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> Main
CHEBI:16359 - cholic acid
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ChEBI Name
cholic acid
ChEBI ID
CHEBI:16359
Definition
A bile acid that is 5β-cholan-24-oic acid bearing three α-hydroxy substituents at position 3, 7 and 12.
Stars
This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs
CHEBI:1694, CHEBI:20223, CHEBI:41494, CHEBI:23210, CHEBI:29077
Supplier Information
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Molfile
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Wikipedia
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Read full article at Wikipedia
Formula
C24H40O5
Net Charge
0
Average Mass
408.57140
Monoisotopic Mass
408.28757
InChI
InChI=1S/C24H40O5/c1-
13(4-
7-
21(28)
29)
16-
5-
6-
17-
22-
18(12-
20(27)
24(16,17)
3)
23(2)
9-
8-
15(25)
10-
14(23)
11-
19(22)
26/h13-
20,22,25-
27H,4-
12H2,1-
3H3,(H,28,29)
/t13-
,14+,15-
,16-
,17+,18+,19-
,20+,22+,23+,24-
/m1/s1
InChIKey
BHQCQFFYRZLCQQ-OELDTZBJSA-N
SMILES
[H]
[C@@]
12C[C@H]
(O)
CC[C@]
1(C)
[C@@]
1([H]
)
C[C@H]
(O)
[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:txid10090)
See:
DOI
Mus musculus
(NCBI:txid10090)
Source: BioModels - MODEL1507180067 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
).
View more via ChEBI Ontology
ChEBI Ontology
Outgoing
cholic acid (
CHEBI:16359
)
has role
human metabolite (
CHEBI:77746
)
cholic acid (
CHEBI:16359
)
has role
mouse metabolite (
CHEBI:75771
)
cholic acid (
CHEBI:16359
)
is a
12α-hydroxy steroid (
CHEBI:36846
)
cholic acid (
CHEBI:16359
)
is a
3α-hydroxy steroid (
CHEBI:36835
)
cholic acid (
CHEBI:16359
)
is a
7α-hydroxy steroid (
CHEBI:36843
)
cholic acid (
CHEBI:16359
)
is a
bile acid (
CHEBI:3098
)
cholic acid (
CHEBI:16359
)
is a
C
24
-steroid (
CHEBI:131620
)
cholic acid (
CHEBI:16359
)
is a
trihydroxy-5β-cholanic acid (
CHEBI:27114
)
cholic acid (
CHEBI:16359
)
is conjugate acid of
cholate (
CHEBI:29747
)
Incoming
(23
S
)-methyl-3α,7α,12α-trihydroxy-5β-cholan-24-oic acid (
CHEBI:488147
)
has functional parent
cholic acid (
CHEBI:16359
)
3-[(3-cholamidopropyl)dimethylammonio]propane-1-sulfonate (
CHEBI:1418
)
has functional parent
cholic acid (
CHEBI:16359
)
N
-(2-phosphonoethyl)cholamide (
CHEBI:1019
)
has functional parent
cholic acid (
CHEBI:16359
)
S
-choloyl-4ʼ-phosphopantetheine (
CHEBI:132321
)
has functional parent
cholic acid (
CHEBI:16359
)
cholate salt (
CHEBI:23169
)
has functional parent
cholic acid (
CHEBI:16359
)
cholic acid 24-
O
-(β-
D
-glucuronide) (
CHEBI:137791
)
has functional parent
cholic acid (
CHEBI:16359
)
choloyl-CoA (
CHEBI:15519
)
has functional parent
cholic acid (
CHEBI:16359
)
glycochenodeoxycholic acid 7-sulfate (
CHEBI:52031
)
has functional parent
cholic acid (
CHEBI:16359
)
glycocholic acid (
CHEBI:17687
)
has functional parent
cholic acid (
CHEBI:16359
)
hyodeoxycholic acid (
CHEBI:52023
)
has functional parent
cholic acid (
CHEBI:16359
)
murideoxycholic acid (
CHEBI:52030
)
has functional parent
cholic acid (
CHEBI:16359
)
taurocholic acid (
CHEBI:28865
)
has functional parent
cholic acid (
CHEBI:16359
)
taurohyocholic acid (
CHEBI:52022
)
has functional parent
cholic acid (
CHEBI:16359
)
cholate (
CHEBI:29747
)
is conjugate base of
cholic acid (
CHEBI:16359
)
IUPAC Name
3α,7α,12α-trihydroxy-5β-cholan-24-oic acid
Synonyms
Sources
(3α,5β,7α,12α)-3,7,12-trihydroxycholan-24-oic acid
NIST Chemistry WebBook
3alpha,7alpha,12alpha-Trihydroxy-5beta-cholanate
KEGG COMPOUND
3alpha,7alpha,12alpha-Trihydroxy-5beta-cholanic acid
KEGG COMPOUND
3α,7α,12α-trihydroxy-5β-cholanic acid
NIST Chemistry WebBook
CHOLIC ACID
PDBeChem
Cholic acid
KEGG COMPOUND
Cholsäure
ChEBI
Manual Xrefs
Databases
3096
DrugCentral
C00695
KEGG COMPOUND
CHD
PDBeChem
CHOLATE
MetaCyc
Cholic_Acid
Wikipedia
DB02659
DrugBank
HMDB0000619
HMDB
LMST04010001
LIPID MAPS
LSM-5541
LINCS
View more database links
Registry Numbers
Types
Sources
2822009
Reaxys Registry Number
Reaxys
81-25-4
CAS Registry Number
ChemIDplus
81-25-4
CAS Registry Number
NIST Chemistry WebBook
Citation
Type
Source
22770225
PubMed citation
Europe PMC
Last Modified
01 September 2017