2.0 2012-05-31 13:54:28 -0600 2015-06-03 15:54:12 -0600 ECMDB01554 M2MDB000419 Xanthylic acid 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) (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-&beta;-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 C10H13N4O9P 364.2054 364.042014546 {[(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 xanthosine monophosphate 523-98-8 O[C@@H]1[C@@H](COP(O)(O)=O)O[C@H]([C@@H]1O)N1C=NC2=C1NC(=O)NC2=O 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 DCTLYFZHFGENCW-UUOKFMHZSA-N Solid Cytosol Extra-organism Periplasm logp -1.95 ALOGPS logs -2.17 ALOGPS solubility 2.49e+00 g/l ALOGPS logp -2.2 ChemAxon pka_strongest_acidic 1.26 ChemAxon pka_strongest_basic 0.069 ChemAxon iupac {[(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 ChemAxon average_mass 364.2054 ChemAxon mono_mass 364.042014546 ChemAxon smiles O[C@@H]1[C@@H](COP(O)(O)=O)O[C@H]([C@@H]1O)N1C=NC2=C1NC(=O)NC2=O ChemAxon formula C10H13N4O9P ChemAxon 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 ChemAxon inchikey DCTLYFZHFGENCW-UUOKFMHZSA-N ChemAxon polar_surface_area 192.47 ChemAxon refractivity 73.08 ChemAxon polarizability 29.99 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 9 ChemAxon donor_count 6 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon Purine metabolism ec00230 Drug metabolism - other enzymes ec00983 Thiamine metabolism ec00730 Metabolic pathways eco01100 purine nucleotides de novo biosynthesis The biosynthesis of purine nucleotides is a complex process that begins with a phosphoribosyl pyrophosphate. This compound interacts with water and L-glutamine through a amidophosphoribosyl transferase resulting in a pyrophosphate, L-glutamic acid and a 5-phosphoribosylamine. The latter compound proceeds to interact with a glycine through an ATP driven phosphoribosylamine-glycine ligase resulting in the addition of glycine to the compound. This reaction releases an ADP, a phosphate, a hydrogen ion and a N1-(5-phospho-β-D-ribosyl)glycinamide. The latter compound interacts with formic acid, through an ATP driven phosphoribosylglycinamide formyltransferase 2 resulting in a phosphate, an ADP, a hydrogen ion and a 5-phosphoribosyl-N-formylglycinamide. The latter compound interacts with L-glutamine, and water through an ATP-driven phosphoribosylformylglycinamide synthetase resulting in a release of a phosphate, an ADP, a hydrogen ion, a L-glutamic acid and a 2-(formamido)-N1-(5-phospho-D-ribosyl)acetamidine. The latter compound interacts with an ATP driven phosphoribosylformylglycinamide cyclo-ligase resulting in a release of ADP, a phosphate, a hydrogen ion and a 5-aminoimidazole ribonucleotide. The latter compound interacts with a hydrogen carbonate through an ATP driven N5-carboxyaminoimidazole ribonucleotide synthetase resulting in a release of a phosphate, an ADP, a hydrogen ion and a N5-carboxyaminoimidazole ribonucleotide.The latter compound then interacts with a N5-carboxyaminoimidazole ribonucleotide mutase resulting in a 5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylate. This compound interacts with an L-aspartic acid through an ATP driven phosphoribosylaminoimidazole-succinocarboxamide synthase resulting in a phosphate, an ADP, a hydrogen ion and a SAICAR. SAICAR interacts with an adenylosuccinate lyase resulting in a fumaric acid and an AICAR. AICAR interacts with a formyltetrahydrofolate through a AICAR transformylase / IMP cyclohydrolase resulting in a release of a tetrahydropterol mono-l-glutamate and a FAICAR. The latter compound, FAICAR, interacts in a reversible reaction through