Record Information
Version1.0
Creation date2010-04-08 22:05:02 UTC
Update date2019-11-26 02:56:36 UTC
Primary IDFDB001604
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameXanthosine
DescriptionBiological Source: Production by guanine-free mutants of bacteria e.g. Bacillus subtilis, Aerobacter aerogenesand is also reported from seeds of Trifolium alexandrinum Physical Description: Prismatic cryst. (H2O) (Chemnetbase) The deamination product of guanosine; Xanthosine monophosphate is an intermediate in purine metabolism, formed from IMP, and forming GMP.; Xanthylic acid can be used in quantitative measurements of the Inosine monophosphate dehydrogenase enzyme activities in purine metabolism, as recommended to ensure optimal thiopurine therapy for children with acute lymphoblastic leukaemia (ALL). (PMID: 16725387). Xanthosine is found in many foods, some of which are calabash, rambutan, apricot, and pecan nut.
CAS Number146-80-5
Structure
Thumb
Synonyms
SynonymSource
β-D-Ribofuranoside, xanthine-9biospider
1H-Purine-2,6-dione, 3, 9-dihydro-9-β-D-ribofuranosyl-biospider
1H-Purine-2,6-dione, 3,9-dihydro-9-beta-D-ribofuranosyl-biospider
3,9-Dihydro-9-b-D-ribofuranosyl-1H-purine-2,6-dionebiospider
3,9-Dihydro-9-beta-delta-ribofuranosyl-1H-purine-2,6-dionebiospider
3,9-Dihydro-9-D-ribofuranosyl-1H-purine-2,6-dionebiospider
3,9-Dihydro-9-delta-ribofuranosyl-1H-purine-2,6-dionebiospider
9-β-D-Ribofuranosylxanthinebiospider
9-b-D-Ribofuranosylxanthinebiospider
9-beta-D-ribofuranosyl-3,9-dihydro-1H-purine-2,6-dionebiospider
9-beta-D-Ribofuranosylxanthinebiospider
9-beta-delta-Ribofuranosylxanthinebiospider
9-D-Ribofuranosylxanthinebiospider
9-delta-Ribofuranosylxanthinebiospider
beta-D-Ribofuranoside, xanthine-9biospider
Xanthine ribosidebiospider
Predicted Properties
PropertyValueSource
Water Solubility27.8 g/LALOGPS
logP-1.6ALOGPS
logP-1.2ChemAxon
logS-1ALOGPS
pKa (Strongest Acidic)11.33ChemAxon
pKa (Strongest Basic)0.078ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area153.98 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity62.4 m³·mol⁻¹ChemAxon
Polarizability25.52 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC10H12N4O6
IUPAC name9-[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-9H-purine-2,6-diol
InChI IdentifierInChI=1S/C10H12N4O6/c15-1-3-5(16)6(17)9(20-3)14-2-11-4-7(14)12-10(19)13-8(4)18/h2-3,5-6,9,15-17H,1H2,(H2,12,13,18,19)
InChI KeyUBORTCNDUKBEOP-UHFFFAOYSA-N
Isomeric SMILESOCC1OC(C(O)C1O)N1C=NC2=C1N=C(O)N=C2O
Average Molecular Weight284.2255
Monoisotopic Molecular Weight284.075684136
Classification
Description Belongs to the class of organic compounds known as purine nucleosides. Purine nucleosides are compounds comprising a purine base attached to a ribosyl or deoxyribosyl moiety.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPurine nucleosides
Sub ClassNot Available
Direct ParentPurine nucleosides
Alternative Parents
Substituents
  • Purine nucleoside
  • Glycosyl compound
  • N-glycosyl compound
  • Xanthine
  • 6-oxopurine
  • Purinone
  • Pentose monosaccharide
  • Purine
  • Imidazopyrimidine
  • Alkaloid or derivatives
  • Pyrimidone
  • Pyrimidine
  • Monosaccharide
  • N-substituted imidazole
  • Imidazole
  • Heteroaromatic compound
  • Tetrahydrofuran
  • Azole
  • Vinylogous amide
  • Lactam
  • Urea
  • Secondary alcohol
  • Organoheterocyclic compound
  • Azacycle
  • Oxacycle
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Alcohol
  • Primary alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
Charge0
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0940000000-68452b15ecf92f55bc31Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0900000000-ae801ed00992f79b70daSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f79-2900000000-c426dbd88b86eaab5916Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0f8c-1590000000-280418101f13bd239fe6Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0f6x-6910000000-263ac1943def8fa46bc3Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9800000000-263ab0fee77b0b93930cSpectrum
NMRNot Available
ChemSpider ID58484
ChEMBL IDCHEMBL402439
KEGG Compound IDC01762
Pubchem Compound ID64959
Pubchem Substance IDNot Available
ChEBI ID18107
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB00299
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID38352
KNApSAcK IDC00007222
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
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.