2-acetamido-3-sulfanylpropanoic acid

• ChemBase ID: 125609
• Molecular Formular: C5H9NO3S
• Molecular Mass: 163.19486
• Monoisotopic Mass: 163.03031415
• SMILES: CC(=O)NC(CS)C(=O)O
• Canonical SMILES: SCC(C(=O)O)NC(=O)C
• InChI: InChI=1S/C5H9NO3S/c1-3(7)6-4(2-10)5(8)9/h4,10H,2H2,1H3,(H,6,7)(H,8,9)
• InChIKey: PWKSKIMOESPYIA-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-acetamido-3-sulfanylpropanoic acid
• IUPAC Traditional name: acetylcysteine
• Synonyms: Acetylcysteine

Database IDs

• CAS Number: 7218-04-4
• EC Number: 230-609-9
• Beilstein Number: 1724426 R
• PubChem SID: 162219959
• PubChem CID: 581
• CHEBI ID: 28939
• ATC CODE: S01XA08; R05CB01; V03AB23
• CHEMBL: 600
• Chemspider ID: 561
• DrugBank ID: DB06151
• Gmelin ID: 142554 R
• KEGG ID: D00221
• MeSH Name: Acetylcysteine
• Unique Ingredient Identifier: WYQ7N0BPYC
• Wikipedia Title: Acetylcysteine

CALCULATED PROPERTIES

• Acid pKa: 3.8175788
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): -2.396545
• LogD (pH = 7.4): -3.9664288
• Log P: -0.7113128
• Molar Refractivity: 37.6674 cm^3
• Polarizability: 14.845324 Å^3
• Polar Surface Area: 66.4 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: White, opaque crystals
• Melting Point: 106 - 108°C
• Partition Coefficient: -0.696
• pKa: 3.252
• pKb: 10.745

Safety Information

• RTECS: HA1660000 R
• Safety Statements: s22, s24/25
• LD50: 5.050 mg kg^-1 (oral, rat)

Pharmacology Properties

• Admin Routes: Inhalational; Intravenous; Oral
• Bioavailability: <3% (inhalational); 6–10% (oral)
• Excretion: Renal
• Half Life: 11 hours (neonates); 5.6 hours (adults)
• Metabolism: Hepatic
• Legal Status: Rx (US); Schedule 4 (Australia)
• Pregnancy Category: B (US); B2 (Australia)
• US Licence: ACETYLCYSTEINE