2',4,4'-Trihydroxy-6'-methoxy-3',5'-diprenylchalcone (CHEM029014)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 00:51:54 UTC
Update Date2016-11-09 01:18:48 UTC
Accession NumberCHEM029014
Identification
Common Name2',4,4'-Trihydroxy-6'-methoxy-3',5'-diprenylchalcone
ClassSmall Molecule
Description2',4,4'-Trihydroxy-6'-methoxy-3',5'-diprenylchalcone is found in alcoholic beverages. 2',4,4'-Trihydroxy-6'-methoxy-3',5'-diprenylchalcone is a constituent of Humulus lupulus (hops)
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
5'-PrenylxanthohumolChEMBL, HMDB
1-(2-Allyl-4-pentenoyl)-3-cyclohexyl-ureaHMDB
1-(2-Allyl-4-pentenoyl)-3-cyclohexylureaHMDB
3',5'-Diprenyl-4,2',4'-trihydroxy-6-methoxychalconeHMDB
Cyclohexylureide OF diallylacetic acidHMDB
Chemical FormulaC26H30O5
Average Molecular Mass422.513 g/mol
Monoisotopic Mass422.209 g/mol
CAS Registry Number189299-04-5
IUPAC Name(2E)-1-[2,4-dihydroxy-6-methoxy-3,5-bis(3-methylbut-2-en-1-yl)phenyl]-3-(4-hydroxyphenyl)prop-2-en-1-one
Traditional Name5'-prenylxanthohumol
SMILESCOC1=C(CC=C(C)C)C(O)=C(CC=C(C)C)C(O)=C1C(=O)\C=C\C1=CC=C(O)C=C1
InChI IdentifierInChI=1S/C26H30O5/c1-16(2)6-13-20-24(29)21(14-7-17(3)4)26(31-5)23(25(20)30)22(28)15-10-18-8-11-19(27)12-9-18/h6-12,15,27,29-30H,13-14H2,1-5H3/b15-10+
InChI KeyHOTYOZVURUOVTK-XNTDXEJSSA-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
  • Phenoxy compound
  • Phenol ether
  • Resorcinol
  • Styrene
  • Anisole
  • Methoxybenzene
  • Benzoyl
  • Aryl ketone
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Phenol
  • Benzenoid
  • Monocyclic benzene moiety
  • Acryloyl-group
  • Vinylogous acid
  • Enone
  • Alpha,beta-unsaturated ketone
  • 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 Solubility0.0026 g/LALOGPS
logP4.9ALOGPS
logP6.93ChemAxon
logS-5.2ALOGPS
pKa (Strongest Acidic)7.52ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area86.99 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity127.77 m³·mol⁻¹ChemAxon
Polarizability48.57 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-2209500000-f20b7e3fee6f4c45f6feSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-00di-1000149000-bc674c833e12b376e8f5Spectrum
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, Positivesplash10-00di-0117900000-a335ebb379930e5fd4fbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014j-2329200000-b79ee9ad5ffe140953d6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-3491100000-2332d88a95bb72f33f1bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0111900000-428ca0419ec0b196add9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05dj-0594500000-137b30792da0a61e1685Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ab9-1943000000-0ae263245b18cbdd7260Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0010900000-6b487ccdc37bafb1c66cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0118900000-9b9e64079ea916e565efSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014r-0679100000-759479e32c5093ceb005Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00xr-0108900000-47305229004f40c27c76Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kb-0069000000-cafa2774bf7d4825f877Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-0195000000-3096c962fda8b95e0e86Spectrum
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 IDHMDB0035066
FooDB IDFDB013690
Phenol Explorer IDNot Available
KNApSAcK IDC00014473
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID10361526
ChEBI IDNot Available
PubChem Compound ID23250008
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.