disodium (2S)-2-amino-4-{[(1R)-1-[(carboxylatomethyl)carbamoyl]-2-{[5-(2H3)acetamido-2-hydroxyphenyl]sulfanyl}ethyl]carbamoyl}butanoate

• ChemBase ID: 158950
• Molecular Formular: C18H22N4Na2O8S
• Molecular Mass: 500.43382
• Monoisotopic Mass: 500.09537325
• SMILES: c1cc(cc(c1O)SC[C@@H](C(=O)NCC(=O)[O-])NC(=O)CC[C@H](N)C(=O)[O-])NC(=O)C.[Na+].[Na+]
• Canonical SMILES: O=C(N[C@H](C(=O)NCC(=O)[O-])CSc1cc(ccc1O)NC(=O)C)CC[C@@H](C(=O)[O-])N.[Na+].[Na+]
• InChI: InChI=1S/C18H24N4O8S.2Na/c1-9(23)21-10-2-4-13(24)14(6-10)31-8-12(17(28)20-7-16(26)27)22-15(25)5-3-11(19)18(29)30;;/h2,4,6,11-12,24H,3,5,7-8,19H2,1H3,(H,20,28)(H,21,23)(H,22,25)(H,26,27)(H,29,30);;/q;2*+1/p-2/t11-,12-;;/m0../s1
• InChIKey: PFUAJERIABFVCS-AQEKLAMFSA-L

NAMES AND DATABASE IDS

Names

• IUPAC name: disodium (2S)-2-amino-4-{[(1R)-1-[(carboxylatomethyl)carbamoyl]-2-{[5-(^2H₃)acetamido-2-hydroxyphenyl]sulfanyl}ethyl]carbamoyl}butanoate
• IUPAC Traditional name: disodium (2S)-2-amino-4-{[(1R)-1-(carboxylatomethylcarbamoyl)-2-{[5-(^2H₃)acetamido-2-hydroxyphenyl]sulfanyl}ethyl]carbamoyl}butanoate
• Synonyms: L-γ-Glutamyl-S-[5-(acetylamino)-2-hydroxyphenyl]-L-cysteinylglycine Disodium Salt-d3; 3-(Glutathion-S-yl)acetaminophen Disodium Salt-d3; 3-Glutathionylacetaminophen Disodium-d3; Acetaminophen-glutathione Adduct Disodium-d3; Acetaminophen Glutathione-d3 Disodium Salt

Database IDs

• PubChem SID: 162253085
• PubChem CID: 71312750

CALCULATED PROPERTIES

• Acid pKa: 1.7178867
• H Acceptors: 9
• H Donor: 5
• LogD (pH = 5.5): -6.283451
• LogD (pH = 7.4): -7.529813
• Log P: -4.27999
• Molar Refractivity: 132.2092 cm^3
• Polarizability: 42.282333 Å^3
• Polar Surface Area: 213.81 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - A161226

Labelled Acetaminophen Glutathione, a metabolite of Acetaminophen.

REFERENCES

• Chen, C. et al.: Xenobiotica, 30, 1019 (2000)
• Ikeda, H. et al.: Biochem. J., 364, 563 (2000)
• Aleksunes, L. et al.: Toxicol. Sci., 83, 44 (2000)
• Elsby, R. et al.: J. Biol. Chem., 278, 22243 (2000)