(3R)-3-(carbamoylmethyl)-5-methylhexanoic acid

• ChemBase ID: 67631
• Molecular Formular: C9H17NO3
• Molecular Mass: 187.23618
• Monoisotopic Mass: 187.12084341
• SMILES: C(=O)(C[C@H](CC(C)C)CC(=O)N)O
• Canonical SMILES: CC(C[C@@H](CC(=O)O)CC(=O)N)C
• InChI: InChI=1S/C9H17NO3/c1-6(2)3-7(4-8(10)11)5-9(12)13/h6-7H,3-5H2,1-2H3,(H2,10,11)(H,12,13)/t7-/m1/s1
• InChIKey: NPDKTSLVWGFPQG-SSDOTTSWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3R)-3-(carbamoylmethyl)-5-methylhexanoic acid
• IUPAC Traditional name: (3R)-3-(carbamoylmethyl)-5-methylhexanoic acid
• Synonyms: (3R)-3-(2-Amino-2-oxoethyl)-5-methylhexanoic Acid; (R)-3-(2-Amino-2-oxoethyl)-5-methylhexanoic Acid; (R)-(-)-3-(Carbamoylmethyl)-5-methylhexanoic acid; R-(-)-3-(Carbamoylmethyl)-5-methylhexanoic acid

Database IDs

• CAS Number: 181289-33-8
• MDL Number: MFCD09028111
• PubChem SID: 162033366
• PubChem CID: 11084586

CALCULATED PROPERTIES

• Acid pKa: 4.744309
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): -0.122869715
• LogD (pH = 7.4): -1.8998224
• Log P: 0.7023186
• Molar Refractivity: 48.2594 cm^3
• Polarizability: 19.073683 Å^3
• Polar Surface Area: 80.39 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: White Solid
• Melting Point: 120-124°C (dec.)

Safety Information

• Storage Warning: IRRITANT
• TSCA Listed: false

Product Information

• Purity: 95+%

DETAILS

Toronto Research Chemicals - C175955

An impurity of the anti-convulsant (S)-Pregabalin (P704790).

REFERENCES

• Lin, S. et al.: J. Liq. Chrom. Rel. Technol., 19, 2699 (1996)
• Sripathi, S. et al.: ARKIVOC, 10, 266 (1996)