Record Information
Version1.0
Creation date2010-04-08 22:04:29 UTC
Update date2018-01-25 19:27:13 UTC
Primary IDFDB000219
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name3-Methoxysinensetin
Description3-methoxysinensetin, also known as 35673'4'-hexamethoxyflavone, 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, 3-methoxysinensetin is considered to be a flavonoid lipid molecule. 3-methoxysinensetin is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). 3-methoxysinensetin can be found in grapefruit and sweet orange, which makes 3-methoxysinensetin a potential biomarker for the consumption of these food products.
CAS Number1251-84-9
Structure
Thumb
Synonyms
SynonymSource
35673'4'-HexamethoxyflavoneHMDB
2-(3,4-Dimethoxyphenyl)-3,5,6,7-tetramethoxy-4H-1-benzopyran-4-oneHMDB
3,3',4',5,6,7-HexamethoxyflavoneHMDB
AurantinHMDB
Oxyayanin b trimethyl etherHMDB
Quercetagetin hexamethyl etherHMDB
3,5,6,7-Tetrahydroxy-2-(3,4-dihydroxyphenyl)-4H-1-benzopyran-4-oneMeSH
QuercetogetinMeSH
3,5,6,7,3',4'-HexamethoxyflavoneMeSH
QuercetagetinMeSH
Predicted Properties
PropertyValueSource
Water Solubility0.0099 g/LALOGPS
logP2.51ALOGPS
logP2.05ChemAxon
logS-4.6ALOGPS
pKa (Strongest Basic)-4.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area81.68 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity106.01 m³·mol⁻¹ChemAxon
Polarizability41.76 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC21H22O8
IUPAC name2-(3,4-dimethoxyphenyl)-3,5,6,7-tetramethoxy-4H-chromen-4-one
InChI IdentifierInChI=1S/C21H22O8/c1-23-12-8-7-11(9-13(12)24-2)18-21(28-6)17(22)16-14(29-18)10-15(25-3)19(26-4)20(16)27-5/h7-10H,1-6H3
InChI KeyCHXSDKWBSFDZEU-UHFFFAOYSA-N
Isomeric SMILESCOC1=C(OC)C=C(C=C1)C1=C(OC)C(=O)C2=C(OC)C(OC)=C(OC)C=C2O1
Average Molecular Weight402.3946
Monoisotopic Molecular Weight402.13146768
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
  • 5-methoxyflavonoid-skeleton
  • 6-methoxyflavonoid-skeleton
  • 7-methoxyflavonoid-skeleton
  • Flavone
  • 3-methoxychromone
  • Chromone
  • 1-benzopyran
  • Benzopyran
  • O-dimethoxybenzene
  • Dimethoxybenzene
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Phenol ether
  • Alkyl aryl ether
  • Pyranone
  • Pyran
  • Benzenoid
  • Monocyclic benzene moiety
  • Vinylogous ester
  • Heteroaromatic compound
  • Ether
  • Organoheterocyclic compound
  • Oxacycle
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
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
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00dr-0209000000-89ee0137b28b099b97c5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-052r-0139000000-f5180351533ec1611489View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0079-0009000000-7eaf9eb53dd67dcae352View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0079-0009000000-dced3ea69b5ec76a817fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0000900000-a6c74af03ee0c68c56ebView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0001900000-a449fc7e55cd5473f60cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0459-1369000000-6b3437d1d4b5a6f1d321View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0000900000-b843ea9ef34455b13bbaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0006900000-73d46ab8f7dba97ef6edView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4u-1897000000-c3675d0285953cd49421View in MoNA
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID393
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
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 / 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— Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.