26,27-dinor-5β-cholestane-3α,7α,25-triol | 141099-43-6

• 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: 26,27-dinor-5β-cholestane-3α,7α,25-triol
• 英文别名: (3R,5S,7R,8R,9S,10S,13R,14S,17R)-17-[(2R)-6-hydroxyhexan-2-yl]-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3,7-diol
• CAS: 141099-43-6
• 化学式: C₂₅H₄₄O₃
• 分子量: 392.623
• InChiKey: HCNNMMOUHVMJSL-SHUSUIPQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.78
• 重原子数：
  28.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  60.69
• 氢给体数：
  3.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  (5R)-5-[(3R,5S,7R,8R,9S,10S,13R,14S,17R)-3,7-二羟基-10,13-二甲基-2,3,4,5,6,7,8,9,11,12,14,15,16,17-十四氢-1H-环戊二烯并[a]菲-17-基]己酸 在 lithium aluminium tetrahydride 作用下， 生成 26,27-dinor-5β-cholestane-3α,7α,25-triol
  参考文献：
  名称：

  Bile alcohols function as the ligands of membrane-type bile acid-activated G protein-coupled receptor

  摘要：

  TGR5 is a G protein-coupled receptor that is activated by bile acids, resulting in an increase in cAMP levels and the subsequent modulation of energy expenditure in brown adipose tissue and muscle. Therefore, the development of a TGR5-specific agonist could lead to the prevention and treatment of various metabolic disorders related to obesity. In the present study, we evaluated the ability of bile alcohols, which are structurally and physiologically similar to bile acids and are produced as the end products of cholesterol catabolism in evolutionarily primitive vertebrates, to act as TGR5 agonists. In a cell-based reporter assay and a cAMP production assay performed in vitro, most bile alcohols with a side chain containing hydroxyl group(s) were highly efficacious agonists for TGR5 comparable to its most potent ligand in the naturally occurring bile acid, lithocholic acid. However, the abilities of the bile alcohols to activate TGR5 varied with the position and number of the hydroxyl substituent in the side chain. Additionally, the conformation of the steroidal nucleus of bile alcohols is also important for its activity as a TGR5 agonist. Thus, we have provided new insights into the structure-activity relationships of bile alcohols as TGR5 agonists.-Iguchi, Y., M. Yamaguchi, H. Sato, K. Kihira, T. Nishimaki-Mogami, and M. Une. Bile alcohols function as the ligands of membrane-type bile acid-activated G protein-coupled receptor. J. Lipid Res. 2010. 51: 1432-1441.

  DOI：

  10.1194/jlr.m004051