Record Information
Version1.0
Creation date2011-09-21 01:58:21 UTC
Update date2018-05-28 18:38:34 UTC
Primary IDFDB029607
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name20-HETE ethanolamide
Description20-HETE ethanolamide is a N-acylethanolamine. N-acylethanolamines (NAEs) constitute a class of lipid compounds naturally present in both animal and plant membranes as constituents of the membrane-bound phospholipid, N-acylphosphatidylethanolamine (NAPE). NAPE is composed of a third fatty acid moiety linked to the amino head group of the commonly occurring membrane phospholipid, phosphatidylethanolamine. NAEs are released from NAPE by phospholipase D-type hydrolases in response to a variety of stimuli. Transient NAE release and accumulation has been attributed a variety of biological activities, including neurotransmission, membrane protection, and immunomodulation in animals. N-oleoylethanolamine is an inhibitor of the sphingolipid signaling pathway, via specific ceramidase inhibition (ceramidase converts ceramide to sphingosine). N-oleoylethanolamine blocks the effects of TNF- and arachidonic acid on intracellular Ca concentration. (PMID: 12692337, 12056855, 12560208, 11997249) [HMDB]
CAS Number942069-11-6
Structure
Thumb
Synonyms
SynonymSource
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
20-HETE EAhmdb
20-HETE-EAhmdb
20-hydroxy AEAhmdb
20-hydroxy arachidonoyl ethanolamidehmdb
20-hydroxyepoxyeicosatrienoatehmdb
20-hydroxyepoxyeicosatrienoic acidhmdb
20-hydroxyepoxyeicosatrienoic acid ethanolamidehmdb
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC22H37NO3
IUPAC name(5Z,8Z,11Z,14Z)-20-hydroxy-N-(2-hydroxyethyl)icosa-5,8,11,14-tetraenamide
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
Isomeric SMILESOCCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(=O)NCCO
Average Molecular Weight363.5341
Monoisotopic Molecular Weight363.277344055
Classification
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
Ontology
Disposition

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS20-HETE ethanolamide, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0j59-3589000000-3b2241d486c86688ef75Spectrum
Predicted GC-MS20-HETE ethanolamide, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0fdo-5439700000-2ce10d8e6ec266bf7497Spectrum
Predicted GC-MS20-HETE ethanolamide, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dj-3019000000-f2029ffb36e80f0831faSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dl-9023000000-b8b72230e0c2ee44dd70Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dl-9131000000-46f2377e1f133b01723bSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0009000000-f110e36f00b594851805Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03dl-3009000000-83198bcf34c23d1f14afSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9011000000-a8fbb4764172356595f9Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0009000000-9e3358e490a06a8fff0cSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-3119000000-5a324625cccf8671a86fSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9003000000-97c2fbd008005d741243Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-7219000000-ae8a82a0373146ed1cdaSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dl-9001000000-0044622ae985419b2409Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-9300000000-46979c19002f897fe2edSpectrum
NMRNot Available
ChemSpider ID21467685
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID35027640
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB13630
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
FoodReference
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