(2S)-2-[(ethoxycarbonyl)amino]-2,3-dimethylbutanoic acid

• ChemBase ID: 168309
• Molecular Formular: C9H17NO4
• Molecular Mass: 203.23558
• Monoisotopic Mass: 203.11575803
• SMILES: C(=O)(N[C@](C(C)C)(C)C(=O)O)OCC
• Canonical SMILES: CCOC(=O)N[C@](C(=O)O)(C(C)C)C
• InChI: InChI=1S/C9H17NO4/c1-5-14-8(13)10-9(4,6(2)3)7(11)12/h6H,5H2,1-4H3,(H,10,13)(H,11,12)/t9-/m0/s1
• InChIKey: RIILJEXEFLLELQ-VIFPVBQESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-[(ethoxycarbonyl)amino]-2,3-dimethylbutanoic acid
• IUPAC Traditional name: (2S)-2-[(ethoxycarbonyl)amino]-2,3-dimethylbutanoic acid
• Synonyms: (S)-N-Ethoxycarbonyl-α-methylvaline; N-Ethoxycarbonyl α-Methyl-L-valine

Database IDs

• CAS Number: 952577-51-4
• PubChem SID: 162262441
• PubChem CID: 23583348

CALCULATED PROPERTIES

• Acid pKa: 4.018381
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 0.044652857
• LogD (pH = 7.4): -1.6119368
• Log P: 1.5364954
• Molar Refractivity: 50.0222 cm^3
• Polarizability: 19.816086 Å^3
• Polar Surface Area: 75.63 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - E890495

Methylvaline derivative. Used in the preparation of medicinal and herbicidal agents.

REFERENCES

• Cronin, J., et al.: Science, 275, 951 (1997)
• Podlech, J., et al.: Cell Mol. Life. Sci., 58, 44 (1997)
• Lee, S., et al.: J. Biol. Chem., 278, 46649 (1997)