:Orotidine

{{chembox

| Watchedfields = changed

| verifiedrevid = 425975301

| Name = Orotidine

| ImageFile = Orotidine.svg

| ImageName = Chemical structure of orotidine

| ImageFile1 = Orotidine 3D.png

| ImageName1 = Ball-and-stick model of orotidine

| IUPACName = 2,6-Dioxo-3-(β-D-ribofuranosyl)-1,2,3,6-tetrahydropyrimidine-4-carboxylic acid

| SystematicName = 3-[(2R,3R,4S,5R)-3,4-Dihydroxy-6-(hydroxymethyl)oxolan-2-yl]-2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylic acid

| OtherNames = 3-Ribofuranosylorotic acid, 6-Carboxyuridine, orotate riboside

|Section1={{Chembox Identifiers

| CASNo_Ref = {{cascite|correct|??}}

| CASNo = 314-50-1

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = B350MC02GZ

| PubChem = 92751

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 83729

| SMILES = O=C(O)C=1N(C(=O)NC(=O)C=1)[C@@H]2O[C@@H]([C@@H](O)[C@H]2O)CO

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI =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)/t4-,6-,7-,8-/m1/s1

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = FKCRAVPPBFWEJD-XVFCMESISA-N

}}

|Section2={{Chembox Properties

| Formula = C₁₀H₁₂N₂O₈

| MolarMass = 288.213 g/mol

| Density =

| MeltingPtC = 200

| BoilingPt =

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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. It was first isolated in 1951 from the fungus Neurospora by A. Michael Michelson, William Drell, and Herschel K. Mitchell.{{cite journal |author1=A. Michael Michelson |author2=William Drell |author3=Herschel K. Mitchell |title=A new ribose nucleoside from Neurospora: "orotidine" |journal=Proc Natl Acad Sci USA |volume=37 |issue=7 |pages= 396–399 |year=1951 |pmid=14853953 |doi=10.1073/pnas.37.7.396 |pmc=1063384|bibcode=1951PNAS...37..396M |doi-access=free }} 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.

The symbol commonly used for orotidine is O or Ord.