Showing metabocard for 18:1 Cholesteryl ester (BMDB0062600)

IdentificationTaxonomyPhysical propertiesSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2018-08-29 17:08:33 UTC
Update Date2020-06-04 19:58:08 UTC
MCDB ID BMDB0062600
Secondary Accession Numbers
  • BMDB62600
Metabolite Identification
Common Name18:1 Cholesteryl ester
DescriptionCe(18:1(9Z)), also known as ce(18:1) or oleoylcholesterol, belongs to the class of organic compounds known as cholesteryl esters. Cholesteryl esters are compounds containing an esterified cholestane moiety. Thus, ce(18:1(9Z)) is considered to be a sterol lipid molecule. Ce(18:1(9Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
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
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
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00ku-5359047000-b0786012be7d0cac7c832017-09-01View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0udi-0000009000-21a92605782172dbfd152012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0udi-0000009000-06ae92b73dd60f6a7e362012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-002o-0800980000-fc08d63d7e4e8b45f9212012-07-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uxr-1165029000-1ce7930cf3150163fd8d2017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01bi-5379031000-e18668a49f8d8d48ee712017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0629-6369130000-9782f8bcc5e881bea8612017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0024009000-dccc63058b1b8d7cddc92017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0049003000-755458c70f1eed13712d2017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00ku-2029000000-170f3ca0c9bd972722762017-09-01View Spectrum
Concentrations
StatusValueReferenceDetails
Detected and Quantified7.6 +/- 0.1 uM details
Detected and Quantified8.5 +/- 0.2 uM details
Detected and Quantified8.82 +/- 0.03 uM details
Detected and Quantified4.1 +/- 0.1 uM details
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB 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.