| Record Information |
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| Version | 1.0 |
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| Creation date | 2011-09-21 00:26:37 UTC |
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| Update date | 2015-07-21 06:57:36 UTC |
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| Primary ID | FDB023229 |
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| Secondary Accession Numbers | Not Available |
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| Chemical Information |
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| FooDB Name | Cholesteryl acetate |
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| Description | Cholesteryl 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) [HMDB] |
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| CAS Number | 604-35-3 |
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| Structure | |
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| Synonyms | |
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| Predicted Properties | |
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| Chemical Formula | C29H48O2 |
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| 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 |
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| 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 |
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| InChI Key | XUGISPSHIFXEHZ-JUTJDYIZSA-N |
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| Isomeric SMILES | CC(C)CCC[C@@H](C)C1CCC2C3CC=C4C[C@H](CC[C@]4(C)C3CC[C@]12C)OC(C)=O |
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| Average Molecular Weight | 428.6902 |
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| Monoisotopic Molecular Weight | 428.36543078 |
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| Classification |
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| 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. |
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| Kingdom | Organic compounds |
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| Super Class | Organic acids and derivatives |
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| Class | Keto acids and derivatives |
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| Sub Class | Short-chain keto acids and derivatives |
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| Direct Parent | Short-chain keto acids and derivatives |
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| Alternative Parents | |
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| 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
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| Molecular Framework | Aliphatic acyclic compounds |
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| External Descriptors | Not Available |
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| Ontology |
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| Disposition | Route of exposure: Biological location: Source: |
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| Process | Naturally occurring process: |
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| Role | Biological role: Industrial application: |
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| Physico-Chemical Properties |
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| Physico-Chemical Properties - Experimental | |
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| Spectra |
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| Spectra | |
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| EI-MS/GC-MS | | Type | Description | Splash Key | View |
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| Predicted GC-MS | Cholesteryl acetate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-02bf-2109300000-d3daeef50bbce5584939 | Spectrum |
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| MS/MS | | Type | Description | Splash Key | View |
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| Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-004r-1009700000-75bb09e926fdb5ac7c0a | 2017-09-01 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-05p9-3009100000-d5a2ee8dce72d331e392 | 2017-09-01 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0a6r-3129100000-9dab52e2d47a8e71712e | 2017-09-01 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-004r-1005900000-4fa7cbcd3c7c1e4d6fe6 | 2017-09-01 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-002r-3009400000-53d27c9208e07f1d2a86 | 2017-09-01 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-066r-5009000000-d9a319830de6f045f243 | 2017-09-01 | View Spectrum |
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| NMR | Not Available |
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| External Links |
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| ChemSpider ID | 4932701 |
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| ChEMBL ID | Not Available |
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| KEGG Compound ID | C02530 |
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| Pubchem Compound ID | 6427285 |
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| Pubchem Substance ID | Not Available |
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| ChEBI ID | Not Available |
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| Phenol-Explorer ID | Not Available |
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| DrugBank ID | Not Available |
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| HMDB ID | HMDB03822 |
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| CRC / DFC (Dictionary of Food Compounds) ID | Not Available |
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| EAFUS ID | Not Available |
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| Dr. Duke ID | Not Available |
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| BIGG ID | Not Available |
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| KNApSAcK ID | Not Available |
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| HET ID | Not Available |
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| Food Biomarker Ontology | Not Available |
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| VMH ID | Not Available |
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| Flavornet ID | Not Available |
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| GoodScent ID | Not Available |
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| SuperScent ID | Not Available |
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| Wikipedia ID | Not Available |
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| Phenol-Explorer Metabolite ID | Not Available |
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| Duplicate IDS | Not Available |
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| Old DFC IDS | Not Available |
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| Associated Foods |
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| Biological Effects and Interactions |
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| Health Effects / Bioactivities | Not Available |
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| Enzymes | |
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| Pathways | Not Available |
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| Metabolism | Not Available |
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| Biosynthesis | Not Available |
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| Organoleptic Properties |
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| Flavours | Not Available |
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| Files |
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| MSDS | show |
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| References |
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| Synthesis Reference | Not Available |
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| General Reference | Not Available |
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| Content Reference | |
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