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CHEBI:43602 - obeticholic acid

ChEBI IDCHEBI:43602
ChEBI Nameobeticholic acid
Stars
DefinitionA 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.
Secondary ChEBI IDsCHEBI:41467, CHEBI:43599, CHEBI:132971
Last Modified22 February 2017
SubmitterSteve
DownloadsMolfile
FormulaC26H44O4
Net Charge0
Average Mass420.634
Monoisotopic Mass420.32396
SMILES[H][C@@]12CC[C@]([H])([C@H](C)CCC(=O)O)[C@@]1(C)CC[C@]1([H])[C@@]3(C)CC[C@@H](O)C[C@@]3([H])[C@@H](CC)[C@@H](O)[C@@]21[H]
InChIInChI=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
InChIKeyZXERDUOLZKYMJM-ZWECCWDJSA-N
Wikipedia
Roles Classification
Biological Role:
farnesoid X receptor agonist  An agonist that binds to and activates farnesoid X receptors
Application:
hepatoprotective agent  Any compound that is able to prevent damage to the liver.
ChEBI Ontology
Outgoing Relation(s)
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 acidChemIDplus
Synonyms  Source
6-Ethyl-CDCAKEGG COMPOUND
6-ECDCAKEGG COMPOUND
6alpha-Ethyl-chenodeoxycholic acidKEGG COMPOUND
INT-747ChemIDplus
6-Ethylchenodeoxycholic acidChemIDplus
INT747ChemIDplus
Brand Name  Source
OcalivaKEGG DRUG
Manual XrefsDatabases
C15636KEGG COMPOUND
D09360KEGG DRUG
CHCPDBeChem
Obeticholic_acidWikipedia
5155DrugCentral
Registry NumbersSources
Reaxys:9238543Reaxys
CAS:459789-99-2KEGG COMPOUND
CAS:459789-99-2ChemIDplus
Citations