3-[amino(13C)methyl]-5-methyl(1,2-13C2)hex-4-enoic acid

• ChemBase ID: 165687
• Molecular Formular: C8H15NO2
• Molecular Mass: 160.18816451
• Monoisotopic Mass: 160.12034324
• SMILES: C(=CC([13CH2][13C](=O)O)[13CH2]N)(C)C
• Canonical SMILES: N[13CH2]C(C=C(C)C)[13CH2][13C](=O)O
• InChI: InChI=1S/C8H15NO2/c1-6(2)3-7(5-9)4-8(10)11/h3,7H,4-5,9H2,1-2H3,(H,10,11)/i4+1,5+1,8+1
• InChIKey: RILHQHHDJPATCS-LGMPQVEQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-[amino(^1^3C)methyl]-5-methyl(1,2-^1^3C₂)hex-4-enoic acid
• IUPAC Traditional name: 3-[amino(^1^3C)methyl]-5-methyl(1,2-^1^3C₂)hex-4-enoic acid
• Synonyms: 3-(Aminomethyl)-5-methyl-4-hexenoic Acid-13C3; 4,5-Dehydropregabalin-13C3; rac 4,5-Dehydro Pregabalin-13C3

Database IDs

• PubChem SID: 162259820
• PubChem CID: 71315338

CALCULATED PROPERTIES

• Lipinski's Rule of Five: true
• Acid pKa: 4.723635
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): -1.8036127
• LogD (pH = 7.4): -1.7499716
• Log P: -1.7507168
• Molar Refractivity: 44.53 cm^3
• Polarizability: 17.262337 Å^3
• Polar Surface Area: 63.32 Å^2
• Rotatable Bonds: 4

DETAILS

Toronto Research Chemicals - D230052

Labelled 4,5-Dehydropregabalin, an impurity of the anticonvulsant, Pregabalin (P704800).

REFERENCES

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