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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2011-07-11 14:50:38 UTC
Update Date2022-03-07 02:51:34 UTC
HMDB IDHMDB0013658
Secondary Accession Numbers
  • HMDB13658
Metabolite Identification
Common NameDocosahexaenoyl Ethanolamide
DescriptionDocosahexaenoic Acid (DHA) is an essential fatty acid and the most abundant ω-3 fatty acid in neural tissues, especially in the retina and brain. Docosahexaenoyl ethanolamide (DHEA) is the ethanolamine amide of DHA that has been detected in both brain and retina at concentrations similar to those for arachidonoyl ethanolamide (AEA).1,2 A 9.5 fold increase of DHEA was observed in brain lipid extracts from piglets fed a diet supplemented with DHA compared to a control diet without DHA.3 DHEA binds to the rat brain CB1 receptor with a Ki of 324 nM, which is approximately 10-fold higher than the Ki for AEA.4 DHEA inhibits shaker-related voltage-gated potassium channels in brain slightly better than AEA, with an IC50 of 1.5 ¬µM.
Structure
Data?1582753141
Synonyms
ValueSource
Anandamide (22:6, N-3)ChEBI
N-(4Z,7Z,10Z,13Z,16Z,19Z)-Docosahexaenoyl ethanolamineChEBI
N-(4Z,7Z,10Z,13Z,16Z,19Z-Docosahexaenoyl)-ethanolamineChEBI
N-cis-4,7,10,13,16,19-DocosahexanoylethanolamineChEBI
DHEAHMDB
N-DocosahexaenoylethanolamineHMDB
SynaptamideHMDB
Chemical FormulaC24H37NO2
Average Molecular Weight371.5561
Monoisotopic Molecular Weight371.282429433
IUPAC Name(4Z,7Z,10Z,13Z,16Z,19Z)-N-(2-hydroxyethyl)docosa-4,7,10,13,16,19-hexaenamide
Traditional Name(4Z,7Z,10Z,13Z,16Z,19Z)-N-(2-hydroxyethyl)docosa-4,7,10,13,16,19-hexaenamide
CAS Registry Number162758-94-3
SMILES
CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCC(=O)NCCO
InChI Identifier
InChI=1S/C24H37NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-24(27)25-22-23-26/h3-4,6-7,9-10,12-13,15-16,18-19,26H,2,5,8,11,14,17,20-23H2,1H3,(H,25,27)/b4-3-,7-6-,10-9-,13-12-,16-15-,19-18-
InChI KeyGEEHOLRSGZPBSM-KUBAVDMBSA-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
Physiological effectNot Available
Disposition
Process
Role
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 Solubility0.00059 g/LALOGPS
logP6.17ALOGPS
logP5.48ChemAxon
logS-5.8ALOGPS
pKa (Strongest Acidic)15.45ChemAxon
pKa (Strongest Basic)-0.48ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area49.33 ŲChemAxon
Rotatable Bond Count16ChemAxon
Refractivity124.4 m³·mol⁻¹ChemAxon
Polarizability44.14 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]+202.67631661259
DarkChem[M-H]-199.30931661259
DeepCCS[M+H]+192.73430932474
DeepCCS[M-H]-190.37630932474
DeepCCS[M-2H]-224.50830932474
DeepCCS[M+Na]+199.73530932474
AllCCS[M+H]+199.932859911
AllCCS[M+H-H2O]+197.432859911
AllCCS[M+NH4]+202.332859911
AllCCS[M+Na]+202.932859911
AllCCS[M-H]-196.932859911
AllCCS[M+Na-2H]-199.432859911
AllCCS[M+HCOO]-202.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Docosahexaenoyl EthanolamideCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCC(=O)NCCO3774.8Standard polar33892256
Docosahexaenoyl EthanolamideCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCC(=O)NCCO2693.2Standard non polar33892256
Docosahexaenoyl EthanolamideCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCC(=O)NCCO3038.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Docosahexaenoyl Ethanolamide,1TMS,isomer #1CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCC(=O)NCCO[Si](C)(C)C3061.3Semi standard non polar33892256
Docosahexaenoyl Ethanolamide,1TMS,isomer #2CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCC(=O)N(CCO)[Si](C)(C)C2975.2Semi standard non polar33892256
Docosahexaenoyl Ethanolamide,2TMS,isomer #1CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCC(=O)N(CCO[Si](C)(C)C)[Si](C)(C)C3020.9Semi standard non polar33892256
Docosahexaenoyl Ethanolamide,2TMS,isomer #1CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCC(=O)N(CCO[Si](C)(C)C)[Si](C)(C)C3082.9Standard non polar33892256
Docosahexaenoyl Ethanolamide,2TMS,isomer #1CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCC(=O)N(CCO[Si](C)(C)C)[Si](C)(C)C2862.7Standard polar33892256
