kimbeamide A | 1373514-28-3

• 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: kimbeamide A
• 英文别名: (2E,4E,7E)-8-chloro-N-[(2S,3Z,7E)-8-chloroocta-3,7-dien-2-yl]-7-methylocta-2,4,7-trienamide
• CAS: 1373514-28-3
• 化学式: C₁₇H₂₃Cl₂NO
• 分子量: 328.282
• InChiKey: VOWNHWSVEUWZQX-HUVZLFSQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  21
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  kimbeamide A 在 双氧水 、 臭氧 、 盐酸 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 16.08h， 生成 L-丙氨酸
  参考文献：
  名称：

  Biosynthetically Intriguing Chlorinated Lipophilic Metabolites from Geographically Distant Tropical Marine Cyanobacteria

  摘要：

  Five new vinylchlorine-containing metabolites, the lipoamides janthielamide A and kimbeamides A-C and the ketide-extended pyranone kimbelactone A, have been isolated from collections of marine cyanobacteria made in Curacao and Papua New Guinea. Both janthielamide A and kimbeamide A exhibited moderate sodium channel blocking activity in murine Neuro-2a cells. Consistent with this activity, janthielamide A was also found to antagonize veratridine-induced sodium influx in murine cerebrocortical neurons. These lipoamides represent the newest additions to a relatively rare family of marine cyanobacterial-derived lipoamides and a new structural class of compounds exhibiting neuromodulatory activities from marine cyanobacteria.

  DOI：

  10.1021/jo300160e

文献信息

• Biosynthetically Intriguing Chlorinated Lipophilic Metabolites from Geographically Distant Tropical Marine Cyanobacteria
  作者：Joshawna K. Nunnery、Niclas Engene、Tara Byrum、Zhengyu Cao、Sairam V. Jabba、Alban R. Pereira、Teatulohi Matainaho、Thomas F. Murray、William H. Gerwick

  DOI：10.1021/jo300160e

  日期：2012.5.4

  Five new vinylchlorine-containing metabolites, the lipoamides janthielamide A and kimbeamides A-C and the ketide-extended pyranone kimbelactone A, have been isolated from collections of marine cyanobacteria made in Curacao and Papua New Guinea. Both janthielamide A and kimbeamide A exhibited moderate sodium channel blocking activity in murine Neuro-2a cells. Consistent with this activity, janthielamide A was also found to antagonize veratridine-induced sodium influx in murine cerebrocortical neurons. These lipoamides represent the newest additions to a relatively rare family of marine cyanobacterial-derived lipoamides and a new structural class of compounds exhibiting neuromodulatory activities from marine cyanobacteria.