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Showing Compound CE(18:2(9Z,12Z)) (FDB022141)

Record Information
Version1.0
Creation date2011-09-21 00:09:05 UTC
Update date2019-11-26 03:21:01 UTC
Primary IDFDB022141
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameCE(18:2(9Z,12Z))
DescriptionCholesteryl linoleic acid is a cholesteryl ester. 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). Cholesteryl linoleate is contained in low density lipoprotein and atherosclerotic lesions. The oxidation products of cholesteryl linoleate may cause chronic inflammatory processes. (PMID 9684755, 11950694) [HMDB]
CAS Number604-33-1
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Cholesteryl trans-9-trans-12-octadecadienoateMeSH
Cholesteryl linoleateMeSH
Cholesteryl linoleate, (e,Z)-isomerMeSH
Cholesteryl linolelaidateMeSH
Cholesteryl linoleate, (e,e)-isomerMeSH
Cholesteryl linoleate, (Z,e)-isomerMeSH
CLOHMeSH
(3b)-Cholest-5-en-3-ol, (9Z,12Z)-9,12-octadecadienoateGenerator
(3b)-Cholest-5-en-3-ol, (9Z,12Z)-9,12-octadecadienoic acidGenerator
(3b)-Cholest-5-en-3-ol, (Z,Z)-9,12-octadecadienoateGenerator
(3b)-Cholest-5-en-3-ol, (Z,Z)-9,12-octadecadienoic acidGenerator
(3beta)-Cholest-5-en-3-ol, (9Z,12Z)-9,12-octadecadienoateChEBI
(3beta)-Cholest-5-en-3-ol, (9Z,12Z)-9,12-octadecadienoic acidGenerator
(3beta)-Cholest-5-en-3-ol, (Z,Z)-9,12-octadecadienoateChEBI
(3beta)-Cholest-5-en-3-ol, (Z,Z)-9,12-octadecadienoic acidGenerator
(3β)-cholest-5-en-3-ol, (9Z,12Z)-9,12-octadecadienoateGenerator
(3β)-cholest-5-en-3-ol, (9Z,12Z)-9,12-octadecadienoic acidGenerator
(3β)-cholest-5-en-3-ol, (Z,Z)-9,12-octadecadienoateGenerator
(3β)-cholest-5-en-3-ol, (Z,Z)-9,12-octadecadienoic acidGenerator
(Z,Z)-(3b)-Cholest-5-en-3-ol 9,12-octadecadienoateGenerator
(Z,Z)-(3b)-Cholest-5-en-3-ol 9,12-octadecadienoic acidGenerator
(Z,Z)-(3beta)-Cholest-5-en-3-ol 9,12-octadecadienoateChEBI
(Z,Z)-(3beta)-Cholest-5-en-3-ol 9,12-octadecadienoic acidGenerator
(Z,Z)-(3β)-cholest-5-en-3-ol 9,12-octadecadienoateGenerator
(Z,Z)-(3β)-cholest-5-en-3-ol 9,12-octadecadienoic acidGenerator
1-linoleoyl-cholesterolhmdb
18:2 Cholesteryl esterChEBI
18:2(9Z,12Z) Cholesterol esterhmdb
CE(18:2)hmdb
CE(18:2/0:0)hmdb
CE(18:2n6/0:0)hmdb
CE(18:2w6/0:0)hmdb
Cholest-5-en-3b-yl (Z,Z)-octadeca-9,12-dienoateGenerator
Cholest-5-en-3b-yl (Z,Z)-octadeca-9,12-dienoic acidGenerator
cholest-5-en-3beta-yl (9Z,12Z-octadecadienoatehmdb
cholest-5-en-3beta-yl (9Z,12Z-octadecadienoate)hmdb
cholest-5-en-3beta-yl (9Z,12Z-octadecadienoic acidhmdb
Cholest-5-en-3beta-yl (Z,Z)-octadeca-9,12-dienoateChEBI
Cholest-5-en-3beta-yl (Z,Z)-octadeca-9,12-dienoic acidGenerator
Cholest-5-en-3β-yl (Z,Z)-octadeca-9,12-dienoateGenerator
Cholest-5-en-3β-yl (Z,Z)-octadeca-9,12-dienoic acidGenerator
cholesterol 1-(9Z,12Z-octadecadienoatehmdb
cholesterol 1-(9Z,12Z-octadecadienoate)hmdb
cholesterol 1-(9Z,12Z-octadecadienoic acidhmdb
cholesterol 1-(9Z,12Z-octadecadienoic acid)hmdb
cholesterol 1-linoleoatehmdb
cholesterol 1-linoleoic acidhmdb
Cholesterol Ester(18:2)hmdb
Cholesterol Ester(18:2/0:0)hmdb
Cholesterol Ester(18:2n6/0:0)hmdb
Cholesterol Ester(18:2w6/0:0)hmdb
Cholesteryl (9Z,12Z-octadecadienoate)ChEBI
Cholesteryl (9Z,12Z-octadecadienoic acid)Generator
cholesteryl 1-(9Z,12Z-octadecadienoatehmdb
cholesteryl 1-(9Z,12Z-octadecadienoate)hmdb
cholesteryl 1-(9Z,12Z-octadecadienoic acidhmdb
cholesteryl 1-(9Z,12Z-octadecadienoic acid)hmdb
cholesteryl 1-linoleoatehmdb
cholesteryl 1-linoleoic acidhmdb
CHOLESTERYL linoleATEChEBI
CHOLESTERYL linoleic acidGenerator
Predicted Properties
PropertyValueSource
Water Solubility5.8e-06 g/LALOGPS
logP10.5ALOGPS
logP14.2ChemAxon
logS-8ALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count21ChemAxon
Refractivity205.64 m³·mol⁻¹ChemAxon
Polarizability86.31 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC45H76O2
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 octadeca-9,12-dienoate
InChI IdentifierInChI=1S/C45H76O2/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/h11-12,14-15,26,35-36,38-42H,7-10,13,16-25,27-34H2,1-6H3/t36-,38+,39+,40-,41+,42+,44+,45-/m1/s1
InChI KeyNAACPBBQTFFYQB-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=CCC=CCCCCC
Average Molecular Weight649.0837
Monoisotopic Molecular Weight648.584531676
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
  • Octadecanoid
  • 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
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 ID4450205
ChEMBL IDNot Available
KEGG Compound IDC15441
Pubchem Compound ID5287939
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB00610
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDCLL
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— U.S. Department of Agriculture, Agricultural Research Service. 2008. USDA National Nutrient Database for Standard Reference, Release 21. Nutrient Data Laboratory Home Page.