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Record Information
Version3.6
Creation Date2006-08-13 23:27:52 UTC
Update Date2016-02-11 01:06:45 UTC
HMDB IDHMDB04666
Secondary Accession Numbers
  • HMDB11548
Metabolite Identification
Common Name2-Arachidonylglycerol
Description2-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 ). 2-Arachidonoylglycerol, or 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.
Structure
Thumb
Synonyms
ValueSource
2-(5Z,8Z,11Z,14Z-Eicosatetraenoyl)-glycerolChEBI
2-AGChEBI
2-Ara-GLChEBI
2-Arachidonoyl-glycerolChEBI
2-Arachidonyl-glycerolChEBI
1,3-Dihydroxypropan-2-yl (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoic acidGenerator
(5Z,8Z,11Z,14Z)-2-Hydroxy-1-(hydroxymethyl)ethyl ester 5,8,11,14-eicosatetraenoateHMDB
(5Z,8Z,11Z,14Z)-2-Hydroxy-1-(hydroxymethyl)ethyl ester 5,8,11,14-eicosatetraenoic acidHMDB
(all-Z)-2-Hydroxy-1-(hydroxymethyl)ethyl ester 5,8,11,14-eicosatetraenoateHMDB
(all-Z)-2-Hydroxy-1-(hydroxymethyl)ethyl ester 5,8,11,14-eicosatetraenoic acidHMDB
1-MonoacylglycerideHMDB
1-MonoacylglycerolHMDB
2-(5Z,8Z,11Z,14Z-Eicosatetraenoyl)-rac-glycerolHMDB
2-Arachidonyl glycerolHMDB
2-Monoarachidonoylglycerolbeta-monoacylglycerolHMDB
b-MonoacylglycerolHMDB
beta-MonoacylglycerolHMDB
MAG(0:0/20:4)HMDB
MAG(0:0/20:4n6)HMDB
MAG(0:0/20:4W6)HMDB
MAG(20:4)HMDB
MG(0:0/20:4(5Z,8Z,11Z,14Z)/0:0)HMDB
MG(0:0/20:4)HMDB
MG(0:0/20:4n6)HMDB
MG(0:0/20:4W6)HMDB
MG(20:4)HMDB
Chemical FormulaC23H38O4
Average Molecular Weight378.5454
Monoisotopic Molecular Weight378.277009704
IUPAC Name1,3-dihydroxypropan-2-yl (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoate
Traditional Name2-arachidonoylglycerol
CAS Registry Number53847-30-6
SMILES
CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(=O)OC(CO)CO
InChI Identifier
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/b7-6-,10-9-,13-12-,16-15-
InChI KeyInChIKey=RCRCTBLIHCHWDZ-DOFZRALJSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as 2-monoacylglycerols. These are monoacylglycerols containing a glycerol acylated at the 2-position.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerolipids
Sub ClassMonoradylglycerols
Direct Parent2-monoacylglycerols
Alternative Parents
Substituents
  • 2-acyl-sn-glycerol
  • Fatty acid ester
  • Fatty acyl
  • Saccharide
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • 2-arachidonoylglycerol-skeleton
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Energy source
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane component
  • Membrane integrity/stability
Application
  • Emuslifiers
  • Food additives
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0014 mg/mLALOGPS
logP5.65ALOGPS
logP5.41ChemAxon
logS-5.4ALOGPS
pKa (Strongest Acidic)14.28ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.76 Å2ChemAxon
Rotatable Bond Count18ChemAxon
Refractivity116.98 m3·mol-1ChemAxon
Polarizability44.96 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
Tissue Location
  • All Tissues
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified7.8 +/- 4.6 uMAdult (>18 years old)Both
Normal
details
Cerebrospinal Fluid (CSF)Detected and Quantified0.01848 +/- 0.00617 uMNot SpecifiedNot SpecifiedNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.01062 +/- 0.00458 uMNot SpecifiedNot SpecifiedNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.1596 +/- 0.1102 uMNot SpecifiedBothNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
Cerebrospinal Fluid (CSF)Detected and Quantified0.2095 +/- 0.14656 uMAdult (>18 years old)Bothepilepsy details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023394
KNApSAcK IDNot Available
Chemspider ID4445451
KEGG Compound IDC13856
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB04666
Metagene LinkHMDB04666
METLIN IDNot Available
PubChem Compound5282280
PDB IDNot Available
ChEBI ID52392
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Bari M, Battista N, Fezza F, Gasperi V, Maccarrone M: New insights into endocannabinoid degradation and its therapeutic potential. Mini Rev Med Chem. 2006 Mar;6(3):257-68. [16515464 ]
  2. Alger BE: Endocannabinoid identification in the brain: studies of breakdown lead to breakthrough, and there may be NO hope. Sci STKE. 2005 Nov 8;2005(309):pe51. [16278487 ]
  3. Sugiura T, Kishimoto S, Oka S, Gokoh M: Biochemistry, pharmacology and physiology of 2-arachidonoylglycerol, an endogenous cannabinoid receptor ligand. Prog Lipid Res. 2006 Sep;45(5):405-46. Epub 2006 Apr 19. [16678907 ]

Enzymes

General function:
Lipid transport and metabolism
Specific function:
Converts monoacylglycerides to free fatty acids and glycerol. Hydrolyzes the endocannabinoid 2-arachidonoylglycerol, and thereby contributes to the regulation of endocannabinoid signaling, nociperception and perception of pain (By similarity). Regulates the levels of fatty acids that serve as signaling molecules and promote cancer cell migration, invasion and tumor growth.
