| Record Information |
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| Version | 1.0 |
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| Creation date | 2010-04-08 22:10:03 UTC |
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| Update date | 2019-11-26 03:06:25 UTC |
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| Primary ID | FDB012221 |
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| Secondary Accession Numbers | Not Available |
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| Chemical Information |
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| FooDB Name | Genistin |
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| Description | Genistin belongs to the class of organic compounds known as isoflavonoid o-glycosides. These are o-glycosylated derivatives of isoflavonoids, which are natural products derived from 3-phenylchromen-4-one. Genistin is a bitter tasting compound. Genistin is found, on average, in the highest concentration within a few different foods, such as soy beans (Glycine max), yogurt, and soy yogurt and in a lower concentration in tofu, soy milk, and soy sauce. Genistin has also been detected, but not quantified in, several different foods, such as oregon yampahs (Perideridia oregana), radishes (Raphanus sativus), italian sweet red peppers (Capsicum annuum), kohlrabis (Brassica oleracea var. gongylodes), and sacred lotus (Nelumbo nucifera). This could make genistin a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Genistin. |
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| CAS Number | 529-59-9 |
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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 | C21H20O10 |
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| IUPAC name | 5-hydroxy-3-(4-hydroxyphenyl)-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-chromen-4-one |
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| InChI Identifier | InChI=1S/C21H20O10/c22-7-15-18(26)19(27)20(28)21(31-15)30-11-5-13(24)16-14(6-11)29-8-12(17(16)25)9-1-3-10(23)4-2-9/h1-6,8,15,18-24,26-28H,7H2 |
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| InChI Key | ZCOLJUOHXJRHDI-UHFFFAOYSA-N |
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| Isomeric SMILES | OCC1OC(OC2=CC(O)=C3C(=O)C(=COC3=C2)C2=CC=C(O)C=C2)C(O)C(O)C1O |
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| Average Molecular Weight | 432.3775 |
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| Monoisotopic Molecular Weight | 432.10564686 |
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| Classification |
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| Description | Belongs to the class of organic compounds known as isoflavonoid o-glycosides. These are o-glycosylated derivatives of isoflavonoids, which are natural products derived from 3-phenylchromen-4-one. |
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| Kingdom | Organic compounds |
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| Super Class | Phenylpropanoids and polyketides |
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| Class | Isoflavonoids |
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| Sub Class | Isoflavonoid O-glycosides |
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| Direct Parent | Isoflavonoid O-glycosides |
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| Alternative Parents | |
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| Substituents | - Isoflavonoid-7-o-glycoside
- Isoflavonoid o-glycoside
- Isoflavone
- Hydroxyisoflavonoid
- Phenolic glycoside
- Hexose monosaccharide
- O-glycosyl compound
- Glycosyl compound
- Chromone
- Benzopyran
- 1-benzopyran
- Pyranone
- 1-hydroxy-2-unsubstituted benzenoid
- Phenol
- 1-hydroxy-4-unsubstituted benzenoid
- Benzenoid
- Pyran
- Monocyclic benzene moiety
- Oxane
- Monosaccharide
- Vinylogous acid
- Heteroaromatic compound
- Secondary alcohol
- Acetal
- Oxacycle
- Organoheterocyclic compound
- Polyol
- Alcohol
- Hydrocarbon derivative
- Organic oxide
- Primary alcohol
- Organic oxygen compound
- Organooxygen compound
- Aromatic heteropolycyclic compound
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| Molecular Framework | Aromatic heteropolycyclic compounds |
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| External Descriptors | - an isoflavone-7-O-β-D-glucoside (CPD-3421 )
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| Ontology |
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| Disposition | Route of exposure: Source: Biological location: |
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| Role | Biological role: |
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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 | Not Available | |
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| Physical Description | Not Available | |
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| Mass Composition | C 58.34%; H 4.66%; O 37.00% | DFC |
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| Melting Point | Mp 254-256° 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]21D -27.7 (MeOH aq.) | DFC |
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| Spectroscopic UV Data | [neutral] lmax 262 () (MeOH) (Berdy) | DFC |
