Obeticholic Acid
(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
Molecular Identity
Obeticholic Acid
(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
PubChem CID: 447715
Obeticholic acid is a dihydroxy-5beta-cholanic acid that is chenodeoxycholic acid carrying an additional ethyl substituent at the 6alpha-position. A semi-synthetic bile acid which acts as a farnesoid X receptor agonist and is used for treatment of primary biliary cholangitis. It has a role as a farnesoid X receptor agonist and a hepatoprotective agent. It is a dihydroxy-5beta-cholanic acid, a 3alpha-hydroxy steroid and a 7alpha-hydroxy steroid. It is functionally related to a chenodeoxycholic acid.
2D Structure
Properties
C26H44O4
Molecular Formula
420.60
Molecular Weight
g/mol
420.3240
Exact Mass
Da
5.7
XLogP
Above Lipinski threshold
77.8
TPSA
Good oral absorption (< 140 A²)
3
H-Bond Donors
4
H-Bond Acceptors
649
Complexity
SMILES
Canonical SMILES
SMILES: CCC1C2CC(CCC2(C3CCC4(C(C3C1O)CCC4C(C)CCC(=O)O)C)C)OIsomeric SMILES
SMILES: CC[C@@H]1[C@@H]2C[C@@H](CC[C@@]2([C@H]3CC[C@]4([C@H]([C@@H]3[C@@H]1O)CC[C@@H]4[C@H](C)CCC(=O)O)C)C)OSynonyms(20)
Obeticholic acid459789-99-26-ECDCAINT-7476-Ethylchenodeoxycholic acidOcaliva6-Ethyl-CDCADSP-1747INT747acido obeticolicoacide obeticholiqueINT 7476alpha-ethylchenodeoxycholic acidDSP17470462Z4S4OZ
Data from PubChem (NCBI)
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Drug Network
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