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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 02:54:49 UTC
Update Date2022-03-07 02:56:56 UTC
HMDB IDHMDB0041243
Secondary Accession Numbers
  • HMDB41243
Metabolite Identification
Common Name1,3,6-Trihydroxy-5-methoxyxanthone
Description1,3,6-Trihydroxy-5-methoxyxanthone 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. 1,3,6-Trihydroxy-5-methoxyxanthone has been detected, but not quantified in, fruits. This could make 1,3,6-trihydroxy-5-methoxyxanthone a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 1,3,6-Trihydroxy-5-methoxyxanthone.
Structure
Data?1563863641
SynonymsNot Available
Chemical FormulaC14H10O6
Average Molecular Weight274.2256
Monoisotopic Molecular Weight274.047738052
IUPAC Name1,3,6-trihydroxy-5-methoxy-9H-xanthen-9-one
Traditional Name1,3,6-trihydroxy-5-methoxyxanthen-9-one
CAS Registry Number41357-84-0
SMILES
COC1=C(O)C=CC2=C1OC1=CC(O)=CC(O)=C1C2=O
InChI Identifier
InChI=1S/C14H10O6/c1-19-14-8(16)3-2-7-12(18)11-9(17)4-6(15)5-10(11)20-13(7)14/h2-5,15-17H,1H3
InChI KeyOIDDYVZHNYQRKQ-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
  • Anisole
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Pyranone
  • Pyran
  • Benzenoid
  • Heteroaromatic compound
  • Vinylogous acid
  • Polyol
  • Ether
  • Oxacycle
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • 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 Point290 - 291 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.38 g/LALOGPS
logP2.52ALOGPS
logP2.54ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)7.46ChemAxon
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area96.22 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity69.22 m³·mol⁻¹ChemAxon
Polarizability26.11 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]+161.6931661259
DarkChem[M-H]-160.77831661259
DeepCCS[M+H]+158.23330932474
DeepCCS[M-H]-155.87530932474
DeepCCS[M-2H]-188.76130932474
DeepCCS[M+Na]+164.32630932474
AllCCS[M+H]+159.532859911
AllCCS[M+H-H2O]+155.732859911
AllCCS[M+NH4]+163.132859911
AllCCS[M+Na]+164.232859911
AllCCS[M-H]-159.932859911
AllCCS[M+Na-2H]-159.132859911
AllCCS[M+HCOO]-158.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
1,3,6-Trihydroxy-5-methoxyxanthoneCOC1=C(O)C=CC2=C1OC1=CC(O)=CC(O)=C1C2=O4348.3Standard polar33892256
1,3,6-Trihydroxy-5-methoxyxanthoneCOC1=C(O)C=CC2=C1OC1=CC(O)=CC(O)=C1C2=O2795.6Standard non polar33892256
1,3,6-Trihydroxy-5-methoxyxanthoneCOC1=C(O)C=CC2=C1OC1=CC(O)=CC(O)=C1C2=O2769.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
1,3,6-Trihydroxy-5-methoxyxanthone,1TMS,isomer #1COC1=C(O[Si](C)(C)C)C=CC2=C1OC1=CC(O)=CC(O)=C1C2=O2871.9Semi standard non polar33892256
1,3,6-Trihydroxy-5-methoxyxanthone,1TMS,isomer #2COC1=C(O)C=CC2=C1OC1=CC(O[Si](C)(C)C)=CC(O)=C1C2=O2872.0Semi standard non polar33892256
1,3,6-Trihydroxy-5-methoxyxanthone,1TMS,isomer #3COC1=C(O)C=CC2=C1OC1=CC(O)=CC(O[Si](C)(C)C)=C1C2=O2854.5Semi standard non polar33892256
1,3,6-Trihydroxy-5-methoxyxanthone,2TMS,isomer #1COC1=C(O[Si](C)(C)C)C=CC2=C1OC1=CC(O)=CC(O[Si](C)(C)C)=C1C2=O2802.1Semi standard non polar33892256
1,3,6-Trihydroxy-5-methoxyxanthone,2TMS,isomer #2COC1=C(O[Si](C)(C)C)C=CC2=C1OC1=CC(O[Si](C)(C)C)=CC(O)=C1C2=O2841.9Semi standard non polar33892256
1,3,6-Trihydroxy-5-methoxyxanthone,2TMS,isomer #3COC1=C(O)C=CC2=C1OC1=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C1C2=O2883.5Semi standard non polar33892256
1,3,6-Trihydroxy-5-methoxyxanthone,3TMS,isomer #1COC1=C(O[Si](C)(C)C)C=CC2=C1OC1=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C1C2=O2827.5Semi standard non polar33892256
