Cytosine
Product Information
Molecular Formula
C4H5N3O
Molecular Weight
111.10
Description
Cytosine is one of the four main 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 (anamine 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.
Synonyms
Cytarabine Impurity C; 4-Aminopyrimidin-2(1H)-one; 6-Amino-2(1H)-pyrimidinone; 4-Amino-1H-pyrimidin-2-one; 4-Amino-2(1H)-pyrimidinone; 4-Amino-2-hydroxypyrimidine; 4-Aminouracil; Gemcitabine EP Impurity A; Lamivudine EP Impurity E; 2-Hydroxy-4-pyrimidinamine; 4-Amino-2-oxo-1,2-dihydropyrimidine; Cytosines; Cytosinimine; NSC 27787; Cytarabine EP Impurity C; Gemcitabine hydrochloride EP Impurity A
IUPAC Name
6-amino-1H-pyrimidin-2-one
SMILES
C1=C(NC(=O)N=C1)N
InChI
InChI=1S/C4H5N3O/c5-3-1-2-6-4(8)7-3/h1-2H,(H3,5,6,7,8)
InChI Key
OPTASPLRGRRNAP-UHFFFAOYSA-N
Boiling Point
445.8°C at 760 mmHg
Melting Point
322.5 °C (dec.)
Flash Point
223.4°C
Purity
98%
Density
1.562 g/cm3
Solubility
Soluble in DMSO, Water
Appearance
White Solid
Storage
Tightly closed. Dry.
Refractive Index
1.5000 (estimate)
Stability
Stable. Incompatible with strong oxidizing agents.
LogP
-0.06670
Vapor Pressure
0.00109 [mmHg]
Safety Information
Hazards
H315 - H319 - H335
Precautionary Statement
P305 + P351 + P338
Computed Properties
XLogP3
-1.7
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
2
Rotatable Bond Count
0
Exact Mass
111.043261792 g/mol
Monoisotopic Mass
111.043261792 g/mol
Topological Polar Surface Area
67.5Ų
Heavy Atom Count
8
Formal Charge
0
Complexity
170
Isotope Atom Count
0
Defined Atom Stereocenter Count
0
Undefined Atom Stereocenter Count
0
Defined Bond Stereocenter Count
0
Undefined Bond Stereocenter Count
0
Covalently-Bonded Unit Count
1
Compound Is Canonicalized
Yes
Patents
| Publication Number | Title | Priority Date |
|---|---|---|
| US-2016002204-A1 | Gls1 inhibitors for treating disease | 2014-07-03 |
| WO-2015172889-A1 | Peptide nucleic acid monomers and oligomers | 2014-05-16 |
| WO-2015161137-A1 | 3'-substituted methyl or alkynyl nucleosides for the treatment of hcv | 2014-04-16 |
| WO-2015157535-A2 | Synthetic peptides, enzymatic formation of pericellular hydrogels/nanofibrils, and methods of use | 2014-04-09 |
| WO-2015157555-A2 | Import of unnatural or modified nucleoside triphosphates into cells via nucleic acid triphosphate transporters | 2014-04-09 |
| WO-2015095305-A1 | Production of cyclic phosphate, phosphoramidate, thiophosphate, and phosphonate nucleoside compounds | 2013-12-17 |
| WO-2015048575-A1 | Low dielectric constant, low dielectric dissipation factor coatings, films and adhesives | 2013-09-26 |
| WO-2015023776-A2 | Deoxycytidine kinase inhibitors | 2013-08-13 |
| US-2016075693-A1 | Avanafil preparation method | 2013-05-23 |
| US-2014275537-A1 | Process for the preparation of 4-amino-1-((1s,4r,5s)-2-fluoro-4,5-dihydroxy-3-hydroxymethyl-cyclopent-2-enyl)-1h-pyrimidin-2-one | 2013-03-15 |
Literatures
| PMID | Publication Date | Title | Journal |
|---|---|---|---|
| 33834883 | 2021-12-01 | Initial Experience Treating HPV-Related Laryngeal Diseases with Oral Brincidofovir: A Pilot Study | The Annals of otology, rhinology, and laryngology |
| 33536322 | 2021-02-03 | Pharmacokinetics and Efficacy of a Potential Smallpox Therapeutic, Brincidofovir, in a Lethal Monkeypox Virus Animal Model | mSphere |
| 31555880 | 2019-11-01 | Gene expression and cytosine DNA methylation alterations in induced pluripotent stem-cell-derived human hepatocytes treated with low doses of chemical carcinogens | Archives of toxicology |
| 31385694 | 2019-09-03 | Complex Interplay Among Nuclear Receptor Ligands, Cytosine Methylation, and the Metabolome in Driving Tris(1,3-dichloro-2-propyl)phosphate-Induced Epiboly Defects in Zebrafish | Environmental science & technology |
| 27387713 | 2017-03-01 | Furan-induced transcriptomic and gene-specific DNA methylation changes in the livers of Fischer 344 rats in a 2-year carcinogenicity study | Archives of toxicology |
| 28215138 | 2017-01-01 | Amino Acid Ester Prodrugs of Nucleoside and Nucleotide Antivirals | Mini reviews in medicinal chemistry |
| 26732893 | 2016-01-18 | Evaluation of 5-methylcytosine and 5-hydroxymethylcytosine as potential biomarkers for characterisation of chemical allergens | Toxicology |
| 25690533 | 2015-12-01 | The effect of a methyl-deficient diet on the global DNA methylation and the DNA methylation regulatory pathways | Journal of applied toxicology : JAT |
| 26436839 | 2015-11-01 | New IDH1 mutant inhibitors for treatment of acute myeloid leukemia | Nature chemical biology |
| 25448811 | 2015-02-01 | Intracellular concentrations determine the cytotoxicity of adefovir, cidofovir and tenofovir | Toxicology in vitro : an international journal published in association with BIBRA |
