Record Information
Version1.0
Creation date2010-04-08 22:11:55 UTC
Update date2015-07-20 23:19:30 UTC
Primary IDFDB015552
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameSinensetin
DescriptionFound in orange peel and other plant sources
CAS Number2306-27-6
Structure
Thumb
Synonyms
SynonymSource
5,6,7,3',4'-PentamethoxyflavoneChEBI
Pedalitin permethyl etherChEBI
2-(3,4-Dimethoxyphenyl)-5,6,7-trimethoxy-4H-1-benzopyran-4-oneHMDB
2-(3,4-Dimethoxyphenyl)-5,6,7-trimethoxy-4H-chromen-4-oneHMDB
3',4',5,6,7-PentamethoxyflavoneHMDB
Sinensetindb_source
Predicted Properties
PropertyValueSource
Water Solubility0.0085 g/LALOGPS
logP2.98ALOGPS
logP2.18ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)15.28ChemAxon
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area72.45 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity99.29 m³·mol⁻¹ChemAxon
Polarizability38.96 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC20H20O7
IUPAC name2-(3,4-dimethoxyphenyl)-5,6,7-trimethoxy-4H-chromen-4-one
InChI IdentifierInChI=1S/C20H20O7/c1-22-13-7-6-11(8-15(13)23-2)14-9-12(21)18-16(27-14)10-17(24-3)19(25-4)20(18)26-5/h6-10H,1-5H3
InChI KeyLKMNXYDUQXAUCZ-UHFFFAOYSA-N
Isomeric SMILESCOC1=C(OC)C=C(C=C1)C1=CC(=O)C2=C(OC)C(OC)=C(OC)C=C2O1
Average Molecular Weight372.3686
Monoisotopic Molecular Weight372.120902994
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
  • 4p-methoxyflavonoid-skeleton
  • 5-methoxyflavonoid-skeleton
  • 6-methoxyflavonoid-skeleton
  • 7-methoxyflavonoid-skeleton
  • Flavone
  • Chromone
  • O-dimethoxybenzene
  • Dimethoxybenzene
  • Benzopyran
  • 1-benzopyran
  • Phenoxy compound
  • Methoxybenzene
  • Anisole
  • Phenol ether
  • Alkyl aryl ether
  • Pyranone
  • Pyran
  • Benzenoid
  • Monocyclic benzene moiety
  • Vinylogous ester
  • Heteroaromatic compound
  • Ether
  • Organoheterocyclic compound
  • Oxacycle
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxide
  • 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 CompositionC 64.51%; H 5.41%; O 30.08%DFC
Melting PointMp 179° (172-173°)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
ChemSpider ID128491
ChEMBL IDCHEMBL226507
KEGG Compound IDC10186
Pubchem Compound ID145659
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID236
DrugBank IDNot Available
HMDB IDHMDB36633
CRC / DFC (Dictionary of Food Compounds) IDKDD85-Q:KDD89-U
EAFUS IDNot Available
Dr. Duke IDSINENSETIN
BIGG IDNot Available
KNApSAcK IDC00013596
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
fungicide24127 A substance used to destroy fungal pests.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
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— 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.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.