2.0 2012-05-31 14:08:27 -0600 2015-06-03 15:54:52 -0600 ECMDB06456 M2MDB000672 N-Acetyl-L-glutamyl 5-phosphate N-Acetyl-L-glutamyl 5-phosphate is an intermediate in urea cycle and metabolism of amino groups. The enzyme N-acetyl-gamma-glutamyl-phosphate reductase [EC:1.2.1.38] catalyzes the conversion of this metabolite into N-acetyl-L-glutamate 5-semialdehyde. This reaction is irreversible and occurs in the cytoplasm (BiGG database) (2S)-2-acetamido-5-oxo-5-(phosphonooxy)pentanoate (2S)-2-acetamido-5-oxo-5-(phosphonooxy)pentanoic acid N-acetyl-5-glutamyl phosphate N-acetyl-glutamyl-P N-acetyl-L-glutamate-5-phosphate N-acetylglutamyl-P N-Acetyl-5-glutamyl phosphate n-Acetyl-5-glutamyl phosphoric acid N-Acetyl-5-glutamyl phosphoric acid N-Acetyl-5-oxo-5-(phosphonooxy)-L-norvaline N-Acetyl-g-L-glutamyl phosphate N-Acetyl-g-L-glutamyl phosphoric acid N-Acetyl-gamma-L-glutamyl phosphate N-Acetyl-gamma-L-glutamyl phosphoric acid N-Acetyl-glutamyl-P N-Acetyl-L-glutamate 5-phosphate N-Acetyl-L-glutamate-5-phosphate N-Acetyl-L-glutamic acid 5-phosphate N-Acetyl-L-glutamic acid 5-phosphoric acid n-Acetyl-L-glutamic acid-5-phosphoric acid N-Acetyl-L-glutamic acid-5-phosphoric acid N-Acetyl-L-glutamyl 5-phosphate N-Acetyl-L-glutamyl 5-phosphoric acid N-Acetyl-γ-L-glutamyl phosphate N-Acetyl-γ-L-glutamyl phosphoric acid N-Acetylglutamyl-P N-AcGlu-P C7H12NO8P 269.1458 269.030052877 (2S)-2-acetamido-5-oxo-5-(phosphonooxy)pentanoic acid (2S)-2-acetamido-5-oxo-5-(phosphonooxy)pentanoic acid 15383-57-0 CC(=O)N[C@@H](CCC(=O)OP(O)(O)=O)C(O)=O InChI=1S/C7H12NO8P/c1-4(9)8-5(7(11)12)2-3-6(10)16-17(13,14)15/h5H,2-3H2,1H3,(H,8,9)(H,11,12)(H2,13,14,15)/t5-/m0/s1 FCVIHFVSXHOPSW-YFKPBYRVSA-N Solid Cytosol logp -1.92 ALOGPS logs -1.87 ALOGPS solubility 3.64e+00 g/l ALOGPS logp -1.8 ChemAxon pka_strongest_acidic 1.23 ChemAxon pka_strongest_basic -1.8 ChemAxon iupac (2S)-2-acetamido-5-oxo-5-(phosphonooxy)pentanoic acid ChemAxon average_mass 269.1458 ChemAxon mono_mass 269.030052877 ChemAxon smiles CC(=O)N[C@@H](CCC(=O)OP(O)(O)=O)C(O)=O ChemAxon formula C7H12NO8P ChemAxon inchi InChI=1S/C7H12NO8P/c1-4(9)8-5(7(11)12)2-3-6(10)16-17(13,14)15/h5H,2-3H2,1H3,(H,8,9)(H,11,12)(H2,13,14,15)/t5-/m0/s1 ChemAxon inchikey FCVIHFVSXHOPSW-YFKPBYRVSA-N ChemAxon polar_surface_area 150.23 ChemAxon refractivity 51.89 ChemAxon polarizability 21.95 ChemAxon rotatable_bond_count 7 ChemAxon acceptor_count 7 ChemAxon donor_count 4 ChemAxon physiological_charge -3 ChemAxon formal_charge 0 ChemAxon Arginine and proline metabolism ec00330 Metabolic pathways eco01100 arginine metabolism The metabolism of L-arginine starts with the acetylation of L-glutamic acid resulting in a N-acetylglutamic acid while releasing a coenzyme A and a hydrogen ion. N-acetylglutamic acid is then phosphorylated via an ATP driven acetylglutamate kinase which yields a N-acetyl-L-glutamyl 5-phosphate. This compound undergoes a NDPH dependent reduction resulting in N-acetyl-L-glutamate 5-semialdehyde. This compound reacts with L-glutamic acid through a acetylornithine aminotransferase / N-succinyldiaminopimelate aminotransferase to produce a N-acetylornithine which is then deacetylated through a acetylornithine deacetylase which yield an ornithine. L-glutamine is used to synthesize carbamoyl phosphate through the interaction of L-glutamine, water, ATP, and hydrogen carbonate. This reaction yields ADP, L-glutamic acid, phosphate, and hydrogen ion. Carbamoyl phosphate and ornithine are used to catalyze the production of citrulline through an ornithine carbamoyltransferase. Citrulline reacts with L-aspartic acid through an ATP dependent enzyme, argininosuccinate synthase to produce pyrophosphate, AMP and argininosuccinic acid. Argininosussinic acid is then lyase to produce L-arginine and fumaric acid. L-arginine