2.0 2012-05-31 10:23:59 -0600 2015-06-03 15:53:24 -0600 ECMDB00218 M2MDB000090 Orotidylic acid Orotidylic acid (OMP), is a pyrimidine nucleotide which is the last intermediate in the biosynthesis of uridine monophosphate. Decarboxylation by Orotidylate decarboxylase affords Uridine 5'-phosphate which is the route to Uridine and its derivatives de novo and consequently one of the most important processes in nucleic acid synthesis (Dictionary of Organic Compounds). In E. coli, the enzyme UMP synthase converts OMP into uridine 5'- monophosphate. If UMP synthase is defective, orotic aciduria can result. (Wikipedia) 1,2,3,6-Tetrahydro-2,6-dioxo-3-(5-O-phosphono-b-D-ribofuranosyl)-4-Pyrimidinecarboxylate 1,2,3,6-Tetrahydro-2,6-dioxo-3-(5-O-phosphono-b-D-ribofuranosyl)-4-Pyrimidinecarboxylic acid 1,2,3,6-tetrahydro-2,6-dioxo-3-(5-O-phosphono-b-delta-Ribofuranosyl)-4-pyrimidinecarboxylate 1,2,3,6-tetrahydro-2,6-dioxo-3-(5-O-phosphono-b-delta-Ribofuranosyl)-4-pyrimidinecarboxylic acid 1,2,3,6-tetrahydro-2,6-dioxo-3-(5-O-phosphono-b-δ-Ribofuranosyl)-4-pyrimidinecarboxylate 1,2,3,6-tetrahydro-2,6-dioxo-3-(5-O-phosphono-b-δ-Ribofuranosyl)-4-pyrimidinecarboxylic acid 1,2,3,6-Tetrahydro-2,6-dioxo-3-(5-O-phosphono-beta-delta-ribofuranosyl)-4-Pyrimidinecarboxylate 1,2,3,6-Tetrahydro-2,6-dioxo-3-(5-O-phosphono-beta-delta-ribofuranosyl)-4-Pyrimidinecarboxylic acid 1,2,3,6-tetrahydro-2,6-dioxo-3-(5-O-phosphono-β-δ-Ribofuranosyl)-4-pyrimidinecarboxylate 1,2,3,6-tetrahydro-2,6-dioxo-3-(5-O-phosphono-β-δ-Ribofuranosyl)-4-pyrimidinecarboxylic acid 2,6-dioxo-3-(5-O-phosphono-b-D-Ribofuranosyl)-1,2,3,6-tetrahydropyrimidine-4-carboxylate 2,6-dioxo-3-(5-O-phosphono-b-D-Ribofuranosyl)-1,2,3,6-tetrahydropyrimidine-4-carboxylic acid 2,6-dioxo-3-(5-O-phosphono-b-delta-Ribofuranosyl)-1,2,3,6-tetrahydropyrimidine-4-carboxylate 2,6-dioxo-3-(5-O-phosphono-b-delta-Ribofuranosyl)-1,2,3,6-tetrahydropyrimidine-4-carboxylic acid 2,6-dioxo-3-(5-O-phosphono-b-δ-Ribofuranosyl)-1,2,3,6-tetrahydropyrimidine-4-carboxylate 2,6-dioxo-3-(5-O-phosphono-b-δ-Ribofuranosyl)-1,2,3,6-tetrahydropyrimidine-4-carboxylic acid 2,6-Dioxo-3-(5-O-phosphono-beta-D-ribofuranosyl)-1,2,3,6-tetrahydropyrimidine-4-carboxylate 2,6-Dioxo-3-(5-O-phosphono-beta-D-ribofuranosyl)-1,2,3,6-tetrahydropyrimidine-4-carboxylic acid 2,6-Dioxo-3-(5-O-phosphono-beta-delta-ribofuranosyl)-1,2,3,6-tetrahydropyrimidine-4-carboxylate 2,6-Dioxo-3-(5-O-phosphono-beta-delta-ribofuranosyl)-1,2,3,6-tetrahydropyrimidine-4-carboxylic acid 2,6-dioxo-3-(5-O-phosphono-β-D-Ribofuranosyl)-1,2,3,6-tetrahydropyrimidine-4-carboxylate 2,6-dioxo-3-(5-O-phosphono-β-D-Ribofuranosyl)-1,2,3,6-tetrahydropyrimidine-4-carboxylic acid 