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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2009-04-06 16:21:47 UTC
Update Date2022-03-07 02:51:22 UTC
HMDB IDHMDB0012252
Secondary Accession Numbers
  • HMDB12252
Metabolite Identification
Common NameLinoleoyl ethanolamide
DescriptionLinoleoyl ethanolamide, also known as linoleamide mea or anandamide (18:2, N-6), 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. Thus, linoleoyl ethanolamide is considered to be a fatty amide. Based on a literature review very few articles have been published on Linoleoyl ethanolamide.
Structure
Data?1582753033
Synonyms
ValueSource
(9Z,12Z)-N-(2-Hydroxyethyl)octadeca-9,12-dien-1-amideChEBI
Anandamide (18:2, N-6)ChEBI
Linoleamide meaChEBI
Linoleic ethanolamideChEBI
Linoleoyl monoethanolamideChEBI
Monoethanolamine linoleic acid amideChEBI
N-(2-Hydroxyethyl)-9,12-octadecadienamideChEBI
N-(2-Hydroxyethyl)linoleamideChEBI
N-(9Z,12Z-Octadecadienoyl)-ethanolamineChEBI
N-cis-9-cis-12-OctadecadienoylethanolamineChEBI
Monoethanolamine linoleate amideGenerator
LEAHMDB
N-(2-Hydroxyethyl)-linoleamideHMDB
LinoleoylethanolamideHMDB
Linoleoyl ethanolamideMeSH
Chemical FormulaC20H37NO2
Average Molecular Weight323.5133
Monoisotopic Molecular Weight323.282429433
IUPAC Name(9Z,12Z)-N-(2-hydroxyethyl)octadeca-9,12-dienamide
Traditional Namelinoleamide mea
CAS Registry Number68171-52-8
SMILES
CCCCC\C=C/C\C=C/CCCCCCCC(=O)NCCO
InChI Identifier
InChI=1S/C20H37NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-20(23)21-18-19-22/h6-7,9-10,22H,2-5,8,11-19H2,1H3,(H,21,23)/b7-6-,10-9-
InChI KeyKQXDGUVSAAQARU-HZJYTTRNSA-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

Source

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point499.06 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility0.11 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP6.003 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.00042 g/LALOGPS
logP6.26ALOGPS
logP5.15ChemAxon
logS-5.9ALOGPS
pKa (Strongest Acidic)15.47ChemAxon
pKa (Strongest Basic)-1.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area49.33 ŲChemAxon
Rotatable Bond Count16ChemAxon
Refractivity101.53 m³·mol⁻¹ChemAxon
Polarizability41.41 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+188.81831661259
DarkChem[M-H]-187.88631661259
DeepCCS[M+H]+191.38730932474
DeepCCS[M-H]-189.02930932474
DeepCCS[M-2H]-221.91630932474
DeepCCS[M+Na]+197.4830932474

