3-formamido-1H-pyrazole-4-carboxamide

• ChemBase ID: 169367
• Molecular Formular: C5H6N4O2
• Molecular Mass: 154.12674
• Monoisotopic Mass: 154.04907545
• SMILES: c1(c(c[nH]n1)C(=O)N)NC=O
• Canonical SMILES: O=CNc1n[nH]cc1C(=O)N
• InChI: InChI=1S/C5H6N4O2/c6-4(11)3-1-8-9-5(3)7-2-10/h1-2H,(H2,6,11)(H2,7,8,9,10)
• InChIKey: MKVXRGIJTKYXPR-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-formamido-1H-pyrazole-4-carboxamide
• IUPAC Traditional name: 3-formamido-1H-pyrazole-4-carboxamide
• Synonyms: 3-Formamidopyrazole-4-carboxamide; Allopurinol Impurity B; 3-(Formylamino)-1H-pyrazole-4-carboxamide

Database IDs

• CAS Number: 22407-20-1
• PubChem SID: 162263499
• PubChem CID: 44819953

CALCULATED PROPERTIES

• Acid pKa: 11.092603
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): -0.43846446
• LogD (pH = 7.4): -0.43853787
• Log P: -0.4384607
• Molar Refractivity: 39.5098 cm^3
• Polarizability: 13.200323 Å^3
• Polar Surface Area: 100.87 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - F696750

An impurity of Allopurinol (A547300) with inhibitory effects on human hypoxanthine phosphoribosyltransferase.

REFERENCES

• Krenitzky, T.A. et al.: J. Biol. Chem., 244, 1263 (1969)