Docosahexaenoyl Ethanolamide,1TBDMS,isomer #1CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCC(=O)NCCO[Si](C)(C)C(C)(C)C3302.6Semi standard non polar33892256
Docosahexaenoyl Ethanolamide,1TBDMS,isomer #2CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCC(=O)N(CCO)[Si](C)(C)C(C)(C)C3255.3Semi standard non polar33892256
Docosahexaenoyl Ethanolamide,2TBDMS,isomer #1CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCC(=O)N(CCO[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3524.8Semi standard non polar33892256
Docosahexaenoyl Ethanolamide,2TBDMS,isomer #1CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCC(=O)N(CCO[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3455.1Standard non polar33892256
Docosahexaenoyl Ethanolamide,2TBDMS,isomer #1CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCC(=O)N(CCO[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2936.6Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Docosahexaenoyl Ethanolamide GC-MS (Non-derivatized) - 70eV, Positivesplash10-01pn-5689000000-9b4cf8006243e895d7fd2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Docosahexaenoyl Ethanolamide GC-MS (1 TMS) - 70eV, Positivesplash10-0229-9252500000-4110b89f2ab73a72a7762017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Docosahexaenoyl Ethanolamide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Docosahexaenoyl 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 - Docosahexaenoyl Ethanolamide 40V, Positive-QTOFsplash10-004l-9300000000-755a232bf686c9d61dfb2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Docosahexaenoyl Ethanolamide 20V, Positive-QTOFsplash10-00di-5963000000-a14e32bf4384a5ec6ab42021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Docosahexaenoyl Ethanolamide 10V, Positive-QTOFsplash10-00di-0139000000-cbd16ee9ab14480e22582021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Docosahexaenoyl Ethanolamide 40V, Positive-QTOFsplash10-004l-9300000000-0f4562ef3f5b1dc548982021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Docosahexaenoyl Ethanolamide 10V, Positive-QTOFsplash10-03k9-4019000000-b2b242bda3ce38e12aef2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Docosahexaenoyl Ethanolamide 20V, Positive-QTOFsplash10-03dl-9122000000-94df13a6db155fe1a2682017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Docosahexaenoyl Ethanolamide 40V, Positive-QTOFsplash10-03di-9131000000-501bb548fdce0075c37c2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Docosahexaenoyl Ethanolamide 10V, Negative-QTOFsplash10-00di-0009000000-741bef7b3dd5fb7030a02017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Docosahexaenoyl Ethanolamide 20V, Negative-QTOFsplash10-0h93-5009000000-b38e328eb1895d2389d42017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Docosahexaenoyl Ethanolamide 40V, Negative-QTOFsplash10-0006-9011000000-bf3dda5617b0256af5342017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Docosahexaenoyl Ethanolamide 10V, Positive-QTOFsplash10-0229-8219000000-ba8b3f4b94a4307def3a2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Docosahexaenoyl Ethanolamide 20V, Positive-QTOFsplash10-03dl-9000000000-ba6d821d8c695f4fc8472021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Docosahexaenoyl Ethanolamide 40V, Positive-QTOFsplash10-03di-9200000000-395426e731c4a00622ed2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Docosahexaenoyl Ethanolamide 10V, Negative-QTOFsplash10-00di-0009000000-ae9aa8ca13d13c461e972021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Docosahexaenoyl Ethanolamide 20V, Negative-QTOFsplash10-00di-5119000000-2c2db26f6fcb310f1f262021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Docosahexaenoyl Ethanolamide 40V, Negative-QTOFsplash10-0596-9002000000-8d2b9949220ff1f090c52021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB029628
KNApSAcK IDNot Available
Chemspider ID4446571
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5283451
PDB IDNot Available
ChEBI ID85252
Food Biomarker OntologyNot Available
VMH IDDOCOHXETH
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available