LIPID MAPS

Structure Database (LMSD)

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Common Name

20-HEPE

Systematic Name

20-hydroxy-(5Z,8Z,11Z,14Z,17Z)-eicosapentaenoic acid

Synonyms

20-hydroxy-(5Z,8Z,11Z,14Z,17Z)-Icosapentaenoic acid

LM ID

LMFA01050603

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

View spectra on LIPID MAPS Standard Spectra DB

Classification

Biological Context

20-HEPE is a metabolite of eicosapentaenoic acid (EPA) that is formed via ω-oxidation of EPA by cytochrome P450 (CYP) ω-oxidases, including human CYP4F3B.¹ It activates peroxisome proliferator-activated receptor α (PPARα) in COS-7 cells expressing a luciferase reporter when used at a concentration of 10 μM. 20-HEPE also activates murine transient receptor potential vanilloid receptor 1 (mTRPV1) in vitro but lacks antinociceptive activity in rats.²

This information has been provided by Cayman Chemical

References

1. Harmon, S.D., Fang, X., Kaduce, T.L., et al. Oxygenation of ω-3 fatty acids by human cytochrome P450 4F3B: Effect on 20-hydroxyeicosatetraenoic acid production. Prostaglandins Leukot. Essent. Fatty Acids 75(3), 169-177 (2006).

2. Hwang, S.H., Wagner, H., Xu, J., et al. Chemical synthesis and biological evaluation of ω-hydroxy polyunsaturated fatty acids. Bioorg. Med. Chem. Lett. 27(3), 620-625 (2017).

Reactions

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References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Homo sapiens (#9606)

Mammalia (#40674)

Oxygenation of omega-3 fatty acids by human cytochrome P450 4F3B: effect on 20-hydroxyeicosatetraenoic acid production.,
Prostaglandins Leukot Essent Fatty Acids, 2006

Pubmed ID: 16820285

String Representations

InChiKey (Click to copy)

PPMOWWAALQWWLJ-NUKMUHRASA-N

InChi (Click to copy)

InChI=1S/C20H30O3/c21-19-17-15-13-11-9-7-5-3-1-2-4-6-8-10-12-14-16-18-20(22)23/h1,3-4,6-7,9-10,12-13,15,21H,2,5,8,11,14,16-19H2,(H,22,23)/b3-1-,6-4-,9-7-,12-10-,15-13-

SMILES (Click to copy)

OC(=O)CCC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCO