2.0 2015-09-08 17:49:59 -0600 2015-09-14 16:46:11 -0600 ECMDB24190 M2MDB006307 N2-succinyl-L-arginine N2-Succinyl-L-arginine belongs to the class of Amino Fatty Acids. These are fatty acids contaning an amine group. (inferred from compound structure) C10H17N4O5 273.27 273.120443243 (2S)-5-{[amino(iminiumyl)methyl]amino}-2-(3-carboxylatopropanamido)pentanoate N(2)-succinyl-L-arginine NC(=[NH2+])NCCC[C@H](NC(=O)CCC([O-])=O)C([O-])=O InChI=1S/C10H18N4O5/c11-10(12)13-5-1-2-6(9(18)19)14-7(15)3-4-8(16)17/h6H,1-5H2,(H,14,15)(H,16,17)(H,18,19)(H4,11,12,13)/p-1/t6-/m0/s1 UMOXFSXIFQOWTD-LURJTMIESA-M logp -0.20 ALOGPS logs -1.29 ALOGPS solubility 1.75e+01 g/l ALOGPS logp -3.8 ChemAxon pka_strongest_acidic 3.28 ChemAxon pka_strongest_basic 12.15 ChemAxon iupac (2S)-5-{[amino(iminiumyl)methyl]amino}-2-(3-carboxylatopropanamido)pentanoate ChemAxon average_mass 273.27 ChemAxon mono_mass 273.120443243 ChemAxon smiles NC(=[NH2+])NCCC[C@H](NC(=O)CCC([O-])=O)C([O-])=O ChemAxon formula C10H17N4O5 ChemAxon inchi InChI=1S/C10H18N4O5/c11-10(12)13-5-1-2-6(9(18)19)14-7(15)3-4-8(16)17/h6H,1-5H2,(H,14,15)(H,16,17)(H,18,19)(H4,11,12,13)/p-1/t6-/m0/s1 ChemAxon inchikey UMOXFSXIFQOWTD-LURJTMIESA-M ChemAxon polar_surface_area 173 ChemAxon refractivity 96.73 ChemAxon polarizability 26.4 ChemAxon rotatable_bond_count 9 ChemAxon acceptor_count 7 ChemAxon donor_count 4 ChemAxon physiological_charge -1 ChemAxon formal_charge -1 ChemAxon 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 Specdb::MsMs 28649 Specdb::MsMs 28650 Specdb::MsMs 28651 Specdb::MsMs 35207 Specdb::MsMs 35208 Specdb::MsMs 35209 Arginine N-succinyltransferase P0AE37 ASTA_ECOLI astA http://ecmdb.ca/proteins/P0AE37.xml N-succinylarginine dihydrolase P76216 ASTB_ECOLI astB http://ecmdb.ca/proteins/P76216.xml L-Arginine + Succinyl-CoA + Succinyl-CoA > Coenzyme A + Hydrogen ion + N2-succinyl-L-arginine + N2-succinyl-L-arginine PW_R002678 N2-succinyl-L-arginine + 2 Water + 2 Hydrogen ion + N2-succinyl-L-arginine > Carbon dioxide +2 Ammonium + N2-Succinyl-L-ornithine PW_R002679