(±)-8(9)-EET ethanolamide (CHEM041415)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-27 01:28:29 UTC
Update Date2016-11-09 01:22:28 UTC
Accession NumberCHEM041415
Identification
Common Name(±)-8(9)-EET ethanolamide
ClassSmall Molecule
DescriptionAn N-(polyunsaturated fatty acyl)ethanolamine obtained by formal epoxidation across the 8,9-double bond of anandamide.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
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 Mass363.534 g/mol
Monoisotopic Mass363.277 g/mol
CAS Registry NumberNot Available
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
SMILESCCCCC\C=C/C\C=C/CC1OC1C\C=C/CCCC(=O)NCCO
InChI IdentifierInChI=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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted 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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f6t-7975000000-138caba1cc10d88b3acbSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0fk9-8895200000-ff0d605a4780f0fe8a9bSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-4219000000-6a4153a00d35175f07ccSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-9501000000-49546729e6f1fc39fbdeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-9300000000-e83b610335b0f604ffa2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0209000000-ecb21063dfd7ef100dadSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03dl-5309000000-6e6597f4aa6f9be887a1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01ox-9400000000-a6384c85eb3f6a786050Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-5209000000-53d5fe289aac0a214cf6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dm-9103000000-2718f725d05698a31a6aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000x-9100000000-3f90e9cfac2f10988867Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0009000000-98c48b1fa4d3ad780022Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03dl-2129000000-908411b9c58743953841Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0596-9202000000-f292ca66393a75a3a56aSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0013659
FooDB IDFDB029629
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID17220861
ChEBI ID136989
PubChem Compound ID16061182
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=20702771
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=21689782
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=27000802
4. 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.
5. 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.
6. 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.
7. 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.
8. Kozak KR, Marnett LJ: Oxidative metabolism of endocannabinoids. Prostaglandins Leukot Essent Fatty Acids. 2002 Feb-Mar;66(2-3):211-20.
9. 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.