Name: (±)17(18)-EpETE-Ethanolamide
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HIT ID:HIT218832879
Cas No:
Common Name:(±)17(18)-EpETE-Ethanolamide
alias:17,18-epoxy-Eicosatetraenoic Acid Ethanolamide, 17,18-EEQ-EA, (±)17,18-EEQ-Ethanolamide, (±)17(18)-EpETE-EA
alias:17,18-epoxy-Eicosatetraenoic Acid Ethanolamide, 17,18-EEQ-EA, (±)17,18-EEQ-Ethanolamide, (±)17(18)-EpETE-EA
IUPAC:16-(3-ethyloxiran-2-yl)-N-(2-hydroxyethyl)hexadeca-5,8,11,14-tetraenamide
IUPAC:16-(3-ethyloxiran-2-yl)-N-(2-hydroxyethyl)hexadeca-5,8,11,14-tetraenamide
InChI key:PVTVBNICUOQEDT-UHFFFAOYSA-N

Molecular Formula:C22H35NO3
Molecular Weight:361.526
Hydrogen Bond Donor (HBD):
Hydrogen Bond Acceptor (HBA):
LogP:
SMILES:CCC1OC1CC=CCC=CCC=CCC=CCCCC(=O)NCCO
SMILES:CCC1OC1CC=CCC=CCC=CCC=CCCCC(=O)NCCO

(±)17(18)-EpETE-Ethanolamide, an ω-3 endocannabinoid epoxide, originates from eicosapentaenoic ethanolamide (EPEA) through cytochrome P450 (CYP) epoxygenases action and is decomposed by soluble epoxide hydrolase (sEH) and fatty acid amide hydrolase (FA, AH). Its endogenous synthesis occurs in LPS-stimulated and EPEA-supplemented BV-2 microglia cells, a process inhibited by the CYP inhibitor ketoconazole. This compound mitigates IL-6 and nitrite levels while enhancing IL-10 production following LPS exposure in BV-2 microglia. At a dose of 50 µM, it prevents platelet aggregation caused by arachidonic acid but not that triggered by ADP, collagen, or ristocetin. Additionally, it facilitates the dilation of constricted bovine coronary arteries (ED50= 1.1 µM) and blocks VEGF-driven tubulogenesis in human microvascular endothelial cells (HMVECs).

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