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Showing Compound 2-(3,4-Dihydroxyphenyl)-5,6-dihydroxy-7-methoxy-4H-1-benzopyran-4-one (FDB002746)

Record Information
Version1.0
Creation date2010-04-08 22:05:30 UTC
Update date2020-02-24 19:10:37 UTC
Primary IDFDB002746
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name2-(3,4-Dihydroxyphenyl)-5,6-dihydroxy-7-methoxy-4H-1-benzopyran-4-one
Description2-(3,4-Dihydroxyphenyl)-5,6-dihydroxy-7-methoxy-4H-1-benzopyran-4-one, also known as 3',4',5,6-tetrahydroxy-7-methoxyflavone, belongs to the class of organic compounds known as 7-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C7 atom of the flavonoid backbone. Thus, 2-(3,4-dihydroxyphenyl)-5,6-dihydroxy-7-methoxy-4H-1-benzopyran-4-one is considered to be a flavonoid lipid molecule. 2-(3,4-Dihydroxyphenyl)-5,6-dihydroxy-7-methoxy-4H-1-benzopyran-4-one is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 2-(3,4-Dihydroxyphenyl)-5,6-dihydroxy-7-methoxy-4H-1-benzopyran-4-one has been detected, but not quantified in, fats and oils and sesames. This could make 2-(3,4-dihydroxyphenyl)-5,6-dihydroxy-7-methoxy-4H-1-benzopyran-4-one a potential biomarker for the consumption of these foods.
CAS Number22384-63-0
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
2-(3,4-Dihydroxyphenyl)-5,6-dihydroxy-7-methoxy-4H-chromen-4-oneChEBI
3',4',5,6-Tetrahydroxy-7-methoxyflavoneChEBI
2-(3,4-Dihydroxyphenyl)-5,6-dihydroxy-7-methoxy-4H-1-benzopyran-4-oneChEBI
2-(3,4-Dihydroxyphenyl)-5,6-dihydroxy-7-methoxy-4H-1-benzopyran-4-one, 9ciHMDB
3',4',5,6-Tetrahydroxy-7-methoxy-flavoneHMDB
5,6,3',4'-Tetrahydroxy-7-methoxyflavoneHMDB
2-(3,4-Dihydroxyphenyl)-5,6-dihydroxy-7-methoxy-4H-1-benzopyran-4-one, 9CIdb_source
Flavone, 3',4',5,6-tetrahydroxy-7-methoxy-biospider
Pedalitindb_source
Predicted Properties
PropertyValueSource
Water Solubility0.13 g/LALOGPS
logP2.76ALOGPS
logP2.25ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)8.43ChemAxon
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area116.45 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity81.36 m³·mol⁻¹ChemAxon
Polarizability30.7 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC16H12O7
IUPAC name2-(3,4-dihydroxyphenyl)-5,6-dihydroxy-7-methoxy-4H-chromen-4-one
InChI IdentifierInChI=1S/C16H12O7/c1-22-13-6-12-14(16(21)15(13)20)10(19)5-11(23-12)7-2-3-8(17)9(18)4-7/h2-6,17-18,20-21H,1H3
InChI KeyQWUHUBDKQQPMQG-UHFFFAOYSA-N
Isomeric SMILESCOC1=C(O)C(O)=C2C(=O)C=C(OC2=C1)C1=CC(O)=C(O)C=C1
Average Molecular Weight316.2623
Monoisotopic Molecular Weight316.058302738
Classification
Description Belongs to the class of organic compounds known as 7-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C7 atom of the flavonoid backbone.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassO-methylated flavonoids
Direct Parent7-O-methylated flavonoids
Alternative Parents
Substituents
  • 7-methoxyflavonoid-skeleton
  • 3'-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • Flavone
  • Hydroxyflavonoid
  • 6-hydroxyflavonoid
  • Chromone
  • Benzopyran
  • 1-benzopyran
  • Anisole
  • Catechol
  • Alkyl aryl ether
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Pyranone
  • Benzenoid
  • Pyran
  • Monocyclic benzene moiety
  • Vinylogous acid
  • Heteroaromatic compound
  • Ether
  • Organoheterocyclic compound
  • Oxacycle
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 60.76%; H 3.82%; O 35.41%DFC
Melting PointMp 300-301° dec.DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV Data343 (e 19400) (EtOH) (Berdy)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS2-(3,4-Dihydroxyphenyl)-5,6-dihydroxy-7-methoxy-4H-1-benzopyran-4-one, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00kr-0692000000-a7078c51afe7ad6525f9Spectrum
Predicted GC-MS2-(3,4-Dihydroxyphenyl)-5,6-dihydroxy-7-methoxy-4H-1-benzopyran-4-one, 4 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0a7r-2022090000-1d606be9c93cd3a52156Spectrum
Predicted GC-MS2-(3,4-Dihydroxyphenyl)-5,6-dihydroxy-7-methoxy-4H-1-benzopyran-4-one, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0029000000-0ac125b48c3d61543f382016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0197000000-ec09a1d428fdad7b7b032016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pb9-2790000000-1f82d5b37b3cc55244d42016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0019000000-6a6005e5b8cf1c4c39d72016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0189000000-dab47bf564143865e8472016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4r-6970000000-b41cc1b1bff6867e99f22016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0009000000-d4d9bcf99cd318117dc62021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0009000000-31cd186a85b21b1ec8472021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fk9-0394000000-0cb735aafd2a0ad5b1d62021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0009000000-ad2963bbf6bb0a405a482021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0gi0-0049000000-9abe1832a511678237892021-09-25View Spectrum
NMRNot Available
ChemSpider ID28911
ChEMBL IDCHEMBL476314
KEGG Compound IDC10119
Pubchem Compound ID31161
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB30804
CRC / DFC (Dictionary of Food Compounds) IDCNK17-O:CNK17-O
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDC00003886
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 / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.