(25ξ)-26-hydroxycholest-4-en-3-one | 19257-21-7

• 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: (25ξ)-26-hydroxycholest-4-en-3-one
• 英文别名: 26-hydroxycholest-4-en-3-one；27-hydroxycholest-4-en-3-one；cholest-4-ene-26-ol-3-one；(8S,9S,10R,13R,14S,17R)-17-[(2R)-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: 19257-21-7
• 化学式: C₂₇H₄₄O₂
• 分子量: 400.645
• InChiKey: CXUORUGFOXGJNY-XVENTEFESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  29
• 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：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (25ξ)-26-hydroxycholest-4-en-3-one 在 吡啶 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 水 、 [双(三氟乙酰氧基)碘]苯 、 zinc(II) iodide 作用下， 以 乙醇 、 氯仿 、 二甲基亚砜 为溶剂， 反应 97.17h， 生成 4-胆甾烯-3-酮
  参考文献：
  名称：

  Rabinowitz, Michael H.; Djerassi, Carl, Journal of the American Chemical Society, 1992, vol. 114, # 1, p. 304 - 317

  摘要：

  DOI：
• 作为产物：
  描述：

  4-胆甾烯-3-酮 在 glucose-6-phosphate dehydrogenase 、 glucose 6-phosphate 、 ferredoxin 、 magnesium chloride 、 bovine liver catalase 作用下， 生成 (25ξ)-26-hydroxycholest-4-en-3-one
  参考文献：
  名称：

  细胞色素 P450 铁-过氧阴离子的近端配体电子捐赠和反应性

  摘要：

  来自结核分枝杆菌的 CYP125 催化胆固醇侧链末端甲基的顺序氧化为醇、醛，最后为酸。在这里，我们证明 CYP125 同时催化五种其他产物的形成，所有这些产物都是由甾醇侧链的去甲酰化引起的。醛中间体显示为常规酸代谢物和五种去甲酰化产物的前体。酸通过三价铁-过氧阴离子物质的质子化和铁氧化物物质（也称为化合物 I）的形成而产生，然后是夺氢和氧转移。通过向醛中间体添加相同的铁-过氧阴离子以产生导致 CC 键断裂的过氧半缩醛，产生去甲酰化产物。催化序列的这种分叉使我们能够检查近端配体的电子捐赠对过氧化铁阴离子性质的影响。用硒代半胱氨酸替换半胱氨酸硫醇铁配体导致 UV-vis、EPR 和共振拉曼光谱变化，表明从近端硒酸配体到铁的电子捐赠增加。对硒代半胱氨酸取代酶反应中产物分布的分析揭示了酸的形成（化合物 I 途径）以去甲酰化产物为代价。这些观察结果与过氧化铁阴离子 pK(a) 的增加一致，这有利于其质子化，因此有利于化合物

  DOI：

  10.1021/ja211499q

文献信息

• Structural and Biochemical Characterization of Mycobacterium tuberculosis CYP142
  作者：Max D. Driscoll、Kirsty J. McLean、Colin Levy、Natalia Mast、Irina A. Pikuleva、Pierre Lafite、Stephen E.J. Rigby、David Leys、Andrew W. Munro

  DOI：10.1074/jbc.m110.164293

  日期：2010.12

  M. tuberculosis CYP125, but having a near-identical organization of distal pocket residues to the branched fatty acid oxidizing M. tuberculosis CYP124. The cholesterol oxidizing activity of CYP142 provides an explanation for previous findings that DeltaCYP125 strains of Mycobacterium bovis and M. bovis BCG cannot grow on cholesterol, because these strains have a defective CYP142 gene. CYP142 is revealed

  结核分枝杆菌细胞色素 P450 酶 CYP142 由参与宿主胆固醇代谢的大型基因簇编码。 CYP142 被表达并纯化为可溶性低自旋 P450 血红素蛋白。 CYP142 与胆固醇及其氧化衍生物 cholest-4-en-3-one 紧密结合，使血红素铁广泛转变为高自旋状态。证明了对唑类抗生素的高亲和力，突出了它们的治疗潜力。 CYP142 催化胆固醇/cholest-4-en-3-one 的 27-羟基化，或通过连续的甾醇氧化从这些底物生成 5-胆烯酸/cholestenic-en-3-one-27-oic 酸，催化结果取决于所使用的氧化还原伙伴系统。 CYP142晶体结构解析为1.6 A，揭示了与胆固醇代谢结核分枝杆菌CYP125相似的活性位点组织，但具有与支链脂肪酸氧化结核分枝杆菌CYP124几乎相同的远端口袋残基组织。 CYP142 的胆固醇氧化活性为之前的发现提供了解释，即牛分枝杆菌和牛分枝杆菌
• [EN] COMPETITIVE IMMUNOASSAY METHODS<br/>[FR] PROCÉDÉS DE DOSAGE IMMUNOLOGIQUE PAR COMPÉTITION
  申请人：NESTEC SA

