LIPID MAPS

Structure Database (LMSD)

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Common Name

8(9)-EpETE

Systematic Name

(+/-)-8(9)-epoxy-5Z,11Z,14Z,17Z-eicosatetraenoic acid

Synonyms

LM ID

LMFA03000001

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

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

Classification

Biological Context

Eicosapentaenoic acid (EPA) is converted to epoxyeicosatetraenoic acids (EpETEs) by several cytochrome P450 isoforms.¹ The major product of this epoxygenase pathway, (±)17(18)-EpETE, relaxes vascular and airway smooth muscle by activating large conductance Ca2+-activated K+ (BKCa) channels by directly interacting with BKα channel subunits.^2,3,4 (±)8(9)-EpETE is an epoxygenase pathway product produced from EPA by CYP450 both in vitro and in vivo.⁵ The biological actions and physiological effects of this epoxide remain to be determined.

This information has been provided by Cayman Chemical

References

1. Barbosa-Sicard, E., Markovic, M., Honeck, H., et al. Eicosapentaenoic acid metabolism by cytochrome P450 enzymes of the CYP2C subfamily. Biochem. Biophys. Res. Commun. 329, 1275-1281 (2005).

2. Lauterbach, B., Barbosa-Sicard, E., Wang, M.H., et al. Cytochrome P450-dependent eicosapentaenoic acid metabolites are novel BK channel activators. Hypertension 39(2 Pt. 2), 609-613 (2002).

3. Hercule, H.C., Salanova, B., Essin, K., et al. The vasodilator 17,18-epoxyeicosatetraenoic acid targets the pore-forming BKα channel subunit in rodents. Exp. Physiol. 92(6), 1067-1076 (2007).

4. Morin, C., Sirois, M., Echave, V., et al. Relaxing effects of 17(18)-EpETE on arterial and airway smooth muscles in human lung. Am. J. Physiol. Lung Cell. Mol. Physiol. 296, L130-L139 (2009).

5. Arnold, C., Markovic, M., Blossey, K., et al. Arachidonic acid-metabolizing cytochrome P450 enzymes are targets of omega-3 fatty acids. The Journal of Biological Chemisty 285(43), 32720-32733 (2010).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Rattus norvegicus (#10116)

Mammalia (#40674)

Cytochrome P450 and arachidonic acid bioactivation. Molecular and functional properties of the arachidonate monooxygenase.,
J Lipid Res, 2000

Pubmed ID: 10681399

String Representations

InChiKey (Click to copy)

YKIOHMXLFWMWKD-JJUYGIQRSA-N

InChi (Click to copy)

InChI=1S/C20H30O3/c1-2-3-4-5-6-7-8-9-12-15-18-19(23-18)16-13-10-11-14-17-20(21)22/h3-4,6-7,9-10,12-13,18-19H,2,5,8,11,14-17H2,1H3,(H,21,22)/b4-3-,7-6-,12-9-,13-10-

SMILES (Click to copy)

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