Showing metabocard for 2-Arachidonylglycerol (BMDB0004666)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 23:10:03 UTC
Update Date2020-05-11 20:40:55 UTC
BMDB IDBMDB0004666
Secondary Accession Numbers
  • BMDB04666
Metabolite Identification
Common Name2-Arachidonylglycerol
DescriptionMG(0:0/20:4(5Z,8Z,11Z,14Z)/0:0) belongs to the family of monoradyglycerols, which are glycerolipids lipids containing a common glycerol backbone to which at one fatty acyl group is attached. Their general formula is [R1]OCC(CO[R2])O[R3]. MG(0:0/20:4(5Z,8Z,11Z,14Z)/0:0) is made up of one 5Z,8Z,11Z,14Z-eicosatetraenoyl(R2).
Structure
Thumb
MOLSDFPDBSMILESInChI
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
StatusExpected but not Quantified
OriginNot Available
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • 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
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0l0i-5290110000-f742efe3985e3840860aView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0009000000-3193f1e5874b95385d69View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004k-0009000000-627d06b5ba2360a06067View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00i2-0009000000-0762851e03f624970475View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0009000000-5e905142605905a46679View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a90-0009000000-ae7594dce5d303ff168aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0bti-0039000000-746b8a740d001af85c5aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0000900000-e64013c0e57ed934df45View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0000900000-e64013c0e57ed934df45View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fbf-0009300000-62825ca83031f6d152ecView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0009000000-c6ed117899d7fd7906f3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004j-0009000000-d5b85743041436ea2e66View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00i0-0009000000-7556d5d8a8a555162413View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00fu-8029000000-9c1a42f92892713859abView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0kmu-9023000000-df51ee22c1d10b8fbdc2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4r-9232000000-e481aacc04dad6bfc856View in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Membrane
Biospecimen Locations
  • All Tissues
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
All TissuesExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
PlacentaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0004666
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
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available