Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:05:27 UTC |
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Update date | 2020-02-24 19:10:35 UTC |
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Primary ID | FDB002630 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | Vicenin 2 |
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Description | Vicenin 2, also known as vicenin II, belongs to the class of organic compounds known as flavonoid 8-c-glycosides. Flavonoid 8-C-glycosides are compounds containing a carbohydrate moiety which is C-glycosidically linked to 8-position of a 2-phenylchromen-4-one flavonoid backbone. Vicenin 2 is found, on average, in the highest concentration within sweet oranges (Citrus sinensis). Vicenin 2 has also been detected, but not quantified in, several different foods, such as soy beans (Glycine max), tartary buckwheats (Fagopyrum tataricum), amaranths (Amaranthus), spelts (Triticum spelta), and oriental wheats (Triticum turanicum). This could make vicenin 2 a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Vicenin 2. |
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CAS Number | 23666-13-9 |
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Structure | |
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Synonyms | Synonym | Source |
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Apigenin-6,8-di-C-glycopyranoside | MeSH | Vicenin-2 | MeSH | Vicenin II | MeSH | 5,7,4'-Trihydroxyflavone-6,8-di-C-glucoside | HMDB | 6,8-Di-b-D-glucopyranosyl-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one, 9ci | HMDB | 6,8-Di-C-glucopyranosylapigenin | HMDB | 6,8-Di-C-glucosyl-4',5,7-trihydroxyflavone | HMDB | 6,8-Di-C-glucosylapigenin | HMDB | Apigenin 6,8-di-C-glucoside | HMDB | Vicenin-1 | MeSH | 6-C-beta-D-Xylopyranosyl-8-C-beta-D-glucopyranosyl apigenin | MeSH | Vicenin | MeSH | 6,8-Di-b-D-glucopyranosyl-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one, 9CI | db_source |
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Predicted Properties | |
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Chemical Formula | C27H30O15 |
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IUPAC name | 5,7-dihydroxy-2-(4-hydroxyphenyl)-6,8-bis[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-4H-chromen-4-one |
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InChI Identifier | InChI=1S/C27H30O15/c28-6-12-17(32)21(36)23(38)26(41-12)15-19(34)14-10(31)5-11(8-1-3-9(30)4-2-8)40-25(14)16(20(15)35)27-24(39)22(37)18(33)13(7-29)42-27/h1-5,12-13,17-18,21-24,26-30,32-39H,6-7H2 |
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InChI Key | FIAAVMJLAGNUKW-UHFFFAOYSA-N |
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Isomeric SMILES | OCC1OC(C(O)C(O)C1O)C1=C(O)C(C2OC(CO)C(O)C(O)C2O)=C2OC(=CC(=O)C2=C1O)C1=CC=C(O)C=C1 |
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Average Molecular Weight | 594.5181 |
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Monoisotopic Molecular Weight | 594.15847029 |
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Classification |
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Description | Belongs to the class of organic compounds known as flavonoid 8-c-glycosides. Flavonoid 8-C-glycosides are compounds containing a carbohydrate moiety which is C-glycosidically linked to 8-position of a 2-phenylchromen-4-one flavonoid backbone. |
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Kingdom | Organic compounds |
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Super Class | Phenylpropanoids and polyketides |
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Class | Flavonoids |
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Sub Class | Flavonoid glycosides |
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Direct Parent | Flavonoid 8-C-glycosides |
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Alternative Parents | |
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Substituents | - Flavonoid-8-c-glycoside
- Hydroxyflavonoid
- 4'-hydroxyflavonoid
- 5-hydroxyflavonoid
- 7-hydroxyflavonoid
- Flavone
- Phenolic glycoside
- Hexose monosaccharide
- Glycosyl compound
- C-glycosyl compound
- Chromone
- 1-benzopyran
- Benzopyran
- Pyranone
- Phenol
- 1-hydroxy-2-unsubstituted benzenoid
- Pyran
- Monosaccharide
- Monocyclic benzene moiety
- Benzenoid
- Oxane
- Heteroaromatic compound
- Vinylogous acid
- Secondary alcohol
- Ether
- Dialkyl ether
- Organoheterocyclic compound
- Oxacycle
- Polyol
- Primary alcohol
- Organic oxide
- Organic oxygen compound
- Alcohol
- Hydrocarbon derivative
- Organooxygen compound
- Aromatic heteropolycyclic compound
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Molecular Framework | Aromatic heteropolycyclic compounds |
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External Descriptors | Not Available |
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Ontology |
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Disposition | Route of exposure: Source: Biological location: |
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Physico-Chemical Properties |
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Physico-Chemical Properties - Experimental | Property | Value | Reference |
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Physical state | Not Available | |
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Physical Description | Not Available | |
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Mass Composition | C 54.55%; H 5.09%; O 40.37% | DFC |
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Melting Point | Mp 233-236° (214-216° dec.) | DFC |
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Boiling Point | Not Available | |
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Experimental Water Solubility | Not Available | |
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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 | Not Available | |
