2-amino-3,4-dihydropyrimidin-4-one

• ChemBase ID: 127891
• Molecular Formular: C4H5N3O
• Molecular Mass: 111.102
• Monoisotopic Mass: 111.0432618
• SMILES: O=c1ccnc(N)[nH]1
• Canonical SMILES: Nc1nccc(=O)[nH]1
• InChI: InChI=1S/C4H5N3O/c5-4-6-2-1-3(8)7-4/h1-2H,(H3,5,6,7,8)
• InChIKey: XQCZBXHVTFVIFE-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-amino-3,4-dihydropyrimidin-4-one
• IUPAC Traditional name: isocytosine
• Synonyms: 2-Amino-4-hydroxypyrimidine; Isocytosine; 2-Aminopyrimidin-4-ol; 2-Aminouracil; Isocytosine

Database IDs

• CAS Number: 100643-25-2; 108-53-2
• EC Number: 203-592-0
• MDL Number: MFCD00023256; MFCD00057557
• PubChem SID: 24895959; 162222208
• PubChem CID: 66950
• CHEBI ID: 55502
• CHEMBL: 56260
• Chemspider ID: 60309
• Wikipedia Title: Isocytosine

CALCULATED PROPERTIES

• Acid pKa: 11.465625
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): -0.8759393
• LogD (pH = 7.4): -0.7867623
• Log P: -0.7854628
• Molar Refractivity: 28.1485 cm^3
• Polarizability: 10.264828 Å^3
• Polar Surface Area: 67.48 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22-36
• Safety Statements: 26
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H319
• GHS Precautionary statements: P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥99%; 95+%

DETAILS

Sigma Aldrich - I2127

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.