5α-androstan-3α,17β-diol | 33526-31-7

• 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: 5α-androstan-3α,17β-diol
• 英文别名: 3α,17β-androstandiol；3α-androstanediol；dihydroandrosterone；DHAN；androstane-3α, 17β-diol；androstane-3α,17β-diol；Androstane-3alpha,17beta-diol；(3R,8R,9S,10S,13S,14S,17S)-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3,17-diol
• CAS: 33526-31-7
• 化学式: C₁₉H₃₂O₂
• 分子量: 292.462
• InChiKey: CBMYJHIOYJEBSB-JBDJBKRMSA-N

物化性质

• 熔点：
  229 °C
• 沸点：
  415.0±18.0 °C(Predicted)
• 密度：
  1.090±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5α-androstan-3α,17β-diol 在 aldo-keto reductase 1B₁₅ (AKR₁B_15.1 isoform) 、 烟酰胺腺嘌呤双核苷酸磷酸盐 、 BSA 作用下， 生成 雄酮
  参考文献：
  名称：

  Aldo-keto Reductase 1B15 (AKR1B15)

  摘要：

  Aldo-keto reductases (AKRs) comprise a superfamily of proteins involved in the reduction and oxidation of biogenic and xenobiotic carbonyls. In humans, at least 15 AKR superfamily members have been identified so far. One of these is a newly identified gene locus, AKR1B15, which clusters on chromosome 7 with the other human AKR1B subfamily members (i.e. AKR1B1 and AKR1B10). We show that alternative splicing of the AKR1B15 gene transcript gives rise to two protein isoforms with different N termini: AKR1B15.1 is a 316-amino acid protein with 91% amino acid identity to AKR1B10; AKR1B15.2 has a prolonged N terminus and consists of 344 amino acid residues. The two gene products differ in their expression level, subcellutar localization, and activity. In contrast with other AKR enzymes, which are mostly cytosolic, AKR1B15.1 co-localizes with the mitochondria. Kinetic studies show that AKR1B15.1 is predominantly a reductive enzyme that catalyzes the reduction of androgens and estrogens with high positional selectivity (17 beta-hydroxysteroid dehydrogenase activity) as well as 3-ketoacyl-CoA conjugates and exhibits strong cofactor selectivity toward NADP(H). In accordance with its substrate spectrum, the enzyme is expressed at the highest levels in steroid-sensitive tissues, namely placenta, testis, and adipose tissue. Placental and adipose expression could be reproduced in the Be Wo and SCiBS cell lines, respectively. In contrast, AKR1 B15.2 localizes to the cytosol and displays no enzymatic activity with the substrates tested. Collectively, these results demonstrate the exis- tence of a novel catalytically active AKR, which is associated with mitochondria and expressed mainly in steroid-sensitive tissues.

  DOI：

  10.1074/jbc.m114.610121
• 作为产物：
  描述：

  雄酮 在 aldo-keto reductase 1B₁₅ (AKR₁B_15.1 isoform) 、 还原型辅酶II(NADPH)四钠盐 、 BSA 作用下， 生成 5α-androstan-3α,17β-diol
  参考文献：
  名称：

  Aldo-keto Reductase 1B15 (AKR1B15)

  摘要：

  Aldo-keto reductases (AKRs) comprise a superfamily of proteins involved in the reduction and oxidation of biogenic and xenobiotic carbonyls. In humans, at least 15 AKR superfamily members have been identified so far. One of these is a newly identified gene locus, AKR1B15, which clusters on chromosome 7 with the other human AKR1B subfamily members (i.e. AKR1B1 and AKR1B10). We show that alternative splicing of the AKR1B15 gene transcript gives rise to two protein isoforms with different N termini: AKR1B15.1 is a 316-amino acid protein with 91% amino acid identity to AKR1B10; AKR1B15.2 has a prolonged N terminus and consists of 344 amino acid residues. The two gene products differ in their expression level, subcellutar localization, and activity. In contrast with other AKR enzymes, which are mostly cytosolic, AKR1B15.1 co-localizes with the mitochondria. Kinetic studies show that AKR1B15.1 is predominantly a reductive enzyme that catalyzes the reduction of androgens and estrogens with high positional selectivity (17 beta-hydroxysteroid dehydrogenase activity) as well as 3-ketoacyl-CoA conjugates and exhibits strong cofactor selectivity toward NADP(H). In accordance with its substrate spectrum, the enzyme is expressed at the highest levels in steroid-sensitive tissues, namely placenta, testis, and adipose tissue. Placental and adipose expression could be reproduced in the Be Wo and SCiBS cell lines, respectively. In contrast, AKR1 B15.2 localizes to the cytosol and displays no enzymatic activity with the substrates tested. Collectively, these results demonstrate the exis- tence of a novel catalytically active AKR, which is associated with mitochondria and expressed mainly in steroid-sensitive tissues.

