17β-hydroxy-2α-hydroxymethyl-17α-methyl-5α-androstan-3-one | 20592-44-3

• 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: 17β-hydroxy-2α-hydroxymethyl-17α-methyl-5α-androstan-3-one
• 英文别名: 17beta-Hydroxy-2alpha-(hydroxymethyl)-17-methyl-5alpha-androstan-3-one；(2S,5S,8R,9S,10S,13S,14S,17S)-17-hydroxy-2-(hydroxymethyl)-10,13,17-trimethyl-2,4,5,6,7,8,9,11,12,14,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-3-one
• CAS: 20592-44-3
• 化学式: C₂₁H₃₄O₃
• 分子量: 334.499
• InChiKey: GGRVPLDBVRRQSR-NWIHUDFTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  24
• 可旋转键数：
  1
• 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：

  17β-Hydroxy-2-(hydroxymethylene)-17-methyl-5α-androstan-3-one 在 cell-free system of Streptomyces cinereocrocatus NRRL 3443 作用下， 生成 17β-hydroxy-2α-hydroxymethyl-17α-methyl-5α-androstan-3-one
  参考文献：
  名称：

  The hydrogenation of .ALPHA.-hydroxymethylene-ketone derivatives to .ALPHA.-hydroxymethyl-ketone derivatives with a cell-free system of Streptomyces cinereocrocatus.

  摘要：

  2', 3'-二氢-5'-甲酰基银翘素（3）、羟甲酮（5）和3β-乙酰氧基-16-乙酰氧基亚甲基-5-雄甾烯-17-酮（9）被用作来自链霉菌Streptomyces cinereocrocatus NRRL 3443的无细胞系统的底物。结果表明，S. cinereocrocatus含有酶活性，可以将上述三种α-羟甲基-酮还原为相应的α-羟甲基-酮。

  DOI：

  10.1248/cpb.37.502

文献信息

• Identification of drostanolone and 17-methyldrostanolone metabolites produced by cryopreserved human hepatocytes
  作者：Julie Gauthier、Danielle Goudreault、Donald Poirier、Christiane Ayotte

  DOI：10.1016/j.steroids.2008.11.002

  日期：2009.3

  Methyldrostanolone (2 alpha,17 alpha-dimethyl-17 beta-hydroxy-5 alpha-androstan-3-one) was synthesized from drostanolone (17 beta-hydroxy-2 alpha-methyl-5 alpha-androstan-3-one) and identified in commercial products. Cultures of cryopreserved human hepatocytes were used to study the biotransformation of drostanolone and its 17-methylated derivative. For both steroids, the common 3 alpha-(major) and 3 beta-reduced metabolites were identified by GC-MS analysis of the extracted culture medium and the stereochemistry confirmed by incubation with 3 alpha-hydroxysteroid dehydrogenase. Structures corresponding to hydroxylated metabolites in C-12 (minor) and C-16 were proposed for other metabolites based upon the evaluation of the mass spectra of the pertrimethylsilyl (TMS-d(0) and TMS-d(9)) derivatives. Finally, on the basis of the GC-MS and H-1 NMR data and through chemical synthesis of the 17-methylated model compounds, structures could be proposed for metabolites hydroxylated in C-2. All the metabolites extracted from hepatocyte culture medium were present although in different relative amounts in urines collected following the administration to a human volunteer. therefore confirming the suitability of the cryopreserved hepatocytes to generate characteristic metabolites and study biotransformation of new steroids. (C) 2008 Elsevier Inc. All rights reserved.
• ODA, TAIKO;SATO, RUMIKO;SATO, YOSHIHIRO, CHEM. AND PHARM. BULL., 37,(1989) N, C. 502-505
  作者：ODA, TAIKO、SATO, RUMIKO、SATO, YOSHIHIRO

  DOI：——

  日期：——
• The hydrogenation of .ALPHA.-hydroxymethylene-ketone derivatives to .ALPHA.-hydroxymethyl-ketone derivatives with a cell-free system of Streptomyces cinereocrocatus.
  作者：Taiko ODA、Rumiko SATO、Yoshihiro SATO

  DOI：10.1248/cpb.37.502

  日期：——

  2', 3'-Dihydro-5'-formylgriseofulvin (3), oxymetholone (5), and 3β-acetoxy-16-acetoxymethylene-5-androsten-17-one (9) were used as the substrates of a cell-free system from Streptomyces cinereocrocatus NRRL 3443. The reuslts indicated that S. cinereocrocatus contains enzymatic activities which reduce the above three α-hydroxymthylene-ketones to the corresponding α-hydroxymethyl-ketones.

  2', 3'-二氢-5'-甲酰基银翘素（3）、羟甲酮（5）和3β-乙酰氧基-16-乙酰氧基亚甲基-5-雄甾烯-17-酮（9）被用作来自链霉菌Streptomyces cinereocrocatus NRRL 3443的无细胞系统的底物。结果表明，S. cinereocrocatus含有酶活性，可以将上述三种α-羟甲基-酮还原为相应的α-羟甲基-酮。