(3alpha,5beta,7alpha,8xi,12alpha)-7,12,24-三羟基-24-氧代胆烷-3-基beta-D-吡喃葡糖苷酸 | 76060-22-5

• 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
• 中文名称: (3alpha,5beta,7alpha,8xi,12alpha)-7,12,24-三羟基-24-氧代胆烷-3-基beta-D-吡喃葡糖苷酸
• 英文名称: 3α,7α,12α-trihydroxy-5β-cholan-24-oic acid 3-β-D-glucuronide
• 英文别名: Cholic acid glucuronide；(2S,3S,4S,5R,6R)-6-[[(3R,5R,7R,8R,9S,10S,12S,13R,14S,17R)-17-[(2R)-4-carboxybutan-2-yl]-7,12-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
• CAS: 76060-22-5
• 化学式: C₃₀H₄₈O₁₁
• 分子量: 584.705
• InChiKey: RBLDVEUUCHVWMW-SXYQVCRBSA-N

物化性质

• 沸点：
  794.5±60.0 °C(Predicted)
• 密度：
  1.38±0.1 g/cm3(Predicted)
• 物理描述：
  Solid

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  41
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  194
• 氢给体数：
  7
• 氢受体数：
  11

ADMET

代谢

胆酸葡萄糖苷酸是胆酸在人身体内已知的一种代谢物。

Cholic acid glucuronide is a known human metabolite of Cholic acid.

来源:NORMAN Suspect List Exchange

反应信息

• 作为产物：
  描述：

  benzyl cholate 在 水 、 sodium hydroxide 作用下， 以 甲苯 为溶剂， 20.0~38.0 ℃ 、689.49 kPa 条件下， 反应 1.0h， 生成 (3alpha,5beta,7alpha,8xi,12alpha)-7,12,24-三羟基-24-氧代胆烷-3-基beta-D-吡喃葡糖苷酸
  参考文献：
  名称：

  胆汁酸3-葡萄糖醛酸的合成，理化性质和生物活性：对胆汁酸信号传导和排毒的新见解

  摘要：

  葡萄糖醛酸化被认为是胆汁酸的重要排毒途径，尤其是在胆汁淤积的情况下。葡萄糖醛酸苷的毒性低于母体游离形式，并且更容易从尿液中排泄。然而，胆酸酸葡萄糖醛酸化的病理生理学意义仍在科学界引起争议和争论。由于缺乏制备生物学和药理学研究所需量的纯葡糖醛酸苷的适当方法，该领域的进展受到了极大的限制。在这项工作中，我们开发了胆汁酸C3-葡萄糖醛酸的新合成方法，从而可以方便地制备克级量。合成的化合物已根据理化性质和调节关键核受体（包括法尼醇X受体（FXR））的能力进行了表征。

  DOI：

  10.1016/j.ejmech.2017.12.034

文献信息

• COMPOSITIONS AND METHODS FOR TREATING OBESITY
  申请人：Atheronova Operations, Inc.

  公开号：EP2485738A2

  公开（公告）日：2012-08-15
• Lipodissolving dermatological topical preparation
  申请人：Zadini Filiberto

  公开号：US20070071706A1

  公开（公告）日：2007-03-29

  A dermatological topical preparation such as a cream, a lotion, an emulsion, a paste, an ointment and the likes where a lipo-dissolving emulsifier such as a biliary compound is transdermally delivered through the superficial layers of the skin into the subcutaneous adipose tissue with the use of skin permeability enhancers. Some of these skin permeability enhancers are cyclodextrins, while others are substances which have the peculiar property of enhancing delivery of the lipo-dissolving substance locally into the adipose subcutaneous tissue maximizing subcutaneous uptake while minimizing systemic absorption in order to achieve maximization of local effect.
• Dissolution of arterial cholesterol plaques by pharmacological preparation
  申请人：Zadini P. Filiberto

  公开号：US20070116754A1

  公开（公告）日：2007-05-24

  A pharmacological substance namely a biliary salt or acid or precursor or derivative with emulsifying properties administered into the systemic circulation of a patient via a variety of routes of administration including topical-mucous membrane such as sublingual, topical-dermatological such as via a skin patch, intravenous, subcutaneous, rectal, intramuscular, intradermal, inhalatory in form of inhaled microcrystals, intrarterial, systemic, or via specialized catheter for in loco delivery of the substance, said substance being capable of crossing the fibrous cap of the atherosclerotic plaque to reach and dissolving with its emulsifying properties the cholesterol aggregates and in general the lipidic core within the plaque. The solubilized cholesterol exits the plaque and enters finely dissolved into the systemic circulation leaving behind a plaque emptied of its lipid content: the plague appears as a virtual cavity roofed by the fibrous cap. As a result of this pharmacological action upon the atherosclerotic plaque by the compound, the plaque is no longer vulnerable to rupture and arterial flow is restituted to physiological pre-plaque formation values. This effect on the lipid core of the plaque is expected to reduce and/or eliminate altogether preexisting atherosclerotic lesions and significantly reduce chances of acute and chronic ischemic events.
• DISSOLUTION OF ARTERIAL PLAQUE
  申请人：ZADINI Filiberto

  公开号：US20080187569A1

  公开（公告）日：2008-08-07

  Embodiments of methods of treating atherosclerosis are described. In some embodiments an emulsifier is provided to achieve levels in the systemic circulation that are effective to solubilize atherosclerotic plaque, resulting in plaque regression. In some embodiments, levels of greater than 50 μM are achieved; in some embodiments levels ranging from about 100 μM to about 600 μM are achieved; in some embodiments, levels ranging from about 100 μM to about 300 μM are achieved. Emulsifiers can include bile salts, saponins, and ionic, nonionic, and zwitterionic detergents, or salts, conjugates, hydrates, solvates, or polymorphs thereof. In some embodiments, a statin can be administered simultaneously or sequentially with an emulsifier.
• Dissolution of Arterial Cholesterol Plaques by Pharmacologically Induced Elevation of Endogenous Bile Salts
  申请人：Zadini Filiberto P.

  公开号：US20080287429A1

  公开（公告）日：2008-11-20

  A group of pharmaceutical substances induce elevation of endogenous bile salts and acids via different mechanisms. The elevated circulating bile salts exert a beneficial effect in atherosclerosis by acting both as atherolytic and antiatherogenic agents. The result of the elevated circulating endogenous bile salt is the dissolution of cholesterol/lipidic aggregates of the atherosclerotic plaques.