)25-20(12)26)24-14-3-5-21-6-4-14/h7-11,14,21H,3-6H2,1-2H3,(H,23,24)(H,25,26)
comment: Compound 60 is reported as a novel low-micromolar inhibitor of ATPase family, AAA domain containing 2 (ATAD2) <Reference id=28844/>. This compound has little selectivity over other BET domains tested so further optimisation would be required to optimise the selectivity profile ATAD2 inhibitors are being investigated for their potential anti-cancer effects.
iupac name: 5-(5-methoxypyridin-3-yl)-3-methyl-8-[(piperidin-4-yl)amino]-1,2-dihydro-1,7-naphthyridin-2-one
approved: f
ligand name: compound 60 [PMID: 26155854]
type: SyntheticOrganicLigand

compound 57 [PMID: 26155854]
in ch i key: PAGDGWOISBNVEC-UHFFFAOYSA-N
in ch i: InChI=1S/C20H23N5O/c1-12-7-14(10-22-9-12)17-11-23-19(24-15-3-5-21-6-4-15)18-16(17)8-13(2)20(26)25-18/h7-11,15,21H,3-6H2,1-2H3,(H,23,24)(H,25,26)
comment: Compound 57 is reported as a novel low-micromolar inhibitor of ATPase family, AAA domain containing 2 (ATAD2) <Reference id=28844/>. This compound has little selectivity over other BET domains tested so further optimisation would be required to optimise selectivity profile. ATAD2 inhibitors are being investigated for their potential anti-cancer effects.
iupac name: 3-methyl-5-(5-methylpyridin-3-yl)-8-[(piperidin-4-yl)amino]-1,2-dihydro-1,7-naphthyridin-2-one
approved: f
ligand name: compound 57 [PMID: 26155854]
type: SyntheticOrganicLigand

L-azetidine-2-carboxylate
canonical SMILES: OC(=O)C1CCN1
isomeric SMILES: OC(=O)[C@@H]1CCN1
in ch i key: IADUEWIQBXOCDZ-VKHMYHEASA-N
in ch i: InChI=1S/C4H7NO2/c6-4(7)3-1-2-5-3/h3,5H,1-2H2,(H,6,7)/t3-/m0/s1
comment: Amino acid homologue of proline found in plants
iupac name: (2S)-azetidine-2-carboxylic acid
xref: CHEMBL1165239
approved: f
ligand name: L-azetidine-2-carboxylate
type: NaturalProductLigand

compound 7r [PMID: 26080733]
in ch i key: ANMVTYAYYHHSTF-UHFFFAOYSA-N
in ch i: InChI=1S/C27H28FN5O2/c1-3-32-13-15-33(16-14-32)20-10-7-18(8-11-20)27(34)29-26-22-12-9-19(17-23(22)30-31-26)21-5-4-6-24(35-2)25(21)28/h4-12,17H,3,13-16H2,1-2H3,(H2,29,30,31,34)
comment: Compound 7r was designed using scaffold hopping and molecular hybridization strategies to identify novel FGFR inhibitors, based on the structures of existing FGFR inhibitors <Ligand id=7707/> and <Ligand id=7877/> <Reference id=28834/>. The X-ray structure of FGFR1 in complex with compound 7n (identical to 7r but without the 2-fluoro side group) has been reported and has RCSB Protein Data Bank ID 4ZSA <Reference id=28834/>.
iupac name: 4-(4-ethylpiperazin-1-yl)-N-[6-(2-fluoro-3-methoxyphenyl)-1H-indazol-3-yl]benzamide
approved: f
ligand name: compound 7r [PMID: 26080733]
type: SyntheticOrganicLigand

galeterone
in ch i key: PAFKTGFSEFKSQG-PAASFTFBSA-N
in ch i: InChI=1S/C26H32N2O/c1-25-13-11-18(29)15-17(25)7-8-19-20-9-10-24(26(20,2)14-12-21(19)25)28-16-27-22-5-3-4-6-23(22)28/h3-7,10,16,18-21,29H,8-9,11-15H2,1-2H3/t18-,19-,20-,21-,25-,26-/m0/s1
iupac name: (3S,8R,9S,10R,13S,14S)-17-(benzimidazol-1-yl)-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15-decahydro-1H-cyclopenta[a]phenanthren-3-ol
xref: CHEMBL2105738
synonym: TOK-001
synonym: VN/124-1
approved: f
ligand name: galeterone
type: SyntheticOrganicLigand

AK198
canonical SMILES: OC(=O)COc1cc(Cl)ccc1C(=O)NCc1ccc(cc1F)N
isomeric SMILES: OC(=O)COc1cc(Cl)ccc1C(=O)NCc1ccc(cc1F)N
in ch i key: GFJYPJDGRCZNDI-UHFFFAOYSA-N
comment: AK198 is an aldose reductase probe compound <Reference id=28831/>.
iupac name: 2-[2-[(4-amino-2-fluorophenyl)methylcarbamoyl]-5-chlorophenoxy]acetic acid
approved: f
ligand name: AK198
type: SyntheticOrganicLigand

compound 15 [PMID: 22017539]
in ch i key: MMJPVSDTLGFIQW-UHFFFAOYSA-N
in ch i: InChI=1S/C24H22N4O5/c1-3-33-24(32)20-11-17-10-16(8-9-18(17)26-20)21-12-19(27-28(21)2)22(29)25-13-14-4-6-15(7-5-14)23(30)31/h4-12,26H,3,13H2,1-2H3,(H,25,29)(H,30,31)
comment: Potent and selective MMP-13 inhibitor for possible treatment of arthritis
iupac name: 4-[[[5-(2-ethoxycarbonyl-1H-indol-5-yl)-1-methylpyrazole-3-carbonyl]amino]methyl]benzoic acid
xref: CHEMBL1939876
synonym: 4UF
approved: f
ligand name: compound 15 [PMID: 22017539]
type: SyntheticOrganicLigand

casp 4 inhib
canonical SMILES: O=C1N(C)c2c(C1=O)cc(cc2)[N+](=O)[O-]
isomeric SMILES: O=C1N(C)c2c(C1=O)cc(cc2)[N+](=O)[O-]
in ch i key: JPTDPTOWOMFBRY-UHFFFAOYSA-N
in ch i: InChI=1S/C9H6N2O4/c1-10-7-3-2-5(11(14)15)4-6(7)8(12)9(10)13/h2-4H,1H3
xref: CHEMBL293622
synonym: 5-nitro-isatin 1 [PMID: 11384246]
synonym: 1-methyl-5-nitro-isatin
approved: f
ligand name: casp 4 inhib
type: SyntheticOrganicLigand

compound 3 [PMID: 8410973]
in ch i key: MQDDTALXSBQTQP-DTXPUJKBSA-N
comment: Compound 3 is reported to inhibit human pepsin, in addition to gastricsin and cathepsins D and E <Reference id=22305/>.
iupac name: (4S)-5-cyclohexyl-2,2-difluoro-N-(2-morpholin-4-ylethyl)-4-[[(2S)-2-[[(2S)-2-(morpholin-4-ylsulfonylamino)-3-phenylpropanoyl]amino]pent-4-enoyl]amino]-3-oxopentanamide
xref: CHEMBL287423
approved: f
ligand name: compound 3 [PMID: 8410973]
type: SyntheticOrganicLigand

compound 7u [PMID: 24775305]
in ch i key: BZVXYJWEOARYIS-UNMCSNQZSA-N
in ch i: InChI=1S/C25H28N4O5/c1-2-33-21-6-3-5-19(13-21)18-10-8-17(9-11-18)16-34-25(32)29-12-4-7-22(29)24(31)28-20(15-26)14-23(27)30/h3,5-6,8-11,13,20,22H,2,4,7,12,14,16H2,1H3,(H2,27,30)(H,28,31)/t20-,22-/m0/s1
comment: Compound 7u is reported to inhibit the asparaginyl endopeptidase, legumain <Reference id=28822/>.
iupac name: [4-(3-ethoxyphenyl)phenyl]methyl (2S)-2-[[(1S)-3-amino-1-cyano-3-oxopropyl]carbamoyl]pyrrolidine-1-carboxylate
xref: CHEMBL3264590
approved: f
ligand name: compound 7u [PMID: 24775305]
type: SyntheticOrganicLigand

compound 6 [PMID: 10395480]
in ch i key: PDGQBIYMLALKTR-FIQHERPVSA-N
in ch i: InChI=1S/C15H28N4O4/c1-8(2)7-10(16)12(20)15(23)19-6-4-5-11(19)14(22)18-9(3)13(17)21/h8-12,20H,4-7,16H2,1-3H3,(H2,17,21)(H,18,22)/t9-,10-,11-,12+/m0/s1
comment: Compound 6 is reported as an inhibitor of membrane-bound aminopeptidase P (XPNPEP1 and XPNPEP2) <Reference id=28821/>. XPNPEP inhibitors would be expected to reduce the degradation of bradykinin, with resulting anti-hypertensive effects.
iupac name: (2S)-1-[(2R,3S)-3-amino-2-hydroxy-5-methylhexanoyl]-N-[(2S)-1-amino-1-oxopropan-2-yl]pyrrolidine-2-carboxamide
xref: CHEMBL2369858
approved: f
ligand name: compound 6 [PMID: 10395480]
type: SyntheticOrganicLigand

compound 40 [PMID: 10602705]
in ch i key: HUWSZNZAROKDRZ-RRLWZMAJSA-N
in ch i: InChI=1S/C17H29N3O9S2/c1-3-8(2)11(19-14(21)13(30)10(18)5-7-31(27,28)29)15(22)20-6-4-9(16(23)24)12(20)17(25)26/h8-13,30H,3-7,18H2,1-2H3,(H,19,21)(H,23,24)(H,25,26)(H,27,28,29)/t8-,9?,10-,11+,12+,13-/m1/s1
comment: Compound 40 is reported as an inhibitor of glutamyl aminopeptidase (ENPEP) <Reference id=28748/>.
iupac name: (2S)-1-[(2S,3R)-2-[[(2R,3R)-3-amino-2-sulfanyl-5-sulfopentanoyl]amino]-3-methylpentanoyl]pyrrolidine-2,3-dicarboxylic acid
xref: CHEMBL146746
synonym: H(3)N(+)CH(CH(2)CH(2)SO(3)(-))CH(SH)CO-Ile-(3-COOH)Pro
approved: f
ligand name: compound 40 [PMID: 10602705]
type: SyntheticOrganicLigand

SL422
in ch i key: HFAGTNGCAZYYLZ-OTWHNJEPSA-N
in ch i: InChI=1S/C23H34N4O6/c1-14(2)11-18-17(22(30)27-32)5-4-10-33-16-8-6-15(7-9-16)12-19(26-21(18)29)23(31)25-13-20(28)24-3/h6-9,14,17-19,32H,4-5,10-13H2,1-3H3,(H,24,28)(H,25,31)(H,26,29)(H,27,30)/t17-,18+,19-/m0/s1
comment: SL422 was identified using a structure-activity aided strategy to identify novel small molecule inhibitors of ADAM17, the tumor necrosis factor, alpha, converting enzyme (TACE) <Reference id=28745/>.
xref: CHEMBL88520
synonym: analogue 55f [PMID: 11472217]
approved: f
ligand name: SL422
type: SyntheticOrganicLigand

compound 4 [PMID: 12408711]
in ch i key: MENAYYMPBRSAAE-AWEZNQCLSA-N
in ch i: InChI=1S/C18H17N3O8S/c22-10-14(7-16(23)24)21-17(25)12-4-5-13(19-8-12)9-20-30(28,29)15-3-1-2-11(6-15)18(26)27/h1-6,8,10,14,20H,7,9H2,(H,21,25)(H,23,24)(H,26,27)/t14-/m0/s1
comment: Compound 4 was identified using a structure-activity based approach to identify novel caspase 3 inhibitors <Reference id=28744/>.
iupac name: 5-[[5-[[(2S)-1-carboxy-3-oxopropan-2-yl]carbamoyl]pyridin-2-yl]methylsulfamoyl]-2-hydroxybenzoic acid
xref: CHEMBL358725
approved: f
ligand name: compound 4 [PMID: 12408711]
type: SyntheticOrganicLigand

compound 1b [PMID: 18078750]
in ch i key: BNECOBGISSOLPT-FCHUYYIVSA-N
in ch i: InChI=1S/C24H23NO3S/c26-23(22(29)16-17-7-3-1-4-8-17)25-21(24(27)28)15-18-11-13-20(14-12-18)19-9-5-2-6-10-19/h1-14,21-22,29H,15-16H2,(H,25,26)(H,27,28)/t21-,22+/m0/s1
comment: Compound 1b was synthesised in a medicinal chemisrty study aiming to discover novel angiotensin-converting enzyme 2 inhibitors (ACE2) <Reference id=28743/>.
iupac name: (2S)-3-(4-phenylphenyl)-2-[[(2R)-3-phenyl-2-sulfanylpropanoyl]amino]propanoic acid
xref: CHEMBL163454
approved: f
ligand name: compound 1b [PMID: 18078750]
type: SyntheticOrganicLigand

compound 4g [PMID: 22595175]
canonical SMILES: COc1ccc(cc1)C(=O)N1C(=O)OC(C1=O)(C)C
isomeric SMILES: COc1ccc(cc1)C(=O)N1C(=O)OC(C1=O)(C)C
in ch i key: ZYRNCIWULACSEK-UHFFFAOYSA-N
in ch i: InChI=1S/C13H13NO5/c1-13(2)11(16)14(12(17)19-13)10(15)8-4-6-9(18-3)7-5-8/h4-7H,1-3H3
comment: Compound 4g is reported as an inhibitor of proteinase 3 <Reference id=28742/>.
iupac name: 3-(4-methoxybenzoyl)-5,5-dimethyl-1,3-oxazolidine-2,4-dione
xref: CHEMBL2029556
approved: f
ligand name: compound 4g [PMID: 22595175]
type: SyntheticOrganicLigand

o-F-amidine
in ch i key: HBEIARVCIYYMOR-UHFFFAOYSA-N
in ch i: InChI=1S/C15H19FN4O4/c16-8-12(17)19-7-3-6-11(13(18)21)20-14(22)9-4-1-2-5-10(9)15(23)24/h1-2,4-5,11H,3,6-8H2,(H2,17,19)(H2,18,21)(H,20,22)(H,23,24)
comment: This compound is an irreversible inhibitor of protein arginine deiminases, with selectivity for PADI1 and PADI4 <Reference id=29097/>. It can be used to study protein arginine deiminase function. Our structure was drawn from <Reference id=29097/>. PubChem CID 54669783 represents an alternative tautomer, and both CHEMBL1962643 and the PDB ligand (YFF&sid=3B1U) have defined stereochemistry which we don't include.
synonym: compound 17 [PMID: 21882827]
approved: f
ligand name: o-F-amidine
type: SyntheticOrganicLigand

3S,4R-293B
canonical SMILES: CCS(=O)(=O)N(C1C(O)C(C)(C)Oc2c1cc(cc2)C#N)C
in ch i key: HVSJHHXUORMCGK-KGLIPLIRSA-N
in ch i: InChI=1S/C15H20N2O4S/c1-5-22(19,20)17(4)13-11-8-10(9-16)6-7-12(11)21-15(2,3)14(13)18/h6-8,13-14,18H,5H2,1-4H3/t13-,14+/m1/s1
comment: This is an alternative enantiomer of <Ligand id=2589/>. The stereo-specific effects of this ligand and the <Ligand id=2589/> enantiomer has been reported by Seebohm et al. (2001) <Reference id=28720/>. Note that some biological activity data may have been generated using the racemic mixture (chromanol 239B) represented by the 'flat' structure with PubChem CID 656731. Additional partially specified stereo-isomers include CID 44275282 and CID 44275281.
iupac name: N-[(3S,4R)-6-cyano-3-hydroxy-2,2-dimethyl-3,4-dihydrochromen-4-yl]-N-methylethanesulfonamide
xref: CHEMBL44297
synonym: chromanol 239B
approved: f
ligand name: 3S,4R-293B
type: SyntheticOrganicLigand

[14C]glycine
canonical SMILES: NCC(=O)O
isomeric SMILES: NCC(=O)O
in ch i key: DHMQDGOQFOQNFH-UHFFFAOYSA-N
in ch i: InChI=1S/C2H5NO2/c3-1-2(4)5/h1,3H2,(H,4,5)
iupac name: 2-aminoacetic acid
xref: CHEMBL773
synonym: [14C]-glycine
approved: f
ligand name: [14C]glycine
type: SyntheticOrganicLigand

inhibitor 1 [Colombo et al., 2012]
in ch i key: JRNGHBUUFQDBPT-LAQRGFTBSA-N
in ch i: InChI=1S/C27H42N12O5S/c1-14(36-24(44)18(10-11-20(29)40)38-23(43)15(28)6-4-12-34-26(30)31)22(42)37-17(8-5-13-35-27(32)33)21(41)25-39-16-7-2-3-9-19(16)45-25/h2-3,7,9,14-15,17-18H,4-6,8,10-13,28H2,1H3,(H2,29,40)(H,36,44)(H,37,42)(H,38,43)(H4,30,31,34)(H4,32,33,35)/t14-,15-,17-,18-/m0/s1
comment: Inhibitor 1 is a peptidomimetic inhibitor of matriptase enzymes, based on the P4−P1 (Arg-Gln-Ala-Arg) portion of the activation peptide of matriptase <Reference id=28741/>.
xref: CHEMBL2086421
approved: f
ligand name: inhibitor 1 [Colombo et al., 2012]
type: SyntheticOrganicLigand

compound 4 [PMID: 19954973]
canonical SMILES: NCCOC(C(=O)O)Cc1ncn(c1)c1ccccc1
isomeric SMILES: NCCO[C@H](C(=O)O)Cc1ncn(c1)c1ccccc1
in ch i key: LVCATUGNENEDGZ-ZDUSSCGKSA-N
in ch i: InChI=1S/C14H17N3O3/c15-6-7-20-13(14(18)19)8-11-9-17(10-16-11)12-4-2-1-3-5-12/h1-5,9-10,13H,6-8,15H2,(H,18,19)/t13-/m0/s1
comment: Compound 4 is reported to inhibit the activatable fibrinolysis inhibitor, plasma carboxypeptidase B2 (CPB2) <Reference id=28740/>. Inhibitors of CBP2 have been investigated as novel treatments for thrombosis.
iupac name: (2S)-2-(2-aminoethoxy)-3-(1-phenylimidazol-4-yl)propanoic acid
xref: CHEMBL589645
approved: f
ligand name: compound 4 [PMID: 19954973]
type: SyntheticOrganicLigand

compound 3d [PMID: 3941405]
canonical SMILES: NCC(=O)NC(Cc1ccccc1)C#N
isomeric SMILES: NCC(=O)NC(Cc1ccccc1)C#N
in ch i key: QLVGHFBUSGYCCG-UHFFFAOYSA-N
in ch i: InChI=1S/C11H13N3O/c12-7-10(14-11(15)8-13)6-9-4-2-1-3-5-9/h1-5,10H,6,8,13H2,(H,14,15)
comment: Compound 3d is reported to inhibit dipeptidyl peptidase I (aka cathepsin C) <Reference id=28739/>.
iupac name: 2-amino-N-(1-cyano-2-phenylethyl)acetamide
xref: CHEMBL12954
approved: f
ligand name: compound 3d [PMID: 3941405]
type: SyntheticOrganicLigand

JZL195
in ch i key: QNYRAEKLMNDRFY-UHFFFAOYSA-N
in ch i: InChI=1S/C24H23N3O5/c28-24(32-22-11-9-20(10-12-22)27(29)30)26-15-13-25(14-16-26)18-19-5-4-8-23(17-19)31-21-6-2-1-3-7-21/h1-12,17H,13-16,18H2
comment: JZL195 was first reported as a dual inhibitor of fatty acid amide hydrolase (FAAH) and monoacylglycerol lipase (MGLL, a.k.a. MAGL) in 2009 <Reference id=30462/>. Animal experiments suggest that dual FAAH/MAGL inhibitiors may have improved analgesic effects against neuropathic pain, in comparison to selective FAAH and MAGL inhibitors, or cannabinoid receptor agonists <Reference id=30463/><Reference id=30464/><Reference id=30465/><Reference id=30470/>. JZL195 has since been reported to also inhibit acyloxyacyl hydrolase (AOAH) <Reference id=28714/>
iupac name: (4-nitrophenyl) 4-[(3-phenoxyphenyl)methyl]piperazine-1-carboxylate
xref: CHEMBL606201
synonym: JZL-195
synonym: JZL 195
approved: f
ligand name: JZL195
type: SyntheticOrganicLigand

inhibitor 19 [PMID: 21476495]
in ch i key: QUJXIMWUJGTUEG-CLKUPZDLSA-N
in ch i: InChI=1S/C29H36N4O6/c30-24-9-3-1-2-4-10-25(29(39)31-18-21-8-6-5-7-20(21)16-27(36)37)33-26(35)17-22(32-28(24)38)15-19-11-13-23(34)14-12-19/h1-2,5-8,11-14,22,24-25,34H,3-4,9-10,15-18,30H2,(H,31,39)(H,32,38)(H,33,35)(H,36,37)/b2-1+/t22-,24-,25-/m0/s1
comment: Inhibitor 19 is a macrocyclic analogue of angiotensin IV (AT4) reported to potently inhibit leucyl/cystinyl aminopeptidase (LNPEP) <Reference id=28733/>. LNPEP (IRAP) inhibitors are being investigated as potential therapeutics utilising a novel mechanism to treat memory dysfunction <Reference id=28734/><Reference id=28735/><Reference id=28736/>.
iupac name: 2-[2-[[[(2S,6S,9E,13S)-13-amino-2-[(4-hydroxyphenyl)methyl]-4,14-dioxo-1,5-diazacyclotetradec-9-ene-6-carbonyl]amino]methyl]phenyl]acetic acid
xref: CHEMBL1782887
approved: f
ligand name: inhibitor 19 [PMID: 21476495]
type: SyntheticOrganicLigand

S136492
canonical SMILES: O=C1C=CC=CC1=CC=c1ccc2c([nH]1)cccc2
isomeric SMILES: O=C1C=CC=C/C/1=C/C=c/1/ccc2c([nH]1)cccc2
in ch i key: YWORVGQOCNQBFI-VDQVFBMKSA-N
in ch i: InChI=1S/C17H13NO/c19-17-8-4-2-6-14(17)10-12-15-11-9-13-5-1-3-7-16(13)18-15/h1-12,18H/b14-10+,15-12+
comment: ECE-2 inhibitor. Unlike ECE-1, this protease has a restricted neuroendocrine distribution, an acidic pH optimum and may regulate neuropeptide levels <Reference id=28731/>. Note there are a number of tautomeric forms in PubChem that vary in the double bond renderings. Note the publication that introduces the name S136492 <Reference id=28732/> does not make the structure explicit but refers to the earlier paper <Reference id=28731/>.
iupac name: (6E)-6-[(2E)-2-(1H-quinolin-2-ylidene)ethylidene]cyclohexa-2,4-dien-1-one
synonym: Cpd 3 (PMID 24990314)
approved: f
ligand name: S136492
type: SyntheticOrganicLigand

compound 28 [PMID: 16460935]
in ch i key: HEZXZGJJNMPIJM-UHFFFAOYSA-N
comment: Compound 28 is reported to inhibit complement component 1, s subcomponent (C1S), with excellent selectivity over uPA (urokinase plasminogen activator) and good selectivity over tPA (tissue plasminogen activator), FXa, thrombin, and plasmin <Reference id=28730/>.
iupac name: 4-[7-bromo-1-[(2,5-difluorophenyl)methyl]benzimidazol-5-yl]sulfonyl-5-methylsulfanylthiophene-2-carboximidamide
xref: CHEMBL205904
approved: f
ligand name: compound 28 [PMID: 16460935]
type: SyntheticOrganicLigand

compound 3b [PMID: 24946214]
in ch i key: QCKLWTRAVKQTPI-HNNXBMFYSA-N
in ch i: InChI=1S/C17H23BN2O4/c1-12(2)11-15(18(23)24)19-16(21)8-10-20-9-7-13-5-3-4-6-14(13)17(20)22/h3-7,9,12,15,23-24H,8,10-11H2,1-2H3,(H,19,21)/t15-/m0/s1
comment: Compound 3b <Reference id=28729/> is reported to inhibit the chymotrypsin-like (ChT-L) and post-glutamyl peptide hydrolyzing (PGHP) activities of the 20S proteasome <Reference id=28729/>.
iupac name: [(1R)-3-methyl-1-[3-(1-oxoisoquinolin-2-yl)propanoylamino]butyl]boronic acid
xref: CHEMBL3287940
approved: f
ligand name: compound 3b [PMID: 24946214]
type: SyntheticOrganicLigand

PD159790
in ch i key: IRWWFCJIOHCTMV-UHFFFAOYSA-N
in ch i: InChI=1S/C16H18F3IN4/c1-2-24-7-3-4-11(9-24)21-14-12-8-10(20)5-6-13(12)22-15(23-14)16(17,18)19/h5-6,8,11H,2-4,7,9H2,1H3,(H,21,22,23)
comment: ECE-1 selective inhibitor <Reference id=28727/>
iupac name: N-(1-ethylpiperidin-3-yl)-6-iodo-2-(trifluoromethyl)quinazolin-4-amine
synonym: PD-159790
approved: f
ligand name: PD159790
type: SyntheticOrganicLigand

MG-132
in ch i key: TZYWCYJVHRLUCT-VABKMULXSA-N
in ch i: InChI=1S/C26H41N3O5/c1-17(2)12-21(15-30)27-24(31)22(13-18(3)4)28-25(32)23(14-19(5)6)29-26(33)34-16-20-10-8-7-9-11-20/h7-11,15,17-19,21-23H,12-14,16H2,1-6H3,(H,27,31)(H,28,32)(H,29,33)/t21-,22-,23-/m0/s1
comment: Compound 5b is reported to inhibit the enzymatic activity of proteasome macropain <Reference id=28725/>.
iupac name: phenylmethyl N-[(2S)-4-methyl-1-[[(2S)-4-methyl-1-[[(2S)-4-methyl-1-oxopentan-2-yl]amino]-1-oxopentan-2-yl]amino]-1-oxopentan-2-yl]carbamate
xref: CHEMBL64925
synonym: MG132
synonym: MG 132
synonym: Z-Leu-leu-leu-al
synonym: Z-LLL-CHO
synonym: compound 5b [PMID: 16686537]
synonym: N-benzyloxycarbonyl-L-leucyl-L-leucyl-L-leucinal
approved: f
ligand name: MG-132
type: PeptideLigand

compound 5a [PMID: 20690647]
in ch i key: OVLNPOAZKHQAAD-BBMPLOMVSA-N
in ch i: InChI=1S/C32H38N8O5/c1-21(2)16-25(39-32(44)45-18-23-12-7-4-8-13-23)30(42)38-24(17-22-10-5-3-6-11-22)27(41)31(43)34-14-9-15-40-20-37-26-28(33)35-19-36-29(26)40/h3-8,10-13,19-21,24-25H,9,14-18H2,1-2H3,(H,34,43)(H,38,42)(H,39,44)(H2,33,35,36)/t24?,25-/m0/s1
comment: Compound 5a is reported as an inhibitor of calpain 2 <Reference id=28724/>.
iupac name: benzyl N-[(2S)-1-[[4-[3-(6-aminopurin-9-yl)propylamino]-3,4-dioxo-1-phenylbutan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]carbamate
xref: CHEMBL1240872
synonym: Cbz-Leu-D,L-Phe-CONH-(CH(2))(3)-adenin-9-yl
approved: f
ligand name: compound 5a [PMID: 20690647]
type: SyntheticOrganicLigand

compound 4b [PMID: 20690647]
in ch i key: MBPXUEHDROHPFW-ANYOKISRSA-N
in ch i: InChI=1S/C28H38N8O6/c1-5-19(32-25(38)20(14-17(2)3)33-28(40)42-15-18-10-7-6-8-11-18)22(37)26(39)30-12-9-13-36-16-31-21-23(29)34-27(41-4)35-24(21)36/h6-8,10-11,16-17,19-20H,5,9,12-15H2,1-4H3,(H,30,39)(H,32,38)(H,33,40)(H2,29,34,35)/t19?,20-/m0/s1
comment: Compound 4b is reported as an inhibitor of calpain 1 <Reference id=28724/>.
iupac name: benzyl N-[(2S)-1-[[1-[3-(6-amino-2-methoxypurin-9-yl)propylamino]-1,2-dioxopentan-3-yl]amino]-4-methyl-1-oxopentan-2-yl]carbamate
xref: CHEMBL1240873
synonym: Cbz-Leu-D,L-Abu-CONH-(CH(2))(3)-2-methoxyadenin-9-yl
approved: f
ligand name: compound 4b [PMID: 20690647]
type: SyntheticOrganicLigand

compound 1b [PMID: 16290936]
canonical SMILES: CCCCC(NC(=O)OC(Cc1ccccc1)C)C=O
isomeric SMILES: CCCC[C@H](NC(=O)O[C@H](Cc1ccccc1)C)C=O
in ch i key: WNKGMQLRHKONID-ZFWWWQNUSA-N
in ch i: InChI=1S/C16H23NO3/c1-3-4-10-15(12-18)17-16(19)20-13(2)11-14-8-6-5-7-9-14/h5-9,12-13,15H,3-4,10-11H2,1-2H3,(H,17,19)/t13-,15-/m0/s1
comment: Compound 1b is reported primarily as an inhibitor of cathepsin K, but also substantially inhibits cathepsin H <Reference id=28723/>.
iupac name: [(2S)-1-phenylpropan-2-yl] N-[(2S)-1-oxohexan-2-yl]carbamate
xref: CHEMBL114161
approved: f
ligand name: compound 1b [PMID: 16290936]
type: SyntheticOrganicLigand

compound 37 [PMID: 24418773]
in ch i key: CHAFCBBAYJKFNL-RPWUZVMVSA-N
in ch i: InChI=1S/C28H38N6O4/c29-22-12-8-19(9-13-22)15-24(27(37)33-16-20-6-10-21(11-7-20)26(30)31)34-28(38)23(32-17-25(35)36)14-18-4-2-1-3-5-18/h6-13,18,23-24,32H,1-5,14-17,29H2,(H3,30,31)(H,33,37)(H,34,38)(H,35,36)/t23-,24+/m1/s1
comment: Compound 37 is a small molecule inhibitor of activated protein C <Reference id=28721/>.
iupac name: 2-[[(2R)-1-[[(2S)-3-(4-aminophenyl)-1-[(4-carbamimidoylphenyl)methylamino]-1-oxopropan-2-yl]amino]-3-cyclohexyl-1-oxopropan-2-yl]amino]acetic acid
xref: CHEMBL3115901
approved: f
ligand name: compound 37 [PMID: 24418773]
type: SyntheticOrganicLigand

Deuterium-substituted L-DOPA
canonical SMILES: OC(=O)C(Cc1ccc(c(c1)O)O)N
in ch i key: WTDRDQBEARUVNC-QZRTVAIESA-N
in ch i: InChI=1S/C9H11NO4/c10-6(9(13)14)3-5-1-2-7(11)8(12)4-5/h1-2,4,6,11-12H,3,10H2,(H,13,14)/t6-/m0/s1/i3D2,6D
comment: Chronic treatment with a substantially lower dose of deuterium-substituted L-DOPA (D3-L-DOPA), compared with L-DOPA (<Ligand id=3639/>) produced equal anti-parkinsonian effects and reduced dyskinesia in 6-OHDA-lesioned rats <Reference id=28726/>. This new rat study reports similar effect produced by D3-L-DOPA and selegiline plus L-DOPA, respectively, implying adjuvant MAO-B inhibitor treatment may not be necessary with D3-L-DOPA <Reference id=28722/>. This compound was proposed for development by the Michael J Fox foundation but there is no ClinicalTrials.gov entry.
iupac name: (2S)-2-amino-2,3,3-trideuterio-3-(3,4-dihydroxyphenyl)propanoic acid
synonym: Deuterium-substituted L-DOPA
synonym: DP-102
approved: f
ligand name: Deuterium-substituted L-DOPA
type: SyntheticOrganicLigand

KL044
in ch i key: ZDAKKNHUWVTCRS-UHFFFAOYSA-N
in ch i: InChI=1S/C21H14ClN3O/c22-17-9-5-6-14(12-23)21(17)24-20(26)13-25-18-10-3-1-7-15(18)16-8-2-4-11-19(16)25/h1-11H,13H2,(H,24,26)
comment: KL044 is reported to lengthen the photoperiod by binding to and stabilising mammalian CRY1 <Reference id=28719/>.
iupac name: 2-(9H-carbazol-9-yl)-N-(2-chloro-6-cyanophenyl)acetamide
synonym: KL 044
synonym: KL-044
approved: f
ligand name: KL044
type: SyntheticOrganicLigand

ABL127
in ch i key: ZRHWCAFAIHTQKD-KRWDZBQOSA-N
in ch i: InChI=1S/C17H20N2O5/c1-23-15(21)18-14(20)17(13-10-6-7-11-13,19(18)16(22)24-2)12-8-4-3-5-9-12/h3-5,8-9,13H,6-7,10-11H2,1-2H3/t17-/m0/s1
comment: ABL127 is reported to inhibit protein phosphatase methylesterase 1 (PPME1) <Reference id=28714/>.
iupac name: dimethyl (3R)-3-cyclopentyl-4-oxo-3-phenyldiazetidine-1,2-dicarboxylate
xref: CHEMBL1475741
synonym: ABL-127
synonym: ABL 127
approved: f
ligand name: ABL127
type: SyntheticOrganicLigand

Ala(1-naph)-Pro-CN
canonical SMILES: N#CC1CCCN1C(=O)C(Cc1cccc2c1cccc2)N
in ch i key: ZVRWNKCHASBEDZ-RDJZCZTQSA-N
in ch i: InChI=1S/C18H19N3O/c19-12-15-8-4-10-21(15)18(22)17(20)11-14-7-3-6-13-5-1-2-9-16(13)14/h1-3,5-7,9,15,17H,4,8,10-11,20H2/t15-,17-/m0/s1
comment: Ala(1-naph)-Pro-CN is reported to inhibit the putative hydrolase RBBP9 and dipeptidyl-peptidase 4 (DPP4) <Reference id=28714/>.
iupac name: (2S)-1-[(2S)-2-amino-3-naphthalen-1-ylpropanoyl]pyrrolidine-2-carbonitrile
approved: f
ligand name: Ala(1-naph)-Pro-CN
type: SyntheticOrganicLigand

tideglusib
canonical SMILES: O=c1sn(c(=O)n1Cc1ccccc1)c1cccc2c1cccc2
isomeric SMILES: O=c1sn(c(=O)n1Cc1ccccc1)c1cccc2c1cccc2
in ch i key: PMJIHLSCWIDGMD-UHFFFAOYSA-N
in ch i: InChI=1S/C19H14N2O2S/c22-18-20(13-14-7-2-1-3-8-14)19(23)24-21(18)17-12-6-10-15-9-4-5-11-16(15)17/h1-12H,13H2
comment: Tideglusib is a small molecule non-ATP-competitive, irreversible glycogen synthase kinase 3 (GSK-3β) inhibitor <Reference id=23477/> that has been investigated as a potential treatment for Alzheimer's disease and paralysis supranuclear palsy <Reference id=23475/>. Low-dose tideglusib has been reported to induce natural reparative dentine formation, as a novel approach to treating tooth decay <Reference id=31917/>. In vitro and in vivo, tideglusib (and analogues) has shown anti-staphylococcal activity, via inhibition of Staphylococcus aureus sortase A (SrtA; a virulence factor of Gram-positive pathogens) <Reference id=39937/>.
iupac name: 4-benzyl-2-(naphthalen-1-yl)-1,2,4-thiadiazolidine-3,5-dione
synonym: NP031112
approved: f
ligand name: tideglusib
type: SyntheticOrganicLigand

GSK2194069
in ch i key: AQTPWCUIYUOEMG-INIZCTEOSA-N
in ch i: InChI=1S/C25H24N4O3/c30-24(18-1-2-18)28-11-9-16(15-28)13-23-26-27-25(31)29(23)21-6-3-17(4-7-21)19-5-8-22-20(14-19)10-12-32-22/h3-8,10,12,14,16,18H,1-2,9,11,13,15H2,(H,27,31)/t16-/m0/s1
comment: GSK2194069 is reported to selectively and potently inhibit fatty acid synthase (FASN) <Reference id=28712/>.
iupac name: 4-[4-(1-benzofuran-5-yl)phenyl]-3-[[(3S)-1-(cyclopropanecarbonyl)pyrrolidin-3-yl]methyl]-1H-1,2,4-triazol-5-one
synonym: GSK-2194069
synonym: GSK 2194069
approved: f
ligand name: GSK2194069
type: SyntheticOrganicLigand

BODIPY-pirenzepine
in ch i key: QGXCAYBSIKPOHP-ORIPQNMZSA-N
comment: Fluorescence-labelled probe that binds to enhanced green fluorescent protein (EGFP)-fused muscarinic M1 receptors in living cells and facilitates real time monitoring <Reference id=28711/>.
iupac name: 3-[1-difluoroboranyl-5-[(E)-(5-thiophen-2-ylpyrrol-2-ylidene)methyl]pyrrol-2-yl]-N-[6-[4-[2-oxo-2-(6-oxo-5H-pyrido[2,3-b][1,4]benzodiazepin-11-yl)ethyl]piperazin-1-yl]hexyl]propanamide
synonym: Bodipy[558/568]Pirenzepine
synonym: BoPz
approved: f
ligand name: BODIPY-pirenzepine
type: SyntheticOrganicLigand

compound 10l [PMID: 24556381]
in ch i key: LQGHUZLZFHCQPO-UHFFFAOYSA-N
in ch i: InChI=1S/C23H15N3O2/c27-26(28)16-10-11-22-19(12-16)18(15-6-2-1-3-7-15)13-23(25-22)20-14-24-21-9-5-4-8-17(20)21/h1-14,24H
comment: Compound 10l is reported to inhibit neutrophil elastase and carboxyl ester lipase (aka cholesterol esterase) <Reference id=28710/>.
iupac name: 2-(1H-indol-3-yl)-6-nitro-4-phenylquinoline
xref: CHEMBL3125351
approved: f
ligand name: compound 10l [PMID: 24556381]
type: SyntheticOrganicLigand

compound 10f [PMID: 24556381]
in ch i key: LTUZPODERZUPRD-UHFFFAOYSA-N
in ch i: InChI=1S/C23H15ClN2/c24-16-10-11-22-19(12-16)18(15-6-2-1-3-7-15)13-23(26-22)20-14-25-21-9-5-4-8-17(20)21/h1-14,25H
comment: Compound 10f is reported to inhibit neutrophil elastase and carboxyl ester lipase (aka cholesterol esterase) <Reference id=28710/>.
iupac name: 6-chloro-2-(1H-indol-3-yl)-4-phenylquinoline
xref: CHEMBL3125346
approved: f
ligand name: compound 10f [PMID: 24556381]
type: SyntheticOrganicLigand

MI-1148
in ch i key: HXVPWVPTVOOCMV-UNCTUWKVSA-N
in ch i: InChI=1S/C36H57N15O4/c1-36(2,3)28(32(55)50-25(6-4-16-45-33(39)40)30(53)47-19-23-12-14-24(15-13-23)29(37)38)51-31(54)26(7-5-17-46-34(41)42)49-27(52)18-21-8-10-22(11-9-21)20-48-35(43)44/h8-15,25-26,28H,4-7,16-20H2,1-3H3,(H3,37,38)(H,47,53)(H,49,52)(H,50,55)(H,51,54)(H4,39,40,45)(H4,41,42,46)(H4,43,44,48)/t25-,26-,28+/m0/s1
comment: MI-1148 is reported as an inhibitor of furin <Reference id=28709/>, with potential as an anti-infective agent active against avian influenza and canine distemper viruses. MI-1148 is structurally related to <Ligand id=6564/>.
synonym: 4-guanidinomethyl-phenylacteyl-Arg-Tle-Arg-4-amidinobenzylamide
synonym: para-guanidinomethyl-Phac-R-Tle-R-Amba
approved: f
ligand name: MI-1148
type: SyntheticOrganicLigand

Alexa-488-telenzepine
in ch i key: SRLBGILQMKQWSJ-UHFFFAOYSA-H
comment: Fluorescence-labelled ligand.
approved: f
ligand name: Alexa-488-telenzepine
type: SyntheticOrganicLigand

quinoline 2
in ch i key: IRFHMTUHTBSEBK-QGZVFWFLSA-N
in ch i: InChI=1S/C23H24F2N2O2/c1-23(2,3)29-22(28)27-14-17(19-12-18(24)8-9-20(19)25)11-15-10-16-6-4-5-7-21(16)26-13-15/h4-10,12-13,17H,11,14H2,1-3H3,(H,27,28)/t17-/m1/s1
iupac name: tert-butyl N-[(2S)-2-(2,5-difluorophenyl)-3-quinolin-3-ylpropyl]carbamate
approved: f
ligand name: quinoline 2
type: SyntheticOrganicLigand

Cy3B-telenzepine
in ch i key: DGPHRPUJPHDIPO-UHFFFAOYSA-L
in ch i: InChI=1S/C59H73N7O7S2/c1-38-54-43(37-74-38)57(69)61-46-16-12-13-17-49(46)66(54)53(68)36-63-30-28-62(29-31-63)25-15-11-9-7-6-8-10-14-24-60-52(67)33-39-18-20-47-44(32-39)58(2,3)55-41-35-42-51(73-50(41)22-26-64(47)55)23-27-65-48-21-19-40(75(70,71)72)34-45(48)59(4,5)56(42)65/h12-13,16-21,32,34-35,37,50-51H,6-11,14-15,22-31,33,36H2,1-5H3,(H4-,60,61,67,69,70,71,72)/p-2
comment: A fluorescence-labelled ligand.
approved: f
ligand name: Cy3B-telenzepine
type: SyntheticOrganicLigand

NI-57
in ch i key: UEMQPCYDWCSVCU-UHFFFAOYSA-N
in ch i: InChI=1S/C19H17N3O4S/c1-12-8-14-10-15(5-6-16(14)22(2)19(12)23)21-27(24,25)18-7-4-13(11-20)9-17(18)26-3/h4-10,21H,1-3H3
comment: This compound from the Structural Genomics Consortium's (SGC) Epigenetics Probes Collection, is a useful tool for studying the function of bromodomains in BRPF1, -2 (HGNC gene symbol BRD1) and -3 proteins. BRPF1/2/3 provide the scaffold for the formation of MYST complexes which play essential functions in DNA repair, recombination, replication and activation of transcription.
iupac name: 4-cyano-N-(1,3-dimethyl-2-oxoquinolin-6-yl)-2-methoxybenzenesulfonamide
approved: f
ligand name: NI-57
type: SyntheticOrganicLigand

NTE-2
in ch i key: SDVPSGCYRLUZSS-WXSHXSFMSA-N
in ch i: InChI=1S/C44H54FN5O4/c1-54-44(53)48-29-35(26-32-25-34-15-8-9-17-40(34)47-28-32)37-27-31(20-23-38(37)45)12-5-2-4-11-30-18-21-36(22-19-30)49-42(51)41(33-13-6-3-7-14-33)50-24-10-16-39(46)43(50)52/h8-9,15,17-23,25,27-28,33,35,39,41H,2-7,10-14,16,24,26,29,46H2,1H3,(H,48,53)(H,49,51)/t35-,39+,41+/m1/s1
comment: NTE-2 is reported as an inhibitor of insulin-degrading enzyme (IDE) <Reference id=28707/>. The compound binds to an exosite, distinct from the active enzyme site.
iupac name: methyl N-[(2S)-2-[5-[5-[4-[[(2S)-2-[(3S)-3-amino-2-oxopiperidin-1-yl]-2-cyclohexylacetyl]amino]phenyl]pentyl]-2-fluorophenyl]-3-quinolin-3-ylpropyl]carbamate
approved: f
ligand name: NTE-2
type: SyntheticOrganicLigand

NTE-1
in ch i key: IGRIVAWLJUPVMM-UDEWTJCRSA-N
in ch i: InChI=1S/C44H55N5O5/c1-53-44(52)47-30-36(28-32-27-35-14-7-8-16-40(35)46-29-32)33-19-23-38(24-20-33)54-26-9-3-4-11-31-17-21-37(22-18-31)48-42(50)41(34-12-5-2-6-13-34)49-25-10-15-39(45)43(49)51/h7-8,14,16-24,27,29,34,36,39,41H,2-6,9-13,15,25-26,28,30,45H2,1H3,(H,47,52)(H,48,50)/t36-,39+,41+/m1/s1
comment: NTE-1 is reported as an inhibitor of insulin-degrading enzyme (IDE) <Reference id=28707/>. The compound binds to an exosite, distinct from the active enzyme site.
iupac name: methyl N-[(2S)-2-[4-[5-[4-[[(2S)-2-[(3S)-3-amino-2-oxopiperidin-1-yl]-2-cyclohexylacetyl]amino]phenyl]pentoxy]phenyl]-3-quinolin-3-ylpropyl]carbamate
approved: f
ligand name: NTE-1
type: SyntheticOrganicLigand

[3H]oxotremorine-M
canonical SMILES: O=C1CCCN1CC#CC[N+](C)(C)C
isomeric SMILES: O=C1CCCN1CC#CC[N+](C)(C)C
in ch i key: CANZROMYQDHYHR-UHFFFAOYSA-N
in ch i: InChI=1S/C11H19N2O/c1-13(2,3)10-5-4-8-12-9-6-7-11(12)14/h6-10H2,1-3H3/q+1
comment: The position of the tritiated hydrogen is not specified in the available literature therefore we do not show it in our structure.
iupac name: trimethyl-[4-(2-oxopyrrolidin-1-yl)but-2-ynyl]azanium
approved: f
ligand name: [3H]oxotremorine-M
type: SyntheticOrganicLigand

[3H](+)telenzepine
in ch i key: VSWPGAIWKHPTKX-UHFFFAOYSA-N
in ch i: InChI=1S/C19H22N4O2S/c1-13-18-14(12-26-13)19(25)20-15-5-3-4-6-16(15)23(18)17(24)11-22-9-7-21(2)8-10-22/h3-6,12H,7-11H2,1-2H3,(H,20,25)
comment: The position of the tritiated hydrogen atom is not specified in the available literature therefore it is not shown in the structure here.
iupac name: 1-methyl-10-[2-(4-methylpiperazin-1-yl)acetyl]-5H-thieno[3,4-b][1,5]benzodiazepin-4-one
approved: f
ligand name: [3H](+)telenzepine
type: SyntheticOrganicLigand

[3H]acetylcholine
canonical SMILES: CC(=O)OCC[N+](C)(C)C
isomeric SMILES: CC(=O)OCC[N+](C)(C)C
in ch i key: OIPILFWXSMYKGL-UHFFFAOYSA-N
in ch i: InChI=1S/C7H16NO2/c1-7(9)10-6-5-8(2,3)4/h5-6H2,1-4H3/q+1
comment: The position of the tritiated hydrogen atom is not specified in the available literature therefore is not shown in the structure here.
iupac name: 2-acetyloxyethyl-trimethylazanium
approved: f
ligand name: [3H]acetylcholine
type: SyntheticOrganicLigand

[3H]tiotropium
in ch i key: LERNTVKEWCAPOY-FPISHFTHSA-N
in ch i: InChI=1S/C19H22NO4S2/c1-20(2)12-9-11(10-13(20)17-16(12)24-17)23-18(21)19(22,14-5-3-7-25-14)15-6-4-8-26-15/h3-8,11-13,16-17,22H,9-10H2,1-2H3/q+1/t11?,12-,13+,16-,17+
comment: The position of the tritiated hydrogen atom in this structure is not specified in the available literature therefore is not shown here.
iupac name: (1R,2R,4S,5S)-7-{[2-hydroxy-2,2-bis(thiophen-2-yl)acetyl]oxy}-9,9-dimethyl-3-oxa-9-azatricyclo[3.3.1.0^{2,4}]nonan-9-ium
approved: f
ligand name: [3H]tiotropium
type: SyntheticOrganicLigand

ML381
in ch i key: JMYDHMCYZKRDPD-AWEZNQCLSA-N
in ch i: InChI=1S/C21H21N3O4/c1-14(19-9-4-5-10-22-19)24(3)21(26)20-12-18(28-23-20)13-27-17-8-6-7-16(11-17)15(2)25/h4-12,14H,13H2,1-3H3/t14-/m0/s1
iupac name: 5-[(3-acetylphenoxy)methyl]-N-methyl-N-[(1S)-1-pyridin-2-ylethyl]-1,2-oxazole-3-carboxamide
xref: CHEMBL3185781
synonym: VU0488130-1
approved: f
ligand name: ML381
type: SyntheticOrganicLigand

ONO-9910539
in ch i key: URHZQBASTULQKJ-VVFBEHOQSA-N
in ch i: InChI=1S/C32H37NO8/c1-19(34)30-27(39-2)14-24(15-28(30)40-3)31(37)25(13-20-11-21-7-5-6-8-22(21)12-20)17-33-16-23(9-10-29(35)36)26(18-33)32(38)41-4/h5-8,14-16,18,20,25,31,37H,9-13,17H2,1-4H3,(H,35,36)/t25-,31+/m0/s1
comment: ONO-9910539 is an antagonist of the lysophosphatidic acid receptor 1 (LPA1) <Reference id=28696/>.
iupac name: 3-[1-[(2S,3S)-3-(4-acetyl-3,5-dimethoxyphenyl)-2-(2,3-dihydro-1H-inden-2-ylmethyl)-3-hydroxypropyl]-4-methoxycarbonylpyrrol-3-yl]propanoic acid
synonym: ON9
approved: f
ligand name: ONO-9910539
type: SyntheticOrganicLigand

ONO-9780307
in ch i key: PMPFDANPLYTSTM-PWUYWRBVSA-N
in ch i: InChI=1S/C30H35NO7/c1-18-26(36-2)12-22(13-27(18)37-3)29(34)24(11-19-9-20-7-5-6-8-21(20)10-19)16-31-15-23(14-28(32)33)25(17-31)30(35)38-4/h5-8,12-13,15,17,19,24,29,34H,9-11,14,16H2,1-4H3,(H,32,33)/t24-,29+/m0/s1
comment: ONO-9780307 is an antagonist of the lysophosphatidic acid receptor 1 (LPA1) <Reference id=28696/>.
iupac name: 2-[1-[(2S,3S)-2-(2,3-dihydro-1H-inden-2-ylmethyl)-3-(3,5-dimethoxy-4-methylphenyl)-3-hydroxypropyl]-4-methoxycarbonylpyrrol-3-yl]acetic acid
synonym: ON7
synonym: ONO9780307
approved: f
ligand name: ONO-9780307
type: SyntheticOrganicLigand

ONO-3080573
in ch i key: FVESDCZDESZGHA-URLMMPGGSA-N
in ch i: InChI=1S/C31H34O7/c1-19-26(35-2)16-22(17-27(19)36-3)29(32)28(38-25-14-20-6-4-5-7-21(20)15-25)18-37-24-10-8-23(9-11-24)31(12-13-31)30(33)34/h4-11,16-17,25,28-29,32H,12-15,18H2,1-3H3,(H,33,34)/t28-,29+/m0/s1
comment: ONO-3080573 is an antagonist of the lysophosphatidic acid receptor 1 (LPAR1) <Reference id=28696/>.
iupac name: 1-[4-[(2S,3R)-2-(2,3-dihydro-1H-inden-2-yloxy)-3-(3,5-dimethoxy-4-methylphenyl)-3-hydroxypropoxy]phenyl]cyclopropane-1-carboxylic acid
synonym: ON3
approved: f
ligand name: ONO-3080573
type: SyntheticOrganicLigand

MQ1
in ch i key: DFWKNBVJNXPUBW-LJQANCHMSA-N
in ch i: InChI=1S/C27H31N3O2/c1-18-25(29-27(31)21-7-10-24(11-8-21)32-17-20-5-6-20)12-9-22-15-23(16-28-26(18)22)19(2)30-13-3-4-14-30/h7-12,15-16,19-20H,3-6,13-14,17H2,1-2H3,(H,29,31)/t19-/m1/s1
comment: MQ1 is reported as a negative allosteric modulator (NAM) of the melanin-concentrating hormone receptor 1 (MCHR1) <Reference id=28692/><Reference id=25562/>. Antagonists and NAMs of MCHR1 are being investigated for their potential to provide anti-obesity therapies.
iupac name: 4-(cyclopropylmethoxy)-N-[8-methyl-3-[(1R)-1-pyrrolidin-1-ylethyl]quinolin-7-yl]benzamide
xref: CHEMBL2059420
synonym: MQ-1
synonym: compound (R)-10a
approved: f
ligand name: MQ1
type: SyntheticOrganicLigand

AE9C90CB
in ch i key: AARSINSGAQDAKQ-REPLKXPHSA-N
in ch i: InChI=1S/C21H24N2O2/c1-23(14-19-17-12-22-13-18(17)19)20(24)21(25,15-8-4-2-5-9-15)16-10-6-3-7-11-16/h2-11,17-19,22,25H,12-14H2,1H3/t17-,18+,19-
comment: PubChem CID 9862598 represents this molecule with alternative stereochemistry.
iupac name: N-[(1R,5S,6R)-3-azabicyclo[3.1.0]hexan-6-ylmethyl]-2-hydroxy-N-methyl-2,2-diphenylacetamide
approved: f
ligand name: AE9C90CB
type: SyntheticOrganicLigand

LP99
in ch i key: LVDRREOUMKACNJ-BKMJKUGQSA-N
comment: LP99 is a selective inhibitor of the bromodomain-containing proteins BRD7 and BRD9 <Reference id=28661/>, proteins which participate in chromatin remodelling as part of the SWI/SNF complex. LP99 is a novel and useful chemical probe for investigating BRD7/9 function. This is a compound from the Structural Genomics Consortium's (SGC) Epigenetics Probes Collection.
iupac name: N-[(2R,3S)-2-(4-chlorophenyl)-1-(1,4-dimethyl-2-oxo-1,2-dihydroquinolin-7-yl)-6-oxopiperidin-3-yl]-2-methylpropane-1-sulfonamide
synonym: compound 60 [PMID: 25864491]
approved: f
ligand name: LP99
type: SyntheticOrganicLigand

BAZ2-ICR
in ch i key: RRZVGDGTWNQAPW-UHFFFAOYSA-N
in ch i: InChI=1S/C20H19N7/c1-25-12-16(10-23-25)7-8-27-14-22-19(18-11-24-26(2)13-18)20(27)17-5-3-15(9-21)4-6-17/h3-6,10-14H,7-8H2,1-2H3
comment: BAZ2-ICR is a small molecule probe which binds to the BRD domains of the BRD domain-containing proteins BAZ2A and BAZ2B <Reference id=27431/>. This is a compound from the Structural Genomics Consortium's (SGC) Epigenetics Probes Collection.
iupac name: 4-[5-(1-methylpyrazol-4-yl)-3-[2-(1-methylpyrazol-4-yl)ethyl]imidazol-4-yl]benzonitrile
synonym: inhibitor 13 [PMID: 25719566]
approved: f
ligand name: BAZ2-ICR
type: SyntheticOrganicLigand

mercaptoacrylate inhibitor of calpain 1
canonical SMILES: OC(=O)C(=Cc1c[nH]c2c1cc(Br)cc2)S
isomeric SMILES: OC(=O)/C(=C/c1c[nH]c2c1cc(Br)cc2)/S
in ch i key: RLEKFRNXGFHPHZ-KMKOMSMNSA-N
in ch i: InChI=1S/C11H8BrNO2S/c12-7-1-2-9-8(4-7)6(5-13-9)3-10(16)11(14)15/h1-5,13,16H,(H,14,15)/b10-3-
comment: This compound is reported to inhibit porcine calpain 1 <Reference id=28660/>.
iupac name: (Z)-3-(5-bromo-1H-indol-3-yl)-2-sulfanylprop-2-enoic acid
xref: CHEMBL3221938
approved: f
ligand name: mercaptoacrylate inhibitor of calpain 1
type: SyntheticOrganicLigand

GE-137
in ch i key: UQYUYHHXESUXGH-ABPLELQPSA-N
comment: GE-137 is a cyclic peptide constructed as a fluorescent probe for the detection of colorectal polyps by binding to human tyrosine kinase c-Met <Reference id=28684/><Reference id=28687/>.
approved: f
ligand name: GE-137
type: PeptideLigand

AQ-RA 741
in ch i key: BCUGCHZRMKTPMU-UHFFFAOYSA-N
in ch i: InChI=1S/C27H37N5O2/c1-3-30(4-2)17-8-7-10-21-14-18-31(19-15-21)20-25(33)32-24-13-6-5-11-22(24)27(34)29-23-12-9-16-28-26(23)32/h5-6,9,11-13,16,21H,3-4,7-8,10,14-15,17-20H2,1-2H3,(H,29,34)
iupac name: 11-[2-[4-(4-diethylaminobutyl)piperidin-1-yl]acetyl]-5H-pyrido[2,3-b][1,4]benzodiazepin-6-one
xref: CHEMBL43383
approved: f
ligand name: AQ-RA 741
type: SyntheticOrganicLigand

UH-AH 37
in ch i key: UFJWXHOFKIGIAF-UHFFFAOYSA-N
in ch i: InChI=1S/C21H22ClN3O2/c1-24-11-9-14(10-12-24)13-19(26)25-18-8-3-2-5-15(18)21(27)23-17-7-4-6-16(22)20(17)25/h2-8,14H,9-13H2,1H3,(H,23,27)
iupac name: 1-chloro-11-[2-(1-methylpiperidin-4-yl)acetyl]-5H-benzo[b][1,4]benzodiazepin-6-one
approved: f
ligand name: UH-AH 37
type: SyntheticOrganicLigand

SGC707
canonical SMILES: O=C(Nc1ccc2c(c1)ccnc2)NCC(=O)N1CCCC1
isomeric SMILES: O=C(Nc1ccc2c(c1)ccnc2)NCC(=O)N1CCCC1
in ch i key: DMIDPTCQPIJYFE-UHFFFAOYSA-N
in ch i: InChI=1S/C16H18N4O2/c21-15(20-7-1-2-8-20)11-18-16(22)19-14-4-3-13-10-17-6-5-12(13)9-14/h3-6,9-10H,1-2,7-8,11H2,(H2,18,19,22)
comment: SGC707 is a cell permeable, potent and selective chemical probe for protein arginine methyltransferase 3 (PRMT3), which allosterically inhibits enzyme activity <Reference id=28638/>. This is a compound from the Structural Genomics Consortium's (SGC) Epigenetics Probes Collection.
iupac name: 1-isoquinolin-6-yl-3-(2-oxo-2-pyrrolidin-1-ylethyl)urea
approved: f
ligand name: SGC707
type: SyntheticOrganicLigand

peptide 4 [PMID: 18294843]
in ch i key: VZQHRKZCAZCACO-PYJNHQTQSA-N
in ch i: InChI=1S/C20H36N8O6/c1-9(2)14(18(32)27-12(5)19(33)34)28-16(30)11(4)25-15(29)10(3)26-17(31)13(21)7-6-8-24-20(22)23/h9-10,12-14H,4,6-8,21H2,1-3,5H3,(H,25,29)(H,26,31)(H,27,32)(H,28,30)(H,33,34)(H4,22,23,24)/t10-,12-,13-,14-/m0/s1
comment: Peptide 4 is reported as an inhibitor of tripeptidyl peptidase II (TPP2) <Reference id=28678/>. TPP2 is vital for essential processes such as antigen processing, apoptosis and cell division, with inhibitors predicted to have clinical potential in muscle wasting diseases, obesity, and cancer <Reference id=28679/>.
iupac name: (2S)-2-[[(2S)-2-[2-[[(2S)-2-[[(2S)-2-amino-5-(diaminomethylideneamino)pentanoyl]amino]propanoyl]amino]prop-2-enoylamino]-3-methylbutanoyl]amino]propanoic acid
xref: CHEMBL263633
approved: f
ligand name: peptide 4 [PMID: 18294843]
type: SyntheticOrganicLigand

example 8 [WO1999033801A1]
in ch i key: GNYDXSHWPPTVEX-CMPLNLGQSA-N
in ch i: InChI=1S/C15H17F4N3O2/c1-2-10(20)14(24)22-11-5-3-4-9(16)8(11)6-12(22)13(23)21-7-15(17,18)19/h3-5,10,12H,2,6-7,20H2,1H3,(H,21,23)/t10-,12+/m0/s1
comment: Example 8 binds to and inhibits the activity of tripeptidyl peptidase II (TPP2) <Reference id=28676/>. TPP2 is vital for essential processes such as antigen processing, apoptosis and cell division, with inhibitors predicted to have clinical potential in muscle wasting diseases, obesity, and cancer <Reference id=28679/>.
iupac name: (2R)-1-[(2S)-2-aminobutanoyl]-4-fluoro-N-(2,2,2-trifluoroethyl)-2,3-dihydroindole-2-carboxamide
approved: f
ligand name: example 8 [WO1999033801A1]
type: SyntheticOrganicLigand

mavorixafor
in ch i key: WVLHHLRVNDMIAR-IBGZPJMESA-N
in ch i: InChI=1S/C21H27N5/c22-12-3-4-14-26(15-20-24-17-9-1-2-10-18(17)25-20)19-11-5-7-16-8-6-13-23-21(16)19/h1-2,6,8-10,13,19H,3-5,7,11-12,14-15,22H2,(H,24,25)/t19-/m0/s1
comment: Mavorixafor (AMD070) is a potent, selective and bioavailable CXCR4 chemokine receptor allosteric antagonist <Reference id=28674/>. Originally developed for HIV treatment, it is now being repurposed by X4 Pharmaceuticals as X4P-001 for the treatment of WHIM syndrome, a sub-type of a primary immunodeficiency disease caused by CXCR4 mutations. The compound is exemplified in a process patent US7332605 and as compound 89 from a series of 169 analogues in WO2003055876 but neither filing includes activity data.
iupac name: N-(1H-benzimidazol-2-ylmethyl)-N-[(8S)-5,6,7,8-tetrahydroquinolin-8-yl]butane-1,4-diamine
xref: CHEMBL518924
synonym: AMD11070
synonym: X4P-001-IO
synonym: AMD 070
synonym: AMD-070
synonym: compound 2 [PMID: 20297846]
synonym: X4P-001-LD
synonym: AMD-11070
synonym: X4P-001
approved: f
ligand name: mavorixafor
type: SyntheticOrganicLigand

CID16197121
in ch i key: DPIFUIZFNOZKRB-DFIYOIEZSA-N
in ch i: InChI=1S/C25H27NO4S/c1-2-29-25-19(12-8-14-27)20(21-16-31-23-13-7-6-11-18(21)23)15-22(30-25)24(28)26-17-9-4-3-5-10-17/h3-7,9-11,13,15-16,19-20,25,27H,2,8,12,14H2,1H3,(H,26,28)/t19-,20+,25-/m0/s1
comment: Ras-Converting Enzyme (RCE1) iInhibitor from a confirmatory PubChem BioAssay. This protein is one of of the post-prenylation-processing enzymes that are targets for oncogenesis.
iupac name: (4R,5S,6S)-4-(1-benzothiophen-3-yl)-6-ethoxy-5-(3-hydroxypropyl)-N-phenyl-5,6-dihydro-4H-pyran-2-carboxamide
xref: CHEMBL1302410
approved: f
ligand name: CID16197121
type: SyntheticOrganicLigand

compound 29e [PMID: 23631440]
in ch i key: MUWDEQLPHWVPPA-GOTSBHOMSA-N
in ch i: InChI=1S/C24H31N3O5S2/c1-18(28)25-15-7-3-6-10-24(29)27-16-22(23(33)17-27)26-34(30,31)21-13-11-20(12-14-21)32-19-8-4-2-5-9-19/h2,4-5,8-9,11-14,22-23,26,33H,3,6-7,10,15-17H2,1H3,(H,25,28)/t22-,23-/m0/s1
comment: Compound 29e is reported as an inhibitor of matrix metallopeptidases, with high affinity for MMP9 and MMP14 <Reference id=28672/>.
iupac name: N-[6-oxo-6-[(3S,4S)-3-[(4-phenoxyphenyl)sulfonylamino]-4-sulfanylpyrrolidin-1-yl]hexyl]acetamide
xref: CHEMBL2380402
approved: f
ligand name: compound 29e [PMID: 23631440]
type: SyntheticOrganicLigand

GSK484
in ch i key: BDYDINKSILYBOL-WMZHIEFXSA-N
in ch i: InChI=1S/C27H31N5O3/c1-30-25-20(11-18(13-24(25)35-2)27(34)31-10-9-23(33)19(28)15-31)29-26(30)22-12-17-5-3-4-6-21(17)32(22)14-16-7-8-16/h3-6,11-13,16,19,23,33H,7-10,14-15,28H2,1-2H3/t19-,23+/m0/s1
comment: GSK484 binds to peptidyl arginine deiminase, type IV (PADI4; Q9UM07) and inhibits its activity <Reference id=28671/>. PADI4 contributes to regulating the histone code by effecting the citrullination/deimination of histones. PADI4 has strong associations with cancer and immune and inflammatory processes. GSK484 will be a useful tool to enhance understanding of the normal and pathological functions of PADI4. This is a compound from the Structural Genomics Consortium's (SGC) Epigenetics Probes Collection, developed in collaboration with GlaxoSmithKline (GSK).
iupac name: [(3S,4R)-3-amino-4-hydroxypiperidin-1-yl]-[2-[1-(cyclopropylmethyl)indol-2-yl]-7-methoxy-1-methylbenzimidazol-5-yl]methanone
synonym: GSK-484
synonym: GSK 484
approved: f
ligand name: GSK484
type: SyntheticOrganicLigand

KDOAM25
canonical SMILES: CCN(C(=O)CNCc1nccc(c1)C(=O)N)CCN(C)C
isomeric SMILES: CCN(C(=O)CNCc1nccc(c1)C(=O)N)CCN(C)C
in ch i key: PNFMVADNCOGWME-UHFFFAOYSA-N
in ch i: InChI=1S/C15H25N5O2/c1-4-20(8-7-19(2)3)14(21)11-17-10-13-9-12(15(16)22)5-6-18-13/h5-6,9,17H,4,7-8,10-11H2,1-3H3,(H2,16,22)
comment: KDOAM25 is a small molecule tool compound useful for studying the function of the KDM5 family of demethylase proteins. KDM5 proteins remove H3K4me3 and H3K4me2 histone marks and is therefore central to regulating the histone code. KDM5 family members have been suggested as potential oncogenes <Reference id=28667/><Reference id=24168/>, with KDM5C also implicated in autism <Reference id=28668/> and X-linked intellectual disability <Reference id=28669/>. This is a compound from the Structural Genomics Consortium's (SGC) Epigenetics Probes Collection.
iupac name: 2-[[[2-[2-(dimethylamino)ethyl-ethylamino]-2-oxoethyl]amino]methyl]pyridine-4-carboxamide
synonym: KDOAM-25
approved: f
ligand name: KDOAM25
type: SyntheticOrganicLigand

PFI-4
in ch i key: QCIJLRJBZDBVDB-UHFFFAOYSA-N
in ch i: InChI=1S/C21H24N4O3/c1-23-17-12-15(22-20(26)14-8-4-5-9-19(14)28-3)16(25-10-6-7-11-25)13-18(17)24(2)21(23)27/h4-5,8-9,12-13H,6-7,10-11H2,1-3H3,(H,22,26)
comment: This compound from the Structural Genomics Consortium's (SGC) Epigenetics Probes Collection, is a useful tool for studying the function of the bromodomain-containing protein, BRPF1. BRPF proteins 1, 2 and 3 provide the scaffold for the formation of MYST complexes which play essential functions in DNA repair, recombination, replication and activation of transcription. PFI-4 is selective for the BRPF1B isoform. The BRPF1A isoform contains an amino acid insertion which prevents its binding to acetylated histone peptides.
iupac name: N-(1,3-dimethyl-2-oxo-6-pyrrolidin-1-ylbenzimidazol-5-yl)-2-methoxybenzamide
approved: f
ligand name: PFI-4
type: SyntheticOrganicLigand

[3H]glutamine
canonical SMILES: NC(=O)CCC(C(=O)O)N
isomeric SMILES: NC(=O)CC[C@@H](C(=O)O)N
in ch i key: ZDXPYRJPNDTMRX-VKHMYHEASA-N
in ch i: InChI=1S/C5H10N2O3/c6-3(5(9)10)1-2-4(7)8/h3H,1-2,6H2,(H2,7,8)(H,9,10)/t3-/m0/s1
iupac name: (2S)-2-amino-4-carbamoylbutanoic acid
xref: CHEMBL930
synonym: [3H]-glutamine
approved: f
ligand name: [3H]glutamine
type: SyntheticOrganicLigand

compound 19 [PMID: 8831774]
in ch i key: CZZWUFZBGQIPTE-UHFFFAOYSA-N
in ch i: InChI=1S/C27H35N3O6/c1-4-21(24(32)26(34)28-16-23(31)20-13-9-6-10-14-20)29-25(33)22(15-18(2)3)30-27(35)36-17-19-11-7-5-8-12-19/h5-14,18,21-23,31H,4,15-17H2,1-3H3,(H,28,34)(H,29,33)(H,30,35)
comment: This compound is reported to inhibit the activity of calpain 2 (CAPN2) <Reference id=28659/>.
iupac name: benzyl N-[1-[[1-[(2-hydroxy-2-phenylethyl)amino]-1,2-dioxopentan-3-yl]amino]-4-methyl-1-oxopentan-2-yl]carbamate
xref: CHEMBL130506
synonym: Z-Leu-Abu-CONH-CH2-CHOH-Ph
approved: f
ligand name: compound 19 [PMID: 8831774]
type: SyntheticOrganicLigand

compound 25 [PMID: 18068976]
in ch i key: JRYQAIVHIZIBOQ-UHFFFAOYSA-N
in ch i: InChI=1S/C25H37N3O7S/c1-18-5-2-3-6-20(18)19-9-13-28(14-10-19)36(33,34)17-25(23(30)26-32)11-15-27(16-12-25)24(31)35-22-8-4-7-21(22)29/h2-3,5-6,19,21-22,29,32H,4,7-17H2,1H3,(H,26,30)
comment: Compound 25 is reported to selectively inhibit the activity of ADAM metallopeptidase domain 10 (ADAM10), relative to MMP1 and MMP2 <Reference id=28658/>.
iupac name: (2-hydroxycyclopentyl) 4-(hydroxycarbamoyl)-4-[[4-(2-methylphenyl)piperidin-1-yl]sulfonylmethyl]piperidine-1-carboxylate
xref: CHEMBL442432
approved: f
ligand name: compound 25 [PMID: 18068976]
type: SyntheticOrganicLigand

RS 39066
in ch i key: CEEASCNCHQSPKF-AEFFLSMTSA-N
in ch i: InChI=1S/C22H33N3O6/c1-13(2)10-16(12-19(26)25-30)20(27)24-18(11-14(3)4)21(28)23-17-8-6-15(7-9-17)22(29)31-5/h6-9,13-14,16,18,30H,10-12H2,1-5H3,(H,23,28)(H,24,27)(H,25,26)/t16-,18+/m1/s1
comment: RS 39066 inhibits matrix metallopeptidase 7 (matrilysin) (MMP7) <Reference id=28657/>.
iupac name: methyl 4-[[(2S)-2-[[(2R)-2-[2-(hydroxyamino)-2-oxoethyl]-4-methylpentanoyl]amino]-4-methylpentanoyl]amino]benzoate
xref: CHEMBL288896
synonym: RS-39066
synonym: RS39066
approved: f
ligand name: RS 39066
type: SyntheticOrganicLigand

Ac-VEID-CHO
in ch i key: KYUFGGNCJRWMDN-GOYXDOSHSA-N
in ch i: InChI=1S/C22H36N4O9/c1-6-12(4)19(22(35)24-14(10-27)9-17(31)32)26-20(33)15(7-8-16(29)30)25-21(34)18(11(2)3)23-13(5)28/h10-12,14-15,18-19H,6-9H2,1-5H3,(H,23,28)(H,24,35)(H,25,34)(H,26,33)(H,29,30)(H,31,32)/t12-,14-,15-,18-,19-/m0/s1
comment: Ac-VEID-CHO is reported as an inhibitor of caspase 6 (CASP6) <Reference id=28656/>. Caspase 6 has been investigated as a potential drug target for the treatment of Parkinson's disease, based on the role of the enzyme in mediating the cleavage of the huntingtin protein into toxic fragments.
iupac name: (4S)-4-[[(2S)-2-acetamido-3-methylbutanoyl]amino]-5-[[(2S,3S)-1-[[(2S)-1-carboxy-3-oxopropan-2-yl]amino]-3-methyl-1-oxopentan-2-yl]amino]-5-oxopentanoic acid
xref: CHEMBL478081
synonym: acetyl-Val-Ile-Asp-aldehyde
approved: f
ligand name: Ac-VEID-CHO
type: SyntheticOrganicLigand

compound I3 [PMID: 23428964]
canonical SMILES: O=C1Cc2c(ccc(c2CCC1N)Br)c1ccccc1
isomeric SMILES: O=C1Cc2c(ccc(c2CCC1N)Br)c1ccccc1
in ch i key: XFZZDIHCNHYESF-UHFFFAOYSA-N
in ch i: InChI=1S/C17H16BrNO/c18-15-8-6-12(11-4-2-1-3-5-11)14-10-17(20)16(19)9-7-13(14)15/h1-6,8,16H,7,9-10,19H2
comment: Compound I3 is reported as a potent and selective inhibitor of aminopeptidase-N (ANPEP aka APN) <Reference id=28655/>. ANPEP inhibitors are hypothesised to have anti-angiogenic activity with potential use as anti-cancer therapeutics.
iupac name: 7-amino-1-bromo-4-phenyl-5,7,8,9-tetrahydrobenzo[7]annulen-6-one
xref: CHEMBL1852660
approved: f
ligand name: compound I3 [PMID: 23428964]
type: SyntheticOrganicLigand

ARI-3531
canonical SMILES: OB(C1CCCN1C(=O)C(C(C)C)NC(=O)c1ccncc1)O
in ch i key: MXZNUGFCDVAXLG-CHWSQXEVSA-N
in ch i: InChI=1S/C15H22BN3O4/c1-10(2)13(18-14(20)11-5-7-17-8-6-11)15(21)19-9-3-4-12(19)16(22)23/h5-8,10,12-13,22-23H,3-4,9H2,1-2H3,(H,18,20)/t12-,13-/m1/s1
comment: ARI-3531 is reported to selectively inhibit prolyl endopeptidase (PREP) compared to fibroblast activation protein, alpha (FAP) <Reference id=28654/>. The stereochemistry represented here matches that provided in the referenced article <Reference id=28654/>.
iupac name: [(2S)-1-[(2R)-3-methyl-2-(pyridin-4-ylformamido)butanoyl]pyrrolidin-2-yl]boronic acid
synonym: compound 22 [PMID: 23594271]
approved: f
ligand name: ARI-3531
type: SyntheticOrganicLigand

ARI-3099
canonical SMILES: OB(C1CCCN1C(=O)C(NC(=O)c1ccncc1)C)O
in ch i key: DRBWRJPFNOBNIO-KOLCDFICSA-N
in ch i: InChI=1S/C13H18BN3O4/c1-9(16-12(18)10-4-6-15-7-5-10)13(19)17-8-2-3-11(17)14(20)21/h4-7,9,11,20-21H,2-3,8H2,1H3,(H,16,18)/t9-,11+/m1/s1
comment: ARI-3099 is reported as an inhibitor of fibroblast activation protein, alpha (FAP) <Reference id=28654/>. FAP is being investigated as a novel anti-cancer drug target, given the role of the enzyme in tumour invasion and metastasis. Bachovchin et al. (2014) report inhibition of acylaminoacyl-peptide hydrolase (APEH) by this compound <Reference id=28714/>.
xref: CHEMBL2333026
synonym: compound 6 [PMID: 23594271]
synonym: compound 226 [PMID: 24997602]
synonym: Py(D)AlaboroPro
approved: f
ligand name: ARI-3099
type: SyntheticOrganicLigand

AZD5438
in ch i key: WJRRGYBTGDJBFX-UHFFFAOYSA-N
in ch i: InChI=1S/C18H21N5O2S/c1-12(2)23-13(3)20-11-17(23)16-9-10-19-18(22-16)21-14-5-7-15(8-6-14)26(4,24)25/h5-12H,1-4H3,(H,19,21,22)
comment: AZD5438 is a potent oral inhibitor of cyclin dependent kinases (CDKs) 1, 2 and 9 <Reference id=28188/>.
iupac name: 4-(2-methyl-3-propan-2-ylimidazol-4-yl)-N-(4-methylsulfonylphenyl)pyrimidin-2-amine
xref: CHEMBL488436
synonym: AZD 5438
synonym: AZD-5438
approved: f
ligand name: AZD5438
type: SyntheticOrganicLigand

compound 2 [PMID: 11934595]
in ch i key: PGEHBYYTLWHQOM-LJQANCHMSA-N
in ch i: InChI=1S/C22H22N2O7S2/c1-29-16-5-7-18(8-6-16)33(27,28)24(13-15-4-9-20-21(11-15)31-14-30-20)19(22(25)23-26)12-17-3-2-10-32-17/h2-11,19,26H,12-14H2,1H3,(H,23,25)/t19-/m1/s1
comment: Compound 2 is reported as an inhibitor of bone morphogenetic protein 1 (BMP1), or procollagen C-proteinase in this referenced article <Reference id=28653/>. BMP1 is considered a druggable molecular target for the development of anti-fibrotic agents because collagen substrates are involved in forming functional collagen fibrils.
iupac name: (2R)-2-[1,3-benzodioxol-5-ylmethyl-(4-methoxyphenyl)sulfonylamino]-N-hydroxy-3-thiophen-2-ylpropanamide
xref: CHEMBL282896
approved: f
ligand name: compound 2 [PMID: 11934595]
type: SyntheticOrganicLigand

citibrasine
in ch i key: QYPQTPVQPNLXHV-UHFFFAOYSA-N
in ch i: InChI=1S/C17H17NO6/c1-18-11-8(6-5-7-9(11)19)13(20)10-12(18)15(22-2)17(24-4)16(23-3)14(10)21/h5-7,19,21H,1-4H3
comment: Citibrasine (an acridone alkaloid derivative extracted of the stem bark of Swinglea glutinosa) is reported as a substrate-competitive inhibitor of cathepsin V <Reference id=28650/>. Cathepsin V has been considered as a potential druggable molecular target because of the role that the enzyme plays in cancer progression.
iupac name: 1,5-dihydroxy-2,3,4-trimethoxy-10-methylacridin-9-one
xref: CHEMBL1668599
synonym: compound 7 [PMID: 21277783]
approved: f
ligand name: citibrasine
type: NaturalProductLigand

Pam2CSK4
in ch i key: LJUIOEFZFQRWJG-KKIBDXJDSA-N
comment: TLR2/6 agonist; induces TNFα production.
iupac name: (2S)-6-amino-2-[[(2S)-6-amino-2-[[(2S)-6-amino-2-[[(2S)-6-amino-2-[[(2S)-2-[[(2R)-2-amino-3-[2,3-di(hexadecanoyloxy)propylsulfanyl]propanoyl]amino]-3-hydroxypropanoyl]amino]hexanoyl]amino]hexanoyl]amino]hexanoyl]amino]hexanoic acid
approved: f
ligand name: Pam2CSK4
type: PeptideLigand

compound 9 [PMID: 3514912]
canonical SMILES: O=C(c1ccc(cc1)N=C(N)N)Oc1ccc(cc1)C
isomeric SMILES: O=C(c1ccc(cc1)N=C(N)N)Oc1ccc(cc1)C
in ch i key: OELAPCOUDOSGBC-UHFFFAOYSA-N
in ch i: InChI=1S/C15H15N3O2/c1-10-2-8-13(9-3-10)20-14(19)11-4-6-12(7-5-11)18-15(16)17/h2-9H,1H3,(H4,16,17,18)
comment: Compound 9 is reported as an inhibitor of human acrosin (ACR) <Reference id=28648/>. Inhibition of acrosin would be expected to inhibit the acrosome reaction preventing lysis of the zona pellucida which is essential for spermatozoan penetration through the oocyte membrane. Small molecule inhibitors of acrosin were therefore of pharmaceutical interest as nonhormonal contraceptive agents.
iupac name: (4-methylphenyl) 4-(diaminomethylideneamino)benzoate
xref: CHEMBL151454
approved: f
ligand name: compound 9 [PMID: 3514912]
type: SyntheticOrganicLigand

compound 14 [PMID: 23634668]
in ch i key: NHHPRDYQOKYIBK-VWLOTQADSA-N
in ch i: InChI=1S/C28H28N6O2/c1-20(35)30-25(19-21-9-3-2-4-10-21)28(36)34-17-15-33(16-18-34)27-22-11-5-6-12-23(22)31-26(32-27)24-13-7-8-14-29-24/h2-14,25H,15-19H2,1H3,(H,30,35)/t25-/m0/s1
comment: Compound 14 is reported as a selective inhibitor of methionyl aminopeptidase 1 (METAP1) <Reference id=28647/>.
iupac name: N-[(2S)-1-oxo-3-phenyl-1-[4-(2-pyridin-2-ylquinazolin-4-yl)piperazin-1-yl]propan-2-yl]acetamide
approved: f
ligand name: compound 14 [PMID: 23634668]
type: SyntheticOrganicLigand

compound 3 [PMID: 17942791]
in ch i key: PSCFZETTYRDCRM-UHFFFAOYSA-N
in ch i: InChI=1S/C23H18N2O3/c26-22-19(13-10-16-7-4-14-24-21(16)22)20(15-5-2-1-3-6-15)25-18-11-8-17(9-12-18)23(27)28/h1-14,20,25-26H,(H,27,28)
comment: Compound 3 is reported as a small molecule inhibitor of Ras converting CAAX endopeptidase 1 (RCE1) <Reference id=28646/>.
iupac name: 4-[[(8-hydroxyquinolin-7-yl)-phenylmethyl]amino]benzoic acid
xref: CHEMBL1979298
approved: f
ligand name: compound 3 [PMID: 17942791]
type: SyntheticOrganicLigand

compound 13 [PMID: 23412139]
in ch i key: IKFZEHQGULJMKI-SFHVURJKSA-N
in ch i: InChI=1S/C18H18N4OS/c1-4-5-12-6-13(10-20-9-12)14-7-15(24-11-14)18(2)8-16(23)22(3)17(19)21-18/h6-7,9-11H,8H2,1-3H3,(H2,19,21)/t18-/m0/s1
comment: This compound is an investigational small molecule inhibitor of beta-site APP-cleaving enzyme 1 (BACE1, β-secretase) <Reference id=27842/> (n.b. this is cpd 13 in the reference, not cpd 16 declared as the lead in this article).
iupac name: (6S)-2-amino-3,6-dimethyl-6-[4-(5-prop-1-ynylpyridin-3-yl)thiophen-2-yl]-5H-pyrimidin-4-one
xref: CHEMBL2151141
approved: f
ligand name: compound 13 [PMID: 23412139]
type: SyntheticOrganicLigand

compound 20 [PMID: 12372533]
in ch i key: JAXFJECJQZDFJS-XHEPKHHKSA-N
comment: Compound 20 is reported in a medicinal chemistry study to identify inhibitors of the HCV NS3 protease <Reference id=28643/>. Compound 20 is a peptide boronic acid containing an extended, hydrophobic P1 residue. The boronic acid/P1 moeity is ligated to the small peptide H-Asp-Glu-Val-Val-Pro. The compound also inhibits human chymotrypsin C (CTRC).
xref: CHEMBL107656
approved: f
ligand name: compound 20 [PMID: 12372533]
type: SyntheticOrganicLigand

compound 35 [PMID: 24157366]
in ch i key: ABJSOROVZZKJGI-OCYUSGCXSA-N
comment: This a tool compound reported as a prolylcarboxypeptidase (PRCP) inhibitor <Reference id=28640/>. Additional structure-activity relationship (SAR) information for this (Example 12) and related compounds is provided in patent US8669252 B2 <Reference id=28641/>. Prolylcarboxypeptidase is being investigated as a novel target for anti-obesity therapeutics due to its role in regulating metabolism.
iupac name: (1R,2R,4R)-2-(4-bromophenyl)-N-[(4-chlorophenyl)-(2-fluoropyridin-4-yl)methyl]-4-morpholin-4-ylcyclohexane-1-carboxamide
xref: CHEMBL3086040
approved: f
ligand name: compound 35 [PMID: 24157366]
type: SyntheticOrganicLigand

compound 15c [PMID: 21536437]
in ch i key: SIXCEPSXNLUZTE-UHFFFAOYSA-N
comment: Compound 15c is reported as an inhibitor of ADAM metallopeptidase with thrombospondin type 1 motif, 4 (ADAMTS4 aka aggrecanase-1) and ADAM metallopeptidase with thrombospondin type 1 motif, 5 ((ADAMTS5 aka aggrecanase-2) <Reference id=28639/>.
iupac name: N-[4-[[4-[2-(4-chloro-2-methylphenyl)ethyl]piperidin-1-yl]sulfonylmethyl]-1-(cyclobutanecarbonyl)piperidin-4-yl]-N-hydroxyformamide
xref: CHEMBL1784369
approved: f
ligand name: compound 15c [PMID: 21536437]
type: SyntheticOrganicLigand

compound 15 [PMID: 8709131]
canonical SMILES: C(=Cc1ccc(cc1)c1ccccc1)C1CN2CCC1CC2
isomeric SMILES: C(=C/c1ccc(cc1)c1ccccc1)/C1CN2CCC1CC2
in ch i key: OBORHRVWTIDYCG-DHZHZOJOSA-N
in ch i: InChI=1S/C21H23N/c1-2-4-18(5-3-1)19-9-6-17(7-10-19)8-11-21-16-22-14-12-20(21)13-15-22/h1-11,20-21H,12-16H2/b11-8+
iupac name: 3-[(E)-2-(4-phenylphenyl)ethenyl]-1-azabicyclo[2.2.2]octane
xref: CHEMBL327957
approved: f
ligand name: compound 15 [PMID: 8709131]
type: SyntheticOrganicLigand

1G244
in ch i key: ZKIQFLSGMMYCGS-SANMLTNESA-N
in ch i: InChI=1S/C29H30F2N4O2/c30-24-9-5-20(6-10-24)28(21-7-11-25(31)12-8-21)34-15-13-33(14-16-34)27(36)17-26(32)29(37)35-18-22-3-1-2-4-23(22)19-35/h1-12,26,28H,13-19,32H2/t26-/m0/s1
comment: This compound is a potent and selective inhibitor of dipeptidyl-peptidases 8 and 9 (DPP8/9) <Reference id=28635/>. This is the (S)-isomer of <Ligand id=6536/>.
iupac name: (2S)-2-amino-4-[4-[bis(4-fluorophenyl)methyl]piperazin-1-yl]-1-(1,3-dihydroisoindol-2-yl)butane-1,4-dione
xref: CHEMBL1814633
approved: f
ligand name: 1G244
type: SyntheticOrganicLigand

compound 24dd [PMID: 20684603]
in ch i key: JGJABGSOYWQCSC-UHFFFAOYSA-N
in ch i: InChI=1S/C22H20Cl2N6O/c1-13-17(11-25)20(16-6-5-14(23)10-18(16)24)30-12-19(29-22(30)28-13)21(31)27-9-7-15-4-2-3-8-26-15/h2-6,8,10,12H,7,9,11,25H2,1H3,(H,27,31)
comment: This compound is a selective inhibitor of dipeptidyl-peptidase 4 (DPP4) <Reference id=28633/>.
iupac name: 6-(aminomethyl)-5-(2,4-dichlorophenyl)-7-methyl-N-(2-pyridin-2-ylethyl)imidazo[1,2-a]pyrimidine-2-carboxamide
xref: CHEMBL1215376
approved: f
ligand name: compound 24dd [PMID: 20684603]
type: SyntheticOrganicLigand

benzoquinazolinone 12
in ch i key: SXJQBWJPNSOKQV-UIOOFZCWSA-N
in ch i: InChI=1S/C28H27N5O2/c1-32-16-20(15-31-32)24-11-10-18(14-29-24)12-19-13-23-27(22-7-3-2-6-21(19)22)30-17-33(28(23)35)25-8-4-5-9-26(25)34/h2-3,6-7,10-11,13-17,25-26,34H,4-5,8-9,12H2,1H3/t25-,26-/m0/s1
iupac name: 3-[(1S,2S)-2-hydroxycyclohexyl]-6-{[6-(1-methyl-1H-pyrazol-4-yl)pyridin-3-yl]methyl}-3H,4H-benzo[h]quinazolin-4-one
approved: f
ligand name: benzoquinazolinone 12
type: SyntheticOrganicLigand

compound 2 [PMID: 26061392]
in ch i key: JMMXKBJIBAVJSU-UHFFFAOYSA-N
comment: This <Ligand id=5893/> photo prodrug shows proof of concept in loss-of-function and light-dependent recovery of efficacy in kinase and cellular assays <Reference id=28540/>.
iupac name: N‐{3‐[5‐(4‐chlorophenyl)‐1‐[(4,5‐dimethoxy‐2‐nitrophenyl)methyl]‐1H‐pyrrolo[2,3‐b]pyridine‐3‐carbonyl]‐2,4‐difluorophenyl}propane‐1‐sulfonamide
synonym: caged vemurafenib prodrug
approved: f
ligand name: compound 2 [PMID: 26061392]
type: SyntheticOrganicLigand

CYM2503
in ch i key: DSRPDMJWEFCXMI-GHKFOJCISA-N
in ch i: InChI=1S/C44H55N5O7/c1-27-23-39(50)47-37-25-29(20-21-30(27)37)46-40(51)36(19-12-22-45-42(53)56-44(2,3)4)48-41(52)38(24-28-13-6-5-7-14-28)49-43(54)55-26-35-33-17-10-8-15-31(33)32-16-9-11-18-34(32)35/h8-11,15-18,20-21,23,25,28,31,33,35-36,38H,5-7,12-14,19,22,24,26H2,1-4H3,(H,45,53)(H,46,51)(H,47,50)(H,48,52)(H,49,54)/t31?,33?,35?,36-,38-/m0/s1
comment: CYM2503 is reported as a positive allosteric modulator (PAM) of the GAL2 receptor which potentiates galanin-induced IP1 production in vitro <Reference id=20556/>. The compound has no affinity for the orthosteric galanin binding site of the receptor (as measured by its inability to displace iodinated galanin, or to induce IP1 accumulation on its own). The compound has no effect on GAL1 receptor activity.
iupac name: tert-butyl N-[(4S)-4-[(2S)-2-{[(9,9a-dihydro-4aH-fluoren-9-ylmethoxy)carbonyl]amino}-3-cyclohexylpropanamido]-4-[(4-methyl-2-oxo-1,2-dihydroquinolin-7-yl)carbamoyl]butyl]carbamate
synonym: CYM-2503
approved: f
ligand name: CYM2503
type: SyntheticOrganicLigand

TG7-171
in ch i key: NBHMEDLJHJCMEZ-UHFFFAOYSA-N
in ch i: InChI=1S/C24H31N3O/c1-4-26(5-2)22-13-11-20(12-14-22)18-24(28)25-15-8-16-27-19(3)17-21-9-6-7-10-23(21)27/h6-7,9-14,17H,4-5,8,15-16,18H2,1-3H3,(H,25,28)
iupac name: 2-[4-(diethylamino)phenyl]-N-[3-(2-methyl-1H-indol-1-yl)propyl]acetamide
approved: f
ligand name: TG7-171
type: SyntheticOrganicLigand

XAP044
canonical SMILES: Ic1ccc(cc1)Oc1coc2c(c1=O)ccc(c2)O
isomeric SMILES: Ic1ccc(cc1)Oc1coc2c(c1=O)ccc(c2)O
in ch i key: XXZKJJYWINSUMJ-UHFFFAOYSA-N
in ch i: InChI=1S/C15H9IO4/c16-9-1-4-11(5-2-9)20-14-8-19-13-7-10(17)3-6-12(13)15(14)18/h1-8,17H
comment: XAP044 exerts antagonist-like activity at the mGlu5 receptor, binding to a novel site within the extracellular Venus flytrap domain compared with known selective ligands <Reference id=28505/>, making this compound a negative allosteric modulator (NAM).
iupac name: 7-hydroxy-3-(4-iodophenoxy)chromen-4-one
synonym: 7-hydroxy-3-(4-iodophenoxy)-4H-chromen-4-one
approved: f
ligand name: XAP044
type: SyntheticOrganicLigand

alloswitch-1
canonical SMILES: COc1cc(N=Nc2ccccn2)ccc1NC(=O)c1ccccc1Cl
isomeric SMILES: COc1cc(/N=N/c2ccccn2)ccc1NC(=O)c1ccccc1Cl
in ch i key: JJRNGNCTPCWXGM-WCWDXBQESA-N
in ch i: InChI=1S/C19H15ClN4O2/c1-26-17-12-13(23-24-18-8-4-5-11-21-18)9-10-16(17)22-19(25)14-6-2-3-7-15(14)20/h2-12H,1H3,(H,22,25)/b24-23+
comment: Alloswitch-1 is the first reported photo-switchable negative allosteric modulator (NAM) for an endogenous G protein-coupled receptor <Reference id=28502/>, in this case a NAM of the mGlu5 metabotropic glutamate receptor. Violet light isomerizes the trans molecule to the cis molecule and green light reverses this isomerization <Reference id=28502/>. In dark conditions trans-alloswitch-1 antagonizes IP production by <Ligand id=1372/> (orthosteric agonist)-activated mGlu5 receptors. Exposure to violet light reduces this level of antagonism, indicating that the cis-isomer is less active as a NAM than the trans-isomer <Reference id=28502/>. The development of photo-switchable compounds is being pursued by pharmaceutical companies as a method to improve pharmacological selectivity by allowing precise spatio-temporal regulation of drug action <Reference id=34638/>.
iupac name: 2-chloro-N-{2-methoxy-4-[(E)-2-(pyridin-2-yl)diazen-1-yl]phenyl}benzamide
synonym: trans-alloswitch-1
approved: f
ligand name: alloswitch-1
type: SyntheticOrganicLigand

olesoxime
in ch i key: QNTASHOAVRSLMD-FCARAQADSA-N
in ch i: InChI=1S/C27H45NO/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28-29)13-15-26(20,4)25(22)14-16-27(23,24)5/h17-19,22-25,29H,6-16H2,1-5H3/b28-21-/t19-,22+,23-,24+,25+,26+,27-/m1/s1
comment: Olesoxime is an investigational cholesterol-like compound with potential as a therapeutic for amyotrophic lateral sclerosis (ALS) <Reference id=28493/><Reference id=28494/> or spinal muscular atrophy (SMA).
iupac name: (NZ)-N-[(8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-ylidene]hydroxylamine
synonym: TRO19622
synonym: TRO 19622
synonym: TRO-19622
synonym: cholest-4-en-3-one, oxime
approved: f
ligand name: olesoxime
type: SyntheticOrganicLigand

[14C]glutamine
canonical SMILES: NC(=O)CCC(C(=O)O)N
isomeric SMILES: NC(=O)CC[C@@H](C(=O)O)N
in ch i key: ZDXPYRJPNDTMRX-VKHMYHEASA-N
in ch i: InChI=1S/C5H10N2O3/c6-3(5(9)10)1-2-4(7)8/h3H,1-2,6H2,(H2,7,8)(H,9,10)/t3-/m0/s1
iupac name: (2S)-2-amino-4-carbamoylbutanoic acid
xref: CHEMBL930
synonym: [14C]-glutamine
approved: f
ligand name: [14C]glutamine
type: SyntheticOrganicLigand

ONO-AE1-437
in ch i key: ORSJUPRAHPZYRL-XHTUOEPPSA-N
in ch i: InChI=1S/C23H32O6S/c1-29-15-17-5-2-4-16(12-17)13-18(24)7-8-19-20(22(26)14-21(19)25)9-11-30-10-3-6-23(27)28/h2,4-5,7-8,12,18-21,24-25H,3,6,9-11,13-15H2,1H3,(H,27,28)/b8-7+/t18-,19-,20-,21-/m1/s1
iupac name: 4-[2-[(1R,2R,3R)-3-hydroxy-2-[(E,3S)-3-hydroxy-4-[3-(methoxymethyl)phenyl]but-1-enyl]-5-oxocyclopentyl]ethylsulfanyl]butanoic acid
xref: CHEMBL292964
approved: f
ligand name: ONO-AE1-437
type: SyntheticOrganicLigand

compound 14 [PMID: 25050158]
isomeric SMILES: OC(=O)C(=O)/C=C/c1cc(c(c(c1)C(C)(C)C)O)C(C)(C)C
in ch i key: XIQDGAUDNMVMCD-BQYQJAHWSA-N
in ch i: InChI=1S/C18H24O4/c1-17(2,3)12-9-11(7-8-14(19)16(21)22)10-13(15(12)20)18(4,5)6/h7-10,20H,1-6H3,(H,21,22)/b8-7+
comment: Compound 14 is reported as a negative allosteric modulator (NAM) of the GABAB receptor <Reference id=28491/>. Its structure is based on that of <Ligand id=1079/>, a positive allosteric modulator (PAM) of GABAB receptors.
iupac name: (3E)-4-(3,5-di-tert-butyl-4-hydroxyphenyl)-2-oxobut-3-enoic acid
approved: f
ligand name: compound 14 [PMID: 25050158]
type: SyntheticOrganicLigand

PF-04852946
in ch i key: MDVYCLAYSVNYDS-UHFFFAOYSA-N
in ch i: InChI=1S/C27H24N2O5/c1-33-23-10-8-22(9-11-23)25(30)29-15-14-27(17-29,26(31)32)18-34-24-12-6-21(7-13-24)20-4-2-19(16-28)3-5-20/h2-13H,14-15,17-18H2,1H3,(H,31,32)
comment: PF-04852946 is an EP2 receptor-selective antagonist
iupac name: 3-[[4-(4-cyanophenyl)phenoxy]methyl]-1-(4-methoxybenzoyl)pyrrolidine-3-carboxylic acid
synonym: PF04852946
synonym: PF 04852946
approved: f
ligand name: PF-04852946
type: SyntheticOrganicLigand

ONO-AE3-237
in ch i key: PDLHJVXUGHZZQP-QHCPKHFHSA-N
in ch i: InChI=1S/C29H28N2O5/c1-18-7-12-27-26(13-18)30(3)16-23(36-27)17-35-22-10-8-20(9-11-22)29(34)31-19(2)14-24-21(15-28(32)33)5-4-6-25(24)31/h4-14,23H,15-17H2,1-3H3,(H,32,33)/t23-/m0/s1
comment: ONO-AE3-237 has high DP1 antagonist selectivity and (sub)nanomolar affinity.
iupac name: 2-[1-[4-[[(2S)-4,6-dimethyl-2,3-dihydro-1,4-benzoxazin-2-yl]methoxy]benzoyl]-2-methylindol-4-yl]acetic acid
approved: f
ligand name: ONO-AE3-237
type: SyntheticOrganicLigand

Ro5028442
in ch i key: DRMVDBATNZBNEB-UHFFFAOYSA-N
in ch i: InChI=1S/C25H30ClN3O2/c1-27(2)13-14-29-16-21(20-8-7-19(26)15-23(20)29)24(30)28-11-9-25(10-12-28)22-6-4-3-5-18(22)17-31-25/h3-8,15,21H,9-14,16-17H2,1-2H3
comment: Ro5028442 is an investigational selective brain-penetrant antagonist of the vasopressin V1A receptor. The discovery of this compound is reported in <Reference id=28476/>, where it is compound 8.
iupac name: {2-[6-chloro-3-({3H-spiro[2-benzofuran-1,4'-piperidine]-1'-yl}carbonyl)-2,3-dihydro-1H-indol-1-yl]ethyl}dimethylamine
synonym: Ro-5028442
synonym: Ro 5028442
synonym: RG7713
synonym: RG-7713
approved: f
ligand name: Ro5028442
type: SyntheticOrganicLigand

biochanin A
canonical SMILES: COc1ccc(cc1)c1coc2c(c1=O)c(O)cc(c2)O
isomeric SMILES: COc1ccc(cc1)c1coc2c(c1=O)c(O)cc(c2)O
in ch i key: WUADCCWRTIWANL-UHFFFAOYSA-N
in ch i: InChI=1S/C16H12O5/c1-20-11-4-2-9(3-5-11)12-8-21-14-7-10(17)6-13(18)15(14)16(12)19/h2-8,17-18H,1H3
iupac name: 5,7-dihydroxy-3-(4-methoxyphenyl)chromen-4-one
xref: CHEMBL131921
synonym: 4'-methylgenistein
approved: f
ligand name: biochanin A
type: NaturalProductLigand

AZD8186
in ch i key: LMJFJIDLEAWOQJ-CQSZACIVSA-N
in ch i: InChI=1S/C24H25F2N3O4/c1-14(27-18-11-16(25)10-17(26)12-18)19-8-15(24(31)28(2)3)9-20-21(30)13-22(33-23(19)20)29-4-6-32-7-5-29/h8-14,27H,4-7H2,1-3H3/t14-/m1/s1
comment: AZD8186 is a selective inhibitor of PI3Kβ- and δ-mediated AKT signalling <Reference id=28470/>.
iupac name: 8-[(1R)-1-[(3,5-difluorophenyl)amino]ethyl]-N,N-dimethyl-2-(morpholin-4-yl)-4-oxo-4H-chromene-6-carboxamide
synonym: AZD-8186
synonym: AZD 8186
approved: f
ligand name: AZD8186
type: SyntheticOrganicLigand

compound 9g [PMID: 24412111]
in ch i key: PPSMYAUEJRADFE-HXUWFJFHSA-N
in ch i: InChI=1S/C25H23F3N4O4/c1-15-5-6-18(14-30-15)36-17-4-2-3-16(11-17)12-22(33)32-10-9-29-24-19(20(32)13-23(34)35)7-8-21(31-24)25(26,27)28/h2-8,11,14,20H,9-10,12-13H2,1H3,(H,29,31)(H,34,35)/t20-/m1/s1
comment: Compound 9g is reported as a non-peptide, selective agonist of the bombesin BB3 receptor <Reference id=28346/>.
iupac name: 2-[(5R)-4-(2-{3-[(6-methylpyridin-3-yl)oxy]phenyl}acetyl)-8-(trifluoromethyl)-1H,2H,3H,4H,5H-pyrido[2,3-e][1,4]diazepin-5-yl]acetic acid
xref: CHEMBL3115390
approved: f
ligand name: compound 9g [PMID: 24412111]
type: SyntheticOrganicLigand

compound 9f [PMID: 24412111]
in ch i key: DFAPMGLBHDJMNX-LJQANCHMSA-N
in ch i: InChI=1S/C24H28F3N3O4/c1-15(2)8-11-34-17-5-3-4-16(12-17)13-21(31)30-10-9-28-23-18(19(30)14-22(32)33)6-7-20(29-23)24(25,26)27/h3-7,12,15,19H,8-11,13-14H2,1-2H3,(H,28,29)(H,32,33)/t19-/m1/s1
comment: Compound 9f is reported as a non-peptide, selective agonist of the bombesin BB3 receptor <Reference id=28346/>.
iupac name: 2-[(5R)-4-{2-[3-(3-methylbutoxy)phenyl]acetyl}-8-(trifluoromethyl)-1H,2H,3H,4H,5H-pyrido[2,3-e][1,4]diazepin-5-yl]acetic acid
approved: f
ligand name: compound 9f [PMID: 24412111]
type: SyntheticOrganicLigand

Elabela/Toddler-11
in ch i key: XXKPNJFJXZBRMX-HDKAIKTRSA-N
comment: Elabela/Toddler-11 is a predicted dibasic cleavage site isoform of <Ligand id=7930/>
approved: f
ligand name: Elabela/Toddler-11
type: PeptideLigand

Elabela/Toddler-21
in ch i key: TXSAAXFWNUKYQL-FMGZCOAKSA-N
comment: Elabela/Toddler-21 is a predicted dibasic cleavage site isoform of <Ligand id=7930/>
approved: f
ligand name: Elabela/Toddler-21
type: PeptideLigand

Elabela/Toddler-32
in ch i key: AXGBCVTUKUUUPN-PXWSXZDTSA-N
comment: Elabela/Toddler-32 is a predicted dibasic cleavage site isoform of <Ligand id=7930/>
approved: f
ligand name: Elabela/Toddler-32
type: PeptideLigand

MM07
in ch i key: RKFGCZWTURNFPN-SVENNQHVSA-N
comment: MM07, is a cyclic peptide agonist of the apelin receptor that is more stable than the endogenous apelin peptide. It acts as a biased agonist at the apelin receptor, that can preferentially stimulate the G protein pathway. It was hypothesised that this biased action could translate to improved efficacy in vitro by selectively stimulating vasodilatation and inotropic actions, whilst avoiding activation of detrimental β-arrestin-dependent pathways. We generated the HELM annotation and SMILES for MM07 using HELM Editor v1.4 (from Pistoia Alliance).
iupac name: L-cysteinyl-L-arginyl-L-prolyl-L-arginyl-L-leucyl-L-cysteinyl-L-histidyl-L-lysyl-glycyl-L-prolyl-L-methionyl-L-prolyl-L-phenylalanine (1->6)-disulfide
synonym: cyclo[1-6]CRPRLCHKGPMPF
approved: f
ligand name: MM07
type: PeptideLigand

PF-01247324
canonical SMILES: CNC(=O)c1ccc(c(n1)N)c1cc(Cl)cc(c1Cl)Cl
isomeric SMILES: CNC(=O)c1ccc(c(n1)N)c1cc(Cl)cc(c1Cl)Cl
in ch i key: HPIUHDCRVYDAEJ-UHFFFAOYSA-N
in ch i: InChI=1S/C13H10Cl3N3O/c1-18-13(20)10-3-2-7(12(17)19-10)8-4-6(14)5-9(15)11(8)16/h2-5H,1H3,(H2,17,19)(H,18,20)
comment: PF-01247324 is a NaV 1.8 blocker that attenuates nociception and sensory neuron excitability <Reference id=28442/>. This publication has an F1000 recommendation. There are six active analogues described in WO2006011050 but without quantitative data.
iupac name: 6-amino-N-methyl-5-(2,3,5-trichlorophenyl)pyridine-2-carboxamide
approved: f
ligand name: PF-01247324
type: SyntheticOrganicLigand

compound 58 [PMID: 25037917]
in ch i key: FNHAFYQTHUKPIU-UHFFFAOYSA-N
in ch i: InChI=1S/C23H21ClN4O/c24-19-4-1-3-18(13-19)16-5-7-17(8-6-16)22(29)28-20-9-10-21(28)15-27(14-20)23-25-11-2-12-26-23/h1-8,11-13,20-21H,9-10,14-15H2
comment: Compound 58 is reported as a selective inhibitor of SLC6A7, the sodium-dependent proline transporter (PROT) <Reference id=28424/>. Additional examples of acyl-piperazine based compounds with SAR data are reported in <Reference id=28424/>.
iupac name: 8-[4-(3-chlorophenyl)benzoyl]-3-(pyrimidin-2-yl)-3,8-diazabicyclo[3.2.1]octane
approved: f
ligand name: compound 58 [PMID: 25037917]
type: SyntheticOrganicLigand

PC-25
in ch i key: IRCKZEUJNJUYCC-UHFFFAOYSA-N
in ch i: InChI=1S/C21H24BrN7O3/c1-32-17-8-4-15(5-9-17)12-28-19(26-11-10-25-18(23)24)27-20(30)29(21(28)31)13-14-2-6-16(22)7-3-14/h2-9H,10-13H2,1H3,(H4,23,24,25)(H,26,27,30)
iupac name: 2-[2-[[5-[(4-bromophenyl)methyl]-1-[(4-methoxyphenyl)methyl]-4,6-dioxo-1,3,5-triazin-2-yl]amino]ethyl]guanidine
xref: CHEMBL3259533
synonym: traizine compound PC25
approved: f
ligand name: PC-25
type: SyntheticOrganicLigand

IS20
isomeric SMILES: COc1ccc(cc1)/C=C(/C(=O)NCc1cccnc1)/NC(=O)c1ccccc1
in ch i key: KKDANILRTKQMGA-STZFKDTASA-N
in ch i: InChI=1S/C23H21N3O3/c1-29-20-11-9-17(10-12-20)14-21(26-22(27)19-7-3-2-4-8-19)23(28)25-16-18-6-5-13-24-15-18/h2-15H,16H2,1H3,(H,25,28)(H,26,27)/b21-14-
iupac name: N-[(Z)-1-(4-methoxyphenyl)-3-oxo-3-(pyridin-3-ylmethylamino)prop-1-en-2-yl]benzamide
xref: CHEMBL1387323
approved: f
ligand name: IS20
type: SyntheticOrganicLigand

IS1
isomeric SMILES: O=C(/C(=C/c1ccco1)/NC(=O)c1ccccc1)NCc1cccnc1
in ch i key: ANTQNDKESCDJPE-PDGQHHTCSA-N
in ch i: InChI=1S/C20H17N3O3/c24-19(16-7-2-1-3-8-16)23-18(12-17-9-5-11-26-17)20(25)22-14-15-6-4-10-21-13-15/h1-13H,14H2,(H,22,25)(H,23,24)/b18-12-
iupac name: N-[(Z)-1-furan-2-yl-3-oxo-3-(pyridin-3-ylmethylamino)prop-1-en-2-yl]benzamide
xref: CHEMBL1499206
approved: f
ligand name: IS1
type: SyntheticOrganicLigand

MJN228
in ch i key: BLSWPPPBUQFKHH-UHFFFAOYSA-N
in ch i: InChI=1S/C20H20N4O3/c1-22-9-11-23(12-10-22)20(25)19-18(14-5-3-2-4-6-14)16-13-15(24(26)27)7-8-17(16)21-19/h2-8,13,21H,9-12H2,1H3
iupac name: (4-methylpiperazin-1-yl)-(5-nitro-3-phenyl-1H-indol-2-yl)methanone
approved: f
ligand name: MJN228
type: SyntheticOrganicLigand

MEA
canonical SMILES: CCCCCCCCCCCCCC(=O)NCCO
isomeric SMILES: CCCCCCCCCCCCCC(=O)NCCO
in ch i key: JHIXEZNTXMFXEK-UHFFFAOYSA-N
in ch i: InChI=1S/C16H33NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-16(19)17-14-15-18/h18H,2-15H2,1H3,(H,17,19)
iupac name: N-(2-hydroxyethyl)tetradecanamide
synonym: N-myristoylethanolamine
approved: f
ligand name: MEA
type: MetaboliteLigand

compound 17c [PMID: 25497965]
in ch i key: CJLZUKCACMUYFP-GOSISDBHSA-N
in ch i: InChI=1S/C24H26F3N3O5/c1-14(2)10-22(34)35-16-5-3-4-15(11-16)12-20(31)30-9-8-28-23-17(18(30)13-21(32)33)6-7-19(29-23)24(25,26)27/h3-7,11,14,18H,8-10,12-13H2,1-2H3,(H,28,29)(H,32,33)/t18-/m1/s1
comment: Compound 17c is reported as a selective, non-peptide agonist of the bombesin BB3 receptor <Reference id=28345/>.
iupac name: 2-[(5R)-4-(2-{3-[(3-methylbutanoyl)oxy]phenyl}acetyl)-8-(trifluoromethyl)-1H,2H,3H,4H,5H-pyrido[2,3-e][1,4]diazepin-5-yl]acetic acid
approved: f
ligand name: compound 17c [PMID: 25497965]
type: SyntheticOrganicLigand

[3H]bag-2
in ch i key: OENIXTHWZWFYIV-UHFFFAOYSA-N
in ch i: InChI=1S/C24H26N2O2/c27-24(28)22-8-4-3-7-21(22)19-12-9-17(10-13-19)11-14-23-25-16-20(26-23)15-18-5-1-2-6-18/h3-4,7-10,12-13,16,18H,1-2,5-6,11,14-15H2,(H,25,26)(H,27,28)
comment: Bag-2 is a non-peptide agonist of the bombesin BB3 receptor. The name provided for this tritiated version of the compound in the originating article is 4'-{2-[5-(cyclopentyl-methyl)-1H-imidazol-2-yl]-1,2-ditritium-ethyl}biphenyl-2-carboxylic acid <Reference id=20722/>. We show the structure for the un-labelled molecule, without specifying location of the tritium atoms. See the <Ligand id=6189/> page for further details about this ligand.
iupac name: 2-[4-[2-[5-(cyclopentylmethyl)-1H-imidazol-2-yl]ethyl]phenyl]benzoic acid
xref: CHEMBL1084942
approved: f
ligand name: [3H]bag-2
type: SyntheticOrganicLigand

ML-18
in ch i key: JOKVJNCYOSFDGC-LJAQVGFWSA-N
in ch i: InChI=1S/C32H35N5O5/c1-42-26-15-9-23(10-16-26)32(17-5-2-6-18-32)21-34-30(38)29(19-22-20-33-28-8-4-3-7-27(22)28)36-31(39)35-24-11-13-25(14-12-24)37(40)41/h3-4,7-16,20,29,33H,2,5-6,17-19,21H2,1H3,(H,34,38)(H2,35,36,39)/t29-/m0/s1
comment: ML-18 is reported as a non-peptide antagonist of the bombesin BB3 receptor <Reference id=28344/>.
iupac name: (2S)-3-(1H-indol-3-yl)-N-{[1-(4-methoxyphenyl)cyclohexyl]methyl}-2-{[(4-nitrophenyl)carbamoyl]amino}propanamide
approved: f
ligand name: ML-18
type: SyntheticOrganicLigand

compound 22e [PMID: 20167483]
in ch i key: AXHVEQQLKVIZLO-UHFFFAOYSA-N
in ch i: InChI=1S/C24H28N2O2/c1-4-24(2,3)15-19-16-25-22(26-19)14-11-17-9-12-18(13-10-17)20-7-5-6-8-21(20)23(27)28/h5-10,12-13,16H,4,11,14-15H2,1-3H3,(H,25,26)(H,27,28)
comment: Compound 22e is reported as a non-peptide agonist of the BB3 receptor <Reference id=20717/>.
iupac name: 2-[4-[2-[5-(2,2-dimethylbutyl)-1H-imidazol-2-yl]ethyl]phenyl]benzoic acid
xref: CHEMBL1089721
approved: f
ligand name: compound 22e [PMID: 20167483]
type: SyntheticOrganicLigand

compound 8a [PMID: 24900283]
in ch i key: OAIVSBLLDFJYMS-UHFFFAOYSA-N
comment: Compound 8a is reported as a non-peptide agonist of the BB3 receptor <Reference id=28343/>.
iupac name: 6-(4-tert-butylphenyl)sulfonyl-7,8-dimethyl-2-(trifluoromethyl)-5,11-dihydropyrido[3,2-c][1,5]benzodiazepine
xref: CHEMBL2164575
approved: f
ligand name: compound 8a [PMID: 24900283]
type: SyntheticOrganicLigand

droxidopa
canonical SMILES: OC(=O)C(C(c1ccc(c(c1)O)O)O)N
isomeric SMILES: OC(=O)[C@H]([C@@H](c1ccc(c(c1)O)O)O)N
in ch i key: QXWYKJLNLSIPIN-JGVFFNPUSA-N
in ch i: InChI=1S/C9H11NO5/c10-7(9(14)15)8(13)4-1-2-5(11)6(12)3-4/h1-3,7-8,11-13H,10H2,(H,14,15)/t7-,8+/m0/s1
comment: As droxidopa is a prodrug for noradrenaline, its effects will be through noradrenaline activation of adrenoceptors. The cellular effect is dependent upon adrenoceptor subtype expression on target cells.
iupac name: (2S,3R)-2-amino-3-(3,4-dihydroxyphenyl)-3-hydroxypropanoic acid
xref: CHEMBL2103827
synonym: L-DOPS
synonym: SM-5688
synonym: Northera®
approved: t
ligand name: droxidopa
type: SyntheticOrganicLigand

MK-7725
in ch i key: WQQNCCUPGPFWOI-UHFFFAOYSA-N
comment: MK-7725 is reported as a selective non-peptide agonist of the BB3 receptor <Reference id=28342/>.
iupac name: 2-[3-[6-[4-(trifluoromethoxy)phenyl]sulfonyl-2-(trifluoromethyl)-5,11-dihydropyrido[3,2-c][1,5]benzodiazepin-7-yl]-1,2,4-oxadiazol-5-yl]propan-2-ol
xref: CHEMBL2023109
synonym: MK7725
synonym: MK 7725
approved: f
ligand name: MK-7725
type: SyntheticOrganicLigand

SX-517
in ch i key: VZRIHFZJVIOJBE-UHFFFAOYSA-N
comment: SX-517 is reported as an antagonist of the CXCR1 and CXCR2 cytokine receptors <Reference id=28316/>.
iupac name: [2-[[5-[(4-fluorophenyl)carbamoyl]pyridin-2-yl]sulfanylmethyl]phenyl]boronic acid
approved: f
ligand name: SX-517
type: SyntheticOrganicLigand

danirixin
in ch i key: NGYNBSHYFOFVLS-LBPRGKRZSA-N
comment: Danirixin (GSK-1325756B) is being developed as a clinically efficacious antagonist of the CXCR2 chemokine receptor <Reference id=28315/>.
iupac name: 1-[4-chloro-2-hydroxy-3-[(3S)-piperidin-3-yl]sulfonylphenyl]-3-(3-fluoro-2-methylphenyl)urea
xref: CHEMBL3039531
synonym: GSK-1325756B
synonym: GSK1325756B
synonym: GSK 1325756B
synonym: GSK1325756
approved: f
ligand name: danirixin
type: SyntheticOrganicLigand

elubirixin
in ch i key: YQYFEGTYCUQBEI-UHFFFAOYSA-N
comment: Elubirixin (SB-656933) is reported as a CXCR2 selective antagonist <Reference id=28313/><Reference id=23884/>.
iupac name: 3-(2-chloro-3-fluorophenyl)-1-(4-chloro-2-hydroxy-3-piperazin-1-ylsulfonylphenyl)urea
xref: CHEMBL2178579
synonym: SB-656933
synonym: SB656933
synonym: SB 656933
approved: f
ligand name: elubirixin
type: SyntheticOrganicLigand

reparixin
canonical SMILES: CC(Cc1ccc(cc1)C(C(=O)NS(=O)(=O)C)C)C
in ch i key: KQDRVXQXKZXMHP-LLVKDONJSA-N
in ch i: InChI=1S/C14H21NO3S/c1-10(2)9-12-5-7-13(8-6-12)11(3)14(16)15-19(4,17)18/h5-8,10-11H,9H2,1-4H3,(H,15,16)/t11-/m1/s1
comment: Reparixin is an orally bioavailable compound that has been explored for potential to disrupt IL-8/CXCR1/2 signalling in cancer and transplant indications. It negatively modulates CXCR1 and CXCR2 dependent functions <Reference id=2311/>, but without inhibiting chemokine binding to either receptor. Direct binding to CXCR1 has only been indicated by molecular modelling, so the mechanism of action of this molecule remains to be fully resolved.
iupac name: (2R)-2-[4-(2-methylpropyl)phenyl]-N-methylsulfonylpropanamide
xref: CHEMBL191413
synonym: repertaxin
synonym: DF 1681Y
approved: f
ligand name: reparixin
type: SyntheticOrganicLigand

navarixin
in ch i key: RXIUEIPPLAFSDF-CYBMUJFWSA-N
in ch i: InChI=1S/C21H23N3O5/c1-5-13(15-10-9-11(2)29-15)22-16-17(20(27)19(16)26)23-14-8-6-7-12(18(14)25)21(28)24(3)4/h6-10,13,22-23,25H,5H2,1-4H3/t13-/m1/s1
comment: Navarixin (SCH-527123, MK-7123) is a potent and orally bioavailable CXCR2/CXCR1 receptor antagonist <Reference id=28288/>.
iupac name: 2-hydroxy-N,N-dimethyl-3-[[2-[[(1R)-1-(5-methylfuran-2-yl)propyl]amino]-3,4-dioxo-1-cyclobutenyl]amino]benzamide
xref: CHEMBL216981
synonym: SCH527123
synonym: SCH 527123
synonym: SCH-527123
synonym: MK-7123
synonym: MK7123
approved: f
ligand name: navarixin
type: SyntheticOrganicLigand

niclosamide
canonical SMILES: Clc1ccc(c(c1)C(=O)Nc1ccc(cc1Cl)[N+](=O)[O-])O
isomeric SMILES: Clc1ccc(c(c1)C(=O)Nc1ccc(cc1Cl)[N+](=O)[O-])O
in ch i key: RJMUSRYZPJIFPJ-UHFFFAOYSA-N
in ch i: InChI=1S/C13H8Cl2N2O4/c14-7-1-4-12(18)9(5-7)13(19)16-11-3-2-8(17(20)21)6-10(11)15/h1-6,18H,(H,16,19)
comment: STAT3 inhibitor; inhibits mTORC1 signaling; positive allosteric modulator (PAM) of the neuropeptide Y4 receptor <Reference id=32270/>. Evidence from repurposing studies suggests some activity against methicillin-resistant Staphylococcus aureus (MRSA), and Zika virus (in vitro) <Reference id=32271/>.
iupac name: 5-Chloro-N-(2-chloro-4-nitrophenyl)-2-hydroxybenzamide
synonym: VU0243604
approved: t
ligand name: niclosamide
type: SyntheticOrganicLigand

compound 11 [PMID: 16413183]
isomeric SMILES: OC(=O)CC(C1=C/C(=c/2/[nH]c3c([nH]2)ccc(c3)C(=N)N)/C(=O)C(=C1)c1cccc(c1)C(=O)N)C(=O)O
in ch i key: WFPGMUDIBWJJND-JJIBRWJFSA-N
in ch i: InChI=1S/C25H21N5O6/c26-22(27)12-4-5-18-19(9-12)30-24(29-18)17-8-14(16(25(35)36)10-20(31)32)7-15(21(17)33)11-2-1-3-13(6-11)23(28)34/h1-9,16,29-30H,10H2,(H3,26,27)(H2,28,34)(H,31,32)(H,35,36)/b24-17+
comment: Compound 11 is reported as a small molecule inhibitor of plasma kallikrein (KLKB1) <Reference id=28272/>. Compound 11 exhibits favourable pharmacokinetics in rats and may have potential therapeutic uses in inflammatory or coagulation disorders.
iupac name: 2-[(3E)-3-(5-carbamimidoyl-1,3-dihydrobenzimidazol-2-ylidene)-5-(3-carbamoylphenyl)-4-oxocyclohexa-1,5-dien-1-yl]butanedioic acid
xref: CHEMBL206454
approved: f
ligand name: compound 11 [PMID: 16413183]
type: SyntheticOrganicLigand

SKA-121
canonical SMILES: Nc1nc2c(o1)c1ccccc1c(c2)C
isomeric SMILES: Nc1nc2c(o1)c1ccccc1c(c2)C
in ch i key: JEGUERWMMMQFJV-UHFFFAOYSA-N
in ch i: InChI=1S/C12H10N2O/c1-7-6-10-11(15-12(13)14-10)9-5-3-2-4-8(7)9/h2-6H,1H3,(H2,13,14)
comment: SKA-121 has been shown to be a KCa3.1-specific positive gating modulator suitable for further exploring the therapeutic potential of KCa3.1 activation <Reference id=28271/>.
iupac name: 5-methylnaphtho[2,1-d]oxazol-2-amine
synonym: SKA121
synonym: SKA 121
approved: f
ligand name: SKA-121
type: SyntheticOrganicLigand

compound 8 [PMID: 21692504]
canonical SMILES: N#Cc1c(=O)[nH]c(c2c1CCC2)CC(C)C
isomeric SMILES: N#Cc1c(=O)[nH]c(c2c1CCC2)CC(C)C
in ch i key: QOUMCRXJXXVERM-UHFFFAOYSA-N
in ch i: InChI=1S/C13H16N2O/c1-8(2)6-12-10-5-3-4-9(10)11(7-14)13(16)15-12/h8H,3-6H2,1-2H3,(H,15,16)
comment: Compound 8 is reported as a brain-penetrating inhibitor of prolyl endopeptidase-like (PREPL) enzyme activity <Reference id=28270/>. Compound 8 is a useful pharmacological tool for investigating the biochemistry and physiological function of PREPL.
iupac name: 1-(2-methylpropyl)-3-oxo-2,5,6,7-tetrahydrocyclopenta[d]pyridine-4-carbonitrile
xref: CHEMBL1341461
approved: f
ligand name: compound 8 [PMID: 21692504]
type: SyntheticOrganicLigand

cytosine
canonical SMILES: Nc1ccnc(=O)[nH]1
isomeric SMILES: Nc1ccnc(=O)[nH]1
in ch i key: OPTASPLRGRRNAP-UHFFFAOYSA-N
in ch i: InChI=1S/C4H5N3O/c5-3-1-2-6-4(8)7-3/h1-2H,(H3,5,6,7,8)
iupac name: 4-amino-3H-pyrimidin-2-one
xref: ChEMBL15913
approved: f
ligand name: cytosine
type: MetaboliteLigand

aminooxyacetic acid
canonical SMILES: NOCC(=O)O
isomeric SMILES: NOCC(=O)O
in ch i key: NQRKYASMKDDGHT-UHFFFAOYSA-N
in ch i: InChI=1S/C2H5NO3/c3-6-1-2(4)5/h1,3H2,(H,4,5)
iupac name: 2-(aminooxy)acetic acid
xref: CHEMBL347862
synonym: carboxymethoxylamine
synonym: AOAA
approved: f
ligand name: aminooxyacetic acid
type: MetaboliteLigand

example 131 [WO2009133348]
in ch i key: ALLYUHIQZKTLFG-RBUKOAKNSA-N
in ch i: InChI=1S/C22H27F2N5O2/c1-2-29-9-3-4-19(29)22(31)28-18(11-14-5-7-16(23)17(24)10-14)21(30)27-13-15-6-8-20(25)26-12-15/h5-8,10,12,18-19H,2-4,9,11,13H2,1H3,(H2,25,26)(H,27,30)(H,28,31)/t18-,19+/m0/s1
comment: This compound is claimed in patent WO2009133348 <Reference id=28237/>. WO2009133348 reports the development of human tissue kallikrein (KLK1) inhibitors, and covers their use for the treatment of conditions such as asthma and chronic obstructive pulmonary disease (COPD).
iupac name: (2R)-N-[(2S)-1-[(6-aminopyridin-3-yl)methylamino]-3-(3,4-difluorophenyl)-1-oxopropan-2-yl]-1-ethylpyrrolidine-2-carboxamide
approved: f
ligand name: example 131 [WO2009133348]
type: SyntheticOrganicLigand

compound 3 [PMID: 23849879]
canonical SMILES: Cc1ccc(cc1)C(=O)n1nc(nc1N)c1cccnc1
isomeric SMILES: Cc1ccc(cc1)C(=O)n1nc(nc1N)c1cccnc1
in ch i key: BIEYFOHSWAIQDF-UHFFFAOYSA-N
in ch i: InChI=1S/C15H13N5O/c1-10-4-6-11(7-5-10)14(21)20-15(16)18-13(19-20)12-3-2-8-17-9-12/h2-9H,1H3,(H2,16,18,19)
comment: Compound 3 is a nonpeptide, reversible inhibitor of human kallikrein proteins <Reference id=28235/>. Small molecule inhibitors of human kallikreins 5, 7 and 14 are being developed with the aim of pharmacologically controlling unopposed proteolytic cascades in skin diseases such as Netherton syndrome <Reference id=28235/>.
iupac name: (5-amino-3-pyridin-3-yl-1,2,4-triazol-1-yl)-(4-methylphenyl)methanone
xref: CHEMBL1413622
approved: f
ligand name: compound 3 [PMID: 23849879]
type: SyntheticOrganicLigand

veldoreotide
in ch i key: ABFNTRQPWNXUHA-VEVJRHMJSA-N
in ch i: InChI=1S/C60H74N12O10/c1-37(73)54-59(81)70-50(31-39-18-6-3-7-19-39)60(82)72(36-51(62)74)29-15-26-52(75)63-28-14-25-53(76)66-47(30-38-16-4-2-5-17-38)56(78)68-49(33-41-35-65-45-23-11-9-21-43(41)45)58(80)69-48(32-40-34-64-44-22-10-8-20-42(40)44)57(79)67-46(55(77)71-54)24-12-13-27-61/h2-11,16-23,34-35,37,46-50,54,64-65,73H,12-15,24-33,36,61H2,1H3,(H2,62,74)(H,63,75)(H,66,76)(H,67,79)(H,68,78)(H,69,80)(H,70,81)(H,71,77)/t37-,46+,47+,48-,49+,50+,54+/m1/s1
comment: Veldoreotide (COR-005) is an investigational somatostatin analogue (SSA) <Reference id=32234/> in early stage development for treatment of patients with acromegaly.
iupac name: 2-[(3S,6S,9S,12R,15S,18S)-9-(4-aminobutyl)-6-(1-hydroxyethyl)-12,15-bis(1H-indol-3-ylmethyl)-2,5,8,11,14,17,20,25-octaoxo-3,18-bis(phenylmethyl)-1,4,7,10,13,16,19,24-octazacyclooctacos-1-yl]acetamide
synonym: PTR-3173
synonym: DG3173
synonym: somatoprim
synonym: COR-005
approved: f
ligand name: veldoreotide
type: PeptideLigand

compound 10 [PMID: 19402633]
in ch i key: AKSIZPIFQAYJGF-UHFFFAOYSA-N
comment: Compound 10 [PMID 19402633] is a highly seelctive inhibitor of Aurora kinase A compared to Aurora kinase B (1000-fold selective) <Reference id=28157/>.
iupac name: N-(2-chlorophenyl)-4-[[2-[4-[2-(4-ethylpiperazin-1-yl)-2-oxoethyl]anilino]-5-fluoropyrimidin-4-yl]amino]benzamide
xref: CHEMBL502124
synonym: Aurora A inhibitor I
synonym: 2,4-Bisanilinopyrimidine, 10
approved: f
ligand name: compound 10 [PMID: 19402633]
type: SyntheticOrganicLigand

compound 20 [PMID: 23692593]
in ch i key: AKGOAAVLALZKCN-JSLVBRCRSA-N
comment: This compound is reported as an inhibitor of the serine protease activity of prostate-specific antigen (PSA, aka kallikrein-related peptidase 3) <Reference id=28232/>.
iupac name: [(1S)-1-[[(2S)-2-[[(2S)-5-amino-2-[[(2S)-2-[[(2S)-2-(6-aminohexanoylamino)-3-phenylpropanoyl]amino]-3-hydroxypropanoyl]amino]-5-oxopentanoyl]amino]hexanoyl]amino]-4-bromobutyl]boronic acid
xref: CHEMBL2381669
synonym: Ahx-FSQn(boro)Bpg
approved: f
ligand name: compound 20 [PMID: 23692593]
type: SyntheticOrganicLigand

compound 48 [PMID: 25815140]
in ch i key: YJLIKUSWRSEPSM-WGQQHEPDSA-N
in ch i: InChI=1S/C23H24N6O4/c24-20-17-21(27-12-26-20)29(22-19(32)18(31)16(11-30)33-22)23(28-17)25-10-13-6-8-15(9-7-13)14-4-2-1-3-5-14/h1-9,12,16,18-19,22,30-32H,10-11H2,(H,25,28)(H2,24,26,27)/t16-,18-,19-,22-/m1/s1
comment: Compound 48 is an 8-aminoadenosine derivative reported as a novel inhibitor of the human sodium/nucleoside cotransporter 2 (CNT2, gene symbol SLC28A2) <Reference id=28230/>. As 'Example 54' this compound is protected by patent US20070179115 <Reference id=28231/>.
iupac name: (2R,3R,4S,5R)-2-[6-amino-8-[(4-phenylphenyl)methylamino]purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol
approved: f
ligand name: compound 48 [PMID: 25815140]
type: SyntheticOrganicLigand

compound 4d [PMID: 25489658]
in ch i key: RNWNTBMGGUARMR-UHFFFAOYSA-N
in ch i: InChI=1S/C17H10BrClO4/c18-9-10-4-5-15-11(6-10)7-14(17(21)23-15)16(20)22-13-3-1-2-12(19)8-13/h1-8H,9H2
comment: Compound 4d is reported as an irreversible, non-peptide inhibitor of kallikrein proteins <Reference id=28216/>. This compound appears to be patent protected by US-9006466-B2 <Reference id=28217/>.
iupac name: (3-chlorophenyl) 6-(bromomethyl)-2-oxochromene-3-carboxylate
approved: f
ligand name: compound 4d [PMID: 25489658]
type: SyntheticOrganicLigand

decynium 22
canonical SMILES: CC[n+]1c(ccc2c1cccc2)C=c1ccc2c(n1CC)cccc2
isomeric SMILES: CC[n+]1c(ccc2c1cccc2)C=c1ccc2c(n1CC)cccc2
in ch i key: AGJZCWVTGOVGBS-UHFFFAOYSA-N
in ch i: InChI=1S/C23H23N2/c1-3-24-20(15-13-18-9-5-7-11-22(18)24)17-21-16-14-19-10-6-8-12-23(19)25(21)4-2/h5-17H,3-4H2,1-2H3/q+1
comment: Decynium 22 is a potent inhibitor of the plasma membrane monoamine transporter (PMAT aka NET4; SLC29A4) <Reference id=28215/>. It is also reported to inhibit the organic action transporter OCT2 (SLC22A2) <Reference id=17635/>. Strictly, decynium 22 refers to the iodide salt (PubChem CID 5484462), but we show the parent molecule in this ligand entry.
xref: CHEMBL1197556
synonym: Dy22
synonym: 1,1'-diethyl-2,2'-cyanine
synonym: NSC-97374
synonym: GNF-Pf-1919
synonym: GNF-Pf-4440
synonym: decynium-22
synonym: D-22
synonym: pseudoisocyanine
approved: f
ligand name: decynium 22
type: SyntheticOrganicLigand

LDN-214117
in ch i key: BHUXVRVMMYAXKN-UHFFFAOYSA-N
in ch i: InChI=1S/C25H29N3O3/c1-17-22(19-14-23(29-2)25(31-4)24(15-19)30-3)13-20(16-27-17)18-5-7-21(8-6-18)28-11-9-26-10-12-28/h5-8,13-16,26H,9-12H2,1-4H3
comment: LDN-214117 is an experimental activin A receptor, type I (ACVR1 aka BMP type I receptor kinase ALK2) inhibitor <Reference id=28206/>. LDN-214117 may provide a structural template for the preclinical development of novel therapeutics for conditions such as fibrodysplasia ossificans progressiva (FOP), characterised by inappropriate BMP signalling, and reported to be caused by gain-of-function ALK2 mutations <Reference id=28207/><Reference id=28208/><Reference id=28209/><Reference id=28210/>.
iupac name: 1-[4-[6-methyl-5-(3,4,5-trimethoxyphenyl)pyridin-3-yl]phenyl]piperazine
xref: CHEMBL3341789
synonym: compound 10 [PMID: 25101911]
synonym: LDN214117
approved: f
ligand name: LDN-214117
type: SyntheticOrganicLigand

phenylbutyrate
canonical SMILES: OC(=O)CCCc1ccccc1
isomeric SMILES: OC(=O)CCCc1ccccc1
in ch i key: OBKXEAXTFZPCHS-UHFFFAOYSA-N
in ch i: InChI=1S/C10H12O2/c11-10(12)8-4-7-9-5-2-1-3-6-9/h1-3,5-6H,4,7-8H2,(H,11,12)
comment: The salt, sodium phenylbutyrate (PubChem CID 5258) is an inhibitor of histone deacetylase (HDAC) activity <Reference id=28204/><Reference id=28203/>.
iupac name: 4-Phenylbutanoic acid
xref: CHEMBL1469
synonym: gamma-phenylbutyric acid
synonym: 4-phenylbutanoic acid
synonym: Buphenyl®
synonym: Ammonaps®
synonym: triButyrate
approved: t
ligand name: phenylbutyrate
type: SyntheticOrganicLigand

AZD2858
in ch i key: FHCSBLWRGCOVPT-UHFFFAOYSA-N
in ch i: InChI=1S/C21H23N7O3S/c1-27-9-11-28(12-10-27)32(30,31)17-6-4-15(5-7-17)18-14-24-20(22)19(26-18)21(29)25-16-3-2-8-23-13-16/h2-8,13-14H,9-12H2,1H3,(H2,22,24)(H,25,29)
comment: AZD2858 is an orally active inhibitor of glycogen synthase kinase 3 beta (GSK-3β) <Reference id=28200/>.
iupac name: 3-amino-6-[4-(4-methylpiperazin-1-yl)sulfonylphenyl]-N-pyridin-3-ylpyrazine-2-carboxamide
xref: CHEMBL2177161
synonym: AZD 2858
synonym: AZD-2858
synonym: compound 18 [PMID: 22489897]
approved: f
ligand name: AZD2858
type: SyntheticOrganicLigand

AZ20
in ch i key: SCGCBAAYLFTIJU-CQSZACIVSA-N
in ch i: InChI=1S/C21H24N4O3S/c1-14-13-28-11-10-25(14)19-12-18(21(7-8-21)29(2,26)27)23-20(24-19)16-4-3-5-17-15(16)6-9-22-17/h3-6,9,12,14,22H,7-8,10-11,13H2,1-2H3/t14-/m1/s1
comment: AZ20 is a novel potent and selective inhibitor the ATR serine/threonine kinase (ATR) <Reference id=28198/>.
iupac name: (3R)-4-[2-(1H-indol-4-yl)-6-(1-methylsulfonylcyclopropyl)pyrimidin-4-yl]-3-methylmorpholine
xref: CHEMBL2325697
synonym: AZ-20
synonym: AZ 20
synonym: compound 6 [PMID: 46244454]
approved: f
ligand name: AZ20
type: SyntheticOrganicLigand

AZ960
in ch i key: SUNXHXDJOIXABJ-NSHDSACASA-N
in ch i: InChI=1S/C18H16F2N6/c1-10-7-16(26-25-10)23-18-15(20)8-13(9-21)17(24-18)22-11(2)12-3-5-14(19)6-4-12/h3-8,11H,1-2H3,(H3,22,23,24,25,26)/t11-/m0/s1
comment: AZ960 is a novel ATP competitive Janus kinase 2 (JAK2) inhibitor <Reference id=23541/>.
iupac name: 5-fluoro-2-[[(1S)-1-(4-fluorophenyl)ethyl]amino]-6-[(5-methyl-1H-pyrazol-3-yl)amino]pyridine-3-carbonitrile
xref: CHEMBL1774055
synonym: AZ 960
synonym: AZ-960
approved: f
ligand name: AZ960
type: SyntheticOrganicLigand

AZ628
in ch i key: ZGBGPEDJXCYQPH-UHFFFAOYSA-N
in ch i: InChI=1S/C27H25N5O2/c1-17-8-9-21(31-25(33)18-6-5-7-19(12-18)27(2,3)15-28)14-24(17)30-20-10-11-23-22(13-20)26(34)32(4)16-29-23/h5-14,16,30H,1-4H3,(H,31,33)
comment: AZ628 is an experimental inhibitor of RAF kinases <Reference id=28193/>. Preclinical data for AZ628 was presented at the AACR Annual Meeting by Shen et al. in 2007 (Linking molecular characteristics to the pharmacological response of a panel of cancer cell lines to the BRAF inhibitor, AZ628).
iupac name: 3-(2-cyanopropan-2-yl)-N-[4-methyl-3-[(3-methyl-4-oxoquinazolin-6-yl)amino]phenyl]benzamide
xref: CHEMBL2144069
synonym: AZ 628
synonym: AZ-628
approved: f
ligand name: AZ628
type: SyntheticOrganicLigand

AZD8330
in ch i key: RWEVIPRMPFNTLO-UHFFFAOYSA-N
in ch i: InChI=1S/C16H17FIN3O4/c1-9-7-11(15(23)20-25-6-5-22)14(21(2)16(9)24)19-13-4-3-10(18)8-12(13)17/h3-4,7-8,19,22H,5-6H2,1-2H3,(H,20,23)
comment: AZD8330 is a non-ATP competitive inhibitor of the kinases MEK 1 and MEK2. Clinical development was terminated at Phase 1.
iupac name: 2-[(2-fluoro-4-iodophenyl)amino]-N-(2-hydroxyethoxy)-1,5-dimethyl-6-oxopyridine-3-carboxamide
xref: CHEMBL3182621
synonym: AZD-8330
synonym: ARRY-704
synonym: ARRY 704
synonym: ARRY704
synonym: ARRY-424704
synonym: ARRY 424704
synonym: ARRY424704
synonym: AZD 8330
approved: f
ligand name: AZD8330
type: SyntheticOrganicLigand

aminoguanidine
canonical SMILES: NNC(=N)N
isomeric SMILES: NNC(=N)N
in ch i key: HAMNKKUPIHEESI-UHFFFAOYSA-N
in ch i: InChI=1S/CH6N4/c2-1(3)5-4/h4H2,(H4,2,3,5)
iupac name: 1-aminoguanidine
xref: CHEMBL225304
synonym: pimagedine
synonym: amino guanidine
approved: f
ligand name: aminoguanidine
type: MetaboliteLigand

AZD2461
in ch i key: HYNBNUYQTQIHJK-UHFFFAOYSA-N
in ch i: InChI=1S/C22H22FN3O3/c1-29-15-8-10-26(11-9-15)22(28)18-12-14(6-7-19(18)23)13-20-16-4-2-3-5-17(16)21(27)25-24-20/h2-7,12,15H,8-11,13H2,1H3,(H,25,27)
comment: AZD2461 is an inhibitor of poly(ADP-ribose)polymerase (PARP) enzymes. AZD2461 is compound 2b in patent WO2009093032 A1 <Reference id=28187/>.
iupac name: 4-[[4-fluoro-3-(4-methoxypiperidine-1-carbonyl)phenyl]methyl]-2H-phthalazin-1-one
synonym: AZD-2461
synonym: AZD 2461
approved: f
ligand name: AZD2461
type: SyntheticOrganicLigand

GSK256073
canonical SMILES: CCCCCn1c(=O)[nH]c(=O)c2c1nc([nH]2)Cl
isomeric SMILES: CCCCCn1c(=O)[nH]c(=O)c2c1nc([nH]2)Cl
in ch i key: CGAMDQCXAAOFSR-UHFFFAOYSA-N
in ch i: InChI=1S/C10H13ClN4O2/c1-2-3-4-5-15-7-6(12-9(11)13-7)8(16)14-10(15)17/h2-5H2,1H3,(H,12,13)(H,14,16,17)
iupac name: 8-chloro-3-pentyl-7H-purine-2,6-dione
synonym: GSK-256073
synonym: GSK 256073
approved: f
ligand name: GSK256073
type: SyntheticOrganicLigand

SCH 900271
in ch i key: ARJKMWXLIHZLQZ-UHFFFAOYSA-N
in ch i: InChI=1S/C14H16N2O4/c1-14(5-6-14)4-2-3-8-7-9(17)20-12-10(8)11(18)15-13(19)16-12/h7H,2-6H2,1H3,(H2,15,16,18,19)
iupac name: 5-[3-(1-Methylcyclopropyl)propyl]-2H-pyrano[2,3-d]pyrimidine-2,4,7(1H,3H)-trione
synonym: SCH900271
approved: f
ligand name: SCH 900271
type: SyntheticOrganicLigand

ME0328
in ch i key: QIHBWVVVRYYYRO-ZDUSSCGKSA-N
in ch i: InChI=1S/C19H19N3O2/c1-13(14-7-3-2-4-8-14)20-18(23)12-11-17-21-16-10-6-5-9-15(16)19(24)22-17/h2-10,13H,11-12H2,1H3,(H,20,23)(H,21,22,24)/t13-/m0/s1
comment: ME0328 is an experimental probe compound which selectively inhibits the activity of poly (ADP-ribose) polymerase 3 (PARP3) <Reference id=28162/>.
iupac name: 3-(4-oxo-1H-quinazolin-2-yl)-N-[(1S)-1-phenylethyl]propanamide
xref: CHEMBL3092537
synonym: ME-0328
synonym: compound 5b [PMID 24188023]
approved: f
ligand name: ME0328
type: SyntheticOrganicLigand

compound 2 [PMID: 24486398]
in ch i key: ZLQAEANISSHOLB-WKILWMFISA-N
in ch i: InChI=1S/C22H30N4O2S2/c1-15-5-7-16(8-6-15)21(28)24-22-23-20(17-4-3-13-29-17)18(30-22)14-19(27)26-11-9-25(2)10-12-26/h3-4,13,15-16H,5-12,14H2,1-2H3,(H,23,24,28)/t15-,16-
comment: This ligand is represented in PubChem by CID 86279608, which does not include any chiral specification.
iupac name: 4-methyl-N-[5-[2-(4-methylpiperazin-1-yl)-2-oxoethyl]-4-thiophen-2-yl-1,3-thiazol-2-yl]cyclohexane-1-carboxamide
approved: f
ligand name: compound 2 [PMID: 24486398]
type: SyntheticOrganicLigand

compound 31 [PMID: 24809814]
in ch i key: XUZUIICAPXZZDU-GOSISDBHSA-N
in ch i: InChI=1S/C26H23ClN6/c1-18-17-32(11-12-33(18)25-10-7-20(15-28)16-29-25)26-23-14-21(27)8-9-22(23)24(30-31-26)13-19-5-3-2-4-6-19/h2-10,14,16,18H,11-13,17H2,1H3/t18-/m1/s1
iupac name: 6-[(2R)-4-(4-benzyl-7-chlorophthalazin-1-yl)-2-methylpiperazin-1-yl]pyridine-3-carbonitrile
xref: CHEMBL3290331
synonym: compound 31 [PMID: 24809814]
approved: f
ligand name: compound 31 [PMID: 24809814]
type: SyntheticOrganicLigand

droxinostat
canonical SMILES: ONC(=O)CCCOc1ccc(cc1C)Cl
isomeric SMILES: ONC(=O)CCCOc1ccc(cc1C)Cl
in ch i key: JHSXDAWGLCZYSM-UHFFFAOYSA-N
in ch i: InChI=1S/C11H14ClNO3/c1-8-7-9(12)4-5-10(8)16-6-2-3-11(14)13-15/h4-5,7,15H,2-3,6H2,1H3,(H,13,14)
comment: Droxinostat is a selective inhibitor of histone deacetylases (HDACs) 3, 6 and 8 <Reference id=28154/>.
iupac name: 4-(4-Chloro-2-methylphenoxy)-N-hydroxybutanamide
xref: CHEMBL1526649
synonym: NS-41080
synonym: NS41080
approved: f
ligand name: droxinostat
type: SyntheticOrganicLigand

amelubant
in ch i key: SBVYURPQULDJTI-UHFFFAOYSA-N
in ch i: InChI=1S/C33H34N2O5/c1-4-38-32(37)35-31(34)25-8-16-29(17-9-25)39-21-23-6-5-7-24(20-23)22-40-30-18-12-27(13-19-30)33(2,3)26-10-14-28(36)15-11-26/h5-20,36H,4,21-22H2,1-3H3,(H2,34,35,37)
comment: Amebulant is a leukotriene B4 (BLT1) receptor antagonist prodrug <Reference id=20674/>.
iupac name: ethyl (NZ)-N-[amino-[4-[[3-[[4-[2-(4-hydroxyphenyl)propan-2-yl]phenoxy]methyl]phenyl]methoxy]phenyl]methylidene]carbamate
synonym: BIIL 284
synonym: BIIL-284
approved: f
ligand name: amelubant
type: SyntheticOrganicLigand

AH 11110
canonical SMILES: OC(CC(=N)N1CCCCC1)COc1ccccc1c1ccccc1.Cl
isomeric SMILES: OC(CC(=N)N1CCCCC1)COc1ccccc1c1ccccc1.Cl
in ch i key: WWHGFIXWBLHHQB-UHFFFAOYSA-N
in ch i: InChI=1S/C21H26N2O2.ClH/c22-21(23-13-7-2-8-14-23)15-18(24)16-25-20-12-6-5-11-19(20)17-9-3-1-4-10-17;/h1,3-6,9-12,18,22,24H,2,7-8,13-16H2;1H
iupac name: 4-imino-1-(2-phenylphenoxy)-4-piperidin-1-ylbutan-2-ol hydrochloride
synonym: AH11110
synonym: AH-11110
approved: f
ligand name: AH 11110
type: SyntheticOrganicLigand

Rec 15/2615
in ch i key: ZZMFJJDBKSYGRM-UHFFFAOYSA-N
in ch i: InChI=1S/C26H33N5O5/c1-16(2)17-7-6-8-20(33-3)24(17)36-15-23(32)30-9-11-31(12-10-30)26-28-19-14-22(35-5)21(34-4)13-18(19)25(27)29-26/h6-8,13-14,16H,9-12,15H2,1-5H3,(H2,27,28,29)
iupac name: 1-[4-(4-amino-6,7-dimethoxyquinazolin-2-yl)piperazin-1-yl]-2-(2-methoxy-6-propan-2-ylphenoxy)ethanone
xref: CHEMBL430717
approved: f
ligand name: Rec 15/2615
type: SyntheticOrganicLigand

molidustat
canonical SMILES: O=c1n([nH]cc1n1ccnn1)c1ncnc(c1)N1CCOCC1
isomeric SMILES: O=c1n([nH]cc1n1ccnn1)c1ncnc(c1)N1CCOCC1
in ch i key: IJMBOKOTALXLKS-UHFFFAOYSA-N
in ch i: InChI=1S/C13H14N8O2/c22-13-10(20-2-1-16-18-20)8-17-21(13)12-7-11(14-9-15-12)19-3-5-23-6-4-19/h1-2,7-9,17H,3-6H2
comment: Molidustat is a compound which inhibits hypoxia inducible factor prolyl hydroxylase (HIF-PH) activity. HIF-PH inhibitors are being investigated as novel therapies for anemia, especially anemia caused by chronic kindney disease (CKD). It is hoped that HIF-PH inhibitors will provide a more effective alternative to the use of erythropoetin replacement therapy plus iron supplementation in CKD patients
iupac name: 2-(6-morpholin-4-ylpyrimidin-4-yl)-4-(triazol-1-yl)-1H-pyrazol-3-one
synonym: BAY 85-3934
synonym: BAY-853934
synonym: BAY85-3934
approved: f
ligand name: molidustat
type: SyntheticOrganicLigand

daidzein
canonical SMILES: Oc1ccc(cc1)c1coc2c(c1=O)ccc(c2)O
isomeric SMILES: Oc1ccc(cc1)c1coc2c(c1=O)ccc(c2)O
in ch i key: ZQSIJRDFPHDXIC-UHFFFAOYSA-N
in ch i: InChI=1S/C15H10O4/c16-10-3-1-9(2-4-10)13-8-19-14-7-11(17)5-6-12(14)15(13)18/h1-8,16-17H
comment: Daidzein is a soy phytoestrogen, which is metabolised to S-equol (PubChem CID 91469), an estrogen-like compound, in the presence of requisite gut flora. Daidzein may have beneficial health effects <Reference id=26529/>.
iupac name: 7-hydroxy-3-(4-hydroxyphenyl)chromen-4-one
xref: CHEMBL8145
synonym: 7,4'-dihydroxyisoflavone
approved: f
ligand name: daidzein
type: SyntheticOrganicLigand

daprodustat
in ch i key: RUEYEZADQJCKGV-UHFFFAOYSA-N
in ch i: InChI=1S/C19H27N3O6/c23-14(24)11-20-16(25)15-17(26)21(12-7-3-1-4-8-12)19(28)22(18(15)27)13-9-5-2-6-10-13/h12-13,15H,1-11H2,(H,20,25)(H,23,24)
comment: Daprodustat is a compound which inhibits hypoxia inducible factor prolyl hydroxylase (HIF-PH) activity. HIF-PH inhibitors are being investigated as novel therapies for anemia, especially anemia caused by chronic kindney disease (CKD). It is hoped that HIF-PH inhibitors will provide a more effective alternative to the use of erythropoetin replacement therapy plus iron supplementation in CKD patients
iupac name: 2-[(1,3-dicyclohexyl-2,4,6-trioxo-1,3-diazinane-5-carbonyl)amino]acetic acid
synonym: GSK-1278863
synonym: GSK1278863
synonym: GSK 1278863
synonym: Duvroq®
approved: t
ligand name: daprodustat
type: SyntheticOrganicLigand

roxadustat
in ch i key: YOZBGTLTNGAVFU-UHFFFAOYSA-N
in ch i: InChI=1S/C19H16N2O5/c1-11-15-9-13(26-12-5-3-2-4-6-12)7-8-14(15)18(24)17(21-11)19(25)20-10-16(22)23/h2-9,24H,10H2,1H3,(H,20,25)(H,22,23)
comment: Roxadustat is a compound which inhibits hypoxia inducible factor prolyl hydroxylase (HIF-PH) activity. HIF-PH inhibitors are being investigated as novel therapies for anemia, especially anemia caused by chronic kindney disease (CKD) <Reference id=28113/>. It is hoped that HIF-PH inhibitors will provide a more effective alternative to the use of erythropoetin replacement therapy plus iron supplementation in CKD patients.
iupac name: 2-[[4-hydroxy-1-methyl-7-(phenoxy)isoquinoline-3-carbonyl]amino]acetic acid
xref: CHEMBL2338329
synonym: FG-4592
synonym: FG4592
synonym: ASP-1517
synonym: ASP1517
synonym: Evrenzo®
approved: t
ligand name: roxadustat
type: SyntheticOrganicLigand

ixazomib
in ch i key: MXAYKZJJDUDWDS-LBPRGKRZSA-N
comment: Ixazomib is the first approved oral proteasome inhibitor. Ixazomib reversibly inhibits 20S proteasome activity. Like <Ligand id=6391/>, ixazomib primarily inhibits the chymotrypsin-like (β5) proteolytic site within the 20S proteasome, but its pharmacokinetics, pharmacodynamics, and antitumor activity are superior to those of bortezomib <Reference id=28084/>.
iupac name: [(1R)-1-[[2-[(2,5-dichlorobenzoyl)amino]acetyl]amino]-3-methylbutyl]boronic acid
xref: CHEMBL2141296
synonym: MLN2238
synonym: MLN-2238
synonym: MLN 2238
synonym: Ninlaro®
approved: t
ligand name: ixazomib
type: SyntheticOrganicLigand

WRC-0571
canonical SMILES: OC1CC2CC1CC2Nc1ncnc2c1nc(n2C)N(C(C)C)C
in ch i key: FTVZUYADPTUEKI-AYNROABZSA-N
in ch i: InChI=1S/C17H26N6O/c1-9(2)22(3)17-21-14-15(18-8-19-16(14)23(17)4)20-12-6-11-5-10(12)7-13(11)24/h8-13,24H,5-7H2,1-4H3,(H,18,19,20)/t10?,11?,12-,13?/m1/s1
comment: This ligand is represented in PubChem by CID 9902054 which does not include specification of chirality.
iupac name: 5-[[9-methyl-8-[methyl(propan-2-yl)amino]purin-6-yl]amino]bicyclo[2.2.1]heptan-2-ol
approved: f
ligand name: WRC-0571
type: SyntheticOrganicLigand

tenapanor
in ch i key: DNHPDWGIXIMXSA-CXNSMIOJSA-N
comment: Tenapanor is an inhibitor of the sodium/hydrogen exchanger 3 (NHE3, gene symbol SLC9A3) <Reference id=28076/>. Tenapanor is Compound 236 in patent US8541448 <Reference id=28078/>.
xref: CHEMBL3304485
synonym: AZD-1722
synonym: RDX-5791
synonym: AZD1722
synonym: Ibsrela®
approved: t
ligand name: tenapanor
type: SyntheticOrganicLigand

sparsentan
in ch i key: WRFHGDPIDHPWIQ-UHFFFAOYSA-N
in ch i: InChI=1S/C32H40N4O5S/c1-5-7-14-29-33-32(17-10-11-18-32)31(37)36(29)20-24-15-16-26(25(19-24)21-40-6-2)27-12-8-9-13-28(27)42(38,39)35-30-22(3)23(4)41-34-30/h8-9,12-13,15-16,19H,5-7,10-11,14,17-18,20-21H2,1-4H3,(H,34,35)
comment: Sparsentan (RE-021) is a selective dual-acting receptor antagonist with affinity for endothelin (A type) and angiotensin II receptors (Type 1) <Reference id=28074/><Reference id=28072/>. Sparsentan combines the active moieties of the selective AT1 receptor antagonist <Ligand id=589/> and a selective ETA receptor antagonist (see ligand 91 in <Reference id=28072/>).
iupac name: 2-[4-[(2-butyl-4-oxo-1,3-diazaspiro[4.4]non-1-en-3-yl)methyl]-2-(ethoxymethyl)phenyl]-N-(4,5-dimethyl-1,2-oxazol-3-yl)benzenesulfonamide
xref: CHEMBL539423
synonym: RE-021
synonym: compound 7 [PMID 15634011]
synonym: retrophin
synonym: DARA-a (Dual Acting Receptor Antagonist of angiotension and endothelin receptors)
synonym: BMS 346567
synonym: BMS-346567
synonym: BMS346567
approved: f
ligand name: sparsentan
type: SyntheticOrganicLigand

2-Cl-ADP(α-BH3)
canonical SMILES: OC1C(COP(=O)(OP(=O)(O)O)[B-])OC(C1O)n1cnc2c1nc(Cl)nc2N
in ch i key: XLTJNJOUVKOQCW-MWZJDIDNSA-N
iupac name: [[(2R,3S,4R,5R)-5-(6-amino-2-chloropurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-phosphonooxyphosphoryl]boron(1-)
approved: f
ligand name: 2-Cl-ADP(α-BH3)
type: SyntheticOrganicLigand

beloranib
in ch i key: ZEZFKUBILQRZCK-MJSCXXSSSA-N
in ch i: InChI=1S/C29H41NO6/c1-20(2)7-13-24-28(3,36-24)27-26(32-6)23(15-16-29(27)19-34-29)35-25(31)14-10-21-8-11-22(12-9-21)33-18-17-30(4)5/h7-12,14,23-24,26-27H,13,15-19H2,1-6H3/b14-10+/t23-,24-,26-,27-,28+,29+/m1/s1
comment: Beloranib is an investigational drug candidate for the treatment of obesity. The compound is a synthetic derivative of the antimicrobial agent fumagillin, from Aspergillus fumigatus. Beloranib is administered by subcutaneous injection.
iupac name: [(3R,4S,5S,6R)-5-methoxy-4-[(2R,3R)-2-methyl-3-(3-methylbut-2-enyl)oxiran-2-yl]-1-oxaspiro[2.5]octan-6-yl] (E)-3-[4-(2-dimethylaminoethoxy)phenyl]prop-2-enoate
synonym: ZGN-440
synonym: ZGN 440
synonym: CKD-732
synonym: O-(4-(2-Dimethylaminoethoxy)-trans-cinnamoyl)fumagillol
approved: f
ligand name: beloranib
type: SyntheticOrganicLigand

ISA-2011B
in ch i key: FSEZESVJDPKRDS-UWJYYQICSA-N
in ch i: InChI=1S/C22H18ClN3O4/c1-25-9-20(27)26-17(22(25)28)4-11-5-18-19(30-10-29-18)7-13(11)21(26)15-8-24-16-3-2-12(23)6-14(15)16/h2-3,5-8,17,21,24H,4,9-10H2,1H3/t17-,21-/m0/s1
comment: Patent search with this structure reveals SCHEMBL10020974 ID matching a structure (Analogue 1) in patent WO2010149944 <Reference id=28044/>. ISA-2011B is being evaluated pre-clinically as a potential anti-prostate cancer therapeutic <Reference id=28047/>.
approved: f
ligand name: ISA-2011B
type: SyntheticOrganicLigand

SKF-83959
canonical SMILES: CN1CCc2c(C(C1)c1cccc(c1)C)cc(c(c2Cl)O)O
isomeric SMILES: CN1CCc2c(C(C1)c1cccc(c1)C)cc(c(c2Cl)O)O
in ch i key: JXMYTVOBSFOHAF-UHFFFAOYSA-N
in ch i: InChI=1S/C18H20ClNO2/c1-11-4-3-5-12(8-11)15-10-20(2)7-6-13-14(15)9-16(21)18(22)17(13)19/h3-5,8-9,15,21-22H,6-7,10H2,1-2H3
comment: Some substituted benzazepines such as SKF-83959 are G-protein biased agonists of the dopamine D1 receptor and fail to activate arrestin recruitment <Reference id=28036/>.
iupac name: 6-chloro-3-methyl-1-(3-methylphenyl)-1,2,4,5-tetrahydro-3-benzazepine-7,8-diol
xref: CHEMBL574558
synonym: SKF83959
synonym: SKF 83959
approved: f
ligand name: SKF-83959
type: SyntheticOrganicLigand

remimazolam
in ch i key: GHUYIIGPWBMOGY-KRWDZBQOSA-N
in ch i: InChI=1S/C21H19BrN4O2/c1-13-12-26-18-8-6-14(22)11-15(18)20(16-5-3-4-10-23-16)25-17(21(26)24-13)7-9-19(27)28-2/h3-6,8,10-12,17H,7,9H2,1-2H3/t17-/m0/s1
comment: Remimazolam is a benzodiazepine type compound, that was developed as an ultra-short-acting sedative/anesthetic <Reference id=28033/><Reference id=41912/>. This compound combines the actions of the opioid analgesic <Ligand id=7292/> with that of the currently used sedative <Ligand id=3342/> (GABAA receptor modulator). Remimazolam is proposed as a safer alternative to the current standard of care.
iupac name: methyl 3-[(4S)-8-bromo-2-methyl-6-pyridin-2-yl-4H-imidazo[1,2-a][1,4]benzodiazepin-4-yl]propanoate
synonym: CNS-7056
synonym: Byfavo®
synonym: CNS7056
approved: t
ligand name: remimazolam
type: SyntheticOrganicLigand

A-381393
in ch i key: SAQMCVDGOIRQTC-UHFFFAOYSA-N
in ch i: InChI=1S/C20H24N4/c1-15-7-8-17(13-16(15)2)24-11-9-23(10-12-24)14-20-21-18-5-3-4-6-19(18)22-20/h3-8,13H,9-12,14H2,1-2H3,(H,21,22)
comment: A-381393 is reported as a potent and selective antagonist of the dopamine D4 receptor <Reference id=28009/>.
iupac name: 2-[[4-(3,4-dimethylphenyl)piperazin-1-yl]methyl]-1H-benzimidazole
xref: CHEMBL127257
synonym: A-381,393
synonym: A 381393
approved: f
ligand name: A-381393
type: SyntheticOrganicLigand

ML398
canonical SMILES: Clc1ccc(cc1)CN1CCOC(C1)CCc1ccccc1
isomeric SMILES: Clc1ccc(cc1)CN1CCO[C@@H](C1)CCc1ccccc1
in ch i key: CVKXGRRJHJHUFY-LJQANCHMSA-N
in ch i: InChI=1S/C19H22ClNO/c20-18-9-6-17(7-10-18)14-21-12-13-22-19(15-21)11-8-16-4-2-1-3-5-16/h1-7,9-10,19H,8,11-15H2/t19-/m1/s1
comment: ML398 is reported as a potent and selective antagonist of the dopamine D4 receptor <Reference id=28003/>.
iupac name: (2R)-4-[(4-chlorophenyl)methyl]-2-(2-phenylethyl)morpholine
approved: f
ligand name: ML398
type: SyntheticOrganicLigand

ABT-670
canonical SMILES: Cc1cccc(c1)C(=O)NCN1CCC(CC1)c1cccc[n+]1[O-]
isomeric SMILES: Cc1cccc(c1)C(=O)NCN1CCC(CC1)c1cccc[n+]1[O-]
in ch i key: PUMMPCXNEPHBNN-UHFFFAOYSA-N
in ch i: InChI=1S/C19H23N3O2/c1-15-5-4-6-17(13-15)19(23)20-14-21-11-8-16(9-12-21)18-7-2-3-10-22(18)24/h2-7,10,13,16H,8-9,11-12,14H2,1H3,(H,20,23)
comment: ABT-670 is an orally bioavailable agonist of the dopamine D4 receptor <Reference id=28002/>. The compound was designed as a potential treatment for erectile dysfunction.
iupac name: 3-methyl-N-[[4-(1-oxidopyridin-1-ium-2-yl)piperidin-1-yl]methyl]benzamide
xref: CHEMBL219182
synonym: ABT670
synonym: ABT 670
synonym: compound 6b [PMID 17149874]
approved: f
ligand name: ABT-670
type: SyntheticOrganicLigand

BED
canonical SMILES: CCCCNC(=O)c1cc(N)ccc1Oc1ccc(cc1)OCC
isomeric SMILES: CCCCNC(=O)c1cc(N)ccc1Oc1ccc(cc1)OCC
in ch i key: RDHPPQMUBJSJFR-UHFFFAOYSA-N
in ch i: InChI=1S/C19H24N2O3/c1-3-5-12-21-19(22)17-13-14(20)6-11-18(17)24-16-9-7-15(8-10-16)23-4-2/h6-11,13H,3-5,12,20H2,1-2H3,(H,21,22)
iupac name: 5-amino-N-butyl-2-(4-ethoxyphenoxy)benzamide
approved: f
ligand name: BED
type: SyntheticOrganicLigand

compound 101 [PMID: 21596927]
in ch i key: WFOVEDJTASPCIR-UHFFFAOYSA-N
in ch i: InChI=1S/C24H21F3N6O/c1-33-21(31-32-22(33)16-9-11-28-12-10-16)15-29-19-7-4-6-17(13-19)23(34)30-14-18-5-2-3-8-20(18)24(25,26)27/h2-13,29H,14-15H2,1H3,(H,30,34)
comment: Compound 101 is an inhibitor of the beta adrenergic receptor kinase 1 (aka GRK2, gene symbol ADRBK1) and beta adrenergic receptor kinase 2 (aka GRK3, gene symbol ADRBK2) <Reference id=27971/>. Compound 101 is one of the chemical structures covered by patent WO2007034846 A1 <Reference id=27970/>.
synonym: cmpd101
synonym: Takeda compound 101
approved: f
ligand name: compound 101 [PMID: 21596927]
type: SyntheticOrganicLigand

LP-211
in ch i key: BQEDZLDNNBDKDS-UHFFFAOYSA-N
in ch i: InChI=1S/C30H34N4O/c31-23-25-14-16-26(17-15-25)24-32-30(35)13-5-2-8-18-33-19-21-34(22-20-33)29-12-7-6-11-28(29)27-9-3-1-4-10-27/h1,3-4,6-7,9-12,14-17H,2,5,8,13,18-22,24H2,(H,32,35)
comment: LP-211 is reported to be a selective agonist of the serotonin 5-HT7 receptor <Reference id=27969/>.
iupac name: N-[(4-cyanophenyl)methyl]-6-[4-(2-phenylphenyl)piperazin-1-yl]hexanamide
xref: CHEMBL522691
synonym: compound 25 [PMID 18800769]
approved: f
ligand name: LP-211
type: SyntheticOrganicLigand

LP-44
in ch i key: JNBBJUHCODFLEG-UHFFFAOYSA-N
in ch i: InChI=1S/C27H37N3OS/c1-32-26-15-7-6-14-25(26)30-20-18-29(19-21-30)17-8-2-3-16-27(31)28-24-13-9-11-22-10-4-5-12-23(22)24/h4-7,10,12,14-15,24H,2-3,8-9,11,13,16-21H2,1H3,(H,28,31)
comment: LP-44 is a selective serotonin 5-HT7 receptor agonist <Reference id=27968/>.
iupac name: 6-[4-(2-methylsulfanylphenyl)piperazin-1-yl]-N-(1,2,3,4-tetrahydronaphthalen-1-yl)hexanamide
xref: CHEMBL225284
synonym: compound 5 [PMID 17649988]
approved: f
ligand name: LP-44
type: SyntheticOrganicLigand

ethacrynic acid
canonical SMILES: CCC(=C)C(=O)c1ccc(c(c1Cl)Cl)OCC(=O)O
isomeric SMILES: CCC(=C)C(=O)c1ccc(c(c1Cl)Cl)OCC(=O)O
in ch i key: AVOLMBLBETYQHX-UHFFFAOYSA-N
in ch i: InChI=1S/C13H12Cl2O4/c1-3-7(2)13(18)8-4-5-9(12(15)11(8)14)19-6-10(16)17/h4-5H,2-3,6H2,1H3,(H,16,17)
comment: Ethacrynic acid is a loop diuretic.
iupac name: 2-[2,3-dichloro-4-(2-methylidenebutanoyl)phenoxy]acetic acid
xref: CHEMBL456
synonym: Edecrin®
synonym: MK-595
approved: t
ligand name: ethacrynic acid
type: SyntheticOrganicLigand

LP-12
in ch i key: NMZIDFFHGCRAJV-UHFFFAOYSA-N
in ch i: InChI=1S/C32H39N3O/c36-32(33-30-18-11-15-26-14-6-7-16-28(26)30)20-5-2-10-21-34-22-24-35(25-23-34)31-19-9-8-17-29(31)27-12-3-1-4-13-27/h1,3-4,6-9,12-14,16-17,19,30H,2,5,10-11,15,18,20-25H2,(H,33,36)
comment: LP-12 is a selective serotonin 5-HT7 receptor agonist <Reference id=27968/>.
iupac name: 6-[4-(2-phenylphenyl)piperazin-1-yl]-N-(1,2,3,4-tetrahydronaphthalen-1-yl)hexanamide
xref: CHEMBL243954
synonym: compound 21 [PMID 17649988]
approved: f
ligand name: LP-12
type: SyntheticOrganicLigand

AS-19
canonical SMILES: CN(C1CCc2c(C1)cccc2c1c(C)nn(c1C)C)C
isomeric SMILES: CN([C@H]1CCc2c(C1)cccc2c1c(C)nn(c1C)C)C
in ch i key: BTTOYOKCLDAHHO-HNNXBMFYSA-N
in ch i: InChI=1S/C18H25N3/c1-12-18(13(2)21(5)19-12)17-8-6-7-14-11-15(20(3)4)9-10-16(14)17/h6-8,15H,9-11H2,1-5H3/t15-/m0/s1
comment: AS-19 is a selective serotonin 5-HT7 receptor agonist <Reference id=27966/>. 5-HT7 receptor agonists may be usful tools in the investigation of the receptor's function in memory <Reference id=27967/> and pain <Reference id=14821/>.
iupac name: (2S)-N,N-dimethyl-5-(1,3,5-trimethylpyrazol-4-yl)-1,2,3,4-tetrahydronaphthalen-2-amine
xref: CHEMBL2164327
synonym: AS 19
synonym: AS19
approved: f
ligand name: AS-19
type: SyntheticOrganicLigand

JNJ-18038683
canonical SMILES: Clc1ccc(cc1)c1nn(c2c1CCNCC2)Cc1ccccc1
isomeric SMILES: Clc1ccc(cc1)c1nn(c2c1CCNCC2)Cc1ccccc1
in ch i key: UKJPMZGILXATGT-UHFFFAOYSA-N
in ch i: InChI=1S/C20H20ClN3/c21-17-8-6-16(7-9-17)20-18-10-12-22-13-11-19(18)24(23-20)14-15-4-2-1-3-5-15/h1-9,22H,10-14H2
comment: JNJ-18038683 is a 1:1 mixture of PubChem CID 11151899 and citric acid (2-hydroxypropane-1,2,3-tricarboxylic acid, PubChem CID 311) <Reference id=27965/>. We only show the structure for the former moeity which is a selective serotonin 5-HT7 receptor antagonist.
iupac name: 3-(4-chlorophenyl)-1-(phenylmethyl)-5,6,7,8-tetrahydro-4H-pyrazolo[5,4-d]azepine
synonym: JNJ 18038683
approved: f
ligand name: JNJ-18038683
type: SyntheticOrganicLigand

DR-4004
in ch i key: JBQOYPLKTTXLSQ-UHFFFAOYSA-N
in ch i: InChI=1S/C26H30N2O/c29-25-26(16-7-11-22-10-6-12-23(27-25)24(22)26)15-4-5-17-28-18-13-21(14-19-28)20-8-2-1-3-9-20/h1-3,6,8-10,12-13H,4-5,7,11,14-19H2,(H,27,29)
comment: DR-4004 is a selective antagonist of the serotonin 5-HT7 receptor <Reference id=27963/>.
iupac name: 2a-[4-(4-phenyl-3,6-dihydro-2H-pyridin-1-yl)butyl]-1,3,4,5-tetrahydrobenzo[cd]indol-2-one
xref: CHEMBL69257
synonym: compound 7 [PMID 10052959]
approved: f
ligand name: DR-4004
type: SyntheticOrganicLigand

[11C]GSK215083
in ch i key: PXVJEDOZGDZJQY-BJUDXGSMSA-N
in ch i: InChI=1S/C20H20FN3O2S/c1-23-8-10-24(11-9-23)19-7-2-4-15-12-18(14-22-20(15)19)27(25,26)17-6-3-5-16(21)13-17/h2-7,12-14H,8-11H2,1H3/i1-1
comment: [11C]GSK215083 is used as a PET radioligand, to allow in vivo imaging of serotonin 5-HT6 receptor distribution <Reference id=27961/>. GSK215083 is a 5-HT6 receptor antagonist with a lipophilicity profile permitting brain penetrance <Reference id=27962/>.
iupac name: 3-(3-fluorophenyl)sulfonyl-8-(4-methylpiperazin-1-yl)quinoline
approved: f
ligand name: [11C]GSK215083
type: SyntheticOrganicLigand

WAY-208466
in ch i key: SFSFIDVAEMDPIP-UHFFFAOYSA-N
in ch i: InChI=1S/C17H18FN3O2S/c1-20(2)9-10-21-12-16(15-7-4-8-19-17(15)21)24(22,23)14-6-3-5-13(18)11-14/h3-8,11-12H,9-10H2,1-2H3
comment: WAY-208466 is a selective serotonin 5-HT6 receptor agonist <Reference id=13492/><Reference id=27960/>.
iupac name: 2-[3-(3-fluorophenyl)sulfonylpyrrolo[2,3-b]pyridin-1-yl]-N,N-dimethylethanamine
xref: CHEMBL571858
approved: f
ligand name: WAY-208466
type: SyntheticOrganicLigand

relenopride
in ch i key: KGMMSPVVHZGPHL-NRFANRHFSA-N
comment: Relenopride (YKP10811) is a partial agonist which is selective for the serotonin 5-HT4 receptor <Reference id=27958/>.
iupac name: [(1S)-3-[4-[[(4-amino-5-chloro-2-methoxybenzoyl)amino]methyl]piperidin-1-yl]-1-(4-fluorophenyl)propyl] carbamate
synonym: YKP10811
approved: f
ligand name: relenopride
type: SyntheticOrganicLigand

TD-8954
in ch i key: MZOITCJKGUIQEI-UHFFFAOYSA-N
in ch i: InChI=1S/C25H37N5O3/c1-17(2)23-27-21-6-4-5-20(22(21)28-23)24(31)26-15-18-7-11-29(12-8-18)16-19-9-13-30(14-10-19)25(32)33-3/h4-6,17-19H,7-16H2,1-3H3,(H,26,31)(H,27,28)
comment: TD-8954 is a potent and selective agonist of the 5-HT4 receptor <Reference id=27956/><Reference id=27957/>. The compound is being investigated for its gastrointestinal prokinetic action.
iupac name: methyl 4-[[4-[[(2-propan-2-yl1H-benzimidazole-4-carbonyl)amino]methyl]piperidin-1-yl]methyl]piperidine-1-carboxylate
xref: CHEMBL2402904
synonym: compound 18 [PMID 23756062]
approved: f
ligand name: TD-8954
type: SyntheticOrganicLigand

velusetrag
in ch i key: HXLOHDZQBKCUCR-VTHDOGFWSA-N
in ch i: InChI=1S/C25H36N4O5S/c1-16(2)29-23-8-6-5-7-17(23)11-22(25(29)32)24(31)26-18-12-19-9-10-20(13-18)28(19)15-21(30)14-27(3)35(4,33)34/h5-8,11,16,18-21,30H,9-10,12-15H2,1-4H3,(H,26,31)/t18?,19-,20+,21-/m0/s1
comment: Velusetrag is a potent and selective, orally available agonist of the 5-HT4 receptor. The compound is being investigated as a treatment for chronic constipation <Reference id=27948/><Reference id=27947/> and irritable bowel syndrome <Reference id=27949/>.
iupac name: N-[(1R,5S)-8-[(2R)-2-hydroxy-3-(methyl-methylsulfonylamino)propyl]-8-azabicyclo[3.2.1]octan-3-yl]-2-oxo-1-propan-2-ylquinoline-3-carboxamide
xref: CHEMBL2087337
synonym: TD-5108
synonym: compound 15 [PMID 22959244]
approved: f
ligand name: velusetrag
type: SyntheticOrganicLigand

BF-1
in ch i key: ANZVBVKYXOGOQC-UHFFFAOYSA-N
in ch i: InChI=1S/C22H25NO2S/c1-4-25-16-8-9-17-20(14-16)26-19-7-5-6-18(24-3)22(19)21(17)15-10-12-23(2)13-11-15/h5-9,14H,4,10-13H2,1-3H3
comment: BF-1 is a selective antagonist of the 5-HT2B receptor, being investigated preclinically as an anti-migraine therapeutic <Reference id=27946/>. Because this compound lacks high affinities for other monoamine receptors it should have fewer monoanimergic side effects than reported for previously used and withdrawn 5-HT2B antagonists such as <Ligand id=134/> and <Ligand id=93/>. BF-1 is the result of structural modification of the chemical scaffold of <Ligand id=7232/>, a compound with high affinity for 5-HT2A, 2B, 2C, histamine H1, adrenaline α1A and muscarinic M2 receptors <Reference id=27946/>.
iupac name: 4-(6-ethoxy-1-methoxythioxanthen-9-ylidene)-1-methylpiperidine
approved: f
ligand name: BF-1
type: SyntheticOrganicLigand

pimavanserin
in ch i key: RKEWSXXUOLRFBX-UHFFFAOYSA-N
in ch i: InChI=1S/C25H34FN3O2/c1-19(2)18-31-24-10-6-20(7-11-24)16-27-25(30)29(23-12-14-28(3)15-13-23)17-21-4-8-22(26)9-5-21/h4-11,19,23H,12-18H2,1-3H3,(H,27,30)
comment: Pimavanserin is an inverse agonist of the serotonin 5-HT2A receptor <Reference id=27944/>. Pharmaceutical formulations contain pimavanserin tartrate (PubChem CID 67017013) .
iupac name: 1-[(4-fluorophenyl)methyl]-1-(1-methylpiperidin-4-yl)-3-[[4-(2-methylpropoxy)phenyl]methyl]urea
xref: CHEMBL2111101
synonym: ACP 103
synonym: Nuplazid (proposed trade name)
synonym: ACP-103
synonym: ACP103
approved: t
ligand name: pimavanserin
type: SyntheticOrganicLigand

5-BODMT
canonical SMILES: CCCC(=O)Cc1ccc2c(c1)c(CCN(C)C)c[nH]2
isomeric SMILES: CCCC(=O)Cc1ccc2c(c1)c(CCN(C)C)c[nH]2
in ch i key: OQDBJMBOPCUBGS-UHFFFAOYSA-N
in ch i: InChI=1S/C17H24N2O/c1-4-5-15(20)10-13-6-7-17-16(11-13)14(12-18-17)8-9-19(2)3/h6-7,11-12,18H,4-5,8-10H2,1-3H3
comment: 5-BODMT is a novel compound with >60-fold selectivity for the 5-HT1F receptor compared to the 5-HT1E receptor <Reference id=27942/>.
iupac name: 1-{3-[2-(dimethylamino)ethyl]-1H-indol-5-yl}pentan-2-one
synonym: 5-N-butyryloxy-N,N-dimethyltryptamine
synonym: compound 10 [PMID 21422162]
approved: f
ligand name: 5-BODMT
type: SyntheticOrganicLigand

MRS5698
canonical SMILES: CNC(=O)C12CC1C(C(C2O)O)n1cnc2c1nc(C#Cc1ccc(c(c1)F)F)nc2NCc1cccc(c1)Cl
in ch i key: LYLLLJJYBWLGHW-CIZVZKTGSA-N
iupac name: (1S,2R,3S,4R,5S)-4-(6-{[(3-chlorophenyl)methyl]amino}-2-[2-(3,4-difluorophenyl)ethynyl]-9H-purin-9-yl)-2,3-dihydroxy-N-methylbicyclo[3.1.0]hexane-1-carboxamide
xref: CHEMBL2064657
synonym: MRS-5698
synonym: MRS 5698
approved: f
ligand name: MRS5698
type: SyntheticOrganicLigand

UK-432,097
in ch i key: ZOTHAEBAWXWVID-HXEFRTELSA-N
in ch i: InChI=1S/C40H47N11O6/c1-2-41-37(54)33-31(52)32(53)39(57-33)51-24-46-30-34(45-23-28(25-11-5-3-6-12-25)26-13-7-4-8-14-26)48-35(49-36(30)51)38(55)43-19-20-44-40(56)47-27-16-21-50(22-17-27)29-15-9-10-18-42-29/h3-15,18,24,27-28,31-33,39,52-53H,2,16-17,19-23H2,1H3,(H,41,54)(H,43,55)(H2,44,47,56)(H,45,48,49)/t31-,32+,33-,39+/m0/s1
comment: Selective agonist of the adenosine A2A receptor
iupac name: 6-[2,2-di(phenyl)ethylamino]-9-[(2R,3R,4S,5S)-5-(ethylcarbamoyl)-3,4-dihydroxyoxolan-2-yl]-N-[2-[(1-pyridin-2-ylpiperidin-4-yl)carbamoylamino]ethyl]purine-2-carboxamide
xref: CHEMBL1096896
synonym: UK432,097
synonym: UK432097
approved: f
ligand name: UK-432,097
type: SyntheticOrganicLigand

compound A [PMID 24997608]
in ch i key: WUJVPELCYCESAP-UHFFFAOYSA-N
comment: Compound A is a selective agonist of the free fatty acid receptor 4 (FFA4R) <Reference id=27924/>. The compound is a small molecule, orally active mimic of ω-3-fatty acids, the endogenous ligands of FFA4R <Reference id=12858/>.
iupac name: 2-[3-[2-chloro-5-(trifluoromethoxy)phenyl]-3-azaspiro[5.5]undecan-9-yl]acetic acid
approved: f
ligand name: compound A [PMID 24997608]
type: SyntheticOrganicLigand

GLPG0974
in ch i key: MPMKMQHJHDHPBE-RUZDIDTESA-N
comment: GLPG0974 is a lead clinical development candidate compound which acts as an antagonist of the free fatty acid receptor 2 (FFA2) <Reference id=27921/>. FFA2 is a GPCR involved in the mediation of inflammatory responses.
iupac name: 4-[[(2R)-1-(1-benzothiophene-3-carbonyl)-2-methylazetidine-2-carbonyl]-[(3-chlorophenyl)methyl]amino]butanoic acid
synonym: compound 99 [PMID 25380412]
approved: f
ligand name: GLPG0974
type: SyntheticOrganicLigand

eleclazine
in ch i key: YNUAEEJQYHYLMS-UHFFFAOYSA-N
in ch i: InChI=1S/C21H16F3N3O3/c22-21(23,24)30-16-5-2-14(3-6-16)15-4-7-18-17(12-15)20(28)27(10-11-29-18)13-19-25-8-1-9-26-19/h1-9,12H,10-11,13H2
comment: Eleclazine is a sodium channel inhibitor, modulating cardiac late Na+ currents via the Nav1.5 (gene symbol SCN5A) channel. The compound is a dihydrobenzodiazepine type structure. Dihydrobenzodiazepine scaffolds are being developed as α-helix mimetics, with the potential to inhibit protein-protein interactions <Reference id=27891/><Reference id=27890/><Reference id=27889/><Reference id=27892/>. This chemical structure and its use is covered by patent US20150038489 <Reference id=27893/>.
iupac name: 4-(pyrimidin-2-ylmethyl)-7-[4-(trifluoromethoxy)phenyl]-2,3-dihydro-1,4-benzoxazepin-5-one
synonym: GS-6615
synonym: GS6615
synonym: GS 6615
approved: f
ligand name: eleclazine
type: SyntheticOrganicLigand

I-BRD9
in ch i key: WRUWGLUCNBMGPS-UHFFFAOYSA-N
comment: This structure was drawn from the Structural Genomics Consortium's chemical probe page for I-BRD9 <Reference id=27838/>. I-BRD9 is the first selective tool compound which will be useful in resolving the biological function of bromodomain containing 9 (BRD9) <Reference id=27839/>. This is a compound from the Structural Genomics Consortium's (SGC) Epigenetics Probes Collection.
iupac name: N-(1,1-dioxo-1λ6-thian-4-yl)-5-ethyl-4-oxo-7-[3-(trifluoromethyl)phenyl]-4H,5H-thieno[3,2-c]pyridine-2-carboximidamide
synonym: GSK602
synonym: compound 45 [PMID 25856009]
approved: f
ligand name: I-BRD9
type: SyntheticOrganicLigand

compound 34 [PMID: 25974391]
in ch i key: KNVIUMWNYXDULF-UHFFFAOYSA-N
in ch i: InChI=1S/C24H25N3O7S/c1-26-19-13-18(25-35(29,30)17-10-11-21(32-4)23(12-17)33-5)22(14-20(19)27(2)24(26)28)34-16-8-6-15(31-3)7-9-16/h6-14,25H,1-5H3
comment: Compound 34 is reported as tool compound which acts as an inhibitor of the enzyme tripartite motif containing 24 (TRIM24) and of the bromodomain protein, bromodomain and PHD finger containing, 1 (BRPF1) <Reference id=27837/>.
iupac name: 3,4-dimethoxy-N-[6-(4-methoxyphenoxy)-1,3-dimethyl-2-oxo-2,3-dihydro-1H-1,3-benzodiazol-5-yl]benzene-1-sulfonamide
approved: f
ligand name: compound 34 [PMID: 25974391]
type: SyntheticOrganicLigand

DS-437
in ch i key: CACMCLIHCDTJHL-XLAISSFRSA-N
in ch i: InChI=1S/C15H23N7O4S/c1-2-17-15(25)18-3-4-27-5-8-10(23)11(24)14(26-8)22-7-21-9-12(16)19-6-20-13(9)22/h6-8,10-11,14,23-24H,2-5H2,1H3,(H2,16,19,20)(H2,17,18,25)/t8-,10+,11-,14?/m1/s1
comment: DS-437 is reported as a dual inhibitor of the protein arginine methyltransferases PRMT7 and PRMT5 <Reference id=27832/>.
iupac name: 1-[2-[[(2S,3R,4R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methylsulfanyl]ethyl]-3-ethylurea
synonym: DS437
approved: f
ligand name: DS-437
type: SyntheticOrganicLigand

gastrin-14
in ch i key: SSBRJDBGIVUNDK-QOGDCIHTSA-N
comment: Sulfated form of gastrin-14.
approved: f
ligand name: gastrin-14
type: PeptideLigand

desulfated gastrin-34
in ch i key: DKONFPYEAKZHHO-JCVYGFDXSA-N
approved: f
ligand name: desulfated gastrin-34
type: PeptideLigand

desulfated gastrin-17
in ch i key: GKDWRERMBNGKCZ-RNXBIMIWSA-N
synonym: little gastrin I
approved: f
ligand name: desulfated gastrin-17
type: PeptideLigand

retosiban
in ch i key: PLVGDGRBPMVYPB-FDUHJNRSSA-N
in ch i: InChI=1S/C27H34N4O5/c1-4-16(2)23-25(32)29-22(20-13-18-7-5-6-8-19(18)14-20)26(33)31(23)24(21-15-36-17(3)28-21)27(34)30-9-11-35-12-10-30/h5-8,15-16,20,22-24H,4,9-14H2,1-3H3,(H,29,32)/t16-,22+,23+,24+/m0/s1
comment: Retosiban is a investigational non-peptide oxytocin antagonist <Reference id=27850/><Reference id=7334/>.
iupac name: (3R,6R)-6-[(2S)-butan-2-yl]-3-(2,3-dihydro-1H-inden-2-yl)-1-[(1R)-1-(2-methyl-1,3-oxazol-4-yl)-2-morpholin-4-yl-2-oxoethyl]piperazine-2,5-dione
xref: CHEMBL429736
synonym: GSK-221,149-A
synonym: GSK-221149A
synonym: GSK 221149A
synonym: GSK221149A
approved: f
ligand name: retosiban
type: SyntheticOrganicLigand

omarigliptin
in ch i key: MKMPWKUAHLTIBJ-ISTRZQFTSA-N
comment: Omarigliptin is an investigational long-acting inhibitor of dipeptidyl peptidase 4 (DPP4) <Reference id=27849/>. The first DPP4 inhibitor to be clinically approved was <Ligand id=6286/>. This has subsequently been joined by several more drugs such as <Ligand id=6310/>, <Ligand id=6316/>, <Ligand id=6318/> and <Ligand id=6319/>.
iupac name: (2R,3S,5R)-2-(2,5-difluorophenyl)-5-(2-methylsulfonyl-4,6-dihydropyrrolo[3,4-c]pyrazol-5-yl)oxan-3-amine
xref: CHEMBL2105762
synonym: MK-3102
synonym: MK3102
synonym: MK 3102
approved: f
ligand name: omarigliptin
type: SyntheticOrganicLigand

α-methylphenylalanine
canonical SMILES: OC(=O)C(Cc1ccccc1)(N)C
isomeric SMILES: OC(=O)C(Cc1ccccc1)(N)C
in ch i key: HYOWVAAEQCNGLE-UHFFFAOYSA-N
in ch i: InChI=1S/C10H13NO2/c1-10(11,9(12)13)7-8-5-3-2-4-6-8/h2-6H,7,11H2,1H3,(H,12,13)
iupac name: 2-amino-2-methyl-3-phenylpropanoic acid
xref: CHEMBL1222268
approved: f
ligand name: α-methylphenylalanine
type: MetaboliteLigand

evacetrapib
in ch i key: IHIUGIVXARLYHP-UXNJHFGPSA-N
in ch i: InChI=1S/C31H36F6N6O2/c1-18-11-19(2)27-25(12-18)26(5-4-10-42(27)16-20-6-8-22(9-7-20)28(44)45)43(29-38-40-41(3)39-29)17-21-13-23(30(32,33)34)15-24(14-21)31(35,36)37/h11-15,20,22,26H,4-10,16-17H2,1-3H3,(H,44,45)/t20?,22?,26-/m0/s1
comment: Evacetrapib is a cholesterylester transfer protein (CETP) inhibitor <Reference id=27847/>. CETP was considered as a target for prevention of dyslipidemia and resucing cardiovascular mortality, with CETP inhibitors proposed as a direct route to raise HDL. Clinical trial results for a number of CETP inhibitors have failed to show clinical benefit. Failed candidates include evacetrapib, <Ligand id=8400/>, torcetrapib, and dalcetrapib <Reference id=42981/>.
iupac name: 4-[[(5S)-5-[[3,5-bis(trifluoromethyl)phenyl]methyl-(2-methyltetrazol-5-yl)amino]-7,9-dimethyl-2,3,4,5-tetrahydro-1-benzazepin-1-yl]methyl]cyclohexane-1-carboxylic acid
xref: CHEMBL2017179
synonym: LY-2484595
synonym: LY2484595
approved: f
ligand name: evacetrapib
type: SyntheticOrganicLigand

anacetrapib
in ch i key: MZZLGJHLQGUVPN-HAWMADMCSA-N
in ch i: InChI=1S/C30H25F10NO3/c1-14(2)22-11-23(25(43-4)12-24(22)31)21-6-5-18(28(32,33)34)9-17(21)13-41-15(3)26(44-27(41)42)16-7-19(29(35,36)37)10-20(8-16)30(38,39)40/h5-12,14-15,26H,13H2,1-4H3/t15-,26-/m0/s1
comment: Anacetrapib is a small molecule that inhibits cholesterylester transfer protein (CETP; P11597) <Reference id=27846/><Reference id=42980/>. CETP was considered as a target for prevention of dyslipidemia and resucing cardiovascular mortality, with CETP inhibitors proposed as a direct route to raise HDL. Clinical trial results for a number of CETP inhibitors have failed to show clinical benefit. Failed candidates include <Ligand id=8401/>, anacetrapib, torcetrapib, and dalcetrapib <Reference id=42981/>.
iupac name: (4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-3-[[2-(4-fluoro-2-methoxy-5-propan-2-ylphenyl)-5-(trifluoromethyl)phenyl]methyl]-4-methyl-1,3-oxazolidin-2-one
xref: CHEMBL1800807
synonym: MK 0859
synonym: MK0859
synonym: MK-0859
approved: f
ligand name: anacetrapib
type: SyntheticOrganicLigand

mithramycin
in ch i key: CFCUWKMKBJTWLW-BKHRDMLASA-N
comment: We show one representation of mithramycin here. As a natural product there are alternate chemical structures due to the complex stereochemistry. Also known as plicamycin, the compound has been used clinically as an antineoplastic antibacterial (produced by Streptomyces plicatus).
iupac name: (2S,3S)-2-[(2S,4R,5R,6R)-4-[(2S,4R,5S,6R)-4-[(2S,4S,5R,6R)-4,5-dihydroxy-4,6-dimethyloxan-2-yl]oxy-5-hydroxy-6-methyloxan-2-yl]oxy-5-hydroxy-6-methyloxan-2-yl]oxy-3-[(1S,3S,4R)-3,4-dihydroxy-1-methoxy-2-oxopentyl]-6-[(2S,4R,5R,6R)-4-[(2S,4R,5S,6R)-4,5-dihydroxy-6-methyloxan-2-yl]oxy-5-hydroxy-6-methyloxan-2-yl]oxy-8,9-dihydroxy-7-methyl-3,4-dihydro-2H-anthracen-1-one
synonym: Mithracin®
synonym: aureolic acid
synonym: mithramycin A
synonym: MMA
approved: t
ligand name: mithramycin
type: NaturalProductLigand

MB-3
canonical SMILES: CCCC1OC(=O)C(=O)C1C(=O)O
isomeric SMILES: CCC[C@@H]1OC(=O)C(=O)[C@H]1C(=O)O
in ch i key: AKWJFOMNTDKSRR-WHFBIAKZSA-N
in ch i: InChI=1S/C8H10O5/c1-2-3-4-5(7(10)11)6(9)8(12)13-4/h4-5H,2-3H2,1H3,(H,10,11)/t4-,5-/m0/s1
comment: MB-3 is reported as a cell-permeable small-molecule inhibitor of the histone acetyltransferase enzyme, general control nonderepressible 5 (GCN5, gene symbol KAT2B) <Reference id=27809/>. In vitro, MB-3 has been shown to inhibit GCN5-driven acetylation of the chimeric oncoprotein E2A-PBX1 <Reference id=27807/>. E2A-PBX1 is a non-histone target of GCN5 <Reference id=27808/>. A 2017 article by Dahlin et al. suggests that the thiol-reactivity of MB-3 brings in to question its activity as a selective HAT inhibitor <Reference id=33784/>.
iupac name: (2S,3S)-4,5-dioxo-2-propyloxolane-3-carboxylic acid
synonym: α-methylene-γ-butyrolactone 3
approved: f
ligand name: MB-3
type: SyntheticOrganicLigand

DZNep
canonical SMILES: OCC1CC(C(C1O)O)n1cnc2c1ccnc2N
isomeric SMILES: OCC1CC([C@@H]([C@@H]1O)O)n1cnc2c1ccnc2N
in ch i key: XNJHAZWZQGXOSC-FDNQDJDWSA-N
in ch i: InChI=1S/C12H16N4O3/c13-12-9-7(1-2-14-12)16(5-15-9)8-3-6(4-17)10(18)11(8)19/h1-2,5-6,8,10-11,17-19H,3-4H2,(H2,13,14)/t6?,8?,10-,11+/m1/s1
comment: DZNep was originally identified as an inhibitor of S-adenosylhomocysteine (AdoHcy) hydrolase <Reference id=27805/>. Subsequently DZNep has been reported to inhibit EZH2 histone methyltransferase activity <Reference id=27804/>.
iupac name: 3-{4-amino-1H-imidazo[4,5-c]pyridin-1-yl}-5-(hydroxymethyl)cyclopentane-1,2-diol
xref: CHEMBL154745
synonym: 3-deazaneplanocin A
approved: f
ligand name: DZNep
type: SyntheticOrganicLigand

CHR-3996
in ch i key: QRGHOAATPOLDPF-VQFNDLOPSA-N
in ch i: InChI=1S/C20H19FN6O2/c21-13-2-4-17-11(5-13)1-3-14(25-17)8-22-18-15-9-27(10-16(15)18)20-23-6-12(7-24-20)19(28)26-29/h1-7,15-16,18,22,29H,8-10H2,(H,26,28)/t15-,16+,18+
comment: The discovery of CHR-3996 is reported in <Reference id=27800/>. CHR-3996 is described as an orally active histone deacetylase (HDAC) inhibitor, with selectivity for Class I HDACs. PubChem CID 49857317 represents this molecule wih alternative stereochemistry.
iupac name: 2-[(1R,5S,6R)-6-{[(6-fluoroquinolin-2-yl)methyl]amino}-3-azabicyclo[3.1.0]hexan-3-yl]-N-hydroxypyrimidine-5-carboxamide
xref: CHEMBL1801250
synonym: compound 21r [PMID 21080647]
synonym: CHR3996
synonym: CHR 3996
approved: f
ligand name: CHR-3996
type: SyntheticOrganicLigand

ORY-1001
canonical SMILES: NC1CCC(CC1)NC1CC1c1ccccc1
isomeric SMILES: NC1CCC(CC1)N[C@@H]1C[C@H]1c1ccccc1
in ch i key: ALHBJBCQLJZYON-PFSRBDOWSA-N
in ch i: InChI=1S/C15H22N2/c16-12-6-8-13(9-7-12)17-15-10-14(15)11-4-2-1-3-5-11/h1-5,12-15,17H,6-10,16H2/t12?,13?,14-,15+/m0/s1
comment: ORY-1001 is a selective and irreversible inhibitor of lysine (K)-specific demethylase 1A (KDM1A, aka LSD1) <Reference id=32716/>, in clinical development by Oryzon Genomics. Structurally it is a derivative of <Ligand id=5281/>. ORY-1001 is claimed in patent WO2010084160 A1 <Reference id=27799/>. We provide the structure for the parent compound and the dichloride salt is represented in PubChem CID 71664305.
iupac name: 4-N-[(1R,2S)-2-phenylcyclopropyl]cyclohexane-1,4-diamine
synonym: RG-6016
approved: f
ligand name: ORY-1001
type: SyntheticOrganicLigand

UNC0321
in ch i key: AULLUGALUBVBDD-UHFFFAOYSA-N
in ch i: InChI=1S/C27H45N7O3/c1-31(2)15-16-36-17-18-37-25-20-23-22(19-24(25)35-5)26(28-21-7-11-33(4)12-8-21)30-27(29-23)34-10-6-9-32(3)13-14-34/h19-21H,6-18H2,1-5H3,(H,28,29,30)
comment: UNC0321 was the first reported picomolar inhibitor of the histone methyltransferase, G9a (eq. euchromatic histone-lysine N-methyltransferase 2, EHMT2) <Reference id=27794/>. G9a catalyses methylation of lysine 9 of histone H3 (H3K9) and lysine 373 (K373) of the tumour suppressor, p53 <Reference id=27797/>, and is reported to be overexpressed in human cancers.
iupac name: 7-[2-[2-(dimethylamino)ethoxy]ethoxy]-6-methoxy-2-(4-methyl-1,4-diazepan-1-yl)-N-(1-methylpiperidin-4-yl)quinazolin-4-amine
xref: CHEMBL1214066
synonym: UNC-0321
synonym: UNC 0321
approved: f
ligand name: UNC0321
type: SyntheticOrganicLigand

chaetocin
in ch i key: PZPPOCZWRGNKIR-UHFFFAOYSA-N
in ch i: InChI=1S/C30H28N6O6S4/c1-33-21(39)27-11-25(15-7-3-5-9-17(15)31-19(25)35(27)23(41)29(33,13-37)45-43-27)26-12-28-22(40)34(2)30(14-38,46-44-28)24(42)36(28)20(26)32-18-10-6-4-8-16(18)26/h3-10,19-20,31-32,37-38H,11-14H2,1-2H3
comment: Chaetocin is a fungal mycotoxin specifically inhibiting the histone methyltransferase (HMT), suppressor of variegation 3-9 homolog 1 (SUV39H1) <Reference id=27790/><Reference id=27793/>. SUV39H1 is the main enzyme responsible for the trimethylation of lysine 9 in histone H3. We show the chemical structure here without any stereochemical specification. PubChem records various stereoisomers of this naturally ocurring metabolite.
approved: f
ligand name: chaetocin
type: NaturalProductLigand

PBD150
canonical SMILES: COc1cc(ccc1OC)NC(=S)NCCCn1cncc1
isomeric SMILES: COc1cc(ccc1OC)NC(=S)NCCCn1cncc1
in ch i key: FZQXMGLQANXZRP-UHFFFAOYSA-N
in ch i: InChI=1S/C15H20N4O2S/c1-20-13-5-4-12(10-14(13)21-2)18-15(22)17-6-3-8-19-9-7-16-11-19/h4-5,7,9-11H,3,6,8H2,1-2H3,(H2,17,18,22)
comment: PBD150 is a potent inhibitor of glutaminyl cyclase (QC), an enzyme which can modify the N-terminal glutamate residue of amyloid beta (Aβ) proteins to generate pyroglutamate-Aβ <Reference id=27663/>.
iupac name: 3-(3,4-dimethoxyphenyl)-1-(3-imidazol-1-ylpropyl)thiourea
xref: CHEMBL201747
synonym: compound 53 [PMID 16420052]
approved: f
ligand name: PBD150
type: SyntheticOrganicLigand

EPZ005687
in ch i key: ZOIBZSZLMJDVDQ-UHFFFAOYSA-N
in ch i: InChI=1S/C32H37N5O3/c1-21-15-22(2)35-32(39)28(21)18-33-31(38)27-16-25(17-30-29(27)19-34-37(30)26-5-3-4-6-26)24-9-7-23(8-10-24)20-36-11-13-40-14-12-36/h7-10,15-17,19,26H,3-6,11-14,18,20H2,1-2H3,(H,33,38)(H,35,39)
comment: EPZ005687 is an inhibitor of the histone methyltransferase, enhancer of zeste 2 polycomb repressive complex 2 subunit (EZH2) <Reference id=27789/>.
iupac name: 1-cyclopentyl-N-[(4,6-dimethyl-2-oxo-1H-pyridin-3-yl)methyl]-6-[4-(morpholin-4-ylmethyl)phenyl]indazole-4-carboxamide
synonym: EPZ-005687
synonym: EPZ 005687
approved: f
ligand name: EPZ005687
type: SyntheticOrganicLigand

LTK-14
in ch i key: GEMUMPJYCDKSDU-OAKZDBKWSA-N
in ch i: InChI=1S/C39H52O6/c1-23(2)12-15-27-21-38-22-28(16-13-24(3)4)37(9,10)45-34(38)31(32(41)26-14-17-30(44-11)29(40)20-26)33(42)39(35(38)43,36(27,7)8)19-18-25(5)6/h12-14,17-18,20,27-28,40H,15-16,19,21-22H2,1-11H3/t27-,28+,38+,39+/m1/s1
comment: LTK-14 is a derivative of the natural product <Ligand id=7001/>. The structure was drawn from the image in <Reference id=27788/>, in which the compound is described as a selective inhibitor of histone acetyltransferase p300 (eq. K(lysine) acetyltransferase 2B, KAT2B- also known as p300/CBP-associated factor).
iupac name: (1S,3S,9R,11R)-7-(3-hydroxy-4-methoxybenzoyl)-4,4,10,10-tetramethyl-3,9,11-tris(3-methylbut-2-en-1-yl)-5-oxatricyclo[7.3.1.01,6]tridec-6-ene-8,13-dione
synonym: 14-methoxy IG (isogarcinol)
synonym: LTK14
approved: f
ligand name: LTK-14
type: SyntheticOrganicLigand

compound 4 [PMID: 25259874]
in ch i key: OVJFQPIFXZBDKN-IBGZPJMESA-N
in ch i: InChI=1S/C22H28N4O3S/c23-22(24)25-13-7-12-19(21(28)29)26-20(27)15-30-14-18(16-8-3-1-4-9-16)17-10-5-2-6-11-17/h1-6,8-11,18-19H,7,12-15H2,(H,26,27)(H,28,29)(H4,23,24,25)/t19-/m0/s1
iupac name: (2S)-5-(diaminomethylideneamino)-2-[[2-(2,2-diphenylethylsulfanyl)acetyl]amino]pentanoic acid
approved: f
ligand name: compound 4 [PMID: 25259874]
type: SyntheticOrganicLigand

bimiralisib
in ch i key: ADGGYDAFIHSYFI-UHFFFAOYSA-N
in ch i: InChI=1S/C17H20F3N7O2/c18-17(19,20)12-9-13(21)22-10-11(12)14-23-15(26-1-5-28-6-2-26)25-16(24-14)27-3-7-29-8-4-27/h9-10H,1-8H2,(H2,21,22)
comment: Bimiralisib (PQR309) is a novel dual inhibitor of phosphoinositol 3-kinase (PI3K) and mechanistic target of rapamycin (mTOR) kinases, with expected utility as an anti-cancer agent (see AACR poster #2664, 2015). The discovery of PQR309 is claimed in patent WO-2010052569-A2, where it is compound 54 (in structure tables) and Example P11 <Reference id=27778/>.
iupac name: 5-[bis(morpholin-4-yl)-1,3,5-triazin-2-yl]-4-(trifluoromethyl)pyridin-2-amine
synonym: PQR309
synonym: PQR-309
approved: f
ligand name: bimiralisib
type: SyntheticOrganicLigand

VS-5584
in ch i key: QYBGBLQCOOISAR-UHFFFAOYSA-N
in ch i: InChI=1S/C17H22N8O/c1-10(2)25-11(3)21-14-13(12-8-19-16(18)20-9-12)22-17(23-15(14)25)24-4-6-26-7-5-24/h8-10H,4-7H2,1-3H3,(H2,18,19,20)
comment: VS-5584 (SB2343) is a potent and selective dual PI3K (phosphatidylinositol 3-kinase)/mTOR (mechanistic target of rapamycin) kinase inhibitor <Reference id=27775/>.
iupac name: 5-(8-methyl-2-morpholin-4-yl-9-propan-2-ylpurin-6-yl)pyrimidin-2-amine
synonym: VS5584
synonym: SB2343
synonym: SB-2343
synonym: SB 2343
synonym: VS 5584
approved: f
ligand name: VS-5584
type: SyntheticOrganicLigand

compound 21 [PMID: 25259874]
in ch i key: RFBOIZXPIAOMAX-SFHVURJKSA-N
in ch i: InChI=1S/C24H28N6O3/c1-15-20(22(31)29-18(23(32)33)13-8-14-27-24(25)26)30-21(28-15)19(16-9-4-2-5-10-16)17-11-6-3-7-12-17/h2-7,9-12,18-19H,8,13-14H2,1H3,(H,28,30)(H,29,31)(H,32,33)(H4,25,26,27)/t18-/m0/s1
approved: f
ligand name: compound 21 [PMID: 25259874]
type: SyntheticOrganicLigand

SQ007-5
in ch i key: CZCSLPSTPNFNFR-WILIORGOSA-N
approved: f
ligand name: SQ007-5
type: PeptideLigand

tafamidis
canonical SMILES: Clc1cc(Cl)cc(c1)c1nc2c(o1)cc(cc2)C(=O)O
isomeric SMILES: Clc1cc(Cl)cc(c1)c1nc2c(o1)cc(cc2)C(=O)O
in ch i key: TXEIIPDJKFWEEC-UHFFFAOYSA-N
in ch i: InChI=1S/C14H7Cl2NO3/c15-9-3-8(4-10(16)6-9)13-17-11-2-1-7(14(18)19)5-12(11)20-13/h1-6H,(H,18,19)
comment: Tafamidis binds potently and selectively to transthyretin (TTR), stabilising protein tetramers, thereby inhibiting the formation of amyloid fibrils <Reference id=27766/>. The trade name for this drug is Vyndaqel which contains tafamidis meglumine (PubChem CID 24970412). The Vyndamax brand contains tafamidis parent molecule.
iupac name: 2-(3,5-dichlorophenyl)-1,3-benzoxazole-6-carboxylic acid
xref: CHEMBL2103837
synonym: FX-1006
synonym: Vyndaqel®
synonym: Vyndamax®
approved: t
ligand name: tafamidis
type: SyntheticOrganicLigand

PF-00489791
in ch i key: ZUHZNKJIJDAJFD-UHFFFAOYSA-N
in ch i: InChI=1S/C20H28N8O4S/c1-6-27(4)20-23-15-16(19(29)26-33(5,30)31)25-28(10-11-32-7-2)17(15)18(24-20)22-14-12-13(3)8-9-21-14/h8-9,12H,6-7,10-11H2,1-5H3,(H,26,29)(H,21,22,23,24)
comment: PF-00489791 is a long-acting, selective and competitive inhibitor of phosphodiesterase 5 (gene symbol PDE5A) inhibitor which is reported to reduce systemic blood pressure in patients with hypertension <Reference id=27761/>.
iupac name: 1-(2-ethoxyethyl)-5-(ethyl-methylamino)-7-[(4-methylpyridin-2-yl)amino]-N-methylsulfonylpyrazolo[5,4-e]pyrimidine-3-carboxamide
synonym: PF-489791
synonym: PF-489,791
approved: f
ligand name: PF-00489791
type: SyntheticOrganicLigand

ertugliflozin
in ch i key: MCIACXAZCBVDEE-CUUWFGFTSA-N
in ch i: InChI=1S/C22H25ClO7/c1-2-28-16-6-3-13(4-7-16)9-14-10-15(5-8-17(14)23)22-20(27)18(25)19(26)21(11-24,30-22)12-29-22/h3-8,10,18-20,24-27H,2,9,11-12H2,1H3/t18-,19-,20+,21-,22-/m0/s1
comment: Ertugliflozin (PF-04971729) is an inhibitor of sodium/glucose cotransporter 2 (SGLT2). The discovery of PF-04971729 is reported in <Reference id=27760/>, where it is compound 4.
iupac name: (1S,2S,3S,4R,5S)-5-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-1-(hydroxymethyl)-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triol
xref: CHEMBL1770248
synonym: Steglatro®
synonym: PF-04971729
synonym: MK-8835
approved: t
ligand name: ertugliflozin
type: SyntheticOrganicLigand

compound 1 [PMID: 25719566]
in ch i key: OAPIWVHFYSEARE-UHFFFAOYSA-N
in ch i: InChI=1S/C21H18N6/c1-16-14-27(25-24-16)12-11-26-15-23-20(18-5-3-2-4-6-18)21(26)19-9-7-17(13-22)8-10-19/h2-10,14-15H,11-12H2,1H3
iupac name: 4-[3-[2-(4-methyltriazol-1-yl)ethyl]-5-phenylimidazol-4-yl]benzonitrile
approved: f
ligand name: compound 1 [PMID: 25719566]
type: SyntheticOrganicLigand

