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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 19:56:28 UTC
Update Date2022-03-07 02:54:19 UTC
HMDB IDHMDB0035002
Secondary Accession Numbers
  • HMDB35002
Metabolite Identification
Common 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. Xanthogalenol 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 Xanthogalenol.
Structure
Data?1563862649
Synonyms
ValueSource
3' Prenyl-4' O-methylchalconaringeninChEBI
3'-Prenyl-4,2',6'-trihydroxy-4'-methoxychalconeChEBI
2',4,6'-Trihydroxy-4'-methoxy-3'-prenylchalconeHMDB
Chemical FormulaC21H22O5
Average Molecular Weight354.3964
Monoisotopic Molecular Weight354.146723814
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
Traditional Namexanthogalenol
CAS Registry Number265659-35-6
SMILES
COC1=C(CC=C(C)C)C(O)=C(C(=O)\C=C\C2=CC=C(O)C=C2)C(O)=C1
InChI Identifier
InChI=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
Chemical Taxonomy
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
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.11 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+191.46630932474
DeepCCS[M-H]-189.10830932474
DeepCCS[M-2H]-222.59730932474
DeepCCS[M+Na]+197.82630932474
AllCCS[M+H]+187.632859911
AllCCS[M+H-H2O]+184.432859911
AllCCS[M+NH4]+190.632859911
AllCCS[M+Na]+191.532859911
AllCCS[M-H]-185.032859911
AllCCS[M+Na-2H]-184.932859911
AllCCS[M+HCOO]-184.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
XanthogalenolCOC1=C(CC=C(C)C)C(O)=C(C(=O)\C=C\C2=CC=C(O)C=C2)C(O)=C14940.4Standard polar33892256
XanthogalenolCOC1=C(CC=C(C)C)C(O)=C(C(=O)\C=C\C2=CC=C(O)C=C2)C(O)=C13090.5Standard non polar33892256
XanthogalenolCOC1=C(CC=C(C)C)C(O)=C(C(=O)\C=C\C2=CC=C(O)C=C2)C(O)=C13340.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Xanthogalenol,1TMS,isomer #1COC1=CC(O)=C(C(=O)/C=C/C2=CC=C(O)C=C2)C(O[Si](C)(C)C)=C1CC=C(C)C3185.6Semi standard non polar33892256
Xanthogalenol,1TMS,isomer #2COC1=CC(O)=C(C(=O)/C=C/C2=CC=C(O[Si](C)(C)C)C=C2)C(O)=C1CC=C(C)C3169.9Semi standard non polar33892256
Xanthogalenol,1TMS,isomer #3COC1=CC(O[Si](C)(C)C)=C(C(=O)/C=C/C2=CC=C(O)C=C2)C(O)=C1CC=C(C)C3181.3Semi standard non polar33892256
Xanthogalenol,2TMS,isomer #1COC1=CC(O[Si](C)(C)C)=C(C(=O)/C=C/C2=CC=C(O)C=C2)C(O[Si](C)(C)C)=C1CC=C(C)C3144.5Semi standard non polar33892256
Xanthogalenol,2TMS,isomer #2COC1=CC(O)=C(C(=O)/C=C/C2=CC=C(O[Si](C)(C)C)C=C2)C(O[Si](C)(C)C)=C1CC=C(C)C3143.7Semi standard non polar33892256
Xanthogalenol,2TMS,isomer #3COC1=CC(O[Si](C)(C)C)=C(C(=O)/C=C/C2=CC=C(O[Si](C)(C)C)C=C2)C(O)=C1CC=C(C)C3145.2Semi standard non polar33892256
Xanthogalenol,3TMS,isomer #1COC1=CC(O[Si](C)(C)C)=C(C(=O)/C=C/C2=CC=C(O[Si](C)(C)C)C=C2)C(O[Si](C)(C)C)=C1CC=C(C)C3176.1Semi standard non polar33892256
Xanthogalenol,1TBDMS,isomer #1COC1=CC(O)=C(C(=O)/C=C/C2=CC=C(O)C=C2)C(O[Si](C)(C)C(C)(C)C)=C1CC=C(C)C3457.1Semi standard non polar33892256
Xanthogalenol,1TBDMS,isomer #2COC1=CC(O)=C(C(=O)/C=C/C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)C(O)=C1CC=C(C)C3434.7Semi standard non polar33892256