a AICAR transformylase / IMP cyclohydrolase resulting in a release of water and Inosinic acid. Inosinic acid can be metabolized to produce dGTP and dATP three different methods each. dGTP: Inosinic acid, water and NAD are processed by IMP dehydrogenase resulting in a release of NADH, a hydrogen ion and Xanthylic acid. Xanthylic acid interacts with L-glutamine, and water through an ATP driven GMP synthetase resulting in pyrophosphate, AMP, L-glutamic acid, a hydrogen ion and Guanosine monophosphate. The latter compound is the phosphorylated by reacting with an ATP driven guanylate kinase resulting in a release of ADP and a Gaunosine diphosphate. Guanosine diphosphate can be metabolized in three different ways: 1.-Guanosine diphosphate is phosphorylated by an ATP-driven nucleoside diphosphate kinase resulting in an ADP and a Guanosine triphosphate. This compound interacts with a reduced flavodoxin protein through a ribonucleoside-triphosphate reductase resulting in a oxidized flavodoxin a water moleculer and a dGTP 2.-Guanosine diphosphate interacts with a reduced NrdH glutaredoxin-like proteins through a ribonucleoside-diphosphate reductase 2 resulting in the release of an oxidized NrdH glutaredoxin-like protein, a water molecule and a dGDP. The dGDP is then phosphorylated by interacting with an ATP-driven nucleoside diphosphate kinase resulting in an ADP and dGTP. 3.-Guanosine diphosphate interacts with a reduced thioredoxin ribonucleoside diphosphate reductase 1 resulting in a release of a water molecule, an oxidized thioredoxin and a dGDP. The dGDP is then phosphorylated by interacting with an ATP-driven nucleoside diphosphate kinase resulting in an ADP and dGTP. dATP: Inosinic acid interacts with L-aspartic acid through an GTP driven adenylosuccinate synthase results in the release of GDP, a hydrogen ion, a phosphate and N(6)-(1,2-dicarboxyethyl)AMP. The latter compound is then cleaved by a adenylosuccinate lyase resulting in a fumaric acid and an Adenosine monophosphate. This compound is then phosphorylated by an adenylate kinase resulting in the release of ATP and an adenosine diphosphate. Adenosine diphosphate can be metabolized in three different ways: 1.-Adenosine diphosphate is involved in a reversible reaction by interacting with a hydrogen ion and a phosphate through a ATP synthase / thiamin triphosphate synthase resulting in a hydrogen ion, a water molecule and an Adenosine triphosphate. The adenosine triphosphate interacts with a reduced flavodoxin through a ribonucleoside-triphosphate reductase resulting in an oxidized flavodoxin, a water molecule and a dATP 2.- Adenosine diphosphate interacts with an reduced thioredoxin through a ribonucleoside diphosphate reductase 1 resulting in a release of a water molecule, a oxidized thioredoxin and a dADP. The dADP is then phosphorylated by a nucleoside diphosphate kinase resulting in the release of ADP and a dATP 3.- Adenosine diphosphate interacts with an reduced NrdH glutaredoxin-like protein through a ribonucleoside diphosphate reductase 2 resulting in a release of a water molecule, a oxidized glutaredoxin-like protein and a dADP. The dADP is then phosphorylated by a nucleoside diphosphate kinase resulting in the release of ADP and a dATP PW000910 Metabolic purine nucleotides de novo biosynthesis 1435709748 PW000960 Metabolic purine nucleotides de novo biosynthesis 2 The biosynthesis of purine nucleotides is a complex process that begins with a phosphoribosyl pyrophosphate. This compound interacts with water and L-glutamine through a amidophosphoribosyl transferase resulting in a