2.0 2012-05-31 14:07:23 -0600 2015-09-13 12:56:14 -0600 ECMDB04172 M2MDB000652 Urea Urea is the principal end product of protein catabolism. Urea is formed in a cyclic pathway known simply as the urea cycle. In this cycle, amino groups donated by ammonia and L-aspartate are converted to urea. Urea is essentially a waste product; it has no physiological function. Alphadrate Alphadric acid Aqua care Aqua care HP Aquacare HP Aquadrate Aquadric acid ARF B-I-k Basodexan Beta-I-k Breathtek ubt for h-pylori Bromisovalum Bubber shet Calmurid Calmurid HC Carbaderm Carbamex 330mgms Carbamide Carbamide resin Carbamimate Carbamimic acid Carbamimidate Carbamimidic acid Carbonyl diamide Carbonyl diamine Carbonyldiamide Carbonyldiamine Carmol Carmol 40 Carmol HC Caswell No. 902 Dermaflex 20 Urea Cream 20% Dermaflex Crm 10% Dermal therapy-finger care Dermal therapy-hand elbow and knee cream Dermal therapy-heel care Elaqua XX Eucerin Lotion 10% D'uree Harnstoff Harnstoff [german] Helicosol Hyanit Isourea Keratinamin Keratinamin kowa Lotion Mocovina Mocovina [czech] Murine ear wax removal system/murine ear drops Nutraplus Onychomal Optigen 1200 Panafil Pastaron Pastaron (TN) Pastaron 10 Pastaron 20 Pastaron 20 soft Pastaron soft Polyurea Prespersion 75 urea Pseudourea Pseudourea [MeSH: pseudourea] Pylori-chek breath test Rubinol ST 010 Simply botanical sensations healing hands Supercel 3000 Superprill U-cort Ultra mide Ultra Mide 25 URE Urea (JP15/USP) Urea ammonium nitrate solution Urea ammonium nitric acid solution Urea homopolymer Urea perhydrate Urea perhydric acid Urea solution Urea-13C Ureacin-10 lotion Ureacin-20 Ureacin-40 Creme Ureaphil Urederm Cream 10% Uree 20 Cream Uremol 10 Cream 10% Uremol 10 Lotion 10% Uremol 20 Cream 20% Ureophil Urepeal Urepeal l Urepearl Urevert Urisec 22% Crm Urisec Lotion 12% Varioform II β-I-K CH4N2O 60.0553 60.03236276 urea urea 57-13-6 NC(N)=O InChI=1S/CH4N2O/c2-1(3)4/h(H4,2,3,4) XSQUKJJJFZCRTK-UHFFFAOYSA-N Solid Cytosol Extra-organism Periplasm logp -1.78 ALOGPS logs 0.84 ALOGPS solubility 4.12e+02 g/l ALOGPS melting_point 132 oC logp -1.4 ChemAxon pka_strongest_acidic 15.73 ChemAxon pka_strongest_basic -2.4 ChemAxon iupac urea ChemAxon average_mass 60.0553 ChemAxon mono_mass 60.03236276 ChemAxon smiles NC(N)=O ChemAxon formula CH4N2O ChemAxon inchi InChI=1S/CH4N2O/c2-1(3)4/h(H4,2,3,4) ChemAxon inchikey XSQUKJJJFZCRTK-UHFFFAOYSA-N ChemAxon polar_surface_area 69.11 ChemAxon refractivity 13.14 ChemAxon polarizability 5.1 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 1 ChemAxon donor_count 2 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Arginine and proline metabolism ec00330 Purine metabolism ec00230 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 Microbial metabolism in diverse environments ec01120 ABC transporters ec02010 Metabolic pathways eco01100 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 glycolate and glyoxylate degradation Glycolic acid is introduced into the cytoplasm through either a glycolate / lactate:H+ symporter or a acetate / glycolate transporter. Once inside, glycolic acid reacts with an oxidized electron-transfer flavoprotein through a glycolate oxidase resulting in a reduced acceptor and glyoxylic acid. Glyoxylic acid can also be obtained from the introduction of