| Record Information |
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| Version | 1.0 |
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| Creation date | 2010-04-08 22:10:37 UTC |
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| Update date | 2019-11-26 03:08:14 UTC |
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| Primary ID | FDB013269 |
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| Secondary Accession Numbers | Not Available |
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| Chemical Information |
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| FooDB Name | Cholesterol |
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| Description | Constituent either free or as esters, of fish liver oils, lard, dairy fats, egg yolk and bran
About 20?25% of total daily cholesterol production occurs in the liver; other sites of high synthesis rates include the intestines, adrenal glands and reproductive organs. Synthesis within the body starts with one molecule of acetyl CoA and one molecule of acetoacetyl-CoA, which are dehydrated to form 3-hydroxy-3-methylglutaryl CoA (HMG-CoA). This molecule is then reduced to mevalonate by the enzyme HMG-CoA reductase. This step is an irreversible step in cholesterol synthesis and is the site of action for the statins (HMG-CoA Reductase Inhibitors).; Cholesterol is a lipidic, waxy steroid found in the cell membranes and transported in the blood plasma of all animals. It is an essential component of mammalian cell membranes where it is required to establish proper membrane permeability and fluidity. In addition, cholesterol is an important precursor molecule for the biosynthesis of bile acids, steroid hormones, and several fat soluble vitamins. Cholesterol is the principal sterol synthesized by animals, but small quantities are synthesized in other eukaryotes, such as plants and fungi. It is almost completely absent among prokaryotes, which include bacteria.; Cholesterol is a sterol (a combination steroid and alcohol) and a lipid found in the cell membranes of all body tissues, and transported in the blood plasma of all animals. The name originates from the Greek chole- (bile) and stereos (solid), and the chemical suffix -ol for an alcohol, as researchers first identified cholesterol (C27H45OH) in solid form in gallstones in 1784. Cholesterol is transported throughout the body via lipoprotein particles. The largest lipoproteins, which primarily transport fats from the intestinal mucosa to the liver, are called chylomicrons. They carry mostly triglyceride fats and cholesterol (that are from food and especially internal cholesterol secreted by the liver into the bile). In the liver, chylomicron particles give up triglycerides and some cholesterol, and are converted into low-density lipoprotein (LDL) particles, which carry triglycerides and cholesterol on to other body cells. In healthy individuals the LDL particles are large and relatively few in number. In contrast, large numbers of small LDL particles are strongly associated with promoting atheromatous disease within the arteries. (Lack of information on LDL particle number and size is one of the major problems of conventional lipid tests.). In conditions with elevated concentrations of oxidized LDL particles, especially small LDL particles, cholesterol promotes atheroma plaque deposits in the walls of arteries, a condition known as atherosclerosis, which is a major contributor to coronary heart disease and other forms of cardiovascular disease. (In contrast, HDL particles have been the only identified mechanism by which cholesterol can be removed from atheroma. Increased concentrations of large HDL particles, not total HDL particles, correlate with lower rates of atheroma progressions, even regression.). There is a world-wide trend to believe that lower total cholesterol levels tend to correlate with lower atherosclerosis event rates (though many studies refute this idea). Due to this reason, cholesterol has become a very large focus for scientific researchers trying to determine the proper amount of cholesterol needed in a healthy diet. However, the primary association of atherosclerosis with cholesterol has always been specifically with cholesterol transport patterns, not total cholesterol per se. For example, total cholesterol can be low, yet made up primarily of small LDL and small HDL particles and atheroma growth rates are high. In contrast, however, if LDL particle number is low (mostly large particles) and a large percentage of the HDL particles are large (HDL is actively reverse transporting cholesterol), then atheroma growth rates are usually low, even negative, for any given total cholesterol concentration. These effects are further complicated by the relative concentration of asymmetric dimethylarginin (ADMA) in the endothelium, since ADMA down-regulates production of nitric oxide, a relaxant of the endothelium. Thus, high levels of ADMA, associated with high oxidized levels of LDL pose a heightened risk factor for vascular disease. -- Wikipedia; Given the well-recognized role of cholesterol in cardiovascular disease, it is surprising that some studies have shown an inverse correlation between cholesterol levels and mortality in subjects over 50 years of age?an 11% increase overall and 14% increase in CVD mortality per 1 mg/dL per year drop in cholesterol levels. In the Framingham Heart Study, the researchers attributed this phenomenon to the fact that people with severe chronic diseases or cancer tend to have below-normal cholesterol levels. This explanation is not supported by the Vorarlberg Health Monitoring and Promotion Programme, in which men of all ages and women over 50 with very low cholesterol were increasingly likely to die of cancer, liver diseases, and mental diseases. This result indicates that the low cholesterol effect occurs even among younger