5α-Pregnane-3α,11β-diol-20-one

5α-Pregnane-3α,11β-diol-20-one

Identifiers
CAS Number	565-89-9
3D model (JSmol)	Interactive image
PubChem CID	10125849
CompTox Dashboard (EPA)	DTXSID301275594
SMILES CC(=O)C1CCC2C1(CC(C3C2CCC4C3(CCC(C4)O)C)O)C
Properties
Chemical formula	C21H34O3
Molar mass	334.500 g·mol^−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

5α-Pregnane-3α,11β-diol-20-one, abbreviated as 3,11diOH-DHP4,[1] also known as 3α,11β-dihydroxy-5α-pregnan-20-one, is an endogenous steroid.[2][3][4]

The steroid 5α-pregnan-3α,11β-diol-20-one (3,11diOH-DHP4) plays a role in the 11-oxygenated steroid backdoor pathway to androgens as a metabolic intermediate. This pathway involves the metabolism of C₂₁ steroids (pregnanes) via enzymes such as steroid 11β-hydroxylase (CYP11B1), steroid 5α-reductase (SRD5A1), 17α-hydroxylase/17,20-lyase (CYP17A1), resulting in the production of androgen precursors.[5][1] Docking studies have shown that the C11-oxy group of 3,11diOH-DHP4 and alfaxalone does not significantly affect their binding to CYP17A1. Furthermore, it has been observed that the lyase activity of CYP17A1 is impaired by the C11-hydroxyl (-OH) and keto- (=O) moieties present in these steroids. The lyase activity of CYP17A1 converts intermediates like 3,11diOH-DHP4 to potent androgens such as 5α-pregnan-3α,11β,17α-triol-20-one (11OH-Pdiol). These findings indicate that CYP17A1 plays a role in the metabolism of this steroid through both hydroxylation and lyase reactions in the 11-oxygenated steroid backdoor pathway to androgens.[1][6] This pathway is important for regulating adrenal and gonadal steroid hormone biosynthesis and can contribute to elevated levels of androgens in certain conditions.[1][5][6]

References

1. van Rooyen D, Yadav R, Scott EE, Swart AC (May 2020). "CYP17A1 exhibits 17αhydroxylase/17,20-lyase activity towards 11β-hydroxyprogesterone and 11-ketoprogesterone metabolites in the C11-oxy backdoor pathway". J Steroid Biochem Mol Biol. 199: 105614. doi:10.1016/j.jsbmb.2020.105614. PMID 32007561. S2CID 210955834.
2. Ebner MJ, Corol DI, Havlíková H, Honour JW, Fry JP (January 2006). "Identification of neuroactive steroids and their precursors and metabolites in adult male rat brain" (PDF). Endocrinology. 147 (1): 179–90. doi:10.1210/en.2005-1065. PMID 16223859.
3. Yamada A, Yamada M, Fujita Y, Nishigami T, Nakasho K, Uematsu K (February 2001). "Self-augmentation effect of male-specific products on sexually differentiated progesterone metabolism in adult male rat liver microsomes". J Biol Chem. 276 (7): 4604–10. doi:10.1074/jbc.M003355200. PMID 10995741.
4. Ali HI, Yamada M, Fujita Y, Maeda M, Akaho E (2011). "Studies on 16α-Hydroxylation of Steroid Molecules and Regioselective Binding Mode in Homology-Modeled Cytochrome P450-2C11". Int J Med Chem. 2011: 918168. doi:10.1155/2011/918168. PMC 4970648. PMID 27516905.
5. Masiutin MM, Yadav MK (3 April 2023). "Alternative androgen pathways" (PDF). WikiJournal of Medicine. 10: 29. doi:10.15347/WJM/2023.003. S2CID 257943362. This article incorporates text from this source, which is available under the CC BY 4.0 license.
6. Slavíková B, Bujons J, Matyáš L, Vidal M, Babot Z, Krištofíková Z, Suñol C, Kasal A (March 2013). "Allopregnanolone and pregnanolone analogues modified in the C ring: synthesis and activity". J Med Chem. 56 (6): 2323–36. doi:10.1021/jm3016365. hdl:10261/89237. PMID 23421641.