Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:11:43 UTC |
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Update date | 2019-11-26 03:11:18 UTC |
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Primary ID | FDB015221 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | Vitisin A |
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Description | Vitisin A belongs to the class of organic compounds known as biflavonoids and polyflavonoids. These are organic compounds containing at least two flavan/flavone units. These units are usually linked through CC or C-O-C bonds. Some examples include C2-O-C3, C2-O-C4, C3'-C3''', and C6-C8''. Vitisin A is found, on average, in the highest concentration within grape wine. Vitisin A has also been detected, but not quantified in, a few different foods, such as alcoholic beverages, common grapes (Vitis vinifera), and red wine. This could make vitisin a a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Vitisin A. |
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CAS Number | 184362-09-2 |
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Structure | |
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Synonyms | |
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Predicted Properties | |
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Chemical Formula | C26H25O14 |
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IUPAC name | 7-carboxy-11-hydroxy-3-(4-hydroxy-3,5-dimethoxyphenyl)-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2lambda4,8-dioxatricyclo[7.3.1.0^{5,13}]trideca-1(13),2,4,6,9,11-hexaen-2-ylium |
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InChI Identifier | InChI=1S/C26H24O14/c1-35-14-3-9(4-15(36-2)19(14)29)23-24(40-26-22(32)21(31)20(30)17(8-27)39-26)11-7-16(25(33)34)37-12-5-10(28)6-13(38-23)18(11)12/h3-7,17,20-22,26-27,30-32H,8H2,1-2H3,(H2-,28,29,33,34)/p+1/t17-,20-,21+,22-,26+/m1/s1 |
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InChI Key | QVULQDHVHOUFCX-AQFMKAHKSA-O |
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Isomeric SMILES | COC1=CC(=CC(OC)=C1O)C1=[O+]C2=C3C(OC(=CC3=C1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)C(O)=O)=CC(O)=C2 |
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Average Molecular Weight | 561.4683 |
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Monoisotopic Molecular Weight | 561.124430508 |
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Classification |
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Description | Belongs to the class of organic compounds known as biflavonoids and polyflavonoids. These are organic compounds containing at least two flavan/flavone units. These units are usually linked through CC or C-O-C bonds. Some examples include C2-O-C3, C2-O-C4, C3'-C3''', and C6-C8''. |
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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 | Biflavonoids and polyflavonoids |
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Direct Parent | Biflavonoids and polyflavonoids |
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Alternative Parents | |
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Substituents | - Bi- and polyflavonoid skeleton
- Proanthocyanidin
- Anthocyanidin-3-o-glycoside
- Anthocyanin
- Flavonoid o-glycoside
- Flavonoid-3-o-glycoside
- 3p-methoxyflavonoid-skeleton
- 4'-hydroxyflavonoid
- 7-hydroxyflavonoid
- Hydroxyflavonoid
- Anthocyanidin
- Hexose monosaccharide
- Glycosyl compound
- O-glycosyl compound
- Benzopyran
- M-dimethoxybenzene
- Dimethoxybenzene
- Methoxyphenol
- 1-benzopyran
- Phenol ether
- Anisole
- Methoxybenzene
- Phenoxy compound
- Phenol
- Alkyl aryl ether
- 1-hydroxy-2-unsubstituted benzenoid
- Oxane
- Benzenoid
- Monosaccharide
- Monocyclic benzene moiety
- Heteroaromatic compound
- Secondary alcohol
- Polyol
- Monocarboxylic acid or derivatives
- Acetal
- Organoheterocyclic compound
- Ether
- Oxacycle
- Carboxylic acid derivative
- Carboxylic acid
- Hydrocarbon derivative
- Primary alcohol
- Organic oxygen compound
- Alcohol
- Organooxygen compound
- Organic oxide
- Organic cation
- 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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Role | Biological role: |
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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 | Vitisin A, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0abc-9300350000-9a87afcd8c7a911597ad | Spectrum | Predicted GC-MS | Vitisin A, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0avi-9200037000-377e9278f6800932334e | Spectrum | Predicted GC-MS | Vitisin A, "Vitisin A,1TMS,#1" TMS, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Vitisin A, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Vitisin A, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Vitisin A, TMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Vitisin A, TMS_1_5, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Vitisin A, TMS_1_6, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Vitisin A, TMS_1_7, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Vitisin A, TMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Vitisin A, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Vitisin A, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Vitisin A, TMS_2_4, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Vitisin A, TMS_2_5, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Vitisin A, TMS_2_6, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Vitisin A, TMS_2_7, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Vitisin A, TMS_2_8, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Vitisin A, TMS_2_9, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Vitisin A, TMS_2_10, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Vitisin A, TMS_2_11, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Vitisin A, TMS_2_12, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Vitisin A, TMS_2_13, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Vitisin A, TMS_2_14, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Vitisin A, TMS_2_15, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Vitisin A, TMS_2_16, 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 | splash10-03di-0100090000-db62db54a92394f4b01d | 2016-08-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-03dj-1200090000-9b8b3dbfe9cb7d945985 | 2016-08-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-01ow-7902030000-a13b6d39987edfce2a85 | 2016-08-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-03di-2300090000-41f4fa71d6e8862274fc | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-03di-5700090000-4656c50bef5697b84b24 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-002f-9500000000-37349fe117dc8607bc16 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0w2d-0008590000-1bd578101ffdda52fb5f | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0f6t-0009320000-abd37ec220c242d2fd22 | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0002-5309210000-f9feb2c8ca6061dadd65 | 2021-09-22 | View Spectrum |
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NMR | Not Available |
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External Links |
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ChemSpider ID | Not Available |
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ChEMBL ID | Not Available |
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KEGG Compound ID | Not Available |
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Pubchem Compound ID | Not Available |
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Pubchem Substance ID | Not Available |
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ChEBI ID | Not Available |
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Phenol-Explorer ID | 63 |
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DrugBank ID | Not Available |
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HMDB ID | HMDB36348 |
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CRC / DFC (Dictionary of Food Compounds) ID | BOX04-R:JYT18-G |
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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 | C00011186 |
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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 | 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 |
- Fulcrand H, Benabdeljalil C, Rigaud J, Cheynier V, Moutounet M: A new class of wine pigments generated by reaction between pyruvic acid and grape anthocyanins. Phytochemistry. 1998 Apr;47(7):1401-7. Pubmed [Structure]
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Content Reference | — 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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