2-Alpha-羟基睾酮 | 4075-14-3

• 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
• 中文名称: 2-Alpha-羟基睾酮
• 英文名称: 2α-hydroxytestosterone
• 英文别名: 2α,17β-dihydroxyandrost-4-en-3-one；2α-Hydroxy-testosteron；2alpha-Hydroxytestosterone；(2R,8R,9S,10R,13S,14S,17S)-2,17-dihydroxy-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
• CAS: 4075-14-3
• 化学式: C₁₉H₂₈O₃
• 分子量: 304.43
• InChiKey: ZOIPFFUVGMVQGE-DTQPDNRZSA-N

物化性质

• 熔点：
  161-162 °C(Solv: acetone (67-64-1); hexane (110-54-3))
• 沸点：
  476.2±45.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  22
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

ADMET

代谢

2alpha-羟基睾酮是睾酮的一种已知人体代谢物。

2alpha-Hydroxytestosterone is a known human metabolite of testosterone.

来源:NORMAN Suspect List Exchange

安全信息

• 危险品标志：
  Xn
• 安全说明：
  S22,S36
• 危险类别码：
  R20/21/22,R40,R63

反应信息

• 作为反应物：
  描述：

  2-Alpha-羟基睾酮 在 二甲基亚砜 、 三氟乙酸 作用下， 生成 2,17β-dihydroxy-1,4-androstadien-3-one
  参考文献：
  名称：

  Morisawa,Y.; Tanabe,K., Chemical and pharmaceutical bulletin, 1969, vol. 17, # 6, p. 1206 - 1211

  摘要：

  DOI：
• 作为产物：
  描述：

  醋酸睾酮 在 lead(IV) acetate 、 potassium hydrogencarbonate 作用下， 生成 2-Alpha-羟基睾酮
  参考文献：
  名称：

  The Reaction of Lead Tetraacetate with Progesterone and Testosterone

  摘要：

  DOI：

  10.1021/ja01608a036

文献信息

• In‐depth gas chromatography/tandem mass spectrometry fragmentation analysis of formestane and evaluation of mass spectral discrimination of isomeric 3‐keto‐4‐ene hydroxy steroids
  作者：Annette Sophie Kollmeier、Xavier Torre、Christian Müller、Francesco Botrè、Maria Kristina Parr

  DOI：10.1002/rcm.8937

  日期：2020.12.30

  The aromatase inhibitor formestane (4‐hydroxyandrost‐4‐ene‐3,17‐dione) is included in the World Anti‐Doping Agency’s List of Prohibited Substances in Sport. However, it also occurs endogenously as do its 2‐, 6‐ and 11‐hydroxy isomers. The aim of this study is to distinguish the different isomers using GC/EI‐MS for enhanced confidence in detection and selectivity for determination.

  芳香酶抑制剂福尔马坦（4-羟基雄烷-4-烯-3,17-二酮）被列入世界反兴奋剂机构的《运动中禁用物质清单》。但是，它也像2-，6-和11-羟基异构体一样内源性地发生。这项研究的目的是使用GC / EI-MS区分不同的异构体，以增强检测的信心和测定的选择性。
• Constant Ion Loss Method for the Untargeted Detection of Bis-sulfate Metabolites
  作者：Malcolm D. McLeod、Christopher C. Waller、Argitxu Esquivel、Georgina Balcells、Rosa Ventura、Jordi Segura、Óscar J. Pozo

  DOI：10.1021/acs.analchem.6b03671

  日期：2017.2.7

  preferentially as the dianion ([M – 2H]2–) with a small contribution of the monoanion ([M – H]−). Product ion spectra generated from the [M – 2H]2– precursor ions were dominated by the loss of HSO4– to generate two product ions, that is, the ion at m/z 97 (HSO4–) and the ion corresponding to the remaining monosulfate fragment. Other product ions were found to be specific for some structures. As an example, the

