Dihydromethysticin (CHEM024808)

Record Information
Version1.0
Creation Date2016-05-25 21:56:23 UTC
Update Date2026-08-19 10:30:53 UTC
Accession NumberCHEM024808
Identification
Common NameDihydromethysticin
ClassSmall Molecule
Description
Dihydromethysticin is found in beverages. Dihydromethysticin is isolated 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
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(+)-DihydromethysticinHMDB
7,8-Dihydro-methysticinHMDB
7,8-DihydromethysticinHMDB
DHMHMDB
PseudomethysticinHMDB
Y-methysticinHMDB
Chemical FormulaC15H16O5
Average Molecular Mass276.285 g/mol
Monoisotopic Mass276.100 g/mol
CAS Registry Number19902-91-1
IUPAC Name6-[2-(2H-1,3-benzodioxol-5-yl)ethyl]-4-methoxy-5,6-dihydro-2H-pyran-2-one
Traditional Namedihydromethysticin
SMILESCOC1=CC(=O)OC(CCC2=CC3=C(OCO3)C=C2)C1
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
Chemical Taxonomy
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
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 Solubility0.091 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
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
External Links
DrugBank IDNot Available
HMDB IDHMDB0030791
FooDB IDFDB002731
Phenol Explorer IDNot Available
KNApSAcK IDC00002988
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkDihydromethysticin
Chemspider ID200147
ChEBI ID1034670
PubChem Compound ID229852
Kegg Compound IDC09926
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Hu L, Jhoo JW, Ang CY, Dinovi M, Mattia A: Determination of six kavalactones in dietary supplements and selected functional foods containing Piper methysticum by isocratic liquid chromatography with internal standard. J AOAC Int. 2005 Jan-Feb;88(1):16-25.
2. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.