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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-12 00:09:39 UTC
Update Date2019-07-23 06:27:43 UTC
HMDB IDHMDB0038815
Secondary Accession Numbers
  • HMDB38815
Metabolite Identification
Common Name2',4-Dihydroxy-4',6'-dimethoxy-3'-prenylchalcone
Description2',4-Dihydroxy-4',6'-dimethoxy-3'-prenylchalcone, also known as 4'-methylxanthohumol or 3'-(isoprenyl)-2',4-dihydroxy-4',6'-dimethoxychalcone, 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 lipid molecule. 2',4-Dihydroxy-4',6'-dimethoxy-3'-prenylchalcone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, 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.
Structure
Data?1563863263
Synonyms
ValueSource
3'-(Isoprenyl)-2',4-dihydroxy-4',6'-dimethoxychalconeChEBI
4'-MethylxanthohumolChEBI
4'-O-MethylxanthohumolHMDB
Chemical FormulaC22H24O5
Average Molecular Weight368.423
Monoisotopic Molecular Weight368.162373878
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
CAS Registry Number123316-63-2
SMILES
COC1=CC(OC)=C(C(=O)\C=C\C2=CC=C(O)C=C2)C(O)=C1CC=C(C)C
InChI Identifier
InChI=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
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Role

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point152 - 153 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot 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
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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 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
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 IDFDB018241
KNApSAcK IDC00007100
Chemspider ID9134771
KEGG Compound IDNot Available
BioCyc IDCPD-7122
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10959555
PDB IDNot Available
ChEBI ID136828
Food Biomarker OntologyNot Available
VMH 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.. .