respondents, contradicting the previous assessment among cohorts of older people that this is a proxy or marker for frailty occurring with age.; Mevalonate is then converted to 3-isopentenyl pyrophosphate in three reactions which require ATP. This molecule is decarboxylated to isopentenyl pyrophosphate, which is a key metabolite for various biological reactions. Three molecules of isopentenyl pyrophosphate condense to form farnesyl pyrophosphate through the action of geranyl transferase. Two molecules of farnesyl pyrophosphate then condense to form squalene by the action of squalene synthase in the endoplasmic reticulum. Oxidosqualene cyclase then cyclizes squalene to form lanosterol. Finally, lanosterol is then converted to cholesterol.; Within cells, cholesterol is the precursor molecule in several biochemical pathways. In the liver, cholesterol is converted to bile, which is then stored in the gallbladder. Bile contains bile salts, which solubilize fats in the digestive tract and aid in the intestinal absorption of fat molecules as well as the fat soluble vitamins, Vitamin A, Vitamin D, Vitamin E and Vitamin K. Cholesterol is an important precursor molecule for the synthesis of Vitamin D and the steroid hormones, including the adrenal gland hormones cortisol and aldosterone as well as the sex hormones progesterone, estrogens, and testosterone and their derivatives. |
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| CAS Number | 57-88-5 |
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| Structure | |
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| Synonyms | | Synonym | Source |
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| Not Available | Not Available |
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| Predicted Properties | |
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| Chemical Formula | C27H46O |
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| IUPAC name | 2,15-dimethyl-14-(6-methylheptan-2-yl)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-ol |
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| InChI Identifier | InChI=1S/C27H46O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h9,18-19,21-25,28H,6-8,10-17H2,1-5H3 |
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| InChI Key | HVYWMOMLDIMFJA-UHFFFAOYSA-N |
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| Isomeric SMILES | CC(C)CCCC(C)C1CCC2C3CC=C4CC(O)CCC4(C)C3CCC12C |
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| Average Molecular Weight | 386.6535 |
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| Monoisotopic Molecular Weight | 386.354866094 |
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| Classification |
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| Description | Belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core. |
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| Kingdom | Organic compounds |
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| Super Class | Lipids and lipid-like molecules |
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| Class | Steroids and steroid derivatives |
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| Sub Class | Cholestane steroids |
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| Direct Parent | Cholesterols and derivatives |
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| Alternative Parents | |
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| Substituents | - Cholesterol-skeleton
- Cholesterol
- Hydroxysteroid
- 3-hydroxysteroid
- 3-hydroxy-delta-5-steroid
- Delta-5-steroid
- Cyclic alcohol
- Secondary alcohol
- Organic oxygen compound
- Hydrocarbon derivative
- Organooxygen compound
- Alcohol
- Aliphatic homopolycyclic compound
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| Molecular Framework | Aliphatic homopolycyclic compounds |
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| External Descriptors | |
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| Ontology |
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| Ontology | No ontology term |
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| Physico-Chemical Properties - Experimental |
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| Physico-Chemical Properties - Experimental | | Property | Value | Reference |
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| Physical state | Solid | |
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| Physical Description | Not Available | |
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| Mass Composition | C 83.87%; H 11.99%; O 4.14% | DFC |
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| Melting Point | Mp 148.5° (anhyd.) | DFC |
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| Boiling Point | Not Available | |
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| Experimental Water Solubility | 9.5e-05 mg/mL at 30 oC | YALKOWSKY,SH & DANNENFELSER,RM (1992) |
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| Experimental logP | Not Available | |
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| Experimental pKa | Not Available | |
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| Isoelectric point | Not Available | |
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| Charge | 0 | |
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| Optical Rotation | [a]D -31.12 (Et2O) | DFC |
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| Spectroscopic UV Data | Not Available | |
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| Density | Not Available | |
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| Refractive Index | Not Available | |
