CHEBI:145219 - bisnorcholic acid

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ChEBI Name bisnorcholic acid
ChEBI ID CHEBI:145219
Definition A bile acid that is 24-dinor-5β-cholan-22-oic acid bearing three hydroxy substituents at positions 3α, 7α and 12α.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Mark Williams
Supplier Information
Download Molfile XML SDF
Formula C22H36O5
Net Charge 0
Average Mass 380.525
Monoisotopic Mass 380.25627
InChI InChI=1S/C22H36O5/c1-11(20(26)27)14-4-5-15-19-16(10-18(25)22(14,15)3)21(2)7-6-13(23)8-12(21)9-17(19)24/h11-19,23-25H,4-10H2,1-3H3,(H,26,27)/t11-,12-,13+,14+,15-,16-,17+,18-,19-,21-,22+/m0/s1
InChIKey BBSJMECOWBMUCF-XPCRKILGSA-N
SMILES [C@]12(CC[C@H](C[C@]2(C[C@H]([C@]3([C@]4([C@]([C@H](C[C@]13[H])O)([C@](CC4)([C@@H](C(=O)O)C)[H])C)[H])[H])O)[H])O)C
Metabolite of Species Details
Homo sapiens (NCBI:txid9606) Found in urine (BTO:0001419). Identified in urine of patients with cerebrotendinous xanthomatosis. See: PubMed
Homo sapiens (NCBI:txid9606) Found in blood serum (BTO:0000133). Identified in blood serum of patients with myasthenia gravis. See: DOI
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.
human blood serum metabolite
Any metabolite (endogenous or exogenous) found in human blood serum samples.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing bisnorcholic acid (CHEBI:145219) has role human blood serum metabolite (CHEBI:85234)
bisnorcholic acid (CHEBI:145219) has role human urinary metabolite (CHEBI:84087)
bisnorcholic acid (CHEBI:145219) is a 12α-hydroxy steroid (CHEBI:36846)
bisnorcholic acid (CHEBI:145219) is a 3α-hydroxy steroid (CHEBI:36835)
bisnorcholic acid (CHEBI:145219) is a 7α-hydroxy steroid (CHEBI:36843)
bisnorcholic acid (CHEBI:145219) is a bile acid (CHEBI:3098)
IUPAC Name
(2S)-2-[(1R,3aS,3bR,4R,5aS,7R,9aS,9bS,11S,11aS)-4,7,11-trihydroxy-9a,11a-dimethyl-hexadecahydro-1H-cyclopenta[a]phenanthren-1-yl]propanoic acid
Synonyms Sources
24-dinor-3α,7α,12α-trihydroxy-5β-cholan-22-oic acid LIPID MAPS
dinorcholic acid LIPID MAPS
Manual Xrefs Databases
FDB022836 FooDB
HMDB0002082 HMDB
LMST04050005 LIPID MAPS
View more database links
Citations Waiting for Citations Types Sources
2079611 PubMed citation Europe PMC
22838635 PubMed citation Europe PMC
3559381 PubMed citation Europe PMC
Last Modified
12 November 2019