1.0 2016-09-30 22:28:00 UTC 2020-06-04 20:49:44 UTC BMDB0000296 BMDB00296 Uridine Uridine, also known as beta-uridine or allo uridine, belongs to the class of organic compounds known as pyrimidine nucleosides. Pyrimidine nucleosides are compounds comprising a pyrimidine base attached to a ribosyl or deoxyribosyl moiety. Uridine exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. Uridine exists in all living species, ranging from bacteria to humans. In cattle, uridine is involved in the metabolic pathway called lactose synthesis pathway. Uridine has been found to be associated with several diseases known as degenerative disc disease, canavan disease, and ulcerative colitis; also uridine has been linked to several inborn metabolic disorders including argininemia and lesch-nyhan syndrome. 1-beta-D-Ribofuranosylpyrimidine-2,4(1H,3H)-dione 1-beta-D-Ribofuranosyluracil beta-Uridine u Urd Uridin 1-b-D-Ribofuranosylpyrimidine-2,4(1H,3H)-dione 1-Β-D-ribofuranosylpyrimidine-2,4(1H,3H)-dione 1-b-D-Ribofuranosyluracil 1-Β-D-ribofuranosyluracil b-Uridine Β-uridine 1-b-D-Ribofuranosyl-2,4(1H,3H)-pyrimidinedione 1-beta-delta-Ribofuranosyl-2,4(1H,3H)-pyrimidinedione 1-beta-delta-Ribofuranosyluracil b-D-Ribofuranoside 2,4(1H,3H)-pyrimidinedione-1 beta-delta-Ribofuranoside 2,4(1H,3H)-pyrimidinedione-1 Allo uridine Allo-uridine Allouridine C9H12N2O6 244.2014 244.069536126 1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,3,4-tetrahydropyrimidine-2,4-dione uridine 58-96-8 OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=CC(=O)NC1=O InChI=1S/C9H12N2O6/c12-3-4-6(14)7(15)8(17-4)11-2-1-5(13)10-9(11)16/h1-2,4,6-8,12,14-15H,3H2,(H,10,13,16)/t4-,6-,7-,8-/m1/s1 DRTQHJPVMGBUCF-XVFCMESISA-N belongs to the class of organic compounds known as pyrimidine nucleosides. Pyrimidine nucleosides are compounds comprising a pyrimidine base attached to a ribosyl or deoxyribosyl moiety. Organic compounds Nucleosides, nucleotides, and analogues Pyrimidine nucleosides Pyrimidine nucleosides Azacyclic compounds Glycosylamines Heteroaromatic compounds Hydrocarbon derivatives Hydropyrimidines Lactams Organic oxides Organonitrogen compounds Organopnictogen compounds Oxacyclic compounds Pentoses Primary alcohols Pyrimidones Secondary alcohols Tetrahydrofurans Ureas Vinylogous amides Alcohol Aromatic heteromonocyclic compound Azacycle Glycosyl compound Heteroaromatic compound Hydrocarbon derivative Hydropyrimidine Lactam Monosaccharide N-glycosyl compound Organic nitrogen compound Organic oxide Organic oxygen compound Organoheterocyclic compound Organonitrogen compound Organooxygen compound Organopnictogen compound Oxacycle Pentose monosaccharide Primary alcohol Pyrimidine Pyrimidine nucleoside Pyrimidone Secondary alcohol Tetrahydrofuran Urea Vinylogous amide Aromatic heteromonocyclic compounds Ribonucleosides uridines Solid melting_point 163 °C logp -1.98 HANSCH,C ET AL. (1995) logp -1.84 ALOGPS logs -0.26 ALOGPS logp -2.4 ChemAxon pka_strongest_acidic 9.7 ChemAxon pka_strongest_basic -3 ChemAxon iupac 1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,3,4-tetrahydropyrimidine-2,4-dione ChemAxon average_mass 244.2014 ChemAxon mono_mass 244.069536126 ChemAxon smiles OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=CC(=O)NC1=O ChemAxon formula C9H12N2O6 ChemAxon inchi InChI=1S/C9H12N2O6/c12-3-4-6(14)7(15)8(17-4)11-2-1-5(13)10-9(11)16/h1-2,4,6-8,12,14-15H,3H2,(H,10,13,16)/t4-,6-,7-,8-/m1/s1 ChemAxon inchikey DRTQHJPVMGBUCF-XVFCMESISA-N ChemAxon polar_surface_area 119.33 ChemAxon refractivity 52.57 ChemAxon polarizability 21.81 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 6 ChemAxon donor_count 4 ChemAxon physiological_charge 0 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 Pyrimidine Metabolism SMP0087247 Specdb::EiMs 1980 Specdb::NmrTwoD 1015 Specdb::NmrTwoD 1261 Specdb::MsMs 504 Specdb::MsMs 505 Specdb::MsMs 506 Specdb::MsMs 3933 Specdb::MsMs 3934 Specdb::MsMs 3935 Specdb::MsMs 3936 Specdb::MsMs 