(5S,8R,9S,10S,13S,14S,17S)-17-Hydroxy-10,13,17-trimethyl-3-oxo-hexadecahydro-cyclopenta[a]phenanthrene-2-carboxylic acid

• 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: (5S,8R,9S,10S,13S,14S,17S)-17-Hydroxy-10,13,17-trimethyl-3-oxo-hexadecahydro-cyclopenta[a]phenanthrene-2-carboxylic acid
• 英文别名: (5S,8R,9S,10S,13S,14S,17S)-17-hydroxy-10,13,17-trimethyl-3-oxo-2,4,5,6,7,8,9,11,12,14,15,16-dodecahydro-1H-cyclopenta[a]phenanthrene-2-carboxylic acid
• 化学式: C₂₁H₃₂O₄
• 分子量: 348.483
• InChiKey: OUOPIDHLKVJXSK-PFYHNXQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  25
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  重氮甲烷 、 (5S,8R,9S,10S,13S,14S,17S)-17-Hydroxy-10,13,17-trimethyl-3-oxo-hexadecahydro-cyclopenta[a]phenanthrene-2-carboxylic acid 在 lithium diisopropyl amide 作用下， 生成
  参考文献：
  名称：

  Studies on anabolic steroids. 10. Synthesis and identification of acidic urinary metabolites of oxymetholone in a human11Part 9 of this paper is in press (itSteroids vol 57, 1992).

  摘要：

  Two major unconjugated acidic metabolites of oxymetholone (17-beta-hydroxy-2-hydroxymethylene-17-alpha-methyl-5-alpha-androstan-3-one, 1), namely, 17-beta-hydroxy-17-alpha-methyl-2,3-seco-5-alpha-androstane-2,3-dioic acid (2) and 3-alpha,17-beta-dihydroxy-17-alpha-methyl-5-alpha-androstane-2-beta-carboxylic acid (6a), were detected by gas chromatography/mass spectrometry in urine samples collected after oral administration of 1 to a human volunteer. Reference steroid 2 was synthesized and identified. The identification of urinary metabolite 6a was based on the synthesis of its stereoisomers and the isomerization of the methyl ester 6b to its 2-epimer, 3-alpha,17-beta-dihydroxy-17-alpha-methyl-5-alpha-androstane-2-alpha-carboxylic acid methyl ester (9b). The mechanisms accounting for the formation of these acidic metabolites are discussed.

  DOI：

  10.1016/0039-128x(92)90100-n
• 作为产物：
  描述：

  美雄诺龙 、 碳酸镁 在 盐酸 作用下， 生成 (5S,8R,9S,10S,13S,14S,17S)-17-Hydroxy-10,13,17-trimethyl-3-oxo-hexadecahydro-cyclopenta[a]phenanthrene-2-carboxylic acid
  参考文献：
  名称：

  Studies on anabolic steroids. 10. Synthesis and identification of acidic urinary metabolites of oxymetholone in a human11Part 9 of this paper is in press (itSteroids vol 57, 1992).

  摘要：

  Two major unconjugated acidic metabolites of oxymetholone (17-beta-hydroxy-2-hydroxymethylene-17-alpha-methyl-5-alpha-androstan-3-one, 1), namely, 17-beta-hydroxy-17-alpha-methyl-2,3-seco-5-alpha-androstane-2,3-dioic acid (2) and 3-alpha,17-beta-dihydroxy-17-alpha-methyl-5-alpha-androstane-2-beta-carboxylic acid (6a), were detected by gas chromatography/mass spectrometry in urine samples collected after oral administration of 1 to a human volunteer. Reference steroid 2 was synthesized and identified. The identification of urinary metabolite 6a was based on the synthesis of its stereoisomers and the isomerization of the methyl ester 6b to its 2-epimer, 3-alpha,17-beta-dihydroxy-17-alpha-methyl-5-alpha-androstane-2-alpha-carboxylic acid methyl ester (9b). The mechanisms accounting for the formation of these acidic metabolites are discussed.

  DOI：

  10.1016/0039-128x(92)90100-n

文献信息

• Studies on anabolic steroids. 10. Synthesis and identification of acidic urinary metabolites of oxymetholone in a human11Part 9 of this paper is in press (itSteroids vol 57, 1992).
  作者：Honggang Bi、Robert Massé、George Just

  DOI：10.1016/0039-128x(92)90100-n

  日期：1992.9

  Two major unconjugated acidic metabolites of oxymetholone (17-beta-hydroxy-2-hydroxymethylene-17-alpha-methyl-5-alpha-androstan-3-one, 1), namely, 17-beta-hydroxy-17-alpha-methyl-2,3-seco-5-alpha-androstane-2,3-dioic acid (2) and 3-alpha,17-beta-dihydroxy-17-alpha-methyl-5-alpha-androstane-2-beta-carboxylic acid (6a), were detected by gas chromatography/mass spectrometry in urine samples collected after oral administration of 1 to a human volunteer. Reference steroid 2 was synthesized and identified. The identification of urinary metabolite 6a was based on the synthesis of its stereoisomers and the isomerization of the methyl ester 6b to its 2-epimer, 3-alpha,17-beta-dihydroxy-17-alpha-methyl-5-alpha-androstane-2-alpha-carboxylic acid methyl ester (9b). The mechanisms accounting for the formation of these acidic metabolites are discussed.