1.0 2010-04-08 22:09:59 UTC 2019-11-26 03:06:09 UTC FDB012085 Orotidine Isolated from Phaseolus vulgaris (kidney bean) Orotidine is a nucleoside formed by attaching orotic acid to a ribose ring via a &#946;-N1-glycosidic bond. It is found in bacteria, fungi and plants. In humans, orotidine occurs as its 5'-phosphate (orotidylic acid), which is an intermediate in pyrimidine nucleotide biosynthesis (cytidine and uridine) that are found in nucleic acids. Ornitidine itself is not a component of nucleic acid. Large amounts of ornitidine are excreted in the urine of cancer patients treated with 6-azauridine. ; Orotidine is a nucleoside formed by attaching orotic acid to a ribose ring via a ?-N1-glycosidic bond. It is found in bacteria, fungi and plants. It was first isolated in 1951 from the fungus Neurospora by A. Michael Michelson, William Drell, and Herschel K. Mitchell. In humans, orotidine occurs as its 5'-phosphate (orotidylic acid), which is an intermediate in pyrimidine nucleotide biosynthesis (cytidine and uridine) that are found in nucleic acids. Orotidine itself is not a component of nucleic acid. Large amounts of orotidine are excreted in the urine of cancer patients treated with 6-azauridine. 1,2,3,6-Tetrahydro-2,6-dioxo-3-b-D-ribofuranosyl-4-pyrimidinecarboxylic acid, 9CI 3-b-D-Ribofuranosylorotic acid, 8CI 3-Ribofuranosylorotate 3-Ribofuranosylorotic acid 6-Carboxyuridine 6-Carboxyuridine, 8CI Orotic acid riboside C10H12N2O8 288.2109 288.05936537 3-[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-hydroxy-2-oxo-2,3-dihydropyrimidine-4-carboxylic acid 3-[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-hydroxy-2-oxopyrimidine-4-carboxylic acid 314-50-1 OCC1OC(C(O)C1O)N1C(=O)N=C(O)C=C1C(O)=O InChI=1S/C10H12N2O8/c13-2-4-6(15)7(16)8(20-4)12-3(9(17)18)1-5(14)11-10(12)19/h1,4,6-8,13,15-16H,2H2,(H,17,18)(H,11,14,19) FKCRAVPPBFWEJD-UHFFFAOYSA-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. Pyrimidine nucleosides Organic compounds Nucleosides, nucleotides, and analogues Pyrimidine nucleosides Aromatic heteromonocyclic compounds Azacyclic compounds Carboxylic acids Glycosylamines Heteroaromatic compounds Hydrocarbon derivatives Hydropyrimidine carboxylic acids and derivatives Lactams Monocarboxylic acids and derivatives Organic oxides Organonitrogen compounds Organopnictogen compounds Oxacyclic compounds Pentoses Primary alcohols Pyrimidinecarboxylic acids Pyrimidones Secondary alcohols Tetrahydrofurans Ureas Vinylogous amides Alcohol Aromatic heteromonocyclic compound Azacycle Carboxylic acid Carboxylic acid derivative Glycosyl compound Heteroaromatic compound Hydrocarbon derivative Hydropyrimidine Hydropyrimidine carboxylic acid derivative Lactam Monocarboxylic acid or derivatives 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 Pyrimidine-6-carboxylic acid Pyrimidine-6-carboxylic acid or derivatives Pyrimidone Secondary alcohol Tetrahydrofuran Urea Vinylogous amide Solid logp -2.23 ALOGPS logs -0.93 ALOGPS solubility 3.35e+01 g/l ALOGPS melting_point Mp 200° (turns brown near) logp -2.4 ChemAxon pka_strongest_acidic 3.43 ChemAxon pka_strongest_basic -3 ChemAxon iupac 3-[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-hydroxy-2-oxo-2,3-dihydropyrimidine-4-carboxylic acid ChemAxon average_mass 288.2109 ChemAxon mono_mass 288.05936537 ChemAxon smiles OCC1OC(C(O)C1O)N1C(=O)N=C(O)C=C1C(O)=O ChemAxon formula C10H12N2O8 ChemAxon inchi InChI=1S/C10H12N2O8/c13-2-4-6(15)7(16)8(20-4)12-3(9(17)18)1-5(14)11-10(12)19/h1,4,6-8,13,15-16H,2H2,(H,17,18)(H,11,14,19) ChemAxon inchikey FKCRAVPPBFWEJD-UHFFFAOYSA-N ChemAxon polar_surface_area 160.12 ChemAxon refractivity 60.19 ChemAxon polarizability 24.89 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 9 ChemAxon donor_count 5 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 95891 Specdb::MsMs 1078190 Specdb::MsMs 1078191 Specdb::MsMs 1078192 Specdb::MsMs 1200698 Specdb::MsMs 1200699 Specdb::MsMs 1200700 HMDB00788 #<Reference:0x000055ce32141f80> #<Reference:0x000055ce32141dc8> #<Reference:0x000055ce32141c10> Anatidae Type 1 specific Anatidae 8830 Beefalo Type 1 specific Bos taurus X Bison bison 297284 Bison Type 1 specific Bison bison 9901 Buffalo Type 1 specific Bubalus bubalis 89462 Cattle (Beef, Veal) Type 1 specific Bos taurus 9913 Chicken Type 1 specific Gallus gallus 9031 Columbidae (Dove, Pigeon) Type 1 specific Columbidae 8930 Deer Type 1 specific Cervidae 9850 Domestic goat Type 1 specific Capra aegagrus hircus 9925 Domestic pig Type 1 specific Sus scrofa domestica 9825 Elk Type 1 specific Cervus canadensis 1574408 Emu Type 1 specific Dromaius novaehollandiae 8790 European rabbit Type 1 specific Oryctolagus 9984 Green bean Type 1 specific Phaseolus vulgaris 3885 Greylag goose Type 1 specific Anser anser 8843 Guinea hen Type 1 specific Numida meleagris 8996 Horse Type 1 specific Equus caballus 9796 Mallard duck Type 1 specific Anas platyrhynchos 8839 Mountain hare Type 1 specific Lepus timidus 62621 Mule deer Type 1 specific Odocoileus 9871 Ostrich Type 1 specific Struthio camelus 8801 Pheasant Type 1 specific Phasianus colchicus 9054 Pulses Unknown generic Quail Type 1 specific Phasianidae 9005 Rabbit Type 1 specific Leporidae 9979 Rock ptarmigan Type 1 specific Lagopus muta 64668 Sheep (Mutton, Lamb) Type 1 specific Ovis aries 9940 Squab Type 1 specific Columba 8931 Turkey Type 1 specific Meleagris gallopavo 9103 Velvet duck Type 1 specific Melanitta fusca 371864 Wild boar Type 1 specific Sus scrofa 9823 Yellow wax bean Type 1 specific Phaseolus vulgaris 3885