CHEBI:16359 - cholic acid

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ChEBI Name cholic acid
ChEBI ID CHEBI:16359
Definition A bile acid that is 5β-cholan-24-oic acid bearing three α-hydroxy substituents at position 3, 7 and 12.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:1694, CHEBI:20223, CHEBI:41494, CHEBI:23210, CHEBI:29077
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Formula C24H40O5
Net Charge 0
Average Mass 408.57140
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-OELDTZBJSA-N
SMILES [H][C@@]12C[C@H](O)CC[C@]1(C)[C@@]1([H])C[C@H](O)[C@]3(C)[C@]([H])(CC[C@@]3([H])[C@]1([H])[C@H](O)C2)[C@H](C)CCC(O)=O
Metabolite of Species Details
Mus musculus (NCBI:10090) See: DOI
Mus musculus (NCBI:10090) Source: BioModels - MODEL1507180067 See: PubMed
Homo sapiens (NCBI:9606) See: PubMed
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 metabolite
Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
mouse metabolite
Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
View more via ChEBI Ontology
ChEBI Ontology
Outgoing cholic acid (CHEBI:16359) has role human metabolite (CHEBI:77746)
cholic acid (CHEBI:16359) has role mouse metabolite (CHEBI:75771)
cholic acid (CHEBI:16359) is a bile acid (CHEBI:3098)
cholic acid (CHEBI:16359) is a C24-steroid (CHEBI:131620)
cholic acid (CHEBI:16359) is a trihydroxy-5β-cholanic acid (CHEBI:27114)
cholic acid (CHEBI:16359) is conjugate acid of cholate (CHEBI:29747)
Incoming (23S)-methyl-3α,7α,12α-trihydroxy-5β-cholan-24-oic acid (CHEBI:488147) has functional parent cholic acid (CHEBI:16359)
3-[(3-cholamidopropyl)dimethylammonio]propane-1-sulfonate (CHEBI:1418) has functional parent cholic acid (CHEBI:16359)
N-(2-phosphonoethyl)cholamide (CHEBI:1019) has functional parent cholic acid (CHEBI:16359)
S-choloyl-4ʼ-phosphopantetheine (CHEBI:132321) has functional parent cholic acid (CHEBI:16359)
cholate salt (CHEBI:23169) has functional parent cholic acid (CHEBI:16359)
choloyl-CoA (CHEBI:15519) has functional parent cholic acid (CHEBI:16359)
glycochenodeoxycholic acid 7-sulfate (CHEBI:52031) has functional parent cholic acid (CHEBI:16359)
glycocholic acid (CHEBI:17687) has functional parent cholic acid (CHEBI:16359)
hyodeoxycholic acid (CHEBI:52023) has functional parent cholic acid (CHEBI:16359)
murideoxycholic acid (CHEBI:52030) has functional parent cholic acid (CHEBI:16359)
taurocholic acid (CHEBI:28865) has functional parent cholic acid (CHEBI:16359)
taurohyocholic acid (CHEBI:52022) has functional parent cholic acid (CHEBI:16359)
cholate (CHEBI:29747) is conjugate base of cholic acid (CHEBI:16359)
IUPAC Name
3α,7α,12α-trihydroxy-5β-cholan-24-oic acid
Synonyms Sources
(3α,5β,7α,12α)-3,7,12-trihydroxycholan-24-oic acid NIST Chemistry WebBook
3alpha,7alpha,12alpha-Trihydroxy-5beta-cholanate KEGG COMPOUND
3alpha,7alpha,12alpha-Trihydroxy-5beta-cholanic acid KEGG COMPOUND
3α,7α,12α-trihydroxy-5β-cholanic acid NIST Chemistry WebBook
CHOLIC ACID PDBeChem
Cholic acid KEGG COMPOUND
Cholsäure ChEBI
Database Links Databases
C00695 KEGG COMPOUND
CHD PDBeChem
CHOLATE MetaCyc
Cholic_Acid Wikipedia
DB02659 DrugBank
HMDB00619 HMDB
LMST04010001 LIPID MAPS
LSM-5541 LINCS
View more database links
Registry Numbers Types Sources
2822009 Beilstein Registry Number ChemIDplus
2822009 Reaxys Registry Number Reaxys
81-25-4 CAS Registry Number ChemIDplus
81-25-4 CAS Registry Number NIST Chemistry WebBook
Citation Waiting for Citations Type Source
22770225 PubMed citation CiteXplore
Last Modified
29 June 2016