obeticholic acid   Click here for help

GtoPdb Ligand ID: 3435

Synonyms: 6-ECDCA | 6-Et CDCA | 6-ethylchenodeoxycholic acid | INT-747 | OCA | Ocaliva®
Approved drug PDB Ligand
obeticholic acid is an approved drug (EMA & FDA (2016))
Compound class: Synthetic organic
Comment: Obeticholic acid is a semisynthetic bile acid analogue. It acts as a farnesoid X receptor (FXR) agonist.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 4
Hydrogen bond donors 3
Rotatable bonds 5
Topological polar surface area 77.76
Molecular weight 420.32
XLogP 7.04
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
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Canonical SMILES CCC1C(O)C2C3CCC(C3(C)CCC2C2(C1CC(O)CC2)C)C(CCC(=O)O)C
Isomeric SMILES CC[C@H]1[C@@H](O)[C@H]2[C@@H]3CC[C@@H]([C@@]3(C)CC[C@@H]2[C@@]2([C@H]1C[C@H](O)CC2)C)[C@@H](CCC(=O)O)C
InChI InChI=1S/C26H44O4/c1-5-17-21-14-16(27)10-12-26(21,4)20-11-13-25(3)18(15(2)6-9-22(28)29)7-8-19(25)23(20)24(17)30/h15-21,23-24,27,30H,5-14H2,1-4H3,(H,28,29)/t15-,16-,17-,18-,19+,20+,21+,23+,24-,25-,26-/m1/s1
InChI Key ZXERDUOLZKYMJM-ZWECCWDJSA-N
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (EMA & FDA (2016))
IUPAC Name Click here for help
(4R)-4-[(3R,5S,6R,7R,8S,9S,10S,13R,14S,17R)-6-ethyl-3,7-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoic acid
International Nonproprietary Names Click here for help
INN number INN
9084 obeticholic acid
Synonyms Click here for help
6-ECDCA | 6-Et CDCA | 6-ethylchenodeoxycholic acid | INT-747 | OCA | Ocaliva®
Database Links Click here for help
CAS Registry No. 459789-99-2
ChEMBL Ligand CHEMBL566315
DrugCentral Ligand 5155
GtoPdb PubChem SID 178100437
PubChem CID 447715
RCSB PDB Ligand CHC
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Wikipedia Obeticholic_acid