(2S)-2-amino-4-(benzylsulfanyl)butanoic acid

• ChemBase ID: 161559
• Molecular Formular: C11H15NO2S
• Molecular Mass: 225.3073
• Monoisotopic Mass: 225.08234973
• SMILES: c1(CSCC[C@H](N)C(=O)O)ccccc1
• Canonical SMILES: OC(=O)[C@H](CCSCc1ccccc1)N
• InChI: InChI=1S/C11H15NO2S/c12-10(11(13)14)6-7-15-8-9-4-2-1-3-5-9/h1-5,10H,6-8,12H2,(H,13,14)/t10-/m0/s1
• InChIKey: KIPDMPPOTUGMPW-JTQLQIEISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-amino-4-(benzylsulfanyl)butanoic acid
• IUPAC Traditional name: (2S)-2-amino-4-(benzylsulfanyl)butanoic acid
• Synonyms: L-2-Amino-4-(benzylthio)butyric Acid; S-(Phenylmethyl)-L-homocysteine; 2-Amino-4-benzylthiobutyric Acid; NSC 164657; NSC 206263; S-Benzyl-L-homocysteine

Database IDs

• CAS Number: 7689-60-3
• PubChem SID: 162255694
• PubChem CID: 11736265

CALCULATED PROPERTIES

• Acid pKa: 2.3880856
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): -0.56892246
• LogD (pH = 7.4): -0.57183903
• Log P: -0.5688203
• Molar Refractivity: 62.2478 cm^3
• Polarizability: 24.631622 Å^3
• Polar Surface Area: 63.32 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO
• Apperance: White Solid
• Melting Point: 220-223°C (dec.)

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - B278800

Intermediate in the preparation of L-(+)-Cystathionine.

REFERENCES

• Adang, A., et al.: Biochem. J., 269, 47 (1990)
• Mortell, K., et al.: Bioorg. Med. Chem. Lett., 16, 1138 (1990)
• Grace, C., et al.: J. Med. Chem., 51, 2676 (1990)