2.0 2012-08-09 09:16:13 -0600 2015-09-13 15:15:33 -0600 ECMDB21429 M2MDB001824 N-Acetylglutamic acid N-acetylglutamic acid is an acetylated amino acid. It is involved in arginine biosynthesis and is a substrate for both ArgA and ArgB in E. coli. 2-acetamido-L-Glutaraldehydate 2-acetamido-L-Glutaraldehydic acid Ac-Glu-OH Acetyl-glutamate Acetyl-glutamic acid Acetyl-L-glutamate Acetyl-L-glutamic acid Acetylglutamate Acetylglutamic acid DL-Acetylglutamate DL-Acetylglutamic acid N-Ac-Glu-OH N-acetyl L-glutamate N-acetyl L-glutamic acid N-Acetyl-DL-glutamate N-Acetyl-DL-glutamic acid N-acetyl-Glutamate N-acetyl-Glutamic acid N-Acetyl-L-glutamate N-Acetyl-L-glutamate-g-semialdehyde N-Acetyl-L-glutamate-gamma-semialdehyde N-Acetyl-L-glutamate-γ-semialdehyde N-Acetyl-L-glutamic acid N-Acetyl-L-glutamic acid-g-semialdehyde N-Acetyl-L-glutamic acid-gamma-semialdehyde N-Acetyl-L-glutamic acid-γ-semialdehyde N-Acetylglutamate N-Acetylglutamic g-semialdehyde N-Acetylglutamic gamma-semialdehyde N-Acetylglutamic γ-semialdehyde N-AcGlu C7H11NO5 189.1659 189.063722467 (2S)-2-acetamidopentanedioic acid N-acetyl-L-glutamate 1188-37-0 CC(=O)NC(CCC(O)=O)C(O)=O InChI=1S/C7H11NO5/c1-4(9)8-5(7(12)13)2-3-6(10)11/h5H,2-3H2,1H3,(H,8,9)(H,10,11)(H,12,13) RFMMMVDNIPUKGG-UHFFFAOYSA-N Solid Cytoplasm logp -0.67 ALOGPS logs -1.01 ALOGPS solubility 1.86e+01 g/l ALOGPS melting_point 199 - 201 oC logp -1.1 ChemAxon pka_strongest_acidic 3.43 ChemAxon pka_strongest_basic -1.8 ChemAxon iupac (2S)-2-acetamidopentanedioic acid ChemAxon average_mass 189.1659 ChemAxon mono_mass 189.063722467 ChemAxon smiles CC(=O)NC(CCC(O)=O)C(O)=O ChemAxon formula C7H11NO5 ChemAxon inchi InChI=1S/C7H11NO5/c1-4(9)8-5(7(12)13)2-3-6(10)11/h5H,2-3H2,1H3,(H,8,9)(H,10,11)(H,12,13) ChemAxon inchikey RFMMMVDNIPUKGG-UHFFFAOYSA-N ChemAxon polar_surface_area 103.7 ChemAxon refractivity 40.73 ChemAxon polarizability 17.44 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 5 ChemAxon donor_count 3 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon Arginine and proline metabolism ec00330 Metabolic pathways eco01100 L-glutamate metabolism II PW001886 Metabolic 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 Specdb::CMs 1432 Specdb::CMs 1433 Specdb::CMs 2636 Specdb::CMs 30636 Specdb::CMs 30637 Specdb::CMs 31710 Specdb::CMs 31711 Specdb::CMs 31712 Specdb::CMs 135578 Specdb::CMs 143312 Specdb::NmrOneD 4750 Specdb::NmrOneD 4751 Specdb::NmrOneD 146590 Specdb::NmrOneD 146591 Specdb::NmrOneD 146592 Specdb::NmrOneD 146593 Specdb::NmrOneD 146594 Specdb::NmrOneD 146595 Specdb::NmrOneD 146596 Specdb::NmrOneD 146597 Specdb::NmrOneD 146598 Specdb::NmrOneD 146599 Specdb::NmrOneD 146600 Specdb::NmrOneD 146601 Specdb::NmrOneD 146602 Specdb::NmrOneD 146603 Specdb::NmrOneD 146604 Specdb::NmrOneD 146605 Specdb::NmrOneD 146606 Specdb::NmrOneD 146607 Specdb::NmrOneD 146608 Specdb::NmrOneD 146609 Specdb::MsMs 46128 Specdb::MsMs 46129 Specdb::MsMs 46130 Specdb::MsMs 146340 Specdb::MsMs 146341 Specdb::MsMs 146342 Specdb::MsMs 437122 Specdb::MsMs 437123 Specdb::MsMs 437124 Specdb::MsMs 437125 Specdb::MsMs 437126 Specdb::MsMs 440105 Specdb::MsMs 445551 Specdb::MsMs 445552 Specdb::MsMs 445553 Specdb::MsMs 