2'-Hydroxy-4',6'-dimethoxychalcone (CHEM027860)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 00:01:48 UTC
Update Date2016-11-09 01:18:32 UTC
Accession NumberCHEM027860
Identification
Common Name2'-Hydroxy-4',6'-dimethoxychalcone
ClassSmall Molecule
DescriptionA member of the class of chalcones that consists of trans-chalcone substituted by hydroxy group at positions 2' and methoxy groups at positions 4' and 6'. Isolated from Piper methysticum and Piper rusbyi, it exhibits antileishmanial, anti-inflammatory and antineoplastic activities.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
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 Mass284.307 g/mol
Monoisotopic Mass284.105 g/mol
CAS Registry Number1175-97-9
IUPAC Name(2E)-1-(2-hydroxy-4,6-dimethoxyphenyl)-3-phenylprop-2-en-1-one
Traditional Nameflavokavain B
SMILESCOC1=CC(O)=C(C(=O)\C=C\C2=CC=CC=C2)C(OC)=C1
InChI IdentifierInChI=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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted 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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-2790000000-55c54509736fc2799cd6Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-006x-6449000000-886bb5f544d421c5c1c5Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-00lr-0900000000-887bb7e62bbec731a8f7Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-001i-0900000000-f456ae52791e208e7a0eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0190000000-d2b945cda2c651f98204Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001r-0890000000-3c934b149da6c66eacc5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-1920000000-34edd66b5dda77a0b65eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0390000000-d17368362a50f3779299Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ue9-1960000000-077f2945d8d4fb663330Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0kvt-4930000000-f1b41017e8bbdc9e5730Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0290000000-49df8bccba954e251b61Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00lr-0690000000-151e1951cbdb6b0cb17dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0f9f-7940000000-0032eeb54416d6c7298eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0390000000-bd10f8d7e501a32ab8cdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0900000000-05e1177b781e4c2c1129Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-2900000000-9657eea0d14d444ffe8aSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0033691
FooDB IDFDB011797
Phenol Explorer IDNot Available
KNApSAcK IDC00006936
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID4511912
ChEBI ID65899
PubChem Compound ID5356121
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=11830162
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=17354169
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=19537711
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=20112340
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=21543203
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=22540374
7. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.