File:Cytosine_structure_2022.svg · Wikimedia Commons · See Wikimedia Commons
cytosine
Sign in to saveAlso 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
Research
49,243 papers- High-precision cytosine base editors by evolving nucleic-acid-recognition hotspots in deaminase.Nature biotechnology · 2026Wu Y, Xiao YL, Tang WDOI: 10.1038/s41587-025-02678-w
- Cytosine Methylation Studies in Patients with Diabetic Kidney Disease.ReviewCurrent diabetes reports · 2019Aranyi T, Susztak KDOI: 10.1007/s11892-019-1214-6
- Cytosine base editors with increased PAM and deaminase motif flexibility for gene editing in zebrafish.Nature communications · 2024Zhang Y, Liu Y, Qin W et al.DOI: 10.1038/s41467-024-53735-y
- Cytosine methylation and DNA repair.ReviewCurrent topics in microbiology and immunology · 2006Walsh CP, Xu GLDOI: 10.1007/3-540-31390-7_11
- Hydroxymethyl cytosine marks in the human mitochondrial genome are dynamic in nature.Mitochondrion · 2016Ghosh S, Sengupta S, Scaria VDOI: 10.1016/j.mito.2016.01.003
- A new method for sequencing DNA.Proceedings of the National Academy of Sciences of the United States of America · 1977Maxam AM, Gilbert WDOI: 10.1073/pnas.74.2.560
- Phage arabinosyl-hydroxy-cytosine DNA modifications result in distinct evasion and sensitivity responses to phage defense systems.Cell host & microbe · 2025Mahler M, Cui L, Smith LM et al.DOI: 10.1016/j.chom.2025.06.005
- Antigen Retrieval for Immunostaining of Modified Cytosine Species.Methods in molecular biology (Clifton, N.J.) · 2021Celik-Uzuner SDOI: 10.1007/978-1-0716-0876-0_18
via PubMed
~3 min read
Encyclopedic overview
7 sectionsContents
- 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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