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

• ChemBase编号: 133904
• 分子式: C24H47NO3
• 平均质量: 397.63488
• 单一同位素质量: 397.35559437
• SMILES: CCCCCCCCCCCCC/C=C/[C@H]([C@H](CO)NC(=O)CCCCC)O
• Canonical SMILES: CCCCCCCCCCCCC/C=C/[C@H]([C@@H](NC(=O)CCCCC)CO)O
• InChI: InChI=1S/C24H47NO3/c1-3-5-7-8-9-10-11-12-13-14-15-16-18-19-23(27)22(21-26)25-24(28)20-17-6-4-2/h18-19,22-23,26-27H,3-17,20-21H2,1-2H3,(H,25,28)/b19-18+/t22-,23+/m0/s1
• InChIKey: NPRJSFWNFTXXQC-QFWQFVLDSA-N

名称和登记号

名称

• IUPAC标准名: N-[(2S,3R,4E)-1,3-dihydroxyoctadec-4-en-2-yl]hexanamide
• IUPAC传统名: C6 ceramide
• 别名: N-[(1S,2R,3E)-2-Hydroxy-1-(hydroxymethyl)-3-heptadecen-1-yl]hexanamide; N-Hexanoy-D-sphingosine; N-Hexanoylsphingosine; C6 Ceramide; C6 ceramide; Caproyl ceramide; N-Caproyl-D-sphingosine; N-Hexanoyl-D-sphingosine

登记号

• CAS号: 124753-97-5
• MDL号: MFCD00870174
• PubChem SID: 24895750; 162228181
• PubChem CID: 5702613

理论计算性质

• Acid pKa: 13.63898
• 质子受体: 3
• 质子供体: 3
• LogD (pH = 5.5): 6.4196672
• LogD (pH = 7.4): 6.419668
• Log P: 6.4196687
• 摩尔折射率: 119.7657 cm^3
• 极化性: 47.144634 Å^3
• 极化表面积: 69.56 Å^2
• 可自由旋转的化学键: 20
• 里宾斯基五规则: false

分子性质

理化性质

• 溶解度: Chloroform; Methanol
• 外观: Off White Powder
• 熔点: 76-77°C

安全信息

• 保存条件: -20°C Freezer
• 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: from synthetic

详细说明

Sigma Aldrich - H6524

Biochem/physiol Actions
Cell-permeable analog of ceramide; stimulates protein phosphatase 2A; activates MAP kinase; induces apoptosis in human leukemia HL-60 cells

Toronto Research Chemicals - C262600

A biologically active, cell permeable, but nonphysiologic ceramide analog. It stimulates protein phosphatase 2A at concentrations as low as 10 nM and activiates MAP kinase. It induces apoptosis and inhibits glycoproptein traffic by the secretory pathway

参考文献

• Liu, Z., et al.: J. Neurochem., 106, 2463 (2008)
• Heakal, Y., et al.: Mol. Cancer Res., 7, 724 (2008)
• Chen-Quay, S., et al.: J. Pharm. Sci., 98, 606 (2008)
• Mahdy, A., et al.: Mol. Ther., 17, 430 (2008)