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
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Registry Numbers Types Sources
3217757 Reaxys Registry Number Reaxys
434-13-9 CAS Registry Number NIST Chemistry WebBook
434-13-9 CAS Registry Number ChemIDplus
Citations Waiting for Citations
Last Modified
26 October 2021