LIPID MAPS

Structure Database (LMSD)

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Common Name

(5Z,8Z,11Z,13E)-15-hydroperoxyeicosa-5,8,11,13-tetraenoic acid

Systematic Name

(5Z,8Z,11Z,13E)-15-hydroperoxyeicosa-5,8,11,13-tetraenoic acid

Synonyms

15-HPETE

LM ID

LMFA03060102

Formula

C₂₀H₃₂O₄

Exact Mass

Calculate m/z

336.23006

Sum Composition

FA 20:4;O2

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

Classification

Biological Context

15(S)-HpETE is a monohydroperoxy polyunsaturated fatty acid (PUFA) produced by the action of 15-lipoxygenase (15-LO) on arachidonic acid. It is either metabolized to 14,15-leukotriene A41 or reduced to 15(S)-HETE by peroxidases.^2,1 15(S)-HpETE mediates a number of biological functions including the induction of c-fos and c-jun, and activation of AP-1.3 15(S)-HpETE inhibits prostacyclin synthesis in porcine aortic microsomes and bovine endothelial cells, and can cause the suicide inactivation of porcine 12-LO.^2,4,5

This information has been provided by Cayman Chemical

References

1. Rao, G.N., Glasgow, W.C., Eling, T.E., et al. Role of hydroperoxyeicosatetraenoic acids in oxidative stress-induced activating protein 1 (AP-1) activity. J. Biol. Chem. 271, 27760-27764 (1996).

2. Kishimoto, K., Nakamura, M., Suzuki, H., et al. Suicide inactivation of porcine leukocyte 12-lipoxygenase associated with its incorporation of 15-hydroperoxy-5,8,11,13-eicosatetraenoic acid derivative. Biochim. Biophys. Acta 1300, 56-62 (1996).

3. Mayer, B., Moser, R., Gleispach, H., et al. Possible inhibitory function of endogenous 15-hydroperoxyeicosatetraenoic acid on prostacyclin formation in bovine aortic endothelial cells. Biochim. Biophys. Acta 875, 641-653 (1986).

4. Moncada, S., Gryglewski, R.J., Bunting, S., et al. A lipid peroxide inhibits the enzyme in blood vessel microsomes that generates from prostaglandin endoperoxides the substance (prostaglandin X) which prevents platelet aggregation. Prostaglandins 12, 715-737 (1976).

5. Bryant, R.W., Schewe, T., Rapoport, S.M., et al. Leukotriene formation by a purified reticulocyte lipoxygenase enzyme. Conversion of arachidonic acid and 15-hydroperoxyeicosatetraenoic acid to 14,15-leukotriene A4. J. Biol. Chem. 260(6), 3548-3555 (1985).

String Representations

InChiKey (Click to copy)

BFWYTORDSFIVKP-USWFWKISSA-N

InChi (Click to copy)

InChI=1S/C20H32O4/c1-2-3-13-16-19(24-23)17-14-11-9-7-5-4-6-8-10-12-15-18-20(21)22/h4-5,8-11,14,17,19,23H,2-3,6-7,12-13,15-16,18H2,1H3,(H,21,22)/b5-4-,10-8-,11-9-,17-14+

SMILES (Click to copy)

O(C(/C=C/C=C\C/C=C\C/C=C\CCCC(=O)O)CCCCC)O