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

• ChemBase ID: 169689
• Molecular Formular: C20H32N6O12S2
• Molecular Mass: 612.63108
• Monoisotopic Mass: 612.15196249
• SMILES: C(NC(=O)[C@H](CSSC[C@H](NC(=O)[C@H](CCC(=O)O)N)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)NCC(=O)O)NC(=O)[C@H](CCC(=O)O)N
• InChI: InChI=1S/C20H32N6O12S2/c21-9(2-4-14(28)29)17(34)26-12(19(36)24-6-16(32)33)8-40-39-7-11(18(35)23-5-15(30)31)25-13(27)3-1-10(22)20(37)38/h9-12H,1-8,21-22H2,(H,23,35)(H,24,36)(H,25,27)(H,26,34)(H,28,29)(H,30,31)(H,32,33)(H,37,38)/t9-,10-,11-,12-/m0/s1
• InChIKey: JRBLIKMXDVZVGD-BJDJZHNGSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 119290-90-3
• PubChem SID: 162263821
• PubChem CID: 71317106

CALCULATED PROPERTIES

• Acid pKa: 1.7163689
• H Acceptors: 14
• H Donor: 10
• LogD (pH = 5.5): -13.548895
• LogD (pH = 7.4): -16.615559
• Log P: -10.193123
• Molar Refractivity: 136.6544 cm^3
• Polarizability: 54.28691 Å^3
• Polar Surface Area: 317.64 Å^2
• Rotatable Bonds: 21
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - G597200

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)