N-[(2R,3S,4E)-1,3-dihydroxyoctadec-4-en-2-yl]acetamide

• ChemBase编号: 133129
• 分子式: C20H39NO3
• 平均质量: 341.52856
• 单一同位素质量: 341.29299411
• SMILES: CCCCCCCCCCCCC/C=C/[C@@H]([C@@H](CO)NC(=O)C)O
• Canonical SMILES: CCCCCCCCCCCCC/C=C/[C@@H]([C@H](NC(=O)C)CO)O
• InChI: InChI=1S/C20H39NO3/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-20(24)19(17-22)21-18(2)23/h15-16,19-20,22,24H,3-14,17H2,1-2H3,(H,21,23)/b16-15+/t19-,20+/m1/s1
• InChIKey: BLTCBVOJNNKFKC-HEQKZDDYSA-N

名称和登记号

名称

• IUPAC标准名: N-[(2R,3S,4E)-1,3-dihydroxyoctadec-4-en-2-yl]acetamide
• IUPAC传统名: N-[(2R,3S,4E)-1,3-dihydroxyoctadec-4-en-2-yl]acetamide
• 别名: (2S,3R,4E)-2-(Acetylamino)-4-octadecene-1,3-diol; N-Acetoyl-D-erythro-sphingosine; Acetyl ceramide; C2 Ceramide (d18:1/2:0); C2 ceramide; N-Acetyl-D-sphingosine

登记号

• CAS号: 3102-57-6
• MDL号: MFCD00153903
• PubChem SID: 162227406; 24891187
• PubChem CID: 10427441

理论计算性质

• Acid pKa: 13.590839
• 质子受体: 3
• 质子供体: 3
• LogD (pH = 5.5): 4.3854265
• LogD (pH = 7.4): 4.3854265
• Log P: 4.3854265
• 摩尔折射率: 101.3358 cm^3
• 极化性: 39.77093 Å^3
• 极化表面积: 69.56 Å^2
• 可自由旋转的化学键: 16
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: DMSO: soluble; ethanol: soluble
• 外观: white powder

安全信息

• 德国WGK号: 3
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• 保存温度: -20°C

产品相关信息

• 纯度: ~98% (TLC)
• 生物来源: semisynthetic

详细说明

Sigma Aldrich - A7191

Biochem/physiol Actions
Cell-permeable, biologically active ceramide. It induces differentiation and apoptosis in cells and has been shown to activate protein phosphatases.
Preparation Note
Prepared from D-sphingosine from bovine brain cerebrosides.
Application
N-Acetyl-D-sphingosine is a cell-permeable and biologically active ceramide. N-Acetyl-D-sphingosine induces differentiation and apoptosis in cells. N-Acetyl-D-sphingosine produces concentration-dependent impairment of vasorelaxation in response to the endothelium-dependent agonist acetylcholine in nontransgenic mice.