Common Name2-(5z,8z,11z,14z-eicosatetraenoyl)-glycerol
DescriptionMG(0:0/20:4(5Z,8Z,11Z,14Z)/0:0), also known as 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-AG 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-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 ).
Structure
Molecular FormulaC23H38O4
Average Mass378.54540
Monoisotopic Mass378.27701
IUPAC Name1,3-dihydroxypropan-2-yl (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoate
Traditional Name2-arachidonoylglycerol
CAS Registry Number53847-30-6
SMILESCCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)OC(CO)CO
InChI IdentifierInChI=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/b7-6-,10-9-,13-12-,16-15-
InChI KeyRCRCTBLIHCHWDZ-DOFZRALJSA-N
CHEBI IDCHEBI:52392
HMDB IDHMDB0004666
StateNot Available
Water Solubility1.37e-03 g/l
logP5.65
logS-5.44
pKa (Strongest Acidic)14.28
pKa (Strongest Basic)-2.98
Hydrogen Acceptor Count3
Hydrogen Donor Count2
Polar Surface Area66.76 Ų
Rotatable Bond Count18
Physiological Charge0
Formal Charge0
Refractivity116.98 m³·mol⁻¹
Polarizability44.96

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