20-HETE ethanolamide (CHEM041395)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-27 01:26:40 UTC
Update Date2016-11-09 01:22:28 UTC
Accession NumberCHEM041395
Identification
Common Name20-HETE ethanolamide
ClassSmall Molecule
DescriptionAn N-(polyunsaturated fatty acyl)ethanolamine that is anandamide in which one of the methyl hydrogens at position 20 has been replaced by a hydroxy group.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
20-HETE-eaChEBI
20-HETE-ethanolamineChEBI
20-Hydroxy-5,8,11,14-eicosatetraenoic acid ethanolamideChEBI
20-Hydroxy-5,8,11,14-icosatetraenoic acid ethanolamideChEBI
20-HydroxyanandamideChEBI
20-Hydroxyarachidonic acid ethanolamideChEBI
N-(20-Hydroxy-5Z,8Z,11Z,14Z-eicosatetraenoyl)-ethanolamineChEBI
N-(20-Hydroxy-5Z,8Z,11Z,14Z-icosatetraenoyl)ethanolamineChEBI
N-[5Z,8Z,11Z,14Z-20-Hydroxyicosatetraenoyl]ethanolamineChEBI
20-Hydroxy-5,8,11,14-eicosatetraenoate ethanolamideGenerator
20-Hydroxy-5,8,11,14-icosatetraenoate ethanolamideGenerator
20-Hydroxyarachidonate ethanolamideGenerator
20-HETE eaHMDB
20-Hydroxy aeaHMDB
20-Hydroxy arachidonoyl ethanolamideHMDB
20-HydroxyepoxyeicosatrienoateHMDB
20-Hydroxyepoxyeicosatrienoic acidHMDB
20-Hydroxyepoxyeicosatrienoic acid ethanolamideHMDB
Chemical FormulaC22H37NO3
Average Molecular Mass363.534 g/mol
Monoisotopic Mass363.277 g/mol
CAS Registry NumberNot Available
IUPAC Name(5Z,8Z,11Z,14Z)-20-hydroxy-N-(2-hydroxyethyl)icosa-5,8,11,14-tetraenamide
Traditional Name20-hete-EA
SMILESOCCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(=O)NCCO
InChI IdentifierInChI=1S/C22H37NO3/c24-20-17-15-13-11-9-7-5-3-1-2-4-6-8-10-12-14-16-18-22(26)23-19-21-25/h1,3-4,6-7,9-10,12,24-25H,2,5,8,11,13-21H2,(H,23,26)/b3-1-,6-4-,9-7-,12-10-
InChI KeyQRMZDMUHHZLRMH-DTLRTWKJSA-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
  • Carboxylic acid derivative
  • Alcohol
  • Organooxygen compound
  • Primary alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic 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 Solubility0.0028 g/LALOGPS
logP4.88ALOGPS
logP3.88ChemAxon
logS-5.1ALOGPS
pKa (Strongest Acidic)15.44ChemAxon
pKa (Strongest Basic)-1.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area69.56 ŲChemAxon
Rotatable Bond Count17ChemAxon
Refractivity114.89 m³·mol⁻¹ChemAxon
Polarizability44.19 ųChemAxon
Number of Rings0ChemAxon
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, Positivesplash10-0j59-3589000000-3b2241d486c86688ef75Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0fdo-5439700000-2ce10d8e6ec266bf7497Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dj-3019000000-f2029ffb36e80f0831faSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dl-9023000000-b8b72230e0c2ee44dd70Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dl-9131000000-46f2377e1f133b01723bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0009000000-f110e36f00b594851805Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03dl-3009000000-83198bcf34c23d1f14afSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9011000000-a8fbb4764172356595f9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0009000000-9e3358e490a06a8fff0cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-3119000000-5a324625cccf8671a86fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9003000000-97c2fbd008005d741243Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-7219000000-ae8a82a0373146ed1cdaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dl-9001000000-0044622ae985419b2409Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-9300000000-46979c19002f897fe2edSpectrum
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 IDHMDB0013630
FooDB IDFDB029607
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID21467685
ChEBI ID136992
PubChem Compound ID35027640
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=17272674
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=18698000
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=21289075
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=21689782
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=27000802
6. Tripathy S, Kleppinger-Sparace K, Dixon RA, Chapman KD: N-acylethanolamine signaling in tobacco is mediated by a membrane-associated, high-affinity binding protein. Plant Physiol. 2003 Apr;131(4):1781-91.
7. Lecour S, Smith RM, Woodward B, Opie LH, Rochette L, Sack MN: Identification of a novel role for sphingolipid signaling in TNF alpha and ischemic preconditioning mediated cardioprotection. J Mol Cell Cardiol. 2002 May;34(5):509-18.
8. Hofmann U, Domeier E, Frantz S, Laser M, Weckler B, Kuhlencordt P, Heuer S, Keweloh B, Ertl G, Bonz AW: Increased myocardial oxygen consumption by TNF-alpha is mediated by a sphingosine signaling pathway. Am J Physiol Heart Circ Physiol. 2003 Jun;284(6):H2100-5. Epub 2003 Jan 30.
9. Amadou A, Nawrocki A, Best-Belpomme M, Pavoine C, Pecker F: Arachidonic acid mediates dual effect of TNF-alpha on Ca2+ transients and contraction of adult rat cardiomyocytes. Am J Physiol Cell Physiol. 2002 Jun;282(6):C1339-47.