2.0 2012-05-31 13:47:13 -0600 2015-06-03 15:53:49 -0600 ECMDB01191 M2MDB000290 Deoxyuridine triphosphate Deoxyuridine triphosphate is an intermediate in the metabolism of Pyrimidine. It is a substrate for Inosine triphosphate pyrophosphatase, Uridine-cytidine kinase 1, Nucleoside diphosphate kinase 3, Nucleoside diphosphate kinase B, Nucleoside diphosphate kinase 6, Nucleoside diphosphate kinase homolog 5, Nucleoside diphosphate kinase A and Nucleoside diphosphate kinase 7. 2'-Deoxyuridine 5'-triphosphate 2'-Deoxyuridine 5'-triphosphoric acid 2'-Deoxyuridine-5'-triphosphate 2'-Deoxyuridine-5'-triphosphate = dUTP 2'-Deoxyuridine-5'-triphosphorate 2'-Deoxyuridine-5'-triphosphorate = dUTP 2'-Deoxyuridine-5'-triphosphoric acid 2'-Deoxyuridine-5'-triphosphoric acid = dUTP Deoxy-UTP Deoxyuridine triphosphate Deoxyuridine triphosphoric acid Deoxyuridine-5'-Triphosphate Deoxyuridine-5'-triphosphoric acid Deoxyuridine-triphosphate Deoxyuridine-triphosphoric acid DUTP C9H15N2O14P3 468.1417 467.973612734 ({[({[(2R,3S,5R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3-hydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphonic acid dUTP 1173-82-6 O[C@H]1C[C@@H](O[C@@H]1COP(O)(=O)OP(O)(=O)OP(O)(O)=O)N1C=CC(=O)NC1=O InChI=1S/C9H15N2O14P3/c12-5-3-8(11-2-1-7(13)10-9(11)14)23-6(5)4-22-27(18,19)25-28(20,21)24-26(15,16)17/h1-2,5-6,8,12H,3-4H2,(H,18,19)(H,20,21)(H,10,13,14)(H2,15,16,17)/t5-,6+,8+/m0/s1 AHCYMLUZIRLXAA-SHYZEUOFSA-N Solid Cytosol logp -0.12 ALOGPS logs -1.73 ALOGPS solubility 8.63e+00 g/l ALOGPS logp -2.5 ChemAxon pka_strongest_acidic 0.9 ChemAxon pka_strongest_basic -3.2 ChemAxon iupac ({[({[(2R,3S,5R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3-hydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphonic acid ChemAxon average_mass 468.1417 ChemAxon mono_mass 467.973612734 ChemAxon smiles O[C@H]1C[C@@H](O[C@@H]1COP(O)(=O)OP(O)(=O)OP(O)(O)=O)N1C=CC(=O)NC1=O ChemAxon formula C9H15N2O14P3 ChemAxon inchi InChI=1S/C9H15N2O14P3/c12-5-3-8(11-2-1-7(13)10-9(11)14)23-6(5)4-22-27(18,19)25-28(20,21)24-26(15,16)17/h1-2,5-6,8,12H,3-4H2,(H,18,19)(H,20,21)(H,10,13,14)(H2,15,16,17)/t5-,6+,8+/m0/s1 ChemAxon inchikey AHCYMLUZIRLXAA-SHYZEUOFSA-N ChemAxon polar_surface_area 238.69 ChemAxon refractivity 83.67 ChemAxon polarizability 34.62 ChemAxon rotatable_bond_count 8 ChemAxon acceptor_count 11 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 Metabolic pathways eco01100 pyrimidine deoxyribonucleotides <i>de novo</i> biosynthesis I PWY0-166 Specdb::CMs 14787 Specdb::CMs 37967 Specdb::CMs 167680 Specdb::NmrOneD 146770 Specdb::NmrOneD 146771 Specdb::NmrOneD 146772 Specdb::NmrOneD 146773 Specdb::NmrOneD 146774 Specdb::NmrOneD 146775 Specdb::NmrOneD 146776 Specdb::NmrOneD 146777 Specdb::NmrOneD 146778 Specdb::NmrOneD 146779 Specdb::NmrOneD 146780 Specdb::NmrOneD 146781 Specdb::NmrOneD 146782 Specdb::NmrOneD 146783 Specdb::NmrOneD 146784 Specdb::NmrOneD 146785 Specdb::NmrOneD 146786 Specdb::NmrOneD 146787 Specdb::NmrOneD 146788 Specdb::NmrOneD 146789 Specdb::MsMs 28628 Specdb::MsMs 28629 Specdb::MsMs 28630 Specdb::MsMs 35186 Specdb::MsMs 35187 Specdb::MsMs 35188 Specdb::MsMs 2244630 Specdb::MsMs 2245475 Specdb::MsMs 2246708 Specdb::MsMs 2247591 Specdb::MsMs 2248677 Specdb::MsMs 2249691 Specdb::MsMs 2250741 Specdb::MsMs 2251667 Specdb::MsMs 2809841 Specdb::MsMs 2809842 Specdb::MsMs 2809843 Specdb::MsMs 2899314 Specdb::MsMs 2899315 Specdb::MsMs 2899316 HMDB01191 689 58580 C00460 17625 DUTP DUT 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 Oosterhuis GJ, Mulder AB, Kalsbeek-Batenburg E, Lambalk CB, Schoemaker J, Vermes I: Measuring apoptosis in human spermatozoa: a biological assay for semen quality? Fertil Steril. 2000 Aug;74(2):245-50. 10927039 Lee AY, Youm YH, Kim NH, Yang H, Choi WI: Keratinocytes in the depigmented epidermis of vitiligo are more vulnerable to trauma (suction) than keratinocytes in the normally pigmented epidermis, resulting in their apoptosis. Br J Dermatol. 