Record Information |
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Version | 1.0 |
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Created at | 2022-06-29 17:35:56 UTC |
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Updated at | 2022-06-29 17:35:56 UTC |
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NP-MRD ID | NP0138576 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | Vestitol |
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Description | (-)-Vestitol belongs to the class of organic compounds known as 4'-o-methylated isoflavonoids. These are isoflavonoids with methoxy groups attached to the C4' atom of the isoflavonoid backbone. Isoflavonoids are natural products derived from 3-phenylchromen-4-one (-)-vestitol is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, (-)-vestitol has been detected, but not quantified in, several different foods, such as pineapples, grapefruit/pummelo hybrids, common beets, pitanga, and orange bell peppers. Vestitol is found in Centrolobium tomentosum, Dalbergia odorifera, Dalbergia sissoo, Endosamara racemosa, Gliricidia sepium, Glycyrrhiza glabra, Glycyrrhiza pallidiflora, Glycyrrhiza uralensis, Hedysarum polybotrys, Hedysarum theinum, Lotus angustissimus, Lotus corniculatus, Maackia amurensis, Medicago rugosa, Vigna angularis and Wisteria brachybotrys. It was first documented in 1982 (PMID: 17396779). This could make (-)-vestitol a potential biomarker for the consumption of these foods (PMID: 22074222) (PMID: 20699571) (PMID: 21502738) (PMID: 23607483). |
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Structure | COC1=CC(O)=C(C=C1)C1COC2=C(C1)C=CC(O)=C2 InChI=1S/C16H16O4/c1-19-13-4-5-14(15(18)8-13)11-6-10-2-3-12(17)7-16(10)20-9-11/h2-5,7-8,11,17-18H,6,9H2,1H3 |
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Synonyms | Not Available |
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Chemical Formula | C16H16O4 |
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Average Mass | 272.3000 Da |
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Monoisotopic Mass | 272.10486 Da |
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IUPAC Name | 3-(2-hydroxy-4-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-7-ol |
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Traditional Name | 3-(2-hydroxy-4-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-7-ol |
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CAS Registry Number | 35878-41-2 |
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SMILES | COC1=CC(O)=C(C=C1)C1COC2=C(C1)C=CC(O)=C2 |
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InChI Identifier | InChI=1S/C16H16O4/c1-19-13-4-5-14(15(18)8-13)11-6-10-2-3-12(17)7-16(10)20-9-11/h2-5,7-8,11,17-18H,6,9H2,1H3 |
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InChI Key | XRVFNNUXNVWYTI-UHFFFAOYSA-N |
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Experimental Spectra |
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| Not Available | Predicted Spectra |
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| Spectrum Type | Description | Depositor ID | Depositor Organization | Depositor | Deposition Date | View |
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1D NMR | 13C NMR Spectrum (1D, 25 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 252 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 50 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 75 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 101 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 126 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 151 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 176 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 201 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 226 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| Chemical Shift Submissions |
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| Not Available | Species |
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Species of Origin | |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as 4'-o-methylated isoflavonoids. These are isoflavonoids with methoxy groups attached to the C4' atom of the isoflavonoid backbone. Isoflavonoids 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 | O-methylated isoflavonoids |
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Direct Parent | 4'-O-methylated isoflavonoids |
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Alternative Parents | |
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Substituents | - 4p-methoxyisoflavonoid
- Isoflavanol
- Hydroxyisoflavonoid
- Isoflavan
- Chromane
- Benzopyran
- Methoxyphenol
- 1-benzopyran
- Phenoxy compound
- Anisole
- Phenol ether
- Methoxybenzene
- Alkyl aryl ether
- 1-hydroxy-2-unsubstituted benzenoid
- 1-hydroxy-4-unsubstituted benzenoid
- Phenol
- Monocyclic benzene moiety
- Benzenoid
- Oxacycle
- Ether
- Organoheterocyclic compound
- Organooxygen compound
- Hydrocarbon derivative
- Organic oxygen compound
- Aromatic heteropolycyclic compound
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Molecular Framework | Aromatic heteropolycyclic compounds |
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External Descriptors | |
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Physical Properties |
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State | Not Available |
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Experimental Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Predicted Properties | |
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General References | - Gafner S, Bergeron C, Villinski JR, Godejohann M, Kessler P, Cardellina JH, Ferreira D, Feghali K, Grenier D: Isoflavonoids and coumarins from Glycyrrhiza uralensis: antibacterial activity against oral pathogens and conversion of isoflavans into isoflavan-quinones during purification. J Nat Prod. 2011 Dec 27;74(12):2514-9. doi: 10.1021/np2004775. Epub 2011 Nov 10. [PubMed:22074222 ]
- Ingham JL: A New isoflavanone phytoalexin from Medicago rugosa. Planta Med. 1982 May;45(5):46-7. doi: 10.1055/s-2007-971240. [PubMed:17396779 ]
- Ueda H, Sugimoto Y: Vestitol as a chemical barrier against intrusion of parasitic plant Striga hermonthica into Lotus japonicus roots. Biosci Biotechnol Biochem. 2010;74(8):1662-7. doi: 10.1271/bbb.100285. Epub 2010 Aug 7. [PubMed:20699571 ]
- Masunaka A, Hyakumachi M, Takenaka S: Plant growth-promoting fungus, Trichoderma koningi suppresses isoflavonoid phytoalexin vestitol production for colonization on/in the roots of Lotus japonicus. Microbes Environ. 2011;26(2):128-34. doi: 10.1264/jsme2.me10176. Epub 2011 Feb 26. [PubMed:21502738 ]
- Bueno-Silva B, Alencar SM, Koo H, Ikegaki M, Silva GV, Napimoga MH, Rosalen PL: Anti-inflammatory and antimicrobial evaluation of neovestitol and vestitol isolated from Brazilian red propolis. J Agric Food Chem. 2013 May 15;61(19):4546-50. doi: 10.1021/jf305468f. Epub 2013 May 3. [PubMed:23607483 ]
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