3-(carbamoyloxy)-2-hydroxy-2-phenylpropyl carbamate

• ChemBase ID: 170518
• Molecular Formular: C11H14N2O5
• Molecular Mass: 254.23926
• Monoisotopic Mass: 254.09027156
• SMILES: c1ccccc1C(COC(=O)N)(COC(=O)N)O
• Canonical SMILES: NC(=O)OCC(c1ccccc1)(COC(=O)N)O
• InChI: InChI=1S/C11H14N2O5/c12-9(14)17-6-11(16,7-18-10(13)15)8-4-2-1-3-5-8/h1-5,16H,6-7H2,(H2,12,14)(H2,13,15)
• InChIKey: VTXNIAJKDLEHGX-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-(carbamoyloxy)-2-hydroxy-2-phenylpropyl carbamate
• IUPAC Traditional name: 3-(carbamoyloxy)-2-hydroxy-2-phenylpropyl carbamate
• Synonyms: 2-Phenyl-1,2,3-propanetriol 1,3-Dicarbamate; 2-Hydroxy-2-phenyl-1,3-propanediyl dicarbamate; W 2292; W 2992; 2-Hydroxy Felbamate

Database IDs

• CAS Number: 109482-32-8
• PubChem SID: 164226428
• PubChem CID: 10400039

CALCULATED PROPERTIES

• Acid pKa: 12.508794
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): 0.02438752
• LogD (pH = 7.4): 0.024384217
• Log P: 0.02438756
• Molar Refractivity: 60.6747 cm^3
• Polarizability: 24.075497 Å^3
• Polar Surface Area: 124.87 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - H942405

A metabolite of the antiepileptic drug Felbamate (F231000).

REFERENCES

• Yang, J.T. et al.: Drug Metab. Disp., 19, 1126 (1991)
• Roller, S.G. et al.: Chem. res. Toxicol., 15, 815 (1991)