CHEBI:43602 - obeticholic acid

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ChEBI Name obeticholic acid
ChEBI ID CHEBI:43602
Definition A dihydroxy-5β-cholanic acid that is chenodeoxycholic acid carrying an additional ethyl substituent at the 6α-position. A semi-synthetic bile acid which acts as a farnesoid X receptor agonist and is used for treatment of primary biliary cholangitis.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:41467, CHEBI:43599, CHEBI:132971
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Formula C26H44O4
Net Charge 0
Average Mass 420.626
Monoisotopic Mass 420.32396
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
InChIKey ZXERDUOLZKYMJM-ZWECCWDJSA-N
SMILES C1[C@@]2([C@]3(CC[C@]4([C@]([C@@]3([C@@H]([C@@H]([C@@]2(C[C@@H](C1)O)[H])CC)O)[H])(CC[C@@]4([C@@H](CCC(O)=O)C)[H])[H])C)[H])C
Roles Classification
Biological Role(s): farnesoid X receptor agonist
An agonist that binds to and activates farnesoid X receptors
Application(s): hepatoprotective agent
Any compound that is able to prevent damage to the liver.
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ChEBI Ontology
Outgoing obeticholic acid (CHEBI:43602) has functional parent chenodeoxycholic acid (CHEBI:16755)
obeticholic acid (CHEBI:43602) has role farnesoid X receptor agonist (CHEBI:132972)
obeticholic acid (CHEBI:43602) has role hepatoprotective agent (CHEBI:62868)
obeticholic acid (CHEBI:43602) is a 3α-hydroxy steroid (CHEBI:36835)
obeticholic acid (CHEBI:43602) is a 7α-hydroxy steroid (CHEBI:36843)
obeticholic acid (CHEBI:43602) is a dihydroxy-5β-cholanic acid (CHEBI:23775)
IUPAC Name
6α-ethyl-3α,7α-dihydroxy-5β-cholan-24-oic acid
INN Source
obeticholic acid ChemIDplus
Synonyms Sources
(3α,5β,6α,7α)-6-ethyl-3,7-dihydroxycholan-24-oic acid IUPAC
6-ECDCA KEGG COMPOUND
6-Ethyl-CDCA KEGG COMPOUND
6-Ethylchenodeoxycholic acid ChemIDplus
6alpha-Ethyl-chenodeoxycholic acid KEGG COMPOUND
6α-ethylchenodeoxycholic acid ChEBI
INT 747 ChemIDplus
INT-747 ChemIDplus
INT747 ChemIDplus
Brand Name Source
Ocaliva KEGG DRUG
Manual Xrefs Databases
5155 DrugCentral
C15636 KEGG COMPOUND
CHC PDBeChem
D09360 KEGG DRUG
Obeticholic_acid Wikipedia
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Registry Numbers Types Sources
459789-99-2 CAS Registry Number ChemIDplus
9238543 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
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Last Modified
22 February 2017