7α,25-dihydroxy-4-cholesten-3-one | 98774-41-5

• 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: 7α,25-dihydroxy-4-cholesten-3-one
• 英文别名: 7alpha,25-Dihydroxy-4-cholesten-3-one；(7R,8S,9S,10R,13R,14S,17R)-7-hydroxy-17-[(2R)-6-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: 98774-41-5
• 化学式: C₂₇H₄₄O₃
• 分子量: 416.645
• InChiKey: POUKDTOWHPHYQU-HENOKILYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  30
• 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：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-氯-N-吡啶基乙酰肼 、 7α,25-dihydroxy-4-cholesten-3-one 以 甲醇 、 水 、 溶剂黄146 为溶剂， 生成
  参考文献：
  名称：

  Analysis of derivatised steroids by matrix-assisted laser desorption/ionisation and post-source decay mass spectrometry

  摘要：

  Neutral steroids are difficult to analyse using desorption ionisation methods coupled with mass spectrometry (MS). However, steroids with an unhindered ketone group can readily be derivatised with the Girard P (GP) reagent to give GP hydrazones. Steroid GP hydrazones contain a quaternary nitrogen atom and are readily desorbed in the matrix-assisted laser desorption/ionisation (MALDI) process, giving an improvement in sensitivity of two orders of magnitude. Steroids without a ketone group, but with a 3 beta-hydroxy-Delta(5) function, can be readily converted to 3-OXO-Delta(4) steroids and subsequently derivatised to GP hydrazones for MALDI analysis. In addition to giving strong [M](+) ions upon MALDI, steroid GP hydrazones give informative post-source decay (PSD) spectra. By using the accurate mass of the precursor-ion measured by MALDI-MS, in combination with the structural information encoded in its PSD spectrum, steroid structures can readily be determined. (c) 2005 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2005.08.002
• 作为产物：
  描述：

  7α,25-二羟基胆固醇 在 recombinant Brevibacterium cholesterol oxidase 作用下， 以 phosphate buffer 、 异丙醇 为溶剂， 反应 12.0h， 生成 7α,25-dihydroxy-4-cholesten-3-one
  参考文献：
  名称：

  Analysis of derivatised steroids by matrix-assisted laser desorption/ionisation and post-source decay mass spectrometry

  摘要：

  Neutral steroids are difficult to analyse using desorption ionisation methods coupled with mass spectrometry (MS). However, steroids with an unhindered ketone group can readily be derivatised with the Girard P (GP) reagent to give GP hydrazones. Steroid GP hydrazones contain a quaternary nitrogen atom and are readily desorbed in the matrix-assisted laser desorption/ionisation (MALDI) process, giving an improvement in sensitivity of two orders of magnitude. Steroids without a ketone group, but with a 3 beta-hydroxy-Delta(5) function, can be readily converted to 3-OXO-Delta(4) steroids and subsequently derivatised to GP hydrazones for MALDI analysis. In addition to giving strong [M](+) ions upon MALDI, steroid GP hydrazones give informative post-source decay (PSD) spectra. By using the accurate mass of the precursor-ion measured by MALDI-MS, in combination with the structural information encoded in its PSD spectrum, steroid structures can readily be determined. (c) 2005 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2005.08.002

文献信息

• Molecular Genetics of 3β-Hydroxy-Δ5-C27-Steroid Oxidoreductase Deficiency in 16 Patients with Loss of Bile Acid Synthesis and Liver Disease
  作者：Jeffrey B. Cheng、Emmanuel Jacquemin、Marie Gerhardt、Hisham Nazer、Danièle Cresteil、James E. Heubi、Kenneth D. R. Setchell、David W. Russell

  DOI：10.1210/jc.2002-021580

  日期：2003.4.1

  The 3β-hydroxy-Δ5-C27-steroid oxidoreductase (C27 3β-HSD) is a membrane-bound enzyme of the endoplasmic reticulum that catalyzes an early step in the synthesis of bile acids from cholesterol. Subjects with autosomal recessive mutations in the encoding gene, HSD3B7, on chromosome 16p11.2–12 fail to synthesize bile acids and develop a form of progressive liver disease characterized by cholestatic jaundice and malabsorption of lipids and lipid-soluble vitamins from the gastrointestinal tract. The gene encoding the human C27 3β-HSD enzyme was isolated previously, and a 2-bp deletion in exon 6 of HSD3B7 was identified in a well characterized subject with this disorder. Here, we report a molecular analysis of 15 additional patients from 13 kindreds with C27 3β-HSD deficiency. Twelve different mutations were identified in the HSD3B7 gene on chromosome 16p11.2–12. Ten mutations were studied in detail and shown to cause complete loss of enzyme activity and, in two cases, alterations in the size or amount of the transcribed mRNA. Mutations were inherited in homozygous form in 13 subjects from 10 families and compound heterozygous form in four subjects from three families. We conclude that a diverse spectrum of mutations in the HSD3B7 gene underlies this rare form of neonatal cholestasis.

