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Showing Compound 2',4-Dihydroxy-4',6'-dimethoxy-3'-prenylchalcone (FDB018241)

Record Information
Version1.0
Creation date2010-04-08 22:13:35 UTC
Update date2019-11-26 03:15:54 UTC
Primary IDFDB018241
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name2',4-Dihydroxy-4',6'-dimethoxy-3'-prenylchalcone
Description2',4-Dihydroxy-4',6'-dimethoxy-3'-prenylchalcone, also known as 3'-(isoprenyl)-2',4-dihydroxy-4',6'-dimethoxychalcone or 4'-methylxanthohumol, belongs to the class of organic compounds known as 3-prenylated chalcones. These are chalcones featuring a C5-isoprenoid unit at the 3-position. Thus, 2',4-dihydroxy-4',6'-dimethoxy-3'-prenylchalcone is considered to be a flavonoid. 2',4-Dihydroxy-4',6'-dimethoxy-3'-prenylchalcone has been detected, but not quantified in, alcoholic beverages. This could make 2',4-dihydroxy-4',6'-dimethoxy-3'-prenylchalcone a potential biomarker for the consumption of these foods. Based on a literature review a small amount of articles have been published on 2',4-Dihydroxy-4',6'-dimethoxy-3'-prenylchalcone.
CAS Number123316-63-2
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
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
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC22H24O5
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
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
Isomeric SMILESCOC1=CC(OC)=C(C(=O)\C=C\C2=CC=C(O)C=C2)C(O)=C1CC=C(C)C
Average Molecular Weight368.423
Monoisotopic Molecular Weight368.162373878
Classification
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
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Role

Biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS2',4-Dihydroxy-4',6'-dimethoxy-3'-prenylchalcone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0uy4-2229000000-91d0f692699ee98853d7Spectrum
Predicted GC-MS2',4-Dihydroxy-4',6'-dimethoxy-3'-prenylchalcone, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0002-1001900000-7915e9297ce4b84689cdSpectrum
Predicted GC-MS2',4-Dihydroxy-4',6'-dimethoxy-3'-prenylchalcone, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS2',4-Dihydroxy-4',6'-dimethoxy-3'-prenylchalcone, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0129000000-d9c210cd27ac58a81b552016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014j-3579000000-072a93c3716d402964f82016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-066r-4950000000-278d3207d60602ceb4472016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0129000000-951fd88ef1d77bb733892016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-06di-0898000000-fcbcdac9cc4a0b46b9e02016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-1942000000-928b09421cdf531813612016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0009000000-a11611863089d648721c2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014j-0349000000-06a9f5a69250de70d96d2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-1923000000-37433065aaf1a43748ff2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-02t9-0009000000-b66045a717a3b178254b2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00ke-0920000000-dfc6ccfe471053e9c0502021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05mp-1931000000-720938b281826b22e0052021-09-22View Spectrum
NMRNot Available
ChemSpider ID9134771
ChEMBL IDCHEMBL466335
KEGG Compound IDNot Available
Pubchem Compound ID10959555
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB38815
CRC / DFC (Dictionary of Food Compounds) IDCMD59-M:LHS46-P
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDC00007100
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
Processing...
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference