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5β-双氢睾酮

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5β-双氢睾酮
IUPAC名
(5R,8R,9S,10S,13S,14S,17S)-17-Hydroxy-10,13-dimethyl-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-one
系统名
(1S,2R,7R,10R,11S,14S,15S)-14-hydroxy-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadecan-5-one

(1S,2R,7R,10R,11S,14S,15S)-2,15-二甲基-14-羟基四环[8.7.0.02,7.011,15]-5-十七酮

别名 5β-Androstan-17β-ol-3-one; Etiocholan-17β-ol-3-one; 5β-Dihydrotestosterone; 5β-DHT
识别
CAS号 571-22-2
PubChem 11302
ChemSpider 10827
SMILES
 
  • C[C@]12CCC(=O)C[C@H]1CC[C@@H]3[C@@H]2CC[C@]4([C@H]3CC[C@@H]4O)C
ChEBI 2150
性质
化学式 C19H30O2
摩尔质量 290.44 g·mol−1
若非注明,所有数据均出自标准状态(25 ℃,100 kPa)下。

5β-双氢睾酮(英语:5β-Dihydrotestosterone,简称为5β-DHT,也称为5β-雄甾烷-17β-醇-3-酮,5β-androstan-17β-ol-3-one,或本胆烷-17β-醇-3-酮,etiocholan-17β-ol-3-one)是一种本胆烷类(5β-雄烷甾体物质,和睾酮的无雄激素活性的代谢产物,由肝脏骨髓中的5β还原酶生成[1][2],同时也是生成3α-本胆烷二醇3β-本胆烷二醇(分别由3α-3β-羟基类固醇脱氢酶催化)的底物,之后再分别转化为本胆烷醇酮表本胆烷醇酮(由17β-羟基类固醇脱氢酶催化)[3][4]。和其表观异构体5α-双氢睾酮(5α-DHT或简称DHT)不同,5β-DHT只有非常弱的结合雄激素受体的能力[1]。作为主要的睾酮代谢产物,5β-DHT的A环和B环形之间的“顺式”结构使两个环在空间上形成了一个角度,故而缺乏了雄激素活性[5]。5β-DHT和5α-DHT的另一个不同点是,5β-DHT还缺乏神经甾体活性[6][7]但其代谢产物,本胆烷醇酮却有神经甾体活性[8][9]

另见

参考文献

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  9. ^ Kaminski RM, Marini H, Kim WJ, Rogawski MA. Anticonvulsant activity of androsterone and etiocholanolone. Epilepsia. June 2005, 46 (6): 819–27. PMC 1181535可免费查阅. PMID 15946323. doi:10.1111/j.1528-1167.2005.00705.x.