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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2010-05-20 10:35:33 UTC
Update Date2022-03-07 02:51:33 UTC
HMDB IDHMDB0013624
Secondary Accession Numbers
  • HMDB13624
Metabolite Identification
Common NameAlpha-Linolenoyl ethanolamide
Descriptionalpha-Linolenoyl 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 ).
Structure
Data?1582753137
Synonyms
ValueSource
a-Linolenoyl ethanolamideGenerator
Α-linolenoyl ethanolamideGenerator
Linoleoyl ethanolamideChEMBL, HMDB
alpha-LEAHMDB
N-cis-9,12,15-OctadecatrienoylethanolamineHMDB
ALEA compoundMeSH, HMDB
alpha-Linolenoyl ethanolamideMeSH
Chemical FormulaC20H35NO2
Average Molecular Weight321.4974
Monoisotopic Molecular Weight321.266779369
IUPAC Name(9Z,12Z,15Z)-N-(2-hydroxyethyl)octadeca-9,12,15-trienamide
Traditional Name(9Z,12Z,15Z)-N-(2-hydroxyethyl)octadeca-9,12,15-trienamide
CAS Registry NumberNot Available
SMILES
CC\C=C/C\C=C/C\C=C/CCCCCCCC(=O)NCCO
InChI Identifier
InChI=1S/C20H35NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-20(23)21-18-19-22/h3-4,6-7,9-10,22H,2,5,8,11-19H2,1H3,(H,21,23)/b4-3-,7-6-,10-9-
InChI KeyHBJXRRXWHSHZPU-PDBXOOCHSA-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 Solubility0.001 g/LALOGPS
logP5.6ALOGPS
logP4.79ChemAxon
logS-5.5ALOGPS
pKa (Strongest Acidic)15.47ChemAxon
pKa (Strongest Basic)-0.33ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area49.33 ŲChemAxon
Rotatable Bond Count15ChemAxon
Refractivity102.65 m³·mol⁻¹ChemAxon
Polarizability40.15 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+185.4331661259
DarkChem[M-H]-185.05831661259
DeepCCS[M+H]+186.67630932474
DeepCCS[M-H]-184.31830932474
DeepCCS[M-2H]-217.20530932474
DeepCCS[M+Na]+192.76930932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Alpha-Linolenoyl ethanolamideCC\C=C/C\C=C/C\C=C/CCCCCCCC(=O)NCCO3230.5Standard polar33892256
Alpha-Linolenoyl ethanolamideCC\C=C/C\C=C/C\C=C/CCCCCCCC(=O)NCCO2468.1Standard non polar33892256
Alpha-Linolenoyl ethanolamideCC\C=C/C\C=C/C\C=C/CCCCCCCC(=O)NCCO2679.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Alpha-Linolenoyl ethanolamide,1TMS,isomer #1CC/C=C\C/C=C\C/C=C\CCCCCCCC(=O)NCCO[Si](C)(C)C2676.9Semi standard non polar33892256
Alpha-Linolenoyl ethanolamide,1TMS,isomer #2CC/C=C\C/C=C\C/C=C\CCCCCCCC(=O)N(CCO)[Si](C)(C)C2633.0Semi standard non polar33892256
Alpha-Linolenoyl ethanolamide,2TMS,isomer #1CC/C=C\C/C=C\C/C=C\CCCCCCCC(=O)N(CCO[Si](C)(C)C)[Si](C)(C)C2669.0Semi standard non polar33892256
Alpha-Linolenoyl ethanolamide,2TMS,isomer #1CC/C=C\C/C=C\C/C=C\CCCCCCCC(=O)N(CCO[Si](C)(C)C)[Si](C)(C)C2731.9Standard non polar33892256
Alpha-Linolenoyl ethanolamide,2TMS,isomer #1CC/C=C\C/C=C\C/C=C\CCCCCCCC(=O)N(CCO[Si](C)(C)C)[Si](C)(C)C2830.5Standard polar33892256
Alpha-Linolenoyl ethanolamide,1TBDMS,isomer #1CC/C=C\C/C=C\C/C=C\CCCCCCCC(=O)NCCO[Si](C)(C)C(C)(C)C2918.4Semi standard non polar33892256
Alpha-Linolenoyl ethanolamide,1TBDMS,isomer #2CC/C=C\C/C=C\C/C=C\CCCCCCCC(=O)N(CCO)[Si](C)(C)C(C)(C)C2852.8Semi standard non polar33892256
Alpha-Linolenoyl ethanolamide,2TBDMS,isomer #1CC/C=C\C/C=C\C/C=C\CCCCCCCC(=O)N(CCO[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3158.8Semi standard non polar33892256
Alpha-Linolenoyl ethanolamide,2TBDMS,isomer #1CC/C=C\C/C=C\C/C=C\CCCCCCCC(=O)N(CCO[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3087.9Standard non polar33892256
