Record Information |
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Version | 1.0 |
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Created at | 2021-11-12 23:52:47 UTC |
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Updated at | 2024-04-19 09:25:09 UTC |
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NP-MRD ID | NP0044150 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | 6,7,4'-Trihydroxyisoflavone |
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Description | 6-Hydroxydaidzein, also known as demethyltexasin or soybean factor 2, belongs to the class of organic compounds known as isoflavones. These are polycyclic compounds containing a 2-isoflavene skeleton which bears a ketone group at the C4 carbon atom. Thus, 6-hydroxydaidzein is considered to be a flavonoid lipid molecule. 6-Hydroxydaidzein is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, 6-Hydroxydaidzein has been detected, but not quantified in, pulses and soy beans. This could make 6-hydroxydaidzein a potential biomarker for the consumption of these foods. 6,7,4'-Trihydroxyisoflavone is found in Centrosema haitiense, Taxus fuana and Taxus yunnanensis. It was first documented in 1999 (PMID: 10540753). A hydroxyisoflavone that is daidzein bearing an additional hydroxy substituent at position 6 (PMID: 15914921) (PMID: 12784638) (PMID: 15215607) (PMID: 16372328). |
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Structure | OC1=CC=C(C=C1)C1=COC2=CC(O)=C(O)C=C2C1=O InChI=1S/C15H10O5/c16-9-3-1-8(2-4-9)11-7-20-14-6-13(18)12(17)5-10(14)15(11)19/h1-7,16-18H |
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Synonyms | Value | Source |
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6,7,4'-Trihydroxyisoflavone | ChEBI | 6,7-Dihydroxy-3-(4-hydroxy-phenyl)-chromen-4-one | HMDB | 6,7-Dihydroxy-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-one, 9ci | HMDB | 6,7-Dihydroxy-3-(4-hydroxyphenyl)-4H-chromen-4-one | HMDB | Demethyltexasin | HMDB | Soybean factor 2 | HMDB | 6-Hydroxydaidzein | ChEBI |
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Chemical Formula | C15H10O5 |
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Average Mass | 270.2369 Da |
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Monoisotopic Mass | 270.05282 Da |
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IUPAC Name | 6,7-dihydroxy-3-(4-hydroxyphenyl)-4H-chromen-4-one |
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Traditional Name | 6-hydroxydaidzein |
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CAS Registry Number | Not Available |
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SMILES | OC1=CC=C(C=C1)C1=COC2=CC(O)=C(O)C=C2C1=O |
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InChI Identifier | InChI=1S/C15H10O5/c16-9-3-1-8(2-4-9)11-7-20-14-6-13(18)12(17)5-10(14)15(11)19/h1-7,16-18H |
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InChI Key | GYLUFQJZYAJQDI-UHFFFAOYSA-N |
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Experimental Spectra |
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| Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
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1D NMR | 13C NMR Spectrum (1D, 50 MHz, Dimethylsulfoxide-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 150 MHz, Dimethylsulfoxide-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 250 MHz, Dimethylsulfoxide-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 175 MHz, Dimethylsulfoxide-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 75 MHz, Dimethylsulfoxide-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 100 MHz, Dimethylsulfoxide-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 225 MHz, Dimethylsulfoxide-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 200 MHz, Dimethylsulfoxide-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 125 MHz, Dimethylsulfoxide-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 25 MHz, Dimethylsulfoxide-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, Dimethylsulfoxide-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, Dimethylsulfoxide-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, Dimethylsulfoxide-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, Dimethylsulfoxide-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, Dimethylsulfoxide-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, Dimethylsulfoxide-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, Dimethylsulfoxide-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, Dimethylsulfoxide-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, Dimethylsulfoxide-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, Dimethylsulfoxide-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| Predicted Spectra |
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| Not Available | 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 isoflavones. These are polycyclic compounds containing a 2-isoflavene skeleton which bears a ketone group at the C4 carbon atom. |
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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 | Isoflav-2-enes |
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Direct Parent | Isoflavones |
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Alternative Parents | |
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Substituents | - Isoflavone
- Hydroxyisoflavonoid
- Chromone
- Benzopyran
- 1-benzopyran
- Pyranone
- Phenol
- 1-hydroxy-2-unsubstituted benzenoid
- Benzenoid
- Monocyclic benzene moiety
- Pyran
- Heteroaromatic compound
- Oxacycle
- Organoheterocyclic compound
- Organooxygen compound
- Organic oxygen compound
- Hydrocarbon derivative
- Organic oxide
- 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 | - Chen YC, Sugiyama Y, Abe N, Kuruto-Niwa R, Nozawa R, Hirota A: DPPH radical-scavenging compounds from dou-chi, a soybean fermented food. Biosci Biotechnol Biochem. 2005 May;69(5):999-1006. doi: 10.1271/bbb.69.999. [PubMed:15914921 ]
- Esaki H, Kawakishi S, Morimitsu Y, Osawa T: New potent antioxidative o-dihydroxyisoflavones in fermented Japanese soybean products. Biosci Biotechnol Biochem. 1999 Sep;63(9):1637-9. doi: 10.1271/bbb.63.1637. [PubMed:10540753 ]
- Chen YC, Inaba M, Abe N, Hirota A: Antimutagenic activity of 8-hydroxyisoflavones and 6-hydroxydaidzein from soybean miso. Biosci Biotechnol Biochem. 2003 Apr;67(4):903-6. doi: 10.1271/bbb.67.903. [PubMed:12784638 ]
- Hirota A, Inaba M, Chen YC, Abe N, Taki S, Yano M, Kawaii S: Isolation of 8-hydroxyglycitein and 6-hydroxydaidzein from soybean miso. Biosci Biotechnol Biochem. 2004 Jun;68(6):1372-4. doi: 10.1271/bbb.68.1372. [PubMed:15215607 ]
- Hedlund TE, van Bokhoven A, Johannes WU, Nordeen SK, Ogden LG: Prostatic fluid concentrations of isoflavonoids in soy consumers are sufficient to inhibit growth of benign and malignant prostatic epithelial cells in vitro. Prostate. 2006 Apr 1;66(5):557-66. doi: 10.1002/pros.20380. [PubMed:16372328 ]
- Te-Sheng Chang, Hsiou-Yu Ding, Sorgan Shou-Ku Tai, Ching-Yi Wu (2007). Mushroom tyrosinase inhibitory effects of isoflavones isolated from soygerm koji fermented with Aspergillus oryzae BCRC 32288. Food Chemistry, Volume 105, Issue 4, 2007, Pages 1430-1438. DOI: 10.1016/j.foodchem.2007.05.019. Food Chemistry.
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