(25R)-7α,26-dihydroxycholest-4-en-3-one | 192187-67-0

• 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: (25R)-7α,26-dihydroxycholest-4-en-3-one
• 英文别名: (25R)-7alpha,26-dihydroxycholest-4-en-3-one；(7R,8S,9S,10R,13R,14S,17R)-7-hydroxy-17-[(2R,6R)-7-hydroxy-6-methylheptan-2-yl]-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
• CAS: 192187-67-0
• 化学式: C₂₇H₄₄O₃
• 分子量: 416.645
• InChiKey: KVJVJJWIEXCECB-OICBIKJFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 (25R)-7α,26-dihydroxycholest-4-en-3-one 在 吡啶 作用下， 以71%的产率得到Acetic acid (2R,6R)-6-((7R,8S,9S,10R,13R,14S,17R)-7-hydroxy-10,13-dimethyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-2-methyl-heptyl ester
  参考文献：
  名称：

  两种海洋天然产物的合成：pavoninin-1和2的糖苷配基

  摘要：

  pavoninin-1和2的糖苷配基的首次合成已通过环氧化物12完成。

  DOI：

  10.1016/s0040-4020(97)00497-3
• 作为产物：
  描述：

  (25R)-26-(tert-butyldimethylsilyloxy)cholest-5-en-3β-ol 在 RhCl(PPh₃)3 吡啶 、 盐酸 、 manganese(IV) oxide 、 lithium aluminium tetrahydride 、 氢气 、 环己酮 、 aluminum isopropoxide 、 对甲苯磺酸 、 间氯过氧苯甲酸 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醇 、 二氯甲烷 、 丙酮 、 甲苯 为溶剂， 反应 156.5h， 生成 (25R)-7α,26-dihydroxycholest-4-en-3-one
  参考文献：
  名称：

  两种海洋天然产物的合成：pavoninin-1和2的糖苷配基

  摘要：

  pavoninin-1和2的糖苷配基的首次合成已通过环氧化物12完成。

  DOI：

  10.1016/s0040-4020(97)00497-3

文献信息

• Sterol synthesis. Preparation and characterization of fluorinated and deuterated analogs of oxygenated derivatives of cholesterol
  作者：Shengrong Li、Jihai Pang、William K. Wilson、George J. Schroepfer, Jr.

  DOI：10.1016/s0009-3084(99)00005-5

  日期：1999.5

  preparation, purification and characterization of 43 oxygenated sterols, including the 4 beta-hydroxy, 7 alpha-hydroxy, 7 beta-hydroxy, 7-keto, and 19-hydroxy derivatives of cholesterol and their analogs with 25,26,26,26,27,27,27-heptafluoro (F7) and 26,26,26,27,27,27-hexadeuterio (d6) substitution. The 7 alpha-hydroxy, 7 beta-hydroxy, and 7-keto derivatives of (25R)-cholest-5-ene-3 beta, 26-diol (1d) and their

  氧化的固醇，包括自氧化产物和固醇代谢产物，都具有许多重要的生物学活性。可靠标准品的提供大大简化了通过色谱和光谱法鉴定和定量氧固醇的方法，氘代和氟化类似物作为定量内标非常有价值。我们描述了43种含氧固醇的制备，纯化和表征，包括胆固醇及其类似物与25,26,26的4β-羟基，7α-羟基，7β-羟基，7-酮和19-羟基衍生物，26,27,27,27-七氟（F7）和26,26,26,27,27,27-六氘（d6）取代。还制备了（25R）-胆甾-5-烯-3β，26-二醇（1d）的7α-羟基，7β-羟基和7-酮衍生物及其16,16-二氘代子宫类似物。这些d2-26-羟基甾醇和[16,16-2H2]-（25R）-胆甾烯-5 -ene-3β，26-二醇（1e）是由[16,16-2H2]-（25R）-胆甾醇合成的可以由薯os皂苷元制备-5-烯-3β，26-二醇二乙酸酯（2e）。1e和2e中C-16处高度特异
• The bile acid synthetic gene 3β-hydroxy-Δ5-C27-steroid oxidoreductase is mutated in progressive intrahepatic cholestasis
  作者：Margrit Schwarz、Angelique C. Wright、Daphne L. Davis、Hisham Nazer、Ingemar Björkhem、David W. Russell

  DOI：10.1172/jci10902

  日期：2000.11.1

  We used expression cloning to isolate cDNAs encoding a microsomal 3 beta -hydroxy-Delta (5)-C-27-steroid oxidoreductase (C-27 3 beta -HSD) that is expressed predominantly in the liver. The predicted product shares 34% sequence identity with the C-19 and C-21 3 beta -HSD enzymes, which participate in steroid hormone metabolism. When transfected into cultured cells, the cloned C-27 3 beta -HSD cDNA encodes an enzyme that is active against four 7 alpha -hydroxylated sterols, indicating that a single C-27 3 beta -HSD enzyme can participate in all known pathways of bile acid synthesis. The expressed enzyme did not metabolize several different C-19/21 steroids as substrates. The levels of hepatic C-27 3 beta -HSD mRNA in the mouse are not sexually dimorphic and do not change in response to dietary cholesterol or to changes in bile acid pool size. The corresponding human gene on chromosome 16p11.2-12 contains six exons and spans 3 kb of DNA, and we identified a 2-bp deletion in the C-27 3 beta -HSD gene of a patient with neonatal progressive intrahepatic cholestasis. This mutation eliminates the activity of the enzyme in transfected cells. These findings establish the central role of C-27 3 beta -HSD in the biosynthesis of bile acids and provide molecular tools for the diagnosis of a third type of neonatal progressive intrahepatic cholestasis associated with impaired bile acid synthesis.