Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:04:39 UTC |
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Update date | 2019-11-26 02:55:06 UTC |
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Primary ID | FDB000624 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | Fisetin |
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Description | 3,7,3',4'-tetrahydroxyflavone, also known as 5-desoxyquercetin or fisetinidin, is a member of the class of 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, 3,7,3',4'-tetrahydroxyflavone is considered to be a flavonoid lipid molecule. 3,7,3',4'-tetrahydroxyflavone is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). 3,7,3',4'-tetrahydroxyflavone is a bitter tasting compound found in soy bean, which makes 3,7,3',4'-tetrahydroxyflavone a potential biomarker for the consumption of this food product. |
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CAS Number | 528-48-3 |
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Structure | |
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Synonyms | Synonym | Source |
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2-(3,4-Dihydroxyphenyl)-3,7-dihydroxy-4H-1-benzopyran-4-one | ChEBI | 3,3',4',7-Tetrahydroxyflavone | ChEBI | 3,7,3',4'-TETRAHYDROXYFLAVONE | ChEBI | 5-Desoxyquercetin | ChEBI | 7,3',4'-Trihydroxyflavonol | ChEBI | 3,3',4',7-Tetrahydroxy-flavone | MeSH | 5-Desoxy-quercetin | MeSH | Fisetinidin | MeSH | 2-(3,4-Dihydroxyphenyl)-3,7-dihydroxy-4H-benzopyran-4-one | PhytoBank | 3,3’,4’,7-Tetrahydroxyflavone | PhytoBank | Fiestin | PhytoBank | Fietin | PhytoBank | Fisetholz | PhytoBank | Fisitin | PhytoBank | Superfustel | PhytoBank | Superfustel K | PhytoBank | 2-(3,4-Dihydroxyphenyl)-3,7-dihydroxy-4H-1-benzopyran-4-one, 9CI | db_source | 3',4',7-Trihydroxyflavonol | db_source | Fisetin | db_source |
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Predicted Properties | |
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Chemical Formula | C15H10O6 |
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IUPAC name | 2-(3,4-dihydroxyphenyl)-3,7-dihydroxy-4H-chromen-4-one |
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InChI Identifier | InChI=1S/C15H10O6/c16-8-2-3-9-12(6-8)21-15(14(20)13(9)19)7-1-4-10(17)11(18)5-7/h1-6,16-18,20H |
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InChI Key | XHEFDIBZLJXQHF-UHFFFAOYSA-N |
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Isomeric SMILES | OC1=CC2=C(C=C1)C(=O)C(O)=C(O2)C1=CC(O)=C(O)C=C1 |
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Average Molecular Weight | 286.2363 |
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Monoisotopic Molecular Weight | 286.047738052 |
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Classification |
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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
- 7-hydroxyflavonoid
- Hydroxyflavonoid
- Chromone
- Benzopyran
- 1-benzopyran
- Catechol
- 1-hydroxy-4-unsubstituted benzenoid
- 1-hydroxy-2-unsubstituted benzenoid
- Phenol
- Pyranone
- Benzenoid
- Monocyclic benzene moiety
- Pyran
- Heteroaromatic compound
- Organoheterocyclic compound
- Oxacycle
- Hydrocarbon derivative
- Organooxygen compound
- Organic oxygen compound
- Organic oxide
- Aromatic heteropolycyclic compound
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Molecular Framework | Aromatic heteropolycyclic compounds |
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External Descriptors | |
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Ontology |
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Ontology | No ontology term |
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Physico-Chemical Properties |
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Physico-Chemical Properties - Experimental | Property | Value | Reference |
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Physical state | Not Available | |
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Physical Description | Not Available | |
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Mass Composition | C 62.94%; H 3.52%; O 33.54% | DFC |
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Melting Point | Not Available | |
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Boiling Point | Not Available | |
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Experimental Water Solubility | Not Available | |
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Experimental logP | Not Available | |
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Experimental pKa | Not Available | |
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Isoelectric point | Not Available | |
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Charge | Not Available | |
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Optical Rotation | Not Available | |
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Spectroscopic UV Data | 360 () (EtOH) (Berdy) | DFC |
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Density | Not Available | |
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Refractive Index | Not Available | |
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Spectra |
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Spectra | |
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EI-MS/GC-MS | Type | Description | Splash Key | View |
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Predicted GC-MS | Fisetin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0ab9-1690000000-d5039a5fb028f0a7256e | Spectrum |
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MS/MS | Type | Description | Splash Key | View |
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MS/MS | LC-MS/MS Spectrum - ESI-TOF 20V, Negative | splash10-0a4r-0290000000-5c8ad469168402341b9f | 2017-08-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF 10V, Negative | splash10-001i-0090000000-f3c523b1f1bc8f01642b | 2017-08-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF 40V, Negative | splash10-001i-0090000000-f3c523b1f1bc8f01642b | 2017-08-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF 20V, Negative | splash10-0a4r-0290000000-5c8ad469168402341b9f | 2017-09-12 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF 10V, Negative | splash10-001i-0090000000-f3c523b1f1bc8f01642b | 2017-09-12 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF 40V, Negative | splash10-00b9-0890000000-a1442e3e62aebd868ecc | 2017-09-12 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-000i-0090000000-c1553f0c611f67bf4f9d | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-000i-0590000000-d5ae2c650c208f2280a1 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-0f79-0940000000-01a46744a5b3400edf4e | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-0079-0920000000-e90e3306aeee5a3a860c | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-00du-2910000000-290829e57b6f173be8a6 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-000i-0390000000-5b81a7908f16f0a7ea48 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-000i-0090000000-d6424bbb654f1f6f9a3d | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , negative | splash10-03dr-0930000000-e2686cac73cb1e9d586c | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , negative | splash10-03dr-0930000000-fc2111437a5a1f4d2f76 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-TOF , negative | splash10-0a4r-0290000000-5c8ad469168402341b9f | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-TOF , negative | splash10-00b9-0890000000-a1442e3e62aebd868ecc | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-000i-0090000000-60a3ecd3089a9c06f89b | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-000i-0090000000-1ecacca5cc3e871c68dc | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-000i-0190000000-9735c20afc466c288b66 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-000i-0960000000-ca43a054785d31625955 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-000i-0920000000-76dea0f1763f3705a124 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-000i-0090000000-fa8ea3d7ca32952650d3 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-0a4s-0900000000-752f52a6aa237a03bea0 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , positive | splash10-01py-0390000000-5cddff1a8299cea287f7 | 2017-09-14 | View Spectrum |
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NMR | Not Available |
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External Links |
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ChemSpider ID | Not Available |
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ChEMBL ID | Not Available |
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KEGG Compound ID | C10041 |
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Pubchem Compound ID | 5281614 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | 42567 |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | DB07795 |
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HMDB ID | Not Available |
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CRC / DFC (Dictionary of Food Compounds) ID | BFF47-J:BFF47-J |
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EAFUS ID | Not Available |
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Dr. Duke ID | FISETIN |
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BIGG ID | Not Available |
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KNApSAcK ID | C00004579 |
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HET ID | Not Available |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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Flavornet ID | Not Available |
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GoodScent ID | Not Available |
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SuperScent ID | Not Available |
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Wikipedia ID | Fisetin |
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Phenol-Explorer Metabolite ID | Not Available |
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Duplicate IDS | Not Available |
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Old DFC IDS | Not Available |
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Associated Foods |
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Food | Content Range | Average | Reference |
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Food | | | Reference |
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Biological Effects and Interactions |
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Health Effects / Bioactivities | Descriptor | ID | Definition | Reference |
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5-lipoxygenase inhibitor | 23924 | A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. | DUKE | angiotensin converting enzyme inhibitor | 35457 | An EC 3.4.15.* (peptidyl-dipeptidase) inhibitor that interferes with the action of peptidyl-dipeptidase A (EC 3.4.15.1). | DUKE | allergenic | 50904 | A chemical compound which causes the onset of an allergic reaction by interacting with any of the molecular pathways involved in an allergy. | DUKE | anti histaminic | 37956 | Histamine antagonists are the drugs that bind to but do not activate histamine receptors, thereby blocking the actions of histamine or histamine agonists. | DUKE | anti mutagenic | | | DUKE | antioxidant | 22586 | A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324. | DUKE | anti viral | 22587 | A substance that destroys or inhibits replication of viruses. | DUKE | cyclooxygenase inhibitor | 35544 | A compound or agent that combines with cyclooxygenases (EC 1.14.99.1) and thereby prevents its substrate-enzyme combination with arachidonic acid and the formation of icosanoids, prostaglandins, and thromboxanes. | DUKE | iodothyronine-deiodinase inhibitor | 23924 | A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. | DUKE | lipoxygenase inhibitor | 35856 | A compound or agent that combines with lipoxygenase and thereby prevents its substrate-enzyme combination with arachidonic acid and the formation of the icosanoid products hydroxyicosatetraenoic acid and various leukotrienes. | DUKE | oxidase inhibitor | 23924 | A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. | DUKE | pesticide | 25944 | Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests. | DUKE | topoisomerase-II inhibitor | 50750 | A topoisomerase inhibitor that inhibits DNA topoisomerase (ATP-hydrolysing), EC 5.99.1.3 (topoisomerase II), which catalyses ATP-dependent breakage of both strands of DNA, passage of the unbroken strands through the breaks, and rejoining of the broken strands. | DUKE | topoisomerase-I inhibitor | 50276 | A topoisomerase inhibitor that inhibits the bacterial enzymes of the DNA topoisomerases, Type I class (EC 5.99.1.2) that catalyze ATP-independent breakage of one of the two strands of DNA, passage of the unbroken strand through the break, and rejoining of the broken strand. These bacterial enzymes reduce the topological stress in the DNA structure by relaxing negatively, but not positively, supercoiled DNA. | DUKE |
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Enzymes | Not Available |
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Pathways | Not Available |
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Metabolism | Not Available |
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Biosynthesis | Not Available |
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Organoleptic Properties |
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Flavours | Flavor | Citations |
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bitter |
- Ayana Wiener, Marina Shudler, Anat Levit, Masha Y. Niv. BitterDB: a database of bitter compounds. Nucleic Acids Res 2012, 40(Database issue):D413-419. DOI:10.1093/nar/gkr755
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Files |
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MSDS | Not Available |
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References |
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Synthesis Reference | Not Available |
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General Reference | Not Available |
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Content Reference | — Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
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