Orotidine

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Orotidine
Chemical structure of orotidine
Ball-and-stick model of 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
Identifiers
CAS number [314-50-1]
SMILES C1=C(N(C(=O)NC1=O)C2C(C(C(O2)CO)O)O)C(=O)O
Properties
Molecular formula C10H12N2O8
Molar mass 288.213 g/mol
Density x.xxx g/cm3
Melting point

200°C
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)
Infobox disclaimer and 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.

[edit] Note

  1. ^ A. Michael Michelson, William Drell, Herschel K. Mitchell (1951). "A new ribose nucleoside from Neurospora: "orotidine"". Proc Natl Acad Sci U S A 37 (7): 396–9. doi:10.1073/pnas.37.7.396. PMID 14853953.  Full text at PMC: 1063384 Free full text at PNAS