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

• ChemBase ID: 168534
• Molecular Formular: C22H36N6O12S2
• Molecular Mass: 640.68424
• Monoisotopic Mass: 640.18326262
• SMILES: [C@H](N)(CCC(=O)N[C@@H](CSCCSC[C@H](NC(=O)CC[C@H](N)C(=O)O)C(=O)NCC(=O)O)C(=O)NCC(=O)O)C(=O)O
• Canonical SMILES: O=C(N[C@H](C(=O)NCC(=O)O)CSCCSC[C@@H](C(=O)NCC(=O)O)NC(=O)CC[C@@H](C(=O)O)N)CC[C@@H](C(=O)O)N
• InChI: InChI=1S/C22H36N6O12S2/c23-11(21(37)38)1-3-15(29)27-13(19(35)25-7-17(31)32)9-41-5-6-42-10-14(20(36)26-8-18(33)34)28-16(30)4-2-12(24)22(39)40/h11-14H,1-10,23-24H2,(H,25,35)(H,26,36)(H,27,29)(H,28,30)(H,31,32)(H,33,34)(H,37,38)(H,39,40)/t11-,12-,13-,14-/m0/s1
• InChIKey: QBLFRDYFTLRVBW-XUXIUFHCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-amino-4-{[(1R)-2-[(2-{[(2R)-2-[(4S)-4-amino-4-carboxybutanamido]-2-[(carboxymethyl)carbamoyl]ethyl]sulfanyl}ethyl)sulfanyl]-1-[(carboxymethyl)carbamoyl]ethyl]carbamoyl}butanoic acid
• IUPAC Traditional name: S,S'-ethylenebis(glutathione)
• Synonyms: 2,2'-(1,2-Ethanediyl)bis[L-γ-glutamyl-L-cysteinylglycine; S,S'-Ethylenebis(glutathione)

Database IDs

• PubChem SID: 162262666
• PubChem CID: 71316571

CALCULATED PROPERTIES

• Acid pKa: 1.5104586
• H Acceptors: 14
• H Donor: 10
• LogD (pH = 5.5): -12.922275
• LogD (pH = 7.4): -16.0411
• Log P: -9.65309
• Molar Refractivity: 145.9692 cm^3
• Polarizability: 57.867718 Å^3
• Polar Surface Area: 317.64 Å^2
• Rotatable Bonds: 23
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - E917460

S,S'-Ethylenebis(glutathione) is a haloethane-glutathione conjugate formed via GSH transferases. S,S'-Ethylenebis(glutathione) formation is used to study the polymorphism in glutathione conjugation activity of human erythrocytes towards ethylene dibromide

REFERENCES

• Ploemen, J.H.T.M. et al.: Biochim. Biophys. Acta Gen. Subj., 1243, 469 (1995)
• Thomas, C. et al.: Biochem. Pharmacol., 61, 595 (1995)