LIPID MAPS

Structure Database (LMSD)

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Common Name

7(8)-EpDPE

Systematic Name

(+/-)-7(8)-epoxy-4Z,10Z,13Z,16Z,19Z-docosapentaenoic acid

Synonyms

(+/-)7(8)-EpDPA
(+/-)7,8-epoxy DPA

LM ID

LMFA04000034

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

(±)7(8)-EpDPA is an epoxide derivative of DHA that is generated by the action of cytochrome P450 epoxygenases.¹ It is naturally occurring in plasma and brain and spinal cord tissues and is increased following dietary supplementation with ω-3 fatty acids.^2,3 (±)7(8)-EpDPA and other epoxy metabolites of DHA modulate receptor and channel activities to evoke diverse effects, such as promoting vasodilation, inhibiting angiogenesis, and decreasing inflammatory and neuropathic pain.^3,4,5,6 (±)7(8)-EpDPA is a substrate of soluble epoxide hydrolase (KM = 15 µM), which converts it to the corresponding diol.³

This information has been provided by Cayman Chemical

References

1. Spector, A.A., and Kim, H.Y. Cytochrome P450 epoxygenase pathway of polyunsaturated fatty acid metabolism. Biochim. Biophys. Acta 1851(4), 356-365 (2015).

2. Fischer, R., Konkel, A., Mehling, H., et al. Dietary omega-3 fatty acids modulate the eicosanoid profile in man primarily via the CYP-epoxygenase pathway. J. Lipid Res. 55(6), 1150-1164 (2014).

3. 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).

4. 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).

5. Wang, R., Chai, Q., Lu, T., et al. Activation of vascular BK channels by docosahexaenoic acid is dependent on cytochrome P450 epoxygenase activity. Cardiovasc. Res. 90, 344-352 (2011).

6. Sato, K., Chino, D., Nishioka, N., et al. Pharmacological evidence showing significant roles for potassium channels and CYP epoxygenase metabolites in the relaxant effects of docosahexaenoic acid on the rat aorta contracted with U46619. Biol. Pharm. Bull. 37(3), 394-403 (2014).

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)

OHYKIJBTVXMLKX-MPQBXPHNSA-N

InChi (Click to copy)

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

SMILES (Click to copy)

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