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 17:37:33 UTC
Update Date2019-07-23 06:06:42 UTC
HMDB IDHMDB0030549
Secondary Accession Numbers
  • HMDB30549
Metabolite Identification
Common Name5,6-Dihydro-4-methoxy-6-[2-(4-methoxyphenyl)ethyl]-2H-pyran-2-one
Description5,6-Dihydro-4-methoxy-6-[2-(4-methoxyphenyl)ethyl]-2H-pyran-2-one, also known as 5,6,7,8-tetrahydroyangonin, 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. 5,6-Dihydro-4-methoxy-6-[2-(4-methoxyphenyl)ethyl]-2H-pyran-2-one is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 5,6-Dihydro-4-methoxy-6-[2-(4-methoxyphenyl)ethyl]-2H-pyran-2-one has been detected, but not quantified in, beverages. This could make 5,6-dihydro-4-methoxy-6-[2-(4-methoxyphenyl)ethyl]-2H-pyran-2-one a potential biomarker for the consumption of these foods.
Structure
Data?1563862002
Synonyms
ValueSource
5,6,7,8-TetrahydroyangoninHMDB
Chemical FormulaC15H18O4
Average Molecular Weight262.301
Monoisotopic Molecular Weight262.120509064
IUPAC Name4-methoxy-6-[2-(4-methoxyphenyl)ethyl]-5,6-dihydro-2H-pyran-2-one
Traditional Name4-methoxy-6-[2-(4-methoxyphenyl)ethyl]-5,6-dihydropyran-2-one
CAS Registry Number49776-58-1
SMILES
COC1=CC(=O)OC(CCC2=CC=C(OC)C=C2)C1
InChI Identifier
InChI=1S/C15H18O4/c1-17-12-6-3-11(4-7-12)5-8-13-9-14(18-2)10-15(16)19-13/h3-4,6-7,10,13H,5,8-9H2,1-2H3
InChI KeyIZGFAKZIDOQLHS-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
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Phenol ether
  • Alkyl aryl ether
  • Dihydropyranone
  • Monocyclic benzene moiety
  • Benzenoid
  • Pyran
  • Vinylogous ester
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Carboxylic acid ester
  • Lactone
  • Organoheterocyclic compound
  • Ether
  • Oxacycle
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point89 - 90 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.04 g/LALOGPS
logP2.87ALOGPS
logP2.4ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)16.43ChemAxon
pKa (Strongest Basic)-4.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area44.76 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity72.86 m³·mol⁻¹ChemAxon
Polarizability28.51 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-05fr-5950000000-8a3df98cf6c112a79d66Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0290000000-d73f7cd4a10407119183Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01ot-1930000000-8271e8b3696d4038830aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pb9-4900000000-f1677005f630a2241c00Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0090000000-a5b52057c6bf7fb41814Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01ox-8190000000-4463596c1e2463c117a4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9520000000-ff66beebcf4c1c30a378Spectrum
Biological Properties
Cellular Locations
  • Membrane
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 IDFDB002424
KNApSAcK IDNot Available
Chemspider ID8259588
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10084050
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH 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.. .