  公开号：WO2018011691A1

  公开（公告）日：2018-01-18

  The invention provides assay methods and kits for detecting, measuring or quantitating the level of 7α-hydroxy-4-cholesten-3-one (7C4) in a biological sample from a subject, such as a human subject. In some embodiments, the human subject has a condition associated with bile acid malabsorption or diarrhea of unknown origin. The invention also provides isolated antibodies or antibody fragment thereof that specifically binds to 7α- hydroxy-4-cholesten-3-one (7C4) and have less than 1% cross-reactivity to one or more members selected from the group consisting of 7-ketocholesterol, 7α-hydroxycholesterol, and trihydroxycholestanoic acid.

  本发明提供了检测、测量或定量生物样本中7α-羟基-4-胆甾烯-3-酮（7C4）水平的测定方法和试剂盒，所述生物样本来自于受试者，例如人类受试者。在某些实施方式中，人类受试者患有与胆酸吸收不良或不明原因腹泻相关的疾病。本发明还提供了特异性结合于7α-羟基-4-胆甾烯-3-酮（7C4）并且与7-酮胆固醇、7α-羟基胆固醇和三羟基胆甾酸中的一个或多个成员的交叉反应小于1％的分离抗体或抗体片段。
• LIGANDS FOR NEMATODE NUCLEAR RECEPTORS AND USES THEREOF
  申请人：Mangelsdorf J. David

  公开号：US20070219173A1

  公开（公告）日：2007-09-20

  Anti-nematode compounds, compositions, and methods for identifying such compounds are disclosed, where the compounds have the formula I: where Q, Q′, R 1 , R 2 , and n are defined herein.

  本文披露了抗线虫化合物、组合物以及鉴定这种化合物的方法，其中化合物的公式为I：其中Q、Q'、R1、R2和n的定义如本文所述。
• Ligands for nematode nuclear receptors and uses thereof
  申请人：Board of Regents, University of Texas System

  公开号：US10117878B2

  公开（公告）日：2018-11-06

  An effective anti-nematode methodology entails contacting nematodes with a biologically effective amount of at least one compound according to formula I: where Q, Q′, R1, R2, and n are defined herein, or with a stereoisomer, solvate, or pharmaceutically acceptable salt of such compound.

  有效的抗线虫方法需要将线虫与生物有效量的至少一种根据式 I 的化合物接触： 其中 Q、Q′、R1、R2 和 n 在本文中定义，或与该化合物的立体异构体、溶液或药学上可接受的盐接触。
• Synthesis of potential C27-intermediates in bile acid biosynthesis and their deuterium-labeled analogs
  作者：Junichi Shoda、Magnus Axelson、Jan Sjövall

  DOI：10.1016/0039-128x(93)90048-r

  日期：1993.3

  In connection with studies of alternative pathways in bile acid biosynthesis, potential intermediates in a pathway starting with 27-hydroxylation of cholesterol have been prepared in natural and deuterated forms. Established methods were used to prepare 27-hydroxycholesterol and 3beta-hydroxy-5-cholestenoic acid. Clemmensen reduction of kryptogenin in unlabeled and deuterated solvents yielded 27-hydroxy-cholesterol and 16-oxo-5-cholestene-3beta,27-diol, which were separated by adsorption chromatography on Unisil. The labeled 27-hydroxycholesterol and 3beta-hydroxy-5-cholestenoic acid derived from it consisted of molecules with seven (50%), six (20%), and eight (20%) deuterium atoms, and unlabeled molecules were not detected. The acetates of 27-hydroxycholesterol and methyl 3beta-hydroxy-5-cholestenoate were 7alpha-hydroxylated in a copper-catalyzed reaction with tert-butylperbenzoate, and the products were purified by chromatography on Unisil. The 7beta-epimers were obtained as side products. Labeled 3beta,7alpha-dihydroxy-5-cholenoic acid was prepared in the same way from 3beta-hydroxy-5-[2,2,4,4,23-H-2(5)-cholenoic acid. The 3-oxo-DELTA4 analogs of the 3beta-hydroxy-DELTA5 compounds were prepared by oxidation with cholesterol oxidase. The labeled products had the same isotopic composition as the starting materials. Gas chromatographic retention indices and mass spectral characteristics of the trimethylsilyl ether derivatives of the neutral steroid and the methylated acids are given for all compounds.