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CHEBI:16359 - cholic acid

ChEBI IDCHEBI:16359
ChEBI Namecholic acid
Stars
DefinitionA bile acid that is 5β-cholan-24-oic acid bearing three α-hydroxy substituents at position 3, 7 and 12.
Secondary ChEBI IDsCHEBI:1694, CHEBI:20223, CHEBI:23210, CHEBI:29077, CHEBI:41494
Last Modified17 June 2025
DownloadsMolfile
FormulaC24H40O5
Net Charge0
Average Mass408.579
Monoisotopic Mass408.28757
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@H](C)CCC(=O)O)[C@]1([H])[C@H](O)C2
InChIInChI=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
InChIKeyBHQCQFFYRZLCQQ-OELDTZBJSA-N
Wikipedia
Species of MetaboliteComponentSourceComments
Homo sapiens (ncbitaxon:9606) - PubMed (11316487)
Mus musculus (ncbitaxon:10090)
- DOI (10.1172/JCI16309)
- PubMed (19425150) Source: BioModels - MODEL1507180067
Roles Classification
Chemical Role:
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Roles:
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).
ChEBI Ontology
Outgoing Relation(s)
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 12α-hydroxy steroid (CHEBI:36846)
cholic acid (CHEBI:16359) is a 3α-hydroxy steroid (CHEBI:36835)
cholic acid (CHEBI:16359) is a 7α-hydroxy steroid (CHEBI:36843)
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 Relation(s)
(23S)-methyl-3α,7α,12α-trihydroxy-5β-cholan-24-oic acid (CHEBI:488147) has functional parent cholic acid (CHEBI:16359)
N-(2-phosphonoethyl)cholamide (CHEBI:1019) has functional parent cholic acid (CHEBI:16359)
S-choloyl-4'-phosphopantetheine (CHEBI:132321) has functional parent cholic acid (CHEBI:16359)
3-[(3-cholamidopropyl)dimethylammonio]propane-1-sulfonate (CHEBI:1418) has functional parent cholic acid (CHEBI:16359)
cholate salt (CHEBI:23169) has functional parent cholic acid (CHEBI:16359)
cholic acid 24-O-(β-D-glucuronide) (CHEBI:137791) has functional parent cholic acid (CHEBI:16359)
Cholic acid sulfate (CHEBI:233476) has functional parent cholic acid (CHEBI:16359)
choloyl-CoA (CHEBI:15519) has functional parent cholic acid (CHEBI:16359)
cholyl-L-tryptophan (CHEBI:232263) 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)
cholate (CHEBI:29747) is conjugate base of cholic acid (CHEBI:16359)
IUPAC Name 
3α,7α,12α-trihydroxy-5β-cholan-24-oic acid
Synonyms  Source
3alpha,7alpha,12alpha-Trihydroxy-5beta-cholanic acidKEGG COMPOUND
Cholic acidKEGG COMPOUND
CHOLIC ACIDPDBeChem
(3α,5β,7α,12α)-3,7,12-trihydroxycholan-24-oic acidNIST Chemistry WebBook
CholsäureChEBI
3α,7α,12α-trihydroxy-5β-cholanic acidNIST Chemistry WebBook
Manual XrefsDatabases
C00695KEGG COMPOUND
CHDPDBeChem
LMST04010001LIPID MAPS
Cholic_AcidWikipedia
DB02659DrugBank
CHOLATEMetaCyc
HMDB0000619HMDB
LSM-5541LINCS
3096DrugCentral
Registry NumbersSources
Reaxys:2822009Reaxys
CAS:81-25-4KEGG COMPOUND
CAS:81-25-4ChemIDplus
CAS:81-25-4NIST Chemistry WebBook
Citations