5beta-Androstane-17alpha-ol-3-one | 5692-03-5

• 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: 5beta-Androstane-17alpha-ol-3-one
• 英文别名: 17α-hydroxy-5β-androstan-3-one；5β-androstane-3-one-17α-ol；17α-hydroxy-(5β)-androstan-3-one；17α-Hydroxy-5β-androstan-3-on；17α-Hydroxy-5β-androstanon-(3)；5beta-Dihydroepitestosterone；(5R,8R,9S,10S,13S,14S,17R)-17-hydroxy-10,13-dimethyl-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-one
• CAS: 5692-03-5
• 化学式: C₁₉H₃₀O₂
• 分子量: 290.446
• InChiKey: NVKAWKQGWWIWPM-BNFYIPGJSA-N

物化性质

• 熔点：
  142-144 °C
• 沸点：
  413.1±38.0 °C(Predicted)
• 密度：
  1.085±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5beta-Androstane-17alpha-ol-3-one 在 吡啶 、 sodium tetrahydroborate 、 sodium azide 、 cerium(III) chloride heptahydrate 作用下， 以 吡啶 、 甲醇 、 六甲基磷酰三胺 、 乙酸乙酯 为溶剂， 反应 41.33h， 生成 17β-azido-5β-androstan-3α-yl sulfate pyridinium
  参考文献：
  名称：

  Azido analogs of neuroactive steroids

  摘要：

  Analogs of pregnanolone (3 alpha-hydroxy-5 beta-pregnan-20-one), modified in position 17 were prepared. Compounds with 20-keto pregnane side chain replaced completely by azide (17 alpha- and 17 beta-azido-5 beta-androstan-3 alpha-ol), compounds with its part replaced (20-azido-21-nor-5 beta-pregnan-3 alpha-ol), and compounds with keto group only replaced ((20R)- and (20S)-20-azido-5 beta-pregnan-3 alpha-ol) were synthesized using tosylate displacements with sodium azide or Mitsunobu reaction with azoimide. All five azido steroids were converted into corresponding sulfates. Subsequent tests for inhibition of glutamate induced response on NMDA receptors revealed that modification of pregnanolone sulfate side chain with azide did not disturb the activity and some of sulfates tested were more active than parent compound. (C) 2011 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2011.04.008
• 作为产物：
  描述：

  醋酸去氢表雄酮 在 Lindlar's catalyst 吡啶 、 盐酸 、 氢氧化钾 、 sodium tetrahydroborate 、 氢气 、 aluminum isopropoxide 、 sodium nitrite 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 氯仿 、 环己酮 、 二甲基亚砜 、 乙酸乙酯 、 甲苯 为溶剂， 反应 164.75h， 生成 5beta-Androstane-17alpha-ol-3-one
  参考文献：
  名称：

  Preparation of Unlabelled and [3H]-Labelled Epitestosterone and Its Metabolites

  摘要：

  冷以及[³H]-标记底物和代谢物 IX - XI, XV, XVI, XX - XXII, XXIV, XXV 和 XXVIII 通过对雄甾二酮 (VIII) 和 ∆¹-去氢雄甾二酮 (XIII) 进行催化氢化制备。化合物 XXVIII 的制备关键步骤是将 3β-对甲苯磺酸酯 XXVI 和 XXX 与亚硝酸钾在二甲基亚砜中反应。

  DOI：

  10.1135/cccc19930600

文献信息

• Substrate specificity and inhibitor analyses of human steroid 5β-reductase (AKR1D1)
  作者：Mo Chen、Jason E. Drury、Trevor M. Penning

  DOI：10.1016/j.steroids.2011.01.003

  日期：2011.4

  systematically determined the substrate specificity of homogeneous human recombinant AKR1D1 using C18, C19, C21, and C27 Δ(4)-ketosteroids and assessed the pH-rate dependence of the enzyme. Our results show that AKR1D1 proficiently reduced all the steroids tested at physiological pH, indicating AKR1D1 is the only enzyme necessary for all the 5β-steroid metabolites present in humans. Substrate inhibition was observed

  人类类固醇 5β-还原酶（醛酮还原酶 1D1）催化 Δ(4)-酮类固醇的 C4-C5 双键的立体特异性 NADPH 依赖性还原，以产生 A/B 顺式环连接。这种顺式构型对于胆汁酸生物合成至关重要，并且在类固醇代谢中起着重要作用。该酶的生化特性尚未得到彻底研究，并且报告了相互矛盾的数据，部分原因是缺乏高度均一的蛋白质。在本研究中，我们使用 C18、C19、C21 和 C27 Δ(4)-酮类固醇系统地确定了同源人重组 AKR1D1 的底物特异性，并评估了酶的 pH 速率依赖性。我们的结果表明 AKR1D1 能有效减少在生理 pH 值下测试的所有类固醇，这表明 AKR1D1 是人类存在的所有 5β-类固醇代谢物所必需的唯一酶。如果 C11 位置未被取代，则使用 C18 至 C21 类固醇观察到底物抑制。这种结构活性关系可以通过 AKR1D1 晶体结构揭示的一个小的替代底物结合口袋的存在来解释。作为相关
• 5α-reduction of epitestosterone is catalysed by human SRD5A1 and SRD5A2 and increases androgen receptor transactivation
  作者：Lina Schiffer、Wiebke Arlt、Karl-Heinz Storbeck

