LIPID MAPS

Structure Database (LMSD)

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Common Name

13(14)-EpDPE

Systematic Name

(+/-)-13(14)-epoxy-4Z,7Z,10Z,16Z,19Z-docosapentaenoic acid

Synonyms

13,14-EpDPA
13,14-EpDPE

LM ID

LMFA04000036

Formula

C₂₂H₃₂O₃

Exact Mass

Calculate m/z

344.235146

Sum Composition

FA 22:6;O

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

View spectra on LIPID MAPS Standard Spectra DB

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

Classification

Biological Context

±)13(14)-EpDPA is a docosahexaenoic acid (DHA) epoxygenase metabolite, derived via epoxidation of the 13,14-double bond of DHA. It has been detected in rat brain and spinal cord and is a preferred substrate for soluble epoxide hydrolase with a Km value of 3.2 µM. (±)13(14)-EpDPA demonstrates antihyperalgesic activity in inflammatory and neuropathic pain models.¹ (±)13(14)-EpDPA and other epoxy metabolites of DHA are also reported to potently inhibit angiogenesis and tumor growth in in vitro assays.²

This information has been provided by Cayman Chemical

References

1. Morisseau, C., Inceoglu, B., Schmelzer, K., et al. Naturally occurring monoepoxides of eicosapentaenoic acid and docosahexaenoic acid are bioactive antihyperalgesic lipids. J. Lipid Res. 51, 3481-3490 (2010).

2. Zhang, G., Panigrahy, D., Mahakian, L.M., et al. Epoxy metabolites of docosahexaenoic acid (DHA) inhibit angiogenesis, tumor growth, and metastasis. Proc. Natl. Acad. Sci. USA 110(16), 6530-6535 (2013).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Rattus norvegicus (#10116)

Mammalia (#40674)

Naturally occurring monoepoxides of eicosapentaenoic acid and docosahexaenoic acid are bioactive antihyperalgesic lipids.,
J Lipid Res, 2010

Pubmed ID: 20664072

String Representations

InChiKey (Click to copy)

DCFKVKFLEPMEGT-UQZHZJRSSA-N

InChi (Click to copy)

InChI=1S/C22H32O3/c1-2-3-4-5-11-14-17-20-21(25-20)18-15-12-9-7-6-8-10-13-16-19-22(23)24/h3-4,6-7,10-15,20-21H,2,5,8-9,16-19H2,1H3,(H,23,24)/b4-3-,7-6-,13-10-,14-11-,15-12-

SMILES (Click to copy)

C(CC/C=C\C/C=C\C/C=C\CC1OC1C/C=C\C/C=C\CC)(=O)O