3-hydroxyimino-5β-cholan-24-oic acid | 106697-47-6

• 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: 3-hydroxyimino-5β-cholan-24-oic acid
• 英文别名: 3-oxo-5β-cholan-24-oic acid oxime；3-hydroxyimino-5β-cholanoic acid-(24)；3-Hydroxyimino-5β-cholansaeure-(24)
• CAS: 106697-47-6
• 化学式: C₂₄H₃₉NO₃
• 分子量: 389.579
• InChiKey: MUWLJZJGDNFZKF-OPTMKGCMSA-N

物化性质

• 沸点：
  539.9±23.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.98
• 重原子数：
  28.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  69.89
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  3-hydroxyimino-5β-cholan-24-oic acid 在 N-甲基吗啉 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 sodium hydroxide 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 N-(3-hydroxyimino-5β-cholan-24-oyl)-L-tryptophan
  参考文献：
  名称：

  Biochemical characterization of EphA2 antagonists with improved physico-chemical properties by cell-based assays and surface plasmon resonance analysis

  摘要：

  Amino acid conjugates of lithocholic acid (LCA) have been recently described as effective disruptors of the EphA2-ephrin-A1 interaction able to inhibit EphA2 phosphorylation in intact cells and thus able to block prometastatic responses such as cellular retraction and angiogenesis. However, these LCA-based compounds were significantly more potent at disrupting the EphA2-ephrin-A1 interaction than at blocking phenotype responses in cells, which might reflect an unclear mechanism of action or a metabolic issue responsible for a reduction of the compound concentration at the cell's surface. Through the synthesis of new compounds and their examination by a combination of cell -based assays and real-time interaction analysis by surface plasmon resonance, we showed at molecular level that L-tryptophan conjugates of lithocholic acid disrupt EphA2-ephrin-A1 interaction by targeting the EphA 2 receptor and that the presence of a polar group in position 3 of steroid scaffold is a key factor to increase the effective concentration of the compounds in cancer cell lines. (C) 2015 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bcp.2015.10.006
• 作为产物：
  描述：

  (5beta)-3-氧代-胆烷-24-酸 生成 3-hydroxyimino-5β-cholan-24-oic acid
  参考文献：
  名称：

  Redel et al., Bulletin de la Societe Chimique de France, 1949, p. 877,881

  摘要：

  DOI：

文献信息

• Bellini; Quaglio; Guarneri, Farmaco, Edizione Scientifica, 1986, vol. 41, # 5, p. 401 - 407
  作者：Bellini、Quaglio、Guarneri

  DOI：——

  日期：——
• Satoh; Hagitani, Nippon Kagaku Zasshi, 1959, vol. 80, p. 1310
  作者：Satoh、Hagitani

  DOI：——

  日期：——