((1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-3a-Hydroxymethyl-1-isopropenyl-5a,5b,8,8,11a-pentamethyl-icosahydro-cyclopenta[a]chrysen-9-yloxycarbonylmethoxy)-acetic acid

• 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: ((1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-3a-Hydroxymethyl-1-isopropenyl-5a,5b,8,8,11a-pentamethyl-icosahydro-cyclopenta[a]chrysen-9-yloxycarbonylmethoxy)-acetic acid
• 英文别名: 2-[2-[[(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-3a-(hydroxymethyl)-1-isopropenyl-5a,5b,8,8,11a-pentamethyl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysen-9-yl]oxy]-2-oxo-ethoxy]acetic acid；2-[2-[[(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-3a-(hydroxymethyl)-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysen-9-yl]oxy]-2-oxoethoxy]acetic acid
• 化学式: C₃₄H₅₄O₆
• 分子量: 558.799
• InChiKey: DZQCMEUZSIANSF-QOMFFSOSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.3
• 重原子数：
  40
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  93.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  白桦脂醇 在 吡啶 、 4-二甲氨基吡啶 、 4-甲基苯磺酸吡啶 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 ((1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-3a-Hydroxymethyl-1-isopropenyl-5a,5b,8,8,11a-pentamethyl-icosahydro-cyclopenta[a]chrysen-9-yloxycarbonylmethoxy)-acetic acid
  参考文献：
  名称：

  3-O-Glutaryl-dihydrobetulin and related monoacyl derivatives as potent anti-HIV agents

  摘要：

  3-O-Acyl-betulin and -dihydrobetulin derivatives were prepared and evaluated for anti-HIV activity. 3-O-Glutaryl-dihydrobetulin (17) demonstrated extremely potent anti-HIV activity with an EC50 value of 2 x 10(-5) muM and a TI value of 1.12 x 10(6). 3-O-(3',3'-Dimethylsuccinyl)- and 3-O-(3',3'-dimethylglutaryl)-dihydrobetulins (15, 16) were also potent anti-HIV compounds with EC50 values of 0.0017 and 0.0013 muM, respectively, and TI values of 16,160 and 19,530, respectively. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.09.033

文献信息

• 3-O-Glutaryl-dihydrobetulin and related monoacyl derivatives as potent anti-HIV agents
  作者：Yoshiki Kashiwada、Michiko Sekiya、Yasumasa Ikeshiro、Toshihiro Fujioka、Nicole R. Kilgore、Carl T. Wild、Graham P. Allaway、Kuo-Hsiung Lee

  DOI：10.1016/j.bmcl.2004.09.033

  日期：2004.12

  3-O-Acyl-betulin and -dihydrobetulin derivatives were prepared and evaluated for anti-HIV activity. 3-O-Glutaryl-dihydrobetulin (17) demonstrated extremely potent anti-HIV activity with an EC50 value of 2 x 10(-5) muM and a TI value of 1.12 x 10(6). 3-O-(3',3'-Dimethylsuccinyl)- and 3-O-(3',3'-dimethylglutaryl)-dihydrobetulins (15, 16) were also potent anti-HIV compounds with EC50 values of 0.0017 and 0.0013 muM, respectively, and TI values of 16,160 and 19,530, respectively. (C) 2004 Elsevier Ltd. All rights reserved.