Structure via PubChem · Public domain (PubChem)
tetrahydrocortisol
Sign in to saveAlso known as 3alpha,5beta-Tetrahydrocortisol, 5beta-Tetrahydrocortisol, Tetrahydrohydrocortisone, Tetrahydro-cortisol, 2-hydroxy-1-[(2S,5R,14R,15S,17S)-5,14,17-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]ethan-1-one, Dihydrocortison, Urocortisol
Tetrahydrocortisol, or urocortisol, also known as 3α,11β,17α,21-tetrahydroxy-5β-pregnan-20-one, is a steroid and an inactive metabolite of cortisol.
Chemical data
- Formula
- C21H34O5
- Molecular weight
- 366.5 g/mol
- IUPAC name
- 2-hydroxy-1-[(3R,5R,8S,9S,10S,11S,13S,14S,17R)-3,11,17-trihydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthren-17-yl]ethanone
- SMILES
- C[C@]12CC[C@H](C[C@H]1CC[C@@H]3[C@@H]2[C@H](C[C@]4([C@H]3CC[C@@]4(C(=O)CO)O)C)O)O
- InChIKey
- AODPIQQILQLWGS-GXBDJPPSSA-N
- XLogP
- 2.5
- Polar surface area
- 98 Ų
- H-bond donors
- 4
- H-bond acceptors
- 5
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Research
534 papers- A radioimmunoassay for tetrahydrocortisol.Analytical biochemistry · 1978
- Tetrahydrocortisol metabolism in man.Steroids · 1968
- Tetrahydrocortisol/tetrahydrocortisone ratio (H4F/H4E) as an indicator of depressive feelings.Psychosomatic medicine · 1976
- Synthesis of tetrahydrocortisol 3-glucuronide.Journal of steroid biochemistry · 1973
- Tetrahydrocortisol-apolipoprotein A-I complex specifically interacts with eukaryotic DNA and GCC elements of genes.The Journal of steroid biochemistry and molecular biology · 2003
via PubMed
Wikidata facts
- Subclass of
- steroid
- Mass
- 366.241
Show 3 more facts
- chemical formula
- C₂₁H₃₄O₅
- canonical SMILES
- CC12CCC(CC1CCC3C2C(CC4(C3CCC4(C(=O)CO)O)C)O)O
- isomeric SMILES
- C[C@]12CC[C@H](C[C@H]1CC[C@@H]3[C@@H]2[C@H](C[C@]4([C@H]3CC[C@@]4(C(=O)CO)O)C)O)O
via Wikidata · CC0
~1 min read
Encyclopedic overview
2 sectionsContents
- See also
- References
Tetrahydrocortisol, or urocortisol, also known as 3α,11β,17α,21-tetrahydroxy-5β-pregnan-20-one, is a steroid and an inactive metabolite of cortisol.
Tetrahydrocortisol is a neurosteroid and has been found to act as a negative allosteric modulator of the GABAA receptor, similarly to pregnenolone sulfate.
Excerpted from Wikipedia’s “tetrahydrocortisol” article, available under the CC BY-SA 4.0 licence.