Dihomo-gamma-Linolenoyl ethanolamide (CHEM041390)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-27 01:26:33 UTC
Update Date2016-11-09 01:22:28 UTC
Accession NumberCHEM041390
Identification
Common NameDihomo-gamma-Linolenoyl ethanolamide
ClassSmall Molecule
Description
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
8,11,14-EicosatrienoylethanolamideChEBI
Anandamide (20.3,N-6)ChEBI
HGLEAChEBI
Homo-gamma-linolenylethanolamideChEBI
N-(8Z,11Z,14Z-Eicosatrienoyl)-ethanolamineChEBI
N-(8Z,11Z,14Z-Icosatrienoyl)-ethanolamideChEBI
Homo-g-linolenylethanolamideGenerator
Homo-γ-linolenylethanolamideGenerator
Dihomo-g-linolenoylethanolamideGenerator
Dihomo-γ-linolenoylethanolamideGenerator
Homo-gamma-linolenoyl ethanolamideMeSH
dihomo-g-Linolenoyl ethanolamideGenerator, HMDB
dihomo-γ-linolenoyl ethanolamideGenerator, HMDB
(8Z,11Z,14Z)-N-(2-Hydroxyethyl)icosa-8,11,14-trienamideHMDB
DGLA eaHMDB
dihomo-gamma-Linolenoylethanol amideHMDB
Dihomo-g-linolenoyl-eaGenerator
Dihomo-γ-linolenoyl-eaGenerator
Chemical FormulaC22H39NO2
Average Molecular Mass349.551 g/mol
Monoisotopic Mass349.298 g/mol
CAS Registry Number150314-34-4
IUPAC Name(8Z,11Z,14Z)-N-(2-hydroxyethyl)icosa-8,11,14-trienamide
Traditional Namehglea
SMILESCCCCC\C=C/C\C=C/C\C=C/CCCCCCC(=O)NCCO
InChI IdentifierInChI=1S/C22H39NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-22(25)23-20-21-24/h6-7,9-10,12-13,24H,2-5,8,11,14-21H2,1H3,(H,23,25)/b7-6-,10-9-,13-12-
InChI KeyULQWKETUACYZLI-QNEBEIHSSA-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 Solubility0.00023 g/LALOGPS
logP6.28ALOGPS
logP5.68ChemAxon
logS-6.2ALOGPS
pKa (Strongest Acidic)15.45ChemAxon
pKa (Strongest Basic)-1.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area49.33 ŲChemAxon
Rotatable Bond Count17ChemAxon
Refractivity111.85 m³·mol⁻¹ChemAxon
Polarizability44.39 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-029g-8983000000-42e4744911acb250a34fSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00y0-9573200000-a8db30d9ff9f0147625eSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0w29-5149000000-90d7161272eec6776994Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dl-9121000000-76079fc33c97f5136a62Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dl-9230000000-71d39c754ceca5b22f18Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0009000000-70187c5620a575618c1eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01pk-5019000000-7d063e287364f13a7e93Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9010000000-756ebbaf8f5db95a9d3cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0009000000-25e88f7ed1f5fc19f31fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-5129000000-b4eff9f1d3f5b681b725Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9010000000-3b5498e873ffa2327ed5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0w29-9228000000-3de5ffd9870259f4c489Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dl-9000000000-55cab8b86efb0346a9efSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01ox-9100000000-50506e85794f343a8424Spectrum
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 IDHMDB0013625
FooDB IDFDB029602
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID4445443
ChEBI ID34488
PubChem Compound ID5282272
Kegg Compound IDC13828
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. 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.
2. 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.
3. 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.
4. 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.
5. Anton M, Rodriguez-Gonzalez A, Rodriguez-Rojo IC, Pastor A, Correas A, Serrano A, Ballesta A, Alen F, Gomez de Heras R, de la Torre R, Rodriguez de Fonseca F, Orio L: Increased plasma oleoylethanolamide and palmitoleoylethanolamide levels correlate with inflammatory changes in alcohol binge drinkers: the case of HMGB1 in women. Addict Biol. 2018 Nov;23(6):1242-1250. doi: 10.1111/adb.12580. Epub 2017 Nov 27.