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Record Information
Version	2.0
Creation Date	2012-05-31 13:54:28 -0600
Update Date	2015-06-03 15:54:12 -0600
Secondary Accession Numbers	ECMDB01554
Identification
Name:	Xanthylic acid
Description	Xanthylic acid is an important metabolic intermediate in the purine metabolism, and is a product or substrate of the enzymes inosine monophosphate dehydrogenase (EC 1.1.1.205), hypoxanthine phosphoribosyltransferase (EC 2.4.2.8), xanthine phosphoribosyltransferase (EC 2.4.2.22), 5'-ribonucleotide phosphohydrolase (EC 3.1.3.5), Ap4A hydrolase (EC 3.6.1.17), nucleoside-triphosphate diphosphatase (EC 3.6.1.19), phosphoribosylamine-glycine ligase (EC 6.3.4.1), and glutamine amidotransferase (EC 6.3.5.2). (KEGG)
Structure	MOLSDFPDBSMILESInChI × Structure for #<Compound:0xa20d6c20> Close
Synonyms:	(9-D-ribosylxanthine)-5'-phosphate (9-D-Ribosylxanthine)-5'-phosphoric acid 5'-Xanthonylate monophosphate 5'-Xanthonylic acid monophosphate 5'-Xanthonylic acid monophosphoric acid 9-(5-phospho-β-D-ribosyl)xanthine 9-(5-phospho-b-D-Ribosyl)xanthine 9-(5-Phospho-beta-D-ribosyl)xanthine 9-(5-phospho-β-D-Ribosyl)xanthine Xanthosine 5'-phosphate Xanthosine 5'-phosphoric acid Xanthosine-5'-P Xanthosine-5'-phosphate Xanthosine-5'-phosphoric acid Xanthosine-5-P Xanthosine-5-phosphate Xanthosine-5-phosphoric acid Xanthylate XMP
Chemical Formula:	C10H13N4O9P
Weight:	Average: 364.2054 Monoisotopic: 364.042014546
InChI Key:	DCTLYFZHFGENCW-UUOKFMHZSA-N
InChI:	InChI=1S/C10H13N4O9P/c15-5-3(1-22-24(19,20)21)23-9(6(5)16)14-2-11-4-7(14)12-10(18)13-8(4)17/h2-3,5-6,9,15-16H,1H2,(H2,19,20,21)(H2,12,13,17,18)/t3-,5-,6-,9-/m1/s1
CAS number:	523-98-8
IUPAC Name:	{[(2R,3S,4R,5R)-5-(2,6-dioxo-2,3,6,9-tetrahydro-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid
Traditional IUPAC Name:	xanthosine monophosphate
SMILES:	O[C@@H]1[C@@H](COP(O)(O)=O)O[C@H]([C@@H]1O)N1C=NC2=C1NC(=O)NC2=O
Chemical Taxonomy
Description	belongs to the class of organic compounds known as purine ribonucleoside monophosphates. These are nucleotides consisting of a purine base linked to a ribose to which one monophosphate group is attached.
Kingdom	Organic compounds
Super Class	Nucleosides, nucleotides, and analogues
Class	Purine nucleotides
Sub Class	Purine ribonucleotides
Direct Parent	Purine ribonucleoside monophosphates
Alternative Parents	Pentose phosphates Xanthines Glycosylamines 6-oxopurines Monosaccharide phosphates Alkaloids and derivatives Monoalkyl phosphates Pyrimidones N-substituted imidazoles Vinylogous amides Tetrahydrofurans Heteroaromatic compounds Secondary alcohols Lactams Ureas 1,2-diols Oxacyclic compounds Azacyclic compounds Hydrocarbon derivatives Organopnictogen compounds Organic oxides Organonitrogen compounds
Substituents	Purine ribonucleoside monophosphate Pentose phosphate Pentose-5-phosphate Glycosyl compound N-glycosyl compound Xanthine 6-oxopurine Monosaccharide phosphate Pentose monosaccharide Purinone Imidazopyrimidine Purine Alkaloid or derivatives Monoalkyl phosphate Pyrimidone Monosaccharide N-substituted imidazole Organic phosphoric acid derivative Alkyl phosphate Phosphoric acid ester Pyrimidine Heteroaromatic compound Azole Vinylogous amide Imidazole Tetrahydrofuran Lactam 1,2-diol Urea Secondary alcohol Azacycle Oxacycle Organoheterocyclic compound Alcohol Organic oxide Organonitrogen compound Organopnictogen compound Organic oxygen compound Organooxygen compound Hydrocarbon derivative Organic nitrogen compound Aromatic heteropolycyclic compound
Molecular Framework	Aromatic heteropolycyclic compounds
External Descriptors	xanthosine 5'-phosphate (CHEBI:15652 ) purine ribonucleoside 5'-monophosphate (CHEBI:15652 ) Purine alkaloids (C00655 )
Physical Properties
State:	Solid
Charge:	-2
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 2.49 g/L ALOGPS logP -1.9 ALOGPS logP -2.2 ChemAxon logS -2.2 ALOGPS pKa (Strongest Acidic) 1.26 ChemAxon pKa (Strongest Basic) 0.069 ChemAxon Physiological Charge -2 ChemAxon Hydrogen Acceptor Count 9 ChemAxon Hydrogen Donor Count 6 ChemAxon Polar Surface Area 192.47 Ų ChemAxon Rotatable Bond Count 4 ChemAxon Refractivity 73.08 m³·mol⁻¹ ChemAxon Polarizability 29.99 ų ChemAxon Number of Rings 3 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule Yes ChemAxon
Biological Properties
Cellular Locations:	Cytoplasm
Reactions:	Water + Xanthylic acid > Phosphate + Xanthosine Phosphoribosyl pyrophosphate + Xanthine <> Pyrophosphate + Xanthylic acid Adenosine triphosphate + L-Glutamine + Water + Xanthylic acid > Adenosine monophosphate + L-Glutamate + Guanosine monophosphate +2 Hydrogen ion + Pyrophosphate Water + Inosinic acid + NAD <> Hydrogen ion + NADH + Xanthylic acid Water + Xanthosine 5-triphosphate > Hydrogen ion + Pyrophosphate + Xanthylic acid Adenosine triphosphate + Xanthylic acid + Ammonia <> Adenosine monophosphate + Pyrophosphate + Guanosine monophosphate Adenosine triphosphate + Xanthylic acid + L-Glutamine + Water <> Adenosine monophosphate + Pyrophosphate + Guanosine monophosphate + L-Glutamate Xanthylic acid + Pyrophosphate <> Xanthine + Phosphoribosyl pyrophosphate Xanthylic acid + Water <> Xanthosine + Phosphate Xanthosine 5-triphosphate + Water <> Xanthylic acid + Pyrophosphate Water + L-Glutamine + Xanthylic acid + Adenosine triphosphate > Hydrogen ion + L-Glutamate + Guanosine monophosphate + Pyrophosphate + Adenosine monophosphate Adenosine triphosphate + Xanthylic acid + Ammonia > Hydrogen ion + Adenosine monophosphate + Pyrophosphate + Guanosine monophosphate Water + NAD + Inosinic acid > Hydrogen ion + NADH + Xanthylic acid Xanthylic acid + Pyrophosphate < Xanthine + Phosphoribosyl pyrophosphate Adenosine triphosphate + Xanthylic acid + L-Glutamine + Water > Adenosine monophosphate + Pyrophosphate + Guanosine monophosphate + L-Glutamate Inosinic acid + NAD + Water > Xanthylic acid + NADH Xanthylic acid + Pyrophosphate > Phosphoribosyl pyrophosphate + Xanthine Xanthosine 5-triphosphate + Water + 2'-Deoxyinosine triphosphate <> Xanthylic acid + Pyrophosphate + DIMP Adenosine triphosphate + Xanthylic acid + L-Glutamine + Water + Ammonia <> Adenosine monophosphate + Pyrophosphate + Guanosine monophosphate + L-Glutamate Xanthylic acid + Adenosine triphosphate + L-Glutamine + Water > Adenosine monophosphate + Pyrophosphate + L-Glutamic acid +2 Hydrogen ion + Guanosine monophosphate + L-Glutamate Xanthine + Phosphoribosyl pyrophosphate > Xanthylic acid + Pyrophosphate Adenosine triphosphate + L-Glutamine + Water + Xanthylic acid > Adenosine monophosphate + L-Glutamate + Guanosine monophosphate +2 Hydrogen ion + Pyrophosphate Water + Inosinic acid + NAD <> Hydrogen ion + NADH + Xanthylic acid Adenosine triphosphate + L-Glutamine + Water + Xanthylic acid > Adenosine monophosphate + L-Glutamate + Guanosine monophosphate +2 Hydrogen ion + Pyrophosphate Water + Inosinic acid + NAD <> Hydrogen ion + NADH + Xanthylic acid
SMPDB Pathways:	purine nucleotides de novo biosynthesis PW000910 purine nucleotides de novo biosynthesis 1435709748 PW000960 purine nucleotides de novo biosynthesis 2 PW002033 purine ribonucleosides degradation PW002076
KEGG Pathways:	Drug metabolism - other enzymes ec00983 Metabolic pathways eco01100 Purine metabolism ec00230 Thiamine metabolism ec00730
EcoCyc Pathways:	guanosine nucleotides de novo biosynthesis PWY-6125 xanthine and xanthosine salvage SALVPURINE2-PWY
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive splash10-0002-9613000000-3054f73e4c9456039ed6 View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive splash10-01ot-9521200000-1e6fc3c628d8ebd23b37 View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive Not Available View in JSpectraViewer LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QTOF , negative splash10-0ik9-7964000000-bce7ee60221f82790f35 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QTOF , positive splash10-0002-9400000000-05c1ae772c001a15a8c6 View in MoNA LC-MS/MS LC-MS/MS Spectrum - 35V, Positive splash10-0002-9200000000-743d2f19ea30c814c56a View in MoNA LC-MS/MS LC-MS/MS Spectrum - 10V, Positive splash10-0002-9210000000-f36c079a2869c6c7c63d View in MoNA LC-MS/MS LC-MS/MS Spectrum - 20V, Positive splash10-0002-9300000000-0cea344051256ed9d642 View in MoNA LC-MS/MS LC-MS/MS Spectrum - 40V, Positive splash10-0002-9300000000-1295bb6a6dfffef31dd2 View in MoNA LC-MS/MS LC-MS/MS Spectrum - 20V, Positive splash10-0002-9400000000-7125a3a52d3308d6b367 View in MoNA LC-MS/MS LC-MS/MS Spectrum - 40V, Negative splash10-0fb9-9400000000-f93509061523b8f0b012 View in MoNA LC-MS/MS LC-MS/MS Spectrum - 10V, Positive splash10-0002-9310000000-a910c200bfc66c8e1c46 View in MoNA LC-MS/MS LC-MS/MS Spectrum - 40V, Positive splash10-0002-9000000000-1ff54bb8d71e1ea585f2 View in MoNA LC-MS/MS LC-MS/MS Spectrum - 20V, Negative splash10-03fs-9380000000-2a0fbd1929733b4918d1 View in MoNA LC-MS/MS LC-MS/MS Spectrum - 10V, Negative splash10-03di-1039000000-f0bd4ff644ac79937301 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-0udi-0913000000-d17f1d77b992fc6e9f04 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-0udi-0900000000-efbdb918f50ba610575d View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-0udi-2900000000-cf070bd16aacd3dcb6fb View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-0imi-6509000000-d931cb1dcaeba678220c