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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2011-07-11 10:54:15 UTC
Update Date2022-03-07 02:51:34 UTC
HMDB IDHMDB0013655
Secondary Accession Numbers
  • HMDB13655
Metabolite Identification
Common NameO-Arachidonoyl Ethanolamine
DescriptionArachidonoyl ethanolamide (AEA) was the first endogenous cannabinoid to be isolated and characterized as an agonist acting on the same receptors (CB1 and CB2) as tetrahydrocannabinols (THC). Since that time, a number of related endocannabinoids have been isolated, most notably 2-arachidonoyl glycerol (2-AG).O-Arachidonoyl ethanolamine hydrochloride (O-AEA) is a recently isolated constituent of human and rat brain wherein the ethanolamine moiety is attached "backwards", as an ester instead of an amide, as in AEA.1,2,4 O-AEA has mixed agonist/antagonist activity at the CB1 receptor and does not appear to be the native endogenous cannabinoid agonist at this receptor. This is in keeping with other observations that 2-AG is the primary endogenous CB1 receptor ligand.
Structure
Data?1582753140
Synonyms
ValueSource
Arachidonic acid-(2-aminoethyl)-esterHMDB
O-AEAHMDB
VirodhamineHMDB
O-Arachidonyl ethanol amineMeSH, HMDB
O-Arachidonoyl ethanolamineMeSH
Chemical FormulaC22H37NO2
Average Molecular Weight347.5347
Monoisotopic Molecular Weight347.282429433
IUPAC Name2-aminoethyl (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoate
Traditional Namevirodhamine
CAS Registry Number443129-35-9
SMILES
CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(=O)OCCN
InChI Identifier
InChI=1S/C22H37NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-22(24)25-21-20-23/h6-7,9-10,12-13,15-16H,2-5,8,11,14,17-21,23H2,1H3/b7-6-,10-9-,13-12-,16-15-
InChI KeyDLHLOYYQQGSXCC-DOFZRALJSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acid esters
Direct ParentFatty acid esters
Alternative Parents
Substituents
  • Fatty acid ester
  • Amino acid or derivatives
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Primary aliphatic amine
  • Organopnictogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Process
Role
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 Solubility0.00013 g/LALOGPS
logP6.27ALOGPS
logP5.94ChemAxon
logS-6.4ALOGPS
pKa (Strongest Basic)9.23ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area52.32 ŲChemAxon
Rotatable Bond Count17ChemAxon
Refractivity112.67 m³·mol⁻¹ChemAxon
Polarizability42.97 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+197.13931661259
DarkChem[M-H]-196.73131661259
DeepCCS[M+H]+191.64330932474
DeepCCS[M-H]-189.28530932474
DeepCCS[M-2H]-222.46930932474
DeepCCS[M+Na]+197.9230932474
AllCCS[M+H]+193.832859911
AllCCS[M+H-H2O]+191.232859911
AllCCS[M+NH4]+196.232859911
AllCCS[M+Na]+196.932859911
AllCCS[M-H]-192.132859911
AllCCS[M+Na-2H]-194.432859911
AllCCS[M+HCOO]-197.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
O-Arachidonoyl EthanolamineCCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(=O)OCCN3095.1Standard polar33892256
O-Arachidonoyl EthanolamineCCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(=O)OCCN2378.1Standard non polar33892256
O-Arachidonoyl EthanolamineCCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(=O)OCCN2653.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
O-Arachidonoyl Ethanolamine,1TMS,isomer #1CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)OCCN[Si](C)(C)C2774.4Semi standard non polar33892256
O-Arachidonoyl Ethanolamine,1TMS,isomer #1CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)OCCN[Si](C)(C)C2737.3Standard non polar33892256
O-Arachidonoyl Ethanolamine,1TMS,isomer #1CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)OCCN[Si](C)(C)C3064.0Standard polar33892256
O-Arachidonoyl Ethanolamine,2TMS,isomer #1CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)OCCN([Si](C)(C)C)[Si](C)(C)C2978.6Semi standard non polar33892256
O-Arachidonoyl Ethanolamine,2TMS,isomer #1CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)OCCN([Si](C)(C)C)[Si](C)(C)C2895.5Standard non polar33892256
O-Arachidonoyl Ethanolamine,2TMS,isomer #1CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)OCCN([Si](C)(C)C)[Si](C)(C)C2898.3Standard polar33892256
O-Arachidonoyl Ethanolamine,1TBDMS,isomer #1CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)OCCN[Si](C)(C)C(C)(C)C2971.9Semi standard non polar33892256
O-Arachidonoyl Ethanolamine,1TBDMS,isomer #1CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)OCCN[Si](C)(C)C(C)(C)C2937.1Standard non polar33892256
O-Arachidonoyl Ethanolamine,1TBDMS,isomer #1CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)OCCN[Si](C)(C)C(C)(C)C3072.9Standard polar33892256
O-Arachidonoyl Ethanolamine,2TBDMS,isomer #1CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)OCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3412.6Semi standard non polar33892256
O-Arachidonoyl Ethanolamine,2TBDMS,isomer #1CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)OCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3189.2Standard non polar33892256
O-Arachidonoyl Ethanolamine,2TBDMS,isomer #1CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)OCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2938.8Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - O-Arachidonoyl Ethanolamine GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-9160000000-e4d605556a74c32850b52017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - O-Arachidonoyl Ethanolamine 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 - O-Arachidonoyl Ethanolamine 10V, Positive-QTOFsplash10-0005-6159000000-99134b0a76bda27146bc2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - O-Arachidonoyl Ethanolamine 20V, Positive-QTOFsplash10-0006-9241000000-24b121d519022021b0412017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - O-Arachidonoyl Ethanolamine 40V, Positive-QTOFsplash10-0006-9230000000-34e0714a863ac0a11fe42017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - O-Arachidonoyl Ethanolamine 10V, Negative-QTOFsplash10-000b-2049000000-44ec5ce62678fce7c9912017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - O-Arachidonoyl Ethanolamine 20V, Negative-QTOFsplash10-000j-5097000000-226c63be9164349ed9bf2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - O-Arachidonoyl Ethanolamine 40V, Negative-QTOFsplash10-0006-9030000000-f393ed4f36b8e090cc1a2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - O-Arachidonoyl Ethanolamine 10V, Positive-QTOFsplash10-0002-4329000000-2afbe38e34d21b7d29ed2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - O-Arachidonoyl Ethanolamine 20V, Positive-QTOFsplash10-01po-9412000000-2d595dbad447acf1e2662021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - O-Arachidonoyl Ethanolamine 40V, Positive-QTOFsplash10-00l6-9500000000-37b7a889796f7361f97e2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - O-Arachidonoyl Ethanolamine 10V, Negative-QTOFsplash10-0002-0029000000-6d820b2c37cd6bf13b7e2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - O-Arachidonoyl Ethanolamine 20V, Negative-QTOFsplash10-0f7a-5189000000-c237f01fc5e28353b3692021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - O-Arachidonoyl Ethanolamine 40V, Negative-QTOFsplash10-0uk9-9385000000-ece22a403f9d3abaf5f12021-09-24Wishart LabView Spectrum
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 IDFDB029625
KNApSAcK IDNot Available
Chemspider ID4650158
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkVirodhamine
METLIN IDNot Available
PubChem Compound5712057
PDB IDNot Available
ChEBI ID418207
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents 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.