2.0 2012-05-31 14:21:33 -0600 2015-06-03 17:19:04 -0600 ECMDB12278 M2MDB000838 Phosphoribulosylformimino-AICAR-P Phosphoribulosylformimino-aicar-p 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. PRFAR is catalyzed by imidazole glycerol phosphate syntahse. Imidazole glycerol phosphate (IGP) synthase is a glutamine amidotransferase that catalyzes the formation of IGP and 5-aminoimidazole-4-carboxamide ribonucleotide (AICAR) from N(1)-[(5'-phosphoribulosyl)formimino]-5-aminoimidazole-4-car boxamide ribonucleotide (PRFAR). (PMID 10733892). 5-((5-phospho-1-deoxyribulos-1-ylamino)methylideneamino)-1-(5-phosphoribosyl)imidazole-4-carboxamide is an intermediate in the histidine biosynthesis pathway. It is a substrate for the enzyme 1-(5-phosphoribosyl)-5-[(5-phosphoribosylamino)methylideneamino] imidazole-4-carboxamide isomerase which catalyzes the reaction 1-(5-phosphoribosyl)-5-((5-phosphoribosylamino)methylideneamino)imidazole-4-carboxamide = 5-((5-phospho-1-deoxyribulos-1-ylamino)methylideneamino)-1-(5-phosphoribosyl)imidazole-4-carboxamide. 5-[(5-Phospho-1-deoxyribulos-1-ylamino)methylideneamino]-1-(5-phosphoribosyl)imidazole-4-carboxamide N-(5'-Phospho-D-1'-ribulosylformimino)-5-amino-1-(5''-phosphoribosyl)-4-imidazolecarboxamide N-(5'Phospho-D-1'-ribulosylformimino)-5-amino-1-(5-phosphoribosyl)-4-imidazolecarboxamide Phosphoribulosyl-formimino-5-aminoimidazole-4-carboxamide ribonucleotide phosphate Phosphoribulosyl-formimino-5-aminoimidazole-4-carboxamide ribonucleotide phosphoric acid Phosphoribulosyl-formimino-5-aminoimidazole-4-carboxamide ribotide phosphate Phosphoribulosyl-formimino-5-aminoimidazole-4-carboxamide ribotide phosphoric acid Phosphoribulosyl-formimino-aicar-p Phosphoribulosylformiminoaicar-phosphate Phosphoribulosylformiminoaicar-phosphoric acid Prfar PRuFAP C15H25N5O15P2 577.331 577.082238179 {[(2R,3R)-5-[(E)-N'-{4-carbamoyl-1-[(2S,3S,4R,5S)-3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]-1H-imidazol-5-yl}methenimidamido]-2,3-dihydroxy-4-oxopentyl]oxy}phosphonic acid [(2R,3R)-5-[(E)-N'-{5-carbamoyl-3-[(2S,3S,4R,5S)-3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]imidazol-4-yl}methenimidamido]-2,3-dihydroxy-4-oxopentyl]oxyphosphonic acid O[C@H](COP(=O)(O)O)[C@@H](O)C(=O)CN\C=N\C1=C(C(=O)N)N=CN1[C@H]1O[C@@H](COP(=O)(O)O)[C@H](O)[C@@H]1O InChI=1S/C15H25N5O15P2/c16-13(26)9-14(18-4-17-1-6(21)10(23)7(22)2-33-36(27,28)29)20(5-19-9)15-12(25)11(24)8(35-15)3-34-37(30,31)32/h4-5,7-8,10-12,15,22-25H,1-3H2,(H2,16,26)(H,17,18)(H2,27,28,29)(H2,30,31,32)/t7-,8+,10+,11+,12+,15+/m1/s1 BLKFNHOCHNCLII-IIZOACFYSA-N Solid Cytosol logp -1.96 ALOGPS logs -2.04 ALOGPS solubility 5.21e+00 g/l ALOGPS logp -5.7 ChemAxon pka_strongest_acidic 1.3 ChemAxon pka_strongest_basic 7.35 ChemAxon iupac {[(2R,3R)-5-[(E)-N'-{4-carbamoyl-1-[(2S,3S,4R,5S)-3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]-1H-imidazol-5-yl}methenimidamido]-2,3-dihydroxy-4-oxopentyl]oxy}phosphonic acid ChemAxon