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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-08-13 23:27:52 UTC
Update Date2022-03-07 02:49:21 UTC
HMDB IDHMDB0004666
Secondary Accession Numbers
  • HMDB0011548
  • HMDB04666
  • HMDB11548
Metabolite Identification
Common NameMG(0:0/20:4(5Z,8Z,11Z,14Z)/0:0)
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
Data?1582752310
Synonyms
ValueSource
2-(5Z,8Z,11Z,14Z-Eicosatetraenoyl)-glycerolChEBI
2-AGChEBI
2-Ara-GLChEBI
2-Arachidonoyl-glycerolChEBI
2-Arachidonyl-glycerolChEBI
2-Arachidonoyl-sn-glycerolKegg
(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(20:4)HMDB
MG(20:4)HMDB
2-ArachidonoylglycerolHMDB
Glyceryl 2-arachidonateHMDB
2-MonoarachidonoylglycerolHMDB
2-ArachidonylglycerolHMDB
MAG(0:0/20:4(5Z,8Z,11Z,14Z)/0:0)HMDB
MAG(0:0/20:4n6/0:0)HMDB
MAG(0:0/20:4W6/0:0)HMDB
MAG(20:4(5Z,8Z,11Z,14Z))HMDB
MAG(20:4n6)HMDB
MAG(20:4W6)HMDB
MG(0:0/20:4n6/0:0)HMDB
MG(0:0/20:4W6/0:0)HMDB
MG(20:4(5Z,8Z,11Z,14Z))HMDB
MG(20:4n6)HMDB
MG(20:4W6)HMDB
MG(0:0/20:4(5Z,8Z,11Z,14Z)/0:0)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
[H]C(CO)(CO)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC
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 KeyRCRCTBLIHCHWDZ-DOFZRALJSA-N
Chemical Taxonomy
Description 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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassEndocannabinoids
Sub ClassNot Available
Direct ParentEndocannabinoids
Alternative Parents
Substituents
  • 2-arachidonoylglycerol-skeleton
  • 2-acyl-sn-glycerol
  • Monoradylglycerol
  • Monoacylglycerol
  • Glycerolipid
  • Fatty acid ester
  • Fatty acyl
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Primary alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Organooxygen compound
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0014 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count18ChemAxon
Refractivity116.98 m³·mol⁻¹ChemAxon
Polarizability44.96 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+204.10931661259
DarkChem[M-H]-203.27131661259
DeepCCS[M+H]+198.16630932474
DeepCCS[M-H]-195.80830932474
DeepCCS[M-2H]-229.86930932474
DeepCCS[M+Na]+205.18330932474
AllCCS[M+H]+201.732859911
AllCCS[M+H-H2O]+199.332859911
AllCCS[M+NH4]+204.032859911
AllCCS[M+Na]+204.632859911
AllCCS[M-H]-197.532859911
AllCCS[M+Na-2H]-200.032859911
AllCCS[M+HCOO]-202.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
MG(0:0/20:4(5Z,8Z,11Z,14Z)/0:0)[H]C(CO)(CO)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC3169.9Standard polar33892256
MG(0:0/20:4(5Z,8Z,11Z,14Z)/0:0)[H]C(CO)(CO)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC2539.8Standard non polar33892256
MG(0:0/20:4(5Z,8Z,11Z,14Z)/0:0)[H]C(CO)(CO)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC2880.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
MG(0:0/20:4(5Z,8Z,11Z,14Z)/0:0),1TMS,isomer #1CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)OC(CO)CO[Si](C)(C)C2902.4Semi standard non polar33892256
MG(0:0/20:4(5Z,8Z,11Z,14Z)/0:0),2TMS,isomer #1CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)OC(CO[Si](C)(C)C)CO[Si](C)(C)C2941.4Semi standard non polar33892256
MG(0:0/20:4(5Z,8Z,11Z,14Z)/0:0),1TBDMS,isomer #1CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)OC(CO)CO[Si](C)(C)C(C)(C)C3136.5Semi standard non polar33892256
MG(0:0/20:4(5Z,8Z,11Z,14Z)/0:0),2TBDMS,isomer #1CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)OC(CO[Si](C)(C)C(C)(C)C)CO[Si](C)(C)C(C)(C)C3416.