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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:37:33 UTC
Update Date2022-03-07 02:52:35 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. Based on a literature review very few articles have been published on 5,6-Dihydro-4-methoxy-6-[2-(4-methoxyphenyl)ethyl]-2H-pyran-2-one.
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
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point89 - 90 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility429.4 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+164.44831661259
DarkChem[M-H]-165.81531661259
DeepCCS[M+H]+159.87130932474
DeepCCS[M-H]-157.51330932474
DeepCCS[M-2H]-190.60130932474
DeepCCS[M+Na]+165.96430932474
AllCCS[M+H]+163.332859911
AllCCS[M+H-H2O]+159.432859911
AllCCS[M+NH4]+166.932859911
AllCCS[M+Na]+167.932859911
AllCCS[M-H]-166.132859911
AllCCS[M+Na-2H]-166.332859911
AllCCS[M+HCOO]-166.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
5,6-Dihydro-4-methoxy-6-[2-(4-methoxyphenyl)ethyl]-2H-pyran-2-oneCOC1=CC(=O)OC(CCC2=CC=C(OC)C=C2)C13280.3Standard polar33892256
5,6-Dihydro-4-methoxy-6-[2-(4-methoxyphenyl)ethyl]-2H-pyran-2-oneCOC1=CC(=O)OC(CCC2=CC=C(OC)C=C2)C12196.4Standard non polar33892256
5,6-Dihydro-4-methoxy-6-[2-(4-methoxyphenyl)ethyl]-2H-pyran-2-oneCOC1=CC(=O)OC(CCC2=CC=C(OC)C=C2)C12416.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 5,6-Dihydro-4-methoxy-6-[2-(4-methoxyphenyl)ethyl]-2H-pyran-2-one GC-MS (Non-derivatized) - 70eV, Positivesplash10-05fr-5950000000-8a3df98cf6c112a79d662017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5,6-Dihydro-4-methoxy-6-[2-(4-methoxyphenyl)ethyl]-2H-pyran-2-one GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5,6-Dihydro-4-methoxy-6-[2-(4-methoxyphenyl)ethyl]-2H-pyran-2-one 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-Dihydro-4-methoxy-6-[2-(4-methoxyphenyl)ethyl]-2H-pyran-2-one 10V, Positive-QTOFsplash10-03di-0290000000-d73f7cd4a104071191832016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,6-Dihydro-4-methoxy-6-[2-(4-methoxyphenyl)ethyl]-2H-pyran-2-one 20V, Positive-QTOFsplash10-01ot-1930000000-8271e8b3696d4038830a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,6-Dihydro-4-methoxy-6-[2-(4-methoxyphenyl)ethyl]-2H-pyran-2-one 40V, Positive-QTOFsplash10-0pb9-4900000000-f1677005f630a2241c002016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,6-Dihydro-4-methoxy-6-[2-(4-methoxyphenyl)ethyl]-2H-pyran-2-one 10V, Negative-QTOFsplash10-03di-0090000000-a5b52057c6bf7fb418142016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,6-Dihydro-4-methoxy-6-[2-(4-methoxyphenyl)ethyl]-2H-pyran-2-one 20V, Negative-QTOFsplash10-01ox-8190000000-4463596c1e2463c117a42016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,6-Dihydro-4-methoxy-6-[2-(4-methoxyphenyl)ethyl]-2H-pyran-2-one 40V, Negative-QTOFsplash10-052f-9520000000-ff66beebcf4c1c30a3782016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,6-Dihydro-4-methoxy-6-[2-(4-methoxyphenyl)ethyl]-2H-pyran-2-one 10V, Positive-QTOFsplash10-01ot-0790000000-b1183b2d45a69d3cee0d2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,6-Dihydro-4-methoxy-6-[2-(4-methoxyphenyl)ethyl]-2H-pyran-2-one 20V, Positive-QTOFsplash10-0002-1910000000-8a51733990160e1326ff2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,6-Dihydro-4-methoxy-6-[2-(4-methoxyphenyl)ethyl]-2H-pyran-2-one 40V, Positive-QTOFsplash10-004l-9710000000-19546c1334387a67f1232021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,6-Dihydro-4-methoxy-6-[2-(4-methoxyphenyl)ethyl]-2H-pyran-2-one 10V, Negative-QTOFsplash10-000i-0900000000-d5fce93334c873464e4a2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,6-Dihydro-4-methoxy-6-[2-(4-methoxyphenyl)ethyl]-2H-pyran-2-one 20V, Negative-QTOFsplash10-000i-0900000000-7423acc6bb5078b1aef72021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,6-Dihydro-4-methoxy-6-[2-(4-methoxyphenyl)ethyl]-2H-pyran-2-one 40V, Negative-QTOFsplash10-014i-3900000000-678ef6594e8c4cad141d2021-09-23Wishart 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 IDFDB002424
KNApSAcK IDC00058121
Chemspider ID8259588
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10084050
PDB IDNot Available
ChEBI ID157716
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1820931
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.. .