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Showing Compound Xanthohumol D (FDB013607)

Record Information
Version1.0
Creation date2010-04-08 22:10:48 UTC
Update date2025-11-19 00:05:24 UTC
Primary IDFDB013607
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameXanthohumol D
DescriptionXanthohumol D 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, xanthohumol D is considered to be a flavonoid. Xanthohumol D has been detected, but not quantified in, alcoholic beverages. This could make xanthohumol D a potential biomarker for the consumption of these foods. Based on a literature review a small amount of articles have been published on Xanthohumol D.
CAS Number274675-25-1
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
3'-(2-Hydroxy-3-methylbutyl-3-enyl)-4,2',4'-trihydroxy-6'-methoxychalconeChEBI
rac-(2E)-1-{2,4-dihydroxy-3-[2-hydroxy-3-methyl-3-but-3-enyl]-6-methoxyphenyl}-3-(4-hydroxyphenyl)-2-propen-1-oneChEBI
Xanthohumol Ddb_source
Predicted Properties
PropertyValueSource
Water Solubility0.046 g/LALOGPS
logP2.85ALOGPS
logP4.03ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)7.97ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area107.22 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity103.97 m³·mol⁻¹ChemAxon
Polarizability39.55 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC21H22O6
IUPAC name(2E)-1-[2,4-dihydroxy-3-(2-hydroxy-3-methylbut-3-en-1-yl)-6-methoxyphenyl]-3-(4-hydroxyphenyl)prop-2-en-1-one
InChI IdentifierInChI=1S/C21H22O6/c1-12(2)17(24)10-15-18(25)11-19(27-3)20(21(15)26)16(23)9-6-13-4-7-14(22)8-5-13/h4-9,11,17,22,24-26H,1,10H2,2-3H3/b9-6+
InChI KeyIIWLGOCXDBSFCM-RMKNXTFCSA-N
Isomeric SMILESCOC1=C(C(=O)\C=C\C2=CC=C(O)C=C2)C(O)=C(CC(O)C(C)=C)C(O)=C1
Average Molecular Weight370.3958
Monoisotopic Molecular Weight370.141638436
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
  • Phenoxy compound
  • Benzoyl
  • Phenol ether
  • Resorcinol
  • Styrene
  • Aryl ketone
  • Methoxybenzene
  • Anisole
  • 1-hydroxy-2-unsubstituted benzenoid
  • 1-hydroxy-4-unsubstituted benzenoid
  • Alkyl aryl ether
  • Phenol
  • Benzenoid
  • Monocyclic benzene moiety
  • Acryloyl-group
  • Alpha,beta-unsaturated ketone
  • Vinylogous acid
  • Enone
  • Secondary alcohol
  • Ketone
  • Ether
  • Organooxygen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Alcohol
  • 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
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 68.10%; H 5.99%; O 25.92%DFC
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV Data[neutral] lmax 369 (log e 4.42) (MeOH)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSXanthohumol D, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0fdp-9257000000-e93616bcdfc00d5f0effSpectrum
Predicted GC-MSXanthohumol D, 4 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0006-4100159000-a73946662fee744891e0Spectrum
Predicted GC-MSXanthohumol D, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fk9-0129000000-f79c99b20767293c10632016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00ds-9343000000-2a20e5aedac4bddb93242016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0l7i-6940000000-25b60ac9ed7eff1613a52016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0039000000-692ffe7dfab4150019f02016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0671-1493000000-424d244d7b00e13bc8862016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-067i-9520000000-677eddaac31484f3246b2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fk9-0019000000-11a1964c498d91ff11322021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f6t-1963000000-6e9da9f0627794e556672021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-2910000000-a64df3dda5e77ae4f8002021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0009000000-53e6b228c1fcbc5c164f2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-1749000000-2a4c83fe1b493b0ee4752021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-2933000000-c39e9b1fa1c7eef6c3d52021-09-25View Spectrum
NMRNot Available
ChemSpider ID8492534
ChEMBL IDCHEMBL479500
KEGG Compound IDNot Available
Pubchem Compound ID10317069
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB35003
CRC / DFC (Dictionary of Food Compounds) IDCMD59-M:JFO56-O
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDC00014472
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
FoodReference
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