pyrophosphate, L-glutamic acid and a 5-phosphoribosylamine. The latter compound proceeds to interact with a glycine through an ATP driven phosphoribosylamine-glycine ligase resulting in the addition of glycine to the compound. This reaction releases an ADP, a phosphate, a hydrogen ion and a N1-(5-phospho-β-D-ribosyl)glycinamide. The latter compound interacts with formic acid, through an ATP driven phosphoribosylglycinamide formyltransferase 2 resulting in a phosphate, an ADP, a hydrogen ion and a 5-phosphoribosyl-N-formylglycinamide. The latter compound interacts with L-glutamine, and water through an ATP-driven phosphoribosylformylglycinamide synthetase resulting in a release of a phosphate, an ADP, a hydrogen ion, a L-glutamic acid and a 2-(formamido)-N1-(5-phospho-D-ribosyl)acetamidine. The latter compound interacts with an ATP driven phosphoribosylformylglycinamide cyclo-ligase resulting in a release of ADP, a phosphate, a hydrogen ion and a 5-aminoimidazole ribonucleotide. The latter compound interacts with a hydrogen carbonate through an ATP driven N5-carboxyaminoimidazole ribonucleotide synthetase resulting in a release of a phosphate, an ADP, a hydrogen ion and a N5-carboxyaminoimidazole ribonucleotide(5-Phosphoribosyl-5-carboxyaminoimidazole).The latter compound then interacts with a N5-carboxyaminoimidazole ribonucleotide mutase resulting in a 5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylate. This compound interacts with an L-aspartic acid through an ATP driven phosphoribosylaminoimidazole-succinocarboxamide synthase resulting in a phosphate, an ADP, a hydrogen ion and a SAICAR. SAICAR interacts with an adenylosuccinate lyase resulting in a fumaric acid and an AICAR. AICAR interacts with a formyltetrahydrofolate through a AICAR transformylase / IMP cyclohydrolase resulting in a release of a tetrahydropterol mono-l-glutamate and a FAICAR. The latter compound, FAICAR, interacts in a reversible reaction through a AICAR transformylase / IMP cyclohydrolase resulting in a release of water and Inosinic acid. Inosinic acid can be metabolized to produce dGTP and dATP three different methods each. dGTP: Inosinic acid, water and NAD are processed by IMP dehydrogenase resulting in a release of NADH, a hydrogen ion and Xanthylic acid. Xanthylic acid interacts with L-glutamine, and water through an ATP driven GMP synthetase resulting in pyrophosphate, AMP, L-glutamic acid, a hydrogen ion and Guanosine monophosphate. The latter compound is the phosphorylated by reacting with an ATP driven guanylate kinase resulting in a release of ADP and a Gaunosine diphosphate. Guanosine diphosphate can be metabolized in three different ways: 1.-Guanosine diphosphate is phosphorylated by an ATP-driven nucleoside diphosphate kinase resulting in an ADP and a Guanosine triphosphate. This compound interacts with a reduced flavodoxin protein through a ribonucleoside-triphosphate reductase resulting in a oxidized flavodoxin a water moleculer and a dGTP 2.-Guanosine diphosphate interacts with a reduced NrdH glutaredoxin-like proteins through a ribonucleoside-diphosphate reductase 2 resulting in the release of an oxidized NrdH glutaredoxin-like protein, a water molecule and a dGDP. The dGDP is then phosphorylated by interacting with an ATP-driven nucleoside diphosphate kinase resulting in an ADP and dGTP. 3.