Structure via PubChem · Public domain (PubChem)
epiandrosterone
Sign in to saveAlso known as Isoandrosterone, 3-Epiandrosterone, d-Epiandrosterone, iso-Androsterone, 3beta-Hydroxyetioallocholan-17-one, trans-Androsterone, (1S,2S,5S,10R,11S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-one, 3b-Hydroxy-5a-androstan-17-one
Epiandrosterone, or isoandrosterone, also known as 3β-androsterone, 3β-hydroxy-5α-androstan-17-one, or 5α-androstan-3β-ol-17-one, is a steroid hormone with weak androgenic activity. It is a metabolite of testosterone and dihydrotestosterone (DHT). It was first isolated in 1931, by Adolf Friedrich Johann Butenandt and Kurt Tscherning. They distilled over 17,000 litres of male urine, from which they got 50 milligrams of crystalline androsterone (most likely mixed isomers), which was sufficient to find that the chemical formula was very similar to estrone.
Chemical data
- Formula
- C19H30O2
- Molecular weight
- 290.4 g/mol
- IUPAC name
- (3S,5S,8R,9S,10S,13S,14S)-3-hydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthren-17-one
- SMILES
- C[C@]12CC[C@@H](C[C@@H]1CC[C@@H]3[C@@H]2CC[C@]4([C@H]3CCC4=O)C)O
- InChIKey
- QGXBDMJGAMFCBF-LUJOEAJASA-N
- XLogP
- 3.7
- Polar surface area
- 37.3 Ų
- H-bond donors
- 1
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Wikidata facts
- Subclass of
- steroid
- Mass
- 290.225
Show 5 more facts
- stereoisomer of
- androsterone
- chemical formula
- C₁₉H₃₀O₂
- canonical SMILES
- CC12CCC(CC1CCC3C2CCC4(C3CCC4=O)C)O
- isomeric SMILES
- C[C@]12CC[C@@H](C[C@@H]1CC[C@@H]3[C@@H]2CC[C@]4([C@H]3CCC4=O)C)O
- Commons category
- Epiandrosterone
via Wikidata · CC0
~1 min read
Encyclopedic overview
4 sectionsContents
- Applications
- See also
- References
- Further reading
Epiandrosterone, or isoandrosterone, also known as 3β-androsterone, 3β-hydroxy-5α-androstan-17-one, or 5α-androstan-3β-ol-17-one, is a steroid hormone with weak androgenic activity. It is a metabolite of testosterone and dihydrotestosterone (DHT). It was first isolated in 1931, by Adolf Friedrich Johann Butenandt and Kurt Tscherning. They distilled over 17,000 litres of male urine, from which they got 50 milligrams of crystalline androsterone (most likely mixed isomers), which was sufficient to find that the chemical formula was very similar to estrone.
Epiandrosterone has been shown to naturally occur in most mammals including pigs.
Excerpted from Wikipedia’s “epiandrosterone” article, available under the CC BY-SA 4.0 licence.