GSK1070916
in ch i key: QTBWCSQGBMPECM-UHFFFAOYSA-N
in ch i: InChI=1S/C30H33N7O/c1-6-37-19-26(28(34-37)21-10-12-23(13-11-21)32-30(38)36(4)5)24-14-15-31-29-25(24)17-27(33-29)22-9-7-8-20(16-22)18-35(2)3/h7-17,19H,6,18H2,1-5H3,(H,31,33)(H,32,38)
comment: GSK1070916 is reported to be an ATP-competitive, potent and selective inhibitor of Aurora kinases B and C <Reference id=27671/>.
iupac name: 3-[4-[4-[2-[3-[(dimethylamino)methyl]phenyl]-1H-pyrrolo[2,3-b]pyridin-4-yl]-1-ethylpyrazol-3-yl]phenyl]-1,1-dimethylurea
xref: CHEMBL1090479
synonym: GSK-1070916
synonym: GSK 1070916
synonym: compound 17k [PMID 20420387]
approved: f
ligand name: GSK1070916
type: SyntheticOrganicLigand

etelcalcetide
in ch i key: ANIAZGVDEUQPRI-ZJQCGQFWSA-N
comment: Etelcalcetide is a novel calcimimetic, peptidic agonist of the human cell surface calcium-sensing receptor (CaSR) <Reference id=27755/>. The chemical structure shown here was generated using the SMILES from PubChem CID 71511839.
xref: CHEMBL3545184
synonym: velcalcetide
synonym: KAI-4169
synonym: AMG-416
synonym: AMG 416
synonym: Parsabiv®
approved: t
ligand name: etelcalcetide
type: PeptideLigand

olodanrigan
in ch i key: GHBCIXGRCZIPNQ-MHZLTWQESA-N
in ch i: InChI=1S/C32H29NO5/c1-37-28-18-17-25-20-33(31(34)29(23-13-7-3-8-14-23)24-15-9-4-10-16-24)27(32(35)36)19-26(25)30(28)38-21-22-11-5-2-6-12-22/h2-18,27,29H,19-21H2,1H3,(H,35,36)/t27-/m0/s1
comment: Olodanrigan (EMA401) is reported as a selective antagonist of the angiotensin type II receptor (AT2R) <Reference id=27739/><Reference id=27749/>. The compound is being assessed as a novel therapy for neuropathic pain <Reference id=27740/>. Note that PubChem CID 23683656 refers to the potassium salt and that the sodium salt was used in <Reference id=27749/>.
iupac name: (3S)-2-(2,2-diphenylacetyl)-6-methoxy-5-phenylmethoxy-3,4-dihydro-1H-isoquinoline-3-carboxylic acid
xref: CHEMBL34124
synonym: [S]-enantiomer of PD-126,055
synonym: [S]-enantiomer of EMA400
synonym: EMA401
synonym: EMA-401
approved: f
ligand name: olodanrigan
type: SyntheticOrganicLigand

vacquinol-1
in ch i key: VKLJPGAHSLIQKH-UHFFFAOYSA-N
in ch i: InChI=1S/C21H21ClN2O/c22-15-10-8-14(9-11-15)20-13-17(16-5-1-2-6-18(16)24-20)21(25)19-7-3-4-12-23-19/h1-2,5-6,8-11,13,19,21,23,25H,3-4,7,12H2
comment: We represent this molecule with no stereochemical assignments to represent the racemic mixture ariisng from the presence of two steroecentres. The compound can exist as RS (PubChem CID 36691047), SR (PubChem CID 36691042), RR (PubChem CID 36691044) or SS (PubChem CID 3246043) enantiomers. The compound is contained in the National Cancer Institute (NCI) Diversity Set II which is a freely accessible compound repository maintained as part of the Developmental Therapeutics Program (DTP). The DTP provides online, open access to screening data and compound structural details for small molecules that may be of use in anti-cancer (and anti-HIV) drug discovery programmes.
iupac name: [2-(4-chlorophenyl)quinolin-4-yl]-piperidin-2-ylmethanol
xref: CHEMBL1393664
synonym: NSC13316
approved: f
ligand name: vacquinol-1
type: SyntheticOrganicLigand

(-)-englerin A
in ch i key: GACOFEKSDCOVMV-RRYXBOBMSA-N
in ch i: InChI=1S/C26H34O6/c1-16(2)26-14-20(30-22(29)15-27)25(4,32-26)19-12-10-17(3)23(19)24(26)31-21(28)13-11-18-8-6-5-7-9-18/h5-9,11,13,16-17,19-20,23-24,27H,10,12,14-15H2,1-4H3/b13-11+/t17-,19-,20-,23-,24+,25+,26-/m1/s1
comment: (-)-englerin A is a plant extract from the bark of Phyllanthus engleri <Reference id=27734/>. (-)-englerin A is a potent and selective agonist of TRPC4 and TRPC5 calcium channels <Reference id=27733/> with cytotoxic activity selective for several renal cancer cell lines <Reference id=27734/>. The (+) enantiomer is inactive against the same cells <Reference id=27735/>. The compound has been chemically synthesised <Reference id=27735/><Reference id=27736/><Reference id=27737/>.
approved: f
ligand name: (-)-englerin A
type: SyntheticOrganicLigand

(-)-stepholidine
in ch i key: JKPISQIIWUONPB-HNNXBMFYSA-N
in ch i: InChI=1S/C19H21NO4/c1-23-18-8-12-5-6-20-10-14-11(3-4-16(21)19(14)24-2)7-15(20)13(12)9-17(18)22/h3-4,8-9,15,21-22H,5-7,10H2,1-2H3/t15-/m0/s1
comment: (−)-stepholidine is a pan-dopamine receptor antagonist <Reference id=26594/>.
iupac name: (13aS)-3,9-dimethoxy-6,8,13,13a-tetrahydro-5H-isoquinolino[2,1-b]isoquinoline-2,10-diol
xref: CHEMBL487387
synonym: S-stepholidine
synonym: L-stepholidine
approved: f
ligand name: (-)-stepholidine
type: SyntheticOrganicLigand

MLS1547
in ch i key: OPEJNANYABTIGC-UHFFFAOYSA-N
in ch i: InChI=1S/C19H19ClN4O/c20-16-12-14(19(25)18-15(16)4-3-7-22-18)13-23-8-10-24(11-9-23)17-5-1-2-6-21-17/h1-7,12,25H,8-11,13H2
comment: MLS1547 is reported to be a G protein biased dopamine D2 receptor agonist <Reference id=27716/>. The compound antagonises arrestin recruitment to the dopamine-induced D2 receptor, but behaves as an agonist in its capacity to induce G protein signalling (ie inhibition of cAMP accumulation via Gi).
iupac name: 5-chloro-7-[(4-pyridin-2-ylpiperazin-1-yl)methyl]quinolin-8-ol
xref: CHEMBL1606583
synonym: MLS000051547
approved: f
ligand name: MLS1547
type: SyntheticOrganicLigand

ML321
in ch i key: YXLLQNMKIDBOGH-NDEPHWFRSA-N
in ch i: InChI=1S/C21H18N2O3S2/c1-23-17-13-14(20(24)22-11-10-15-5-4-12-27-15)8-9-19(17)28(26)18-7-3-2-6-16(18)21(23)25/h2-9,12-13H,10-11H2,1H3,(H,22,24)/t28-/m0/s1
comment: ML321 is a dopamine D2 receptor selective antagonist <Reference id=25059/> which is a suitable tool compound for the dissection of D2 receptor modulation in proof-of-concept animal studies and provides medicinal chemists a lead structure for the development of novel D2 receptor selective drugs.
iupac name: (11S)-5-methyl-6,11-dioxo-N-(2-thiophen-2-ylethyl)benzo[b][1,4]benzothiazepine-3-carboxamide
xref: CHEMBL3234544
synonym: compound 65 [PMID 24666157]
approved: f
ligand name: ML321
type: SyntheticOrganicLigand

tacedinaline
canonical SMILES: CC(=O)Nc1ccc(cc1)C(=O)Nc1ccccc1N
isomeric SMILES: CC(=O)Nc1ccc(cc1)C(=O)Nc1ccccc1N
in ch i key: VAZAPHZUAVEOMC-UHFFFAOYSA-N
in ch i: InChI=1S/C15H15N3O2/c1-10(19)17-12-8-6-11(7-9-12)15(20)18-14-5-3-2-4-13(14)16/h2-9H,16H2,1H3,(H,17,19)(H,18,20)
comment: Tacedinaline inhibits the histone deacetylase enzyme HDAC1 <Reference id=27711/>, and is reported to have antitumour activity in preclinical studies <Reference id=27708/><Reference id=27710/><Reference id=27709/>.
iupac name: 4-acetamido-N-(2-aminophenyl)benzamide
xref: CHEMBL235191
synonym: CI-994
synonym: CI994
approved: f
ligand name: tacedinaline
type: SyntheticOrganicLigand

abexinostat
in ch i key: MAUCONCHVWBMHK-UHFFFAOYSA-N
in ch i: InChI=1S/C21H23N3O5/c1-24(2)13-17-16-5-3-4-6-18(16)29-19(17)21(26)22-11-12-28-15-9-7-14(8-10-15)20(25)23-27/h3-10,27H,11-13H2,1-2H3,(H,22,26)(H,23,25)
comment: Abexinostat is an investigational inhibitor of histone deacetylase enzymes (HDACs), with antitumour activity <Reference id=27707/>.
iupac name: 3-(dimethylaminomethyl)-N-[2-[4-(hydroxycarbamoyl)phenoxy]ethyl]-1-benzofuran-2-carboxamide
xref: CHEMBL2103863
synonym: CRA-24781
synonym: PCI-24781
synonym: PCI24781
synonym: PCI 24781
synonym: CRA-024781
synonym: CRA 024781
synonym: CRA024781
approved: f
ligand name: abexinostat
type: SyntheticOrganicLigand

pracinostat
isomeric SMILES: CCCCc1nc2c(n1CCN(CC)CC)ccc(c2)/C=C/C(=O)NO
in ch i key: JHDKZFFAIZKUCU-ZRDIBKRKSA-N
in ch i: InChI=1S/C20H30N4O2/c1-4-7-8-19-21-17-15-16(10-12-20(25)22-26)9-11-18(17)24(19)14-13-23(5-2)6-3/h9-12,15,26H,4-8,13-14H2,1-3H3,(H,22,25)/b12-10+
comment: Pracinostat is an orally available, potent pan-HDAC inhibitor <Reference id=27704/>.
iupac name: (2E)-3-{2-butyl-1-[2-(diethylamino)ethyl]-1H-1,3-benzodiazol-5-yl}-N-hydroxyprop-2-enamide
xref: CHEMBL1851943
synonym: SB-939
synonym: SB939
synonym: SB 939
approved: f
ligand name: pracinostat
type: SyntheticOrganicLigand

itacitinib
in ch i key: KTBSXLIQKWEBRB-UHFFFAOYSA-N
in ch i: InChI=1S/C26H23F4N9O/c27-20-18(1-7-32-22(20)26(28,29)30)24(40)37-9-3-17(4-10-37)38-13-25(14-38,5-6-31)39-12-16(11-36-39)21-19-2-8-33-23(19)35-15-34-21/h1-2,7-8,11-12,15,17H,3-5,9-10,13-14H2,(H,33,34,35)
comment: Itacitinib (INCB039110) is a potent and selective inhibitor of Janus kinase 1 (JAK1). Design and synthesis of this compound is claimed in patent WO2011112662 where it is Example 294 <Reference id=27703/>.
iupac name: 2-[1-[1-[3-fluoro-2-(trifluoromethyl)pyridine-4-carbonyl]piperidin-4-yl]-3-[4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]azetidin-3-yl]acetonitrile
synonym: Examlpe 294 [WO2011112662]
synonym: INCB-039110
approved: f
ligand name: itacitinib
type: SyntheticOrganicLigand

elagolix
in ch i key: HEAUOKZIVMZVQL-VWLOTQADSA-N
in ch i: InChI=1S/C32H30F5N3O5/c1-19-28(21-11-6-14-26(45-2)29(21)34)30(43)40(18-25(20-9-4-3-5-10-20)38-16-8-15-27(41)42)31(44)39(19)17-22-23(32(35,36)37)12-7-13-24(22)33/h3-7,9-14,25,38H,8,15-18H2,1-2H3,(H,41,42)/t25-/m0/s1
comment: Elagolix is a non-peptide gonadotrophin receptor (GnRHR) antagonist <Reference id=27697/>. As of July 2018, it is the first and only FDA-approved oral GnRH antagonist available for the treatment of moderate to severe endometriosis pain.
iupac name: 4-[[(1R)-2-[5-(2-fluoro-3-methoxyphenyl)-3-[[2-fluoro-6-(trifluoromethyl)phenyl]methyl]-4-methyl-2,6-dioxopyrimidin-1-yl]-1-phenylethyl]amino]butanoic acid
xref: CHEMBL1208155
synonym: NBI-56418
synonym: NBI 56418
synonym: NBI56418
synonym: compound 10b [PMID 19006286]
synonym: Orilissa®
approved: t
ligand name: elagolix
type: SyntheticOrganicLigand

iniparib
canonical SMILES: [O-][N+](=O)c1cc(ccc1I)C(=O)N
isomeric SMILES: [O-][N+](=O)c1cc(ccc1I)C(=O)N
in ch i key: MDOJTZQKHMAPBK-UHFFFAOYSA-N
in ch i: InChI=1S/C7H5IN2O3/c8-5-2-1-4(7(9)11)3-6(5)10(12)13/h1-3H,(H2,9,11)
comment: Iniparib was reported as PARP1 inhibitor <Reference id=27684/> (or rather its metabolite 4-iodo-3-nitrosobenzamide was reported to inhibit PARP1 activity), however this action has been disputed <Reference id=27682/><Reference id=27683/>.
iupac name: 4-iodo-3-nitrobenzamide
synonym: SAR240550
synonym: BSI-201
synonym: BSI201
synonym: BSI 201
approved: f
ligand name: iniparib
type: SyntheticOrganicLigand

birabresib
in ch i key: GNMUEVRJHCWKTO-FQEVSTJZSA-N
comment: OTX015 inhibits interaction between bromodomain and extra-terminal (BET) family of bromodomain-containing proteins (BRDs) BET domains and acetylated histone 4 (AcH4). It is an orally available novel BRD2/3/4 inhibitor with potent preclinical anti-tumour activity <Reference id=32095/><Reference id=32096/><Reference id=32097/><Reference id=32098/><Reference id=32099/><Reference id=32100/>. OTX015 is an analogue of <Ligand id=7511/>.
iupac name: 2-[(6S)-4-(4-chlorophenyl)-2,3,9-trimethyl-6H-thieno[3,2-f]-[1, 2, 4] triazolo [4,3-a] [1, 4] diazepin-6-yl]-N-(4-hydroxyphenyl)-acetamide dehydrate
synonym: OTX015
synonym: OTX-015
synonym: MK-8628
approved: f
ligand name: birabresib
type: SyntheticOrganicLigand

L-valinol
canonical SMILES: OCC(C(C)C)N
isomeric SMILES: OC[C@H](C(C)C)N
in ch i key: NWYYWIJOWOLJNR-RXMQYKEDSA-N
in ch i: InChI=1S/C5H13NO/c1-4(2)5(6)3-7/h4-5,7H,3,6H2,1-2H3/t5-/m1/s1
iupac name: (2S)-2-amino-3-methylbutan-1-ol
approved: f
ligand name: L-valinol
type: SyntheticOrganicLigand

compound 46 [PMID: 16451062]
in ch i key: QNJAKUMXJFWQOG-UHFFFAOYSA-N
in ch i: InChI=1S/C29H33FN6O4S/c1-39-25-14-23-24(15-26(25)40-11-3-8-36-9-6-19(17-37)7-10-36)32-18-33-28(23)35-29-31-16-22(41-29)13-27(38)34-21-5-2-4-20(30)12-21/h2,4-5,12,14-16,18-19,37H,3,6-11,13,17H2,1H3,(H,34,38)(H,31,32,33,35)
comment: Compound 46 is a modified analogue of <Ligand id=8353/>, with improved affinity for Aurora kinases A and B <Reference id=27660/>.
iupac name: N-(3-fluorophenyl)-2-[2-[[7-[3-[4-(hydroxymethyl)piperidin-1-yl]propoxy]-6-methoxyquinazolin-4-yl]amino]-1,3-thiazol-5-yl]acetamide
xref: CHEMBL201307
approved: f
ligand name: compound 46 [PMID: 16451062]
type: SyntheticOrganicLigand

hesperadin
isomeric SMILES: CCS(=O)(=O)Nc1ccc2c(c1)/C(=C(/c1ccccc1)/Nc1ccc(cc1)CN1CCCCC1)/C(=O)N2
in ch i key: GLDSKRNGVVYJAB-DQSJHHFOSA-N
in ch i: InChI=1S/C29H32N4O3S/c1-2-37(35,36)32-24-15-16-26-25(19-24)27(29(34)31-26)28(22-9-5-3-6-10-22)30-23-13-11-21(12-14-23)20-33-17-7-4-8-18-33/h3,5-6,9-16,19,30,32H,2,4,7-8,17-18,20H2,1H3,(H,31,34)/b28-27-
comment: Hesperadin is an Aurora kinase B inhibitor <Reference id=27659/>.
iupac name: N-[(3Z)-2-oxo-3-[phenyl-[[4-(piperidin-1-ylmethyl)phenyl]amino]methylidene]-1H-indol-5-yl]ethanesulfonamide
xref: CHEMBL514409
approved: f
ligand name: hesperadin
type: SyntheticOrganicLigand

ZM447439
in ch i key: OGNYUTNQZVRGMN-UHFFFAOYSA-N
in ch i: InChI=1S/C29H31N5O4/c1-36-26-18-24-25(19-27(26)38-15-5-12-34-13-16-37-17-14-34)30-20-31-28(24)32-22-8-10-23(11-9-22)33-29(35)21-6-3-2-4-7-21/h2-4,6-11,18-20H,5,12-17H2,1H3,(H,33,35)(H,30,31,32)
comment: ZM447439 is an inhibitor of Aurora kinases A and B <Reference id=27658/>.
iupac name: N-[4-[[6-methoxy-7-(3-morpholin-4-ylpropoxy)quinazolin-4-yl]amino]phenyl]benzamide
xref: CHEMBL202721
synonym: ZM 447439
synonym: ZM-447439
approved: f
ligand name: ZM447439
type: SyntheticOrganicLigand

candesartan cilexetil
in ch i key: GHOSNRCGJFBJIB-UHFFFAOYSA-N
in ch i: InChI=1S/C33H34N6O6/c1-3-42-32-34-28-15-9-14-27(31(40)43-21(2)44-33(41)45-24-10-5-4-6-11-24)29(28)39(32)20-22-16-18-23(19-17-22)25-12-7-8-13-26(25)30-35-37-38-36-30/h7-9,12-19,21,24H,3-6,10-11,20H2,1-2H3,(H,35,36,37,38)
iupac name: 1-cyclohexyloxycarbonyloxyethyl 2-ethoxy-3-[[4-[2-(2H-tetrazol-5-yl)phenyl]phenyl]methyl]benzimidazole-4-carboxylate
xref: CHEMBL1014
approved: f
ligand name: candesartan cilexetil
type: SyntheticOrganicLigand

sotagliflozin
in ch i key: QKDRXGFQVGOQKS-CRSSMBPESA-N
in ch i: InChI=1S/C21H25ClO5S/c1-3-26-15-7-4-12(5-8-15)10-14-11-13(6-9-16(14)22)20-18(24)17(23)19(25)21(27-20)28-2/h4-9,11,17-21,23-25H,3,10H2,1-2H3/t17-,18-,19+,20+,21-/m1/s1
comment: Sotagliflozin is a dual inhibitor of the sodium/glucose cotransporters 1 and 2 (SGLT1/2) <Reference id=27457/><Reference id=27458/>.
iupac name: (2S,3R,4R,5S,6R)-2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6-methylsulfanyloxane-3,4,5-triol
xref: CHEMBL3039507
synonym: LX-4211
synonym: LX 4211
synonym: LX4211
synonym: Zynquista®
approved: t
ligand name: sotagliflozin
type: SyntheticOrganicLigand

fadrozole
canonical SMILES: N#Cc1ccc(cc1)C1CCCc2n1cnc2
isomeric SMILES: N#Cc1ccc(cc1)C1CCCc2n1cnc2
in ch i key: CLPFFLWZZBQMAO-UHFFFAOYSA-N
in ch i: InChI=1S/C14H13N3/c15-8-11-4-6-12(7-5-11)14-3-1-2-13-9-16-10-17(13)14/h4-7,9-10,14H,1-3H2
comment: Fadrozole was designed and reported as a selective aromatase (CYP19A1) inhibitor having only weak effects on aldosterone and cortisol production <Reference id=27455/>. More recent evidence suggests that fadrozole is in fact a potent inhibitor of the cytochrome P450 enzymes, CYP11B1 (11-beta-hydroxylase) and CYP11B2 (aldosterone synthase) responsible for cortisol and aldosterone synthesis respectively <Reference id=27454/>.
iupac name: 4-(5,6,7,8-tetrahydroimidazo[5,1-f]pyridin-5-yl)benzonitrile
xref: CHEMBL9298
synonym: FAD-286
synonym: CGS-16949A
synonym: FAD 286
synonym: FAD286
synonym: CGS 16949 A
synonym: Afema®
synonym: CGS16949A
approved: t
ligand name: fadrozole
type: SyntheticOrganicLigand

A(4-24)(F23A)H2
in ch i key: JPICFXXNKSFHNE-FHWINVSDSA-N
comment: Synthetic analogue of the A chain of human relaxin.
approved: f
ligand name: A(4-24)(F23A)H2
type: PeptideLigand

P8 [PMID: 25923432]
in ch i key: ASNYBKBWOJOFFP-CPDXTSBQSA-N
in ch i: InChI=1S/C35H53N7O20/c1-15(2)13-22(35(61)62)42-33(59)20(7-12-27(51)52)39-31(57)18(5-10-25(47)48)40-34(60)21(14-28(53)54)41-32(58)19(6-11-26(49)50)38-30(56)17(4-9-24(45)46)37-29(55)16(36)3-8-23(43)44/h15-22H,3-14,36H2,1-2H3,(H,37,55)(H,38,56)(H,39,57)(H,40,60)(H,41,58)(H,42,59)(H,43,44)(H,45,46)(H,47,48)(H,49,50)(H,51,52)(H,53,54)(H,61,62)/t16-,17-,18-,19-,20-,21-,22-/m0/s1
comment: This small peptide represents amino acids 67-73 of presenilin 1. The peptide is water soluble <Reference id=27639/>.
approved: f
ligand name: P8 [PMID: 25923432]
type: PeptideLigand

P4 [PMID: 25923432]
in ch i key: UGSPCJRSHHDBMB-OEAGQSEASA-N
in ch i: InChI=1S/C58H93N19O19/c1-29(2)19-35(71-47(85)32(59)26-78)48(86)65-25-45(82)69-38(21-31-23-63-28-67-31)56(94)76-17-7-10-40(76)52(90)70-34(13-14-46(83)84)55(93)75-16-6-11-41(75)53(91)73-36(20-30(3)4)50(88)74-39(27-79)51(89)72-37(22-43(60)80)49(87)66-24-44(81)68-33(9-5-15-64-58(61)62)54(92)77-18-8-12-42(77)57(95)96/h23,28-30,32-42,78-79H,5-22,24-27,59H2,1-4H3,(H2,60,80)(H,63,67)(H,65,86)(H,66,87)(H,68,81)(H,69,82)(H,70,90)(H,71,85)(H,72,89)(H,73,91)(H,74,88)(H,83,84)(H,95,96)(H4,61,62,64)/t32-,33-,34-,35-,36-,37-,38-,39-,40-,41-,42-/m0/s1
comment: This small peptide represents amino acids 43–55 of presenilin 1. The peptide is water soluble <Reference id=27639/>.
approved: f
ligand name: P4 [PMID: 25923432]
type: PeptideLigand

135PAM1
in ch i key: FAXDMTURZKFXIY-UHFFFAOYSA-N
iupac name: 3-[3,5-bis(trifluoromethyl)phenyl]-1-[(3,4-dichlorophenyl)methyl]-1-[2-(5-methoxy-1H-indol-3-yl)ethyl]urea
approved: f
ligand name: 135PAM1
type: SyntheticOrganicLigand

azeliragon
in ch i key: KJNNWYBAOPXVJY-UHFFFAOYSA-N
in ch i: InChI=1S/C32H38ClN3O2/c1-4-7-9-32-34-31(25-10-16-28(17-11-25)37-23-8-22-35(5-2)6-3)24-36(32)27-14-20-30(21-15-27)38-29-18-12-26(33)13-19-29/h10-21,24H,4-9,22-23H2,1-3H3
comment: Azeliragon is an orally bioavailable small molecule that inhibits the receptor for advanced glycation endproducts (RAGE) <Reference id=27478/><Reference id=27485/>.
iupac name: 3-[4-[2-butyl-1-[4-(4-chlorophenoxy)phenyl]imidazol-4-yl]phenoxy]-N,N-diethylpropan-1-amine
synonym: TTP488
approved: f
ligand name: azeliragon
type: SyntheticOrganicLigand

polmacoxib
in ch i key: IJWPAFMIFNSIGD-UHFFFAOYSA-N
in ch i: InChI=1S/C18H16FNO4S/c1-18(2)17(21)15(12-4-3-5-13(19)10-12)16(24-18)11-6-8-14(9-7-11)25(20,22)23/h3-10H,1-2H3,(H2,20,22,23)
comment: Polmacoxib is a first-in-class dual COX2/carbonic anhydrase I/II inhibitor, a potential non-steroidal anti-inflammatory drug (NSAID) with postulated attenuated cardiovascular risk compared to selective COX2 inhibiting NSAIDs <Reference id=27468/>.
iupac name: 4-[3-(3-fluorophenyl)-5,5-dimethyl-4-oxofuran-2-yl]benzenesulfonamide
xref: CHEMBL166863
synonym: CG100649
synonym: CG-100649
synonym: CG 100649
synonym: Acelex® (S. Korea)
approved: t
ligand name: polmacoxib
type: SyntheticOrganicLigand

A(10-24)INSL3
in ch i key: ORZUJWXQUJEDHD-VGYPRHCQSA-N
comment: Synthetic analogue of the A chain of human INSL3.
approved: f
ligand name: A(10-24)INSL3
type: PeptideLigand

osilodrostat
canonical SMILES: N#Cc1ccc(c(c1)F)C1CCc2n1cnc2
isomeric SMILES: N#Cc1ccc(c(c1)F)[C@H]1CCc2n1cnc2
in ch i key: USUZGMWDZDXMDG-CYBMUJFWSA-N
in ch i: InChI=1S/C13H10FN3/c14-12-5-9(6-15)1-3-11(12)13-4-2-10-7-16-8-17(10)13/h1,3,5,7-8,13H,2,4H2/t13-/m1/s1
comment: Osilodrostat was designed as an inhibitor of aldosterone synthase (CYP11B2), but is also reported to inhibit the closely related enzyme, 11-beta-hydroxylase (CYP11B1) and hence as an inhibitor of cortisol biosynthesis <Reference id=27452/>. It is this latter action of osilodrostat that is harnessed for clinical utility in Cushing's disease. The drug is orally bioavailable.
iupac name: 4-[(5R)-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-5-yl]-3-fluorobenzonitrile
xref: CHEMBL3099695
synonym: Isturisa®
synonym: LCI699
synonym: LCI-699
approved: t
ligand name: osilodrostat
type: SyntheticOrganicLigand

decernotinib
in ch i key: ASUGUQWIHMTFJL-QGZVFWFLSA-N
in ch i: InChI=1S/C18H19F3N6O/c1-3-17(2,16(28)25-10-18(19,20)21)27-13-6-8-23-15(26-13)12-9-24-14-11(12)5-4-7-22-14/h4-9H,3,10H2,1-2H3,(H,22,24)(H,25,28)(H,23,26,27)/t17-/m1/s1
comment: Decernotinib is a selective inhibitor of Janus kinase 3 (JAK3) <Reference id=27444/>.
iupac name: (2R)-2-methyl-2-[[2-(1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-4-yl]amino]-N-(2,2,2-trifluoroethyl)butanamide
xref: CHEMBL3039513
synonym: VX-509
synonym: VX 509
synonym: VX509
synonym: VRT-831509
synonym: adelatinib
synonym: VRT 831509
approved: f
ligand name: decernotinib
type: SyntheticOrganicLigand

A(9-26)INSL3
in ch i key: HHIHBEIJOBMKLZ-XYUOUADWSA-N
comment: Synthetic analogue of the A chain of human INSL3.
approved: f
ligand name: A(9-26)INSL3
type: PeptideLigand

ZD-7155
in ch i key: BFVNEYDCFJNLGN-UHFFFAOYSA-N
in ch i: InChI=1S/C26H26N6O/c1-3-19-15-24-22(23(4-2)27-19)13-14-25(33)32(24)16-17-9-11-18(12-10-17)20-7-5-6-8-21(20)26-28-30-31-29-26/h5-12,15H,3-4,13-14,16H2,1-2H3,(H,28,29,30,31)
comment: ZD-7155 is an orally active antagonist of the angiotensin II type 1 receptor. It is more potent and longer-acting than the prototype AT1 antagonist, <Ligand id=590/> (in rats) <Reference id=27588/>. ZD-7155 has been co-crystalised with a modified human AT1 receptor with PDB structure ID 4YAY <Reference id=27930/>.
iupac name: 5,7-diethyl-1-[[4-[2-(2H-tetrazol-5-yl)phenyl]phenyl]methyl]-3,4-dihydro-1,6-naphthyridin-2-one
xref: CHEMBL159096
synonym: ZD7155
synonym: ZD 7155
approved: f
ligand name: ZD-7155
type: SyntheticOrganicLigand

ML290
in ch i key: RSYHJSDOGMSLDH-UHFFFAOYSA-N
synonym: ML 290
synonym: compound 8 [PMID: 23764525]
approved: f
ligand name: ML290
type: SyntheticOrganicLigand

bempedoic acid
in ch i key: HYHMLYSLQUKXKP-UHFFFAOYSA-N
in ch i: InChI=1S/C19H36O5/c1-18(2,16(21)22)13-9-5-7-11-15(20)12-8-6-10-14-19(3,4)17(23)24/h15,20H,5-14H2,1-4H3,(H,21,22)(H,23,24)
comment: Bempedoic acid (ETC-1002) is an orally delivered non-statin drug for treating dyslipidemia and related cardiovascular disease, which offers an additional pharmaceutical strategy for statin-refractory or statin-intolerant patients <Reference id=38860/><Reference id=38859/><Reference id=38857/>. Its novel mechanism of action makes it the first-in-class ATP citrate lyase (ACLY; P53396) inhibitor to reach the clinic <Reference id=38861/>. Bempedoic acid is in fact a prodrug, as it must be converted to its active metabolite bempedoic acid-CoA by endogenous liver acyl-CoA synthetase. Bempedoic acid-CoA is the bona fide ACLY inhibitor. ACLY is the primary enzyme responsible for the synthesis of cytosolic acetyl-CoA, which in turn is required for de novo lipogenesis and cholesterogenesis, and its inhibition directly reduces cholesterol synthesis in the liver <Reference id=38856/>.
iupac name: 8-hydroxy-2,2,14,14-tetramethylpentadecanedioic acid
xref: CHEMBL3545313
synonym: Nexletol®
synonym: ESP-55016
synonym: ETC-1002
synonym: Nilemdo®
approved: t
ligand name: bempedoic acid
type: SyntheticOrganicLigand

ABT-737
in ch i key: HPLNQCPCUACXLM-PGUFJCEWSA-N
comment: ABT-737 is an antagonist of prosurvival Bcl-2 family proteins <Reference id=27503/>, but has poor aqueous solubility.
iupac name: 4-[4-[[2-(4-chlorophenyl)phenyl]methyl]piperazin-1-yl]-N-[4-[[(2R)-4-dimethylamino-1-phenylsulfanylbutan-2-yl]amino]-3-nitrophenyl]sulfonylbenzamide
xref: CHEMBL376408
synonym: compound 2 [PMID 17256834]
synonym: ABT 737
synonym: ABT737
approved: f
ligand name: ABT-737
type: SyntheticOrganicLigand

navitoclax
in ch i key: JLYAXFNOILIKPP-KXQOOQHDSA-N
comment: Navitoclax is a potent and orally active BH3 mimetic which antagonises the action of Bcl-2 family proteins Bcl-2, Bcl-xL and Bcl-w <Reference id=27499/>. This compound is the result of medicinal chemistry effort to increase aqueous solubility of the parent compound <Ligand id=8320/>.
xref: CHEMBL443684
synonym: ABT-263
synonym: ABT 263
synonym: ABT263
approved: f
ligand name: navitoclax
type: SyntheticOrganicLigand

venetoclax
in ch i key: LQBVNQSMGBZMKD-UHFFFAOYSA-N
comment: Venetoclax is a BH3 mimetic that selectively targets Bcl-2 <Reference id=27496/>, utilised for its pro-apoptotic activity. It is noteworthy that venetoclax is the first approved medicine designed to induce a natural process that helps cells self-destruct. The IUPAC name provided by PubChem matches 'Example 5' claimed in patent US8580794 <Reference id=27495/>.
iupac name: 4-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohexen-1-yl]methyl]piperazin-1-yl]-N-[3-nitro-4-(oxan-4-ylmethylamino)phenyl]sulfonyl-2-(1H-pyrrolo[2,3-b]pyridin-5-yloxy)benzamide
xref: CHEMBL3137309
synonym: GDC-0199
synonym: ABT-199
synonym: Venclyxto®
synonym: Venclexta®
approved: t
ligand name: venetoclax
type: SyntheticOrganicLigand

peficitinib
in ch i key: DREIJXJRTLTGJC-JQCLMNFQSA-N
in ch i: InChI=1S/C18H22N4O2/c19-16(23)13-8-21-17-12(1-2-20-17)15(13)22-14-10-3-9-4-11(14)7-18(24,5-9)6-10/h1-2,8-11,14,24H,3-7H2,(H2,19,23)(H2,20,21,22)/t9?,10-,11+,14?,18?
comment: Peficitinib is an oral Janus kinase inhibitor <Reference id=27466/> that was developed for potential anti-inflammatory action in autoimmune diseases including rheumatoid arthritis <Reference id=41901/><Reference id=41899/>, psoriasis and ulcerative colitis <Reference id=41900/>.
iupac name: 4-[[(1R,3S)-5-hydroxy-2-adamantyl]amino]-1H-pyrrolo[2,3-b]pyridine-5-carboxamide
xref: CHEMBL3137308
synonym: ASP015K
synonym: JNJ-54781532
approved: t
ligand name: peficitinib
type: SyntheticOrganicLigand

esuberaprost
in ch i key: CTPOHARTNNSRSR-NOQAJONNSA-N
in ch i: InChI=1S/C24H30O5/c1-3-4-7-15(2)19(25)13-12-17-20(26)14-21-23(17)18-10-5-8-16(24(18)29-21)9-6-11-22(27)28/h5,8,10,12-13,15,17,19-21,23,25-26H,6-7,9,11,14H2,1-2H3,(H,27,28)/b13-12+/t15-,17-,19+,20+,21-,23-/m0/s1
comment: Esuberaprost is a defined enantiomer of the racemate <Ligand id=1967/> and represents the active enantiomer <Reference id=27464/>. Like beraprost, the compound is a prostacyclin IP1 receptor agonist.
xref: CHEMBL3137314
synonym: BPS-314d
synonym: APS-314D free acid
approved: f
ligand name: esuberaprost
type: SyntheticOrganicLigand

talazoparib
in ch i key: IUEWAGVJRJORLA-HZPDHXFCSA-N
in ch i: InChI=1S/C19H14F2N6O/c1-27-18(22-8-23-27)15-16(9-2-4-10(20)5-3-9)24-13-7-11(21)6-12-14(13)17(15)25-26-19(12)28/h2-8,15-16,25H,1H3,(H,26,28)/t15-,16-/m1/s1
comment: Talazoparib is a PARP inhibitor <Reference id=27461/>, inhibiting both PARP1 and PARP2 <Reference id=27461/><Reference id=27462/>. The compound is bioavailable as the tosylate salt (PubChem CID 56966514).
xref: CHEMBL3137320
synonym: BMN 673
synonym: BMN-673
synonym: Talzenna®
synonym: BMN673
approved: t
ligand name: talazoparib
type: SyntheticOrganicLigand

dasotraline
canonical SMILES: NC1CCC(c2c1cccc2)c1ccc(c(c1)Cl)Cl
in ch i key: SRPXSILJHWNFMK-MEDUHNTESA-N
in ch i: InChI=1S/C16H15Cl2N/c17-14-7-5-10(9-15(14)18)11-6-8-16(19)13-4-2-1-3-12(11)13/h1-5,7,9,11,16H,6,8,19H2/t11-,16+/m0/s1
comment: Dasotraline is a triple reuptake inhibitor <Reference id=27442/><Reference id=27443/>. Such compounds are also known as serotonin-norepinephrine-dopamine reuptake inhibitors, or SNDRIs. Structurally, dasotraline is a stereoisomer of an active metabolite of <Ligand id=4798/>, a selective serotonin reuptake inhibitor (SSRI) antidepressant.
iupac name: (1R,4S)-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydronaphthalen-1-amine
xref: CHEMBL3301595
synonym: (1R,4S)-trans-norsertraline
synonym: SEP-225289
synonym: SEP-225,289
approved: f
ligand name: dasotraline
type: SyntheticOrganicLigand

rivipansel
in ch i key: VXBNTHRZPJLRSS-PTCSXESPSA-N
comment: Rivipansel is a synthetic glycomimetic molecule, rationally designed as a pan-selectin inhibitor <Reference id=27440/>.
iupac name: (2S)-2-[(2R,3R,4S,5S,6R)-3-benzoyloxy-2-[(1R,2R,3S,5R)-3-[(2,4-dioxo-1H-pyrimidine-6-carbonyl)amino]-5-[2-[[2-[2-[2-oxo-2-[(3,6,8-trisulfonaphthalen-1-yl)amino]ethoxy]ethoxy]acetyl]amino]ethylcarbamoyl]-2-[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxycyclohexyl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-3-cyclohexylpropanoic acid
synonym: PF-0646003102
synonym: PF-06460031
synonym: GMI-1070
approved: f
ligand name: rivipansel
type: SyntheticOrganicLigand

compound 7 [PMID: 25719566]
in ch i key: YPRKVQKJNRKXFN-UHFFFAOYSA-N
in ch i: InChI=1S/C19H18N8/c1-14-11-27(24-23-14)8-7-26-13-21-18(17-10-22-25(2)12-17)19(26)16-5-3-15(9-20)4-6-16/h3-6,10-13H,7-8H2,1-2H3
approved: f
ligand name: compound 7 [PMID: 25719566]
type: SyntheticOrganicLigand

tucidinostat
in ch i key: WXHHICFWKXDFOW-UHFFFAOYSA-N
in ch i: InChI=1S/C22H19FN4O2/c23-18-8-9-19(24)20(12-18)27-22(29)17-6-3-16(4-7-17)14-26-21(28)10-5-15-2-1-11-25-13-15/h1-13H,14,24H2,(H,26,28)(H,27,29)
comment: Tucidinostat (chidamide) is an orally active inhibitor of histone deacetylase (HDAC) enzymes <Reference id=27433/>. It has some subtype selectivity for HDAC isoenzymes 1, 2, 3 and 10. Note that we show this compound with no specified stereochemistry.
iupac name: N-(2-amino-5-fluorophenyl)-4-{[3-(pyridin-3-yl)prop-2-enamido]methyl}benzamide
synonym: CS055
synonym: HBI-8000
synonym: CS-055
synonym: chidamide
approved: t
ligand name: tucidinostat
type: SyntheticOrganicLigand

compound 7d [PMID: 25703523]
canonical SMILES: COc1ccc(cc1c1nc(N)nc2c1[nH]cn2)Br
isomeric SMILES: COc1ccc(cc1c1nc(N)nc2c1[nH]cn2)Br
in ch i key: KDNVOUMYSICLPF-UHFFFAOYSA-N
in ch i: InChI=1S/C12H10BrN5O/c1-19-8-3-2-6(13)4-7(8)9-10-11(16-5-15-10)18-12(14)17-9/h2-5H,1H3,(H3,14,15,16,17,18)
iupac name: 6-(5-bromo-2-methoxyphenyl)-7H-purin-2-amine
approved: f
ligand name: compound 7d [PMID: 25703523]
type: SyntheticOrganicLigand

mirogabalin
canonical SMILES: CCC1=CC2C(C1)CC2(CN)CC(=O)O
isomeric SMILES: CCC1=C[C@@H]2[C@H](C1)C[C@]2(CN)CC(=O)O
in ch i key: FTBQORVNHOIASH-CKYFFXLPSA-N
in ch i: InChI=1S/C12H19NO2/c1-2-8-3-9-5-12(7-13,6-11(14)15)10(9)4-8/h4,9-10H,2-3,5-7,13H2,1H3,(H,14,15)/t9-,10-,12-/m1/s1
iupac name: 2-[(1R,5S,6S)-6-(aminomethyl)-3-ethyl-6-bicyclo[3.2.0]hept-3-enyl]acetic acid
synonym: DS-5565
approved: f
ligand name: mirogabalin
type: SyntheticOrganicLigand

compound 1 [Xiao et al. 2014]
in ch i key: MTMKFBZYRGNPDF-UHFFFAOYSA-N
iupac name: [2-(2,4-dichlorophenyl)-1-methylsulfonylindol-3-yl]methanamine
synonym: indole sufonamide 1
approved: f
ligand name: compound 1 [Xiao et al. 2014]
type: SyntheticOrganicLigand

example 373 [WO2012093101]
in ch i key: SOCAXRLFGRNEPK-IFZYUDKTSA-N
comment: Example 373 from patent WO2012093101 <Reference id=27420/>, is an exemplar small molecule complement factor D inhibitor, with potential to treat age-related macular degneration (AMD). Other preferred examples are highlighted in <Reference id=27421/>.
iupac name: (1R,3S,5R)-2-N-[1-carbamoyl-5-(cyanomethoxy)indol-3-yl]-3-N-[(3-chloro-2-fluorophenyl)methyl]-2-azabicyclo[3.1.0]hexane-2,3-dicarboxamide
xref: CHEMBL2180765
approved: f
ligand name: example 373 [WO2012093101]
type: SyntheticOrganicLigand

PF-06454589
canonical SMILES: Cn1ncc(c1)c1c[nH]c2c1c(ncn2)N1CCOCC1
isomeric SMILES: Cn1ncc(c1)c1c[nH]c2c1c(ncn2)N1CCOCC1
in ch i key: VNWKCLDQBNSJJO-UHFFFAOYSA-N
in ch i: InChI=1S/C14H16N6O/c1-19-8-10(6-18-19)11-7-15-13-12(11)14(17-9-16-13)20-2-4-21-5-3-20/h6-9H,2-5H2,1H3,(H,15,16,17)
iupac name: 4-[5-(1-methylpyrazol-4-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]morpholine
synonym: compound 28 [PMID: 25353650]
approved: f
ligand name: PF-06454589
type: SyntheticOrganicLigand

tepotinib
in ch i key: AHYMHWXQRWRBKT-UHFFFAOYSA-N
in ch i: InChI=1S/C29H28N6O2/c1-34-12-10-21(11-13-34)20-37-26-17-31-29(32-18-26)25-7-3-5-23(15-25)19-35-28(36)9-8-27(33-35)24-6-2-4-22(14-24)16-30/h2-9,14-15,17-18,21H,10-13,19-20H2,1H3
comment: Tepotinib is a potent and selective, orally available inhibitor of MET tyrosine kinase <Reference id=30156/>. It was designed to inhibit the pro-oncogenic signalling caused by MET gene alterations that occur in 3-5% of NSCLC cases, and which correlate with poor prognosis. Novel tepotinib derivatives are being assessed for antiproliferative activity <Reference id=38276/>.
iupac name: 3-[1-[[3-[5-[(1-methylpiperidin-4-yl)methoxy]pyrimidin-2-yl]phenyl]methyl]-6-oxopyridazin-3-yl]benzonitrile
synonym: compound 22 [PMID: 25736998]
synonym: EMD 1214063
synonym: MSC2156119
synonym: EMD1214063
synonym: EMD-1214063
synonym: MSC2156119J
synonym: Tepmetko®
approved: t
ligand name: tepotinib
type: SyntheticOrganicLigand

AM7
in ch i key: PEGWVOKOYYAQEV-UHFFFAOYSA-N
in ch i: InChI=1S/C35H35FN4O5/c1-39-34(19-24-7-4-3-5-8-24)38-23-27(35(39)41)25-9-10-31(28(36)20-25)45-30-11-12-37-29-22-33(32(42-2)21-26(29)30)44-16-6-13-40-14-17-43-18-15-40/h3-5,7-12,20-23H,6,13-19H2,1-2H3
iupac name: 5-[3-fluoro-4-[6-methoxy-7-(3-morpholin-4-ylpropoxy)quinolin-4-yl]oxyphenyl]-3-methyl-2-(phenylmethyl)pyrimidin-4-one
xref: CHEMBL505896
synonym: pyrimidone, 22
synonym: AM 7
synonym: AM-7
approved: f
ligand name: AM7
type: SyntheticOrganicLigand

safinamide
canonical SMILES: NC(=O)C(NCc1ccc(cc1)OCc1cccc(c1)F)C
in ch i key: NEMGRZFTLSKBAP-LBPRGKRZSA-N
in ch i: InChI=1S/C17H19FN2O2/c1-12(17(19)21)20-10-13-5-7-16(8-6-13)22-11-14-3-2-4-15(18)9-14/h2-9,12,20H,10-11H2,1H3,(H2,19,21)/t12-/m0/s1
comment: Safinamide is an alpha-aminoamide. The clinically administered formulation may be the mesylate salt (PubChem CID 3038502).
xref: CHEMBL396778
synonym: EMD-1195686
synonym: EMD 1195686
synonym: Xadago®
approved: t
ligand name: safinamide
type: SyntheticOrganicLigand

entrectinib
in ch i key: HAYYBYPASCDWEQ-UHFFFAOYSA-N
in ch i: InChI=1S/C31H34F2N6O2/c1-38-8-10-39(11-9-38)25-3-4-26(29(19-25)34-24-6-12-41-13-7-24)31(40)35-30-27-17-20(2-5-28(27)36-37-30)14-21-15-22(32)18-23(33)16-21/h2-5,15-19,24,34H,6-14H2,1H3,(H2,35,36,37,40)
comment: Entrectinib is an oral, brain penetrant, receptor tyrosine kinase (RTK) inhibitor that targets solid tumours that harbour activating alterations in NTRK1, NTRK2, NTRK3 (the Trk family RTKs), ROS1 or ALK <Reference id=30141/>. NTRK1 fusion proteins are becoming recognised as oncogenic-drivers in NSCLC <Reference id=31502/>, so the ability of the compound to target these and ALK- and ROS1-rearrangements suggests it has the potential to become a very useful oncology agent.
iupac name: N-[5-[(3,5-difluorophenyl)methyl]-1H-indazol-3-yl]-4-(4-methylpiperazin-1-yl)-2-(oxan-4-ylamino)benzamide
xref: CHEMBL1983268
synonym: RXDX-101
synonym: NMS-E628
synonym: Rozlytrek®
approved: t
ligand name: entrectinib
type: SyntheticOrganicLigand

AAE-M-PBP-amine
canonical SMILES: CC(=O)NCCN(c1cccc(c1)OCCCCc1ccccc1)C
isomeric SMILES: CC(=O)NCCN(c1cccc(c1)OCCCCc1ccccc1)C
in ch i key: VJIVACBGAAEDPS-UHFFFAOYSA-N
in ch i: InChI=1S/C21H28N2O2/c1-18(24)22-14-15-23(2)20-12-8-13-21(17-20)25-16-7-6-11-19-9-4-3-5-10-19/h3-5,8-10,12-13,17H,6-7,11,14-16H2,1-2H3,(H,22,24)
xref: CHEMBL3260987
synonym: acetylaminoethyl-methyl-phenylbutoxyphenyl-amine
approved: f
ligand name: AAE-M-PBP-amine
type: SyntheticOrganicLigand

cmp5 [PMID: 25742700]
canonical SMILES: CCn1c2ccc(cc2c2c1cccc2)CNCc1cccnc1
isomeric SMILES: CCn1c2ccc(cc2c2c1cccc2)CNCc1cccnc1
in ch i key: GAVUWQFIRGBDHN-UHFFFAOYSA-N
in ch i: InChI=1S/C21H21N3/c1-2-24-20-8-4-3-7-18(20)19-12-16(9-10-21(19)24)13-23-15-17-6-5-11-22-14-17/h3-12,14,23H,2,13,15H2,1H3
comment: cmp5 is reported as a novel, first-in-class, selective small molecule inhibitor of PRMT5 <Reference id=27403/>, an arginine methyltransferase (RMT) of the histone methyltransferase (HMT) family.
iupac name: 1-(9-ethylcarbazol-3-yl)-N-(pyridin-3-ylmethyl)methanamine
synonym: ChemBridge ID 9033823
approved: f
ligand name: cmp5 [PMID: 25742700]
type: SyntheticOrganicLigand

EPZ015666
in ch i key: ZKXZLIFRWWKZRY-KRWDZBQOSA-N
in ch i: InChI=1S/C20H25N5O3/c26-17(10-25-6-5-14-3-1-2-4-15(14)9-25)8-21-20(27)18-7-19(23-13-22-18)24-16-11-28-12-16/h1-4,7,13,16-17,26H,5-6,8-12H2,(H,21,27)(H,22,23,24)/t17-/m0/s1
comment: EPZ015666 is a first-in-class, potent, selective and orally bioavailable PRMT5 inhibitor. The pharmaceutical composition may comprise the hydrochloride salt. EPZ015666 is compound 166 in patent WO2014100719 <Reference id=27406/>.
iupac name: N-[(2S)-3-(3,4-dihydro-1H-isoquinolin-2-yl)-2-hydroxypropyl]-6-(oxetan-3-ylamino)pyrimidine-4-carboxamide
synonym: EPZ-015666
synonym: EPZ 015666
approved: f
ligand name: EPZ015666
type: SyntheticOrganicLigand

tramadol
canonical SMILES: COc1cccc(c1)C1(O)CCCCC1CN(C)C
isomeric SMILES: COc1cccc(c1)C1(O)CCCCC1CN(C)C
in ch i key: TVYLLZQTGLZFBW-UHFFFAOYSA-N
in ch i: InChI=1S/C16H25NO2/c1-17(2)12-14-7-4-5-10-16(14,18)13-8-6-9-15(11-13)19-3/h6,8-9,11,14,18H,4-5,7,10,12H2,1-3H3
comment: Tramadol is a narcotic-like analgesic. The marketed formulation of tramadol is a racemic mixture of enantiomers, including PubChem CIDs 33741 and 667511 (and others). We represent the non-isomeric molecule to represent the mixture. The clinically administered form is tramadol hydrochloride.
iupac name: 2-(dimethylaminomethyl)-1-(3-methoxyphenyl)cyclohexan-1-ol
xref: CHEMBL1237044
synonym: (1RS,2RS)-2-[(dimethylamino)methyl]-1-(3-methoxyphenyl)-cyclo-hexanol
synonym: Tramacet®
synonym: Maxitram®
synonym: Tilodol®
approved: t
ligand name: tramadol
type: SyntheticOrganicLigand

S(+)-apomorphine
canonical SMILES: CN1CCc2c3C1Cc1ccc(c(c1c3ccc2)O)O
isomeric SMILES: CN1CCc2c3[C@@H]1Cc1ccc(c(c1c3ccc2)O)O
in ch i key: VMWNQDUVQKEIOC-ZDUSSCGKSA-N
in ch i: InChI=1S/C17H17NO2/c1-18-8-7-10-3-2-4-12-15(10)13(18)9-11-5-6-14(19)17(20)16(11)12/h2-6,13,19-20H,7-9H2,1H3/t13-/m0/s1
comment: S(+)-apomorphine a brain-penetrating activator of the activator of the nuclear erythroid 2-related-factor 2 (Nrf2)-ARE (antioxidant response element) pathway <Reference id=27381/>. This compound is a receptor-inactive enantiomer of the clinically approved dopamine-receptor agonist <Ligand id=33/> (R(-)-apomorphine).
iupac name: (6aS)-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline-10,11-diol
xref: CHEMBL416288
synonym: S-(+)-apomorphine
synonym: S-apomorphine
approved: f
ligand name: S(+)-apomorphine
type: SyntheticOrganicLigand

CPP-115
canonical SMILES: OC(=O)C1CC(=C(F)F)C(C1)N
isomeric SMILES: OC(=O)[C@H]1CC(=C(F)F)[C@H](C1)N
in ch i key: CBSRETZPFOBWNG-UCORVYFPSA-N
in ch i: InChI=1S/C7H9F2NO2/c8-6(9)4-1-3(7(11)12)2-5(4)10/h3,5H,1-2,10H2,(H,11,12)/t3-,5-/m0/s1
comment: CPP-115 is a <Ligand id=4821/> analogue with improved tolerability compared to the parent compound <Reference id=27378/>.
iupac name: (1S,3S)-3-amino-4-(difluoromethylidene)cyclopentane-1-carboxylic acid
xref: CHEMBL146927
synonym: compound 12 [PMID 25616005]
approved: f
ligand name: CPP-115
type: SyntheticOrganicLigand

example 7 [US8664233]
in ch i key: HFGHRUCCKVYFKL-UHFFFAOYSA-N
in ch i: InChI=1S/C21H22N6O/c1-2-28-20-19-18(25-21(26-20)27-11-9-23-10-12-27)16-4-3-15(13-17(16)24-19)14-5-7-22-8-6-14/h3-8,13,23-24H,2,9-12H2,1H3
comment: This compound is a particularly preferred example in patent US8664233 <Reference id=27358/> which covers compounds for use in treating non-solid malignant hematological tumours, in particular, B cell leukemias.
iupac name: 4-ethoxy-2-piperazin-1-yl-7-pyridin-4-yl-5H-pyrimido[5,4-b]indole
approved: f
ligand name: example 7 [US8664233]
type: SyntheticOrganicLigand

unoprostone isopropyl
in ch i key: XXUPXHKCPIKWLR-JHUOEJJVSA-N
in ch i: InChI=1S/C25H44O5/c1-4-5-6-7-10-13-20(26)16-17-22-21(23(27)18-24(22)28)14-11-8-9-12-15-25(29)30-19(2)3/h8,11,19,21-24,27-28H,4-7,9-10,12-18H2,1-3H3/b11-8-/t21-,22-,23+,24-/m1/s1
comment: Note that the INN for this compound is for the carboxylic acid, whereas the compound used clinically is the isopropyl ester. Unoprostone was originally developed as an intraocular pressure-reducing agent for use in glaucoma, however use for this indication has been discontinued. The focus is now on unoprostone's ability to treat retinal disease <Reference id=27351/><Reference id=27352/>.
iupac name: propan-2-yl (Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-(3-oxodecyl)cyclopentyl]hept-5-enoate
xref: CHEMBL1200661
synonym: UF-021
synonym: UF 021
synonym: Rescula® (proposed trade name)
approved: t
ligand name: unoprostone isopropyl
type: SyntheticOrganicLigand

treosulfan
canonical SMILES: OC(C(COS(=O)(=O)C)O)COS(=O)(=O)C
isomeric SMILES: OC(C(COS(=O)(=O)C)O)COS(=O)(=O)C
in ch i key: YCPOZVAOBBQLRI-UHFFFAOYSA-N
in ch i: InChI=1S/C6H14O8S2/c1-15(9,10)13-3-5(7)6(8)4-14-16(2,11)12/h5-8H,3-4H2,1-2H3
comment: Treosulfan is a DNA alkylating agent.
iupac name: (2,3-dihydroxy-4-methylsulfonyloxybutyl) methanesulfonate
xref: CHEMBL2358556
synonym: Trecondi®
approved: t
ligand name: treosulfan
type: SyntheticOrganicLigand

tirasemtiv
canonical SMILES: CCC(n1c(=O)[nH]c2c1nc(C#C)cn2)CC
isomeric SMILES: CCC(n1c(=O)[nH]c2c1nc(C#C)cn2)CC
in ch i key: RSQGZEAXODVTOL-UHFFFAOYSA-N
in ch i: InChI=1S/C12H14N4O/c1-4-8-7-13-10-11(14-8)16(12(17)15-10)9(5-2)6-3/h1,7,9H,5-6H2,2-3H3,(H,13,15,17)
comment: Tirasemtiv acts as an activator of the fast skeletal muscle (type II) troponin complex <Reference id=27349/>. The compound is being investigated as a potential treatment for diseases and conditions associated with aging, muscle weakness and wasting or neuromuscular dysfunction <Reference id=27349/> (e.g. amyotrophic lateral sclerosis <Reference id=43189/>, myasthenia gravis and claudication <Reference id=27347/>). In clinical trial tirasemtiv was not well tolerated, and this was likely a contributory factor to its lack of significant efficacy.
iupac name: 5-ethynyl-3-pentan-3-yl-1H-imidazo[4,5-b]pyrazin-2-one
xref: CHEMBL3039529
synonym: CK-2017357
approved: f
ligand name: tirasemtiv
type: SyntheticOrganicLigand

talampanel
in ch i key: JACAAXNEHGBPOQ-LLVKDONJSA-N
in ch i: InChI=1S/C19H19N3O3/c1-11-7-14-8-17-18(25-10-24-17)9-16(14)19(21-22(11)12(2)23)13-3-5-15(20)6-4-13/h3-6,8-9,11H,7,10,20H2,1-2H3/t11-/m1/s1
comment: Talampanel is a non-competitive antagonist of the AMPA receptors, a family of ionotropic glutamate receptors of the central nervous system. The compound shows some selectivity for GluA1 and GluA2 over GluA3 and GluA4 <Reference id=27346/>.
iupac name: 1-[(8R)-5-(4-aminophenyl)-8-methyl-8,9-dihydro-[1,3]dioxolo[4,5-h][2,3]benzodiazepin-7-yl]ethanone
xref: CHEMBL61872
synonym: GYKI 537773
synonym: LY300164
synonym: LY-300164
approved: f
ligand name: talampanel
type: SyntheticOrganicLigand

plevitrexed
in ch i key: IEJSCSAMMLUINT-NRFANRHFSA-N
in ch i: InChI=1S/C26H25FN8O4/c1-4-9-35(13-16-11-19-22(10-14(16)2)28-15(3)29-25(19)37)17-5-6-18(20(27)12-17)24(36)30-21(26(38)39)7-8-23-31-33-34-32-23/h1,5-6,10-12,21H,7-9,13H2,2-3H3,(H,30,36)(H,38,39)(H,28,29,37)(H,31,32,33,34)/t21-/m0/s1
comment: Plevitrexed is an orally bioavailable, small molecule, antifolate quinazoline derivative inhibitor of thymidylate synthetase with potential antineoplastic activity <Reference id=27344/>.
iupac name: (2S)-2-[[4-[(2,7-dimethyl-4-oxo-1H-quinazolin-6-yl)methyl-prop-2-ynylamino]-2-fluorobenzoyl]amino]-4-(2H-tetrazol-5-yl)butanoic acid
xref: CHEMBL126648
synonym: ZD-9331
synonym: ZD9331
synonym: ZD 9331
approved: f
ligand name: plevitrexed
type: SyntheticOrganicLigand

palovarotene
isomeric SMILES: OC(=O)c1ccc(cc1)/C=C/c1cc2c(cc1Cn1cccn1)C(C)(C)CCC2(C)C
in ch i key: YTFHCXIPDIHOIA-DHZHZOJOSA-N
in ch i: InChI=1S/C27H30N2O2/c1-26(2)12-13-27(3,4)24-17-22(18-29-15-5-14-28-29)21(16-23(24)26)11-8-19-6-9-20(10-7-19)25(30)31/h5-11,14-17H,12-13,18H2,1-4H3,(H,30,31)/b11-8+
comment: Palovarotene is an orally bioavailable, retinoic acid receptor gamma (RAR-γ) agonist. This compound was originally investegated for its potential to repair alveolar damage in emphysema and COPD <Reference id=27336/><Reference id=27337/>, but it failed to demonstrate significant clinical efficacy. Ipsen acquired palovarotene when it purchased Clementia Pharmaceuticals in 2019, and they repurposed palovarotene for potential to reduce heterotopic ossification in patients with fibrodysplasia ossificans progressiva (FOP) <Reference id=43851/><Reference id=43852/>.
iupac name: 4-[(E)-2-[5,5,8,8-tetramethyl-3-(pyrazol-1-ylmethyl)-6,7-dihydronaphthalen-2-yl]ethenyl]benzoic acid
xref: CHEMBL2105648
synonym: R-667
synonym: Ro-3300074
synonym: Sohonos®
synonym: R667
synonym: CLM-001
synonym: IPN60120
synonym: IPN-60120
synonym: RG-667
approved: t
ligand name: palovarotene
type: SyntheticOrganicLigand

niraparib
canonical SMILES: NC(=O)c1cccc2c1nn(c2)c1ccc(cc1)C1CCCNC1
in ch i key: PCHKPVIQAHNQLW-CQSZACIVSA-N
in ch i: InChI=1S/C19H20N4O/c20-19(24)17-5-1-3-15-12-23(22-18(15)17)16-8-6-13(7-9-16)14-4-2-10-21-11-14/h1,3,5-9,12,14,21H,2,4,10-11H2,(H2,20,24)/t14-/m1/s1
comment: Niraparib is a novel orally available poly(ADP-ribose) polymerase (PARP) inhibitor <Reference id=27335/>.
iupac name: 2-[4-[(3S)-piperidin-3-yl]phenyl]indazole-7-carboxamide
xref: CHEMBL1094636
synonym: MK 4827
synonym: MK-4827
synonym: compound 56 [PMID 19873981]
synonym: Zejula®
approved: t
ligand name: niraparib
type: SyntheticOrganicLigand

mifamurtide
in ch i key: JMUHBNWAORSSBD-ZXSMYVEWSA-N
comment: Mifamurtide is a synthetic analogue of the bacterial cell wall component, muramyl dipeptide (MDP). MDP stimulates the immune system via activation of microbial pattern recognition receptors such as TLR4 and NOD2 <Reference id=27329/><Reference id=27330/>.
iupac name: [3-[2-[[(2S)-2-[[(4R)-4-[[(2S)-2-[[(2R)-2-[(2R,3R,4R,6R)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxypropanoyl]amino]propanoyl]amino]-5-amino-5-oxopentanoyl]amino]propanoyl]amino]ethoxy-hydroxyphosphoryl]oxy-2-hexadecanoyloxypropyl] hexadecanoate
synonym: L-MTP-PE
synonym: Mepact®
synonym: liposomal muramyl tripeptide phosphatidyl ethanolamine
synonym: CGP 19835
synonym: CGP-19835
synonym: MLV 19835A
approved: t
ligand name: mifamurtide
type: SyntheticOrganicLigand

imexon
canonical SMILES: NC1=NC(=O)N2C1C2
isomeric SMILES: NC1=NC(=O)N2C1C2
in ch i key: BIXBBIPTYBJTRY-UHFFFAOYSA-N
in ch i: InChI=1S/C4H5N3O/c5-3-2-1-7(2)4(8)6-3/h2H,1H2,(H2,5,6,8)
comment: Imexon is a cyclizised 2-cyanoaziridine compound being investigated as an antitumour agent <Reference id=27317/><Reference id=27322/>. 2-cyanoaziridine compounds bind thiols such as cysteine, depleting them and allowing the accumulation of reactive oxygen species. This effect activates antioxidant gene expression, signifying induction of an oxidative stress response <Reference id=27318/> and leads to irreversible cell damage and apoptosis.
iupac name: 4-amino-1,3-diazabicyclo[3.1.0]hex-3-en-2-one
xref: CHEMBL146428
synonym: BM-06002
synonym: BM 06002
synonym: Amplimexon® (proposed trade name)
approved: f
ligand name: imexon
type: SyntheticOrganicLigand

forodesine
canonical SMILES: OCC1NC(C(C1O)O)c1c[nH]c2c1[nH]cnc2=O
in ch i key: IWKXDMQDITUYRK-KUBHLMPHSA-N
in ch i: InChI=1S/C11H14N4O4/c16-2-5-9(17)10(18)7(15-5)4-1-12-8-6(4)13-3-14-11(8)19/h1,3,5,7,9-10,12,15-18H,2H2,(H,13,14,19)/t5-,7+,9-,10+/m1/s1
comment: Forodesine is a picomolar inhibitor of purine nucleoside phosphorylase (PNP) <Reference id=27315/><Reference id=27313/>. The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
iupac name: 7-[(2S,3S,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)pyrrolidin-2-yl]-1,5-dihydropyrrolo[2,3-e]pyrimidin-4-one
xref: CHEMBL218291
synonym: BCX-1777
synonym: BCX1777
synonym: Fodosine® (proposed trade name)
synonym: immucillin H
synonym: immucillin-H
approved: f
ligand name: forodesine
type: SyntheticOrganicLigand

arimoclomol
canonical SMILES: OC(CN1CCCCC1)CON=C(c1ccc[n+](c1)[O-])Cl
isomeric SMILES: O[C@H](CN1CCCCC1)CO/N=C(/c1ccc[n+](c1)[O-])/Cl
in ch i key: SGEIEGAXKLMUIZ-XUVDNFPMSA-N
in ch i: InChI=1S/C14H20ClN3O3/c15-14(12-5-4-8-18(20)9-12)16-21-11-13(19)10-17-6-2-1-3-7-17/h4-5,8-9,13,19H,1-3,6-7,10-11H2/b16-14-/t13-/m1/s1
comment: Arimoclomol is an oral therapeutic candidate for the treatment of amyotrophic lateral sclerosis (ALS). Arimoclomol may be delivered as the citrate salt (BRX-345 with PubChem CID 72710735)
iupac name: N-[(2R)-2-hydroxy-3-piperidin-1-ylpropoxy]-1-oxidopyridin-1-ium-3-carboximidoyl chloride
xref: CHEMBL2107726
synonym: BRX-220
synonym: BRX220
approved: f
ligand name: arimoclomol
type: SyntheticOrganicLigand

1-methyl-L-tryptophan
canonical SMILES: OC(=O)C(Cc1cn(c2c1cccc2)C)N
isomeric SMILES: OC(=O)[C@H](Cc1cn(c2c1cccc2)C)N
in ch i key: ZADWXFSZEAPBJS-JTQLQIEISA-N
in ch i: InChI=1S/C12H14N2O2/c1-14-7-8(6-10(13)12(15)16)9-4-2-3-5-11(9)14/h2-5,7,10H,6,13H2,1H3,(H,15,16)/t10-/m0/s1
comment: 1-methyl-L-tryptophan was identified as an inhibitor of indoleamine 2,3-dioxygenase 1 (IDO1) in the 1990s, but it has a very low potency <Reference id=27057/><Reference id=27058/>.
iupac name: (2S)-2-amino-3-(1-methylindol-3-yl)propanoic acid
xref: CHEMBL504816
synonym: 1-L-MT
synonym: 1-LMT
approved: f
ligand name: 1-methyl-L-tryptophan
type: SyntheticOrganicLigand

pr1 nanopeptide
in ch i key: WOACUGNMTZAEJZ-GXLXRQKGSA-N
in ch i: InChI=1S/C45H79N11O15/c1-19(2)16-27(40(65)52-29(18-31(47)59)41(66)54-34(22(7)8)43(68)56-36(24(11)57)44(69)55-35(23(9)10)45(70)71)51-38(63)26(13-15-32(60)61)49-37(62)25(12-14-30(46)58)50-39(64)28(17-20(3)4)53-42(67)33(48)21(5)6/h19-29,33-36,57H,12-18,48H2,1-11H3,(H2,46,58)(H2,47,59)(H,49,62)(H,50,64)(H,51,63)(H,52,65)(H,53,67)(H,54,66)(H,55,69)(H,56,68)(H,60,61)(H,70,71)/t24-,25+,26+,27+,28+,29+,33+,34+,35+,36+/m1/s1
comment: PR1 nanopeptide is is a nonapeptide sequence found in human proteinase 3 (PRTN3) and ELA2 which is expressed as a leukemia-associated antigen <Reference id=27276/>. PR1 nanopeptide elicits potent binding to HLA-A2.1.
approved: f
ligand name: pr1 nanopeptide
type: PeptideLigand

compound 6e [PMID: 25614116 ]
in ch i key: PQYQQIZSHUQNNZ-UHFFFAOYSA-N
in ch i: InChI=1S/C26H24O7/c1-17(27)21-11-10-20(30-15-19-8-5-9-23-26(19)32-16-31-23)14-24(21)33-22(12-13-25(28)29)18-6-3-2-4-7-18/h2-11,14,22H,12-13,15-16H2,1H3,(H,28,29)
comment: Compound 6e is potent and selective endothelin receptor (ETA) antagonist. It has therapeutic potential in cardiovascular diseases <Reference id=27275/>.
iupac name: 4-[2-acetyl-5-(2H-1,3-benzodioxol-4-ylmethoxy)phenoxy]-4-phenylbutanoic acid
approved: f
ligand name: compound 6e [PMID: 25614116 ]
type: SyntheticOrganicLigand

(S)-DRF-1042
in ch i key: UPAYPYZHFCRCMO-UNMCSNQZSA-N
in ch i: InChI=1S/C22H20N2O6/c1-2-22(28)11-13-10-16-17-14(9-12-5-3-4-6-15(12)23-17)20(29-8-7-25)24(16)19(26)18(13)30-21(22)27/h3-6,9-10,20,25,28H,2,7-8,11H2,1H3/t20-,22-/m0/s1
comment: S-isomer of DRF-1042 is a derivative of camptothecin, a natural quinoline alkaloid with cytotoxic effects, which acts to inhibit DNA topoisomerase I. This compound only contains the (S) stereoisomer, as described in patent US20110177161 <Reference id=27274/>. PubChem CID 23631031 represents the molecule with no specified stereochemistry at the 5 position. Two camptothecin derivatives are already approved for clinical use: <Ligand id=7101/> and <Ligand id=6823/>.
synonym: 5(S)-(2'-hydroxyethoxy)-20(S)-camptothecin
synonym: 5(S)-(2'-hydroxyethoxy)-20(S)-CPT
approved: f
ligand name: (S)-DRF-1042
type: SyntheticOrganicLigand

avosentan
in ch i key: YBWLTKFZAOSWSM-UHFFFAOYSA-N
in ch i: InChI=1S/C23H21N5O5S/c1-15-8-9-19(25-14-15)34(29,30)28-22-20(33-18-7-5-4-6-17(18)31-2)23(32-3)27-21(26-22)16-10-12-24-13-11-16/h4-14H,1-3H3,(H,26,27,28)
comment: Avosentan is an endothelin A antagonist indicated for diabetic nephropathy. Speedel licensed SPP301 from Hoffmann-La Roche in 2000.
iupac name: N-[6-methoxy-5-(2-methoxyphenoxy)-2-pyridin-4-ylpyrimidin-4-yl]-5-methylpyridine-2-sulfonamide
synonym: SPP-301
synonym: Ro 67-0565
approved: f
ligand name: avosentan
type: SyntheticOrganicLigand

CM-352
in ch i key: ZUZGJCNWNOCKEB-XMMPIXPASA-N
in ch i: InChI=1S/C24H29N3O6S/c1-25-21(28)17-2-4-18(5-3-17)33-19-6-8-20(9-7-19)34(31,32)24(22(29)27-30)11-10-23(16-24)12-14-26-15-13-23/h2-9,26,30H,10-16H2,1H3,(H,25,28)(H,27,29)/t24-/m1/s1
comment: CM-352 is an optimized matrix metalloproteinase (MMP) inhibitor which inhibits fibrinolysis, and represents a novel type of antihaemorrhagic agent <Reference id=27268/>. PubChem CID 72720906 represents the molecule without the stereochemistry attributed in <Reference id=27268/>.
synonym: compound 2 [PMID 25686022]
approved: f
ligand name: CM-352
type: SyntheticOrganicLigand

CPHPC
in ch i key: HZLAWYIBLZNRFZ-VXGBXAGGSA-N
in ch i: InChI=1S/C16H24N2O6/c19-13(17-9-3-5-11(17)15(21)22)7-1-2-8-14(20)18-10-4-6-12(18)16(23)24/h11-12H,1-10H2,(H,21,22)(H,23,24)/t11-,12-/m1/s1
comment: CPHPC is reported as a chemical which depletes the glycoprotein serum amyloid P component (SAP) in mice <Reference id=27225/> and humans <Reference id=27227/>. Intellectual property for the use of CPHPC has been licensed to GlaxoSmithKline who have coded the compound GSK2315698. Structurally, CPHPC is a simplified form of a <Ligand id=5158/> dimer <Reference id=27226/>.
iupac name: (2R)-1-[6-[(2R)-2-carboxypyrrolidin-1-yl]-6-oxohexanoyl]pyrrolidine-2-carboxylic acid
xref: CHEMBL25263
synonym: GSK2315698
synonym: compound 52 [PMID 14998318]
synonym: Ro 63-8695
approved: f
ligand name: CPHPC
type: SyntheticOrganicLigand

sotuletinib
in ch i key: ADZBMFGQQWPHMJ-RHSMWYFYSA-N
in ch i: InChI=1S/C20H22N4O3S/c1-21-19(26)16-10-13(8-9-22-16)27-12-6-7-15-18(11-12)28-20(24-15)23-14-4-2-3-5-17(14)25/h6-11,14,17,25H,2-5H2,1H3,(H,21,26)(H,23,24)/t14-,17-/m1/s1
comment: BLZ945 is reported as an orally active, potent and selective inhibitor of colony stimulating factor 1 receptor (CSF1R) <Reference id=27189/>. It is also brain-penetrant. The compound was designed to deplete pro-tumorigenic tumour-associated macrophages (TAMs) in the tumour microenvironment <Reference id=27189/>, and has also been reported to inhibit osteoclast CSF1R activity which reduces skeletal related events in metastatic disease <Reference id=27190/>. The chemical structure of BLZ945 matches that for the INN compound sotuletinib that was surfaced in WHO Proposed list 125.
iupac name: 4-[[2-[[(1R,2R)-2-hydroxycyclohexyl]amino]-1,3-benzothiazol-6-yl]oxy]-N-methylpyridine-2-carboxamide
synonym: BLZ 945
synonym: BLZ-945
synonym: BLZ945
approved: f
ligand name: sotuletinib
type: SyntheticOrganicLigand

bromosporine
in ch i key: UYBRROMMFMPJAN-UHFFFAOYSA-N
in ch i: InChI=1S/C17H20N6O4S/c1-5-27-17(24)18-15-9-14(21-23-11(3)19-20-16(15)23)12-7-6-10(2)13(8-12)22-28(4,25)26/h6-9,22H,5H2,1-4H3,(H,18,24)
comment: Bromosporine is a broad spectrum inhibitor of bromodomain-containing proteins. This is contained in the Structural Genomics Consortium's (SGC) Epigenetics Probes Collection.
iupac name: ethyl N-[6-(3-methanesulfonamido-4-methylphenyl)-3-methyl-[1,2,4]triazolo[4,3-b]pyridazin-8-yl]carbamate
xref: CHEMBL3133807
approved: f
ligand name: bromosporine
type: SyntheticOrganicLigand

RN486
in ch i key: ZTUJNJAKTLHBEX-UHFFFAOYSA-N
in ch i: InChI=1S/C35H35FN6O3/c1-39-12-14-41(15-13-39)26-8-9-32(37-19-26)38-30-18-25(20-40(2)34(30)44)27-4-3-5-31(28(27)21-43)42-11-10-23-16-24(22-6-7-22)17-29(36)33(23)35(42)45/h3-5,8-11,16-20,22,43H,6-7,12-15,21H2,1-2H3,(H,37,38)
comment: RN486 is reported as a reversible, potent and selective inhibitor of Bruton agammaglobulinemia tyrosine kinase (BTK) <Reference id=26756/><Reference id=27188/>.
iupac name: 6-cyclopropyl-8-fluoro-2-[2-(hydroxymethyl)-3-[1-methyl-5-[[5-(4-methylpiperazin-1-yl)pyridin-2-yl]amino]-6-oxopyridin-3-yl]phenyl]isoquinolin-1-one
xref: CHEMBL2057918
synonym: RN-486
synonym: compound 29 [PMID 22394077]
approved: f
ligand name: RN486
type: SyntheticOrganicLigand

LY2584702
in ch i key: FYXRSVDHGLUMHB-UHFFFAOYSA-N
in ch i: InChI=1S/C21H19F4N7/c1-31-10-17(13-2-3-16(22)15(8-13)21(23,24)25)29-19(31)12-4-6-32(7-5-12)20-14-9-28-30-18(14)26-11-27-20/h2-3,8-12H,4-7H2,1H3,(H,26,27,28,30)
comment: LY2584702 is reported as an ATP competitive, selective inhibitor of the p70 ribosomal protein S6 kinase (p70S6K) <Reference id=27186/>. p70S6K is a downstream component of the PI3K/Akt/mTOR signalling pathway which regulates cell proliferation and survival. LY2584702 was originally developed as a potential oncology therapeutic, but the programme was terminated due to a lack of clinical efficacy. Subsequent study has discovered that LY2584702 produces effects that indicate potential efficacy as a therapy for dyslipidemia <Reference id=35002/>. In healthy dyslipidemic volunteers LY2584702 dose‐dependently and significantly reduced pasma low‐density lipoprotein cholesterol and triglycerides, whilst leaving high‐density lipoprotein cholesterol levels unchanged. However, metabolism of LY2584702 generates 4-aminopyrazolo[3,4-d]pyrimidine (4-APP; PubChem CID 75420), a compound which may contribute towards the adverse hepatotoxicity associated with LY2584702 exposure. Further determination of the anti-dyslipidemia potential of p70S6K inhibitors could be advanced by the development of non-4-APP forming compounds.
iupac name: 4-[4-[4-[4-fluoro-3-(trifluoromethyl)phenyl]-1-methylimidazol-2-yl]piperidin-1-yl]-1H-pyrazolo[3,4-d]pyrimidine
synonym: LY 2584702
synonym: LY-2584702
approved: f
ligand name: LY2584702
type: SyntheticOrganicLigand

LDC1267
in ch i key: ISPBCAXOSOLFME-UHFFFAOYSA-N
in ch i: InChI=1S/C30H26F2N4O5/c1-5-40-28-16-36(23-8-6-18(31)12-17(23)2)35-29(28)30(37)34-19-7-9-25(21(32)13-19)41-24-10-11-33-22-15-27(39-4)26(38-3)14-20(22)24/h6-16H,5H2,1-4H3,(H,34,37)
comment: LDC1267 is a selective inhibitor of TAM family kinases (Type XI receptor tyrosine kinases, TYRO3, Axl and MER) <Reference id=27185/>.
iupac name: N-[4-(6,7-dimethoxyquinolin-4-yl)oxy-3-fluorophenyl]-4-ethoxy-1-(4-fluoro-2-methylphenyl)pyrazole-3-carboxamide
approved: f
ligand name: LDC1267
type: SyntheticOrganicLigand

SD-208
in ch i key: BERLXWPRSBJFHO-UHFFFAOYSA-N
in ch i: InChI=1S/C17H10ClFN6/c18-10-1-2-13(19)12(9-10)15-24-16-14(21-7-8-22-16)17(25-15)23-11-3-5-20-6-4-11/h1-9H,(H,20,22,23,24,25)
comment: SD-208 is a selective, ATP-competitive inhibitor of TGFβR1 (ALK5) <Reference id=27183/>. SD-208 is compound 14 in patent WO2005032481 <Reference id=27184/>.
iupac name: 2-(5-chloro-2-fluorophenyl)-N-pyridin-4-ylpteridin-4-amine
xref: CHEMBL238125
synonym: SCI-208
synonym: SD 208
approved: f
ligand name: SD-208
type: SyntheticOrganicLigand

ZM-306416
canonical SMILES: COc1cc2c(ncnc2cc1OC)Nc1ccc(cc1F)Cl
isomeric SMILES: COc1cc2c(ncnc2cc1OC)Nc1ccc(cc1F)Cl
in ch i key: YHUIUSRCUKUUQA-UHFFFAOYSA-N
comment: ZM-306416 is reported as an inhibitor of VEGFR and EGFR <Reference id=27181/>. Hennequin et al (1999) report selectivity for VEGFR2 (KDR) over VEGFR1 (Flt-1) <Reference id=27182/> (ZM-306416 is compound 4 in <Reference id=27182/>).
iupac name: N-(4-chloro-2-fluorophenyl)-6,7-dimethoxyquinazolin-4-amine
xref: CHEMBL150315
synonym: CB-676475
synonym: ZM306416
synonym: ZM 306416
approved: f
ligand name: ZM-306416
type: SyntheticOrganicLigand

TGX-221
in ch i key: CPRAGQJXBLMUEL-UHFFFAOYSA-N
in ch i: InChI=1S/C21H24N4O2/c1-15-12-18(16(2)22-17-6-4-3-5-7-17)21-23-19(13-20(26)25(21)14-15)24-8-10-27-11-9-24/h3-7,12-14,16,22H,8-11H2,1-2H3
comment: TGX-221 is reported as a selective inhibitor of phosphatidylinositol 3-kinase (PI3K) β <Reference id=27180/>.
iupac name: 7-methyl-2-morpholin-4-yl-9-[1-(phenylamino)ethyl]pyrido[2,1-b]pyrimidin-4-one
xref: CHEMBL1972466
synonym: TGX 221
approved: f
ligand name: TGX-221
type: SyntheticOrganicLigand

HS-173
in ch i key: SEKOTFCHZNXZMM-UHFFFAOYSA-N
in ch i: InChI=1S/C21H18N4O4S/c1-2-29-21(26)19-13-23-20-9-8-15(14-25(19)20)16-10-17(12-22-11-16)24-30(27,28)18-6-4-3-5-7-18/h3-14,24H,2H2,1H3
comment: HS-173 (as compound 19c) is reported as a selective inhibitor of phosphatidylinositol 3-kinase (PI3K) α <Reference id=27177/>.
iupac name: ethyl 6-[5-(benzenesulfonamido)pyridin-3-yl]imidazo[1,2-a]pyridine-3-carboxylate
xref: CHEMBL1765463
approved: f
ligand name: HS-173
type: SyntheticOrganicLigand

PI-3065
in ch i key: YDNOHCOYQVZOMC-UHFFFAOYSA-N
in ch i: InChI=1S/C27H31FN6OS/c28-21-3-4-22-20(5-6-29-22)24(21)26-30-23-15-19(17-33-9-7-32(8-10-33)16-18-1-2-18)36-25(23)27(31-26)34-11-13-35-14-12-34/h3-6,15,18,29H,1-2,7-14,16-17H2
comment: PI-3065 is reported as a selective inhibitor of phosphatidylinositol 3-kinase (PI3K) δ <Reference id=27176/>. The compound is >70 fold selective for PI3Kδ compared to PI3Kβ, and has even higher selectivity compared to the δ and α isoforms. In a profile screening set of 72 kinases no significant off-targets were identified <Reference id=27176/>.
iupac name: 4-[6-[[4-(cyclopropylmethyl)piperazin-1-yl]methyl]-2-(5-fluoro-1H-indol-4-yl)thieno[3,2-d]pyrimidin-4-yl]morpholine
synonym: PI 3065
approved: f
ligand name: PI-3065
type: SyntheticOrganicLigand

GSK-LSD1
canonical SMILES: N1CCC(CC1)NC1CC1c1ccccc1
isomeric SMILES: N1CCC(CC1)N[C@@H]1C[C@H]1c1ccccc1
in ch i key: BASFYRLYJAZPPL-UONOGXRCSA-N
in ch i: InChI=1S/C14H20N2/c1-2-4-11(5-3-1)13-10-14(13)16-12-6-8-15-9-7-12/h1-5,12-16H,6-10H2/t13-,14+/m0/s1
comment: GSK-LSD1 is a potent, selective and irreversible inhibitor of lysine specific demethylase 1 (LSD1; gene symbol KDM1A) <Reference id=27143/>. The compound was developed by GlaxoSmithKline and has been made available for inclusion in the portfolio of compounds held by the Structural Genomics Consortium (SGC) in their Epigenetics Probes Collection.
iupac name: N-[(1R,2S)-2-phenylcyclopropyl]piperidin-4-amine
approved: f
ligand name: GSK-LSD1
type: SyntheticOrganicLigand

GSK343
in ch i key: ULNXAWLQFZMIHX-UHFFFAOYSA-N
in ch i: InChI=1S/C31H39N7O2/c1-6-7-23-14-21(4)35-31(40)26(23)18-33-30(39)25-15-24(16-28-27(25)19-34-38(28)20(2)3)22-8-9-32-29(17-22)37-12-10-36(5)11-13-37/h8-9,14-17,19-20H,6-7,10-13,18H2,1-5H3,(H,33,39)(H,35,40)
comment: GSK343 is a cell-permeable inhibitor of EZH2 histone H3 methyltransferase activity, developed by GlaxoSmithKline and included in the Structural Genomics Consortium's (SGCs) portfilio of epigenetic probe compounds <Reference id=27141/><Reference id=27142/>. Click here to link to the SGC's full list of epigenetics probes.
iupac name: N-[(6-methyl-2-oxo-4-propyl-1,2-dihydropyridin-3-yl)methyl]-6-[2-(4-methylpiperazin-1-yl)pyridin-4-yl]-1-(propan-2-yl)-1H-indazole-4-carboxamide
xref: CHEMBL2204995
synonym: compound 6 [PMID 24900432]
synonym: GSK 343
approved: f
ligand name: GSK343
type: SyntheticOrganicLigand

LLY-507
in ch i key: PNYRDVBFYVDJJI-UHFFFAOYSA-N
in ch i: InChI=1S/C36H42N6O/c1-28-27-42(34-11-4-2-9-32(28)34)22-19-40-17-20-41(21-18-40)35-12-5-3-10-33(35)30-23-29(26-37)24-31(25-30)36(43)38-13-8-16-39-14-6-7-15-39/h2-5,9-12,23-25,27H,6-8,13-22H2,1H3,(H,38,43)
comment: LLY-507 is a potent inhibitor of SMYD2 protein lysine methyltransferase activity, developed in a collaboration between the Structural Genomics Consortium (SGC) and Eli Lilly and Company <Reference id=27140/>. Click here to link to the SGC's full list of epigenetics probes.
iupac name: 3-cyano-5-(2-{4-[2-(3-methyl-1H-indol-1-yl)ethyl]piperazin-1-yl}phenyl)-N-[3-(pyrrolidin-1-yl)propyl]benzamide
approved: f
ligand name: LLY-507
type: SyntheticOrganicLigand

A-366
canonical SMILES: COc1cc2c(cc1OCCCN1CCCC1)N=C(C12CCC1)N
isomeric SMILES: COc1cc2c(cc1OCCCN1CCCC1)N=C(C12CCC1)N
in ch i key: BKCDJTRMYWSXMC-UHFFFAOYSA-N
in ch i: InChI=1S/C19H27N3O2/c1-23-16-12-14-15(21-18(20)19(14)6-4-7-19)13-17(16)24-11-5-10-22-8-2-3-9-22/h12-13H,2-11H2,1H3,(H2,20,21)
comment: A-366 is a chemical probe for the activity of the histone methyltransferases (HMTs) EHMT2 (G9a) and EHMT1 (GLP), developed by the Structural Genomics Consortium (SGC) in collaboration with Abbvie <Reference id=27138/><Reference id=27139/>. Click here to link to the SGC's full list of epigenetics probes.
iupac name: 5'-methoxy-6'-[3-(pyrrolidin-1-yl)propoxy]spiro[cyclobutane-1,3'-indole]-2'-amine
xref: CHEMBL3109630
synonym: A 366
synonym: A366
approved: f
ligand name: A-366
type: SyntheticOrganicLigand

UNC1999
in ch i key: DPJNKUOXBZSZAI-UHFFFAOYSA-N
in ch i: InChI=1S/C33H43N7O2/c1-7-8-24-15-23(6)37-33(42)28(24)19-35-32(41)27-16-26(17-30-29(27)20-36-40(30)22(4)5)25-9-10-31(34-18-25)39-13-11-38(12-14-39)21(2)3/h9-10,15-18,20-22H,7-8,11-14,19H2,1-6H3,(H,35,41)(H,37,42)
comment: UNC1999 is a cell-permeable chemical probe for histone H3-lysine 27 (H3K27) methyltransferase EZH2 activity, developed by the Structural Genomics Consortium (SGC) in collaboration with the Center for Integrative Chemical Biology and Drug Discovery (CICBDD) at the University of North Carolina <Reference id=27133/><Reference id=27132/>. Click here to link to the SGC's full list of epigenetics probes.
iupac name: N-[(6-methyl-2-oxo-4-propyl-1,2-dihydropyridin-3-yl)methyl]-1-(propan-2-yl)-6-{6-[4-(propan-2-yl)piperazin-1-yl]pyridin-3-yl}-1H-indazole-4-carboxamide
synonym: UNC 1999
synonym: UNC-1999
approved: f
ligand name: UNC1999
type: SyntheticOrganicLigand

I-CBP112
in ch i key: YKNAKDFZAWQEEO-IBGZPJMESA-N
in ch i: InChI=1S/C27H36N2O5/c1-5-26(30)29-11-12-33-27-22(17-29)13-21(20-8-9-23(31-3)24(14-20)32-4)15-25(27)34-18-19-7-6-10-28(2)16-19/h8-9,13-15,19H,5-7,10-12,16-18H2,1-4H3/t19-/m0/s1
comment: I-CBP112 is an inhibitor of the bromodomain-containing proteins CREB binding protein (CREBBP) and E1A binding protein p300 (EP300) and was developed by the Structural Genomics Consortium (SGC) <Reference id=27128/>. The bromodomains facilitate binding of these proteins to acetylated lysine residues on histones and other proteins <Reference id=27129/>, interactions which underlie the function of these two transctiptional co-activators in the control of DNA replication and repair, cell growth, transformation, and development <Reference id=27130/><Reference id=27131/>. Click here to link to the SGC's full list of epigenetics probes.
iupac name: 1-[7-(3,4-dimethoxyphenyl)-9-{[(3S)-1-methylpiperidin-3-yl]methoxy}-2,3,4,5-tetrahydro-1,4-benzoxazepin-4-yl]propan-1-one
approved: f
ligand name: I-CBP112
type: SyntheticOrganicLigand

(R)-PFI-2
in ch i key: JCKGSPAAPQRPBW-OAQYLSRUSA-N
comment: (R)-PFI-2 is a first-in-class, potent, selective, and cell-permeable inhibitor of the methyltransferase activity of human SETD7 <Reference id=27127/>. The S-enantiomer is 500-fold less potent. (R)-PFI-2 can be used as a chemical probe to resolve the diverse roles of SETD7 in cellular function, and may provide insight for the potential of methyltransferases as valid drug targets. This is a compound from the Structural Genomics Consortium's (SGC) Epigenetics Probes Collection.
iupac name: 8-fluoro-N-[(2R)-1-oxo-1-pyrrolidin-1-yl-3-[3-(trifluoromethyl)phenyl]propan-2-yl]-1,2,3,4-tetrahydroisoquinoline-6-sulfonamide
approved: f
ligand name: (R)-PFI-2
type: SyntheticOrganicLigand

GSK2801
in ch i key: KHWCPNJRJCNVRI-UHFFFAOYSA-N
in ch i: InChI=1S/C20H21NO4S/c1-4-11-25-15-9-10-21-18(14(2)22)13-17(19(21)12-15)16-7-5-6-8-20(16)26(3,23)24/h5-10,12-13H,4,11H2,1-3H3
comment: GSK2801 is reported by the Structural Genomics Consortium (SGC) to be a selective inhibitor of the ubiquitously expressed bromodomain containing proteins BAZ2A and BAZ2B <Reference id=27123/>. BAZ2A is essential for heterochromatin formation leading to transcriptional silencing of certain rRNAs <Reference id=27125/>. BAZ2B may be involved in regulating nucleosome mobilization by the ATP-dependent chromatin remodeling factor ISWI <Reference id=27124/>. Click here to link to the SGC's full list of epigenetics probes.
iupac name: 1-(7-(2-methylsulfonyl-phenyl)-4-propoxy-1-aza-bicyclo[4.3.0]nona-2,4,6,8-tetraen-9-yl)-ethanone
synonym: KB-146016
approved: f
ligand name: GSK2801
type: SyntheticOrganicLigand

UNC1215
in ch i key: PQOOIERVZAXHBP-UHFFFAOYSA-N
in ch i: InChI=1S/C32H43N5O2/c38-31(36-20-12-27(13-21-36)34-16-4-5-17-34)25-10-11-29(30(24-25)33-26-8-2-1-3-9-26)32(39)37-22-14-28(15-23-37)35-18-6-7-19-35/h1-3,8-11,24,27-28,33H,4-7,12-23H2
comment: UNC1215 was delevoped in a collaboration between the SGC (Structural Genomics Consortium) and the Center for Integrative Chemical Biology and Drug Discovery (CICBDD) at The University of North Carolina. It is the first chemical probe for a Kme (methyl-lysine recognition domain)-binding protein. UNC1215 is reported to be a potent and selective modulator of the Kme reading function of L3MBTL3, a member of the malignant brain tumor (MBT) family of chromatin interacting transcriptional repressors <Reference id=27122/>. Click here to link to the SGC's full list of epigenetics probes.
iupac name: N-phenyl-2,5-bis[4-(pyrrolidin-1-yl)piperidine-1-carbonyl]aniline
xref: CHEMBL2426364
approved: f
ligand name: UNC1215
type: SyntheticOrganicLigand

OICR-9429
in ch i key: DJOVLOYCGXNVPI-UHFFFAOYSA-N
in ch i: InChI=1S/C29H32F3N5O3/c1-35-7-9-37(10-8-35)26-6-5-22(21-4-2-3-20(15-21)19-36-11-13-40-14-12-36)16-25(26)34-28(39)23-18-33-27(38)17-24(23)29(30,31)32/h2-6,15-18H,7-14,19H2,1H3,(H,33,38)(H,34,39)
comment: OICR-9429 was developed in a collaboration between the SGC (Structural Genomics Consortium) and The Drug Discovery Program at the Ontario Institute for Cancer Research (OICR). It can be used as a chemical probe for WDR5 activity, WDR5 being a component of several chromatin regulatory complexes including the MLL1 (mixed lineage leukemia 1) complex. OICR-9429 antagonises the interaction between WDR5 and MLL or Histone 3 binding domains. Click here to link to the SGC's full list of epigenetics probes.
iupac name: N-[2-(4-methylpiperazin-1-yl)-5-[3-(morpholin-4-ylmethyl)phenyl]phenyl]-6-oxo-4-(trifluoromethyl)-1,6-dihydropyridine-3-carboxamide
approved: f
ligand name: OICR-9429
type: SyntheticOrganicLigand

IOX1
canonical SMILES: OC(=O)c1ccc(c2c1cccn2)O
isomeric SMILES: OC(=O)c1ccc(c2c1cccn2)O
in ch i key: JGRPKOGHYBAVMW-UHFFFAOYSA-N
in ch i: InChI=1S/C10H7NO3/c12-8-4-3-7(10(13)14)6-2-1-5-11-9(6)8/h1-5,12H,(H,13,14)
comment: IOX1 is a cell-permeable, broad-spectrum 2-oxoglutarate oxygenase inhibitor <Reference id=27117/>. This is a compound from the Structural Genomics Consortium's (SGC) Epigenetics Probes Collection.
iupac name: 8-hydroxyquinoline-5-carboxylic acid
xref: CHEMBL1230640
approved: f
ligand name: IOX1
type: SyntheticOrganicLigand

IOX2
in ch i key: CAOSCCRYLYQBES-UHFFFAOYSA-N
in ch i: InChI=1S/C19H16N2O5/c22-15(23)10-20-18(25)16-17(24)13-8-4-5-9-14(13)21(19(16)26)11-12-6-2-1-3-7-12/h1-9,24H,10-11H2,(H,20,25)(H,22,23)
comment: IOX2 is a selective, cell permeable inhibitor of the hypoxia inducible factor (HIF) prolyl-hydroxylase protein PHD2. This is a compound from the Structural Genomics Consortium's (SGC) Epigenetics Probes Collection.
iupac name: 2-[(1-benzyl-4-hydroxy-2-oxoquinoline-3-carbonyl)amino]acetic acid
xref: CHEMBL3186774
synonym: compound 6
approved: f
ligand name: IOX2
type: SyntheticOrganicLigand

amg-1
in ch i key: XYXNYQAJSYUYNZ-UHFFFAOYSA-N
in ch i: InChI=1S/C20H16N4O3S2/c1-12-2-4-13(5-3-12)15-9-28-19-22-23-20(24(15)19)29-10-18(25)21-14-6-7-16-17(8-14)27-11-26-16/h2-9H,10-11H2,1H3,(H,21,25)
comment: Amg-1 is reported as a reversible inhibitor of indoleamine 2,3-dioxygenase 1 (IDO1) <Reference id=27060/>.
iupac name: N-(1,3-benzodioxol-5-yl)-2-[[5-(4-methylphenyl)-[1,3]thiazolo[3,2-d][1,2,4]triazol-3-yl]sulfanyl]acetamide
approved: f
ligand name: amg-1
type: SyntheticOrganicLigand

indoximod
canonical SMILES: OC(=O)C(Cc1cn(c2c1cccc2)C)N
isomeric SMILES: OC(=O)[C@@H](Cc1cn(c2c1cccc2)C)N
in ch i key: ZADWXFSZEAPBJS-SNVBAGLBSA-N
in ch i: InChI=1S/C12H14N2O2/c1-14-7-8(6-10(13)12(15)16)9-4-2-3-5-11(9)14/h2-5,7,10H,6,13H2,1H3,(H,15,16)/t10-/m1/s1
comment: Indoximod is being investigated for its inhibitory action towards indoleamine 2,3-dioxygenase 1 (IDO1), a L-tryptophan degrading enzyme.
iupac name: (2R)-2-amino-3-(1-methylindol-3-yl)propanoic acid
xref: CHEMBL571209
synonym: D-1MT
synonym: 1MT
synonym: 1-methyl-D-tryptophan
approved: f
ligand name: indoximod
type: SyntheticOrganicLigand

epacadostat
isomeric SMILES: O=N/C(=c/1/[nH]onc1NCCNS(=O)(=O)N)/Nc1ccc(c(c1)Br)F
in ch i key: YPBKTZBXSBLTDK-PKNBQFBNSA-N
comment: Epacadostat (INCB024360) is an orally bioavailable, potent, small molecule inhibitor of indoleamine-2,3-dioxygenase 1 (IDO1) <Reference id=27054/><Reference id=30568/>, with therapeutic potential in immunodeficiency-associated abnormalities, including cancer.
iupac name: (3E)-3-[(3-bromo-4-fluoroanilino)-nitrosomethylidene]-4-[2-(sulfamoylamino)ethylamino]-1,2,5-oxadiazole
xref: CHEMBL3545369
synonym: INCB-24360
synonym: INCB 24360
synonym: INCB024360
synonym: IDO inhibitor 1
approved: f
ligand name: epacadostat
type: SyntheticOrganicLigand

compound 15 [PMID: 24900237]
in ch i key: GLGNXYJARSMNGJ-VKTIVEEGSA-N
in ch i: InChI=1S/C25H29ClN6O3/c1-3-32-18-10-9-17(22(35-2)15(18)5-4-6-19(32)33)29-25-28-12-16(26)24(31-25)30-21-14-8-7-13(11-14)20(21)23(27)34/h7-10,12-14,20-21H,3-6,11H2,1-2H3,(H2,27,34)(H2,28,29,30,31)/t13-,14+,20+,21-/m1/s1
comment: Compound 15 is the lead compound identified in a medicinal chemistry study to identify orally available anaplastic lymphoma kinase (ALK) inhibitors with antitumor activity <Reference id=27039/>.
iupac name: (1S,2S,3R,4R)-3-[[5-chloro-2-[(1-ethyl-6-methoxy-2-oxo-4,5-dihydro-3H-1-benzazepin-7-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide
xref: CHEMBL2042829
approved: f
ligand name: compound 15 [PMID: 24900237]
type: SyntheticOrganicLigand

compound 74 [PMID: 24793884]
in ch i key: CQNCHLJHIGRPDA-UHFFFAOYSA-N
in ch i: InChI=1S/C14H9Cl2N5OS/c15-6-1-2-7(8(16)5-6)10-11(12(17)22)23-13(21-10)9-3-4-19-14(18)20-9/h1-5H,(H2,17,22)(H2,18,19,20)
comment: Compound 74 is one of the analogues assessed in <Reference id=27038/> as a potential cell division cycle 7 (cdc7) inhibitor.
iupac name: 2-(2-aminopyrimidin-4-yl)-4-(2,4-dichlorophenyl)-1,3-thiazole-5-carboxamide
xref: CHEMBL3261514
approved: f
ligand name: compound 74 [PMID: 24793884]
type: SyntheticOrganicLigand

compound 77 [PMID: 24793884]
in ch i key: VCUXVXLUOHDHKK-UHFFFAOYSA-N
comment: Compound 77 is one of the analogues assessed in <Reference id=27038/> as a potential cell division cycle 7 (cdc7) inhibitor.
iupac name: 2-(2-aminopyrimidin-4-yl)-4-(2-chloro-4-methoxyphenyl)-1,3-thiazole-5-carboxamide
xref: CHEMBL3261517
approved: f
ligand name: compound 77 [PMID: 24793884]
type: SyntheticOrganicLigand

SB-431542
in ch i key: FHYUGAJXYORMHI-UHFFFAOYSA-N
in ch i: InChI=1S/C22H16N4O3/c23-21(27)13-4-6-14(7-5-13)22-25-19(20(26-22)16-3-1-2-10-24-16)15-8-9-17-18(11-15)29-12-28-17/h1-11H,12H2,(H2,23,27)(H,25,26)
comment: SB-431542 is reported as an ATP-competitive inhibitor of a group of related activin receptor-like kinases; ALK5 (TGFBR1) <Reference id=27035/>, ALK4 (ACVR1B) and ALK7 (ACVR1C) <Reference id=27034/>, which belong to the type I receptor serine/threonine kinase family. SB-431542 acts as a selective inhibitor of endogenous activin and TGFβ signalling but has no effect on bone morphogenetic protein signalling through the more divergent ALKs of the type I receptor serine/threonine kinase family.
iupac name: 4-[4-(1,3-benzodioxol-5-yl)-5-pyridin-2-yl-1H-imidazol-2-yl]benzamide
xref: CHEMBL440084
synonym: compound 14
synonym: SB431542
synonym: SB 431542
approved: f
ligand name: SB-431542
type: SyntheticOrganicLigand

CCT244747
in ch i key: IENLGMOXAQMNEH-CYBMUJFWSA-N
in ch i: InChI=1S/C20H24N8O2/c1-13(11-27(2)3)30-20-16(7-21)22-10-19(26-20)25-18-6-17(29-5)15(9-23-18)14-8-24-28(4)12-14/h6,8-10,12-13H,11H2,1-5H3,(H,23,25,26)/t13-/m1/s1
comment: CCT244747 is reported as checkpoint kinase 1 (CHK1)-selective tool compound suitable for in vitro and in vivo pharmacological studies <Reference id=27033/>,
iupac name: 3-[(2R)-1-(dimethylamino)propan-2-yl]oxy-5-[[4-methoxy-5-(1-methylpyrazol-4-yl)pyridin-2-yl]amino]pyrazine-2-carbonitrile
xref: CHEMBL2203843
synonym: compound 26 [PMID: 23082860]
approved: f
ligand name: CCT244747
type: SyntheticOrganicLigand

KH-CB19
canonical SMILES: CCOC(=O)c1c(C(=CN)C#N)c2c(n1C)c(Cl)c(cc2)Cl
isomeric SMILES: CCOC(=O)c1c(/C(=C/N)/C#N)c2c(n1C)c(Cl)c(cc2)Cl
in ch i key: CXJCGSPAPOTTSF-VURMDHGXSA-N
comment: KH-CB19 is an inhibitor of dual specificity CDC-like kinase 1 (CLK1) <Reference id=15289/>. It was a preclinical lead compound.
iupac name: ethyl 3-[(E)-2-amino-1-cyanoethenyl]-6,7-dichloro-1-methylindole-2-carboxylate
xref: CHEMBL1236620
synonym: KH CB19
approved: f
ligand name: KH-CB19
type: SyntheticOrganicLigand

compound 14k [PMID: 21982499]
in ch i key: WNOHFJIMKSDPHP-UHFFFAOYSA-N
in ch i: InChI=1S/C20H13ClN6/c21-16-6-1-2-7-17(16)25-20-13-8-9-22-10-15(13)12-4-3-5-14(18(12)26-20)19-23-11-24-27-19/h1-11H,(H,25,26)(H,23,24,27)
comment: Compound 14k was identified as a potent dual inhibitor of Pim1 and Pim2 <Reference id=27032/>.
iupac name: N-(2-chlorophenyl)-7-(1H-1,2,4-triazol-5-yl)benzo[c][2,6]naphthyridin-5-amine
xref: CHEMBL1915438
approved: f
ligand name: compound 14k [PMID: 21982499]
type: SyntheticOrganicLigand

compound R-16 [PMID: 21967808]
in ch i key: HGSNUBHWAMMKIR-JOCHJYFZSA-N
comment: Compound R-16 is reported in <Reference id=27031/>, a study to improve oral availability of 2,4-diaminopyrimidine c-Met (hepatocyte growth factor receptor) inhibitors.
iupac name: N-[(3R)-8-[[5-chloro-4-[2-fluoro-6-(methylcarbamoyl)anilino]pyrimidin-2-yl]amino]-5,5-dimethyl-2-oxo-3,4-dihydro-1H-1-benzazepin-3-yl]pyrrolidine-1-carboxamide
xref: CHEMBL1939491
approved: f
ligand name: compound R-16 [PMID: 21967808]
type: SyntheticOrganicLigand

compound 66 [PMID: 21802293]
in ch i key: WGFNXGPBPIJYLI-UHFFFAOYSA-N
comment: Compound 66 is reported in <Reference id=27030/>, a medicinal chemistry/structure-based design study to identify improved inhibitors of BRAFV600E.
iupac name: 2,6-difluoro-3-[(3-fluorophenyl)sulfonylamino]-N-(3-methoxy-1H-pyrazolo[3,4-b]pyridin-5-yl)benzamide
xref: CHEMBL1822258
approved: f
ligand name: compound 66 [PMID: 21802293]
type: SyntheticOrganicLigand

compound 4g [PMID: 21316219]
in ch i key: CDVMXMZPDJHSCC-UHFFFAOYSA-N
in ch i: InChI=1S/C22H16N4O/c27-20(15-5-2-1-3-6-15)12-14-8-9-16-13-19(24-18(16)11-14)22-21-17(25-26-22)7-4-10-23-21/h1-11,13,24H,12H2,(H,25,26)
comment: Compound 4g is an alkoxy derivative of compound 4a <Reference id=27029/> and was reported in a medicinal chemistry/structure aided design study to identify improved inhibitors of interleukin-2 inducible T-cell kinase (ITK).
iupac name: 2-[(2Z)-2-(1,2-dihydropyrazolo[4,3-b]pyridin-3-ylidene)indol-6-yl]-1-phenylethanone
xref: CHEMBL1684662
approved: f
ligand name: compound 4g [PMID: 21316219]
type: SyntheticOrganicLigand

compound 27 [PMID: 21123062]
in ch i key: KHBUKOVUBUJCGM-UHFFFAOYSA-N
comment: Compound 27 is reported in a medicinal chemistry study to identify novel c-MET (hepatocyte growth factor receptor) inhibitors <Reference id=27028/>.
iupac name: 2-[[5-chloro-2-[(1-ethyl-5,5-dimethyl-2-oxo-3,4-dihydro-1-benzazepin-8-yl)amino]pyrimidin-4-yl]amino]-3-fluoro-N-methylbenzamide
xref: CHEMBL1644812
approved: f
ligand name: compound 27 [PMID: 21123062]
type: SyntheticOrganicLigand

compound 35 [PMID: 20684608]
in ch i key: GFWDPXHTWJXOEI-RUZDIDTESA-N
in ch i: InChI=1S/C27H33N5O3/c1-32-9-7-18(8-10-32)17-35-26-13-19(22-15-29-30-16-22)4-6-24(26)31-27(33)25-12-21-11-23(34-2)5-3-20(21)14-28-25/h3-6,11,13,15-16,18,25,28H,7-10,12,14,17H2,1-2H3,(H,29,30)(H,31,33)/t25-/m1/s1
comment: Compound 35 is reported in <Reference id=27027/> as a novel inhibitor of Rho kinases.
iupac name: (3R)-6-methoxy-N-[2-[(1-methylpiperidin-4-yl)methoxy]-4-(1H-pyrazol-4-yl)phenyl]-1,2,3,4-tetrahydroisoquinoline-3-carboxamide
xref: CHEMBL1215304
approved: f
ligand name: compound 35 [PMID: 20684608]
type: SyntheticOrganicLigand

compound 5n [PMID: 20483621]
in ch i key: AHZCYZMNFBGXAC-UHFFFAOYSA-N
in ch i: InChI=1S/C24H24ClF3N6/c25-19-1-2-20(24(26,27)28)18(11-19)15-34-10-7-31-23-21(34)12-17(14-32-23)16-3-4-30-22(13-16)33-8-5-29-6-9-33/h1-4,11-14,29H,5-10,15H2,(H,31,32)
comment: Compound 5n is reported in <Reference id=27026/> as a novel inhibitor anaplastic lymphoma receptor tyrosine kinase (ALK).
iupac name: 1-[[5-chloro-2-(trifluoromethyl)phenyl]methyl]-7-(2-piperazin-1-ylpyridin-4-yl)-3,4-dihydro-2H-pyrido[2,3-b]pyrazine
xref: CHEMBL1163566
approved: f
ligand name: compound 5n [PMID: 20483621]
type: SyntheticOrganicLigand

compound 5g [PMID: 20483621]
in ch i key: CSYSNPSPLOLFFI-UHFFFAOYSA-N
in ch i: InChI=1S/C24H26Cl2N6/c1-30-8-10-31(11-9-30)23-5-2-17(14-28-23)18-13-22-24(29-15-18)27-6-7-32(22)16-19-12-20(25)3-4-21(19)26/h2-5,12-15H,6-11,16H2,1H3,(H,27,29)
comment: Compound 5g is reported in <Reference id=27026/> as a novel inhibitor of anaplastic lymphoma receptor tyrosine kinase (ALK).
iupac name: 1-[(2,5-dichlorophenyl)methyl]-7-[6-(4-methylpiperazin-1-yl)pyridin-3-yl]-3,4-dihydro-2H-pyrido[2,3-b]pyrazine
xref: CHEMBL1164181
approved: f
ligand name: compound 5g [PMID: 20483621]
type: SyntheticOrganicLigand

compound 5m [PMID: 20483621]
in ch i key: JVVGHVJDZJSKRA-UHFFFAOYSA-N
comment: Compound 5m is reported in <Reference id=27026/> as an inhibitor of anaplastic lymphoma receptor tyrosine kinase (ALK).
iupac name: [4-[1-[[5-chloro-2-(trifluoromethyl)phenyl]methyl]-3,4-dihydro-2H-pyrido[2,3-b]pyrazin-7-yl]phenyl]-(4-pyrrolidin-1-ylpiperidin-1-yl)methanone
xref: CHEMBL1163559
approved: f
ligand name: compound 5m [PMID: 20483621]
type: SyntheticOrganicLigand

compound 22 [PMID: 20462760]
in ch i key: SKYALJGMRAGHEN-UHFFFAOYSA-N
in ch i: InChI=1S/C20H18ClN3O2/c21-16-11-15-13(8-9-22-19(15)25)10-17(16)24-20(26)18(23-14-6-7-14)12-4-2-1-3-5-12/h1-5,8-11,14,18,23H,6-7H2,(H,22,25)(H,24,26)
comment: Compound 22 is reported in <Reference id=26992/> as a potent inhibitor of Rho kinases 1 and 2 (ROCK1 and ROCK2).
iupac name: N-(7-chloro-1-oxo-1,2-dihydroisoquinolin-6-yl)-2-(cyclopropylamino)-2-phenylacetamide
xref: CHEMBL1084106
approved: f
ligand name: compound 22 [PMID: 20462760]
type: SyntheticOrganicLigand

A-443654
in ch i key: YWTBGJGMTBHQTM-IBGZPJMESA-N
in ch i: InChI=1S/C24H23N5O/c1-15-22-10-16(6-7-24(22)29-28-15)17-9-20(13-26-11-17)30-14-19(25)8-18-12-27-23-5-3-2-4-21(18)23/h2-7,9-13,19,27H,8,14,25H2,1H3,(H,28,29)/t19-/m0/s1
comment: A-443654 is an ATP-competitive inhibitor of all three Akt (protein kinase B) subtypes <Reference id=26756/>, but causes paradixical hyperphosphorylation of two regulatory amino acid residues (Thr308 and Ser473) of the Akt protein <Reference id=27024/><Reference id=27025/>. A-443654 exhibits modest selectivity for Akt, compared to other AGC family kinases, such as PKA and PKC <Reference id=26756/>.
iupac name: (2S)-1-(1H-indol-3-yl)-3-[5-(3-methyl-2H-indazol-5-yl)pyridin-3-yl]oxypropan-2-amine
xref: CHEMBL379300
synonym: A443654
synonym: A 443654
approved: f
ligand name: A-443654
type: SyntheticOrganicLigand

ML323
in ch i key: VUIRVWPJNKZOSS-UHFFFAOYSA-N
in ch i: InChI=1S/C23H24N6/c1-16(2)20-6-4-5-7-21(20)23-24-14-17(3)22(27-23)25-15-18-8-10-19(11-9-18)29-13-12-26-28-29/h4-14,16H,15H2,1-3H3,(H,24,25,27)
comment: USP1/UAF1 deubiquitinase inhibitor with anticancer activity
iupac name: 5-methyl-2-(2-propan-2-ylphenyl)-N-[[4-(triazol-1-yl)phenyl]methyl]pyrimidin-4-amine
xref: CHEMBL3182437
synonym: ML 323
synonym: ML-323
approved: f
ligand name: ML323
type: SyntheticOrganicLigand

Ro-0505124
in ch i key: YGEYFDLYGXSZCP-UHFFFAOYSA-N
in ch i: InChI=1S/C23H25N5O3S/c1-27-8-10-28(11-9-27)17-5-3-16(4-6-17)25-23-26-22(24)21(32-23)20(29)15-2-7-18-19(14-15)31-13-12-30-18/h2-7,14H,8-13,24H2,1H3,(H,25,26)
comment: Ro-0505124 is a potent and selective ATP-competitive inhibitor of cyclin-dependent kinase 4 (CDK4) <Reference id=27022/><Reference id=27023/>. Ro-0505124 is >100 fold selective for CDK4 compared to CDKs 1 and -2 <Reference id=27023/>.
iupac name: [4-amino-2-[[4-(4-methylpiperazin-1-yl)phenyl]amino]-1,3-thiazol-5-yl]-(2,3-dihydro-1,4-benzodioxin-7-yl)methanone
xref: CHEMBL1956070
synonym: RO0505124
approved: f
ligand name: Ro-0505124
type: SyntheticOrganicLigand

BMS-833923
in ch i key: KLRRGBHZCJLIEL-UHFFFAOYSA-N
in ch i: InChI=1S/C30H27N5O/c1-20-12-13-21(19-31-2)18-27(20)33-29(36)23-14-16-24(17-15-23)32-30-34-26-11-7-6-10-25(26)28(35-30)22-8-4-3-5-9-22/h3-18,31H,19H2,1-2H3,(H,33,36)(H,32,34,35)
comment: BMS-833923 is a high affinity antagonist of the class frizzled GPCR, smoothened (SMO) <Reference id=27019/><Reference id=27020/>. BMS-833923 is compound 163 in patent US8222263 <Reference id=27021/>.
iupac name: N-[2-methyl-5-(methylaminomethyl)phenyl]-4-[(4-phenylquinazolin-2-yl)amino]benzamide
synonym: XL139
synonym: XL-139
synonym: BMS833923
synonym: BMS 833923
synonym: XL 139
approved: f
ligand name: BMS-833923
type: SyntheticOrganicLigand

esmolol
canonical SMILES: COC(=O)CCc1ccc(cc1)OCC(CNC(C)C)O
isomeric SMILES: COC(=O)CCc1ccc(cc1)OCC(CNC(C)C)O
in ch i key: AQNDDEOPVVGCPG-UHFFFAOYSA-N
in ch i: InChI=1S/C16H25NO4/c1-12(2)17-10-14(18)11-21-15-7-4-13(5-8-15)6-9-16(19)20-3/h4-5,7-8,12,14,17-18H,6,9-11H2,1-3H3
comment: Esmolol is a β-blocker. Marketed formulations may contain esmolol hydrochloride (PubChem CID 104769).
iupac name: methyl 3-(4-{2-hydroxy-3-[(propan-2-yl)amino]propoxy}phenyl)propanoate
xref: CHEMBL768
synonym: Brevibloc®
synonym: SL-8052
approved: t
ligand name: esmolol
type: SyntheticOrganicLigand

glasdegib
in ch i key: SFNSLLSYNZWZQG-VQIMIIECSA-N
in ch i: InChI=1S/C21H22N6O/c1-27-11-10-16(24-21(28)23-15-8-6-14(13-22)7-9-15)12-19(27)20-25-17-4-2-3-5-18(17)26-20/h2-9,16,19H,10-12H2,1H3,(H,25,26)(H2,23,24,28)/t16-,19-/m1/s1
comment: Glasdegib is a potent and orally active inhibitor of the hedgehog signalling pathway, that acts as an antagonist of the class frizzled GPCR, smoothened (SMO) <Reference id=27018/>.
iupac name: 1-[(2R,4R)-2-(1H-benzimidazol-2-yl)-1-methylpiperidin-4-yl]-3-(4-cyanophenyl)urea
xref: CHEMBL2043437
synonym: PF-04449913
synonym: PF 04449913
synonym: Daurismo®
approved: t
ligand name: glasdegib
type: SyntheticOrganicLigand

TAK-441
in ch i key: ZADWXQMNNVICKB-UHFFFAOYSA-N
in ch i: InChI=1S/C28H31F3N4O6/c1-3-19-13-20-23(27(40)35(19)14-21(37)17-7-5-4-6-8-17)25(41-16-28(29,30)31)24(33(20)2)26(39)32-18-9-11-34(12-10-18)22(38)15-36/h4-8,13,18,36H,3,9-12,14-16H2,1-2H3,(H,32,39)
comment: TAK-441 is an inhibitor of the hedgehog signalling pathway, acting as an antagonist of the class frizzled GPCR, smoothened (SMO) <Reference id=27017/>.
iupac name: 6-ethyl-N-[1-(2-hydroxyacetyl)piperidin-4-yl]-1-methyl-4-oxo-5-phenacyl-3-(2,2,2-trifluoroethoxy)pyrrolo[3,2-c]pyridine-2-carboxamide
xref: CHEMBL2205230
approved: f
ligand name: TAK-441
type: SyntheticOrganicLigand

sonidegib
in ch i key: VZZJRYRQSPEMTK-CALCHBBNSA-N
in ch i: InChI=1S/C26H26F3N3O3/c1-16-14-32(15-17(2)34-16)24-12-9-20(13-30-24)31-25(33)23-6-4-5-22(18(23)3)19-7-10-21(11-8-19)35-26(27,28)29/h4-13,16-17H,14-15H2,1-3H3,(H,31,33)/t16-,17+
comment: Sonidegib (INN formerly erismodegib, but replaced in 2012) is an orally active inhibitor of the hedgehog signalling pathway, acting as an antagonist of the class frizzled GPCR, smoothened (SMO) <Reference id=27016/><Reference id=23531/>. The first hedgehog pathway inhibitor to be approved was <Ligand id=6975/> (2012).
iupac name: N-[6-[(2S,6R)-2,6-dimethylmorpholin-4-yl]pyridin-3-yl]-2-methyl-3-[4-(trifluoromethoxy)phenyl]benzamide
xref: CHEMBL2105737
synonym: LDE-225
synonym: NVP-LDE225
synonym: NVP-LDE 225
synonym: erismodegib (deleted INN)
synonym: Odomzo®
synonym: LDE225
approved: t
ligand name: sonidegib
type: SyntheticOrganicLigand

saridegib
in ch i key: HZLFFNCLTRVYJG-WWGOJCOQSA-N
in ch i: InChI=1S/C29H48N2O3S/c1-17-12-26-27(30-16-17)19(3)29(34-26)11-9-22-23-7-6-20-13-21(31-35(5,32)33)8-10-28(20,4)25(23)14-24(22)18(2)15-29/h17,19-23,25-27,30-31H,6-16H2,1-5H3/t17-,19+,20+,21+,22-,23-,25-,26+,27-,28-,29-/m0/s1
comment: Saridegib is an orally active inhibitor of the hedgehog signalling pathway, acting as an antagonist of the class frizzled GPCR, smoothened (SMO) <Reference id=27015/>.
iupac name: N-[(3R,3'R,3'aS,4aR,6'S,6aR,6bS,7'aR,9S,12aS,12bS)-3',6',11,12b-tetramethylspiro[1,2,3,4,4a,5,6,6a,6b,7,8,10,12,12a-tetradecahydronaphtho[2,1-a]azulene-9,2'-3a,4,5,6,7,7a-hexahydro-3H-furo[3,2-b]pyridine]-3-yl]methanesulfonamide
xref: CHEMBL538867
synonym: IPI 926
synonym: IPI-926
approved: f
ligand name: saridegib
type: SyntheticOrganicLigand

compound 11d [DOI: 10.1039/c0md00194e]
in ch i key: YHIPVWFQESXDIE-KRWDZBQOSA-N
in ch i: InChI=1S/C23H25N3O5/c1-29-19-4-6-21-16(10-19)9-17(14-31-21)23(28)26-20-5-3-15(18-12-24-25-13-18)11-22(20)30-8-2-7-27/h3-6,10-13,17,27H,2,7-9,14H2,1H3,(H,24,25)(H,26,28)/t17-/m0/s1
comment: Compound 11d is an analogue assessed in a medicinal chemistry study to identify novel inhibitors of Rho kinase 2 (ROCK2) <Reference id=27014/>.
iupac name: (3S)-N-[2-(3-hydroxypropoxy)-4-(1H-pyrazol-4-yl)phenyl]-6-methoxy-3,4-dihydro-2H-1-benzopyran-3-carboxamide
xref: CHEMBL3221815
approved: f
ligand name: compound 11d [DOI: 10.1039/c0md00194e]
type: SyntheticOrganicLigand

compound 17d [PMID: 23099093]
in ch i key: CJPMSUUANYLPET-UHFFFAOYSA-N
in ch i: InChI=1S/C25H34N6O2/c32-24(19-3-1-4-19)27-12-2-11-26-23-22(18-5-6-18)17-28-25(30-23)29-20-7-9-21(10-8-20)31-13-15-33-16-14-31/h7-10,17-19H,1-6,11-16H2,(H,27,32)(H2,26,28,29,30)
comment: Compound 17d is an analogue assessed in a medicinal chemistry study to find novel, potent inhibitors of the TANK-binding kinase 1 (TBK1) and IKK-epsilon (IKKε) kinases <Reference id=27013/>.
iupac name: N-{3-[(5-cyclopropyl-2-{[4-(morpholin-4-yl)phenyl]amino}pyrimidin-4-yl)amino]propyl}cyclobutanecarboxamide
xref: CHEMBL2207198
approved: f
ligand name: compound 17d [PMID: 23099093]
type: SyntheticOrganicLigand

compound 8 [PMID: 24044867]
in ch i key: UQHKXSZPEUNUDH-UHFFFAOYSA-N
in ch i: InChI=1S/C24H21N3O3/c1-28-21-10-16(11-22(29-2)23(21)30-3)17-9-18-19(13-27-24(18)26-12-17)14-4-5-20-15(8-14)6-7-25-20/h4-13,25H,1-3H3,(H,26,27)
comment: Compound 8 is one of the analogues assessed in a medicinal chemistry study to identify orally bioavailable, brain penetrant inhibitors of mixed lineage kinase 3 (MLK3) <Reference id=26846/>.
iupac name: 5-[5-(3,4,5-trimethoxyphenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]-1H-indole
xref: CHEMBL2436980
approved: f
ligand name: compound 8 [PMID: 24044867]
type: SyntheticOrganicLigand

compound 15b [PMID: 16539403]
canonical SMILES: OCCCn1cnc2c1cc(cc2)c1c2CCCn2nc1c1ccccn1
isomeric SMILES: OCCCn1cnc2c1cc(cc2)c1c2CCCn2nc1c1ccccn1
in ch i key: SYCWRTUPLPDKDX-UHFFFAOYSA-N
in ch i: InChI=1S/C21H21N5O/c27-12-4-10-25-14-23-16-8-7-15(13-19(16)25)20-18-6-3-11-26(18)24-21(20)17-5-1-2-9-22-17/h1-2,5,7-9,13-14,27H,3-4,6,10-12H2
comment: Compound 15b was desigend and assessed in a medicinal chemistry study to identify selective inhibitors of transforming growth factor-beta type I receptor kinase (TGFβR1) <Reference id=27012/>.
iupac name: 3-[6-(2-pyridin-2-yl-5,6-dihydro-4H-pyrrolo[2,1-e]pyrazol-3-yl)benzimidazol-1-yl]propan-1-ol
xref: CHEMBL203619
approved: f
ligand name: compound 15b [PMID: 16539403]
type: SyntheticOrganicLigand

compound 30 [PMID: 17280833]
in ch i key: CYXPHNZJEDAZDD-UHFFFAOYSA-N
in ch i: InChI=1S/C32H32N4O2/c1-3-9-24(10-4-1)17-18-33-31-29-28(25-11-5-2-6-12-25)30(38-32(29)35-23-34-31)26-13-15-27(16-14-26)37-22-21-36-19-7-8-20-36/h1-6,9-16,23H,7-8,17-22H2,(H,33,34,35)
comment: Compound 30 was designed and assessed in a medicinal chemistry/structure-activity study to identify potent and selective inhibitors of the Src family tyrosine kinase, Lck <Reference id=27007/>.
iupac name: 5-phenyl-N-(2-phenylethyl)-6-[4-(2-pyrrolidin-1-ylethoxy)phenyl]furo[3,2-e]pyrimidin-4-amine
xref: CHEMBL247667
approved: f
ligand name: compound 30 [PMID: 17280833]
type: SyntheticOrganicLigand

compound 5 [PMID: 23232060]
in ch i key: GOMSKBLQVUFHHS-UHFFFAOYSA-N
in ch i: InChI=1S/C25H27N5O2/c1-29-10-12-30(13-11-29)22-6-5-20(16-24(22)32-3)28-25-15-19(8-9-27-25)21-14-18(17-26)4-7-23(21)31-2/h4-9,14-16H,10-13H2,1-3H3,(H,27,28)
comment: Compound 5 was reported in a medicinal chemistry article describing the search for potent and selective inhibitors of TRAF2 and NCK interacting kinase (TNIK) <Reference id=26974/>.
iupac name: 4-methoxy-3-[2-[3-methoxy-4-(4-methylpiperazin-1-yl)anilino]pyridin-4-yl]benzonitrile
xref: CHEMBL2312144
approved: f
ligand name: compound 5 [PMID: 23232060]
type: SyntheticOrganicLigand

compound 18 [PMID: 20873740]
canonical SMILES: Nc1nccc(n1)c1[nH]c(c(c1)C(=O)N)c1ccccc1
isomeric SMILES: Nc1nccc(n1)c1[nH]c(c(c1)C(=O)N)c1ccccc1
in ch i key: VOQXQYXTZZHYBF-UHFFFAOYSA-N
in ch i: InChI=1S/C15H13N5O/c16-14(21)10-8-12(11-6-7-18-15(17)20-11)19-13(10)9-4-2-1-3-5-9/h1-8,19H,(H2,16,21)(H2,17,18,20)
comment: Compound 18 was identified in a medicinal chemistry study to identify novel inhibitors of cell division cycle 7 (Cdc7) kinase <Reference id=27006/>.
iupac name: 5-(2-aminopyrimidin-4-yl)-2-phenyl-1H-pyrrole-3-carboxamide
xref: CHEMBL1270230
approved: f
ligand name: compound 18 [PMID: 20873740]
type: SyntheticOrganicLigand

compound 1 [PMID: 21742770]
in ch i key: LZQFMCFJCXQTTG-UHFFFAOYSA-N
in ch i: InChI=1S/C25H28N6O2/c1-29-12-14-30(15-13-29)22-10-5-19(16-23(22)33-3)27-24-11-4-18-17-26-31(25(18)28-24)20-6-8-21(32-2)9-7-20/h4-11,16-17H,12-15H2,1-3H3,(H,27,28)
comment: Compound 1 was identified as a potent inhibitor of serine/threonine kinase 33 (STK33) in a high-throughput screen of a compound library <Reference id=27004/>.
iupac name: N-[3-methoxy-4-(4-methylpiperazin-1-yl)phenyl]-1-(4-methoxyphenyl)pyrazolo[3,4-b]pyridin-6-amine
xref: CHEMBL2203524
approved: f
ligand name: compound 1 [PMID: 21742770]
type: SyntheticOrganicLigand

compound 13r [PMID: 23639540]
in ch i key: XBGWAKUQSRNWMA-UHFFFAOYSA-N
in ch i: InChI=1S/C26H24N6/c1-30-12-14-31(15-13-30)21-8-6-19(7-9-21)20-16-28-26-24(17-29-32(26)18-20)22-10-11-27-25-5-3-2-4-23(22)25/h2-11,16-18H,12-15H2,1H3
comment: Compound 13r is one of the analogues assessed in a study to identify selective inhibitors of bone morphogenetic protein receptor isotypes <Reference id=26903/>.
iupac name: 4-[6-[4-(4-methylpiperazin-1-yl)phenyl]pyrazolo[1,5-a]pyrimidin-3-yl]quinoline
xref: CHEMBL2385596
approved: f
ligand name: compound 13r [PMID: 23639540]
type: SyntheticOrganicLigand

CEP-11981
in ch i key: AEULIVPVIDOLIN-UHFFFAOYSA-N
in ch i: InChI=1S/C28H27N7O/c1-15(2)13-35-22-8-5-16(32-28-29-9-4-10-30-28)11-18(22)24-19-12-31-27(36)25(19)23-17(26(24)35)6-7-21-20(23)14-34(3)33-21/h4-5,8-11,14-15H,6-7,12-13H2,1-3H3,(H,31,36)(H,29,30,32)
comment: CEP-11981 is reported as a novel oncology therapeutic agent targeting the pro-angiogenic actions of receptor tyrosine kinases such as the VEGFRs, FGFR1 and TIE-2 <Reference id=27003/>.
xref: CHEMBL2010872
synonym: compound 11b [PMID 22148921]
synonym: CEP11981
synonym: CEP 11981
approved: f
ligand name: CEP-11981
type: SyntheticOrganicLigand

compound 13 [PMID: 15925511]
in ch i key: GXGUVSXXUOACEX-UHFFFAOYSA-N
in ch i: InChI=1S/C21H12N2O2S2/c24-21(25)13-6-5-12-10-15-16(11-14(12)9-13)23-20(18-4-2-8-27-18)19(22-15)17-3-1-7-26-17/h1-11H,(H,24,25)
comment: Compound 13 is a derivative assessed in a medicinal chemistry study to identify novel selective inhibitors of SRSF protein kinase 1 (SRPK1) <Reference id=27002/>.
iupac name: 2,3-di(thiophen-2-yl)benzo[g]quinoxaline-8-carboxylic acid
xref: CHEMBL426445
approved: f
ligand name: compound 13 [PMID: 15925511]
type: SyntheticOrganicLigand

compound 21 [PMID: 24900635]
in ch i key: QQTPMHCXBYRWFQ-UHFFFAOYSA-N
in ch i: InChI=1S/C27H19F4N5O/c28-23-8-7-18(27(29,30)31)12-24(23)36-26(37)35-20-6-2-4-16(10-20)22-14-34-25-21(22)11-17(13-33-25)15-3-1-5-19(32)9-15/h1-14H,32H2,(H,33,34)(H2,35,36,37)
comment: Compound 21 is a derivative synthesised and assessed in a medicinal chemistry study to identify potent small molecule inhibitors of receptor (TNFRSF)-interacting serine-threonine kinase 1 (RIPK1) <Reference id=26995/>.
iupac name: 1-[3-[5-(3-aminophenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]phenyl]-3-[2-fluoro-5-(trifluoromethyl)phenyl]urea
xref: CHEMBL3109212
approved: f
ligand name: compound 21 [PMID: 24900635]
type: SyntheticOrganicLigand

compound 19a [PMID: 21855335]
in ch i key: MEQKJTZVPMNRIL-UHFFFAOYSA-N
in ch i: InChI=1S/C25H27ClN8O/c1-25(2)14-27-7-8-34(25)24(35)18-6-5-17(9-19(18)26)31-22-23-28-12-21(16-10-29-30-11-16)33(23)13-20(32-22)15-3-4-15/h5-6,9-13,15,27H,3-4,7-8,14H2,1-2H3,(H,29,30)(H,31,32)
comment: Compound 19a is a derivative identified in a medicinal chemistry study as a potent inhibitor of the Src family kinase, protein tyrosine kinase 6 (PTK6, aka Brk) <Reference id=26994/>.
iupac name: [2-chloro-4-[[6-cyclopropyl-3-(1H-pyrazol-4-yl)imidazo[1,2-a]pyrazin-8-yl]amino]phenyl]-(2,2-dimethylpiperazin-1-yl)methanone
xref: CHEMBL1836842
approved: f
ligand name: compound 19a [PMID: 21855335]
type: SyntheticOrganicLigand

compound 3 [PMID: 19097791]
in ch i key: KKMLIJHOUUKCSW-UHFFFAOYSA-N
in ch i: InChI=1S/C26H26N6O2/c1-31-10-12-32(13-11-31)21-5-3-4-19-25(21)28-26(27-19)24-18-8-6-16(14-20(18)29-30-24)17-7-9-22(33)23(15-17)34-2/h3-9,14-15,33H,10-13H2,1-2H3,(H,27,28)(H,29,30)
comment: Compound 3 is one of the analogues assessed in the search for PKCζ selective inhibitors <Reference id=26993/>. Compound 3 is equipotent against PKCζ and CDK2 kinase activities <Reference id=26993/>. PubChem CID 91623358 represents an alternative tautomer of this chemical structure.
iupac name: 2-methoxy-4-{3-[4-(4-methylpiperazin-1-yl)-1H-1,3-benzodiazol-2-yl]-1H-indazol-6-yl}phenol
xref: CHEMBL514197
approved: f
ligand name: compound 3 [PMID: 19097791]
type: SyntheticOrganicLigand

compound 32 [PMID: 20471253]
in ch i key: XBFAFSAUQFDEOK-JKSUJKDBSA-N
comment: Compound 32 was identified as a Rho kinase 2 (ROCK2) inhibitor <Reference id=26991/>.
iupac name: (3S,4R)-N-(7-chloro-1-oxo-1,2-dihydroisoquinolin-6-yl)-4-(4-chlorophenyl)pyrrolidine-3-carboxamide
xref: CHEMBL1082821
approved: f
ligand name: compound 32 [PMID: 20471253]
type: SyntheticOrganicLigand

PD166285
in ch i key: IFPPYSWJNWHOLQ-UHFFFAOYSA-N
comment: PD166285 was originally reported as a tyrosine kinase inhibitor <Reference id=26986/><Reference id=26987/><Reference id=26988/>, and has subsequently been identified as an inhibitor of Wee1 <Reference id=26989/> and Myt1 (PKMYT1) <Reference id=26990/>, two cyclin-dependent kinase (CDK) inhibitory kinases involved in regulating the cell cycle.
iupac name: 6-(2,6-dichlorophenyl)-2-[[4-(2-diethylaminoethoxy)phenyl]amino]-8-methylpyrido[6,5-d]pyrimidin-7-one
xref: CHEMBL49120
synonym: PD0166285
synonym: PD-166285
synonym: PD 166285
synonym: PD-0166285
approved: f
ligand name: PD166285
type: SyntheticOrganicLigand

flibanserin
in ch i key: PPRRDFIXUUSXRA-UHFFFAOYSA-N
in ch i: InChI=1S/C20H21F3N4O/c21-20(22,23)15-4-3-5-16(14-15)26-11-8-25(9-12-26)10-13-27-18-7-2-1-6-17(18)24-19(27)28/h1-7,14H,8-13H2,(H,24,28)
comment: Flibanserin is reported as a serotonin 5-HT1A agonist and 5-HT2A antagonist <Reference id=26982/>. The compound was originally investigated as a antidepressant <Reference id=26983/><Reference id=26984/>.
iupac name: 3-[2-[4-[3-(trifluoromethyl)phenyl]piperazin-1-yl]ethyl]-1H-benzimidazol-2-one
xref: CHEMBL231068
synonym: BIMT-17
synonym: Girosa® (proposed trade name)
synonym: Addyi®
approved: t
ligand name: flibanserin
type: SyntheticOrganicLigand

compound 1 [PMID: 20005102]
in ch i key: XONRTPBYDAFIRW-NRFANRHFSA-N
in ch i: InChI=1S/C28H25N5O2/c1-17-24-11-18(6-7-27(24)33-32-17)25-12-22(14-31-28(25)19-8-9-34-15-19)35-16-21(29)10-20-13-30-26-5-3-2-4-23(20)26/h2-9,11-15,21,30H,10,16,29H2,1H3,(H,32,33)/t21-/m0/s1
comment: Compound 1 was used as the starting molecular structure for the design and development of AKT (protein kinase B) inhibitors with improved drug-like properties and kinase selectivity <Reference id=26981/>.
iupac name: 5-{5-[(2S)-2-amino-3-(1H-indol-3-yl)propoxy]-2-(furan-3-yl)pyridin-3-yl}-3-methyl-2H-indazole
xref: CHEMBL593490
approved: f
ligand name: compound 1 [PMID: 20005102]
type: SyntheticOrganicLigand

compound 31 [PMID: 20936789]
in ch i key: YPKLAWUGDWZBMV-OUCADQQQSA-N
in ch i: InChI=1S/C21H28N4O5/c1-11-12(2)25(7-6-14(11)21(26)27)20-19(22)23-10-15(24-20)13-8-16(28-3)18(30-5)17(9-13)29-4/h8-12,14H,6-7H2,1-5H3,(H2,22,23)(H,26,27)/t11-,12+,14+/m0/s1
comment: Compound 31 is a derivative designed to aid the identification of structural elements of the binding pocket of NIMA-related kinase 2 (NEK2) which determine selectivity of inhibitor binding <Reference id=19754/>.
iupac name: (2R,3R,4R)-1-[3-amino-6-(3,4,5-trimethoxyphenyl)pyrazin-2-yl]-2,3-dimethylpiperidine-4-carboxylic acid
xref: CHEMBL1276848
approved: f
ligand name: compound 31 [PMID: 20936789]
type: SyntheticOrganicLigand

PF-03715455
in ch i key: VGEXRDWWPSGZDH-UHFFFAOYSA-N
comment: PF-03715455 (aka compound 1ab) is reported as a potent p38 MAP kinase inhibitor <Reference id=26980/>. The compound was investigated for clinical efficacy as a potential inhalation therapy for chronic obstructive pulmonary disease (COPD).
iupac name: 1-[5-tert-butyl-2-(3-chloro-4-hydroxyphenyl)pyrazol-3-yl]-3-[[2-[[3-[2-(2-hydroxyethylsulfanyl)phenyl]-[1,2,4]triazolo[3,4-f]pyridin-6-yl]sulfanyl]phenyl]methyl]urea
xref: CHEMBL1938400
approved: f
ligand name: PF-03715455
type: SyntheticOrganicLigand

compound 16 [PMID: 18945615]
isomeric SMILES: O=c1[nH]cnc2c1cc([nH]2)c1ccnc(c1)/C=C/c1ccc(cc1)CN1CCOCC1
in ch i key: AWZFCQRICMFIES-AATRIKPKSA-N
in ch i: InChI=1S/C24H23N5O2/c30-24-21-14-22(28-23(21)26-16-27-24)19-7-8-25-20(13-19)6-5-17-1-3-18(4-2-17)15-29-9-11-31-12-10-29/h1-8,13-14,16H,9-12,15H2,(H2,26,27,28,30)/b6-5+
comment: Compound 16 is reported as a potent mitogen-activated protein kinase-activated protein kinase 2 (MK2) inhibitor <Reference id=26979/>.
iupac name: 6-[2-[(E)-2-[4-(morpholin-4-ylmethyl)phenyl]ethenyl]pyridin-4-yl]-1,7-dihydropyrrolo[3,2-e]pyrimidin-4-one
xref: CHEMBL461139
approved: f
ligand name: compound 16 [PMID: 18945615]
type: SyntheticOrganicLigand

compound 16 [PMID: 17480064]
in ch i key: OWFLADWRSCINST-UHFFFAOYSA-N
in ch i: InChI=1S/C21H16N4O/c26-21-16-11-20(25-18(16)6-8-23-21)14-5-7-22-19(10-14)15-9-13-3-1-2-4-17(13)24-12-15/h1-5,7,9-12,25H,6,8H2,(H,23,26)
comment: Compound 16 is reported as a novel, potent and selective inhibitor of mitogen-activated protein kinase-activated protein kinase 2 (MK-2) <Reference id=26977/>.
iupac name: 2-(2-quinolin-3-ylpyridin-4-yl)-1,5,6,7-tetrahydropyrrolo[3,2-c]pyridin-4-one
xref: CHEMBL226403
approved: f
ligand name: compound 16 [PMID: 17480064]
type: SyntheticOrganicLigand

BS-194
in ch i key: KRIWIRSMQRQYJG-DLBZAZTESA-N
in ch i: InChI=1S/C20H27N5O3/c1-13(2)15-10-22-25-19(21-9-14-6-4-3-5-7-14)8-18(24-20(15)25)23-16(11-26)17(28)12-27/h3-8,10,13,16-17,21,26-28H,9,11-12H2,1-2H3,(H,23,24)/t16-,17+/m0/s1
comment: BS-194 is reported as a potent, orally available inhibitor of cyclin-dependent protein kinases (CDKs) 1, 2, 7 and 9 <Reference id=26976/>.
iupac name: (2S,3S)-3-[[7-(benzylamino)-3-propan-2-ylpyrazolo[1,5-a]pyrimidin-5-yl]amino]butane-1,2,4-triol
xref: CHEMBL1234833
synonym: compound 4k [PMID 21080703]
synonym: BS194
synonym: BS 194
approved: f
ligand name: BS-194
type: SyntheticOrganicLigand

compound 1 [PMID: 25408830]
canonical SMILES: NC(=O)c1ccc2c(c1)n(C)c(=O)n2C
isomeric SMILES: NC(=O)c1ccc2c(c1)n(C)c(=O)n2C
in ch i key: BRBLVCVSNVSPMT-UHFFFAOYSA-N
in ch i: InChI=1S/C10H11N3O2/c1-12-7-4-3-6(9(11)14)5-8(7)13(2)10(12)15/h3-5H,1-2H3,(H2,11,14)
comment: The discovery of this compound is described in Demont et al (2014) <Reference id=25994/> DOI: 10.1021/ml5002932.
iupac name: 1,3-dimethyl-2-oxobenzimidazole-5-carboxamide
xref: CHEMBL1487662
synonym: BAS 08314227
approved: f
ligand name: compound 1 [PMID: 25408830]
type: SyntheticOrganicLigand

compound 8h [PMID: 22765894]
in ch i key: XHCPCYVQXFHJAU-UHFFFAOYSA-N
in ch i: InChI=1S/C25H26ClN5O/c1-2-31-13-9-18(10-14-31)29-19-7-8-21-20(15-19)23(25(32)30-21)22(24-27-11-12-28-24)16-3-5-17(26)6-4-16/h3-8,11-12,15,18,29H,2,9-10,13-14H2,1H3,(H,27,28)(H,30,32)
comment: Compound 8h is reported to be a potent inhibitor of several receptor tyrosine kinases, including VEGFRs 1-3, PDGFR, and FGFR1, as well the Src family kinases Src and Yes and the serine threonine kinases MAP4K3 and Rsk2 <Reference id=26973/>.
iupac name: 3-[(4-chlorophenyl)-(1H-imidazol-2-yl)methylidene]-5-[(1-ethylpiperidin-4-yl)amino]-1H-indol-2-one
xref: CHEMBL2086760
approved: f
ligand name: compound 8h [PMID: 22765894]
type: SyntheticOrganicLigand

compound 31 [PMID: 23374866]
canonical SMILES: COCCOc1cnc(nc1c1c[nH]c2c1cc(C#CC(O)(C)C)cc2)N
isomeric SMILES: COCCOc1cnc(nc1c1c[nH]c2c1cc(C#CC(O)(C)C)cc2)N
in ch i key: ZZIZLABGKZWVAW-UHFFFAOYSA-N
in ch i: InChI=1S/C20H22N4O3/c1-20(2,25)7-6-13-4-5-16-14(10-13)15(11-22-16)18-17(27-9-8-26-3)12-23-19(21)24-18/h4-5,10-12,22,25H,8-9H2,1-3H3,(H2,21,23,24)
comment: Compound 31 is reported as an inhibitor of NF-κB-inducing kinase (NIK) discovered using a combination of structure-based design and medicinal chemistry <Reference id=26972/>.
iupac name: 4-[3-[2-amino-5-(2-methoxyethoxy)pyrimidin-4-yl]-1H-indol-5-yl]-2-methylbut-3-yn-2-ol
xref: CHEMBL2334589
approved: f
ligand name: compound 31 [PMID: 23374866]
type: SyntheticOrganicLigand

CEP-1347
in ch i key: SCMLRESZJCKCTC-KMYQRJGFSA-N
in ch i: InChI=1S/C33H33N3O5S2/c1-5-42-15-17-7-9-22-19(11-17)26-27-21(14-34-30(27)37)25-20-12-18(16-43-6-2)8-10-23(20)36-29(25)28(26)35(22)24-13-33(39,31(38)40-4)32(36,3)41-24/h7-12,24,39H,5-6,13-16H2,1-4H3,(H,34,37)/t24-,32+,33+/m1/s1
comment: CEP-1347 is a semi-synthetic analogue of the natural alkaloid <Ligand id=336/> <Reference id=26971/>. CEP-1347 was originally identified as a pan-mixed lineage kinase (MLK) family inhibitor <Reference id=26970/>. In this setting it inhibits downstream c-jun N-terminal kinase (JNK) activation and has neuroprotective activity <Reference id=35247/><Reference id=35248/><Reference id=35249/>.
xref: CHEMBL290352
synonym: KT7515
synonym: KT-7515
synonym: CEP1347
synonym: CEP 1347
approved: f
ligand name: CEP-1347
type: SyntheticOrganicLigand

compound 7 [PMID: 22464456]
in ch i key: CQZZZUNOWZUNNG-UHFFFAOYSA-N
in ch i: InChI=1S/C19H19F2N3OS/c1-3-19(25,4-2)11-6-5-10-7-13(22-12(10)8-11)16-17-14(23-24-16)9-15(26-17)18(20)21/h5-9,18,22,25H,3-4H2,1-2H3,(H,23,24)
comment: Compound 7 is reported as a potent inhibitor of IL2-inducible T-cell kinase (ITK) activity <Reference id=26968/>. This compound was designed using a combination of structure-based design and medicinal chemistry.
iupac name: 3-[(2Z)-2-[5-(difluoromethyl)-1,2-dihydrothieno[3,2-c]pyrazol-3-ylidene]indol-6-yl]pentan-3-ol
xref: CHEMBL2017556
synonym: thienopyrazolylindole inhibitor 477
approved: f
ligand name: compound 7 [PMID: 22464456]
type: SyntheticOrganicLigand

compound 5b [PMID: 24900464]
in ch i key: UZZGMJZTCZOSGC-UHFFFAOYSA-N
in ch i: InChI=1S/C20H17N7O/c1-11(28)24-14-4-5-17-15(6-14)16(10-22-17)18-7-19(25-13-2-3-13)27-20(26-18)12(8-21)9-23-27/h4-7,9-10,13,22,25H,2-3H2,1H3,(H,24,28)
comment: Compound 5b is one of the analogues designed in a medicinal chemistry study to identify inhibitors of casein kinase 2 (CK2) <Reference id=26967/>.
xref: CHEMBL2062581
approved: f
ligand name: compound 5b [PMID: 24900464]
type: SyntheticOrganicLigand

compound 8h [PMID: 21561767]
in ch i key: SUXYGJZMCWKJJI-UHFFFAOYSA-N
in ch i: InChI=1S/C30H33F3N6O3/c1-20-4-5-22(16-21(20)7-9-25-18-35-27(37(25)3)29(42)34-2)28(41)36-24-8-6-23(26(17-24)30(31,32)33)19-39-12-10-38(11-13-39)14-15-40/h4-6,8,16-18,40H,10-15,19H2,1-3H3,(H,34,42)(H,36,41)
comment: Compound 8h is reported as an inhibitor of wild type BCR-Abl and its gatekeeper mutant T315I <Reference id=26965/>.
iupac name: 5-[2-[5-[[4-[[4-(2-hydroxyethyl)piperazin-1-yl]methyl]-3-(trifluoromethyl)phenyl]carbamoyl]-2-methylphenyl]ethynyl]-N,1-dimethylimidazole-2-carboxamide
xref: CHEMBL1784637
approved: f
ligand name: compound 8h [PMID: 21561767]
type: SyntheticOrganicLigand

compound A127 [WO2013110309]
in ch i key: XNAMZBCMLZQBIC-UHFFFAOYSA-N
in ch i: InChI=1S/C20H24N8O2/c1-4-27-10-9-17(25-27)22-19-21-13-16-18(23-19)24-26-28(16)15-7-5-14(6-8-15)20(2,3)30-12-11-29/h5-10,13,29H,4,11-12H2,1-3H3,(H,21,22,23,25)
comment: Compound A127 is an invention covered by patent WO2013110309 <Reference id=26962/>. The compound is reported as an inhibitor of the serine kinase GCN2 (gene symbol EIF2AK4) <Reference id=26963/>, a kinase involved in the regulation of protein synthesis via phosphorylation of the alpha subunit of eukaryotic translation initiation factor-2 (EIF2α) in response to glucose deprivation. The GCN2-EIF2α-ATF4 pathway is essential for maintaining metabolic homeostasis in tumour cells <Reference id=26964/>. Components of this pathway, such as GCN2, are therefore novel targets for the development of anticancer therapeutics.
iupac name: 2-{[2-(4-{5-[(1-ethyl-1H-pyrazol-3-yl)amino]-1H-[1,2,3]triazolo[4,5-d]pyrimidin-1-yl}phenyl)propan-2-yl]oxy}ethan-1-ol
xref: CHEMBL3260333
synonym: A-127
approved: f
ligand name: compound A127 [WO2013110309]
type: SyntheticOrganicLigand

compound 27 [PMID: 19854648]
in ch i key: UUDNGLPFGYJJQX-UHFFFAOYSA-N
comment: Compound 27 is the first reported inhibitor of heme-regulated eukaryotic initiation factor 2α kinase activity (aka HRI; gene symbol EIF2AK1) <Reference id=26961/>.
iupac name: 3-{[(2,6-dichlorophenyl)methyl]amino}-6,7-dimethoxy-1H,4H-indeno[1,2-c]pyrazol-4-one
xref: CHEMBL573760
approved: f
ligand name: compound 27 [PMID: 19854648]
type: SyntheticOrganicLigand

leucettine L41
canonical SMILES: O=C1NC(=NC1=Cc1ccc2c(c1)OCO2)Nc1ccccc1
isomeric SMILES: O=C1NC(=N/C/1=C/c1ccc2c(c1)OCO2)Nc1ccccc1
in ch i key: PGPHHJBZEGSUNE-JYRVWZFOSA-N
in ch i: InChI=1S/C17H13N3O3/c21-16-13(8-11-6-7-14-15(9-11)23-10-22-14)19-17(20-16)18-12-4-2-1-3-5-12/h1-9H,10H2,(H2,18,19,20,21)/b13-8-
comment: Leucettine L41 is a synthetic analogue of the marine sponge derived compound leucettine B <Reference id=26959/>. The leucettines act as inhibitors of two families of serine/threonine kinases; dual-specificity, tyrosine phosphorylation-regulated kinases (DYRKs), and cdc2-like kinases (CLKs), which are involved in Alzheimer’sdisease/Down syndrome and in the control of alternative pre-mRNA splicing.
iupac name: (5Z)-2-anilino-5-(1,3-benzodioxol-5-ylmethylidene)-1H-imidazol-4-one
xref: CHEMBL1802358
approved: f
ligand name: leucettine L41
type: SyntheticOrganicLigand

compound 72 [WO2013026806]
in ch i key: BGXZIBSLBRKDTP-UHFFFAOYSA-N
in ch i: InChI=1S/C17H12ClN5OS/c1-24-15(19)17-23-12-7-6-11-13(14(12)25-17)16(21-8-20-11)22-10-4-2-9(18)3-5-10/h2-8,19H,1H3,(H,20,21,22)
comment: This is compound 72, an invention covered by patent WO2013026806 <Reference id=26956/>. Compound 72 is a highly potent dual DYRK1A/1B inhibitor (DYRK = dual-specificity tyrosine-regulated kinase).
iupac name: methyl 9-(4-chloroanilino)-[1,3]thiazolo[5,4-f]quinazoline-2-carboximidate
xref: CHEMBL2386762
synonym: EHT 5372
synonym: compound 8c [PMID 25264830]
approved: f
ligand name: compound 72 [WO2013026806]
type: SyntheticOrganicLigand

compound 68 [PMID: 24900699]
in ch i key: ZBELDPMWYXDLNY-UHFFFAOYSA-N
comment: Compound 68 is a small molecule reported as a novel, potent inhibitor of the dual-specificity tyrosine-phosphorylation regulated kinases 1A and 1B <Reference id=26951/>.
iupac name: methyl 9-(4-bromo-2-fluoroanilino)-[1,3]thiazolo[5,4-f]quinazoline-2-carboximidate
xref: CHEMBL2386744
approved: f
ligand name: compound 68 [PMID: 24900699]
type: SyntheticOrganicLigand

compound 7k [PMID: 23521020]
canonical SMILES: Clc1cccc(c1)NC(=O)c1ccc(c(c1)C#Cc1cnc2n(c1)ncc2)C
isomeric SMILES: Clc1cccc(c1)NC(=O)c1ccc(c(c1)C#Cc1cnc2n(c1)ncc2)C
in ch i key: PSBGROLQRNSAMY-UHFFFAOYSA-N
in ch i: InChI=1S/C22H15ClN4O/c1-15-5-7-18(22(28)26-20-4-2-3-19(23)12-20)11-17(15)8-6-16-13-24-21-9-10-25-27(21)14-16/h2-5,7,9-14H,1H3,(H,26,28)
comment: Compound 7k is a small molecule identified in a medicinal chemistry study to identify orally available inhibitors of <Reference id=26950/> discoidin domain receptor 1 (DDR1) kinase <Reference id=26950/>.
iupac name: N-(3-chlorophenyl)-4-methyl-3-(2-pyrazolo[1,5-a]pyrimidin-6-ylethynyl)benzamide
xref: CHEMBL2336037
approved: f
ligand name: compound 7k [PMID: 23521020]
type: SyntheticOrganicLigand

compound 33 [PMID: 19364658]
in ch i key: GPXKVULNYYNGDP-UHFFFAOYSA-N
in ch i: InChI=1S/C17H14N4O4/c18-17(25)12(9-2-1-3-11(22)8-9)21-14-13(15(23)16(14)24)20-10-4-6-19-7-5-10/h1-8,12,21-22H,(H2,18,25)(H,19,20)
comment: Compound 33 is a small molecule analogue designed and assessed for inhibitory activity against mitogen activated protein kinase-activated protein kinase 2 (MK2) <Reference id=26949/>.
iupac name: 2-[[3,4-dioxo-2-(pyridin-4-ylamino)cyclobuten-1-yl]amino]-2-(3-hydroxyphenyl)acetamide
xref: CHEMBL511410
approved: f
ligand name: compound 33 [PMID: 19364658]
type: SyntheticOrganicLigand

ML315
in ch i key: JQSJAVBMIMDUFO-UHFFFAOYSA-N
comment: ML315 is a biochemical tool compound identified in the same medicinal chemistry set as <Ligand id=8161/> <Reference id=26948/>, where it is compound 35. ML315 has inhibitory activity against the CLK and DYRK kinase families.
iupac name: 5-(1,3-benzodioxol-5-yl)-N-[(3,5-dichlorophenyl)methyl]pyrimidin-4-amine
xref: CHEMBL1885748
approved: f
ligand name: ML315
type: SyntheticOrganicLigand

compound 17 [PMID: 23642479]
in ch i key: FFJGYBJUQCZAAY-UHFFFAOYSA-N
comment: Compound 17 is one analogue of a medicinal chemistry set designed to identify novel small-molecule inhibitors of the cdc2-like (CLK) and dual specificity tyrosine phosphorylation-regulated (DYRK) kinases <Reference id=26948/>. This set of analogues also includes <Ligand id=8162/>.
iupac name: 4-(1,3-benzodioxol-5-yl)-N-[(3,5-dichlorophenyl)methyl]pyrimidin-2-amine
xref: CHEMBL2392364
approved: f
ligand name: compound 17 [PMID: 23642479]
type: SyntheticOrganicLigand

compound 9b [PMID: 18986805]
in ch i key: OCUYCOQPRGFQEV-UHFFFAOYSA-N
in ch i: InChI=1S/C19H21FN6O/c1-11(2)26-12(3)23-10-17(26)16-7-8-22-19(25-16)24-13-5-6-14(15(20)9-13)18(27)21-4/h5-11H,1-4H3,(H,21,27)(H,22,24,25)
comment: Compound 9b is a potent and selective, orally available cyclin-dependent kinase 2 (CDK2) inhibitor <Reference id=26947/>. Compound 9b is 50-60 times selective for CDK2 compared to CDKs 1 and 4, has potent anti-proliferative activity and favourable pharmacokinetics.
iupac name: 2-fluoro-N-methyl-4-[[4-(2-methyl-3-propan-2-ylimidazol-4-yl)pyrimidin-2-yl]amino]benzamide
xref: CHEMBL455428
approved: f
ligand name: compound 9b [PMID: 18986805]
type: SyntheticOrganicLigand

compound 25 [PMID: 20855207]
in ch i key: QBWKPGNFQQJGFY-QLFBSQMISA-N
in ch i: InChI=1S/C21H26N8OS/c1-12-9-29-18(16-6-23-24-7-16)8-22-21(29)20(25-12)26-19-5-17(27-31-19)15(4)28-10-13(2)30-14(3)11-28/h5-9,13-15H,10-11H2,1-4H3,(H,23,24)(H,25,26)/t13-,14+,15-/m1/s1
comment: Compound 25 is an analogue designed in a medicinal chemistry study to identify novel Aurora kinase inhibitors <Reference id=26946/>. The compound is selective for AuroraA/B versus other tested kinase proteins. It dose-dependently inhibits xenograft tumour growth and has good oral availability in model species <Reference id=26946/>.
iupac name: 3-[(1R)-1-[(2R,6S)-2,6-dimethylmorpholin-4-yl]ethyl]-N-[6-methyl-3-(1H-pyrazol-4-yl)imidazo[1,2-a]pyrazin-8-yl]-1,2-thiazol-5-amine
xref: CHEMBL1270399
approved: f
ligand name: compound 25 [PMID: 20855207]
type: SyntheticOrganicLigand

compound 27 [PMID: 18337095]
in ch i key: UPHCEKNUUNYTFE-UHFFFAOYSA-N
in ch i: InChI=1S/C22H17ClN4O2/c23-13-5-6-17-15(9-13)16(10-25-17)19-20(22(29)26-21(19)28)27-11-12(7-8-24)14-3-1-2-4-18(14)27/h1-6,9-11,25H,7-8,24H2,(H,26,28,29)
comment: Compound 27 is a potent inhibitor of calcium/calmodulin-dependent protein kinase II delta (CAMK2D) reported in <Reference id=26945/>.
iupac name: 3-[3-(2-aminoethyl)-1H-indol-1-yl]-4-(5-chloro-1H-indol-3-yl)-2,5-dihydro-1H-pyrrole-2,5-dione
xref: CHEMBL255607
approved: f
ligand name: compound 27 [PMID: 18337095]
type: SyntheticOrganicLigand

compound 15b [PMID: 18334293]
in ch i key: UGXVRWRXHWTSCU-UHFFFAOYSA-N
in ch i: InChI=1S/C20H20ClN5/c21-16-4-2-5-17(14-16)24-20-23-8-7-19(25-20)15-3-1-6-18(13-15)26-11-9-22-10-12-26/h1-8,13-14,22H,9-12H2,(H,23,24,25)
comment: Compound 15b is a potent inhibitor of calcium/calmodulin-dependent protein kinase II delta (CAMK2D) reported in <Reference id=26944/>.
iupac name: N-(3-chlorophenyl)-4-[3-(piperazin-1-yl)phenyl]pyrimidin-2-amine
xref: CHEMBL270849
synonym: Scios-15b
approved: f
ligand name: compound 15b [PMID: 18334293]
type: SyntheticOrganicLigand

compound 20 [PMID: 22136433]
in ch i key: OWAWOKKHZNRHGV-UHFFFAOYSA-N
in ch i: InChI=1S/C17H16Cl2N4O/c1-23-14-9(2-3-11(18)13(14)19)12-10(8-20)17(4-6-21-7-5-17)22-16(24)15(12)23/h2-3,10,21H,4-7H2,1H3,(H,22,24)
comment: Compound 20 is an analogue developed on a 7,8-dichloro-1-oxo-β-carboline scaffold in a study to identify kinase inhibitors with novel binding modes <Reference id=19652/>.
iupac name: 7',8'-dichloro-9'-methyl-1'-oxo-1',2',4',9'-tetrahydrospiro[piperidine-4,3'-pyrido[3,4-b]indole]-4'-carbonitrile
xref: CHEMBL1945559
approved: f
ligand name: compound 20 [PMID: 22136433]
type: SyntheticOrganicLigand

compound 13a [PMID: 23639540]
in ch i key: WCDLCPLAAKUJNY-UHFFFAOYSA-N
in ch i: InChI=1S/C19H18N6O/c1-3-17(24-5-7-26-8-6-24)4-2-14(1)16-9-20-19-18(12-23-25(19)13-16)15-10-21-22-11-15/h1-4,9-13H,5-8H2,(H,21,22)
comment: The discovery of compound 13a is reported in <Reference id=26903/>, a medicinal chemistry study to identify selective bone morphogenetic protein receptor (BMP) inhibitors. Compound 13a inhibits the majority of Type I receptor serine/threonine kinases to a greater or lesser extent, but is most potent at ALK1 (ACVRL1) and ALK2 (ACVR1) which are activin receptor components, and ALK3 (BMPR1A) and ALK6 (BMPR1B) which are bone morphogenetic protein receptors. Compound 13a has its most potent inhibitory effect on TGFBR2 and VEGFR2, with approximately 25 times lower potency against BMPR2 and AMPK, where reported IC50s are more akin to those at the Type I receptor serine/threonine kinases <Reference id=26903/>.
iupac name: 4-[4-[3-(1H-pyrazol-4-yl)pyrazolo[1,5-a]pyrimidin-6-yl]phenyl]morpholine
xref: CHEMBL2385579
approved: f
ligand name: compound 13a [PMID: 23639540]
type: SyntheticOrganicLigand

compound 14 [PMID: 24900428]
in ch i key: WYOFSHLAFWJJAZ-UHFFFAOYSA-N
in ch i: InChI=1S/C21H20FN3O3/c1-12-7-13(22)3-4-19(12)28-11-14-8-15(20(27-2)10-24-14)18-9-16-17(25-18)5-6-23-21(16)26/h3-4,7-10,25H,5-6,11H2,1-2H3,(H,23,26)
comment: Compound 14 is one of the analogues assessed using structure-based design to identify novel and selective CK1γ Inhibitors <Reference id=24928/>.
iupac name: 2-[2-(4-fluoro-2-methylphenoxymethyl)-5-methoxypyridin-4-yl]-1H,4H,5H,6H,7H-pyrrolo[3,2-c]pyridin-4-one
xref: CHEMBL2203564
approved: f
ligand name: compound 14 [PMID: 24900428]
type: SyntheticOrganicLigand

compound 22m [PMID: 19831390]
in ch i key: BCNLLDVODACBHT-INIZCTEOSA-N
in ch i: InChI=1S/C23H27N9O2/c1-15-11-26-20-19(15)21(29-14-28-20)31-7-8-32(16(2)12-31)23(27-13-24)30-18-5-3-4-17(10-18)22(34)25-6-9-33/h3-5,10-11,14,16,33H,6-9,12H2,1-2H3,(H,25,34)(H,27,30)(H,26,28,29)/t16-/m0/s1
comment: Compound 22m is one of the analogues designed in the search for novel, biologically active LIM domain kinase 2 (LIMK2) inhibitors <Reference id=26940/>.
iupac name: 3-[[(cyanoamino)-[(2S)-2-methyl-4-(5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperazin-1-yl]methylidene]amino]-N-(2-hydroxyethyl)benzamide
xref: CHEMBL571057
approved: f
ligand name: compound 22m [PMID: 19831390]
type: SyntheticOrganicLigand

RKI-1447
canonical SMILES: O=C(Nc1scc(n1)c1ccncc1)NCc1cccc(c1)O
isomeric SMILES: O=C(Nc1scc(n1)c1ccncc1)NCc1cccc(c1)O
in ch i key: GDVRVPIXWXOKQO-UHFFFAOYSA-N
in ch i: InChI=1S/C16H14N4O2S/c21-13-3-1-2-11(8-13)9-18-15(22)20-16-19-14(10-23-16)12-4-6-17-7-5-12/h1-8,10,21H,9H2,(H2,18,19,20,22)
comment: RKI-1447 is a pyridylthiazole-based urea analogue designed in the search for novel and biologically active Rho-associated protein kinase inhibitors <Reference id=26941/>.
iupac name: 1-[(3-hydroxyphenyl)methyl]-3-[4-(pyridin-4-yl)-1,3-thiazol-2-yl]urea
xref: CHEMBL3218011
synonym: RKI1447
synonym: compound 5g [PMID 23275831]
approved: f
ligand name: RKI-1447
type: SyntheticOrganicLigand

compound 14 [PMID: 19831390]
in ch i key: KSECQYDNQYAZMQ-AWEZNQCLSA-N
in ch i: InChI=1S/C20H21BrN8/c1-13-9-23-18-17(13)19(26-12-25-18)28-6-7-29(14(2)10-28)20(24-11-22)27-16-5-3-4-15(21)8-16/h3-5,8-9,12,14H,6-7,10H2,1-2H3,(H,24,27)(H,23,25,26)/t14-/m0/s1
comment: Compound 14 is one of the analogues designed in the search for novel, biologically active LIM domain kinase 2 (LIMK2) inhibitors <Reference id=26940/>.
iupac name: (E,2S)-N-(3-bromophenyl)-N'-cyano-2-methyl-4-{5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl}piperazine-1-carboximidamide
xref: CHEMBL570126
approved: f
ligand name: compound 14 [PMID: 19831390]
type: SyntheticOrganicLigand

GSK579289A
in ch i key: GILNGUYOGYOZMP-MRXNPFEDSA-N
comment: GSK579289A is an anlaogue assessed in a medicinal chemistry study to identify novel thiophene type inhibitors of polo-like kinase 1 (PLK1) <Reference id=26939/>.
iupac name: 3-[(1R)-1-(2-chlorophenyl)ethoxy]-5-[6-(1-methylpiperidin-4-yl)oxybenzimidazol-1-yl]thiophene-2-carboxamide
xref: CHEMBL1794070
synonym: compound 25 [PMID 19237286]
synonym: GSK-579289A
approved: f
ligand name: GSK579289A
type: SyntheticOrganicLigand

compound 2 [PMID: 21627121]
isomeric SMILES: ClCC(=O)c1ccc2c(c1)/C(=C/c1ccc[nH]1)/C(=O)N2
in ch i key: SEPHEVMRHYRRLS-GHXNOFRVSA-N
in ch i: InChI=1S/C15H11ClN2O2/c16-8-14(19)9-3-4-13-11(6-9)12(15(20)18-13)7-10-2-1-5-17-10/h1-7,17H,8H2,(H,18,20)/b12-7-
comment: Compound 2 is an analogue tested in a medicinal chemistry study to identify novel, irreversible inhibitors of NIMA-related kinase 2 (Nek2), a centrosome-associated serine/threonine kinase with a role in kinesin-5-driven bipolar spindle assembly <Reference id=26938/>.
iupac name: (3Z)-5-(2-chloroacetyl)-3-(1H-pyrrol-2-ylmethylidene)-1H-indol-2-one
xref: CHEMBL1802381
approved: f
ligand name: compound 2 [PMID: 21627121]
type: SyntheticOrganicLigand

compound 31 [PMID: 24915291]
in ch i key: BTWVWABAWDKQNJ-UHFFFAOYSA-N
in ch i: InChI=1S/C29H23F3N6O3/c1-3-25(39)35-20-8-5-9-21(13-20)38-28-33-15-23(16-34-28)37-27(41)24-14-22(11-10-17(24)2)36-26(40)18-6-4-7-19(12-18)29(30,31)32/h3-16H,1H2,2H3,(H,35,39)(H,36,40)(H,37,41)(H,33,34,38)
comment: Compound 31 is a novel 2,5-diaminopyrimidin based analogue repoted as an irreversible inhibitor of Bruton’s tyrosine kinase (Btk) <Reference id=26933/>. The selectivity profile of this compound differs from that of <Ligand id=6912/>, the first irreversible Btk inhibitor discovered.
iupac name: 2-methyl-N-(2-{[3-(prop-2-enamido)phenyl]amino}pyrimidin-5-yl)-5-[3-(trifluoromethyl)benzamido]benzamide
xref: CHEMBL3290142
approved: f
ligand name: compound 31 [PMID: 24915291]
type: SyntheticOrganicLigand

compound 24 [PMID: 23441572]
in ch i key: VSJSIOZQNZPUAV-UHFFFAOYSA-N
in ch i: InChI=1S/C29H27F3N6O/c1-20-3-4-22(15-21(20)6-8-25-17-33-18-27-34-9-10-38(25)27)28(39)35-24-7-5-23(26(16-24)29(30,31)32)19-37-13-11-36(2)12-14-37/h3-5,7,9-10,15-18H,11-14,19H2,1-2H3,(H,35,39)
comment: Compound 24 targets wild yype and mutant Abl kinases <Reference id=26935/>.
iupac name: 3-(2-imidazo[1,2-a]pyrazin-5-ylethynyl)-4-methyl-N-[4-[(4-methylpiperazin-1-yl)methyl]-3-(trifluoromethyl)phenyl]benzamide
xref: CHEMBL2324924
approved: f
ligand name: compound 24 [PMID: 23441572]
type: SyntheticOrganicLigand

compound 23 [PMID: 17600705]
in ch i key: LKLIRPMEYRVLFV-UHFFFAOYSA-N
in ch i: InChI=1S/C17H17N5O3S/c1-11-5-6-13(23)10-15(11)21-16-7-8-19-17(22-16)20-12-3-2-4-14(9-12)26(18,24)25/h2-10,23H,1H3,(H2,18,24,25)(H2,19,20,21,22)
comment: Compound 23 is one of the analogues assessed in a study to find novel inhibitors of LCK proto-oncogene (Lck) kinase activity <Reference id=26934/>.
iupac name: 3-[[4-(5-hydroxy-2-methylanilino)pyrimidin-2-yl]amino]benzenesulfonamide
xref: CHEMBL249317
approved: f
ligand name: compound 23 [PMID: 17600705]
type: SyntheticOrganicLigand

compound 38 [PMID: 24915291]
in ch i key: SMOPKEHQPPXRSH-UHFFFAOYSA-N
in ch i: InChI=1S/C31H26F3N7O4/c1-3-26(42)35-17-27(43)38-21-8-5-9-22(13-21)41-30-36-15-24(16-37-30)40-29(45)25-14-23(11-10-18(25)2)39-28(44)19-6-4-7-20(12-19)31(32,33)34/h3-16H,1,17H2,2H3,(H,35,42)(H,38,43)(H,39,44)(H,40,45)(H,36,37,41)
comment: Compound 38 is an analogue assessed in a study to design covalent irreversible inhibitors of Bruton's tyrosine kinase (Btk) <Reference id=26933/>.
xref: CHEMBL3290148
approved: f
ligand name: compound 38 [PMID: 24915291]
type: SyntheticOrganicLigand

compound 1o [PMID: 24210504]
in ch i key: MWVKLRSIDOXBSE-UHFFFAOYSA-N
in ch i: InChI=1S/C24H27N7O/c25-23-20(24-29-21-4-3-19(12-22(21)32-24)30-9-1-2-10-30)11-16(13-27-23)17-14-28-31(15-17)18-5-7-26-8-6-18/h3-4,11-15,18,26H,1-2,5-10H2,(H2,25,27)
comment: Compound 1o was designed and tested in a study to identify selective inhibitors of G protein-coupled receptor kinases, GRK2 and GRK5 <Reference id=26931/>.
iupac name: 5-(1-piperidin-4-ylpyrazol-4-yl)-3-(6-pyrrolidin-1-yl-1,3-benzoxazol-2-yl)pyridin-2-amine
xref: CHEMBL3093151
approved: f
ligand name: compound 1o [PMID: 24210504]
type: SyntheticOrganicLigand

balanol
in ch i key: XYUFCXJZFZPEJD-XMSQKQJNSA-N
in ch i: InChI=1S/C28H26N2O10/c31-16-8-6-14(7-9-16)26(36)30-18-13-29-10-2-5-22(18)40-28(39)15-11-20(33)24(21(34)12-15)25(35)23-17(27(37)38)3-1-4-19(23)32/h1,3-4,6-9,11-12,18,22,29,31-34H,2,5,10,13H2,(H,30,36)(H,37,38)/t18-,22-/m1/s1
comment: Balanol is a fungal metabolite which acts as a non-selective ATP-competitive inhibitor of protein kinases A, G and C (AGC family kinases) <Reference id=26927/><Reference id=26926/><Reference id=26930/>. Balanol is also reported to inhibit G protein-coupled receptor kinases (GRKs), with modest selectivity for the GRK2 family members, GRK2 and GRK3 <Reference id=26928/>.
iupac name: 2-[2,6-dihydroxy-4-[(3R,4R)-3-[(4-hydroxybenzoyl)amino]azepan-4-yl]oxycarbonylbenzoyl]-3-hydroxybenzoic acid
xref: CHEMBL60254
synonym: azepinostatin
approved: f
ligand name: balanol
type: NaturalProductLigand

compound 66 [PMID: 19788238]
in ch i key: JTWMOWRMSZZHDR-UHFFFAOYSA-N
in ch i: InChI=1S/C22H19N5O4/c1-12-8-9-13(28)10-14(12)16-11-26-18-19(25(2)22(30)24-20(18)29)23-21(26)27(16)15-6-4-5-7-17(15)31-3/h4-11,28H,1-3H3,(H,24,29,30)
comment: Compound 66 is reported as a potent ephrin receptor inhibitor designed as part of a structure-based optimisation study <Reference id=26925/>. Compound 66 inhibits all ephrin receptors except EphA7 (1118nM) with low nanomolar IC50s (1-40nM) <Reference id=26925/>. Modelling suggests that EphA7 is an outlier as it has a bulky isoleucine residue at its gatekeeper position, compared to a smaller threonine in this position in all of the other ephrin receptors<Reference id=26925/>.
iupac name: 7-(5-hydroxy-2-methylphenyl)-6-(2-methoxyphenyl)-4-methylpurino[7,8-a]imidazole-1,3-dione
xref: CHEMBL566515
approved: f
ligand name: compound 66 [PMID: 19788238]
type: SyntheticOrganicLigand

compound 2c [PMID: 22115617]
in ch i key: PHAOTASRLQMKBE-UHFFFAOYSA-N
in ch i: InChI=1S/C11H9Br4N3O2/c1-17(2)11-16-9-7(14)5(12)6(13)8(15)10(9)18(11)3-4(19)20/h3H2,1-2H3,(H,19,20)
comment: Compound 2c is a potent inhibitor of the alpha prime (α'; gene symbol CSNK2A2) subunit of casein kinase 2 (CK2) <Reference id=26924/>. The compound is four times more potent at CK2α' compared to CK2α as assessed by subunit-induced inhibition of phosphorylation of a synthetic peptide substrate <Reference id=26924/>.
iupac name: 2-[4,5,6,7-tetrabromo-2-(dimethylamino)benzimidazol-1-yl]acetic acid
xref: CHEMBL1233807
approved: f
ligand name: compound 2c [PMID: 22115617]
type: SyntheticOrganicLigand

compound 25b [PMID: 22564207]
in ch i key: LAJAFFLJAJMYLK-CVOKMOJFSA-N
in ch i: InChI=1S/C28H35ClN6O3/c1-37-25-20-8-7-19(35-10-12-38-13-11-35)6-4-16(20)5-9-22(25)32-28-31-15-21(29)27(34-28)33-24-18-3-2-17(14-18)23(24)26(30)36/h2-3,5,9,15,17-19,23-24H,4,6-8,10-14H2,1H3,(H2,30,36)(H2,31,32,33,34)/t17-,18+,19+,23+,24-/m1/s1
comment: Compound 25b is a potent and selective, orally available inhibitor of anaplastic lymphoma receptor tyrosine kinase (ALK) <Reference id=26923/>.
iupac name: (1S,2S,3R,4R)-3-[(5-Chloro-2-{[(7S)-1-methoxy-7-(4-morpholinyl)-6,7,8,9-tetrahydro-5H-benzo[7]annulen-2-yl]amino}-4-pyrimidinyl)amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide
xref: CHEMBL2064666
approved: f
ligand name: compound 25b [PMID: 22564207]
type: SyntheticOrganicLigand

compound 2c [PMID: 24900538]
in ch i key: FZBVNCFBCNXULH-LBPRGKRZSA-N
in ch i: InChI=1S/C19H20FN7O/c1-11(2)28-18-8-17(25-26-18)27-10-22-15-6-7-16(24-19(15)27)23-12(3)14-5-4-13(20)9-21-14/h4-12H,1-3H3,(H,23,24)(H,25,26)/t12-/m0/s1
comment: Compound 2c is one of the analogues identified by a medicinal chemistry approach to identify neurotrophic tyrosine kinase, receptor, type 1 (TrkA) inhibitors <Reference id=26922/>.
iupac name: N-[(1S)-1-(5-fluoropyridin-2-yl)ethyl]-3-(3-propan-2-yloxy-1H-pyrazol-5-yl)imidazo[4,5-b]pyridin-5-amine
xref: CHEMBL2151321
approved: f
ligand name: compound 2c [PMID: 24900538]
type: SyntheticOrganicLigand

compound 8e [PMID: 24432909]
in ch i key: DIXMBHMNEHPFCX-MCMMXHMISA-N
in ch i: InChI=1S/C22H23FN6O3S/c1-12-19(33-21(28-12)22(3,31)11-30)14-8-18(20(24)25-10-14)32-13(2)16-9-15(23)4-5-17(16)29-26-6-7-27-29/h4-10,13,30-31H,11H2,1-3H3,(H2,24,25)/t13-,22-/m1/s1
comment: Compound 8e it was tested in a medicinal chemistry study to identify small molecule inhibitors of mutated anaplastic lymphoma kinase (Alk) which confer crizotinib resistance <Reference id=24318/>.
iupac name: (2R)-2-[5-[6-amino-5-[(1R)-1-[5-fluoro-2-(triazol-2-yl)phenyl]ethoxy]pyridin-3-yl]-4-methyl-1,3-thiazol-2-yl]propane-1,2-diol
xref: CHEMBL3128069
approved: f
ligand name: compound 8e [PMID: 24432909]
type: SyntheticOrganicLigand

compound 2 [PMID: 15546730]
in ch i key: WFRLFWGASBLYTC-UHFFFAOYSA-N
in ch i: InChI=1S/C17H16ClN5OS/c1-9-5-4-6-12(18)15(9)23-16(24)13-8-19-17(25-13)22-14-7-10(2)20-11(3)21-14/h4-8H,1-3H3,(H,23,24)(H,19,20,21,22)
comment: Compound 2 is representative analog developed in a medicinal chemistry study to optimise inhibition of LCK proto-oncogene, Src family tyrosine kinase (Lck) <Reference id=26919/>.
iupac name: N-(2-chloro-6-methylphenyl)-2-[(2,6-dimethylpyrimidin-4-yl)amino]-1,3-thiazole-5-carboxamide
xref: CHEMBL364623
approved: f
ligand name: compound 2 [PMID: 15546730]
type: SyntheticOrganicLigand

compound 21 [PMID: 23312943]
in ch i key: ZTSOUDMNSOYCTG-UHFFFAOYSA-N
in ch i: InChI=1S/C22H26Cl2N6O/c1-13-8-20(31-29-13)19-12-25-22(27-17-10-14(23)9-15(24)11-17)28-21(19)26-16-4-6-18(7-5-16)30(2)3/h8-12,16,18H,4-7H2,1-3H3,(H2,25,26,27,28)
comment: Compound 21 is a potent inhibitor of TYRO3 protein tyrosine kinase (Sky kinase) <Reference id=26918/>. It is suitable as an in vitro and in vivo tool to probe the effects of Sky inhibition.
iupac name: 2-N-(3,5-dichlorophenyl)-4-N-[4-(dimethylamino)cyclohexyl]-5-(3-methyl-1,2-oxazol-5-yl)pyrimidine-2,4-diamine
xref: CHEMBL2312654
approved: f
ligand name: compound 21 [PMID: 23312943]
type: SyntheticOrganicLigand

compound 26 [PMID: 24673130]
canonical SMILES: Fc1cccc(c1)c1ccc2c(n1)c(N)ncn2
isomeric SMILES: Fc1cccc(c1)c1ccc2c(n1)c(N)ncn2
in ch i key: TWTLUQDFSDYZKO-UHFFFAOYSA-N
in ch i: InChI=1S/C13H9FN4/c14-9-3-1-2-8(6-9)10-4-5-11-12(18-10)13(15)17-7-16-11/h1-7H,(H2,15,16,17)
comment: Compound 26 is a selective inhibitor of MAP4K4 (mitogen-activated protein kinase kinase kinase kinase 4) <Reference id=26917/>.
iupac name: 6-(3-fluorophenyl)pyrido[3,2-d]pyrimidin-4-amine
xref: CHEMBL3262587
approved: f
ligand name: compound 26 [PMID: 24673130]
type: SyntheticOrganicLigand

compound 10 [PMID: 23147077]
in ch i key: SMJAMOAYGIVKRI-UHFFFAOYSA-N
in ch i: InChI=1S/C21H21N5O/c1-21(2,3)16-6-4-15(5-7-16)20(27)24-18-13-26-12-17(8-9-19(26)23-18)25-11-10-22-14-25/h4-14H,1-3H3,(H,24,27)
comment: Compound 10 is an ASK1 (apoptosis signal-regulating kinase 1) inhibitor <Reference id=24926/>, with approximately 50 fold selectivity compared to ASK2 (aka MEKK6 or MAP3K6).
iupac name: 4-tert-butyl-N-(6-imidazol-1-ylimidazo[1,2-a]pyridin-2-yl)benzamide
xref: CHEMBL1642655
synonym: TC ASK 10
approved: f
ligand name: compound 10 [PMID: 23147077]
type: SyntheticOrganicLigand

Il-94
in ch i key: FTGUWURNNBVUBC-UHFFFAOYSA-N
in ch i: InChI=1S/C21H23FN8O/c1-31-7-6-30(12-14-8-15(22)9-18-16(14)11-24-27-18)21-23-5-4-19(26-21)25-20-10-17(28-29-20)13-2-3-13/h4-5,8-11,13H,2-3,6-7,12H2,1H3,(H,24,27)(H2,23,25,26,28,29)
comment: Il-94 is a PAK1 (p21 protein (Cdc42/Rac)-activated kinase 1) inhibitor <Reference id=26916/>.
iupac name: 4-N-(5-cyclopropyl-1H-pyrazol-3-yl)-2-N-[(6-fluoro-1H-indazol-4-yl)methyl]-2-N-(2-methoxyethyl)pyrimidine-2,4-diamine
xref: CHEMBL2386715
approved: f
ligand name: Il-94
type: SyntheticOrganicLigand

compound 24 [PMID: 15955699]
canonical SMILES: CCn1c(nc2c1c(CN1CCNCC1)cnc2)c1nonc1N
isomeric SMILES: CCn1c(nc2c1c(CN1CCNCC1)cnc2)c1nonc1N
in ch i key: OXZLPOLYTISTQY-UHFFFAOYSA-N
in ch i: InChI=1S/C15H20N8O/c1-2-23-13-10(9-22-5-3-17-4-6-22)7-18-8-11(13)19-15(23)12-14(16)21-24-20-12/h7-8,17H,2-6,9H2,1H3,(H2,16,21)
comment: Compound 24 is a potent inhibitor of ribosomal protein S6 kinase, polypeptide 5 (RPS6KA5), also known as MSK1 <Reference id=26915/>. This compound has selectivity over glycogen synthase 3 (GSK3) and ribosomal protein S6 kinase, polypeptide 1 (aka RSK1).
iupac name: 4-[1-ethyl-7-(piperazin-1-ylmethyl)imidazo[4,5-c]pyridin-2-yl]-1,2,5-oxadiazol-3-amine
xref: CHEMBL415770
approved: f
ligand name: compound 24 [PMID: 15955699]
type: SyntheticOrganicLigand

SB-747651A
canonical SMILES: CCn1c(nc2c1c(CNC1CCNCC1)cnc2)c1nonc1N
isomeric SMILES: CCn1c(nc2c1c(CNC1CCNCC1)cnc2)c1nonc1N
in ch i key: MBCJUIJWPYUEBX-UHFFFAOYSA-N
in ch i: InChI=1S/C16H22N8O/c1-2-24-14-10(8-20-11-3-5-18-6-4-11)7-19-9-12(14)21-16(24)13-15(17)23-25-22-13/h7,9,11,18,20H,2-6,8H2,1H3,(H2,17,23)
comment: SB-747651A is a potent inhibitor of ribosomal protein S6 kinase, polypeptide 5 (RPS6KA5), also known as MSK1 <Reference id=26915/>. This compound has selectivity over glycogen synthase 3 (GSK3) and ribosomal protein S6 kinase, polypeptide 1 (aka RSK1).
iupac name: N-[[2-(4-amino-1,2,5-oxadiazol-3-yl)-1-ethylimidazo[5,4-d]pyridin-7-yl]methyl]piperidin-4-amine
xref: CHEMBL188434
synonym: compound 26
approved: f
ligand name: SB-747651A
type: SyntheticOrganicLigand

compound 34 [PMID: 24749861]
canonical SMILES: O=Cc1c(O)ccc2c1oc(=O)c1c2CCN(C1)C(=N)N
isomeric SMILES: O=Cc1c(O)ccc2c1oc(=O)c1c2CCN(C1)C(=N)N
in ch i key: YPBDMIVAGFLWPR-UHFFFAOYSA-N
in ch i: InChI=1S/C14H13N3O4/c15-14(16)17-4-3-7-8-1-2-11(19)10(6-18)12(8)21-13(20)9(7)5-17/h1-2,6,19H,3-5H2,(H3,15,16)
comment: Compound 34 is a potent inhibitor of the protein kinase ERN1 (endoplasmic reticulum to nucleus signaling 1) <Reference id=26914/>. ERN1 is also known as IRE1, and is an endoplasmic reticulum stress sensor which signals to the nucleus in response to abnormal levels of unfolded proteins. Compound 34 inhibits the RNAse domain of the protein, like other salicylaldehyde-containing molecules.
iupac name: 7-formyl-8-hydroxy-5-oxo-1H,2H,3H,4H,5H-chromeno[3,4-c]pyridine-3-carboximidamide
xref: CHEMBL3265274
approved: f
ligand name: compound 34 [PMID: 24749861]
type: SyntheticOrganicLigand

compound 1a [PMID: 24900749]
in ch i key: GDSQVLMYYCNAGP-UHFFFAOYSA-N
in ch i: InChI=1S/C19H19N7O/c1-11-3-4-15(7-16(11)22-12(2)27)23-17-8-18(24-14-5-6-14)26-19(25-17)13(9-20)10-21-26/h3-4,7-8,10,14,24H,5-6H2,1-2H3,(H,22,27)(H,23,25)
comment: Compound 1a was developed as a casein kinase 2 (CK2) inhibitor <Reference id=26913/>.
iupac name: N-[5-[[3-cyano-7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidin-5-yl]amino]-2-methylphenyl]acetamide
xref: CHEMBL2409175
approved: f
ligand name: compound 1a [PMID: 24900749]
type: SyntheticOrganicLigand

compound 3b [PMID: 23454515]
in ch i key: ZBYBDKHFLSHGBP-QNGOZBTKSA-N
in ch i: InChI=1S/C25H30N4O7/c26-7-8-31-9-10-32-11-12-33-13-14-34-20-4-2-19(3-5-20)27-25-28-21(24(30)29-25)15-18-1-6-22-23(16-18)36-17-35-22/h1-6,15-16H,7-14,17,26H2,(H2,27,28,29,30)/b21-15-
comment: Compound 3b is a derivative of the marine sponge extract Leucettine L41 <Reference id=26912/>. The modification adds four amino-polyethylene glycol linkers to facilitate immobilisation of the compound for screening assays. Leucettines are potent inhibitors of DYRKs (dual-specificity, tyrosine phosphorylation regulated kinases) and CLKs (cdc2-like kinases).
xref: CHEMBL3092863
approved: f
ligand name: compound 3b [PMID: 23454515]
type: SyntheticOrganicLigand

silmitasertib
in ch i key: MUOKSQABCJCOPU-UHFFFAOYSA-N
in ch i: InChI=1S/C19H12ClN3O2/c20-12-2-1-3-13(9-12)22-18-15-6-7-21-10-16(15)14-5-4-11(19(24)25)8-17(14)23-18/h1-10H,(H,22,23)(H,24,25)
comment: Silmitasertib (CX-4945) is a a potent and selective inhibitor of CK2 (casein kinase 2) <Reference id=26910/><Reference id=26911/>. CX-4945 is described in the same article as <Ligand id=9373/> and <Ligand id=9374/> <Reference id=31819/>. SARS-CoV-2 Silmitasertib, via inhibition of CK2, was found to produce an in vitro antiviral effect (IC50 = 2.34 μM;) <Reference id=39830/>. In conjunction with data supporting a physical interaction <Reference id=38977/> and co-localization of CK2 with SARS-CoV-2 N protein, and evidence of potential role of CK2 in remodeling extracellular matrix upon infection <Reference id=39830/>, it can be hypothesised that the CK2 pathway is hijacked by SARS-CoV-2. Thus, it makes pharmacological sense that silmitasertib should be considered for investigation as an anti-SARS-CoV-2 therapeutic.
iupac name: 5-[(3-chlorophenyl)amino]pyrido[4,3-c]quinoline-8-carboxylic acid
xref: CHEMBL1230165
synonym: CX-4945
synonym: CX4945
synonym: CX 4945
approved: f
ligand name: silmitasertib
type: SyntheticOrganicLigand

THI
canonical SMILES: CC(=O)c1nc(c[nH]1)C(C(C(CO)O)O)O
in ch i key: CQSIXFHVGKMLGQ-BWZBUEFSSA-N
in ch i: InChI=1S/C9H14N2O5/c1-4(13)9-10-2-5(11-9)7(15)8(16)6(14)3-12/h2,6-8,12,14-16H,3H2,1H3,(H,10,11)/t6-,7-,8-/m1/s1
iupac name: 1-[4-[(1R,2S,3R)-1,2,3,4-tetrahydroxybutyl]-3H-imidazol-2-yl]ethanone
xref: CHEMBL488336
synonym: 2-acetyl-5-tetrahydroxybutyl imidazole
approved: f
ligand name: THI
type: SyntheticOrganicLigand

compound 12 [PMID: 22521646]
in ch i key: REGFSKAVJRCHTE-UHFFFAOYSA-N
in ch i: InChI=1S/C21H21FN4O/c1-12-16(9-14(10-17(12)22)19(27)23-15-3-4-15)13-5-8-26-18(11-13)24-25-20(26)21(2)6-7-21/h5,8-11,15H,3-4,6-7H2,1-2H3,(H,23,27)
comment: Compound 12 is a p38α (MAPK14) inhibitor <Reference id=26909/>.
iupac name: N-cyclopropyl-3-fluoro-4-methyl-5-[3-(1-methylcyclopropyl)-[1,2,4]triazolo[4,3-a]pyridin-7-yl]benzamide
xref: CHEMBL2087507
approved: f
ligand name: compound 12 [PMID: 22521646]
type: SyntheticOrganicLigand

compound 20 [PMID: 23489211]
in ch i key: ITOFPJRDSCGOSA-KZLRUDJFSA-N
in ch i: InChI=1S/C35H50N2O4/c1-21(8-13-32(39)37-31(33(40)41)18-22-20-36-30-7-5-4-6-25(22)30)27-11-12-28-26-10-9-23-19-24(38)14-16-34(23,2)29(26)15-17-35(27,28)3/h4-7,20-21,23-24,26-29,31,36,38H,8-19H2,1-3H3,(H,37,39)(H,40,41)/t21-,23-,24-,26+,27-,28+,29+,31+,34+,35-/m1/s1
comment: Compound 20 is a L-tryptophan conjugate of lithocholic acid. It was developed as a non-peptide pharmacological tool for the study of ephrin (Eph) receptor activity. Compound 20 inhibits all ephrin (Eph) receptors tested, with a slight EphA preference <Reference id=26908/>. This suggests a common binding site across the EphA and EphB receptor families <Reference id=26908/>.
iupac name: (2S)-2-[[(4R)-4-[(3R,5R,8R,9S,10S,13R,14S,17R)-3-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoyl]amino]-3-(1H-indol-3-yl)propanoic acid
xref: CHEMBL2322989
synonym: PCM126
approved: f
ligand name: compound 20 [PMID: 23489211]
type: SyntheticOrganicLigand

compound 1d [PMID: 21493067]
in ch i key: HIHOEGPXVVKJPP-JTQLQIEISA-N
in ch i: InChI=1S/C17H15F2N7/c1-9-5-15(26-25-9)23-17-13(19)6-11(7-20)16(24-17)22-10(2)14-4-3-12(18)8-21-14/h3-6,8,10H,1-2H3,(H3,22,23,24,25,26)/t10-/m0/s1
comment: Compound 1d is a moderately selective JAK2 inhibitor <Reference id=26907/>.
iupac name: 5-fluoro-2-{[1-(5-fluoropyridin-2-yl)ethyl]amino}-6-[(5-methyl-1H-pyrazol-3-yl)amino]pyridine-3-carbonitrile
xref: CHEMBL1774056
approved: f
ligand name: compound 1d [PMID: 21493067]
type: SyntheticOrganicLigand

compound 25 [PMID: 17935989]
in ch i key: AZTMYWWWILJAKW-UHFFFAOYSA-N
comment: Compound 25 is a checkpoint kinase 1 (CHK1) inhibitor. Its discovery is reported in <Reference id=26906/> and this article provides screening results across a large kinase panel.
xref: CHEMBL248757
approved: f
ligand name: compound 25 [PMID: 17935989]
type: SyntheticOrganicLigand

ML347
in ch i key: FVRYPYDPKSZGNS-UHFFFAOYSA-N
in ch i: InChI=1S/C22H16N4O/c1-27-17-9-7-15(8-10-17)16-12-24-22-20(13-25-26(22)14-16)18-4-2-6-21-19(18)5-3-11-23-21/h2-14H,1H3
comment: ML347 is a selective inhibitor of ALK2 (activin A receptor, type I, ACVR1) compared to ALK3 (bone morphogenetic protein receptor, type IA , BMPR1A) <Reference id=26903/>.
iupac name: 5-[6-(4-methoxyphenyl)pyrazolo[1,5-a]pyrimidin-3-yl]quinoline
xref: CHEMBL502351
synonym: ML-347
approved: f
ligand name: ML347
type: SyntheticOrganicLigand

compound 13d [PMID: 23639540]
in ch i key: SZVLDZCYMADNPG-UHFFFAOYSA-N
in ch i: InChI=1S/C25H21N5O/c1-2-4-24-22(3-1)21(9-10-26-24)23-16-28-30-17-19(15-27-25(23)30)18-5-7-20(8-6-18)29-11-13-31-14-12-29/h1-10,15-17H,11-14H2
comment: The discovery of compound 13d is reported in <Reference id=26903/>, a medicinal chemistry study to identify selective bone morphogenetic protein receptor (BMP) inhibitors. Compound 13d inhibits all of the Type I receptor serine/threonine kinases to a greater or lesser extent, but is most potent at ALK1 (ACVRL1) and ALK2 (ACVR1) which are activin receptor components, and ALK3 (BMPR1A) and ALK6 (BMPR1B) which are bone morphogenetic protein receptors.
iupac name: 4-[4-(3-quinolin-4-ylpyrazolo[1,5-a]pyrimidin-6-yl)phenyl]morpholine
xref: CHEMBL2385582
approved: f
ligand name: compound 13d [PMID: 23639540]
type: SyntheticOrganicLigand

compound 35 [PMID: 22902653]
in ch i key: XACSASLXEAYEEO-UHFFFAOYSA-N
comment: Compound 35 was designed as an inhibitor of the LIM domain kinases LIMK1 and LIMK2 <Reference id=26897/>. Compound 35 exhibits selectivity for the LIMs over the testis-specific protein kinases (TESKs) <Reference id=26897/>.
iupac name: N-[5-[6-(2,6-dichloro-4-methoxyphenyl)-2-pyrazin-2-ylpyrimidin-4-yl]-1,3-thiazol-2-yl]acetamide
xref: CHEMBL2070619
approved: f
ligand name: compound 35 [PMID: 22902653]
type: SyntheticOrganicLigand

D-glucosamine
canonical SMILES: OCC1OC(O)C(C(C1O)O)N
in ch i key: MSWZFWKMSRAUBD-QZABAPFNSA-N
in ch i: InChI=1S/C6H13NO5/c7-3-5(10)4(9)2(1-8)12-6(3)11/h2-6,8-11H,1,7H2/t2-,3-,4-,5-,6-/m1/s1
iupac name: (2R,3R,4R,5S,6R)-3-amino-6-(hydroxymethyl)oxane-2,4,5-triol
xref: CHEMBL234432
approved: f
ligand name: D-glucosamine
type: MetaboliteLigand

compound 30 [PMID: 22902653]
in ch i key: RYXLLTGGHCFCFK-UHFFFAOYSA-N
in ch i: InChI=1S/C26H29N7O2S/c1-6-17(7-2)35-18-10-15(3)23(16(4)11-18)20-12-19(22-14-30-26(36-22)33-25(34)27-5)31-24(32-20)21-13-28-8-9-29-21/h8-14,17H,6-7H2,1-5H3,(H2,27,30,33,34)
comment: Compound 30 was designed as an inhibitor of the LIM domain kinases LIMK1 and LIMK2 <Reference id=26897/>
iupac name: 1-[5-[6-(2,6-dimethyl-4-pentan-3-yloxyphenyl)-2-pyrazin-2-ylpyrimidin-4-yl]-1,3-thiazol-2-yl]-3-methylurea
xref: CHEMBL2070613
approved: f
ligand name: compound 30 [PMID: 22902653]
type: SyntheticOrganicLigand

compound 31 [PMID: 22902653]
in ch i key: WUCYRTXFXRZKSV-UHFFFAOYSA-N
in ch i: InChI=1S/C23H23N7O2S/c1-5-25-22(31)30-23-27-12-19(33-23)16-10-17(20-13(2)8-15(32-4)9-14(20)3)29-21(28-16)18-11-24-6-7-26-18/h6-12H,5H2,1-4H3,(H2,25,27,30,31)
comment: Compound 31 was designed as an inhibitor of the LIM domain kinases LIMK1 and LIMK2 <Reference id=26897/>.
xref: CHEMBL2070615
approved: f
ligand name: compound 31 [PMID: 22902653]
type: SyntheticOrganicLigand

compound 22 [PMID: 21823616]
in ch i key: GHBUPSVATJKTRR-UHFFFAOYSA-N
in ch i: InChI=1S/C30H30F3N5O/c1-34-29(39)15-10-25-20-28(38(36-25)27-13-11-26(12-14-27)37-18-16-35-17-19-37)23-4-2-21(3-5-23)22-6-8-24(9-7-22)30(31,32)33/h2-9,11-14,20,35H,10,15-19H2,1H3,(H,34,39)
comment: Compound 22 was a lead reported as the result of a compound screen for inhibitors of the protein kinase integrin-linked kinase (ILK) <Reference id=26883/>.
iupac name: N-methyl-3-[1-(4-piperazin-1-ylphenyl)-5-[4-[4-(trifluoromethyl)phenyl]phenyl]pyrazol-3-yl]propanamide
xref: CHEMBL1830587
approved: f
ligand name: compound 22 [PMID: 21823616]
type: SyntheticOrganicLigand

compound 2 [PMID: 22560567]
canonical SMILES: Oc1ccc(cc1C)c1nc(=O)[nH]c(c1)c1ccccc1
isomeric SMILES: Oc1ccc(cc1C)c1nc(=O)[nH]c(c1)c1ccccc1
in ch i key: MHPMAOLCNNEBOA-UHFFFAOYSA-N
in ch i: InChI=1S/C17H14N2O2/c1-11-9-13(7-8-16(11)20)15-10-14(18-17(21)19-15)12-5-3-2-4-6-12/h2-10,20H,1H3,(H,18,19,21)
comment: Compound 2 was originally reported as a PIM1 kinase inhibitor, and was used as a scaffold for the design of CDC7 inhibitors described in <Reference id=26881/>. PubChem CID 6747541 represents an alternative tautomer of this chemical structure.
iupac name: 4-(4-hydroxy-3-methylphenyl)-6-phenyl-1,2-dihydropyrimidin-2-one
xref: CHEMBL501724
approved: f
ligand name: compound 2 [PMID: 22560567]
type: SyntheticOrganicLigand

compound 89S [PMID: 19115845]
canonical SMILES: FCCC1CNC(=O)c2c1[nH]c(c2)c1ccnc(n1)N
in ch i key: LCBAQTCTQXHTJG-ZETCQYMHSA-N
in ch i: InChI=1S/C13H14FN5O/c14-3-1-7-6-17-12(20)8-5-10(18-11(7)8)9-2-4-16-13(15)19-9/h2,4-5,7,18H,1,3,6H2,(H,17,20)(H2,15,16,19)/t7-/m0/s1
comment: Compound 89S is a lead compound identified as a cell division cycle 7 (CDC7) inhibitor <Reference id=26881/>. The article reporting its discovery provides details of a large series of small molecules, several more of which potently inhibit CDC7 <Reference id=26881/>.
iupac name: (7S)-2-(2-aminopyrimidin-4-yl)-7-(2-fluoroethyl)-1,5,6,7-tetrahydropyrrolo[3,2-c]pyridin-4-one
xref: CHEMBL524266
approved: f
ligand name: compound 89S [PMID: 19115845]
type: SyntheticOrganicLigand

XL413
canonical SMILES: Clc1ccc2c(c1)c1[nH]c(nc(=O)c1o2)C1CCCN1
in ch i key: JJWLXRKVUJDJKG-VIFPVBQESA-N
in ch i: InChI=1S/C14H12ClN3O2/c15-7-3-4-10-8(6-7)11-12(20-10)14(19)18-13(17-11)9-2-1-5-16-9/h3-4,6,9,16H,1-2,5H2,(H,17,18,19)/t9-/m0/s1
comment: XL413 was developed as a selective inhibitor of cell division cycle 7 (CDC7) <Reference id=26879/> and was investigated for its antineoplastic effects.
iupac name: 8-chloro-2-[(2S)-pyrrolidin-2-yl]-1H-[1]benzofuro[3,2-d]pyrimidin-4-one
xref: CHEMBL2030402
synonym: BMS-863233
synonym: BMS863233
synonym: BMS 863233
synonym: XL-413
approved: f
ligand name: XL413
type: SyntheticOrganicLigand

GW5074
isomeric SMILES: Ic1ccc2c(c1)/C(=C/c1cc(Br)c(c(c1)Br)O)/C(=O)N2
in ch i key: LMXYVLFTZRPNRV-KMKOMSMNSA-N
in ch i: InChI=1S/C15H8Br2INO2/c16-11-4-7(5-12(17)14(11)20)3-10-9-6-8(18)1-2-13(9)19-15(10)21/h1-6,20H,(H,19,21)/b10-3-
comment: GW5074 is a potent and selective inhibitor of Raf-1 proto-oncogene, serine/threonine kinase RAF1 (aka c-Raf) in vitro <Reference id=26639/>. It was tested in preclinical studies.
iupac name: 3-[(3,5-dibromo-4-hydroxyphenyl)methylidene]-5-iodo-1H-indol-2-one
xref: CHEMBL72365
synonym: Raf1 kinase inhibitor I
synonym: GW 5074
synonym: GW-5074
approved: f
ligand name: GW5074
type: SyntheticOrganicLigand

compound 2-13-1 [PMID: 24900824]
in ch i key: FFVPQWXBEUUBMF-UHFFFAOYSA-N
in ch i: InChI=1S/C26H26FN7O4S/c1-39(36,37)12-11-38-22-14-30-26(32-25(22)31-20-9-10-29-13-18(20)24(28)35)23-17-6-4-8-21(17)34(33-23)15-16-5-2-3-7-19(16)27/h2-3,5,7,9-10,13-14H,4,6,8,11-12,15H2,1H3,(H2,28,35)(H,29,30,31,32)
comment: This BUB1 (BUB1 mitotic checkpoint serine/threonine kinase) inhibitor compound was developed as a potential antineoplastic and was granted patent protection in 2013 <Reference id=26877/>.
iupac name: 4-[(2-{1-[(2-fluorophenyl)methyl]-1H,4H,5H,6H-cyclopenta[c]pyrazol-3-yl}-5-(2-methanesulfonylethoxy)pyrimidin-4-yl)amino]pyridine-3-carboxamide
xref: CHEMBL3260329
approved: f
ligand name: compound 2-13-1 [PMID: 24900824]
type: SyntheticOrganicLigand

