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> Main
CHEBI:16325 - lithocholic acid
Main
ChEBI Ontology
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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
Supplier Information
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Wikipedia
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Read full article at Wikipedia
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 (Br
o
nsted 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.
View more via ChEBI Ontology
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
C
24
-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
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