2.0 2012-05-31 14:08:37 -0600 2015-06-03 15:54:52 -0600 ECMDB06488 M2MDB000675 N-Acetyl-L-glutamate 5-semialdehyde N-Acetyl-L-glutamate 5-semialdehyde is an intermediate in Urea cycle and metabolism of amino groups. N-Acetyl-L-glutamate 5-semialdehyde is the 2-Acetamido-5-oxopentanoate 2-Acetamido-5-oxopentanoic acid N-acetyl-L-glutamate semialdehyde N-acetyl-L-glutamate-5-semialdehyde N-acetylglutamate γ-semialdehyde N-acetylglutamate semialdehyde N-Acetyl-L-glutamate semialdehyde N-Acetyl-L-glutamate-5-semialdehyde N-Acetyl-L-glutamic acid 5-semialdehyde N-Acetyl-L-glutamic acid semialdehyde n-Acetyl-L-glutamic acid-5-semialdehyde N-Acetyl-L-glutamic acid-5-semialdehyde n-Acetylglutamate γ-semialdehyde N-Acetylglutamate g-semialdehyde N-Acetylglutamate gamma-semialdehyde N-Acetylglutamate semialdehyde N-Acetylglutamate γ-semialdehyde n-Acetylglutamic acid γ-semialdehyde N-Acetylglutamic acid g-semialdehyde N-Acetylglutamic acid gamma-semialdehyde N-Acetylglutamic acid semialdehyde N-Acetylglutamic acid γ-semialdehyde N-AcGlu-semialdehyde C7H11NO4 173.1665 173.068807845 (2S)-2-acetamido-5-oxopentanoic acid N-acetyl-5-oxo-L-norvaline 13074-21-0 CC(=O)N[C@@H](CCC=O)C(O)=O InChI=1S/C7H11NO4/c1-5(10)8-6(7(11)12)3-2-4-9/h4,6H,2-3H2,1H3,(H,8,10)(H,11,12)/t6-/m0/s1 BCPSFKBPHHBDAI-LURJTMIESA-N Solid Cytosol logp -0.43 ALOGPS logs -0.97 ALOGPS solubility 1.86e+01 g/l ALOGPS logp -1.3 ChemAxon pka_strongest_acidic 3.72 ChemAxon pka_strongest_basic -1.8 ChemAxon iupac (2S)-2-acetamido-5-oxopentanoic acid ChemAxon average_mass 173.1665 ChemAxon mono_mass 173.068807845 ChemAxon smiles CC(=O)N[C@@H](CCC=O)C(O)=O ChemAxon formula C7H11NO4 ChemAxon inchi InChI=1S/C7H11NO4/c1-5(10)8-6(7(11)12)3-2-4-9/h4,6H,2-3H2,1H3,(H,8,10)(H,11,12)/t6-/m0/s1 ChemAxon inchikey BCPSFKBPHHBDAI-LURJTMIESA-N ChemAxon polar_surface_area 83.47 ChemAxon refractivity 39.81 ChemAxon polarizability 16.46 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 4 ChemAxon donor_count 2 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Arginine and proline metabolism ec00330 Lysine biosynthesis Lysine is biosynthesized from L-aspartic acid. L-aspartic acid can be incorporated into the cell through various methods: C4 dicarboxylate / orotate:H+ symporter , glutamate / aspartate : H+ symporter GltP, dicarboxylate transporter , C4 dicarboxylate / C4 monocarboxylate transporter DauA, glutamate / aspartate ABC transporter L-aspartic acid is phosphorylated by an ATP-driven Aspartate kinase resulting in ADP and L-aspartyl-4-phosphate. L-aspartyl-4-phosphate is then dehydrogenated through an NADPH driven aspartate semialdehyde dehydrogenase resulting in a release of phosphate, NADP and L-aspartic 4-semialdehyde (involved in methionine biosynthesis). L-aspartic 4-semialdehyde interacts with a pyruvic acid through a 4-hydroxy-tetrahydrodipicolinate synthase resulting in a release of hydrogen ion, water and (2S,4S)-4-hydroxy-2,3,4,5-tetrahydrodipicolinate. The latter compound is then reduced by an NADPH driven 4-hydroxy-tetrahydrodipicolinate reductase resulting in a release of water, NADP and (S)-2,3,4,5-tetrahydrodipicolinate, This compound interacts with succinyl-CoA and water through a tetrahydrodipicolinate succinylase resulting in a release of coenzyme A and N-Succinyl-2-amino-6-ketopimelate. This compound interacts with L-glutamic acid through a N-succinyldiaminopimelate aminotransferase resulting in oxoglutaric acid, N-succinyl-L,L-2,6-diaminopimelate. The latter compound is then