(2S)-2-amino-4-{[(1R)-1-[(carboxymethyl)carbamoyl]-2-{[2-hydroxy(3,3,3-2H3)propyl]sulfanyl}ethyl]carbamoyl}butanoic acid hydrochloride

• ChemBase ID: 171228
• Molecular Formular: C13H24ClN3O7S
• Molecular Mass: 401.86356
• Monoisotopic Mass: 401.1023488
• SMILES: C(CSC[C@H](NC(=O)CC[C@H](N)C(=O)O)C(=O)NCC(=O)O)(O)C.Cl
• Canonical SMILES: CC(CSC[C@@H](C(=O)NCC(=O)O)NC(=O)CC[C@@H](C(=O)O)N)O.Cl
• InChI: InChI=1S/C13H23N3O7S.ClH/c1-7(17)5-24-6-9(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);1H/t7?,8-,9-;/m0./s1
• InChIKey: MSQKVLFWJAOMHM-AYVRSBHTSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-amino-4-{[(1R)-1-[(carboxymethyl)carbamoyl]-2-{[2-hydroxy(3,3,3-^2H₃)propyl]sulfanyl}ethyl]carbamoyl}butanoic acid hydrochloride
• IUPAC Traditional name: (2S)-2-amino-4-{[(1R)-1-(carboxymethylcarbamoyl)-2-{[2-hydroxy(3,3,3-^2H₃)propyl]sulfanyl}ethyl]carbamoyl}butanoic acid hydrochloride
• Synonyms: L-γ-Glutamyl-S-(2-hydroxypropyl)-L-cysteinylgycine-d6; N-[N-L-γ-glutamyl-S-(2-hydroxypropyl)-L-cysteinyl]glycine-d6; S-(2-Hydroxypropyl)glutathione-d6

Database IDs

• PubChem SID: 164227138
• PubChem CID: 71749309

CALCULATED PROPERTIES

• Acid pKa: 1.8081068
• H Acceptors: 8
• H Donor: 6
• LogD (pH = 5.5): -6.8252854
• LogD (pH = 7.4): -8.280335
• Log P: -5.047273
• Molar Refractivity: 84.6802 cm^3
• Polarizability: 33.606052 Å^3
• Polar Surface Area: 179.05 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - H952612

A labelled biliary glutamylcysteinylglycine (GSH) conjugate metabolite of 1,2-dibromo-3-chloropropane (DBCP).

REFERENCES

• Pearson, P.G. et al.: Biochem., 29, 4971 (1990)