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

• ChemBase ID: 170564
• Molecular Formular: C12H22ClN3O7S
• Molecular Mass: 387.83698
• Monoisotopic Mass: 387.08669874
• SMILES: OCCSC[C@H](NC(=O)CC[C@H](N)C(=O)O)C(=O)NCC(=O)O.Cl
• Canonical SMILES: OCCSC[C@@H](C(=O)NCC(=O)O)NC(=O)CC[C@@H](C(=O)O)N.Cl
• InChI: InChI=1S/C12H21N3O7S.ClH/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);1H/t7-,8-;/m0./s1
• InChIKey: QRFINCSKCRZION-WSZWBAFRSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• PubChem SID: 164226474
• PubChem CID: 71749038

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 to Off-White Solid
• Melting Point: 176-178°C

Safety Information

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

DETAILS

Toronto Research Chemicals - H942155

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)