孕烷-20-酮,3,11,21-三羟基-,(3b,5b,11b)- | 27857-26-7

• 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: 孕烷-20-酮,3,11,21-三羟基-,(3b,5b,11b)-
• 英文名称: 3β.11β.21-trihydroxy-5β-pregnanone-(20)
• 英文别名: 3β.11β.21-Trihydroxy-5β-pregnanon-(20)；1-[(3S,5R,8S,9S,10S,11S,13S,14S,17S)-3,11-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-hydroxyethanone
• CAS: 27857-26-7
• 化学式: C₂₁H₃₄O₄
• 分子量: 350.499
• InChiKey: RHQQHZQUAMFINJ-QZWWJOACSA-N

物化性质

• 沸点：
  509.6±50.0 °C(Predicted)
• 密度：
  1.180±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  77.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  孕烷-20-酮,3,11,21-三羟基-,(3b,5b,11b)- 、 溶剂黄146 、 alkaline earth salt of/the/ methylsulfuric acid 生成 (+)-3,11-dioxo-5α-androstanecarboxylic acid
  参考文献：
  名称：

  关于肾上腺皮质的成分。21.沟通。物质R和S的组成

  摘要：

  DOI：

  10.1002/hlca.193802101183
• 作为产物：
  描述：

  11β,21-二羟基-5β-孕甾-3,20-二酮 在 potassium phosphate 、 rabbit aldose reductase-like protein AKR₁B₁₉ 、 烟酰胺腺嘌呤双核苷酸磷酸盐 作用下， 以 甲醇 为溶剂， 生成 孕烷-20-酮,3,11,21-三羟基-,(3b,5b,11b)-
  参考文献：
  名称：

  Characterization of rabbit aldose reductase-like protein with 3β-hydroxysteroid dehydrogenase activity

  摘要：

  In this study, we isolated the cDNA for a rabbit aldose reductase-like protein that shared an 86% sequence identity to human aldo-keto reductase (AKR)(1) 1B10 and has been assigned as AKR1B19 in the AKR superfamily. The purified recombinant AKR1B19 was similar to AKR1B10 and rabbit aldose reductase (AKR1B2) in the substrate specificity for various aldehydes and alpha-dicarbonyl compounds. In contrast to AKR1B10 and AKR1B2, AKR1B19 efficiently reduced 3-keto-5 alpha/beta-dihydro-C19/C21/C24-steroids into the corresponding 3 beta-hydroxysteroids, showing K-m of 1.3-9.1 mu M and k(cat) of 1.1-7.6 min(-1). The stereospecific reduction was also observed in the metabolism of 5 alpha- and 5 beta-dihydrotestosterones in AKR1B19-overexpressing cells. The mRNA for AKR1B19 was ubiquitously expressed in rabbit tissues, and the enzyme was co-purified with 3 beta-hydroxysteroid dehydrogenase activity from the lung. Thus, AKR1B19 may function as a 3-ketoreductase, as well as a defense system against cytotoxic carbonyl compounds in rabbit tissues. The molecular determinants for the unique 3-ketoreductase activity were investigated by replacement of Phe303 and Met304 in AKR1B19 with Gln and Ser, respectively, in AKR1B10. Single and double mutations (F303Q, M304S and F303Q/M304S) significantly impaired this activity, suggesting the two residues play critical roles in recognition of the steroidal substrate. (C) 2012 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.abb.2012.07.012

文献信息

• Über Bestandteile der Nebennierenrinde und verwandte Stoffe. (74. Mitteilung). Konfiguration der Cortico-Steroide)
  作者：J. von Euw、T. Reichstein

  DOI：10.1002/hlca.19470300124

  日期：1947.2.1
• Characterization of rabbit aldose reductase-like protein with 3β-hydroxysteroid dehydrogenase activity
  作者：Satoshi Endo、Toshiyuki Matsunaga、Sho Kumada、Airi Fujimoto、Satoshi Ohno、Ossama El-Kabbani、Dawei Hu、Naoki Toyooka、Jun’ichi Mano、Kazuo Tajima、Akira Hara

  DOI：10.1016/j.abb.2012.07.012

  日期：2012.11

  In this study, we isolated the cDNA for a rabbit aldose reductase-like protein that shared an 86% sequence identity to human aldo-keto reductase (AKR)(1) 1B10 and has been assigned as AKR1B19 in the AKR superfamily. The purified recombinant AKR1B19 was similar to AKR1B10 and rabbit aldose reductase (AKR1B2) in the substrate specificity for various aldehydes and alpha-dicarbonyl compounds. In contrast to AKR1B10 and AKR1B2, AKR1B19 efficiently reduced 3-keto-5 alpha/beta-dihydro-C19/C21/C24-steroids into the corresponding 3 beta-hydroxysteroids, showing K-m of 1.3-9.1 mu M and k(cat) of 1.1-7.6 min(-1). The stereospecific reduction was also observed in the metabolism of 5 alpha- and 5 beta-dihydrotestosterones in AKR1B19-overexpressing cells. The mRNA for AKR1B19 was ubiquitously expressed in rabbit tissues, and the enzyme was co-purified with 3 beta-hydroxysteroid dehydrogenase activity from the lung. Thus, AKR1B19 may function as a 3-ketoreductase, as well as a defense system against cytotoxic carbonyl compounds in rabbit tissues. The molecular determinants for the unique 3-ketoreductase activity were investigated by replacement of Phe303 and Met304 in AKR1B19 with Gln and Ser, respectively, in AKR1B10. Single and double mutations (F303Q, M304S and F303Q/M304S) significantly impaired this activity, suggesting the two residues play critical roles in recognition of the steroidal substrate. (C) 2012 Elsevier Inc. All rights reserved.
• Über Bestandteile der Nebennierenrinde. 21. Mitteilung. Die Konstitution der Substanzen R und S
  作者：T. Reichstein

  DOI：10.1002/hlca.193802101183

  日期：——