2.0 2012-05-31 14:21:30 -0600 2015-06-03 17:19:04 -0600 ECMDB12277 M2MDB000837 PhosphoribosylformiminoAICAR-phosphate Phosphoribosylformiminoaicar-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-carboxamide 5-(5-Phospho-D-ribosyl-aminoformimino)-1-(5-phosphoribosyl)-imidazole4-carboxamide N-(5'-Phospho-D-ribosylformimino)-5-amino-1-(5''-phosphoribosyl)-4-imidazolecarboxamide N-5-Phosphoribosyl-formimino-5-amino-imidazole-4-carboxamide ribonucleotide Phosphoribosyl-formimino-aicar-p Phosphoribosylformiminoaicar-p PhosphoribosylformiminoAICAR-phosphate PhosphoribosylformiminoAICAR-phosphoric acid PRFAP C15H25N5O15P2 577.331 577.082238179 ({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 acid NC(=O)C1=C(\N=C\NC2OC(COP(O)(O)=O)C(O)C2O)N(C=N1)C1OC(COP(O)(O)=O)C(O)C1O InChI=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-N Solid Cytosol logp -1.76 ALOGPS logs -2.00 ALOGPS solubility 5.75e+00 g/l ALOGPS logp -5.5 ChemAxon pka_strongest_acidic 1.21 ChemAxon pka_strongest_basic 6.75 ChemAxon iupac ({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 ChemAxon average_mass 577.331 ChemAxon mono_mass 577.082238179 ChemAxon smiles NC(=O)C1=C(\N=C\NC2OC(COP(O)(O)=O)C(O)C2O)N(C=N1)C1OC(COP(O)(O)=O)C(O)C1O ChemAxon formula C15H25N5O15P2 ChemAxon inchi InChI=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) ChemAxon inchikey QOUSHGMTBIIAHR-UHFFFAOYSA-N ChemAxon polar_surface_area 318.2 ChemAxon refractivity 114.57 ChemAxon polarizability 48.56 ChemAxon rotatable_bond_count 10 ChemAxon acceptor_count 16 ChemAxon donor_count 10 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 17377 Specdb::CMs 39895 Specdb::NmrOneD 330462 Specdb::NmrOneD 330463 Specdb::NmrOneD 330464 Specdb::NmrOneD 330465 Specdb::NmrOneD 330466 Specdb::NmrOneD 330467 Specdb::NmrOneD 330468 Specdb::NmrOneD 330469 Specdb::NmrOneD 330470 Specdb::NmrOneD 330471 Specdb::NmrOneD 330472 Specdb::NmrOneD 330473 Specdb::NmrOneD 330474 Specdb::NmrOneD 330475 Specdb::NmrOneD 330476 Specdb::NmrOneD 330477 Specdb::NmrOneD 330478 Specdb::NmrOneD 330479 Specdb::NmrOneD 330480 Specdb::NmrOneD 330481 Specdb::MsMs 29489 Specdb::MsMs 29490 Specdb::MsMs 29491 Specdb::MsMs 36047 Specdb::MsMs 36048 Specdb::MsMs 36049 HMDB12277 1012 987 C04896 PHOSPHORIBOSYL-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 Histidine biosynthesis bifunctional protein hisIE P06989 HIS2_ECOLI hisI http://ecmdb.ca/proteins/P06989.xml 1-(5-phosphoribosyl)-5-[(5-phosphoribosylamino)methylideneamino] imidazole-4-carboxamide isomerase P10371 HIS4_ECOLI hisA http://ecmdb.ca/proteins/P10371.xml PhosphoribosylformiminoAICAR-phosphate <> Phosphoribulosylformimino-AICAR-P R04640 PRIBFAICARPISOM-RXN Water + Phosphoribosyl-AMP <> PhosphoribosylformiminoAICAR-phosphate R04037 HISTCYCLOHYD-RXN Phosphoribosyl-AMP + Water > PhosphoribosylformiminoAICAR-phosphate R04037 HISTCYCLOHYD-RXN PhosphoribosylformiminoAICAR-phosphate > Phosphoribulosylformimino-AICAR-P R04640 PRIBFAICARPISOM-RXN AICAR > PhosphoribosylformiminoAICAR-phosphate PW_R002868 Water + Phosphoribosyl-AMP <> PhosphoribosylformiminoAICAR-phosphate PhosphoribosylformiminoAICAR-phosphate <> Phosphoribulosylformimino-AICAR-P