2.0 2012-05-31 13:01:23 -0600 2015-09-13 12:56:09 -0600 ECMDB00828 M2MDB000189 Ureidosuccinic acid Ureidosuccinic acid is an intermediary product in pyrimidine metabolism. It is generated by the action of dihydroorotase which catalyzes the following reaction: 4,5-Dihydroorotic acid + Water <=> Ureidosuccinic acid + H+ 2-Ureidobutanedioate 2-Ureidobutanedioic acid Carbamoyl-Asp Carbamoyl-aspartate Carbamoyl-aspartic acid Carbamoylaspartate Carbamoylaspartic acid Carbamyl-aspartate Carbamyl-aspartic acid Carbamyl-L-aspartate Carbamyl-L-aspartic acid Carbamylaspartate Carbamylaspartic acid Carbamyul-aspartate Carbamyul-aspartic acid Carbamyul-L-aspartate Carbamyul-L-aspartic acid L-N-Carbamoylaspartate L-N-Carbamoylaspartic acid L-Ureidosuccinate L-Ureidosuccinic acid N-(Aminocarbonyl)-L-aspartate N-(Aminocarbonyl)-L-aspartic acid N-Carbamoyl-L-aspartate N-Carbamoyl-L-aspartic acid N-Carbamoyl-S-aspartate N-Carbamoyl-S-aspartic acid N-Carbamoylaspartate N-Carbamoylaspartic acid NCD Ureidosuccinate C5H8N2O5 176.1274 176.043321376 (2S)-2-(carbamoylamino)butanedioic acid carbamylaspartic acid 13184-27-5 NC(=O)N[C@@H](CC(O)=O)C(O)=O InChI=1S/C5H8N2O5/c6-5(12)7-2(4(10)11)1-3(8)9/h2H,1H2,(H,8,9)(H,10,11)(H3,6,7,12)/t2-/m0/s1 HLKXYZVTANABHZ-REOHCLBHSA-N Solid Cytosol logp -1.12 ALOGPS logs -0.92 ALOGPS solubility 2.13e+01 g/l ALOGPS melting_point 174 - 175 oC logp -1.7 ChemAxon pka_strongest_acidic 3.33 ChemAxon pka_strongest_basic -2.6 ChemAxon iupac (2S)-2-(carbamoylamino)butanedioic acid ChemAxon average_mass 176.1274 ChemAxon mono_mass 176.043321376 ChemAxon smiles NC(=O)N[C@@H](CC(O)=O)C(O)=O ChemAxon formula C5H8N2O5 ChemAxon inchi InChI=1S/C5H8N2O5/c6-5(12)7-2(4(10)11)1-3(8)9/h2H,1H2,(H,8,9)(H,10,11)(H3,6,7,12)/t2-/m0/s1 ChemAxon inchikey HLKXYZVTANABHZ-REOHCLBHSA-N ChemAxon polar_surface_area 129.72 ChemAxon refractivity 34.65 ChemAxon polarizability 14.72 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 5 ChemAxon donor_count 4 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon Alanine, aspartate and glutamate metabolism ec00250 Pyrimidine metabolism The metabolism of pyrimidines begins with L-glutamine interacting with water molecule and a hydrogen carbonate through an ATP driven carbamoyl phosphate synthetase resulting in a hydrogen ion, an ADP, a phosphate, an L-glutamic acid and a carbamoyl phosphate. The latter compound interacts with an L-aspartic acid through a aspartate transcarbamylase resulting in a phosphate, a hydrogen ion and a N-carbamoyl-L-aspartate. The latter compound interacts with a hydrogen ion through a dihydroorotase resulting in the release of a water molecule and a 4,5-dihydroorotic acid. This compound interacts with an ubiquinone-1 through a dihydroorotate dehydrogenase, type 2 resulting in a release of an ubiquinol-1 and an orotic acid. The orotic acid then interacts with a phosphoribosyl pyrophosphate through a orotate phosphoribosyltransferase resulting in a pyrophosphate and an orotidylic acid. The latter compound then interacts with a hydrogen ion through an orotidine-5 '-phosphate decarboxylase, resulting in an release of carbon dioxide and an Uridine 5' monophosphate. The Uridine 5' monophosphate process to get phosphorylated by an ATP driven UMP kinase resulting in the release of an ADP and an Uridine 5--diphosphate. Uridine 5-diphosphate can be metabolized in multiple ways in order to produce a Deoxyuridine triphosphate. 