View source for Chemistry:5α-Pregnane-3α,17α-diol-20-one

 {{cs1 config|name-list-style=vanc}}{{Chembox
<!-- Images -->
| ImageFile = {{wikidata|property|raw|P117}}
| ImageSize =
| ImageAlt =
<!-- Names -->
| IUPACName = 3α,17-Dihydroxy-5α-pregnan-20-one<ref name="infocard">{{cite web |url=https://echa.europa.eu/sl/substance-information/-/substanceinfo/100.027.267 |title=3α,17-dihydroxy-5α-pregnan-20-one substance infocard}}</ref>
| SystematicName = 1-[(1''R'',3a''S'',3b''R'',5a''S'',7''R'',9a''S'',9b''S'',11a''S'')-1,7-Dihydroxy-9a,11a-dimethylhexadecahydro-1''H''-cyclopenta[''a'']phenanthren-1-yl]ethan-1-one
| OtherNames = 5α-pregnan-3α,17α-diol-20-one,<ref name="pmid28774496">{{cite journal | vauthors = Barnard L, Gent R, van Rooyen D, Swart AC | title = Adrenal C11-oxy C<sub>21</sub> steroids contribute to the C11-oxy C<sub>19</sub> steroid pool via the backdoor pathway in the biosynthesis and metabolism of 21-deoxycortisol and 21-deoxycortisone | journal = The Journal of Steroid Biochemistry and Molecular Biology | volume = 174 | pages = 86–95 | date = November 2017 | pmid = 28774496 | doi = 10.1016/j.jsbmb.2017.07.034 | s2cid = 24071400 }}</ref><ref name="Cellular-2014">{{cite book |title=Cellular Endocrinology in Health and Disease|chapter=Regulation of Steroidogenesis |year=2014 |pages=207–227 |quote=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.|chapter-url=https://www.sciencedirect.com/science/article/pii/B9780124081345000135 |doi=10.1016/B978-0-12-408134-5.00013-5 |isbn=978-0-12-408134-5 | vauthors = Bremer AA, Miller WL |publisher=Academic Press }}</ref><ref name="pmid14522586">{{cite journal | vauthors = Gupta MK, Guryev OL, Auchus RJ | title = 5alpha-reduced C21 steroids are substrates for human cytochrome P450c17 | journal = Archives of Biochemistry and Biophysics | volume = 418 | issue = 2 | pages = 151–160 | date = October 2003 | pmid = 14522586 | doi = 10.1016/j.abb.2003.07.003 }}</ref> 5α-pregnane-3α,17α-diol-20-one,<ref name="pmid12538619">{{cite journal | vauthors = Wilson JD, Auchus RJ, Leihy MW, Guryev OL, Estabrook RW, Osborn SM, Shaw G, Renfree MB | display-authors = 6 | title = 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 | journal = Endocrinology | volume = 144 | issue = 2 | pages = 575–580 | date = February 2003 | pmid = 12538619 | doi = 10.1210/en.2002-220721 | doi-access = free }}</ref><ref name="pmid22170725"/> 3α,5α-3,17-dihydroxypregnan-20-one,<ref name="ChemSipider99828">{{cite web|url=http://www.chemspider.com/Chemical-Structure.99828.html | title=ChemSpider Chemical Structure: 99828}}</ref> 17-hydroxyallopregnanolone,<ref name="Springer-2015">{{cite book |url=https://books.google.com/books?id=abZnBwAAQBAJ&q=%2217-hydroxyallopregnanolone%22&pg=PA851 |quote=17-OH-Allo 5α-pregnane-3α,17α-diol-20-one (17-hydroxyallopregnanolone)|title=Cytochrome P450: Structure, Mechanism, and Biochemistry|date=13 March 2015|publisher=Springer |isbn=9783319121086}}</ref><ref name="Sanders-2021">{{cite web |url=https://www.wikipathways.org/index.php/Pathway:WP4524 |title=The alternative pathway of fetal androgen synthesis (Homo sapiens)|date=23 June 2021 |quote=17-Hydroxyallopregnanolone, Metabolite, CHEBI:11909 (ChEBI)| vauthors = Sanders E, Slenter D, Willighagen E, Hemel I, Bot WM, Ehrhart F, Weitz E, Hu F | display-authors = 6 }}</ref><ref name="pmid23365120">{{cite journal | vauthors = Reisch N, Idkowiak J, Hughes BA, Ivison HE, Abdul-Rahman OA, Hendon LG, Olney AH, Nielsen S, Harrison R, Blair EM, Dhir V, Krone N, Shackleton CH, Arlt W | display-authors = 6 | title = Prenatal diagnosis of congenital adrenal hyperplasia caused by P450 oxidoreductase deficiency | journal = The Journal of Clinical Endocrinology and Metabolism | volume = 98 | issue = 3 | pages = E528–E536 | date = March 2013 | pmid = 23365120 | pmc = 3708032 | doi = 10.1210/jc.2012-3449 | quote = 17-hydroxyallopregnanolone (5-pregnane-3,17-diol-20-one) }}</ref><ref name="pmid1570344">{{cite journal | vauthors = Prasad VV, Mathur C, Welch M, Lieberman S | title = Steroidogenic potential of lyophilized mitochondria from bovine adrenocortical tissue | journal = Proceedings of the National Academy of Sciences of the United States of America | volume = 89 | issue = 9 | pages = 4173–4177 | date = May 1992 | pmid = 1570344 | pmc = 525655 | doi = 10.1073/pnas.89.9.4173 | doi-access = free | bibcode = 1992PNAS...89.4173P }}</ref><ref name="pmid31357645">{{cite journal | vauthors = Honců P, Hill M, Bičíková M, Jandová D, Velíková M, Kajzar J, Kolátorová L, Bešťák J, Máčová L, Kancheva R, Krejčí M, Novotný J, Stárka Ľ | display-authors = 6 | title = Activation of Adrenal Steroidogenesis and an Improvement of Mood Balance in Postmenopausal Females after Spa Treatment Based on Physical Activity | journal = International Journal of Molecular Sciences | volume = 20 | issue = 15 | page = 3687 | date = July 2019 | pmid = 31357645 | pmc = 6695846 | doi = 10.3390/ijms20153687 | doi-access = free }}</ref><ref name="Reisch-2011">{{cite journal |url=https://www.endocrine-abstracts.org/ea/0025/ea0025oc1.6 |title=Evidence for the existence and significance of an alternative pathway towards androgen synthesis during early human life|journal=Endocrine Abstracts|date=April 2011|volume=25 | vauthors =  Reisch N, Dhir V, Berry A, Taylor A, Krone N, Nogueira E, Shackleton C, Hanley N, Arlt W }}</ref> 17‐OH-allopregnanolone.<ref name="pmid23073980"/><ref name="pmid24948873">{{cite journal | vauthors = Mostaghel EA | title = Beyond T and DHT - novel steroid derivatives capable of wild type androgen receptor activation | journal = International Journal of Biological Sciences | volume = 10 | issue = 6 | pages = 602–613 | year = 2014 | pmid = 24948873 | pmc = 4062953 | doi = 10.7150/ijbs.8844 }}</ref><ref name="pmid14522586"/><ref name="pmid26877255">{{cite journal | vauthors = Saito K, Matsuzaki T, Iwasa T, Miyado M, Saito H, Hasegawa T, Homma K, Inoue E, Miyashiro Y, Kubota T, Irahara M, Ogata T, Fukami M | display-authors = 6 | title = Steroidogenic pathways involved in androgen biosynthesis in eumenorrheic women and patients with polycystic ovary syndrome | journal = The Journal of Steroid Biochemistry and Molecular Biology | volume = 158 | pages = 31–37 | date = April 2016 | pmid = 26877255 | doi = 10.1016/j.jsbmb.2016.02.010 | s2cid = 22243788 }}</ref>