PF-06447475
canonical SMILES: N#Cc1cccc(c1)c1c[nH]c2c1c(ncn2)N1CCOCC1
isomeric SMILES: N#Cc1cccc(c1)c1c[nH]c2c1c(ncn2)N1CCOCC1
in ch i key: BHTWDJBVZQBRKP-UHFFFAOYSA-N
in ch i: InChI=1S/C17H15N5O/c18-9-12-2-1-3-13(8-12)14-10-19-16-15(14)17(21-11-20-16)22-4-6-23-7-5-22/h1-3,8,10-11H,4-7H2,(H,19,20,21)
comment: PF-06447475 has been identified as a potent, brain-pentrant inhibitor of the serine-threonine kinase, leucine-rich repeat kinase 2 (LRRK2) <Reference id=26622/> . The compound does not have favourable pharmacokinetic properties to progress clinical development, but it is a useful tool for the investigation of central and peripheral LRRK2 function.
iupac name: 3-[4-(morpholin-4-yl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl]benzonitrile
approved: f
ligand name: PF-06447475
type: SyntheticOrganicLigand

compound 2-3-1 [PMID: 24900824]
in ch i key: HDLPONLLJOSAIM-UHFFFAOYSA-N
in ch i: InChI=1S/C28H31F2N7O2/c1-4-38-19-14-22(29)21(23(30)15-19)17-37-24-7-5-6-20(24)26(35-37)28-32-16-25(39-13-12-36(2)3)27(34-28)33-18-8-10-31-11-9-18/h8-11,14-16H,4-7,12-13,17H2,1-3H3,(H,31,32,33,34)
comment: This BUB1 (BUB1 mitotic checkpoint serine/threonine kinase) inhibitor compound was developed as a potential antineoplastic and was granted patent protection in 2013 <Reference id=26877/>.
iupac name: 5-[2-(dimethylamino)ethoxy]-2-[1-[(4-ethoxy-2,6-difluorophenyl)methyl]-5,6-dihydro-4H-cyclopenta[c]pyrazol-3-yl]-N-pyridin-4-ylpyrimidin-4-amine
xref: CHEMBL3260325
approved: f
ligand name: compound 2-3-1 [PMID: 24900824]
type: SyntheticOrganicLigand

compound 2-3-2 [PMID: 24900824]
in ch i key: WIVMUEFNJYZIOY-UHFFFAOYSA-N
in ch i: InChI=1S/C29H30F2N6O4/c1-2-40-19-10-22(30)21(23(31)11-19)13-37-24-5-3-4-20(24)26(36-37)28-33-12-25(41-17-29(14-38)15-39-16-29)27(35-28)34-18-6-8-32-9-7-18/h6-12,38H,2-5,13-17H2,1H3,(H,32,33,34,35)
comment: This BUB1 (BUB1 mitotic checkpoint serine/threonine kinase) inhibitor compound was developed as a potential antineoplastic and was granted patent protection in 2013 <Reference id=26877/>.
iupac name: [3-[[2-[1-[(4-ethoxy-2,6-difluorophenyl)methyl]-5,6-dihydro-4H-cyclopenta[c]pyrazol-3-yl]-4-(pyridin-4-ylamino)pyrimidin-5-yl]oxymethyl]oxetan-3-yl]methanol
xref: CHEMBL3260326
approved: f
ligand name: compound 2-3-2 [PMID: 24900824]
type: SyntheticOrganicLigand

compound 2-1-1 [PMID: 24900824]
in ch i key: UJORPFQWUKFXIE-UHFFFAOYSA-N
in ch i: InChI=1S/C25H24F2N6O2/c1-3-35-16-11-19(26)18(20(27)12-16)14-33-21-6-4-5-17(21)23(32-33)25-29-13-22(34-2)24(31-25)30-15-7-9-28-10-8-15/h7-13H,3-6,14H2,1-2H3,(H,28,29,30,31)
comment: This BUB1 (BUB1 mitotic checkpoint serine/threonine kinase) inhibitor compound was developed as a potential antineoplastic and was granted patent protection in 2013 <Reference id=26877/>.
iupac name: 2-[1-[(4-ethoxy-2,6-difluorophenyl)methyl]-5,6-dihydro-4H-cyclopenta[c]pyrazol-3-yl]-5-methoxy-N-pyridin-4-ylpyrimidin-4-amine
xref: CHEMBL3260324
approved: f
ligand name: compound 2-1-1 [PMID: 24900824]
type: SyntheticOrganicLigand

denfivontinib
in ch i key: SXWMIXPJPNCXQQ-UHFFFAOYSA-N
in ch i: InChI=1S/C25H25BrN6O2/c1-32-13-11-17(12-14-32)29-25-30-22-20(26)15-27-24(33)21(22)23(31-25)28-16-7-9-19(10-8-16)34-18-5-3-2-4-6-18/h2-10,15,17H,11-14H2,1H3,(H,27,33)(H2,28,29,30,31)
comment: G-749 is a novel and potent inhibitor of wild type and mutant Fms-like tyrosine receptor kinase 3 (FLT3) <Reference id=26848/>. We matched its chemical structure to the INN 'denfivontinib' that was released in the WHO's proposed INN list 127 (21 July 2022).
iupac name: 8-bromo-2-[(1-methylpiperidin-4-yl)amino]-4-(4-phenoxyanilino)-6H-pyrido[4,3-d]pyrimidin-5-one
xref: CHEMBL4544478
synonym: G-749
synonym: G749
approved: f
ligand name: denfivontinib
type: SyntheticOrganicLigand

vactosertib
in ch i key: FJCDSQATIJKQKA-UHFFFAOYSA-N
in ch i: InChI=1S/C22H18FN7/c1-14-5-4-8-18(27-14)22-21(15-9-10-20-25-13-26-30(20)12-15)28-19(29-22)11-24-17-7-3-2-6-16(17)23/h2-10,12-13,24H,11H2,1H3,(H,28,29)
comment: The discovery of vactosertib (EW-7197) is reported in <Reference id=26847/> where it is compound 12b. EW-7197 acts as in inhibitor of transforming growth factor beta receptor 1B (TGFβR1; ALK5) and activin A receptor type IB (ACVR1B; ALK4). The compound is potent, selective, and orally bioavailable, and exhibits experimental anti-tumour activity.
iupac name: 2-fluoro-N-[[5-(6-methylpyridin-2-yl)-4-([1,2,4]triazolo[1,5-a]pyridin-6-yl)-1H-imidazol-2-yl]methyl]aniline
xref: CHEMBL3260567
synonym: TEW-7197
synonym: NOV-1301
synonym: EW-7197
synonym: EW7197
approved: f
ligand name: vactosertib
type: SyntheticOrganicLigand

URMC-099
in ch i key: QKKIWEILHCXECO-UHFFFAOYSA-N
in ch i: InChI=1S/C27H27N5/c1-31-10-12-32(13-11-31)18-19-2-4-20(5-3-19)23-15-24-25(17-30-27(24)29-16-23)21-6-7-26-22(14-21)8-9-28-26/h2-9,14-17,28H,10-13,18H2,1H3,(H,29,30)
comment: URMC-099 is an orally bioavailable, brain penetrant inhibitor of mixed lineage kinase 3 (MLK3) and leucine-rich repeat kinase 2 (LRRK2) <Reference id=26846/>. URMC-099 is being investigated as a lead compound with a novel mechanism of action for the treatment of Parkinson's disease and HIV-1 associated neurocognitive disorders (HAND).
iupac name: 3-(1H-indol-5-yl)-5-[4-[(4-methylpiperazin-1-yl)methyl]phenyl]-1H-pyrrolo[2,3-b]pyridine
xref: CHEMBL2436978
synonym: compound 1 [PMID 24044867]
approved: f
ligand name: URMC-099
type: SyntheticOrganicLigand

[3H]L-aspartic acid
canonical SMILES: OC(=O)CC(C(=O)O)N
isomeric SMILES: OC(=O)C[C@@H](C(=O)O)N
in ch i key: CKLJMWTZIZZHCS-REOHCLBHSA-N
in ch i: InChI=1S/C4H7NO4/c5-2(4(8)9)1-3(6)7/h2H,1,5H2,(H,6,7)(H,8,9)/t2-/m0/s1
iupac name: (2S)-2-aminobutanedioic acid
xref: CHEMBL274323
synonym: [3H]-L-aspartate
synonym: [3H]-L-aspartic acid
approved: f
ligand name: [3H]L-aspartic acid
type: SyntheticOrganicLigand

UMI-77
in ch i key: WUGANDSUVKXMEC-UHFFFAOYSA-N
comment: UMI-77 is a selective MCL1 (Q07820) inhibitor <Reference id=26845/>.
iupac name: 2-[4-[(4-bromophenyl)sulfonylamino]-1-hydroxynaphthalen-2-yl]sulfanylacetic acid
xref: CHEMBL1331211
approved: f
ligand name: UMI-77
type: SyntheticOrganicLigand

LY2874455
in ch i key: GKJCVYLDJWTWQU-CXLRFSCWSA-N
comment: LY2874455 is a potent ATP-competitive inhibitor of FGF receptors and VEGFR2 <Reference id=26844/>.
iupac name: 2-[4-[(E)-2-[5-[(1R)-1-(3,5-dichloropyridin-4-yl)ethoxy]-1H-indazol-3-yl]ethenyl]pyrazol-1-yl]ethanol
synonym: LY-2874455
approved: f
ligand name: LY2874455
type: SyntheticOrganicLigand

MI-3
in ch i key: FUGQNAUKABUDQI-UHFFFAOYSA-N
in ch i: InChI=1S/C18H25N5S2/c1-12(2)14-9-13-15(20-11-21-16(13)24-14)22-5-7-23(8-6-22)17-19-10-18(3,4)25-17/h9,11-12H,5-8,10H2,1-4H3
comment: MI-3 inhibits the interaction between MLL oncoproteins (re-arranged lysine (K)-specific methyltransferases) and the tumour suppressor protein menin (MEN1, O00255) <Reference id=26843/>. MI-3 represents a novel molecular mechanism with potential application in the treatment of aggressive leukemias with MLL rearrangements.
iupac name: 4-[4-(5,5-dimethyl-4H-1,3-thiazol-2-yl)piperazin-1-yl]-6-propan-2-ylthieno[2,3-d]pyrimidine
approved: f
ligand name: MI-3
type: SyntheticOrganicLigand

remodelin
canonical SMILES: N#Cc1ccc(cc1)c1csc(n1)NN=C1CCCC1
isomeric SMILES: N#Cc1ccc(cc1)c1csc(n1)NN=C1CCCC1
in ch i key: XAEJIFARBQJLML-UHFFFAOYSA-N
in ch i: InChI=1S/C15H14N4S/c16-9-11-5-7-12(8-6-11)14-10-20-15(17-14)19-18-13-3-1-2-4-13/h5-8,10H,1-4H2,(H,17,19)
comment: Remodelin is a reported to be an inhibitor of acetyl-transferase NAT10 (Q9H0A0) and gets its name from its ability to restore nuclear morphology in lamin A-depleted cells.
iupac name: 4-[2-(2-cyclopentylidenehydrazinyl)-1,3-thiazol-4-yl]benzonitrile
xref: CHEMBL399572
approved: f
ligand name: remodelin
type: SyntheticOrganicLigand

splitomicin
canonical SMILES: O=C1CCc2c(O1)ccc1c2cccc1
isomeric SMILES: O=C1CCc2c(O1)ccc1c2cccc1
in ch i key: ISFPDBUKMJDAJH-UHFFFAOYSA-N
in ch i: InChI=1S/C13H10O2/c14-13-8-6-11-10-4-2-1-3-9(10)5-7-12(11)15-13/h1-5,7H,6,8H2
comment: Splitomicin is a selective inhibitor of the yeast NAD+-dependent histone deacetylase Sir2 protein <Reference id=26838/>. Splitomicin has been used as a tool to elucidate the role of Sir2 in vivo <Reference id=26838/>. The human homologue of Sir2 is SIRT1. The SIRT histone deacetylases have been implicated in a wide range of cellular processes including stress resistance, metabolism, differentiation, and aging <Reference id=26837/>.
iupac name: 1,2-dihydrobenzo[f]chromen-3-one
xref: CHEMBL86537
approved: f
ligand name: splitomicin
type: SyntheticOrganicLigand

selisistat
canonical SMILES: NC(=O)C1CCCc2c1[nH]c1c2cc(cc1)Cl
isomeric SMILES: NC(=O)C1CCCc2c1[nH]c1c2cc(cc1)Cl
in ch i key: FUZYTVDVLBBXDL-UHFFFAOYSA-N
in ch i: InChI=1S/C13H13ClN2O/c14-7-4-5-11-10(6-7)8-2-1-3-9(13(15)17)12(8)16-11/h4-6,9,16H,1-3H2,(H2,15,17)
comment: Selisistat is a selective inhibitor of sirtuin 1 (SIRT1) catalytic activity <Reference id=26836/><Reference id=40183/>. SIRT1 is an enzyme which deacetylates the p53 tumor suppressor protein and may modulate p53-dependent functions such as DNA damage-induced cell death. The SIRT histone deacetylases have been implicated in a wide range of cellular processes including stress resistance, metabolism, differentiation, and aging <Reference id=26837/>.
iupac name: 6-chloro-2,3,4,9-tetrahydro-1H-carbazole-1-carboxamide
xref: CHEMBL420311
synonym: EX-527
synonym: EX 527
synonym: EX527
synonym: SEN0014196
approved: f
ligand name: selisistat
type: SyntheticOrganicLigand

AGK2
in ch i key: SVENPFFEMUOOGK-SDNWHVSQSA-N
comment: AGK2 is a selective sirtuin 2 (SIRT2) inhibitor <Reference id=26835/>. The sirtuins are members of the histone deacetylase family. The SIRT histone deacetylases have been implicated in a wide range of cellular processes including stress resistance, metabolism, differentiation, and aging <Reference id=26837/>.
iupac name: (E)-2-cyano-3-[5-(2,5-dichlorophenyl)furan-2-yl]-N-quinolin-5-ylprop-2-enamide
xref: CHEMBL224864
synonym: AGK-2
synonym: AGK 2
approved: f
ligand name: AGK2
type: SyntheticOrganicLigand

tasquinimod
in ch i key: ONDYALNGTUAJDX-UHFFFAOYSA-N
in ch i: InChI=1S/C20H17F3N2O4/c1-24(12-9-7-11(8-10-12)20(21,22)23)18(27)16-17(26)15-13(25(2)19(16)28)5-4-6-14(15)29-3/h4-10,26H,1-3H3
comment: Tasquinimod is an orally active allosteric inhibitor of HDAC4 <Reference id=26834/>. It has antiangiogenic effects.
iupac name: 4-hydroxy-5-methoxy-N,1-dimethyl-2-oxo-N-[4-(trifluoromethyl)phenyl]quinoline-3-carboxamide
xref: CHEMBL2107784
synonym: ABR-215050
approved: f
ligand name: tasquinimod
type: SyntheticOrganicLigand

brivanib alinate
in ch i key: LTEJRLHKIYCEOX-OCCSQVGLSA-N
in ch i: InChI=1S/C22H24FN5O4/c1-11-7-15-16(27-11)5-6-17(19(15)23)32-21-20-13(3)18(8-28(20)26-10-25-21)30-9-12(2)31-22(29)14(4)24/h5-8,10,12,14,27H,9,24H2,1-4H3/t12-,14+/m1/s1
iupac name: [(2R)-1-[4-[(4-fluoro-2-methyl-1H-indol-5-yl)oxy]-5-methylpyrrolo[5,1-f][1,2,4]triazin-6-yl]oxypropan-2-yl] (2S)-2-aminopropanoate
xref: CHEMBL270995
synonym: BMS-582664
synonym: BMS582664
synonym: BMS 582664
approved: f
ligand name: brivanib alinate
type: SyntheticOrganicLigand

BIBF-1202
isomeric SMILES: CN1CCN(CC1)CC(=O)N(c1ccc(cc1)N/C(=C/1/C(=O)Nc2c1ccc(c2)C(=O)O)/c1ccccc1)C
in ch i key: KEHNCEDHZGQSNP-DQSJHHFOSA-N
in ch i: InChI=1S/C30H31N5O4/c1-33-14-16-35(17-15-33)19-26(36)34(2)23-11-9-22(10-12-23)31-28(20-6-4-3-5-7-20)27-24-13-8-21(30(38)39)18-25(24)32-29(27)37/h3-13,18,31H,14-17,19H2,1-2H3,(H,32,37)(H,38,39)/b28-27-
comment: BIBF-1202 is the major metabolite of <Ligand id=5936/>, produced by methyl ester cleavage <Reference id=26829/>.
iupac name: (3Z)-3-[[[4-[methyl-[2-(4-methylpiperazin-1-yl)acetyl]amino]phenyl]amino]-phenylmethylidene]-2-oxo-1H-indole-6-carboxylic acid
synonym: BIBF 1202
approved: f
ligand name: BIBF-1202
type: SyntheticOrganicLigand

AC710
in ch i key: JVCWPUFNLFSKFS-UHFFFAOYSA-N
in ch i: InChI=1S/C31H42N6O4/c1-9-37-30(5,6)17-23(18-31(37,7)8)40-22-14-15-24(32-19-22)27(38)33-20-10-12-21(13-11-20)34-28(39)35-26-16-25(41-36-26)29(2,3)4/h10-16,19,23H,9,17-18H2,1-8H3,(H,33,38)(H2,34,35,36,39)
comment: The design and synthesis of AC710 is described in <Reference id=26787/>, where it is compound 22b. AC710 is reported as an inhibitor of platelet-derived growth factor receptor (PDGFR) family receptor tyrosine kinases (RTKs). The compound has favourable pharmacodynamics and pharmacokinetics, and is active against mouse xenograft tumours and in a collagen-induced arthritis (CIA) model <Reference id=26787/>.
iupac name: N-(4-{[(5-tert-butyl-1,2-oxazol-3-yl)carbamoyl]amino}phenyl)-5-[(1-ethyl-2,2,6,6-tetramethylpiperidin-4-yl)oxy]pyridine-2-carboxamide
xref: CHEMBL2206278
synonym: AC-710
synonym: AC 710
approved: f
ligand name: AC710
type: SyntheticOrganicLigand

AG14361
canonical SMILES: CN(Cc1ccc(cc1)c1nc2c3n1CCNC(=O)c3ccc2)C
isomeric SMILES: CN(Cc1ccc(cc1)c1nc2c3n1CCNC(=O)c3ccc2)C
in ch i key: SEKJSSBJKFLZIT-UHFFFAOYSA-N
in ch i: InChI=1S/C19H20N4O/c1-22(2)12-13-6-8-14(9-7-13)18-21-16-5-3-4-15-17(16)23(18)11-10-20-19(15)24/h3-9H,10-12H2,1-2H3,(H,20,24)
comment: AG14361 is a potent experimental inhibitor of poly (ADP-ribose) polymerase 1 (PARP1) <Reference id=26416/>. Its discovery is described in <Reference id=26784/>, where it is compound 22.
xref: CHEMBL65892
synonym: AG-14361
synonym: AG 14361
approved: f
ligand name: AG14361
type: SyntheticOrganicLigand

compound 7 [WO2012007375]
in ch i key: BUJSZRICYLPWCM-UHFFFAOYSA-N
in ch i: InChI=1S/C20H20N6O2S/c1-26(7-5-21)20-23-10-17-18(25-20)13(11-29-17)19(27)24-15-8-12-4-3-6-22-14(12)9-16(15)28-2/h3-4,6,8-11H,5,7,21H2,1-2H3,(H,24,27)
comment: This compound is a potent and somewhat selective inhibitor of IRAK4, described in patent WO2012007375 <Reference id=26661/>.
iupac name: 2-[(2-aminoethyl)(methyl)amino]-N-(7-methoxyquinolin-6-yl)thieno[3,2-d]pyrimidine-7-carboxamide
approved: f
ligand name: compound 7 [WO2012007375]
type: SyntheticOrganicLigand

compound 1 [WO2012007375]
in ch i key: BNVZRFQNZWYPQH-UHFFFAOYSA-N
in ch i: InChI=1S/C19H21ClN6O2/c20-13-1-2-17(25-5-3-12(8-21)4-6-25)16(7-13)24-19(28)15-10-23-26-11-14(27)9-22-18(15)26/h1-2,7,9-12,27H,3-6,8,21H2,(H,24,28)
comment: Development of this compound is covered in patent WO2012007375 <Reference id=26661/>. It is a potent IRAK4 inhibitor.
iupac name: N-{2-[4-(aminomethyl)piperidin-1-yl]-5-chlorophenyl}-6-hydroxypyrazolo[1,5-a]pyrimidine-3-carboxamide
approved: f
ligand name: compound 1 [WO2012007375]
type: SyntheticOrganicLigand

ND-2158
in ch i key: ZSMULWAVKYFPSS-FPCVCCKLSA-N
in ch i: InChI=1S/C22H30N4O4S/c23-20(28)16(27)11-13-1-6-17-18(13)19-21(24-12-25-22(19)31-17)30-15-4-2-14(3-5-15)26-7-9-29-10-8-26/h12-16,27H,1-11H2,(H2,23,28)/t13-,14-,15-,16+/m1/s1
comment: ND-2158 is a potent and selective experimental inhibitor of IRAK4 described in patent WO2013106535 <Reference id=26659/> and in a poster presented at the American College of Rheumatology meeting in 2012 (Abstract #1062 in Supplement: Abstracts of the American College of Rheumatology & Association of Rheumatology Health Professionals, Annual Scientific Meeting, November 9-4, 2012 Washington DC, Volume 64, Issue S10, Page S1-S1216). PubChem CID 86343751 represents this molecule with alternative stereochemisrty.
iupac name: (2S)-2-hydroxy-3-[(3R)-12-{[(1r,4r)-4-(morpholin-4-yl)cyclohexyl]oxy}-7-thia-9,11-diazatricyclo[6.4.0.0²,⁶]dodeca-1(12),2(6),8,10-tetraen-3-yl]propanamide
approved: f
ligand name: ND-2158
type: SyntheticOrganicLigand

ND-2110
in ch i key: VZOLINZYKOLXAC-RBSFLKMASA-N
in ch i: InChI=1S/C21H28N4O3S/c22-17(26)11-13-1-6-16-18(13)19-20(23-12-24-21(19)29-16)28-15-4-2-14(3-5-15)25-7-9-27-10-8-25/h12-15H,1-11H2,(H2,22,26)/t13-,14-,15-/m1/s1
comment: ND-2110 is a potent and selective experimental inhibitor of IRAK4 described in patent WO2013106535 <Reference id=26659/> and in a poster presented at the American College of Rheumatology meeting in 2012 (Abstract #1062 in Supplement: Abstracts of the American College of Rheumatology & Association of Rheumatology Health Professionals, Annual Scientific Meeting, November 9-4, 2012 Washington DC, Volume 64, Issue S10, Page S1-S1216). PubChem CID 68115559 represents this molecule with specified stereochemisrty at only one of the chiral centers.
iupac name: 2-[(3R)-12-{[(1r,4r)-4-(morpholin-4-yl)cyclohexyl]oxy}-7-thia-9,11-diazatricyclo[6.4.0.0²,⁶]dodeca-1(12),2(6),8,10-tetraen-3-yl]acetamide
approved: f
ligand name: ND-2110
type: SyntheticOrganicLigand

IRAK4 inhibitor rac-45 [PMID: 18501603]
canonical SMILES: Clc1ccc2n(c1)c(cn2)c1cccc(n1)NC1CNCC1
isomeric SMILES: Clc1ccc2n(c1)c(cn2)c1cccc(n1)NC1CNCC1
in ch i key: NAMQQRIYZTTYCJ-UHFFFAOYSA-N
in ch i: InChI=1S/C16H16ClN5/c17-11-4-5-16-19-9-14(22(16)10-11)13-2-1-3-15(21-13)20-12-6-7-18-8-12/h1-5,9-10,12,18H,6-8H2,(H,20,21)
comment: This is an experimental inhibitor of IRAK4 discovered by high throughput screening <Reference id=26658/>.
iupac name: 6-{6-chloroimidazo[1,2-a]pyridin-3-yl}-N-(pyrrolidin-3-yl)pyridin-2-amine
xref: CHEMBL401633
approved: f
ligand name: IRAK4 inhibitor rac-45 [PMID: 18501603]
type: SyntheticOrganicLigand

IRAK4 inhibitor 4b [PMID: 18474425]
in ch i key: RAFFLDOJXQAJPF-UHFFFAOYSA-N
in ch i: InChI=1S/C20H21N5O3/c1-27-19-13-14(25-9-11-28-12-10-25)5-6-17(19)23-20(26)18-4-2-3-15(22-18)16-7-8-21-24-16/h2-8,13H,9-12H2,1H3,(H,21,24)(H,23,26)
comment: This is an experimental inhibitor of IRAK4 discovered by high throughput screening <Reference id=26657/>.
iupac name: N-[2-methoxy-4-(morpholin-4-yl)phenyl]-6-(1H-pyrazol-5-yl)pyridine-2-carboxamide
xref: CHEMBL256713
approved: f
ligand name: IRAK4 inhibitor 4b [PMID: 18474425]
type: SyntheticOrganicLigand

HX 531
in ch i key: SXKPGYKPQPYJER-UHFFFAOYSA-N
in ch i: InChI=1S/C29H29N3O4/c1-28(2)12-13-29(3,4)22-16-25-20(15-21(22)28)26(17-6-8-18(9-7-17)27(33)34)30-23-14-19(32(35)36)10-11-24(23)31(25)5/h6-11,14-16H,12-13H2,1-5H3,(H,33,34)
comment: HX 531 is an antagonist of retinoid X receptors <Reference id=30133/><Reference id=22804/>. Antagonism is generally assessed as the ability of HX 531 to inhibit agonist-induced transactivation of the retinoid X receptors.
iupac name: 4-(5,7,7,10,10-pentamethyl-2-nitro-8,9-dihydronaphtho[2,3-b][1,5]benzodiazepin-12-yl)benzoic acid
xref: CHEMBL326525
synonym: HX-531
synonym: HX531
approved: f
ligand name: HX 531
type: SyntheticOrganicLigand

5Z-7-oxozeaenol
isomeric SMILES: COc1cc2/C=C/C[C@H](O)[C@H](O)C(=O)/C=C/C[C@@H](OC(=O)c2c(c1)O)C
in ch i key: NEQZWEXWOFPKOT-BYRRXHGESA-N
in ch i: InChI=1S/C19H22O7/c1-11-5-3-7-14(20)18(23)15(21)8-4-6-12-9-13(25-2)10-16(22)17(12)19(24)26-11/h3-4,6-7,9-11,15,18,21-23H,5,8H2,1-2H3/b6-4+,7-3-/t11-,15-,18+/m0/s1
comment: 5Z-7-oxozeaenol is a cell-permeable fungal resorcylic lactone. 5Z-7-oxozeaenol acts as a selective and potent inhibitor of mitogen-activated protein kinase kinase kinase 7 (TAK1). This compound binds covalently/irreversibly and inhibits both the ATPase and kinase activity of TAK1 <Reference id=19741/>.
iupac name: (2E,5S,6S,8Z,11S)-5,6,15-trihydroxy-17-methoxy-11-methyl-12-oxabicyclo[12.4.0]octadeca-1(14),2,8,15,17-pentaene-7,13-dione
xref: CHEMBL1077979
synonym: (5Z)-7-oxozeaenol
synonym: LL-Z1640-2
synonym: FR-148083
synonym: (5Z)-7-Oxozeaenol
approved: f
ligand name: 5Z-7-oxozeaenol
type: SyntheticOrganicLigand

MSC2032964A
in ch i key: XUKGFHHTSUKORV-UHFFFAOYSA-N
in ch i: InChI=1S/C16H13F3N6O/c17-16(18,19)10-6-12(21-11-3-4-11)25-13(7-10)22-15(24-25)23-14(26)9-2-1-5-20-8-9/h1-2,5-8,11,21H,3-4H2,(H,23,24,26)
comment: MSC2032964A is a hit compound identified in <Reference id=26645/>. MSC2032964A is an inhibitor of mitogen-activated protein kinase kinase kinase 5 (MAP3K5, aka ASK1). It was tested in preclinical studies.
iupac name: N-[5-(cyclopropylamino)-7-(trifluoromethyl)[1,2,4]triazolo[1,5-a]pyridin-2-yl]-3-pyridinecarboxamide
approved: f
ligand name: MSC2032964A
type: SyntheticOrganicLigand

LY2109761
in ch i key: IHLVSLOZUHKNMQ-UHFFFAOYSA-N
in ch i: InChI=1S/C26H27N5O2/c1-2-9-27-22(4-1)26-25(24-5-3-11-31(24)29-26)21-8-10-28-23-18-19(6-7-20(21)23)33-17-14-30-12-15-32-16-13-30/h1-2,4,6-10,18H,3,5,11-17H2
comment: LY2109761 is an investigational, selective inhibitor of TGFβ receptors type 1 and 2 (TGFBR1 and TGFBR2) <Reference id=26643/>.
iupac name: 7-(2-morpholin-4-ylethoxy)-4-(2-pyridin-2-yl-5,6-dihydro-4H-pyrrolo[2,1-e]pyrazol-3-yl)quinoline
xref: CHEMBL260015
synonym: LY-2109761
synonym: LY 2109761
approved: f
ligand name: LY2109761
type: SyntheticOrganicLigand

NG-25
in ch i key: SMPGEBOIKULBCT-UHFFFAOYSA-N
in ch i: InChI=1S/C29H30F3N5O2/c1-3-36-12-14-37(15-13-36)18-21-6-7-22(17-24(21)29(30,31)32)35-28(38)20-5-4-19(2)26(16-20)39-25-9-11-34-27-23(25)8-10-33-27/h4-11,16-17H,3,12-15,18H2,1-2H3,(H,33,34)(H,35,38)
comment: NG-25 is an experimental inhibitor of several protein kinease, including mitogen-activated protein kinase kinase kinase 7 (TAK1, aka TGF-β-activated kinase 1), but it is not selective. Results from a screening set are provided by Tan et al (2015) <Reference id=26642/>.
iupac name: N-[4-[(4-ethylpiperazin-1-yl)methyl]-3-(trifluoromethyl)phenyl]-4-methyl-3-(1H-pyrrolo[2,3-b]pyridin-4-yloxy)benzamide
synonym: NG25
approved: f
ligand name: NG-25
type: SyntheticOrganicLigand

GNE-7915
in ch i key: XCFLWTZSJYBCPF-UHFFFAOYSA-N
in ch i: InChI=1S/C19H21F4N5O3/c1-3-24-16-12(19(21,22)23)10-25-18(27-16)26-14-9-13(20)11(8-15(14)30-2)17(29)28-4-6-31-7-5-28/h8-10H,3-7H2,1-2H3,(H2,24,25,26,27)
comment: GNE-7915 is a highly potent, selective, and brain-penetrating inhibitor of leucine-rich repeat kinase 2 (LRRK2) <Reference id=26640/>. It was tested in preclinical studies.
iupac name: [4-[[4-(ethylamino)-5-(trifluoromethyl)pyrimidin-2-yl]amino]-2-fluoro-5-methoxyphenyl]-morpholin-4-ylmethanone
xref: CHEMBL2178134
synonym: GNE7915
synonym: GNE 7915
approved: f
ligand name: GNE-7915
type: SyntheticOrganicLigand

GNF-5837
in ch i key: YYDUWLSETXNJJT-MTJSOVHGSA-N
in ch i: InChI=1S/C28H21F4N5O2/c1-15-4-6-19(35-27(39)37-25-11-16(28(30,31)32)5-9-22(25)29)13-23(15)34-18-7-8-20-21(12-17-3-2-10-33-17)26(38)36-24(20)14-18/h2-14,33-34H,1H3,(H,36,38)(H2,35,37,39)/b21-12-
comment: GNF-5837 is an investigational, selective, and orally bioavailable inhibitor of the neurotrophic receptor tyrosine kinases TrkA, TrkB and TrkC <Reference id=24932/>. This compound is a useful tool for the investigation of TRK biology in human diseases.
iupac name: 1-[2-fluoro-5-(trifluoromethyl)phenyl]-3-[4-methyl-3-[[(3Z)-2-oxo-3-(1H-pyrrol-2-ylmethylidene)-1H-indol-6-yl]amino]phenyl]urea
xref: CHEMBL2037226
synonym: GNF 5837
synonym: GNF5837
approved: f
ligand name: GNF-5837
type: SyntheticOrganicLigand

6-aminocaproic acid
canonical SMILES: NCCCCCC(=O)O
isomeric SMILES: NCCCCCC(=O)O
in ch i key: SLXKOJJOQWFEFD-UHFFFAOYSA-N
in ch i: InChI=1S/C6H13NO2/c7-5-3-1-2-4-6(8)9/h1-5,7H2,(H,8,9)
comment: Aminocaproic acid is a derivative of lysine.
iupac name: 6-aminohexanoic acid
xref: CHEMBL1046
synonym: ε-aminocaproic acid
synonym: Acepramin
synonym: Acepramine
synonym: Afibrin
synonym: Amikar
synonym: Aminokapron
synonym: Amicar®
synonym: Atsemin
synonym: Caplamin
synonym: Capracid
synonym: Capramol
synonym: Capranol
synonym: Caprocid
synonym: Caprolisin
synonym: EACS
synonym: Epsamon
synonym: Epsicapron
synonym: Epsikapron
synonym: Epsilcapramin
synonym: Epsilcapramine
synonym: Hemocaprol
synonym: Hemopar
synonym: Hepin
synonym: Ipsilon
synonym: Respramin
synonym: EACA
approved: t
ligand name: 6-aminocaproic acid
type: SyntheticOrganicLigand

P505-15
in ch i key: TXGKRVFSSHPBAJ-JKSUJKDBSA-N
in ch i: InChI=1S/C19H23N9O/c20-15-6-1-2-7-16(15)26-19-22-11-14(17(21)29)18(27-19)25-12-4-3-5-13(10-12)28-23-8-9-24-28/h3-5,8-11,15-16H,1-2,6-7,20H2,(H2,21,29)(H2,22,25,26,27)/t15-,16+/m0/s1
comment: P505-15 is an investigational, potent and selective inhibitor of spleen tyrosine kinase (Syk) <Reference id=26638/>. This is a tool compound suitable for analysis of the role played by Syk in modulating immune function in human diseases. The compound may be used as the hydrochloride salt.
iupac name: 2-[[(1R,2S)-2-aminocyclohexyl]amino]-4-[3-(triazol-2-yl)anilino]pyrimidine-5-carboxamide
xref: CHEMBL2177736
synonym: BIIB057
synonym: PRT062607
synonym: PRT-062607
approved: f
ligand name: P505-15
type: SyntheticOrganicLigand

CP-673451
in ch i key: DEEOXSOLTLIWMG-UHFFFAOYSA-N
in ch i: InChI=1S/C24H27N5O2/c1-30-13-14-31-19-6-7-21-20(15-19)26-16-29(21)23-8-5-17-3-2-4-22(24(17)27-23)28-11-9-18(25)10-12-28/h2-8,15-16,18H,9-14,25H2,1H3
comment: CP-673451 is an investigational, selective inhibitor of PDGFRα and PDGFRβ <Reference id=26637/>.
iupac name: 1-[2-[5-(2-methoxyethoxy)benzimidazol-1-yl]quinolin-8-yl]piperidin-4-amine
synonym: CP-673,451
approved: f
ligand name: CP-673451
type: SyntheticOrganicLigand

WH-4-023
in ch i key: NBTNHSGBRGTFJS-UHFFFAOYSA-N
in ch i: InChI=1S/C32H36N6O4/c1-22-7-6-8-23(2)30(22)42-32(39)38(27-14-13-26(40-4)21-28(27)41-5)29-15-16-33-31(35-29)34-24-9-11-25(12-10-24)37-19-17-36(3)18-20-37/h6-16,21H,17-20H2,1-5H3,(H,33,34,35)
comment: WH-4-023 is an investigational inhibitor of the kinases LCK proto-oncogene, Src family tyrosine kinase (Lck) and SRC proto-oncogene, non-receptor tyrosine kinase (Src) <Reference id=26636/>. It is compound 28 in <Reference id=26636/>, where it is reported to be potent and orally active in preclinical models.
iupac name: (2,6-dimethylphenyl) N-(2,4-dimethoxyphenyl)-N-[2-[[4-(4-methylpiperazin-1-yl)phenyl]amino]pyrimidin-4-yl]carbamate
xref: CHEMBL213100
approved: f
ligand name: WH-4-023
type: SyntheticOrganicLigand

NVP-AEW541
in ch i key: AECDBHGVIIRMOI-UHFFFAOYSA-N
in ch i: InChI=1S/C27H29N5O/c28-26-25-24(21-8-4-9-23(14-21)33-17-19-6-2-1-3-7-19)16-32(27(25)30-18-29-26)22-12-20(13-22)15-31-10-5-11-31/h1-4,6-9,14,16,18,20,22H,5,10-13,15,17H2,(H2,28,29,30)
comment: NVP-AEW541 is a potent and selective inhibitor of the receptor tyrosine kinase, insulin-like growth factor I receptor (IGF1R) <Reference id=26635/>. It was tested in preclinical studies.
iupac name: 7-[3-(azetidin-1-ylmethyl)cyclobutyl]-5-[3-(phenylmethoxy)phenyl]pyrrolo[3,2-e]pyrimidin-4-amine
xref: CHEMBL3188172
synonym: AEW541
synonym: NVP AEW541
synonym: NVP-AEW 541
synonym: AEW-541
synonym: AEW 541
synonym: NVP-AEW541-A
approved: f
ligand name: NVP-AEW541
type: SyntheticOrganicLigand

CGI1746
in ch i key: JIFCFQDXHMUPGP-UHFFFAOYSA-N
in ch i: InChI=1S/C34H37N5O4/c1-22-27(7-6-8-28(22)37-31(40)23-9-13-25(14-10-23)34(2,3)4)29-21-38(5)33(42)30(36-29)35-26-15-11-24(12-16-26)32(41)39-17-19-43-20-18-39/h6-16,21H,17-20H2,1-5H3,(H,35,36)(H,37,40)
comment: CGI1746 is a potent and highly selective small-molecule inhibitor of the Tec family kinase, Bruton agammaglobulinemia tyrosine kinase (BTK) <Reference id=26634/>. It was a preclinical lead compound.
iupac name: 4-tert-butyl-N-[2-methyl-3-[4-methyl-6-[4-(morpholine-4-carbonyl)anilino]-5-oxopyrazin-2-yl]phenyl]benzamide
xref: CHEMBL1230541
synonym: CGI-1746
synonym: CGI 1746
approved: f
ligand name: CGI1746
type: SyntheticOrganicLigand

GNF-5
in ch i key: IIQUYGWWHIHOCF-UHFFFAOYSA-N
in ch i: InChI=1S/C20H17F3N4O3/c21-20(22,23)30-16-6-4-15(5-7-16)27-18-11-17(25-12-26-18)13-2-1-3-14(10-13)19(29)24-8-9-28/h1-7,10-12,28H,8-9H2,(H,24,29)(H,25,26,27)
comment: GNF-5 is an investigational selective and allosteric BCR-ABL inhibitor <Reference id=23009/>. GNF-5 is a pharmacokinetically optimised analogue of GNF-2 (PubChem CID 5311510) <Reference id=22997/>.
iupac name: N-(2-hydroxyethyl)-3-[6-[4-(trifluoromethoxy)anilino]pyrimidin-4-yl]benzamide
xref: CHEMBL1257423
synonym: GNF5
synonym: GNF 5
approved: f
ligand name: GNF-5
type: SyntheticOrganicLigand

BIX02188
isomeric SMILES: CN(Cc1cccc(c1)N/C(=C/1/C(=O)Nc2c1ccc(c2)C(=O)N)/c1ccccc1)C
in ch i key: FSZPIAXLCCQFCM-FCQUAONHSA-N
in ch i: InChI=1S/C25H24N4O2/c1-29(2)15-16-7-6-10-19(13-16)27-23(17-8-4-3-5-9-17)22-20-12-11-18(24(26)30)14-21(20)28-25(22)31/h3-14,27H,15H2,1-2H3,(H2,26,30)(H,28,31)/b23-22-
comment: BIX02188 is an investigational inhibitor of the STE7 family kinase, mitogen-activated protein kinase kinase 5 (MAP2K5) <Reference id=26633/>. This compound can be used as a pharmacological tool to help elucidate the role of the MEK5/ERK5 pathway in biological systems. BIX02188 is a closely related, marginally less potent, analogue of <Ligand id=9380/>. Both compounds have a similar selectivity profile. BIX02188 was tested in preclinical studies.
iupac name: (3Z)-3-[[3-[(dimethylamino)methyl]anilino]-phenylmethylidene]-2-oxo-1H-indole-6-carboxamide
synonym: BIX-02188
synonym: BIX 02188
approved: f
ligand name: BIX02188
type: SyntheticOrganicLigand

MRT67307
in ch i key: UKBGBACORPRCGG-UHFFFAOYSA-N
in ch i: InChI=1S/C26H36N6O2/c33-25(21-5-2-6-21)28-11-3-10-27-24-23(20-8-9-20)17-29-26(31-24)30-22-7-1-4-19(16-22)18-32-12-14-34-15-13-32/h1,4,7,16-17,20-21H,2-3,5-6,8-15,18H2,(H,28,33)(H2,27,29,30,31)
comment: MRT67307 is a non-selective inhibitor of TANK-binding kinase 1 (TBK1) <Reference id=26630/> with utility for the study of the roles played by IKKs and IKK-related kinases in the regulation of the type I interferon response in innate immunity.
iupac name: N-[3-[[5-cyclopropyl-2-[3-(morpholin-4-ylmethyl)anilino]pyrimidin-4-yl]amino]propyl]cyclobutanecarboxamide
synonym: MRT-67307
approved: f
ligand name: MRT67307
type: SyntheticOrganicLigand

MK-5108
in ch i key: LCVIRAZGMYMNNT-UHFFFAOYSA-N
comment: MK-5108 is a potent and selective inhibitor of Aurora kinase A (AURKA) <Reference id=26628/>.
iupac name: 4-(3-chloro-2-fluorophenoxy)-1-[[6-(1,3-thiazol-2-ylamino)pyridin-2-yl]methyl]cyclohexane-1-carboxylic acid
xref: CHEMBL3182444
synonym: MK5108
synonym: VX-689
synonym: VX 689
synonym: VX689
approved: f
ligand name: MK-5108
type: SyntheticOrganicLigand

AMG-900
in ch i key: IVUGFMLRJOCGAS-UHFFFAOYSA-N
in ch i: InChI=1S/C28H21N7OS/c1-17-15-24(37-16-17)25-20-5-2-3-6-21(20)26(35-34-25)32-18-8-10-19(11-9-18)36-27-22(7-4-13-30-27)23-12-14-31-28(29)33-23/h2-16H,1H3,(H,32,35)(H2,29,31,33)
comment: AMG-900 is a potent and selective pan-aurora kinase inhibitor <Reference id=26627/>.
iupac name: N-[4-[3-(2-aminopyrimidin-4-yl)pyridin-2-yl]oxyphenyl]-4-(4-methylthiophen-2-yl)phthalazin-1-amine
xref: CHEMBL2140408
synonym: AMG900
synonym: AMG 900
approved: f
ligand name: AMG-900
type: SyntheticOrganicLigand

AZD6482
in ch i key: IRTDIKMSKMREGO-OAHLLOKOSA-N
in ch i: InChI=1S/C22H24N4O4/c1-14-11-17(15(2)23-18-6-4-3-5-16(18)22(28)29)21-24-19(12-20(27)26(21)13-14)25-7-9-30-10-8-25/h3-6,11-13,15,23H,7-10H2,1-2H3,(H,28,29)/t15-/m1/s1
comment: AZD6482 is an inhibitor of phosphatidylinositol-3 kinase activity with selectivity for the β isozyme <Reference id=26626/>.
iupac name: 2-[[(1R)-1-(7-methyl-2-morpholin-4-yl-4-oxopyrido[1,2-a]pyrimidin-9-yl)ethyl]amino]benzoic acid
xref: CHEMBL2165191
synonym: AZD-6482
synonym: AZD 6482
approved: f
ligand name: AZD6482
type: SyntheticOrganicLigand

JNK-IN-8
in ch i key: GJFCSAPFHAXMSF-UXBLZVDNSA-N
in ch i: InChI=1S/C29H29N7O2/c1-20-17-24(11-12-25(20)34-29-31-15-13-26(35-29)22-8-5-14-30-19-22)33-28(38)21-7-4-9-23(18-21)32-27(37)10-6-16-36(2)3/h4-15,17-19H,16H2,1-3H3,(H,32,37)(H,33,38)(H,31,34,35)/b10-6+
comment: JNK-IN-8 is an inhibitor of the mitogen-activated protein kinases, JNK1, 2 and 3 <Reference id=26625/>. It was tested in preclinical studies.
iupac name: 3-[[(E)-4-(dimethylamino)but-2-enoyl]amino]-N-[3-methyl-4-[(4-pyridin-3-ylpyrimidin-2-yl)amino]phenyl]benzamide
xref: CHEMBL2216824
approved: f
ligand name: JNK-IN-8
type: SyntheticOrganicLigand

XMD8-92
in ch i key: QAPAJIZPZGWAND-UHFFFAOYSA-N
in ch i: InChI=1S/C26H30N6O3/c1-4-35-23-15-17(32-13-11-18(33)12-14-32)9-10-20(23)28-26-27-16-22-24(29-26)30(2)21-8-6-5-7-19(21)25(34)31(22)3/h5-10,15-16,18,33H,4,11-14H2,1-3H3,(H,27,28,29)
comment: XMD8-92 is an investigational inhibitor of the mitogen-activated protein kinase, ERK5 (mitogen-activated protein kinase 7, aka BMK1) <Reference id=26624/>. It was tested in preclinical studies.
iupac name: 2-[2-ethoxy-4-(4-hydroxypiperidin-1-yl)anilino]-5,11-dimethylpyrimido[4,5-b][1,4]benzodiazepin-6-one
xref: CHEMBL1673046
synonym: XMD 8-92
approved: f
ligand name: XMD8-92
type: SyntheticOrganicLigand

SCH772984
in ch i key: HDAJDNHIBCDLQF-RUZDIDTESA-N
in ch i: InChI=1S/C33H33N9O2/c43-30(42-18-16-41(17-19-42)27-5-2-24(3-6-27)32-35-11-1-12-36-32)22-40-15-10-25(21-40)33(44)37-26-4-7-29-28(20-26)31(39-38-29)23-8-13-34-14-9-23/h1-9,11-14,20,25H,10,15-19,21-22H2,(H,37,44)(H,38,39)/t25-/m1/s1
comment: SCH772984 is an experimental inhibitor of the mitogen-activated protein kinases ERK1 and ERK2 <Reference id=26623/>. The in vitro mechanism of action of SCH772984 is notable, in that it inhibits both the catalytic activity of ERK1/2 and also inhibits phosphorylation of ERK1/2. This is in contrast to other ERK inhibitors that target the ATP-binding site and thus inhibit only the catalytic activity of the kinases. The dual action of compounds like SCH772984 is predicted to block the nuclear localization of pERK and more completely suppress MAPK pathway signaling <Reference id=26623/>. This type of inhibitor may provide improved clinical efficacy, particularly in relation to the emergence of acquired resistance that occurs in BRAF and MEK inhibitor-treated cancers. Unfortunately, SCH772984 is not active in vivo (oral or intraperitoneal administration results in poor exposure levels) <Reference id=35141/>.
iupac name: (3R)-1-[2-oxo-2-[4-(4-pyrimidin-2-ylphenyl)piperazin-1-yl]ethyl]-N-(3-pyridin-4-yl-1H-indazol-5-yl)pyrrolidine-3-carboxamide
synonym: SCH-772984
approved: f
ligand name: SCH772984
type: SyntheticOrganicLigand

NVP-2
in ch i key: XWQVQSXLXAXOPJ-NJDAHSKKSA-N
in ch i: InChI=1S/C27H37ClN6O2/c1-19(16-35-2)32-20-6-8-21(9-7-20)33-26-14-22(23(28)15-30-26)24-4-3-5-25(34-24)31-18-27(17-29)10-12-36-13-11-27/h3-5,14-15,19-21,32H,6-13,16,18H2,1-2H3,(H,30,33)(H,31,34)/t19-,20-,21-/m1/s1
comment: NVP-2 is one of the compounds claimed in patent WO2011012661 <Reference id=26621/>. NVP-2 is an inhibitor of the cyclin-dependent kinase CDK9. It was a preclinical lead compound. PubChem CID 77201406 represents the compound without stereochemistry, and PubChem CID 66937006 has stereochemistry specified at only one of the chiral centers.
iupac name: 4-({[6-(5-chloro-2-{[(1r,4r)-4-{[(2R)-1-methoxypropan-2-yl]amino}cyclohexyl]amino}pyridin-4-yl)pyridin-2-yl]amino}methyl)oxane-4-carbonitrile
synonym: Example 93 [US8778951]
synonym: Compound 310 [US8778951]
approved: f
ligand name: NVP-2
type: SyntheticOrganicLigand

THZ1
in ch i key: OBJNFLYHUXWUPF-IZZDOVSWSA-N
in ch i: InChI=1S/C31H28ClN7O2/c1-39(2)16-6-11-28(40)35-21-14-12-20(13-15-21)30(41)36-22-7-5-8-23(17-22)37-31-34-19-26(32)29(38-31)25-18-33-27-10-4-3-9-24(25)27/h3-15,17-19,33H,16H2,1-2H3,(H,35,40)(H,36,41)(H,34,37,38)/b11-6+
comment: THZ1 is a covalent inhibitor of the cyclin-dependent kinase, CDK7 <Reference id=26620/>. The compound achieves CDK7 specificity by targeting a remote cysteine residue located outside of the canonical kinase domain. It was a preclinical lead compound. CDK7 inhibition by THZ1 has been demonstrated to overcome tumour resistance (primary or acquired) to smoothened inhibitor drugs (such as <Ligand id=8199/>, <Ligand id=6975/> and <Ligand id=8201/>), principally via suppressed synthesis of two core transcription factors belonging to the hedgehog pathway (the glioma-associated oncogenes GLI1 and GLI2) <Reference id=37839/>. This effect was detected in vitro and in vivo. CDK7 inhibition has been shown to overcome resistance to HER2-targeted inhibitors in HER2 +ve breast cancer cells and in xenograft models <Reference id=38210/>.
iupac name: N-[3-[[5-chloro-4-(1H-indol-3-yl)pyrimidin-2-yl]amino]phenyl]-4-[[(E)-4-(dimethylamino)but-2-enoyl]amino]benzamide
synonym: HY-80013
approved: f
ligand name: THZ1
type: SyntheticOrganicLigand

BMS-265246
in ch i key: SCFMWQIQBVZOQR-UHFFFAOYSA-N
in ch i: InChI=1S/C18H17F2N3O2/c1-3-4-5-25-17-11(8-21-18-12(17)9-22-23-18)16(24)15-13(19)6-10(2)7-14(15)20/h6-9H,3-5H2,1-2H3,(H,21,22,23)
comment: BMS-265246 is a potent and selective inhibitor of the cyclin-dependent kinases, CDK1 and CDK2 <Reference id=26619/>, It is 25-fold selective for CDKs 1 and 2 over CDK4. BMS-265246 was a preclinical lead compound.
iupac name: (4-butoxy-1H-pyrazolo[3,4-b]pyridin-5-yl)-(2,6-difluoro-4-methylphenyl)methanone
xref: CHEMBL310840
synonym: BMS265246
synonym: BMS 265246
approved: f
ligand name: BMS-265246
type: SyntheticOrganicLigand

PF-4800567
in ch i key: AUMDBEHGJRZSOO-UHFFFAOYSA-N
in ch i: InChI=1S/C17H18ClN5O2/c18-11-2-1-3-13(8-11)25-9-14-15-16(19)20-10-21-17(15)23(22-14)12-4-6-24-7-5-12/h1-3,8,10,12H,4-7,9H2,(H2,19,20,21)
comment: PF-4800567 is an inhibitor of the casein kinase, CK1ε <Reference id=26618/>. It was a preclinical lead compound.
iupac name: 3-[(3-chlorophenoxy)methyl]-1-(oxan-4-yl)pyrazolo[3,4-d]pyrimidin-4-amine
xref: CHEMBL2069623
synonym: PF4800567
synonym: PF 4800567
approved: f
ligand name: PF-4800567
type: SyntheticOrganicLigand

HG-9-91-01
in ch i key: UYUHRKLITDJEHB-UHFFFAOYSA-N
in ch i: InChI=1S/C32H37N7O3/c1-22-7-6-8-23(2)31(22)36-32(40)39(27-14-13-26(41-4)19-28(27)42-5)30-20-29(33-21-34-30)35-24-9-11-25(12-10-24)38-17-15-37(3)16-18-38/h6-14,19-21H,15-18H2,1-5H3,(H,36,40)(H,33,34,35)
comment: HG-9-91-01 is an inhibitor of the calcium/calmodulin-dependent protein kinases (CAMKs), salt-inducible kinases 1, 2 and 3 (SIK1-3) <Reference id=26617/>.
iupac name: 1-(2,4-dimethoxyphenyl)-3-(2,6-dimethylphenyl)-1-[6-[4-(4-methylpiperazin-1-yl)anilino]pyrimidin-4-yl]urea
synonym: HY-15776
approved: f
ligand name: HG-9-91-01
type: SyntheticOrganicLigand

CRT 0066101
canonical SMILES: CCC(CNc1ccnc(n1)c1cc(ccc1O)c1cnn(c1)C)N
in ch i key: SCJXQZZYGYLKJG-CQSZACIVSA-N
in ch i: InChI=1S/C18H22N6O/c1-3-14(19)10-21-17-6-7-20-18(23-17)15-8-12(4-5-16(15)25)13-9-22-24(2)11-13/h4-9,11,14,25H,3,10,19H2,1-2H3,(H,20,21,23)/t14-/m1/s1
comment: CRT 0066101 is a potent and selective protein kinase D inhibitor <Reference id=26616/>. It was tested in preclinical studies. The structure represented here was drawn from <Reference id=26616/>. PubChem CID 76844479 represents an alternative tautomer of this compound.
iupac name: 2-[4-[[(2R)-2-Aminobutyl]amino]pyrimidin-2-yl]-4-(1-methyl-1H-pyrazol-4-yl)phenol dihydrochloride
approved: f
ligand name: CRT 0066101
type: SyntheticOrganicLigand

WZ4003
in ch i key: SDGJBAUIGHSMRI-UHFFFAOYSA-N
in ch i: InChI=1S/C25H29ClN6O3/c1-4-23(33)28-17-6-5-7-19(14-17)35-24-20(26)16-27-25(30-24)29-21-9-8-18(15-22(21)34-3)32-12-10-31(2)11-13-32/h5-9,14-16H,4,10-13H2,1-3H3,(H,28,33)(H,27,29,30)
comment: WZ4003 is a selective inhibitor of the AMP-activated protein kinases, NUAK1 and NUAK2 <Reference id=26615/>. N.B. compare to <Ligand id=8977/> which is selective for NUAK1. HTH-01-015 and WZ4003 can be used as chemical probes to delineate the biological roles of the NUAK kinases.
iupac name: N-[3-[5-chloro-2-[2-methoxy-4-(4-methylpiperazin-1-yl)anilino]pyrimidin-4-yl]oxyphenyl]propanamide
synonym: WZ-4003
approved: f
ligand name: WZ4003
type: SyntheticOrganicLigand

OTSSP167
in ch i key: WZJUACDPTWDYSI-UHFFFAOYSA-N
comment: OTSSP167 is an orally available inhibitor of the protein kinase, maternal embryonic leucine zipper kinase (MELK) <Reference id=26614/>. This inhibitor has multiple off-targets.
synonym: OTSSP 167
synonym: OTSSP-167
synonym: AMX10201
approved: f
ligand name: OTSSP167
type: SyntheticOrganicLigand

PF-3644022
in ch i key: CMWRPDHVGMHLSZ-GFCCVEGCSA-N
in ch i: InChI=1S/C21H18N4OS/c1-11-3-4-13(10-22-11)15-6-5-14-16(25-15)7-8-17-18(14)19-20(27-17)21(26)24-12(2)9-23-19/h3-8,10,12,23H,9H2,1-2H3,(H,24,26)/t12-/m1/s1
comment: PF-3644022 is an experimental inhibitor of the protein kinase, mitogen-activated protein kinase-activated protein kinase 2 (MAPKAPK2) <Reference id=26613/>. It is orally bioavailable and was tested in preclinical studies.
iupac name: (15R)-15-methyl-5-(6-methylpyridin-3-yl)-11-thia-6,14,17-triazatetracyclo[8.8.0.0^{2,7}.0^{12,18}]octadeca-1(10),2,4,6,8,12(18)-hexaen-13-one
xref: CHEMBL1231206
synonym: PF3644022
synonym: PF 3644022
approved: f
ligand name: PF-3644022
type: SyntheticOrganicLigand

CCT241533
isomeric SMILES: COc1cc2[nH]/c(=C/3/C=C(F)C=CC3=O)/nc(c2cc1OC)N[C@@H]1CNC[C@H]1C(O)(C)C
in ch i key: IXTQNANZDPZION-GSOOIIRJSA-N
in ch i: InChI=1S/C23H27FN4O4/c1-23(2,30)15-10-25-11-17(15)27-21-13-8-19(31-3)20(32-4)9-16(13)26-22(28-21)14-7-12(24)5-6-18(14)29/h5-9,15,17,25-26,30H,10-11H2,1-4H3,(H,27,28)/b22-14-/t15-,17-/m1/s1
comment: CCT241533 is a Type-1 inhibitor of the protein kinase CHK2 <Reference id=26612/>. This compound has been assessed in preclinical investigations.
iupac name: (6Z)-4-fluoro-6-[4-[[(3S,4R)-4-(2-hydroxypropan-2-yl)pyrrolidin-3-yl]amino]-6,7-dimethoxy-1H-quinazolin-2-ylidene]cyclohexa-2,4-dien-1-one
synonym: CCT-241533
synonym: CCT 241533
approved: f
ligand name: CCT241533
type: SyntheticOrganicLigand

PF-477736
in ch i key: YFNWWNRZJGMDBR-LJQANCHMSA-N
in ch i: InChI=1S/C22H25N7O2/c1-29-11-13(9-25-29)20-16-10-24-28-21(30)15-7-14(8-17(27-20)18(15)16)26-22(31)19(23)12-5-3-2-4-6-12/h7-12,19,24H,2-6,23H2,1H3,(H,26,31)(H,28,30)/t19-/m1/s1
comment: PF-477736 <Reference id=26603/> is an inhibitor that can be used as a tool compound to study the activity of the CAMK family protein kinase CHK1. Secondary, off-targets include VEGFR2, FMS and YES protein kinases.
synonym: PF 477736
synonym: PF477736
synonym: PF 00477736
synonym: PF-00477736
approved: f
ligand name: PF-477736
type: SyntheticOrganicLigand

VE-821
in ch i key: DUIHHZKTCSNTGM-UHFFFAOYSA-N
in ch i: InChI=1S/C18H16N4O3S/c1-26(24,25)14-9-7-12(8-10-14)15-11-20-17(19)16(22-15)18(23)21-13-5-3-2-4-6-13/h2-11H,1H3,(H2,19,20)(H,21,23)
comment: VE-821 <Reference id=26602/> is an inhibitor of the atypical protein kinase ATR.
iupac name: 3-amino-6-(4-methylsulfonylphenyl)-N-phenylpyrazine-2-carboxamide
xref: CHEMBL1766779
synonym: VE 821
approved: f
ligand name: VE-821
type: SyntheticOrganicLigand

KU-60019
in ch i key: SCELLOWTHJGVIC-BGYRXZFFSA-N
in ch i: InChI=1S/C30H33N3O5S/c1-19-16-32(17-20(2)37-19)18-28(35)31-23-6-7-27-22(13-23)12-21-4-3-5-25(30(21)39-27)26-14-24(34)15-29(38-26)33-8-10-36-11-9-33/h3-7,13-15,19-20H,8-12,16-18H2,1-2H3,(H,31,35)/t19-,20+
comment: KU-60019 <Reference id=26601/> is an inhibitor that can be used as a tool compound to study the activity of the atypical protein kinase ATM. Known off-target inhibition has been determined for the β, γ and δ PI3 kinases.
iupac name: 2-[(2S,6R)-2,6-dimethylmorpholin-4-yl]-N-[5-(6-morpholin-4-yl-4-oxopyran-2-yl)-9H-thioxanthen-2-yl]acetamide
xref: CHEMBL2140173
approved: f
ligand name: KU-60019
type: SyntheticOrganicLigand

GSK650394
in ch i key: WVSBGSNVCDAMCF-UHFFFAOYSA-N
in ch i: InChI=1S/C25H22N2O2/c28-25(29)20-11-10-18(12-21(20)17-8-4-5-9-17)23-15-27-24-22(23)13-19(14-26-24)16-6-2-1-3-7-16/h1-3,6-7,10-15,17H,4-5,8-9H2,(H,26,27)(H,28,29)
comment: GSK650394 <Reference id=26600/> is an inhibitor of the AGC protein kinases SGK1 and SGK2.
iupac name: 2-cyclopentyl-4-(5-phenyl-1H-pyrrolo[2,3-b]pyridin-3-yl)benzoic acid
xref: CHEMBL558642
synonym: GSK 650394
synonym: GSK-650394
approved: f
ligand name: GSK650394
type: SyntheticOrganicLigand

tranexamic acid
canonical SMILES: NCC1CCC(CC1)C(=O)O
isomeric SMILES: NC[C@@H]1CC[C@H](CC1)C(=O)O
in ch i key: GYDJEQRTZSCIOI-LJGSYFOKSA-N
in ch i: InChI=1S/C8H15NO2/c9-5-6-1-3-7(4-2-6)8(10)11/h6-7H,1-5,9H2,(H,10,11)/t6-,7-
comment: This ligand is represented on PubChem without specified stereochemistry by CID 5526.
iupac name: trans-4-(Aminomethyl)cyclohexanecarboxylic acid
xref: CHEMBL877
synonym: Amcha
synonym: Amikapron
synonym: Amstat
synonym: Anvitoff
synonym: Carxamin
synonym: Cyclocapron
synonym: Emorhalt
synonym: Frenolyse
synonym: Mastop
synonym: Rikavarin
synonym: Rikavarin-S
synonym: Tamcha
synonym: Tranexan
synonym: Transamin
synonym: Trasamlon
synonym: Ugurol
synonym: Cyklokapron®
synonym: CL-65336
synonym: trans AMCHA
synonym: Cyclo-F®
synonym: Femstrual®
synonym: Lysteda®
approved: t
ligand name: tranexamic acid
type: SyntheticOrganicLigand

BIX 02565
in ch i key: ZHMXXVNQAFCXKK-QGZVFWFLSA-N
in ch i: InChI=1S/C26H30N6O2/c1-17-11-12-27-25(34)23-15-18-9-10-19(16-22(18)32(17)23)24(33)29-26-28-20-7-4-5-8-21(20)31(26)14-6-13-30(2)3/h4-5,7-10,15-17H,6,11-14H2,1-3H3,(H,27,34)(H,28,29,33)/t17-/m1/s1
comment: BIX 02565 <Reference id=26599/> is an inhibitor that can be used as a tool compound to study the activity of the AGC family protein kinase RSK2. Known off-target effects have been determined against LRRK2, PRKD1/2/3 and RET kinases.
iupac name: (5R)-N-[1-[3-(dimethylamino)propyl]benzimidazol-2-yl]-5-methyl-1-oxo-2,3,4,5-tetrahydro-[1,4]diazepino[1,2-a]indole-8-carboxamide
xref: CHEMBL1933288
synonym: BIX02565
synonym: BIX-02565
approved: f
ligand name: BIX 02565
type: SyntheticOrganicLigand

BI-D1870
in ch i key: DTEKTGDVSARYDS-UHFFFAOYSA-N
in ch i: InChI=1S/C19H23F2N5O2/c1-10(2)5-6-26-11(3)18(28)25(4)15-9-22-19(24-17(15)26)23-12-7-13(20)16(27)14(21)8-12/h7-11,27H,5-6H2,1-4H3,(H,22,23,24)
comment: BI-D1870 <Reference id=26598/> is a pan-inhibitor of RSK protein kinases. BI-D1870 has some off-target activity against the MST2 protein kinase.
iupac name: 2-(3,5-difluoro-4-hydroxyanilino)-5,7-dimethyl-8-(3-methylbutyl)-7H-pteridin-6-one
xref: CHEMBL573107
approved: f
ligand name: BI-D1870
type: SyntheticOrganicLigand

GSK269962A
in ch i key: YOVNFNXUCOWYSG-UHFFFAOYSA-N
in ch i: InChI=1S/C29H30N8O5/c1-2-37-24-17-25(31-18-23(24)33-28(37)26-27(30)35-42-34-26)41-22-5-3-4-20(16-22)32-29(38)19-6-8-21(9-7-19)40-15-12-36-10-13-39-14-11-36/h3-9,16-18H,2,10-15H2,1H3,(H2,30,35)(H,32,38)
comment: GSK269962A <Reference id=26597/> is an inhibitor that can be used as a tool compound to study the activity of the AGC family protein kinases ROCK1 and ROCK2. GSK269962A has some off-target activity against the protein kinases MSK1 and RSK1.
iupac name: N-[3-[2-(4-amino-1,2,5-oxadiazol-3-yl)-1-ethylimidazo[5,4-d]pyridin-6-yl]oxyphenyl]-4-(2-morpholin-4-ylethoxy)benzamide
xref: CHEMBL220241
synonym: GSK-269962A
synonym: GSK269962
synonym: GSK-269962
synonym: GSK 269962
synonym: aminofurazanyl-azabenzimidazole 6n
approved: f
ligand name: GSK269962A
type: SyntheticOrganicLigand

PF-4708671
in ch i key: FBLPQCAQRNSVHB-UHFFFAOYSA-N
in ch i: InChI=1S/C19H21F3N6/c1-2-13-10-23-12-24-18(13)28-7-5-27(6-8-28)11-17-25-15-4-3-14(19(20,21)22)9-16(15)26-17/h3-4,9-10,12H,2,5-8,11H2,1H3,(H,25,26)
comment: PF-4708671 <Reference id=26596/> is an inhibitor that can be used as a tool compound to study the activity of the AGC family protein kinase RPS6KB1 (p70S6K). PF-4708671 has some off-target activity against MSK1.
iupac name: 2-[[4-(5-ethylpyrimidin-4-yl)piperazin-1-yl]methyl]-6-(trifluoromethyl)-1H-benzimidazole
xref: CHEMBL2134202
synonym: PF4708671
synonym: PF 4708671
approved: f
ligand name: PF-4708671
type: SyntheticOrganicLigand

levobetaxolol
canonical SMILES: OC(COc1ccc(cc1)CCOCC1CC1)CNC(C)C
isomeric SMILES: O[C@H](COc1ccc(cc1)CCOCC1CC1)CNC(C)C
in ch i key: NWIUTZDMDHAVTP-KRWDZBQOSA-N
in ch i: InChI=1S/C18H29NO3/c1-14(2)19-11-17(20)13-22-18-7-5-15(6-8-18)9-10-21-12-16-3-4-16/h5-8,14,16-17,19-20H,3-4,9-13H2,1-2H3/t17-/m0/s1
comment: This is the active isomer of <Ligand id=549/> <Reference id=26528/>. The clinically used compound is levobetaxolol hydrochloride (PubChem CID 60656).
iupac name: (2S)-1-[4-[2-(cyclopropylmethoxy)ethyl]phenoxy]-3-(propan-2-ylamino)propan-2-ol
xref: CHEMBL1201274
synonym: (-)-betaxolol
synonym: (S)-betaxolol
synonym: AL-1577A
synonym: Betaxon®
approved: t
ligand name: levobetaxolol
type: SyntheticOrganicLigand

CCG-203920
canonical SMILES: COCCn1c(=O)sn(c1=O)CC
isomeric SMILES: COCCn1c(=O)sn(c1=O)CC
in ch i key: NCTIMJFWDQCLDW-UHFFFAOYSA-N
in ch i: InChI=1S/C7H12N2O3S/c1-3-9-6(10)8(4-5-12-2)7(11)13-9/h3-5H2,1-2H3
comment: CCG-203920 (formerly RGS4 inhibitor 13) is a potent small molecule inhibitor of regulator of G-protein signaling protein 4 (RGS4) <Reference id=26503/>
iupac name: 2-ethyl-4-(2-methoxyethyl)-1,2,4-thiadiazolidine-3,5-dione
xref: CHEMBL2037369
synonym: CCG203920
synonym: RGS4 inhibitor 13
approved: f
ligand name: CCG-203920
type: SyntheticOrganicLigand

RGS4 inhibitor 11b
canonical SMILES: CCCCn1c(=O)sn(c1=O)CC
isomeric SMILES: CCCCn1c(=O)sn(c1=O)CC
in ch i key: WTFFYZGCISALRI-UHFFFAOYSA-N
in ch i: InChI=1S/C8H14N2O2S/c1-3-5-6-9-7(11)10(4-2)13-8(9)12/h3-6H2,1-2H3
comment: This compound is a potent small molecule inhibitor of regulator of G-protein signaling protein 4 (RGS4) <Reference id=26503/>.
iupac name: 4-butyl-2-ethyl-1,2,4-thiadiazolidine-3,5-dione
xref: CHEMBL24773
synonym: thiadiazolidinone (TDZD) deriv. 6
approved: f
ligand name: RGS4 inhibitor 11b
type: SyntheticOrganicLigand

amifampridine
canonical SMILES: Nc1cnccc1N
isomeric SMILES: Nc1cnccc1N
in ch i key: OYTKINVCDFNREN-UHFFFAOYSA-N
in ch i: InChI=1S/C5H7N3/c6-4-1-2-8-3-5(4)7/h1-3H,7H2,(H2,6,8)
comment: Amifampridine is a potassium channel blocker.
iupac name: pyridine-3,4-diamine
xref: CHEMBL354077
synonym: 3,4-diaminopyridine
synonym: Firdapse®
synonym: Zenas®
synonym: 3,4-DAP
synonym: Ruzurgi®
approved: t
ligand name: amifampridine
type: SyntheticOrganicLigand

L-739,750
in ch i key: SIEXHGZWGJLLAC-OSTWSGHESA-N
in ch i: InChI=1S/C23H39N3O6S2/c1-4-16(2)20(25-13-18(24)15-33)14-32-21(12-17-8-6-5-7-9-17)22(27)26-19(23(28)29)10-11-34(3,30)31/h5-9,16,18-21,25,33H,4,10-15,24H2,1-3H3,(H,26,27)(H,28,29)/t16-,18+,19-,20+,21-/m0/s1
comment: The discovery of L-739,750 is described in <Reference id=26484/>. L-739,750 is a peptidomimetic farnesyltransferase inhibitor (FTI). Experimentally the compound is administered as a methyl ester prodrug (L-739,749) <Reference id=26484/>.
iupac name: (2S)-2-[[(2S)-2-[(2S,3S)-2-[[(2R)-2-amino-3-sulfanylpropyl]amino]-3-methylpentoxy]-3-phenylpropanoyl]amino]-4-methylsulfonylbutanoic acid
synonym: L 739750
approved: f
ligand name: L-739,750
type: SyntheticOrganicLigand

LB42708
in ch i key: GUUIRIMAQGOLHT-UHFFFAOYSA-N
in ch i: InChI=1S/C30H27BrN4O2/c31-24-10-8-22(9-11-24)17-35-21-32-16-25(35)18-33-19-28(27-7-3-5-23-4-1-2-6-26(23)27)29(20-33)30(36)34-12-14-37-15-13-34/h1-11,16,19-21H,12-15,17-18H2
comment: LB42708 is a highly potent, selective, and non-peptidic farnesyltransferase inhibitor (FTI). It has a similar chemical structure to <Ligand id=8028/>.
iupac name: [1-[[3-[(4-bromophenyl)methyl]imidazol-4-yl]methyl]-4-naphthalen-1-ylpyrrol-3-yl]-morpholin-4-ylmethanone
approved: f
ligand name: LB42708
type: SyntheticOrganicLigand

LB42908
in ch i key: VZWZHIJGBPHRDI-UHFFFAOYSA-N
in ch i: InChI=1S/C32H33N5O3/c1-34-11-13-36(14-12-34)32(38)29-20-35(19-28(29)27-8-4-6-24-5-2-3-7-26(24)27)18-25-16-33-21-37(25)17-23-9-10-30-31(15-23)40-22-39-30/h2-10,15-16,19-21,30-31H,11-14,17-18,22H2,1H3
comment: The discovery of LB42908 is described in <Reference id=26481/>, where it is compound 2. LB42908 is a highly potent, selective, and non-peptidic farnesyltransferase inhibitor (FTI). LB42908 does not appear to have progressed beyond preclinical investigation.
iupac name: 1-(1-{[1-(3a,7a-dihydro-2H-1,3-benzodioxol-5-ylmethyl)-1H-imidazol-5-yl]methyl}-4-(naphthalen-1-yl)-1H-pyrrole-3-carbonyl)-4-methylpiperazine
synonym: LB 42908
approved: f
ligand name: LB42908
type: SyntheticOrganicLigand

AZD3409
in ch i key: GIJNHMGFNKZBIR-URORMMCBSA-N
comment: AZD3409 is an an orally active double prodrug, peptidomimetic type farnesyltransferase inhibitor (FTI). It is a double prodrug in that it has its thiol and carboxylate groups blocked to reduce toxicity.
iupac name: propan-2-yl (2S)-2-[1-[2-(2-fluoroethyl)-5-[[(2S,5S)-5-(pyridine-3-carbonylsulfanyl)pyrrolidin-2-yl]methylamino]phenyl]ethenylamino]-4-methylsulfanylbutanoate
synonym: AZD 3409
synonym: AZD-3409
approved: f
ligand name: AZD3409
type: SyntheticOrganicLigand

BMS-214662
in ch i key: OLCWFLWEHWLBTO-HSZRJFAPSA-N
in ch i: InChI=1S/C25H23N5O2S2/c26-13-20-8-9-24-21(11-20)15-30(34(31,32)25-7-4-10-33-25)23(12-19-5-2-1-3-6-19)17-29(24)16-22-14-27-18-28-22/h1-11,14,18,23H,12,15-17H2,(H,27,28)/t23-/m1/s1
comment: BMS-214662 is a non-peptidomimetic competitive farnesyltransferase inhibitor (FTI) <Reference id=26476/>.
iupac name: (3R)-1-(3H-imidazol-4-ylmethyl)-3-(phenylmethyl)-4-thiophen-2-ylsulfonyl-3,5-dihydro-2H-1,4-benzodiazepine-7-carbonitrile
xref: CHEMBL351706
synonym: BMS 214662
synonym: BVM
synonym: BMS214662
approved: f
ligand name: BMS-214662
type: SyntheticOrganicLigand

tipifarnib
in ch i key: PLHJCIYEEKOWNM-HHHXNRCGSA-N
in ch i: InChI=1S/C27H22Cl2N4O/c1-32-16-31-15-25(32)27(30,18-6-9-20(28)10-7-18)19-8-11-24-23(13-19)22(14-26(34)33(24)2)17-4-3-5-21(29)12-17/h3-16H,30H2,1-2H3/t27-/m1/s1
comment: Tipifarnib is a non-peptidomimetic competitive farnesyltransferase inhibitor (FTI) <Reference id=26473/>.
iupac name: 6-[(R)-amino-(4-chlorophenyl)-(3-methylimidazol-4-yl)methyl]-4-(3-chlorophenyl)-1-methylquinolin-2-one
xref: CHEMBL289228
synonym: R115777
synonym: R-115777
synonym: Zarnestra
approved: f
ligand name: tipifarnib
type: SyntheticOrganicLigand

lonafarnib
in ch i key: DHMTURDWPRKSOA-RUZDIDTESA-N
comment: Lonafarnib is an orally bioavailable molecule which inhibits farnesyl protein transferase, an enzyme that is responsible for catalysing the transfer of a 15-carbon isoprenoid group to a variety of cellular proteins including RAS <Reference id=26464/>.
iupac name: 4-[2-[4-[(11R)-3,10-dibromo-8-chloro-6,11-dihydro-5H-benzo[1,2]cyclohepta[2,4-b]pyridin-11-yl]piperidin-1-yl]-2-oxoethyl]piperidine-1-carboxamide
xref: CHEMBL298734
synonym: SCH 66336
synonym: SCH-66336
synonym: SCH66336
synonym: Sarasar
synonym: Zokinvy®
approved: t
ligand name: lonafarnib
type: SyntheticOrganicLigand

6H05
in ch i key: WEEYMZOUPNIHLG-UHFFFAOYSA-N
comment: This compound exists in the trifluoroacetic acid form (PubChem CID 86208069). 6H05 is a selective allosteric inhibitor of oncogenic KRASG12C <Reference id=26463/>. 6H05 was used as the reference compound in the development of <Ligand id=8021/>, <Ligand id=8022/> and <Ligand id=8020/> <Reference id=26463/>.
synonym: S7330
approved: f
ligand name: 6H05
type: SyntheticOrganicLigand

K-Ras(G12C) inhibitor 9
in ch i key: ZGUSBCDCZNBNQT-UHFFFAOYSA-N
comment: This compound is a selective allosteric inhibitor of oncogenic KRASG12C <Reference id=26463/>.
iupac name: N-(1-{2-[(4-chloro-5-iodo-2-methoxyphenyl)amino]acetyl}piperidin-4-yl)ethene-1-sulfonamide
approved: f
ligand name: K-Ras(G12C) inhibitor 9
type: SyntheticOrganicLigand

K-Ras(G12C) inhibitor 6
in ch i key: XXJPOZZXKREAIA-UHFFFAOYSA-N
comment: This compound is a selective allosteric inhibitor of oncogenic KRASG12C <Reference id=26463/>.
iupac name: N-{1-[2-(2,4-dichlorophenoxy)acetyl]piperidin-4-yl}butanamide
approved: f
ligand name: K-Ras(G12C) inhibitor 6
type: SyntheticOrganicLigand

K-Ras(G12C) inhibitor 12
in ch i key: JFIFBWVNHLXJFY-UHFFFAOYSA-N
comment: This compound is as allosteric inhibitor of oncogenic KRASG12C <Reference id=26463/>.
iupac name: 1-(4-{2-[(4-chloro-2-hydroxy-5-iodophenyl)amino]acetyl}piperazin-1-yl)prop-2-en-1-one
approved: f
ligand name: K-Ras(G12C) inhibitor 12
type: SyntheticOrganicLigand

SB-415286
in ch i key: PQCXVIPXISBFPN-UHFFFAOYSA-N
in ch i: InChI=1S/C16H10ClN3O5/c17-10-7-8(5-6-12(10)21)18-14-13(15(22)19-16(14)23)9-3-1-2-4-11(9)20(24)25/h1-7,21H,(H2,18,19,22,23)
comment: SB-415286 is a potent glycogen synthase kinase-3 (GSK-3) inhibitor which is equipotent at the α and β isozymes <Reference id=26427/>.
iupac name: 3-[(3-chloro-4-hydroxyphenyl)amino]-4-(2-nitrophenyl)pyrrole-2,5-dione
xref: CHEMBL322970
synonym: SB 415286
synonym: SB415286
approved: f
ligand name: SB-415286
type: SyntheticOrganicLigand

1-azakenpaullone
canonical SMILES: O=C1Nc2cccnc2c2c(C1)c1cc(Br)ccc1[nH]2
isomeric SMILES: O=C1Nc2cccnc2c2c(C1)c1cc(Br)ccc1[nH]2
in ch i key: NTSBZVCEIVPKBJ-UHFFFAOYSA-N
in ch i: InChI=1S/C15H10BrN3O/c16-8-3-4-11-9(6-8)10-7-13(20)18-12-2-1-5-17-15(12)14(10)19-11/h1-6,19H,7H2,(H,18,20)
comment: 1-azakenpaullone is a potent and selective ATP-competitive inhibitor of glycogen synthase kinase-3β (GSK-3β) <Reference id=26438/>. In contrast to other paullones, this analogue has insignificant activity at the phylogenetically related cyclin-dependent kinases (CDKs) CDK1 and CDK5. 1-azakenpaullone is compound 16 in <Reference id=26438/>.
xref: CHEMBL336961
synonym: azakenpaullone
approved: f
ligand name: 1-azakenpaullone
type: SyntheticOrganicLigand

IM-12
in ch i key: ZKJAZFUFPPSFCO-UHFFFAOYSA-N
in ch i: InChI=1S/C22H20FN3O2/c1-13-18(16-5-3-4-6-17(16)25-13)19-20(22(28)26(2)21(19)27)24-12-11-14-7-9-15(23)10-8-14/h3-10,24-25H,11-12H2,1-2H3
comment: IM-12 is a selective inhibitor of glycogen synthase kinase-3β (GSK-3β) <Reference id=26433/>.
iupac name: 3-[2-(4-fluorophenyl)ethylamino]-1-methyl-4-(2-methyl-1H-indol-3-yl)pyrrole-2,5-dione
xref: CHEMBL1254896
approved: f
ligand name: IM-12
type: SyntheticOrganicLigand

CHIR-98014
in ch i key: MDZCSIDIPDZWKL-UHFFFAOYSA-N
comment: CHIR-98014 is a potent ATP-competitive inhibitor of glycogen synthase kinase-3α (GSK-3α) and GSK-3β <Reference id=26426/>.
iupac name: 6-N-[2-[[4-(2,4-dichlorophenyl)-5-imidazol-1-ylpyrimidin-2-yl]amino]ethyl]-3-nitropyridine-2,6-diamine
xref: CHEMBL3185148
synonym: CHIR98014
synonym: CHIR 98014
approved: f
ligand name: CHIR-98014
type: SyntheticOrganicLigand

ataluren
canonical SMILES: Fc1ccccc1c1onc(n1)c1cccc(c1)C(=O)O
isomeric SMILES: Fc1ccccc1c1onc(n1)c1cccc(c1)C(=O)O
in ch i key: OOUGLTULBSNHNF-UHFFFAOYSA-N
in ch i: InChI=1S/C15H9FN2O3/c16-12-7-2-1-6-11(12)14-17-13(18-21-14)9-4-3-5-10(8-9)15(19)20/h1-8H,(H,19,20)
comment: Ataluren is a compound in an emerging class of chemicals which induce ribosomal readthrough. This developing pharmaceutical intervention has been termed 'readthrough strategy'. Clinically, this type of compound has potential benefit in the treatment of genetic disorders associated with loss of functional protein due to nonsense or PTC mutations, such as certain types of muscular dystrophy, cystic fibrosis and many cancers <Reference id=23964/><Reference id=23963/>.
iupac name: 3-[5-(2-fluorophenyl)-1,2,4-oxadiazol-3-yl]benzoic acid
xref: CHEMBL256997
synonym: PTC124
synonym: Translarna
approved: t
ligand name: ataluren
type: SyntheticOrganicLigand

SB 216763
in ch i key: JCSGFHVFHSKIJH-UHFFFAOYSA-N
comment: SB 216763 is a potent and selective inhibitor of glycogen synthase kinase 3 (GSK-3), equipotent at GSK-3α and GSK-3β isozymes <Reference id=26427/>. The compound is an investigational tool which may be used to help clarify the role played by GSK-3 in cellular signalling.
iupac name: 3-(2,4-dichlorophenyl)-4-(1-methylindol-3-yl)pyrrole-2,5-dione
xref: CHEMBL102714
synonym: SB-216763
synonym: SB216763
approved: f
ligand name: SB 216763
type: SyntheticOrganicLigand

laduviglusib
in ch i key: AQGNHMOJWBZFQQ-UHFFFAOYSA-N
in ch i: InChI=1S/C22H18Cl2N8/c1-13-10-29-21(31-13)17-12-30-22(32-20(17)16-4-3-15(23)8-18(16)24)27-7-6-26-19-5-2-14(9-25)11-28-19/h2-5,8,10-12H,6-7H2,1H3,(H,26,28)(H,29,31)(H,27,30,32)
comment: Laduviglusib (CHIR-99021) is an ATP-competitive inhibitor of glycogen synthase kinase-3α and β (GSK-3α/β), equipotent at both isozymes <Reference id=26426/>. The chemical structure of CHIR-99021 matches that submitted to the WHO for the INN laduviglusib. GSK-3β has been implicated in multiple human disorders, by influencing a number of significant cellular pathways (including insulin signalling and glycogen synthesis, neurotrophic factor signalling, Wnt signalling, neurotransmitter signalling and microtubule dynamics) <Reference id=40206/>. CHIR-99021 acts as a functional Wnt pathway activator <Reference id=40207/><Reference id=40208/>. Zaki syndrome, a rare disorder of embryonic organ development in humans, can arise due to homozygous mutations in the Wnt ligand secretion mediator gene (WLS) <Reference id=43023/>. CHIR-99021 has been used in a mouse model of Zaki syndrome to demonstrate that activation of Wnt pathway signalling can partially restore embryonic development <Reference id=43023/>.
iupac name: 6-[2-[[4-(2,4-dichlorophenyl)-5-(5-methyl-1H-imidazol-2-yl)pyrimidin-2-yl]amino]ethylamino]pyridine-3-carbonitrile
xref: CHEMBL412142
synonym: CHIR99021
synonym: CHIR 99021
synonym: CT-99021
synonym: CT99021
synonym: CHIR-99021
approved: f
ligand name: laduviglusib
type: SyntheticOrganicLigand

PP121
in ch i key: NVRXTLZYXZNATH-UHFFFAOYSA-N
in ch i: InChI=1S/C17H17N7/c18-15-13-14(11-7-10-5-6-19-16(10)20-8-11)23-24(12-3-1-2-4-12)17(13)22-9-21-15/h5-9,12H,1-4H2,(H,19,20)(H2,18,21,22)
comment: PP121 is a multi-targeted kinase inhibitor, discovery of which is described in <Reference id=26399/>, where it is compound 6. It is designed to target tyrosine kinases and phosphatidylinositol-3 kinases (PI3Ks), a set of interconnected oncogenes, that are of intense interest as molecular targets in the drug discovery process.
iupac name: 1-cyclopentyl-3-(1H-pyrrolo[2,3-b]pyridin-5-yl)pyrazolo[3,4-d]pyrimidin-4-amine
xref: CHEMBL1081312
synonym: PP-121
synonym: PP 121
approved: f
ligand name: PP121
type: SyntheticOrganicLigand

PIK-75
isomeric SMILES: Brc1ccc2n(c1)c(/C=N/N(S(=O)(=O)c1cc(ccc1C)[N+](=O)[O-])C)cn2
in ch i key: QTHCAAFKVUWAFI-DJKKODMXSA-N
comment: The discovery of PIK-75 is described by Hayakawa et al. (2007) <Reference id=26422/>, where it is compound 8c.
iupac name: N-[(E)-(6-bromoimidazo[1,2-a]pyridin-3-yl)methylideneamino]-N,2-dimethyl-5-nitrobenzenesulfonamide
xref: CHEMBL393525
synonym: PIK75
synonym: PIK 75
synonym: imidazopyridine derivative 8c [PMID 17601739]
approved: f
ligand name: PIK-75
type: SyntheticOrganicLigand

KU-0060648
in ch i key: AATCBLYHOUOCTO-UHFFFAOYSA-N
in ch i: InChI=1S/C33H34N4O4S/c1-2-35-12-14-36(15-13-35)21-29(39)34-26-11-10-23(33-31(26)25-6-3-4-9-28(25)42-33)22-7-5-8-24-27(38)20-30(41-32(22)24)37-16-18-40-19-17-37/h3-11,20H,2,12-19,21H2,1H3,(H,34,39)
comment: KU-0060648 is a dual inhibitor of DNA dependent protein kinase (DNA-PK) and the phosphatidylinositol-4,5-bisphosphate 3-kinase (PI3K) α, β and δ subunits. This compound is an analogue of <Ligand id=8010/> with improved solubility and potency, and additional activity against PI3Ks <Reference id=25917/>. This is compound 39 in Cano et al. (2013) <Reference id=25917/>.
iupac name: 2-(4-ethylpiperazin-1-yl)-N-[4-(2-morpholin-4-yl-4-oxochromen-8-yl)dibenzothiophen-1-yl]acetamide
xref: CHEMBL1086377
synonym: KU 0060648
approved: f
ligand name: KU-0060648
type: SyntheticOrganicLigand

NU-7441
in ch i key: JAMULYFATHSZJM-UHFFFAOYSA-N
in ch i: InChI=1S/C25H19NO3S/c27-21-15-23(26-11-13-28-14-12-26)29-24-17(6-3-9-20(21)24)19-8-4-7-18-16-5-1-2-10-22(16)30-25(18)19/h1-10,15H,11-14H2
comment: NU-7441 is a potent and selective, ATP-competitive inhibitor of DNA-dependent protein kinase (DNA-PK) <Reference id=26410/>. It is compound 22g in Leahy et al. (2004) <Reference id=26410/>.
iupac name: 8-dibenzothiophen-4-yl-2-morpholin-4-ylchromen-4-one
xref: CHEMBL188678
synonym: NU7441
synonym: NU 7441
synonym: KU-57788
approved: f
ligand name: NU-7441
type: SyntheticOrganicLigand

PHT-427
canonical SMILES: CCCCCCCCCCCCc1ccc(cc1)S(=O)(=O)Nc1nncs1
isomeric SMILES: CCCCCCCCCCCCc1ccc(cc1)S(=O)(=O)Nc1nncs1
in ch i key: BYWWNRBKPCPJMG-UHFFFAOYSA-N
in ch i: InChI=1S/C20H31N3O2S2/c1-2-3-4-5-6-7-8-9-10-11-12-18-13-15-19(16-14-18)27(24,25)23-20-22-21-17-26-20/h13-17H,2-12H2,1H3,(H,22,23)
comment: PHT-427 is a novel dual inhibitor of 3-phosphoinositide dependent protein kinase 1 (PDK1) and Akt (protein kinase B) <Reference id=26408/>. The original identification of PHT-427 (compound 14) as an Akt inhibitor is described in <Reference id=26409/> where it is shown to bind to the pleckstrin homology (PH) domain of Akt, not to the catalytic ATP binding site. PDK1 activates Akt by phosphorylating Thr308 in Akt's kinase domain. The PDK1/Akt signaling pathway plays a key role in cancer cell growth, survival, and tumour angiogenesis and represents a promising target for oncology therapeutics <Reference id=26405/><Reference id=26406/>.
iupac name: 4-dodecyl-N-(1,3,4-thiadiazol-2-yl)benzenesulfonamide
xref: CHEMBL595583
synonym: PHT 427
synonym: PHT427
approved: f
ligand name: PHT-427
type: SyntheticOrganicLigand

xipamide
in ch i key: MTZBBNMLMNBNJL-UHFFFAOYSA-N
comment: Xipamide is a sulfonamide diuretic.
iupac name: 4-chloro-N-(2,6-dimethylphenyl)-2-hydroxy-5-sulfamoylbenzamide
xref: CHEMBL517199
synonym: BE-1293
synonym: MJF-10938
synonym: Diurexan®
synonym: Aquaphor
synonym: Aquaphoril
approved: t
ligand name: xipamide
type: SyntheticOrganicLigand

GSK2334470
in ch i key: QLPHOXTXAKOFMU-WBVHZDCISA-N
in ch i: InChI=1S/C25H34N8O/c1-15-8-9-17(24(34)28-18-6-4-3-5-7-18)14-33(15)22-13-20(29-25(27-2)30-22)16-10-11-19-21(12-16)31-32-23(19)26/h10-13,15,17-18H,3-9,14H2,1-2H3,(H,28,34)(H3,26,31,32)(H,27,29,30)/t15-,17+/m1/s1
comment: GSK2334470 is a novel 3-phosphoinositide dependent protein kinase 1 (PDK1) inhibitor. Its discovery is described in <Reference id=26407/>, where it is compound 28d. The PDK1/Akt signaling pathway plays a key role in cancer cell growth, survival, and tumour angiogenesis and represents a promising target for oncology therapeutics <Reference id=26405/><Reference id=26406/>.
iupac name: (3S,6R)-1-[6-(3-amino-1H-indazol-6-yl)-2-(methylamino)pyrimidin-4-yl]-N-cyclohexyl-6-methylpiperidine-3-carboxamide
xref: CHEMBL1765740
synonym: GSK-2334470
synonym: GSK 2334470
approved: f
ligand name: GSK2334470
type: SyntheticOrganicLigand

ML297
canonical SMILES: O=C(Nc1cc(nn1c1ccccc1)C)Nc1ccc(c(c1)F)F
isomeric SMILES: O=C(Nc1cc(nn1c1ccccc1)C)Nc1ccc(c(c1)F)F
in ch i key: IEKSMUSSYJUQMY-UHFFFAOYSA-N
in ch i: InChI=1S/C17H14F2N4O/c1-11-9-16(23(22-11)13-5-3-2-4-6-13)21-17(24)20-12-7-8-14(18)15(19)10-12/h2-10H,1H3,(H2,20,21,24)
iupac name: 1-(3,4-difluorophenyl)-3-(5-methyl-2-phenylpyrazol-3-yl)urea
xref: CHEMBL2409106
synonym: ML-297
synonym: ML 297
approved: f
ligand name: ML297
type: SyntheticOrganicLigand

BX-912
in ch i key: DMMILYKXNCVKOJ-UHFFFAOYSA-N
in ch i: InChI=1S/C20H23BrN8O/c21-17-12-24-19(28-18(17)23-7-6-16-11-22-13-25-16)26-14-4-3-5-15(10-14)27-20(30)29-8-1-2-9-29/h3-5,10-13H,1-2,6-9H2,(H,22,25)(H,27,30)(H2,23,24,26,28)
comment: BX-912 is a potent, ATP-competitive and specific inhibitor of 3-phosphoinositide dependent protein kinase 1 (PDK1). The discovery of BX-912 is described in <Reference id=26403/> and is covered by patent WO2004048343 <Reference id=26404/>. The PDK1/Akt signaling pathway plays a key role in cancer cell growth, survival, and tumour angiogenesis and represents a promising target for oncology therapeutics <Reference id=26405/><Reference id=26406/>.
iupac name: N-[3-[[5-bromo-4-[2-(3H-imidazol-4-yl)ethylamino]pyrimidin-2-yl]amino]phenyl]pyrrolidine-1-carboxamide
synonym: BX 912
synonym: BX912
approved: f
ligand name: BX-912
type: SyntheticOrganicLigand

OSU-03012
in ch i key: YULUCECVQOCQFQ-UHFFFAOYSA-N
in ch i: InChI=1S/C26H19F3N4O/c27-26(28,29)24-14-23(33(32-24)20-10-8-19(9-11-20)31-25(34)15-30)18-7-12-22-17(13-18)6-5-16-3-1-2-4-21(16)22/h1-14H,15,30H2,(H,31,34)
comment: OSU-03012 is a potent inhibitor of recombinant 3-phosphoinositide dependent protein kinase 1 (PDK1). Its discovery is described in <Reference id=26402/>, where it is compound 34. The PDK1/Akt signaling pathway plays a key role in cancer cell growth, survival, and tumour angiogenesis and represents a promising target for oncology therapeutics <Reference id=26405/><Reference id=26406/>.
iupac name: 2-amino-N-[4-[5-phenanthren-2-yl-3-(trifluoromethyl)pyrazol-1-yl]phenyl]acetamide
xref: CHEMBL1650595
synonym: OSU03012
synonym: AR-12
approved: f
ligand name: OSU-03012
type: SyntheticOrganicLigand

torin 1
in ch i key: AKCRNFFTGXBONI-UHFFFAOYSA-N
in ch i: InChI=1S/C35H28F3N5O2/c1-2-32(44)42-15-13-41(14-16-42)31-11-9-26(19-28(31)35(36,37)38)43-33(45)12-8-24-20-40-30-10-7-22(18-27(30)34(24)43)25-17-23-5-3-4-6-29(23)39-21-25/h3-12,17-21H,2,13-16H2,1H3
comment: Torin 1 is a potent inhibitor of mTOR in both mTOR containing protein complexes, mTORC1 and mTORC2. The discovery of torin 1 is described in <Reference id=26400/>, where it is compound 37.
iupac name: 1-[4-(4-propanoylpiperazin-1-yl)-3-(trifluoromethyl)phenyl]-9-quinolin-3-ylbenzo[h][1,6]naphthyridin-2-one
xref: CHEMBL1256459
synonym: Torin-1
synonym: Torin1
approved: f
ligand name: torin 1
type: SyntheticOrganicLigand

berzosertib
in ch i key: JZCWLJDSIRUGIN-UHFFFAOYSA-N
in ch i: InChI=1S/C24H25N5O3S/c1-15(2)33(30,31)19-10-8-18(9-11-19)21-14-27-24(25)23(28-21)22-12-20(29-32-22)17-6-4-16(5-7-17)13-26-3/h4-12,14-15,26H,13H2,1-3H3,(H2,25,27)
comment: Berzosertib (VE-822) is a potent and selective inhibitor of the serine/threonine kinase ATR <Reference id=37569/>. The structure of VE-822 is claimed in patent US20130089626 <Reference id=26397/>. VE-822 is under investigated for its potential antineoplastic action <Reference id=26398/><Reference id=39779/>.
iupac name: 3-[3-[4-(methylaminomethyl)phenyl]-1,2-oxazol-5-yl]-5-(4-propan-2-ylsulfonylphenyl)pyrazin-2-amine
synonym: VE-822
synonym: VE 822
synonym: VX-970
synonym: VX970
synonym: M6620
approved: f
ligand name: berzosertib
type: SyntheticOrganicLigand

SQ-109
canonical SMILES: CC(=CCNCCNC1C2CC3CC1CC(C2)C3)CCC=C(C)C
in ch i key: JFIBVDBTCDTBRH-REZTVBANSA-N
in ch i: InChI=1S/C22H38N2/c1-16(2)5-4-6-17(3)7-8-23-9-10-24-22-20-12-18-11-19(14-20)15-21(22)13-18/h5,7,18-24H,4,6,8-15H2,1-3H3/b17-7+
comment: SQ-109 is a [1,2]-diamine-based ethambutol analogue included in the Medicines for Malaria Pandemic Response Box (MMV PRB). Functionally, it inhibits Mycobacterial membrane protein large 3 (MmpL3) and has advanced to clinical evaluation for the treatment of tuberculosis <Reference id=41940/>. The compound also has antimalarial activity. The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
iupac name: N'-(2-adamantyl)-N-[(2E)-3,7-dimethylocta-2,6-dienyl]ethane-1,2-diamine
xref: CHEMBL561057
synonym: SQ 109
synonym: SQ109
synonym: MMV687273
approved: f
ligand name: SQ-109
type: SyntheticOrganicLigand

6-fluoromevalonate pyrophosphate
canonical SMILES: FCC(CC(=O)O)(CCOP(=O)(OP(=O)(O)O)O)O
isomeric SMILES: FC[C@](CC(=O)O)(CCOP(=O)(OP(=O)(O)O)O)O
in ch i key: YIGLDWRZXXHIGZ-ZCFIWIBFSA-N
in ch i: InChI=1S/C6H13FO10P2/c7-4-6(10,3-5(8)9)1-2-16-19(14,15)17-18(11,12)13/h10H,1-4H2,(H,8,9)(H,14,15)(H2,11,12,13)/t6-/m1/s1
comment: Close analogue of <Ligand id=3205/>.
iupac name: (3R)-3-(fluoromethyl)-3-hydroxy-5-[hydroxy(phosphonooxy)phosphoryl]oxypentanoic acid
xref: CHEMBL1160328
synonym: 6-FMevPP
approved: f
ligand name: 6-fluoromevalonate pyrophosphate
type: SyntheticOrganicLigand

compound 3 [Dreyer et al., 1991]
in ch i key: XKZCNQAYFRBCKR-HNNXBMFYSA-N
in ch i: InChI=1S/C19H21Cl2O6P/c20-14-8-17(21)16(6-7-28(25,26)12-15(22)10-19(23)24)18(9-14)27-11-13-4-2-1-3-5-13/h1-5,8-9,15,22H,6-7,10-12H2,(H,23,24)(H,25,26)/t15-/m0/s1
comment: This ligand is referred to as compound 3 in the reference <Reference id=26362/>, for which no PMID is available. It is an HMG-CoA reductase inhibitor.
iupac name: (3S)-4-[2-(2,4-dichloro-6-phenylmethoxyphenyl)ethyl-hydroxyphosphoryl]-3-hydroxybutanoic acid
xref: CHEMBL39102
approved: f
ligand name: compound 3 [Dreyer et al., 1991]
type: SyntheticOrganicLigand

compound 2 [Dreyer et al., 1991]
in ch i key: VWKZOIOUHUHQKZ-HZPDHXFCSA-N
in ch i: InChI=1S/C20H22Cl2O5/c21-14-8-18(22)17(7-6-15(23)10-16(24)11-20(25)26)19(9-14)27-12-13-4-2-1-3-5-13/h1-5,8-9,15-16,23-24H,6-7,10-12H2,(H,25,26)/t15-,16-/m1/s1
comment: This ligand is referred to as compound 2 in the reference Dreyer et al., 1991 <Reference id=26362/>, for which no PMID is available.
iupac name: (3R,5R)-7-(2,4-dichloro-6-phenylmethoxyphenyl)-3,5-dihydroxyheptanoic acid
xref: CHEMBL39312
approved: f
ligand name: compound 2 [Dreyer et al., 1991]
type: SyntheticOrganicLigand

isoferulic acid
canonical SMILES: COc1ccc(cc1O)C=CC(=O)O
isomeric SMILES: COc1ccc(cc1O)/C=C/C(=O)O
in ch i key: QURCVMIEKCOAJU-HWKANZROSA-N
in ch i: InChI=1S/C10H10O4/c1-14-9-4-2-7(6-8(9)11)3-5-10(12)13/h2-6,11H,1H3,(H,12,13)/b5-3+
iupac name: 3-(3-hydroxy-4-methoxyphenyl)prop-2-enoic acid
xref: CHEMBL233295
approved: f
ligand name: isoferulic acid
type: SyntheticOrganicLigand

BPH-676
in ch i key: NWIARQRYIRVYCM-UHFFFAOYSA-N
in ch i: InChI=1S/C20H20O8P2/c21-20(29(22,23)24,30(25,26)27)14-28-19-11-5-10-18(13-19)17-9-4-8-16(12-17)15-6-2-1-3-7-15/h1-13,21H,14H2,(H2,22,23,24)(H2,25,26,27)
iupac name: [1-hydroxy-2-[3-(3-phenylphenyl)phenoxy]-1-phosphonoethyl]phosphonic acid
xref: CHEMBL260880
synonym: BPH 676
synonym: BPH676
approved: f
ligand name: BPH-676
type: SyntheticOrganicLigand

BPH-608
in ch i key: YXQQNSYZOQHKHD-UHFFFAOYSA-N
in ch i: InChI=1S/C20H20O7P2/c21-20(28(22,23)24,29(25,26)27)14-15-6-4-9-17(12-15)19-11-5-10-18(13-19)16-7-2-1-3-8-16/h1-13,21H,14H2,(H2,22,23,24)(H2,25,26,27)
iupac name: [1-hydroxy-2-[3-(3-phenylphenyl)phenyl]-1-phosphonoethyl]phosphonic acid
xref: CHEMBL213490
synonym: BPH608
synonym: BPH 608
approved: f
ligand name: BPH-608
type: SyntheticOrganicLigand

BPH-629
in ch i key: BYVXAUZOTGITQZ-UHFFFAOYSA-N
in ch i: InChI=1S/C20H18O8P2/c21-20(29(22,23)24,30(25,26)27)12-13-5-3-6-14(11-13)15-8-4-9-17-16-7-1-2-10-18(16)28-19(15)17/h1-11,21H,12H2,(H2,22,23,24)(H2,25,26,27)
iupac name: [2-(3-dibenzofuran-4-ylphenyl)-1-hydroxy-1-phosphonoethyl]phosphonic acid
xref: CHEMBL411274
synonym: BPH 629
synonym: BPH629
approved: f
ligand name: BPH-629
type: SyntheticOrganicLigand

BPH-675
in ch i key: MZVWVRVNMXTDAK-UHFFFAOYSA-N
in ch i: InChI=1S/C24H23NO9P2S/c26-24(35(27,28)29,36(30,31)32)16-17-5-3-8-19(13-17)20-9-4-10-22(14-20)25-37(33,34)23-12-11-18-6-1-2-7-21(18)15-23/h1-15,25-26H,16H2,(H2,27,28,29)(H2,30,31,32)
iupac name: [1-hydroxy-2-[3-[3-(naphthalen-2-ylsulfonylamino)phenyl]phenyl]-1-phosphonoethyl]phosphonic acid
xref: CHEMBL259026
synonym: BPH675
synonym: BPH 675
approved: f
ligand name: BPH-675
type: SyntheticOrganicLigand

zotarolimus
in ch i key: CGTADGCBEXYWNE-JUKNQOCSSA-N
in ch i: InChI=1S/C52H79N5O12/c1-31-16-12-11-13-17-32(2)43(65-8)28-39-21-19-37(7)52(64,69-39)49(61)50(62)56-23-15-14-18-41(56)51(63)68-44(34(4)26-38-20-22-40(45(27-38)66-9)57-30-53-54-55-57)29-42(58)33(3)25-36(6)47(60)48(67-10)46(59)35(5)24-31/h11-13,16-17,25,30-31,33-35,37-41,43-45,47-48,60,64H,14-15,18-24,26-29H2,1-10H3/b13-11+,16-12+,32-17+,36-25+/t31-,33-,34-,35-,37-,38+,39+,40+,41+,43+,44+,45-,47-,48+,52-/m1/s1
comment: Zotarolimus (ABT-578) is an analogue of rapamycin (<Ligand id=6031/>). This compound was developed to be used in intravascular stents designed to elute anti-proliferative agent for the prevention of coronary restenosis.
xref: CHEMBL219410
synonym: ABT 578
synonym: ABT-578
synonym: ABT578
approved: f
ligand name: zotarolimus
type: SyntheticOrganicLigand

XL388
in ch i key: LNFBAYSBVQBKFR-UHFFFAOYSA-N
in ch i: InChI=1S/C23H22FN3O4S/c1-14-18(5-7-20(22(14)24)32(2,29)30)23(28)27-9-10-31-19-6-3-15(11-17(19)13-27)16-4-8-21(25)26-12-16/h3-8,11-12H,9-10,13H2,1-2H3,(H2,25,26)
comment: XL388 is a highly potent, selective, ATP-competitive inhibitor of mTOR. Its discovery is described in <Reference id=26344/>, where it is compound 28.
iupac name: [7-(6-aminopyridin-3-yl)-3,5-dihydro-2H-1,4-benzoxazepin-4-yl]-(3-fluoro-2-methyl-4-methylsulfonylphenyl)methanone
xref: CHEMBL2333365
synonym: XL-388
approved: f
ligand name: XL388
type: SyntheticOrganicLigand

XL019
in ch i key: ISOCDPQFIXDIMS-QHCPKHFHSA-N
in ch i: InChI=1S/C25H28N6O2/c32-24(23-2-1-12-26-23)28-19-5-3-18(4-6-19)22-11-13-27-25(30-22)29-20-7-9-21(10-8-20)31-14-16-33-17-15-31/h3-11,13,23,26H,1-2,12,14-17H2,(H,28,32)(H,27,29,30)/t23-/m0/s1
comment: XL019 is a selective inhibitor of Janus kinase 2 (JAK2) <Reference id=26341/>.
iupac name: (2S)-N-[4-[2-(4-morpholin-4-ylanilino)pyrimidin-4-yl]phenyl]pyrrolidine-2-carboxamide
synonym: XL 019
synonym: XL-019
approved: f
ligand name: XL019
type: SyntheticOrganicLigand

AKN-028
canonical SMILES: Nc1ncc(nc1Nc1ccc2c(c1)cc[nH]2)c1ccncc1
isomeric SMILES: Nc1ncc(nc1Nc1ccc2c(c1)cc[nH]2)c1ccncc1
in ch i key: JLRIJKVMMZEKDF-UHFFFAOYSA-N
in ch i: InChI=1S/C17H14N6/c18-16-17(22-13-1-2-14-12(9-13)5-8-20-14)23-15(10-21-16)11-3-6-19-7-4-11/h1-10,20H,(H2,18,21)(H,22,23)
comment: AKN-028 is an orally bioavailable protein tyrosine kinase inhibitor for FMS-related tyrosine kinase 3 (FLT3) and stem cell factor receptor (SCFR; KIT), that was developed for potential antineoplastic activity <Reference id=26335/><Reference id=26336/>. The compound inhibits wild-type and mutant FLT3 and KIT kinases.
iupac name: 3-N-(1H-indol-5-yl)-5-pyridin-4-ylpyrazine-2,3-diamine
synonym: AKN028
synonym: AKN 028
approved: f
ligand name: AKN-028
type: SyntheticOrganicLigand

BMS-908662
in ch i key: MMNNTJYFHUDSKL-UHFFFAOYSA-N
in ch i: InChI=1S/C24H19ClN4O4/c1-13-7-9-15(25)12-20(13)29-21(30)16-5-3-4-6-17(16)24(29,32)14-8-10-18-19(11-14)27-22(26-18)28-23(31)33-2/h3-12,32H,1-2H3,(H2,26,27,28,31)
comment: BMS908662 is an orally active, small molecule B-RAF inhibitor with potential antineoplastic activity.
iupac name: methyl N-[6-[2-(5-chloro-2-methylphenyl)-1-hydroxy-3-oxoisoindol-1-yl]-1H-benzimidazol-2-yl]carbamate
synonym: XL281
synonym: BMS 908662
synonym: BMS908662
approved: f
ligand name: BMS-908662
type: SyntheticOrganicLigand

GSK2636771
in ch i key: XTKLTGBKIDQGQL-UHFFFAOYSA-N
in ch i: InChI=1S/C22H22F3N3O3/c1-13-15(4-3-5-18(13)22(23,24)25)12-28-14(2)26-20-17(21(29)30)10-16(11-19(20)28)27-6-8-31-9-7-27/h3-5,10-11H,6-9,12H2,1-2H3,(H,29,30)
comment: GSK2636771 is a potent, orally bioavailable, PI3Kβ-selective inhibitor, with anticancer effects in PTEN null cells <Reference id=26334/>.
iupac name: 2-methyl-1-[[2-methyl-3-(trifluoromethyl)phenyl]methyl]-6-morpholin-4-ylbenzimidazole-4-carboxylic acid
xref: CHEMBL3188551
synonym: GSK-2636771
approved: f
ligand name: GSK2636771
type: SyntheticOrganicLigand

rociletinib
in ch i key: HUFOZJXAKZVRNJ-UHFFFAOYSA-N
in ch i: InChI=1S/C27H28F3N7O3/c1-4-24(39)32-18-6-5-7-19(14-18)33-25-21(27(28,29)30)16-31-26(35-25)34-22-9-8-20(15-23(22)40-3)37-12-10-36(11-13-37)17(2)38/h4-9,14-16H,1,10-13H2,2-3H3,(H,32,39)(H2,31,33,34,35)
comment: Rociletinib is an orally bioavailable small molecule, irreversible inhibitor of epidermal growth factor receptor (EGFR) with potential antineoplastic activity <Reference id=26331/>. This compound was designed to selectively target both the initial activating EGFR mutations and the T790M resistance mutation which confers acquired tumour resistance to first-generation inhibitors such as <Ligand id=4920/> and <Ligand id=4941/>. Third-generation mutant EGFR inhibitors like rociletinib are being developed to circumvent dose-limiting WT EGFR-driven toxicities such as gastrointestinal toxicity and rash. The progress being made in developing advanced generation EGFR inhibitors is discussed by Yu and Riely (2013) <Reference id=26332/> and Ou and Soo (2015) <Reference id=31220/>.
iupac name: N-[3-[[2-[4-(4-acetylpiperazin-1-yl)-2-methoxyanilino]-5-(trifluoromethyl)pyrimidin-4-yl]amino]phenyl]prop-2-enamide
synonym: CO-1686
synonym: AVL-301
approved: f
ligand name: rociletinib
type: SyntheticOrganicLigand

L-asparagine
canonical SMILES: NC(=O)CC(C(=O)O)N
isomeric SMILES: NC(=O)C[C@@H](C(=O)O)N
in ch i key: DCXYFEDJOCDNAF-REOHCLBHSA-N
in ch i: InChI=1S/C4H8N2O3/c5-2(4(8)9)1-3(6)7/h2H,1,5H2,(H2,6,7)(H,8,9)/t2-/m0/s1
iupac name: (2S)-2-amino-3-carbamoylpropanoic acid
xref: CHEMBL58832
synonym: Agedoite
synonym: Altheine
synonym: Crystal VI
approved: f
ligand name: L-asparagine
type: MetaboliteLigand

ZSTK474
in ch i key: HGVNLRPZOWWDKD-UHFFFAOYSA-N
in ch i: InChI=1S/C19H21F2N7O2/c20-15(21)16-22-13-3-1-2-4-14(13)28(16)19-24-17(26-5-9-29-10-6-26)23-18(25-19)27-7-11-30-12-8-27/h1-4,15H,5-12H2
comment: ZSTK474 is a novel orally bioavailable inhibitor of phosphoinositide 3-kinase (PI3K) that strongly inhibits cancer cell proliferation <Reference id=26329/><Reference id=26330/>.
iupac name: 2-(difluoromethyl)-1-[4,6-di(morpholin-4-yl)-1,3,5-triazin-2-yl]benzimidazole
xref: CHEMBL586702
synonym: TCMDC-137004
synonym: ZSTK-474
synonym: ZSTK 474
approved: f
ligand name: ZSTK474
type: SyntheticOrganicLigand

voxtalisib
in ch i key: HJSSPYJVWLTYHG-UHFFFAOYSA-N
in ch i: InChI=1S/C31H29N5O6S/c1-19-9-10-20(15-28(19)42-4)31(37)33-21-11-13-25(14-12-21)43(38,39)36-30-29(34-26-7-5-6-8-27(26)35-30)32-22-16-23(40-2)18-24(17-22)41-3/h5-18H,1-4H3,(H,32,34)(H,33,37)(H,35,36)
comment: Voxtalisib is an orally bioavailable small molecule inhibitor of phosphatidylinositol 3 kinase (PI3K) and mammalian target of rapamycin (mTOR) kinases in the PI3K/mTOR signaling pathway, with potential antineoplastic activity <Reference id=26328/>.
iupac name: N-[4-[[3-(3,5-dimethoxyanilino)quinoxalin-2-yl]sulfamoyl]phenyl]-3-methoxy-4-methylbenzamide
synonym: XL765
synonym: SAR-245409
synonym: SAR245409
approved: f
ligand name: voxtalisib
type: SyntheticOrganicLigand

pilaralisib
in ch i key: MQMKRQLTIWPEDM-UHFFFAOYSA-N
in ch i: InChI=1S/C21H16N6O2S2/c1-13-6-9-15(10-7-13)31(28,29)27-21-20(23-16-4-2-3-5-17(16)24-21)22-14-8-11-18-19(12-14)26-30-25-18/h2-12H,1H3,(H,22,23)(H,24,27)
comment: Pilaralisib is an orally bioavailable small molecule inhibitor of the class I phosphatidylinositol 3 kinase (PI3K) family of lipid kinases, with potential antineoplastic activity <Reference id=26327/><Reference id=26326/>.
iupac name: N-[3-(2,1,3-benzothiadiazol-6-ylamino)quinoxalin-2-yl]-4-methylbenzenesulfonamide
xref: CHEMBL3218575
synonym: XL147
synonym: SAR-245408
synonym: XL 147
synonym: XL-147
approved: f
ligand name: pilaralisib
type: SyntheticOrganicLigand

MK-2461
in ch i key: JGEBLDKNWBUGRZ-HXUWFJFHSA-N
in ch i: InChI=1S/C24H25N5O5S/c1-28-13-18(12-26-28)17-9-22-23(25-11-17)6-4-16-3-5-19(10-21(16)24(22)30)27-35(31,32)29(2)14-20-15-33-7-8-34-20/h3-6,9-13,20,27H,7-8,14-15H2,1-2H3/t20-/m1/s1
comment: MK-2461 is a novel ATP-competitive inhibitor of mutant activated c-Met and also exhibits significant inhibitory activities against fibroblast growth factor receptor (FGFR), platelet-derived growth factor receptor, and other receptor tyrosine kinases <Reference id=26325/>.
iupac name: 9-[[[(2R)-1,4-dioxan-2-yl]methyl-methylsulfamoyl]amino]-2-(1-methylpyrazol-4-yl)-11-oxobenzo[1,2]cyclohepta[2,4-b]pyridine
xref: CHEMBL1822792
synonym: MK 2461
approved: f
ligand name: MK-2461
type: SyntheticOrganicLigand

ME-344
in ch i key: QVCAATSEPLQVBX-FPOVZHCZSA-N
in ch i: InChI=1S/C22H20O4/c1-13-20(25)11-10-18-21(15-4-8-17(24)9-5-15)19(12-26-22(13)18)14-2-6-16(23)7-3-14/h2-11,19,21,23-25H,12H2,1H3/t19-,21-/m0/s1
comment: ME-344 is an active metabolite of NV-128 <Reference id=26323/>, a novel flavonoid small molecule inhibitor of the mammalian target of rapamycin (mTOR).
iupac name: (3R,4S)-3,4-bis(4-hydroxyphenyl)-8-methyl-3,4-dihydro-2H-chromen-7-ol
approved: f
ligand name: ME-344
type: SyntheticOrganicLigand

rabusertib
in ch i key: SYYBDNPGDKKJDU-ZDUSSCGKSA-N
in ch i: InChI=1S/C18H22BrN5O3/c1-11-5-16(27-10-13-8-20-3-4-26-13)15(6-14(11)19)23-18(25)24-17-9-21-12(2)7-22-17/h5-7,9,13,20H,3-4,8,10H2,1-2H3,(H2,22,23,24,25)/t13-/m0/s1
comment: Rabusertib is an inhibitor of the cell cycle checkpoint kinase 1 (CHK1) with potential chemopotentiating activity <Reference id=26320/><Reference id=26321/><Reference id=26322/>. It is the first selective CHK1 inhibitor to enter clinical cancer trials
iupac name: N-(5-bromo-4-methyl-2-{[(2S)-morpholin-2-yl]methoxy}phenyl)-N'-(5-methylpyrazin-2-yl)urea
xref: CHEMBL3039517
synonym: LY2603618
synonym: LY-2603618
approved: f
ligand name: rabusertib
type: SyntheticOrganicLigand

ralimetinib
in ch i key: XPPBBJCBDOEXDN-UHFFFAOYSA-N
in ch i: InChI=1S/C24H29FN6/c1-23(2,3)13-31-20-17(28-22(31)26)12-11-16(27-20)19-18(14-7-9-15(25)10-8-14)29-21(30-19)24(4,5)6/h7-12H,13H2,1-6H3,(H2,26,28)(H,29,30)
comment: Ralimetinib is a potent and selective, ATP-competitive inhibitor of p38 MAPK α and β (MAPK14 and MAPK11 respectively) <Reference id=26318/><Reference id=38275/>. The compound is delivered orally as the dimesylate salt (PubChem CID 11570805). It is compound 40 in Mader et al. (2008) <Reference id=26319/>. SARS-CoV-2: p38 MAPK activity has been reported to be upregulated following SARS-CoV-2 infection of host cells in vitro. Ralimetinib produces an antiviral effect with an IC50 of 873 nM <Reference id=39830/>.
iupac name: 5-[2-tert-butyl-5-(4-fluorophenyl)-3H-imidazol-4-yl]-3-(2,2-dimethylpropyl)imidazo[5,4-b]pyridin-2-amine
xref: CHEMBL2364626
synonym: LY2228820
synonym: LY-2228820
synonym: LY-2228820 free base
approved: f
ligand name: ralimetinib
type: SyntheticOrganicLigand

LY2090314
in ch i key: HRJWTAWVFDCTGO-UHFFFAOYSA-N
in ch i: InChI=1S/C28H25FN6O3/c29-18-12-17-15-34(28(38)32-7-3-1-4-8-32)11-10-33-16-20(19(13-18)25(17)33)23-24(27(37)31-26(23)36)21-14-30-22-6-2-5-9-35(21)22/h2,5-6,9,12-14,16H,1,3-4,7-8,10-11,15H2,(H,31,36,37)
comment: LY2090314 is a potent inhibitor of glycogen synthase kinase-3 (GSK3) <Reference id=26314/><Reference id=26315/>. The discovery of LY2090314 is described by Engler et al. (2004) <Reference id=26314/> where it is compound 12.
xref: CHEMBL362558
synonym: LY-2090314
approved: f
ligand name: LY2090314
type: SyntheticOrganicLigand

tirbanibulin
in ch i key: HUNGUWOZPQBXGX-UHFFFAOYSA-N
in ch i: InChI=1S/C26H29N3O3/c30-26(28-19-21-4-2-1-3-5-21)18-24-9-6-23(20-27-24)22-7-10-25(11-8-22)32-17-14-29-12-15-31-16-13-29/h1-11,20H,12-19H2,(H,28,30)
comment: Tirbanibulin (KX2-391) is an orally bioavailable small molecule with a dual mode of action. It is a Src kinase inhibitor with potential antiproliferative activity <Reference id=26308/><Reference id=35304/> and an inhibitor of tubulin polymerization <Reference id=35304/>. Synthesis of KX2-391 is described in US patent US20060160800 <Reference id=26313/>, where it is compound 134.
iupac name: 2-[5-[4-(2-morpholin-4-ylethoxy)phenyl]pyridin-2-yl]-N-(phenylmethyl)acetamide
xref: CHEMBL571546
synonym: KX 2-391
synonym: KX-2-391
synonym: KX-01
synonym: KX2-391
synonym: Klisyri®
approved: t
ligand name: tirbanibulin
type: SyntheticOrganicLigand

golvatinib
in ch i key: UQRCJCNVNUFYDX-UHFFFAOYSA-N
in ch i: InChI=1S/C33H37F2N7O4/c1-40-16-18-41(19-17-40)24-9-14-42(15-10-24)32(45)39-29-21-26(8-13-36-29)46-25-6-7-28(27(35)20-25)38-31(44)33(11-12-33)30(43)37-23-4-2-22(34)3-5-23/h2-8,13,20-21,24H,9-12,14-19H2,1H3,(H,37,43)(H,38,44)(H,36,39,45)
comment: Golvatinib is an orally bioavailable dual kinase inhibitor of c-Met (hepatocyte growth factor receptor) and VEGFR2 (vascular endothelial growth factor receptor-2) tyrosine kinases with potential antineoplastic activity <Reference id=26307/>. It is the first kinase inhibitor with this dual action.
iupac name: N'-[2-fluoro-4-[2-[[4-(4-methylpiperazin-1-yl)piperidine-1-carbonyl]amino]pyridin-4-yl]oxyphenyl]-N-(4-fluorophenyl)cyclopropane-1,1-dicarboxamide
xref: CHEMBL3039525
synonym: E7050
synonym: E-7050
approved: f
ligand name: golvatinib
type: SyntheticOrganicLigand

alpelisib
in ch i key: STUWGJZDJHPWGZ-LBPRGKRZSA-N
comment: Alpelisib is an orally bioavailable phosphatidylinositol 3-kinase (PI3K) inhibitor that exhibits antineoplastic activity. It is selective for the α isoform (PIK3CA). It was the first PIK3CA inhibitor to be approved for the treatment of breast cancer.
iupac name: (2S)-1-N-[4-methyl-5-[2-(1,1,1-trifluoro-2-methylpropan-2-yl)pyridin-4-yl]-1,3-thiazol-2-yl]pyrrolidine-1,2-dicarboxamide
xref: CHEMBL2396661
synonym: BYL719
synonym: BYL-719
synonym: BYL 719
synonym: NVP-BYL719
synonym: Piqray®
synonym: Vijoice®
approved: t
ligand name: alpelisib
type: SyntheticOrganicLigand

BMS-911543
in ch i key: JCINBYQJBYJGDM-UHFFFAOYSA-N
in ch i: InChI=1S/C23H28N8O/c1-5-30-17(23(32)31(14-6-7-14)15-8-9-15)11-16-20-19(24-12-28(20)3)21(26-22(16)30)25-18-10-13(2)29(4)27-18/h10-12,14-15H,5-9H2,1-4H3,(H,25,26,27)
comment: BMS-911543 is an orally available ATP-competitive inhibitor of Janus kinase 2 (JAK2) with potential antineoplastic activity. Its discovery is described by Purandare et al. (2012) <Reference id=26304/>.
synonym: BMS 911543
synonym: BMS911543
approved: f
ligand name: BMS-911543
type: SyntheticOrganicLigand

BMS-777607
in ch i key: VNBRGSXVFBYQNN-UHFFFAOYSA-N
comment: BMS-777607is a selective and orally bioavailable MET tyrosine kinase (hepatocyte growth factor receptor) inhibitor with potential antineoplastic activity. Its discovery is described by Schroeder et al. (2009) <Reference id=26303/> where it is compound 10. It also has significant activity against other receptor tyrosine kinases, with details presented in the Biological activity tab..
iupac name: N-[4-(2-amino-3-chloropyridin-4-yl)oxy-3-fluorophenyl]-4-ethoxy-1-(4-fluorophenyl)-2-oxopyridine-3-carboxamide
xref: CHEMBL460702
synonym: BMS 777607
synonym: BMS777607
approved: f
ligand name: BMS-777607
type: SyntheticOrganicLigand

BMS-754807
in ch i key: LQVXSNNAFNGRAH-QHCPKHFHSA-N
in ch i: InChI=1S/C23H24FN9O/c1-23(21(34)26-15-7-8-18(24)25-13-15)9-3-10-32(23)22-28-20(17-4-2-11-33(17)31-22)27-19-12-16(29-30-19)14-5-6-14/h2,4,7-8,11-14H,3,5-6,9-10H2,1H3,(H,26,34)(H2,27,28,29,30,31)/t23-/m0/s1
comment: BMS-754807 is an orally bioavailable antagonist of human insulin-like growth factor type I receptor (IGF-1R) with potential antineoplastic activity. Its discovery is described in Wittman et al. (2009) <Reference id=26302/>, where it is compound 9d.
iupac name: (2S)-1-[4-[(5-cyclopropyl-1H-pyrazol-3-yl)amino]pyrrolo[2,1-f][1,2,4]triazin-2-yl]-N-(6-fluoropyridin-3-yl)-2-methylpyrrolidine-2-carboxamide
xref: CHEMBL575448
synonym: BMS 754807
synonym: BMS754807
approved: f
ligand name: BMS-754807
type: SyntheticOrganicLigand

BGT-226
in ch i key: BMMXYEBLEBULND-UHFFFAOYSA-N
in ch i: InChI=1S/C28H25F3N6O2/c1-35-24-16-33-22-6-3-17(18-4-8-25(39-2)34-15-18)13-20(22)26(24)37(27(35)38)19-5-7-23(21(14-19)28(29,30)31)36-11-9-32-10-12-36/h3-8,13-16,32H,9-12H2,1-2H3
comment: BGT-226 is a novel pan class I PI3K and mTOR inhibitor <Reference id=26301/>. The oral formulation of BGT-226 contains its maleate salt (PubChem CID 57336745).
iupac name: 8-(6-methoxypyridin-3-yl)-3-methyl-1-[4-piperazin-1-yl-3-(trifluoromethyl)phenyl]imidazo[5,4-c]quinolin-2-one
xref: CHEMBL3218578
synonym: BGT226
synonym: NPV-BGT226
synonym: BGT-226 free base
synonym: BGT 226
approved: f
ligand name: BGT-226
type: SyntheticOrganicLigand

dactolisib
in ch i key: JOGKUKXHTYWRGZ-UHFFFAOYSA-N
in ch i: InChI=1S/C30H23N5O/c1-30(2,18-31)22-9-11-23(12-10-22)35-28-24-15-19(21-14-20-6-4-5-7-25(20)32-16-21)8-13-26(24)33-17-27(28)34(3)29(35)36/h4-17H,1-3H3
comment: Dactolisib is an orally bioavailable dual PI3K/mTOR inhibitor with potential antineoplastic activity. It inhibits all of the PI3K isoforms <Reference id=26299/> and in addition, it effectively targets ATR with IC50 of 21 nM in cells <Reference id=37570/>. COVID-19: Dactolisib (as RTB101) is being evaluated as post-exposure prophylaxis for SARS-CoV-2 infection.
iupac name: 2-methyl-2-[4-(3-methyl-2-oxo-8-quinolin-3-ylimidazo[4,5-c]quinolin-1-yl)phenyl]propanenitrile
xref: CHEMBL1879463
synonym: NVP-BEZ235
synonym: BEZ235
synonym: BEZ 235
synonym: BEZ-235
synonym: NVP-BEZ 235
synonym: RTB101
synonym: RTB-101
approved: f
ligand name: dactolisib
type: SyntheticOrganicLigand

AT-9283
isomeric SMILES: O=C(Nc1c[nH][nH]/c/1=C/1/N=c2c(=N1)ccc(c2)CN1CCOCC1)NC1CC1
in ch i key: VRXXZJLHPWWXIX-ZCXUNETKSA-N
in ch i: InChI=1S/C19H23N7O2/c27-19(21-13-2-3-13)24-16-10-20-25-17(16)18-22-14-4-1-12(9-15(14)23-18)11-26-5-7-28-8-6-26/h1,4,9-10,13,20,25H,2-3,5-8,11H2,(H2,21,24,27)/b18-17-
comment: AT-9283 is a potent Janus kinase 2 and 3 (JAK2/3) and Aurora kinase inhibitor <Reference id=26297/>. It is compound 16 in Howard et al. (2009) <Reference id=26297/>, PubChem CID 11496629 shows the tautomer as drawn in <Reference id=26297/>. CHEMBL495727 also represents a tautomeric alternative structure for AT-9283.
iupac name: 1-cyclopropyl-3-[(3Z)-3-[5-(morpholin-4-ylmethyl)benzimidazol-2-ylidene]-1,2-dihydropyrazol-4-yl]urea
synonym: AT9283
synonym: AT 9283
approved: f
ligand name: AT-9283
type: SyntheticOrganicLigand

tivantinib
in ch i key: UCEQXRCJXIVODC-PMACEKPBSA-N
in ch i: InChI=1S/C23H19N3O2/c27-22-19(16-11-24-18-9-2-1-7-14(16)18)20(23(28)25-22)17-12-26-10-4-6-13-5-3-8-15(17)21(13)26/h1-3,5,7-9,11-12,19-20,24H,4,6,10H2,(H,25,27,28)/t19-,20-/m0/s1
comment: Tivantinib is an allosteric inhibitor of c-MET kinase (hepatocyte growth factor receptor), with antineoplastic potential <Reference id=26293/>.
xref: CHEMBL2103882
synonym: ARQ-197
synonym: Arqule
synonym: ARQ 197
synonym: ARQ197
approved: f
ligand name: tivantinib
type: SyntheticOrganicLigand

volasertib
in ch i key: SXNJFOWDRLKDSF-STROYTFGSA-N
in ch i: InChI=1S/C34H50N8O3/c1-6-28-33(44)39(4)29-20-35-34(38-31(29)42(28)22(2)3)37-27-14-9-24(19-30(27)45-5)32(43)36-25-10-12-26(13-11-25)41-17-15-40(16-18-41)21-23-7-8-23/h9,14,19-20,22-23,25-26,28H,6-8,10-13,15-18,21H2,1-5H3,(H,36,43)(H,35,37,38)/t25-,26-,28-/m1/s1
comment: Volasertib is an ATP-competitive, investigational inhibitor of polo-like kinase 1 (PLK1). It is the second in a novel class of drugs called dihydropteridinone derivatives <Reference id=26287/>. This compound is represented on PubChem by CID 10461508. This CID varies slightly in its chiral specification from our ligand entry. Our structure was drawn from the image submitted to the WHO for the INN (note that the long chemical name provided for the INN registration is not sufficient to resolve absolute stereochemistry as depicted in the accompanying image). Some bioactivity may be linked to the trihydrochloride salt form.
xref: CHEMBL1233528
synonym: BI-6727
synonym: BI 6727
synonym: BI6727
approved: f
ligand name: volasertib
type: SyntheticOrganicLigand

cyclopenthiazide
in ch i key: BKYKPTRYDKTTJY-UHFFFAOYSA-N
comment: The drug used as cyclopenthiazide is a racemic mixture of (R)- and (S)-stereoisomers (PubChem CIDs 6604279 and 40463616 respectively).
iupac name: 6-chloro-3-(cyclopentylmethyl)-1,1-dioxo-3,4-dihydro-2H-benzo[e][1,2,4]thiadiazine-7-sulfonamide
xref: CHEMBL1373254
synonym: SU-8341
synonym: cyclomethiazide
approved: t
ligand name: cyclopenthiazide
type: SyntheticOrganicLigand

sotrastaurin
in ch i key: OAVGBZOFDPFGPJ-UHFFFAOYSA-N
in ch i: InChI=1S/C25H22N6O2/c1-30-10-12-31(13-11-30)25-27-19-9-5-3-7-16(19)22(28-25)21-20(23(32)29-24(21)33)17-14-26-18-8-4-2-6-15(17)18/h2-9,14,26H,10-13H2,1H3,(H,29,32,33)
comment: The discovery of sotrastaurin is described in <Reference id=26286/>. The compound is a a potent and selective pan-PKC inhibitor.
iupac name: 3-(1H-indol-3-yl)-4-[2-(4-methylpiperazin-1-yl)quinazolin-4-yl]pyrrole-2,5-dione
xref: CHEMBL565612
synonym: AEB071
synonym: AEB 071
synonym: AEB-071
approved: f
ligand name: sotrastaurin
type: SyntheticOrganicLigand

MK-2206
in ch i key: ULDXWLCXEDXJGE-UHFFFAOYSA-N
in ch i: InChI=1S/C25H21N5O/c26-25(12-4-13-25)18-9-7-17(8-10-18)22-19(16-5-2-1-3-6-16)15-20-21(27-22)11-14-30-23(20)28-29-24(30)31/h1-3,5-11,14-15H,4,12-13,26H2,(H,29,31)
comment: MK-2206 is an orally bioavailable allosteric inhibitor of the serine/threonine protein kinase Akt (protein kinase B) with potential antineoplastic activity <Reference id=26277/><Reference id=26278/><Reference id=26279/>.
iupac name: 8-[4-(1-aminocyclobutyl)phenyl]-9-phenyl-2H-[1,2,4]triazolo[3,4-f][1,6]naphthyridin-3-one
xref: CHEMBL1079175
synonym: MK 2206
synonym: MK2206
approved: f
ligand name: MK-2206
type: SyntheticOrganicLigand

tesevatinib
in ch i key: HVXKQKFEHMGHSL-GOOCMWNKSA-N
comment: Tesevatinib (XL-647) is an orally bioavailable small-molecule receptor tyrosine kinase (RTK) inhibitor with broad spectrum activity againt EGFRs and VEGFRs <Reference id=26275/>, and which has pre-clinical antineoplastic potential <Reference id=26274/>. The two CAS numbers associated with this compound (781613-23-8 and 651031-01-5) indicate a third chiral centre, however the structure shown here does not specify stereochemistry at this point.
iupac name: 7-[[(3aR,6aS)-2-methyl-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrol-5-yl]methoxy]-N-(3,4-dichloro-2-fluorophenyl)-6-methoxyquinazolin-4-amine
synonym: EXEL-7647
synonym: XL647
synonym: KD-019
synonym: XL-647
approved: f
ligand name: tesevatinib
type: SyntheticOrganicLigand

MK-8776
canonical SMILES: Cn1ncc(c1)c1cnn2c1nc(C1CCCNC1)c(c2N)Br
isomeric SMILES: Cn1ncc(c1)c1cnn2c1nc(C1CCCNC1)c(c2N)Br
in ch i key: GMIZZEXBPRLVIV-UHFFFAOYSA-N
in ch i: InChI=1S/C15H18BrN7/c1-22-8-10(6-19-22)11-7-20-23-14(17)12(16)13(21-15(11)23)9-3-2-4-18-5-9/h6-9,18H,2-5,17H2,1H3
comment: The discovery and synthesis of MK-8776 (a.k.a. SCH 900776) is described in <Reference id=26270/>, where it is compound 9b. In the article by Guzi et al (2011) <Reference id=26271/>, the compound is shown with an (R) stereo center (see PubChem CID 46239015), whereas it is shown with no stereochemistry by Labroli et al (2011). MK-8776 is primarily an inhibitor of checkpoint kinase 1 (CHK1), with minimal inhibitory activity on cyclin dependent kinase 2 (CDK2).
iupac name: 6-bromo-3-(1-methylpyrazol-4-yl)-5-piperidin-3-ylpyrazolo[5,1-b]pyrimidin-7-amine
xref: CHEMBL1643208
synonym: MK 8776
synonym: SCH 900776
synonym: SCH900776
approved: f
ligand name: MK-8776
type: SyntheticOrganicLigand

refametinib
in ch i key: RDSACQWTXKSHJT-NSHDSACASA-N
comment: Refametinib (BAY-869766) is a potent and selective, allosteric inhibitor of MEK1/2 with potential antineoplastic activity <Reference id=26268/>. This compound is available via AstraZeneca's openinnovation toolbox resource, which indicates that refametinib is associated with a risk of fetal toxicity.
iupac name: N-[3,4-difluoro-2-(2-fluoro-4-iodoanilino)-6-methoxyphenyl]-1-[(2S)-2,3-dihydroxypropyl]cyclopropane-1-sulfonamide
synonym: RDEA119
synonym: RDEA-119
synonym: BAY-869766
synonym: BAY 869766
approved: f
ligand name: refametinib
type: SyntheticOrganicLigand

sonolisib
in ch i key: QIUASFSNWYMDFS-NILGECQDSA-N
in ch i: InChI=1S/C29H35NO8/c1-7-11-30(12-8-2)14-17-23-26(34)25(33)22-18-9-10-20(32)28(18,4)13-19(37-16(3)31)24(22)29(23,5)21(15-36-6)38-27(17)35/h7-8,14,18-19,21,34H,1-2,9-13,15H2,3-6H3/b17-14+/t18-,19+,21+,28-,29-/m0/s1
comment: Sonolisib is a small-molecule <Ligand id=6060/> inhibitor of the alpha, gamma, and delta isoforms of phosphoinositide 3-kinase (PI3K) with potential antineoplastic activity <Reference id=26263/>. It is compound 4 in Zask et al. (2008) <Reference id=26265/>.
iupac name: [(3aR,6E,9S,9aR,10R,11aS)-6-[(di(prop-2-enyl)amino)methylidene]-5-hydroxy-9-(methoxymethyl)-9a,11a-dimethyl-1,4,7-trioxo-2,3,3a,9,10,11-hexahydroindeno[7,6-h]isochromen-10-yl] acetate
xref: CHEMBL411907
synonym: PX-866
synonym: PX866
approved: f
ligand name: sonolisib
type: SyntheticOrganicLigand

gedatolisib
in ch i key: DWZAEMINVBZMHQ-UHFFFAOYSA-N
in ch i: InChI=1S/C32H41N9O4/c1-38(2)27-11-13-39(14-12-27)29(42)24-5-9-26(10-6-24)34-32(43)33-25-7-3-23(4-8-25)28-35-30(40-15-19-44-20-16-40)37-31(36-28)41-17-21-45-22-18-41/h3-10,27H,11-22H2,1-2H3,(H2,33,34,43)
comment: Gedatolisib is an orally bioavailable small molecule inhibitor of phosphatidylinositol 3 kinase (PI3K) and mammalian target of rapamycin (mTOR) with potential antineoplastic activity <Reference id=26260/><Reference id=26261/><Reference id=26262/>.
iupac name: 1-[4-[4-(dimethylamino)piperidine-1-carbonyl]phenyl]-3-[4-(4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl)phenyl]urea
xref: CHEMBL592445
synonym: PKI 587
synonym: PF-05212384
synonym: PKI-587
approved: f
ligand name: gedatolisib
type: SyntheticOrganicLigand

GSK2256098
in ch i key: BVAHPPKGOOJSPU-UHFFFAOYSA-N
in ch i: InChI=1S/C20H23ClN6O2/c1-12(2)27-19(9-13(3)25-27)24-18-10-17(15(21)11-22-18)23-16-8-6-5-7-14(16)20(28)26-29-4/h5-12H,1-4H3,(H,26,28)(H2,22,23,24)
comment: GSK2256098 is a small molecule focal adhesion kinase (FAK) inhibitor with potential antiangiogenic and antineoplastic activity <Reference id=26258/><Reference id=26179/><Reference id=26183/>.
iupac name: 2-[(5-chloro-2-{[3-methyl-1-(propan-2-yl)-1H-pyrazol-5-yl]amino}pyridin-4-yl)amino]-N-methoxybenzamide
synonym: GSK-2256098
synonym: GSK 2256098
approved: f
ligand name: GSK2256098
type: SyntheticOrganicLigand

[14C]ascorbic acid
canonical SMILES: OCC(C1OC(=O)C(=C1O)O)O
isomeric SMILES: OC[C@@H]([C@H]1OC(=O)C(=C1O)O)O
in ch i key: CIWBSHSKHKDKBQ-JLAZNSOCSA-N
in ch i: InChI=1S/C6H8O6/c7-1-2(8)5-3(9)4(10)6(11)12-5/h2,5,7-10H,1H2/t2-,5+/m0/s1
iupac name: (5R)-5-[(1S)-1,2-dihydroxyethyl]-3,4-dihydroxy-2,5-dihydrofuran-2-one
xref: CHEMBL196
synonym: [14C]-ascorbic acid
approved: f
ligand name: [14C]ascorbic acid
type: SyntheticOrganicLigand

milciclib
in ch i key: RXZMYLDMFYNEIM-UHFFFAOYSA-N
in ch i: InChI=1S/C25H32N8O/c1-25(2)14-16-15-27-24(29-20(16)22-19(25)21(23(34)26-3)30-32(22)5)28-17-6-8-18(9-7-17)33-12-10-31(4)11-13-33/h6-9,15H,10-14H2,1-5H3,(H,26,34)(H,27,28,29)
comment: Milciclib is an orally bioavailable inhibitor of cyclin-dependent kinases (CDKs) and neurotrophic tyrosine kinase, receptor, type 1 (aka TRKA) <Reference id=26256/>. It is compound 28 in Brasca et al (2009) <Reference id=26256/>. Milciclib exhibits a notable level of promiscuity across the CDKs <Reference id=36225/>.
iupac name: N,1,4,4-tetramethyl-8-[[4-(4-methylpiperazin-1-yl)phenyl]amino]-5H-pyrazolo[4,5-h]quinazoline-3-carboxamide
xref: CHEMBL564829
synonym: PHA-848125
synonym: PHA848125
synonym: PHA 848125
approved: f
ligand name: milciclib
type: SyntheticOrganicLigand

danusertib
in ch i key: XKFTZKGMDDZMJI-HSZRJFAPSA-N
in ch i: InChI=1S/C26H30N6O3/c1-30-12-14-31(15-13-30)20-10-8-19(9-11-20)25(33)27-24-21-16-32(17-22(21)28-29-24)26(34)23(35-2)18-6-4-3-5-7-18/h3-11,23H,12-17H2,1-2H3,(H2,27,28,29,33)/t23-/m1/s1
comment: Danusertib is a small-molecule Aurora kinase inhibitor with potential antineoplastic activity. Its discovery is reported in <Reference id=26255/> where it is compound 9d.
iupac name: N-[5-[(2R)-2-methoxy-2-phenylacetyl]-4,6-dihydro-1H-pyrrolo[3,4-d]pyrazol-3-yl]-4-(4-methylpiperazin-1-yl)benzamide
xref: CHEMBL402548
synonym: PHA-739358
synonym: PHA 739358
approved: f
ligand name: danusertib
type: SyntheticOrganicLigand

PF-04691502
in ch i key: XDLYKKIQACFMJG-WKILWMFISA-N
in ch i: InChI=1S/C22H27N5O4/c1-13-17-11-18(14-3-8-19(30-2)24-12-14)21(29)27(20(17)26-22(23)25-13)15-4-6-16(7-5-15)31-10-9-28/h3,8,11-12,15-16,28H,4-7,9-10H2,1-2H3,(H2,23,25,26)/t15-,16-
comment: PF-04691502 is an ATP-competitive dual PI3K/mTOR inhibitor. The discovery and structure of PF-04691502 is reported in <Reference id=26253/>. PubChem CID 25033539 shows the chemical structure without stereochemistry.
iupac name: 2-amino-8-[trans-4-(2-hydroxyethoxy)cyclohexyl]-6-(6-methoxypyridin-3-yl)-4-methylpyrido[2,3-d]pyrimidin-7(8H)-one
xref: CHEMBL1234354
synonym: PF 04691502
synonym: PF04691502
approved: f
ligand name: PF-04691502
type: SyntheticOrganicLigand

mirdametinib
in ch i key: SUDAHWBOROXANE-SECBINFHSA-N
comment: Mirdametinib (PD 0325901) is a selective and non ATP-competitive MEK inhibitor <Reference id=26251/>.
iupac name: N-[(2R)-2,3-dihydroxypropoxy]-3,4-difluoro-2-[(2-fluoro-4-iodophenyl)amino]benzamide
xref: CHEMBL507361
synonym: PD-0325901
synonym: PD0325901
synonym: PD 0325901
approved: f
ligand name: mirdametinib
type: SyntheticOrganicLigand

riviciclib
in ch i key: QLUYMIVVAYRECT-OCCSQVGLSA-N
in ch i: InChI=1S/C21H20ClNO5/c1-23-7-6-12(14(23)10-24)19-15(25)8-16(26)20-17(27)9-18(28-21(19)20)11-4-2-3-5-13(11)22/h2-5,8-9,12,14,24-26H,6-7,10H2,1H3/t12-,14+/m1/s1
comment: Riviciclib is a flavone based cyclin dependent kinase (CDK) inhibitor with potential antineoplastic activity <Reference id=26250/>.
iupac name: 2-(2-chlorophenyl)-5,7-dihydroxy-8-[(2R,3S)-2-(hydroxymethyl)-1-methylpyrrolidin-3-yl]chromen-4-one
synonym: P276-00
approved: f
ligand name: riviciclib
type: SyntheticOrganicLigand

sapanisertib
in ch i key: GYLDXIAOMVERTK-UHFFFAOYSA-N
in ch i: InChI=1S/C15H15N7O/c1-7(2)22-14-11(13(16)18-6-19-14)12(21-22)8-3-4-10-9(5-8)20-15(17)23-10/h3-7H,1-2H3,(H2,17,20)(H2,16,18,19)
comment: Sapanisertib (INK128) is an ATP-competitive inhibitor of mTOR in mTORC1 and mTORC2 complexes, that exhibits potent anti-tumour activity <Reference id=26246/><Reference id=26248/><Reference id=26249/>.
iupac name: 5-(4-amino-1-propan-2-ylpyrazolo[3,4-d]pyrimidin-3-yl)-1,3-benzoxazol-2-amine
synonym: TAK-228
synonym: MLN0128
synonym: INK 128
synonym: INK128
synonym: INK-128
approved: f
ligand name: sapanisertib
type: SyntheticOrganicLigand

amuvatinib
in ch i key: FOFDIMHVKGYHRU-UHFFFAOYSA-N
in ch i: InChI=1S/C23H21N5O3S/c32-23(24-12-15-5-6-18-19(11-15)30-14-29-18)28-9-7-27(8-10-28)22-21-20(25-13-26-22)16-3-1-2-4-17(16)31-21/h1-6,11,13H,7-10,12,14H2,(H,24,32)
comment: Amuvatinib is an orally bioavailable, multitargeted receptor tyrosine kinase inhibitor. Some bioactivity data may be associated with the hydrochloride salt (PubChem CID 67254077).
iupac name: N-(1,3-benzodioxol-5-ylmethyl)-4-([1]benzoxolo[2,3-e]pyrimidin-4-yl)piperazine-1-carbothioamide
xref: CHEMBL2103851
synonym: MP-470
synonym: MP 470
synonym: MP470
approved: f
ligand name: amuvatinib
type: SyntheticOrganicLigand

RTI-118
in ch i key: JJDDRYMIPIEXKX-UHFFFAOYSA-N
in ch i: InChI=1S/C26H32N4O3/c31-24(27-14-17-28-15-8-3-9-16-28)29-18-19-30-23(20-29)26(33-25(30)32,21-10-4-1-5-11-21)22-12-6-2-7-13-22/h1-2,4-7,10-13,23H,3,8-9,14-20H2,(H,27,31)
comment: RTI-118 is a small molecule antagonist of the neuropeptide S (NPS) receptor <Reference id=26229/>.
iupac name: 3-oxo-1,1-di(phenyl)-N-(2-piperidin-1-ylethyl)-5,6,8,8a-tetrahydro-[1,3]oxazolo[4,3-c]pyrazine-7-carboxamide
xref: CHEMBL470485
approved: f
ligand name: RTI-118
type: SyntheticOrganicLigand

PL37
in ch i key: BJCNUZJDFWFVBY-UHFFFAOYSA-N
in ch i: InChI=1S/C22H34N2O6S3/c1-4-28-22(27)30-16(2)29-20(25)13-24-21(26)18(12-17-8-6-5-7-9-17)14-32-33-15-19(23)10-11-31-3/h5-9,16,18-19H,4,10-15,23H2,1-3H3,(H,24,26)
comment: PL37 is an investigational, orally available, dual pro-drug inhibitor of neprilysin (a.k.a. neutral endopeptidase or NEP; MME) and aminopeptidase N (APN; ANPEP) <Reference id=30761/>. NEP and APN are enkephalin catabolising enzymes (or enkephalinases). Dual ENKephalinase inhibitors such as this one have been ascribed the acronym DENK inhibitor (or DENKi). PL37 is the non-stereo enantiomer of compound 15 in patent US8247609 <Reference id=30760/>. Such dual inhibitors are suggested as a novel mechanism for the control of central and peripheral pain <Reference id=30762/>, via inhibition of enzymatic degradation of endogenous enkephalins. Such agents could replace the use of opiate analgesics.
iupac name: 1-ethoxycarbonyloxyethyl 2-[[2-[(2-amino-4-methylsulfanylbutyl)disulfanylmethyl]-3-phenylpropanoyl]amino]acetate
synonym: Debio 0827
synonym: Debio-0827
synonym: 19-IIIa
approved: f
ligand name: PL37
type: SyntheticOrganicLigand

compound 6b [PMID: 24999562]
in ch i key: KAFZOLYKKCWUBI-HPMAGDRPSA-N
in ch i: InChI=1S/C40H72N12O8/c1-23(2)14-16-27(48-37(58)29(20-24(3)4)47-33(54)17-15-25-10-6-5-7-11-25)36(57)51-30(22-41)39(60)52-19-9-13-31(52)38(59)49-26(12-8-18-46-40(44)45)35(56)50-28(34(43)55)21-32(42)53/h23-31H,5-22,41H2,1-4H3,(H2,42,53)(H2,43,55)(H,47,54)(H,48,58)(H,49,59)(H,50,56)(H,51,57)(H4,44,45,46)/t26-,27-,28-,29-,30-,31-/m0/s1
comment: Derivative of NmU-C-terminal heptapeptide, selective NMU2 agonist.
approved: f
ligand name: compound 6b [PMID: 24999562]
type: PeptideLigand

compound 8d [PMID: 24999562]
in ch i key: HPJGEESDHAUUQR-SKGSPYGFSA-N
in ch i: InChI=1S/C51H67N15O8/c52-42(67)29-38(44(53)69)64-45(70)36(15-7-23-59-50(54)55)62-48(73)41-17-9-25-66(41)49(74)37(16-8-24-60-51(56)57)63-47(72)40(27-31-10-2-1-3-11-31)65-46(71)39(61-43(68)21-19-32-12-6-22-58-30-32)28-33-18-20-34-13-4-5-14-35(34)26-33/h1-6,10-14,18,20,22,26,30,36-41H,7-9,15-17,19,21,23-25,27-29H2,(H2,52,67)(H2,53,69)(H,61,68)(H,62,73)(H,63,72)(H,64,70)(H,65,71)(H4,54,55,59)(H4,56,57,60)/t36-,37-,38-,39-,40-,41-/m0/s1
comment: Derivative of NmU-C-terminal heptapeptide, selective NMU1 agonist.
approved: f
ligand name: compound 8d [PMID: 24999562]
type: PeptideLigand

BOMPPA
canonical SMILES: CCC(=O)NCCCc1cc(OC)ccc1Cc1cccc(c1)OC
isomeric SMILES: CCC(=O)NCCCc1cc(OC)ccc1Cc1cccc(c1)OC
in ch i key: GJRIGACGWLYZAO-UHFFFAOYSA-N
in ch i: InChI=1S/C21H27NO3/c1-4-21(23)22-12-6-8-17-15-20(25-3)11-10-18(17)13-16-7-5-9-19(14-16)24-2/h5,7,9-11,14-15H,4,6,8,12-13H2,1-3H3,(H,22,23)
xref: CHEMBL2326202
synonym: benzyloxy-methoxyphenyl-propylamide
synonym: compound 10 [PMID: 23228808]
approved: f
ligand name: BOMPPA
type: SyntheticOrganicLigand

UCM 765
canonical SMILES: COc1ccc(cc1)N(c1ccccc1)CCNC(=O)C
isomeric SMILES: COc1ccc(cc1)N(c1ccccc1)CCNC(=O)C
in ch i key: PWTCGLHUMIIRML-UHFFFAOYSA-N
in ch i: InChI=1S/C17H20N2O2/c1-14(20)18-12-13-19(15-6-4-3-5-7-15)16-8-10-17(21-2)11-9-16/h3-11H,12-13H2,1-2H3,(H,18,20)
iupac name: N-[2-[(4-methoxyphenyl)-phenylamino]ethyl]acetamide
xref: CHEMBL394676
synonym: UCM765
synonym: UCM-765
approved: f
ligand name: UCM 765
type: SyntheticOrganicLigand

isoamyl-agomelatine
canonical SMILES: COc1ccc2c(c1)c(CCNC(=O)C)cc(c2)CCC(C)C
isomeric SMILES: COc1ccc2c(c1)c(CCNC(=O)C)cc(c2)CCC(C)C
in ch i key: DGWFQLYAVLGONI-UHFFFAOYSA-N
in ch i: InChI=1S/C20H27NO2/c1-14(2)5-6-16-11-17-7-8-19(23-4)13-20(17)18(12-16)9-10-21-15(3)22/h7-8,11-14H,5-6,9-10H2,1-4H3,(H,21,22)
iupac name: N-[2-[7-methoxy-3-(3-methylbutyl)naphthalen-1-yl]ethyl]acetamide
xref: CHEMBL1946226
approved: f
ligand name: isoamyl-agomelatine
type: SyntheticOrganicLigand

(hydroxymethylphenyl)agomelatine
in ch i key: BHDVJMSEODZSTD-UHFFFAOYSA-N
in ch i: InChI=1S/C22H23NO3/c1-15(25)23-9-8-19-12-20(17-5-3-4-16(10-17)14-24)11-18-6-7-21(26-2)13-22(18)19/h3-7,10-13,24H,8-9,14H2,1-2H3,(H,23,25)
iupac name: N-[2-[3-[3-(hydroxymethyl)phenyl]-7-methoxynaphthalen-1-yl]ethyl]acetamide
xref: CHEMBL476131
synonym: compound 21 [PMID: 18778943]
approved: f
ligand name: (hydroxymethylphenyl)agomelatine
type: SyntheticOrganicLigand

binimetinib
in ch i key: ACWZRVQXLIRSDF-UHFFFAOYSA-N
comment: Binimetinib is a potent non-ATP competitive inhibitor of MEK1/2 kinase activity <Reference id=26201/> (link directly to abstract 794 online here).
iupac name: 6-[(4-bromo-2-fluorophenyl)amino]-7-fluoro-N-(2-hydroxyethoxy)-3-methylbenzimidazole-5-carboxamide
xref: CHEMBL3187723
synonym: MEK162
synonym: MEK-162
synonym: ARRY 162
synonym: ARRY-162
synonym: ARRY-438162
synonym: Mektovi®
approved: t
ligand name: binimetinib
type: SyntheticOrganicLigand

sabutoclax
in ch i key: RAYNZUHYMMLQQA-ZEQRLZLVSA-N
in ch i: InChI=1S/C42H40N2O8/c1-21-15-27-29(17-31(45)39(49)35(27)41(51)43-19-23(3)25-11-7-5-8-12-25)37(47)33(21)34-22(2)16-28-30(38(34)48)18-32(46)40(50)36(28)42(52)44-20-24(4)26-13-9-6-10-14-26/h5-18,23-24,45-50H,19-20H2,1-4H3,(H,43,51)(H,44,52)/t23-,24-/m0/s1
comment: BI-97C1 is a pan-active inhibitor of antiapoptotic B-cell lymphoma/leukemia-2 (Bcl-2) family proteins. Its discovery is described in <Reference id=26200/>, where it is compound 11. It is a derivative/analogue of <Ligand id=4204/>.
iupac name: 2,3,5-trihydroxy-7-methyl-N-[(2R)-2-phenylpropyl]-6-[1,6,7-trihydroxy-3-methyl-5-[[(2R)-2-phenylpropyl]carbamoyl]naphthalen-2-yl]naphthalene-1-carboxamide
xref: CHEMBL1094250
synonym: BI-97C1
synonym: BI 97C1
approved: f
ligand name: sabutoclax
type: SyntheticOrganicLigand

GNE-9605
in ch i key: PUXPEQJKNAWNQA-AAEUAGOBSA-N
comment: GNE-9605 is a highly potent and selective leucine-rich repeat kinase 2 (LRRK2) inhibitor <Reference id=26199/>. The compound is able to cross the blood-brain barrier identifying it as a potential lead in developing a novel disease-modifying Parkinson’s disease therapy.
iupac name: 2-N-[5-chloro-1-[(3S,4S)-3-fluoro-1-(oxetan-3-yl)piperidin-4-yl]pyrazol-4-yl]-4-N-methyl-5-(trifluoromethyl)pyrimidine-2,4-diamine
xref: CHEMBL3122117
synonym: GNE 9605
synonym: GNE9605
approved: f
ligand name: GNE-9605
type: SyntheticOrganicLigand

onvansertib
in ch i key: QHLVBNKYJGBCQJ-UHFFFAOYSA-N
in ch i: InChI=1S/C24H27F3N8O3/c1-33-6-8-34(9-7-33)15-3-5-18(38-24(25,26)27)17(12-15)30-23-29-13-14-2-4-16-20(22(28)37)32-35(10-11-36)21(16)19(14)31-23/h3,5,12-13,36H,2,4,6-11H2,1H3,(H2,28,37)(H,29,30,31)
comment: Onvansertib (NMS-P937) is an orally available, selective polo-like kinase 1 (PLK1) inhibitor. Its discovery is described in <Reference id=26198/>, where it is compound 7g.
iupac name: 1-(2-hydroxyethyl)-8-[5-(4-methylpiperazin-1-yl)-2-(trifluoromethoxy)anilino]-4,5-dihydropyrazolo[4,3-h]quinazoline-3-carboxamide
xref: CHEMBL1738758
synonym: NMS1286937
synonym: NMS-1286937
synonym: NMS P937
synonym: NMS-P937
approved: f
ligand name: onvansertib
type: SyntheticOrganicLigand

ESI-09
isomeric SMILES: N#C/C(=N/Nc1cccc(c1)Cl)/C(=O)c1noc(c1)C(C)(C)C
in ch i key: DXEATJQGQHDURZ-DEDYPNTBSA-N
in ch i: InChI=1S/C16H15ClN4O2/c1-16(2,3)14-8-12(21-23-14)15(22)13(9-18)20-19-11-6-4-5-10(17)7-11/h4-8,19H,1-3H3/b20-13+
comment: ESI-09 is a selective noncyclic nucleotide antagonist which can be used as a pharmacological probe of EPAC (exchange protein directly activated by cAMP) function <Reference id=26196/><Reference id=26197/>.
iupac name: 3-(5-tert-butylisoxazol-3-yl)-2-[(3-chlorophenyl)-hydrazono]-3-oxo-propionitrile
xref: CHEMBL3260990
synonym: ESI 09
synonym: ESI09
approved: f
ligand name: ESI-09
type: SyntheticOrganicLigand

santacruzamate A
canonical SMILES: CCOC(=O)NCCCC(=O)NCCc1ccccc1
isomeric SMILES: CCOC(=O)NCCCC(=O)NCCc1ccccc1
in ch i key: HTOYBIILVCHURC-UHFFFAOYSA-N
in ch i: InChI=1S/C15H22N2O3/c1-2-20-15(19)17-11-6-9-14(18)16-12-10-13-7-4-3-5-8-13/h3-5,7-8H,2,6,9-12H2,1H3,(H,16,18)(H,17,19)
comment: Santacruzamate A is a cytotoxin, isolated from a cyanobacterium resembling the genus Symploca. Chemically, it has structural features in similarity with the clinically approved histone deacetylase (HDAC) inhibitor <Ligand id=6852/> (aka SAHA), and like vorinostat, acts as a potent and selective HDAC inhibitor <Reference id=26195/>. It exhibits selectivity for the type I HDAC, HDAC2 compared to type II HDACs.
iupac name: ethyl N-[4-oxo-4-(2-phenylethylamino)butyl]carbamate
xref: CHEMBL3086767
synonym: CAY10683
approved: f
ligand name: santacruzamate A
type: SyntheticOrganicLigand

PFI-3
canonical SMILES: O=C(c1ccccc1O)C=CN1CC2CC1CN2c1ccccn1
isomeric SMILES: O=C(c1ccccc1O)/C=C/N1C[C@H]2C[C@@H]1CN2c1ccccn1
in ch i key: INAICWLVUAKEPB-QSTFCLMHSA-N
in ch i: InChI=1S/C19H19N3O2/c23-17-6-2-1-5-16(17)18(24)8-10-21-12-15-11-14(21)13-22(15)19-7-3-4-9-20-19/h1-10,14-15,23H,11-13H2/b10-8+/t14-,15-/m1/s1
comment: PFI-3 is a selective chemical probe for SMARCA bromodomains, including SMARCA2, SMARCA4 and PB1(5) (PBRM1) bromodomains. PFI-3 is one of the compounds contained in the Structural Genomics Consortium's Epigenetics Probes Collection. It's discovery, selectivity profile and pharmacological characterization is reported in <Reference id=30934/>.
iupac name: (E)-1-(2-hydroxyphenyl)-3-[(1R,4R)-2-pyridin-2-yl-2,5-diazabicyclo[2.2.1]heptan-5-yl]prop-2-en-1-one
synonym: PFI 3
synonym: IN2080
synonym: PF-06687252
synonym: compound 16 [PMID: 27115555]
approved: f
ligand name: PFI-3
type: SyntheticOrganicLigand

citalopram
canonical SMILES: N#Cc1ccc2c(c1)COC2(CCCN(C)C)c1ccc(cc1)F
isomeric SMILES: N#Cc1ccc2c(c1)COC2(CCCN(C)C)c1ccc(cc1)F
in ch i key: WSEQXVZVJXJVFP-UHFFFAOYSA-N
in ch i: InChI=1S/C20H21FN2O/c1-23(2)11-3-10-20(17-5-7-18(21)8-6-17)19-9-4-15(13-22)12-16(19)14-24-20/h4-9,12H,3,10-11,14H2,1-2H3
comment: The marketed formulation is a racemic mixture of stereo-isomers. We show the non-isomeric molecule to represent this mixture. The S enantiomer is known as <Ligand id=7177/>. R-citalopram has PubChem CID 6101829. Marketed formulations may contain citalopram hydrobromide (PubChem CID 77995).
iupac name: 1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-3H-2-benzofuran-5-carbonitrile
xref: CHEMBL549
synonym: LU-10171B
synonym: Celexa®
synonym: Cipramil®
approved: t
ligand name: citalopram
type: SyntheticOrganicLigand

USP7/USP47 inhibitor
in ch i key: GUDJFFQZIISQJB-UHFFFAOYSA-N
comment: Selective dual Inhibitor of the cancer-related deubiquitylating proteases USP7 (Q93009) and USP47 (Q96K76) <Reference id=30759/>.
iupac name: 4-cyano-5-(3,5-dichloropyridin-4-yl)sulfanyl-N-(4-methylsulfonylphenyl)thiophene-2-carboxamide
synonym: compound 14 [PMID: 24900381]
approved: f
ligand name: USP7/USP47 inhibitor
type: SyntheticOrganicLigand

BV-6
in ch i key: DPXJXGNXKOVBJV-YLOPQIBLSA-N
in ch i: InChI=1S/C70H96N10O8/c1-47(71-3)63(81)75-59(53-37-21-11-22-38-53)69(87)79-45-27-41-55(79)65(83)77-61(57(49-29-13-7-14-30-49)50-31-15-8-16-32-50)67(85)73-43-25-5-6-26-44-74-68(86)62(58(51-33-17-9-18-34-51)52-35-19-10-20-36-52)78-66(84)56-42-28-46-80(56)70(88)60(54-39-23-12-24-40-54)76-64(82)48(2)72-4/h7-10,13-20,29-36,47-48,53-62,71-72H,5-6,11-12,21-28,37-46H2,1-4H3,(H,73,85)(H,74,86)(H,75,81)(H,76,82)(H,77,83)(H,78,84)/t47-,48-,55-,56-,59-,60-,61-,62-/m0/s1
comment: BV-6 is a bivalent SMAC mimetic which acts as a dual cIAP and XIAP inhibitor <Reference id=26191/>.
synonym: BV6
approved: f
ligand name: BV-6
type: SyntheticOrganicLigand

filgotinib
in ch i key: RIJLVEAXPNLDTC-UHFFFAOYSA-N
in ch i: InChI=1S/C21H23N5O3S/c27-20(17-8-9-17)23-21-22-19-3-1-2-18(26(19)24-21)16-6-4-15(5-7-16)14-25-10-12-30(28,29)13-11-25/h1-7,17H,8-14H2,(H,23,24,27)
comment: Filgotinib is a selective and orally acive JAK1 inhibitor <Reference id=26190/>. It is being developed in a collaboration between Gilead Sciences and Galapagos for the treatment of inflammatory indications including psoriatic arthritis, ankylosing spondylitis, Crohn's disease, ulcerative colitis and rheumatoid arthritis. It is proposed as a once daily drug, that is predicted to cause fewer toxicity issues and adverse effects than existing JAK1 inhibitors.
iupac name: N-[5-[4-[(1,1-dioxo-1,4-thiazinan-4-yl)methyl]phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-yl]cyclopropanecarboxamide
xref: CHEMBL3301607
synonym: GLPG0634
synonym: Jyseleca®
synonym: GLPG-0634
approved: t
ligand name: filgotinib
type: SyntheticOrganicLigand

LCL161
in ch i key: UFPFGVNKHCLJJO-SSKFGXFMSA-N
in ch i: InChI=1S/C26H33FN4O3S/c1-16(28-2)24(33)30-22(17-7-4-3-5-8-17)26(34)31-14-6-9-21(31)25-29-20(15-35-25)23(32)18-10-12-19(27)13-11-18/h10-13,15-17,21-22,28H,3-9,14H2,1-2H3,(H,30,33)/t16-,21-,22-/m0/s1
comment: LCL161 is a SMAC mimetic which acts as an inhibitor of IAPs (inhibitor of apoptosis proteins), binding predominantly to their BIR3 domain <Reference id=26188/>. Use the following hyperlinks to view protein sequences for XIAP BIR3 and cIAP1 BIR3 provided by UniProt.org.
iupac name: (2S)-N-[(1S)-1-cyclohexyl-2-[(2S)-2-[4-(4-fluorobenzoyl)-1,3-thiazol-2-yl]pyrrolidin-1-yl]-2-oxoethyl]-2-methylaminopropanamide
xref: CHEMBL2431768
synonym: LCL-161
synonym: NVP-LCL161
approved: f
ligand name: LCL161
type: SyntheticOrganicLigand

HNHA
canonical SMILES: ONC(=O)CCCCCCSc1ccc2c(c1)cccc2
isomeric SMILES: ONC(=O)CCCCCCSc1ccc2c(c1)cccc2
in ch i key: KPNNXHVGOKRBEF-UHFFFAOYSA-N
in ch i: InChI=1S/C17H21NO2S/c19-17(18-20)9-3-1-2-6-12-21-16-11-10-14-7-4-5-8-15(14)13-16/h4-5,7-8,10-11,13,20H,1-3,6,9,12H2,(H,18,19)
comment: HNHA is a novel histone deacetylase (HDAC) inhibitor with potential anti-tumour and anti-liver fibrosis activity <Reference id=26187/><Reference id=26186/>.
iupac name: N-hydroxy-7-naphthalen-2-ylsulfanylheptanamide
xref: CHEMBL2419279
synonym: histone deacetylase inhibitor VI
approved: f
ligand name: HNHA
type: SyntheticOrganicLigand

creatine
canonical SMILES: OC(=O)CN(C(=N)N)C
isomeric SMILES: OC(=O)CN(C(=N)N)C
in ch i key: CVSVTCORWBXHQV-UHFFFAOYSA-N
in ch i: InChI=1S/C4H9N3O2/c1-7(4(5)6)2-3(8)9/h2H2,1H3,(H3,5,6)(H,8,9)
iupac name: 2-(1-methylcarbamimidamido)acetic acid
xref: CHEMBL283800
synonym: Cosmocair C 100
synonym: Creatin
synonym: Kreatin
synonym: Krebiozon
synonym: Phosphagen
synonym: Pyrolysate
approved: f
ligand name: creatine
type: MetaboliteLigand

defactinib
in ch i key: FWLMVFUGMHIOAA-UHFFFAOYSA-N
comment: Defactinib (VS-6063) is an orally bioavailable, second generation, small-molecule focal adhesion kinase (FAK) inhibitor with potential antiangiogenic and antineoplastic activities <Reference id=15289/><Reference id=26194/>. Phase 1 clinical trial results show that Defactinib is well tolerated and exhibits some clinical efficacy in patients (albeit in only two reported subjects) with advanced solid tumours <Reference id=36535/><Reference id=36536/>.
iupac name: N-methyl-4-((4-(((3-(N-methylmethylsulfonamido)pyrazin-2-yl)methyl)amino)-5-(trifluoromethyl)pyrimidin-2-yl)amino)benzamide
xref: CHEMBL3137331
synonym: VS-6063
synonym: PF-04554878
synonym: PF04554878
synonym: VS6063
approved: f
ligand name: defactinib
type: SyntheticOrganicLigand

gandotinib
in ch i key: SQSZANZGUXWJEA-UHFFFAOYSA-N
in ch i: InChI=1S/C23H25ClFN7O/c1-14-9-21(29-28-14)27-22-11-17(13-31-5-7-33-8-6-31)23-26-15(2)20(32(23)30-22)10-16-3-4-18(24)12-19(16)25/h3-4,9,11-12H,5-8,10,13H2,1-2H3,(H2,27,28,29,30)
comment: Gandotinib (LY2784544) is a potent ATP-competitive and selective JAK2 inhibitor <Reference id=26178/>, with potential clinical value for its ability to inhibit the constitutive activity of the JAK2V617F mutation found in myeloproliferative neoplasms (MPNs).
iupac name: 3-[(4-chloro-2-fluorophenyl)methyl]-2-methyl-N-(5-methyl-1H-pyrazol-3-yl)-8-(morpholin-4-ylmethyl)imidazo[1,2-b]pyridazin-6-amine
xref: CHEMBL2107823
synonym: LY-2784544
synonym: LY2784544
approved: f
ligand name: gandotinib
type: SyntheticOrganicLigand

encorafenib
in ch i key: CMJCXYNUCSMDBY-ZDUSSCGKSA-N
comment: Encorafenib (LGX-818) is an orally available BRAF kinase inhibitor with antineoplastic activity.
iupac name: methyl N-[(2S)-1-[[4-[3-[5-chloro-2-fluoro-3-(methanesulfonamido)phenyl]-1-propan-2-ylpyrazol-4-yl]pyrimidin-2-yl]amino]propan-2-yl]carbamate
xref: CHEMBL3301612
synonym: LGX818
synonym: LGX-818
synonym: Braftovi®
approved: t
ligand name: encorafenib
type: SyntheticOrganicLigand

7-hydroxystaurosporine
in ch i key: PBCZSGKMGDDXIJ-HQCWYSJUSA-N
in ch i: InChI=1S/C28H26N4O4/c1-28-25(35-3)15(29-2)12-18(36-28)31-16-10-6-4-8-13(16)19-21-22(27(34)30-26(21)33)20-14-9-5-7-11-17(14)32(28)24(20)23(19)31/h4-11,15,18,25,27,29,34H,12H2,1-3H3,(H,30,33)/t15-,18-,25-,27-,28+/m1/s1
comment: 7-hydroxystaurosporine is a cell-permeable <Ligand id=346/> derivative, with anticancer activity <Reference id=26172/>. It reversibly and ATP-competitively inhibits multiple protein kinases, including PKCα, β, γ, δ and ε <Reference id=26176/>, Chk1 <Reference id=26175/><Reference id=25819/><Reference id=26173/>, Cdc25C-associated protein kinase 1 (cTAK1) <Reference id=26175/>, Cdk1 <Reference id=25819/>, PAK4, Cdk5/p25, Chk2 <Reference id=26175/>, PDK1 <Reference id=26174/>, Lck <Reference id=25819/>, p38 MAPK kinase 2 (MAPK14) <Reference id=26173/>, Akt, GSK-3β <Reference id=25819/> and PKA <Reference id=26172/>.
xref: CHEMBL1236539
synonym: KRX-0601
synonym: KRX0601
synonym: UCN-01
synonym: UCN 01
approved: f
ligand name: 7-hydroxystaurosporine
type: SyntheticOrganicLigand

bafetinib
in ch i key: ZGBAJMQHJDFTQJ-DEOSSOPVSA-N
in ch i: InChI=1S/C30H31F3N8O/c1-19-4-7-23(13-27(19)39-29-36-10-8-26(38-29)22-14-34-18-35-15-22)37-28(42)20-5-6-21(25(12-20)30(31,32)33)16-41-11-9-24(17-41)40(2)3/h4-8,10,12-15,18,24H,9,11,16-17H2,1-3H3,(H,37,42)(H,36,38,39)/t24-/m0/s1
comment: Bafetinib is a second-generation, dual Lyn/Abl kinase inhibitor <Reference id=22938/><Reference id=32009/> with therapeutic.potential for the treatment of <Ligand id=5687/>-resistant or -intolerant B-cell chronic lymphocytic leukemia (CLL), and prostate cancer. Data indicate that bafetinib crosses the blood-brain-barrier, reaching therapeutic concentration, so the drug's potential for treatment of brain tumours is also under investigation. Note that we have mapped the chemical structure using the updated CAS registry number stipulated in INN proposed list 101 (2009) to the CID specified here, but the name maps to four other CIDs in PubChem.
iupac name: 4-[[(3S)-3-dimethylaminopyrrolidin-1-yl]methyl]-N-[4-methyl-3-[(4-pyrimidin-5-ylpyrimidin-2-yl)amino]phenyl]-3-(trifluoromethyl)benzamide
xref: CHEMBL206834
synonym: INNO-406
synonym: NS-187
synonym: Lyn-IN-1
approved: f
ligand name: bafetinib
type: SyntheticOrganicLigand

capmatinib
in ch i key: LIOLIMKSCNQPLV-UHFFFAOYSA-N
in ch i: InChI=1S/C23H17FN6O/c1-25-22(31)18-6-5-16(11-19(18)24)21-13-28-23-27-12-17(30(23)29-21)10-14-4-7-20-15(9-14)3-2-8-26-20/h2-9,11-13H,10H2,1H3,(H,25,31)
comment: Capmatinib (NCB28060) is a novel, oral, ATP-competitive inhibitor of c-MET that was developed by Novartis <Reference id=26166/>.
iupac name: 2-fluoro-N-methyl-4-[7-(quinolin-6-ylmethyl)imidazo[1,2-b][1,2,4]triazin-2-yl]benzamide
xref: CHEMBL3188267
synonym: INCB28060
synonym: INC280
synonym: Tabrecta®
approved: t
ligand name: capmatinib
type: SyntheticOrganicLigand

poziotinib
in ch i key: LPFWVDIFUFFKJU-UHFFFAOYSA-N
comment: Poziotinib is an orally bioavailable, clinically active, quinazoline-based pan epidermal growth factor receptor (EGFR or HER) inhibitor with antineoplastic activity <Reference id=26164/><Reference id=26165/>. It is a potent inhibitor of the most common EGFR and HER2 exon 20 insertion mutants that are predominantly activating in nature, and resistant to exisitng reversible and irreversible EGFR tyrosine kinase inhibitors <Reference id=39627/><Reference id=39628/>.
iupac name: 1-[4-[4-(3,4-dichloro-2-fluoroanilino)-7-methoxyquinazolin-6-yl]oxypiperidin-1-yl]prop-2-en-1-one
synonym: HM781-36B
synonym: NOV120101
approved: f
ligand name: poziotinib
type: SyntheticOrganicLigand

uprosertib
in ch i key: AXTAPYRUEKNRBA-JTQLQIEISA-N
comment: Uprosertib (GSK-2141795) is an inhibitor of the AKT family of protein kinases <Reference id=26162/>.
iupac name: N-[(2S)-1-amino-3-(3,4-difluorophenyl)propan-2-yl]-5-chloro-4-(4-chloro-2-methylpyrazol-3-yl)furan-2-carboxamide
xref: CHEMBL3137336
synonym: GSK-2141795
synonym: GSK2141795
approved: f
ligand name: uprosertib
type: SyntheticOrganicLigand

dapoxetine
canonical SMILES: CN(C(c1ccccc1)CCOc1cccc2c1cccc2)C
isomeric SMILES: CN([C@H](c1ccccc1)CCOc1cccc2c1cccc2)C
in ch i key: USRHYDPUVLEVMC-FQEVSTJZSA-N
in ch i: InChI=1S/C21H23NO/c1-22(2)20(18-10-4-3-5-11-18)15-16-23-21-14-8-12-17-9-6-7-13-19(17)21/h3-14,20H,15-16H2,1-2H3/t20-/m0/s1
comment: Dapoxetine hydrochloride (PubChem CID 71352) is the component used in marketed formulations.
iupac name: (1S)-N,N-dimethyl-3-naphthalen-1-yloxy-1-phenylpropan-1-amine
xref: CHEMBL2110900
synonym: LY-210448
synonym: LY 210448
synonym: Priligy
synonym: Extensil
synonym: Sustinex
synonym: Duratia
synonym: Pentenal-30
approved: t
ligand name: dapoxetine
type: SyntheticOrganicLigand

afegostat
canonical SMILES: OCC1CNCC(C1O)O
isomeric SMILES: OC[C@H]1CNC[C@H]([C@@H]1O)O
in ch i key: QPYJXFZUIJOGNX-HSUXUTPPSA-N
in ch i: InChI=1S/C6H13NO3/c8-3-4-1-7-2-5(9)6(4)10/h4-10H,1-3H2/t4-,5-,6-/m1/s1
iupac name: (3R,4R,5R)-5-(HYDROXYMETHYL)PIPERIDINE-3,4-DIOL
xref: CHEMBL206468
synonym: Plicera
synonym: isofagomine
synonym: iso-fagomine
approved: f
ligand name: afegostat
type: SyntheticOrganicLigand

RXP-407
in ch i key: OCAZUTUOYLAIOA-OSRSDYAFSA-N
in ch i: InChI=1S/C21H31N4O8P/c1-12(20(30)23-13(2)19(22)29)11-34(32,33)17(9-15-7-5-4-6-8-15)25-21(31)16(10-18(27)28)24-14(3)26/h4-8,12-13,16-17H,9-11H2,1-3H3,(H2,22,29)(H,23,30)(H,24,26)(H,25,31)(H,27,28)(H,32,33)/t12-,13+,16+,17-/m1/s1
comment: N-domain selective ACE inhibitor. This N-section corresponds to 30-630
iupac name: (3S)-3-acetamido-4-[[(1R)-1-[[(2S)-3-[[(2S)-1-amino-1-oxopropan-2-yl]amino]-2-methyl-3-oxopropyl]-hydroxyphosphoryl]-2-phenylethyl]amino]-4-oxobutanoic acid
xref: CHEMBL1235767
synonym: RXP 407
approved: f
ligand name: RXP-407
type: SyntheticOrganicLigand

lisinopril-tryptophan
in ch i key: JXNGDSIPMBNTNL-KMDXXIMOSA-N
in ch i: InChI=1S/C27H34N4O5/c28-15-7-6-12-22(30-23(26(33)34)14-13-18-8-2-1-3-9-18)25(32)31-24(27(35)36)16-19-17-29-21-11-5-4-10-20(19)21/h1-5,8-11,17,22-24,29-30H,6-7,12-16,28H2,(H,31,32)(H,33,34)(H,35,36)/t22-,23-,24+/m0/s1
comment: Lisinopril-tryptophan (LisW-S), an analogue of the ACE inhibitor lisinopril, is highly selective for the C-domain corresponding to 631-1232. Note there is a crystal structure for the ligand in 2X95 but in the Drosophila, not the human enzyme.
iupac name: (2S)-2-[[(2S)-6-amino-1-[[(1R)-1-carboxy-2-(1H-indol-3-yl)ethyl]amino]-1-oxohexan-2-yl]amino]-4-phenylbutanoic acid
approved: f
ligand name: lisinopril-tryptophan
type: SyntheticOrganicLigand

example 166 [WO2014154727]
in ch i key: SRVXSISGYBMIHR-UHFFFAOYSA-N
comment: Sanofi cathepsin A inhibitor.
iupac name: 3-[3-[3-(2-amino-2-oxoethyl)phenyl]-5-chlorophenyl]-3-(5-methyl-1,3-thiazol-2-yl)propanoic acid
approved: f
ligand name: example 166 [WO2014154727]
type: SyntheticOrganicLigand

compound 8a [PMID: 22861813]
in ch i key: DGGLFHJMXJUSDG-HNNXBMFYSA-N
in ch i: InChI=1S/C20H18FN3O4/c1-12-6-2-3-7-13(12)15(11-19(26)27)22-20(28)16-10-18(25)24(23-16)17-9-5-4-8-14(17)21/h2-10,15,23H,11H2,1H3,(H,22,28)(H,26,27)/t15-/m0/s1
comment: Cathepsin A inhibitor with PDB structure. Investigations indicated a pathophysiological role of CatA in cardiac hypertrophy and progression of a candidate into phase I clinical trials <Reference id=26135/>.
iupac name: (3S)-3-[[2-(2-fluorophenyl)-3-oxo-1H-pyrazole-5-carbonyl]amino]-3-(2-methylphenyl)propanoic acid
xref: CHEMBL3145341
approved: f
ligand name: compound 8a [PMID: 22861813]
type: SyntheticOrganicLigand

afuresertib
in ch i key: AFJRDFWMXUECEW-LBPRGKRZSA-N
comment: Afuresertib (GSK2110183) is an inhibitor of the AKT family of protein kinases <Reference id=26162/> in clincal trials for cancer. Note that in previous releases we had mistakenly linked the structure of GSK2141795 characterised in the same paper (PubChem CID 57826797) that has an extra fluorine in the terminal ring (n.b. several vendors in PubChem still have this name-to-structure error)
xref: CHEMBL2219422
synonym: GSK-2110183
synonym: GSK2110183
synonym: GSK 2110183
approved: f
ligand name: afuresertib
type: SyntheticOrganicLigand

entospletinib
in ch i key: XSMSNFMDVXXHGJ-UHFFFAOYSA-N
in ch i: InChI=1S/C23H21N7O/c1-2-17-14-25-28-20(17)13-16(1)21-15-30-8-7-24-23(30)22(27-21)26-18-3-5-19(6-4-18)29-9-11-31-12-10-29/h1-8,13-15H,9-12H2,(H,25,28)(H,26,27)
comment: Entospletinib is a highly selective and orally available Syk inhibitor. Its discovery (research code GS-9973) is described in <Reference id=26161/> where it is compound 68.
iupac name: 6-(1H-indazol-6-yl)-N-(4-morpholin-4-ylphenyl)imidazo[1,2-a]pyrazin-8-amine
xref: CHEMBL3265032
synonym: GS-9973
synonym: GS 9973
synonym: GS9973
approved: f
ligand name: entospletinib
type: SyntheticOrganicLigand

apitolisib
in ch i key: YOVVNQKCSKSHKT-HNNXBMFYSA-N
in ch i: InChI=1S/C23H30N8O3S/c1-14-17(13-29-3-5-31(6-4-29)22(33)15(2)32)35-19-18(14)27-20(16-11-25-23(24)26-12-16)28-21(19)30-7-9-34-10-8-30/h11-12,15,32H,3-10,13H2,1-2H3,(H2,24,25,26)/t15-/m0/s1
comment: Apitolisib is a dual PI3K/mTOR inhibitor. Its discovery is described in <Reference id=26156/>, where it is compound 2 (GDC-0980).
iupac name: (2S)-1-[4-[[2-(2-aminopyrimidin-5-yl)-7-methyl-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]piperazin-1-yl]-2-hydroxypropan-1-one
xref: CHEMBL1922094
synonym: GDC-0980
synonym: GDC0980
synonym: RG7422
synonym: RG-7422
approved: f
ligand name: apitolisib
type: SyntheticOrganicLigand

ipatasertib
in ch i key: GRZXWCHAXNAUHY-NSISKUIASA-N
in ch i: InChI=1S/C24H32ClN5O2/c1-15(2)26-13-19(17-4-6-18(25)7-5-17)24(32)30-10-8-29(9-11-30)23-21-16(3)12-20(31)22(21)27-14-28-23/h4-7,14-16,19-20,26,31H,8-13H2,1-3H3/t16-,19-,20-/m1/s1
comment: Ipatasertib is an inhibitor of the AKT family of protein kinases <Reference id=26155/>. The synthesis of ipatasertib is described in patent WO2008006040 <Reference id=26154/> and <Reference id=26155/> where it is compound 28 (the Supporting Information for this article contains activity data for compound 28 against a full kinase screening panel). This compound is also represented on PubChem by CID 23649210.
iupac name: (2S)-2-(4-chlorophenyl)-1-[4-[(5R,7R)-7-hydroxy-5-methyl-6,7-dihydro-5H-cyclopenta[e]pyrimidin-4-yl]piperazin-1-yl]-3-(propan-2-ylamino)propan-1-one
xref: CHEMBL2177390
synonym: GDC-0068
approved: f
ligand name: ipatasertib
type: SyntheticOrganicLigand

famitinib
isomeric SMILES: CCN(CCN1CCc2c(C1=O)c(C)c([nH]2)/C=C/1/C(=O)Nc2c1cc(F)cc2)CC
in ch i key: GKEYKDOLBLYGRB-LGMDPLHJSA-N
in ch i: InChI=1S/C23H27FN4O2/c1-4-27(5-2)10-11-28-9-8-19-21(23(28)30)14(3)20(25-19)13-17-16-12-15(24)6-7-18(16)26-22(17)29/h6-7,12-13,25H,4-5,8-11H2,1-3H3,(H,26,29)/b17-13-
comment: Famitinib is a multi-targeted receptor tyrosine kinase inhibitor <Reference id=26153/>. The compound is a structural analogue of <Ligand id=5713/>. The INN famitinib appeared in Proposed List 125 which was published by the WHO at the end of July 2021.
iupac name: 5-(2-diethylaminoethyl)-2-[(Z)-(5-fluoro-2-oxo-1H-indol-3-ylidene)methyl]-3-methyl-6,7-dihydro-1H-pyrrolo[4,5-c]pyridin-4-one
xref: CHEMBL1278146
synonym: SHR-1020
synonym: SHR1020
synonym: compound 9 [PMID: 21028894]
synonym: SHR 1020
approved: f
ligand name: famitinib
type: SyntheticOrganicLigand

ENMD-2076
isomeric SMILES: CN1CCN(CC1)c1nc(/C=C/c2ccccc2)nc(c1)Nc1n[nH]c(c1)C
in ch i key: BLQYVHBZHAISJM-CMDGGOBGSA-N
in ch i: InChI=1S/C21H25N7/c1-16-14-20(26-25-16)23-19-15-21(28-12-10-27(2)11-13-28)24-18(22-19)9-8-17-6-4-3-5-7-17/h3-9,14-15H,10-13H2,1-2H3,(H2,22,23,24,25,26)/b9-8+
comment: ENMD-2076 is an orally-active, Aurora A/angiogenic kinase inhibitor. It inhibits a distinct profile of angiogenic tyrosine kinases in addition to the Aurora A kinase. These angiogenic targets include VEGFR, Flt3 and FGFR3 kinases, which have been shown to play important roles in the pathology of several cancers.
iupac name: 6-(4-methylpiperazin-1-yl)-N-(5-methyl-1H-pyrazol-3-yl)-2-[(E)-2-phenylethenyl]pyrimidin-4-amine
xref: CHEMBL482968
synonym: ENMD2076
synonym: ENMD 2076
approved: f
ligand name: ENMD-2076
type: SyntheticOrganicLigand

ridaforolimus
in ch i key: BUROJSBIWGDYCN-GAUTUEMISA-N
in ch i: InChI=1S/C53H84NO14P/c1-32-18-14-13-15-19-33(2)44(63-8)30-40-23-21-38(7)53(61,67-40)50(58)51(59)54-25-17-16-20-41(54)52(60)66-45(35(4)28-39-22-24-43(46(29-39)64-9)68-69(11,12)62)31-42(55)34(3)27-37(6)48(57)49(65-10)47(56)36(5)26-32/h13-15,18-19,27,32,34-36,38-41,43-46,48-49,57,61H,16-17,20-26,28-31H2,1-12H3/b15-13+,18-14+,33-19+,37-27+/t32-,34-,35-,36-,38-,39+,40+,41+,43-,44+,45+,46-,48-,49+,53-/m1/s1
comment: Ridaforolimus is an investigational targeted and small-molecule inhibitor of the protein kinase mTOR <Reference id=26146/>. mTOR inhibition is hypothesised to provide maintenance therapy for patients with metastatic soft-tissue and bone sarcoma who generally have a poor prognosis despite receiving chemotherapy <Reference id=26145/>.
xref: CHEMBL2103839
synonym: deforolimus
synonym: AP-23573
synonym: AP23573
synonym: MK-8669
approved: f
ligand name: ridaforolimus
type: SyntheticOrganicLigand

trihexyphenidyl
canonical SMILES: OC(c1ccccc1)(C1CCCCC1)CCN1CCCCC1
isomeric SMILES: OC(c1ccccc1)(C1CCCCC1)CCN1CCCCC1
in ch i key: HWHLPVGTWGOCJO-UHFFFAOYSA-N
in ch i: InChI=1S/C20H31NO/c22-20(18-10-4-1-5-11-18,19-12-6-2-7-13-19)14-17-21-15-8-3-9-16-21/h1,4-5,10-11,19,22H,2-3,6-9,12-17H2
comment: Trihexyphenidyl is an antispasmodic, antimuscarinic drug. Marketed formulations may contain trihexyphenidyl hydrochloride (PubChem CID 66007).
iupac name: 1-cyclohexyl-1-phenyl-3-(piperidin-1-yl)propan-1-ol
xref: CHEMBL1490
synonym: Tremin
synonym: benzhexol
synonym: Artane®
synonym: Parkin
synonym: Pacitane
synonym: Apo-Trihex
approved: t
ligand name: trihexyphenidyl
type: SyntheticOrganicLigand

CP-724714
in ch i key: LLVZBTWPGQVVLW-SNAWJCMRSA-N
in ch i: InChI=1S/C27H27N5O3/c1-18-13-21(8-11-25(18)35-22-9-6-19(2)29-15-22)32-27-23-14-20(7-10-24(23)30-17-31-27)5-4-12-28-26(33)16-34-3/h4-11,13-15,17H,12,16H2,1-3H3,(H,28,33)(H,30,31,32)/b5-4+
comment: The discovery of CP-724714 is described in <Reference id=26143/>. The compound acts as a selective inhibitor of ERBB2 (HER2 epidermal growth factor receptor).
iupac name: 2-methoxy-N-[(E)-3-[4-[[3-methyl-4-(6-methylpyridin-3-yl)oxyphenyl]amino]quinazolin-6-yl]prop-2-enyl]acetamide
xref: CHEMBL483321
synonym: CP724714
synonym: CP 724714
approved: f
ligand name: CP-724714
type: SyntheticOrganicLigand

AZD0328
canonical SMILES: c1cnc2c(c1)CC1(O2)CN2CCC1CC2
isomeric SMILES: c1cnc2c(c1)C[C@]1(O2)CN2CCC1CC2
in ch i key: OCKIPDMKGPYYJS-ZDUSSCGKSA-N
in ch i: InChI=1S/C13H16N2O/c1-2-10-8-13(16-12(10)14-5-1)9-15-6-3-11(13)4-7-15/h1-2,5,11H,3-4,6-9H2/t13-/m0/s1
comment: AZD0328 is a nicotinic acetylcholine receptor alpha 7 (α7 nAChR) agonist. AZD0328 was developed as a potential treatment for the cognitive impairment associated with diseases such as schizophrenia and Alzheimer's disease. This compound is included in AstaZeneca's Open Innovation Pharmacology Toolbox.
iupac name: (8R)-spiro[1-azabicyclo[2.2.2]octane-8,2'-3H-furo[5,4-b]pyridine]
xref: CHEMBL2151437
synonym: AZD-0328
synonym: AZD 0328
approved: f
ligand name: AZD0328
type: SyntheticOrganicLigand

crenolanib
in ch i key: DYNHJHQFHQTFTP-UHFFFAOYSA-N
in ch i: InChI=1S/C26H29N5O2/c1-26(14-32-15-26)16-33-20-6-7-22-21(13-20)28-17-31(22)24-8-5-18-3-2-4-23(25(18)29-24)30-11-9-19(27)10-12-30/h2-8,13,17,19H,9-12,14-16,27H2,1H3
comment: Crenolanib (CP-868,596) is a potent and orally bioavailable benzamidazole Type I inhibitor of wild-type and mutant isoforms of the class III receptor tyrosine kinases FLT3 (FMS-like tyrosine kinase 3), PDGFRα (platelet-derived growth factor receptor), and PDGFRβ <Reference id=36435/><Reference id=26144/><Reference id=36434/>. It preferentially binds to phosphorylated active kinases in the 'DFG in' conformation.
iupac name: 1-[2-[5-[(3-methyloxetan-3-yl)methoxy]benzimidazol-1-yl]quinolin-8-yl]piperidin-4-amine
xref: CHEMBL2105728
synonym: CP 868596
synonym: CP-868596
synonym: ARO-002
synonym: CP-868,596
approved: f
ligand name: crenolanib
type: SyntheticOrganicLigand

CP-547632
in ch i key: HXHAJRMTJXHJJZ-UHFFFAOYSA-N
comment: CP-547632 is a potent inhibitor of VEGFR2 and basic fibroblast growth factor (FGF) receptor kinases <Reference id=26140/>.
iupac name: 3-[(4-bromo-2,6-difluorophenyl)methoxy]-5-(4-pyrrolidin-1-ylbutylcarbamoylamino)-1,2-thiazole-4-carboxamide
xref: CHEMBL253969
synonym: CP 547,632
synonym: CP-547,632
synonym: CP 547632
synonym: CP547632
approved: f
ligand name: CP-547632
type: SyntheticOrganicLigand

agerafenib
in ch i key: DKNUPRMJNUQNHR-UHFFFAOYSA-N
in ch i: InChI=1S/C24H22F3N5O5/c1-23(2,24(25,26)27)19-11-20(32-37-19)31-22(33)30-13-6-5-7-14(8-13)36-21-15-9-17(34-3)18(35-4)10-16(15)28-12-29-21/h5-12H,1-4H3,(H2,30,31,32,33)
comment: The discovery and synthesis of agerafenib (CEP-32496) is described in <Reference id=26138/> where it is compound 40. Agerafenib is an orally bioavailable B-Raf proto-oncogene, serine/threonine kinase (BRAF) inhibitor with potential antineoplastic activity, which selectively inhibits the activity of the mutated form (V600E) of BRAF kinase <Reference id=26138/><Reference id=36208/>.
iupac name: 1-[3-(6,7-dimethoxyquinazolin-4-yl)oxyphenyl]-3-[5-(1,1,1-trifluoro-2-methylpropan-2-yl)-1,2-oxazol-3-yl]urea
xref: CHEMBL2029988
synonym: CEP32496
synonym: AC013773
synonym: CEP-32496
synonym: RXDX-105
synonym: CEP 32496
approved: f
ligand name: agerafenib
type: SyntheticOrganicLigand

BMS-690514
in ch i key: CSGQVNMSRKWUSH-IAGOWNOFSA-N
in ch i: InChI=1S/C19H24N6O2/c1-27-15-4-2-3-14(9-15)23-19-18-13(5-8-25(18)22-12-21-19)10-24-7-6-16(20)17(26)11-24/h2-5,8-9,12,16-17,26H,6-7,10-11,20H2,1H3,(H,21,22,23)/t16-,17-/m1/s1
comment: BMS-690514 is a potent inhibitor of human epidermal growth factor (EGF) receptors EGFR, HER2 and HER4 and vascular endothelial growth factor receptors (VEGFRs) 1-3 <Reference id=26136/><Reference id=26137/>.
iupac name: (3R,4R)-4-amino-1-[[4-[(3-methoxyphenyl)amino]pyrrolo[2,1-f][1,2,4]triazin-5-yl]methyl]piperidin-3-ol
synonym: BMS 690514
synonym: BMS690514
approved: f
ligand name: BMS-690514
type: SyntheticOrganicLigand

buparlisib
in ch i key: CWHUFRVAEUJCEF-UHFFFAOYSA-N
in ch i: InChI=1S/C18H21F3N6O2/c19-18(20,21)13-9-15(22)23-11-12(13)14-10-16(26-1-5-28-6-2-26)25-17(24-14)27-3-7-29-8-4-27/h9-11H,1-8H2,(H2,22,23)
comment: The discovery of buparlisib is described in <Reference id=26128/> where it is compound 15. Buparlisib is a selective and orally bioavailable phosphoinositide 3-kinase (PI3K) inhibitor <Reference id=26128/><Reference id=26133/>.
iupac name: 5-[2,6-di(morpholin-4-yl)pyrimidin-4-yl]-4-(trifluoromethyl)pyridin-2-amine
xref: CHEMBL2017974
synonym: BKM120
synonym: BKM 120
synonym: BKM-120
synonym: NVP-BKM120
approved: f
ligand name: buparlisib
type: SyntheticOrganicLigand

myo-inositol
canonical SMILES: OC1C(O)C(O)C(C(C1O)O)O
in ch i key: CDAISMWEOUEBRE-GPIVLXJGSA-N
in ch i: InChI=1S/C6H12O6/c7-1-2(8)4(10)6(12)5(11)3(1)9/h1-12H/t1-,2-,3-,4+,5-,6-
comment: PubChem CID 892 shows the non-chiral inositol structure
iupac name: (1R,2R,3r,4S,5S,6s)-cyclohexane-1,2,3,4,5,6-hexol
xref: CHEMBL1222251
synonym: D-myo-inositol
approved: f
ligand name: myo-inositol
type: MetaboliteLigand

infigratinib
in ch i key: QADPYRIHXKWUSV-UHFFFAOYSA-N
comment: The discovery and synthesis of infigratinib (BGJ-398) is described in <Reference id=26125/>, where it is compound 1h. It is an orally bioavailable, ATP-competitive pan inhibitor of human fibroblast growth factor receptors (FGFRs) with potential antiangiogenic and antineoplastic activities <Reference id=26125/>.
iupac name: 3-(2,6-dichloro-3,5-dimethoxyphenyl)-1-[6-[4-(4-ethylpiperazin-1-yl)anilino]pyrimidin-4-yl]-1-methylurea
xref: CHEMBL1852688
synonym: BGJ398
synonym: BGJ 398
synonym: NVP-BGJ398
synonym: BGJ-398
synonym: Truseltiq®
approved: t
ligand name: infigratinib
type: SyntheticOrganicLigand

boceprevir
in ch i key: LHHCSNFAOIFYRV-DOVBMPENSA-N
in ch i: InChI=1S/C27H45N5O5/c1-25(2,3)20(30-24(37)31-26(4,5)6)23(36)32-13-15-17(27(15,7)8)18(32)22(35)29-16(19(33)21(28)34)12-14-10-9-11-14/h14-18,20H,9-13H2,1-8H3,(H2,28,34)(H,29,35)(H2,30,31,37)/t15-,16?,17-,18-,20+/m0/s1
comment: Boceprevir is an active site-binding inhibitor of the main protease (nonstructural protein 3, NS3) of hepatitis C virus (HCV). A patent claims boceprevir for repurposing as a cathepsin A modulator <Reference id=26142/>. More recently it has been reported to inhibit the 3CL protease (Mpro) of several coronaviruses, including SARS-CoV-2 Mpro <Reference id=39404/><Reference id=41381/>. An alternative enantiomer is reported in the SARS-CoV-2 Mpro/boceprevir crystal structure 6WNP, which maps to PubChem CID 71316139.
iupac name: (1R,2S,5S)-N-(4-amino-1-cyclobutyl-3,4-dioxobutan-2-yl)-3-[(2S)-2-(tert-butylcarbamoylamino)-3,3-dimethylbutanoyl]-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxamide
xref: CHEMBL218394
synonym: SCH-503034
synonym: EBP520
synonym: EBP-520
synonym: SCH503034
synonym: Victrelis®
approved: t
ligand name: boceprevir
type: SyntheticOrganicLigand

copanlisib
in ch i key: MWYDSXOGIBMAET-UHFFFAOYSA-N
in ch i: InChI=1S/C23H28N8O4/c1-33-19-17(35-10-2-6-30-8-11-34-12-9-30)4-3-16-18(19)28-23(31-7-5-25-20(16)31)29-21(32)15-13-26-22(24)27-14-15/h3-4,13-14,25H,2,5-12H2,1H3,(H2,24,26,27)
comment: Copanlisib is a phosphoinositide 3-kinase (PI3K) inhibitor <Reference id=26124/>, preferentially inhibiting PI3Kα and PI3Kβ, and with significant antineoplastic activity <Reference id=26123/>. The compound has less potent mTOR activity.
iupac name: 2-amino-N-[7-methoxy-8-(3-morpholin-4-ylpropoxy)-2,3-dihydro-1H-imidazo[1,2-c]quinazolin-5-ylidene]pyrimidine-5-carboxamide
xref: CHEMBL3218576
synonym: Aliqopa®
synonym: BAY 80-6946
synonym: BAY80-6946
approved: t
ligand name: copanlisib
type: SyntheticOrganicLigand

roniciclib
in ch i key: UELYDGOOJPRWGF-MFOHZAOFSA-N
comment: Roniciclib is an orally bioavailable cyclin dependent kinase (CDK) inhibitor with potential antineoplastic activity, with selectively for CDK1/cyclin B, CDK2/cyclin E, CDK4/cyclin D1, and CDK9/cyclin T1, which play key roles in the regulation of cell cycle progression and cellular proliferation <Reference id=26121/><Reference id=26122/>.
synonym: BAY 1000394
synonym: KB-145902
synonym: BAY 10-00394
approved: f
ligand name: roniciclib
type: SyntheticOrganicLigand

picropodophyllin
in ch i key: YJGVMLPVUAXIQN-HAEOHBJNSA-N
in ch i: InChI=1S/C22H22O8/c1-25-16-4-10(5-17(26-2)21(16)27-3)18-11-6-14-15(30-9-29-14)7-12(11)20(23)13-8-28-22(24)19(13)18/h4-7,13,18-20,23H,8-9H2,1-3H3/t13-,18+,19+,20-/m0/s1
comment: Picropodophyllin is a lignan extract from podophyllin resin produced in the roots of podophyllum plants. It is an epimer of picropodophyllotoxin. Picropodophyllin has been suggested to act as a selective inhibitor of the insulin-like growth factor 1 receptor (IGF1R) and has potential antineoplastic activity <Reference id=26118/><Reference id=26119/>. Its effect via IGF1R have been questioned <Reference id=26120/>.
iupac name: (5R,5aR,8aS,9R)-5-hydroxy-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-8-one
xref: CHEMBL283120
synonym: podofilox
synonym: AXL1717
approved: f
ligand name: picropodophyllin
type: SyntheticOrganicLigand

pimasertib
canonical SMILES: OCC(CNC(=O)c1ccncc1Nc1ccc(cc1F)I)O
isomeric SMILES: OC[C@H](CNC(=O)c1ccncc1Nc1ccc(cc1F)I)O
in ch i key: VIUAUNHCRHHYNE-JTQLQIEISA-N
in ch i: InChI=1S/C15H15FIN3O3/c16-12-5-9(17)1-2-13(12)20-14-7-18-4-3-11(14)15(23)19-6-10(22)8-21/h1-5,7,10,20-22H,6,8H2,(H,19,23)/t10-/m0/s1
comment: Pimasertib is an orally bioavailable small-molecule inhibitor of the mitogen-activated protein kinases MEK1 and MEK2 (MEK1/2) with potential antineoplastic activity <Reference id=26115/>. It binds to an allosteric site, distinct from the ATP binding site <Reference id=26116/> and as such prevents activation rather than inhibiting catalysis.
iupac name: N-[(2S)-2,3-dihydroxypropyl]-3-(2-fluoro-4-iodoanilino)pyridine-4-carboxamide
xref: CHEMBL2107832
synonym: AS703026
synonym: MSC1936369B
synonym: AS-703026
approved: f
ligand name: pimasertib
type: SyntheticOrganicLigand

telaprevir
in ch i key: BBAWEDCPNXPBQM-GDEBMMAJSA-N
in ch i: InChI=1S/C36H53N7O6/c1-5-10-25(29(44)34(48)39-23-15-16-23)40-33(47)28-24-14-9-13-22(24)20-43(28)35(49)30(36(2,3)4)42-32(46)27(21-11-7-6-8-12-21)41-31(45)26-19-37-17-18-38-26/h17-19,21-25,27-28,30H,5-16,20H2,1-4H3,(H,39,48)(H,40,47)(H,41,45)(H,42,46)/t22-,24-,25-,27-,28-,30+/m0/s1
comment: Inhibits the hepatitis C viral enzyme NS3.4A serine protease but also has a recent repurposing claim for cathepsin A inhibition <Reference id=26139/>.
iupac name: (1S,3aR,6aS)-2-[(2S)-2-[[(2S)-2-cyclohexyl-2-(pyrazine-2-carbonylamino)acetyl]amino]-3,3-dimethylbutanoyl]-N-[(3S)-1-(cyclopropylamino)-1,2-dioxohexan-3-yl]-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrole-1-carboxamide
xref: CHEMBL231813
synonym: VX-950
approved: f
ligand name: telaprevir
type: SyntheticOrganicLigand

compound 1 [PMID: 24900526]
canonical SMILES: OC(=O)CNS(=O)(=O)c1ccc(cc1)c1ccccc1
isomeric SMILES: OC(=O)CNS(=O)(=O)c1ccc(cc1)c1ccccc1
in ch i key: ZIAFXLGSGMQYPL-UHFFFAOYSA-N
in ch i: InChI=1S/C14H13NO4S/c16-14(17)10-15-20(18,19)13-8-6-12(7-9-13)11-4-2-1-3-5-11/h1-9,15H,10H2,(H,16,17)
comment: MMP12 inhibitor (compound 1) from predrug <Ligand id=7868/> converted to prodrug <Ligand id=7869/> <Reference id=26424/>
iupac name: 2-[(4-phenylphenyl)sulfonylamino]acetic acid
xref: CHEMBL1335679
synonym: compound 1 [PMID: 24900526]
approved: f
ligand name: compound 1 [PMID: 24900526]
type: SyntheticOrganicLigand

HPTE
canonical SMILES: ClC(C(c1ccc(cc1)O)c1ccc(cc1)O)(Cl)Cl
isomeric SMILES: ClC(C(c1ccc(cc1)O)c1ccc(cc1)O)(Cl)Cl
in ch i key: IUGDILGOLSSKNE-UHFFFAOYSA-N
in ch i: InChI=1S/C14H11Cl3O2/c15-14(16,17)13(9-1-5-11(18)6-2-9)10-3-7-12(19)8-4-10/h1-8,13,18-19H
iupac name: 4-[2,2,2-trichloro-1-(4-hydroxyphenyl)ethyl]phenol
xref: CHEMBL196585
approved: f
ligand name: HPTE
type: SyntheticOrganicLigand

example 92 [WO2012095521]
in ch i key: NQNLROFWOGGJGK-SFHVURJKSA-N
comment: This compound is a BACE2 inhibitor and is example 92 from Novartis' patent WO2012095521, which has 274 examples in the result tables. See also the BACE2 patent review <Reference id=22366/>.
iupac name: N-[3-[(3R)-5-amino-3-(fluoromethyl)-2,6-dihydro-1,4-oxazin-3-yl]-4-fluorophenyl]-5-chloro-3-methylpyridine-2-carboxamide
approved: f
ligand name: example 92 [WO2012095521]
type: SyntheticOrganicLigand

compound 5 [PMID: 24900526]
in ch i key: QXROXWFFCFLRBZ-ZEQRLZLVSA-N
in ch i: InChI=1S/C28H35N3O9S/c1-19(2)16-23(27(35)31(17-25(32)33)41(37,38)22-13-11-21(39-3)12-14-22)29-26(34)24-10-7-15-30(24)28(36)40-18-20-8-5-4-6-9-20/h4-6,8-9,11-14,19,23-24H,7,10,15-18H2,1-3H3,(H,29,34)(H,32,33)/t23-,24-/m0/s1
comment: Prodrug from <Ligand id=7868/>.
iupac name: 2-[(4-methoxyphenyl)sulfonyl-[(2S)-4-methyl-2-[[(2S)-1-phenylmethoxycarbonylpyrrolidine-2-carbonyl]amino]pentanoyl]amino]acetic acid
xref: CHEMBL2205660
approved: f
ligand name: compound 5 [PMID: 24900526]
type: SyntheticOrganicLigand

compound 3 [PMID: 24900526]
in ch i key: XGNIOZCAZTWXMZ-WCHFFXHOSA-N
in ch i: InChI=1S/C52H68N8O15S/c1-31(2)27-40(49(69)57-39(23-25-45(64)65)48(68)56-38(22-24-44(62)63)47(67)54-33(5)46(53)66)55-43(61)29-60(76(73,74)37-20-18-36(19-21-37)35-15-10-7-11-16-35)51(71)41(28-32(3)4)58-50(70)42-17-12-26-59(42)52(72)75-30-34-13-8-6-9-14-34/h6-11,13-16,18-21,31-33,38-42H,12,17,22-30H2,1-5H3,(H2,53,66)(H,54,67)(H,55,61)(H,56,68)(H,57,69)(H,58,70)(H,62,63)(H,64,65)/t33-,38-,39-,40-,41-,42-/m0/s1
comment: This is an MMP12-specific peptide sequence with the active inhibitor released upon enzyme cleavage as a three-step conversion predrug (this entry) > prodrug <Ligand id=7869/> > drug <Ligand id=7870/> <Reference id=26424/>
iupac name: (4S)-5-[[(2S)-1-amino-1-oxopropan-2-yl]amino]-4-[[(2S)-4-carboxy-2-[[(2S)-4-methyl-2-[[2-[[(2S)-4-methyl-2-[[(2S)-1-phenylmethoxycarbonylpyrrolidine-2-carbonyl]amino]pentanoyl]-(4-phenylphenyl)sulfonylamino]acetyl]amino]pentanoyl]amino]butanoyl]amino]-5-oxopentanoic acid
xref: CHEMBL2205657
approved: f
ligand name: compound 3 [PMID: 24900526]
type: SyntheticOrganicLigand

XNT [PMID: 18391097]
in ch i key: SEVKFSGZVZFIMA-UHFFFAOYSA-N
in ch i: InChI=1S/C25H26N2O6S/c1-16-4-8-19(9-5-16)34(30,31)33-18-7-11-22-20(14-18)24(29)23-21(26-12-13-27(2)3)10-6-17(15-28)25(23)32-22/h4-11,14,26,28H,12-13,15H2,1-3H3
comment: ACE2 activator that decreases blood pressure in hypertensive rats.
iupac name: [8-(2-dimethylaminoethylamino)-5-(hydroxymethyl)-9-oxoxanthen-2-yl] 4-methylbenzenesulfonate
approved: f
ligand name: XNT [PMID: 18391097]
type: SyntheticOrganicLigand

clonidine
canonical SMILES: Clc1cccc(c1NC1=NCCN1)Cl
isomeric SMILES: Clc1cccc(c1NC1=NCCN1)Cl
in ch i key: GJSURZIOUXUGAL-UHFFFAOYSA-N
in ch i: InChI=1S/C9H9Cl2N3/c10-6-2-1-3-7(11)8(6)14-9-12-4-5-13-9/h1-3H,4-5H2,(H2,12,13,14)
comment: Clonidine is an α2 adrenoceptor agonist. The structure shown here is in the amino form. A tautomeric imino form, represented by CHEBI:3757 also exists.
iupac name: N-(2,6-dichlorophenyl)-4,5-dihydro-1H-imidazol-2-amine
xref: CHEMBL134
synonym: Catapres-TTS
synonym: Adesipress
synonym: Catapresan
synonym: Catarpres-TTS
synonym: Clonidin
synonym: Catarpres
synonym: Catarpresan
synonym: Clonistada
synonym: Dixarit
synonym: Duraclon
synonym: Duraclont
synonym: Ipotensium
synonym: Isoglaucon
synonym: Tenso-Timelets
synonym: Catapressan
synonym: Catapres®
synonym: Kapvay&reg
approved: t
ligand name: clonidine
type: SyntheticOrganicLigand

