2.0 2012-07-30 14:55:16 -0600 2015-06-03 17:21:06 -0600 ECMDB21299 M2MDB001703 Ureidoacrylate peracid Ureidoacrylate peracid is a member of the chemical class known as Enones. These are compounds containing the enone functional group, with the structure RC(=O)CR'. (2Z)-3-(carbamoylamino)prop-2-eneperoxoate (2Z)-3-(carbamoylamino)prop-2-eneperoxoic acid (Z)-3-Ureidoacrylate peracid (Z)-3-Ureidoacrylic acid peracid Peroxy ureidoacrylate Peroxy ureidoacrylic acid Ureidoacrylate peracid Ureidoacrylic acid peracid Ureidoperacrylate Ureidoperacrylic acid C4H6N2O4 146.1014 146.03275669 (2Z)-3-(carbamoylamino)prop-2-eneperoxoic acid ureidoacrylate peracid NC(=O)N\C=C/C(=O)OO InChI=1S/C4H6N2O4/c5-4(8)6-2-1-3(7)10-9/h1-2,9H,(H3,5,6,8)/b2-1- AJFKXWQDHFYKFK-UPHRSURJSA-N Cytosol logp -1.17 ALOGPS logs -1.14 ALOGPS solubility 1.06e+01 g/l ALOGPS logp -1.1 ChemAxon pka_strongest_acidic 7.39 ChemAxon pka_strongest_basic -6.1 ChemAxon iupac (2Z)-3-(carbamoylamino)prop-2-eneperoxoic acid ChemAxon average_mass 146.1014 ChemAxon mono_mass 146.03275669 ChemAxon smiles NC(=O)N\C=C/C(=O)OO ChemAxon formula C4H6N2O4 ChemAxon inchi InChI=1S/C4H6N2O4/c5-4(8)6-2-1-3(7)10-9/h1-2,9H,(H3,5,6,8)/b2-1- ChemAxon inchikey AJFKXWQDHFYKFK-UPHRSURJSA-N ChemAxon polar_surface_area 101.65 ChemAxon refractivity 30.68 ChemAxon polarizability 12.12 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 3 ChemAxon donor_count 3 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon 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 Uracil degradation III PW002026 Metabolic uracil degradation III PWY0-1471 Specdb::CMs 1088473 Specdb::MsMs 26498 Specdb::MsMs 26499 Specdb::MsMs 26500 Specdb::MsMs 33056 Specdb::MsMs 33057 Specdb::MsMs 33058 46173244 26331742 C20231 59889 CPD0-2338 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 Putative flavin reductase rutF P75893 RUTF_ECOLI rutF http://ecmdb.ca/proteins/P75893.xml Putative monooxygenase rutA P75898 RUTA_ECOLI rutA http://ecmdb.ca/proteins/P75898.xml Putative isochorismatase family protein rutB P75897 RUTB_ECOLI rutB http://ecmdb.ca/proteins/P75897.xml Hydrogen ion + NADH + Oxygen + Uracil > NAD + Ureidoacrylate peracid Water + Ureidoacrylate peracid > Carbamic acid + Hydrogen ion + Peroxyaminoacrylate R09947 RXN0-6460 Uracil + FMNH + Oxygen <> Ureidoacrylate peracid + Flavin Mononucleotide R09936 RXN0-6444 Ureidoacrylate peracid + Water <> Peroxyaminoacrylate + Carbamic acid R09947 Ureidoacrylate peracid + NADH > 3-ureidoacrylate + NAD + Water RXN0-6450 Uracil + Oxygen + FMNH > Hydrogen ion + Ureidoacrylate peracid + Flavin Mononucleotide RXN0-6444 Uracil + FMNH(2) + Oxygen > Ureidoacrylate peracid + Flavin Mononucleotide + Water Ureidoacrylate peracid + Water > Peroxyaminoacrylate + Ammonia Ureidoacrylate peracid + Water + Carbamic acid + (Z)-2-Methyl-ureidoacrylate peracid <> Peroxyaminoacrylate + Carbon dioxide + Ammonia + (Z)-2-Methyl-peroxyaminoacrylate R09948 Uracil + FMNH + Oxygen + Thymine <> Ureidoacrylate peracid + Flavin Mononucleotide + (Z)-2-Methyl-ureidoacrylate peracid R09936 Uracil + FMNH2 + Oxygen > Ureidoacrylate peracid + Flavin Mononucleotide + Hydrogen ion + Peroxyaminoacrylate PW_R005905 Ureidoacrylate peracid + Water > Peroxyaminoacrylate + Carbamic acid + Hydrogen ion + 3-Aminoacrylate PW_R005906