View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-0fbc-9300000000-e596281ec38113a9653c View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-004i-9100000000-1caa46ecd17db343ddd3 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-0udi-0900000000-ac450658003af6c0a109 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-0udi-0900000000-448bfe6677d2f8fe1f3c View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-0udi-1900000000-10c12403e596a9b5bf0a View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-03di-3009000000-8a668987618bcd1531e7 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-004i-9000000000-4b2bf772bc8415c9f24c View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-004i-9201000000-907dd40cbb70b7a5c62d View in MoNA 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer
References
References:	Albrecht W, Storck M, Pfetsch E, Martin W, Abendroth D: Development and application of a high-performance liquid chromatography-based assay for determination of the activity of inosine 5'-monophosphate dehydrogenase in whole blood and isolated mononuclear cells. Ther Drug Monit. 2000 Jun;22(3):283-94. Pubmed: 10850395 Barsotti C, Pesi R, Giannecchini M, Ipata PL: Evidence for the involvement of cytosolic 5'-nucleotidase (cN-II) in the synthesis of guanine nucleotides from xanthosine. J Biol Chem. 2005 Apr 8;280(14):13465-9. Epub 2005 Feb 6. Pubmed: 15699053 Daxecker H, Raab M, Muller MM: Influence of mycophenolic acid on inosine 5'-monophosphate dehydrogenase activity in human peripheral blood mononuclear cells. Clin Chim Acta. 2002 Apr;318(1-2):71-7. Pubmed: 11880114 Digits JA, Hedstrom L: Drug selectivity is determined by coupling across the NAD+ site of IMP dehydrogenase. Biochemistry. 2000 Feb 22;39(7):1771-7. Pubmed: 10677226 Digits JA, Hedstrom L: Species-specific inhibition of inosine 5'-monophosphate dehydrogenase by mycophenolic acid. Biochemistry. 1999 Nov 16;38(46):15388-97. Pubmed: 10563825 Franchetti P, Grifantini M: Nucleoside and non-nucleoside IMP dehydrogenase inhibitors as antitumor and antiviral agents. Curr Med Chem. 1999 Jul;6(7):599-614. Pubmed: 10390603 Frueh FW, Hayashibara KC, Brown PO, Whitlock JP Jr: Use of cDNA microarrays to analyze dioxin-induced changes in human liver gene expression. Toxicol Lett. 2001 Jul 6;122(3):189-203. Pubmed: 11489354 Glander P, Braun KP, Hambach P, Bauer S, Mai I, Roots I, Waiser J, Fritsche L, Neumayer HH, Budde K: Non-radioactive determination of inosine 5'-monophosphate dehydro-genase (IMPDH) in peripheral mononuclear cells. Clin Biochem. 2001 Oct;34(7):543-9. Pubmed: 11738390 Hedstrom L: IMP dehydrogenase: mechanism of action and inhibition. Curr Med Chem. 1999 Jul;6(7):545-60. Pubmed: 10390600 Heroux A, White EL, Ross LJ, Borhani DW: Crystal structures of the Toxoplasma gondii hypoxanthine-guanine phosphoribosyltransferase-GMP and -IMP complexes: comparison of purine binding interactions with the XMP complex. Biochemistry. 1999 Nov 2;38(44):14485-94. Pubmed: 10545170 Heroux A, White EL, Ross LJ, Davis RL, Borhani DW: Crystal structure of Toxoplasma gondii hypoxanthine-guanine phosphoribosyltransferase with XMP, pyrophosphate, and two Mg(2+) ions bound: insights into the catalytic mechanism. Biochemistry. 