MLN-4760
in ch i key: NTCCRGGIJNDEAB-IRXDYDNUSA-N
comment: ACE2 inhibitor used for animal functional studies.
iupac name: (2S)-2-[[(2S)-3-[3-[(3,5-dichlorophenyl)methyl]imidazol-4-yl]-1-hydroxy-1-oxopropan-2-yl]amino]-4-methylpentanoic acid
xref: CHEMBL429844
synonym: MLN4760
synonym: MLN 4760
approved: f
ligand name: MLN-4760
type: SyntheticOrganicLigand

bisphenol A
canonical SMILES: CC(c1ccc(cc1)O)(c1ccc(cc1)O)C
isomeric SMILES: CC(c1ccc(cc1)O)(c1ccc(cc1)O)C
in ch i key: IISBACLAFKSPIT-UHFFFAOYSA-N
in ch i: InChI=1S/C15H16O2/c1-15(2,11-3-7-13(16)8-4-11)12-5-9-14(17)10-6-12/h3-10,16-17H,1-2H3
comment: Bisphenol A acts as an estrogen mimic <Reference id=26104/><Reference id=26105/> and may also have anti-androgenic activity <Reference id=26107/>.
iupac name: 4-[2-(4-hydroxyphenyl)propan-2-yl]phenol
xref: CHEMBL418971
synonym: BPA
approved: f
ligand name: bisphenol A
type: SyntheticOrganicLigand

compound 30 [PMID: 23414845]
in ch i key: AVFJKWOKOZKXRX-UHFFFAOYSA-N
in ch i: InChI=1S/C22H26N4O2S/c1-22(2,3)16-8-6-15(7-9-16)13-23-17-10-11-19-18(12-17)21-20(14-24-25(21)4)29(27,28)26(19)5/h6-12,14,23H,13H2,1-5H3
comment: Compound 30 <Reference id=19834/> is a selective inhibitor of the tyrosine kinase PTK2 (aka FAK). It is a type III inhibitor, meaning that it binds to an allosteric site, not to the ATP active site of the kinase.
iupac name: N-[(4-tert-butylphenyl)methyl]-1,5-dimethyl-4,4-dioxopyrazolo[4,3-c][2,1]benzothiazin-8-amine
xref: CHEMBL2333444
approved: f
ligand name: compound 30 [PMID: 23414845]
type: SyntheticOrganicLigand

gabexate
canonical SMILES: CCOC(=O)c1ccc(cc1)OC(=O)CCCCCN=C(N)N
isomeric SMILES: CCOC(=O)c1ccc(cc1)OC(=O)CCCCCN=C(N)N
in ch i key: YKGYIDJEEQRWQH-UHFFFAOYSA-N
in ch i: InChI=1S/C16H23N3O4/c1-2-22-15(21)12-7-9-13(10-8-12)23-14(20)6-4-3-5-11-19-16(17)18/h7-10H,2-6,11H2,1H3,(H4,17,18,19)
comment: Gabexate (as the mesylate) is an inhibitor of trypsin-like serine proteases and is used in the treatment of pancreatitis, disseminated intravascular coagulation and as a regional anticoagulant for hemodialysis. The mesylate is PubChem CID 6604561.
iupac name: ethyl 4-[6-(diaminomethylideneamino)hexanoyloxy]benzoate
xref: CHEMBL87563
approved: t
ligand name: gabexate
type: SyntheticOrganicLigand

relacatib
in ch i key: BWYBBMQLUKXECQ-GIVPXCGWSA-N
in ch i: InChI=1S/C27H32N4O6S/c1-17(2)14-21(30-27(34)24-15-19-8-4-5-9-23(19)37-24)26(33)29-20-12-11-18(3)31(16-22(20)32)38(35,36)25-10-6-7-13-28-25/h4-10,13,15,17-18,20-21H,11-12,14,16H2,1-3H3,(H,29,33)(H,30,34)/t18-,20+,21+/m1/s1
comment: Relacatib is a cathepsin K inhibitor, developed by GlaxoSmithKline and selected for clinical development in osteoporosis.
iupac name: N-[(2S)-4-methyl-1-[[(4S,7R)-7-methyl-3-oxo-1-pyridin-2-ylsulfonylazepan-4-yl]amino]-1-oxopentan-2-yl]-1-benzofuran-2-carboxamide
xref: CHEMBL203665
synonym: SB462795
synonym: SB-462795
approved: f
ligand name: relacatib
type: SyntheticOrganicLigand

balicatib
in ch i key: LLCRBOWRJOUJAE-UHFFFAOYSA-N
in ch i: InChI=1S/C23H33N5O2/c1-2-14-27-15-17-28(18-16-27)20-8-6-19(7-9-20)21(29)26-23(10-4-3-5-11-23)22(30)25-13-12-24/h6-9H,2-5,10-11,13-18H2,1H3,(H,25,30)(H,26,29)
comment: Balicatib is an inhibitor of cathepsin K developed by Novartis.
iupac name: N-[1-(cyanomethylcarbamoyl)cyclohexyl]-4-(4-propylpiperazin-1-yl)benzamide
xref: CHEMBL371064
synonym: AAE581
approved: f
ligand name: balicatib
type: SyntheticOrganicLigand

L873724
in ch i key: VYFDSJLOCIGIKP-SFTDATJTSA-N
comment: This compound is a specific cathepsin K inhibitor <Reference id=26111/> (compound 22 in the article), which is used as a functional probe in studying the effects of cathepsin K inhibition.
xref: CHEMBL437501
synonym: L-873724
approved: f
ligand name: L873724
type: SyntheticOrganicLigand

B3C
in ch i key: KGNDCEVUMONOKF-UGPLYTSKSA-N
in ch i: InChI=1S/C44H51N5O8/c1-30-19-21-33(22-20-30)28-55-34-26-37(40(50)48-39(18-10-11-25-45)44(53,54)42-46-35-16-8-9-17-38(35)57-42)49(27-34)41(51)36(24-23-31-12-4-2-5-13-31)47-43(52)56-29-32-14-6-3-7-15-32/h2-9,12-17,19-22,34,36-37,39,53-54H,10-11,18,23-29,45H2,1H3,(H,47,52)(H,48,50)/t34-,36-,37+,39+/m1/s1
comment: This compound was developed by Novartis Institute as an inhibitor of protease, serine, 8 (PRSS8/prostasin), which acts as an activator of the epithelial sodium channel ENa. Inhibition of such activators may target cystic fibrosis <Reference id=26091/>. 257 analogues are included in patent WO2007137080, but without inhibition data.
iupac name: benzyl N-[(2R)-1-[(2S,4R)-2-[[(2S)-6-amino-1-(1,3-benzoxazol-2-yl)-1,1-dihydroxyhexan-2-yl]carbamoyl]-4-[(4-methylphenyl)methoxy]pyrrolidin-1-yl]-1-oxo-4-phenylbutan-2-yl]carbamate
synonym: compound 23 [PMID: 18752942]
approved: f
ligand name: B3C
type: SyntheticOrganicLigand

sacubitrilat
in ch i key: DOBNVUFHFMVMDB-BEFAXECRSA-N
in ch i: InChI=1S/C22H25NO5/c1-15(22(27)28)13-19(23-20(24)11-12-21(25)26)14-16-7-9-18(10-8-16)17-5-3-2-4-6-17/h2-10,15,19H,11-14H2,1H3,(H,23,24)(H,25,26)(H,27,28)/t15-,19+/m1/s1
comment: This compound is a neprilysin (MME-membrane metallo-endopeptidase) inhibitor generated from the prodrug <Ligand id=7857/>. Sacubitril is a component of the approved fixed-dose combination drug Entresto® (sacubitril plus <Ligand id=3937/>). The chemical database relationships are detailed in this blogpost.
iupac name: (2R,4S)-4-[(4-hydroxy-4-oxobutanoyl)amino]-2-methyl-5-(4-phenylphenyl)pentanoic acid
xref: CHEMBL417007
synonym: LBQ-657
synonym: LBQ657
approved: f
ligand name: sacubitrilat
type: SyntheticOrganicLigand

sacubitril
in ch i key: PYNXFZCZUAOOQC-UTKZUKDTSA-N
in ch i: InChI=1S/C24H29NO5/c1-3-30-24(29)17(2)15-21(25-22(26)13-14-23(27)28)16-18-9-11-20(12-10-18)19-7-5-4-6-8-19/h4-12,17,21H,3,13-16H2,1-2H3,(H,25,26)(H,27,28)/t17-,21+/m1/s1
comment: Sacubitril is a prodrug activated by de-ethylation via esterases to the neprilysin inhibitor <Ligand id=7858/>. Neprilysin is also known as neutral endopeptidase (NEP), and its official gene symbol is MME (membrane metallo-endopeptidase ). The chemical database relationships are detailed in this blogpost. Sabucatril is a component of the approved fixed mixture Entresto®, previously known as LCZ696, and which is now approved for heart failure (see Clinical data tab).
iupac name: 4-[[(2S,4R)-5-ethoxy-4-methyl-5-oxo-1-(4-phenylphenyl)pentan-2-yl]amino]-4-oxobutanoic acid
xref: CHEMBL3137301
synonym: AHU377
synonym: Entresto®
synonym: Neparvis®
approved: t
ligand name: sacubitril
type: SyntheticOrganicLigand

example 41 [WO2012028563]
in ch i key: GUOONOJYWQOJJP-DCMFLLSESA-N
comment: This compound is a potent BACE2 inhibitor and is example 41 from patent WO2012028563 <Reference id=26088/>, which includes IC50s for 75 BACE2 inhibitor compounds. See also BACE2 patent review <Reference id=22366/>.
approved: f
ligand name: example 41 [WO2012028563]
type: SyntheticOrganicLigand

compound J [PMID: 21907142]
in ch i key: VVZZZUNCWSTIOI-KRWDZBQOSA-N
comment: First published reports of this compound described it as a BACE1 inhibitor, but it was later identified as a BACE2 inhibitor as example 1 (with IC50 9 nM) from patent WO2011029803 <Reference id=26086/>. It is also published as compound J from the BACE2 diabetes target paper <Reference id=26087/>.
iupac name: N-[3-[(4S)-2-amino-4-methyl-5,6-dihydro-1,3-thiazin-4-yl]-4-fluorophenyl]-5-chloropyridine-2-carboxamide
xref: CHEMBL2347211
synonym: Example 1 (WO2011029803)
approved: f
ligand name: compound J [PMID: 21907142]
type: SyntheticOrganicLigand

example 20 [WO2010128058]
in ch i key: VZUGBLTVBZJZOE-KRWDZBQOSA-N
in ch i: InChI=1S/C17H17ClN6O2/c1-17(7-13(25)24(2)16(19)23-17)10-4-3-5-12(6-10)22-15(26)14-20-8-11(18)9-21-14/h3-6,8-9H,7H2,1-2H3,(H2,19,23)(H,22,26)/t17-/m0/s1
comment: This compound is a BACE2 inhibitor developed by Roche, and is example 20 (out of 130) in patent WO2010128058 <Reference id=26085/>. See also BACE2 patent review <Reference id=22366/>.
iupac name: N-[3-[(4S)-2-amino-1,4-dimethyl-6-oxo-5H-pyrimidin-4-yl]phenyl]-5-chloropyrimidine-2-carboxamide
approved: f
ligand name: example 20 [WO2010128058]
type: SyntheticOrganicLigand

example 2 [WO2013004676]
in ch i key: COCAUCFPFHUGAA-MGNBDDOMSA-N
comment: This compound is a BACE1 or BACE2 inhibitor, and is example 2 from patent WO2013004676 <Reference id=26083/> (with 8 examples tested). Also published as patent review <Reference id=26084/>. This is more potent against BACE2 even although the patent is focused on BACE1 for Alzheimer's disease (AD).
iupac name: N-[3-[(1S,7S)-5-amino-4-thia-6-azabicyclo[5.1.0]oct-5-en-7-yl]-4-fluorophenyl]-5-chloropyridine-2-carboxamide
xref: CHEMBL2331712
synonym: entry 2 [PMID: 24900681]
approved: f
ligand name: example 2 [WO2013004676]
type: SyntheticOrganicLigand

(R)-flurbiprofen
canonical SMILES: OC(=O)C(c1ccc(c(c1)F)c1ccccc1)C
isomeric SMILES: OC(=O)[C@@H](c1ccc(c(c1)F)c1ccccc1)C
in ch i key: SYTBZMRGLBWNTM-SNVBAGLBSA-N
in ch i: InChI=1S/C15H13FO2/c1-10(15(17)18)12-7-8-13(14(16)9-12)11-5-3-2-4-6-11/h2-10H,1H3,(H,17,18)/t10-/m1/s1
comment: Tarenflurbil or R-flurbiprofen, is the single enantiomer of the racemate NSAID <Ligand id=4194/>. Research and trials for Alzheimer's disease were conducted by Myriad Genetics but the company discontinued development in 2008. This compound is the archetypal γ-secretase modulator (GSM) that blocks γ-secretase cleavage of amyloid-β protein precursor (AβPP) to generate the longer, 42-residue amyloid-β (Aβ42) without changing the production of total Aβ (e.g. CHF5074) <Reference id=23969/>.
iupac name: (2R)-2-(3-fluoro-4-phenylphenyl)propanoic acid
xref: CHEMBL190083
synonym: MPC-7869
approved: f
ligand name: (R)-flurbiprofen
type: SyntheticOrganicLigand

Org27569
in ch i key: AHFZDNYNXFMRFQ-UHFFFAOYSA-N
in ch i: InChI=1S/C24H28ClN3O/c1-2-20-21-16-18(25)8-11-22(21)27-23(20)24(29)26-13-12-17-6-9-19(10-7-17)28-14-4-3-5-15-28/h6-11,16,27H,2-5,12-15H2,1H3,(H,26,29)
iupac name: 5-chloro-3-ethyl-N-[2-(4-piperidin-1-ylphenyl)ethyl]-1H-indole-2-carboxamide
xref: CHEMBL1553629
synonym: Org 27569
approved: f
ligand name: Org27569
type: SyntheticOrganicLigand

SSR128129E
in ch i key: SNMCWIDCSPHZRD-UHFFFAOYSA-N
in ch i: InChI=1S/C18H16N2O4/c1-10-15(20-8-4-3-5-14(20)17(10)24-2)16(21)11-6-7-13(19)12(9-11)18(22)23/h3-9H,19H2,1-2H3,(H,22,23)
comment: SSR128129E is commonly used as the sodium salt (PubChem CID 68853159, CAS number 848318-25-2) and any bioactivity data likely relates to this salt form.
iupac name: 2-amino-5-(1-methoxy-2-methylindolizine-3-carbonyl)benzoic acid
synonym: SSR
approved: f
ligand name: SSR128129E
type: SyntheticOrganicLigand

andarine
in ch i key: YVXVTLGIDOACBJ-SFHVURJKSA-N
in ch i: InChI=1S/C19H18F3N3O6/c1-11(26)23-12-3-6-14(7-4-12)31-10-18(2,28)17(27)24-13-5-8-16(25(29)30)15(9-13)19(20,21)22/h3-9,28H,10H2,1-2H3,(H,23,26)(H,24,27)/t18-/m0/s1
comment: Andarine is a nonsteroidal selective androgen receptor modulator, with agonist activity <Reference id=14297/>, via interaction with the orthosteric pocket of the receptor.
iupac name: (2S)-3-(4-acetamidophenoxy)-2-hydroxy-2-methyl-N-[4-nitro-3-(trifluoromethyl)phenyl]propanamide
xref: CHEMBL125236
synonym: GTX007
synonym: GTX-007
approved: f
ligand name: andarine
type: SyntheticOrganicLigand

CGP13501
in ch i key: XGWATTXMMMANFJ-UHFFFAOYSA-N
in ch i: InChI=1S/C19H30O2/c1-17(2,3)14-9-13(11-19(7,8)12-20)10-15(16(14)21)18(4,5)6/h9-10,12,21H,11H2,1-8H3
comment: CGP13501 is a positive allosteric modulator of GABAB Class C GPCRs <Reference id=3436/> which potentiates GABA-induced GTPγ[35S] binding, but displays no intrinsic agonist activity.
iupac name: 3-(3,5-ditert-butyl-4-hydroxyphenyl)-2,2-dimethylpropanal
xref: CHEMBL1256746
synonym: CGP 13501
synonym: CGP-13501
approved: f
ligand name: CGP13501
type: SyntheticOrganicLigand

LUF6200
in ch i key: DNTKZECWRGSWKD-UHFFFAOYSA-N
in ch i: InChI=1S/C18H21N3O5/c1-2-19(12-11-15-3-5-16(6-4-15)20(22)23)13-14-26-18-9-7-17(8-10-18)21(24)25/h3-10H,2,11-14H2,1H3
comment: The chemical structure shown here was drawn from <Reference id=26078/>. LUF6200 acts as an inhibitory allosteric modulator of the human ether-à-go-go (hERG) K+ channel, with respect to <Ligand id=2603/> and <Ligand id=2604/>, but displays positive co-operativity with K+ ions <Reference id=26078/>.
iupac name: ethyl[2-(4-nitrophenoxy)ethyl][2-(4-nitrophenyl)ethyl]amine
approved: f
ligand name: LUF6200
type: SyntheticOrganicLigand

TCN-201
in ch i key: FYIBXBFDXNPBSF-UHFFFAOYSA-N
comment: TCN-201 is compound 1 in <Reference id=22923/>. TCN-201 is a potent negative allosteric modulator of glycine but not glutamate at GluN2A NMDA receptors <Reference id=22925/>.
iupac name: N-[[4-[(benzoylamino)carbamoyl]phenyl]methyl]-3-chloro-4-fluorobenzenesulfonamide
xref: CHEMBL2333945
synonym: QCR-22
synonym: TCN 201
synonym: TCN201
approved: f
ligand name: TCN-201
type: SyntheticOrganicLigand

QNZ 46
canonical SMILES: COC1=CC2C(=NC(=[N+](C2=O)c2ccc(cc2)C(=O)O)C=Cc2cccc(c2)[N+](=O)[O-])C=C1
isomeric SMILES: COC1=CC2C(=NC(=[N+](C2=O)c2ccc(cc2)C(=O)O)/C=C/c2cccc(c2)[N+](=O)[O-])C=C1
in ch i key: ZLXASDKCRPAANV-LFYBBSHMSA-O
in ch i: InChI=1S/C24H17N3O6/c1-33-19-10-11-21-20(14-19)23(28)26(17-8-6-16(7-9-17)24(29)30)22(25-21)12-5-15-3-2-4-18(13-15)27(31)32/h2-14,20H,1H3/p+1/b12-5+
comment: QNZ 46 is a negative allosteric modulator of the GluN2C/D NMDA receptor inhibiting receptor function more potently when glutamate (but not glycine) is present <Reference id=26074/>.
iupac name: 4-[6-methoxy-2-[(E)-2-(3-nitrophenyl)ethenyl]-4-oxo-4aH-quinazolin-3-ium-3-yl]benzoic acid
synonym: KB-275239
approved: f
ligand name: QNZ 46
type: SyntheticOrganicLigand

AZD1236
in ch i key: SFJFBTPHDHUUPU-OAHLLOKOSA-N
comment: AZD1236 is a selective MMP-9 and MMP-12 inhibitor (IC50 4.5 and 6.1nM) from Astrazeneca that, since it failed biomarker endpoints for COPD is included in the AZ Open Innovation 2014 set for repurposing. Pending any published link the structure identification is tenatative but seems likely to be the structure crystalised in WO2007106022.
iupac name: (5S)-5-[[4-(5-chloropyridin-2-yl)oxypiperidin-1-yl]sulfonylmethyl]-5-methylimidazolidine-2,4-dione
synonym: AZD 1236
synonym: AZD-1236
approved: f
ligand name: AZD1236
type: SyntheticOrganicLigand

DQP-1105
in ch i key: ACUGSRUCGXYFTL-UHFFFAOYSA-N
in ch i: InChI=1S/C29H24BrN3O4/c1-17-7-12-22-21(15-17)27(19-5-3-2-4-6-19)28(29(37)31-22)23-16-24(18-8-10-20(30)11-9-18)33(32-23)25(34)13-14-26(35)36/h2-12,15,24,28H,13-14,16H2,1H3,(H,35,36)
comment: DQP-1105 is a negative allosteric modulator of the GluN2C/D NMDA receptor inhibiting receptor function more potently when glutamate (but not glycine) is present <Reference id=26072/>.
iupac name: 4-[3-(4-bromophenyl)-5-(6-methyl-2-oxo-4-phenyl-3H-quinolin-3-yl)-3,4-dihydropyrazol-2-yl]-4-oxobutanoic acid
synonym: KB-272091
approved: f
ligand name: DQP-1105
type: SyntheticOrganicLigand

CX614
canonical SMILES: O=C1N2CCCC2Oc2c1cc1OCCOc1c2
isomeric SMILES: O=C1N2CCCC2Oc2c1cc1OCCOc1c2
in ch i key: RQEPVMAYUINZRE-UHFFFAOYSA-N
in ch i: InChI=1S/C13H13NO4/c15-13-8-6-10-11(17-5-4-16-10)7-9(8)18-12-2-1-3-14(12)13/h6-7,12H,1-5H2
comment: CX614 is a positive allosteric modulator of the AMPA receptor <Reference id=26071/> with respect to AMPA.
xref: CHEMBL599662
synonym: CX 614
synonym: BDP 37
synonym: CX-614
approved: f
ligand name: CX614
type: SyntheticOrganicLigand

BMS-582949
in ch i key: GDTQLZHHDRRBEB-UHFFFAOYSA-N
in ch i: InChI=1S/C22H26N6O2/c1-4-9-23-22(30)17-11-28-19(14(17)3)20(24-12-25-28)27-18-10-15(6-5-13(18)2)21(29)26-16-7-8-16/h5-6,10-12,16H,4,7-9H2,1-3H3,(H,23,30)(H,26,29)(H,24,25,27)
comment: BMS-582949 is an inhibitor of p38 mitogen-activated protein kinase (MAPK). Its discovery is described in <Reference id=26054/>.
iupac name: 4-[[5-(cyclopropylcarbamoyl)-2-methylphenyl]amino]-5-methyl-N-propylpyrrolo[5,1-f][1,2,4]triazine-6-carboxamide
xref: CHEMBL1230065
synonym: BMS 582949
synonym: PS-540446
synonym: PS 540446
synonym: BMS582949
synonym: PS540446
approved: f
ligand name: BMS-582949
type: SyntheticOrganicLigand

spebrutinib
in ch i key: KXBDTLQSDKGAEB-UHFFFAOYSA-N
in ch i: InChI=1S/C22H22FN5O3/c1-3-20(29)25-16-5-4-6-17(13-16)26-21-19(23)14-24-22(28-21)27-15-7-9-18(10-8-15)31-12-11-30-2/h3-10,13-14H,1,11-12H2,2H3,(H,25,29)(H2,24,26,27,28)
comment: Spebrutinib acts as an inhibitor of Bruton's tyrosine kinase (BTK).
iupac name: N-[3-[[5-fluoro-2-[4-(2-methoxyethoxy)anilino]pyrimidin-4-yl]amino]phenyl]prop-2-enamide
xref: CHEMBL3301625
synonym: cc-292
synonym: AVL 292
synonym: AVL-292
approved: f
ligand name: spebrutinib
type: SyntheticOrganicLigand

E6201
isomeric SMILES: CCNc1cc2/C=C/C[C@H](O)[C@H](O)C(=O)/C=C/[C@H]([C@@H](OC(=O)c2c(c1)O)C)C
in ch i key: MWUFVYLAWAXDHQ-HMNLTAHHSA-N
in ch i: InChI=1S/C21H27NO6/c1-4-22-15-10-14-6-5-7-16(23)20(26)17(24)9-8-12(2)13(3)28-21(27)19(14)18(25)11-15/h5-6,8-13,16,20,22-23,25-26H,4,7H2,1-3H3/b6-5+,9-8-/t12-,13+,16+,20+/m1/s1
comment: The discovery of E6201 is described in <Reference id=26049/>. It is a fully synthetic analogue of the naturally occurring fungal resorcylic lactone LL-Z1640-2 (PubChem CID 9863776).
iupac name: (4S,5R,6Z,9S,10S,12E)-16-ethylamino-9,10,18-trihydroxy-4,5-dimethyl-3-oxabicyclo[12.4.0]octadeca-1(14),6,12,15,17-pentaene-2,8-dione
xref: CHEMBL1097999
synonym: E 6201
synonym: E-6201
approved: f
ligand name: E6201
type: SyntheticOrganicLigand

losmapimod
in ch i key: KKYABQBFGDZVNQ-UHFFFAOYSA-N
in ch i: InChI=1S/C22H26FN3O2/c1-13-17(9-15(10-18(13)23)21(28)26-16-6-7-16)19-8-5-14(11-24-19)20(27)25-12-22(2,3)4/h5,8-11,16H,6-7,12H2,1-4H3,(H,25,27)(H,26,28)
comment: Losmapimod is a p38 mitogen-activated kinase α/β inhibitor. It was originally developed by GlaxoSmithKline for cardiovascular disease, but this failed to show efficacy. Fulcrum acquired the drug and are repurposing it for the treatment of the progressive muscle wasting disorder facioscapulohumeral muscular dystrophy (FSHD) based on evidence that p38α regulates expression of the FSHD-related gene DUX4 <Reference id=40168/><Reference id=40169/>.
iupac name: 6-[5-(cyclopropylcarbamoyl)-3-fluoro-2-methylphenyl]-N-(2,2-dimethylpropyl)pyridine-3-carboxamide
xref: CHEMBL1088752
synonym: GW856553
synonym: GS856553
approved: f
ligand name: losmapimod
type: SyntheticOrganicLigand

TL-77
isomeric SMILES: COc1cc(OC)c(c(c1)OC)/C=C/S(=O)(=O)Cc1cnc(c(c1)NS(=O)(=O)C)OC
in ch i key: HEBBDGMHRHUJRY-VOTSOKGWSA-N
in ch i: InChI=1S/C19H24N2O8S2/c1-26-14-9-17(27-2)15(18(10-14)28-3)6-7-31(24,25)12-13-8-16(21-30(5,22)23)19(29-4)20-11-13/h6-11,21H,12H2,1-5H3/b7-6+
comment: The discovery of the TL-77, is described in <Reference id=26043/> (and also as compound 9a in <Reference id=26046/>). This compound is reported to have improved oral bioavailability compared to <Ligand id=7833/>, and represents a lead anti-mitotic, anti-cancer agent with potential for further development.
xref: CHEMBL3261266
approved: f
ligand name: TL-77
type: SyntheticOrganicLigand

rigosertib
isomeric SMILES: COc1cc(OC)cc(c1/C=C/S(=O)(=O)Cc1ccc(c(c1)NCC(=O)O)OC)OC
in ch i key: OWBFCJROIKNMGD-BQYQJAHWSA-N
in ch i: InChI=1S/C21H25NO8S/c1-27-15-10-19(29-3)16(20(11-15)30-4)7-8-31(25,26)13-14-5-6-18(28-2)17(9-14)22-12-21(23)24/h5-11,22H,12-13H2,1-4H3,(H,23,24)/b8-7+
comment: Rigosertib is a dual kinase inhibitor, affecting the phosphoinositide 3-kinase (PI3K) and polo-like kinase 1 (PLK1) pathways. Note that the inhibitory action on PLK1 has been disputed <Reference id=26044/>. It is a non-ATP-competitive inhibitor, meaning it inhibits substrate binding to the enzyme. Note that some bioactivity data may be associated with the sodium salt, PubChem CID 23696523.
iupac name: 2-[[2-methoxy-5-[[(E)-2-(2,4,6-trimethoxyphenyl)ethenyl]sulfonylmethyl]phenyl]amino]acetic acid
xref: CHEMBL1241855
synonym: ON-01910
synonym: Estybon® (proposed trade name)
synonym: ON01910.Na
approved: f
ligand name: rigosertib
type: SyntheticOrganicLigand

compound 23n [PMID: 24900877]
in ch i key: PUQLADUSPHHAJY-CQOQZXRMSA-N
in ch i: InChI=1S/C32H36N2O4/c1-3-23-6-4-5-7-28(23)33-32(37)34-20-21(2)38-30-19-27(16-17-29(30)34)26-14-12-25(13-15-26)24-10-8-22(9-11-24)18-31(35)36/h4-7,12-17,19,21-22,24H,3,8-11,18,20H2,1-2H3,(H,33,37)(H,35,36)/t21-,22-,24-/m1/s1
comment: The discovery of compound 23n is described in <Reference id=26040/>. Compound 23n is an inhibitor of diacylglycerol O-acyltransferase 1 (DGAT1) being investigated as a potential treatment for obesity. PubChem CID 86277844 represents ths molecule wih alternative stereochemisrty.
iupac name: 2-[(1r,4r)-4-{4-[(2R)-4-[(2-ethylphenyl)carbamoyl]-2-methyl-3,4-dihydro-2H-1,4-benzoxazin-7-yl]phenyl}cyclohexyl]acetic acid
xref: CHEMBL3287898
approved: f
ligand name: compound 23n [PMID: 24900877]
type: SyntheticOrganicLigand

compound 5B [PMID: 25349648]
in ch i key: MCFBUIIRFZBRCU-RZDIXWSQSA-N
in ch i: InChI=1S/C25H27F3N4O3/c26-25(27,28)17-4-7-20-21(13-17)31-23(30-20)16-3-8-22(29-14-16)32-11-9-19(10-12-32)35-18-5-1-15(2-6-18)24(33)34/h3-4,7-8,13-15,18-19H,1-2,5-6,9-12H2,(H,30,31)(H,33,34)/t15-,18-
comment: The discovery of compound 5B is described in <Reference id=26037/>. This compound is an inhibitor of diacylglycerol O-acyltransferase 1 (DGAT1) and is being investigated as a potential treatment for obesity. PubChem CID 71078515 represents ths molecule wih no specified stereochemisrty.
iupac name: (1r,4r)-4-[(1-{5-[5-(trifluoromethyl)-1H-1,3-benzodiazol-2-yl]pyridin-2-yl}piperidin-4-yl)oxy]cyclohexane-1-carboxylic acid
approved: f
ligand name: compound 5B [PMID: 25349648]
type: SyntheticOrganicLigand

pradigastat
in ch i key: GXALXAKNHIROPE-QAQDUYKDSA-N
in ch i: InChI=1S/C25H24F3N3O2/c26-25(27,28)23-12-10-21(15-30-23)31-20-9-11-22(29-14-20)19-7-5-18(6-8-19)17-3-1-16(2-4-17)13-24(32)33/h5-12,14-17,31H,1-4,13H2,(H,32,33)/t16-,17-
comment: Pradigastat is a potent and selective inhibitor of diacylglycerol O-acyltransferase 1 (DGAT1). The PubChem CID 53387035 shows the molecule with no stereochemistry.
iupac name: 2-{4-[4-(5-{[6-(trifluoromethyl)pyridin-3-yl]amino}pyridin-2-yl)phenyl]cyclohexyl}acetic acid
xref: CHEMBL2364624
synonym: LCQ908
synonym: LCQ-908
approved: f
ligand name: pradigastat
type: SyntheticOrganicLigand

PF-04620110
in ch i key: GEVVQZHMFVFGLN-HDJSIYSDSA-N
in ch i: InChI=1S/C21H24N4O4/c22-19-18-20(24-12-23-19)29-10-9-25(21(18)28)16-7-5-15(6-8-16)14-3-1-13(2-4-14)11-17(26)27/h5-8,12-14H,1-4,9-11H2,(H,26,27)(H2,22,23,24)/t13-,14-
comment: PF-04620110 is a potent and selective inhibitor of diacylglycerol O-acyltransferase 1 (DGAT1) <Reference id=26027/> and was developed as a potential treatment for obesity. PubChem CID 46926360 shows the flat molecule without stereochemistry.
iupac name: 2-[(1r,4r)-4-(4-{4-amino-5-oxo-5H,6H,7H,8H-pyrimido[5,4-f][1,4]oxazepin-6-yl}phenyl)cyclohexyl]acetic acid
xref: CHEMBL1835919
approved: f
ligand name: PF-04620110
type: SyntheticOrganicLigand

T863
in ch i key: FUIYMYNYUHVDPT-HDJSIYSDSA-N
in ch i: InChI=1S/C22H26N4O3/c1-22(2)19(26-18-20(23)24-12-25-21(18)29-22)16-9-7-15(8-10-16)14-5-3-13(4-6-14)11-17(27)28/h7-10,12-14H,3-6,11H2,1-2H3,(H,27,28)(H2,23,24,25)/t13-,14-
comment: T863 is an investigational inhibitor of diacylglycerol O-acyltransferase 1 (DGAT1) and was tested pre-clinically as a potential treatment for obesity. Development appears not to have progressed to clinical trials. PubChem CID 9865421 represents the flat molecule without stereochemistry.
iupac name: trans-4-[4-(4-Amino-7,7-dimethyl-7H-pyrimido[4,5-b][1,4]oxazin-6-yl)phenyl]cyclohexaneacetic acid
xref: CHEMBL473967
approved: f
ligand name: T863
type: SyntheticOrganicLigand

AZD7687
in ch i key: YXFNPRHZMOGREC-SHTZXODSSA-N
in ch i: InChI=1S/C21H25N3O3/c1-12-19(24-20(21(22)27)13(2)23-12)17-9-7-16(8-10-17)15-5-3-14(4-6-15)11-18(25)26/h7-10,14-15H,3-6,11H2,1-2H3,(H2,22,27)(H,25,26)/t14-,15-
comment: AZD7687 is a potent and selective inhibtor of diacylglycerol O-acyltransferase 1 (DGAT1). This compound was in the AstraZeneca/MRC repurposing list from 2011. PubChem CID 42636350 represents ths molecule wih no specified stereochemisrty.
xref: CHEMBL2178953
synonym: AZD 7687
synonym: AZD-7687
approved: f
ligand name: AZD7687
type: SyntheticOrganicLigand

AZD9056
in ch i key: HSQAARMBHJCUOK-UHFFFAOYSA-N
in ch i: InChI=1S/C24H35ClN2O2/c25-22-5-4-17(3-1-6-26-7-2-8-28)12-21(22)23(29)27-16-24-13-18-9-19(14-24)11-20(10-18)15-24/h4-5,12,18-20,26,28H,1-3,6-11,13-16H2,(H,27,29)
comment: AZD9056 is a potent, selective, orally bioavailable P2X7 receptor antagonist. This compound was in the AstraZeneca/NCATS repurposing list from 2012.
iupac name: N-(1-adamantylmethyl)-2-chloro-5-[3-(3-hydroxypropylamino)propyl]benzamide
synonym: AZD-9056
synonym: AZD 9056
approved: f
ligand name: AZD9056
type: SyntheticOrganicLigand

AZD2423
in ch i key: WERHXSXPOAOBJV-QGZVFWFLSA-N
comment: AZD2423 is a non-competitive negative allosteric modulator of the chemokine receptor CCR2. See the slideset presented by John G Cumming at the 17th RSC/SCI Medicinal Chemistry Symposium, 9th September, 2013, Churchill College, Cambridge <Reference id=26019/> for further details of the discovery and molecular mechanism of this compound. This compound was in the AstraZeneca/NCATS repurposing list from 2012.
iupac name: 4-[(2R)-4-tert-butylpiperazine-2-carbonyl]-N-(4-chloro-3-fluorophenyl)piperazine-1-carboxamide
synonym: AZD 2423
synonym: AZD-2423
approved: f
ligand name: AZD2423
type: SyntheticOrganicLigand

momelotinib
in ch i key: ZVHNDZWQTBEVRY-UHFFFAOYSA-N
in ch i: InChI=1S/C23H22N6O2/c24-10-12-25-22(30)18-3-1-17(2-4-18)21-9-11-26-23(28-21)27-19-5-7-20(8-6-19)29-13-15-31-16-14-29/h1-9,11H,12-16H2,(H,25,30)(H,26,27,28)
comment: Momelotinib (a.k.a. CYT387 and GS0387) is an investigational, oral, ATP-competitive Janus kinase inhibitor <Reference id=25893/>. Momelotinib also inhibits the bone morphogenetic protein kinase ACVR1 (activin A receptor type 1, ALK2), a mechanism that improves iron homeostasis and erythropoiesis via down-regulation of hepcidin <Reference id=43807/>, and which may provide benefit in anaemia in myelofibrosis <Reference id=43806/>.
iupac name: N-(cyanomethyl)-4-(2-((4-morpholinophenyl)amino)pyrimidin-4-yl)benzamide
xref: CHEMBL1078178
synonym: CYT-387
synonym: CYT387
synonym: GS-0387
synonym: GS0387
approved: f
ligand name: momelotinib
type: SyntheticOrganicLigand

AZD7268
in ch i key: ZJKUETLEJYCOBO-UHFFFAOYSA-N
in ch i: InChI=1S/C29H30N4O2S/c1-32(16-17-34)29(35)24-9-7-21(8-10-24)27(26-6-2-4-23-5-3-13-30-28(23)26)22-11-14-33(15-12-22)18-25-19-36-20-31-25/h2-10,13,19-20,34H,11-12,14-18H2,1H3
comment: AZD7268 is a potent, selective and reversible CNS‐penetrating and orally bioavailable δ-opioid receptor agonist. This compound was in the AstraZeneca/MRC repurposing list from 2011.
iupac name: N-(2-hydroxyethyl)-N-methyl-4-[quinolin-8-yl-[1-(1,3-thiazol-4-ylmethyl)piperidin-4-ylidene]methyl]benzamide
xref: CHEMBL1946618
synonym: AZ12488024
synonym: AZD 7268
synonym: AZD-7268
synonym: AZ 12488024
synonym: AZ-12488024
approved: f
ligand name: AZD7268
type: SyntheticOrganicLigand

AZD6605
in ch i key: SBVAXUGOISPYPX-QGZVFWFLSA-N
comment: AZD6605 is a potent, reversible inhibitor of matrix metalloproteinases MMP13 (Collagenase 3), MMP2, MMP9 and MMP12. The discovery of this compound is described in <Reference id=26016/>, where it is compound 3m. This compound was in the AstraZeneca/MRC repurposing list from 2011.
iupac name: (5S)-5-methyl-5-[[4-[4-(1,1,2,2-tetrafluoroethoxy)phenoxy]piperidin-1-yl]sulfonylmethyl]imidazolidine-2,4-dione
xref: CHEMBL2409707
synonym: AZ11920155
synonym: AZD 6605
synonym: AZD-6605
synonym: AZ 11920155
synonym: AZ-11920155
approved: f
ligand name: AZD6605
type: SyntheticOrganicLigand

AZD6088
in ch i key: IVJDEIANCSDDAO-ROUUACIJSA-N
in ch i: InChI=1S/C21H36N4O3/c1-3-28-20(27)23-14-10-21(2,11-15-23)24-12-8-16(9-13-24)25-18-7-5-4-6-17(18)22-19(25)26/h16-18H,3-15H2,1-2H3,(H,22,26)/t17-,18-/m0/s1
comment: The structure of AZD6088 is shown in <Reference id=26014/>. The compound is a potent and selective, orally bioavailable partial agonist of the M1 muscarinic receptor. This compound was in the AstraZeneca/MRC repurposing list from 2011
iupac name: propan-2-yl 4-[4-[(3aS,7aS)-2-oxo-3a,4,5,6,7,7a-hexahydro-3H-benzimidazol-1-yl]piperidin-1-yl]-4-methylpiperidine-1-carboxylate
synonym: AZ12677524
synonym: AZD 6088
synonym: AZD-6088
synonym: AZ 12677524
synonym: AZ-12677524
approved: f
ligand name: AZD6088
type: SyntheticOrganicLigand

AZD4619
in ch i key: CIHMPKKTGUOBBS-UHFFFAOYSA-N
in ch i: InChI=1S/C27H30O6S2/c1-20-3-5-22(6-4-20)16-18-34-26(27(28)29)19-23-9-7-21(8-10-23)15-17-32-24-11-13-25(14-12-24)33-35(2,30)31/h3-14,26H,15-19H2,1-2H3,(H,28,29)
comment: AZD4619 is a potent, selective and reversible orally bioavailable PPARα receptor agonist. This compound was in the AstraZeneca/MRC repurposing list from 2011
iupac name: 2-[2-(4-methylphenyl)ethylsulfanyl]-3-[4-[2-(4-methylsulfonyloxyphenoxy)ethyl]phenyl]propanoic acid
synonym: AZ11942571
synonym: AZD 4619
synonym: AZD-4619
approved: f
ligand name: AZD4619
type: SyntheticOrganicLigand

AZD1386
in ch i key: DXDVSYALLVVBOV-UHFFFAOYSA-N
comment: AZD1386 is an orally available antagonist of the transient receptor potential channel TRPV1. It acts as a competitive antagonist at the channel's capsaicin binding site . This compound was in the AstraZeneca/MRC repurposing list from 2011
synonym: KB-270807
synonym: AZ12457709
synonym: AZD-1386
synonym: AZD 1386
approved: f
ligand name: AZD1386
type: SyntheticOrganicLigand

AZD1080
isomeric SMILES: N#Cc1ccc2c(c1)/C(=c/1/ccc(c[nH]1)CN1CCOCC1)/C(=O)N2
in ch i key: JULOXTBHCHEFBE-ISLYRVAYSA-N
in ch i: InChI=1S/C19H18N4O2/c20-10-13-1-3-16-15(9-13)18(19(24)22-16)17-4-2-14(11-21-17)12-23-5-7-25-8-6-23/h1-4,9,11,21H,5-8,12H2,(H,22,24)/b18-17+
comment: AZD1080 is a selective, orally active, brain permeable GSK3 inhibitor, investigated in Phase I clinical trial for Alzheimer's disease. Development was subsequently discontinued. This compound was in the AstraZeneca/MRC repurposing list from 2011
iupac name: (3E)-3-[5-(morpholin-4-ylmethyl)-1H-pyridin-2-ylidene]-2-oxo-1H-indole-5-carbonitrile
synonym: KB-160506
synonym: AZD 1080
synonym: AZD-1080
approved: f
ligand name: AZD1080
type: SyntheticOrganicLigand

PH-797804
in ch i key: KCAJXIDMCNPGHZ-UHFFFAOYSA-N
comment: PH-797804 is a diarylpyridinone inhibitor of p38 mitogen-activated protein (MAP) kinase <Reference id=26007/>.
iupac name: 3-[3-bromo-4-[(2,4-difluorophenyl)methoxy]-6-methyl-2-oxopyridin-1-yl]-N,4-dimethylbenzamide
xref: CHEMBL1088751
approved: f
ligand name: PH-797804
type: SyntheticOrganicLigand

talmapimod
in ch i key: ZMELOYOKMZBMRB-DLBZAZTESA-N
comment: Talmapimod is an orally bioavailable, investigational small-molecule p38 mitogen-activated protein kinase (MAPK) inhibitor with potential immunomodulating, anti-inflammatory, and antineoplastic activities.
iupac name: 2-[6-chloro-5-[(2R,5S)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazine-1-carbonyl]-1-methylindol-3-yl]-N,N-dimethyl-2-oxoacetamide
xref: CHEMBL514201
synonym: SCIO-469
synonym: SCIO 469 hydrochloride
approved: f
ligand name: talmapimod
type: SyntheticOrganicLigand

orantinib
isomeric SMILES: OC(=O)CCc1c(C)[nH]c(c1C)/C=C/1/C(=O)Nc2c1cccc2
in ch i key: NHFDRBXTEDBWCZ-ZROIWOOFSA-N
in ch i: InChI=1S/C18H18N2O3/c1-10-12(7-8-17(21)22)11(2)19-16(10)9-14-13-5-3-4-6-15(13)20-18(14)23/h3-6,9,19H,7-8H2,1-2H3,(H,20,23)(H,21,22)/b14-9-
comment: Orantinib is a multi-kinase inhibitor.
iupac name: 3-[2,4-dimethyl-5-[(Z)-(2-oxo-1H-indol-3-ylidene)methyl]-1H-pyrrol-3-yl]propanoic acid
xref: CHEMBL274654
synonym: TSU-68
synonym: SU-6668
approved: f
ligand name: orantinib
type: SyntheticOrganicLigand

dilmapimod
in ch i key: ORVNHOYNEHYKJG-UHFFFAOYSA-N
in ch i: InChI=1S/C23H19F3N4O3/c1-12-9-13(24)5-6-15(12)20-16-7-8-19(33)30(21-17(25)3-2-4-18(21)26)22(16)29-23(28-20)27-14(10-31)11-32/h2-9,14,31-32H,10-11H2,1H3,(H,27,28,29)
comment: This is Example 64 in patent EP1333833 <Reference id=26004/>.
iupac name: 8-(2,6-difluorophenyl)-2-(1,3-dihydroxypropan-2-ylamino)-4-(4-fluoro-2-methylphenyl)pyrido[6,5-d]pyrimidin-7-one
xref: CHEMBL2103838
synonym: SB-681323
approved: f
ligand name: dilmapimod
type: SyntheticOrganicLigand

radotinib
in ch i key: DUPWHXBITIZIKZ-UHFFFAOYSA-N
in ch i: InChI=1S/C27H21F3N8O/c1-16-3-4-18(9-23(16)37-26-33-6-5-22(36-26)24-13-31-7-8-32-24)25(39)35-20-10-19(27(28,29)30)11-21(12-20)38-14-17(2)34-15-38/h3-15H,1-2H3,(H,35,39)(H,33,36,37)
comment: This drug is approved only in South Korea, for the treatment of chronic myeloid leukemia (CML), where its trade name is Supect. It is Example 5 in patent US7501424 <Reference id=26002/>. The marketed formulation contains the hydrochloride salt..
iupac name: 4-methyl-N-[3-(4-methylimidazol-1-yl)-5-(trifluoromethyl)phenyl]-3-[(4-pyrazin-2-ylpyrimidin-2-yl)amino]benzamide
synonym: Supect®
synonym: IY-5511
synonym: KB-146009
synonym: IY5511
synonym: IY5511HCl
approved: t
ligand name: radotinib
type: SyntheticOrganicLigand

OTS964
in ch i key: XCFRUAOZMVFDPQ-AWEZNQCLSA-N
in ch i: InChI=1S/C23H24N2O2S/c1-13-11-18(26)19(16-7-5-15(6-8-16)14(2)12-25(3)4)20-17-9-10-28-22(17)23(27)24-21(13)20/h5-11,14,26H,12H2,1-4H3,(H,24,27)/t14-/m0/s1
comment: OTS964 is a potent and selective inhibitor of the PDZ binding kinase, PBK (aka TOPK) <Reference id=25995/>. The compound is undergoing pre-clinical assessment.
iupac name: 9-{4-[(2R)-1-(dimethylamino)propan-2-yl]phenyl}-8-hydroxy-6-methyl-4H,5H-thieno[2,3-c]quinolin-4-one
approved: f
ligand name: OTS964
type: SyntheticOrganicLigand

RXP470.1
in ch i key: PTUCPHGSAFOJAU-MGONOCMRSA-N
comment: RXP470.1 is a potent and selective MMP-12 inhibitor (Ki 0.24 nM) and 3D structure 4GQL <Reference id=26025/>. In 2011 it was reported to reduce atherosclerotic plaque development in apolipoprotein E-knockout mice <Reference id=26024/>. A 2014 papert used RXP470.1 to indicate that inhibiting extracellular MMP-12 could be a new avenue for antiviral treatments <Reference id=26023/>. There are multiple stereoisomers in PubChem but the structure chosen connects the paper with the PDB structure and the assay data
iupac name: 4S)-5-amino-4-[[(2S)-2-[[(2S)-2-[[(4-bromophenyl)-hydroxyphosphoryl]methyl]-3-[3-[4-(3-chlorophenyl)phenyl]-1,2-oxazol-5-yl]propanoyl]amino]-4-carboxybutanoyl]amino]-5-oxopentanoic acid
xref: CHEMBL507420
approved: f
ligand name: RXP470.1
type: SyntheticOrganicLigand

compound 3 [PMID: 25408830]
in ch i key: LTUGYAOMCKNTGG-UHFFFAOYSA-N
in ch i: InChI=1S/C22H26N4O3/c1-24-18-13-16(23-21(27)15-9-5-6-10-20(15)29-3)17(26-11-7-4-8-12-26)14-19(18)25(2)22(24)28/h5-6,9-10,13-14H,4,7-8,11-12H2,1-3H3,(H,23,27)
comment: The discovery and activity of this compound is described in Demont et al (2014) <Reference id=25994/>.
iupac name: N-(1,3-dimethyl-2-oxo-6-piperidin-1-ylbenzimidazol-5-yl)-2-methoxybenzamide
xref: CHEMBL1522313
approved: f
ligand name: compound 3 [PMID: 25408830]
type: SyntheticOrganicLigand

compound 2 [PMID: 25408830]
in ch i key: HVGVNYJRZJHYBS-UHFFFAOYSA-N
in ch i: InChI=1S/C17H19N3O3S/c1-11-5-8-16(12(2)9-11)24(22,23)18-13-6-7-14-15(10-13)20(4)17(21)19(14)3/h5-10,18H,1-4H3
comment: The discovery and activity of this compound is described in Demont et al (2014) <Reference id=25994/>.
iupac name: N-(1,3-dimethyl-2-oxobenzimidazol-5-yl)-2,4-dimethylbenzenesulfonamide
xref: CHEMBL1444120
approved: f
ligand name: compound 2 [PMID: 25408830]
type: SyntheticOrganicLigand

ET bromodomain inhibitor
in ch i key: WGMDCNPABCIZCD-UTKZUKDTSA-N
in ch i: InChI=1S/C23H23ClN4O3/c1-5-17(23(29)31-4)21-22-27-26-13(2)28(22)19-11-10-16(30-3)12-18(19)20(25-21)14-6-8-15(24)9-7-14/h6-12,17,21H,5H2,1-4H3/t17-,21+/m1/s1
comment: The chemical structure shown here is the (1S-2R) isomer of the compound ET, this represented the minor product of the synthesis <Reference id=25993/>, with the major component being the (1S-2S) isomer. Data from the manuscript was produced using the former isomer, simply called ET in the text.
iupac name: methyl (2R)-2-[(4S)-6-(4-chlorophenyl)-8-methoxy-1-methyl-4H-[1,2,4]triazolo[4,3-a][1,4]benzodiazepin-4-yl]butanoate
approved: f
ligand name: ET bromodomain inhibitor
type: SyntheticOrganicLigand

ME bromodomain inhibitor
in ch i key: FENXDXHDXYVGRJ-BLVKFPJESA-N
in ch i: InChI=1S/C22H21ClN4O3/c1-12(22(28)30-4)19-21-26-25-13(2)27(21)18-10-9-16(29-3)11-17(18)20(24-19)14-5-7-15(23)8-6-14/h5-12,19H,1-4H3/t12-,19+/m1/s1
comment: The chemical structure shown here is the (1S-2R) isomer of the compound ME, this represented the minor product of the synthesis <Reference id=25993/>, with the major component being the (1S-2S) isomer. Data from the manuscript was produced using the former isomer, simply called ME in the text.
iupac name: methyl (2R)-2-[(4S)-6-(4-chlorophenyl)-8-methoxy-1-methyl-4H-[1,2,4]triazolo[4,3-a][1,4]benzodiazepin-4-yl]propanoate
approved: f
ligand name: ME bromodomain inhibitor
type: SyntheticOrganicLigand

purvalanol B
in ch i key: ZKDXRFMOHZVXSG-HNNXBMFYSA-N
in ch i: InChI=1S/C20H25ClN6O3/c1-10(2)15(8-28)24-20-25-17(16-18(26-20)27(9-22-16)11(3)4)23-12-5-6-13(19(29)30)14(21)7-12/h5-7,9-11,15,28H,8H2,1-4H3,(H,29,30)(H2,23,24,25,26)/t15-/m0/s1
comment: Purvalanol B is a cyclin-dependent kinase (CDK) inhibitor <Reference id=25659/>.
iupac name: 2-chloro-4-[[2-[[(2R)-1-hydroxy-3-methylbutan-2-yl]amino]-9-propan-2-ylpurin-6-yl]amino]benzoic acid
xref: CHEMBL23254
synonym: NG95
synonym: NG-95
approved: f
ligand name: purvalanol B
type: SyntheticOrganicLigand

AZ4800
in ch i key: RMRFSIAFQBYBSN-UHFFFAOYSA-N
in ch i: InChI=1S/C24H29N5O3/c1-16-12-29(15-25-16)22-8-7-17(11-23(22)30-2)26-24-27-20-9-10-31-13-19(20)21(28-24)14-32-18-5-3-4-6-18/h7-8,11-12,15,18H,3-6,9-10,13-14H2,1-2H3,(H,26,27,28)
comment: AZD4800 is one of several AstraZeneca gamma secretase modulators <Reference id=25940/>. It has recently been used for targeting amyloid β production in a mouse model of Alzheimer's disease (AD) in combination with the BACE1 inhibitor <Ligand id=7804/> <Reference id=25937/>.
iupac name: 4-(cyclopentyloxymethyl)-N-[3-methoxy-4-(4-methylimidazol-1-yl)phenyl]-7,8-dihydro-5H-pyrano[4,3-d]pyrimidin-2-amine
xref: CHEMBL2151176
synonym: AZ 4800
synonym: AZ-4800
approved: f
ligand name: AZ4800
type: SyntheticOrganicLigand

AZ3971
in ch i key: BICGYFRWDDPYEI-VWLOTQADSA-N
in ch i: InChI=1S/C25H22N6O/c1-15-9-20(10-16(2)22(15)32-3)25(23-21(24(26)31-25)29-7-8-30-23)19-6-4-5-17(11-19)18-12-27-14-28-13-18/h4-14H,1-3H3,(H2,26,31)/t25-/m0/s1
comment: AZD3971 is an AstraZeneca BACE1 inhibitor. While not published in its own right so far, it has been reported for targeting amyloid beta production in a mouse model of Alzheimer's disease (AD) in combination with the gamma secretase modulator <Ligand id=7805/> <Reference id=25937/>.
iupac name: (5S)-5-(4-methoxy-3,5-dimethylphenyl)-5-(3-pyrimidin-5-ylphenyl)pyrrolo[3,4-b]pyrazin-7-amine
synonym: AZ 3971
synonym: AZ-3971
approved: f
ligand name: AZ3971
type: SyntheticOrganicLigand

compound 15 [PMID: 25313322]
canonical SMILES: CNc1nc(NCc2ccc(cc2Cl)Cl)cc(n1)c1ccccn1
isomeric SMILES: CNc1nc(NCc2ccc(cc2Cl)Cl)cc(n1)c1ccccn1
in ch i key: HOVRMCPKCWLHJS-UHFFFAOYSA-N
in ch i: InChI=1S/C17H15Cl2N5/c1-20-17-23-15(14-4-2-3-7-21-14)9-16(24-17)22-10-11-5-6-12(18)8-13(11)19/h2-9H,10H2,1H3,(H2,20,22,23,24)
iupac name: 4-N-[(2,4-dichlorophenyl)methyl]-2-N-methyl-6-pyridin-2-ylpyrimidine-2,4-diamine
approved: f
ligand name: compound 15 [PMID: 25313322]
type: SyntheticOrganicLigand

compound 1 [PMID: 24900608]
in ch i key: UGDJVSURAKMIPU-UHFFFAOYSA-N
in ch i: InChI=1S/C18H17ClN6/c19-15-2-4-18-22-16(13-25(18)11-15)12-23-5-7-24(8-6-23)17-3-1-14(9-20)10-21-17/h1-4,10-11,13H,5-8,12H2
iupac name: 6-[4-[(6-chloroimidazo[1,2-a]pyridin-2-yl)methyl]piperazin-1-yl]pyridine-3-carbonitrile
xref: CHEMBL3092413
approved: f
ligand name: compound 1 [PMID: 24900608]
type: SyntheticOrganicLigand

compound 1a [PMID: 24900311]
in ch i key: IFQNPGNCFXITTG-UHFFFAOYSA-N
in ch i: InChI=1S/C20H19N3O4/c1-26-17-10-15(11-18(12-17)27-2)19(24)22-23-20(25)21-16-8-7-13-5-3-4-6-14(13)9-16/h3-12H,1-2H3,(H,22,24)(H2,21,23,25)
comment: Compound 1a is a surrogate agonist for GPR139, identified in a screening study <Reference id=25906/>.
iupac name: 1-[(3,5-dimethoxybenzoyl)amino]-3-naphthalen-2-ylurea
approved: f
ligand name: compound 1a [PMID: 24900311]
type: SyntheticOrganicLigand

compound 2 [PMID: 24793972]
in ch i key: OBGKRTYDTRUMGO-RFNYNIMXSA-N
in ch i: InChI=1S/C30H37N3O/c1-4-8-22-10-12-23(13-11-22)24-14-16-25(17-15-24)33(20-28(31)21(3)5-2)30(34)27-19-26(27)29-9-6-7-18-32-29/h6-7,9-18,21,26-28H,4-5,8,19-20,31H2,1-3H3/t21-,26+,27+,28+/m0/s1
iupac name: (1R,2R)-N-[(2S,3S)-2-amino-3-methylpentyl]-N-[4-(4-propylphenyl)phenyl]-2-pyridin-2-ylcyclopropane-1-carboxamide
synonym: (1R,2R)-2-PCCA
approved: f
ligand name: compound 2 [PMID: 24793972]
type: SyntheticOrganicLigand

galunisertib
in ch i key: IVRXNBXKWIJUQB-UHFFFAOYSA-N
in ch i: InChI=1S/C22H19N5O/c1-13-4-2-5-18(25-13)21-20(19-6-3-11-27(19)26-21)15-9-10-24-17-8-7-14(22(23)28)12-16(15)17/h2,4-5,7-10,12H,3,6,11H2,1H3,(H2,23,28)
comment: Galunisertib is a first-in-class investigational inhibitor of the receptor tyrosine kinase, growth factor-β receptor type I (TGFβRI) <Reference id=35971/><Reference id=35972/>. It is being evaluated as a novel anticancer agent.
iupac name: 4-[2-(6-methylpyridin-2-yl)-5,6-dihydro-4H-pyrrolo[2,1-e]pyrazol-3-yl]quinoline-6-carboxamide
xref: CHEMBL2364611
synonym: LY2157299
synonym: LY-2157299
synonym: inhibitor 15d [PMID: 18314943]
approved: f
ligand name: galunisertib
type: SyntheticOrganicLigand

fostamatinib
in ch i key: GKDRMWXFWHEQQT-UHFFFAOYSA-N
in ch i: InChI=1S/C23H26FN6O9P/c1-23(2)21(31)30(11-38-40(32,33)34)20-14(39-23)6-7-17(28-20)27-19-13(24)10-25-22(29-19)26-12-8-15(35-3)18(37-5)16(9-12)36-4/h6-10H,11H2,1-5H3,(H2,32,33,34)(H2,25,26,27,28,29)
comment: Fostamatinib is a spleen tyrosine kinase (Syk) inhibitor prodrug. Fostamatinib is administered orally in disodium salt preparations (e.g. PubChem CID 25008120 and fostamatinib disodium hexahydrate CID 24828759). It is rapidly converted to <Ligand id=5706/> by alkaline phosphatases in intestinal enterocytes <Reference id=25900/>. Although development in rheumatoid arthritis was discontinued in 2013 due to a lack of observed efficacy, development continued in patients with chronic and persistent immune thrombocytopenia (ITP).
iupac name: [6-[[5-fluoro-2-[(3,4,5-trimethoxyphenyl)amino]pyrimidin-4-yl]amino]-2,2-dimethyl-3-oxopyrido[2,3-e][1,4]oxazin-4-yl]methyl dihydrogen phosphate
xref: CHEMBL2103830
synonym: R-788
synonym: R 788
synonym: R7935788
synonym: Tavalisse®
synonym: Tavlesse®
approved: t
ligand name: fostamatinib
type: SyntheticOrganicLigand

taselisib
in ch i key: BEUQXVWXFDOSAQ-UHFFFAOYSA-N
in ch i: InChI=1S/C24H28N8O2/c1-14(2)32-22(27-15(3)29-32)19-13-30-8-9-34-20-10-16(6-7-18(20)21(30)28-19)17-11-26-31(12-17)24(4,5)23(25)33/h6-7,10-14H,8-9H2,1-5H3,(H2,25,33)
comment: Taselisib is a potent and orally bioavailable kinase inhibitor which inhibits the PI3Kα, γ and δ isoforms but not the β isoform. It is compound 11l in <Reference id=25897/>.
iupac name: 2-(4-(2-(1-isopropyl-3-methyl-1H-1,2,4-triazol-5-yl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepin-9-yl)-1H-pyrazol-1-yl)-2-methylpropanamide
xref: CHEMBL2387080
synonym: GDC-0032
synonym: GDC0032
approved: f
ligand name: taselisib
type: SyntheticOrganicLigand

pacritinib
in ch i key: HWXVIOGONBBTBY-ONEGZZNKSA-N
in ch i: InChI=1S/C28H32N4O3/c1-2-13-32(12-1)14-17-35-27-9-8-25-19-24(27)21-34-16-4-3-15-33-20-22-6-5-7-23(18-22)26-10-11-29-28(30-25)31-26/h3-11,18-19H,1-2,12-17,20-21H2,(H,29,30,31)/b4-3+
comment: Pacritinib is an orally bioavailable and somewhat selective inhibitor of Janus kinase 2 (JAK2) and the JAK2 gain-of-function mutant JAK2V617F <Reference id=25896/>. At clinically relevant concentrations, pacritinib does not inhibit JAK1. It also has some inhibitory activity against FMS-like tyrosine kinase 3 (FLT3).
iupac name: 11-(2-pyrrolidin-1-yl-ethoxy)-14,19-dioxa-5,7,26-triaza-tetracyclo[19.3.1.1(2,6).1(8,12)]heptacosa-1(25),2(26),3,5,8,10,12(27),16,21,23-decaene
xref: CHEMBL2035187
synonym: SB1518
synonym: SB-1518
synonym: Vonjo®
approved: t
ligand name: pacritinib
type: SyntheticOrganicLigand

baricitinib
in ch i key: XUZMWHLSFXCVMG-UHFFFAOYSA-N
in ch i: InChI=1S/C16H17N7O2S/c1-2-26(24,25)22-9-16(10-22,4-5-17)23-8-12(7-21-23)14-13-3-6-18-15(13)20-11-19-14/h3,6-8,11H,2,4,9-10H2,1H3,(H,18,19,20)
comment: Baricitinib is a JAK1 and 2 selective inhibitor. The compound is orally bioavailable. SARS-CoV-2 and COVID-19: The powerful anti-inflammatory activity of baricitinib (and potentially other approved JAK inhibitors such as <Ligand id=5716/>, and <Ligand id=5688/>) was suggested as potential therapeutic option to combat the immunopathological effects of SARS-CoV-2 infection in patients with severe COVID-19. A number of small-medium sized clinical studies have examined the effect of short-term baricitinib (or other JAK inhibitors) treatment in hospitalised patients with confirmed COVID-19. Such short term use of this drug during the course of SARS-CoV-2 infection (7-14 days) is not anticipated to cause serious side-effects. In March 2022, data reported from the largest of the baricitinib studies (part of the University of Oxford-led RECOVERY trial) indicated that it provided clinical benefit in hospitalised COVID-19 patients, including in those already receiving other standard care immunomodulatory treatments (e.g. <Ligand id=2768/>, <Ligand id=6881/>) or the antiviral drug <Ligand id=10715/>. This made baricitinib the 4th effective COVID-19 therapy to be identified by the RECOVERY trial. Through the application of proprietary artificial intelligence (AI) algorithms baricitinib was predicted to possess antiviral activity in addition to its known anti-inflammatory efficacy <Reference id=38933/><Reference id=38934/><Reference id=38937/>. Antiviral activity is predicted to arise from inhibition of the numb-associated kinase (NAK) AAK1 which is an important regulator of clathrin-mediated endocytosis. Inhibition of AAK1 would likely reduce the ability of viruses to infect lung cells, and is being proposed as a pharmacological mechanism that warrants further investigation as a treatment for SARS-CoV-2 infection.
iupac name: 2-(3-(4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl)-1-(ethylsulfonyl)azetidin-3-yl)acetonitrile
xref: CHEMBL2105759
synonym: Olumiant®
synonym: INCB-028050
synonym: LY3009104
synonym: LY-3009104
synonym: INCB028050
approved: t
ligand name: baricitinib
type: SyntheticOrganicLigand

alisertib
in ch i key: ZLHFILGSQDJULK-UHFFFAOYSA-N
comment: Alisertib is a second generation, orally bioavailable and selective Aurora kinase A inhibitor.
iupac name: 4-[[9-chloro-7-(2-fluoro-6-methoxyphenyl)-5H-pyrimido[5,4-d][2]benzazepin-2-yl]amino]-2-methoxybenzoic acid
xref: CHEMBL483158
synonym: MLN-8237
approved: f
ligand name: alisertib
type: SyntheticOrganicLigand

florbetaben
canonical SMILES: FCCOCCOCCOc1ccc(cc1)C=Cc1ccc(cc1)NC
in ch i key: NCWZOASIUQVOFA-FWZJPQCDSA-N
in ch i: InChI=1S/C21H26FNO3/c1-23-20-8-4-18(5-9-20)2-3-19-6-10-21(11-7-19)26-17-16-25-15-14-24-13-12-22/h2-11,23H,12-17H2,1H3/b3-2+/i22-1
comment: Florbetaben F18 is the third PET (positron-emission tomography) reagent approved to identify amyloid-β (Aβ) as a diagnostic biomarker in the brains of patients with Alzheimer's disease (AD) <Reference id=25790/>. <Ligand id=7342/> and <Ligand id=7344/> are the two other PET reagents approved for Aβ detection. These diagnostic tools allow direct and non-invasive in vivo visualisation and quantification of Aβ.
synonym: AV-1
synonym: Neuraceq®
synonym: [18F]BAY 94-9172
synonym: BAY 94-9172
approved: t
ligand name: florbetaben
type: SyntheticOrganicLigand

lanabecestat
in ch i key: WKDNQONLGXOZRG-BOPKNSRXSA-N
in ch i: InChI=1S/C26H28N4O/c1-4-5-18-12-21(16-28-15-18)19-6-7-20-14-25(10-8-22(31-3)9-11-25)26(23(20)13-19)29-17(2)24(27)30-26/h6-7,12-13,15-16,22H,8-11,14H2,1-3H3,(H2,27,30)/t22?,25?,26-/m0/s1
comment: Lanabecestat (AZD3293) is an oral, potent and selective small molecule inhibitor of BACE1 being developed by AstraZeneca and Eli Lilly <Reference id=33426/> . It is now proceeding to Phase III trials <Reference id=33425/>. Note our initial chemical assignment was based on the crystallisation data in US20140031379 <Reference id=27249/> but the name is now attached to two CIDs, the one designated in this entry with correct stereoisomer and the flat form as PubChem CID 57404290
iupac name: 4-methoxy-5'-methyl-6'-(5-(prop-1-yn-1-yl)pyridin-3-yl)-3'H-dispiro(cyclohexane-1,2'-inden-1',2'-imidazol)-4'-amine
synonym: LY3314814
synonym: AZD 3293
synonym: AZD-3293
approved: f
ligand name: lanabecestat
type: SyntheticOrganicLigand

trans-JB253
in ch i key: FCHDFDWESRUUDK-UHFFFAOYSA-N
in ch i: InChI=1S/C23H31N5O3S/c1-3-28(4-2)21-14-10-19(11-15-21)25-26-20-12-16-22(17-13-20)32(30,31)27-23(29)24-18-8-6-5-7-9-18/h10-18H,3-9H2,1-2H3,(H2,24,27,29)
comment: trans-JB253 is the inactive photoisomer of <Ligand id=7787/> <Reference id=25887/>.
iupac name: 1-cyclohexyl-3-{4-[(E)-2-[4-(diethylamino)phenyl]diazen-1-yl]benzenesulfonyl}urea
approved: f
ligand name: trans-JB253
type: SyntheticOrganicLigand

cis-JB253
isomeric SMILES: CCN(c1ccc(cc1)/N=N/c1ccc(cc1)S(=O)(=O)NC(=O)NC1CCCCC1)CC
in ch i key: FCHDFDWESRUUDK-QPLCGJKRSA-N
in ch i: InChI=1S/C23H31N5O3S/c1-3-28(4-2)21-14-10-19(11-15-21)25-26-20-12-16-22(17-13-20)32(30,31)27-23(29)24-18-8-6-5-7-9-18/h10-18H,3-9H2,1-2H3,(H2,24,27,29)/b26-25-
comment: cis-JB253 is described in <Reference id=25887/>. The structure is based upon that of the diabetes sulfonylurea drug <Ligand id=6820/>. This compound is formed from <Ligand id=7788/> upon photoisomerization using blue light. This isomerization process is reversible. The molecule is active in the cis-state, increasing insulin production from pancreatic B-cells in vitro. It is postulated that this type of photoswitchable compound could in the future, allow better control of blood glucose in diabetic patients <Reference id=25887/>. Note that the PubChem CID we link to does not specify the cis-trans state of the compound.
iupac name: 1-cyclohexyl-3-{4-[(Z)-2-[4-(diethylamino)phenyl]diazen-1-yl]benzenesulfonyl}urea
approved: f
ligand name: cis-JB253
type: SyntheticOrganicLigand

CCG-50014
canonical SMILES: Cc1ccc(cc1)n1sc(=O)n(c1=O)Cc1ccc(cc1)F
isomeric SMILES: Cc1ccc(cc1)n1sc(=O)n(c1=O)Cc1ccc(cc1)F
in ch i key: QUIIIYITNGOFEI-UHFFFAOYSA-N
in ch i: InChI=1S/C16H13FN2O2S/c1-11-2-8-14(9-3-11)19-15(20)18(16(21)22-19)10-12-4-6-13(17)7-5-12/h2-9H,10H2,1H3
comment: CCG-50014 is a potent small molecule inhibitor of regulator of G-protein signaling protein 4 (RGS4) <Reference id=25881/>.
iupac name: 4-[(4-fluorophenyl)methyl]-2-(4-methylphenyl)-1,2,4-thiadiazolidine-3,5-dione
xref: CHEMBL1917204
synonym: CCG 50014
synonym: compound 1a
synonym: CCG50014
approved: f
ligand name: CCG-50014
type: SyntheticOrganicLigand

UCM 454
canonical SMILES: CCC(=O)NCc1cc2c(n1Cc1ccc(cc1)Cl)cccc2OC
isomeric SMILES: CCC(=O)NCc1cc2c(n1Cc1ccc(cc1)Cl)cccc2OC
in ch i key: XXXKKZBZKUDKMA-UHFFFAOYSA-N
in ch i: InChI=1S/C20H21ClN2O2/c1-3-20(24)22-12-16-11-17-18(5-4-6-19(17)25-2)23(16)13-14-7-9-15(21)10-8-14/h4-11H,3,12-13H2,1-2H3,(H,22,24)
iupac name: N-[[1-[(4-chlorophenyl)methyl]-4-methoxyindol-2-yl]methyl]propanamide
xref: CHEMBL33185
synonym: UCM-454
synonym: UCM454
approved: f
ligand name: UCM 454
type: SyntheticOrganicLigand

2-(indolin-1yl)-melatonin
in ch i key: WPMBIMXWTHXWHN-UHFFFAOYSA-N
in ch i: InChI=1S/C22H25N3O2/c1-15(26)23-11-9-18-19-13-17(27-2)7-8-20(19)24-21(18)14-25-12-10-16-5-3-4-6-22(16)25/h3-8,13,24H,9-12,14H2,1-2H3,(H,23,26)
iupac name: N-[2-[2-(2,3-dihydroindol-1-ylmethyl)-5-methoxy-1H-indol-3-yl]ethyl]acetamide
xref: CHEMBL514415
approved: f
ligand name: 2-(indolin-1yl)-melatonin
type: SyntheticOrganicLigand

CIFEA
canonical SMILES: CC(=O)NCCC1=C(CC2CCCCC2)Cc2c1c1CCOc1cc2
isomeric SMILES: CC(=O)NCCC1=C(CC2CCCCC2)Cc2c1c1CCOc1cc2
in ch i key: MMMAALHYEKMNHU-UHFFFAOYSA-N
in ch i: InChI=1S/C22H29NO2/c1-15(24)23-11-9-19-18(13-16-5-3-2-4-6-16)14-17-7-8-21-20(22(17)19)10-12-25-21/h7-8,16H,2-6,9-14H2,1H3,(H,23,24)
iupac name: N-[2-[7-(cyclohexylmethyl)-2,6-dihydro-1H-cyclopenta[e][1]benzofuran-8-yl]ethyl]acetamide
xref: CHEMBL1774519
synonym: cyclohexylmethyl-indenofurane-ethylacetamide
approved: f
ligand name: CIFEA
type: SyntheticOrganicLigand

[125I]S70254
in ch i key: ZYVDSJZCXRMXGR-FOKFMTIASA-N
in ch i: InChI=1S/C22H20IN3O2/c1-28-20-10-9-18-22(26-20)17(11-12-24-19(27)13-23)21(25-18)16-8-4-6-14-5-2-3-7-15(14)16/h2-10,25H,11-13H2,1H3,(H,24,27)/i23-2
approved: f
ligand name: [125I]S70254
type: SyntheticOrganicLigand

CBOBNEA
in ch i key: VTMXSWVEWDJSKG-UHFFFAOYSA-N
in ch i: InChI=1S/C31H31NO5/c1-22(33)32-18-17-26-6-4-5-25-13-16-29(21-30(25)26)37-20-3-2-19-36-28-14-11-24(12-15-28)23-7-9-27(10-8-23)31(34)35/h4-16,21H,2-3,17-20H2,1H3,(H,32,33)(H,34,35)
iupac name: 4-[4-[4-[8-(2-acetamidoethyl)naphthalen-2-yl]oxybutoxy]phenyl]benzoic acid
xref: CHEMBL1094546
synonym: carboxybiphenyloxy-butoxy-naphthalen-ethylacetamide
approved: f
ligand name: CBOBNEA
type: SyntheticOrganicLigand

UCM 793
canonical SMILES: COc1cccc(c1)N(CCNC(=O)C)C
isomeric SMILES: COc1cccc(c1)N(CCNC(=O)C)C
in ch i key: FAWOXVGCBAVSFR-UHFFFAOYSA-N
in ch i: InChI=1S/C12H18N2O2/c1-10(15)13-7-8-14(2)11-5-4-6-12(9-11)16-3/h4-6,9H,7-8H2,1-3H3,(H,13,15)
iupac name: N-[2-[(3-methoxyphenyl)-methylamino]ethyl]acetamide
xref: CHEMBL237236
synonym: UCM-793
synonym: UCM793
approved: f
ligand name: UCM 793
type: SyntheticOrganicLigand

difluoroagomelatine
canonical SMILES: COc1ccc2c(c1)c(CCNC(=O)C(F)F)ccc2
isomeric SMILES: COc1ccc2c(c1)c(CCNC(=O)C(F)F)ccc2
in ch i key: UTLRQLQDJLNKNY-UHFFFAOYSA-N
in ch i: InChI=1S/C15H15F2NO2/c1-20-12-6-5-10-3-2-4-11(13(10)9-12)7-8-18-15(19)14(16)17/h2-6,9,14H,7-8H2,1H3,(H,18,19)
iupac name: 2,2-difluoro-N-[2-(7-methoxynaphthalen-1-yl)ethyl]acetamide
xref: CHEMBL1946221
approved: f
ligand name: difluoroagomelatine
type: SyntheticOrganicLigand

2-methoxy-α,β-didehydro-agomelatine
canonical SMILES: COc1ccc2c(c1C=CNC(=O)C)cc(cc2)OC
isomeric SMILES: COc1ccc2c(c1/C=C/NC(=O)C)cc(cc2)OC
in ch i key: HMYFXYOFPXZULT-CMDGGOBGSA-N
in ch i: InChI=1S/C16H17NO3/c1-11(18)17-9-8-14-15-10-13(19-2)6-4-12(15)5-7-16(14)20-3/h4-10H,1-3H3,(H,17,18)/b9-8+
iupac name: N-[(E)-2-(2,7-dimethoxynaphthalen-1-yl)ethenyl]acetamide
xref: CHEMBL2314259
approved: f
ligand name: 2-methoxy-α,β-didehydro-agomelatine
type: SyntheticOrganicLigand

EFPPEA
canonical SMILES: CCc1nn2c(c1CCNC(=O)C)c1CCOc1cc2
isomeric SMILES: CCc1nn2c(c1CCNC(=O)C)c1CCOc1cc2
in ch i key: IZDHETWMKYCGAU-UHFFFAOYSA-N
in ch i: InChI=1S/C15H19N3O2/c1-3-13-11(4-7-16-10(2)19)15-12-6-9-20-14(12)5-8-18(15)17-13/h5,8H,3-4,6-7,9H2,1-2H3,(H,16,19)
xref: CHEMBL1802025
synonym: ethyl-furo-pyrazolo-pyridine-ethyl-acetamide
synonym: N-[2-(2-Ethyl-8,9-dihydrofuro[3,2-c]pyrazolo[1,5-a]pyridin-1-yl)ethyl]acetamide
approved: f
ligand name: EFPPEA
type: SyntheticOrganicLigand

UCM 724
canonical SMILES: COc1ccc2c(c1)C(CNC(=O)N)Cc1c(C2)cccc1
isomeric SMILES: COc1ccc2c(c1)C(CNC(=O)N)Cc1c(C2)cccc1
in ch i key: DIXNMQKCFFPTKU-UHFFFAOYSA-N
in ch i: InChI=1S/C18H20N2O2/c1-22-16-7-6-14-8-12-4-2-3-5-13(12)9-15(17(14)10-16)11-20-18(19)21/h2-7,10,15H,8-9,11H2,1H3,(H3,19,20,21)
iupac name: (3-methoxy-6,11-dihydro-5H-dibenzo[2,1-b:1',3'-f][7]annulen-5-yl)methylurea
synonym: UCM-724
synonym: UCM724
approved: f
ligand name: UCM 724
type: SyntheticOrganicLigand

UCM 549
canonical SMILES: COc1ccc2c(c1)C(CNC(=O)C)Cc1c(C2)cccc1
isomeric SMILES: COc1ccc2c(c1)C(CNC(=O)C)Cc1c(C2)cccc1
in ch i key: PQZZGTZTKGECDT-UHFFFAOYSA-N
in ch i: InChI=1S/C19H21NO2/c1-13(21)20-12-17-10-15-6-4-3-5-14(15)9-16-7-8-18(22-2)11-19(16)17/h3-8,11,17H,9-10,12H2,1-2H3,(H,20,21)
xref: CHEMBL189449
synonym: UCM-549
synonym: UCM549
approved: f
ligand name: UCM 549
type: SyntheticOrganicLigand

[125I]DIV880
in ch i key: UIYQREMVBQNPNM-XXFZXMJFSA-N
in ch i: InChI=1S/C23H29IO6/c1-23(2,3)30-22(25)12-15-10-19(27-5)18(26-4)9-14(15)8-16-11-20(28-6)21(29-7)13-17(16)24/h9-11,13H,8,12H2,1-7H3/i24-2
approved: f
ligand name: [125I]DIV880
type: SyntheticOrganicLigand

[125I]SD6
canonical SMILES: COc1cc2c(CCNC(=O)CI)c[nH]c2cc1
isomeric SMILES: COc1cc2c(CCNC(=O)C[125I])c[nH]c2cc1
in ch i key: BCFPPJOYYKSYLA-XSBOKVBDSA-N
in ch i: InChI=1S/C13H15IN2O2/c1-18-10-2-3-12-11(6-10)9(8-16-12)4-5-15-13(17)7-14/h2-3,6,8,16H,4-5,7H2,1H3,(H,15,17)/i14-2
comment: [125I]-SD6 is a radio-labelled, non-selective melatonin receptor ligand.
approved: f
ligand name: [125I]SD6
type: SyntheticOrganicLigand

cilnidipine
canonical SMILES: COCCOC(=O)C1=C(C)NC(=C(C1c1cccc(c1)[N+](=O)[O-])C(=O)OCC=Cc1ccccc1)C
isomeric SMILES: COCCOC(=O)C1=C(C)NC(=C(C1c1cccc(c1)[N+](=O)[O-])C(=O)OC/C=C/c1ccccc1)C
in ch i key: KJEBULYHNRNJTE-DHZHZOJOSA-N
in ch i: InChI=1S/C27H28N2O7/c1-18-23(26(30)35-14-8-11-20-9-5-4-6-10-20)25(21-12-7-13-22(17-21)29(32)33)24(19(2)28-18)27(31)36-16-15-34-3/h4-13,17,25,28H,14-16H2,1-3H3/b11-8+
comment: Cilnidipine is a calcium channel blocking antihypertensive drug.
iupac name: O3-(2-methoxyethyl) O5-(3-phenylprop-2-enyl) 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate
xref: CHEMBL452076
synonym: FRC-8653
approved: t
ligand name: cilnidipine
type: SyntheticOrganicLigand

TROX-1
in ch i key: OABSWPUPIHULMQ-JOCHJYFZSA-N
in ch i: InChI=1S/C22H16ClFN6O/c1-22(8-13-9-25-11-26-10-13)16-6-14(15-2-4-18(24)17(23)7-15)3-5-19(16)30(20(22)31)21-27-12-28-29-21/h2-7,9-12H,8H2,1H3,(H,27,28,29)/t22-/m1/s1
comment: Note that this compound is also represented on PubChem by CID 25256198 which does not specifiy stereochemistry.
iupac name: (3R)-5-(3-chloro-4-fluorophenyl)-3-methyl-3-(pyrimidin-5-ylmethyl)-1-(1H-1,2,4-triazol-5-yl)indol-2-one
approved: f
ligand name: TROX-1
type: SyntheticOrganicLigand

NP118809
in ch i key: VCPMZDWBEWTGNW-UHFFFAOYSA-N
in ch i: InChI=1S/C32H32N2O/c35-31(25-30(26-13-5-1-6-14-26)27-15-7-2-8-16-27)33-21-23-34(24-22-33)32(28-17-9-3-10-18-28)29-19-11-4-12-20-29/h1-20,30,32H,21-25H2
iupac name: 1-[4-[di(phenyl)methyl]piperazin-1-yl]-3,3-di(phenyl)propan-1-one
xref: CHEMBL604710
synonym: NP-118809
synonym: NP 118809
approved: f
ligand name: NP118809
type: SyntheticOrganicLigand

RY796
in ch i key: LDXZFQWWXMRMAS-HNNXBMFYSA-N
in ch i: InChI=1S/C21H27N3O2/c1-14(2)20(25)23-17-11-12-19(24(4)5)18(13-17)21(26)22-15(3)16-9-7-6-8-10-16/h6-15H,1-5H3,(H,22,26)(H,23,25)/t15-/m0/s1
comment: RY796 is the S-enantiomer as reported in <Reference id=25622/>. It is a selective Kv2 channel inhibitor.
iupac name: 2-(dimethylamino)-5-(2-methylpropanoylamino)-N-[(1S)-1-phenylethyl]benzamide
xref: CHEMBL2324356
synonym: RY 796
synonym: RY-796
approved: f
ligand name: RY796
type: SyntheticOrganicLigand

compound 38 [PMID: 22123324]
in ch i key: LMNFAMWQPPUUNJ-AREMUKBSSA-N
in ch i: InChI=1S/C30H34N4O/c1-2-15-32-26-19-30(25-9-5-3-8-23(25)26)13-16-33(17-14-30)20-21-11-12-28-24(18-21)22-7-4-6-10-27(22)34(28)29(31)35/h3-12,18,26,32H,2,13-17,19-20H2,1H3,(H2,31,35)/t26-/m1/s1
comment: The synthesis of this MCH2 receptor antagonist is described in <Reference id=25604/>. The image drawn in this article is somewhat unclear as to the stereochemistry of the bond to the NH-acetyl side chain. We have drawn this as a R bond.
iupac name: 3-[[(1R)-1-(propylamino)spiro[1,2-dihydroindene-3,4'-piperidine]-1'-yl]methyl]carbazole-9-carboxamide
approved: f
ligand name: compound 38 [PMID: 22123324]
type: SyntheticOrganicLigand

pyrrolidine MCHR1 antagonist 1
in ch i key: OLINDOIRFAZHRH-GBXCKJPGSA-N
in ch i: InChI=1S/C26H33ClN2O4/c1-32-23-7-5-19(6-8-23)24-18-29(12-9-26(31)10-13-33-14-11-26)17-20(24)15-25(30)28-22-4-2-3-21(27)16-22/h2-8,16,20,24,31H,9-15,17-18H2,1H3,(H,28,30)/t20-,24+/m0/s1
comment: The synthesis of this MCH1 receptor antagonist is described in <Reference id=25564/>.
iupac name: N-(3-chlorophenyl)-2-[(3R,4S)-1-[2-(4-hydroxyoxan-4-yl)ethyl]-4-(4-methoxyphenyl)pyrrolidin-3-yl]acetamide
xref: CHEMBL1760248
approved: f
ligand name: pyrrolidine MCHR1 antagonist 1
type: SyntheticOrganicLigand

compound 4b [PMID: 19683441]
in ch i key: FPPIDMVDDSIXTQ-GKPLWNPISA-N
in ch i: InChI=1S/C27H28F2N4O3/c1-3-36-31-26(19-5-6-22(28)23(29)12-19)24-7-4-18(14-30-24)15-33-10-8-27(9-11-33)21-13-25(34)32(2)16-20(21)17-35-27/h4-7,12-14,16H,3,8-11,15,17H2,1-2H3/b31-26+
comment: The synthesis of this MCH1 receptor antagonist is described in <Reference id=25563/>.
approved: f
ligand name: compound 4b [PMID: 19683441]
type: SyntheticOrganicLigand

compound (R)-10h [PMID: 22490048]
in ch i key: HRYQXLHGNOJEHH-GOSISDBHSA-N
in ch i: InChI=1S/C27H32N4O3/c1-17-25(31-27(33)21-6-9-24(10-7-21)34-16-20-4-5-20)11-8-22-14-23(15-30-26(17)22)18(2)28-12-13-29-19(3)32/h6-11,14-15,18,20,28H,4-5,12-13,16H2,1-3H3,(H,29,32)(H,31,33)/t18-/m1/s1
comment: This is compound 10h in <Reference id=25562/>, where the full name of the compound is stated as N-{3-[(1R)-1-{[2-(acetylamino)ethyl]amino}ethyl]-8-methylquinolin-7-yl}-4-(cyclopropylmethoxy)benzamide. It is a potent antagonist of the MCH1 receptor.
iupac name: 4-(cyclopropylmethoxy)-N-{3-[(1R)-1-[(2-acetamidoethyl)amino]ethyl]-8-methylquinolin-7-yl}benzamide
xref: CHEMBL2059513
approved: f
ligand name: compound (R)-10h [PMID: 22490048]
type: SyntheticOrganicLigand

4-arylphthalazin-1(2H)-3,4-Di-F
in ch i key: YVVMAGRTTSOPEO-UHFFFAOYSA-N
in ch i: InChI=1S/C30H30F2N4O2/c1-20(37)33-24-7-4-6-22(18-24)21-12-16-35(17-13-21)14-5-15-36-30(38)26-9-3-2-8-25(26)29(34-36)23-10-11-27(31)28(32)19-23/h2-4,6-11,18-19,21H,5,12-17H2,1H3,(H,33,37)
comment: This is compound 10n in <Reference id=25561/>. It is a potent antagonist of the MCH1 receptor.
iupac name: N-[3-(1-{3-[4-(3,4-difluorophenyl)-1-oxo-1,2-dihydrophthalazin-2-yl]propyl}piperidin-4-yl)phenyl]acetamide
xref: CHEMBL1934835
approved: f
ligand name: 4-arylphthalazin-1(2H)-3,4-Di-F
type: SyntheticOrganicLigand

tanespimycin
in ch i key: AYUNIORJHRXIBJ-HTLBVUBBSA-N
in ch i: InChI=1S/C31H43N3O8/c1-8-12-33-26-21-13-17(2)14-25(41-7)27(36)19(4)15-20(5)29(42-31(32)39)24(40-6)11-9-10-18(3)30(38)34-22(28(21)37)16-23(26)35/h8-11,15-17,19,24-25,27,29,33,36H,1,12-14H2,2-7H3,(H2,32,39)(H,34,38)/b11-9+,18-10+,20-15+/t17-,19+,24+,25+,27-,29+/m1/s1
comment: 17-AAG inhibits the activity of hsp90. The compound is a derivative of the antibacterial geldanamycin. As with other natural products, there is some ambiguity in the absolute stereochemistry annotated by different online resources. PubChem records an alternative isomer with a Z bond at position 12 which has CID 6505803.
iupac name: [(3R,5S,6R,7S,8E,10S,11S,12E,14E)-6-hydroxy-5,11-dimethoxy-3,7,9,15-tetramethyl-16,20,22-trioxo-21-(prop-2-enylamino)-17-azabicyclo[16.3.1]docosa-1(21),8,12,14,18-pentaen-10-yl] carbamate
xref: CHEMBL126955
synonym: 17AAG
synonym: 17-N-allylamino-17-demethoxygeldanamycin
synonym: 17-allylamino-17-demethoxygeldanamycin
synonym: 17-AAG
approved: f
ligand name: tanespimycin
type: NaturalProductLigand

inecalcitol
canonical SMILES: OC1CC(O)CC(=CC=C2CCCC3(C2CCC3C(CC#CC(O)(C)C)C)C)C1
isomeric SMILES: O[C@H]1C[C@H](O)CC(=C/C=C/2/CCC[C@]3([C@@H]2CC[C@@H]3[C@@H](CC#CC(O)(C)C)C)C)C1
in ch i key: HHGRMHMXKPQNGF-WNSNRMDMSA-N
in ch i: InChI=1S/C26H40O3/c1-18(7-5-13-25(2,3)29)23-11-12-24-20(8-6-14-26(23,24)4)10-9-19-15-21(27)17-22(28)16-19/h9-10,18,21-24,27-29H,6-8,11-12,14-17H2,1-4H3/b20-10+/t18-,21-,22-,23-,24-,26-/m1/s1
comment: Inecalcitol is an investigational vitamin D receptor agonist. It is an analogue the naturally occurring active metabolite of vitamin D, <Ligand id=2779/> (calcitrol).
iupac name: (1R,3R)-5-[(2E)-2-[(1R,3aR,7aR)-1-[(2R)-6-hydroxy-6-methylhept-4-yn-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]cyclohexane-1,3-diol
xref: CHEMBL2105107
synonym: TX522
approved: f
ligand name: inecalcitol
type: NaturalProductLigand

nirogacestat
in ch i key: VFCRKLWBYMDAED-REWPJTCUSA-N
in ch i: InChI=1S/C27H41F2N5O/c1-7-8-23(32-20-10-9-18-11-19(28)12-22(29)21(18)13-20)25(35)33-24-14-34(17-31-24)27(5,6)16-30-15-26(2,3)4/h11-12,14,17,20,23,30,32H,7-10,13,15-16H2,1-6H3,(H,33,35)/t20-,23-/m0/s1
comment: Nirogacestat (PF-3084014) is compound 14f in <Reference id=25537/> where it is described as a centrally active γ-secretase inhibitor. PF-3084014 also acts as an inhibitor of the NOTCH signalling pathway, and can promote cell cycle arrest and induce apoptosis in leukemia cells <Reference id=25539/>. As such, it was predicted to enable improved efficacy of the standard chemotherapy used in chronic lymphocytic leukemia (CLL) treatment <Reference id=25538/>.
iupac name: (2S)-2-[[(2S)-6,8-difluoro-1,2,3,4-tetrahydronaphthalen-2-yl]amino]-N-[1-[1-(2,2-dimethylpropylamino)-2-methylpropan-2-yl]imidazol-4-yl]pentanamide
xref: CHEMBL1770916
synonym: Z-3181
synonym: PF-03084014
synonym: PF3084014
approved: f
ligand name: nirogacestat
type: SyntheticOrganicLigand

daporinad
isomeric SMILES: O=C(/C=C/c1cccnc1)NCCCCC1CCN(CC1)C(=O)c1ccccc1
in ch i key: KPBNHDGDUADAGP-VAWYXSNFSA-N
in ch i: InChI=1S/C24H29N3O2/c28-23(12-11-21-8-6-15-25-19-21)26-16-5-4-7-20-13-17-27(18-14-20)24(29)22-9-2-1-3-10-22/h1-3,6,8-12,15,19-20H,4-5,7,13-14,16-18H2,(H,26,28)/b12-11+
comment: FK866 is a highly specific non-competitive inhibitor of nicotinamide phosphoribosyltransferase (NAMPT; P43490) <Reference id=25535/>, an enzyme required for the biosynthesis of nicotinamide adenine dinucleotide (NAD+).
iupac name: (E)-N-[4-[1-(benzoyl)piperidin-4-yl]butyl]-3-pyridin-3-ylprop-2-enamide
xref: CHEMBL566757
synonym: FK866
synonym: FK-866
synonym: APO-866
approved: f
ligand name: daporinad
type: SyntheticOrganicLigand

RGB-286638
in ch i key: XLSYZSRXVVCHLS-UHFFFAOYSA-N
in ch i: InChI=1S/C29H35N7O4/c1-39-16-13-34-9-11-35(12-10-34)19-20-5-7-21(8-6-20)26-25-27(32-31-26)22-3-2-4-23(24(22)28(25)37)30-29(38)33-36-14-17-40-18-15-36/h2-8H,9-19H2,1H3,(H,31,32)(H2,30,33,38)
comment: RGB-286638 is a multi-targeted kinase inhibitor. It inhibits transcriptional-type CDKs (cyclin dependent kinases) such as CDK9, to achieve an anti-multiple myeloma effect which is independent of p53 status <Reference id=25533/>, providing a proof of concept which could lead to the development of compounds with activity in p53 deleted multiple myeloma. A Phase I safety and tolerability study, NCT01168882, was withdrawn from ClinicalTrials.gov (2012), although results of this study have been published.<Reference id=25534/>.
iupac name: 1-[3-[4-[[4-(2-methoxyethyl)piperazin-1-yl]methyl]phenyl]-4-oxo-1H-indeno[2,1-d]pyrazol-5-yl]-3-morpholin-4-ylurea
synonym: RGB 286638
synonym: RGB286638
approved: f
ligand name: RGB-286638
type: SyntheticOrganicLigand

izorlisib
in ch i key: JEGHXKRHKHPBJD-UHFFFAOYSA-N
in ch i: InChI=1S/C15H19N7O3S/c1-26(23,24)22-3-2-11-12(10-8-17-14(16)18-9-10)19-15(20-13(11)22)21-4-6-25-7-5-21/h8-9H,2-7H2,1H3,(H2,16,17,18)
comment: Izorlisib (MEN1611 and formerly CH5132799) is described as a potent, orally available class I PI3K inhibitor <Reference id=25532/>. Clinical development of CH5132799 has been licenced to Menarini Pharma from Chugai Pharmaceutical Co, hence the change in research code. The chemical structure of MEN1611 is identical to that which was submitted to the WHO for the INN izorlisib (proposed INN list 126, Jan 2022).
iupac name: 5-[7-methanesulfonyl-2-(morpholin-4-yl)-5H,6H,7H-pyrrolo[2,3-d]pyrimidin-4-yl]pyrimidin-2-amine
xref: CHEMBL1684984
synonym: CH-5132799
synonym: CH 5132799
synonym: CH5132799
synonym: MEN1611
synonym: MEN-1611
approved: f
ligand name: izorlisib
type: SyntheticOrganicLigand

conopeptide Y-PI1
in ch i key: MNFKIRAJURGUGP-CWBJURCASA-N
comment: Conopeptide from Conus planorbis (Planorbis cone).
approved: f
ligand name: conopeptide Y-PI1
type: PeptideLigand

brigatinib
in ch i key: AILRADAXUVEEIR-UHFFFAOYSA-N
comment: Brigatinib (AP26113) is a phosphine oxide-containing drug developed as a treatment for cancers driven by anaplastic lymphoma kinase (ALK) rearrangements <Reference id=30970/> or by T790M gatekeeper mutant EGFR. It is an orally available inhibitor.
iupac name: 5-chloro-4-N-(2-dimethylphosphorylphenyl)-2-N-[2-methoxy-4-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]phenyl]pyrimidine-2,4-diamine
xref: CHEMBL3545311
synonym: AP-26113
synonym: AP26113
synonym: compound 11q [PMID: 27144831]
synonym: Alunbrig®
approved: t
ligand name: brigatinib
type: SyntheticOrganicLigand

ASP-3026
in ch i key: MGGBYMDAPCCKCT-UHFFFAOYSA-N
in ch i: InChI=1S/C29H40N8O3S/c1-21(2)41(38,39)27-8-6-5-7-25(27)33-29-31-20-30-28(34-29)32-24-10-9-23(19-26(24)40-4)36-13-11-22(12-14-36)37-17-15-35(3)16-18-37/h5-10,19-22H,11-18H2,1-4H3,(H2,30,31,32,33,34)
comment: ASP-3026 is a second generation ALK inhibitor designed to target ALK rearrangements which are the oncogenic drivers of some non-small cell lung cancers (NSCLCs) and T-cell lymphomas known as ALK- expressing anaplastic large-cell lymphoma (ALK+ALCL) .
iupac name: 2-N-[2-methoxy-4-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]phenyl]-4-N-(2-propan-2-ylsulfonylphenyl)-1,3,5-triazine-2,4-diamine
synonym: ASP3026
synonym: ASP 3026
approved: f
ligand name: ASP-3026
type: SyntheticOrganicLigand

alectinib
in ch i key: KDGFLJKFZUIJMX-UHFFFAOYSA-N
in ch i: InChI=1S/C30H34N4O2/c1-4-20-16-23-24(17-26(20)34-9-7-21(8-10-34)33-11-13-36-14-12-33)30(2,3)29-27(28(23)35)22-6-5-19(18-31)15-25(22)32-29/h5-6,15-17,21,32H,4,7-14H2,1-3H3
comment: Alectinib is a second generation ALK inhibitor. It was developed to inhibit the expression of the mutated ALK gene that causes growth of some non-small cell lung cancers, in patients whose cancer has become resistant to the older ALK inhibitor, <Ligand id=4903/> <Reference id=25508/><Reference id=25512/>. However, additional mutations may develop which confer alecitinib resistance <Reference id=25506/>. Cells harbouring these novel mutations are reported to be sensitive to <Ligand id=7397/> and other next-generation ALK tyrosine kinase inhibitors <Reference id=25506/>. The identification of the mechanisms by which acquired tumour resistance occurs highlights the importance of being able to use the correct drug for the correct patient to maximise the clinical benefit <Reference id=25513/> The design and synthesis of alectinib (CH5424802) is described in <Reference id=25512/>.
iupac name: 9-ethyl-6,6-dimethyl-8-(4-morpholin-4-ylpiperidin-1-yl)-11-oxo-5H-benzo[b]carbazole-3-carbonitrile
xref: CHEMBL1738797
synonym: CH5424802
synonym: AF802
synonym: Alecensa®
approved: t
ligand name: alectinib
type: SyntheticOrganicLigand

rucaparib
in ch i key: HMABYWSNWIZPAG-UHFFFAOYSA-N
in ch i: InChI=1S/C19H18FN3O/c1-21-10-11-2-4-12(5-3-11)18-14-6-7-22-19(24)15-8-13(20)9-16(23-18)17(14)15/h2-5,8-9,21,23H,6-7,10H2,1H3,(H,22,24)
comment: Rucaparib is an orally active poly(ADP-ribose)polymerase (PARP) inhibitor with anti-cancer activity <Reference id=25470/>. It was developed by Clovis Oncology. PARP inhibitors are known to enhance efficacy of anti-cancer therapies such as DNA alkylating agents, topoisomerase I poisons, and ionizing radiation. Note that in the Thomas et al. paper <Reference id=25470/>, AG014699 refers to the phosphate salt and AG14447 to the parent molecule. Rucaparib was accepted for FDA priority review for the treatment of advanced ovarian cancer harbouring mutant BRCA (August 2016). Note: <Ligand id=7519/> was the first PARP inhibitor to be approved for clinical use.
xref: CHEMBL1173055
synonym: AG-014699
synonym: PF-01367338
synonym: AG14447
synonym: AG014699
synonym: Rubraca®
approved: t
ligand name: rucaparib
type: SyntheticOrganicLigand

AZ13483342
canonical SMILES: COc1ccc2c(c1)c(C)cc(n2)NCCCNCc1cscc1
isomeric SMILES: COc1ccc2c(c1)c(C)cc(n2)NCCCNCc1cscc1
in ch i key: ZDKZIFSAJUTJSK-UHFFFAOYSA-N
in ch i: InChI=1S/C19H23N3OS/c1-14-10-19(22-18-5-4-16(23-2)11-17(14)18)21-8-3-7-20-12-15-6-9-24-13-15/h4-6,9-11,13,20H,3,7-8,12H2,1-2H3,(H,21,22)
comment: From patent searching this compound would appear to be Example 2 from patent WO 2004004726 A1, which maps chemically to PubChem CID 9927967. This is the structure we show here. AZ13483342 is included in AstaZeneca's Open Innovation Pharmacology Toolbox. It was developed as an antagonist of the melanin concentrating hormone receptor 1 (MCH1) as a potential diabetes therapeutic <Reference id=25466/>. AZ13483342 is compound 7 in <Reference id=25467/>.
iupac name: N-(6-methoxy-4-methylquinolin-2-yl)-N'-(thiophen-3-ylmethyl)propane-1,3-diamine
xref: CHEMBL400679
synonym: AZ 13483342
synonym: AZ-13483342
approved: f
ligand name: AZ13483342
type: SyntheticOrganicLigand

AZ12419304
in ch i key: QOTCLGLPFWDADD-UHFFFAOYSA-N
in ch i: InChI=1S/C23H18F3N5O2/c1-13-3-4-14(21(32)30-16-7-8-27-20(11-16)23(24,25)26)9-19(13)29-15-5-6-18-17(10-15)22(33)31(2)12-28-18/h3-12,29H,1-2H3,(H,27,30,32)
comment: From patent searching it looks likely that this compound is Example 9 from patent WO2007113558 A2, which gives affinity data in line with that provided on the compound's page in AstaZeneca's Open Innovation Pharmacology Toolbox <Reference id=25465/>. Converting the chemical name (4-methyl-3-[(3-methyl-4-oxoquinazolin-6-yl)amino]-N-[2-(trifluoromethyl)pyridin-4-yl]benzamide) to smiles leads to PubChem CID 16750158. This is the structure we show here.
iupac name: 4-methyl-3-[(3-methyl-4-oxoquinazolin-6-yl)amino]-N-[2-(trifluoromethyl)pyridin-4-yl]benzamide
synonym: AZ 12419304
synonym: AZ-12419304
approved: f
ligand name: AZ12419304
type: SyntheticOrganicLigand

GDC-0152
in ch i key: WZRFLSDVFPIXOV-LRQRDZAKSA-N
in ch i: InChI=1S/C25H34N6O3S/c1-16(26-2)22(32)27-21(18-12-7-4-8-13-18)25(34)31-15-9-14-19(31)23(33)28-24-20(29-30-35-24)17-10-5-3-6-11-17/h3,5-6,10-11,16,18-19,21,26H,4,7-9,12-15H2,1-2H3,(H,27,32)(H,28,33)/t16-,19-,21-/m0/s1
comment: GDC-0152 is reported to be a potent small-molecule antagonist of inhibitor of apoptosis (IAP) proteins <Reference id=25464/>. The compound is a Smac mimetic, and antagonises binding of caspases to BIR domains of IAP proteins. This action restores apoptosis.
iupac name: (2S)-1-[(2S)-2-cyclohexyl-2-[[(2S)-2-(methylamino)propanoyl]amino]acetyl]-N-(4-phenylthiadiazol-5-yl)pyrrolidine-2-carboxamide
xref: CHEMBL2063869
synonym: GDC 0152
synonym: GDC0152
approved: f
ligand name: GDC-0152
type: SyntheticOrganicLigand

SM-337
in ch i key: YBYZHVZWINISJO-XPSCAIQQSA-N
in ch i: InChI=1S/C35H41N5O4/c1-24(36-2)33(42)37-29-23-39(31(41)22-25-12-6-3-7-13-25)21-20-28-18-19-30(40(28)35(29)44)34(43)38-32(26-14-8-4-9-15-26)27-16-10-5-11-17-27/h3-17,24,28-30,32,36H,18-23H2,1-2H3,(H,37,42)(H,38,43)/t24-,28+,29-,30-/m0/s1
comment: SM-377 is compound 6 in <Reference id=25463/>. SM-337 is a potent, orally bioavailable Smac mimetic which acts as an antagonist of caspase binding to IAP family members, XIAP, cIAP1 and cIAP2 <Reference id=25463/>.
iupac name: (5S,8S,10aR)-N-benzhydryl-5-[[(2S)-2-(methylamino)propanoyl]amino]-6-oxo-3-(2-phenylacetyl)-1,2,4,5,8,9,10,10a-octahydropyrrolo[1,2-a][1,5]diazocine-8-carboxamide
xref: CHEMBL504559
approved: f
ligand name: SM-337
type: SyntheticOrganicLigand

saracatinib
in ch i key: OUKYUETWWIPKQR-UHFFFAOYSA-N
in ch i: InChI=1S/C27H32ClN5O5/c1-32-6-8-33(9-7-32)10-13-35-19-14-21-24(23(15-19)38-18-4-11-34-12-5-18)27(30-16-29-21)31-25-20(28)2-3-22-26(25)37-17-36-22/h2-3,14-16,18H,4-13,17H2,1H3,(H,29,30,31)
comment: Saracatinib was developed as an inhibitor of Src family tyrosine kinases. This compound is now included in AstaZeneca's Open Innovation Pharmacology Toolbox. Note that some bioactivity data may be associated with the difumarate salt (PubChem CID 44195703). Saracatinib (AZD0530) is compound 33 in <Reference id=25460/>.
iupac name: N-(5-chloro-1,3-benzodioxol-4-yl)-7-[2-(4-methylpiperazin-1-yl)ethoxy]-5-(oxan-4-yloxy)quinazolin-4-amine
xref: CHEMBL217092
synonym: AZD0530
synonym: AZD-0530
approved: f
ligand name: saracatinib
type: SyntheticOrganicLigand

xevinapant
in ch i key: LSXUTRRVVSPWDZ-MKKUMYSQSA-N
in ch i: InChI=1S/C32H43N5O4/c1-21(2)19-28(38)36-18-17-25-15-16-27(37(25)32(41)26(20-36)34-30(39)22(3)33-4)31(40)35-29(23-11-7-5-8-12-23)24-13-9-6-10-14-24/h5-14,21-22,25-27,29,33H,15-20H2,1-4H3,(H,34,39)(H,35,40)/t22-,25+,26-,27-/m0/s1
comment: Xevinapant (formerly AT-406, Debio 1143) is an orally available inhibitor of IAPs (inhibitor of apoptosis proteins), that is in development for anticancer potential. It was initially developed by Ascenta Therapeutics, and was originally progressed by Debiopharm. Merck in-licensed the asset when it was in late stage development. Structurally, xevinapant is a small molecule SMAC mimetic; SMAC being an endogenous IAP antagonist. Inhibition of IAPs which are often overexpressed in cancer cells (blocking apoptosis) leads to cancer cell death. SMAC mimetic-induced cancer cell death appears to involve multiple pathways, including re-activation of the apoptotic pathway, and/or ubiquitin-directed degradation of IAPs, which promotes TNFα/caspase-8-induced cell death <Reference id=40537/><Reference id=40538/>.
iupac name: (5S,8S,10aR)-N-benzhydryl-5-[[(2S)-2-(methylamino)propanoyl]amino]-3-(3-methylbutanoyl)-6-oxo-1,2,4,5,8,9,10,10a-octahydropyrrolo[1,2-a][1,5]diazocine-8-carboxamide
xref: CHEMBL2158051
synonym: AT406
synonym: QCR-136
synonym: SM 406
synonym: Debio-1143
synonym: Debio1143
synonym: AT 406
approved: f
ligand name: xevinapant
type: SyntheticOrganicLigand

AZD5904
canonical SMILES: O=c1[nH]c(=S)n(c2c1[nH]cn2)CC1CCCO1
isomeric SMILES: O=c1[nH]c(=S)n(c2c1[nH]cn2)C[C@H]1CCCO1
in ch i key: RSPDBEVKURKEII-ZCFIWIBFSA-N
in ch i: InChI=1S/C10H12N4O2S/c15-9-7-8(12-5-11-7)14(10(17)13-9)4-6-2-1-3-16-6/h5-6H,1-4H2,(H,11,12)(H,13,15,17)/t6-/m1/s1
comment: AZD5904 is compound TX4 in <Reference id=25432/>. AZD5904 was developed as a myeloperoxidase (MPO; P05164) inhibitor, but was abandoned as a clinical candidate for the treatment of inflammatory conditions involving oxidative stress. This compound is now included in AstaZeneca's Open Innovation Pharmacology Toolbox.
iupac name: 3-[[(2R)-oxolan-2-yl]methyl]-2-sulfanylidene-7H-purin-6-one
synonym: AZD 5904
synonym: AZD-5904
approved: f
ligand name: AZD5904
type: SyntheticOrganicLigand

AZ12971554
in ch i key: GMKHQRCPNMGCIX-ZWKOTPCHSA-N
comment: This structure was drawn from <Reference id=25430/>. AZ12971554 is an investigational direct thrombin inhibitor. Direct thrombin inhibitors are considered to exhibit improved clinical properties compared to the historically used anticoagulant <Ligand id=6853/>. This compound is now included in AstaZeneca's Open Innovation Pharmacology Toolbox.
iupac name: (5S)-N-{[5-chloro-2-(1H-1,2,3,4-tetrazol-1-yl)phenyl]methyl}-1-[(2R)-2-(4-fluorophenyl)-2-hydroxyacetyl]-4,5-dihydro-1H-pyrazole-5-carboxamide
synonym: AZ 12971554
synonym: AZ-12971554
approved: f
ligand name: AZ12971554
type: SyntheticOrganicLigand

compound 10 [PMID: 15482906]
canonical SMILES: Fc1cc(Oc2cccnc2)cc(c1)n1nnc(n1)c1ccccn1
isomeric SMILES: Fc1cc(Oc2cccnc2)cc(c1)n1nnc(n1)c1ccccn1
in ch i key: IQSMPFFGKFZZMI-UHFFFAOYSA-N
in ch i: InChI=1S/C17H11FN6O/c18-12-8-13(10-15(9-12)25-14-4-3-6-19-11-14)24-22-17(21-23-24)16-5-1-2-7-20-16/h1-11H
iupac name: 2-{2-[3-fluoro-5-(pyridin-3-yloxy)phenyl]-2H-1,2,3,4-tetrazol-5-yl}pyridine
xref: CHEMBL186151
approved: f
ligand name: compound 10 [PMID: 15482906]
type: SyntheticOrganicLigand

AZD8165
in ch i key: YUHNXUAATAMVKD-PZJWPPBQSA-N
comment: This structure was drawn from <Reference id=25430/>.
iupac name: (1R)-2-[(5S)-5-({[5-chloro-2-(1H-1,2,3,4-tetrazol-1-yl)phenyl]methyl}carbamoyl)-4,5-dihydro-1H-pyrazol-1-yl]-1-(4-fluorophenyl)-2-oxoethyl propanoate
synonym: AZD 8165
synonym: AZD-8165
approved: f
ligand name: AZD8165
type: SyntheticOrganicLigand

AZ12260493
in ch i key: IVANYIPLGFVBGR-UHFFFAOYSA-N
in ch i: InChI=1S/C24H29N3O3S/c1-24(2,3)27-23(28)21(22(31(27,29)30)18-10-6-4-7-11-18)25-19-12-14-20(15-13-19)26-16-8-5-9-17-26/h4,6-7,10-15,25H,5,8-9,16-17H2,1-3H3
comment: AZ12260493 was developed as an agonist of the liver X receptors α and β and investigated as a treatment for dyslipidaemia. This compound is now included in AstaZeneca's Open Innovation Pharmacology Toolbox.
iupac name: 2-tert-butyl-1,1-dioxo-5-phenyl-4-[(4-piperidin-1-ylphenyl)amino]-1,2-thiazol-3-one
synonym: AZ 12260493
synonym: AZ-12260493
approved: f
ligand name: AZ12260493
type: SyntheticOrganicLigand

TTA-A2
in ch i key: GEYDMBNDOVPFJL-CYBMUJFWSA-N
in ch i: InChI=1S/C20H21F3N2O2/c1-13(18-9-8-17(11-24-18)27-12-20(21,22)23)25-19(26)10-14-2-4-15(5-3-14)16-6-7-16/h2-5,8-9,11,13,16H,6-7,10,12H2,1H3,(H,25,26)/t13-/m1/s1
iupac name: 2-(4-cyclopropylphenyl)-N-[(1R)-1-[5-(2,2,2-trifluoroethoxy)pyridin-2-yl]ethyl]acetamide
xref: CHEMBL1684954
approved: f
ligand name: TTA-A2
type: SyntheticOrganicLigand

TTA-P2
in ch i key: DKNDOKIVCXTFHJ-HNNXBMFYSA-N
iupac name: 3,5-dichloro-N-[[1-[[(4S)-2,2-dimethyloxan-4-yl]methyl]-4-fluoropiperidin-4-yl]methyl]benzamide
xref: CHEMBL488817
approved: f
ligand name: TTA-P2
type: SyntheticOrganicLigand

AZ11657312 (salt free)
in ch i key: XYNNEMHCLNODBL-UHFFFAOYSA-N
in ch i: InChI=1S/C26H35N3O3/c1-16-2-3-20(25(31)29-14-21-12-27-13-22(15-29)32-21)7-23(16)28-24(30)11-26-8-17-4-18(9-26)6-19(5-17)10-26/h2-3,7,17-19,21-22,27H,4-6,8-15H2,1H3,(H,28,30)
comment: The monohydrochloride is described in the article <Reference id=25424/>, which provides the IUPAC name, 2-(adamantan-1-yl)-N-[2-methyl-5-(9-oxa-3,7-diazabicyclo[3.3.1]non-3-ylcarbonyl)phenyl]acetamide monohydrochloride, for this compound. We represent the molecule here, without the hydrochloride. AZ11657312 is an antagonist of the purinergic receptor 2X, ligand-gated ion channel 7 (P2X7) which is implicated the molecular mechanisms underlying pain and inflammation, as its activation leads to the release of proinflammatory cytokines such as interleukin (IL)-1, tumor necrosis factor (TNF)-α, and IL-6 <Reference id=15545/><Reference id=25426/>. AZ11657312 has been investigated as an antiinflammatory treatment for conditions such as COPD, Crohn's disease and osteo- and rheumatoid arthritis. This compound is now included in AstaZeneca's Open Innovation Pharmacology Toolbox.
iupac name: 2-(1-adamantyl)-N-[2-methyl-5-(9-oxa-3,7-diazabicyclo[3.3.1]nonane-3-carbonyl)phenyl]acetamide
xref: CHEMBL550637
approved: f
ligand name: AZ11657312 (salt free)
type: SyntheticOrganicLigand

UNC9994
in ch i key: URYZTMIOHYGTNJ-UHFFFAOYSA-N
comment: UNC9994 is an analog of <Ligand id=34/> and is a β-arrestin–biased dopamine D2 receptor ligand <Reference id=25195/>
iupac name: 5-{3-[4-(2,3-dichlorophenyl)piperidin-1-yl]propoxy}-1,3-benzothiazole
xref: CHEMBL2165138
approved: f
ligand name: UNC9994
type: SyntheticOrganicLigand

ABT-639
in ch i key: AGPIHNZOZNKRGT-CYBMUJFWSA-N
iupac name: 5-[(8aR)-3,4,6,7,8,8a-hexahydro-1H-pyrrolo[1,2-a]pyrazine-2-carbonyl]-4-chloro-2-fluoro-N-(2-fluorophenyl)benzenesulfonamide
synonym: ABT639
synonym: ABT 639
approved: f
ligand name: ABT-639
type: SyntheticOrganicLigand

ML218
in ch i key: GSJIGYLGKSBYBC-OSYLJGHBSA-N
in ch i: InChI=1S/C19H26Cl2N2O/c1-19(2,3)4-5-23-10-16-15(17(16)11-23)9-22-18(24)12-6-13(20)8-14(21)7-12/h6-8,15-17H,4-5,9-11H2,1-3H3,(H,22,24)/t15-,16-,17+
comment: This compound is represented in PubChem with slightly different stereochemistry by CID 45115620.
iupac name: 3,5-dichloro-N-[[(1R,5S)-3-(3,3-dimethylbutyl)-3-azabicyclo[3.1.0]hexan-6-yl]methyl]benzamide
xref: CHEMBL1732375
synonym: ML-218
synonym: ML 218
approved: f
ligand name: ML218
type: SyntheticOrganicLigand

osimertinib
in ch i key: DUYJMQONPNNFPI-UHFFFAOYSA-N
in ch i: InChI=1S/C28H33N7O2/c1-7-27(36)30-22-16-23(26(37-6)17-25(22)34(4)15-14-33(2)3)32-28-29-13-12-21(31-28)20-18-35(5)24-11-9-8-10-19(20)24/h7-13,16-18H,1,14-15H2,2-6H3,(H,30,36)(H,29,31,32)
comment: Osimertinib (AZD9291) is a third-generation, potent, selective and irreversible inhibitor of the epidermal growth factor receptor (EGFR) tyrosine kinase bearing mutations which either sensitise the receptor, or cause drug resistance (eg the T790M mutation) <Reference id=30938/>. The compound is less effective against the wild-type receptor. This compound is included in AstaZeneca's Open Innovation Pharmacology Toolbox. There are reports of acquired resistance to osimertinib with tumours developing the C797S <Reference id=31221/><Reference id=31223/> and L718Q mutations <Reference id=31222/> . Third-generation mutant EGFR inhibitors are being developed to circumvent dose-limiting WT EGFR-driven toxicities such as gastrointestinal toxicity and rash. The progress being made in developing advanced generation EGFR inhibitors is discussed by Yu and Riely (2013) <Reference id=26332/> and Ou and Soo (2015) <Reference id=31220/>.
iupac name: N-[2-[2-(dimethylamino)ethyl-methylamino]-4-methoxy-5-[[4-(1-methylindol-3-yl)pyrimidin-2-yl]amino]phenyl]prop-2-enamide
synonym: AZD-9291
synonym: AZD 9291
synonym: AZD9291
synonym: mereletinib (obsolete INN)
synonym: Tagrisso®
approved: t
ligand name: osimertinib
type: SyntheticOrganicLigand

Z944
in ch i key: JOCLITFYIMJMNK-UHFFFAOYSA-N
iupac name: N-[[1-[2-(tert-butylamino)-2-oxoethyl]piperidin-4-yl]methyl]-3-chloro-5-fluorobenzamide
synonym: Z 944
synonym: Z-944
approved: f
ligand name: Z944
type: SyntheticOrganicLigand

sapitinib
in ch i key: DFJSJLGUIXFDJP-UHFFFAOYSA-N
comment: Sapitinib is an inhibitor of all members of the epidermal growth factor receptor (EGFR) receptor tyrosine kinase family <Reference id=25420/> and was investigated as a potential oncology therapeutic. This compound is now included in AstaZeneca's Open Innovation Pharmacology Toolbox.
iupac name: 2-[4-[4-[(3-chloro-2-fluorophenyl)amino]-7-methoxyquinazolin-6-yl]oxypiperidin-1-yl]-N-methylacetamide
xref: CHEMBL2408045
synonym: AZD8931
synonym: AZD-8931
approved: f
ligand name: sapitinib
type: SyntheticOrganicLigand

AZD8542
in ch i key: SMQVBAGSZVHCJP-UHFFFAOYSA-N
in ch i: InChI=1S/C25H24N4O2/c1-17-12-18(2)23(13-22(17)24-14-29(3)16-27-24)28-25(30)19-7-9-21(10-8-19)31-15-20-6-4-5-11-26-20/h4-14,16H,15H2,1-3H3,(H,28,30)
comment: AZD8542 was developed as an antagonist of Smoothened (SMO), with potential as an oncology therapeutic <Reference id=25419/>. This compound is now included in AstaZeneca's Open Innovation Pharmacology Toolbox.
iupac name: N-[2,4-dimethyl-5-(1-methylimidazol-4-yl)phenyl]-4-(pyridin-2-ylmethoxy)benzamide
synonym: AZD 8542
synonym: AZD-8542
approved: f
ligand name: AZD8542
type: SyntheticOrganicLigand

AZD8329
in ch i key: XWBXJBSVYVJAMZ-UHFFFAOYSA-N
in ch i: InChI=1S/C25H31N3O3/c1-25(2,3)22-20(13-26-28(22)19-6-4-16(5-7-19)24(30)31)23(29)27-21-17-9-14-8-15(11-17)12-18(21)10-14/h4-7,13-15,17-18,21H,8-12H2,1-3H3,(H,27,29)(H,30,31)
comment: AZD8329 is an inhibitor of 11-beta-hydroxysteroid dehydrogenase type 1 (11β-HSD1). This compound is included in AstaZeneca's Open Innovation Pharmacology Toolbox.
iupac name: 4-[4-(2-adamantylcarbamoyl)-5-tert-butylpyrazol-1-yl]benzoic acid
xref: CHEMBL2177609
synonym: AZD-8329
synonym: AZD 8329
approved: f
ligand name: AZD8329
type: SyntheticOrganicLigand

AZD8055
in ch i key: KVLFRAWTRWDEDF-IRXDYDNUSA-N
in ch i: InChI=1S/C25H31N5O4/c1-16-14-33-10-8-29(16)24-20-5-6-21(18-4-7-22(32-3)19(12-18)13-31)26-23(20)27-25(28-24)30-9-11-34-15-17(30)2/h4-7,12,16-17,31H,8-11,13-15H2,1-3H3/t16-,17-/m0/s1
comment: AZD8055 is an inhibitor of the mammalian target of rapamycin (mTOR) kinase <Reference id=25412/>. AZD8055 was investigated as a potential treatment for various types of relapsed and/or refactory cancer. This compound is now included in AstaZeneca's Open Innovation Pharmacology Toolbox.
iupac name: [5-[2,4-bis[(3S)-3-methylmorpholin-4-yl]pyrido[2,3-d]pyrimidin-7-yl]-2-methoxyphenyl]methanol
xref: CHEMBL1801204
synonym: AZD-8055
synonym: AZD 8055
approved: f
ligand name: AZD8055
type: SyntheticOrganicLigand

AZD7762
in ch i key: IAYGCINLNONXHY-LBPRGKRZSA-N
in ch i: InChI=1S/C17H19FN4O2S/c18-11-4-1-3-10(7-11)14-8-13(22-17(19)24)15(25-14)16(23)21-12-5-2-6-20-9-12/h1,3-4,7-8,12,20H,2,5-6,9H2,(H,21,23)(H3,19,22,24)/t12-/m0/s1
comment: AZD7762 was developed as an inhibitor of the checkpoint kinases, Chk1 and Chk2 <Reference id=25410/>, and was investigated as a therapeutic for solid and haematological malignancies. This compound is now included in AstaZeneca's Open Innovation Pharmacology Toolbox.
iupac name: 3-(carbamoylamino)-5-(3-fluorophenyl)-N-[(3S)-piperidin-3-yl]thiophene-2-carboxamide
xref: CHEMBL2041933
synonym: AZD 7762
synonym: AZD-7762
approved: f
ligand name: AZD7762
type: SyntheticOrganicLigand

AZD7325
canonical SMILES: CCCNC(=O)c1nnc2c(c1N)cccc2c1c(F)cccc1OC
isomeric SMILES: CCCNC(=O)c1nnc2c(c1N)cccc2c1c(F)cccc1OC
in ch i key: KYDURMHFWXCKMW-UHFFFAOYSA-N
in ch i: InChI=1S/C19H19FN4O2/c1-3-10-22-19(25)18-16(21)12-7-4-6-11(17(12)23-24-18)15-13(20)8-5-9-14(15)26-2/h4-9H,3,10H2,1-2H3,(H2,21,23)(H,22,25)
comment: AZD7325 was developed as a positive allosteric modulator of the GABAA α2 and α3 channels and was investigated as a treatment for generalised anxiety disorder. This compound is now included in AstaZeneca's Open Innovation Pharmacology Toolbox.
iupac name: 4-amino-8-(2-fluoro-6-methoxyphenyl)-N-propylcinnoline-3-carboxamide
xref: CHEMBL1783282
synonym: AZD-7325
synonym: AZD 7325
approved: f
ligand name: AZD7325
type: SyntheticOrganicLigand

AZD6495
in ch i key: IBHNEKVLDKCEQY-UHFFFAOYSA-N
in ch i: InChI=1S/C23H25F2N5O2/c1-3-32-21-12-19-15(11-20(21)30-8-6-29(2)7-9-30)22(16(13-27-19)23(26)31)28-18-5-4-14(24)10-17(18)25/h4-5,10-13H,3,6-9H2,1-2H3,(H2,26,31)(H,27,28)
comment: AZD6495 is an investigational inhibitor of the colony stimulating factor-1 receptor (CSF-1R) tyrosine kinase <Reference id=25407/>. It was developed as an antineoplastic agent. This compound is now included in AstaZeneca's Open Innovation Pharmacology Toolbox.
iupac name: 4-[(2,4-difluorophenyl)amino]-7-ethoxy-6-(4-methylpiperazin-1-yl)quinoline-3-carboxamide
xref: CHEMBL481806
synonym: AZD 6495
synonym: AZD-6495
approved: f
ligand name: AZD6495
type: SyntheticOrganicLigand

AZD5582
in ch i key: WLMCRYCCYXHPQF-ZVMUOSSASA-N
in ch i: InChI=1S/C58H78N8O8/c1-37(59-3)53(67)61-49(39-21-9-7-10-22-39)57(71)65-31-19-29-45(65)55(69)63-51-43-27-15-13-25-41(43)35-47(51)73-33-17-5-6-18-34-74-48-36-42-26-14-16-28-44(42)52(48)64-56(70)46-30-20-32-66(46)58(72)50(40-23-11-8-12-24-40)62-54(68)38(2)60-4/h13-16,25-28,37-40,45-52,59-60H,7-12,19-24,29-36H2,1-4H3,(H,61,67)(H,62,68)(H,63,69)(H,64,70)/t37-,38-,45-,46-,47+,48+,49-,50-,51-,52-/m0/s1
comment: AZD5582 is a Smac mimetic which acts as an antagonist of the inhibitor of apoptosis proteins (IAPs). It was investigated as a potential therapeutic for solid tumours. This compound is now included in AstaZeneca's Open Innovation Pharmacology Toolbox. The chemical structure represented here was drawn from <Reference id=25406/>, where it is compound 14.
xref: CHEMBL3108827
synonym: AZD 5582
synonym: AZD-5582
approved: f
ligand name: AZD5582
type: SyntheticOrganicLigand

capivasertib
in ch i key: JDUBGYFRJFOXQC-KRWDZBQOSA-N
in ch i: InChI=1S/C21H25ClN6O2/c22-15-3-1-14(2-4-15)17(6-12-29)27-20(30)21(23)7-10-28(11-8-21)19-16-5-9-24-18(16)25-13-26-19/h1-5,9,13,17,29H,6-8,10-12,23H2,(H,27,30)(H,24,25,26)/t17-/m0/s1
comment: Capivasertib (AZD5363) was developed as an inhibitor of the AKT serine/threonine protein kinases <Reference id=19787/>, and was investigated as a potential therapeutic for solid and haematological malignancies. This compound is now included in AstaZeneca's Open Innovation Pharmacology Toolbox.
iupac name: 4-amino-N-[(1S)-1-(4-chlorophenyl)-3-hydroxypropyl]-1-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxamide
xref: CHEMBL2325741
synonym: AZD5363
synonym: AZD 5363
synonym: AZD-5363
synonym: cc-638
approved: f
ligand name: capivasertib
type: SyntheticOrganicLigand

AZD4877
in ch i key: SMFXSYMLJDHGIE-UHFFFAOYSA-N
in ch i: InChI=1S/C28H33N5O2S/c1-18(2)24(32(16-8-15-29)27(34)22-13-11-19(3)12-14-22)25-30-26-23(20(4)31-36-26)28(35)33(25)17-21-9-6-5-7-10-21/h5-7,9-14,18,24H,8,15-17,29H2,1-4H3
comment: AZD4877 was developed as an inhibitor of the kinesin spindle protein KIF11 (aka Eg5) and was investigated as a potential treatment for haematopoietic and solid malignancies. This compound is now included in AstaZeneca's Open Innovation Pharmacology Toolbox.
iupac name: N-(3-aminopropyl)-4-methyl-N-[2-methyl-1-[3-methyl-4-oxo-5-(phenylmethyl)-[1,2]thiazolo[5,4-d]pyrimidin-6-yl]propyl]benzamide
xref: CHEMBL1829433
synonym: AZD-4877
synonym: AZD 4877
synonym: cc-722
approved: f
ligand name: AZD4877
type: SyntheticOrganicLigand

AZD4547
in ch i key: VRQMAABPASPXMW-HDICACEKSA-N
in ch i: InChI=1S/C26H33N5O3/c1-17-15-31(16-18(2)27-17)22-9-6-20(7-10-22)26(32)28-25-13-21(29-30-25)8-5-19-11-23(33-3)14-24(12-19)34-4/h6-7,9-14,17-18,27H,5,8,15-16H2,1-4H3,(H2,28,29,30,32)/t17-,18+
comment: AZD4547 was a fibroblast growth factor receptor (FGFR) tyrosine kinase family inhibitor, investigated as a potential treatment for solid tumours. This compound is now included in AstaZeneca's Open Innovation Pharmacology Toolbox.
iupac name: N-[5-[2-(3,5-dimethoxyphenyl)ethyl]-1H-pyrazol-3-yl]-4-[(3R,5S)-3,5-dimethylpiperazin-1-yl]benzamide
synonym: AZD-4547
synonym: KB-74810
approved: f
ligand name: AZD4547
type: SyntheticOrganicLigand

AZD3463
in ch i key: GCYIGMXOIWJGBU-UHFFFAOYSA-N
in ch i: InChI=1S/C24H25ClN6O/c1-32-22-12-16(31-10-8-15(26)9-11-31)6-7-21(22)29-24-28-14-19(25)23(30-24)18-13-27-20-5-3-2-4-17(18)20/h2-7,12-15,27H,8-11,26H2,1H3,(H,28,29,30)
comment: AZD3463 was investigated as a treatement for non-small cell lung cancer (NSCLC) patients who have developed resistance to <Ligand id=4903/>. AZD3463 inhibits the tyrosine kinases ALK and IGF1R. This compound is included in AstaZeneca's Open Innovation Pharmacology Toolbox.
iupac name: N-[4-(4-aminopiperidin-1-yl)-2-methoxyphenyl]-5-chloro-4-(1H-indol-3-yl)pyrimidin-2-amine
synonym: AZD-3463
synonym: CS-1382
synonym: HY-15609
synonym: KB-154896
approved: f
ligand name: AZD3463
type: SyntheticOrganicLigand

lesogaberan
canonical SMILES: NCC(CP(=O)O)F
isomeric SMILES: NC[C@H](CP(=O)O)F
in ch i key: LJNUIEQATDYXJH-GSVOUGTGSA-N
in ch i: InChI=1S/C3H9FNO2P/c4-3(1-5)2-8(6)7/h3,8H,1-2,5H2,(H,6,7)/t3-/m1/s1
comment: Lesogaberan is an agonist of gamma-aminobutyric acid receptor B (GABAB). This was an investigational compound tested for potential to treat gastroesophageal reflux disease (GERD). This compound is now included in AstaZeneca's Open Innovation Pharmacology Toolbox.
iupac name: [(2R)-3-amino-2-fluoropropyl]phosphinic acid
xref: CHEMBL448343
synonym: AZD-3355
synonym: AZD3355
approved: f
ligand name: lesogaberan
type: SyntheticOrganicLigand

AZD2927
in ch i key: GAHPWXLXWUVMIV-MRXNPFEDSA-N
in ch i: InChI=1S/C17H25FN2O2/c1-11(2)16(10-20-8-14(21)9-20)19(4)17(22)13-5-6-15(18)12(3)7-13/h5-7,11,14,16,21H,8-10H2,1-4H3/t16-/m1/s1
comment: AZD2927 blocks the potassium channels Kir3.1/Kir3.4 which convey an inwardly rectifying potassium current (IKACh). AZD2927 was used as an investigative compound as a potential treatment for patients with atrial flutter, but efficacy was not shown. This compound is now included in AstaZeneca's Open Innovation Pharmacology Toolbox.
iupac name: 4-fluoro-N-[(2S)-1-(3-hydroxyazetidin-1-yl)-3-methylbutan-2-yl]-N,3-dimethylbenzamide
synonym: AZD-2927
synonym: AZD 2927
approved: f
ligand name: AZD2927
type: SyntheticOrganicLigand

SRT1720
in ch i key: IASPBORHOMBZMY-UHFFFAOYSA-N
in ch i: InChI=1S/C25H23N7OS/c33-24(22-13-27-20-7-3-4-8-21(20)28-22)29-19-6-2-1-5-18(19)23-15-32-17(16-34-25(32)30-23)14-31-11-9-26-10-12-31/h1-8,13,15-16,26H,9-12,14H2,(H,29,33)
comment: SRT1720 is a selective SIRT1 activator. SRT1720 binds to the SIRT1 enzyme–peptide substrate complex at an allosteric site amino-terminal to the catalytic domain <Reference id=25399/>. In vivo studies show that SIRT1 activation has the potential to improve insulin sensitivity in animal models of obesity, and improve glucose homeostasis <Reference id=25399/>. This indicates the potential of such compounds as treatment for type II diabetes.
iupac name: N-[2-[3-(piperazin-1-ylmethyl)imidazo[2,1-b][1,3]thiazol-6-yl]phenyl]quinoxaline-2-carboxamide
xref: CHEMBL257991
approved: f
ligand name: SRT1720
type: SyntheticOrganicLigand

adavosertib
in ch i key: BKWJAKQVGHWELA-UHFFFAOYSA-N
in ch i: InChI=1S/C27H32N8O2/c1-5-13-34-25(36)21-18-28-26(29-19-9-11-20(12-10-19)33-16-14-32(4)15-17-33)31-24(21)35(34)23-8-6-7-22(30-23)27(2,3)37/h5-12,18,37H,1,13-17H2,2-4H3,(H,28,29,31)
comment: Adavosertib (AZD1775) inhibits WEE1 G2 checkpoint kinase. It was developed as a potential adjunctive therapeutic for advanced solid tumours. This compound is included in AstaZeneca's Open Innovation Pharmacology Toolbox.
iupac name: 1-[6-(2-hydroxypropan-2-yl)pyridin-2-yl]-6-[4-(4-methylpiperazin-1-yl)anilino]-2-prop-2-enylpyrazolo[3,4-d]pyrimidin-3-one
xref: CHEMBL1976040
synonym: MK-1775
synonym: MK1775
synonym: AZD1775
synonym: AZD 1775
synonym: AZD-1775
approved: f
ligand name: adavosertib
type: SyntheticOrganicLigand

AZD1332
in ch i key: LBVKEEFIPBQIMD-UHFFFAOYSA-N
in ch i: InChI=1S/C17H19ClFN7O/c1-9(2)27-15-6-14(25-26-15)23-16-12(18)8-21-17(24-16)22-10(3)13-5-4-11(19)7-20-13/h4-10H,1-3H3,(H3,21,22,23,24,25,26)
comment: AZD1332 is an inhibitor of neurotrophic tyrosine kinase receptors trkA, B and C (aka neurotrophic tyrosine kinase, receptor, type 1, 2 and 3). This compound is included in AstaZeneca's Open Innovation Pharmacology Toolbox.
iupac name: 5-chloro-2-N-[1-(5-fluoropyridin-2-yl)ethyl]-4-N-(3-propan-2-yloxy-1H-pyrazol-5-yl)pyrimidine-2,4-diamine
xref: CHEMBL2007421
synonym: AZD 1332
synonym: AZD-1332
approved: f
ligand name: AZD1332
type: SyntheticOrganicLigand

vistusertib
in ch i key: JUSFANSTBFGBAF-IRXDYDNUSA-N
in ch i: InChI=1S/C25H30N6O3/c1-16-14-33-11-9-30(16)23-20-7-8-21(18-5-4-6-19(13-18)24(32)26-3)27-22(20)28-25(29-23)31-10-12-34-15-17(31)2/h4-8,13,16-17H,9-12,14-15H2,1-3H3,(H,26,32)/t16-,17-/m0/s1
comment: Vistusertib (AZD2014) is a selective inhibitor of Mammalian target of rapamycin (mTOR) serine/ threonine kinase. This compound is included in AstaZeneca's Open Innovation Pharmacology Toolbox.
iupac name: 3-[2,4-bis[(3S)-3-methylmorpholin-4-yl]pyrido[2,3-d]pyrimidin-7-yl]-N-methylbenzamide
xref: CHEMBL2336325
synonym: AZD-2014
synonym: cc-551
synonym: AZD 2014
synonym: AZD2014
approved: f
ligand name: vistusertib
type: SyntheticOrganicLigand

AZD1208
in ch i key: MCUJKPPARUPFJM-UWCCDQBKSA-N
in ch i: InChI=1S/C21H21N3O2S/c22-16-9-5-11-24(13-16)19-15(12-18-20(25)23-21(26)27-18)8-4-10-17(19)14-6-2-1-3-7-14/h1-4,6-8,10,12,16H,5,9,11,13,22H2,(H,23,25,26)/b18-12-/t16-/m1/s1
comment: AZD1208 inhibits all members of the proviral integration Moloney virus (PIM) serine/threonine kinase family, that was intended for use as an anticancer drug <Reference id=25395/><Reference id=37602/>. This compound is included in AstaZeneca's Open Innovation Pharmacology Toolbox.
iupac name: (5Z)-5-[[2-[(3R)-3-aminopiperidin-1-yl]-3-phenylphenyl]methylidene]-1,3-thiazolidine-2,4-dione
xref: CHEMBL2048872
synonym: AZD-1208
synonym: AZD 1208
approved: f
ligand name: AZD1208
type: SyntheticOrganicLigand

VU591
in ch i key: ZQPXNYLXYNRFNP-UHFFFAOYSA-N
in ch i: InChI=1S/C16H12N6O5/c23-21(24)9-1-3-11-13(5-9)19-15(17-11)7-27-8-16-18-12-4-2-10(22(25)26)6-14(12)20-16/h1-6H,7-8H2,(H,17,19)(H,18,20)
iupac name: 6-nitro-2-[(6-nitro-1H-benzimidazol-2-yl)methoxymethyl]-1H-benzimidazole
xref: CHEMBL2146753
synonym: VU 591
synonym: VU-591
approved: f
ligand name: VU591
type: SyntheticOrganicLigand

AZD4017
in ch i key: NCDZABJPWMBMIQ-INIZCTEOSA-N
in ch i: InChI=1S/C22H33N3O3S/c1-2-13-29-22-18(21(28)23-17-8-4-3-5-9-17)10-11-19(24-22)25-12-6-7-16(15-25)14-20(26)27/h10-11,16-17H,2-9,12-15H2,1H3,(H,23,28)(H,26,27)/t16-/m0/s1
comment: AZD4017 is a selective inhibitor of 11-beta-hydroxysteroid dehydrogenase type 1 (11β-HSD1) <Reference id=25358/><Reference id=25359/>. This compound is listed in AstraZeneca's OpenInnovation Pharmacology Toolbox .
iupac name: 2-[(3S)-1-[5-(cyclohexylcarbamoyl)-6-propylsulfanylpyridin-2-yl]piperidin-3-yl]acetic acid
xref: CHEMBL2153191
synonym: AZD-4017
synonym: AZD 4017
approved: f
ligand name: AZD4017
type: SyntheticOrganicLigand

SB269652
in ch i key: JGLGOAQPUQITLD-OGAOHHHESA-N
in ch i: InChI=1S/C27H30N4O/c28-17-20-5-8-21-12-14-31(18-23(21)15-20)13-11-19-6-9-24(10-7-19)29-27(32)26-16-22-3-1-2-4-25(22)30-26/h1-5,8,15-16,19,24,30H,6-7,9-14,18H2,(H,29,32)/t19-,24-
comment: SB269652 was originally described as an allosteric antagonist at dopamine D3 and D2 receptors <Reference id=25339/>. Further analysis has revealed a novel mechanism of allostery, which relies on the presence of receptor dimers <Reference id=25338/>. SB269652 acts as a bitopic ligand <Reference id=25340/>, with one pharmacophore binding to one receptor protomer and the other pharmacophore allosterically modulating the binding of a ligand on the second partner in the dimer, in this instance rendering the compound a negative allosteric regulator of dopamine binding to the D2 receptor <Reference id=25338/>. PubChem CID 9910352 represents the compound structure without specified stereochemistry.
iupac name: N-[(1r,4r)-4-[2-(7-cyano-1,2,3,4-tetrahydroisoquinolin-2-yl)ethyl]cyclohexyl]-1H-indole-2-carboxamide
xref: CHEMBL2219578
synonym: SB-269,652
synonym: SB-269652
approved: f
ligand name: SB269652
type: SyntheticOrganicLigand

eluxadoline
in ch i key: QFNHIDANIVGXPE-FNZWTVRRSA-N
in ch i: InChI=1S/C32H35N5O5/c1-18-12-23(29(34)38)13-19(2)24(18)15-26(33)31(39)37(17-21-10-11-28(42-4)25(14-21)32(40)41)20(3)30-35-16-27(36-30)22-8-6-5-7-9-22/h5-14,16,20,26H,15,17,33H2,1-4H3,(H2,34,38)(H,35,36)(H,40,41)/t20-,26-/m0/s1
comment: Eluxadoline is a first-in-class, locally-acting dual μ-opioid receptor agonist and δ-opioid receptor antagonist <Reference id=25330/><Reference id=25331/>.
iupac name: 5-[[[(2S)-2-amino-3-(4-carbamoyl-2,6-dimethylphenyl)propanoyl]-[(1S)-1-(4-phenyl-3H-imidazol-2-yl)ethyl]amino]methyl]-2-methoxybenzoic acid
xref: CHEMBL2159122
synonym: JNJ-27018966
synonym: Truberzi®
approved: t
ligand name: eluxadoline
type: SyntheticOrganicLigand

AR-H067637
in ch i key: QTUUCFVBSVJGOH-DLBZAZTESA-N
comment: AR-H067637 is the major active metabolite of atecegatran metoxil <Reference id=25293/>. PubChem have the non-chiral version of this compound listed with CID 10298659.
iupac name: (2S)-N-[(4-carbamimidoylphenyl)methyl]-1-[(2R)-2-[3-chloro-5-(difluoromethoxy)phenyl]-2-hydroxyacetyl]azetidine-2-carboxamide
approved: f
ligand name: AR-H067637
type: SyntheticOrganicLigand

AZD6703
in ch i key: ZMAZXHICVRYLQN-UHFFFAOYSA-N
in ch i: InChI=1S/C24H27N5O2/c1-16-3-4-17(23(30)26-18-5-6-18)13-22(16)29-15-25-21-8-7-19(14-20(21)24(29)31)28-11-9-27(2)10-12-28/h3-4,7-8,13-15,18H,5-6,9-12H2,1-2H3,(H,26,30)
comment: AZD6703 is a potent, selective and reversible orally bioavailable inhibitor of p38 mitogen-activated protein kinase 14 (MAPK14). This compound was in the AstraZeneca/MRC repurposing list from 2011.
iupac name: N-cyclopropyl-4-methyl-3-[6-(4-methylpiperazin-1-yl)-4-oxoquinazolin-3-yl]benzamide
xref: CHEMBL2031465
synonym: AZD 6703
synonym: AZD-6703
synonym: AZ12012199
synonym: AZ 12012199
synonym: AZ-12012199
approved: f
ligand name: AZD6703
type: SyntheticOrganicLigand

AZD5672
in ch i key: QOSMEMHKXNNIGG-SSEXGKCCSA-N
comment: AZD5672 was an investigational small molecule antagonist of the C-C chemokine receptor type 5 (CCR5) expressed on T cells. AZD5672-induced CCR5 blockade was investigated for action in treating rheumatoid arthritis, but with discouraging clinical trial results. Other CCR5 antagonists (<Ligand id=804/> and <Ligand id=806/>) have also proven ineffective in RA clinical trials <Reference id=30655/> The structure shown here was drawn from <Reference id=25287/>.
iupac name: N-[1-[(3R)-3-(3,5-difluorophenyl)-3-(1-methylsulfonylpiperidin-4-yl)propyl]piperidin-4-yl]-N-ethyl-2-(4-methylsulfonylphenyl)acetamide
xref: CHEMBL1951914
synonym: AZD 5672
synonym: AZD-5672
approved: f
ligand name: AZD5672
type: SyntheticOrganicLigand

PF-592379
canonical SMILES: CCCN1CC(OCC1C)c1ccc(nc1)N
isomeric SMILES: CCCN1C[C@H](OC[C@@H]1C)c1ccc(nc1)N
in ch i key: DFTCYTDJDXZFSK-JQWIXIFHSA-N
in ch i: InChI=1S/C13H21N3O/c1-3-6-16-8-12(17-9-10(16)2)11-4-5-13(14)15-7-11/h4-5,7,10,12H,3,6,8-9H2,1-2H3,(H2,14,15)/t10-,12-/m0/s1
comment: PF-592379 was investigated as a potential treatment for female sexual dysfunction and male erectile dysfunction.
iupac name: 5-[(2R,5S)-5-methyl-4-propylmorpholin-2-yl]pyridin-2-amine
synonym: PF-592,379
approved: f
ligand name: PF-592379
type: SyntheticOrganicLigand

atecegatran metoxil
in ch i key: XSNMGLZVFNDDPW-ZWKOTPCHSA-N
comment: This direct thrombin inhibitor prodrug (aka AZD0837) from AstraZeneca was the follow-up for <Ligand id=7804/>. It is dicussed in the recent AZ 2014 review paper <Reference id=26127/>.
synonym: AZD0837
synonym: AZD-0837
synonym: AZD 0837
synonym: atecegatran fexenetil
approved: f
ligand name: atecegatran metoxil
type: SyntheticOrganicLigand

lanicemine
canonical SMILES: NC(c1ccccc1)Cc1ccccn1
isomeric SMILES: N[C@H](c1ccccc1)Cc1ccccn1
in ch i key: FWUQWDCOOWEXRY-ZDUSSCGKSA-N
in ch i: InChI=1S/C13H14N2/c14-13(11-6-2-1-3-7-11)10-12-8-4-5-9-15-12/h1-9,13H,10,14H2/t13-/m0/s1
comment: Lanicemine (AZD 6765) was originally developed as a neuroprotective agent, but was repurposed as an antidepressant with potential for the management of severe and treatment-resistant depression <Reference id=25295/>. However, the compound failed to meet study endpoints, so development was halted. The compound is discussed in the AZ 2014 review paper <Reference id=26127/>. The structure represented here shows stereochemistry identical to the INN record wheras PubChem CID 3038485 represents the non-chiral molecule.
iupac name: (1S)-1-phenyl-2-pyridin-2-ylethanamine
xref: CHEMBL467084
synonym: AZD6765
synonym: AZD-6765
synonym: AR-R15896AR
synonym: ARL 15896
approved: f
ligand name: lanicemine
type: SyntheticOrganicLigand

AZD1981
in ch i key: JWYIGNODXSRKGP-UHFFFAOYSA-N
comment: AZD1981 was an investigational compound being assessed as a potential treatment for asthma. Mechanistically it is a potent, orally active, selective and reversible antagonist of the DP2 receptor (CRTH2). This compound is now included for repurposing in the AstaZeneca's Open Innovation Pharmacology Toolbox. It was also Case Study (2) in the AZ 2014 review paper <Reference id=26127/>.
iupac name: 2-[4-acetamido-3-(4-chlorophenyl)sulfanyl-2-methylindol-1-yl]acetic acid
xref: CHEMBL1914489
synonym: AZD-1981
synonym: AZD 1981
approved: f
ligand name: AZD1981
type: SyntheticOrganicLigand

genistein
canonical SMILES: Oc1ccc(cc1)c1coc2c(c1=O)c(O)cc(c2)O
isomeric SMILES: Oc1ccc(cc1)c1coc2c(c1=O)c(O)cc(c2)O
in ch i key: TZBJGXHYKVUXJN-UHFFFAOYSA-N
in ch i: InChI=1S/C15H10O5/c16-9-3-1-8(2-4-9)11-7-20-13-6-10(17)5-12(18)14(13)15(11)19/h1-7,16-18H
iupac name: 5,7-dihydroxy-3-(4-hydroxyphenyl)chromen-4-one
xref: CHEMBL44
synonym: 5,7,4'-trihydroxyisoflavone
approved: f
ligand name: genistein
type: SyntheticOrganicLigand

AZD3778
in ch i key: QVLZVRFIGXNZMN-UHFFFAOYSA-N
comment: AZD3778 was an investigational chemokine receptor antagonist, being evaluated as a potentila treatment for asthma. However, the compound failed to show efficacy and development project was halted. A poor level of target engagement and sub-optimal pharmacodynamic activity due to the pharmacokinetic properties of the compound were likely causes. This compound is discussed in the AZ 2014 review paper <Reference id=26127/>.
iupac name: 4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]-N-(4-methylphenyl)sulfonylpiperidine-1-carboxamide
xref: CHEMBL2158814
synonym: AZD 3778
synonym: AZD-3778
approved: f
ligand name: AZD3778
type: SyntheticOrganicLigand

AZD8529
in ch i key: IPCYZQQFECEHLI-UHFFFAOYSA-N
in ch i: InChI=1S/C24H24F3N5O3/c1-15-10-17(22-29-20(30-35-22)14-31-8-6-28-7-9-31)11-18-13-32(23(33)21(15)18)12-16-2-4-19(5-3-16)34-24(25,26)27/h2-5,10-11,28H,6-9,12-14H2,1H3
comment: AZD8529 is a metabotropic glutamate receptor 2 (mGluR2) positive allosteric modulator. Since the original schizophrenia indication is not being pursued it is offered for clinical and preclinical research to explore novel biology with a view to repurposing (it was also in the 2012 NCATS set). Discussed as Case Study (1) in the AZ 2014 review paper <Reference id=26127/>.
iupac name: 7-methyl-5-[3-(piperazin-1-ylmethyl)-1,2,4-oxadiazol-5-yl]-2-[[4-(trifluoromethoxy)phenyl]methyl]-3H-isoindol-1-one
synonym: AZD-8529
synonym: AZD 8529
approved: f
ligand name: AZD8529
type: SyntheticOrganicLigand

PD-307243
in ch i key: WNXIPCSWXVTKQF-UHFFFAOYSA-N
iupac name: 2-[[2-(3,4-dichlorophenyl)-1,3-dihydroisoindol-5-yl]amino]pyridine-3-carboxylic acid
synonym: PD307243
synonym: PD 307243
approved: f
ligand name: PD-307243
type: SyntheticOrganicLigand

[3H]histidine
canonical SMILES: NC(C(=O)O)Cc1c[nH]cn1
isomeric SMILES: N[C@H](C(=O)O)Cc1c[nH]cn1
in ch i key: HNDVDQJCIGZPNO-YFKPBYRVSA-N
in ch i: InChI=1S/C6H9N3O2/c7-5(6(10)11)1-4-2-8-3-9-4/h2-3,5H,1,7H2,(H,8,9)(H,10,11)/t5-/m0/s1
iupac name: (2S)-2-amino-3-(1H-imidazol-4-yl)propanoic acid
xref: CHEMBL17962
synonym: [3H]-histidine
approved: f
ligand name: [3H]histidine
type: SyntheticOrganicLigand

PD-118057
in ch i key: ZCQOSCDABPVAFB-UHFFFAOYSA-N
in ch i: InChI=1S/C21H17Cl2NO2/c22-18-12-9-15(13-19(18)23)6-5-14-7-10-16(11-8-14)24-20-4-2-1-3-17(20)21(25)26/h1-4,7-13,24H,5-6H2,(H,25,26)
iupac name: 2-[[4-[2-(3,4-dichlorophenyl)ethyl]phenyl]amino]benzoic acid
xref: CHEMBL521083
synonym: PD118057
synonym: PD 118057
approved: f
ligand name: PD-118057
type: SyntheticOrganicLigand

lesinurad
in ch i key: FGQFOYHRJSUHMR-UHFFFAOYSA-N
comment: Lesinurad is an orally available inhibitor of URAT1, the renal transporter that regulates uric acid excretion from the body <Reference id=25272/><Reference id=25273/>.
iupac name: 2-[[5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-1,2,4-triazol-3-yl]sulfanyl]acetic acid
xref: CHEMBL2105720
synonym: RDEA594
synonym: RDEA-594
synonym: Zurampic®
approved: t
ligand name: lesinurad
type: SyntheticOrganicLigand

brexpiprazole
in ch i key: ZKIAIYBUSXZPLP-UHFFFAOYSA-N
in ch i: InChI=1S/C25H27N3O2S/c29-25-9-7-19-6-8-20(18-22(19)26-25)30-16-2-1-11-27-12-14-28(15-13-27)23-4-3-5-24-21(23)10-17-31-24/h3-10,17-18H,1-2,11-16H2,(H,26,29)
comment: Brexpiprazole is a serotonin-dopamine activity modulator (SDAM) <Reference id=25271/>.
iupac name: 7-[4-[4-(1-benzothiophen-4-yl)piperazin-1-yl]butoxy]-1H-quinolin-2-one
xref: CHEMBL2105760
synonym: OPC 34712
synonym: OPC-34712
synonym: Rxulti®
approved: t
ligand name: brexpiprazole
type: SyntheticOrganicLigand

cariprazine
in ch i key: KPWSJANDNDDRMB-QAQDUYKDSA-N
in ch i: InChI=1S/C21H32Cl2N4O/c1-25(2)21(28)24-17-8-6-16(7-9-17)10-11-26-12-14-27(15-13-26)19-5-3-4-18(22)20(19)23/h3-5,16-17H,6-15H2,1-2H3,(H,24,28)/t16-,17-
comment: Cariprazine is an antipsychotic. Our structure was drawn from the INN record which shows stereo-chemistry for this compound. PubChem have a record only for the non-chiral molecule, with CID 11154555. The compound is liphophilic meaning that it can easily cross the blood-brain barrier, to reach its site of action <Reference id=25270/>.
iupac name: 3-[4-[2-[4-(2,3-dichlorophenyl)piperazin-1-yl]ethyl]cyclohexyl]-1,1-dimethylurea
xref: CHEMBL2028019
synonym: RGH 188
synonym: RGH-188
synonym: Reagila®
synonym: Vraylar®
approved: t
ligand name: cariprazine
type: SyntheticOrganicLigand

blonanserin
in ch i key: XVGOZDAJGBALKS-UHFFFAOYSA-N
in ch i: InChI=1S/C23H30FN3/c1-2-26-13-15-27(16-14-26)23-17-21(18-9-11-19(24)12-10-18)20-7-5-3-4-6-8-22(20)25-23/h9-12,17H,2-8,13-16H2,1H3
comment: Blonanserin is an atypical antipsychotic.
iupac name: 2-(4-ethylpiperazin-1-yl)-4-(4-fluorophenyl)-5,6,7,8,9,10-hexahydrocycloocta[b]pyridine
xref: CHEMBL178803
synonym: Lonasen®
synonym: AD 5423
synonym: AD-5423
approved: t
ligand name: blonanserin
type: SyntheticOrganicLigand

QO-58
in ch i key: JEXACLGXUUYXDX-UHFFFAOYSA-N
comment: PubChem CID 51351551 represents an alternative isomer of this compound.
iupac name: 5-(2,6-dichloro-5-fluoropyridin-3-yl)-3-phenyl-2-(trifluoromethyl)-1H-pyrazolo[1,5-a]pyrimidin-7-one
xref: CHEMBL1689654
approved: f
ligand name: QO-58
type: SyntheticOrganicLigand

ztz240
canonical SMILES: Fc1ccc(cc1)C(=O)Nc1ccc(nc1)Cl
isomeric SMILES: Fc1ccc(cc1)C(=O)Nc1ccc(nc1)Cl
in ch i key: URPKVELJRWKNQS-UHFFFAOYSA-N
in ch i: InChI=1S/C12H8ClFN2O/c13-11-6-5-10(7-15-11)16-12(17)8-1-3-9(14)4-2-8/h1-7H,(H,16,17)
iupac name: N-(6-chloropyridin-3-yl)-4-fluorobenzamide
xref: CHEMBL1454208
approved: f
ligand name: ztz240
type: SyntheticOrganicLigand

ICA-27243
canonical SMILES: Clc1ccc(cn1)NC(=O)c1ccc(c(c1)F)F
isomeric SMILES: Clc1ccc(cn1)NC(=O)c1ccc(c(c1)F)F
in ch i key: GDGUOCFTHNGPBK-UHFFFAOYSA-N
in ch i: InChI=1S/C12H7ClF2N2O/c13-11-4-2-8(6-16-11)17-12(18)7-1-3-9(14)10(15)5-7/h1-6H,(H,17,18)
iupac name: N-(6-chloropyridin-3-yl)-3,4-difluorobenzamide
xref: CHEMBL402146
synonym: ICA 27243
synonym: ICA27243
approved: f
ligand name: ICA-27243
type: SyntheticOrganicLigand

ML277
in ch i key: OXQNLLVUVDAEHC-OAQYLSRUSA-N
in ch i: InChI=1S/C23H25N3O4S2/c1-16-6-12-19(13-7-16)32(28,29)26-14-4-3-5-21(26)22(27)25-23-24-20(15-31-23)17-8-10-18(30-2)11-9-17/h6-13,15,21H,3-5,14H2,1-2H3,(H,24,25,27)/t21-/m1/s1
iupac name: (2R)-N-[4-(4-methoxyphenyl)-1,3-thiazol-2-yl]-1-(4-methylphenyl)sulfonylpiperidine-2-carboxamide
xref: CHEMBL2070953
synonym: ML-277
synonym: ML 277
approved: f
ligand name: ML277
type: SyntheticOrganicLigand

ML213
canonical SMILES: O=C(C1CC2CC1CC2)Nc1c(C)cc(cc1C)C
isomeric SMILES: O=C(C1CC2CC1CC2)Nc1c(C)cc(cc1C)C
in ch i key: SIQGKPGBLYKQBB-UHFFFAOYSA-N
in ch i: InChI=1S/C17H23NO/c1-10-6-11(2)16(12(3)7-10)18-17(19)15-9-13-4-5-14(15)8-13/h6-7,13-15H,4-5,8-9H2,1-3H3,(H,18,19)
iupac name: N-(2,4,6-trimethylphenyl)bicyclo[2.2.1]heptane-6-carboxamide
xref: CHEMBL1703636
synonym: ML 213
synonym: ML-213
approved: f
ligand name: ML213
type: SyntheticOrganicLigand

NC00075159
isomeric SMILES: CC(N1C(=S)S/C(=C/c2ccc(cc2)N(C)C)/C1=O)C(=O)O
in ch i key: XGTGMKYGVNHPTC-WQLSENKSSA-N
in ch i: InChI=1S/C15H16N2O3S2/c1-9(14(19)20)17-13(18)12(22-15(17)21)8-10-4-6-11(7-5-10)16(2)3/h4-9H,1-3H3,(H,19,20)/b12-8-
iupac name: 2-[5-[(4-dimethylaminophenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]propanoic acid
approved: f
ligand name: NC00075159
type: SyntheticOrganicLigand

CX4
in ch i key: LHTLPGOZLLOCIS-UHFFFAOYSA-N
in ch i: InChI=1S/C22H21ClN2S/c1-16-9-8-14-19(23)21(16)25-22(26)24-20(18-12-6-3-7-13-18)15-17-10-4-2-5-11-17/h2-14,20H,15H2,1H3,(H2,24,25,26)
iupac name: 3-(2-chloro-6-methylphenyl)-1-[1,2-di(phenyl)ethyl]thiourea
approved: f
ligand name: CX4
type: SyntheticOrganicLigand

VU0405601
canonical SMILES: O=C(Nc1cccnc1)COc1ccc2c(c1Br)cccc2
isomeric SMILES: O=C(Nc1cccnc1)COc1ccc2c(c1Br)cccc2
in ch i key: WLLRAGBPCSOJNH-UHFFFAOYSA-N
in ch i: InChI=1S/C17H13BrN2O2/c18-17-14-6-2-1-4-12(14)7-8-15(17)22-11-16(21)20-13-5-3-9-19-10-13/h1-10H,11H2,(H,20,21)
iupac name: 2-(1-bromonaphthalen-2-yl)oxy-N-pyridin-3-ylacetamide
xref: CHEMBL1418045
synonym: VU 0405601
synonym: VU-0405601
approved: f
ligand name: VU0405601
type: SyntheticOrganicLigand

A-935142
in ch i key: YPHFQSYEKIEMNC-HAQNSBGRSA-N
in ch i: InChI=1S/C18H19F3N2O2/c19-18(20,21)16-10-15(22-23-16)14-7-5-13(6-8-14)12-3-1-11(2-4-12)9-17(24)25/h5-8,10-12H,1-4,9H2,(H,22,23)(H,24,25)/t11-,12-
iupac name: 2-[4-[4-[5-(trifluoromethyl)-1H-pyrazol-3-yl]phenyl]cyclohexyl]acetic acid
synonym: A935142
synonym: A 935142
approved: f
ligand name: A-935142
type: SyntheticOrganicLigand

dosulepin
canonical SMILES: CN(CCC=C1c2ccccc2SCc2c1cccc2)C
isomeric SMILES: CN(CC/C=C/1/c2ccccc2SCc2c1cccc2)C
in ch i key: PHTUQLWOUWZIMZ-BOPFTXTBSA-N
in ch i: InChI=1S/C19H21NS/c1-20(2)13-7-11-17-16-9-4-3-8-15(16)14-21-19-12-6-5-10-18(17)19/h3-6,8-12H,7,13-14H2,1-2H3/b17-11-
comment: Dosulepin is a tricyclic antidepressant. Functionally it acts as a serotonin-norepinephrine reuptake inhibitor (SNRI) with anticholinergic, antihistamine, and antiadrenergic effects.
iupac name: (3Z)-3-(6H-benzo[c][1]benzothiepin-11-ylidene)-N,N-dimethylpropan-1-amine
xref: CHEMBL108947
synonym: dothiepin
synonym: Dopress
synonym: Thaden
synonym: Prothiaden®
synonym: Dothep®
approved: t
ligand name: dosulepin
type: SyntheticOrganicLigand

NS3623
in ch i key: JXPULDIATMTIIN-UHFFFAOYSA-N
iupac name: 1-[4-bromo-2-(2H-tetrazol-5-yl)phenyl]-3-[3-(trifluoromethyl)phenyl]urea
synonym: NS 3623
synonym: NS-3623
approved: f
ligand name: NS3623
type: SyntheticOrganicLigand

KB-130015
canonical SMILES: OC(=O)COc1c(I)cc(cc1I)Cc1c(C)oc2c1cccc2
isomeric SMILES: OC(=O)COc1c(I)cc(cc1I)Cc1c(C)oc2c1cccc2
in ch i key: OLIKCJUMYWSDIV-UHFFFAOYSA-N
in ch i: InChI=1S/C18H14I2O4/c1-10-13(12-4-2-3-5-16(12)24-10)6-11-7-14(19)18(15(20)8-11)23-9-17(21)22/h2-5,7-8H,6,9H2,1H3,(H,21,22)
iupac name: 2-[2,6-diiodo-4-[(2-methyl-1-benzofuran-3-yl)methyl]phenoxy]acetic acid
xref: CHEMBL157885
synonym: KB 130015
synonym: KB130015
approved: f
ligand name: KB-130015
type: SyntheticOrganicLigand

pelitinib
isomeric SMILES: CCOc1cc2ncc(c(c2cc1NC(=O)/C=C/CN(C)C)Nc1ccc(c(c1)Cl)F)C#N
in ch i key: WVUNYSQLFKLYNI-AATRIKPKSA-N
comment: Pelitinib is an irreversible inhibitor of EGFR and HER2.
iupac name: (E)-N-[4-[(3-chloro-4-fluorophenyl)amino]-3-cyano-7-ethoxyquinolin-6-yl]-4-dimethylaminobut-2-enamide
xref: CHEMBL607707
synonym: EKB-569
approved: f
ligand name: pelitinib
type: SyntheticOrganicLigand

ginsenoside Rg3
in ch i key: RWXIFXNRCLMQCD-JBVRGBGGSA-N
in ch i: InChI=1S/C42H72O13/c1-21(2)10-9-14-42(8,51)22-11-16-41(7)29(22)23(45)18-27-39(5)15-13-28(38(3,4)26(39)12-17-40(27,41)6)54-37-35(33(49)31(47)25(20-44)53-37)55-36-34(50)32(48)30(46)24(19-43)52-36/h10,22-37,43-51H,9,11-20H2,1-8H3/t22-,23+,24+,25+,26-,27+,28-,29-,30+,31+,32-,33-,34+,35+,36-,37-,39-,40+,41+,42-/m0/s1
iupac name: (2S,3R,4S,5S,6R)-2-[(2R,3R,4S,5S,6R)-4,5-dihydroxy-2-[[(3S,5R,8R,9R,10R,12R,13R,14R,17S)-12-hydroxy-17-[(2S)-2-hydroxy-6-methylhept-5-en-2-yl]-4,4,8,10,14-pentamethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-6-(hydroxymethyl)oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
xref: CHEMBL398412
synonym: (20S)-ginsenoside Rg3
approved: f
ligand name: ginsenoside Rg3
type: NaturalProductLigand

RPR260243
in ch i key: VWNMWKSURFWKAL-HXOBKFHXSA-N
in ch i: InChI=1S/C28H25F3N2O4/c1-37-20-5-6-25-22(15-20)21(8-10-32-25)26(34)7-4-17-9-12-33(16-23(17)28(35)36)11-2-3-18-13-19(29)14-24(30)27(18)31/h5-6,8,10,13-15,17,23H,4,7,9,11-12,16H2,1H3,(H,35,36)/t17-,23+/m1/s1
iupac name: (3R,4R)-4-[3-(6-methoxyquinolin-4-yl)-3-oxopropyl]-1-[3-(2,3,5-trifluorophenyl)prop-2-ynyl]piperidine-3-carboxylic acid
xref: CHEMBL406931
synonym: RPR-260243
synonym: RPR 260243
approved: f
ligand name: RPR260243
type: SyntheticOrganicLigand

ICA-105574
canonical SMILES: O=C(c1cccc(c1)[N+](=O)[O-])Nc1ccc(cc1)Oc1ccccc1
isomeric SMILES: O=C(c1cccc(c1)[N+](=O)[O-])Nc1ccc(cc1)Oc1ccccc1
in ch i key: GDWKBKTVROCPNZ-UHFFFAOYSA-N
in ch i: InChI=1S/C19H14N2O4/c22-19(14-5-4-6-16(13-14)21(23)24)20-15-9-11-18(12-10-15)25-17-7-2-1-3-8-17/h1-13H,(H,20,22)
iupac name: 3-nitro-N-[4-(phenoxy)phenyl]benzamide
synonym: ICA 105574
synonym: ICA105574
approved: f
ligand name: ICA-105574
type: SyntheticOrganicLigand

estradiol valerate
in ch i key: RSEPBGGWRJCQGY-RBRWEJTLSA-N
in ch i: InChI=1S/C23H32O3/c1-3-4-5-22(25)26-21-11-10-20-19-8-6-15-14-16(24)7-9-17(15)18(19)12-13-23(20,21)2/h7,9,14,18-21,24H,3-6,8,10-13H2,1-2H3/t18-,19-,20+,21+,23+/m1/s1
comment: Estradiol valerate is a synthetic ester of the endogenous estrogen, <Ligand id=1013/>. This ester is absorbed more slowly and has a longer duration of action than the native hormone. Estradiol valerate is cleaved in vivo by plasma and liver esterases to form 17β-estradiol and valeric acid.
iupac name: [(8R,9S,13S,14S,17S)-3-hydroxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl] pentanoate
xref: CHEMBL1511
synonym: Climaval®
approved: t
ligand name: estradiol valerate
type: SyntheticOrganicLigand

dienogest
canonical SMILES: N#CCC1(O)CCC2C1(C)CCC1=C3CCC(=O)C=C3CCC21
in ch i key: AZFLJNIPTRTECV-FUMNGEBKSA-N
in ch i: InChI=1S/C20H25NO2/c1-19-8-6-16-15-5-3-14(22)12-13(15)2-4-17(16)18(19)7-9-20(19,23)10-11-21/h12,17-18,23H,2-10H2,1H3/t17-,18+,19+,20-/m1/s1
comment: Note that the 2010 FDA approval is for the fixed-mixture combination oral contraceptive detailed in the Clinical data tab.
iupac name: 2-[(8S,13S,14S,17R)-17-hydroxy-13-methyl-3-oxo-1,2,6,7,8,11,12,14,15,16-decahydrocyclopenta[a]phenanthren-17-yl]acetonitrile
xref: CHEMBL1201864
synonym: STS-557
synonym: dienogestrel
approved: t
ligand name: dienogest
type: SyntheticOrganicLigand

ioflupane
canonical SMILES: FCCCN1C2CCC1C(C(C2)c1ccc(cc1)I)C(=O)OC
in ch i key: HXWLAJVUJSVENX-HFIFKADTSA-N
in ch i: InChI=1S/C18H23FINO2/c1-23-18(22)17-15(12-3-5-13(20)6-4-12)11-14-7-8-16(17)21(14)10-2-9-19/h3-6,14-17H,2,7-11H2,1H3/t14-,15+,16+,17-/m0/s1/i20-4
comment: This compound is represented on ChEMBL with slightly different stereochemistry by CHEMBL2096623.
iupac name: methyl (1S,3S,4S,5R)-8-(3-fluoropropyl)-3-(4-iodanylphenyl)-8-azabicyclo[3.2.1]octane-4-carboxylate
synonym: DaTSCAN®
synonym: 123I-ioflupane
synonym: 123I-FP-CIT
approved: t
ligand name: ioflupane
type: SyntheticOrganicLigand

UNC0006
in ch i key: NGCKUAWDNUFNBB-UHFFFAOYSA-N
comment: UNC0006 is an analog of <Ligand id=34/> and is a β-arrestin–biased dopamine D2 receptor ligand <Reference id=25195/>
iupac name: 7-{4-[4-(2,3-dichlorophenyl)-1,4-diazepan-1-yl]butoxy}-1,2,3,4-tetrahydroquinolin-2-one
xref: CHEMBL2165126
approved: f
ligand name: UNC0006
type: SyntheticOrganicLigand

UNC9975
in ch i key: JQSRFMXTGAVHIR-UHFFFAOYSA-N
comment: UNC9975 is an analog of <Ligand id=34/> and is a β-arrestin–biased dopamine D2 receptor ligand <Reference id=25195/>.
iupac name: 7-{4-[4-(2,3-dichlorophenyl)-1,4-diazepan-1-yl]butoxy}-1,2,3,4-tetrahydro-1,8-naphthyridin-2-one
xref: CHEMBL2165119
approved: f
ligand name: UNC9975
type: SyntheticOrganicLigand

lucitanib
in ch i key: CUDVHEFYRIWYQD-UHFFFAOYSA-N
in ch i: InChI=1S/C26H25N3O4/c1-28-25(30)19-5-3-4-16-12-17(6-7-18(16)19)33-22-8-11-29-21-14-24(23(31-2)13-20(21)22)32-15-26(27)9-10-26/h3-8,11-14H,9-10,15,27H2,1-2H3,(H,28,30)
comment: Lucitanib is an inhibitor of multiple receptor tyrosine kinases <Reference id=25193/> that was investigated for anti-angiogenic and anti-tumourigenic efficacy.
iupac name: 6-[7-[(1-aminocyclopropyl)methoxy]-6-methoxyquinolin-4-yl]oxy-N-methylnaphthalene-1-carboxamide
xref: CHEMBL2220486
synonym: E-3810 amine
synonym: E3810
approved: f
ligand name: lucitanib
type: SyntheticOrganicLigand

rivoceranib
in ch i key: WPEWQEMJFLWMLV-UHFFFAOYSA-N
in ch i: InChI=1S/C24H23N5O/c25-17-24(11-1-2-12-24)19-5-7-20(8-6-19)29-23(30)21-4-3-13-27-22(21)28-16-18-9-14-26-15-10-18/h3-10,13-15H,1-2,11-12,16H2,(H,27,28)(H,29,30)
comment: Rivoceranib (a.k.a. apatinib) is an orally bioavailable, small-molecule multitargeted tyrosine kinase inhibitor, with substantial inhibitory action against vascular endothelial growth factor receptor-2, but it also inhibits c-Kit and c-SRC tyrosine kinases <Reference id=25192/>. The drug is administered as the mesylate salt (PubChem CID 45139106). Its principal clinical effect is as an angiogenesis inhibitor.
iupac name: N-[4-(1-cyanocyclopentyl)phenyl]-2-(pyridin-4-ylmethylamino)pyridine-3-carboxamide
xref: CHEMBL3186534
synonym: YN968D1
synonym: apatinib (in China)
approved: t
ligand name: rivoceranib
type: SyntheticOrganicLigand

BMS-599626
in ch i key: LUJZZYWHBDHDQX-QFIPXVFZSA-N
in ch i: InChI=1S/C27H27FN8O3/c1-17-23(34-27(37)39-15-22-14-38-8-7-29-22)13-36-25(17)26(30-16-32-36)33-21-5-6-24-19(10-21)11-31-35(24)12-18-3-2-4-20(28)9-18/h2-6,9-11,13,16,22,29H,7-8,12,14-15H2,1H3,(H,34,37)(H,30,32,33)/t22-/m0/s1
comment: BMS-599626 is an orally bioavailable inhibitor of the HER1, HER2 and HER4 tyrosine kinases. Note that some biocativity data may be assiociated with the hydrochloride salt AC-480 (PubChem CID 46930994). This compound is being investigated as an antineoplastic agent <Reference id=25189/><Reference id=25188/>.<
iupac name: [(3S)-morpholin-3-yl]methyl N-[4-[[1-[(3-fluorophenyl)methyl]indazol-5-yl]amino]-5-methylpyrrolo[2,1-f][1,2,4]triazin-6-yl]carbamate
xref: CHEMBL1645462
synonym: AC1480 (free base)
synonym: AC480
synonym: BMS599626
synonym: BMS 599626
approved: f
ligand name: BMS-599626
type: SyntheticOrganicLigand

falnidamol
in ch i key: FTFRZXFNZVCRSK-UHFFFAOYSA-N
in ch i: InChI=1S/C18H19ClFN7/c1-27-6-4-11(5-7-27)25-18-21-9-15-16(26-18)17(23-10-22-15)24-12-2-3-14(20)13(19)8-12/h2-3,8-11H,4-7H2,1H3,(H,21,25,26)(H,22,23,24)
comment: Falnidamol is a selective and reversible inhibitor of EGFR and HER2.
iupac name: N-(3-chloro-4-fluorophenyl)-N'-(1-methylpiperidin-4-yl)pyrimido[4,5-e]pyrimidine-4,6-diamine
xref: CHEMBL258940
synonym: BIBX 1382
synonym: BIBX1382
synonym: BIBX-1382
approved: f
ligand name: falnidamol
type: SyntheticOrganicLigand

varlitinib
in ch i key: UWXSAYUXVSFDBQ-CYBMUJFWSA-N
comment: Varlitinib selectively and reversibly binds to both EGFR and HER2 and prevents their phosphorylation and activation, and is being investigated for the treatment of some types of cancer. Some bioactivity data may be linked to the tosylate salt (PubChem CID 56842258). This clinical candidate has completed Phase II clinical trials. Click here to view varlitinib trials registered with ClinicalTrials.gov.
iupac name: 4-N-[3-chloro-4-(1,3-thiazol-2-ylmethoxy)phenyl]-6-N-[(4R)-4-methyl-4,5-dihydro-1,3-oxazol-2-yl]quinazoline-4,6-diamine
xref: CHEMBL2103842
synonym: ARRY334543
synonym: ARRY-334543
approved: f
ligand name: varlitinib
type: SyntheticOrganicLigand

tiludronic acid
canonical SMILES: Clc1ccc(cc1)SC(P(=O)(O)O)P(=O)(O)O
isomeric SMILES: Clc1ccc(cc1)SC(P(=O)(O)O)P(=O)(O)O
in ch i key: DKJJVAGXPKPDRL-UHFFFAOYSA-N
in ch i: InChI=1S/C7H9ClO6P2S/c8-5-1-3-6(4-2-5)17-7(15(9,10)11)16(12,13)14/h1-4,7H,(H2,9,10,11)(H2,12,13,14)
comment: Tiludronic acid belongs to the same non-nitrogenous bisphosphonate drug family as <Ligand id=7184/> and clodronic acid (PubChem CID 25419). Marketed formulations contain tiludronate disodium (PubChem CID 60936).
iupac name: [(4-chlorophenyl)sulfanyl-phosphonomethyl]phosphonic acid
xref: CHEMBL1350
synonym: tiludronate
synonym: SR-41319
synonym: CIPsMBP
synonym: Skelid®
approved: t
ligand name: tiludronic acid
type: SyntheticOrganicLigand

AEE788
in ch i key: OONFNUWBHFSNBT-HXUWFJFHSA-N
in ch i: InChI=1S/C27H32N6/c1-3-32-13-15-33(16-14-32)18-21-9-11-23(12-10-21)25-17-24-26(28-19-29-27(24)31-25)30-20(2)22-7-5-4-6-8-22/h4-12,17,19-20H,3,13-16,18H2,1-2H3,(H2,28,29,30,31)/t20-/m1/s1
comment: AEE788 is a reversible inhibitor of EGFR, HER2 and VEGFR1-3 with antitumor and antiangiogenic activity <Reference id=25182/>. This compound has been evaluated in phase I clinical trial <Reference id=25183/> where inhibition of EGFR was reported.
iupac name: 6-[4-[(4-ethylpiperazin-1-yl)methyl]phenyl]-N-[(1R)-1-phenylethyl]-7H-pyrrolo[3,2-e]pyrimidin-4-amine
xref: CHEMBL587723
synonym: NVP-AEE788
synonym: AEE 788
approved: f
ligand name: AEE788
type: SyntheticOrganicLigand

PKI166
in ch i key: XRYJULCDUUATMC-CYBMUJFWSA-N
in ch i: InChI=1S/C20H18N4O/c1-13(14-5-3-2-4-6-14)23-19-17-11-18(24-20(17)22-12-21-19)15-7-9-16(25)10-8-15/h2-13,25H,1H3,(H2,21,22,23,24)/t13-/m1/s1
comment: PKI166 is an experimental, reversible inhibitor of epidermal growth factor receptor tyrosine kinase <Reference id=15289/>. This is compound 46 in <Reference id=25181/>. Development of this compound as a clinical candidate has been terminated.
iupac name: 4-[4-[[(1R)-1-phenylethyl]amino]-7H-pyrrolo[4,5-e]pyrimidin-6-yl]phenol
xref: CHEMBL1963502
synonym: NVP-PKI166
synonym: PKI-166
approved: f
ligand name: PKI166
type: SyntheticOrganicLigand

icotinib
in ch i key: QQLKULDARVNMAL-UHFFFAOYSA-N
in ch i: InChI=1S/C22H21N3O4/c1-2-16-4-3-5-17(12-16)25-22-18-13-20-21(14-19(18)23-15-24-22)29-11-9-27-7-6-26-8-10-28-20/h1,3-5,12-15H,6-11H2,(H,23,24,25)
comment: Icotinib is a selective, orally available epidermal growth factor receptor tyrosine kinase inhibitor <Reference id=25178/><Reference id=25179/><Reference id=25180/>. Icotinib is a 'pseudo' INN, that takes the form of an INN, but has not been submitted to the World Health Organisation for ratification.
iupac name: N-(3-ethynylphenyl)-7H,8H,10H,11H,13H,14H-1,4,7,10-tetraoxacyclododeca[2,3-g]quinazolin-4-amine
xref: CHEMBL2087361
synonym: BPI-2009H
synonym: Conmana®
approved: t
ligand name: icotinib
type: SyntheticOrganicLigand

simotinib
in ch i key: OXWUWXCJDBRCCG-UHFFFAOYSA-N
comment: Simotinib is an oral, epidermal growth factor receptor tyrosine kinase inhibitor <Reference id=25177/>. It was developed by Jiangsu Simcere Pharmaceutical Research Company in Nanjing, China. See also patent WO2010021918A1. Simotinib treatment is associated with serious adverse effects on gastrointestinal physiology <Reference id=33729/>.
iupac name: N-(3-chloro-4-fluorophenyl)-6-[2-(5,8-dioxa-10-azadispiro[2.0.4^{4}.3^{3}]undecan-10-yl)ethoxy]-7-methoxyquinazolin-4-amine
synonym: AL 6802
synonym: AL-6802
synonym: AL6802
synonym: SIM 6802
synonym: SIM6802
approved: t
ligand name: simotinib
type: SyntheticOrganicLigand

laquinimod
in ch i key: GKWPCEFFIHSJOE-UHFFFAOYSA-N
in ch i: InChI=1S/C19H17ClN2O3/c1-3-22(12-8-5-4-6-9-12)19(25)16-17(23)15-13(20)10-7-11-14(15)21(2)18(16)24/h4-11,23H,3H2,1-2H3
comment: Laquinimod is an experimental immunomodulator being investigated as an oral treatment for multiple sclerosis (MS) <Reference id=25171/><Reference id=25172/><Reference id=25173/><Reference id=25174/>.
iupac name: 5-chloro-N-ethyl-4-hydroxy-1-methyl-2-oxo-N-phenyl-1,2-dihydroquinoline-3-carboxamide
xref: CHEMBL66092
synonym: TV-5600
synonym: ABR-215062
approved: f
ligand name: laquinimod
type: SyntheticOrganicLigand

fanapanel
in ch i key: WZMQMKNCWDCCMT-UHFFFAOYSA-N
iupac name: [7-morpholin-4-yl-2,3-dioxo-6-(trifluoromethyl)-4H-quinoxalin-1-yl]methylphosphonic acid
xref: CHEMBL19892
synonym: ZK 200775
synonym: ZK-200775
synonym: ZK200775
approved: f
ligand name: fanapanel
type: SyntheticOrganicLigand

Duo3
canonical SMILES: Clc1cccc(c1CON=Cc1cc[n+](cc1)CCC[n+]1ccc(cc1)C=NOCc1c(Cl)cccc1Cl)Cl
isomeric SMILES: Clc1cccc(c1CO/N=C/c1cc[n+](cc1)CCC[n+]1ccc(cc1)/C=N/OCc1c(Cl)cccc1Cl)Cl
in ch i key: RAHLDBGBLYIYDN-WKCPDWHCSA-N
xref: CHEMBL32985
synonym: DUO3
approved: f
ligand name: Duo3
type: SyntheticOrganicLigand

cirazoline
canonical SMILES: C1CN=C(N1)COc1ccccc1C1CC1
isomeric SMILES: C1CN=C(N1)COc1ccccc1C1CC1
in ch i key: YAORIDZYZDUZCM-UHFFFAOYSA-N
in ch i: InChI=1S/C13H16N2O/c1-2-4-12(11(3-1)10-5-6-10)16-9-13-14-7-8-15-13/h1-4,10H,5-9H2,(H,14,15)
iupac name: 2-[(2-cyclopropylphenoxy)methyl]-4,5-dihydro-1H-imidazole
xref: CHEMBL13852
approved: f
ligand name: cirazoline
type: SyntheticOrganicLigand

C7/3-phth
in ch i key: OSALRKZRWVYPFR-UHFFFAOYSA-N
in ch i: InChI=1S/C33H46N4O4/c1-36(2,24-14-20-34-30(38)26-16-8-9-17-27(26)31(34)39)22-12-6-5-7-13-23-37(3,4)25-15-21-35-32(40)28-18-10-11-19-29(28)33(35)41/h8-11,16-19H,5-7,12-15,20-25H2,1-4H3/q+2
iupac name: 3-(1,3-dioxoisoindol-2-yl)propyl-[7-[3-(1,3-dioxoisoindol-2-yl)propyl-dimethylazaniumyl]heptyl]-dimethylazanium
xref: CHEMBL28407
synonym: heptane-1,7-bis(dimethyl-3'-phthalimidopropylammonium)
approved: f
ligand name: C7/3-phth
type: SyntheticOrganicLigand

VU0010010
in ch i key: IKKFWVKRPITRNW-UHFFFAOYSA-N
in ch i: InChI=1S/C17H18ClN3OS/c1-9-7-10(2)21-17-13(9)14(19)15(23-17)16(22)20-8-11-3-5-12(18)6-4-11/h3-7,14-15H,8,19H2,1-2H3,(H,20,22)
iupac name: 3-amino-N-[(4-chlorophenyl)methyl]-4,6-dimethyl-2H,3H-thieno[2,3-b]pyridine-2-carboxamide
xref: CHEMBL1212994
synonym: VU10010
synonym: compound 14 [PMID: 19201489]
approved: f
ligand name: VU0010010
type: SyntheticOrganicLigand

VU0119498
canonical SMILES: Brc1ccc(cc1)CN1c2ccccc2C(=O)C1=O
isomeric SMILES: Brc1ccc(cc1)CN1c2ccccc2C(=O)C1=O
in ch i key: DELLOEULSHGYCG-UHFFFAOYSA-N
in ch i: InChI=1S/C15H10BrNO2/c16-11-7-5-10(6-8-11)9-17-13-4-2-1-3-12(13)14(18)15(17)19/h1-8H,9H2
iupac name: 1-[(4-bromophenyl)methyl]indole-2,3-dione
xref: CHEMBL523685
synonym: VU 0119498
synonym: VU-0119498
synonym: STK215777
approved: f
ligand name: VU0119498
type: SyntheticOrganicLigand

ML375
in ch i key: GXBAKXRLQAPKEE-QHCPKHFHSA-N
iupac name: (9bS)-9b-(4-chlorophenyl)-1-(3,4-difluorobenzoyl)-2,3-dihydroimidazo[2,1-a]isoindol-5-one
xref: CHEMBL3105228
synonym: VU0483253-3
approved: f
ligand name: ML375
type: SyntheticOrganicLigand

testosterone decanoate
in ch i key: LBERVHLCXUMDOT-MPZZESAYSA-N
in ch i: InChI=1S/C29H46O3/c1-4-5-6-7-8-9-10-11-27(31)32-26-15-14-24-23-13-12-21-20-22(30)16-18-28(21,2)25(23)17-19-29(24,26)3/h20,23-26H,4-19H2,1-3H3/t23-,24-,25-,26-,28-,29-/m0/s1
comment: Testosterone decanoate is a synthetic <Ligand id=2858/> drug with improved bioavailability and metabolic half life compared to the endogenous hormone.
iupac name: [(8R,9S,10R,13S,14S,17S)-10,13-dimethyl-3-oxo-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl] decanoate
xref: CHEMBL1473654
approved: t
ligand name: testosterone decanoate
type: SyntheticOrganicLigand

testosterone isocaproate
in ch i key: PPYHLSBUTAPNGT-BKWLFHPQSA-N
in ch i: InChI=1S/C25H38O3/c1-16(2)5-10-23(27)28-22-9-8-20-19-7-6-17-15-18(26)11-13-24(17,3)21(19)12-14-25(20,22)4/h15-16,19-22H,5-14H2,1-4H3/t19-,20-,21-,22-,24-,25-/m0/s1
comment: Testosterone isocaproate is a <Ligand id=2858/> ester with improved bioavailability and metabolic half life compared to the endogenous hormone.
iupac name: [(8R,9S,10R,13S,14S,17S)-10,13-dimethyl-3-oxo-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl] 4-methylpentanoate
xref: CHEMBL3189011
synonym: testosterone 4-methylvalerate
approved: t
ligand name: testosterone isocaproate
type: SyntheticOrganicLigand

testosterone phenylpropionate
in ch i key: HHSXYDOROIURIP-FEZCWRLCSA-N
in ch i: InChI=1S/C28H36O3/c1-27-16-14-21(29)18-20(27)9-10-22-23-11-12-25(28(23,2)17-15-24(22)27)31-26(30)13-8-19-6-4-3-5-7-19/h3-7,18,22-25H,8-17H2,1-2H3/t22-,23-,24-,25-,27-,28-/m0/s1
comment: Testosterone phenylpropionate is a <Ligand id=2858/> ester with improved bioavailability and metabolic half life compared to the endogenous hormone.
iupac name: [(8R,9S,10R,13S,14S,17S)-10,13-dimethyl-3-oxo-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl] 3-phenylpropanoate
xref: CHEMBL2356993
synonym: testosterone 17-phenylpropionate
synonym: testosterone hydrocinnamate
approved: t
ligand name: testosterone phenylpropionate
type: SyntheticOrganicLigand

cobimetinib
in ch i key: BSMCAPRUBJMWDF-KRWDZBQOSA-N
comment: Cobimetinib is an allosteric inhibitor of MEK serine/threonine protein kinases, with selectivity for MEK1 and MEK2 <Reference id=30152/>. Note that cobimetinib has been erroneously referred to as cometinib and this has propagated in online resources- cometinib is not an official synonym.
iupac name: [3,4-difluoro-2-[(2-fluoro-4-iodophenyl)amino]phenyl]-[3-hydroxy-3-[(2S)-piperidin-2-yl]azetidin-1-yl]methanone
xref: CHEMBL2146883
synonym: cometinib
synonym: Cotellic®
synonym: XL518
synonym: GDC-0973
synonym: XL-518
synonym: cobimetinib butyrate
synonym: cobimetinib fumarate
approved: t
ligand name: cobimetinib
type: SyntheticOrganicLigand

BP 897
in ch i key: MNHDKMDLOJSCGN-UHFFFAOYSA-N
in ch i: InChI=1S/C26H31N3O2/c1-31-25-11-5-4-10-24(25)29-18-16-28(17-19-29)15-7-6-14-27-26(30)23-13-12-21-8-2-3-9-22(21)20-23/h2-5,8-13,20H,6-7,14-19H2,1H3,(H,27,30)
comment: BP 897 is a partial agonist of the dopamine D3 receptor <Reference id=2925/>.
iupac name: N-[4-[4-(2-methoxyphenyl)piperazin-1-yl]butyl]naphthalene-2-carboxamide
xref: CHEMBL25236
synonym: BP-897
synonym: BP897
approved: f
ligand name: BP 897
type: SyntheticOrganicLigand

fosaprepitant
in ch i key: BARDROPHSZEBKC-OITMNORJSA-N
comment: Marketed formulations contain fosaprepitant dimeglumine.
iupac name: [3-[[(2R,3S)-2-[(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethoxy]-3-(4-fluorophenyl)morpholin-4-yl]methyl]-5-oxo-2H-1,2,4-triazol-1-yl]phosphonic acid
xref: CHEMBL1199324
synonym: Ivemend®
synonym: Emend for Injection®
synonym: MK-0517
approved: t
ligand name: fosaprepitant
type: SyntheticOrganicLigand

thiotepa
canonical SMILES: S=P(N1CC1)(N1CC1)N1CC1
isomeric SMILES: S=P(N1CC1)(N1CC1)N1CC1
in ch i key: FOCVUCIESVLUNU-UHFFFAOYSA-N
in ch i: InChI=1S/C6H12N3PS/c11-10(7-1-2-7,8-3-4-8)9-5-6-9/h1-6H2
comment: Thiotepa is an organophosphorus DNA alkylating anti-cancer chemotherapeutic <Reference id=31262/>.
iupac name: tris(aziridin-1-yl)-sulfanylidenephosphorane
xref: CHEMBL671
synonym: Tiofosfamid
synonym: Tiofosyl
synonym: Girostan
synonym: Tepadina®
synonym: Thioplex®
approved: t
ligand name: thiotepa
type: SyntheticOrganicLigand

uramustine
canonical SMILES: ClCCN(c1c[nH]c(=O)[nH]c1=O)CCCl
isomeric SMILES: ClCCN(c1c[nH]c(=O)[nH]c1=O)CCCl
in ch i key: IDPUKCWIGUEADI-UHFFFAOYSA-N
in ch i: InChI=1S/C8H11Cl2N3O2/c9-1-3-13(4-2-10)6-5-11-8(15)12-7(6)14/h5H,1-4H2,(H2,11,12,14,15)
comment: Chemically uramustine is a derivative of nitrogen mustard and uracil. It is used clinically as a DNA alkylating anti-cancer chemotherapeutic.
iupac name: 5-[bis(2-chloroethyl)amino]-1H-pyrimidine-2,4-dione
xref: CHEMBL1488
synonym: U-8344
synonym: Nordopan
synonym: Demethyldopan
synonym: Uracil Mustard®
approved: t
ligand name: uramustine
type: SyntheticOrganicLigand

melphalan
canonical SMILES: ClCCN(c1ccc(cc1)CC(C(=O)O)N)CCCl
isomeric SMILES: ClCCN(c1ccc(cc1)C[C@@H](C(=O)O)N)CCCl
in ch i key: SGDBTWWWUNNDEQ-LBPRGKRZSA-N
comment: Marketed formulations may contain melphalan hydrochloride.
iupac name: (2S)-2-amino-3-[4-[bis(2-chloroethyl)amino]phenyl]propanoic acid
xref: CHEMBL852
synonym: L-phenylalanine mustard (L-PAM)
synonym: L-sarcolysine
synonym: CB-3025
synonym: melfalan
synonym: Alkeran®
synonym: Sarcolysin®
synonym: Phelinun®
approved: t
ligand name: melphalan
type: SyntheticOrganicLigand

enclomiphene
isomeric SMILES: CCN(CCOc1ccc(cc1)/C(=C(/c1ccccc1)/Cl)/c1ccccc1)CC
in ch i key: GKIRPKYJQBWNGO-OCEACIFDSA-N
in ch i: InChI=1S/C26H28ClNO/c1-3-28(4-2)19-20-29-24-17-15-22(16-18-24)25(21-11-7-5-8-12-21)26(27)23-13-9-6-10-14-23/h5-18H,3-4,19-20H2,1-2H3/b26-25+
comment: Enclomiphene is the trans isomer component in the racemate drug <Ligand id=4159/> and has also been assigned an INN in its own right.
iupac name: 2-[4-[(E)-2-chloro-1,2-di(phenyl)ethenyl]phenoxy]-N,N-diethylethanamine
xref: CHEMBL954
synonym: Androxal®
synonym: enclomiphene citrate
approved: f
ligand name: enclomiphene
type: SyntheticOrganicLigand

betanidine
canonical SMILES: CNC(=NC)NCc1ccccc1
isomeric SMILES: CNC(=NC)NCc1ccccc1
in ch i key: NIVZHWNOUVJHKV-UHFFFAOYSA-N
in ch i: InChI=1S/C10H15N3/c1-11-10(12-2)13-8-9-6-4-3-5-7-9/h3-7H,8H2,1-2H3,(H2,11,12,13)
comment: Betanidine is a guanidinium-based sympatholytic antihypertensive drug.
iupac name: 2,3-dimethyl-1-(phenylmethyl)guanidine
xref: CHEMBL1201260
synonym: BW-467-C-60
synonym: bethanidine
synonym: Tenathan®
approved: t
ligand name: betanidine
type: SyntheticOrganicLigand

guaifenesin
canonical SMILES: OCC(COc1ccccc1OC)O
isomeric SMILES: OCC(COc1ccccc1OC)O
in ch i key: HSRJKNPTNIJEKV-UHFFFAOYSA-N
in ch i: InChI=1S/C10H14O4/c1-13-9-4-2-3-5-10(9)14-7-8(12)6-11/h2-5,8,11-12H,6-7H2,1H3
comment: The approved drug is a racemic mixture of enantiomers; R-guaifenesin and S-guaifenesin. We show the non-stereo structure to represent the mixture.
iupac name: 3-(2-methoxyphenoxy)propane-1,2-diol
xref: CHEMBL980
synonym: guaiphenesin
synonym: glyceryl guaiacolate
synonym: Guaiacol Glyceryl Ether
synonym: Methphenoxydiol
synonym: Humabid
synonym: Mucinex®
approved: t
ligand name: guaifenesin
type: SyntheticOrganicLigand

phenazopyridine
canonical SMILES: Nc1ccc(c(n1)N)N=Nc1ccccc1
isomeric SMILES: Nc1ccc(c(n1)N)N=Nc1ccccc1
in ch i key: QPFYXYFORQJZEC-UHFFFAOYSA-N
in ch i: InChI=1S/C11H11N5/c12-10-7-6-9(11(13)14-10)16-15-8-4-2-1-3-5-8/h1-7H,(H4,12,13,14)
comment: This ligand is also represented on ChEMBL by the entry with ID CHEMBL1242.
iupac name: 3-phenyldiazenylpyridine-2,6-diamine
xref: CHEMBL1625467
synonym: W-1655
synonym: NC-150
synonym: Pyridiate
synonym: Baridium
synonym: Urogesic
synonym: Sedural
synonym: Viridium
synonym: Urodine
synonym: Pyridium®
approved: t
ligand name: phenazopyridine
type: SyntheticOrganicLigand

secobarbital
canonical SMILES: CCCC(C1(CC=C)C(=O)NC(=O)NC1=O)C
isomeric SMILES: CCCC(C1(CC=C)C(=O)NC(=O)NC1=O)C
in ch i key: KQPKPCNLIDLUMF-UHFFFAOYSA-N
in ch i: InChI=1S/C12H18N2O3/c1-4-6-8(3)12(7-5-2)9(15)13-11(17)14-10(12)16/h5,8H,2,4,6-7H2,1,3H3,(H2,13,14,15,16,17)
comment: The approved drug is a racemic mixture of enantiomers; R-secobarbital and S-secobarbital. We show the non-stereo structure to represent the mixture.
iupac name: 5-pentan-2-yl-5-prop-2-enyl-1,3-diazinane-2,4,6-trione
xref: CHEMBL447
synonym: Meballymal
synonym: Quinalbarbitone
synonym: Seconal®
approved: t
ligand name: secobarbital
type: SyntheticOrganicLigand

trimethobenzamide
in ch i key: FEZBIKUBAYAZIU-UHFFFAOYSA-N
in ch i: InChI=1S/C21H28N2O5/c1-23(2)10-11-28-17-8-6-15(7-9-17)14-22-21(24)16-12-18(25-3)20(27-5)19(13-16)26-4/h6-9,12-13H,10-11,14H2,1-5H3,(H,22,24)
comment: Marketed formulations contain trimethobenzamide hydrochloride.
iupac name: N-[[4-(2-dimethylaminoethoxy)phenyl]methyl]-3,4,5-trimethoxybenzamide
xref: CHEMBL1201256
synonym: Tigan®
synonym: trimethobenzamide hydrochloride
synonym: Tribenzagan
synonym: Benzacot
synonym: Stemetic
synonym: Tebamide
approved: t
ligand name: trimethobenzamide
type: SyntheticOrganicLigand

trimetrexate
in ch i key: NOYPYLRCIDNJJB-UHFFFAOYSA-N
in ch i: InChI=1S/C19H23N5O3/c1-10-11(5-6-13-16(10)18(20)24-19(21)23-13)9-22-12-7-14(25-2)17(27-4)15(8-12)26-3/h5-8,22H,9H2,1-4H3,(H4,20,21,23,24)
comment: Trimetrexate is a quinazoline derivative dihydrofolate reductase inhibitor <Reference id=24971/>. Chemically it is a <Ligand id=4815/> (MTX) analogue.
xref: CHEMBL119
synonym: trimetrexate glucuronate
synonym: CI-898
synonym: Neutrexin®
approved: t
ligand name: trimetrexate
type: SyntheticOrganicLigand

phensuximide
canonical SMILES: CN1C(=O)CC(C1=O)c1ccccc1
isomeric SMILES: CN1C(=O)CC(C1=O)c1ccccc1
in ch i key: WLWFNJKHKGIJNW-UHFFFAOYSA-N
in ch i: InChI=1S/C11H11NO2/c1-12-10(13)7-9(11(12)14)8-5-3-2-4-6-8/h2-6,9H,7H2,1H3
comment: Phensuximide is a racemic mixture of enantiomers; R-phensuximide and S-phensuximide. We show the non-stereo molecule to represent the mixture. One tautomer is also recognised, with PubChem CID 53881854
iupac name: 1-methyl-3-phenylpyrrolidine-2,5-dione
xref: CHEMBL797
synonym: Succitimal
synonym: Milonton
synonym: Lifene®
synonym: Milontin®
approved: f
ligand name: phensuximide
type: SyntheticOrganicLigand

benzonatate
in ch i key: MAFMQEKGGFWBAB-UHFFFAOYSA-N
in ch i: InChI=1S/C30H53NO11/c1-3-4-9-31-29-7-5-28(6-8-29)30(32)42-27-26-41-25-24-40-23-22-39-21-20-38-19-18-37-17-16-36-15-14-35-13-12-34-11-10-33-2/h5-8,31H,3-4,9-27H2,1-2H3
comment: Benzonatate is a non-narcotic antitussive. It is classified as a butylamine compound, and has structural similatities to ester type local anesthetics (e.g. <Ligand id=4291/> and tetracaine). It has reduced abuse potential compared to opioid-like antitussives.
iupac name: 2-[2-[2-[2-[2-[2-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethyl 4-butylaminobenzoate
xref: CHEMBL1374379
synonym: Tessalin
synonym: Ventussin
synonym: Tessalon®
synonym: Zonatuss®
approved: t
ligand name: benzonatate
type: SyntheticOrganicLigand

carisoprodol
canonical SMILES: CCCC(COC(=O)N)(COC(=O)NC(C)C)C
isomeric SMILES: CCCC(COC(=O)N)(COC(=O)NC(C)C)C
in ch i key: OFZCIYFFPZCNJE-UHFFFAOYSA-N
in ch i: InChI=1S/C12H24N2O4/c1-5-6-12(4,7-17-10(13)15)8-18-11(16)14-9(2)3/h9H,5-8H2,1-4H3,(H2,13,15)(H,14,16)
comment: Carisoprodol is a racemic mixture of enantiomers; R-carisoprodol and S-carisoprodol. We show the non-stereo molecule to represent the mixture.
iupac name: [2-(carbamoyloxymethyl)-2-methylpentyl] N-propan-2-ylcarbamate
xref: CHEMBL1233
synonym: Rela
synonym: Sanoma
synonym: Carisoma
synonym: Soma®
approved: t
ligand name: carisoprodol
type: SyntheticOrganicLigand

metaxalone
canonical SMILES: O=C1NCC(O1)COc1cc(C)cc(c1)C
isomeric SMILES: O=C1NCC(O1)COc1cc(C)cc(c1)C
in ch i key: IMWZZHHPURKASS-UHFFFAOYSA-N
in ch i: InChI=1S/C12H15NO3/c1-8-3-9(2)5-10(4-8)15-7-11-6-13-12(14)16-11/h3-5,11H,6-7H2,1-2H3,(H,13,14)
comment: Metaxalone is a racemic mixture of two enantiomers; R-metaxalone and S-metaxalone. We show the non-stereo structure to represent the mixture.
iupac name: 5-[(3,5-dimethylphenoxy)methyl]-1,3-oxazolidin-2-one
xref: CHEMBL1079604
synonym: AHR-438
synonym: Skelaxin®
approved: t
ligand name: metaxalone
type: SyntheticOrganicLigand

cromoglicic acid
in ch i key: IMZMKUWMOSJXDT-UHFFFAOYSA-N
in ch i: InChI=1S/C23H16O11/c24-11(9-31-14-3-1-5-16-20(14)12(25)7-18(33-16)22(27)28)10-32-15-4-2-6-17-21(15)13(26)8-19(34-17)23(29)30/h1-8,11,24H,9-10H2,(H,27,28)(H,29,30)
comment: Cromoglicic acid (cromolyn) is regarded as a mast cell stabilising drug, although its exact mechanism of action appears to be much more complicated. Recent reports suggest that cromolyn inhibits glycogen synthase kinase 3β and may therefore have potential to treat diabetes and obesity <Reference id=24964/> and may prove effective in treating insulin-induced lipoatrophy <Reference id=24965/>. It also has reported potential anti-fibrotic action through agonism of GPR35 <Reference id=36209/><Reference id=36210/>.
iupac name: 5-[3-(2-carboxy-4-oxochromen-5-yl)oxy-2-hydroxypropoxy]-4-oxochromene-2-carboxylic acid
xref: CHEMBL428880
synonym: cromolyn
synonym: cromoglycate
synonym: sodium cromoglicate
synonym: cromolyn sodium
synonym: FPL-670
synonym: Gastrocrom
synonym: Crolom
synonym: Nasalcrom
synonym: Cromoptic
synonym: Intal®
synonym: Opticrom®
approved: t
ligand name: cromoglicic acid
type: SyntheticOrganicLigand

nedocromil
in ch i key: RQTOOFIXOKYGAN-UHFFFAOYSA-N
in ch i: InChI=1S/C19H17NO7/c1-3-5-9-16-10(13(21)7-12(18(23)24)20(16)4-2)6-11-14(22)8-15(19(25)26)27-17(9)11/h6-8H,3-5H2,1-2H3,(H,23,24)(H,25,26)
comment: Nedocromil is considered to be a mast cell stabilising drug. Chemically it belongs to the benzopyrone family of compounds. In the US, production of inhaled nedocromil was terminated in 2008.
iupac name: 9-ethyl-4,6-dioxo-10-propylpyrano[5,6-g]quinoline-2,8-dicarboxylic acid
xref: CHEMBL746
synonym: FPL-59002
synonym: nedocromil sodium
synonym: Rapitil®
synonym: Tilade®
approved: t
ligand name: nedocromil
type: SyntheticOrganicLigand

fludroxycortide
in ch i key: POPFMWWJOGLOIF-XWCQMRHXSA-N
in ch i: InChI=1S/C24H33FO6/c1-21(2)30-19-9-14-13-8-16(25)15-7-12(27)5-6-22(15,3)20(13)17(28)10-23(14,4)24(19,31-21)18(29)11-26/h7,13-14,16-17,19-20,26,28H,5-6,8-11H2,1-4H3/t13-,14-,16-,17-,19+,20+,22-,23-,24+/m0/s1
comment: Fludroxycortide is a synthetic topical glucocorticoid, used clinically for its antiinflammatory action <Reference id=31261/>.
xref: CHEMBL1201012
synonym: flurandrenolone
synonym: flurandrenolide
synonym: Cordran®
synonym: Haelan®
approved: t
ligand name: fludroxycortide
type: SyntheticOrganicLigand

prednicarbate
in ch i key: FNPXMHRZILFCKX-KAJVQRHHSA-N
in ch i: InChI=1S/C27H36O8/c1-5-22(31)34-15-21(30)27(35-24(32)33-6-2)12-10-19-18-8-7-16-13-17(28)9-11-25(16,3)23(18)20(29)14-26(19,27)4/h9,11,13,18-20,23,29H,5-8,10,12,14-15H2,1-4H3/t18-,19-,20-,23+,25-,26-,27-/m0/s1
comment: Prednicarbate is a nonhalogenated derivative of <Ligand id=2866/>.
iupac name: [2-[(8S,9S,10R,11S,13S,14S,17R)-17-ethoxycarbonyloxy-11-hydroxy-10,13-dimethyl-3-oxo-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-yl]-2-oxoethyl] propanoate
xref: CHEMBL1200386
synonym: Hoe 777
synonym: Hoe-777
synonym: Peitel
synonym: S-770777
synonym: Dermatop®
approved: t
ligand name: prednicarbate
type: SyntheticOrganicLigand

levomepromazine
canonical SMILES: COc1ccc2c(c1)N(CC(CN(C)C)C)c1c(S2)cccc1
in ch i key: VRQVVMDWGGWHTJ-CQSZACIVSA-N
in ch i: InChI=1S/C19H24N2OS/c1-14(12-20(2)3)13-21-16-7-5-6-8-18(16)23-19-10-9-15(22-4)11-17(19)21/h5-11,14H,12-13H2,1-4H3/t14-/m1/s1
comment: Marketed formulations contain either levomepromazine hydrochloride or levomepromazine maleate.
iupac name: (2R)-3-(2-methoxyphenothiazin-10-yl)-N,N,2-trimethylpropan-1-amine
xref: CHEMBL1764
synonym: methotrimeprazine
synonym: SK&F-5116
synonym: RP-7044
synonym: Tisercin
synonym: CL-36467
synonym: CL-39743
synonym: Nirvan
synonym: Nosinan®
synonym: Levoprome®
synonym: Nozinan®
approved: t
ligand name: levomepromazine
type: SyntheticOrganicLigand

ropivacaine
canonical SMILES: CCCN1CCCCC1C(=O)Nc1c(C)cccc1C
isomeric SMILES: CCCN1CCCC[C@H]1C(=O)Nc1c(C)cccc1C
in ch i key: ZKMNUMMKYBVTFN-HNNXBMFYSA-N
in ch i: InChI=1S/C17H26N2O/c1-4-11-19-12-6-5-10-15(19)17(20)18-16-13(2)8-7-9-14(16)3/h7-9,15H,4-6,10-12H2,1-3H3,(H,18,20)/t15-/m0/s1
comment: Ropivacaine is an amino amide local anaesthetic. We show the (S) enantiomer here, but the name can also be used to refer to the racemic mixture of optical isomers.
iupac name: (2S)-N-(2,6-dimethylphenyl)-1-propylpiperidine-2-carboxamide
xref: CHEMBL1077896
synonym: 1-propyl-2',6'-pipecoloxylidide
synonym: LEA-103
synonym: AL-381
synonym: Naropin®
synonym: Narapin
synonym: ropivacaine hydrochloride
approved: t
ligand name: ropivacaine
type: SyntheticOrganicLigand

benzatropine
canonical SMILES: CN1C2CCC1CC(C2)OC(c1ccccc1)c1ccccc1
in ch i key: GIJXKZJWITVLHI-PMOLBWCYSA-N
in ch i: InChI=1S/C21H25NO/c1-22-18-12-13-19(22)15-20(14-18)23-21(16-8-4-2-5-9-16)17-10-6-3-7-11-17/h2-11,18-21H,12-15H2,1H3/t18-,19+,20+
comment: Benzatropine (benztropine) is an anticholinergic drug. PubChem CID 1201549 represents an alternative isomer of this compound. Benzatropine is reported as an inhibitor of the neutral amino acid transporter B0AT1 (SLC6A19) <Reference id=32123/>, a recently identified molecular target for treatment of type 2 diabetes and related disorders <Reference id=32124/>. Note that the mesylate salt was used in the experiments reported in <Reference id=32123/>.
iupac name: (1R,5S)-3-[di(phenyl)methoxy]-8-methyl-8-azabicyclo[3.2.1]octane
xref: CHEMBL1201203
synonym: benztropine
synonym: benztropine mesylate
synonym: Cogentin®
approved: t
ligand name: benzatropine
type: SyntheticOrganicLigand

isotretinoin
isomeric SMILES: C/C(=C/C=C/C(=C/C(=O)O)/C)/C=C/C1=C(C)CCCC1(C)C
in ch i key: SHGAZHPCJJPHSC-XFYACQKRSA-N
in ch i: InChI=1S/C20H28O2/c1-15(8-6-9-16(2)14-19(21)22)11-12-18-17(3)10-7-13-20(18,4)5/h6,8-9,11-12,14H,7,10,13H2,1-5H3,(H,21,22)/b9-6+,12-11+,15-8+,16-14-
comment: Isotretinoin is a retinoid type drug ie it is a vitamin A-like molecule. It is the endogenous agonist for retinoic acid receptors (RARs).
iupac name: (2Z,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)nona-2,4,6,8-tetraenoic acid
xref: CHEMBL547
synonym: 13-cis retinoic acid
synonym: Sotret
synonym: Amnesteem
synonym: Claravis
synonym: Clarus
synonym: Roaccutane
synonym: Accutane®
approved: t
ligand name: isotretinoin
type: SyntheticOrganicLigand

etretinate
isomeric SMILES: CCOC(=O)/C=C(/C=C/C=C(/C=C/c1c(C)cc(c(c1C)C)OC)/C)/C
in ch i key: HQMNCQVAMBCHCO-DJRRULDNSA-N
in ch i: InChI=1S/C23H30O3/c1-8-26-23(24)14-17(3)11-9-10-16(2)12-13-21-18(4)15-22(25-7)20(6)19(21)5/h9-15H,8H2,1-7H3/b11-9+,13-12+,16-10+,17-14+
comment: Etretinate is a highly lipophilic second-generation retinoid. Its use has largely been discontinued as it was discovered to be a long-acting teratogen, with detectable levels in plasma up to three years post-therapy.
iupac name: ethyl 9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethylnona-2,4,6,8-tetraenoate
xref: CHEMBL464
synonym: Ro-109359
synonym: Tegison®
approved: t
ligand name: etretinate
type: SyntheticOrganicLigand

acitretin
isomeric SMILES: COc1cc(C)c(c(c1C)C)/C=C/C(=C/C=C/C(=C/C(=O)O)/C)/C
in ch i key: IHUNBGSDBOWDMA-AQFIFDHZSA-N
in ch i: InChI=1S/C21H26O3/c1-14(8-7-9-15(2)12-21(22)23)10-11-19-16(3)13-20(24-6)18(5)17(19)4/h7-13H,1-6H3,(H,22,23)/b9-7+,11-10+,14-8+,15-12+
comment: Acitretin is a second generation retinoid drug. Acitretin is an active metabolite of <Ligand id=7599/>, but may also be reverse metabolised back to etretinate.
iupac name: (2E,4E,6E,8E)-9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethylnona-2,4,6,8-tetraenoic acid
xref: CHEMBL1131
synonym: Ro-101670000
synonym: Neotigason
synonym: Soriatane®
approved: t
ligand name: acitretin
type: SyntheticOrganicLigand

pralidoxime
canonical SMILES: ON=Cc1cccc[n+]1C
isomeric SMILES: O/N=C/c1cccc[n+]1C
in ch i key: JBKPUQTUERUYQE-UHFFFAOYSA-O
in ch i: InChI=1S/C7H8N2O/c1-9-5-3-2-4-7(9)6-8-10/h2-6H,1H3/p+1
comment: Usually available as the chloride or methiodide salts.
iupac name: (1-methylpyridin-2-ylidene)methyl-oxoazanium
xref: CHEMBL1420
synonym: 2-PAM
synonym: Protopam
synonym: Protopam Chloride
synonym: Duodote
synonym: Contrathion®
synonym: pralidoxime chloride
approved: t
ligand name: pralidoxime
type: SyntheticOrganicLigand

