1.0 2011-09-21 00:29:17 UTC 2015-07-21 06:57:41 UTC FDB023394 2-Arachidonylglycerol 2-Arachidonoylglycerol (2-AG) is a unique molecular species of monoacylglycerol isolated in 1995 from rat brain and canine gut as an endogenous ligand for the cannabinoid receptors. 2-AG is rapidly formed from arachidonic acid-containing phospholipids through increased phospholipid metabolism, such as enhanced inositol phospholipid turnover, in various tissues and cells upon stimulation. 2-AG binds to the cannabinoid receptors (CB1 and CB2) and exhibits a variety of cannabimimetic activities in vitro and in vivo. 2-Arachidonylglycerol is an endogenous cannabinoid (endocannabinoid). Endocannabinoids are a class of fatty acid derivatives defined by their ability to interact with the specific cannabinoid receptors that were originally identified as the targets of Delta9-tetrahydocannabinol (Delta9-THC), the psychoactive component of cannabis. Endocannabinoids have been implicated in a growing number of important physiological and behavioral events. Endocannabinoids are amides, esters and ethers of long chain polyunsaturated fatty acids, which act as new lipidic mediators. 2-AG is one of the main endogenous agonists of cannabinoid receptors, able to mimic several pharmacological effects of (-)-Delta9-tetrahydrocannabinol (THC), the active principle of Cannabis sativa preparations like hashish and marijuana. The activity of AEA and 2-AG at their receptors is limited by cellular uptake through an anandamide membrane transporter (AMT), followed by intracellular degradation. A fatty acid amide hydrolase (FAAH) is the main AEA hydrolase, whereas a monoacylglycerol lipase (MAGL) is critical in degrading 2-AG. (PMID: 16515464, 16278487, 16678907) MG(0:0/20:4(5Z,8Z,11Z,14Z)/0:0) is a monoacylglyceride. A monoglyceride, more correctly known as a monoacylglycerol, is a glyceride consisting of one fatty acid chain covalently bonded to a glycerol molecule through an ester linkage. Monoacylglycerol can be broadly divided into two groups; 1-monoacylglycerols (or 3-monoacylglycerols) and 2-monoacylglycerols, depending on the position of the ester bond on the glycerol moiety. Normally the 1-/3-isomers are not distinguished from each other and are termed 'alpha-monoacylglycerols', while the 2-isomers are beta-monoacylglycerols. Monoacylglycerols are formed biochemically via release of a fatty acid from diacylglycerol by diacylglycerol lipase or hormone sensitive lipase. Monoacylglycerols are broken down by monoacylglycerol lipase. They tend to be minor components only of most plant and animal tissues, and indeed would not be expected to accumulate because their strong detergent properties would have a disruptive effect on membranes. 2-Monoacylglycerols are a major end product of the intestinal digestion of dietary fats in animals via the enzyme pancreatic lipase. They are taken up directly by the intestinal cells and converted to triacylglycerols via the monoacylglycerol pathway before being transported in lymph to the liver. Mono- and Diglycerides are commonly added to commercial food products in small quantities. They act as emulsifiers, helping to mix ingredients such as oil and water that would not otherwise blend well. [HMDB] (5Z,8Z,11Z,14Z)-2-hydroxy-1-(hydroxymethyl)ethyl ester 5,8,11,14-Eicosatetraenoate (5Z,8Z,11Z,14Z)-2-hydroxy-1-(hydroxymethyl)ethyl