3-(aminomethyl)-5-methylhex-5-enoic acid

• ChemBase ID: 165688
• Molecular Formular: C8H15NO2
• Molecular Mass: 157.2102
• Monoisotopic Mass: 157.11027873
• SMILES: C=C(CC(CC(=O)O)CN)C
• Canonical SMILES: NCC(CC(=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)
• InChIKey: PASWFMDVINTBNV-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-(aminomethyl)-5-methylhex-5-enoic acid
• IUPAC Traditional name: 3-(aminomethyl)-5-methylhex-5-enoic acid
• Synonyms: 3-(Aminomethyl)-5-methyl-5-hexenoic Acid; 5,6-Dehydropregabalin; rac 5,6-Dehydro Pregabalin

Database IDs

• CAS Number: 1136478-30-2
• PubChem SID: 162259821
• PubChem CID: 25256213

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 - D230055

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

REFERENCES

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