<!-- Sections -->
| Section1 = {{Chembox Identifiers
| CASNo = 6890-65-9
| EC_number = 229-994-6
| PubChem = 111243
| ChEBI = 194477
| ChemSpiderID = 99828
| 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
| StdInChIKey = LKQDFQLSEHWIRK-JRRMKBMNSA-N
<!-- Isomeric SMILE from the PubChem database -->
| SMILES = CC(=O)[C@]1(CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC[C@@H]4[C@@]3(CC[C@H](C4)O)C)C)O
  }}
| Section2 = {{Chembox Properties
| C=21 | H=34 | O=3
| MolarMass =
| Appearance =
| Density =
| MeltingPt =
| BoilingPt =
| Solubility =
  }}
| Section3 = {{Chembox Hazards
| MainHazards =
| FlashPt =
| AutoignitionPt =
  }}
}}[[Image:17-alpha-hydroxyallopregnanolone-comparison-3-pregnanes.svg|right|thumb|Comparison of chemical structures for [[Chemistry:Allopregnane|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 [[Biology:Steroid|steroid]].

== Function ==
5α-Pregnane-3α,17α-diol-20-one is a [[Biology:Metabolite|metabolite]], an intermediate product within the [[Biology:Androgen backdoor pathway|androgen backdoor pathway]]<ref name=wj>{{cite journal|doi=10.15347/WJM/2023.003  |doi-access=free|title=Alternative androgen pathways |year=2023 | vauthors = Masiutin M, Yadav M |journal=WikiJournal of Medicine |volume=10 |pages=X |s2cid=257943362}}</ref> in which 17α-hydroxyprogesterone (17‐OHP) is [[Chemistry:5α-reductase|5α-reduced]] and finally converted to 5α-dihydrotestosterone (DHT) without [[Chemistry:Testosterone|testosterone]] as a [[Biology:Metabolic intermediate|metabolic intermediate]].<ref name="pmid15519890">{{cite journal | vauthors = Auchus RJ | title = The backdoor pathway to dihydrotestosterone | journal = Trends in Endocrinology and Metabolism | volume = 15 | issue = 9 | pages = 432–438 | date = November 2004 | pmid = 15519890 | doi = 10.1016/j.tem.2004.09.004 | s2cid = 10631647 }}</ref><ref name="pmid22170725">{{cite journal | vauthors = Kamrath C, Hochberg Z, Hartmann MF, Remer T, Wudy SA | title = Increased activation of the alternative "backdoor" pathway in patients with 21-hydroxylase deficiency: evidence from urinary steroid hormone analysis | journal = The Journal of Clinical Endocrinology and Metabolism | volume = 97 | issue = 3 | pages = E367–E375 | date = March 2012 | pmid = 22170725 | doi = 10.1210/jc.2011-1997 | doi-access = free }}</ref>

The pathway can be outlined as 17-OHP → 5α-pregnan-17α-ol-3,20-dione → 5α-pregnane-3α,17α-diol-20-one → [[Biology:Androsterone|androsterone]] → 5α-androstane-3α,17β-diol → DHT.<ref name="pmid30763313">{{cite journal | vauthors = O'Shaughnessy PJ, Antignac JP, Le Bizec B, Morvan ML, Svechnikov K, Söder O, Savchuk I, Monteiro A, Soffientini U, Johnston ZC, Bellingham M, Hough D, Walker N, Filis P, Fowler PA | display-authors = 6 | title = Alternative (backdoor) androgen production and masculinization in the human fetus | journal = PLOS Biology | volume = 17 | issue = 2 | pages = e3000002 | date = February 2019 | pmid = 30763313 | pmc = 6375548 | doi = 10.1371/journal.pbio.3000002 | doi-access = free }}</ref><ref name="pmid23073980">{{cite journal | vauthors = Fukami M, Homma K, Hasegawa T, Ogata T | title = Backdoor pathway for dihydrotestosterone biosynthesis: implications for normal and abnormal human sex development | journal = Developmental Dynamics | volume = 242 | issue = 4 | pages = 320–329 | date = April 2013 | pmid = 23073980 | doi = 10.1002/dvdy.23892 | s2cid = 44702659 | doi-access = free }}</ref><ref name="pmid30943210">{{cite journal | vauthors = Miller WL, Auchus RJ | title = The "backdoor pathway" of androgen synthesis in human male sexual development | journal = PLOS Biology | volume = 17 | issue = 4 | pages = e3000198 | date = April 2019 | pmid = 30943210 | pmc = 6464227 | doi = 10.1371/journal.pbio.3000198 | doi-access = free }}</ref>

