Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2012-09-11 19:53:02 UTC |
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Update Date | 2022-07-19 22:09:52 UTC |
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HMDB ID | HMDB0034950 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Rebaudioside A |
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Description | Rebaudioside A belongs to the class of organic compounds known as steviol glycosides. These are prenol lipids containing a carbohydrate moiety glycosidically linked to a steviol (a diterpenoid based on a 13-hydroxykaur-16-en-18-oic acid) moiety. Steviol glycosides are the chemical compounds responsible for the sweet taste of the leaves of the South American plant Stevia rebaudiana (Asteraceae), which is a member of the sunflower family native to Paraguay and Brazil. Steviol glycosides are the main ingredients (or precursors) of many sweeteners marketed under the generic name stevia and several other trade names. Stevia is widely used as a non-nutritive replacement for common sugar (sucrose). Rebaudioside A is one of the major sweetening constituents of commercial stevia. Stevia leaves typically contain 9.1% stevioside and 3.8% rebaudioside A (by dry weight) as the two major sweeteners (PMID: 19961353 ). Rebaudioside A is the sweetest and most stable steviol glycoside. Rebaudioside A was first isolated by two French chemists (Bridel and Lavielle) in 1931. A recent evaluation found rebaudoside A to be about 240 times sweeter, and stevioside about 140 times sweeter than sucrose (PMID: 17397883 ). Rebaudioside A also had the least bitterness and aftertaste of all steviol glycosides (PMID: 19961353 ). Rebaudioside A binds to the T1R2 and T1R3 (sweet) receptors as well as the T2R4 and T2R14 (bitter) receptors (PMID: 24705770 ). Rebaudioside A is not an endogenously occurring human metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Rebaudioside A is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults or impacts from environmental, dietary and occupational sources. |
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Structure | [H][C@]1(O)[C@]([H])(O)[C@@]([H])(CO)O[C@@]([H])(OC(=O)[C@]2(C)CCC[C@@]3(C)[C@]4([H])CC[C@@]5(C[C@]4(CC5=C)CC[C@]23[H])O[C@]2([H])O[C@]([H])(CO)[C@@]([H])(O)[C@]([H])(O[C@]3([H])O[C@]([H])(CO)[C@@]([H])(O)[C@]([H])(O)[C@@]3([H])O)[C@@]2([H])O[C@]2([H])O[C@]([H])(CO)[C@@]([H])(O)[C@]([H])(O)[C@@]2([H])O)[C@]1([H])O InChI=1S/C44H70O23/c1-17-11-43-9-5-22-41(2,7-4-8-42(22,3)40(59)66-38-33(58)30(55)26(51)20(14-47)62-38)23(43)6-10-44(17,16-43)67-39-35(65-37-32(57)29(54)25(50)19(13-46)61-37)34(27(52)21(15-48)63-39)64-36-31(56)28(53)24(49)18(12-45)60-36/h18-39,45-58H,1,4-16H2,2-3H3/t18-,19-,20-,21-,22+,23+,24-,25-,26-,27-,28+,29+,30+,31-,32-,33-,34+,35-,36+,37+,38+,39+,41-,42-,43-,44+/m1/s1 |
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Synonyms | Value | Source |
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13-[(2-O-beta-D-Glucopyranosyl-3-O-beta-D-glucopyranosyl-beta-D-glucopyranosyl)oxy]-ent-kaur-16-en-19-Oic acid beta-D-glucopyranosyl ester | ChEBI | 19-O-beta-Glucopyranosyl-13-O-(beta-glucopyranosyl(1-2)-beta-glucopyranosyl(1-3))-beta-glucopyranosyl-13-hydroxykaur-16-en-19-Oic acid | ChEBI | 19-O-beta-Glucopyranosyl-13-O-(beta-glucopyranosyl(1-2)-beta-glucopyranosyl(1-3))-beta-glucopyranosylsteviol | ChEBI | Reb a | ChEBI | Reb-a | ChEBI | Rebaudioside-a | ChEBI | Stevia | ChEBI | Sweetener 4g-S | ChEBI | 13-[(2-O-b-D-Glucopyranosyl-3-O-b-D-glucopyranosyl-b-D-glucopyranosyl)oxy]-ent-kaur-16-en-19-Oate b-D-glucopyranosyl ester | Generator | 13-[(2-O-b-D-Glucopyranosyl-3-O-b-D-glucopyranosyl-b-D-glucopyranosyl)oxy]-ent-kaur-16-en-19-Oic acid b-D-glucopyranosyl ester | Generator | 13-[(2-O-beta-D-Glucopyranosyl-3-O-beta-D-glucopyranosyl-beta-D-glucopyranosyl)oxy]-ent-kaur-16-en-19-Oate beta-D-glucopyranosyl ester | Generator | 13-[(2-O-Β-D-glucopyranosyl-3-O-β-D-glucopyranosyl-β-D-glucopyranosyl)oxy]-ent-kaur-16-en-19-Oate β-D-glucopyranosyl ester | Generator | 13-[(2-O-Β-D-glucopyranosyl-3-O-β-D-glucopyranosyl-β-D-glucopyranosyl)oxy]-ent-kaur-16-en-19-Oic acid β-D-glucopyranosyl ester | Generator | 19-O-b-Glucopyranosyl-13-O-(b-glucopyranosyl(1-2)-b-glucopyranosyl(1-3))-b-glucopyranosyl-13-hydroxykaur-16-en-19-Oate | Generator | 19-O-b-Glucopyranosyl-13-O-(b-glucopyranosyl(1-2)-b-glucopyranosyl(1-3))-b-glucopyranosyl-13-hydroxykaur-16-en-19-Oic acid | Generator | 19-O-beta-Glucopyranosyl-13-O-(beta-glucopyranosyl(1-2)-beta-glucopyranosyl(1-3))-beta-glucopyranosyl-13-hydroxykaur-16-en-19-Oate | Generator | 19-O-Β-glucopyranosyl-13-O-(β-glucopyranosyl(1-2)-β-glucopyranosyl(1-3))-β-glucopyranosyl-13-hydroxykaur-16-en-19-Oate | Generator | 19-O-Β-glucopyranosyl-13-O-(β-glucopyranosyl(1-2)-β-glucopyranosyl(1-3))-β-glucopyranosyl-13-hydroxykaur-16-en-19-Oic acid | Generator | 19-O-b-Glucopyranosyl-13-O-(b-glucopyranosyl(1-2)-b-glucopyranosyl(1-3))-b-glucopyranosylsteviol | Generator | 19-O-Β-glucopyranosyl-13-O-(β-glucopyranosyl(1-2)-β-glucopyranosyl(1-3))-β-glucopyranosylsteviol | Generator | (2S,3R,4S,5S,6R)-3,4,5-Trihydroxy-6-(hydroxymethyl)oxan-2-yl (1R,4S,5R,9S,10R,13S)-13-{[(2S,3R,4S,5R,6R)-5-hydroxy-6-(hydroxymethyl)-3,4-bis({[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})oxan-2-yl]oxy}-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylic acid | HMDB | Stevioside a3 | HMDB | Rebaudioside A | MeSH |
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Chemical Formula | C44H70O23 |
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Average Molecular Weight | 967.021 |
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Monoisotopic Molecular Weight | 966.430788514 |
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IUPAC Name | (2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (1R,4S,5R,9S,10R,13S)-13-{[(2S,3R,4S,5R,6R)-5-hydroxy-6-(hydroxymethyl)-3,4-bis({[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})oxan-2-yl]oxy}-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecane-5-carboxylate |
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Traditional Name | (2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (1R,4S,5R,9S,10R,13S)-13-{[(2S,3R,4S,5R,6R)-5-hydroxy-6-(hydroxymethyl)-3,4-bis({[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})oxan-2-yl]oxy}-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecane-5-carboxylate |
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CAS Registry Number | 58543-16-1 |
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SMILES | [H][C@@]1(O[C@H]2[C@H](O)[C@@H](CO)O[C@@H](O[C@@]34C[C@]5(CC3=C)CC[C@]3([H])[C@@](C)(CCC[C@@]3(C)[C@]5([H])CC4)C(=O)O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)[C@@H]2O[C@]2([H])O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O |
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InChI Identifier | InChI=1S/C44H70O23/c1-17-11-43-9-5-22-41(2,7-4-8-42(22,3)40(59)66-38-33(58)30(55)26(51)20(14-47)62-38)23(43)6-10-44(17,16-43)67-39-35(65-37-32(57)29(54)25(50)19(13-46)61-37)34(27(52)21(15-48)63-39)64-36-31(56)28(53)24(49)18(12-45)60-36/h18-39,45-58H,1,4-16H2,2-3H3/t18-,19-,20-,21-,22+,23+,24-,25-,26-,27-,28+,29+,30+,31-,32-,33-,34+,35-,36+,37+,38+,39+,41-,42-,43-,44+/m1/s1 |
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InChI Key | HELXLJCILKEWJH-NCGAPWICSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as steviol glycosides. These are prenol lipids containing a carbohydrate moiety glycosidically linked to a steviol (a diterpenoid based on a 13-Hydroxykaur-16-en-18-oic acid) moiety. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Prenol lipids |
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Sub Class | Terpene glycosides |
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Direct Parent | Steviol glycosides |
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Alternative Parents | |
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Substituents | - Steviol glycoside
- Oligosaccharide
- Diterpenoid
- Kaurane diterpenoid
- Fatty acyl glycoside
- Glycosyl compound
- O-glycosyl compound
- Fatty acyl
- Oxane
- Carboxylic acid ester
- Secondary alcohol
- Oxacycle
- Monocarboxylic acid or derivatives
- Organoheterocyclic compound
- Acetal
- Carboxylic acid derivative
- Polyol
- Organooxygen compound
- Organic oxygen compound
- Organic oxide
- Alcohol
- Hydrocarbon derivative
- Carbonyl group
- Primary alcohol
- Aliphatic heteropolycyclic compound
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Molecular Framework | Aliphatic heteropolycyclic compounds |
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External Descriptors | Not Available |
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Ontology |
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Physiological effect | Not Available |
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Disposition | |
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Process | |
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Role | |
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Physical Properties |
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State | Solid |
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Experimental Molecular Properties | |
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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | | Show more...
