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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2011-07-11 13:36:09 UTC
Update Date2020-02-26 21:39:01 UTC
HMDB IDHMDB0013657
Secondary Accession Numbers
  • HMDB13657
Metabolite Identification
Common Name2-Arachidonyl Glycerol ether
Description2-Arachidonyl glycerol ether (2-AG ether) has been isolated from porcine brain and its structure determined by mass spec analysis.1 2-AG ether has also been synthesized as an analog of the endogenous cannabinoid (CB), 2-AG, for structure activity testing.2 2-AG ether is a selective central cannabinoid (CB1) receptor agonist exhibiting Ki values of 21.2 nM and >3 µM at the CB1 and peripheral cannabinoid (CB2) receptors, respectively, and displays the typical tetrad of CB activities in mice.1 It is much more chemically stable than 2-AG, with an endogenous half-life of hours rather than minutes.3 However, it is at least 10-fold less potent than 2-AG in eliciting typical CB1-mediated responses.2 2-AG ether elicits modest reductions in IOP in rabbits when administered at doses exceeding 50 µg per eye.3 2-AG ether increases aqueous humor outflow via the CB1 receptor in the trabecular meshwork.
Structure
Data?1582753141
Synonyms
ValueSource
(5Z,8Z,11Z,14Z)-Icosatetraenyl-2-glyceryl etherChEBI
2-(5Z,8Z,11Z,14Z-Eicosatetraenyl)-sn-glycerolChEBI
2-AG etherChEBI
2-O-(5Z,8Z,11Z,14Z)-EicosatetraenylglycerolChEBI
5Z,8Z,11Z,14Z-Eicosatetraen-2-glyceryl etherChEBI
Noladin etherChEBI
2-ArachidonylglycerolHMDB
HU-310HMDB
NoladinHMDB
2-Arachidonyl glyceryl etherHMDB
Chemical FormulaC23H40O3
Average Molecular Weight364.5619
Monoisotopic Molecular Weight364.297745146
IUPAC Name2-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraen-1-yloxy]propane-1,3-diol
Traditional Name2-arachidonyl-glycerol
CAS Registry Number222723-55-9
SMILES
CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCCOC(CO)CO
InChI Identifier
InChI=1S/C23H40O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-26-23(21-24)22-25/h6-7,9-10,12-13,15-16,23-25H,2-5,8,11,14,17-22H2,1H3/b7-6-,10-9-,13-12-,16-15-
InChI KeyCUJUUWXZAQHCNC-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-arachidonylglyceryl-ether-skeleton
  • Monoalkylglycerol
  • Monoradylglycerol
  • Glycerolipid
  • Glycerol ether
  • Ether
  • Dialkyl ether
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

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 Solubility0.00038 g/LALOGPS
logP6.13ALOGPS
logP5.79ChemAxon
logS-6ALOGPS
pKa (Strongest Acidic)14.3ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area49.69 ŲChemAxon
Rotatable Bond Count18ChemAxon
Refractivity117.22 m³·mol⁻¹ChemAxon
Polarizability45.15 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00c0-9152000000-4f071d1ae17fba4da471Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-01b9-4290300000-e1b0c85cf9253f3d9540Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-4149000000-e4720c0dc226c8f75c6cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00fu-9552000000-acc6ac79c25f7b01fabcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0adi-9530000000-f3e8c4232a41b271712dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-4019000000-c1d518d9dd0e72949b1fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01ox-9014000000-d9fb7a4798c72d74ca06Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05fr-9010000000-a278d030fcbae6839865Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB029627
KNApSAcK IDNot Available
Chemspider ID4983515
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link2-Arachidonyl_glyceryl_ether
METLIN IDNot Available
PubChem Compound6483057
PDB IDNot Available
ChEBI ID75913
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.