3α,17β-dihydroxy-5β-androstan-11-one | 1158-94-7

• 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: 3α,17β-dihydroxy-5β-androstan-11-one
• 英文别名: 11-ketoetiocholanediol；3α,17β-Dihydroxy-5β-androstan-11-on；3α,17-β-Dihydroxy-5β-androstanon-(11)；5beta-Androstan-11-one, 3alpha,17beta-dihydroxy-；(3R,5R,8S,9S,10S,13S,14S,17S)-3,17-dihydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-11-one
• CAS: 1158-94-7
• 化学式: C₁₉H₃₀O₃
• 分子量: 306.445
• InChiKey: CEMLAYQDMWFPDU-NQVCGYLFSA-N

物化性质

• 熔点：
  254-255 °C
• 沸点：
  454.7±40.0 °C(Predicted)
• 密度：
  1.158±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  22
• 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：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• WGK Germany：
  3

反应信息

• 作为反应物：
  描述：

  3α,17β-dihydroxy-5β-androstan-11-one 在 17β-hydroxysteroid dehydrogenase type 2 作用下， 生成 11-酮本胆烷醇酮
  参考文献：
  名称：

  The A-ring reduction of 11-ketotestosterone is efficiently catalysed by AKR1D1 and SRD5A2 but not SRD5A1

  摘要：

  Testosterone and its 5 alpha-reduced form, 5 alpha-dihydrotestosterone, were previously thought to represent the only active androgens in humans. However, recent studies have shown that the potent androgen, 11-ketotestosterone, derived from the adrenal androgen precursor, 110-hydroxyandrostenedione, may in fact serve as the primary androgen in healthy women. Yet, despite recent renewed interest in these steroids, their downstream metabolism has remained undetermined. We therefore set out to investigate the metabolism of 11-ketotestosterone by characterising the 5 alpha or 50-reduction commitment step. We show that inactivation of 11-ketotestosterone is predominantly driven by AKR1D1, which efficiently catalyses the 50-reduction of 11-ketotestosterone, committing it to a metabolic pathway that terminates in 11-ketoetiocholanolone. We demonstrate that 5 alpha-reduction of 11-ketotestosterone is catalysed by SRD5A2, but not SRD5A1, and terminates in 11-ketoandrosterone, but is only responsible for a minority of 11-ketotestosterone inactivation. However, as 11-ketoetiocholanolone is also generated by the metabolism of the glucocorticoid cortisone, 11-ketoandrosterone should be considered a more specific urinary marker of 11-ketotestosterone production.

  DOI：

  10.1016/j.jsbmb.2020.105724
• 作为产物：
  描述：

  3α-acetoxy-5β-androstanedione-(11.17) 在 氢氧化钾 、 溶剂黄146 、 铂 作用下， 生成 3α,17β-dihydroxy-5β-androstan-11-one
  参考文献：
  名称：

  20-酮戊烷的过苯甲酸氧化。

  摘要：

  DOI：

  10.1021/ja01203a076

文献信息

• Steroid transformations with Exophiala jeanselmei var. lecanii-corni and Ceratocystis paradoxa☆
  作者：Roy B.R Porter、Winklet A Gallimore、Paul B Reese

  DOI：10.1016/s0039-128x(99)00066-5

  日期：1999.11

  The fungi Exophiala jeanselmei var. lecanii-corni [IMI (International Mycological Institute) 312989, UAMH (University of Alberta Microfungus Collection and Herbarium) 8783] and Ceratocystis paradoxa (IMI 374529, UAMH 8784) have been examined for their potential in steroid biotransformation. The study has determined that E. jeanselmei var. lecanii-corni effected overall anti-Markovnikov hydration on dehydroisoandrosterone, and side-chain degradation on a variety of pregnanes. Both ascomycetes were found to carry out redox reactions of alcohols and ketones as well as 1,4 reduction of alpha,beta-unsaturated carbonyl systems. (C) 1999 Elsevier Science Inc. All rights reserved.
• Perbenzoic Acid Oxidation of 20-Ketopregnanes
  作者：Lewis Hastings Sarett

  DOI：10.1021/ja01203a076

  日期：1947.11
• The A-ring reduction of 11-ketotestosterone is efficiently catalysed by AKR1D1 and SRD5A2 but not SRD5A1
  作者：Lise Barnard、Nikolaos Nikolaou、Carla Louw、Lina Schiffer、Hylton Gibson、Lorna C. Gilligan、Elena Gangitano、Jacky Snoep、Wiebke Arlt、Jeremy W. Tomlinson、Karl-Heinz Storbeck

  DOI：10.1016/j.jsbmb.2020.105724

  日期：2020.9

  Testosterone and its 5 alpha-reduced form, 5 alpha-dihydrotestosterone, were previously thought to represent the only active androgens in humans. However, recent studies have shown that the potent androgen, 11-ketotestosterone, derived from the adrenal androgen precursor, 110-hydroxyandrostenedione, may in fact serve as the primary androgen in healthy women. Yet, despite recent renewed interest in these steroids, their downstream metabolism has remained undetermined. We therefore set out to investigate the metabolism of 11-ketotestosterone by characterising the 5 alpha or 50-reduction commitment step. We show that inactivation of 11-ketotestosterone is predominantly driven by AKR1D1, which efficiently catalyses the 50-reduction of 11-ketotestosterone, committing it to a metabolic pathway that terminates in 11-ketoetiocholanolone. We demonstrate that 5 alpha-reduction of 11-ketotestosterone is catalysed by SRD5A2, but not SRD5A1, and terminates in 11-ketoandrosterone, but is only responsible for a minority of 11-ketotestosterone inactivation. However, as 11-ketoetiocholanolone is also generated by the metabolism of the glucocorticoid cortisone, 11-ketoandrosterone should be considered a more specific urinary marker of 11-ketotestosterone production.