1.0 2016-09-30 22:27:51 UTC 2020-06-04 20:13:25 UTC BMDB0000288 BMDB00288 Uridine 5'-monophosphate Uridine 5'-monophosphate, also known as uridylic acid or UMP, belongs to the class of organic compounds known as pyrimidine ribonucleoside monophosphates. These are pyrimidine ribobucleotides with monophosphate group linked to the ribose moiety. Uridine 5'-monophosphate is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Uridine 5'-monophosphate exists in all living species, ranging from bacteria to humans. Uridine 5'-monophosphate participates in a number of enzymatic reactions, within cattle. In particular, Uridine 5'-monophosphate can be converted into uridine 5'-diphosphate; which is mediated by the enzyme UMP-CMP kinase. In addition, Uridine 5'-monophosphate can be biosynthesized from uridine 5'-diphosphate; which is catalyzed by the enzyme soluble calcium-activated nucleotidase 1. In cattle, uridine 5'-monophosphate is involved in the metabolic pathway called lactose synthesis pathway. 5'-UMP 5'Uridylic acid pU UMP Uridine 5'-(dihydrogen phosphate) Uridine 5'-phosphate Uridine 5'-phosphoric acid Uridine monophosphate URIDINE-5'-monophosphATE Uridylate Uridylic acid 5'Uridylate Uridine 5'-(dihydrogen phosphoric acid) Uridine monophosphoric acid URIDINE-5'-monophosphoric acid Uridine 5'-monophosphoric acid Uridine 5'-phosphorate Uridine mono(dihydrogen phosphate) Uridine phosphate Acids, uridylic monoPhosphate, uridine 5'-monoPhosphate, uridine Uridylic acids Acid, uridylic Uridine 5' monophosphate C9H13N2O9P 324.1813 324.035866536 {[(2R,3S,4R,5R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid uridine monophosphate 58-97-9 O[C@H]1[C@@H](O)[C@@H](O[C@@H]1COP(O)(O)=O)N1C=CC(=O)NC1=O InChI=1S/C9H13N2O9P/c12-5-1-2-11(9(15)10-5)8-7(14)6(13)4(20-8)3-19-21(16,17)18/h1-2,4,6-8,13-14H,3H2,(H,10,12,15)(H2,16,17,18)/t4-,6-,7-,8-/m1/s1 DJJCXFVJDGTHFX-XVFCMESISA-N belongs to the class of organic compounds known as pyrimidine ribonucleoside monophosphates. These are pyrimidine ribobucleotides with monophosphate group linked to the ribose moiety. Organic compounds Nucleosides, nucleotides, and analogues Pyrimidine nucleotides Pyrimidine ribonucleotides Pyrimidine ribonucleoside monophosphates 1,2-diols Azacyclic compounds Glycosylamines Heteroaromatic compounds Hydrocarbon derivatives Hydropyrimidines Lactams Monoalkyl phosphates Monosaccharide phosphates Organic oxides Organonitrogen compounds Organopnictogen compounds Oxacyclic compounds Pentose phosphates Pyrimidones Secondary alcohols Tetrahydrofurans Ureas Vinylogous amides 1,2-diol Alcohol Alkyl phosphate Aromatic heteromonocyclic compound Azacycle Glycosyl compound Heteroaromatic compound Hydrocarbon derivative Hydropyrimidine Lactam Monoalkyl phosphate Monosaccharide Monosaccharide phosphate N-glycosyl compound Organic nitrogen compound Organic oxide Organic oxygen compound Organic phosphoric acid derivative Organoheterocyclic compound Organonitrogen compound Organooxygen compound Organopnictogen compound Oxacycle Pentose monosaccharide Pentose phosphate Pentose-5-phosphate Phosphoric acid ester Pyrimidine Pyrimidine ribonucleoside monophosphate Pyrimidone Secondary alcohol Tetrahydrofuran Urea Vinylogous amide Aromatic heteromonocyclic compounds Ribonucleotides pyrimidine ribonucleoside 5'-monophosphate uridine 5'-phosphate Solid logp -1.76 ALOGPS logs -1.43 ALOGPS logp -2.5 ChemAxon pka_strongest_acidic 1.23 ChemAxon pka_strongest_basic -3.7 ChemAxon iupac {[(2R,3S,4R,5R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid ChemAxon average_mass 324.1813 ChemAxon mono_mass 324.035866536 ChemAxon smiles O[C@H]1[C@@H](O)[C@@H](O[C@@H]1COP(O)(O)=O)N1C=CC(=O)NC1=O ChemAxon formula C9H13N2O9P ChemAxon inchi InChI=1S/C9H13N2O9P/c12-5-1-2-11(9(15)10-5)8-7(14)6(13)4(20-8)3-19-21(16,17)18/h1-2,4,6-8,13-14H,3H2,(H,10,12,15)(H2,16,17,18)/t4-,6-,7-,8-/m1/s1 ChemAxon inchikey DJJCXFVJDGTHFX-XVFCMESISA-N ChemAxon polar_surface_area 165.86 ChemAxon refractivity 63.44 ChemAxon polarizability 26.3 