Xanthohumol B (CHEM028832)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 00:44:14 UTC
Update Date2016-11-09 01:18:46 UTC
Accession NumberCHEM028832
Identification
Common NameXanthohumol B
ClassSmall Molecule
DescriptionA member of the class of chalcones that is (2E)-1-(3,4-dihydro-2H-chromen-6-yl)-3-(4-hydroxyphenyl)prop-2-en-1-one substituted by hydroxy groups at position 3 and 5, a methoxy group at position 7 and geminal methyl groups at position 2. It has been isolated as a racemate from Humulus lupulus and has been shown to exhibit inhibitory activity against nitric oxide production.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
Dehydrocycloxanthohumol hydrateChEBI
rac-(e)-1-(3,5-Dihydroxy-7-methoxy-2,2-dimethyl-3,4-dihydrochromen-6-yl)-3-(4-hydroxyphenyl)prop-2-en-1-oneChEBI
rac-6'',6''-Dimethyl-5''-hydroxy-4'',5''-dihydropyrano[2'',3'':4',3']-4,2'-dihydroxy-6'-methoxychalconeChEBI
rac-6-[3,4-Dihydro-3,5-dihydroxy-7-methoxy-2,2-dimethyl-2H-benzo[b]pyrano]-3-(4-hydroxyphenyl)-2-propen-1-oneChEBI
Dehydrocycloxanthohumol hydric acidGenerator
6'',6''-Dimethyl-5''-hydroxy-4'',5''-dihydropyrano[2'',3'':4',3']-4,2'-dihydroxy-6'-methoxychalconeHMDB
Chemical FormulaC21H22O6
Average Molecular Mass370.396 g/mol
Monoisotopic Mass370.142 g/mol
CAS Registry Number189308-10-9
IUPAC Name(2E)-1-(3,5-dihydroxy-7-methoxy-2,2-dimethyl-3,4-dihydro-2H-1-benzopyran-6-yl)-3-(4-hydroxyphenyl)prop-2-en-1-one
Traditional Namexanthohumol B
SMILESCOC1=C(C(=O)\C=C\C2=CC=C(O)C=C2)C(O)=C2CC(O)C(C)(C)OC2=C1
InChI IdentifierInChI=1S/C21H22O6/c1-21(2)18(24)10-14-16(27-21)11-17(26-3)19(20(14)25)15(23)9-6-12-4-7-13(22)8-5-12/h4-9,11,18,22,24-25H,10H2,1-3H3/b9-6+
InChI KeyGUQGMEWOCKDLDE-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
  • Chromane
  • Benzopyran
  • 1-benzopyran
  • Anisole
  • Styrene
  • Aryl ketone
  • Alkyl aryl ether
  • Phenol
  • 1-hydroxy-2-unsubstituted benzenoid
  • 1-hydroxy-4-unsubstituted benzenoid
  • Benzenoid
  • Monocyclic benzene moiety
  • Vinylogous acid
  • Alpha,beta-unsaturated ketone
  • Acryloyl-group
  • Enone
  • Secondary alcohol
  • Ketone
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organooxygen compound
  • Alcohol
  • 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 Solubility0.013 g/LALOGPS
logP3.21ALOGPS
logP3.72ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)8.27ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area96.22 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity102.09 m³·mol⁻¹ChemAxon
Polarizability39.71 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, Positivesplash10-0udl-0229000000-b811f90951d1a0a835d1Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-00di-6040190000-bdc2a7531e971d5f1a9dSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0179000000-e2301b1431f4b57e5b7aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0493000000-6468906cb55db17ec732Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-2940000000-8c2ed436d015fefe3a4bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0149000000-423b4abd708a051724efSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00xs-6594000000-22d370d3f79419763d48Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-3590000000-430efc544d480953d59bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0029000000-0be4f2f0792fa82b11b5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0898000000-a197e8c9c81ccea5cecaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-1930000000-bf324f554727d9051fa0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0019000000-7b119b59c36247b7ed5eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f89-1391000000-92e5e602575e67980af7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00su-4962000000-6aa1110047dcb2f70570Spectrum
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 IDHMDB0034867
FooDB IDFDB013439
Phenol Explorer IDNot Available
KNApSAcK IDC00014478
BiGG IDNot Available
BioCyc IDCPD-7127
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID7975271
ChEBI ID66334
PubChem Compound ID9799506
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=10418944
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=10737704
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=15679315
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=9366096
5. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.