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DT2216   Click here for help

GtoPdb Ligand ID: 11722

Synonyms: DT-2216
Compound class: Synthetic organic
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 [2,4]. In vivo (in mice), The target protein binding moiety is based on the BCL-XL protein antagonist navitoclax (ABT-263) [2]. Since VHL is poorly expressed in platelets, DT2216 is significantly less toxic to platelets than parental navitoclax.

DT2216 is commercially available from our sponsors

2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 20
Hydrogen bond donors 5
Rotatable bonds 35
Topological polar surface area 321.37
Molecular weight 1540.58
XLogP 13.54
No. Lipinski's rules broken 3

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES O[C@H]1CN([C@@H](C1)C(=O)N[C@H](c1ccc(cc1)c1scnc1C)C)C(=O)[C@H](C(C)(C)C)NC(=O)CCCCCC(=O)N1CCN(CC1)CC[C@@H](Nc1ccc(cc1S(=O)(=O)C(F)(F)F)S(=O)(=O)NC(=O)c1ccc(cc1)N1CCN(CC1)CC1=C(CCC(C1)(C)C)c1ccc(cc1)Cl)CSc1ccccc1
Isomeric SMILES Cc1c(scn1)c1ccc(cc1)[C@H](C)NC(=O)[C@@H]1C[C@H](CN1C(=O)[C@H](C(C)(C)C)NC(=O)CCCCCC(=O)N1CCN(CC1)CC[C@H](CSc1ccccc1)Nc1c(cc(cc1)S(=O)(=O)NC(=O)c1ccc(cc1)N1CCN(CC1)CC1=C(CCC(C1)(C)C)c1ccc(cc1)Cl)S(=O)(=O)C(F)(F)F)O
InChI InChI=1S/C77H96ClF3N10O10S4/c1-51(53-18-20-55(21-19-53)70-52(2)82-50-103-70)83-73(96)66-44-61(92)48-91(66)74(97)71(75(3,4)5)85-68(93)16-12-9-13-17-69(94)90-42-36-87(37-43-90)35-33-59(49-102-62-14-10-8-11-15-62)84-65-31-30-63(45-67(65)104(98,99)77(79,80)81)105(100,101)86-72(95)56-24-28-60(29-25-56)89-40-38-88(39-41-89)47-57-46-76(6,7)34-32-64(57)54-22-26-58(78)27-23-54/h8,10-11,14-15,18-31,45,50-51,59,61,66,71,84,92H,9,12-13,16-17,32-44,46-49H2,1-7H3,(H,83,96)(H,85,93)(H,86,95)/t51-,59+,61+,66-,71+/m0/s1
InChI Key PXVFFBGSTYQHRO-REQIQPEASA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Classification Click here for help
Compound class Synthetic organic
Ligand families/groups PROTACs, molecular glues and other degraders
IUPAC Name Click here for help
(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
Synonyms Click here for help
DT-2216
Database Links Click here for help
GtoPdb PubChem SID 458923757
PubChem CID 139331475
Search Google for chemical match using the InChIKey PXVFFBGSTYQHRO-REQIQPEASA-N
Search Google for chemicals with the same backbone PXVFFBGSTYQHRO
UniChem Compound Search for chemical match using the InChIKey PXVFFBGSTYQHRO-REQIQPEASA-N
UniChem Connectivity Search for chemical match using the InChIKey PXVFFBGSTYQHRO-REQIQPEASA-N

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MedChemExpress
DT2216 (links to external site)
Cat. No. HY-130604