2.0 2012-05-31 13:47:30 -0600 2015-06-03 15:53:50 -0600 ECMDB01199 M2MDB000295 N2-Succinyl-L-ornithine N2-Succinyl-L-ornithine is a substrate for Ornithine aminotransferase (mitochondrial). N2-Succinyl-L-ornithine N2-succinylornithine N2SucOrn N<SUP>2</SUP>-succinylornithine C9H16N2O5 232.2337 232.105921632 (2S)-5-amino-2-(3-carboxypropanamido)pentanoic acid N(2)-succinyl-L-ornithine 899816-95-6 NCCC[C@H](NC(=O)CCC(O)=O)C(O)=O InChI=1S/C9H16N2O5/c10-5-1-2-6(9(15)16)11-7(12)3-4-8(13)14/h6H,1-5,10H2,(H,11,12)(H,13,14)(H,15,16)/t6-/m0/s1 VWXQFHJBQHTHMK-LURJTMIESA-N Solid Cytosol logp -3.37 ALOGPS logs -1.08 ALOGPS solubility 1.93e+01 g/l ALOGPS logp -4.1 ChemAxon pka_strongest_acidic 3.32 ChemAxon pka_strongest_basic 9.9 ChemAxon iupac (2S)-5-amino-2-(3-carboxypropanamido)pentanoic acid ChemAxon average_mass 232.2337 ChemAxon mono_mass 232.105921632 ChemAxon smiles NCCC[C@H](NC(=O)CCC(O)=O)C(O)=O ChemAxon formula C9H16N2O5 ChemAxon inchi InChI=1S/C9H16N2O5/c10-5-1-2-6(9(15)16)11-7(12)3-4-8(13)14/h6H,1-5,10H2,(H,11,12)(H,13,14)(H,15,16)/t6-/m0/s1 ChemAxon inchikey VWXQFHJBQHTHMK-LURJTMIESA-N ChemAxon polar_surface_area 129.72 ChemAxon refractivity 53.55 ChemAxon polarizability 22.77 ChemAxon rotatable_bond_count 8 ChemAxon acceptor_count 6 ChemAxon donor_count 4 ChemAxon physiological_charge -1 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 18900 Specdb::CMs 37970 Specdb::CMs 170852 Specdb::NmrOneD 21442 Specdb::NmrOneD 21443 Specdb::NmrOneD 21444 Specdb::NmrOneD 21445 Specdb::NmrOneD 21446 Specdb::NmrOneD 21447 Specdb::NmrOneD 21448 Specdb::NmrOneD 21449 Specdb::NmrOneD 21450 Specdb::NmrOneD 21451 Specdb::NmrOneD 21452 Specdb::NmrOneD 21453 Specdb::NmrOneD 21454 Specdb::NmrOneD 21455 Specdb::NmrOneD 21456 Specdb::NmrOneD 21457 Specdb::NmrOneD 21458 Specdb::NmrOneD 21459 Specdb::NmrOneD 21460 Specdb::NmrOneD 21461 Specdb::MsMs 24881 Specdb::MsMs 24882 Specdb::MsMs 24883 Specdb::MsMs 31439 Specdb::MsMs 31440 Specdb::MsMs 31441 Specdb::MsMs 2710214 Specdb::MsMs 2710215 Specdb::MsMs 2710216 Specdb::MsMs 2994728 Specdb::MsMs 2994729 Specdb::MsMs 2994730 HMDB01199 920 113025 C03415 N2-SUCCINYLORNITHINE SUO 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-succinylarginine dihydrolase P76216 ASTB_ECOLI astB http://ecmdb.ca/proteins/P76216.xml Succinylornithine transaminase P77581 ASTC_ECOLI astC http://ecmdb.ca/proteins/P77581.xml 2 Hydrogen ion + 2 Water + N2-Succinyl-L-arginine > Carbon dioxide +2 Ammonium + N2-Succinyl-L-ornithine alpha-Ketoglutarate + N2-Succinyl-L-ornithine <> L-Glutamate + N2-Succinyl-L-glutamic acid 5-semialdehyde R04217 N2-Succinyl-L-arginine + 2 Water <> N2-Succinyl-L-ornithine + Carbon dioxide +2 Ammonia R04189 N2-Succinyl-L-arginine + Water > N2-Succinyl-L-ornithine + Ammonia + Carbon dioxide R04189 SUCCARGDIHYDRO-RXN N2-Succinyl-L-ornithine + Oxoglutaric acid > N2-Succinyl-L-glutamic acid 5-semialdehyde + L-Glutamate SUCCORNTRANSAM-RXN N2-Succinyl-L-arginine + 2 Water > N2-Succinyl-L-ornithine +2 Ammonia + Carbon dioxide N2-succinyl-L-arginine + 2 Water + 2 Hydrogen ion + N2-succinyl-L-arginine > Carbon dioxide +2 Ammonium + N2-Succinyl-L-ornithine PW_R002679 N2-Succinyl-L-ornithine + Oxoglutaric acid > L-Glutamic acid + N2-Succinyl-L-glutamic acid 5-semialdehyde + L-Glutamate PW_R002680 N2-Succinyl-L-arginine + 2 Water <> N2-Succinyl-L-ornithine + Carbon dioxide +2 Ammonia N2-Succinyl-L-arginine + 2 Water <> N2-Succinyl-L-ornithine + Carbon dioxide +2 Ammonia