Xanthogalenol,1TBDMS,isomer #3COC1=CC(O[Si](C)(C)C(C)(C)C)=C(C(=O)/C=C/C2=CC=C(O)C=C2)C(O)=C1CC=C(C)C3432.9Semi standard non polar33892256
Xanthogalenol,2TBDMS,isomer #1COC1=CC(O[Si](C)(C)C(C)(C)C)=C(C(=O)/C=C/C2=CC=C(O)C=C2)C(O[Si](C)(C)C(C)(C)C)=C1CC=C(C)C3663.7Semi standard non polar33892256
Xanthogalenol,2TBDMS,isomer #2COC1=CC(O)=C(C(=O)/C=C/C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)C(O[Si](C)(C)C(C)(C)C)=C1CC=C(C)C3677.5Semi standard non polar33892256
Xanthogalenol,2TBDMS,isomer #3COC1=CC(O[Si](C)(C)C(C)(C)C)=C(C(=O)/C=C/C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)C(O)=C1CC=C(C)C3677.9Semi standard non polar33892256
Xanthogalenol,3TBDMS,isomer #1COC1=CC(O[Si](C)(C)C(C)(C)C)=C(C(=O)/C=C/C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)C(O[Si](C)(C)C(C)(C)C)=C1CC=C(C)C3901.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Xanthogalenol GC-MS (Non-derivatized) - 70eV, Positivesplash10-000j-3459000000-8086a86ef04627fc559a2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Xanthogalenol GC-MS (3 TMS) - 70eV, Positivesplash10-0a4i-1001290000-27ebccdf6673fc73908e2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Xanthogalenol 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 - Xanthogalenol 10V, Positive-QTOFsplash10-0a4i-0129000000-836af65cb4ae74175c882016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Xanthogalenol 20V, Positive-QTOFsplash10-05mt-3696000000-ae1e87c202e1b83d37172016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Xanthogalenol 40V, Positive-QTOFsplash10-016r-4910000000-093de7a4a5c7916eede62016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Xanthogalenol 10V, Negative-QTOFsplash10-0udi-0129000000-a92805839c571d453a6e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Xanthogalenol 20V, Negative-QTOFsplash10-0pbd-0955000000-c208ad3f8d4edb90545f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Xanthogalenol 40V, Negative-QTOFsplash10-0avm-1930000000-a40d21950ef93ac5ba5b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Xanthogalenol 10V, Negative-QTOFsplash10-0udi-0009000000-cf0d5b7646fbfcac4d812021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Xanthogalenol 20V, Negative-QTOFsplash10-0udi-0259000000-d59a2bac22530a37d7a62021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Xanthogalenol 40V, Negative-QTOFsplash10-014l-1920000000-b28a071e0b0ec5ee32472021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Xanthogalenol 10V, Positive-QTOFsplash10-0a4j-0429000000-a2c14b4be6145244b0682021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Xanthogalenol 20V, Positive-QTOFsplash10-004i-0931000000-9a041dc31a2b43b191af2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Xanthogalenol 40V, Positive-QTOFsplash10-00or-2911000000-a04ec936ed7cafb4f3cc2021-09-22Wishart 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 IDFDB013606
KNApSAcK IDC00014475
Chemspider ID24692988
KEGG Compound IDNot Available
BioCyc IDCPD-7121
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound14309735
PDB IDNot Available
ChEBI ID136826
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1846881
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.. .