Hmdb loader
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 18:26:50 UTC
Update Date2022-03-07 02:53:49 UTC
HMDB IDHMDB0033691
Secondary Accession Numbers
  • HMDB33691
Metabolite Identification
Common Name2'-Hydroxy-4',6'-dimethoxychalcone
Description2'-Hydroxy-4',6'-dimethoxychalcone, also known as 4',6'-dimethoxy-2'-hydroxychalcone, belongs to the class of organic compounds known as 2'-hydroxychalcones. These are organic compounds containing chalcone skeleton that carries a hydroxyl group at the 2'-position. Thus, 2'-hydroxy-4',6'-dimethoxychalcone is considered to be a flavonoid. 2'-Hydroxy-4',6'-dimethoxychalcone has been detected, but not quantified in, beverages. This could make 2'-hydroxy-4',6'-dimethoxychalcone a potential biomarker for the consumption of these foods. 2'-Hydroxy-4',6'-dimethoxychalcone is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on 2'-Hydroxy-4',6'-dimethoxychalcone.
Structure
Data?1563862445
Synonyms
ValueSource
4',6'-Dimethoxy-2'-hydroxychalconeChEBI
CHALCONE,2-hydroxy-4,6-dimethylHMDB
Flavokawain bHMDB
Flavokawin bHMDB
2'-Hydroxy-4',6'-dimethoxychalconeChEBI
Flavokavin bMeSH
Flavokavain bMeSH
Chemical FormulaC17H16O4
Average Molecular Weight284.3065
Monoisotopic Molecular Weight284.104859
IUPAC Name(2E)-1-(2-hydroxy-4,6-dimethoxyphenyl)-3-phenylprop-2-en-1-one
Traditional Nameflavokavain B
CAS Registry Number1775-97-9
SMILES
COC1=CC(O)=C(C(=O)\C=C\C2=CC=CC=C2)C(OC)=C1
InChI Identifier
InChI=1S/C17H16O4/c1-20-13-10-15(19)17(16(11-13)21-2)14(18)9-8-12-6-4-3-5-7-12/h3-11,19H,1-2H3/b9-8+
InChI KeyQKQLSQLKXBHUSO-CMDGGOBGSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 2'-hydroxychalcones. These are organic compounds containing chalcone skeleton that carries a hydroxyl group at the 2'-position.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassLinear 1,3-diarylpropanoids
Sub ClassChalcones and dihydrochalcones
Direct Parent2'-Hydroxychalcones
Alternative Parents
Substituents
  • 2'-hydroxychalcone
  • Cinnamylphenol
  • Methoxyphenol
  • Dimethoxybenzene
  • M-dimethoxybenzene
  • Methoxybenzene
  • Anisole
  • Benzoyl
  • Aryl ketone
  • Phenoxy compound
  • Styrene
  • Phenol ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • 1-hydroxy-4-unsubstituted benzenoid
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Vinylogous acid
  • Alpha,beta-unsaturated ketone
  • Enone
  • Acryloyl-group
  • Ketone
  • Ether
  • Organic oxide
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point91 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.021 g/LALOGPS
logP3.9ALOGPS
logP3.92ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)8.19ChemAxon
pKa (Strongest Basic)-4.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area55.76 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity81.78 m³·mol⁻¹ChemAxon
Polarizability30.54 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
DeepCCS[M+H]+168.68930932474
DeepCCS[M-H]-166.33130932474
DeepCCS[M-2H]-199.21730932474
DeepCCS[M+Na]+174.78230932474
AllCCS[M+H]+167.032859911
AllCCS[M+H-H2O]+163.132859911
AllCCS[M+NH4]+170.532859911
AllCCS[M+Na]+171.532859911
AllCCS[M-H]-168.432859911
AllCCS[M+Na-2H]-168.132859911
AllCCS[M+HCOO]-167.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
2'-Hydroxy-4',6'-dimethoxychalconeCOC1=CC(O)=C(C(=O)\C=C\C2=CC=CC=C2)C(OC)=C13760.4Standard polar33892256
2'-Hydroxy-4',6'-dimethoxychalconeCOC1=CC(O)=C(C(=O)\C=C\C2=CC=CC=C2)C(OC)=C12476.5Standard non polar33892256
