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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2011-07-12 10:28:56 UTC
Update Date2022-03-07 02:51:34 UTC
HMDB IDHMDB0013659
Secondary Accession Numbers
  • HMDB13659
Metabolite Identification
Common Name(±)8(9)-EET Ethanolamide
Description(±)8(9)-EET ethanolamide is a cytochrome P450 (CYP450) metabolite of arachidonoyl ethanolamide (AEA), although specific stereochemistry rather than a racemic mixture would likely ensue from enzymatic metabolism (PMID: 17272674 ). AEA is an endogenous lipid neurotransmitter with cannabingeric activity, binding to both the central cannabinoid (CB1) and peripheral cannabinoid (CB2) receptors (PMID: 8395053 , 16078824 ). Fatty acid amide hydrolase (FAAH) is the enzyme responsible for the hydrolysis and inactivation of AEA (PMID: 12052036 ). Metabolism of AEA by COX-2, lipoxygenases, and CYP450 enzymes has also been documented (PMID: 12052037 , 17272674 ). Human liver microsomes metabolize AEA to 5,6-, 8,9-, 11,12-, and 14,15-EET ethanolamides in a time and protein concentration dependent manner (PMID: 17272674 ). (±)8(9)-EET reduces glomerular filtration rate through cyclooxygenase dependent preglomerular vasoconstriction (PMID: 1928373 ). The physiological actions of (±)8(9)-EET ethanolamide have not been examined.
Structure
Data?1582753141
Synonyms
ValueSource
8(9)-EET-eaChEBI
8(9)-EpETrE-eaChEBI
8,9-EET-eaChEBI
N-(8,9-Epoxy-5Z,11Z,14Z-eicosatrienoyl)-ethanolamineChEBI
N-(8,9-Epoxy-5Z,11Z,14Z-icosatrienoyl)ethanolamineChEBI
(+/-)8(9)-epetre ethanolamideHMDB
Chemical FormulaC22H37NO3
Average Molecular Weight363.5341
Monoisotopic Molecular Weight363.277344055
IUPAC Name(5Z)-N-(2-hydroxyethyl)-7-{3-[(2Z,5Z)-undeca-2,5-dien-1-yl]oxiran-2-yl}hept-5-enamide
Traditional Name8(9)-EpETrE-EA
CAS Registry NumberNot Available
SMILES
CCCCC\C=C/C\C=C/CC1OC1C\C=C/CCCC(=O)NCCO
InChI Identifier
InChI=1S/C22H37NO3/c1-2-3-4-5-6-7-8-9-12-15-20-21(26-20)16-13-10-11-14-17-22(25)23-18-19-24/h6-7,9-10,12-13,20-21,24H,2-5,8,11,14-19H2,1H3,(H,23,25)/b7-6-,12-9-,13-10-
InChI KeyBXHPMUQFGGSDAK-TYAUOURKSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as n-acylethanolamines. N-acylethanolamines are compounds containing an N-acyethanolamine moiety, which is characterized by an acyl group is linked to the nitrogen atom of ethanolamine.
KingdomOrganic compounds
Super ClassOrganic nitrogen compounds
ClassOrganonitrogen compounds
Sub ClassAmines
Direct ParentN-acylethanolamines
Alternative Parents
Substituents
  • N-acylethanolamine
  • Fatty amide
  • N-acyl-amine
  • Fatty acyl
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Oxacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Dialkyl ether
  • Oxirane
  • Ether
  • Organopnictogen compound
  • Alcohol
  • Organic oxygen compound
  • Organooxygen compound
  • Primary alcohol
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location

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 Solubility0.00085 g/LALOGPS
logP5.42ALOGPS
logP4.38ChemAxon
logS-5.6ALOGPS
pKa (Strongest Acidic)15.33ChemAxon
pKa (Strongest Basic)-0.34ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area61.86 ŲChemAxon
Rotatable Bond Count16ChemAxon
Refractivity111.37 m³·mol⁻¹ChemAxon
Polarizability44.21 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+195.75131661259
DarkChem[M-H]-193.71331661259
DeepCCS[M+H]+192.20430932474
DeepCCS[M-H]-189.84630932474
DeepCCS[M-2H]-222.87830932474
DeepCCS[M+Na]+198.37630932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(??)8(9)-EET EthanolamideCCCCC\C=C/C\C=C/CC1OC1C\C=C/CCCC(=O)NCCO3254.4Standard polar33892256
(??)8(9)-EET EthanolamideCCCCC\C=C/C\C=C/CC1OC1C\C=C/CCCC(=O)NCCO2678.0Standard non polar33892256
(??)8(9)-EET EthanolamideCCCCC\C=C/C\C=C/CC1OC1C\C=C/CCCC(=O)NCCO3011.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
(??)8(9)-EET Ethanolamide,1TMS,isomer #1CCCCC/C=C\C/C=C\CC1OC1C/C=C\CCCC(=O)NCCO[Si](C)(C)C2985.7Semi standard non polar33892256
(??)8(9)-EET Ethanolamide,1TMS,isomer #2CCCCC/C=C\C/C=C\CC1OC1C/C=C\CCCC(=O)N(CCO)[Si](C)(C)C2911.3Semi standard non polar33892256
(±)8(9)-EET Ethanolamide,2TMS,isomer #1CCCCC/C=C\C/C=C\CC1OC1C/C=C\CCCC(=O)N(CCO[Si](C)(C)C)[Si](C)(C)C2940.6Semi standard non polar33892256
(±)8(9)-EET Ethanolamide,2TMS,isomer #1CCCCC/C=C\C/C=C\CC1OC1C/C=C\CCCC(=O)N(CCO[Si](C)(C)C)[Si](C)(C)C3020.2Standard non polar33892256
(±)8(9)-EET Ethanolamide,2TMS,isomer #1CCCCC/C=C\C/C=C\CC1OC1C/C=C\CCCC(=O)N(CCO[Si](C)(C)C)[Si](C)(C)C3097.0Standard polar33892256
