2.0 2012-05-31 13:48:06 -0600 2015-06-03 15:53:52 -0600 ECMDB01235 M2MDB000306 5-Aminoimidazole ribonucleotide 5-aminoimidazole ribonucleotide (AIR), is an intermediate of purine nucleotide biosynthesis, the precursor to 4-amino-2-methyl-5-hydroxymethylpyrimidine (HMP), the first product of the pyrimidine biosynthesis in a reaction mediated by the enzyme HMP-P kinase (ThiD). HMP is a precursor of thiamin phosphate (TMP), and subsequently to thiamin pyrophosphate (TPP), an essential cofactor in all living systems that plays a central role in metabolism. (PMID: 15326535) 5-Aminoimidazole ribonucleotide is a substrate for Scaffold attachment factor B2, Multifunctional protein ADE2, Serine/threonine-protein kinase Chk1, Vinexin, Trifunctional purine biosynthetic protein adenosine-3, Antileukoproteinase 1 and Scaffold attachment factor B. 1-(5'-Phosphoribosyl)-5-aminoimidazole 1-(5-Phospho-D-ribosyl)-5-aminoimidazole 5'-Phosphoribosyl-5-aminoimidazole 5-Amino-1-(5-phospho-D-ribosyl)imidazole 5-Amino-1-(5-phospho-β-D-ribosyl)imidazole 5-Aminoimidazole ribonucleotide 5-Aminoimidazole ribotide AIR Aminoimidazole ribotide Phosphoribosylaminoimidazole C8H14N3O7P 295.1864 295.056936329 {[(2R,3S,4R,5R)-5-(5-amino-1H-imidazol-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid 5-aminoimidazole ribotide 25635-88-5 NC1=CN=CN1[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O InChI=1S/C8H14N3O7P/c9-5-1-10-3-11(5)8-7(13)6(12)4(18-8)2-17-19(14,15)16/h1,3-4,6-8,12-13H,2,9H2,(H2,14,15,16)/t4-,6-,7-,8-/m1/s1 PDACUKOKVHBVHJ-XVFCMESISA-N Solid Cytosol logp -2.27 ALOGPS logs -1.94 ALOGPS solubility 3.38e+00 g/l ALOGPS logp -4.3 ChemAxon pka_strongest_acidic 1.22 ChemAxon pka_strongest_basic 7.92 ChemAxon iupac {[(2R,3S,4R,5R)-5-(5-amino-1H-imidazol-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid ChemAxon average_mass 295.1864 ChemAxon mono_mass 295.056936329 ChemAxon smiles NC1=CN=CN1[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O ChemAxon formula C8H14N3O7P ChemAxon inchi InChI=1S/C8H14N3O7P/c9-5-1-10-3-11(5)8-7(13)6(12)4(18-8)2-17-19(14,15)16/h1,3-4,6-8,12-13H,2,9H2,(H2,14,15,16)/t4-,6-,7-,8-/m1/s1 ChemAxon inchikey PDACUKOKVHBVHJ-XVFCMESISA-N ChemAxon polar_surface_area 160.29 ChemAxon refractivity 60.44 ChemAxon polarizability 24.79 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 8 ChemAxon donor_count 5 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Purine metabolism ec00230 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 Thiamin diphosphate biosynthesis PW002028 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 superpathway of 5-aminoimidazole ribonucleotide biosynthesis PWY-6277 5-aminoimidazole ribonucleotide biosynthesis I PWY-6121 5-aminoimidazole ribonucleotide biosynthesis II PWY-6122 4-amino-2-methyl-5-diphosphomethylpyrimidine biosynthesis PWY-6890 inosine-5'-phosphate biosynthesis I PWY-6123 Specdb::CMs 2889 Specdb::CMs 37987 Specdb::CMs 169775 Specdb::NmrOneD 8942 Specdb::NmrOneD 8943 Specdb::NmrOneD 8944 Specdb::NmrOneD 8945 Specdb::NmrOneD 8946 Specdb::NmrOneD 8947 Specdb::NmrOneD 8948 Specdb::NmrOneD 8949 Specdb::NmrOneD 8950 Specdb::NmrOneD 8951 Specdb::NmrOneD 8952 Specdb::NmrOneD 8953 Specdb::NmrOneD 8954 Specdb::NmrOneD 8955 Specdb::NmrOneD 8956 Specdb::NmrOneD 8957 Specdb::NmrOneD 8958 Specdb::NmrOneD 8959 Specdb::NmrOneD 8960 Specdb::NmrOneD 8961 Specdb::MsMs 23300 Specdb::MsMs 23301 Specdb::MsMs 23302 Specdb::MsMs 30098 Specdb::MsMs 30099 Specdb::MsMs 30100 Specdb::MsMs 3049700 Specdb::MsMs 3049701 Specdb::MsMs 3049702 Specdb::MsMs 3117806 Specdb::MsMs 3117807 Specdb::MsMs 3117808 HMDB01235 161500 141854 C03373 28843 5-PHOSPHORIBOSYL-5-AMINOIMIDAZOLE AIR 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 Lawhorn, B. G., Mehl, R. A., Begley, T. P. (2004). "Biosynthesis of the thiamin pyrimidine: the reconstitution of a remarkable rearrangement reaction." 