Chemistry: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[16]
Systematic IUPAC name
1-[(1R,3aS,3bR,5aS,7R,9aS,9bS,11aS)-1,7-Dihydroxy-9a,11a-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-1-yl]ethan-1-one
Other names
5α-pregnan-3α,17α-diol-20-one,[1][2][3] 5α-pregnane-3α,17α-diol-20-one,[4][5] 3α,5α-3,17-dihydroxypregnan-20-one,[6] 17-hydroxyallopregnanolone,[7][8][9][10][11][12] 17‐OH-allopregnanolone.[13][14][3][15]
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
EC Number
  • 229-994-6
Properties
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
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.

thumb|right|alt=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[17] in which 17α-hydroxyprogesterone (17‐OHP) is 5α-reduced and finally converted to 5α-dihydrotestosterone (DHT) without testosterone as a metabolic intermediate.[18][5]

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.[19][13][20]

Biosynthesis

5α-Pregnane-3α,17α-diol-20-one is produced from 5α-pregnan-17α-ol-3,20-dione[21] in a reaction catalyzed by a reductive 3α-hydroxysteroid dehydrogenase (3α-HSD),[22] i.e. by the two aldo-keto reductase isozymes: AKR1C2 and AKR1C4,[23] and by 17β-hydroxysteroid dehydrogenase 6 (HSD17B6) that also has the 3α-HSD activity.[23]

