Cervonoyl ethanolamide (CHEM041392)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-27 01:26:36 UTC
Update Date2016-11-09 01:22:28 UTC
Accession NumberCHEM041392
Identification
Common NameCervonoyl ethanolamide
ClassSmall Molecule
DescriptionCervonoyl 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).
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
8,11,14-EicosatrienoylethanolamideHMDB
DHEAHMDB
N-(8Z,11Z,14Z-Icosatrienoyl)-ethanolamideHMDB
2-Hydroxyethyl (7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoic acidGenerator
Chemical FormulaC24H36O3
Average Molecular Mass372.541 g/mol
Monoisotopic Mass372.266 g/mol
CAS Registry NumberNot Available
IUPAC Name2-hydroxyethyl (4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoate
Traditional Name2-hydroxyethyl (4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoate
SMILESCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCC(=O)OCCO
InChI IdentifierInChI=1S/C24H36O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-24(26)27-23-22-25/h3-4,6-7,9-10,12-13,15-16,18-19,25H,2,5,8,11,14,17,20-23H2,1H3/b4-3-,7-6-,10-9-,13-12-,16-15-,19-18-
InChI KeyCXWASNUDKUTFPQ-KUBAVDMBSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acid esters
Direct ParentFatty acid esters
Alternative Parents
Substituents
  • Fatty acid ester
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.00024 g/LALOGPS
logP6.39ALOGPS
logP6.21ChemAxon
logS-6.2ALOGPS
pKa (Strongest Acidic)15.1ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 ŲChemAxon
Rotatable Bond Count17ChemAxon
Refractivity122.45 m³·mol⁻¹ChemAxon
Polarizability43.58 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-01pk-8396000000-1d0ace2b11d6c40b1fc2Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0h90-9475100000-2b65ef5fc990f79bd551Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-022a-4029000000-3f41db329532c552a58bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01ot-9285000000-1bd3653b820ae596457aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-015a-6492000000-64839389b6d689bd9c4fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-05i0-1009000000-772e93af60e404792c14Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a6u-4019000000-9b3d7464ebad01b4522bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9023000000-4e78056ea7ac55147ea9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0229-3229000000-f7e676aef96eeef441ccSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03l1-9546000000-dcada1f4b00ac93a9a4fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05o3-7901000000-83db43f3646c8ea3ce65Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0adi-0009000000-ab994d80fe196d45ffd2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a6r-5009000000-c5255753e4ef1c3ee624Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05i1-8195000000-13c882cacb1117324af4Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0013627
FooDB IDFDB029604
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID30776716
ChEBI ID34488
PubChem Compound ID53245830
Kegg Compound IDC13828
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot 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.
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.
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.
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.
5. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
6. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10.
7. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20.
8. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.
9. The lipid handbook with CD-ROM