5-孕烯-3-beta, 16-alpha, 20-alpha-硫醇 | 3885-13-0

• 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: 5-孕烯-3-beta, 16-alpha, 20-alpha-硫醇
• 中文别名: 5-孕烯-3-beta,16-alpha,20-alpha-硫醇
• 英文名称: Δ⁵-pregnene-3β,16α,20α-triol
• 英文别名: Δ⁵-pregnene-3β,16α,20(S)-triol；Δ5-pregnene-3β,16α,20(S)-triol；3β,16α,20S-trihydroxypregn-5-ene；3,16,20-trihydroxypregn-5-ene；pregn-5-ene-3β,16α,20α_F-triol；Pregn-5-en-3β,16α,20α_F-triol；5-Pregnen-3beta,16alpha,20alpha-triol；(3S,8S,9S,10R,13S,14S,16R,17S)-17-[(1S)-1-hydroxyethyl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-3,16-diol
• CAS: 3885-13-0
• 化学式: C₂₁H₃₄O₃
• 分子量: 334.499
• InChiKey: BBYKCTWGEWBSOL-CNJDONEHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.9
• 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：

  5-孕烯-3-beta, 16-alpha, 20-alpha-硫醇 、 乙酸酐 在 吡啶 作用下， 生成 3β,16α,20α_F-triacetoxy-pregn-5-ene
  参考文献：
  名称：

  Hirschmann; Hirschmann, Journal of Biological Chemistry, 1945, vol. 157, p. 601,610

  摘要：

  DOI：
• 作为产物：
  描述：

  3β,16α-diacetoxy-20S-hydroxypregn-5-ene 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以47.6%的产率得到5-孕烯-3-beta, 16-alpha, 20-alpha-硫醇
  参考文献：
  名称：

  Woelfling, Janos; Magyar, Angela; Schneider, Gyula, Monatshefte fur Chemie, 2003, vol. 134, # 10, p. 1387 - 1393

  摘要：

  DOI：

文献信息

• Constituents of the chinese crude drug "Wujiapi". IX. Structure of glycoside H2, a potentiator of NGF-mediated nerve fiber outgrowth.
  作者：SEIICHI SAKUMA、SACHIKO KAWANISHI、JUNZO SHOJI

  DOI：10.1248/cpb.28.163

  日期：——

  Glycoside H2, C56H92O25, [α]D -25.9°(MeOH), which causes marked potentiation of the effect of NGF (nerve growth factor), was isolated from Bei-Wujiapi (the cortex of Periploca sepium BGE., Asclepiadaceae) and its chemical structure was established to be ⊿5-pregnene-3β, 16α, 20α-triol 3-O-[2-O-acetyl-β-D-digitalopyranosyl (1→4)-β-D-cymaro-pyranoside] 20-O-[β-D-glucopyranosyl (1→6)-β-D-glucopyranosyl (1→2)-β-D-digitalopyranoside] (1).

  从北五加皮（Periploca sepium BGE.的皮层）中分离出苷H2，C56H92O25，[α]D -25.9°(MeOH)，它能明显增强NGF（神经生长因子）的作用，并确定其化学结构为⊿5-孕烯-3β，16α，20α-triol 3-O-[2-O-乙酰-β-二ig]、5-孕烯-3β，16α，20α-三醇 3-O-[2-O-乙酰基-β-D-二吡喃糖基（1→4）-β-D-香豆吡喃糖苷] 20-O-[β-D-吡喃葡萄糖基（1→6）-β-D-吡喃葡萄糖基（1→2）-β-D-二吡喃糖苷] (1)。
• Pregnane glycosides from an antitumour fraction of Periploca sepium
  作者：Hideji itokawa、Junping Xu、Koichi Takeya

  DOI：10.1016/0031-9422(88)80297-8

  日期：——

  Abstract Three new pregnane glycosides (S-4a, S-5 and S-10) and two known pregnane glycosides (S-4b and S-6) were isolated from an antitumour fraction of the root barks of Periploca sepium. Their structures were determined by 1H and 13C NMR, FABMS and SIMS spectroscopy and some chemical transformations. One of the glycosides (S-4a) contained the new aglycone Δ5-pregnene-3β,16β,20(R)-triol.

  摘要 从 Periploca sepium 根皮的抗肿瘤成分中分离出三种新的孕烷苷（S-4a、S-5 和 S-10）和两种已知的孕烷苷（S-4b 和 S-6）。它们的结构由 1H 和 13C NMR、FABMS 和 SIMS 光谱以及一些化学转化确定。其中一种糖苷 (S-4a) 含有新的苷元 Δ5-pregnene-3β,16β,20(R)-triol。
• Cardenolide and Steroid Glycosides from Alafia sp., an Antimalarial Plant from Madagascar
  作者：M. F. Rakotondramanga、A. Raharisololalao、J. V. Rakotoarimanga、H. Ch. Krebs、L. Rasoanaivo、A. A. Razakarivony、R. Randrianasolo

  DOI：10.1007/s10600-016-1797-y

  日期：2016.9

  New cardenolide glycoside 1 and steroid glycoside 2, named respectively corotoxigenin-3-O-β- digitalopyranosyl-(1–4)-O-β-digitoxopyanoside and 5∆-pregnene-3β,16α,20(S)-diol 20-O-[β-Ddigitalopyranosyl (1→2)-β-D-glucopyranoside], have been isolated from the leaves of Alafia sp. (Apocynaceae). Compound 2 was isolated for the first time in its natural state, together with the known compounds digitoxin, corotoxigenin, and β-sitosteryl-3-O-β-D-glycopyranoside. The structures of compounds 1 and 2 were elucidated through spectroscopic techniques and chemical methods.

  新的心烯内酯糖苷1和类固醇糖苷2，分别命名为corotoxigenin-3-O-β-digitopyranosyl-(1–4)-O-β-digitoxopyanoside和5Δ-pregnene-3β,16α,20(S)-diol 20- O-[β-Ddigitalopyranosyl (1→2)-β-D-glucopyranoside]，已从 Alafia sp. 的叶子中分离出来。 （夹竹桃科）。化合物 2 首次以天然状态与已知化合物洋地黄毒苷、考罗毒配基和 β-谷甾醇-3-O-β-D-吡喃糖苷一起分离出来。通过光谱技术和化学方法阐明了化合物1和2的结构。
• A SYNTHESIS OF 16α-HYDROXY-20-KETOSTEROIDS AND THEIR CORRELATION WITH OTHER RING D SUBSTITUTED STEROIDS. THE CONFIGURATION OF THE SAPOGENIN SIDE CHAIN^{1, 2}
  作者：H. HIRSCHMANN、FRIEDA B. HIRSCHMANN、JOHN W. CORCORAN

  DOI：10.1021/jo01123a004

  日期：1955.5
• Camerino; Alberti, Gazzetta Chimica Italiana, 1955, vol. 85, p. 51,54
  作者：Camerino、Alberti

  DOI：——

  日期：——