2.0 2012-05-31 13:01:12 -0600 2015-09-17 15:41:06 -0600 ECMDB00797 M2MDB000186 SAICAR SAICAR (or (S)-2-[5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamido]succinate) is a substrate for the multifunctional protein ADE2. SAICAR is an intermediate in purine metabolism. (S)-2-[5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamido]succinate is converted from 5-Amino-1-(5-phospho-D-ribosyl) imidazole-4-carboxylate via phosphoribosylaminoimidazole-succinocarboxamide synthase [EC: 6.3.2.6] or SAICAR synthase. This enzyme catalyses the seventh step out of ten in the biosynthesis of purine nucleotides. (Wikipedia) (<i>S</i>)-2-[5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamido]succinate (S)-2-(5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamido)succinate (S)-2-(5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamido)succinic acid (S)-2-(5-amino-1-(5-phospho-delta-ribosyl)imidazole-4-carboxamido)succinate (S)-2-(5-amino-1-(5-phospho-delta-ribosyl)imidazole-4-carboxamido)succinic acid (S)-2-(5-amino-1-(5-phospho-δ-Ribosyl)imidazole-4-carboxamido)succinate (S)-2-(5-amino-1-(5-phospho-δ-Ribosyl)imidazole-4-carboxamido)succinic acid (S)-2-[5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamido]succinate (S)-2-[5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamido]succinic acid (S)-2-[5-Amino-1-(5-phospho-delta-ribosyl)imidazole-4-carboxamido]succinate (S)-2-[5-Amino-1-(5-phospho-delta-ribosyl)imidazole-4-carboxamido]succinic acid (S)-2-[5-amino-1-(5-phospho-δ-Ribosyl)imidazole-4-carboxamido]succinate (S)-2-[5-amino-1-(5-phospho-δ-Ribosyl)imidazole-4-carboxamido]succinic acid 1-(5'-Phosphoribosyl)-4-(N-succino-carboxamide)-5-aminoimidazole 1-(5'-Phosphoribosyl)-4-(N-succinocarboxamide)-5-aminoimidazole 1-(5'-Phosphoribosyl)-5-amino-4-(N-succinocarboxamide)-imidazole 1-(5'-Phosphoribosyl)-5-amino-4-(N-succinocarboxamide)-imidazole' 1-(5'-Phosphoribosyl)-4-(N-succinocarboxamide)-5-aminoimidazole 1-(5-Phosphoribosyl)-4-(N-succino-carboxamide)-5-aminoimidazole 5'-p-Ribosyl-4-(N-succinocarboxamide)-5-amino imidazole 5'-P-Ribosyl-4-(N-succinocarboxamide)-5-aminoimidazole 5'-Phosphoribosyl-4-(N-succinocarboxamide)-5-aminoimidazole 5'-Phosphoribosyl-4-(N-succinocarbozamide)-5-aminoimidazole 5-Amino-4-imidazole-N-succinocarboxamide ribonucleotide L-N-[(5-Amino-1-b-D-ribofuranosylimidazol-4-yl)carbonyl]-5'-(dihydrogen phosphate) L-N-[(5-amino-1-b-D-Ribofuranosylimidazol-4-yl)carbonyl]-5'-(dihydrogen phosphoric acid) L-N-[(5-amino-1-b-delta-Ribofuranosylimidazol-4-yl)carbonyl]-5'-(dihydrogen phosphate) L-N-[(5-amino-1-b-delta-Ribofuranosylimidazol-4-yl)carbonyl]-5'-(dihydrogen phosphoric acid) L-N-[(5-amino-1-b-δ-Ribofuranosylimidazol-4-yl)carbonyl]-5'-(dihydrogen phosphate) L-N-[(5-amino-1-b-δ-Ribofuranosylimidazol-4-yl)carbonyl]-5'-(dihydrogen phosphoric acid) L-N-[(5-Amino-1-beta-delta-ribofuranosylimidazol-4-yl)carbonyl]-5'-(dihydrogen phosphate) L-N-[(5-amino-1-beta-delta-Ribofuranosylimidazol-4-yl)carbonyl]-5'-(dihydrogen phosphoric acid) L-N-[(5-amino-1-β-δ-Ribofuranosylimidazol-4-yl)carbonyl]-5'-(dihydrogen phosphate) L-N-[(5-amino-1-β-δ-Ribofuranosylimidazol-4-yl)carbonyl]-5'-(dihydrogen phosphoric acid) N-(5-Amino-1-ribofuranosylimidazol-4-ylcarbonyl)aspartate 5'-phosphate N-(5-Amino-1-ribofuranosylimidazol-4-ylcarbonyl)aspartic acid 5'-phosphate N-(5-amino-1-Ribofuranosylimidazol-4-ylcarbonyl)aspartic acid 5'-phosphoric acid N-[5-Amino-1-(5'-phosphoribofuranosyl)-4-imidazolecarbonyl]aspartate N-[5-Amino-1-(5'-phosphoribofuranosyl)-4-imidazolecarbonyl]aspartic acid Phosphoribosylaminoimidazolesuccinocarboxamide SAICAR SAICAriboside Succino-AICAR Succinylaminoimidazole carboxamide riboside C13H19N4O12P 454.2833 454.073708604 (2S)-2-[({5-amino-1-[(3R,4S,5S)-3,4-dihydroxy-5-[hydroxy(phosphono)methyl]oxolan-2-yl]-1H-imidazol-4-yl}(hydroxy)methylidene)amino]butanedioic