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Showing Compound Fisetin (FDB000624)

Record Information
Version1.0
Creation date2010-04-08 22:04:39 UTC
Update date2025-11-18 22:20:29 UTC
Primary IDFDB000624
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameFisetin
Description3,7,3',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.
CAS Number528-48-3
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
2-(3,4-Dihydroxyphenyl)-3,7-dihydroxy-4H-1-benzopyran-4-oneChEBI
3,3',4',7-TetrahydroxyflavoneChEBI
3,7,3',4'-TETRAHYDROXYFLAVONEChEBI
5-DesoxyquercetinChEBI
7,3',4'-TrihydroxyflavonolChEBI
3,3',4',7-Tetrahydroxy-flavoneMeSH
5-Desoxy-quercetinMeSH
FisetinidinMeSH
2-(3,4-Dihydroxyphenyl)-3,7-dihydroxy-4H-benzopyran-4-onePhytoBank
3,3’,4’,7-TetrahydroxyflavonePhytoBank
FiestinPhytoBank
FietinPhytoBank
FisetholzPhytoBank
FisitinPhytoBank
SuperfustelPhytoBank
Superfustel KPhytoBank
2-(3,4-Dihydroxyphenyl)-3,7-dihydroxy-4H-1-benzopyran-4-one, 9CIdb_source
3',4',7-Trihydroxyflavonoldb_source
Fisetindb_source
Predicted Properties
PropertyValueSource
Water Solubility0.15 g/LALOGPS
logP2.03ALOGPS
logP1.81ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)6.32ChemAxon
pKa (Strongest Basic)-3.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area107.22 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity74.88 m³·mol⁻¹ChemAxon
Polarizability27.64 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC15H10O6
IUPAC name2-(3,4-dihydroxyphenyl)-3,7-dihydroxy-4H-chromen-4-one
InChI IdentifierInChI=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
InChI KeyXHEFDIBZLJXQHF-UHFFFAOYSA-N
Isomeric SMILESOC1=CC2=C(C=C1)C(=O)C(O)=C(O2)C1=CC(O)=C(O)C=C1
Average Molecular Weight286.2363
Monoisotopic Molecular Weight286.047738052
Classification
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.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavones
Direct ParentFlavonols
Alternative Parents
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
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 62.94%; H 3.52%; O 33.54%DFC
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV Data360 () (EtOH) (Berdy)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSFisetin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0ab9-1690000000-d5039a5fb028f0a7256eSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-0a4r-0290000000-5c8ad469168402341b9f2017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-001i-0090000000-f3c523b1f1bc8f01642b2017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-001i-0090000000-f3c523b1f1bc8f01642b2017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-0a4r-0290000000-5c8ad469168402341b9f2017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-001i-0090000000-f3c523b1f1bc8f01642b2017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-00b9-0890000000-a1442e3e62aebd868ecc2017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-000i-0090000000-c1553f0c611f67bf4f9d2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-000i-0590000000-d5ae2c650c208f2280a12017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0f79-0940000000-01a46744a5b3400edf4e2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0079-0920000000-e90e3306aeee5a3a860c2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-00du-2910000000-290829e57b6f173be8a62017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-000i-0390000000-5b81a7908f16f0a7ea482017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-000i-0090000000-d6424bbb654f1f6f9a3d2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-03dr-0930000000-e2686cac73cb1e9d586c2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-03dr-0930000000-fc2111437a5a1f4d2f762017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-0a4r-0290000000-5c8ad469168402341b9f2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-00b9-0890000000-a1442e3e62aebd868ecc2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-000i-0090000000-60a3ecd3089a9c06f89b2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-000i-0090000000-1ecacca5cc3e871c68dc2017-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0090000000-6d3e3fae302b13749b3c2016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0190000000-fa6ae23672d8fb2c4efb2016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05tr-9850000000-14051005517b6d072cd02016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-102aac56e2bc55e0dcfc2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0190000000-69c5e8b68799012b79192016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014l-4940000000-9709db31d8ea67c1140b2016-08-03View Spectrum
NMRNot Available
ChemSpider ID4444933
ChEMBL IDCHEMBL31574
KEGG Compound IDC10041
Pubchem Compound ID5281614
Pubchem Substance IDNot Available
ChEBI ID42567
Phenol-Explorer IDNot Available
DrugBank IDDB07795
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDBFF47-J:BFF47-J
EAFUS IDNot Available
Dr. Duke IDFISETIN
BIGG IDNot Available
KNApSAcK IDC00004579
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDFisetin
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
5-lipoxygenase inhibitor23924 An agent that blocks the activity of 5-lipoxygenase, an enzyme involved in leukotriene production, reducing inflammation and allergic responses. Therapeutically, it's used to treat asthma, allergies, and inflammatory disorders, such as arthritis, by inhibiting the synthesis of pro-inflammatory leukotrienes.DUKE
Angiotensin converting enzyme inhibitor35457 An agent that blocks the conversion of angiotensin I to angiotensin II, reducing blood pressure and fluid retention. Therapeutically, it's used to treat hypertension, heart failure, and protect kidney function in diabetes, thereby reducing the risk of cardiovascular disease and stroke.DUKE
Allergenic50904 A substance that triggers an immune response, causing allergic reactions. Its biological role is to stimulate the immune system, but it has no therapeutic applications. Key medical uses include diagnosing allergies and developing immunotherapies to desensitize patients to specific allergens, reducing the risk of severe reactions.DUKE
Anti histaminic37956 An agent that blocks histamine receptors, reducing allergic symptoms. Therapeutically, it alleviates itching, sneezing, and runny nose, commonly used in managing allergies, itching, and hives, as well as treating conditions like anaphylaxis and allergic rhinitis.DUKE
Anti-mutagenicAn agent that interferes with the mutagenicity of a substance, preventing DNA damage and mutations. Its biological role is to protect cells from genetic alterations, and it has therapeutic applications in cancer prevention and treatment, as well as key medical uses in reducing the risk of genetic disorders and birth defects.DUKE
Anti-oxidant22586 An agent that neutralizes free radicals, reducing oxidative stress and cell damage. Its biological role involves protecting cells from harm, and it has therapeutic applications in managing chronic diseases, such as cancer, diabetes, and neurodegenerative disorders, with key medical uses including anti-aging, anti-inflammatory, and cardio protective effects.DUKE
Anti-viral22587 An agent that inhibits the replication of viruses, playing a crucial role in preventing and treating viral infections. Therapeutically, anti-virals are used to manage diseases such as HIV, herpes, and influenza, reducing symptoms and slowing disease progression. Key medical uses include treating viral hepatitis, respiratory syncytial virus, and COVID-19.DUKE
Cyclooxygenase inhibitor35544 An agent that blocks the activity of cyclooxygenase enzymes, reducing inflammation and pain. Therapeutically, it is used to treat conditions such as arthritis, headaches, and menstrual cramps, by decreasing prostaglandin production, a key mediator of inflammation.DUKE
Iodothyronine-deiodinase inhibitor23924 An agent that blocks the activity of iodothyronine-deiodinase, regulating thyroid hormone levels. It is used therapeutically to manage thyroid disorders, particularly in cases of hyperthyroidism, and has potential applications in treating thyroid-related conditions, such as Graves' disease and thyroid cancer.DUKE
Lipoxygenase inhibitor35856 An agent that blocks the activity of lipoxygenase enzymes, reducing inflammation and oxidative stress. Therapeutically, it's used to manage conditions like asthma, atherosclerosis, and cancer, by inhibiting the production of pro-inflammatory leukotrienes. Key medical uses include treating respiratory and cardiovascular diseases.DUKE
Oxidase inhibitor23924 An agent that blocks the activity of oxidase enzymes, reducing oxidative stress. Therapeutically, it's used to treat conditions like Parkinson's disease, and has applications in managing neurodegenerative disorders, cardiovascular disease, and cancer, by mitigating oxidative damage and inflammation.DUKE
Pesticide25944 An agent that kills or repels pests, playing a biological role in controlling insect, weed, and fungal populations. Therapeutically, pesticides have limited applications, but some are used to treat ectoparasitic infestations, such as lice and scabies. Key medical uses include topical treatments for head lice and scabies, highlighting their role in managing parasitic infections.DUKE
Topoisomerase-II inhibitor50750 An agent that blocks the activity of topoisomerase-II, an enzyme involved in DNA replication. It prevents cancer cell growth by disrupting DNA structure, commonly used in chemotherapy to treat various types of cancer, including leukemia and lymphoma.DUKE
Topoisomerase-I inhibitor50276 An agent that blocks the activity of topoisomerase I, an enzyme involved in DNA replication. It is used therapeutically in cancer treatment, particularly for solid tumors, by inducing DNA damage and inhibiting cancer cell growth, with key medical uses in colorectal, lung, and breast cancers.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
bitter
  1. 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
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).