2.0 2012-05-31 14:06:09 -0600 2015-06-03 15:54:47 -0600 ECMDB04137 M2MDB000630 Phosphoribosyl-AMP Phosphoribosyl-AMP is a nucleic acid component, a purine-related compound. It is an intermediate in histidine biosynthesis. It is converted from Phosphoribosyl-ATP via the enzyme phosphoribosyl-ATP diphosphatase (EC 3.6.1.31). It is then converted to phosphoribosylformiminoAICAR-phosphate via the enzyme phosphoribosyl-AMP cyclohydrolase (EC 3.5.4.19). 1-(5-Phosphoribosyl)-AMP 5-Phosphoribosyl-AMP N-(5'-Phospho-D-ribosyl)-AMP N-(5-Phospho-D-ribosyl)-AMP N1-(5-phospho-D-ribosyl)-AMP Phosphoribosyl-AMP PR-AMP C15H23N5O14P2 559.3157 559.071673493 {[(2R,3S,4R,5R)-5-{1-[(2S,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}phosphonic acid [(2R,3S,4R,5R)-5-{1-[(2S,3R,4S,5R)-3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]-6-iminopurin-9-yl}-3,4-dihydroxyoxolan-2-yl]methoxyphosphonic acid O[C@@H]1[C@@H](COP(O)(O)=O)O[C@H]([C@@H]1O)N1C=NC2=C1N=CN([C@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O)C2=N InChI=1S/C15H23N5O14P2/c16-12-7-13(18-4-19(12)14-10(23)8(21)5(33-14)1-31-35(25,26)27)20(3-17-7)15-11(24)9(22)6(34-15)2-32-36(28,29)30/h3-6,8-11,14-16,21-24H,1-2H2,(H2,25,26,27)(H2,28,29,30)/t5-,6-,8-,9-,10-,11-,14+,15-/m1/s1 RTQMRTSPTLIIHM-ZTRAZTMKSA-N Solid Cytosol logp -2.17 ALOGPS logs -1.94 ALOGPS solubility 6.38e+00 g/l ALOGPS logp -4.1 ChemAxon pka_strongest_acidic 0.81 ChemAxon pka_strongest_basic 5.95 ChemAxon iupac {[(2R,3S,4R,5R)-5-{1-[(2S,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}phosphonic acid ChemAxon average_mass 559.3157 ChemAxon mono_mass 559.071673493 ChemAxon smiles O[C@@H]1[C@@H](COP(O)(O)=O)O[C@H]([C@@H]1O)N1C=NC2=C1N=CN([C@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O)C2=N ChemAxon formula C15H23N5O14P2 ChemAxon inchi InChI=1S/C15H23N5O14P2/c16-12-7-13(18-4-19(12)14-10(23)8(21)5(33-14)1-31-35(25,26)27)20(3-17-7)15-11(24)9(22)6(34-15)2-32-36(28,29)30/h3-6,8-11,14-16,21-24H,1-2H2,(H2,25,26,27)(H2,28,29,30)/t5-,6-,8-,9-,10-,11-,14+,15-/m1/s1 ChemAxon inchikey RTQMRTSPTLIIHM-ZTRAZTMKSA-N ChemAxon polar_surface_area 290.17 ChemAxon refractivity 122.54 ChemAxon polarizability 47.36 ChemAxon rotatable_bond_count 8 ChemAxon acceptor_count 16 ChemAxon donor_count 9 ChemAxon physiological_charge -4 ChemAxon formal_charge 0 ChemAxon Histidine metabolism ec00340 Metabolic pathways eco01100 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::CMs 17296 Specdb::CMs 39894 Specdb::NmrOneD 286715 Specdb::NmrOneD 286716 Specdb::NmrOneD 286717 Specdb::NmrOneD 286718 Specdb::NmrOneD 286719 Specdb::NmrOneD 286720 Specdb::NmrOneD 286721 Specdb::NmrOneD 286722 Specdb::NmrOneD 286723 Specdb::NmrOneD 286724 Specdb::NmrOneD 286725 Specdb::NmrOneD 286726 Specdb::NmrOneD 286727 Specdb::NmrOneD 286728 Specdb::NmrOneD 286729 Specdb::NmrOneD 286730 Specdb::NmrOneD 286731 Specdb::NmrOneD 286732 Specdb::NmrOneD 286733 Specdb::NmrOneD 286734 Specdb::MsMs 28727 Specdb::MsMs 28728 Specdb::MsMs 28729 Specdb::MsMs 35285 Specdb::MsMs 35286 Specdb::MsMs 35287 HMDB12276 439795 C02741 PHOSPHORIBOSYL-AMP 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 Water + Phosphoribosyl-AMP <> PhosphoribosylformiminoAICAR-phosphate R04037 HISTCYCLOHYD-RXN Water + Phosphoribosyl-ATP <> Hydrogen ion + Pyrophosphate + Phosphoribosyl-AMP R04035 HISTPRATPHYD-RXN Phosphoribosyl-ATP + Water <> Phosphoribosyl-AMP + Pyrophosphate R04035 Phosphoribosyl-AMP + Water > PhosphoribosylformiminoAICAR-phosphate R04037 HISTCYCLOHYD-RXN Phosphoribosyl-ATP + Water > Hydrogen ion + Phosphoribosyl-AMP + Pyrophosphate R04035 HISTPRATPHYD-RXN Phosphoribosyl-ATP + Water + Phosphoribosyl-ATP > Hydrogen ion + Pyrophosphate + Phosphoribosyl-AMP PW_R002866 Phosphoribosyl-AMP + Water > AICAR PW_R002867 Water + Phosphoribosyl-AMP <> PhosphoribosylformiminoAICAR-phosphate