(2S)-2-amino-4-{[(1R)-1-[(carboxymethyl)carbamoyl]-2-(ethylsulfanyl)ethyl]carbamoyl}butanoic acid

• ChemBase ID: 168586
• Molecular Formular: C12H21N3O6S
• Molecular Mass: 335.37664
• Monoisotopic Mass: 335.11510641
• SMILES: C(NC(=O)[C@@H](NC(=O)CC[C@H](N)C(=O)O)CSCC)C(=O)O
• Canonical SMILES: CCSC[C@@H](C(=O)NCC(=O)O)NC(=O)CC[C@@H](C(=O)O)N
• InChI: InChI=1S/C12H21N3O6S/c1-2-22-6-8(11(19)14-5-10(17)18)15-9(16)4-3-7(13)12(20)21/h7-8H,2-6,13H2,1H3,(H,14,19)(H,15,16)(H,17,18)(H,20,21)/t7-,8-/m0/s1
• InChIKey: HMFDVPSBWOHOAP-YUMQZZPRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-amino-4-{[(1R)-1-[(carboxymethyl)carbamoyl]-2-(ethylsulfanyl)ethyl]carbamoyl}butanoic acid
• IUPAC Traditional name: (2S)-2-amino-4-{[(1R)-1-(carboxymethylcarbamoyl)-2-(ethylsulfanyl)ethyl]carbamoyl}butanoic acid
• Synonyms: L-γ-Glutamyl-S-ethyl-L-cysteinyl-glycine; N-[1-[(Carboxymethyl)carbamoyl]-2-(ethylthio)ethyl]glutamine; N-(S-Ethyl-N-L-γ-glutamyl-L-cysteinyl)-; Ethylglutathione; S-Ethyl-GSH; S-Ethylglutathione; S-Ethylglutathione

Database IDs

• CAS Number: 24425-52-3
• PubChem SID: 162262718
• PubChem CID: 107650

CALCULATED PROPERTIES

• Acid pKa: 1.8136082
• H Acceptors: 7
• H Donor: 5
• LogD (pH = 5.5): -5.7768455
• LogD (pH = 7.4): -7.378531
• Log P: -4.2212195
• Molar Refractivity: 78.5637 cm^3
• Polarizability: 31.09658 Å^3
• Polar Surface Area: 158.82 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: White to Off-White Solid
• Melting Point: 150-153°C

Safety Information

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

DETAILS

Toronto Research Chemicals - E918500

An inhibitor of the enzyme Glyoxalase 1.

REFERENCES

• Vince, R. and Wadd, W.B.: Biochemical and Biophysical Res. Commun., 35, 5 (1969)
• Vegvari, A., et al.: ChemBioChem, 3(1969)
• 1117 (2002)