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

• ChemBase ID: 155304
• Molecular Formular: C6H11NO2
• Molecular Mass: 129.15704
• Monoisotopic Mass: 129.0789786
• SMILES: C=C[C@H](CCC(=O)O)N
• 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-/m1/s1
• InChIKey: PJDFLNIOAUIZSL-RXMQYKEDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S)-4-aminohex-5-enoic acid
• IUPAC Traditional name: sabril (TN)
• Synonyms: (4S)-4-Amino-5-hexenoic Acid; (+)-γ-Vinyl GABA; (S)-4-Amino-5-hexenoic Acid; 4(S)-Amino-5-hexenoic Acid; RMI 71890; S-(+)-Vigabatrin; (S)-Vigabatrin; S(+)-γ-Vinyl GABA; S(+)-4-Aminohexenoic acid; S(+)-γ-Vigabatrin; (S)-4-aminohex-5-enoic acid

Database IDs

• CAS Number: 74046-07-4
• MDL Number: MFCD00274076
• PubChem SID: 24900710; 162249442
• PubChem CID: 10219440

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

PROPERTIES

Physical Property

• Solubility: ethanol: soluble; H2O: >20 mg/mL
• Apperance: off-white solid
• Optical Rotation: [α]/D +11.8°, c = 2.5 in H2O(lit.)

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: 98%
• Empirical Formula (Hill Notation): C6H11NO2

DETAILS

Sigma Aldrich - V113

Biochem/physiol Actions
GABA transaminase inhibitor; anti-convulsant.
Caution
Hygroscopic

Toronto Research Chemicals - V253000

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)