Record Information |
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Version | 2.0 |
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Created at | 2006-05-22 15:12:08 UTC |
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Updated at | 2024-09-03 04:19:09 UTC |
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NP-MRD ID | NP0000618 |
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Natural Product DOI | https://doi.org/10.57994/1652 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | Myricetin |
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Description | Myricetin, also known as cannabiscetin or myricetol, 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, myricetin is considered to be a flavonoid lipid molecule. A hexahydroxyflavone that is flavone substituted by hydroxy groups at positions 3, 3', 4', 5, 5' and 7. Myricetin is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Myricetin is found, on average, in the highest concentration within a few different foods, such as common walnuts, carobs, and fennels and in a lower concentration in welsh onions, yellow bell peppers, and jutes. Myricetin has also been detected, but not quantified in several different foods, such as napa cabbages, sesames, mixed nuts, lichee, and garden cress. |
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Structure | OC1=CC(O)=C2C(OC(=C(O)C2=O)C2=CC(O)=C(O)C(O)=C2)=C1 InChI=1S/C15H10O8/c16-6-3-7(17)11-10(4-6)23-15(14(22)13(11)21)5-1-8(18)12(20)9(19)2-5/h1-4,16-20,22H |
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Synonyms | Value | Source |
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3,3',4',5,5',7-Hexahydroxyflavone | ChEBI | 3,5,7,3',4',5'-Hexahydroxyflavone | ChEBI | Cannabiscetin | ChEBI | Myricetol | ChEBI | 3,3',4',5,5',7-Hexahydroxy-(8ci)- flavone | HMDB | 3,5,7-Trihydroxy-2-(3,4,5-trihydroxyphenyl)-4H-1-benzopyran-4-one | HMDB | 3,3’,4’,5,5’,7-hexahydroxyflavone | HMDB | 3,5,7,3’,4’,5’-hexahydroxyflavone | HMDB |
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Chemical Formula | C15H10O8 |
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Average Mass | 318.2351 Da |
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Monoisotopic Mass | 318.03757 Da |
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IUPAC Name | 3,5,7-trihydroxy-2-(3,4,5-trihydroxyphenyl)-4H-chromen-4-one |
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Traditional Name | myricetin |
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CAS Registry Number | 529-44-2 |
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SMILES | OC1=CC(O)=C2C(OC(=C(O)C2=O)C2=CC(O)=C(O)C(O)=C2)=C1 |
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InChI Identifier | InChI=1S/C15H10O8/c16-6-3-7(17)11-10(4-6)23-15(14(22)13(11)21)5-1-8(18)12(20)9(19)2-5/h1-4,16-20,22H |
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InChI Key | IKMDFBPHZNJCSN-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 | 1H NMR Spectrum (1D, 600 MHz, Methanol, simulated) | Varshavi.d26 | | | 2021-09-06 | View Spectrum | HSQC NMR | [1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental) | bgnzk@missouri.edu | Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA | Dr. Bharat Goel | 2024-06-18 | View Spectrum | HMBC NMR | [1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental) | bgnzk@missouri.edu | Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA | Dr. Bharat Goel | 2024-06-18 | View Spectrum | COSY NMR | [1H, 1H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental) | bgnzk@missouri.edu | Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA | Dr. Bharat Goel | 2024-06-18 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 201 MHz, CD3OD, experimental) | bgnzk@missouri.edu | Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA | Dr. Bharat Goel | 2024-06-18 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental) | bgnzk@missouri.edu | Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA | Dr. Bharat Goel | 2024-06-18 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 201 MHz, CD3OD, experimental) | ztmnb@umsystem.edu | Sumner lab, University of Missouri | Zach Tretter | 2024-01-23 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, CD3OD, experimental) | ztmnb@umsystem.edu | Sumner lab, University of Missouri | Zach Tretter | 2024-01-23 | View Spectrum | 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 | 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental) | 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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| Chemical Shift Submissions |
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| Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
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1D NMR | 1H NMR Spectrum (1D, 600, CD3OD, simulated) | bgnzk@missouri.edu | Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA | Dr. Bharat Goel | 2024-06-18 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, Methanol, simulated) | varshavi.d26@gmail.com | Not Available | Not Available | 2021-08-16 | View Spectrum |
| 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
- 5-hydroxyflavonoid
- 7-hydroxyflavonoid
- 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
- Vinylogous acid
- Oxacycle
- Organoheterocyclic compound
- Polyol
- Organic oxide
- Organic oxygen compound
- 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 | Solid |
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Experimental Properties | |
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Predicted Properties | |
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General References | - Noroozi M, Burns J, Crozier A, Kelly IE, Lean ME: Prediction of dietary flavonol consumption from fasting plasma concentration or urinary excretion. Eur J Clin Nutr. 2000 Feb;54(2):143-9. [PubMed:10694785 ]
- Noguchi Y, Fukuda K, Matsushima A, Haishi D, Hiroto M, Kodera Y, Nishimura H, Inada Y: Inhibition of Df-protease associated with allergic diseases by polyphenol. J Agric Food Chem. 1999 Aug;47(8):2969-72. [PubMed:10552595 ]
- Tong Y, Zhou XM, Wang SJ, Yang Y, Cao YL: Analgesic activity of myricetin isolated from Myrica rubra Sieb. et Zucc. leaves. Arch Pharm Res. 2009 Apr;32(4):527-33. doi: 10.1007/s12272-009-1408-6. Epub 2009 Apr 29. [PubMed:19407970 ]
- Huang JH, Huang CC, Fang JY, Yang C, Chan CM, Wu NL, Kang SW, Hung CF: Protective effects of myricetin against ultraviolet-B-induced damage in human keratinocytes. Toxicol In Vitro. 2010 Feb;24(1):21-8. doi: 10.1016/j.tiv.2009.09.015. Epub 2009 Sep 22. [PubMed:19778600 ]
- Sun F, Zheng XY, Ye J, Wu TT, Wang Jl, Chen W: Potential anticancer activity of myricetin in human T24 bladder cancer cells both in vitro and in vivo. Nutr Cancer. 2012;64(4):599-606. doi: 10.1080/01635581.2012.665564. Epub 2012 Apr 6. [PubMed:22482362 ]
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