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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 19:04:29 UTC
Update Date2022-03-07 02:54:02 UTC
HMDB IDHMDB0034270
Secondary Accession Numbers
  • HMDB34270
Metabolite Identification
Common Name5,6-Dihydro-5-hydroxy-6-methyl-2H-pyran-2-one
Description5,6-Dihydro-5-hydroxy-6-methyl-2H-pyran-2-one 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-5-hydroxy-6-methyl-2H-pyran-2-one has been detected, but not quantified in, beverages. This could make 5,6-dihydro-5-hydroxy-6-methyl-2H-pyran-2-one a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 5,6-Dihydro-5-hydroxy-6-methyl-2H-pyran-2-one.
Structure
Data?1588284668
Synonyms
ValueSource
56-DehydrokawainChEMBL, HMDB
56-DehydrokawinChEMBL, HMDB
(e)-4-Methoxy-6-(2-phenylethenyl)-2H-pyran-2-oneHMDB
2H-Pyran-2-one, 4-methoxy-6-(2-phenylethenyl)-, (e)- (9ci)HMDB
4-Methoxy-6-(2-phenylethenyl)-(e)-2H-pyran-2-oneHMDB
4-Methoxy-6-(2-phenylethenyl)-2H-pyran-2-oneHMDB
4-Methoxy-6-styryl-(e)-2H-pyran-2-oneHMDB
4-Methoxy-6-styryl-2H-pyran-2-oneHMDB
4-Methoxy-6-[(e)-2-phenylethenyl]-2H-pyran-2-oneHMDB
4-Methoxy-6-[(e)-2-phenylvinyl]-2H-pyran-2-oneHMDB
5,6-DehydrokawainHMDB
DemethoxyyangoninHMDB
DesmethoxyyangoninHMDB
DMYHMDB
5,6-Dehydrokawain, (e)-isomerMeSH, HMDB
Chemical FormulaC14H12O3
Average Molecular Weight228.2433
Monoisotopic Molecular Weight228.07864425
IUPAC Name4-methoxy-6-[(E)-2-phenylethenyl]-2H-pyran-2-one
Traditional Namedesmethoxyyangonin
CAS Registry Number15345-89-8
SMILES
COC1=CC(=O)OC(\C=C\C2=CC=CC=C2)=C1
InChI Identifier
InChI=1S/C14H12O3/c1-16-13-9-12(17-14(15)10-13)8-7-11-5-3-2-4-6-11/h2-10H,1H3/b8-7+
InChI KeyDKKJNZYHGRUXBS-BQYQJAHWSA-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
  • Styrene
  • Alkyl aryl ether
  • Pyranone
  • Benzenoid
  • Pyran
  • Monocyclic benzene moiety
  • Heteroaromatic compound
  • Vinylogous ester
  • Lactone
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxygen compound
  • Organic oxide
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point138 - 140 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.04 g/LALOGPS
logP3.2ALOGPS
logP2.64ChemAxon
logS-3.8ALOGPS
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area35.53 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity68.74 m³·mol⁻¹ChemAxon
Polarizability24.42 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+156.08931661259
DarkChem[M-H]-156.51631661259
DeepCCS[M+H]+156.02930932474
DeepCCS[M-H]-153.64630932474
DeepCCS[M-2H]-186.57530932474
DeepCCS[M+Na]+162.09730932474
AllCCS[M+H]+149.932859911
AllCCS[M+H-H2O]+145.532859911
AllCCS[M+NH4]+154.032859911
AllCCS[M+Na]+155.132859911
AllCCS[M-H]-151.232859911
AllCCS[M+Na-2H]-150.932859911
AllCCS[M+HCOO]-150.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
5,6-Dihydro-5-hydroxy-6-methyl-2H-pyran-2-oneCOC1=CC(=O)OC(\C=C\C2=CC=CC=C2)=C13324.9Standard polar33892256
5,6-Dihydro-5-hydroxy-6-methyl-2H-pyran-2-oneCOC1=CC(=O)OC(\C=C\C2=CC=CC=C2)=C12141.8Standard non polar33892256
5,6-Dihydro-5-hydroxy-6-methyl-2H-pyran-2-oneCOC1=CC(=O)OC(\C=C\C2=CC=CC=C2)=C12370.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 5,6-Dihydro-5-hydroxy-6-methyl-2H-pyran-2-one GC-MS (Non-derivatized) - 70eV, Positivesplash10-01tc-4970000000-5313253d81990e8f899d2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5,6-Dihydro-5-hydroxy-6-methyl-2H-pyran-2-one GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - 5,6-Dihydro-5-hydroxy-6-methyl-2H-pyran-2-one , positive-QTOFsplash10-0ufu-0930000000-c45b0f14494494198c6c2017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,6-Dihydro-5-hydroxy-6-methyl-2H-pyran-2-one 10V, Positive-QTOFsplash10-004i-0190000000-69ef56e66ed3e2d76e852016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,6-Dihydro-5-hydroxy-6-methyl-2H-pyran-2-one 20V, Positive-QTOFsplash10-004i-1790000000-646967bbc7e9bc2ac6fd2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,6-Dihydro-5-hydroxy-6-methyl-2H-pyran-2-one 40V, Positive-QTOFsplash10-0fb9-3910000000-b624986462c7f4bc3a122016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,6-Dihydro-5-hydroxy-6-methyl-2H-pyran-2-one 10V, Negative-QTOFsplash10-004i-0490000000-c2f830d977ce499b03bc2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,6-Dihydro-5-hydroxy-6-methyl-2H-pyran-2-one 20V, Negative-QTOFsplash10-002f-9340000000-ee86bc62eed6a5fd45772016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,6-Dihydro-5-hydroxy-6-methyl-2H-pyran-2-one 40V, Negative-QTOFsplash10-002f-8900000000-92e15b6d1ede62fa65712016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,6-Dihydro-5-hydroxy-6-methyl-2H-pyran-2-one 10V, Negative-QTOFsplash10-004i-0090000000-f0e0fc28215258fdeb312021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,6-Dihydro-5-hydroxy-6-methyl-2H-pyran-2-one 20V, Negative-QTOFsplash10-004i-0690000000-317865019d785558fd792021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,6-Dihydro-5-hydroxy-6-methyl-2H-pyran-2-one 40V, Negative-QTOFsplash10-004i-9100000000-818ce39c4616027934e52021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,6-Dihydro-5-hydroxy-6-methyl-2H-pyran-2-one 10V, Positive-QTOFsplash10-004i-0290000000-c05a8d84225eb8226a2f2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,6-Dihydro-5-hydroxy-6-methyl-2H-pyran-2-one 20V, Positive-QTOFsplash10-004i-3970000000-057a25d403e514d8d1202021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,6-Dihydro-5-hydroxy-6-methyl-2H-pyran-2-one 40V, Positive-QTOFsplash10-004i-6900000000-8178f04b27a5dbcbba652021-09-25Wishart 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 IDFDB012602
KNApSAcK IDC00002987
Chemspider ID4438012
KEGG Compound IDC09925
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5273621
PDB IDNot Available
ChEBI IDNot Available
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.. .