Tetrahydrocortisol

Tetrahydrocortisol, or urocortisol, also known as 3α,11β,17α,21-tetrahydroxy-5β-pregnan-20-one, is a steroid and an inactive metabolite of cortisol.[1]

Tetrahydrocortisol
Names
IUPAC name
3α,11β,17,21-Tetrahydroxy-5β-pregnan-20-one
Systematic IUPAC name
2-Hydroxy-1-(1R,3aS,3bS,5aR,7R,9aS,9bS,10S,11aS)-1,7,10-trihydroxy-9a,11a-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-1-yl]ethan-1-one
Other names
Urocortisol; 3α,5β-Tetrahydrocortisol; 3α,5β-Cortisol
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.000.146
UNII
  • InChI=1S/C21H34O5/c1-19-7-5-13(23)9-12(19)3-4-14-15-6-8-21(26,17(25)11-22)20(15,2)10-16(24)18(14)19/h12-16,18,22-24,26H,3-11H2,1-2H3/t12-,13-,14+,15+,16+,18-,19+,20+,21+/m1/s1 checkY
    Key: AODPIQQILQLWGS-GXBDJPPSSA-N checkY
  • InChI=1/C21H34O5/c1-19-7-5-13(23)9-12(19)3-4-14-15-6-8-21(26,17(25)11-22)20(15,2)10-16(24)18(14)19/h12-16,18,22-24,26H,3-11H2,1-2H3/t12-,13-,14+,15+,16+,18-,19+,20+,21+/m1/s1
    Key: AODPIQQILQLWGS-GXBDJPPSBG
  • O=C(CO)[C@@]4(O)CC[C@H]3[C@H]2[C@@H]([C@@]1([C@@H](C[C@H](O)CC1)CC2)C)[C@@H](O)C[C@@]34C
Properties
C21H34O5
Molar mass 366.49 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Infobox references

Tetrahydrocortisol is a neurosteroid and has been found to act as a negative allosteric modulator of the GABAA receptor, similarly to pregnenolone sulfate.[2][3][4]

See also

References
  1. Thomas L. Lemke; David A. Williams (24 January 2012). Foye's Principles of Medicinal Chemistry. Lippincott Williams & Wilkins. pp. 915–. ISBN 978-1-60913-345-0.
  2. Nikolaou N, Hodson L, Tomlinson JW (March 2021). "The role of 5-reduction in physiology and metabolic disease: evidence from cellular, pre-clinical and human studies". J Steroid Biochem Mol Biol. 207: 105808. doi:10.1016/j.jsbmb.2021.105808. PMID 33418075.
  3. Chen M, Penning TM (May 2014). "5β-Reduced steroids and human Δ(4)-3-ketosteroid 5β-reductase (AKR1D1)". Steroids. 83: 17–26. doi:10.1016/j.steroids.2014.01.013. PMC 3971473. PMID 24513054.
  4. Penland SN, Morrow AL (December 2004). "3alpha,5beta-Reduced cortisol exhibits antagonist properties on cerebral cortical GABA(A) receptors". Eur J Pharmacol. 506 (2): 129–32. doi:10.1016/j.ejphar.2004.11.007. PMID 15588732.


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