Showing metabocard for CE(20:0) (LMDB00933)

IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-08-01 22:02:34 UTC
Update Date2016-08-02 20:40:55 UTC
LmdbLMDB00933
Secondary Accession NumbersNone
Metabolite Identification
Common NameCE(20:0)
DescriptionCE(20:0) belongs to the family of cholesteryl esters, whose structure is characetized by a cholesterol esterified at the 3-position with a fatty acid. A cholesteryl ester is an ester of cholesterol. Fatty acid esters of cholesterol constitute about two-thirds of the cholesterol in the plasma. Cholesterol is a sterol (a combination steroid and alcohol) and a lipid found in the cell membranes of all body tissues, and transported in the blood plasma of all animals. The accumulation of cholesterol esters in the arterial intima (the innermost layer of an artery, in direct contact with the flowing blood) is a characteristic feature of atherosclerosis. Atherosclerosis is a disease affecting arterial blood vessels. It is a chronic inflammatory response in the walls of arteries, in large part to the deposition of lipoproteins (plasma proteins that carry cholesterol and triglycerides). CE(20:0) may also accumulate in hereditary hypercholesterolemia, an inborn error of metabolism.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-Arachidonyl-cholesterolHMDB
20:0 Cholesterol esterHMDB
CE(20:0/0:0)HMDB
Cholest-5-en-3b-yl eicosanoateHMDB
Cholest-5-en-3b-yl eicosanoic acidHMDB
Cholesterol 1-arachidonylHMDB
Cholesterol 1-eicosanoateHMDB
Cholesterol 1-eicosanoic acidHMDB
Cholesterol arachidateHMDB
Cholesterol ester(20:0)HMDB
Cholesterol ester(20:0/0:0)HMDB
Cholesteryl 1-arachidonylHMDB
Cholesteryl 1-eicosanoateHMDB
Cholesteryl 1-eicosanoic acidHMDB
Cholesteryl arachidateHMDB
Cholesteryl eicosanoateHMDB
Cholesteryl eicosanoic acidHMDB
EicosanoateHMDB
Eicosanoic acidHMDB
Eicosanoic acidcholesteryl esterHMDB
1-Eicosanoyl-cholesterolHMDB
(2R,5S,15R)-2,15-Dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-yl icosanoic acidHMDB
CE(20:0)Lipid Annotator
Chemical FormulaC47H84O2
Average Molecular Weight681.1687
Monoisotopic Molecular Weight680.647131932
IUPAC Name(2R,5S,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-yl icosanoate
Traditional Namecholesteryl arachidate
CAS Registry NumberNot Available
SMILES
CCCCCCCCCCCCCCCCCCCC(=O)O[C@H]1CC[C@]2(C)C3CC[C@]4(C)C(CCC4C3CC=C2C1)[C@H](C)CCCC(C)C
InChI Identifier
InChI=1S/C47H84O2/c1-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-27-45(48)49-40-32-34-46(5)39(36-40)28-29-41-43-31-30-42(38(4)26-24-25-37(2)3)47(43,6)35-33-44(41)46/h28,37-38,40-44H,7-27,29-36H2,1-6H3/t38-,40+,41?,42?,43?,44?,46+,47-/m1/s1
InChI KeySUOVMGLZSOAHJY-YEYBIBAWSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as cholesteryl esters. Cholesteryl esters are compounds containing an esterified cholestane moiety.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassSteroid esters
Direct ParentCholesteryl esters
Alternative Parents
Substituents
  • Cholesteryl ester
  • Cholesterol
  • Cholestane-skeleton
  • Delta-5-steroid
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
StatusDetected and Quantified
OriginNot Available
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP10.96ALOGPS
logP15.81ChemAxon
logS-8ALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count25ChemAxon
Refractivity212.61 m³·mol⁻¹ChemAxon
Polarizability92.31 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-014i-5138049000-c9f36f37e6192bce0619Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-1154019000-a5da64f5bf6ecdafcb8aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0671-4269012000-33c1817aca87bb15d9cfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0adi-5349033000-be9ba11b794ba37822adSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0015009000-2e4e8d50b93c6e8fdf2fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0029002000-d2277e4a0dbc482fccd4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014u-2019000000-34613e30dc1d3899d254Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0002009000-d015082d3ba53606986bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0004009000-dfd17f5b1b8ec18e519dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-08p0-3223429000-cf3cab58637e780cf0c5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00lr-5039016000-c6e19a6e97c251a9dbcdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052f-9031001000-e27b3d2a755211aaafb0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9310000000-28dbfdb34daa34f651ddSpectrum
Biological Properties
Cellular LocationsNot Available
Biofluid Locations and Tissue Locations
  • Ruminal Fluid
Concentrations
BiofluidStatusValueConditionSpeciesReferenceDetails
Ruminal FluidDetected and Quantified4.4 +/- 2.4 uMNot AvailableBovine
    • Saleem F, Bouatra...
 details
DrugBank IDNot Available
HMDB IDHMDB0006740
FooDB IDFDB024053
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider IDNot Available
ChEBI ID88763
PubChem Compound ID53477894
Kegg Compound IDC02530
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available