desuccinylated by reacting with water through a N-succinyl-L-diaminopimelate desuccinylase resulting in a succinic acid and L,L-diaminopimelate. This compound is then isomerized through a diaminopimelate epimerase resulting in a meso-diaminopimelate (involved in peptidoglyccan biosynthesis I). This compound is then decarboxylated by a diaminopimelate decarboxylase resulting in a release of carbon dioxide and L-lysine. L-lysine is then incorporated into lysine degradation pathway. Lysine also regulate its own biosynthesis by repressing dihydrodipicolinate synthase and also repressing lysine-sensitive aspartokinase 3. A metabolic connection joins synthesis of an amino acid, lysine, to synthesis of cell wall material. Diaminopimelate is a precursor both for lysine and for cell wall components. The synthesis of lysine, methionine and threonine share two reactions at the start of the three pathways, the reactions converting L-aspartate to L-aspartate semialdehyde. The reaction involving aspartate kinase is carried out by three isozymes, one specific for synthesis of each end product amino acid. Each of the three aspartate kinase isozymes is regulated by its corresponding end product amino acid. PW000771 ec00300 Metabolic 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 3024 Specdb::CMs 39028 Specdb::CMs 160845 Specdb::NmrOneD 74572 Specdb::NmrOneD 74573 Specdb::NmrOneD 74574 Specdb::NmrOneD 74575 Specdb::NmrOneD 74576 Specdb::NmrOneD 74577 Specdb::NmrOneD 74578 Specdb::NmrOneD 74579 Specdb::NmrOneD 74580 Specdb::NmrOneD 74581 Specdb::NmrOneD 74582 Specdb::NmrOneD 74583 Specdb::NmrOneD 74584 Specdb::NmrOneD 74585 Specdb::NmrOneD 74586 Specdb::NmrOneD 74587 Specdb::NmrOneD 74588 Specdb::NmrOneD 74589 Specdb::NmrOneD 74590 Specdb::NmrOneD 74591 Specdb::MsMs 24596 Specdb::MsMs 24597 Specdb::MsMs 24598 Specdb::MsMs 31154 Specdb::MsMs 31155 Specdb::MsMs 31156 Specdb::MsMs 2416708 Specdb::MsMs 2416709 Specdb::MsMs 2416710 Specdb::MsMs 2548987 Specdb::MsMs 2548988 Specdb::MsMs 2548989 HMDB06488 192878 167387 C01250 16319 CPD-469 Keseler, I. 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Villanova University: U.S.A N-acetyl-gamma-glutamyl-phosphate reductase P11446 ARGC_ECOLI argC http://ecmdb.ca/proteins/P11446.xml Acetylornithine/succinyldiaminopimelate aminotransferase P18335 ARGD_ECOLI argD http://ecmdb.ca/proteins/P18335.xml Acetylornithine deacetylase P23908 ARGE_ECOLI argE http://ecmdb.ca/proteins/P23908.xml Succinylornithine transaminase P77581 ASTC_ECOLI astC http://ecmdb.ca/proteins/P77581.xml N-Acetylornithine + alpha-Ketoglutarate <> N-Acetyl-L-glutamate 5-semialdehyde + L-Glutamate R02283 N-Acetyl-L-glutamate 5-semialdehyde + Water > Acetic acid + L-Glutamic-gamma-semialdehyde N-Acetyl-L-glutamate 5-semialdehyde + NADP + Phosphate <> N-Acetyl-L-glutamyl 5-phosphate + Hydrogen ion + NADPH R03443 N-ACETYLGLUTPREDUCT-RXN N-Acetylornithine + Oxoglutaric acid < N-Acetyl-L-glutamate 5-semialdehyde + L-Glutamate ACETYLORNTRANSAM-RXN N-Acetyl-L-glutamate 5-semialdehyde + NADP + Inorganic phosphate > N-Acetyl-L-glutamyl 5-phosphate + NADPH N-Acetylornithine + Oxoglutaric acid > N-Acetyl-L-glutamate 5-semialdehyde + L-Glutamate N-Acetyl-L-glutamate 5-semialdehyde + L-Glutamic acid + L-Glutamate > Oxoglutaric acid + N-Acetylornithine PW_R002675 N-Acetyl-L-glutamate 5-semialdehyde + NADP + Phosphate <> N-Acetyl-L-glutamyl 5-phosphate + Hydrogen ion + NADPH N-Acetylornithine + alpha-Ketoglutarate <> N-Acetyl-L-glutamate 5-semialdehyde + L-Glutamate