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I2127

Sigma-Aldrich

Isocytosine

≥99%

Synonym(s):

2-Amino-4-hydroxypyrimidine, 2-Aminouracil

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About This Item

Empirical Formula (Hill Notation):
C4H5N3O
CAS Number:
108-53-2
Molecular Weight:
111.10
EC Number:
203-592-0
MDL number:
MFCD00057557
UNSPSC Code:
41106305
PubChem Substance ID:
24895959

biological source

synthetic (organic)

assay

≥99%

form

powder

solubility

acetic acid: 50 mg/mL, clear, colorless

SMILES string

NC1=NC=CC(=O)N1

InChI

1S/C4H5N3O/c5-4-6-2-1-3(8)7-4/h1-2H,(H3,5,6,7,8)

InChI key

XQCZBXHVTFVIFE-UHFFFAOYSA-N

Application

Isocytosine (2-aminouracil) is an isomer of cytosine used in physical chemical studies involving metal complex binding, hydrogen-bonding, and tautomerism and proton transfer effects in nucleobases.

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H302,H319

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Stefan Geschwindner et al.
Journal of medicinal chemistry, 50(24), 5903-5911 (2007-11-08)
Fragment-based lead generation was applied to find novel small-molecule inhibitors of beta-secretase (BACE-1), a key target for the treatment of Alzheimer's disease. Fragment hits coming from a 1D NMR screen were characterized by BIAcore, and the most promising compounds were
Chandrika B-Rao et al.
Bioorganic & medicinal chemistry, 20(9), 2930-2939 (2012-04-10)
In recent years, xanthine oxidase has emerged as an important target not only for gout but also for cardiovascular and metabolic disorders involving hyperuricemia. Contrary to popular belief, recent clinical trials with uricosurics have demonstrated that enhanced excretion of uric
T K Ha et al.
Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy, 57(1), 55-72 (2001-02-24)
Results of a search for correlations between typical group mode frequencies and conformation of -OH and =NH substituents is reported. The study is based on quantum chemical data (HF/6-31G (d, p) and MP2 (full)/6-31G (d, p) approximations) of 13 isomers
T M Chin et al.
Biochemistry, 39(40), 12457-12464 (2000-10-04)
The formation of a DNA "paper-clip" type triple helix (triplex) with a common sequence 5'-d-(TC)(3)T(a)()(CT)(3)C(b)()(AG)(3) (a and b = 0-4) was studied by UV thermal melting experiments and CD spectra. These DNA oligomers form triplexes and duplexes under slightly acidic
Rumyana I Bakalska et al.
Journal of molecular modeling, 18(12), 5133-5146 (2012-07-11)
An experimental and theoretical investigation was performed to study the photostability of cytosine and isocytosine. The experimental UV irradiation of acetonitrile solutions of the two compounds showed that the amino-oxo tautomer of cytosine is photostable while the amino-oxo tautomer of
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