1999 Nov 2;38(44):14495-506. Pubmed: 10545171 Jayaram HN, Cooney DA, Grusch M, Krupitza G: Consequences of IMP dehydrogenase inhibition, and its relationship to cancer and apoptosis. Curr Med Chem. 1999 Jul;6(7):561-74. Pubmed: 10390601 Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510 Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882 Khalil PN, Erb N, Khalil MN, Escherich G, Janka-Schaub GE: Validation and application of a high-performance liquid chromatographic-based assay for determination of the inosine 5'-monophosphate dehydrogenase activity in erythrocytes. J Chromatogr B Analyt Technol Biomed Life Sci. 2006 Sep 14;842(1):1-7. Epub 2006 May 24. Pubmed: 16725387 Markland W, McQuaid TJ, Jain J, Kwong AD: Broad-spectrum antiviral activity of the IMP dehydrogenase inhibitor VX-497: a comparison with ribavirin and demonstration of antiviral additivity with alpha interferon. Antimicrob Agents Chemother. 2000 Apr;44(4):859-66. Pubmed: 10722482 McMillan FM, Cahoon M, White A, Hedstrom L, Petsko GA, Ringe D: Crystal structure at 2.4 A resolution of Borrelia burgdorferi inosine 5'-monophosphate dehydrogenase: evidence of a substrate-induced hinged-lid motion by loop 6. Biochemistry. 2000 Apr 18;39(15):4533-42. Pubmed: 10758003 Minakawa N, Matsuda A: Mechanism-based design of inosine 5-monophosphate dehydrogenase inhibitors: synthesis and biological activities of 5-ethynyl-1-beta-D-ribofuranosylimidazole-4-carboxamide (EICAR) and its derivatives. Curr Med Chem. 1999 Jul;6(7):615-28. Pubmed: 10390604 Pitera JW, Munagala NR, Wang CC, Kollman PA: Understanding substrate specificity in human and parasite phosphoribosyltransferases through calculation and experiment. Biochemistry. 1999 Aug 10;38(32):10298-306. Pubmed: 10441123 Prosise GL, Luecke H: Crystal structures of Tritrichomonasfoetus inosine monophosphate dehydrogenase in complex with substrate, cofactor and analogs: a structural basis for the random-in ordered-out kinetic mechanism. J Mol Biol. 2003 Feb 14;326(2):517-27. Pubmed: 12559919 Rauniyar RK, Suzuma K, King AL, Aiello LP, King GL: Differential effects of bactericidal/permeability-increasing protein (BPI) analogues on retinal neovascularization and retinal pericyte growth. Invest Ophthalmol Vis Sci. 2002 Feb;43(2):503-9. Pubmed: 11818397 Sintchak MD, Nimmesgern E: The structure of inosine 5'-monophosphate dehydrogenase and the design of novel inhibitors. Immunopharmacology. 2000 May;47(2-3):163-84. Pubmed: 10878288 Stoychev G, Kierdaszuk B, Shugar D: Xanthosine and xanthine. Substrate properties with purine nucleoside phosphorylases, and relevance to other enzyme systems. Eur J Biochem. 2002 Aug;269(16):4048-57. Pubmed: 12180982 van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195 Vethe NT, Bergan S: Determination of inosine monophosphate dehydrogenase activity in human CD4+ cells isolated from whole blood during mycophenolic acid therapy. Ther Drug Monit. 2006 Oct;28(5):608-13. Pubmed: 17038874 Wall M, Shim JH, Benkovic SJ: Human AICAR transformylase: role of the 4-carboxamide of AICAR in binding and catalysis. Biochemistry. 2000 Sep 19;39(37):11303-11. Pubmed: 10985775 Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064 Wolan DW, Cheong CG, Greasley SE, Wilson IA: Structural insights into the human and avian IMP cyclohydrolase mechanism via crystal structures with the bound XMP inhibitor. Biochemistry. 2004 Feb 10;43(5):1171-83. Pubmed: 14756553
Synthesis Reference:	Hattori, Kyoji; Kawahara, Shin; Hagiwara, Takeshige. 5'-Xanthylic acid. Jpn. Kokai Tokkyo Koho (1985), 3 pp.
Material Safety Data Sheet (MSDS)	Not Available
Links
External Links:	Resource Link CHEBI ID 15652 HMDB ID HMDB01554 Pubchem Compound ID 1190 Kegg ID C00655 ChemSpider ID 66054 Wikipedia XMP BioCyc ID XANTHOSINE-5-PHOSPHATE EcoCyc ID XANTHOSINE-5-PHOSPHATE Ligand Expo XMP

Enzymes

Transporters