helleborogenone | 41059-91-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: helleborogenone
• 英文别名: Δ1,4-3-oxobufalin；14-Hydroxy-3-oxo-1,4,20,22-bufatetraenolide；5-[(8R,9S,10R,13R,14S,17R)-14-hydroxy-10,13-dimethyl-3-oxo-7,8,9,11,12,15,16,17-octahydro-6H-cyclopenta[a]phenanthren-17-yl]pyran-2-one
• CAS: 41059-91-0
• 化学式: C₂₄H₂₈O₄
• 分子量: 380.484
• InChiKey: YRBVLOVGZCCAQL-FIJLXMTKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  28
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  helleborogenone 在 sodium tetrahydroborate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 1.25h， 生成 海葱苷元
  参考文献：
  名称：

  Ribar, Bela; Argay, Gyula; Kalman, Alajos, Journal of Chemical Research, Miniprint, 1983, # 4, p. 1001 - 1042

  摘要：

  DOI：
• 作为产物：
  描述：

  海蟾蜍毒素 在 Comamonas testosteroni 作用下， 以 丙酮 为溶剂， 反应 96.0h， 生成 3-epimarinobufagin 、 3-oxomarinobufagin 、 helleborogenone 、 Δ^1,4-3-oxoresibufogenin
  参考文献：
  名称：

  Microbial biotransformation as a source of chemical diversity in cane toad steroid toxins

  摘要：

  The cane toad is an invasive pest that is rapidly colonising northern Australia. The cane toad parotoid gland secretes cardiotoxic steroids (bufadienolides) that are poisoning native predator species. This study reveals bufadienolide diversity within the secretions of Australian cane toads is different to cane toads from overseas, being far more structurally diverse than previously assumed. It is proposed that this variation is mediated by in situ bacterial biotransformation. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.01.064

文献信息

• Microbial biotransformation as a source of chemical diversity in cane toad steroid toxins
  作者：R. Andrew Hayes、Andrew M. Piggott、Kristian Dalle、Robert J. Capon

  DOI：10.1016/j.bmcl.2009.01.064

  日期：2009.3

  The cane toad is an invasive pest that is rapidly colonising northern Australia. The cane toad parotoid gland secretes cardiotoxic steroids (bufadienolides) that are poisoning native predator species. This study reveals bufadienolide diversity within the secretions of Australian cane toads is different to cane toads from overseas, being far more structurally diverse than previously assumed. It is proposed that this variation is mediated by in situ bacterial biotransformation. (C) 2009 Elsevier Ltd. All rights reserved.
• Ribar, Bela; Argay, Gyula; Kalman, Alajos, Journal of Chemical Research, Miniprint, 1983, # 4, p. 1001 - 1042
  作者：Ribar, Bela、Argay, Gyula、Kalman, Alajos、Vladimirov, Sote、Zivanov-Stakic, Dobrila

  DOI：——

  日期：——