N(4)-methylcytidine Chemical Properties

Melting point:

202-203 °C(Solv: ethanol (64-17-5))

Boiling point:

504.2±60.0 °C(Predicted)

Density 

1.69±0.1 g/cm3(Predicted)

storage temp. 

2-8°C(protect from light)

solubility 

Aqueous Acid (Slightly), DMSO (Slightly), Methanol (Slightly), Water (Slightly)

pka

13.48±0.70(Predicted)

form 

Solid

color 

Off-White to Beige

Stability:

Hygroscopic

InChI

InChI=1S/C10H15N3O5/c1-11-6-2-3-13(10(17)12-6)9-8(16)7(15)5(4-14)18-9/h2-3,5,7-9,14-16H,4H2,1H3,(H,11,12,17)/t5-,7-,8-,9-/m1/s1

InChIKey

LZCNWAXLJWBRJE-ZOQUXTDFSA-N

SMILES

OC[C@H]1O[C@@H](N2C=CC(NC)=NC2=O)[C@H](O)[C@@H]1O

N(4)-methylcytidine Usage And Synthesis

Description

N4-Methylcytidine is a nucleoside analogue that inhibits synthesis of human mitochondrial DNA by inhibiting bacterial enzyme uridine-cytidine kinase, which converts uridine to cytidine in the mitochondria. N4-Methylcytidine has been shown to be potent against viruses such as HIV and herpes simplex virus type 1 (HSV-1) in cell culture studies. This antiviral effect is due to the interference with viral dna replication and protein synthesis by preventing incorporation of uracil into dna and ribosomal RNA.

Uses

N4-Methylcytidine (Nsc518744) is a cytidine nucleoside analog. Cytidine analogs have a mechanism of inhibiting DNA methyltransferases (such as Zebularine, HY-13420), and have potential anti-metabolic and anti-tumor activities[1].

Definition

ChEBI: N4-Methylcytidine is a pyrimidine nucleoside.

References

[1] Gowher H, et al. Mechanism of inhibition of DNA methyltransferases by cytidine analogs in cancer therapy. Cancer Biol Ther. 2004 Nov;3(11):1062-8. DOI:10.4161/cbt.3.11.1308