Record Information
Version1.0
Creation date2010-04-08 22:10:09 UTC
Update date2015-07-20 22:50:01 UTC
Primary IDFDB012419
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameYangonin
DescriptionFound in kava root (Piper methysticum). FDA advises against use of kava in food due to potential risk of severe liver damage (2002)
CAS Number500-62-9
Structure
Thumb
Synonyms
SynonymSource
4-Methoxy-6-[2-(4-methoxyphenyl)ethenyl]-2H-pyran-2-oneKegg
4-Methoxy-6-(4-methoxystyryl)-a-pyroneHMDB
4-Methoxy-6-(beta-(p-anisyl)vinyl)-alpha-pyroneHMDB
4-Methoxy-6-(p-methoxystyryl)-2H-pyran-2-oneHMDB
4-Methoxy-6-[(e)-2-(4-methoxyphenyl)vinyl]-2H-pyran-2-oneHMDB
4-Methoxy-6-[2-(4-methoxyphenyl)ethenyl]-2H-pyran-2-one, 9ciHMDB
2H-Pyran-2-one, 4-methoxy-6-(p-methoxystyryl)-biospider
4-methoxy-6-[(E)-2-(4-methoxyphenyl)vinyl]-2H-pyran-2-onebiospider
4-Methoxy-6-[2-(4-methoxyphenyl)ethenyl]-2H-pyran-2-one, 9CIdb_source
Predicted Properties
PropertyValueSource
Water Solubility0.013 g/LALOGPS
logP3ALOGPS
logP2.48ChemAxon
logS-4.3ALOGPS
pKa (Strongest Basic)-4.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area44.76 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity75.2 m³·mol⁻¹ChemAxon
Polarizability27.58 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC15H14O4
IUPAC name4-methoxy-6-[(E)-2-(4-methoxyphenyl)ethenyl]-2H-pyran-2-one
InChI IdentifierInChI=1S/C15H14O4/c1-17-12-6-3-11(4-7-12)5-8-13-9-14(18-2)10-15(16)19-13/h3-10H,1-2H3/b8-5+
InChI KeyXLHIYUYCSMZCCC-VMPITWQZSA-N
Isomeric SMILESCOC1=CC=C(\C=C\C2=CC(OC)=CC(=O)O2)C=C1
Average Molecular Weight258.2693
Monoisotopic Molecular Weight258.089208936
Classification
Description belongs to the class of organic compounds known as kavalactones. These are lactones, which is structurally characterized by a benzene ring and a pyranone moiety, linked to each other to form a 4-methoxy-6-(2-phenylethyl)-2H-pyran-2-one skeleton.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassKavalactones
Sub ClassNot Available
Direct ParentKavalactones
Alternative Parents
Substituents
  • Kavalactone
  • Anisole
  • Phenoxy compound
  • Phenol ether
  • Styrene
  • Methoxybenzene
  • Pyranone
  • Alkyl aryl ether
  • Benzenoid
  • Monocyclic benzene moiety
  • Pyran
  • Vinylogous ester
  • Heteroaromatic compound
  • Lactone
  • Ether
  • Organoheterocyclic compound
  • Oxacycle
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 69.76%; H 5.46%; O 24.78%DFC
Melting PointMp 153-154°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
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-052f-1390000000-b5bbf1f136609500165bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0090000000-0064fe61f04f340cfc41View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0390000000-02f5c4ac24041bff5138View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-2950000000-c356024333a2fa73d48fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0090000000-c80037a5499d4ee96e80View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-8190000000-25a283ee23eb1eaea784View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9810000000-a91c0a22e3459308740cView in MoNA
ChemSpider ID4444896
ChEMBL IDCHEMBL1098658
KEGG Compound IDC09980
Pubchem Compound ID5281575
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB34144
CRC / DFC (Dictionary of Food Compounds) IDHGT99-N:HGT99-N
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDC00003024
HET IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDYangonin
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