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.
2D Structure
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Physico-chemical Properties
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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
SMILES / InChI / InChIKey
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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
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
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