Tetrahydrocortisol
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Names | |
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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 | |
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3D model (JSmol) |
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ChEBI |
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ChemSpider |
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ECHA InfoCard | 100.000.146 ![]() |
PubChem CID |
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CompTox Dashboard (EPA) |
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InChI
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Properties | |
Chemical formula | 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). ![]() ![]() ![]() Infobox references |
Chemical compound
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 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
- ^ 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.
- ^ 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. S2CID 230716310.
- ^ 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.
- ^ 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.
- v
- t
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- Cholesterol
- 22R-Hydroxycholesterol
- 20α,22R-Dihydroxycholesterol
- Pregnenolone
- 11β-Hydroxypregnenolone
- 17α-Hydroxypregnenolone
- 21-Hydroxypregnenolone
- 17α,21-Dihydroxypregnenolone
- 11β,17α,21-Trihydroxypregnenolone
- Cholestanes: 24S-Hydroxycholesterol
- Cholesterol
- Pregnanes: 3α-Dihydroprogesterone
- 3β-Dihydroprogesterone
- 5α-Dihydrocorticosterone
- 5α-Dihydroprogesterone
- 5β-Dihydroprogesterone
- Allopregnanolone
- Corticosterone
- DHC
- DHDOC
- 11-Deoxycorticosterone
- Epipregnanolone
- Isopregnanolone
- Pregnanolone
- Pregnenolone
- Pregnenolone sulfate
- Progesterone
- THB
- THDOC
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