Xanthohumol C (CHEM024256)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 21:35:29 UTC
Update Date2016-11-09 01:17:51 UTC
Accession NumberCHEM024256
Identification
Common NameXanthohumol C
ClassSmall Molecule
DescriptionXanthohumol C is found in alcoholic beverages. Xanthohumol C is a constituent of the female inflorescence of hops (Humulus lupulus)
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
DehydrocycloxanthohumolHMDB
5''-Hydroxy-6'',6''-dimethyldihydropyrano(2'',3''-b)-4,4'-dihydroxy-6'-methoxychalconeHMDB
Chemical FormulaC21H20O5
Average Molecular Mass352.381 g/mol
Monoisotopic Mass352.131 g/mol
CAS Registry Number189299-05-6
IUPAC Name(2E)-1-(5-hydroxy-7-methoxy-2,2-dimethyl-2H-chromen-6-yl)-3-(4-hydroxyphenyl)prop-2-en-1-one
Traditional Namexanthohumol C
SMILESCOC1=C(C(=O)\C=C\C2=CC=C(O)C=C2)C(O)=C2C=CC(C)(C)OC2=C1
InChI IdentifierInChI=1S/C21H20O5/c1-21(2)11-10-15-17(26-21)12-18(25-3)19(20(15)24)16(23)9-6-13-4-7-14(22)8-5-13/h4-12,22,24H,1-3H3/b9-6+
InChI KeyCVMUWVCGBFJJFI-RMKNXTFCSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as 2'-hydroxychalcones. These are organic compounds containing chalcone skeleton that carries a hydroxyl group at the 2'-position.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassLinear 1,3-diarylpropanoids
Sub ClassChalcones and dihydrochalcones
Direct Parent2'-Hydroxychalcones
Alternative Parents
Substituents
  • 2'-hydroxychalcone
  • Hydroxycinnamic acid or derivatives
  • 2,2-dimethyl-1-benzopyran
  • Benzopyran
  • 1-benzopyran
  • Anisole
  • Styrene
  • Aryl ketone
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Acryloyl-group
  • Enone
  • Vinylogous acid
  • Alpha,beta-unsaturated ketone
  • Ketone
  • Organoheterocyclic compound
  • Ether
  • Oxacycle
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0084 g/LALOGPS
logP4.17ALOGPS
logP4.68ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)8.04ChemAxon
pKa (Strongest Basic)-4.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area75.99 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity101.7 m³·mol⁻¹ChemAxon
Polarizability38.28 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-0429000000-e235ce268965e41aede3Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-05ur-4244900000-ee56d20dd991d04414f8Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0019000000-6bbb1e200c58b77789d1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uej-1489000000-38ed5a894a5ebbdaf71dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-4940000000-f77acefd3178df24c7abSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0139000000-d06a83cb63bb0fca4843Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pb9-0696000000-82633902348d0f8f8cfdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014r-0981000000-4318ba91467241c8f441Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0009000000-6e92c793e36e9b62bce6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0490000000-2b9625a88cc3a8bdaaeeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05ox-3950000000-6466939a926e2f4cf084Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0039000000-f1a9d07fa54640c703b6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0339000000-edf7c4563609f50e5b15Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-5902000000-a777b002cf247e687405Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0030234
FooDB IDFDB002056
Phenol Explorer IDNot Available
KNApSAcK IDC00014476
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID8513534
ChEBI ID567477
PubChem Compound ID10338075
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.