gymnasterone A | 209169-57-3

• 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: gymnasterone A
• 英文别名: (2E,4E,6R)-N-[(1R,2R,5S,10R,12R,14R,15R,19R)-14-[(E,2R,5R)-5,6-dimethylhept-3-en-2-yl]-10-formyl-5,19-dihydroxy-2,15-dimethyl-8-oxo-10-pentacyclo[10.5.2.02,7.09,18.015,19]nonadeca-6,9(18)-dienyl]-4,6-dimethyldodeca-2,4-dienamide
• CAS: 209169-57-3
• 化学式: C₄₅H₆₇NO₅
• 分子量: 702.031
• InChiKey: TVFMBZOZGJABCW-ITNXSPAMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.3
• 重原子数：
  51
• 可旋转键数：
  14
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  104
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  gymnasterone A 、 4-溴苯甲酰氯 在 吡啶 作用下， 反应 12.0h， 以0.7 mg的产率得到[(1R,2R,5S,10R,12R,14R,15R,19R)-10-[[(2E,4E,6R)-4,6-dimethyldodeca-2,4-dienoyl]amino]-14-[(E,2R,5R)-5,6-dimethylhept-3-en-2-yl]-10-formyl-19-hydroxy-2,15-dimethyl-8-oxo-5-pentacyclo[10.5.2.02,7.09,18.015,19]nonadeca-6,9(18)-dienyl] 4-bromobenzoate
  参考文献：
  名称：

  Variation in Cytostatic Constituents of a Sponge-Derived Gymnascella dankaliensis by Manipulating the Carbon Source

  摘要：

  The Halichondria sponge-derived fungus, Gymnacella dankaliensis, was cultured in two different media conditions. A modified malt extract medium containing soluble starch instead of glucose resulted in two extremely unusual steroids, dankasterones A (2) and B (3), while four additional unusual steroids, gymnasterones A (4), B (5), C (6), and D (7), were isolated from the original malt extract medium. Their stereostructures have been established on the basis of spectroscopic analyses along with X-ray crystal structure analyses, modified Mosher's method, CD exciton method, and a chemical transformation. All the steroids except for 4 exhibited significant growth inhibition against the murine P388 cancer cell line. Dankasterone A (2) also exhibited potent growth inhibition against human cancer cell lines.

  DOI：

  10.1021/np070165m