(+)-propranolol
canonical SMILES: OC(COc1cccc2c1cccc2)CNC(C)C
isomeric SMILES: O[C@@H](COc1cccc2c1cccc2)CNC(C)C
in ch i key: AQHHHDLHHXJYJD-CQSZACIVSA-N
in ch i: InChI=1S/C16H21NO2/c1-12(2)17-10-14(18)11-19-16-9-5-7-13-6-3-4-8-15(13)16/h3-9,12,14,17-18H,10-11H2,1-2H3/t14-/m1/s1
comment: A component of the approved drug propranolol. Propranolol is a racemic mixture of two enantiomers (+)-propranolol, and (-)-propranolol.
iupac name: (2R)-1-naphthalen-1-yloxy-3-(propan-2-ylamino)propan-2-ol
xref: CHEMBL275742
synonym: R(+)-propranolol
synonym: dextropropranolol
approved: f
ligand name: (+)-propranolol
type: SyntheticOrganicLigand

levorphanol
canonical SMILES: Oc1ccc2c(c1)C13CCCCC3C(C2)N(CC1)C
in ch i key: JAQUASYNZVUNQP-USXIJHARSA-N
in ch i: InChI=1S/C17H23NO/c1-18-9-8-17-7-3-2-4-14(17)16(18)10-12-5-6-13(19)11-15(12)17/h5-6,11,14,16,19H,2-4,7-10H2,1H3/t14-,16+,17+/m0/s1
comment: Levorphanol is an opioid analgesic. Chemically it is the levorotatory optical isomer of racemorphan (PubChem CID 3918).
xref: CHEMBL592
synonym: (-) 3-hydroxy-N-methylmorphinan
synonym: levorphanol tartrate
synonym: levorphanol hydrochloride
synonym: Levo-Dromoran®
approved: t
ligand name: levorphanol
type: SyntheticOrganicLigand

dihydrocodeine
canonical SMILES: COc1ccc2c3c1OC1C43CCN(C(C2)C4CCC1O)C
in ch i key: RBOXVHNMENFORY-DNJOTXNNSA-N
in ch i: InChI=1S/C18H23NO3/c1-19-8-7-18-11-4-5-13(20)17(18)22-16-14(21-2)6-3-10(15(16)18)9-12(11)19/h3,6,11-13,17,20H,4-5,7-9H2,1-2H3/t11-,12+,13-,17-,18-/m0/s1
comment: Dihydrocodeine is a semi-synthetic opioid analgesic.
iupac name: (4R,4aR,7S,7aR,12bS)-9-methoxy-3-methyl-2,4,4a,5,6,7,7a,13-octahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinoline-7-ol
xref: CHEMBL1595
synonym: dihydrocodeine bitartrate
synonym: DF-118
synonym: Drocode
synonym: Parzone
synonym: Paracodin
synonym: Fortuss
synonym: Dicogesic®
synonym: Paracodeine®
approved: t
ligand name: dihydrocodeine
type: NaturalProductLigand

dextropropoxyphene
in ch i key: XLMALTXPSGQGBX-GCJKJVERSA-N
in ch i: InChI=1S/C22H29NO2/c1-5-21(24)25-22(18(2)17-23(3)4,20-14-10-7-11-15-20)16-19-12-8-6-9-13-19/h6-15,18H,5,16-17H2,1-4H3/t18-,22+/m1/s1
comment: Dextropropoxyphene is principally an opioid analgesic. Chemically it is an optical isomer of levopropoxyphene (the (2R,3S) optical isomer with PubChem CID 200742); dextropropoxyphene being the (2S,3R) enantiomer. Marketing in Europe and the US has been discontinued due to concerns of fatal overdoses and heart arrhythmias.
iupac name: [(2S,3R)-4-dimethylamino-3-methyl-1,2-di(phenyl)butan-2-yl] propanoate
xref: CHEMBL1213351
synonym: (+)-alpha-propoxyphene
synonym: propoxyphene
synonym: Dolene
synonym: Kesso-Gesic
synonym: Propoxyphene HCl
synonym: Darvon®
approved: t
ligand name: dextropropoxyphene
type: SyntheticOrganicLigand

difenoxin
in ch i key: UFIVBRCCIRTJTN-UHFFFAOYSA-N
in ch i: InChI=1S/C28H28N2O2/c29-22-28(24-12-6-2-7-13-24,25-14-8-3-9-15-25)18-21-30-19-16-27(17-20-30,26(31)32)23-10-4-1-5-11-23/h1-15H,16-21H2,(H,31,32)
comment: Difenoxin is an active metabolite of <Ligand id=7164/>.
iupac name: 1-[3-cyano-3,3-di(phenyl)propyl]-4-phenylpiperidine-4-carboxylic acid
xref: CHEMBL1201321
synonym: R-15403
synonym: MCN-JR-15,403-11
synonym: difenoxin hydrochloride
synonym: Motofen®
approved: t
ligand name: difenoxin
type: SyntheticOrganicLigand

butorphanol
in ch i key: IFKLAQQSCNILHL-QHAWAJNXSA-N
in ch i: InChI=1S/C21H29NO2/c23-17-7-6-16-12-19-21(24)9-2-1-8-20(21,18(16)13-17)10-11-22(19)14-15-4-3-5-15/h6-7,13,15,19,23-24H,1-5,8-12,14H2/t19-,20+,21-/m1/s1
comment: Our representation of this drug and that contained in the ChEMBL and PubChem links exactly matches the structure in the INN record for butorphanol. PubChem CID 6916249 shows a different stereoisomer.
xref: CHEMBL33986
synonym: LEVO-BC-2627
synonym: Torbutrol
synonym: Torbugesic
synonym: Stadol
synonym: butorphanol tartrate
approved: t
ligand name: butorphanol
type: SyntheticOrganicLigand

etonogestrel
in ch i key: GCKFUYQCUCGESZ-BPIQYHPVSA-N
in ch i: InChI=1S/C22H28O2/c1-4-21-13-14(3)20-17-9-7-16(23)12-15(17)6-8-18(20)19(21)10-11-22(21,24)5-2/h2,12,17-20,24H,3-4,6-11,13H2,1H3/t17-,18-,19-,20+,21-,22-/m0/s1
comment: Etonogestrel is the active metabolite of the inactive prodrug desogestrel.
iupac name: (8S,9S,10R,13S,14S,17R)-13-ethyl-17-ethynyl-17-hydroxy-11-methylidene-2,6,7,8,9,10,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-3-one
xref: CHEMBL1531
synonym: ORG-3236
synonym: NuvaRing
synonym: 3-keto-desogestrel
synonym: Nexplanon®
synonym: Implanon®
approved: t
ligand name: etonogestrel
type: SyntheticOrganicLigand

ceruletide
in ch i key: YRALAIOMGQZKOW-HYAOXDFASA-N
comment: Ceruletide is a decapeptide derivative of cholecystokinin with the amino acid sequence is Pglu-Gln-Asp-Tyr[SO3H]-Thr-Gly-Trp-Met-Asp-Phe-NH2 and originally isolated from the skin of the Australian green tree frog, Litoria caerulea. In the research setting ceruletide can be used to induce pancreatitis in experimental animal models.
iupac name: (3S)-3-[[(2S)-5-amino-5-oxo-2-[[(2S)-5-oxopyrrolidine-2-carbonyl]amino]pentanoyl]amino]-4-[[(2S)-1-[[(2S,3R)-1-[[2-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-amino-1-oxo-3-phenylpropan-2-yl]amino]-3-carboxy-1-oxopropan-2-yl]amino]-4-methylsulfanyl-1-oxobutan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-hydroxy-1-oxobutan-2-yl]amino]-1-oxo-3-(4-sulfooxyphenyl)propan-2-yl]amino]-4-oxobutanoic acid
xref: CHEMBL1201355
synonym: ceruletide diethylamine
synonym: cerulein
synonym: caerulein
synonym: Tymtran®
approved: t
ligand name: ceruletide
type: SyntheticOrganicLigand

dexbrompheniramine
canonical SMILES: CN(CCC(c1ccccn1)c1ccc(cc1)Br)C
isomeric SMILES: CN(CC[C@H](c1ccccn1)c1ccc(cc1)Br)C
in ch i key: ZDIGNSYAACHWNL-HNNXBMFYSA-N
in ch i: InChI=1S/C16H19BrN2/c1-19(2)12-10-15(16-5-3-4-11-18-16)13-6-8-14(17)9-7-13/h3-9,11,15H,10,12H2,1-2H3/t15-/m0/s1
comment: Chemically, dexbrompheniramine is the pharmacologically active dextrorotatory isomer of <Ligand id=7133/>.
iupac name: (3S)-3-(4-bromophenyl)-N,N-dimethyl-3-pyridin-2-ylpropan-1-amine
xref: CHEMBL1201287
synonym: D-brompheniramine
synonym: Disomer®
approved: t
ligand name: dexbrompheniramine
type: SyntheticOrganicLigand

alcaftadine
canonical SMILES: O=Cc1cnc2n1CCc1c(C2=C2CCN(CC2)C)cccc1
isomeric SMILES: O=Cc1cnc2n1CCc1c(C2=C2CCN(CC2)C)cccc1
in ch i key: MWTBKTRZPHJQLH-UHFFFAOYSA-N
in ch i: InChI=1S/C19H21N3O/c1-21-9-6-15(7-10-21)18-17-5-3-2-4-14(17)8-11-22-16(13-23)12-20-19(18)22/h2-5,12-13H,6-11H2,1H3
comment: Alcaftadine is an antihistamine drug.
iupac name: 11-(1-methylpiperidin-4-ylidene)-5,6-dihydroimidazo[2,3-b][3]benzazepine-3-carbaldehyde
xref: CHEMBL1201747
synonym: R-89674
synonym: Lastacaft®
approved: t
ligand name: alcaftadine
type: SyntheticOrganicLigand

mavoglurant
canonical SMILES: COC(=O)N1CCC2C1CCCC2(O)C#Cc1cccc(c1)C
isomeric SMILES: COC(=O)N1CC[C@@H]2[C@H]1CCC[C@@]2(O)C#Cc1cccc(c1)C
in ch i key: ZFPZEYHRWGMJCV-ZHALLVOQSA-N
in ch i: InChI=1S/C19H23NO3/c1-14-5-3-6-15(13-14)8-11-19(22)10-4-7-17-16(19)9-12-20(17)18(21)23-2/h3,5-6,13,16-17,22H,4,7,9-10,12H2,1-2H3/t16-,17-,19-/m1/s1
iupac name: methyl (3aR,4S,7aR)-4-hydroxy-4-[2-(3-methylphenyl)ethynyl]-3,3a,5,6,7,7a-hexahydro-2H-indole-1-carboxylate
xref: CHEMBL3087515
synonym: AFQ-056
approved: f
ligand name: mavoglurant
type: SyntheticOrganicLigand

BETP
in ch i key: NTDFYGSSDDMNHI-UHFFFAOYSA-N
iupac name: 2-ethylsulfinyl-4-(3-phenylmethoxyphenyl)-6-(trifluoromethyl)pyrimidine
approved: f
ligand name: BETP
type: SyntheticOrganicLigand

NVP-BBT594
in ch i key: VQLNKQZLPGLOSI-UHFFFAOYSA-N
in ch i: InChI=1S/C28H30F3N7O3/c1-18(39)34-25-15-26(33-17-32-25)41-22-5-6-24-19(13-22)7-8-38(24)27(40)35-21-4-3-20(23(14-21)28(29,30)31)16-37-11-9-36(2)10-12-37/h3-6,13-15,17H,7-12,16H2,1-2H3,(H,35,40)(H,32,33,34,39)
iupac name: 5-(6-acetamidopyrimidin-4-yl)oxy-N-[4-[(4-methylpiperazin-1-yl)methyl]-3-(trifluoromethyl)phenyl]-2,3-dihydroindole-1-carboxamide
approved: f
ligand name: NVP-BBT594
type: SyntheticOrganicLigand

iodocyanopindolol
canonical SMILES: OC(COc1cccc2c1c(I)c([nH]2)C#N)CNC(C)C
isomeric SMILES: OC(COc1cccc2c1c(I)c([nH]2)C#N)CNC(C)C
in ch i key: WGSPBWSPJOBKNT-UHFFFAOYSA-N
in ch i: InChI=1S/C15H18IN3O2/c1-9(2)18-7-10(20)8-21-13-5-3-4-11-14(13)15(16)12(6-17)19-11/h3-5,9-10,18-20H,7-8H2,1-2H3
iupac name: 4-[2-hydroxy-3-(propan-2-ylamino)propoxy]-3-iodo-1H-indole-2-carbonitrile
approved: f
ligand name: iodocyanopindolol
type: SyntheticOrganicLigand

carmoterol
in ch i key: IHOXNOQMRZISPV-YJYMSZOUSA-N
in ch i: InChI=1S/C21H24N2O4/c1-13(11-14-3-5-15(27-2)6-4-14)22-12-19(25)16-7-9-18(24)21-17(16)8-10-20(26)23-21/h3-10,13,19,22,24-25H,11-12H2,1-2H3,(H,23,26)/t13-,19+/m1/s1
iupac name: 8-hydroxy-5-[(1R)-1-hydroxy-2-[[(2R)-1-(4-methoxyphenyl)propan-2-yl]amino]ethyl]-1H-quinolin-2-one
xref: CHEMBL1094785
approved: f
ligand name: carmoterol
type: SyntheticOrganicLigand

(S)-crizotinib
in ch i key: KTEIFNKAUNYNJU-LBPRGKRZSA-N
comment: Inhibition of MTH1 (gene symbol NUDT1) by (S)-crizotinib has revealed small molecule MTH1 inhibitors as a promising new class of anticancer compounds.
iupac name: 3-[(1S)-1-(2,6-dichloro-3-fluorophenyl)ethoxy]-5-(1-piperidin-4-ylpyrazol-4-yl)pyridin-2-amine
xref: CHEMBL1825141
synonym: ent-crizotinib
approved: f
ligand name: (S)-crizotinib
type: SyntheticOrganicLigand

compound 13k [PMID: 22390415]
in ch i key: DTXBFSJBRGLOHO-UHFFFAOYSA-N
in ch i: InChI=1S/C15H20N2O7P2/c1-10(2)24-13-5-3-11(4-6-13)12-7-8-16-14(9-12)17-15(25(18,19)20)26(21,22)23/h3-10,15H,1-2H3,(H,16,17)(H2,18,19,20)(H2,21,22,23)
iupac name: [phosphono-[[4-(4-propan-2-yloxyphenyl)pyridin-2-yl]amino]methyl]phosphonic acid
xref: CHEMBL2048241
approved: f
ligand name: compound 13k [PMID: 22390415]
type: SyntheticOrganicLigand

compound 15a [PMID: 22464687]
in ch i key: MSSQOQPKGAMUSY-LEAFIULHSA-N
in ch i: InChI=1S/C29H31ClN2O6/c1-36-24-7-3-5-20(29(24)37-2)28-21-16-19(30)8-9-22(21)32-12-4-6-23(32)25(38-28)17-26(33)31-13-10-18(11-14-31)15-27(34)35/h3-9,12,16,18,25,28H,10-11,13-15,17H2,1-2H3,(H,34,35)/t25-,28-/m1/s1
iupac name: 2-[1-[2-[(4R,6S)-8-chloro-6-(2,3-dimethoxyphenyl)-4,6-dihydropyrrolo[1,2-a][4,1]benzoxazepin-4-yl]acetyl]piperidin-4-yl]acetic acid
xref: CHEMBL2057280
approved: f
ligand name: compound 15a [PMID: 22464687]
type: SyntheticOrganicLigand

edoxaban
in ch i key: HGVDHZBSSITLCT-JLJPHGGASA-N
comment: Edoxaban is an oral, once-daily factor Xa inhibitor anticoagulant. Marketed formulations contain edoxaban tosylate (PubChem CID 44610678).
iupac name: N'-(5-chloropyridin-2-yl)-N-[(1S,2R,4S)-4-(dimethylcarbamoyl)-2-[(5-methyl6,7-dihydro-4H-[1,3]thiazolo[5,4-c]pyridine-2-carbonyl)amino]cyclohexyl]oxamide
xref: CHEMBL1269025
synonym: Savaysa®
synonym: DU-176
synonym: edoxaban tosylate
synonym: DU-176b
synonym: Lixiana®
approved: t
ligand name: edoxaban
type: SyntheticOrganicLigand

omaveloxolone
in ch i key: RJCWBNBKOKFWNY-IDPLTSGASA-N
in ch i: InChI=1S/C33H44F2N2O3/c1-27(2)11-13-33(37-26(40)32(8,34)35)14-12-31(7)24(20(33)17-27)21(38)15-23-29(5)16-19(18-36)25(39)28(3,4)22(29)9-10-30(23,31)6/h15-16,20,22,24H,9-14,17H2,1-8H3,(H,37,40)/t20-,22-,24-,29-,30+,31+,33-/m0/s1
comment: Chemically omaveloxolone (RTA 408) is a second generation synthetic oleanane triterpenoid compound, which structurally resembles <Ligand id=2717/>, and has difluoropropanamide replacing the carboxylic acid moiety. This compound is claimed in patent WO2013163344A1. The chemical structure represented above, was drawn from this patent, but structures with alternate stereochemistry are submitted in PubChem.
iupac name: N-[(4aS,6aR,6bS,8aR,12aS,14aR,14bS)-11-cyano-2,2,6a,6b,9,9,12a-heptamethyl-10,14-dioxo-1,3,4,5,6,7,8,8a,14a,14b-decahydropicen-4a-yl]-2,2-difluoropropanamide
synonym: RTA-408
synonym: RTA 408
approved: f
ligand name: omaveloxolone
type: SyntheticOrganicLigand

insulin glargine
in ch i key: COCFEDIXXNGUNL-RFKWWTKHSA-N
comment: Insulin glargine is a recombinant, modified analogue of human insulin. The chemical structure shown here was generated using the SMILES from PubChem CID 44146714. A number of insulin glargine biosimilars have been approved internationally since the expiration of patents on Lantus® in 2014: a comprehensive list that is maintained by the Generics and Biosimilar Initiative (https://www.gabionline.net) is available here. The first fully interchangeable biosimilar to be FDA approved was Semglee® (insulin glargine-yfgn; Mylan Pharmaceuticals), in July 2021.
xref: CHEMBL1201497
synonym: Toujeo®
synonym: HOE-901
synonym: HOE901
synonym: Optisulin
synonym: Lantus®
approved: t
ligand name: insulin glargine
type: PeptideLigand

benzamidine
canonical SMILES: NC(=N)c1ccccc1
isomeric SMILES: NC(=N)c1ccccc1
in ch i key: PXXJHWLDUBFPOL-UHFFFAOYSA-N
in ch i: InChI=1S/C7H8N2/c8-7(9)6-4-2-1-3-5-6/h1-5H,(H3,8,9)
iupac name: Benzenecarboximidamide
xref: CHEMBL20936
approved: f
ligand name: benzamidine
type: SyntheticOrganicLigand

amfenac
canonical SMILES: OC(=O)Cc1cccc(c1N)C(=O)c1ccccc1
isomeric SMILES: OC(=O)Cc1cccc(c1N)C(=O)c1ccccc1
in ch i key: SOYCMDCMZDHQFP-UHFFFAOYSA-N
in ch i: InChI=1S/C15H13NO3/c16-14-11(9-13(17)18)7-4-8-12(14)15(19)10-5-2-1-3-6-10/h1-8H,9,16H2,(H,17,18)
comment: Amfenac is the active metabolite of nepafenac. It is a potent non-steroidal antiinflammatory drug (NSAID) <Reference id=24748/>. Marketed formulations may contain amfenac sodium (PubChem CID 23665728).
iupac name: 2-[2-amino-3-(benzoyl)phenyl]acetic acid
xref: CHEMBL25146
synonym: AHR-5850D
synonym: Fenazox® (Japan)
approved: t
ligand name: amfenac
type: SyntheticOrganicLigand

methylnaltrexone
canonical SMILES: O=C1CCC2(C34C1Oc1c4c(CC2[N+](CC3)(C)CC2CC2)ccc1O)O
in ch i key: JVLBPIPGETUEET-GAAHOAFPSA-O
in ch i: InChI=1S/C21H25NO4/c1-22(11-12-2-3-12)9-8-20-17-13-4-5-14(23)18(17)26-19(20)15(24)6-7-21(20,25)16(22)10-13/h4-5,12,16,19,25H,2-3,6-11H2,1H3/p+1/t16-,19+,20+,21-,22?/m1/s1
comment: The charged tetravalent nitrogen atom in this molecule reduces its ability to cross the blood-brain barrier, thereby restricting its activity to peripheral targets. This type of peripherally acting mu-opioid receptor antagonist is known by the acronym PAMORA.
iupac name: (4R,4aS,7aR,12bS)-3-(cyclopropylmethyl)-4a,9-dihydroxy-3-methyl-2,4,5,6,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinoline-3-ium-7-one
xref: CHEMBL1186579
synonym: MRZ-2663BR
synonym: Relistor®
approved: t
ligand name: methylnaltrexone
type: SyntheticOrganicLigand

prasugrel
in ch i key: DTGLZDAWLRGWQN-UHFFFAOYSA-N
in ch i: InChI=1S/C20H20FNO3S/c1-12(23)25-18-10-14-11-22(9-8-17(14)26-18)19(20(24)13-6-7-13)15-4-2-3-5-16(15)21/h2-5,10,13,19H,6-9,11H2,1H3
comment: This drug is metabolised to its active metabolite R-138727. Marketed formulations may contain prasugrel hydrochloride (PubChem CID 10158453).
iupac name: [5-[2-cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl]-6,7-dihydro-4H-thieno[4,5-c]pyridin-2-yl] acetate
xref: CHEMBL1201772
synonym: CS-747
synonym: Effient®
synonym: Efient®
approved: t
ligand name: prasugrel
type: SyntheticOrganicLigand

gabapentin enacarbil
in ch i key: TZDUHAJSIBHXDL-UHFFFAOYSA-N
in ch i: InChI=1S/C16H27NO6/c1-11(2)14(20)22-12(3)23-15(21)17-10-16(9-13(18)19)7-5-4-6-8-16/h11-12H,4-10H2,1-3H3,(H,17,21)(H,18,19)
comment: Gabapentin enacarbil is a prodrug of gabapentin. It exhibits increased bioavailability compared to gabapentin.
iupac name: 2-[1-[[1-(2-methylpropanoyloxy)ethoxycarbonylamino]methyl]cyclohexyl]acetic acid
xref: CHEMBL1628502
synonym: XP-13512
synonym: Horizant®
synonym: Regnite®
approved: t
ligand name: gabapentin enacarbil
type: SyntheticOrganicLigand

zuclopenthixol
in ch i key: WFPIAZLQTJBIFN-DVZOWYKESA-N
in ch i: InChI=1S/C22H25ClN2OS/c23-17-7-8-22-20(16-17)18(19-4-1-2-6-21(19)27-22)5-3-9-24-10-12-25(13-11-24)14-15-26/h1-2,4-8,16,26H,3,9-15H2/b18-5-
comment: Zuclopenthixol is a thioxanthene class typical antipsychotic. Chemically it is the cis-isomer of clopenthixol. The CAS registry number (53772-83-1) submitted with the WHO INN record for zuclopenthixol maps to PubChem CID 5311507.
iupac name: 2-[4-[(3Z)-3-(2-chlorothioxanthen-9-ylidene)propyl]piperazin-1-yl]ethanol
xref: CHEMBL53904
synonym: Cisordinol®
synonym: Acuphase®
synonym: NSC 64087
synonym: NSC169185
synonym: cis(Z)-cloflupentixol
synonym: Clopixol®
approved: t
ligand name: zuclopenthixol
type: SyntheticOrganicLigand

tianeptine
in ch i key: JICJBGPOMZQUBB-UHFFFAOYSA-N
comment: Chemically tianeptine can be classified as a tricyclic antidepressant (TCA), but evidence suggests that it has a quite different pharmacological mechanism of action compared to typical TCAs <Reference id=31258/><Reference id=24728/><Reference id=31259/>.
iupac name: 7-[(3-chloro-6-methyl-5,5-dioxo-11H-benzo[c][2,1]benzothiazepin-11-yl)amino]heptanoic acid
xref: CHEMBL1289110
synonym: Coaxil
synonym: Tatinol
synonym: Tianeurax
synonym: Stablon®
synonym: tianeptine sodium
approved: t
ligand name: tianeptine
type: SyntheticOrganicLigand

pipotiazine
in ch i key: JOMHSQGEWSNUKU-UHFFFAOYSA-N
in ch i: InChI=1S/C24H33N3O3S2/c1-25(2)32(29,30)20-8-9-24-22(18-20)27(21-6-3-4-7-23(21)31-24)14-5-13-26-15-10-19(11-16-26)12-17-28/h3-4,6-9,18-19,28H,5,10-17H2,1-2H3
comment: Pipotiazine is a phenothiazine class typical antipsychotic.
iupac name: 10-[3-[4-(2-hydroxyethyl)piperidin-1-yl]propyl]-N,N-dimethylphenothiazine-2-sulfonamide
xref: CHEMBL398880
synonym: pipothiazine
synonym: Piportil®
approved: t
ligand name: pipotiazine
type: SyntheticOrganicLigand

perospirone
in ch i key: FBVFZWUMDDXLLG-HDICACEKSA-N
in ch i: InChI=1S/C23H30N4O2S/c28-22-17-7-1-2-8-18(17)23(29)27(22)12-6-5-11-25-13-15-26(16-14-25)21-19-9-3-4-10-20(19)30-24-21/h3-4,9-10,17-18H,1-2,5-8,11-16H2/t17-,18+
comment: Perospirone is an azapirone class atypical (second generation) antipsychotic. A higher incidence of extrapyramidal side-effects is associated with perospirone use than with other atypical antipsychotics, but fewer than reported with typical (first generation) antipsychotics.
iupac name: (3aS,7aR)-2-[4-[4-(1,2-benzothiazol-3-yl)piperazin-1-yl]butyl]-3a,4,5,6,7,7a-hexahydroisoindole-1,3-dione
xref: CHEMBL1472975
synonym: Lullan® (Japan)
approved: t
ligand name: perospirone
type: SyntheticOrganicLigand

selexipag
in ch i key: QXWZQTURMXZVHJ-UHFFFAOYSA-N
in ch i: InChI=1S/C26H32N4O4S/c1-20(2)30(16-10-11-17-34-19-24(31)29-35(3,32)33)23-18-27-25(21-12-6-4-7-13-21)26(28-23)22-14-8-5-9-15-22/h4-9,12-15,18,20H,10-11,16-17,19H2,1-3H3,(H,29,31)
comment: Selexipag represents a first-in-class selective, long-acting, oral prostacyclin IP receptor agonist. This compound is a prodrug, with the active molecule being <Ligand id=5852/>.
iupac name: 2-[4-[[5,6-di(phenyl)pyrazin-2-yl]-propan-2-ylamino]butoxy]-N-methylsulfonylacetamide
xref: CHEMBL238804
synonym: Uptravi®
synonym: NS 304
synonym: NS-304
synonym: ACT-293987
approved: t
ligand name: selexipag
type: SyntheticOrganicLigand

lofepramine
in ch i key: SAPNXPWPAUFAJU-UHFFFAOYSA-N
in ch i: InChI=1S/C26H27ClN2O/c1-28(19-26(30)22-13-15-23(27)16-14-22)17-6-18-29-24-9-4-2-7-20(24)11-12-21-8-3-5-10-25(21)29/h2-5,7-10,13-16H,6,11-12,17-19H2,1H3
comment: Marketed formulations may contain lofepramine hydrochloride (PubChem CID 33611).
iupac name: 1-(4-chlorophenyl)-2-[3-(5,6-dihydrobenzo[b][1]benzazepin-11-yl)propyl-methylamino]ethanone
xref: CHEMBL87708
synonym: WHR-2908A
synonym: Emdalen
synonym: Lomont ®
synonym: Gamanil ®
synonym: Tymelyt ®
approved: t
ligand name: lofepramine
type: SyntheticOrganicLigand

bitopertin
in ch i key: YUUGYIUSCYNSQR-LBPRGKRZSA-N
comment: Bitopertin is a non-competitive glycine transporter 1 (GlyT1) inhibitor (functionally a glycine reuptake inhibitor) that was developed by Roche as a potential anti-schizophrenia drug. Its chemical structure is represented in ChEMBL by the R-isomer, CHEMBL1169880.
iupac name: [4-[3-fluoro-5-(trifluoromethyl)pyridin-2-yl]piperazin-1-yl]-[5-methylsulfonyl-2-[(2S)-1,1,1-trifluoropropan-2-yl]oxyphenyl]methanone
synonym: RG1678
synonym: paliflutine
synonym: RO-4917838
approved: f
ligand name: bitopertin
type: SyntheticOrganicLigand

N-desalkylquetiapine
canonical SMILES: N1CCN(CC1)C1=Nc2ccccc2Sc2c1cccc2
isomeric SMILES: N1CCN(CC1)C1=Nc2ccccc2Sc2c1cccc2
in ch i key: JLOAJISUHPIQOX-UHFFFAOYSA-N
in ch i: InChI=1S/C17H17N3S/c1-3-7-15-13(5-1)17(20-11-9-18-10-12-20)19-14-6-2-4-8-16(14)21-15/h1-8,18H,9-12H2
comment: N-desalkylquetiapine is an active metabolite of the antidepressant <Ligand id=50/>. N-desalkylquetiapine is approximately 100-fold more potent than quetiapine in inhibition of the norepinephrine reuptake transporter (NET) <Reference id=24695/><Reference id=24702/>. This acts to increase dopamine levels in the frontal cortex and adds to the compound's antidepressant effect <Reference id=24695/><Reference id=24703/>.
iupac name: 6-piperazin-1-ylbenzo[b][1,5]benzothiazepine
synonym: norquetiapine
approved: f
ligand name: N-desalkylquetiapine
type: SyntheticOrganicLigand

pixantrone
canonical SMILES: NCCNc1ccc(c2c1C(=O)c1cnccc1C2=O)NCCN
isomeric SMILES: NCCNc1ccc(c2c1C(=O)c1cnccc1C2=O)NCCN
in ch i key: PEZPMAYDXJQYRV-UHFFFAOYSA-N
in ch i: InChI=1S/C17H19N5O2/c18-4-7-21-12-1-2-13(22-8-5-19)15-14(12)16(23)10-3-6-20-9-11(10)17(15)24/h1-3,6,9,21-22H,4-5,7-8,18-19H2
comment: Pixantrone is an antineoplastic drug that also shows immunosuppressant activity <Reference id=24689/><Reference id=24690/>. It is administered clinically as pixantrone dimaleate (PubChem CID: 9937618).
iupac name: 6,9-bis(2-aminoethylamino)benzo[g]isoquinoline-5,10-dione
xref: CHEMBL167731
synonym: Pixuvri®
synonym: BBR-2778
approved: t
ligand name: pixantrone
type: SyntheticOrganicLigand

olodaterol
in ch i key: COUYJEVMBVSIHV-SFHVURJKSA-N
in ch i: InChI=1S/C21H26N2O5/c1-21(2,10-13-4-6-15(27-3)7-5-13)22-11-18(25)16-8-14(24)9-17-20(16)28-12-19(26)23-17/h4-9,18,22,24-25H,10-12H2,1-3H3,(H,23,26)/t18-/m0/s1
comment: Marketed formulations may contain olodaterol hydrochloride (PubChem CID 11711522).
iupac name: 6-hydroxy-8-[(1R)-1-hydroxy-2-[[1-(4-methoxyphenyl)-2-methylpropan-2-yl]amino]ethyl]-4H-1,4-benzoxazin-3-one
xref: CHEMBL605846
synonym: BI-1744
synonym: BI-1744-CL
synonym: Striverdi®
approved: t
ligand name: olodaterol
type: SyntheticOrganicLigand

lasofoxifene
in ch i key: GXESHMAMLJKROZ-IAPPQJPRSA-N
in ch i: InChI=1S/C28H31NO2/c30-24-11-15-27-23(20-24)10-14-26(21-6-2-1-3-7-21)28(27)22-8-12-25(13-9-22)31-19-18-29-16-4-5-17-29/h1-3,6-9,11-13,15,20,26,28,30H,4-5,10,14,16-19H2/t26-,28+/m1/s1
iupac name: (5R,6S)-6-phenyl-5-[4-(2-pyrrolidin-1-ylethoxy)phenyl]-5,6,7,8-tetrahydronaphthalen-2-ol
xref: CHEMBL328190
synonym: Fablyn
synonym: Oporia
synonym: lasofoxifene tartrate
approved: f
ligand name: lasofoxifene
type: SyntheticOrganicLigand

quisinostat
in ch i key: PAWIYAYFNXQGAP-UHFFFAOYSA-N
in ch i: InChI=1S/C21H26N6O2/c1-26-14-17(18-4-2-3-5-19(18)26)11-22-10-15-6-8-27(9-7-15)21-23-12-16(13-24-21)20(28)25-29/h2-5,12-15,22,29H,6-11H2,1H3,(H,25,28)
comment: Quisinostat is an HDAC inhibitor. The compound has highest potency for HDAC1 and modest potency with HDACs 2, 4, 10, and 11. Quisinostat exhibits >30-fold selectivity against HDACs 3, 5, 8, and 9, with lowest potency for HDACs 6 and 7 <Reference id=24594/>. The compound also has antimalarial activity <Reference id=43239/>. The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
iupac name: N-hydroxy-2-[4-[[(1-methylindol-3-yl)methylamino]methyl]piperidin-1-yl]pyrimidine-5-carboxamide
xref: CHEMBL2105763
synonym: JNJ-26481585
approved: f
ligand name: quisinostat
type: SyntheticOrganicLigand

naloxegol
in ch i key: XNKCCCKFOQNXKV-ZRSCBOBOSA-N
in ch i: InChI=1S/C34H53NO11/c1-3-9-35-10-8-33-30-26-4-5-27(36)31(30)46-32(33)28(6-7-34(33,37)29(35)25-26)45-24-23-44-22-21-43-20-19-42-18-17-41-16-15-40-14-13-39-12-11-38-2/h3-5,28-29,32,36-37H,1,6-25H2,2H3/t28-,29+,32-,33-,34+/m0/s1
comment: Naloxegol is a PEGylated version of naloxol (α-naloxol PubChem CID 5492271; β-naloxol PubChem CID 5492293). PEGylation reduces the compound's ability to cross the blood-brain barrier, therefore restricting CNS penetration. Naloxegol is termed a peripherally acting μ-opioid receptor antagonist, or PAMORA. The synonyms suffixed with %22oxalate %22 map to the salt as PubChem CID 56959086
xref: CHEMBL2219418
synonym: Movantik®
synonym: AZ-13337019
synonym: AZ13337019
synonym: Moventig®
synonym: NKTR-118
approved: t
ligand name: naloxegol
type: SyntheticOrganicLigand

JNJ-47965567
in ch i key: XREFXUCWSYMIOG-UHFFFAOYSA-N
in ch i: InChI=1S/C28H32N4O2S/c33-26(25-12-7-15-29-27(25)35-24-10-5-2-6-11-24)30-22-28(13-20-34-21-14-28)32-18-16-31(17-19-32)23-8-3-1-4-9-23/h1-12,15H,13-14,16-22H2,(H,30,33)
comment: JNJ-479655 is a centrally acting, selective P2X7 antagonist. The enhanced brain to plasma ratio achieved by this compound boosts its utility as a tool to understand the role of P2X7 in CNS models of pathophysiology <Reference id=24666/>.
iupac name: N-[[4-(4-phenylpiperazin-1-yl)oxan-4-yl]methyl]-2-phenylsulfanylpyridine-3-carboxamide
xref: CHEMBL2338352
synonym: JNJ-479655
synonym: JNJ47965567
approved: f
ligand name: JNJ-47965567
type: SyntheticOrganicLigand

norzotepine
canonical SMILES: CNCCOC1=Cc2ccccc2Sc2c1cc(Cl)cc2
isomeric SMILES: CNCCOC1=Cc2ccccc2Sc2c1cc(Cl)cc2
in ch i key: OVVBIIBBRZVPAL-UHFFFAOYSA-N
in ch i: InChI=1S/C17H16ClNOS/c1-19-8-9-20-15-10-12-4-2-3-5-16(12)21-17-7-6-13(18)11-14(15)17/h2-7,10-11,19H,8-9H2,1H3
comment: Norzotepine is a major active metabolite of the drug <Ligand id=103/> <Reference id=24665/>. Norzotepine acts as a norepinephrine reuptake inhibitor and exhibits anti-depressant and anti-psychotic activity in animal studies <Reference id=24665/>.
iupac name: 2-(8-chlorobenzo[b][1]benzothiepin-6-yl)oxy-N-methylethanamine
approved: f
ligand name: norzotepine
type: SyntheticOrganicLigand

eliglustat
in ch i key: FJZZPCZKBUKGGU-AUSIDOKSSA-N
in ch i: InChI=1S/C23H36N2O4/c1-2-3-4-5-6-9-22(26)24-19(17-25-12-7-8-13-25)23(27)18-10-11-20-21(16-18)29-15-14-28-20/h10-11,16,19,23,27H,2-9,12-15,17H2,1H3,(H,24,26)/t19-,23-/m1/s1
comment: The marketed formulation contains eliglustat tartrate (PubChem CID 52918379).
iupac name: N-[(1R,2R)-1-(2,3-dihydro-1,4-benzodioxin-7-yl)-1-hydroxy-3-pyrrolidin-1-ylpropan-2-yl]octanamide
xref: CHEMBL2110588
synonym: Cerdelga®
synonym: GENZ-112638
approved: t
ligand name: eliglustat
type: SyntheticOrganicLigand

cobicistat
in ch i key: ZCIGNRJZKPOIKD-CQXVEOKZSA-N
in ch i: InChI=1S/C40H53N7O5S2/c1-29(2)38-43-34(27-53-38)25-46(3)39(49)45-36(16-17-47-18-20-51-21-19-47)37(48)42-32(22-30-10-6-4-7-11-30)14-15-33(23-31-12-8-5-9-13-31)44-40(50)52-26-35-24-41-28-54-35/h4-13,24,27-29,32-33,36H,14-23,25-26H2,1-3H3,(H,42,48)(H,44,50)(H,45,49)/t32-,33-,36+/m1/s1
comment: This compound is approved as a component of the so-called 'Quad pill' (Stribild®), an anti-HIV therapy which contains cobicistat, elvitegravir, <Ligand id=11244/>, and <Ligand id=10948/>.
iupac name: 1,3-thiazol-5-ylmethyl N-[(2R,5R)-5-[[(2S)-2-[[methyl-[(2-propan-2-yl-1,3-thiazol-4-yl)methyl]carbamoyl]amino]-4-morpholin-4-ylbutanoyl]amino]-1,6-diphenylhexan-2-yl]carbamate
xref: CHEMBL2095208
synonym: Stribild
synonym: GS-9350
synonym: Tybost®
approved: t
ligand name: cobicistat
type: SyntheticOrganicLigand

lifitegrast
in ch i key: JFOZKMSJYSPYLN-QHCPKHFHSA-N
comment: It is postulated that lifitegrast (SAR 1118) interacts with the lymphocyte function-associated antigen-1 (LFA-1) to inhbit the LFA-1/ICAM-1 adhesion interaction and was approved for the treatment of Dry Ey in 2016 <Reference id=24643/><Reference id=31379/>. LFA-1 is a heterodimeric member of the β2 integrin family which is essential for adhesion, migration, and proliferation of T cells at sites of inflammation, and is involved in T cell specific immune responses through the formation of adhesive interactions and immunological synapses. Intercellular adhesion molecule‑1 (ICAM‑1) is the cognate ligand of LFA-1.The compound formulation is claimed in patent WO2014100135 <Reference id=31379/>.
iupac name: (2S)-2-[[2-(1-benzofuran-6-carbonyl)-5,7-dichloro3,4-dihydro-1H-isoquinoline-6-carbonyl]amino]-3-(3-methylsulfonylphenyl)propanoic acid
xref: CHEMBL2048028
synonym: Xiidra®
synonym: compound 1g [PMID: 24900456]
synonym: SAR-1118-023
synonym: SAR-1118
synonym: SAR 1118
approved: t
ligand name: lifitegrast
type: SyntheticOrganicLigand

pirfenidone
canonical SMILES: Cc1ccc(=O)n(c1)c1ccccc1
isomeric SMILES: Cc1ccc(=O)n(c1)c1ccccc1
in ch i key: ISWRGOKTTBVCFA-UHFFFAOYSA-N
in ch i: InChI=1S/C12H11NO/c1-10-7-8-12(14)13(9-10)11-5-3-2-4-6-11/h2-9H,1H3
comment: Pirfenidone is an anti-fibrotic drug. In addition to its proven anti-fibrotic effects in lung tissue, pirfenidone-induced in vitro and in vivo anti-fibrotic activity has been reported in experimental liver and renal fibrosis <Reference id=31254/><Reference id=31255/>. SARS-CoV-2: COVID-19 is accompanied by inflammation and fibrotic lung damage that appears to persist beyond immediate recovery. The clinical potential for applying the antifibrotic activity of pirfenidone to help treat COVID-19-related pulmonary fibrosis is reviewed by Ferrara et al. (2020) <Reference id=39836/>.
iupac name: 5-methyl-1-phenylpyridin-2-one
xref: CHEMBL1256391
synonym: AMR-69
synonym: Esbriet®
synonym: Pirespa
synonym: Etuary
approved: t
ligand name: pirfenidone
type: SyntheticOrganicLigand

compound 7 [PMID: 24825313]
in ch i key: BPMOENJVOOOATO-UHFFFAOYSA-N
in ch i: InChI=1S/C22H24N2O4/c1-28-19-8-9-21-20(13-19)16(14-24-21)10-11-23-22(27)12-18(26)7-4-15-2-5-17(25)6-3-15/h2-3,5-6,8-9,13-14,24-25H,4,7,10-12H2,1H3,(H,23,27)
comment: This is an investigational Alzheimer's disease (AD) compound. Chemically, it is a hybrid of <Ligand id=7000/> and <Ligand id=224/> <Reference id=24639/>, two compounds which have previously shown some benefit in AD research. The hybrid molecule is brain-penetrant. In in vitro experiments, compound 7 exhibits significant neuroprotective activity in AD model cells <Reference id=24639/>. The ChemSpider ID is 30922431.
iupac name: 5-(4-Hydroxyphenyl)-N-[2-(5-methoxy-1H-indol-3-yl)ethyl]-3-oxopentanamide
approved: f
ligand name: compound 7 [PMID: 24825313]
type: SyntheticOrganicLigand

2-PMAP
canonical SMILES: Oc1ccccc1NCc1ccccn1
isomeric SMILES: Oc1ccccc1NCc1ccccn1
in ch i key: GXJRVWZNMZGWAQ-UHFFFAOYSA-N
in ch i: InChI=1S/C12H12N2O/c15-12-7-2-1-6-11(12)14-9-10-5-3-4-8-13-10/h1-8,14-15H,9H2
comment: 2-PMAP is an investigational compound for Alzheimer's disease (AD). A recent study has demonstrated that this compound crosses the blood-brain barrier and reduces levels of full-length amyloid precursor protein (APP) and amyloid beta (Aβ) deposition in the brains of AD model mice without causing significant toxicity <Reference id=24638/>. This is accompanied by reduced Aβ pathology and rescue of memory deficit in AD model mice via an inhibitory effect on mRNA translation. This compound may exist as a tautomer with PubChem CID 68604369.
iupac name: 2-(pyridin-2-ylmethylamino)phenol
synonym: AGN-PC-0031SD
synonym: ARN-2966
approved: f
ligand name: 2-PMAP
type: SyntheticOrganicLigand

SGC-CBP30
in ch i key: GEPYBHCJBORHCE-SFHVURJKSA-N
in ch i: InChI=1S/C28H33ClN4O3/c1-18(32-11-13-35-14-12-32)17-33-25-8-7-22(28-19(2)31-36-20(28)3)16-24(25)30-27(33)10-6-21-5-9-26(34-4)23(29)15-21/h5,7-9,15-16,18H,6,10-14,17H2,1-4H3/t18-/m0/s1
comment: CBP30 targets the CBP/p300 bromodomain, with much improved selectivity compared to the pan-BET bromodomain inhibitor <Ligand id=7511/> <Reference id=30729/>. CBP30 has therapeutic potential against autoimmune diseases characterised by aberrant Th17 responses. This is a compound from the Structural Genomics Consortium's (SGC) Epigenetics Probes Collection. The compound also has antimalarial activity. The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
iupac name: 2-[2-(3-chloro-4-methoxyphenyl)ethyl]-5-(dimethyl-1,2-oxazol-4-yl)-1-[(2S)-2-(morpholin-4-yl)propyl]-1H-1,3-benzodiazole
approved: f
ligand name: SGC-CBP30
type: SyntheticOrganicLigand

compound 15 [Hay et al., 2013]
canonical SMILES: Cc1onc(c1c1ccc2c(c1)C(O)(CC2)c1ccccc1)C
isomeric SMILES: Cc1onc(c1c1ccc2c(c1)C(O)(CC2)c1ccccc1)C
in ch i key: SEOJJNHYXOQNOZ-UHFFFAOYSA-N
in ch i: InChI=1S/C20H19NO2/c1-13-19(14(2)23-21-13)16-9-8-15-10-11-20(22,18(15)12-16)17-6-4-3-5-7-17/h3-9,12,22H,10-11H2,1-2H3
comment: The reference for the discovery of this compound is <Reference id=24628/>.
iupac name: 6-(dimethyl-1,2-oxazol-4-yl)-1-phenyl-2,3-dihydro-1H-inden-1-ol
xref: CHEMBL3220860
approved: f
ligand name: compound 15 [Hay et al., 2013]
type: SyntheticOrganicLigand

isoxazole azepine compound 3
in ch i key: DRSQZZRFHBWKKZ-AWEZNQCLSA-N
xref: CHEMBL2431090
approved: f
ligand name: isoxazole azepine compound 3
type: SyntheticOrganicLigand

XD1
in ch i key: PRGILOMAMBLWNG-HNNXBMFYSA-N
in ch i: InChI=1S/C21H23NO6/c1-11(23)22-15-7-5-12-9-18(26-2)20(27-3)21(28-4)19(12)13-6-8-16(24)17(25)10-14(13)15/h6,8-10,15H,5,7H2,1-4H3,(H,22,23)(H,24,25)/t15-/m0/s1
iupac name: N-[(7S)-10-hydroxy-1,2,3-trimethoxy-9-oxo-6,7-dihydro-5H-benzo[d]heptalen-7-yl]acetamide
xref: CHEMBL142588
synonym: colchicein
synonym: colchiceine
synonym: NSC33411
approved: f
ligand name: XD1
type: SyntheticOrganicLigand

XD14
in ch i key: DPBKLIVPNYGQQG-UHFFFAOYSA-N
in ch i: InChI=1S/C20H27N3O5S/c1-6-15-18(13(5)24)12(4)21-19(15)20(26)22-16-11-14(9-10-17(16)25)29(27,28)23(7-2)8-3/h9-11,21,25H,6-8H2,1-5H3,(H,22,26)
iupac name: 4-acetyl-N-[5-(diethylsulfamoyl)-2-hydroxyphenyl]-3-ethyl-5-methyl-1H-pyrrole-2-carboxamide
approved: f
ligand name: XD14
type: SyntheticOrganicLigand

PFI-1
in ch i key: TXZPMHLMPKIUGK-UHFFFAOYSA-N
in ch i: InChI=1S/C16H17N3O4S/c1-19-10-11-9-12(7-8-13(11)17-16(19)20)18-24(21,22)15-6-4-3-5-14(15)23-2/h3-9,18H,10H2,1-2H3,(H,17,20)
comment: This compound is an inhibitor of the bromodomain and extra-terminal (BET) proteins, BRD2-4 <Reference id=24622/>. This is a compound from the Structural Genomics Consortium's (SGC) Epigenetics Probes Collection.
iupac name: 2-methoxy-N-(3-methyl-2-oxo-1,2,3,4-tetrahydroquinazolin-6-yl)benzene-1-sulfonamide
xref: CHEMBL2179387
synonym: QCR-192
synonym: HY-16586
synonym: PF-6405761
approved: f
ligand name: PFI-1
type: SyntheticOrganicLigand

compound 38 [PMID: 24000170]
in ch i key: ZULXIHDLPPWDPC-UHFFFAOYSA-N
in ch i: InChI=1S/C23H20N4O3/c1-12-19(13(2)30-27-12)16-10-17-21(26-23(16)29-3)20-15(9-14-7-5-4-6-8-14)22(28)25-18(20)11-24-17/h4-8,10-11,15H,9H2,1-3H3,(H,25,28)
comment: This compound is an inhibitor of the bromodomain and extra-terminal (BET) proteins, BRD2-4 <Reference id=24621/>.
iupac name: 9-benzyl-3-(dimethyl-1,2-oxazol-4-yl)-2-methoxy-7H,8H,9H-pyrrolo[2,3-c]1,5-naphthyridin-8-one
approved: f
ligand name: compound 38 [PMID: 24000170]
type: SyntheticOrganicLigand

compound 36 [PMID: 24000170]
in ch i key: WWSIFGSLYORAET-UHFFFAOYSA-N
in ch i: InChI=1S/C23H17F3N4O4/c1-10-17(11(2)34-30-10)13-8-14-20(29-22(13)32-3)19-15(9-27-14)28-21(31)18(19)12-6-4-5-7-16(12)33-23(24,25)26/h4-9,18H,1-3H3,(H,28,31)
comment: This compound is an inhibitor of the bromodomain and extra-terminal (BET) proteins, BRD2-4 <Reference id=24621/>.
iupac name: 3-(dimethyl-1,2-oxazol-4-yl)-2-methoxy-9-[2-(trifluoromethoxy)phenyl]-7H,8H,9H-pyrrolo[2,3-c]1,5-naphthyridin-8-one
approved: f
ligand name: compound 36 [PMID: 24000170]
type: SyntheticOrganicLigand

R55
canonical SMILES: NC(=N)SCc1ccc(s1)CSC(=N)N
isomeric SMILES: NC(=N)SCc1ccc(s1)CSC(=N)N
in ch i key: XGDUNTSTRCLVLN-UHFFFAOYSA-N
in ch i: InChI=1S/C8H12N4S3/c9-7(10)13-3-5-1-2-6(15-5)4-14-8(11)12/h1-2H,3-4H2,(H3,9,10)(H3,11,12)
comment: R55 is an experimental compound with potential therapeutic implications for Alzheimer's disease <Reference id=24620/>.
iupac name: [5-(carbamimidoylsulfanylmethyl)thiophen-2-yl]methylsulfanylmethanimidamide
synonym: TPT-260
synonym: TPT260
synonym: compound 1 [PMID: 24747528]
approved: f
ligand name: R55
type: SyntheticOrganicLigand

olaparib
in ch i key: FDLYAMZZIXQODN-UHFFFAOYSA-N
in ch i: InChI=1S/C24H23FN4O3/c25-20-8-5-15(14-21-17-3-1-2-4-18(17)22(30)27-26-21)13-19(20)24(32)29-11-9-28(10-12-29)23(31)16-6-7-16/h1-5,8,13,16H,6-7,9-12,14H2,(H,27,30)
comment: Olaparib is an AstraZeneca poly ADP ribose polymerase (PARP) inhibitor <Reference id=24617/>. It is discussed in the AZ 2014 review paper <Reference id=26127/>. Cancer cells carrying BRCA mutations become more reliant on PARP activity to maintain DNA repair <Reference id=24616/>, so this enzyme represents a vulnerable target for pharmaceutical intervention in these cancers.
iupac name: 4-[[3-[4-(cyclopropanecarbonyl)piperazine-1-carbonyl]-4-fluorophenyl]methyl]-2H-phthalazin-1-one
xref: CHEMBL521686
synonym: Lynparza®
synonym: AZD-2281
synonym: AZD2281
approved: t
ligand name: olaparib
type: SyntheticOrganicLigand

I-BET151
in ch i key: VUVUVNZRUGEAHB-CYBMUJFWSA-N
in ch i: InChI=1S/C23H21N5O3/c1-12-21(14(3)31-27-12)16-9-18-15(10-20(16)30-4)22-19(11-25-18)26-23(29)28(22)13(2)17-7-5-6-8-24-17/h5-11,13H,1-4H3,(H,26,29)/t13-/m1/s1
comment: I-BET151 is a selective BET inhibitor for BRD2, BRD3 and BRD4 <Reference id=24612/><Reference id=24613/>.
iupac name: 7-(dimethyl-1,2-oxazol-4-yl)-8-methoxy-1-[(1R)-1-(pyridin-2-yl)ethyl]-1H,2H,3H-imidazo[4,5-c]quinolin-2-one
xref: CHEMBL2017291
synonym: GSK1210151A
approved: f
ligand name: I-BET151
type: SyntheticOrganicLigand

compound 9 [PMID: 23517011]
in ch i key: BLNKHZBHJDYSGF-UHFFFAOYSA-N
in ch i: InChI=1S/C20H19NO4/c1-12-19(13(2)25-21-12)16-9-17(11-18(10-16)24-14(3)22)20(23)15-7-5-4-6-8-15/h4-11,20,23H,1-3H3
iupac name: [3-(3,5-dimethyl-1,2-oxazol-4-yl)-5-[hydroxy(phenyl)methyl]phenyl] acetate
xref: CHEMBL2335153
approved: f
ligand name: compound 9 [PMID: 23517011]
type: SyntheticOrganicLigand

compound 4d [PMID: 21851057]
canonical SMILES: CCOc1cc(cc(c1)c1c(C)noc1C)C(O)C
isomeric SMILES: CCOc1cc(cc(c1)c1c(C)noc1C)C(O)C
in ch i key: AONNGYBECNOVTK-UHFFFAOYSA-N
in ch i: InChI=1S/C15H19NO3/c1-5-18-14-7-12(10(3)17)6-13(8-14)15-9(2)16-19-11(15)4/h6-8,10,17H,5H2,1-4H3
comment: This compound acts a an acetyl-lysine mimetic at the BD1 domains of BRD2 and BRD4 <Reference id=24610/>.
iupac name: 1-[3-(dimethyl-1,2-oxazol-4-yl)-5-ethoxyphenyl]ethan-1-ol
xref: CHEMBL1828986
approved: f
ligand name: compound 4d [PMID: 21851057]
type: SyntheticOrganicLigand

BzT-7
in ch i key: UYIVCPRWMLOCSB-UHFFFAOYSA-N
in ch i: InChI=1S/C17H14ClN5/c1-11-19-20-17-22(2)21-16(12-6-4-3-5-7-12)14-10-13(18)8-9-15(14)23(11)17/h3-10H,1-2H3
comment: BzT‑7 is a benzotriazepine which functions as an inhibitor of BET domain containing BRDs (BRDs 2, 3 and 4) <Reference id=24609/>.
iupac name: 8-chloro-1,4-dimethyl-6-phenyl-[1,2,4]triazolo[4,3-a][1,3,4]benzotriazepine
xref: CHEMBL1958337
approved: f
ligand name: BzT-7
type: SyntheticOrganicLigand

GW841819X
in ch i key: TUWDLUFFAHHNEF-UHFFFAOYSA-N
in ch i: InChI=1S/C25H21N5O2/c1-17-28-29-24-23(27-25(31)32-16-18-10-4-2-5-11-18)26-22(19-12-6-3-7-13-19)20-14-8-9-15-21(20)30(17)24/h2-15,23H,16H2,1H3,(H,27,31)
comment: GW841819X is a small molecule inhibitor of bromodomain and extraterminal (BET) subfamily of bromodomain containing proteins (BCPs; BRD2-4). The compound acts as a mimetic of acetylated lysine, competing for the acetylated histone binding site.
iupac name: phenylmethyl N-(1-methyl-6-phenyl-4H-[1,2,4]triazolo[4,3-a][1,4]benzodiazepin-4-yl)carbamate
xref: CHEMBL2153434
synonym: KB-75882
approved: f
ligand name: GW841819X
type: SyntheticOrganicLigand

metipranolol
canonical SMILES: OC(COc1cc(C)c(c(c1C)C)OC(=O)C)CNC(C)C
isomeric SMILES: OC(COc1cc(C)c(c(c1C)C)OC(=O)C)CNC(C)C
in ch i key: BQIPXWYNLPYNHW-UHFFFAOYSA-N
in ch i: InChI=1S/C17H27NO4/c1-10(2)18-8-15(20)9-21-16-7-11(3)17(22-14(6)19)13(5)12(16)4/h7,10,15,18,20H,8-9H2,1-6H3
comment: Metipranolol is a β-blocker. The drug's active metabolite is desacetylmetipranolol (CHEMBL1201363).
iupac name: 4-{2-hydroxy-3-[(propan-2-yl)amino]propoxy}-2,3,6-trimethylphenyl acetate
xref: CHEMBL1291
synonym: Metipranolol
synonym: Optipranolol®
synonym: VUAB-6453
synonym: BM-01004
synonym: VUAB6453
approved: t
ligand name: metipranolol
type: SyntheticOrganicLigand

CPI-203
in ch i key: QECMENZMDBOLDR-AWEZNQCLSA-N
in ch i: InChI=1S/C19H18ClN5OS/c1-9-10(2)27-19-16(9)17(12-4-6-13(20)7-5-12)22-14(8-15(21)26)18-24-23-11(3)25(18)19/h4-7,14H,8H2,1-3H3,(H2,21,26)/t14-/m0/s1
comment: CPI-203 is an amide analogue of <Ligand id=7511/>. CPI-203 has anti-proliferative activity in cancer cells <Reference id=32717/><Reference id=32718/>. Online information suggests that CPI-203 is the same chemical structure as the clinical oncology candidate with research code <Ligand id=9118/>, however we cannot confirm or refute this until the structure of TEN-101 is formally disclosed in a peer reviewed article.
synonym: CPI 203
synonym: CPI203
approved: f
ligand name: CPI-203
type: SyntheticOrganicLigand

MS417
in ch i key: GGRCIHACOIMRKY-HNNXBMFYSA-N
comment: MS417 is designed to block BRD4 binding to the acetylated NF-κB transcriptional complex <Reference id=24606/>.
approved: f
ligand name: MS417
type: SyntheticOrganicLigand

(+)-JQ1
in ch i key: DNVXATUJJDPFDM-KRWDZBQOSA-N
comment: JQ1 is a selective and potent inhibitor of BET family bromodomains <Reference id=24605/>. This is a compound from the Structural Genomics Consortium's (SGC) Epigenetics Probes Collection.
xref: CHEMBL1957266
approved: f
ligand name: (+)-JQ1
type: SyntheticOrganicLigand

BIC1
in ch i key: KDPSGIFCBZTBEZ-UHFFFAOYSA-N
in ch i: InChI=1S/C17H16N4S2/c1-20-14-8-4-5-9-15(14)21(17(20)22)10-11-23-16-18-12-6-2-3-7-13(12)19-16/h2-9H,10-11H2,1H3,(H,18,19)
comment: BIC1 (BRD2-interactive compound-1) inhibits the interaction between BRD2-BD1 and acetylated histone H4K12 without affecting the K12 acetylation level of histone H4 <Reference id=24604/>.
iupac name: 1-[2-(1H-benzimidazol-2-ylsulfanyl)ethyl]-3-methylbenzimidazole-2-thione
xref: CHEMBL1738777
approved: f
ligand name: BIC1
type: SyntheticOrganicLigand

MS436
isomeric SMILES: Nc1cc(O)c(cc1/N=N/c1ccc(cc1)S(=O)(=O)Nc1ccccn1)C
in ch i key: DZTGIRNXWSZBIM-QURGRASLSA-N
in ch i: InChI=1S/C18H17N5O3S/c1-12-10-16(15(19)11-17(12)24)22-21-13-5-7-14(8-6-13)27(25,26)23-18-4-2-3-9-20-18/h2-11,24H,19H2,1H3,(H,20,23)/b22-21+
comment: This compound binds to the Brd1 bromodomain of BRD4, with approximately 4-fold selectivity over the Brd2 bromodomain <Reference id=24603/>. PubChem CID 72672988 represents an alternative isomer of this molecule.
iupac name: 4-[2-(2-amino-5-methyl-4-oxocyclohexa-2,5-dien-1-ylidene)hydrazinyl]-N-pyridin-2-ylbenzenesulfonamide
xref: CHEMBL3086883
approved: f
ligand name: MS436
type: SyntheticOrganicLigand

MS7972
canonical SMILES: O=C1CCCc2c1n(C(=O)C)c1c2cccc1
isomeric SMILES: O=C1CCCc2c1n(C(=O)C)c1c2cccc1
in ch i key: MIGJEXKBUJPKJF-UHFFFAOYSA-N
in ch i: InChI=1S/C14H13NO2/c1-9(16)15-12-7-3-2-5-10(12)11-6-4-8-13(17)14(11)15/h2-3,5,7H,4,6,8H2,1H3
comment: This compound blocks K382-acetylated p53 association with the bromodomain of CBP <Reference id=24602/>.
iupac name: 9-acetyl-2,3,4,9-tetrahydro-1H-carbazol-1-one
xref: CHEMBL1236441
approved: f
ligand name: MS7972
type: SyntheticOrganicLigand

compound 1 [PMID: 15724976]
canonical SMILES: [NH3+]CCCNc1ccccc1[N+](=O)[O-]
isomeric SMILES: [NH3+]CCCNc1ccccc1[N+](=O)[O-]
in ch i key: GVGDDEYVTBKACE-UHFFFAOYSA-O
in ch i: InChI=1S/C9H13N3O2/c10-6-3-7-11-8-4-1-2-5-9(8)12(13)14/h1-2,4-5,11H,3,6-7,10H2/p+1
iupac name: 3-[(2-nitrophenyl)amino]propylazanium
xref: CHEMBL3220205
approved: f
ligand name: compound 1 [PMID: 15724976]
type: SyntheticOrganicLigand

ischemin
isomeric SMILES: NC1=CC(=O)C(=C/C/1=N/Nc1cc(c(cc1C)C)S(=O)(=O)O)C
in ch i key: WGEVKJVUKOELFY-QGOAFFKASA-N
in ch i: InChI=1S/C15H17N3O4S/c1-8-4-10(3)15(23(20,21)22)7-12(8)17-18-13-5-9(2)14(19)6-11(13)16/h4-7,17H,16H2,1-3H3,(H,20,21,22)/b18-13+
comment: Ischemin binds reversibly to the bromodomain of CREB-binding protein (CBP) and blocks CBP association with binding partners <Reference id=24600/>. This results in inhibition of transcription functions performed by p53. Note that ischemin is represented in different ways by different online resources and suppliers. We show the molecule with a specified E bond as this is the form used in the associated PDB solution NMR structure (shown on the CBP page). Whereas, the chemical description in <Reference id=24600/> leaves this bond unspecified (see PubChem CID 73010922).
iupac name: 5-[(2E)-2-(2-amino-5-methyl-4-oxocyclohexa-2,5-dien-1-ylidene)hydrazinyl]-2,4-dimethylbenzenesulfonic acid
synonym: MS120
approved: f
ligand name: ischemin
type: SyntheticOrganicLigand

scriptaid
canonical SMILES: ONC(=O)CCCCCn1c(=O)c2cccc3c2c(c1=O)ccc3
isomeric SMILES: ONC(=O)CCCCCn1c(=O)c2cccc3c2c(c1=O)ccc3
in ch i key: JTDYUFSDZATMKU-UHFFFAOYSA-N
in ch i: InChI=1S/C18H18N2O4/c21-15(19-24)10-2-1-3-11-20-17(22)13-8-4-6-12-7-5-9-14(16(12)13)18(20)23/h4-9,24H,1-3,10-11H2,(H,19,21)
comment: Scriptaid is a potent inhibitor of HDACs 1, 2, 3 and 6 <Reference id=24598/>, with lower potencies for other Class I and II HDACs <Reference id=23750/>.
iupac name: 6-(1,3-dioxobenzo[de]isoquinolin-2-yl)-N-hydroxyhexanamide
xref: CHEMBL96051
synonym: GNF-Pf-2024
synonym: scriptide
approved: f
ligand name: scriptaid
type: SyntheticOrganicLigand

nexturastat A
canonical SMILES: CCCCN(C(=O)Nc1ccccc1)Cc1ccc(cc1)C(=O)NO
isomeric SMILES: CCCCN(C(=O)Nc1ccccc1)Cc1ccc(cc1)C(=O)NO
in ch i key: JZWXMCPARMXZQV-UHFFFAOYSA-N
in ch i: InChI=1S/C19H23N3O3/c1-2-3-13-22(19(24)20-17-7-5-4-6-8-17)14-15-9-11-16(12-10-15)18(23)21-25/h4-12,25H,2-3,13-14H2,1H3,(H,20,24)(H,21,23)
comment: Nexturastat A is a potent and selective HDAC6 inhibitor <Reference id=24597/>.
iupac name: 4-{[butyl(phenylcarbamoyl)amino]methyl}-N-hydroxybenzamide
xref: CHEMBL2179618
synonym: S7473
approved: f
ligand name: nexturastat A
type: SyntheticOrganicLigand

resminostat
isomeric SMILES: ONC(=O)/C=C/c1ccn(c1)S(=O)(=O)c1ccc(cc1)CN(C)C
in ch i key: FECGNJPYVFEKOD-VMPITWQZSA-N
in ch i: InChI=1S/C16H19N3O4S/c1-18(2)11-13-3-6-15(7-4-13)24(22,23)19-10-9-14(12-19)5-8-16(20)17-21/h3-10,12,21H,11H2,1-2H3,(H,17,20)/b8-5+
comment: Resminostat is an HDAC inhibitor with selectivity for HDACs 1, 3 and 6, with significantly lower affinity for HDAC8 <Reference id=24592/>.
synonym: RAS2410
synonym: 4SC-201
synonym: BYK408740
approved: f
ligand name: resminostat
type: SyntheticOrganicLigand

RGFP109
canonical SMILES: O=C(Nc1ccccc1N)CCCCCNC(=O)c1ccc(cc1)C
isomeric SMILES: O=C(Nc1ccccc1N)CCCCCNC(=O)c1ccc(cc1)C
in ch i key: VOPDXHFYDJAYNS-UHFFFAOYSA-N
in ch i: InChI=1S/C20H25N3O2/c1-15-10-12-16(13-11-15)20(25)22-14-6-2-3-9-19(24)23-18-8-5-4-7-17(18)21/h4-5,7-8,10-13H,2-3,6,9,14,21H2,1H3,(H,22,25)(H,23,24)
comment: RGFP109 is a brain-penetrant HDAC inhibitor with selectivity for HDACs 1 and 3 <Reference id=24590/>.
iupac name: N-(2-aminophenyl)-6-[(4-methylphenyl)formamido]hexanamide
synonym: RG2833
synonym: RGFP-109
synonym: RG-2833
approved: f
ligand name: RGFP109
type: SyntheticOrganicLigand

RGFP966
isomeric SMILES: O=C(Nc1ccc(cc1N)F)/C=C/c1cnn(c1)C/C=C/c1ccccc1
in ch i key: BLVQHYHDYFTPDV-VCABWLAWSA-N
in ch i: InChI=1S/C21H19FN4O/c22-18-9-10-20(19(23)13-18)25-21(27)11-8-17-14-24-26(15-17)12-4-7-16-5-2-1-3-6-16/h1-11,13-15H,12,23H2,(H,25,27)/b7-4+,11-8+
comment: RGFP966 is a selective inhibitor of histone deacetylase 3 (HDAC3) <Reference id=24589/>. In rodent studies, RGFP966-induced inhibition of HDAC3 appears to enhance memory processes involved in extinction of drug-seeking behaviour <Reference id=24589/>.
iupac name: (2E)-N-(2-amino-4-fluorophenyl)-3-{1-[(2E)-3-phenylprop-2-en-1-yl]-1H-pyrazol-4-yl}prop-2-enamide
synonym: RGFP-966
approved: f
ligand name: RGFP966
type: SyntheticOrganicLigand

bufexamac
canonical SMILES: CCCCOc1ccc(cc1)CC(=O)NO
isomeric SMILES: CCCCOc1ccc(cc1)CC(=O)NO
in ch i key: MXJWRABVEGLYDG-UHFFFAOYSA-N
in ch i: InChI=1S/C12H17NO3/c1-2-3-8-16-11-6-4-10(5-7-11)9-12(14)13-15/h4-7,15H,2-3,8-9H2,1H3,(H,13,14)
comment: In addition to inhibition of COX enzymes, this drug has been discovered to inhibit class IIb HDACs (ie HDACs 6 and 10) <Reference id=24586/>.
iupac name: 2-(4-butoxyphenyl)-N-hydroxyacetamide
xref: CHEMBL94394
synonym: CP-1044-J3
synonym: Anderm
synonym: Paraderm®
synonym: Parfenac®
approved: t
ligand name: bufexamac
type: SyntheticOrganicLigand

dacinostat
isomeric SMILES: OCCN(Cc1ccc(cc1)/C=C/C(=O)NO)CCc1c[nH]c2c1cccc2
in ch i key: BWDQBBCUWLSASG-MDZDMXLPSA-N
in ch i: InChI=1S/C22H25N3O3/c26-14-13-25(12-11-19-15-23-21-4-2-1-3-20(19)21)16-18-7-5-17(6-8-18)9-10-22(27)24-28/h1-10,15,23,26,28H,11-14,16H2,(H,24,27)/b10-9+
comment: NVP-LAQ824 is a non-selective histone deacetylase (HDAC) inhibitor.
iupac name: (E)-N-hydroxy-3-[4-[[2-hydroxyethyl-[2-(1H-indol-3-yl)ethyl]amino]methyl]phenyl]prop-2-enamide
xref: CHEMBL356066
synonym: LAQ-824
synonym: NVP-LAQ824
approved: f
ligand name: dacinostat
type: SyntheticOrganicLigand

belinostat
canonical SMILES: ONC(=O)C=Cc1cccc(c1)S(=O)(=O)Nc1ccccc1
isomeric SMILES: ONC(=O)/C=C/c1cccc(c1)S(=O)(=O)Nc1ccccc1
in ch i key: NCNRHFGMJRPRSK-MDZDMXLPSA-N
in ch i: InChI=1S/C15H14N2O4S/c18-15(16-19)10-9-12-5-4-8-14(11-12)22(20,21)17-13-6-2-1-3-7-13/h1-11,17,19H,(H,16,18)/b10-9+
comment: Belinostat is a pan-histone deacetylase (HDAC) inhibitor <Reference id=24578/><Reference id=23750/>.
iupac name: (E)-N-hydroxy-3-[3-(phenylsulfamoyl)phenyl]prop-2-enamide
xref: CHEMBL408513
synonym: PXD-101
synonym: PXD101
synonym: Beleodaq®
approved: t
ligand name: belinostat
type: SyntheticOrganicLigand

apicidin
in ch i key: JWOGUUIOCYMBPV-GMFLJSBRSA-N
in ch i: InChI=1S/C34H49N5O6/c1-5-22(3)30-34(44)38-19-13-12-18-29(38)33(43)35-26(16-9-7-8-14-24(40)6-2)31(41)36-27(32(42)37-30)20-23-21-39(45-4)28-17-11-10-15-25(23)28/h10-11,15,17,21-22,26-27,29-30H,5-9,12-14,16,18-20H2,1-4H3,(H,35,43)(H,36,41)(H,37,42)/t22-,26-,27-,29+,30-/m0/s1
comment: Acipidin is a natural product fungal metabolite <Reference id=24583/>. It inhibits cancer cell proliferation <Reference id=24585/>, via histone deacetylase (HDAC) inhibition. The compound has broad-spectrum activity against apicomplexan parasites including Plasmodium species <Reference id=24583/>. The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
iupac name: (3S,6S,9S,12R)-3-[(2S)-butan-2-yl]-6-[(1-methoxyindol-3-yl)methyl]-9-(6-oxooctyl)-1,4,7,10-tetrazabicyclo[10.4.0]hexadecane-2,5,8,11-tetrone
xref: CHEMBL430060
synonym: OSI-2040
approved: f
ligand name: apicidin
type: NaturalProductLigand

CHF-5074
in ch i key: LIYLTQQDABRNRX-UHFFFAOYSA-N
in ch i: InChI=1S/C16H11Cl2FO2/c17-12-4-1-9(7-13(12)18)11-3-2-10(8-14(11)19)16(5-6-16)15(20)21/h1-4,7-8H,5-6H2,(H,20,21)
comment: CHF-5074 is a gamma-secretase modulator (GSM). These are small molecules (<600 Da) causing a product shift from Abeta42 toward shorter and less toxic Abeta fragments. Classical non-steroidal anti-inflammatory drugs (NSAIDs) constituted the first class of GSMs. This compound has advanced to phase I trials
iupac name: 1-[4-(3,4-dichlorophenyl)-3-fluorophenyl]cyclopropane-1-carboxylic acid
xref: CHEMBL196945
synonym: CHF5074
synonym: CHF 5074
approved: f
ligand name: CHF-5074
type: SyntheticOrganicLigand

compound 17 [PMID: 23888693]
in ch i key: XWNJYOGTDUJRND-UHFFFAOYSA-N
in ch i: InChI=1S/C18H26N2O3S2/c1-13-12-20(14(2)21)17-9-8-16(10-18(17)24-13)25(22,23)19-11-15-6-4-3-5-7-15/h3-7,13,16-19H,8-12H2,1-2H3
comment: This compound is an inhibitor of EP300 (p300 histone acetyltransferase) <Reference id=24582/>.
iupac name: 4-acetyl-N-benzyl-2-methyl-octahydro-2H-1,4-benzothiazine-7-sulfonamide
approved: f
ligand name: compound 17 [PMID: 23888693]
type: SyntheticOrganicLigand

SRTCX1003
in ch i key: BXSJTHFUADFIKS-UHFFFAOYSA-N
in ch i: InChI=1S/C23H23N5O3S/c29-22(27-23-24-8-15-32-23)17-5-3-6-18-20(17)26-21(25-18)16-4-1-2-7-19(16)31-14-11-28-9-12-30-13-10-28/h1-8,15H,9-14H2,(H,25,26)(H,24,27,29)
comment: SRTCX1003 activates sirtuin 1 (SIRT1), an NAD+-dependent protein deacetylase <Reference id=24581/>.
iupac name: 2-{2-[2-(morpholin-4-yl)ethoxy]phenyl}-N-(1,3-thiazol-2-yl)-1H-1,3-benzodiazole-4-carboxamide
approved: f
ligand name: SRTCX1003
type: SyntheticOrganicLigand

compound 9 [PMID: 23788254]
isomeric SMILES: ONC(=O)/C=C/c1ccc2c(c1)CCN2S(=O)(=O)c1ccc(cc1)OC
in ch i key: LMFNVOGHSBJWLX-YCRREMRBSA-N
in ch i: InChI=1S/C18H18N2O5S/c1-25-15-4-6-16(7-5-15)26(23,24)20-11-10-14-12-13(2-8-17(14)20)3-9-18(21)19-22/h2-9,12,22H,10-11H2,1H3,(H,19,21)/b9-3+
iupac name: (2E)-N-hydroxy-3-[1-(4-methoxybenzenesulfonyl)-2,3-dihydro-1H-indol-5-yl]prop-2-enamide
approved: f
ligand name: compound 9 [PMID: 23788254]
type: SyntheticOrganicLigand

diarylpropionitrile
canonical SMILES: N#CC(c1ccc(cc1)O)Cc1ccc(cc1)O
isomeric SMILES: N#CC(c1ccc(cc1)O)Cc1ccc(cc1)O
in ch i key: GHZHWDWADLAOIQ-UHFFFAOYSA-N
in ch i: InChI=1S/C15H13NO2/c16-10-13(12-3-7-15(18)8-4-12)9-11-1-5-14(17)6-2-11/h1-8,13,17-18H,9H2
comment: DPN is an estrogen receptor β selective agonist <Reference id=30093/>.
iupac name: 2,3-bis(4-hydroxyphenyl)propanenitrile
xref: CHEMBL334773
approved: f
ligand name: diarylpropionitrile
type: SyntheticOrganicLigand

TMP269
in ch i key: HORXBWNTEDOVKN-UHFFFAOYSA-N
comment: TMP269 is a histone deacetylase (HDAC) inhibitor with specificity for class IIa HDACs (HDACs 4, 5, 7 and 9) <Reference id=24579/>.
iupac name: N-{[4-(4-phenyl-1,3-thiazol-2-yl)oxan-4-yl]methyl}-3-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide
xref: CHEMBL3110004
synonym: TMFO1
synonym: compound 1 [PMID: 23524983]
synonym: TMP-269
synonym: TMP 269
approved: f
ligand name: TMP269
type: SyntheticOrganicLigand

givinostat
in ch i key: YALNUENQHAQXEA-UHFFFAOYSA-N
in ch i: InChI=1S/C24H27N3O4/c1-3-27(4-2)15-17-5-7-21-14-18(6-8-20(21)13-17)16-31-24(29)25-22-11-9-19(10-12-22)23(28)26-30/h5-14,30H,3-4,15-16H2,1-2H3,(H,25,29)(H,26,28)
comment: Givinostat is a pan-histone deacetylase (HDAC) inhibitor <Reference id=24578/>. The clinically used formulation contains the hydrochloride (PubChem CID 52914048).
iupac name: [6-(diethylaminomethyl)naphthalen-2-yl]methyl N-[4-(hydroxycarbamoyl)phenyl]carbamate
xref: CHEMBL1213492
synonym: ITF2357
synonym: ITF-2357
synonym: gavinostat
approved: f
ligand name: givinostat
type: SyntheticOrganicLigand

panobinostat
isomeric SMILES: ONC(=O)/C=C/c1ccc(cc1)CNCCc1c(C)[nH]c2c1cccc2
in ch i key: FPOHNWQLNRZRFC-ZHACJKMWSA-N
in ch i: InChI=1S/C21H23N3O2/c1-15-18(19-4-2-3-5-20(19)23-15)12-13-22-14-17-8-6-16(7-9-17)10-11-21(25)24-26/h2-11,22-23,26H,12-14H2,1H3,(H,24,25)/b11-10+
comment: Panobinostat is a non-selective histone deacetylase (HDAC) inhibitor <Reference id=24577/><Reference id=24578/>. The compound also has antimalarial activity. The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
iupac name: (E)-N-hydroxy-3-[4-[[2-(2-methyl-1H-indol-3-yl)ethylamino]methyl]phenyl]prop-2-enamide
xref: CHEMBL483254
synonym: Farydak®
synonym: LBH-589
synonym: LBH589
approved: t
ligand name: panobinostat
type: SyntheticOrganicLigand

MG149
canonical SMILES: CCCCCCCc1ccc(cc1)CCc1cccc(c1C(=O)O)O
isomeric SMILES: CCCCCCCc1ccc(cc1)CCc1cccc(c1C(=O)O)O
in ch i key: WBHQYBZRTAEHRR-UHFFFAOYSA-N
in ch i: InChI=1S/C22H28O3/c1-2-3-4-5-6-8-17-11-13-18(14-12-17)15-16-19-9-7-10-20(23)21(19)22(24)25/h7,9-14,23H,2-6,8,15-16H2,1H3,(H,24,25)
comment: MG148 is a derivative of <Ligand id=6999/>. This compound is an inhibitor of K(lysine) acetyltransferase 5 (KAT5 aka Tip60) and K(lysine) acetyltransferase 8 (KAT8 aka HMOF) <Reference id=24576/><Reference id=24575/>. However, a 2017 article by Dahlin et al. suggests that MG148 non-specifically perturbs biological assays, bringing in to question its HAT inhibitor activity <Reference id=33784/>.
iupac name: 2-[2-(4-heptylphenyl)ethyl]-6-hydroxybenzoic acid
xref: CHEMBL1215739
synonym: MG-149
synonym: MG 149
approved: f
ligand name: MG149
type: SyntheticOrganicLigand

palonosetron
canonical SMILES: O=C1N(CC2c3c1cccc3CCC2)C1CN2CCC1CC2
in ch i key: CPZBLNMUGSZIPR-NVXWUHKLSA-N
in ch i: InChI=1S/C19H24N2O/c22-19-16-6-2-4-14-3-1-5-15(18(14)16)11-21(19)17-12-20-9-7-13(17)8-10-20/h2,4,6,13,15,17H,1,3,5,7-12H2/t15-,17-/m1/s1
comment: Palonosetron is a 'serton' family drug, that is a serotonin 5-HT3 antagonist. Most setrons are antiemetics, apart from <Ligand id=2296/> and <Ligand id=2297/>, which are irritable bowel syndrome therapeutics. Setrons are the most widely prescribed antiemetic drugs used in the management of chemotherapy-induced nausea and vomiting (CINV).
iupac name: (3aS)-2-[(3S)-1-azabicyclo[2.2.2]octan-3-yl]-3a,4,5,6-tetrahydro-3H-benzo[de]isoquinolin-1-one
xref: CHEMBL1189679
synonym: RS-25259-197
synonym: aurothioglucose
synonym: Aloxi®
approved: t
ligand name: palonosetron
type: SyntheticOrganicLigand

azelaic acid
canonical SMILES: OC(=O)CCCCCCCC(=O)O
isomeric SMILES: OC(=O)CCCCCCCC(=O)O
in ch i key: BDJRBEYXGGNYIS-UHFFFAOYSA-N
in ch i: InChI=1S/C9H16O4/c10-8(11)6-4-2-1-3-5-7-9(12)13/h1-7H2,(H,10,11)(H,12,13)
comment: Azelaic acid is a saturated dicarboxylic acid, used clinically for its antibacterial and antiinflammatory actions, as well as for its ability to inhibit keratin and melanin production.
iupac name: Nonanedioic acid
xref: CHEMBL1238
synonym: ZK-62498
synonym: Skinoren
synonym: Finacea®
synonym: Azelex®
approved: t
ligand name: azelaic acid
type: SyntheticOrganicLigand

solifenacin
in ch i key: FBOUYBDGKBSUES-VXKWHMMOSA-N
in ch i: InChI=1S/C23H26N2O2/c26-23(27-21-16-24-13-10-18(21)11-14-24)25-15-12-17-6-4-5-9-20(17)22(25)19-7-2-1-3-8-19/h1-9,18,21-22H,10-16H2/t21-,22-/m0/s1
comment: The marketed formulation contains solifenacin succinate (PubChem CID 216457).
iupac name: [(8R)-1-azabicyclo[2.2.2]octan-8-yl] (1S)-1-phenyl-3,4-dihydro-1H-isoquinoline-2-carboxylate
xref: CHEMBL1734
synonym: YM-905
synonym: YM-67905
synonym: Vesicare®
approved: t
ligand name: solifenacin
type: SyntheticOrganicLigand

lumacaftor
in ch i key: UFSKUSARDNFIRC-UHFFFAOYSA-N
in ch i: InChI=1S/C24H18F2N2O5/c1-13-5-8-19(27-20(13)14-3-2-4-15(11-14)21(29)30)28-22(31)23(9-10-23)16-6-7-17-18(12-16)33-24(25,26)32-17/h2-8,11-12H,9-10H2,1H3,(H,29,30)(H,27,28,31)
comment: Lumacaftor is termed a cystic fibrosis transmembrane conductance regulator (CFTR) corrector, acting to reduce mis-folding of the defective F508del mutant CFTR protein, in comparison to <Ligand id=4342/> which is termed a CFTR potentiator drug. The F508del mutation is the most common cause of cystic fibrosis and accounts for approximately 60% of CF patients in Europe. Cryo-electron microscopy of CFTR-lumacaftor complexes provided insight into how the correctors operate at the molecular level, with the findings published in early 2022 by Fiedorczuk and Chen <Reference id=43351/>.
iupac name: 3-[6-[[1-(2,2-difluoro-1,3-benzodioxol-5-yl)cyclopropanecarbonyl]amino]-3-methylpyridin-2-yl]benzoic acid
xref: CHEMBL2103870
synonym: VX809
synonym: VRT-826809
synonym: VX-809
approved: t
ligand name: lumacaftor
type: SyntheticOrganicLigand

trospium
in ch i key: OYYDSUSKLWTMMQ-UHFFFAOYSA-N
in ch i: InChI=1S/C25H30NO3/c27-24(25(28,19-9-3-1-4-10-19)20-11-5-2-6-12-20)29-23-17-21-13-14-22(18-23)26(21)15-7-8-16-26/h1-6,9-12,21-23,28H,7-8,13-18H2/q+1
comment: The marketed product contains trospium chloride (PubChem CID 107979). Note that the INN record for trospium chloride represents a chiral molecule, the closest PubChem match being AC1NR4SW. Our representation and those contained in our links show the non-isomeric molecule.
iupac name: spiro[8-azoniabicyclo[3.2.1]octane-8,1'-azolidin-1-ium]-3-yl 2-hydroxy-2,2-di(phenyl)acetate
xref: CHEMBL1201344
synonym: IP631
synonym: IP-631
synonym: Sanctura®
synonym: Tropez OD
synonym: Trosec
synonym: Spasmex
synonym: Spasmolyt
synonym: Regurin®
synonym: Flotros®
approved: t
ligand name: trospium
type: SyntheticOrganicLigand

arformoterol
canonical SMILES: O=CNc1cc(ccc1O)C(CNC(Cc1ccc(cc1)OC)C)O
in ch i key: BPZSYCZIITTYBL-YJYMSZOUSA-N
in ch i: InChI=1S/C19H24N2O4/c1-13(9-14-3-6-16(25-2)7-4-14)20-11-19(24)15-5-8-18(23)17(10-15)21-12-22/h3-8,10,12-13,19-20,23-24H,9,11H2,1-2H3,(H,21,22)/t13-,19+/m1/s1
comment: Arformoterol is the active (R,R)-enantiomer of <Ligand id=3465/>. The marketed product contains arformoterol tartrate (PubChem CID 9827062).
iupac name: N-[2-hydroxy-5-[(1R)-1-hydroxy-2-[[(2R)-1-(4-methoxyphenyl)propan-2-yl]amino]ethyl]phenyl]formamide
xref: CHEMBL1363
synonym: Brovana®
synonym: YM-08316
approved: t
ligand name: arformoterol
type: SyntheticOrganicLigand

bendamustine
canonical SMILES: ClCCN(c1ccc2c(c1)nc(n2C)CCCC(=O)O)CCCl
isomeric SMILES: ClCCN(c1ccc2c(c1)nc(n2C)CCCC(=O)O)CCCl
in ch i key: YTKUWDBFDASYHO-UHFFFAOYSA-N
comment: The marketed formulation contains the hydrochloride salt (PubChem CID 77082).
iupac name: 4-[5-[bis(2-chloroethyl)amino]-1-methylbenzimidazol-2-yl]butanoic acid
xref: CHEMBL487253
synonym: Treakisym
synonym: Ribomustin
synonym: Treanda®
synonym: Levact®
synonym: SDX-105
approved: t
ligand name: bendamustine
type: SyntheticOrganicLigand

tapentadol
canonical SMILES: CCC(c1cccc(c1)O)C(CN(C)C)C
isomeric SMILES: CC[C@@H](c1cccc(c1)O)[C@H](CN(C)C)C
in ch i key: KWTWDQCKEHXFFR-SMDDNHRTSA-N
in ch i: InChI=1S/C14H23NO/c1-5-14(11(2)10-15(3)4)12-7-6-8-13(16)9-12/h6-9,11,14,16H,5,10H2,1-4H3/t11-,14+/m0/s1
comment: The marketed formulation contains tapentadol hydrochloride (PubChem CID 9838021).
iupac name: 3-[(2R,3R)-1-dimethylamino-2-methylpentan-3-yl]phenol
xref: CHEMBL1201776
synonym: BN-200
synonym: CG-5503
synonym: TAPAL
synonym: Nucynta®
synonym: Palexia®
approved: t
ligand name: tapentadol
type: SyntheticOrganicLigand

lorlatinib
in ch i key: IIXWYSCJSQVBQM-LLVKDONJSA-N
in ch i: InChI=1S/C21H19FN6O2/c1-11-15-7-13(22)4-5-14(15)21(29)27(2)10-16-19(17(8-23)28(3)26-16)12-6-18(30-11)20(24)25-9-12/h4-7,9,11H,10H2,1-3H3,(H2,24,25)/t11-/m1/s1
comment: Lorlatinib (PF-06463922) is a kinase inhibitor with action on ALK and ROS1 proto-oncogenes <Reference id=24549/><Reference id=27439/>. It is a reversible, ATP-competitive small molecule inhibitor. Lorlatinib is a third generation ALK inhibitor designed to have improved blood-brain barrier penetrance compared to older second generation ALK inhibitors such as the approved drugs <Ligand id=7397/>, <Ligand id=7739/>, and <Ligand id=7741/>, with the aim of better targeting metastatic NSCLC lesions in the brain. Advanced generation ALK inhibitors are those which target acquired ALK mutations resistant to the original first generation inhibitor <Ligand id=4903/>, which occur in virtually all AKL-rearranged NSCLC tumours within a year of starting crizotinib therapy. In fact, the cyano group of lortatinib is highly selective for the ALK mutation L1196M <Reference id=38409/>. Facchinetti et al. (2016) <Reference id=31500/> review the progress in ALK inhibitor development and discuss the importance of targeting therapies based on individual patient tumour profiles. Shaw et al.(2016) <Reference id=31501/> publish a case report of a patient with metastatic ALK-rearranged NSCLC whose tumours acquired sequential resistance to crizotinib, ceritinib and finally lorlatinib. However, the patient subsequently showed a resensitization to crizotinib. This patient was identified in a substudy of Phase 1/2 clinical trial NCT01970865, which is designed to compare lorlatinib against crizotinib in advanced NSCLC harbouring specific molecular alterations, such as the lorlatinib resistance-conferring mutation L1198F. The molecular biology behind this pheomenon is outlined in the Nature Reviews Cancer Research Highlight commentary by Shipman (2016) <Reference id=31503/>.
xref: CHEMBL3286830
synonym: Lorbrena®
synonym: PF06463922
synonym: PF-06463922
synonym: (10R)-7-amino-12-fluoro-2,10,16-trimethyl-15-oxo-10,15,16,17-tetrahydro-2H-4,8-methenopyrazolo[4,3-h][2,5,11]benzoxadiazacyclotetradecine-3-carbonitrile
synonym: Lorviqua®
approved: t
ligand name: lorlatinib
type: SyntheticOrganicLigand

fospropofol
canonical SMILES: CC(c1cccc(c1OCOP(=O)(O)O)C(C)C)C
isomeric SMILES: CC(c1cccc(c1OCOP(=O)(O)O)C(C)C)C
in ch i key: QVNNONOFASOXQV-UHFFFAOYSA-N
in ch i: InChI=1S/C13H21O5P/c1-9(2)11-6-5-7-12(10(3)4)13(11)17-8-18-19(14,15)16/h5-7,9-10H,8H2,1-4H3,(H2,14,15,16)
comment: Fospropofol is a prodrug which undergoes hepatic conversion to the active moeity, propofol.
iupac name: [2,6-di(propan-2-yl)phenoxy]methyl dihydrogen phosphate
xref: CHEMBL1201766
synonym: Aquavan
synonym: Lusedra®
approved: t
ligand name: fospropofol
type: SyntheticOrganicLigand

difluprednate
in ch i key: WYQPLTPSGFELIB-JTQPXKBDSA-N
in ch i: InChI=1S/C27H34F2O7/c1-5-6-23(34)36-26(22(33)14-35-15(2)30)10-8-17-18-12-20(28)19-11-16(31)7-9-24(19,3)27(18,29)21(32)13-25(17,26)4/h7,9,11,17-18,20-21,32H,5-6,8,10,12-14H2,1-4H3/t17-,18-,20-,21-,24-,25-,26-,27-/m0/s1
comment: Difluprednate is a corticosteroid with antiinflammatory action.
iupac name: [(6S,8S,9R,10S,11S,13S,14S,17R)-17-(2-acetyloxyacetyl)-6,9-difluoro-11-hydroxy-10,13-dimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl] butanoate
xref: CHEMBL1201749
synonym: W-6309
synonym: DFBA
synonym: Durezol®
approved: t
ligand name: difluprednate
type: NaturalProductLigand

fesoterodine
in ch i key: DCCSDBARQIPTGU-HSZRJFAPSA-N
in ch i: InChI=1S/C26H37NO3/c1-18(2)26(29)30-25-13-12-21(17-28)16-24(25)23(22-10-8-7-9-11-22)14-15-27(19(3)4)20(5)6/h7-13,16,18-20,23,28H,14-15,17H2,1-6H3/t23-/m1/s1
comment: The marketed formulation contains the fumarate compound (PubChem CID 9849808). Fesoterodine is an antimuscarinic prodrug, with the active metabolite being 5-hydroxymethyl tolterodine (5-HMT, PubChem CID 9819382).
iupac name: [2-[(1R)-3-(di(propan-2-yl)amino)-1-phenylpropyl]-4-(hydroxymethyl)phenyl] 2-methylpropanoate
xref: CHEMBL1201764
synonym: Toviaz®
synonym: SPM-907
synonym: SPM-8272
approved: t
ligand name: fesoterodine
type: SyntheticOrganicLigand

lacosamide
canonical SMILES: COCC(C(=O)NCc1ccccc1)NC(=O)C
isomeric SMILES: COC[C@H](C(=O)NCc1ccccc1)NC(=O)C
in ch i key: VPPJLAIAVCUEMN-GFCCVEGCSA-N
in ch i: InChI=1S/C13H18N2O3/c1-10(16)15-12(9-18-2)13(17)14-8-11-6-4-3-5-7-11/h3-7,12H,8-9H2,1-2H3,(H,14,17)(H,15,16)/t12-/m1/s1
comment: Lacosamide is a functionalized amino acid anticonvulsant drug <Reference id=31253/>.
iupac name: (2R)-2-acetamido-3-methoxy-N-(phenylmethyl)propanamide
xref: CHEMBL58323
synonym: erlosamide
synonym: harkeroside
synonym: SPM 927
synonym: ADD 234037
synonym: Vimpat®
approved: t
ligand name: lacosamide
type: SyntheticOrganicLigand

alvimopan
in ch i key: UPNUIXSCZBYVBB-JVFUWBCBSA-N
in ch i: InChI=1S/C25H32N2O4/c1-18-16-27(12-11-25(18,2)21-9-6-10-22(28)14-21)17-20(24(31)26-15-23(29)30)13-19-7-4-3-5-8-19/h3-10,14,18,20,28H,11-13,15-17H2,1-2H3,(H,26,31)(H,29,30)/t18-,20-,25+/m0/s1
comment: Alvimopan is a peripherally acting mu-opioid receptor antagonist , or PAMORA.
iupac name: 2-[[(2S)-2-[[(3R,4R)-4-(3-hydroxyphenyl)-3,4-dimethylpiperidin-1-yl]methyl]-3-phenylpropanoyl]amino]acetic acid
xref: CHEMBL270190
synonym: ADL 8-2698
synonym: Entereg®
approved: t
ligand name: alvimopan
type: SyntheticOrganicLigand

rufinamide
canonical SMILES: Fc1cccc(c1Cn1nnc(c1)C(=O)N)F
isomeric SMILES: Fc1cccc(c1Cn1nnc(c1)C(=O)N)F
in ch i key: POGQSBRIGCQNEG-UHFFFAOYSA-N
in ch i: InChI=1S/C10H8F2N4O/c11-7-2-1-3-8(12)6(7)4-16-5-9(10(13)17)14-15-16/h1-3,5H,4H2,(H2,13,17)
comment: Rufinamide is a triazole (a heterocyclic compound with molecular formula C2H3N3) derivative anticonvulsant drug.
iupac name: 1-[(2,6-difluorophenyl)methyl]triazole-4-carboxamide
xref: CHEMBL1201754
synonym: RUF-331
synonym: CGP-33101
synonym: Banzel®
synonym: Inovelon®
approved: t
ligand name: rufinamide
type: SyntheticOrganicLigand

ciclesonide
in ch i key: LUKZNWIVRBCLON-GXOBDPJESA-N
in ch i: InChI=1S/C32H44O7/c1-18(2)28(36)37-17-25(35)32-26(38-29(39-32)19-8-6-5-7-9-19)15-23-22-11-10-20-14-21(33)12-13-30(20,3)27(22)24(34)16-31(23,32)4/h12-14,18-19,22-24,26-27,29,34H,5-11,15-17H2,1-4H3/t22-,23-,24-,26+,27+,29+,30-,31-,32+/m0/s1
comment: Ciclesonide is a prodrug. The active metabolite is desisobutyrylciclesonide (PubChem CID 6918281). It is a clinically used inhalation corticosteroid/glucocorticoid drug.
xref: CHEMBL2040682
synonym: Zetonna
synonym: RPR-251526
synonym: Alvesco®
synonym: Omnaris®
approved: t
ligand name: ciclesonide
type: SyntheticOrganicLigand

clevidipine
in ch i key: KPBZROQVTHLCDU-UHFFFAOYSA-N
in ch i: InChI=1S/C21H23Cl2NO6/c1-5-7-15(25)29-10-30-21(27)17-12(3)24-11(2)16(20(26)28-4)18(17)13-8-6-9-14(22)19(13)23/h6,8-9,18,24H,5,7,10H2,1-4H3
comment: Clevidipine is a dihydropyridine class L-type calcium channel blocker, whic is highly selective for vascular smooth muscle over myocardial smooth muscle.
iupac name: O3-(butanoyloxymethyl) O5-methyl 4-(2,3-dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate
xref: CHEMBL1237132
synonym: Cleviprex®
approved: t
ligand name: clevidipine
type: SyntheticOrganicLigand

bepotastine
in ch i key: YWGDOWXRIALTES-NRFANRHFSA-N
in ch i: InChI=1S/C21H25ClN2O3/c22-17-8-6-16(7-9-17)21(19-4-1-2-12-23-19)27-18-10-14-24(15-11-18)13-3-5-20(25)26/h1-2,4,6-9,12,18,21H,3,5,10-11,13-15H2,(H,25,26)/t21-/m0/s1
comment: The marketed formulation contains the besilate salt (PubChem CID 164521).
iupac name: 4-[4-[(S)-(4-chlorophenyl)-pyridin-2-ylmethoxy]piperidin-1-yl]butanoic acid
xref: CHEMBL1201758
synonym: Bepreve
synonym: TAU-284
synonym: Talion®
approved: t
ligand name: bepotastine
type: SyntheticOrganicLigand

dronedarone
in ch i key: ZQTNQVWKHCQYLQ-UHFFFAOYSA-N
in ch i: InChI=1S/C31H44N2O5S/c1-5-8-12-29-30(27-23-25(32-39(4,35)36)15-18-28(27)38-29)31(34)24-13-16-26(17-14-24)37-22-11-21-33(19-9-6-2)20-10-7-3/h13-18,23,32H,5-12,19-22H2,1-4H3
comment: Dronedarone is a class III antiarrhythmic drug. It is a noniodinated analogue of <Ligand id=2566/>. The marketed formulation contains the hydrochloride salt (PubChem CID 219025).
iupac name: N-[2-butyl-3-[4-[3-(dibutylamino)propoxy]benzoyl]-1-benzofuran-5-yl]methanesulfonamide
xref: CHEMBL184412
synonym: SR-33598B
synonym: Multaq®
approved: t
ligand name: dronedarone
type: SyntheticOrganicLigand

lurasidone
in ch i key: PQXKDMSYBGKCJA-CVTJIBDQSA-N
in ch i: InChI=1S/C28H36N4O2S/c33-27-24-18-9-10-19(15-18)25(24)28(34)32(27)17-21-6-2-1-5-20(21)16-30-11-13-31(14-12-30)26-22-7-3-4-8-23(22)35-29-26/h3-4,7-8,18-21,24-25H,1-2,5-6,9-17H2/t18-,19+,20-,21-,24+,25-/m0/s1
comment: Lurasidone is an atypical antipsychotic with activity at serotonin family receptors that are involved in learning and memory. It is devoid of the anticholinergic effects which are common with most other antipsychotics.
xref: CHEMBL1237021
synonym: SM-13496
synonym: Latuda®
approved: t
ligand name: lurasidone
type: SyntheticOrganicLigand

ulipristal acetate
in ch i key: OOLLAFOLCSJHRE-ZHAKMVSLSA-N
in ch i: InChI=1S/C30H37NO4/c1-18(32)30(35-19(2)33)15-14-27-25-12-8-21-16-23(34)11-13-24(21)28(25)26(17-29(27,30)3)20-6-9-22(10-7-20)31(4)5/h6-7,9-10,16,25-27H,8,11-15,17H2,1-5H3/t25-,26+,27-,29-,30-/m0/s1
comment: Ulipristal acetate is a selective progesterone receptor modulator (SPRM) contained in certain emergency contraceptives.
iupac name: [(8S,11R,13S,14S,17R)-17-acetyl-11-(4-dimethylaminophenyl)-13-methyl-3-oxo-1,2,6,7,8,11,12,14,15,16-decahydrocyclopenta[a]phenanthren-17-yl] acetate
xref: CHEMBL260538
synonym: Ella
synonym: Esmya
synonym: CDB-2914
synonym: VA2914
synonym: EllaOne®
approved: t
ligand name: ulipristal acetate
type: NaturalProductLigand

glycopyrrolate
canonical SMILES: O=C(C(c1ccccc1)(C1CCCC1)O)OC1CC[N+](C1)(C)C
isomeric SMILES: O=C(C(c1ccccc1)(C1CCCC1)O)OC1CC[N+](C1)(C)C
in ch i key: ANGKOCUUWGHLCE-UHFFFAOYSA-N
in ch i: InChI=1S/C19H28NO3/c1-20(2)13-12-17(14-20)23-18(21)19(22,16-10-6-7-11-16)15-8-4-3-5-9-15/h3-5,8-9,16-17,22H,6-7,10-14H2,1-2H3/q+1
comment: Glycopyrrolate is the active moiety of the approved drug glycopyrronium bromide. It is an anticholinergic drug.
iupac name: (1,1-dimethylpyrrolidin-1-ium-3-yl) 2-cyclopentyl-2-hydroxy-2-phenylacetate
xref: CHEMBL1201335
synonym: Qbrexza&reg (glycopyrronium cloth)
synonym: Tovanor Breezhaler®
synonym: Seebri Neohaler®
synonym: AHR-504
synonym: Cuvposa
synonym: Tarodyn
synonym: Nodapton
synonym: Robinul®
approved: t
ligand name: glycopyrrolate
type: SyntheticOrganicLigand

carglumic acid
canonical SMILES: OC(=O)CCC(C(=O)O)NC(=O)N
isomeric SMILES: OC(=O)CC[C@@H](C(=O)O)NC(=O)N
in ch i key: LCQLHJZYVOQKHU-VKHMYHEASA-N
in ch i: InChI=1S/C6H10N2O5/c7-6(13)8-3(5(11)12)1-2-4(9)10/h3H,1-2H2,(H,9,10)(H,11,12)(H3,7,8,13)/t3-/m0/s1
comment: Carglumic acid is an orphan drug.
iupac name: (2S)-2-(carbamoylamino)pentanedioic acid
xref: CHEMBL1201780
synonym: OE-312
synonym: Carbaglu®
synonym: N-carbamylglutamate
approved: t
ligand name: carglumic acid
type: SyntheticOrganicLigand

dutasteride
in ch i key: JWJOTENAMICLJG-QWBYCMEYSA-N
in ch i: InChI=1S/C27H30F6N2O2/c1-24-11-9-17-15(4-8-21-25(17,2)12-10-22(36)35-21)16(24)6-7-19(24)23(37)34-20-13-14(26(28,29)30)3-5-18(20)27(31,32)33/h3,5,10,12-13,15-17,19,21H,4,6-9,11H2,1-2H3,(H,34,37)(H,35,36)/t15-,16-,17-,19+,21+,24-,25+/m0/s1
comment: Dutasteride is a 5α-reductase inhibitor, which inhibits conversion of <Ligand id=2858/> to <Ligand id=2856/> (DHT). There are three 5α-reductase isozymes: SRD5A1, SRD5A2 and SRD5A3, all of which are inhibited by dutasteride <Reference id=31251/><Reference id=31252/>.
iupac name: (1S,3aS,3bS,5aR,9aR,9bS,11aS)-N-[2,5-bis(trifluoromethyl)phenyl]-9a,11a-dimethyl-7-oxo-1,2,3,3a,3b,4,5,5a,6,9b,10,11-dodecahydroindeno[5,4-f]quinoline-1-carboxamide
xref: CHEMBL1200969
synonym: GI-198745
synonym: GG-745
synonym: Avodart®
approved: t
ligand name: dutasteride
type: NaturalProductLigand

deferiprone
canonical SMILES: Cn1ccc(=O)c(c1C)O
isomeric SMILES: Cn1ccc(=O)c(c1C)O
in ch i key: TZXKOCQBRNJULO-UHFFFAOYSA-N
in ch i: InChI=1S/C7H9NO2/c1-5-7(10)6(9)3-4-8(5)2/h3-4,10H,1-2H3
comment: Deferiprone is an iron-chelating drug.
iupac name: 3-hydroxy-1,2-dimethylpyridin-4-one
xref: CHEMBL70927
synonym: CP20
synonym: APO-66
synonym: Ferriprox®
approved: t
ligand name: deferiprone
type: SyntheticOrganicLigand

phentermine
canonical SMILES: CC(Cc1ccccc1)(N)C
isomeric SMILES: CC(Cc1ccccc1)(N)C
in ch i key: DHHVAGZRUROJKS-UHFFFAOYSA-N
in ch i: InChI=1S/C10H15N/c1-10(2,11)8-9-6-4-3-5-7-9/h3-7H,8,11H2,1-2H3
comment: Phentermine is a stimulant similar to amphetamines.
iupac name: 2-methyl-1-phenylpropan-2-amine
xref: CHEMBL1574
synonym: TORA
synonym: WILPO
synonym: Fastin
synonym: Oby-Trim
synonym: Ona-Mast
synonym: Suprenza
synonym: Obestin-30
synonym: Phentermine Resin 30
synonym: Adipex-P®
synonym: phentermine hydrochloride
synonym: Ionamin®
approved: t
ligand name: phentermine
type: SyntheticOrganicLigand

indacaterol
in ch i key: QZZUEBNBZAPZLX-QFIPXVFZSA-N
in ch i: InChI=1S/C24H28N2O3/c1-3-14-9-16-11-18(12-17(16)10-15(14)4-2)25-13-22(28)19-5-7-21(27)24-20(19)6-8-23(29)26-24/h5-10,18,22,25,27-28H,3-4,11-13H2,1-2H3,(H,26,29)/t22-/m0/s1
comment: Only the R-enantiomer, as the maleate salt (PubChem CID 9827599) is contained in the medicinal product.
iupac name: 5-[(1R)-2-[(5,6-diethyl-2,3-dihydro-1H-inden-2-yl)amino]-1-hydroxyethyl]-8-hydroxy-1H-quinolin-2-one
xref: CHEMBL1095777
synonym: QAB149
synonym: QAB-149
synonym: Onbrez®
synonym: Arcapta Neohaler®
approved: t
ligand name: indacaterol
type: SyntheticOrganicLigand

omacetaxine mepesuccinate
in ch i key: HYFHYPWGAURHIV-JFIAXGOJSA-N
in ch i: InChI=1S/C29H39NO9/c1-27(2,33)8-5-10-29(34,16-23(31)36-4)26(32)39-25-22(35-3)15-28-9-6-11-30(28)12-7-18-13-20-21(38-17-37-20)14-19(18)24(25)28/h13-15,24-25,33-34H,5-12,16-17H2,1-4H3/t24-,25-,28+,29-/m1/s1
comment: Omacetaxine mepesuccinate is a semi-synthetic derivative of the alkaloid cephalotaxine from Cephalotaxus harringtonia. Note that this compound is represented on Drugbank with slightly different stereochemistry by the entry DB04865.
xref: CHEMBL46286
synonym: Myelostat®
synonym: homoharringtonine
synonym: HHT
synonym: CGX-635
synonym: Synribo®
approved: t
ligand name: omacetaxine mepesuccinate
type: NaturalProductLigand

tafluprost acid
isomeric SMILES: OC(=O)CCC/C=C/C[C@H]1[C@@H](O)C[C@H]([C@@H]1/C=C/C(COc1ccccc1)(F)F)O
in ch i key: KIQXRQVVYTYYAZ-VKVYFNERSA-N
in ch i: InChI=1S/C22H28F2O5/c23-22(24,15-29-16-8-4-3-5-9-16)13-12-18-17(19(25)14-20(18)26)10-6-1-2-7-11-21(27)28/h1,3-6,8-9,12-13,17-20,25-26H,2,7,10-11,14-15H2,(H,27,28)/b6-1-,13-12+/t17-,18-,19+,20-/m1/s1
comment: This is the active metabolite of <Ligand id=7451/> <Reference id=24510/>.
iupac name: (Z)-7-[(1R,2R,3R,5S)-2-[(E)-3,3-difluoro-4-(phenoxy)but-1-enyl]-3,5-dihydroxycyclopentyl]hept-5-enoic acid
synonym: AFP-172
approved: f
ligand name: tafluprost acid
type: SyntheticOrganicLigand

tafluprost
isomeric SMILES: CC(OC(=O)CCC/C=C/C[C@H]1[C@@H](O)C[C@H]([C@@H]1/C=C/C(COc1ccccc1)(F)F)O)C
in ch i key: WSNODXPBBALQOF-VEJSHDCNSA-N
in ch i: InChI=1S/C25H34F2O5/c1-18(2)32-24(30)13-9-4-3-8-12-20-21(23(29)16-22(20)28)14-15-25(26,27)17-31-19-10-6-5-7-11-19/h3,5-8,10-11,14-15,18,20-23,28-29H,4,9,12-13,16-17H2,1-2H3/b8-3-,15-14+/t20-,21-,22+,23-/m1/s1
comment: Tafluprost is a prostaglandin analogue.
iupac name: propan-2-yl (Z)-7-[(1R,2R,3R,5S)-2-[(E)-3,3-difluoro-4-(phenoxy)but-1-enyl]-3,5-dihydroxycyclopentyl]hept-5-enoate
xref: CHEMBL1963683
synonym: AFP-168
synonym: MK-2452
synonym: Taflotan®
synonym: Zioptan®
approved: t
ligand name: tafluprost
type: SyntheticOrganicLigand

aclidinium
canonical SMILES: O=C(C(c1cccs1)(c1cccs1)O)OC1C[N+]2(CCCOc3ccccc3)CCC1CC2
isomeric SMILES: O=C(C(c1cccs1)(c1cccs1)O)O[C@H]1C[N+]2(CCCOc3ccccc3)CCC1CC2
in ch i key: ASMXXROZKSBQIH-VITNCHFBSA-N
in ch i: InChI=1S/C26H30NO4S2/c28-25(26(29,23-9-4-17-32-23)24-10-5-18-33-24)31-22-19-27(14-11-20(22)12-15-27)13-6-16-30-21-7-2-1-3-8-21/h1-5,7-10,17-18,20,22,29H,6,11-16,19H2/q+1/t20?,22-,27?/m0/s1
comment: Note that the approved drug is the bromide salt (PubChem CID 11434515).
iupac name: [(8R)-1-[3-(phenoxy)propyl]-1-azoniabicyclo[2.2.2]octan-8-yl] 2-hydroxy-2,2-di(thiophen-2-yl)acetate
xref: CHEMBL1194325
synonym: LAS W-330
synonym: LAS-34273
synonym: Bretaris Genuair
synonym: Eklira Genuair
synonym: Tudorza Pressair®
approved: t
ligand name: aclidinium
type: SyntheticOrganicLigand

avanafil
in ch i key: WEAJZXNPAWBCOA-INIZCTEOSA-N
in ch i: InChI=1S/C23H26ClN7O3/c1-34-19-6-5-15(10-18(19)24)11-27-21-17(22(33)28-13-20-25-7-3-8-26-20)12-29-23(30-21)31-9-2-4-16(31)14-32/h3,5-8,10,12,16,32H,2,4,9,11,13-14H2,1H3,(H,28,33)(H,27,29,30)/t16-/m0/s1
comment: Avanafil is a phosphodiesterase type 5 inhibitor.
iupac name: 4-[(3-chloro-4-methoxyphenyl)methylamino]-2-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]-N-(pyrimidin-2-ylmethyl)pyrimidine-5-carboxamide
xref: CHEMBL1963681
synonym: TA-1790
synonym: Stendra®
synonym: Spedra®
approved: t
ligand name: avanafil
type: SyntheticOrganicLigand

mirabegron
in ch i key: PBAPPPCECJKMCM-IBGZPJMESA-N
in ch i: InChI=1S/C21H24N4O2S/c22-21-25-18(14-28-21)12-20(27)24-17-8-6-15(7-9-17)10-11-23-13-19(26)16-4-2-1-3-5-16/h1-9,14,19,23,26H,10-13H2,(H2,22,25)(H,24,27)/t19-/m0/s1
comment: Mirabegron is a β3-adrenoceptor agonist muscle relaxant. It has been reported to exert effects on cellular metabolism in adipocytes. This latter action is β3-adrenoceptor-dependent, and improves glucose handling in vivo <Reference id=40226/>.
xref: CHEMBL2095212
synonym: YM-178
synonym: Betanis
synonym: Betmiga®
synonym: Myrbetriq®
approved: t
ligand name: mirabegron
type: SyntheticOrganicLigand

linsitinib
in ch i key: PKCDDUHJAFVJJB-VLZXCDOPSA-N
in ch i: InChI=1S/C26H23N5O/c1-26(32)14-19(15-26)25-30-22(23-24(27)28-11-12-31(23)25)18-8-7-17-9-10-20(29-21(17)13-18)16-5-3-2-4-6-16/h2-13,19,32H,14-15H2,1H3,(H2,27,28)/t19-,26+
comment: Note that the chemical structure in the PubChem record is for the non-stereo molecule. The INN record specifies stereochemistry as shown in our chemical structure.
iupac name: 3-[8-amino-1-(2-phenylquinolin-7-yl)imidazo[1,5-a]pyrazin-3-yl]-1-methylcyclobutan-1-ol
xref: CHEMBL1091644
synonym: OSI906
synonym: OSI 906
synonym: OSI-906
synonym: ASP-7487
approved: f
ligand name: linsitinib
type: SyntheticOrganicLigand

ingenol mebutate
in ch i key: VDJHFHXMUKFKET-WDUFCVPESA-N
in ch i: InChI=1S/C25H34O6/c1-7-12(2)22(29)31-21-13(3)10-24-14(4)8-17-18(23(17,5)6)16(20(24)28)9-15(11-26)19(27)25(21,24)30/h7,9-10,14,16-19,21,26-27,30H,8,11H2,1-6H3/b12-7-/t14-,16+,17-,18+,19-,21+,24+,25+/m1/s1
comment: Ingenol mebutate is extracted from the plant Euphorbia peplus.
xref: CHEMBL1863513
synonym: PEP-005
synonym: Picato®
approved: t
ligand name: ingenol mebutate
type: NaturalProductLigand

JNJ-16567083
in ch i key: VEURHZYLLRSEGL-RHNCMZPLSA-N
in ch i: InChI=1S/C20H25NO2/c1-4-14-11-17-12-16(7-10-19(17)21-13(14)2)20(22)15-5-8-18(23-3)9-6-15/h7,10-12,15,18H,4-6,8-9H2,1-3H3/t15-,18+
comment: This compound is represented on PubChem as the non-isomeric structure CID 9948645.
iupac name: (3-ethyl-2-methylquinolin-6-yl)-(4-methoxycyclohexyl)methanone
xref: CHEMBL188906
approved: f
ligand name: JNJ-16567083
type: SyntheticOrganicLigand

icosapent
canonical SMILES: CCC=CCC=CCC=CCC=CCC=CCCCC(=O)OCC
isomeric SMILES: CC/C=C/C/C=C/C/C=C/C/C=C/C/C=C/CCCC(=O)OCC
in ch i key: SSQPWTVBQMWLSZ-AAQCHOMXSA-N
comment: Icosapent is a synthetic ethyl ester derivative of the omega-3 fatty acid eicosapentaenoic acid (EPA). It is de-esterified during absorption to active EPA that is absorbed in the small intestine.
iupac name: ethyl (5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoate
xref: CHEMBL2095209
synonym: AMR-101
synonym: icosapentate
synonym: Vascepa®
synonym: Vazkepa®
synonym: icosapent ethyl
approved: t
ligand name: icosapent
type: SyntheticOrganicLigand

mercaptamine
canonical SMILES: NCCS
isomeric SMILES: NCCS
in ch i key: UFULAYFCSOUIOV-UHFFFAOYSA-N
in ch i: InChI=1S/C2H7NS/c3-1-2-4/h4H,1-3H2
comment: Mercaptamine is the simplest stable aminothiol, and a degradation product of the amino acid cysteine.
iupac name: 2-Aminoethanethiol
xref: CHEMBL602
synonym: Cystagon®
synonym: Procysbi
synonym: CI-9148
synonym: L-1573
synonym: Cystaran®
synonym: cysteamine hydrochloride
approved: t
ligand name: mercaptamine
type: SyntheticOrganicLigand

lomitapide
in ch i key: MBBCVAKAJPKAKM-UHFFFAOYSA-N
in ch i: InChI=1S/C39H37F6N3O2/c40-38(41,42)25-46-36(50)37(33-13-5-3-10-30(33)31-11-4-6-14-34(31)37)21-7-8-22-48-23-19-28(20-24-48)47-35(49)32-12-2-1-9-29(32)26-15-17-27(18-16-26)39(43,44)45/h1-6,9-18,28H,7-8,19-25H2,(H,46,50)(H,47,49)
comment: Lomitapide is a lipid-lowering agent for the treatment of familial hypercholesterolemia.
xref: CHEMBL354541
synonym: Lojuxta®
synonym: AEGR-733
synonym: BMS-201038
synonym: Juxtapid®
approved: t
ligand name: lomitapide
type: SyntheticOrganicLigand

methacholine
canonical SMILES: CC(C[N+](C)(C)C)OC(=O)C
isomeric SMILES: CC(C[N+](C)(C)C)OC(=O)C
in ch i key: NZWOPGCLSHLLPA-UHFFFAOYSA-N
in ch i: InChI=1S/C8H18NO2/c1-7(11-8(2)10)6-9(3,4)5/h7H,6H2,1-5H3/q+1
comment: The approved drug is methacholine chloride PubChem CID 6114. Note that the approved drug is a racemic mixture of enantiomers. We show the non-chiral molecule to represent this mixture.
iupac name: 2-acetyloxypropyl-trimethylazanium
xref: CHEMBL978
synonym: Provocholine®
synonym: methacholine bromide
approved: t
ligand name: methacholine
type: SyntheticOrganicLigand

milnacipran
canonical SMILES: NCC1CC1(c1ccccc1)C(=O)N(CC)CC
isomeric SMILES: NCC1CC1(c1ccccc1)C(=O)N(CC)CC
in ch i key: GJJFMKBJSRMPLA-UHFFFAOYSA-N
in ch i: InChI=1S/C15H22N2O/c1-3-17(4-2)14(18)15(10-13(15)11-16)12-8-6-5-7-9-12/h5-9,13H,3-4,10-11,16H2,1-2H3
comment: Milnacipran is approved as a racemic mixture of enantiomers. We show the non-isomeric structure to represent the mixture.
iupac name: 2-(aminomethyl)-N,N-diethyl-1-phenylcyclopropane-1-carboxamide
xref: CHEMBL259209
synonym: Ixel
synonym: Dalcipran
synonym: Toledomin
synonym: Savella®
synonym: Ixel®
approved: t
ligand name: milnacipran
type: SyntheticOrganicLigand

levomilnacipran
canonical SMILES: NCC1CC1(c1ccccc1)C(=O)N(CC)CC
isomeric SMILES: NC[C@@H]1C[C@]1(c1ccccc1)C(=O)N(CC)CC
in ch i key: GJJFMKBJSRMPLA-DZGCQCFKSA-N
in ch i: InChI=1S/C15H22N2O/c1-3-17(4-2)14(18)15(10-13(15)11-16)12-8-6-5-7-9-12/h5-9,13H,3-4,10-11,16H2,1-2H3/t13-,15+/m0/s1
comment: Levomilnacipran is the active enantiomer of <Ligand id=7436/>. <Reference id=24485/>. It is a selective serotonin and norepinephrine reuptake inhibitor antidepressant (SNRI).
iupac name: (1S,2R)-2-(aminomethyl)-N,N-diethyl-1-phenylcyclopropane-1-carboxamide
xref: CHEMBL99946
synonym: F-2695
synonym: Fetzima®
approved: t
ligand name: levomilnacipran
type: SyntheticOrganicLigand

budesonide
in ch i key: VOVIALXJUBGFJZ-KWVAZRHASA-N
in ch i: InChI=1S/C25H34O6/c1-4-5-21-30-20-11-17-16-7-6-14-10-15(27)8-9-23(14,2)22(16)18(28)12-24(17,3)25(20,31-21)19(29)13-26/h8-10,16-18,20-22,26,28H,4-7,11-13H2,1-3H3/t16-,17-,18-,20+,21?,22+,23-,24-,25+/m0/s1
comment: Budesonide is a glucocorticoid steroid. The INN document specifies that the approved drug consists of a racemic mixture of two epimers, based on the stereocentre of the carbon where the butyl chain meets the rest of the molecule. Our structure does not specify strereochemistry at this point and represents the mixture. The two epimers are represented by CID 40000 and CID 63006. COVID-19: Results from a Phase 2 clinical trial have shown that a short duration administration of budesonide in the early phase of SARS-CoV-2 infection reduces both the likelihood of needing urgent medical care and time to recovery <Reference id=41964/>.
xref: CHEMBL1370
synonym: Jorveza®
synonym: S-1320
synonym: Rhinocort
synonym: Entocort Ec
synonym: Pulmicort®
synonym: Uceris®
synonym: Budeson
synonym: Rhinosol
synonym: Entocort®
synonym: Eohilia® (budesonide oral suspension)
approved: t
ligand name: budesonide
type: NaturalProductLigand

birinapant
in ch i key: PKWRMUKBEYJEIX-DXXQBUJASA-N
in ch i: InChI=1S/C42H56F2N8O6/c1-7-33(49-39(55)21(3)45-5)41(57)51-19-27(53)15-25(51)17-31-29-11-9-23(43)13-35(29)47-37(31)38-32(30-12-10-24(44)14-36(30)48-38)18-26-16-28(54)20-52(26)42(58)34(8-2)50-40(56)22(4)46-6/h9-14,21-22,25-28,33-34,45-48,53-54H,7-8,15-20H2,1-6H3,(H,49,55)(H,50,56)/t21-,22-,25-,26-,27-,28-,33-,34-/m0/s1
comment: Birinapant is an experimental anti-cancer compound.
xref: CHEMBL3039522
synonym: TL 32711
synonym: TL-32711
synonym: TL32711
approved: f
ligand name: birinapant
type: SyntheticOrganicLigand

zopiclone
in ch i key: GBBSUAFBMRNDJC-UHFFFAOYSA-N
in ch i: InChI=1S/C17H17ClN6O3/c1-22-6-8-23(9-7-22)17(26)27-16-14-13(19-4-5-20-14)15(25)24(16)12-3-2-11(18)10-21-12/h2-5,10,16H,6-9H2,1H3
comment: Zopiclone is a racemic mixture of the R and S chemical stereoisomers (PubChem CID 941731 and <Ligand id=7429/> respectively). Eszopiclone is an approved drug in its own right.
iupac name: [6-(5-chloropyridin-2-yl)-5-oxo-7H-pyrrolo[3,4-b]pyrazin-7-yl] 4-methylpiperazine-1-carboxylate
xref: CHEMBL135400
synonym: RP-27267
synonym: Imovane
synonym: Zimovane®
approved: t
ligand name: zopiclone
type: SyntheticOrganicLigand

hexestrol
canonical SMILES: CCC(C(c1ccc(cc1)O)CC)c1ccc(cc1)O
isomeric SMILES: CCC(C(c1ccc(cc1)O)CC)c1ccc(cc1)O
in ch i key: PBBGSZCBWVPOOL-UHFFFAOYSA-N
in ch i: InChI=1S/C18H22O2/c1-3-17(13-5-9-15(19)10-6-13)18(4-2)14-7-11-16(20)12-8-14/h5-12,17-20H,3-4H2,1-2H3
iupac name: 4-[4-(4-hydroxyphenyl)hexan-3-yl]phenol
xref: CHEMBL6615
approved: f
ligand name: hexestrol
type: SyntheticOrganicLigand

moclobemide
canonical SMILES: O=C(c1ccc(cc1)Cl)NCCN1CCOCC1
isomeric SMILES: O=C(c1ccc(cc1)Cl)NCCN1CCOCC1
in ch i key: YHXISWVBGDMDLQ-UHFFFAOYSA-N
in ch i: InChI=1S/C13H17ClN2O2/c14-12-3-1-11(2-4-12)13(17)15-5-6-16-7-9-18-10-8-16/h1-4H,5-10H2,(H,15,17)
comment: Moclobemide is a reversible inhibitor of monoamine oxidase A (RIMA) <Reference id=31250/>. It is an antidepressant and anxiolytic (antianxiety) drug.
iupac name: 4-chloro-N-(2-morpholin-4-ylethyl)benzamide
xref: CHEMBL86304
synonym: Aurorix
synonym: Amira
synonym: Clobemix
synonym: Depnil
synonym: Clorix
synonym: GNF-Pf-695
synonym: Manerix®
approved: t
ligand name: moclobemide
type: SyntheticOrganicLigand

vilazodone
in ch i key: SGEGOXDYSFKCPT-UHFFFAOYSA-N
in ch i: InChI=1S/C26H27N5O2/c27-16-18-4-6-23-22(13-18)19(17-29-23)3-1-2-8-30-9-11-31(12-10-30)21-5-7-24-20(14-21)15-25(33-24)26(28)32/h4-7,13-15,17,29H,1-3,8-12H2,(H2,28,32)
comment: Note that the USAN (United States Adopted Name) refers to the hydrochloride salt which has PubChem CID 6918313.
iupac name: 5-[4-[4-(5-cyano-1H-indol-3-yl)butyl]piperazin-1-yl]-1-benzofuran-2-carboxamide
xref: CHEMBL439849
synonym: EMD-68-843
synonym: EMD-515259
synonym: SB-659746-A
synonym: Viibryd®
approved: t
ligand name: vilazodone
type: SyntheticOrganicLigand

lenvatinib
in ch i key: WOSKHXYHFSIKNG-UHFFFAOYSA-N
in ch i: InChI=1S/C21H19ClN4O4/c1-29-19-10-17-13(9-14(19)20(23)27)18(6-7-24-17)30-12-4-5-16(15(22)8-12)26-21(28)25-11-2-3-11/h4-11H,2-3H2,1H3,(H2,23,27)(H2,25,26,28)
comment: Lenvatinib is a potent inhibitor of VEGFR-2 (KDR) and VEGFR-3 (FLT4) <Reference id=23537/>.
iupac name: 4-[3-chloro-4-(cyclopropylcarbamoylamino)phenoxy]-7-methoxyquinoline-6-carboxamide
xref: CHEMBL1289601
synonym: Kisplyx®
synonym: Lenvima®
synonym: E 7080
synonym: ER-203492-00
approved: t
ligand name: lenvatinib
type: SyntheticOrganicLigand

perifosine
canonical SMILES: CCCCCCCCCCCCCCCCCCOP(=O)(OC1CC[N+](CC1)(C)C)[O-]
isomeric SMILES: CCCCCCCCCCCCCCCCCCOP(=O)(OC1CC[N+](CC1)(C)C)[O-]
in ch i key: SZFPYBIJACMNJV-UHFFFAOYSA-N
iupac name: (1,1-dimethylpiperidin-1-ium-4-yl) octadecyl phosphate
xref: CHEMBL372764
synonym: KRX-0401
synonym: NSC 639966
synonym: D 21266
approved: f
ligand name: perifosine
type: SyntheticOrganicLigand

tolrestat
in ch i key: LUBHDINQXIHVLS-UHFFFAOYSA-N
in ch i: InChI=1S/C16H14F3NO3S/c1-20(8-13(21)22)15(24)11-5-3-4-10-9(11)6-7-12(23-2)14(10)16(17,18)19/h3-7H,8H2,1-2H3,(H,21,22)
comment: Tolrestat is an aldose reductase inhibitor <Reference id=24447/> that failed Phase 3 clinical trial in the US and never made it to the clinic. The manufacturer withdrew the drug from other markets due to toxicity concerns.
iupac name: 2-[[6-methoxy-5-(trifluoromethyl)naphthalene-1-carbothioyl]-methylamino]acetic acid
xref: CHEMBL436
synonym: AY-27773
synonym: AY-27,773
synonym: Alredase®
approved: t
ligand name: tolrestat
type: SyntheticOrganicLigand

dacomitinib
isomeric SMILES: COc1cc2ncnc(c2cc1NC(=O)/C=C/CN1CCCCC1)Nc1ccc(c(c1)Cl)F
in ch i key: LVXJQMNHJWSHET-AATRIKPKSA-N
comment: Dacomitinib is a second-generation, irreversible pan inhibitor of HER tyrosine kinases (EGFR, and ERBBs) that was developed by Pfizer. Results from the ARCHER 1050 Phase 3 randomised, open-label trial (NCT01774721) that directly compared dacomitinib against <Ligand id=4941/>, as first-line treatment for patients with EGFR-mutation +ve non-small-cell lung cancer (NSCLC), reported that dacomitinib significantly increased progression-free survival and overall survival compared to gefitinib <Reference id=35196/>. Dacomitinib's use may be limited in NSCLC patients with brain metastases, as these patients were excluded from the trial because dacomitinib's ability to cross the blood-brain-barrier has not been fully confirmed. This is unlike <Ligand id=7719/> (another third-generation irreversible EGFR inhibitor) which has confirmed brain penetrance, and which does not appear to cause the same dose-limiting toxicities that afflict dacomitinib. In April 2018 both the FDA and EMA accepted regulatory submissions (New Drug Application and Marketing Authorization Application respectively) for review of dacomitinib as a therapy for metastatic NSCLC with EGFR-activating mutations. The FDA granted Priority Review status for the submitted NDA. SARS-CoV-2: A high-throughput screen identified potential anti-SARS-CoV-2 activity in cell infection assays <Reference id=41947/>.
iupac name: (E)-N-[4-[(3-chloro-4-fluorophenyl)amino]-7-methoxyquinazolin-6-yl]-4-piperidin-1-ylbut-2-enamide
xref: CHEMBL2110732
synonym: Vizimpro®
synonym: PF00299804
synonym: PF 00299804
synonym: PF-00299804
approved: t
ligand name: dacomitinib
type: SyntheticOrganicLigand

carfilzomib
in ch i key: BLMPQMFVWMYDKT-NZTKNTHTSA-N
in ch i: InChI=1S/C40H57N5O7/c1-27(2)22-32(36(47)40(5)26-52-40)42-39(50)34(24-30-14-10-7-11-15-30)44-38(49)33(23-28(3)4)43-37(48)31(17-16-29-12-8-6-9-13-29)41-35(46)25-45-18-20-51-21-19-45/h6-15,27-28,31-34H,16-26H2,1-5H3,(H,41,46)(H,42,50)(H,43,48)(H,44,49)/t31-,32-,33-,34-,40+/m0/s1
comment: Carfilzomib is a tetrapeptide analogue of epoxomicin, an Actinomycete derived selective proteasome inhibitor <Reference id=24384/>.
iupac name: (2S)-4-methyl-N-[(2S)-1-[[(2S)-4-methyl-1-[(2R)-2-methyloxiran-2-yl]-1-oxopentan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]-4-phenylbutanoyl]amino]pentanamide
xref: CHEMBL451887
synonym: PR-171
synonym: Kyprolis®
approved: t
ligand name: carfilzomib
type: SyntheticOrganicLigand

zopolrestat
in ch i key: BCSVCWVQNOXFGL-UHFFFAOYSA-N
comment: Zopolrestat is an experimental aldose reductase inhibitor.
iupac name: 2-[4-oxo-3-[[5-(trifluoromethyl)-1,3-benzothiazol-2-yl]methyl]phthalazin-1-yl]acetic acid
xref: CHEMBL10372
synonym: CP-73850
approved: f
ligand name: zopolrestat
type: SyntheticOrganicLigand

zenarestat
in ch i key: SXONDGSPUVNZLO-UHFFFAOYSA-N
comment: Zenarestat is an experimental aldose reductase inhibitor.
iupac name: 2-[3-[(4-bromo-2-fluorophenyl)methyl]-7-chloro-2,4-dioxoquinazolin-1-yl]acetic acid
xref: CHEMBL10413
synonym: FK-366
synonym: FR-74366
approved: f
ligand name: zenarestat
type: SyntheticOrganicLigand

veliparib
canonical SMILES: NC(=O)c1cccc2c1nc([nH]2)C1(C)CCCN1
isomeric SMILES: NC(=O)c1cccc2c1nc([nH]2)[C@@]1(C)CCCN1
in ch i key: JNAHVYVRKWKWKQ-CYBMUJFWSA-N
in ch i: InChI=1S/C13H16N4O/c1-13(6-3-7-15-13)12-16-9-5-2-4-8(11(14)18)10(9)17-12/h2,4-5,15H,3,6-7H2,1H3,(H2,14,18)(H,16,17)/t13-/m1/s1
comment: Veliparib is an investigational poly ADP ribose polymerase (PARP) inhibitor. PARP inhibitors have potential for treating many diseases, including cancer.
iupac name: 2-[(2R)-2-methylpyrrolidin-2-yl]-1H-benzimidazole-4-carboxamide
xref: CHEMBL506871
synonym: ABT-888
approved: f
ligand name: veliparib
type: SyntheticOrganicLigand

tanaproget
canonical SMILES: N#Cc1ccc(n1C)c1ccc2c(c1)C(C)(C)OC(=S)N2
isomeric SMILES: N#Cc1ccc(n1C)c1ccc2c(c1)C(C)(C)OC(=S)N2
in ch i key: PYVFWTPEBMRKSR-UHFFFAOYSA-N
in ch i: InChI=1S/C16H15N3OS/c1-16(2)12-8-10(4-6-13(12)18-15(21)20-16)14-7-5-11(9-17)19(14)3/h4-8H,1-3H3,(H,18,21)
comment: Tanaproget is an experimental nonsteroidal progesterone receptor agonist.
iupac name: 5-(4,4-dimethyl-2-sulfanylidene-2,4-dihydro-1H-3,1-benzoxazin-6-yl)-1-methyl-1H-pyrrole-2-carbonitrile
xref: CHEMBL539163
synonym: NSP-989
approved: f
ligand name: tanaproget
type: SyntheticOrganicLigand

sorbinil
canonical SMILES: Fc1cc2C3(CCOc2cc1)NC(=O)NC3=O
isomeric SMILES: Fc1cc2[C@]3(CCOc2cc1)NC(=O)NC3=O
in ch i key: LXANPKRCLVQAOG-NSHDSACASA-N
in ch i: InChI=1S/C11H9FN2O3/c12-6-1-2-8-7(5-6)11(3-4-17-8)9(15)13-10(16)14-11/h1-2,5H,3-4H2,(H2,13,14,15,16)/t11-/m0/s1
comment: Chemical structure is derived from <Reference id=24377/>. Sorbinil is an experimental aldose reductase inhibitor.
iupac name: (4S)-6-fluorospiro[chroman-4,5'-imidazolidine]-2',4'-dione
xref: CHEMBL266497
synonym: CP-45634
approved: f
ligand name: sorbinil
type: SyntheticOrganicLigand

piritrexim
canonical SMILES: COc1ccc(cc1Cc1cnc2c(c1C)c(N)nc(n2)N)OC
isomeric SMILES: COc1ccc(cc1Cc1cnc2c(c1C)c(N)nc(n2)N)OC
in ch i key: VJXSSYDSOJBUAV-UHFFFAOYSA-N
in ch i: InChI=1S/C17H19N5O2/c1-9-11(6-10-7-12(23-2)4-5-13(10)24-3)8-20-16-14(9)15(18)21-17(19)22-16/h4-5,7-8H,6H2,1-3H3,(H4,18,19,20,21,22)
iupac name: 6-[(2,5-dimethoxyphenyl)methyl]-5-methylpyrido[3,2-e]pyrimidine-2,4-diamine
xref: CHEMBL7492
approved: f
ligand name: piritrexim
type: SyntheticOrganicLigand

gosogliptin
in ch i key: QWEWGXUTRTXFRF-KBPBESRZSA-N
in ch i: InChI=1S/C17H24F2N6O/c18-17(19)2-5-25(12-17)15(26)14-10-13(11-22-14)23-6-8-24(9-7-23)16-20-3-1-4-21-16/h1,3-4,13-14,22H,2,5-12H2/t13-,14-/m0/s1
iupac name: (3,3-difluoropyrrolidin-1-yl)-[(2S,4S)-4-(4-pyrimidin-2-ylpiperazin-1-yl)pyrrolidin-2-yl]methanone
xref: CHEMBL515387
synonym: PF-00734200
approved: f
ligand name: gosogliptin
type: SyntheticOrganicLigand

metoprine
canonical SMILES: Nc1nc(C)c(c(n1)N)c1ccc(c(c1)Cl)Cl
isomeric SMILES: Nc1nc(C)c(c(n1)N)c1ccc(c(c1)Cl)Cl
in ch i key: VQJHOPSWBGJHQS-UHFFFAOYSA-N
in ch i: InChI=1S/C11H10Cl2N4/c1-5-9(10(14)17-11(15)16-5)6-2-3-7(12)8(13)4-6/h2-4H,1H3,(H4,14,15,16,17)
iupac name: 5-(3,4-DICHLOROPHENYL)-6-METHYLPYRIMIDINE-2,4-DIAMINE
xref: CHEMBL264373
synonym: methodichlorophen
synonym: DDMP
synonym: NSC-19494
synonym: BW-197U
synonym: NSC7364
synonym: TCMDC-123931
approved: f
ligand name: metoprine
type: SyntheticOrganicLigand

lidorestat
in ch i key: KYHVTMFADJNSGS-UHFFFAOYSA-N
comment: Lidorestat is an experimental aldose reductase inhibitor. <Reference id=24372/><Reference id=24373/>.
iupac name: 2-[3-[(4,5,7-trifluoro-1,3-benzothiazol-2-yl)methyl]indol-1-yl]acetic acid
xref: CHEMBL363387
synonym: IDD-676
synonym: IDD-000676-01
approved: f
ligand name: lidorestat
type: SyntheticOrganicLigand

ilomastat
in ch i key: NITYDPDXAAFEIT-DYVFJYSZSA-N
in ch i: InChI=1S/C20H28N4O4/c1-12(2)8-13(10-18(25)24-28)19(26)23-17(20(27)21-3)9-14-11-22-16-7-5-4-6-15(14)16/h4-7,11-13,17,22,28H,8-10H2,1-3H3,(H,21,27)(H,23,26)(H,24,25)/t13-,17+/m1/s1
comment: Ilomastat is a broad-spectrum inhibitor of group M10 and M12 metallopeptidases.
iupac name: (2R)-N'-hydroxy-N-[(2S)-3-(1H-indol-3-yl)-1-methylamino-1-oxopropan-2-yl]-2-(2-methylpropyl)butanediamide
xref: CHEMBL19611
synonym: Galardin
synonym: GM 6001
synonym: CS 610
approved: f
ligand name: ilomastat
type: SyntheticOrganicLigand

eribaxaban
in ch i key: QQBKAVAGLMGMHI-WIYYLYMNSA-N
comment: Eribaxaban is a Pfizer experimental anticoagulant which targets activated factor X (FXa) <Reference id=24366/><Reference id=24367/>. It has reached Phase 2 for prevention of venous thromboembolism in knee replacement
iupac name: (2R,4R)-N-(4-chlorophenyl)-N'-[2-fluoro-4-(2-oxopyridin-1-yl)phenyl]-4-methoxypyrrolidine-1,2-dicarboxamide
xref: CHEMBL476186
synonym: PD-0348292
approved: f
ligand name: eribaxaban
type: SyntheticOrganicLigand

cilomilast
in ch i key: CFBUZOUXXHZCFB-OYOVHJISSA-N
in ch i: InChI=1S/C20H25NO4/c1-24-17-7-6-15(12-18(17)25-16-4-2-3-5-16)20(13-21)10-8-14(9-11-20)19(22)23/h6-7,12,14,16H,2-5,8-11H2,1H3,(H,22,23)/t14-,20-
comment: There is some ambiguity in the literature and on other database as to the exact structure of Cilomilast. The structure shown here matches that of the INN document, but the compound is represented on PubChem without specified stereochemistry by CID 151170.
iupac name: (1s,4s)-4-cyano-4-[3-(cyclopentyloxy)-4-methoxyphenyl]cyclohexane-1-carboxylic acid
xref: CHEMBL511115
synonym: Ariflo
synonym: SB-207499
approved: f
ligand name: cilomilast
type: SyntheticOrganicLigand

brequinar
in ch i key: PHEZJEYUWHETKO-UHFFFAOYSA-N
in ch i: InChI=1S/C23H15F2NO2/c1-13-21(23(27)28)18-12-16(24)10-11-20(18)26-22(13)15-8-6-14(7-9-15)17-4-2-3-5-19(17)25/h2-12H,1H3,(H,27,28)
comment: Brequinar inhibits dihydroorotate dehydrogenase (DHODH), the fourth enzyme in the de novo pyrimidine biosynthesis pathway <Reference id=40099/>, and it depletes cells of the precursors that are critical for RNA and DNA synthesis <Reference id=40098/>. It was developed for potential anti-neoplastic activity. The drug exhibits anti-neoplastic activity against refractory solid tumours in preclinical models, with continuous treatment being necessary to effectively deplete pyrimidine pools in the cancer cells and cause tumour inhibition <Reference id=24363/>.
iupac name: 6-fluoro-2-[4-(2-fluorophenyl)phenyl]-3-methylquinoline-4-carboxylic acid
xref: CHEMBL38434
synonym: DUP785
synonym: DUP-785
synonym: NSC 368390
synonym: NSC-368390
synonym: NSC368390
approved: f
ligand name: brequinar
type: SyntheticOrganicLigand

aleglitazar
in ch i key: DAYKLWSKQJBGCS-NRFANRHFSA-N
in ch i: InChI=1S/C24H23NO5S/c1-15-19(25-23(30-15)16-6-4-3-5-7-16)10-12-29-20-9-8-17(14-21(28-2)24(26)27)22-18(20)11-13-31-22/h3-9,11,13,21H,10,12,14H2,1-2H3,(H,26,27)/t21-/m0/s1
comment: Aleglitazar is a dual PPARα/δ agonist, or 'glitazar'.
iupac name: (2S)-2-methoxy-3-[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]-1-benzothiophen-7-yl]propanoic acid
xref: CHEMBL519504
synonym: Ro-0728804
synonym: Alecardio
synonym: R-1439
approved: f
ligand name: aleglitazar
type: SyntheticOrganicLigand

compound 36 [PMID: 17936624]
canonical SMILES: COc1cc(OC)cc(c1)c1ncc2c(c1)nc(cc2)C
isomeric SMILES: COc1cc(OC)cc(c1)c1ncc2c(c1)nc(cc2)C
in ch i key: AWGMVVADCJSVIO-UHFFFAOYSA-N
in ch i: InChI=1S/C17H16N2O2/c1-11-4-5-12-10-18-16(9-17(12)19-11)13-6-14(20-2)8-15(7-13)21-3/h4-10H,1-3H3
iupac name: 7-(3,5-dimethoxyphenyl)-2-methyl-1,6-naphthyridine
xref: CHEMBL238344
approved: f
ligand name: compound 36 [PMID: 17936624]
type: SyntheticOrganicLigand

raltitrexed
in ch i key: IVTVGDXNLFLDRM-HNNXBMFYSA-N
in ch i: InChI=1S/C21H22N4O6S/c1-11-22-14-4-3-12(9-13(14)19(28)23-11)10-25(2)17-7-6-16(32-17)20(29)24-15(21(30)31)5-8-18(26)27/h3-4,6-7,9,15H,5,8,10H2,1-2H3,(H,24,29)(H,26,27)(H,30,31)(H,22,23,28)/t15-/m0/s1
comment: Raltitrexed is an antimetabolite drug.
iupac name: (2S)-2-[[5-[methyl-[(2-methyl-4-oxo-1H-quinazolin-6-yl)methyl]amino]thiophene-2-carbonyl]amino]pentanedioic acid
xref: CHEMBL225071
synonym: ZD1694
synonym: ICI-D-1694
synonym: Tomudex®
approved: t
ligand name: raltitrexed
type: SyntheticOrganicLigand

phenacetin
canonical SMILES: CCOc1ccc(cc1)NC(=O)C
isomeric SMILES: CCOc1ccc(cc1)NC(=O)C
in ch i key: CPJSUEIXXCENMM-UHFFFAOYSA-N
in ch i: InChI=1S/C10H13NO2/c1-3-13-10-6-4-9(5-7-10)11-8(2)12/h4-7H,3H2,1-2H3,(H,11,12)
comment: This drug is rapidly metabolised to <Ligand id=5239/>, (aka acetaminophen), so it is conceivable that some of its therapeutic activity is attributable this major metabolite.
iupac name: N-(4-Ethoxyphenyl)acetamide
xref: CHEMBL16073
synonym: acetophenetidin
approved: t
ligand name: phenacetin
type: SyntheticOrganicLigand

nimesulide
canonical SMILES: [O-][N+](=O)c1ccc(c(c1)Oc1ccccc1)NS(=O)(=O)C
isomeric SMILES: [O-][N+](=O)c1ccc(c(c1)Oc1ccccc1)NS(=O)(=O)C
in ch i key: HYWYRSMBCFDLJT-UHFFFAOYSA-N
in ch i: InChI=1S/C13H12N2O5S/c1-21(18,19)14-12-8-7-10(15(16)17)9-13(12)20-11-5-3-2-4-6-11/h2-9,14H,1H3
comment: Nimesulide is a non-steroidal anti-inflammatory drug (NSAID), with analgesic and antipyretic properties.
iupac name: N-[4-nitro-2-(phenoxy)phenyl]methanesulfonamide
xref: CHEMBL56367
synonym: R-805
synonym: Mesulid
synonym: Nimed
synonym: Aulin
synonym: Fansidol
synonym: Flogovital
synonym: Nidol
synonym: Nide
approved: t
ligand name: nimesulide
type: SyntheticOrganicLigand

iodipamide
in ch i key: FFINMCNLQNTKLU-UHFFFAOYSA-N
in ch i: InChI=1S/C20H14I6N2O6/c21-7-5-9(23)17(15(25)13(7)19(31)32)27-11(29)3-1-2-4-12(30)28-18-10(24)6-8(22)14(16(18)26)20(33)34/h5-6H,1-4H2,(H,27,29)(H,28,30)(H,31,32)(H,33,34)
comment: Iodipamide is an ionic radiopaque contrast agent.
iupac name: 3-[[6-[(3-carboxy-2,4,6-triiodophenyl)amino]-6-oxohexanoyl]amino]-2,4,6-triiodobenzoic acid
xref: CHEMBL1165268
synonym: adipiodone meglumine
synonym: radio-cholografin
synonym: Cholografin
synonym: Cholospect
synonym: Transbilix
synonym: iodipamic acid
approved: t
ligand name: iodipamide
type: SyntheticOrganicLigand

ibudilast
canonical SMILES: CC(C(=O)c1c(nn2c1cccc2)C(C)C)C
isomeric SMILES: CC(C(=O)c1c(nn2c1cccc2)C(C)C)C
in ch i key: ZJVFLBOZORBYFE-UHFFFAOYSA-N
in ch i: InChI=1S/C14H18N2O/c1-9(2)13-12(14(17)10(3)4)11-7-5-6-8-16(11)15-13/h5-10H,1-4H3
comment: Ibudilast is a phosphodiesterase (PDE) inhibitor antiinflammatory drug. See the Biological activity tab for affinity data across a range of PDE isozymes.
iupac name: 2-methyl-1-(2-propan-2-ylpyrazolo[1,5-a]pyridin-3-yl)propan-1-one
xref: CHEMBL19449
synonym: AV-411
synonym: MN-166
synonym: KC-404
synonym: Kyorin
synonym: Eyevinal
synonym: Ketas®
approved: t
ligand name: ibudilast
type: SyntheticOrganicLigand

ethcathinone
canonical SMILES: CCNC(C(=O)c1ccccc1)C
isomeric SMILES: CCNC(C(=O)c1ccccc1)C
in ch i key: LYMHIBZGTAPASQ-UHFFFAOYSA-N
in ch i: InChI=1S/C11H15NO/c1-3-12-9(2)11(13)10-7-5-4-6-8-10/h4-9,12H,3H2,1-2H3
comment: Ethcathinone is the active form of the approved prodrug diethylpropion.
iupac name: 2-ethylamino-1-phenylpropan-1-one
xref: CHEMBL3298876
synonym: ethylpropion
synonym: ETH-CAT
approved: f
ligand name: ethcathinone
type: SyntheticOrganicLigand

ceritinib
in ch i key: VERWOWGGCGHDQE-UHFFFAOYSA-N
comment: Ceritinib is a novel, highly selective, second generation ALK inhibitor <Reference id=24315/>.
iupac name: 5-chloro-2-N-(5-methyl-4-piperidin-4-yl-2-propan-2-yloxyphenyl)-4-N-(2-propan-2-ylsulfonylphenyl)pyrimidine-2,4-diamine
xref: CHEMBL2403108
synonym: compound 15b [PMID 23742252]
synonym: NVP-LDK378-NX
synonym: LDK378
synonym: Zykadia®
approved: t
ligand name: ceritinib
type: SyntheticOrganicLigand

tasimelteon
canonical SMILES: CCC(=O)NCC1CC1c1cccc2c1CCO2
isomeric SMILES: CCC(=O)NC[C@@H]1C[C@H]1c1cccc2c1CCO2
in ch i key: PTOIAAWZLUQTIO-GXFFZTMASA-N
in ch i: InChI=1S/C15H19NO2/c1-2-15(17)16-9-10-8-13(10)11-4-3-5-14-12(11)6-7-18-14/h3-5,10,13H,2,6-9H2,1H3,(H,16,17)/t10-,13+/m0/s1
comment: Tasimelteon is a melatonin receptor agonist, activating both the MT1 and MT2 receptor subtypes equipotently. <Ligand id=1356/> and <Ligand id=198/> are also melatonin receptor agonist class drugs.
iupac name: N-[[(1R,2R)-2-(2,3-dihydro-1-benzofuran-4-yl)cyclopropyl]methyl]propanamide
xref: CHEMBL2103822
synonym: VEC-162
synonym: BMS-214778
synonym: Hetlioz®
approved: t
ligand name: tasimelteon
type: SyntheticOrganicLigand

acelarin
in ch i key: NHTKGYOMICWFQZ-BSMFTPRPSA-N
comment: Acelerin is a candidate pro-drug. The proposed route to the active monophosphate form is depicted in Scheme 4 in <Reference id=24220/>. Acerlarin is an analogue of <Ligand id=4793/>, the main therapeutic used to treat pancreatic cancer. Acelarin is termed a ProTide, and structurally is gemcitabine with an attached phosphoramidate group. The aim of this chemical modification is to achieve improved cellular delivery of the activated drug, overcoming resistance mechanisms and protecting against enzymatic breakdown to toxic byproducts <Reference id=24220/>, and hopefully achieving better disease response. The chemical structure depicted here was drawn from <Reference id=24220/> where acelerin is compound 6f. Acelarin is the first ProTide to reach clinical trial and is only one member of a large development pipeline covering many nucleoside anti-metabolite anti-neoplastic drugs.
iupac name: benzyl (2S)-2-[({[(2R,3S,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-4,4-difluoro-3-hydroxyoxolan-2-yl]methoxy}(phenoxy)phosphoryl)amino]propanoate
synonym: NUC-1031
approved: f
ligand name: acelarin
type: SyntheticOrganicLigand

lixisenatide
in ch i key: XVVOERDUTLJJHN-IAEQDCLQSA-N
comment: Lixisenatide is a GLP-1 peptide mimetic. The sequence for this drug differs from native GLP-1 as depicted in <Reference id=24217/>, and is largely based on the sequence of exendin-4 from the Gila monster (Heloderma suspectum). Lixisenatide is licensed as a once-daily mealtime GLP-1 receptor agonist administered by sub-cuteneous injection.
xref: CHEMBL2108336
synonym: Adlyxin®
synonym: AVE-0010
synonym: Lyxumia®
approved: t
ligand name: lixisenatide
type: PeptideLigand

ribociclib
in ch i key: RHXHGRAEPCAFML-UHFFFAOYSA-N
in ch i: InChI=1S/C23H30N8O/c1-29(2)22(32)19-13-16-14-26-23(28-21(16)31(19)17-5-3-4-6-17)27-20-8-7-18(15-25-20)30-11-9-24-10-12-30/h7-8,13-15,17,24H,3-6,9-12H2,1-2H3,(H,25,26,27,28)
comment: Ribociclib is a selective, orally available inhibitor of the cyclin-dependent kinases CDK4 and CDK6 <Reference id=15289/><Reference id=32496/>.
iupac name: 7-cyclopentyl-N,N-dimethyl-2-{[5-(piperazin-1-yl)pyridin-2-yl]amino}-7H-pyrrolo[2,3-d]pyrimidine-6-carboxamide
synonym: LEE011
synonym: example 74 [US8962630]
synonym: Kisqali®
synonym: LEE-011
approved: t
ligand name: ribociclib
type: SyntheticOrganicLigand

abemaciclib
in ch i key: UZWDCWONPYILKI-UHFFFAOYSA-N
in ch i: InChI=1S/C27H32F2N8/c1-5-35-8-10-36(11-9-35)16-19-6-7-24(30-14-19)33-27-31-15-22(29)25(34-27)20-12-21(28)26-23(13-20)37(17(2)3)18(4)32-26/h6-7,12-15,17H,5,8-11,16H2,1-4H3,(H,30,31,33,34)
comment: Abemaciclib (LY2835219) is a selective ATP-competitive inhibitor of the cyclin-dependent kinases CDK4 and CDK6 <Reference id=24201/>.
iupac name: N-[5-[(4-ethylpiperazin-1-yl)methyl]pyridin-2-yl]-5-fluoro-4-(7-fluoro-2-methyl-3-propan-2-ylbenzimidazol-5-yl)pyrimidin-2-amine
xref: CHEMBL3301610
synonym: Verzenios®
synonym: LY2835219
synonym: Verzenio®
synonym: HY-16297A
synonym: CS-1230
synonym: LY 2835219
synonym: LY-2835219
approved: t
ligand name: abemaciclib
type: SyntheticOrganicLigand

RS-100329
in ch i key: RCOBWVAGWYRNHZ-UHFFFAOYSA-N
in ch i: InChI=1S/C20H25F3N4O3/c1-15-13-24-19(29)27(18(15)28)8-4-7-25-9-11-26(12-10-25)16-5-2-3-6-17(16)30-14-20(21,22)23/h2-3,5-6,13H,4,7-12,14H2,1H3,(H,24,29)
comment: RS-100329 is an α1A-adrenoceptor selective antagonist .
iupac name: 5-methyl-3-[3-[4-[2-(2,2,2-trifluoroethoxy)phenyl]piperazin-1-yl]propyl]-1H-pyrimidine-2,4-dione
xref: CHEMBL56331
synonym: RS100329
synonym: RS 100329
approved: f
ligand name: RS-100329
type: SyntheticOrganicLigand

palbociclib
in ch i key: AHJRHEGDXFFMBM-UHFFFAOYSA-N
in ch i: InChI=1S/C24H29N7O2/c1-15-19-14-27-24(28-20-8-7-18(13-26-20)30-11-9-25-10-12-30)29-22(19)31(17-5-3-4-6-17)23(33)21(15)16(2)32/h7-8,13-14,17,25H,3-6,9-12H2,1-2H3,(H,26,27,28,29)
comment: Palbociclib is a selective inhibitor of the cyclin-dependent kinases CDK4 and CDK6 <Reference id=24188/><Reference id=24189/><Reference id=24194/>. This kinase inhibitor has anti-tumour activity in several tumour models <Reference id=24189/><Reference id=24191/><Reference id=24188/><Reference id=24192/><Reference id=24193/>. The pharmaceutical formulation contains palbociclib isethionate (PubChem CID 11478676).
iupac name: 6-acetyl-8-cyclopentyl-5-methyl-2-[(5-piperazin-1-ylpyridin-2-yl)amino]pyrido[6,5-d]pyrimidin-7-one
xref: CHEMBL189963
synonym: PD-0332991
synonym: PD0332991
synonym: Ibrance®
synonym: PD 0332991
approved: t
ligand name: palbociclib
type: SyntheticOrganicLigand

dinaciclib
isomeric SMILES: OCC[C@@H]1CCCCN1c1cc(NCc2ccc[n+](c2)[O-])n2c(n1)c(CC)cn2
in ch i key: PIMQWRZWLQKKBJ-SFHVURJKSA-N
in ch i: InChI=1S/C21H28N6O2/c1-2-17-14-23-27-19(22-13-16-6-5-9-25(29)15-16)12-20(24-21(17)27)26-10-4-3-7-18(26)8-11-28/h5-6,9,12,14-15,18,22,28H,2-4,7-8,10-11,13H2,1H3/t18-/m0/s1
comment: Dinaciclib is a potent cyclin-dependent kinase (CDK) inhibitor, inhibiting the CDK4 and 6 isoforms <Reference id=24187/>. Dinaciclib has also been reported to interact with the acetyl-lysine recognition domain of the bromodomain testis-specific protein BRDT <Reference id=24187/>. BRDT is a member of the BET family of bromodomain-containing proteins which are considered to be atypical kinases. SARS-CoV-2: SARS-CoV-2 may regulate the host cell cycle to enhance viral replication, and in vitro phosphoproteomics analysis suggests that viral hijacking of the CDK signalling pathway may, at least in part, mediate this mechanism <Reference id=39830/>. Pharmacological inhibition of the CDK pathway with dinaciclib has anti-SARS-CoV-2 activity in two model cells lines, A549-ACE2 cells (IC50 32 nM) and Vero E6 cells (IC50 127 nM).
iupac name: 2-[(2S)-1-[3-ethyl-7-[(1-oxidopyridin-1-ium-3-yl)methylamino]pyrazolo[1,5-a]pyrimidin-5-yl]piperidin-2-yl]ethanol
xref: CHEMBL2103840
synonym: SCH727965
approved: f
ligand name: dinaciclib
type: SyntheticOrganicLigand

oxaprozin
canonical SMILES: OC(=O)CCc1nc(c(o1)c1ccccc1)c1ccccc1
isomeric SMILES: OC(=O)CCc1nc(c(o1)c1ccccc1)c1ccccc1
in ch i key: OFPXSFXSNFPTHF-UHFFFAOYSA-N
in ch i: InChI=1S/C18H15NO3/c20-16(21)12-11-15-19-17(13-7-3-1-4-8-13)18(22-15)14-9-5-2-6-10-14/h1-10H,11-12H2,(H,20,21)
comment: Oxaprozin is a nonsteroidal anti-inflammatory drug (NSAID).
iupac name: 3-(diphenyl-1,3-oxazol-2-yl)propanoic acid
xref: CHEMBL1071
synonym: Oxaprozin
synonym: Daypro Alta
synonym: Daypro®
synonym: WY-21743
approved: t
ligand name: oxaprozin
type: SyntheticOrganicLigand

EPZ004777
in ch i key: WXRGFPHDRFQODR-ICLZECGLSA-N
in ch i: InChI=1S/C28H41N7O4/c1-17(2)34(13-6-12-30-27(38)33-19-9-7-18(8-10-19)28(3,4)5)15-21-22(36)23(37)26(39-21)35-14-11-20-24(29)31-16-32-25(20)35/h7-11,14,16-17,21-23,26,36-37H,6,12-13,15H2,1-5H3,(H2,29,31,32)(H2,30,33,38)/t21-,22-,23-,26-/m1/s1
comment: EPZ004777 is an analogue of the enzyme co-factor S-adenosyl methionine (SAM). SAM is the classical methyl donor for methyltrasferases.
iupac name: 3-[3-({[(2R,3S,4R,5R)-5-{4-amino-7H-pyrrolo[2,3-d]pyrimidin-7-yl}-3,4-dihydroxyoxolan-2-yl]methyl}(propan-2-yl)amino)propyl]-1-(4-tert-butylphenyl)urea
xref: CHEMBL2169919
synonym: EPZ-004777
synonym: EPZ 004777
approved: f
ligand name: EPZ004777
type: SyntheticOrganicLigand

rilapladib
in ch i key: NNBGCSGCRSCFEA-UHFFFAOYSA-N
comment: Lipoprotein-associated phospholipase A2 (Lp-PLA2, PLA2-G7) inhibitors such as rilapladib and <Ligand id=6696/> have been evaluated in clinical trials: darapladib for coronary heart disease, and rilapladib for Alzheimer's disease. Compounds of different chemotypes are being explored as tools to further optimise the pharmacological modulation of PLA2-G7 as a target for clinical intervention- see also <Ligand id=9796/> (tool compound).
xref: CHEMBL2104981
synonym: SB 659032
approved: f
ligand name: rilapladib
type: SyntheticOrganicLigand

BRD9539
in ch i key: WPXMEOBILYVKBC-UHFFFAOYSA-N
in ch i: InChI=1S/C24H21N3O3/c28-22(18-11-5-2-6-12-18)26-24-25-20-16-19(23(29)30)13-14-21(20)27(24)15-7-10-17-8-3-1-4-9-17/h1-6,8-9,11-14,16H,7,10,15H2,(H,29,30)(H,25,26,28)
comment: BRD9539 may be the active form of BRD4770 in vivo (see <Reference id=24139/>) .
iupac name: 2-benzamido-1-(3-phenylpropyl)-1H-1,3-benzodiazole-5-carboxylic acid
synonym: BRD-9539
synonym: BRD 9539
approved: f
ligand name: BRD9539
type: SyntheticOrganicLigand

tubacin
in ch i key: BHUZLJOUHMBZQY-YXQOSMAKSA-N
in ch i: InChI=1S/C41H43N3O7S/c45-26-28-17-19-29(20-18-28)35-25-34(27-52-41-43-38(30-11-5-3-6-12-30)39(51-41)31-13-7-4-8-14-31)49-40(50-35)32-21-23-33(24-22-32)42-36(46)15-9-1-2-10-16-37(47)44-48/h3-8,11-14,17-24,34-35,40,45,48H,1-2,9-10,15-16,25-27H2,(H,42,46)(H,44,47)/t34-,35+,40+/m1/s1
comment: Tubacin is a small-molecule inhibitor of HDAC6 <Reference id=24130/>.
iupac name: N-[4-[(2R,4R,6S)-4-[[4,5-di(phenyl)-1,3-oxazol-2-yl]sulfanylmethyl]-6-[4-(hydroxymethyl)phenyl]-1,3-dioxan-2-yl]phenyl]-N'-hydroxyoctanediamide
xref: CHEMBL356769
synonym: AC1O7Y2P
approved: f
ligand name: tubacin
type: SyntheticOrganicLigand

apremilast
in ch i key: IMOZEMNVLZVGJZ-QGZVFWFLSA-N
in ch i: InChI=1S/C22H24N2O7S/c1-5-31-19-11-14(9-10-18(19)30-3)17(12-32(4,28)29)24-21(26)15-7-6-8-16(23-13(2)25)20(15)22(24)27/h6-11,17H,5,12H2,1-4H3,(H,23,25)/t17-/m1/s1
comment: Apremilast is an oral small molecule phosphodiesterase 4 (PDE4) inhibitor <Reference id=24124/><Reference id=24123/> (additional comment in <Reference id=24122/>). It is selective for PDE4 over other PDE isozymes, but non-selective over PDE4 isoforms <Reference id=32860/>.
iupac name: N-[2-[(1S)-1-(3-ethoxy-4-methoxyphenyl)-2-methylsulfonylethyl]-1,3-dioxoisoindol-4-yl]acetamide
xref: CHEMBL514800
synonym: CC-10004
synonym: Otezla®
approved: t
ligand name: apremilast
type: SyntheticOrganicLigand

AQW051
canonical SMILES: Cc1ccc(cc1)c1ccc(cn1)OC1CN2CCC1CC2
isomeric SMILES: Cc1ccc(cc1)c1ccc(cn1)O[C@H]1CN2CCC1CC2
in ch i key: NPDLTEZXGWRMLQ-IBGZPJMESA-N
in ch i: InChI=1S/C19H22N2O/c1-14-2-4-15(5-3-14)18-7-6-17(12-20-18)22-19-13-21-10-8-16(19)9-11-21/h2-7,12,16,19H,8-11,13H2,1H3/t19-/m0/s1
comment: AQW 051 is an α7 nicotinic acetylcholine receptor (nAChR) agonist from Novartis for the oral treatment of cognitive deficits in schizophrenia, Alzheimer's, and Parkinson's diseases. Structure first disclosed at March 2014 ACS meeting. The (3S) version is CID 71553840
iupac name: (3R)-3-{[6-(4-methylphenyl)pyridin-3-yl]oxy}-1-azabicyclo[2.2.2]octane
approved: f
ligand name: AQW051
type: SyntheticOrganicLigand

KB-74935
in ch i key: OMWNFYWEMXUREB-LLVKDONJSA-N
iupac name: 3-chloro-4-[(2R)-4-[4-fluoro-2-(trifluoromethyl)phenyl]-2-methylpiperazin-1-yl]sulfonylbenzamide
xref: CHEMBL550175
synonym: KB 74935
approved: f
ligand name: KB-74935
type: SyntheticOrganicLigand

ASS234
in ch i key: ADCBAOTWERXLAP-UHFFFAOYSA-N
in ch i: InChI=1S/C29H37N3O/c1-4-16-30(2)23-27-20-26-21-28(12-13-29(26)31(27)3)33-19-8-11-24-14-17-32(18-15-24)22-25-9-6-5-7-10-25/h1,5-7,9-10,12-13,20-21,24H,8,11,14-19,22-23H2,2-3H3
iupac name: N-[[5-[3-(1-benzylpiperidin-4-yl)propoxy]-1-methylindol-2-yl]methyl]-N-methylprop-2-yn-1-amine
xref: CHEMBL1929421
approved: f
ligand name: ASS234
type: SyntheticOrganicLigand

trichlormethiazide
in ch i key: LMJSLTNSBFUCMU-UHFFFAOYSA-N
comment: Trichlormethiazide is a diuretic.
iupac name: 6-chloro-3-(dichloromethyl)-1,1-dioxo-3,4-dihydro-2H-1λ6,2,4-benzothiadiazine-7-sulfonamide
xref: CHEMBL1054
synonym: Metahydrin
synonym: Trichlorex
synonym: Trichlormas
synonym: Naqua®
approved: t
ligand name: trichlormethiazide
type: SyntheticOrganicLigand

sofosbuvir
in ch i key: TTZHDVOVKQGIBA-IQWMDFIBSA-N
in ch i: InChI=1S/C22H29FN3O9P/c1-13(2)33-19(29)14(3)25-36(31,35-15-8-6-5-7-9-15)32-12-16-18(28)22(4,23)20(34-16)26-11-10-17(27)24-21(26)30/h5-11,13-14,16,18,20,28H,12H2,1-4H3,(H,25,31)(H,24,27,30)/t14-,16+,18+,20+,22+,36-/m0/s1
comment: Sofosbuvir is a nucleotide analogue whose action inhibits hepatitis C virus (HCV) NS5B RNA-dependent RNA polymerase. It acts as a chain terminator to limit viral RNA replication. Sofosbuvir is on the World Health Organisation's List of Essential Medicines. Click here to access the pdf version of the WHO's 21st Essential Medicines list (2019).
iupac name: propan-2-yl (2S)-2-[[[(2R,3R,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-4-fluoro-3-hydroxy-4-methyloxolan-2-yl]methoxy-phenoxyphosphoryl]amino]propanoate
xref: CHEMBL1259059
synonym: GI-7977
synonym: PSI 7977
synonym: Sovaldi®
approved: t
ligand name: sofosbuvir
type: SyntheticOrganicLigand

simeprevir
in ch i key: JTZZSQYMACOLNN-VDWJNHBNSA-N
in ch i: InChI=1S/C38H47N5O7S2/c1-21(2)30-20-51-35(40-30)29-18-32(26-13-14-31(49-5)22(3)33(26)39-29)50-24-16-27-28(17-24)36(45)43(4)15-9-7-6-8-10-23-19-38(23,41-34(27)44)37(46)42-52(47,48)25-11-12-25/h8,10,13-14,18,20-21,23-25,27-28H,6-7,9,11-12,15-17,19H2,1-5H3,(H,41,44)(H,42,46)/b10-8-/t23-,24-,27-,28-,38-/m1/s1
comment: Simeprevir is a hepatitis C virus NS3/4A protease inhibitor.
xref: CHEMBL501849
synonym: TMC 435
synonym: TMC 435350
synonym: TMC-435
synonym: TMC435
synonym: Olysio®
synonym: simeprevir sodium
approved: t
ligand name: simeprevir
type: SyntheticOrganicLigand

luliconazole
canonical SMILES: N#CC(=C1SCC(S1)c1ccc(cc1Cl)Cl)n1cncc1
isomeric SMILES: N#C/C(=C/1/SC[C@H](S1)c1ccc(cc1Cl)Cl)/n1cncc1
in ch i key: YTAOBBFIOAEMLL-REQDGWNSSA-N
in ch i: InChI=1S/C14H9Cl2N3S2/c15-9-1-2-10(11(16)5-9)13-7-20-14(21-13)12(6-17)19-4-3-18-8-19/h1-5,8,13H,7H2/b14-12+/t13-/m0/s1
comment: Luliconazole is an imidazole antifungal drug.
iupac name: (2E)-2-[(4R)-4-(2,4-dichlorophenyl)-1,3-dithiolan-2-ylidene]-2-imidazol-1-ylacetonitrile
xref: CHEMBL2105689
synonym: NND-502
synonym: PR-2699
synonym: Luzu®
synonym: Lulicon®
approved: t
ligand name: luliconazole
type: SyntheticOrganicLigand

dolutegravir
in ch i key: RHWKPHLQXYSBKR-BMIGLBTASA-N
comment: Dolutegravir is an HIV viral integrase inhibitor class drug.
iupac name: (4R,12aS)-N-[(2,4-difluorophenyl)methyl]-7-hydroxy-4-methyl-6,8-dioxo-3,4,12,12a-tetrahydro-2H-pyrido[5,6]pyrazino[2,6-b][1,3]oxazine-9-carboxamide
xref: CHEMBL1229211
synonym: GSK1349572
synonym: GSK-1349572
synonym: GSK 1349572
synonym: S-349572
synonym: Tivicay®
approved: t
ligand name: dolutegravir
type: SyntheticOrganicLigand

orphenadrine
canonical SMILES: CN(CCOC(c1ccccc1C)c1ccccc1)C
isomeric SMILES: CN(CCOC(c1ccccc1C)c1ccccc1)C
in ch i key: QVYRGXJJSLMXQH-UHFFFAOYSA-N
in ch i: InChI=1S/C18H23NO/c1-15-9-7-8-12-17(15)18(20-14-13-19(2)3)16-10-5-4-6-11-16/h4-12,18H,13-14H2,1-3H3
comment: Orphenadrine is a muscle relaxant. Marketed formulations contain the citrate salt (PubChem CID 83823) or the hydrochloride (PubChem CID 9568)..
xref: CHEMBL900
synonym: Disipal
synonym: Norflex
synonym: Norgesic
synonym: Invagesic®
approved: t
ligand name: orphenadrine
type: SyntheticOrganicLigand

mipomersen
in ch i key: TZRFSLHOCZEXCC-HIVFKXHNSA-A
comment: MOE in the nucleotide image denotes nucleosides with 2'-O-(2-methoxyethyl) modification. The drug formulation contains the sodium salt, mipomersen sodium (CHEMBL2107849).
xref: CHEMBL2219536
synonym: ISIS 301012 parent acid
synonym: Kynamro®
approved: t
ligand name: mipomersen
type: SyntheticOrganicLigand

neurotensin-(8-13)
in ch i key: DQDBCHHEIKQPJD-ODKJCKIQSA-N
in ch i: InChI=1S/C38H64N12O8/c1-5-22(4)30(34(55)48-28(36(57)58)19-21(2)3)49-32(53)27(20-23-12-14-24(51)15-13-23)47-33(54)29-11-8-18-50(29)35(56)26(10-7-17-45-38(42)43)46-31(52)25(39)9-6-16-44-37(40)41/h12-15,21-22,25-30,51H,5-11,16-20,39H2,1-4H3,(H,46,52)(H,47,54)(H,48,55)(H,49,53)(H,57,58)(H4,40,41,44)(H4,42,43,45)/t22-,25-,26-,27-,28-,29-,30-/m0/s1
comment: Truncated analogue of endogenous peptide neurotensin.
approved: f
ligand name: neurotensin-(8-13)
type: PeptideLigand

JDTic
in ch i key: ZLVXBBHTMQJRSX-VMGNSXQWSA-N
in ch i: InChI=1S/C28H39N3O3/c1-18(2)26(30-27(34)25-13-20-8-9-24(33)12-21(20)15-29-25)17-31-11-10-28(4,19(3)16-31)22-6-5-7-23(32)14-22/h5-9,12,14,18-19,25-26,29,32-33H,10-11,13,15-17H2,1-4H3,(H,30,34)/t19-,25+,26+,28+/m0/s1
comment: JDTic is a potent and selective κ opioid receptor antagonist <Reference id=31011/>.
iupac name: (3R)-7-hydroxy-N-[(2S)-1-[(3R,4R)-4-(3-hydroxyphenyl)-3,4-dimethylpiperidin-1-yl]-3-methylbutan-2-yl]-1,2,3,4-tetrahydroisoquinoline-3-carboxamide
xref: CHEMBL415247
synonym: compound 10 [PMID: 11495579]
approved: f
ligand name: JDTic
type: SyntheticOrganicLigand

compound 24 [PMID: 16451050]
in ch i key: MAKMQGKJURAJEN-RUZDIDTESA-N
in ch i: InChI=1S/C27H35N3O2/c31-26(25-12-6-17-30(25)20-22-8-2-1-3-9-22)28-15-7-16-29-18-13-27(14-19-29)24-11-5-4-10-23(24)21-32-27/h1-5,8-11,25H,6-7,12-21H2,(H,28,31)/t25-/m1/s1
comment: compound 24 [PMID: 16451050] is a rationally designed NOP receptor antagonist <Reference id=28652/>.
iupac name: (2R)-1-(phenylmethyl)-N-(3-spiro[1H-2-benzofuran-3,4'-piperidine]-1'-ylpropyl)pyrrolidine-2-carboxamide
xref: CHEMBL201945
synonym: Banyu Compound-24
synonym: C-24
approved: f
ligand name: compound 24 [PMID: 16451050]
type: SyntheticOrganicLigand

trimethadione
canonical SMILES: O=C1OC(C(=O)N1C)(C)C
isomeric SMILES: O=C1OC(C(=O)N1C)(C)C
in ch i key: IRYJRGCIQBGHIV-UHFFFAOYSA-N
in ch i: InChI=1S/C6H9NO3/c1-6(2)4(8)7(3)5(9)10-6/h1-3H3
comment: Trimethadione is an anticonvulsant.
iupac name: trimethyl-1,3-oxazolidine-2,4-dione
xref: CHEMBL695
synonym: Tridione®
approved: t
ligand name: trimethadione
type: SyntheticOrganicLigand

AZD1283
in ch i key: NEMHKCNXXRQYRF-UHFFFAOYSA-N
in ch i: InChI=1S/C23H26N4O5S/c1-3-32-23(29)20-13-19(14-24)21(25-16(20)2)27-11-9-18(10-12-27)22(28)26-33(30,31)15-17-7-5-4-6-8-17/h4-8,13,18H,3,9-12,15H2,1-2H3,(H,26,28)
comment: Antagonist of P2Y12 developed as non-nucleoside analogue alternative to marketed inhibitors such as <Ligand id=1765/> <Reference id=24094/><Reference id=24093/>. An antiplatelet agent that is orally bioavailable and has improved drug-like properties was discovered through optimization of AZD1283 <Reference id=37457/>.
iupac name: ethyl 5-cyano-2-methyl-6-[4-(phenylmethylsulfonylcarbamoyl)piperidin-1-yl]pyridine-3-carboxylate
xref: CHEMBL2419490
synonym: AZD-1283
synonym: AZD 1283
approved: f
ligand name: AZD1283
type: SyntheticOrganicLigand

p-hydroxyatorvastatin
in ch i key: SOZOATLLFFVAPM-KAYWLYCHSA-N
in ch i: InChI=1S/C33H35FN2O6/c1-20(2)31-30(33(42)35-24-12-14-25(37)15-13-24)29(21-6-4-3-5-7-21)32(22-8-10-23(34)11-9-22)36(31)17-16-26(38)18-27(39)19-28(40)41/h3-15,20,26-27,37-39H,16-19H2,1-2H3,(H,35,42)(H,40,41)/t26-,27-/m1/s1
comment: One of the actve metabolites of the approved drug atorvastatin.
iupac name: (3R,5R)-7-[2-(4-fluorophenyl)-4-[(4-hydroxyphenyl)carbamoyl]-3-phenyl-5-propan-2-ylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid
approved: f
ligand name: p-hydroxyatorvastatin
type: SyntheticOrganicLigand

E2012
isomeric SMILES: COc1cc(ccc1n1cnc(c1)C)/C=C/1/CCCN(C1=O)[C@H](c1ccc(cc1)F)C
in ch i key: PUOAETJYKQITMO-LANLRWRYSA-N
in ch i: InChI=1S/C25H26FN3O2/c1-17-15-28(16-27-17)23-11-6-19(14-24(23)31-3)13-21-5-4-12-29(25(21)30)18(2)20-7-9-22(26)10-8-20/h6-11,13-16,18H,4-5,12H2,1-3H3/b21-13+/t18-/m0/s1
comment: E2012 is a gamma -secretase modulator that differentially reduces plasma Aβ40 and Abβ42 levels while sparing notch cleavage in healthy human subjects following single dose oral administration for the treatment of Alzheimer's disease. However, induced cataract following repeated doses in the rat may halt development <Reference id=24085/>.
iupac name: (3E)-1-[(1S)-1-(4-fluorophenyl)ethyl]-3-[[3-methoxy-4-(4-methylimidazol-1-yl)phenyl]methylidene]piperidin-2-one
xref: CHEMBL1224151
synonym: E 2012
synonym: E-2012
approved: f
ligand name: E2012
type: SyntheticOrganicLigand

ABT-384
in ch i key: CLHMYBJIOZXCEX-UHFFFAOYSA-N
in ch i: InChI=1S/C25H34F3N5O2/c1-23(2,33-7-5-32(6-8-33)19-4-3-18(14-30-19)25(26,27)28)22(35)31-20-16-9-15-10-17(20)13-24(11-15,12-16)21(29)34/h3-4,14-17,20H,5-13H2,1-2H3,(H2,29,34)(H,31,35)
comment: A range of medical conditions, including major depressive disorder and Alzheimer's disease, have been associated with excess levels of the stress hormone cortisol. ABT-384 is a potent and selective inhibitor of 11-beta-hydroxysteroid dehydrogenase type 1 (HSD-1) that generates cortisol. It has completed a phase 1 trial <Reference id=24080/> but failed a phase II trial for Alzheimer's disease <Reference id=24081/>. ChEMBL represents this compound with specified stereochemistry with the entry CHEMBL222670.
iupac name: 4-[[2-methyl-2-[4-[5-(trifluoromethyl)pyridin-2-yl]piperazin-1-yl]propanoyl]amino]adamantane-1-carboxamide
synonym: ABT384
synonym: ABT 384
approved: f
ligand name: ABT-384
type: SyntheticOrganicLigand

cerlapirdine
in ch i key: NXQGEDVQXVTCDA-UHFFFAOYSA-N
in ch i: InChI=1S/C22H23N3O3S/c1-25(2)13-6-14-28-17-11-12-20-19(15-17)22(24-23-20)29(26,27)21-10-5-8-16-7-3-4-9-18(16)21/h3-5,7-12,15H,6,13-14H2,1-2H3,(H,23,24)
comment: Cerlapirdine is a Wyeth/Pfizer selective 5-HT6 receptor antagonist for the treatment of cognitive disorders associated with Alzheimer's disease and schizophrenia <Reference id=22865/> . Since the phase 2 trial was stopped development may have ceased. Note, unusually, this INN is PubMed-negative so you will need to search the synonyms to find publications. The hydrochloride salt is CID 53385647.
iupac name: N,N-dimethyl-3-[(3-naphthalen-1-ylsulfonyl-2H-indazol-5-yl)oxy]propan-1-amine
xref: CHEMBL2103880
synonym: SAM-531
synonym: WAY-262531
synonym: PF-05212365
approved: f
ligand name: cerlapirdine
type: SyntheticOrganicLigand

bazedoxifene
in ch i key: UCJGJABZCDBEDK-UHFFFAOYSA-N
in ch i: InChI=1S/C30H34N2O3/c1-22-28-20-26(34)12-15-29(28)32(30(22)24-8-10-25(33)11-9-24)21-23-6-13-27(14-7-23)35-19-18-31-16-4-2-3-5-17-31/h6-15,20,33-34H,2-5,16-19,21H2,1H3
comment: Bazedoxifene is a selective estrogen receptor modulator (SERM).
iupac name: 1-[[4-[2-(azepan-1-yl)ethoxy]phenyl]methyl]-2-(4-hydroxyphenyl)-3-methylindol-5-ol
xref: CHEMBL46740
synonym: WAY-140424
synonym: Aprela
synonym: Duavee
synonym: TSE-424
synonym: Viviant®
synonym: Conbriza®
approved: t
ligand name: bazedoxifene
type: SyntheticOrganicLigand

umeclidinium
in ch i key: FVTWTVQXNAJTQP-UHFFFAOYSA-N
in ch i: InChI=1S/C29H34NO2/c31-29(26-12-6-2-7-13-26,27-14-8-3-9-15-27)28-16-19-30(20-17-28,21-18-28)22-23-32-24-25-10-4-1-5-11-25/h1-15,31H,16-24H2/q+1
comment: The compound approved in Anoro Ellipta® is umeclidinium bromide (PubChem CID 11519069), and this preparation is documented in the INN record. We display the parent compound here.
iupac name: di(phenyl)-[1-[2-(phenylmethoxy)ethyl]-1-azoniabicyclo[2.2.2]octan-4-yl]methanol
xref: CHEMBL1187833
synonym: GSK573719A
synonym: Incruse Ellipta®
approved: t
ligand name: umeclidinium
type: SyntheticOrganicLigand

vilanterol
in ch i key: DAFYYTQWSAWIGS-DEOSSOPVSA-N
in ch i: InChI=1S/C24H33Cl2NO5/c25-21-6-5-7-22(26)20(21)17-32-13-12-31-11-4-2-1-3-10-27-15-24(30)18-8-9-23(29)19(14-18)16-28/h5-9,14,24,27-30H,1-4,10-13,15-17H2/t24-/m0/s1
comment: Vilanterol is an ultra-long-acting β2-adrenoreceptor agonist, belonging to a group of drugs termed ultra-LABAs.
xref: CHEMBL1198857
synonym: GW642444X
approved: t
ligand name: vilanterol
type: SyntheticOrganicLigand

orciprenaline
canonical SMILES: OC(c1cc(O)cc(c1)O)CNC(C)C
isomeric SMILES: OC(c1cc(O)cc(c1)O)CNC(C)C
in ch i key: LMOINURANNBYCM-UHFFFAOYSA-N
in ch i: InChI=1S/C11H17NO3/c1-7(2)12-6-11(15)8-3-9(13)5-10(14)4-8/h3-5,7,11-15H,6H2,1-2H3
comment: Orciprenaline is a β-adrenoceptor agonist.
iupac name: 5-{1-hydroxy-2-[(propan-2-yl)amino]ethyl}benzene-1,3-diol
xref: CHEMBL776
synonym: Prometa
synonym: Alupent®
synonym: metaproterenol sulfate
synonym: TH-152
approved: t
ligand name: orciprenaline
type: SyntheticOrganicLigand

macitentan
in ch i key: JGCMEBMXRHSZKX-UHFFFAOYSA-N
comment: Macitentan is an endothelin receptor antagonist (ERA). It exhibits approximately 50-fold selectivity for the ETA receptor over the ETB receptor <Reference id=31249/>.
iupac name: 5-(4-bromophenyl)-6-[2-(5-bromopyrimidin-2-yl)oxyethoxy]-N-(propylsulfamoyl)pyrimidin-4-amine
xref: CHEMBL2103873
synonym: ACT-064992
synonym: Opsumit®
approved: t
ligand name: macitentan
type: SyntheticOrganicLigand

vortioxetine
canonical SMILES: Cc1ccc(c(c1)C)Sc1ccccc1N1CCNCC1
isomeric SMILES: Cc1ccc(c(c1)C)Sc1ccccc1N1CCNCC1
in ch i key: YQNWZWMKLDQSAC-UHFFFAOYSA-N
in ch i: InChI=1S/C18H22N2S/c1-14-7-8-17(15(2)13-14)21-18-6-4-3-5-16(18)20-11-9-19-10-12-20/h3-8,13,19H,9-12H2,1-2H3
comment: Vortioxetine is a novel atypical antidepressant.
xref: CHEMBL2104993
synonym: Trintellix®
synonym: Brintellix®
synonym: Lu AA21004
approved: t
ligand name: vortioxetine
type: SyntheticOrganicLigand

eslicarbazepine
canonical SMILES: OC1Cc2ccccc2N(c2c1cccc2)C(=O)N
isomeric SMILES: O[C@H]1Cc2ccccc2N(c2c1cccc2)C(=O)N
in ch i key: BMPDWHIDQYTSHX-AWEZNQCLSA-N
in ch i: InChI=1S/C15H14N2O2/c16-15(19)17-12-7-3-1-5-10(12)9-14(18)11-6-2-4-8-13(11)17/h1-8,14,18H,9H2,(H2,16,19)/t14-/m0/s1
comment: Eslicarbazepine is an anticonvulsant. The PubChem CID for eslicarbazepine acetate is CID 179344.
iupac name: (5S)-5-hydroxy-5,6-dihydrobenzo[b][1]benzazepine-11-carboxamide
xref: CHEMBL315985
synonym: Zebinix®
synonym: BIA 2-194
synonym: Erelib
synonym: Stedesa
synonym: S-licarbazepine
synonym: Exalief
synonym: Aptiom®
approved: t
ligand name: eslicarbazepine
type: SyntheticOrganicLigand

ospemifene
isomeric SMILES: ClCC/C(=C(/c1ccccc1)/c1ccc(cc1)OCCO)/c1ccccc1
in ch i key: LUMKNAVTFCDUIE-VHXPQNKSSA-N
in ch i: InChI=1S/C24H23ClO2/c25-16-15-23(19-7-3-1-4-8-19)24(20-9-5-2-6-10-20)21-11-13-22(14-12-21)27-18-17-26/h1-14,26H,15-18H2/b24-23-
comment: Ospemifene is a selective estrogen receptor modulator (SERM) <Reference id=24038/>.
iupac name: 2-[4-[(Z)-4-chloro-1,2-di(phenyl)but-1-enyl]phenoxy]ethanol
xref: CHEMBL2105395
synonym: Senshio®
synonym: FC-1271
synonym: Osphena®
approved: t
ligand name: ospemifene
type: SyntheticOrganicLigand

pomalidomide
in ch i key: UVSMNLNDYGZFPF-UHFFFAOYSA-N
in ch i: InChI=1S/C13H11N3O4/c14-7-3-1-2-6-10(7)13(20)16(12(6)19)8-4-5-9(17)15-11(8)18/h1-3,8H,4-5,14H2,(H,15,17,18)
comment: Pomalidomide is an analogue of thalidomide with similar immunomodulatory antineoplastic activity.
iupac name: 4-amino-2-(2,6-dioxopiperidin-3-yl)isoindole-1,3-dione
xref: CHEMBL43452
synonym: IMID-3
synonym: CC-4047
synonym: Actimid
synonym: Pomalyst®
synonym: Imnovid®
approved: t
ligand name: pomalidomide
type: SyntheticOrganicLigand

MK-0249
in ch i key: DDDZBLNULGDPGA-UHFFFAOYSA-N
in ch i: InChI=1S/C23H24F3N3O2/c1-16-27-20-7-4-6-19(23(24,25)26)21(20)22(30)29(16)17-8-10-18(11-9-17)31-15-5-14-28-12-2-3-13-28/h4,6-11H,2-3,5,12-15H2,1H3
comment: H3 receptor inverse agonists may be efficacious for central nervous system disorders, including excessive daytime sleepiness, attention deficit hyperactivity disorder, Alzheimer disease, ethanol addiction, and obesity <Reference id=23996/>.
iupac name: 2-methyl-3-[4-(3-pyrrolidin-1-ylpropoxy)phenyl]-5-(trifluoromethyl)quinazolin-4-one
xref: CHEMBL476323
synonym: MK0249
synonym: MK 0249
approved: f
ligand name: MK-0249
type: SyntheticOrganicLigand

florbetapir
canonical SMILES: FCCOCCOCCOc1ccc(cn1)C=Cc1ccc(cc1)NC
in ch i key: YNDIAUKFXKEXSV-CRYLGTRXSA-N
in ch i: InChI=1S/C20H25FN2O3/c1-22-19-7-4-17(5-8-19)2-3-18-6-9-20(23-16-18)26-15-14-25-13-12-24-11-10-21/h2-9,16,22H,10-15H2,1H3/b3-2+/i21-1
comment: Florbetapir F18 is a molecular imaging agent (diagnostic radiopharmaceutical) that binds to β-amyloid aggregates in Alzheimer's brains.
iupac name: 4-[(E)-2-[6-(2-{2-[2-(18F)fluoroethoxy]ethoxy}ethoxy)pyridin-3-yl]ethenyl]-N-methylaniline
xref: CHEMBL1774461
synonym: florbetapir (18F)
synonym: AV-45
synonym: AMYViD®
approved: t
ligand name: florbetapir
type: SyntheticOrganicLigand

flutemetamol
canonical SMILES: CNc1ccc(cc1F)c1nc2c(s1)cc(cc2)O
isomeric SMILES: CNc1ccc(cc1[18F])c1nc2c(s1)cc(cc2)O
in ch i key: VVECGOCJFKTUAX-HUYCHCPVSA-N
in ch i: InChI=1S/C14H11FN2OS/c1-16-11-4-2-8(6-10(11)15)14-17-12-5-3-9(18)7-13(12)19-14/h2-7,16,18H,1H3/i15-1
comment: Flutemetamol F-18 (Vizamyl GE Healthcare) is a positron emission tomography (PET) radiotracer approved in 2013 that binds to amyloid plaques in Alzheimer's disease neurodegeneration. However imaging agents have been granted only narrow approval since they can not be used to definitively diagnose Alzheimer's disease or to gauge treatment effectiveness, only to support other diagnostic criteria <Reference id=23972/>.
iupac name: 2-[3-(18F)fluoro-4-(methylamino)phenyl]-1,3-benzothiazol-6-ol
xref: CHEMBL2042122
synonym: flutemetamol F18
synonym: [18F]flutemetamol
synonym: 18F-flutemetamol
synonym: Vizamyl
approved: t
ligand name: flutemetamol
type: SyntheticOrganicLigand

RO4929097
in ch i key: OJPLJFIFUQPSJR-INIZCTEOSA-N
in ch i: InChI=1S/C22H20F5N3O3/c1-20(2,18(32)28-11-21(23,24)22(25,26)27)19(33)30-16-14-9-4-3-7-12(14)13-8-5-6-10-15(13)29-17(16)31/h3-10,16H,11H2,1-2H3,(H,28,32)(H,29,31)(H,30,33)/t16-/m0/s1
comment: RO4929097 as an inhibitor of γ-secretase, was originally developed for Alzheimer's disease but based on its ability to inhibit the NOTCH pathway it was investigated as a therapeutic strategy against melanoma and other tumours <Reference id=23957/>.
iupac name: 2,2-dimethyl-N-[(10S)-9-oxo-8-azatricyclo[9.4.0.02,7]pentadeca-1(15),2,4,6,11,13-hexaen-10-yl]-N'-(2,2,3,3,3-pentafluoropropyl)propanediamide
synonym: Ro4929097
synonym: RG-4733
synonym: RG4733
approved: f
ligand name: RO4929097
type: SyntheticOrganicLigand

