1-[(E)-[(4-hydroxy-5-nitrofuran-2-yl)methylidene]amino]imidazolidine-2,4-dione

• ChemBase ID: 170979
• Molecular Formular: C8H6N4O6
• Molecular Mass: 254.15644
• Monoisotopic Mass: 254.02873393
• SMILES: c1(cc(oc1[N+](=O)[O-])/C=N/N1CC(=O)NC1=O)O
• Canonical SMILES: O=C1NC(=O)N(C1)/N=C/c1cc(c(o1)[N+](=O)[O-])O
• InChI: InChI=1S/C8H6N4O6/c13-5-1-4(18-7(5)12(16)17)2-9-11-3-6(14)10-8(11)15/h1-2,13H,3H2,(H,10,14,15)/b9-2+
• InChIKey: FVAPZVJUBYDZAT-XNWCZRBMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[(E)-[(4-hydroxy-5-nitrofuran-2-yl)methylidene]amino]imidazolidine-2,4-dione
• IUPAC Traditional name: 1-[(E)-[(4-hydroxy-5-nitrofuran-2-yl)methylidene]amino]imidazolidine-2,4-dione
• Synonyms: 1-[[(4-Hydroxy-5-nitro-2-furanyl)methylene]amino]-2,4-imidazolidinedione; 4-Hydroxy Nitrofurantoin

Database IDs

• CAS Number: 76644-41-2
• PubChem SID: 164226889
• PubChem CID: 9576892

CALCULATED PROPERTIES

• Acid pKa: 4.1113687
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): -1.5513054
• LogD (pH = 7.4): -1.7707525
• Log P: -0.5250153
• Molar Refractivity: 55.095 cm^3
• Polarizability: 19.953566 Å^3
• Polar Surface Area: 140.96 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - H948665

A metabolite of Nitrofurantoin (N493850).

REFERENCES

• Jonen, H.G., et al.: Drug Metab. Dispos., 8 446 (1980)
• Streeter, A.J., et al.: Pharmacology, 36, 283 (1980)