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Identifiers | |
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3D model (
JSmol)
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PubChem
CID
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Properties | |
C21H34O3 | |
Molar mass | 334.5 |
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
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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. This pathway involves the metabolism of C21 steroids (pregnanes) via enzymes such as steroid 11β-hydroxylase (CYP11B1), steroid 5α-reductase (SRD5A1), cytochrome P450 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 and keto- 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-diol-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]
Category:Metabolic intermediates Category:Steroids