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Showing Compound Isoxanthohumol (FDB012290)

Record Information
Version1.0
Creation date2010-04-08 22:10:05 UTC
Update date2025-11-18 23:35:31 UTC
Primary IDFDB012290
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameIsoxanthohumol
DescriptionIsoxanthohumol belongs to the class of organic compounds known as 8-prenylated flavanones. These are flavanones that features a C5-isoprenoid substituent at the 8-position. Thus, isoxanthohumol is considered to be a flavonoid lipid molecule. Isoxanthohumol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Isoxanthohumol is a bitter tasting compound. Isoxanthohumol is found, on average, in the highest concentration within beers. Isoxanthohumol has also been detected, but not quantified in, alcoholic beverages. This could make isoxanthohumol a potential biomarker for the consumption of these foods.
CAS Number70872-29-6
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
4',7-Dihydroxy-5-methoxy-8-prenylflavanoneHMDB
5-Methyl-8-prenylnaringeninHMDB
7,4'-Dihydroxy-5-methoxy-8-prenylflavanoneHMDB
IsoxanthohumolMeSH
Predicted Properties
PropertyValueSource
Water Solubility0.014 g/LALOGPS
logP3.25ALOGPS
logP4.06ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)7.66ChemAxon
pKa (Strongest Basic)-4.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area75.99 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity100.01 m³·mol⁻¹ChemAxon
Polarizability38.4 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC21H22O5
IUPAC name7-hydroxy-2-(4-hydroxyphenyl)-5-methoxy-8-(3-methylbut-2-en-1-yl)-3,4-dihydro-2H-1-benzopyran-4-one
InChI IdentifierInChI=1S/C21H22O5/c1-12(2)4-9-15-16(23)10-19(25-3)20-17(24)11-18(26-21(15)20)13-5-7-14(22)8-6-13/h4-8,10,18,22-23H,9,11H2,1-3H3
InChI KeyYKGCBLWILMDSAV-UHFFFAOYSA-N
Isomeric SMILESCOC1=C2C(=O)CC(OC2=C(CC=C(C)C)C(O)=C1)C1=CC=C(O)C=C1
Average Molecular Weight354.402
Monoisotopic Molecular Weight354.146723808
Classification
Description Belongs to the class of organic compounds known as 8-prenylated flavanones. These are flavanones that features a C5-isoprenoid substituent at the 8-position.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavans
Direct Parent8-prenylated flavanones
Alternative Parents
Substituents
  • 8-prenylated flavanone
  • 5-methoxyflavonoid-skeleton
  • 4'-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Hydroxyflavonoid
  • Flavanone
  • Chromone
  • Chromane
  • 1-benzopyran
  • Benzopyran
  • Anisole
  • Aryl alkyl ketone
  • Aryl ketone
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Ketone
  • Organoheterocyclic compound
  • Oxacycle
  • Ether
  • Organooxygen compound
  • Organic oxide
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Role

Biological role:

Foods

Beverages:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 71.17%; H 6.26%; O 22.57%DFC
Melting PointMp 204-206°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]15D -21.5 (c, 0.9 in MeOH)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSIsoxanthohumol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-01rf-2119000000-96b52fb9dc42ebbfa47bSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-03di-0029000000-822a5c98f0e459a8a3dd2017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-014i-0910000000-174cfdea3730598890e02017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-014i-0910000000-174cfdea3730598890e02017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-014i-0910000000-174cfdea3730598890e02017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-000i-0190300000-c8b52269c348affd5c4d2017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-014i-0940000000-563e589b151a0bfb9b742017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-0udi-0009000000-a1136c004783e9a0c59e2017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-0udi-0009000000-013f7e3252ca095b2f722017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-014i-0910000000-174cfdea3730598890e02017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-001i-0392000000-6f77bde5094fc814ffc52017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-0a4i-0000900000-05176f8611780234a3c82017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-0a4i-0000900000-1ee7c4358367fc905ce12017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-0a4i-0000900000-e3db5d38ef786822b6632017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-000i-0190300000-c8b52269c348affd5c4d2017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-014i-0940000000-563e589b151a0bfb9b742017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-0udi-0009000000-a1136c004783e9a0c59e2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-014i-0910000000-174cfdea3730598890e02017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-001i-0392000000-6f77bde5094fc814ffc52017-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0129000000-e7effc727a62fb0c06ba2015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0670-3595000000-03d8297844e813d1214f2015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01di-3911000000-bdee1ff10617374c4d552015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0019000000-3763089b5a0bbecb91bb2015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udr-1249000000-5738ef92f6f39e82b6d82015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00r6-2911000000-30d43c5d0b64b932f6bc2015-04-25View Spectrum
NMRNot Available
ChemSpider ID447736
ChEMBL IDCHEMBL492828
KEGG Compound IDNot Available
Pubchem Compound ID513197
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID224
DrugBank IDNot Available
HMDB IDHMDB34048
CRC / DFC (Dictionary of Food Compounds) IDKRN34-S:HFR45-D
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDC00008246
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
Flavours
FlavorCitations
bitter
  1. Ayana Wiener, Marina Shudler, Anat Levit, Masha Y. Niv. BitterDB: a database of bitter compounds. Nucleic Acids Res 2012, 40(Database issue):D413-419. DOI:10.1093/nar/gkr755
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.