CHEBI:81240 - ursocholic acid

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ChEBI Name ursocholic acid
ChEBI ID CHEBI:81240
Definition A bile acid that is 5β-cholan-24-oic acid bearing three hydroxy substituents at positions 3α, 7β and 12α.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C24H40O5
Net Charge 0
Average Mass 408.572
Monoisotopic Mass 408.288
InChI InChI=1S/C24H40O5/c1-13(4-7-21(28)29)16-5-6-17-22-18(12-20(27)24(16,17)3)23(2)9-8-15(25)10-14(23)11-19(22)26/h13-20,22,25-27H,4-12H2,1-3H3,(H,28,29)/t13-,14+,15-,16-,17+,18+,19+,20+,22+,23+,24-/m1/s1
InChIKey BHQCQFFYRZLCQQ-UTLSPDKDSA-N
SMILES C1[C@@]2([C@]3(C[C@@H]([C@]4([C@]([C@@]3([C@H](C[C@@]2(C[C@@H](C1)O)[H])O)[H])(CC[C@@]4([C@@H](CCC(O)=O)C)[H])[H])C)O)[H])C
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): human urinary metabolite
Any metabolite (endogenous or exogenous) found in human urine samples.
EC 1.1.1.159 (7alpha-hydroxysteroid dehydrogenase) inhibitor
An EC 1.1.1.* (oxidoreductase acting on donor CH-OH group, NAD+ or NADP+ acceptor) inhibitor that interferes with the action of 7alpha-hydroxysteroid dehydrogenase (EC 1.1.1.159).
View more via ChEBI Ontology
ChEBI Ontology
Outgoing ursocholic acid (CHEBI:81240) has role EC 1.1.1.159 (7α-hydroxysteroid dehydrogenase) inhibitor (CHEBI:138390)
ursocholic acid (CHEBI:81240) has role human urinary metabolite (CHEBI:84087)
ursocholic acid (CHEBI:81240) is a 12α-hydroxy steroid (CHEBI:36846)
ursocholic acid (CHEBI:81240) is a 3α-hydroxy steroid (CHEBI:36835)
ursocholic acid (CHEBI:81240) is a 7β-hydroxy steroid (CHEBI:35349)
ursocholic acid (CHEBI:81240) is a bile acid (CHEBI:3098)
ursocholic acid (CHEBI:81240) is a C24-steroid (CHEBI:131620)
ursocholic acid (CHEBI:81240) is a trihydroxy-5β-cholanic acid (CHEBI:27114)
ursocholic acid (CHEBI:81240) is conjugate acid of ursocholate (CHEBI:137880)
Incoming ursocholate (CHEBI:137880) is conjugate base of ursocholic acid (CHEBI:81240)
IUPAC Name
3α,7β,12α-trihydroxy-5β-cholan-24-oic acid
Synonyms Sources
(3α,5β,7β,12α)-3,7,12-trihydroxycholan-24-oic acid IUPAC
3alpha,7beta,12alpha-Trihydroxy-5beta-cholan-24-oic acid ChemIDplus
3alpha,7beta,12alpha-Trihydroxy-5beta-cholanic acid KEGG COMPOUND
7-Epicholic acid KEGG COMPOUND
Manual Xrefs Databases
C17644 KEGG COMPOUND
HMDB0000917 HMDB
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Registry Numbers Types Sources
2955-27-3 CAS Registry Number ChemIDplus
5303401 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
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Last Modified
06 September 2017