Molecule: (4Z,8E,10Z,12E,14S,16Z,19Z)-14-hydroperoxydocosahexaenoic acid

A hydroperoxy fatty acid that is (4Z,8E,10Z,12E,16Z,19Z)-docosahexaenoic acid in which the hydroperoxy group is located at position 14S. An intermediate of specialised proresolving mediators
Synonyms for (4Z,8E,10Z,12E,14S,16Z,19Z)-14-hydroperoxydocosahexaenoic acid :
14(S)-HpDHA
14(S)-hydroperoxydocosahexaenoic acid
Molecular Formula: C22H32O4
Molecular wt: 360.488 g/mole
Charge: 0
SMILES: OC(CC/C=C\CC/C=C/C=C\C=C\[C@H](C/C=C\C/C=C\CC)OO)=O
InChIKey: QEAQJVYOZNBPLR-KSJZJIFISA-N
InChI=1S/C22H32O4/c1-2-3-4-5-12-15-18-21(26-25)19-16-13-10-8-6-7-9-11-14-17-20-22(23)24/h3-4,6,8,10-16,19,21,25H,2,5,7,9,17-18,20H2,1H3,(H,23,24)/b4-3-,8-6+,13-10-,14-11-,15-12-,19-16+/t21-/m0/s1
CHEBI:140220
Sample reactions for this molecule:
ALOX12:Fe2+ oxidises DHA to 14(S)-Hp-DHA
ALOX12:Fe2+ dehydrogenates 14(S)-Hp-DHA to 13(S),14(S)-epoxy-DHA
ALOX5 oxidises 14(S)-Hp-DHA to 7(S),14(S)-diHp-DHA
ALOX12:Fe2+ dehydrogenates 14(S)-Hp-DPAn-3 to 13,14-epoxy-DPAn-3
Hydroperoxy reducatase reduces 14(S)-Hp-DHA to 14(S)-HDHA