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - MG(0:0/20:4(5Z,8Z,11Z,14Z)/0:0) GC-MS (2 TMS) - 70eV, Positivesplash10-0l0i-5290110000-f742efe3985e3840860a2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - MG(0:0/20:4(5Z,8Z,11Z,14Z)/0:0) GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - MG(0:0/20:4(5Z,8Z,11Z,14Z)/0:0) 10V, Positive-QTOFsplash10-0002-0009000000-3193f1e5874b95385d692017-10-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - MG(0:0/20:4(5Z,8Z,11Z,14Z)/0:0) 20V, Positive-QTOFsplash10-004k-0009000000-627d06b5ba2360a060672017-10-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - MG(0:0/20:4(5Z,8Z,11Z,14Z)/0:0) 40V, Positive-QTOFsplash10-00i2-0009000000-0762851e03f6249704752017-10-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - MG(0:0/20:4(5Z,8Z,11Z,14Z)/0:0) 10V, Positive-QTOFsplash10-004i-0009000000-5e905142605905a466792021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - MG(0:0/20:4(5Z,8Z,11Z,14Z)/0:0) 20V, Positive-QTOFsplash10-0a90-0009000000-ae7594dce5d303ff168a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - MG(0:0/20:4(5Z,8Z,11Z,14Z)/0:0) 40V, Positive-QTOFsplash10-0bti-0039000000-746b8a740d001af85c5a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - MG(0:0/20:4(5Z,8Z,11Z,14Z)/0:0) 10V, Positive-QTOFsplash10-0udi-0000900000-e64013c0e57ed934df452021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - MG(0:0/20:4(5Z,8Z,11Z,14Z)/0:0) 20V, Positive-QTOFsplash10-0udi-0000900000-e64013c0e57ed934df452021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - MG(0:0/20:4(5Z,8Z,11Z,14Z)/0:0) 40V, Positive-QTOFsplash10-0fbf-0009300000-62825ca83031f6d152ec2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - MG(0:0/20:4(5Z,8Z,11Z,14Z)/0:0) 10V, Positive-QTOFsplash10-0002-0009000000-c6ed117899d7fd7906f32021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - MG(0:0/20:4(5Z,8Z,11Z,14Z)/0:0) 20V, Positive-QTOFsplash10-004j-0009000000-d5b85743041436ea2e662021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - MG(0:0/20:4(5Z,8Z,11Z,14Z)/0:0) 40V, Positive-QTOFsplash10-00i0-0009000000-7556d5d8a8a5551624132021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - MG(0:0/20:4(5Z,8Z,11Z,14Z)/0:0) 10V, Negative-QTOFsplash10-00fu-8029000000-9c1a42f92892713859ab2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - MG(0:0/20:4(5Z,8Z,11Z,14Z)/0:0) 20V, Negative-QTOFsplash10-0kmu-9023000000-df51ee22c1d10b8fbdc22021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - MG(0:0/20:4(5Z,8Z,11Z,14Z)/0:0) 40V, Negative-QTOFsplash10-0a4r-9232000000-e481aacc04dad6bfc8562021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Urine
Tissue Locations
  • All Tissues
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
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
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Cerebrospinal Fluid (CSF)Detected and Quantified0.2095 +/- 0.14656 uMAdult (>18 years old)Bothepilepsy details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
Associated Disorders and Diseases
Disease References
Epilepsy
  1. Romigi A, Bari M, Placidi F, Marciani MG, Malaponti M, Torelli F, Izzi F, Prosperetti C, Zannino S, Corte F, Chiaramonte C, Maccarrone M: Cerebrospinal fluid levels of the endocannabinoid anandamide are reduced in patients with untreated newly diagnosed temporal lobe epilepsy. Epilepsia. 2010 May;51(5):768-72. doi: 10.1111/j.1528-1167.2009.02334.x. Epub 2009 Oct 8. [PubMed:19817812 ]
Colorectal cancer
  1. Wang X, Wang J, Rao B, Deng L: Gut flora profiling and fecal metabolite composition of colorectal cancer patients and healthy individuals. Exp Ther Med. 2017 Jun;13(6):2848-2854. doi: 10.3892/etm.2017.4367. Epub 2017 Apr 20. [PubMed:28587349 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023394
KNApSAcK IDNot Available
Chemspider ID4445451
KEGG Compound IDC13856
BioCyc IDCPD-12600
BiGG IDNot Available
Wikipedia Link2-Arachidonoylglycerol
METLIN IDNot Available
PubChem Compound5282280
PDB IDNot Available
ChEBI ID52392
Food Biomarker OntologyNot Available
VMH IDC13856
MarkerDB IDNot Available
Good Scents IDNot Available
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. [PubMed: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. [PubMed: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. [PubMed:16678907 ]
  4. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

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