(1S,2S,4aR,4bS,6aS,11aS,11bR,13aR)-2,10-dihydroxy-1,4a,6a,11b-tetramethyl-1-[2-[(1S,6R)-1,2,6-trimethylcyclohex-2-en-1-yl]ethyl]-3,4,4b,5,6,11,11a,12,13,13a-decahydro-2H-indeno[2,1-a]phenanthrene-7-carbaldehyde | 1392823-91-4

• 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,4aR,4bS,6aS,11aS,11bR,13aR)-2,10-dihydroxy-1,4a,6a,11b-tetramethyl-1-[2-[(1S,6R)-1,2,6-trimethylcyclohex-2-en-1-yl]ethyl]-3,4,4b,5,6,11,11a,12,13,13a-decahydro-2H-indeno[2,1-a]phenanthrene-7-carbaldehyde
• CAS: 1392823-91-4
• 化学式: C₃₇H₅₄O₃
• 分子量: 546.834
• InChiKey: MZOXWCYLTZVAKF-QBBIBYMZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.6
• 重原子数：
  40
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  haliclioc acid B 以 氘代二甲亚砜 为溶剂， 反应 16.0h， 生成 (1S,2S,4aR,4bS,6aS,11aS,11bR,13aR)-2,10-dihydroxy-1,4a,6a,11b-tetramethyl-1-[2-[(1S,6R)-1,2,6-trimethylcyclohex-2-en-1-yl]ethyl]-3,4,4b,5,6,11,11a,12,13,13a-decahydro-2H-indeno[2,1-a]phenanthrene-7-carbaldehyde
  参考文献：
  名称：

  Halicloic Acids A and B Isolated from the Marine Sponge Haliclona sp. Collected in the Philippines Inhibit Indoleamine 2,3-Dioxygenase

  摘要：

  Two new merohexaprenoids, halicloic acids A (1) and B (2), have been isolated from the marine sponge Haliclona (Halichoclona) sp. collected in the Philippines. The glycolic acids 1 and 2 slowly decomposed during acquisition of NMR data to aldehydes 3 and 4, respectively, via an oxidative decarboxylation. Halicloic acid B (2) has the new rearranged "haliclane" meroterpenoid carbon skeleton. The halicloic acids 1 and 2 are indoleamine 2,3-dioxygenase inhibitors that are significantly more active than the decomposition products 3 and 4.

  DOI：

  10.1021/np300345j