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Optical Rotation | [a]D +71 (c, 0.36 in H2O) | 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 | Vicenin 2, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0w59-0000390000-4715bf8584b5737232b4 | Spectrum | Predicted GC-MS | Vicenin 2, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0571-2300179000-2bd75622b8a0edf7d54f | Spectrum | Predicted GC-MS | Vicenin 2, "Vicenin 2,1TMS,#1" TMS, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Vicenin 2, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Vicenin 2, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Vicenin 2, TMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Vicenin 2, TMS_1_5, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Vicenin 2, TMS_1_6, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Vicenin 2, TMS_1_7, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Vicenin 2, TMS_1_8, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Vicenin 2, TMS_1_9, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Vicenin 2, TMS_1_10, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Vicenin 2, TMS_1_11, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Vicenin 2, TMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Vicenin 2, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Vicenin 2, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Vicenin 2, TMS_2_4, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Vicenin 2, TMS_2_5, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Vicenin 2, TMS_2_6, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Vicenin 2, TMS_2_7, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Vicenin 2, TMS_2_8, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Vicenin 2, TMS_2_9, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Vicenin 2, TMS_2_10, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Vicenin 2, TMS_2_11, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Vicenin 2, TMS_2_12, 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 - , negative | splash10-0006-0005290000-9a78bec3e031b476b983 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - , negative | splash10-0006-0094770000-4a713c915b058c32b42c | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - , negative | splash10-01ox-0052950000-b3d4ef3891bc5396575c | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - , positive | splash10-056r-0029730000-195463720c0564fc0e41 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - , positive | splash10-01q9-0049410000-b9e46e9b61fd04b1fd54 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 6V, Positive | splash10-0006-0005190000-c3bc69d503efe086b104 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 6V, Positive | splash10-002b-0159000000-73201d25ff9bd498fbbc | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 6V, Positive | splash10-0002-0006590000-0b790319282d96c7f1b2 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 6V, Positive | splash10-0002-0294000000-c48ccbabbc82b2e70436 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 6V, Positive | splash10-004i-0009810000-02776207343f58da4e29 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 6V, Positive | splash10-0570-0009710000-467ea3b5a1fccdb37cb6 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 6V, Positive | splash10-0ue9-0009100000-3c3c2fcb4c9126028467 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 6V, Positive | splash10-002b-0005690000-6661389fc4db228fec6b | 2021-09-20 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-002b-0000190000-48ccaded9e493aef6078 | 2015-04-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-06vj-1200390000-d10e5bb5b26e0eefb0f7 | 2015-04-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0550-1007940000-a8fcd22df6cf3cfc5458 | 2015-04-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-002b-0000190000-48ccaded9e493aef6078 | 2015-04-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-06vj-1200390000-d10e5bb5b26e0eefb0f7 | 2015-04-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0550-1007940000-a8fcd22df6cf3cfc5458 | 2015-04-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0006-0000390000-d59360ecaa9a1208b0d4 | 2015-04-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-00fu-3100690000-9b42c7acc566ef75a9f7 | 2015-04-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0f7c-7306960000-804c13a60653afea62e1 | 2015-04-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0006-0000390000-d59360ecaa9a1208b0d4 | 2015-04-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-00fu-3100690000-9b42c7acc566ef75a9f7 | 2015-04-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0f7c-7306960000-804c13a60653afea62e1 | 2015-04-25 | View Spectrum |
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NMR | Not Available |
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External Links |
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ChemSpider ID | 2341472 |
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ChEMBL ID | Not Available |
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KEGG Compound ID | C10195 |
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Pubchem Compound ID | 3084407 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | Not Available |
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Phenol-Explorer ID | 247 |
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DrugBank ID | Not Available |
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HMDB ID | HMDB30708 |
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CRC / DFC (Dictionary of Food Compounds) ID | CMT14-X:CMT14-X |
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EAFUS ID | Not Available |
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Dr. Duke ID | VICENIN-2|APIGENIN-6,8-DI-C-GLUCOSIDE |
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BIGG ID | Not Available |
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KNApSAcK ID | C00006229 |
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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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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 | |
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Enzymes | Not Available |
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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 | Not Available |
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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 | — 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. — Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.
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