别孕烷二醇

化合物

别孕烷二醇(英語:Allopregnanediol,又称5α-孕烷-3α,20α-二醇,5α-pregnane-3α,20α-diol)是一种内源孕酮别孕烷醇酮代谢产物,也是孕烷二醇(5β-孕烷-3α,20α-二醇)立体同分异构[2]。别孕烷二醇能作为别构调节GABA受体部分激动剂,因此可能起到神经甾体的生物学作用[3],也能作为孕烷X受体激动剂,尽管EC50比其他内源性的孕烷衍生物(如孕烯醇酮、孕烷二醇、5α-双氢孕酮、别孕烷醇酮)低一个数量级以上[4]

别孕烷二醇
IUPAC名
(3R,5R,8R,9S,10S,13S,14S,17S)-17-[(1S)-1-Hydroxyethyl]-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol
系统名
(1S,2S,5R,7R,10R,11S,14S,15S)-14-[(1S)-1-hydroxyethyl]-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadecan-5-ol
(1S,2S,5R,7R,10R,11S,14S,15S)-2,5-二甲基-14-[(1S)-1-羟乙基]四环[8.7.0.02,7.011,15]-5-十七醇
识别
CAS号 566-58-5  checkY
PubChem 219833
SMILES
 
  • C[C@@H]([C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC[C@H]4[C@@]3(CC[C@H](C4)O)C)C)O
ChEBI 8387
性质
化学式 C21H36O2
摩尔质量 320.51 g·mol−1
熔点 241.5—244 °C(514.6—517.1 K)[1]
若非注明,所有数据均出自标准状态(25 ℃,100 kPa)下。

参考文献

  1. ^ Faith Ellen Francis, Ralph A. Kinsella. Enteric Excretion of Metabolites of Steroid Hormones in the Human Subject. V. Isolation of 5α-Pregnane-3α,20α-diol from Meconium. The Journal of Clinical Endocrinology & Metabolism. 1967-02, 27 (2): 211–213 [2019-10-22]. ISSN 0021-972X. doi:10.1210/jcem-27-2-211 (英语). 
  2. ^ Finn, Deborah A.; Purdy, Robert H. Neuroactive Steroids in Anxiety and Stress. 2007. doi:10.1002/9780470101001.hcn026. 
  3. ^ Belelli D, Gee KW. 5 alpha-pregnan-3 alpha,20 alpha-diol behaves like a partial agonist in the modulation of GABA-stimulated chloride ion uptake by synaptoneurosomes. Eur. J. Pharmacol. 1989, 167 (1): 173–6. PMID 2550257. doi:10.1016/0014-2999(89)90760-7. 
  4. ^ Ekins, Sean; Reschly, Erica J; Hagey, Lee R; Krasowski, Matthew D. Evolution of pharmacologic specificity in the pregnane X receptor. BMC Evolutionary Biology. 2008, 8 (1): 103. ISSN 1471-2148. PMC 2358886 . doi:10.1186/1471-2148-8-103.