can be metabolized into succinic acid by two different sets of reactions: 1. Arginine reacts with succinyl-CoA through a arginine N-succinyltransferase resulting in N2-succinyl-L-arginine while releasing CoA and Hydrogen Ion. N2-succinyl-L-arginine is then dihydrolase to produce a N2-succinyl-L-ornithine through a N-succinylarginine dihydrolase. This compound in turn reacts with oxoglutaric acid through succinylornithine transaminase resulting in L-glutamic acid and N2-succinyl-L-glutamic acid 5-semialdehyde. This compoud in turn reacts with a NAD dependent dehydrogenase resulting in N2-succinylglutamate while releasing NADH and hydrogen ion. N2-succinylglutamate reacts with water through a succinylglutamate desuccinylase resulting in L-glutamic acid and a succinic acid. The succinic acid is then incorporated in the TCA cycle 2.Argine reacts with carbon dioxide and a hydrogen ion through a biodegradative arginine decarboxylase, resulting in Agmatine. This compound is then transformed into putrescine by reacting with water and an agmatinase, and releasing urea. Putrescine can be metabolized by reaction with either l-glutamic acid or oxoglutaric acid. If putrescine reacts with L-glutamic acid, it reacts through an ATP mediated gamma-glutamylputrescine producing a hydrogen ion, ADP, phosphate and gamma-glutamyl-L-putrescine. This compound is reduced by interacting with oxygen, water and a gamma-glutamylputrescine oxidoreductase resulting in ammonium, hydrogen peroxide and 4-gamma-glutamylamino butanal. This compound is dehydrogenated through a NADP mediated reaction lead by gamma-glutamyl-gamma-aminobutaryaldehyde dehydrogenase resulting in hydrogen ion, NADPH and 4-glutamylamino butanoate. In turn, the latter compound reacts with water through a gamma-glutamyl-gamma-aminobutyrate hydrolase resulting in L-glutamic acid and Gamma aminobutyric acid. On the other hand, if putrescine reacts with oxoglutaric acid through a putrescine aminotransferase, it results in L-glutamic acid, and a 4-aminobutyraldehyde. This compound reacts with water through a NAD dependent gamma aminobutyraldehyde dehydrogenase resulting in hydrogen ion, NADH and gamma-aminobutyric acid. Gamma Aaminobutyric acid reacts with oxoglutaric acid through 4-aminobutyrate aminotransferase resulting in L-glutamic acid and succinic acid semialdehyde. This compound in turn can react with with either NADP or NAD to result in the production of succinic acid through succinate-semialdehyde dehydrogenase or aldehyde dehydrogenase-like protein yneI respectively. Succinic acid can then be integrated in the TCA cycle. L-arginine is eventua lly metabolized into succinic acid which then goes to the TCA cycle PW000790 Metabolic ornithine metabolism In the ornithine biosynthesis pathway of E. coli, L-glutamate is acetylated to N-acetylglutamate by the enzyme N-acetylglutamate synthase, encoded by the argA gene. The acetyl donor for this reaction is acetyl-CoA. N-acetylglutamic acid is then phosphorylated via an ATP driven acetylglutamate kinase which yields a N-acetyl-L-glutamyl 5-phosphate. This compound undergoes a NADPH dependent reduction resulting in N-acetyl-L-glutamate 5-semialdehyde. This compound reacts with L-glutamic acid through a acetylornithine aminotransferase / N-succinyldiaminopimelate aminotransferase to produce a N-acetylornithine which is then deacetylated through a acetylornithine deacetylase which yield an ornithine. Ornithine interacts with hydrogen ion through a Ornithine decarboxylase resulting in a carbon dioxide release and a putrescine Putrescine can be metabolized by reaction with either l-glutamic acid or oxoglutaric acid. If putrescine reacts with L-glutamic acid, it reacts through an ATP mediated gamma-glutamylputrescine producing a hydrogen