2.02012-05-31 14:06:09 -06002015-06-03 15:54:47 -0600ECMDB04137M2MDB000630Phosphoribosyl-AMPPhosphoribosyl-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)-AMP5-Phosphoribosyl-AMPN-(5'-Phospho-D-ribosyl)-AMPN-(5-Phospho-D-ribosyl)-AMPN1-(5-phospho-D-ribosyl)-AMPPhosphoribosyl-AMPPR-AMPC15H23N5O14P2559.3157559.071673493{[(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 acidO[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=NInChI=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/s1RTQMRTSPTLIIHM-ZTRAZTMKSA-NSolidCytosollogp-2.17logs-1.94solubility6.38e+00 g/llogp-4.1pka_strongest_acidic0.81pka_strongest_basic5.95iupac{[(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 acidaverage_mass559.3157mono_mass559.071673493smilesO[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=NformulaC15H23N5O14P2inchiInChI=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/s1inchikeyRTQMRTSPTLIIHM-ZTRAZTMKSA-Npolar_surface_area290.17refractivity122.54polarizability47.36rotatable_bond_count8acceptor_count16donor_count9physiological_charge-4formal_charge0Histidine metabolismec00340Metabolic pathwayseco01100Secondary Metabolites: Histidine biosynthesisHistidine 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.PW000984Metabolichistidine biosynthesisHistidine 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.PW000810Metabolichistidine biosynthesisHISTSYN-PWYSpecdb::CMs17296Specdb::CMs39894Specdb::NmrOneD286715Specdb::NmrOneD286716Specdb::NmrOneD286717Specdb::NmrOneD286718Specdb::NmrOneD286719Specdb::NmrOneD286720Specdb::NmrOneD286721Specdb::NmrOneD286722Specdb::NmrOneD286723Specdb::NmrOneD286724Specdb::NmrOneD286725Specdb::NmrOneD286726Specdb::NmrOneD286727Specdb::NmrOneD286728Specdb::NmrOneD286729Specdb::NmrOneD286730Specdb::NmrOneD286731Specdb::NmrOneD286732Specdb::NmrOneD286733Specdb::NmrOneD286734Specdb::MsMs28727Specdb::MsMs28728Specdb::MsMs28729Specdb::MsMs35285Specdb::MsMs35286Specdb::MsMs35287HMDB12276439795C02741PHOSPHORIBOSYL-AMPKeseler, 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-D590.21097882Kanehisa, 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-D114.22080510van 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 370:17-25.17765195Winder, 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 80:2939-2948.18331064Histidine biosynthesis bifunctional protein hisIEP06989HIS2_ECOLIhisIhttp://ecmdb.ca/proteins/P06989.xmlWater + Phosphoribosyl-AMP <> PhosphoribosylformiminoAICAR-phosphateR04037HISTCYCLOHYD-RXNWater + Phosphoribosyl-ATP <> Hydrogen ion + Pyrophosphate + Phosphoribosyl-AMPR04035HISTPRATPHYD-RXNPhosphoribosyl-ATP + Water <> Phosphoribosyl-AMP + PyrophosphateR04035Phosphoribosyl-AMP + Water > PhosphoribosylformiminoAICAR-phosphateR04037HISTCYCLOHYD-RXNPhosphoribosyl-ATP + Water > Hydrogen ion + Phosphoribosyl-AMP + PyrophosphateR04035HISTPRATPHYD-RXNPhosphoribosyl-ATP + Water + Phosphoribosyl-ATP > Hydrogen ion + Pyrophosphate + Phosphoribosyl-AMPPW_R002866Phosphoribosyl-AMP + Water > AICARPW_R002867Water + Phosphoribosyl-AMP <> PhosphoribosylformiminoAICAR-phosphate