==Biosynthesis==
5α-Pregnane-3α,17α-diol-20-one is produced from [[Chemistry:5α-Pregnan-17α-ol-3,20-dione|5α-pregnan-17α-ol-3,20-dione]]<ref name="pmid31533357">{{cite journal | vauthors = Baronio F, Ortolano R, Menabò S, Cassio A, Baldazzi L, Di Natale V, Tonti G, Vestrucci B, Balsamo A | display-authors = 6 | title = 46,XX DSD due to Androgen Excess in Monogenic Disorders of Steroidogenesis: Genetic, Biochemical, and Clinical Features | journal = International Journal of Molecular Sciences | volume = 20 | issue = 18 | page = 4605 | date = September 2019 | pmid = 31533357 | pmc = 6769793 | doi = 10.3390/ijms20184605 | doi-access = free }}</ref> in a reaction catalyzed by a reductive [[Biology:3α-Hydroxysteroid dehydrogenase|3α-hydroxysteroid dehydrogenase]] (3α-HSD),<ref name="pmid21030877">{{cite journal | vauthors = Sharifi N, McPhaul MJ, Auchus RJ | title = "Getting from here to there"--mechanisms and limitations to the activation of the androgen receptor in castration-resistant prostate cancer | journal = Journal of Investigative Medicine | volume = 58 | issue = 8 | pages = 938–944 | date = December 2010 | pmid = 21030877 | pmc = 5589138 | doi = 10.2310/JIM.0b013e3181ff6bb8 | quote = 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) }}</ref> i.e. by the two aldo-keto reductase isozymes: [[Biology:AKR1C2|AKR1C2]] and AKR1C4,<ref name="pmid22072737"/> and by [[Biology:17β-Hydroxysteroid dehydrogenase|17β-hydroxysteroid dehydrogenase 6]] (HSD17B6) that also has the 3α-HSD activity.<ref name="pmid22072737">{{cite journal | vauthors = Miller WL | title = The syndrome of 17,20 lyase deficiency | journal = The Journal of Clinical Endocrinology and Metabolism | volume = 97 | issue = 1 | pages = 59–67 | date = January 2012 | pmid = 22072737 | pmc = 3251937 | doi = 10.1210/jc.2011-2161 }}</ref>

== See also ==
* [[Biology:Androgen backdoor pathway|Androgen backdoor pathway]]
* [[Chemistry:Pregnane|Pregnane]]
* 5α-Pregnane
* [[Chemistry:Allopregnane|Allopregnane]]
* [[Biology:Allopregnanolone|Allopregnanolone]]
* [[Chemistry:5α-Pregnan-17α-ol-3,20-dione|5α-Pregnan-17α-ol-3,20-dione]]
* 5α-Dihydrotestosterone

== References ==
{{Reflist}}

{{Endogenous steroids}}

{{DEFAULTSORT:Pregnane-3α, 17α-diol-20-one, 5α-}}
[[Category:Pregnanes]]
[[Category:Human metabolites]]



{{Sourceattribution|5α-Pregnane-3α,17α-diol-20-one}}