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Structure Database (LMSD)

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Common Name

N-(5Z,8Z,11Z,14Z,17Z-eicosapentaenoyl-EA

Systematic Name

N-(5Z,8Z,11Z,14Z,17Z-eicosapentaenoyl)-ethanolamine

Synonyms

N-cis-5,8, 11,14,17-eicosapentaenoylethanolamine
Timnodonoyl-EA

LM ID

LMFA08040008

Formula

C₂₂H₃₅NO₂

Exact Mass

Calculate m/z

345.266779

Sum Composition

NAE 20:5

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

View NP-MRD ID(NMR) spectrum

Classification

Biological Context

Eicosapentaenoyl ethanolamide (EPEA) is an N-acylethanolamide that inhibits dietary-restriction-induced lifespan extension in wild type and TOR pathway mutant nematodes.¹ Produced endogenously from eicosapentaenoic acid, EPEA serves as a metabolic signal that couples nutrient availability with growth and lifespan. EPEA also has anti-inflammatory properties, suppressing the expression of IL-6 and MCP-1 in 3T3-L1 adipocytes in response to lipopolysaccharide.²

This information has been provided by Cayman Chemical

References

1. Balvers, M.G., Verhoeckx, K.C., Plastina, P., et al. Docosahexaenoic acid and eicosapentaenoic acid are converted by 3T3-L1 adipocytes to N-acyl ethanolamines with anti-inflammatory properties. Biochim. Biophys. Acta 1801(10), 1107-1114 (2010).

2. Lucanic, M., Held, J.M., Vantipalli, M.C., et al. N-acylethanolamine signalling mediates the effect of diet on lifespan in Caenorhabditis elegans. Nature 473(7346), 226-229 (2011).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Mus musculus (#10090)

Mammalia (#40674)

Docosahexaenoic acid and eicosapentaenoic acid are converted by 3T3-L1 adipocytes to N-acyl ethanolamines with anti-inflammatory properties.,
Biochim Biophys Acta, 2010

Pubmed ID: 20601112

String Representations

InChiKey (Click to copy)

OVKKNJPJQKTXIT-JLNKQSITSA-N

InChi (Click to copy)

InChI=1S/C22H35NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-22(25)23-20-21-24/h3-4,6-7,9-10,12-13,15-16,24H,2,5,8,11,14,17-21H2,1H3,(H,23,25)/b4-3-,7-6-,10-9-,13-12-,16-15-

SMILES (Click to copy)

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