glyoxylic acid. It can also be obtained from the metabolism of (S)-allantoin. S-allantoin is introduced into the cytoplasm through a purine and pyrimidine transporter(allantoin specific). Once inside, the compound reacts with water through a allantoinase resulting in hydrogen ion and allantoic acid. Allantoic acid then reacts with water and hydrogen ion through a allantoate amidohydrolase resulting in a carbon dioxide, ammonium and S-ureidoglycine. The latter compound reacts with water through a S-ureidoglycine aminohydrolase resulting in ammonium and S-ureidoglycolic acid which in turn reacts with a Ureidoglycolate lyase resulting in urea and glyoxylic acid. Glyoxylic acid can either be metabolized into L-malic acid by a reaction with acetyl-CoA and Water through a malate synthase G which also releases hydrogen ion and Coenzyme A. L-malic acid is then incorporated into the TCA cycle. Glyoxylic acid can also be metabolized by glyoxylate carboligase, releasing a carbon dioxide and tartronate semialdehyde. The latter compound is then reduced by an NADH driven tartronate semialdehyde reductase 2 resulting in glyceric acid. Glyceric acid is phosphorylated by a glycerate kinase 2 resulting in a 3-phosphoglyceric acid. This compound is then integrated into various other pathways: cysteine biosynthesis, serine biosynthesis and glycolysis and pyruvate dehydrogenase. PW000827 Metabolic allantoin degradation to glyoxylate III PWY-5705 arginine degradation III (arginine decarboxylase/agmatinase pathway) PWY0-823 putrescine biosynthesis I PWY-40 Specdb::CMs 523 Specdb::CMs 989 Specdb::CMs 2923 Specdb::CMs 29896 Specdb::CMs 30707 Specdb::CMs 31117 Specdb::CMs 31908 Specdb::CMs 137743 Specdb::CMs 145477 Specdb::EiMs 749 Specdb::NmrOneD 1227 Specdb::NmrOneD 1317 Specdb::NmrOneD 2485 Specdb::NmrOneD 166458 Specdb::NmrOneD 166560 Specdb::MsMs 498 Specdb::MsMs 499 Specdb::MsMs 500 Specdb::MsMs 21287 Specdb::MsMs 21288 Specdb::MsMs 21289 Specdb::MsMs 22838 Specdb::MsMs 22839 Specdb::MsMs 22840 Specdb::MsMs 447325 Specdb::MsMs 2246317 Specdb::MsMs 2247952 Specdb::MsMs 2751685 Specdb::MsMs 2751686 Specdb::MsMs 2751687 Specdb::MsMs 2930421 Specdb::MsMs 2930422 Specdb::MsMs 2930423 HMDB00294 1176 1143 C00086 16199 UREA URE Urea Keseler, I. 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(1942), 21 25-7. http://hmdb.ca/system/metabolites/msds/000/000/215/original/HMDB00294.pdf?1358896163 Agmatinase P60651 SPEB_ECOLI speB http://ecmdb.ca/proteins/P60651.xml Ureidoglycolate hydrolase P77731 ALLA_ECOLI allA http://ecmdb.ca/proteins/P77731.xml Outer membrane protein N P77747 OMPN_ECOLI ompN http://ecmdb.ca/proteins/P77747.xml Outer membrane pore protein E P02932 PHOE_ECOLI phoE http://ecmdb.ca/proteins/P02932.xml Glycerol uptake facilitator protein P0AER0 GLPF_ECOLI glpF http://ecmdb.ca/proteins/P0AER0.xml Outer membrane protein F P02931 OMPF_ECOLI ompF http://ecmdb.ca/proteins/P02931.xml Outer membrane protein C P06996 OMPC_ECOLI ompC http://ecmdb.ca/proteins/P06996.xml Agmatine + Water <> Putrescine + Urea + Ethylenediamine R01157 AGMATIN-RXN Agmatine + Water <> Putrescine + Urea R01157 Water + Agmatine > Urea + Putrescine AGMATIN-RXN (S)-Ureidoglycolic acid > Urea + Glyoxylic acid UREIDOGLYCOLATE-LYASE-RXN (S)-Ureidoglycolic acid <> Glyoxylic acid + Urea R00776