-Guanosine diphosphate interacts with a reduced thioredoxin ribonucleoside diphosphate reductase 1 resulting in a release of a water molecule, an oxidized thioredoxin and a dGDP. The dGDP is then phosphorylated by interacting with an ATP-driven nucleoside diphosphate kinase resulting in an ADP and dGTP. dATP: Inosinic acid interacts with L-aspartic acid through an GTP driven adenylosuccinate synthase results in the release of GDP, a hydrogen ion, a phosphate and N(6)-(1,2-dicarboxyethyl)AMP. The latter compound is then cleaved by a adenylosuccinate lyase resulting in a fumaric acid and an Adenosine monophosphate. This compound is then phosphorylated by an adenylate kinase resulting in the release of ATP and an adenosine diphosphate. Adenosine diphosphate can be metabolized in three different ways: 1.-Adenosine diphosphate is involved in a reversible reaction by interacting with a hydrogen ion and a phosphate through a ATP synthase / thiamin triphosphate synthase resulting in a hydrogen ion, a water molecule and an Adenosine triphosphate. The adenosine triphosphate interacts with a reduced flavodoxin through a ribonucleoside-triphosphate reductase resulting in an oxidized flavodoxin, a water molecule and a dATP 2.- Adenosine diphosphate interacts with an reduced thioredoxin through a ribonucleoside diphosphate reductase 1 resulting in a release of a water molecule, a oxidized thioredoxin and a dADP. The dADP is then phosphorylated by a nucleoside diphosphate kinase resulting in the release of ADP and a dATP 3.- Adenosine diphosphate interacts with an reduced NrdH glutaredoxin-like protein through a ribonucleoside diphosphate reductase 2 resulting in a release of a water molecule, a oxidized glutaredoxin-like protein and a dADP. The dADP is then phosphorylated by a nucleoside diphosphate kinase resulting in the release of ADP and a dATP PW002033 Metabolic purine ribonucleosides degradation Purine ribonucleoside degradation leads to the production of alpha-D-ribose-1-phosphate. Xanthosine is transported into the cytosol through a xapB. Once in the cytosol xanthosine interacts with phosphate through a xanthosine phosphorylase resulting in the release of a xanthine and a alpha-D-ribose-1-phosphate. Adenosine is transported through a nupC or a nupG transporter, once inside the cytosol it can either react with a phosphate through a adenosine phosphorylase resultin in the release of a adenine and an alpha-D-ribose-1-phosphate. Adenosine reacts with water and hydrogen ion through a adenosine deaminase resulting in the release of ammonium and inosine. Inosine reacts with phosphate through a inosine phosphorylase resulting in the release of a hypoxanthine and an alpha-D-ribose-1-phosphate. Guanosine reacts with a phosphate through a guanosine phosphorylase resulting in the release of a guanine and a alpha-D-ribose-1-phosphate. PW002076 Metabolic guanosine nucleotides <i>de novo</i> biosynthesis PWY-6125 xanthine and xanthosine salvage SALVPURINE2-PWY Specdb::CMs 21052 Specdb::CMs 38124 Specdb::CMs 174138 Specdb::NmrOneD 148200 Specdb::NmrOneD 148201 Specdb::NmrOneD 148202 Specdb::NmrOneD 148203 Specdb::NmrOneD 148204 Specdb::NmrOneD 148205 Specdb::NmrOneD 148206 Specdb::NmrOneD 148207 Specdb::NmrOneD 148208 Specdb::NmrOneD 148209 Specdb::NmrOneD 148210 Specdb::NmrOneD 148211 Specdb::NmrOneD 148212 Specdb::NmrOneD 148213 Specdb::NmrOneD 148214 Specdb::NmrOneD 148215 Specdb::NmrOneD 148216 Specdb::NmrOneD 148217 Specdb::NmrOneD 148218 Specdb::NmrOneD 148219 Specdb::MsMs 27155 Specdb::MsMs 27156 Specdb::MsMs 27157 Specdb::MsMs 33713 Specdb::MsMs 33714 Specdb::MsMs 33715 Specdb::MsMs 439122 Specdb::MsMs 448073 Specdb::MsMs 2226799 Specdb::MsMs 2227894 Specdb::MsMs 2229163 Specdb::MsMs 2230311 Specdb::MsMs 2231585 Specdb::MsMs 2232588 Specdb::MsMs 2234037 Specdb::MsMs 2234921 Specdb::MsMs 2252812 Specdb::MsMs 2253686 Specdb::MsMs 2316233 Specdb::MsMs 2316234 Specdb::MsMs 2316235 Specdb::MsMs 2623181 Specdb::MsMs 2623182 Specdb::MsMs 2623183 HMDB01554 1190 66054 C00655 15652 XANTHOSINE-5-PHOSPHATE XMP XMP Keseler, I. 