Showing metabocard for 18:1 Cholesteryl ester (BMDB0062600)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2018-08-29 17:08:33 UTC
Update Date2020-06-04 19:58:08 UTC
BMDB IDBMDB0062600
Secondary Accession Numbers
  • BMDB62600
Metabolite Identification
Common Name18:1 Cholesteryl ester
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
(3beta)-Cholest-5-en-3-ol, (Z)-9-octadecenoateChEBI
18:1 Cholesteryl esterChEBI
CE(18:1)ChEBI
Cholest-5-en-3-beta-yl oleateChEBI
Cholest-5-en-3-yl (9Z)-9-octadecenoateChEBI
Cholesteryl (9Z-octadecenoate)ChEBI
Cholesteryl cis-9-octadecenoateChEBI
OleoylcholesterolChEBI
(3b)-Cholest-5-en-3-ol, (Z)-9-octadecenoateGenerator
(3b)-Cholest-5-en-3-ol, (Z)-9-octadecenoic acidGenerator
(3beta)-Cholest-5-en-3-ol, (Z)-9-octadecenoic acidGenerator
(3Β)-cholest-5-en-3-ol, (Z)-9-octadecenoateGenerator
(3Β)-cholest-5-en-3-ol, (Z)-9-octadecenoic acidGenerator
Cholest-5-en-3-b-yl oleateGenerator
Cholest-5-en-3-b-yl oleic acidGenerator
Cholest-5-en-3-beta-yl oleic acidGenerator
Cholest-5-en-3-β-yl oleateGenerator
Cholest-5-en-3-β-yl oleic acidGenerator
Cholest-5-en-3-yl (9Z)-9-octadecenoic acidGenerator
Cholesteryl (9Z-octadecenoic acid)Generator
Cholesteryl cis-9-octadecenoic acidGenerator
1-Oleoyl-cholesterolHMDB
18:1(9Z) Cholesterol esterHMDB
3beta-Hydroxy-5-cholestene 3-oleateHMDB
5-Cholesten-3b-ol 3-oleateHMDB
CE(18:1/0:0)HMDB
CE(18:1n9/0:0)HMDB
CE(18:1W9/0:0)HMDB
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 oleateHMDB, MeSH
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
Cholesteryl oleate, (e)-isomerMeSH
Cholesterol oleateMeSH
CE(18:1(9Z))ChEBI
Cholesteryl oleic acidGenerator
Chemical FormulaC45H78O2
Average Molecular Weight651.0996
Monoisotopic Molecular Weight650.60018174
IUPAC Name(1S,2R,5S,10S,11S,14R,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(1S,2R,5S,10S,11S,14R,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
[H]\C(CCCCCCCC)=C(/[H])CCCCCCCC(=O)O[C@@]1([H])CC[C@@]2(C)C(C1)=CC[C@@]1([H])[C@]3([H])CC[C@]([H])([C@]([H])(C)CCCC(C)C)[C@@]3(C)CC[C@]21[H]
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-RMUVNZEASA-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 Descriptors
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
logP10.68ALOGPS
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
Polarizability86.81 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
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0udi-0000009000-21a92605782172dbfd15View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0udi-0000009000-06ae92b73dd60f6a7e36View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-002o-0800980000-fc08d63d7e4e8b45f921View 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, 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
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Milk
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
MilkDetected and Quantified7.6 +/- 0.1 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified8.5 +/- 0.2 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified8.82 +/- 0.03 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified4.1 +/- 0.1 uMNot SpecifiedNot Specified
Normal		 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 IDC14641
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5283632
PDB IDNot Available
ChEBI ID46898
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. A. Foroutan et al. (2019). A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation). Journal of Agricultural and Food Chemistry.