Record Information |
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Version | 1.0 |
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Created at | 2021-06-22 17:44:20 UTC |
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Updated at | 2021-06-22 17:44:20 UTC |
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NP-MRD ID | NP0043991 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | Tectoridin |
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Description | Tectoridin, also known as shekanin, 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. Tectoridin is found in Balameanda chinensis, Belamcanda chinensis , Iris leptophylla, Iris milesii, Maackia amurensis, Polygonatum odoratum, Psammosilene tunicoides, Pueraria montana, Pueraria thunbergiana and Sophora japonica . It was first documented in 2014 (PMID: 24252334). Based on a literature review a significant number of articles have been published on tectoridin (PMID: 25920391) (PMID: 34196922) (PMID: 33779496) (PMID: 33683556). |
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Structure | COC1=C(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)C=C2OC=C(C(=O)C2=C1O)C1=CC=C(O)C=C1 InChI=1S/C22H22O11/c1-30-21-13(32-22-20(29)19(28)17(26)14(7-23)33-22)6-12-15(18(21)27)16(25)11(8-31-12)9-2-4-10(24)5-3-9/h2-6,8,14,17,19-20,22-24,26-29H,7H2,1H3/t14-,17-,19+,20-,22-/m1/s1 |
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Synonyms | Value | Source |
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Shekanin | ChEBI | Tectorigenin 7-glucoside | MeSH |
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Chemical Formula | C22H22O11 |
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Average Mass | 462.4035 Da |
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Monoisotopic Mass | 462.11621 Da |
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IUPAC Name | 5-hydroxy-3-(4-hydroxyphenyl)-6-methoxy-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-chromen-4-one |
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Traditional Name | tectoridin |
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CAS Registry Number | Not Available |
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SMILES | COC1=C(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)C=C2OC=C(C(=O)C2=C1O)C1=CC=C(O)C=C1 |
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InChI Identifier | InChI=1S/C22H22O11/c1-30-21-13(32-22-20(29)19(28)17(26)14(7-23)33-22)6-12-15(18(21)27)16(25)11(8-31-12)9-2-4-10(24)5-3-9/h2-6,8,14,17,19-20,22-24,26-29H,7H2,1H3/t14-,17-,19+,20-,22-/m1/s1 |
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InChI Key | CNOURESJATUGPN-UDEBZQQRSA-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, 75 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 | 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, 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, 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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| Spectrum Type | Description | Depositor ID | Depositor Organization | Depositor | Deposition Date | View |
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1D NMR | 13C NMR Spectrum (1D, 50 MHz, dmso, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 150 MHz, dmso, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 250 MHz, dmso, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 175 MHz, dmso, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 75 MHz, dmso, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 100 MHz, dmso, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 225 MHz, dmso, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 200 MHz, dmso, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 125 MHz, dmso, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 25 MHz, dmso, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, dmso, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, dmso, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, dmso, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, dmso, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, dmso, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, dmso, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, dmso, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, dmso, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, dmso, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, dmso, 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 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 o-glycoside
- Isoflavonoid-7-o-glycoside
- Hydroxyisoflavonoid
- Isoflavone
- Phenolic glycoside
- Hexose monosaccharide
- Chromone
- Glycosyl compound
- O-glycosyl compound
- Benzopyran
- 1-benzopyran
- Anisole
- Alkyl aryl ether
- 1-hydroxy-4-unsubstituted benzenoid
- 1-hydroxy-2-unsubstituted benzenoid
- Phenol
- Pyranone
- Benzenoid
- Pyran
- Oxane
- Monocyclic benzene moiety
- Monosaccharide
- Heteroaromatic compound
- Vinylogous acid
- Secondary alcohol
- Oxacycle
- Polyol
- Ether
- Acetal
- Organoheterocyclic compound
- Hydrocarbon derivative
- Organic oxide
- Organic oxygen compound
- Organooxygen compound
- Primary alcohol
- Alcohol
- 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 | - Shim M, Bae JY, Lee YJ, Ahn MJ: Tectoridin from Maackia amurensis modulates both estrogen and thyroid receptors. Phytomedicine. 2014 Apr 15;21(5):602-6. doi: 10.1016/j.phymed.2013.10.022. Epub 2013 Nov 16. [PubMed:24252334 ]
- Li Y, Wang Q, He J, Yan J, Li H: Fluorescence spectroscopy and docking study in two flavonoids, isolated tectoridin and its aglycone tectorigenin, interacting with human serum albumin: a comparison study. Luminescence. 2016 Feb;31(1):38-46. doi: 10.1002/bio.2918. Epub 2015 Apr 28. [PubMed:25920391 ]
- Huang J, Li J, Yue J, Huang Z, Zhang L, Yao W, Guan R, Wu J, Liang J, Duan L, Ji A: Functional Characterization of a Novel Glycosyltransferase (UGT73CD1) from Iris tectorum Maxim. for the Substrate promiscuity. Mol Biotechnol. 2021 Jul 1. pii: 10.1007/s12033-021-00364-1. doi: 10.1007/s12033-021-00364-1. [PubMed:34196922 ]
- Liu J, Xia TR: Identification of the metabolites produced following Iris tectorum Maxim oral administration and a network pharmacology-based analysis of their potential pharmacological properties. Xenobiotica. 2021 Jun;51(6):680-688. doi: 10.1080/00498254.2021.1907473. Epub 2021 Apr 7. [PubMed:33779496 ]
- Xiong L, Guo W, Yang Y, Gao D, Wang J, Qu Y, Zhang Y: Tectoridin inhibits the progression of colon cancer through downregulating PKC/p38 MAPK pathway. Mol Cell Biochem. 2021 Jul;476(7):2729-2738. doi: 10.1007/s11010-021-04081-w. Epub 2021 Mar 8. [PubMed:33683556 ]
- Hee-Juhn Park, Jong-Hee Park, Jeon-Ok Moon, Kyung-Tae Lee, Won-Tae Jung, Sei-Ryang Oh, Hyeong-Kyu Lee (1999). Hee-Juhn Park, Jong-Hee Park, Jeon-Ok Moon, Kyung-Tae Lee, Won-Tae Jung, Sei-Ryang Oh, Hyeong-Kyu Lee. Isoflavone glycosides from the flowers of Puerariathunbergiana. Phytochemistry Volume 51, Issue 1, 10 May 1999, Pages 147-151 DOI: 10.1016/S0031-9422(98)00729-8. Phytochemistry.
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