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uridine

Structure via PubChem · Public domain (PubChem)

EntityQ422573· pop 39· linked from 510 articles

Also known as 1-beta-D-ribofuranosylpyrimidine-2,4(1H,3H)-dione, Uridin, Urd, 1-beta-D-ribofuranosyluracil, u, beta-Uridine, 1-[(2R,3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidine-2,4-dione, 1-[(2R,3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione

Uridine (symbol U or Urd) is a glycosylated pyrimidine analog containing uracil attached to a ribose ring (or more specifically, a ribofuranose) via a β-N1-glycosidic bond. The analog is one of the five standard nucleosides which make up nucleic acids, the others being adenosine, thymidine, cytidine and guanosine. The five nucleosides are commonly abbreviated to their symbols, U, A, dT, C, and G, respectively. However, thymidine is more commonly written as 'dT' ('d' represents 'deoxy') as it contains a 2'-deoxyribofuranose moiety rather than the ribofuranose ring found in uridine. This is beca

OverviewAI-generated

Uridine is a chemical compound with the formula C₉H₁₂N₂O₆. Its IUPAC name is 1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione. The substance has a mass of 244.07 and a melting point of 168.

Chemical properties include a charge of 0, an xlogp of -2, and a topological polar surface area of 119. The molecule contains four hydrogen bond donors and six hydrogen bond acceptors. Uridine is referenced by 510 other encyclopedia articles.

Synthesized by Vinony from 19 facts across 4 sources: Wikidata, PubMed, PubChem, Vinony graph. Generated from structured data (not the Wikipedia text) and checked against those facts — may still contain errors.

Chemical data

Formula
C9H12N2O6
Molecular weight
244.2 g/mol
IUPAC name
1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
SMILES
C1=CN(C(=O)NC1=O)[C@H]2[C@@H]([C@@H]([C@H](O2)CO)O)O
InChIKey
DRTQHJPVMGBUCF-XVFCMESISA-N
XLogP
-2
Polar surface area
119 Ų
H-bond donors
4
H-bond acceptors
6
Formal charge
0

via PubChem

Research

57,460 papers

via PubMed

~4 min read

Encyclopedic overview

5 sections
Contents
  • Biosynthesis
  • Dietary sources
  • Galactose glycolysis
  • See also
  • References

Uridine (symbol U or Urd) is a glycosylated pyrimidine analog containing uracil attached to a ribose ring (or more specifically, a ribofuranose) via a β-N1-glycosidic bond. The analog is one of the five standard nucleosides which make up nucleic acids, the others being adenosine, thymidine, cytidine and guanosine. The five nucleosides are commonly abbreviated to their symbols, U, A, dT, C, and G, respectively. However, thymidine is more commonly written as 'dT' ('d' represents 'deoxy') as it contains a 2'-deoxyribofuranose moiety rather than the ribofuranose ring found in uridine. This is because thymidine is found in deoxyribonucleic acid (DNA) and usually not in ribonucleic acid (RNA). Conversely, uridine is found in RNA and not DNA. The remaining three nucleosides may be found in both RNA and DNA. In RNA, they would be represented as A, C and G whereas in DNA they would be represented as dA, dC and dG.

== Biosynthesis == Uridine is widely produced in nature as uridine monophosphate (uridylate) by de novo synthesis by the decarboxylation of orotidylate, which is catalyzed by orotidylate decarboxylase. The orotidylate is produced from orotate, which is combined with 5-phosphoribosyl-1-pyrophosphate (PRPP) to form orotidylate by pyrimidine phosphoribosyltransferase. PRPP is created from ribose-5-phosphate by a further phosphorylation, serving as an energetic molecule to drive the reaction forward, while orotate is generated in several steps from carbamoyl phosphate and aspartate.

Excerpted from Wikipedia’s “uridine” article, available under the CC BY-SA 4.0 licence.