Structure via PubChem · Public domain (PubChem)
tetrahydrocortisone
Sign in to saveAlso known as Urocortisone, 3alpha,17,21-trihydroxy-5beta-Pregnane-11,20-dione, 3alpha,17,21-Trihydroxypregnane-11,20-dione, Tetrahydrocortison, 3,17-Dihydroxy-17-hydroxyacetyl-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-11-one, Tetrahydro E, 3a,17,21-Trihydroxy-5b-pregnane-11,20-dione, 3b,17,21-Trihydroxy-5a-pregnane-11,20-dione
Tetrahydrocortisone, or urocortisone, also known as 3α,17α,21-trihydroxy-5β-pregnane-11,20-dione, is a steroid and an inactive metabolite of cortisone.
Chemical data
- Formula
- C21H32O5
- Molecular weight
- 364.5 g/mol
- IUPAC name
- (3R,5R,8S,9S,10S,13S,14S,17R)-3,17-dihydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-2,3,4,5,6,7,8,9,12,14,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-11-one
- SMILES
- C[C@]12CC[C@H](C[C@H]1CC[C@@H]3[C@@H]2C(=O)C[C@]4([C@H]3CC[C@@]4(C(=O)CO)O)C)O
- InChIKey
- SYGWGHVTLUBCEM-ZIZPXRJBSA-N
- XLogP
- 2.2
- Polar surface area
- 94.8 Ų
- H-bond donors
- 3
- H-bond acceptors
- 5
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Research
428 papers- Tetrahydrocortisol/tetrahydrocortisone ratio (H4F/H4E) as an indicator of depressive feelings.Psychosomatic medicine · 1976
- Metabolism of tetrahydrocortisone in health and disease.The Journal of clinical endocrinology and metabolism · 1968
- Determination of urinary tetrahydrocortisone tetrahydrocortisol and 3-alpha-allotetrahydrocortisol by gas chromatography.Steroids · 1965
- Synthesis of deuterium-labeled tetrahydrocortisol and tetrahydrocortisone for study of cortisol metabolism in humans.Steroids · 1999
- Determination of tetrahydrocortisol and tetrahydrocortisone in the urine of normal and schizophrenic men.The Journal of clinical endocrinology and metabolism · 1957
via PubMed
Wikidata facts
- Mass
- 364.225
Show 3 more facts
- chemical formula
- C₂₁H₃₂O₅
- canonical SMILES
- CC12CCC(CC1CCC3C2C(=O)CC4(C3CCC4(C(=O)CO)O)C)O
- isomeric SMILES
- C[C@]12CC[C@H](C[C@H]1CC[C@@H]3[C@@H]2C(=O)C[C@]4([C@H]3CC[C@@]4(C(=O)CO)O)C)O
via Wikidata · CC0
~1 min read
Encyclopedic overview
2 sectionsContents
- See also
- References
Tetrahydrocortisone, or urocortisone, also known as 3α,17α,21-trihydroxy-5β-pregnane-11,20-dione, is a steroid and an inactive metabolite of cortisone.
==See also== Tetrahydrocortisol Tetrahydrocorticosterone
Excerpted from Wikipedia’s “tetrahydrocortisone” article, available under the CC BY-SA 4.0 licence.