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Phosphoribosylformylglycinamidine cyclo-ligase P08178 PUR5_ECOLI purM http://ecmdb.ca/proteins/P08178.xml Phosphoribosylaminoimidazole carboxylase ATPase subunit P09029 PURK_ECOLI purK http://ecmdb.ca/proteins/P09029.xml Phosphomethylpyrimidine synthase P30136 THIC_ECOLI thiC http://ecmdb.ca/proteins/P30136.xml 5-Aminoimidazole ribonucleotide + Adenosine triphosphate + Hydrogen carbonate > 5-Phosphoribosyl-5-carboxyaminoimidazole + ADP + Hydrogen ion + Phosphate Adenosine triphosphate + Phosphoribosylformylglycineamidine <> ADP + 5-Aminoimidazole ribonucleotide +2 Hydrogen ion + Phosphate R04208 AIRS-RXN 5-Aminoimidazole ribonucleotide + Water + NAD > 4-Amino-2-methyl-5-phosphomethylpyrimidine +2 Formic acid +3 Hydrogen ion + NADH 4-Amino-5-hydroxymethyl-2-methylpyrimidine + S-Adenosylmethionine <> 5-Aminoimidazole ribonucleotide + 4-Amino-2-methyl-5-phosphomethylpyrimidine + 5'-Deoxyadenosine + L-Methionine + Formic acid + CO R03472 Adenosine triphosphate + Phosphoribosylformylglycineamidine <> ADP + Phosphate + 5-Aminoimidazole ribonucleotide R04208 Adenosine triphosphate + 5-Aminoimidazole ribonucleotide + Hydrogen carbonate <> ADP + Phosphate + 5-Carboxyamino-1-(5-phospho-D-ribosyl)imidazole + 5-carboxyamino-1-(5-phospho-D-ribosyl)imidazole R07404 Adenosine triphosphate + Phosphoribosylformylglycineamidine > Hydrogen ion + ADP + Phosphate + 5-Aminoimidazole ribonucleotide R04208 AIRS-RXN 5-Aminoimidazole ribonucleotide + S-Adenosylmethionine 4-Amino-2-methyl-5-phosphomethylpyrimidine + 5'-Deoxyadenosine + L-Methionine + Formic acid + carbon monoxide + Hydrogen ion PYRIMSYN1-RXN 5-Aminoimidazole ribonucleotide + Adenosine triphosphate + Hydrogen carbonate > Hydrogen ion + N5-Carboxyaminoimidazole ribonucleotide + ADP + Phosphate RXN0-742 Adenosine triphosphate + 2-(Formamido)-N(1)-(5-phospho-D-ribosyl)acetamidine > ADP + Inorganic phosphate + 5-Aminoimidazole ribonucleotide Adenosine triphosphate + 5-Aminoimidazole ribonucleotide + Carbonic acid > ADP + Inorganic phosphate + 5-carboxyamino-1-(5-phospho-D-ribosyl)imidazole 5-Aminoimidazole ribonucleotide + S-adenosyl-L-methionine > 4-Amino-2-methyl-5-phosphomethylpyrimidine + 5'-Deoxyadenosine + L-Methionine + Formic acid + CO 5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylate <> 5-Aminoimidazole ribonucleotide + Carbon dioxide R04209 2-(Formamido)-N1-(5-phospho-D-ribosyl)acetamidine + Adenosine triphosphate > 5-Aminoimidazole ribonucleotide + Phosphate + Adenosine diphosphate + Hydrogen ion + ADP PW_R003414 5-Aminoimidazole ribonucleotide + Hydrogen carbonate + Adenosine triphosphate > N5-Carboxyaminoimidazole ribonucleotide + Adenosine diphosphate + Phosphate +2 Hydrogen ion + N5-Carboxyaminoimidazole ribonucleotide + ADP PW_R003417 5-Aminoimidazole ribonucleotide + S-adenosyl-L-methionine >3 Hydrogen ion + CO + Formic acid + L-Methionine + 5'-Deoxyadenosine + 4-amino-2-methyl-5-phosphomethylpyrimidine PW_R005931 Adenosine triphosphate + Phosphoribosylformylglycineamidine <> ADP +5 5-Aminoimidazole ribonucleotide +2 Hydrogen ion + Phosphate 4 4-Amino-5-hydroxymethyl-2-methylpyrimidine + S-Adenosylmethionine <>5 5-Aminoimidazole ribonucleotide +4 4-Amino-2-methyl-5-phosphomethylpyrimidine +5 5'-Deoxyadenosine + L-Methionine + Formic acid + CO Adenosine triphosphate + 5 5-Aminoimidazole ribonucleotide + Hydrogen carbonate <> ADP + Phosphate +5 5-carboxyamino-1-(5-phospho-D-ribosyl)imidazole 4 4-Amino-5-hydroxymethyl-2-methylpyrimidine + S-Adenosylmethionine <>5 5-Aminoimidazole ribonucleotide +4 4-Amino-2-methyl-5-phosphomethylpyrimidine +5 5'-Deoxyadenosine + L-Methionine + Formic acid + CO