You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2006-08-13 05:23:04 UTC
Update Date2020-02-26 21:24:47 UTC
HMDB IDHMDB0003822
Secondary Accession Numbers
  • HMDB03822
Metabolite Identification
Common NameCholesteryl acetate
DescriptionCholesteryl acetate is a normal human cholesteryl ester present in diverse fluids and organs. Cholesteryl acetate is also present in foods. Food oxidation affects the quality and safety of the human diet by generating compounds with biological activities that can adversely affect health. In particular the susceptibility of cholesterol to oxidation is well known; certain products of cholesterol oxidation have been reported to produce cytotoxic, angiotoxic and carcinogenic effects. Cholesteryl ester (CE) is the major transport and storage form of cholesterol in lipoprotein particles and most cell types. Molecular composition of CE species is of high interest for arteriosclerosis research, i.e., as components of lipoprotein subclasses or in studies investigating the mechanisms involved in the generation of lipid laden foam cells. Thus, it has been shown that CE species in circulating plasma are strongly correlated with development of coronary heart disease. This may be related to specific CE species profiles generated by enzymes involved in lipoprotein metabolism like lecithin:cholesterol acyltransferase (EC 2.3.1.43, LCAT), acyl-coenzyme A:cholesterol acyltransferase 2 (EC 2.3.1.26, ACAT2) or cholesteryl ester transfer protein (CETP). The cholesteryl ester transfer protein has a key role in the metabolism of high-density lipoprotein (HDL), mediating the exchange of lipids between lipoproteins, resulting in the net transfer of cholesteryl ester from HDL to other lipoproteins and in the subsequent uptake of cholesterol by hepatocytes. By increasing the cholesteryl ester content of low-density and very-low-density lipoproteins, CETP promotes the atherogenicity of these lipoproteins. In addition, high plasma concentrations of CETP are associated with reduced concentrations of HDL cholesterol. (PMID: 10918380 , 16458590 , 9420339 , 3343104 , 6721900 , 7278520 ).
Structure
Data?1582752287
Synonyms
ValueSource
2-MethylacetoacetateGenerator
2-Methyl-3-oxo-butyric acidHMDB
2-Methyl-3-oxo-butyrateHMDB
2Methyl-3-ketovalerateHMDB
(+/-)-2-methyl-3-oxobutanoateHMDB
(+/-)-2-methyl-3-oxobutanoic acidHMDB
2-Acetylpropionic acidHMDB
2-Methyl-3-ketobutyric acidHMDB
2-Methyl-3-oxo-butanoateHMDB
2-Methyl-3-oxo-butanoic acidHMDB
2-Methyl-3-oxobutanoateHMDB
2-Methyl-3-oxobutanoic acidHMDB
2-Methyl-3-oxobutyric acidHMDB
2-Methyl-acetoacetic acidHMDB
3-oxo-2-Methylbutyric acidHMDB
a-Methylacetoacetic acidHMDB
alpha-MethylacetoacetateHMDB
alpha-Methylacetoacetic acidHMDB
(-)-2-Methyl-3-oxobutanoic acidHMDB
(2S)-2-Methyl-3-oxobutanoic acidHMDB
(S)-2-Acetylpropionic acidHMDB
(S)-2-Methyl-3-oxobutyric acidHMDB
(±)-2-methyl-3-oxobutanoic acidHMDB
3-Keto-2-methylbutyrateHMDB
3-Keto-2-methylbutyric acidHMDB
Α-methylacetoacetic acidHMDB
(-)-Cholesteryl acetateHMDB
(3b)-Cholest-5-en-3-ol acetateHMDB
3-Cholesteryl acetateHMDB
3b-Acetoxycholest-5-eneHMDB
Cholest-5-en-3b-ol acetateHMDB
Cholest-5-en-3b-yl acetateHMDB
Cholesterin acetateHMDB
Cholesterol 3-acetateHMDB
Cholesterol 3b-acetateHMDB
Cholesterol acetateHMDB
(2R,5S,15R)-2,15-Dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-yl acetic acidGenerator, HMDB
Cholesteryl acetateMeSH
Cholesteryl acetic acidGenerator
Chemical FormulaC29H48O2
Average Molecular Weight428.6902
Monoisotopic Molecular Weight428.36543078
IUPAC Name(2R,5S,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-yl acetate
Traditional Name(2R,5S,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-yl acetate
CAS Registry Number604-35-3
SMILES
CC(C)CCC[C@@H](C)C1CCC2C3CC=C4C[C@H](CC[C@]4(C)C3CC[C@]12C)OC(C)=O
InChI Identifier
InChI=1S/C29H48O2/c1-19(2)8-7-9-20(3)25-12-13-26-24-11-10-22-18-23(31-21(4)30)14-16-28(22,5)27(24)15-17-29(25,26)6/h10,19-20,23-27H,7-9,11-18H2,1-6H3/t20-,23+,24?,25?,26?,27?,28+,29-/m1/s1
InChI KeyXUGISPSHIFXEHZ-JUTJDYIZSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as short-chain keto acids and derivatives. These are keto acids with an alkyl chain the contains less than 6 carbon atoms.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassKeto acids and derivatives
Sub ClassShort-chain keto acids and derivatives
Direct ParentShort-chain keto acids and derivatives
Alternative Parents
Substituents
  • Beta-keto acid
  • Branched fatty acid
  • Methyl-branched fatty acid
  • Short-chain keto acid
  • Beta-hydroxy ketone
  • Fatty acyl
  • 1,3-dicarbonyl compound
  • Ketone
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organooxygen compound
  • Organic oxide
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

