N-[(2R,3R,4E)-1,3-dihydroxy(1,2-13C2,1,1-2H2)octadec-4-en-2-yl]hexanamide

• ChemBase编号: 163988
• 分子式: C24H47NO3
• 平均质量: 399.62018968
• 单一同位素质量: 399.36230405
• SMILES: CCCCCCCCCCCCC/C=C/[C@H]([13C@H]([13CH2]O)NC(=O)CCCCC)O
• Canonical SMILES: CCCCCCCCCCCCC/C=C/[C@H]([13C@@H](NC(=O)CCCCC)[13CH2]O)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/i21+1,22+1
• InChIKey: NPRJSFWNFTXXQC-OBHPOFNMSA-N

名称和登记号

名称

• IUPAC标准名: N-[(2R,3R,4E)-1,3-dihydroxy(1,2-^1^3C₂,1,1-^2H₂)octadec-4-en-2-yl]hexanamide
• IUPAC传统名: N-[(2R,3R,4E)-1,3-dihydroxy(1,2-^1^3C₂,1,1-^2H₂)octadec-4-en-2-yl]hexanamide
• 别名: N-Hexanoy-D-sphingosine-13C2,d2; N-Caproyl-D-sphingosine-13C2,d2; Caproyl Ceramide-13C2,d2; C6 Ceramide-13C2,d2

登记号

• PubChem SID: 162258123
• PubChem CID: 46780961

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 Solid
• 熔点: 69-72°C

安全信息

• 保存条件: -20°C Freezer

详细说明

Toronto Research Chemicals - C262602

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

• Dobrowsky, R.T., et al.: J. Biol. Chem., 268, 15523 (1993)
• Raines, M.A., et al.: J. Biol. Chem., 268, 14572 (1993)
• Jarvis, W.D., et al.: Proc. Natl. Acad. Sci. USA, 91, 73 (1993)