(2S)-2-amino-4-{[(1R)-2-[(5-amino-2-hydroxyphenyl)sulfanyl]-1-[(carboxymethyl)carbamoyl]ethyl]carbamoyl}butanoic acid

• ChemBase ID: 165848
• Molecular Formular: C16H22N4O7S
• Molecular Mass: 414.43348
• Monoisotopic Mass: 414.12092006
• SMILES: c1cc(cc(c1O)SC[C@@H](C(=O)NCC(=O)O)NC(=O)CC[C@H](N)C(=O)O)N
• Canonical SMILES: O=C(N[C@H](C(=O)NCC(=O)O)CSc1cc(N)ccc1O)CC[C@@H](C(=O)O)N
• InChI: InChI=1S/C16H22N4O7S/c17-8-1-3-11(21)12(5-8)28-7-10(15(25)19-6-14(23)24)20-13(22)4-2-9(18)16(26)27/h1,3,5,9-10,21H,2,4,6-7,17-18H2,(H,19,25)(H,20,22)(H,23,24)(H,26,27)/t9-,10-/m0/s1
• InChIKey: PYIOCFGATFKYGA-UWVGGRQHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-amino-4-{[(1R)-2-[(5-amino-2-hydroxyphenyl)sulfanyl]-1-[(carboxymethyl)carbamoyl]ethyl]carbamoyl}butanoic acid
• IUPAC Traditional name: (2S)-2-amino-4-{[(1R)-2-[(5-amino-2-hydroxyphenyl)sulfanyl]-1-(carboxymethylcarbamoyl)ethyl]carbamoyl}butanoic acid
• Synonyms: N-[S-(5-Amino-2-hydroxyphenyl)-N-L-γ-glutamyl-L-cysteinyl]glycine; Desacetyl Acetaminophen Glutathione

Database IDs

• CAS Number: 129762-76-1
• PubChem SID: 162259981
• PubChem CID: 182959

CALCULATED PROPERTIES

• Acid pKa: 1.7344706
• H Acceptors: 9
• H Donor: 7
• LogD (pH = 5.5): -6.006441
• LogD (pH = 7.4): -7.4410934
• Log P: -5.518089
• Molar Refractivity: 100.3724 cm^3
• Polarizability: 38.739834 Å^3
• Polar Surface Area: 205.07 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - D288400

The hepatic metabolite of p-Aminophenol. The aminophenol glutathione S-conjugates formed induce p-Aminophenol nephrotoxicity by a pathway dependent on γ-glutamyl transpeptidase.

REFERENCES

• Eckert, K.G., et al.: Xenobiotica, 20, 333 (1990)
• Klos, C., et al.: Toxicol. Applied Pharmacol., 115, 98 (1990)