Showing metabocard for CE(16:1(9Z)) (BMDB0000658)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:34:26 UTC
Update Date2020-06-04 19:29:20 UTC
BMDB IDBMDB0000658
Secondary Accession Numbers
  • BMDB00658
Metabolite Identification
Common NameCE(16:1(9Z))
DescriptionCE(16:1(9Z)) 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(16:1(9Z)) may also accumulate in hereditary hypercholesterolemia, an inborn error of metabolism.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(Z)-Cholesterol 9-hexadecenoateHMDB
(Z)-Cholesterol 9-hexadecenoic acidHMDB
1-Palmitoleoyl-cholesterolHMDB
16:1(9Z) Cholesterol esterHMDB
CE(16:1)HMDB
CE(16:1/0:0)HMDB
CE(16:1n7/0:0)HMDB
CE(16:1W7/0:0)HMDB
Cholest-5-en-3beta-yl (9Z hexadecenoateHMDB
Cholest-5-en-3beta-yl (9Z hexadecenoate)HMDB
Cholest-5-en-3beta-yl (9Z hexadecenoic acidHMDB
Cholesterol 1-(9Z-hexadecenoateHMDB
Cholesterol 1-(9Z-hexadecenoate)HMDB
Cholesterol 1-(9Z-hexadecenoic acidHMDB
Cholesterol 1-(9Z-hexadecenoic acid)HMDB
Cholesterol 1-palmitoleoateHMDB
Cholesterol 1-palmitoleoic acidHMDB
Cholesterol ester(16:1)HMDB
Cholesterol ester(16:1/0:0)HMDB
Cholesterol ester(16:1n7/0:0)HMDB
Cholesterol ester(16:1W7/0:0)HMDB
Cholesterol palmitoleateHMDB
Cholesteryl 1-(9Z-hexadecenoateHMDB
Cholesteryl 1-(9Z-hexadecenoate)HMDB
Cholesteryl 1-(9Z-hexadecenoic acidHMDB
Cholesteryl 1-(9Z-hexadecenoic acid)HMDB
Cholesteryl 1-palmitoleoateHMDB
Cholesteryl 1-palmitoleoic acidHMDB
Cholesteryl cis-hexadecenoateHMDB
Cholesteryl cis-hexadecenoic acidHMDB
Cholesteryl palmitoleatHMDB
Cholesteryl palmitoleateHMDB
Cholesteryl palmitoleic acidHMDB
(2R,14R,15R)-2,15-Dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0,.0,]heptadec-7-en-5-yl (9Z)-hexadec-9-enoic acidGenerator
Chemical FormulaC43H74O2
Average Molecular Weight623.0465
Monoisotopic Molecular Weight622.568881612
IUPAC Name(2R,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-yl (9Z)-hexadec-9-enoate
Traditional Namecholesteryl palmitoleate
CAS Registry Number16711-66-3
SMILES
CCCCCC\C=C/CCCCCCCC(=O)OC1CC[C@@]2(C)C(=CCC3C4CC[C@H]([C@H](C)CCCC(C)C)[C@@]4(C)CCC23)C1
InChI Identifier
InChI=1S/C43H74O2/c1-7-8-9-10-11-12-13-14-15-16-17-18-19-23-41(44)45-36-28-30-42(5)35(32-36)24-25-37-39-27-26-38(34(4)22-20-21-33(2)3)43(39,6)31-29-40(37)42/h12-13,24,33-34,36-40H,7-11,14-23,25-32H2,1-6H3/b13-12-/t34-,36?,37?,38-,39?,40?,42+,43-/m1/s1
InChI KeyHODJWNWCVNUPAQ-FSAOOAOSSA-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
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
logP10.44ALOGPS
logP13.67ChemAxon
logS-8ALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count20ChemAxon
Refractivity195.32 m³·mol⁻¹ChemAxon
Polarizability82.89 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, Positivesplash10-0a4l-4529073000-025ba6e44b9eae49618dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00di-0000009000-a7e456f0a355d64105baView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00di-0101009000-2567065e6acdb75c7d42View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0a4i-4930000000-5906548ca9900baba4deView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00dr-1255039000-31eda8d2e0d85c9d0306View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05n0-5449030000-a600e4e0cfe381e9f7a7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-5719230000-9c5803bd30c50c2ab1fdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00dr-0024009000-69f58d56b9aab51b71eaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0049003000-e8baef11f1d1279c69acView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00ku-2029000000-940b494f7a9dcf0e372cView in MoNA
1D NMR1H NMR Spectrum (1D, 600 MHz, CDCl3, experimental)Not AvailableView in JSpectraViewer
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental)Not AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Ruminal Fluid
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Ruminal FluidDetected and Quantified1.7 +/- 1.21 uMNot SpecifiedNot SpecifiedNormal
    • Fozia Saleem, Sou...
 details
Ruminal FluidDetected and Quantified1.7 +/- 1.3 uMNot SpecifiedNot Specified
Normal
    • Fozia Saleem, Sou...
 details
Abnormal Concentrations
Not Available
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound22833543
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceWang, Stephen T.; Peter, Frank. Gas-liquid chromatographic determination of fatty acid composition of cholesteryl esters in human serum using silica Sep-Pak cartridges. Journal of Chromatography (1983), 276(2), 249-56.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available