3-(aminomethyl)-5-methyl(1,2,3-13C3)hex-5-enoic acid

• ChemBase ID: 165689
• Molecular Formular: C8H15NO2
• Molecular Mass: 160.18816451
• Monoisotopic Mass: 160.12034324
• SMILES: C=C(C[13CH]([13CH2][13C](=O)O)CN)C
• Canonical SMILES: NC[13CH]([13CH2][13C](=O)O)CC(=C)C
• InChI: InChI=1S/C8H15NO2/c1-6(2)3-7(5-9)4-8(10)11/h7H,1,3-5,9H2,2H3,(H,10,11)/i4+1,7+1,8+1
• InChIKey: PASWFMDVINTBNV-DPZTXFNWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-(aminomethyl)-5-methyl(1,2,3-^1^3C₃)hex-5-enoic acid
• IUPAC Traditional name: 3-(aminomethyl)-5-methyl(1,2,3-^1^3C₃)hex-5-enoic acid
• Synonyms: 3-(Aminomethyl)-5-methyl-4-hexenoic Acid-13C3; 5,6-Dehydropregabalin-13C3; rac 5,6-Dehydro Pregabalin-13C3

Database IDs

• PubChem SID: 162259822
• PubChem CID: 71315339

CALCULATED PROPERTIES

• Acid pKa: 4.727944
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): -1.7461946
• LogD (pH = 7.4): -1.692019
• Log P: -1.6928009
• Molar Refractivity: 43.4575 cm^3
• Polarizability: 17.262337 Å^3
• Polar Surface Area: 63.32 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D230057

Labelled 5,6-Dehydropregabalin, an impurity of the anticonvulsant, Pregabalin (P704800).

REFERENCES

• Dousa, M, et al.: J. Pharmac. Biomed. Anal., 53, 717 (2010)