2.02012-05-31 13:03:09 -06002015-06-03 15:53:39 -0600ECMDB00999M2MDB000220Phosphoribosylformylglycineamidine5-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)acetamidine5'-phosphoribosyl-<i>N</i>-formyl glycineamidine5'-Phosphoribosyl-N-formyl glycineamidine5'-Phosphoribosylformylglycinamidine5-Phosphoribosyl-N-formylglycineamidineFGAMN-(2-Amino-2-iminoethyl)-N-(5-O-phosphono-b-D-ribofuranosyl)-FormamideN-(2-amino-2-Iminoethyl)-N-(5-O-phosphono-b-delta-ribofuranosyl)-formamideN-(2-amino-2-Iminoethyl)-N-(5-O-phosphono-b-δ-ribofuranosyl)-formamideN-(2-Amino-2-iminoethyl)-N-(5-O-phosphono-beta-delta-ribofuranosyl)-FormamideN-(2-amino-2-Iminoethyl)-N-(5-O-phosphono-β-δ-ribofuranosyl)-formamideC8H16N3O8P313.2017313.067501015{[(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 acid37721-04-3O[C@H]1[C@@H](O)[C@H](NC(=N)CNC=O)O[C@@H]1COP(O)(O)=OInChI=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/s1PMCOGCVKOAOZQM-XVFCMESISA-NSolidCytosollogp-2.58logs-1.56solubility8.65e+00 g/llogp-4.1pka_strongest_acidic1.23pka_strongest_basic7.38iupac{[(2R,3S,4R,5R)-3,4-dihydroxy-5-(2-formamidoethanimidamido)oxolan-2-yl]methoxy}phosphonic acidaverage_mass313.2017mono_mass313.067501015smilesO[C@H]1[C@@H](O)[C@H](NC(=N)CNC=O)O[C@@H]1COP(O)(O)=OformulaC8H16N3O8PinchiInChI=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/s1inchikeyPMCOGCVKOAOZQM-XVFCMESISA-Npolar_surface_area181.43refractivity72.72polarizability25.96rotatable_bond_count6acceptor_count9donor_count7physiological_charge-1formal_charge0Purine metabolismec00230Metabolic pathwayseco01100superpathway of 5-aminoimidazole ribonucleotide biosynthesisPWY-62775-aminoimidazole ribonucleotide biosynthesis IPWY-61215-aminoimidazole ribonucleotide biosynthesis IIPWY-6122Specdb::CMs13440Specdb::CMs37884Specdb::CMs133579Specdb::CMs141313Specdb::NmrOneD116118Specdb::NmrOneD116119Specdb::NmrOneD116120Specdb::NmrOneD116121Specdb::NmrOneD116122Specdb::NmrOneD116123Specdb::NmrOneD116124Specdb::NmrOneD116125Specdb::NmrOneD116126Specdb::NmrOneD116127Specdb::NmrOneD116128Specdb::NmrOneD116129Specdb::NmrOneD116130Specdb::NmrOneD116131Specdb::NmrOneD116132Specdb::NmrOneD116133Specdb::NmrOneD116134Specdb::NmrOneD116135Specdb::NmrOneD116136Specdb::NmrOneD116137Specdb::MsMs26147Specdb::MsMs26148Specdb::MsMs26149Specdb::MsMs32705Specdb::MsMs32706Specdb::MsMs32707Specdb::MsMs2715988Specdb::MsMs2715989Specdb::MsMs2715990Specdb::MsMs2962134Specdb::MsMs2962135Specdb::MsMs2962136HMDB009991547830994C04640184135-PHOSPHORIBOSYL-N-FORMYLGLYCINEAMIDINEKeseler, 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 370:17-25.17765195Winder, 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 80:2939-2948.18331064Jayaram 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):88-92.2347042Maegawa 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):34-41.11800470Phosphoribosylformylglycinamidine cyclo-ligaseP08178PUR5_ECOLIpurMhttp://ecmdb.ca/proteins/P08178.xmlPhosphoribosylformylglycinamidine synthaseP15254PUR4_ECOLIpurLhttp://ecmdb.ca/proteins/P15254.xmlAdenosine triphosphate + Phosphoribosylformylglycineamidine <> ADP + 5-Aminoimidazole ribonucleotide +2 Hydrogen ion + PhosphateR04208AIRS-RXNAdenosine triphosphate + 5'-Phosphoribosyl-N-formylglycineamide + L-Glutamine + Water <> ADP + Phosphoribosylformylglycineamidine + L-Glutamate + Hydrogen ion + PhosphateR04463FGAMSYN-RXNAdenosine triphosphate + Phosphoribosylformylglycineamidine <> ADP + Phosphate + 5-Aminoimidazole ribonucleotideR04208Adenosine triphosphate + 5'-Phosphoribosyl-N-formylglycineamide + L-Glutamine + Water <> ADP + Phosphate + Phosphoribosylformylglycineamidine + L-GlutamateR04463FGAMSYN-RXNAdenosine triphosphate + Phosphoribosylformylglycineamidine > Hydrogen ion + ADP + Phosphate + 5-Aminoimidazole ribonucleotideR04208AIRS-RXNAdenosine triphosphate + 5'-Phosphoribosyl-N-formylglycineamide + L-Glutamine + Water > Hydrogen ion + ADP + Phosphate + Phosphoribosylformylglycineamidine + L-GlutamateFGAMSYN-RXNAdenosine triphosphate + Phosphoribosylformylglycineamidine <> ADP +5 5-Aminoimidazole ribonucleotide +2 Hydrogen ion + PhosphateAdenosine triphosphate + 5 5'-Phosphoribosyl-N-formylglycineamide + L-Glutamine + Water <> ADP + Phosphoribosylformylglycineamidine + L-Glutamate + Hydrogen ion + PhosphateAdenosine triphosphate + 5 5'-Phosphoribosyl-N-formylglycineamide + L-Glutamine + Water <> ADP + Phosphoribosylformylglycineamidine + L-Glutamate + Hydrogen ion + Phosphate