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
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
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
>300 °C(lit.)
Flash Point
223.4°C
Purity
98%
Density
0.48 g/cm3
Solubility
soluble in DMSO, Water
Appearance
White Solid
Storage
Keep container tightly closed in a dry and well-ventilated place.
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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