Showing metabocard for CE(18:1(9Z)) (BMDB0000918)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:38:36 UTC
Update Date2020-06-04 19:55:34 UTC
BMDB IDBMDB0000918
Secondary Accession Numbers
  • BMDB00918
Metabolite Identification
Common NameCE(18:1(9Z))
DescriptionCE(18:1(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(18:1(9Z)) may also accumulate in hereditary hypercholesterolemia, an inborn error of metabolism.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-Oleoyl-cholesterolHMDB
18:1(9Z) Cholesterol esterHMDB
3beta-Hydroxy-5-cholestene 3-oleateHMDB
5-Cholesten-3b-ol 3-oleateHMDB
CE(18:1)HMDB
CE(18:1/0:0)HMDB
CE(18:1n9/0:0)HMDB
CE(18:1W9/0:0)HMDB
Cholest-5-en-3-beta-yl oleateHMDB
Cholest-5-en-3-ol (3b)-(Z)-9-octadecenoateHMDB
Cholest-5-en-3-ol (3b)-(Z)-9-octadecenoic acidHMDB
Cholest-5-en-3b-ylHMDB
Cholesterol 1-(9Z-octadecenoateHMDB
Cholesterol 1-(9Z-octadecenoate)HMDB
Cholesterol 1-(9Z-octadecenoic acidHMDB
Cholesterol 1-(9Z-octadecenoic acid)HMDB
Cholesterol 3beta-oleateHMDB
Cholesterol ester(18:1)HMDB
Cholesterol ester(18:1/0:0)HMDB
Cholesterol ester(18:1n9/0:0)HMDB
Cholesterol ester(18:1W9/0:0)HMDB
Cholesteroyl-oleateHMDB
Cholesteryl 1-oleoateHMDB
Cholesteryl 1-oleoic acidHMDB
Cholesteryl cis-9-octadecenoateHMDB
Cholesteryl cis-9-octadecenoic acidHMDB
Cholesteryl oleateHMDB
Cholesteryl oleate-9,10-3HHMDB
Cholesteryl oleate-9,10-t2HMDB
Cholesteryl oleic esterHMDB
Cholesteryl [9,10-3H]oleateHMDB
Cholesteryl-beta-D-glucosideHMDB
Cholesteryl-beta-delta-glucosideHMDB
Oleic acid cholesteryl esterHMDB
OleoylcholesterolHMDB
Cholesteryl 1-(9Z-octadecenoate)HMDB
Cholesterol 1-oleoic acidHMDB
Cholesteryl 1-(9Z-octadecenoic acid)HMDB
Cholesterol 1-oleoateHMDB
1-(9Z-Octadecenoyl)-cholesterolHMDB
CE(18:1(9Z))Lipid Annotator
Chemical FormulaC45H78O2
Average Molecular Weight651.117
Monoisotopic Molecular Weight650.600181752
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)-octadec-9-enoate
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)-octadec-9-enoate
CAS Registry Number303-43-5
SMILES
CCCCCCCC\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/C45H78O2/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/h14-15,26,35-36,38-42H,7-13,16-25,27-34H2,1-6H3/b15-14-/t36-,38+,39?,40?,41?,42?,44+,45-/m1/s1
InChI KeyRJECHNNFRHZQKU-DVPYOPPASA-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
  • Myelin sheath
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP10.68ALOGPS
logP14.56ChemAxon
logS-8ALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count22ChemAxon
Refractivity204.53 m³·mol⁻¹ChemAxon
Polarizability87.32 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, Positivesplash10-00ku-5359047000-b0786012be7d0cac7c83View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0024009000-dccc63058b1b8d7cddc9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0049003000-755458c70f1eed13712dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00ku-2029000000-170f3ca0c9bd97272276View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uxr-1165029000-1ce7930cf3150163fd8dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01bi-5379031000-e18668a49f8d8d48ee71View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0629-6369130000-9782f8bcc5e881bea861View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0gc0-4039026000-807a77313ffb119421bdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4l-9110000000-d78ed0ea6e721a187f92View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9100000000-4804d89b0b9e262fabb9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0020009000-d95a9dce4154675002c9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0013009000-ecd587e023698b4f55cdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0btj-8767697000-e635b5469ba14e38a163View in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Membrane
  • Myelin sheath
Biospecimen Locations
  • Adipose Tissue
  • Adrenal Cortex
  • Adrenal Gland
  • Epidermis
  • Fibroblasts
  • Intestine
  • Liver
  • Neuron
  • Platelet
  • Ruminal Fluid
  • Spleen
  • Testis
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Adipose TissueExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Adrenal CortexExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Adrenal GlandExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
EpidermisExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
FibroblastsExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
IntestineExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
LiverExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
NeuronExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
PlateletExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Ruminal FluidDetected and Quantified23.5 +/- 15.68 uMNot SpecifiedNot SpecifiedNormal
    • Fozia Saleem, Sou...
 details
Ruminal FluidDetected and Quantified23.5 +/- 15.7 uMNot SpecifiedNot Specified
Normal
    • Fozia Saleem, Sou...
 details
SpleenExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
TestisExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0000918
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022317
KNApSAcK IDNot Available
Chemspider ID26263151
KEGG Compound IDC14641
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5872
PubChem Compound50938266
PDB IDNot Available
ChEBI ID46898
References
Synthesis ReferenceSripada P K Synthesis of single- and double-13C-labeled cholesterol oleate. Chemistry and physics of lipids (1988), 48(1-2), 147-51.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available