(2S)-2-amino-4-[(S)-imino(methyl)oxo-λ6-sulfanyl]butanoic acid

• ChemBase ID: 172855
• Molecular Formular: C5H12N2O3S
• Molecular Mass: 180.22538
• Monoisotopic Mass: 180.05686325
• SMILES: [S@@](=N)(=O)(CC[C@H](N)C(=O)O)C
• Canonical SMILES: OC(=O)[C@H](CC[S@](=O)(=N)C)N
• InChI: InChI=1S/C5H12N2O3S/c1-11(7,10)3-2-4(6)5(8)9/h4,7H,2-3,6H2,1H3,(H,8,9)/t4-,11-/m0/s1
• InChIKey: SXTAYKAGBXMACB-AUIPBDMJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-amino-4-[(S)-imino(methyl)oxo-λ^6-sulfanyl]butanoic acid
• IUPAC Traditional name: 2S,5S-methionine sulfoximine
• Synonyms: (2S)-2-Amino-4-[[S(S)]-S-methylsulfonimidoyl]butanoic Acid; [S-(R*,R*)]-2-Amino-4-(S-methylsulfonimidoyl)butanoic Acid; (S)-L-S-(3-amino-3-carboxypropyl)-S-methylsulfoximine; L-Methionine [S]-Sulfoximine

Database IDs

• CAS Number: 21752-32-9
• PubChem SID: 164228765
• PubChem CID: 24755488

CALCULATED PROPERTIES

• Acid pKa: 1.8865596
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -4.447861
• LogD (pH = 7.4): -4.453787
• Log P: -4.446533
• Molar Refractivity: 40.2168 cm^3
• Polarizability: 16.919283 Å^3
• Polar Surface Area: 104.24 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: White to Off-White Solid
• Melting Point: 218-226°C (dec.)

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - M260510

It is the diastereoisomer of L-Methionine [R,S]-Sulfoximine (M260500) that inhibits glutamine synthetase.

REFERENCES

• Wilson, J., et al.: J. Exp. Biol., 203, 2297 (2000)
• Ip, Y., et al.: J. Exp. Biol., 208, 1993 (2000)