5α-androstan-17β-ol-3-one-17-glucuronide

• 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: 5α-androstan-17β-ol-3-one-17-glucuronide
• 英文别名: dihydrotestosterone glucuronide；(2S,3S,4S,5R)-6-[[(5S,8R,9S,10S,13S,14S,17S)-10,13-dimethyl-3-oxo-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
• 化学式: C₂₅H₃₈O₈
• 分子量: 466.572
• InChiKey: CLQMBSSRTBUNDV-SLEGFINRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  33
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.92
• 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：

  雄诺龙 、 糖质酸-1,4-内酯 在 recombinant human uridinne diphosphate-glucuronosyltransferase 1A₄ from HEK₂₉₃ cells 、 uridine 5'-diphosphoglucuronic acid triammonium salt 、 magnesium chloride 、 alamethicin 作用下， 以 二甲基亚砜 为溶剂， 生成 5α-androstan-17β-ol-3-one-17-glucuronide
  参考文献：
  名称：

  Glucuronidation of Dihydrotestosterone and trans-Androsterone by Recombinant UDP-Glucuronosyltransferase (UGT) 1A4: Evidence for Multiple UGT1A4 Aglycone Binding Sites

  摘要：

  UDP-葡萄糖醛酸基转移酶（UGT）1A4催化的葡萄糖醛酸化作用是一种重要的药物消除途径。虽然 UGT1A4 催化葡萄糖醛酸化的非典型动力学特征（非双曲、非迈克尔斯-门顿）偶有报道，但尚未开展系统的动力学研究来探索 UGT1A4 中是否存在多个苷元结合位点。为此，我们使用了两种位置异构体--双氢睾酮（DHT）和反式-雄甾酮（t -AND）--作为探针底物，评估了它们与 HEK293 表达的 UGT1A4 单独和在 UGT1A4 底物[他莫昔芬（TAM）或拉莫三嗪（LTG）]存在时的葡萄糖醛酸化动力学。与高亲和力 UGT1A4 底物 TAM 共同作用会对 DHT 和 t -AND 的葡萄糖醛酸化产生浓度依赖性激活/抑制作用，而低亲和力 UGT1A4 底物 LTG 则对这两个过程产生非竞争性抑制作用。然后评估了 TAM 单独和在不同浓度的 DHT 或 t -AND 存在下的葡萄糖醛酸化动力学。TAM 显示出底物抑制动力学，表明 TAM 在 UGT1A4 中可能有两个结合位点。然而，随着 DHT 或 t -AND 浓度的增加，TAM 的底物抑制动力学曲线变得更加双曲线。各种双位点动力学模型充分解释了 TAM 与 DHT 或 TAM 与 t -AND 之间的相互作用。此外，还评估了 TAM 对 LTG 葡萄糖醛酸化的影响。与 TAM 对 DHT 和 t -AND 葡萄糖醛酸化的混合效应不同，TAM 可抑制 LTG 葡萄糖醛酸化。我们的研究结果表明，UGT1A4 中存在多个苷元结合位点，这可能会以底物依赖的方式导致非典型动力学（同向和异向）。

  DOI：

  10.1124/dmd.109.028712

文献信息

• CORROSION INHIBITOR COMPOSITIONS AND METHODS OF USING SAME
  申请人：Ecolab USA Inc.

  公开号：US20170306504A1

  公开（公告）日：2017-10-26

  Disclosed are methods for inhibiting the corrosion of metal containments such as carbon-steel pipes used in oil recovery processes, the methods comprising adding urine and/or compositions comprising urine to water sources to form corrosion inhibitor compositions, and contacting metal containments with the corrosion inhibitor compositions. The water sources are for example aqueous solutions that are corrosive to metal containments such as carbon-steel pipes. Compositions comprising urine that provide reduced corrosion or corrosion inhibition are also described. Metal containment assemblages comprising corrosion inhibitor compositions and a metal containment are also described.
• [EN] CORROSION INHIBITOR COMPOSITIONS AND METHODS OF USING SAME<br/>[FR] COMPOSITIONS INHIBITRICES DE LA CORROSION ET LEURS PROCÉDÉS D'UTILISATION
  申请人：ECOLAB USA INC

