2.0 2012-05-31 13:03:22 -0600 2015-09-13 12:56:09 -0600 ECMDB01006 M2MDB000224 Argininosuccinic acid Arginosuccinic acid is a basic amino acid. Some cells synthesize it from citrulline, aspartic acid and use it as a precursor for arginine in the urea cycle or citrulline-NO cycle. The enzyme that catalyzes the reaction is argininosuccinate synthetase. Argininosuccinic acid is a precursor to fumarate in the citric acid cycle via argininosuccinate lyase. 2-(N(Omega)-L-arginine)succinate 2-(N(Omega)-L-arginine)succinic acid 2-(N(Omega)-L-arginino)succinate 2-(N(Omega)-L-arginino)succinic acid 2-(Nw-L-arginino)butanedioate 2-(Nw-L-arginino)butanedioic acid Argininosuccinate Argininosuccinic acid Arginosuccinate Arginosuccinic acid ArgSuccinate ArgSuccinic acid ASA L-Argininosuccinate L-Argininosuccinic acid L-Arginosuccinate L-Arginosuccinic acid N(Omega)-(L-arginino)succinate N(Omega)-(L-arginino)succinic acid N-(((4-Amino-4-carboxybutyl)amino)iminomethyl)-L-Aspartate N-(((4-Amino-4-carboxybutyl)amino)iminomethyl)-L-Aspartic acid N-(L-Arginino) succinate N-(L-Arginino) succinic acid N-(L-Arginino)succinate N-(L-Arginino)succinic acid N-[(4-Amino-4-carboxybutyl)amidino]-L-Aspartate N-[(4-Amino-4-carboxybutyl)amidino]-L-Aspartic acid N-[[(4-Amino-4-carboxybutyl)amino]iminomethyl]-L-Aspartate N-[[(4-Amino-4-carboxybutyl)amino]iminomethyl]-L-Aspartic acid C10H18N4O6 290.2731 290.122634328 (2S)-2-{N'-[(4S)-4-amino-4-carboxybutyl]carbamimidamido}butanedioic acid argininosuccinic acid 2387-71-5 N[C@@H](CCCNC(=N)N[C@@H](CC(O)=O)C(O)=O)C(O)=O InChI=1S/C10H18N4O6/c11-5(8(17)18)2-1-3-13-10(12)14-6(9(19)20)4-7(15)16/h5-6H,1-4,11H2,(H,15,16)(H,17,18)(H,19,20)(H3,12,13,14)/t5-,6-/m0/s1 KDZOASGQNOPSCU-WDSKDSINSA-N Solid Cytosol logp -3.25 ALOGPS logs -2.80 ALOGPS solubility 4.56e-01 g/l ALOGPS logp -5.8 ChemAxon pka_strongest_acidic 2.14 ChemAxon pka_strongest_basic 12.39 ChemAxon iupac (2S)-2-{N'-[(4S)-4-amino-4-carboxybutyl]carbamimidamido}butanedioic acid ChemAxon average_mass 290.2731 ChemAxon mono_mass 290.122634328 ChemAxon smiles N[C@@H](CCCNC(=N)N[C@@H](CC(O)=O)C(O)=O)C(O)=O ChemAxon formula C10H18N4O6 ChemAxon inchi InChI=1S/C10H18N4O6/c11-5(8(17)18)2-1-3-13-10(12)14-6(9(19)20)4-7(15)16/h5-6H,1-4,11H2,(H,15,16)(H,17,18)(H,19,20)(H3,12,13,14)/t5-,6-/m0/s1 ChemAxon inchikey KDZOASGQNOPSCU-WDSKDSINSA-N ChemAxon polar_surface_area 185.83 ChemAxon refractivity 75.31 ChemAxon polarizability 27.6 ChemAxon rotatable_bond_count 9 ChemAxon acceptor_count 10 ChemAxon donor_count 7 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Alanine, aspartate and glutamate metabolism ec00250 Arginine and proline metabolism ec00330 Metabolic pathways eco01100 Aspartate metabolism Aspartate (seen in the center) is synthesized from and degraded to oxaloacetate , an intermediate of the TCA cycle, by a reversible transamination reaction with glutamate. As shown here, AspC is the principal transaminase that catalyzes this reaction, but TyrB also catalyzes it. Null mutations in aspC do not confer aspartate auxotrophy; null mutations in both aspC and tyrB do. Aspartate is a constituent of proteins and participates in several other biosyntheses as shown here( NAD biosynthesis and Beta-Alanine Metabolism . Approximately 27 percent of the cell's nitrogen flows through aspartate Aspartate can be synthesized from fumaric acid through a aspartate ammonia lyase. Aspartate also participates in the synthesis of L-asparagine through