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Showing Compound 1-Hydroxy-3,5-dimethoxy-2,4-diprenylxanthone (FDB021187)

Record Information
Version1.0
Creation date2010-04-08 22:15:32 UTC
Update date2019-11-26 03:20:01 UTC
Primary IDFDB021187
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name1-Hydroxy-3,5-dimethoxy-2,4-diprenylxanthone
Description1-Hydroxy-3,5-dimethoxy-2,4-diprenylxanthone belongs to the class of organic compounds known as 4-prenylated xanthones. These are organic compounds containing a C5-isoprenoid group linked to a xanthone moiety at the 4-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-3,5-dimethoxy-2,4-diprenylxanthone has been detected, but not quantified in, fruits. This could make 1-hydroxy-3,5-dimethoxy-2,4-diprenylxanthone a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 1-Hydroxy-3,5-dimethoxy-2,4-diprenylxanthone.
CAS Number35323-84-3
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
3,5-Di-O-methyl-8-deoxygartaninHMDB
1-Hydroxy-3,5-dimethoxy-2,4-diprenylxanthonedb_source
Predicted Properties
PropertyValueSource
Water Solubility0.0023 g/LALOGPS
logP4.42ALOGPS
logP6.45ChemAxon
logS-5.2ALOGPS
pKa (Strongest Acidic)9.31ChemAxon
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area64.99 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity120.21 m³·mol⁻¹ChemAxon
Polarizability45.88 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC25H28O5
IUPAC name1-hydroxy-3,5-dimethoxy-2,4-bis(3-methylbut-2-en-1-yl)-9H-xanthen-9-one
InChI IdentifierInChI=1S/C25H28O5/c1-14(2)10-12-17-22(27)20-21(26)16-8-7-9-19(28-5)24(16)30-25(20)18(23(17)29-6)13-11-15(3)4/h7-11,27H,12-13H2,1-6H3
InChI KeyKGBJYZXDYBPQGM-UHFFFAOYSA-N
Isomeric SMILESCOC1=CC=CC2=C1OC1=C(C(O)=C(CC=C(C)C)C(OC)=C1CC=C(C)C)C2=O
Average Molecular Weight408.4868
Monoisotopic Molecular Weight408.193674006
Classification
Description Belongs to the class of organic compounds known as 4-prenylated xanthones. These are organic compounds containing a C5-isoprenoid group linked to a xanthone moiety at the 4-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 Parent4-prenylated xanthones
Alternative Parents
Substituents
  • 4-prenylated xanthone
  • 2-prenylated xanthone
  • Chromone
  • Anisole
  • 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
Disposition

Route of exposure:

Biological location:

Source:

Role

Biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 73.51%; H 6.91%; O 19.58%DFC
Melting PointMp 117-118° (106-108°)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
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS1-Hydroxy-3,5-dimethoxy-2,4-diprenylxanthone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0006-1009000000-b0184614ee155d3c54e0Spectrum
Predicted GC-MS1-Hydroxy-3,5-dimethoxy-2,4-diprenylxanthone, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-014i-1001900000-709313d5160287c3a3b8Spectrum
Predicted GC-MS1-Hydroxy-3,5-dimethoxy-2,4-diprenylxanthone, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-1007900000-77a00775a185b5048dd92017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0pvi-7009100000-572c4075eddc542ccb282017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0aor-9025000000-1eb79b9d4bf19d9b9cea2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0001900000-1227b8389ce141bb712c2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0009600000-6ed08bd4a16dd27e36bf2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03kj-0239000000-75d86d1f4187975f0a9e2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0004900000-4c7a1fe197b2a93ca7ce2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0029100000-79aef65e2a7688e0ad732021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001a-0089000000-0fde9221bd7eabb546742021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0000900000-4232e56e7795651b99e42021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0009400000-5150ab3812a26ee02e232021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0h6r-0109100000-17e3cd1eb2719f2eaf632021-09-22View Spectrum
NMRNot Available
ChemSpider ID30777547
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB41275
CRC / DFC (Dictionary of Food Compounds) IDCMS45-C:NMV89-Y
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