Marvin  03180817412D          

 22 21  0  0  1  0            999 V2000
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  1  0  0  0  0
  2  1  2  0  0  0  0
  3  2  1  0  0  0  0
  3 18  1  0  0  0  0
  3  4  1  1  0  0  0
  4  5  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
M  END
> <ID>
CHEBI:48905

> <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.

> <STAR>
3

> <SYNONYM>
13S-hydroperoxy-9Z,11E,15Z-octadecatrienoic acid; 13S-hydroperoxy-9(Z),11(E),15(Z)-octadecatrienoic acid; 13S-HpOTrE; 13-HPOT; 13-HPOT; 13(S)-hydroperoxylinolenic acid; 13(S)-hydroperoxy-9(Z),11(E),15(Z)-octadecatrienoic acid; 13(S)-HpOTrE; 13(S)-HPOT; (9Z,11E,15Z)-(13S)-Hydroperoxyoctadeca-9,11,15-trienoate; (9Z,11E,15Z)-(13S)-13-Hydroperoxyoctadeca-9,11,15-trienoic acid

> <IUPAC_NAME>
(9Z,11E,13S,15Z)-13-hydroperoxyoctadeca-9,11,15-trienoic acid

> <FORMULA>
C18H30O4

> <MASS>
310.42840

> <MONOISOTOPIC_MASS>
310.21441

> <CHARGE>
0

> <SMILES>
CC\C=C/C[C@H](OO)\C=C\C=C/CCCCCCCC(O)=O

> <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

> <REAXYS_REGISTRY_NUMBER>
4188888

> <KEGG_COMPOUND_ACCESSION>
C04785

> <LIPID_MAPS_INSTANCE_ACCESSION>
LMFA02000052

> <PUBMED_CITATION>
35088946; 7893744

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