suvanine | 112576-08-6

• 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: suvanine
• 英文别名: Suvanine'S sodium salt；sodium;[(E)-[(1R,4aR,4bS,8aS,10aS)-1-[2-(furan-3-yl)ethyl]-4b,8,8,10a-tetramethyl-1,3,4,4a,5,6,7,8a,9,10-decahydrophenanthren-2-ylidene]methyl] sulfate
• CAS: 112576-08-6
• 化学式: C₂₅H₃₇O₅S*Na
• 分子量: 472.622
• InChiKey: LCLILMARVYROOR-VNINRLMRSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  3.24
• 重原子数：
  32
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  88
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  suvanine 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 反应 48.5h， 生成 Sulfuric acid mono-[(1R,4aR,4bS,8aS,10aS)-4b,8,8,10a-tetramethyl-1-[2-(tetrahydro-furan-3-yl)-ethyl]-dodecahydro-phenanthren-(2E)-ylidenemethyl] ester; compound with N,N-dimethyl-guanidine
  参考文献：
  名称：

  Chemistry and revised structure of suvanine

  摘要：

  DOI：

  10.1021/jo00238a017

文献信息

• Binding Mechanism of the Farnesoid X Receptor Marine Antagonist Suvanine Reveals a Strategy To Forestall Drug Modulation on Nuclear Receptors. Design, Synthesis, and Biological Evaluation of Novel Ligands
  作者：Francesco Saverio Di Leva、Carmen Festa、Claudio D’Amore、Simona De Marino、Barbara Renga、Maria Valeria D’Auria、Ettore Novellino、Vittorio Limongelli、Angela Zampella、Stefano Fiorucci

  DOI：10.1021/jm400419e

  日期：2013.6.13

  Here, we report suvanine, a marine sponge sesterterpene, as an antagonist of the mammalian bile acid sensor farnesoid-X-receptor (FXR). Using suvanine as a template, we shed light on the molecular bases of FXR antagonism, identifying the essential conformational changes responsible for the transition from the agonist to the antagonist form. Molecular characterization of the nuclear corepressor NCoR and coactivator Src-1 revealed that receptor conformational changes are associated with a specific dynamic of recruitment of these cofactors to the promoter of OST alpha, a FXR regulated gene. Using suvanine as a novel hit, a library of semisynthetic derivatives has been designed and prepared, leading to pharmacological profiles ranging from agonism to antagonism toward FXR. Deep pharmacological evaluation demonstrated that derivative 19 represents a new chemotype of FXR modulator, whereas alcohol 6, with a simplified molecular scaffold, exhibits excellent antagonistic activity.
• Chemistry and revised structure of suvanine
  作者：Lawrence V. Manes、Phillip Crews、Michael R. Kernan、D. John Faulkner、Frank R. Fronczek、Richard D. Gandour

  DOI：10.1021/jo00238a017

  日期：1988.2