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesNot Available | Show more...
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Spectra |
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| MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Experimental LC-MS/MS | LC-MS/MS Spectrum - Rebaudioside A LC-ESI-QQ 20V, negative-QTOF | splash10-0uxr-0000000079-75402eef616f2b12831c | 2020-07-21 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Rebaudioside A LC-ESI-QQ 40V, negative-QTOF | splash10-0udi-0000000090-fb46c72609f54077cf9f | 2020-07-21 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Rebaudioside A LC-ESI-QQ 60V, negative-QTOF | splash10-0udl-0001206090-44ebe132417d2ec16d00 | 2020-07-21 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Rebaudioside A LC-ESI-QQ 80V, negative-QTOF | splash10-00or-0004903000-5f4f5ef5cb14a46c0404 | 2020-07-21 | HMDB team, MONA | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Rebaudioside A 10V, Positive-QTOF | splash10-000i-0003407944-099a80a1866d9d12a98a | 2016-06-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Rebaudioside A 20V, Positive-QTOF | splash10-0016-0105609510-c96697836b2d1aafe2ca | 2016-06-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Rebaudioside A 40V, Positive-QTOF | splash10-0006-0114219321-3f7bdf66df4e62b9d735 | 2016-06-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Rebaudioside A 10V, Negative-QTOF | splash10-0ftk-0301406869-401b87bfebcf28e217d4 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Rebaudioside A 20V, Negative-QTOF | splash10-01tj-0810517978-553fcbc8360b4f975878 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Rebaudioside A 40V, Negative-QTOF | splash10-004i-2912405030-6a11a761d8d227a3bcf9 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Rebaudioside A 10V, Negative-QTOF | splash10-0gb9-0000001269-f47808f99d3ef6acf100 | 2021-09-21 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Rebaudioside A 20V, Negative-QTOF | splash10-0a4i-8300001397-f498c720bf4e6a9aacd1 | 2021-09-21 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Rebaudioside A 40V, Negative-QTOF | splash10-007c-5100009231-030e605dab68d0397f94 | 2021-09-21 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Rebaudioside A 10V, Positive-QTOF | splash10-06rl-0101608955-231c87c74fb5ee2e0ca3 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Rebaudioside A 20V, Positive-QTOF | splash10-0ktf-2627409455-184dd1d1d8afaa68067f | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Rebaudioside A 40V, Positive-QTOF | splash10-0a4i-9803304652-6890556b9fa860d144f5 | 2021-09-25 | Wishart Lab | View Spectrum |
NMR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Predicted 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum |
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Biological Properties |
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Cellular Locations | - Cytoplasm
- Extracellular
- Membrane
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Biospecimen Locations | Not Available |
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Tissue Locations | Not Available |
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Pathways | |
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Normal Concentrations |
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| Not Available |
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Abnormal Concentrations |
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| Not Available |
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Associated Disorders and Diseases |
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Disease References | None |
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Associated OMIM IDs | None |
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External Links |
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DrugBank ID | Not Available |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB013543 |
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KNApSAcK ID | C00023175 |
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Chemspider ID | 5294031 |
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KEGG Compound ID | Not Available |
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BioCyc ID | CPD-14506 |
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BiGG ID | Not Available |
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Wikipedia Link | Rebaudioside_A |
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METLIN ID | Not Available |
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PubChem Compound | 6918840 |
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PDB ID | Not Available |
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ChEBI ID | 145012 |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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MarkerDB ID | Not Available |
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Good Scents ID | rw1600541 |
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References |
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Synthesis Reference | Not Available |
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Material Safety Data Sheet (MSDS) | Not Available |
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General References | - Pilz RB, Willis RC, Boss GR: The influence of ribose 5-phosphate availability on purine synthesis of cultured human lymphoblasts and mitogen-stimulated lymphocytes. J Biol Chem. 1984 Mar 10;259(5):2927-35. [PubMed:6699001 ]
- Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
- Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
- Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
- Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
- Brandle JE, Telmer PG: Steviol glycoside biosynthesis. Phytochemistry. 2007 Jul;68(14):1855-63. doi: 10.1016/j.phytochem.2007.02.010. Epub 2007 Mar 29. [PubMed:17397883 ]
- Risso D, Morini G, Pagani L, Quagliariello A, Giuliani C, De Fanti S, Sazzini M, Luiselli D, Tofanelli S: Genetic signature of differential sensitivity to stevioside in the Italian population. Genes Nutr. 2014 May;9(3):401. doi: 10.1007/s12263-014-0401-y. Epub 2014 Apr 6. [PubMed:24705770 ]
- Goyal SK, Samsher, Goyal RK: Stevia (Stevia rebaudiana) a bio-sweetener: a review. Int J Food Sci Nutr. 2010 Feb;61(1):1-10. doi: 10.3109/09637480903193049. [PubMed:19961353 ]
- (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
- Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.
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