(3A,5A,17B)-雄甾烷-3,17-二醇17-(氢硫酸酯) | 24869-99-6

• 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
• 中文名称: (3A,5A,17B)-雄甾烷-3,17-二醇17-(氢硫酸酯)
• 中文别名: 二乙基(diphenylmethylene)丙二酸酯
• 英文名称: 5-androstene-3,17-diol-3-sulfate
• 英文别名: 3α-hydroxy-5α-androstane-17β-sulfate；5alpha-Androstane-3alpha,17beta-diol 17-monosulfate；[(3R,5S,8R,9S,10S,13S,14S,17S)-3-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl] hydrogen sulfate
• CAS: 24869-99-6
• 化学式: C₁₉H₃₂O₅S
• 分子量: 372.526
• InChiKey: KWYNDVHEQWYGIL-KHOSGYARSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 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：

  Dihydrotestosterone sulphate 在 potassium phosphate 、 recombinant human aldo-keto reductase 1C₂ 、 还原型辅酶II(NADPH)四钠盐 作用下， 以 甲醇 为溶剂， 生成 (3A,5A,17B)-雄甾烷-3,17-二醇17-(氢硫酸酯)
  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

• Therapeutic Treatment Methods
  申请人：Reading L. Christopher

  公开号：US20070275937A1

  公开（公告）日：2007-11-29

  The invention relates to the use of compounds to ameliorate or treat a condition such as a cystic fibrosis, neutropenia or other exemplified conditions. Exemplary compounds that can be used include 3β-hydroxy-17β-aminoandrost-5-ene, 3β-hydroxy-16α-fluoro-17β-aminoandrost-5-ene, 3α-hydroxy-16α-fluoro-17β-aminoandrost-5-ene, 3β-hydroxy-16β-fluoro-17β-aminoandrost-5-ene, 1α,3β-dihydroxy-4α-fluoroandrost-5-ene-17-one, 1α,3β,17β-trihydroxy-4α-fluoroandrost-5-ene, 1β,3β-dihydroxy-6α-bromoandrost-5-ene, 1α-fluoro-3β,12α-dihydroxyandrost-5-ene-17-one, 1α-fluoro-3β,4α-dihydroxyandrost-5-ene and 4α-fluoro-3β,6α,17β-trihydroxyandrostane.
• US7482334B2
  申请人：——

  公开号：US7482334B2

  公开（公告）日：2009-01-27
• US7547687B2
  申请人：——

  公开号：US7547687B2

  公开（公告）日：2009-06-16
• 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.