  DOI：

  10.1074/jbc.m114.610121

文献信息

• A NEW POWERFUL AND SELECTIVE REDUCING AGENT SODIUM BOROHYDRIDE-PALLADIUM CHLORIDE SYSTEM
  作者：Toshio Satoh、Naoki Mitsuo、Mayumi Nishiki、Kenryo Nanba、Shuichi Suzuki

  DOI：10.1246/cl.1981.1029

  日期：1981.7.5

  A new reducing agent, sodium borohydride-palladium chloride system reduces aryl ketones, aryl chlorides, and benzylic alcohols to corresponding hydrocarbons. It also reduces hindered steroidal ketones to alcohols in good yields.

  一种新的还原剂，硼氢化钠-氯化钯系统将芳基酮、芳基氯化物和苯甲醇还原成相应的烃。它还以良好的收率将受阻甾体酮还原为醇。
• [EN] COUMARIN-MODIFIED ANDROGENS FOR THE TREATMENT OF PROSTATE CANCER<br/>[FR] ANDROGÈNES À COUMARINE MODIFIÉE POUR LE TRAITEMENT DU CANCER DE LA PROSTATE
  申请人：HEALTH RESEARCH INC

  公开号：WO2020223174A1

  公开（公告）日：2020-11-05

  Provided are androstane and dihydrotestosterone compounds functionalized with carbocyclic groups or heterocyclic groups that may be saturated or unsaturated. The compounds may be used in methods of inhibiting cell growth of malignant cells and/or hyperplastic cells and/or treating individuals having diseases associated with malignant cell growth (e.g., cancer, such as, for example, prostate cancer) and/or hyperplastic cell growth and/or molecular imaging of malignant cells and/or hyperplastic cells and/or inducing degradation of a target protein. Also provided are compositions.

  提供的是功能化为碳环族或杂环族的雄烷和二氢睾酮化合物，这些化合物可能是饱和的或不饱和的。这些化合物可以用于抑制恶性细胞和/或增生细胞的细胞生长的方法，治疗患有与恶性细胞生长相关的疾病的个体（例如，癌症，例如前列腺癌）和/或增生细胞生长和/或恶性细胞和/或增生细胞的分子成像和/或诱导目标蛋白的降解。还提供了组合物。
• Sequence-determined DNA fragments and corresponding polypeptides encoded thereby
  申请人：Ceres Incorporated

  公开号：EP1033405A2

  公开（公告）日：2000-09-06

  The present invention provides DNA molecules that constitute fragments of the genome of a plant, and polypeptides encoded thereby. The DNA molecules are useful for specifying a gene product in cells, either as a promoter or as a protein coding sequence or as an UTR or as a 3' termination sequence, and are also useful in controlling the behavior of a gene in the chromosome, in controlling the expression of a gene or as tools for genetic mapping, recognizing or isolating identical or related DNA fragments, or identification of a particular individual organism, or for clustering of a group of organisms with a common trait. 0Arabidopsis DNA is used in the present experiment, but the procedure is a general one.

  本发明提供了构成植物基因组片段的 DNA 分子及其编码的多肽。这些 DNA 分子可作为启动子或蛋白质编码序列或 UTR 或 3'终止序列，用于指定细胞中的基因产物，也可用于控制染色体中基因的行为，控制基因的表达，或作为基因绘图、识别或分离相同或相关 DNA 片段、或识别特定生物个体、或对具有共同性状的生物群体进行聚类的工具。 本实验中使用的是拟南芥 DNA，但这是一个通用程序。
• DNA Sequences
  申请人：Ceres Incorporated

  公开号：EP1887081A2

  公开（公告）日：2008-02-13

  The present invention provides DNA molecules that constitute fragments of the genome of a plant, and polypeptides encoded thereby. The DNA molecules are useful for specifying a gene product in cells, either as a promoter or as a protein coding sequence or as an UTR or as a 3' termination sequence, and are also useful in controlling the behavior of a gene in the chromosome, in controlling the expression of a gene or as tools for genetic mapping, recognizing or isolating identical or related DNA fragments, or identification of a particular individual organism, or for clustering of a group of organisms with a common trait.

  本发明提供了构成植物基因组片段的 DNA 分子及其编码的多肽。这些 DNA 分子可作为启动子或蛋白质编码序列或 UTR 或 3'终止序列，用于指定细胞中的基因产物，也可用于控制染色体中基因的行为，控制基因的表达，或作为基因绘图、识别或分离相同或相关 DNA 片段、或识别特定生物个体或具有共同性状的生物群体的工具。
• Use of 3-alpha-androstanediol in the treatment of sexual dysfunction
  申请人：Emotional Brain B.V.

  公开号：EP1925307A1

  公开（公告）日：2008-05-28

  The invention relates to the field of male and/or female sexual dysfunction. The invention specifically relates to the use of 3-alpha-androstanediol, preferably in combination with a type 5 phosphodiesterase (PDE5) inhibitor and/or a 5-HT1A agonist. The invention also relates to the use of testosterone and a 5-HT1A agonist.

  本发明涉及男性和/或女性性功能障碍领域。本发明具体涉及 3-α-雄甾烷二醇的使用，最好与 5 型磷酸二酯酶（PDE5）抑制剂和/或 5-HT1A 激动剂结合使用。本发明还涉及睾酮和 5-HT1A 激动剂的使用。