abiraterone   

GtoPdb Ligand ID: 6745

Compound class: Synthetic organic
Comment: Abiraterone is the active from of the abiraterone acetate prodrug.
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2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 2
Hydrogen bond donors 1
Rotatable bonds 1
Topological polar surface area 33.12
Molecular weight 349.24
XLogP 5.54
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
Canonical SMILES OC1CCC2(C(=CCC3C2CCC2(C3CC=C2c2cccnc2)C)C1)C
Isomeric SMILES O[C@H]1CC[C@]2(C(=CC[C@@H]3[C@@H]2CC[C@]2([C@H]3CC=C2c2cccnc2)C)C1)C
InChI 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
InChI Key GZOSMCIZMLWJML-VJLLXTKPSA-N
Classification
Compound class Synthetic organic
Prodrug abiraterone acetate
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
International Nonproprietary Names
INN number INN
7375 abiraterone
Database Links
CAS Registry No. 154229-19-3 (source: Scifinder)
ChEBI CHEBI:68642
ChEMBL Ligand CHEMBL254328
DrugBank Ligand DB05812
GtoPdb PubChem SID 178103356
PubChem CID 132971
RCSB PDB Ligand AER
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SynPHARM 78807 (in complex with CYP17A1)