2-(14,15-Epoxyeicosatrienoyl) Glycerol (BioDeep_00000033096)

   

human metabolite Endogenous


代谢物信息卡片


1,3-dihydroxypropan-2-yl (5Z,8Z,11Z)-13-(3-pentyloxiran-2-yl)trideca-5,8,11-trienoate

化学式: C23H38O5 (394.2719098)
中文名称:
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: CCCCCC1OC1C\C=C/C\C=C/C\C=C/CCCC(=O)OC(CO)CO
InChI: 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-

描述信息

2-(14,15-Epoxyeicosatrienoyl) glycerol, or 2-14,15-EG, is a cytochrome P450 metabolite of 2-arachidonoyl glycerol in the kidney (PMID: 17283047). 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 (PMID: 9285589, 9915812, 9650580). 2-AG is hydrolyzed by the enzyme monoacylglycerol lipase, terminating its biological activity, and metabolism by cyclooxygenase-2 and lipoxygenases has been documented (PMID: 12136125, 12052037). 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 (PMID: 17272674). 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 µM (PMID: 17283047). 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.
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]

同义名列表

15 个代谢物同义名

1,3-dihydroxypropan-2-yl (5Z,8Z,11Z)-13-(3-pentyloxiran-2-yl)trideca-5,8,11-trienoate; 14,15-Epoxy-(5Z,8Z,11Z)-eicosatrienoic acid 2-glyceryl ester; 14,15-Epoxy-(5Z,8Z,11Z)-icosatrienoic acid 2-glyceryl ester; 14,15-Epoxy-(5Z,8Z,11Z)-eicosatrienoate 2-glyceryl ester; 14,15-Epoxy-(5Z,8Z,11Z)-icosatrienoate 2-glyceryl ester; 2-Glyceryl-14,15-epoxy-(5Z,8Z,11Z)-eicosatrienoic acid; 2-Glyceryl 14,15-epoxy-(5Z,8Z,11Z)-icosatrienoic acid; 2-[14,15-Epoxy-(5Z,8Z,11Z)-eicosatrienoyl]glycerol; 2-Glyceryl-14,15-epoxy-(5Z,8Z,11Z)-eicosatrienoate; 2-[14,15-Epoxy-(5Z,8Z,11Z)-icosatrienoyl]glycerol; 2-(14,15-Epoxyeicosatrienoyl) Glycerol; 2-(14,15-epoxyeicosatrienoyl)glycerol; 14,15-EET 2-glyceryl ester; 2-Glyceryl 14,15-eet; 2-14,15-EG



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