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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2010-05-20 12:52:41 UTC
Update Date2019-07-23 05:59:14 UTC
HMDB IDHMDB0013626
Secondary Accession Numbers
  • HMDB13626
Metabolite Identification
Common NameAdrenoyl ethanolamide
DescriptionAdrenoyl 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?1563861554
Synonyms
ValueSource
N-(7Z,10Z,13Z,16Z-Docosatetraenoyl)-ethanolamideKegg
7,10,13,16-DocosatetraenoylethanolamineHMDB
7,10,13,16-DocosatetraenylethanolamideHMDB
8,11,14-EicosatrienoylethanolamideHMDB
Adrenoyl-ethanolamineHMDB
DEAHMDB
Docosa-7,10,13,16-tetraenoateHMDB
Docosa-7,10,13,16-tetraenoic acidHMDB
Docosa-7,10,13,16-tetraenoic acid (2-hydroxy-ethyl)-amideHMDB
N-(8Z,11Z,14Z-Icosatrienoyl)-ethanolamideHMDB
7,10,13,16-DTEAMeSH
Chemical FormulaC24H41NO2
Average Molecular Weight375.5878
Monoisotopic Molecular Weight375.313729561
IUPAC Name(7Z,10Z,13Z,16Z)-N-(2-hydroxyethyl)docosa-7,10,13,16-tetraenamide
Traditional Namedocosatetraenoylethanolamide
CAS Registry Number150314-35-5
SMILES
CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCCCC(=O)NCCO
InChI Identifier
InChI=1S/C24H41NO2/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/h6-7,9-10,12-13,15-16,26H,2-5,8,11,14,17-23H2,1H3,(H,25,27)/b7-6-,10-9-,13-12-,16-15-
InChI KeyFMVHVRYFQIXOAF-DOFZRALJSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as n-acylethanolamines. These 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

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.00019 g/LALOGPS
logP6.58ALOGPS
logP6.2ChemAxon
logS-6.3ALOGPS
pKa (Strongest Acidic)15.46ChemAxon
pKa (Strongest Basic)-0.33ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area49.33 ŲChemAxon
Rotatable Bond Count18ChemAxon
Refractivity122.17 m³·mol⁻¹ChemAxon
Polarizability47.17 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-014l-8596000000-fb56397a219ca27323eeJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00yi-9263400000-08ff1e6d3a4de7602967JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01t9-4019000000-af6365155318609eed17JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dl-9122000000-8e28d155f14c7badafedJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-9130000000-e57644d2630bb1b3b060JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0009000000-7ec4d3341aea6c7e0b11JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-074l-5009000000-00b3c02e8e16ba5c1e65JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9011000000-d5cb6f4617816a6a0fb2JSpectraViewer | MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified1.63 +/- 0.78 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
FoodDB IDFDB029603
KNApSAcK IDNot Available
Chemspider ID4445444
KEGG Compound IDC13829
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5282273
PDB IDNot Available
ChEBI ID269625
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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 ]
  2. 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 ]
  3. 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 ]
  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 ]