1.-Uridine 5-diphosphate interacts with a reduced thioredoxin through a ribonucleoside diphosphate reductase 1 resulting in the release of a water molecule and an oxidized thioredoxin and an dUDP. The dUDP is then phosphorylated by an ATP through a nucleoside diphosphate kinase resulting in the release of an ADP and a DeoxyUridine triphosphate. 2.-Uridine 5-diphosphate interacts with a reduced NrdH glutaredoxin-like protein through a Ribonucleoside-diphosphate reductase 1 resulting in a release of a water molecule, an oxidized NrdH glutaredoxin-like protein and a dUDP. The dUDP is then phosphorylated by an ATP through a nucleoside diphosphate kinase resulting in the release of an ADP and a DeoxyUridine triphosphate. 3.-Uridine 5-diphosphate is phosphorylated by an ATP-driven nucleoside diphosphate kinase resulting in an ADP and an Uridinetriphosphate. The latter compound interacts with a reduced flavodoxin through ribonucleoside-triphosphate reductase resulting in the release of an oxidized flavodoxin, a water molecule and a Deoxyuridine triphosphate 4.-Uridine 5-diphosphate is phosphorylated by an ATP-driven nucleoside diphosphate kinase resulting in an ADP and an Uridinetriphosphate The uridine triphosphate interacts with a L-glutamine and a water molecule through an ATP driven CTP synthase resulting in an ADP, a phosphate, a hydrogen ion, an L-glutamic acid and a cytidine triphosphate. The cytidine triphosphate interacts with a reduced flavodoxin through a ribonucleoside-triphosphate reductase resulting in the release of a water molecule, an oxidized flavodoxin and a dCTP. The dCTP interacts with a water molecule and a hydrogen ion through a dCTP deaminase resulting in a release of an ammonium molecule and a Deoxyuridine triphosphate. 5.-Uridine 5-diphosphate is phosphorylated by an ATP-driven nucleoside diphosphate kinase resulting in an ADP and an Uridinetriphosphate The uridine triphosphate interacts with a L-glutamine and a water molecule through an ATP driven CTP synthase resulting in an ADP, a phosphate, a hydrogen ion, an L-glutamic acid and a cytidine triphosphate. The cytidine triphosphate then interacts spontaneously with a water molecule resulting in the release of a phosphate, a hydrogen ion and a CDP. The CDP then interacts with a reduced NrdH glutaredoxin-like protein through a ribonucleoside-diphosphate reductase 2 resulting in the release of a water molecule, an oxidized NrdH glutaredoxin-like protein and a dCDP. The dCDP is then phosphorylated through an ATP driven nucleoside diphosphate kinase resulting in an ADP and a dCTP. The dCTP interacts with a water molecule and a hydrogen ion through a dCTP deaminase resulting in a release of an ammonium molecule and a Deoxyuridine triphosphate. 6.