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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 21:45:23 UTC
Update Date2022-03-07 02:54:59 UTC
HMDB IDHMDB0036597
Secondary Accession Numbers
  • HMDB36597
Metabolite Identification
Common Name1-Hydroxy-3,6,7-trimethoxy-2,8-diprenylxanthone
Description1-Hydroxy-3,6,7-trimethoxy-2,8-diprenylxanthone belongs to the class of organic compounds known as 8-prenylated xanthones. These are organic compounds containing a C5-isoprenoid group linked to a xanthone moiety at the 8-position. Xanthone is a tricyclic compound made up of two benzene rings linearly fused to each other through a pyran ring that carries a ketone group. 1-Hydroxy-3,6,7-trimethoxy-2,8-diprenylxanthone has been detected, but not quantified in, fruits. This could make 1-hydroxy-3,6,7-trimethoxy-2,8-diprenylxanthone a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on 1-Hydroxy-3,6,7-trimethoxy-2,8-diprenylxanthone.
Structure
Data?1563862894
Synonyms
ValueSource
Di-O-methylmangostinChEMBL, HMDB
Dimethyl-mangostinHMDB
Fuscaxanthone CHMDB
Chemical FormulaC26H30O6
Average Molecular Weight438.5128
Monoisotopic Molecular Weight438.204238692
IUPAC Name1-hydroxy-3,6,7-trimethoxy-2,8-bis(3-methylbut-2-en-1-yl)-9H-xanthen-9-one
Traditional Name1-hydroxy-3,6,7-trimethoxy-2,8-bis(3-methylbut-2-en-1-yl)xanthen-9-one
CAS Registry Number15404-76-9
SMILES
COC1=CC2=C(C(O)=C1CC=C(C)C)C(=O)C1=C(CC=C(C)C)C(OC)=C(OC)C=C1O2
InChI Identifier
InChI=1S/C26H30O6/c1-14(2)8-10-16-18(29-5)12-20-23(24(16)27)25(28)22-17(11-9-15(3)4)26(31-7)21(30-6)13-19(22)32-20/h8-9,12-13,27H,10-11H2,1-7H3
InChI KeyFCIKYGUVHWZSJV-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 8-prenylated xanthones. These are organic compounds containing a C5-isoprenoid group linked to a xanthone moiety at the 8-position. Xanthone is a tricyclic compound made up of two benzene rings linearly fused to each other through a pyran ring that carries a ketone group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzopyrans
Sub Class1-benzopyrans
Direct Parent8-prenylated xanthones
Alternative Parents
Substituents
  • 2-prenylated xanthone
  • 8-prenylated xanthone
  • Chromone
  • Anisole
  • 1-hydroxy-4-unsubstituted benzenoid
  • Alkyl aryl ether
  • Pyranone
  • Pyran
  • Benzenoid
  • Heteroaromatic compound
  • Vinylogous acid
  • 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 Point120 - 121 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility2.5e-05 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0035 g/LALOGPS
logP4.19ALOGPS
logP6.29ChemAxon
logS-5.1ALOGPS
pKa (Strongest Acidic)9.35ChemAxon
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area74.22 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity126.67 m³·mol⁻¹ChemAxon
Polarizability49.41 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+203.08731661259
DarkChem[M-H]-203.62831661259
DeepCCS[M+H]+202.66330932474
DeepCCS[M-H]-200.30530932474
DeepCCS[M-2H]-233.55830932474
DeepCCS[M+Na]+208.78630932474
AllCCS[M+H]+206.632859911
AllCCS[M+H-H2O]+204.132859911
AllCCS[M+NH4]+208.832859911
AllCCS[M+Na]+209.532859911
AllCCS[M-H]-206.832859911
AllCCS[M+Na-2H]-207.032859911
AllCCS[M+HCOO]-207.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
1-Hydroxy-3,6,7-trimethoxy-2,8-diprenylxanthoneCOC1=CC2=C(C(O)=C1CC=C(C)C)C(=O)C1=C(CC=C(C)C)C(OC)=C(OC)C=C1O25031.8Standard polar33892256
1-Hydroxy-3,6,7-trimethoxy-2,8-diprenylxanthoneCOC1=CC2=C(C(O)=C1CC=C(C)C)C(=O)C1=C(CC=C(C)C)C(OC)=C(OC)C=C1O23570.4Standard non polar33892256
1-Hydroxy-3,6,7-trimethoxy-2,8-diprenylxanthoneCOC1=CC2=C(C(O)=C1CC=C(C)C)C(=O)C1=C(CC=C(C)C)C(OC)=C(OC)C=C1O23588.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
