CHEBI:9907 - ursodeoxycholic acid

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ChEBI Name ursodeoxycholic acid
ChEBI ID CHEBI:9907
Definition A bile acid found in the bile of bears (Ursidae) as a conjugate with taurine. Used therapeutically, it prevents the synthesis and absorption of cholesterol and can lead to the dissolution of gallstones.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C24H40O4
Net Charge 0
Average Mass 392.57200
Monoisotopic Mass 392.293
InChI InChI=1S/C24H40O4/c1-14(4-7-21(27)28)17-5-6-18-22-19(9-11-24(17,18)3)23(2)10-8-16(25)12-15(23)13-20(22)26/h14-20,22,25-26H,4-13H2,1-3H3,(H,27,28)/t14-,15+,16-,17-,18+,19+,20+,22+,23+,24-/m1/s1
InChIKey RUDATBOHQWOJDD-UZVSRGJWSA-N
SMILES [H][C@@]12C[C@H](O)CC[C@]1(C)[C@@]1([H])CC[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: 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).
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ChEBI Ontology
Outgoing ursodeoxycholic acid (CHEBI:9907) has role human metabolite (CHEBI:77746)
ursodeoxycholic acid (CHEBI:9907) has role mouse metabolite (CHEBI:75771)
ursodeoxycholic acid (CHEBI:9907) is a bile acid (CHEBI:3098)
ursodeoxycholic acid (CHEBI:9907) is a C24-steroid (CHEBI:131620)
ursodeoxycholic acid (CHEBI:9907) is a dihydroxy-5β-cholanic acid (CHEBI:23775)
ursodeoxycholic acid (CHEBI:9907) is conjugate acid of ursodeoxycholate (CHEBI:78604)
Incoming 3α,7β-dihydroxy-12-oxo-5β-cholanic acid (CHEBI:138401) has functional parent ursodeoxycholic acid (CHEBI:9907)
glycoursodeoxycholic acid (CHEBI:89929) has functional parent ursodeoxycholic acid (CHEBI:9907)
tauroursodeoxycholic acid (CHEBI:80774) has functional parent ursodeoxycholic acid (CHEBI:9907)
ursodeoxycholoyl-CoA (CHEBI:138379) has functional parent ursodeoxycholic acid (CHEBI:9907)
ursodeoxycholate (CHEBI:78604) is conjugate base of ursodeoxycholic acid (CHEBI:9907)
IUPAC Name
3α,7β-dihydroxy-5β-cholan-24-oic acid
Synonyms Sources
(3α,5β,7β)-3,7-dihydroxycholan-24-oic acid ChemIDplus
3alpha,7beta-Dihydroxy-5beta-cholan-24-oic acid KEGG COMPOUND
Actigall ChemIDplus
Ursodeoxycholate KEGG COMPOUND
Ursodeoxycholic acid KEGG COMPOUND
Ursodiol KEGG COMPOUND
Database Links Databases
2797 DrugCentral
C07880 KEGG COMPOUND
D00734 KEGG DRUG
DB01586 DrugBank
HMDB0000946 HMDB
LMST04010033 LIPID MAPS
LSM-6555 LINCS
Ursodiol Wikipedia
View more database links
Registry Numbers Types Sources
128-13-2 CAS Registry Number KEGG COMPOUND
128-13-2 CAS Registry Number ChemIDplus
3219888 Reaxys Registry Number Reaxys
3219888 Beilstein Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
14989050 PubMed citation Europe PMC
17489439 PubMed citation Europe PMC
24816727 PubMed citation Europe PMC
Last Modified
07 September 2017