3β,7α-Dihydroxy-5α-androstan-17-on | 25848-68-4

• 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: 3β,7α-Dihydroxy-5α-androstan-17-on
• 英文别名: 3beta-7alpha-Dihydroxy-5alpha-androstane-17-one；(3beta,5alpha,7alpha)-3,7-Dihydroxyandrostan-17-one；(3S,5R,7R,8R,9S,10S,13S,14S)-3,7-dihydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthren-17-one
• CAS: 25848-68-4
• 化学式: C₁₉H₃₀O₃
• 分子量: 306.445
• InChiKey: VFPMCLQMAUVEHD-KMQZSKAMSA-N

物化性质

• 沸点：
  454.7±45.0 °C(Predicted)
• 密度：
  1.158±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 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

反应信息

• 作为产物：
  描述：

  表雄酮 生成 3β,7α-Dihydroxy-5α-androstan-17-on 、 3β,7β-Dihydroxy-5α-androstan-17-on
  参考文献：
  名称：

  Bell,A.M. et al., Journal of the Chemical Society. Perkin transactions I, 1973, p. 2131 - 2136

  摘要：

  DOI：

文献信息

• Microbial hydroxylation of epiandrosterone by <i>Aspergillus candidus</i>
  作者：Kudret Yildirim、Ali Kuru

  DOI：10.1080/10242422.2017.1289184

  日期：2017.3.4

  work, Aspergillus candidus MRC 22634 converted epiandosterone 1 into 10 hydroxylated metabolites. A. candidus has been shown to hydroxylate 1 predominantly at C-11α, C-1α, and C-15β with minor hydroxylations occurring at C-14α and C-7α. Oxidation at C-3, reduction at C-17, and C-3 epimerization of some of the remaining substrate have also been shown. 15β-Hydroxylation and C-3 epimerization of 1 by

  摘要 在这项工作中，念珠菌 MRC 22634 将表雄酮 1 转化为 10 种羟基化代谢物。A. candidus 已显示主要在 C-11α、C-1α 和 C-15β 处羟基化 1，在 C-14α 和 C-7α 处发生少量羟基化。还显示了 C-3 处的氧化、C-17 处的还原和一些剩余底物的 C-3 差向异构化。首次报道了真菌对 1 的 15β-羟基化和 C-3 差向异构化。其中两种代谢物 1α,3α-dihydroxy-5α-androstan-17-one 4 和 15β,17β-dihydroxy-5α-androstan-3-one 7 被鉴定为新化合物。
• Hydroxylation of DHEA, androstenediol and epiandrosterone by Mortierella isabellina AM212. Evidence indicating that both constitutive and inducible hydroxylases catalyze 7α- as well as 7β-hydroxylations of 5-ene substrates
  作者：Teresa Kołek、Natalia Milecka、Alina Świzdor、Anna Panek、Agata Białońska

  DOI：10.1039/c1ob05350g

  日期：——

  underwent effective hydroxylation; 5-ene substrates – DHEA and androstenediol – were transformed into a mixture of 7α- and 7β- allyl alcohols, while epiandrosterone was converted into 7α- (mainly), 11α- and 9α- monohydroxy derivatives. Ketoconazole and cycloheximide inhibition studies suggest the presence of constitutive and substrate-induced hydroxylases in M. isabellina. On the basis of time course analysis

  DHEA的转型过程， 雄烯二醇 和 表雄甾酮在黄被孢霉AM212文化的影响。所提到的底物进行了有效的羟基化。5烯底物– DHEA和雄烯二醇 –被转化为7α-和7β-烯丙醇的混合物，而 表雄甾酮 被转化为7α-（主要是），11α-和9α-单羟基衍生物。 酮康唑和环己酰亚胺的抑制研究表明，伊萨贝拉霉中存在组成型和底物诱导的羟化酶。在时间过程的基础上分析脱氢表雄酮和雄烯二醇，烯丙基C中的氧化7 -H α和C 7 -H β键由相同的酶是一个合理的假设。
• Microbiological transformations. Part 4. Microbiological transformations of 5α-androstan-17-ones and of 17a-aza-<scp>D</scp>-homo-5α-androstan-17-ones with the fungus Cunninghamella elegans
  作者：Trevor A. Crabb、John A. Saul、Roger O. Williams

