Record Information
Version1.0
Creation date2010-04-08 22:10:15 UTC
Update date2020-02-24 19:11:08 UTC
Primary IDFDB012577
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameFraxidin
DescriptionFraxidin, also known as 8-hydroxy-6,7-dimethoxy-2h-1-benzopyran-2-one, is a member of the class of compounds known as hydroxycoumarins. Hydroxycoumarins are coumarins that contain one or more hydroxyl groups attached to the coumarin skeleton. Fraxidin is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Fraxidin can be found in durian and watermelon, which makes fraxidin a potential biomarker for the consumption of these food products.
CAS Number525-21-3
Structure
Thumb
Synonyms
SynonymSource
8-Hydroxy-6,7-dimethoxy-2H-1-benzopyran-2-oneKegg
FraxidenMeSH
2H-1-Benzopyran-2-one, 8-hydroxy-6,7-dimethoxy-biospider
8-Hydroxy-6,7-dimethoxy-2-benzopyronebiospider
8-Hydroxy-6,7-dimethoxycoumarindb_source
Fraxidindb_source
Predicted Properties
PropertyValueSource
Water Solubility1.58 g/LALOGPS
logP1.83ALOGPS
logP1.81ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)10.73ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area64.99 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity56.46 m³·mol⁻¹ChemAxon
Polarizability21.2 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC11H10O5
IUPAC name8-hydroxy-6,7-dimethoxy-2H-chromen-2-one
InChI IdentifierInChI=1S/C11H10O5/c1-14-7-5-6-3-4-8(12)16-10(6)9(13)11(7)15-2/h3-5,13H,1-2H3
InChI KeyQNFBKOHHLAWWTC-UHFFFAOYSA-N
Isomeric SMILESCOC1=C(OC)C(O)=C2OC(=O)C=CC2=C1
Average Molecular Weight222.1941
Monoisotopic Molecular Weight222.05282343
Classification
Description Belongs to the class of organic compounds known as hydroxycoumarins. These are coumarins that contain one or more hydroxyl groups attached to the coumarin skeleton.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCoumarins and derivatives
Sub ClassHydroxycoumarins
Direct ParentHydroxycoumarins
Alternative Parents
Substituents
  • Hydroxycoumarin
  • Benzopyran
  • 1-benzopyran
  • Anisole
  • 1-hydroxy-4-unsubstituted benzenoid
  • Alkyl aryl ether
  • Pyranone
  • Benzenoid
  • Pyran
  • Heteroaromatic compound
  • Lactone
  • Ether
  • Oxacycle
  • Organoheterocyclic compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Source:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 59.46%; H 4.54%; O 36.00%DFC
Melting PointMp 196-197°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-MSFraxidin, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0fmi-1090000000-57a4b8a1ffc02d3ff38cSpectrum
Predicted GC-MSFraxidin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0006-0920000000-0789ab666a899a6ee191Spectrum
Predicted GC-MSFraxidin, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0090000000-d072371fa1a0d12b8a302016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0190000000-6a957c893a8bc14e1b832016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-06tf-1920000000-4e0154f5381d381b37662016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0290000000-130b68560aefb7723b5f2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0490000000-12c022694af4770c20c82016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052e-3900000000-7b9037a7fee8191988242016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0090000000-b3900c5041b4d10c4c652021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0290000000-668671f6655792921d732021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000b-3900000000-e8ea2de535bfedabeb302021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0090000000-cf583f8087451ddaae0f2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0190000000-684c8c34647b0cdb11a32021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-2900000000-c927504b30b3573647e42021-09-22View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDC17479
Pubchem Compound ID3083616
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDBFQ13-Z:HJC23-A
EAFUS IDNot Available
Dr. Duke IDFRAXIDIN
BIGG IDNot Available
KNApSAcK IDC00019875
HET IDNot Available
Food Biomarker OntologyNot Available
VMH 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— 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.