[(1S,2S,4R,6R,8S,9R,10R,13R,14R,17S)-8-hydroxy-2,8,10,13,18,18-hexamethyl-6-[(1R)-2-methyl-1-[(2S)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoyl]oxyprop-2-enyl]-12-oxo-5-oxapentacyclo[11.8.0.02,10.04,9.014,19]henicos-19-en-17-yl] (2S)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoate | 1354781-54-6

• 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: [(1S,2S,4R,6R,8S,9R,10R,13R,14R,17S)-8-hydroxy-2,8,10,13,18,18-hexamethyl-6-[(1R)-2-methyl-1-[(2S)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoyl]oxyprop-2-enyl]-12-oxo-5-oxapentacyclo[11.8.0.02,10.04,9.014,19]henicos-19-en-17-yl] (2S)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoate
• CAS: 1354781-54-6
• 化学式: C₅₀H₆₀F₆O₉
• 分子量: 919.011
• InChiKey: QTPOAQOILBHYDI-PBIQTUDGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10
• 重原子数：
  65
• 可旋转键数：
  12
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  118
• 氢给体数：
  1
• 氢受体数：
  15

反应信息

• 作为产物：
  描述：

  (3S,8S,9R,10R,13R,14S,16R,17R,21S,23R,24R)-16,23-epoxy-3,20,24-trihydroxycucurbit-5,25(27)-dien-11-one 、 (R)-methoxytrifluoromethylphenylacetyl chloride 以 氘代吡啶 为溶剂， 生成 [(1S,2S,4R,6R,8S,9R,10R,13R,14R,17S)-8-hydroxy-2,8,10,13,18,18-hexamethyl-6-[(1R)-2-methyl-1-[(2S)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoyl]oxyprop-2-enyl]-12-oxo-5-oxapentacyclo[11.8.0.02,10.04,9.014,19]henicos-19-en-17-yl] (2S)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoate
  参考文献：
  名称：

  Isolation, Structure Elucidation, and Biological Evaluation of 16,23-Epoxycucurbitacin Constituents fromEleaocarpus chinensis

  摘要：

  Eight new 16,23-epoxycucurbitacin derivatives, designated as elaeocarpucins A-H (1-8), and five known cucurbitacins (9-13) were isolated from the chloroform-soluble partitions of separate methanol extracts of the fruits and stem bark of Elaeocarpus chinensis collected in Vietnam. Isolation work was facilitated using a LC/MS dereplication procedure, and bioassay-guided fractionation was monitored using HT-29 human cancer cells. The structures of compounds 1-8 were determined on the basis of spectroscopic data interpretation, with the absolute configurations of isomers 1 and 2 established by the Mosher ester method. Compounds 1-13 were evaluated in vitro against the HT-29 cell line and using a mitochondrial transmembrane potential assay. Elaeocarpucin C (3), produced by partial synthesis from 16 alpha,23 alpha-epoxy-3 beta,20 beta-dihydroxy-10 alpha H,23 beta H-cucurbit-5,24-dien-11-one (13), was found to be inactive when evaluated in an in vivo hollow fiber assay using three different cancer cell types (dose range 0.5-10 mg/kg/day, ip).

  DOI：

  10.1021/np200879p