Record Information
Version1.0
Creation date2010-04-08 22:12:50 UTC
Update date2018-01-25 19:43:11 UTC
Primary IDFDB017112
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameTetramethylquercetin
DescriptionRetusin(ariocarpus), also known as 5-hydroxy-3,7,3',4'-tetramethoxyflavone or 3,7,3',4'-tetra-O-methylquercetin, is a member of the class of compounds known as 7-o-methylated flavonoids. 7-o-methylated flavonoids are flavonoids with methoxy groups attached to the C7 atom of the flavonoid backbone. Thus, retusin(ariocarpus) is considered to be a flavonoid lipid molecule. Retusin(ariocarpus) is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Retusin(ariocarpus) can be found in common oregano and mandarin orange (clementine, tangerine), which makes retusin(ariocarpus) a potential biomarker for the consumption of these food products.
CAS Number1245-15-4
Structure
Thumb
Synonyms
SynonymSource
5-Hydroxy-3,7,3',4'-tetramethoxyflavoneMetaCyc, MeSH
3,7,3',4'-Tetra-O-methylquercetinMetaCyc
2-(3,4-Dimethoxyphenyl)-5-hydroxy-3,7-dimethoxy-4H-1-benzopyran-4-onebiospider
5-Hydroxy-3,3',4',7-tetramethoxyflavonedb_source
Flavone, 5-hydroxy-3,3',4',7-tetramethoxy- (8CI)biospider
Quercetin 3,7,3',4'-tetramethyl etherbiospider
Quercetin 3,7,3',4'-tetramethyletherbiospider
Quercetin tetramethyletherbiospider
Quercetin-3,7,3',4'-tetramethyl etherbiospider
Retusin?db_source
Tetramethylquercetinbiospider
Predicted Properties
PropertyValueSource
Water Solubility0.02 g/LALOGPS
logP3.31ALOGPS
logP2.71ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)8.36ChemAxon
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area83.45 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity95.06 m³·mol⁻¹ChemAxon
Polarizability36.66 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC19H18O7
IUPAC name2-(3,4-dimethoxyphenyl)-5-hydroxy-3,7-dimethoxy-4H-chromen-4-one
InChI IdentifierInChI=1S/C19H18O7/c1-22-11-8-12(20)16-15(9-11)26-18(19(25-4)17(16)21)10-5-6-13(23-2)14(7-10)24-3/h5-9,20H,1-4H3
InChI KeyHHGPYJLEJGNWJA-UHFFFAOYSA-N
Isomeric SMILESCOC1=CC(O)=C2C(=O)C(OC)=C(OC2=C1)C1=CC=C(OC)C(OC)=C1
Average Molecular Weight358.342
Monoisotopic Molecular Weight358.10525293
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
  • 3p-methoxyflavonoid-skeleton
  • 3-methoxyflavonoid-skeleton
  • 4p-methoxyflavonoid-skeleton
  • 7-methoxyflavonoid-skeleton
  • Hydroxyflavonoid
  • Flavone
  • 5-hydroxyflavonoid
  • 3-methoxychromone
  • Chromone
  • 1-benzopyran
  • Benzopyran
  • Dimethoxybenzene
  • O-dimethoxybenzene
  • Anisole
  • Phenoxy compound
  • Phenol ether
  • Methoxybenzene
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Pyranone
  • 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
OntologyShould have ontology for this compound
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 63.68%; H 5.06%; O 31.25%DFC
Melting PointMp 159-160°DFC
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
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0009000000-95e43140d41719d30219View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0009000000-577082fa366951f488dbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01dr-2966000000-bf2e0d3fb4407ec38faaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0009000000-8a5664df7dbdeed5c497View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0029000000-3d02636a4b753879db62View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-02g5-1982000000-9cfa3016640c970c7261View in MoNA
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID5352005
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDHBR39-C:KWF31-K
EAFUS IDNot Available
Dr. Duke IDRETUSIN
BIGG IDNot Available
KNApSAcK IDC00004653
HET 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
antitumor35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
cytotoxic52209 A role played by the molecular entity or part thereof which causes the development of a pathological process.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).