UC1013 | 80-89-7

• 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
• 英文名称: UC1013
• 英文别名: 5β-pregnane-3β,20β-diol；5β-pregnane-3β,20β_F-diol；5β-Pregnan-3β,20β_F-diol；(10S)-3c-Hydroxy-10r.13c-dimethyl-17c-((R)-1-hydroxy-aethyl)-(5cH.8cH.9tH.14tH)-hexadecahydro-1H-cyclopenta[a]phenanthren；3β-Hydroxy-10.13-dimethyl-17β-((R)-1-hydroxy-aethyl)-5β-gonan；(20R)-5β-Pregnandiol-(3β.20)；5beta-Pregnane-3beta,20alpha-diol；(3S,5R,8R,9S,10S,13S,14S,17S)-17-[(1R)-1-hydroxyethyl]-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol
• CAS: 80-89-7
• 化学式: C₂₁H₃₆O₂
• 分子量: 320.516
• InChiKey: YWYQTGBBEZQBGO-KPXIBXGJSA-N

物化性质

• 沸点：
  435.9±18.0 °C(Predicted)
• 密度：
  1.053±0.06 g/cm3(Predicted)
• 熔点：
  191-193 °C(Solv: ethyl acetate (141-78-6))
• 保留指数：
  2636.2

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  UC1013 在 sodium 、 xylene 作用下， 生成 5-beta-孕甾烷-3-alpha,20-beta-二醇
  参考文献：
  名称：

  Sterols. XXII. The Pregnandiols and Pregnanolones

  摘要：

  DOI：

  10.1021/ja01290a057
• 作为产物：
  描述：

  黄体酮 在 Lindlar's catalyst 氢氧化钾 、 氢气 、 L-Selectride 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 0.67h， 生成 UC1013
  参考文献：
  名称：

  Introduction d'une fonction azotée en 14β du noyau stéroide. Application à la préparation d'une molécule cardioactive, le 14β-amino-5β-prégnane-3β,20β-diol, à partir de la progestérone et de l'acide désoxycholique

  摘要：

  DOI：

  10.1016/s0040-4020(01)89233-4

文献信息

• 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.
• Sterols. LXXXVII. Cholesterol and Sitosterol Derivatives
  作者：Russell E. Marker、Ewald Rohrmann

  DOI：10.1021/ja01860a016

  日期：1940.3
• Sapogenin transformation products and preparation of same
  申请人：PARKE DAVIS & CO

  公开号：US02352852A1

  公开（公告）日：1944-07-04
• Sterols. LI. Δ⁴-Pregnenone-3
  作者：Russell E. Marker、Elmer J. Lawson

  DOI：10.1021/ja01872a014

  日期：1939.3
• Sterols. XVIII. Preparation of epi-allo-Pregnanolone from allo-Pregnandiol
  作者：Russell E. Marker、Oliver Kamm、David M. Jones

  DOI：10.1021/ja01288a007

  日期：1937.9