ELND006
in ch i key: XODSHWXKSMPDRP-LJQANCHMSA-N
comment: ELND006 is a novel γ-secretase inhibitor by Elan Corporation that was in the clinic as a potential treatment for Alzheimer's disease (AD). The clinical trial was halted in October 2010 due to liver side effects that are thought to be unrelated to the mechanism of action <Reference id=23955/>
iupac name: (4R)-4-cyclopropyl-7,8-difluoro-5-[4-(trifluoromethyl)benzenesulfonyl]-1H,4H,5H-pyrazolo[4,3-c]quinoline
xref: CHEMBL2396778
approved: f
ligand name: ELND006
type: SyntheticOrganicLigand

etazolate
canonical SMILES: CCOC(=O)c1cnc2c(c1NN=C(C)C)cnn2CC
isomeric SMILES: CCOC(=O)c1cnc2c(c1NN=C(C)C)cnn2CC
in ch i key: OPQRBXUBWHDHPQ-UHFFFAOYSA-N
in ch i: InChI=1S/C14H19N5O2/c1-5-19-13-10(8-16-19)12(18-17-9(3)4)11(7-15-13)14(20)21-6-2/h7-8H,5-6H2,1-4H3,(H,15,18)
comment: Has anxiolytic effects as positive allosteric modulator of the GABAA receptor at the barbiturate binding site, as an adenosine antagonist of the A1 and A2 receptor subtypes and as a phosphodiesterase inhibitor selective for the PDE4 isoform. It is currently in clinical trials for the treatment of Alzheimer's disease with a possible MMOA of upregulating alpha-secretase activity.
iupac name: ethyl 1-ethyl-4-(2-propan-2-ylidenehydrazinyl)pyrazolo[4,5-e]pyridine-5-carboxylate
xref: CHEMBL356388
synonym: EHT-0202
synonym: SQ 20009
approved: f
ligand name: etazolate
type: SyntheticOrganicLigand

oliceridine
canonical SMILES: COc1ccsc1CNCCC1(CCOC2(C1)CCCC2)c1ccccn1
in ch i key: DMNOVGJWPASQDL-OAQYLSRUSA-N
in ch i: InChI=1S/C22H30N2O2S/c1-25-18-7-15-27-19(18)16-23-13-10-21(20-6-2-5-12-24-20)11-14-26-22(17-21)8-3-4-9-22/h2,5-7,12,15,23H,3-4,8-11,13-14,16-17H2,1H3/t21-/m1/s1
comment: Oliceridine (TRV130) is an opioid compound. It was developed to exhibit biased-signalling (specifically bias towards G protein signalling), with the aim of reducing the adverse effects associated with use of other opioid drugs <Reference id=23936/><Reference id=23934/>.
iupac name: [(3-methoxythiophen-2-yl)methyl]({2-[(9R)-9-(pyridin-2-yl)-6-oxaspiro[4.5]decan-9-yl]ethyl})amine
xref: CHEMBL2443262
synonym: Olinvyk®
synonym: TRV130
synonym: TRV130A
approved: t
ligand name: oliceridine
type: SyntheticOrganicLigand

barasertib
in ch i key: GBJVVSCPOBPEIT-UHFFFAOYSA-N
in ch i: InChI=1S/C26H31FN7O6P/c1-2-34(10-12-40-41(36,37)38)9-4-11-39-21-7-8-22-23(16-21)28-17-29-26(22)31-24-14-20(32-33-24)15-25(35)30-19-6-3-5-18(27)13-19/h3,5-8,13-14,16-17H,2,4,9-12,15H2,1H3,(H,30,35)(H2,36,37,38)(H2,28,29,31,32,33)
comment: Barasertib is a pro-drug. The phosphate group is rapidly converted to a hydroxyl group in vivo generating the active form which is a selective inhibitor of aurora kinase B.
iupac name: 2-[ethyl-[3-[4-[[5-[2-(3-fluoroanilino)-2-oxoethyl]-1H-pyrazol-3-yl]amino]quinazolin-7-yl]oxypropyl]amino]ethyl dihydrogen phosphate
xref: CHEMBL415049
synonym: AZD1152
approved: f
ligand name: barasertib
type: SyntheticOrganicLigand

lenalidomide
canonical SMILES: OC1=NC(=O)C(CC1)N1Cc2c(C1=O)cccc2N
isomeric SMILES: OC1=NC(=O)C(CC1)N1Cc2c(C1=O)cccc2N
in ch i key: GOTYRUGSSMKFNF-UHFFFAOYSA-N
in ch i: InChI=1S/C13H13N3O3/c14-9-3-1-2-7-8(9)6-16(13(7)19)10-4-5-11(17)15-12(10)18/h1-3,10H,4-6,14H2,(H,15,17,18)
comment: Lenalidomide is a derivative of <Ligand id=7327/> with anti-inflammatory and anti-cancer actions.
iupac name: 4-amino-2-(6-hydroxy-2-oxo-2,3,4,5-tetrahydropyridin-3-yl)-2,3-dihydro-1H-isoindol-1-one
xref: CHEMBL848
synonym: CC-5013
synonym: CDC-501
synonym: Revlimid®
approved: t
ligand name: lenalidomide
type: SyntheticOrganicLigand

metharbital
canonical SMILES: CCC1(CC)C(=NC(=O)N(C1=O)C)O
isomeric SMILES: CCC1(CC)C(=NC(=O)N(C1=O)C)O
in ch i key: FWJKNZONDWOGMI-UHFFFAOYSA-N
in ch i: InChI=1S/C9H14N2O3/c1-4-9(5-2)6(12)10-8(14)11(3)7(9)13/h4-5H2,1-3H3,(H,10,12,14)
comment: Metharbital is a barbiturate anticonvulsant.
iupac name: 5,5-diethyl-6-hydroxy-3-methyl-2,3,4,5-tetrahydropyrimidine-2,4-dione
xref: CHEMBL450
synonym: Gemonil®
approved: t
ligand name: metharbital
type: SyntheticOrganicLigand

dexrazoxane
canonical SMILES: OC1=NC(=O)CN(C1)CC(N1CC(=NC(=O)C1)O)C
in ch i key: BMKDZUISNHGIBY-ZETCQYMHSA-N
in ch i: InChI=1S/C11H16N4O4/c1-7(15-5-10(18)13-11(19)6-15)2-14-3-8(16)12-9(17)4-14/h7H,2-6H2,1H3,(H,12,16,17)(H,13,18,19)/t7-/m0/s1
comment: Dexrazoxane is an EDTA derivative with iron-chelating activity.
iupac name: 6-hydroxy-4-[(2S)-2-(5-hydroxy-3-oxo-1,2,3,6-tetrahydropyrazin-1-yl)propyl]-2,3,4,5-tetrahydropyrazin-2-one
xref: CHEMBL1738
synonym: Savene®
synonym: ADR-529
synonym: ICRF-187
synonym: Totect
synonym: Zinecard®
synonym: Cardioxane®
approved: t
ligand name: dexrazoxane
type: SyntheticOrganicLigand

pemirolast
canonical SMILES: Cc1cccn2c1ncc(c2=O)c1n[nH]nn1
isomeric SMILES: Cc1cccn2c1ncc(c2=O)c1n[nH]nn1
in ch i key: HIANJWSAHKJQTH-UHFFFAOYSA-N
in ch i: InChI=1S/C10H8N6O/c1-6-3-2-4-16-9(6)11-5-7(10(16)17)8-12-14-15-13-8/h2-5H,1H3,(H,12,13,14,15)
comment: Pemirolast is an antihistamine. Marketed formulations may contain pemirolast potassium salt (PubChem CID 443866).
iupac name: 9-methyl-3-(2H-1,2,3,4-tetrazol-5-yl)-4H-pyrido[1,2-a]pyrimidin-4-one
xref: CHEMBL1201198
synonym: Alamast®
synonym: BMY-26517
synonym: Alegysal®
approved: t
ligand name: pemirolast
type: SyntheticOrganicLigand

tromethamine
canonical SMILES: OCC(CO)(CO)N
isomeric SMILES: OCC(CO)(CO)N
in ch i key: LENZDBCJOHFCAS-UHFFFAOYSA-N
in ch i: InChI=1S/C4H11NO3/c5-4(1-6,2-7)3-8/h6-8H,1-3,5H2
comment: Tromethamine (commonly called tris) is used widely as a biochemical buffer, but is also an approved drug (in which case it is sometimes referred to as THAM)..
iupac name: 2-amino-2-(hydroxymethyl)propane-1,3-diol
xref: CHEMBL1200391
synonym: THAM
synonym: trometamol
synonym: tris
approved: t
ligand name: tromethamine
type: SyntheticOrganicLigand

thalidomide
canonical SMILES: OC1=NC(=O)C(CC1)N1C(=O)c2c(C1=O)cccc2
isomeric SMILES: OC1=NC(=O)C(CC1)N1C(=O)c2c(C1=O)cccc2
in ch i key: UEJJHQNACJXSKW-UHFFFAOYSA-N
in ch i: InChI=1S/C13H10N2O4/c16-10-6-5-9(11(17)14-10)15-12(18)7-3-1-2-4-8(7)13(15)19/h1-4,9H,5-6H2,(H,14,16,17)
comment: Thalidomide is principally an immunomodulatory drug. It inhibits synthesis of TNFα. Mechanistically, thalidomide binds to cereblon, and this complex recruits substrate proteins for degradation by the ubiquitin system. The lymphoid transcription factors Ikaros (IKZF1) and Aiolos (IKZF3) have been identified as substrates for thalidomide-bound cereblon. More recently another transcription factor, PLZF (ZBTB16), has been reported as a potential thalidomide/cereblon substrate <Reference id=38967/>. Knockdown of Plfz induces skeletal abnormalities in chicken limbs, so thalidomide-targeted degradation of PLZF would be predicted to exhibit similar teratogenic effects. SARS-CoV-2 and COVID-19: Thalidomide + low-dose glucocorticoid is being evaluated for efficacy in severe COVID-19 pneumonia (preprint available here https://www.preprints.org/manuscript/202002.0395/v1). An alternative approach is examining the combination of thalidomide + celecoxib (which targets NF-κB to suppress production of inflammatory cytokines; see preprint DOI: 10.13140/RG.2.2.26979.91689).
iupac name: 2-(6-hydroxy-2-oxo-2,3,4,5-tetrahydropyridin-3-yl)-2,3-dihydro-1H-isoindole-1,3-dione
xref: CHEMBL468
synonym: K-17
synonym: Thalomid
synonym: Immunoprin
synonym: Talidex
synonym: Talizer
synonym: Contergan
approved: t
ligand name: thalidomide
type: SyntheticOrganicLigand

hydralazine
canonical SMILES: NN=c1[nH]ncc2c1cccc2
isomeric SMILES: NN=c1[nH]ncc2c1cccc2
in ch i key: RPTUSVTUFVMDQK-UHFFFAOYSA-N
in ch i: InChI=1S/C8H8N4/c9-11-8-7-4-2-1-3-6(7)5-10-12-8/h1-5H,9H2,(H,11,12)
comment: Hydralazine is a hydrazinophthalazine class anti-hypertensiove drug. Hydralazine is on the World Health Organisation's List of Essential Medicines. Click here to access the pdf version of the WHO's 21st Essential Medicines list (2019).
iupac name: 1-hydrazinylidene-1,2-dihydrophthalazine
xref: CHEMBL276832
synonym: Dralzine
synonym: Apresoline®
approved: t
ligand name: hydralazine
type: SyntheticOrganicLigand

ethinamate
canonical SMILES: C#CC1(CCCCC1)OC(=N)O
isomeric SMILES: C#CC1(CCCCC1)OC(=N)O
in ch i key: GXRZIMHKGDIBEW-UHFFFAOYSA-N
in ch i: InChI=1S/C9H13NO2/c1-2-9(12-8(10)11)6-4-3-5-7-9/h1H,3-7H2,(H2,10,11)
comment: Ethinamate is a short-acting sedative-hypnotic type drug.
iupac name: [(1-ethynylcyclohexyl)oxy]methanimidic acid
xref: CHEMBL1576
synonym: Valmid®
approved: t
ligand name: ethinamate
type: SyntheticOrganicLigand

chlophedianol
canonical SMILES: CN(CCC(c1ccccc1Cl)(c1ccccc1)O)C
isomeric SMILES: CN(CCC(c1ccccc1Cl)(c1ccccc1)O)C
in ch i key: WRCHFMBCVFFYEQ-UHFFFAOYSA-N
in ch i: InChI=1S/C17H20ClNO/c1-19(2)13-12-17(20,14-8-4-3-5-9-14)15-10-6-7-11-16(15)18/h3-11,20H,12-13H2,1-2H3
comment: Chlophedianol is a centrally acting over-the-counter antitussive.
iupac name: 1-(2-chlorophenyl)-3-(dimethylamino)-1-phenylpropan-1-ol
xref: CHEMBL1201313
synonym: SL-501
synonym: ULO
synonym: Ulone®
approved: t
ligand name: chlophedianol
type: SyntheticOrganicLigand

chlormezanone
canonical SMILES: CN1C(=O)CCS(=O)(=O)C1c1ccc(cc1)Cl
isomeric SMILES: CN1C(=O)CCS(=O)(=O)C1c1ccc(cc1)Cl
in ch i key: WEQAYVWKMWHEJO-UHFFFAOYSA-N
in ch i: InChI=1S/C11H12ClNO3S/c1-13-10(14)6-7-17(15,16)11(13)8-2-4-9(12)5-3-8/h2-5,11H,6-7H2,1H3
comment: This is a non-benzodiazepine drug.
iupac name: 2-(4-chlorophenyl)-3-methyl-1,1-dioxo-1,3-thiazinan-4-one
xref: CHEMBL1200714
synonym: chlormethazanone
synonym: Trancopa®
synonym: Fenaprim®
approved: t
ligand name: chlormezanone
type: SyntheticOrganicLigand

venlafaxine
canonical SMILES: COc1ccc(cc1)C(C1(O)CCCCC1)CN(C)C
isomeric SMILES: COc1ccc(cc1)C(C1(O)CCCCC1)CN(C)C
in ch i key: PNVNVHUZROJLTJ-UHFFFAOYSA-N
in ch i: InChI=1S/C17H27NO2/c1-18(2)13-16(17(19)11-5-4-6-12-17)14-7-9-15(20-3)10-8-14/h7-10,16,19H,4-6,11-13H2,1-3H3
comment: Venlafaxine is a selective serotonin-norepinephrine reuptake inhibitor (SNRI); a bicyclic antidepressant. Venlafaxine is a racemic mixture of R (PubChem CID 9795623) and S (PubChem CID 11846746) stereoisomers, which have assay data in PubChem but its is unclear if these apply to the experimentally separated forms. Marketed formulations may contain venlafaxine hydrochloride (PubChem CID 62923). The major active metabolite of venlafaxine, <Ligand id=7158/> (O-desmethylvenlafaxine) has also been developed as a drug.
iupac name: 1-[2-(dimethylamino)-1-(4-methoxyphenyl)ethyl]cyclohexan-1-ol
xref: CHEMBL637
synonym: Effexor Xr
synonym: Effexor®
synonym: WY-45030
approved: t
ligand name: venlafaxine
type: SyntheticOrganicLigand

vardenafil
in ch i key: SECKRCOLJRRGGV-UHFFFAOYSA-N
in ch i: InChI=1S/C23H32N6O4S/c1-5-8-20-24-16(4)21-23(30)25-22(26-29(20)21)18-15-17(9-10-19(18)33-7-3)34(31,32)28-13-11-27(6-2)12-14-28/h9-10,15H,5-8,11-14H2,1-4H3,(H,25,26,30)
comment: Vardenafil is a phosphodiesterase type 5 (PDE5A) inhibitor. Marketed formulations may contain vardenafil hydrochloride (PubChem CID 10142962).
iupac name: 2-{2-ethoxy-5-[(4-ethylpiperazin-1-yl)sulfonyl]phenyl}-5-methyl-7-propyl-1H,4H-imidazo[4,3-f][1,2,4]triazin-4-one
xref: CHEMBL1520
synonym: Staxyn
synonym: Levitra®
synonym: Vivanza®
approved: t
ligand name: vardenafil
type: SyntheticOrganicLigand

tropicamide
canonical SMILES: CCN(C(=O)C(c1ccccc1)CO)Cc1ccncc1
isomeric SMILES: CCN(C(=O)C(c1ccccc1)CO)Cc1ccncc1
in ch i key: BGDKAVGWHJFAGW-UHFFFAOYSA-N
in ch i: InChI=1S/C17H20N2O2/c1-2-19(12-14-8-10-18-11-9-14)17(21)16(13-20)15-6-4-3-5-7-15/h3-11,16,20H,2,12-13H2,1H3
comment: Tropicamide is an antimuscarinic drug.
iupac name: N-ethyl-3-hydroxy-2-phenyl-N-(pyridin-4-ylmethyl)propanamide
xref: CHEMBL1200604
synonym: Mydriafair
synonym: Tropicacyl
synonym: Mydriacyl®
approved: t
ligand name: tropicamide
type: SyntheticOrganicLigand

tripelennamine
canonical SMILES: CN(CCN(c1ccccn1)Cc1ccccc1)C
isomeric SMILES: CN(CCN(c1ccccn1)Cc1ccccc1)C
in ch i key: UFLGIAIHIAPJJC-UHFFFAOYSA-N
in ch i: InChI=1S/C16H21N3/c1-18(2)12-13-19(16-10-6-7-11-17-16)14-15-8-4-3-5-9-15/h3-11H,12-14H2,1-2H3
comment: Tripelennamine is a first-generation antihistamine. It also has serotonin reuptake inhibitor (SRI) activity, and was used as the template molecule in the development of the selective serotonin reuptake inhibitor (SSRI) <Ligand id=7189/>. In addition, tripelennamine has dopamine reuptake inhibitor (DRI) activity.
iupac name: N-benzyl-N-[2-(dimethylamino)ethyl]pyridin-2-amine
xref: CHEMBL1241
synonym: PBZ
synonym: Pbz-Sr
synonym: Pyribenzamine®
approved: t
ligand name: tripelennamine
type: SyntheticOrganicLigand

trimipramine
canonical SMILES: CN(CC(CN1c2ccccc2CCc2c1cccc2)C)C
isomeric SMILES: CN(CC(CN1c2ccccc2CCc2c1cccc2)C)C
in ch i key: ZSCDBOWYZJWBIY-UHFFFAOYSA-N
in ch i: InChI=1S/C20H26N2/c1-16(14-21(2)3)15-22-19-10-6-4-8-17(19)12-13-18-9-5-7-11-20(18)22/h4-11,16H,12-15H2,1-3H3
comment: Trimipramine is a tricyclic antidepressant (TCA) with antidepressant, anxiolytic, antipsychotic and sedative effects. Trimipramine is a racemic compound of two enantiomers; (S)-trimipramine and (R)-trimipramine. We show the non-stereo structure to represent the mixture. Marketed formulations may contain trimipramine maleate (PubChem CID 5282318).
iupac name: 3-(5,6-dihydrobenzo[b][1]benzazepin-11-yl)-N,N,2-trimethylpropan-1-amine
xref: CHEMBL644
synonym: 7162 RP
synonym: IL-6001
synonym: Stangyl
synonym: Rhotrimine
synonym: Surmontil®
approved: t
ligand name: trimipramine
type: SyntheticOrganicLigand

torsemide
in ch i key: NGBFQHCMQULJNZ-UHFFFAOYSA-N
in ch i: InChI=1S/C16H20N4O3S/c1-11(2)18-16(21)20-24(22,23)15-10-17-8-7-14(15)19-13-6-4-5-12(3)9-13/h4-11H,1-3H3,(H,17,19)(H2,18,20,21)
comment: Torsemide is a loop diuretic.
iupac name: N-({4-[(3-methylphenyl)imino]-1,4-dihydropyridin-3-yl}sulfonyl)propane-2-carbamimidic acid
xref: CHEMBL1148
synonym: BM-02015
synonym: AC-4464
synonym: AC4464
synonym: Demadex®
synonym: Diuver
synonym: Examide
synonym: Soaanz®
approved: t
ligand name: torsemide
type: SyntheticOrganicLigand

tolmetin
canonical SMILES: OC(=O)Cc1ccc(n1C)C(=O)c1ccc(cc1)C
isomeric SMILES: OC(=O)Cc1ccc(n1C)C(=O)c1ccc(cc1)C
in ch i key: UPSPUYADGBWSHF-UHFFFAOYSA-N
in ch i: InChI=1S/C15H15NO3/c1-10-3-5-11(6-4-10)15(19)13-8-7-12(16(13)2)9-14(17)18/h3-8H,9H2,1-2H3,(H,17,18)
comment: Tolmetin is a nonsteroidal anti-inflammatory drug (NSAID) with analgesic and antipyretic activity. Marketed formulations may contain tolmetin sodium (PubChem CID 23665411).
iupac name: 2-[1-methyl-5-(4-methylbenzoyl)-1H-pyrrol-2-yl]acetic acid
xref: CHEMBL1020
synonym: McN-2559-21-98
synonym: MCN-2559
synonym: Tolectin DS
synonym: Tolectin 600
synonym: Tolectin®
approved: t
ligand name: tolmetin
type: SyntheticOrganicLigand

tolazoline
canonical SMILES: c1ccc(cc1)CC1=NCCN1
isomeric SMILES: c1ccc(cc1)CC1=NCCN1
in ch i key: JIVZKJJQOZQXQB-UHFFFAOYSA-N
in ch i: InChI=1S/C10H12N2/c1-2-4-9(5-3-1)8-10-11-6-7-12-10/h1-5H,6-8H2,(H,11,12)
comment: Tolazoline is a non-selective α-adrenoceptor antagonist.
iupac name: 2-benzyl-4,5-dihydro-1H-imidazole
xref: CHEMBL770
synonym: Priscol
synonym: Benzidazol
synonym: Priscoline
synonym: TCMDC-125842
approved: t
ligand name: tolazoline
type: SyntheticOrganicLigand

tocainide
canonical SMILES: CC(C(=Nc1c(C)cccc1C)O)N
isomeric SMILES: CC(C(=Nc1c(C)cccc1C)O)N
in ch i key: BUJAGSGYPOAWEI-UHFFFAOYSA-N
in ch i: InChI=1S/C11H16N2O/c1-7-5-4-6-8(2)10(7)13-11(14)9(3)12/h4-6,9H,12H2,1-3H3,(H,13,14)
comment: Tocainide is a lidocaine analog.
iupac name: 2-amino-N-(2,6-dimethylphenyl)propanimidic acid
xref: CHEMBL1762
synonym: Tonocard®
synonym: W-36095
approved: t
ligand name: tocainide
type: SyntheticOrganicLigand

tizanidine
canonical SMILES: Clc1ccc2c(c1NC1=NCCN1)nsn2
isomeric SMILES: Clc1ccc2c(c1NC1=NCCN1)nsn2
in ch i key: XFYDIVBRZNQMJC-UHFFFAOYSA-N
in ch i: InChI=1S/C9H8ClN5S/c10-5-1-2-6-8(15-16-14-6)7(5)13-9-11-3-4-12-9/h1-2H,3-4H2,(H2,11,12,13)
comment: Tizanidine is a centrally acting α2-adrenoceptor agonist. Marketed formulations may contain tizanidine hydrochloride (PubChem CID 114869).
iupac name: 5-chloro-N-(4,5-dihydro-1H-imidazol-2-yl)-2,1,3-benzothiadiazol-4-amine
xref: CHEMBL1079
synonym: DS-103-282
synonym: AN-021
synonym: Zanaflex®
approved: t
ligand name: tizanidine
type: SyntheticOrganicLigand

ticlopidine
canonical SMILES: Clc1ccccc1CN1CCc2c(C1)ccs2
isomeric SMILES: Clc1ccccc1CN1CCc2c(C1)ccs2
in ch i key: PHWBOXQYWZNQIN-UHFFFAOYSA-N
in ch i: InChI=1S/C14H14ClNS/c15-13-4-2-1-3-11(13)9-16-7-5-14-12(10-16)6-8-17-14/h1-4,6,8H,5,7,9-10H2
comment: Ticlopidine is an antiplatelet drug. This compound is believed to be a prodrug, although the exact form of the active metabolite remains elusive.
iupac name: 5-[(2-chlorophenyl)methyl]-4H,5H,6H,7H-thieno[3,2-c]pyridine
xref: CHEMBL833
synonym: 4-C-32
synonym: 53-32C
synonym: Ticlid®
approved: t
ligand name: ticlopidine
type: SyntheticOrganicLigand

thiethylperazine
in ch i key: XCTYLCDETUVOIP-UHFFFAOYSA-N
in ch i: InChI=1S/C22H29N3S2/c1-3-26-18-9-10-22-20(17-18)25(19-7-4-5-8-21(19)27-22)12-6-11-24-15-13-23(2)14-16-24/h4-5,7-10,17H,3,6,11-16H2,1-2H3
comment: Thiethylperazine is a phenothiazine class antiemetic. Experiments in a mouse model suggest it may have potential to clear amyloid-β (Aβ) load in Alzheimer's disease <Reference id=24011/>.
iupac name: 2-(ethylsulfanyl)-10-[3-(4-methylpiperazin-1-yl)propyl]-10H-phenothiazine
xref: CHEMBL1378
synonym: GS-95
synonym: Torecan®
approved: t
ligand name: thiethylperazine
type: SyntheticOrganicLigand

thiamylal
canonical SMILES: CCCC(C1(CC=C)C(=NC(=S)N=C1O)O)C
isomeric SMILES: CCCC(C1(CC=C)C(=NC(=S)N=C1O)O)C
in ch i key: XLOMZPUITCYLMJ-UHFFFAOYSA-N
in ch i: InChI=1S/C12H18N2O2S/c1-4-6-8(3)12(7-5-2)9(15)13-11(17)14-10(12)16/h5,8H,2,4,6-7H2,1,3H3,(H2,13,14,15,16,17)
comment: Thiamylal is a barbiturate with sedative, anticonvulsant and hypnotic effects.
iupac name: 4,6-dihydroxy-5-(pentan-2-yl)-5-(prop-2-en-1-yl)-2,5-dihydropyrimidine-2-thione
xref: CHEMBL440
synonym: Biotal
synonym: Anestatal
synonym: Thioseconal
synonym: Surital®
approved: t
ligand name: thiamylal
type: SyntheticOrganicLigand

thiabendazole
canonical SMILES: c1scc(n1)c1nc2c([nH]1)cccc2
isomeric SMILES: c1scc(n1)c1nc2c([nH]1)cccc2
in ch i key: WJCNZQLZVWNLKY-UHFFFAOYSA-N
in ch i: InChI=1S/C10H7N3S/c1-2-4-8-7(3-1)12-10(13-8)9-5-14-6-11-9/h1-6H,(H,12,13)
comment: Tiabendazole is a fungicide and parasiticide with potential anti-angiogenic (or vascular disrupting) action <Reference id=24010/>.
iupac name: 2-(1,3-thiazol-4-yl)-1H-1,3-benzodiazole
xref: CHEMBL625
synonym: MK-360
synonym: E233
synonym: TBZ
synonym: Equizole
synonym: Mintezol
synonym: Omnizole
approved: t
ligand name: thiabendazole
type: SyntheticOrganicLigand

testolactone
in ch i key: BPEWUONYVDABNZ-DZBHQSCQSA-N
in ch i: InChI=1S/C19H24O3/c1-18-9-7-13(20)11-12(18)3-4-14-15(18)8-10-19(2)16(14)5-6-17(21)22-19/h7,9,11,14-16H,3-6,8,10H2,1-2H3/t14-,15+,16+,18+,19+/m1/s1
comment: Testolactone is a progestin.
iupac name: (4aS,4bR,10aR,10bS,12aS)-10a,12a-dimethyl-4,4a,4b,5,6,10b,11,12-octahydro-3H-naphtho[2,1-f]chromene-2,8-dione
xref: CHEMBL1571
synonym: SQ-9538
synonym: Teslac®
approved: t
ligand name: testolactone
type: SyntheticOrganicLigand

terazosin
in ch i key: VCKUSRYTPJJLNI-UHFFFAOYSA-N
in ch i: InChI=1S/C19H25N5O4/c1-26-15-10-12-13(11-16(15)27-2)21-19(22-17(12)20)24-7-5-23(6-8-24)18(25)14-4-3-9-28-14/h10-11,14H,3-9H2,1-2H3,(H2,20,21,22)
comment: Postsynaptic α1-adrenoceptor inhibitor. Marketed formulations may contain terazosin hydrochloride (PubChem CID 44383).
iupac name: 6,7-dimethoxy-2-[4-(oxolane-2-carbonyl)piperazin-1-yl]-3,4-dihydroquinazolin-4-imine
xref: CHEMBL611
synonym: ABBOTT-45975
synonym: Hytrin®
approved: t
ligand name: terazosin
type: SyntheticOrganicLigand

temozolomide
canonical SMILES: NC(=O)c1ncn2c1nnn(c2=O)C
isomeric SMILES: NC(=O)c1ncn2c1nnn(c2=O)C
in ch i key: BPEGJWRSRHCHSN-UHFFFAOYSA-N
in ch i: InChI=1S/C6H6N6O2/c1-11-6(14)12-2-8-3(4(7)13)5(12)9-10-11/h2H,1H3,(H2,7,13)
comment: Temozolomide is a DNA alkylating agent.
iupac name: 3-methyl-4-oxo-3H,4H-imidazo[4,3-d][1,2,3,5]tetrazine-8-carboxamide
xref: CHEMBL810
synonym: CCRG-81045
synonym: M-39831
synonym: Temodar®
synonym: Temodal®
synonym: Temcad
synonym: Temomedac
approved: t
ligand name: temozolomide
type: SyntheticOrganicLigand

tadalafil
in ch i key: WOXKDUGGOYFFRN-IIBYNOLFSA-N
in ch i: InChI=1S/C22H19N3O4/c1-24-10-19(26)25-16(22(24)27)9-14-13-4-2-3-5-15(13)23-20(14)21(25)12-6-7-17-18(8-12)29-11-28-17/h2-8,16,21,23H,9-11H2,1H3/t16-,21-/m1/s1
comment: Tadafil is a phosphodiesterase type 5 (PDE5) inhibitor.
xref: CHEMBL779
synonym: IC351
synonym: Cialis®
synonym: Adcirca®
synonym: IC-351
approved: t
ligand name: tadalafil
type: SyntheticOrganicLigand

suprofen
canonical SMILES: OC(=O)C(c1ccc(cc1)C(=O)c1cccs1)C
isomeric SMILES: OC(=O)C(c1ccc(cc1)C(=O)c1cccs1)C
in ch i key: MDKGKXOCJGEUJW-UHFFFAOYSA-N
in ch i: InChI=1S/C14H12O3S/c1-9(14(16)17)10-4-6-11(7-5-10)13(15)12-3-2-8-18-12/h2-9H,1H3,(H,16,17)
comment: Suprofen is a nonsteroidal anti-inflammatory drug (NSAID) with analgesic and antipyretic activity.
iupac name: 2-[4-(thiophene-2-carbonyl)phenyl]propanoic acid
xref: CHEMBL956
synonym: R-25061
synonym: Profenal®
approved: t
ligand name: suprofen
type: SyntheticOrganicLigand

sotalol
canonical SMILES: CC(NCC(c1ccc(cc1)NS(=O)(=O)C)O)C
isomeric SMILES: CC(NCC(c1ccc(cc1)NS(=O)(=O)C)O)C
in ch i key: ZBMZVLHSJCTVON-UHFFFAOYSA-N
in ch i: InChI=1S/C12H20N2O3S/c1-9(2)13-8-12(15)10-4-6-11(7-5-10)14-18(3,16)17/h4-7,9,12-15H,8H2,1-3H3
comment: Sotalol is a β-blocker & potassium channel blocker. Marketed formulations may contain sotalol hydrochloride (PubChem CID 66245).
xref: CHEMBL471
synonym: MJ-1999
synonym: Sorine
synonym: Betapace Af
synonym: Betapace®
approved: t
ligand name: sotalol
type: SyntheticOrganicLigand

sevoflurane
canonical SMILES: FCOC(C(F)(F)F)C(F)(F)F
isomeric SMILES: FCOC(C(F)(F)F)C(F)(F)F
in ch i key: DFEYYRMXOJXZRJ-UHFFFAOYSA-N
in ch i: InChI=1S/C4H3F7O/c5-1-12-2(3(6,7)8)4(9,10)11/h2H,1H2
comment: Sevoflurane is a highly fluorinated methyl isopropyl ether inhalational anaesthetic, and it is one of the most commonly used inhalational anaesthetics. After <Ligand id=7156/>, it is the volatile anaesthetic with the fastest onset and offset <Reference id=31247/>.
iupac name: 1,1,1,3,3,3-hexafluoro-2-(fluoromethoxy)propane
xref: CHEMBL1200694
synonym: MR-6S4
synonym: MR6S4
synonym: Ultane®
synonym: Sojourn®
synonym: Sevorane
approved: t
ligand name: sevoflurane
type: SyntheticOrganicLigand

ropinirole
canonical SMILES: CCCN(CCC)CCc1cccc2c1CC(=N2)O
isomeric SMILES: CCCN(CCC)CCc1cccc2c1CC(=N2)O
in ch i key: UHSKFQJFRQCDBE-UHFFFAOYSA-N
in ch i: InChI=1S/C16H24N2O/c1-3-9-18(10-4-2)11-8-13-6-5-7-15-14(13)12-16(19)17-15/h5-7H,3-4,8-12H2,1-2H3,(H,17,19)
comment: Ropinirole is a dopamine agonist. This drug is active at the dopamine-D2 and -D3 receptor subtypes, both centrally and peripherally.
iupac name: 4-[2-(dipropylamino)ethyl]-3H-indol-2-ol
xref: CHEMBL589
synonym: Requip Xl
synonym: Ropinirole Hydrochloride
synonym: Requip®
synonym: SK&F-101468-A
synonym: SK&F-101468A
synonym: Adartrel
approved: t
ligand name: ropinirole
type: SyntheticOrganicLigand

ritodrine
canonical SMILES: Oc1ccc(cc1)CCNC(C(c1ccc(cc1)O)O)C
in ch i key: IOVGROKTTNBUGK-SJCJKPOMSA-N
in ch i: InChI=1S/C17H21NO3/c1-12(17(21)14-4-8-16(20)9-5-14)18-11-10-13-2-6-15(19)7-3-13/h2-9,12,17-21H,10-11H2,1H3/t12-,17-/m0/s1
comment: Ritodrine is a tocolytic drug (ie an anti-contraction medication). Clinical use in the US has been discontinued. Marketed formulations may contain ritodrine hydrochloride (PubChem CID 31728).
iupac name: 4-(2-{[(1R,2S)-1-hydroxy-1-(4-hydroxyphenyl)propan-2-yl]amino}ethyl)phenol
xref: CHEMBL785
synonym: DU-21220
synonym: Yutopar®
approved: t
ligand name: ritodrine
type: SyntheticOrganicLigand

remifentanil
in ch i key: ZTVQQQVZCWLTDF-UHFFFAOYSA-N
in ch i: InChI=1S/C20H28N2O5/c1-4-17(23)22(16-8-6-5-7-9-16)20(19(25)27-3)11-14-21(15-12-20)13-10-18(24)26-2/h5-9H,4,10-15H2,1-3H3
comment: Remifentanil is a synthetic opioid analgesic drug.
iupac name: methyl 1-(3-methoxy-3-oxopropyl)-4-(N-phenylpropanamido)piperidine-4-carboxylate
xref: CHEMBL1005
synonym: GI-87084B
synonym: Ultiva®
approved: t
ligand name: remifentanil
type: SyntheticOrganicLigand

ranolazine
in ch i key: XKLMZUWKNUAPSZ-UHFFFAOYSA-N
in ch i: InChI=1S/C24H33N3O4/c1-18-7-6-8-19(2)24(18)25-23(29)16-27-13-11-26(12-14-27)15-20(28)17-31-22-10-5-4-9-21(22)30-3/h4-10,20,28H,11-17H2,1-3H3,(H,25,29)
comment: The mechanism of action of ranolazine is largely unknown, but may have some antianginal effects by inhibition of the late sodium current in cardiac cells.
iupac name: N-(2,6-dimethylphenyl)-2-{4-[2-hydroxy-3-(2-methoxyphenoxy)propyl]piperazin-1-yl}ethanimidic acid
xref: CHEMBL1404
synonym: RS-43285-003
synonym: CVT-303
synonym: RS-43285
synonym: Ranexa®
approved: t
ligand name: ranolazine
type: SyntheticOrganicLigand

rabeprazole
in ch i key: YREYEVIYCVEVJK-UHFFFAOYSA-N
in ch i: InChI=1S/C18H21N3O3S/c1-13-16(19-9-8-17(13)24-11-5-10-23-2)12-25(22)18-20-14-6-3-4-7-15(14)21-18/h3-4,6-9H,5,10-12H2,1-2H3,(H,20,21)
comment: Rabeprazole is a proton pump inhibitor. This compound is a prodrug which is converted into the active sulphenamide form in the acid environment of the parietal cells. Marketed formulations may contain rabeprazole sodium (PubChem CID 14720269).
iupac name: 2-{[4-(3-methoxypropoxy)-3-methylpyridin-2-yl]methanesulfinyl}-1H-1,3-benzodiazole
xref: CHEMBL1219
synonym: AcipHex®
synonym: E-3810
synonym: Pariet®
approved: t
ligand name: rabeprazole
type: SyntheticOrganicLigand

quinethazone
canonical SMILES: CCC1Nc2cc(Cl)c(cc2C(=N1)O)S(=O)(=O)N
isomeric SMILES: CCC1Nc2cc(Cl)c(cc2C(=N1)O)S(=O)(=O)N
in ch i key: AGMMTXLNIQSRCG-UHFFFAOYSA-N
comment: Quinethazone is a diuretic.
iupac name: 7-chloro-2-ethyl-4-hydroxy-1,2-dihydroquinazoline-6-sulfonamide
xref: CHEMBL1532
synonym: Hydromox®
approved: t
ligand name: quinethazone
type: SyntheticOrganicLigand

pyrazinamide
canonical SMILES: OC(=N)c1cnccn1
isomeric SMILES: OC(=N)c1cnccn1
in ch i key: IPEHBUMCGVEMRF-UHFFFAOYSA-N
in ch i: InChI=1S/C5H5N3O/c6-5(9)4-3-7-1-2-8-4/h1-3H,(H2,6,9)
comment: This drug is often contained in fixed-mixture formulations with other antibacterial drugs beneficial in the treatment of TB (eg isoniazid and <Ligand id=2765/>).
iupac name: pyrazine-2-carboximidic acid
xref: CHEMBL614
synonym: Zinamide®
approved: t
ligand name: pyrazinamide
type: SyntheticOrganicLigand

pseudoephedrine
canonical SMILES: CNC(C(c1ccccc1)O)C
isomeric SMILES: CN[C@H]([C@H](c1ccccc1)O)C
in ch i key: KWGRBVOPPLSCSI-WCBMZHEXSA-N
in ch i: InChI=1S/C10H15NO/c1-8(11-2)10(12)9-6-4-3-5-7-9/h3-8,10-12H,1-2H3/t8-,10+/m0/s1
comment: Pseudoephedrine is a decongestant, often contained as one of the active ingredients in fixed-mixture cold and flu medications.
iupac name: (1S,2S)-2-(methylamino)-1-phenylpropan-1-ol
xref: CHEMBL1590
synonym: Afrinol
synonym: Novafed
synonym: Pseudophed
synonym: Sudafed 12 Hour
synonym: Sudafed 24 Hour
synonym: Sudafed®
synonym: pseudoephedrine hydrochloride
synonym: Sinutab®
synonym: pseudophedrine sulphate
approved: t
ligand name: pseudoephedrine
type: SyntheticOrganicLigand

protriptyline
canonical SMILES: CNCCCC1c2ccccc2C=Cc2c1cccc2
isomeric SMILES: CNCCCC1c2ccccc2C=Cc2c1cccc2
in ch i key: BWPIARFWQZKAIA-UHFFFAOYSA-N
in ch i: InChI=1S/C19H21N/c1-20-14-6-11-19-17-9-4-2-7-15(17)12-13-16-8-3-5-10-18(16)19/h2-5,7-10,12-13,19-20H,6,11,14H2,1H3
comment: Protriptyline is a tricyclic antidepressant. Marketed formulations may contain protriptyline hydrochloride (PubChem CID 6603149).
iupac name: 3-(11H-dibenzo[1,2-a:1',2'-e][7]annulen-11-yl)-N-methylpropan-1-amine
xref: CHEMBL668
synonym: MK-240
synonym: Vivactil®
approved: t
ligand name: protriptyline
type: SyntheticOrganicLigand

propiomazine
in ch i key: UVOIBTBFPOZKGP-UHFFFAOYSA-N
in ch i: InChI=1S/C20H24N2OS/c1-5-18(23)15-10-11-20-17(12-15)22(13-14(2)21(3)4)16-8-6-7-9-19(16)24-20/h6-12,14H,5,13H2,1-4H3
comment: Propiomazine is an antipsychotic drug. Marketed formulations may contain propiomazine hydrochloride (PubChem CID 71802).
iupac name: 1-{10-[2-(dimethylamino)propyl]-10H-phenothiazin-2-yl}propan-1-one
xref: CHEMBL1201210
synonym: CB-1678
synonym: WY-1359
synonym: Largon®
approved: t
ligand name: propiomazine
type: SyntheticOrganicLigand

proparacaine
canonical SMILES: CCCOc1ccc(cc1N)C(=O)OCCN(CC)CC
isomeric SMILES: CCCOc1ccc(cc1N)C(=O)OCCN(CC)CC
in ch i key: KCLANYCVBBTKTO-UHFFFAOYSA-N
in ch i: InChI=1S/C16H26N2O3/c1-4-10-20-15-8-7-13(12-14(15)17)16(19)21-11-9-18(5-2)6-3/h7-8,12H,4-6,9-11,17H2,1-3H3
comment: Proparacaine is a topical anesthetic drug.
iupac name: 2-(diethylamino)ethyl 3-amino-4-propoxybenzoate
xref: CHEMBL1196
synonym: Kainair
synonym: Ophthaine
synonym: Ophthetic
synonym: Alcaine®
synonym: proparacaine hydrochloride
synonym: Paracaine®
synonym: proxymetacaine hydrochloride
approved: t
ligand name: proparacaine
type: SyntheticOrganicLigand

promethazine
canonical SMILES: CN(C(CN1c2ccccc2Sc2c1cccc2)C)C
isomeric SMILES: CN(C(CN1c2ccccc2Sc2c1cccc2)C)C
in ch i key: PWWVAXIEGOYWEE-UHFFFAOYSA-N
in ch i: InChI=1S/C17H20N2S/c1-13(18(2)3)12-19-14-8-4-6-10-16(14)20-17-11-7-5-9-15(17)19/h4-11,13H,12H2,1-3H3
comment: This drug is a first-generation antihistamine with strong sedative and weak antipsychotic effects. Additional properties include antiemetic and anticholinergic actions.
iupac name: dimethyl[1-(10H-phenothiazin-10-yl)propan-2-yl]amine
xref: CHEMBL643
synonym: Remsed
synonym: Anergan
synonym: Zipan-25
synonym: Zipan-50
synonym: Protazine
synonym: Promethacon
synonym: Promethegan
synonym: Promethazine
synonym: Prometh Plain
synonym: Prometh Fortis
synonym: Mymethazine Fortis
synonym: Promethazine Plain
synonym: Phenergan®
synonym: Sominex®
approved: t
ligand name: promethazine
type: SyntheticOrganicLigand

promazine
canonical SMILES: CN(CCCN1c2ccccc2Sc2c1cccc2)C
isomeric SMILES: CN(CCCN1c2ccccc2Sc2c1cccc2)C
in ch i key: ZGUGWUXLJSTTMA-UHFFFAOYSA-N
in ch i: InChI=1S/C17H20N2S/c1-18(2)12-7-13-19-14-8-3-5-10-16(14)20-17-11-6-4-9-15(17)19/h3-6,8-11H,7,12-13H2,1-2H3
comment: Promazine is a phenothiazine antipsychotic. It is generally prescribed alongside newer antipsychotics such as <Ligand id=47/> and <Ligand id=50/>.
iupac name: dimethyl[3-(10H-phenothiazin-10-yl)propyl]amine
xref: CHEMBL564
synonym: Verophene
synonym: Tranquazine
synonym: Promazine Granules
synonym: Promazine Hydrochloride
synonym: Sparine®
approved: t
ligand name: promazine
type: SyntheticOrganicLigand

procyclidine
canonical SMILES: OC(c1ccccc1)(C1CCCCC1)CCN1CCCC1
isomeric SMILES: OC(c1ccccc1)(C1CCCCC1)CCN1CCCC1
in ch i key: WYDUSKDSKCASEF-UHFFFAOYSA-N
in ch i: InChI=1S/C19H29NO/c21-19(17-9-3-1-4-10-17,18-11-5-2-6-12-18)13-16-20-14-7-8-15-20/h1,3-4,9-10,18,21H,2,5-8,11-16H2
comment: Procyclidine is an anticholinergic drug.
iupac name: 1-cyclohexyl-1-phenyl-3-(pyrrolidin-1-yl)propan-1-ol
xref: CHEMBL86715
synonym: Kemadrin®
synonym: procyclidine hydrochloride
synonym: Arpicolin®
approved: t
ligand name: procyclidine
type: SyntheticOrganicLigand

prochlorperazine
canonical SMILES: CN1CCN(CC1)CCCN1c2ccccc2Sc2c1cc(Cl)cc2
isomeric SMILES: CN1CCN(CC1)CCCN1c2ccccc2Sc2c1cc(Cl)cc2
in ch i key: WIKYUJGCLQQFNW-UHFFFAOYSA-N
in ch i: InChI=1S/C20H24ClN3S/c1-22-11-13-23(14-12-22)9-4-10-24-17-5-2-3-6-19(17)25-20-8-7-16(21)15-18(20)24/h2-3,5-8,15H,4,9-14H2,1H3
comment: Prochlorperazine is a potent phenothiazine neuroleptic.
iupac name: 2-chloro-10-[3-(4-methylpiperazin-1-yl)propyl]-10H-phenothiazine
xref: CHEMBL728
synonym: Compro
synonym: Procomp
synonym: Prochlorperazine
synonym: Compazine®
synonym: prochlorperazine edisylate
synonym: prochlorperazine maleate
synonym: Buccastem®
approved: t
ligand name: prochlorperazine
type: SyntheticOrganicLigand

procarbazine
canonical SMILES: CNNCc1ccc(cc1)C(=O)NC(C)C
isomeric SMILES: CNNCc1ccc(cc1)C(=O)NC(C)C
in ch i key: CPTBDICYNRMXFX-UHFFFAOYSA-N
in ch i: InChI=1S/C12H19N3O/c1-9(2)15-12(16)11-6-4-10(5-7-11)8-14-13-3/h4-7,9,13-14H,8H2,1-3H3,(H,15,16)
comment: Procarbazine is a DNA alkylating agent.
iupac name: 4-[(2-methylhydrazin-1-yl)methyl]-N-(propan-2-yl)benzamide
xref: CHEMBL1321
synonym: Matulane®
synonym: Ro-4646711
synonym: Ro-4-6467/1
approved: t
ligand name: procarbazine
type: SyntheticOrganicLigand

probucol
in ch i key: FYPMFJGVHOHGLL-UHFFFAOYSA-N
in ch i: InChI=1S/C31H48O2S2/c1-27(2,3)21-15-19(16-22(25(21)32)28(4,5)6)34-31(13,14)35-20-17-23(29(7,8)9)26(33)24(18-20)30(10,11)12/h15-18,32-33H,1-14H3
comment: Probucol is a lipid-lowering drug. Marketing of this drug was ceased in 1995 in the US due to safety concerns.
iupac name: 2,6-di-tert-butyl-4-({2-[(3,5-di-tert-butyl-4-hydroxyphenyl)sulfanyl]propan-2-yl}sulfanyl)phenol
xref: CHEMBL608
synonym: Bisbid
synonym: Sinlestal
synonym: Lorelco®
synonym: DH-581
approved: t
ligand name: probucol
type: SyntheticOrganicLigand

prilocaine
canonical SMILES: CCCNC(C(=Nc1ccccc1C)O)C
isomeric SMILES: CCCNC(C(=Nc1ccccc1C)O)C
in ch i key: MVFGUOIZUNYYSO-UHFFFAOYSA-N
in ch i: InChI=1S/C13H20N2O/c1-4-9-14-11(3)13(16)15-12-8-6-5-7-10(12)2/h5-8,11,14H,4,9H2,1-3H3,(H,15,16)
comment: Prilocaine is often an active ingredient in fixed-mixture medications along with <Ligand id=2623/>. Marketed formulations may contain prilocaine hydrochloride (PubChem CID 92163).
iupac name: N-(2-methylphenyl)-2-(propylamino)propanimidic acid
xref: CHEMBL1194
synonym: ASTRA 1512
synonym: L-67
synonym: Citanest Plain
synonym: Citanest Plain Dental
synonym: Citanest®
synonym: Prilotekal®
approved: t
ligand name: prilocaine
type: SyntheticOrganicLigand

prazepam
in ch i key: MWQCHHACWWAQLJ-UHFFFAOYSA-N
in ch i: InChI=1S/C19H17ClN2O/c20-15-8-9-17-16(10-15)19(14-4-2-1-3-5-14)21-11-18(23)22(17)12-13-6-7-13/h1-5,8-10,13H,6-7,11-12H2
comment: Prazepam is a benzodiazepine type drug.
iupac name: 7-chloro-1-(cyclopropylmethyl)-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepin-2-one
xref: CHEMBL969
synonym: Centrax®
synonym: W-4020
synonym: Centrac
synonym: Demetrin
synonym: Pozapam
synonym: Prasepine
approved: t
ligand name: prazepam
type: SyntheticOrganicLigand

polythiazide
in ch i key: CYLWJCABXYDINA-UHFFFAOYSA-N
comment: Polythiazide is a thiazide diuretic.
iupac name: 6-chloro-2-methyl-1,1-dioxo-3-(2,2,2-trifluoroethylsulfanylmethyl)-3,4-dihydrobenzo[e][1,2,4]thiadiazine-7-sulfonamide
xref: CHEMBL1587
synonym: P-2525
synonym: Renese®
approved: t
ligand name: polythiazide
type: SyntheticOrganicLigand

piroxicam
in ch i key: QYSPLQLAKJAUJT-UHFFFAOYSA-N
in ch i: InChI=1S/C15H13N3O4S/c1-18-13(15(20)17-12-8-4-5-9-16-12)14(19)10-6-2-3-7-11(10)23(18,21)22/h2-9,19H,1H3,(H,16,17,20)
comment: Piroxicam is a nonsteroidal anti-inflammatory drug (NSAID) with analgesic and antipyretic activity. Drug formulations contain β-cyclodextrin to increase bioavailability eg piroxicam betadex has PubChem CID 54723875.
iupac name: 4-hydroxy-2-methyl-1,1-dioxo-N-pyridin-2-yl-1λ6,2-benzothiazine-3-carboxamide
xref: CHEMBL527
synonym: CP-16171
synonym: Feldene®
synonym: Brexidol
synonym: Candyl
approved: t
ligand name: piroxicam
type: SyntheticOrganicLigand

pirbuterol
canonical SMILES: OCc1nc(ccc1O)C(CNC(C)(C)C)O
isomeric SMILES: OCc1nc(ccc1O)C(CNC(C)(C)C)O
in ch i key: VQDBNKDJNJQRDG-UHFFFAOYSA-N
in ch i: InChI=1S/C12H20N2O3/c1-12(2,3)13-6-11(17)8-4-5-10(16)9(7-15)14-8/h4-5,11,13,15-17H,6-7H2,1-3H3
comment: Marketed formulations may contain (PubChem CID 171674).
iupac name: 6-[2-(tert-butylamino)-1-hydroxyethyl]-2-(hydroxymethyl)pyridin-3-ol
xref: CHEMBL1094966
synonym: CP-24314-1
synonym: CP-2431414
synonym: CP-24314-14
synonym: Maxair Autohaler
synonym: Maxair®
approved: t
ligand name: pirbuterol
type: SyntheticOrganicLigand

pipobroman
canonical SMILES: BrCCC(=O)N1CCN(CC1)C(=O)CCBr
isomeric SMILES: BrCCC(=O)N1CCN(CC1)C(=O)CCBr
in ch i key: NJBFOOCLYDNZJN-UHFFFAOYSA-N
comment: This is a DNA alkylating agent.
iupac name: 3-bromo-1-[4-(3-bromopropanoyl)piperazin-1-yl]propan-1-one
xref: CHEMBL1585
synonym: A-8103
synonym: Vercyte®
synonym: Vercite
approved: t
ligand name: pipobroman
type: SyntheticOrganicLigand

phenylbutazone
canonical SMILES: CCCCC1C(=O)N(N(C1=O)c1ccccc1)c1ccccc1
isomeric SMILES: CCCCC1C(=O)N(N(C1=O)c1ccccc1)c1ccccc1
in ch i key: VYMDGNCVAMGZFE-UHFFFAOYSA-N
in ch i: InChI=1S/C19H20N2O2/c1-2-3-14-17-18(22)20(15-10-6-4-7-11-15)21(19(17)23)16-12-8-5-9-13-16/h4-13,17H,2-3,14H2,1H3
comment: Phenylbutazone was historically used as a nonsteroidal anti-inflammatory drug (NSAID). Although no longer approved for use in humans, this compound is widely used in animals to reduce muscular damage and inflammation. More recently, phenylbutazone, or 'bute', found notoriety as an illegal contaminant found in some meat samples tested in the European horse meat scandal of 2013. The UK Foods Standards Agency issued this statement regarding bute contamination.
iupac name: 4-butyl-1,2-diphenylpyrazolidine-3,5-dione
xref: CHEMBL101
synonym: Azolid
synonym: Antadol
synonym: Elmedal
synonym: Butaject
synonym: Equiphar
synonym: Pro-Bute
synonym: Phenylbutazone
synonym: Butazolidine®
approved: t
ligand name: phenylbutazone
type: SyntheticOrganicLigand

penbutolol
canonical SMILES: OC(COc1ccccc1C1CCCC1)CNC(C)(C)C
isomeric SMILES: O[C@H](COc1ccccc1C1CCCC1)CNC(C)(C)C
in ch i key: KQXKVJAGOJTNJS-HNNXBMFYSA-N
in ch i: InChI=1S/C18H29NO2/c1-18(2,3)19-12-15(20)13-21-17-11-7-6-10-16(17)14-8-4-5-9-14/h6-7,10-11,14-15,19-20H,4-5,8-9,12-13H2,1-3H3/t15-/m0/s1
comment: Penbutolol is a β-adrenoceptor antagonist (β-blocker).
iupac name: tert-butyl[(2S)-3-(2-cyclopentylphenoxy)-2-hydroxypropyl]amine
xref: CHEMBL1290
synonym: HOE-893d
synonym: HOE-39-893d
synonym: Levatol®
approved: t
ligand name: penbutolol
type: SyntheticOrganicLigand

pargyline
canonical SMILES: CN(Cc1ccccc1)CC#C
isomeric SMILES: CN(Cc1ccccc1)CC#C
in ch i key: DPWPWRLQFGFJFI-UHFFFAOYSA-N
in ch i: InChI=1S/C11H13N/c1-3-9-12(2)10-11-7-5-4-6-8-11/h1,4-8H,9-10H2,2H3
comment: Pargyline is a monoamine oxidase inhibitor (MAOI).
iupac name: benzyl(methyl)(prop-2-yn-1-yl)amine
xref: CHEMBL673
synonym: A-19120
synonym: MO-911
synonym: Eutonyl®
approved: t
ligand name: pargyline
type: SyntheticOrganicLigand

paramethadione
canonical SMILES: CCC1(C)OC(=O)N(C1=O)C
isomeric SMILES: CCC1(C)OC(=O)N(C1=O)C
in ch i key: VQASKUSHBVDKGU-UHFFFAOYSA-N
in ch i: InChI=1S/C7H11NO3/c1-4-7(2)5(9)8(3)6(10)11-7/h4H2,1-3H3
comment: Paramethadione is an anticonvulsant drug.
iupac name: 5-ethyl-3,5-dimethyl-1,3-oxazolidine-2,4-dione
xref: CHEMBL1100
synonym: isoethadione
synonym: Paradione®
approved: t
ligand name: paramethadione
type: SyntheticOrganicLigand

pantoprazole
in ch i key: IQPSEEYGBUAQFF-UHFFFAOYSA-N
comment: Pantoprazole is a proton pump inhibitor. Marketed formulations may contain pantoprazole sodium (PubChem CID 15008962) or pantoprazole sodium sesquihydrate (PubChem CID 23690067).
iupac name: 6-(difluoromethoxy)-2-[(3,4-dimethoxypyridin-2-yl)methanesulfinyl]-1H-1,3-benzodiazole
xref: CHEMBL1502
synonym: BY-1023
synonym: SK-96022
synonym: Protonix Iv
synonym: Protonix®
approved: t
ligand name: pantoprazole
type: SyntheticOrganicLigand

pamidronic acid
canonical SMILES: NCCC(P(=O)(O)O)(P(=O)(O)O)O
isomeric SMILES: NCCC(P(=O)(O)O)(P(=O)(O)O)O
in ch i key: WRUUGTRCQOWXEG-UHFFFAOYSA-N
in ch i: InChI=1S/C3H11NO7P2/c4-2-1-3(5,12(6,7)8)13(9,10)11/h5H,1-2,4H2,(H2,6,7,8)(H2,9,10,11)
comment: Pamidronic acid is a bisphosphonate drug.
iupac name: (3-amino-1-hydroxy-1-phosphonopropyl)phosphonic acid
xref: CHEMBL834
synonym: disodium pamidronate
synonym: Aredia®
synonym: CGP-23339AE
approved: t
ligand name: pamidronic acid
type: SyntheticOrganicLigand

paliperidone
in ch i key: PMXMIIMHBWHSKN-UHFFFAOYSA-N
in ch i: InChI=1S/C23H27FN4O3/c1-14-17(23(30)28-9-2-3-19(29)22(28)25-14)8-12-27-10-6-15(7-11-27)21-18-5-4-16(24)13-20(18)31-26-21/h4-5,13,15,19,29H,2-3,6-12H2,1H3
comment: Paliperidone is an atypical antipsychotic. Mechanistically it is a dopamine receptor and 5-HT2A receptor antagonist.
iupac name: 3-{2-[4-(6-fluoro-1,2-benzoxazol-3-yl)piperidin-1-yl]ethyl}-9-hydroxy-2-methyl-4H,6H,7H,8H,9H-pyrido[1,2-a]pyrimidin-4-one
xref: CHEMBL1621
synonym: 9-hydroxyrisperidone
synonym: Invega Sustenna
synonym: Invega®
synonym: Ro-76477
synonym: Ro-92670
approved: t
ligand name: paliperidone
type: SyntheticOrganicLigand

oxyphenonium
canonical SMILES: CC[N+](CCOC(=O)C(c1ccccc1)(C1CCCCC1)O)(CC)C
isomeric SMILES: CC[N+](CCOC(=O)C(c1ccccc1)(C1CCCCC1)O)(CC)C
in ch i key: GFRUPHOKLBPHTQ-UHFFFAOYSA-N
in ch i: InChI=1S/C21H34NO3/c1-4-22(3,5-2)16-17-25-20(23)21(24,18-12-8-6-9-13-18)19-14-10-7-11-15-19/h6,8-9,12-13,19,24H,4-5,7,10-11,14-17H2,1-3H3/q+1
comment: Oxyphenonium is a synthetic anticholinergic drug with gastrointestinal antispasmodic and antisecretory action.
xref: CHEMBL1201286
synonym: Antrenyl
synonym: oxyphenonium bromide
approved: t
ligand name: oxyphenonium
type: SyntheticOrganicLigand

oxyphencyclimine
canonical SMILES: CN1CCCN=C1COC(=O)C(c1ccccc1)(C1CCCCC1)O
isomeric SMILES: CN1CCCN=C1COC(=O)C(c1ccccc1)(C1CCCCC1)O
in ch i key: DUDKAZCAISNGQN-UHFFFAOYSA-N
in ch i: InChI=1S/C20H28N2O3/c1-22-14-8-13-21-18(22)15-25-19(23)20(24,16-9-4-2-5-10-16)17-11-6-3-7-12-17/h2,4-5,9-10,17,24H,3,6-8,11-15H2,1H3
comment: Oxyphencyclimine is a synthetic anticholinergic drug with gastrointestinal antispasmodic and antisecretory action.
iupac name: (1-methyl-1,4,5,6-tetrahydropyrimidin-2-yl)methyl 2-cyclohexyl-2-hydroxy-2-phenylacetate
xref: CHEMBL1495
synonym: Daricon
approved: t
ligand name: oxyphencyclimine
type: SyntheticOrganicLigand

oxprenolol
canonical SMILES: C=CCOc1ccccc1OCC(CNC(C)C)O
isomeric SMILES: C=CCOc1ccccc1OCC(CNC(C)C)O
in ch i key: CEMAWMOMDPGJMB-UHFFFAOYSA-N
in ch i: InChI=1S/C15H23NO3/c1-4-9-18-14-7-5-6-8-15(14)19-11-13(17)10-16-12(2)3/h4-8,12-13,16-17H,1,9-11H2,2-3H3
comment: Oxprenolol is a β-adrenoceptor antagonist (β-blocker).
iupac name: {2-hydroxy-3-[2-(prop-2-en-1-yloxy)phenoxy]propyl}(propan-2-yl)amine
xref: CHEMBL546
synonym: BA-39089
synonym: Captol
synonym: Coretal
synonym: Laracor
synonym: Tevacor
synonym: Corbeton
synonym: Trasicor
synonym: Trasidex
synonym: Slow-Pren
synonym: Trasitensin
synonym: Slow-Trasicor
synonym: Trasacor®
approved: t
ligand name: oxprenolol
type: SyntheticOrganicLigand

oxcarbazepine
canonical SMILES: O=C1Cc2ccccc2N(c2c1cccc2)C(=N)O
isomeric SMILES: O=C1Cc2ccccc2N(c2c1cccc2)C(=N)O
in ch i key: CTRLABGOLIVAIY-UHFFFAOYSA-N
in ch i: InChI=1S/C15H12N2O2/c16-15(19)17-12-7-3-1-5-10(12)9-14(18)11-6-2-4-8-13(11)17/h1-8H,9H2,(H2,16,19)
comment: Oxcarbazepine is an anticonvulsant and antiepileptic drug.
iupac name: 5-oxo-6H-benzo[b][1]benzazepine-11-carboxamide
xref: CHEMBL1068
synonym: GP-47680
synonym: KIN-493
synonym: Oxtellar Xr
synonym: Oxcarbazepine
synonym: Trileptal®
approved: t
ligand name: oxcarbazepine
type: SyntheticOrganicLigand

metaraminol
canonical SMILES: CC(C(c1cccc(c1)O)O)N
isomeric SMILES: C[C@@H]([C@@H](c1cccc(c1)O)O)N
in ch i key: WXFIGDLSSYIKKV-RCOVLWMOSA-N
in ch i: InChI=1S/C9H13NO2/c1-6(10)9(12)7-3-2-4-8(11)5-7/h2-6,9,11-12H,10H2,1H3/t6-,9-/m0/s1
comment: Metaraminol is the (1R,2S) stereoisomer of the racemate meta-hydroxynorephedrine (3,β-dihydroxyamphetamine; PubChem CID 4087).
iupac name: 3-[(1R,2S)-2-amino-1-hydroxypropyl]phenol
xref: CHEMBL1201319
synonym: metaraminol bitartrate
synonym: Aramine®
synonym: metaradrine
synonym: Metaramin
synonym: Pressonex
approved: t
ligand name: metaraminol
type: SyntheticOrganicLigand

olopatadine
canonical SMILES: CN(CCC=C1c2cc(ccc2OCc2c1cccc2)CC(=O)O)C
in ch i key: JBIMVDZLSHOPLA-LSCVHKIXSA-N
in ch i: InChI=1S/C21H23NO3/c1-22(2)11-5-8-18-17-7-4-3-6-16(17)14-25-20-10-9-15(12-19(18)20)13-21(23)24/h3-4,6-10,12H,5,11,13-14H2,1-2H3,(H,23,24)/b18-8-
comment: Olopatadine is an antihistamine. Marketed formulations may contain olopatadine hydrochloride (PubChem CID 5282402).
iupac name: 2-[(11Z)-11-[3-(dimethylamino)propylidene]-6H-benzo[c][1]benzoxepin-2-yl]acetic acid
xref: CHEMBL1189432
synonym: Pazeo®
synonym: Opatanol®
synonym: KW-4679
synonym: ALO-4943A
synonym: Pataday
synonym: Patanase
synonym: Patanol®
approved: t
ligand name: olopatadine
type: SyntheticOrganicLigand

nizatidine
canonical SMILES: CNC(=CN(=O)=O)NCCSCc1csc(n1)CN(C)C
isomeric SMILES: CN/C(=C/N(=O)=O)/NCCSCc1csc(n1)CN(C)C
in ch i key: SGXXNSQHWDMGGP-IZZDOVSWSA-N
in ch i: InChI=1S/C12H21N5O2S2/c1-13-11(6-17(18)19)14-4-5-20-8-10-9-21-12(15-10)7-16(2)3/h6,9,13-14H,4-5,7-8H2,1-3H3/b11-6+
comment: Nizatidine is a histamine H2 receptor antagonist. It is structurally related to <Ligand id=1234/> but has a thiazole ring substitution in place of the furan ring in ranitidine. Nizatidine was the last new histamine H2 receptor antagonist to be approved prior to proton pump inhibitors reaching the clinic.
xref: CHEMBL653
synonym: Axid ar
synonym: Nizatidine
synonym: Axid®
synonym: LY-139037
approved: t
ligand name: nizatidine
type: SyntheticOrganicLigand

nefazodone
in ch i key: VRBKIVRKKCLPHA-UHFFFAOYSA-N
in ch i: InChI=1S/C25H32ClN5O2/c1-2-24-27-31(25(32)30(24)18-19-33-23-10-4-3-5-11-23)13-7-12-28-14-16-29(17-15-28)22-9-6-8-21(26)20-22/h3-6,8-11,20H,2,7,12-19H2,1H3
comment: Nefazodone is an antidepressant. Marketed formulations may contain nefazodone hydrochloride (PubChem CID 54911).
iupac name: 1-{3-[4-(3-chlorophenyl)piperazin-1-yl]propyl}-3-ethyl-4-(2-phenoxyethyl)-4,5-dihydro-1H-1,2,4-triazol-5-one
xref: CHEMBL623
synonym: BMY-13754
synonym: MJ-13754-1
synonym: Serzone
synonym: Nefadar®
synonym: Rulivan
synonym: Dutonin
approved: t
ligand name: nefazodone
type: SyntheticOrganicLigand

nebivolol
in ch i key: KOHIRBRYDXPAMZ-UHFFFAOYSA-N
in ch i: InChI=1S/C22H25F2NO4/c23-15-3-7-19-13(9-15)1-5-21(28-19)17(26)11-25-12-18(27)22-6-2-14-10-16(24)4-8-20(14)29-22/h3-4,7-10,17-18,21-22,25-27H,1-2,5-6,11-12H2
comment: Nebivolol is a β-blocker, selective for β1-adrenoceptors. Marketed formulations may contain nebivolol hydrochloride (PubChem CID ).
iupac name: 1-(6-fluoro-3,4-dihydro-2H-1-benzopyran-2-yl)-2-{[2-(6-fluoro-3,4-dihydro-2H-1-benzopyran-2-yl)-2-hydroxyethyl]amino}ethan-1-ol
xref: CHEMBL434394
synonym: Bystolic®
synonym: R-65824
synonym: Ro-67555
synonym: Nebilet
approved: t
ligand name: nebivolol
type: SyntheticOrganicLigand

nabumetone
canonical SMILES: COc1ccc2c(c1)ccc(c2)CCC(=O)C
isomeric SMILES: COc1ccc2c(c1)ccc(c2)CCC(=O)C
in ch i key: BLXXJMDCKKHMKV-UHFFFAOYSA-N
in ch i: InChI=1S/C15H16O2/c1-11(16)3-4-12-5-6-14-10-15(17-2)8-7-13(14)9-12/h5-10H,3-4H2,1-2H3
comment: Nabumetone is a non-steroidal anti-inflammatory drug (NSAID). Nabumetone is a prodrug metabilosed to the active component, 6-methoxy-2-naphthylacetic acid (6MNA; CHEMBL1105)
iupac name: 4-(6-methoxynaphthalen-2-yl)butan-2-one
xref: CHEMBL1070
synonym: BRL-14777
synonym: Relafen®
synonym: Relifex
synonym: Gambaran
approved: t
ligand name: nabumetone
type: SyntheticOrganicLigand

moracizine
in ch i key: FUBVWMNBEHXPSU-UHFFFAOYSA-N
in ch i: InChI=1S/C22H25N3O4S/c1-2-29-22(27)23-16-7-8-20-18(15-16)25(17-5-3-4-6-19(17)30-20)21(26)9-10-24-11-13-28-14-12-24/h3-8,15H,2,9-14H2,1H3,(H,23,27)
comment: Moracizine is a phenothiazine derivative class Ic antiarrhythmic drug. Marketing by the original manufacturer has been discontinued.
iupac name: N-{10-[3-(morpholin-4-yl)propanoyl]-10H-phenothiazin-2-yl}ethoxycarboximidic acid
xref: CHEMBL1075
synonym: EN-313
synonym: Ethmozine®
synonym: moricizine
approved: t
ligand name: moracizine
type: SyntheticOrganicLigand

mivacurium
in ch i key: ILVYCEVXHALBSC-OTBYEXOQSA-N
in ch i: InChI=1S/C58H80N2O14/c1-59(25-21-41-35-47(63-3)49(65-5)37-43(41)45(59)29-39-31-51(67-7)57(71-11)52(32-39)68-8)23-17-27-73-55(61)19-15-13-14-16-20-56(62)74-28-18-24-60(2)26-22-42-36-48(64-4)50(66-6)38-44(42)46(60)30-40-33-53(69-9)58(72-12)54(34-40)70-10/h13-14,31-38,45-46H,15-30H2,1-12H3/q+2/b14-13+/t45-,46-,59?,60?/m1/s1
comment: Mivacurium is a short-acting, nondepolarizing skeletal muscle relaxant.
iupac name: (1R)-2-(3-{[(4E)-8-{3-[(1R)-6,7-dimethoxy-2-methyl-1-[(3,4,5-trimethoxyphenyl)methyl]-1,2,3,4-tetrahydroisoquinolin-2-ium-2-yl]propoxy}-8-oxooct-4-enoyl]oxy}propyl)-6,7-dimethoxy-2-methyl-1-[(3,4,5-trimethoxyphenyl)methyl]-1,2,3,4-tetrahydroisoquinolin-2-ium
xref: CHEMBL1182833
synonym: BWB109OU
synonym: Mivacron®
approved: t
ligand name: mivacurium
type: SyntheticOrganicLigand

mitoxantrone
in ch i key: KKZJGLLVHKMTCM-UHFFFAOYSA-N
in ch i: InChI=1S/C22H28N4O6/c27-11-9-23-5-7-25-13-1-2-14(26-8-6-24-10-12-28)18-17(13)21(31)19-15(29)3-4-16(30)20(19)22(18)32/h1-4,23-30H,5-12H2
comment: Marketed formulations may contain mitoxantrone hydrochloride (PubChem CID 5458171).
iupac name: 1,4-dihydroxy-5,8-bis({2-[(2-hydroxyethyl)amino]ethyl}amino)-9,10-dihydroanthracene-9,10-dione
xref: CHEMBL58
synonym: CL-232315
synonym: Novantrone®
approved: t
ligand name: mitoxantrone
type: SyntheticOrganicLigand

mirtazapine
canonical SMILES: CN1CCN2C(C1)c1ccccc1Cc1c2nccc1
isomeric SMILES: CN1CCN2C(C1)c1ccccc1Cc1c2nccc1
in ch i key: RONZAEMNMFQXRA-UHFFFAOYSA-N
in ch i: InChI=1S/C17H19N3/c1-19-9-10-20-16(12-19)15-7-3-2-5-13(15)11-14-6-4-8-18-17(14)20/h2-8,16H,9-12H2,1H3
comment: Mirtazapine is a tetracyclic antidepressant with complex polypharmacology involving certain adrenergic and serotonin receptors <Reference id=40306/>. It also has strong antihistamine effects.
xref: CHEMBL654
synonym: ORG-3770
synonym: Remeron Soltab
synonym: Remeron®
synonym: Avanza
synonym: Axit
synonym: Mirtazon
synonym: Zispin
approved: t
ligand name: mirtazapine
type: SyntheticOrganicLigand

midodrine
canonical SMILES: COc1ccc(cc1C(CN=C(CN)O)O)OC
isomeric SMILES: COc1ccc(cc1C(CN=C(CN)O)O)OC
in ch i key: PTKSEFOSCHHMPD-UHFFFAOYSA-N
in ch i: InChI=1S/C12H18N2O4/c1-17-8-3-4-11(18-2)9(5-8)10(15)7-14-12(16)6-13/h3-5,10,15H,6-7,13H2,1-2H3,(H,14,16)
comment: The active metabolite of midodrine is desglymidodrine (CHEMBL1076). Marketed formulations may contain midodrine hydrochloride (PubChem CID 18340).
iupac name: 2-amino-N-[2-(2,5-dimethoxyphenyl)-2-hydroxyethyl]ethanimidic acid
xref: CHEMBL1201212
synonym: A-4020 Linz
synonym: ST-1085
synonym: Orvaten
synonym: Proamatine®
approved: t
ligand name: midodrine
type: SyntheticOrganicLigand

alimemazine
canonical SMILES: CN(CC(CN1c2ccccc2Sc2c1cccc2)C)C
isomeric SMILES: CN(CC(CN1c2ccccc2Sc2c1cccc2)C)C
in ch i key: ZZHLYYDVIOPZBE-UHFFFAOYSA-N
in ch i: InChI=1S/C18H22N2S/c1-14(12-19(2)3)13-20-15-8-4-6-10-17(15)21-18-11-7-5-9-16(18)20/h4-11,14H,12-13H2,1-3H3
comment: Alimemazine is a phenothiazine derivative antihistamine.
iupac name: dimethyl[2-methyl-3-(10H-phenothiazin-10-yl)propyl]amine
xref: CHEMBL829
synonym: methylpromazine
synonym: Temaril
synonym: Vanectyl
synonym: Vallergan
synonym: Trimeprazine Tartrate
synonym: trimeprazine
synonym: Nedeltran®
synonym: Panectyl
synonym: Repeltin
synonym: Therafene
synonym: Theralen
approved: t
ligand name: alimemazine
type: SyntheticOrganicLigand

methylphenidate
canonical SMILES: COC(=O)C(c1ccccc1)C1CCCCN1
isomeric SMILES: COC(=O)C(c1ccccc1)C1CCCCN1
in ch i key: DUGOZIWVEXMGBE-UHFFFAOYSA-N
in ch i: InChI=1S/C14H19NO2/c1-17-14(16)13(11-7-3-2-4-8-11)12-9-5-6-10-15-12/h2-4,7-8,12-13,15H,5-6,9-10H2,1H3
comment: Methylphenidate is a racemic mixture of optical isomers (enantiomers). We show the chemical structure without specified stereochemistry to represent the mixture. The most active (R,R) enantiomer is the approved drug <Ligand id=7554/>. Methylphenidate is administered as the hydrochloride salt (PubChem CID 9280).
iupac name: methyl 2-phenyl-2-(piperidin-2-yl)acetate
xref: CHEMBL796
synonym: Jornay PM® (a.k.a. HLD200)
synonym: Daytrana
synonym: Methylin
synonym: Ritalin LA
synonym: Ritalin La
synonym: Ritalin SR
synonym: Metadate CD
synonym: Metadate ER
synonym: Methylin ER
synonym: Quillivant XR
synonym: Methylphenidate Hydrochloride
synonym: Concerta®
synonym: Ritalin®
approved: t
ligand name: methylphenidate
type: SyntheticOrganicLigand

methyclothiazide
in ch i key: CESYKOGBSMNBPD-UHFFFAOYSA-N
comment: Methyclothiazide is a diuretic.
iupac name: 6-chloro-3-(chloromethyl)-2-methyl-1,1-dioxo-3,4-dihydro-1$l^{6},2,4-benzothiadiazine-7-sulfonamide
xref: CHEMBL1577
synonym: Enduron®
synonym: Aquatensen®
approved: t
ligand name: methyclothiazide
type: SyntheticOrganicLigand

methoxyflurane
canonical SMILES: COC(C(Cl)Cl)(F)F
isomeric SMILES: COC(C(Cl)Cl)(F)F
in ch i key: RFKMCNOHBTXSMU-UHFFFAOYSA-N
in ch i: InChI=1S/C3H4Cl2F2O/c1-8-3(6,7)2(4)5/h2H,1H3
comment: Methoxyflurane is a halogenated ether volatile inhalational anaesthetic. In the US it was withdrawn from the market for safety concerns (it is nephrotoxic and hepatotoxic) but is still available/used in other countries, including the UK (for emergency relief of moderate to severe pain in conscious adult patients as a result of trauma).
iupac name: 2,2-dichloro-1,1-difluoro-1-methoxyethane
xref: CHEMBL1341
synonym: Metofane
synonym: Pentrane
synonym: Penthrane®
approved: t
ligand name: methoxyflurane
type: SyntheticOrganicLigand

methohexital
canonical SMILES: C=CCC1(C(C#CCC)C)C(=NC(=O)N(C1=O)C)O
isomeric SMILES: C=CCC1(C(C#CCC)C)C(=NC(=O)N(C1=O)C)O
in ch i key: NZXKDOXHBHYTKP-UHFFFAOYSA-N
in ch i: InChI=1S/C14H18N2O3/c1-5-7-8-10(3)14(9-6-2)11(17)15-13(19)16(4)12(14)18/h6,10H,2,5,9H2,1,3-4H3,(H,15,17,19)
comment: Methohexital is a barbiturate.
iupac name: 5-(hex-3-yn-2-yl)-6-hydroxy-3-methyl-5-(prop-2-en-1-yl)-2,3,4,5-tetrahydropyrimidine-2,4-dione
xref: CHEMBL7413
synonym: Brietal
synonym: Brevimytal
synonym: Brevital Sodium
synonym: Brevital®
synonym: methohexitone
approved: t
ligand name: methohexital
type: SyntheticOrganicLigand

methixene
canonical SMILES: CN1CCCC(C1)CC1c2ccccc2Sc2c1cccc2
isomeric SMILES: CN1CCCC(C1)CC1c2ccccc2Sc2c1cccc2
in ch i key: MJFJKKXQDNNUJF-UHFFFAOYSA-N
in ch i: InChI=1S/C20H23NS/c1-21-12-6-7-15(14-21)13-18-16-8-2-4-10-19(16)22-20-11-5-3-9-17(18)20/h2-5,8-11,15,18H,6-7,12-14H2,1H3
comment: Methixene is an antihistamine drug, with anticholinergic activity. There is no information regarding approval for clinical use of this drug on the US FDA website. Other national approval agencies may have granted marketing authorisation.
iupac name: 1-methyl-3-(9H-thioxanthen-9-ylmethyl)piperidine
xref: CHEMBL1201342
synonym: SJ-1977
synonym: metixene
synonym: Trest®
approved: t
ligand name: methixene
type: SyntheticOrganicLigand

methdilazine
canonical SMILES: CN1CCC(C1)CN1c2ccccc2Sc2c1cccc2
isomeric SMILES: CN1CCC(C1)CN1c2ccccc2Sc2c1cccc2
in ch i key: HTMIBDQKFHUPSX-UHFFFAOYSA-N
in ch i: InChI=1S/C18H20N2S/c1-19-11-10-14(12-19)13-20-15-6-2-4-8-17(15)21-18-9-5-3-7-16(18)20/h2-9,14H,10-13H2,1H3
comment: Methdilazine is an antihistamine drug, with anticholinergic activity.
iupac name: 10-[(1-methylpyrrolidin-3-yl)methyl]-10H-phenothiazine
xref: CHEMBL1200959
synonym: methdilazine hydrochloride
synonym: Tacaryl®
approved: t
ligand name: methdilazine
type: SyntheticOrganicLigand

mesoridazine
canonical SMILES: CN1CCCCC1CCN1c2ccccc2Sc2c1cc(cc2)S(=O)C
isomeric SMILES: CN1CCCCC1CCN1c2ccccc2Sc2c1cc(cc2)S(=O)C
in ch i key: SLVMESMUVMCQIY-UHFFFAOYSA-N
in ch i: InChI=1S/C21H26N2OS2/c1-22-13-6-5-7-16(22)12-14-23-18-8-3-4-9-20(18)25-21-11-10-17(26(2)24)15-19(21)23/h3-4,8-11,15-16H,5-7,12-14H2,1-2H3
comment: The approved drug contains a racemic mixture of enantiomers <Reference id=24264/>. The four possible isomers are depicted in PubChem CID 76960490. We show the non-isomeric molecule to represent this mixture.
iupac name: 10-[2-(1-methylpiperidin-2-yl)ethyl]-2-methylsulfinylphenothiazine
xref: CHEMBL1088
synonym: NC-123
synonym: TPS-23
synonym: Serentil®
approved: t
ligand name: mesoridazine
type: SyntheticOrganicLigand

mercaptopurine
canonical SMILES: Sc1ncnc2c1nc[nH]2
isomeric SMILES: Sc1ncnc2c1nc[nH]2
in ch i key: GLVAUDGFNGKCSF-UHFFFAOYSA-N
in ch i: InChI=1S/C5H4N4S/c10-5-3-4(7-1-6-3)8-2-9-5/h1-2H,(H2,6,7,8,9,10)
comment: Mercaptopurine has immunosuppressive action as well as antineoplastic activity.
iupac name: 9H-purine-6-thiol
xref: CHEMBL1425
synonym: Xaluprine®
synonym: Leukerin
synonym: Mercaleukin
synonym: Mercaptopurine
synonym: Purinethol®
synonym: 6-mercaptopurine
approved: t
ligand name: mercaptopurine
type: SyntheticOrganicLigand

meprobamate
canonical SMILES: CCCC(COC(=N)O)(COC(=N)O)C
isomeric SMILES: CCCC(COC(=N)O)(COC(=N)O)C
in ch i key: NPPQSCRMBWNHMW-UHFFFAOYSA-N
in ch i: InChI=1S/C9H18N2O4/c1-3-4-9(2,5-14-7(10)12)6-15-8(11)13/h3-6H2,1-2H3,(H2,10,12)(H2,11,13)
comment: Meprobamate is a carbamate derivative anxiolytic drug. Use of meprobamate has largely been replaced by the benzodiazepines due to their wider therapeutic index and lower incidence of serious side-effects.
iupac name: ({2-[(C-hydroxycarbonimidoyloxy)methyl]-2-methylpentyl}oxy)carboximidic acid
xref: CHEMBL979
synonym: Amosene
synonym: Bamate
synonym: Mepriam
synonym: Tranmep
synonym: Neuramate
synonym: Miltown®
synonym: Equanil®
synonym: Meprospan®
approved: t
ligand name: meprobamate
type: SyntheticOrganicLigand

mepivacaine
canonical SMILES: CN1CCCCC1C(=Nc1c(C)cccc1C)O
isomeric SMILES: CN1CCCCC1C(=Nc1c(C)cccc1C)O
in ch i key: INWLQCZOYSRPNW-UHFFFAOYSA-N
in ch i: InChI=1S/C15H22N2O/c1-11-7-6-8-12(2)14(11)16-15(18)13-9-4-5-10-17(13)3/h6-8,13H,4-5,9-10H2,1-3H3,(H,16,18)
comment: Mepivacaine is an amide class local anesthetic. It is a racemic mixture of enantiomers. We show the chemical structure without specified stereochemistry to represent the mixture.
iupac name: N-(2,6-dimethylphenyl)-1-methylpiperidine-2-carboximidic acid
xref: CHEMBL1087
synonym: Polocaine-Mpf
synonym: Scandonest Plain
synonym: Isocaine Hydrochloride
synonym: Arestocaine Hydrochloride
synonym: Carbocaine®
synonym: Polocaine®
synonym: mepivacaine hydrochloride
approved: t
ligand name: mepivacaine
type: SyntheticOrganicLigand

mephenytoin
canonical SMILES: CCC1(N=C(N(C1=O)C)O)c1ccccc1
isomeric SMILES: CCC1(N=C(N(C1=O)C)O)c1ccccc1
in ch i key: GMHKMTDVRCWUDX-UHFFFAOYSA-N
in ch i: InChI=1S/C12H14N2O2/c1-3-12(9-7-5-4-6-8-9)10(15)14(2)11(16)13-12/h4-8H,3H2,1-2H3,(H,13,16)
comment: Mephenytoin is a hydantoin class drug. It is no longer available in the US or the UK.
iupac name: 4-ethyl-2-hydroxy-1-methyl-4-phenyl-4,5-dihydro-1H-imidazol-5-one
xref: CHEMBL861
synonym: Mesantoin®
approved: t
ligand name: mephenytoin
type: SyntheticOrganicLigand

meloxicam
in ch i key: ZRVUJXDFFKFLMG-UHFFFAOYSA-N
in ch i: InChI=1S/C14H13N3O4S2/c1-8-7-15-14(22-8)16-13(19)11-12(18)9-5-3-4-6-10(9)23(20,21)17(11)2/h3-7,18H,1-2H3,(H,15,16,19)
comment: Meloxicam is a non-steroidal anti-inflammatory drug (NSAID) with analgesic and antipyretic actions.
iupac name: 4-hydroxy-2-methyl-N-(5-methyl-1,3-thiazol-2-yl)-1,1-dioxo-1$l^{6},2-benzothiazine-3-carboxamide
xref: CHEMBL599
synonym: Mobic®
synonym: UHAC-62XX
approved: t
ligand name: meloxicam
type: SyntheticOrganicLigand

meclofenamic acid
canonical SMILES: OC(=O)c1ccccc1Nc1c(Cl)ccc(c1Cl)C
isomeric SMILES: OC(=O)c1ccccc1Nc1c(Cl)ccc(c1Cl)C
in ch i key: SBDNJUWAMKYJOX-UHFFFAOYSA-N
in ch i: InChI=1S/C14H11Cl2NO2/c1-8-6-7-10(15)13(12(8)16)17-11-5-3-2-4-9(11)14(18)19/h2-7,17H,1H3,(H,18,19)
comment: Meclofenamic acid is a non-steroidal anti-inflammatory drug (NSAID).
iupac name: 2-[(2,6-dichloro-3-methylphenyl)amino]benzoic acid
xref: CHEMBL509
synonym: Arquel
synonym: Movens
synonym: Meclodium
synonym: Meclophenamic Acid
synonym: Meclofenamate Sodium
synonym: Meclomen®
synonym: INF-4668
synonym: CL-583
approved: t
ligand name: meclofenamic acid
type: SyntheticOrganicLigand

mechlorethamine
canonical SMILES: ClCCN(CCCl)C
isomeric SMILES: ClCCN(CCCl)C
in ch i key: HAWPXGHAZFHHAD-UHFFFAOYSA-N
in ch i: InChI=1S/C5H11Cl2N/c1-8(4-2-6)5-3-7/h2-5H2,1H3
comment: Mechlorethamine is a nitrogen mustard and is the prototype alkylating anticancer chemotherapeutic. In addition, mechlorethamine is used in the synthesis of the opioid analgesic <Ligand id=7221/>.
iupac name: bis(2-chloroethyl)(methyl)amine
xref: CHEMBL427
synonym: Ledaga®
synonym: nitrogen mustard N-oxide hydrochloride
synonym: mustine
synonym: nitrogen mustard
synonym: Mustargen®
approved: t
ligand name: mechlorethamine
type: SyntheticOrganicLigand

loratadine
in ch i key: JCCNYMKQOSZNPW-UHFFFAOYSA-N
in ch i: InChI=1S/C22H23ClN2O2/c1-2-27-22(26)25-12-9-15(10-13-25)20-19-8-7-18(23)14-17(19)6-5-16-4-3-11-24-21(16)20/h3-4,7-8,11,14H,2,5-6,9-10,12-13H2,1H3
comment: Loratidine is an antihistamine; peripheral H1 receptor antagonist; antiallergic agent.
iupac name: ethyl 4-(8-chloro-5,6-dihydrobenzo[1,2]cyclohepta[2,4-b]pyridin-11-ylidene)piperidine-1-carboxylate
xref: CHEMBL998
synonym: Alavert
synonym: Loratadine
synonym: Claritin Reditabs
synonym: Children's Claritin
synonym: Loratadine Redidose
synonym: Claritin Hives Relief
synonym: Claritin Hives Relief Reditab
synonym: Claritin®
synonym: SCH-29851
approved: t
ligand name: loratadine
type: SyntheticOrganicLigand

loperamide
in ch i key: RDOIQAHITMMDAJ-UHFFFAOYSA-N
in ch i: InChI=1S/C29H33ClN2O2/c1-31(2)27(33)29(24-9-5-3-6-10-24,25-11-7-4-8-12-25)19-22-32-20-17-28(34,18-21-32)23-13-15-26(30)16-14-23/h3-16,34H,17-22H2,1-2H3
comment: Loperamide is an opioid-receptor agonist used as an anti-diarrheal agent. Although unreported previously, recent clinical cases of severe cardiotoxicity (and death) due to high-dose loperamide abuse have been reported <Reference id=31244/><Reference id=31245/>.
iupac name: 4-[4-(4-chlorophenyl)-4-hydroxypiperidin-1-yl]-N,N-dimethyl-2,2-diphenylbutanamide
xref: CHEMBL841
synonym: Brek
synonym: Tebloc
synonym: Imodium A-D
synonym: Imodium Advanced
synonym: Imodium A-D Ez Chews
synonym: Imodium®
synonym: R-18553
synonym: Fortasec®
synonym: Lopex
synonym: Dimor
approved: t
ligand name: loperamide
type: SyntheticOrganicLigand

lomustine
canonical SMILES: ClCCN(C(=NC1CCCCC1)O)N=O
isomeric SMILES: ClCCN(C(=NC1CCCCC1)O)N=O
in ch i key: GQYIWUVLTXOXAJ-UHFFFAOYSA-N
in ch i: InChI=1S/C9H16ClN3O2/c10-6-7-13(12-15)9(14)11-8-4-2-1-3-5-8/h8H,1-7H2,(H,11,14)
comment: Lomustine is an antineoplastic DNA alkylating agent.
iupac name: 2-chloro-N-(cyclohexyl-C-hydroxycarbonimidoyl)-N-nitrosoethan-1-amine
xref: CHEMBL514
synonym: CCNU
synonym: CeeNU®
approved: t
ligand name: lomustine
type: SyntheticOrganicLigand

lisdexamfetamine
canonical SMILES: NCCCCC(C(=NC(Cc1ccccc1)C)O)N
isomeric SMILES: NCCCC[C@@H](C(=N[C@H](Cc1ccccc1)C)O)N
in ch i key: VOBHXZCDAVEXEY-JSGCOSHPSA-N
in ch i: InChI=1S/C15H25N3O/c1-12(11-13-7-3-2-4-8-13)18-15(19)14(17)9-5-6-10-16/h2-4,7-8,12,14H,5-6,9-11,16-17H2,1H3,(H,18,19)/t12-,14-/m0/s1
comment: This drug is a prodrug of dexamphetamine. The amphetamine is released more slowly from this prodrug than by administering active amphetamine directly.
iupac name: (2S)-2,6-diamino-N-[(2S)-1-phenylpropan-2-yl]hexanimidic acid
xref: CHEMBL1201222
synonym: NRP104
synonym: Vyvanse®
approved: t
ligand name: lisdexamfetamine
type: SyntheticOrganicLigand

levomethadyl acetate
in ch i key: XBMIVRRWGCYBTQ-AVRDEDQJSA-N
in ch i: InChI=1S/C23H31NO2/c1-6-22(26-19(3)25)23(17-18(2)24(4)5,20-13-9-7-10-14-20)21-15-11-8-12-16-21/h7-16,18,22H,6,17H2,1-5H3/t18-,22-/m0/s1
comment: Levomethadyl is a opioid analgesic.
iupac name: (3S,6S)-6-(dimethylamino)-4,4-diphenylheptan-3-yl acetate
xref: CHEMBL1514
synonym: MK-790
synonym: Orlaam®
approved: t
ligand name: levomethadyl acetate
type: SyntheticOrganicLigand

levobupivacaine
canonical SMILES: CCCCN1CCCCC1C(=Nc1c(C)cccc1C)O
isomeric SMILES: CCCCN1CCCC[C@H]1C(=Nc1c(C)cccc1C)O
in ch i key: LEBVLXFERQHONN-INIZCTEOSA-N
in ch i: InChI=1S/C18H28N2O/c1-4-5-12-20-13-7-6-11-16(20)18(21)19-17-14(2)9-8-10-15(17)3/h8-10,16H,4-7,11-13H2,1-3H3,(H,19,21)/t16-/m0/s1
comment: This drug is the (S)-enantiomer of <Ligand id=2397/>.
iupac name: (2S)-1-butyl-N-(2,6-dimethylphenyl)piperidine-2-carboximidic acid
xref: CHEMBL1201193
synonym: Chirocaine®
synonym: levobupivacaine hydrochloride
approved: t
ligand name: levobupivacaine
type: SyntheticOrganicLigand

levamisole
canonical SMILES: C1CN2C(=NC(C2)c2ccccc2)S1
isomeric SMILES: C1CN2C(=N[C@H](C2)c2ccccc2)S1
in ch i key: HLFSDGLLUJUHTE-SNVBAGLBSA-N
in ch i: InChI=1S/C11H12N2S/c1-2-4-9(5-3-1)10-8-13-6-7-14-11(13)12-10/h1-5,10H,6-8H2/t10-/m1/s1
comment: Levamisole is the levorotatory isomer of tetramisole (PubChem CID 3913). This drug was originally used to treat intestinal worm infestations, but also found use in cancer treatment due to its antineoplastic action. This drug is not currently in clinical use in the US or Canada.
iupac name: (6S)-6-phenyl-2H,3H,5H,6H-imidazo[2,1-b][1,3]thiazole
xref: CHEMBL1454
synonym: Indicol
synonym: Levicon
synonym: Nilverm
synonym: Totalon
synonym: Levasole
synonym: Ripercol
synonym: Telskoot
synonym: Tramisol
synonym: Verban-H
synonym: Spartakon
synonym: Ergamisole
synonym: Tetramisole
synonym: Ergamisol®
synonym: R-12564
approved: t
ligand name: levamisole
type: SyntheticOrganicLigand

levallorphan
canonical SMILES: C=CCN1CCC23C(C1Cc1c3cc(cc1)O)CCCC2
in ch i key: OZYUPQUCAUTOBP-QXAKKESOSA-N
in ch i: InChI=1S/C19H25NO/c1-2-10-20-11-9-19-8-4-3-5-16(19)18(20)12-14-6-7-15(21)13-17(14)19/h2,6-7,13,16,18,21H,1,3-5,8-12H2/t16-,18+,19+/m0/s1
comment: Levallorphan is a morphinan class opioid receptor modulator.
xref: CHEMBL1254682
synonym: Lorfan®
synonym: Naloxiphan®
approved: t
ligand name: levallorphan
type: SyntheticOrganicLigand

lansoprazole
in ch i key: MJIHNNLFOKEZEW-UHFFFAOYSA-N
comment: Lansoprazole is a proton pump inhibitor drug. The approved drug is a racemic mixture of chemical enantiomers; (S)-lansoprazole and <Ligand id=5487/>. We show the non-stereoisomeric molecule to represent this mixture.
iupac name: 2-{[3-methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]methanesulfinyl}-1H-1,3-benzodiazole
xref: CHEMBL480
synonym: AG-1749
synonym: A-65006
synonym: Prevacid iv
synonym: Prevacid 24hr
synonym: Prevacid Solutab
synonym: Prevacid Delayed Release
synonym: Prevacid®
approved: t
ligand name: lansoprazole
type: SyntheticOrganicLigand

labetalol
canonical SMILES: CC(CCc1ccccc1)NCC(c1ccc(c(c1)C(=N)O)O)O
isomeric SMILES: CC(CCc1ccccc1)NCC(c1ccc(c(c1)C(=N)O)O)O
in ch i key: SGUAFYQXFOLMHL-UHFFFAOYSA-N
in ch i: InChI=1S/C19H24N2O3/c1-13(7-8-14-5-3-2-4-6-14)21-12-18(23)15-9-10-17(22)16(11-15)19(20)24/h2-6,9-11,13,18,21-23H,7-8,12H2,1H3,(H2,20,24)
comment: Marketed formulations may contain labetalol hydrochloride (PubChem CID 71412).
iupac name: 2-hydroxy-5-{1-hydroxy-2-[(4-phenylbutan-2-yl)amino]ethyl}benzene-1-carboximidic acid
xref: CHEMBL429
synonym: AH-5158A
synonym: SCH-15719W
synonym: Normodyne®
synonym: Trandate®
approved: t
ligand name: labetalol
type: SyntheticOrganicLigand

ketotifen
canonical SMILES: CN1CCC(=C2c3ccccc3CC(=O)c3c2ccs3)CC1
isomeric SMILES: CN1CCC(=C2c3ccccc3CC(=O)c3c2ccs3)CC1
in ch i key: ZCVMWBYGMWKGHF-UHFFFAOYSA-N
in ch i: InChI=1S/C19H19NOS/c1-20-9-6-13(7-10-20)18-15-5-3-2-4-14(15)12-17(21)19-16(18)8-11-22-19/h2-5,8,11H,6-7,9-10,12H2,1H3
comment: Ketotifen is an antihistamine. This drug may be used in eye drop or oral formulations, where the active ingredient is ketotifen fumarate (PubChem CID 5282408).
iupac name: 10-(1-methylpiperidin-4-ylidene)-5H-benzo[1,2]cyclohepta[3,4-b]thiophen-4-one
xref: CHEMBL534
synonym: HC-20511
synonym: laway
synonym: Zaditor®
approved: t
ligand name: ketotifen
type: SyntheticOrganicLigand

isoetarine
canonical SMILES: CCC(C(c1ccc(c(c1)O)O)O)NC(C)C
isomeric SMILES: CCC(C(c1ccc(c(c1)O)O)O)NC(C)C
in ch i key: HUYWAWARQUIQLE-UHFFFAOYSA-N
in ch i: InChI=1S/C13H21NO3/c1-4-10(14-8(2)3)13(17)9-5-6-11(15)12(16)7-9/h5-8,10,13-17H,4H2,1-3H3
comment: Isoetharine is a bronchodilator. Note that the US FDA approved drug is isoetharine.
iupac name: 4-{1-hydroxy-2-[(propan-2-yl)amino]butyl}benzene-1,2-diol
xref: CHEMBL1201213
synonym: Numotac
synonym: Isoetarine
synonym: Isoetharine Mesylate
synonym: Isoetharine Hydrochloride
synonym: Isoetharine Hydrochloride S/F
synonym: Bronkosol®
synonym: Bronkometer®
synonym: WIN-3406
approved: t
ligand name: isoetarine
type: SyntheticOrganicLigand

isocarboxazid
canonical SMILES: Cc1onc(c1)C(=O)NNCc1ccccc1
isomeric SMILES: Cc1onc(c1)C(=O)NNCc1ccccc1
in ch i key: XKFPYPQQHFEXRZ-UHFFFAOYSA-N
in ch i: InChI=1S/C12H13N3O2/c1-9-7-11(15-17-9)12(16)14-13-8-10-5-3-2-4-6-10/h2-7,13H,8H2,1H3,(H,14,16)
comment: Isocarboxazid is a monoamine oxidase inhibitor (MAOI).
iupac name: N'-benzyl-5-methyl-1,2-oxazole-3-carbohydrazide
xref: CHEMBL1201168
synonym: Marplan®
synonym: Enerzer
synonym: Marplon
approved: t
ligand name: isocarboxazid
type: SyntheticOrganicLigand

indapamide
in ch i key: NDDAHWYSQHTHNT-UHFFFAOYSA-N
comment: Indapamide is a thiazide diuretic drug.
iupac name: 4-chloro-N-(2-methyl-2,3-dihydroindol-1-yl)-3-sulfamoylbenzamide
xref: CHEMBL406
synonym: Lozol®
synonym: Hypen SR®
synonym: Natrilix
synonym: Insig
approved: t
ligand name: indapamide
type: SyntheticOrganicLigand

inamrinone
canonical SMILES: Oc1ncc(cc1N)c1ccncc1
isomeric SMILES: Oc1ncc(cc1N)c1ccncc1
in ch i key: RNLQIBCLLYYYFJ-UHFFFAOYSA-N
in ch i: InChI=1S/C10H9N3O/c11-9-5-8(6-13-10(9)14)7-1-3-12-4-2-7/h1-6H,11H2,(H,13,14)
comment: Inamrinone is a phosphodiesterase inhibitor. Marketed formulations may contain inamrinone lactate (PubChem CID 3035194).
iupac name: 3-amino-5-(pyridin-4-yl)pyridin-2-ol
xref: CHEMBL12856
synonym: Inocor®
synonym: amrinone lactate
synonym: WIN-40680
approved: t
ligand name: inamrinone
type: SyntheticOrganicLigand

ifosfamide
canonical SMILES: ClCCNP1(=O)OCCCN1CCCl
isomeric SMILES: ClCCNP1(=O)OCCCN1CCCl
in ch i key: HOMGKSMUEGBAAB-UHFFFAOYSA-N
comment: Ifosfamide is a DNA alkylating drug, and has additional immunosuppressant action. Ifosfamide is biologically inactive. In vivo metabolism is necessary to generate the active substance, isophosphamide mustard (IPM; PubChem CID 100427) <Reference id=29206/>.
iupac name: 3-(2-chloroethyl)-2-[(2-chloroethyl)amino]-1,3,2λ5-oxazaphosphinan-2-one
xref: CHEMBL1024
synonym: Holoxan®
synonym: Ifosfamide
synonym: Ifsofamide
synonym: Ifex®
synonym: MJF-9325
synonym: Z-4942
approved: t
ligand name: ifosfamide
type: SyntheticOrganicLigand

ibutilide
in ch i key: ALOBUEHUHMBRLE-UHFFFAOYSA-N
in ch i: InChI=1S/C20H36N2O3S/c1-4-6-7-8-9-16-22(5-2)17-10-11-20(23)18-12-14-19(15-13-18)21-26(3,24)25/h12-15,20-21,23H,4-11,16-17H2,1-3H3
comment: Ibutilide is an antiarrhythmic drug. Marketed formulations may contain ibutilide fumarate (PubChem CID 6437366).
iupac name: N-(4-{4-[ethyl(heptyl)amino]-1-hydroxybutyl}phenyl)methanesulfonamide
xref: CHEMBL533
synonym: Corvert®
synonym: U-70226E
approved: t
ligand name: ibutilide
type: SyntheticOrganicLigand

hydroxyzine
canonical SMILES: OCCOCCN1CCN(CC1)C(c1ccc(cc1)Cl)c1ccccc1
isomeric SMILES: OCCOCCN1CCN(CC1)C(c1ccc(cc1)Cl)c1ccccc1
in ch i key: ZQDWXGKKHFNSQK-UHFFFAOYSA-N
in ch i: InChI=1S/C21H27ClN2O2/c22-20-8-6-19(7-9-20)21(18-4-2-1-3-5-18)24-12-10-23(11-13-24)14-16-26-17-15-25/h1-9,21,25H,10-17H2
comment: Hydroxyzine is a first-generation diphenylmethane and piperazine class antihistamine. Second-generation antihistamine <Ligand id=1222/> is one of the metabolites of hydroxyzine, but cetirizine differs in that it appears not to cross the blood-brain barrier to any significant level.
iupac name: 2-(2-{4-[(4-chlorophenyl)(phenyl)methyl]piperazin-1-yl}ethoxy)ethan-1-ol
xref: CHEMBL896
synonym: Orgatrax
synonym: Hy-Pam %2225%22
synonym: Hydroxyzine
synonym: Vistaril®
synonym: Atarax®
synonym: hydroxyzine hydrochloride
synonym: hydroxyzine pamoate
approved: t
ligand name: hydroxyzine
type: SyntheticOrganicLigand

hydroxychloroquine
canonical SMILES: OCCN(CCCC(Nc1ccnc2c1ccc(c2)Cl)C)CC
isomeric SMILES: OCCN(CCCC(Nc1ccnc2c1ccc(c2)Cl)C)CC
in ch i key: XXSMGPRMXLTPCZ-UHFFFAOYSA-N
in ch i: InChI=1S/C18H26ClN3O/c1-3-22(11-12-23)10-4-5-14(2)21-17-8-9-20-18-13-15(19)6-7-16(17)18/h6-9,13-14,23H,3-5,10-12H2,1-2H3,(H,20,21)
comment: Hydroxychloroquine (HCQ) is a 4-aminoquinoline and used primarily as an antimalarial drug. The approved drug is a racemic mixture and we show the chemical structure without stereochemistry to represent the mixture. The non-isomeric structure is also represented in the PubChem, ChEMBL and ChEBI entries listed in the links table below, while the two enantiomers forming the racemate are represented by PubChem CID 178395 and PubChem CID 178396. The marketed formulations contain hydroxychloroquine sulfate (PubChem CID 3044369). Activity at non-malarial protein targets: Although this drug has direct effects on survival of the malaria parasite it also appears to be an antagonist of two of the human TOLL-like receptors (TLR7 and TLR9). Antagonism of these receptors is likely related to the anti-inflammatory action of this drug in auto-immune diseases. Some patients with systemic lupus erythematosus (SLE) and rheumatoid arthritis are prescribed HCQ <Reference id=40133/>. Activity against SARS-CoV-2: Hydroxychloroquine exhibits in vitro antiviral activity against both the original SARS coronavirus (SARS-CoV) <Reference id=38969/> and SARS-CoV-2 which emerged in 2019 <Reference id=38970/>. Extreme caution must be taken when condisering using hydroxychloroquine (HCQ) as it has severe cardiac adverse effects, and in addition its distribution to lung tissue is unknown. There was much hype around repositioning HCQ to treat COVID-19. But this was based on preliminary evidence from a cohort of COVID-19 patients in a VERY small study <Reference id=40131/> and anecdotal evidence that patients taking HCQ for other diseases fared better if they developed COVID-19. There was also a lot of controversy around some of the larger scale trials, particularly of how they were carried out, and/or how they were reported or published. Results from subsequent well run, well powered, large scale RCTs does not support any clinical benefit from HCQ in COVID-19 patients. HCQ may even pose an acceptable…
iupac name: 2-({4-[(7-chloroquinolin-4-yl)amino]pentyl}(ethyl)amino)ethan-1-ol
xref: CHEMBL1535
synonym: Quensyl
synonym: Ercoquin
synonym: Oxichlorochine
synonym: Hydroxychloroquine Sulfate
synonym: Plaquenil®
synonym: Dolquine®
approved: t
ligand name: hydroxychloroquine
type: SyntheticOrganicLigand

hydroflumethiazide
in ch i key: DMDGGSIALPNSEE-UHFFFAOYSA-N
in ch i: InChI=1S/C8H8F3N3O4S2/c9-8(10,11)4-1-5-7(2-6(4)19(12,15)16)20(17,18)14-3-13-5/h1-2,13-14H,3H2,(H2,12,15,16)
comment: Hydroflumethiazide is a diuretic.
iupac name: 1,1-dioxo-6-(trifluoromethyl)-3,4-dihydro-2H-benzo[e][1,2,4]thiadiazine-7-sulfonamide
xref: CHEMBL1763
synonym: Diucardin
synonym: Hydroflumethiazide
synonym: Saluron®
approved: t
ligand name: hydroflumethiazide
type: SyntheticOrganicLigand

hexylcaine
canonical SMILES: CC(OC(=O)c1ccccc1)CNC1CCCCC1
isomeric SMILES: CC(OC(=O)c1ccccc1)CNC1CCCCC1
in ch i key: DKLKMKYDWHYZTD-UHFFFAOYSA-N
in ch i: InChI=1S/C16H23NO2/c1-13(12-17-15-10-6-3-7-11-15)19-16(18)14-8-4-2-5-9-14/h2,4-5,8-9,13,15,17H,3,6-7,10-12H2,1H3
comment: Hexylcaine is a short-acting local anaesthetic.
iupac name: 1-(cyclohexylamino)propan-2-yl benzoate
xref: CHEMBL1197
synonym: Cyclaine®
synonym: osmocaine
approved: t
ligand name: hexylcaine
type: SyntheticOrganicLigand

guanethidine
canonical SMILES: NC(=N)NCCN1CCCCCCC1
isomeric SMILES: NC(=N)NCCN1CCCCCCC1
in ch i key: ACGDKVXYNVEAGU-UHFFFAOYSA-N
in ch i: InChI=1S/C10H22N4/c11-10(12)13-6-9-14-7-4-2-1-3-5-8-14/h1-9H2,(H4,11,12,13)
comment: Marketed formulations may contain guanethidine monosulfate (PubChem CID 86471).
iupac name: 1-[2-(azocan-1-yl)ethyl]guanidine
xref: CHEMBL765
synonym: Ismelin®
synonym: SU-5864
approved: t
ligand name: guanethidine
type: SyntheticOrganicLigand

guanadrel
canonical SMILES: NC(=N)NCC1COC2(O1)CCCCC2
isomeric SMILES: NC(=N)NCC1COC2(O1)CCCCC2
in ch i key: HPBNRIOWIXYZFK-UHFFFAOYSA-N
in ch i: InChI=1S/C10H19N3O2/c11-9(12)13-6-8-7-14-10(15-8)4-2-1-3-5-10/h8H,1-7H2,(H4,11,12,13)
comment: Guanadrel is a postganglionic adrenergic blocking drug.
iupac name: 1-{1,4-dioxaspiro[4.5]decan-2-ylmethyl}guanidine
xref: CHEMBL1037
synonym: Hylorel®
synonym: U-28288D
synonym: CL-1388R
approved: t
ligand name: guanadrel
type: SyntheticOrganicLigand

glutethimide
canonical SMILES: CCC1(CCC(=NC1=O)O)c1ccccc1
isomeric SMILES: CCC1(CCC(=NC1=O)O)c1ccccc1
in ch i key: JMBQKKAJIKAWKF-UHFFFAOYSA-N
in ch i: InChI=1S/C13H15NO2/c1-2-13(10-6-4-3-5-7-10)9-8-11(15)14-12(13)16/h3-7H,2,8-9H2,1H3,(H,14,15,16)
comment: This drug has hypnotic and sedative actions.
iupac name: 3-ethyl-6-hydroxy-3-phenyl-2,3,4,5-tetrahydropyridin-2-one
xref: CHEMBL1102
synonym: Doriden®
synonym: Elrodorm
synonym: Noxyron
synonym: Glimid
approved: t
ligand name: glutethimide
type: SyntheticOrganicLigand

frovatriptan
canonical SMILES: CNC1Cc2c(CC1)[nH]c1c2cc(cc1)C(=N)O
isomeric SMILES: CN[C@H]1Cc2c(CC1)[nH]c1c2cc(cc1)C(=N)O
in ch i key: XPSQPHWEGNHMSK-SECBINFHSA-N
in ch i: InChI=1S/C14H17N3O/c1-16-9-3-5-13-11(7-9)10-6-8(14(15)18)2-4-12(10)17-13/h2,4,6,9,16-17H,3,5,7H2,1H3,(H2,15,18)/t9-/m1/s1
comment: Frovatriptan is a triptan (tryptamine-based) drug.
iupac name: (3R)-3-(methylamino)-2,3,4,9-tetrahydro-1H-carbazole-6-carboximidic acid
xref: CHEMBL1279
synonym: Frova®
synonym: SB-209509-AX
synonym: VML-251
approved: t
ligand name: frovatriptan
type: SyntheticOrganicLigand

fosphenytoin
in ch i key: XWLUWCNOOVRFPX-UHFFFAOYSA-N
in ch i: InChI=1S/C16H15N2O6P/c19-14-16(12-7-3-1-4-8-12,13-9-5-2-6-10-13)17-15(20)18(14)11-24-25(21,22)23/h1-10H,11H2,(H,17,20)(H2,21,22,23)
comment: Fosphenytoin is a prodrug of phenytoin. This drug is an anticonvulsant. Marketed formulations may contain fosphenytoin sodium (PubChem CID 56338).
iupac name: [(2-hydroxy-5-oxo-4,4-diphenyl-4,5-dihydro-1H-imidazol-1-yl)methoxy]phosphonic acid
xref: CHEMBL1201336
synonym: CI-982
synonym: ACC-9653-010
synonym: Cerebyx®
synonym: Sesquient®
approved: t
ligand name: fosphenytoin
type: SyntheticOrganicLigand

fluvoxamine
canonical SMILES: NCCO/N=C(/c1ccc(cc1)C(F)(F)F)/CCCCOC
isomeric SMILES: NCCO/N=C(/c1ccc(cc1)C(F)(F)F)/CCCCOC
in ch i key: CJOFXWAVKWHTFT-XSFVSMFZSA-N
in ch i: InChI=1S/C15H21F3N2O2/c1-21-10-3-2-4-14(20-22-11-9-19)12-5-7-13(8-6-12)15(16,17)18/h5-8H,2-4,9-11,19H2,1H3/b20-14+
comment: Fluvoxamine is an antidepressant belonging to the selective serotonin reuptake inhibitor (SSRI) drug group. Marketed formulations may contain fluvoxamine maleate (PubChem CID 9560989). SARS-CoV-2 and COVID-19: Evidence that is emerging from randomised, placebo-controlled clinical trials <Reference id=43142/> suggests that fluvoxamine may offer potential as a therapuetic for non-hospitalised COVID-19 patients. Multiple fluvoxamine mechanisms of action may be at play <Reference id=43141/>, and much remains to clarified about the patients who would benefit most, efficacy in infections with different SARS-CoV-2 variants, and whether fluvoxamine's effect occurs in addition to the benefit demonstrated by other therapies.
xref: CHEMBL814
synonym: Luvox cr
synonym: Luvox®
synonym: U-23000
synonym: Floxyfral
synonym: Fevarin
approved: t
ligand name: fluvoxamine
type: SyntheticOrganicLigand

flavoxate
in ch i key: SPIUTQOUKAMGCX-UHFFFAOYSA-N
in ch i: InChI=1S/C24H25NO4/c1-17-21(26)19-11-8-12-20(23(19)29-22(17)18-9-4-2-5-10-18)24(27)28-16-15-25-13-6-3-7-14-25/h2,4-5,8-12H,3,6-7,13-16H2,1H3
comment: Marketed formulations may contain flavoxate hydrochloride (PubChem CID 441345).
iupac name: 2-(piperidin-1-yl)ethyl 3-methyl-4-oxo-2-phenyl-4H-chromene-8-carboxylate
xref: CHEMBL1493
synonym: Urispas®
synonym: W-61
synonym: Genurin
synonym: Uritac
synonym: Bladderon
synonym: Bladuril
approved: t
ligand name: flavoxate
type: SyntheticOrganicLigand

fenofibrate
in ch i key: YMTINGFKWWXKFG-UHFFFAOYSA-N
in ch i: InChI=1S/C20H21ClO4/c1-13(2)24-19(23)20(3,4)25-17-11-7-15(8-12-17)18(22)14-5-9-16(21)10-6-14/h5-13H,1-4H3
comment: Fenofibrate is an antilipemic agent. Combination drug formulations often contain statins.
iupac name: propan-2-yl 2-[4-(4-chlorobenzoyl)phenoxy]-2-methylpropanoate
xref: CHEMBL672
synonym: ABT-335
synonym: Lipantil®
synonym: Supralip®
synonym: Antara
synonym: Lipidil
synonym: Lipofen
synonym: Triglide
synonym: Fenoglide
synonym: Fenofibrate
synonym: Tricor®
approved: t
ligand name: fenofibrate
type: SyntheticOrganicLigand

etodolac
canonical SMILES: CCC1(OCCc2c1[nH]c1c2cccc1CC)CC(=O)O
isomeric SMILES: CCC1(OCCc2c1[nH]c1c2cccc1CC)CC(=O)O
in ch i key: NNYBQONXHNTVIJ-UHFFFAOYSA-N
in ch i: InChI=1S/C17H21NO3/c1-3-11-6-5-7-12-13-8-9-21-17(4-2,10-14(19)20)16(13)18-15(11)12/h5-7,18H,3-4,8-10H2,1-2H3,(H,19,20)
comment: Etodolac is a nonsteroidal anti-inflammatory drug (NSAID).
iupac name: 2-{1,8-diethyl-1H,3H,4H,9H-pyrano[3,4-b]indol-1-yl}acetic acid
xref: CHEMBL622
synonym: AY-24236
synonym: Lodine Xl
synonym: Lodine®
approved: t
ligand name: etodolac
type: SyntheticOrganicLigand

etidronic acid
canonical SMILES: CC(P(=O)(O)O)(P(=O)(O)O)O
isomeric SMILES: CC(P(=O)(O)O)(P(=O)(O)O)O
in ch i key: DBVJJBKOTRCVKF-UHFFFAOYSA-N
in ch i: InChI=1S/C2H8O7P2/c1-2(3,10(4,5)6)11(7,8)9/h3H,1H3,(H2,4,5,6)(H2,7,8,9)
comment: Etidronic acid is a bisphosphonate drug.
iupac name: (1-hydroxy-1-phosphonoethyl)phosphonic acid
xref: CHEMBL871
synonym: Didronel®
synonym: etidronate disodium
approved: t
ligand name: etidronic acid
type: SyntheticOrganicLigand

ethotoin
canonical SMILES: CCN1C(=O)C(N=C1O)c1ccccc1
isomeric SMILES: CCN1C(=O)C(N=C1O)c1ccccc1
in ch i key: SZQIFWWUIBRPBZ-UHFFFAOYSA-N
in ch i: InChI=1S/C11H12N2O2/c1-2-13-10(14)9(12-11(13)15)8-6-4-3-5-7-8/h3-7,9H,2H2,1H3,(H,12,15)
comment: Ethotoin is an anticonvulsant drug.
iupac name: 1-ethyl-2-hydroxy-4-phenyl-4,5-dihydro-1H-imidazol-5-one
xref: CHEMBL1095
synonym: Peganone®
approved: t
ligand name: ethotoin
type: SyntheticOrganicLigand

ethosuximide
canonical SMILES: CC1(CC)CC(=NC1=O)O
isomeric SMILES: CC1(CC)CC(=NC1=O)O
in ch i key: HAPOVYFOVVWLRS-UHFFFAOYSA-N
in ch i: InChI=1S/C7H11NO2/c1-3-7(2)4-5(9)8-6(7)10/h3-4H2,1-2H3,(H,8,9,10)
comment: Ethosuximide is a succinimide anticonvulsant. It is often preferred over <Ligand id=7009/> as it does not produce the same hepatotoxicity.
iupac name: 3-ethyl-5-hydroxy-3-methyl-3,4-dihydro-2H-pyrrol-2-one
xref: CHEMBL696
synonym: CN-10395
synonym: PM-671
synonym: CI-366
synonym: Zarontin®
approved: t
ligand name: ethosuximide
type: SyntheticOrganicLigand

ethopropazine
canonical SMILES: CCN(C(CN1c2ccccc2Sc2c1cccc2)C)CC
isomeric SMILES: CCN(C(CN1c2ccccc2Sc2c1cccc2)C)CC
in ch i key: CDOZDBSBBXSXLB-UHFFFAOYSA-N
in ch i: InChI=1S/C19H24N2S/c1-4-20(5-2)15(3)14-21-16-10-6-8-12-18(16)22-19-13-9-7-11-17(19)21/h6-13,15H,4-5,14H2,1-3H3
comment: Ethopropazine is a phenothiazine derivative drug.
iupac name: diethyl[1-(10H-phenothiazin-10-yl)propan-2-yl]amine
xref: CHEMBL1206
synonym: Parsidol®
approved: t
ligand name: ethopropazine
type: SyntheticOrganicLigand

ethchlorvynol
canonical SMILES: CCC(C#C)(C=CCl)O
isomeric SMILES: CCC(C#C)(/C=C/Cl)O
in ch i key: ZEHYJZXQEQOSON-AATRIKPKSA-N
in ch i: InChI=1S/C7H9ClO/c1-3-7(9,4-2)5-6-8/h1,5-6,9H,4H2,2H3/b6-5+
comment: Ethchlorvynol's use has largely been replaced by safer alternative hypnotics.
iupac name: (1E)-1-chloro-3-ethylpent-1-en-4-yn-3-ol
xref: CHEMBL591
synonym: Placidyl®
approved: t
ligand name: ethchlorvynol
type: SyntheticOrganicLigand

desloratadine
canonical SMILES: Clc1ccc2c(c1)CCc1c(C2=C2CCNCC2)nccc1
isomeric SMILES: Clc1ccc2c(c1)CCc1c(C2=C2CCNCC2)nccc1
in ch i key: JAUOIFJMECXRGI-UHFFFAOYSA-N
in ch i: InChI=1S/C19H19ClN2/c20-16-5-6-17-15(12-16)4-3-14-2-1-9-22-19(14)18(17)13-7-10-21-11-8-13/h1-2,5-6,9,12,21H,3-4,7-8,10-11H2
comment: Desloratadine is a tricyclic H1-antihistamine. It is the major metabolite of <Ligand id=7216/>.
iupac name: 8-chloro-11-piperidin-4-ylidene-5,6-dihydrobenzo[1,2]cyclohepta[2,4-b]pyridine
xref: CHEMBL1172
synonym: Desloratadine
synonym: Clarinex®
synonym: SCH-34117
approved: t
ligand name: desloratadine
type: SyntheticOrganicLigand

halazepam
in ch i key: WYCLKVQLVUQKNZ-UHFFFAOYSA-N
comment: Halazepam is benzodiazepine drug.
iupac name: 7-chloro-5-phenyl-1-(2,2,2-trifluoroethyl)-2,3-dihydro-1H-1,4-benzodiazepin-2-one
xref: CHEMBL970
synonym: Paxipam
synonym: SCH-12041
synonym: Alapryl®
synonym: Pacinone
approved: t
ligand name: halazepam
type: SyntheticOrganicLigand

escitalopram
canonical SMILES: N#Cc1ccc2c(c1)COC2(CCCN(C)C)c1ccc(cc1)F
in ch i key: WSEQXVZVJXJVFP-FQEVSTJZSA-N
in ch i: InChI=1S/C20H21FN2O/c1-23(2)11-3-10-20(17-5-7-18(21)8-6-17)19-9-4-15(13-22)12-16(19)14-24-20/h4-9,12H,3,10-11,14H2,1-2H3/t20-/m0/s1
comment: Escitalopram is a selective serotonin-reuptake inhibitor (SSRI) drug. It is the S-enantiomer of <Ligand id=7547/>. Marketed formulations may contain escitalopram oxalate (PubChem CID 146571). An X-ray structure of SERT bound by escitalopram ((S)-citalopram) reveals two binding sites for the drug: one central site, and one allosteric site <Reference id=30922/>. When (S)-citalopram binds the allosteric site, it prevents unbinding of ligand at the central site, thereby preventing further ligand transport.
iupac name: (1S)-1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-2-benzofuran-5-carbonitrile
xref: CHEMBL1508
synonym: LU-26-054-0
synonym: Lexapro®
synonym: Cipralex®
approved: t
ligand name: escitalopram
type: SyntheticOrganicLigand

epinastine
canonical SMILES: N=C1NCC2N1c1ccccc1Cc1c2cccc1
isomeric SMILES: N=C1NCC2N1c1ccccc1Cc1c2cccc1
in ch i key: WHWZLSFABNNENI-UHFFFAOYSA-N
in ch i: InChI=1S/C16H15N3/c17-16-18-10-15-13-7-3-1-5-11(13)9-12-6-2-4-8-14(12)19(15)16/h1-8,15H,9-10H2,(H2,17,18)
comment: Epinastine is an antihistamine.
xref: CHEMBL1106
synonym: Elestat®
synonym: epinastine hydrochloride
approved: t
ligand name: epinastine
type: SyntheticOrganicLigand

enflurane
canonical SMILES: FC(OC(C(Cl)F)(F)F)F
isomeric SMILES: FC(OC(C(Cl)F)(F)F)F
in ch i key: JPGQOUSTVILISH-UHFFFAOYSA-N
in ch i: InChI=1S/C3H2ClF5O/c4-1(5)3(8,9)10-2(6)7/h1-2H
comment: Enflurane is a halogenated ether inhalational anaesthetic, but it is no longer in common use. It is a structural isomer of <Ligand id=2505/>.
iupac name: 2-chloro-1-(difluoromethoxy)-1,1,2-trifluoroethane
xref: CHEMBL1257
synonym: Ethrane®
synonym: Forane®
approved: t
ligand name: enflurane
type: SyntheticOrganicLigand

emedastine
canonical SMILES: CCOCCn1c(nc2c1cccc2)N1CCCN(CC1)C
isomeric SMILES: CCOCCn1c(nc2c1cccc2)N1CCCN(CC1)C
in ch i key: KBUZBQVCBVDWKX-UHFFFAOYSA-N
in ch i: InChI=1S/C17H26N4O/c1-3-22-14-13-21-16-8-5-4-7-15(16)18-17(21)20-10-6-9-19(2)11-12-20/h4-5,7-8H,3,6,9-14H2,1-2H3
comment: Emedastine is an antihistamine.
iupac name: 1-(2-ethoxyethyl)-2-(4-methyl-1,4-diazepan-1-yl)-1H-1,3-benzodiazole
xref: CHEMBL594
synonym: AL-3432A
synonym: Emadine®
approved: t
ligand name: emedastine
type: SyntheticOrganicLigand

dyclonine
canonical SMILES: CCCCOc1ccc(cc1)C(=O)CCN1CCCCC1
isomeric SMILES: CCCCOc1ccc(cc1)C(=O)CCN1CCCCC1
in ch i key: BZEWSEKUUPWQDQ-UHFFFAOYSA-N
in ch i: InChI=1S/C18H27NO2/c1-2-3-15-21-17-9-7-16(8-10-17)18(20)11-14-19-12-5-4-6-13-19/h7-10H,2-6,11-15H2,1H3
comment: Dyclonine is a local anesthetic. Marketed formulations contain dyclonine hydrochloride (PubChem CID 68304).
iupac name: 1-(4-butoxyphenyl)-3-(piperidin-1-yl)propan-1-one
xref: CHEMBL1201217
synonym: dyclocaine
synonym: Dyclone
approved: t
ligand name: dyclonine
type: SyntheticOrganicLigand

droperidol
in ch i key: RMEDXOLNCUSCGS-UHFFFAOYSA-N
in ch i: InChI=1S/C22H22FN3O2/c23-17-9-7-16(8-10-17)21(27)6-3-13-25-14-11-18(12-15-25)26-20-5-2-1-4-19(20)24-22(26)28/h1-2,4-5,7-11H,3,6,12-15H2,(H,24,28)
comment: Droperidol has sedative, tranquilising, and anti-nausea actions.
iupac name: 1-(4-fluorophenyl)-4-[4-(2-hydroxy-1H-1,3-benzodiazol-1-yl)-1,2,3,6-tetrahydropyridin-1-yl]butan-1-one
xref: CHEMBL1108
synonym: Dridol
synonym: Droperidol
synonym: Inapsine®
synonym: Droleptan®
synonym: R-4749
synonym: McN-JR-4749
approved: t
ligand name: droperidol
type: SyntheticOrganicLigand

doxylamine
canonical SMILES: CN(CCOC(c1ccccn1)(c1ccccc1)C)C
isomeric SMILES: CN(CCOC(c1ccccn1)(c1ccccc1)C)C
in ch i key: HCFDWZZGGLSKEP-UHFFFAOYSA-N
in ch i: InChI=1S/C17H22N2O/c1-17(20-14-13-19(2)3,15-9-5-4-6-10-15)16-11-7-8-12-18-16/h4-12H,13-14H2,1-3H3
comment: Doxylamine is an antihistamine.
iupac name: dimethyl({2-[1-phenyl-1-(pyridin-2-yl)ethoxy]ethyl})amine
xref: CHEMBL1004
synonym: Decapryn
synonym: Doxy-Sleep-Aid
synonym: Doxylamine Succinate
synonym: Unisom®
approved: t
ligand name: doxylamine
type: SyntheticOrganicLigand

doxazosin
in ch i key: RUZYUOTYCVRMRZ-UHFFFAOYSA-N
in ch i: InChI=1S/C23H25N5O5/c1-30-18-11-14-15(12-19(18)31-2)25-23(26-21(14)24)28-9-7-27(8-10-28)22(29)20-13-32-16-5-3-4-6-17(16)33-20/h3-6,11-12,20H,7-10,13H2,1-2H3,(H2,24,25,26)
comment: Doxazosin blocks α1-adrenoceptors. Marketed formulations may contain doxazosin mesylate (PubChem CID 62978).
iupac name: 2-[4-(2,3-dihydro-1,4-benzodioxine-2-carbonyl)piperazin-1-yl]-6,7-dimethoxy-3,4-dihydroquinazolin-4-imine
xref: CHEMBL707
synonym: Cardura Xl
synonym: Cardura®
synonym: UK-3327427
approved: t
ligand name: doxazosin
type: SyntheticOrganicLigand

doxapram
in ch i key: XFDJYSQDBULQSI-UHFFFAOYSA-N
in ch i: InChI=1S/C24H30N2O2/c1-2-26-19-22(13-14-25-15-17-28-18-16-25)24(23(26)27,20-9-5-3-6-10-20)21-11-7-4-8-12-21/h3-12,22H,2,13-19H2,1H3
comment: Doxapram is an analeptic, ie it is a central nervous system stimulant. Marketed formulations may contain doxapram hydrochloride (PubChem CID 64647).
iupac name: 1-ethyl-4-[2-(morpholin-4-yl)ethyl]-3,3-diphenylpyrrolidin-2-one
xref: CHEMBL1754
synonym: AHR-619
synonym: Stimulexin
synonym: Dopram®
approved: t
ligand name: doxapram
type: SyntheticOrganicLigand

disulfiram
canonical SMILES: CCN(C(=S)SSC(=S)N(CC)CC)CC
isomeric SMILES: CCN(C(=S)SSC(=S)N(CC)CC)CC
in ch i key: AUZONCFQVSMFAP-UHFFFAOYSA-N
in ch i: InChI=1S/C10H20N2S4/c1-5-11(6-2)9(13)15-16-10(14)12(7-3)8-4/h5-8H2,1-4H3
comment: Disulfiram inhibits acetaldehyde dehydrogenase to expedite acetaldehyde accumulation and rapid onset (within 5-10 minutes of alcohol intake) of the unpleasant effects typical of a hangover.
xref: CHEMBL964
synonym: Antabuse®
synonym: NSC-25953
approved: t
ligand name: disulfiram
type: SyntheticOrganicLigand

disopyramide
in ch i key: UVTNFZQICZKOEM-UHFFFAOYSA-N
in ch i: InChI=1S/C21H29N3O/c1-16(2)24(17(3)4)15-13-21(20(22)25,18-10-6-5-7-11-18)19-12-8-9-14-23-19/h5-12,14,16-17H,13,15H2,1-4H3,(H2,22,25)
comment: Marketed formulations may containdisopyramide phosphate (PubChem CID 30928).
iupac name: 4-[bis(propan-2-yl)amino]-2-phenyl-2-(pyridin-2-yl)butanimidic acid
xref: CHEMBL517
synonym: Norpace Cr
synonym: Norpace®
synonym: Rythmodan®
synonym: SC-7031
synonym: SC-13957
approved: t
ligand name: disopyramide
type: SyntheticOrganicLigand

dipivefrine
in ch i key: OCUJLLGVOUDECM-UHFFFAOYSA-N
in ch i: InChI=1S/C19H29NO5/c1-18(2,3)16(22)24-14-9-8-12(13(21)11-20-7)10-15(14)25-17(23)19(4,5)6/h8-10,13,20-21H,11H2,1-7H3
comment: Dipivefrin is a prodrug of adrenaline/epinephrine.
iupac name: 2-[(2,2-dimethylpropanoyl)oxy]-4-[1-hydroxy-2-(methylamino)ethyl]phenyl 2,2-dimethylpropanoate
xref: CHEMBL1201262
synonym: Akpro
synonym: Dipivefrin Hydrochloride
synonym: Propine®
approved: t
ligand name: dipivefrine
type: SyntheticOrganicLigand

diphenylpyraline
canonical SMILES: CN1CCC(CC1)OC(c1ccccc1)c1ccccc1
isomeric SMILES: CN1CCC(CC1)OC(c1ccccc1)c1ccccc1
in ch i key: OWQUZNMMYNAXSL-UHFFFAOYSA-N
in ch i: InChI=1S/C19H23NO/c1-20-14-12-18(13-15-20)21-19(16-8-4-2-5-9-16)17-10-6-3-7-11-17/h2-11,18-19H,12-15H2,1H3
comment: Diphenylpyraline is a first-generation diphenylpiperidine antihistamine with anticholinergic effects.
iupac name: 4-(diphenylmethoxy)-1-methylpiperidine
xref: CHEMBL1492
synonym: Hispril®
approved: t
ligand name: diphenylpyraline
type: SyntheticOrganicLigand

diphenoxylate
in ch i key: HYPPXZBJBPSRLK-UHFFFAOYSA-N
in ch i: InChI=1S/C30H32N2O2/c1-2-34-28(33)29(25-12-6-3-7-13-25)18-21-32(22-19-29)23-20-30(24-31,26-14-8-4-9-15-26)27-16-10-5-11-17-27/h3-17H,2,18-23H2,1H3
comment: Diphenoxylate is a phenylpiperidine series, centrally-active opioid antidiarrheal drug. Diphenoxylate is metabolised in vivo to form <Ligand id=7592/>. Both diphenoxylate and difenoxin can be proescribed in fixed-dose combination with atropine to act as an abuse deterrent. Atropine causes severe weakness and nausea if standard doses are exceeded.
iupac name: ethyl 1-(3-cyano-3,3-diphenylpropyl)-4-phenylpiperidine-4-carboxylate
xref: CHEMBL1201294
synonym: Lomotil®
synonym: diphenoxylate HCl
approved: t
ligand name: diphenoxylate
type: SyntheticOrganicLigand

diphenidol
canonical SMILES: OC(c1ccccc1)(c1ccccc1)CCCN1CCCCC1
isomeric SMILES: OC(c1ccccc1)(c1ccccc1)CCCN1CCCCC1
in ch i key: OGAKLTJNUQRZJU-UHFFFAOYSA-N
in ch i: InChI=1S/C21H27NO/c23-21(19-11-4-1-5-12-19,20-13-6-2-7-14-20)15-10-18-22-16-8-3-9-17-22/h1-2,4-7,11-14,23H,3,8-10,15-18H2
comment: Diphenidol is a muscarinic antagonist , antiemetic and antivertigo drug.
iupac name: 1,1-diphenyl-4-(piperidin-1-yl)butan-1-ol
xref: CHEMBL936
synonym: SK-478
synonym: SK&F-478A
synonym: K-478-A
synonym: SK&F-478-J
synonym: Vontrol®
synonym: Satanolon
approved: t
ligand name: diphenidol
type: SyntheticOrganicLigand

diflunisal
canonical SMILES: Fc1ccc(c(c1)F)c1ccc(c(c1)C(=O)O)O
isomeric SMILES: Fc1ccc(c(c1)F)c1ccc(c(c1)C(=O)O)O
in ch i key: HUPFGZXOMWLGNK-UHFFFAOYSA-N
in ch i: InChI=1S/C13H8F2O3/c14-8-2-3-9(11(15)6-8)7-1-4-12(16)10(5-7)13(17)18/h1-6,16H,(H,17,18)
comment: Diflunisal is a nonsteroidal anti-inflammatory drug (NSAID)
iupac name: 5-(2,4-difluorophenyl)-2-hydroxybenzoic acid
xref: CHEMBL898
synonym: Diflunisal
synonym: Dolobid®
approved: t
ligand name: diflunisal
type: SyntheticOrganicLigand

diethylpropion
canonical SMILES: CCN(C(C(=O)c1ccccc1)C)CC
isomeric SMILES: CCN(C(C(=O)c1ccccc1)C)CC
in ch i key: XXEPPPIWZFICOJ-UHFFFAOYSA-N
in ch i: InChI=1S/C13H19NO/c1-4-14(5-2)11(3)13(15)12-9-7-6-8-10-12/h6-11H,4-5H2,1-3H3
comment: Diethylpropion is a stimulant drug (of the phenethylamine, amphetamine, and cathinone classes) used for its appetite suppressing action.
iupac name: 2-(diethylamino)-1-phenylpropan-1-one
xref: CHEMBL1194666
synonym: Tenuate
synonym: Tepanil
synonym: Tenuate Dospan
synonym: Tepanil Ten-Tab
synonym: diethylpropion hydrochloride
synonym: Prefamone
synonym: Regenon®
approved: t
ligand name: diethylpropion
type: SyntheticOrganicLigand

dienestrol
canonical SMILES: CC=C(C(=CC)c1ccc(cc1)O)c1ccc(cc1)O
isomeric SMILES: C/C=C(/C(=C/C)/c1ccc(cc1)O)/c1ccc(cc1)O
in ch i key: NFDFQCUYFHCNBW-SCGPFSFSSA-N
in ch i: InChI=1S/C18H18O2/c1-3-17(13-5-9-15(19)10-6-13)18(4-2)14-7-11-16(20)12-8-14/h3-12,19-20H,1-2H3/b17-3+,18-4+
comment: Dienestrol is a synthetic, non-steroidal estrogen of the stilbestrol group. It is a close analogue of <Ligand id=2801/>.
iupac name: 4-[(2E,4E)-4-(4-hydroxyphenyl)hexa-2,4-dien-3-yl]phenol
xref: CHEMBL1018
synonym: DV
synonym: Dienestrol
synonym: Estraguard®
approved: t
ligand name: dienestrol
type: SyntheticOrganicLigand

dibucaine
canonical SMILES: CCCCOc1nc2ccccc2c(c1)C(=NCCN(CC)CC)O
isomeric SMILES: CCCCOc1nc2ccccc2c(c1)C(=NCCN(CC)CC)O
in ch i key: PUFQVTATUTYEAL-UHFFFAOYSA-N
in ch i: InChI=1S/C20H29N3O2/c1-4-7-14-25-19-15-17(16-10-8-9-11-18(16)22-19)20(24)21-12-13-23(5-2)6-3/h8-11,15H,4-7,12-14H2,1-3H3,(H,21,24)
comment: Marketed formulations may contain dibucaine hydrochloride (PubChem CID 521951).
iupac name: 2-butoxy-N-[2-(diethylamino)ethyl]quinoline-4-carboximidic acid
xref: CHEMBL1086
synonym: Nupercaine ®
synonym: cincaine chloride
synonym: Heavy Solution Nupercaine
synonym: Nupercainal
synonym: Sovcaine
synonym: Cincain ®
approved: t
ligand name: dibucaine
type: SyntheticOrganicLigand

desvenlafaxine
canonical SMILES: CN(CC(C1(O)CCCCC1)c1ccc(cc1)O)C
isomeric SMILES: CN(CC(C1(O)CCCCC1)c1ccc(cc1)O)C
in ch i key: KYYIDSXMWOZKMP-UHFFFAOYSA-N
in ch i: InChI=1S/C16H25NO2/c1-17(2)12-15(13-6-8-14(18)9-7-13)16(19)10-4-3-5-11-16/h6-9,15,18-19H,3-5,10-12H2,1-2H3
comment: Desvenlafaxine belongs to the group of serotonin–norepinephrine reuptake inhibitors (SNRIs) which are antidepressants. Desvenlafaxine is the major active metabolite of <Ligand id=7321/>.
iupac name: 4-[2-(dimethylamino)-1-(1-hydroxycyclohexyl)ethyl]phenol
xref: CHEMBL1118
synonym: Pristiq®
synonym: WY-45233
synonym: O-desmethylvenlafaxine (ODV)
approved: t
ligand name: desvenlafaxine
type: SyntheticOrganicLigand

desflurane
canonical SMILES: FC(OC(C(F)(F)F)F)F
isomeric SMILES: FC(OC(C(F)(F)F)F)F
in ch i key: DPYMFVXJLLWWEU-UHFFFAOYSA-N
in ch i: InChI=1S/C3H2F6O/c4-1(3(7,8)9)10-2(5)6/h1-2H
comment: Desflurane is a highly fluorinated methyl ethyl ether general anaesthetic. it is a racemic mixture of (R) and (S) optical isomers (enantiomers). We show the chemical structure without specified stereochemistry to represent the mixture. Desflurane is a greenhouse gas.
iupac name: 2-(difluoromethoxy)-1,1,1,2-tetrafluoroethane
xref: CHEMBL1200733
synonym: I-653
synonym: Suprane®
approved: t
ligand name: desflurane
type: SyntheticOrganicLigand

dapiprazole
canonical SMILES: Cc1ccccc1N1CCN(CC1)CCc1nnc2n1CCCC2
isomeric SMILES: Cc1ccccc1N1CCN(CC1)CCc1nnc2n1CCCC2
in ch i key: RFWZESUMWJKKRN-UHFFFAOYSA-N
in ch i: InChI=1S/C19H27N5/c1-16-6-2-3-7-17(16)23-14-12-22(13-15-23)11-9-19-21-20-18-8-4-5-10-24(18)19/h2-3,6-7H,4-5,8-15H2,1H3
comment: Marketed formulations may contain apiprazole hydrochloride (PubChem CID 6917787).
iupac name: 1-(2-methylphenyl)-4-(2-{5H,6H,7H,8H-[1,2,4]triazolo[4,3-a]pyridin-3-yl}ethyl)piperazine
xref: CHEMBL1201216
synonym: AF-2139
synonym: Rev-Eyes®
approved: t
ligand name: dapiprazole
type: SyntheticOrganicLigand

cyclophosphamide
canonical SMILES: ClCCN(P1(=O)NCCCO1)CCCl
isomeric SMILES: ClCCN(P1(=O)NCCCO1)CCCl
in ch i key: CMSMOCZEIVJLDB-UHFFFAOYSA-N
comment: Cyclophosphamide is an alkylating agent of the nitrogen mustard type. It is converted in vivo to the active metabolite 4-hydroxy cyclophosphamide by liver cytochrome P450 (CYP) enzymes. It is used mainly as a cancer chemotherapeutic. It can be used to treat autoimmune conditions, but as it has severe and life-threatening side-effects, other less toxic medications may be the preferred option following an acuteautoimmune crisis. Cyclophosphamide is on the World Health Organisation's List of Essential Medicines. Click here to access the pdf version of the WHO's 21st Essential Medicines list (2019).
iupac name: N,N-bis(2-chloroethyl)-2-oxo-1,3,2$l^{5}-oxazaphosphinan-2-amine
xref: CHEMBL88
synonym: Neosar
synonym: Sendoxan
synonym: Cytoxan®
synonym: Endoxan®
synonym: Procytox
synonym: Revimmune
synonym: cytophosphane
approved: t
ligand name: cyclophosphamide
type: SyntheticOrganicLigand

cyclopentolate
canonical SMILES: CN(CCOC(=O)C(C1(O)CCCC1)c1ccccc1)C
isomeric SMILES: CN(CCOC(=O)C(C1(O)CCCC1)c1ccccc1)C
in ch i key: SKYSRIRYMSLOIN-UHFFFAOYSA-N
in ch i: InChI=1S/C17H25NO3/c1-18(2)12-13-21-16(19)15(14-8-4-3-5-9-14)17(20)10-6-7-11-17/h3-5,8-9,15,20H,6-7,10-13H2,1-2H3
comment: Cyclopentolate is an anti-muscarinic drug similar to <Ligand id=320/> and <Ligand id=330/>.
iupac name: 2-(dimethylamino)ethyl 2-(1-hydroxycyclopentyl)-2-phenylacetate
xref: CHEMBL1201338
synonym: Pentolair
synonym: Akpentolate
synonym: Ak-Pentolate
synonym: Cyclogyl Otic
synonym: Cyclogyl®
synonym: Mydrilate®
approved: t
ligand name: cyclopentolate
type: SyntheticOrganicLigand

cyclobenzaprine
canonical SMILES: CN(CCC=C1c2ccccc2C=Cc2c1cccc2)C
isomeric SMILES: CN(CCC=C1c2ccccc2C=Cc2c1cccc2)C
in ch i key: JURKNVYFZMSNLP-UHFFFAOYSA-N
in ch i: InChI=1S/C20H21N/c1-21(2)15-7-12-20-18-10-5-3-8-16(18)13-14-17-9-4-6-11-19(17)20/h3-6,8-14H,7,15H2,1-2H3
comment: Cyclobenzaprine is a tricyclic antidepressant similar to <Ligand id=200/>. It acts as a skeletal muscle relaxant and central nervous system (CNS) depressant.
iupac name: 3-(dibenzo[1,2-a:1',2'-e][7]annulen-11-ylidene)-N,N-dimethylpropan-1-amine
xref: CHEMBL669
synonym: Flexeril
synonym: MK-130
synonym: Fexmid
synonym: Amrix®
approved: t
ligand name: cyclobenzaprine
type: SyntheticOrganicLigand

cyclizine
canonical SMILES: CN1CCN(CC1)C(c1ccccc1)c1ccccc1
isomeric SMILES: CN1CCN(CC1)C(c1ccccc1)c1ccccc1
in ch i key: UVKZSORBKUEBAZ-UHFFFAOYSA-N
in ch i: InChI=1S/C18H22N2/c1-19-12-14-20(15-13-19)18(16-8-4-2-5-9-16)17-10-6-3-7-11-17/h2-11,18H,12-15H2,1H3
comment: Cyclizine is an antihistamine drug used primarily for its anti-nausea and antiemetic actions. Cyclizine is on the World Health Organisation's List of Essential Medicines. Click here to access the pdf version of the WHO's 21st Essential Medicines list (2019).
iupac name: 1-(diphenylmethyl)-4-methylpiperazine
xref: CHEMBL648
synonym: Marezine®
approved: t
ligand name: cyclizine
type: SyntheticOrganicLigand

clopidogrel
canonical SMILES: COC(=O)C(c1ccccc1Cl)N1CCc2c(C1)ccs2
isomeric SMILES: COC(=O)[C@H](c1ccccc1Cl)N1CCc2c(C1)ccs2
in ch i key: GKTWGGQPFAXNFI-HNNXBMFYSA-N
in ch i: InChI=1S/C16H16ClNO2S/c1-20-16(19)15(12-4-2-3-5-13(12)17)18-8-6-14-11(10-18)7-9-21-14/h2-5,7,9,15H,6,8,10H2,1H3/t15-/m0/s1
comment: Clopidogrel is a prodrug converted by liver CYP450 via 2-oxo-clopidogrel to an active metabolite, listed in GtoPdb as <Ligand id=1772/> <Reference id=5917/>. Marketed formulations may contain clopidogrel bisulfate (PubChem CID 115366).
iupac name: methyl (2S)-2-(2-chlorophenyl)-2-{4H,5H,6H,7H-thieno[3,2-c]pyridin-5-yl}acetate
xref: CHEMBL1771
synonym: Iscover®
synonym: Plavix&reg
synonym: SR-25990C
approved: t
ligand name: clopidogrel
type: SyntheticOrganicLigand

cilostazol
in ch i key: RRGUKTPIGVIEKM-UHFFFAOYSA-N
in ch i: InChI=1S/C20H27N5O2/c26-20-12-9-15-14-17(10-11-18(15)21-20)27-13-5-4-8-19-22-23-24-25(19)16-6-2-1-3-7-16/h10-11,14,16H,1-9,12-13H2,(H,21,26)
comment: Cilostazol is a quinolinone-derivative phosphodiesterase (PDE) inhibitor.
iupac name: 6-[4-(1-cyclohexyl-1H-1,2,3,4-tetrazol-5-yl)butoxy]-1,2,3,4-tetrahydroquinolin-2-one
xref: CHEMBL799
synonym: OPC-13013
synonym: OPC-21
synonym: Pletal®
approved: t
ligand name: cilostazol
type: SyntheticOrganicLigand

chlorthalidone
in ch i key: JIVPVXMEBJLZRO-UHFFFAOYSA-N
comment: Chlorthalidone is a thiazide-like diuretic. It has a longer duration of action than other thiazide drugs.
iupac name: 2-chloro-5-(1,3-dihydroxy-1H-isoindol-1-yl)benzene-1-sulfonamide
xref: CHEMBL1055
synonym: G-33182
synonym: Thalitone
synonym: Chlorthalidone
synonym: Hygroton®
approved: t
ligand name: chlorthalidone
type: SyntheticOrganicLigand

chlorotrianisene
in ch i key: BFPSDSIWYFKGBC-UHFFFAOYSA-N
in ch i: InChI=1S/C23H21ClO3/c1-25-19-10-4-16(5-11-19)22(17-6-12-20(26-2)13-7-17)23(24)18-8-14-21(27-3)15-9-18/h4-15H,1-3H3
comment: Chlorotrianisene is a non-steroidal estrogen mimic.
iupac name: 1-[2-chloro-1,2-bis(4-methoxyphenyl)ethenyl]-4-methoxybenzene
xref: CHEMBL1200761
synonym: Tace®
synonym: chlortrianisestrol
approved: t
ligand name: chlorotrianisene
type: SyntheticOrganicLigand

chloroprocaine
canonical SMILES: CCN(CCOC(=O)c1ccc(cc1Cl)N)CC
isomeric SMILES: CCN(CCOC(=O)c1ccc(cc1Cl)N)CC
in ch i key: VDANGULDQQJODZ-UHFFFAOYSA-N
in ch i: InChI=1S/C13H19ClN2O2/c1-3-16(4-2)7-8-18-13(17)11-6-5-10(15)9-12(11)14/h5-6,9H,3-4,7-8,15H2,1-2H3
comment: Chloroprocaine is a short-acting ester anaesthetic. It has a significantly shorter duration of action than <Ligand id=2623/> and is significantly less toxic.
iupac name: 2-(diethylamino)ethyl 4-amino-2-chlorobenzoate
xref: CHEMBL1179047
synonym: Nesacaine-Mpf
synonym: Nesacaine®
synonym: chloroprocaine hydrochloride
approved: t
ligand name: chloroprocaine
type: SyntheticOrganicLigand

chlorambucil
canonical SMILES: ClCCN(c1ccc(cc1)CCCC(=O)O)CCCl
isomeric SMILES: ClCCN(c1ccc(cc1)CCCC(=O)O)CCCl
in ch i key: JCKYGMPEJWAADB-UHFFFAOYSA-N
in ch i: InChI=1S/C14H19Cl2NO2/c15-8-10-17(11-9-16)13-6-4-12(5-7-13)2-1-3-14(18)19/h4-7H,1-3,8-11H2,(H,18,19)
comment: Chlorambucil is a DNA alkylating agent.
iupac name: 4-{4-[bis(2-chloroethyl)amino]phenyl}butanoic acid
xref: CHEMBL515
synonym: chlorbutin
synonym: Leukeran®
approved: t
ligand name: chlorambucil
type: SyntheticOrganicLigand

carteolol
canonical SMILES: OC(COc1cccc2c1CCC(=N2)O)CNC(C)(C)C
isomeric SMILES: OC(COc1cccc2c1CCC(=N2)O)CNC(C)(C)C
in ch i key: LWAFSWPYPHEXKX-UHFFFAOYSA-N
in ch i: InChI=1S/C16H24N2O3/c1-16(2,3)17-9-11(19)10-21-14-6-4-5-13-12(14)7-8-15(20)18-13/h4-6,11,17,19H,7-10H2,1-3H3,(H,18,20)
comment: Carteolol is a β-blocker, selective for β1-adrenoceptors in cardiac tissue.
iupac name: 5-[3-(tert-butylamino)-2-hydroxypropoxy]-3,4-dihydroquinolin-2-ol
xref: CHEMBL839
synonym: Carteolol
synonym: Carteolol Hydrochloride
synonym: Cartrol®
synonym: Ocupress®
synonym: OPC-1085
synonym: ABBOTT-43326
approved: t
ligand name: carteolol
type: SyntheticOrganicLigand

carprofen
canonical SMILES: OC(=O)C(c1ccc2c(c1)[nH]c1c2cc(cc1)Cl)C
isomeric SMILES: OC(=O)C(c1ccc2c(c1)[nH]c1c2cc(cc1)Cl)C
in ch i key: PUXBGTOOZJQSKH-UHFFFAOYSA-N
in ch i: InChI=1S/C15H12ClNO2/c1-8(15(18)19)9-2-4-11-12-7-10(16)3-5-13(12)17-14(11)6-9/h2-8,17H,1H3,(H,18,19)
comment: Carprofen is a non-steroidal anti-inflammatory drug (NSAID), although it is no longer marketed for human use and now seems to be used exclusively by vets.
iupac name: 2-(6-chloro-9H-carbazol-2-yl)propanoic acid
xref: CHEMBL1316
synonym: Rimadyl
synonym: Ro-205720000
approved: t
ligand name: carprofen
type: SyntheticOrganicLigand

carphenazine
in ch i key: XZSMZRXAEFNJCU-UHFFFAOYSA-N
in ch i: InChI=1S/C24H31N3O2S/c1-2-22(29)19-8-9-24-21(18-19)27(20-6-3-4-7-23(20)30-24)11-5-10-25-12-14-26(15-13-25)16-17-28/h3-4,6-9,18,28H,2,5,10-17H2,1H3
comment: Carphenazine is an antipsychotic drug. There is no information regarding approval for clinical use of this drug on the US FDA website. Other national approval agencies may have granted marketing authorisation. The Electronic Medicines Compendium (eMC) lists buclizine only as an active ingredient in a multi-component, anti-migraine treatment alongside paracetamol and codeine. Marketed formulations may contain carphenazine maleate (PubChem CID 20838085).
iupac name: 1-(10-{3-[4-(2-hydroxyethyl)piperazin-1-yl]propyl}-10H-phenothiazin-2-yl)propan-1-one
xref: CHEMBL1201328
synonym: Proketazine®
synonym: WY-2445
approved: t
ligand name: carphenazine
type: SyntheticOrganicLigand

carbinoxamine
canonical SMILES: CN(CCOC(c1ccccn1)c1ccc(cc1)Cl)C
isomeric SMILES: CN(CCOC(c1ccccn1)c1ccc(cc1)Cl)C
in ch i key: OJFSXZCBGQGRNV-UHFFFAOYSA-N
in ch i: InChI=1S/C16H19ClN2O/c1-19(2)11-12-20-16(15-5-3-4-10-18-15)13-6-8-14(17)9-7-13/h3-10,16H,11-12H2,1-2H3
comment: Carbinoxamine is an antihistamine.
iupac name: {2-[(4-chlorophenyl)(pyridin-2-yl)methoxy]ethyl}dimethylamine
xref: CHEMBL864
synonym: carbinoxamine maleate
synonym: Clistin®
approved: t
ligand name: carbinoxamine
type: SyntheticOrganicLigand

butalbital
canonical SMILES: C=CCC1(CC(C)C)C(=NC(=O)N=C1O)O
isomeric SMILES: C=CCC1(CC(C)C)C(=NC(=O)N=C1O)O
in ch i key: UZVHFVZFNXBMQJ-UHFFFAOYSA-N
in ch i: InChI=1S/C11H16N2O3/c1-4-5-11(6-7(2)3)8(14)12-10(16)13-9(11)15/h4,7H,1,5-6H2,2-3H3,(H2,12,13,14,15,16)
comment: Butalbital is a barbiturate drug.
iupac name: 4,6-dihydroxy-5-(2-methylpropyl)-5-(prop-2-en-1-yl)-2,5-dihydropyrimidin-2-one
xref: CHEMBL454
synonym: tetrallobarbital
synonym: alisobumal
synonym: allylbarbituric acid
synonym: itobarbital
approved: t
ligand name: butalbital
type: SyntheticOrganicLigand

butabarbital
canonical SMILES: CCC(C1(CC)C(=NC(=O)N=C1O)O)C
isomeric SMILES: CCC(C1(CC)C(=NC(=O)N=C1O)O)C
in ch i key: ZRIHAIZYIMGOAB-UHFFFAOYSA-N
in ch i: InChI=1S/C10H16N2O3/c1-4-6(3)10(5-2)7(13)11-9(15)12-8(10)14/h6H,4-5H2,1-3H3,(H2,11,12,13,14,15)
comment: Butabarbital is a prescription barbiturate sedative. It is used in relatively few countries due to its potential for abuse and dangerous interaction in combination with alcohol.
iupac name: 5-(butan-2-yl)-5-ethyl-4,6-dihydroxy-2,5-dihydropyrimidin-2-one
xref: CHEMBL449
synonym: Butalan
synonym: Sarisol
synonym: Butabarb
synonym: Buticaps
synonym: Butabarbital
synonym: Sarisol No. 1
synonym: Sarisol No. 2
synonym: Butisol Sodium
synonym: Butabarbital Sodium
synonym: Sodium Butabarbital
synonym: Butisol®
approved: t
ligand name: butabarbital
type: SyntheticOrganicLigand

busulfan
canonical SMILES: CS(=O)(=O)OCCCCOS(=O)(=O)C
isomeric SMILES: CS(=O)(=O)OCCCCOS(=O)(=O)C
in ch i key: COVZYZSDYWQREU-UHFFFAOYSA-N
in ch i: InChI=1S/C6H14O6S2/c1-13(7,8)11-5-3-4-6-12-14(2,9)10/h3-6H2,1-2H3
comment: Busulfan is a DNA alkylating agent. It has an immunosuppressive effect on bone marrow, especially inhibiting growth of granulocytes.
iupac name: 4-(methanesulfonyloxy)butyl methanesulfonate
xref: CHEMBL820
synonym: Busulfex IV®
synonym: Myleran®
approved: t
ligand name: busulfan
type: SyntheticOrganicLigand

bupropion
canonical SMILES: Clc1cccc(c1)C(=O)C(NC(C)(C)C)C
isomeric SMILES: Clc1cccc(c1)C(=O)C(NC(C)(C)C)C
in ch i key: SNPPWIUOZRMYNY-UHFFFAOYSA-N
in ch i: InChI=1S/C13H18ClNO/c1-9(15-13(2,3)4)12(16)10-6-5-7-11(14)8-10/h5-9,15H,1-4H3
comment: The approval status for use of this drug was submitted for re-evaluation by the European Medicines Agency in 2002, following public health concerns around serious adverse reactions associated with its use. These included depression, suicidal thoughts, suicide, seizures, undesirable cardiovascular effects, and angioedema. EU Member States regulatory authorities agreed to keep the product under regular review. Marketed formulations usually contain bupropion hydrochloride (PubChem CID 62884).
iupac name: 2-(tert-butylamino)-1-(3-chlorophenyl)propan-1-one
xref: CHEMBL894
synonym: amfebutamone
synonym: BW-323
synonym: Aplenzin
synonym: Forfivo Xl
synonym: Wellbutrin Sr
synonym: Wellbutrin Xl
synonym: Bupropion Hydrochloride
synonym: Wellbutrin®
synonym: Zyban®
approved: t
ligand name: bupropion
type: SyntheticOrganicLigand

buclizine
in ch i key: MOYGZHXDRJNJEP-UHFFFAOYSA-N
in ch i: InChI=1S/C28H33ClN2/c1-28(2,3)25-13-9-22(10-14-25)21-30-17-19-31(20-18-30)27(23-7-5-4-6-8-23)24-11-15-26(29)16-12-24/h4-16,27H,17-21H2,1-3H3
comment: Buclizine is a piperazine derivative antihistamine and anticholinergic drug, with antiemetic properties.
iupac name: 1-[(4-tert-butylphenyl)methyl]-4-[(4-chlorophenyl)(phenyl)methyl]piperazine
xref: CHEMBL1201271
synonym: Bucladin-S
synonym: UCB-4445
approved: t
ligand name: buclizine
type: SyntheticOrganicLigand

bisoprolol
canonical SMILES: OC(COc1ccc(cc1)COCCOC(C)C)CNC(C)C
isomeric SMILES: OC(COc1ccc(cc1)COCCOC(C)C)CNC(C)C
in ch i key: VHYCDWMUTMEGQY-UHFFFAOYSA-N
in ch i: InChI=1S/C18H31NO4/c1-14(2)19-11-17(20)13-23-18-7-5-16(6-8-18)12-21-9-10-22-15(3)4/h5-8,14-15,17,19-20H,9-13H2,1-4H3
comment: Bisoprolol is a β-blocker, selective for β1-adrenoceptors in cardiac tissue. The S(-) enantiomer is believed to account for most of its β-blocking activity. Marketed formulations may contain bisoprolol fumarate (PubChem CID 6917733).
xref: CHEMBL645
synonym: EMD-33512
synonym: CL-297939
synonym: Zebeta®
approved: t
ligand name: bisoprolol
type: SyntheticOrganicLigand

biperiden
canonical SMILES: OC(C1CC2CC1C=C2)(c1ccccc1)CCN1CCCCC1
isomeric SMILES: OC(C1CC2CC1C=C2)(c1ccccc1)CCN1CCCCC1
in ch i key: YSXKPIUOCJLQIE-UHFFFAOYSA-N
in ch i: InChI=1S/C21H29NO/c23-21(19-7-3-1-4-8-19,11-14-22-12-5-2-6-13-22)20-16-17-9-10-18(20)15-17/h1,3-4,7-10,17-18,20,23H,2,5-6,11-16H2
comment: Biperiden is a centrally active anticholinergic drug.
iupac name: 1-{bicyclo[2.2.1]hept-5-en-2-yl}-1-phenyl-3-(piperidin-1-yl)propan-1-ol
xref: CHEMBL1101
synonym: Akineton®
synonym: biperiden HCl
synonym: biperiden lactate
approved: t
ligand name: biperiden
type: SyntheticOrganicLigand

betazole
canonical SMILES: NCCc1cc[nH]n1
isomeric SMILES: NCCc1cc[nH]n1
in ch i key: JXDFEQONERDKSS-UHFFFAOYSA-N
in ch i: InChI=1S/C5H9N3/c6-3-1-5-2-4-7-8-5/h2,4H,1,3,6H2,(H,7,8)
comment: Betazole is a derivative of <Ligand id=7061/>.
iupac name: 2-(1H-pyrazol-3-yl)ethan-1-amine
xref: CHEMBL1201323
synonym: ametazole
synonym: Histalog®
approved: t
ligand name: betazole
type: SyntheticOrganicLigand

benzthiazide
in ch i key: NDTSRXAMMQDVSW-UHFFFAOYSA-N
comment: Benzthiazide is a thiazide diuretic. It is no longer available in the US or UK, but marketing may be authorised by other national approval agencies.
iupac name: 3-(benzylsulfanylmethyl)-6-chloro-1,1-dioxo-4H-1$l^{6},2,4-benzothiadiazine-7-sulfonamide
xref: CHEMBL1201039
synonym: EXNA
synonym: Urese
synonym: Aquatag®
synonym: Fovane®
approved: t
ligand name: benzthiazide
type: SyntheticOrganicLigand

benzquinamide
in ch i key: JSZILQVIPPROJI-UHFFFAOYSA-N
in ch i: InChI=1S/C22H32N2O5/c1-6-23(7-2)22(26)17-13-24-9-8-15-10-20(27-4)21(28-5)11-16(15)18(24)12-19(17)29-14(3)25/h10-11,17-19H,6-9,12-13H2,1-5H3
comment: Benzquinamide is a largely discontinued antiemetic drug.
iupac name: 3-(diethylcarbamoyl)-9,10-dimethoxy-1H,2H,3H,4H,6H,7H,11bH-pyrido[2,1-a]isoquinolin-2-yl acetate
xref: CHEMBL1201250
synonym: Emete-Con
synonym: P-2647
synonym: Quantril®
approved: t
ligand name: benzquinamide
type: SyntheticOrganicLigand

oxybuprocaine
canonical SMILES: CCCCOc1cc(ccc1N)C(=O)OCCN(CC)CC
isomeric SMILES: CCCCOc1cc(ccc1N)C(=O)OCCN(CC)CC
in ch i key: CMHHMUWAYWTMGS-UHFFFAOYSA-N
in ch i: InChI=1S/C17H28N2O3/c1-4-7-11-21-16-13-14(8-9-15(16)18)17(20)22-12-10-19(5-2)6-3/h8-9,13H,4-7,10-12,18H2,1-3H3
comment: Oxybuprocaine is an ester-type local anaesthetic, useful in ophthalmology and otolaryngology procedures.
iupac name: 2-(diethylamino)ethyl 4-amino-3-butoxybenzoate
xref: CHEMBL1200
synonym: benoxinate hydrochloride
synonym: Novesine
synonym: Novesin
synonym: Minims Oxybuprocaine®
approved: t
ligand name: oxybuprocaine
type: SyntheticOrganicLigand

bendroflumethiazide
in ch i key: HDWIHXWEUNVBIY-UHFFFAOYSA-N
comment: Bendroflumethiazide is a thiazide diuretic.
iupac name: 3-benzyl-1,1-dioxo-6-(trifluoromethyl)-3,4-dihydro-2H-1$l^{6},2,4-benzothiadiazine-7-sulfonamide
xref: CHEMBL1684
synonym: Naturetin-5
synonym: Naturetin-10
synonym: Naturetin-2.5
synonym: Naturetin®
synonym: Aprinox®
approved: t
ligand name: bendroflumethiazide
type: SyntheticOrganicLigand

azelastine
in ch i key: MBUVEWMHONZEQD-UHFFFAOYSA-N
in ch i: InChI=1S/C22H24ClN3O/c1-25-13-4-5-18(12-14-25)26-22(27)20-7-3-2-6-19(20)21(24-26)15-16-8-10-17(23)11-9-16/h2-3,6-11,18H,4-5,12-15H2,1H3
comment: There is no information regarding approval for clinical use of this drug on the US FDA website. Other national approval agencies may have granted marketing authorisation.
iupac name: 4-[(4-chlorophenyl)methyl]-2-(1-methylazepan-4-yl)-1,2-dihydrophthalazin-1-one
xref: CHEMBL639
synonym: A-5610
synonym: E-0659
synonym: W-2979M
synonym: Astepro
synonym: Optivar
synonym: Optilast
synonym: Azelastine Hydrochloride
synonym: Rhinolast®
synonym: Astelin®
approved: t
ligand name: azelastine
type: SyntheticOrganicLigand

azathioprine
canonical SMILES: Cn1cnc(c1Sc1ncnc2c1nc[nH]2)N(=O)=O
isomeric SMILES: Cn1cnc(c1Sc1ncnc2c1nc[nH]2)N(=O)=O
in ch i key: LMEKQMALGUDUQG-UHFFFAOYSA-N
in ch i: InChI=1S/C9H7N7O2S/c1-15-4-14-7(16(17)18)9(15)19-8-5-6(11-2-10-5)12-3-13-8/h2-4H,1H3,(H,10,11,12,13)
comment: Azathioprine is an immunosuppressive antimetabolite. The active drug is believed to be <Ligand id=7226/>. Marketed formulations may contain azathioprine sodium (PubChem CID 23678403).
iupac name: 6-[(1-methyl-4-nitro-1H-imidazol-5-yl)sulfanyl]-9H-purine
xref: CHEMBL1542
synonym: Azathioprine
synonym: BW-57-322
synonym: Azasan®
synonym: Imuran®
synonym: Jayempi®
approved: t
ligand name: azathioprine
type: SyntheticOrganicLigand

azatadine
canonical SMILES: CN1CCC(=C2c3ccccc3CCc3c2nccc3)CC1
isomeric SMILES: CN1CCC(=C2c3ccccc3CCc3c2nccc3)CC1
in ch i key: SEBMTIQKRHYNIT-UHFFFAOYSA-N
in ch i: InChI=1S/C20H22N2/c1-22-13-10-16(11-14-22)19-18-7-3-2-5-15(18)8-9-17-6-4-12-21-20(17)19/h2-7,12H,8-11,13-14H2,1H3
comment: Azatadine is a first-generation antihistamine and anticholinergic drug. Its marketing has been discontinued in many countries as its use has largely been repleaced by newer and more effective alternatives.
iupac name: 11-(1-methylpiperidin-4-ylidene)-5,6-dihydrobenzo[1,2]cyclohepta[3,4-b]pyridine
xref: CHEMBL946
synonym: Optimine®
synonym: SCH-10649
synonym: Idumed
synonym: Zadine
approved: t
ligand name: azatadine
type: SyntheticOrganicLigand

atomoxetine
canonical SMILES: CNCCC(c1ccccc1)Oc1ccccc1C
isomeric SMILES: CNCC[C@H](c1ccccc1)Oc1ccccc1C
in ch i key: VHGCDTVCOLNTBX-QGZVFWFLSA-N
in ch i: InChI=1S/C17H21NO/c1-14-8-6-7-11-16(14)19-17(12-13-18-2)15-9-4-3-5-10-15/h3-11,17-18H,12-13H2,1-2H3/t17-/m1/s1
comment: Atomoxetine is primarily a norepinephrine (noradrenaline) reuptake inhibitor (NRI), with weak inhibitory effects on SERT (serotonin reuptake), and DAT (dopamine reuptake).
iupac name: methyl[(3R)-3-(2-methylphenoxy)-3-phenylpropyl]amine
xref: CHEMBL641
synonym: LY-139603
synonym: Atomoxetine Hydrochloride
synonym: Strattera®
approved: t
ligand name: atomoxetine
type: SyntheticOrganicLigand

apraclonidine
canonical SMILES: Nc1cc(Cl)c(c(c1)Cl)NC1=NCCN1
isomeric SMILES: Nc1cc(Cl)c(c(c1)Cl)NC1=NCCN1
in ch i key: IEJXVRYNEISIKR-UHFFFAOYSA-N
in ch i: InChI=1S/C9H10Cl2N4/c10-6-3-5(12)4-7(11)8(6)15-9-13-1-2-14-9/h3-4H,1-2,12H2,(H2,13,14,15)
comment: Apraclonidine is a <Ligand id=516/> derivative which acts as sympathomimetic α2-adrenoceptor agonist.
iupac name: 2,6-dichloro-1-N-(4,5-dihydro-1H-imidazol-2-yl)benzene-1,4-diamine
xref: CHEMBL647
synonym: AL-02145
synonym: Apraclonidine Hydrochloride
synonym: Iopidine®
approved: t
ligand name: apraclonidine
type: SyntheticOrganicLigand

antazoline
canonical SMILES: c1ccc(cc1)CN(c1ccccc1)CC1=NCCN1
isomeric SMILES: c1ccc(cc1)CN(c1ccccc1)CC1=NCCN1
in ch i key: REYFJDPCWQRWAA-UHFFFAOYSA-N
in ch i: InChI=1S/C17H19N3/c1-3-7-15(8-4-1)13-20(14-17-18-11-12-19-17)16-9-5-2-6-10-16/h1-10H,11-14H2,(H,18,19)
comment: There is no information regarding approval for clinical use of this drug on the US FDA website. Other national approval agencies may have granted marketing authorisation.
iupac name: N-benzyl-N-(4,5-dihydro-1H-imidazol-2-ylmethyl)aniline
xref: CHEMBL1305
synonym: vasocon-A
synonym: Otrivine antistin
approved: t
ligand name: antazoline
type: SyntheticOrganicLigand

anileridine
in ch i key: LKYQLAWMNBFNJT-UHFFFAOYSA-N
in ch i: InChI=1S/C22H28N2O2/c1-2-26-21(25)22(19-6-4-3-5-7-19)13-16-24(17-14-22)15-12-18-8-10-20(23)11-9-18/h3-11H,2,12-17,23H2,1H3
comment: A piperidine analgesic, similar to pethidine but with improved analgesic activity. Marketed formulations may contain anileridine hydrochloride (PubChem CID 197194) or anileridine phosphate (PubChem CID 16051989).
iupac name: ethyl 1-[2-(4-aminophenyl)ethyl]-4-phenylpiperidine-4-carboxylate
xref: CHEMBL1201347
synonym: Leritine®
approved: t
ligand name: anileridine
type: SyntheticOrganicLigand

anagrelide
canonical SMILES: OC1=NC2=Nc3c(CN2C1)c(Cl)c(cc3)Cl
isomeric SMILES: OC1=NC2=Nc3c(CN2C1)c(Cl)c(cc3)Cl
in ch i key: OTBXOEAOVRKTNQ-UHFFFAOYSA-N
in ch i: InChI=1S/C10H7Cl2N3O/c11-6-1-2-7-5(9(6)12)3-15-4-8(16)14-10(15)13-7/h1-2H,3-4H2,(H,13,14,16)
comment: Anagrelide is a phosphodiesterase inhibitor with antiplatelet activity <Reference id=24054/>.
iupac name: 6,7-dichloro-3H,5H-imidazo[2,1-b]quinazolin-2-ol
xref: CHEMBL760
synonym: Xagrid®
synonym: Anagrelide Hydrochloride
synonym: Agrylin®
synonym: BL-4162a
approved: t
ligand name: anagrelide
type: SyntheticOrganicLigand

amlexanox
in ch i key: SGRYPYWGNKJSDL-UHFFFAOYSA-N
in ch i: InChI=1S/C16H14N2O4/c1-7(2)8-3-4-12-9(5-8)13(19)10-6-11(16(20)21)14(17)18-15(10)22-12/h3-7H,1-2H3,(H2,17,18)(H,20,21)
comment: Amlexanox has anti-inflammatory <Reference id=24021/>, antiallergic and immunomodulatory actions <Reference id=24024/>. Proposed to inhibit IKKδ and TBK1, albeit with low potency <Reference id=33166/>.
iupac name: 2-amino-5-oxo-7-(propan-2-yl)-5H-chromeno[2,3-b]pyridine-3-carboxylic acid
xref: CHEMBL1096
synonym: AA-673
synonym: CHX-3673
synonym: Aphthasol®
synonym: Amlexanox®
approved: t
ligand name: amlexanox
type: SyntheticOrganicLigand

altretamine
canonical SMILES: CN(c1nc(nc(n1)N(C)C)N(C)C)C
isomeric SMILES: CN(c1nc(nc(n1)N(C)C)N(C)C)C
in ch i key: UUVWYPNAQBNQJQ-UHFFFAOYSA-N
in ch i: InChI=1S/C9H18N6/c1-13(2)7-10-8(14(3)4)12-9(11-7)15(5)6/h1-6H3
comment: Altretamine is a DNA alkylating agent
iupac name: 2-N,2-N,4-N,4-N,6-N,6-N-hexamethyl-1,3,5-triazine-2,4,6-triamine
xref: CHEMBL1455
synonym: Hexalen®
approved: t
ligand name: altretamine
type: SyntheticOrganicLigand

almotriptan
in ch i key: WKEMJKQOLOHJLZ-UHFFFAOYSA-N
in ch i: InChI=1S/C17H25N3O2S/c1-19(2)10-7-15-12-18-17-6-5-14(11-16(15)17)13-23(21,22)20-8-3-4-9-20/h5-6,11-12,18H,3-4,7-10,13H2,1-2H3
comment: Almotriptan is a triptan (tryptamine-based) drug that acts as an agonist of serotonin 5-HT1B/1D receptors <Reference id=38134/>. It is used to treat migraine headaches but does not prevent or cure them.
iupac name: dimethyl(2-{5-[(pyrrolidine-1-sulfonyl)methyl]-1H-indol-3-yl}ethyl)amine
xref: CHEMBL1505
synonym: Almogran®
synonym: Axert®
synonym: LAS-31416
synonym: PNU-180638E
approved: t
ligand name: almotriptan
type: SyntheticOrganicLigand

alfuzosin
in ch i key: WNMJYKCGWZFFKR-UHFFFAOYSA-N
in ch i: InChI=1S/C19H27N5O4/c1-24(8-5-7-21-18(25)14-6-4-9-28-14)19-22-13-11-16(27-3)15(26-2)10-12(13)17(20)23-19/h10-11,14H,4-9H2,1-3H3,(H,21,25)(H2,20,22,23)
comment: Alfuzosin is an α1-adrenergic receptor antagonist.
iupac name: N-{3-[(4-imino-6,7-dimethoxy-3,4-dihydroquinazolin-2-yl)(methyl)amino]propyl}oxolane-2-carboximidic acid
xref: CHEMBL709
synonym: SL-77499-10
synonym: SL-7749910
synonym: Alfuzosin Hydrochloride
synonym: Uroxatral®
approved: t
ligand name: alfuzosin
type: SyntheticOrganicLigand

alfentanil
in ch i key: IDBPHNDTYPBSNI-UHFFFAOYSA-N
in ch i: InChI=1S/C21H32N6O3/c1-4-19(28)27(18-9-7-6-8-10-18)21(17-30-3)11-13-24(14-12-21)15-16-26-20(29)25(5-2)22-23-26/h6-10H,4-5,11-17H2,1-3H3
comment: Alfentanil is an opioid analgesic.
iupac name: N-{1-[2-(4-ethyl-5-oxo-4,5-dihydro-1H-1,2,3,4-tetrazol-1-yl)ethyl]-4-(methoxymethyl)piperidin-4-yl}-N-phenylpropanamide
xref: CHEMBL634
synonym: Alfentanil
synonym: Alfenta®
synonym: Rapifen®
synonym: R-39209
approved: t
ligand name: alfentanil
type: SyntheticOrganicLigand

acebutolol
in ch i key: GOEMGAFJFRBGGG-UHFFFAOYSA-N
in ch i: InChI=1S/C18H28N2O4/c1-5-6-18(23)20-14-7-8-17(16(9-14)13(4)21)24-11-15(22)10-19-12(2)3/h7-9,12,15,19,22H,5-6,10-11H2,1-4H3,(H,20,23)
comment: Acebutolol is a β-blocker.
iupac name: N-(3-acetyl-4-{2-hydroxy-3-[(propan-2-yl)amino]propoxy}phenyl)butanimidic acid
xref: CHEMBL642
synonym: IL-17803A
synonym: Acebutolol Hydrochloride
synonym: Sectral®
approved: t
ligand name: acebutolol
type: SyntheticOrganicLigand

acamprosate
canonical SMILES: CC(=NCCCS(=O)(=O)O)O
isomeric SMILES: CC(=NCCCS(=O)(=O)O)O
in ch i key: AFCGFAGUEYAMAO-UHFFFAOYSA-N
in ch i: InChI=1S/C5H11NO4S/c1-5(7)6-3-2-4-11(8,9)10/h2-4H2,1H3,(H,6,7)(H,8,9,10)
comment: Acamprosate is a NMDA glutamate receptor antagonist and a positive allosteric modulator of GABAA receptors. Marketed formulations contain acamprosate calcium (PubChem CID 155434).
iupac name: N-(3-sulfopropyl)ethanimidic acid
xref: CHEMBL1201293
synonym: Campral®
approved: t
ligand name: acamprosate
type: SyntheticOrganicLigand

vinorelbine
in ch i key: GBABOYUKABKIAF-IELIFDKJSA-N
in ch i: InChI=1S/C45H54N4O8/c1-8-27-19-28-22-44(40(51)55-6,36-30(25-48(23-27)24-28)29-13-10-11-14-33(29)46-36)32-20-31-34(21-35(32)54-5)47(4)38-43(31)16-18-49-17-12-15-42(9-2,37(43)49)39(57-26(3)50)45(38,53)41(52)56-7/h10-15,19-21,28,37-39,46,53H,8-9,16-18,22-25H2,1-7H3/t28-,37-,38+,39+,42+,43+,44-,45-/m0/s1
comment: Vinorelbine is an anti-mitotic chemotherapy drug.
xref: CHEMBL553025
synonym: Navelbine®
approved: t
ligand name: vinorelbine
type: NaturalProductLigand

travoprost
isomeric SMILES: CC(OC(=O)CCC/C=C/C[C@H]1[C@@H](O)C[C@H]([C@@H]1/C=C/[C@H](COc1cccc(c1)C(F)(F)F)O)O)C
in ch i key: MKPLKVHSHYCHOC-AHTXBMBWSA-N
in ch i: InChI=1S/C26H35F3O6/c1-17(2)35-25(33)11-6-4-3-5-10-21-22(24(32)15-23(21)31)13-12-19(30)16-34-20-9-7-8-18(14-20)26(27,28)29/h3,5,7-9,12-14,17,19,21-24,30-32H,4,6,10-11,15-16H2,1-2H3/b5-3-,13-12+/t19-,21-,22-,23+,24-/m1/s1
comment: Travoprost is an analogue of prostaglindin F2α (<Ligand id=1884/>). The drug itself is a prodrug that is hydrolysed in vivo to an active free acid form.
iupac name: propan-2-yl (5Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3R)-3-hydroxy-4-[3-(trifluoromethyl)phenoxy]but-1-en-1-yl]cyclopentyl]hept-5-enoate
xref: CHEMBL1200799
synonym: AL-6221
synonym: Travatan Z
synonym: Travatan®
approved: t
ligand name: travoprost
type: NaturalProductLigand

topotecan
in ch i key: UCFGDBYHRUNTLO-QHCPKHFHSA-N
in ch i: InChI=1S/C23H23N3O5/c1-4-23(30)16-8-18-20-12(9-26(18)21(28)15(16)11-31-22(23)29)7-13-14(10-25(2)3)19(27)6-5-17(13)24-20/h5-8,27,30H,4,9-11H2,1-3H3/t23-/m0/s1
comment: Topotecan is a semisynthetic analogue of the natural plant alkaloid camptothecin (PubChem CID 24360). Camptothecin was first isolated from the bark and stem of Camptotheca acuminata, the Chinsese happy tree. Topotecan is an anticancer drug which causes DNA strand breaks and leads to cell-cycle arrest and cell death. Marketed formulations may contain topotecan hydrochloride (PubChem CID 60699).
xref: CHEMBL84
synonym: Hycamptin
synonym: Hycamtin®
synonym: SK-S-104864-A
synonym: Potactasol
approved: t
ligand name: topotecan
type: SyntheticOrganicLigand

testosterone propionate
in ch i key: PDMMFKSKQVNJMI-BLQWBTBKSA-N
in ch i: InChI=1S/C22H32O3/c1-4-20(24)25-19-8-7-17-16-6-5-14-13-15(23)9-11-21(14,2)18(16)10-12-22(17,19)3/h13,16-19H,4-12H2,1-3H3/t16-,17-,18-,19-,21-,22-/m0/s1
comment: Testosterone propionate is an anabolic steroid. In vivo testosterone propionate is hydrolysed to testosterone which is the active compound.
iupac name: [(8R,9S,10R,13S,14S,17S)-10,13-dimethyl-3-oxo-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl] propanoate
xref: CHEMBL1170
approved: t
ligand name: testosterone propionate
type: MetaboliteLigand

rimexolone
in ch i key: QTTRZHGPGKRAFB-OOKHYKNYSA-N
in ch i: InChI=1S/C24H34O3/c1-6-20(27)24(5)14(2)11-18-17-8-7-15-12-16(25)9-10-22(15,3)21(17)19(26)13-23(18,24)4/h9-10,12,14,17-19,21,26H,6-8,11,13H2,1-5H3/t14-,17+,18+,19+,21-,22+,23+,24-/m1/s1
comment: Rimexolone is a corticosteroid.
iupac name: (8S,9S,10R,11S,13S,14S,16R,17S)-11-hydroxy-10,13,16,17-tetramethyl-17-propanoyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-3-one
xref: CHEMBL1200617
synonym: ORG-6216
synonym: Vexol®
approved: t
ligand name: rimexolone
type: MetaboliteLigand

rescinnamine
in ch i key: SZLZWPPUNLXJEA-QEGASFHISA-N
in ch i: InChI=1S/C35H42N2O9/c1-40-21-8-9-22-23-11-12-37-18-20-15-29(46-30(38)10-7-19-13-27(41-2)33(43-4)28(14-19)42-3)34(44-5)31(35(39)45-6)24(20)17-26(37)32(23)36-25(22)16-21/h7-10,13-14,16,20,24,26,29,31,34,36H,11-12,15,17-18H2,1-6H3/b10-7+/t20-,24+,26-,29-,31+,34+/m1/s1
comment: Rescinnamine is an angiotensin-converting enzyme (ACE) inhibitor. There is no information regarding approval for clinical use of this drug on the US FDA website. Other national approval agencies may have granted marketing authorisation.
iupac name: methyl (1R,15S,17R,18R,19S,20S)-6,18-dimethoxy-17-[(E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]oxy-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate
xref: CHEMBL1668
synonym: Moderil
synonym: Cinnasil
approved: t
ligand name: rescinnamine
type: NaturalProductLigand

quinestrol
in ch i key: PWZUUYSISTUNDW-VAFBSOEGSA-N
in ch i: InChI=1S/C25H32O2/c1-3-25(26)15-13-23-22-10-8-17-16-19(27-18-6-4-5-7-18)9-11-20(17)21(22)12-14-24(23,25)2/h1,9,11,16,18,21-23,26H,4-8,10,12-15H2,2H3/t21-,22-,23+,24+,25+/m1/s1
comment: Quinestrol is a synthetic estrogen.
iupac name: (8R,9S,13S,14S,17R)-3-cyclopentyloxy-17-ethynyl-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-ol
xref: CHEMBL1201165
synonym: Estrovis®
synonym: W-3566
approved: t
ligand name: quinestrol
type: NaturalProductLigand

prednisone
in ch i key: XOFYZVNMUHMLCC-ZPOLXVRWSA-N
in ch i: InChI=1S/C21H26O5/c1-19-7-5-13(23)9-12(19)3-4-14-15-6-8-21(26,17(25)11-22)20(15,2)10-16(24)18(14)19/h5,7,9,14-15,18,22,26H,3-4,6,8,10-11H2,1-2H3/t14-,15-,18+,19-,20-,21-/m0/s1
comment: Prednisone is a corticosteroid.
iupac name: (8S,9S,10R,13S,14S,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-6,7,8,9,12,14,15,16-octahydrocyclopenta[a]phenanthrene-3,11-dione
xref: CHEMBL635
synonym: Rayos
synonym: Cortan
synonym: Orasone
synonym: Paracort
synonym: Deltasone
synonym: Fernisone
synonym: Servisone
synonym: Delta-Dome
synonym: Meticorten
synonym: Prednisone
synonym: Sterapred®
synonym: Lodotra®
approved: t
ligand name: prednisone
type: MetaboliteLigand

pentoxifylline
canonical SMILES: CC(=O)CCCCn1c(=O)c2n(C)cnc2n(c1=O)C
isomeric SMILES: CC(=O)CCCCn1c(=O)c2n(C)cnc2n(c1=O)C
in ch i key: BYPFEZZEUUWMEJ-UHFFFAOYSA-N
in ch i: InChI=1S/C13H18N4O3/c1-9(18)6-4-5-7-17-12(19)10-11(14-8-15(10)2)16(3)13(17)20/h8H,4-7H2,1-3H3
comment: Pentoxifylline is a methylated xanthine derivative drug which acts as a competitive non-selective phosphodiesterase (PDE) inhibitor <Reference id=23975/>.
iupac name: 3,7-dimethyl-1-(5-oxohexyl)-2,3,6,7-tetrahydro-1H-purine-2,6-dione
xref: CHEMBL628
synonym: BL-191
synonym: Pentoxil
synonym: Trental®
approved: t
ligand name: pentoxifylline
type: SyntheticOrganicLigand

oxymorphone
canonical SMILES: O=C1CCC2(C34C1Oc1c4c(CC2N(CC3)C)ccc1O)O
in ch i key: UQCNKQCJZOAFTQ-ISWURRPUSA-N
in ch i: InChI=1S/C17H19NO4/c1-18-7-6-16-13-9-2-3-10(19)14(13)22-15(16)11(20)4-5-17(16,21)12(18)8-9/h2-3,12,15,19,21H,4-8H2,1H3/t12-,15+,16+,17-/m1/s1
comment: Oxymorphone is an opioid drug.
iupac name: (4R,4aS,7aR,12bS)-4a,9-dihydroxy-3-methyl-2,4,5,6,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinoline-7-one
xref: CHEMBL963
synonym: Opana Er
synonym: Numorphan
synonym: Opana®
synonym: oxymorphone hydrochloride
approved: t
ligand name: oxymorphone
type: NaturalProductLigand

oxycodone
in ch i key: BRUQQQPBMZOVGD-XFKAJCMBSA-N
in ch i: InChI=1S/C18H21NO4/c1-19-8-7-17-14-10-3-4-12(22-2)15(14)23-16(17)11(20)5-6-18(17,21)13(19)9-10/h3-4,13,16,21H,5-9H2,1-2H3/t13-,16+,17+,18-/m1/s1
comment: Oxycodone is an opioid drug.
iupac name: (4R,4aS,7aR,12bS)-4a-hydroxy-9-methoxy-3-methyl-2,4,5,6,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinoline-7-one
xref: CHEMBL656
synonym: Oxecta
synonym: Oxycontin
synonym: Roxicodone®
synonym: oxycodone hydrochloride
approved: t
ligand name: oxycodone
type: NaturalProductLigand

oxandrolone
canonical SMILES: O=C1OCC2(C(C1)CCC1C2CCC2(C1CCC2(C)O)C)C
in ch i key: QSLJIVKCVHQPLV-PEMPUTJUSA-N
in ch i: InChI=1S/C19H30O3/c1-17-11-22-16(20)10-12(17)4-5-13-14(17)6-8-18(2)15(13)7-9-19(18,3)21/h12-15,21H,4-11H2,1-3H3/t12-,13+,14-,15-,17-,18-,19-/m0/s1
comment: Oxandrolone is a synthetic anabolic steroid.
iupac name: (1S,3aS,3bR,5aS,9aS,9bS,11aS)-1-hydroxy-1,9a,11a-trimethyl-2,3,3a,3b,4,5,5a,6,9,9b,10,11-dodecahydroindeno[4,5-h]isochromen-7-one
xref: CHEMBL1200436
synonym: Oxandrin
synonym: Oxandrolone
synonym: SC-11585
synonym: Anavar®
approved: t
ligand name: oxandrolone
type: MetaboliteLigand

norgestimate
in ch i key: KIQQMECNKUGGKA-NMYWJIRASA-N
in ch i: InChI=1S/C23H31NO3/c1-4-22-12-10-19-18-9-7-17(24-26)14-16(18)6-8-20(19)21(22)11-13-23(22,5-2)27-15(3)25/h2,14,18-21,26H,4,6-13H2,1,3H3/b24-17+/t18-,19+,20+,21-,22-,23-/m0/s1
comment: Norgestimate is an acetylated progestin (synthelic progesterone-like compound). It is converted to the primary active metabolite norelgestromin (17-deacetylnorgestimate or levonorgestrel 3-oxime) in vivo. 17-deacetylnorgestimate does not cause the androgenic side effects associated with other 19-nortestosterone progestins.
iupac name: [(3E,8R,9S,10R,13S,14S,17R)-13-ethyl-17-ethynyl-3-hydroxyimino-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-yl] acetate
xref: CHEMBL1200934
synonym: ORF-10131
synonym: RWJ-10131
synonym: dexnorgestrel
approved: t
ligand name: norgestimate
type: MetaboliteLigand

nelarabine
canonical SMILES: OCC1OC(C(C1O)O)n1cnc2c1[nH]c(=N)nc2OC
in ch i key: IXOXBSCIXZEQEQ-UHTZMRCNSA-N
in ch i: InChI=1S/C11H15N5O5/c1-20-9-5-8(14-11(12)15-9)16(3-13-5)10-7(19)6(18)4(2-17)21-10/h3-4,6-7,10,17-19H,2H2,1H3,(H2,12,14,15)/t4-,6-,7+,10-/m1/s1
comment: This compound is a prodrug. The active metabolite is its 5'-triphosphate, ara-GTP.
iupac name: (2R,3S,4S,5R)-2-(hydroxymethyl)-5-(2-imino-6-methoxy-3,9-dihydro-2H-purin-9-yl)oxolane-3,4-diol
xref: CHEMBL1201112
synonym: 506U78
synonym: MAY
synonym: Arranon®
synonym: Atriance®
approved: t
ligand name: nelarabine
type: SyntheticOrganicLigand

mitomycin C
in ch i key: NWIBSHFKIJFRCO-WUDYKRTCSA-N
in ch i: InChI=1S/C15H18N4O5/c1-5-9(16)12(21)8-6(4-24-14(17)22)15(23-2)13-7(18-13)3-19(15)10(8)11(5)20/h6-7,13,18H,3-4,16H2,1-2H3,(H2,17,22)/t6-,7+,13+,15-/m1/s1
comment: Mitomycin C is an antineoplastic drug, with DNA alkylating activity. It is one of the mitomycin family of compounds, isolated from Streptomyces caespitosus or Streptomyces lavendulae.
xref: CHEMBL105
synonym: Mutamycin
synonym: Mitozytrex
synonym: NSC-26980
synonym: mitomycin C
synonym: Mitosol®
approved: t
ligand name: mitomycin C
type: NaturalProductLigand

methylprednisolone
in ch i key: VHRSUDSXCMQTMA-PJHHCJLFSA-N
in ch i: InChI=1S/C22H30O5/c1-12-8-14-15-5-7-22(27,18(26)11-23)21(15,3)10-17(25)19(14)20(2)6-4-13(24)9-16(12)20/h4,6,9,12,14-15,17,19,23,25,27H,5,7-8,10-11H2,1-3H3/t12-,14-,15-,17-,19+,20-,21-,22-/m0/s1
comment: Methylprednisolone is a corticosteroid. Marketed formulations may contain methylprednisolone acetate (PubChem CID 5877). Methylprednisolone has been reported to activate the TRPC5 ion channel <Reference id=37288/>. Methylprednisolone-induced activation of TRPC5 is long lasting, reversible and sensitive to the TRPC5 inhibitor <Ligand id=10285/> <Reference id=37288/>.
iupac name: (6S,8S,9S,10R,11S,13S,14S,17R)-11,17-dihydroxy-17-(2-hydroxyacetyl)-6,10,13-trimethyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-3-one
xref: CHEMBL650
synonym: M-Predrol
synonym: Depmedalone
synonym: Depo-Medrol
synonym: Solu-Medrol
synonym: Medrol Acetate
synonym: Methylprednisolone
synonym: Medrol®
synonym: U-67590A
approved: t
ligand name: methylprednisolone
type: MetaboliteLigand

mestranol
canonical SMILES: C#CC1(O)CCC2C1(C)CCC1C2CCc2c1ccc(c2)OC
in ch i key: IMSSROKUHAOUJS-MJCUULBUSA-N
in ch i: InChI=1S/C21H26O2/c1-4-21(22)12-10-19-18-7-5-14-13-15(23-3)6-8-16(14)17(18)9-11-20(19,21)2/h1,6,8,13,17-19,22H,5,7,9-12H2,2-3H3/t17-,18-,19+,20+,21+/m1/s1
comment: Mestranol is the inactive prodrug of ethinylestradiol. Marketing authorisation is for a combined norethisterone/mestranol formulation.
iupac name: (8R,9S,13S,14S,17R)-17-ethynyl-3-methoxy-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-ol
xref: CHEMBL1201151
synonym: EE3-ME
approved: t
ligand name: mestranol
type: MetaboliteLigand

medrysone
in ch i key: GZENKSODFLBBHQ-ILSZZQPISA-N
in ch i: InChI=1S/C22H32O3/c1-12-9-15-17-6-5-16(13(2)23)22(17,4)11-19(25)20(15)21(3)8-7-14(24)10-18(12)21/h10,12,15-17,19-20,25H,5-9,11H2,1-4H3/t12-,15-,16+,17-,19-,20+,21-,22+/m0/s1
comment: Medrysone is a corticosteroid.
iupac name: (6S,8S,9S,10R,11S,13S,14S,17S)-17-acetyl-11-hydroxy-6,10,13-trimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
xref: CHEMBL1201173
synonym: HMS
synonym: U-8471
approved: t
ligand name: medrysone
type: MetaboliteLigand

loteprednol etabonate
in ch i key: DMKSVUSAATWOCU-HROMYWEYSA-N
in ch i: InChI=1S/C24H31ClO7/c1-4-30-21(29)32-24(20(28)31-13-25)10-8-17-16-6-5-14-11-15(26)7-9-22(14,2)19(16)18(27)12-23(17,24)3/h7,9,11,16-19,27H,4-6,8,10,12-13H2,1-3H3/t16-,17-,18-,19+,22-,23-,24-/m0/s1
comment: Loteprednol is a corticosteroid.
iupac name: chloromethyl (8S,9S,10R,11S,13S,14S,17R)-17-ethoxycarbonyloxy-11-hydroxy-10,13-dimethyl-3-oxo-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-17-carboxylate
xref: CHEMBL1200865
synonym: Inveltys®
synonym: Alrex
synonym: Lotemax®
synonym: P-5604
synonym: HGP-1
approved: t
ligand name: loteprednol etabonate
type: MetaboliteLigand

idarubicin
in ch i key: XDXDZDZNSLXDNA-TZNDIEGXSA-N
in ch i: InChI=1S/C26H27NO9/c1-10-21(29)15(27)7-17(35-10)36-16-9-26(34,11(2)28)8-14-18(16)25(33)20-19(24(14)32)22(30)12-5-3-4-6-13(12)23(20)31/h3-6,10,15-17,21,29,32-34H,7-9,27H2,1-2H3/t10-,15-,16-,17-,21+,26-/m0/s1
comment: Idarubicin is an anthracycline type antineoplastic drug.
iupac name: (7S,9S)-9-acetyl-7-{[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy}-6,9,11-trihydroxy-5,7,8,9,10,12-hexahydrotetracene-5,12-dione
xref: CHEMBL1117
synonym: IMI-30
synonym: Idamycin Pfs
synonym: Idarubicin Hydrochloride
synonym: Idarubicin Hydrochloride Pfs
synonym: Zavedos®
synonym: Idamycin®
approved: t
ligand name: idarubicin
type: NaturalProductLigand

hydromorphone
canonical SMILES: O=C1CCC2C34C1Oc1c4c(CC2N(CC3)C)ccc1O
in ch i key: WVLOADHCBXTIJK-YNHQPCIGSA-N
in ch i: InChI=1S/C17H19NO3/c1-18-7-6-17-10-3-5-13(20)16(17)21-15-12(19)4-2-9(14(15)17)8-11(10)18/h2,4,10-11,16,19H,3,5-8H2,1H3/t10-,11+,16-,17-/m0/s1
comment: Hydromorphone is an opioid receptor agonist.
iupac name: (4R,4aR,7aR,12bS)-9-hydroxy-3-methyl-1,2,4,4a,5,6,7a,13-octahydro-4,12-methanobenzofuro[3,2-e]isoquinoline-7-one
xref: CHEMBL398707
synonym: Exalgo
synonym: Dilaudid-Hp
synonym: Palladone®
synonym: Dilaudid®
synonym: hydromorphone hydrochloride
approved: t
ligand name: hydromorphone
type: NaturalProductLigand

hydrocodone
canonical SMILES: COc1ccc2c3c1OC1C43CCN(C(C2)C4CCC1=O)C
in ch i key: LLPOLZWFYMWNKH-CMKMFDCUSA-N
in ch i: InChI=1S/C18H21NO3/c1-19-8-7-18-11-4-5-13(20)17(18)22-16-14(21-2)6-3-10(15(16)18)9-12(11)19/h3,6,11-12,17H,4-5,7-9H2,1-2H3/t11-,12+,17-,18-/m0/s1
comment: Hydrocodone is an opioid receptor agonist.
iupac name: (4R,4aR,7aR,12bS)-9-methoxy-3-methyl-1,2,4,4a,5,6,7a,13-octahydro-4,12-methanobenzofuro[3,2-e]isoquinoline-7-one
xref: CHEMBL1457
synonym: dicodid
synonym: mercodinone
synonym: Zohydro®
synonym: Hycodan
synonym: Robidone
approved: t
ligand name: hydrocodone
type: NaturalProductLigand

desoximetasone
in ch i key: VWVSBHGCDBMOOT-IIEHVVJPSA-N
in ch i: InChI=1S/C22H29FO4/c1-12-8-16-15-5-4-13-9-14(25)6-7-21(13,3)22(15,23)18(27)10-20(16,2)19(12)17(26)11-24/h6-7,9,12,15-16,18-19,24,27H,4-5,8,10-11H2,1-3H3/t12-,15+,16+,18+,19-,20+,21+,22+/m1/s1
comment: Desoximetasone is a corticosteroid.
iupac name: (8S,9R,10S,11S,13S,14S,16R,17S)-9-fluoro-11-hydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-7,8,11,12,14,15,16,17-octahydro-6H-cyclopenta[a]phenanthren-3-one
xref: CHEMBL1766
synonym: R-2113
synonym: HOE-304
synonym: A-41-304
synonym: Topicort Lp
synonym: Desoximetasone
synonym: Topicort®
approved: t
ligand name: desoximetasone
type: MetaboliteLigand

fluticasone propionate
in ch i key: WMWTYOKRWGGJOA-CENSZEJFSA-N
in ch i: InChI=1S/C25H31F3O5S/c1-5-20(31)33-25(21(32)34-12-26)13(2)8-15-16-10-18(27)17-9-14(29)6-7-22(17,3)24(16,28)19(30)11-23(15,25)4/h6-7,9,13,15-16,18-19,30H,5,8,10-12H2,1-4H3/t13-,15+,16+,18+,19+,22+,23+,24+,25+/m1/s1
comment: Fluticasone propionate is a corticosteroid, high affinity and selective glucocorticoid receptor agonist.
iupac name: [(6S,8S,9R,10S,11S,13S,14S,16R,17R)-6,9-difluoro-17-(fluoromethylsulfanylcarbonyl)-11-hydroxy-10,13,16-trimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl] propanoate
xref: CHEMBL1473
synonym: ArmonAir RespiClickTM
synonym: CCI-18781
synonym: Flonase
synonym: Cutivate
synonym: Flovent Hfa
synonym: Flovent Diskus 50
synonym: Flovent Diskus 100
synonym: Flovent Diskus 250
synonym: Flovent®
synonym: Advair Diskus®
approved: t
ligand name: fluticasone propionate
type: SyntheticOrganicLigand

fluorometholone
in ch i key: FAOZLTXFLGPHNG-KNAQIMQKSA-N
in ch i: InChI=1S/C22H29FO4/c1-12-9-17-15-6-8-21(27,13(2)24)20(15,4)11-18(26)22(17,23)19(3)7-5-14(25)10-16(12)19/h5,7,10,12,15,17-18,26-27H,6,8-9,11H2,1-4H3/t12-,15-,17-,18-,19-,20-,21-,22-/m0/s1
comment: Fluorometholone is a corticosteroid.
iupac name: (6S,8S,9R,10S,11S,13S,14S,17R)-17-acetyl-9-fluoro-11,17-dihydroxy-6,10,13-trimethyl-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-3-one
xref: CHEMBL1200600
synonym: Oxylone
synonym: Fluor-Op
synonym: Fml Forte
synonym: Flarex®
synonym: FML®
approved: t
ligand name: fluorometholone
type: SyntheticOrganicLigand

fluocinonide
in ch i key: WJOHZNCJWYWUJD-IUGZLZTKSA-N
in ch i: InChI=1S/C26H32F2O7/c1-13(29)33-12-20(32)26-21(34-22(2,3)35-26)10-15-16-9-18(27)17-8-14(30)6-7-23(17,4)25(16,28)19(31)11-24(15,26)5/h6-8,15-16,18-19,21,31H,9-12H2,1-5H3/t15-,16-,18-,19-,21+,23-,24-,25-,26+/m0/s1
comment: Fluocinonide is a corticosteroid.
xref: CHEMBL1501
synonym: Vanos
synonym: Lidex-E
synonym: Fluocinonide Emulsified Base
synonym: Lidex®
synonym: Fluonex®
synonym: Lonide
synonym: Lyderm
approved: t
ligand name: fluocinonide
type: SyntheticOrganicLigand

BrP-LPA
in ch i key: HLVKVWDSLLFMSX-OYKVQYDMSA-N
in ch i: InChI=1S/C20H40BrO6P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-20(23)27-17-18(22)16-19(21)28(24,25)26/h18-19,22H,2-17H2,1H3,(H2,24,25,26)/t18-,19?/m0/s1
comment: Reference <Reference id=11932/> specifies that this compound is a racemic mixture, outlined in the paper as being comprised of stereoisomers syn- and anti- BrP-LPA (compounds 1a and 1b respectively). The configuration of the bond to the bromine atom determines and stereochemistry of the compound, and we do not specify an individual isomer here therefore this ligand entry represents the mixture.
iupac name: [(3S)-1-bromo-4-hexadecanoyloxy-3-hydroxybutyl]phosphonic acid
synonym: α-bromomethylene phosphonate
approved: f
ligand name: BrP-LPA
type: SyntheticOrganicLigand

fluocinolone acetonide
in ch i key: FEBLZLNTKCEFIT-VSXGLTOVSA-N
in ch i: InChI=1S/C24H30F2O6/c1-20(2)31-19-9-13-14-8-16(25)15-7-12(28)5-6-21(15,3)23(14,26)17(29)10-22(13,4)24(19,32-20)18(30)11-27/h5-7,13-14,16-17,19,27,29H,8-11H2,1-4H3/t13-,14-,16-,17-,19+,21-,22-,23-,24+/m0/s1
comment: Fluocinolone acetonide is a corticosteroid.
xref: CHEMBL989
synonym: Iluvien®
synonym: Fluocet
synonym: Fluonid
synonym: Dermotic
synonym: Fluotrex
synonym: Retisert
synonym: Synalar-Hp
synonym: Derma-Smoothe/Fs
synonym: Capex®
synonym: Synalar®
approved: t
ligand name: fluocinolone acetonide
type: SyntheticOrganicLigand

flunisolide
in ch i key: XSFJVAJPIHIPKU-XWCQMRHXSA-N
in ch i: InChI=1S/C24H31FO6/c1-21(2)30-19-9-14-13-8-16(25)15-7-12(27)5-6-22(15,3)20(13)17(28)10-23(14,4)24(19,31-21)18(29)11-26/h5-7,13-14,16-17,19-20,26,28H,8-11H2,1-4H3/t13-,14-,16-,17-,19+,20+,22-,23-,24+/m0/s1
comment: Flunisolide is a corticosteroid.
xref: CHEMBL1512
synonym: Nasarel
synonym: Nasalide
synonym: Aerospan hfa
synonym: AeroBid®
synonym: RS-3999
synonym: Syntaris
approved: t
ligand name: flunisolide
type: SyntheticOrganicLigand

flumethasone pivalate
in ch i key: JWRMHDSINXPDHB-OJAGFMMFSA-N
in ch i: InChI=1S/C27H36F2O6/c1-14-9-16-17-11-19(28)18-10-15(30)7-8-24(18,5)26(17,29)20(31)12-25(16,6)27(14,34)21(32)13-35-22(33)23(2,3)4/h7-8,10,14,16-17,19-20,31,34H,9,11-13H2,1-6H3/t14-,16+,17+,19+,20+,24+,25+,26+,27+/m1/s1
comment: Flumethasone pivalate is a corticosteroid.
iupac name: [2-[(6S,8S,9R,10S,11S,13S,14S,16R,17R)-6,9-difluoro-11,17-dihydroxy-10,13,16-trimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl]-2-oxoethyl] 2,2-dimethylpropanoate
xref: CHEMBL1200877
synonym: Locorten®
synonym: Locacorten
approved: t
ligand name: flumethasone pivalate
type: SyntheticOrganicLigand

famotidine
canonical SMILES: NC(=Nc1scc(n1)CSCCC(=NS(=O)(=O)N)N)N
isomeric SMILES: NC(=Nc1scc(n1)CSCC/C(=N/S(=O)(=O)N)/N)N
in ch i key: XUFQPHANEAPEMJ-UHFFFAOYSA-N
in ch i: InChI=1S/C8H15N7O2S3/c9-6(15-20(12,16)17)1-2-18-3-5-4-19-8(13-5)14-7(10)11/h4H,1-3H2,(H2,9,15)(H2,12,16,17)(H4,10,11,13,14)
comment: Famotidine is a histamine H2 receptor antagonist. The drug is poorly soluble in the low pH of the stomach so suffers from poor bioavailability. Low dose (10-20 mg) famotidine is available over-the-counter in some countries. Marketing of a combination of famotidine with antacids magnesium hydroxide and calcium carbonate (Pepcidtwo®) has been officially discontinued in the UK (2015).
iupac name: 3-[[2-(diaminomethylideneamino)-1,3-thiazol-4-yl]methylsulfanyl]-N'-sulfamoylpropanimidamide
xref: CHEMBL902
synonym: Fluxid
synonym: Pepcid Ac
synonym: Pepcid Rpd
synonym: Pepcid®
synonym: MK-208
synonym: Gaster®
synonym: Pepcidine
approved: t
ligand name: famotidine
type: SyntheticOrganicLigand

exemestane
in ch i key: BFYIZQONLCFLEV-DAELLWKTSA-N
in ch i: InChI=1S/C20H24O2/c1-12-10-14-15-4-5-18(22)20(15,3)9-7-16(14)19(2)8-6-13(21)11-17(12)19/h6,8,11,14-16H,1,4-5,7,9-10H2,2-3H3/t14-,15-,16-,19+,20-/m0/s1
comment: Exemestane is a steroidal aromatase inhibitor.
iupac name: (8R,9S,10R,13S,14S)-10,13-dimethyl-6-methylidene-7,8,9,11,12,14,15,16-octahydrocyclopenta[a]phenanthrene-3,17-dione
xref: CHEMBL1200374
synonym: Aromasin®
synonym: FCE-24304
approved: t
ligand name: exemestane
type: MetaboliteLigand

ethynodiol diacetate
in ch i key: ONKUMRGIYFNPJW-KIEAKMPYSA-N
in ch i: InChI=1S/C24H32O4/c1-5-24(28-16(3)26)13-11-22-21-8-6-17-14-18(27-15(2)25)7-9-19(17)20(21)10-12-23(22,24)4/h1,14,18-22H,6-13H2,2-4H3/t18-,19-,20+,21+,22-,23-,24-/m0/s1
comment: This compound is a progestin.
iupac name: [(3S,8R,9S,10R,13S,14S,17R)-17-acetyloxy-17-ethynyl-13-methyl-2,3,6,7,8,9,10,11,12,14,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate
xref: CHEMBL1200624
synonym: SC-11800
synonym: Continuin®
synonym: Femulen®
synonym: Luteonorm
synonym: Luto-Metrodiol
synonym: Metrodiol
approved: t
ligand name: ethynodiol diacetate
type: MetaboliteLigand

ethinylestradiol
canonical SMILES: C#CC1(O)CCC2C1(C)CCC1C2CCc2c1ccc(c2)O
in ch i key: BFPYWIDHMRZLRN-SLHNCBLASA-N
in ch i: InChI=1S/C20H24O2/c1-3-20(22)11-9-18-17-6-4-13-12-14(21)5-7-15(13)16(17)8-10-19(18,20)2/h1,5,7,12,16-18,21-22H,4,6,8-11H2,2H3/t16-,17-,18+,19+,20+/m1/s1
comment: Ethinylestradiol is contained in a large number of combined oral contraceptive formulations and HRT medications. Use of ethinylestradiol, unapposed by a progestin, increases the risk of endometrial cancer.
iupac name: (8R,9S,13S,14S,17R)-17-ethynyl-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-3,17-diol
xref: CHEMBL691
synonym: ethinyl estradiol
synonym: Estinyl
synonym: Lynoral
synonym: Feminone
synonym: Etinestryl
synonym: Follicoral
synonym: 17α-ethynylestradiol
approved: t
ligand name: ethinylestradiol
type: MetaboliteLigand

dyphylline
canonical SMILES: OCC(Cn1cnc2c1c(=O)n(C)c(=O)n2C)O
isomeric SMILES: OCC(Cn1cnc2c1c(=O)n(C)c(=O)n2C)O
in ch i key: KSCFJBIXMNOVSH-UHFFFAOYSA-N
in ch i: InChI=1S/C10H14N4O4/c1-12-8-7(9(17)13(2)10(12)18)14(5-11-8)3-6(16)4-15/h5-6,15-16H,3-4H2,1-2H3
comment: Dyphylline is a bronchodilator and vasodilator.
iupac name: 7-(2,3-dihydroxypropyl)-1,3-dimethyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione
xref: CHEMBL1752
synonym: Lufyllin
synonym: Dilor-400
synonym: Neothylline
synonym: Dilor®
approved: t
ligand name: dyphylline
type: MetaboliteLigand

doxorubicin
in ch i key: AOJJSUZBOXZQNB-TZSSRYMLSA-N
in ch i: InChI=1S/C27H29NO11/c1-10-22(31)13(28)6-17(38-10)39-15-8-27(36,16(30)9-29)7-12-19(15)26(35)21-20(24(12)33)23(32)11-4-3-5-14(37-2)18(11)25(21)34/h3-5,10,13,15,17,22,29,31,33,35-36H,6-9,28H2,1-2H3/t10-,13-,15-,17-,22+,27-/m0/s1
comment: Doxorubicin is an anthracycline type anti-neoplastic drug.
iupac name: (8S,10S)-10-{[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy}-6,8,11-trihydroxy-8-(2-hydroxyacetyl)-1-methoxy-5,7,8,9,10,12-hexahydrotetracene-5,12-dione
xref: CHEMBL53463
synonym: Caelyx® (liposomal doxorubicin)
synonym: Rubex
synonym: Adriblastina
synonym: Adriamycin Pfs
synonym: Adriamycin Rdf
synonym: Doxil®
synonym: doxorubicin hydrochloride
synonym: Adriamycin®
approved: t
ligand name: doxorubicin
type: NaturalProductLigand

diflorasone diacetate
in ch i key: BOBLHFUVNSFZPJ-JOYXJVLSSA-N
in ch i: InChI=1S/C26H32F2O7/c1-13-8-17-18-10-20(27)19-9-16(31)6-7-23(19,4)25(18,28)21(32)11-24(17,5)26(13,35-15(3)30)22(33)12-34-14(2)29/h6-7,9,13,17-18,20-21,32H,8,10-12H2,1-5H3/t13-,17-,18-,20-,21-,23-,24-,25-,26-/m0/s1
comment: Diflorasone is a corticosteroid.
iupac name: [2-[(6S,8S,9R,10S,11S,13S,14S,16S,17R)-17-acetyloxy-6,9-difluoro-11-hydroxy-10,13,16-trimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl]-2-oxoethyl] acetate
xref: CHEMBL1200545
synonym: Florone
synonym: Florone E
synonym: Psorcon E
synonym: Diflorasone Diacetate
synonym: Psorcon®
synonym: U-34865
approved: t
ligand name: diflorasone diacetate
type: SyntheticOrganicLigand

desonide
in ch i key: WBGKWQHBNHJJPZ-LECWWXJVSA-N
in ch i: InChI=1S/C24H32O6/c1-21(2)29-19-10-16-15-6-5-13-9-14(26)7-8-22(13,3)20(15)17(27)11-23(16,4)24(19,30-21)18(28)12-25/h7-9,15-17,19-20,25,27H,5-6,10-12H2,1-4H3/t15-,16-,17-,19+,20+,22-,23-,24+/m0/s1
comment: Desonide is a corticosteroid.
xref: CHEMBL1201109
synonym: D-2083
synonym: Verdeso
synonym: Desonate
synonym: Desonide
synonym: Desowen®
approved: t
ligand name: desonide
type: NaturalProductLigand

desogestrel
canonical SMILES: CCC12CC(=C)C3C(C1CCC2(O)C#C)CCC1=CCCCC31
in ch i key: RPLCPCMSCLEKRS-BPIQYHPVSA-N
in ch i: InChI=1S/C22H30O/c1-4-21-14-15(3)20-17-9-7-6-8-16(17)10-11-18(20)19(21)12-13-22(21,23)5-2/h2,8,17-20,23H,3-4,6-7,9-14H2,1H3/t17-,18-,19-,20+,21-,22-/m0/s1
comment: Desogestrel is a progestin (synthetic progesterone-like agent) widely used in third-generation hormonal contraceptives. Desogestrel is converted to <Ligand id=7590/> (3-ketodesogestrel) in vivo. There has been controversy surrounding reports that third-generation oral contraceptives containing desogestrel pose a risk of dangerous blood clots compared to older second-generation oral contraceptives.
iupac name: (8S,9S,10R,13S,14S,17R)-13-ethyl-17-ethynyl-11-methylidene-1,2,3,6,7,8,9,10,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-ol
xref: CHEMBL1533
synonym: ORG-2969
approved: t
ligand name: desogestrel
type: SyntheticOrganicLigand

deserpidine
in ch i key: CVBMAZKKCSYWQR-WCGOZPBSSA-N
in ch i: InChI=1S/C32H38N2O8/c1-37-24-12-17(13-25(38-2)29(24)39-3)31(35)42-26-14-18-16-34-11-10-20-19-8-6-7-9-22(19)33-28(20)23(34)15-21(18)27(30(26)40-4)32(36)41-5/h6-9,12-13,18,21,23,26-27,30,33H,10-11,14-16H2,1-5H3/t18-,21+,23-,26-,27+,30+/m1/s1
comment: Deserpidine is chemically related to <Ligand id=4823/>.
iupac name: methyl (1R,15S,17R,18R,19S,20S)-18-methoxy-17-(3,4,5-trimethoxybenzoyl)oxy-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate
xref: CHEMBL1200515
synonym: Harmonyl®
synonym: recanescin
approved: t
ligand name: deserpidine
type: NaturalProductLigand

daunorubicin
in ch i key: STQGQHZAVUOBTE-VGBVRHCVSA-N
in ch i: InChI=1S/C27H29NO10/c1-10-22(30)14(28)7-17(37-10)38-16-9-27(35,11(2)29)8-13-19(16)26(34)21-20(24(13)32)23(31)12-5-4-6-15(36-3)18(12)25(21)33/h4-6,10,14,16-17,22,30,32,34-35H,7-9,28H2,1-3H3/t10-,14-,16-,17-,22+,27-/m0/s1
comment: Daunorubicin is an anthracycline class chemotherapeutic for cancer treatment. Daunorubicin is on the World Health Organisation's List of Essential Medicines. Click here to access the pdf version of the WHO's 21st Essential Medicines list (2019).
iupac name: (8S,10S)-8-acetyl-10-{[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy}-6,8,11-trihydroxy-1-methoxy-5,7,8,9,10,12-hexahydrotetracene-5,12-dione
xref: CHEMBL178
synonym: daunorubicin hydrochloride
synonym: Daunoxome
synonym: Cerubidine®
synonym: FI-6339
synonym: NDC-0082-4155
synonym: RP-13057
synonym: daunomycin cerubidine
synonym: daunomycin
approved: t
ligand name: daunorubicin
type: NaturalProductLigand

clobetasol propionate
in ch i key: CBGUOGMQLZIXBE-XGQKBEPLSA-N
in ch i: InChI=1S/C25H32ClFO5/c1-5-21(31)32-25(20(30)13-26)14(2)10-18-17-7-6-15-11-16(28)8-9-22(15,3)24(17,27)19(29)12-23(18,25)4/h8-9,11,14,17-19,29H,5-7,10,12-13H2,1-4H3/t14-,17-,18-,19-,22-,23-,24-,25-/m0/s1
comment: Clobetasol is a highly active, topical corticosteroid.
iupac name: [(8S,9R,10S,11S,13S,14S,16S,17R)-17-(2-chloroacetyl)-9-fluoro-11-hydroxy-10,13,16-trimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl] propanoate
xref: CHEMBL1159650
synonym: GR 2/925
synonym: CCI-4725
synonym: OLUX
synonym: Cormax
synonym: Olux E
synonym: Embeline
synonym: Embeline E
synonym: Temovate E
synonym: Clobex®
synonym: Temovate®
synonym: Dermovate®
approved: t
ligand name: clobetasol propionate
type: SyntheticOrganicLigand

betamethasone
in ch i key: UREBDLICKHMUKA-DVTGEIKXSA-N
in ch i: InChI=1S/C22H29FO5/c1-12-8-16-15-5-4-13-9-14(25)6-7-19(13,2)21(15,23)17(26)10-20(16,3)22(12,28)18(27)11-24/h6-7,9,12,15-17,24,26,28H,4-5,8,10-11H2,1-3H3/t12-,15-,16-,17-,19-,20-,21-,22-/m0/s1
comment: Marketed medications may contain dipropionate (eg Diprosone® and Diprolene®), sodium phosphate (eg Bentelan®) or valerate (eg Betnovate® and Celestone®) formulations.
iupac name: (8S,9R,10S,11S,13S,14S,16S,17R)-9-fluoro-11,17-dihydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-3-one
xref: CHEMBL632
synonym: SCH-4831
synonym: Betaderm
synonym: Betatrex
synonym: Taclonex
synonym: Valisone
synonym: Uticort
synonym: Beta-Val
synonym: Betasolan
synonym: Celestone
synonym: Alphatrex
approved: t
ligand name: betamethasone
type: MetaboliteLigand

amcinonide
in ch i key: ILKJAFIWWBXGDU-MOGDOJJUSA-N
in ch i: InChI=1S/C28H35FO7/c1-16(30)34-15-22(33)28-23(35-26(36-28)9-4-5-10-26)13-20-19-7-6-17-12-18(31)8-11-24(17,2)27(19,29)21(32)14-25(20,28)3/h8,11-12,19-21,23,32H,4-7,9-10,13-15H2,1-3H3/t19-,20-,21-,23+,24-,25-,27-,28+/m0/s1
comment: A topically applied corticosteroid.
xref: CHEMBL1200732
synonym: CL-34699
synonym: Amcinonide
synonym: Cyclocort®
approved: t
ligand name: amcinonide
type: SyntheticOrganicLigand

beclometasone
in ch i key: NBMKJKDGKREAPL-DVTGEIKXSA-N
in ch i: InChI=1S/C22H29ClO5/c1-12-8-16-15-5-4-13-9-14(25)6-7-19(13,2)21(15,23)17(26)10-20(16,3)22(12,28)18(27)11-24/h6-7,9,12,15-17,24,26,28H,4-5,8,10-11H2,1-3H3/t12-,15-,16-,17-,19-,20-,21-,22-/m0/s1
comment: Beclometasone is the active form of the prodrug beclometasone dipropionate.
iupac name: (8S,9R,10S,11S,13S,14S,16S,17R)-9-chloro-11,17-dihydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-3-one
xref: CHEMBL1586
synonym: beclomethasone
synonym: SCH-18020W
synonym: Beconase
synonym: Vancenase
synonym: Qnasl
approved: t
ligand name: beclometasone
type: SyntheticOrganicLigand