1-Hydroxy-3,6,7-trimethoxy-2,8-diprenylxanthone,1TMS,isomer #1COC1=CC2=C(C(O[Si](C)(C)C)=C1CC=C(C)C)C(=O)C1=C(CC=C(C)C)C(OC)=C(OC)C=C1O23355.6Semi standard non polar33892256
1-Hydroxy-3,6,7-trimethoxy-2,8-diprenylxanthone,1TBDMS,isomer #1COC1=CC2=C(C(O[Si](C)(C)C(C)(C)C)=C1CC=C(C)C)C(=O)C1=C(CC=C(C)C)C(OC)=C(OC)C=C1O23566.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 1-Hydroxy-3,6,7-trimethoxy-2,8-diprenylxanthone GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-1046900000-8a5e4555be06c35920ac2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 1-Hydroxy-3,6,7-trimethoxy-2,8-diprenylxanthone GC-MS (1 TMS) - 70eV, Positivesplash10-0002-1010900000-9b56577085a409653a402017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 1-Hydroxy-3,6,7-trimethoxy-2,8-diprenylxanthone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - 1-Hydroxy-3,6,7-trimethoxy-2,8-diprenylxanthone 20V, Positive-QTOFsplash10-001i-0009000000-bed0a1fefc216a68bb302021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 1-Hydroxy-3,6,7-trimethoxy-2,8-diprenylxanthone 10V, Positive-QTOFsplash10-001i-0009300000-d54545c6326d8672ab872021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 1-Hydroxy-3,6,7-trimethoxy-2,8-diprenylxanthone 40V, Positive-QTOFsplash10-01t9-0049000000-933d6fb8a6dee25568542021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Hydroxy-3,6,7-trimethoxy-2,8-diprenylxanthone 10V, Positive-QTOFsplash10-000i-0005900000-8f21367c9fe85fa06fe32016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Hydroxy-3,6,7-trimethoxy-2,8-diprenylxanthone 20V, Positive-QTOFsplash10-00m0-2009300000-a974a1c6e6a862c9ebee2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Hydroxy-3,6,7-trimethoxy-2,8-diprenylxanthone 40V, Positive-QTOFsplash10-0gb9-5319500000-d6826600480150a05a7f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Hydroxy-3,6,7-trimethoxy-2,8-diprenylxanthone 10V, Negative-QTOFsplash10-000i-0000900000-0989ca1455e6ea8f115e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Hydroxy-3,6,7-trimethoxy-2,8-diprenylxanthone 20V, Negative-QTOFsplash10-0079-0014900000-86ff8be603ff9a5209972016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Hydroxy-3,6,7-trimethoxy-2,8-diprenylxanthone 40V, Negative-QTOFsplash10-00dl-0639200000-98bb4607bf0452c733bd2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Hydroxy-3,6,7-trimethoxy-2,8-diprenylxanthone 10V, Positive-QTOFsplash10-001r-0009500000-4f83109dde19088addad2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Hydroxy-3,6,7-trimethoxy-2,8-diprenylxanthone 20V, Positive-QTOFsplash10-001i-0009100000-c791471279968a909b012021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Hydroxy-3,6,7-trimethoxy-2,8-diprenylxanthone 40V, Positive-QTOFsplash10-014i-0009000000-505520411b0432f8115e2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Hydroxy-3,6,7-trimethoxy-2,8-diprenylxanthone 10V, Negative-QTOFsplash10-000i-0000900000-7a26771424e8ef55073f2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Hydroxy-3,6,7-trimethoxy-2,8-diprenylxanthone 20V, Negative-QTOFsplash10-000i-0003900000-2116bda8a90330f449032021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Hydroxy-3,6,7-trimethoxy-2,8-diprenylxanthone 40V, Negative-QTOFsplash10-0udr-0129200000-8f1d859630e93fc2247b2021-09-24Wishart 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 IDFDB015509
KNApSAcK IDC00034845
Chemspider ID201624
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound231412
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1855851
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.. .