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ChEBI
> Main
CHEBI:81240 - ursocholic acid
Main
ChEBI Ontology
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ChEBI Name
ursocholic acid
ChEBI ID
CHEBI:81240
Definition
A bile acid that is 5β-cholan-24-oic acid bearing three hydroxy substituents at positions 3α, 7β and 12α.
Stars
This entity has been manually annotated by the ChEBI Team.
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Formula
C24H40O5
Net Charge
0
Average Mass
408.572
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-UTLSPDKDSA-N
SMILES
C1[C@@]
2([C@]
3(C[C@@H]
([C@]
4([C@]
([C@@]
3([C@H]
(C[C@@]
2(C[C@@H]
(C1)
O)
[H]
)
O)
[H]
)
(CC[C@@]
4([C@@H]
(CCC(O)
=O)
C)
[H]
)
[H]
)
C)
O)
[H]
)
C
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 urinary metabolite
Any metabolite (endogenous or exogenous) found in human urine samples.
EC 1.1.1.159 (7alpha-hydroxysteroid dehydrogenase) inhibitor
An EC 1.1.1.* (oxidoreductase acting on donor CH-OH group, NAD+ or NADP+ acceptor) inhibitor that interferes with the action of 7
alpha
-hydroxysteroid dehydrogenase (EC 1.1.1.159).
View more via ChEBI Ontology
ChEBI Ontology
Outgoing
ursocholic acid (
CHEBI:81240
)
has role
EC 1.1.1.159 (7α-hydroxysteroid dehydrogenase) inhibitor (
CHEBI:138390
)
ursocholic acid (
CHEBI:81240
)
has role
human urinary metabolite (
CHEBI:84087
)
ursocholic acid (
CHEBI:81240
)
is a
12α-hydroxy steroid (
CHEBI:36846
)
ursocholic acid (
CHEBI:81240
)
is a
3α-hydroxy steroid (
CHEBI:36835
)
ursocholic acid (
CHEBI:81240
)
is a
7β-hydroxy steroid (
CHEBI:35349
)
ursocholic acid (
CHEBI:81240
)
is a
bile acid (
CHEBI:3098
)
ursocholic acid (
CHEBI:81240
)
is a
C
24
-steroid (
CHEBI:131620
)
ursocholic acid (
CHEBI:81240
)
is a
trihydroxy-5β-cholanic acid (
CHEBI:27114
)
ursocholic acid (
CHEBI:81240
)
is conjugate acid of
ursocholate (
CHEBI:137880
)
Incoming
tauroursocholic acid (
CHEBI:145227
)
has functional parent
ursocholic acid (
CHEBI:81240
)
ursocholate (
CHEBI:137880
)
is conjugate base of
ursocholic acid (
CHEBI:81240
)
IUPAC Name
3α,7β,12α-trihydroxy-5β-cholan-24-oic acid
Synonyms
Sources
(3α,5β,7β,12α)-3,7,12-trihydroxycholan-24-oic acid
IUPAC
3alpha,7beta,12alpha-Trihydroxy-5beta-cholan-24-oic acid
ChemIDplus
3alpha,7beta,12alpha-Trihydroxy-5beta-cholanic acid
KEGG COMPOUND
7-Epicholic acid
KEGG COMPOUND
Manual Xrefs
Databases
C17644
KEGG COMPOUND
HMDB0000917
HMDB
View more database links
Registry Numbers
Types
Sources
2955-27-3
CAS Registry Number
ChemIDplus
5303401
Reaxys Registry Number
Reaxys
Citations
Types
Sources
10216137
PubMed citation
Europe PMC
12401785
PubMed citation
Europe PMC
1551642
PubMed citation
Europe PMC
1943496
PubMed citation
Europe PMC
2079611
PubMed citation
Europe PMC
22198717
PubMed citation
Europe PMC
2396085
PubMed citation
Europe PMC
24076126
PubMed citation
Europe PMC
26718089
PubMed citation
Europe PMC
28751127
PubMed citation
Europe PMC
3660436
PubMed citation
Europe PMC
3715370
PubMed citation
Europe PMC
3949116
PubMed citation
Europe PMC
7676478
PubMed citation
Europe PMC
8500738
PubMed citation
Europe PMC
9177526
PubMed citation
Europe PMC
Last Modified
24 February 2020