445554 Specdb::MsMs 445555 Specdb::MsMs 451941 Specdb::MsMs 2236646 Specdb::MsMs 2236742 Specdb::MsMs 2238767 Specdb::MsMs 2238802 Specdb::MsMs 2240784 Specdb::MsMs 2240927 Specdb::MsMs 2242807 Specdb::NmrTwoD 2036 HMDB01138 185 180 C00624 12575 N-Acetylglutamic acid 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 Yurtsever D. (2007). Fatty acid methyl ester profiling of Enterococcus and Esherichia coli for microbial source tracking. M.sc. Thesis. Villanova University: U.S.A Sugahara K, Zhang J, Kodama H: Liquid chromatographic-mass spectrometric analysis of N-acetylamino acids in human urine. J Chromatogr B Biomed Appl. 1994 Jul 1;657(1):15-21. 7952062 Zhang W, Holzknecht RA, Butkowski RJ, Tuchman M: Immunochemical analysis of carbamyl phosphate synthetase I and ornithine transcarbamylase deficient livers: elevated N-acetylglutamate level in a liver lacking carbamyl phosphate synthetase protein. Clin Invest Med. 1990 Aug;13(4):183-8. 2208834 Tavazzi B, Lazzarino G, Leone P, Amorini AM, Bellia F, Janson CG, Di Pietro V, Ceccarelli L, Donzelli S, Francis JS, Giardina B: Simultaneous high performance liquid chromatographic separation of purines, pyrimidines, N-acetylated amino acids, and dicarboxylic acids for the chemical diagnosis of inborn errors of metabolism. Clin Biochem. 2005 Nov;38(11):997-1008. Epub 2005 Sep 1. 16139832 Tuchman M, Holzknecht RA: N-acetylglutamate content in liver and gut of normal and fasted mice, normal human livers, and livers of individuals with carbamyl phosphate synthetase or ornithine transcarbamylase deficiency. Pediatr Res. 1990 Apr;27(4 Pt 1):408-12. 2342831 Vockley J, Vockley CM, Lin SP, Tuchman M, Wu TC, Lin CY, Seashore MR: Normal N-acetylglutamate concentration measured in liver from a new patient with N-acetylglutamate synthetase deficiency: physiologic and biochemical implications. Biochem Med Metab Biol. 1992 Feb;47(1):38-46. 1562355 hang, Xiaolin; Yang, Qiyong; Sun, Yuesheng. Preparation of N-acetyl-L-glutamic acid. Huaxue Shijie (2002), 43(7), 363-365. http://hmdb.ca/system/metabolites/msds/000/001/023/original/HMDB01138.pdf?1358463345 Amino-acid acetyltransferase P0A6C5 ARGA_ECOLI argA http://ecmdb.ca/proteins/P0A6C5.xml Acetylglutamate kinase P0A6C8 ARGB_ECOLI argB http://ecmdb.ca/proteins/P0A6C8.xml N-Acetyl-L-alanine + Adenosine triphosphate + N-Acetylglutamic acid <> N-Acetyl-L-glutamyl 5-phosphate + ADP R02649 Acetyl-CoA + L-Glutamate <> N-Acetyl-L-alanine + Coenzyme A + Hydrogen ion + N-Acetylglutamic acid R00259 L-Glutamic acid + Acetyl-CoA + L-Glutamate > Coenzyme A + Hydrogen ion + N-Acetylglutamic acid + N-Acetylglutamic acid PW_R002670 N-Acetylglutamic acid + Adenosine triphosphate + N-Acetylglutamic acid > Adenosine diphosphate + N-Acetyl-L-glutamyl 5-phosphate + ADP PW_R002671 Acetyl-CoA + L-Glutamic acid + L-Glutamate <> N-Acetyl-L-alanine + Coenzyme A + Hydrogen ion + N-Acetylglutamic acid + N-Acetyl-L-alanine + N-Acetylglutamic acid PW_R005149 Acetyl-CoA + L-Glutamate <> N-Acetyl-L-alanine + Coenzyme A + Hydrogen ion + N-Acetylglutamic acid N-Acetyl-L-alanine + Adenosine triphosphate + N-Acetylglutamic acid <> N-Acetyl-L-glutamyl 5-phosphate + ADP