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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2010-05-20 13:47:29 UTC
Update Date2022-03-07 02:51:34 UTC
HMDB IDHMDB0013630
Secondary Accession Numbers
  • HMDB13630
Metabolite Identification
Common Name20-HETE ethanolamide
Description20-HETE ethanolamide 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 has been attributed a variety of biological activities, including neurotransmission, membrane protection, and immunomodulation in animals. N-Oleoylethanolamine is an inhibitor of the sphingolipid signalling 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?1582753138
Synonyms
ValueSource
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
Chemical FormulaC22H37NO3
Average Molecular Weight363.5341
Monoisotopic Molecular Weight363.277344055
IUPAC Name(5Z,8Z,11Z,14Z)-20-hydroxy-N-(2-hydroxyethyl)icosa-5,8,11,14-tetraenamide
Traditional Name20-hete-EA
CAS Registry Number942069-11-6
SMILES
OCCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(=O)NCCO
InChI Identifier
InChI=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
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 Solubility0.0028 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+197.20731661259
DarkChem[M-H]-203.00131661259
DeepCCS[M+H]+193.86730932474
DeepCCS[M-H]-191.50930932474
DeepCCS[M-2H]-224.64930932474
DeepCCS[M+Na]+200.05630932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
20-HETE ethanolamideOCCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(=O)NCCO3642.7Standard polar33892256
20-HETE ethanolamideOCCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(=O)NCCO2512.6Standard non polar33892256
20-HETE ethanolamideOCCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(=O)NCCO3136.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
20-HETE ethanolamide,1TMS,isomer #1C[Si](C)(C)OCCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)NCCO3172.1Semi standard non polar33892256
20-HETE ethanolamide,1TMS,isomer #2C[Si](C)(C)OCCNC(=O)CCC/C=C\C/C=C\C/C=C\C/C=C\CCCCCO3141.3Semi standard non polar33892256
20-HETE ethanolamide,1TMS,isomer #3C[Si](C)(C)N(CCO)C(=O)CCC/C=C\C/C=C\C/C=C\C/C=C\CCCCCO3060.8Semi standard non polar33892256
20-HETE ethanolamide,2TMS,isomer #1C[Si](C)(C)OCCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)NCCO[Si](C)(C)C3131.4Semi standard non polar33892256
20-HETE ethanolamide,2TMS,isomer #2C[Si](C)(C)OCCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)N(CCO)[Si](C)(C)C3097.8Semi standard non polar33892256
20-HETE ethanolamide,2TMS,isomer #3C[Si](C)(C)OCCN(C(=O)CCC/C=C\C/C=C\C/C=C\C/C=C\CCCCCO)[Si](C)(C)C3107.1Semi standard non polar33892256
20-HETE ethanolamide,3TMS,isomer #1C[Si](C)(C)OCCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)N(CCO[Si](C)(C)C)[Si](C)(C)C3115.6Semi standard non polar33892256
20-HETE ethanolamide,3TMS,isomer #1C[Si](C)(C)OCCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)N(CCO[Si](C)(C)C)[Si](C)(C)C3157.7Standard non polar33892256
20-HETE ethanolamide,3TMS,isomer #1C[Si](C)(C)OCCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)N(CCO[Si](C)(C)C)[Si](C)(C)C3028.3Standard polar33892256
20-HETE ethanolamide,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)NCCO3427.1Semi standard non polar33892256
20-HETE ethanolamide,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OCCNC(=O)CCC/C=C\C/C=C\C/C=C\C/C=C\CCCCCO3378.9Semi standard non polar33892256
20-HETE ethanolamide,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)N(CCO)C(=O)CCC/C=C\C/C=C\C/C=C\C/C=C\CCCCCO3301.1Semi standard non polar33892256
20-HETE ethanolamide,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)NCCO[Si](C)(C)C(C)(C)C3648.3Semi standard non polar33892256
20-HETE ethanolamide,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OCCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)N(CCO)[Si](C)(C)C(C)(C)C3568.0Semi standard non polar33892256
20-HETE ethanolamide,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OCCN(C(=O)CCC/C=C\C/C=C\C/C=C\C/C=C\CCCCCO)[Si](C)(C)C(C)(C)C3583.0Semi standard non polar33892256
20-HETE ethanolamide,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)N(CCO[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3863.0Semi standard non polar33892256
20-HETE ethanolamide,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)N(CCO[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3660.0Standard non polar33892256
20-HETE ethanolamide,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)N(CCO[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3149.7Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 20-HETE ethanolamide GC-MS (Non-derivatized) - 70eV, Positivesplash10-0j59-3589000000-3b2241d486c86688ef752017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 20-HETE ethanolamide GC-MS (2 TMS) - 70eV, Positivesplash10-0fdo-5439700000-2ce10d8e6ec266bf74972017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 20-HETE 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 - 20-HETE ethanolamide 10V, Positive-QTOFsplash10-03dj-3019000000-f2029ffb36e80f0831fa2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20-HETE ethanolamide 20V, Positive-QTOFsplash10-03dl-9023000000-b8b72230e0c2ee44dd702017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20-HETE ethanolamide 40V, Positive-QTOFsplash10-03dl-9131000000-46f2377e1f133b01723b2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20-HETE ethanolamide 10V, Negative-QTOFsplash10-03di-0009000000-f110e36f00b5948518052017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20-HETE ethanolamide 20V, Negative-QTOFsplash10-03dl-3009000000-83198bcf34c23d1f14af2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20-HETE ethanolamide 40V, Negative-QTOFsplash10-0006-9011000000-a8fbb4764172356595f92017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20-HETE ethanolamide 10V, Negative-QTOFsplash10-03di-0009000000-9e3358e490a06a8fff0c2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20-HETE ethanolamide 20V, Negative-QTOFsplash10-03di-3119000000-5a324625cccf8671a86f2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20-HETE ethanolamide 40V, Negative-QTOFsplash10-0006-9003000000-97c2fbd008005d7412432021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20-HETE ethanolamide 10V, Positive-QTOFsplash10-03di-7219000000-ae8a82a0373146ed1cda2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20-HETE ethanolamide 20V, Positive-QTOFsplash10-03dl-9001000000-0044622ae985419b24092021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20-HETE ethanolamide 40V, Positive-QTOFsplash10-03di-9300000000-46979c19002f897fe2ed2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.0208 +/- 0.013 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 IDFDB029607
KNApSAcK IDNot Available
Chemspider ID21467685
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound35027640
PDB IDNot Available
ChEBI ID136992
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 ]