2.0 2012-05-31 14:06:12 -0600 2015-09-17 15:41:18 -0600 ECMDB04138 M2MDB000631 Phosphoribosyl-ATP Phosphoribosyl-ATP takes part in the Histidine Metabolism pathway.[KEGG ID C02739]. Specifically, Phosphoribosyl-ATP is substrate for phosphoribosyl pyrophosphate synthetase 1. 1-(5-Phospho-D-ribofuranosyl)adenosine 5'-(tetrahydrogen triphosphate) 1-(5-phospho-D-Ribofuranosyl)adenosine 5'-(tetrahydrogen triphosphoric acid) 1-(5-Phospho-D-ribosyl)-ATP 1-(5-Phosphoribosyl)-ATP 5-Phosphoribosyl-ATP N1-(5-Phospho-D-ribosyl)-ATP PR-ATP C15H26N5O20P4 720.2835 720.012159345 ({[({[(2R,3S,4R,5R)-5-{1-[(3R,4S,5R)-3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]-6-imino-6,9-dihydro-1H-purin-9-yl}-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphonic acid Phosphoribosyl-ATP NC1=[N+](C=NC2=C1N=CN2C1OC(COP(O)(=O)OP(O)(=O)OP(O)(O)=O)C(O)C1O)C1OC(COP(O)(O)=O)C(O)C1O InChI=1S/C15H25N5O20P4/c16-12-7-13(18-4-19(12)14-10(23)8(21)5(37-14)1-35-41(25,26)27)20(3-17-7)15-11(24)9(22)6(38-15)2-36-43(31,32)40-44(33,34)39-42(28,29)30/h3-6,8-11,14-16,21-24H,1-2H2,(H6,25,26,27,28,29,30,31,32,33,34)/p+1 KYTPWZMUSLPBJZ-UHFFFAOYSA-O Solid Cytosol logp -0.35 ALOGPS logs -1.86 ALOGPS solubility 9.92e+00 g/l ALOGPS logp -5 ChemAxon pka_strongest_acidic 0.66 ChemAxon pka_strongest_basic 1.71 ChemAxon iupac ({[({[(2R,3S,4R,5R)-5-{1-[(3R,4S,5R)-3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]-6-imino-6,9-dihydro-1H-purin-9-yl}-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphonic acid ChemAxon average_mass 720.2835 ChemAxon mono_mass 720.012159345 ChemAxon smiles NC1=[N+](C=NC2=C1N=CN2C1OC(COP(O)(=O)OP(O)(=O)OP(O)(O)=O)C(O)C1O)C1OC(COP(O)(O)=O)C(O)C1O ChemAxon formula C15H26N5O20P4 ChemAxon inchi InChI=1S/C15H25N5O20P4/c16-12-7-13(18-4-19(12)14-10(23)8(21)5(37-14)1-35-41(25,26)27)20(3-17-7)15-11(24)9(22)6(38-15)2-36-43(31,32)40-44(33,34)39-42(28,29)30/h3-6,8-11,14-16,21-24H,1-2H2,(H6,25,26,27,28,29,30,31,32,33,34)/p+1 ChemAxon inchikey KYTPWZMUSLPBJZ-UHFFFAOYSA-O ChemAxon polar_surface_area 383.23 ChemAxon refractivity 144.29 ChemAxon polarizability 56.94 ChemAxon rotatable_bond_count 12 ChemAxon acceptor_count 20 ChemAxon donor_count 11 ChemAxon physiological_charge -5 ChemAxon formal_charge 0 ChemAxon Histidine metabolism ec00340 Metabolic pathways eco01100 Quorum Sensing Bacterial Autoinducer 2 (AI-2) mediates the quorum sensing 2 system. AI-2 is catalyzed by the luxS enzyme. This enzyme is found in E.coli and S.typhimurium. In E. coli and most pathogenic bacteria that form AI-2 are spontaneous transformations that include cyclization to (2R,4S)-2-methyl-2,4-dihydroxydihydrofuran-3-one and hydration to the final autoinducer (2R,4S)-2-methyl-2,3,3,4-tetrahydroxytetrahydrofuran. This product is released from the cell through the AI-2 transporter (tqsA). As the level of AI-2 increases, other cells detect it and import it through the autoinducer-2 ABC transporter (lsrACDB). AI-2 is then degraded in the cells by phosphorylating the AI-2 which is then isomerized to