2.0 2012-05-31 13:47:03 -0600 2015-06-03 15:53:49 -0600 ECMDB01180 M2MDB000287 N2-Succinyl-L-glutamic acid 5-semialdehyde N2-Succinyl-L-glutamic acid 5-semialdehyde is a substrate for Succinate semialdehyde dehydrogenase (mitochondrial) and Ornithine aminotransferase (mitochondrial). N2-Succinyl-L-glutamate 5-semialdehyde N2-succinylglutamate semialdehyde N2-succinylglutamic acid semialdehyde N2-succinylglutamic semialdehyde N2-succinylglutamic-semialdehyde N2SucGluSA N²-succinylglutamate semialdehyde N²-succinylglutamic semialdehyde N²-succinylglutamic-semialdehyde C9H13NO6 231.2026 231.074287153 (2S)-2-(3-carboxypropanamido)-5-oxopentanoic acid (2S)-2-(3-carboxypropanamido)-5-oxopentanoic acid OC(=O)CCC(=O)N[C@@H](CCC=O)C(O)=O InChI=1S/C9H13NO6/c11-5-1-2-6(9(15)16)10-7(12)3-4-8(13)14/h5-6H,1-4H2,(H,10,12)(H,13,14)(H,15,16)/t6-/m0/s1 XTOKIEIBKARFSZ-LURJTMIESA-N Solid Cytosol logp -0.81 ALOGPS logs -1.62 ALOGPS solubility 5.57e+00 g/l ALOGPS logp -1.4 ChemAxon pka_strongest_acidic 3.38 ChemAxon pka_strongest_basic -1.5 ChemAxon iupac (2S)-2-(3-carboxypropanamido)-5-oxopentanoic acid ChemAxon average_mass 231.2026 ChemAxon mono_mass 231.074287153 ChemAxon smiles OC(=O)CCC(=O)N[C@@H](CCC=O)C(O)=O ChemAxon formula C9H13NO6 ChemAxon inchi InChI=1S/C9H13NO6/c11-5-1-2-6(9(15)16)10-7(12)3-4-8(13)14/h5-6H,1-4H2,(H,10,12)(H,13,14)(H,15,16)/t6-/m0/s1 ChemAxon inchikey XTOKIEIBKARFSZ-LURJTMIESA-N ChemAxon polar_surface_area 120.77 ChemAxon refractivity 50.7 ChemAxon polarizability 21.38 ChemAxon rotatable_bond_count 8 ChemAxon acceptor_count 6 ChemAxon donor_count 3 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon Arginine and proline metabolism ec00330 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 arginine degradation II (AST pathway) AST-PWY Specdb::CMs 24304 Specdb::CMs 37961 Specdb::CMs 147690 Specdb::NmrOneD 146670 Specdb::NmrOneD 146671 Specdb::NmrOneD 146672 Specdb::NmrOneD 146673 Specdb::NmrOneD 146674 Specdb::NmrOneD 146675 Specdb::NmrOneD 146676 Specdb::NmrOneD 146677 Specdb::NmrOneD 146678 Specdb::NmrOneD 146679 Specdb::NmrOneD 146680 Specdb::NmrOneD 146681 Specdb::NmrOneD 146682 Specdb::NmrOneD 146683 Specdb::NmrOneD 146684 Specdb::NmrOneD 146685 Specdb::NmrOneD 146686 Specdb::NmrOneD 146687 Specdb::NmrOneD 146688 Specdb::NmrOneD 146689 Specdb::MsMs 27332 Specdb::MsMs 27333 Specdb::MsMs 27334 Specdb::MsMs 33890 Specdb::MsMs 33891 Specdb::MsMs 33892 Specdb::MsMs 2777396 Specdb::MsMs 2777397 Specdb::MsMs 2777398 Specdb::MsMs 2900673 Specdb::MsMs 2900674 Specdb::MsMs 2900675 HMDB01180 556 389690 C05932 CPD-822 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 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 N-succinylglutamate 5-semialdehyde dehydrogenase P76217 ASTD_ECOLI astD http://ecmdb.ca/proteins/P76217.xml Succinylornithine transaminase P77581 ASTC_ECOLI astC http://ecmdb.ca/proteins/P77581.xml Water + NAD + N2-Succinyl-L-glutamic acid 5-semialdehyde <>2 Hydrogen ion + NADH + N-Succinyl-L-glutamate R05049 alpha-Ketoglutarate + N2-Succinyl-L-ornithine <> L-Glutamate + N2-Succinyl-L-glutamic acid 5-semialdehyde R04217 N2-Succinyl-L-glutamic acid 5-semialdehyde + NAD + Water <> N-Succinyl-L-glutamate + NADH + Hydrogen ion R05049 N2-Succinyl-L-glutamic acid 5-semialdehyde + NAD + Water > N<SUP>2</SUP>-succinylglutamate + NADH + Hydrogen ion SUCCGLUALDDEHYD-RXN N2-Succinyl-L-ornithine + Oxoglutaric acid > N2-Succinyl-L-glutamic acid 5-semialdehyde + L-Glutamate SUCCORNTRANSAM-RXN N2-Succinyl-L-glutamic acid 5-semialdehyde + NAD + Water > N-Succinyl-L-glutamate + NADH N2-Succinyl-L-ornithine + Oxoglutaric acid > L-Glutamic acid + N2-Succinyl-L-glutamic acid 5-semialdehyde + L-Glutamate PW_R002680 N2-Succinyl-L-glutamic acid 5-semialdehyde + Water + NAD >2 Hydrogen ion + NADH + N2-succinylglutamate + N2-succinylglutamate PW_R002681 Water + NAD + N2-Succinyl-L-glutamic acid 5-semialdehyde <>2 Hydrogen ion + NADH + N-Succinyl-L-glutamate