3937 Specdb::MsMs 3938 Specdb::MsMs 3939 Specdb::MsMs 3940 Specdb::MsMs 3941 Specdb::MsMs 3942 Specdb::MsMs 3943 Specdb::MsMs 3944 Specdb::MsMs 3945 Specdb::MsMs 3946 Specdb::MsMs 3947 Specdb::MsMs 3948 Specdb::MsMs 3949 Specdb::MsMs 3950 Specdb::MsMs 3951 Specdb::MsMs 3952 Specdb::MsMs 3953 Specdb::MsMs 3954 Specdb::NmrOneD 1228 Specdb::NmrOneD 1319 Specdb::NmrOneD 4774 Specdb::NmrOneD 6482 Specdb::NmrOneD 6483 Specdb::NmrOneD 6484 Specdb::NmrOneD 6485 Specdb::NmrOneD 6486 Specdb::NmrOneD 6487 Specdb::NmrOneD 6488 Specdb::NmrOneD 6489 Specdb::NmrOneD 6490 Specdb::NmrOneD 6491 Specdb::NmrOneD 6492 Specdb::NmrOneD 6493 Specdb::NmrOneD 6494 Specdb::NmrOneD 6495 Specdb::NmrOneD 6496 Specdb::NmrOneD 6497 Specdb::NmrOneD 6498 Specdb::NmrOneD 6499 Specdb::NmrOneD 6500 Specdb::NmrOneD 6501 Specdb::NmrOneD 166343 Specdb::NmrOneD 166506 Specdb::CMs 524 Specdb::CMs 525 Specdb::CMs 526 Specdb::CMs 527 Specdb::CMs 1976 Specdb::CMs 1985 Specdb::CMs 2456 Specdb::CMs 30409 Specdb::CMs 30709 Specdb::CMs 30710 Specdb::CMs 30764 Specdb::CMs 31118 Specdb::CMs 31119 Specdb::CMs 32283 Specdb::CMs 32284 Specdb::CMs 37409 Specdb::CMs 133686 Specdb::CMs 141420 Specdb::CMs 1057331 Specdb::CMs 1057333 Specdb::CMs 1057335 Specdb::CMs 1057337 Specdb::CMs 1057339 Specdb::CMs 1057341 Specdb::CMs 1057342 Blood 3 +/- 1 uM 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 Colostrum Detected by NMR Zanardi E, Caligiani A, Palla L, Mariani M, Ghidini S, Di Ciccio PA, Palla G, Ianieri A: Metabolic profiling by (1)H NMR of ground beef irradiated at different irradiation doses. Meat Sci. 2015 May;103:83-9. doi: 10.1016/j.meatsci.2015.01.005. Epub 2015 Jan 15. 25637742 Liver 344 +/- 86 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 8 multiparous Chinese Holstein dairy cows fed in the Hangzhou Hangjiang Dairy Farm based on the milk production under corn stover based diets. Detection used gas chromatography time-of-flight/mass spectrometry (GC-TOF/MS) platform. Sun HZ, Zhou M, Wang O, Chen Y, Liu JX, Guan LL: Multi-omics reveals functional genomic and metabolic mechanisms of milk production and quality in dairy cows. Bioinformatics. 2020 Apr 15;36(8):2530-2537. doi: 10.1093/bioinformatics/btz951. 31873721 Liver 8 multiparous Chinese Holstein dairy cows fed in the Hangzhou Hangjiang Dairy Farm based on the milk production under alfalfa hay based diets. Detection used gas chromatography time-of-flight/mass spectrometry (GC-TOF/MS) platform. Sun HZ, Zhou M, Wang O, Chen Y, Liu JX, Guan LL: Multi-omics reveals functional genomic and metabolic mechanisms of milk production and quality in dairy cows. Bioinformatics. 2020 Apr 15;36(8):2530-2537. doi: 10.1093/bioinformatics/btz951. 31873721 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 Mammary Gland 8 multiparous Chinese Holstein dairy cows fed in the Hangzhou Hangjiang Dairy Farm based on the milk production under corn stover based diets. Detection used gas chromatography time-of-flight/mass spectrometry (GC-TOF/MS) platform. Sun HZ, Zhou M, Wang O, Chen Y, Liu JX, Guan LL: Multi-omics reveals functional genomic and metabolic mechanisms of milk production and quality in dairy cows. Bioinformatics. 2020 Apr 15;36(8):2530-2537. doi: 10.1093/bioinformatics/btz951. 31873721 Mammary Gland 8 multiparous Chinese Holstein dairy cows fed in the Hangzhou Hangjiang Dairy Farm based on the milk production under alfalfa hay based diets. Detection used gas chromatography time-of-flight/mass spectrometry (GC-TOF/MS) platform. Sun HZ, Zhou M, Wang O, Chen Y, Liu JX, Guan LL: Multi-omics reveals functional genomic and metabolic mechanisms of milk production and quality in dairy cows. Bioinformatics. 2020 Apr 15;36(8):2530-2537. doi: 10.1093/bioinformatics/btz951. 31873721 Milk 16.07 +/- 4.91 uM Raw milk metabolite measured during mid-lactation from cows fed diets consisting of total mixed ration (TMR), by 1H-NMR O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027. 