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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:53:10 UTC
Update Date2022-03-07 02:53:33 UTC
HMDB IDHMDB0032999
Secondary Accession Numbers
  • HMDB32999
Metabolite Identification
Common Name4-Hydroxyxanthone
Description4-Hydroxyxanthone belongs to the class of organic compounds known as xanthones. These are polycyclic aromatic compounds containing a xanthene moiety conjugated to a ketone group at carbon 9. Xanthene is a tricyclic compound made up of two benzene rings linearly fused to each other through a pyran ring. 4-Hydroxyxanthone has been detected, but not quantified in, fruits. This could make 4-hydroxyxanthone a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on 4-Hydroxyxanthone.
Structure
Data?1563862336
Synonyms
ValueSource
4-Hydroxy-9H-xanthen-9-one, 9ciHMDB
4-HydroxyxanthoneMeSH
Chemical FormulaC13H8O3
Average Molecular Weight212.2008
Monoisotopic Molecular Weight212.047344122
IUPAC Name4-hydroxy-9H-xanthen-9-one
Traditional Name4-hydroxyxanthen-9-one
CAS Registry Number14686-63-6
SMILES
OC1=CC=CC2=C1OC1=CC=CC=C1C2=O
InChI Identifier
InChI=1S/C13H8O3/c14-10-6-3-5-9-12(15)8-4-1-2-7-11(8)16-13(9)10/h1-7,14H
InChI KeyKBQFPPUAIJHDCO-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as xanthones. These are polycyclic aromatic compounds containing a xanthene moiety conjugated to a ketone group at carbon 9. Xanthene is a tricyclic compound made up of two benzene rings linearly fused to each other through a pyran ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzopyrans
Sub Class1-benzopyrans
Direct ParentXanthones
Alternative Parents
Substituents
  • Xanthone
  • Chromone
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Pyranone
  • Benzenoid
  • Pyran
  • Heteroaromatic compound
  • Oxacycle
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point245 - 246 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.34 g/LALOGPS
logP3.04ALOGPS
logP2.66ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)7.9ChemAxon
pKa (Strongest Basic)-6.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity58.8 m³·mol⁻¹ChemAxon
Polarizability21.23 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
DarkChem[M+H]+145.71431661259
DarkChem[M-H]-143.31431661259
DeepCCS[M+H]+139.10530932474
DeepCCS[M-H]-136.71730932474
DeepCCS[M-2H]-171.85830932474
DeepCCS[M+Na]+147.03930932474
AllCCS[M+H]+144.532859911
AllCCS[M+H-H2O]+140.132859911
AllCCS[M+NH4]+148.632859911
AllCCS[M+Na]+149.832859911
AllCCS[M-H]-145.232859911
AllCCS[M+Na-2H]-144.532859911
AllCCS[M+HCOO]-143.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
4-HydroxyxanthoneOC1=CC=CC2=C1OC1=CC=CC=C1C2=O2964.8Standard polar33892256
4-HydroxyxanthoneOC1=CC=CC2=C1OC1=CC=CC=C1C2=O1995.7Standard non polar33892256
4-HydroxyxanthoneOC1=CC=CC2=C1OC1=CC=CC=C1C2=O2037.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
4-Hydroxyxanthone,1TMS,isomer #1C[Si](C)(C)OC1=CC=CC2=C1OC1=CC=CC=C1C2=O2328.1Semi standard non polar33892256
4-Hydroxyxanthone,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=CC2=C1OC1=CC=CC=C1C2=O2547.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 4-Hydroxyxanthone GC-MS (Non-derivatized) - 70eV, Positivesplash10-03e9-3930000000-4f3d69586e891482e9a22017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Hydroxyxanthone GC-MS (1 TMS) - 70eV, Positivesplash10-00yi-9880000000-978e57f00ababcc2b6f52017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Hydroxyxanthone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Hydroxyxanthone 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 - 4-Hydroxyxanthone 10V, Positive-QTOFsplash10-03di-0090000000-ec1d0e2d0ef40c225dc02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxyxanthone 20V, Positive-QTOFsplash10-03di-0090000000-11208d93e3c96a75257b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxyxanthone 40V, Positive-QTOFsplash10-03di-4490000000-700515a0c54bc7b1875e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxyxanthone 10V, Negative-QTOFsplash10-03di-0090000000-c89f4c5b2a83455858142016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxyxanthone 20V, Negative-QTOFsplash10-03di-0090000000-14ebf9afb7484f6784cf2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxyxanthone 40V, Negative-QTOFsplash10-03di-4890000000-ee2455f1ad8691a368b32016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxyxanthone 10V, Positive-QTOFsplash10-03di-0090000000-7d2e191c18d3f0b0ca512021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxyxanthone 20V, Positive-QTOFsplash10-03di-0090000000-7d2e191c18d3f0b0ca512021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxyxanthone 40V, Positive-QTOFsplash10-057i-5900000000-8ae6d022e6108d9b00e72021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxyxanthone 10V, Negative-QTOFsplash10-03di-0090000000-fa5c46c2572ef8a7bf102021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxyxanthone 20V, Negative-QTOFsplash10-03di-0090000000-fa5c46c2572ef8a7bf102021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxyxanthone 40V, Negative-QTOFsplash10-01q9-1920000000-45d249edc9b06f3d0d2c2021-09-23Wishart 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 IDFDB010988
KNApSAcK IDC00042142
Chemspider ID531497
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound611428
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
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.. .