  3β-羟基-Δ5-C27类固醇氧化还原酶（C27 3β-HSD）是内质网的膜结合酶，催化从胆固醇合成胆汁酸的早期步骤。携带在16p11.2-12染色体上的编码基因HSD3B7发生常染色体隐性突变的个体无法合成胆汁酸，发展出一种以胆汁淤积性黄疸和脂肪和脂溶性维生素从胃肠道吸收不良为特征的进行性肝病。人类C27 3β-HSD酶的编码基因已被分离出来，并在一个已知患者的第6外显子中鉴定出2个碱基的缺失。在这里，我们报告了对13个家族的15名C27 3β-HSD缺陷患者的分子分析。在16p11.2-12染色体上的HSD3B7基因中鉴定出12个不同的突变。对10个突变进行了详细研究，证明它们能够完全失去酶活性，并且在两种情况下改变了转录的mRNA的大小或数量。在10个家族的13名患者中以纯合形式遗传突变，在3个家族的4名患者中以复合杂合形式遗传突变。我们得出结论，HSD3B7基因的多样突变谱系是这种罕见的新生儿胆汁淤积症的基础。
• 細胞分裂阻止性ステロール
  申请人：——

  公开号：JP2000512626A

  公开（公告）日：2000-09-26

  \n (57)【要約】\n式（Ｉ）（式中、Ｘは直鎖または分岐鎖のヒドロキシ置換Ｃ1−Ｃ15炭化水素鎖である）で示される化合物は、急速に増殖する細胞および黒色腫などの癌に付随する状態の治療において有用性を有する。\n \n

  \(57) [摘要]根据式(I)（其中X是羟基取代的C1-C15烃链的直链或支链）的化合物在治疗快速增殖的细胞和与癌症有关的病症（如黑色素瘤）方面具有实用价值。\n \n
• 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。
• Methods for diagnosing motor neuron diseases
  申请人：SWANSEA UNIVERSITY

  公开号：US11536730B2

  公开（公告）日：2022-12-27

  The invention relates to methods for determining whether a subject is afflicted with a motor neuron disease, the method comprising conducting an analysis of cerebrospinal fluid and/or plasma, measuring the level of one or more sterol/oxysterol analytes, and comparing these to reference values. Further, the invention relates to methods of identifying agents suitable for the treatment of MND, and monitoring the progress of the disease.

  本发明涉及确定受试者是否患有运动神经元疾病的方法，该方法包括对脑脊液和/或血浆进行分析，测量一种或多种甾醇/氧甾醇分析物的水平，并将其与参考值进行比较。 此外，本发明还涉及鉴定适用于治疗运动神经元疾病的药物和监测疾病进展的方法。
• Bile acids. LXXIII. Synthesis of analogs of 7α-hydroxy-4-cholesten-3-one as substrates for hepatic steroid 12α-hydroxylase
  作者：M JOYCE、S HIREMATH、M MATTAMMAL、W ELLIOTT

  DOI：10.1016/s0039-128x(84)80020-3

  日期：1984.7

  Analogs of 7 alpha-hydroxy-4-cholesten-3-one were prepared to ascertain structural features necessary for maximal activity of hepatic microsomal 12 alpha-steroid hydroxylase. Methyl 3 alpha,7 alpha-dihydroxy-5 beta-cholane-24-carboxylate derived from chenodeoxycholic acid was oxidized at C-3 with silver carbonate/Celite. The product was hydrolyzed and dehydrogenated with SeO2 to provide 3-oxo-7 alpha-hydroxy-4-cholene-24-carboxylic acid. 5 beta-Cholestane-3 alpha,7 alpha,25-triol and 5 beta-cholestane-3 alpha,7 alpha,12 alpha,25-tetrol were similarly oxidized at C-3 and dehydrogenated to provide 7 alpha,25-dihydroxy-4-cholesten-3-one and 7 alpha,12 alpha,25-trihydroxy-4-cholesten-3-one, respectively. The products were characterized by thin-layer and gas chromatography, ultraviolet, infrared, proton resonance and mass spectrometry.