uracil

Also known as Ura, Urazil, 2,4(1H,3H)-pyrimidinedione, 2,4-Pyrimidinedione, 2,4-Dioxopyrimidine, 2,4-Pyrimidinediol, Hybar X, 2,4-Dihydroxypyrimidine

Uracil () (symbol U or Ura) is one of the four nucleotide bases in the nucleic acid RNA. The others are adenine (A), cytosine (C), and guanine (G). In RNA, uracil binds to adenine via two hydrogen bonds. In DNA, the uracil nucleobase is replaced by thymine (T). Uracil is a demethylated form of thymine.

OverviewAI-generated

Uracil is a chemical compound with the formula C₄H₄N₂O₂. Its IUPAC name is 1H-pyrimidine-2,4-dione. The substance has a mass of 112.027 and a melting point of 339. It exhibits a pKa of 9.45 and a solubility of 4.62.

Chemical properties include a canonical SMILES string of C1=CNC(=O)NC1=O. The compound has a charge of 0, an xlogp of -1.1, and a tpsa of 58.2. It contains two hydrogen bond donors and two hydrogen bond acceptors. A separate weight value of 112.09 is also recorded.

Uracil is referenced by 551 other encyclopedia articles. A PubMed query for uracil returns a count of 93064.

Synthesized by Vinony from 20 facts across 4 sources: Wikidata, PubChem, PubMed, Vinony graph. Generated from structured data (not the Wikipedia text) and checked against those facts — may still contain errors.

Chemical data

Formula: C4H4N2O2
Molecular weight: 112.09 g/mol
IUPAC name: 1H-pyrimidine-2,4-dione
SMILES: C1=CNC(=O)NC1=O
InChIKey: ISAKRJDGNUQOIC-UHFFFAOYSA-N
XLogP: -1.1
Polar surface area: 58.2 Å²
H-bond donors: 2
H-bond acceptors: 2
Formal charge: 0

via PubChem

Research

93,064 papers

Detection of Genomic Uracil Patterns.ReviewInternational journal of molecular sciences · 2021Békési A, Holub E, Pálinkás HL et al.DOI: 10.3390/ijms22083902
Uracil in DNA--its biological significance.ReviewMutation research · 2010Olinski R, Jurgowiak M, Zaremba TDOI: 10.1016/j.mrrev.2010.08.001
Medicinal chemistry aspects of uracil containing dUTPase inhibitors targeting colorectal cancer.ReviewDrug discovery today · 2024Backer N, Kumar A, Singh AK et al.DOI: 10.1016/j.drudis.2023.103853
Genomic uracil and human disease.ReviewExperimental cell research · 2006Hagen L, Peña-Diaz J, Kavli B et al.DOI: 10.1016/j.yexcr.2006.06.015
Therapeutic potential of uracil and its derivatives in countering pathogenic and physiological disorders.ReviewEuropean journal of medicinal chemistry · 2020Ramesh D, Vijayakumar BG, Kannan TDOI: 10.1016/j.ejmech.2020.112801
Register-Shifted Structures in Base-Flipped Uracil-Damaged DNA.Journal of the American Chemical Society · 2023Orndorff PB, van der Vaart ADOI: 10.1021/jacs.3c05890
Uracil in DNA--general mutagen, but normal intermediate in acquired immunity.ReviewDNA repair · 2007Kavli B, Otterlei M, Slupphaug G et al.DOI: 10.1016/j.dnarep.2006.10.014
Precluding uracil from DNA.ReviewStructure (London, England : 1993) · 1996Vassylyev DG, Morikawa KDOI: 10.1016/s0969-2126(96)00145-1

via PubMed

~11 min read

Encyclopedic overview

10 sections

Contents

Properties
In DNA
Synthesis
Biological
Laboratory
Prebiotic
Reactions
Uses
References
External links

Uracil is a common and naturally occurring pyrimidine derivative. The name "uracil" was coined in 1885 by the German chemist Robert Behrend, who was attempting to synthesize derivatives of uric acid. Originally discovered in 1900 by Alberto Ascoli, it was isolated by hydrolysis of yeast nuclein; it was also found in bovine thymus and spleen, herring sperm, and wheat germ. It is a planar, unsaturated compound that has the ability to absorb light.

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