2-(5α,6β-dihydroxycholestan-3β-yl)-acetic acid | 1620077-94-2

• 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: 2-(5α,6β-dihydroxycholestan-3β-yl)-acetic acid
• 英文别名: 2-[[(3S,5R,6R,8S,9S,10R,13R,14S,17R)-5,6-dihydroxy-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-1,2,3,4,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-yl]oxy]acetic acid
• CAS: 1620077-94-2
• 化学式: C₂₉H₅₀O₅
• 分子量: 478.713
• InChiKey: ONJBNHBGTZVQQU-YMNQVYQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  34
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  87
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(5α,6β-dihydroxycholestan-3β-yl)-acetic acid 在 4-二甲氨基吡啶 、 四丁基氟化铵 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 2-[[(3S,5R,6R,8S,9S,10R,13R,14S,17R)-5,6-dihydroxy-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-1,2,3,4,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-yl]oxy]-N,N-bis(2-hydroxyethyl)acetamide
  参考文献：
  名称：

  Structure–activity relationships of oxysterol-derived pharmacological chaperones for Niemann–Pick type C1 protein

  摘要：

  Niemann-Pick disease type C is a fatal neurodegenerative disease, and its major cause is mutations in NPC1 gene. This gene encodes NPC1 protein, a late endosomal polytopic membrane protein required for intracellular cholesterol trafficking. One prevalent mutation (11061T) has been shown to cause a folding defect, which results in failure of endosomal localization of the protein, leading to loss-of-function phenotype. We have previously demonstrated that several oxysterols and their derivatives act as pharmacological chaperones; binding of these compounds to NPC1(11061T) mutant protein corrects the localization/maturation defect of the mutant protein. Here, we disclose detailed structure-activity relationships of oxysterol derivatives as pharmacological chaperones for NPC1(11061T) mutant. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.05.064
• 作为产物：
  描述：

  mo56HC 在 水 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 6.0h， 以90%的产率得到2-(5α,6β-dihydroxycholestan-3β-yl)-acetic acid
  参考文献：
  名称：

  Structure–activity relationships of oxysterol-derived pharmacological chaperones for Niemann–Pick type C1 protein

  摘要：

  Niemann-Pick disease type C is a fatal neurodegenerative disease, and its major cause is mutations in NPC1 gene. This gene encodes NPC1 protein, a late endosomal polytopic membrane protein required for intracellular cholesterol trafficking. One prevalent mutation (11061T) has been shown to cause a folding defect, which results in failure of endosomal localization of the protein, leading to loss-of-function phenotype. We have previously demonstrated that several oxysterols and their derivatives act as pharmacological chaperones; binding of these compounds to NPC1(11061T) mutant protein corrects the localization/maturation defect of the mutant protein. Here, we disclose detailed structure-activity relationships of oxysterol derivatives as pharmacological chaperones for NPC1(11061T) mutant. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.05.064