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

• ChemBase ID: 173798
• Molecular Formular: C13H23N3O7S
• Molecular Mass: 365.40262
• Monoisotopic Mass: 365.12567109
• SMILES: OCC(SC[C@H](NC(=O)CC[C@H](N)C(=O)O)C(=O)NCC(=O)O)C
• Canonical SMILES: OCC(SC[C@@H](C(=O)NCC(=O)O)NC(=O)CC[C@@H](C(=O)O)N)C
• InChI: InChI=1S/C13H23N3O7S/c1-7(5-17)24-6-9(12(21)15-4-11(19)20)16-10(18)3-2-8(14)13(22)23/h7-9,17H,2-6,14H2,1H3,(H,15,21)(H,16,18)(H,19,20)(H,22,23)/t7?,8-,9-/m0/s1
• InChIKey: QFCICQXODPSLQK-NPPUSCPJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-amino-4-{[(1R)-1-[(carboxymethyl)carbamoyl]-2-[(1-hydroxypropan-2-yl)sulfanyl]ethyl]carbamoyl}butanoic acid
• IUPAC Traditional name: (2S)-2-amino-4-{[(1R)-1-(carboxymethylcarbamoyl)-2-[(1-hydroxypropan-2-yl)sulfanyl]ethyl]carbamoyl}butanoic acid
• Synonyms: N-[N-L-γ-glutamyl-S-(1-methyl-2-hydroxyethyl)-L-cysteinyl]glycine; S-(1-Methyl-2-hydroxyethyl)glutathione(Mixture of Diastereomers); L-γ-Glutamyl-S-(1-methyl-2-hydroxyethyl)-L-cysteinylgycine

Database IDs

• PubChem SID: 164229708
• PubChem CID: 71749314

CALCULATED PROPERTIES

• Acid pKa: 1.8082718
• H Acceptors: 8
• H Donor: 6
• LogD (pH = 5.5): -6.6920714
• LogD (pH = 7.4): -8.241018
• Log P: -5.046325
• Molar Refractivity: 84.6524 cm^3
• Polarizability: 33.606895 Å^3
• Polar Surface Area: 179.05 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - M312635

A glutamylcysteinylglycine (GSH) derivative.