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Showing Compound 2-Arachidonyl glycerol ether (FDB029627)

Record Information
Version1.0
Creation date2011-09-21 01:58:42 UTC
Update date2015-07-21 06:59:47 UTC
Primary IDFDB029627
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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 ?M 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 ?g per eye.3 2-AG ether increases aqueous humor outflow via the CB1 receptor in the trabecular meshwork. [HMDB]
CAS Number222723-55-9
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
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
Chemical FormulaC23H40O3
IUPAC name2-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraen-1-yloxy]propane-1,3-diol
InChI IdentifierInChI=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
Isomeric SMILESCCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCCOC(CO)CO
Average Molecular Weight364.5619
Monoisotopic Molecular Weight364.297745146
Classification
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:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS2-Arachidonyl glycerol ether, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00c0-9152000000-4f071d1ae17fba4da471Spectrum
Predicted GC-MS2-Arachidonyl glycerol ether, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-01b9-4290300000-e1b0c85cf9253f3d9540Spectrum
Predicted GC-MS2-Arachidonyl glycerol ether, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-4149000000-e4720c0dc226c8f75c6c2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00fu-9552000000-acc6ac79c25f7b01fabc2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0adi-9530000000-f3e8c4232a41b271712d2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-4019000000-c1d518d9dd0e72949b1f2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01ox-9014000000-d9fb7a4798c72d74ca062017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05fr-9010000000-a278d030fcbae68398652017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0abc-9001000000-cd0050820da64ef90ba72021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9010000000-7045d2ee77595c5503b92021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9020000000-84b3341a3a8edfdd26ca2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0100-9475000000-1098e6232c1c00d8484d2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9421000000-67ab03b66d2ae09203752021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-067m-9200000000-d2ec4200655bc27e732f2021-09-24View Spectrum
NMRNot Available
ChemSpider ID4983515
ChEMBL IDCHEMBL146346
KEGG Compound IDNot Available
Pubchem Compound ID6483057
Pubchem Substance IDNot Available
ChEBI ID345740
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB13657
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
Processing...
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference