Hmdb loader
Survey
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
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:53:15 UTC
Update Date2022-03-07 02:53:33 UTC
HMDB IDHMDB0033015
Secondary Accession Numbers
  • HMDB33015
Metabolite Identification
Common Name5,6-Dihydroyangonin
Description5,6-Dihydroyangonin 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-Dihydroyangonin has been detected, but not quantified in, beverages. This could make 5,6-dihydroyangonin a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 5,6-Dihydroyangonin.
Structure
Data?1563862339
SynonymsNot Available
Chemical FormulaC15H16O4
Average Molecular Weight260.2851
Monoisotopic Molecular Weight260.104859
IUPAC Name4-methoxy-6-[(E)-2-(4-methoxyphenyl)ethenyl]-5,6-dihydro-2H-pyran-2-one
Traditional Name4-methoxy-6-[(E)-2-(4-methoxyphenyl)ethenyl]-5,6-dihydropyran-2-one
CAS Registry Number3328-60-7
SMILES
COC1=CC(=O)OC(C1)\C=C\C1=CC=C(OC)C=C1
InChI Identifier
InChI=1S/C15H16O4/c1-17-12-6-3-11(4-7-12)5-8-13-9-14(18-2)10-15(16)19-13/h3-8,10,13H,9H2,1-2H3/b8-5+
InChI KeyAYXCIWVJOBQVFH-VMPITWQZSA-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
  • Styrene
  • Alkyl aryl ether
  • Dihydropyranone
  • Monocyclic benzene moiety
  • Benzenoid
  • Pyran
  • Vinylogous ester
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Lactone
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Organoheterocyclic compound
  • Ether
  • Oxacycle
  • Carboxylic acid derivative
  • Organooxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organic oxide
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.024 g/LALOGPS
logP2.8ALOGPS
logP2.28ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)16.54ChemAxon
pKa (Strongest Basic)-4.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area44.76 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity73.82 m³·mol⁻¹ChemAxon
Polarizability27.99 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+166.99131661259
DarkChem[M-H]-165.53931661259
DeepCCS[M+H]+162.73130932474
DeepCCS[M-H]-160.36230932474
DeepCCS[M-2H]-193.24830932474
DeepCCS[M+Na]+168.81330932474
AllCCS[M+H]+162.032859911
AllCCS[M+H-H2O]+158.032859911
AllCCS[M+NH4]+165.632859911
AllCCS[M+Na]+166.732859911
AllCCS[M-H]-164.032859911
AllCCS[M+Na-2H]-164.032859911
AllCCS[M+HCOO]-164.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
5,6-DihydroyangoninCOC1=CC(=O)OC(C1)\C=C\C1=CC=C(OC)C=C13440.7Standard polar33892256
5,6-DihydroyangoninCOC1=CC(=O)OC(C1)\C=C\C1=CC=C(OC)C=C12296.2Standard non polar33892256
5,6-DihydroyangoninCOC1=CC(=O)OC(C1)\C=C\C1=CC=C(OC)C=C12543.8Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 5,6-Dihydroyangonin GC-MS (Non-derivatized) - 70eV, Positivesplash10-0avj-7690000000-4f31aed096680f17f0f92017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5,6-Dihydroyangonin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,6-Dihydroyangonin 10V, Positive-QTOFsplash10-03di-0290000000-e9b6faf18e44f7a7ba192016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,6-Dihydroyangonin 20V, Positive-QTOFsplash10-0bt9-2950000000-992a744a02842e1443db2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,6-Dihydroyangonin 40V, Positive-QTOFsplash10-0pb9-3900000000-62061a7d6632180af60c2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,6-Dihydroyangonin 10V, Negative-QTOFsplash10-0a4i-0190000000-dce7120862c5af83c1452016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,6-Dihydroyangonin 20V, Negative-QTOFsplash10-052f-8290000000-c7feee5b7fd13c95eac72016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,6-Dihydroyangonin 40V, Negative-QTOFsplash10-052f-9710000000-a8180c57fc4e720e1bfa2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,6-Dihydroyangonin 10V, Negative-QTOFsplash10-0a4i-0090000000-3cd3c62664dcb4e206a62021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,6-Dihydroyangonin 20V, Negative-QTOFsplash10-05o0-2950000000-dc14ca5ba3dc0cbd7fd22021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,6-Dihydroyangonin 40V, Negative-QTOFsplash10-014i-2900000000-b4e43abe1873fe0b9d4c2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,6-Dihydroyangonin 10V, Positive-QTOFsplash10-03di-0090000000-a50a62b73165b69634542021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,6-Dihydroyangonin 20V, Positive-QTOFsplash10-0002-1920000000-509469f7e6cba3967a392021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,6-Dihydroyangonin 40V, Positive-QTOFsplash10-004l-8900000000-266c6fd207f31b7513d42021-09-22Wishart LabView Spectrum
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
FooDB IDFDB011007
KNApSAcK IDNot Available
Chemspider ID9797803
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound11623055
PDB IDNot Available
ChEBI ID174416
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents 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.. .