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 8 ChemAxon donor_count 5 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon number_of_rings 2 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon Lactose Synthesis SMP0087229 Pyrimidine Metabolism SMP0087247 Specdb::NmrTwoD 1256 Specdb::MsMs 486 Specdb::MsMs 487 Specdb::MsMs 488 Specdb::MsMs 3927 Specdb::MsMs 180168 Specdb::MsMs 180169 Specdb::MsMs 180170 Specdb::MsMs 182502 Specdb::MsMs 182503 Specdb::MsMs 182504 Specdb::MsMs 439120 Specdb::MsMs 2227065 Specdb::MsMs 2227622 Specdb::MsMs 2229511 Specdb::MsMs 2229984 Specdb::MsMs 2231941 Specdb::MsMs 2232235 Specdb::MsMs 2234305 Specdb::MsMs 2234326 Specdb::MsMs 2234634 Specdb::MsMs 2234663 Specdb::MsMs 2253081 Specdb::MsMs 2253400 Specdb::MsMs 2255153 Specdb::MsMs 2255407 Specdb::CMs 2175 Specdb::CMs 3433 Specdb::CMs 31114 Specdb::CMs 37404 Specdb::CMs 131525 Specdb::CMs 139259 Specdb::CMs 1056849 Specdb::CMs 1056851 Specdb::CMs 1056853 Specdb::CMs 1056855 Specdb::CMs 1056857 Specdb::CMs 1056859 Specdb::CMs 1056861 Specdb::CMs 1056863 Specdb::CMs 1056864 Specdb::CMs 1056865 Specdb::CMs 1056867 Specdb::CMs 1056868 Specdb::CMs 1056870 Specdb::CMs 1056872 Specdb::CMs 1056874 Specdb::CMs 1056876 Specdb::CMs 1056878 Specdb::CMs 1056880 Specdb::CMs 1056882 Specdb::NmrOneD 1313 Specdb::NmrOneD 4744 Specdb::NmrOneD 4745 Specdb::NmrOneD 6442 Specdb::NmrOneD 6443 Specdb::NmrOneD 6444 Specdb::NmrOneD 6445 Specdb::NmrOneD 6446 Specdb::NmrOneD 6447 Specdb::NmrOneD 6448 Specdb::NmrOneD 6449 Specdb::NmrOneD 6450 Specdb::NmrOneD 6451 Specdb::NmrOneD 6452 Specdb::NmrOneD 6453 Specdb::NmrOneD 6454 Specdb::NmrOneD 6455 Specdb::NmrOneD 6456 Specdb::NmrOneD 6457 Specdb::NmrOneD 6458 Specdb::NmrOneD 6459 Specdb::NmrOneD 6460 Specdb::NmrOneD 6461 Liver 58 +/- 31 nmol/g of tissue By NMR Aidin Foroutan, Carolyn Fitzsimmons, Rupasri Mandal, Hamed Piri‐Moghadam, Jiamin Zheng, AnChi Guo, Carin Li, Le Luo Guan and David S. Wishart. The Bovine Metabolome. Metabolites 2020, 10, 233; doi:10.3390/metabo10060233 Liver Metabolomics analysis was performed using GC-MS/LC-MS in multiparous Holstein dairy cows Shahzad K, Lopreiato V, Liang Y, Trevisi E, Osorio JS, Xu C, Loor JJ: Hepatic metabolomics and transcriptomics to study susceptibility to ketosis in response to prepartal nutritional management. J Anim Sci Biotechnol. 2019 Dec 18;10:96. doi: 10.1186/s40104-019-0404-z. eCollection 2019. 31867104 Milk Milk from Friesuan Holstein cows (n=1035) Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743. 23438684 Milk 0 - 28.700 uM Gil A, Sanchez-Medina F: Acid-soluble nucleotides of cow's, goat's and sheep's milks, at different stages of lactation. J Dairy Res. 1981 Feb;48(1):35-44. 7196410 Placenta Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Testis 56 +/- 11 nmol/g of tissue By NMR Aidin Foroutan, Carolyn Fitzsimmons, Rupasri Mandal, Hamed Piri‐Moghadam, Jiamin Zheng, AnChi Guo, Carin Li, Le Luo Guan and David S. Wishart. The Bovine Metabolome. Metabolites 2020, 10, 233; doi:10.3390/metabo10060233 C00105 DB03685 FDB031248 5808 6030 16695 C00007311 UMP Uridine_monophosphate 33873 Wang Xing; Wang Xiuwen; Yin Mengxin; Xiao Zijun; Ma Cuiqing; Lin Zhixin; Wang Peng George; Xu Ping Production of uridine 5'-monophosphate by Corynebacterium ammoniagenes ATCC 6872 using a statistically improved biocatalytic process. Applied microbiology and biotechnology (2007), 76(2), 321-8. Gil A, Sanchez-Medina F: Acid-soluble nucleotides of cow's, goat's and sheep's milks, at different stages of lactation. J Dairy Res. 1981 Feb;48(1):35-44. 7196410 Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743. 23438684 BMDBP00149 Cytosolic purine 5'-nucleotidase O46411 NT5C2 Enzyme BMDBP00508 Inosine triphosphate pyrophosphatase Q2KIC5 ITPA Enzyme BMDBP00583 Uridine-cytidine kinase 1 Q0P5A4 UCK1 Enzyme BMDBP01219 UMP-CMP kinase Q2KIW9 CMPK1 Enzyme BMDBP02918 Calcium activated nucleotidase 1 E1BGL5 CANT1 Enzyme BMDBP02973 Cytidine/uridine monophosphate kinase 2 F1N2W6 CMPK2 Enzyme