LIPID MAPS

Structure Database (LMSD)

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Common Name

(+/-)-5-HEPE

Systematic Name

(+/-)-5-hydroxy-6E,8Z,11Z,14Z,17Z-eicosapentaenoic acid

Synonyms

LM ID

LMFA03070027

Formula

C₂₀H₃₀O₃

Exact Mass

Calculate m/z

318.219495

Sum Composition

FA 20:5;O

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

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Classification

Biological Context

(±)5-HEPE is produced by non-enzymatic oxidation of EPA. It contains equal amounts of 5(S)-HEPE and 5(R)-HEPE. The biological activity of (±)5-HEPE is likely mediated by one of the individual isomers, most commonly the 5(S) isomer in mammalian systems. EPA can be metabolized to 5-HEPE in human and bovine neutrophils, and human eosinophils, which is further metabolized to 5-oxoEPE and LTB5.1,2,3 The 5-series metabolites of EPA, namely 5-HEPE, 5-oxoEPE, and LTB5, have significantly decreased biological effects compared to the arachidonic acid-derived metabolites.³

This information has been provided by Cayman Chemical

References

1. Taylor, S.M., Laegreid, W.W., Heidel, J.R., et al. EArachidonic and eicosapentaenoic acid metabolism in bovine neutrophils and platelets: Effect of calcium ionophore. J. Leukoc. Biol. 42, 253-262 (1987).

2. Lee, T.H., Mencia-Huerta, J.M., Shih, C., et al. Effects of exogenous arachidonic, eicosapentaenoic, and docosahexaenoic acids on the generation of 5-lipoxygenase pathway products by ionophore-activated human neutrophils. J. Clin. Invest. 74, 1922-1933 (1984).

3. Powell, W.S., Gravel, S., and Gravelle, F. Formation of a 5-oxo metabolite of 5,8,11,14,17-eicosapentaenoic acid and its effects on human neutrophils and eosinophils. J. Lipid Res. 36, 2590-2598 (1995).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Homo sapiens (#9606)

Mammalia (#40674)

Lipidomics reveals a remarkable diversity of lipids in human plasma,
J Lipid Res, 2010

Pubmed ID: 20671299

DOI: 10.1194/jlr.M009449

String Representations

InChiKey (Click to copy)

FTAGQROYQYQRHF-FCWZHQICSA-N

InChi (Click to copy)

InChI=1S/C20H30O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-16-19(21)17-15-18-20(22)23/h3-4,6-7,9-10,12-14,16,19,21H,2,5,8,11,15,17-18H2,1H3,(H,22,23)/b4-3-,7-6-,10-9-,13-12-,16-14+

SMILES (Click to copy)

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