Record Information
Version3.6
Creation Date2008-09-16 13:19:42 UTC
Update Date2013-02-09 00:24:40 UTC
HMDB IDHMDB10368
Secondary Accession NumbersNone
Metabolite Identification
Common NameCE(18:0)
DescriptionCE(18:0) 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.
Structure
Thumb
Synonyms
  1. 1-Stearoyl-cholesterol
  2. 18:0 Cholesterol ester
  3. CE(18:0)
  4. CE(18:0/0:0)
  5. Cholesterol 1-octadecanoate
  6. Cholesterol 1-octadecanoic acid
  7. Cholesterol 1-stearoate
  8. Cholesterol 1-stearoic acid
  9. Cholesterol Ester(18:0)
  10. Cholesterol Ester(18:0/0:0)
  11. Cholesteryl 1-octadecanoate
  12. Cholesteryl 1-octadecanoic acid
  13. Cholesteryl 1-stearoate
  14. Cholesteryl 1-stearoic acid
Chemical FormulaC45H80O2
Average Molecular Weight653.1155
Monoisotopic Molecular Weight652.615831804
IUPAC Name(2R,5S,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 octadecanoate
Traditional IUPAC Name(2R,5S,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 octadecanoate
CAS Registry NumberNot Available
SMILES
CCCCCCCCCCCCCCCCCC(=O)O[C@H]1CC[C@]2(C)C3CC[C@]4(C)C(CCC4C3CC=C2C1)[C@H](C)CCCC(C)C
InChI Identifier
InChI=1S/C45H80O2/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/h26,35-36,38-42H,7-25,27-34H2,1-6H3/t36-,38+,39?,40?,41?,42?,44+,45-/m1/s1
InChI KeyXHRPOTDGOASDJS-GHOVPUJYSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassLipids
ClassSteroids and Steroid Derivatives
Sub ClassSteroid Esters
Other Descriptors
  • Aliphatic Homopolycyclic Compounds
  • Branched Fatty Acids
  • Carbocyclic Fatty Acids
  • Organic Compounds
  • Triterpenes
  • Unsaturated Fatty Acids
Substituents
  • Bicyclohexane
  • Carboxylic Acid Ester
  • Cyclohexane
  • Cyclohexene
Direct ParentCholesteryl Esters
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Energy source
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane component
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
water solubility7.100E-06 g/LALOGPS
logP10.79ALOGPS
logP14.92ChemAxon
logS-8ALOGPS
pKa (strongest basic)-7ChemAxon
physiological charge0ChemAxon
hydrogen acceptor count1ChemAxon
hydrogen donor count0ChemAxon
polar surface area26.3ChemAxon
rotatable bond count23ChemAxon
refractivity203.41ChemAxon
polarizability87.99ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
Tissue Location
  • All Tissues
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReference
BloodDetected and Quantified37.50 +/- 2.81 uMAdult (>18 years old)BothNormal
BloodDetected and Quantified59 +/- 3 uMAdult (>18 years old)BothNormal
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB027520
KNApSAcK IDNot Available
Chemspider ID24769460
KEGG Compound IDC02530
BioCyc IDCholesterol-esters
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB10368
Metagene LinkHMDB10368
METLIN ID5898
PubChem Compound53480457
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Ekman S, Lundberg B: The transfer of lipids from protein-free lipoprotein models to human fibroblasts in culture. Biochim Biophys Acta. 1987 Sep 25;921(2):347-55. Pubmed: 3651492
  2. Denke MA: Dietary fats, fatty acids, and their effects on lipoproteins. Curr Atheroscler Rep. 2006 Nov;8(6):466-71. Pubmed: 17045072
  3. Mensink RP: Effects of stearic acid on plasma lipid and lipoproteins in humans. Lipids. 2005 Dec;40(12):1201-5. Pubmed: 16477803

Enzymes

Gene Name:
CEL
Uniprot ID:
P19835
Gene Name:
CES1
Uniprot ID:
P23141
Gene Name:
SOAT2
Uniprot ID:
O75908
Gene Name:
SOAT1
Uniprot ID:
P35610
Gene Name:
SCARB1
Uniprot ID:
Q8WTV0