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Showing Compound Quercetagetin (FDB011897)

Record Information
Version1.0
Creation date2010-04-08 22:09:53 UTC
Update date2020-02-24 19:11:05 UTC
Primary IDFDB011897
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameQuercetagetin
Description2-(3,4-dihydroxyphenyl)-3,5,6,7-tetrahydroxy-4h-chromen-4-one, also known as 6-hydroxyquercetin or 3,3',4',5,6,7-hexahydroxyflavone, 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, 2-(3,4-dihydroxyphenyl)-3,5,6,7-tetrahydroxy-4h-chromen-4-one is considered to be a flavonoid lipid molecule. 2-(3,4-dihydroxyphenyl)-3,5,6,7-tetrahydroxy-4h-chromen-4-one is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). 2-(3,4-dihydroxyphenyl)-3,5,6,7-tetrahydroxy-4h-chromen-4-one can be synthesized from quercetin. 2-(3,4-dihydroxyphenyl)-3,5,6,7-tetrahydroxy-4h-chromen-4-one is also a parent compound for other transformation products, including but not limited to, axillarin, eupatin, and patuletin. 2-(3,4-dihydroxyphenyl)-3,5,6,7-tetrahydroxy-4h-chromen-4-one is a bitter tasting compound found in sweet orange, which makes 2-(3,4-dihydroxyphenyl)-3,5,6,7-tetrahydroxy-4h-chromen-4-one a potential biomarker for the consumption of this food product.
CAS Number90-18-6
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
2-(3,4-Dihydroxyphenyl)-3,5,6,7-tetrahydroxy-4-benzopyroneChEBI
3,3',4',5,6,7-HexahydroxyflavoneChEBI
6-HydroxyquercetinChEBI
3,5,6,7,3',4'-HexamethoxyflavoneMeSH
3,5,6,7-Tetrahydroxy-2-(3,4-dihydroxyphenyl)-4H-1-benzopyran-4-oneMeSH
QuercetogetinMeSH
2-(3,4-Dihydroxyphenyl)-3,5,6,7-tetrahydroxy-4H-1-benzopyran-4-one, 9CIdb_source
3',4',5,6,7-Pentahydroxyflavonoldb_source
Quercetagetindb_source
Predicted Properties
PropertyValueSource
Water Solubility0.32 g/LALOGPS
logP1.7ALOGPS
logP1.85ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)6.56ChemAxon
pKa (Strongest Basic)-4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area147.68 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity78.84 m³·mol⁻¹ChemAxon
Polarizability29.49 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC15H10O8
IUPAC name2-(3,4-dihydroxyphenyl)-3,5,6,7-tetrahydroxy-4H-chromen-4-one
InChI IdentifierInChI=1S/C15H10O8/c16-6-2-1-5(3-7(6)17)15-14(22)13(21)10-9(23-15)4-8(18)11(19)12(10)20/h1-4,16-20,22H
InChI KeyZVOLCUVKHLEPEV-UHFFFAOYSA-N
Isomeric SMILESOC1=CC2=C(C(O)=C1O)C(=O)C(O)=C(O2)C1=CC(O)=C(O)C=C1
Average Molecular Weight318.2351
Monoisotopic Molecular Weight318.037567296
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
  • 5-hydroxyflavonoid
  • 6-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Hydroxyflavonoid
  • Chromone
  • Benzopyran
  • 1-benzopyran
  • Catechol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Pyranone
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Pyran
  • Vinylogous acid
  • Heteroaromatic compound
  • Organoheterocyclic compound
  • Oxacycle
  • Polyol
  • Organic oxide
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Source:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 56.61%; H 3.17%; O 40.22%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 Data361 (e 21877) (MeOH) (Berdy)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSQuercetagetin, 5 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0900-1212109000-3d0cb1e71bc3f80f051eSpectrum
Predicted GC-MSQuercetagetin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0f79-0792000000-663986ef797f12ea62e8Spectrum
Predicted GC-MSQuercetagetin, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT 22V, positivesplash10-01b9-0397000000-9ad48bd249a3aa567ce02020-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-IT 22V, positivesplash10-0g4j-0492000000-c7770d50d16d1d0b80842020-07-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0009000000-e0804a88f8274e655f902016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0349000000-4d74a79028a275bf77d72016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0l6r-4920000000-691c34c0f5798b9cc7542016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0119000000-1642b5f1d7c819f7c7572016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0479000000-ed9d9b0a589026bce21b2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00xr-7940000000-0ef9c3a3a5bb3639b66c2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0009000000-4329fbc3ab22500675af2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0619000000-3882a151bd0697d162f22021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-06di-1920000000-e89690a0c34929e973b82021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0009000000-9dd1047022f2116af9632021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0009000000-c73aca74b75a03dfe2c42021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-1912000000-282b925a12b2ab6547aa2021-09-24View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID354
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDHBP96-H:HBP96-H
EAFUS IDNot Available
Dr. Duke IDQUERCETAGETIN
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
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
Aldose reductase inhibitor48550 An agent that blocks the activity of aldose reductase, an enzyme involved in glucose metabolism. It reduces oxidative stress and inflammation, commonly used in managing diabetic complications, such as neuropathy, nephropathy, and retinopathy.DUKE
Anti bacterial33282 An agent that inhibits the growth of or destroys bacteria, playing a crucial role in preventing and treating infections. Therapeutically, it is used to combat bacterial infections, with key medical applications including treating pneumonia, tuberculosis, and skin infections, as well as preventing surgical site infections and sepsis.DUKE
Anti HIV22587 An agent that prevents the replication of the Human Immunodeficiency Virus (HIV), used to treat and manage HIV infection and Acquired Immunodeficiency Syndrome (AIDS), reducing viral load and slowing disease progression.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
Dye37958 A coloring agent with various biological roles, therapeutic applications, and medical uses, including diagnostic imaging, photodynamic therapy, and wound healing, while also serving as a contrast agent to enhance visualization in medical imaging procedures.DUKE
HIV-reverse-transcriptase inhibitor23924 An agent that blocks the activity of reverse transcriptase, an enzyme essential for HIV replication, reducing viral load and slowing disease progression. Therapeutically, it is used to treat HIV/AIDS, often in combination with other antiretroviral medications to prevent drug resistance and manage symptoms.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
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).