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cytosine

File:Cytosine_structure_2022.svg · Wikimedia Commons · See Wikimedia Commons

EntityQ178425· pop 72· linked from 780 articles

Also known as Cyt, Zytosin, Cytosin, 4-amino-2-hydroxypyrimidine, 4-amino-2(1H)-pyrimidinone, 4-amino-3H-pyrimidin-2-one, 4-Amino-2-oxo-1,2-dihydropyrimidine, 6-amino-1,2-dihydropyrimidin-2-one

Cytosine (symbol C or Cyt) is one of the four nucleotide bases found in DNA and RNA, along with adenine, guanine, and thymine (uracil in RNA). It is a pyrimidine derivative, with a heterocyclic aromatic ring and two substituents attached (an amine group at position 4 and a keto group at position 2). The nucleoside of cytosine is cytidine. In Watson–Crick base pairing, it forms three hydrogen bonds with guanine.

OverviewAI-generated

Cytosine is a chemical compound with the formula C₄H₅N₃O. Its IUPAC name is 6-amino-1H-pyrimidin-2-one. The substance has a mass of 111.043 and a density of 1.6. It carries a charge of 0 and has two hydrogen bond donors and two hydrogen bond acceptors.

The compound is referenced by 780 other encyclopedia articles. In scientific literature, it appears in 49,243 PubMed entries. Its canonical SMILES structure is C1=C(NC(=O)N=C1)N. The XLogP value is -1.7, and the topological polar surface area is 67.5.

Synthesized by Vinony from 19 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
C4H5N3O
Molecular weight
111.1 g/mol
IUPAC name
6-amino-1H-pyrimidin-2-one
SMILES
C1=C(NC(=O)N=C1)N
InChIKey
OPTASPLRGRRNAP-UHFFFAOYSA-N
XLogP
-1.7
Polar surface area
67.5 Ų
H-bond donors
2
H-bond acceptors
2
Formal charge
0

via PubChem

~3 min read

Encyclopedic overview

7 sections
Contents
  • History
  • Chemical reactions
  • Biological function
  • Theoretical aspects
  • Notes
  • References
  • External links and citations

Cytosine (symbol C or Cyt) is one of the four nucleotide bases found in DNA and RNA, along with adenine, guanine, and thymine (uracil in RNA). It is a pyrimidine derivative, with a heterocyclic aromatic ring and two substituents attached (an amine group at position 4 and a keto group at position 2). The nucleoside of cytosine is cytidine. In Watson–Crick base pairing, it forms three hydrogen bonds with guanine.

==History== Cytosine was discovered and named by Albrecht Kossel and Albert Neumann in 1894 when it was hydrolyzed from calf thymus tissues. A structure was proposed in 1903, and was synthesized (and thus confirmed) in the laboratory in the same year.

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

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