1.0 2011-09-21 01:58:35 UTC 2015-07-21 06:59:46 UTC FDB029621 2-(14,15-Epoxyeicosatrienoyl) glycerol 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-&#945; and releases TGF-&#945; as a ligand that initiates the EGFR-ERK signalling pathway. [HMDB] 2-14,15-EG C23H38O5 394.5448 394.271924326 1,3-dihydroxypropan-2-yl (5Z,8Z,11Z)-13-(3-pentyloxiran-2-yl)trideca-5,8,11-trienoate 1,3-dihydroxypropan-2-yl (5Z,8Z,11Z)-13-(3-pentyloxiran-2-yl)trideca-5,8,11-trienoate 848667-56-1 CCCCCC1OC1C\C=C/C\C=C/C\C=C/CCCC(=O)OC(CO)CO 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- LPMVKZXODWQHGJ-ILYOTBPNSA-N belongs to the class of organic compounds known as 2-monoacylglycerols. These are monoacylglycerols containing a glycerol acylated at the 2-position. 2-monoacylglycerols Organic compounds Lipids and lipid-like molecules Glycerolipids Monoradylglycerols Aliphatic heteromonocyclic compounds Carbonyl compounds Carboxylic acid esters Dialkyl ethers Epoxides Fatty acid esters Hydrocarbon derivatives Monocarboxylic acids and derivatives Organic oxides Oxacyclic compounds Primary alcohols 2-acyl-sn-glycerol Alcohol Aliphatic heteromonocyclic compound Carbonyl group Carboxylic acid derivative Carboxylic acid ester Dialkyl ether Ether Fatty acid ester Fatty acyl Hydrocarbon derivative Monocarboxylic acid or derivatives Organic oxide Organic oxygen compound Organoheterocyclic compound Organooxygen compound Oxacycle Oxirane Primary alcohol Solid logp 4.88 ALOGPS logs -4.99 ALOGPS solubility 4.08e-03 g/l ALOGPS logp 4.47 ChemAxon pka_strongest_acidic 14.28 ChemAxon pka_strongest_basic -3 ChemAxon iupac 1,3-dihydroxypropan-2-yl (5Z,8Z,11Z)-13-(3-pentyloxiran-2-yl)trideca-5,8,11-trienoate ChemAxon average_mass 394.5448 ChemAxon mono_mass 394.271924326 ChemAxon smiles CCCCCC1OC1C\C=C/C\C=C/C\C=C/CCCC(=O)OC(CO)CO ChemAxon formula C23H38O5 ChemAxon 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- ChemAxon inchikey LPMVKZXODWQHGJ-ILYOTBPNSA-N ChemAxon polar_surface_area 79.29 ChemAxon refractivity 115.38 ChemAxon polarizability 46.63 ChemAxon rotatable_bond_count 18 ChemAxon acceptor_count 4 ChemAxon donor_count 2 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 18767 Specdb::CMs 40152 Specdb::CMs 117044 Specdb::CMs 161946 Specdb::CMs 1011107 Specdb::CMs 1011108 Specdb::CMs 1011109 Specdb::MsMs 307678 Specdb::MsMs 307679 Specdb::MsMs 307680 Specdb::MsMs 351685 Specdb::MsMs 351686 Specdb::MsMs 351687 Specdb::MsMs 2313251 Specdb::MsMs 2313252 Specdb::MsMs 2313253 Specdb::MsMs 2651951 Specdb::MsMs 2651952 Specdb::MsMs 2651953 Specdb::MsMs 2673919 Specdb::MsMs 2673920 Specdb::MsMs 2673921 Specdb::MsMs 2974494 Specdb::MsMs 2974495 Specdb::MsMs 2974496 HMDB13651 #<Reference:0x000055ce3205dce0> #<Reference:0x000055ce3205db28> #<Reference:0x000055ce3205d970> #<Reference:0x000055ce3205d7b8> #<Reference:0x000055ce3205d600> #<Reference:0x000055ce3205d448> #<Reference:0x000055ce3205d290>