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Showing Compound Sinensetin (FDB015552)

Record Information
Version1.0
Creation date2010-04-08 22:11:55 UTC
Update date2025-11-19 00:56:04 UTC
Primary IDFDB015552
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameSinensetin
DescriptionSinensetin 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, sinensetin is considered to be a flavonoid. Sinensetin is a bitter tasting compound. Sinensetin is found, on average, in the highest concentration within sweet oranges (Citrus sinensis). Sinensetin has also been detected, but not quantified in, several different foods, such as citrus, grapefruits (Citrus X paradisi), mandarin orange (clementine, tangerine), and rosemaries (Rosmarinus officinalis). This could make sinensetin a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Sinensetin.
CAS Number2306-27-6
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
5,6,7,3',4'-PentamethoxyflavoneChEBI
Pedalitin permethyl etherChEBI
3',4',5,6,7-PentamethoxyflavoneMeSH
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
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
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
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Role

Biological role:

Physico-Chemical Properties
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
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSSinensetin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-052f-0329000000-4a86676038deb509621eSpectrum
Predicted GC-MSSinensetin, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSSinensetin, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-08i0-0149000000-bb6b23311e4ce206caa42017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0btc-0009000000-b1b4ebfd1015e7c3e8322017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0btc-0009000000-4613a2f05d4ac45d4d0a2017-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0009000000-92007689580e0fd2a93a2016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0009000000-983639cfb968be7ff9e72016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03du-1489000000-8f1702061faef57a06292016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0009000000-0155e9190c7fbbd16deb2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0009000000-07fcbf4b8a2cdf9787642016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-056r-0292000000-9d41a9720482d2978a6b2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0009000000-aa9385dbb205bb238b882021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0009000000-005119c3fd0ac1eff9592021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-06ur-0109000000-7d76eea4f22c84fab2de2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0009000000-cef598d38b8dbae9b6612021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05i0-0009000000-f174bc75cf6bee81dbda2021-09-24View Spectrum
NMRNot Available
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
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDSinensetin
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 An agent that kills or inhibits the growth of fungi, playing a biological role in preventing fungal infections. Therapeutically, it is used to treat fungal diseases, with key medical applications including athlete's foot, ringworm, and candidiasis, as well as agricultural uses to protect crops from fungal damage.DUKE
Pesticide25944 An agent that kills or repels pests, playing a biological role in controlling insect, weed, and fungal populations. Therapeutically, pesticides have limited applications, but some are used to treat ectoparasitic infestations, such as lice and scabies. Key medical uses include topical treatments for head lice and scabies, highlighting their role in managing parasitic infections.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.