cholest-4-en-3-one-27-oic acid | 23017-97-2

• 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: cholest-4-en-3-one-27-oic acid
• 英文别名: 3-keto-4-cholestene-27-oic acid；Delta(4)-dafachronic acid；(6R)-6-[(8S,9S,10R,13R,14S,17R)-10,13-dimethyl-3-oxo-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl]-2-methylheptanoic acid
• CAS: 23017-97-2
• 化学式: C₂₇H₄₂O₃
• 分子量: 414.629
• InChiKey: PSXQJZDFWDKBIP-NNWQCNCGSA-N

物化性质

• 沸点：
  554.6±19.0 °C(Predicted)
• 密度：
  1.07±0.1 g/cm3(Predicted)
• 溶解度：
  DMF：5mg/mL； DMSO：2.5mg/mL；乙醇：12.5mg/mL；乙醇:PBS (pH 7.2) (1:10): 0.09 mg/mL

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.85
• 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：

  4-胆甾烯-3-酮 在 glucose-6-phosphate dehydrogenase 、 D-葡萄糖-6-磷酸 、 spinach ferredoxin reductase 、 recombinant Mycobacterium tuberculosis cytochrome P₄₅₀ enzyme CYP₁₄₂ 、 还原型辅酶II(NADPH)四钠盐 、 spinach ferredoxin 作用下， 反应 0.5h， 生成 cholest-4-en-3-one-27-oic acid
  参考文献：
  名称：

  结核分枝杆菌 CYP142 的结构和生化特征：人类病原体中多种胆固醇 27-羟化酶活性的证据。

  摘要：

  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

  DOI：

  10.1074/jbc.m110.164293

文献信息

• 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。
• Compound and method for the treatment and diagnosis of neurodegenerative conditions
  申请人：SWANSEA UNIVERSITY

  公开号：US10226475B2

  公开（公告）日：2019-03-12

  A reagent selected from cholestenoic acid or an inhibitor of an enzyme in the cholestenoic acid biosynthetic or metabolic pathway for use in the treatment of neurodegenerative conditions. In particular, the reagent is a cholestenoic acid of a particular form, such as 3β,7α-dihydroxycholest-5-en-26-oic (3β,7α-diHCA), not previously associated with neural tissue or CSF. Pharmaceutical compositions, methods of treatment or prevention of neurodegenerative conditions as well as diagnostic methods and novel biomarkers form further aspects of the invention.

  一种选自胆烯酸或胆烯酸生物合成或代谢途径中酶的抑制剂的试剂，用于治疗神经退行性疾病。特别是，该试剂是一种特殊形式的胆甾烯酸，如 3β,7α-二羟基胆甾烯-5-烯-26-酸（3β,7α-diHCA），以前与神经组织或 CSF 无关。本发明还包括药物组合物、治疗或预防神经退行性疾病的方法以及诊断方法和新型生物标记物。
• 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.
• CYTOSTATIC STEROLS
  申请人：MEDIVIR AB

  公开号：EP0906331A1

  公开（公告）日：1999-04-07