2,6-dioxo-3-(5-O-phosphono-β-δ-Ribofuranosyl)-1,2,3,6-tetrahydropyrimidine-4-carboxylate 2,6-dioxo-3-(5-O-phosphono-β-δ-Ribofuranosyl)-1,2,3,6-tetrahydropyrimidine-4-carboxylic acid 5'-(Dihydrogen phosphate) 6-carboxy-uridine 5'-(Dihydrogen phosphate) Orotidine 5'-(Dihydrogen phosphoric acid) 6-carboxy-uridine 5'-(Dihydrogen phosphoric acid) orotidine 5'-OMP 5'-Phosphate Orotidine 5'-Phosphoric acid orotidine 5-(Dihydrogen phosphate)orotidine 5-(Dihydrogen phosphoric acid)orotidine 6-Carboxy-5'-uridylate 6-Carboxy-5'-uridylic acid Ometoprim OMP Omp (nucleotide) Orotidine 5'-(dihydrogen phosphate) Orotidine 5'-(dihydrogen phosphoric acid) Orotidine 5'-monophosphate Orotidine 5'-monophosphoric acid Orotidine 5'-phosphate Orotidine 5'-phosphoric acid Orotidine monophosphate Orotidine monophosphoric acid Orotidine-5'-phosphate Orotidine-5'-phosphoric acid Orotidine5'P Orotidylate Orotidylic acid C10H13N2O11P 368.1908 368.02569578 3-[(2R,3R,4S,5R)-3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]-2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylic acid 6-carboxy-5'-uridylic acid 2149-82-8 O[C@H]1[C@@H](O)[C@@H](O[C@@H]1COP(O)(O)=O)N1C(=O)NC(=O)C=C1C(O)=O InChI=1S/C10H13N2O11P/c13-5-1-3(9(16)17)12(10(18)11-5)8-7(15)6(14)4(23-8)2-22-24(19,20)21/h1,4,6-8,14-15H,2H2,(H,16,17)(H,11,13,18)(H2,19,20,21)/t4-,6-,7-,8-/m1/s1 KYOBSHFOBAOFBF-XVFCMESISA-N Solid Cytosol logp -1.67 ALOGPS logs -1.63 ALOGPS solubility 8.61e+00 g/l ALOGPS logp -2.9 ChemAxon pka_strongest_acidic 1.21 ChemAxon pka_strongest_basic -3.7 ChemAxon iupac 3-[(2R,3R,4S,5R)-3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]-2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylic acid ChemAxon average_mass 368.1908 ChemAxon mono_mass 368.02569578 ChemAxon smiles O[C@H]1[C@@H](O)[C@@H](O[C@@H]1COP(O)(O)=O)N1C(=O)NC(=O)C=C1C(O)=O ChemAxon formula C10H13N2O11P ChemAxon inchi InChI=1S/C10H13N2O11P/c13-5-1-3(9(16)17)12(10(18)11-5)8-7(15)6(14)4(23-8)2-22-24(19,20)21/h1,4,6-8,14-15H,2H2,(H,16,17)(H,11,13,18)(H2,19,20,21)/t4-,6-,7-,8-/m1/s1 ChemAxon inchikey KYOBSHFOBAOFBF-XVFCMESISA-N ChemAxon polar_surface_area 203.16 ChemAxon refractivity 70.74 ChemAxon polarizability 29.65 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 10 ChemAxon donor_count 6 ChemAxon physiological_charge -3 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 Drug metabolism - other enzymes ec00983 Metabolic pathways eco01100 uridine-5'-phosphate biosynthesis PWY-5686 Specdb::CMs 19928 Specdb::CMs 37366 Specdb::CMs 153297 Specdb::CMs 1054946 Specdb::CMs 1054948 Specdb::CMs 1054950 Specdb::CMs 1054952 Specdb::CMs 1054954 Specdb::CMs 1054956 Specdb::CMs 1054958 Specdb::CMs 1054960 Specdb::CMs 1054962 Specdb::CMs 1054964 Specdb::CMs 