-Uridine 5-diphosphate is phosphorylated by an ATP-driven nucleoside diphosphate kinase resulting in an ADP and an Uridinetriphosphate The uridine triphosphate interacts with a L-glutamine and a water molecule through an ATP driven CTP synthase resulting in an ADP, a phosphate, a hydrogen ion, an L-glutamic acid and a cytidine triphosphate. The cytidine triphosphate then interacts spontaneously with a water molecule resulting in the release of a phosphate, a hydrogen ion and a CDP. The CDP interacts with a reduced thioredoxin through a ribonucleoside diphosphate reductase 1 resulting in a release of a water molecule, an oxidized thioredoxin and a dCDP. The dCDP is then phosphorylated through an ATP driven nucleoside diphosphate kinase resulting in an ADP and a dCTP. The dCTP interacts with a water molecule and a hydrogen ion through a dCTP deaminase resulting in a release of an ammonium molecule and a Deoxyuridine triphosphate. The deoxyuridine triphosphate then interacts with a water molecule through a nucleoside triphosphate pyrophosphohydrolase resulting in a release of a hydrogen ion, a phosphate and a dUMP. The dUMP then interacts with a methenyltetrahydrofolate through a thymidylate synthase resulting in a dihydrofolic acid and a 5-thymidylic acid. Then 5-thymidylic acid is then phosphorylated through a nucleoside diphosphate kinase resulting in the release of an ADP and thymidine 5'-triphosphate. PW000942 ec00240 Metabolic Metabolic pathways eco01100 uridine-5'-phosphate biosynthesis PWY-5686 Specdb::CMs 1509 Specdb::CMs 1664 Specdb::CMs 3426 Specdb::CMs 30107 Specdb::CMs 31239 Specdb::CMs 31240 Specdb::CMs 37790 Specdb::CMs 154368 Specdb::CMs 1077681 Specdb::CMs 1077683 Specdb::CMs 1077684 Specdb::CMs 1077686 Specdb::CMs 1077688 Specdb::CMs 1077690 Specdb::CMs 1077692 Specdb::CMs 1077693 Specdb::CMs 1077695 Specdb::CMs 1077697 Specdb::CMs 1077699 Specdb::CMs 1077700 Specdb::CMs 1077702 Specdb::CMs 1077704 Specdb::CMs 1077706 Specdb::CMs 1077708 Specdb::CMs 1077710 Specdb::NmrOneD 1559 Specdb::NmrOneD 145490 Specdb::NmrOneD 145491 Specdb::NmrOneD 145492 Specdb::NmrOneD 145493 Specdb::NmrOneD 145494 Specdb::NmrOneD 145495 Specdb::NmrOneD 145496 Specdb::NmrOneD 145497 Specdb::NmrOneD 145498 Specdb::NmrOneD 145499 Specdb::NmrOneD 145500 Specdb::NmrOneD 145501 Specdb::NmrOneD 145502 Specdb::NmrOneD 145503 Specdb::NmrOneD 145504 Specdb::NmrOneD 145505 Specdb::NmrOneD 145506 Specdb::NmrOneD 145507 Specdb::NmrOneD 145508 Specdb::NmrOneD 145509 Specdb::NmrOneD 166340 Specdb::NmrOneD 166567 Specdb::MsMs 1178 Specdb::MsMs 1179 Specdb::MsMs 1180 Specdb::MsMs 4705 Specdb::MsMs 4706 Specdb::MsMs 4707 Specdb::MsMs 4708 Specdb::MsMs 4709 Specdb::MsMs 180156 Specdb::MsMs 180157 Specdb::MsMs 180158 Specdb::MsMs 182490 Specdb::MsMs 182491 Specdb::MsMs 182492 Specdb::MsMs 437400 Specdb::MsMs 437401 Specdb::MsMs 437402 Specdb::MsMs 437403 Specdb::MsMs 437404 Specdb::MsMs 2257289 Specdb::MsMs 2257308 Specdb::MsMs 2259242 Specdb::MsMs 2259307 Specdb::MsMs 2845508 Specdb::MsMs 2845509 Specdb::NmrTwoD 1501 HMDB00828 93072 84022 C00438 15859 CARBAMYUL-L-ASPARTATE NCD Carbamoyl_aspartic_acid Keseler, I. 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Epub 2004 Sep 16. 