N-[(1S,2R)-2-hydroxy-1-(hydroxymethyl)tetradecyl]-5-methyl-3-(2-methyl-propyl)hexanamide | 1142922-78-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: N-[(1S,2R)-2-hydroxy-1-(hydroxymethyl)tetradecyl]-5-methyl-3-(2-methyl-propyl)hexanamide
• 英文别名: N-[(2S,3R)-1,3-dihydroxypentadecan-2-yl]-5-methyl-3-(2-methylpropyl)hexanamide
• CAS: 1142922-78-8
• 化学式: C₂₆H₅₃NO₃
• 分子量: 427.712
• InChiKey: ULRKIQBHNAYAMB-LOSJGSFVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.4
• 重原子数：
  30
• 可旋转键数：
  20
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  69.6
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N-[(3E)(1S,2R)-2-hydroxy-1-(hydroxymethyl)tetradec-3-enyl]-5-methyl-3-(2-methylpropyl)hexanamide 在 5%-palladium/activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 0.5h， 生成 N-[(1S,2R)-2-hydroxy-1-(hydroxymethyl)tetradecyl]-5-methyl-3-(2-methyl-propyl)hexanamide
  参考文献：
  名称：

  Ceramides: Branched alkyl chains in the sphingolipid siblings of diacylglycerol improve biological potency

  摘要：

  The synthesis of a small number of ceramide analogues containing a combination of linear and highly branched alkyl chains on either the D-sphingosine or the N-acyl core of the molecule is reported. Regardless of location, the presence of the branched chain improves potency relative to the positive control, C2 ceramide; however, the most potent compound (4) has the branched side chain as part of the D-sphingosine core. The induction of apoptosis by 4 in terms of Annexin V binding and DiOC(6) labeling was superior to that achieved with C2 ceramide. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.01.005

文献信息

• Ceramides: Branched alkyl chains in the sphingolipid siblings of diacylglycerol improve biological potency
  作者：Ji-Hye Kang、Himanshu Garg、Dina M. Sigano、Nicholas Francella、Robert Blumenthal、Victor E. Marquez

  DOI：10.1016/j.bmc.2009.01.005

  日期：2009.2

  The synthesis of a small number of ceramide analogues containing a combination of linear and highly branched alkyl chains on either the D-sphingosine or the N-acyl core of the molecule is reported. Regardless of location, the presence of the branched chain improves potency relative to the positive control, C2 ceramide; however, the most potent compound (4) has the branched side chain as part of the D-sphingosine core. The induction of apoptosis by 4 in terms of Annexin V binding and DiOC(6) labeling was superior to that achieved with C2 ceramide. (c) 2009 Elsevier Ltd. All rights reserved.