[(3R,7R,8R,9S,13S,14S,17R)-17-Ethynyl-3-hydroxy-7,13-dimethyl-2,3,4,6,7,8,9,11,12,14,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl] hydrogen sulfate | 144466-05-7

• 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: [(3R,7R,8R,9S,13S,14S,17R)-17-Ethynyl-3-hydroxy-7,13-dimethyl-2,3,4,6,7,8,9,11,12,14,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl] hydrogen sulfate
• 英文别名: [(3R,7R,8R,9S,13S,14S,17R)-17-ethynyl-3-hydroxy-7,13-dimethyl-2,3,4,6,7,8,9,11,12,14,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl] hydrogen sulfate
• CAS: 144466-05-7
• 化学式: C₂₁H₃₀O₅S
• 分子量: 394.532
• InChiKey: VQVIWQODXFIRSA-CZTKNSHGSA-N

物化性质

• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  92.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  tibolone-17β-sulfate 在 potassium phosphate 、 recombinant human aldo-keto reductase 1C₄ 、 还原型辅酶II(NADPH)四钠盐 作用下， 以 甲醇 为溶剂， 生成 [(3R,7R,8R,9S,13S,14S,17R)-17-Ethynyl-3-hydroxy-7,13-dimethyl-2,3,4,6,7,8,9,11,12,14,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl] hydrogen sulfate 、
  参考文献：
  名称：

  Liquid chromatography–mass spectrometry (LC–MS) of steroid hormone metabolites and its applications

  摘要：

  Advances in liquid chromatography-mass spectrometry (LC-MS) can be used to measure steroid hormone metabolites in vitro and in vivo. We find that LC-electrospray ionization (ESI)-MS using a LCQ ion trap mass spectrometer in the negative ion mode can be used to monitor the product profile that results from 5 alpha-dihydrotestosterone (DHT)-17 beta-glucuronide, DHT-17 beta-sulfate, and tibolone-17 beta-sulfate reduction catalyzed by human members of the aldo-keto reductase (AKR) 1C subfamily and assign kinetic constants to these reactions. We also developed a stable isotope dilution LC-electron capture atmospheric pressure chemical ionization (ECAPCI)-MS method for the quantitative analysis of estrone (El)) and its metabolites as pentafluorobenzyl (PFB) derivatives in human plasma in the attomole range. The limit of detection for E1-PFB was 740 attomole on column. Separations can be performed using normal-phase LC because ionization takes place in the gas phase rather than in solution. This permits efficient separation of the regioisomeric 2- and 4-methoxy-E1. The method was validated for the simultaneous analysis of plasma E2 and its metabolites: 2-methoxy-E2, 4-methoxy-E2, 16 alpha-hydroxy-E2, estrone (E1), 2-methoxy-E1, 4-methoxy-E1, and 16 alpha-hydroxy-E1 from 5 pg/mL to 2000 pg/mL. Our LC-MS methods have sufficient sensitivity to detect steroid hormone levels in prostate and breast tumors and should aid their molecular diagnosis and treatment. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.jsbmb.2010.01.005

文献信息

• Liquid chromatography–mass spectrometry (LC–MS) of steroid hormone metabolites and its applications
  作者：Trevor M. Penning、Seon-Hwa Lee、Yi Jin、Alejandro Gutierrez、Ian A. Blair

  DOI：10.1016/j.jsbmb.2010.01.005

  日期：2010.8

  Advances in liquid chromatography-mass spectrometry (LC-MS) can be used to measure steroid hormone metabolites in vitro and in vivo. We find that LC-electrospray ionization (ESI)-MS using a LCQ ion trap mass spectrometer in the negative ion mode can be used to monitor the product profile that results from 5 alpha-dihydrotestosterone (DHT)-17 beta-glucuronide, DHT-17 beta-sulfate, and tibolone-17 beta-sulfate reduction catalyzed by human members of the aldo-keto reductase (AKR) 1C subfamily and assign kinetic constants to these reactions. We also developed a stable isotope dilution LC-electron capture atmospheric pressure chemical ionization (ECAPCI)-MS method for the quantitative analysis of estrone (El)) and its metabolites as pentafluorobenzyl (PFB) derivatives in human plasma in the attomole range. The limit of detection for E1-PFB was 740 attomole on column. Separations can be performed using normal-phase LC because ionization takes place in the gas phase rather than in solution. This permits efficient separation of the regioisomeric 2- and 4-methoxy-E1. The method was validated for the simultaneous analysis of plasma E2 and its metabolites: 2-methoxy-E2, 4-methoxy-E2, 16 alpha-hydroxy-E2, estrone (E1), 2-methoxy-E1, 4-methoxy-E1, and 16 alpha-hydroxy-E1 from 5 pg/mL to 2000 pg/mL. Our LC-MS methods have sufficient sensitivity to detect steroid hormone levels in prostate and breast tumors and should aid their molecular diagnosis and treatment. (C) 2010 Elsevier Ltd. All rights reserved.