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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 02:57:38 UTC
Update Date2022-03-07 02:56:57 UTC
HMDB IDHMDB0041290
Secondary Accession Numbers
  • HMDB41290
Metabolite Identification
Common Name1,8-Dihydroxy-3,5-dimethoxy-2-prenylxanthone
Description1,8-Dihydroxy-3,5-dimethoxy-2-prenylxanthone belongs to the class of organic compounds known as 2-prenylated xanthones. These are organic compounds containing a C5-isoprenoid group linked to a xanthone moiety at the 2-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. 1,8-Dihydroxy-3,5-dimethoxy-2-prenylxanthone has been detected, but not quantified in, fruits. This could make 1,8-dihydroxy-3,5-dimethoxy-2-prenylxanthone a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 1,8-Dihydroxy-3,5-dimethoxy-2-prenylxanthone.
Structure
Data?1563863646
SynonymsNot Available
Chemical FormulaC20H20O6
Average Molecular Weight356.3692
Monoisotopic Molecular Weight356.125988372
IUPAC Name1,8-dihydroxy-3,5-dimethoxy-2-(3-methylbut-2-en-1-yl)-9H-xanthen-9-one
Traditional Name1,8-dihydroxy-3,5-dimethoxy-2-(3-methylbut-2-en-1-yl)xanthen-9-one
CAS Registry Number132031-40-4
SMILES
COC1=CC2=C(C(O)=C1CC=C(C)C)C(=O)C1=C(O)C=CC(OC)=C1O2
InChI Identifier
InChI=1S/C20H20O6/c1-10(2)5-6-11-14(25-4)9-15-17(18(11)22)19(23)16-12(21)7-8-13(24-3)20(16)26-15/h5,7-9,21-22H,6H2,1-4H3
InChI KeyGRYVOCRJTSCVJS-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 2-prenylated xanthones. These are organic compounds containing a C5-isoprenoid group linked to a xanthone moiety at the 2-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 Parent2-prenylated xanthones
Alternative Parents
Substituents
  • 2-prenylated xanthone
  • Chromone
  • Anisole
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Pyranone
  • Benzenoid
  • Pyran
  • Heteroaromatic compound
  • Vinylogous acid
  • Ether
  • Oxacycle
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • 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 Point178 - 181 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.028 g/LALOGPS
logP3.45ALOGPS
logP5.07ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)9.23ChemAxon
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area85.22 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity97.95 m³·mol⁻¹ChemAxon
Polarizability37.72 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+185.64531661259
DarkChem[M-H]-185.46931661259
DeepCCS[M+H]+183.43730932474
DeepCCS[M-H]-181.07930932474
DeepCCS[M-2H]-215.17430932474
DeepCCS[M+Na]+190.40130932474
AllCCS[M+H]+184.132859911
AllCCS[M+H-H2O]+181.032859911
AllCCS[M+NH4]+187.132859911
AllCCS[M+Na]+187.932859911
AllCCS[M-H]-186.832859911
AllCCS[M+Na-2H]-186.432859911
AllCCS[M+HCOO]-186.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
1,8-Dihydroxy-3,5-dimethoxy-2-prenylxanthoneCOC1=CC2=C(C(O)=C1CC=C(C)C)C(=O)C1=C(O)C=CC(OC)=C1O24818.0Standard polar33892256
1,8-Dihydroxy-3,5-dimethoxy-2-prenylxanthoneCOC1=CC2=C(C(O)=C1CC=C(C)C)C(=O)C1=C(O)C=CC(OC)=C1O23164.5Standard non polar33892256
1,8-Dihydroxy-3,5-dimethoxy-2-prenylxanthoneCOC1=CC2=C(C(O)=C1CC=C(C)C)C(=O)C1=C(O)C=CC(OC)=C1O23141.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
1,8-Dihydroxy-3,5-dimethoxy-2-prenylxanthone,1TMS,isomer #1COC1=CC2=C(C(O[Si](C)(C)C)=C1CC=C(C)C)C(=O)C1=C(O)C=CC(OC)=C1O23092.6Semi standard non polar33892256
