5β-雙氫睾酮
5β-雙氫睾酮 | |
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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 | |
系統名 (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-羥基四環[8.7.0.02,7.011,15]-5-十七酮 | |
別名 | 5β-Androstan-17β-ol-3-one; Etiocholan-17β-ol-3-one; 5β-Dihydrotestosterone; 5β-DHT |
識別 | |
CAS號 | 571-22-2 |
PubChem | 11302 |
ChemSpider | 10827 |
SMILES |
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ChEBI | 2150 |
性質 | |
化學式 | C19H30O2 |
摩爾質量 | 290.44 g·mol−1 |
若非註明,所有數據均出自標準狀態(25 ℃,100 kPa)下。 |
5β-雙氫睾酮(英語:5β-Dihydrotestosterone,簡稱為5β-DHT,也稱為5β-雄甾烷-17β-醇-3-酮,5β-androstan-17β-ol-3-one,或本膽烷-17β-醇-3-酮,etiocholan-17β-ol-3-one)是一種本膽烷類(5β-雄烷)甾體物質,和睾酮的無雄激素活性的代謝產物,由肝臟和骨髓中的5β還原酶生成[1][2],同時也是生成3α-本膽烷二醇和3β-本膽烷二醇(分別由3α-和3β-羥基類固醇脫氫酶催化)的底物,之後再分別轉化為本膽烷醇酮和表本膽烷醇酮(由17β-羥基類固醇脫氫酶催化)[3][4]。和其表觀異構體5α-雙氫睾酮(5α-DHT或簡稱DHT)不同,5β-DHT只有非常弱的結合雄激素受體的能力[1]。作為主要的睾酮代謝產物,5β-DHT的A環和B環形之間的「順式」結構使兩個環在空間上形成了一個角度,故而缺乏了雄激素活性[5]。5β-DHT和5α-DHT的另一個不同點是,5β-DHT還缺乏神經甾體活性[6][7]但其代謝產物,本膽烷醇酮卻有神經甾體活性[8][9]。
另見
參考文獻
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