2'-Hydroxy-4',6'-dimethoxychalconeCOC1=CC(O)=C(C(=O)\C=C\C2=CC=CC=C2)C(OC)=C12653.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
2'-Hydroxy-4',6'-dimethoxychalcone,1TMS,isomer #1COC1=CC(OC)=C(C(=O)/C=C/C2=CC=CC=C2)C(O[Si](C)(C)C)=C12517.6Semi standard non polar33892256
2'-Hydroxy-4',6'-dimethoxychalcone,1TBDMS,isomer #1COC1=CC(OC)=C(C(=O)/C=C/C2=CC=CC=C2)C(O[Si](C)(C)C(C)(C)C)=C12784.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 2'-Hydroxy-4',6'-dimethoxychalcone GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-2790000000-55c54509736fc2799cd62017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2'-Hydroxy-4',6'-dimethoxychalcone GC-MS (1 TMS) - 70eV, Positivesplash10-006x-6449000000-886bb5f544d421c5c1c52017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2'-Hydroxy-4',6'-dimethoxychalcone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2'-Hydroxy-4',6'-dimethoxychalcone 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 - 2'-Hydroxy-4',6'-dimethoxychalcone LC-ESI-qTof , Positive-QTOFsplash10-00lr-0900000000-887bb7e62bbec731a8f72017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2'-Hydroxy-4',6'-dimethoxychalcone , positive-QTOFsplash10-001i-0900000000-f456ae52791e208e7a0e2017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2'-Hydroxy-4',6'-dimethoxychalcone 10V, Negative-QTOFsplash10-001i-0390000000-d17368362a50f37792992016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2'-Hydroxy-4',6'-dimethoxychalcone 20V, Negative-QTOFsplash10-0ue9-1960000000-077f2945d8d4fb6633302016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2'-Hydroxy-4',6'-dimethoxychalcone 40V, Negative-QTOFsplash10-0kvt-4930000000-f1b41017e8bbdc9e57302016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2'-Hydroxy-4',6'-dimethoxychalcone 10V, Negative-QTOFsplash10-001i-0290000000-49df8bccba954e251b612021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2'-Hydroxy-4',6'-dimethoxychalcone 20V, Negative-QTOFsplash10-00lr-0690000000-151e1951cbdb6b0cb17d2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2'-Hydroxy-4',6'-dimethoxychalcone 40V, Negative-QTOFsplash10-0f9f-7940000000-0032eeb54416d6c7298e2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2'-Hydroxy-4',6'-dimethoxychalcone 10V, Positive-QTOFsplash10-000i-0190000000-d2b945cda2c651f982042016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2'-Hydroxy-4',6'-dimethoxychalcone 20V, Positive-QTOFsplash10-001r-0890000000-3c934b149da6c66eacc52016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2'-Hydroxy-4',6'-dimethoxychalcone 40V, Positive-QTOFsplash10-0udi-1920000000-34edd66b5dda77a0b65e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2'-Hydroxy-4',6'-dimethoxychalcone 10V, Positive-QTOFsplash10-000i-0390000000-bd10f8d7e501a32ab8cd2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2'-Hydroxy-4',6'-dimethoxychalcone 20V, Positive-QTOFsplash10-001i-0900000000-05e1177b781e4c2c11292021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2'-Hydroxy-4',6'-dimethoxychalcone 40V, Positive-QTOFsplash10-0udi-2900000000-9657eea0d14d444ffe8a2021-09-22Wishart 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 IDFDB011797
KNApSAcK IDC00006936
Chemspider ID4511912
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5356121
PDB IDNot Available
ChEBI ID65899
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.. .