1,3,5(10)-雌甾三烯-3,15-alpha,17-beta-三醇 | 570-30-9

• 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: 1,3,5(10)-雌甾三烯-3,15-alpha,17-beta-三醇
• 英文名称: 1,3,5-estratriene-3,15α,17β-triol
• 英文别名: 15α-hydroxyestradiol；3,15α,17β-Trihydroxy-oestratrien-<1,3,5(10)>；15α-Hydroxy-oestradiol；15alpha-Hydroxyestradiol；(8R,9S,13S,14S,15S,17S)-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-3,15,17-triol
• CAS: 570-30-9
• 化学式: C₁₈H₂₄O₃
• 分子量: 288.387
• InChiKey: QVQMPLATUBCZMQ-GVLSGGHMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  60.7
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,3,5(10)-雌甾三烯-3,15-alpha,17-beta-三醇 在 chromium(VI) oxide 、 硫酸 作用下， 生成 15-Oxo-14β-oestron
  参考文献：
  名称：

  Microbial Hydroxylation of Estrone and Estradiol in the 6β-, 7α-, and 15α-Positions

  摘要：

  DOI：

  10.1021/jo01029a014
• 作为产物：
  描述：

  estra-1,3,5(10),15-tetraene-3,17β-diol 在 咪唑 、 盐酸 作用下， 以 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 生成 1,3,5(10)-雌甾三烯-3,15-alpha,17-beta-三醇
  参考文献：
  名称：

  Syntheses of 15α-Hydroxyestrone and 15α-Hydroxyestradiol

  摘要：

  通过新的合成路线，我们从雌酮中制备出了标题化合物（1、2）。用二硼烷对 14、15 或 15、16-双键进行氢硼化合，然后用碱性过氧化氢对有机硼烷进行氧化，很容易在 15α 位上引入羟基。在制备 1 的过程中，为了保护 3、17β-羟基，方便地使用了二甲基叔丁基硅烷官能团。

  DOI：

  10.1248/cpb.23.3141

文献信息

• Microbial hydroxylation of 17β-estradiol by <i>Penicillium brevicompactum</i>
  作者：Lihong Shan、Yang Li、Yanjie Chen、Minghui Yin、Jiajia Huang、Zhenzhong Zhang、Xiufang Shi、Hongmin Liu

  DOI：10.1080/10242422.2016.1247816

  日期：2016.7.3

  Abstract Microbial hydroxylation of 17β-estradiol (1) with Penicillium brevicompactum, a fungal species not used in biotransformation so far, yielded four metabolites: 1, 3, 5-estratriene-3, 15α-diol-17-one (2); 1, 3, 5-estratriene-3, 6α, 17β-triol (3); 1, 3, 5-estratriene-3, 15α, 17β-triol (4); and 1, 3, 5-estratriene-3, 6α, 15α-triol-17-one (5). All the products were determined by 1H NMR, 13C NMR

  摘要 17β-雌二醇 (1) 与 Penicillium brevicompactum（一种迄今为止未用于生物转化的真菌物种）的微生物羟基化产生了四种代谢物：1, 3, 5-estratriene-3, 15α-diol-17-one (2)；1, 3, 5-estratriene-3, 6α, 17β-triol (3); 1, 3, 5-estratriene-3, 15α, 17β-triol (4); 和 1, 3, 5-estratriene-3, 6α, 15α-triol-17-one (5)。所有产物均通过1H NMR、13C NMR、二维NMR和HRMS技术测定。化合物3、4、5是首次通过微生物转化报道，5是目前已知的新化合物。还提出了 17β-雌二醇通过短青霉的可能代谢途径。
• Characterization of the Oxidative Metabolites of 17β-Estradiol and Estrone Formed by 15 Selectively Expressed Human Cytochrome P450 Isoforms
  作者：Anthony J. Lee、May Xiaoxin Cai、Paul E. Thomas、Allan H. Conney、Bao Ting Zhu

