Record Information |
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Version | 1.0 |
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Created at | 2021-06-22 17:42:57 UTC |
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Updated at | 2021-08-20 00:00:49 UTC |
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NP-MRD ID | NP0043961 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | Robinetin |
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Description | Robinetin, also known as 5-deoxymyricetin or 5-hydroxyfisetin, belongs to the class of organic compounds known as flavonols. Flavonols are compounds that contain a flavone (2-phenyl-1-benzopyran-4-one) backbone carrying a hydroxyl group at the 3-position. Thus, robinetin is considered to be a flavonoid. Robinetin is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Robinetin is found in Burkea africana. It was first documented in 2005 (PMID: 16132219). Based on a literature review a significant number of articles have been published on robinetin (PMID: 27719955) (PMID: 19914085) (PMID: 25313717) (PMID: 25482106). |
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Structure | OC1=CC2=C(C=C1)C(=O)C(O)=C(O2)C1=CC(O)=C(O)C(O)=C1 InChI=1S/C15H10O7/c16-7-1-2-8-11(5-7)22-15(14(21)12(8)19)6-3-9(17)13(20)10(18)4-6/h1-5,16-18,20-21H |
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Synonyms | Value | Source |
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5-Deoxymyricetin | ChEBI | 5-Hydroxyfisetin | ChEBI | 3,7-Dihydroxy-2-(3,4,5-trihydroxyphenyl)-4H-1-benzopyran-4-one | MeSH |
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Chemical Formula | C15H10O7 |
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Average Mass | 302.2380 Da |
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Monoisotopic Mass | 302.04265 Da |
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IUPAC Name | 3,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-4H-chromen-4-one |
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Traditional Name | robinetin |
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CAS Registry Number | Not Available |
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SMILES | OC1=CC2=C(C=C1)C(=O)C(O)=C(O2)C1=CC(O)=C(O)C(O)=C1 |
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InChI Identifier | InChI=1S/C15H10O7/c16-7-1-2-8-11(5-7)22-15(14(21)12(8)19)6-3-9(17)13(20)10(18)4-6/h1-5,16-18,20-21H |
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InChI Key | SOEDEYVDCDYMMH-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, 150 MHz, Pyridine-d5, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, Pyridine-d5, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 50 MHz, Pyridine-d5, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 250 MHz, Pyridine-d5, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 175 MHz, Pyridine-d5, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 75 MHz, Pyridine-d5, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 100 MHz, Pyridine-d5, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 225 MHz, Pyridine-d5, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 200 MHz, Pyridine-d5, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 125 MHz, Pyridine-d5, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 25 MHz, Pyridine-d5, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, Pyridine-d5, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, Pyridine-d5, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, Pyridine-d5, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, Pyridine-d5, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, Pyridine-d5, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, Pyridine-d5, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, Pyridine-d5, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, Pyridine-d5, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, Pyridine-d5, 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 flavonols. Flavonols are compounds that contain a flavone (2-phenyl-1-benzopyran-4-one) backbone carrying a hydroxyl group at the 3-position. |
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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 | Flavones |
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Direct Parent | Flavonols |
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Alternative Parents | |
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Substituents | - 3-hydroxyflavone
- 3'-hydroxyflavonoid
- 3-hydroxyflavonoid
- 4'-hydroxyflavonoid
- Hydroxyflavonoid
- 7-hydroxyflavonoid
- Chromone
- Benzopyran
- 1-benzopyran
- Benzenetriol
- Pyrogallol derivative
- 1-hydroxy-4-unsubstituted benzenoid
- 1-hydroxy-2-unsubstituted benzenoid
- Phenol
- Pyranone
- Benzenoid
- Monocyclic benzene moiety
- Pyran
- Heteroaromatic compound
- Oxacycle
- Organoheterocyclic compound
- Polyol
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen 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 | |
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Predicted Properties | |
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General References | - Blunder M, Orthaber A, Bauer R, Bucar F, Kunert O: Efficient identification of flavones, flavanones and their glycosides in routine analysis via off-line combination of sensitive NMR and HPLC experiments. Food Chem. 2017 Mar 1;218:600-609. doi: 10.1016/j.foodchem.2016.09.077. Epub 2016 Sep 13. [PubMed:27719955 ]
- Nasir H, Iqbal Z, Hiradate S, Fujii Y: Allelopathic potential of Robinia pseudo-acacia L. J Chem Ecol. 2005 Sep;31(9):2179-92. doi: 10.1007/s10886-005-6084-5. Epub 2005 Aug 17. [PubMed:16132219 ]
- Chaudhuri S, Pahari B, Sengupta B, Sengupta PK: Binding of the bioflavonoid robinetin with model membranes and hemoglobin: Inhibition of lipid peroxidation and protein glycosylation. J Photochem Photobiol B. 2010 Jan 21;98(1):12-9. doi: 10.1016/j.jphotobiol.2009.10.002. Epub 2009 Nov 13. [PubMed:19914085 ]
- Pahari BP, Chaudhuri S, Chakraborty S, Sengupta PK: Ground and excited state proton transfer of the bioactive plant flavonol robinetin in a protein environment: spectroscopic and molecular modeling studies. J Phys Chem B. 2015 Feb 12;119(6):2533-45. doi: 10.1021/jp508410v. Epub 2014 Oct 27. [PubMed:25313717 ]
- Germano MP, Certo G, D'Angelo V, Sanogo R, Malafronte N, De Tommasi N, Rapisarda A: Anti-angiogenic activity of Entada africana root. Nat Prod Res. 2015;29(16):1551-6. doi: 10.1080/14786419.2014.987773. Epub 2014 Dec 6. [PubMed:25482106 ]
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