孕甾烷醇酮3-beta-D-葡糖苷酸 | 31329-54-1

• 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
• 中文名称: 孕甾烷醇酮3-beta-D-葡糖苷酸
• 中文别名: 孕烷酮3-β-D-葡糖醛酸
• 英文名称: pregnanolone glucuronide
• 英文别名: 3α-hydroxy-5β-pregnane-20-one-3-glucuronide；Pregnanolone 3-b-D-Glucuronide；(2S,3S,4S,5R,6R)-6-[[(3R,5R,8R,9S,10S,13S,14S,17S)-17-acetyl-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
• CAS: 31329-54-1
• 化学式: C₂₇H₄₂O₈
• 分子量: 494.626
• InChiKey: MTPPQBWTGIHMPB-IAIFGNTJSA-N

物化性质

• 沸点：
  663.2±55.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿（少许）、DMSO（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  35
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  134
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  黄体酮 在 phosphate buffer 、 (S)-2-[3]pyridyl-pyrrolidine-1-carboxylic acid amide 、 Α-D-吡喃葡萄糖6-磷酸 、 bovine liver tissue supernatant 、 烟酰胺腺嘌呤双核苷酸磷酸盐 、 UDP-glucuronic acid 作用下， 反应 5.0h， 以4%的产率得到5beta-孕甾烷-3,20-二酮
  参考文献：
  名称：

  Metabolism and conjugation of [4-14C]progesterone by bovine liver and adipose tissues, in vitro

  摘要：

  The ability of bovine liver and fat to metabolize progesterone and also to form glucuronide conjugates with these progestins in vitro was investigated. Tissue supernatants were incubated with [4-14C] progesterone, UDP-glucuronic acid, and a NADPH generating system for 5 hr, at 37 degrees C. Steroids were identified by thin-layer chromatography, high performance liquid chromatography, and recrystallization to a constant specific activity. The total original radioactivity which could not be removed by exhaustive ether extraction (presumptive conjugates) was 44.7 +/- 14.2% in liver, 5.0 +/- 3.6% in subcutaneous fat, and 3.7 +/- 2.2% in kidney fat samples. Progestins identified in liver samples include 5 beta-pregnane-3 alpha, 20 alpha-diol (free and conjugate), 5 beta-pregnane-3 alpha, 20 beta-diol (free and conjugate), 3 alpha-hydroxy-5 beta-pregnan-20-one (free and conjugate), 3 beta-hydroxy-5 beta-pregnan-20-one (free), 5 beta-pregnane-3,20-dione (free), and progesterone (conjugate). Progestins identified in both the free and conjugate fractions of subcutaneous fat and kidney fat samples include progesterone, 3 alpha-hydroxy-5 beta-pregnan-20-one, 20 beta-hydroxy-4-pregnen-3-one, and 20 alpha-hydroxy-4-pregnen-3-one. Differences due to sex of bovine used were noted. These results confirm the ability of bovine liver to readily metabolize progesterone and form glucuronide conjugates of these compounds and suggest that adipose tissues take an active role in these actions in cattle.

  DOI：

  10.1016/0039-128x(82)90041-1