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Showing Compound CE(18:3(9Z,12Z,15Z)) (FDB027522)

Record Information
Version1.0
Creation date2011-09-21 01:25:50 UTC
Update date2015-10-09 22:33:34 UTC
Primary IDFDB027522
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameCE(18:3(9Z,12Z,15Z))
DescriptionCE(18:3(9Z,12Z,15Z)) is a cholesterol fatty acid ester or simply a cholesterol ester (CE). Cholesterol esters are cholesterol molecules with long-chain fatty acids linked to the hydroxyl group. They are much less polar than free cholesterol and appear to be the preferred form for transport in plasma and for storage. Cholesterol esters do not contribute to membranes but are packed into intracellular lipid particles or lipoprotein particles. Because of the mechanism of synthesis, plasma cholesterol esters tend to contain relatively high proportions of C18 fatty acids. Cholesterol esters are major constituents of the adrenal glands and they also accumulate in the fatty lesions of atherosclerotic plaques. Cholesterol esters are also major constituents of the lipoprotein particles carried in blood (HDL, LDL, VLDL). The cholesterol esters in high-density lipoproteins (HDL) are synthesized largely by transfer of fatty acids to cholesterol from position sn-2 (or C-2) of phosphatidylcholine catalyzed by the enzyme lecithin cholesterol acyl transferase (LCAT). The enzyme also promotes the transfer of cholesterol from cells to HDL. As cholesterol esters accumulate in the lipoprotein core, cholesterol is removed from its surface thus promoting the flow of cholesterol from cell membranes into HDL. This in turn leads to morphological changes in HDL, which grow and become spherical. Subsequently, cholesterol esters are transferred to the other lipoprotein fractions LDL and VLDL, a reaction catalyzed by cholesteryl ester transfer protein. Another enzyme, acyl-CoA:cholesterol acyltransferase (ACAT) synthesizes cholesterol esters from CoA esters of fatty acids and cholesterol. Cholesterol ester hydrolases liberate cholesterol and free fatty acids when required for membrane and lipoprotein formation, and they also provide cholesterol for hormone synthesis in adrenal cells. [HMDB]
CAS Number2545-22-4
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
(3b) Cholest 5 en 3 ol (Z,Z,Z) octadecatrienoatehmdb
(3b) Cholest 5 en 3 ol (Z,Z,Z) octadecatrienoic acidhmdb
1-a-linolenoyl-cholesterolhmdb
1-alpha-linolenoyl-cholesterolhmdb
18:3 Cholesteryl esterChEBI
18:3(9Z,12Z,15Z) cholesterol esterhmdb
CE(18:3n3/0:0)hmdb
CE(18:3w3/0:0hmdb
Cholest 5 en 3beta yl (Z,Z,Z) octadeca 9,12,15 trien 1 oatehmdb
Cholest 5 en 3beta yl (Z,Z,Z) octadeca 9,12,15 trien 1 oic acidhmdb
cholesterol 1-(9Z,12Z,15Z-octadeatrienoatehmdb
cholesterol 1-(9Z,12Z,15Z-octadeatrienoate)hmdb
cholesterol 1-(9Z,12Z,15Z-octadeatrienoic acidhmdb
cholesterol 1-(9Z,12Z,15Z-octadeatrienoic acid)hmdb
cholesterol 1-a-linolenoatehmdb
cholesterol 1-a-linolenoic acidhmdb
cholesterol 1-alpha-linolenoatehmdb
cholesterol 1-alpha-linolenoic acidhmdb
Cholesterol a linolenatehmdb
Cholesterol alpha linolenatehmdb
Cholesterol Ester(18:3n3/0:0)hmdb
Cholesterol Ester(18:3w3/0:0)hmdb
Cholesterol linolenatehmdb
Cholesterol octadecatrienoatehmdb
Cholesterol octadecatrienoic acidhmdb
Cholesteryl (9Z,12Z,15Z)-octadeca-9,12,15-trienoateChEBI
Cholesteryl (9Z,12Z,15Z)-octadeca-9,12,15-trienoic acidGenerator
cholesteryl 1-(9Z,12Z,15Z-octadeatrienoatehmdb
cholesteryl 1-(9Z,12Z,15Z-octadeatrienoate)hmdb
cholesteryl 1-(9Z,12Z,15Z-octadeatrienoic acidhmdb
cholesteryl 1-(9Z,12Z,15Z-octadeatrienoic acid)hmdb
cholesteryl 1-a-linolenoatehmdb
cholesteryl 1-a-linolenoic acidhmdb
cholesteryl 1-alpha-linolenoatehmdb
cholesteryl 1-alpha-linolenoic acidhmdb
Cholesteryl linolenatehmdb
Cholesteryl linolenic acidhmdb
Cholesteryl octadecatrienoatehmdb
Cholesteryl octadecatrienoic acidhmdb
Linolenic acid cholesteryl esterhmdb
Predicted Properties
PropertyValueSource
Water Solubility5.8e-06 g/LALOGPS
logP10.24ALOGPS
logP13.84ChemAxon
logS-8ALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count20ChemAxon
Refractivity206.76 m³·mol⁻¹ChemAxon
Polarizability85.69 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC45H74O2
IUPAC name(1S,2R,5S,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-yl octadeca-9,12,15-trienoate
InChI IdentifierInChI=1S/C45H74O2/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/h8-9,11-12,14-15,26,35-36,38-42H,7,10,13,16-25,27-34H2,1-6H3/t36-,38+,39+,40-,41+,42+,44+,45-/m1/s1
InChI KeyFYMCIBHUFSIWCE-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=CCC=CCC
Average Molecular Weight647.0679
Monoisotopic Molecular Weight646.568881612
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 DescriptorsNot Available
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 ID4941513
ChEMBL IDNot Available
KEGG Compound IDC02530
Pubchem Compound ID6436907
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB10370
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
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
MSDSNot Available
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.