LIPID MAPS

Structure Database (LMSD)

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Common Name

(+/-)-18-HEPE

Systematic Name

(+/-)-18-hydroxy-5Z,8Z,11Z,14Z,16E-eicosapentaenoic acid

Synonyms

LM ID

LMFA03070033

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

(±)18-HEPE is produced by non-enzymatic oxidation of eicosapentaenoic acid (EPA).¹ 18-HEPE levels are increased in the plasma and heart, as well as in the supernatant of cultured peritoneal macrophages isolated from fat-1 transgenic mice that are capable of endogenously producing ω-3 fatty acids from ω-6 fatty acids.^2,3,4 It reduces increases in cardiac fibrosis and the expression of Nppa, Col1a1, Tgfb1, Cx3cl1, and Adgre1 induced by transverse aortic constriction in a mouse model of cardiac hypertrophy when administered at doses of 1 and 5 µg.³

This information has been provided by Cayman Chemical

References

1. Li, J., Chen, C.-Y., Arita, M., et al. An omega-3 polyunsaturated fatty acid derivative, 18-HEPE, protects against CXCR4-associated melanoma metastasis. Carcinogenesis 39(11), 1380-1388 (2018).

2. Endo, J., Sano, M., Isobe, Y., et al. 18-HEPE, an n-3 fatty acid metabolite released by macrophages, prevents pressure overload-induced maladaptive cardiac remodeling. J. Exp. Med. 211(8), 1673-1687 (2014).

3. Kang, J.X. Fat-1 transgenic mice: A new model for omega-3 research. Prostaglandins Leukot. Essent. Fatty Acids 77(5-6), 263-267 (2007).

4. Onodera, T., Fukuhara, A., Shin, J., et al. Eicosapentaenoic acid and 5-HEPE enhance macrophage-mediated Treg induction in mice. Sci. Rep. 7(1), 4560 (2017).

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)

LRWYBGFSVUBWMO-UXNZXXPISA-N

InChi (Click to copy)

InChI=1S/C20H30O3/c1-2-19(21)17-15-13-11-9-7-5-3-4-6-8-10-12-14-16-18-20(22)23/h4-7,10-13,15,17,19,21H,2-3,8-9,14,16,18H2,1H3,(H,22,23)/b6-4-,7-5-,12-10-,13-11-,17-15+

SMILES (Click to copy)

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