Eupafolin (CHEM024543)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 21:46:28 UTC
Update Date2026-04-06 03:29:03 UTC
Accession NumberCHEM024543
Identification
Common NameEupafolin
ClassSmall Molecule
DescriptionEupafolin, also known as 6-methoxy 5 or 73'4'-tetrahydroxyflavone, is a member of the class of compounds known as 6-o-methylated flavonoids. 6-o-methylated flavonoids are flavonoids with methoxy groups attached to the C6 atom of the flavonoid backbone. Thus, eupafolin is considered to be a flavonoid lipid molecule. Eupafolin is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Eupafolin can be found in common sage, lemon verbena, rosemary, and sesame, which makes eupafolin a potential biomarker for the consumption of these food products.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
NepetinMeSH
2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-6-methoxy-4H-chromen-4-oneMeSH
6-Methoxy 5ChEMBL
73'4'-TetrahydroxyflavoneChEMBL
6-MethoxyluteolinChEMBL
PedaltinChEMBL
Chemical FormulaC16H12O7
Average Molecular Mass316.262 g/mol
Monoisotopic Mass316.058 g/mol
CAS Registry Number520-11-6
IUPAC Name2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-6-methoxy-4H-chromen-4-one
Traditional Namenepetin
SMILESCOC1=C(O)C2=C(OC(=CC2=O)C2=CC=C(O)C(O)=C2)C=C1O
InChI IdentifierInChI=1S/C16H12O7/c1-22-16-11(20)6-13-14(15(16)21)10(19)5-12(23-13)7-2-3-8(17)9(18)4-7/h2-6,17-18,20-21H,1H3
InChI KeyFHHSEFRSDKWJKJ-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as 6-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C6 atom of the flavonoid backbone.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassO-methylated flavonoids
Direct Parent6-O-methylated flavonoids
Alternative Parents
Substituents
  • 6-methoxyflavonoid-skeleton
  • 7-hydroxyflavonoid
  • 3'-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • Flavone
  • Hydroxyflavonoid
  • Chromone
  • Benzopyran
  • 1-benzopyran
  • Anisole
  • Catechol
  • Alkyl aryl ether
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Pyranone
  • Benzenoid
  • Pyran
  • Monocyclic benzene moiety
  • Vinylogous acid
  • Heteroaromatic compound
  • Ether
  • Organoheterocyclic compound
  • Oxacycle
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.12 g/LALOGPS
logP2.75ALOGPS
logP2.25ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)7.09ChemAxon
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area116.45 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity81.36 m³·mol⁻¹ChemAxon
Polarizability30.8 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00ks-0593000000-d04df03ef923f105cbb2Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-0ug0-0792000000-b0493b07c4cff8abe96dSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-0ug0-0792000000-b0493b07c4cff8abe96dSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-0ug0-0792000000-b0493b07c4cff8abe96dSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 50V, Negativesplash10-001r-0940000000-5baa8bd5a625567f08ddSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT 22V, positivesplash10-0udi-0009000000-f37db28495a264cf9503Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT 22V, positivesplash10-0udi-0009000000-6cb654a8d44da14a1c4bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0029000000-48a42a678280a96feb08Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0169000000-c3695b331b8399faf052Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4m-3960000000-b179e1b189656ec5854bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0009000000-d1eea835c66835196377Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0169000000-5a4afa1d2dc63c754c00Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-5950000000-10104b78aa48595ecdf7Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0150804
FooDB IDFDB002422
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID5317284
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available