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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 | Cholesterol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-05i3-1109000000-8cd386b595bd5151c5a2 | Spectrum | | Predicted GC-MS | Cholesterol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | | Predicted GC-MS | Cholesterol, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | | Predicted GC-MS | Cholesterol, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
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| MS/MS | | Type | Description | Splash Key | View |
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| MS/MS | LC-MS/MS Spectrum - 20V, Positive | splash10-001i-0019000000-d33ae2f09b3745af19f7 | 2021-09-20 | View Spectrum | | MS/MS | LC-MS/MS Spectrum - 10V, Positive | splash10-000i-0009000000-72e1e0e68254f54a7d16 | 2021-09-20 | View Spectrum | | MS/MS | LC-MS/MS Spectrum - 20V, Positive | splash10-001i-0019000000-0e6567113259722feed3 | 2021-09-20 | View Spectrum | | MS/MS | LC-MS/MS Spectrum - 10V, Positive | splash10-000i-0009000000-cb8a3e161331e32a91dc | 2021-09-20 | View Spectrum | | MS/MS | LC-MS/MS Spectrum - 30V, Positive | splash10-004i-2921000000-a50ff187be4c4b0dbc47 | 2021-09-20 | View Spectrum | | MS/MS | LC-MS/MS Spectrum - 40V, Positive | splash10-004i-3900000000-774698511917a2f1677d | 2021-09-20 | View Spectrum | | MS/MS | LC-MS/MS Spectrum - 50V, Positive | splash10-004i-7900000000-9f3cf4c8537138a6a938 | 2021-09-20 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-014r-0009000000-91a2d07a2ae578ce1331 | 2015-05-26 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-05p9-3139000000-fefcd46ea3ac49633e6c | 2015-05-26 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0c00-5159000000-84415da5c4b1353f88d7 | 2015-05-26 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-000i-0009000000-57deba99fbfb399fdaa9 | 2015-05-27 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-000i-0009000000-92b195d86bf5a087667f | 2015-05-27 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0ldi-2009000000-59339acd74eacce981fd | 2015-05-27 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-000i-0009000000-2bec7ebe240c2c5c3891 | 2021-10-12 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-052o-9145000000-82b357f48da1994eb33b | 2021-10-12 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0a4l-8900000000-b5bc4edeca8f31108fe8 | 2021-10-12 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-000i-0009000000-c037f2d2f217e99b79ac | 2021-10-12 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-000i-0009000000-c037f2d2f217e99b79ac | 2021-10-12 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-000i-0009000000-0664c410862db937f7d6 | 2021-10-12 | View Spectrum |
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| NMR | Not Available |
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| External Links |
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| ChemSpider ID | 9200676 |
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| ChEMBL ID | CHEMBL1867358 |
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| KEGG Compound ID | C00187 |
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| Pubchem Compound ID | 11025495 |
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| Pubchem Substance ID | Not Available |
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| ChEBI ID | 16113 |
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| Phenol-Explorer ID | Not Available |
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| DrugBank ID | DB04540 |
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| HMDB ID | HMDB00067 |
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| CRC / DFC (Dictionary of Food Compounds) ID | HKC02-A:HQO24-G |
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| EAFUS ID | Not Available |
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| Dr. Duke ID | CHOLESTEROL |
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| BIGG ID | 34183 |
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| KNApSAcK ID | C00003648 |
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| HET ID | 1LRI |
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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 | Cholesterol |
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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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| Food | Content Range | Average | Reference |
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| Food | | | Reference |
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| Biological Effects and Interactions |
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| Health Effects / Bioactivities | | Descriptor | ID | Definition | Reference |
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| antioxidant | 22586 | A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324. | DUKE |
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| Enzymes | | Name | Gene Name | UniProt ID |
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| Lysosomal acid lipase/cholesteryl ester hydrolase | LIPA | P38571 | | Apolipoprotein A-I | APOA1 | P02647 | | Sulfotransferase family cytosolic 2B member 1 | SULT2B1 | O00204 | | 7-dehydrocholesterol reductase | DHCR7 | Q9UBM7 | | Sterol O-acyltransferase 1 | SOAT1 | P35610 | | Phosphatidylcholine-sterol acyltransferase | LCAT | P04180 | | Sterol O-acyltransferase 2 | SOAT2 | O75908 | | Nuclear receptor ROR-alpha | RORA | P35398 |
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| Pathways | |
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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 | — Saxholt, E., et al. 'Danish food composition databank, revision 7.' Department of Nutrition, National Food Institute, Technical University of Denmark (2008).
— U.S. Department of Agriculture, Agricultural Research Service. 2008. USDA National Nutrient Database for Standard Reference, Release 21. Nutrient Data Laboratory Home Page.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
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