  II期代谢物的非靶向检测是研究生物系统中药物代谢的关键问题。灵敏且选择性的质谱（MS）技术与超高效液相色谱（UHPLC）系统相结合是最有效的方法。在这项研究中，我们使用三重四极杆仪器评估了针对双硫酸盐代谢物的非目标检测的不同质谱方法。合成了23种甾体代谢物的双硫酸盐，并对其MS行为进行了全面研究。双硫酸盐优先离子化为二价阴离子（[M – 2H] 2–），而单阴离子（[M – H] -）的贡献很小。从[M – 2H] 2 –前体离子产生的产物离子光谱主要由HSO的损失决定4 –生成两个产物离子，即m / z 97处的离子（HSO 4 –）和对应于其余单硫酸盐片段的离子。发现其他产物离子对某些结构具有特异性。例如，发现[CH 3 + SO 3 ] -的损失对于与硫酸盐相邻的几种不饱和化合物很重要。根据双硫酸盐代谢物的常见行为，对两种选择方案进行了非靶向检测双硫酸盐代谢物的评估（i）使用m /
• Characterization of two steroid hydroxylases from different<i>Streptomyces</i>spp. and their ligand‐bound and ‐unbound crystal structures
  作者：Bikash Dangi、Chang Woo Lee、Ki‐Hwa Kim、Sun‐Ha Park、Eun‐Ji Yu、Chang‐Sook Jeong、Hyun Park、Jun Hyuck Lee、Tae‐Jin Oh

  DOI：10.1111/febs.14729

  日期：2019.5

  differences in the substrate-binding residues, suggesting a likely explanation for the different patterns of testosterone hydroxylation, despite the high sequence similarities between the enzymes (54% identity). These findings provide valuable insights that will enable protein engineering for the development of artificial steroid-related CYPs exhibiting different regiospecificity.

  细菌细胞色素P450（CYP）酶参与各种内源性底物的羟基化，同时使用血红素分子作为辅因子。CYPs作为有用的生物催化剂，能够通过以区域特异性方式添加羟基来改变化学结构，已引起了生物技术兴趣。在这里，我们从链霉菌属中鉴定，纯化和鉴定了两种CYP154C4蛋白。W2061（StCYP154C4-1）和链霉菌sp。ATCC 11861（StCYP154C4-2）。活性测定表明，StCYP154C4-1和StCYP154C4-2均可产生2'-羟基化的睾丸激素，这与先前描述的来自Nocardia farcinica的NfCYP154C5的活性在睾丸激素的16α-羟基化方面有所不同。为了更好地理解这两种CYP154C4蛋白的区域选择性的分子基础，测定了StCYP154C4-1的配体非结合形式和StCYP154C4-2的睾酮结合形式的晶体结构。与先前确定的NfCYP154C5结构的比较揭示了底物结合残基
• Purification and Characterization of Three Male-Specific and One Female-Specific Forms of Cytochrome P-450 from Rat Liver Microsomes1
  作者：Tatsumi MATSUMOTO、Yoshikazu EMI、Shun-ichirou KAWABATA、Tsuneo OMURA

  DOI：10.1093/oxfordjournals.jbchem.a121842

  日期：1986.10

  Three forms of cytochrome P-450, tentatively designated P-450(M-1), P-450(M-2), and P-450(M-3), and one form of cytochrome P-450, P-450(F-1), were purified from the liver microsomes of untreated male and female rats, respectively. Each purified form of the cytochrome showed a single protein band on SDS-polyacrylamide gel electrophoresis, and gave a minimum molecular weight of 51,000 for P-450M-1), 48,000 for P-450(M-2), 49,000 for P-450(M-3), and 50,000 for P450(F-1). The carbon monoxide-difference spectra of reduced P-450(M-1), P-450(M-2), P-450(M-3), and P-450(F-1) showed an absorption maximum at 451, 451, 448, and 449 nm, respectively. Judging from the absolute absorption spectra, the four forms of cytochrome P-450 were of low-spin type in the oxidized forms. The antibodies against P450(M-2) did not crossreact with the other forms in the Ouchterlony double diffusion test, whereas the immunodiffusion test showed immunocrossreactivity between P-450(M-1) and P-450(F-1), P-450(M-1) and P-450(M-3), and P-450(M-3) and P-450(F-1). The NH2-terminal amino acid sequences of the four forms confirmed that they were different molecular species, although significant homology was noticed among P-450(M-1), P-450(M-3), and P-450(F-1). The quantitation of P-450(M-1) and P-450(F-1) in liver microsomes by quantitative immunoprecipitation confirmed that these two forms of cytochrome P-450 were developmentally induced in male and female rats, respectively. P-450(M-2) was also developmentally induced in male rats. In a reconstituted system containing NADPH and NADPH-cytochrome P-450 reductase, P-450(M-1) oxidized benzphetamine at a high rate, whereas the other forms had low activity toward benzphetamine. None of the four forms showed high activity toward benzo(a)pyrene. P-450(M-1) catalyzed the hydroxylation of testosterone at the 16α and 2α positions, whereas P-450(M-2) catalyzed the 15α hydroxylation of the same substrate.