ion, ADP, phosphate and gamma-glutamyl-L-putrescine. This compound is reduced by interacting with oxygen, water and a gamma-glutamylputrescine oxidoreductase resulting in ammonium, hydrogen peroxide and 4-gamma-glutamylamino butanal. This compound is dehydrogenated through a NADP mediated reaction lead by gamma-glutamyl-gamma-aminobutaryaldehyde dehydrogenase resulting in hydrogen ion, NADPH and 4-glutamylamino butanoate. In turn, the latter compound reacts with water through a gamma-glutamyl-gamma-aminobutyrate hydrolase resulting in L-glutamic acid and Gamma aminobutyric acid. On the other hand, if putrescine reacts with oxoglutaric acid through a putrescine aminotransferase, it results in L-glutamic acid, and a 4-aminobutyraldehyde. This compound reacts with water through a NAD dependent gamma aminobutyraldehyde dehydrogenase resulting in hydrogen ion, NADH and gamma-aminobutyric acid. Gamma Aaminobutyric acid reacts with oxoglutaric acid through 4-aminobutyrate aminotransferase resulting in L-glutamic acid and succinic acid semialdehyde. This compound in turn can react with with either NADP or NAD to result in the production of succinic acid through succinate-semialdehyde dehydrogenase or aldehyde dehydrogenase-like protein yneI respectively. Succinic acid can then be integrated in the TCA cycle. PW000791 Metabolic ornithine biosynthesis GLUTORN-PWY Specdb::CMs 2853 Specdb::CMs 39016 Specdb::CMs 162302 Specdb::NmrOneD 150180 Specdb::NmrOneD 150181 Specdb::NmrOneD 150182 Specdb::NmrOneD 150183 Specdb::NmrOneD 150184 Specdb::NmrOneD 150185 Specdb::NmrOneD 150186 Specdb::NmrOneD 150187 Specdb::NmrOneD 150188 Specdb::NmrOneD 150189 Specdb::NmrOneD 150190 Specdb::NmrOneD 150191 Specdb::NmrOneD 150192 Specdb::NmrOneD 150193 Specdb::NmrOneD 150194 Specdb::NmrOneD 150195 Specdb::NmrOneD 150196 Specdb::NmrOneD 150197 Specdb::NmrOneD 150198 Specdb::NmrOneD 150199 Specdb::MsMs 31697 Specdb::MsMs 31698 Specdb::MsMs 31699 Specdb::MsMs 2422548 Specdb::MsMs 2422549 Specdb::MsMs 2422550 Specdb::MsMs 25139 Specdb::MsMs 25140 Specdb::MsMs 25141 Specdb::MsMs 2512614 Specdb::MsMs 2512615 Specdb::MsMs 2512616 HMDB06456 440236 389220 C04133 16878 N-ACETYL-GLUTAMYL-P X2W 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 Kuramitsu, Shigenori; Masui, Ryoji. Cloning of thermostable acetylglutamate kinase gene from Sulfolobus tokodaii and use for N-acetyl-L-glutamate-5-phosphate biosynthesis. Jpn. Kokai Tokkyo Koho (2004), 12 pp. CODEN: JKXXAF JP 2004298187 A 2 Acetylglutamate kinase P0A6C8 ARGB_ECOLI argB http://ecmdb.ca/proteins/P0A6C8.xml N-acetyl-gamma-glutamyl-phosphate reductase P11446 ARGC_ECOLI argC http://ecmdb.ca/proteins/P11446.xml N-Acetyl-L-glutamate 5-semialdehyde + NADP + Phosphate <> N-Acetyl-L-glutamyl 5-phosphate + Hydrogen ion + NADPH R03443 N-ACETYLGLUTPREDUCT-RXN N-Acetyl-L-alanine + Adenosine triphosphate + N-Acetylglutamic acid <> N-Acetyl-L-glutamyl 5-phosphate + ADP R02649 Adenosine triphosphate + N-Acetyl-L-alanine <> ADP + N-Acetyl-L-glutamyl 5-phosphate R02649 N-acetyl-L-glutamate + Adenosine triphosphate > N-Acetyl-L-glutamyl 5-phosphate + ADP ACETYLGLUTKIN-RXN Adenosine triphosphate + N-acetyl-L-glutamate > ADP + N-Acetyl-L-glutamyl 5-phosphate N-Acetyl-L-glutamate 5-semialdehyde + NADP + Inorganic phosphate > N-Acetyl-L-glutamyl 5-phosphate + NADPH N-Acetylglutamic acid + Adenosine triphosphate + N-Acetylglutamic acid > Adenosine diphosphate + N-Acetyl-L-glutamyl 5-phosphate + ADP PW_R002671 N-Acetyl-L-glutamyl 5-phosphate + NADPH + Hydrogen ion + NADPH > N-acetyl-L-glutamate + Phosphate + NADP PW_R002672 N-Acetyl-L-glutamate 5-semialdehyde + NADP + Phosphate <> N-Acetyl-L-glutamyl 5-phosphate + Hydrogen ion + NADPH N-Acetyl-L-alanine + Adenosine triphosphate + N-Acetylglutamic acid <> N-Acetyl-L-glutamyl 5-phosphate + ADP