average_mass 577.331 ChemAxon mono_mass 577.082238179 ChemAxon smiles O[C@H](COP(=O)(O)O)[C@@H](O)C(=O)CN\C=N\C1=C(C(=O)N)N=CN1[C@H]1O[C@@H](COP(=O)(O)O)[C@H](O)[C@@H]1O ChemAxon formula C15H25N5O15P2 ChemAxon inchi InChI=1S/C15H25N5O15P2/c16-13(26)9-14(18-4-17-1-6(21)10(23)7(22)2-33-36(27,28)29)20(5-19-9)15-12(25)11(24)8(35-15)3-34-37(30,31)32/h4-5,7-8,10-12,15,22-25H,1-3H2,(H2,16,26)(H,17,18)(H2,27,28,29)(H2,30,31,32)/t7-,8+,10+,11+,12+,15+/m1/s1 ChemAxon inchikey BLKFNHOCHNCLII-IIZOACFYSA-N ChemAxon polar_surface_area 326.04 ChemAxon refractivity 116.21 ChemAxon polarizability 48.23 ChemAxon rotatable_bond_count 13 ChemAxon acceptor_count 16 ChemAxon donor_count 10 ChemAxon physiological_charge -3 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 23440 Specdb::CMs 39896 Specdb::NmrOneD 334418 Specdb::NmrOneD 334419 Specdb::NmrOneD 334420 Specdb::NmrOneD 334421 Specdb::NmrOneD 334422 Specdb::NmrOneD 334423 Specdb::NmrOneD 334424 Specdb::NmrOneD 334425 Specdb::NmrOneD 334426 Specdb::NmrOneD 334427 Specdb::NmrOneD 334428 Specdb::NmrOneD 334429 Specdb::NmrOneD 334430 Specdb::NmrOneD 334431 Specdb::NmrOneD 334432 Specdb::NmrOneD 334433 Specdb::NmrOneD 334434 Specdb::NmrOneD 334435 Specdb::NmrOneD 334436 Specdb::NmrOneD 334437 Specdb::MsMs 24065 Specdb::MsMs 24066 Specdb::MsMs 24067 Specdb::MsMs 30863 Specdb::MsMs 30864 Specdb::MsMs 30865 HMDB12278 1013 C04916 PHOSPHORIBULOSYL-FORMIMINO-AICAR-P 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 Chittur, S. V., Chen, Y., Davisson, V. J. (2000). "Expression and purification of imidazole glycerol phosphate synthase from Saccharomyces cerevisiae." Protein Expr Purif 18:366-377. 10733892 1-(5-phosphoribosyl)-5-[(5-phosphoribosylamino)methylideneamino] imidazole-4-carboxamide isomerase P10371 HIS4_ECOLI hisA http://ecmdb.ca/proteins/P10371.xml Imidazole glycerol phosphate synthase subunit hisH P60595 HIS5_ECOLI hisH http://ecmdb.ca/proteins/P60595.xml Imidazole glycerol phosphate synthase subunit hisF P60664 HIS6_ECOLI hisF http://ecmdb.ca/proteins/P60664.xml L-Glutamine + Phosphoribulosylformimino-AICAR-P > Phosphoribosyl formamidocarboxamide + D-Erythro-imidazole-glycerol-phosphate + L-Glutamate + Hydrogen ion PhosphoribosylformiminoAICAR-phosphate <> Phosphoribulosylformimino-AICAR-P R04640 PRIBFAICARPISOM-RXN Phosphoribulosylformimino-AICAR-P + L-Glutamine <> D-Erythro-imidazole-glycerol-phosphate + AICAR + L-Glutamate R04558 GLUTAMIDOTRANS-RXN Phosphoribulosylformimino-AICAR-P + L-Glutamine > Hydrogen ion + L-Glutamate + D-Erythro-imidazole-glycerol-phosphate + AICAR GLUTAMIDOTRANS-RXN PhosphoribosylformiminoAICAR-phosphate > Phosphoribulosylformimino-AICAR-P R04640 PRIBFAICARPISOM-RXN Phosphoribulosylformimino-AICAR-P + L-Glutamine > L-Glutamic acid + Hydrogen ion + 5-Amino-4-imidazolecarboxyamide + D-Erythro-imidazole-glycerol-phosphate + L-Glutamate PW_R002869 PhosphoribosylformiminoAICAR-phosphate <> Phosphoribulosylformimino-AICAR-P