Molecule: 5(S)-hydroperoxy-18(R)-hydroxy-(6E,8Z,11Z,14Z,16E)-icosapentaenoic acid

A polyunsaturated fatty acid that is (6E,8Z,11Z,14Z,16E)-icosapentaenoic acid substituted at positions 5 and 18 by hydroperoxy and hydroxy groups respectively (the 5S, 18R-stereoisomer).
Synonyms for 5(S)-hydroperoxy-18(R)-hydroxy-(6E,8Z,11Z,14Z,16E)-icosapentaenoic acid :
(5S)-hydroperoxy-(18R)-hydroxy-(6E,8Z,11Z,14Z,16E)-eicosapentaenoic acid
(5S)-hydroperoxy-(18R)-hydroxy-(6E,8Z,11Z,14Z,16E)-icosapentaenoic acid
18(R)-hydroxy-5(S)-HpEPE
5(S)-Hp-18(R)-HEPE
5(S)-hydroperoxy-18(R)-hydroxy-(6E,8Z,11Z,14Z,16E)-eicosapentaenoic acid
Molecular Formula: C20H30O5
Molecular wt: 350.450 g/mole
Charge: 0
SMILES: [C@H](CCCC(O)=O)(/C=C/C=C\C/C=C\C\C=C/C=C/[C@@H](CC)O)OO
InChIKey: JIOJPWROWDJRKM-NNQKPOSRSA-N
InChI=1S/C20H30O5/c1-2-18(21)14-11-9-7-5-3-4-6-8-10-12-15-19(25-24)16-13-17-20(22)23/h3-4,7-12,14-15,18-19,21,24H,2,5-6,13,16-17H2,1H3,(H,22,23)/b4-3-,9-7-,10-8-,14-11+,15-12+/t18-,19-/m1/s1
CHEBI:132908
Sample reactions for this molecule:
ALOX5 oxidises 18(R)-HEPE to 5(S)-Hp-18(R)-HEPE
ALOX5 oxidises 5(S)-Hp-18(R)-HEPE to 5S,6S-epoxy-18(R)-HEPE
5-HEDH dehydrogenates 5(S)-Hp-18(R)-HpEPE to 18(R)-RvE2