Alpha-Linolenoyl ethanolamide,2TBDMS,isomer #1CC/C=C\C/C=C\C/C=C\CCCCCCCC(=O)N(CCO[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2897.2Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Alpha-Linolenoyl ethanolamide GC-MS (Non-derivatized) - 70eV, Positivesplash10-01ot-3960000000-226ecbd1b70d86c5d3fe2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Alpha-Linolenoyl ethanolamide GC-MS (1 TMS) - 70eV, Positivesplash10-00dj-9664000000-ad5a0bcf746ff0c9f2532017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Alpha-Linolenoyl ethanolamide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Alpha-Linolenoyl ethanolamide 10V, Positive-QTOFsplash10-00di-0009000000-1e9fdf4410a883c289492021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Alpha-Linolenoyl ethanolamide 20V, Positive-QTOFsplash10-0n9v-9644000000-a75202b20bb446a4cfda2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Alpha-Linolenoyl ethanolamide 20V, Positive-QTOFsplash10-0i7m-9644000000-f11332b1cc1fa38692fa2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Alpha-Linolenoyl ethanolamide 40V, Positive-QTOFsplash10-005c-9000000000-2c9af53cbc535abe705d2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alpha-Linolenoyl ethanolamide 10V, Positive-QTOFsplash10-0229-6159000000-94057d6cc19761ecbccd2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alpha-Linolenoyl ethanolamide 20V, Positive-QTOFsplash10-03dl-9120000000-9388d7c84f3083f8cd562017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alpha-Linolenoyl ethanolamide 40V, Positive-QTOFsplash10-03di-9210000000-119fd7ae8ce73abb4f882017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alpha-Linolenoyl ethanolamide 10V, Negative-QTOFsplash10-00di-0029000000-d0f5f7309a8af700f9232017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alpha-Linolenoyl ethanolamide 20V, Negative-QTOFsplash10-0h93-8079000000-d6f0c40f18d74d1b3ef42017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alpha-Linolenoyl ethanolamide 40V, Negative-QTOFsplash10-0006-9010000000-eae31bc3ee94bdd982152017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alpha-Linolenoyl ethanolamide 10V, Negative-QTOFsplash10-00di-0019000000-60eaea70585d78109afb2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alpha-Linolenoyl ethanolamide 20V, Negative-QTOFsplash10-00di-5139000000-30c4ca9390a8dd0574292021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alpha-Linolenoyl ethanolamide 40V, Negative-QTOFsplash10-052f-9010000000-3432f4d3ac3a1fc3def92021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alpha-Linolenoyl ethanolamide 10V, Positive-QTOFsplash10-0229-9127000000-65d40f108a9454c055f82021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alpha-Linolenoyl ethanolamide 20V, Positive-QTOFsplash10-03dl-9000000000-8f2f6fdda3afa6267e402021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alpha-Linolenoyl ethanolamide 40V, Positive-QTOFsplash10-01ox-9100000000-79e84dade50d1194d9552021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.118 +/- 0.069 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 IDFDB029601
KNApSAcK IDNot Available
Chemspider ID4446569
KEGG Compound IDC13828
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5283449
PDB IDNot Available
ChEBI ID613508
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 ]