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

• ChemBase ID: 169690
• Molecular Formular: C18H29N5O11S2
• Molecular Mass: 555.57976
• Monoisotopic Mass: 555.13049877
• SMILES: [C@@H](CSSC[C@H](NC(=O)CC[C@H](N)C(=O)O)C(=O)NCC(=O)O)(NC(=O)CC[C@H](N)C(=O)O)C(=O)O
• Canonical SMILES: OC(=O)CNC(=O)[C@@H](NC(=O)CC[C@@H](C(=O)O)N)CSSC[C@@H](C(=O)O)NC(=O)CC[C@@H](C(=O)O)N
• InChI: InChI=1S/C18H29N5O11S2/c19-8(16(29)30)1-3-12(24)22-10(15(28)21-5-14(26)27)6-35-36-7-11(18(33)34)23-13(25)4-2-9(20)17(31)32/h8-11H,1-7,19-20H2,(H,21,28)(H,22,24)(H,23,25)(H,26,27)(H,29,30)(H,31,32)(H,33,34)/t8-,9-,10-,11-/m0/s1
• InChIKey: RXKMADLQGPTPJP-NAKRPEOUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-amino-4-{[(1R)-2-{[(2R)-2-[(4S)-4-amino-4-carboxybutanamido]-2-carboxyethyl]disulfanyl}-1-[(carboxymethyl)carbamoyl]ethyl]carbamoyl}butanoic acid
• IUPAC Traditional name: (2S)-2-amino-4-{[(1R)-2-{[(2R)-2-[(4S)-4-amino-4-carboxybutanamido]-2-carboxyethyl]disulfanyl}-1-(carboxymethylcarbamoyl)ethyl]carbamoyl}butanoic acid
• Synonyms: L-γ-Glutamyl-L-cysteinyl-glycine (2-2')-Disulfide -L-γ-glutamyl-L-cysteine; γ-Glu-Cys GSH; L-γ-Glutamyl-L-cysteinyl Glutathione

Database IDs

• CAS Number: 90663-73-3
• PubChem SID: 162263822
• PubChem CID: 12968424

CALCULATED PROPERTIES

• Acid pKa: 1.4214388
• H Acceptors: 13
• H Donor: 9
• LogD (pH = 5.5): -12.701415
• LogD (pH = 7.4): -15.52411
• Log P: -9.022998
• Molar Refractivity: 123.8509 cm^3
• Polarizability: 49.326103 Å^3
• Polar Surface Area: 288.54 Å^2
• Rotatable Bonds: 19
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - G597250

Used in the synthesis of disulfides related to glutathione.

REFERENCES

• Grill, E., et al.: Science, 230, 674 (1985)
• Long, Y., et al.: Int. J. Peptide Protein Res., 47, 42 (1985)
• Clemens, S., et al.: Eur. J. Biochem., 268, 3640 (1985)