2',4-Dihydroxy-4',6'-dimethoxy-3'-prenylchalcone (CHEM032158)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 03:10:56 UTC
Update Date2016-11-09 01:19:24 UTC
Accession NumberCHEM032158
Identification
Common Name2',4-Dihydroxy-4',6'-dimethoxy-3'-prenylchalcone
ClassSmall Molecule
DescriptionA member of the class of chalcones that is trans-chalcone substituted by hydroxy groups at positions 2' and 4, methoxy group at positions 4' and 6' and a prenyl group at position 3'.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
3'-(Isoprenyl)-2',4-dihydroxy-4',6'-dimethoxychalconeChEBI
4'-MethylxanthohumolChEBI
4'-O-MethylxanthohumolHMDB
Chemical FormulaC22H24O5
Average Molecular Mass368.423 g/mol
Monoisotopic Mass368.162 g/mol
CAS Registry Number123316-63-2
IUPAC Name(2E)-1-[2-hydroxy-4,6-dimethoxy-3-(3-methylbut-2-en-1-yl)phenyl]-3-(4-hydroxyphenyl)prop-2-en-1-one
Traditional Name4'-O-methylxanthohumol
SMILESCOC1=CC(OC)=C(C(=O)\C=C\C2=CC=C(O)C=C2)C(O)=C1CC=C(C)C
InChI IdentifierInChI=1S/C22H24O5/c1-14(2)5-11-17-19(26-3)13-20(27-4)21(22(17)25)18(24)12-8-15-6-9-16(23)10-7-15/h5-10,12-13,23,25H,11H2,1-4H3/b12-8+
InChI KeyUVBDKJHYMQEAQV-XYOKQWHBSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as 3-prenylated chalcones. These are chalcones featuring a C5-isoprenoid unit at the 3-position.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassLinear 1,3-diarylpropanoids
Sub ClassChalcones and dihydrochalcones
Direct Parent3-prenylated chalcones
Alternative Parents
Substituents
  • 3-prenylated chalcone
  • 2'-hydroxychalcone
  • Cinnamylphenol
  • Hydroxycinnamic acid or derivatives
  • Methoxyphenol
  • Dimethoxybenzene
  • M-dimethoxybenzene
  • Anisole
  • Methoxybenzene
  • Benzoyl
  • Aryl ketone
  • Phenoxy compound
  • Phenol ether
  • Styrene
  • Alkyl aryl ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • 1-hydroxy-4-unsubstituted benzenoid
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Acryloyl-group
  • Enone
  • Alpha,beta-unsaturated ketone
  • Vinylogous acid
  • Ketone
  • Ether
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Organic oxygen 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 Solubility0.0033 g/LALOGPS
logP3.84ALOGPS
logP5.35ChemAxon
logS-5ALOGPS
pKa (Strongest Acidic)7.97ChemAxon
pKa (Strongest Basic)-4.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area75.99 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity108.01 m³·mol⁻¹ChemAxon
Polarizability40.95 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0uy4-2229000000-91d0f692699ee98853d7Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0002-1001900000-7915e9297ce4b84689cdSpectrum
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
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0129000000-d9c210cd27ac58a81b55Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014j-3579000000-072a93c3716d402964f8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-066r-4950000000-278d3207d60602ceb447Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0129000000-951fd88ef1d77bb73389Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-06di-0898000000-fcbcdac9cc4a0b46b9e0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-1942000000-928b09421cdf53181361Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0009000000-a11611863089d648721cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014j-0349000000-06a9f5a69250de70d96dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-1923000000-37433065aaf1a43748ffSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-02t9-0009000000-b66045a717a3b178254bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00ke-0920000000-dfc6ccfe471053e9c050Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05mp-1931000000-720938b281826b22e005Spectrum
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 IDHMDB0038815
FooDB IDFDB018241
Phenol Explorer IDNot Available
KNApSAcK IDC00007100
BiGG IDNot Available
BioCyc IDCPD-7122
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID9134771
ChEBI ID136828
PubChem Compound ID10959555
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=10783982
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=26162028
3. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.