(2R)-2-amino-4-[butyl(imino)oxo-λ6-sulfanyl]butanoic acid

• ChemBase ID: 163179
• Molecular Formular: C8H18N2O3S
• Molecular Mass: 222.30512
• Monoisotopic Mass: 222.10381345
• SMILES: C(CS(=O)(=N)CC[C@@H](N)C(=O)O)CC
• Canonical SMILES: CCCCS(=O)(=N)CC[C@H](C(=O)O)N
• InChI: InChI=1S/C8H18N2O3S/c1-2-3-5-14(10,13)6-4-7(9)8(11)12/h7,10H,2-6,9H2,1H3,(H,11,12)/t7-,14?/m1/s1
• InChIKey: KJQFBVYMGADDTQ-SKKCEABJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-2-amino-4-[butyl(imino)oxo-λ^6-sulfanyl]butanoic acid
• IUPAC Traditional name: (2R)-2-amino-4-[butyl(imino)oxo-λ^6-sulfanyl]butanoic acid
• Synonyms: (2S)-2-Amino-4-(S-butylsulfonimidoyl)butanoic Acid; D-Buthionine Sulfoximine; D-Buthionine-(S,R)-sulfoximine

Database IDs

• CAS Number: 113158-69-3
• PubChem SID: 162257314
• PubChem CID: 6603737

CALCULATED PROPERTIES

• Acid pKa: 2.181531
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -2.9740744
• LogD (pH = 7.4): -2.9773746
• Log P: -2.9709322
• Molar Refractivity: 54.0074 cm^3
• Polarizability: 22.389696 Å^3
• Polar Surface Area: 104.24 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - B690265

A potent and specific inhibitor of alpha-glutamylcysteine synthetase.

REFERENCES

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• Griffith, O.W., Methods in Enzymology, 77, 59 (1979)
• Slivka, A., et al.: J. of Neurochemistry, 50, 5, 1391 (1979)
• Du, D-L, et al.: Cancer Research, 50, 4038 (1979)
• Sandor, V., et al.: J. of