acid (2S)-2-[({5-amino-1-[(3R,4S,5S)-3,4-dihydroxy-5-[hydroxy(phosphono)methyl]oxolan-2-yl]imidazol-4-yl}(hydroxy)methylidene)amino]butanedioic acid 3031-95-6 NC1=C(N=CN1[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O)C(=O)N[C@@H](CC(O)=O)C(O)=O InChI=1S/C13H19N4O12P/c14-10-7(11(22)16-4(13(23)24)1-6(18)19)15-3-17(10)12-9(21)8(20)5(29-12)2-28-30(25,26)27/h3-5,8-9,12,20-21H,1-2,14H2,(H,16,22)(H,18,19)(H,23,24)(H2,25,26,27)/t4-,5+,8+,9+,12+/m0/s1 NAQGHJTUZRHGAC-ZZZDFHIKSA-N Solid Cytosol logp -1.79 ALOGPS logs -1.98 ALOGPS solubility 4.72e+00 g/l ALOGPS logp -5.9 ChemAxon pka_strongest_acidic 1.25 ChemAxon pka_strongest_basic 7.08 ChemAxon iupac (2S)-2-[({5-amino-1-[(3R,4S,5S)-3,4-dihydroxy-5-[hydroxy(phosphono)methyl]oxolan-2-yl]-1H-imidazol-4-yl}(hydroxy)methylidene)amino]butanedioic acid ChemAxon average_mass 454.2833 ChemAxon mono_mass 454.073708604 ChemAxon smiles NC1=C(N=CN1[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O)C(=O)N[C@@H](CC(O)=O)C(O)=O ChemAxon formula C13H19N4O12P ChemAxon inchi InChI=1S/C13H19N4O12P/c14-10-7(11(22)16-4(13(23)24)1-6(18)19)15-3-17(10)12-9(21)8(20)5(29-12)2-28-30(25,26)27/h3-5,8-9,12,20-21H,1-2,14H2,(H,16,22)(H,18,19)(H,23,24)(H2,25,26,27)/t4-,5+,8+,9+,12+/m0/s1 ChemAxon inchikey NAQGHJTUZRHGAC-ZZZDFHIKSA-N ChemAxon polar_surface_area 278.48 ChemAxon refractivity 90.71 ChemAxon polarizability 38.81 ChemAxon rotatable_bond_count 8 ChemAxon acceptor_count 15 ChemAxon donor_count 9 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon Alanine, aspartate and glutamate metabolism ec00250 Purine metabolism ec00230 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 inosine-5'-phosphate biosynthesis I PWY-6123 Specdb::MsMs 27485 Specdb::MsMs 27486 Specdb::MsMs 27487 Specdb::MsMs 34043 Specdb::MsMs 34044 Specdb::MsMs 34045 HMDB00797 160666 141175 C04823 18319 P-RIBOSYL-4-SUCCCARB-AMINOIMIDAZOLE 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 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. 18331064 Shaw, Gordon; Thomas, Peter S.; Patey, Carole A. H.; Thomas, Susan E. Purines, pyrimidines and imidazoles. Part 50. Inhibition of adenylosuccinate AMP-lyase no. 4.3.2.2. by derivatives of N-(5-amino-1-b-D-ribofuranosylimidazole-4-carbonyl)-L-aspartic a Phosphoribosylaminoimidazole-succinocarboxamide synthase P0A7D7 PUR7_ECOLI purC http://ecmdb.ca/proteins/P0A7D7.xml Adenylosuccinate lyase P0AB89 PUR8_ECOLI purB http://ecmdb.ca/proteins/P0AB89.xml SAICAR <> Phosphoribosyl formamidocarboxamide + Fumaric acid 5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylate + L-Aspartic acid + Adenosine triphosphate <> SAICAR + ADP + Hydrogen ion + Phosphate R04591 SAICARSYN-RXN SAICAR <> Fumaric acid + AICAR R04559 Adenosine triphosphate + 5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylate + L-Aspartic acid <> ADP + Phosphate + SAICAR R04591 SAICAR > Fumaric acid + AICAR R04559 AICARSYN-RXN Adenosine triphosphate + 5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylate + L-Aspartic acid > Hydrogen ion + ADP + Phosphate + SAICAR R04591 SAICARSYN-RXN Adenosine triphosphate + 5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylate + L-Aspartic acid > ADP + Inorganic phosphate + SAICAR Adenylsuccinic acid + SAICAR <> Fumaric acid + Adenosine monophosphate + AICAR R01083 5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylate + L-Aspartic acid + Adenosine triphosphate + L-Aspartic acid > SAICAR + Phosphate + Adenosine diphosphate + Hydrogen ion + SAICAR + ADP PW_R003419 SAICAR + SAICAR > AICAR + Fumaric acid PW_R003420 5 5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylate + L-Aspartic acid + Adenosine triphosphate <> SAICAR + ADP + Hydrogen ion + Phosphate SAICAR <> Fumaric acid + AICAR 5 5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylate + L-Aspartic acid + Adenosine triphosphate <> SAICAR + ADP + Hydrogen ion + Phosphate