5-(3-hydroxyphenyl)-5-phenylimidazolidine-2,4-dione

• ChemBase ID: 171073
• Molecular Formular: C15H12N2O3
• Molecular Mass: 268.26738
• Monoisotopic Mass: 268.08479225
• SMILES: N1C(=O)C(NC1=O)(c1cc(ccc1)O)c1ccccc1
• Canonical SMILES: Oc1cccc(c1)C1(NC(=O)NC1=O)c1ccccc1
• InChI: InChI=1S/C15H12N2O3/c18-12-8-4-7-11(9-12)15(10-5-2-1-3-6-10)13(19)16-14(20)17-15/h1-9,18H,(H2,16,17,19,20)
• InChIKey: FSPRLRPJSPWQNC-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-(3-hydroxyphenyl)-5-phenylimidazolidine-2,4-dione
• IUPAC Traditional name: 5-(3-hydroxyphenyl)-5-phenylimidazolidine-2,4-dione
• Synonyms: 5-(3-Hydroxyphenyl)-5-phenyl Hydantoin; 5-(3-Hydroxyphenyl)-5-phenyl-2,4-imidazolidinedione; 5-(m-Hydroxyphenyl)-5-phenylhydantoin; 4-(m-Hydroxyphenyl)-4-phenylperhydroimidazole-2,5-dione; 5-(3'-Hydroxyphenyl)-5-phenylhydantoin; m-Hydroxydiphenylhydantoin; m-HPPH; 3-Hydroxy Phenytoin

Database IDs

• CAS Number: 30074-03-4
• PubChem SID: 164226983
• PubChem CID: 91597

CALCULATED PROPERTIES

• Acid pKa: 9.094727
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): 1.8442456
• LogD (pH = 7.4): 1.835704
• Log P: 1.8443551
• Molar Refractivity: 72.1632 cm^3
• Polarizability: 27.738558 Å^3
• Polar Surface Area: 78.43 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - H949300

A major metabolite of Phenytoin, an anticonvulsant.

REFERENCES

• Bowmer, C., et al.: Biochem. Pharmacol., 27, 937 (1978)
• Kober, A., et al.: Mol. Pharmacol., 18, 237 (1978)
• Dasgupta, A., et al.: Ther. Drug Monit., 21, 625 (1978)