4α-methylcholest-7-en-3-one | 2789-43-7

• 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: 4α-methylcholest-7-en-3-one
• 英文别名: cholest-4α-methyl-7-en-3β-one；4α-methyl-5α-cholest-7-en-3-one；Lophenon；4α-Methyl-5α-cholest-7-en-3-on；lophenone；4alpha-Methyl-5alpha-cholest-7-en-3-one；(4S,5S,9R,10S,13R,14R,17R)-4,10,13-trimethyl-17-[(2R)-6-methylheptan-2-yl]-1,2,4,5,6,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
• CAS: 2789-43-7
• 化学式: C₂₈H₄₆O
• 分子量: 398.673
• InChiKey: OWKGVPXWOHLTSL-LIUJFMQASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.4
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.89
• 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：

  4α-methylcholest-7-en-3-one 在 platinum(IV) oxide 氢气 作用下， 以 溶剂黄146 为溶剂， 生成 4alpha-甲基-5alpha-胆甾-8(14)-烯-3beta-醇
  参考文献：
  名称：

  Novel nuclear methylation of sterols by the nematode caenorhabditis elegans

  摘要：

  Caenorhabditis elegans possesses a unique sterol methylation pathway not reported to occur in any other organism and also removes the C-24 ethyl group of sitosterol (a plant sterol). This nematode produced substantial quantities of 4 alpha-methyl-5 alpha-cholest-8(14)-en-3 beta-ol and smaller amounts of lophenol from dietary cholesterol, desmosterol or sitosterol. When C. elegans was propagated in media containing sitosterol plus 25-azacoprostane hydrochloride (25-aza-5 beta-cholestane hydrochloride), an inhibitor of delta 24-sterol reductase in insects, its 4 alpha-methylsterol fraction largely consisted of equal amounts of 4 alpha-methyl-5 alpha-cholesta-7,24-dien-3 beta-ol and 4 alpha-methyl-5 alpha-cholesta-8(14),24-dien-3 beta-ol. Thus 25-azacoprostane hydrochloride inhibited both a delta 24-sterol reductase and a delta 7-sterol isomerase in C. elegans.

  DOI：

  10.1016/0039-128x(83)90042-9
• 作为产物：
  描述：

  4-甲基胆甾-7-烯-3-醇 在 吡啶 、 chromium(VI) oxide 作用下， 生成 4α-methylcholest-7-en-3-one
  参考文献：
  名称：

  Pyrek,J.S.; Schmidt-Szalowska,A., Roczniki Chemii, 1977, vol. 51, p. 951 - 958

  摘要：

  DOI：

文献信息

• Metabolism of 27-nor-24,25-dihydrolanosterol and 23,24,25,26,27-pentanor-dihydrolanosterol by rat liver hommogenate preparations.
  作者：YOSHIHIRO SATO、YOSHIKO SONODA

  DOI：10.1248/cpb.30.628

  日期：——

  The metabolism of 27-nor-24, 25-dihydrolanosterol (1) which is an effective inhibitor of cholesterol biosynthesis from lanosterol was studied using the unlabeled and 24, 25-tritiated compounds. 1 was transformed into the cholesterol analog, 27-norcholesterol, to the extent of 6.5% by incubation with rat liver homogenate under conditions such that lanosterol in the control experiment was converted to cholesterol to the extent of 24.8%. The structures of two other metabolites (9 and 11) were determined. On the other hand, 23, 24, 25, 26, 27-pentanordihydrolanosterol (2), which is also an inhibitor, was not transformed into the corresponding cholesterol analog, suggesting the importance of the side chain structure of lanosterol in cholesterol biosynthesis.

  研究了27-去甲-24, 25-二氢兰斯特醇（1）的代谢，该化合物是从兰斯特醇合成胆固醇的有效抑制剂，使用了未标记和24, 25-氚标记的化合物。1在与大鼠肝脏匀浆孵育的条件下，转化为胆固醇类似物27-去胆固醇的程度为6.5%，而对照实验中兰斯特醇转化为胆固醇的程度为24.8%。另外两个代谢产物（9和11）的结构也被确定。另一方面，23, 24, 25, 26, 27-戊去二氢兰斯特醇（2）作为抑制剂，并未转化为相应的胆固醇类似物，这表明兰斯特醇的侧链结构在胆固醇生物合成中的重要性。
• Characterization of the <i>Saccharomyces cerevisiae ERG27</i> gene encoding the 3-keto reductase involved in C-4 sterol demethylation
  作者：D. Gachotte、S. E. Sen、J. Eckstein、R. Barbuch、M. Krieger、B. D. Ray、M. Bard