29642378 Milk 14.690 +/- 4.730 uM Raw milk Schlimme E, Raezke KP, Ott FG: Ribonucleosides as minor milk constituents. Z Ernahrungswiss. 1991 Jun;30(2):138-52. 1897275 Milk 31 +/- 3 uM 1% milk by NMR Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204. 30994344 Milk 27 +/- 2 uM 2% milk by NMR Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204. 30994344 Milk 28 +/- 2 uM 3.25% milk by NMR Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204. 30994344 Milk 30 +/- 3 uM Skim milk by NMR Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204. 30994344 Milk 73.1 uM Raw whole milk Tiemeyer W, Stohrer M, Giesecke D: Metabolites of nucleic acids in bovine milk. J Dairy Sci. 1984 Apr;67(4):723-8. doi: 10.3168/jds.S0022-0302(84)81361-2. 6539345 Milk 14.7 uM Raw milk Schlimme E, Martin D, Meisel H: Nucleosides and nucleotides: natural bioactive substances in milk and colostrum. Br J Nutr. 2000 Nov;84 Suppl 1:S59-68. 11242448 Milk Commercial, conventional whole milk Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff, John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375-386 doi: 10.1007/s11306-009-0160-8 Milk 11.76 +/- 1.81 uM Raw milk metabolite measured during mid-lactation from cows fed diets consisting of perennial ryegrass (GRS), by 1H-NMR O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027. 29642378 Milk 11.78 +/- 2.37 uM Raw milk metabolite measured during mid-lactation from cows fed diets consisting of perennial ryegrass and white clover (CLV), by 1H-NMR O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027. 29642378 Muscle Detected by NMR Zanardi E, Caligiani A, Palla L, Mariani M, Ghidini S, Di Ciccio PA, Palla G, Ianieri A: Metabolic profiling by (1)H NMR of ground beef irradiated at different irradiation doses. Meat Sci. 2015 May;103:83-9. doi: 10.1016/j.meatsci.2015.01.005. Epub 2015 Jan 15. 25637742 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 Ruminal Fluid 18 +/- 10 uM 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 Ruminal Fluid 2-17 uM By NMR O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027. 29642378 Testis 156 +/- 36 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 Urine Detected by NMR. Urine samples were from 32 Holstein cows that were fed crude protein. Bertram HC, Yde CC, Zhang X, Kristensen NB: Effect of dietary nitrogen content on the urine metabolite profile of dairy cows assessed by nuclear magnetic resonance (NMR)-based metabolomics. J Agric Food Chem. 2011 Dec 14;59(23):12499-505. doi: 10.1021/jf204201f. Epub 2011 Nov 17. 22059599 C00299 5807 DB02745 FDB007411 6029 16704 C00019674 URIDINE Uridine 34541 90 Doi, Muneharu; Asahi, Satoru; Izawa, Motoo. Fermentative production of uridine and cytidine. Baiosaiensu to Indasutori (1993), 51(12), 972-6. Schlimme E, Raezke KP, Ott FG: Ribonucleosides as minor milk constituents. Z Ernahrungswiss. 1991 Jun;30(2):138-52. 1897275 Tiemeyer W, Stohrer M, Giesecke D: Metabolites of nucleic acids in bovine milk. J Dairy Sci. 1984 Apr;67(4):723-8. doi: 10.3168/jds.S0022-0302(84)81361-2. 6539345 Schlimme E, Martin D, Meisel H: Nucleosides and nucleotides: natural bioactive substances in milk and colostrum. Br J Nutr. 2000 Nov;84 Suppl 1:S59-68. 11242448 Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28. 28306241 O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027. 29642378 Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14. 29291809 Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386 A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation) BMDBP00149 Cytosolic purine 5'-nucleotidase O46411 NT5C2 Enzyme BMDBP00579 tRNA pseudouridine synthase A6QP68 PUSL1 Enzyme BMDBP00580 Single-stranded DNA cytosine deaminase Q2PT36 AICDA Enzyme BMDBP00581 Pseudouridylate synthase 7 homolog Q08DI8 PUS7 Enzyme BMDBP00582 tRNA pseudouridine(38/39) synthase Q3SX07 PUS3 Enzyme BMDBP00583 Uridine-cytidine kinase 1 Q0P5A4 UCK1 Enzyme BMDBP02974 Uridine phosphorylase Q0VCM7 UPP2 Enzyme