Isocytosine

Names

[ CAS No. ]:
108-53-2

[ Name ]:
Isocytosine

[Synonym ]:
4(1H)-Pyrimidinone, 2-amino- (9CI)
2-amino-4-oxo-3,4-dihydropyrimidine
4(3H)-pyrimidinone, 2-amino-
2-amino-3H-pyrimidin-4-one
Isocytosine
2-Amino-4-pyrimidone
2-Aminopyrimidin-4-ol
2-amino-4-hydroxypyrimine
2-Amino-4-hydroxypyrimidine
4-Hydroxy-2-aminopyrimidine
2-amino-1H-pyrimidin-6-one
MFCD00057557
2-Amino-4-hydroxypyrimidine,2-Aminouracil
2-Aminopyrimidin-4(1H)-one
Iso Cytosine
2-Amino-4(1H)-pyrimidinone
2-Aminopyrimidin-4(3H)-one
2-Amino-6-hydroxpyrimidine
EINECS 203-592-0
2-aminouracil
4-Pyrimidinol, 2-amino-

Biological Activity

[Description]:

Isocytosine is a non-natural nucleobase and an isomer of cytosine. It is used in combination with Isoguanine in studies of unnatural nucleic acid analogues of the normal base pairs in DNA and used as a nucleobase of hachimoji RNA[1][2].

[Related Catalog]:

Signaling Pathways >> Cell Cycle/DNA Damage >> Nucleoside Antimetabolite/Analog

Research Areas >> Others

[References]

[1]. "Isocytosine". Molecule of the Week. American Chemical Society. Retrieved November 1, 2012.

[2]. Hoshika S, et al. Hachimoji DNA and RNA: A genetic system with eight building blocks. Science. 2019 Feb 22;363(6429):884-887.

Chemical & Physical Properties

[ Density]:
1.5±0.1 g/cm3

[ Boiling Point ]:
393.6±34.0 °C at 760 mmHg

[ Melting Point ]:
275°C

[ Molecular Formula ]:
C₄H₅N₃O

[ Molecular Weight ]:
111.102

[ Flash Point ]:
191.9±25.7 °C

[ Exact Mass ]:
111.043259

[ PSA ]:
72.03000

[ LogP ]:
-1.01

[ Vapour Pressure ]:
0.0±0.9 mmHg at 25°C

[ Index of Refraction ]:
1.668

[ Storage condition ]:
Room temperature.

MSDS

Click to get detail MSDS

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H302-H319

[ Precautionary Statements ]:
P305 + P351 + P338

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Gloves

[ Hazard Codes ]:
Xn:Harmful;

[ Risk Phrases ]:
R22;R36

[ Safety Phrases ]:
S26

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ HS Code ]:
2933599090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2933599090

[ Summary ]:
2933599090. other compounds containing a pyrimidine ring (whether or not hydrogenated) or piperazine ring in the structure. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

Articles

Lead optimization of isocytosine-derived xanthine oxidase inhibitors.

Bioorg. Med. Chem. Lett. 23(3) , 834-8, (2013)

We report our attempts at improving the oral efficacy of low-nanomolar inhibitors of xanthine oxidase from isocytosine series through chemical modifications. Our lead compound had earlier shown good i...

Isocytosine-based inhibitors of xanthine oxidase: Design, synthesis, SAR, PK and in vivo efficacy in rat model of hyperuricemia

Bioorg. Med. Chem. Lett. 22(24) , 7543-6, (2012)

Structure-activity relationship studies were carried out for lead generation following structure-guided design approach from an isocytosine scaffold identified earlier for xanthine oxidase inhibition....

Indirect photochemical transformations of acyclovir and penciclovir in aquatic environments increase ecological risk.

Environ. Toxicol. Chem. 35 , 584-92, (2016)

Acyclovir and penciclovir, 2 antiviral drugs, are increasingly detected in aquatic environments. The present study explores the natural photochemical transformation mechanisms and fate of these drugs,...