venetoclax   

GtoPdb Ligand ID: 8318

Synonyms: ABT-199 | GDC-0199 | Venclexta® | Venclyxto®
venetoclax is an approved drug (FDA and EMA (2016))
Compound class: Synthetic organic
Comment: Venetoclax is a BH3 mimetic that selectively targets Bcl-2 [4], 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 [1].
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 9
Hydrogen bond donors 3
Rotatable bonds 14
Topological polar surface area 180.41
Molecular weight 867.32
XLogP 9.38
No. Lipinski's rules broken 2
SMILES / InChI / InChIKey
Canonical SMILES Clc1ccc(cc1)C1=C(CCC(C1)(C)C)CN1CCN(CC1)c1ccc(c(c1)Oc1cnc2c(c1)cc[nH]2)C(=O)NS(=O)(=O)c1ccc(c(c1)[N+](=O)[O-])NCC1CCOCC1
Isomeric SMILES Clc1ccc(cc1)C1=C(CCC(C1)(C)C)CN1CCN(CC1)c1ccc(c(c1)Oc1cnc2c(c1)cc[nH]2)C(=O)NS(=O)(=O)c1ccc(c(c1)[N+](=O)[O-])NCC1CCOCC1
InChI InChI=1S/C45H50ClN7O7S/c1-45(2)15-11-33(39(26-45)31-3-5-34(46)6-4-31)29-51-17-19-52(20-18-51)35-7-9-38(42(24-35)60-36-23-32-12-16-47-43(32)49-28-36)44(54)50-61(57,58)37-8-10-40(41(25-37)53(55)56)48-27-30-13-21-59-22-14-30/h3-10,12,16,23-25,28,30,48H,11,13-15,17-22,26-27,29H2,1-2H3,(H,47,49)(H,50,54)
InChI Key LQBVNQSMGBZMKD-UHFFFAOYSA-N
Classification
Compound class Synthetic organic
Approved drug? Yes (FDA and EMA (2016))
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
International Nonproprietary Names
INN number INN
9925 venetoclax
Synonyms
ABT-199 | GDC-0199 | Venclexta® | Venclyxto®
Database Links
CAS Registry No. 1257044-40-8
ChEMBL Ligand CHEMBL3137309
DrugCentral Ligand 5133
GtoPdb PubChem SID 252166530
PubChem CID 49846579
RCSB PDB Ligand LBM
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Search UniChem for chemical match using the InChIKey LQBVNQSMGBZMKD-UHFFFAOYSA-N
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Tocris
ABT 199
Cat. No. 6960