You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:38:54 UTC
Update Date2019-07-23 06:07:14 UTC
HMDB IDHMDB0030766
Secondary Accession Numbers
  • HMDB30766
Metabolite Identification
Common Name11-Hydroxy-12-methoxydihydrokawain
Description11-Hydroxy-12-methoxydihydrokawain is found in beverages. 11-Hydroxy-12-methoxydihydrokawain is a constituent of Piper methysticum (kava). FDA advises against use of kava in food due to potential risk of severe liver damage (2002)
Structure
Data?1563862034
Synonyms
ValueSource
11-Hydroxy-12-methoxydihydrokavainHMDB
4-Methoxy-6-[2-(3-hydroxy-4-methoxyphenyl)ethyl]-5,6-dihydro-2H-pyran-2-oneHMDB
Chemical FormulaC15H18O5
Average Molecular Weight278.3004
Monoisotopic Molecular Weight278.115423686
IUPAC Name6-[2-(3-hydroxy-4-methoxyphenyl)ethyl]-4-methoxy-5,6-dihydro-2H-pyran-2-one
Traditional Name6-[2-(3-hydroxy-4-methoxyphenyl)ethyl]-4-methoxy-5,6-dihydropyran-2-one
CAS Registry Number38146-59-7
SMILES
COC1=CC(=O)OC(CCC2=CC(O)=C(OC)C=C2)C1
InChI Identifier
InChI=1S/C15H18O5/c1-18-12-8-11(20-15(17)9-12)5-3-10-4-6-14(19-2)13(16)7-10/h4,6-7,9,11,16H,3,5,8H2,1-2H3
InChI KeyQQLVNWDQIUZGJM-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound 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
  • Methoxyphenol
  • Phenoxy compound
  • Anisole
  • Phenol ether
  • Methoxybenzene
  • Alkyl aryl ether
  • 1-hydroxy-4-unsubstituted benzenoid
  • Dihydropyranone
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Benzenoid
  • Monocyclic benzene moiety
  • Pyran
  • Vinylogous ester
  • Enoate ester
  • Alpha,beta-unsaturated carboxylic ester
  • Lactone
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Ether
  • Carboxylic acid derivative
  • Oxacycle
  • Organoheterocyclic compound
  • Carbonyl group
  • Organic oxide
  • Organooxygen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point165 - 167 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.11 g/LALOGPS
logP2.17ALOGPS
logP2.09ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)9.9ChemAxon
pKa (Strongest Basic)-4.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area64.99 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity74.84 m³·mol⁻¹ChemAxon
Polarizability29.25 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-052r-4950000000-6e36607046ee12d070d0JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0abl-9486000000-5c6c8da93d149916b48bJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0390000000-670c9eb8b6aa4fde42b0JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01t9-1930000000-4e3f0a6852806702f386JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fi0-6900000000-3c1115a3db24bb00c2b4JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0090000000-94c59b567aeb4e06ced5JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0059-2190000000-361abb061c78195881f4JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0536-9560000000-becf68791ede74160560JSpectraViewer | MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB002701
KNApSAcK IDC00029378
Chemspider ID509813
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound586508
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Enzymes

General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Reactions
11-Hydroxy-12-methoxydihydrokawain → 3,4,5-trihydroxy-6-{2-methoxy-5-[2-(4-methoxy-6-oxo-3,6-dihydro-2H-pyran-2-yl)ethyl]phenoxy}oxane-2-carboxylic aciddetails
General function:
sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of phenolic monoamines (neurotransmitters such as dopamine, norepinephrine and serotonin) and phenolic and catechol drugs.
Gene Name:
SULT1A3
Uniprot ID:
P0DMM9
Molecular weight:
34195.96
Reactions
11-Hydroxy-12-methoxydihydrokawain → {2-methoxy-5-[2-(4-methoxy-6-oxo-3,6-dihydro-2H-pyran-2-yl)ethyl]phenyl}oxidanesulfonic aciddetails