Record Information
Version1.0
Creation date2010-04-08 22:04:39 UTC
Update date2019-11-26 02:55:06 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
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 - Experimental
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-0290000000-5c8ad469168402341b9fSpectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-001i-0090000000-f3c523b1f1bc8f01642bSpectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-001i-0090000000-f3c523b1f1bc8f01642bSpectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-0a4r-0290000000-5c8ad469168402341b9fSpectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-001i-0090000000-f3c523b1f1bc8f01642bSpectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-00b9-0890000000-a1442e3e62aebd868eccSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-000i-0090000000-c1553f0c611f67bf4f9dSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-000i-0590000000-d5ae2c650c208f2280a1Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0f79-0940000000-01a46744a5b3400edf4eSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0079-0920000000-e90e3306aeee5a3a860cSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-00du-2910000000-290829e57b6f173be8a6Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-000i-0390000000-5b81a7908f16f0a7ea48Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-000i-0090000000-d6424bbb654f1f6f9a3dSpectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-03dr-0930000000-e2686cac73cb1e9d586cSpectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-03dr-0930000000-fc2111437a5a1f4d2f76Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-0a4r-0290000000-5c8ad469168402341b9fSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-00b9-0890000000-a1442e3e62aebd868eccSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-000i-0090000000-60a3ecd3089a9c06f89bSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-000i-0090000000-1ecacca5cc3e871c68dcSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0090000000-6d3e3fae302b13749b3cSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0190000000-fa6ae23672d8fb2c4efbSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05tr-9850000000-14051005517b6d072cd0Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-102aac56e2bc55e0dcfcSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0190000000-69c5e8b68799012b7919Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014l-4940000000-9709db31d8ea67c1140bSpectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
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 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 inhibitor35457 An EC 3.4.15.* (peptidyl-dipeptidase) inhibitor that interferes with the action of peptidyl-dipeptidase A (EC 3.4.15.1).DUKE
allergenic50904 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 histaminic37956 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 mutagenicDUKE
antioxidant22586 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 viral22587 A substance that destroys or inhibits replication of viruses.DUKE
cyclooxygenase inhibitor35544 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 inhibitor23924 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 inhibitor35856 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 inhibitor23924 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
pesticide25944 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 inhibitor50750 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 inhibitor50276 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
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).