Record Information |
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Version | 2.0 |
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Created at | 2022-09-07 22:18:09 UTC |
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Updated at | 2022-09-07 22:18:10 UTC |
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NP-MRD ID | NP0257233 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | 2,3,4,5-tetrahydroxy-8-[(2r,3r)-3,5,7-trihydroxy-3,4-dihydro-2h-1-benzopyran-2-yl]benzo[7]annulen-6-one |
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Description | Epitheaflagallin belongs to the class of organic compounds known as 1-benzopyrans. These are organic aromatic compounds that 1-benzopyran, a bicyclic compound made up of a benzene ring fused to a pyran, so that the oxygen atom is at the 1-position. 2,3,4,5-tetrahydroxy-8-[(2r,3r)-3,5,7-trihydroxy-3,4-dihydro-2h-1-benzopyran-2-yl]benzo[7]annulen-6-one is found in Camellia sinensis. It was first documented in 2003 (PMID: 12951464). Based on a literature review a small amount of articles have been published on Epitheaflagallin (PMID: 29131612) (PMID: 26672458) (PMID: 29124233) (PMID: 25307624). |
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Structure | O[C@@H]1CC2=C(O)C=C(O)C=C2O[C@@H]1C1=CC(=O)C(O)=C2C(O)=C(O)C(O)=CC2=C1 InChI=1S/C20H16O9/c21-9-4-11(22)10-6-14(25)20(29-15(10)5-9)8-1-7-2-13(24)18(27)19(28)16(7)17(26)12(23)3-8/h1-5,14,20-22,24-25,27-28H,6H2,(H,23,26)/t14-,20-/m1/s1 |
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Synonyms | Not Available |
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Chemical Formula | C20H16O9 |
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Average Mass | 400.3390 Da |
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Monoisotopic Mass | 400.07943 Da |
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IUPAC Name | 2,3,4,5-tetrahydroxy-8-[(2R,3R)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-2-yl]-6H-benzo[7]annulen-6-one |
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Traditional Name | 2,3,4,5-tetrahydroxy-8-[(2R,3R)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-2-yl]benzo[7]annulen-6-one |
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CAS Registry Number | Not Available |
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SMILES | O[C@@H]1CC2=C(O)C=C(O)C=C2O[C@@H]1C1=CC(=O)C(O)=C2C(O)=C(O)C(O)=CC2=C1 |
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InChI Identifier | InChI=1S/C20H16O9/c21-9-4-11(22)10-6-14(25)20(29-15(10)5-9)8-1-7-2-13(24)18(27)19(28)16(7)17(26)12(23)3-8/h1-5,14,20-22,24-25,27-28H,6H2,(H,23,26)/t14-,20-/m1/s1 |
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InChI Key | KOXRJHMEFYNYME-JLTOFOAXSA-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 1-benzopyrans. These are organic aromatic compounds that 1-benzopyran, a bicyclic compound made up of a benzene ring fused to a pyran, so that the oxygen atom is at the 1-position. |
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Kingdom | Organic compounds |
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Super Class | Organoheterocyclic compounds |
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Class | Benzopyrans |
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Sub Class | 1-benzopyrans |
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Direct Parent | 1-benzopyrans |
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Alternative Parents | |
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Substituents | - 1-benzopyran
- Tropolone
- Tropone
- 1-hydroxy-4-unsubstituted benzenoid
- 1-hydroxy-2-unsubstituted benzenoid
- Alkyl aryl ether
- Phenol
- Benzenoid
- Secondary alcohol
- Cyclic ketone
- Ether
- Polyol
- Oxacycle
- Organic oxide
- Organooxygen compound
- Alcohol
- Organic oxygen compound
- Hydrocarbon derivative
- Aromatic heteropolycyclic compound
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Molecular Framework | Aromatic heteropolycyclic compounds |
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External Descriptors | Not Available |
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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 | - Itoh N, Kurokawa J, Isogai Y, Ogasawara M, Matsunaga T, Okubo T, Katsube Y: Functional Characterization of Epitheaflagallin 3-O-Gallate Generated in Laccase-Treated Green Tea Extracts in the Presence of Gallic Acid. J Agric Food Chem. 2017 Dec 6;65(48):10473-10481. doi: 10.1021/acs.jafc.7b04208. Epub 2017 Nov 27. [PubMed:29131612 ]
- Itoh N, Takagi S, Miki A, Kurokawa J: Characterization and cloning of laccase gene from Hericium coralloides NBRC 7716 suitable for production of epitheaflagallin 3-O-gallate. Enzyme Microb Technol. 2016 Jan;82:125-132. doi: 10.1016/j.enzmictec.2015.09.004. Epub 2015 Sep 14. [PubMed:26672458 ]
- Oku N, Matsukawa M, Yamakawa S, Asai T, Yahara S, Hashimoto F, Akizawa T: Inhibitory effect of green tea polyphenols on membrane-type 1 matrix metalloproteinase, MT1-MMP. Biol Pharm Bull. 2003 Sep;26(9):1235-8. doi: 10.1248/bpb.26.1235. [PubMed:12951464 ]
- Kayashima Y, Murata S, Sato M, Matsuura K, Asanuma T, Chimoto J, Ishii T, Mochizuki K, Kumazawa S, Nakayama T, Yamakawa-Kobayashi K: Tea polyphenols ameliorate fat storage induced by high-fat diet in Drosophila melanogaster. Biochem Biophys Rep. 2015 Oct 30;4:417-424. doi: 10.1016/j.bbrep.2015.10.013. eCollection 2015 Dec. [PubMed:29124233 ]
- Shimamura Y, Aoki N, Sugiyama Y, Nakayama T, Masuda S: Screening of tea extract and theaflavins for inhibitory effects on the biological activity and production of staphylococcal enterotoxin A. J Food Sci. 2014 Nov;79(11):M2294-300. doi: 10.1111/1750-3841.12566. Epub 2014 Oct 11. [PubMed:25307624 ]
- LOTUS database [Link]
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