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

• ChemBase ID: 170565
• Molecular Formular: C12H21N3O7S
• Molecular Mass: 351.37604
• Monoisotopic Mass: 351.11002103
• SMILES: OCCSC[C@H](NC(=O)CC[C@H](N)C(=O)O)C(=O)NCC(=O)O
• Canonical SMILES: OCCSC[C@@H](C(=O)NCC(=O)O)NC(=O)CC[C@@H](C(=O)O)N
• InChI: InChI=1S/C12H21N3O7S/c13-7(12(21)22)1-2-9(17)15-8(6-23-4-3-16)11(20)14-5-10(18)19/h7-8,16H,1-6,13H2,(H,14,20)(H,15,17)(H,18,19)(H,21,22)/t7-,8-/m0/s1
• InChIKey: UUZCUSQQEJSIHR-YUMQZZPRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-amino-4-{[(1R)-1-[(carboxymethyl)carbamoyl]-2-[(2-hydroxyethyl)sulfanyl]ethyl]carbamoyl}butanoic acid
• IUPAC Traditional name: S-(2-hydroxyethyl)glutathione
• Synonyms: L-γ-Glutamyl-S-(2-hydroxyethyl)-L-cysteinylglycine; L-N-[1-[(Carboxymethyl)carbamoyl]-2-[(2-hydroxyethyl)thio]ethyl]glutamine; N-[N-L-γ-Glutamyl-S-(2-hydroxyethyl)-L-cysteinyl]glycine; S-(β-Hydroxyethyl)glutathione; S-(2-Hydroxyethyl)glutathione

Database IDs

• CAS Number: 28747-20-8
• PubChem SID: 164226475
• PubChem CID: 5460887

CALCULATED PROPERTIES

• Acid pKa: 1.8097548
• H Acceptors: 8
• H Donor: 6
• LogD (pH = 5.5): -7.148097
• LogD (pH = 7.4): -8.660302
• Log P: -5.4471035
• Molar Refractivity: 80.2614 cm^3
• Polarizability: 31.793434 Å^3
• Polar Surface Area: 179.05 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: White Solid

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Storage Warning: Very Hygroscopic

DETAILS

Toronto Research Chemicals - H942156

A glutathione derivative as inhibitor of glutathione S-transferase.

REFERENCES

• Dirr, H., et al.: Eur. J. Biochem., 196, 693 (1991)
• Oakley, A., et al.: J. Mol. Biol., 274, 84 (1991)
• Alcaro, S., et al.: Bioorg. Med. Chem., 13, 3371 (1991)