  DOI：10.1210/en.2003-0192

  日期：2003.8.1

  We systematically characterized the oxidative metabolites of 17β-estradiol and estrone formed by 15 human cytochrome P450 (CYP) isoforms. CYP1A1 had high activity for 17β-estradiol 2-hydroxylation, followed by 15α-, 6α-, 4-, and 7α-hydroxylation. However, when estrone was the substrate, CYP1A1 formed more 4-hydroxyestrone than 15α- or 6α-hydroxyestrone, with 2-hydroxyestrone as the major metabolite. CYP1A2 had the highest activity for the 2-hydroxylation of both 17β-estradiol and estrone, although it also had considerable activity for their 4-hydroxylation (9–13% of 2-hydroxylation). CYP1B1 mainly catalyzed the formation of catechol estrogens, with 4-hydroxyestrogens predominant. CYP2A6, 2B6, 2C8, 2C9, 2C19, and 2D6 each showed a varying degree of low catalytic activity for estrogen 2-hydroxylation, whereas CYP2C18 and CYP2E1 did not show any detectable estrogen-hydroxylating activity. CYP3A4 had strong activity for the formation of 2-hydroxyestradiol, followed by 4-hydroxyestradiol and an unknown polar metabolite, and small amounts of 16α- and 16β-hydroxyestrogens were also formed. The ratio of 4- to 2-hydroxylation of 17β-estradiol or estrone with CYP3A4 was 0.22 or 0.51, respectively. CYP3A5 had similar catalytic activity for the formation of 2- and 4- hydroxyestrogens. Notably, CYP3A5 had an unusually high ratio of 4- to 2-hydroxylation of 17β-estradiol or estrone (0.53 or 1.26, respectively). CYP3A4 and 3A5 also catalyzed the formation of nonpolar estrogen metabolite peaks (chromatographically less polar than estrone). CYP3A7 had a distinct catalytic activity for the 16α-hydroxylation of estrone, but not 17β-estradiol. CYP4A11 had little catalytic activity for the metabolism of 17β-estradiol and estrone. In conclusion, many human CYP isoforms are involved in the oxidative metabolism of 17β-estradiol and estrone, with a varying degree of catalytic activity and distinct regioselectivity.

  22-0.51)。
• Method and materials for detecting pathology from alterations in estrogen metabolism
  申请人：THE ROCKEFELLER UNIVERSITY

  公开号：EP0409176A2

  公开（公告）日：1991-01-23

  A method and associated materials for detecting pathology by determining alterations in estrogen metabolism in mammals are disclosed which comprise isolating at least two distinct metabolites of estrone from a biological sample taken from the mammal under examination, determining the quantity of each of the said metabolites in the sample, correlating the quantities of each of said metabolites with each other to arrive at a quotient of said metabolites, and comparing said quotient with an extrinsic quotient derived either previously from the mammal under test, as by the previous performance of the within test, or from the testing of other subjects of the same species, to determine any alterations in said estrogen metabolism from which such pathology, or pathologies, may be detected. The present method contemplates the investigation and use of products of enzymatic hydroxylation of estrone, enzymatic reduction of estrone, enzymatic oxidation of estrone, and enzymatic methylation of estrone. Methods of measurement of estrogen metabolites and related test kits are also disclosed.

  本发明公开了一种通过确定哺乳动物体内雌激素代谢的变化来检测病变的方法及相关材料，包括从被检哺乳动物的生物样本中分离出至少两种不同的雌酮代谢物，确定样本中每种代谢物的数量、将上述每种代谢物的数量相互关联，以得出上述代谢物的商数，并将上述商数与先前从受检哺乳动物（如先前进行的体内试验）或从同一物种的其他受试者的试验中得出的外在商数进行比较，以确定上述雌激素代谢中的任何改变，并从中检测出此类病理学或病理学。本方法考虑研究和使用雌酮的酶羟化产物、雌酮的酶还原产物、雌酮的酶氧化产物和雌酮的酶甲基化产物。此外，还公开了雌激素代谢物的测量方法和相关检测试剂盒。
• Steroids. CCLXI.¹ Microbiological Hydroxylation of Estrane Derivatives with Fusarium moniliforme
  作者：Pierre Crabbé、C. Casas-Campillo

  DOI：10.1021/jo01032a063

  日期：1964.9
• Preparation of specific antisera to 15α-hydroxyestrogens
  作者：Emako Suzuki、Madoka Nakagomi、Mitsunori Hashimoto、Manabu Agui、Sayaka Iida、Kazunori Konno、Yasuo Hara、Hiroyuki Kurihara、Yasuhiko Matsuki、Kiyoshi Imai、Hiroshi Ono

  DOI：10.1016/s0039-128x(99)00031-8

  日期：1999.8

  The synthesis of haptens of 15 alpha-hydroxyestrone, 15 alpha-hydroxyestradiol, and 15 alpha-hydroxyestriol (estetrol) was undertaken, to obtain specific antisera required for enzyme immunoassay. 3-(1-Carboxypropyl) ethers of these 15 alpha-hydroxyestrogens were prepared and conjugated with bovine serum albumin and horseradish peroxidase. The specificity of antisera elicited against bovine serum albumin conjugates was checked by the enzyme immunoassay by using horseradish peroxidase-labeled antigen, and proved to be satisfactory in terms of cross-reactivities to related compounds. (C) 1999 Elsevier Science Inc. All rights reserved.