1.0 2011-09-21 00:05:26 UTC 2015-07-21 06:56:53 UTC FDB021932 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. XTP competitively inhibits the binding of GTP to the guanine nucleotide-binding site of retinal G-protein, transducin (TD). These suggests that GTP, ITP, and XTP are differential signal sorters and signal amplifiers at the G-protein level. G-proteins mediate signal transfer from receptors to effector systems. (PMID: 9337071) 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). (KEGG) [HMDB] 5'-XTP O(5')-(Tetrahydroxytrioryl)xanthosine Triphopsphate 1-xanthosin-5'-yl ester Triphopsphic acid 1-xanthosin-5'-yl ester Triphopsphoric acid 1-xanthosin-5'-yl ester Xanthosine 5'-triate Xanthosine 5'-triic acid Xanthosine 5'-triphosphate Xanthosine 5'-triphosphic acid Xanthosine mono(tetrahydrogen triate) Xanthosine mono(tetrahydrogen triphosphate) Xanthosine triate Xanthosine triic acid Xanthosine triphosphate 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 belongs to the class of organic compounds known as purine ribonucleoside triphosphates. These are purine ribobucleotides with a triphosphate group linked to the ribose moiety. Purine ribonucleoside triphosphates Organic compounds Nucleosides, nucleotides, and analogues Purine nucleotides Purine ribonucleotides Aromatic heteropolycyclic compounds 1,2-diols Alkaloids and derivatives Azacyclic compounds Glycosylamines Heteroaromatic compounds Hydrocarbon derivatives Hydroxypyrimidines Monoalkyl phosphates Monosaccharide phosphates N-substituted imidazoles Organic oxides Organonitrogen compounds Organopnictogen compounds Oxacyclic compounds Pentose phosphates Purine ribonucleoside monophosphates Secondary alcohols Tetrahydrofurans Xanthines 1,2-diol Alcohol Alkaloid or derivatives Alkyl phosphate Aromatic heteropolycyclic compound Azacycle Azole Glycosyl compound Heteroaromatic compound Hydrocarbon derivative Hydroxypyrimidine Imidazole Imidazopyrimidine Monoalkyl phosphate Monosaccharide Monosaccharide phosphate N-glycosyl compound N-substituted imidazole Organic nitrogen compound Organic oxide Organic oxygen compound Organic phosphoric acid derivative Organoheterocyclic compound Organonitrogen compound Organooxygen compound Organopnictogen compound Oxacycle Pentose monosaccharide Pentose phosphate Pentose-5-phosphate Phosphoric acid ester Purine Purine ribonucleoside monophosphate Purine ribonucleoside triphosphate Pyrimidine Secondary alcohol Tetrahydrofuran Xanthine purine ribonucleoside 5'-triphosphate xanthosine 5'-phosphate Solid 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 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::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::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 #<Reference:0x000055ce32e3eff8> #<Reference:0x000055ce32e3ee40> Anatidae Type 1 specific Anatidae 8830 Beefalo Type 1 specific Bos taurus X Bison bison 297284 Bison Type 1 specific Bison bison 9901 Buffalo Type 1 specific Bubalus bubalis 89462 Cattle (Beef, Veal) Type 1 specific Bos taurus 9913 Chicken Type 1 specific Gallus gallus 9031 Columbidae (Dove, Pigeon) Type 1 specific Columbidae 8930 Deer Type 1 specific Cervidae 9850 Domestic goat Type 1 specific Capra aegagrus hircus 9925 Domestic pig Type 1 specific Sus scrofa domestica 9825 Elk Type 1 specific Cervus canadensis 1574408 Emu Type 1 specific Dromaius novaehollandiae 8790 European rabbit Type 1 specific Oryctolagus 9984 Greylag goose Type 1 specific Anser anser 8843 Guinea hen Type 1 specific Numida meleagris 8996 Horse Type 1 specific Equus caballus 9796 Mallard duck Type 1 specific Anas platyrhynchos 8839 Mountain hare Type 1 specific Lepus timidus 62621 Mule deer Type 1 specific Odocoileus 9871 Ostrich Type 1 specific Struthio camelus 8801 Pheasant Type 1 specific Phasianus colchicus 9054 Quail Type 1 specific Phasianidae 9005 Rabbit Type 1 specific Leporidae 9979 Rock ptarmigan Type 1 specific Lagopus muta 64668 Sheep (Mutton, Lamb) Type 1 specific Ovis aries 9940 Squab Type 1 specific Columba 8931 Turkey Type 1 specific Meleagris gallopavo 9103 Velvet duck Type 1 specific Melanitta fusca 371864 Wild boar Type 1 specific Sus scrofa 9823