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

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

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ChEBI ID	CHEBI:48905
ChEBI Name	(9Z,11E,13S,15Z)-13-hydroperoxyoctadeca-9,11,15-trienoic acid
Stars
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.
Last Modified	22 February 2023
Submitter	Kirill Degtyarenko
Downloads	Molfile

Formula	C18H30O4
Net Charge	0
Average Mass	310.434
Monoisotopic Mass	310.21441
SMILES	CC/C=C\C[C@@H](/C=C/C=C\CCCCCCCC(=O)O)OO
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

Roles Classification

Bronsted acid A molecular entity capable of donating a hydron to an acceptor (Brønsted base).

ChEBI Ontology

Outgoing Relation(s)
	(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 Relation(s)
	(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	Source
13(S)-hydroperoxy-9(Z),11(E),15(Z)-octadecatrienoic acid	ChEBI
13(S)-HPOT	ChEBI
13S-HpOTrE	LIPID MAPS
13S-hydroperoxy-9Z,11E,15Z-octadecatrienoic acid	LIPID MAPS
13(S)-hydroperoxylinolenic acid	MetaCyc
13S-hydroperoxy-9(Z),11(E),15(Z)-octadecatrienoic acid	MetaCyc

Manual Xrefs	Databases
LMFA02000052	LIPID MAPS
C04785	KEGG COMPOUND

Registry Numbers	Sources
Reaxys:4188888	Reaxys

Citations