compound 39 [PMID: 34982553]   Click here for help

GtoPdb Ligand ID: 11852

Synonyms: H2N-c[X-R-L-S-X]-K-G-P-(D-1Nal)
Compound class: Synthetic organic
Comment: Compound 39 is a macrocyclic analogue of the apelin receptor agonist [Pyr1]apelin-13, that was designed to have a reduced molecular weight [1]. 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.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 24
Hydrogen bond donors 14
Rotatable bonds 26
Topological polar surface area 395.48
Molecular weight 1019.56
XLogP -0.32
No. Lipinski's rules broken 3
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Canonical SMILES NCCCC[C@@H](C(=O)NCC(=O)N1CCC[C@H]1C(=O)N[C@@H](C(=O)O)Cc1cccc2c1cccc2)NC(=O)[C@@H]1C/C=C\C[C@H](N)C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N1)CO)CC(C)C)CCCNC(=N)N
Isomeric SMILES N[C@@H]1C(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CO)C(=O)N[C@@H](C/C=C\C1)C(=O)N[C@@H](CCCCN)C(=O)NCC(=O)N1CCC[C@H]1C(=O)N[C@@H](C(=O)O)Cc1c2ccccc2ccc1
InChI 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
Classification Click here for help
Compound class Synthetic organic
Synonyms Click here for help
Database Links Click here for help
Specialist databases
GPCRdb Ligand compound 39 [PMID: 34982553]
Other databases
GtoPdb PubChem SID 461663408
PubChem CID 162679539
Search Google for chemical match using the InChIKey VXVNSDXGZQXERO-NXDMJTDOSA-N
Search Google for chemicals with the same backbone VXVNSDXGZQXERO
UniChem Compound Search for chemical match using the InChIKey VXVNSDXGZQXERO-NXDMJTDOSA-N
UniChem Connectivity Search for chemical match using the InChIKey VXVNSDXGZQXERO-NXDMJTDOSA-N