1054965 Specdb::CMs 1054968 Specdb::CMs 1054969 Specdb::CMs 1054971 Specdb::CMs 1054973 Specdb::CMs 1054975 Specdb::CMs 1054977 Specdb::CMs 1054979 Specdb::CMs 1054980 Specdb::CMs 1054982 Specdb::CMs 1054984 Specdb::CMs 1054986 Specdb::NmrOneD 143010 Specdb::NmrOneD 143011 Specdb::NmrOneD 143012 Specdb::NmrOneD 143013 Specdb::NmrOneD 143014 Specdb::NmrOneD 143015 Specdb::NmrOneD 143016 Specdb::NmrOneD 143017 Specdb::NmrOneD 143018 Specdb::NmrOneD 143019 Specdb::NmrOneD 143020 Specdb::NmrOneD 143021 Specdb::NmrOneD 143022 Specdb::NmrOneD 143023 Specdb::NmrOneD 143024 Specdb::NmrOneD 143025 Specdb::NmrOneD 143026 Specdb::NmrOneD 143027 Specdb::NmrOneD 143028 Specdb::NmrOneD 143029 Specdb::MsMs 27008 Specdb::MsMs 27009 Specdb::MsMs 27010 Specdb::MsMs 33566 Specdb::MsMs 33567 Specdb::MsMs 33568 Specdb::MsMs 2826334 Specdb::MsMs 2826335 Specdb::MsMs 2826336 Specdb::MsMs 2855368 Specdb::MsMs 2855369 Specdb::MsMs 2855370 HMDB00218 160617 141140 C01103 15842 OROTIDINE-5-PHOSPHATE OMP Orotidylic acid 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 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 van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. 17765195 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. Nature. 2009 Feb 12;457(7231):910-4. 19212411 Traut TW: Uridine-5'-phosphate synthase: evidence for substrate cycling involving this bifunctional protein. Arch Biochem Biophys. 1989 Jan;268(1):108-15. 2912371 Ueda, Tohru; Yamamoto, Miyako; Yamane, Akira; Imazawa, Masaoki; Inoue, Hideo. Nucleosides and nucleotides. XXIII. Conversion of uridine nucleotides to the 6-cyano derivatives: synthesis of orotidylic acid. Journal of Carbohydrates, Nucleosides, Nuc Orotidine 5'-phosphate decarboxylase P08244 PYRF_ECOLI pyrF http://ecmdb.ca/proteins/P08244.xml Orotate phosphoribosyltransferase P0A7E3 PYRE_ECOLI pyrE http://ecmdb.ca/proteins/P0A7E3.xml Hydrogen ion + Orotidylic acid <> Carbon dioxide + Uridine 5'-monophosphate R00965 OROTPDECARB-RXN Orotidylic acid + Pyrophosphate <> Orotic acid + Phosphoribosyl pyrophosphate R01870 OROPRIBTRANS-RXN Orotidylic acid <> Uridine 5'-monophosphate + Carbon dioxide R00965 Hydrogen ion + Orotidylic acid > Carbon dioxide + Uridine 5'-monophosphate OROTPDECARB-RXN Orotidylic acid + Pyrophosphate > Orotic acid + Phosphoribosyl pyrophosphate Orotidylic acid > Uridine 5'-monophosphate + Carbon dioxide Orotic acid + Phosphoribosyl pyrophosphate > Pyrophosphate + Orotidylic acid PW_R003529 Hydrogen ion + Orotidylic acid <> Carbon dioxide + Uridine 5'-monophosphate Orotidylic acid + Pyrophosphate <> Orotic acid + Phosphoribosyl pyrophosphate Orotidylic acid + Pyrophosphate <> Orotic acid + Phosphoribosyl pyrophosphate