P-HPD which follows by the transfer of and acetyl group to coenzyme A and releases dihydroxyacetone phosphate PW000836 Signaling Secondary Metabolites: Histidine biosynthesis Histidine biosynthesis starts with a product of PRPP biosynthesis pathway, phosphoribosyl pyrophosphate which interacts with a hydrogen ion through an ATP phosphoribosyltransferase resulting in an pyrophosphate and a phosphoribosyl-ATP. This compound interacts with water through a phosphoribosyl-AMP cyclohydrolase / phosphoribosyl-ATP pyrophosphatase resulting in the release of pyrophosphate, hydrogen ion and a phosphoribosyl-AMP. This enzyme proceeds to interact with phosphoribosyl-AMP and water resulting in a 1-(5'-Phosphoribosyl)-5-amino-4-imidazolecarboxamide. This compound is then isomerized by a N-(5'-phospho-L-ribosyl-formimino)-5-amino-1-(5'-phosphoribosyl)-4-imidazolecarboxamide isomerase resulting in a PhosphoribosylformiminoAICAR-phosphate. This compound reacts with L-glutamine through an imidazole glycerol phosphate synthase resulting in a L-glutamic acid, hydrogen ion, 5-aminoimidazole-4-carboxamide and a D-erythro-imidazole-glycerol-phosphate. This compound reacts with a imidazoleglycerol-phosphate dehydratase / histidinol-phosphatase, dehydrating the compound and resulting in a imidazole acetol-phosphate. This compound interacts with L-glutamic acid through a histidinol-phosphate aminotransferase, releasing oxoglutaric acid and L-histidinol-phosphate. The latter compound interacts with water and a imidazoleglycerol-phosphate dehydratase / histidinol-phosphatase resulting in L-histidinol and phosphate. L-histidinol interacts with a NAD-driven histidinol dehydrogenase resulting in a Histidinal. This in turn reacts with water in a NAD driven histidinal dehydrogenase resulting in L-Histidine. L-Histidine then represses ATP phosphoribosyltransferase, regulation its own biosynthesis. PW000984 Metabolic histidine biosynthesis Histidine biosynthesis starts with a product of PRPP biosynthesis pathway, phosphoribosyl pyrophosphate which interacts with a hydrogen ion through an ATP phosphoribosyltransferase resulting in an pyrophosphate and a phosphoribosyl-ATP. This compound interacts with water through a phosphoribosyl-AMP cyclohydrolase / phosphoribosyl-ATP pyrophosphatase resulting in the release of pyrophosphate, hydrogen ion and a phosphoribosyl-AMP. This enzyme proceeds to interact with phosphoribosyl-AMP and water resulting in a 1-(5'-Phosphoribosyl)-5-amino-4-imidazolecarboxamide. This compound is then isomerized by a N-(5'-phospho-L-ribosyl-formimino)-5-amino-1-(5'-phosphoribosyl)-4-imidazolecarboxamide isomerase resulting in a PhosphoribosylformiminoAICAR-phosphate. This compound reacts with L-glutamine through an imidazole glycerol phosphate synthase resulting in a L-glutamic acid, hydrogen ion, 5-aminoimidazole-4-carboxamide and a D-erythro-imidazole-glycerol-phosphate. This compound reacts with a imidazoleglycerol-phosphate dehydratase / histidinol-phosphatase, dehydrating