[(2R,3R,4S,5R,6R)-3,4-dibenzoyloxy-6-[(1R,2S,4S,5'R,6R,7S,8R,9S,12S,13R,16S,18S,19S)-19-benzoyloxy-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2'-oxane]-16-yl]oxy-5-[(2S,3R,4R,5S,6S)-3,4,5-triacetyloxy-6-methyloxan-2-yl]oxyoxan-2-yl]methyl benzoate | 1173241-42-3

• 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: [(2R,3R,4S,5R,6R)-3,4-dibenzoyloxy-6-[(1R,2S,4S,5'R,6R,7S,8R,9S,12S,13R,16S,18S,19S)-19-benzoyloxy-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2'-oxane]-16-yl]oxy-5-[(2S,3R,4R,5S,6S)-3,4,5-triacetyloxy-6-methyloxan-2-yl]oxyoxan-2-yl]methyl benzoate
• CAS: 1173241-42-3
• 化学式: C₇₃H₈₆O₂₀
• 分子量: 1283.47
• InChiKey: OGVZSLWVODBXRH-YOZRCYPPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.6
• 重原子数：
  93
• 可旋转键数：
  23
• 环数：
  12.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  240
• 氢给体数：
  0
• 氢受体数：
  20

反应信息

• 作为反应物：
  描述：

  [(2R,3R,4S,5R,6R)-3,4-dibenzoyloxy-6-[(1R,2S,4S,5'R,6R,7S,8R,9S,12S,13R,16S,18S,19S)-19-benzoyloxy-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2'-oxane]-16-yl]oxy-5-[(2S,3R,4R,5S,6S)-3,4,5-triacetyloxy-6-methyloxan-2-yl]oxyoxan-2-yl]methyl benzoate 在 甲醇 、 sodium methylate 作用下， 生成 chlorogenin 3β-O-[2-O-(α-L-rhamnopyranosyl)-β-D-glucopyranoside]
  参考文献：
  名称：

  Discovery of the First Series of Small Molecule H5N1 Entry Inhibitors

  摘要：

  The occurrence of highly pathogenic avian influenza virus H5N1 highlights the urgent need for new classes of antiviral drugs. Inhibition of H5N1 entry into cells may be an effective strategy. We report the first three small molecule inhibitors saponins with 3-O-beta-chacotriosyl residue, which Showed potent inhibitory activity with IC50 of 7.22-9.25 mu M. The subsequent SAR studies showed the 3-O-beta-chacotriosyl residue was essential for the activity, and the aglycone structure also affected the activity.

  DOI：

  10.1021/jm900275m
• 作为产物：
  描述：

  6α-O-benzoyl chlorogenin 3β-O-(3,4,6-tri-O-benzoyl-β-D-glucopyranoside) 、 2,3,4-tri-O-acetyl-L-rhamnopyranosyl trichloroacetimidate 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 生成 [(2R,3R,4S,5R,6R)-3,4-dibenzoyloxy-6-[(1R,2S,4S,5'R,6R,7S,8R,9S,12S,13R,16S,18S,19S)-19-benzoyloxy-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2'-oxane]-16-yl]oxy-5-[(2S,3R,4R,5S,6S)-3,4,5-triacetyloxy-6-methyloxan-2-yl]oxyoxan-2-yl]methyl benzoate
  参考文献：
  名称：

  Discovery of the First Series of Small Molecule H5N1 Entry Inhibitors

  摘要：

  The occurrence of highly pathogenic avian influenza virus H5N1 highlights the urgent need for new classes of antiviral drugs. Inhibition of H5N1 entry into cells may be an effective strategy. We report the first three small molecule inhibitors saponins with 3-O-beta-chacotriosyl residue, which Showed potent inhibitory activity with IC50 of 7.22-9.25 mu M. The subsequent SAR studies showed the 3-O-beta-chacotriosyl residue was essential for the activity, and the aglycone structure also affected the activity.

  DOI：

  10.1021/jm900275m