11β-Hydroxytestosterone
Names
IUPAC name
11β,17β-Dihydroxyandrost-4-en-3-one
Systematic IUPAC name
(1S,3aS,3bS,9aR,9bS,11aS)-1,10-Dihydroxy-9a,11a-dimethyl-1,2,3,3a,3b,4,5,8,9,9a,9b,10,11,11a-tetradecahydro-7H-cyclopenta[a]phenanthren-7-one
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.162.057
EC Number
  • 634-040-0
KEGG
UNII
  • InChI=1S/C19H28O3/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/h9,13-17,21-22H,3-8,10H2,1-2H3/t13-,14-,15-,16-,17+,18-,19-/m0/s1
  • C1C2=CC(CC[C@@]2([C@]3([C@H](C[C@]4([C@]([C@@]3(C1)[H])(CC[C@@H]4O)[H])C)O)[H])C)=O
Properties
C19H28O3
Molar mass 304.430 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 °C [77 °F], 100 kPa).
Infobox references

11β-Hydroxytestosterone is an endogenous steroid, a metabolite of testosterone.[1][2][3][4] Although it may not have significant androgenic activity, it may still be an important precursor to androgenic molecules.[4]

See also

References

  1. ↑ Storbeck KH, Mostaghel EA (2019). "Canonical and Noncanonical Androgen Metabolism and Activity". Prostate Cancer. Advances in Experimental Medicine and Biology. Vol. 1210. Springer. pp. 239–277. doi:10.1007/978-3-030-32656-2_11. ISBN 978-3-030-32655-5. PMID 31900912. S2CID 209748543. CYP11B1 and 2 have also been shown to 11β-hydroxylate T, yielding 11β-hydroxytestosterone (11OHT), though the levels produced by the adrenal are low due to the limited availability of adrenal derived T
  2. ↑ Stárka L, Dušková M, Vítků J (September 2020). "11-Keto-testosterone and other androgens of adrenal origin". Physiological Research. 69 (Suppl 2): S187–S192. doi:10.33549/physiolres.934516. PMC 8603739. PMID 33094617.
  3. ↑ van Rooyen D, Gent R, Barnard L, Swart AC (2018). "The in vitro metabolism of 11β-hydroxyprogesterone and 11-ketoprogesterone to 11-ketodihydrotestosterone in the backdoor pathway". The Journal of Steroid Biochemistry and Molecular Biology. 178: 203–212. doi:10.1016/j.jsbmb.2017.12.014. PMID 29277707. S2CID 3700135.
  4. 1 2 Masiutin M, Yadav M (2023). "Alternative androgen pathways". WikiJournal of Medicine. 10: X. doi:10.15347/WJM/2023.003. S2CID 257943362.


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