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> Main
CHEBI:132472 - 18-hydroxylinoleic acid
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ChEBI Name
18-hydroxylinoleic acid
ChEBI ID
CHEBI:132472
Definition
An ω-hydroxy fatty acid that is linoleic acid in which one of the terminal methyl hydrogens has been replaced by a hydroxy group.
Stars
This entity has been manually annotated by the ChEBI Team.
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Formula
C18H32O3
Net Charge
0
Average Mass
296.446
Monoisotopic Mass
296.23514
InChI
InChI=1S/C18H32O3/c19-
17-
15-
13-
11-
9-
7-
5-
3-
1-
2-
4-
6-
8-
10-
12-
14-
16-
18(20)
21/h1-
2,5,7,19H,3-
4,6,8-
17H2,(H,20,21)
/b2-
1-
,7-
5-
InChIKey
KPBOLLJJMHIJPH-PQZOIKATSA-N
SMILES
C(=C\C/C=C\CCCCCO)\CCCCCCCC(=O)O
Metabolite of Species
Details
Neurospora crassa
(NCBI:txid5141)
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):
fungal metabolite
Any eukaryotic metabolite produced during a metabolic reaction in fungi, the kingdom that includes microorganisms such as the yeasts and moulds.
human xenobiotic metabolite
Any human metabolite produced by metabolism of a xenobiotic compound in humans.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing
18-hydroxylinoleic acid (
CHEBI:132472
)
has functional parent
linoleic acid (
CHEBI:17351
)
18-hydroxylinoleic acid (
CHEBI:132472
)
has role
fungal metabolite (
CHEBI:76946
)
18-hydroxylinoleic acid (
CHEBI:132472
)
has role
human xenobiotic metabolite (
CHEBI:76967
)
18-hydroxylinoleic acid (
CHEBI:132472
)
is a
ω-hydroxy-long-chain fatty acid (
CHEBI:140997
)
18-hydroxylinoleic acid (
CHEBI:132472
)
is a
polyunsaturated fatty acid (
CHEBI:26208
)
18-hydroxylinoleic acid (
CHEBI:132472
)
is conjugate acid of
18-hydroxylinoleate (
CHEBI:132029
)
Incoming
18-hydroxylinoleate (
CHEBI:132029
)
is conjugate base of
18-hydroxylinoleic acid (
CHEBI:132472
)
IUPAC Name
(9
Z
,12
Z
)-18-hydroxyoctadeca-9,12-dienoic acid
Synonyms
Sources
18-HODE
ChEBI
18-hydroxy-(9
Z
,12
Z
)-octadecadienoic acid
ChEBI
ω-hydroxylinoleic acid
ChEBI
Manual Xref
Database
CPD-17376
MetaCyc
View more database links
Registry Number
Type
Source
14940271
Reaxys Registry Number
Reaxys
Citations
Types
Sources
10553002
PubMed citation
Europe PMC
26859959
PubMed citation
Europe PMC
8806734
PubMed citation
Europe PMC
Last Modified
24 January 2023