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Showing Compound Xanthogalenol (FDB013606)

Record Information
Version1.0
Creation date2010-04-08 22:10:48 UTC
Update date2019-11-26 03:08:42 UTC
Primary IDFDB013606
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameXanthogalenol
DescriptionXanthogalenol 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, xanthogalenol is considered to be a flavonoid. Xanthogalenol has been detected, but not quantified in, alcoholic beverages. This could make xanthogalenol a potential biomarker for the consumption of these foods. Based on a literature review a small amount of articles have been published on Xanthogalenol.
CAS Number265659-35-6
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility0.0058 g/LALOGPS
logP3.93ALOGPS
logP5.85ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)7.82ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area86.99 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity103.53 m³·mol⁻¹ChemAxon
Polarizability38.85 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC21H22O5
IUPAC name(2E)-1-[2,6-dihydroxy-4-methoxy-3-(3-methylbut-2-en-1-yl)phenyl]-3-(4-hydroxyphenyl)prop-2-en-1-one
InChI IdentifierInChI=1S/C21H22O5/c1-13(2)4-10-16-19(26-3)12-18(24)20(21(16)25)17(23)11-7-14-5-8-15(22)9-6-14/h4-9,11-12,22,24-25H,10H2,1-3H3/b11-7+
InChI KeyALGFNVZQNNGHPA-YRNVUSSQSA-N
Isomeric SMILESCOC1=C(CC=C(C)C)C(O)=C(C(=O)\C=C\C2=CC=C(O)C=C2)C(O)=C1
Average Molecular Weight354.3964
Monoisotopic Molecular Weight354.146723814
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
  • Phenol ether
  • Resorcinol
  • Styrene
  • Aryl ketone
  • Anisole
  • Methoxybenzene
  • Benzoyl
  • Phenol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • 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
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-MSXanthogalenol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-000j-3459000000-8086a86ef04627fc559aSpectrum
Predicted GC-MSXanthogalenol, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0a4i-1001290000-27ebccdf6673fc73908eSpectrum
Predicted GC-MSXanthogalenol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0129000000-836af65cb4ae74175c882016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05mt-3696000000-ae1e87c202e1b83d37172016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-016r-4910000000-093de7a4a5c7916eede62016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0129000000-a92805839c571d453a6e2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pbd-0955000000-c208ad3f8d4edb90545f2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0avm-1930000000-a40d21950ef93ac5ba5b2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0009000000-cf0d5b7646fbfcac4d812021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0259000000-d59a2bac22530a37d7a62021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014l-1920000000-b28a071e0b0ec5ee32472021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4j-0429000000-a2c14b4be6145244b0682021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0931000000-9a041dc31a2b43b191af2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00or-2911000000-a04ec936ed7cafb4f3cc2021-09-22View Spectrum
NMRNot Available
ChemSpider ID24692988
ChEMBL IDCHEMBL466334
KEGG Compound IDNot Available
Pubchem Compound ID14309735
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB35002
CRC / DFC (Dictionary of Food Compounds) IDCMD59-M:JFO55-N
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDC00014475
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