(4R)-4-aminohex-5-enoic acid

• ChemBase ID: 179450
• Molecular Formular: C6H11NO2
• Molecular Mass: 129.15704
• Monoisotopic Mass: 129.0789786
• SMILES: C(C[C@H](C=C)N)C(=O)O
• Canonical SMILES: N[C@@H](C=C)CCC(=O)O
• InChI: InChI=1S/C6H11NO2/c1-2-5(7)3-4-6(8)9/h2,5H,1,3-4,7H2,(H,8,9)/t5-/m0/s1
• InChIKey: PJDFLNIOAUIZSL-YFKPBYRVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4R)-4-aminohex-5-enoic acid
• IUPAC Traditional name: (4R)-4-aminohex-5-enoic acid
• Synonyms: (4R)-4-Amino-5-hexenoic Acid; (R)-4-Amino-5-hexenoic Acid; (-)-γ-Vinyl GABA; R-(-)-Vigabatrin; RMI 71894; ent-Vigabatrin; (R)-Vigabatrin

Database IDs

• CAS Number: 77162-51-7
• PubChem SID: 164235360
• PubChem CID: 157018

CALCULATED PROPERTIES

• Acid pKa: 4.608113
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): -2.1360347
• LogD (pH = 7.4): -2.0948071
• Log P: -2.0949147
• Molar Refractivity: 34.2907 cm^3
• Polarizability: 13.588985 Å^3
• Polar Surface Area: 63.32 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - V252995

The R-enantiomer of Vigabatrin, a novel antiepileptic drug. Antidepressant; antipsychotic; anxiolytic.

REFERENCES

• Vajda, F., et al.: Clin. Neurosci., 7, 88 (2000)
• Beghi, E., et al.: Lancet. Neurol., 3, 618 (2000)
• Sagirli, O., et al.: J. Pharmaceut. Biomed., 42, 618 (2000)