(1R,3S,5Z)-5-[(2E)-2-[(1R,3aS,8aS)-1-[(2R)-6-羟基-6-甲基庚烷-2-基]-8a-甲基-1,2,3,3a,4,6,7,8-八氢薁-5-亚基]亚乙基]-4-亚甲基环己烷-1,3-二醇 | 145459-22-9

• 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
• 中文名称: (1R,3S,5Z)-5-[(2E)-2-[(1R,3aS,8aS)-1-[(2R)-6-羟基-6-甲基庚烷-2-基]-8a-甲基-1,2,3,3a,4,6,7,8-八氢薁-5-亚基]亚乙基]-4-亚甲基环己烷-1,3-二醇
• 英文名称: (5Z,7E)-(1S,3R)-8(14)a-homo-9,10-secocholesta-5,7,10(19)-triene-1,3,25-triol<8(14)a-homocalcitriol>
• 英文别名: ZK 150123；8(14)a-Homocalcitriol；(1R,3S,5Z)-5-[(2E)-2-[(1R,3aS,8aS)-1-[(2R)-6-hydroxy-6-methylheptan-2-yl]-8a-methyl-1,2,3,3a,4,6,7,8-octahydroazulen-5-ylidene]ethylidene]-4-methylidenecyclohexane-1,3-diol
• CAS: 145459-22-9
• 化学式: C₂₈H₄₆O₃
• 分子量: 430.671
• InChiKey: WGTOPFVLLJBMFZ-QXTVKLKRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  60.7
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  <1R,<1α(R^*),3aβ,8aα>>-octahydro-8a-methyl-1-<1,5-dimethyl-5-<(trimethylsilyl)oxy>hexyl>-5(1H)-azulenone 在 正丁基锂 、 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 2.5h， 生成 (1R,3S,5Z)-5-[(2E)-2-[(1R,3aS,8aS)-1-[(2R)-6-羟基-6-甲基庚烷-2-基]-8a-甲基-1,2,3,3a,4,6,7,8-八氢薁-5-亚基]亚乙基]-4-亚甲基环己烷-1,3-二醇
  参考文献：
  名称：

  Synthesis and biological activities of 8(14)a-homocalcitriol

  摘要：

  8(14)a-Homocalcitriol was synthesized and tested for its biologic activities. It exhibited a vitamin D agonist activity profile. The compound was bound to the pig intestinal receptor with an affinity slightly less than calcitriol, showed the same potency in inducing HL 60 cell differentiation and inhibition of keratinocyte proliferation as calcitriol, and was found to be approximately 10-fold less potent in inducing hypercalcemia and hypercalciuria after a single injection in normal rats.

  DOI：

  10.1016/0039-128x(92)90099-u

文献信息

• Synthesis and biological activities of 8(14)a-homocalcitriol
  作者：Andreas Steinmeyer、Günter Neef、Gerald Kirsch、Katica Schwarz、Petra Rach、Martin Haberey、Ruth Thieroff-Ekerdt

  DOI：10.1016/0039-128x(92)90099-u

  日期：1992.9

  8(14)a-Homocalcitriol was synthesized and tested for its biologic activities. It exhibited a vitamin D agonist activity profile. The compound was bound to the pig intestinal receptor with an affinity slightly less than calcitriol, showed the same potency in inducing HL 60 cell differentiation and inhibition of keratinocyte proliferation as calcitriol, and was found to be approximately 10-fold less potent in inducing hypercalcemia and hypercalciuria after a single injection in normal rats.