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 Solubility1.4e-05 g/LALOGPS
logP7.4ALOGPS
logP7.55ChemAxon
logS-7.5ALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity129.77 m³·mol⁻¹ChemAxon
Polarizability54.7 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-02bf-2109300000-d3daeef50bbce5584939Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004r-1009700000-75bb09e926fdb5ac7c0aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05p9-3009100000-d5a2ee8dce72d331e392Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6r-3129100000-9dab52e2d47a8e71712eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004r-1005900000-4fa7cbcd3c7c1e4d6fe6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002r-3009400000-53d27c9208e07f1d2a86Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-066r-5009000000-d9a319830de6f045f243Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023226
KNApSAcK IDNot Available
Chemspider ID24191898
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound150996
PDB IDNot Available
ChEBI ID37079
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Pelillo M, Galletti G, Lercker G: Mass spectral fragmentations of cholesterol acetate oxidation products. Rapid Commun Mass Spectrom. 2000;14(14):1275-9. [PubMed:10918380 ]
  2. Liebisch G, Binder M, Schifferer R, Langmann T, Schulz B, Schmitz G: High throughput quantification of cholesterol and cholesteryl ester by electrospray ionization tandem mass spectrometry (ESI-MS/MS). Biochim Biophys Acta. 2006 Jan;1761(1):121-8. Epub 2006 Jan 18. [PubMed:16458590 ]
  3. Kuivenhoven JA, Jukema JW, Zwinderman AH, de Knijff P, McPherson R, Bruschke AV, Lie KI, Kastelein JJ: The role of a common variant of the cholesteryl ester transfer protein gene in the progression of coronary atherosclerosis. The Regression Growth Evaluation Statin Study Group. N Engl J Med. 1998 Jan 8;338(2):86-93. [PubMed:9420339 ]
  4. Nicolaides N, Flores A, Santos EC, Robin JB, Smith RE: The lipids of chalazia. Invest Ophthalmol Vis Sci. 1988 Mar;29(3):482-6. [PubMed:3343104 ]
  5. Dolphin PJ, Breckenridge WC, Dolphin MA, Tan MH: The lipoproteins of human umbilical cord blood apolipoprotein and lipid levels. Atherosclerosis. 1984 Apr;51(1):109-22. [PubMed:6721900 ]
  6. Perkins EG, Hendren DJ, Bauer JE, El-Hamdy AH: High performance reversed phase chromatography of cholesterol and cholesteryl esters of human plasma lipoproteins. Lipids. 1981 Aug;16(8):609-13. [PubMed:7278520 ]

Enzymes

General function:
Involved in phosphatidylcholine-sterol O-acyltransferase activity
Specific function:
Central enzyme in the extracellular metabolism of plasma lipoproteins. Synthesized mainly in the liver and secreted into plasma where it converts cholesterol and phosphatidylcholines (lecithins) to cholesteryl esters and lysophosphatidylcholines on the surface of high and low density lipoproteins (HDLs and LDLs). The cholesterol ester is then transported back to the liver. Has a preference for plasma 16:0-18:2 or 18:O-18:2 phosphatidylcholines. Also produced in the brain by primary astrocytes, and esterifies free cholesterol on nascent APOE-containing lipoproteins secreted from glia and influences cerebral spinal fluid (CSF) APOE- and APOA1 levels. Together with APOE and the cholesterol transporter ABCA1, plays a key role in the maturation of glial-derived, nascent lipoproteins. Required for remodeling high-density lipoprotein particles into their spherical forms.
Gene Name:
LCAT
Uniprot ID:
P04180
Molecular weight:
49577.545
General function:
Involved in lipid metabolic process
Specific function:
Crucial for the intracellular hydrolysis of cholesteryl esters and triglycerides that have been internalized via receptor-mediated endocytosis of lipoprotein particles. Important in mediating the effect of LDL (low density lipoprotein) uptake on suppression of hydroxymethylglutaryl-CoA reductase and activation of endogenous cellular cholesteryl ester formation.
Gene Name:
LIPA
Uniprot ID:
P38571
Molecular weight:
45418.71
General function:
Lipid transport and metabolism
Specific function:
Catalyzes fat and vitamin absorption. Acts in concert with pancreatic lipase and colipase for the complete digestion of dietary triglycerides.
Gene Name:
CEL
Uniprot ID:
P19835
Molecular weight:
79666.385
General function:
Lipid transport and metabolism
Specific function:
Involved in the detoxification of xenobiotics and in the activation of ester and amide prodrugs. Hydrolyzes aromatic and aliphatic esters, but has no catalytic activity toward amides or a fatty acyl-CoA ester. Hydrolyzes the methyl ester group of cocaine to form benzoylecgonine. Catalyzes the transesterification of cocaine to form cocaethylene. Displays fatty acid ethyl ester synthase activity, catalyzing the ethyl esterification of oleic acid to ethyloleate.
Gene Name:
CES1
Uniprot ID:
P23141
Molecular weight:
62520.62
General function:
Involved in acyl-CoA binding
Specific function:
Plays a role in lipoprotein assembly and dietary cholesterol absorption. In addition to its acyltransferase activity, it may act as a ligase. May provide cholesteryl esters for lipoprotein secretion from hepatocytes and intestinal mucosa.
Gene Name:
SOAT2
Uniprot ID:
O75908
Molecular weight:
59895.735
General function:
Involved in acyl-CoA binding
Specific function:
Catalyzes the formation of fatty acid-cholesterol esters. Plays a role in lipoprotein assembly and dietary cholesterol absorption. In addition to its acyltransferase activity, it may act as a ligase.
Gene Name:
SOAT1
Uniprot ID:
P35610
Molecular weight:
58130.665