  从未经处理的雄性大鼠和雌性大鼠的肝脏微粒体中分别纯化出三种形式的细胞色素 P-450（暂定名为 P-450(M-1)、P-450(M-2)和 P-450(M-3)）和一种形式的细胞色素 P-450（P-450(F-1)）。每种纯化的细胞色素在 SDS 聚丙烯酰胺凝胶电泳上都显示出一条蛋白质条带，P-450M-1 的最小分子量为 51,000，P-450(M-2) 为 48,000，P-450(M-3) 为 49,000，P450(F-1) 为 50,000。）还原型 P-450(M-1)、P-450(M-2)、P-450(M-3)和 P-450(F-1)的一氧化碳差分光谱分别在 451、451、448 和 449 纳米波长处显示出吸收最大值。从绝对吸收光谱来看，这四种形式的细胞色素 P-450 在氧化状态下都属于低自旋型。在 Ouchterlony 双扩散试验中，P450(M-2)抗体与其他形式的细胞色素 P-450 没有交叉反应，而在免疫扩散试验中，P-450(M-1)与 P-450(F-1)、P-450(M-1)与 P-450(M-3)、P-450(M-3)与 P-450(F-1)之间存在免疫交叉反应。尽管 P-450(M-1)、P-450(M-3)和 P-450(F-1)之间存在明显的同源性，但四种形式的 NH2 端氨基酸序列证实它们是不同的分子物种。通过定量免疫沉淀法对肝脏微粒体中的 P-450（M-1）和 P-450（F-1）进行定量分析，证实这两种形式的细胞色素 P-450 在雄性大鼠和雌性大鼠体内分别是发育诱导的。雄性大鼠的 P-450（M-2）也是发育诱导的。在一个含有 NADPH 和 NADPH 细胞色素 P-450 还原酶的重组系统中，P-450(M-1) 以较高的速率氧化苯丙胺，而其他形式的细胞色素 P-450 对苯丙胺的活性较低。这四种形式对苯并(a)芘的活性都不高。P-450(M-1) 可催化睾酮在 16α 和 2α 位的羟基化，而 P-450(M-2) 可催化同一底物的 15α 羟基化。
• Cytochrome P450 hydroxylase, an important enzyme in brassinosteroid biosynthesis of plants
  申请人：Korea Kumho Petrochemical Co. Ltd.

  公开号：EP1209227A2

  公开（公告）日：2002-05-29

  The present invention provides a nucleic acid molecule encoding a dark-inducible cytochrome P450 hydroxylase that catalyzes the brassinosteroid biosynthesis through C-2 hydroxylations in plants. The invention also describes the methods and processes for generating expression cassettes and plasmids and for the use of these expression cassettes and plasmids to synthesize the cytochrome P450 hydroxylase or biologically active fragments of such an enzyme. The invention can be utilized to improve or decrease the stem growth of transgenic plants containing the nucleic acid molecule so that they exhibit improved growth rate and resistance to environmental stress and to identify other proteins involved in the brassinosteroid biosynthesis and in the plant growth regulation.

  本发明提供了一种编码暗诱导细胞色素P450羟化酶的核酸分子，该酶通过C-2羟化作用催化植物中铜绿素的生物合成。本发明还描述了生成表达盒和质粒以及使用这些表达盒和质粒合成细胞色素 P450 羟化酶或这种酶的生物活性片段的方法和过程。本发明可用于改善或降低含有核酸分子的转基因植物的茎部生长，使其表现出更好的生长速度和对环境胁迫的抵抗力，还可用于鉴定参与铜绿素生物合成和植物生长调节的其他蛋白质。