Record Information
Version1.0
Creation date2011-09-21 00:12:02 UTC
Update date2019-11-26 03:21:02 UTC
Primary IDFDB022317
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameCE(18:1(9Z))
DescriptionCholesteryl oleate 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). Cholesteryl esters, formed by the esterification of cholesterol with long-chain fatty acids, on one hand, are the means by which cholesterol is transported through the blood by lipoproteins, on the other, the way cholesterol itself can be accumulated in the cells. (PMID: 15939411) [HMDB]
CAS Number303-43-5
Structure
Thumb
Synonyms
SynonymSource
Cholesteryl oleate, (e)-isomerMeSH
Cholesteryl oleateMeSH
(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-octadecenoateChEBI
(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
1-oleoyl-cholesterolhmdb
18:1 Cholesteryl esterChEBI
18:1(9Z) Cholesterol esterhmdb
3beta-Hydroxy-5-cholestene 3-oleatehmdb
5-Cholesten-3b-ol 3-oleatehmdb
CE(18:1)ChEBI
CE(18:1/0:0)HMDB
CE(18:1n9/0:0)hmdb
CE(18:1w9/0:0)hmdb
Cholest-5-en-3-b-yl oleateGenerator
Cholest-5-en-3-b-yl oleic acidGenerator
Cholest-5-en-3-beta-yl oleatehmdb
Cholest-5-en-3-beta-yl oleic acidGenerator
Cholest-5-en-3-ol (3b)-(Z)-9-octadecenoatehmdb
Cholest-5-en-3-ol (3b)-(Z)-9-octadecenoic acidhmdb
Cholest-5-en-3-yl (9Z)-9-octadecenoateChEBI
Cholest-5-en-3-yl (9Z)-9-octadecenoic acidGenerator
Cholest-5-en-3-β-yl oleateGenerator
Cholest-5-en-3-β-yl oleic acidGenerator
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 (9Z-octadecenoate)ChEBI
Cholesteryl (9Z-octadecenoic acid)Generator
Cholesteryl [9,10-3H]oleatehmdb
cholesteryl 1-oleoatehmdb
cholesteryl 1-oleoic acidhmdb
Cholesteryl cis-9-octadecenoatehmdb
Cholesteryl cis-9-octadecenoic acidhmdb
Cholesteryl oleate-9,10-3Hhmdb
Cholesteryl oleate-9,10-t2hmdb
CHOLESTERYL oleic acidGenerator
Cholesteryl oleic esterhmdb
Cholesteryl-beta-D-glucosidehmdb
Cholesteryl-beta-delta-glucosidehmdb
Oleic acid cholesteryl esterhmdb
Oleoylcholesterolhmdb
Predicted Properties
PropertyValueSource
Water Solubility6.3e-06 g/LALOGPS
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
Polarizability87.33 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC45H78O2
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 octadec-9-enoate
InChI IdentifierInChI=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/t36-,38+,39+,40-,41+,42+,44+,45-/m1/s1
InChI KeyRJECHNNFRHZQKU-XNTGVSEISA-N
Isomeric SMILES[H][C@@](C)(CCCC(C)C)[C@@]1([H])CC[C@@]2([H])[C@]3([H])CC=C4C[C@]([H])(CC[C@]4(C)[C@@]3([H])CC[C@]12C)OC(=O)CCCCCCCC=CCCCCCCCC
Average Molecular Weight651.0996
Monoisotopic Molecular Weight650.60018174
Classification
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
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
SpectraNot Available
ChemSpider ID4446726
ChEMBL IDCHEMBL1097567
KEGG Compound IDC14641
Pubchem Compound ID5283632
Pubchem Substance IDNot Available
ChEBI ID46898
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB00918
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET ID2OB
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Liver carboxylesterase 1CES1P23141
Lysosomal acid lipase/cholesteryl ester hydrolaseLIPAP38571
Sterol O-acyltransferase 1SOAT1P35610
Phosphatidylcholine-sterol acyltransferaseLCATP04180
Sterol O-acyltransferase 2SOAT2O75908
Scavenger receptor class B member 1SCARB1Q8WTV0
Neutral cholesterol ester hydrolase 1NCEH1Q6PIU2
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference