CHEBI:48905 - (9Z,11E,13S,15Z)-13-hydroperoxyoctadeca-9,11,15-trienoic acid

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name (9Z,11E,13S,15Z)-13-hydroperoxyoctadeca-9,11,15-trienoic acid
ChEBI ID CHEBI:48905
ChEBI ASCII Name (9Z,11E,13S,15Z)-13-hydroperoxyoctadeca-9,11,15-trienoic acid
Definition A lipid hydroperoxide, obtained by the formal substitution of a hydrogen at position 9 of (9Z,11E,15Z)-octadeca-9,11,15-trienoic acid by a hydroperoxy group (the 13S-stereoisomer). Biochemically, it is an 18-C rearrangement and primary peroxidation product of α-linolenic acid, an intermediate in prostaglandin and leukotriene metabolism, and the substrate of the lyase enzyme hydroperoxide dehydratase.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C18H30O4
Net Charge 0
Average Mass 310.42840
Monoisotopic Mass 310.21441
InChI InChI=1S/C18H30O4/c1-2-3-11-14-17(22-21)15-12-9-7-5-4-6-8-10-13-16-18(19)20/h3,7,9,11-12,15,17,21H,2,4-6,8,10,13-14,16H2,1H3,(H,19,20)/b9-7-,11-3-,15-12+/t17-/m0/s1
InChIKey UYQGVDXDXBAABN-FQSPHKRJSA-N
SMILES CC\C=C/C[C@H](OO)\C=C\C=C/CCCCCCCC(O)=O
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing (9Z,11E,13S,15Z)-13-hydroperoxyoctadeca-9,11,15-trienoic acid (CHEBI:48905) has functional parent (9Z,11E,15Z)-octadeca-9,11,15-trienoic acid (CHEBI:48907)
(9Z,11E,13S,15Z)-13-hydroperoxyoctadeca-9,11,15-trienoic acid (CHEBI:48905) is a hydroperoxyoctadecatrienoic acid (CHEBI:134615)
(9Z,11E,13S,15Z)-13-hydroperoxyoctadeca-9,11,15-trienoic acid (CHEBI:48905) is a trienoic fatty acid (CHEBI:73155)
(9Z,11E,13S,15Z)-13-hydroperoxyoctadeca-9,11,15-trienoic acid (CHEBI:48905) is conjugate acid of (9Z,11E,13S,15Z)-13-hydroperoxyoctadeca-9,11,15-trienoate (CHEBI:58757)
(9Z,11E,13S,15Z)-13-hydroperoxyoctadeca-9,11,15-trienoic acid (CHEBI:48905) is enantiomer of (9Z,11E,13R,15Z)-13-hydroperoxyoctadecatrienoic acid (CHEBI:133986)
Incoming (9Z,11E,13S,15Z)-13-hydroperoxyoctadeca-9,11,15-trienoate (CHEBI:58757) is conjugate base of (9Z,11E,13S,15Z)-13-hydroperoxyoctadeca-9,11,15-trienoic acid (CHEBI:48905)
(9Z,11E,13R,15Z)-13-hydroperoxyoctadecatrienoic acid (CHEBI:133986) is enantiomer of (9Z,11E,13S,15Z)-13-hydroperoxyoctadeca-9,11,15-trienoic acid (CHEBI:48905)
IUPAC Name
(9Z,11E,13S,15Z)-13-hydroperoxyoctadeca-9,11,15-trienoic acid
Synonyms Sources
(9Z,11E,15Z)-(13S)-13-Hydroperoxyoctadeca-9,11,15-trienoic acid KEGG COMPOUND
(9Z,11E,15Z)-(13S)-Hydroperoxyoctadeca-9,11,15-trienoate KEGG COMPOUND
13(S)-HPOT ChEBI
13(S)-HpOTrE KEGG COMPOUND
13(S)-hydroperoxy-9(Z),11(E),15(Z)-octadecatrienoic acid ChEBI
13(S)-hydroperoxylinolenic acid MetaCyc
13-HPOT MetaCyc
13-HPOT KEGG COMPOUND
13S-HpOTrE LIPID MAPS
13S-hydroperoxy-9(Z),11(E),15(Z)-octadecatrienoic acid MetaCyc
13S-hydroperoxy-9Z,11E,15Z-octadecatrienoic acid LIPID MAPS
Manual Xrefs Databases
C04785 KEGG COMPOUND
CPD-725 MetaCyc
LMFA02000052 LIPID MAPS
View more database links
Registry Numbers Types Sources
4188888 Reaxys Registry Number Reaxys
4188888 Beilstein Registry Number Beilstein
Citation Waiting for Citations Type Source
7893744 PubMed citation Europe PMC
Last Modified
25 August 2020