  DOI：10.1016/j.jsbmb.2024.106516

  日期：2024.7

  the active androgen testosterone and its circulating concentrations are similar to those of testosterone in women and children. However, its biological function and pathways of metabolism remain unknown. The structural similarity to testosterone suggests a potential function in the modulation of androgen receptor signalling. It is well established that the conversion of testosterone to 5α-dihydrotestosterone

  表睾酮是活性雄激素睾酮的立体异构体，其循环浓度与女性和儿童的睾酮相似。然而，其生物学功能和代谢途径仍然未知。与睾酮的结构相似性表明其在调节雄激素受体信号传导中具有潜在功能。众所周知，睾酮转化为 5α-二氢睾酮可增强局部雄激素受体信号传导。在这项研究中，我们发现表睾酮被人类类固醇 5α-还原酶亚型 SRD5A1 和 SRD5A2 代谢为 5α-二氢表睾酮。使用两种不同的报告基因测定法来检测人类雄激素受体的反式激活，我们发现表睾酮是一种部分 AR 激动剂，并且表睾酮的 5α-还原增加了其雄激素活性。与此相符，我们发现表睾酮的 5α-还原降低了其拮抗 5α-二氢睾酮诱导的雄激素受体反式激活的能力。总之，我们提供证据表明类固醇 5α-还原酶调节表睾酮对雄激素受体信号传导的调节作用。
• Steroidal isomers with uniform mass spectra of their per-TMS derivatives: Synthesis of 17-hydroxyandrostan-3-ones, androst-1-, and -4-ene-3,17-diols
  作者：Maria K. Parr、Josef Zapp、Michael Becker、Georg Opfermann、Ulrike Bartz、Wilhelm Schänzer

  DOI：10.1016/j.steroids.2007.03.006

  日期：2007.6

  In human sports doping control analysis most of the steroids are analyzed after enzymatic hydrolysis of the glucuronides as per-trimethylsilyl (TMS) derivatives applying gas chromatography-mass spectrometry (GC-MS). According to the recommendations of the World Anti-Doping Agency the identification of analytes should be based on retention time and on mass spectrometric characterization. This study shows that the bis-TMS derivatives of 16 specific C19 steroids, namely the stereoisomers of S xi-androst-l-ene-3 xi,17 xi-diol (8 isomers), androst-4-ene-3 xi,17 xi-diol (4 isomers), and 17 xi-hydroxy-5 xi-androstan-3-one (4 isomers), reveal very similar mass spectra. As a rule, when taking the retention times, which are provided as Kovac indices for all these isomers, into account, a restriction to two or three possible isomers is possible. Reliable identification should additionally include a comparison of the retention times of the analytes with the reference compounds measured concomitantly. In some cases standard addition may be appropriate.Due to the limited availability; the above mentioned isomers were synthesized by reduction of the corresponding alpha,beta-unsaturated oxo, steroids either with K-Selectride or by catalytic hydrogenation (Pd/C as catalyst). The products of the reactions were identified by means of nuclear magnetic resonance (NMR) characterization and by further reduction to the corresponding 5 xi-androstane-3 xi,17 xi-diols and GC-MS comparison with commercially available reference standards. (c) 2007 Elsevier Inc. All rights reserved.
• Neuroactive steroids with perfluorobenzoyl group
  作者：Ivan Černý、Miloš Buděšínský、Vladimír Pouzar、Vojtěch Vyklický、Barbora Krausová、Ladislav Vyklický

  DOI：10.1016/j.steroids.2012.07.004

  日期：2012.10

  During an initial study in searching for the alternative derivatives suitable for photolabeling of neuroactive steroids, perfluorobenzoates and perfluorobenzamides in position 17 of 5 beta-androstan-3 alpha-ol were synthesized from the corresponding 17-hydroxy and 17-amino derivatives. After transformation into glutamates or sulfates, 17 alpha-epimers had comparable inhibitory activity at NMDA receptors to the natural neurosteroid (20-oxo-5 beta-pregnan-3 beta-yl sulfate), however, were more potent (2- to 36-fold) than their 17 beta-substituted analogs. In one case, fluorine in position 4' of perfluorobenzoate group was substituted with azide and activity of the final glutamate was retained comparing with the corresponding perfluorobenzoate. The series was expanded with perfluorobenzoyl derivatives of pregnanolone: Perfluorobenzamide of glutamate and perfluorobenzoate of 11 alpha-hydroxy pregnanolone were prepared and tested. From nine tested compounds, four of them exhibit very good inhibition activity and can serve as promising leads for photolabeling experiments. (c) 2012 Elsevier Inc. All rights reserved.
• Steroide und Sexualhormone. (113. Mitteilung). Untersuchungen über den Zusammenhang zwischen Konstitution und Geruch bei Steroiden
  作者：V. Prelog、L. Ruzicka、P. Meister、P. Wieland

  DOI：10.1002/hlca.660280185

  日期：——