LIPID MAPS

Structure Database (LMSD)

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Common Name

5S-HEPE

Systematic Name

5S-hydroxy-6E,8Z,11Z,14Z,17Z-eicosapentaenoic acid

Synonyms

LM ID

LMFA03070010

Formula

C₂₀H₃₀O₃

Exact Mass

Calculate m/z

318.219496

Sum Composition

FA 20:5;O

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

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View studies deposited in Metabolomics Workbench in which this molecule has been identified

Classification

Biological Context

5(S)-HEPE is an active metabolite of eicosapentaenoic acid (EPA).¹ It is formed from EPA by 5-lipoxygenase (5-LO). 5(S)-HEPE is an agonist of G protein-coupled receptor 119 (GPR119).² It increases cAMP accumulation in CHO-K1 cells expressing human GPR119 when used at a concentration of 10 µM. 5(S)-HEPE increases glucose-induced insulin secretion from MING6 insulinoma pancreatic islets and glucagon-like peptide 1 (GLP-1) secretion from HuTu 80 adenocarcinoma cells when used at a concentration of 10 µM. Serum levels of 5(S)-HEPE are elevated in patients with hyperlipidemia.³

This information has been provided by Cayman Chemical

References

1. Noguchi, N., Yoshida, Y., Kaneda, H., et al. Action of ebselen as an antioxidant against lipid peroxidation. Biochem. Pharmacol. 44(1), 39-44 (1992).

2. Kogure, R., Toyama, K., Kiyamuta, S., et al. 5-Hydroxy-eicosapentaenoic acid is an endogenous GPR119 agonist and enhances glucose-dependent insulin secretion. Biochem. Biophys. Res. Commun. 416(1-2), 58-63 (2011).

3. Schuchardt, J.P., Schmidt, S., Kressel, G., et al. Comparison of free serum oxylipin concentrations in hyper- vs. normolipidemic men. Prostaglandins Leukot. Essent. Fatty Acids 89(1), 19-29 (2013).

String Representations

InChiKey (Click to copy)

FTAGQROYQYQRHF-GHWNLOBHSA-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+/t19-/m1/s1

SMILES (Click to copy)

C(/C/C=C\C/C=C\C/C=C\CC)=C/C=C/[C@@H](O)CCCC(=O)O