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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 | Genistin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0h9r-8914800000-b5711d35ff3a85cfffae | Spectrum | | Predicted GC-MS | Genistin, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-001r-3620009000-a32e57795ebbf7519666 | Spectrum | | Predicted GC-MS | Genistin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | | Predicted GC-MS | Genistin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | | Predicted GC-MS | Genistin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | | Predicted GC-MS | Genistin, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | | Predicted GC-MS | Genistin, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | | Predicted GC-MS | Genistin, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | | Predicted GC-MS | Genistin, TMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | | Predicted GC-MS | Genistin, TMS_1_5, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | | Predicted GC-MS | Genistin, TMS_1_6, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | | Predicted GC-MS | Genistin, TMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | | Predicted GC-MS | Genistin, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | | Predicted GC-MS | Genistin, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | | Predicted GC-MS | Genistin, TMS_2_4, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | | Predicted GC-MS | Genistin, TMS_2_5, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | | Predicted GC-MS | Genistin, TMS_2_6, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | | Predicted GC-MS | Genistin, TMS_2_7, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | | Predicted GC-MS | Genistin, TMS_2_8, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | | Predicted GC-MS | Genistin, TMS_2_9, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | | Predicted GC-MS | Genistin, TMS_2_10, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | | Predicted GC-MS | Genistin, TMS_2_11, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | | Predicted GC-MS | Genistin, TMS_2_12, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | | Predicted GC-MS | Genistin, TMS_2_13, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | | Predicted GC-MS | Genistin, TMS_2_14, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | 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 | splash10-00e9-0190800000-9dd0f3e25b5de14320cc | 2015-04-24 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-00di-0090000000-7ac795a53e2622d6fa04 | 2015-04-24 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0ukc-2190000000-c75c9f5db7ba30e7d39b | 2015-04-24 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-00lr-0151900000-5143ebb19841b93ba06f | 2015-04-25 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-014i-1090200000-48a472ce7e9a2884d653 | 2015-04-25 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-014i-3290000000-caa3fe4a15ea8a74bf71 | 2015-04-25 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0089-0040900000-91a62edfcb3c87f349ab | 2021-09-25 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-00di-0092000000-22da7f56fe38feb458c7 | 2021-09-25 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-00di-7191100000-a18bd89cece2e53f5e43 | 2021-09-25 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0159-0090500000-ddbc4c7d51cf83124075 | 2021-09-25 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-014i-2090200000-29eb4086be0938317cc7 | 2021-09-25 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-004i-0190000000-fd54ace97f242d3aa505 | 2021-09-25 | View Spectrum |
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| NMR | Not Available |
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| External Links |
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| ChemSpider ID | 4447683 |
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| ChEMBL ID | Not Available |
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| KEGG Compound ID | C09126 |
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| Pubchem Compound ID | 5284639 |
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| Pubchem Substance ID | Not Available |
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| ChEBI ID | 27514 |
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| Phenol-Explorer ID | 404 |
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| DrugBank ID | Not Available |
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| HMDB ID | HMDB33988 |
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| CRC / DFC (Dictionary of Food Compounds) ID | GZR02-N:HFF90-F |
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| EAFUS ID | Not Available |
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| Dr. Duke ID | GENISTIN |
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| BIGG ID | Not Available |
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| KNApSAcK ID | C00002528 |
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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 | Genistein_7-glucoside |
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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 | | estrogenic | | | DUKE | | fungicide | 24127 | A substance used to destroy fungal pests. | DUKE |
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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 | | Flavor | Citations |
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| bitter |
- Ayana Wiener, Marina Shudler, Anat Levit, Masha Y. Niv. BitterDB: a database of bitter compounds. Nucleic Acids Res 2012, 40(Database issue):D413-419. DOI:10.1093/nar/gkr755
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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 | — 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.
— 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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