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Kokai Tokkyo Koho (1985), 3 pp. GMP synthase [glutamine-hydrolyzing] P04079 GUAA_ECOLI guaA http://ecmdb.ca/proteins/P04079.xml Protein ushA P07024 USHA_ECOLI ushA http://ecmdb.ca/proteins/P07024.xml Multifunctional protein surE P0A840 SURE_ECOLI surE http://ecmdb.ca/proteins/P0A840.xml 5'-nucleotidase yjjG P0A8Y1 YJJG_ECOLI yjjG http://ecmdb.ca/proteins/P0A8Y1.xml Hypoxanthine phosphoribosyltransferase P0A9M2 HPRT_ECOLI hpt http://ecmdb.ca/proteins/P0A9M2.xml Xanthine phosphoribosyltransferase P0A9M5 XGPT_ECOLI gpt http://ecmdb.ca/proteins/P0A9M5.xml Inosine-5'-monophosphate dehydrogenase P0ADG7 IMDH_ECOLI guaB http://ecmdb.ca/proteins/P0ADG7.xml Class B acid phosphatase P0AE22 APHA_ECOLI aphA http://ecmdb.ca/proteins/P0AE22.xml Nucleoside-triphosphatase rdgB P52061 RDGB_ECOLI rdgB http://ecmdb.ca/proteins/P52061.xml 5'-nucleotidase yfbR P76491 YFBR_ECOLI yfbR http://ecmdb.ca/proteins/P76491.xml Outer membrane protein N P77747 OMPN_ECOLI ompN http://ecmdb.ca/proteins/P77747.xml Outer membrane pore protein E P02932 PHOE_ECOLI phoE http://ecmdb.ca/proteins/P02932.xml Outer membrane protein F P02931 OMPF_ECOLI ompF http://ecmdb.ca/proteins/P02931.xml Outer membrane protein C P06996 OMPC_ECOLI ompC http://ecmdb.ca/proteins/P06996.xml Water + Xanthylic acid > Phosphate + Xanthosine Phosphoribosyl pyrophosphate + Xanthine <> Pyrophosphate + Xanthylic acid R02142 XANPRIBOSYLTRAN-RXN Adenosine triphosphate + L-Glutamine + Water + Xanthylic acid > Adenosine monophosphate + L-Glutamate + Guanosine monophosphate +2 Hydrogen ion + Pyrophosphate R01231 GMP-SYN-GLUT-RXN Water + Inosinic acid + NAD <> Hydrogen ion + NADH + Xanthylic acid R01130 IMP-DEHYDROG-RXN Water + Xanthosine 5-triphosphate > Hydrogen ion + Pyrophosphate + Xanthylic acid R02720 RXN0-1603 Adenosine triphosphate + Xanthylic acid + Ammonia <> Adenosine monophosphate + Pyrophosphate + Guanosine monophosphate R01230 Adenosine triphosphate + Xanthylic acid + L-Glutamine + Water <> Adenosine monophosphate + Pyrophosphate + Guanosine monophosphate + L-Glutamate R01231 Xanthylic acid + Pyrophosphate <> Xanthine + Phosphoribosyl pyrophosphate R02142 Xanthylic acid + Water <> Xanthosine + Phosphate R02719 Xanthosine 5-triphosphate + Water <> Xanthylic acid + Pyrophosphate R02720 Water + L-Glutamine + Xanthylic acid + Adenosine triphosphate > Hydrogen ion + L-Glutamate + Guanosine monophosphate + Pyrophosphate + Adenosine monophosphate R01231 GMP-SYN-GLUT-RXN Adenosine triphosphate + Xanthylic acid + Ammonia > Hydrogen ion + Adenosine monophosphate + Pyrophosphate + Guanosine monophosphate R01230 GMP-SYN-NH3-RXN Water + NAD + Inosinic acid > Hydrogen ion + NADH + Xanthylic acid R01130 IMP-DEHYDROG-RXN Xanthylic acid + Pyrophosphate < Xanthine + Phosphoribosyl pyrophosphate R02142 XANPRIBOSYLTRAN-RXN 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 R02720 Adenosine triphosphate + Xanthylic acid + L-Glutamine + Water + Ammonia <> Adenosine monophosphate + Pyrophosphate + Guanosine monophosphate + L-Glutamate R01231 Xanthylic acid + Adenosine triphosphate + L-Glutamine + Water > Adenosine monophosphate + Pyrophosphate + L-Glutamic acid +2 Hydrogen ion + Guanosine monophosphate + L-Glutamate PW_R003427 Xanthine + Phosphoribosyl pyrophosphate > Xanthylic acid + Pyrophosphate PW_R006088 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