two different methods, either through aspartate ammonia ligase or asparagine synthetase B. Aspartate is also a precursor of fumaric acid. Again it has two possible ways of synthesizing it. First set of reactions follows an adenylo succinate synthetase that yields adenylsuccinic acid and then adenylosuccinate lyase in turns leads to fumaric acid. The second way is through argininosuccinate synthase that yields argininosuccinic acid and then argininosuccinate lyase in turns leads to fumaric acid PW000787 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 Specdb::CMs 858 Specdb::CMs 11925 Specdb::CMs 37267 Specdb::CMs 134041 Specdb::CMs 141775 Specdb::CMs 1048353 Specdb::CMs 1048355 Specdb::CMs 1048356 Specdb::CMs 1048358 Specdb::CMs 1048360 Specdb::CMs 1048362 Specdb::CMs 1048364 Specdb::CMs 1048366 Specdb::CMs 1048368 Specdb::CMs 1048370 Specdb::CMs 1048372 Specdb::CMs 1048373 Specdb::CMs 1048376 Specdb::CMs 1048378 Specdb::CMs 1048379 Specdb::CMs 1048381 Specdb::CMs 1048383 Specdb::CMs 1048385 Specdb::CMs 1048387 Specdb::CMs 1048389 Specdb::NmrOneD 1054 Specdb::NmrOneD 250728 Specdb::NmrOneD 250729 Specdb::NmrOneD 250730 Specdb::NmrOneD 250731 Specdb::NmrOneD 250732 Specdb::NmrOneD 250733 Specdb::NmrOneD 250734 Specdb::NmrOneD 250735 Specdb::NmrOneD 250736 Specdb::NmrOneD 250737 Specdb::NmrOneD 250738 Specdb::NmrOneD 250739 Specdb::NmrOneD 250740 Specdb::NmrOneD 250741 Specdb::NmrOneD 250742 Specdb::NmrOneD 250743 Specdb::NmrOneD 250744 Specdb::NmrOneD 250745 Specdb::NmrOneD 250746 Specdb::NmrOneD 250747 Specdb::MsMs 6191 Specdb::MsMs 6192 Specdb::MsMs 6193 Specdb::MsMs 6194 Specdb::MsMs 6195 Specdb::MsMs 6196 Specdb::MsMs 6197 Specdb::MsMs 6198 Specdb::MsMs 6199 Specdb::MsMs 6200 Specdb::MsMs 6201 Specdb::MsMs 6202 Specdb::MsMs 6203 Specdb::MsMs 6204 Specdb::MsMs 6205 Specdb::MsMs 6206 Specdb::MsMs 6207 Specdb::MsMs 6208 Specdb::MsMs 292258 Specdb::MsMs 292259 Specdb::MsMs 292260 Specdb::MsMs 332410 Specdb::MsMs 332411 Specdb::MsMs 332412 Specdb::MsMs 437142 Specdb::NmrTwoD 1112 HMDB00052 439998 17215918 C03406 15682 Argininosuccinic acid 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 Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. 18331064 Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. 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Kokai Tokkyo Koho (1980), 3 pp. http://hmdb.ca/system/metabolites/msds/000/000/037/original/HMDB00052.pdf?1358462827 Argininosuccinate synthase P0A6E4 ASSY_ECOLI argG http://ecmdb.ca/proteins/P0A6E4.xml Argininosuccinate lyase P11447 ARLY_ECOLI argH http://ecmdb.ca/proteins/P11447.xml L-Aspartic acid + Adenosine triphosphate + Citrulline <> Adenosine monophosphate + Argininosuccinic acid + Hydrogen ion + Pyrophosphate R01954 Argininosuccinic acid <> L-Arginine + Fumaric acid R01086 Adenosine triphosphate + Citrulline + L-Aspartic acid <> Adenosine monophosphate + Pyrophosphate + Argininosuccinic acid R01954 Adenosine triphosphate + Citrulline + L-Aspartic acid + L-Aspartic acid > Pyrophosphate + Adenosine monophosphate + Argininosuccinic acid PW_R002649 Argininosuccinic acid > Fumaric acid + L-Arginine PW_R002652 L-Aspartic acid + Adenosine triphosphate + Citrulline <> Adenosine monophosphate + Argininosuccinic acid + Hydrogen ion + Pyrophosphate Argininosuccinic acid <> L-Arginine + Fumaric acid L-Aspartic acid + Adenosine triphosphate + Citrulline <> Adenosine monophosphate + Argininosuccinic acid + Hydrogen ion + Pyrophosphate