penasin D | 1254939-51-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧唑烯
• 英文名称: penasin D
• 英文别名: (2S,3S,4S)-4-amino-2-[(Z)-16-methyltetracos-7-enyl]oxolan-3-ol
• CAS: 1254939-51-9
• 化学式: C₂₉H₅₇NO₂
• 分子量: 451.777
• InChiKey: BACNCVMSOBUKPQ-VUDYHDPXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.4
• 重原子数：
  32
• 可旋转键数：
  22
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  55.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  penasin C 、 penasin D 、 penasin E 在 臭氧 、 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 0.16h， 生成 8-methyl-heptadecan-1-ol 、 10-methyl-heptadecan-1-ol 、 9-Methylheptadecan-1-ol
  参考文献：
  名称：

  Penasins A−E, Long-Chain Cytotoxic Sphingoid Bases, from a Marine Sponge Penares sp

  摘要：

  Five sphingoid bases, penasin A (1), penasin B (2), and a mixture of penasins C-E (3-5), were identified from a marine sponge Penares sp. as cytotoxic constituents. The structure of the common polar head part was assigned by analysis of the NMR data, whereas the structures of the long aliphatic chains including the locations of double bond(s) and a branched methyl group were determined by analysis of tandem FABMS and C-13 NMR data together with the GC-MS analysis of ozonolysis products. The absolute configuration of the headgroup was defined for the mixture of 3-5 by the modified Mosher method. Penasins exhibit moderate cytotoxicity against HeLa and P388 cells.

  DOI：

  10.1021/np1003565