(5S)-5-ethyl-5-(4-hydroxyphenyl)-3-methylimidazolidine-2,4-dione

• ChemBase ID: 170726
• Molecular Formular: C12H14N2O3
• Molecular Mass: 234.25116
• Monoisotopic Mass: 234.10044232
• SMILES: N1(C(=O)[C@@](NC1=O)(c1ccc(cc1)O)CC)C
• Canonical SMILES: CC[C@]1(NC(=O)N(C1=O)C)c1ccc(cc1)O
• InChI: InChI=1S/C12H14N2O3/c1-3-12(8-4-6-9(15)7-5-8)10(16)14(2)11(17)13-12/h4-7,15H,3H2,1-2H3,(H,13,17)/t12-/m0/s1
• InChIKey: OQPLORUDZLXXPD-LBPRGKRZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (5S)-5-ethyl-5-(4-hydroxyphenyl)-3-methylimidazolidine-2,4-dione
• IUPAC Traditional name: (5S)-5-ethyl-5-(4-hydroxyphenyl)-3-methylimidazolidine-2,4-dione
• Synonyms: (5S)-5-Ethyl-5-(4-hydroxyphenyl)-3-methyl-2,4-imidazolidinedione; (S)-5-Ethyl-5-(4-hydroxyphenyl)-3-methyl-2,4-imidazolidinedione; (S)-4-Hydroxy Mephenytoin

Database IDs

• CAS Number: 82695-93-0
• PubChem SID: 164226636
• PubChem CID: 40572060

CALCULATED PROPERTIES

• Acid pKa: 9.455566
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 1.3615601
• LogD (pH = 7.4): 1.3578259
• Log P: 1.3616079
• Molar Refractivity: 61.5189 cm^3
• Polarizability: 23.699648 Å^3
• Polar Surface Area: 69.64 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Ethyl Acetate; Methanol
• Apperance: White Solid
• Melting Point: 188-191°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - H944870

The S-enantiomer metabolite of Mephenytoin (M225000).

REFERENCES

• Boobis, A., et al.: Cancer Res., 54, 89 (1994)
• Beresford, A., et al.: Xenobiotica, 27, 159 (1994)
• Zhu, B., et al.: Clin. Pharmacol. Ther., 70, 455 (1994)
• Jerdi, M., et al.: J. Pharm. Biomed. Anal., 35, 1203 (1994)