Gene Name:
MGLL
Uniprot ID:
Q99685
Molecular weight:
Not Available
General function:
Involved in hydrolase activity
Specific function:
In adipose tissue and heart, it primarily hydrolyzes stored triglycerides to free fatty acids, while in steroidogenic tissues, it principally converts cholesteryl esters to free cholesterol for steroid hormone production.
Gene Name:
LIPE
Uniprot ID:
Q05469
Molecular weight:
116596.715
General function:
Involved in transferase activity, transferring acyl groups other than amino-acyl groups
Specific function:
Catalyzes the formation of diacylglycerol from 2-monoacylglycerol and fatty acyl-CoA. Has a preference toward monoacylglycerols containing unsaturated fatty acids in an order of C18:3 > C18:2 > C18:1 > C18:0. Plays a central role in absorption of dietary fat in the small intestine by catalyzing the resynthesis of triacylglycerol in enterocytes. May play a role in diet-induced obesity.
Gene Name:
MOGAT2
Uniprot ID:
Q3SYC2
Molecular weight:
38195.285
General function:
Involved in transferase activity, transferring acyl groups other than amino-acyl groups
Specific function:
Catalyzes the formation of diacylglycerol from 2-monoacylglycerol and fatty acyl-CoA. Probably not involved in absorption of dietary fat in the small intestine (By similarity).
Gene Name:
MOGAT1
Uniprot ID:
Q96PD6
Molecular weight:
38812.19
General function:
Involved in transferase activity, transferring acyl groups other than amino-acyl groups
Specific function:
Catalyzes the formation of diacylglycerol from 2-monoacylglycerol and fatty acyl-CoA. Also able to catalyze the terminal step in triacylglycerol synthesis by using diacylglycerol and fatty acyl-CoA as substrates. Has a preference toward palmitoyl-CoA and oleoyl-CoA. May be involved in absorption of dietary fat in the small intestine by catalyzing the resynthesis of triacylglycerol in enterocytes.
Gene Name:
MOGAT3
Uniprot ID:
Q86VF5
Molecular weight:
38729.84
General function:
Involved in acid phosphatase activity
Specific function:
Hydrolyzes lysophosphatidic acid to monoacylglycerol.
Gene Name:
ACP6
Uniprot ID:
Q9NPH0
Molecular weight:
48853.955
General function:
Involved in NAD+ kinase activity
Specific function:
Lipid kinase that can phosphorylate both monoacylglycerol and diacylglycerol to form lysophosphatidic acid (LPA) and phosphatidic acid (PA), respectively. Does not phosphorylate sphingosine. Overexpression increases the formation and secretion of LPA, resulting in transactivation of EGFR and activation of the downstream MAPK signaling pathway, leading to increased cell growth
Gene Name:
AGK
Uniprot ID:
Q53H12
Molecular weight:
47136.8
General function:
Involved in catalytic activity
Specific function:
Choline-specific glycerophosphodiester phosphodiesterase. The preferred substrate may be lysosphingomyelin (By similarity). Hydrolyzes lysophosphatidylcholine (LPC) to form monoacylglycerol and phosphorylcholine but not lysophosphatidic acid, showing it has a lysophospholipase C activity. Has a preference for LPC with short (12:0 and 14:0) or polyunsaturated (18:2 and 20:4) fatty acids. Also hydrolyzes glycerophosphorylcholine and sphingosylphosphorylcholine efficiently. Hydrolyzes the classical substrate for phospholipase C, p-nitrophenyl phosphorylcholine in vitro, while it does not hydrolyze the classical nucleotide phosphodiesterase substrate, p-nitrophenyl thymidine 5'-monophosphate. Does not hydrolyze diacyl phospholipids such as phosphatidylethanolamine, phosphatidylinositol, phosphatidylserine, phosphatidylglycerol and phosphatidic acid.
Gene Name:
ENPP6
Uniprot ID:
Q6UWR7
Molecular weight:
50240.625