  DOI：10.1039/p19810001041

  日期：——

  The microbiological transformation of 5α-androstan-17-one, and the 3β-acetoxy- and 3α-hydroxy-derivatives, by Cunninghamella elegans is dominated by 1β,7-dihydroxylation or 7-monohydroxylation. 3α-Acetoxy-5α-androstan-17-one undergoes predominant 6β,11β-dihydroxylation. 17a-Aza-D-homo-5α-androstan-17-one and the 3α-acetoxy-derivative undergo predominant monohydroxylation at 6β or 7α, in contrast to

  秀丽隐杆线虫对5α-雄甾烷17-one，3β-乙酰氧基和3α-羟基衍生物的微生物转化主要由1β，7-二羟基化或7-单羟基化。3α-乙酰氧基-5α-雄烷-17-主要发生6β，11β-二羟基化。17a- Aza- D -homo-5α-androstan-17-one和3α-乙酰氧基衍生物在6β或7α处主要发生单羟基化反应，而3β-乙酰氧基衍生物虽然进行类似的单羟基化反应却得到良好的收率。 9α-单羟基化产物。
• Hydroxylation of DHEA and its analogues by Absidia coerulea AM93. Can an inducible microbial hydroxylase catalyze 7α- and 7β-hydroxylation of 5-ene and 5α-dihydro C19-steroids?
  作者：Natalia Milecka-Tronina、Teresa Kołek、Alina Świzdor、Anna Panek

  DOI：10.1016/j.bmc.2013.11.050

  日期：2014.1

  coerulea AM93. DHEA and androstenediol were transformed to the mixture of allyl 7-hydroxy derivatives, while EpiA and 5α-androstan-3,17-dione were converted mainly to 7α- and 7β-alcohols accompanied by 9α- and 11α-hydroxy derivatives. On the basis of (i) time course analysis of hydroxylation of the abovementioned substrates, (ii) biotransformation with resting cells at different pH, (iii) enzyme inhibition

  在本文中，我们着重研究了Absidia coerulea AM93对DHEA，雄烯二醇，表雄甾酮和5α-雄烷-3,17-二酮进行7-羟基化的过程。除此之外，我们提出了对蓝藻中类固醇的羟基化的初步分析。AM93。DHEA和雄烯二醇被转化为烯丙基7-羟基衍生物的混合物，而EpiA和5α-雄烷-3,17-二酮主要转化为7α-和7β-醇，并伴有9α-和11α-羟基衍生物。基于（i）上述底物羟基化的时程分析，（ii）在不同pH下静息细胞的生物转化，（iii）酶抑制分析以及（iv）底物C–H键之间的几何关系经历羟基化和辅因子结合的活性氧原子，但假定相同的酶可催化氧化ç 7 -H α以及为C 7 -H β在-5-烯和5α二氢C键19-类固醇。在底物的结构和羟基化的区域选择性之间观察到的相关性表明，正常的结合酶-底物复合物中可能发生7β-羟基化，而在反向反向结合复合物中则发生7α-羟基化。
• Microbial Transformation of Epiandrosterone by Aspergillus Sydowii
  作者：Kudret Yildirim、Ali Kuru

  DOI：10.3184/174751916x14786062524888

  日期：2016.12

  Incubation of epiandrosterone with Aspergillus sydowii MRC 200653 afforded ten metabolites. The fungal dehydrogenation of epiandrosterone is reported for the first time. The formation of the major metabolite, 6β-hydroxyandrost-4-ene-3,17-dione, involved first dehydrogenation to give a 4-ene and then hydroxylation at C-6β. Small amounts of the substrate were hydroxylated at C-1α, C-7α, C-7β and C-11α

  表雄酮与 Aspergillus sydowii MRC 200653 一起孵育得到 10 种代谢物。表雄酮的真菌脱氢是首次报道。主要代谢物 6β-hydroxyandrost-4-ene-3,17-dione 的形成涉及首先脱氢生成 4-ene，然后在 C-6β 处羟基化。少量底物在 C-1α、C-7α、C-7β 和 C-11α 处羟基化。