2.0 2012-05-31 14:27:23 -0600 2015-06-03 17:19:18 -0600 ECMDB20098 M2MDB000946 5-Amino-4-imidazolecarboxyamide 5-Amino-4-imidazolecarboxyamide is a metabolite of purine metabolism. Adenine phosphoribosyltransferase [EC:2.4.2.7] catalyzes both the formation of 5-Amino-4-imidazolecarboxyamide and its conversion to 1-(5'-Phosphoribosyl)-5-amino-4-imidazolecarboxamide, also called AICAR. (KEGG) 1H-Imidazole-4-carboxamide, 5-amino-, monohydrochloride 360-97-4 (FREE BASE) 4-Amino-1H-imidazole-5-carboxamide 4-Amino-5-carboxamido imidazole hydrochloride 4-Amino-5-imidazole carboxamide 4-Amino-5-Imidazolecarboxamide 4-Amino-5-imidazolecarboxamide hydrochloride 4-Aminoimidazole-5-carboxamide 4-Aminoimidazole-5-carboxamide hydrochoride 4-Carbamoyl-5-aminoimidazole 4-Carboxamido-5-aminoimidazole 5'-P-Ribosyl-5-amino-4-imidazole carboxamide 5'-Phosphoribosyl-5-amino-4-imidazole carboxamide 5(OR 4)-AMINO-IMIDAZOLE-4(OR 5)-CARBOXAMIDE 5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamide 5-Amino-1H-Imidazole-4-carboxamide 5-Amino-4-imidazolecarboxamide 5-Amino-4-imidazolecarboxamide ribotide 5-Amino-Imidazole-4-carboxamide 5-Aminoimidazol-4-carboxamide 5-Aminoimidazol-4-carboxamide, hydrochloride 5-Aminoimidazole carboxamide 5-Aminoimidazole-4-carboxamide 5-Aminoimidazole-4-carboxamide hydrochloride 5-Aminoimidazole-4-carboxamide ribotide 5-Aminoimidazolecarboxamide 5-Imidazolecarboxamide, 4-amino-, hydrochloride AIC Aic .cntdot. HCL AICA AICA ribonucleotide Aicar Aminoimidazole carboxamide Colahepat Diazol-c Imidazole C-4,5 deriv. 2 Imidazole-4-carboxamide, 5-amino-, monohydrochloride WLN: T5M CNJ DVZ EZ Z-Nucleotide C4H6N4O 126.1166 126.054160834 4-amino-1H-imidazole-5-carboxamide 4-aminoimidazole-5-carboxamide 72-40-2 NC(=O)C1=C(N)N=CN1 InChI=1S/C4H6N4O/c5-3-2(4(6)9)7-1-8-3/h1H,5H2,(H2,6,9)(H,7,8) DVNYTAVYBRSTGK-UHFFFAOYSA-N Solid Cytoplasm Periplasm logp -1.16 ALOGPS logs -0.01 ALOGPS solubility 1.24e+02 g/l ALOGPS logp -0.96 ChemAxon pka_strongest_acidic 12.74 ChemAxon pka_strongest_basic 5.26 ChemAxon iupac 4-amino-1H-imidazole-5-carboxamide ChemAxon average_mass 126.1166 ChemAxon mono_mass 126.054160834 ChemAxon smiles NC(=O)C1=C(N)N=CN1 ChemAxon formula C4H6N4O ChemAxon inchi InChI=1S/C4H6N4O/c5-3-2(4(6)9)7-1-8-3/h1H,5H2,(H2,6,9)(H,7,8) ChemAxon inchikey DVNYTAVYBRSTGK-UHFFFAOYSA-N ChemAxon polar_surface_area 97.79 ChemAxon refractivity 32.98 ChemAxon polarizability 11.37 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 3 ChemAxon donor_count 3 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Purine metabolism ec00230 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 inosine-5'-phosphate biosynthesis I PWY-6123 Specdb::CMs 1440 Specdb::CMs 1451 Specdb::CMs 25213 Specdb::CMs 31444 Specdb::CMs 31445 Specdb::CMs 31725 Specdb::CMs 31726 Specdb::CMs 31790 Specdb::CMs 160991 Specdb::NmrOneD 135320 Specdb::NmrOneD 135321 Specdb::NmrOneD 135322 Specdb::NmrOneD 135323 Specdb::NmrOneD 135324 Specdb::NmrOneD 135325 Specdb::NmrOneD 135326 Specdb::NmrOneD 135327 Specdb::NmrOneD 135328 Specdb::NmrOneD 135329 Specdb::NmrOneD 135330 Specdb::NmrOneD 135331 Specdb::NmrOneD 135332 Specdb::NmrOneD 135333 Specdb::NmrOneD 135334 Specdb::NmrOneD 135335 Specdb::NmrOneD 135336 Specdb::NmrOneD 135337 Specdb::NmrOneD 135338 Specdb::NmrOneD 135339 Specdb::MsMs 23192 Specdb::MsMs 23193 Specdb::MsMs 23194 Specdb::MsMs 29990 Specdb::MsMs 29991 Specdb::MsMs 29992 Specdb::MsMs 437244 Specdb::MsMs 437245 Specdb::MsMs 437246 Specdb::MsMs 437247 Specdb::MsMs 437248 Specdb::MsMs 445716 Specdb::MsMs 445717 Specdb::MsMs 445718 Specdb::MsMs 445719 Specdb::MsMs 445720 Specdb::MsMs 2239673 Specdb::MsMs 3055352 Specdb::MsMs 3055353 Specdb::MsMs 3055354 Specdb::MsMs 3111614 Specdb::MsMs 3111615 Specdb::MsMs 3111616 9679 9298 C04051 18406 AICAR 5AC 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 Adenine phosphoribosyltransferase P69503 APT_ECOLI apt http://ecmdb.ca/proteins/P69503.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 AICAR + Pyrophosphate <> 5-Amino-4-imidazolecarboxyamide + Phosphoribosyl pyrophosphate R04378 Phosphoribulosylformimino-AICAR-P + L-Glutamine > L-Glutamic acid + Hydrogen ion + 5-Amino-4-imidazolecarboxyamide + D-Erythro-imidazole-glycerol-phosphate + L-Glutamate PW_R002869