1,3,6-Trihydroxy-5-methoxyxanthone,1TBDMS,isomer #1COC1=C(O[Si](C)(C)C(C)(C)C)C=CC2=C1OC1=CC(O)=CC(O)=C1C2=O3133.7Semi standard non polar33892256
1,3,6-Trihydroxy-5-methoxyxanthone,1TBDMS,isomer #2COC1=C(O)C=CC2=C1OC1=CC(O[Si](C)(C)C(C)(C)C)=CC(O)=C1C2=O3128.1Semi standard non polar33892256
1,3,6-Trihydroxy-5-methoxyxanthone,1TBDMS,isomer #3COC1=C(O)C=CC2=C1OC1=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C1C2=O3097.9Semi standard non polar33892256
1,3,6-Trihydroxy-5-methoxyxanthone,2TBDMS,isomer #1COC1=C(O[Si](C)(C)C(C)(C)C)C=CC2=C1OC1=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C1C2=O3267.8Semi standard non polar33892256
1,3,6-Trihydroxy-5-methoxyxanthone,2TBDMS,isomer #2COC1=C(O[Si](C)(C)C(C)(C)C)C=CC2=C1OC1=CC(O[Si](C)(C)C(C)(C)C)=CC(O)=C1C2=O3318.6Semi standard non polar33892256
1,3,6-Trihydroxy-5-methoxyxanthone,2TBDMS,isomer #3COC1=C(O)C=CC2=C1OC1=CC(O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C1C2=O3344.7Semi standard non polar33892256
1,3,6-Trihydroxy-5-methoxyxanthone,3TBDMS,isomer #1COC1=C(O[Si](C)(C)C(C)(C)C)C=CC2=C1OC1=CC(O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C1C2=O3510.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 1,3,6-Trihydroxy-5-methoxyxanthone GC-MS (Non-derivatized) - 70eV, Positivesplash10-007k-0490000000-ec90b4cee64481d0a5202017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 1,3,6-Trihydroxy-5-methoxyxanthone GC-MS (3 TMS) - 70eV, Positivesplash10-016r-2031900000-5edf8e9191b4bc701b402017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 1,3,6-Trihydroxy-5-methoxyxanthone 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 - 1,3,6-Trihydroxy-5-methoxyxanthone 10V, Positive-QTOFsplash10-004i-0090000000-9d509f3c3eb72f2444dd2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,3,6-Trihydroxy-5-methoxyxanthone 20V, Positive-QTOFsplash10-004i-0090000000-721687af8141622380e82017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,3,6-Trihydroxy-5-methoxyxanthone 40V, Positive-QTOFsplash10-0zfr-3290000000-6601f8ec987cf42b6a102017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,3,6-Trihydroxy-5-methoxyxanthone 10V, Negative-QTOFsplash10-00di-0090000000-f58cbaa21ce916d45d812017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,3,6-Trihydroxy-5-methoxyxanthone 20V, Negative-QTOFsplash10-00di-0090000000-82e3823a7060a37c54772017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,3,6-Trihydroxy-5-methoxyxanthone 40V, Negative-QTOFsplash10-0ufr-0490000000-08dcba5e22a8d05f452e2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,3,6-Trihydroxy-5-methoxyxanthone 10V, Positive-QTOFsplash10-004i-0090000000-889d6786b5fde891f4cd2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,3,6-Trihydroxy-5-methoxyxanthone 20V, Positive-QTOFsplash10-004i-0090000000-889d6786b5fde891f4cd2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,3,6-Trihydroxy-5-methoxyxanthone 40V, Positive-QTOFsplash10-0zgi-0290000000-7a0846a8ebf406c399172021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,3,6-Trihydroxy-5-methoxyxanthone 10V, Negative-QTOFsplash10-00di-0090000000-52b97824b3baf812bc0a2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,3,6-Trihydroxy-5-methoxyxanthone 20V, Negative-QTOFsplash10-00di-0090000000-a29644428860e488f6e32021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,3,6-Trihydroxy-5-methoxyxanthone 40V, Negative-QTOFsplash10-0zfr-0190000000-b5b0732915b511f0f3722021-09-25Wishart 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 IDFDB021151
KNApSAcK IDC00032586
Chemspider ID4591590
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5493675
PDB IDNot Available
ChEBI ID174597
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.. .