Name: (±)5(6)-EET
Rating: 5 (10 reviews)

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HIT ID:HIT214320956
Cas No:87173-80-6;98103-47-0
常用名:(±)5(6)-EET
IUPAC:4-[(2S,3R)-3-[(2Z,5Z,8Z)-tetradeca-2,5,8-trien-1-yl]oxiran-2-yl]butanoic acid
IUPAC:4-[(2S,3R)-3-[(2Z,5Z,8Z)-tetradeca-2,5,8-trien-1-yl]oxiran-2-yl]butanoic acid
InChI key:VBQNSZQZRAGRIX-GSKBNKFLSA-N

分子式:C20H32O3
分子量:320.473
氢键供体数 (HBD):
氢键受体数 (HBA):
LogP:
SMILES:CCCCC\C=C/C\C=C/C\C=C/C[C@H]1O[C@H]1CCCC(O)=O
SMILES:CCCCC\C=C/C\C=C/C\C=C/C[C@H]1O[C@H]1CCCC(O)=O

5(6)-EET is a fully racemic version of the enantiomeric forms biosynthesized from arachidonic acid by cytochrome P450 enzymes. In solution, 5(6)-EET degrades into 5,6-DiHET and 5(6)-δ-lactone, which can be converted to 5(6)-DiHET and quantified by GC-MS. In neuroendocrine cells, such as the anterior pituitary and pancreatic islets, 5(6)-EET has been implicated in the mobilization of calcium and hormone secretion. 5(6)-EET is an inhibitor of T-type voltage-gated calcium channels (Cav3) that inhibits isoforms Cav3.1, Cav3.2 (IC50 = 0.54 μM), and Cav3.3 and decreases nifedipine-resistant phenylephrine-induced vasoconstriction in isolated mouse mesenteric arteries via Cav3.2 blockade when used at a concentration of 3 μM. In addition, it is a substrate of COX-1 and COX-2, as measured by oxygen consumption and product formation assays when used at a concentration of 50 μM. (±)5(6)-EET is provided as a mixture of the free acid and lactone.

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