Showing metabocard for CE(18:2(9Z,12Z)) (BMDB0000610)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:33:33 UTC
Update Date2020-06-04 19:55:32 UTC
BMDB IDBMDB0000610
Secondary Accession Numbers
  • BMDB00610
Metabolite Identification
Common NameCE(18:2(9Z,12Z))
DescriptionCE(18:2(9Z,12Z)) 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(18:2(9Z,12Z)) may also accumulate in hereditary hypercholesterolemia, an inborn error of metabolism.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Cholesterol ester(18:2)HMDB
Cholesteryl 1-linoleoic acidHMDB
Cholesterol ester(18:2/0:0)HMDB
Cholesterol 1-(9Z,12Z-octadecadienoate)HMDB
Cholesteryl 1-(9Z,12Z-octadecadienoate)HMDB
18:2(9Z,12Z) Cholesterol esterHMDB
Cholesteryl 1-linoleoateHMDB
1-Linoleoyl-cholesterolHMDB
Cholesterol 1-(9Z,12Z-octadecadienoic acid)HMDB
CE(18:2)HMDB
CE(18:2/0:0)HMDB
Cholesterol 1-linoleoateHMDB
Cholesteryl 1-(9Z,12Z-octadecadienoic acid)HMDB
1-(9Z,12Z-Octadecadienoyl)-cholesterolHMDB
Cholesterol 1-linoleoic acidHMDB
CE(18:2n6/0:0)HMDB
CE(18:2W6/0:0)HMDB
Cholest-5-en-3beta-yl (9Z,12Z-octadecadienoateHMDB
Cholest-5-en-3beta-yl (9Z,12Z-octadecadienoate)HMDB
Cholest-5-en-3beta-yl (9Z,12Z-octadecadienoic acidHMDB
Cholesterol 1-(9Z,12Z-octadecadienoateHMDB
Cholesterol 1-(9Z,12Z-octadecadienoic acidHMDB
Cholesterol ester(18:2n6/0:0)HMDB
Cholesterol ester(18:2W6/0:0)HMDB
Cholesteryl 1-(9Z,12Z-octadecadienoateHMDB
Cholesteryl 1-(9Z,12Z-octadecadienoic acidHMDB
CE(18:2(9Z,12Z))Lipid Annotator
Chemical FormulaC45H76O2
Average Molecular Weight649.101
Monoisotopic Molecular Weight648.584531687
IUPAC Name(2R,5S,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-yl (9Z,12Z)-octadeca-9,12-dienoate
Traditional Name(2R,5S,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-yl (9Z,12Z)-octadeca-9,12-dienoate
CAS Registry Number604-33-1
SMILES
CCCCC\C=C/C\C=C/CCCCCCCC(=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/C45H76O2/c1-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-25-43(46)47-38-30-32-44(5)37(34-38)26-27-39-41-29-28-40(36(4)24-22-23-35(2)3)45(41,6)33-31-42(39)44/h11-12,14-15,26,35-36,38-42H,7-10,13,16-25,27-34H2,1-6H3/b12-11-,15-14-/t36-,38+,39?,40?,41?,42?,44+,45-/m1/s1
InChI KeyNAACPBBQTFFYQB-XHDSEGDBSA-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
  • Octadecanoid
  • 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
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
logP10.5ALOGPS
logP14.2ChemAxon
logS-8ALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count21ChemAxon
Refractivity205.64 m³·mol⁻¹ChemAxon
Polarizability85.97 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-02cu-2249036000-982a939d936e4145f409View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0024009000-cce26a76d81022551064View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0049003000-279ae0d99e8b8a89b4eaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00ku-2029000000-286796af38311acd982dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-1055029000-278e2cdd4d844602dfe0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-02g9-5279041000-8c335b2ffc97bdef290bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0axr-5359120000-7e557cfcdd9040140e0bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-015a-7039035000-47b4fa82b20e214ae3a9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ar3-9110000000-4dd080a1ca6afce34307View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0693-9000000000-418b033dae70fbd95e3fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0010009000-a6b6ac51bf34d1af7171View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0014009000-ab709a37518dc30c3b84View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0bti-9534344000-4b4e1bca9ae4b53e7531View in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Ruminal Fluid
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Ruminal FluidDetected and Quantified15.1 +/- 7.3 uMNot SpecifiedNot SpecifiedNormal
    • Fozia Saleem, Sou...
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0000610
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022141
KNApSAcK IDNot Available
Chemspider ID4450205
KEGG Compound IDC15441
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5584
PubChem Compound131801653
PDB IDNot Available
ChEBI ID41509
References
Synthesis ReferenceLundberg, Bo; Pellas, Lars. Preparation and characterization of cholesteryl linoleate. Acta Academiae Aboensis, Series B: Mathematica et Physica (1973), 33(4), 4 pp.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available