5-phenylimidazolidine-2,4-dione

• ChemBase ID: 176585
• Molecular Formular: C9H8N2O2
• Molecular Mass: 176.17202
• Monoisotopic Mass: 176.05857751
• SMILES: C1(=O)NC(C(=O)N1)c1ccccc1
• Canonical SMILES: O=C1NC(=O)NC1c1ccccc1
• InChI: InChI=1S/C9H8N2O2/c12-8-7(10-9(13)11-8)6-4-2-1-3-5-6/h1-5,7H,(H2,10,11,12,13)
• InChIKey: NXQJDVBMMRCKQG-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-phenylimidazolidine-2,4-dione
• IUPAC Traditional name: phenylhydantoin
• Synonyms: 5-Phenyl-2,4-imidazolidinedione; 5-Phenylimidazoline-2,4-dione; NSC 27302; NSC 40885; NSC 51847; 5-Phenylhydantoin; 5-Phenylimidazolidine-2,4-dione

Database IDs

• CAS Number: 89-24-7
• MDL Number: MFCD00037881
• PubChem SID: 164232495
• PubChem CID: 1002

CALCULATED PROPERTIES

• Acid pKa: 9.573963
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 0.48617274
• LogD (pH = 7.4): 0.4833423
• Log P: 0.48620895
• Molar Refractivity: 45.404 cm^3
• Polarizability: 17.562681 Å^3
• Polar Surface Area: 58.2 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Off-White Solid
• Melting Point: 185-186°C

Safety Information

• Storage Condition: Refrigerator

Product Information

• Purity: 95+%

DETAILS

Toronto Research Chemicals - P335000

A metabolite of Mephenytoin. This molecule has been shown to bind to voltage-dependent sodium channels (NVSC) and has antiepileptic properties.

REFERENCES

• Maguire, J., et al.: Eur. J. Pharmacol. 117, 135 (1985)
• Brown, M.L., et al.: J. Med. Chem., 40, 602 (1985)