4alpha-Methyl-5alpha-cholesta-8,24-dien-3-one | 7377-73-3

• 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: 4alpha-Methyl-5alpha-cholesta-8,24-dien-3-one
• 英文别名: (4S,5S,10S,13R,14R,17R)-4,10,13-trimethyl-17-[(2R)-6-methylhept-5-en-2-yl]-1,2,4,5,6,7,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
• CAS: 7377-73-3
• 化学式: C₂₈H₄₄O
• 分子量: 396.6
• InChiKey: DBPZYKHQDWKORQ-SINUOACOSA-N

物化性质

• 沸点：
  488.1±44.0 °C(Predicted)
• 密度：
  0.99±0.1 g/cm3(Predicted)
• 物理描述：
  Solid

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4alpha-Methyl-5alpha-cholesta-8,24-dien-3-one 、 氢(+1)阳离子 、 NADPH(4-) 生成 (4alpha,5alpha,10Xi,13Xi,14Xi,17Xi,20Xi)-4-甲基胆甾-8,24-二烯-3-醇 、 NADP⁺
  参考文献：
  名称：

  哺乳动物胆固醇生物合成途径的全面机器可读视图。

  摘要：

  胆固醇生物合成是健康和疾病中众多生物过程的中心代谢中心。现有文献中缺乏对胆固醇通路如何构建以及它如何与其他通路系统相互作用的详细、综合的单一视图描述。在这里，我们对现有文献进行了系统回顾，并提供了详细的途径图，描述了胆固醇生物合成途径（甲羟戊酸、Kandutch-Russell 和 Bloch 途径）和导致 24(S),25-环氧胆固醇合成的分流途径. 该图是使用系统生物学图形符号 (SBGN) 生成的，并以 SBGN-ML 格式提供，这是一种人类可读且机器语义可解析的开放社区文件格式。

  DOI：

  10.1016/j.bcp.2013.03.021
• 作为产物：
  描述：

  4beta-Carboxy-4alpha-methyl-5alpha-cholesta-8,24-dien-3beta-ol 、 nicotinamide adenine dinucleotide 生成 4alpha-Methyl-5alpha-cholesta-8,24-dien-3-one 、 二氧化碳 、 NADH
  参考文献：
  名称：

  C-4固醇脱甲基酶区分细菌和真核固醇的合成[微生物学]

  摘要：

  甾醇是多种生理作用所必需的真核生物脂质。固醇脂质，甾烷烃的成岩产物保存在古代沉积岩中，并用作地质生物标志物，表明在整个地球历史上都存在真核生物和有氧环境。但是，也已知有几种细菌会产生固醇，这使细菌固醇合成对我们解释甾烷生物标志物的重要性产生了疑问。最近的研究表明细菌固醇的合成可能不同于真核生物中观察到的。特别地，对产生甾醇的细菌的系统生物学分析未能鉴定出几种关键的真核固醇合成酶的同源物，最显着的是在C-4位上去甲基化所需要的那些。甲基球菌荚膜其编码固醇脱甲基酶蛋白质（SDM）。我们显示，Rieske型加氧酶（SdmA）和NAD（P）依赖还原酶（SdmB）负责将4，4-二甲基固醇转化为4α-甲基固醇。鉴定SdmA-SdmB与13异源表达过程中合成的中间产物C标记研究支持不同于真核生物的固醇C-4脱甲基机制。SdmA-SdmB同源物已在其他几个产生甾醇的细菌基因组中鉴定出，但在任何真核生物基因

  DOI：

  10.1073/pnas.1802930115

文献信息

• Divergent interactions involving the oxidosqualene cyclase and the steroid-3-ketoreductase in the sterol biosynthetic pathway of mammals and yeasts
  作者：Silvia Taramino、Brian Teske、Simonetta Oliaro-Bosso、Martin Bard、Gianni Balliano

  DOI：10.1016/j.bbalip.2010.07.006

  日期：2010.11

  In mammals and yeasts, oxidosqualene cyclase (OSC) catalyzes the formation of lanosterol, the first cyclic intermediate in sterol biosynthesis. We used a murine myeloma cell line (NS0), deficient in the 17 beta-hydroxysteroid dehydrogenase type 7 (HSD17B7), as a model to study the potential interaction of the HSD17B7 with the OSC in mammals. HSD17B7 is the orthologue of the yeast steroid-3-ketoreductase (ERG27), an enzyme of ergosterol biosynthesis that plays a protective role towards OSC. Tracer experiments with NS0 cells showed that OSC is fully active in these mammalian cells, suggesting that in mammals the ketosteroid reductase is not required for OSC activity. Mouse and human HSD17B7 were overexpressed in ERG27-deletant yeast cells, and recombinant strains were tested for (i) the ability to grow on different media, (ii) steroid-3-ketoreductase activity, and (iii) OSC activity. Recombinant strains grew more slowly than the control yeast ERG27-overexpressing strain on sterol-deficient media, whereas the growth rate was normal on media supplemented with a 3-ketoreductase substrate. The full enzymatic functionality of mammalian steroid-3-ketoreductase expressed in yeast along with the lack of (yeast) OSC activity point to an inability of the mammalian reductase to assist yeast OSC. Results demonstrate that in mammals, unlike in yeast, OSC and steroid-3-ketoreductase are non-interacting proteins. (C) 2010 Elsevier B.V. All rights reserved.
• COMPOSITIONS AND METHODS FOR METABOLIC SELECTION OF TRANSFECTED CELLS
  申请人：Biofactura, Inc

  公开号：EP1910421A2

  公开（公告）日：2008-04-16
• NITROXIDES FOR USE IN TREATING OR PREVENTING HYPERCHOLESTEROLEMIA
  申请人：Mitos Pharmaceuticals, Inc

  公开号：EP2121599A2

  公开（公告）日：2009-11-25
• Compositions and Methods for Metabolic Selection of Transfected Cells
  申请人：Branco Luis

  公开号：US20100028940A1

  公开（公告）日：2010-02-04

  The present invention relates to novel selection marker vectors, and methods for using these vectors to generate stable gene expression systems in eukaryotic cells utilizing any enzyme useful in the eukaryotic sterol/cholesterol biosynthetic pathway, such as a 3-ketosteroid reductase, as a metabolic selection marker to select transfected cells. In one embodiment, the method comprises transfecting cells that are auxotrophic for cholesterol with a vector encoding 3-ketosteroid reductase and at least one heterologous protein, and selecting cells that have the ability to survive in medium lacking cholesterol and/or producing the heterologous protein in these cells in chemically defined and/or serum-free media.
• US8076102B2
  申请人：——

  公开号：US8076102B2

  公开（公告）日：2011-12-13