2.02012-05-31 14:21:30 -06002015-06-03 17:19:04 -0600ECMDB12277M2MDB000837PhosphoribosylformiminoAICAR-phosphatePhosphoribosylformiminoaicar-phosphate is a member of the chemical class known as 1-Phosphoribosyl-imidazolecarboxamides. These are organic compounds containing the imidazolecarboxamide linked to a ribose phosphate through a 1-2 bond. 5-(5'-Phospho-D-ribosyl-aminoformimino)-1-(5-phosphoribosyl)-imidazole-4-carboxamide5-(5-Phospho-D-ribosyl-aminoformimino)-1-(5-phosphoribosyl)-imidazole4-carboxamideN-(5'-Phospho-D-ribosylformimino)-5-amino-1-(5''-phosphoribosyl)-4-imidazolecarboxamideN-5-Phosphoribosyl-formimino-5-amino-imidazole-4-carboxamide ribonucleotidePhosphoribosyl-formimino-aicar-pPhosphoribosylformiminoaicar-pPhosphoribosylformiminoAICAR-phosphatePhosphoribosylformiminoAICAR-phosphoric acidPRFAPC15H25N5O15P2577.331577.082238179({5-[(E)-N'-(4-carbamoyl-1-{3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl}-1H-imidazol-5-yl)imidamido]-3,4-dihydroxyoxolan-2-yl}methoxy)phosphonic acid{5-[(E)-N'-(5-carbamoyl-3-{3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl}imidazol-4-yl)imidamido]-3,4-dihydroxyoxolan-2-yl}methoxyphosphonic acidNC(=O)C1=C(\N=C\NC2OC(COP(O)(O)=O)C(O)C2O)N(C=N1)C1OC(COP(O)(O)=O)C(O)C1OInChI=1S/C15H25N5O15P2/c16-12(25)7-13(17-3-18-14-10(23)8(21)5(34-14)1-32-36(26,27)28)20(4-19-7)15-11(24)9(22)6(35-15)2-33-37(29,30)31/h3-6,8-11,14-15,21-24H,1-2H2,(H2,16,25)(H,17,18)(H2,26,27,28)(H2,29,30,31)QOUSHGMTBIIAHR-UHFFFAOYSA-NSolidCytosollogp-1.76logs-2.00solubility5.75e+00 g/llogp-5.5pka_strongest_acidic1.21pka_strongest_basic6.75iupac({5-[(E)-N'-(4-carbamoyl-1-{3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl}-1H-imidazol-5-yl)imidamido]-3,4-dihydroxyoxolan-2-yl}methoxy)phosphonic acidaverage_mass577.331mono_mass577.082238179smilesNC(=O)C1=C(\N=C\NC2OC(COP(O)(O)=O)C(O)C2O)N(C=N1)C1OC(COP(O)(O)=O)C(O)C1OformulaC15H25N5O15P2inchiInChI=1S/C15H25N5O15P2/c16-12(25)7-13(17-3-18-14-10(23)8(21)5(34-14)1-32-36(26,27)28)20(4-19-7)15-11(24)9(22)6(35-15)2-33-37(29,30)31/h3-6,8-11,14-15,21-24H,1-2H2,(H2,16,25)(H,17,18)(H2,26,27,28)(H2,29,30,31)inchikeyQOUSHGMTBIIAHR-UHFFFAOYSA-Npolar_surface_area318.2refractivity114.57polarizability48.56rotatable_bond_count10acceptor_count16donor_count10physiological_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::CMs17377Specdb::CMs39895Specdb::NmrOneD330462Specdb::NmrOneD330463Specdb::NmrOneD330464Specdb::NmrOneD330465Specdb::NmrOneD330466Specdb::NmrOneD330467Specdb::NmrOneD330468Specdb::NmrOneD330469Specdb::NmrOneD330470Specdb::NmrOneD330471Specdb::NmrOneD330472Specdb::NmrOneD330473Specdb::NmrOneD330474Specdb::NmrOneD330475Specdb::NmrOneD330476Specdb::NmrOneD330477Specdb::NmrOneD330478Specdb::NmrOneD330479Specdb::NmrOneD330480Specdb::NmrOneD330481Specdb::MsMs29489Specdb::MsMs29490Specdb::MsMs29491Specdb::MsMs36047Specdb::MsMs36048Specdb::MsMs36049HMDB122771012987C04896PHOSPHORIBOSYL-FORMIMINO-AICAR-PKeseler, 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 370:17-25.17765195Histidine biosynthesis bifunctional protein hisIEP06989HIS2_ECOLIhisIhttp://ecmdb.ca/proteins/P06989.xml1-(5-phosphoribosyl)-5-[(5-phosphoribosylamino)methylideneamino] imidazole-4-carboxamide isomeraseP10371HIS4_ECOLIhisAhttp://ecmdb.ca/proteins/P10371.xmlPhosphoribosylformiminoAICAR-phosphate <> Phosphoribulosylformimino-AICAR-PR04640PRIBFAICARPISOM-RXNWater + Phosphoribosyl-AMP <> PhosphoribosylformiminoAICAR-phosphateR04037HISTCYCLOHYD-RXNPhosphoribosyl-AMP + Water > PhosphoribosylformiminoAICAR-phosphateR04037HISTCYCLOHYD-RXNPhosphoribosylformiminoAICAR-phosphate > Phosphoribulosylformimino-AICAR-PR04640PRIBFAICARPISOM-RXNAICAR > PhosphoribosylformiminoAICAR-phosphatePW_R002868Water + Phosphoribosyl-AMP <> PhosphoribosylformiminoAICAR-phosphatePhosphoribosylformiminoAICAR-phosphate <> Phosphoribulosylformimino-AICAR-P