See also

References

  1. ↑ "Adrenal C11-oxy C21 steroids contribute to the C11-oxy C19 steroid pool via the backdoor pathway in the biosynthesis and metabolism of 21-deoxycortisol and 21-deoxycortisone". The Journal of Steroid Biochemistry and Molecular Biology 174: 86–95. November 2017. doi:10.1016/j.jsbmb.2017.07.034. PMID 28774496. 
  2. ↑ "Regulation of Steroidogenesis". Cellular Endocrinology in Health and Disease. Academic Press. 2014. pp. 207–227. doi:10.1016/B978-0-12-408134-5.00013-5. ISBN 978-0-12-408134-5. https://www.sciencedirect.com/science/article/pii/B9780124081345000135. "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. ↑ 3.0 3.1 "5alpha-reduced C21 steroids are substrates for human cytochrome P450c17". Archives of Biochemistry and Biophysics 418 (2): 151–160. October 2003. doi:10.1016/j.abb.2003.07.003. PMID 14522586. 
  4. ↑ "5alpha-androstane-3alpha,17beta-diol is formed in tammar wallaby pouch young testes by a pathway involving 5alpha-pregnane-3alpha,17alpha-diol-20-one as a key intermediate". Endocrinology 144 (2): 575–580. February 2003. doi:10.1210/en.2002-220721. PMID 12538619. 
  5. ↑ 5.0 5.1 "Increased activation of the alternative "backdoor" pathway in patients with 21-hydroxylase deficiency: evidence from urinary steroid hormone analysis". The Journal of Clinical Endocrinology and Metabolism 97 (3): E367–E375. March 2012. doi:10.1210/jc.2011-1997. PMID 22170725. 
  6. ↑ "ChemSpider Chemical Structure: 99828". http://www.chemspider.com/Chemical-Structure.99828.html. 
  7. ↑ Cytochrome P450: Structure, Mechanism, and Biochemistry. Springer. 13 March 2015. ISBN 9783319121086. https://books.google.com/books?id=abZnBwAAQBAJ&q=%2217-hydroxyallopregnanolone%22&pg=PA851. "17-OH-Allo 5α-pregnane-3α,17α-diol-20-one (17-hydroxyallopregnanolone)" 
  8. ↑ "The alternative pathway of fetal androgen synthesis (Homo sapiens)". 23 June 2021. https://www.wikipathways.org/index.php/Pathway:WP4524. "17-Hydroxyallopregnanolone, Metabolite, CHEBI:11909 (ChEBI)" 
  9. ↑ "Prenatal diagnosis of congenital adrenal hyperplasia caused by P450 oxidoreductase deficiency". The Journal of Clinical Endocrinology and Metabolism 98 (3): E528–E536. March 2013. doi:10.1210/jc.2012-3449. PMID 23365120. "17-hydroxyallopregnanolone (5-pregnane-3,17-diol-20-one)". 
  10. ↑ "Steroidogenic potential of lyophilized mitochondria from bovine adrenocortical tissue". Proceedings of the National Academy of Sciences of the United States of America 89 (9): 4173–4177. May 1992. doi:10.1073/pnas.89.9.4173. PMID 1570344. Bibcode: 1992PNAS...89.4173P. 
  11. ↑ "Activation of Adrenal Steroidogenesis and an Improvement of Mood Balance in Postmenopausal Females after Spa Treatment Based on Physical Activity". International Journal of Molecular Sciences 20 (15): 3687. July 2019. doi:10.3390/ijms20153687. PMID 31357645. 
  12. ↑ "Evidence for the existence and significance of an alternative pathway towards androgen synthesis during early human life". Endocrine Abstracts 25. April 2011. https://www.endocrine-abstracts.org/ea/0025/ea0025oc1.6. 
  13. ↑ 13.0 13.1 "Backdoor pathway for dihydrotestosterone biosynthesis: implications for normal and abnormal human sex development". Developmental Dynamics 242 (4): 320–329. April 2013. doi:10.1002/dvdy.23892. PMID 23073980. 
  14. ↑ "Beyond T and DHT - novel steroid derivatives capable of wild type androgen receptor activation". International Journal of Biological Sciences 10 (6): 602–613. 2014. doi:10.7150/ijbs.8844. PMID 24948873. 
  15. ↑ "Steroidogenic pathways involved in androgen biosynthesis in eumenorrheic women and patients with polycystic ovary syndrome". The Journal of Steroid Biochemistry and Molecular Biology 158: 31–37. April 2016. doi:10.1016/j.jsbmb.2016.02.010. PMID 26877255. 
  16. ↑ "3α,17-dihydroxy-5α-pregnan-20-one substance infocard". https://echa.europa.eu/sl/substance-information/-/substanceinfo/100.027.267. 
  17. ↑ "Alternative androgen pathways". WikiJournal of Medicine 10: X. 2023. doi:10.15347/WJM/2023.003. 
  18. ↑ "The backdoor pathway to dihydrotestosterone". Trends in Endocrinology and Metabolism 15 (9): 432–438. November 2004. doi:10.1016/j.tem.2004.09.004. PMID 15519890. 
  19. ↑ "Alternative (backdoor) androgen production and masculinization in the human fetus". PLOS Biology 17 (2): e3000002. February 2019. doi:10.1371/journal.pbio.3000002. PMID 30763313. 
  20. ↑ "The "backdoor pathway" of androgen synthesis in human male sexual development". PLOS Biology 17 (4): e3000198. April 2019. doi:10.1371/journal.pbio.3000198. PMID 30943210. 
  21. ↑ "46,XX DSD due to Androgen Excess in Monogenic Disorders of Steroidogenesis: Genetic, Biochemical, and Clinical Features". International Journal of Molecular Sciences 20 (18): 4605. September 2019. doi:10.3390/ijms20184605. PMID 31533357. 
  22. ↑ ""Getting from here to there"--mechanisms and limitations to the activation of the androgen receptor in castration-resistant prostate cancer". Journal of Investigative Medicine 58 (8): 938–944. December 2010. doi:10.2310/JIM.0b013e3181ff6bb8. PMID 21030877. "The product of 17-hydroxyprogesterone reduction, 5α-pregnan-17α-ol-3,20-dione, was metabolized by a reductive 3α-HSD to a new key intermediate, 5α-pregnane-3α,17α-diol-20-one (Pdiol)". 
  23. ↑ 23.0 23.1 "The syndrome of 17,20 lyase deficiency". The Journal of Clinical Endocrinology and Metabolism 97 (1): 59–67. January 2012. doi:10.1210/jc.2011-2161. PMID 22072737. 




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