2.0 2012-05-31 10:25:49 -0600 2015-06-03 15:53:27 -0600 ECMDB00293 M2MDB000122 Xanthosine 5-triphosphate Xanthosine 5-triphosphate (XTP) is a Guanosine triphosphate (GTP) analogue. The base of XTP, xanthine, bears a keto group instead of an amino group at C2 of the purine rings. XTP can substitute for GTP in supporting receptor-mediated adenylyl cyclase activation. Xanthosine 5-triphosphate is an intermediate of the Purine metabolism pathway, a substrate of the enzymes dinucleoside tetraphosphatase (EC 3.6.1.17) and nucleoside-triphosphate pyrophosphatase (EC 3.6.1.19). It is also a substrate for Xanthine triphosphatase, which is a phosphatase that hydrolyzes non-canonical purine nucleotides such as XTP and ITP to their respective diphosphate derivatives. 5'-XTP Xanthosine 5'-triphosphate Xanthosine 5'-triphosphoric acid Xanthosine 5-triphosphoric acid Xanthosine mono(tetrahydrogen triphosphate) Xanthosine mono(tetrahydrogen triphosphoric acid) Xanthosine triphosphate Xanthosine triphosphoric acid XTP C10H15N4O15P3 524.1652 523.974675366 ({[({[(2R,3S,4R,5R)-5-(2,6-dihydroxy-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphonic acid xanthosine 5-triphosphate 6253-56-1 O[C@@H]1[C@@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)O[C@H]([C@@H]1O)N1C=NC2=C1N=C(O)N=C2O InChI=1S/C10H15N4O15P3/c15-5-3(1-26-31(22,23)29-32(24,25)28-30(19,20)21)27-9(6(5)16)14-2-11-4-7(14)12-10(18)13-8(4)17/h2-3,5-6,9,15-16H,1H2,(H,22,23)(H,24,25)(H2,19,20,21)(H2,12,13,17,18)/t3-,5-,6-,9-/m1/s1 CAEFEWVYEZABLA-UUOKFMHZSA-N Solid Cytosol logp -0.45 ALOGPS logs -2.11 ALOGPS solubility 4.04e+00 g/l ALOGPS logp -4.1 ChemAxon pka_strongest_acidic 0.96 ChemAxon pka_strongest_basic 0.016 ChemAxon iupac ({[({[(2R,3S,4R,5R)-5-(2,6-dihydroxy-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphonic acid ChemAxon average_mass 524.1652 ChemAxon mono_mass 523.974675366 ChemAxon smiles O[C@@H]1[C@@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)O[C@H]([C@@H]1O)N1C=NC2=C1N=C(O)N=C2O ChemAxon formula C10H15N4O15P3 ChemAxon inchi InChI=1S/C10H15N4O15P3/c15-5-3(1-26-31(22,23)29-32(24,25)28-30(19,20)21)27-9(6(5)16)14-2-11-4-7(14)12-10(18)13-8(4)17/h2-3,5-6,9,15-16H,1H2,(H,22,23)(H,24,25)(H2,19,20,21)(H2,12,13,17,18)/t3-,5-,6-,9-/m1/s1 ChemAxon inchikey CAEFEWVYEZABLA-UUOKFMHZSA-N ChemAxon polar_surface_area 293.57 ChemAxon refractivity 95.02 ChemAxon polarizability 39.11 ChemAxon rotatable_bond_count 8 ChemAxon acceptor_count 15 ChemAxon donor_count 8 ChemAxon physiological_charge -3 ChemAxon formal_charge 0 ChemAxon Purine metabolism ec00230 Thiamine metabolism ec00730 Collection of Reactions without pathways PW001891 Metabolic Specdb::CMs 15558 Specdb::CMs 37407 Specdb::CMs 1056912 Specdb::CMs 1056913 Specdb::CMs 1056915 Specdb::CMs 1056917 Specdb::CMs 1056919 Specdb::CMs 1056921 Specdb::CMs 1056923 Specdb::CMs 1056925 Specdb::CMs 1056926 Specdb::CMs 1056929 Specdb::CMs 1056931 Specdb::CMs 1056933 Specdb::CMs 1056935 Specdb::CMs 1056937 Specdb::CMs 1056939 Specdb::CMs 1056941 Specdb::CMs 1056943 Specdb::CMs 1056944 Specdb::CMs 1056945 Specdb::CMs 1056947 Specdb::CMs 1056949 Specdb::CMs 1056951 Specdb::CMs 1056953 Specdb::NmrOneD 143370 Specdb::NmrOneD 143371 Specdb::NmrOneD 143372 Specdb::NmrOneD 143373 Specdb::NmrOneD 143374 Specdb::NmrOneD 143375 Specdb::NmrOneD 143376 Specdb::NmrOneD 143377 Specdb::NmrOneD 143378 Specdb::NmrOneD 143379 Specdb::NmrOneD 143380 Specdb::NmrOneD 143381 Specdb::NmrOneD 143382 Specdb::NmrOneD 143383 Specdb::NmrOneD 143384 Specdb::NmrOneD 143385 Specdb::NmrOneD 143386 Specdb::NmrOneD 143387 Specdb::NmrOneD 143388 Specdb::NmrOneD 143389 Specdb::MsMs 27920 Specdb::MsMs 27921 Specdb::MsMs 27922 Specdb::MsMs 34478 Specdb::MsMs 34479 Specdb::MsMs 34480 Specdb::MsMs 2758455 Specdb::MsMs 2758456 Specdb::MsMs 2758457 Specdb::MsMs 2950332 Specdb::MsMs 2950333 Specdb::MsMs 2950334 HMDB00293 121887 388429 C00700 XTP XTP 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. 21097882 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. 22080510 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. 17765195 Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. 19212411 Klinker JF, Seifert R: Functionally nonequivalent interactions of guanosine 5'-triphosphate, inosine 5'-triphosphate, and xanthosine 5'-triphosphate with the retinal G-protein, transducin, and with Gi-proteins in HL-60 leukemia cell membranes. Biochem Pharmacol. 1997 Sep 1;54(5):551-62. 9337071 anachkov I; Pan J Y; Wessling-Resnick M; Wright G E Synthesis and effect of nonhydrolyzable xanthosine triphosphate derivatives on prenylation of Rab5D136N. Molecular pharmacology (1997), 51(1), 47-51. Nucleoside-triphosphatase rdgB P52061 RDGB_ECOLI rdgB http://ecmdb.ca/proteins/P52061.xml UPF0244 protein yjjX P39411 YJJX_ECOLI yjjX http://ecmdb.ca/proteins/P39411.xml Water + Xanthosine 5-triphosphate > Hydrogen ion + Pyrophosphate + Xanthylic acid R02720 RXN0-1603 Water + Xanthosine 5-triphosphate > Hydrogen ion + Phosphate + XDP RXN0-5074 Guanosine triphosphate + Hydrogen ion + Water > Ammonium + Xanthosine 5-triphosphate Xanthosine 5-triphosphate + Water <> Xanthylic acid + Pyrophosphate R02720 Xanthosine 5-triphosphate + Water + 2'-Deoxyinosine triphosphate <> Xanthylic acid + Pyrophosphate + DIMP R02720