2.0 2012-05-31 13:03:09 -0600 2015-06-03 15:53:39 -0600 ECMDB00999 M2MDB000220 Phosphoribosylformylglycineamidine 5-Phosphoribosyl-n-formylglycineamidine is part of the 5-aminoimidazole ribonucleotide biosynthesis pathway. 5-amino-1-(5-phospho-D-ribosyl)imidazole (AIR) is a key intermediate in the biosynthesis of purine nocleotides and thiamine. It is synthesized from 5-phospho-alpha-D-ribose 1-diphosphate (PRPP) in 5 steps, catalyzed by the enzymes amidophosphoribosyl transferase, phosphoribosylamine-glycine ligase, phosphoribosylglycinamide formyltransferase, phosphoribosylformylglycinamide synthetase and phosphoribosylformylglycinamide cyclo-ligase. 2-(Formamido)-N1-(5-phospho-D-ribosyl)acetamidine 5'-phosphoribosyl-<i>N</i>-formyl glycineamidine 5'-Phosphoribosyl-N-formyl glycineamidine 5'-Phosphoribosylformylglycinamidine 5-Phosphoribosyl-N-formylglycineamidine FGAM N-(2-Amino-2-iminoethyl)-N-(5-O-phosphono-b-D-ribofuranosyl)-Formamide N-(2-amino-2-Iminoethyl)-N-(5-O-phosphono-b-delta-ribofuranosyl)-formamide N-(2-amino-2-Iminoethyl)-N-(5-O-phosphono-b-δ-ribofuranosyl)-formamide N-(2-Amino-2-iminoethyl)-N-(5-O-phosphono-beta-delta-ribofuranosyl)-Formamide N-(2-amino-2-Iminoethyl)-N-(5-O-phosphono-β-δ-ribofuranosyl)-formamide C8H16N3O8P 313.2017 313.067501015 {[(2R,3S,4R,5R)-3,4-dihydroxy-5-(2-formamidoethanimidamido)oxolan-2-yl]methoxy}phosphonic acid [(2R,3S,4R,5R)-3,4-dihydroxy-5-(2-formamidoethanimidamido)oxolan-2-yl]methoxyphosphonic acid 37721-04-3 O[C@H]1[C@@H](O)[C@H](NC(=N)CNC=O)O[C@@H]1COP(O)(O)=O InChI=1S/C8H16N3O8P/c9-5(1-10-3-12)11-8-7(14)6(13)4(19-8)2-18-20(15,16)17/h3-4,6-8,13-14H,1-2H2,(H2,9,11)(H,10,12)(H2,15,16,17)/t4-,6-,7-,8-/m1/s1 PMCOGCVKOAOZQM-XVFCMESISA-N Solid Cytosol logp -2.58 ALOGPS logs -1.56 ALOGPS solubility 8.65e+00 g/l ALOGPS logp -4.1 ChemAxon pka_strongest_acidic 1.23 ChemAxon pka_strongest_basic 7.38 ChemAxon iupac {[(2R,3S,4R,5R)-3,4-dihydroxy-5-(2-formamidoethanimidamido)oxolan-2-yl]methoxy}phosphonic acid ChemAxon average_mass 313.2017 ChemAxon mono_mass 313.067501015 ChemAxon smiles O[C@H]1[C@@H](O)[C@H](NC(=N)CNC=O)O[C@@H]1COP(O)(O)=O ChemAxon formula C8H16N3O8P ChemAxon inchi InChI=1S/C8H16N3O8P/c9-5(1-10-3-12)11-8-7(14)6(13)4(19-8)2-18-20(15,16)17/h3-4,6-8,13-14H,1-2H2,(H2,9,11)(H,10,12)(H2,15,16,17)/t4-,6-,7-,8-/m1/s1 ChemAxon inchikey PMCOGCVKOAOZQM-XVFCMESISA-N ChemAxon polar_surface_area 181.43 ChemAxon refractivity 72.72 ChemAxon polarizability 25.96 ChemAxon rotatable_bond_count 6 ChemAxon acceptor_count 9 ChemAxon donor_count 7 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Purine metabolism ec00230 Metabolic pathways eco01100 superpathway of 5-aminoimidazole ribonucleotide biosynthesis PWY-6277 5-aminoimidazole ribonucleotide biosynthesis I PWY-6121 5-aminoimidazole ribonucleotide biosynthesis II PWY-6122 Specdb::CMs 13440 Specdb::CMs 37884 Specdb::CMs 133579 Specdb::CMs 141313 Specdb::NmrOneD 116118 Specdb::NmrOneD 116119 Specdb::NmrOneD 