Human Metabolome Database Version 3.5

Showing metabocard for CE(18:0) (HMDB10368)

Record Information
Version 3.5
Creation Date 2008-09-16 07:19:42 -0600
Update Date 2013-02-08 17:24:40 -0700
HMDB ID HMDB10368
Secondary Accession Numbers None
Metabolite Identification
Common Name CE(18:0)
Description CE(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
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
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 Formula C45H80O2
Average Molecular Weight 653.1155
Monoisotopic Molecular Weight 652.615831804
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 Number Not 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 Key XHRPOTDGOASDJS-GHOVPUJYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Steroids and Steroid Derivatives
Sub Class Steroid 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 Parent Cholesteryl Esters
Ontology
Status Detected 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
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
LogP 10.79 ALOGPS
LogP 14.92 ChemAxon
LogS -7.96 ALOGPS
pKa (strongest basic) -7 ChemAxon
Hydrogen Acceptor Count 1 ChemAxon
Hydrogen Donor Count 0 ChemAxon
Polar Surface Area 26.3 A2 ChemAxon
Rotatable Bond Count 23 ChemAxon
Refractivity 203.41 ChemAxon
Polarizability 87.99 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
Tissue Location
  • All Tissues
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified
37.50 +/- 2.81 uM Adult (>18 years old) Both Normal
Blood Detected and Quantified
59 +/- 3 uM Adult (>18 years old) Both Normal
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB027520
KNApSAcK ID Not Available
Chemspider ID 24769460 Link_out
KEGG Compound ID C02530 Link_out
BioCyc ID Cholesterol-esters Link_out
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB10368 Link_out
Metagene Link HMDB10368 Link_out
METLIN ID 5898 Link_out
PubChem Compound 53480457 Link_out
PDB ID Not Available
ChEBI ID Not Available
References
Synthesis Reference Not 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 Link_out
  2. Denke MA: Dietary fats, fatty acids, and their effects on lipoproteins. Curr Atheroscler Rep. 2006 Nov;8(6):466-71. Pubmed: 17045072 Link_out
  3. Mensink RP: Effects of stearic acid on plasma lipid and lipoproteins in humans. Lipids. 2005 Dec;40(12):1201-5. Pubmed: 16477803 Link_out

Enzymes
Name: Phosphatidylcholine-sterol acyltransferase
Reactions: Not Available
Gene Name: LCAT
Uniprot ID: P04180 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Lysosomal acid lipase/cholesteryl ester hydrolase
Reactions: Not Available
Gene Name: LIPA
Uniprot ID: P38571 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Bile salt-activated lipase
Reactions: Not Available
Gene Name: CEL
Uniprot ID: P19835 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Liver carboxylesterase 1
Reactions: Not Available
Gene Name: CES1
Uniprot ID: P23141 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Sterol O-acyltransferase 2
Reactions: Not Available
Gene Name: SOAT2
Uniprot ID: O75908 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Sterol O-acyltransferase 1
Reactions: Not Available
Gene Name: SOAT1
Uniprot ID: P35610 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Scavenger receptor class B member 1
Reactions: Not Available
Gene Name: SCARB1
Uniprot ID: Q8WTV0 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Neutral cholesterol ester hydrolase 1
Reactions: Not Available
Gene Name: NCEH1
Uniprot ID: Q6PIU2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA