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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2010-05-20 10:41:07 UTC
Update Date2022-03-07 02:51:34 UTC
HMDB IDHMDB0013625
Secondary Accession Numbers
  • HMDB13625
Metabolite Identification
Common NameDihomo-gamma-linolenoylethanolamide
DescriptionDihomo-gamma-linolenoylethanolamide (DGLEA) is an 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 have been attributed to a variety of biological activities, including neurotransmission, membrane protection, and immunomodulation in animals. During abstinence, young adults with a history of alcohol binge drinking had elevated plasma levels of monounsaturated and polyunsaturatedacylethanolamides, specifically oleoylethanolamide (OEA), palmitoleoylethanolamide (POEA), arachidonoylethanolamide (AEA), and dihomo-gamma-linolenoylethanolamide (DGLEA). Changes in these lipids positively correlated with mRNA upregulation of inflammatory markers in peripheral blood mononuclear cells (PBMCs), such as toll-like receptors (TLR4), pro-inflammatory cytokines/chemokines, and cyclooxygenase-2 (PMID: 29178411 ).
Structure
Data?1582753137
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 Weight349.5506
Monoisotopic Molecular Weight349.298079497
IUPAC Name(8Z,11Z,14Z)-N-(2-hydroxyethyl)icosa-8,11,14-trienamide
Traditional Namehglea
CAS Registry Number150314-34-4
SMILES
CCCCC\C=C/C\C=C/C\C=C/CCCCCCC(=O)NCCO
InChI Identifier
InChI=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
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 Solubility0.00023 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
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+196.92431661259
DarkChem[M-H]-196.78831661259
DeepCCS[M+H]+197.63930932474
DeepCCS[M-H]-195.28130932474
DeepCCS[M-2H]-228.16830932474
DeepCCS[M+Na]+203.73230932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Dihomo-gamma-linolenoylethanolamideCCCCC\C=C/C\C=C/C\C=C/CCCCCCC(=O)NCCO3260.3Standard polar33892256
Dihomo-gamma-linolenoylethanolamideCCCCC\C=C/C\C=C/C\C=C/CCCCCCC(=O)NCCO2634.1Standard non polar33892256
Dihomo-gamma-linolenoylethanolamideCCCCC\C=C/C\C=C/C\C=C/CCCCCCC(=O)NCCO2862.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Dihomo-gamma-linolenoylethanolamide,1TMS,isomer #1CCCCC/C=C\C/C=C\C/C=C\CCCCCCC(=O)NCCO[Si](C)(C)C2879.5Semi standard non polar33892256
Dihomo-gamma-linolenoylethanolamide,1TMS,isomer #2CCCCC/C=C\C/C=C\C/C=C\CCCCCCC(=O)N(CCO)[Si](C)(C)C2826.4Semi standard non polar33892256
Dihomo-gamma-linolenoylethanolamide,2TMS,isomer #1CCCCC/C=C\C/C=C\C/C=C\CCCCCCC(=O)N(CCO[Si](C)(C)C)[Si](C)(C)C2867.1Semi standard non polar33892256
Dihomo-gamma-linolenoylethanolamide,2TMS,isomer #1CCCCC/C=C\C/C=C\C/C=C\CCCCCCC(=O)N(CCO[Si](C)(C)C)[Si](C)(C)C2914.9Standard non polar33892256
Dihomo-gamma-linolenoylethanolamide,2TMS,isomer #1CCCCC/C=C\C/C=C\C/C=C\CCCCCCC(=O)N(CCO[Si](C)(C)C)[Si](C)(C)C2948.7Standard polar33892256
Dihomo-gamma-linolenoylethanolamide,1TBDMS,isomer #1CCCCC/C=C\C/C=C\C/C=C\CCCCCCC(=O)NCCO[Si](C)(C)C(C)(C)C3117.9Semi standard non polar33892256
Dihomo-gamma-linolenoylethanolamide,1TBDMS,isomer #2CCCCC/C=C\C/C=C\C/C=C\CCCCCCC(=O)N(CCO)[Si](C)(C)C(C)(C)C3059.8Semi standard non polar33892256
Dihomo-gamma-linolenoylethanolamide,2TBDMS,isomer #1CCCCC/C=C\C/C=C\C/C=C\CCCCCCC(=O)N(CCO[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3356.2Semi standard non polar33892256
Dihomo-gamma-linolenoylethanolamide,2TBDMS,isomer #1CCCCC/C=C\C/C=C\C/C=C\CCCCCCC(=O)N(CCO[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3247.7Standard non polar33892256
Dihomo-gamma-linolenoylethanolamide,2TBDMS,isomer #1CCCCC/C=C\C/C=C\C/C=C\CCCCCCC(=O)N(CCO[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3011.1Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Dihomo-gamma-linolenoylethanolamide GC-MS (Non-derivatized) - 70eV, Positivesplash10-029g-8983000000-42e4744911acb250a34f2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dihomo-gamma-linolenoylethanolamide GC-MS (1 TMS) - 70eV, Positivesplash10-00y0-9573200000-a8db30d9ff9f0147625e2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dihomo-gamma-linolenoylethanolamide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dihomo-gamma-linolenoylethanolamide 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 - Dihomo-gamma-linolenoylethanolamide 10V, Positive-QTOFsplash10-0w29-5149000000-90d7161272eec67769942017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihomo-gamma-linolenoylethanolamide 20V, Positive-QTOFsplash10-03dl-9121000000-76079fc33c97f5136a622017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihomo-gamma-linolenoylethanolamide 40V, Positive-QTOFsplash10-03dl-9230000000-71d39c754ceca5b22f182017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihomo-gamma-linolenoylethanolamide 10V, Negative-QTOFsplash10-0002-0009000000-70187c5620a575618c1e2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihomo-gamma-linolenoylethanolamide 20V, Negative-QTOFsplash10-01pk-5019000000-7d063e287364f13a7e932017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihomo-gamma-linolenoylethanolamide 40V, Negative-QTOFsplash10-0006-9010000000-756ebbaf8f5db95a9d3c2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihomo-gamma-linolenoylethanolamide 10V, Negative-QTOFsplash10-0002-0009000000-25e88f7ed1f5fc19f31f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihomo-gamma-linolenoylethanolamide 20V, Negative-QTOFsplash10-0002-5129000000-b4eff9f1d3f5b681b7252021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihomo-gamma-linolenoylethanolamide 40V, Negative-QTOFsplash10-052f-9010000000-3b5498e873ffa2327ed52021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihomo-gamma-linolenoylethanolamide 10V, Positive-QTOFsplash10-0w29-9228000000-3de5ffd9870259f4c4892021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihomo-gamma-linolenoylethanolamide 20V, Positive-QTOFsplash10-03dl-9000000000-55cab8b86efb0346a9ef2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihomo-gamma-linolenoylethanolamide 40V, Positive-QTOFsplash10-01ox-9100000000-50506e85794f343a84242021-09-23Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified1.01 +/- 0.48 uMAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB029602
KNApSAcK IDNot Available
Chemspider ID4445443
KEGG Compound IDC13828
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5282272
PDB IDNot Available
ChEBI ID34488
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. 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. [PubMed:12560208 ]
  2. 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. [PubMed:12692337 ]
  3. 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. [PubMed:12056855 ]
  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. [PubMed:11997249 ]
  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. [PubMed:29178411 ]