2004 Nov;151(5):995-1003. 15541077 Ge YF, Huang YF, Zhang GY, Wang XH, Xu JP: Studies on apoptosis of spermatogenic cells in normal fertile men treated with supraphysiological doses of testosterone undecanoate. Asian J Androl. 1999 Sep;1(3):155-8. 11250785 Gilhar A, Ullmann Y, Karry R, Shalaginov R, Assy B, Serafimovich S, Kalish RS: Ageing of human epidermis: the role of apoptosis, Fas and telomerase. Br J Dermatol. 2004 Jan;150(1):56-63. 14746617 Igarashi T, Brown CR, Byrum RA, Nishimura Y, Endo Y, Plishka RJ, Buckler C, Buckler-White A, Miller G, Hirsch VM, Martin MA: Rapid and irreversible CD4+ T-cell depletion induced by the highly pathogenic simian/human immunodeficiency virus SHIV(DH12R) is systemic and synchronous. J Virol. 2002 Jan;76(1):379-91. 11739702 Russell J, O'Donoghue JA, Finn R, Koziorowski J, Ruan S, Humm JL, Ling CC: Iodination of annexin V for imaging apoptosis. J Nucl Med. 2002 May;43(5):671-7. 11994533 Lamperti C, Naini AB, Lucchini V, Prelle A, Bresolin N, Moggio M, Sciacco M, Kaufmann P, DiMauro S: Muscle coenzyme Q10 level in statin-related myopathy. Arch Neurol. 2005 Nov;62(11):1709-12. 16286544 Deoxyuridine 5'-triphosphate nucleotidohydrolase P06968 DUT_ECOLI dut http://ecmdb.ca/proteins/P06968.xml Nucleoside diphosphate kinase P0A763 NDK_ECOLI ndk http://ecmdb.ca/proteins/P0A763.xml Uridine kinase P0A8F4 URK_ECOLI udk http://ecmdb.ca/proteins/P0A8F4.xml Anaerobic ribonucleoside-triphosphate reductase-activating protein P0A9N8 NRDG_ECOLI nrdG http://ecmdb.ca/proteins/P0A9N8.xml Protein mazG P0AEY3 MAZG_ECOLI mazG http://ecmdb.ca/proteins/P0AEY3.xml Deoxycytidine triphosphate deaminase P28248 DCD_ECOLI dcd http://ecmdb.ca/proteins/P28248.xml Ferredoxin--NADP reductase P28861 FENR_ECOLI fpr http://ecmdb.ca/proteins/P28861.xml Anaerobic ribonucleoside-triphosphate reductase P28903 NRDD_ECOLI nrdD http://ecmdb.ca/proteins/P28903.xml Nucleoside triphosphatase nudI P52006 NUDI_ECOLI nudI http://ecmdb.ca/proteins/P52006.xml Nucleoside-triphosphatase rdgB P52061 RDGB_ECOLI rdgB http://ecmdb.ca/proteins/P52061.xml Adenylate kinase P69441 KAD_ECOLI adk http://ecmdb.ca/proteins/P69441.xml Flavodoxin-2 P0ABY4 FLAW_ECOLI fldB http://ecmdb.ca/proteins/P0ABY4.xml Flavodoxin-1 P61949 FLAV_ECOLI fldA http://ecmdb.ca/proteins/P61949.xml Nucleoside diphosphate kinase P0A763 NDK_ECOLI ndk http://ecmdb.ca/proteins/P0A763.xml 2 Flavodoxin reduced + 2 Hydrogen ion + Uridine triphosphate > Deoxyuridine triphosphate +2 flavodoxin semi oxidized + Water Adenosine triphosphate + dUDP <> ADP + Deoxyuridine triphosphate R02331 DUDPKIN-RXN Deoxyuridine triphosphate + Water <> dUMP + Hydrogen ion + Pyrophosphate R02100 DUTP-PYROP-RXN dCTP + Hydrogen ion + Water > Deoxyuridine triphosphate + Ammonium Deoxyuridine triphosphate + Thioredoxin disulfide + Water <> Uridine triphosphate + Thioredoxin R02023 Deoxyuridine triphosphate + Water <> dUMP + Pyrophosphate R02100 dCTP + Water <> Deoxyuridine triphosphate + Ammonia R02325 Adenosine triphosphate + dUDP <> ADP + Deoxyuridine triphosphate R02331 Deoxyuridine triphosphate + Uridine <> dUDP + Uridine 5'-monophosphate R02332 Deoxyuridine triphosphate + Cytidine <> dUDP + Cytidine monophosphate R02372 Water + dCTP > Ammonia + Deoxyuridine triphosphate R02325 DCTP-DEAM-RXN dUDP + Adenosine triphosphate > Deoxyuridine triphosphate + ADP DUDPKIN-RXN Deoxyuridine triphosphate + Water > Hydrogen ion + dUMP + Pyrophosphate DUTP-PYROP-RXN Deoxyuridine triphosphate + Water > dUMP + Pyrophosphate dUDP + Adenosine triphosphate + dUDP > Adenosine diphosphate + Deoxyuridine triphosphate + ADP PW_R003538 Uridine triphosphate + a reduced flavodoxin + Uridine triphosphate > Water + an oxidized flavodoxin + Deoxyuridine triphosphate PW_R003543 Deoxyuridine triphosphate + Water > Phosphate + Hydrogen ion + dUMP PW_R003539 Deoxyuridine triphosphate + Water <> dUMP + Hydrogen ion + Pyrophosphate Deoxyuridine triphosphate + Water <> dUMP + Hydrogen ion + Pyrophosphate