3α-hydroxy-5β-estran-17-one glucuronide

• 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-hydroxy-5β-estran-17-one glucuronide
• 英文别名: 5β-estran-17-one-3α-O-glucuronide；19-Noretiocholanolone glucuronide；(2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-[[(3R,5R,8R,9R,10S,13S,14S)-13-methyl-17-oxo-2,3,4,5,6,7,8,9,10,11,12,14,15,16-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]oxane-2-carboxylic acid
• 化学式: C₂₄H₃₆O₈
• 分子量: 452.545
• InChiKey: JGNAYBFRYHOLMC-HAVPAZTRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  32
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  134
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  诺龙 、 6-[[[5-(2,4-二氧代嘧啶-1-基)-3,4-二羟基四氢呋喃-2-基]甲氧基-羟基磷酰]氧基-羟基磷酰]氧基-3,4,5-三羟基四氢吡喃-2-羧酸 在 liver microsomes from Aroclor 1254-induced male Wistar rat 作用下， 以 甲醇 、 phosphate buffer 为溶剂， 以77%的产率得到17-Β-诺龙-葡糖苷酸钾盐
  参考文献：
  名称：

  Enzyme-assisted synthesis and structure characterization of glucuronide conjugates of eleven anabolic steroid metabolites

  摘要：

  Enzyme-assisted in vitro synthesis of eleven glucuronide-conjugated anabolic androgenic steroid (AAS) metabolites was performed using biphenyl-induced rat liver microsomal enzymes. The substrates within the study were the main compounds and metabolites detected in human urine after dosing of, e.g. metandienone, metenolone, methyltestosterone, nandrolone, and testosterone. Yields of glucuronidation reactions were 13-28% for most compounds, but significantly higher (77-78%) for the substrates with 4-ene-3-one double bond system of the steroid A-ring. Characterization of glucuronide-conjugated AAS structures was based on nuclear magnetic resonance spectroscopy (H-1 NMR) and on liquid chromatographic-mass spectrometric (LC-MS) and tandem mass spectrometric (LC-MS/MS) analyses in positive and negative ion mode electrospray ionization (ESI). Only minor differences were observed in optimal synthesis conditions between various substrates, which offer a potential to apply this in vitro assay as a default method for glucuronidation of new AAS substrates. The method allowed for a rapid production pathway of stereochemically pure AAS glucuronides in milligram amount, such as needed, e.g. in the development of analytical methods in forensic or pharmaceutical sciences, as well as in doping control. (C) 2007 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2007.10.008

文献信息

• Enzyme-assisted synthesis and structure characterization of glucuronide conjugates of eleven anabolic steroid metabolites
  作者：Laura Hintikka、Tiia Kuuranne、Olli Aitio、Mario Thevis、Wilhelm Schänzer、Risto Kostiainen

  DOI：10.1016/j.steroids.2007.10.008

  日期：2008.3

  Enzyme-assisted in vitro synthesis of eleven glucuronide-conjugated anabolic androgenic steroid (AAS) metabolites was performed using biphenyl-induced rat liver microsomal enzymes. The substrates within the study were the main compounds and metabolites detected in human urine after dosing of, e.g. metandienone, metenolone, methyltestosterone, nandrolone, and testosterone. Yields of glucuronidation reactions were 13-28% for most compounds, but significantly higher (77-78%) for the substrates with 4-ene-3-one double bond system of the steroid A-ring. Characterization of glucuronide-conjugated AAS structures was based on nuclear magnetic resonance spectroscopy (H-1 NMR) and on liquid chromatographic-mass spectrometric (LC-MS) and tandem mass spectrometric (LC-MS/MS) analyses in positive and negative ion mode electrospray ionization (ESI). Only minor differences were observed in optimal synthesis conditions between various substrates, which offer a potential to apply this in vitro assay as a default method for glucuronidation of new AAS substrates. The method allowed for a rapid production pathway of stereochemically pure AAS glucuronides in milligram amount, such as needed, e.g. in the development of analytical methods in forensic or pharmaceutical sciences, as well as in doping control. (C) 2007 Elsevier Inc. All rights reserved.