(2R,5S,8S,11S,15S)-8-benzyl-15-carboxy-5-(3-(iminio(3-methylureido)methylamino)propyl)-7-methyl-2-(2-(methylthio)ethyl)-3,6,9,13,17-pentaoxo-1,4,7,10,14-pentaazacycloheptadecane-11-carboxylate | 1166820-56-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2R,5S,8S,11S,15S)-8-benzyl-15-carboxy-5-(3-(iminio(3-methylureido)methylamino)propyl)-7-methyl-2-(2-(methylthio)ethyl)-3,6,9,13,17-pentaoxo-1,4,7,10,14-pentaazacycloheptadecane-11-carboxylate
• 英文别名: (2R,5S,8S,11S,15S)-5-[3-[[amino-(methylcarbamoylamino)methylidene]amino]propyl]-8-benzyl-7-methyl-2-(2-methylsulfanylethyl)-3,6,9,13,17-pentaoxo-1,4,7,10,14-pentazacycloheptadecane-11,15-dicarboxylic acid
• CAS: 1166820-56-9
• 化学式: C₃₁H₄₅N₉O₁₀S
• 分子量: 735.819
• InChiKey: VPNNDGQKIBPNIZ-FXTUREPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  51
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  316
• 氢给体数：
  9
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  (2R,5S,8S,11S,15S)-8-benzyl-15-(4-benzylpiperidine-1-carbonyl)-5-(3-(iminio(3-methylureido)methylamino)propyl)-2-isobutyl-7-methyl-3,6,9,13,17-pentaoxo-1,4,7,10,14-pentaazacycloheptadecane-11-carboxylate 在 三氟乙酸 作用下， 生成 (2R,5S,8S,11S,15S)-8-benzyl-15-carboxy-5-(3-(iminio(3-methylureido)methylamino)propyl)-7-methyl-2-(2-(methylthio)ethyl)-3,6,9,13,17-pentaoxo-1,4,7,10,14-pentaazacycloheptadecane-11-carboxylate
  参考文献：
  名称：

  Computer-aided rational molecular design of argifin-derivatives with increased inhibitory activity against chitinase B from Serratia marcescens

  摘要：

  Argifin, a novel pentapeptide chitinase inhibitor isolated from Gliocladium fungal culture, is a promising candidate for the development of new fungicides, insecticides, and anti-asthma medications. In this study, we undertook rational molecular design of argifin-derivatives and tested them against chitinase B from Serratia marcescens (SmChiB). The work involved molecular dynamics simulation with explicit water molecules, the molecular docking calculation, and free-energy analysis using the molecular mechanics Poisson-Boltzmann surface area method. The custom-designed derivatives were synthesized via effective solid phase synthesis, developed recently in our laboratory, and their inhibitory activities were measured against SmChiB. Finally, we identified and obtained a derivative which exhibited 28-fold more inhibition than argifin itself, a compound in which the D-Ala(5) of argifin was replaced with D-Leu and the 4-benzylpiperdine was attached to L-Asp(4). (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.04.013