别孕烷二醇

别孕烷二醇（英语：Allopregnanediol，又称5α-孕烷-3α,20α-二醇，5α-pregnane-3α,20α-diol）是一种内源的孕酮和别孕烷醇酮代谢产物，也是孕烷二醇（5β-孕烷-3α,20α-二醇）立体同分异构体^[2]。别孕烷二醇能作为别构调节GABA受体的部分激动剂，因此可能起到神经甾体的生物学作用^[3]，也能作为人孕烷X受体的激动剂，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  Y
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.