116120 Specdb::NmrOneD 116121 Specdb::NmrOneD 116122 Specdb::NmrOneD 116123 Specdb::NmrOneD 116124 Specdb::NmrOneD 116125 Specdb::NmrOneD 116126 Specdb::NmrOneD 116127 Specdb::NmrOneD 116128 Specdb::NmrOneD 116129 Specdb::NmrOneD 116130 Specdb::NmrOneD 116131 Specdb::NmrOneD 116132 Specdb::NmrOneD 116133 Specdb::NmrOneD 116134 Specdb::NmrOneD 116135 Specdb::NmrOneD 116136 Specdb::NmrOneD 116137 Specdb::MsMs 26147 Specdb::MsMs 26148 Specdb::MsMs 26149 Specdb::MsMs 32705 Specdb::MsMs 32706 Specdb::MsMs 32707 Specdb::MsMs 2715988 Specdb::MsMs 2715989 Specdb::MsMs 2715990 Specdb::MsMs 2962134 Specdb::MsMs 2962135 Specdb::MsMs 2962136 HMDB00999 154 7830994 C04640 18413 5-PHOSPHORIBOSYL-N-FORMYLGLYCINEAMIDINE 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 Winder, 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. 18331064 Jayaram HN, Lui MS, Plowman J, Pillwein K, Reardon MA, Elliott WL, Weber G: Oncolytic activity and mechanism of action of a novel L-cysteine derivative, L-cysteine, ethyl ester, S-(N-methylcarbamate) monohydrochloride. Cancer Chemother Pharmacol. 1990;26(2):88-92. 2347042 Maegawa T, Karasawa T, Ohta T, Wang X, Kato H, Hayashi H, Nakamura S: Linkage between toxin production and purine biosynthesis in Clostridium difficile. J Med Microbiol. 2002 Jan;51(1):34-41. 11800470 Phosphoribosylformylglycinamidine cyclo-ligase P08178 PUR5_ECOLI purM http://ecmdb.ca/proteins/P08178.xml Phosphoribosylformylglycinamidine synthase P15254 PUR4_ECOLI purL http://ecmdb.ca/proteins/P15254.xml Adenosine triphosphate + Phosphoribosylformylglycineamidine <> ADP + 5-Aminoimidazole ribonucleotide +2 Hydrogen ion + Phosphate R04208 AIRS-RXN Adenosine triphosphate + 5'-Phosphoribosyl-N-formylglycineamide + L-Glutamine + Water <> ADP + Phosphoribosylformylglycineamidine + L-Glutamate + Hydrogen ion + Phosphate R04463 FGAMSYN-RXN Adenosine triphosphate + Phosphoribosylformylglycineamidine <> ADP + Phosphate + 5-Aminoimidazole ribonucleotide R04208 Adenosine triphosphate + 5'-Phosphoribosyl-N-formylglycineamide + L-Glutamine + Water <> ADP + Phosphate + Phosphoribosylformylglycineamidine + L-Glutamate R04463 FGAMSYN-RXN Adenosine triphosphate + Phosphoribosylformylglycineamidine > Hydrogen ion + ADP + Phosphate + 5-Aminoimidazole ribonucleotide R04208 AIRS-RXN Adenosine triphosphate + 5'-Phosphoribosyl-N-formylglycineamide + L-Glutamine + Water > Hydrogen ion + ADP + Phosphate + Phosphoribosylformylglycineamidine + L-Glutamate FGAMSYN-RXN Adenosine triphosphate + Phosphoribosylformylglycineamidine <> ADP +5 5-Aminoimidazole ribonucleotide +2 Hydrogen ion + Phosphate Adenosine triphosphate + 5 5'-Phosphoribosyl-N-formylglycineamide + L-Glutamine + Water <> ADP + Phosphoribosylformylglycineamidine + L-Glutamate + Hydrogen ion + Phosphate Adenosine triphosphate + 5 5'-Phosphoribosyl-N-formylglycineamide + L-Glutamine + Water <> ADP + Phosphoribosylformylglycineamidine + L-Glutamate + Hydrogen ion + Phosphate