8 (9) -EET

8 (9) -EET is one of the main metabolites produced by the metabolism of arachidonic acid (HY-109590) through the cytochrome P450 epoxide pathway. 8 (9) -EET is an effective substrate for COX-1 and COX-2. 8 (9) -EET activates PPARα in HEK293 cells and inhibits the activity of NF-κB induced by IL-1β in a PPARα-dependent and -independent manner. The (8S,9R) -isomer of 8 (9) -EET ([ (8S,9R) -EET]) causes vasoconstriction, thereby reducing renal plasma flow and glomerular filtration rate[1][2][3][4][5].

Product Specifications

CAS Number

[82864-43-5]

UNSPSC

12352005

Target

COX; Drug Metabolite; NF-κB; PPAR

Related Pathways

Cell Cycle/DNA Damage; Immunology/Inflammation; Metabolic Enzyme/Protease; NF-κB; Vitamin D Related/Nuclear Receptor

Applications

Metabolism-protein/nucleotide metabolism

Field of Research

Metabolic Disease

Smiles

CCCCC/C=C\C/C=C\C[C@H]1[C@H](O1)C/C=C\CCCC(O)=O

Molecular Formula

C20H32O3

Molecular Weight

320.47

References & Citations

[1]Chacos, N., Falck, J.R., Wixtrom, C., et al. Novel epoxides formed during the liver cytochrome P-450 oxidation of arachidonic acid. Biochem. Biophys. Res. Commun. 104 (3), 916-922 (1982) .|[2]Zhang, J.Y., Prakash, C., Yamashita, K., et al. Regiospecific and enantioselective metabolism of 8,9-epoxyeicosatrienoic acid by cyclooxygenase. Biochem. Biophys. Res. Commun. 183 (1), 138-143 (1992) .|[3]Bystrom, J., Wray, J.A., Sugden, M.C., et al. Endogenous epoxygenases are modulators of monocyte/macrophage activity. PloS One 6 (10), e26591 (2011) .|[4]Rand, A.A., Barnych, B., Morisseau, C., et al. Cyclooxygenase-derived proangiogenic metabolites of epoxyeicosatrienoic acids. Proc. Natl. Acad. Sci. USA 114 (17), 4370-4375 (2017) .|[5]Katoh T, et al. Glomerular stereospecific synthesis and hemodynamic actions of 8,9-epoxyeicosatrienoic acid in rat kidney. Am J Physiol. 1991 Oct;261 (4 Pt 2) :F578-86.