1,8-Dihydroxy-3,5-dimethoxy-2-prenylxanthone,1TMS,isomer #2COC1=CC2=C(C(O)=C1CC=C(C)C)C(=O)C1=C(O[Si](C)(C)C)C=CC(OC)=C1O23181.8Semi standard non polar33892256
1,8-Dihydroxy-3,5-dimethoxy-2-prenylxanthone,2TMS,isomer #1COC1=CC2=C(C(O[Si](C)(C)C)=C1CC=C(C)C)C(=O)C1=C(O[Si](C)(C)C)C=CC(OC)=C1O23064.8Semi standard non polar33892256
1,8-Dihydroxy-3,5-dimethoxy-2-prenylxanthone,1TBDMS,isomer #1COC1=CC2=C(C(O[Si](C)(C)C(C)(C)C)=C1CC=C(C)C)C(=O)C1=C(O)C=CC(OC)=C1O23305.1Semi standard non polar33892256
1,8-Dihydroxy-3,5-dimethoxy-2-prenylxanthone,1TBDMS,isomer #2COC1=CC2=C(C(O)=C1CC=C(C)C)C(=O)C1=C(O[Si](C)(C)C(C)(C)C)C=CC(OC)=C1O23365.1Semi standard non polar33892256
1,8-Dihydroxy-3,5-dimethoxy-2-prenylxanthone,2TBDMS,isomer #1COC1=CC2=C(C(O[Si](C)(C)C(C)(C)C)=C1CC=C(C)C)C(=O)C1=C(O[Si](C)(C)C(C)(C)C)C=CC(OC)=C1O23505.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 1,8-Dihydroxy-3,5-dimethoxy-2-prenylxanthone GC-MS (Non-derivatized) - 70eV, Positivesplash10-004l-1029000000-b7c2496456f27eb603042017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 1,8-Dihydroxy-3,5-dimethoxy-2-prenylxanthone GC-MS (2 TMS) - 70eV, Positivesplash10-002r-4041900000-2dd90e032128345cb0d22017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 1,8-Dihydroxy-3,5-dimethoxy-2-prenylxanthone 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 - 1,8-Dihydroxy-3,5-dimethoxy-2-prenylxanthone 10V, Positive-QTOFsplash10-0a4i-0009000000-6a3eb408174b5102eccf2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,8-Dihydroxy-3,5-dimethoxy-2-prenylxanthone 20V, Positive-QTOFsplash10-0a4i-6019000000-9341348c54229d9056812017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,8-Dihydroxy-3,5-dimethoxy-2-prenylxanthone 40V, Positive-QTOFsplash10-0690-9332000000-868ebac6ab0b4ee0e9b02017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,8-Dihydroxy-3,5-dimethoxy-2-prenylxanthone 10V, Negative-QTOFsplash10-0a4i-0009000000-2931648c0560f63a6ac22017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,8-Dihydroxy-3,5-dimethoxy-2-prenylxanthone 20V, Negative-QTOFsplash10-0a4r-0019000000-139017faea8bc47941112017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,8-Dihydroxy-3,5-dimethoxy-2-prenylxanthone 40V, Negative-QTOFsplash10-0ap0-2795000000-36210134160cb6f5fae52017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,8-Dihydroxy-3,5-dimethoxy-2-prenylxanthone 10V, Positive-QTOFsplash10-0pb9-0009000000-3beffb41b3cfd233d7362021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,8-Dihydroxy-3,5-dimethoxy-2-prenylxanthone 20V, Positive-QTOFsplash10-0udi-0019000000-5ef77979d944d18e179a2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,8-Dihydroxy-3,5-dimethoxy-2-prenylxanthone 40V, Positive-QTOFsplash10-0uk9-0291000000-41e7e616b50594f71c502021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,8-Dihydroxy-3,5-dimethoxy-2-prenylxanthone 10V, Negative-QTOFsplash10-0a4i-0009000000-0a6526e745d11b23421e2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,8-Dihydroxy-3,5-dimethoxy-2-prenylxanthone 20V, Negative-QTOFsplash10-0a4i-0009000000-48e7c9dd6333308d504e2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,8-Dihydroxy-3,5-dimethoxy-2-prenylxanthone 40V, Negative-QTOFsplash10-0zfr-1379000000-bfc2eaa46965c99ed1a52021-09-25Wishart 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 IDFDB021207
KNApSAcK IDNot Available
Chemspider ID30777549
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound14777481
PDB IDNot Available
ChEBI ID175576
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.. .