NQN-1
canonical SMILES: O=C(c1ccccc1)NC1=CC(=O)c2c(C1=O)cccc2
isomeric SMILES: O=C(c1ccccc1)NC1=CC(=O)c2c(C1=O)cccc2
in ch i key: BIVQBWSIGJFXLF-UHFFFAOYSA-N
in ch i: InChI=1S/C17H11NO3/c19-15-10-14(16(20)13-9-5-4-8-12(13)15)18-17(21)11-6-2-1-3-7-11/h1-10H,(H,18,21)
comment: This compound is already used to inhibit NF-κB activation, but is also reported to be a selective inhibitor of HDAC6 <Reference id=23904/>.
iupac name: N-(1,4-dioxonaphthalen-2-yl)benzamide
xref: CHEMBL1717890
synonym: PPM-18
synonym: NSC 73233
approved: f
ligand name: NQN-1
type: SyntheticOrganicLigand

compound 16 [PMID: 20947351]
in ch i key: YKINZQJOQFMNPU-AWEZNQCLSA-N
in ch i: InChI=1S/C18H33N3O5/c1-18(2,3)26-17(24)20-14(11-5-4-6-12-15(22)21-25)16(23)19-13-9-7-8-10-13/h13-14,25H,4-12H2,1-3H3,(H,19,23)(H,20,24)(H,21,22)/t14-/m0/s1
comment: This compound is a selective HDAC6 inhibitor, and is approximately 55 times more selective for HDAC6 compared to HDAC1 <Reference id=23903/>.
iupac name: tert-butyl N-[(2S)-1-(cyclopentylamino)-8-(hydroxyamino)-1,8-dioxooctan-2-yl]carbamate
xref: CHEMBL1289931
approved: f
ligand name: compound 16 [PMID: 20947351]
type: SyntheticOrganicLigand

compound 7d [PMID: 19111466]
in ch i key: HBEDNENASUYMPO-LJQANCHMSA-N
in ch i: InChI=1S/C21H19N3O3S/c25-20(23-27)15-9-7-14(8-10-15)13-24-18-6-2-1-5-17(18)22-21(26)19(24)12-16-4-3-11-28-16/h1-11,19,27H,12-13H2,(H,22,26)(H,23,25)/t19-/m1/s1
comment: This compound is a selective inhibitor of HDAC6 <Reference id=23905/>.
iupac name: N-hydroxy-4-[[(2R)-3-oxo-2-(thiophen-2-ylmethyl)-2,4-dihydroquinoxalin-1-yl]methyl]benzamide
xref: CHEMBL518957
approved: f
ligand name: compound 7d [PMID: 19111466]
type: SyntheticOrganicLigand

sucralfate
in ch i key: MNQYNQBOVCBZIQ-JQOFMKNESA-A
in ch i: InChI=1S/C11H20O35S8.8Al.16H2O/c12-47(13,14)36-1-3-4(41-49(18,19)20)5(42-50(21,22)23)6(43-51(24,25)26)9(38-3)39-11(2-37-48(15,16)17)8(45-53(30,31)32)7(44-52(27,28)29)10(40-11)46-54(33,34)35;;;;;;;;;;;;;;;;;;;;;;;;/h3-10H,1-2H2,(H,12,13,14)(H,15,16,17)(H,18,19,20)(H,21,22,23)(H,24,25,26)(H,27,28,29)(H,30,31,32)(H,33,34,35);;;;;;;;;16*1H2/q;8*+3;;;;;;;;;;;;;;;;/p-24/t3-,4-,5+,6-,7+,8+,9+,10-,11-;;;;;;;;;;;;;;;;;;;;;;;;/m1......................../s1
comment: Sucralfate is a complex of sucrose, sulfate and aluminum which is basic in nature and has an overall negative charge. Note that this is a complicated chemical complex. Different chemical databases represent this compound in different ways, all of which are valid. The ChEMBL compound is represented by the entry CHEMBL2367706, with separate aluminium hydroxide ions, whereas the structure we show has these ions in association with the sulphites on the core disaccharide sugar. PubChem CID 70789197 also represents the aluminium hydroxide groups in a different way.
synonym: Carafate®
synonym: Ulcerlmin
synonym: Sucramal
synonym: Sucralcoat
synonym: Antepsin®
approved: t
ligand name: sucralfate
type: SyntheticOrganicLigand

aminoglutethimide
canonical SMILES: CCC1(CCC(=O)NC1=O)c1ccc(cc1)N
isomeric SMILES: CCC1(CCC(=O)NC1=O)c1ccc(cc1)N
in ch i key: ROBVIMPUHSLWNV-UHFFFAOYSA-N
in ch i: InChI=1S/C13H16N2O2/c1-2-13(8-7-11(16)15-12(13)17)9-3-5-10(14)6-4-9/h3-6H,2,7-8,14H2,1H3,(H,15,16,17)
comment: Aminoglutethimide is an aromatase (CYP19A1) and steroid 11β-hydroxylase (CYP11A1) inhibitor.
iupac name: 3-(4-aminophenyl)-3-ethylpiperidine-2,6-dione
xref: CHEMBL488
synonym: Cytadren®
approved: t
ligand name: aminoglutethimide
type: SyntheticOrganicLigand

isosorbide dinitrate
canonical SMILES: [O-][N+](=O)OC1COC2C1OCC2O[N+](=O)[O-]
in ch i key: MOYKHGMNXAOIAT-JGWLITMVSA-N
in ch i: InChI=1S/C6H8N2O8/c9-7(10)15-3-1-13-6-4(16-8(11)12)2-14-5(3)6/h3-6H,1-2H2/t3-,4+,5-,6-/m1/s1
comment: Isosorbide dinitrate acts as a vasodilator. It is similar to nitroglycerin, but is slower to act.
iupac name: [(3S,3aS,6R,6aS)-6-nitrooxy-2,3,3a,5,6,6a-hexahydrofuro[2,3-d]furan-3-yl] nitrate
xref: CHEMBL6622
synonym: Sorbitrate
synonym: Dilatrate-Sr®
synonym: Isordil®
synonym: ISDN
approved: t
ligand name: isosorbide dinitrate
type: SyntheticOrganicLigand

perampanel
in ch i key: PRMWGUBFXWROHD-UHFFFAOYSA-N
in ch i: InChI=1S/C23H15N3O/c24-15-17-8-4-5-11-20(17)21-14-18(22-12-6-7-13-25-22)16-26(23(21)27)19-9-2-1-3-10-19/h1-14,16H
comment: Perampanel is an anticonvulsant. The drug is administered as perampanel hydrate. It is first and only FDA-approved non-competitive AMPA (alpha-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid) receptor antagonist.
iupac name: 2-(2-oxo-1-phenyl-5-pyridin-2-ylpyridin-3-yl)benzonitrile
xref: CHEMBL1214124
synonym: E2007
synonym: ER-155055-90
synonym: Fycompa®
approved: t
ligand name: perampanel
type: SyntheticOrganicLigand

teduglutide
in ch i key: CILIXQOJUNDIDU-ASQIGDHWSA-N
comment: Teduglutide is a glucagon-like peptide-2 (GLP-2) analogue in which position 2 amino acid alanine is replaced by glycine, increasing the peptide's resistance to proteolytic cleavage by dipeptidyl peptidase-4 (DPP-4) <Reference id=23850/>. The chemical structure shown here was generated using the SMILES from PubChem CID 16139605. The intestinotrophic effects of GLP-2 (e.g. promotion of intestinal growth, reduced epithelial cell apoptosis and inflammation) has led to the development of GLP-2 analogues like teduglutide for the treatment of GI disorders such as short bowel syndrome and inflammatory bowel diseases.
xref: CHEMBL2104987
synonym: GLP2-2G
synonym: ALX-0600
synonym: Gattex®
synonym: Revestive®
approved: t
ligand name: teduglutide
type: PeptideLigand

S-EMCA
in ch i key: NPBCMXATLRCCLF-IRRLEISYSA-N
in ch i: InChI=1S/C27H46O5/c1-6-17-20-12-16(28)9-10-26(20,4)21-13-22(29)27(5)18(14(2)11-15(3)25(31)32)7-8-19(27)23(21)24(17)30/h14-24,28-30H,6-13H2,1-5H3,(H,31,32)/t14-,15+,16-,17-,18-,19+,20+,21+,22+,23+,24-,26+,27-/m1/s1
comment: S-EMCA (INT-777) is a potent and selective agonist of the G-protein-coupled bile acid receptor TGR5 (gene symbol GPBAR1) which is formally known as the GPBA receptor <Reference id=23849/>. The GPBA receptor was historically identified as a metabolic regulator with roles in energy homeostasis, bile acid homeostasis, and glucose metabolism. More recently additional functions for the GPBA receptor such as regulation of the inflammatory response, cancer and liver regeneration have been described <Reference id=35280/>.
iupac name: (2S,4R)-4-[(3R,5S,6R,7R,8R,9S,10S,12S,13R,14S,17R)-6-ethyl-3,7,12-trihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-methylpentanoic acid
xref: CHEMBL567640
synonym: INT777
synonym: INT-777
synonym: 6α-ethyl-23(S)-methyl-cholic acid
approved: f
ligand name: S-EMCA
type: SyntheticOrganicLigand

zonisamide
canonical SMILES: NS(=O)(=O)Cc1noc2c1cccc2
isomeric SMILES: NS(=O)(=O)Cc1noc2c1cccc2
in ch i key: UBQNRHZMVUUOMG-UHFFFAOYSA-N
in ch i: InChI=1S/C8H8N2O3S/c9-14(11,12)5-7-6-3-1-2-4-8(6)13-10-7/h1-4H,5H2,(H2,9,11,12)
comment: Zonisamide is a sulfonamide anticonvulsant.
iupac name: 1,2-benzoxazol-3-ylmethanesulfonamide
xref: CHEMBL750
synonym: AD-810
synonym: CI-912
synonym: PD-110843
synonym: Zonegran®
approved: t
ligand name: zonisamide
type: SyntheticOrganicLigand

indisulam
in ch i key: SETFNECMODOHTO-UHFFFAOYSA-N
comment: Indisulam is an anticancer sulfonamide that is in clinical development. This compound belongs to the family of carbonic anhydrase inhibitors. It also behaves as a type of molecular glue that targets certain proteins for ubiquitination and proteasomal degradation <Reference id=42961/><Reference id=42962/>, by bringing them into the proximity the CUL4-DDB1-DDA1-DCAF15 E3 ubiquitin ligase complex.
iupac name: N-(3-chloro-1H-indol-7-yl)benzene-1,4-disulfonamide
xref: CHEMBL77517
synonym: E7070
approved: f
ligand name: indisulam
type: SyntheticOrganicLigand

dimethyl fumarate
canonical SMILES: COC(=O)C=CC(=O)OC
isomeric SMILES: COC(=O)/C=C/C(=O)OC
in ch i key: LDCRTTXIJACKKU-ONEGZZNKSA-N
in ch i: InChI=1S/C6H8O4/c1-9-5(7)3-4-6(8)10-2/h3-4H,1-2H3/b4-3+
comment: The active metabolite of dimethyl fumarate is <Ligand id=5786/>.
iupac name: dimethyl (E)-but-2-enedioate
xref: CHEMBL2107333
synonym: BG00012
synonym: fumaric acid
synonym: Fumaderm
synonym: BG-12
synonym: Tecfidera®
approved: t
ligand name: dimethyl fumarate
type: SyntheticOrganicLigand

AR244555
in ch i key: QKPSTNGNDWHYCH-UHFFFAOYSA-N
iupac name: (1'-but-3-enyl-5-chlorospiro[2H-indole-3,4'-piperidine]-1-yl)-(2,6-difluorophenyl)methanone
synonym: AR 244555
synonym: AR-244555
approved: f
ligand name: AR244555
type: SyntheticOrganicLigand

CGEN-856
in ch i key: SNXBDZJJBKGJKY-CBQXUBDJSA-N
synonym: P61
approved: f
ligand name: CGEN-856
type: PeptideLigand

CGEN-857
in ch i key: HPWUNEYLOMSFEY-HVUBXCGRSA-N
synonym: P33
approved: f
ligand name: CGEN-857
type: PeptideLigand

AR234960
in ch i key: TUSCHIFEASZBBF-UHFFFAOYSA-N
in ch i: InChI=1S/C27H30FN5O5S/c1-38-25-16-23(33(34)35)8-9-26(25)39(36,37)32-18-21(24(19-32)20-5-4-6-22(28)15-20)17-30-11-13-31(14-12-30)27-7-2-3-10-29-27/h2-10,15-16,21,24H,11-14,17-19H2,1H3
comment: Reference <Reference id=23755/> specifies that this compound is a racemate. We show the structure here without specified stereochemistry to represent the mixture. AR234960 is a mixture of two diastereomers, trans in relation to each other.
iupac name: 1-[[4-(3-fluorophenyl)-1-(2-methoxy-4-nitrophenyl)sulfonylpyrrolidin-3-yl]methyl]-4-pyridin-2-ylpiperazine
synonym: AR 234960
synonym: AR-234960
approved: f
ligand name: AR234960
type: SyntheticOrganicLigand

MBP7
in ch i key: NZCFITBCFLGDFN-JEDGRRCBSA-N
in ch i: InChI=1S/C41H78N16O11/c1-21(2)18-28(56-36(64)27(13-14-31(44)59)52-32(60)23(5)51-33(61)24(43)10-6-7-15-42)37(65)54-25(11-8-16-49-40(45)46)34(62)53-26(12-9-17-50-41(47)48)35(63)55-29(19-22(3)4)38(66)57-30(20-58)39(67)68/h21-30,58H,6-20,42-43H2,1-5H3,(H2,44,59)(H,51,61)(H,52,60)(H,53,62)(H,54,65)(H,55,63)(H,56,64)(H,57,66)(H,67,68)(H4,45,46,49)(H4,47,48,50)/t23-,24-,25-,26-,27-,28-,29-,30-/m0/s1
approved: f
ligand name: MBP7
type: PeptideLigand

apabetalone
in ch i key: NETXMUIMUZJUTB-UHFFFAOYSA-N
in ch i: InChI=1S/C20H22N2O5/c1-11-7-13(8-12(2)18(11)27-6-5-23)19-21-15-9-14(25-3)10-16(26-4)17(15)20(24)22-19/h7-10,23H,5-6H2,1-4H3,(H,21,22,24)
comment: Apabetalone (RVX 208) is a derivative of the plant polyphenol <Ligand id=8741/>. RVX 208 is an investigational inhibitor of BET bromodomain containing proteins, with potential anti-atherosclerotic action for the treatment of cardiovascular disease (CVD) <Reference id=29665/><Reference id=29666/>. SARS-CoV-2 and CIVID-19: Apabetalone (RVX 208) has been reported to reduce ACE2 expression and hence SARS-CoV-2 infection in vitro <Reference id=43610/>, and to block inflammation-mediated cardiac injury and dysfunction that is caused by SARS-CoV-2 infection (in a study using human cardiac organoids) <Reference id=43611/>. It has been respositioned for potential to provide a cardio-protective therapy that prevents COVID-19-mediated cardiac damage.
iupac name: 2-[4-(2-hydroxyethoxy)-3,5-dimethylphenyl]-5,7-dimethoxy-1,4-dihydroquinazolin-4-one
xref: CHEMBL2393130
synonym: RVX-208
synonym: QC-216
synonym: RVX-000222
synonym: RVX 208
approved: f
ligand name: apabetalone
type: SyntheticOrganicLigand

molibresib
in ch i key: AAAQFGUYHFJNHI-SFHVURJKSA-N
in ch i: InChI=1S/C22H22ClN5O2/c1-4-24-20(29)12-18-22-27-26-13(2)28(22)19-10-9-16(30-3)11-17(19)21(25-18)14-5-7-15(23)8-6-14/h5-11,18H,4,12H2,1-3H3,(H,24,29)/t18-/m0/s1
comment: I-BET compounds such as molibresib are acetyl histone mimetics. According to GSK's pipeline web resource they have terminated development of molibresib in cancer, as their emerging data did not support progression.
iupac name: 2-[(4S)-6-(4-chlorophenyl)-8-methoxy-1-methyl-4H-[1,2,4]triazolo[4,3-a][1,4]benzodiazepin-4-yl]-N-ethylacetamide
xref: CHEMBL1232461
synonym: I-BET-762
synonym: GSK-525762
synonym: I-BET762
synonym: GSK 525762A
synonym: CS-0717
synonym: GSK525762
approved: f
ligand name: molibresib
type: SyntheticOrganicLigand

compound 1 [PMID: 22795084]
canonical SMILES: O=C(Nc1ccc2c(c1)snn2)NCCC1=CCCCC1
isomeric SMILES: O=C(Nc1ccc2c(c1)snn2)NCCC1=CCCCC1
in ch i key: GGXCUZHEJUJACD-UHFFFAOYSA-N
in ch i: InChI=1S/C15H18N4OS/c20-15(16-9-8-11-4-2-1-3-5-11)17-12-6-7-13-14(10-12)21-19-18-13/h4,6-7,10H,1-3,5,8-9H2,(H2,16,17,20)
comment: This compound is an allosteric inhibitor of PRMT3 <Reference id=24179/>. The X-ray structure of compound 1 co-crystalised with PRMT shows binding at a novel site, distinct from the SAM (S-adenosyl methionime) and substrate peptide binding pockets <Reference id=24179/>. The Protein Databank (PDB) ID for this structure is 3SMQ, with the ligand called TDU rather than compound 1.
iupac name: 3-(1,2,3-benzothiadiazol-6-yl)-1-[2-(cyclohex-1-en-1-yl)ethyl]urea
xref: CHEMBL2325441
synonym: compound 1 (allosteric)
approved: f
ligand name: compound 1 [PMID: 22795084]
type: SyntheticOrganicLigand

compound 17f [PMID: 19632837]
in ch i key: PFOQIHIIOLBCEQ-UHFFFAOYSA-N
in ch i: InChI=1S/C24H32N4O2/c1-16-14-18(17-8-11-28(12-9-17)13-10-25-2)15-19-23(16)27-24(26-19)22-20(29-3)6-5-7-21(22)30-4/h5-7,14-15,17,25H,8-13H2,1-4H3,(H,26,27)
comment: This compound is a selcetive inhibitor of PRMT4 <Reference id=24178/>.
iupac name: (2-{4-[2-(2,6-dimethoxyphenyl)-4-methyl-1H-1,3-benzodiazol-6-yl]piperidin-1-yl}ethyl)(methyl)amine
xref: CHEMBL584335
synonym: benzo[d]imidazole inhibitors of PRMT4 from BMS
approved: f
ligand name: compound 17f [PMID: 19632837]
type: SyntheticOrganicLigand

BMS pyrazole inhibitor 7f
in ch i key: KODBDIFHMBDFOH-LBPRGKRZSA-N
iupac name: (2S)-2-amino-N-[(3-{5-[5-(1,3-benzothiazol-7-yl)-1,3,4-oxadiazol-2-yl]-3-(trifluoromethyl)-1H-pyrazol-1-yl}phenyl)methyl]propanamide
xref: CHEMBL468927
approved: f
ligand name: BMS pyrazole inhibitor 7f
type: SyntheticOrganicLigand

RM65
in ch i key: KBXOGBYQKMAAIA-UHFFFAOYSA-N
in ch i: InChI=1S/C34H32N2O4S2/c1-21(41-31-23-11-3-7-15-27(23)39-28-16-8-4-12-24(28)31)33(37)35-19-20-36-34(38)22(2)42-32-25-13-5-9-17-29(25)40-30-18-10-6-14-26(30)32/h3-18,21-22,31-32H,19-20H2,1-2H3,(H,35,37)(H,36,38)
xref: CHEMBL61824
approved: f
ligand name: RM65
type: SyntheticOrganicLigand

AMI-1
in ch i key: PCGISRHGYLRXSR-UHFFFAOYSA-N
in ch i: InChI=1S/C21H16N2O9S2/c24-19-9-15(33(27,28)29)7-11-5-13(1-3-17(11)19)22-21(26)23-14-2-4-18-12(6-14)8-16(10-20(18)25)34(30,31)32/h1-10,24-25H,(H2,22,23,26)(H,27,28,29)(H,30,31,32)
comment: We show the structure of J Acid urea as the parent molecule of AMI-1; AMI-1 is the sodium salt of this compound (see PubChem CID 16760626)
iupac name: 4-hydroxy-7-{[(5-hydroxy-7-sulfonaphthalen-2-yl)carbamoyl]amino}naphthalene-2-sulfonic acid
xref: CHEMBL221047
synonym: AMI1
synonym: AMI 1
approved: f
ligand name: AMI-1
type: SyntheticOrganicLigand

GSK-J1
in ch i key: AVZCPICCWKMZDT-UHFFFAOYSA-N
in ch i: InChI=1S/C22H23N5O2/c28-21(29)8-12-24-19-15-20(26-22(25-19)18-7-3-4-11-23-18)27-13-9-16-5-1-2-6-17(16)10-14-27/h1-7,11,15H,8-10,12-14H2,(H,28,29)(H,24,25,26)
comment: GSK-J1 is a catalytic site inhibitor that is somewhat selective for the H3K27me3-specific demethylases KDM6A and 6B (a.k.a. UTX and JMJD3 respectively) <Reference id=24169/>. The compund has also been shown to inhibit H3K4me3/me2 catalysed by KDM5 enzymes in vitro <Reference id=30418/>. This is a compound from the Structural Genomics Consortium's (SGC) Epigenetics Probes Collection. It reduces lipopolysaccharide-induced proinflammatory cytokine production by human primary macrophages, a process that depends on both JMJD3 and UTX.
iupac name: 3-{[2-(pyridin-2-yl)-6-(2,3,4,5-tetrahydro-1H-3-benzazepin-3-yl)pyrimidin-4-yl]amino}propanoic acid
xref: CHEMBL3188597
approved: f
ligand name: GSK-J1
type: SyntheticOrganicLigand

PBIT
canonical SMILES: Cc1ccc(cc1)n1sc2c(c1=O)cccc2
isomeric SMILES: Cc1ccc(cc1)n1sc2c(c1=O)cccc2
in ch i key: KRXMYBAZKJBJAB-UHFFFAOYSA-N
in ch i: InChI=1S/C14H11NOS/c1-10-6-8-11(9-7-10)15-14(16)12-4-2-3-5-13(12)17-15/h2-9H,1H3
comment: PBIT is a small molecule inhibitor of the histone demethylase subfamily KDM5 <Reference id=24166/>.
iupac name: 2-(4-methylphenyl)-1,2-benzothiazol-3-one
xref: CHEMBL1336959
approved: f
ligand name: PBIT
type: SyntheticOrganicLigand

daminozide
canonical SMILES: CN(NC(=O)CCC(=O)O)C
isomeric SMILES: CN(NC(=O)CCC(=O)O)C
in ch i key: NOQGZXFMHARMLW-UHFFFAOYSA-N
in ch i: InChI=1S/C6H12N2O3/c1-8(2)7-5(9)3-4-6(10)11/h3-4H2,1-2H3,(H,7,9)(H,10,11)
comment: Daminozide was used as a plant growth regulator but was withdrawn from use following public concern over risks to health posed by long term exposure, although the evidence of the level of risk is controversial. Investigations are now under way to assess the utility of daminozide as a histone demethylase inhibitor <Reference id=24165/>.
iupac name: 3-(N',N'-dimethylhydrazinecarbonyl)propanoic acid
xref: CHEMBL2164243
synonym: DMASA
synonym: SADH
synonym: B 995
synonym: Alar
synonym: Kylar
synonym: B-NINE
approved: f
ligand name: daminozide
type: SyntheticOrganicLigand

NCL-1
in ch i key: DTPSXFMGMQOVTG-ISJGIBHGSA-N
in ch i: InChI=1S/C27H29N3O3/c28-24-17-23(24)21-12-7-13-22(16-21)33-15-14-25(30-26(31)20-10-5-2-6-11-20)27(32)29-18-19-8-3-1-4-9-19/h1-13,16,23-25H,14-15,17-18,28H2,(H,29,32)(H,30,31)/t23-,24+,25+/m0/s1
comment: This is the 1S, 2R optical isomer of NCL-1. This isomer is more biologically active than the 1R, 2S isomer <Reference id=24162/>. Histone demethylation by KDM1A is suggested to be associated with some cancers and herpes simplex infection <Reference id=24163/><Reference id=24164/>. So, KDM1A inhibitors are of interest both as investigational tools and potential disease modifiers.
iupac name: (2R)-4-{3-[(1S,2R)-2-aminocyclopropyl]phenoxy}-N-benzyl-2-(phenylformamido)butanamide
approved: f
ligand name: NCL-1
type: SyntheticOrganicLigand

OG-L002
canonical SMILES: NC1CC1c1ccc(cc1)c1cccc(c1)O
isomeric SMILES: N[C@H]1C[C@@H]1c1ccc(cc1)c1cccc(c1)O
in ch i key: DSOJSZXQRJGBCW-CABCVRRESA-N
in ch i: InChI=1S/C15H15NO/c16-15-9-14(15)11-6-4-10(5-7-11)12-2-1-3-13(17)8-12/h1-8,14-15,17H,9,16H2/t14-,15+/m1/s1
comment: OG-L002 is a potent and selective inhibitor of the histone demethylase, lysine (K)-specific demethylase 1A (KDM1A aka LSD1).
iupac name: 3-{4-[(1R,2S)-2-aminocyclopropyl]phenyl}phenol
approved: f
ligand name: OG-L002
type: SyntheticOrganicLigand

nahuoic acid A
in ch i key: ZNAYXHSDZPSFLO-UWXUHECCSA-N
in ch i: InChI=1S/C30H50O7/c1-15(2)28(35)20(7)23(32)12-21(31)10-9-16(3)26-18(5)14-30(8)25(34)13-24(33)19(6)27(30)22(26)11-17(4)29(36)37/h9,11,14-15,19-28,31-35H,10,12-13H2,1-8H3,(H,36,37)/b16-9+,17-11+/t19-,20-,21-,22-,23+,24+,25+,26+,27+,28-,30+/m0/s1
comment: Isolated from a culture of a Streptomyces sp. obtained from a tropical marine sediment <Reference id=23743/>.
iupac name: (2E)-3-[(1R,2R,4aR,5R,7R,8R,8aS)-5,7-dihydroxy-3,4a,8-trimethyl-2-[(2E,5S,7R,8S,9S)-5,7,9-trihydroxy-8,10-dimethylundec-2-en-2-yl]-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]-2-methylprop-2-enoic acid
approved: f
ligand name: nahuoic acid A
type: SyntheticOrganicLigand

AZ505
in ch i key: LIBVHXXKHSODII-UHFFFAOYSA-N
iupac name: N-cyclohexyl-3-[2-(3,4-dichlorophenyl)ethylamino]-N-[2-[2-(5-hydroxy-3-oxo-4H-1,4-benzoxazin-8-yl)ethylamino]ethyl]propanamide
xref: CHEMBL2169920
synonym: AZ 505
synonym: AZ-505
approved: f
ligand name: AZ505
type: SyntheticOrganicLigand

SGC0946
in ch i key: IQCKJUKAQJINMK-HUBRGWSESA-N
in ch i: InChI=1S/C28H40BrN7O4/c1-16(2)35(12-6-11-31-27(39)34-18-9-7-17(8-10-18)28(3,4)5)14-20-22(37)23(38)26(40-20)36-13-19(29)21-24(30)32-15-33-25(21)36/h7-10,13,15-16,20,22-23,26,37-38H,6,11-12,14H2,1-5H3,(H2,30,32,33)(H2,31,34,39)/t20-,22-,23-,26-/m1/s1
comment: SGC0946 is a brominated analogue of <Ligand id=7377/> and is a DOT1L inhibitor <Reference id=24149/>. This is a compound from the Structural Genomics Consortium's (SGC) Epigenetics Probes Collection.
iupac name: 1-[3-[[(2R,3S,4R,5R)-5-(4-amino-5-bromopyrrolo[2,3-d]pyrimidin-7-yl)-3,4-dihydroxyoxolan-2-yl]methyl-propan-2-ylamino]propyl]-3-(4-tert-butylphenyl)urea
xref: CHEMBL3087498
approved: f
ligand name: SGC0946
type: SyntheticOrganicLigand

amidephrine
canonical SMILES: CNCC(c1cccc(c1)NS(=O)(=O)C)O
isomeric SMILES: CNCC(c1cccc(c1)NS(=O)(=O)C)O
in ch i key: ZHOWHMXTJFZXRB-UHFFFAOYSA-N
in ch i: InChI=1S/C10H16N2O3S/c1-11-7-10(13)8-4-3-5-9(6-8)12-16(2,14)15/h3-6,10-13H,7H2,1-2H3
xref: CHEMBL146408
approved: f
ligand name: amidephrine
type: SyntheticOrganicLigand

pinometostat
in ch i key: LXFOLMYKSYSZQS-LURJZOHASA-N
in ch i: InChI=1S/C30H42N8O3/c1-16(2)37(13-22-25(39)26(40)29(41-22)38-15-34-24-27(31)32-14-33-28(24)38)19-10-17(11-19)6-9-23-35-20-8-7-18(30(3,4)5)12-21(20)36-23/h7-8,12,14-17,19,22,25-26,29,39-40H,6,9-11,13H2,1-5H3,(H,35,36)(H2,31,32,33)/t17-,19+,22-,25-,26-,29-/m1/s1
comment: Pinometostat acts as a DOT1-like histone H3K79 methyltransferase (DOT1L) inhibitor that is being progressed through clinical evaluation in a collaboration between Cellgene and Epizyme, to evaluate its antileukemic efficacy in mixed-lineage leukemia (MLL)-rearranged leukemias. Link to Epizyme's pinometostat webpage here.
xref: CHEMBL3087499
synonym: EPZ 5676
synonym: EPZ-5676
synonym: EPZ5676
approved: f
ligand name: pinometostat
type: SyntheticOrganicLigand

bromo-deaza-SAH
in ch i key: DIULHULFPSIBAK-TWBCTODHSA-N
comment: Bromo-deaza-SAH is a small molecule inhibitor of the chromatin modifying enzymes DOT1-like histone H3K79 methyltransferase (DOT1L) and DNA (cytosine-5-)-methyltransferase 1 (DNMT1).
iupac name: (2S)-2-amino-4-[[(2S,3S,4R,5R)-5-(4-amino-5-bromopyrrolo[2,3-d]pyrimidin-7-yl)-3,4-dihydroxyoxolan-2-yl]methylsulfanyl]butanoic acid
xref: CHEMBL2349526
approved: f
ligand name: bromo-deaza-SAH
type: SyntheticOrganicLigand

ibuprofen
canonical SMILES: CC(Cc1ccc(cc1)C(C(=O)O)C)C
isomeric SMILES: CC(Cc1ccc(cc1)C(C(=O)O)C)C
in ch i key: HEFNNWSXXWATRW-UHFFFAOYSA-N
in ch i: InChI=1S/C13H18O2/c1-9(2)8-11-4-6-12(7-5-11)10(3)13(14)15/h4-7,9-10H,8H2,1-3H3,(H,14,15)
comment: Ibuprofen is a nonsteroidal anti-inflammatory drug (NSAID). The approved drug is a racemic mixture of the (R)- and (S)-stereoisomers. The (S)-enantiomer is more active, and the (R)-enantiomer is converted in the body to the (S)-enantiomer. We show the non-isomeric molecule to represent the mixture.
iupac name: 2-[4-(2-methylpropyl)phenyl]propanoic acid
xref: CHEMBL521
synonym: Act-3
synonym: Actiprofen
synonym: Adex
synonym: Adran
synonym: Advil Liqui-Gels
synonym: Aktren
synonym: Alaxan
synonym: Alges-X
synonym: Algoflex
synonym: Algofren
synonym: Alivium
synonym: Amersol
synonym: Amibufen
synonym: Anadin Ibuprofen
synonym: Anadin Joint Pain
synonym: Anco
synonym: Andran
synonym: Anflagen
synonym: Apo-Ibuprofen
synonym: Apsifen
synonym: Apsifen-F
synonym: Arthrofen
synonym: Artofen
synonym: Artril 300
synonym: Betagesic
synonym: Betaprofen
synonym: Bluton
synonym: Bonifen
synonym: Brufanic
synonym: Brufen Retard
synonym: Brufort
synonym: Buburone
synonym: Bugesic
synonym: Buprovil
synonym: Burana
synonym: Butylenin
synonym: Caldolor
synonym: Calprofen
synonym: Cap-Profen
synonym: Children's Advil
synonym: Children's Elixsure
synonym: Children's Ibuprofen
synonym: Children's Motrin
synonym: Codral
synonym: Dalsy
synonym: Dismenol
synonym: Diverin
synonym: Dolgirid
synonym: Dolgit
synonym: Dolo-Dolgit
synonym: Dolo-Spedifen
synonym: Dolocyl
synonym: Dolofort
synonym: Doloraz
synonym: Dolormin
synonym: Dorival
synonym: Ebufac
synonym: EmuProfen
synonym: Epobron
synonym: Espidifen
synonym: Eve
synonym: Femadon
synonym: Fenbid
synonym: Fenbid Spansule
synonym: Fenpaed
synonym: Finalflex
synonym: Galprofen
synonym: Haltran
synonym: Herron Blue
synonym: i-profen
synonym: Ibalgin
synonym: Ibrofen and Ibugan
synonym: Ibu

UNC0642
in ch i key: RNAMYOYQYRYFQY-UHFFFAOYSA-N
in ch i: InChI=1S/C29H44F2N6O2/c1-21(2)36-14-7-22(8-15-36)32-27-23-19-25(38-3)26(39-18-6-13-35-11-4-5-12-35)20-24(23)33-28(34-27)37-16-9-29(30,31)10-17-37/h19-22H,4-18H2,1-3H3,(H,32,33,34)
comment: UNCO0642 is compound 7 in <Reference id=24141/>. This is a compound from the Structural Genomics Consortium's (SGC) Epigenetics Probes Collection.
iupac name: 2-(4,4-difluoropiperidin-1-yl)-6-methoxy-N-(1-propan-2-ylpiperidin-4-yl)-7-(3-pyrrolidin-1-ylpropoxy)quinazolin-4-amine
xref: CHEMBL2441082
approved: f
ligand name: UNC0642
type: SyntheticOrganicLigand

BRD4770
in ch i key: UCGWYCMPZXDHNR-UHFFFAOYSA-N
in ch i: InChI=1S/C25H23N3O3/c1-31-24(30)20-14-15-22-21(17-20)26-25(27-23(29)19-12-6-3-7-13-19)28(22)16-8-11-18-9-4-2-5-10-18/h2-7,9-10,12-15,17H,8,11,16H2,1H3,(H,26,27,29)
comment: BRD4770 may be hydrolysed to BRD9539 (see <Reference id=24139/>) in cells, with the latter being the more active compound.
iupac name: methyl 2-benzamido-1-(3-phenylpropyl)benzimidazole-5-carboxylate
synonym: BRD-4770
synonym: BRD 4770
approved: f
ligand name: BRD4770
type: SyntheticOrganicLigand

UNC0638
in ch i key: QOECJCJVIMVJGX-UHFFFAOYSA-N
in ch i: InChI=1S/C30H47N5O2/c1-22(2)35-17-12-24(13-18-35)31-30-25-20-27(36-3)28(37-19-9-16-34-14-7-8-15-34)21-26(25)32-29(33-30)23-10-5-4-6-11-23/h20-24H,4-19H2,1-3H3,(H,31,32,33)
comment: This is a compound from the Structural Genomics Consortium's (SGC) Epigenetics Probes Collection.
iupac name: 2-cyclohexyl-6-methoxy-N-(1-propan-2-ylpiperidin-4-yl)-7-(3-pyrrolidin-1-ylpropoxy)quinazolin-4-amine
xref: CHEMBL1231795
approved: f
ligand name: UNC0638
type: SyntheticOrganicLigand

BIX-01294
in ch i key: OSXFATOLZGZLSK-UHFFFAOYSA-N
in ch i: InChI=1S/C28H38N6O2/c1-32-12-7-13-34(17-16-32)28-30-24-19-26(36-3)25(35-2)18-23(24)27(31-28)29-22-10-14-33(15-11-22)20-21-8-5-4-6-9-21/h4-6,8-9,18-19,22H,7,10-17,20H2,1-3H3,(H,29,30,31)
comment: BIX-01294 is a histone methyltransferase inhibitor <Reference id=24137/><Reference id=37841/>. BIX-01294-induced inhibition of H3K9me2 levels and upregulation of schizophrenia candidate gene expression suggests some therapeutic potential for histone modifying pharmacology in the treatment of schizophrenia <Reference id=37840/>.
iupac name: N-(1-benzylpiperidin-4-yl)-6,7-dimethoxy-2-(4-methyl-1,4-diazepan-1-yl)quinazolin-4-amine
xref: CHEMBL569864
synonym: BIX01294
synonym: BIX 01294
approved: f
ligand name: BIX-01294
type: SyntheticOrganicLigand

EI1
canonical SMILES: CCC(n1ccc2c1cc(C#N)cc2C(=O)NCc1c(C)cc([nH]c1=O)C)CC
isomeric SMILES: CCC(n1ccc2c1cc(C#N)cc2C(=O)NCc1c(C)cc([nH]c1=O)C)CC
in ch i key: PFHDWRIVDDIFRP-UHFFFAOYSA-N
in ch i: InChI=1S/C23H26N4O2/c1-5-17(6-2)27-8-7-18-19(10-16(12-24)11-21(18)27)22(28)25-13-20-14(3)9-15(4)26-23(20)29/h7-11,17H,5-6,13H2,1-4H3,(H,25,28)(H,26,29)
comment: EI1 is a potent and selective small molecule inhibitor of EZH2 (aka KMT6) <Reference id=23894/>.
iupac name: 6-cyano-N-[(4,6-dimethyl-2-oxo-1H-pyridin-3-yl)methyl]-1-pentan-3-ylindole-4-carboxamide
synonym: KB-145943
approved: f
ligand name: EI1
type: SyntheticOrganicLigand

GSK126
in ch i key: FKSFKBQGSFSOSM-QFIPXVFZSA-N
in ch i: InChI=1S/C31H38N6O2/c1-6-22(5)37-18-20(3)29-25(30(38)34-17-26-19(2)13-21(4)35-31(26)39)14-24(15-27(29)37)23-7-8-28(33-16-23)36-11-9-32-10-12-36/h7-8,13-16,18,22,32H,6,9-12,17H2,1-5H3,(H,34,38)(H,35,39)/t22-/m0/s1
comment: GSK126 is a potent and selective small-molecule inhibitor of EZH2 (KMT6) methyltransferase activity <Reference id=23892/>. This is likely to be the ligand with the extended reseaerch code GSK2816126, which has anti-lymphoma potential.
iupac name: 1-[(2S)-butan-2-yl]-N-[(4,6-dimethyl-2-oxo-1H-pyridin-3-yl)methyl]-3-methyl-6-(6-piperazin-1-ylpyridin-3-yl)indole-4-carboxamide
xref: CHEMBL3287735
synonym: GSK 126
synonym: GSK-126
synonym: GSK2816126
approved: f
ligand name: GSK126
type: SyntheticOrganicLigand

tazemetostat
in ch i key: NSQSAUGJQHDYNO-UHFFFAOYSA-N
in ch i: InChI=1S/C34H44N4O4/c1-5-38(29-10-14-41-15-11-29)32-20-28(27-8-6-26(7-9-27)22-37-12-16-42-17-13-37)19-30(25(32)4)33(39)35-21-31-23(2)18-24(3)36-34(31)40/h6-9,18-20,29H,5,10-17,21-22H2,1-4H3,(H,35,39)(H,36,40)
comment: Tazemetostat is an oral, potent, first-in-class inhibitor of the histone methyltransferase, enhancer of zeste 2 polycomb repressive complex 2 subunit (EZH2) that was developed by Epizyme as anovel drug for the treatment of solid tumours and lymphomas with speciific genetic alterations. Link to Epizyme's tazemetostat webpage here.
iupac name: N-[(4,6-dimethyl-2-oxo-1H-pyridin-3-yl)methyl]-3-[ethyl(oxan-4-yl)amino]-2-methyl-5-[4-(morpholin-4-ylmethyl)phenyl]benzamide
synonym: Tazverik®
synonym: EPZ 6438
synonym: EPZ-6438
synonym: EPZ6438
synonym: E-7438
approved: t
ligand name: tazemetostat
type: SyntheticOrganicLigand

ricolinostat
in ch i key: QGZYDVAGYRLSKP-UHFFFAOYSA-N
in ch i: InChI=1S/C24H27N5O3/c30-22(28-32)15-9-1-2-10-16-25-23(31)19-17-26-24(27-18-19)29(20-11-5-3-6-12-20)21-13-7-4-8-14-21/h3-8,11-14,17-18,32H,1-2,9-10,15-16H2,(H,25,31)(H,28,30)
comment: Rocilinostat is an investigational HDAC6 inhibitor <Reference id=24127/>. But note that it exhibits only ~10-fold enzymic selectivity against the class I isoform, HDAC1.
iupac name: N-[7-(hydroxyamino)-7-oxoheptyl]-2-(N-phenylanilino)pyrimidine-5-carboxamide
xref: CHEMBL2364628
synonym: ACY-1215
approved: f
ligand name: ricolinostat
type: SyntheticOrganicLigand

valproic acid
canonical SMILES: CCCC(C(=O)O)CCC
isomeric SMILES: CCCC(C(=O)O)CCC
in ch i key: NIJJYAXOARWZEE-UHFFFAOYSA-N
in ch i: InChI=1S/C8H16O2/c1-3-5-7(6-4-2)8(9)10/h7H,3-6H2,1-2H3,(H,9,10)
comment: Valproic acid is a fatty acid with anticonvulsant properties. It is commonly administered in a salt preparation, valproate sodium.
iupac name: 2-propylpentanoic acid
xref: CHEMBL109
synonym: A-44090
synonym: Depacon
synonym: Stavzor
synonym: Depakene
synonym: Divalproex Sodium
synonym: Depakote®
synonym: valproate sodium
synonym: Epilim®
approved: t
ligand name: valproic acid
type: SyntheticOrganicLigand

mocetinostat
in ch i key: HRNLUBSXIHFDHP-UHFFFAOYSA-N
in ch i: InChI=1S/C23H20N6O/c24-19-5-1-2-6-21(19)28-22(30)17-9-7-16(8-10-17)14-27-23-26-13-11-20(29-23)18-4-3-12-25-15-18/h1-13,15H,14,24H2,(H,28,30)(H,26,27,29)
comment: Mocetinostat inhibits Class I HDACs <Reference id=23750/>.
iupac name: N-(2-aminophenyl)-4-({[4-(pyridin-3-yl)pyrimidin-2-yl]amino}methyl)benzamide
xref: CHEMBL272980
synonym: MGCD0103
approved: f
ligand name: mocetinostat
type: SyntheticOrganicLigand

entinostat
in ch i key: INVTYAOGFAGBOE-UHFFFAOYSA-N
in ch i: InChI=1S/C21H20N4O3/c22-18-5-1-2-6-19(18)25-20(26)17-9-7-15(8-10-17)13-24-21(27)28-14-16-4-3-11-23-12-16/h1-12H,13-14,22H2,(H,24,27)(H,25,26)
comment: Entinostat (MS-275) inhibits Class I histone deacetylases (HDACs 1, 2, 3 & 8), but has been shown to be somewhat selective for HDAC1 <Reference id=23898/><Reference id=23750/>. Studies in rodent models of inflammation suggest that inhibition by entinostat may be clinically useful <Reference id=23899/><Reference id=23900/><Reference id=23901/><Reference id=23902/>, perhaps more so than broader acting Class I HDAC inhibitors such as vorinostat (SAHA) <Reference id=23902/>.
iupac name: pyridin-3-ylmethyl N-({4-[(2-aminophenyl)carbamoyl]phenyl}methyl)carbamate
xref: CHEMBL27759
synonym: BAY 86-5274
synonym: ZK 244894
synonym: MS-275
synonym: SNDX-275
approved: f
ligand name: entinostat
type: SyntheticOrganicLigand

compound 12 [PMID: 19800804]
in ch i key: QSPCKQSNISDWOH-UHFFFAOYSA-N
in ch i: InChI=1S/C16H11NO5/c1-9-2-4-10(5-3-9)22-11-6-7-12-13(8-11)15(19)17(14(12)18)16(20)21/h2-8H,1H3,(H,20,21)
iupac name: 5-(4-methylphenoxy)-1,3-dioxoisoindole-2-carboxylic acid
approved: f
ligand name: compound 12 [PMID: 19800804]
type: SyntheticOrganicLigand

romidepsin
in ch i key: OHRURASPPZQGQM-GCCNXGTGSA-N
in ch i: InChI=1S/C24H36N4O6S2/c1-6-16-21(30)28-20(14(4)5)24(33)34-15-9-7-8-10-35-36-12-17(22(31)25-16)26-23(32)19(13(2)3)27-18(29)11-15/h6-7,9,13-15,17,19-20H,8,10-12H2,1-5H3,(H,25,31)(H,26,32)(H,27,29)(H,28,30)/b9-7+,16-6-/t15-,17-,19-,20+/m1/s1
comment: Romidepsin is an anticancer agent originally isolated from the bacterium Chromobacterium violaceum, but subsequently produced synthetically. Romidepsin is an inhibitor of Class II histone deacetylases (HDACs).
iupac name: (1S,4S,7Z,10S,16E,21R)-7-ethylidene-4,21-bis(propan-2-yl)-2-oxa-12,13-dithia-5,8,20,23-tetraazabicyclo[8.7.6]tricos-16-ene-3,6,9,19,22-pentone
xref: CHEMBL343448
synonym: FK228
synonym: FR901228
synonym: Istodax®
approved: t
ligand name: romidepsin
type: SyntheticOrganicLigand

trichostatin A
isomeric SMILES: ONC(=O)/C=C/C(=C/[C@H](C(=O)c1ccc(cc1)N(C)C)C)/C
in ch i key: RTKIYFITIVXBLE-QEQCGCAPSA-N
in ch i: InChI=1S/C17H22N2O3/c1-12(5-10-16(20)18-22)11-13(2)17(21)14-6-8-15(9-7-14)19(3)4/h5-11,13,22H,1-4H3,(H,18,20)/b10-5+,12-11+/t13-/m1/s1
comment: Trichostatin A Inhibits Class I and II histone deacetylases (HDACs), but NOT the Class III HDACs (sirtuins (SIRTs) 1-7), so is therefore a useful probe of histone deacetylase activity. HDAC1 has been tagged as the drug's primary target for data retrieval purposes only and in no way infers that this is the only target of this drug.
iupac name: (2E,4E,6R)-7-[4-(dimethylamino)phenyl]-N-hydroxy-4,6-dimethyl-7-oxohepta-2,4-dienamide
xref: CHEMBL99
approved: f
ligand name: trichostatin A
type: SyntheticOrganicLigand

C646
canonical SMILES: CC1=NN(C(=O)C1=Cc1ccc(o1)c1cc(C)c(cc1[N+](=O)[O-])C)c1ccc(cc1)C(=O)O
isomeric SMILES: CC1=NN(C(=O)/C/1=C/c1ccc(o1)c1cc(C)c(cc1[N+](=O)[O-])C)c1ccc(cc1)C(=O)O
in ch i key: HEKJYZZSCQBJGB-UNOMPAQXSA-N
in ch i: InChI=1S/C24H19N3O6/c1-13-10-20(21(27(31)32)11-14(13)2)22-9-8-18(33-22)12-19-15(3)25-26(23(19)28)17-6-4-16(5-7-17)24(29)30/h4-12H,1-3H3,(H,29,30)/b19-12-
comment: The structure represented here was drawn from <Reference id=24136/>, with our structure showing the charges on the nitro functional group. However, this molecule is drawn with one unspecified bond in <Reference id=24573/> which matches PubChem CID 2871948. A 2017 article by Dahlin et al. suggests that the thiol-reactivity of C464 brings in to question its activity as a selective HAT inhibitor <Reference id=33784/>, and this is somewhat confirmed by evidence of histone deacetylase inhibition reported in <Reference id=34144/>.
iupac name: 4-[(4Z)-4-{[5-(4,5-dimethyl-2-nitrophenyl)furan-2-yl]methylidene}-3-methyl-5-oxo-4,5-dihydro-1H-pyrazol-1-yl]benzoic acid
xref: CHEMBL1797936
approved: f
ligand name: C646
type: SyntheticOrganicLigand

plumbagin
canonical SMILES: CC1=CC(=O)c2c(C1=O)cccc2O
isomeric SMILES: CC1=CC(=O)c2c(C1=O)cccc2O
in ch i key: VCMMXZQDRFWYSE-UHFFFAOYSA-N
in ch i: InChI=1S/C11H8O3/c1-6-5-9(13)10-7(11(6)14)3-2-4-8(10)12/h2-5,12H,1H3
comment: Plumbagin is a genotoxic and mutagenic plant-derived toxin. It has some activity as a histone acetyltransferase (HAT) inhibitor, however a 2017 article by Dahlin et al. suggests that the thiol-reactivity of plumbagin brings in to question its HAT inhibitor activity <Reference id=33784/>.
iupac name: 5-hydroxy-2-methyl-1,4-dihydronaphthalene-1,4-dione
xref: CHEMBL295316
synonym: RTK1
approved: f
ligand name: plumbagin
type: NaturalProductLigand

cyanotriphenylborate
canonical SMILES: N#C[B-](c1ccccc1)(c1ccccc1)c1ccccc1
isomeric SMILES: N#C[B-](c1ccccc1)(c1ccccc1)c1ccccc1
in ch i key: HYJITQQQMJSBOL-UHFFFAOYSA-N
in ch i: InChI=1S/C19H15BN/c21-16-20(17-10-4-1-5-11-17,18-12-6-2-7-13-18)19-14-8-3-9-15-19/h1-15H/q-1
comment: This compound is also used in complex with sodium (CID 23665403).
iupac name: cyano-tri(phenyl)boron
xref: CHEMBL1628709
approved: f
ligand name: cyanotriphenylborate
type: SyntheticOrganicLigand

epigallocatechin-3-gallate
in ch i key: WMBWREPUVVBILR-WIYYLYMNSA-N
in ch i: InChI=1S/C22H18O11/c23-10-5-12(24)11-7-18(33-22(31)9-3-15(27)20(30)16(28)4-9)21(32-17(11)6-10)8-1-13(25)19(29)14(26)2-8/h1-6,18,21,23-30H,7H2/t18-,21-/m1/s1
comment: Epigallocatechin-3-gallate (EGCG) is one of the catechins that are found in green tea. It had been ascribed activity as a histone acetyltransferase (HAT) inhibitor. However, a 2017 article by Dahlin et al. suggests that the thiol-reactivity of EGCG brings in to question its activity as a HAT inhibitor <Reference id=33784/>. Amongst the plethora of health benefits attributed to the catechins, EGCG has demonstrated broad-spectrum antiviral activity <Reference id=43676/><Reference id=43677/><Reference id=43678/><Reference id=43679/><Reference id=43680/>. SARS-CoV-2 and COVID-19: In relation to SARS-CoV-2, molecular docking analysis suggests that EGCG interacts with the virus' S protein and main protease (Mpro; 3CLpro) <Reference id=43681/>. Evidence also suggests that catechins bind to the S1 ubiquitin-binding site of the virus' second protease PLPro. It is hypothesised that inhibiting PLPro will reduce the enzyme's inhibitory function on the host ubiquitin proteasome and interferon stimulated gene systems, thus targeting some of the inflammatory aspects of SARS-CoV-2 infection.
iupac name: (2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate
xref: CHEMBL297453
synonym: EGCG
synonym: epigallocatechin gallate
approved: f
ligand name: epigallocatechin-3-gallate
type: NaturalProductLigand

garcinol
in ch i key: DTTONLKLWRTCAB-SMDXAGPFSA-N
in ch i: InChI=1S/C38H50O6/c1-22(2)11-13-27(25(7)8)20-37-21-28(15-12-23(3)4)36(9,10)38(35(37)44,18-17-24(5)6)34(43)31(33(37)42)32(41)26-14-16-29(39)30(40)19-26/h11-12,14,16-17,19,27-28,39-41H,7,13,15,18,20-21H2,1-6,8-10H3/t27-,28+,37+,38-/m0/s1
comment: The is some ambiguity as to the exact stereochemistry of garcinol, with several representations of the structure listed on PubChem. It has been ascribed activity as a histone acetyltransferase (HAT) inhibitor. However, a 2017 article by Dahlin et al. suggests that the garcinol non-specifically perturbs biological assays, bringing in to question its HAT inhibitor activity <Reference id=33784/>.
iupac name: (1S,5R,7R)-3-[(3,4-dihydroxyphenyl)(hydroxy)methylidene]-6,6-dimethyl-1-[(2S)-5-methyl-2-(prop-1-en-2-yl)hex-4-en-1-yl]-5,7-bis(3-methylbut-2-en-1-yl)bicyclo[3.3.1]nonane-2,4,9-trione
approved: f
ligand name: garcinol
type: NaturalProductLigand

curcumin
isomeric SMILES: COc1cc(/C=C/C(=O)CC(=O)/C=C/c2ccc(c(c2)OC)O)ccc1O
in ch i key: VFLDPWHFBUODDF-FCXRPNKRSA-N
in ch i: InChI=1S/C21H20O6/c1-26-20-11-14(5-9-18(20)24)3-7-16(22)13-17(23)8-4-15-6-10-19(25)21(12-15)27-2/h3-12,24-25H,13H2,1-2H3/b7-3+,8-4+
comment: Curcumin's physicochemical properties imply that it is an implausible clinical lead <Reference id=43502/>. It is unstable, reactive, and nonbioavailable, and has been identified as having attributes of both PAINS (pan-assay interference compounds) and IMPS (invalid metabolic panaceas) compounds.
iupac name: (1E,6E)-1,7-bis(4-hydroxy-3-methoxyphenyl)hepta-1,6-diene-3,5-dione
xref: CHEMBL140
approved: f
ligand name: curcumin
type: NaturalProductLigand

anacardic acid
canonical SMILES: C=CCC=CCC=CCCCCCCCc1cccc(c1C(=O)O)O
isomeric SMILES: C=CC/C=C/C/C=C/CCCCCCCc1cccc(c1C(=O)O)O
in ch i key: QUVGEKPNSCFQIR-AOSYACOCSA-N
in ch i: InChI=1S/C22H30O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-16-19-17-15-18-20(23)21(19)22(24)25/h2,4-5,7-8,15,17-18,23H,1,3,6,9-14,16H2,(H,24,25)/b5-4+,8-7+
comment: Anacardic acid has been ascribed activity as a histone acetyltransferase (HAT) inhibitor. However, a 2017 article by Dahlin et al. suggests that anacardic acid non-specifically perturbs biological assays, bringing in to question its HAT inhibitor activity <Reference id=33784/>.
iupac name: 2-hydroxy-6-[(8E,11E)-pentadeca-8,11,14-trien-1-yl]benzoic acid
xref: CHEMBL464925
approved: f
ligand name: anacardic acid
type: NaturalProductLigand

NIBR-0213
in ch i key: KYHUARFFBDLROH-MOPGFXCFSA-N
in ch i: InChI=1S/C27H29ClN2O3/c1-15-11-20(9-10-24(15)28)18(4)29-23-8-6-7-21(14-23)22-12-16(2)25(17(3)13-22)26(31)30-19(5)27(32)33/h6-14,18-19,29H,1-5H3,(H,30,31)(H,32,33)/t18-,19+/m1/s1
iupac name: (2S)-2-[[4-[3-[[(1R)-1-(4-chloro-3-methylphenyl)ethyl]amino]phenyl]-2,6-dimethylbenzoyl]amino]propanoic acid
xref: CHEMBL3086703
approved: f
ligand name: NIBR-0213
type: SyntheticOrganicLigand

(S)-FTY720-phosphate
canonical SMILES: CCCCCCCCc1ccc(cc1)CCC(COP(=O)(O)O)(CO)N
in ch i key: LRFKWQGGENFBFO-IBGZPJMESA-N
in ch i: InChI=1S/C19H34NO5P/c1-2-3-4-5-6-7-8-17-9-11-18(12-10-17)13-14-19(20,15-21)16-25-26(22,23)24/h9-12,21H,2-8,13-16,20H2,1H3,(H2,22,23,24)/t19-/m0/s1
iupac name: [(2S)-2-amino-2-(hydroxymethyl)-4-(4-octylphenyl)butyl] dihydrogen phosphate
xref: CHEMBL366208
approved: f
ligand name: (S)-FTY720-phosphate
type: SyntheticOrganicLigand

octyl thiophosphatidic acid
canonical SMILES: CCCCCCCCOCC(COP(=S)(O)O)OCCCCCCCC
isomeric SMILES: CCCCCCCCOC[C@@H](COP(=S)(O)O)OCCCCCCCC
in ch i key: PLCCQSPJUXGEHV-IBGZPJMESA-N
in ch i: InChI=1S/C19H41O5PS/c1-3-5-7-9-11-13-15-22-17-19(18-24-25(20,21)26)23-16-14-12-10-8-6-4-2/h19H,3-18H2,1-2H3,(H2,20,21,26)/t19-/m0/s1
iupac name: [(2S)-2,3-dioctoxypropoxy]-dihydroxy-sulfanylidene-$l^{5}-phosphane
xref: CHEMBL427017
approved: f
ligand name: octyl thiophosphatidic acid
type: SyntheticOrganicLigand

alkyl glycerol phosphate 18:1
canonical SMILES: CCCCCCCCCCCCCCCCCCOCC(COP(=O)(O)O)O
in ch i key: HUUYDUFSUADEJQ-NRFANRHFSA-N
iupac name: [(2S)-2-hydroxy-3-octadecoxypropyl] dihydrogen phosphate
synonym: AGP 18.1
approved: f
ligand name: alkyl glycerol phosphate 18:1
type: SyntheticOrganicLigand

compound 15 [PMID: 18178086]
in ch i key: WBVRCGUUZYPAGR-INIZCTEOSA-N
iupac name: N-[(2S)-1-[4-[(3,4-dichlorophenyl)-dimethylidene-$l^{6}-sulfanyl]piperazin-1-yl]propan-2-yl]-7-methylthieno[3,2-d]pyrimidin-4-amine
approved: f
ligand name: compound 15 [PMID: 18178086]
type: SyntheticOrganicLigand

VPC03090-P
in ch i key: LNMFICMTNRORPU-UHFFFAOYSA-N
in ch i: InChI=1S/C19H32NO4P/c1-2-3-4-5-6-7-9-16-10-8-11-17(12-16)18-13-19(20,14-18)15-24-25(21,22)23/h8,10-12,18H,2-7,9,13-15,20H2,1H3,(H2,21,22,23)
iupac name: [1-amino-3-(3-octylphenyl)cyclobutyl]methyl dihydrogen phosphate
synonym: VPC-03090-P
synonym: VPC 03090-P
approved: f
ligand name: VPC03090-P
type: SyntheticOrganicLigand

[1-bromo-(3S)-hydrox-4-(palmitoyloxy)butyl]phosphate
in ch i key: XCUPLWPVEJCIBO-HMEPSURWSA-M
in ch i: InChI=1S/C20H40BrO6P.Na/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-20(23)27-17-18(22)16-19(21)28(24,25)26;/h18-19,22H,2-17H2,1H3,(H2,24,25,26);/q;+1/p-1/t18-,19?;/m0./s1
iupac name: sodium;[(3S)-1-bromo-4-hexadecanoyloxy-3-hydroxybutyl]-hydroxyphosphinate
approved: f
ligand name: [1-bromo-(3S)-hydrox-4-(palmitoyloxy)butyl]phosphate
type: SyntheticOrganicLigand

AM095
in ch i key: LNDDRUPAICPXIN-GOSISDBHSA-N
in ch i: InChI=1S/C27H24N2O5/c1-17-25(28-27(32)33-18(2)20-6-4-3-5-7-20)26(34-29-17)23-14-12-22(13-15-23)21-10-8-19(9-11-21)16-24(30)31/h3-15,18H,16H2,1-2H3,(H,28,32)(H,30,31)/t18-/m1/s1
iupac name: 2-[4-[4-[3-methyl-4-[[(1R)-1-phenylethoxy]carbonylamino]-1,2-oxazol-5-yl]phenyl]phenyl]acetic acid
xref: CHEMBL2182052
synonym: AM 095
synonym: AM-095
approved: f
ligand name: AM095
type: SyntheticOrganicLigand

anti-BrP-LPA
in ch i key: HLVKVWDSLLFMSX-RBUKOAKNSA-N
in ch i: InChI=1S/C20H40BrO6P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-20(23)27-17-18(22)16-19(21)28(24,25)26/h18-19,22H,2-17H2,1H3,(H2,24,25,26)/t18-,19+/m0/s1
iupac name: [(1S,3S)-1-bromo-4-hexadecanoyloxy-3-hydroxybutyl]phosphonic acid
approved: f
ligand name: anti-BrP-LPA
type: SyntheticOrganicLigand

syn-BrP-LPA
in ch i key: HLVKVWDSLLFMSX-OALUTQOASA-N
in ch i: InChI=1S/C20H40BrO6P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-20(23)27-17-18(22)16-19(21)28(24,25)26/h18-19,22H,2-17H2,1H3,(H2,24,25,26)/t18-,19-/m0/s1
iupac name: [(1R,3S)-1-bromo-4-hexadecanoyloxy-3-hydroxybutyl]phosphonic acid
approved: f
ligand name: syn-BrP-LPA
type: SyntheticOrganicLigand

tetraethylammonium
canonical SMILES: CC[N+](CC)(CC)CC
isomeric SMILES: CC[N+](CC)(CC)CC
in ch i key: CBXCPBUEXACCNR-UHFFFAOYSA-N
in ch i: InChI=1S/C8H20N/c1-5-9(6-2,7-3)8-4/h5-8H2,1-4H3/q+1
iupac name: tetraethylazanium
xref: CHEMBL9324
approved: f
ligand name: tetraethylammonium
type: SyntheticOrganicLigand

T13
in ch i key: DFEVXZSENXLXQQ-LYOQJJATSA-M
in ch i: InChI=1S/C23H43O6PS.Na/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-23(24)28-22-20-27-19-18-21(22)29-30(25,26)31;/h9-10,21-22H,2-8,11-20H2,1H3,(H2,25,26,31);/q;+1/p-1/b10-9-;/t21-,22+;/m0./s1
iupac name: sodium;[(3R,4S)-3-[(Z)-octadec-9-enoyl]oxyoxan-4-yl]oxy-sulfidophosphinic acid
approved: f
ligand name: T13
type: SyntheticOrganicLigand

oleoyl-thiophosphate
isomeric SMILES: CCCCCCCC/C=C/CCCCCCCC(=O)OP(=O)(SC(=O)CCCCCCC/C=C/CCCCCCCC)OC(=O)CCCCCCC/C=C/CCCCCCCC
in ch i key: VZTWVTAPKVGVJL-IUPFWZBJSA-N
iupac name: [[(Z)-octadec-9-enoyl]oxy-[(Z)-octadec-9-enoyl]sulfanylphosphoryl] (Z)-octadec-9-enoate
approved: f
ligand name: oleoyl-thiophosphate
type: SyntheticOrganicLigand

NAEPA
canonical SMILES: CCCCCCCCC=CCCCCCCCC(=O)NCCOP(=O)(O)O
isomeric SMILES: CCCCCCCC/C=C/CCCCCCCC(=O)NCCOP(=O)(O)O
in ch i key: BCSUWOZFWWBYSX-MDZDMXLPSA-N
in ch i: InChI=1S/C20H40NO5P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-20(22)21-18-19-26-27(23,24)25/h9-10H,2-8,11-19H2,1H3,(H,21,22)(H2,23,24,25)/b10-9+
iupac name: 2-[[(E)-octadec-9-enoyl]amino]ethyl dihydrogen phosphate
xref: CHEMBL1574292
synonym: N-acyl ethanolamide phosphate
approved: f
ligand name: NAEPA
type: SyntheticOrganicLigand

amlodipine
in ch i key: HTIQEAQVCYTUBX-UHFFFAOYSA-N
in ch i: InChI=1S/C20H25ClN2O5/c1-4-28-20(25)18-15(11-27-10-9-22)23-12(2)16(19(24)26-3)17(18)13-7-5-6-8-14(13)21/h5-8,17,23H,4,9-11,22H2,1-3H3
comment: Amlodipine is a long-acting dihydropyridine class calcium channel blocker. Amlodipine is on the World Health Organisation's List of Essential Medicines. Click here to access the pdf version of the WHO's 21st Essential Medicines list (2019).
iupac name: O3-ethyl O5-methyl 2-(2-aminoethoxymethyl)-4-(2-chlorophenyl)-6-methyl-1,4-dihydropyridine-3,5-dicarboxylate
xref: CHEMBL1491
synonym: Copalia® (amlodipine + valsartan)
synonym: Katerzia&reg (amlodipine oral suspension, 1 mg/mL)
synonym: Norvasc®
synonym: UK-4834011
synonym: Amvaz
synonym: amlodipine maleate
synonym: amlodipine besylate
approved: t
ligand name: amlodipine
type: SyntheticOrganicLigand

azidopine
in ch i key: SWMHKFTXBOJETC-UHFFFAOYSA-N
in ch i: InChI=1S/C27H26F3N5O5/c1-4-39-25(37)21-15(2)33-16(3)22(23(21)19-7-5-6-8-20(19)27(28,29)30)26(38)40-14-13-32-24(36)17-9-11-18(12-10-17)34-35-31/h5-12,23,33H,4,13-14H2,1-3H3,(H,32,36)
iupac name: O3-[2-[(4-azidobenzoyl)amino]ethyl] O5-ethyl 2,6-dimethyl-4-[2-(trifluoromethyl)phenyl]-1,4-dihydropyridine-3,5-dicarboxylate
xref: CHEMBL1993397
approved: f
ligand name: azidopine
type: SyntheticOrganicLigand

semagacestat
in ch i key: PKXWXXPNHIWQHW-RCBQFDQVSA-N
in ch i: InChI=1S/C19H27N3O4/c1-11(2)16(23)18(25)20-12(3)17(24)21-15-14-8-6-5-7-13(14)9-10-22(4)19(15)26/h5-8,11-12,15-16,23H,9-10H2,1-4H3,(H,20,25)(H,21,24)/t12-,15-,16-/m0/s1
comment: Semagacestat is a small-molecule γ-secretase inhibitor that was developed by Eli Lilly as a potential treatment for Alzheimer's disease but it failed in Phase 3 clinical trials. NOTCH is also a γ-secretase substrate <Reference id=38116/>, and on-target inhibition of NOTCH receptor-related signalling by semagacestat treatment is proposed to be (at least in part) responsible for the unacceptable side effects that were noted in clinical trials, and which lead to termination of the trials <Reference id=23542/>.
iupac name: (2S)-2-hydroxy-3-methyl-N-[(2S)-1-[[(1S)-3-methyl-2-oxo-4,5-dihydro-1H-3-benzazepin-1-yl]amino]-1-oxopropan-2-yl]butanamide
xref: CHEMBL520733
synonym: LY-450139
approved: f
ligand name: semagacestat
type: SyntheticOrganicLigand

compound 19a [PMID: 24359159]
in ch i key: QHXBWJSQXSYAGG-VIFPVBQESA-N
in ch i: InChI=1S/C16H16FN9/c1-9(13-19-5-10(17)6-20-13)22-16-24-14-11(3-4-18-14)15(25-16)23-12-7-26(2)8-21-12/h3-9H,1-2H3,(H3,18,22,23,24,25)/t9-/m0/s1
comment: Compound 19a is a potent, orally bioavailable Jak2 inhibitor <Reference id=23539/>, although data from this article suggest that 19a is equipotent (IC50 <3nM) at JAK1 and JAK2, but with significantly lower affinity for JAK3 (IC50 220nM).
iupac name: 2-N-[(1S)-1-(5-fluoropyrimidin-2-yl)ethyl]-4-N-(1-methylimidazol-4-yl)- 7H-pyrrolo[2,3-d]pyrimidine-2,4-diamine
xref: CHEMBL3116050
approved: f
ligand name: compound 19a [PMID: 24359159]
type: SyntheticOrganicLigand

chlorpheniramine
canonical SMILES: CN(CCC(c1ccccn1)c1ccc(cc1)Cl)C
isomeric SMILES: CN(CCC(c1ccccn1)c1ccc(cc1)Cl)C
in ch i key: SOYKEARSMXGVTM-UHFFFAOYSA-N
in ch i: InChI=1S/C16H19ClN2/c1-19(2)12-10-15(16-5-3-4-11-18-16)13-6-8-14(17)9-7-13/h3-9,11,15H,10,12H2,1-2H3
comment: The approved drug is a racemic mixture of stereoisomers; <Ligand id=1213/> (R-isomer) and <Ligand id=1210/> (S-isomer). We show the non-isomeric molecule to represent the mixture.
iupac name: 3-(4-chlorophenyl)-N,N-dimethyl-3-pyridin-2-ylpropan-1-amine
xref: CHEMBL505
synonym: Antagonate
synonym: Kloromin
synonym: Isoclor
synonym: Chlor-Trimeton
synonym: Teldrin®
synonym: Phenetron®
synonym: chlorprophenpyridamine maleate
approved: t
ligand name: chlorpheniramine
type: SyntheticOrganicLigand

vismodegib
in ch i key: BPQMGSKTAYIVFO-UHFFFAOYSA-N
comment: Vismodegib inhibits smoothened homolog (SMO), a constituent of the Hedgehog signalling pathway which is essential for proper embryonic development. This pathway is also involved in the maintenance and regeneration of adult tissues by regulating adult stem cells and has been implicated in the development of some cancers.
iupac name: 2-chloro-N-(4-chloro-3-pyridin-2-ylphenyl)-4-methylsulfonylbenzamide
xref: CHEMBL473417
synonym: GDC-0449
synonym: HhAntag691
synonym: Erivedge®
approved: t
ligand name: vismodegib
type: SyntheticOrganicLigand

methyltestosterone
in ch i key: GCKMFJBGXUYNAG-HLXURNFRSA-N
in ch i: InChI=1S/C20H30O2/c1-18-9-6-14(21)12-13(18)4-5-15-16(18)7-10-19(2)17(15)8-11-20(19,3)22/h12,15-17,22H,4-11H2,1-3H3/t15-,16+,17+,18+,19+,20+/m1/s1
comment: Methyltestosterone is a synthetic anabolic steroid used for treating men with testosterone deficiency or similar androgen replacement therapies.
iupac name: (8R,9S,10R,13S,14S,17S)-17-hydroxy-10,13,17-trimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-3-one
xref: CHEMBL1395
synonym: Testred
synonym: 17-methyltestosterone
synonym: Virilon
synonym: Mesterone
approved: f
ligand name: methyltestosterone
type: SyntheticOrganicLigand

oxazine 89
in ch i key: MELQHVBGGSKVJQ-YJBOKZPZSA-N
in ch i: InChI=1S/C19H15F4N5O2/c1-18(7-15(19(21,22)23)30-17(25)28-18)12-6-11(3-4-13(12)20)27-16(29)14-5-2-10(8-24)9-26-14/h2-6,9,15H,7H2,1H3,(H2,25,28)(H,27,29)/t15-,18-/m0/s1
comment: The CF3-substituted 1,3, oxazine 89 was found by Roche to be an orally active BACE1 inhibitor with an excellent PD profile in mice and a long lasting Aβ40/42 reduction in the CSF of rats<Reference id=23498/> 13 PDB structures have been submitted and one of the series may enter clinical development
iupac name: N-{3-[(4S,6S)-2-amino-4-methyl-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-4-yl]-4-fluorophenyl}-5-cyanopyridine-2-carboxamide
xref: CHEMBL2347208
approved: f
ligand name: oxazine 89
type: SyntheticOrganicLigand

flutamide
canonical SMILES: O=C(C(C)C)Nc1ccc(c(c1)C(F)(F)F)[N+](=O)[O-]
isomeric SMILES: O=C(C(C)C)Nc1ccc(c(c1)C(F)(F)F)[N+](=O)[O-]
in ch i key: MKXKFYHWDHIYRV-UHFFFAOYSA-N
in ch i: InChI=1S/C11H11F3N2O3/c1-6(2)10(17)15-7-3-4-9(16(18)19)8(5-7)11(12,13)14/h3-6H,1-2H3,(H,15,17)
comment: Flutamide is an androgen receptor antagonist.
iupac name: 2-methyl-N-[4-nitro-3-(trifluoromethyl)phenyl]propanamide
xref: CHEMBL806
synonym: SCH-13521
synonym: Drogenil
synonym: Eulexin®
synonym: Flutamin
synonym: Cytomid
approved: t
ligand name: flutamide
type: SyntheticOrganicLigand

tolcapone
canonical SMILES: Cc1ccc(cc1)C(=O)c1cc(O)c(c(c1)[N+](=O)[O-])O
isomeric SMILES: Cc1ccc(cc1)C(=O)c1cc(O)c(c(c1)[N+](=O)[O-])O
in ch i key: MIQPIUSUKVNLNT-UHFFFAOYSA-N
in ch i: InChI=1S/C14H11NO5/c1-8-2-4-9(5-3-8)13(17)10-6-11(15(19)20)14(18)12(16)7-10/h2-7,16,18H,1H3
comment: Tolcapone is a selective, potent and reversible nitro catechol type inhibitor of enzyme catechol-O-methyl transferase (COMT). As a result of reported hepatoxicity complications tolcapone has been withdrawn from the market in a number of countries.
iupac name: (3,4-dihydroxy-5-nitrophenyl)-(4-methylphenyl)methanone
xref: CHEMBL1324
synonym: Ro 40-7592
synonym: Tasmar®
synonym: Ro-407592
approved: t
ligand name: tolcapone
type: SyntheticOrganicLigand

calcitonin (salmon)
in ch i key: AZCMZZXDDMAXIT-VJVYQDLKSA-N
comment: A synthetic calcitonin receptor agonist. Salmon calcitonin has actions identical to calcitonins of mammalian origin, but its potency is greater and it is longer acting. The overall effect of calcitonin treatment is an increase in bone mass.
xref: CHEMBL1201661
synonym: Fortical
synonym: Miacalcin®
approved: t
ligand name: calcitonin (salmon)
type: PeptideLigand

corticotropin zinc hydroxide
in ch i key: PNMZQWKBJIQQJL-FAUHKOHMSA-N
comment: This peptide is a melanocortin receptor 2 agonist. As a drug, use has been discontinued.
xref: CHEMBL1201609
synonym: ortrophin-Zinc
approved: t
ligand name: corticotropin zinc hydroxide
type: PeptideLigand

tazarotene
canonical SMILES: CCOC(=O)c1ccc(nc1)C#Cc1ccc2c(c1)C(C)(C)CCS2
isomeric SMILES: CCOC(=O)c1ccc(nc1)C#Cc1ccc2c(c1)C(C)(C)CCS2
in ch i key: OGQICQVSFDPSEI-UHFFFAOYSA-N
in ch i: InChI=1S/C21H21NO2S/c1-4-24-20(23)16-7-9-17(22-14-16)8-5-15-6-10-19-18(13-15)21(2,3)11-12-25-19/h6-7,9-10,13-14H,4,11-12H2,1-3H3
comment: Tazarotene is a vitamin A-like retinoid that binds all isoforms of the retinoic acid receptor, but may show selectivity for the β, and γ isoforms acting via which may result in altered gene expression that provides the beneficial effects on skin condition. Tazarotene is essentailly a prodrug, with tazarotenic acid (PubChem CID 147525) being the active metabolite.
iupac name: ethyl 6-[2-(4,4-dimethyl-2,3-dihydrothiochromen-6-yl)ethynyl]pyridine-3-carboxylate
xref: CHEMBL1657
synonym: Avage
synonym: Fabior
synonym: AGN-190168
synonym: Tazorac®
synonym: Zorac®
approved: t
ligand name: tazarotene
type: SyntheticOrganicLigand

3-iodothyronamine
canonical SMILES: NCCc1ccc(cc1)Oc1ccc(c(c1)I)O
isomeric SMILES: NCCc1ccc(cc1)Oc1ccc(c(c1)I)O
in ch i key: HCYGDNGLWSZCCA-UHFFFAOYSA-N
in ch i: InChI=1S/C14H14INO2/c15-13-9-12(5-6-14(13)17)18-11-3-1-10(2-4-11)7-8-16/h1-6,9,17H,7-8,16H2
comment: 3-Iodothyronamine is an endogenous thyronamine and derivative of thyroid hormone. It acts as a high-affinity ligand for the trace amine-associated receptor TAAR1 <Reference id=7006/><Reference id=7018/>.
iupac name: 4-[4-(2-aminoethyl)phenoxy]-2-iodophenol
xref: CHEMBL201002
synonym: T1AM
approved: f
ligand name: 3-iodothyronamine
type: MetaboliteLigand

dextrothyroxine
in ch i key: XUIIKFGFIJCVMT-GFCCVEGCSA-N
in ch i: InChI=1S/C15H11I4NO4/c16-8-4-7(5-9(17)13(8)21)24-14-10(18)1-6(2-11(14)19)3-12(20)15(22)23/h1-2,4-5,12,21H,3,20H2,(H,22,23)/t12-/m1/s1
comment: The INN record for this compound and the US FDA approval, are for the sodium salt. This drug is the dextrorotary isomer of synthetic thyroxine and acts as an antihyperlipidemic.
iupac name: (2R)-2-amino-3-[4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl]propanoic acid
xref: CHEMBL559
synonym: D-thyroxine
synonym: D-T4
synonym: Choloxin®
approved: t
ligand name: dextrothyroxine
type: SyntheticOrganicLigand

cosyntropin
in ch i key: ZOEFCCMDUURGSE-CQVUSSRSSA-N
comment: This is a synthetic peptide forming the fully active N-terminal portion of cortocotropin. Like the endogenous peptide, cosyntropin stimulates the adrenal cortex to produce and secrete adrenocortical hormones.
xref: CHEMBL2103784
synonym: Vicotrope
synonym: Cortrosyn®
approved: t
ligand name: cosyntropin
type: PeptideLigand

roflumilast
in ch i key: MNDBXUUTURYVHR-UHFFFAOYSA-N
comment: Roflumilast is a phosphodiesterase-4 inhibitor.
iupac name: 3-(CYCLOPROPYLMETHOXY)-N-(3,5-DICHLOROPYRIDIN-4-YL)-4-(DIFLUOROMETHOXY)BENZAMIDE
xref: CHEMBL193240
synonym: BY-217
synonym: BYK-20869
synonym: Daliresp®
synonym: Libertek
synonym: Daxas®
synonym: ARQ-151/Zoryve® (roflumilast cream)
approved: t
ligand name: roflumilast
type: SyntheticOrganicLigand

eltrombopag
isomeric SMILES: OC(=O)c1cccc(c1)c1cccc(c1O)N/N=C/1/C(=NN(C1=O)c1ccc(c(c1)C)C)C
in ch i key: XDXWLKQMMKQXPV-QYQHSDTDSA-N
in ch i: InChI=1S/C25H22N4O4/c1-14-10-11-19(12-15(14)2)29-24(31)22(16(3)28-29)27-26-21-9-5-8-20(23(21)30)17-6-4-7-18(13-17)25(32)33/h4-13,26,30H,1-3H3,(H,32,33)/b27-22-
comment: Eltrombopag is a thrombopoietin receptor agonist that increases production of platelets. The structure shown here represents the compound with double bond stereochemistry as stipulated in the INN record for this drug. Representations on other chemistry databases may show alternative tautomers. The marketed drug contains eltrombopag olamine (PubChem CID 71719015, again note tautomer difference).
iupac name: 3-(3-{2-[(4Z)-1-(3,4-dimethylphenyl)-3-methyl-5-oxo-4,5-dihydro-1H-pyrazol-4-ylidene]hydrazin-1-yl}-2-hydroxyphenyl)benzoic acid
xref: CHEMBL461101
synonym: AMG531
synonym: SB-497115-GR
synonym: Promacta®
synonym: Revolade®
approved: t
ligand name: eltrombopag
type: SyntheticOrganicLigand

anisindione
canonical SMILES: COc1ccc(cc1)C1C(=O)c2c(C1=O)cccc2
isomeric SMILES: COc1ccc(cc1)C1C(=O)c2c(C1=O)cccc2
in ch i key: XRCFXMGQEVUZFC-UHFFFAOYSA-N
in ch i: InChI=1S/C16H12O3/c1-19-11-8-6-10(7-9-11)14-15(17)12-4-2-3-5-13(12)16(14)18/h2-9,14H,1H3
comment: Anisindione is a synthetic anticoagulant which inhibits vitamin K-dependent gamma-carboxylase.
iupac name: 2-(4-methoxyphenyl)indene-1,3-dione
xref: CHEMBL712
synonym: Miradon®
approved: t
ligand name: anisindione
type: SyntheticOrganicLigand

danazol
in ch i key: POZRVZJJTULAOH-LHZXLZLDSA-N
in ch i: InChI=1S/C22H27NO2/c1-4-22(24)10-8-18-16-6-5-15-11-19-14(13-23-25-19)12-20(15,2)17(16)7-9-21(18,22)3/h1,11,13,16-18,24H,5-10,12H2,2-3H3/t16-,17+,18+,20+,21+,22+/m1/s1
comment: Danazol is a synthetic steroid with antigonadotropic and anti-estrogenic activities.
xref: CHEMBL1479
synonym: Chronogyn
synonym: Anatrol
synonym: Danocrine®
approved: t
ligand name: danazol
type: SyntheticOrganicLigand

TAK-070
in ch i key: SETMAZMOXYOEJA-NRFANRHFSA-N
in ch i: InChI=1S/C27H31NO/c1-28(2)17-16-21-8-13-26-19-27(15-14-25(26)18-21)29-20-22-9-11-24(12-10-22)23-6-4-3-5-7-23/h3-7,9-12,14-15,19,21H,8,13,16-18,20H2,1-2H3/t21-/m0/s1
comment: TAK-070 from Takeda shows partial reduction in Aβ as well as increase in sAPPα in animal models. The noncompetitive BACE1 inhibition may be sufficient to modify amyloid pathology and ameliorate cognitive deficits in Alzheimer's Diseases without causing potential adverse events by complete BACE1 ablation.<Reference id=23493/>
iupac name: N,N-dimethyl-2-[(2R)-6-[(4-phenylphenyl)methoxy]-1,2,3,4-tetrahydronaphthalen-2-yl]ethanamine
approved: f
ligand name: TAK-070
type: SyntheticOrganicLigand

tasosartan
in ch i key: ADXGNEYLLLSOAR-UHFFFAOYSA-N
in ch i: InChI=1S/C23H21N7O/c1-14-18-11-12-21(31)30(23(18)25-15(2)24-14)13-16-7-9-17(10-8-16)19-5-3-4-6-20(19)22-26-28-29-27-22/h3-10H,11-13H2,1-2H3,(H,26,27,28,29)
iupac name: 2,4-dimethyl-8-[[4-[2-(2H-tetrazol-5-yl)phenyl]phenyl]methyl]-5,6-dihydropyrido[6,5-d]pyrimidin-7-one
xref: CHEMBL432162
approved: f
ligand name: tasosartan
type: SyntheticOrganicLigand

tesamorelin
in ch i key: QBEPNUQJQWDYKU-BMGKTWPMSA-N
comment: This drug is a stabilized synthetic peptide analogue of the hypothalamic peptide GHRH. The approved formulation is the acetate salt. The chemical structure shown here was generated using the SMILES from PubChem CID 16137828.
xref: CHEMBL1237026
synonym: TH9507
synonym: (3E)-hex-3-enoylsomatoliberin
synonym: Egrifta®
approved: t
ligand name: tesamorelin
type: PeptideLigand

mitotane
canonical SMILES: ClC(C(c1ccccc1Cl)c1ccc(cc1)Cl)Cl
isomeric SMILES: ClC(C(c1ccccc1Cl)c1ccc(cc1)Cl)Cl
in ch i key: JWBOIMRXGHLCPP-UHFFFAOYSA-N
in ch i: InChI=1S/C14H10Cl4/c15-10-7-5-9(6-8-10)13(14(17)18)11-3-1-2-4-12(11)16/h1-8,13-14H
comment: The molecular mechanism underlying mitotane's clinical effects is complex and poorly understood <Reference id=30070/>.
iupac name: 1-chloro-4-[2,2-dichloro-1-(2-chlorophenyl)ethyl]benzene
xref: CHEMBL1670
synonym: CB-313
synonym: o,p'-DDD
synonym: Lysodren®
approved: t
ligand name: mitotane
type: SyntheticOrganicLigand

alpha-methyltyrosine
canonical SMILES: Oc1ccc(cc1)CC(C(=O)O)(N)C
isomeric SMILES: Oc1ccc(cc1)C[C@@](C(=O)O)(N)C
in ch i key: NHTGHBARYWONDQ-JTQLQIEISA-N
in ch i: InChI=1S/C10H13NO3/c1-10(11,9(13)14)6-7-2-4-8(12)5-3-7/h2-5,12H,6,11H2,1H3,(H,13,14)/t10-/m0/s1
comment: The US FDA approved name for this compound is metyrosine, an inhibitor of tyrosine 3-hydroxylase enzymatic activity.
iupac name: (2S)-2-amino-3-(4-hydroxyphenyl)-2-methylpropanoic acid
xref: CHEMBL1200862
synonym: MK-781
synonym: Metirosine
synonym: metyrosine
synonym: Demser®
approved: t
ligand name: alpha-methyltyrosine
type: SyntheticOrganicLigand

ecallantide
in ch i key: VBGWSQKGUZHFPS-VGMMZINCSA-N
comment: This 60 amino acid peptide drug is an inhibitor of human plasma kallikrein (KLKB1; P03952). The recombinant protein is produced in yeast (Pichia pastoris).The chemical structure shown here was generated using the SMILES from PubChem CID 44152182.
xref: CHEMBL1201837
synonym: DX-88
synonym: FOV2302
synonym: Kalbitor®
approved: t
ligand name: ecallantide
type: PeptideLigand

dextromethorphan
canonical SMILES: COc1ccc2c(c1)C13CCCCC3C(C2)N(CC1)C
in ch i key: MKXZASYAUGDDCJ-NJAFHUGGSA-N
in ch i: InChI=1S/C18H25NO/c1-19-10-9-18-8-4-3-5-15(18)17(19)11-13-6-7-14(20-2)12-16(13)18/h6-7,12,15,17H,3-5,8-11H2,1-2H3/t15-,17+,18+/m1/s1
comment: Dextromethorphan is a morphinan class sedative. It is available over-the-counter (OTC) for use as an antitussive. At doses much higher than medically recommended, dextromethorphan is used recreationally for its dissociative anesthetic and euphoria producing effects.
xref: CHEMBL52440
synonym: Delsym
synonym: Romilar
synonym: d-methorphan
approved: t
ligand name: dextromethorphan
type: SyntheticOrganicLigand

β-phenylethylamine
canonical SMILES: NCCc1ccccc1
isomeric SMILES: NCCc1ccccc1
in ch i key: BHHGXPLMPWCGHP-UHFFFAOYSA-N
in ch i: InChI=1S/C8H11N/c9-7-6-8-4-2-1-3-5-8/h1-5H,6-7,9H2
iupac name: 2-phenylethanamine
xref: CHEMBL610
synonym: 2-phenylethylamine
synonym: phenethylamine
synonym: β-PEA
approved: f
ligand name: β-phenylethylamine
type: MetaboliteLigand

compound 10 [PMID: 15482908]
canonical SMILES: N#Cc1cc(F)cc(c1)n1nnc(n1)c1[nH]cc(n1)C
isomeric SMILES: N#Cc1cc(F)cc(c1)n1nnc(n1)c1[nH]cc(n1)C
in ch i key: BKGULEDZLIMLMY-UHFFFAOYSA-N
in ch i: InChI=1S/C12H8FN7/c1-7-6-15-11(16-7)12-17-19-20(18-12)10-3-8(5-14)2-9(13)4-10/h2-4,6H,1H3,(H,15,16)
iupac name: 3-fluoro-5-[5-(4-methyl-1H-imidazol-2-yl)-2H-1,2,3,4-tetrazol-2-yl]benzonitrile
xref: CHEMBL186808
approved: f
ligand name: compound 10 [PMID: 15482908]
type: SyntheticOrganicLigand

compound 2 [PMID: 22911925]
in ch i key: IUSARDYWEPUTPN-OZBXUNDUSA-N
in ch i: InChI=1S/C33H44N4O4S/c1-21(40-5)29(39)37-26(16-22-8-6-9-24(14-22)31-34-12-13-42-31)28(38)20-35-27-18-33(10-7-11-33)41-30-25(27)15-23(19-36-30)17-32(2,3)4/h6,8-9,12-15,19,21,26-28,35,38H,7,10-11,16-18,20H2,1-5H3,(H,37,39)/t21-,26+,27+,28-/m1/s1
comment: A hydroxyethylamine-based inhibitor of BACE1 from Amgen capable of lowering Aβ levels in the brains of rats after oral administration <Reference id=23504/>. Also has a PDB structure <Reference id=23505/>.
iupac name: (2R)-N-[(2S,3R)-4-{[(4'S)-6'-(2,2-dimethylpropyl)-3',4'-dihydrospiro[cyclobutane-1,2'-pyrano[2,3-b]pyridine]-4'-yl]amino}-3-hydroxy-1-[3-(1,3-thiazol-2-yl)phenyl]butan-2-yl]-2-methoxypropanamide
xref: CHEMBL2181911
synonym: compound 37 [PMID: 22468684]
approved: f
ligand name: compound 2 [PMID: 22911925]
type: SyntheticOrganicLigand

nandrolone
canonical SMILES: O=C1CCC2C(=C1)CCC1C2CCC2(C1CCC2O)C
in ch i key: NPAGDVCDWIYMMC-IZPLOLCNSA-N
in ch i: InChI=1S/C18H26O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h10,13-17,20H,2-9H2,1H3/t13-,14+,15+,16-,17-,18-/m0/s1
comment: An androgen receptor agonist with associated anabolic properties. The INN record for nandrolone is for the core compound without the decanoate side chain, but other national commissions use nandrolone decanoate to name nadrolone. The first US FDA nandrolone based drug approval was for nandrolone phenpropionate in 1959, since then many formulations have been approved but subsequently discontinued. Our record for nandrolone is intended to cover various fomulations of the compound including nandrolone phenpropionate (PubChem CID 229455) and nandrolone decanoate (PubChem CID 9677).
iupac name: (8R,9S,10R,13S,14S,17S)-17-hydroxy-13-methyl-2,6,7,8,9,10,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-one
xref: CHEMBL757
synonym: Menidrabol
synonym: Retabolil
synonym: Nortestosterone decanoate
synonym: 19-norandrostenolone
synonym: Durabolin® (phenylpropionate ester)
synonym: Deca-Durabolin® (decanoate ester)
approved: t
ligand name: nandrolone
type: SyntheticOrganicLigand

ethylestrenol
canonical SMILES: CCC1(O)CCC2C1(C)CCC1C2CCC2=CCCCC12
in ch i key: AOXRBFRFYPMWLR-XGXHKTLJSA-N
in ch i: InChI=1S/C20H32O/c1-3-20(21)13-11-18-17-9-8-14-6-4-5-7-15(14)16(17)10-12-19(18,20)2/h6,15-18,21H,3-5,7-13H2,1-2H3/t15-,16+,17+,18-,19-,20-/m0/s1
comment: This drug is an anabolic steroid, derived from nandrolone.
iupac name: (8R,9S,10R,13S,14S,17S)-17-ethyl-13-methyl-2,3,6,7,8,9,10,11,12,14,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-17-ol
xref: CHEMBL1200623
synonym: Maxibolin®
synonym: Orabolin®
approved: t
ligand name: ethylestrenol
type: SyntheticOrganicLigand

dromostanolone propionate
in ch i key: NOTIQUSPUUHHEH-UXOVVSIBSA-N
in ch i: InChI=1S/C23H36O3/c1-5-21(25)26-20-9-8-17-16-7-6-15-12-19(24)14(2)13-23(15,4)18(16)10-11-22(17,20)3/h14-18,20H,5-13H2,1-4H3/t14-,15+,16+,17+,18+,20+,22+,23+/m1/s1
comment: This drug is a synthetic androgen with similar properties to testosterone. Drostanolone is used extensively (and illicitly) by athletes and bodybuilders aiming to build muscle strength and definition.
iupac name: [(2R,5S,8R,9S,10S,13S,14S,17S)-2,10,13-trimethyl-3-oxo-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl] propanoate
xref: CHEMBL1201048
synonym: drostanolone
synonym: Masterone
synonym: Masteron®
approved: t
ligand name: dromostanolone propionate
type: SyntheticOrganicLigand

compound 11d [PMID: 23981898]
in ch i key: FIUDDEQHPBHZBI-XPLIUGCLSA-N
comment: Novartis optmised BACE1 inhibitor (11d) with potent cellular activity (IC50 10 nM) and a PDB structure. A single oral dose of 60 μmol/kg effected significant reduction in brain Aβ in APP51/16 transgenic mice <Reference id=23499/>.
iupac name: (1R,3S,4S,5R)-3-[(4-amino-3-fluoro-5-{[(2R)-1,1,1-trifluoro-3-methoxypropan-2-yl]oxy}phenyl)methyl]-5-{[(3-tert-butylphenyl)methyl]amino}-4-hydroxy-1λ4-thian-1-one
xref: CHEMBL2425612
approved: f
ligand name: compound 11d [PMID: 23981898]
type: SyntheticOrganicLigand

vanillylmandelic acid
canonical SMILES: COc1cc(ccc1O)C(C(=O)O)O
isomeric SMILES: COc1cc(ccc1O)C(C(=O)O)O
in ch i key: CGQCWMIAEPEHNQ-UHFFFAOYSA-N
in ch i: InChI=1S/C9H10O5/c1-14-7-4-5(2-3-6(7)10)8(11)9(12)13/h2-4,8,10-11H,1H3,(H,12,13)
iupac name: 2-hydroxy-2-(4-hydroxy-3-methoxyphenyl)acetic acid
xref: CHEMBL1256396
approved: f
ligand name: vanillylmandelic acid
type: MetaboliteLigand

AZ-4217
in ch i key: TUGLMYZSOPKJOA-PMERELPUSA-N
in ch i: InChI=1S/C30H25FN4O/c1-4-8-20-14-22(17-33-16-20)21-9-6-10-23(15-21)30(24-13-19(3)29(36)35(5-2)18-24)25-11-7-12-26(31)27(25)28(32)34-30/h6-7,9-18H,5H2,1-3H3,(H2,32,34)/t30-/m0/s1
comment: AZ-4217 is a potent BACE1 inhibitor for Alzheimer's Disease with efficacy in mice, guinea pigs, and Tg2576 mice <Reference id=23483/>. There is a BACE1 PDB structure with this ligand 4B00 but with a different tautomeric representation as PubChem CID 60210950
iupac name: 5-[(1R)-3-amino-4-fluoro-1-{3-[5-(prop-1-yn-1-yl)pyridin-3-yl]phenyl}-1H-isoindol-1-yl]-1-ethyl-3-methyl-1,2-dihydropyridin-2-one
xref: CHEMBL2152903
synonym: AZ4217
synonym: AZ 4217
approved: f
ligand name: AZ-4217
type: SyntheticOrganicLigand

LY2119620
in ch i key: TYTGOXSAAQWLPJ-UHFFFAOYSA-N
iupac name: 3-amino-5-chloro-N-cyclopropyl-4-methyl-6-[2-(4-methylpiperazin-1-yl)-2-oxoethoxy]thieno[2,3-b]pyridine-2-carboxamide
synonym: LY 2119620
synonym: LY-2119620
approved: f
ligand name: LY2119620
type: SyntheticOrganicLigand

iperoxo
canonical SMILES: C[N+](CC#CCOC1=NOCC1)(C)C
isomeric SMILES: C[N+](CC#CCOC1=NOCC1)(C)C
in ch i key: WXXOCGISBCTWPW-UHFFFAOYSA-N
in ch i: InChI=1S/C10H17N2O2/c1-12(2,3)7-4-5-8-13-10-6-9-14-11-10/h6-9H2,1-3H3/q+1
iupac name: 4-(4,5-dihydro-1,2-oxazol-3-yloxy)but-2-ynyl-trimethylazanium
xref: CHEMBL3121473
approved: f
ligand name: iperoxo
type: SyntheticOrganicLigand

LY2811376
canonical SMILES: NC1=NC(CCS1)(C)c1cc(c2cncnc2)c(cc1F)F
in ch i key: MJQMRGWYPNIERM-HNNXBMFYSA-N
in ch i: InChI=1S/C15H14F2N4S/c1-15(2-3-22-14(18)21-15)11-4-10(12(16)5-13(11)17)9-6-19-8-20-7-9/h4-8H,2-3H2,1H3,(H2,18,21)/t15-/m0/s1
comment: LY2811376 is a non-peptidic BACE1 inhibitor for Alzheimer's Disease. Aβ reductions in lumbar CSF were measured after oral dosing in humans but development was halted because of toxicology findings but these may not be related to BACE1 inhibition.
iupac name: (4S)-4-[2,4-difluoro-5-(pyrimidin-5-yl)phenyl]-4-methyl-5,6-dihydro-4H-1,3-thiazin-2-amine
xref: CHEMBL2333941
synonym: LY 2811376
synonym: LY-2811376
approved: f
ligand name: LY2811376
type: SyntheticOrganicLigand

AZD3839
in ch i key: QXKYWSDUVAJHNZ-CGAIIQECSA-N
in ch i: InChI=1S/C24H18F3N5/c25-19-6-2-5-18-21(19)23(28)32-24(18,17-7-8-31-20(10-17)22(26)27)16-4-1-3-14(9-16)15-11-29-13-30-12-15/h1-13,22-23,32H,28H2/t23?,24-/m0/s1
comment: AstraZeneca BACE1 inhibitor AZD3839 recently progressed into Phase 1 clinical trials for Alzheimer's Disease.
iupac name: (3S)-3-[2-(difluoromethyl)pyridin-4-yl]-7-fluoro-3-[3-(pyrimidin-5-yl)phenyl]-2,3-dihydro-1H-isoindol-1-amine
synonym: AZD-3839
synonym: AZD 3839
approved: f
ligand name: AZD3839
type: SyntheticOrganicLigand

ABT-288
in ch i key: GNIRITULTPTAQW-KNQAVFIVSA-N
in ch i: InChI=1S/C23H24N4O/c1-25-15-19-12-14-26(22(19)16-25)20-8-4-17(5-9-20)18-6-10-21(11-7-18)27-23(28)3-2-13-24-27/h2-11,13,19,22H,12,14-16H2,1H3/t19-,22+/m1/s1
comment: ABT-288 is a competitive antagonist with high affinity and selectivity for H3 receptors that enhances the release of acetylcholine and dopamine in rat prefrontal cortex. Has been studied for cognitive impairment associated with Alzheimer’s disease and schizophrenia but is now one of the NCATS repurposing compounds <Reference id=23441/>
iupac name: 2-[4-[4-[(3aR,6aR)-5-methyl-2,3,3a,4,6,6a-hexahydropyrrolo[3,2-c]pyrrol-1-yl]phenyl]phenyl]pyridazin-3-one
synonym: ABT 288
synonym: ABT288
approved: f
ligand name: ABT-288
type: SyntheticOrganicLigand

encenicline
canonical SMILES: O=C(c1cc2c(s1)c(Cl)ccc2)NC1CN2CCC1CC2
in ch i key: SSRDSYXGYPJKRR-ZDUSSCGKSA-N
in ch i: InChI=1S/C16H17ClN2OS/c17-12-3-1-2-11-8-14(21-15(11)12)16(20)18-13-9-19-6-4-10(13)5-7-19/h1-3,8,10,13H,4-7,9H2,(H,18,20)/t13-/m0/s1
comment: This compound was developed as part of EnVivo Pharmaceuticals alpha-7 agonist program <Reference id=23426/>. The compound exhibits good brain penetration and an adequate exposure time for clinical utility <Reference id=23426/>. EnVivo changed its name to FORUM Pharmaceuticals Inc. in April 2014.
iupac name: N-[(3R)-1-azabicyclo[2.2.2]octan-3-yl]-7-chloro-1-benzothiophene-2-carboxamide
xref: CHEMBL2151572
synonym: EVP-6124
synonym: EVP 6124
synonym: EVP6124
approved: f
ligand name: encenicline
type: SyntheticOrganicLigand

SN-38
in ch i key: FJHBVJOVLFPMQE-QFIPXVFZSA-N
in ch i: InChI=1S/C22H20N2O5/c1-3-12-13-7-11(25)5-6-17(13)23-19-14(12)9-24-18(19)8-16-15(20(24)26)10-29-21(27)22(16,28)4-2/h5-8,25,28H,3-4,9-10H2,1-2H3/t22-/m0/s1
comment: Active metabolite of irinotecan
iupac name: (19S)-10,19-diethyl-7,19-dihydroxy-17-oxa-3,13-diazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(21),2(11),3,5,7,9,15(20)-heptaene-14,18-dione
xref: CHEMBL837
synonym: SN 38 lactone
approved: f
ligand name: SN-38
type: SyntheticOrganicLigand

18-HETE
canonical SMILES: CCC(CCC=CCC=CCC=CCC=CCCCC(=O)O)O
isomeric SMILES: CCC(CC/C=C/C/C=C/C/C=C/C/C=C/CCCC(=O)O)O
in ch i key: PPCHNRUZQWLEMF-XBOCNYGYSA-N
in ch i: InChI=1S/C20H32O3/c1-2-19(21)17-15-13-11-9-7-5-3-4-6-8-10-12-14-16-18-20(22)23/h4-7,10-13,19,21H,2-3,8-9,14-18H2,1H3,(H,22,23)/b6-4-,7-5-,12-10-,13-11-
iupac name: (5Z,8Z,11Z,14Z)-18-hydroxyicosa-5,8,11,14-tetraenoic acid
approved: f
ligand name: 18-HETE
type: MetaboliteLigand

16-HETE
canonical SMILES: CCCCC(C=CCC=CCC=CCC=CCCCC(=O)O)O
isomeric SMILES: CCCCC(/C=C/C/C=C/C/C=C/C/C=C/CCCC(=O)O)O
in ch i key: JEKNPVYFNMZRJG-UFINWASNSA-N
in ch i: InChI=1S/C20H32O3/c1-2-3-16-19(21)17-14-12-10-8-6-4-5-7-9-11-13-15-18-20(22)23/h4-5,8-11,14,17,19,21H,2-3,6-7,12-13,15-16,18H2,1H3,(H,22,23)/b5-4-,10-8-,11-9-,17-14-
iupac name: (5Z,8Z,11Z,14Z)-16-hydroxyicosa-5,8,11,14-tetraenoic acid
approved: f
ligand name: 16-HETE
type: MetaboliteLigand

12-hydroxylauric acid
canonical SMILES: OCCCCCCCCCCCC(=O)O
isomeric SMILES: OCCCCCCCCCCCC(=O)O
in ch i key: ZDHCZVWCTKTBRY-UHFFFAOYSA-N
in ch i: InChI=1S/C12H24O3/c13-11-9-7-5-3-1-2-4-6-8-10-12(14)15/h13H,1-11H2,(H,14,15)
iupac name: 12-Hydroxydodecanoic acid
xref: CHEMBL55068
approved: f
ligand name: 12-hydroxylauric acid
type: MetaboliteLigand

calcifediol
in ch i key: JWUBBDSIWDLEOM-DTOXIADCSA-N
in ch i: InChI=1S/C27H44O2/c1-19-10-13-23(28)18-22(19)12-11-21-9-7-17-27(5)24(14-15-25(21)27)20(2)8-6-16-26(3,4)29/h11-12,20,23-25,28-29H,1,6-10,13-18H2,2-5H3/b21-11+,22-12-/t20-,23+,24-,25+,27-/m1/s1
comment: 25-hydroxyvitamin D3 is the major circulating metabolite of 25-hydroxyvitamin D. Calcifediol is the WHO INN for the same compound.
iupac name: (1S,3Z)-3-[(2E)-2-[(1R,3aS,7aR)-1-[(2R)-6-hydroxy-6-methylheptan-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylidenecyclohexan-1-ol
xref: CHEMBL1040
synonym: U-32070E
synonym: Calderol
synonym: 25-hydroxyvitamin D3
synonym: Ryaldee®
synonym: calcidiol
approved: t
ligand name: calcifediol
type: MetaboliteLigand

benzolamide
canonical SMILES: O=S(=O)(c1ccccc1)Nc1nnc(s1)S(=O)(=O)N
isomeric SMILES: O=S(=O)(c1ccccc1)Nc1nnc(s1)S(=O)(=O)N
in ch i key: PWDGTQXZLNDOKS-UHFFFAOYSA-N
in ch i: InChI=1S/C8H8N4O4S3/c9-18(13,14)8-11-10-7(17-8)12-19(15,16)6-4-2-1-3-5-6/h1-5H,(H,10,12)(H2,9,13,14)
comment: An experimental carbonic anhydrase inhibitor
iupac name: 5-(phenylsulfonylamino)-1,3,4-thiadiazole-2-sulfonamide
xref: CHEMBL73962
approved: f
ligand name: benzolamide
type: SyntheticOrganicLigand

prunetin
canonical SMILES: COc1cc(O)c2c(c1)occ(c2=O)c1ccc(cc1)O
isomeric SMILES: COc1cc(O)c2c(c1)occ(c2=O)c1ccc(cc1)O
in ch i key: KQMVAGISDHMXJJ-UHFFFAOYSA-N
in ch i: InChI=1S/C16H12O5/c1-20-11-6-13(18)15-14(7-11)21-8-12(16(15)19)9-2-4-10(17)5-3-9/h2-8,17-18H,1H3
comment: An aldehyde dehydrogenase inhibitor
iupac name: 5-hydroxy-3-(4-hydroxyphenyl)-7-methoxychromen-4-one
xref: CHEMBL491174
synonym: 4',5-dihydroxy-7-methoxyisoflavone
approved: f
ligand name: prunetin
type: SyntheticOrganicLigand

compound 21 [PMID: 22802221]
in ch i key: XTEOJPUYZWEXFI-UHFFFAOYSA-N
in ch i: InChI=1S/C23H29N3O4S2/c1-4-5-12-30-23(27)25-32(28,29)22-21(14-20(31-22)13-17(2)3)19-8-6-18(7-9-19)15-26-11-10-24-16-26/h6-11,14,16-17H,4-5,12-13,15H2,1-3H3,(H,25,27)
comment: Compound 21 is a first-in-class orally administered angiotensin AT2 receptor agonist. It prevents TNFα-induced and HFD-induced vascular inflammation in vitro and in vivo, indicating that its anti-atherosclerotic actions are due to vascular anti-inflammatory effects, mediated by AT2 receptors <Reference id=31356/>. C21 is one of the chemical structures that are claimed in Vicore Pharma's patent US20180078529A1 <Reference id=43626/>.
iupac name: butyl N-[3-[4-(imidazol-1-ylmethyl)phenyl]-5-(2-methylpropyl)thiophen-2-yl]sulfonylcarbamate
xref: CHEMBL189568
synonym: C21
synonym: 3-[4-(1H-imidazol-1-ylmethyl)phenyl]-5-(2-methylpropyl)thiophene-2-[(N-butyloxylcarbamate)-sulphonamide] sodium salt
approved: f
ligand name: compound 21 [PMID: 22802221]
type: SyntheticOrganicLigand

5-butyl-methyl immidazole carboxylate 30
canonical SMILES: CCCCc1cnc(n1Cc1ccc(cc1)c1ccccc1C)C(=O)O
isomeric SMILES: CCCCc1cnc(n1Cc1ccc(cc1)c1ccccc1C)C(=O)O
in ch i key: ZCAMCVJTCSXPMT-UHFFFAOYSA-N
in ch i: InChI=1S/C22H24N2O2/c1-3-4-8-19-14-23-21(22(25)26)24(19)15-17-10-12-18(13-11-17)20-9-6-5-7-16(20)2/h5-7,9-14H,3-4,8,15H2,1-2H3,(H,25,26)
iupac name: 5-butyl-1-[[4-(2-methylphenyl)phenyl]methyl]imidazole-2-carboxylic acid
synonym: compound 30 [PMID: 22889560]
approved: f
ligand name: 5-butyl-methyl immidazole carboxylate 30
type: SyntheticOrganicLigand

5-oxo-1-2-4-oxadiazol biphenyl
in ch i key: FXELTRKWYHPHAE-IBGZPJMESA-N
in ch i: InChI=1S/C23H25N3O5/c1-3-7-19(22(28)29)26(20(27)4-2)14-15-10-12-16(13-11-15)17-8-5-6-9-18(17)21-24-23(30)31-25-21/h5-6,8-13,19H,3-4,7,14H2,1-2H3,(H,28,29)(H,24,25,30)/t19-/m0/s1
iupac name: (2S)-2-[[4-[2-(5-oxo-2H-1,2,4-oxadiazol-3-yl)phenyl]phenyl]methyl-propanoylamino]pentanoic acid
synonym: compound 1c [PMID: 22410249]
approved: f
ligand name: 5-oxo-1-2-4-oxadiazol biphenyl
type: SyntheticOrganicLigand

metanephrine
canonical SMILES: CNCC(c1ccc(c(c1)OC)O)O
isomeric SMILES: CNCC(c1ccc(c(c1)OC)O)O
in ch i key: JWJCTZKFYGDABJ-UHFFFAOYSA-N
in ch i: InChI=1S/C10H15NO3/c1-11-6-9(13)7-3-4-8(12)10(5-7)14-2/h3-5,9,11-13H,6H2,1-2H3
iupac name: 4-(1-hydroxy-2-methylaminoethyl)-2-methoxyphenol
xref: CHEMBL775
synonym: metadrenaline
approved: f
ligand name: metanephrine
type: MetaboliteLigand

ibrutinib
in ch i key: XYFPWWZEPKGCCK-GOSISDBHSA-N
in ch i: InChI=1S/C25H24N6O2/c1-2-21(32)30-14-6-7-18(15-30)31-25-22(24(26)27-16-28-25)23(29-31)17-10-12-20(13-11-17)33-19-8-4-3-5-9-19/h2-5,8-13,16,18H,1,6-7,14-15H2,(H2,26,27,28)/t18-/m1/s1
comment: Ibrutinib is a clinically used inhibitor of Bruton's tyrosine kinase. It was originally approved with breakthrough therapy designation through the FDA's accelerated approval program.
iupac name: 1-[(3R)-3-[4-amino-3-(4-phenoxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]piperidin-1-yl]prop-2-en-1-one
xref: CHEMBL1873475
synonym: PCI-32765
synonym: Imbruvica®
approved: t
ligand name: ibrutinib
type: SyntheticOrganicLigand

N,N`-bis-alkyl butylimmidazole 12b
in ch i key: BFASNXRKCVRLPK-UHFFFAOYSA-M
in ch i: InChI=1S/C35H29N10.BrH.2Na/c1-2-3-12-33-32(21-24-13-17-26(18-14-24)28-8-4-6-10-30(28)34-37-41-42-38-34)36-23-45(33)22-25-15-19-27(20-16-25)29-9-5-7-11-31(29)35-39-43-44-40-35;;;/h4-11,13-20H,2-3,12,21-22H2,1H3;1H;;/q-1;;2*+1/p-1
comment: The representation of this compoound on PubChem shows a different tautomer, linked to above.
iupac name: disodium;5-[2-[4-[[4-butyl-3-[[4-[2-(1,2,4-triaza-3-azanidacyclopenta-1,4-dien-5-yl)phenyl]phenyl]methyl]-1H-imidazol-3-ium-5-yl]methyl]phenyl]phenyl]-1,2,4-triaza-3-azanidacyclopenta-1,4-diene;bromide
synonym: compound 12b [PMID: 23376252]
approved: f
ligand name: N,N`-bis-alkyl butylimmidazole 12b
type: SyntheticOrganicLigand

LY303336
in ch i key: HHFYOGBTLFTWQX-QTJGBDASSA-N
in ch i: InChI=1S/C30H34N4O10S/c1-2-3-4-5-9-23(33-17-26(31-18-33)32-27(35)22-8-6-7-10-25(22)45(41,42)43)28(36)34-16-21(15-24(34)30(39)40)44-20-13-11-19(12-14-20)29(37)38/h6-8,10-14,17-18,21,23-24H,2-5,9,15-16H2,1H3,(H,32,35)(H,37,38)(H,39,40)(H,41,42,43)/t21-,23+,24-/m0/s1
iupac name: (2S,4S)-4-(4-carboxyphenoxy)-1-[(2R)-2-[4-[(2-sulfobenzoyl)amino]imidazol-1-yl]octanoyl]pyrrolidine-2-carboxylic acid
xref: CHEMBL344662
synonym: LY 303336
synonym: LY-303336
approved: f
ligand name: LY303336
type: SyntheticOrganicLigand

dicumarol
in ch i key: DOBMPNYZJYQDGZ-UHFFFAOYSA-N
in ch i: InChI=1S/C19H12O6/c20-16-10-5-1-3-7-14(10)24-18(22)12(16)9-13-17(21)11-6-2-4-8-15(11)25-19(13)23/h1-8,20-21H,9H2
comment: Vitamin K epoxide reductase complex subunit 1 isoform 1 inhibitor
iupac name: 4-hydroxy-3-[(4-hydroxy-2-oxo-2H-chromen-3-yl)methyl]-2H-chromen-2-one
xref: CHEMBL1466
synonym: Antitrombosin
synonym: Baracoumin
synonym: Cuma
synonym: Cumid
synonym: Acadyl
synonym: Acavyl
synonym: Dicoumal
synonym: bishydroxycoumarin
synonym: Melitoxin®
approved: t
ligand name: dicumarol
type: SyntheticOrganicLigand

pemetrexed
in ch i key: WBXPDJSOTKVWSJ-CYBMUJFWSA-N
in ch i: InChI=1S/C20H21N5O6/c21-20-24-16-15(18(29)25-20)12(9-22-16)6-3-10-1-4-11(5-2-10)17(28)23-13(19(30)31)7-8-14(26)27/h1-2,4-5,9,13H,3,6-8H2,(H,23,28)(H,26,27)(H,30,31)(H4,21,22,24,25,29)/t13-/m1/s1
comment: Inhibits dihydrofolate reductase, GAR transformylase and thymidylate synthase. Marketed formulations may contain pemetrexed disodium (PubChem CID 46931002).
iupac name: (2R)-2-[[4-[2-(2-amino-4-oxo-1,7-dihydropyrrolo[4,5-e]pyrimidin-5-yl)ethyl]benzoyl]amino]pentanedioic acid
xref: CHEMBL1201258
synonym: Alimta®
synonym: LY-231514
approved: t
ligand name: pemetrexed
type: SyntheticOrganicLigand

LY301875
in ch i key: HHFYOGBTLFTWQX-XWGVYQGASA-N
in ch i: InChI=1S/C30H34N4O10S/c1-2-3-4-5-9-23(33-17-26(31-18-33)32-27(35)22-8-6-7-10-25(22)45(41,42)43)28(36)34-16-21(15-24(34)30(39)40)44-20-13-11-19(12-14-20)29(37)38/h6-8,10-14,17-18,21,23-24H,2-5,9,15-16H2,1H3,(H,32,35)(H,37,38)(H,39,40)(H,41,42,43)/t21-,23-,24-/m0/s1
comment: The structure of LY301875 shown here is the same as that in the reference listed <Reference id=23265/>. Please note that the stereochemistry of the ChEMBL entry linked to above varies slightly from our structure.
iupac name: (2S,4S)-4-(4-carboxyphenoxy)-1-[(2S)-2-[4-[(2-sulfobenzoyl)amino]imidazol-1-yl]octanoyl]pyrrolidine-2-carboxylic acid
synonym: LY 301875
synonym: LY-301875
approved: f
ligand name: LY301875
type: SyntheticOrganicLigand

[3H]irbesartan
in ch i key: YOSHYTLCDANDAN-UHFFFAOYSA-N
in ch i: InChI=1S/C25H28N6O/c1-2-3-10-22-26-25(15-6-7-16-25)24(32)31(22)17-18-11-13-19(14-12-18)20-8-4-5-9-21(20)23-27-29-30-28-23/h4-5,8-9,11-14H,2-3,6-7,10,15-17H2,1H3,(H,27,28,29,30)
comment: The position of the tritiated hydrogen atom is unspecified by the reference describing this compound and so the radiolabel is not shown in this structure.
iupac name: 2-butyl-3-[[4-[2-(2H-tetrazol-5-yl)phenyl]phenyl]methyl]-1,3-diazaspiro[4.4]non-1-en-4-one
xref: CHEMBL1513
approved: f
ligand name: [3H]irbesartan
type: SyntheticOrganicLigand

[3H]candesartan
in ch i key: HTQMVQVXFRQIKW-UHFFFAOYSA-N
in ch i: InChI=1S/C24H20N6O3/c1-2-33-24-25-20-9-5-8-19(23(31)32)21(20)30(24)14-15-10-12-16(13-11-15)17-6-3-4-7-18(17)22-26-28-29-27-22/h3-13H,2,14H2,1H3,(H,31,32)(H,26,27,28,29)
comment: The position of the tritiated hydrogen atom is unspecified by the reference describing this compound and so the radiolabel is not shown in this structure.
iupac name: 2-ethoxy-3-[[4-[2-(2H-tetrazol-5-yl)phenyl]phenyl]methyl]benzimidazole-4-carboxylic acid
xref: CHEMBL1016
approved: f
ligand name: [3H]candesartan
type: SyntheticOrganicLigand

TRV027
in ch i key: XIEWFECSPPTVQN-KMIMAYJXSA-N
in ch i: InChI=1S/C43H67N13O10/c1-7-24(4)35(40(63)53-31(19-27-20-47-22-49-27)41(64)56-17-9-11-32(56)38(61)50-25(5)42(65)66)55-37(60)30(18-26-12-14-28(57)15-13-26)52-39(62)34(23(2)3)54-36(59)29(51-33(58)21-46-6)10-8-16-48-43(44)45/h12-15,20,22-25,29-32,34-35,46,57H,7-11,16-19,21H2,1-6H3,(H,47,49)(H,50,61)(H,51,58)(H,52,62)(H,53,63)(H,54,59)(H,55,60)(H,65,66)(H4,44,45,48)/t24-,25+,29-,30-,31-,32-,34-,35-/m0/s1
comment: TRV027 (TRV120027) is a synthetic analogue of endogenous angiotensin II peptide <Reference id=23306/>. It acts as a β-arrestin biased ligand of the angiotensin II type 1 receptor (AT1R). TRV027 inhibits angiotensin II-mediated vasoconstriction, increases cardiomyocyte contractility and induces an anti-apoptotic effect, all of which when combined, provide a cardioprotective result.
xref: CHEMBL4297447
synonym: TRV120027
synonym: TRV-120027
synonym: TRV-027
synonym: TRV 120027
approved: f
ligand name: TRV027
type: PeptideLigand

azilsartan
in ch i key: KGSXMPPBFPAXLY-UHFFFAOYSA-N
in ch i: InChI=1S/C25H20N4O5/c1-2-33-24-26-20-9-5-8-19(23(30)31)21(20)29(24)14-15-10-12-16(13-11-15)17-6-3-4-7-18(17)22-27-25(32)34-28-22/h3-13H,2,14H2,1H3,(H,30,31)(H,27,28,32)
comment: The active form of the approved drug azilsartan medoxomil.
iupac name: 2-ethoxy-3-[[4-[2-(5-oxo-2H-1,2,4-oxadiazol-3-yl)phenyl]phenyl]methyl]benzimidazole-4-carboxylic acid
xref: CHEMBL57242
synonym: TAK536
synonym: TAK 536
synonym: TAK-536
approved: f
ligand name: azilsartan
type: SyntheticOrganicLigand

azilsartan medoxomil
in ch i key: QJFSABGVXDWMIW-UHFFFAOYSA-N
in ch i: InChI=1S/C30H24N4O8/c1-3-38-28-31-23-10-6-9-22(27(35)39-16-24-17(2)40-30(37)41-24)25(23)34(28)15-18-11-13-19(14-12-18)20-7-4-5-8-21(20)26-32-29(36)42-33-26/h4-14H,3,15-16H2,1-2H3,(H,32,33,36)
comment: Azilsartan medoxomil is metabolised into the active form azilsartan. The azilsartan ligand page (accessed via the link above) contains more details of the drug's clinical use and mechanistic action. The marketed brand, Edarbi®, contains azilsartan medoxomil potassium (PubChem CID 23699544).
iupac name: (5-methyl-2-oxo-1,3-dioxol-4-yl)methyl 2-ethoxy-3-[[4-[2-(5-oxo-2H-1,2,4-oxadiazol-3-yl)phenyl]phenyl]methyl]benzimidazole-4-carboxylate
xref: CHEMBL2028661
synonym: TAK 491
synonym: Edarbi®
approved: t
ligand name: azilsartan medoxomil
type: SyntheticOrganicLigand

saprisartan
in ch i key: DUEWVPTZCSAMNB-UHFFFAOYSA-N
iupac name: 3-[[3-bromo-2-[2-(trifluoromethylsulfonylamino)phenyl]-1-benzofuran-5-yl]methyl]-5-cyclopropyl-2-ethylimidazole-4-carboxamide
xref: CHEMBL305544
synonym: GR-138950
synonym: GR 138950
synonym: GR138950
approved: f
ligand name: saprisartan
type: SyntheticOrganicLigand

forasartan
in ch i key: YONOBYIBNBCDSJ-UHFFFAOYSA-N
in ch i: InChI=1S/C23H28N8/c1-3-5-11-21-25-22(12-6-4-2)31(28-21)16-17-13-14-20(24-15-17)18-9-7-8-10-19(18)23-26-29-30-27-23/h7-10,13-15H,3-6,11-12,16H2,1-2H3,(H,26,27,29,30)
comment: Forasartan is a nonpeptide, competitive and reversible angiotensin II receptor antagonist, selective for the AT1 receptor. Forasartan is not a popular drug of choice for hypertension as it is less effective than <Ligand id=590/>, due to its relatively short duration of action.
iupac name: 5-[(3,5-dibutyl-1,2,4-triazol-1-yl)methyl]-2-[2-(2H-tetrazol-5-yl)phenyl]pyridine
xref: CHEMBL315021
synonym: SC-52458
approved: t
ligand name: forasartan
type: SyntheticOrganicLigand

L-163,101
in ch i key: BRUYKNQQCIYYNP-UHFFFAOYSA-N
in ch i: InChI=1S/C34H36N4O3S/c1-6-31-36-32-23(4)19-24(5)35-33(32)38(31)21-25-12-15-27(16-13-25)29-20-26(18-22(2)3)14-17-30(29)42(40,41)37-34(39)28-10-8-7-9-11-28/h7-17,19-20,22H,6,18,21H2,1-5H3,(H,37,39)
iupac name: N-[2-[4-[(2-ethyl-5,7-dimethylimidazo[4,5-b]pyridin-3-yl)methyl]phenyl]-4-(2-methylpropyl)phenyl]sulfonylbenzamide
synonym: L-163101
approved: f
ligand name: L-163,101
type: SyntheticOrganicLigand

angiotensin A
in ch i key: CHCOFDZSJYMQMX-NOQNJSOHSA-N
in ch i: InChI=1S/C49H71N13O10/c1-6-28(4)40(46(69)58-36(24-32-25-53-26-55-32)47(70)62-21-11-15-38(62)44(67)59-37(48(71)72)23-30-12-8-7-9-13-30)61-43(66)35(22-31-16-18-33(63)19-17-31)57-45(68)39(27(2)3)60-42(65)34(56-41(64)29(5)50)14-10-20-54-49(51)52/h7-9,12-13,16-19,25-29,34-40,63H,6,10-11,14-15,20-24,50H2,1-5H3,(H,53,55)(H,56,64)(H,57,68)(H,58,69)(H,59,67)(H,60,65)(H,61,66)(H,71,72)(H4,51,52,54)/t28-,29-,34-,35-,36-,37-,38-,39-,40-/m0/s1
synonym: ang A
approved: f
ligand name: angiotensin A
type: PeptideLigand

novokinin
in ch i key: WCJSVACAALWGRF-LQPYQXOBSA-N
in ch i: InChI=1S/C39H61N11O7/c1-23(2)20-29(47-34(52)31-14-8-18-49(31)36(54)26(41)11-7-17-44-39(42)43)33(51)46-28(13-5-6-16-40)37(55)50-19-9-15-32(50)35(53)48-30(38(56)57)21-24-22-45-27-12-4-3-10-25(24)27/h3-4,10,12,22-23,26,28-32,45H,5-9,11,13-21,40-41H2,1-2H3,(H,46,51)(H,47,52)(H,48,53)(H,56,57)(H4,42,43,44)/t26-,28-,29-,30-,31-,32-/m0/s1
approved: f
ligand name: novokinin
type: PeptideLigand

warfarin
canonical SMILES: CC(=O)CC(c1c(=O)oc2c(c1O)cccc2)c1ccccc1
isomeric SMILES: CC(=O)CC(c1c(=O)oc2c(c1O)cccc2)c1ccccc1
in ch i key: PJVWKTKQMONHTI-UHFFFAOYSA-N
in ch i: InChI=1S/C19H16O4/c1-12(20)11-15(13-7-3-2-4-8-13)17-18(21)14-9-5-6-10-16(14)23-19(17)22/h2-10,15,21H,11H2,1H3
comment: PubChem CID 54678486 is an enatiomeric mixture of the much more active S-form (CID 54688261) and the R-form (CID 54684598) <Reference id=28545/>. This reference also reviews important pharmacogenomic aspects of this drug but note the application of this has become controversial (see the PharmKB drug link). Note also there is also a tautomeric variant depicted as CID 54689812. Marketed formulations may specify warfarin sodium (CID 16204922) or warfarin potassium (CID 23706212).
iupac name: 4-hydroxy-3-(3-oxo-1-phenylbutyl)-2H-chromen-2-one
xref: CHEMBL1464
synonym: Athrombin
synonym: Athrombin-K
synonym: Co-Rax
synonym: Coumafen
synonym: Coumadin®
synonym: Jantoven
synonym: panwarfin
synonym: Marevan®
approved: t
ligand name: warfarin
type: SyntheticOrganicLigand

vorinostat
canonical SMILES: ONC(=O)CCCCCCC(=O)Nc1ccccc1
isomeric SMILES: ONC(=O)CCCCCCC(=O)Nc1ccccc1
in ch i key: WAEXFXRVDQXREF-UHFFFAOYSA-N
in ch i: InChI=1S/C14H20N2O3/c17-13(15-12-8-4-3-5-9-12)10-6-1-2-7-11-14(18)16-19/h3-5,8-9,19H,1-2,6-7,10-11H2,(H,15,17)(H,16,18)
comment: Vorinostat inhibits Class I, II and IV histone deacetylases (our pages for HDACs are available using this link).
iupac name: N-hydroxy-N'-phenyloctanediamide
xref: CHEMBL98
synonym: MK-0683
synonym: MK0683
synonym: suberoylanilide hydroxamic acid
synonym: Zolinza®
synonym: SAHA
approved: t
ligand name: vorinostat
type: SyntheticOrganicLigand

vinblastine
in ch i key: JXLYSJRDGCGARV-CFWMRBGOSA-N
in ch i: InChI=1S/C46H58N4O9/c1-8-42(54)23-28-24-45(40(52)57-6,36-30(15-19-49(25-28)26-42)29-13-10-11-14-33(29)47-36)32-21-31-34(22-35(32)56-5)48(4)38-44(31)17-20-50-18-12-16-43(9-2,37(44)50)39(59-27(3)51)46(38,55)41(53)58-7/h10-14,16,21-22,28,37-39,47,54-55H,8-9,15,17-20,23-26H2,1-7H3/t28-,37-,38+,39+,42-,43+,44+,45-,46-/m0/s1
comment: A pan tubulin inhibitor. A chemical analogue of <Ligand id=6785/> (from Catharanthus roseus, also known as Vinca rosea). There is some ambiguity surrounding the exact stereochemistry of vinblastine. The chirality shown here corresponds to the PubChem entry linked to in the table above. However, bioactivity data for the compound is also listed against CID 241903, and some of the links in the table above refer to this chiral specification or others. Marketed formulations contain vinblastine sulfate (PubChem CID 5388983).
xref: CHEMBL159
synonym: 29060-LE
synonym: Rozevin
synonym: Velban®
synonym: vincaleucoblastin
synonym: vincaleukoblastine
synonym: Velbe®
approved: t
ligand name: vinblastine
type: SyntheticOrganicLigand

trilostane
in ch i key: KVJXBPDAXMEYOA-CXANFOAXSA-N
in ch i: InChI=1S/C20H27NO3/c1-18-7-6-14-12(13(18)3-4-15(18)22)5-8-20-17(24-20)16(23)11(10-21)9-19(14,20)2/h12-15,17,22-23H,3-9H2,1-2H3/t12-,13-,14-,15-,17+,18-,19+,20+/m0/s1
comment: Trilostane is a 3 β-hydroxysteroid dehydrogenase (gene symbol HSD3B1) inhibitor. It is now used mainly in veterinary practice.
xref: CHEMBL1200907
synonym: Modrastane
synonym: Modrenal
synonym: Desopan
synonym: WIN-24540
synonym: WIN 24,540
synonym: Vetoryl®
approved: t
ligand name: trilostane
type: SyntheticOrganicLigand

topiramate
in ch i key: KJADKKWYZYXHBB-XBWDGYHZSA-N
in ch i: InChI=1S/C12H21NO8S/c1-10(2)18-7-5-16-12(6-17-22(13,14)15)9(8(7)19-10)20-11(3,4)21-12/h7-9H,5-6H2,1-4H3,(H2,13,14,15)/t7-,8-,9+,12+/m1/s1
comment: A multifunctional compound: inhibits carbonic anhydrases II and IV, positively modulates GABA-A receptor anion channels, blocks sodium channel alpha subunits and behaves as an antagonist at the ionotropic glutamate receptors (AMPA and kainate).
iupac name: [(3aS,5aR,8aR,8bS)-2,2,7,7-tetramethyl-5,5a,8a,8b-tetrahydrodi[1,3]dioxolo[4,5-a:5',3'-d]pyran-3a-yl]methyl sulfamate
xref: CHEMBL220492
synonym: MCN-4853
synonym: RWJ-17021
synonym: epitomax
synonym: Topamax®
synonym: Eprontia® (liquid formulation)
approved: t
ligand name: topiramate
type: SyntheticOrganicLigand

tolbutamide
canonical SMILES: CCCCNC(=O)NS(=O)(=O)c1ccc(cc1)C
isomeric SMILES: CCCCNC(=O)NS(=O)(=O)c1ccc(cc1)C
in ch i key: JLRGJRBPOGGCBT-UHFFFAOYSA-N
in ch i: InChI=1S/C12H18N2O3S/c1-3-4-9-13-12(15)14-18(16,17)11-7-5-10(2)6-8-11/h5-8H,3-4,9H2,1-2H3,(H2,13,14,15)
comment: A sulfonylurea family drug inhibiting sulfonylurea receptor 1 (ABCC8)/Kir6.2 ( KCNJ11).
iupac name: 3-butyl-1-(4-methylbenzenesulfonyl)urea
xref: CHEMBL782
synonym: Diabetol
synonym: Artosin
synonym: Diaben
synonym: Butamide
synonym: Diabetamid
synonym: Dolipol
synonym: Orabet
synonym: Rastinon
synonym: Orinase®
synonym: tolbutamide sodium
approved: t
ligand name: tolbutamide
type: SyntheticOrganicLigand

tolazamide
canonical SMILES: O=C(NS(=O)(=O)c1ccc(cc1)C)NN1CCCCCC1
isomeric SMILES: O=C(NS(=O)(=O)c1ccc(cc1)C)NN1CCCCCC1
in ch i key: OUDSBRTVNLOZBN-UHFFFAOYSA-N
in ch i: InChI=1S/C14H21N3O3S/c1-12-6-8-13(9-7-12)21(19,20)16-14(18)15-17-10-4-2-3-5-11-17/h6-9H,2-5,10-11H2,1H3,(H2,15,16,18)
comment: A sulfonylurea family drug inhibiting sulfonylurea receptor 1 (ABCC8)/Kir6.2 (KCNJ11) potassium channel activity.
iupac name: 1-(azepan-1-yl)-3-(4-methylbenzenesulfonyl)urea
xref: CHEMBL817
synonym: tolazolamide
synonym: Norglycin
synonym: Tolanase
synonym: Diabewas
synonym: Tolinase®
approved: t
ligand name: tolazamide
type: SyntheticOrganicLigand

thioguanine
canonical SMILES: Nc1nc(=S)c2c([nH]1)nc[nH]2
isomeric SMILES: Nc1nc(=S)c2c([nH]1)nc[nH]2
in ch i key: WYWHKKSPHMUBEB-UHFFFAOYSA-N
in ch i: InChI=1S/C5H5N5S/c6-5-9-3-2(4(11)10-5)7-1-8-3/h1H,(H4,6,7,8,9,10,11)
comment: Inhibits inosine-5'-monophosphate dehydrogenase 1.
iupac name: 2-amino-6,7-dihydro-3H-purine-6-thione
xref: CHEMBL727
synonym: 6-mercaptoguanine
synonym: 6-thioguanine
synonym: Lanvis®
synonym: Tabloid®
approved: t
ligand name: thioguanine
type: SyntheticOrganicLigand

teriflunomide
canonical SMILES: N#CC(=C(O)C)C(=O)Nc1ccc(cc1)C(F)(F)F
isomeric SMILES: N#C/C(=C(/O)/C)/C(=O)Nc1ccc(cc1)C(F)(F)F
in ch i key: UTNUDOFZCWSZMS-YFHOEESVSA-N
in ch i: InChI=1S/C12H9F3N2O2/c1-7(18)10(6-16)11(19)17-9-4-2-8(3-5-9)12(13,14)15/h2-5,18H,1H3,(H,17,19)/b10-7-
comment: Teriflunomide inhibits dihydroorotate dehydrogenase (DHODH). It is the active metabolite of <Ligand id=6825/>.
iupac name: (Z)-2-cyano-3-hydroxy-N-[4-(trifluoromethyl)phenyl]but-2-enamide
xref: CHEMBL973
synonym: Aubagio®
synonym: HMR-1726
synonym: A77 1726
synonym: flucyamide
approved: t
ligand name: teriflunomide
type: SyntheticOrganicLigand

brinzolamide
in ch i key: HCRKCZRJWPKOAR-JTQLQIEISA-N
in ch i: InChI=1S/C12H21N3O5S3/c1-3-14-10-8-15(5-4-6-20-2)23(18,19)12-9(10)7-11(21-12)22(13,16)17/h7,10,14H,3-6,8H2,1-2H3,(H2,13,16,17)/t10-/m0/s1
comment: Carbonic anhydrase inhibitor
iupac name: (4R)-4-ethylamino-2-(3-methoxypropyl)-1,1-dioxo-3,4-dihydrothieno[4,5-e]thiazine-6-sulfonamide
xref: CHEMBL220491
synonym: AL-4862
synonym: Azopt®
approved: t
ligand name: brinzolamide
type: SyntheticOrganicLigand

teniposide
in ch i key: NRUKOCRGYNPUPR-QBPJDGROSA-N
in ch i: InChI=1S/C32H32O13S/c1-37-19-6-13(7-20(38-2)25(19)33)23-14-8-17-18(42-12-41-17)9-15(14)28(16-10-39-30(36)24(16)23)44-32-27(35)26(34)29-21(43-32)11-40-31(45-29)22-4-3-5-46-22/h3-9,16,21,23-24,26-29,31-35H,10-12H2,1-2H3/t16-,21+,23+,24-,26+,27+,28+,29+,31+,32-/m0/s1
comment: A podophyllotoxin derivative which achieves cytotoxicity by inhibiting type II topoisomerase activity. Many (85) isomeric alternatives for this compound are listed on PubChem. Click here to link directly to the PubChem listing. The structure shown here matches that shown in the INN document for this compound.
iupac name: (5S,5aR,8aR,9R)-5-[[(2R,4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-thiophen-2-yl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-6-yl]oxy]-9-(4-hydroxy-3,5-dimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[6,5-f][1,3]benzodioxol-8-one
xref: CHEMBL452231
synonym: VM-26
synonym: Vehem
synonym: Vee M-26
synonym: Vumon®
synonym: isosulfan blue
approved: t
ligand name: teniposide
type: SyntheticOrganicLigand

ribavirin
canonical SMILES: OCC1OC(C(C1O)O)n1cnc(n1)C(=O)N
in ch i key: IWUCXVSUMQZMFG-AFCXAGJDSA-N
in ch i: InChI=1S/C8H12N4O5/c9-6(16)7-10-2-12(11-7)8-5(15)4(14)3(1-13)17-8/h2-5,8,13-15H,1H2,(H2,9,16)/t3-,4-,5-,8-/m1/s1
comment: Inhibits inosine-5'-monophosphate dehydrogenase 1 and RNA and also inhibits hepatitis C virus RNA-dependent RNA polymerase (NS5B).
iupac name: 1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,4-triazole-3-carboxamide
xref: CHEMBL1643
synonym: Rebetol®
synonym: Ribasphere
synonym: Ribav
synonym: Copegus®
synonym: ribofluranosyl carboxamide
synonym: Tribavirin
synonym: Viramid
synonym: Ribapak
synonym: Virazole®
approved: t
ligand name: ribavirin
type: SyntheticOrganicLigand

repaglinide
in ch i key: FAEKWTJYAYMJKF-QHCPKHFHSA-N
in ch i: InChI=1S/C27H36N2O4/c1-4-33-25-17-20(12-13-22(25)27(31)32)18-26(30)28-23(16-19(2)3)21-10-6-7-11-24(21)29-14-8-5-9-15-29/h6-7,10-13,17,19,23H,4-5,8-9,14-16,18H2,1-3H3,(H,28,30)(H,31,32)/t23-/m0/s1
comment: A sulfonylurea receptor 1, Kir6.2 blocker, belonging to the metiglinides drug family.
iupac name: 2-ethoxy-4-[2-[[(1S)-3-methyl-1-(2-piperidin-1-ylphenyl)butyl]amino]-2-oxoethyl]benzoic acid
xref: CHEMBL1272
synonym: (-)-repaglinide
synonym: AGEE-623ZW
synonym: Novonorm
synonym: Gluconorm
synonym: Prandin®
synonym: Enyglid
approved: t
ligand name: repaglinide
type: SyntheticOrganicLigand

pralatrexate
in ch i key: OGSBUKJUDHAQEA-WMCAAGNKSA-N
in ch i: InChI=1S/C23H23N7O5/c1-2-3-14(10-15-11-26-20-18(27-15)19(24)29-23(25)30-20)12-4-6-13(7-5-12)21(33)28-16(22(34)35)8-9-17(31)32/h1,4-7,11,14,16H,3,8-10H2,(H,28,33)(H,31,32)(H,34,35)(H4,24,25,26,29,30)/t14?,16-/m0/s1
comment: Inhibits dihydrofolate reductase, GAR transformylase and thymidylate synthase. The INN document specifies that pralatrexate is a racemic mixture of two epimers. These epimers are represented by the PubChem entries CID 23230419 and CID 11155808. We do not specify stereochemistry at the carbon atom which determines the two epimers, therefore our image represents the mixture. SARS-CoV-2 and COVID-19: Pralatrexate has been identified as an inhibitor of the viral RNA-dependent RNA polymerase (RdRp; nsp12) from SARS-CoV-2 <Reference id=41120/>. This translates to inhibition of SARS-CoV-2 replication in vitro (EC50 8 nM). Structural anaylsis suggests that the interaction points between pralatrexate and RdRp are distinct from those between <Ligand id=10715/> and RdRp.
iupac name: (2S)-2-[[4-[1-(2,4-diaminopteridin-6-yl)pent-4-yn-2-yl]benzoyl]amino]pentanedioic acid
xref: CHEMBL1201746
synonym: Folotyn®
synonym: PDX
approved: t
ligand name: pralatrexate
type: SyntheticOrganicLigand

phenprocoumon
canonical SMILES: CCC(c1c(=O)oc2c(c1O)cccc2)c1ccccc1
isomeric SMILES: CCC(c1c(=O)oc2c(c1O)cccc2)c1ccccc1
in ch i key: DQDAYGNAKTZFIW-UHFFFAOYSA-N
in ch i: InChI=1S/C18H16O3/c1-2-13(12-8-4-3-5-9-12)16-17(19)14-10-6-7-11-15(14)21-18(16)20/h3-11,13,19H,2H2,1H3
comment: Vitamin K epoxide reductase complex subunit 1 isoform 1 inhibitor. The INN-designated compound is a racemic mixture of two enantiomers.The structure shown here does not specify stereochemistry and represents the mixture.
iupac name: 4-hydroxy-3-(1-phenylpropyl)-2H-chromen-2-one
synonym: Liquamar®
synonym: phenprocoumarol
approved: t
ligand name: phenprocoumon
type: SyntheticOrganicLigand

phenindione
canonical SMILES: O=C1C(c2ccccc2)C(=O)c2c1cccc2
isomeric SMILES: O=C1C(c2ccccc2)C(=O)c2c1cccc2
in ch i key: NFBAXHOPROOJAW-UHFFFAOYSA-N
in ch i: InChI=1S/C15H10O2/c16-14-11-8-4-5-9-12(11)15(17)13(14)10-6-2-1-3-7-10/h1-9,13H
comment: Vitamin K epoxide reductase complex subunit 1 isoform 1 inhibitor
iupac name: 2-phenyl-2,3-dihydro-1H-indene-1,3-dione
xref: CHEMBL711
synonym: Hedulin
synonym: phenylindanedione
synonym: Dindevan®
approved: t
ligand name: phenindione
type: SyntheticOrganicLigand

pegaptanib
in ch i key: WLCZTRVUXYALDD-IBGZPJMESA-N
in ch i: InChI=1S/C22H44N3O10P/c1-31-15-17-33-21(27)24-13-9-7-11-19(25-22(28)34-18-16-32-2)20(26)23-12-8-5-4-6-10-14-35-36(3,29)30/h19H,4-18H2,1-3H3,(H,23,26)(H,24,27)(H,25,28)(H,29,30)/t19-/m0/s1
comment: Note that the PubChem CID listed here represents only the backbone of the molecule and does not include the nucleic acid aptamer attached to the phosphate group. Acts as a vascular endothelial growth factor A antagonist.
iupac name: 7-[[(2S)-2,6-bis(2-methoxyethoxycarbonylamino)hexanoyl]amino]heptoxy-methylphosphinic acid
synonym: EYEOO1
synonym: NX183
synonym: Macugen®
synonym: pegaptanib sodium
approved: t
ligand name: pegaptanib
type: SyntheticOrganicLigand

oxiglutatione
in ch i key: YPZRWBKMTBYPTK-BJDJZHNGSA-N
comment: The approved drug in this case is Navstel®. Oxiglutatione is listed as the active ingredient. Inhibits glutathione reductase. Note that the chemical structure given by DrugBank has opposite stereochemistry to the INN record and the ChEMBL ligand mapped here.
iupac name: (2S)-2-amino-4-{[(1R)-2-{[(2R)-2-[(4S)-4-amino-4-carboxybutanamido]-2-[(carboxymethyl)carbamoyl]ethyl]disulfanyl}-1-[(carboxymethyl)carbamoyl]ethyl]carbamoyl}butanoic acid
xref: CHEMBL1372
synonym: glutathione disulfide
synonym: Navstel®
approved: t
ligand name: oxiglutatione
type: SyntheticOrganicLigand

nitisinone
canonical SMILES: O=C1CCCC(=O)C1C(=O)c1ccc(cc1[N+](=O)[O-])C(F)(F)F
isomeric SMILES: O=C1CCCC(=O)C1C(=O)c1ccc(cc1[N+](=O)[O-])C(F)(F)F
in ch i key: OUBCNLGXQFSTLU-UHFFFAOYSA-N
in ch i: InChI=1S/C14H10F3NO5/c15-14(16,17)7-4-5-8(9(6-7)18(22)23)13(21)12-10(19)2-1-3-11(12)20/h4-6,12H,1-3H2
comment: Inhibits 4-hydroxyphenylpyruvate dioxygenase (HPD)
iupac name: 2-[2-nitro-4-(trifluoromethyl)benzoyl]cyclohexane-1,3-dione
xref: CHEMBL1337
synonym: Orfadin®
synonym: SC-0735
approved: t
ligand name: nitisinone
type: SyntheticOrganicLigand

nateglinide
canonical SMILES: CC(C1CCC(CC1)C(=O)NC(C(=O)O)Cc1ccccc1)C
in ch i key: OELFLUMRDSZNSF-BRWVUGGUSA-N
in ch i: InChI=1S/C19H27NO3/c1-13(2)15-8-10-16(11-9-15)18(21)20-17(19(22)23)12-14-6-4-3-5-7-14/h3-7,13,15-17H,8-12H2,1-2H3,(H,20,21)(H,22,23)/t15-,16-,17-/m1/s1
comment: A sulfonylurea receptor 1, Kir6.2 blocker, but belonging to the metiglinides drug family. Note that the PubChem CID listed here is a slightly different isomer to the ChEMBL ligand and the INN structure.
iupac name: (2R)-3-phenyl-2-{[(1r,4r)-4-(propan-2-yl)cyclohexyl]formamido}propanoic acid
xref: CHEMBL783
synonym: nateglinide
synonym: Fastic
synonym: Starsis
synonym: Trazec
synonym: Starlix®
synonym: SDZ-DJN-608
synonym: AY-4166
approved: t
ligand name: nateglinide
type: SyntheticOrganicLigand

mycophenolic acid
isomeric SMILES: COc1c(C/C=C(/CCC(=O)O)/C)c(O)c2c(c1C)COC2=O
in ch i key: HPNSFSBZBAHARI-RUDMXATFSA-N
in ch i: InChI=1S/C17H20O6/c1-9(5-7-13(18)19)4-6-11-15(20)14-12(8-23-17(14)21)10(2)16(11)22-3/h4,20H,5-8H2,1-3H3,(H,18,19)/b9-4+
comment: An antibacterial substance derived from Penicillium stoloniferum, and related species. Inhibits inosine-5'-monophosphate dehydrogenase (IMPDH).
iupac name: (E)-6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1H-2-benzofuran-5-yl)-4-methylhex-4-enoic acid
xref: CHEMBL866
synonym: ERL-080
synonym: Melbrex
synonym: Myfortic® (mycophenolate sodium)
approved: t
ligand name: mycophenolic acid
type: NaturalProductLigand

mycophenolate mofetil
isomeric SMILES: COc1c(C/C=C(/CCC(=O)OCCN2CCOCC2)/C)c(O)c2c(c1C)COC2=O
in ch i key: RTGDFNSFWBGLEC-SYZQJQIISA-N
in ch i: InChI=1S/C23H31NO7/c1-15(5-7-19(25)30-13-10-24-8-11-29-12-9-24)4-6-17-21(26)20-18(14-31-23(20)27)16(2)22(17)28-3/h4,26H,5-14H2,1-3H3/b15-4+
comment: Inhibits inosine-5'-monophosphate dehydrogenase (IMPDH)
iupac name: 2-(morpholin-4-yl)ethyl (4E)-6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl)-4-methylhex-4-enoate
xref: CHEMBL1456
synonym: Munoloc
synonym: Cellcept®
synonym: RS-61443-190
synonym: RS-61443
approved: t
ligand name: mycophenolate mofetil
type: SyntheticOrganicLigand

monobenzone
canonical SMILES: Oc1ccc(cc1)OCc1ccccc1
isomeric SMILES: Oc1ccc(cc1)OCc1ccccc1
in ch i key: VYQNWZOUAUKGHI-UHFFFAOYSA-N
in ch i: InChI=1S/C13H12O2/c14-12-6-8-13(9-7-12)15-10-11-4-2-1-3-5-11/h1-9,14H,10H2
comment: A tyrosinase inhibitor
iupac name: 4-(benzyloxy)phenol
xref: CHEMBL1388
synonym: Benoquin
synonym: Agerite
synonym: Carmifal
synonym: Depigman
synonym: p-benzyloxyphenol
approved: t
ligand name: monobenzone
type: SyntheticOrganicLigand

methocarbamol
canonical SMILES: COc1ccccc1OCC(COC(=O)N)O
isomeric SMILES: COc1ccccc1OCC(COC(=O)N)O
in ch i key: GNXFOGHNGIVQEH-UHFFFAOYSA-N
in ch i: InChI=1S/C11H15NO5/c1-15-9-4-2-3-5-10(9)16-6-8(13)7-17-11(12)14/h2-5,8,13H,6-7H2,1H3,(H2,12,14)
comment: Methocarbamol is the carbamate of <Ligand id=7617/>, but the carbamate bond is not metabolically hydrolysed, so guaifenesin is not a metabolite of methocarbamol. Methocarbamol has reduced abuse potential compared to other carbamate drugs such as <Ligand id=7225/> and its prodrug <Ligand id=7610/>.
iupac name: 2-hydroxy-3-(2-methoxyphenoxy)propyl carbamate
xref: CHEMBL1201117
synonym: Robaxin®
synonym: Forbaxin
synonym: Etroflex
synonym: Avetil
synonym: Delaxin
synonym: Robaxin-750
synonym: Parabaxin
approved: t
ligand name: methocarbamol
type: SyntheticOrganicLigand

methazolamide
canonical SMILES: CC(=O)N=c1sc(nn1C)S(=O)(=O)N
isomeric SMILES: CC(=O)N=c1sc(nn1C)S(=O)(=O)N
in ch i key: FLOSMHQXBMRNHR-UHFFFAOYSA-N
in ch i: InChI=1S/C5H8N4O3S2/c1-3(10)7-4-9(2)8-5(13-4)14(6,11)12/h1-2H3,(H2,6,11,12)
comment: Inhibits carbonic anhydrases. This compound is also represented on ChEMBL by the entry with ID CHEMBL19.
iupac name: N-(3-methyl-5-sulfamoyl-2,3-dihydro-1,3,4-thiadiazol-2-ylidene)acetamide
xref: CHEMBL1335656
synonym: Neptazane®
synonym: methenamide
approved: t
ligand name: methazolamide
type: SyntheticOrganicLigand

mequinol
canonical SMILES: COc1ccc(cc1)O
isomeric SMILES: COc1ccc(cc1)O
in ch i key: NWVVVBRKAWDGAB-UHFFFAOYSA-N
in ch i: InChI=1S/C7H8O2/c1-9-7-4-2-6(8)3-5-7/h2-5,8H,1H3
comment: A tyrosinase inhibitor
iupac name: 4-methoxyphenol
xref: CHEMBL544
synonym: 4-hydroxyanisole
synonym: p-hydroxyanisole
synonym: BMS-181158
synonym: Leucodine B
synonym: Leucobasal®
approved: t
ligand name: mequinol
type: SyntheticOrganicLigand

levetiracetam
canonical SMILES: CCC(N1CCCC1=O)C(=O)N
isomeric SMILES: CC[C@H](N1CCCC1=O)C(=O)N
in ch i key: HPHUVLMMVZITSG-LURJTMIESA-N
in ch i: InChI=1S/C8H14N2O2/c1-2-6(8(9)12)10-5-3-4-7(10)11/h6H,2-5H2,1H3,(H2,9,12)/t6-/m0/s1
comment: In addition to being assigned an INN in its own right, levetiracetam is the biologically active enantiomer of racemic formulation etiracetam, also assigned an INN. Levetiracetam is the active compound in Spritam®, the first 3D printed pill to be approved by the US FDA (in August 2015).
iupac name: (2S)-2-(2-oxopyrrolidin-1-yl)butanamide
xref: CHEMBL1286
synonym: Spritam®
synonym: Matever
synonym: Keppra®
synonym: UCB-L 059
synonym: UCB L059
approved: t
ligand name: levetiracetam
type: SyntheticOrganicLigand

leflunomide
canonical SMILES: O=C(c1cnoc1C)Nc1ccc(cc1)C(F)(F)F
isomeric SMILES: O=C(c1cnoc1C)Nc1ccc(cc1)C(F)(F)F
in ch i key: VHOGYURTWQBHIL-UHFFFAOYSA-N
in ch i: InChI=1S/C12H9F3N2O2/c1-7-10(6-16-19-7)11(18)17-9-4-2-8(3-5-9)12(13,14)15/h2-6H,1H3,(H,17,18)
comment: Inhibits dihydroorotate dehydrogenase.
iupac name: 5-methyl-N-[4-(trifluoromethyl)phenyl]-1,2-oxazole-4-carboxamide
xref: CHEMBL960
synonym: Arava®
synonym: SU-101
synonym: HWA-486
synonym: HWA 486
synonym: lefunamide
synonym: Sulol
synonym: Arabloc®
synonym: Lunava
synonym: Repso
approved: t
ligand name: leflunomide
type: SyntheticOrganicLigand

ixabepilone
in ch i key: FABUFPQFXZVHFB-PVYNADRNSA-N
in ch i: InChI=1S/C27H42N2O5S/c1-15-9-8-10-27(7)22(34-27)12-20(16(2)11-19-14-35-18(4)28-19)29-23(31)13-21(30)26(5,6)25(33)17(3)24(15)32/h11,14-15,17,20-22,24,30,32H,8-10,12-13H2,1-7H3,(H,29,31)/b16-11+/t15-,17+,20-,21-,22-,24-,27+/m0/s1
comment: A pan tubulin inhibitor. This compound is an analogue of a natural substance produced by Sorangium cellulosum and acts to stabilise microtubules.
iupac name: (1R,5S,6S,7R,10S,14S,16S)-6,10-dihydroxy-1,5,7,9,9-pentamethyl-14-[(E)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-17-oxa-13-azabicyclo[14.1.0]heptadecane-8,12-dione
xref: CHEMBL1201752
synonym: BMS-247550-01
synonym: azaepothilone B
synonym: BMS 247550-1
synonym: BMS-247550
synonym: Ixempra®
approved: t
ligand name: ixabepilone
type: SyntheticOrganicLigand

irinotecan
in ch i key: UWKQSNNFCGGAFS-XIFFEERXSA-N
in ch i: InChI=1S/C33H38N4O6/c1-3-22-23-16-21(43-32(40)36-14-10-20(11-15-36)35-12-6-5-7-13-35)8-9-27(23)34-29-24(22)18-37-28(29)17-26-25(30(37)38)19-42-31(39)33(26,41)4-2/h8-9,16-17,20,41H,3-7,10-15,18-19H2,1-2H3/t33-/m0/s1
comment: Irinotecan is a semisynthetic analogue of the natural plant alkaloid camptothecin (PubChem CID 24360) which functions as a DNA replication inhibitor by binding to topoisomerase I/DNA complexes <Reference id=29692/>. Camptothecin was first isolated from the bark and stem of Camptotheca acuminata, the Chinsese happy tree. The PubChem CID linked here is the same isomer as recorded in irinotecan's INN record.
xref: CHEMBL481
synonym: Onivyde®
synonym: biotecan
synonym: (+)-irinotecan
synonym: irinotecan hydrochloride
synonym: Irinotecan, Cpt-11
synonym: Camptosar®
synonym: CPT-11
synonym: Campto®
approved: t
ligand name: irinotecan
type: SyntheticOrganicLigand

hydroxyurea
canonical SMILES: NC(=O)NO
isomeric SMILES: NC(=O)NO
in ch i key: VSNHCAURESNICA-UHFFFAOYSA-N
in ch i: InChI=1S/CH4N2O2/c2-1(4)3-5/h5H,(H3,2,3,4)
comment: Inhibits ribonucleoside-diphosphate reductase (RR1).
iupac name: hydroxyurea
xref: CHEMBL467
synonym: Siklos®
synonym: Xromi®
synonym: Biosupressin
synonym: Hidrix
synonym: Hydura
synonym: Hydurea
synonym: Litaler
synonym: Litalir
synonym: Onco-Carbide
synonym: Hydrea®
synonym: Droxia®
synonym: hydroxycarbamide
synonym: SQ-1089
approved: t
ligand name: hydroxyurea
type: SyntheticOrganicLigand

glipizide
in ch i key: ZJJXGWJIGJFDTL-UHFFFAOYSA-N
in ch i: InChI=1S/C21H27N5O4S/c1-15-13-24-19(14-23-15)20(27)22-12-11-16-7-9-18(10-8-16)31(29,30)26-21(28)25-17-5-3-2-4-6-17/h7-10,13-14,17H,2-6,11-12H2,1H3,(H,22,27)(H2,25,26,28)
comment: A sulfonylurea family drug inhibiting sulfonylurea receptor 1 (ABCC8)/Kir6.2 (KCNJ11).
xref: CHEMBL1073
synonym: Aldiab
synonym: Digrin
synonym: Dipazide
synonym: Glibenese
synonym: Glibetin
synonym: Glican
synonym: Glide
synonym: Glidiab
synonym: Glipid
synonym: glupitel
synonym: glydiazinamide
synonym: melizide
synonym: zidia
synonym: Glucotrol®
synonym: K-4024
synonym: CP-28720
approved: t
ligand name: glipizide
type: SyntheticOrganicLigand

glimepiride
in ch i key: WIGIZIANZCJQQY-RUCARUNLSA-N
in ch i: InChI=1S/C24H34N4O5S/c1-4-21-17(3)15-28(22(21)29)24(31)25-14-13-18-7-11-20(12-8-18)34(32,33)27-23(30)26-19-9-5-16(2)6-10-19/h7-8,11-12,16,19H,4-6,9-10,13-15H2,1-3H3,(H,25,31)(H2,26,27,30)/t16-,19-
comment: Only approved by the EMA (2007) to be used in combination with pioglitazone (Tandemact®). Note that the PubChem CID listed above refers to the non-isomeric molecule. We show the isomeric form which corresponds to the structure held with the INN record for this compound.
xref: CHEMBL1481
synonym: Amarel
synonym: Endial
synonym: Novo-Glimepiride
synonym: Pms-Glimepiride
synonym: Ratio-Glimepiride
synonym: Amaryl®
synonym: glimepride
synonym: HOE-490
synonym: Sugral®
approved: t
ligand name: glimepiride
type: SyntheticOrganicLigand

compound 7 [PMID: 22533316]
in ch i key: MUXRZYNIEMIEAL-IYARVYRRSA-N
in ch i: InChI=1S/C22H33F3N2O3/c1-3-27(14-15-28)16-18-6-4-17(5-7-18)12-13-26(2)21(29)30-20-10-8-19(9-11-20)22(23,24)25/h8-11,17-18,28H,3-7,12-16H2,1-2H3/t17-,18-
comment: The structure of this compound was taken from the article which describes its discovery <Reference id=23084/>. PubChem CID 10127223 shows the non-chiral molecule.
iupac name: 4-(trifluoromethyl)phenyl N-methyl-N-{2-[(1r,4r)-4-{[ethyl(2-hydroxyethyl)amino]methyl}cyclohexyl]ethyl}carbamate
xref: CHEMBL2219824
approved: f
ligand name: compound 7 [PMID: 22533316]
type: SyntheticOrganicLigand

fondaparinux
in ch i key: KANJSNBRCNMZMV-ABRZTLGGSA-N
comment: Synthetic pentasaccharide Factor Xa inhibitor (via ATIII binding). The ChEMBL and PubChem links given here are without the sodium ions contained in the INN structure of this compound. Database entries include the sodium salt (e.g. PubChem CID 636380).
iupac name: (2R,3S,4S,5R,6R)-3-{[(2R,3R,4R,5R,6R)-5-{[(2R,3R,4R,5S,6S)-6-carboxy-5-{[(2R,3R,4R,5S,6R)-4,5-dihydroxy-3-(sulfoamino)-6-[(sulfooxy)methyl]oxan-2-yl]oxy}-3,4-dihydroxyoxan-2-yl]oxy}-3-(sulfoamino)-4-(sulfooxy)-6-[(sulfooxy)methyl]oxan-2-yl]oxy}-4-hydroxy-6-{[(2R,3S,4R,5R,6S)-4-hydroxy-6-methoxy-5-(sulfoamino)-2-[(sulfooxy)methyl]oxan-3-yl]oxy}-5-(sulfooxy)oxane-2-carboxylic acid
xref: CHEMBL1201202
synonym: Arixtra®
approved: t
ligand name: fondaparinux
type: SyntheticOrganicLigand

finasteride
in ch i key: DBEPLOCGEIEOCV-WSBQPABSSA-N
in ch i: InChI=1S/C23H36N2O2/c1-21(2,3)25-20(27)17-8-7-15-14-6-9-18-23(5,13-11-19(26)24-18)16(14)10-12-22(15,17)4/h11,13-18H,6-10,12H2,1-5H3,(H,24,26)(H,25,27)/t14-,15-,16-,17+,18+,22-,23+/m0/s1
comment: Inhibits steroid 5-alpha-reductase 2
iupac name: (1S,3aS,3bS,5aR,9aR,9bS,11aS)-N-tert-butyl-9a,11a-dimethyl-7-oxo-1,2,3,3a,3b,4,5,5a,6,9b,10,11-dodecahydroindeno[5,4-f]quinoline-1-carboxamide
xref: CHEMBL710
synonym: MK 906
synonym: MK906
synonym: MK-906
synonym: Chibro-Prosca
synonym: Finastid
synonym: Prostide
synonym: Finpecia
synonym: Proscar®
synonym: Propecia®
approved: t
ligand name: finasteride
type: SyntheticOrganicLigand

febuxostat
canonical SMILES: N#Cc1cc(ccc1OCC(C)C)c1nc(c(s1)C(=O)O)C
isomeric SMILES: N#Cc1cc(ccc1OCC(C)C)c1nc(c(s1)C(=O)O)C
in ch i key: BQSJTQLCZDPROO-UHFFFAOYSA-N
in ch i: InChI=1S/C16H16N2O3S/c1-9(2)8-21-13-5-4-11(6-12(13)7-17)15-18-10(3)14(22-15)16(19)20/h4-6,9H,8H2,1-3H3,(H,19,20)
comment: Inhibits xanthine dehydrogenase
iupac name: 2-[3-cyano-4-(2-methylpropoxy)phenyl]-4-methyl-1,3-thiazole-5-carboxylic acid
xref: CHEMBL1164729
synonym: MX-67
synonym: Tei-6720
synonym: TMX 67
synonym: Tei 6720
synonym: Adenuric®
synonym: Uloric®
approved: t
ligand name: febuxostat
type: SyntheticOrganicLigand

ezetimibe
in ch i key: OLNTVTPDXPETLC-XPWALMASSA-N
in ch i: InChI=1S/C24H21F2NO3/c25-17-5-1-15(2-6-17)22(29)14-13-21-23(16-3-11-20(28)12-4-16)27(24(21)30)19-9-7-18(26)8-10-19/h1-12,21-23,28-29H,13-14H2/t21-,22+,23-/m1/s1
comment: Inhibits the intestinal cholesterol uptake protein Niemann-Pick C1-like protein 1 (NPC1L1). Analysis of cryo-EM structures reveals how NPC1L1 transports cholesterol and the mechanism of ezetimibe inhibition <Reference id=39785/>.
iupac name: (3R,4S)-1-(4-fluorophenyl)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-(4-hydroxyphenyl)azetidin-2-one
xref: CHEMBL1138
synonym: Ezedoc
synonym: Ezetib
synonym: Ezetrol
synonym: Maxetibe
synonym: Zemitra
synonym: Zetavim
synonym: Zient
synonym: Zetia®
synonym: SCH 58235
synonym: SCH-58235
approved: t
ligand name: ezetimibe
type: SyntheticOrganicLigand

etoposide
in ch i key: VJJPUSNTGOMMGY-MRVIYFEKSA-N
in ch i: InChI=1S/C29H32O13/c1-11-36-9-20-27(40-11)24(31)25(32)29(41-20)42-26-14-7-17-16(38-10-39-17)6-13(14)21(22-15(26)8-37-28(22)33)12-4-18(34-2)23(30)19(5-12)35-3/h4-7,11,15,20-22,24-27,29-32H,8-10H2,1-3H3/t11-,15+,20-,21-,22+,24-,25-,26-,27-,29+/m1/s1
comment: A DNA topoisomerase II inhibitor which is a synthetic derivative of podophyllotoxin, found in the American Mayapple (Podophyllum peltatum).
iupac name: (5S,5aR,8aR,9R)-5-[[(2R,4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-methyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-6-yl]oxy]-9-(4-hydroxy-3,5-dimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[6,5-f][1,3]benzodioxol-8-one
xref: CHEMBL44657
synonym: Eposin
synonym: Lastet
synonym: Vepesid J
synonym: Zuyeyidal
synonym: Etopophos®
synonym: VePesid®
synonym: Toposar®
synonym: trans-etoposide
synonym: (-)-etoposide
synonym: VP-16
synonym: VP 16-213
approved: t
ligand name: etoposide
type: SyntheticOrganicLigand

ethoxzolamide
canonical SMILES: CCOc1ccc2c(c1)sc(n2)S(=O)(=O)N
isomeric SMILES: CCOc1ccc2c(c1)sc(n2)S(=O)(=O)N
in ch i key: OUZWUKMCLIBBOG-UHFFFAOYSA-N
in ch i: InChI=1S/C9H10N2O3S2/c1-2-14-6-3-4-7-8(5-6)15-9(11-7)16(10,12)13/h3-5H,2H2,1H3,(H2,10,12,13)
comment: Carbonic anhydrase inhibitor
iupac name: 6-ethoxy-1,3-benzothiazole-2-sulfonamide
xref: CHEMBL18
synonym: Cardrase®
synonym: ethoxazolamide
synonym: ethoxyzolamide
synonym: diuretic C
synonym: Ethamide®
approved: t
ligand name: ethoxzolamide
type: SyntheticOrganicLigand

azacitidine
canonical SMILES: OCC1OC(C(C1O)O)n1cnc(nc1=O)N
in ch i key: NMUSYJAQQFHJEW-KVTDHHQDSA-N
in ch i: InChI=1S/C8H12N4O5/c9-7-10-2-12(8(16)11-7)6-5(15)4(14)3(1-13)17-6/h2-6,13-15H,1H2,(H2,9,11,16)/t3-,4-,5-,6-/m1/s1
comment: DNA methyltransferase and RNA inhibitor. Azacitidine inhibits DNA methylation in vitro <Reference id=23330/>, but not by directly interacting with the methyltransferase enzyme DNMT1.
iupac name: 4-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,3,5-triazin-2-one
xref: CHEMBL1489
synonym: Onureg® (CC-486; oral azacitidine)
synonym: U-18496
synonym: ladakamycin
synonym: 5-azacytidine
synonym: 5-AZAC
synonym: Vidaza®
synonym: Onureg®
approved: t
ligand name: azacitidine
type: SyntheticOrganicLigand

allopurinol
canonical SMILES: O=c1ncnc2c1c[nH][nH]2
isomeric SMILES: O=c1ncnc2c1c[nH][nH]2
in ch i key: OFCNXPDARWKPPY-UHFFFAOYSA-N
in ch i: InChI=1S/C5H4N4O/c10-5-3-1-8-9-4(3)6-2-7-5/h1-2H,(H2,6,7,8,9,10)
comment: Marketed formulations may contain (PubChem CID 16051976).
iupac name: 1H,2H,4H-pyrazolo[3,4-d]pyrimidin-4-one
xref: CHEMBL1467
synonym: 7Hp
synonym: Adenock
synonym: Ailural
synonym: Allopuren
synonym: Allohexal
synonym: Allopur
synonym: Allozym
synonym: Allural
synonym: Aloral
synonym: Aloprim®
synonym: BW-56158
synonym: BW-56-158
synonym: Lopurin
synonym: Zyloprim®
approved: t
ligand name: allopurinol
type: SyntheticOrganicLigand

eribulin
in ch i key: UFNVPOGXISZXJD-JBQZKEIOSA-N
in ch i: InChI=1S/C40H59NO11/c1-19-11-24-5-7-28-20(2)12-26(45-28)9-10-40-17-33-36(51-40)37-38(50-33)39(52-40)35-29(49-37)8-6-25(47-35)13-22(42)14-27-31(16-30(46-24)21(19)3)48-32(34(27)44-4)15-23(43)18-41/h19,23-39,43H,2-3,5-18,41H2,1,4H3/t19-,23+,24+,25-,26+,27+,28+,29+,30-,31+,32-,33-,34-,35+,36+,37+,38-,39+,40+/m1/s1
comment: A pan tubulin inhibitor which is a fully synthetic macrocyclic ketone analogue of the marine sponge natural product halichondrin B (a mitosis inhibitor). Marketed formulations may contain eribulin mesylate (PubChem CID 17755248).
xref: CHEMBL1683590
synonym: E7389
synonym: ER 086526
synonym: NSC-707389
synonym: Halaven®
approved: t
ligand name: eribulin
type: SyntheticOrganicLigand

enzalutamide
in ch i key: WXCXUHSOUPDCQV-UHFFFAOYSA-N
comment: Enzalutamide is an androgen receptor antagonist.
iupac name: 4-{3-[4-cyano-3-(trifluoromethyl)phenyl]-5,5-dimethyl-4-oxo-2-sulfanylideneimidazolidin-1-yl}-2-fluoro-N-methylbenzamide
xref: CHEMBL1082407
synonym: MDV3100
synonym: MDV-3100
synonym: Xtandi®
approved: t
ligand name: enzalutamide
type: SyntheticOrganicLigand

enoxaparin
in ch i key: HTTJABKRGRZYRN-UHFFFAOYSA-N
comment: A Low-Molecular-Weight Heparin antithrombin-III activator. It consists of fractionated material from pig mucosa but the PubChem structure represents the major form. Biosimilar drugs: The EMA approved enoxaparin biosimilars named Inhixa and Thorinane in 2016.
iupac name: 6-[5-acetamido-4,6-dihydroxy-2-(sulfooxymethyl)oxan-3-yl]oxy-3-[5-(6-carboxy-4,5-dihydroxy-3-sulfooxyoxan-2-yl)oxy-6-(hydroxymethyl)-3-(sulfoamino)-4-sulfooxyoxan-2-yl]oxy-4-hydroxy-5-sulfooxyoxane-2-carboxylic acid
xref: CHEMBL1201476
synonym: Lovenox Hp
synonym: Lovenox®
synonym: Clexane®
synonym: RP-54563
synonym: PK-10169
synonym: Normiflo
synonym: enoxaparin sodium
approved: t
ligand name: enoxaparin
type: SyntheticOrganicLigand

dorzolamide
canonical SMILES: CCNC1CC(C)S(=O)(=O)c2c1cc(s2)S(=O)(=O)N
in ch i key: IAVUPMFITXYVAF-XPUUQOCRSA-N
in ch i: InChI=1S/C10H16N2O4S3/c1-3-12-8-4-6(2)18(13,14)10-7(8)5-9(17-10)19(11,15)16/h5-6,8,12H,3-4H2,1-2H3,(H2,11,15,16)/t6-,8-/m0/s1
comment: Marketed formulations may contain dorzolamide hydrochloride (PubChem CID 6918132).
iupac name: 4-ethylamino-6-methyl-7,7-dioxo-5,6-dihydro-4H-thieno[5,4-b]thiopyran-2-sulfonamide
xref: CHEMBL218490
synonym: Cosopt Pf
synonym: Trusopt®
approved: t
ligand name: dorzolamide
type: SyntheticOrganicLigand

docetaxel
in ch i key: ZDZOTLJHXYCWBA-VCVYQWHSSA-N
in ch i: InChI=1S/C43H53NO14/c1-22-26(55-37(51)32(48)30(24-15-11-9-12-16-24)44-38(52)58-39(3,4)5)20-43(53)35(56-36(50)25-17-13-10-14-18-25)33-41(8,34(49)31(47)29(22)40(43,6)7)27(46)19-28-42(33,21-54-28)57-23(2)45/h9-18,26-28,30-33,35,46-48,53H,19-21H2,1-8H3,(H,44,52)/t26-,27-,28+,30-,31+,32+,33-,35-,41+,42-,43+/m0/s1
comment: Docetaxel is a pan tubulin inhibitor which is a semi-synthetic analogue of paclitaxel (taxol), an extract from the bark of the rare Pacific yew tree Taxus brevifolia.
xref: CHEMBL92
synonym: docetaxel anhydrous
synonym: EmDOC
synonym: Taxotere®
synonym: Docecad®
approved: t
ligand name: docetaxel
type: SyntheticOrganicLigand

deslanoside
in ch i key: OBATZBGFDSVCJD-LALPQLPRSA-N
in ch i: InChI=1S/C47H74O19/c1-20-41(64-36-16-30(50)42(21(2)60-36)65-37-17-31(51)43(22(3)61-37)66-44-40(56)39(55)38(54)32(18-48)63-44)29(49)15-35(59-20)62-25-8-10-45(4)24(13-25)6-7-27-28(45)14-33(52)46(5)26(9-11-47(27,46)57)23-12-34(53)58-19-23/h12,20-22,24-33,35-44,48-52,54-57H,6-11,13-19H2,1-5H3/t20-,21-,22-,24-,25+,26-,27-,28+,29+,30+,31+,32-,33-,35+,36+,37+,38-,39+,40-,41-,42-,43-,44+,45+,46+,47+/m1/s1
comment: Sodium/potassium-transporting ATPase inhibitor (pan). This compound was originally discovered in the leaves of Digitalis lanata, the woolly foxglove.
iupac name: 4-[(3S,5R,8R,9S,10S,12R,13S,14S,17R)-12,14-dihydroxy-3-[(2R,4S,5S,6R)-4-hydroxy-5-[(2S,4S,5S,6R)-4-hydroxy-5-[(2S,4S,5S,6R)-4-hydroxy-6-methyl-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-6-methyloxan-2-yl]oxy-6-methyloxan-2-yl]oxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]-5H-furan-2-one
xref: CHEMBL1614
synonym: Deacetyllanatoside C
synonym: Cedilanide®
synonym: desacetyl-lanatoside C
synonym: lekozid
synonym: ceglunat
synonym: desace
approved: t
ligand name: deslanoside
type: SyntheticOrganicLigand

decitabine
canonical SMILES: OCC1OC(CC1O)n1cnc(nc1=O)N
isomeric SMILES: OC[C@H]1O[C@H](C[C@@H]1O)n1cnc(nc1=O)N
in ch i key: XAUDJQYHKZQPEU-KVQBGUIXSA-N
in ch i: InChI=1S/C8H12N4O4/c9-7-10-3-12(8(15)11-7)6-1-4(14)5(2-13)16-6/h3-6,13-14H,1-2H2,(H2,9,11,15)/t4-,5+,6+/m0/s1
comment: DNA methylation inhibitor and RNA inhibitor. Like <Ligand id=6796/>, decitabine inhibits DNA methylation in vitro <Reference id=23330/>, but not by directly interacting with methyltransferase enzymes.
iupac name: 4-amino-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,3,5-triazin-2-one
xref: CHEMBL1201129
synonym: ASTX-727
synonym: ASTX727 (decitabine + cedazuridine)
synonym: Inqovi® (decitabine + cedazuridine)
synonym: DAC
synonym: azadC
synonym: Dacogen®
synonym: dezocitidine
synonym: 5-azadeoxycytidine
approved: t
ligand name: decitabine
type: SyntheticOrganicLigand

clofarabine
canonical SMILES: OCC1OC(C(C1O)F)n1cnc2c1nc(Cl)nc2N
in ch i key: WDDPHFBMKLOVOX-AYQXTPAHSA-N
comment: A DNA polymerase (α/δ/ε) inhibitor, DNA and ribonucleoside-diphosphate reductase (RR1) inhibitor.
iupac name: (2R,3R,4S,5R)-5-(6-amino-2-chloropurin-9-yl)-4-fluoro-2-(hydroxymethyl)oxolan-3-ol
xref: CHEMBL1750
synonym: CAFdA
synonym: Clolar®
synonym: Evoltra®
synonym: clofarex
synonym: Cl-F-araA
approved: t
ligand name: clofarabine
type: SyntheticOrganicLigand

chlorpropamide
canonical SMILES: CCCNC(=O)NS(=O)(=O)c1ccc(Cl)cc1
isomeric SMILES: CCCNC(=O)NS(=O)(=O)c1ccc(Cl)cc1
in ch i key: RKWGIWYCVPQPMF-UHFFFAOYSA-N
comment: A sulfonylurea family drug inhibiting sulfonylurea receptor 1 (ABCC8)/Kir6.2 (KCNJ11)
iupac name: 1-(4-chlorobenzenesulfonyl)-3-propylurea
xref: CHEMBL498
synonym: Adiaben
synonym: Apo-Chlorpropamide
synonym: Asucrol
synonym: Catanil
synonym: Chlorodiabina
synonym: Chloronase
synonym: Chloropropamide
synonym: meldian
synonym: diabetoral
synonym: dynalase
synonym: diabinese
synonym: Diabenese®
synonym: Glucamide®
approved: t
ligand name: chlorpropamide
type: SyntheticOrganicLigand

carmustine
canonical SMILES: ClCCNC(=O)N(CCCl)N=O
isomeric SMILES: ClCCNC(=O)N(CCCl)N=O
in ch i key: DLGOEMSEDOSKAD-UHFFFAOYSA-N
in ch i: InChI=1S/C5H9Cl2N3O2/c6-1-3-8-5(11)10(9-12)4-2-7/h1-4H2,(H,8,11)
comment: A glutathione reductase inhibitor, DNA/RNA inhibitor.
iupac name: 1,3-bis(2-chloroethyl)-3-nitrosourea
xref: CHEMBL513
synonym: Becenun
synonym: Bicnu
synonym: Carmubris
synonym: Gliadel
synonym: Gliadelwafer
synonym: Nitrumon
synonym: BiCNU®
synonym: Carustine®
approved: t
ligand name: carmustine
type: SyntheticOrganicLigand

capecitabine
in ch i key: GAGWJHPBXLXJQN-UORFTKCHSA-N
in ch i: InChI=1S/C15H22FN3O6/c1-3-4-5-6-24-15(23)18-12-9(16)7-19(14(22)17-12)13-11(21)10(20)8(2)25-13/h7-8,10-11,13,20-21H,3-6H2,1-2H3,(H,17,18,22,23)/t8-,10-,11-,13-/m1/s1
comment: Capecitabine is a prodrug, that is enzymatically converted to 5-fluorouracil (active agent). It is a thymidylate synthase inhibitor.
iupac name: pentyl N-[1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-methyloxolan-2-yl]-5-fluoro-2-oxopyrimidin-4-yl]carbamate
xref: CHEMBL1773
synonym: Ro-091978000
synonym: Ro-09-1978-000
synonym: Xeloda®
approved: t
ligand name: capecitabine
type: SyntheticOrganicLigand

cabazitaxel
in ch i key: BMQGVNUXMIRLCK-OAGWZNDDSA-N
in ch i: InChI=1S/C45H57NO14/c1-24-28(57-39(51)33(48)32(26-17-13-11-14-18-26)46-40(52)60-41(3,4)5)22-45(53)37(58-38(50)27-19-15-12-16-20-27)35-43(8,36(49)34(55-10)31(24)42(45,6)7)29(54-9)21-30-44(35,23-56-30)59-25(2)47/h11-20,28-30,32-35,37,48,53H,21-23H2,1-10H3,(H,46,52)/t28-,29-,30+,32-,33+,34+,35-,37-,43+,44-,45+/m0/s1
comment: Cabazitaxel is a pan tubulin inhibitor of the taxane class of compounds.
xref: CHEMBL1201748
synonym: Jevanta®
synonym: XRP-6258
synonym: taxoid XRP6258
synonym: TXD 258
approved: t
ligand name: cabazitaxel
type: SyntheticOrganicLigand

acetyldigitoxin
in ch i key: HPMZBILYSWLILX-UMDUKNJSSA-N
in ch i: InChI=1S/C43H66O14/c1-21-38(48)33(54-24(4)44)19-37(51-21)57-40-23(3)53-36(18-32(40)46)56-39-22(2)52-35(17-31(39)45)55-27-9-12-41(5)26(16-27)7-8-30-29(41)10-13-42(6)28(11-14-43(30,42)49)25-15-34(47)50-20-25/h15,21-23,26-33,35-40,45-46,48-49H,7-14,16-20H2,1-6H3/t21-,22-,23-,26-,27+,28-,29+,30-,31+,32+,33+,35+,36+,37+,38-,39-,40-,41+,42-,43+/m1/s1
comment: Sodium/potassium-transporting ATPase inhibitor (pan)
iupac name: [(2R,3R,4S,6S)-3-hydroxy-6-[(2R,3S,4S,6S)-4-hydroxy-6-[(2R,3S,4S,6R)-4-hydroxy-6-[[(3S,5R,8R,9S,10S,13R,14S,17R)-14-hydroxy-10,13-dimethyl-17-(5-oxo-2H-furan-3-yl)-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-yl]oxy]-2-methyloxan-3-yl]oxy-2-methyloxan-3-yl]oxy-2-methyloxan-4-yl] acetate
xref: CHEMBL3545057
synonym: acetyldiginatin
synonym: alpha-acetyldigitoxin
synonym: Acigoxin
synonym: Acylanid®
approved: t
ligand name: acetyldigitoxin
type: SyntheticOrganicLigand

acetohexamide
in ch i key: VGZSUPCWNCWDAN-UHFFFAOYSA-N
in ch i: InChI=1S/C15H20N2O4S/c1-11(18)12-7-9-14(10-8-12)22(20,21)17-15(19)16-13-5-3-2-4-6-13/h7-10,13H,2-6H2,1H3,(H2,16,17,19)
comment: A sulfonylurea family drug.
iupac name: 3-(4-acetylbenzenesulfonyl)-1-cyclohexylurea
xref: CHEMBL1589
synonym: Hypoglicil
synonym: Metaglucina
synonym: Dimelin
synonym: Minoral
synonym: Ordimel
synonym: Gamadiabet
synonym: Dimelor
synonym: Dymelor®
approved: t
ligand name: acetohexamide
type: SyntheticOrganicLigand

acetazolamide
canonical SMILES: CC(=O)Nc1nnc(s1)S(=O)(=O)N
isomeric SMILES: CC(=O)Nc1nnc(s1)S(=O)(=O)N
in ch i key: BZKPWHYZMXOIDC-UHFFFAOYSA-N
in ch i: InChI=1S/C4H6N4O3S2/c1-2(9)6-3-7-8-4(12-3)13(5,10)11/h1H3,(H2,5,10,11)(H,6,7,9)
comment: Carbonic anhydrase inhibitor
iupac name: N-(5-sulfamoyl-1,3,4-thiadiazol-2-yl)acetamide
xref: CHEMBL20
synonym: Atenezol
synonym: Apo-Acetazolamide
synonym: Acetazolamide Sodium
synonym: Diacarb
synonym: Defiltran
synonym: Acetamox
synonym: Dehydratin
synonym: Dazamide
synonym: Cidamex
synonym: Glaupax
synonym: Edemox
synonym: Diluran
synonym: Diamox®
approved: t
ligand name: acetazolamide
type: SyntheticOrganicLigand

acarbose
in ch i key: XUFXOAAUWZOOIT-SXARVLRPSA-N
comment: Maltase-glucoamylase and pancreatic amylase inhibitor. Many isomeric alternative structures for this compound are available: to go to the PubChem listing click here. It is not clear which isomer is an exact match to the structure given in the INN record for this compound.
iupac name: (2R,3R,4R,5S,6R)-5-[(2R,3R,4R,5S,6R)-5-[(2R,3R,4S,5S,6R)-3,4-dihydroxy-6-methyl-5-[[(1S,4R,5S,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)-1-cyclohex-2-enyl]amino]oxan-2-yl]oxy-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-(hydroxymethyl)oxane-2,3,4-triol
xref: CHEMBL1566
synonym: BAY-G 5421
synonym: BAY-G-5421
synonym: Prandase
synonym: Precose®
synonym: Glucobay®
approved: t
ligand name: acarbose
type: SyntheticOrganicLigand

compound 6 [PMID: 22533316]
canonical SMILES: CCCN(CCCC#CC1CCC(CC1)N(C(=O)Oc1ccc(cc1)Cl)C)C
in ch i key: FXHALLFKKHHPNQ-XUTJKUGGSA-N
in ch i: InChI=1S/C23H33ClN2O2/c1-4-17-25(2)18-7-5-6-8-19-9-13-21(14-10-19)26(3)23(27)28-22-15-11-20(24)12-16-22/h11-12,15-16,19,21H,4-5,7,9-10,13-14,17-18H2,1-3H3/t19-,21-
comment: The structure of this compound was drawn as represented in the listed reference. CID 60154274 shows a non-chiral representation of the compound.
iupac name: 4-chlorophenyl N-methyl-N-[(1r,4r)-4-{5-[methyl(propyl)amino]pent-1-yn-1-yl}cyclohexyl]carbamate
xref: CHEMBL2219823
approved: f
ligand name: compound 6 [PMID: 22533316]
type: SyntheticOrganicLigand

vincristine
in ch i key: OGWKCGZFUXNPDA-XQKSVPLYSA-N
in ch i: InChI=1S/C46H56N4O10/c1-7-42(55)22-28-23-45(40(53)58-5,36-30(14-18-48(24-28)25-42)29-12-9-10-13-33(29)47-36)32-20-31-34(21-35(32)57-4)50(26-51)38-44(31)16-19-49-17-11-15-43(8-2,37(44)49)39(60-27(3)52)46(38,56)41(54)59-6/h9-13,15,20-21,26,28,37-39,47,55-56H,7-8,14,16-19,22-25H2,1-6H3/t28-,37+,38-,39-,42+,43-,44-,45+,46+/m1/s1
comment: A pan tubulin inhibitor, isolated from Catharanthus roseus (the Madagascar periwinkle, formerly Vinca rosea). Marketed formulations contain vincristine sulfate (PubChem CID 249332).
xref: CHEMBL90555
synonym: NSC-67574
synonym: kyocristine
synonym: leurocristine sulfate
synonym: 22-oxovincaleukoblastine
synonym: Vincrex
synonym: Vincasar
synonym: Marqibo
synonym: Vincasar Pfs
synonym: Vincristine Sulfate Pfs
synonym: Oncovin®
approved: t
ligand name: vincristine
type: NaturalProductLigand

tacrolimus
in ch i key: QJJXYPPXXYFBGM-LFZNUXCKSA-N
in ch i: InChI=1S/C44H69NO12/c1-10-13-31-19-25(2)18-26(3)20-37(54-8)40-38(55-9)22-28(5)44(52,57-40)41(49)42(50)45-17-12-11-14-32(45)43(51)56-39(29(6)34(47)24-35(31)48)27(4)21-30-15-16-33(46)36(23-30)53-7/h10,19,21,26,28-34,36-40,46-47,52H,1,11-18,20,22-24H2,2-9H3/b25-19+,27-21+/t26-,28+,29+,30-,31+,32-,33+,34-,36+,37-,38-,39+,40+,44+/m0/s1
comment: Tacrolimus acts as a calcineurin inhibitor and has immunosuppressive effects.
xref: CHEMBL269732
synonym: FK506
synonym: Hecoria
synonym: Advagraf
synonym: fujimycin
synonym: Protopic®
synonym: Prograf®
synonym: Modigraf
approved: t
ligand name: tacrolimus
type: SyntheticOrganicLigand

pimecrolimus
in ch i key: KASDHRXLYQOAKZ-XDSKOBMDSA-N
in ch i: InChI=1S/C43H68ClNO11/c1-10-30-18-24(2)17-25(3)19-36(53-8)39-37(54-9)21-27(5)43(51,56-39)40(48)41(49)45-16-12-11-13-32(45)42(50)55-38(28(6)33(46)23-34(30)47)26(4)20-29-14-15-31(44)35(22-29)52-7/h18,20,25,27-33,35-39,46,51H,10-17,19,21-23H2,1-9H3/b24-18+,26-20+/t25-,27+,28+,29-,30+,31-,32-,33-,35+,36-,37-,38+,39+,43+/m0/s1
comment: Inhibits FK506-binding protein 1A
xref: CHEMBL1200686
synonym: Elidel®
synonym: SDZ-ASM 981
synonym: SDZ ASM 981
approved: t
ligand name: pimecrolimus
type: SyntheticOrganicLigand

digitoxin
in ch i key: WDJUZGPOPHTGOT-XUDUSOBPSA-N
in ch i: InChI=1S/C41H64O13/c1-20-36(46)29(42)16-34(49-20)53-38-22(3)51-35(18-31(38)44)54-37-21(2)50-33(17-30(37)43)52-25-8-11-39(4)24(15-25)6-7-28-27(39)9-12-40(5)26(10-13-41(28,40)47)23-14-32(45)48-19-23/h14,20-22,24-31,33-38,42-44,46-47H,6-13,15-19H2,1-5H3/t20-,21-,22-,24-,25+,26-,27+,28-,29+,30+,31+,33+,34+,35+,36-,37-,38-,39+,40-,41+/m1/s1
comment: Sodium/potassium-transporting ATPase inhibitor (pan)
iupac name: 4-[(3S,5R,8R,9S,10S,13R,14S,17R)-3-[(2R,4S,5S,6R)-5-[(2S,4S,5S,6R)-5-[(2S,4S,5S,6R)-4,5-dihydroxy-6-methyloxan-2-yl]oxy-4-hydroxy-6-methyloxan-2-yl]oxy-4-hydroxy-6-methyloxan-2-yl]oxy-14-hydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]-5H-furan-2-one
xref: CHEMBL254219
synonym: Digitoksin
synonym: Tardigal
synonym: digitoxoside
synonym: unidigin
synonym: Crystodigin
approved: t
ligand name: digitoxin
type: SyntheticOrganicLigand

palmitoyl-CoA
in ch i key: MNBKLUUYKPBKDU-BBECNAHFSA-N
iupac name: S-[2-[3-[[(2R)-4-[[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-phosphonooxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl]oxy-2-hydroxy-3,3-dimethylbutanoyl]amino]propanoylamino]ethyl] hexadecanethioate
synonym: palmitoyl coenzyme A
approved: f
ligand name: palmitoyl-CoA
type: MetaboliteLigand

CCG-100602
in ch i key: MOQCFMZWVKQBAP-UHFFFAOYSA-N
comment: Analogoue of CGC-1423 with improved selectivity for inhibition of RhoA/C-mediated gene transcription and attenuated cytotoxicity
iupac name: [3,5-bis(trifluoromethyl)benzoyl]-N-(4-chlorophenyl)piperidine-3-carboxamide
xref: CHEMBL603141
synonym: CCG100602
synonym: CCG 100602
synonym: compound 4g [PMID: 19963382]
approved: f
ligand name: CCG-100602
type: SyntheticOrganicLigand

CCG-203971
in ch i key: HERLZBNILRVHQN-UHFFFAOYSA-N
in ch i: InChI=1S/C23H21ClN2O3/c24-19-8-10-20(11-9-19)25-22(27)18-6-2-12-26(15-18)23(28)17-5-1-4-16(14-17)21-7-3-13-29-21/h1,3-5,7-11,13-14,18H,2,6,12,15H2,(H,25,27)
comment: Novel inhibitor of Rho/MKL1/SRF-mediated gene transcription that inhibits invasion of PC-3 prostate cancer cells in a Matrigel model of metastasis (a CCG-1423 analogue)
iupac name: N-(4-chlorophenyl)-1-[3-(furan-2-yl)benzoyl]piperidine-3-carboxamide
xref: CHEMBL2398678
synonym: CCG203971
synonym: CCG 203971
synonym: compound 8a [PMID: 23707258]
approved: f
ligand name: CCG-203971
type: SyntheticOrganicLigand

CCG-977
in ch i key: VBZKJHSBGYDJAN-UHFFFAOYSA-N
comment: CCG-977 is an analogue of CCG 1423, both of which inhibit RhoA transcriptional signaling via an unkown mechanism of action. Both are tool compounds for disrupting the transcriptional responses of the Rho pathway in cancer.
synonym: CCG977
synonym: CCG 977
approved: f
ligand name: CCG-977
type: SyntheticOrganicLigand

CCG-1423
in ch i key: DSMXVSGJIDFLKP-UHFFFAOYSA-N
comment: CCG-1423 inhibits RhoA transcriptional signaling via an unknown mechanism of action but is tool compound for the disruption of transcriptional responses of the Rho pathway in cancer.
iupac name: N-[1-[(4-chlorophenyl)amino]-1-oxopropan-2-yl]oxy-3,5-bis(trifluoromethyl)benzamide
synonym: CCG1423
synonym: CCG 1423
approved: f
ligand name: CCG-1423
type: SyntheticOrganicLigand

abiraterone
in ch i key: GZOSMCIZMLWJML-VJLLXTKPSA-N
in ch i: InChI=1S/C24H31NO/c1-23-11-9-18(26)14-17(23)5-6-19-21-8-7-20(16-4-3-13-25-15-16)24(21,2)12-10-22(19)23/h3-5,7,13,15,18-19,21-22,26H,6,8-12,14H2,1-2H3/t18-,19-,21-,22-,23-,24+/m0/s1
comment: Abiraterone is the active from of the abiraterone acetate prodrug.
iupac name: (3S,8R,9S,10R,13S,14S)-10,13-dimethyl-17-pyridin-3-yl-2,3,4,7,8,9,11,12,14,15-decahydro-1H-cyclopenta[a]phenanthren-3-ol
xref: CHEMBL254328
approved: f
ligand name: abiraterone
type: SyntheticOrganicLigand

MRL24
in ch i key: OFCWBJAYEIROGZ-KRWDZBQOSA-N
in ch i: InChI=1S/C28H24F3NO6/c1-16-23(14-18-5-4-6-21(13-18)37-17(2)27(34)35)24-15-22(38-28(29,30)31)11-12-25(24)32(16)26(33)19-7-9-20(36-3)10-8-19/h4-13,15,17H,14H2,1-3H3,(H,34,35)/t17-/m0/s1
comment: This is compound 24 in <Reference id=23103/>
iupac name: (2S)-2-[3-[[1-(4-methoxybenzoyl)-2-methyl-5-(trifluoromethoxy)indol-3- yl]methyl]phenoxy]propanoic acid
xref: CHEMBL179330
synonym: MRL 24
approved: f
ligand name: MRL24
type: SyntheticOrganicLigand

MRL20
in ch i key: BWTOBMCYVACNJZ-KRWDZBQOSA-N
in ch i: InChI=1S/C28H24F3NO6/c1-16-22(14-19-6-4-5-7-25(19)37-17(2)27(34)35)23-15-21(38-28(29,30)31)12-13-24(23)32(16)26(33)18-8-10-20(36-3)11-9-18/h4-13,15,17H,14H2,1-3H3,(H,34,35)/t17-/m0/s1
comment: This is compound 20 in <Reference id=23103/>
iupac name: (2S)-2-[2-[[1-(4-methoxybenzoyl)-2-methyl-5-(trifluoromethoxy)indol-3-yl]methyl]phenoxy]propanoic acid
xref: CHEMBL181937
approved: f
ligand name: MRL20
type: SyntheticOrganicLigand

idelalisib
in ch i key: IFSDAJWBUCMOAH-HNNXBMFYSA-N
in ch i: InChI=1S/C22H18FN7O/c1-2-15(28-20-18-19(25-11-24-18)26-12-27-20)21-29-16-10-6-9-14(23)17(16)22(31)30(21)13-7-4-3-5-8-13/h3-12,15H,2H2,1H3,(H2,24,25,26,27,28)/t15-/m0/s1
comment: Idelalisib is highly selective and potent oral inhibitor of phosphoinositide 3-kinase (PI3K) δ.
iupac name: 5-fluoro-3-phenyl-2-[(1S)-1-(7H-purin-6-ylamino)propyl]quinazolin-4-one
xref: CHEMBL2216870
synonym: CAL-101/CAL101
synonym: GS-1101
synonym: Zydelig®
approved: t
ligand name: idelalisib
type: SyntheticOrganicLigand

GSK2606414
in ch i key: PXVQGBJMIQCDEX-UHFFFAOYSA-N
in ch i: InChI=1S/C24H19F4N5O/c1-32-11-18(21-22(29)30-12-31-23(21)32)14-2-3-19-15(9-14)4-5-33(19)20(34)8-13-6-16(24(26,27)28)10-17(25)7-13/h2-3,6-7,9-12H,4-5,8H2,1H3,(H2,29,30,31)
comment: GSK2606414 is an analogue identified by a medicinal chemistry study to find novel, potent and selective protein kinase R (PKR)-like endoplasmic reticulum kinase (PERK) inhibitors <Reference id=23100/>. The official HGNC endorsed name for PERK is eukaryotic translation initiation factor 2-alpha kinase 3 (with gene symbol EIF2AK3). GSK2606414 is highly selective and is orally available.
iupac name: 1-[5-(4-amino-7-methylpyrrolo[2,3-d]pyrimidin-5-yl)-2, 3-dihydroindol-1-yl]-2-[3-fluoro-5-(trifluoromethyl)phenyl]ethanone
xref: CHEMBL2171125
synonym: GSK PERK Inhibitor
synonym: 3-fluoro-GSK2606414
synonym: compound 38 [PMID: 22827572]
approved: f
ligand name: GSK2606414
type: SyntheticOrganicLigand

LSP1-2111
canonical SMILES: COc1cc(cc(c1O)[N+](=O)[O-])C(P(=O)(CCC(C(=O)O)N)O)O
isomeric SMILES: COc1cc(cc(c1O)[N+](=O)[O-])C(P(=O)(CC[C@@H](C(=O)O)N)O)O
in ch i key: PEXVMHLARUAHNC-KAJCPDDVSA-N
in ch i: InChI=1S/C12H17N2O9P/c1-23-9-5-6(4-8(10(9)15)14(19)20)12(18)24(21,22)3-2-7(13)11(16)17/h4-5,7,12,15,18H,2-3,13H2,1H3,(H,16,17)(H,21,22)/t7-,12?/m0/s1
iupac name: (2S)-2-amino-4-{hydroxy[hydroxy(4-hydroxy-3-methoxy-5-nitrophenyl)methyl]phosphoryl}butanoic acid
xref: CHEMBL3114672
approved: f
ligand name: LSP1-2111
type: SyntheticOrganicLigand

dihydrolipoic acid
canonical SMILES: SCCC(CCCCC(=O)O)S
isomeric SMILES: SCCC(CCCCC(=O)O)S
in ch i key: IZFHEQBZOYJLPK-UHFFFAOYSA-N
in ch i: InChI=1S/C8H16O2S2/c9-8(10)4-2-1-3-7(12)5-6-11/h7,11-12H,1-6H2,(H,9,10)
iupac name: 6,8-bis-sulfanyloctanoic acid
approved: f
ligand name: dihydrolipoic acid
type: SyntheticOrganicLigand

glutathione
canonical SMILES: SCC(C(=O)NCC(=O)O)NC(=O)CCC(C(=O)O)N
in ch i key: RWSXRVCMGQZWBV-WDSKDSINSA-N
in ch i: InChI=1S/C10H17N3O6S/c11-5(10(18)19)1-2-7(14)13-6(4-20)9(17)12-3-8(15)16/h5-6,20H,1-4,11H2,(H,12,17)(H,13,14)(H,15,16)(H,18,19)/t5-,6-/m0/s1
comment: Tripeptide compound
iupac name: (2S)-2-amino-5-[[(2R)-1-(carboxymethylamino)-1-oxo-3-sulfanylpropan-2-yl]amino]-5-oxopentanoic acid
xref: CHEMBL1543
synonym: GSH
approved: f
ligand name: glutathione
type: PeptideLigand

HTS01037
canonical SMILES: COC(=O)c1sc(cc1NC(=O)C=CC(=O)O)c1cccs1
isomeric SMILES: COC(=O)c1sc(cc1NC(=O)/C=C/C(=O)O)c1cccs1
in ch i key: GJODSFZNKNHKML-SNAWJCMRSA-N
in ch i: InChI=1S/C14H11NO5S2/c1-20-14(19)13-8(15-11(16)4-5-12(17)18)7-10(22-13)9-3-2-6-21-9/h2-7H,1H3,(H,15,16)(H,17,18)/b5-4+
comment: HTS01037 is an inhibitor of fatty acid binding proteins (FABPs), which acts as an antagonist of protein-protein interactions mediated by FABPs, in particular adipocyte FABP <Reference id=22694/>. The compound is a useful tool for delineating a FABP function in lipid metabolism in fat cells and inflammation in macrophages.
iupac name: (E)-4-[(2-methoxycarbonyl-5-thiophen-2-ylthiophen-3-yl)amino]-4-oxobut-2-enoic acid
xref: CHEMBL1077990
synonym: compound 1 [PMID: 19754198]
synonym: HTS 01037
approved: f
ligand name: HTS01037
type: SyntheticOrganicLigand

BMS309403
in ch i key: SJRVJRYZAQYCEE-UHFFFAOYSA-N
in ch i: InChI=1S/C31H26N2O3/c1-2-27-30(22-12-5-3-6-13-22)31(23-14-7-4-8-15-23)32-33(27)28-19-10-9-18-26(28)24-16-11-17-25(20-24)36-21-29(34)35/h3-20H,2,21H2,1H3,(H,34,35)
iupac name: 2-[3-[2-[5-ethyl-3,4-di(phenyl)pyrazol-1-yl]phenyl]phenoxy]acetic acid
xref: CHEMBL247920
synonym: BMS 309403
synonym: BMS-309403
approved: f
ligand name: BMS309403
type: SyntheticOrganicLigand

compound 26c [PMID: 16242323]
in ch i key: ZFNNBIMQDHBELV-UHFFFAOYSA-N
in ch i: InChI=1S/C40H53N5O3.2ClH/c1-6-7-21-45-38-32(19-12-20-42-38)35(29-17-11-18-31(23-29)48-22-13-16-28-14-9-8-10-15-28)37(39(45)46)44-40(47)43-36-33(26(2)3)24-30(41)25-34(36)27(4)5;;/h11-12,17-20,23-28H,6-10,13-16,21-22,41H2,1-5H3,(H2,43,44,47);2*1H
iupac name: 1-[4-amino-2,6-bis(propan-2-yl)phenyl]-3-{1-butyl-4-[3-(3-cyclohexylpropoxy)phenyl]-2-oxo-1,2-dihydro-1,8-naphthyridin-3-yl}urea dihydrochloride
approved: f
ligand name: compound 26c [PMID: 16242323]
type: SyntheticOrganicLigand

normetanephrine
canonical SMILES: NCC(c1ccc(c(c1)OC)O)O
isomeric SMILES: NCC(c1ccc(c(c1)OC)O)O
in ch i key: YNYAYWLBAHXHLL-UHFFFAOYSA-N
in ch i: InChI=1S/C9H13NO3/c1-13-9-4-6(8(12)5-10)2-3-7(9)11/h2-4,8,11-12H,5,10H2,1H3
iupac name: 4-(2-Amino-1-hydroxyethyl)-2-methoxyphenol
xref: CHEMBL774
approved: f
ligand name: normetanephrine
type: MetaboliteLigand

compound 26b [PMID: 16242323]
in ch i key: YRTFLDFDKPFNCJ-UHFFFAOYSA-N
in ch i: InChI=1S/C38H50N6O3.2ClH/c1-6-7-20-44-36-30(15-11-16-40-36)33(27-13-10-14-29(22-27)47-21-12-19-43-17-8-9-18-43)35(37(44)45)42-38(46)41-34-31(25(2)3)23-28(39)24-32(34)26(4)5;;/h10-11,13-16,22-26H,6-9,12,17-21,39H2,1-5H3,(H2,41,42,46);2*1H
iupac name: 1-[4-amino-2,6-bis(propan-2-yl)phenyl]-3-(1-butyl-2-oxo-4-{3-[3-(pyrrolidin-1-yl)propoxy]phenyl}-1,2-dihydro-1,8-naphthyridin-3-yl)urea dihydrochloride
xref: CHEMBL537859
approved: f
ligand name: compound 26b [PMID: 16242323]
type: SyntheticOrganicLigand

compound 26a [PMID: 16242323]
in ch i key: PRCCYAKPEIWHCQ-UHFFFAOYSA-N
in ch i: InChI=1S/C37H49N5O3/c1-8-9-18-42-35-29(16-11-17-39-35)32(26-14-10-15-28(20-26)45-19-12-13-23(2)3)34(36(42)43)41-37(44)40-33-30(24(4)5)21-27(38)22-31(33)25(6)7/h10-11,14-17,20-25H,8-9,12-13,18-19,38H2,1-7H3,(H2,40,41,44)
comment: Note that in <Reference id=23092/> this compound is used as its dihydrochloride salt.
iupac name: 1-[4-amino-2,6-di(propan-2-yl)phenyl]-3-[1-butyl-4-[3-(4-methylpentoxy)phenyl]-2-oxo-1,8-naphthyridin-3-yl]urea
approved: f
ligand name: compound 26a [PMID: 16242323]
type: SyntheticOrganicLigand

compound 22d [PMID: 16242323]
in ch i key: MXPCZHSTOIKVST-UHFFFAOYSA-N
in ch i: InChI=1S/C33H41N5O4.ClH/c1-6-7-16-38-31-25(12-9-15-35-31)28(22-10-8-11-23(19-22)42-18-17-39)30(32(38)40)37-33(41)36-29-24(20(2)3)13-14-26(34)27(29)21(4)5;/h8-15,19-21,39H,6-7,16-18,34H2,1-5H3,(H2,36,37,41);1H
iupac name: 1-[3-amino-2,6-bis(propan-2-yl)phenyl]-3-{1-butyl-4-[3-(2-hydroxyethoxy)phenyl]-2-oxo-1,2-dihydro-1,8-naphthyridin-3-yl}urea hydrochloride
approved: f
ligand name: compound 22d [PMID: 16242323]
type: SyntheticOrganicLigand

compound 22c [PMID: 16242323]
in ch i key: OXTVBHDILDPYAS-UHFFFAOYSA-N
in ch i: InChI=1S/C35H45N5O4.ClH/c1-6-7-15-40-33-27(13-9-14-37-33)30(25-11-8-12-26(20-25)44-17-10-16-41)32(34(40)42)39-35(43)38-31-28(22(2)3)18-24(21-36)19-29(31)23(4)5;/h8-9,11-14,18-20,22-23,41H,6-7,10,15-17,21,36H2,1-5H3,(H2,38,39,43);1H
iupac name: 1-[4-(aminomethyl)-2,6-bis(propan-2-yl)phenyl]-3-{1-butyl-4-[3-(3-hydroxypropoxy)phenyl]-2-oxo-1,2-dihydro-1,8-naphthyridin-3-yl}urea hydrochloride
approved: f
ligand name: compound 22c [PMID: 16242323]
type: SyntheticOrganicLigand

SMP-797
in ch i key: HNRUUMLUBDTZHX-UHFFFAOYSA-N
in ch i: InChI=1S/C34H43N5O4/c1-6-7-15-39-32-26(13-9-14-36-32)29(23-11-8-12-25(18-23)43-17-10-16-40)31(33(39)41)38-34(42)37-30-27(21(2)3)19-24(35)20-28(30)22(4)5/h8-9,11-14,18-22,40H,6-7,10,15-17,35H2,1-5H3,(H2,37,38,42)
iupac name: 1-[4-amino-2,6-bis(propan-2-yl)phenyl]-3-{1-butyl-4-[3-(3-hydroxypropoxy)phenyl]-2-oxo-1,2-dihydro-1,8-naphthyridin-3-yl}urea
xref: CHEMBL573970
synonym: compound 22b [PMID: 16242323]
approved: f
ligand name: SMP-797
type: SyntheticOrganicLigand

compound 18b [PMID: 16242323]
in ch i key: YCGQPIRMLGEWMW-UHFFFAOYSA-N
in ch i: InChI=1S/C35H45N5O3.ClH/c1-9-10-17-40-33-27(15-12-16-36-33)30(25-13-11-14-26(20-25)43-8)32(34(40)41)38-35(42)37-31-28(22(2)3)18-24(21-39(6)7)19-29(31)23(4)5;/h11-16,18-20,22-23H,9-10,17,21H2,1-8H3,(H2,37,38,42);1H
iupac name: 3-[1-butyl-4-(3-methoxyphenyl)-2-oxo-1,2-dihydro-1,8-naphthyridin-3-yl]-1-{4-[(dimethylamino)methyl]-2,6-bis(propan-2-yl)phenyl}urea hydrochloride
approved: f
ligand name: compound 18b [PMID: 16242323]
type: SyntheticOrganicLigand

compound 18a [PMID: 16242323]
in ch i key: SZCBDIVMCGFVPW-UHFFFAOYSA-N
in ch i: InChI=1S/C33H41N5O3.ClH/c1-7-8-15-38-31-25(13-10-14-35-31)28(23-11-9-12-24(18-23)41-6)30(32(38)39)37-33(40)36-29-26(20(2)3)16-22(19-34)17-27(29)21(4)5;/h9-14,16-18,20-21H,7-8,15,19,34H2,1-6H3,(H2,36,37,40);1H
iupac name: 1-[4-(aminomethyl)-2,6-bis(propan-2-yl)phenyl]-3-[1-butyl-4-(3-methoxyphenyl)-2-oxo-1,2-dihydro-1,8-naphthyridin-3-yl]urea hydrochloride
xref: CHEMBL558774
approved: f
ligand name: compound 18a [PMID: 16242323]
type: SyntheticOrganicLigand

compound 16 [PMID: 16242323]
in ch i key: UXCQVIIRKWYPHK-UHFFFAOYSA-N
in ch i: InChI=1S/C31H39N5O3.ClH/c1-7-8-17-36-29-24(13-10-15-33-29)25(21-11-9-12-22(18-21)39-6)28(30(36)37)35-31(38)34-27-23(19(2)3)14-16-32-26(27)20(4)5;/h9-16,18-20,26,32H,7-8,17H2,1-6H3,(H2,34,35,38);1H
iupac name: 1-[2,4-bis(propan-2-yl)-1,2-dihydropyridin-3-yl]-3-[1-butyl-4-(3-methoxyphenyl)-2-oxo-1,2-dihydro-1,8-naphthyridin-3-yl]urea hydrochloride
approved: f
ligand name: compound 16 [PMID: 16242323]
type: SyntheticOrganicLigand

compound 15b [PMID: 16242323]
in ch i key: NPAVKCDQHSYXFT-UHFFFAOYSA-N
in ch i: InChI=1S/C32H39N5O3.ClH/c1-7-8-15-37-30-24(13-10-14-34-30)27(21-11-9-12-23(16-21)40-6)29(31(37)38)36-32(39)35-28-25(19(2)3)17-22(33)18-26(28)20(4)5;/h9-14,16-20H,7-8,15,33H2,1-6H3,(H2,35,36,39);1H
iupac name: 1-[4-amino-2,6-bis(propan-2-yl)phenyl]-3-[1-butyl-4-(3-methoxyphenyl)-2-oxo-1,2-dihydro-1,8-naphthyridin-3-yl]urea hydrochloride
xref: CHEMBL541893
approved: f
ligand name: compound 15b [PMID: 16242323]
type: SyntheticOrganicLigand

compound 15a [PMID: 16242323]
in ch i key: HALGUFCFUQNPBN-UHFFFAOYSA-N
in ch i: InChI=1S/C32H39N5O3.ClH/c1-7-8-17-37-30-24(13-10-16-34-30)27(21-11-9-12-22(18-21)40-6)29(31(37)38)36-32(39)35-28-23(19(2)3)14-15-25(33)26(28)20(4)5;/h9-16,18-20H,7-8,17,33H2,1-6H3,(H2,35,36,39);1H
iupac name: 1-[3-amino-2,6-bis(propan-2-yl)phenyl]-3-[1-butyl-4-(3-methoxyphenyl)-2-oxo-1,2-dihydro-1,8-naphthyridin-3-yl]urea hydrochloride
xref: CHEMBL556797
approved: f
ligand name: compound 15a [PMID: 16242323]
type: SyntheticOrganicLigand

