Record Information
Version1.0
Creation date2010-04-08 22:04:40 UTC
Update date2019-11-26 02:55:14 UTC
Primary IDFDB000696
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameIsofraxidin
DescriptionIsofraxidin, also known as 6,8-dimethoxy-7-hydroxycoumarin or 7-hydroxy-6,8-dimethoxy-2h-1-benzopyran-2-one, is a member of the class of compounds known as 7-hydroxycoumarins. 7-hydroxycoumarins are coumarins that contain one or more hydroxyl groups attached to the C7 position the coumarin skeleton. Isofraxidin is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Isofraxidin can be found in muskmelon, tarragon, and watermelon, which makes isofraxidin a potential biomarker for the consumption of these food products. Isofraxidin is a chemical compound found in a variety of plants including Eleutherococcus senticosus .
CAS Number486-21-5
Structure
Thumb
Synonyms
SynonymSource
7-Hydroxy-6,8-dimethoxy-2H-1-benzopyran-2-oneKegg
6,8-Dimethoxy-7-hydroxycoumarinMeSH
Iso-fraxidinMeSH
6,8-Dimethoxy-7-hydroxy-coumarinMeSH
7-Hydroxy-6,8-dimethoxycoumarinMeSH
2H-1- Benzopyran-2-one, 7-hydroxy-6,8-dimethoxy-biospider
2H-1-Benzopyran-2-one, 7-hydroxy-6,8-dimethoxy-biospider
Calycanthogenoldb_source
Coumarin, 7-hydroxy-6,8-dimethoxy-biospider
Isofraxidindb_source
Phytodolordb_source
Umbelliferone, 6,8-dimethoxy-biospider
Predicted Properties
PropertyValueSource
Water Solubility1.57 g/LALOGPS
logP1.8ALOGPS
logP1.16ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)7.77ChemAxon
pKa (Strongest Basic)-4.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area64.99 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity56.46 m³·mol⁻¹ChemAxon
Polarizability21.23 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC11H10O5
IUPAC name7-hydroxy-6,8-dimethoxy-2H-chromen-2-one
InChI IdentifierInChI=1S/C11H10O5/c1-14-7-5-6-3-4-8(12)16-10(6)11(15-2)9(7)13/h3-5,13H,1-2H3
InChI KeyHOEVRHHMDJKUMZ-UHFFFAOYSA-N
Isomeric SMILESCOC1=CC2=C(OC(=O)C=C2)C(OC)=C1O
Average Molecular Weight222.1941
Monoisotopic Molecular Weight222.05282343
Classification
Description Belongs to the class of organic compounds known as 7-hydroxycoumarins. These are coumarins that contain one or more hydroxyl groups attached to the C7 position the coumarin skeleton.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCoumarins and derivatives
Sub ClassHydroxycoumarins
Direct Parent7-hydroxycoumarins
Alternative Parents
Substituents
  • 7-hydroxycoumarin
  • Benzopyran
  • 1-benzopyran
  • Anisole
  • Alkyl aryl ether
  • Pyranone
  • Pyran
  • Benzenoid
  • Heteroaromatic compound
  • Lactone
  • Oxacycle
  • Ether
  • Organoheterocyclic compound
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
OntologyNo ontology term
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 148-149°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV Data342 (e ) (MeOH) (Derep)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0290000000-0bbb60d8d4b11b95b03fSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0390000000-57a9014b08f2bf03ccbfSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0bvj-0910000000-0d7a54c1aec421e19611Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0090000000-66689c72c7e98330efffSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0090000000-0406ea331c48a33ad2d6Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6r-0950000000-b9e71c15f1857b74f698Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDC17480
Pubchem Compound ID5318565
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:BFQ16-C
EAFUS IDNot Available
Dr. Duke IDISOFRAXIDIN
BIGG IDNot Available
KNApSAcK IDC00030527
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 / Bioactivities
DescriptorIDDefinitionReference
aldose reductase inhibitor48550 An EC 1.1.1.* (oxidoreductase acting on donor CH-OH group, NAD(+) or NADP(+) acceptor) inhibitor that interferes with the action of aldehyde reductase (EC 1.1.1.21).DUKE
anti leukemic35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti malarial33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
cancer preventive35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
cholereticDUKE
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).