Orotidine

Orotidine
Chemical structure of orotidine
Chemical structure of orotidine
Ball-and-stick model of orotidine
Ball-and-stick model of orotidine
Names
IUPAC name
2,6-Dioxo-3-(β-D-ribofuranosyl)-1,2,3,6-tetrahydropyrimidine-4-carboxylic acid
Systematic IUPAC name
3-[(2R,3R,4S,5R)-3,4-Dihydroxy-6-(hydroxymethyl)oxolan-2-yl]-2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylic acid
Other names
3-Ribofuranosylorotic acid, 6-Carboxyuridine, orotate riboside
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • 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 checkY
    Key: FKCRAVPPBFWEJD-XVFCMESISA-N checkY
  • O=C(O)C=1N(C(=O)NC(=O)C=1)[C@@H]2O[C@@H]([C@@H](O)[C@H]2O)CO
Properties
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).
checkY verify (what is checkY☒N ?)

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.

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. Bibcode:1951PNAS...37..396M. doi:10.1073/pnas.37.7.396. PMC 1063384. PMID 14853953.

Content Disclaimer

Informasi ini disarikan dari Wikipedia dan disajikan kembali untuk tujuan edukasi. Konten tersedia di bawah lisensi CC BY-SA 3.0. Kami tidak bertanggung jawab atas ketidakakuratan data yang bersumber dari kontribusi publik tersebut.

  1. The information displayed on this website is sourced in part or in whole from Wikipedia and has been adapted for the purpose of restating it. We strive to provide accurate and relevant information, however:
  2. There is no guarantee of absolute accuracy. Wikipedia is an open, collaborative project that can be edited by anyone, so information is subject to change.
  3. It is not intended to constitute professional advice. The content displayed is for informational and educational purposes only. For important decisions (e.g., medical, legal, or financial), please consult a professional.
  4. Content copyright. Wikipedia is licensed under the Creative Commons Attribution-ShareAlike License (CC BY-SA). This means that content may be reused with appropriate attribution and shared under a similar license.
  5. Responsible use. Any risk arising from the use of information from this website is entirely the responsibility of the user.