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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 19:47:45 UTC
Update Date2022-03-07 02:54:15 UTC
HMDB IDHMDB0034867
Secondary Accession Numbers
  • HMDB34867
Metabolite Identification
Common NameXanthohumol B
DescriptionXanthohumol B 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. Thus, xanthohumol b is considered to be a flavonoid. Xanthohumol B has been detected, but not quantified in, a few different foods, such as alcoholic beverages, breakfast cereal, and cereals and cereal products. This could make xanthohumol b a potential biomarker for the consumption of these foods. Xanthohumol B is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a small amount of articles have been published on Xanthohumol B.
Structure
Data?1563862627
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 Weight370.3958
Monoisotopic Molecular Weight370.141638436
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
CAS Registry Number189308-10-9
SMILES
COC1=C(C(=O)\C=C\C2=CC=C(O)C=C2)C(O)=C2CC(O)C(C)(C)OC2=C1
InChI Identifier
InChI=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
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility27.04 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+189.65730932474
DeepCCS[M-H]-187.26130932474
DeepCCS[M-2H]-220.75430932474
DeepCCS[M+Na]+195.95530932474
AllCCS[M+H]+191.632859911
AllCCS[M+H-H2O]+188.532859911
AllCCS[M+NH4]+194.432859911
AllCCS[M+Na]+195.232859911
AllCCS[M-H]-191.932859911
AllCCS[M+Na-2H]-192.132859911
AllCCS[M+HCOO]-192.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Xanthohumol BCOC1=C(C(=O)\C=C\C2=CC=C(O)C=C2)C(O)=C2CC(O)C(C)(C)OC2=C14903.4Standard polar33892256
Xanthohumol BCOC1=C(C(=O)\C=C\C2=CC=C(O)C=C2)C(O)=C2CC(O)C(C)(C)OC2=C13252.8Standard non polar33892256
Xanthohumol BCOC1=C(C(=O)\C=C\C2=CC=C(O)C=C2)C(O)=C2CC(O)C(C)(C)OC2=C13606.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Xanthohumol B,1TMS,isomer #1COC1=CC2=C(CC(O)C(C)(C)O2)C(O)=C1C(=O)/C=C/C1=CC=C(O[Si](C)(C)C)C=C13322.8Semi standard non polar33892256
Xanthohumol B,1TMS,isomer #2COC1=CC2=C(CC(O)C(C)(C)O2)C(O[Si](C)(C)C)=C1C(=O)/C=C/C1=CC=C(O)C=C13304.5Semi standard non polar33892256
Xanthohumol B,1TMS,isomer #3COC1=CC2=C(CC(O[Si](C)(C)C)C(C)(C)O2)C(O)=C1C(=O)/C=C/C1=CC=C(O)C=C13256.7Semi standard non polar33892256
Xanthohumol B,2TMS,isomer #1COC1=CC2=C(CC(O)C(C)(C)O2)C(O[Si](C)(C)C)=C1C(=O)/C=C/C1=CC=C(O[Si](C)(C)C)C=C13285.6Semi standard non polar33892256
Xanthohumol B,2TMS,isomer #2COC1=CC2=C(CC(O[Si](C)(C)C)C(C)(C)O2)C(O)=C1C(=O)/C=C/C1=CC=C(O[Si](C)(C)C)C=C13229.9Semi standard non polar33892256
Xanthohumol B,2TMS,isomer #3COC1=CC2=C(CC(O[Si](C)(C)C)C(C)(C)O2)C(O[Si](C)(C)C)=C1C(=O)/C=C/C1=CC=C(O)C=C13195.5Semi standard non polar33892256
Xanthohumol B,3TMS,isomer #1COC1=CC2=C(CC(O[Si](C)(C)C)C(C)(C)O2)C(O[Si](C)(C)C)=C1C(=O)/C=C/C1=CC=C(O[Si](C)(C)C)C=C13217.1Semi standard non polar33892256
Xanthohumol B,1TBDMS,isomer #1COC1=CC2=C(CC(O)C(C)(C)O2)C(O)=C1C(=O)/C=C/C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C13586.5Semi standard non polar33892256
Xanthohumol B,1TBDMS,isomer #2COC1=CC2=C(CC(O)C(C)(C)O2)C(O[Si](C)(C)C(C)(C)C)=C1C(=O)/C=C/C1=CC=C(O)C=C13562.5Semi standard non polar33892256
Xanthohumol B,1TBDMS,isomer #3COC1=CC2=C(CC(O[Si](C)(C)C(C)(C)C)C(C)(C)O2)C(O)=C1C(=O)/C=C/C1=CC=C(O)C=C13516.7Semi standard non polar33892256
Xanthohumol B,2TBDMS,isomer #1COC1=CC2=C(CC(O)C(C)(C)O2)C(O[Si](C)(C)C(C)(C)C)=C1C(=O)/C=C/C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C13801.2Semi standard non polar33892256
Xanthohumol B,2TBDMS,isomer #2COC1=CC2=C(CC(O[Si](C)(C)C(C)(C)C)C(C)(C)O2)C(O)=C1C(=O)/C=C/C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C13780.8Semi standard non polar33892256
Xanthohumol B,2TBDMS,isomer #3COC1=CC2=C(CC(O[Si](C)(C)C(C)(C)C)C(C)(C)O2)C(O[Si](C)(C)C(C)(C)C)=C1C(=O)/C=C/C1=CC=C(O)C=C13690.1Semi standard non polar33892256
Xanthohumol B,3TBDMS,isomer #1COC1=CC2=C(CC(O[Si](C)(C)C(C)(C)C)C(C)(C)O2)C(O[Si](C)(C)C(C)(C)C)=C1C(=O)/C=C/C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C13957.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Xanthohumol B GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udl-0229000000-b811f90951d1a0a835d12017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Xanthohumol B GC-MS (3 TMS) - 70eV, Positivesplash10-00di-6040190000-bdc2a7531e971d5f1a9d2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Xanthohumol B GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Xanthohumol B 10V, Positive-QTOFsplash10-00di-0179000000-e2301b1431f4b57e5b7a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Xanthohumol B 20V, Positive-QTOFsplash10-0002-0493000000-6468906cb55db17ec7322016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Xanthohumol B 40V, Positive-QTOFsplash10-014i-2940000000-8c2ed436d015fefe3a4b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Xanthohumol B 10V, Negative-QTOFsplash10-014i-0149000000-423b4abd708a051724ef2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Xanthohumol B 20V, Negative-QTOFsplash10-00xs-6594000000-22d370d3f79419763d482016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Xanthohumol B 40V, Negative-QTOFsplash10-014i-3590000000-430efc544d480953d59b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Xanthohumol B 10V, Negative-QTOFsplash10-014i-0029000000-0be4f2f0792fa82b11b52021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Xanthohumol B 20V, Negative-QTOFsplash10-014i-0898000000-a197e8c9c81ccea5ceca2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Xanthohumol B 40V, Negative-QTOFsplash10-014i-1930000000-bf324f554727d9051fa02021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Xanthohumol B 10V, Positive-QTOFsplash10-00di-0019000000-7b119b59c36247b7ed5e2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Xanthohumol B 20V, Positive-QTOFsplash10-0f89-1391000000-92e5e602575e67980af72021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Xanthohumol B 40V, Positive-QTOFsplash10-00su-4962000000-6aa1110047dcb2f705702021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB013439
KNApSAcK IDC00014478
Chemspider ID7975271
KEGG Compound IDNot Available
BioCyc IDCPD-7127
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound9799506
PDB IDNot Available
ChEBI ID66334
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1846021
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .