(2R)-2-acetamido-3-sulfanylpropanamide

• ChemBase ID: 154810
• Molecular Formular: C5H10N2O2S
• Molecular Mass: 162.2101
• Monoisotopic Mass: 162.04629857
• SMILES: CC(=O)N[C@@H](CS)C(=O)N
• Canonical SMILES: SC[C@@H](C(=O)N)NC(=O)C
• InChI: InChI=1S/C5H10N2O2S/c1-3(8)7-4(2-10)5(6)9/h4,10H,2H2,1H3,(H2,6,9)(H,7,8)/t4-/m0/s1
• InChIKey: UJCHIZDEQZMODR-BYPYZUCNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-2-acetamido-3-sulfanylpropanamide
• IUPAC Traditional name: (2R)-2-acetamido-3-sulfanylpropanamide
• Synonyms: (R)- 2-(Acetylamino)-3-mercapto-Propanamide; AD4; N-Acetyl-L-cysteinamide; NACA; acetylcysteinamide; N-acetylcysteine amide

Database IDs

• CAS Number: 38520-57-9
• MDL Number: MFCD01696115
• PubChem SID: 162248948
• PubChem CID: 10176265

CALCULATED PROPERTIES

• Acid pKa: 9.961255
• H Acceptors: 2
• H Donor: 3
• LogD (pH = 5.5): -1.5182693
• LogD (pH = 7.4): -1.5193605
• Log P: -1.5182554
• Molar Refractivity: 39.4896 cm^3
• Polarizability: 15.490339 Å^3
• Polar Surface Area: 72.19 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: >40 mg/mL; H2O: ≥20 mg/mL
• Apperance: white to off-white powder

Safety Information

• Storage Condition: desiccated
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C5H10N2O2S

DETAILS

Sigma Aldrich - A0737

Other Notes
This product is hydroscopic and air sensitive.
Biochem/physiol Actions
N-acetylcysteine amide is a membrane penetrating antioxidant with antiinflamatory activity through regulation of activation of NF-κB and HIF-1α as well as modulation of ROS. The compound readily crosses cell membranes, replenishes intracellular GSH, and defends the cell from oxidative stress. In contrast to DTT, AD4 is able to directly reduce intracellularl GSSG to GSH without the involvement of glutathione peroxidase. Such direct thiol exchange might have a protective effect. This compound has a potential in research and exploration for treatment of neurodegeneration, radiation exposure, and other oxidation-mediated disorders.