Structure via PubChem · Public domain (PubChem)
orotidine
Sign in to saveAlso known as 1,2,3,6-tetrahydro2,6-dioxo-3beta-D-ribofuranosyl-4-pyrimidinecarboxylic acid, 6-carboxyuridine, 3-Ribofuranosylorotic acid, 3-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylic acid, Orotic acid riboside
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. 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-azaur
Chemical data
- Formula
- C10H12N2O8
- Molecular weight
- 288.21 g/mol
- IUPAC name
- 3-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-2,6-dioxopyrimidine-4-carboxylic acid
- SMILES
- C1=C(N(C(=O)NC1=O)[C@H]2[C@@H]([C@@H]([C@H](O2)CO)O)O)C(=O)O
- InChIKey
- FKCRAVPPBFWEJD-XVFCMESISA-N
- XLogP
- -2.6
- Polar surface area
- 157 Ų
- H-bond donors
- 5
- H-bond acceptors
- 8
- Formal charge
- 0
via PubChem
Wikidata facts
- Mass
- 288.059365
Show 5 more facts
- found in taxon
- Neurospora
- chemical formula
- C₁₀H₁₂N₂O₈
- Commons category
- Orotidine
- canonical SMILES
- C1=C(N(C(=O)NC1=O)C2C(C(C(O2)CO)O)O)C(=O)O
- isomeric SMILES
- C1=C(N(C(=O)NC1=O)[C@H]2[C@@H]([C@@H]([C@H](O2)CO)O)O)C(=O)O
Sources (2)
via Wikidata · CC0
~1 min read
Encyclopedic overview
1 sectionsContents
- Notes
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. 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.
Excerpted from Wikipedia’s “orotidine” article, available under the CC BY-SA 4.0 licence.