Androst-5-ene-3beta,17beta-diol
IUPAC 名称
(1S,2R,5S,10R,11S,14S,15S)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-ene-5,14-diol
描述
Androstenediol is a term used to refer to two different steroids with molecular weights of 290.44: '4-androstenediol' (4-androstene-3beta,17beta-diol) and '5-androstenediol' (5-androstene-3beta,17beta-diol). 4-Androstenediol is closer to testosterone structurally, and has androgenic effects. 5-Androstenediol is a direct metabolite of the most abundant steroid produced by the human adrenal cortex, dehydroepiandrosterone (DHEA). 5-Androstenediol is less androgenic than 4-androstenediol, and stimulates the immune system. When administered to rats in vivo, 5-androstenediol has approximately 1/70 the androgenicity of DHEA, 1/185 the androgenicity of androstenedione, and 1/475 the androgenicity of testosterone (Coffey, 1988). Because it induces production of white blood cells and platelets, 5-androstenediol is being developed as a radiation countermeasure as Neumune(HE2100).
An intermediate in testosterone biosynthesis, found in the testis or the adrenal. Androstenediol, derived from dehydroepiandrosterone by the reduction of the 17-keto group (17-fydroxysteroid dehydrogenaseS), is converted to testosterone by the oxidation of the 3-beta hydroxyl group to a 3-keto group (3-fydroxysteroid dehydrogenase). [HMDB]
异构
[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@@H](O)CC[C@]12C
InChI标识符
InChI=1S/C19H30O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h3,13-17,20-21H,4-11H2,1-2H3/t13-,14-,15-,16-,17-,18-,19-/m0/s1
键
QADHLRWLCPCEKT-LOVVWNRFSA-N