3b-O-Glutaryl-18-b-glycyrrhetinic acid | 52048-37-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 3b-O-Glutaryl-18-b-glycyrrhetinic acid
• 英文别名: (3I(2),20I(2))-3-(4-Carboxy-1-oxobutoxy)-11-oxoolean-12-en-29-oic acid；(2S,4aS,6aR,6aS,6bR,8aR,10S,12aS,14bR)-10-(4-carboxybutanoyloxy)-2,4a,6a,6b,9,9,12a-heptamethyl-13-oxo-3,4,5,6,6a,7,8,8a,10,11,12,14b-dodecahydro-1H-picene-2-carboxylic acid
• CAS: 52048-37-0
• 化学式: C₃₅H₅₂O₇
• 分子量: 584.794
• InChiKey: ZTNPXVGUEPZDFZ-BMJPTYCDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  42
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  118
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  甘草次酸 、 5,5'-氧双(5-氧代戊酸) 在 吡啶 、 4-二甲氨基吡啶 作用下， 生成 3b-O-Glutaryl-18-b-glycyrrhetinic acid
  参考文献：
  名称：

  Synthesis and proteasome inhibition of glycyrrhetinic acid derivatives

  摘要：

  This study discovered that glycyrrhetinic acid inhibited the human 20S proteasome at 22.3 mu M. Esterification of the C-3 hydroxyl group on glycyrrhetinic acid with various carboxylic acid reagents yielded a series of analogs with marked improved potency. Among the derivatives, glycyrrhetinic acid 3-O-isophthalate (17) was the most potent compound with IC50 of 0.22 mu M, which was approximately 100-fold more potent than glycyrrhetinic acid. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.05.078