11β-Hydroxydihydrotestosterone

Chemical compound From Wikipedia, the free encyclopedia

11β-Hydroxydihydrotestosterone (11OHDHT) is an endogenous steroid.[1] Although it may not have significant androgenic activity, it may still be an important precursor to androgenic molecules.[2]

Quick facts Names, Identifiers ...
11β-Hydroxydihydrotestosterone
Names
IUPAC name
11β,17β-dihydroxy-5α-androstan-3-one
Systematic IUPAC name
(5S,8S,9S,10S,11S,13S,14S,17S)-11,17-dihydroxy-10,13-dimethyl-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-one
Other names
5α-androstan-11β,17β-diol-3-one
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C19H30O3/c1-18-8-7-12(20)9-11(18)3-4-13-14-5-6-16(22)19(14,2)10-15(21)17(13)18/h11,13-17,21-22H,3-10H2,1-2H3/t11-,13-,14-,15-,16-,17+,18-,19-/m0/s1
  • C1CC(=O)C[C@]2([H])CC[C@@]3([H])[C@]4([H])CC[C@H](O)[C@@]4(C)C[C@H](O)[C@]3([H])[C@@]12C
Properties
C19H30O3
Molar mass 306.446 g·mol−1
Hazards
GHS labelling:
GHS08: Health hazard
Danger
H351, H360
P201, P202, P281, P308+P313, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 Â°C [77 Â°F], 100 kPa).
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Biological role

11OHDHT, along with other carbon-11-oxygenated (C11-oxy) steroids, 11-ketodihydrotestosterone (11KDHT) and 11-ketotestosterone (11KT), are androgen receptor (AR) agonists. The interconversion of C11-oxy C19 steroids, which includes 11OHDHT, was found to be more efficient than that of C11-oxy C21 steroids. 11OHDHT was also found to exhibit antagonism towards the progesterone receptor B (PRB), although it is not a pregnane (C21) steroid, highlighting the intricate interplay between receptors and active as well as "inactive" C11-oxy steroids.[2]

See also

External links

References

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