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
Canonical 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
The molarity calculator equation

Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)

The dilution calculator equation

Concentration (start) × Volume (start) = Concentration (final) × Volume (final)

This equation is commonly abbreviated as: C1V1 = C2V2

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