(2Z,4E)-5-((1S,2R,6R)-2-Hydroxy-1,3-dimethyl-5-oxo-bicyclo[4.1.0]hept-3-en-2-yl)-3-methyl-penta-2,4-dienoic acid | 179239-69-1

• 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: (2Z,4E)-5-((1S,2R,6R)-2-Hydroxy-1,3-dimethyl-5-oxo-bicyclo[4.1.0]hept-3-en-2-yl)-3-methyl-penta-2,4-dienoic acid
• 英文别名: CycloABA；(2Z,4E)-5-[(1S,2R,6R)-2-hydroxy-1,3-dimethyl-5-oxo-2-bicyclo[4.1.0]hept-3-enyl]-3-methylpenta-2,4-dienoic acid
• CAS: 179239-69-1
• 化学式: C₁₅H₁₈O₄
• 分子量: 262.306
• InChiKey: HFWFLWSKSVJXJC-AZZUMJRSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2Z,4E)-5-((1S,2R,6R)-2-Hydroxy-1,3-dimethyl-5-oxo-bicyclo[4.1.0]hept-3-en-2-yl)-3-methyl-penta-2,4-dienoic acid 、 2,3,4,6-四乙酰氧基-alpha-D-吡喃葡萄糖溴化物 在 silver carbonate 作用下， 以 乙醚 为溶剂， 反应 5.0h， 以4%的产率得到(2Z,4E)-5-((1S,2R,6R)-2-Hydroxy-1,3-dimethyl-5-oxo-bicyclo[4.1.0]hept-3-en-2-yl)-3-methyl-penta-2,4-dienoic acid (2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yl ester
  参考文献：
  名称：

  Metabolism of 5′α,8′-cycloabscisic acid, a highly potent and long-lasting abscisic acid analogue, in radish seedlings

  摘要：

  We synthesized 5'alpha,8'-cycloabscisic acid (CycloABA), a highly potent and long-lasting abscisic acid (ABA) analogue, by a different method from that reported before. CycloABA fed to radish seedlings had more metabolic tolerance than ABA. The major metabolite of CycloABA was the glucose conjugate, which was the minor metabolite of ABA. The 8'-hydroxylated metabolite and its cyclized isomer, which were major metabolites of ABA, were not found as metabolites of CycloABA. The present results suggest that the highly potent and long-lasting activity of CycloABA is caused by resistance to ABA 8'-hydroxylase, and that CycloABA is partially metabolized to the glucose conjugate by ABA glucosyltransferase. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2003.10.048
• 作为产物：
  描述：

  4,6-dimethyl-5H-spiro-[bicyclo[4.1.0]hept-3-ene-2,2'-[1,3]dioxolane]-5-one 在 manganese(IV) oxide 、 sodium hydroxide 、 正丁基锂 、 双(三甲基硅烷基)氨基钾 、 红铝 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 甲苯 为溶剂， 反应 55.0h， 生成 (2Z,4E)-5-((1S,2R,6R)-2-Hydroxy-1,3-dimethyl-5-oxo-bicyclo[4.1.0]hept-3-en-2-yl)-3-methyl-penta-2,4-dienoic acid
  参考文献：
  名称：

  Metabolism of 5′α,8′-cycloabscisic acid, a highly potent and long-lasting abscisic acid analogue, in radish seedlings

  摘要：

  We synthesized 5'alpha,8'-cycloabscisic acid (CycloABA), a highly potent and long-lasting abscisic acid (ABA) analogue, by a different method from that reported before. CycloABA fed to radish seedlings had more metabolic tolerance than ABA. The major metabolite of CycloABA was the glucose conjugate, which was the minor metabolite of ABA. The 8'-hydroxylated metabolite and its cyclized isomer, which were major metabolites of ABA, were not found as metabolites of CycloABA. The present results suggest that the highly potent and long-lasting activity of CycloABA is caused by resistance to ABA 8'-hydroxylase, and that CycloABA is partially metabolized to the glucose conjugate by ABA glucosyltransferase. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2003.10.048

文献信息

• Ring conformational requirement for biological activity of abscisic acid probed by the cyclopropane analogues
  作者：Yasushi Todoroki、Sei-ichi Nakano、Nobuhiro Hirai、Hajime Ohigashi

  DOI：10.1016/0040-4020(96)00371-7

  日期：1996.6

  requirement for the biological activity of abscisic acid, the cyclopropane analogues 6, 7, 9, and 10 were synthesized and their biological activities in four bioassays were tested. The activity of the achiral cyclohexadienone analogue 8 also was examined. Analogue 7 in which the 6′ β-substituent is constrained essentially to the axial-like orientation between axial and bisectional showed no activity, while 6

  为了研究对脱落酸的生物活性构象环需求，环丙烷类似物6，7，9，和10被合成和它们在生物测定4的生物活性进行了测试。还检查了非手性环己二酮类似物8的活性。类似物7，其中6'β-取代基基本上被约束在轴向和二等分之间的轴向样取向上，没有活性，而6和8在C-6'β处无轴状取代基，而与构象偏好无关，其表现出与脱落酸同等的活性。该结果表明，在环的β侧的轴向取代基对活性是致命的。脱落酸的活性构象是C-9'是赤道的且侧链在假轴和双节之间的构象，即与假链的侧链接近的偏爱的半椅子而不是较少的构象。偏爱半椅子和侧链伪赤道仪。
• Metabolism of 5′α,8′-cycloabscisic acid, a highly potent and long-lasting abscisic acid analogue, in radish seedlings
  作者：Yasushi Todoroki、Masao Sawada、Miyuki Matsumoto、Shigeko Tsukada、Kotomi Ueno、Masatoshi Isaka、Mariko Owaki、Nobuhiro Hirai

  DOI：10.1016/j.bmc.2003.10.048

  日期：2004.1

  We synthesized 5'alpha,8'-cycloabscisic acid (CycloABA), a highly potent and long-lasting abscisic acid (ABA) analogue, by a different method from that reported before. CycloABA fed to radish seedlings had more metabolic tolerance than ABA. The major metabolite of CycloABA was the glucose conjugate, which was the minor metabolite of ABA. The 8'-hydroxylated metabolite and its cyclized isomer, which were major metabolites of ABA, were not found as metabolites of CycloABA. The present results suggest that the highly potent and long-lasting activity of CycloABA is caused by resistance to ABA 8'-hydroxylase, and that CycloABA is partially metabolized to the glucose conjugate by ABA glucosyltransferase. (C) 2003 Elsevier Ltd. All rights reserved.