Record Information
Version1.0
Creation date2010-04-08 22:05:30 UTC
Update date2018-05-28 22:42:05 UTC
Primary IDFDB002731
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameDihydromethysticin
DescriptionIsolated from Piper methysticum (kava). FDA advises against use of kava in food due to potential risk of severe liver damage (2002) Dihydromethysticin is one of the six major kavalactones found in the kava plant.
CAS Number19902-91-1
Structure
Thumb
Synonyms
SynonymSource
(+)-DihydromethysticinHMDB
7,8-Dihydro-methysticinHMDB
7,8-DihydromethysticinHMDB
DHMHMDB
PseudomethysticinHMDB
Y-methysticinHMDB
(+)-dihydromethysticinbiospider
7,8-dihydro-MethysticinHMDB
Dihydromethysticindb_source
Dihydromethysticin (van)biospider
Methysticin, 7,8-dihydro-biospider
y-Methysticindb_source
Predicted Properties
PropertyValueSource
Water Solubility0.091 g/LALOGPS
logP2.13ALOGPS
logP2.18ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)16.43ChemAxon
pKa (Strongest Basic)-4.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area53.99 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity72.16 m³·mol⁻¹ChemAxon
Polarizability28.79 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC15H16O5
IUPAC name6-[2-(2H-1,3-benzodioxol-5-yl)ethyl]-4-methoxy-5,6-dihydro-2H-pyran-2-one
InChI IdentifierInChI=1S/C15H16O5/c1-17-12-7-11(20-15(16)8-12)4-2-10-3-5-13-14(6-10)19-9-18-13/h3,5-6,8,11H,2,4,7,9H2,1H3
InChI KeyRSIWXFIBHXYNFM-UHFFFAOYSA-N
Isomeric SMILESCOC1=CC(=O)OC(CCC2=CC3=C(OCO3)C=C2)C1
Average Molecular Weight276.2845
Monoisotopic Molecular Weight276.099773622
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
  • Benzodioxole
  • Dihydropyranone
  • Pyran
  • Benzenoid
  • Enoate ester
  • Vinylogous ester
  • Alpha,beta-unsaturated carboxylic ester
  • Carboxylic acid ester
  • Lactone
  • Monocarboxylic acid or derivatives
  • Acetal
  • Carboxylic acid derivative
  • Oxacycle
  • Organoheterocyclic compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 65.21%; H 5.84%; O 28.95%DFC
Melting PointMp 117-118°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]D +21 (MeOH)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
ChemSpider ID200147
ChEMBL IDNot Available
KEGG Compound IDC09926
Pubchem Compound ID229852
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB30791
CRC / DFC (Dictionary of Food Compounds) IDHGJ61-Y:CNH47-I
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDC00002988
HET IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDDihydromethysticin
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