Showing metabocard for CE(20:3) (BMDB0006736)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 23:25:24 UTC
Update Date2020-04-22 15:18:24 UTC
BMDB IDBMDB0006736
Secondary Accession Numbers
  • BMDB06736
Metabolite Identification
Common NameCE(20:3)
DescriptionCE(20:3(8Z,11Z,14Z)) 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(20:3(8Z,11Z,14Z)) may also accumulate in hereditary hypercholesterolemia, an inborn error of metabolism.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
CE(20:3)Lipid Annotator, HMDB
CE(20:3/0:0)Lipid Annotator, HMDB
Cholesterol Ester(20:3/0:0)Lipid Annotator, HMDB
cholesterol 1-(8Z,11Z,14Z-eicosatrienoic acid)Lipid Annotator, HMDB
cholesteryl 1-homo-g-linolenoateLipid Annotator, HMDB
Cholesterol Ester(20:3)Lipid Annotator, HMDB
cholesterol 1-homo-g-linolenoateLipid Annotator, HMDB
cholesterol 1-homo-g-linolenoic acidLipid Annotator, HMDB
cholesterol 1-(8Z,11Z,14Z-eicosatrienoate)Lipid Annotator, HMDB
cholesteryl 1-homo-g-linolenoic acidLipid Annotator, HMDB
cholesteryl 1-(8Z,11Z,14Z-eicosatrienoic acid)Lipid Annotator, HMDB
20:3(8Z,11Z,14Z) cholesterol esterLipid Annotator, HMDB
cholesteryl 1-(8Z,11Z,14Z-eicosatrienoate)Lipid Annotator, HMDB
1-homo-g-linolenoyl-cholesterolLipid Annotator, HMDB
1-(8Z,11Z,14Z-eicosatrienoyl)-cholesterolLipid Annotator, HMDB
CE(20:3(8Z,11Z,14Z))Lipid Annotator
20:3 Cholesterol esterHMDB
Cholest-5-en-3beta-yl (8Z,11Z,14Z-eicosatrienoateHMDB
Cholest-5-en-3beta-yl (8Z,11Z,14Z-eicosatrienoate)HMDB
Cholest-5-en-3beta-yl (8Z,11Z,14Z-eicosatrienoic acidHMDB
Cholesteryl eicosatrienoateHMDB
Cholesteryl eicosatrienoic acidHMDB
(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 (8Z,11Z,14Z)-icosa-8,11,14-trienoic acidGenerator
Chemical FormulaC47H78O2
Average Molecular Weight675.121
Monoisotopic Molecular Weight674.60018174
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 (8Z,11Z,14Z)-icosa-8,11,14-trienoate
Traditional 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 (8Z,11Z,14Z)-icosa-8,11,14-trienoate
CAS Registry Number7274-08-0
SMILES
CCCCC\C=C/C\C=C/C\C=C/CCCCCCC(=O)O[C@H]1CC[C@@]2(C)C(=CCC3C4CCC([C@H](C)CCCC(C)C)[C@@]4(C)CCC23)C1
InChI Identifier
InChI=1S/C47H78O2/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/h11-12,14-15,17-18,28,37-38,40-44H,7-10,13,16,19-27,29-36H2,1-6H3/b12-11-,15-14-,18-17-/t38-,40+,41?,42?,43?,44?,46+,47-/m1/s1
InChI KeyMLPRJPSMAFZPLA-PJSAOELNSA-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
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP10.52ALOGPS
logP14.73ChemAxon
logS-8.1ALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count22ChemAxon
Refractivity215.96 m³·mol⁻¹ChemAxon
Polarizability88.92 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004r-1054019000-6d4523a79502abfafda7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-5189022000-be6e9cfa5db1acc6bd3cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0cdj-5379002000-8597a576901e146de78cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00dr-0015009000-f1056d88f463657c1679View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0029002000-38ebf00723c57b23d200View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00ku-2029000000-3798fabcce628f95cd48View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0001009000-95aec06de375210637b1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0007019000-963018ed96675dfb58fbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4r-9224317000-bf67e803ae38ee606866View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00or-6129048000-a9b91490b027938241a0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-069r-9110011000-08b5fb6a76f72e86844fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-069u-9100010000-d72dcbcb7c04123af336View in MoNA
MSMass Spectrum (Electron Ionization)Not AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0006736
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB024050
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC02530
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53477892
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available