sodium (2R)-2-acetamido-3-[(5-acetamido-2-hydroxyphenyl)sulfanyl]propanoate

• ChemBase ID: 159217
• Molecular Formular: C13H15N2NaO5S
• Molecular Mass: 334.32337
• Monoisotopic Mass: 334.05993687
• SMILES: c1(ccc(cc1SC[C@@H](C(=O)[O-])NC(=O)C)NC(=O)C)O.[Na+]
• Canonical SMILES: CC(=O)Nc1ccc(c(c1)SC[C@@H](C(=O)[O-])NC(=O)C)O.[Na+]
• InChI: InChI=1S/C13H16N2O5S.Na/c1-7(16)14-9-3-4-11(18)12(5-9)21-6-10(13(19)20)15-8(2)17;/h3-5,10,18H,6H2,1-2H3,(H,14,16)(H,15,17)(H,19,20);/q;+1/p-1/t10-;/m0./s1
• InChIKey: JKIDIVFUGFKUBH-PPHPATTJSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium (2R)-2-acetamido-3-[(5-acetamido-2-hydroxyphenyl)sulfanyl]propanoate
• IUPAC Traditional name: sodium (2R)-2-acetamido-3-[(5-acetamido-2-hydroxyphenyl)sulfanyl]propanoate
• Synonyms: Paracetamol Mercapturate, Sodium Salt, Acetaminophen Mercaturate; APAP-CYS; 3-(N-Acetyl-L-cystein-S-yl) Acetaminophen Sodium Salt

Database IDs

• CAS Number: 52372-86-8
• PubChem SID: 162253352
• PubChem CID: 46779971

CALCULATED PROPERTIES

• Acid pKa: 3.2300014
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -2.2614436
• LogD (pH = 7.4): -3.4598172
• Log P: -0.012275034
• Molar Refractivity: 89.9246 cm^3
• Polarizability: 29.794975 Å^3
• Polar Surface Area: 118.56 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: Red Solid
• Melting Point: >170°C (dec.)

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - A172100

APAP-CYS is a metabolite of acetaminophen (A161220) implicated in nephrotoxicity.

REFERENCES

• Huq, F., et al.: J. Pharmacol. Toxicol., 2, 142 (2007)
• Chen, C., et al.: J. Biol. Chem., 283, 4543 (2007)
• Reith, D., et al.: Clin. Exper. Pharmacol. Physiol., 36, 35 (2007)