SM-32504
in ch i key: ORFMGXFFDRWECM-UHFFFAOYSA-N
in ch i: InChI=1S/C32H38N4O3/c1-7-8-18-36-30-26(16-11-17-33-30)27(22-12-9-13-23(19-22)39-6)29(31(36)37)35-32(38)34-28-24(20(2)3)14-10-15-25(28)21(4)5/h9-17,19-21H,7-8,18H2,1-6H3,(H2,34,35,38)
iupac name: 1-[2,6-bis(propan-2-yl)phenyl]-3-[1-butyl-4-(3-methoxyphenyl)-2-oxo-1,2-dihydro-1,8-naphthyridin-3-yl]urea
xref: CHEMBL382183
approved: f
ligand name: SM-32504
type: SyntheticOrganicLigand

compound 1 [Gotteland et al., 1997]
canonical SMILES: CCN(Cc1cccc(c1)OCc1scc(c1)c1cscc1)CC#Cc1ccccc1
isomeric SMILES: CCN(Cc1cccc(c1)OCc1scc(c1)c1cscc1)CC#Cc1ccccc1
in ch i key: GZVZWBOHPHLQFU-UHFFFAOYSA-N
in ch i: InChI=1S/C27H25NOS2/c1-2-28(14-7-11-22-8-4-3-5-9-22)18-23-10-6-12-26(16-23)29-19-27-17-25(21-31-27)24-13-15-30-20-24/h3-6,8-10,12-13,15-17,20-21H,2,14,18-19H2,1H3
iupac name: ethyl(3-phenylprop-2-yn-1-yl)[(3-{[4-(thiophen-3-yl)thiophen-2-yl]methoxy}phenyl)methyl]amine
xref: CHEMBL16178
approved: f
ligand name: compound 1 [Gotteland et al., 1997]
type: SyntheticOrganicLigand

3-methoxytyramine
canonical SMILES: NCCc1ccc(c(c1)OC)O
isomeric SMILES: NCCc1ccc(c(c1)OC)O
in ch i key: DIVQKHQLANKJQO-UHFFFAOYSA-N
in ch i: InChI=1S/C9H13NO2/c1-12-9-6-7(4-5-10)2-3-8(9)11/h2-3,6,11H,4-5,10H2,1H3
iupac name: 4-(2-aminoethyl)-2-methoxyphenol
xref: CHEMBL1160785
synonym: 3-methoxy-4-hydroxyphenethylamine
approved: f
ligand name: 3-methoxytyramine
type: MetaboliteLigand

compound 4 [PMID: 9003518]
isomeric SMILES: C/C(=C/CCC=C(CC/C=C(/CCC1OC1(C)C)/C)C)/CCCSCCC=C(C)C
in ch i key: SFOVLQYHQCMFTD-VLUDVKJZSA-N
in ch i: InChI=1S/C28H48OS/c1-23(2)13-11-21-30-22-12-18-25(4)15-9-8-14-24(3)16-10-17-26(5)19-20-27-28(6,7)29-27/h13-15,17,27H,8-12,16,18-22H2,1-7H3/b24-14?,25-15+,26-17+
iupac name: 2,2-dimethyl-3-[(3E,11E)-3,7,12-trimethyl-15-[(4-methylpent-3-en-1-yl)sulfanyl]pentadeca-3,7,11-trien-1-yl]oxirane
approved: f
ligand name: compound 4 [PMID: 9003518]
type: SyntheticOrganicLigand

compound 3 [PMID: 9003518]
isomeric SMILES: CC(CCC=C(C)C)SCC/C(=C/CC/C=C(/CC/C=C(/CCC1OC1(C)C)/C)/C)/C
in ch i key: CRZHANPLXOIADK-YNWRIEOZSA-N
in ch i: InChI=1S/C29H50OS/c1-23(2)13-11-18-27(6)31-22-21-26(5)15-10-9-14-24(3)16-12-17-25(4)19-20-28-29(7,8)30-28/h13-15,17,27-28H,9-12,16,18-22H2,1-8H3/b24-14+,25-17+,26-15+
iupac name: 2,2-dimethyl-3-[(3E,7E,11E)-3,7,12-trimethyl-14-(6-methylhept-5-en-2-ylsulfanyl)tetradeca-3,7,11-trienyl]oxirane
xref: CHEMBL64905
approved: f
ligand name: compound 3 [PMID: 9003518]
type: SyntheticOrganicLigand

29-methylidene-2,3-oxidosqualene
isomeric SMILES: C/C=C/CC/C(=C/CC/C(=C/CC/C=C(/CC/C=C(/CCC1OC1(C)C)/C)/C)/C)/CC=C
in ch i key: DOTTUEYUTNVWMJ-KSTFQPQISA-N
in ch i: InChI=1S/C31H50O/c1-8-10-11-22-29(16-9-2)23-15-21-27(4)18-13-12-17-26(3)19-14-20-28(5)24-25-30-31(6,7)32-30/h8-10,17-18,20,23,30H,2,11-16,19,21-22,24-25H2,1,3-7H3/b10-8-,26-17+,27-18+,28-20+,29-23-
iupac name: 2,2-dimethyl-3-[(3E,7E,11E,15E,19Z)-3,7,12-trimethyl-16-prop-2-enylhenicosa-3,7,11,15,19-pentaenyl]oxirane
approved: f
ligand name: 29-methylidene-2,3-oxidosqualene
type: SyntheticOrganicLigand

compound 9 [PMID: 22533316]
in ch i key: YPKPOCIBCOOAFB-KESTWPANSA-N
comment: The structure of this compound was taken from the article which describes its discovery <Reference id=23084/>. PubChem CID 71456888 shows the non-chiral molecule.
xref: CHEMBL2219825
approved: f
ligand name: compound 9 [PMID: 22533316]
type: SyntheticOrganicLigand

compound 10 [PMID: 22533316]
in ch i key: PAHWPIPXJDOVHD-QAQDUYKDSA-N
in ch i: InChI=1S/C22H31ClN2O4/c1-24(22(28)29-20-8-6-18(23)7-9-20)13-10-16-2-4-17(5-3-16)21(27)25-14-11-19(26)12-15-25/h6-9,16-17,19,26H,2-5,10-15H2,1H3/t16-,17-
comment: The structure of this compound was taken from the article which describes its discovery <Reference id=23084/>. PubChem CID 11475734 shows the non-chiral molecule.
iupac name: 4-chlorophenyl N-methyl-N-{2-[(1r,4r)-4-[(4-hydroxypiperidin-1-yl)carbonyl]cyclohexyl]ethyl}carbamate
xref: CHEMBL2164238
approved: f
ligand name: compound 10 [PMID: 22533316]
type: SyntheticOrganicLigand

compound 8 [PMID: 22533316]
in ch i key: QTPDFYJYCCDNKD-XUTJKUGGSA-N
in ch i: InChI=1S/C24H35F3N2O2/c1-4-17-28(2)18-7-5-6-8-19-9-13-21(14-10-19)29(3)23(30)31-22-15-11-20(12-16-22)24(25,26)27/h4,11-12,15-16,19,21H,1,5-10,13-14,17-18H2,2-3H3/t19-,21-
comment: The structure of this compound was taken from the article which describes its discovery <Reference id=23084/>. PubChem CID 10138152 shows the non-chiral molecule.
iupac name: 4-(trifluoromethyl)phenyl N-methyl-N-[(1s,4r)-4-{5-[methyl(prop-2-en-1-yl)amino]pentyl}cyclohexyl]carbamate
xref: CHEMBL1186073
approved: f
ligand name: compound 8 [PMID: 22533316]
type: SyntheticOrganicLigand

compound 5 [PMID: 22533316]
canonical SMILES: OCCN(CCCC#CC1CCC(CC1)N(C(=O)Oc1ccc(cc1)Cl)C)CC
in ch i key: UBLUCOHGNHINJX-XUTJKUGGSA-N
in ch i: InChI=1S/C23H33ClN2O3/c1-3-26(17-18-27)16-6-4-5-7-19-8-12-21(13-9-19)25(2)23(28)29-22-14-10-20(24)11-15-22/h10-11,14-15,19,21,27H,3-4,6,8-9,12-13,16-18H2,1-2H3/t19-,21-
comment: The structure of this ligand was drawn as shown in the listed reference. CID 10159157 shows the non-chiral compound.
iupac name: 4-chlorophenyl N-methyl-N-[(1r,4r)-4-{5-[ethyl(2-hydroxyethyl)amino]pent-1-yn-1-yl}cyclohexyl]carbamate
xref: CHEMBL2219906
approved: f
ligand name: compound 5 [PMID: 22533316]
type: SyntheticOrganicLigand

compound 4 [PMID: 22533316]
in ch i key: PDHRIPJKNGUCJP-UHFFFAOYSA-N
in ch i: InChI=1S/C21H23BrN2OS/c1-3-12-24(2)13-4-5-14-25-18-10-11-19-20(15-18)26-23-21(19)16-6-8-17(22)9-7-16/h3,6-11,15H,1,4-5,12-14H2,2H3
iupac name: 4-[[3-(4-bromophenyl)-1,2-benzothiazol-6-yl]oxy]-N-methyl-N-prop-2-enylbutan-1-amine
xref: CHEMBL516921
approved: f
ligand name: compound 4 [PMID: 22533316]
type: SyntheticOrganicLigand

compound 3 [PMID: 22533316]
in ch i key: XHOKJNHLSGAYJL-UHFFFAOYSA-N
iupac name: 2-[4-[[3-(4-bromophenyl)-1,2-benzothiazol-6-yl]oxy]butyl-ethylamino]ethanol
xref: CHEMBL1186807
approved: f
ligand name: compound 3 [PMID: 22533316]
type: SyntheticOrganicLigand

Ro 48-8071
in ch i key: CMYCCJYVZIMDFU-UHFFFAOYSA-N
in ch i: InChI=1S/C23H27BrFNO2/c1-3-14-26(2)15-6-4-5-7-16-28-20-12-13-21(22(25)17-20)23(27)18-8-10-19(24)11-9-18/h3,8-13,17H,1,4-7,14-16H2,2H3
iupac name: (4-bromophenyl)-[2-fluoro-4-[6-(methyl-prop-2-enylamino)hexoxy]phenyl]methanone
xref: CHEMBL304858
synonym: compound 2 [PMID: 22533316]
approved: f
ligand name: Ro 48-8071
type: SyntheticOrganicLigand

compound 1 [PMID: 22533316]
in ch i key: MCMDJJBPNGLKKM-UHFFFAOYSA-N
in ch i: InChI=1S/C24H22BrNO.ClH/c1-3-16-26(2)17-18-4-6-19(7-5-18)20-8-10-21(11-9-20)24(27)22-12-14-23(25)15-13-22;/h3-15H,1,16-17H2,2H3;1H
iupac name: [(4-{4-[(4-bromophenyl)carbonyl]phenyl}phenyl)methyl](methyl)(prop-2-en-1-yl)amine hydrochloride
xref: CHEMBL481608
approved: f
ligand name: compound 1 [PMID: 22533316]
type: SyntheticOrganicLigand

compound 4b [Marquart et al., 1994]
canonical SMILES: CCCCCCCCCCC1CCC2N(C1)CCCC2O
in ch i key: ASQOQJYHIYYTEJ-CEXWTWQISA-N
in ch i: InChI=1S/C19H37NO/c1-2-3-4-5-6-7-8-9-11-17-13-14-18-19(21)12-10-15-20(18)16-17/h17-19,21H,2-16H2,1H3/t17-,18+,19-/m1/s1
iupac name: (1R,7R,9aS)-7-decyl-octahydro-1H-quinolizin-1-ol
xref: CHEMBL278521
approved: f
ligand name: compound 4b [Marquart et al., 1994]
type: SyntheticOrganicLigand

compound 4a [Marquart et al., 1994]
canonical SMILES: CCCCCCCCCCC1CCC2N(C1)CCCC2O
in ch i key: ASQOQJYHIYYTEJ-GBESFXJTSA-N
in ch i: InChI=1S/C19H37NO/c1-2-3-4-5-6-7-8-9-11-17-13-14-18-19(21)12-10-15-20(18)16-17/h17-19,21H,2-16H2,1H3/t17-,18-,19+/m0/s1
iupac name: (1R,7S,9aS)-7-decyl-octahydro-1H-quinolizin-1-ol
xref: CHEMBL277446
approved: f
ligand name: compound 4a [Marquart et al., 1994]
type: SyntheticOrganicLigand

LSP4-2022
in ch i key: BGOFVWMHMQISHB-NKUHCKNESA-N
in ch i: InChI=1S/C13H18NO8P/c14-10(12(17)18)5-6-23(20,21)13(19)8-1-3-9(4-2-8)22-7-11(15)16/h1-4,10,13,19H,5-7,14H2,(H,15,16)(H,17,18)(H,20,21)/t10-,13?/m0/s1
iupac name: (2S)-2-amino-4-({[4-(carboxymethoxy)phenyl](hydroxy)methyl}(hydroxy)phosphoryl)butanoic acid
xref: CHEMBL3114673
approved: f
ligand name: LSP4-2022
type: SyntheticOrganicLigand

o-hydroxyatorvastatin
in ch i key: CZBPKFICAYVHHM-JWQCQUIFSA-N
in ch i: InChI=1S/C33H35FN2O6/c1-20(2)31-30(33(42)35-26-10-6-7-11-27(26)39)29(21-8-4-3-5-9-21)32(22-12-14-23(34)15-13-22)36(31)17-16-24(37)18-25(38)19-28(40)41/h3-15,20,24-25,37-39H,16-19H2,1-2H3,(H,35,42)(H,40,41)/t24-,25-/m1/s1
comment: One of the active metabolites of the approved drug atorvastatin.
iupac name: (3R,5R)-7-[2-(4-fluorophenyl)-4-[(2-hydroxyphenyl)carbamoyl]-3-phenyl-5-propan-2-ylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid
xref: CHEMBL1565
synonym: BMS-243887
approved: f
ligand name: o-hydroxyatorvastatin
type: SyntheticOrganicLigand

CP-775146
in ch i key: OISHBINQIFNIPV-JOCHJYFZSA-N
in ch i: InChI=1S/C26H33NO4/c1-18(2)20-12-10-19(11-13-20)15-24(28)27-14-6-8-22(17-27)21-7-5-9-23(16-21)31-26(3,4)25(29)30/h5,7,9-13,16,18,22H,6,8,14-15,17H2,1-4H3,(H,29,30)/t22-/m1/s1
iupac name: 2-methyl-2-[3-[(3S)-1-[2-(4-propan-2-ylphenyl)acetyl]piperidin-3-yl]phenoxy]propanoic acid
synonym: CP775146
approved: f
ligand name: CP-775146
type: SyntheticOrganicLigand

BigLEN
in ch i key: IPOOBASOJFKEAK-GTJGPZIJSA-N
comment: Naturally-occuring fragment of the endogenous peptide ProSAAS.
synonym: Big LEN
synonym: b-LEN
synonym: SAAS CT(25-40)
approved: f
ligand name: BigLEN
type: PeptideLigand

KH064
in ch i key: KWLUIYFCMHKLKY-NDEPHWFRSA-N
in ch i: InChI=1S/C31H37NO4/c33-30(16-10-2-1-5-11-25-12-6-3-7-13-25)32-28(19-22-31(34)35)23-26-17-20-29(21-18-26)36-24-27-14-8-4-9-15-27/h3-4,6-9,12-15,17-18,20-21,28H,1-2,5,10-11,16,19,22-24H2,(H,32,33)(H,34,35)/t28-/m0/s1
iupac name: (4S)-4-(7-phenylheptanoylamino)-5-[4-(phenylmethoxy)phenyl]pentanoic acid
xref: CHEMBL1084102
synonym: sPLA2-2A inhibitor, compound 2b
approved: f
ligand name: KH064
type: SyntheticOrganicLigand

compound 41 [PMID: 15026062]
in ch i key: XSLDWDIQZLTRHG-UHFFFAOYSA-N
in ch i: InChI=1S/C22H33N3O4/c1-22(2,3)17-6-4-16(5-7-17)20(26)23-18-8-10-19(11-9-18)29-21(27)24-25-12-14-28-15-13-25/h8-11,16-17H,4-7,12-15H2,1-3H3,(H,23,26)(H,24,27)
iupac name: [4-[(4-tert-butylcyclohexanecarbonyl)amino]phenyl] N-morpholin-4-ylcarbamate
xref: CHEMBL49895
approved: f
ligand name: compound 41 [PMID: 15026062]
type: SyntheticOrganicLigand

GR148672X
isomeric SMILES: Cc1cccc(c1)N/N=C(/C(=O)C(F)(F)F)/C(=O)c1cccs1
in ch i key: YNUQHMHMYSUKFL-NDENLUEZSA-N
iupac name: (2E)-4,4,4-trifluoro-2-[(3-methylphenyl)hydrazinylidene]-1-thiophen-2-ylbutane-1,3-dione
approved: f
ligand name: GR148672X
type: SyntheticOrganicLigand

prinaberel
canonical SMILES: C=Cc1cc(O)cc2c1oc(n2)c1ccc(c(c1)F)O
isomeric SMILES: C=Cc1cc(O)cc2c1oc(n2)c1ccc(c(c1)F)O
in ch i key: MQIMZDXIAHJKQP-UHFFFAOYSA-N
in ch i: InChI=1S/C15H10FNO3/c1-2-8-5-10(18)7-12-14(8)20-15(17-12)9-3-4-13(19)11(16)6-9/h2-7,18-19H,1H2
comment: Prinaberel is an estrogen receptor beta (ERβ) agonist, with potential gynecological uses and antiinflammatory action <Reference id=30684/><Reference id=30113/><Reference id=30683/>. The structure shown here matches that in the INN document for prinaberel, and as in the ChEMBL entry provided above. However, alternative tautomers are represented elsewhere including CID 5326893.
xref: CHEMBL450940
synonym: PF-00913086
synonym: ERB-041
synonym: ERB 041
approved: f
ligand name: prinaberel
type: SyntheticOrganicLigand

PB-28
canonical SMILES: COc1cccc2c1CCCC2CCCN1CCN(CC1)C1CCCCC1
isomeric SMILES: COc1cccc2c1CCCC2CCCN1CCN(CC1)C1CCCCC1
in ch i key: PHRCDWVPTULQMT-UHFFFAOYSA-N
in ch i: InChI=1S/C24H38N2O/c1-27-24-14-6-12-22-20(8-5-13-23(22)24)9-7-15-25-16-18-26(19-17-25)21-10-3-2-4-11-21/h6,12,14,20-21H,2-5,7-11,13,15-19H2,1H3
iupac name: 1-cyclohexyl-4-[3-(5-methoxy-1,2,3,4-tetrahydronaphthalen-1-yl)propyl]piperazine
xref: CHEMBL53325
synonym: PB28
approved: f
ligand name: PB-28
type: SyntheticOrganicLigand

fluticasone
in ch i key: MGNNYOODZCAHBA-GQKYHHCASA-N
in ch i: InChI=1S/C22H27F3O4S/c1-11-6-13-14-8-16(24)15-7-12(26)4-5-19(15,2)21(14,25)17(27)9-20(13,3)22(11,29)18(28)30-10-23/h4-5,7,11,13-14,16-17,27,29H,6,8-10H2,1-3H3/t11-,13+,14+,16+,17+,19+,20+,21+,22+/m1/s1
comment: The DrugBank entry listed here refers to fluticasone propionate with CAS registry number 80474-14-2. ChEMBL lists fluticasone propionate as a glucocorticoid receptor agonist, but not the fluticasone parent molecule. Breo Ellipta®, approved by the FDA in 2013, is a fixed-dose formulation containing fluticasone furoate and <Ligand id=7353/>.
iupac name: S-(fluoromethyl) (6S,8S,9R,10S,11S,13S,14S,16R,17R)-6,9-difluoro-11,17-dihydroxy-10,13,16-trimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthrene-17-carbothioate
xref: CHEMBL1201396
synonym: Avamys®
synonym: Advair®
synonym: Flovent HFA®
synonym: Veramyst®
approved: t
ligand name: fluticasone
type: SyntheticOrganicLigand

PF0998425
canonical SMILES: N#Cc1ccc(cc1C(F)(F)F)C1CCCCC1O
isomeric SMILES: N#Cc1ccc(cc1C(F)(F)F)[C@H]1CCCC[C@H]1O
in ch i key: MENRRRXHFQYXDW-DGCLKSJQSA-N
in ch i: InChI=1S/C14H14F3NO/c15-14(16,17)12-7-9(5-6-10(12)8-18)11-3-1-2-4-13(11)19/h5-7,11,13,19H,1-4H2/t11-,13-/m1/s1
iupac name: 4-[(1R,2R)-2-hydroxycyclohexyl]-2-(trifluoromethyl)benzonitrile
xref: CHEMBL458084
synonym: PF-998425
approved: f
ligand name: PF0998425
type: SyntheticOrganicLigand

GSK-264220A
in ch i key: LVOVQRPAMXCXTM-UHFFFAOYSA-N
in ch i: InChI=1S/C17H21N3O4S/c1-13-15(19-17(21)18-14-8-4-2-5-9-14)12-16(24-13)25(22,23)20-10-6-3-7-11-20/h2,4-5,8-9,12H,3,6-7,10-11H2,1H3,(H2,18,19,21)
comment: Due to the irreversible nature of this compound's inhibition it is not being progressed as a drug.
iupac name: 3-[2-methyl-5-(piperidine-1-sulfonyl)furan-3-yl]-1-phenylurea
xref: CHEMBL513349
approved: f
ligand name: GSK-264220A
type: SyntheticOrganicLigand

darapladib
in ch i key: WDPFJWLDPVQCAJ-UHFFFAOYSA-N
comment: Darapladib is a potent PLA2G7 (commonly referred to as Lp-PLA2) inhibitor. Darapladib and analogues such as <Ligand id=7376/> are clinical drug candidates with potential to reduce the risk of atherosclerosis and associated clinical sequelae <Reference id=24140/>.
xref: CHEMBL204021
synonym: SB-480848
synonym: SB 480848
approved: f
ligand name: darapladib
type: SyntheticOrganicLigand

BI6015
in ch i key: ILVCPQPMRPHZSG-UHFFFAOYSA-N
in ch i: InChI=1S/C15H13N3O4S/c1-10-7-8-12(18(19)20)9-15(10)23(21,22)17-11(2)16-13-5-3-4-6-14(13)17/h3-9H,1-2H3
iupac name: 2-methyl-1-(2-methyl-5-nitrophenyl)sulfonylbenzimidazole
synonym: BI-6015
synonym: BI 6015
approved: f
ligand name: BI6015
type: SyntheticOrganicLigand

PF-04457845
in ch i key: BATCTBJIJJEPHM-UHFFFAOYSA-N
in ch i: InChI=1S/C23H20F3N5O2/c24-23(25,26)18-6-7-21(27-15-18)33-19-4-1-3-17(14-19)13-16-8-11-31(12-9-16)22(32)29-20-5-2-10-28-30-20/h1-7,10,13-15H,8-9,11-12H2,(H,29,30,32)
comment: PF-04457845 is a highly selective, irreversible, covalent inactivator of fatty acid amide hydrolase (FAAH) <Reference id=22917/>, that is being investigated in clinical trials. It is one example from a dense analogoue series from patents (see 'Similar Compounds' in PubChem).
iupac name: N-pyridazin-3-yl-4-[[3-[5-(trifluoromethyl)pyridin-2-yl]oxyphenyl]methylidene]piperidine-1-carboxamide
xref: CHEMBL1651534
synonym: PF04457845
synonym: compound 23 [PMID: 21666860]
approved: f
ligand name: PF-04457845
type: SyntheticOrganicLigand

galantamine
canonical SMILES: COc1ccc2c3c1OC1C3(CCN(C2)C)C=CC(C1)O
in ch i key: ASUTZQLVASHGKV-JDFRZJQESA-N
in ch i: InChI=1S/C17H21NO3/c1-18-8-7-17-6-5-12(19)9-14(17)21-16-13(20-2)4-3-11(10-18)15(16)17/h3-6,12,14,19H,7-10H2,1-2H3/t12-,14-,17-/m0/s1
comment: Many alternative stereo forms exist for the structure. The marketed formulation contains galantamine hydrobromide (PubChem CID 121587).
iupac name: (1S,12S,14R)-9-methoxy-4-methyl-11-oxa-4-azatetracyclo[8.6.1.01,12.06,17]heptadeca-6(17),7,9,15-tetraen-14-ol
xref: CHEMBL659
synonym: galanthamine
synonym: Reminyl
synonym: Lycoremine
synonym: Razadyne®
synonym: Nivalin®
approved: t
ligand name: galantamine
type: SyntheticOrganicLigand

rasagiline
canonical SMILES: C#CCNC1CCc2c1cccc2
isomeric SMILES: C#CCN[C@@H]1CCc2c1cccc2
in ch i key: RUOKEQAAGRXIBM-GFCCVEGCSA-N
in ch i: InChI=1S/C12H13N/c1-2-9-13-12-8-7-10-5-3-4-6-11(10)12/h1,3-6,12-13H,7-9H2/t12-/m1/s1
comment: Marketed formulations may contain rasagiline mesylate (PubChem CID 3052775).
iupac name: (1R)-N-prop-2-ynyl-2,3-dihydro-1H-inden-1-amine
xref: CHEMBL887
synonym: Azilect®
synonym: TVP-1012
approved: t
ligand name: rasagiline
type: SyntheticOrganicLigand

[3H]folinic acid
in ch i key: VVIAGPKUTFNRDU-ABLWVSNPSA-N
in ch i: InChI=1S/C20H23N7O7/c21-20-25-16-15(18(32)26-20)27(9-28)12(8-23-16)7-22-11-3-1-10(2-4-11)17(31)24-13(19(33)34)5-6-14(29)30/h1-4,9,12-13,22H,5-8H2,(H,24,31)(H,29,30)(H,33,34)(H4,21,23,25,26,32)/t12?,13-/m0/s1
comment: Location of tritium is unknown.
xref: CHEMBL1679
approved: f
ligand name: [3H]folinic acid
type: SyntheticOrganicLigand

[3H]N5-methylfolate
in ch i key: ZNOVTXRBGFNYRX-UHFFFAOYSA-N
in ch i: InChI=1S/C20H25N7O6/c1-27-12(9-23-16-15(27)18(31)26-20(21)25-16)8-22-11-4-2-10(3-5-11)17(30)24-13(19(32)33)6-7-14(28)29/h2-5,12-13,22H,6-9H2,1H3,(H,24,30)(H,28,29)(H,32,33)(H4,21,23,25,26,31)
comment: Location of tritium is unknown.
iupac name: 2-[[4-[(2-amino-5-methyl-4-oxo-1,6,7,8-tetrahydropteridin-6-yl)methylamino]benzoyl]amino]pentanedioic acid
xref: CHEMBL2358502
approved: f
ligand name: [3H]N5-methylfolate
type: SyntheticOrganicLigand

[3H]pemetrexed
in ch i key: WBXPDJSOTKVWSJ-UHFFFAOYSA-N
in ch i: InChI=1S/C20H21N5O6/c21-20-24-16-15(18(29)25-20)12(9-22-16)6-3-10-1-4-11(5-2-10)17(28)23-13(19(30)31)7-8-14(26)27/h1-2,4-5,9,13H,3,6-8H2,(H,23,28)(H,26,27)(H,30,31)(H4,21,22,24,25,29)
comment: This compound is represented here in its non-isomeric form. R and S stereoisomers are represented elsewhere. Location of of tritium is unknown.
iupac name: 2-[[4-[2-(2-amino-4-oxo-1,7-dihydropyrrolo[4,5-e]pyrimidin-5-yl)ethyl]benzoyl]amino]pentanedioic acid
xref: CHEMBL59843
approved: f
ligand name: [3H]pemetrexed
type: SyntheticOrganicLigand

tacrine
canonical SMILES: Nc1c2CCCCc2nc2c1cccc2
isomeric SMILES: Nc1c2CCCCc2nc2c1cccc2
in ch i key: YLJREFDVOIBQDA-UHFFFAOYSA-N
in ch i: InChI=1S/C13H14N2/c14-13-9-5-1-3-7-11(9)15-12-8-4-2-6-10(12)13/h1,3,5,7H,2,4,6,8H2,(H2,14,15)
comment: Tacrine is a dual inhibitor of butyrylcholine esterase (P06276) and acetylcholinesterase (P22303). Marketed formulations may contain tacrine hydrochloride (PubChem CID 2723754).
iupac name: 1,2,3,4-tetrahydroacridin-9-amine
xref: CHEMBL95
synonym: Cognex®
synonym: CI-970
synonym: tetrahydroaminoacridine
approved: t
ligand name: tacrine
type: SyntheticOrganicLigand

[3H]-di-o-tolylguanidine
canonical SMILES: NC(=Nc1ccccc1C)Nc1ccccc1C
isomeric SMILES: NC(=Nc1ccccc1C)Nc1ccccc1C
in ch i key: OPNUROKCUBTKLF-UHFFFAOYSA-N
in ch i: InChI=1S/C15H17N3/c1-11-7-3-5-9-13(11)17-15(16)18-14-10-6-4-8-12(14)2/h3-10H,1-2H3,(H3,16,17,18)
iupac name: 1,2-bis(2-methylphenyl)guanidine
xref: CHEMBL282433
synonym: [3H]DOTG
approved: f
ligand name: [3H]-di-o-tolylguanidine
type: SyntheticOrganicLigand

1,3-ditolylguanidine
canonical SMILES: NC(=Nc1ccccc1C)Nc1ccccc1C
isomeric SMILES: NC(=Nc1ccccc1C)Nc1ccccc1C
in ch i key: OPNUROKCUBTKLF-UHFFFAOYSA-N
in ch i: InChI=1S/C15H17N3/c1-11-7-3-5-9-13(11)17-15(16)18-14-10-6-4-8-12(14)2/h3-10H,1-2H3,(H3,16,17,18)
iupac name: 1,2-bis(2-methylphenyl)guanidine
xref: CHEMBL282433
synonym: Di-o-tolylguanidine
synonym: 1,3-Di-o-tolylguanidine
synonym: DOTG
approved: f
ligand name: 1,3-ditolylguanidine
type: SyntheticOrganicLigand

[3H]pentazocine
canonical SMILES: CC(=CCN1CCC2(C(C1Cc1c2cc(cc1)O)C)C)C
in ch i key: VOKSWYLNZZRQPF-BXKNQVALSA-N
in ch i: InChI=1S/C19H27NO/c1-13(2)7-9-20-10-8-19(4)14(3)18(20)11-15-5-6-16(21)12-17(15)19/h5-7,12,14,18,21H,8-11H2,1-4H3/t14-,18+,19+/m1/s1/i6T,12T
xref: CHEMBL2311194
approved: f
ligand name: [3H]pentazocine
type: SyntheticOrganicLigand

SM 21
canonical SMILES: CCC(C(=O)OC1CC2CCC(C1)N2C)Oc1ccc(cc1)Cl
isomeric SMILES: CCC(C(=O)OC1CC2CCC(C1)N2C)Oc1ccc(cc1)Cl
in ch i key: WTPAXDRULIZRDJ-UHFFFAOYSA-N
in ch i: InChI=1S/C18H24ClNO3/c1-3-17(22-15-8-4-12(19)5-9-15)18(21)23-16-10-13-6-7-14(11-16)20(13)2/h4-5,8-9,13-14,16-17H,3,6-7,10-11H2,1-2H3
iupac name: (8-methyl-8-azabicyclo[3.2.1]octan-3-yl) 2-(4-chlorophenoxy)butanoate
xref: CHEMBL45951
synonym: SM-21
synonym: (RS)-SM21
synonym: (±)-SM21
approved: f
ligand name: SM 21
type: SyntheticOrganicLigand

clorgiline
canonical SMILES: C#CCN(CCCOc1ccc(cc1Cl)Cl)C
isomeric SMILES: C#CCN(CCCOc1ccc(cc1Cl)Cl)C
in ch i key: BTFHLQRNAMSNLC-UHFFFAOYSA-N
in ch i: InChI=1S/C13H15Cl2NO/c1-3-7-16(2)8-4-9-17-13-6-5-11(14)10-12(13)15/h1,5-6,10H,4,7-9H2,2H3
comment: Clorgiline is an analogue of <Ligand id=7262/>.
iupac name: N-[3-(2,4-dichlorophenoxy)propyl]-N-methylprop-2-yn-1-amine
xref: CHEMBL8706
synonym: chlorgyline
synonym: clorgyline
approved: f
ligand name: clorgiline
type: SyntheticOrganicLigand

NE-100
canonical SMILES: CCCN(CCc1ccc(c(c1)OCCc1ccccc1)OC)CCC
isomeric SMILES: CCCN(CCc1ccc(c(c1)OCCc1ccccc1)OC)CCC
in ch i key: YBLIQJGXRLZBCZ-UHFFFAOYSA-N
in ch i: InChI=1S/C23H33NO2/c1-4-15-24(16-5-2)17-13-21-11-12-22(25-3)23(19-21)26-18-14-20-9-7-6-8-10-20/h6-12,19H,4-5,13-18H2,1-3H3
iupac name: N-[2-[4-methoxy-3-(2-phenylethoxy)phenyl]ethyl]-N-propylpropan-1-amine
xref: CHEMBL190883
synonym: NE100
approved: f
ligand name: NE-100
type: SyntheticOrganicLigand

PRE-084
canonical SMILES: O=C(C1(CCCCC1)c1ccccc1)OCCN1CCOCC1
isomeric SMILES: O=C(C1(CCCCC1)c1ccccc1)OCCN1CCOCC1
in ch i key: RQHKZUBCUZVZEF-UHFFFAOYSA-N
in ch i: InChI=1S/C19H27NO3/c21-18(23-16-13-20-11-14-22-15-12-20)19(9-5-2-6-10-19)17-7-3-1-4-8-17/h1,3-4,7-8H,2,5-6,9-16H2
iupac name: 2-morpholin-4-ylethyl 1-phenylcyclohexane-1-carboxylate
xref: CHEMBL305881
synonym: PRE084
approved: f
ligand name: PRE-084
type: SyntheticOrganicLigand

(+)-SKF 10.047
canonical SMILES: C=CCN1CCC2(C(C1Cc1c2cc(cc1)O)C)C
in ch i key: LGQCVMYAEFTEFN-DQYPLSBCSA-N
in ch i: InChI=1S/C17H23NO/c1-4-8-18-9-7-17(3)12(2)16(18)10-13-5-6-14(19)11-15(13)17/h4-6,11-12,16,19H,1,7-10H2,2-3H3/t12-,16+,17+/m1/s1
synonym: (+)-SK&F10047
approved: f
ligand name: (+)-SKF 10.047
type: SyntheticOrganicLigand

(RS)-PPCC
in ch i key: BDSYECBSUUOPCT-UHFFFAOYSA-N
in ch i: InChI=1S/C24H29NO3/c1-18-8-10-20(11-9-18)24(22(26)28-2)16-21(24)17-25-14-12-23(27,13-15-25)19-6-4-3-5-7-19/h3-11,21,27H,12-17H2,1-2H3
iupac name: methyl 2-[(4-hydroxy-4-phenylpiperidin-1-yl)methyl]-1-(4-methylphenyl)cyclopropane-1-carboxylate
xref: CHEMBL222301
approved: f
ligand name: (RS)-PPCC
type: SyntheticOrganicLigand

PG01037
isomeric SMILES: O=C(c1ccc(cc1)c1ccccn1)NC/C=C/CN1CCN(CC1)c1cccc(c1Cl)Cl
in ch i key: ZMYOIZHRXABMFZ-ONEGZZNKSA-N
in ch i: InChI=1S/C26H26Cl2N4O/c27-22-6-5-8-24(25(22)28)32-18-16-31(17-19-32)15-4-3-14-30-26(33)21-11-9-20(10-12-21)23-7-1-2-13-29-23/h1-13H,14-19H2,(H,30,33)/b4-3+
iupac name: N-[(E)-4-[4-(2,3-dichlorophenyl)piperazin-1-yl]but-2-enyl]-4-pyridin-2-ylbenzamide
xref: CHEMBL180010
synonym: PG 01037
synonym: PG-01037
approved: f
ligand name: PG01037
type: SyntheticOrganicLigand

NGB 2904
in ch i key: YJPWVCIGSHWNON-UHFFFAOYSA-N
in ch i: InChI=1S/C28H29Cl2N3O/c29-25-8-5-9-26(27(25)30)33-16-14-32(15-17-33)13-4-3-12-31-28(34)21-10-11-24-22(19-21)18-20-6-1-2-7-23(20)24/h1-2,5-11,19H,3-4,12-18H2,(H,31,34)
iupac name: N-[4-[4-(2,3-dichlorophenyl)piperazin-1-yl]butyl]-9H-fluorene-2-carboxamide
xref: CHEMBL300780
synonym: NGB-2904
approved: f
ligand name: NGB 2904
type: SyntheticOrganicLigand

9-cis-retinal
canonical SMILES: O=CC=C(C=CC=C(C=CC1=C(C)CCCC1(C)C)C)C
isomeric SMILES: O=C/C=C(/C=C/C=C(/C=C/C1=C(C)CCCC1(C)C)/C)/C
in ch i key: NCYCYZXNIZJOKI-MKOSUFFBSA-N
in ch i: InChI=1S/C20H28O/c1-16(8-6-9-17(2)13-15-21)11-12-19-18(3)10-7-14-20(19,4)5/h6,8-9,11-13,15H,7,10,14H2,1-5H3/b9-6+,12-11+,16-8-,17-13+
iupac name: (2E,4E,6Z,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)nona-2,4,6,8-tetraenal
xref: CHEMBL257381
synonym: 9-cis-retinal
synonym: 9-cis-retinaldehyde
approved: f
ligand name: 9-cis-retinal
type: MetaboliteLigand

13-cis-retinol
canonical SMILES: OCC=C(C=CC=C(C=CC1=C(C)CCCC1(C)C)C)C
isomeric SMILES: OC/C=C(/C=C/C=C(/C=C/C1=C(C)CCCC1(C)C)/C)/C
in ch i key: FPIPGXGPPPQFEQ-HWCYFHEPSA-N
in ch i: InChI=1S/C20H30O/c1-16(8-6-9-17(2)13-15-21)11-12-19-18(3)10-7-14-20(19,4)5/h6,8-9,11-13,21H,7,10,14-15H2,1-5H3/b9-6+,12-11+,16-8+,17-13-
iupac name: (2Z,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)nona-2,4,6,8-tetraen-1-ol
xref: CHEMBL1454290
synonym: 13-cis-retinol
synonym: neovitamin A
approved: f
ligand name: 13-cis-retinol
type: MetaboliteLigand

13-cis-retinal
canonical SMILES: O=CC=C(C=CC=C(C=CC1=C(C)CCCC1(C)C)C)C
isomeric SMILES: O=C/C=C(/C=C/C=C(/C=C/C1=C(C)CCCC1(C)C)/C)/C
in ch i key: NCYCYZXNIZJOKI-HWCYFHEPSA-N
in ch i: InChI=1S/C20H28O/c1-16(8-6-9-17(2)13-15-21)11-12-19-18(3)10-7-14-20(19,4)5/h6,8-9,11-13,15H,7,10,14H2,1-5H3/b9-6+,12-11+,16-8+,17-13-
iupac name: (2Z,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)nona-2,4,6,8-tetraenal
xref: CHEMBL1579130
synonym: 13-cis-retinal
synonym: 13-cis-retinaldehyde
approved: f
ligand name: 13-cis-retinal
type: MetaboliteLigand

11-cis-retinol
canonical SMILES: OCC=C(C=CC=C(C=CC1=C(C)CCCC1(C)C)C)C
isomeric SMILES: OC/C=C(/C=C/C=C(/C=C/C1=C(C)CCCC1(C)C)/C)/C
in ch i key: FPIPGXGPPPQFEQ-IOUUIBBYSA-N
in ch i: InChI=1S/C20H30O/c1-16(8-6-9-17(2)13-15-21)11-12-19-18(3)10-7-14-20(19,4)5/h6,8-9,11-13,21H,7,10,14-15H2,1-5H3/b9-6-,12-11+,16-8+,17-13+
iupac name: (2E,4Z,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)nona-2,4,6,8-tetraen-1-ol
synonym: 11-cis-retinol
approved: f
ligand name: 11-cis-retinol
type: MetaboliteLigand

11-cis-retinal
canonical SMILES: O=CC=C(C=CC=C(C=CC1=C(C)CCCC1(C)C)C)C
isomeric SMILES: O=C/C=C(/C=C/C=C(/C=C/C1=C(C)CCCC1(C)C)/C)/C
in ch i key: NCYCYZXNIZJOKI-IOUUIBBYSA-N
in ch i: InChI=1S/C20H28O/c1-16(8-6-9-17(2)13-15-21)11-12-19-18(3)10-7-14-20(19,4)5/h6,8-9,11-13,15H,7,10,14H2,1-5H3/b9-6-,12-11+,16-8+,17-13+
iupac name: (2E,4Z,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)nona-2,4,6,8-tetraenal
xref: CHEMBL1255087
synonym: 11-cis-retinal
synonym: retinaldehyde
synonym: 11-cis-retinaldehyde
approved: f
ligand name: 11-cis-retinal
type: MetaboliteLigand

NVP 231
in ch i key: MVSSJPGNLQPWSW-UHFFFAOYSA-N
in ch i: InChI=1S/C25H25N3O2S/c29-22(18-4-2-1-3-5-18)28-24-27-20-7-6-19(11-21(20)31-24)26-23(30)25-12-15-8-16(13-25)10-17(9-15)14-25/h1-7,11,15-17H,8-10,12-14H2,(H,26,30)(H,27,28,29)
iupac name: N-[2-(benzoylamino)-1,3-benzothiazol-6-yl]adamantane-1-carboxamide
synonym: NVP231
synonym: NVP-231
approved: f
ligand name: NVP 231
type: SyntheticOrganicLigand

[125I]-BDZ2
in ch i key: VLKJKVMACAESPP-MRDSYVANSA-N
in ch i: InChI=1S/C23H19IN4O2/c1-28-19-13-6-5-12-18(19)20(15-8-3-2-4-9-15)26-21(22(28)29)27-23(30)25-17-11-7-10-16(24)14-17/h2-14,21H,1H3,(H2,25,27,30)/t21-/m0/s1/i24-2
iupac name: 1-(3-iodanylphenyl)-3-[(3R)-1-methyl-2-oxo-5-phenyl-3H-1,4-benzodiazepin-3-yl]urea
xref: CHEMBL515288
approved: f
ligand name: [125I]-BDZ2
type: SyntheticOrganicLigand

JNJ-26070109
in ch i key: TZKCPFFVWLRNRZ-CYBMUJFWSA-N
iupac name: 4-bromo-N-[(1R)-1-(2,4-difluorophenyl)ethyl]-2-(quinoxalin-5-ylsulfonylamino)benzamide
synonym: JNJ26070109
approved: f
ligand name: JNJ-26070109
type: SyntheticOrganicLigand

myriocin
isomeric SMILES: CCCCCCC(=O)CCCCCC/C=C/C[C@H]([C@@H]([C@](C(=O)O)(CO)N)O)O
in ch i key: ZZIKIHCNFWXKDY-GNTQXERDSA-N
in ch i: InChI=1S/C21H39NO6/c1-2-3-4-10-13-17(24)14-11-8-6-5-7-9-12-15-18(25)19(26)21(22,16-23)20(27)28/h9,12,18-19,23,25-26H,2-8,10-11,13-16,22H2,1H3,(H,27,28)/b12-9+/t18-,19+,21+/m1/s1
comment: Myriocin is a sphingosine-like potent immunosuppressant acting primarily via inhibition of serine palmitoyltransferase which catalyses the first step of sphingolipid biosynthesis <Reference id=22654/>. The compound was originally isolated from the fungus Isaria sinclarii.
iupac name: (E,2S,3R,4R)-2-amino-3,4-dihydroxy-2-(hydroxymethyl)-14-oxoicos-6-enoic acid
xref: CHEMBL55076
synonym: ISP-1
synonym: thermozymocidin
approved: f
ligand name: myriocin
type: SyntheticOrganicLigand

4-hydroxyphenyl acetaldehyde
canonical SMILES: O=CCc1ccc(cc1)O
isomeric SMILES: O=CCc1ccc(cc1)O
in ch i key: IPRPPFIAVHPVJH-UHFFFAOYSA-N
in ch i: InChI=1S/C8H8O2/c9-6-5-7-1-3-8(10)4-2-7/h1-4,6,10H,5H2
iupac name: 2-(4-hydroxyphenyl)acetaldehyde
synonym: p-hydroxyphenylacetaldehyde
approved: f
ligand name: 4-hydroxyphenyl acetaldehyde
type: SyntheticOrganicLigand

HQL-79
in ch i key: TZQGXAHOROZEKN-UHFFFAOYSA-N
in ch i: InChI=1S/C22H27N5O/c1-3-8-18(9-4-1)22(19-10-5-2-6-11-19)28-20-13-16-27(17-14-20)15-7-12-21-23-25-26-24-21/h1-6,8-11,20,22H,7,12-17H2,(H,23,24,25,26)
iupac name: 4-[di(phenyl)methoxy]-1-[3-(2H-tetrazol-5-yl)propyl]piperidine
xref: CHEMBL574003
synonym: HQL 79
synonym: HQL79
approved: f
ligand name: HQL-79
type: SyntheticOrganicLigand

ketorolac
canonical SMILES: OC(=O)C1CCn2c1ccc2C(=O)c1ccccc1
isomeric SMILES: OC(=O)C1CCn2c1ccc2C(=O)c1ccccc1
in ch i key: OZWKMVRBQXNZKK-UHFFFAOYSA-N
in ch i: InChI=1S/C15H13NO3/c17-14(10-4-2-1-3-5-10)13-7-6-12-11(15(18)19)8-9-16(12)13/h1-7,11H,8-9H2,(H,18,19)
comment: Ketorolac is a heterocyclic acetic acid class non-steroidal anti-inflammatory drug (NSAID). It acts as a non-selective COX inhibitor. The administered drug is a racemic mixture of enantiomers. We show the chemical structure without specified stereochemistry to represent the mixture.
iupac name: 5-(benzoyl)-2,3-dihydro-1H-pyrrolizine-1-carboxylic acid
xref: CHEMBL469
synonym: Macril
synonym: Sprix
synonym: Toradol®
synonym: Acular®
approved: t
ligand name: ketorolac
type: SyntheticOrganicLigand

GB88
in ch i key: DCUDDCGUKZLQLN-ZEZZXZOMSA-N
in ch i: InChI=1S/C32H42N4O4/c1-3-22(2)28(31(39)36-19-16-32(17-20-36)15-13-24-11-7-8-12-25(24)32)35-29(37)26(21-23-9-5-4-6-10-23)34-30(38)27-14-18-33-40-27/h7-8,11-15,18,22-23,26,28H,3-6,9-10,16-17,19-21H2,1-2H3,(H,34,38)(H,35,37)/t22-,26+,28+/m1/s1
comment: GB88 is a PAR2 receptor antagonist <Reference id=31447/>. It inhibits the proinflammatory and pronociceptive actions of trypsin, cathepsin-S and elastase, consistent with the observation that PAR2 deletion inhibits trypsin-, cathepsin-S- and elastase-induced inflammation and nociception <Reference id=31447/>.
iupac name: N-[(2S)-3-cyclohexyl-1-[[(2S,3R)-3-methyl-1-oxo-1-spiro[indene-1,4'-piperidine]-1'-ylpentan-2-yl]amino]-1-oxopropan-2-yl]-1,2-oxazole-5-carboxamide
xref: CHEMBL2431617
synonym: GB 88
synonym: GB-88
approved: f
ligand name: GB88
type: SyntheticOrganicLigand

GB110
in ch i key: HXLQLJFWNKMGET-KCPQSXFMSA-N
in ch i: InChI=1S/C33H48N6O5/c1-3-22(2)29(38-30(40)27(19-23-8-5-4-6-9-23)37-31(41)28-12-15-36-44-28)32(42)35-21-25-10-7-11-26(18-25)33(43)39-16-13-24(20-34)14-17-39/h7,10-12,15,18,22-24,27,29H,3-6,8-9,13-14,16-17,19-21,34H2,1-2H3,(H,35,42)(H,37,41)(H,38,40)/t22?,27-,29-/m0/s1
iupac name: N-[(2S)-1-[[(2S)-1-[[3-[4-(aminomethyl)piperidine-1-carbonyl]phenyl] methylamino]-3-methyl-1-oxopentan-2-yl]amino]-3-cyclohexyl-1-oxopropan- 2-yl]-1,2-oxazole-5-carboxamide
synonym: GB 110
synonym: GB-110
approved: f
ligand name: GB110
type: SyntheticOrganicLigand

3-ketosphinganine
canonical SMILES: CCCCCCCCCCCCCCCC(=O)C(CO)N
isomeric SMILES: CCCCCCCCCCCCCCCC(=O)[C@H](CO)N
in ch i key: KBUNOSOGGAARKZ-KRWDZBQOSA-N
in ch i: InChI=1S/C18H37NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-18(21)17(19)16-20/h17,20H,2-16,19H2,1H3/t17-/m0/s1
iupac name: (2S)-2-amino-1-hydroxyoctadecan-3-one
synonym: ketodihydrosphingosine
synonym: 3-dehydrosphinganine
synonym: 3-ketodihydrosphingosine
synonym: 3-dehydro-D-sphinganine
approved: f
ligand name: 3-ketosphinganine
type: MetaboliteLigand

CZC 24832
in ch i key: RXRZPHQBTHQXSV-UHFFFAOYSA-N
in ch i: InChI=1S/C15H17FN6O2S/c1-15(2,3)21-25(23,24)11-4-9(6-18-7-11)10-5-12(16)13-19-14(17)20-22(13)8-10/h4-8,21H,1-3H3,(H2,17,20)
comment: CZC24832 is the first reported selective PI3Kγ inhibitor <Reference id=22557/>. The activity of CZC24832 has been investigated in preclinical studies.
iupac name: 5-{2-amino-8-fluoro-[1,2,4]triazolo[1,5-a]pyridin-6-yl}-N-tert-butylpyridine-3-sulfonamide
xref: CHEMBL2064571
synonym: CZC-24832
synonym: CZC24832
approved: f
ligand name: CZC 24832
type: SyntheticOrganicLigand

3,5-diiodo-L-tyrosine
canonical SMILES: OC(=O)C(Cc1cc(I)c(c(c1)I)O)N
isomeric SMILES: OC(=O)[C@H](Cc1cc(I)c(c(c1)I)O)N
in ch i key: NYPYHUZRZVSYKL-ZETCQYMHSA-N
in ch i: InChI=1S/C9H9I2NO3/c10-5-1-4(2-6(11)8(5)13)3-7(12)9(14)15/h1-2,7,13H,3,12H2,(H,14,15)/t7-/m0/s1
iupac name: (2S)-2-amino-3-(4-hydroxy-3,5-diiodophenyl)propanoic acid
xref: CHEMBL1236469
synonym: diotyrosine
synonym: 3,5-diiodotyrosine
approved: f
ligand name: 3,5-diiodo-L-tyrosine
type: SyntheticOrganicLigand

propylthiouracil
canonical SMILES: CCCc1cc(=O)[nH]c(=S)[nH]1
isomeric SMILES: CCCc1cc(=O)[nH]c(=S)[nH]1
in ch i key: KNAHARQHSZJURB-UHFFFAOYSA-N
in ch i: InChI=1S/C7H10N2OS/c1-2-3-5-4-6(10)9-7(11)8-5/h4H,2-3H2,1H3,(H2,8,9,10,11)
comment: Propylthiouracil is a thiouracil-derived drug, which acts as a thyroperoxidase inhibitor. Propylthiouracil is on the World Health Organisation's List of Essential Medicines. Click here to access the pdf version of the WHO's 21st Essential Medicines list (2019).
iupac name: 6-propyl-2-sulfanylidene-1H-pyrimidin-4-one
xref: CHEMBL1518
synonym: Thyreostat II
synonym: Thyreostat®
synonym: Propacil
synonym: Prothyran
approved: t
ligand name: propylthiouracil
type: SyntheticOrganicLigand

methimazole
canonical SMILES: Cn1ccnc1S
isomeric SMILES: Cn1ccnc1S
in ch i key: PMRYVIKBURPHAH-UHFFFAOYSA-N
in ch i: InChI=1S/C4H6N2S/c1-6-3-2-5-4(6)7/h2-3H,1H3,(H,5,7)
comment: Methimazole is a thioamide antithyroid drug which acts as a thyroperoxidase inhibitor and reduces serum CXCL10 (a chemokine that participates in the self-perpetuation of the inflammatory processes in patients with autoimmune thyroid disease) from thyrocytes <Reference id=31239/>.
iupac name: 1-methyl-3H-imidazole-2-thione
xref: CHEMBL1515
synonym: Basolan
synonym: Danantizol
synonym: Favistan
synonym: Frentirox
synonym: Merkastan
synonym: Metizol
synonym: Metotirin
synonym: Strumazol
synonym: Strumazole
synonym: Tapuzole
synonym: Thacapzol
synonym: Thycapsol
synonym: Thycapzol
synonym: Tapazole®
synonym: Thiamazole®
approved: t
ligand name: methimazole
type: SyntheticOrganicLigand

T2
canonical SMILES: OC(=O)C(Cc1ccc(c(c1)I)Oc1ccc(c(c1)I)O)N
isomeric SMILES: OC(=O)C(Cc1ccc(c(c1)I)Oc1ccc(c(c1)I)O)N
in ch i key: CPCJBZABTUOGNM-UHFFFAOYSA-N
in ch i: InChI=1S/C15H13I2NO4/c16-10-7-9(2-3-13(10)19)22-14-4-1-8(5-11(14)17)6-12(18)15(20)21/h1-5,7,12,19H,6,18H2,(H,20,21)
iupac name: 2-amino-3-[4-(4-hydroxy-3-iodophenoxy)-3-iodophenyl]propanoic acid
xref: CHEMBL1743303
synonym: 3,3'-diiodothyronine
synonym: T2
approved: f
ligand name: T2
type: SyntheticOrganicLigand

entacapone
canonical SMILES: CCN(C(=O)C(=Cc1cc(O)c(c(c1)[N+](=O)[O-])O)C#N)CC
isomeric SMILES: CCN(C(=O)/C(=C/c1cc(O)c(c(c1)[N+](=O)[O-])O)/C#N)CC
in ch i key: JRURYQJSLYLRLN-BJMVGYQFSA-N
in ch i: InChI=1S/C14H15N3O5/c1-3-16(4-2)14(20)10(8-15)5-9-6-11(17(21)22)13(19)12(18)7-9/h5-7,18-19H,3-4H2,1-2H3/b10-5+
comment: Entacapone inhibits catechol O-methyltransferase (COMT).
iupac name: (E)-2-cyano-3-(3,4-dihydroxy-5-nitrophenyl)-N,N-diethylprop-2-enamide
xref: CHEMBL953
synonym: OR-611
synonym: Comtan®
synonym: Comtess®
approved: t
ligand name: entacapone
type: SyntheticOrganicLigand

pirlindole
canonical SMILES: Cc1ccc2c(c1)c1CCCC3c1n2CCN3
isomeric SMILES: Cc1ccc2c(c1)c1CCCC3c1n2CCN3
in ch i key: IWVRVEIKCBFZNF-UHFFFAOYSA-N
in ch i: InChI=1S/C15H18N2/c1-10-5-6-14-12(9-10)11-3-2-4-13-15(11)17(14)8-7-16-13/h5-6,9,13,16H,2-4,7-8H2,1H3
comment: Pirlindole is a reversible monoamine oxidase A inhibitor (RIMA) family antidepressant.
iupac name: 8-Methyl-2,3,3a,4,5,6-hexahydro-1H-pyrazino[3,2,1-jk]carbazole
xref: CHEMBL32350
synonym: Pyrazidol ®
synonym: lifril
approved: t
ligand name: pirlindole
type: SyntheticOrganicLigand

befloxatone
in ch i key: IALVDLPLCLFBCF-CHWSQXEVSA-N
in ch i: InChI=1S/C15H18F3NO5/c1-22-9-12-8-19(14(21)24-12)10-2-4-11(5-3-10)23-7-6-13(20)15(16,17)18/h2-5,12-13,20H,6-9H2,1H3/t12-,13-/m1/s1
iupac name: (5R)-5-(methoxymethyl)-3-[4-[(3R)-4,4,4-trifluoro-3-hydroxybutoxy]phenyl]-1,3-oxazolidin-2-one
xref: CHEMBL416578
synonym: MD370503
approved: f
ligand name: befloxatone
type: SyntheticOrganicLigand

nepicastat
canonical SMILES: NCc1c[nH]c(=S)n1C1CCc2c(C1)cc(cc2F)F
in ch i key: YZZVIKDAOTXDEB-JTQLQIEISA-N
in ch i: InChI=1S/C14H15F2N3S/c15-9-3-8-4-10(1-2-12(8)13(16)5-9)19-11(6-17)7-18-14(19)20/h3,5,7,10H,1-2,4,6,17H2,(H,18,20)/t10-/m0/s1
iupac name: 5-(aminomethyl)-1-[(2S)-5,7-difluoro-1,2,3,4-tetrahydronaphthalen-2-yl]-3H-imidazole-2-thione
xref: CHEMBL1188395
synonym: SYN117
synonym: RS-25560-197
approved: f
ligand name: nepicastat
type: SyntheticOrganicLigand

4-hydroxyphenylpyruvic acid
canonical SMILES: Oc1ccc(cc1)CC(=O)C(=O)O
isomeric SMILES: Oc1ccc(cc1)CC(=O)C(=O)O
in ch i key: KKADPXVIOXHVKN-UHFFFAOYSA-N
in ch i: InChI=1S/C9H8O4/c10-7-3-1-6(2-4-7)5-8(11)9(12)13/h1-4,10H,5H2,(H,12,13)
iupac name: 3-(4-Hydroxyphenyl)-2-oxopropanoic acid
xref: CHEMBL607712
synonym: 4-hydroxyphenylpyruvate
approved: f
ligand name: 4-hydroxyphenylpyruvic acid
type: MetaboliteLigand

phosphoethanolamine
canonical SMILES: [NH3+]CCOP(=O)([O-])[O-]
isomeric SMILES: [NH3+]CCOP(=O)([O-])[O-]
in ch i key: SUHOOTKUPISOBE-UHFFFAOYSA-M
in ch i: InChI=1S/C2H8NO4P/c3-1-2-7-8(4,5)6/h1-3H2,(H2,4,5,6)/p-1
iupac name: 2-azaniumylethyl phosphate
synonym: 2-ammonioethyl phosphate
synonym: O-phosphonatoethanaminium
approved: f
ligand name: phosphoethanolamine
type: SyntheticOrganicLigand

ROMe
canonical SMILES: CCCCCCCCc1ccc(cc1)CCC(COC)(CO)N
isomeric SMILES: CCCCCCCCc1ccc(cc1)CC[C@](COC)(CO)N
in ch i key: YEYZALQTJCVXIJ-HXUWFJFHSA-N
in ch i: InChI=1S/C20H35NO2/c1-3-4-5-6-7-8-9-18-10-12-19(13-11-18)14-15-20(21,16-22)17-23-2/h10-13,22H,3-9,14-17,21H2,1-2H3/t20-/m1/s1
comment: ROMe is a synthetic sphingosine analogue.
iupac name: (2R)-2-amino-2-(methoxymethyl)-4-(4-octylphenyl)butan-1-ol
xref: CHEMBL2158686
synonym: (R)-FTY720 methyl ether
synonym: (R)-FTY720-OMe
approved: f
ligand name: ROMe
type: SyntheticOrganicLigand

opaganib
in ch i key: CAOTVXGYTWCKQE-UHFFFAOYSA-N
in ch i: InChI=1S/C23H25ClN2O/c24-20-3-1-19(2-4-20)22-10-17-9-18(11-22)13-23(12-17,15-22)21(27)26-14-16-5-7-25-8-6-16/h1-8,17-18H,9-15H2,(H,26,27)
comment: Opaganib (ABC294640) is an orally bioavailable sphingosine kinase 2-selective inhibitor that is being investigated for clinical antiproliferative efficacy in various cancers <Reference id=39787/>. The sphingosine kinases (SK1 and SK2) are key enzymes within the sphingolipid metabolism pathway that promote tumour growth and pathologic inflammation. Opaganib is being developed by RedHill Bio. In 2017 the FDA granted this compound orphan designation for the treatment of cholangiocarcinoma. SARS-CoV-2 and COVID-19: A medRxiv preprint descibes the compassionate use of opaganib in a small cohort of patients with severe COVID-19 <Reference id=39786/>, predicated upon the drug's anti-inflammatory and anti-viral properties. The analysis indicated trends in favour of clinical efficacy which led to extended investigation in a Phase 2 randomised placebo-controlled trial.
iupac name: 3-(4-chlorophenyl)-N-(pyridin-4-ylmethyl)adamantane-1-carboxamide
xref: CHEMBL2158685
synonym: Yeliva®
synonym: ABC-294640
synonym: ABC 294640
approved: f
ligand name: opaganib
type: SyntheticOrganicLigand

PF-543
in ch i key: NPUXORBZRBIOMQ-RUZDIDTESA-N
in ch i: InChI=1S/C27H31NO4S/c1-21-14-24(20-33(30,31)27-7-3-2-4-8-27)16-26(15-21)32-19-23-11-9-22(10-12-23)17-28-13-5-6-25(28)18-29/h2-4,7-12,14-16,25,29H,5-6,13,17-20H2,1H3/t25-/m1/s1
comment: PF-543 is a selective inhibitor of sphingosine kinase-1 <Reference id=22436/>. It is >100-fold selective for SphK1 over the SphK2 isoform.
xref: CHEMBL3134157
synonym: PF 543
synonym: compound 22a [PMID: 22397330]
synonym: sphingosine kinase 1 Inhibitor II
approved: f
ligand name: PF-543
type: SyntheticOrganicLigand

SK1-I
canonical SMILES: CCCCCc1ccc(cc1)C=CC(C(NC)CO)O
isomeric SMILES: CCCCCc1ccc(cc1)/C=C/[C@@H]([C@H](NC)CO)O
in ch i key: JYEXUQKROPHSEF-SFDDJJRUSA-N
in ch i: InChI=1S/C17H27NO2/c1-3-4-5-6-14-7-9-15(10-8-14)11-12-17(20)16(13-19)18-2/h7-12,16-20H,3-6,13H2,1-2H3/b12-11+/t16-,17+/m1/s1
iupac name: (2R,3S,4E)-2-(methylamino)-5-(4-pentylphenyl)pent-4-ene-1,3-diol
xref: CHEMBL2376441
synonym: BML-258
approved: f
ligand name: SK1-I
type: SyntheticOrganicLigand

sphinganine 1-phosphate
canonical SMILES: CCCCCCCCCCCCCCCC(C(COP(=O)([O-])[O-])[NH3+])O
isomeric SMILES: CCCCCCCCCCCCCCC[C@H]([C@H](COP(=O)([O-])[O-])[NH3+])O
in ch i key: YHEDRJPUIRMZMP-ZWKOTPCHSA-M
in ch i: InChI=1S/C18H40NO5P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-18(20)17(19)16-24-25(21,22)23/h17-18,20H,2-16,19H2,1H3,(H2,21,22,23)/p-1/t17-,18+/m0/s1
comment: Sphinganine-1-phosphate is an endogenous bioactive lipid. It is produced from sphinganine in the presence of sphingosine kinase.
iupac name: (2S,3R)-2-azaniumyl-3-hydroxyoctadecyl phosphate
synonym: sphinganine 1-phosphate
approved: f
ligand name: sphinganine 1-phosphate
type: MetaboliteLigand

2-methyl-3-oxopropanoate
canonical SMILES: O=CC(C(=O)[O-])C
isomeric SMILES: O=CC(C(=O)[O-])C
in ch i key: VOKUMXABRRXHAR-UHFFFAOYSA-M
in ch i: InChI=1S/C4H6O3/c1-3(2-5)4(6)7/h2-3H,1H3,(H,6,7)/p-1
iupac name: 2-methyl-3-oxopropanoate
approved: f
ligand name: 2-methyl-3-oxopropanoate
type: MetaboliteLigand

(S)-3-amino-2-methylpropanoate
canonical SMILES: [O-]C(=O)C(C[NH3+])C
isomeric SMILES: [O-]C(=O)[C@H](C[NH3+])C
in ch i key: QCHPKSFMDHPSNR-VKHMYHEASA-N
in ch i: InChI=1S/C4H9NO2/c1-3(2-5)4(6)7/h3H,2,5H2,1H3,(H,6,7)/t3-/m0/s1
iupac name: (2S)-3-azaniumyl-2-methylpropanoate
approved: f
ligand name: (S)-3-amino-2-methylpropanoate
type: MetaboliteLigand

4-oxobutanoate
canonical SMILES: O=CCCC(=O)[O-]
isomeric SMILES: O=CCCC(=O)[O-]
in ch i key: UIUJIQZEACWQSV-UHFFFAOYSA-M
in ch i: InChI=1S/C4H6O3/c5-3-1-2-4(6)7/h3H,1-2H2,(H,6,7)/p-1
iupac name: 4-oxobutanoate
synonym: succinate semialdehyde
approved: f
ligand name: 4-oxobutanoate
type: MetaboliteLigand

4-aminobutanal
canonical SMILES: NCCCC=O
isomeric SMILES: NCCCC=O
in ch i key: DZQLQEYLEYWJIB-UHFFFAOYSA-N
in ch i: InChI=1S/C4H9NO/c5-3-1-2-4-6/h4H,1-3,5H2
iupac name: 4-aminobutanal
xref: CHEMBL2261442
approved: f
ligand name: 4-aminobutanal
type: MetaboliteLigand

4-trimethylammoniobutanoate
canonical SMILES: [O-]C(=O)CCC[N+](C)(C)C
isomeric SMILES: [O-]C(=O)CCC[N+](C)(C)C
in ch i key: JHPNVNIEXXLNTR-UHFFFAOYSA-N
in ch i: InChI=1S/C7H15NO2/c1-8(2,3)6-4-5-7(9)10/h4-6H2,1-3H3
iupac name: 4-trimethylazaniumylbutanoate
xref: CHEMBL2074645
approved: f
ligand name: 4-trimethylammoniobutanoate
type: MetaboliteLigand

4-trimethylammoniobutanal
canonical SMILES: O=CCCC[N+](C)(C)C
isomeric SMILES: O=CCCC[N+](C)(C)C
in ch i key: OITBLCDWXSXNCN-UHFFFAOYSA-N
in ch i: InChI=1S/C7H16NO/c1-8(2,3)6-4-5-7-9/h7H,4-6H2,1-3H3/q+1
iupac name: trimethyl-(4-oxobutyl)azanium
approved: f
ligand name: 4-trimethylammoniobutanal
type: MetaboliteLigand

rivastigmine
canonical SMILES: CCN(C(=O)Oc1cccc(c1)C(N(C)C)C)C
isomeric SMILES: CCN(C(=O)Oc1cccc(c1)[C@@H](N(C)C)C)C
in ch i key: XSVMFMHYUFZWBK-NSHDSACASA-N
in ch i: InChI=1S/C14H22N2O2/c1-6-16(5)14(17)18-13-9-7-8-12(10-13)11(2)15(3)4/h7-11H,6H2,1-5H3/t11-/m0/s1
comment: Marketed formulations may contain rivastigmine hydrogen tartrate (PubChem CID 14254240).
iupac name: [3-[(1S)-1-dimethylaminoethyl]phenyl] N-ethyl-N-methylcarbamate
xref: CHEMBL636
synonym: Ena 713 free base
synonym: Exelon Patch
synonym: Exelon®
synonym: Nimvastid
synonym: Prometax
approved: t
ligand name: rivastigmine
type: SyntheticOrganicLigand

bambuterol
in ch i key: ANZXOIAKUNOVQU-UHFFFAOYSA-N
in ch i: InChI=1S/C18H29N3O5/c1-18(2,3)19-11-15(22)12-8-13(25-16(23)20(4)5)10-14(9-12)26-17(24)21(6)7/h8-10,15,19,22H,11H2,1-7H3
comment: Bambuterol has marketing approval in many countries but is not approved for sale in the US or UK.
iupac name: [3-[2-(tert-butylamino)-1-hydroxyethyl]-5-(dimethylcarbamoyloxy)phenyl] N,N-dimethylcarbamate
xref: CHEMBL521589
synonym: Bambec®
synonym: Oxeol®
approved: t
ligand name: bambuterol
type: SyntheticOrganicLigand

BW284C51
canonical SMILES: C=CC[N+](c1ccc(cc1)CCC(=O)CCc1ccc(cc1)[N+](CC=C)(C)C)(C)C
isomeric SMILES: C=CC[N+](c1ccc(cc1)CCC(=O)CCc1ccc(cc1)[N+](CC=C)(C)C)(C)C
in ch i key: ZAEXMNKDGJNLTA-UHFFFAOYSA-N
in ch i: InChI=1S/C27H38N2O/c1-7-21-28(3,4)25-15-9-23(10-16-25)13-19-27(30)20-14-24-11-17-26(18-12-24)29(5,6)22-8-2/h7-12,15-18H,1-2,13-14,19-22H2,3-6H3/q+2
iupac name: [4-[5-[4-(dimethyl-prop-2-enylazaniumyl)phenyl]-3-oxopentyl]phenyl]-dimethyl-prop-2-enylazanium
xref: CHEMBL140020
approved: f
ligand name: BW284C51
type: SyntheticOrganicLigand

donepezil
in ch i key: ADEBPBSSDYVVLD-UHFFFAOYSA-N
in ch i: InChI=1S/C24H29NO3/c1-27-22-14-19-13-20(24(26)21(19)15-23(22)28-2)12-17-8-10-25(11-9-17)16-18-6-4-3-5-7-18/h3-7,14-15,17,20H,8-13,16H2,1-2H3
comment: May be refered to as donepezil hydrochloride (PubChem CID 5741). In addition to the original brand, Aricept, generic donepezil formulations are now approved by the US FDA.
iupac name: 5,6-dimethoxy-2-[[1-(phenylmethyl)piperidin-4-yl]methyl]-2,3-dihydroinden-1-one
xref: CHEMBL502
synonym: Aricept®
synonym: E-2020
synonym: Donep
approved: t
ligand name: donepezil
type: SyntheticOrganicLigand

physostigmine
canonical SMILES: CNC(=O)Oc1ccc2c(c1)C1(C)CCN(C1N2C)C
in ch i key: PIJVFDBKTWXHHD-HIFRSBDPSA-N
in ch i: InChI=1S/C15H21N3O2/c1-15-7-8-17(3)13(15)18(4)12-6-5-10(9-11(12)15)20-14(19)16-2/h5-6,9,13H,7-8H2,1-4H3,(H,16,19)/t13-,15+/m1/s1
comment: Physostigmine, originally isolated from the Calabar bean, is a parasympathomimetic alkaloid, acting as a reversible cholinesterase inhibitor (the enzyme responsible for the breakdown of acetylcholine in the synaptic cleft of the neuromuscular junction).
iupac name: [(3aR,8bS)-3,4,8b-trimethyl-2,3a-dihydro-1H-pyrrolo[2,3-b]indol-7-yl] N-methylcarbamate
xref: CHEMBL94
synonym: Esromiotin
synonym: Ezerin
synonym: Fysostigmin
synonym: Physostol
synonym: Antilirium®
synonym: physostigmine salicylate
synonym: eserine
approved: t
ligand name: physostigmine
type: NaturalProductLigand

riboflavin
in ch i key: AUNGANRZJHBGPY-SCRDCRAPSA-N
in ch i: InChI=1S/C17H20N4O6/c1-7-3-9-10(4-8(7)2)21(5-11(23)14(25)12(24)6-22)15-13(18-9)16(26)20-17(27)19-15/h3-4,11-12,14,22-25H,5-6H2,1-2H3,(H,20,26,27)/t11-,12+,14-/m0/s1
comment: Riboflavin (vitamin B2) is a water-soluble vitamin that is required for the biosynthesis of flavin-derived enzyme cofactors that are essential for cellular respiration. Taken as a dietary supplement to combat vitamin B2 deficiency.
iupac name: 7,8-dimethyl-10-[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]benzo[g]pteridine-2,4-dione
xref: CHEMBL1534
approved: f
ligand name: riboflavin
type: MetaboliteLigand

cilengitide
in ch i key: AMLYAMJWYAIXIA-VWNVYAMZSA-N
in ch i: InChI=1S/C27H40N8O7/c1-15(2)22-25(41)33-17(10-7-11-30-27(28)29)23(39)31-14-20(36)32-18(13-21(37)38)24(40)34-19(26(42)35(22)3)12-16-8-5-4-6-9-16/h4-6,8-9,15,17-19,22H,7,10-14H2,1-3H3,(H,31,39)(H,32,36)(H,33,41)(H,34,40)(H,37,38)(H4,28,29,30)/t17-,18-,19+,22-/m0/s1
comment: Cilengitide is a cyclic RGD pentapeptide, first-in-class integrin inhibitor. It inhibits integrin αv-induced angiogenesis. It was investigated for anti-tumour activity. Glioblastoma was one of the cancers investigated <Reference id=31446/>, based on encouraging preclinical studies in animals <Reference id=31441/><Reference id=31444/><Reference id=31445/>.
iupac name: 2-[(2S,5R,8S,11S)-11-[3-(diaminomethylideneamino)propyl]-7-methyl-3,6,9,12,15-pentaoxo-5-(phenylmethyl)-8-propan-2-yl-1,4,7,10,13-pentazacyclopentadec-2-yl]acetic acid
xref: CHEMBL429876
synonym: EMD-12192
synonym: EMD-121974
approved: f
ligand name: cilengitide
type: PeptideLigand

P11
in ch i key: MBZSEGOTVVCKNO-KESUXUJOSA-N
in ch i: InChI=1S/C30H47N11O10/c1-15(2)24(29(49)39-20(8-17-11-34-14-36-17)26(46)37-19(30(50)51)5-3-4-6-31)41-27(47)21(9-23(43)44)38-28(48)22(12-42)40-25(45)18(32)7-16-10-33-13-35-16/h10-11,13-15,18-22,24,42H,3-9,12,31-32H2,1-2H3,(H,33,35)(H,34,36)(H,37,46)(H,38,48)(H,39,49)(H,40,45)(H,41,47)(H,43,44)(H,50,51)/t18-,19-,20-,21-,22-,24-/m0/s1
comment: Potent antagonist of the integrin αVβ3-vitronectin interaction with antiangiogenic action.
approved: f
ligand name: P11
type: PeptideLigand

A286982
isomeric SMILES: O=C(N1CCN(CC1)C(=O)C)/C=C/c1ccc(c(c1)N(=O)=O)Sc1ccccc1C(C)C
in ch i key: HTGGAYLWTDOFDK-PKNBQFBNSA-N
in ch i: InChI=1S/C24H27N3O4S/c1-17(2)20-6-4-5-7-22(20)32-23-10-8-19(16-21(23)27(30)31)9-11-24(29)26-14-12-25(13-15-26)18(3)28/h4-11,16-17H,12-15H2,1-3H3/b11-9+
comment: Potent inhibitor of the LFA-1/ICAM-1 interaction <Reference id=22418/>. LFA-1 (leukocyte function-associated antigen-1) is a beta2-integrin, and ICAM-1 (CD54) is an endothelial cell adhesion molecule.
iupac name: (E)-1-(4-acetylpiperazin-1-yl)-3-[3-nitro-4-(2-propan-2-ylphenyl)sulfanylphenyl]prop-2-en-1-one
xref: CHEMBL19677
synonym: A-286982
synonym: A 286982
approved: f
ligand name: A286982
type: SyntheticOrganicLigand

TCS2314
in ch i key: ITXAAOWFOURIHK-DEOSSOPVSA-N
in ch i: InChI=1S/C28H34N4O6/c1-19-4-2-3-5-23(19)30-28(37)29-22-8-6-20(7-9-22)16-25(33)32-14-15-38-18-24(32)27(36)31-12-10-21(11-13-31)17-26(34)35/h2-9,21,24H,10-18H2,1H3,(H,34,35)(H2,29,30,37)/t24-/m0/s1
iupac name: 2-[1-[(3S)-4-[2-[4-[(2-methylphenyl)carbamoylamino]phenyl]acetyl]morpholine-3-carbonyl]piperidin-4-yl]acetic acid
xref: CHEMBL389946
synonym: TCS-2314
synonym: TCS 2314
approved: f
ligand name: TCS2314
type: SyntheticOrganicLigand

BIO1211
in ch i key: NVVGCQABIHSJSQ-KFZSMJGVSA-N
in ch i: InChI=1S/C36H48N6O9/c1-20(2)17-26(38-29(43)18-23-12-14-24(15-13-23)37-36(51)40-25-10-7-6-9-22(25)5)32(46)39-27(19-30(44)45)33(47)41-31(21(3)4)34(48)42-16-8-11-28(42)35(49)50/h6-7,9-10,12-15,20-21,26-28,31H,8,11,16-19H2,1-5H3,(H,38,43)(H,39,46)(H,41,47)(H,44,45)(H,49,50)(H2,37,40,51)/t26-,27-,28-,31-/m0/s1
xref: CHEMBL88478
synonym: BIO-1211
synonym: BIO 1211
approved: f
ligand name: BIO1211
type: PeptideLigand

G4120
in ch i key: BIEZITROCMXFHL-QAETUUGQSA-N
in ch i: InChI=1S/C24H36N8O9S/c25-14(8-12-3-5-13(33)6-4-12)20(37)31-15(2-1-7-28-24(26)27)21(38)29-10-18(34)30-16(9-19(35)36)22(39)32-17(11-42)23(40)41/h3-6,14-17,33,42H,1-2,7-11,25H2,(H,29,38)(H,30,34)(H,31,37)(H,32,39)(H,35,36)(H,40,41)(H4,26,27,28)/t14-,15-,16-,17-/m0/s1
comment: G4120 is a synthetic Arg-Gly-Asp (RGD) containing peptide which potently inhibits platelet aggregation by antagonising fibrinogen binding to integrin αIIbβ3.
synonym: G 4120
synonym: G-4120
synonym: cyclic Arg-Gly-Asp-containing pentapeptide
synonym: L-cysteine, N-(mercaptoacetyl)-D-tyrosyl-L-arginylglycyl-L-alpha- aspartyl-cyclic(1-->5)-sulfide, 5-oxide
synonym: cyclic RGD
approved: f
ligand name: G4120
type: PeptideLigand

GR 144053
in ch i key: QGEGSJUSWLLZLH-UHFFFAOYSA-N
in ch i: InChI=1S/C18H27N5O2/c19-18(20)14-1-3-15(4-2-14)22-9-11-23(12-10-22)16-5-7-21(8-6-16)13-17(24)25/h1-4,16H,5-13H2,(H3,19,20)(H,24,25)
comment: GR 144053 inhibits paltelet aggregation by binding to integrin αIIb/β3 <Reference id=30052/>, thereby preventing integrin binding to fibrinogen. The compound is orally actrive and long-acting. Note that we show the parent molecule here, but the trihydrochloride salt may be used experimentally.
iupac name: 2-[4-[4-(4-carbamimidoylphenyl)piperazin-1-yl]piperidin-1-yl]acetic acid
xref: CHEMBL36326
synonym: GR144053
synonym: GR-144053
synonym: GR 144053 trihydrochloride
approved: f
ligand name: GR 144053
type: SyntheticOrganicLigand

tirofiban
in ch i key: COKMIXFXJJXBQG-NRFANRHFSA-N
in ch i: InChI=1S/C22H36N2O5S/c1-2-3-16-30(27,28)24-21(22(25)26)17-19-7-9-20(10-8-19)29-15-5-4-6-18-11-13-23-14-12-18/h7-10,18,21,23-24H,2-6,11-17H2,1H3,(H,25,26)/t21-/m0/s1
comment: Tirofiban is a rapidly-active but short-acting glycoprotein IIb/IIIa inhibitor type antiplatelet drug.
iupac name: (2S)-2-(butylsulfonylamino)-3-[4-(4-piperidin-4-ylbutoxy)phenyl]propanoic acid
xref: CHEMBL916
synonym: AGG
synonym: Aggrastat®
synonym: L-700462
synonym: MK-383
synonym: tirofiban hydrochloride (monohydrate)
approved: t
ligand name: tirofiban
type: SyntheticOrganicLigand

eptifibatide
in ch i key: CZKPOZZJODAYPZ-LROMGURASA-N
comment: Eptifibatide is a synthetic cyclic hexapeptide inhibitor of the integrin αIIbβ3 protein complex.
iupac name: 2-[(3R,11S,17S,20S,25aS)-11-(4-carbamimidamidobutyl)-3-carbamoyl-20-(indol-3-ylmethyl)-1,9,12,15,18,21-hexaoxo-docosahydro-1H-pyrrolo[2,1-g]1,2-dithia-5,8,11,14,17,20-hexaazacyclotricosan-17-yl]acetic acid
xref: CHEMBL1174
synonym: Eptifibatide Accord (generic)
synonym: C68-22
synonym: Integrelin®
synonym: Intrifiban
approved: t
ligand name: eptifibatide
type: SyntheticOrganicLigand

TCI15
in ch i key: XKLHCUGVLCGKKX-OALUTQOASA-N
in ch i: InChI=1S/C23H28N4O6S2/c1-23(2)19(27(15-34-23)35(32,33)17-11-7-4-8-12-17)20(28)26-18(21(29)30)14-25-22(31)24-13-16-9-5-3-6-10-16/h3-12,18-19H,13-15H2,1-2H3,(H,26,28)(H,29,30)(H2,24,25,31)/t18-,19-/m0/s1
iupac name: (2S)-2-{[(4S)-3-(benzenesulfonyl)-5,5-dimethyl-1,3-thiazolidin-4-yl]formamido}-3-[(benzylcarbamoyl)amino]propanoic acid
approved: f
ligand name: TCI15
type: SyntheticOrganicLigand

GRI977143
in ch i key: IYUOFUODBWFCBK-UHFFFAOYSA-N
in ch i: InChI=1S/C22H17NO3S/c24-14-16-6-1-2-11-19(16)27-13-5-12-23-21(25)17-9-3-7-15-8-4-10-18(20(15)17)22(23)26/h1-4,6-11,14H,5,12-13H2
iupac name: 2-[3-(1,3-dioxobenzo[de]isoquinolin-2-yl)propylsulfanyl]benzaldehyde
synonym: GRI-977143
approved: f
ligand name: GRI977143
type: SyntheticOrganicLigand

H2L5186303
in ch i key: BFNFDDZOFCRJTI-PORYWJCVSA-N
in ch i: InChI=1S/C26H20N2O6/c29-16-2-6-25(31)27-19-8-12-21(13-9-19)33-23-4-1-5-24(18-23)34-22-14-10-20(11-15-22)28-26(32)7-3-17-30/h1-18H,(H,27,31)(H,28,32)/b6-2-,7-3-
comment: H2L5186303 is a potent and selective LPA2 receptor antagonist <Reference id=23683/>.
iupac name: (Z)-4-oxo-N-[4-[3-[4-[[(Z)-4-oxobut-2-enoyl]amino]phenoxy]phenoxy]phenyl]but-2-enamide
synonym: compound 4 [PMID: 19800804]
approved: f
ligand name: H2L5186303
type: SyntheticOrganicLigand

CID16020046
in ch i key: VGUQVYZXABOXCX-UHFFFAOYSA-N
in ch i: InChI=1S/C25H19N3O4/c1-14-5-7-15(8-6-14)21-20-22(27-26-21)24(30)28(18-11-9-16(10-12-18)25(31)32)23(20)17-3-2-4-19(29)13-17/h2-13,23,29H,1H3,(H,26,27)(H,31,32)
iupac name: 4-[4-(3-hydroxyphenyl)-3-(4-methylphenyl)-6-oxo-1,4-dihydropyrrolo[3,4-d]pyrazol-5-yl]benzoic acid
xref: CHEMBL1341792
synonym: CID 16020046
approved: f
ligand name: CID16020046
type: SyntheticOrganicLigand

spiraprilat
in ch i key: FMMDBLMCSDRUPA-BPUTZDHNSA-N
in ch i: InChI=1S/C20H26N2O5S2/c1-13(21-15(18(24)25)8-7-14-5-3-2-4-6-14)17(23)22-12-20(28-9-10-29-20)11-16(22)19(26)27/h2-6,13,15-16,21H,7-12H2,1H3,(H,24,25)(H,26,27)/t13-,15-,16-/m0/s1
comment: ACE inhibitor drug metobolically generated from spirapril prodrug
iupac name: (7S)-8-[(2S)-2-[[(2S)-1-hydroxy-1-oxo-4-phenylbutan-2-yl]amino]propanoyl]-1,4-dithia-8-azaspiro[4.4]nonane-7-carboxylic acid
xref: CHEMBL579
synonym: SCH-33861
approved: t
ligand name: spiraprilat
type: SyntheticOrganicLigand

spirapril
in ch i key: HRWCVUIFMSZDJS-SZMVWBNQSA-N
in ch i: InChI=1S/C22H30N2O5S2/c1-3-29-21(28)17(10-9-16-7-5-4-6-8-16)23-15(2)19(25)24-14-22(30-11-12-31-22)13-18(24)20(26)27/h4-8,15,17-18,23H,3,9-14H2,1-2H3,(H,26,27)/t15-,17-,18-/m0/s1
comment: ACE inhibitor prodrug metabolised to spiraprilat
iupac name: (7S)-8-[(2S)-2-[[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino]propanoyl]-1,4-dithia-8-azaspiro[4.4]nonane-7-carboxylic acid
xref: CHEMBL431
synonym: SCH-33844
synonym: Renormax®
approved: t
ligand name: spirapril
type: SyntheticOrganicLigand

moexiprilat
in ch i key: CMPAGYDKASJORH-YSSFQJQWSA-N
in ch i: InChI=1S/C25H30N2O7/c1-15(26-19(24(29)30)10-9-16-7-5-4-6-8-16)23(28)27-14-18-13-22(34-3)21(33-2)12-17(18)11-20(27)25(31)32/h4-8,12-13,15,19-20,26H,9-11,14H2,1-3H3,(H,29,30)(H,31,32)/t15-,19-,20-/m0/s1
comment: Moexiprilat is the in vivo formed, active form of the prodrug moexipril. Moexiprilat is an ACE inhibitor.
iupac name: (3S)-2-[(2S)-2-[[(2S)-1-hydroxy-1-oxo-4-phenylbutan-2-yl]amino]propanoyl]-6,7-dimethoxy-3,4-dihydro-1H-isoquinoline-3-carboxylic acid
xref: CHEMBL1201405
synonym: RS-10029
approved: t
ligand name: moexiprilat
type: SyntheticOrganicLigand

moexipril
in ch i key: UWWDHYUMIORJTA-HSQYWUDLSA-N
in ch i: InChI=1S/C27H34N2O7/c1-5-36-27(33)21(12-11-18-9-7-6-8-10-18)28-17(2)25(30)29-16-20-15-24(35-4)23(34-3)14-19(20)13-22(29)26(31)32/h6-10,14-15,17,21-22,28H,5,11-13,16H2,1-4H3,(H,31,32)/t17-,21-,22-/m0/s1
comment: ACE inhibitor prodrug metabolised to moexiprilat. This compound has hydrochloride database entries such as CID 54889 and nine isomers in PubChem.
iupac name: (3S)-2-[(2S)-2-[[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino]propanoyl]-6,7-dimethoxy-3,4-dihydro-1H-isoquinoline-3-carboxylic acid
xref: CHEMBL1165
synonym: RS-10085
synonym: SPM-925
synonym: Univasc®
approved: t
ligand name: moexipril
type: SyntheticOrganicLigand

aprotinin
in ch i key: ZPNFWUPYTFPOJU-LPYSRVMUSA-N
comment: 58 amino-acid residue inhibitor of plasmin and other proteolytic enzymes.
synonym: Trasylol®
synonym: pancreatic trypsin inhibitor
synonym: BPTI
synonym: basic protease inhibitor (BPI)
approved: t
ligand name: aprotinin
type: PeptideLigand

sulforaphane
canonical SMILES: S=C=NCCCCS(=O)C
isomeric SMILES: S=C=NCCCCS(=O)C
in ch i key: SUVMJBTUFCVSAD-UHFFFAOYSA-N
in ch i: InChI=1S/C6H11NOS2/c1-10(8)5-3-2-4-7-6-9/h2-5H2,1H3
comment: Found in cruciferous vegetables such as brocolli. It has potential chemopreventive <Reference id=30770/>, anti-cancer <Reference id=30768/> and neuroprotective actions <Reference id=30769/>. It may act as a quinone reductase inducer <Reference id=30771/>.
iupac name: 1-isothiocyanato-4-methylsulfinylbutane
approved: f
ligand name: sulforaphane
type: NaturalProductLigand

compound 20 [PMID: 22153340]
in ch i key: LLJREHOWNIBILL-NRFANRHFSA-N
in ch i: InChI=1S/C22H21NO6S/c1-12(2)21(22(24)25)23-30(26,27)15-6-7-16-17-10-14(18-8-4-13(3)28-18)5-9-19(17)29-20(16)11-15/h4-12,21,23H,1-3H3,(H,24,25)/t21-/m0/s1
iupac name: (2S)-3-methyl-2-[12-(5-methylfuran-2-yl)-8-oxatricyclo[7.4.0.02,7]trideca-1(9),2(7),3,5,10,12-hexaene-5-sulfonamido]butanoic acid
xref: CHEMBL1935285
approved: f
ligand name: compound 20 [PMID: 22153340]
type: SyntheticOrganicLigand

compound 2 [PMID: 8410973]
in ch i key: SXQPECMJHHMDFO-DUGYJJFCSA-N
comment: Cathepsin E inhbitor
iupac name: (2S)-N-[(2S,3R)-1-cyclohexyl-4,4-difluoro-3-hydroxy-4-{[(2S)-2-methylbutyl]carbamoyl}butan-2-yl]-2-[(2S)-2-[(morpholine-4-sulfonyl)amino]-3-phenylpropanamido]pent-4-enamide
xref: CHEMBL313773
approved: f
ligand name: compound 2 [PMID: 8410973]
type: SyntheticOrganicLigand

S 17092
in ch i key: NXSXRIHXEQSYEZ-KNJMJIDISA-N
in ch i: InChI=1S/C22H28N2O2S/c25-21(18-13-17(18)15-6-2-1-3-7-15)24-19-9-5-4-8-16(19)12-20(24)22(26)23-10-11-27-14-23/h1-3,6-7,16-20H,4-5,8-14H2/t16-,17-,18+,19-,20-/m0/s1
comment: Prolyl peptidase inhibitor
iupac name: [(2S,3aS,7aS)-2-(1,3-thiazolidine-3-carbonyl)-2,3,3a,4,5,6,7,7a-octahydroindol-1-yl]-[(1R,2R)-2-phenylcyclopropyl]methanone
xref: CHEMBL1086968
synonym: S17092
synonym: S-17092
approved: f
ligand name: S 17092
type: SyntheticOrganicLigand

phenylacetyl-Arg-Val-Arg-4-amidinobenzylamide
in ch i key: YGMAIAXBJLVVLI-KLJDGLGGSA-N
in ch i: InChI=1S/C33H50N12O4/c1-20(2)27(45-30(48)25(11-7-17-41-33(38)39)43-26(46)18-21-8-4-3-5-9-21)31(49)44-24(10-6-16-40-32(36)37)29(47)42-19-22-12-14-23(15-13-22)28(34)35/h3-5,8-9,12-15,20,24-25,27H,6-7,10-11,16-19H2,1-2H3,(H3,34,35)(H,42,47)(H,43,46)(H,44,49)(H,45,48)(H4,36,37,40)(H4,38,39,41)/t24-,25-,27-/m0/s1
comment: This compound is an inhibitor of furin and furin-like proprotein convertases <Reference id=22351/>.
iupac name: (2S)-N-[(4-carbamimidoylphenyl)methyl]-5-[(diaminomethylidene)amino]-2-[(2S)-2-[(2S)-5-[(diaminomethylidene)amino]-2-(2-phenylacetamido)pentanamido]-3-methylbutanamido]pentanamide
xref: CHEMBL566340
synonym: compound 15 [PMID:20038105]
approved: f
ligand name: phenylacetyl-Arg-Val-Arg-4-amidinobenzylamide
type: SyntheticOrganicLigand

BOMA
canonical SMILES: N#CCc1ccc(cc1OC)c1nc2c(o1)cccc2
isomeric SMILES: N#CCc1ccc(cc1OC)c1nc2c(o1)cccc2
in ch i key: LWSOZPNJUFEDJU-UHFFFAOYSA-N
in ch i: InChI=1S/C16H12N2O2/c1-19-15-10-12(7-6-11(15)8-9-17)16-18-13-4-2-3-5-14(13)20-16/h2-7,10H,8H2,1H3
iupac name: 2-[4-(1,3-benzoxazol-2-yl)-2-methoxyphenyl]acetonitrile
approved: f
ligand name: BOMA
type: SyntheticOrganicLigand

(S)-EF-1520
in ch i key: CUESOMOCKVRNIW-KRWDZBQOSA-N
in ch i: InChI=1S/C22H26N2O2S2/c1-14-9-12-27-20(14)16(21-15(2)10-13-28-21)6-5-11-24(3)17-7-4-8-18-19(17)22(25)23-26-18/h6,9-10,12-13,17H,4-5,7-8,11H2,1-3H3,(H,23,25)/t17-/m0/s1
iupac name: (4S)-4-{[4,4-bis(3-methylthiophen-2-yl)but-3-en-1-yl](methyl)amino}-4,5,6,7-tetrahydro-1,2-benzoxazol-3-ol
xref: CHEMBL1628534
approved: f
ligand name: (S)-EF-1520
type: SyntheticOrganicLigand

JNJ-10311795
in ch i key: XUJQPDQURBZEGJ-UHFFFAOYSA-N
in ch i: InChI=1S/C40H35N2O6P/c1-41(32-19-21-42(22-20-32)39(44)31-18-17-26-9-2-3-11-28(26)23-31)40(45)36-25-30-13-5-4-12-29(30)24-35(36)37(43)38(49(46,47)48)34-16-8-14-27-10-6-7-15-33(27)34/h2-18,23-25,32,38H,19-22H2,1H3,(H2,46,47,48)
comment: JNJ-10311795 is a chymase inhibitor with cathepsin G cross-reactivity. The isomer in CID 656932 is contained in PDB X-ray crystal structures <Reference id=33068/>. It is suggested to have potential clinical utility in pulmonary inflammatory diseases such as asthma and COPD.
iupac name: [2-[3-[methyl-[1-(naphthalene-2-carbonyl)piperidin-4-yl]carbamoyl]naphthalen-2-yl]-1-naphthalen-1-yl-2-oxoethyl]phosphonic acid
xref: CHEMBL374027
approved: f
ligand name: JNJ-10311795
type: SyntheticOrganicLigand

compound 22 [PMID: 19899765]
in ch i key: WWTBZEKOSBFBEM-SPWPXUSOSA-N
in ch i: InChI=1S/C37H38N3O7P/c41-35(39-33(36(42)43)22-29-23-38-32-19-11-10-18-31(29)32)30(20-26-12-4-1-5-13-26)25-48(45,46)34(21-27-14-6-2-7-15-27)40-37(44)47-24-28-16-8-3-9-17-28/h1-19,23,30,33-34,38H,20-22,24-25H2,(H,39,41)(H,40,44)(H,42,43)(H,45,46)/t30?,33-,34+/m0/s1
comment: ECE1 inhibitor
iupac name: (2S)-2-(2-benzyl-3-{[(1R)-1-{[(benzyloxy)carbonyl]amino}-2-phenylethyl](hydroxy)phosphoryl}propanamido)-3-(1H-indol-3-yl)propanoic acid
xref: CHEMBL571153
approved: f
ligand name: compound 22 [PMID: 19899765]
type: SyntheticOrganicLigand

PSB-0788
in ch i key: JQZJACVYMPKVDS-UHFFFAOYSA-N
iupac name: 8-(4-{4-[(4-chlorophenyl)methyl]piperazine-1-sulfonyl}phenyl)-1-propyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione
xref: CHEMBL482436
synonym: PSB0788
synonym: PSB 0788
approved: f
ligand name: PSB-0788
type: SyntheticOrganicLigand

5-Cl-5-deoxy-(±)-ENBA
in ch i key: PVJGDYDNVNCGBT-UHFFFAOYSA-N
in ch i: InChI=1S/C17H22ClN5O3/c18-5-11-13(24)14(25)17(26-11)23-7-21-12-15(19-6-20-16(12)23)22-10-4-8-1-2-9(10)3-8/h6-11,13-14,17,24-25H,1-5H2,(H,19,20,22)
iupac name: 2-[6-({bicyclo[2.2.1]heptan-2-yl}amino)-9H-purin-9-yl]-5-(chloromethyl)oxolane-3,4-diol
approved: f
ligand name: 5-Cl-5-deoxy-(±)-ENBA
type: SyntheticOrganicLigand

BC11-38
canonical SMILES: CCCSc1nc2CCSc2c(=O)n1c1ccccc1
isomeric SMILES: CCCSc1nc2CCSc2c(=O)n1c1ccccc1
in ch i key: YHNDCCKFNWDQGW-UHFFFAOYSA-N
in ch i: InChI=1S/C15H16N2OS2/c1-2-9-20-15-16-12-8-10-19-13(12)14(18)17(15)11-6-4-3-5-7-11/h3-7H,2,8-10H2,1H3
iupac name: 3-phenyl-2-(propylsulfanyl)-3H,4H,6H,7H-thieno[3,2-d]pyrimidin-4-one
approved: f
ligand name: BC11-38
type: SyntheticOrganicLigand

gisadenafil
in ch i key: YPFZMBHKIVDSNR-UHFFFAOYSA-N
in ch i: InChI=1S/C23H33N7O5S/c1-5-18-19-20(27-30(18)12-13-34-4)22(31)26-21(25-19)17-14-16(15-24-23(17)35-7-3)36(32,33)29-10-8-28(6-2)9-11-29/h14-15H,5-13H2,1-4H3,(H,25,26,31)
iupac name: 5-[2-ethoxy-5-(4-ethylpiperazin-1-yl)sulfonylpyridin-3-yl]-3-ethyl-2-(2-methoxyethyl)-4H-pyrazolo[3,4-e]pyrimidin-7-one
xref: CHEMBL1928262
synonym: UK 369003
synonym: UK-369003
approved: f
ligand name: gisadenafil
type: SyntheticOrganicLigand

RS-25344
in ch i key: YLHRMVRLIOIWTO-UHFFFAOYSA-N
in ch i: InChI=1S/C19H13N5O4/c25-18-16-5-2-8-21-17(16)23(14-3-1-4-15(11-14)24(27)28)19(26)22(18)12-13-6-9-20-10-7-13/h1-11H,12H2
iupac name: 1-(3-nitrophenyl)-3-(pyridin-4-ylmethyl)pyrido[3,2-e]pyrimidine-2,4-dione
xref: CHEMBL1232082
synonym: RS 25344
approved: f
ligand name: RS-25344
type: SyntheticOrganicLigand

HJC 0350
canonical SMILES: Cc1cc(C)c(c(c1)C)S(=O)(=O)n1cc(cc1C)C
isomeric SMILES: Cc1cc(C)c(c(c1)C)S(=O)(=O)n1cc(cc1C)C
in ch i key: AFZWZVLPIMHLSE-UHFFFAOYSA-N
in ch i: InChI=1S/C15H19NO2S/c1-10-6-12(3)15(13(4)7-10)19(17,18)16-9-11(2)8-14(16)5/h6-9H,1-5H3
iupac name: 2,4-dimethyl-1-(2,4,6-trimethylphenyl)sulfonylpyrrole
xref: CHEMBL2313646
synonym: HJC0350
approved: f
ligand name: HJC 0350
type: SyntheticOrganicLigand

compound 28 [PMID: 18324760]
in ch i key: DGMLSHVZZKUDPN-AABGKKOBSA-N
in ch i: InChI=1S/C22H33N2O6P/c1-15(2)12-19(23-16(3)25)21(26)24-11-7-10-20(24)31(29,30)14-18(22(27)28)13-17-8-5-4-6-9-17/h4-6,8-9,15,18-20H,7,10-14H2,1-3H3,(H,23,25)(H,27,28)(H,29,30)/t18-,19+,20+/m1/s1
comment: ACE2 inhibitor
iupac name: (2S)-2-benzyl-3-{[(2S)-1-[(2S)-2-acetamido-4-methylpentanoyl]pyrrolidin-2-yl](hydroxy)phosphoryl}propanoic acid
xref: CHEMBL260273
approved: f
ligand name: compound 28 [PMID: 18324760]
type: SyntheticOrganicLigand

NS 2028
canonical SMILES: Brc1ccc2c(c1)n1c(CO2)noc1=O
isomeric SMILES: Brc1ccc2c(c1)n1c(CO2)noc1=O
in ch i key: MUDRLQRJCGJJTB-UHFFFAOYSA-N
in ch i: InChI=1S/C9H5BrN2O3/c10-5-1-2-7-6(3-5)12-8(4-14-7)11-15-9(12)13/h1-3H,4H2
iupac name: 8-bromo-4H-[1,2,4]oxadiazolo[3,4-c][1,4]benzoxazin-1-one
xref: CHEMBL507122
synonym: NS-2028
synonym: NS2028
approved: f
ligand name: NS 2028
type: SyntheticOrganicLigand

methyl 5-[(4-tert-butylbenzoyl)amino]-2H-1,2,4-triazole-3-carboxylate
in ch i key: LVKKWCOINMSBPK-UHFFFAOYSA-N
in ch i: InChI=1S/C15H18N4O3/c1-15(2,3)10-7-5-9(6-8-10)12(20)17-14-16-11(18-19-14)13(21)22-4/h5-8H,1-4H3,(H2,16,17,18,19,20)
comment: Factor 12 inhibitor
iupac name: methyl 5-[(4-tert-butylbenzoyl)amino]-2H-1,2,4-triazole-3-carboxylate
xref: CHEMBL1595992
approved: f
ligand name: methyl 5-[(4-tert-butylbenzoyl)amino]-2H-1,2,4-triazole-3-carboxylate
type: SyntheticOrganicLigand

compound 1 [PMID: 16650987]
isomeric SMILES: NC(=O)NCc1ccc(c(c1)C1=CC(=C/C(=c/2/[nH]c3c([nH]2)ccc(c3)C(=N)N)/C1=O)C(C(=O)O)CC(=O)O)O
in ch i key: VPCHMCAFZYYMSK-JJIBRWJFSA-N
in ch i: InChI=1S/C26H24N6O7/c27-23(28)12-2-3-18-19(8-12)32-24(31-18)17-7-13(14(25(37)38)9-21(34)35)6-16(22(17)36)15-5-11(1-4-20(15)33)10-30-26(29)39/h1-8,14,31-33H,9-10H2,(H3,27,28)(H,34,35)(H,37,38)(H3,29,30,39)/b24-17+
comment: Factor 7 inhibitor. This compound is represented on ChEMBL without specified stereochemsitry by the entry CHEMBL206387.
iupac name: 2-[3-(5-carbamimidoyl-2,3-dihydro-1H-1,3-benzodiazol-2-ylidene)-5-{5-[(carbamoylamino)methyl]-2-hydroxyphenyl}-4-oxocyclohexa-1,5-dien-1-yl]butanedioic acid
approved: f
ligand name: compound 1 [PMID: 16650987]
type: SyntheticOrganicLigand

(S)-2,3-epoxysqualene
isomeric SMILES: C/C(=C/CC/C=C(/CC/C=C(/CC[C@@H]1OC1(C)C)/C)/C)/CC/C=C(/CCC=C(C)C)/C
in ch i key: QYIMSPSDBYKPPY-RSKUXYSASA-N
in ch i: InChI=1S/C30H50O/c1-24(2)14-11-17-27(5)20-12-18-25(3)15-9-10-16-26(4)19-13-21-28(6)22-23-29-30(7,8)31-29/h14-16,20-21,29H,9-13,17-19,22-23H2,1-8H3/b25-15+,26-16+,27-20+,28-21+/t29-/m0/s1
iupac name: (3S)-2,2-dimethyl-3-[(7E)-3,7,12,16,20-pentamethylhenicosa-3,7,11,15,19-pentaenyl]oxirane
synonym: (S)-2,3-epoxysqualene
synonym: squalene 2,3-epoxide
approved: f
ligand name: (S)-2,3-epoxysqualene
type: MetaboliteLigand

compound 57 [PMID: 20121197]
in ch i key: QGLTXLFHFVMPJH-UHFFFAOYSA-N
in ch i: InChI=1S/C29H32N4O3S/c1-19(2)16-32-17-21-11-6-7-12-23(21)33-29(34)35-18-25(20-9-4-3-5-10-20)36-24-13-8-14-26-22(24)15-27(37-26)28(30)31/h3-15,19,25,32H,16-18H2,1-2H3,(H3,30,31)(H,33,34)
comment: Compound 57 [PMID: 20121197] <Reference id=22353/> is a potent inhibitor of the serine protease activity of blood clotting factor IXa. Factor IXa inhibition is a novel mechanism with the potential to provide alternative effective anticoagulants for clinical use <Reference id=33593/>.
iupac name: 2-[(2-carbamimidoyl-1-benzothiophen-4-yl)oxy]-2-phenylethyl N-(2-{[(2-methylpropyl)amino]methyl}phenyl)carbamate
xref: CHEMBL597557
approved: f
ligand name: compound 57 [PMID: 20121197]
type: SyntheticOrganicLigand

KGP94
canonical SMILES: NC(=S)NN=C(c1cccc(c1)Br)c1cccc(c1)O
isomeric SMILES: NC(=S)N/N=C(/c1cccc(c1)Br)/c1cccc(c1)O
in ch i key: ZDBKSZKTCPOBFR-LGMDPLHJSA-N
in ch i: InChI=1S/C14H12BrN3OS/c15-11-5-1-3-9(7-11)13(17-18-14(16)20)10-4-2-6-12(19)8-10/h1-8,19H,(H3,16,18,20)/b17-13-
comment: CATL inhibitor. The Z stereoisoform is represented by CID 25234575.
xref: CHEMBL1269632
approved: f
ligand name: KGP94
type: SyntheticOrganicLigand

α-methylserine-O-phosphate
canonical SMILES: OC(=O)C(COP(=O)(O)O)(N)C
isomeric SMILES: OC(=O)C(COP(=O)(O)O)(N)C
in ch i key: GSFCOAGADOGIGE-UHFFFAOYSA-N
in ch i: InChI=1S/C4H10NO6P/c1-4(5,3(6)7)2-11-12(8,9)10/h2,5H2,1H3,(H,6,7)(H2,8,9,10)
iupac name: 2-amino-2-methyl-3-phosphonooxypropanoic acid
xref: CHEMBL1437137
synonym: α-MSOP
approved: f
ligand name: α-methylserine-O-phosphate
type: SyntheticOrganicLigand

alpha-ketothiazole analogue 36
in ch i key: BGBJLVHKOHYLME-MNAPGUCWSA-N
comment: Factor 11 inhibitor
iupac name: (2S)-2-[[(1R)-1-(4-bromophenyl)ethyl]carbamoylamino]-5-(carbamoylamino)-N-[(2S)-1-[[(2S)-5-(diaminomethylideneamino)-1-oxo-1-(1,3-thiazol-2-yl)pentan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]pentanamide
xref: CHEMBL273653
approved: f
ligand name: alpha-ketothiazole analogue 36
type: SyntheticOrganicLigand

DG-051
in ch i key: PVCTYSQBVIGZRU-KRWDZBQOSA-N
in ch i: InChI=1S/C21H24ClNO4/c22-16-5-7-19(8-6-16)27-20-11-9-18(10-12-20)26-15-17-3-1-13-23(17)14-2-4-21(24)25/h5-12,17H,1-4,13-15H2,(H,24,25)/t17-/m0/s1
comment: Leukotriene 4 hydrolase inhbitor
iupac name: 4-[(2S)-2-[4-(4-chlorophenoxy)phenoxymethyl]pyrrolidin-1-yl]butanoic acid
xref: CHEMBL565789
synonym: compound 20 [PMID: 19950900]
approved: f
ligand name: DG-051
type: SyntheticOrganicLigand

compound 4 [PMID: 18163548]
in ch i key: ZNOKJHWJKULOGM-ZWKOTPCHSA-N
in ch i: InChI=1S/C21H27N5O6S/c22-19(23)16-8-6-14(7-9-16)10-24-20(29)17(11-27)25-21(30)18(12-28)26-33(31,32)13-15-4-2-1-3-5-15/h1-9,17-18,26-28H,10-13H2,(H3,22,23)(H,24,29)(H,25,30)/t17-,18+/m0/s1
comment: PLAU inhibitor. Analogue of clinical candidate WX-UK1.
iupac name: (2R)-N-[(2S)-1-[(4-carbamimidoylphenyl)methylamino]-3-hydroxy-1-oxopropan-2-yl]-3-hydroxy-2-(phenylmethylsulfonylamino)propanamide
xref: CHEMBL252937
approved: f
ligand name: compound 4 [PMID: 18163548]
type: SyntheticOrganicLigand

D-chiro-inositol
canonical SMILES: OC1C(O)C(O)C(C(C1O)O)O
in ch i key: CDAISMWEOUEBRE-LKPKBOIGSA-N
in ch i: InChI=1S/C6H12O6/c7-1-2(8)4(10)6(12)5(11)3(1)9/h1-12H/t1-,2-,3-,4-,5+,6+/m0/s1
comment: PubChem CID 892 shows the non-chiral inositol structure
iupac name: (1R,2R,3S,4S,5S,6S)-cyclohexane-1,2,3,4,5,6-hexol
xref: CHEMBL1231671
synonym: DCI
approved: f
ligand name: D-chiro-inositol
type: MetaboliteLigand

ONO-4817
in ch i key: HDWWQELUBWGQGA-WMZOPIPTSA-N
in ch i: InChI=1S/C22H28N2O6/c1-3-28-15-29-14-18(13-16(2)21(25)24-27)23-22(26)17-9-11-20(12-10-17)30-19-7-5-4-6-8-19/h4-12,16,18,27H,3,13-15H2,1-2H3,(H,23,26)(H,24,25)/t16-,18-/m0/s1
comment: MMP8 and MMP2 inhibitor. Alternative stereo forms can be found in PubChem.
iupac name: N-[(2S,4S)-1-(ethoxymethoxy)-5-(hydroxyamino)-4-methyl-5-oxopentan-2-yl]-4-(phenoxy)benzamide
synonym: ONO4817
synonym: ONO 4817
approved: f
ligand name: ONO-4817
type: SyntheticOrganicLigand

UK-356202
in ch i key: UXNWIRHZMHGOCE-UHFFFAOYSA-N
in ch i: InChI=1S/C17H13ClN4O2/c18-14-8-21-15(22-17(19)20)13-7-10(4-5-12(13)14)9-2-1-3-11(6-9)16(23)24/h1-8H,(H,23,24)(H4,19,20,21,22)
comment: Urokinase-type plasminogen activator inhibitor
iupac name: 3-[4-chloro-1-(diaminomethylideneamino)isoquinolin-7-yl]benzoic acid
xref: CHEMBL111576
synonym: UK-356,202
synonym: compound 13j [PMID: 15149680]
approved: f
ligand name: UK-356202
type: SyntheticOrganicLigand

compound 1 [PMID: 11425539]
canonical SMILES: O=C1N(Cc2ccccc2)C(=O)N1Cc1ccccc1
isomeric SMILES: O=C1N(Cc2ccccc2)C(=O)N1Cc1ccccc1
in ch i key: PGIXYPNBNAOYHW-UHFFFAOYSA-N
in ch i: InChI=1S/C16H14N2O2/c19-15-17(11-13-7-3-1-4-8-13)16(20)18(15)12-14-9-5-2-6-10-14/h1-10H,11-12H2
comment: Cathepsin G inhibitor
iupac name: 1,3-bis(phenylmethyl)-1,3-diazetidine-2,4-dione
xref: CHEMBL47394
approved: f
ligand name: compound 1 [PMID: 11425539]
type: SyntheticOrganicLigand

compound 1 [PMID: 10498202]
in ch i key: DQHKQRXAVNDAFY-UWXQCODUSA-N
comment: Cathepsin D inhibitor
iupac name: 2-bromo-N-[(2S,3S)-4-[2-(2,4-dichlorophenyl)ethyl-[3-(1,3-dioxoisoindol-2-yl)propanoyl]amino]-3-hydroxy-1-[3-(phenoxy)phenyl]butan-2-yl]-4,5-dimethoxybenzamide
xref: CHEMBL81927
approved: f
ligand name: compound 1 [PMID: 10498202]
type: SyntheticOrganicLigand

example 98 [WO2011020806]
in ch i key: RAFVKOLBEOKYJW-SFHVURJKSA-N
comment: BACE2 inhibitor from the patent WO2011020806 <Reference id=26477/>.
iupac name: N-{3-[(3R)-5-amino-3-methyl-3,6-dihydro-2H-1,4-oxazin-3-yl]-4-fluorophenyl}-5-chloro-3-methylpyridine-2-carboxamide
approved: f
ligand name: example 98 [WO2011020806]
type: SyntheticOrganicLigand

ST074946
canonical SMILES: N#Cc1c(N)n(nc2c1=CC(C)(C)OC2)c1ccccc1
isomeric SMILES: N#Cc1c(N)n(nc2c1=CC(C)(C)OC2)c1ccccc1
in ch i key: XQJQZTOXHGIQCA-UHFFFAOYSA-N
in ch i: InChI=1S/C16H16N4O/c1-16(2)8-12-13(9-17)15(18)20(19-14(12)10-21-16)11-6-4-3-5-7-11/h3-8H,10,18H2,1-2H3
comment: PubChem Confirmatory BioAssay for Sentrin-Specific Protease 8
iupac name: 3-amino-6,6-dimethyl-2-phenyl-8H-pyrano[4,5-e]pyridazine-4-carbonitrile
xref: CHEMBL171632
approved: f
ligand name: ST074946
type: SyntheticOrganicLigand

UAMC00039
canonical SMILES: NC(C(=O)N1CCCCC1)CCNCc1ccc(cc1)Cl
isomeric SMILES: N[C@H](C(=O)N1CCCCC1)CCNCc1ccc(cc1)Cl
in ch i key: DNVZYSMOLXCOLY-HNNXBMFYSA-N
in ch i: InChI=1S/C16H24ClN3O/c17-14-6-4-13(5-7-14)12-19-9-8-15(18)16(21)20-10-2-1-3-11-20/h4-7,15,19H,1-3,8-12,18H2/t15-/m0/s1
comment: DPP2 inhibitor as function probe
iupac name: (2S)-2-amino-4-[(4-chlorophenyl)methylamino]-1-piperidin-1-ylbutan-1-one
xref: CHEMBL98869
approved: f
ligand name: UAMC00039
type: SyntheticOrganicLigand

bis-triazole derivative 10
in ch i key: BKSCOHJNKDJECO-XZWHSSHBSA-N
in ch i: InChI=1S/C33H35N11O4S/c34-31(35)26-11-9-22(10-12-26)16-36-32(45)29-14-27-19-43(41-38-27)17-24-7-4-8-25(13-24)18-44-20-28(39-42-44)15-30(33(46)37-29)40-49(47,48)21-23-5-2-1-3-6-23/h1-13,19-20,29-30,40H,14-18,21H2,(H3,34,35)(H,36,45)(H,37,46)/t29-,30+/m0/s1
comment: Potent and selective plasmin inhibitor
xref: CHEMBL2016873
approved: f
ligand name: bis-triazole derivative 10
type: SyntheticOrganicLigand

compound 18 [PMID: 15664838]
in ch i key: ZKIQFLSGMMYCGS-UHFFFAOYSA-N
in ch i: InChI=1S/C29H30F2N4O2/c30-24-9-5-20(6-10-24)28(21-7-11-25(31)12-8-21)34-15-13-33(14-16-34)27(36)17-26(32)29(37)35-18-22-3-1-2-4-23(22)19-35/h1-12,26,28H,13-19,32H2
comment: This compound is a potent and selective inhibitor of dipeptidyl-peptidase 8 (DPP8) <Reference id=22324/>.
iupac name: 2-amino-4-[4-[bis(4-fluorophenyl)methyl]piperazin-1-yl]-1-(1,3-dihydroisoindol-2-yl)butane-1,4-dione
xref: CHEMBL367368
approved: f
ligand name: compound 18 [PMID: 15664838]
type: SyntheticOrganicLigand

compound (R)-26 [PMID: 22686657]
in ch i key: UGAZRSHSXNNYTK-HNNXBMFYSA-N
in ch i: InChI=1S/C17H24N4O4S/c1-13(2)10-26(24,25)11-15(17(23)21(4)20(3)12-18)19-16(22)14-8-6-5-7-9-14/h5-9,13,15H,10-11H2,1-4H3,(H,19,22)/t15-/m0/s1
comment: Potent selctive inhibitor of cathepsin S
iupac name: N-[(1R)-1-(N'-cyano-N,N'-dimethylhydrazinecarbonyl)-2-(2-methylpropanesulfonyl)ethyl]benzamide
xref: CHEMBL2153161
approved: f
ligand name: compound (R)-26 [PMID: 22686657]
type: SyntheticOrganicLigand

compound 1a [PMID: 15055993]
in ch i key: WLWNRAWQDZRXMB-YLFCFFPRSA-N
in ch i: InChI=1S/C18H20N2O8S/c21-14-10-20(15(18(24)19-25)17(23)16(14)22)29(26,27)13-8-6-12(7-9-13)28-11-4-2-1-3-5-11/h1-9,14-17,21-23,25H,10H2,(H,19,24)/t14-,15+,16+,17+/m0/s1
comment: Matrix metalloproteinase-9 inhibitor as potential antipsoriatic agent
iupac name: (2R,3R,4R,5S)-N,3,4,5-tetrahydroxy-1-[4-(phenoxy)phenyl]sulfonylpiperidine-2-carboxamide
xref: CHEMBL61193
approved: f
ligand name: compound 1a [PMID: 15055993]
type: SyntheticOrganicLigand

Z-Arg-Leu-Val-Agly-Ile-Val-OMe
in ch i key: ZLXFGUGFOLETFJ-POPCVQDUSA-N
in ch i: InChI=1S/C38H64N10O9/c1-10-24(8)30(33(51)45-29(23(6)7)35(53)56-9)46-37(54)48-47-34(52)28(22(4)5)44-32(50)27(19-21(2)3)42-31(49)26(17-14-18-41-36(39)40)43-38(55)57-20-25-15-12-11-13-16-25/h11-13,15-16,21-24,26-30H,10,14,17-20H2,1-9H3,(H,42,49)(H,43,55)(H,44,50)(H,45,51)(H,47,52)(H4,39,40,41)(H2,46,48,54)/t24-,26-,27-,28-,29-,30-/m0/s1
comment: Potent and selective inhibitor of cathepsin B
iupac name: methyl (2S)-2-[[(2S,3S)-2-[[[(2S)-2-[[(2S)-2-[[(2S)-5-(diaminomethylideneamino)-2-(phenylmethoxycarbonylamino)pentanoyl]amino]-4-methylpentanoyl]amino]-3-methylbutanoyl]amino]carbamoylamino]-3-methylpentanoyl]amino]-3-methylbutanoate
xref: CHEMBL2028907
approved: f
ligand name: Z-Arg-Leu-Val-Agly-Ile-Val-OMe
type: PeptideLigand

CAA0225
in ch i key: ZMZQYVMNDRBKLO-SDHOMARFSA-N
in ch i: InChI=1S/C28H29N3O5/c32-22-13-11-19(12-14-22)15-16-29-27(34)24-25(36-24)28(35)31-23(17-20-7-3-1-4-8-20)26(33)30-18-21-9-5-2-6-10-21/h1-14,23-25,32H,15-18H2,(H,29,34)(H,30,33)(H,31,35)/t23-,24-,25-/m0/s1
comment: Probe for autophagic proteolysis
iupac name: (2S,3S)-2-N-[(1S)-1-(benzylcarbamoyl)-2-phenylethyl]-3-N-[2-(4-hydroxyphenyl)ethyl]oxirane-2,3-dicarboxamide
approved: f
ligand name: CAA0225
type: SyntheticOrganicLigand

FTI 276
in ch i key: ZIXDDEATQSBHHL-BEFAXECRSA-N
in ch i: InChI=1S/C21H27N3O3S2/c1-29-10-9-19(21(26)27)24-20(25)17-8-7-16(23-12-15(22)13-28)11-18(17)14-5-3-2-4-6-14/h2-8,11,15,19,23,28H,9-10,12-13,22H2,1H3,(H,24,25)(H,26,27)/t15-,19+/m1/s1
comment: This is the parent molecule of the ester prodrug FTI-277, which is the trifluoroacetate salt (PubChem CID 395753). The ester is designed to overcome the potential for thiol-based toxicity. FTI-276 is a peptidomimetic developed as a farnesyltransferase inhibitor (FTI) <Reference id=22094/>.
iupac name: (2S)-2-[[4-[[(2R)-2-amino-3-sulfanylpropyl]amino]-2-phenylbenzoyl]amino]-4-methylsulfanylbutanoic acid
xref: CHEMBL54044
synonym: FTI-276
synonym: FTI276
approved: f
ligand name: FTI 276
type: SyntheticOrganicLigand

SC-435
in ch i key: PHAUFFBQHZENJE-VSJLXWSYSA-N
in ch i: InChI=1S/C36H55N2O6S/c1-5-7-15-36(16-8-6-2)27-45(40,41)33-26-32(43-4)31(42-3)25-30(33)34(35(36)39)28-11-13-29(14-12-28)44-24-10-9-20-38-21-17-37(18-22-38)19-23-38/h11-14,25-26,34-35,39H,5-10,15-24,27H2,1-4H3/q+1/t34-,35-/m1/s1
iupac name: (4R,5R)-5-[4-[4-(1-aza-4-azoniabicyclo[2.2.2]octan-4-yl)butoxy]phenyl]-3,3-dibutyl-7,8-dimethoxy-1,1-dioxo-4,5-dihydro-2H-1λ6-benzothiepin-4-ol
approved: f
ligand name: SC-435
type: SyntheticOrganicLigand

264W94
in ch i key: CKFWDLFFXXVSBJ-DHIUTWEWSA-N
in ch i: InChI=1S/C23H31NO4S/c1-5-7-13-23(6-2)16-29(25,26)21-15-20(28-4)19(27-3)14-18(21)22(24-23)17-11-9-8-10-12-17/h8-12,14-15,22,24H,5-7,13,16H2,1-4H3/t22-,23-/m1/s1
iupac name: (3R,5R)-3-butyl-3-ethyl-7,8-dimethoxy-5-phenyl-4,5-dihydro-2H-benzo[f][1,4]thiazepine 1,1-dioxide
xref: CHEMBL332370
approved: f
ligand name: 264W94
type: SyntheticOrganicLigand

UK-356618
in ch i key: JJHRUUKMPWUYIB-HVOSOHGQSA-N
in ch i: InChI=1S/C34H43N3O4/c1-23-21-25(19-20-29(23)27-16-10-7-11-17-27)13-12-18-28(22-30(38)37-41)32(39)36-31(34(3,4)5)33(40)35-24(2)26-14-8-6-9-15-26/h6-11,14-17,19-21,24,28,31,41H,12-13,18,22H2,1-5H3,(H,35,40)(H,36,39)(H,37,38)/t24-,28-,31-/m1/s1
comment: Selective inhibitor of MMP3 (against 13 and 9)
iupac name: (2R)-N-[(2S)-3,3-dimethyl-1-oxo-1-[[(1R)-1-phenylethyl]amino]butan-2-yl]-N'-hydroxy-2-[3-(3-methyl-4-phenylphenyl)propyl]butanediamide
xref: CHEMBL117225
synonym: UK-356,618
approved: f
ligand name: UK-356618
type: SyntheticOrganicLigand

Ac-DEVD-CHO
in ch i key: UMBVAPCONCILTL-MRHIQRDNSA-N
in ch i: InChI=1S/C20H30N4O11/c1-9(2)17(20(35)22-11(8-25)6-15(29)30)24-18(33)12(4-5-14(27)28)23-19(34)13(7-16(31)32)21-10(3)26/h8-9,11-13,17H,4-7H2,1-3H3,(H,21,26)(H,22,35)(H,23,34)(H,24,33)(H,27,28)(H,29,30)(H,31,32)/t11-,12-,13-,17-/m0/s1
comment: Caspase-3 inhibitor
iupac name: (4S)-4-[[(2S)-2-acetamido-4-hydroxy-4-oxobutanoyl]amino]-5-[[(2S)-1-[[(2S)-4-hydroxy-1,4-dioxobutan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]amino]-5-oxopentanoic acid
xref: CHEMBL417149
approved: f
ligand name: Ac-DEVD-CHO
type: SyntheticOrganicLigand

compound 1 [PMID: 17935984]
in ch i key: XRSYNYGEEYTXJV-UHFFFAOYSA-N
in ch i: InChI=1S/C20H19FN2O6/c1-2-27-12-11-20(17(24)22-19(26)23-18(20)25)29-16-9-7-15(8-10-16)28-14-5-3-13(21)4-6-14/h3-10H,2,11-12H2,1H3,(H2,22,23,24,25,26)
comment: MMP13 inhibitor
iupac name: 5-(2-ethoxyethyl)-5-[4-(4-fluorophenoxy)phenoxy]-1,3-diazinane-2,4,6-trione
xref: CHEMBL222002
approved: f
ligand name: compound 1 [PMID: 17935984]
type: SyntheticOrganicLigand

Nωpropyl-L-arginine
canonical SMILES: CCCNC(=N)NCCCC(C(=O)O)N
isomeric SMILES: CCCNC(=N)NCCC[C@@H](C(=O)O)N
in ch i key: AOMXURITGZJPKB-ZETCQYMHSA-N
in ch i: InChI=1S/C9H20N4O2/c1-2-5-12-9(11)13-6-3-4-7(10)8(14)15/h7H,2-6,10H2,1H3,(H,14,15)(H3,11,12,13)/t7-/m0/s1
comment: Nωpropyl-L-arginine is a selective inhibitor of neural nitric oxide synthase (nNOS). It is a synthetic Nω-substituted-L-arginine analogue.
iupac name: (2S)-2-amino-5-[(N'-propylcarbamimidoyl)amino]pentanoic acid
xref: CHEMBL107528
approved: f
ligand name: Nωpropyl-L-arginine
type: SyntheticOrganicLigand

GLP-1-(9-36)
in ch i key: WPNGPBPCQMDAAD-WRFZDFFOSA-N
approved: f
ligand name: GLP-1-(9-36)
type: PeptideLigand

isatin sulfonamide 34 [PMID: 11384246]
in ch i key: PKOUAUWPBMZQCH-FQEVSTJZSA-N
in ch i: InChI=1S/C26H24N2O5S/c29-25-23-16-22(13-14-24(23)27(26(25)30)17-19-8-3-1-4-9-19)34(31,32)28-15-7-10-20(28)18-33-21-11-5-2-6-12-21/h1-6,8-9,11-14,16,20H,7,10,15,17-18H2/t20-/m0/s1
comment: Caspase 7 inhibitor.
iupac name: 5-[(2S)-2-(phenoxymethyl)pyrrolidin-1-yl]sulfonyl-1-(phenylmethyl)indole-2,3-dione
xref: CHEMBL439753
approved: f
ligand name: isatin sulfonamide 34 [PMID: 11384246]
type: SyntheticOrganicLigand

(R)-EF-1520
in ch i key: CUESOMOCKVRNIW-QGZVFWFLSA-N
in ch i: InChI=1S/C22H26N2O2S2/c1-14-9-12-27-20(14)16(21-15(2)10-13-28-21)6-5-11-24(3)17-7-4-8-18-19(17)22(25)23-26-18/h6,9-10,12-13,17H,4-5,7-8,11H2,1-3H3,(H,23,25)/t17-/m1/s1
iupac name: (4R)-4-{[4,4-bis(3-methylthiophen-2-yl)but-3-en-1-yl](methyl)amino}-4,5,6,7-tetrahydro-1,2-benzoxazol-3-ol
xref: CHEMBL1628533
approved: f
ligand name: (R)-EF-1520
type: SyntheticOrganicLigand

D-aspartic acid
canonical SMILES: OC(=O)CC(C(=O)O)N
isomeric SMILES: OC(=O)C[C@H](C(=O)O)N
in ch i key: CKLJMWTZIZZHCS-UWTATZPHSA-N
in ch i: InChI=1S/C4H7NO4/c5-2(4(8)9)1-3(6)7/h2H,1,5H2,(H,6,7)(H,8,9)/t2-/m1/s1
comment: This ligand entry also represents D-aspartate (CHEBI:29994), the carboxylate anion and salt form of the acid. It is in the aspartate form that the ligand is transported across cell membranes.
iupac name: (2R)-2-aminobutanedioic acid
xref: CHEMBL29757
synonym: D-aspartate
approved: f
ligand name: D-aspartic acid
type: SyntheticOrganicLigand

azithromycin
in ch i key: MQTOSJVFKKJCRP-BICOPXKESA-N
in ch i: InChI=1S/C38H72N2O12/c1-15-27-38(10,46)31(42)24(6)40(13)19-20(2)17-36(8,45)33(52-35-29(41)26(39(11)12)16-21(3)48-35)22(4)30(23(5)34(44)50-27)51-28-18-37(9,47-14)32(43)25(7)49-28/h20-33,35,41-43,45-46H,15-19H2,1-14H3/t20-,21-,22+,23-,24-,25+,26+,27-,28+,29-,30+,31-,32+,33-,35+,36-,37-,38-/m1/s1
comment: Azithromycin is a macrolide antibacterial with broad-spectrum activity against Gram-positive and atypical bacteria. The compound also has antimalarial activity. Azithromycin is one of the watch group antibacterials in the the World Health Organization's Model List of Essential Medicines (link provided in the Classification table below). The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
iupac name: (2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)-11-[(2S,3R,4S,6R)-4-dimethylamino-3-hydroxy-6-methyloxan-2-yl]oxy-2-ethyl-3,4,10-trihydroxy-13-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-3,5,6,8,10,12,14-heptamethyl-1-oxa-6-azacyclopentadecan-15-one
xref: CHEMBL529
synonym: Zithromax
synonym: Sumamed
synonym: Azenil
synonym: Azibiot
synonym: Azifine
synonym: Azitromax
synonym: Aziwok
synonym: Aztrin
synonym: Hemomycin
synonym: Misultina
synonym: Mixoterin
synonym: Setron
synonym: Tobil
synonym: Tromix
synonym: Vinzam
synonym: Zeto
synonym: Zifin
synonym: Zithrax
synonym: Zitrim
synonym: Zitrocin
synonym: Zitromax
synonym: Zitrotek
synonym: Zmax
approved: t
ligand name: azithromycin
type: SyntheticOrganicLigand

compound 8 [PMID: 15482908]
canonical SMILES: N#Cc1cc(F)cc(c1)n1nnc(n1)c1ccccn1
isomeric SMILES: N#Cc1cc(F)cc(c1)n1nnc(n1)c1ccccn1
in ch i key: NNUSSUPIQZLYJW-UHFFFAOYSA-N
in ch i: InChI=1S/C13H7FN6/c14-10-5-9(8-15)6-11(7-10)20-18-13(17-19-20)12-3-1-2-4-16-12/h1-7H
iupac name: 3-fluoro-5-(5-pyridin-2-yltetrazol-2-yl)benzonitrile
xref: CHEMBL187107
approved: f
ligand name: compound 8 [PMID: 15482908]
type: SyntheticOrganicLigand

BMS-561392
in ch i key: QVNZBDLTUKCPGJ-SHQCIBLASA-N
in ch i: InChI=1S/C27H32N4O4/c1-17(2)14-24(25(32)30-34)31-13-12-27(28,26(31)33)20-8-10-21(11-9-20)35-16-19-15-18(3)29-23-7-5-4-6-22(19)23/h4-11,15,17,24,34H,12-14,16,28H2,1-3H3,(H,30,32)/t24-,27-/m1/s1
comment: TNF alpha converting enzyme inhibitor
iupac name: (2R)-2-[(3R)-3-amino-3-[4-[(2-methylquinolin-4-yl)methoxy]phenyl]-2-oxopyrrolidin-1-yl]-N-hydroxy-4-methylpentanamide
xref: CHEMBL489100
synonym: BMS561392
synonym: BMS 561392
synonym: DPC-333
approved: f
ligand name: BMS-561392
type: SyntheticOrganicLigand

emricasan
in ch i key: SCVHJVCATBPIHN-SJCJKPOMSA-N
in ch i: InChI=1S/C26H27F4N3O7/c1-12(31-24(38)25(39)32-16-8-6-5-7-13(16)26(2,3)4)23(37)33-17(10-19(35)36)18(34)11-40-22-20(29)14(27)9-15(28)21(22)30/h5-9,12,17H,10-11H2,1-4H3,(H,31,38)(H,32,39)(H,33,37)(H,35,36)/t12-,17-/m0/s1
comment: Emricasan is a pan caspase inhibitor. Its development as a treatment for nonalcoholic steatohepatitis (NASH) was unsuccessful.
iupac name: (3S)-3-[[(2S)-2-[[2-[(2-tert-butylphenyl)amino]-2-oxoacetyl]amino]propanoyl]amino]-4-oxo-5-(2,3,5,6-tetrafluorophenoxy)pentanoic acid
xref: CHEMBL197672
synonym: IDN-6556
synonym: PF-03491390
approved: f
ligand name: emricasan
type: SyntheticOrganicLigand

KC-12615
in ch i key: RSRHEOWMSRYTNB-PKTZIBPZSA-N
in ch i: InChI=1S/C29H34N2O6/c32-25(33)19-31-24-11-5-4-10-21(24)14-15-23(26(31)34)30-28(37)29(16-6-7-17-29)18-22(27(35)36)13-12-20-8-2-1-3-9-20/h1-5,8-11,22-23H,6-7,12-19H2,(H,30,37)(H,32,33)(H,35,36)/t22-,23+/m1/s1
comment: Drug produced by metabolic conversion of daglutril prodrug
iupac name: (2R)-2-[[1-[[(3S)-1-(carboxymethyl)-2-oxo-4,5-dihydro-3H-1-benzazepin-3-yl]carbamoyl]cyclopentyl]methyl]-4-phenylbutanoic acid
approved: f
ligand name: KC-12615
type: SyntheticOrganicLigand

daglutril
in ch i key: XMQODGUTLZXUGZ-RPBOFIJWSA-N
in ch i: InChI=1S/C31H38N2O6/c1-2-39-29(37)24(15-14-22-10-4-3-5-11-22)20-31(18-8-9-19-31)30(38)32-25-17-16-23-12-6-7-13-26(23)33(28(25)36)21-27(34)35/h3-7,10-13,24-25H,2,8-9,14-21H2,1H3,(H,32,38)(H,34,35)/t24-,25+/m1/s1
comment: This compound is a prodrug for a dual endothelin converting enzyme/neutral endopeptidase inhibitor.
iupac name: 2-[(3S)-3-[[1-[(2R)-2-ethoxycarbonyl-4-phenylbutyl]cyclopentanecarbonyl]amino]-2-oxo-4,5-dihydro-3H-1-benzazepin-1-yl]acetic acid
synonym: SLV-306
synonym: SLV 306
synonym: SLV306
approved: f
ligand name: daglutril
type: SyntheticOrganicLigand

prinomastat
in ch i key: YKPYIPVDTNNYCN-INIZCTEOSA-N
in ch i: InChI=1S/C18H21N3O5S2/c1-18(2)16(17(22)20-23)21(11-12-27-18)28(24,25)15-5-3-13(4-6-15)26-14-7-9-19-10-8-14/h3-10,16,23H,11-12H2,1-2H3,(H,20,22)/t16-/m0/s1
comment: Inhibitor of MMPs 2, 3, 9, 13, and 14 but most potent against 13
iupac name: (3S)-N-hydroxy-2,2-dimethyl-4-(4-pyridin-4-yloxyphenyl)sulfonylthiomorpholine-3-carboxamide
xref: CHEMBL75094
synonym: AG-3340
approved: f
ligand name: prinomastat
type: SyntheticOrganicLigand

[3H]pregnenolone sulphate
in ch i key: DIJBBUIOWGGQOP-QGVNFLHTSA-N
in ch i: InChI=1S/C21H32O5S/c1-13(22)17-6-7-18-16-5-4-14-12-15(26-27(23,24)25)8-10-20(14,2)19(16)9-11-21(17,18)3/h4,15-19H,5-12H2,1-3H3,(H,23,24,25)/t15-,16-,17+,18-,19-,20-,21+/m0/s1
comment: The position of the radiolabelled hydrogen atom in this compound is unspecified.
iupac name: [(3S,8S,9S,10R,13S,14S,17S)-17-acetyl-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] hydrogen sulfate
xref: CHEMBL1179605
synonym: [3H]-pregnenolone sulfate
approved: f
ligand name: [3H]pregnenolone sulphate
type: SyntheticOrganicLigand

NK3201
in ch i key: QOANBAXBOLUAFA-UHFFFAOYSA-N
in ch i: InChI=1S/C31H29N5O6/c37-21-34-25-19-33-30(23-12-5-2-6-13-23)36(31(25)41)20-27(39)35-24(18-22-10-3-1-4-11-22)29(40)26(38)14-9-17-42-28-15-7-8-16-32-28/h1-8,10-13,15-16,19,21,24H,9,14,17-18,20H2,(H,34,37)(H,35,39)
comment: Chymase inhibitor
iupac name: N-(3,4-dioxo-1-phenyl-7-pyridin-2-yloxyheptan-2-yl)-2-(5-formamido-6-oxo-2-phenylpyrimidin-1-yl)acetamide
synonym: NK-3201
synonym: NK 3201
approved: f
ligand name: NK3201
type: SyntheticOrganicLigand

fasidotrilat
canonical SMILES: SCC(C(=O)NC(C(=O)O)C)Cc1ccc2c(c1)OCO2
in ch i key: TXSINLUUGRGAJO-WCBMZHEXSA-N
in ch i: InChI=1S/C14H17NO5S/c1-8(14(17)18)15-13(16)10(6-21)4-9-2-3-11-12(5-9)20-7-19-11/h2-3,5,8,10,21H,4,6-7H2,1H3,(H,15,16)(H,17,18)/t8-,10+/m0/s1
comment: Active drug formed from the metabolism of prodrug fasidotril. Fasidotrilat has not been assigned an INN itself.
iupac name: (2S)-2-[[(2S)-2-(1,3-benzodioxol-5-ylmethyl)-3-sulfanylpropanoyl]amino]propanoic acid
xref: CHEMBL325055
approved: f
ligand name: fasidotrilat
type: SyntheticOrganicLigand

fasidotril
in ch i key: KKBIUAUSZKGNOA-HNAYVOBHSA-N
in ch i: InChI=1S/C23H25NO6S/c1-15(23(27)28-12-17-6-4-3-5-7-17)24-22(26)19(13-31-16(2)25)10-18-8-9-20-21(11-18)30-14-29-20/h3-9,11,15,19H,10,12-14H2,1-2H3,(H,24,26)/t15-,19+/m0/s1
comment: Prodrug of fasidotrilat, a combined ACE and NEP inhibitor. There is some ambiguity online as to the exact stereochemistry of fasidotril. Our structure is drawn from the INN document and matches that represented in the PubChem and ChEMBL entries linked to above.
iupac name: phenylmethyl (2S)-2-[[(2S)-2-(acetylsulfanylmethyl)-3-(1,3-benzodioxol-5-yl)propanoyl]amino]propanoate
xref: CHEMBL325695
synonym: aladotril
synonym: BP-1137
approved: f
ligand name: fasidotril
type: SyntheticOrganicLigand

1-methylcyclopropanecarboxylic acid
canonical SMILES: OC(=O)C1(C)CC1
isomeric SMILES: OC(=O)C1(C)CC1
in ch i key: DIZKLZKLNKQFGB-UHFFFAOYSA-N
in ch i: InChI=1S/C5H8O2/c1-5(2-3-5)4(6)7/h2-3H2,1H3,(H,6,7)
iupac name: 1-methylcyclopropane-1-carboxylic acid
approved: f
ligand name: 1-methylcyclopropanecarboxylic acid
type: SyntheticOrganicLigand

trans-2-methylcrotonic acid
canonical SMILES: CC(=CC)C(=O)O
isomeric SMILES: C/C(=C/C)/C(=O)O
in ch i key: UIERETOOQGIECD-ONEGZZNKSA-N
in ch i: InChI=1S/C5H8O2/c1-3-4(2)5(6)7/h3H,1-2H3,(H,6,7)/b4-3+
iupac name: 2-methylbut-2-enoic acid
xref: CHEMBL52416
synonym: tiglic acid
approved: f
ligand name: trans-2-methylcrotonic acid
type: SyntheticOrganicLigand

CTEP
canonical SMILES: Clc1nccc(c1)C#Cc1nc(n(c1C)c1ccc(cc1)OC(F)(F)F)C
isomeric SMILES: Clc1nccc(c1)C#Cc1nc(n(c1C)c1ccc(cc1)OC(F)(F)F)C
in ch i key: GOHCTCOGYKAJLZ-UHFFFAOYSA-N
comment: CTEP is a negative allosteric modulator (NAM) of the glutamate metabotropic receptor 5 (mGlu5) GPCR <Reference id=31633/><Reference id=21789/>. Structurally, CTEP and <Ligand id=9309/> and are analogues. CTEP has a notably longer half-life in rodents (49 hours) than basimglurant (~10 hours), so is better suited for rodents studies requiring chronic exposure/treatment.
iupac name: 2-chloro-4-[2-[2,5-dimethyl-1-[4-(trifluoromethoxy)phenyl]imidazol-4-yl]ethynyl]pyridine
synonym: compound 3 [PMID: 25565255]
approved: f
ligand name: CTEP
type: SyntheticOrganicLigand

WX-UK1
in ch i key: ISJSHQTWOHGCMM-NDEPHWFRSA-N
in ch i: InChI=1S/C32H47N5O5S/c1-8-42-32(39)37-14-12-36(13-15-37)31(38)28(17-23-10-9-11-24(16-23)30(33)34)35-43(40,41)29-26(21(4)5)18-25(20(2)3)19-27(29)22(6)7/h9-11,16,18-22,28,35H,8,12-15,17H2,1-7H3,(H3,33,34)/t28-/m0/s1
comment: Drug from the prodrug <Ligand id=6497/>. This compound has urokinase-type plasminogen activator inhbitory effect, but also inhibits other trypsin-like enzymes <Reference id=22311/>.
iupac name: ethyl 4-[(2S)-3-(3-carbamimidoylphenyl)-2-[[2,4,6-tri(propan-2-yl)phenyl]sulfonylamino]propanoyl]piperazine-1-carboxylate
xref: CHEMBL107955
synonym: compound 2r-L
synonym: UKI-1
approved: f
ligand name: WX-UK1
type: SyntheticOrganicLigand

upamostat
in ch i key: CYCFEEXTLQGJEL-XEOXDSMQSA-N
in ch i: InChI=1S/C32H47N5O6S/c1-8-43-32(39)37-14-12-36(13-15-37)31(38)29(17-24-10-9-11-25(16-24)20-33-35-40)34-44(41,42)30-27(22(4)5)18-26(21(2)3)19-28(30)23(6)7/h9-11,16,18-23,29,34-35,40H,8,12-15,17H2,1-7H3/b33-20+/t29-/m0/s1
comment: Upamostat (WX-671) is an oral serine protease inhibitor prodrug. Its principal molecular target is plasminogen activator, urokinase (uPA; PLAU) <Reference id=43672/>. The uPA system plays an important role in tumour invasion and metastasis. The active substance is WX-UK1.
iupac name: ethyl 4-[(2S)-3-{3-[(1E)-[(hydroxyamino)imino]methyl]phenyl}-2-[2,4,6-tris(propan-2-yl)benzenesulfonamido]propanoyl]piperazine-1-carboxylate
synonym: WX-671
synonym: Mesupron
approved: f
ligand name: upamostat
type: SyntheticOrganicLigand

MRS 2219
canonical SMILES: Cc1ncc2c(c1O)COP(=O)(OC2)O
isomeric SMILES: Cc1ncc2c(c1O)COP(=O)(OC2)O
in ch i key: KCAJHODRYGNBSX-UHFFFAOYSA-N
in ch i: InChI=1S/C8H10NO5P/c1-5-8(10)7-4-14-15(11,12)13-3-6(7)2-9-5/h2,10H,3-4H2,1H3,(H,11,12)
iupac name: 4-hydroxy-10-methyl-4-oxo-3,5-dioxa-9-aza-4$l^{5}-phosphabicyclo[5.4.0]undeca-1(11),7,9-trien-11-ol
xref: CHEMBL74121
synonym: MRS-2220
synonym: MRS2219
approved: f
ligand name: MRS 2219
type: SyntheticOrganicLigand

trametinib
in ch i key: LIRYPHYGHXZJBZ-UHFFFAOYSA-N
in ch i: InChI=1S/C26H23FIN5O4/c1-13-22-21(23(31(3)24(13)35)30-20-10-7-15(28)11-19(20)27)25(36)33(17-8-9-17)26(37)32(22)18-6-4-5-16(12-18)29-14(2)34/h4-7,10-12,17,30H,8-9H2,1-3H3,(H,29,34)
comment: Trametinib is a Type-3 kinase inhibitor. Marketed formulations contain trametinib dimethyl sulfoxide (PubChem CID 50992434).
iupac name: N-[3-[3-cyclopropyl-5-[(2-fluoro-4-iodophenyl)amino]-6,8-dimethyl-2,4,7-trioxopyrido[3,4-e]pyrimidin-1-yl]phenyl]acetamide
xref: CHEMBL2103875
synonym: GSK212
synonym: GSK1120212
synonym: GSK1120212B
synonym: JTP 74057
synonym: Mekinist®
synonym: trametinib dimethyl sulfoxide
approved: t
ligand name: trametinib
type: SyntheticOrganicLigand

dabrafenib
in ch i key: BFSMGDJOXZAERB-UHFFFAOYSA-N
comment: Dabrafenib is a Type-1.5 kinase inhibitor.
iupac name: N-[3-[5-(2-aminopyrimidin-4-yl)-2-tert-butyl-1,3-thiazol-4-yl]-2-fluorophenyl]-2,6-difluorobenzenesulfonamide
xref: CHEMBL2028663
synonym: GSK2118436A
synonym: GSK2118436
synonym: Tafinlar®
approved: t
ligand name: dabrafenib
type: SyntheticOrganicLigand

S-OOPP
canonical SMILES: O=C(NC1COC1=O)CCc1ccccc1
isomeric SMILES: O=C(N[C@H]1COC1=O)CCc1ccccc1
in ch i key: UUEMOTWYJKOUPP-JTQLQIEISA-N
in ch i: InChI=1S/C12H13NO3/c14-11(13-10-8-16-12(10)15)7-6-9-4-2-1-3-5-9/h1-5,10H,6-8H2,(H,13,14)/t10-/m0/s1
iupac name: N-[(3S)-2-oxooxetan-3-yl]-3-phenylpropanamide
xref: CHEMBL1214256
approved: f
ligand name: S-OOPP
type: SyntheticOrganicLigand

candoxatril
in ch i key: ZTWZVMIYIIVABD-OEMFJLHTSA-N
in ch i: InChI=1S/C29H41NO7/c1-35-15-16-36-19-23(27(33)37-25-12-9-20-5-4-6-22(20)17-25)18-29(13-2-3-14-29)28(34)30-24-10-7-21(8-11-24)26(31)32/h9,12,17,21,23-24H,2-8,10-11,13-16,18-19H2,1H3,(H,30,34)(H,31,32)/t21-,23-,24+/m0/s1
comment: This is the prodrug of candoxitrilat. This ligand is represented in PubChem by the entry CID 5362417.
iupac name: cis-4-{[(1-{(2S)-3-(2,3-dihydro-1H-inden-5-yloxy)-2-[(2-methoxyethoxy)methyl]-3-oxopropyl}cyclopentyl)carbonyl]amino}cyclohexanecarboxylic acid
synonym: Candoxatrilat
approved: f
ligand name: candoxatril
type: SyntheticOrganicLigand

candoxatrilat
in ch i key: ACZWIDANLCXHBM-HRCADAONSA-N
in ch i: InChI=1S/C20H33NO7/c1-27-10-11-28-13-15(18(24)25)12-20(8-2-3-9-20)19(26)21-16-6-4-14(5-7-16)17(22)23/h14-16H,2-13H2,1H3,(H,21,26)(H,22,23)(H,24,25)/t14-,15-,16+/m0/s1
comment: Drug produced by metabolism of candoxatril prodrug. This ligand is represented in PubChem by the entry CID 443380.
iupac name: cis-4-[({1-[(2S)-2-carboxy-3-(2-methoxyethoxy)propyl]cyclopentyl}carbonyl)amino]cyclohexanecarboxylic acid
xref: CHEMBL434492
synonym: UK-69578
approved: f
ligand name: candoxatrilat
type: SyntheticOrganicLigand

TUG-891
in ch i key: LPGBXHWIQNZEJB-UHFFFAOYSA-N
in ch i: InChI=1S/C23H21FO3/c1-16-2-7-18(8-3-16)22-12-9-20(24)14-19(22)15-27-21-10-4-17(5-11-21)6-13-23(25)26/h2-5,7-12,14H,6,13,15H2,1H3,(H,25,26)
iupac name: 3-(4-{[5-fluoro-2-(4-methylphenyl)phenyl]methoxy}phenyl)propanoic acid
xref: CHEMBL2058533
synonym: TUG 891
synonym: TUG891
approved: f
ligand name: TUG-891
type: SyntheticOrganicLigand

avagacestat
in ch i key: XEAOPVUAMONVLA-QGZVFWFLSA-N
comment: Avagacestat is an oral gamma-secretase inhibitor designed for the selective inhibition of A-beta generation relative to Notch substrates in the treatment of Alzheimer's Disease but Phase 2 data did not support advancement to Phase 3
iupac name: (2R)-5,5,5-trifluoro-2-(N-{[2-fluoro-4-(1,2,4-oxadiazol-3-yl)phenyl]methyl}4-chlorobenzenesulfonamido)pentanamide
xref: CHEMBL1090771
synonym: BMS-708163
approved: f
ligand name: avagacestat
type: SyntheticOrganicLigand

compound 1 [PMID: 23589301]
in ch i key: LCRQPJWEPVZEBE-UHFFFAOYSA-N
comment: Please note that this compound appears in the publication and on PubChem with IUPAC name 3-benzyl-4-(cyclopropyl-(4-(2,5-dichlorophenyl)thiazol-2-yl)amino)-4-oxobutanoic acid, which differs to the IUPAC name listed above.
iupac name: 3-{cyclopropyl[4-(2,5-dichlorophenyl)-1,3-thiazol-2-yl]carbamoyl}-4-phenylbutanoic acid
approved: f
ligand name: compound 1 [PMID: 23589301]
type: SyntheticOrganicLigand

CATPB
in ch i key: QOSIJVVNNGXEKE-INIZCTEOSA-N
iupac name: (3S)-3-[2-(3-chlorophenyl)acetamido]-4-[4-(trifluoromethyl)phenyl]butanoic acid
approved: f
ligand name: CATPB
type: SyntheticOrganicLigand

XMT-1191
in ch i key: HRLDHINFRLTOEQ-UZHVHHFFSA-N
in ch i: InChI=1S/C29H40N2O8/c1-18(2)8-13-22-28(3,39-22)26-25(36-4)21(14-15-29(26)17-37-29)38-27(35)30-16-19-9-11-20(12-10-19)31-23(32)6-5-7-24(33)34/h8-12,21-22,25-26H,5-7,13-17H2,1-4H3,(H,30,35)(H,31,32)(H,33,34)/t21-,22-,25-,26-,28+,29+/m1/s1
comment: XMT-1191 is released from XMT-1107 congugate prodrug to a PMF polymer (hence no PubChem structure for XMT-1107)
iupac name: (3S)-N-hydroxy-4-{4-[(4-hydroxybut-2-yn-1-yl)oxy]benzenesulfonyl}-2,2-dimethylthiomorpholine-3-carboxamide
approved: f
ligand name: XMT-1191
type: SyntheticOrganicLigand

AMG-837
in ch i key: ZOPNBMMVVZRSGH-NRFANRHFSA-N
in ch i: InChI=1S/C26H21F3O3/c1-2-4-21(16-25(30)31)20-9-13-24(14-10-20)32-17-18-5-3-6-22(15-18)19-7-11-23(12-8-19)26(27,28)29/h3,5-15,21H,16-17H2,1H3,(H,30,31)/t21-/m0/s1
iupac name: (3S)-3-[4-({3-[4-(trifluoromethyl)phenyl]phenyl}methoxy)phenyl]hex-4-ynoic acid
xref: CHEMBL1829173
synonym: AMG837
synonym: AMG 837
approved: f
ligand name: AMG-837
type: SyntheticOrganicLigand

camostat
in ch i key: XASIMHXSUQUHLV-UHFFFAOYSA-N
in ch i: InChI=1S/C20H22N4O5/c1-24(2)17(25)12-28-18(26)11-13-3-9-16(10-4-13)29-19(27)14-5-7-15(8-6-14)23-20(21)22/h3-10H,11-12H2,1-2H3,(H4,21,22,23)
comment: Publications and data are also linked to the camostat mesilate salt (PubChem CID 5284360). There is an active metabolite reported as FOY 251 but this also maps to the mesylate salt (PubChem CID 130394), with the parent compound being PubChem CID 130395 SARS-CoV-2 and COVID-19: Inhibition of TMPRSS2 partially blocks entry of SARS-CoV-2 into Caco-2 cells <Reference id=38932/>, a result which indicates an opportunity for repurposing this already approved drug for COVID-19. Complete blockade of SARS-CoV-2 entry can be achieved by combined inhibition of TMPRSS2 (by camostat) and the endosomal cysteine proteases cathepsins B and L (by <Ligand id=10714/>; E-64d). In August 2020 Edinburgh University, the CRUK's Centre for Drug Development and Latus Therapeutics began the Phase 2/3 SPIKE-1 trial (NCT04455815) of camostat in non-hospitalised CoV-2 positive patients, to determine if the drug can reduce the progression of COVID-19 symptoms- access CRUK's trial webpage here.
iupac name: [4-[2-(2-dimethylamino-2-oxoethoxy)-2-oxoethyl]phenyl] 4-(diaminomethylideneamino)benzoate
xref: CHEMBL590799
synonym: ONO-3403
approved: t
ligand name: camostat
type: SyntheticOrganicLigand

fasiglifam
in ch i key: BZCALJIHZVNMGJ-HSZRJFAPSA-N
in ch i: InChI=1S/C29H32O7S/c1-19-12-25(34-10-5-11-37(3,32)33)13-20(2)29(19)22-7-4-6-21(14-22)17-35-24-8-9-26-23(15-28(30)31)18-36-27(26)16-24/h4,6-9,12-14,16,23H,5,10-11,15,17-18H2,1-3H3,(H,30,31)/t23-/m1/s1
comment: Fasiglifam is a positive allosteric modulator/partial agonist of the free fatty acid receptor 1 (FFA1, a.k.a. GPR40) <Reference id=30935/>. In the presence of endogenous free fatty acids (FFAs) fasiglifam enhances insulin secretion, by binding to an allosteric site distinct from the orthosteric FFA binding site. On its own, it elicits a low level of insulin secretion. These findings indicate that fasiglifam acts cooperatively with FFAs to promote insulin secretion.
iupac name: 2-[(3S)-6-({3-[4-(3-methanesulfonylpropoxy)-2,6-dimethylphenyl]phenyl}methoxy)-2,3-dihydro-1-benzofuran-3-yl]acetic acid
xref: CHEMBL1829174
synonym: TAK875
synonym: TAK 875
synonym: TAK-875
approved: f
ligand name: fasiglifam
type: SyntheticOrganicLigand

TUG-770
canonical SMILES: N#CCc1ccccc1C#Cc1ccc(c(c1)F)CCC(=O)O
isomeric SMILES: N#CCc1ccccc1C#Cc1ccc(c(c1)F)CCC(=O)O
in ch i key: KIZUBVPJNPVIIN-UHFFFAOYSA-N
in ch i: InChI=1S/C19H14FNO2/c20-18-13-14(6-8-17(18)9-10-19(22)23)5-7-15-3-1-2-4-16(15)11-12-21/h1-4,6,8,13H,9-11H2,(H,22,23)
iupac name: 3-(4-{2-[2-(cyanomethyl)phenyl]ethynyl}-2-fluorophenyl)propanoic acid
xref: CHEMBL2386353
synonym: TUG770
approved: f
ligand name: TUG-770
type: SyntheticOrganicLigand

apratastat
in ch i key: MAVDNGWEBZTACC-HNNXBMFYSA-N
in ch i: InChI=1S/C17H22N2O6S2/c1-17(2)15(16(21)18-22)19(9-12-26-17)27(23,24)14-7-5-13(6-8-14)25-11-4-3-10-20/h5-8,15,20,22H,9-12H2,1-2H3,(H,18,21)/t15-/m0/s1
comment: Apratastat (TMI-005) is an orally active dual TACE (ADAM17)/MMP13 inhibitor that was developed for the potential treatment of inflammation <Reference id=22328/>. TACE = TNF α-converting enzyme, which is a well validated therapeutic target for the treatment of rheumatoid arthritis. Inhibition of MMP13 (a peptidase that preferentially degrades type II collagen and aggrecan) is relevant since this is predicted to prevent the degradation of cartilage in rheumatoid arthritis <Reference id=34555/><Reference id=34556/>.
iupac name: (3S)-N-hydroxy-4-[4-(4-hydroxybut-2-ynoxy)phenyl]sulfonyl-2,2-dimethylthiomorpholine-3-carboxamide
xref: CHEMBL206815
synonym: compound 5h [PMID: 16426848]
synonym: TMI005
synonym: TMI-05
approved: f
ligand name: apratastat
type: SyntheticOrganicLigand

ORM-10103
in ch i key: GZONLGPIHCCJOI-UHFFFAOYSA-N
in ch i: InChI=1S/C20H16N2O4/c23-22(24)16-7-11-20(21-13-16)25-17-8-10-19-15(12-17)6-9-18(26-19)14-4-2-1-3-5-14/h1-5,7-8,10-13,18H,6,9H2
iupac name: 5-nitro-2-(2-phenylchroman-6-yl)oxypyridine
approved: f
ligand name: ORM-10103
type: SyntheticOrganicLigand

G36
in ch i key: QTOCPACSSHFGOY-ZCCHDVMBSA-N
in ch i: InChI=1S/C22H22BrNO2/c1-12(2)13-6-7-19-16(8-13)14-4-3-5-15(14)22(24-19)17-9-20-21(10-18(17)23)26-11-25-20/h3-4,6-10,12,14-15,22,24H,5,11H2,1-2H3/t14-,15+,22-/m1/s1
iupac name: (3aS,4R,9bR)-4-(6-bromo-2H-1,3-benzodioxol-5-yl)-8-(propan-2-yl)-3H,3aH,4H,5H,9bH-cyclopenta[c]quinoline
synonym: G-36
approved: f
ligand name: G36
type: SyntheticOrganicLigand

compound 13 [PMID: 15686941]
canonical SMILES: Cc1cnc(c(n1)C(=O)Nc1ccccn1)N
isomeric SMILES: Cc1cnc(c(n1)C(=O)Nc1ccccn1)N
in ch i key: NAQODRYELYCKDS-UHFFFAOYSA-N
in ch i: InChI=1S/C11H11N5O/c1-7-6-14-10(12)9(15-7)11(17)16-8-4-2-3-5-13-8/h2-6H,1H3,(H2,12,14)(H,13,16,17)
iupac name: 3-amino-6-methyl-N-pyridin-2-ylpyrazine-2-carboxamide
xref: CHEMBL183081
approved: f
ligand name: compound 13 [PMID: 15686941]
type: SyntheticOrganicLigand

odanacatib
in ch i key: FWIVDMJALNEADT-SFTDATJTSA-N
comment: Odanacatib, a cathepsin K inhibitor, has clinically shown prevention of bone loss in osteoporosis. However, in Sept 2016 Merck ceased development because of an increased risk of stroke in the Phase 3 results (see the In the Pipeline commentary)
xref: CHEMBL481611
synonym: MK-0822
approved: f
ligand name: odanacatib
type: SyntheticOrganicLigand

alvelestat
in ch i key: QNQZWEGMKJBHEM-UHFFFAOYSA-N
comment: AZD9668 is a potent, selective and reversible inhibitor of human neutrophil elastase. It was developed as having the potential to be effective for neutrophil-driven inflammatory lung diseases, such as bronchiectasis and COPD <Reference id=22359/>. Since the phase II studies did not show clear efficacy for COPD this compound is now listed in the AstraZeneca Open Innovation Clinical Compound Bank for repurposing proposals. There is ambiguity on PubChem in the assigned nomenclature and stuctures for this compound, as CID 71587812 has been incorrectly assigned alvelestat as a synonym.
iupac name: N-[(5-methanesulfonylpyridin-2-yl)methyl]-6-methyl-5-(1-methyl-1H-pyrazol-5-yl)-2-oxo-1-[3-(trifluoromethyl)phenyl]-1,2-dihydropyridine-3-carboxamide
synonym: KB-105160
synonym: AZD-9668
synonym: AZD9668
synonym: AZD 9668
approved: f
ligand name: alvelestat
type: SyntheticOrganicLigand

LY2886721
in ch i key: NIDRNVHMMDAAIK-YPMLDQLKSA-N
comment: BACE1 inhibitor for Alzheimer's disease
iupac name: N-{3-[(4aS,7aS)-2-amino-4H,4aH,5H,7H,7aH-furo[3,4-d][1,3]thiazin-7a-yl]-4-fluorophenyl}-5-fluoropyridine-2-carboxamide
xref: CHEMBL2396989
synonym: LY 2886721
synonym: LY-2886721
approved: f
ligand name: LY2886721
type: SyntheticOrganicLigand

cis-10 [PMID: 15771457]
in ch i key: IOCYQQQCJYMWDT-KDYLLFBJSA-N
in ch i: InChI=1S/C20H25NO3/c1-4-13-11-16-12-15(7-10-18(16)21-20(13)24-3)19(22)14-5-8-17(23-2)9-6-14/h7,10-12,14,17H,4-6,8-9H2,1-3H3/t14-,17+
comment: This ligand is represented in PubChem without chiral centres by CID 10245890.
iupac name: 3-ethyl-2-methoxy-6-{[(1s,4s)-4-methoxycyclohexyl]carbonyl}quinoline
approved: f
ligand name: cis-10 [PMID: 15771457]
type: SyntheticOrganicLigand

morphanthridine
canonical SMILES: c1ccc2c(c1)Cc1ccccc1C=N2
isomeric SMILES: c1ccc2c(c1)Cc1ccccc1C=N2
in ch i key: IDWNSAXOQLJYOF-UHFFFAOYSA-N
in ch i: InChI=1S/C14H11N/c1-2-7-13-10-15-14-8-4-3-6-12(14)9-11(13)5-1/h1-8,10H,9H2
iupac name: 11H-benzo[c][1]benzazepine
xref: CHEMBL1085101
approved: f
ligand name: morphanthridine
type: SyntheticOrganicLigand

dibenzoxazepine
canonical SMILES: c1ccc2c(c1)Oc1ccccc1C=N2
isomeric SMILES: c1ccc2c(c1)Oc1ccccc1C=N2
in ch i key: NPUACKRELIJTFM-UHFFFAOYSA-N
in ch i: InChI=1S/C13H9NO/c1-3-7-12-10(5-1)9-14-11-6-2-4-8-13(11)15-12/h1-9H
iupac name: benzo[b][1,5]benzoxazepine
xref: CHEMBL1085100
synonym: CR gas
approved: f
ligand name: dibenzoxazepine
type: SyntheticOrganicLigand

NCFP
in ch i key: WBXKMHFMMCOTOK-UHFFFAOYSA-N
iupac name: N-[4-chloro-2-[(4-fluoro-1,3-dioxoisoindol-2-yl)methyl]phenyl]pyridine-2-carboxamide
approved: f
ligand name: NCFP
type: SyntheticOrganicLigand

bivalirudin
in ch i key: OIRCOABEOLEUMC-GEJPAHFPSA-N
comment: Bivalirudin is a peptide congener of hirudin, the naturally occurring anticoagulant found in the saliva of the medicinal leech Hirudo medicinalis.
iupac name: (4S)-4-[(2S)-2-[(2S)-2-[(2S)-2-{2-[(2S)-2-(2-{2-[2-(2-{[(2S)-1-[(2S)-2-{[(2S)-1-[(2R)-2-amino-3-phenylpropanoyl]pyrrolidin-2-yl]formamido}-5-carbamimidamidopentanoyl]pyrrolidin-2-yl]formamido}acetamido)acetamido]acetamido}acetamido)-3-carbamoylpropanamido]acetamido}-3-carboxypropanamido]-3-phenylpropanamido]-4-carboxybutanamido]-4-{[(2S,3S)-1-[(2S)-2-{[(1S)-3-carboxy-1-{[(1S)-3-carboxy-1-{[(1S)-1-{[(1S)-1-carboxy-3-methylbutyl]carbamoyl}-2-(4-hydroxyphenyl)ethyl]carbamoyl}propyl]carbamoyl}propyl]carbamoyl}pyrrolidin-1-yl]-3-methyl-1-oxopentan-2-yl]carbamoyl}butanoic acid
xref: CHEMBL2103749
synonym: Angiomax®
synonym: Hirulog-1
approved: t
ligand name: bivalirudin
type: PeptideLigand

fosinoprilat
in ch i key: WOIWWYDXDVSWAZ-RTWAWAEBSA-N
in ch i: InChI=1S/C23H34NO5P/c25-22(17-30(28,29)14-8-7-11-18-9-3-1-4-10-18)24-16-20(15-21(24)23(26)27)19-12-5-2-6-13-19/h1,3-4,9-10,19-21H,2,5-8,11-17H2,(H,26,27)(H,28,29)/t20-,21+/m1/s1
comment: Fosinoprilat is the active drug produced by metabolism of the prodrug fosinopril.
iupac name: (2S,4S)-4-cyclohexyl-1-[2-(hydroxy-(4-phenylbutyl)phosphoryl)acetyl]pyrrolidine-2-carboxylic acid
xref: CHEMBL581
synonym: SQ-27519
approved: t
ligand name: fosinoprilat
type: SyntheticOrganicLigand

1'-acetoxychavicol acetate
canonical SMILES: C=CC(c1ccc(cc1)OC(=O)C)OC(=O)C
isomeric SMILES: C=C[C@@H](c1ccc(cc1)OC(=O)C)OC(=O)C
in ch i key: JAMQIUWGGBSIKZ-ZDUSSCGKSA-N
in ch i: InChI=1S/C13H14O4/c1-4-13(17-10(3)15)11-5-7-12(8-6-11)16-9(2)14/h4-8,13H,1H2,2-3H3/t13-/m0/s1
iupac name: [4-[(1S)-1-acetyloxyprop-2-enyl]phenyl] acetate
xref: CHEMBL323727
approved: f
ligand name: 1'-acetoxychavicol acetate
type: SyntheticOrganicLigand

lepirudin
in ch i key: FIBJDTSHOUXTKV-BRHMIFOHSA-N
comment: Discontinued (not withdrawn). The drug is a recombinant form of hirudin, the salivary anticoagulant found in leeches (see UniProt P01050), but has two amino acid modifications; substitution of Leu1 for Ile and no sulfate group on Tyr63. The PubChem entry linked to above represents the chemical structure of Lepirudin.
synonym: 1-L-leucine-2-L-threonine-63-desulfohirudin
synonym: Refludan®
approved: t
ligand name: lepirudin
type: PeptideLigand

tanomastat
in ch i key: JXAGDPXECXQWBC-LJQANCHMSA-N
in ch i: InChI=1S/C23H19ClO3S/c24-20-12-10-17(11-13-20)16-6-8-18(9-7-16)22(25)14-19(23(26)27)15-28-21-4-2-1-3-5-21/h1-13,19H,14-15H2,(H,26,27)/t19-/m1/s1
comment: This compound failed testing in Phase 3 clinical trials.
iupac name: (2S)-4-[4-(4-chlorophenyl)phenyl]-4-oxo-2-(phenylsulfanylmethyl)butanoic acid
xref: CHEMBL261932
synonym: BAY-12-9566
synonym: BAY-129566
synonym: BAY 12-9566
approved: f
ligand name: tanomastat
type: SyntheticOrganicLigand

pralnacasan
in ch i key: CXAGHAZMQSCAKJ-WAHHBDPQSA-N
in ch i: InChI=1S/C26H29N5O7/c1-2-37-26-18(14-21(33)38-26)29-23(34)19-8-5-13-30-20(32)10-9-17(25(36)31(19)30)28-24(35)22-16-7-4-3-6-15(16)11-12-27-22/h3-4,6-7,11-12,17-19,26H,2,5,8-10,13-14H2,1H3,(H,28,35)(H,29,34)/t17-,18-,19-,26+/m0/s1
comment: Pralnacasan (VX-740) is a selective, non-peptide caspase 1 inhibitor that was developed by Vertex for anti-inflammatory potential. Inhibition of caspase 1 is a small molecule strategy developed as an alternative to the use of anti-IL-1β neutralising antibodies, such as <Ligand id=6773/>, or the dimeric fusion protein <Ligand id=6790/> that acts as a IL-1 trap. Pralnacasan is a prodrug whose active metabolite is VRT-018858 <Reference id=38292/>.
iupac name: (1S,9S)-N-[(2R,3S)-2-ethoxy-5-oxooxolan-3-yl]-9-(isoquinoline-1-carbonylamino)-6,10-dioxo-2,3,4,7,8,9-hexahydro-1H-pyridazino[1,2-a]diazepine-1-carboxamide
xref: CHEMBL437526
synonym: VX740
synonym: VX-740
approved: f
ligand name: pralnacasan
type: SyntheticOrganicLigand

cipemastat
in ch i key: GFUITADOEPNRML-SJORKVTESA-N
in ch i: InChI=1S/C22H36N4O5/c1-22(2)20(29)26(21(30)24(22)3)14-17(18(27)23-31)16(13-15-9-5-6-10-15)19(28)25-11-7-4-8-12-25/h15-17,31H,4-14H2,1-3H3,(H,23,27)/t16-,17+/m1/s1
comment: Cipemastat is a selective matrix metalloproteinase-1 inhibitor.
iupac name: (2R,3R)-3-(cyclopentylmethyl)-N-hydroxy-4-oxo-4-piperidin-1-yl-2-[(3,4,4-trimethyl-2,5-dioxoimidazolidin-1-yl)methyl]butanamide
xref: CHEMBL115653
synonym: Ro 28-2653
synonym: Trocade
approved: f
ligand name: cipemastat
type: SyntheticOrganicLigand

compound 42 [PMID: 17189691]
canonical SMILES: O=C(C1CC=Cc2c1[nH]c(=O)o2)Nc1cccc(n1)C
isomeric SMILES: O=C(C1CC=Cc2c1[nH]c(=O)o2)Nc1cccc(n1)C
in ch i key: ILTICRNSZLAODU-UHFFFAOYSA-N
in ch i: InChI=1S/C14H13N3O3/c1-8-4-2-7-11(15-8)16-13(18)9-5-3-6-10-12(9)17-14(19)20-10/h2-4,6-7,9H,5H2,1H3,(H,17,19)(H,15,16,18)
iupac name: N-(6-methylpyridin-2-yl)-2-oxo-2,3,4,5-tetrahydro-1,3-benzoxazole-4-carboxamide
approved: f
ligand name: compound 42 [PMID: 17189691]
type: SyntheticOrganicLigand

GSK2193874
in ch i key: UIVOZBSCHXCGPS-UHFFFAOYSA-N
iupac name: 7-bromo-N-(1-phenylcyclopropyl)-3-[(4-piperidin-1-ylpiperidin-1-yl) methyl]-2-[3-(trifluoromethyl)phenyl]quinoline-4-carboxamide
synonym: GSK 2193874
synonym: GSK-2193874
approved: f
ligand name: GSK2193874
type: SyntheticOrganicLigand

zofenoprilat
canonical SMILES: SCC(C(=O)N1CC(CC1C(=O)O)Sc1ccccc1)C
in ch i key: UQWLOWFDKAFKAP-WXHSDQCUSA-N
in ch i: InChI=1S/C15H19NO3S2/c1-10(9-20)14(17)16-8-12(7-13(16)15(18)19)21-11-5-3-2-4-6-11/h2-6,10,12-13,20H,7-9H2,1H3,(H,18,19)/t10-,12+,13+/m1/s1
comment: Drug from metabolism of zofenopril prodrug. Note the PDB ligand structure is for a different target, not ACE
iupac name: (2S,4S)-1-[(2S)-2-methyl-3-sulfanylpropanoyl]-4-phenylsulfanylpyrrolidine-2-carboxylic acid
xref: CHEMBL16332
approved: t
ligand name: zofenoprilat
type: SyntheticOrganicLigand

zofenopril
in ch i key: IAIDUHCBNLFXEF-MNEFBYGVSA-N
in ch i: InChI=1S/C22H23NO4S2/c1-15(14-28-22(27)16-8-4-2-5-9-16)20(24)23-13-18(12-19(23)21(25)26)29-17-10-6-3-7-11-17/h2-11,15,18-19H,12-14H2,1H3,(H,25,26)/t15-,18+,19+/m1/s1
comment: Metabolised to the active from zofenoprilat. The United States Adopted Name (USAN) for this compound is zofenopril calcium (PubChem CID 3033690).
iupac name: (2S,4S)-1-[(2S)-3-(benzoylsulfanyl)-2-methylpropanoyl]-4-phenylsulfanylpyrrolidine-2-carboxylic acid
xref: CHEMBL331378
synonym: SQ-26900
synonym: SO-26991
approved: t
ligand name: zofenopril
type: SyntheticOrganicLigand

cilazaprilat
in ch i key: UVAUYSRYXACKSC-ULQDDVLXSA-N
in ch i: InChI=1S/C20H27N3O5/c24-18-15(8-4-12-22-13-5-9-17(20(27)28)23(18)22)21-16(19(25)26)11-10-14-6-2-1-3-7-14/h1-3,6-7,15-17,21H,4-5,8-13H2,(H,25,26)(H,27,28)/t15-,16-,17-/m0/s1
comment: Active compound derived by metabolism of prodrug cilazapril. Technically this compound is not an approved drug, as the approved drug is administered as a prodrug which is then metabolised to this active form. We mark both the prodrug and active form as 'approved' for clarity. Note that the prodrug, cilazapril, does not appear to have marketing approval for human use in the US or EU, although individual countries may have approved use of this drug.
iupac name: (1S,9S)-9-[[(2S)-1-hydroxy-1-oxo-4-phenylbutan-2-yl]amino]-10-oxo-1,2,3,4,6,7,8,9-octahydropyridazino[1,2-a]diazepine-1-carboxylic acid
xref: CHEMBL2104578
synonym: Ro 31-3113
approved: t
ligand name: cilazaprilat
type: SyntheticOrganicLigand

cilazapril
in ch i key: HHHKFGXWKKUNCY-FHWLQOOXSA-N
in ch i: InChI=1S/C22H31N3O5/c1-2-30-22(29)18(13-12-16-8-4-3-5-9-16)23-17-10-6-14-24-15-7-11-19(21(27)28)25(24)20(17)26/h3-5,8-9,17-19,23H,2,6-7,10-15H2,1H3,(H,27,28)/t17-,18-,19-/m0/s1
comment: Cilazapril is a prodrug. It is metabolically converted to the drug cilazaprilat. Cilazapril does not appear to have marketing approval for human use in the US or EU, although national approval agencies may have granted marketing authorisation.
iupac name: (1S,9S)-9-[[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino]-10-oxo-1,2,3,4,6,7,8,9-octahydropyridazino[1,2-a]diazepine-1-carboxylic acid
xref: CHEMBL515606
synonym: Ro 31-2848006
synonym: Inhibace®
synonym: Vascace®
approved: t
ligand name: cilazapril
type: SyntheticOrganicLigand

desirudin
in ch i key: XYWBJDRHGNULKG-OUMQNGNKSA-N
comment: Desirudin is an anticoagulant. The drug is a recombinant form of hirudin (P01050), the salivary anticoagulant found in leeches.
xref: CHEMBL1201662
synonym: CGP39393
synonym: CGP 39393
synonym: Iprivask
synonym: CGP-39393
approved: t
ligand name: desirudin
type: PeptideLigand

2-iodoacetamide
canonical SMILES: NC(=O)CI
isomeric SMILES: NC(=O)CI
in ch i key: PGLTVOMIXTUURA-UHFFFAOYSA-N
in ch i: InChI=1S/C2H4INO/c3-1-2(4)5/h1H2,(H2,4,5)
iupac name: 2-Iodoacetamide
xref: CHEMBL276727
synonym: iodoacetamide
approved: f
ligand name: 2-iodoacetamide
type: SyntheticOrganicLigand

fosinopril
in ch i key: BIDNLKIUORFRQP-XYGFDPSESA-N
in ch i: InChI=1S/C30H46NO7P/c1-4-28(33)37-30(22(2)3)38-39(36,18-12-11-15-23-13-7-5-8-14-23)21-27(32)31-20-25(19-26(31)29(34)35)24-16-9-6-10-17-24/h5,7-8,13-14,22,24-26,30H,4,6,9-12,15-21H2,1-3H3,(H,34,35)/t25-,26+,30+,39-/m1/s1
comment: Fosinopril is a prodrug which is metabolised to the active drug fosinoprilat. Fosinopril belongs to the angiotensin-converting enzyme (ACE) inhibitor drug family. There is some ambiguity in the literature and on other resources as to the exact stereochemistry of fosinopril. The structure shown here matches that specified by the INN document.
iupac name: (2S,4S)-4-cyclohexyl-1-[2-[[(1S)-2-methyl-1-propanoyloxypropoxy]-(4-phenylbutyl)phosphoryl]acetyl]pyrrolidine-2-carboxylic acid
xref: CHEMBL3039598
synonym: SQ-28555
synonym: Acecor
synonym: Staril
synonym: Monopril®
approved: t
ligand name: fosinopril
type: SyntheticOrganicLigand

trandolaprilat
in ch i key: AHYHTSYNOHNUSH-HXFGRODQSA-N
in ch i: InChI=1S/C22H30N2O5/c1-14(23-17(21(26)27)12-11-15-7-3-2-4-8-15)20(25)24-18-10-6-5-9-16(18)13-19(24)22(28)29/h2-4,7-8,14,16-19,23H,5-6,9-13H2,1H3,(H,26,27)(H,28,29)/t14-,16+,17-,18-,19-/m0/s1
comment: Generated by metabolic conversion of the prodrug trandolapril
iupac name: (2S,3aR,7aS)-1-[(2S)-2-[[(2S)-1-hydroxy-1-oxo-4-phenylbutan-2-yl]amino]propanoyl]-2,3,3a,4,5,6,7,7a-octahydroindole-2-carboxylic acid
xref: CHEMBL1201387
approved: t
ligand name: trandolaprilat
type: SyntheticOrganicLigand

trandolapril
in ch i key: VXFJYXUZANRPDJ-WTNASJBWSA-N
in ch i: InChI=1S/C24H34N2O5/c1-3-31-24(30)19(14-13-17-9-5-4-6-10-17)25-16(2)22(27)26-20-12-8-7-11-18(20)15-21(26)23(28)29/h4-6,9-10,16,18-21,25H,3,7-8,11-15H2,1-2H3,(H,28,29)/t16-,18+,19-,20-,21-/m0/s1
comment: Metabolized to its biologically active diacid (drug) trandolaprilat in the liver.
iupac name: (2S,3aR,7aS)-1-[(2S)-2-[[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino]propanoyl]-2,3,3a,4,5,6,7,7a-octahydroindole-2-carboxylic acid
xref: CHEMBL1519
synonym: Mavik®
synonym: RU-44570
synonym: CI-907
synonym: indolapril
synonym: Tarka
synonym: Gopten
approved: t
ligand name: trandolapril
type: SyntheticOrganicLigand

dipraglurant
canonical SMILES: Fc1ccc2n(c1)cc(n2)CCC#Cc1ccccn1
isomeric SMILES: Fc1ccc2n(c1)cc(n2)CCC#Cc1ccccn1
in ch i key: LZXMUJCJAWVHPZ-UHFFFAOYSA-N
in ch i: InChI=1S/C16H12FN3/c17-13-8-9-16-19-15(12-20(16)11-13)7-2-1-5-14-6-3-4-10-18-14/h3-4,6,8-12H,2,7H2
iupac name: 2-(4-{6-fluoroimidazo[1,2-a]pyridin-2-yl}but-1-yn-1-yl)pyridine
xref: CHEMBL2346738
synonym: ADX48621
approved: f
ligand name: dipraglurant
type: SyntheticOrganicLigand

compound 53 [PMID: 23434029]
canonical SMILES: Clc1nccc(n1)NC(=O)c1nc(n(c1C)c1ccccc1)C
isomeric SMILES: Clc1nccc(n1)NC(=O)c1nc(n(c1C)c1ccccc1)C
in ch i key: YCJZWBZJSYLMPB-UHFFFAOYSA-N
in ch i: InChI=1S/C16H14ClN5O/c1-10-14(15(23)20-13-8-9-18-16(17)21-13)19-11(2)22(10)12-6-4-3-5-7-12/h3-9H,1-2H3,(H,18,20,21,23)
iupac name: N-(2-chloropyrimidin-4-yl)-2,5-dimethyl-1-phenyl-1H-imidazole-4-carboxamide
approved: f
ligand name: compound 53 [PMID: 23434029]
type: SyntheticOrganicLigand

compound 23 [PMID: 17590335]
canonical SMILES: N#Cc1cc(F)cc(c1)c1ccc2c(c1)nc(cc2)C
isomeric SMILES: N#Cc1cc(F)cc(c1)c1ccc2c(c1)nc(cc2)C
in ch i key: SDOLISUYGVMVBK-UHFFFAOYSA-N
in ch i: InChI=1S/C17H11FN2/c1-11-2-3-13-4-5-14(9-17(13)20-11)15-6-12(10-19)7-16(18)8-15/h2-9H,1H3
iupac name: 3-fluoro-5-(2-methylquinolin-7-yl)benzonitrile
xref: CHEMBL232188
approved: f
ligand name: compound 23 [PMID: 17590335]
type: SyntheticOrganicLigand

compound 18 [PMID: 17723296]
canonical SMILES: COc1cc(C#N)cc(c1)c1ncc2c(n1)nc(cc2)C
isomeric SMILES: COc1cc(C#N)cc(c1)c1ncc2c(n1)nc(cc2)C
in ch i key: NGRPBCOEAPBKCI-UHFFFAOYSA-N
in ch i: InChI=1S/C16H12N4O/c1-10-3-4-12-9-18-15(20-16(12)19-10)13-5-11(8-17)6-14(7-13)21-2/h3-7,9H,1-2H3
iupac name: 3-methoxy-5-(7-methylpyrido[2,3-d]pyrimidin-2-yl)benzonitrile
xref: CHEMBL393843
approved: f
ligand name: compound 18 [PMID: 17723296]
type: SyntheticOrganicLigand

compound 18 [PMID: 21927650]
canonical SMILES: N#Cc1cc(F)cc(c1)c1ccc2c(c1)NC(S2)C
isomeric SMILES: N#Cc1cc(F)cc(c1)c1ccc2c(c1)NC(S2)C
in ch i key: DUFLWBPOXGXKEK-UHFFFAOYSA-N
in ch i: InChI=1S/C15H11FN2S/c1-9-18-14-7-11(2-3-15(14)19-9)12-4-10(8-17)5-13(16)6-12/h2-7,9,18H,1H3
iupac name: 3-fluoro-5-(2-methyl-2,3-dihydro-1,3-benzothiazol-5-yl)benzonitrile
approved: f
ligand name: compound 18 [PMID: 21927650]
type: SyntheticOrganicLigand

sivelestat
in ch i key: BTGNGJJLZOIYID-UHFFFAOYSA-N
in ch i: InChI=1S/C20H22N2O7S/c1-20(2,3)19(26)29-13-8-10-14(11-9-13)30(27,28)22-16-7-5-4-6-15(16)18(25)21-12-17(23)24/h4-11,22H,12H2,1-3H3,(H,21,25)(H,23,24)
comment: Some data is linked to salt forms eg sodium tetra hydrate (PubChem CID 23663985).
iupac name: 2-[[2-[[4-(2,2-dimethylpropanoyloxy)phenyl]sulfonylamino]benzoyl]amino]acetic acid
xref: CHEMBL76688
synonym: Ono-EI-600
synonym: LY544349
synonym: ONO-5046
synonym: Elaspol®
approved: t
ligand name: sivelestat
type: SyntheticOrganicLigand

AZD6538
canonical SMILES: N#Cc1ccc(nc1)c1noc(n1)c1cc(F)cc(c1)C#N
isomeric SMILES: N#Cc1ccc(nc1)c1noc(n1)c1cc(F)cc(c1)C#N
in ch i key: PBVKGEMPZBKZOA-UHFFFAOYSA-N
in ch i: InChI=1S/C15H6FN5O/c16-12-4-10(7-18)3-11(5-12)15-20-14(21-22-15)13-2-1-9(6-17)8-19-13/h1-5,8H
iupac name: 6-[5-(3-cyano-5-fluorophenyl)-1,2,4-oxadiazol-3-yl]pyridine-3-carbonitrile
xref: CHEMBL2164552
synonym: AZD-6538
synonym: AZD 6538
approved: f
ligand name: AZD6538
type: SyntheticOrganicLigand

AZD9272
canonical SMILES: N#Cc1cc(F)cc(c1)c1onc(n1)c1ccc(cn1)F
isomeric SMILES: N#Cc1cc(F)cc(c1)c1onc(n1)c1ccc(cn1)F
in ch i key: RBSPCALDSNXWEP-UHFFFAOYSA-N
in ch i: InChI=1S/C14H6F2N4O/c15-10-1-2-12(18-7-10)13-19-14(21-20-13)9-3-8(6-17)4-11(16)5-9/h1-5,7H
iupac name: 3-fluoro-5-[3-(5-fluoropyridin-2-yl)-1,2,4-oxadiazol-5-yl]benzonitrile
xref: CHEMBL2164551
synonym: AZD 9272
synonym: AZD-9272
approved: f
ligand name: AZD9272
type: SyntheticOrganicLigand

VU0366058
canonical SMILES: N#Cc1cnc(nc1c1ccc(cc1)F)Nc1nc2c(o1)cccc2
isomeric SMILES: N#Cc1cnc(nc1c1ccc(cc1)F)Nc1nc2c(o1)cccc2
in ch i key: OBFRNKSPNQSVFR-UHFFFAOYSA-N
in ch i: InChI=1S/C18H10FN5O/c19-13-7-5-11(6-8-13)16-12(9-20)10-21-17(23-16)24-18-22-14-3-1-2-4-15(14)25-18/h1-8,10H,(H,21,22,23,24)
iupac name: 2-[(1,3-benzoxazol-2-yl)amino]-4-(4-fluorophenyl)pyrimidine-5-carbonitrile
approved: f
ligand name: VU0366058
type: SyntheticOrganicLigand

compound 27 [PMID: 20598884]
canonical SMILES: N#Cc1cc(F)cc(c1)C(=O)Nc1cccc(c1)Cl
isomeric SMILES: N#Cc1cc(F)cc(c1)C(=O)Nc1cccc(c1)Cl
in ch i key: FNDUFJARTKDXEF-UHFFFAOYSA-N
in ch i: InChI=1S/C14H8ClFN2O/c15-11-2-1-3-13(7-11)18-14(19)10-4-9(8-17)5-12(16)6-10/h1-7H,(H,18,19)
iupac name: N-(3-chlorophenyl)-3-cyano-5-fluorobenzamide
xref: CHEMBL1209202
approved: f
ligand name: compound 27 [PMID: 20598884]
type: SyntheticOrganicLigand

compound 8 [PMID: 20598884]
canonical SMILES: N#Cc1cc(F)cc(c1)C(=O)Nc1scc(n1)C
isomeric SMILES: N#Cc1cc(F)cc(c1)C(=O)Nc1scc(n1)C
in ch i key: KTQZJPKEGPXLRL-UHFFFAOYSA-N
in ch i: InChI=1S/C12H8FN3OS/c1-7-6-18-12(15-7)16-11(17)9-2-8(5-14)3-10(13)4-9/h2-4,6H,1H3,(H,15,16,17)
iupac name: 3-cyano-5-fluoro-N-(4-methyl-1,3-thiazol-2-yl)benzamide
xref: CHEMBL1209201
approved: f
ligand name: compound 8 [PMID: 20598884]
type: SyntheticOrganicLigand

GSK2210875
canonical SMILES: O=C(OC(c1sc2n(c1C)ncn2)C)Nc1ccccc1
isomeric SMILES: O=C(O[C@@H](c1sc2n(c1C)ncn2)C)Nc1ccccc1
in ch i key: AOUUMBPBMVOBSP-SNVBAGLBSA-N
in ch i: InChI=1S/C14H14N4O2S/c1-9-12(21-13-15-8-16-18(9)13)10(2)20-14(19)17-11-6-4-3-5-7-11/h3-8,10H,1-2H3,(H,17,19)/t10-/m1/s1
iupac name: [(1R)-1-(6-methyl-[1,3]thiazolo[2,3-e][1,2,4]triazol-5-yl)ethyl] N-phenylcarbamate
xref: CHEMBL1630057
synonym: GSK-2210875
approved: f
ligand name: GSK2210875
type: SyntheticOrganicLigand

SP203
canonical SMILES: FCc1scc(n1)C#Cc1cc(F)cc(c1)C#N
isomeric SMILES: FCc1scc(n1)C#Cc1cc(F)cc(c1)C#N
in ch i key: WTLBLIGPXACYET-UHFFFAOYSA-N
in ch i: InChI=1S/C13H6F2N2S/c14-6-13-17-12(8-18-13)2-1-9-3-10(7-16)5-11(15)4-9/h3-5,8H,6H2
iupac name: 3-fluoro-5-[2-[2-(fluoromethyl)-1,3-thiazol-4-yl]ethynyl]benzonitrile
xref: CHEMBL229429
synonym: SP-203
synonym: SP 203
approved: f
ligand name: SP203
type: SyntheticOrganicLigand

5PAM523
in ch i key: JOBPCEDWVKYVKZ-OCCSQVGLSA-N
in ch i: InChI=1S/C20H18F2N4O2/c1-12-2-3-14(11-26(12)20(27)13-4-6-15(21)7-5-13)18-24-19(28-25-18)17-9-8-16(22)10-23-17/h4-10,12,14H,2-3,11H2,1H3/t12-,14+/m1/s1
iupac name: 5-fluoro-2-{3-[(3S,6R)-1-[(4-fluorophenyl)carbonyl]-6-methylpiperidin-3-yl]-1,2,4-oxadiazol-5-yl}pyridine
approved: f
ligand name: 5PAM523
type: SyntheticOrganicLigand

triazine compound PC10
in ch i key: XZNHZFUKGYYVMQ-UHFFFAOYSA-N
in ch i: InChI=1S/C28H27F2N7O4/c1-41-23-12-4-19(5-13-23)16-36-26(35-27(39)37(28(36)40)17-18-2-8-21(29)9-3-18)33-15-14-32-25(31)34-24(38)20-6-10-22(30)11-7-20/h2-13H,14-17H2,1H3,(H,33,35,39)(H3,31,32,34,38)
iupac name: 4-fluoro-N-[N'-[2-[[5-[(4-fluorophenyl)methyl]-1-[(4-methoxyphenyl)methyl]-4,6-dioxo-1,3,5-triazin-2-yl]amino]ethyl]carbamimidoyl]benzamide
approved: f
ligand name: triazine compound PC10
type: SyntheticOrganicLigand

super cinnamaldehyde
canonical SMILES: CC(=O)C=C1c2ccccc2N(C1=O)C
isomeric SMILES: CC(=O)/C=C/1/c2ccccc2N(C1=O)C
in ch i key: CZKBLHCEDVWPRN-JXMROGBWSA-N
in ch i: InChI=1S/C12H11NO2/c1-8(14)7-10-9-5-3-4-6-11(9)13(2)12(10)15/h3-7H,1-2H3/b10-7+
iupac name: (3E)-1-methyl-3-(2-oxopropylidene)indol-2-one
xref: CHEMBL402589
approved: f
ligand name: super cinnamaldehyde
type: SyntheticOrganicLigand

triazine compound PC7
in ch i key: INQAREWWDULMAD-UHFFFAOYSA-N
in ch i: InChI=1S/C21H24FN7O3/c1-32-17-8-4-15(5-9-17)12-28-19(26-11-10-25-18(23)24)27-20(30)29(21(28)31)13-14-2-6-16(22)7-3-14/h2-9H,10-13H2,1H3,(H4,23,24,25)(H,26,27,30)
iupac name: 2-[2-[[5-[(4-fluorophenyl)methyl]-1-[(4-methoxyphenyl)methyl]-4,6-dioxo-1,3,5-triazin-2-yl]amino]ethyl]guanidine
xref: CHEMBL550577
approved: f
ligand name: triazine compound PC7
type: SyntheticOrganicLigand

compound 29b [PMID: 20809633]
in ch i key: MVXAKOGJWVQPKC-UHFFFAOYSA-N
in ch i: InChI=1S/C20H16FN3O/c1-2-14-10-15(21)12-16(11-14)24-9-5-7-19-18(13-24)23-20(25-19)17-6-3-4-8-22-17/h1,3-4,6,8,10-12H,5,7,9,13H2
iupac name: 2-[5-(3-ethynyl-5-fluorophenyl)-4H,5H,6H,7H,8H-[1,3]oxazolo[4,5-c]azepin-2-yl]pyridine
approved: f
ligand name: compound 29b [PMID: 20809633]
type: SyntheticOrganicLigand

compound 16m [PMID: 19931453]
in ch i key: QABUURICQJOWID-MRXNPFEDSA-N
in ch i: InChI=1S/C19H23ClN4O/c1-3-16-6-4-5-9-24(16)19(25)14-10-17(20)18(22-11-14)23-15-8-7-13(2)21-12-15/h7-8,10-12,16H,3-6,9H2,1-2H3,(H,22,23)/t16-/m1/s1
iupac name: [5-chloro-6-[(6-methylpyridin-3-yl)amino]pyridin-3-yl]-[(2R)-2-ethylpiperidin-1-yl]methanone
xref: CHEMBL593590
approved: f
ligand name: compound 16m [PMID: 19931453]
type: SyntheticOrganicLigand

GRN-529
canonical SMILES: FC(Oc1ccc(cc1C#Cc1ccccn1)C(=O)N1Cc2c(C1)cccn2)F
isomeric SMILES: FC(Oc1ccc(cc1C#Cc1ccccn1)C(=O)N1Cc2c(C1)cccn2)F
in ch i key: JITMSIRHBAVREW-UHFFFAOYSA-N
in ch i: InChI=1S/C22H15F2N3O2/c23-22(24)29-20-9-7-16(12-15(20)6-8-18-5-1-2-10-25-18)21(28)27-13-17-4-3-11-26-19(17)14-27/h1-5,7,9-12,22H,13-14H2
iupac name: 2-{2-[2-(difluoromethoxy)-5-({5H,6H,7H-pyrrolo[3,4-b]pyridin-6-yl}carbonyl)phenyl]ethynyl}pyridine
xref: CHEMBL3122220
approved: f
ligand name: GRN-529
type: SyntheticOrganicLigand

compound 16a [PMID: 14697765]
canonical SMILES: COc1cc(ccc1c1ccccn1)c1nc2n(c1)cccc2
isomeric SMILES: COc1cc(ccc1c1ccccn1)c1nc2n(c1)cccc2
in ch i key: DNCGFJANVDVZIZ-UHFFFAOYSA-N
in ch i: InChI=1S/C19H15N3O/c1-23-18-12-14(8-9-15(18)16-6-2-4-10-20-16)17-13-22-11-5-3-7-19(22)21-17/h2-13H,1H3
iupac name: 2-(3-methoxy-4-pyridin-2-ylphenyl)imidazo[1,2-a]pyridine
approved: f
ligand name: compound 16a [PMID: 14697765]
type: SyntheticOrganicLigand

compound 11a [PMID: 14697765]
canonical SMILES: COc1cc(ccc1c1ccccn1)C1Nc2c(O1)cccc2
isomeric SMILES: COc1cc(ccc1c1ccccn1)C1Nc2c(O1)cccc2
in ch i key: DNFFCLRSKDXRKM-UHFFFAOYSA-N
in ch i: InChI=1S/C19H16N2O2/c1-22-18-12-13(9-10-14(18)15-6-4-5-11-20-15)19-21-16-7-2-3-8-17(16)23-19/h2-12,19,21H,1H3
iupac name: 2-[3-methoxy-4-(pyridin-2-yl)phenyl]-2,3-dihydro-1,3-benzoxazole
approved: f
ligand name: compound 11a [PMID: 14697765]
type: SyntheticOrganicLigand

[3H]methoxy-PEPy
canonical SMILES: COc1cncc(c1)C#Cc1ccccn1
isomeric SMILES: C([3H])(Oc1cncc(c1)C#Cc1ccccn1)([3H])[3H]
in ch i key: VRTFKUFTEWQHDD-RLXJOQACSA-N
in ch i: InChI=1S/C13H10N2O/c1-16-13-8-11(9-14-10-13)5-6-12-4-2-3-7-15-12/h2-4,7-10H,1H3/i1T3
iupac name: 3-(2-pyridin-2-ylethynyl)-5-(tritritiomethoxy)pyridine
xref: CHEMBL1169452
approved: f
ligand name: [3H]methoxy-PEPy
type: SyntheticOrganicLigand

VU0364289
canonical SMILES: N#Cc1ccccc1N1CCN(CC1)C(=O)COCc1ccccc1
isomeric SMILES: N#Cc1ccccc1N1CCN(CC1)C(=O)COCc1ccccc1
in ch i key: LTPGKAICNBCBPT-UHFFFAOYSA-N
in ch i: InChI=1S/C20H21N3O2/c21-14-18-8-4-5-9-19(18)22-10-12-23(13-11-22)20(24)16-25-15-17-6-2-1-3-7-17/h1-9H,10-13,15-16H2
iupac name: 2-{4-[2-(benzyloxy)acetyl]piperazin-1-yl}benzonitrile
xref: CHEMBL1688365
synonym: VU 0364289
approved: f
ligand name: VU0364289
type: SyntheticOrganicLigand

VU0361747
canonical SMILES: OC1CCN(CC1)C(=O)c1ccc(nc1)C#Cc1cccc(c1)F
isomeric SMILES: OC1CCN(CC1)C(=O)c1ccc(nc1)C#Cc1cccc(c1)F
in ch i key: ZKKOJUZGUBLAJQ-UHFFFAOYSA-N
in ch i: InChI=1S/C19H17FN2O2/c20-16-3-1-2-14(12-16)4-6-17-7-5-15(13-21-17)19(24)22-10-8-18(23)9-11-22/h1-3,5,7,12-13,18,23H,8-11H2
iupac name: 1-({6-[2-(3-fluorophenyl)ethynyl]pyridin-3-yl}carbonyl)piperidin-4-ol
xref: CHEMBL2431185
approved: f
ligand name: VU0361747
type: SyntheticOrganicLigand

VU0240382
canonical SMILES: O=C1NCCc2c1ccc(c2)C#Cc1ccccc1
isomeric SMILES: O=C1NCCc2c1ccc(c2)C#Cc1ccccc1
in ch i key: BOVJHNHRQNCDEQ-UHFFFAOYSA-N
in ch i: InChI=1S/C17H13NO/c19-17-16-9-8-14(12-15(16)10-11-18-17)7-6-13-4-2-1-3-5-13/h1-5,8-9,12H,10-11H2,(H,18,19)
iupac name: 6-(2-phenylethynyl)-1,2,3,4-tetrahydroisoquinolin-1-one
xref: CHEMBL1682799
approved: f
ligand name: VU0240382
type: SyntheticOrganicLigand

VU0092273
canonical SMILES: OC1CCN(CC1)C(=O)c1ccc(cc1)C#Cc1ccccc1
isomeric SMILES: OC1CCN(CC1)C(=O)c1ccc(cc1)C#Cc1ccccc1
in ch i key: FPDBSDNGFNDSSK-UHFFFAOYSA-N
in ch i: InChI=1S/C20H19NO2/c22-19-12-14-21(15-13-19)20(23)18-10-8-17(9-11-18)7-6-16-4-2-1-3-5-16/h1-5,8-11,19,22H,12-15H2
iupac name: (4-hydroxypiperidin-1-yl)-[4-(2-phenylethynyl)phenyl]methanone
xref: CHEMBL1684241
synonym: VU 0092273
approved: f
ligand name: VU0092273
type: SyntheticOrganicLigand

compound 41 [PMID: 23434029]
in ch i key: YQFYIHPLHNEXNE-UHFFFAOYSA-N
in ch i: InChI=1S/C18H17FN4O/c1-11-5-4-6-16(20-11)22-18(24)17-12(2)23(13(3)21-17)15-9-7-14(19)8-10-15/h4-10H,1-3H3,(H,20,22,24)
iupac name: 1-(4-fluorophenyl)-2,5-dimethyl-N-(6-methylpyridin-2-yl)-1H-imidazole-4-carboxamide
xref: CHEMBL2346725
approved: f
ligand name: compound 41 [PMID: 23434029]
type: SyntheticOrganicLigand

compound 24 [PMID: 23374867]
in ch i key: DMJNZMXZSQWBRT-RDTXWAMCSA-N
in ch i: InChI=1S/C24H25N5OS/c1-4-6-17-7-5-8-20(25-17)21-22(15-9-10-19-16(12-15)13-29(3)27-19)28-31-24(21)26-23(30)18-11-14(18)2/h5,7-10,12-14,18H,4,6,11H2,1-3H3,(H,26,30)/t14-,18-/m1/s1
iupac name: (1R,2R)-2-methyl-N-[3-(2-methylindazol-5-yl)-4-(6-propylpyridin-2-yl)-1,2-thiazol-5-yl]cyclopropane-1-carboxamide
xref: CHEMBL2334980
approved: f
ligand name: compound 24 [PMID: 23374867]
type: SyntheticOrganicLigand

tetrahydrocannabivarin
canonical SMILES: CCCc1cc(O)c2c(c1)OC(C1C2C=C(C)CC1)(C)C
in ch i key: ZROLHBHDLIHEMS-HUUCEWRRSA-N
in ch i: InChI=1S/C19H26O2/c1-5-6-13-10-16(20)18-14-9-12(2)7-8-15(14)19(3,4)21-17(18)11-13/h9-11,14-15,20H,5-8H2,1-4H3/t14-,15-/m1/s1
iupac name: (6aR,10aR)-6,6,9-trimethyl-3-propyl-6a,7,8,10a-tetrahydrobenzo[c]chromen-1-ol
xref: CHEMBL2387541
synonym: THCV
synonym: delta9-THCV
synonym: Δ9-THCV
synonym: Δ9-tetrahydrocannabivarin
approved: f
ligand name: tetrahydrocannabivarin
type: NaturalProductLigand

carveol
canonical SMILES: CC(=C)C1CC=C(C(C1)O)C
isomeric SMILES: CC(=C)C1CC=C(C(C1)O)C
in ch i key: BAVONGHXFVOKBV-UHFFFAOYSA-N
in ch i: InChI=1S/C10H16O/c1-7(2)9-5-4-8(3)10(11)6-9/h4,9-11H,1,5-6H2,2-3H3
iupac name: 2-methyl-5-prop-1-en-2-ylcyclohex-2-en-1-ol
xref: CHEMBL1385229
synonym: L-carveol
approved: f
ligand name: carveol
type: NaturalProductLigand

CPPZ
in ch i key: XNOMHUDLVRWWLV-UHFFFAOYSA-N
iupac name: 1-[4-(2-chloro-4-fluorophenyl)piperazin-1-yl]-2-(pyridin-4-ylmethoxy)ethanone
xref: CHEMBL1289113
approved: f
ligand name: CPPZ
type: SyntheticOrganicLigand

dihydrocarveol
canonical SMILES: CC(=C)C1CCC(C(C1)O)C
isomeric SMILES: CC(=C)C1CCC(C(C1)O)C
in ch i key: KRCZYMFUWVJCLI-UHFFFAOYSA-N
in ch i: InChI=1S/C10H18O/c1-7(2)9-5-4-8(3)10(11)6-9/h8-11H,1,4-6H2,2-3H3
iupac name: 2-methyl-5-prop-1-en-2-ylcyclohexan-1-ol
synonym: neodihydrocarveol
approved: f
ligand name: dihydrocarveol
type: SyntheticOrganicLigand

VU0424465
canonical SMILES: Fc1cccc(c1)C#Cc1ccc(nc1)C(=O)NC(C(O)(C)C)C
isomeric SMILES: Fc1cccc(c1)C#Cc1ccc(nc1)C(=O)N[C@@H](C(O)(C)C)C
in ch i key: ZPKZAFDYFVJULO-CYBMUJFWSA-N
in ch i: InChI=1S/C19H19FN2O2/c1-13(19(2,3)24)22-18(23)17-10-9-15(12-21-17)8-7-14-5-4-6-16(20)11-14/h4-6,9-13,24H,1-3H3,(H,22,23)/t13-/m1/s1
iupac name: 5-[2-(3-fluorophenyl)ethynyl]-N-[(2R)-3-hydroxy-3-methylbutan-2-yl]pyridine-2-carboxamide
xref: CHEMBL2431192
synonym: ML273
approved: f
ligand name: VU0424465
type: SyntheticOrganicLigand

VU0404251
in ch i key: VOYBJCDMLJODRK-CYBMUJFWSA-N
in ch i: InChI=1S/C19H23FN2O2/c1-13(19(2,3)4)22-18(23)15-8-9-17(21-11-15)24-12-14-6-5-7-16(20)10-14/h5-11,13H,12H2,1-4H3,(H,22,23)/t13-/m1/s1
iupac name: N-[(2R)-3,3-dimethylbutan-2-yl]-6-[(3-fluorophenyl)methoxy]pyridine-3-carboxamide
xref: CHEMBL2151817
approved: f
ligand name: VU0404251
type: SyntheticOrganicLigand

AG-26
canonical SMILES: COc1ccc(cc1)CCNC(=O)Nc1ccc(cc1)Cl
isomeric SMILES: COc1ccc(cc1)CCNC(=O)Nc1ccc(cc1)Cl
in ch i key: OVFMMJNKICPJJH-UHFFFAOYSA-N
in ch i: InChI=1S/C16H17ClN2O2/c1-21-15-8-2-12(3-9-15)10-11-18-16(20)19-14-6-4-13(17)5-7-14/h2-9H,10-11H2,1H3,(H2,18,19,20)
iupac name: 3-(4-chlorophenyl)-1-[2-(4-methoxyphenyl)ethyl]urea
xref: CHEMBL1289260
synonym: AG26
synonym: AG 26
approved: f
ligand name: AG-26
type: SyntheticOrganicLigand

[3H]CTEP
canonical SMILES: Clc1nccc(c1)C#Cc1nc(n(c1C)c1ccc(cc1)OC(F)(F)F)C
isomeric SMILES: Clc1nccc(c1)C#Cc1nc(n(c1C)c1ccc(cc1)OC(F)(F)F)C
in ch i key: GOHCTCOGYKAJLZ-UHFFFAOYSA-N
comment: The position of the tritiated hydrogen atom in this radiolabelled ligand is unspecified by the reference.
iupac name: 2-chloro-4-[2-[2,5-dimethyl-1-[4-(trifluoromethoxy)phenyl]imidazol-4-yl]ethynyl]pyridine
approved: f
ligand name: [3H]CTEP
type: SyntheticOrganicLigand

compound 30 [PMID: 21757343]
in ch i key: GCSDBTCZHROCLZ-GOSISDBHSA-N
in ch i: InChI=1S/C20H18ClN3OS/c1-13-10-17(14-4-2-5-15(21)11-14)23-12-16(13)18-6-3-8-24(18)20(25)19-22-7-9-26-19/h2,4-5,7,9-12,18H,3,6,8H2,1H3/t18-/m1/s1
iupac name: 2-(3-chlorophenyl)-4-methyl-5-[(2R)-1-[(1,3-thiazol-2-yl)carbonyl]pyrrolidin-2-yl]pyridine
xref: CHEMBL1808901
approved: f
ligand name: compound 30 [PMID: 21757343]
type: SyntheticOrganicLigand

compound 47 [PMID: 21295468]
canonical SMILES: CN1CCOc2c1ncc(c2)COc1ccccc1
isomeric SMILES: CN1CCOc2c1ncc(c2)COc1ccccc1
in ch i key: XAGOQHLVLYAAMO-UHFFFAOYSA-N
in ch i: InChI=1S/C15H16N2O2/c1-17-7-8-18-14-9-12(10-16-15(14)17)11-19-13-5-3-2-4-6-13/h2-6,9-10H,7-8,11H2,1H3
iupac name: 4-methyl-7-(phenoxymethyl)-2H,3H,4H-pyrido[3,2-b][1,4]oxazine
xref: CHEMBL1681799
approved: f
ligand name: compound 47 [PMID: 21295468]
type: SyntheticOrganicLigand

SF-21
canonical SMILES: Clc1ccc(cc1)S(=O)(=O)NC1CCCCC1N1CCOCC1
isomeric SMILES: Clc1ccc(cc1)S(=O)(=O)NC1CCCCC1N1CCOCC1
in ch i key: AYQCZQKMGKDZPS-UHFFFAOYSA-N
iupac name: 4-chloro-N-(2-morpholin-4-ylcyclohexyl)benzenesulfonamide
xref: CHEMBL1521361
approved: f
ligand name: SF-21
type: SyntheticOrganicLigand

SF-11
in ch i key: WFFKVDICECGSHN-UHFFFAOYSA-N
iupac name: 3-(4-chlorophenyl)-5-methyl-4-[2-(4-methylphenyl)sulfonylpyrazol-3-yl]-1,2-oxazole
xref: CHEMBL548708
approved: f
ligand name: SF-11
type: SyntheticOrganicLigand