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Showing Compound Quercetin 3-O-methyl-ether (FDB006540)

Record Information
Version1.0
Creation date2010-04-08 22:07:11 UTC
Update date2019-11-26 03:01:10 UTC
Primary IDFDB006540
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameQuercetin 3-O-methyl-ether
DescriptionQuercetin 3-methyl ether, also known as 3',4',5,7-tetrahydroxy-3-methoxyflavone or isorhamnetin, is a member of the class of compounds known as 3-o-methylated flavonoids. 3-o-methylated flavonoids are flavonoids with methoxy groups attached to the C3 atom of the flavonoid backbone. Thus, quercetin 3-methyl ether is considered to be a flavonoid lipid molecule. Quercetin 3-methyl ether is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Quercetin 3-methyl ether can be synthesized from quercetin. Quercetin 3-methyl ether can also be synthesized into 3-O-methylquercetin 7-O-beta-glucopyranosyl-4'-O-beta-D-glucopyranoside. Quercetin 3-methyl ether can be found in common bean, which makes quercetin 3-methyl ether a potential biomarker for the consumption of this food product.
CAS Number1486-70-0
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-3-methoxy-4H-1-benzopyran-4-oneChEBI
3-Methoxy-5,7,3',4'-tetrahydroxyflavoneChEBI
3-O-MethylquercetinChEBI
3',4',5,7-Tetrahydroxy-3-methoxyflavoneKegg
3,4',5,7-Tetrahydroxy-3'-methoxyflavoneMeSH
Iso-rhamnetinMeSH
IsorhamnetineMeSH
3-Methyl-quercetinMeSH
IsorhamnetinMeSH
3,4',5,7-Tetrahydroxy-3'-methoxy-flavoneMeSH
3-MethylquercetinMeSH
Predicted Properties
PropertyValueSource
Water Solubility0.14 g/LALOGPS
logP2.68ALOGPS
logP2.27ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)6.38ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area116.45 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity81.61 m³·mol⁻¹ChemAxon
Polarizability30.49 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC16H12O7
IUPAC name2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-methoxy-4H-chromen-4-one
InChI IdentifierInChI=1S/C16H12O7/c1-22-16-14(21)13-11(20)5-8(17)6-12(13)23-15(16)7-2-3-9(18)10(19)4-7/h2-6,17-20H,1H3
InChI KeyWEPBGSIAWZTEJR-UHFFFAOYSA-N
Isomeric SMILESCOC1=C(OC2=CC(O)=CC(O)=C2C1=O)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 3-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C3 atom of the flavonoid backbone.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassO-methylated flavonoids
Direct Parent3-O-methylated flavonoids
Alternative Parents
Substituents
  • 3-methoxyflavonoid-skeleton
  • Hydroxyflavonoid
  • Flavone
  • 3'-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • 3-methoxychromone
  • Chromone
  • Benzopyran
  • 1-benzopyran
  • Catechol
  • 1-hydroxy-4-unsubstituted benzenoid
  • Pyranone
  • Phenol
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Monocyclic benzene moiety
  • Benzenoid
  • Pyran
  • Vinylogous acid
  • Heteroaromatic compound
  • Organoheterocyclic compound
  • Oxacycle
  • Ether
  • Organic oxide
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • 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 CompositionNot Available
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 DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSQuercetin 3-O-methyl-ether, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-000i-0592000000-adb64153ab382927fa9cSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0019000000-6e26aedd5891d352be572016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0269000000-3130de6aab38497a6b592016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0zfr-8890000000-7202f7ddb6a2ddc52e392016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0009000000-056f788e0a1b8961e4612016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0159000000-8d092e900b4a2bcd1f692016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0j5j-4950000000-69349126db13997c53f72016-08-03View 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 IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDQUERCETIN-3-O-METHYL-ETHER
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
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 inflammatory35472 A substance that reduces or suppresses inflammation.DUKE
anti rhinoviral22587 A substance that destroys or inhibits replication of viruses.DUKE
anti viral22587 A substance that destroys or inhibits replication of viruses.DUKE
cancer preventive35610 A substance that inhibits or prevents the proliferation of neoplasms.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
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
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).