the compound and resulting in a imidazole acetol-phosphate. This compound interacts with L-glutamic acid through a histidinol-phosphate aminotransferase, releasing oxoglutaric acid and L-histidinol-phosphate. The latter compound interacts with water and a imidazoleglycerol-phosphate dehydratase / histidinol-phosphatase resulting in L-histidinol and phosphate. L-histidinol interacts with a NAD-driven histidinol dehydrogenase resulting in a Histidinal. This in turn reacts with water in a NAD driven histidinal dehydrogenase resulting in L-Histidine. L-Histidine then represses ATP phosphoribosyltransferase, regulation its own biosynthesis. PW000810 Metabolic histidine biosynthesis HISTSYN-PWY Specdb::MsMs 28448 Specdb::MsMs 28449 Specdb::MsMs 28450 Specdb::MsMs 35006 Specdb::MsMs 35007 Specdb::MsMs 35008 HMDB03665 16019963 984 C02739 18263 PHOSPHORIBOSYL-ATP 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 Histidine biosynthesis bifunctional protein hisIE P06989 HIS2_ECOLI hisI http://ecmdb.ca/proteins/P06989.xml ATP phosphoribosyltransferase P60757 HIS1_ECOLI hisG http://ecmdb.ca/proteins/P60757.xml Autoinducer 2 import system permease protein lsrC B1XEA2 LSRC_ECODH lsrC http://ecmdb.ca/proteins/B1XEA2.xml Autoinducer 2 import system permease protein lsrD P0AFS1 LSRD_ECOLI lsrD http://ecmdb.ca/proteins/P0AFS1.xml Autoinducer 2 import ATP-binding protein LsrA P77257 LSRA_ECOLI lsrA http://ecmdb.ca/proteins/P77257.xml Autoinducer 2-binding protein LsrB P76142 LSRB_ECOLI lsrB http://ecmdb.ca/proteins/P76142.xml Adenosine triphosphate + Phosphoribosyl pyrophosphate <> Pyrophosphate + Phosphoribosyl-ATP R01071 ATPPHOSPHORIBOSYLTRANS-RXN Water + Phosphoribosyl-ATP <> Hydrogen ion + Pyrophosphate + Phosphoribosyl-AMP R04035 HISTPRATPHYD-RXN Phosphoribosyl-ATP + Pyrophosphate <> Adenosine triphosphate + Phosphoribosyl pyrophosphate R01071 Phosphoribosyl-ATP + Water <> Phosphoribosyl-AMP + Pyrophosphate R04035 Phosphoribosyl-ATP + Water > Hydrogen ion + Phosphoribosyl-AMP + Pyrophosphate R04035 HISTPRATPHYD-RXN Phosphoribosyl-ATP + Pyrophosphate > Adenosine triphosphate + Phosphoribosyl pyrophosphate Phosphoribosyl-ATP + Water > 1-(5-phosphoribosyl)-AMP + Pyrophosphate Phosphoribosyl pyrophosphate + Hydrogen ion > Pyrophosphate + Phosphoribosyl-ATP + Phosphoribosyl-ATP PW_R002865 Phosphoribosyl-ATP + Water + Phosphoribosyl-ATP > Hydrogen ion + Pyrophosphate + Phosphoribosyl-AMP PW_R002866 (2R,4S)-2-methyl-2,3,3,4-tetrahydroxytetrahydrofuran + Phosphoribosyl-ATP + Water + (2R,4S)-2-Methyl-2,3,3,4-tetrahydroxytetrahydrofuran + Phosphoribosyl-ATP > (2R,4S)-2-methyl-2,3,3,4-tetrahydroxytetrahydrofuran + Adenosine diphosphate + Hydrogen ion + Pyrophosphate + ADP PW_RCT000124 Adenosine triphosphate + Phosphoribosyl pyrophosphate <> Pyrophosphate + Phosphoribosyl-ATP Phosphoribosyl-ATP + Pyrophosphate <> Adenosine triphosphate + Phosphoribosyl pyrophosphate Adenosine triphosphate + Phosphoribosyl pyrophosphate <> Pyrophosphate + Phosphoribosyl-ATP