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Linoleoyl ethanolamide,1TMS,isomer #1CCCCC/C=C\C/C=C\CCCCCCCC(=O)NCCO[Si](C)(C)C2698.3Semi standard non polar33892256
Linoleoyl ethanolamide,1TMS,isomer #1CCCCC/C=C\C/C=C\CCCCCCCC(=O)NCCO[Si](C)(C)C2602.1Standard non polar33892256
Linoleoyl ethanolamide,1TMS,isomer #1CCCCC/C=C\C/C=C\CCCCCCCC(=O)NCCO[Si](C)(C)C2974.0Standard polar33892256
Linoleoyl ethanolamide,1TMS,isomer #2CCCCC/C=C\C/C=C\CCCCCCCC(=O)N(CCO)[Si](C)(C)C2653.3Semi standard non polar33892256
Linoleoyl ethanolamide,1TMS,isomer #2CCCCC/C=C\C/C=C\CCCCCCCC(=O)N(CCO)[Si](C)(C)C2596.7Standard non polar33892256
Linoleoyl ethanolamide,1TMS,isomer #2CCCCC/C=C\C/C=C\CCCCCCCC(=O)N(CCO)[Si](C)(C)C3046.2Standard polar33892256
Linoleoyl ethanolamide,2TMS,isomer #1CCCCC/C=C\C/C=C\CCCCCCCC(=O)N(CCO[Si](C)(C)C)[Si](C)(C)C2690.3Semi standard non polar33892256
Linoleoyl ethanolamide,2TMS,isomer #1CCCCC/C=C\C/C=C\CCCCCCCC(=O)N(CCO[Si](C)(C)C)[Si](C)(C)C2738.0Standard non polar33892256
Linoleoyl ethanolamide,2TMS,isomer #1CCCCC/C=C\C/C=C\CCCCCCCC(=O)N(CCO[Si](C)(C)C)[Si](C)(C)C2781.4Standard polar33892256
Linoleoyl ethanolamide,1TBDMS,isomer #1CCCCC/C=C\C/C=C\CCCCCCCC(=O)NCCO[Si](C)(C)C(C)(C)C2929.7Semi standard non polar33892256
Linoleoyl ethanolamide,1TBDMS,isomer #1CCCCC/C=C\C/C=C\CCCCCCCC(=O)NCCO[Si](C)(C)C(C)(C)C2783.9Standard non polar33892256
Linoleoyl ethanolamide,1TBDMS,isomer #1CCCCC/C=C\C/C=C\CCCCCCCC(=O)NCCO[Si](C)(C)C(C)(C)C3005.2Standard polar33892256
Linoleoyl ethanolamide,1TBDMS,isomer #2CCCCC/C=C\C/C=C\CCCCCCCC(=O)N(CCO)[Si](C)(C)C(C)(C)C2871.2Semi standard non polar33892256
Linoleoyl ethanolamide,1TBDMS,isomer #2CCCCC/C=C\C/C=C\CCCCCCCC(=O)N(CCO)[Si](C)(C)C(C)(C)C2801.7Standard non polar33892256
Linoleoyl ethanolamide,1TBDMS,isomer #2CCCCC/C=C\C/C=C\CCCCCCCC(=O)N(CCO)[Si](C)(C)C(C)(C)C3068.3Standard polar33892256
Linoleoyl ethanolamide,2TBDMS,isomer #1CCCCC/C=C\C/C=C\CCCCCCCC(=O)N(CCO[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3165.2Semi standard non polar33892256
Linoleoyl ethanolamide,2TBDMS,isomer #1CCCCC/C=C\C/C=C\CCCCCCCC(=O)N(CCO[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3072.8Standard non polar33892256
Linoleoyl ethanolamide,2TBDMS,isomer #1CCCCC/C=C\C/C=C\CCCCCCCC(=O)N(CCO[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2879.9Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Linoleoyl ethanolamide GC-MS (Non-derivatized) - 70eV, Positivesplash10-0jbd-6980000000-296b477e994954e1473b2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Linoleoyl ethanolamide GC-MS (1 TMS) - 70eV, Positivesplash10-00di-9543000000-ffd6c325474236c1ad722017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Linoleoyl ethanolamide 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 - Linoleoyl ethanolamide 10V, Positive-QTOFsplash10-0229-6149000000-bb2fbbe45488da8f67b42017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Linoleoyl ethanolamide 20V, Positive-QTOFsplash10-03dl-9120000000-186b72964c13d07734a12017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Linoleoyl ethanolamide 40V, Positive-QTOFsplash10-03dl-9310000000-74ec109576a7e198699a2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Linoleoyl ethanolamide 10V, Negative-QTOFsplash10-00di-0029000000-cbc91ff6d8043670d9ba2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Linoleoyl ethanolamide 20V, Negative-QTOFsplash10-0h93-8079000000-a00a0ae3a1220d2215772017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Linoleoyl ethanolamide 40V, Negative-QTOFsplash10-0006-9010000000-2aa2259713b6e2b195322017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Linoleoyl ethanolamide 10V, Negative-QTOFsplash10-00di-0009000000-136b1b8ae59ab6324a702021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Linoleoyl ethanolamide 20V, Negative-QTOFsplash10-00di-5139000000-5a2a20a7ee6a618f57982021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Linoleoyl ethanolamide 40V, Negative-QTOFsplash10-06r6-9010000000-f671867a64400c3cd77c2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Linoleoyl ethanolamide 10V, Positive-QTOFsplash10-0229-9117000000-85c2fb6d17d62e45e2992021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Linoleoyl ethanolamide 20V, Positive-QTOFsplash10-03dl-9000000000-b5bb3da43d166e8e9d052021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Linoleoyl ethanolamide 40V, Positive-QTOFsplash10-07bf-9000000000-49357c837f95951f66152021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
BloodDetected and Quantified13.7 +/- 6.5 uMAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB028893
KNApSAcK IDNot Available
Chemspider ID4446566
KEGG Compound IDNot Available
BioCyc IDCPD6666-4
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5283446
PDB IDNot Available
ChEBI ID64032
Food Biomarker OntologyNot Available
VMH IDLINETH
MarkerDB IDNot Available
Good Scents IDrw1301201
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available