15375016 http://hmdb.ca/system/metabolites/msds/000/000/746/original/HMDB00828.pdf?1358463474 Dihydroorotase P05020 PYRC_ECOLI pyrC http://ecmdb.ca/proteins/P05020.xml Aspartate carbamoyltransferase catalytic chain P0A786 PYRB_ECOLI pyrB http://ecmdb.ca/proteins/P0A786.xml Aspartate carbamoyltransferase regulatory chain P0A7F3 PYRI_ECOLI pyrI http://ecmdb.ca/proteins/P0A7F3.xml L-Aspartic acid + Carbamoylphosphate <> Ureidosuccinic acid + Hydrogen ion + Phosphate R01397 ASPCARBTRANS-RXN 4,5-Dihydroorotic acid + Water <> Ureidosuccinic acid + Hydrogen ion R01993 DIHYDROOROT-RXN Carbamoylphosphate + L-Aspartic acid <> Phosphate + Ureidosuccinic acid R01397 4,5-Dihydroorotic acid + Water <> Ureidosuccinic acid R01993 L-Aspartic acid + Carbamoylphosphate > Hydrogen ion + Ureidosuccinic acid + Phosphate ASPCARBTRANS-RXN Carbamoylphosphate + L-Aspartic acid > Inorganic phosphate + Ureidosuccinic acid (S)-dihydroorotate + Water > Ureidosuccinic acid L-Aspartic acid + Carbamoylphosphate <> Ureidosuccinic acid + Hydrogen ion + Phosphate 4 4,5-Dihydroorotic acid + Water <> Ureidosuccinic acid + Hydrogen ion L-Aspartic acid + Carbamoylphosphate <> Ureidosuccinic acid + Hydrogen ion + Phosphate Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L glucose Shake flask and filter culture 590.0 uM 0.0 37 oC K12 NCM3722 Mid-Log Phase 2360000 0 Bennett, B. D., Kimball, E. H., Gao, M., Osterhout, R., Van Dien, S. J., Rabinowitz, J. D. (2009). "Absolute metabolite concentrations and implied enzyme active site occupancy in Escherichia coli." Nat Chem Biol 5:593-599. 19561621 Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L glycerol Shake flask and filter culture 90.2 uM 0.0 37 oC K12 NCM3722 Mid-Log Phase 360800 0 Bennett, B. D., Kimball, E. H., Gao, M., Osterhout, R., Van Dien, S. J., Rabinowitz, J. D. (2009). "Absolute metabolite concentrations and implied enzyme active site occupancy in Escherichia coli." Nat Chem Biol 5:593-599. 19561621 Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L acetate Shake flask and filter culture 26.6 uM 0.0 37 oC K12 NCM3722 Mid-Log Phase 106400 0 Bennett, B. D., Kimball, E. H., Gao, M., Osterhout, R., Van Dien, S. J., Rabinowitz, J. D. (2009). "Absolute metabolite concentrations and implied enzyme active site occupancy in Escherichia coli." Nat Chem Biol 5:593-599. 19561621 48 mM Na2HPO4, 22 mM KH2PO4, 10 mM NaCl, 45 mM (NH4)2SO4, supplemented with 1 mM MgSO4, 1 mg/l thiamine·HCl, 5.6 mg/l CaCl2, 8 mg/l FeCl3, 1 mg/l MnCl2·4H2O, 1.7 mg/l ZnCl2, 0.43 mg/l CuCl2·2H2O, 0.6 mg/l CoCl2·2H2O and 0.6 mg/l Na2MoO4·2H2O. 4 g/L Gluco Bioreactor, pH controlled, O2 and CO2 controlled, dilution rate: 0.2/h 562.0 uM 0.0 37 oC BW25113 Stationary Phase, glucose limited 2248000 0 Ishii, N., Nakahigashi, K., Baba, T., Robert, M., Soga, T., Kanai, A., Hirasawa, T., Naba, M., Hirai, K., Hoque, A., Ho, P. Y., Kakazu, Y., Sugawara, K., Igarashi, S., Harada, S., Masuda, T., Sugiyama, N., Togashi, T., Hasegawa, M., Takai, Y., Yugi, K., Arakawa, K., Iwata, N., Toya, Y., Nakayama, Y., Nishioka, T., Shimizu, K., Mori, H., Tomita, M. (2007). "Multiple high-throughput analyses monitor the response of E. coli to perturbations." Science 316:593-597. 17379776