CHEBI:16325 - lithocholic acid

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ChEBI Name lithocholic acid
ChEBI ID CHEBI:16325
Definition A monohydroxy-5β-cholanic acid with a α-hydroxy substituent at position 3. It is a bile acid obtained from chenodeoxycholic acid by bacterial action.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:1711, CHEBI:20238, CHEBI:20239
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Formula C24H40O3
Net Charge 0
Average Mass 376.57260
Monoisotopic Mass 376.29775
InChI InChI=1S/C24H40O3/c1-15(4-9-22(26)27)19-7-8-20-18-6-5-16-14-17(25)10-12-23(16,2)21(18)11-13-24(19,20)3/h15-21,25H,4-14H2,1-3H3,(H,26,27)/t15-,16-,17-,18+,19-,20+,21+,23+,24-/m1/s1
InChIKey SMEROWZSTRWXGI-HVATVPOCSA-N
SMILES [H][C@]12CC[C@]3([H])[C@]([H])(CC[C@]4(C)[C@]([H])(CC[C@@]34[H])[C@H](C)CCC(O)=O)[C@@]1(C)CC[C@@H](O)C2
Metabolite of Species Details
Mus musculus (NCBI:txid10090) See: PubMed
Homo sapiens (NCBI:txid9606) 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).
Application(s): geroprotector
Any compound that supports healthy aging, slows the biological aging process, or extends lifespan.
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ChEBI Ontology
Outgoing lithocholic acid (CHEBI:16325) has role geroprotector (CHEBI:176497)
lithocholic acid (CHEBI:16325) has role human metabolite (CHEBI:77746)
lithocholic acid (CHEBI:16325) has role mouse metabolite (CHEBI:75771)
lithocholic acid (CHEBI:16325) is a bile acid (CHEBI:3098)
lithocholic acid (CHEBI:16325) is a C24-steroid (CHEBI:131620)
lithocholic acid (CHEBI:16325) is a monohydroxy-5β-cholanic acid (CHEBI:36260)
lithocholic acid (CHEBI:16325) is conjugate acid of lithocholate (CHEBI:29744)
Incoming 7,12-dioxolithocholic acid (CHEBI:138389) has functional parent lithocholic acid (CHEBI:16325)
7-oxolithocholic acid (CHEBI:82679) has functional parent lithocholic acid (CHEBI:16325)
glycolithocholic acid (CHEBI:37998) has functional parent lithocholic acid (CHEBI:16325)
lithocholic acid 24-O-(β-D-glucuronide) (CHEBI:137807) has functional parent lithocholic acid (CHEBI:16325)
lithocholic acid 3-O-(β-D-glucuronide) (CHEBI:137921) has functional parent lithocholic acid (CHEBI:16325)
lithocholic acid sulfate (CHEBI:35421) has functional parent lithocholic acid (CHEBI:16325)
lithocholyl-CoA (CHEBI:87769) has functional parent lithocholic acid (CHEBI:16325)
taurolithocholic acid (CHEBI:36259) has functional parent lithocholic acid (CHEBI:16325)
lithocholic acid-2,2,4,4-d4 (CHEBI:192785) is a lithocholic acid (CHEBI:16325)
lithocholate (CHEBI:29744) is conjugate base of lithocholic acid (CHEBI:16325)
IUPAC Name
3α-hydroxy-5β-cholan-24-oic acid
Synonyms Sources
(3α,5β)-3-hydroxycholan-24-oic acid ChemIDplus
3alpha-Hydroxy-5beta-cholanate KEGG COMPOUND
3alpha-Hydroxy-5beta-cholanic acid KEGG COMPOUND
3α-hydroxy-5β-cholanic acid NIST Chemistry WebBook
3α-hydroxy-5β-cholanoic acid NIST Chemistry WebBook
5β-cholanic acid-3α-ol NIST Chemistry WebBook
Lithocholic acid KEGG COMPOUND
Manual Xrefs Databases
4OA PDBeChem
C03990 KEGG COMPOUND
CPD-7235 MetaCyc
HMDB0000761 HMDB
Lithocholic_acid Wikipedia
LMST04010003 LIPID MAPS
LSM-5371 LINCS
View more database links
Registry Numbers Types Sources
3217757 Reaxys Registry Number Reaxys
3217757 Beilstein Registry Number ChemIDplus
434-13-9 CAS Registry Number NIST Chemistry WebBook
434-13-9 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
20622262 PubMed citation Europe PMC
23639599 PubMed citation Europe PMC
24270587 PubMed citation Europe PMC
24332653 PubMed citation Europe PMC
24399466 PubMed citation Europe PMC
7068113 PubMed citation Europe PMC
Last Modified
26 October 2021