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

• ChemBase编号: 154810
• 分子式: C5H10N2O2S
• 平均质量: 162.2101
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: (2R)-2-acetamido-3-sulfanylpropanamide
• IUPAC传统名: (2R)-2-acetamido-3-sulfanylpropanamide
• 别名: (R)- 2-(Acetylamino)-3-mercapto-Propanamide; AD4; N-Acetyl-L-cysteinamide; NACA; acetylcysteinamide; N-acetylcysteine amide

登记号

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

理论计算性质

• Acid pKa: 9.961255
• 质子受体: 2
• 质子供体: 3
• LogD (pH = 5.5): -1.5182693
• LogD (pH = 7.4): -1.5193605
• Log P: -1.5182554
• 摩尔折射率: 39.4896 cm^3
• 极化性: 15.490339 Å^3
• 极化表面积: 72.19 Å^2
• 可自由旋转的化学键: 3
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: DMSO: >40 mg/mL; H2O: ≥20 mg/mL
• 外观: white to off-white powder

安全信息

• 保存条件: desiccated
• 欧盟危险性物质标志: 有害性(Harmful) (Xn)
• 德国WGK号: 3
• 危险公开号: 22
• GHS危险品标识: GHS07
• GHS警示词: Warning
• GHS危险声明: H302
• 保存温度: 2-8°C

产品相关信息

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

详细说明

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.