(2S)-6-amino-2-[(2R)-2-[(4S)-4-amino-4-carboxybutanamido]-3-sulfanylpropanamido]hexanoic acid

• ChemBase ID: 169216
• Molecular Formular: C14H26N4O6S
• Molecular Mass: 378.44444
• Monoisotopic Mass: 378.15730557
• SMILES: C(C[C@H](NC(=O)[C@H](CS)NC(=O)CC[C@H](N)C(=O)O)C(=O)O)CCN
• Canonical SMILES: NCCCC[C@@H](C(=O)O)NC(=O)[C@@H](NC(=O)CC[C@@H](C(=O)O)N)CS
• InChI: InChI=1S/C14H26N4O6S/c15-6-2-1-3-9(14(23)24)18-12(20)10(7-25)17-11(19)5-4-8(16)13(21)22/h8-10,25H,1-7,15-16H2,(H,17,19)(H,18,20)(H,21,22)(H,23,24)/t8-,9-,10-/m0/s1
• InChIKey: QVQXRPXVRNLLEO-GUBZILKMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-6-amino-2-[(2R)-2-[(4S)-4-amino-4-carboxybutanamido]-3-sulfanylpropanamido]hexanoic acid
• IUPAC Traditional name: (2S)-6-amino-2-[(2R)-2-[(4S)-4-amino-4-carboxybutanamido]-3-sulfanylpropanamido]hexanoic acid
• Synonyms: N2-(N-L-γ-Glutamyl-L-cysteinyl)-L-lysine; L-γ-Glutamyl-L-cysteinyl-L-lysine

Database IDs

• CAS Number: 128960-73-6
• PubChem SID: 162263348
• PubChem CID: 22854225

CALCULATED PROPERTIES

• Acid pKa: 1.9355053
• H Acceptors: 8
• H Donor: 7
• LogD (pH = 5.5): -6.6183295
• LogD (pH = 7.4): -6.619717
• Log P: -6.6148686
• Molar Refractivity: 90.921 cm^3
• Polarizability: 36.256172 Å^3
• Polar Surface Area: 184.84 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Apperance: Pale Yellow Solid
• Melting Point: 193-196°C

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - G597100

A bifunctional trapping agent (γ-Glutamylcysteinyllysine) is investigated as an alternative of GSH for simultaneous trapping both “hard” and “soft” reactive metabolite.

REFERENCES

• Anderson, M.E., et al.: Methods Enzymology, 113, 549 (1985)
• Adang, A.E.P., et al.: Biochem. J., et al.: 255, 715 (1985)
• Mansoor, M.A., et al.: Anal. Biochem., 200, 218 (1985)
• Schofield, D., et al.: Clin. Sci., 85, 213 (1985)