shikometabolin E

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 英文名称: shikometabolin E
• 英文别名: 6-[1,4-dihydroxy-3-[(1E)-4-methylpenta-1,3-dienyl]-5,8-dioxo-6,7-dihydronaphthalen-2-yl]-5,8-dihydroxy-7-(4-methylpent-3-enyl)-2,3-dihydronaphthalene-1,4-dione
• 化学式: C₃₂H₃₂O₈
• 分子量: 544.601
• InChiKey: WXAVWKRSKYMNCE-WEVVVXLNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  40
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  149
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  紫草素 以 二甲基亚砜 为溶剂， 反应 72.0h， 以0.76%的产率得到metaboshikonin I
  参考文献：
  名称：

  Biotransformation of shikonin by human intestinal bacteria

  摘要：

  The bacterial transformation of shikonin (1) in culture media has been investigated using human intestinal bacteria. Of 24 anaerobes tested, Bacteroides fragilis subsp. thetaotus showed an ability to transform 1 extensively to ten metabolites, five monomers; anhydroalkannin (2), deoxyshikonin (3), cycloshikonin (4), metaboshikonin I (5) and II (6), and five dimers; shikometabolins A (7), B (8), C (9), D (10) and E (11), after anaerobic incubation for 3 days. The structures of these metabolites were determined mainly by 2D-NMR including the INADEQUATE experiment.

  DOI：

  10.1016/s0040-4020(01)81108-x