Structure via PubChem · Public domain (PubChem)
11-deoxycortisol
Sign in to saveAlso known as cortodoxone, (2R,10R,14R,15S)-14-hydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one, 17-Hydroxy-11-deoxycorticosterone, 11-Deoxy-17-hydroxy-Corticosterone, Reichstein'S substance S, 11-Dioxy-Cortisol, Reichstein'S compound S, 11-Deoxy-17-hydroxycorticosterone
11-Deoxycortisol, also known as cortodoxone (INN), cortexolone as well as 17α,21-dihydroxyprogesterone or 17α,21-dihydroxypregn-4-ene-3,20-dione, is an endogenous glucocorticoid steroid hormone, and a metabolic intermediate toward cortisol. It was first described by Tadeusz Reichstein in 1938 as Substance S, thus has also been referred to as '''Reichstein's Substance S or Compound S'''.
Chemical data
- Formula
- C21H30O4
- Molecular weight
- 346.5 g/mol
- IUPAC name
- (8R,9S,10R,13S,14S,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-3-one
- SMILES
- C[C@]12CCC(=O)C=C1CC[C@@H]3[C@@H]2CC[C@]4([C@H]3CC[C@@]4(C(=O)CO)O)C
- InChIKey
- WHBHBVVOGNECLV-OBQKJFGGSA-N
- XLogP
- 2.5
- Polar surface area
- 74.6 Ų
- H-bond donors
- 2
- H-bond acceptors
- 4
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Phase 2
- Molecule type
- Small molecule
via ChEMBL · EBI
Research
1,684 papers- 11-deoxycortisol positively correlates with T cell immune traits in physiological conditions.EBioMedicine · 2024
- [11-Deoxycortisol].Nihon rinsho. Japanese journal of clinical medicine · 2005
- [11-Deoxycortisol].Nihon rinsho. Japanese journal of clinical medicine · 1995
- [11-deoxycortisol and 21-deoxycortisol].Nihon rinsho. Japanese journal of clinical medicine · 1999
- 11-deoxycortisol is a corticosteroid hormone in the lamprey.Proceedings of the National Academy of Sciences of the United States of America · 2010
via PubMed
Wikidata facts
- Has part
- carbon
- Mass
- 346.214409
- Has use
- medication
Show 7 more facts
- chemical formula
- C₂₁H₃₀O₄
- canonical SMILES
- CC12CCC(=O)C=C1CCC3C2CCC4(C3CCC4(C(=O)CO)O)C
- isomeric SMILES
- C[C@]12CCC(=O)C=C1CC[C@@H]3[C@@H]2CC[C@]4([C@H]3CC[C@@]4(C(=O)CO)O)C
- found in taxon
- Homo sapiens
- Commons category
- Cortodoxone
- melting point
- 208
- subject has role
- primary metabolite
via Wikidata · CC0
~8 min read
Encyclopedic overview
5 sectionsContents
- Function
- Clinical significance
- History
- See also
- References
11-Deoxycortisol, also known as cortodoxone (INN), cortexolone as well as 17α,21-dihydroxyprogesterone or 17α,21-dihydroxypregn-4-ene-3,20-dione, is an endogenous glucocorticoid steroid hormone, and a metabolic intermediate toward cortisol. It was first described by Tadeusz Reichstein in 1938 as Substance S, thus has also been referred to as '''Reichstein's Substance S or Compound S'''.
==Function== thumb|left|class=skin-invert-image|Steroidogenesis, showing 11-deoxycortisol in the pathway from [[cholesterol to cortisol.]]
Excerpted from Wikipedia’s “11-deoxycortisol” article, available under the CC BY-SA 4.0 licence.
Gallery (2)
Available in 10 languages
via Wikidata sitelinks · CC0