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> Main
CHEBI:145219 - bisnorcholic acid
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ChEBI Name
bisnorcholic acid
ChEBI ID
CHEBI:145219
Definition
A bile acid that is 24-dinor-5β-cholan-22-oic acid bearing three hydroxy substituents at positions 3α, 7α and 12α.
Stars
This entity has been manually annotated by the ChEBI Team.
Submitter
Mark Williams
Supplier Information
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Molfile
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Formula
C22H36O5
Net Charge
0
Average Mass
380.525
Monoisotopic Mass
380.25627
InChI
InChI=1S/C22H36O5/c1-
11(20(26)
27)
14-
4-
5-
15-
19-
16(10-
18(25)
22(14,15)
3)
21(2)
7-
6-
13(23)
8-
12(21)
9-
17(19)
24/h11-
19,23-
25H,4-
10H2,1-
3H3,(H,26,27)
/t11-
,12-
,13+,14+,15-
,16-
,17+,18-
,19-
,21-
,22+/m0/s1
InChIKey
BBSJMECOWBMUCF-XPCRKILGSA-N
SMILES
[C@]
12(CC[C@H]
(C[C@]
2(C[C@H]
([C@]
3([C@]
4([C@]
([C@H]
(C[C@]
13[H]
)
O)
([C@]
(CC4)
([C@@H]
(C(=O)
O)
C)
[H]
)
C)
[H]
)
[H]
)
O)
[H]
)
O)
C
Metabolite of Species
Details
Homo sapiens
(NCBI:txid9606)
Found in urine
(BTO:0001419)
. Identified in urine of patients with cerebrotendinous xanthomatosis. See:
PubMed
Homo sapiens
(NCBI:txid9606)
Found in blood serum
(BTO:0000133)
. Identified in blood serum of patients with myasthenia gravis. See:
DOI
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.
human blood serum metabolite
Any metabolite (endogenous or exogenous) found in human blood serum samples.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing
bisnorcholic acid (
CHEBI:145219
)
has role
human blood serum metabolite (
CHEBI:85234
)
bisnorcholic acid (
CHEBI:145219
)
has role
human urinary metabolite (
CHEBI:84087
)
bisnorcholic acid (
CHEBI:145219
)
is a
12α-hydroxy steroid (
CHEBI:36846
)
bisnorcholic acid (
CHEBI:145219
)
is a
3α-hydroxy steroid (
CHEBI:36835
)
bisnorcholic acid (
CHEBI:145219
)
is a
7α-hydroxy steroid (
CHEBI:36843
)
bisnorcholic acid (
CHEBI:145219
)
is a
bile acid (
CHEBI:3098
)
IUPAC Name
(2
S
)-
2-
[(1
R
,3a
S
,3b
R
,4
R
,5a
S
,7
R
,9a
S
,9b
S
,11
S
,11a
S
)-
4,7,11-
trihydroxy-
9a,11a-
dimethyl-
hexadecahydro-
1
H
-
cyclopenta[
a
]phenanthren-
1-
yl]propanoic acid
Synonyms
Sources
24-dinor-3α,7α,12α-trihydroxy-5β-cholan-22-oic acid
LIPID MAPS
dinorcholic acid
LIPID MAPS
Manual Xrefs
Databases
FDB022836
FooDB
HMDB0002082
HMDB
LMST04050005
LIPID MAPS
View more database links
Citations
Types
Sources
2079611
PubMed citation
Europe PMC
22838635
PubMed citation
Europe PMC
3559381
PubMed citation
Europe PMC
Last Modified
12 November 2019