(??)8(9)-EET Ethanolamide,1TBDMS,isomer #1CCCCC/C=C\C/C=C\CC1OC1C/C=C\CCCC(=O)NCCO[Si](C)(C)C(C)(C)C3220.9Semi standard non polar33892256
(??)8(9)-EET Ethanolamide,1TBDMS,isomer #2CCCCC/C=C\C/C=C\CC1OC1C/C=C\CCCC(=O)N(CCO)[Si](C)(C)C(C)(C)C3139.1Semi standard non polar33892256
(±)8(9)-EET Ethanolamide,2TBDMS,isomer #1CCCCC/C=C\C/C=C\CC1OC1C/C=C\CCCC(=O)N(CCO[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3430.2Semi standard non polar33892256
(±)8(9)-EET Ethanolamide,2TBDMS,isomer #1CCCCC/C=C\C/C=C\CC1OC1C/C=C\CCCC(=O)N(CCO[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3367.9Standard non polar33892256
(±)8(9)-EET Ethanolamide,2TBDMS,isomer #1CCCCC/C=C\C/C=C\CC1OC1C/C=C\CCCC(=O)N(CCO[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3151.2Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - (±)8(9)-EET Ethanolamide GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f6t-7975000000-138caba1cc10d88b3acb2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (±)8(9)-EET Ethanolamide GC-MS (1 TMS) - 70eV, Positivesplash10-0fk9-8895200000-ff0d605a4780f0fe8a9b2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (±)8(9)-EET Ethanolamide 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 - (±)8(9)-EET Ethanolamide 10V, Positive-QTOFsplash10-03di-4219000000-6a4153a00d35175f07cc2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)8(9)-EET Ethanolamide 20V, Positive-QTOFsplash10-03di-9501000000-49546729e6f1fc39fbde2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)8(9)-EET Ethanolamide 40V, Positive-QTOFsplash10-03di-9300000000-e83b610335b0f604ffa22017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)8(9)-EET Ethanolamide 10V, Negative-QTOFsplash10-03di-0209000000-ecb21063dfd7ef100dad2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)8(9)-EET Ethanolamide 20V, Negative-QTOFsplash10-03dl-5309000000-6e6597f4aa6f9be887a12017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)8(9)-EET Ethanolamide 40V, Negative-QTOFsplash10-01ox-9400000000-a6384c85eb3f6a7860502017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)8(9)-EET Ethanolamide 10V, Positive-QTOFsplash10-03di-5209000000-53d5fe289aac0a214cf62021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)8(9)-EET Ethanolamide 20V, Positive-QTOFsplash10-03dm-9103000000-2718f725d05698a31a6a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)8(9)-EET Ethanolamide 40V, Positive-QTOFsplash10-000x-9100000000-3f90e9cfac2f109888672021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)8(9)-EET Ethanolamide 10V, Negative-QTOFsplash10-03di-0009000000-98c48b1fa4d3ad7800222021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)8(9)-EET Ethanolamide 20V, Negative-QTOFsplash10-03dl-2129000000-908411b9c587439538412021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)8(9)-EET Ethanolamide 40V, Negative-QTOFsplash10-0596-9202000000-f292ca66393a75a3a56a2021-09-22Wishart 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 IDFDB029629
KNApSAcK IDNot Available
Chemspider ID17220861
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound16061182
PDB IDNot Available
ChEBI ID136989
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. Kozak KR, Marnett LJ: Oxidative metabolism of endocannabinoids. Prostaglandins Leukot Essent Fatty Acids. 2002 Feb-Mar;66(2-3):211-20. [PubMed:12052037 ]
  2. Snider NT, Kornilov AM, Kent UM, Hollenberg PF: Anandamide metabolism by human liver and kidney microsomal cytochrome p450 enzymes to form hydroxyeicosatetraenoic and epoxyeicosatrienoic acid ethanolamides. J Pharmacol Exp Ther. 2007 May;321(2):590-7. Epub 2007 Feb 1. [PubMed:17272674 ]
  3. Felder CC, Briley EM, Axelrod J, Simpson JT, Mackie K, Devane WA: Anandamide, an endogenous cannabimimetic eicosanoid, binds to the cloned human cannabinoid receptor and stimulates receptor-mediated signal transduction. Proc Natl Acad Sci U S A. 1993 Aug 15;90(16):7656-60. [PubMed:8395053 ]
  4. Lambert DM, Fowler CJ: The endocannabinoid system: drug targets, lead compounds, and potential therapeutic applications. J Med Chem. 2005 Aug 11;48(16):5059-87. [PubMed:16078824 ]
  5. Deutsch DG, Ueda N, Yamamoto S: The fatty acid amide hydrolase (FAAH). Prostaglandins Leukot Essent Fatty Acids. 2002 Feb-Mar;66(2-3):201-10. [PubMed:12052036 ]
  6. Katoh T, Takahashi K, Capdevila J, Karara A, Falck JR, Jacobson HR, Badr KF: Glomerular stereospecific synthesis and hemodynamic actions of 8,9-epoxyeicosatrienoic acid in rat kidney. Am J Physiol. 1991 Oct;261(4 Pt 2):F578-86. [PubMed:1928373 ]