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5α-Pregnane-3α,17α-diol-20-one

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5α-Pregnane-3α,17α-diol-20-one
Names
IUPAC name 3α,17-Dihydroxy-5α-pregnan-20-one
Systematic IUPAC name 1-phenanthren-1-yl]ethan-1-one
Other names 5α-pregnan-3α,17α-diol-20-one, 5α-pregnane-3α,17α-diol-20-one, 3α,5α-3,17-dihydroxypregnan-20-one, 17-hydroxyallopregnanolone, 17-OH-allopregnanolone.
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
EC Number
  • 229-994-6
PubChem CID
CompTox Dashboard (EPA)
InChI
  • Key: LKQDFQLSEHWIRK-JRRMKBMNSA-N
  • InChI=1S/C21H34O3/c1-13(22)21(24)11-8-18-16-5-4-14-12-15(23)6-9-19(14,2)17(16)7-10-20(18,21)3/h14-18,23-24H,4-12H2,1-3H3/t14-,15+,16+,17-,18-,19-,20-,21-/m0/s1
SMILES
  • CC(=O)1(CC21(CC32CC43(CC(C4)O)C)C)O
Properties
Chemical formula C21H34O3
Molar mass 334.500 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound
Comparison of chemical structures for allopregnane, allopregnanolone and 5α-Pregnane-3α,17α-diol-20-one (17α-allopregnanolone). Please note that the difference between the allopregnanolone and 5α-Pregnane-3α,17α-diol-20-one is a hydroxyl function group (−OH) at C17 position.
Complex chemical diagram
Structure of cholestane, a steroid with 27 carbon atoms. Its core ring system (ABCD), composed of 17 carbon atoms, is shown with IUPAC-approved ring lettering and atom numbering.

5α-Pregnane-3α,17α-diol-20-one, also known as 17α-hydroxyallopregnanolone (17-OH-allo) is an endogenous steroid.

Function

5α-Pregnane-3α,17α-diol-20-one is a metabolite, an intermediate product within the androgen backdoor pathway in which 17α-hydroxyprogesterone (17-OHP) is 5α-reduced and finally converted to 5α-dihydrotestosterone (DHT) without testosterone as a metabolic intermediate.

The pathway can be outlined as 17-OHP → 5α-pregnan-17α-ol-3,20-dione → 5α-pregnane-3α,17α-diol-20-one → androsterone → 5α-androstane-3α,17β-diol → DHT.

Biosynthesis

5α-Pregnane-3α,17α-diol-20-one is produced from 5α-pregnan-17α-ol-3,20-dione in a reaction catalyzed by a reductive 3α-hydroxysteroid dehydrogenase (3α-HSD), i.e. by the two aldo-keto reductase isozymes: AKR1C2 and AKR1C4, and by 17β-hydroxysteroid dehydrogenase 6 (HSD17B6) that also has the 3α-HSD activity.

See also

References

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  2. Bremer AA, Miller WL (2014). "Regulation of Steroidogenesis". Cellular Endocrinology in Health and Disease. Academic Press. pp. 207–227. doi:10.1016/B978-0-12-408134-5.00013-5. ISBN 978-0-12-408134-5. Archived from the original on 24 October 2020. Retrieved 21 October 2020. Most steroids are identified by their common names; 17-hydroxy-dihydroprogesterone (17OH-DHP) is 5α-pregnane-17α-ol-3,20-dione; 17-hydroxy-allopregnanolone (17OH-allo) is 5α-pregnan-3α,17α-diol-20-one; 5α-dihydroprogesterone (5α-DHP) is 5α-pregnane-3,20-dione, and allopregnanolone is 3α-hydroxy-dihydroprogesterone (3α-OH-DHP) or 5α-pregnane-3α-ol-20-one.
  3. ^ Gupta MK, Guryev OL, Auchus RJ (October 2003). "5alpha-reduced C21 steroids are substrates for human cytochrome P450c17". Archives of Biochemistry and Biophysics. 418 (2): 151–160. doi:10.1016/j.abb.2003.07.003. PMID 14522586.
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  12. Reisch N, Dhir V, Berry A, Taylor A, Krone N, Nogueira E, Shackleton C, Hanley N, Arlt W (April 2011). "Evidence for the existence and significance of an alternative pathway towards androgen synthesis during early human life". Endocrine Abstracts. 25. Archived from the original on 11 August 2020. Retrieved 4 November 2020.
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  23. ^ Miller WL (January 2012). "The syndrome of 17,20 lyase deficiency". The Journal of Clinical Endocrinology and Metabolism. 97 (1): 59–67. doi:10.1210/jc.2011-2161. PMC 3251937. PMID 22072737.
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