Orotidine

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.[1] 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.

Orotidine

Names
IUPAC name 4-Pyrimidinecarboxylic acid, 1,2,3,6-tetrahydro-2,6-dioxo-3-beta-D-ribofuranosyl-
Other names 3-Ribofuranosylorotic acid, 6-Carboxyuridine, orotate riboside
Identifiers
CAS Number	314-50-1
3D model (JSmol)	Interactive image
ChemSpider	83729
PubChem CID	92751
UNII	B350MC02GZ
CompTox Dashboard (EPA)	DTXSID90953435
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)/t4-,6-,7-,8-/m1/s1 Key: FKCRAVPPBFWEJD-XVFCMESISA-N
SMILES O=C(O)C=1N(C(=O)NC(=O)C=1)[C@@H]2O[C@@H]([C@@H](O)[C@H]2O)CO
Properties
Chemical formula	C10H12N2O8
Molar mass	288.213 g/mol
Melting point	200 °C (392 °F; 473 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

The symbol commonly used for orotidine is O or Ord.

Notes

1. A. Michael Michelson; William Drell; Herschel K. Mitchell (1951). "A new ribose nucleoside from Neurospora: "orotidine"". Proc Natl Acad Sci USA. 37 (7): 396–399. doi:10.1073/pnas.37.7.396. PMC 1063384. PMID 14853953.