2.0 2012-05-31 13:55:05 -0600 2015-06-03 15:54:13 -0600 ECMDB02031 M2MDB000430 Ureidoisobutyric acid Beta-ureidoisobutyrate is an intermediate of pyrimidine metabolism. It is converted from and to dihydrothymine by d-phenylhydantoinase. (KEGG) 3-Carbamoylamino-2-methylpropanoate 3-Carbamoylamino-2-methylpropanoic acid 3-Ureidoisobutyrate 3-Ureidoisobutyric acid <i>N</i>-carbamyl-&beta;-aminoisobutyrate <i>N</i>-carbamyl-&beta;-aminoisobutyric acid b-Uba b-Ureidoisobutyrate b-Ureidoisobutyric acid Beta-Uba Beta-Ureidoisobutyrate Beta-Ureidoisobutyric acid DL-b-Ureidoisobutyrate DL-b-Ureidoisobutyric acid DL-beta-Ureidoisobutyrate DL-beta-Ureidoisobutyric acid DL-β-Ureidoisobutyrate DL-β-Ureidoisobutyric acid n-Carbamyl-&beta;-aminoisobutyrate n-Carbamyl-&beta;-aminoisobutyric acid N-Carbamyl-amino isobutyrate N-Carbamyl-amino isobutyric acid N-Carbamyl-b-aminoisobutyrate N-Carbamyl-b-aminoisobutyric acid N-Carbamyl-beta-aminoisobutyrate N-Carbamyl-beta-aminoisobutyric acid N-Carbamyl-β-aminoisobutyrate N-Carbamyl-β-aminoisobutyric acid Ureidoisobutyrate β-Uba β-Ureidoisobutyrate β-Ureidoisobutyric acid C5H10N2O3 146.1445 146.069142196 3-(carbamoylamino)-2-methylpropanoic acid β-ureidoisobutyric acid 2905-86-4 CC(CNC(N)=O)C(O)=O InChI=1S/C5H10N2O3/c1-3(4(8)9)2-7-5(6)10/h3H,2H2,1H3,(H,8,9)(H3,6,7,10) PHENTZNALBMCQD-UHFFFAOYSA-N Solid Cytoplasm Periplasm logp -0.86 ALOGPS logs -0.50 ALOGPS solubility 4.61e+01 g/l ALOGPS logp -0.88 ChemAxon pka_strongest_acidic 4.32 ChemAxon pka_strongest_basic -1.8 ChemAxon iupac 3-(carbamoylamino)-2-methylpropanoic acid ChemAxon average_mass 146.1445 ChemAxon mono_mass 146.069142196 ChemAxon smiles CC(CNC(N)=O)C(O)=O ChemAxon formula C5H10N2O3 ChemAxon inchi InChI=1S/C5H10N2O3/c1-3(4(8)9)2-7-5(6)10/h3H,2H2,1H3,(H,8,9)(H3,6,7,10) ChemAxon inchikey PHENTZNALBMCQD-UHFFFAOYSA-N ChemAxon polar_surface_area 92.42 ChemAxon refractivity 33.4 ChemAxon polarizability 13.81 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 3 ChemAxon donor_count 3 ChemAxon physiological_charge -1 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 Specdb::CMs 16905 Specdb::CMs 38234 Specdb::NmrOneD 332022 Specdb::NmrOneD 332023 Specdb::NmrOneD 332024 Specdb::NmrOneD 332025 Specdb::NmrOneD 332026 Specdb::NmrOneD 332027 Specdb::NmrOneD 332028 Specdb::NmrOneD 332029 Specdb::NmrOneD 332030 Specdb::NmrOneD 332031 Specdb::NmrOneD 332032 Specdb::NmrOneD 332033 Specdb::NmrOneD 332034 Specdb::NmrOneD 332035 Specdb::NmrOneD 332036 Specdb::NmrOneD 332037 Specdb::NmrOneD 332038 Specdb::NmrOneD 332039 Specdb::NmrOneD 332040 Specdb::NmrOneD 332041 Specdb::MsMs 24959 Specdb::MsMs 24960 Specdb::MsMs 24961 Specdb::MsMs 31517 Specdb::MsMs 31518 Specdb::MsMs 31519 Specdb::MsMs 3608071 Specdb::MsMs 3608072 Specdb::MsMs 3608073 Specdb::MsMs 3608074 Specdb::MsMs 3608075 Specdb::MsMs 3608076 HMDB02031 160663 141172 C05100 1670 3-UREIDO-ISOBUTYRATE 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 Hofmann U, Schwab M, Seefried S, Marx C, Zanger UM, Eichelbaum M, Murdter TE: Sensitive method for the quantification of urinary pyrimidine metabolites in healthy adults by gas chromatography-tandem mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Jul 5;791(1-2):371-80. 12798197 Ohse M, Matsuo M, Ishida A, Kuhara T: Screening and diagnosis of beta-ureidopropionase deficiency by gas chromatographic/mass spectrometric analysis of urine. J Mass Spectrom. 2002 Sep;37(9):954-62. 12271438 Evans, W. R.; Tsai, Chi Shiun; Axelrod, Bernard. Origin of b-aminoisobutyric acid in iris. Nature (London, United Kingdom) (1961), 190 809. D-phenylhydantoinase Q46806 PHYDA_ECOLI hyuA http://ecmdb.ca/proteins/Q46806.xml Dihydrothymine + Water <> Ureidoisobutyric acid R03055