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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 21:47:45 UTC
Update Date2022-03-07 02:55:00 UTC
HMDB IDHMDB0036633
Secondary Accession Numbers
  • HMDB36633
Metabolite Identification
Common 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. Sinensetin is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review very few articles have been published on Sinensetin.
Structure
Data?1563862900
Synonyms
ValueSource
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
Chemical FormulaC20H20O7
Average Molecular Weight372.3686
Monoisotopic Molecular Weight372.120902994
IUPAC Name2-(3,4-dimethoxyphenyl)-5,6,7-trimethoxy-4H-chromen-4-one
Traditional Namesinensetin
CAS Registry Number2306-27-6
SMILES
COC1=C(OC)C=C(C=C1)C1=CC(=O)C2=C(OC)C(OC)=C(OC)C=C2O1
InChI Identifier
InChI=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
Chemical Taxonomy
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
Physiological effect
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point179 °CNot Available
Boiling Point547.00 to 548.00 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility24.04 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP2.634 (est)The Good Scents Company Information System
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Not Available186.413http://allccs.zhulab.cn/database/detail?ID=AllCCS00001483
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+190.60131661259
DarkChem[M-H]-191.78131661259
DeepCCS[M+H]+183.32630932474
DeepCCS[M-H]-180.96830932474
DeepCCS[M-2H]-215.0430932474
DeepCCS[M+Na]+190.26830932474
AllCCS[M+H]+187.732859911
AllCCS[M+H-H2O]+184.632859911
AllCCS[M+NH4]+190.632859911
AllCCS[M+Na]+191.432859911
AllCCS[M-H]-192.032859911
AllCCS[M+Na-2H]-192.032859911
AllCCS[M+HCOO]-192.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
SinensetinCOC1=C(OC)C=C(C=C1)C1=CC(=O)C2=C(OC)C(OC)=C(OC)C=C2O14719.4Standard polar33892256
SinensetinCOC1=C(OC)C=C(C=C1)C1=CC(=O)C2=C(OC)C(OC)=C(OC)C=C2O13263.8Standard non polar33892256
SinensetinCOC1=C(OC)C=C(C=C1)C1=CC(=O)C2=C(OC)C(OC)=C(OC)C=C2O13355.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Sinensetin GC-MS (Non-derivatized) - 70eV, Positivesplash10-052f-0329000000-4a86676038deb509621e2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Sinensetin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Sinensetin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Sinensetin Linear Ion Trap , negative-QTOFsplash10-08i0-0149000000-bb6b23311e4ce206caa42017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sinensetin Linear Ion Trap , positive-QTOFsplash10-0btc-0009000000-b1b4ebfd1015e7c3e8322017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sinensetin Linear Ion Trap , positive-QTOFsplash10-0btc-0009000000-4613a2f05d4ac45d4d0a2017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sinensetin 10V, Positive-QTOFsplash10-00di-0009000000-92007689580e0fd2a93a2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sinensetin 20V, Positive-QTOFsplash10-00di-0009000000-983639cfb968be7ff9e72016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sinensetin 40V, Positive-QTOFsplash10-03du-1489000000-8f1702061faef57a06292016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sinensetin 10V, Negative-QTOFsplash10-00di-0009000000-0155e9190c7fbbd16deb2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sinensetin 20V, Negative-QTOFsplash10-00di-0009000000-07fcbf4b8a2cdf9787642016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sinensetin 40V, Negative-QTOFsplash10-056r-0292000000-9d41a9720482d2978a6b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sinensetin 10V, Positive-QTOFsplash10-00di-0009000000-aa9385dbb205bb238b882021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sinensetin 20V, Positive-QTOFsplash10-00di-0009000000-005119c3fd0ac1eff9592021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sinensetin 40V, Positive-QTOFsplash10-06ur-0109000000-7d76eea4f22c84fab2de2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sinensetin 10V, Negative-QTOFsplash10-00di-0009000000-cef598d38b8dbae9b6612021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sinensetin 20V, Negative-QTOFsplash10-05i0-0009000000-f174bc75cf6bee81dbda2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound ID236
FooDB IDFDB015552
KNApSAcK IDC00013596
Chemspider ID128491
KEGG Compound IDC10186
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkSinensetin
METLIN IDNot Available
PubChem Compound145659
PDB IDNot Available
ChEBI ID9159
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1637341
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .