2-(14,15-Epoxyeicosatrienoyl) glycerol
IUPAC 名称
1,3-dihydroxypropan-2-yl (5Z,8Z,11Z)-13-(3-pentyloxiran-2-yl)trideca-5,8,11-trienoate
描述
2-Arachidonoyl glycerol (2-AG) is an endogenous central cannabinoid (CB1) receptor agonist that is present at relatively high levels in the central nervous system.1,2,3 2-AG is hydrolyzed by the enzyme monoacylglycerol lipase, terminating its biological activity, and metabolism by cyclooxygenase-2 and lipoxygenases has been documented.4,5 The related endocannabinoid, 2-arachidonoyl ethanolamide (AEA), can be metabolized by cytochrome P450 (CYP450) enzymes in human liver and kidney to a number of epoxy-ethanolamide derivatives.6 2-14,15-EG is a novel CYP450 metabolite of 2-AG in the kidney.7 2-14,15-EG is a potent mitogen for renal epithelial cells, increasing DNA synthesis in LLCPKcl4 cells at concentrations as low as 100 nM and doubling cell proliferation rates at 1 ?M.7 In these cells, 2-14,15-EG activates the metalloprotease ADAM17, which cleaves proTGF-α and releases TGF-α as a ligand that initiates the EGFR-ERK signalling pathway. [HMDB]
异构
CCCCCC1OC1C\C=C/C\C=C/C\C=C/CCCC(=O)OC(CO)CO
InChI标识符
InChI=1S/C23H38O5/c1-2-3-12-15-21-22(28-21)16-13-10-8-6-4-5-7-9-11-14-17-23(26)27-20(18-24)19-25/h4,6-7,9-10,13,20-22,24-25H,2-3,5,8,11-12,14-19H2,1H3/b6-4-,9-7-,13-10-
键
LPMVKZXODWQHGJ-ILYOTBPNSA-N