Record Information
Version1.0
Creation date2010-04-08 22:10:45 UTC
Update date2019-11-26 03:08:30 UTC
Primary IDFDB013502
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameXanthohumol E
DescriptionXanthohumol E 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 e is considered to be a flavonoid. Xanthohumol E has been detected, but not quantified in, alcoholic beverages. This could make xanthohumol e a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Xanthohumol E.
CAS NumberNot Available
Structure
Thumb
Synonyms
SynonymSource
Predicted Properties
PropertyValueSource
Water Solubility0.0076 g/LALOGPS
logP4.51ALOGPS
logP6.26ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)7.64ChemAxon
pKa (Strongest Basic)-5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area86.99 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity121.46 m³·mol⁻¹ChemAxon
Polarizability45.52 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC25H26O5
IUPAC name(2E)-1-[5,7-dihydroxy-2,2-dimethyl-6-(3-methylbut-2-en-1-yl)-2H-chromen-8-yl]-3-(4-hydroxyphenyl)prop-2-en-1-one
InChI IdentifierInChI=1S/C25H26O5/c1-15(2)5-11-18-22(28)19-13-14-25(3,4)30-24(19)21(23(18)29)20(27)12-8-16-6-9-17(26)10-7-16/h5-10,12-14,26,28-29H,11H2,1-4H3/b12-8+
InChI KeyKRZGSPKDWYNTHE-XYOKQWHBSA-N
Isomeric SMILESCC(C)=CCC1=C(O)C2=C(OC(C)(C)C=C2)C(C(=O)\C=C\C2=CC=C(O)C=C2)=C1O
Average Molecular Weight406.4709
Monoisotopic Molecular Weight406.178023942
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
  • Hydroxycinnamic acid or derivatives
  • 2,2-dimethyl-1-benzopyran
  • Benzopyran
  • 1-benzopyran
  • Styrene
  • Aryl ketone
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Acryloyl-group
  • Enone
  • Vinylogous acid
  • Alpha,beta-unsaturated ketone
  • Ketone
  • Oxacycle
  • Ether
  • Organoheterocyclic compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Role

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 73.87%; H 6.45%; O 19.68%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 () (MeOH)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSXanthohumol E, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0006-3419000000-6b57ba67f36b750282ffSpectrum
Predicted GC-MSXanthohumol E, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0a4i-2100039000-e2df2595710013827aedSpectrum
Predicted GC-MSXanthohumol E, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-1228900000-be84c08d3627bfb84386Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05mt-3449100000-1308efc4968142069b76Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-066r-7693000000-f36e5b6f6382d4fc2afbSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0131900000-510a93d327c759852a6dSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0692300000-e75638ba22e4a154b3ccSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00bd-0952000000-b5d65dccff1b1660516fSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0009300000-8744eba2a46dd5076742Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0094200000-e4eac9c491fed44bc73dSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00ls-0189000000-3dce236f23c346862e80Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0000900000-7b5974fd53d3ffdb29adSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0163900000-1b15da60ece2daff6787Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-5973000000-d1f27b7331f17adc1166Spectrum
NMRNot Available
ChemSpider ID24845983
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID25245324
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB34917
CRC / DFC (Dictionary of Food Compounds) IDJDS30-I:JDS30-I
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDC00014474
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