Record Information
Version1.0
Creation date2010-04-08 22:06:34 UTC
Update date2020-02-24 19:11:08 UTC
Primary IDFDB005199
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameIsoscopoletin
DescriptionIsoscopoletin, also known as 6-hydroxy-7-methoxycoumarin or 7-methoxyesculetin, 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. Isoscopoletin is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Isoscopoletin can be found in coriander and eggplant, which makes isoscopoletin a potential biomarker for the consumption of these food products.
CAS Number776-86-3
Structure
Thumb
Synonyms
SynonymSource
IsoscopoletineHMDB
6-Hydroxy-7-methoxycoumarinMeSH
2H-1-Benzopyran-2-one, 6-hydroxy-7-methoxy-biospider
6-Hydroxy-7-methoxy-2-benzopyronebiospider
7-Methoxyesculetinbiospider
7-Methyl esculetinbiospider
Esculetin 7-methyl etherbiospider
Isoscopoletinbiospider
Predicted Properties
PropertyValueSource
Water Solubility2.35 g/LALOGPS
logP1.65ALOGPS
logP1.32ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)9.84ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area55.76 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity49.99 m³·mol⁻¹ChemAxon
Polarizability18.31 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC10H8O4
IUPAC name6-hydroxy-7-methoxy-2H-chromen-2-one
InChI IdentifierInChI=1S/C10H8O4/c1-13-9-5-8-6(4-7(9)11)2-3-10(12)14-8/h2-5,11H,1H3
InChI KeySYTYLPHCLSSCOJ-UHFFFAOYSA-N
Isomeric SMILESCOC1=C(O)C=C2C=CC(=O)OC2=C1
Average Molecular Weight192.1681
Monoisotopic Molecular Weight192.042258744
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-2-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 CompositionNot Available
Melting PointNot Available
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-MSIsoscopoletin, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00di-4390000000-fccf088f63f3c39a0659Spectrum
Predicted GC-MSIsoscopoletin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-01ot-0900000000-b2d5f9be748456ebc9f8Spectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0900000000-cb18a327921677779132Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-0900000000-e6ddfda18fb3a8756f45Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-003l-3900000000-03641f5054cbf0fba188Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0900000000-b4b39cf8fa2a3746bc86Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0900000000-9384e4070c02e1332b3aSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0059-1900000000-33da37c1b1f77abae651Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID69894
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDISOSCOPOLETIN
BIGG IDNot Available
KNApSAcK IDC00039452
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
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).