  DOI：10.1073/pnas.96.22.12655

  日期：1999.10.26

  the 3-keto sterol reductase, which, in concert with the C-4 sterol methyloxidase (ERG25) and the C-3 sterol dehydrogenase (ERG26), catalyzes the sequential removal of the two methyl groups at the sterol C-4 position. We developed a strategy to isolate a mutant deficient in converting 3-keto to 3-hydroxy-sterols. An ergosterol auxotroph unable to synthesize sterol or grow without sterol supplementation

  已经克隆了编码酿酒酵母中麦角甾醇生物合成中涉及的酶的最后一个未鉴定基因。这个称为ERG27的基因编码3-酮固醇还原酶，与C-4固醇甲基氧化酶（ERG25）和C-3固醇脱氢酶（ERG26）协同作用，催化顺序去除两个甲基固醇C-4的位置。我们开发了一种策略来分离将3-酮转化为3-羟基固醇不足的突变体。诱变了不能合成固醇或不能在不添加固醇的情况下生长的麦角固醇营养缺陷型。然后选择在3-酮麦角二烯和胆固醇存在下耐制霉菌素的菌落。分离出一种新的麦角固醇营养缺陷型，在不添加胆固醇的情况下不能在3-酮固醇上生长。通过互补鉴定了基因（YLR100w）。含有YLR100w干扰的分离剂无法在各种类型的3-酮固醇底物上生长。出乎意料的是，当erg27在补充了胆固醇或麦角固醇的培养基上生长时，所积累的内源性化合物是非环状固醇中间体（角鲨烯，角鲨烯环氧和角鲨烯二氧化物），而羊毛甾醇或3-酮固醇几乎没有或没有积累。在
• Closing the Gap: Identification of Human 3-Ketosteroid Reductase, the Last Unknown Enzyme of Mammalian Cholesterol Biosynthesis
  作者：Zrinka Marijanovic、Daniela Laubner、Gabriele Möller、Christian Gege、Bettina Husen、Jerzy Adamski、Rainer Breitling

  DOI：10.1210/me.2002-0436

  日期：2003.9

  cholesterol-deficiency disorders. We conclude that HSD17B7 participates in postsqualene cholesterol biosynthesis, thus completing the molecular cloning of all genes of this central metabolic pathway. In its function as the 3-ketosteroid reductase of cholesterol biosynthesis, HSD17B7 is a novel candidate for inborn errors of cholesterol metabolism.

  由HSD17B7基因编码的蛋白质最初被描述为催乳激素受体相关的蛋白质和17β-羟类固醇脱氢酶（HSD）7型。先前已报道了其在体外合成17β-雌二醇的能力。然而，我们证明了HSD17B7是酵母3-酮类固醇还原酶Erg27p的直系同源物，并在体外使用还原的烟酰胺腺嘌呤二核苷酸磷酸作为辅因子将zymosterone转换为zymosterol。人和鼠类HSD17B7在缺乏Erg27p的酵母菌株中的表达可补充细胞的3-酮类固醇还原酶缺乏症，并在缺乏甾醇的培养基上恢复生长。HSD17B7与绿色荧光蛋白的融合体位于内质网，即角鲨烯胆甾醇生成后的位置。HSD17B7在胆固醇代谢中的作用的进一步关键证据是，其观察到的鼠直向同源物与羟甲基-戊二酰辅酶A还原酶，固醇生物发生的限速酶和在先天性胆固醇缺乏症的发病机理中涉及的组织中特异性表达“α-淀粉样蛋白”。我们得出的结论是，HSD17B7参与角鲨烯后胆固醇的生物
• The Neutral Constituents of the Cactus Lophocereus schottii. The Structure of Lophenol--4α-Methyl-Δ⁷-cholesten-3β-ol--A Link in Sterol Biogenesis^1-3
  作者：Carl Djerassi、G. W. Krakower、A. J. Lemin、Liang H. Liu、J. S. Mills、R. Villotti

  DOI：10.1021/ja01556a031

  日期：1958.12
• Synthesis of 4α-Methyl-Δ⁷-steroiäs. The Interrelationship of Cholesterol, Citrostadienol and Lophenol
  作者：Yehuda Mazur、Franz Sondheimer

  DOI：10.1021/ja01556a033

  日期：1958.12