1.02010-04-08 22:09:59 UTC2019-11-26 03:06:09 UTCFDB012085OrotidineIsolated from Phaseolus vulgaris (kidney bean)
Orotidine is a nucleoside formed by attaching orotic acid to a ribose ring via a β-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, 9CI3-b-D-Ribofuranosylorotic acid, 8CI3-Ribofuranosylorotate3-Ribofuranosylorotic acid6-Carboxyuridine6-Carboxyuridine, 8CIOrotic acid ribosideC10H12N2O8288.2109288.059365373-[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-hydroxy-2-oxo-2,3-dihydropyrimidine-4-carboxylic acid3-[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-hydroxy-2-oxopyrimidine-4-carboxylic acid314-50-1OCC1OC(C(O)C1O)N1C(=O)N=C(O)C=C1C(O)=OInChI=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 nucleosidesOrganic compoundsNucleosides, nucleotides, and analoguesPyrimidine nucleosidesAromatic heteromonocyclic compoundsAzacyclic compoundsCarboxylic acidsGlycosylaminesHeteroaromatic compoundsHydrocarbon derivativesHydropyrimidine carboxylic acids and derivativesLactamsMonocarboxylic acids and derivativesOrganic oxidesOrganonitrogen compoundsOrganopnictogen compoundsOxacyclic compoundsPentosesPrimary alcoholsPyrimidinecarboxylic acidsPyrimidonesSecondary alcoholsTetrahydrofuransUreasVinylogous amidesAlcoholAromatic heteromonocyclic compoundAzacycleCarboxylic acidCarboxylic acid derivativeGlycosyl compoundHeteroaromatic compoundHydrocarbon derivativeHydropyrimidineHydropyrimidine carboxylic acid derivativeLactamMonocarboxylic acid or derivativesMonosaccharideN-glycosyl compoundOrganic nitrogen compoundOrganic oxideOrganic oxygen compoundOrganoheterocyclic compoundOrganonitrogen compoundOrganooxygen compoundOrganopnictogen compoundOxacyclePentose monosaccharidePrimary alcoholPyrimidinePyrimidine nucleosidePyrimidine-6-carboxylic acidPyrimidine-6-carboxylic acid or derivativesPyrimidoneSecondary alcoholTetrahydrofuranUreaVinylogous amideSolidlogp-2.23logs-0.93solubility3.35e+01 g/lmelting_pointMp 200° (turns brown near)logp-2.4pka_strongest_acidic3.43pka_strongest_basic-3iupac3-[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-hydroxy-2-oxo-2,3-dihydropyrimidine-4-carboxylic acidaverage_mass288.2109mono_mass288.05936537smilesOCC1OC(C(O)C1O)N1C(=O)N=C(O)C=C1C(O)=OformulaC10H12N2O8inchiInChI=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)inchikeyFKCRAVPPBFWEJD-UHFFFAOYSA-Npolar_surface_area160.12refractivity60.19polarizability24.89rotatable_bond_count3acceptor_count9donor_count5physiological_charge-1formal_charge0Specdb::CMs95891Specdb::MsMs1078190Specdb::MsMs1078191Specdb::MsMs1078192Specdb::MsMs1200698Specdb::MsMs1200699Specdb::MsMs1200700HMDB00788#<Reference:0x000055567509d078>#<Reference:0x000055567509ce98>#<Reference:0x000055567509cab0>AnatidaeType 1specificAnatidae8830BeefaloType 1specificBos taurus X Bison bison297284BisonType 1specificBison bison9901BuffaloType 1specificBubalus bubalis89462Cattle (Beef, Veal)Type 1specificBos taurus9913ChickenType 1specificGallus gallus9031Columbidae (Dove, Pigeon)Type 1specificColumbidae8930DeerType 1specificCervidae9850Domestic goatType 1specificCapra aegagrus hircus9925Domestic pigType 1specificSus scrofa domestica9825ElkType 1specificCervus canadensis1574408EmuType 1specificDromaius novaehollandiae8790European rabbitType 1specificOryctolagus9984Green beanType 1specificPhaseolus vulgaris3885Greylag gooseType 1specificAnser anser8843Guinea henType 1specificNumida meleagris8996HorseType 1specificEquus caballus9796Mallard duckType 1specificAnas platyrhynchos8839Mountain hareType 1specificLepus timidus62621Mule deerType 1specificOdocoileus9871OstrichType 1specificStruthio camelus8801PheasantType 1specificPhasianus colchicus9054PulsesUnknowngenericQuailType 1specificPhasianidae9005RabbitType 1specificLeporidae9979Rock ptarmiganType 1specificLagopus muta64668Sheep (Mutton, Lamb)Type 1specificOvis aries9940SquabType 1specificColumba8931TurkeyType 1specificMeleagris gallopavo9103Velvet duckType 1specificMelanitta fusca371864Wild boarType 1specificSus scrofa9823Yellow wax beanType 1specificPhaseolus vulgaris3885