Orotidine

Orotidine
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
PubChem 92751
ChemSpider 83729 Y
Jmol-3D images Image 1
Properties
Molecular formula C10H12N2O8
Molar mass 288.213 g/mol
Density x.xxx g/cm3
Melting point

200°C
 Y (verify) (what is: Y/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

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.

The symbol commonly used for orotidine is O or Ord.

Note

  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. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=1063384.  Full text at PMC: 1063384 Free full text at PNAS