(2S)-2-amino-4-{[(1R)-2-{[2-(2-amino-6-oxo-6,7-dihydro-3H-purin-7-yl)(2H4)ethyl]sulfanyl}-1-[(carboxymethyl)carbamoyl]ethyl]carbamoyl}butanoic acid

• ChemBase ID: 169809
• Molecular Formular: C17H24N8O7S
• Molecular Mass: 484.48686
• Monoisotopic Mass: 484.14886615
• SMILES: [C@H](N)(CCC(=O)N[C@@H](CSCCn1c2c([nH]c(nc2=O)N)nc1)C(=O)NCC(=O)O)C(=O)O
• Canonical SMILES: O=C(N[C@H](C(=O)NCC(=O)O)CSCCn1cnc2c1c(=O)nc([nH]2)N)CC[C@@H](C(=O)O)N
• InChI: InChI=1S/C17H24N8O7S/c18-8(16(31)32)1-2-10(26)22-9(14(29)20-5-11(27)28)6-33-4-3-25-7-21-13-12(25)15(30)24-17(19)23-13/h7-9H,1-6,18H2,(H,20,29)(H,22,26)(H,27,28)(H,31,32)(H3,19,23,24,30)/t8-,9-/m0/s1
• InChIKey: OMBANDXHJRVCNU-IUCAKERBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-amino-4-{[(1R)-2-{[2-(2-amino-6-oxo-6,7-dihydro-3H-purin-7-yl)(^2H₄)ethyl]sulfanyl}-1-[(carboxymethyl)carbamoyl]ethyl]carbamoyl}butanoic acid
• IUPAC Traditional name: (2S)-2-amino-4-{[(1R)-2-{[2-(2-amino-6-oxo-3H-purin-7-yl)(^2H₄)ethyl]sulfanyl}-1-(carboxymethylcarbamoyl)ethyl]carbamoyl}butanoic acid
• Synonyms: L-γ-Glutamyl-S-[2-(2-amino-1,6-dihydro-6-oxo-7H-purin-7-yl)ethyl-d4]-L-cysteinylglycine; N-[S-[2-(2-Amino-1,6-dihydro-6-oxo-7H-purin-7-yl)ethyl]-d4-N-L-γ-glutamyl-L-cysteinyl]glycine; S-[2-(N7-guanyl)ethyl-d4]GSH; S-[2-(N7-Guanyl)ethyl]glutathione-d4

Database IDs

• PubChem SID: 162263941
• PubChem CID: 71317177

CALCULATED PROPERTIES

• Acid pKa: 1.6055436
• H Acceptors: 12
• H Donor: 7
• LogD (pH = 5.5): -6.98577
• LogD (pH = 7.4): -8.508156
• Log P: -5.3332143
• Molar Refractivity: 115.7979 cm^3
• Polarizability: 43.67756 Å^3
• Polar Surface Area: 244.12 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - G843802

Labelled S-[2-(N7-Guanyl)ethyl]glutathione, a known DNA adduct formed as a result of glutathione (GSH)-dependent base-substitution mutations caused by the carcinogen ethylene dibromide (EDB).

REFERENCES

• Kim, M.-S. et al.: Che, Res. Toxicol., 11, 311 (1998)
• Ross, M.K. et al.: Chem.-Biol. Inter., 146, 39 (1998)
• Ballering, L.A.P. et al.: Mutagenesis, 13, 61 (1998)