[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-17-[(2R)-5-[3-[[(4R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-10,13-dimethyl-3,7,12-trisulfooxy-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoyl]amino]propyl-[4-[[(4R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-10,13-dimethyl-3,7,12-trisulfooxy-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoyl]-[3-[[(4R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-10,13-dimethyl-3,7,12-trisulfooxy-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoyl]amino]propyl]amino]butyl]amino]-5-oxopentan-2-yl]-10,13-dimethyl-3,7-disulfooxy-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-12-yl] hydrogen sulfate

• 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: [(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-17-[(2R)-5-[3-[[(4R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-10,13-dimethyl-3,7,12-trisulfooxy-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoyl]amino]propyl-[4-[[(4R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-10,13-dimethyl-3,7,12-trisulfooxy-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoyl]-[3-[[(4R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-10,13-dimethyl-3,7,12-trisulfooxy-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoyl]amino]propyl]amino]butyl]amino]-5-oxopentan-2-yl]-10,13-dimethyl-3,7-disulfooxy-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-12-yl] hydrogen sulfate
• 化学式: C₁₀₆H₁₇₈N₄O₅₂S₁₂
• 分子量: 2725.37
• InChiKey: NNGIFGBQYFYOGV-IOVFAINRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.8
• 重原子数：
  174
• 可旋转键数：
  53
• 环数：
  16.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  963
• 氢给体数：
  14
• 氢受体数：
  52

反应信息

• 作为产物：
  描述：

  N₁,N₂,N₃,N₄-spermine-tetracholeamide 在 pyridine-SO3 complex 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 [(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-17-[(2R)-5-[3-[[(4R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-10,13-dimethyl-3,7,12-trisulfooxy-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoyl]amino]propyl-[4-[[(4R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-10,13-dimethyl-3,7,12-trisulfooxy-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoyl]-[3-[[(4R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-10,13-dimethyl-3,7,12-trisulfooxy-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoyl]amino]propyl]amino]butyl]amino]-5-oxopentan-2-yl]-10,13-dimethyl-3,7-disulfooxy-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-12-yl] hydrogen sulfate
  参考文献：
  名称：

  过硫酸化分子伞作为抗 HIV 和抗 HSV 药物

  摘要：

  已经从腐胺、亚精胺、精胺、赖氨酸和胆酸（1a、2a、3a、4a 和 5a）合成了一系列过硫酸化分子伞，并确定了它们的抗 HIV 和抗 HSV 活性。尽管大小，这些缀合物中最活跃的 (5a) 能够穿过由 1-棕榈酰-2-油酰-sn-甘油-3-磷酸胆碱 (POPC) 和 1-棕榈酰-2-油酰-sn-制成的磷脂双层甘油-3-磷脂酰甘油 (POPG)。抗病毒活性、跨越疏水屏障的能力、缺乏细胞毒性以及从生物起始材料的简单三步合成的独特组合表明 5a 和相关缀合物可用作一类新型抗病毒剂用于全身和局部应用。

  DOI：

  10.1021/ja044400o

文献信息

• Persulfated Molecular Umbrellas as Anti-HIV and Anti-HSV Agents
  作者：Bingwen Jing、Vaclav Janout、Betsy C. Herold、Mary E. Klotman、Taylor Heald、Steven L. Regen

  DOI：10.1021/ja044400o

  日期：2004.12.1

  A series of persulfated molecular umbrellas have been synthesized from putrescine, spermidine, spermine, lysine, and cholic acid (1a, 2a, 3a, 4a, and 5a) and their anti-HIV and anti-HSV activities determined. Despite it size, the most active of these conjugates (5a) was able to cross phospholipid bilayers made from 1-palmitoyl-2-oleyol-sn-glycero-3-phosphocholine (POPC) and 1-palmitoyl-2-oleoyl-sn

  已经从腐胺、亚精胺、精胺、赖氨酸和胆酸（1a、2a、3a、4a 和 5a）合成了一系列过硫酸化分子伞，并确定了它们的抗 HIV 和抗 HSV 活性。尽管大小，这些缀合物中最活跃的 (5a) 能够穿过由 1-棕榈酰-2-油酰-sn-甘油-3-磷酸胆碱 (POPC) 和 1-棕榈酰-2-油酰-sn-制成的磷脂双层甘油-3-磷脂酰甘油 (POPG)。抗病毒活性、跨越疏水屏障的能力、缺乏细胞毒性以及从生物起始材料的简单三步合成的独特组合表明 5a 和相关缀合物可用作一类新型抗病毒剂用于全身和局部应用。