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

• ChemBase ID: 173459
• Molecular Formular: C12H20N4O7S
• Molecular Mass: 364.3748
• Monoisotopic Mass: 364.10527
• SMILES: C(NC(=O)[C@@H](NC(=O)CC[C@H](N)C(=O)O)CSC(=O)NC)C(=O)O
• Canonical SMILES: CNC(=O)SC[C@@H](C(=O)NCC(=O)O)NC(=O)CC[C@@H](C(=O)O)N
• InChI: InChI=1S/C12H20N4O7S/c1-14-12(23)24-5-7(10(20)15-4-9(18)19)16-8(17)3-2-6(13)11(21)22/h6-7H,2-5,13H2,1H3,(H,14,23)(H,15,20)(H,16,17)(H,18,19)(H,21,22)/t6-,7-/m0/s1
• InChIKey: ROWIKVIWEBGFSY-BQBZGAKWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-amino-4-{[(1R)-1-[(carboxymethyl)carbamoyl]-2-[(methylcarbamoyl)sulfanyl]ethyl]carbamoyl}butanoic acid
• IUPAC Traditional name: (2S)-2-amino-4-{[(1R)-1-(carboxymethylcarbamoyl)-2-[(methylcarbamoyl)sulfanyl]ethyl]carbamoyl}butanoic acid
• Synonyms: N-[N-L-γ-Glutamyl-S-[(methylamino)carbonyl]-L-cysteinyl]glycine; S-(N-Methylcarbamoyl)glutathione

Database IDs

• CAS Number: 38126-73-7
• PubChem SID: 164229369
• PubChem CID: 115170

CALCULATED PROPERTIES

• Acid pKa: 1.7481362
• H Acceptors: 8
• H Donor: 6
• LogD (pH = 5.5): -7.1123824
• LogD (pH = 7.4): -8.455983
• Log P: -5.206312
• Molar Refractivity: 82.1561 cm^3
• Polarizability: 32.470596 Å^3
• Polar Surface Area: 187.92 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - M294495

A metabolite of the investigational antitumor agent N-methylformamide (NMF).

REFERENCES

• Kaplowitz, N., et al.: J. Pharmacol. Exp. Ther., 212, 240 (1980)
• Lundberg, I., et al.: Toxicology, 22, 1 (1980)
• Gescher, A., et al.: Br. J. Cancer, 45, 843 (1980)
• Pearson, P., et al.: Biochem. Pharmacol., 36, 381 (1980)