  公开号：WO2017189528A1

  公开（公告）日：2017-11-02

  Disclosed are methods for inhibiting the corrosion of metal containments such as carbon-steel pipes used in oil recovery processes, the methods comprising adding urine and/or compositions comprising urine to water sources to form corrosion inhibitor compositions, and contacting metal containments with the corrosion inhibitor compositions. The water sources are for example aqueous solutions that are corrosive to metal containments such as carbon-steel pipes. Compositions comprising urine that provide reduced corrosion or corrosion inhibition are also described. Metal containment assemblages comprising corrosion inhibitor compositions and a metal containment are also described.
• Glucuronidation of Dihydrotestosterone and <i>trans</i>-Androsterone by Recombinant UDP-Glucuronosyltransferase (UGT) 1A4: Evidence for Multiple UGT1A4 Aglycone Binding Sites
  作者：Jin Zhou、Timothy S. Tracy、Rory P. Remmel

  DOI：10.1124/dmd.109.028712

  日期：2010.3

  UDP-glucuronosyltransferase (UGT) 1A4-catalyzed glucuronidation is an important drug elimination pathway. Although atypical kinetic profiles (nonhyperbolic, non-Michaelis-Menten) of UGT1A4-catalyzed glucuronidation have been reported occasionally, systematic kinetic studies to explore the existence of multiple aglycone binding sites in UGT1A4 have not been conducted. To this end, two positional isomers, dihydrotestosterone (DHT) and trans -androsterone ( t -AND), were used as probe substrates, and their glucuronidation kinetics with HEK293-expressed UGT1A4 were evaluated both alone and in the presence of a UGT1A4 substrate [tamoxifen (TAM) or lamotrigine (LTG)]. Coincubation with TAM, a high-affinity UGT1A4 substrate, resulted in a concentration-dependent activation/inhibition effect on DHT and t -AND glucuronidation, whereas LTG, a low-affinity UGT1A4 substrate, noncompetitively inhibited both processes. The glucuronidation kinetics of TAM were then evaluated both alone and in the presence of different concentrations of DHT or t -AND. TAM displayed substrate inhibition kinetics, suggesting that TAM may have two binding sites in UGT1A4. However, the substrate inhibition kinetic profile of TAM became more hyperbolic as the DHT or t -AND concentration was increased. Various two-site kinetic models adequately explained the interactions between TAM and DHT or TAM and t -AND. In addition, the effect of TAM on LTG glucuronidation was evaluated. In contrast to the mixed effect of TAM on DHT and t -AND glucuronidation, TAM inhibited LTG glucuronidation. Our results suggest that multiple aglycone binding sites exist within UGT1A4, which may result in atypical kinetics (both homotropic and heterotropic) in a substrate-dependent fashion.

  UDP-葡萄糖醛酸基转移酶（UGT）1A4催化的葡萄糖醛酸化作用是一种重要的药物消除途径。虽然 UGT1A4 催化葡萄糖醛酸化的非典型动力学特征（非双曲、非迈克尔斯-门顿）偶有报道，但尚未开展系统的动力学研究来探索 UGT1A4 中是否存在多个苷元结合位点。为此，我们使用了两种位置异构体--双氢睾酮（DHT）和反式-雄甾酮（t -AND）--作为探针底物，评估了它们与 HEK293 表达的 UGT1A4 单独和在 UGT1A4 底物[他莫昔芬（TAM）或拉莫三嗪（LTG）]存在时的葡萄糖醛酸化动力学。与高亲和力 UGT1A4 底物 TAM 共同作用会对 DHT 和 t -AND 的葡萄糖醛酸化产生浓度依赖性激活/抑制作用，而低亲和力 UGT1A4 底物 LTG 则对这两个过程产生非竞争性抑制作用。然后评估了 TAM 单独和在不同浓度的 DHT 或 t -AND 存在下的葡萄糖醛酸化动力学。TAM 显示出底物抑制动力学，表明 TAM 在 UGT1A4 中可能有两个结合位点。然而，随着 DHT 或 t -AND 浓度的增加，TAM 的底物抑制动力学曲线变得更加双曲线。各种双位点动力学模型充分解释了 TAM 与 DHT 或 TAM 与 t -AND 之间的相互作用。此外，还评估了 TAM 对 LTG 葡萄糖醛酸化的影响。与 TAM 对 DHT 和 t -AND 葡萄糖醛酸化的混合效应不同，TAM 可抑制 LTG 葡萄糖醛酸化。我们的研究结果表明，UGT1A4 中存在多个苷元结合位点，这可能会以底物依赖的方式导致非典型动力学（同向和异向）。