| 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 |
Download:
MOL |
SDF |
SMILES |
InChI
Display:
2D Structure |
3D Structure
|
| Synonyms |
- 1-Stearoyl-cholesterol
- 18:0 Cholesterol ester
- CE(18:0)
- CE(18:0/0:0)
- Cholesterol 1-octadecanoate
- Cholesterol 1-octadecanoic acid
- Cholesterol 1-stearoate
- Cholesterol 1-stearoic acid
- Cholesterol Ester(18:0)
- Cholesterol Ester(18:0/0:0)
- Cholesteryl 1-octadecanoate
- Cholesteryl 1-octadecanoic acid
- Cholesteryl 1-stearoate
- 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 |
|
| Biofunction |
- Cell signaling
- Energy source
- Fuel and energy storage
- Fuel or energy source
- Membrane component
- Membrane integrity/stability
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| Application |
- Nutrients
- Stabilizers
- Surfactants and Emulsifiers
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| Cellular locations |
|
| 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 |
|
| Spectra |
|---|
|
Not Available
|
| Biological Properties |
|---|
| Cellular Locations |
|
| Biofluid Locations |
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| Tissue Location |
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| Pathways |
Not Available
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| Normal Concentrations |
|---|
|
| Blood |
Detected and Quantified |
|
37.50 +/- 2.81 uM |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Blood |
Detected and Quantified |
|
59 +/- 3 uM |
Adult (>18 years old) |
Both |
Normal |
Not Available |
|
| Abnormal Concentrations |
|---|
|
Not Available |
| Associated Disorders and Diseases |
|---|
| Disease References |
None |
| Associated OMIM IDs |
None |
| External Links |
|---|
| DrugBank 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  |
| KEGG Compound ID |
C02530 |
| BioCyc ID |
Cholesterol-esters |
| BiGG ID |
Not Available |
| Wikipedia Link |
Not Available |
| NuGOwiki Link |
HMDB10368 |
| Metagene Link |
HMDB10368 |
| METLIN ID |
5898 |
| PubChem Compound |
53480457 |
| PDB ID |
Not Available |
| ChEBI ID |
Not Available |
| References |
|---|
| Synthesis Reference |
Not Available |
| Material Safety Data Sheet (MSDS) |
Not Available
|
| General References |
- 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
- Denke MA: Dietary fats, fatty acids, and their effects on lipoproteins. Curr Atheroscler Rep. 2006 Nov;8(6):466-71.
Pubmed: 17045072
- Mensink RP: Effects of stearic acid on plasma lipid and lipoproteins in humans. Lipids. 2005 Dec;40(12):1201-5.
Pubmed: 16477803
|