ester 5,8,11,14-Eicosatetraenoic acid (all-Z)-2-hydroxy-1-(hydroxymethyl)ethyl ester 5,8,11,14-Eicosatetraenoate (all-Z)-2-hydroxy-1-(hydroxymethyl)ethyl ester 5,8,11,14-Eicosatetraenoic acid 2-(5Z,8Z,11Z,14Z-Eicosatetraenoyl)-glycerol 2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-rac-glycerol 2-AG 2-Ara-gl 2-arachidonoyl-glycerol 2-Arachidonoylglycerol 2-Arachidonyl glycerol 2-Monoarachidonoylglycerolbeta-monoacylglycerol MAG(0:0/20:4) MAG(0:0/20:4n6) MAG(0:0/20:4w6) MAG(20:4) MG(0:0/20:4(5Z,8Z,11Z,14Z)/0:0) MG(0:0/20:4) MG(0:0/20:4n6) MG(0:0/20:4w6) MG(20:4) C23H38O4 378.5454 378.277009704 1,3-dihydroxypropan-2-yl icosa-5,8,11,14-tetraenoate 1,3-dihydroxypropan-2-yl icosa-5,8,11,14-tetraenoate 53847-30-6 CCCCCC=CCC=CCC=CCC=CCCCC(=O)OC(CO)CO InChI=1S/C23H38O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-23(26)27-22(20-24)21-25/h6-7,9-10,12-13,15-16,22,24-25H,2-5,8,11,14,17-21H2,1H3 RCRCTBLIHCHWDZ-UHFFFAOYSA-N belongs to the class of organic compounds known as endocannabinoids. These are arachidonic acid derivatives containing either an N-acetylethanolamine(type 1) or a glycerol(types 2 and 3) moiety attached to the aliphatic tail. Endocannabinoids Organic compounds Lipids and lipid-like molecules Endocannabinoids Aliphatic acyclic compounds 2-monoacylglycerols Carbonyl compounds Carboxylic acid esters Fatty acid esters Hydrocarbon derivatives Monocarboxylic acids and derivatives Organic oxides Primary alcohols 2-acyl-sn-glycerol 2-arachidonoylglycerol-skeleton Alcohol Aliphatic acyclic compound Carbonyl group Carboxylic acid derivative Carboxylic acid ester Fatty acid ester Fatty acyl Glycerolipid Hydrocarbon derivative Monoacylglycerol Monocarboxylic acid or derivatives Monoradylglycerol Organic oxide Organic oxygen compound Organooxygen compound Primary alcohol a monoacylglycerol Solid logp 5.65 ALOGPS logs -5.44 ALOGPS solubility 1.37e-03 g/l ALOGPS logp 5.41 ChemAxon pka_strongest_acidic 14.28 ChemAxon pka_strongest_basic -3 ChemAxon iupac 1,3-dihydroxypropan-2-yl icosa-5,8,11,14-tetraenoate ChemAxon average_mass 378.5454 ChemAxon mono_mass 378.277009704 ChemAxon smiles CCCCCC=CCC=CCC=CCC=CCCCC(=O)OC(CO)CO ChemAxon formula C23H38O4 ChemAxon inchi InChI=1S/C23H38O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-23(26)27-22(20-24)21-25/h6-7,9-10,12-13,15-16,22,24-25H,2-5,8,11,14,17-21H2,1H3 ChemAxon inchikey RCRCTBLIHCHWDZ-UHFFFAOYSA-N ChemAxon polar_surface_area 66.76 ChemAxon refractivity 116.98 ChemAxon polarizability 44.82 ChemAxon rotatable_bond_count 18 ChemAxon acceptor_count 3 ChemAxon donor_count 2 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 108495 Specdb::CMs 121083 Specdb::CMs 813299 Specdb::CMs 813300 Specdb::CMs 813301 Specdb::CMs 813302 Specdb::MsMs 3398812 Specdb::MsMs 3398813 Specdb::MsMs 3398814 Specdb::MsMs 3398815 Specdb::MsMs 3398816 Specdb::MsMs 3398817 Specdb::MsMs 3398818 Specdb::MsMs 3398819 Specdb::MsMs 3398820 HMDB04666 #<Reference:0x000055ce324ac170> #<Reference:0x000055ce324abf68> #<Reference:0x000055ce324abdb0> 2-acylglycerol O-acyltransferase 1 Q96PD6 MOGAT1 2-acylglycerol O-acyltransferase 2 Q3SYC2 MOGAT2 2-acylglycerol O-acyltransferase 3 Q86VF5 MOGAT3 Ectonucleotide pyrophosphatase/phosphodiesterase family member 6 Q6UWR7 ENPP6 Lysophosphatidic acid phosphatase type 6 Q9NPH0 ACP6 Monoglyceride lipase Q99685 MGLL