3-oxo-4-pregnene-20-carboxylic acid | 115208-40-7

• 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: 3-oxo-4-pregnene-20-carboxylic acid
• 英文别名: 2-[(8R,9S,10S,13S,14S,17R)-10,13-dimethyl-3-oxo-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]propanoic acid
• CAS: 115208-40-7
• 化学式: C₂₂H₃₄O₃
• 分子量: 346.51
• InChiKey: KCECQKDCNBQCKQ-BBRZLJIMSA-N

物化性质

• 沸点：
  486.2±18.0 °C(Predicted)
• 密度：
  1.091±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  stigmasta-4,22-dien-3-one 在 臭氧 、 吡啶 作用下， 以 二氯甲烷 为溶剂， 生成 3-oxo-4-pregnene-20-carboxylic acid
  参考文献：
  名称：

  Pathway Profiling in Mycobacterium tuberculosis

  摘要：

  Mycobacterium tuberculosis, the bacterium that causes tuberculosis, imports and metabolizes host cholesterol during infection. This ability is important in the chronic phase of infection. Here we investigate the role of the intracellular growth operon (igr), which has previously been identified as having a cholesterol-sensitive phenotype in vitro and which is important for intracellular growth of the mycobacteria. We have employed isotopically labeled low density lipoproteins containing either [1,7,15,22,26-C-14] cholesterol or [1,7,15,22,26-C-13] cholesterol and high resolution LC/MS as tools to profile the cholesterol-derived metabolome of an igr operon-disrupted mutant (Delta igr) of M. tuberculosis. A partially metabolized cholesterol species accumulated in the Delta igr knock-out strain that was absent in the complemented and parental wild-type strains. Structural elucidation by multidimensional H-1 and C-13 NMR spectroscopy revealed the accumulated metabolite to be methyl 1 beta-(2'-propanoate)-3a alpha-H-4 alpha-(3'-propanoic acid)-7a beta-methylhexahydro5-indanone. Heterologously expressed and purified FadE28-FadE29, an acyl-CoA dehydrogenase encoded by the igr operon, catalyzes the dehydrogenation of 2'-propanoyl-CoA ester side chains in substrates with structures analogous to the characterized metabolite. Based on the structure of the isolated metabolite, enzyme activity, and bioinformatic annotations, we assign the primary function of the igr operon to be degradation of the 2'-propanoate side chain. Therefore, the igr operon is necessary to completely metabolize the side chain of cholesterol metabolites.

  DOI：

  10.1074/jbc.m111.313643

文献信息

• Neue mehrfach ungesättigte BNC-Halogenide und Verfahren zu ihrer Herstellung
  申请人：Henkel Kommanditgesellschaft auf Aktien

  公开号：EP0034248B1

  公开（公告）日：1984-07-25
• Pathway Profiling in Mycobacterium tuberculosis
  作者：Suzanne T. Thomas、Brian C. VanderVen、David R. Sherman、David G. Russell、Nicole S. Sampson

  DOI：10.1074/jbc.m111.313643

  日期：2011.12

  Mycobacterium tuberculosis, the bacterium that causes tuberculosis, imports and metabolizes host cholesterol during infection. This ability is important in the chronic phase of infection. Here we investigate the role of the intracellular growth operon (igr), which has previously been identified as having a cholesterol-sensitive phenotype in vitro and which is important for intracellular growth of the mycobacteria. We have employed isotopically labeled low density lipoproteins containing either [1,7,15,22,26-C-14] cholesterol or [1,7,15,22,26-C-13] cholesterol and high resolution LC/MS as tools to profile the cholesterol-derived metabolome of an igr operon-disrupted mutant (Delta igr) of M. tuberculosis. A partially metabolized cholesterol species accumulated in the Delta igr knock-out strain that was absent in the complemented and parental wild-type strains. Structural elucidation by multidimensional H-1 and C-13 NMR spectroscopy revealed the accumulated metabolite to be methyl 1 beta-(2'-propanoate)-3a alpha-H-4 alpha-(3'-propanoic acid)-7a beta-methylhexahydro5-indanone. Heterologously expressed and purified FadE28-FadE29, an acyl-CoA dehydrogenase encoded by the igr operon, catalyzes the dehydrogenation of 2'-propanoyl-CoA ester side chains in substrates with structures analogous to the characterized metabolite. Based on the structure of the isolated metabolite, enzyme activity, and bioinformatic annotations, we assign the primary function of the igr operon to be degradation of the 2'-propanoate side chain. Therefore, the igr operon is necessary to completely metabolize the side chain of cholesterol metabolites.