Record Information
Version1.0
Creation date2010-04-08 22:10:11 UTC
Update date2019-11-26 03:06:52 UTC
Primary IDFDB012475
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name1,5,8-Trihydroxy-3-methyl-2-prenylxanthone
Description1,5,8-Trihydroxy-3-methyl-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. 1,5,8-Trihydroxy-3-methyl-2-prenylxanthone is an extremely weak basic (essentially neutral) compound (based on its pKa). 1,5,8-Trihydroxy-3-methyl-2-prenylxanthone has been detected, but not quantified in, fruits. This could make 1,5,8-trihydroxy-3-methyl-2-prenylxanthone a potential biomarker for the consumption of these foods.
CAS Number110187-11-6
Structure
Thumb
Synonyms
SynonymSource
1,5,8-Trihydroxy-3-methyl-2-prenylxanthonedb_source
Predicted Properties
PropertyValueSource
Water Solubility0.042 g/LALOGPS
logP3.38ALOGPS
logP4.92ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)8.36ChemAxon
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area96.22 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity93.46 m³·mol⁻¹ChemAxon
Polarizability35.69 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC19H18O6
IUPAC name1,5,8-trihydroxy-3-methoxy-2-(3-methylbut-2-en-1-yl)-9H-xanthen-9-one
InChI IdentifierInChI=1S/C19H18O6/c1-9(2)4-5-10-13(24-3)8-14-16(17(10)22)18(23)15-11(20)6-7-12(21)19(15)25-14/h4,6-8,20-22H,5H2,1-3H3
InChI KeyAAANZTDKTFGJLZ-UHFFFAOYSA-N
Isomeric SMILESCOC1=CC2=C(C(O)=C1CC=C(C)C)C(=O)C1=C(O)C=CC(O)=C1O2
Average Molecular Weight342.3426
Monoisotopic Molecular Weight342.110338308
Classification
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
  • 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
Disposition

Route of exposure:

Biological location:

Source:

Role

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 66.66%; H 5.30%; O 28.04%DFC
Melting PointMp 193-195°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03di-1059000000-7ed81e522bc787c6a352JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0006-2610590000-ec556141b5e644d068eaJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0019000000-1fa074d70d9270f31d4fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00ku-4089000000-e5719a53d70025d03770JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-6590000000-9c152b5de2e904dbabebJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0009000000-e0eebe168fb718d7da92JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0129000000-8f0d2836faae10b3c637JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4r-2941000000-1f2ecfea54c02293870eJSpectraViewer
ChemSpider ID28295232
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID14162674
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB34182
CRC / DFC (Dictionary of Food Compounds) IDHHG46-P:HHG14-E
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference