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Identification
YMDB IDYMDB00263
NameXanthine
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionXanthine, also known as Xan or 2,6-dioxopurine, belongs to the class of organic compounds known as xanthines. These are purine derivatives with a ketone group conjugated at carbons 2 and 6 of the purine moiety. Xanthine is an extremely weak basic (essentially neutral) compound (based on its pKa). Xanthine exists in all living species, ranging from bacteria to humans. Xanthine is a potentially toxic compound.
Structure
Thumb
Synonyms
  • 1H-Purine-2, 6-diol
  • 1H-Purine-2,6-diol
  • 1H-Purine-2,6-dione, 3,7-dihydro-
  • 2,6-Dihydroxypurine
  • 2,6-Dioxo-1,2,3, 6-tetrahydropurine
  • 2,6-Dioxo-1,2,3,6-tetrahydropurine
  • 2,6-Dioxopurine
  • 2,6(1,3)-Purinedion
  • 3,7-Dihydro-1H-purine-2,6-dione
  • 3,7-dihydropurine-2,6-dione
  • 9H-purine-2,6-(1H,3H)-dione
  • 9H-Purine-2,6-diol
  • 9H-Purine-2,6(1H,3H)-dione
  • Dioxopurine
  • Isoxanthine
  • Pseudoxanthine
  • Purine-2,6-diol
  • Purine-2,6(1H,3H)-dione
  • purine-2(3H),6(1H)-dione
  • Xan
  • Xanthic oxide
  • Xanthin
  • Xanthine
  • Xanthine (VAN)
CAS number69-89-6
WeightAverage: 152.1109
Monoisotopic: 152.033425392
InChI KeyLRFVTYWOQMYALW-UHFFFAOYSA-N
InChIInChI=1S/C5H4N4O2/c10-4-2-3(7-1-6-2)8-5(11)9-4/h1H,(H3,6,7,8,9,10,11)
IUPAC Name2,3,6,7-tetrahydro-1H-purine-2,6-dione
Traditional IUPAC Namexanthine
Chemical FormulaC5H4N4O2
SMILES[H]N1C([H])=NC2=C1C(=O)N([H])C(=O)N2[H]
Chemical Taxonomy
Description belongs to the class of organic compounds known as xanthines. These are purine derivatives with a ketone group conjugated at carbons 2 and 6 of the purine moiety.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassImidazopyrimidines
Sub ClassPurines and purine derivatives
Direct ParentXanthines
Alternative Parents
Substituents
  • Xanthine
  • 6-oxopurine
  • Purinone
  • Alkaloid or derivatives
  • Pyrimidone
  • Pyrimidine
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Vinylogous amide
  • Lactam
  • Urea
  • Azacycle
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting point>300 °C
Experimental Properties
PropertyValueReference
Water Solubility0.069 mg/mL at 16 oC [MERCK INDEX (1996)]PhysProp
LogP-0.73 [HANSCH,C ET AL. (1995)]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility4.91 g/LALOGPS
logP-0.65ALOGPS
logP-0.21ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)7.95ChemAxon
pKa (Strongest Basic)-0.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area86.88 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity36.92 m³·mol⁻¹ChemAxon
Polarizability12.7 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • extracellular
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB PathwaysNot Available
KEGG Pathways
Purine metabolismec00230 Map00230
SMPDB ReactionsNot Available
KEGG Reactions
water + hydron + GuanineXanthine + Ammonium
phosphate + xanthosineXanthine + Ribose 1-phosphate
Xanthine + Phosphoribosyl pyrophosphatePyrophosphate + Xanthylic acid
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0f6t-0924000000-9b80e0a2a60c73ca0180JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0f6t-0924000000-9b80e0a2a60c73ca0180JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0f6t-0924000000-30dc5892eecde860846aJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0kai-7900000000-2dc30b0fc4cff2239dbeJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0udi-0900000000-a70539989d121bfacee0JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0a4i-6900000000-b047b06406308dbaeda8JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0a4i-9300000000-ed480ed920c3e9b576ecJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0zfr-0900000000-efb049914c9bce596267JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0zfr-0900000000-efb049914c9bce596267JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-0udi-0900000000-5fee91293851bb02193eJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , positivesplash10-000i-0900000000-4568a814903ff411923aJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000000-2e9e069e2df414aed037JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0w29-0900000000-fa52193346bc456d89e8JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a5i-9400000000-bbf70998e8b7515cb440JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-566d663553ce4f0ec207JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0zfr-1900000000-d0a5d2c0f89f8d42d903JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-351d9f8ee3470f911829JSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-0udi-7900000000-2d5ab5d5db8ff4981467JSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • Saint-Marc, C., Daignan-Fornier, B. (2004). "GUD1 (YDL238c) encodes Saccharomyces cerevisiae guanine deaminase, an enzyme expressed during post-diauxic growth." Yeast 21:1359-1363.15565584
Synthesis Reference:Procedure for the production of xanthine and xanthine-like materials. Fr. (1967), 4 pp.
External Links:
ResourceLink
CHEBI ID48517
HMDB IDHMDB00292
Pubchem Compound ID1188
Kegg IDC00385
ChemSpider ID1151
FOODB IDFDB001977
WikipediaXanthine
BioCyc IDXANTHINE

Enzymes

General function:
Involved in purine-nucleoside phosphorylase activity
Specific function:
Cleavage of guanosine or inosine to respective bases and sugar-1-phosphate molecules
Gene Name:
PNP1
Uniprot ID:
Q05788
Molecular weight:
33754.60156
Reactions
Purine nucleoside + phosphate → purine + alpha-D-ribose 1-phosphate.
General function:
Involved in hydrolase activity
Specific function:
Catalyzes the hydrolytic deamination of guanine, producing xanthine and ammonia
Gene Name:
GUD1
Uniprot ID:
Q07729
Molecular weight:
55203.19922
Reactions
Guanine + H(2)O → xanthine + NH(3).
General function:
Involved in nucleoside metabolic process
Specific function:
May act as a xanthine phosphoribosyltransferase involved in the synthesis of purine nucleotides. Such activity is however unclear in vivo
Gene Name:
XPT1
Uniprot ID:
P47165
Molecular weight:
23671.0
Reactions