(S)-3-{(2R,8S)-8-[(2S,5S,2'S,5'R)-5'-((5S,6S)-5,6-Dihydroxy-hexadecyl)-octahydro-[2,2']bifuranyl-5-yl]-2,8-dihydroxy-octyl}-5-methyl-5H-furan-2-one

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (S)-3-{(2R,8S)-8-[(2S,5S,2'S,5'R)-5'-((5S,6S)-5,6-Dihydroxy-hexadecyl)-octahydro-[2,2']bifuranyl-5-yl]-2,8-dihydroxy-octyl}-5-methyl-5H-furan-2-one
• 英文别名: (2S)-4-[(2R,8S)-8-[(2S,5S)-5-[(2S,5R)-5-[(5S,6S)-5,6-dihydroxyhexadecyl]oxolan-2-yl]oxolan-2-yl]-2,8-dihydroxyoctyl]-2-methyl-2H-furan-5-one
• 化学式: C₃₇H₆₆O₈
• 分子量: 638.926
• InChiKey: CXWUDOBKRFRXAX-JKRVFUSESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  45
• 可旋转键数：
  25
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  126
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  甲氧基-三氟甲基苯 、 (S)-3-{(2R,8S)-8-[(2S,5S,2'S,5'R)-5'-((5S,6S)-5,6-Dihydroxy-hexadecyl)-octahydro-[2,2']bifuranyl-5-yl]-2,8-dihydroxy-octyl}-5-methyl-5H-furan-2-one 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Glabracins A and B, two new acetogenins from Annona glabra

  摘要：

  Two new bioactive bis-THF Annonaceous acetogenins, glabracins A (1) and B (2), and two previously known acetogenins, javoricin (3) and bullatanocin (4), have been isolated from the leaves of Annona glabra by activity-directed fractionation using the brine shrimp lethality test (BST). The structures of 1 and 2 were elucidated based on spectroscopic and chemical methods, and the absolute stereochemistries were partially determined by the advanced Mosher ester method. 1 and 2 showed selective cytotoxicities to certain human tumor cell lines, and 1 was significantly more potent although 1 and 2 differ only in the stereochemistry of their vicinal diols at C-23/24. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(98)00059-5

文献信息

• Glabracins A and B, two new acetogenins from Annona glabra
  作者：Xiao-Xi Liu、Feras Q. Alali、D.Craig Hopp、Lingling L. Rogers、Elsa Pilarinou、Jerry L. McLaughlin

  DOI：10.1016/s0968-0896(98)00059-5

  日期：1998.7

  Two new bioactive bis-THF Annonaceous acetogenins, glabracins A (1) and B (2), and two previously known acetogenins, javoricin (3) and bullatanocin (4), have been isolated from the leaves of Annona glabra by activity-directed fractionation using the brine shrimp lethality test (BST). The structures of 1 and 2 were elucidated based on spectroscopic and chemical methods, and the absolute stereochemistries were partially determined by the advanced Mosher ester method. 1 and 2 showed selective cytotoxicities to certain human tumor cell lines, and 1 was significantly more potent although 1 and 2 differ only in the stereochemistry of their vicinal diols at C-23/24. (C) 1998 Elsevier Science Ltd. All rights reserved.