Structure via PubChem · Public domain (PubChem)
4-androstenediol
Sign in to saveAlso known as Androst-4-ene-3beta,17beta-diol, androst-4-ene-3β,17β-diol
4-Androstenediol, also known as androst-4-ene-3β,17β-diol, is an androstenediol that is converted to testosterone. The conversion rate is about 15.76%, almost triple that of 4-androstenedione, due to utilization of a different enzymatic pathway. There is also some conversion into estrogen, since testosterone is the metabolic precursor of the estrogens.
Chemical data
- Formula
- C19H30O2
- Molecular weight
- 290.4 g/mol
- IUPAC name
- (3S,8R,9S,10R,13S,14S,17S)-10,13-dimethyl-2,3,6,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-3,17-diol
- SMILES
- C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2O)CCC4=C[C@H](CC[C@]34C)O
- InChIKey
- BTTWKVFKBPAFDK-LOVVWNRFSA-N
- XLogP
- 3.4
- Polar surface area
- 40.5 Ų
- H-bond donors
- 2
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Wikidata facts
- Mass
- 290.22458
Show 5 more facts
- chemical formula
- C₁₉H₃₀O₂
- isomeric SMILES
- C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2O)CCC4=C[C@H](CC[C@]34C)O
- canonical SMILES
- CC12CCC3C(C1CCC2O)CCC4=CC(CCC34C)O
- Commons category
- 4-Androstenediol
- found in taxon
- Homo sapiens
via Wikidata · CC0
~1 min read
Encyclopedic overview
2 sectionsContents
- Medical and commercial use
- References
4-Androstenediol, also known as androst-4-ene-3β,17β-diol, is an androstenediol that is converted to testosterone. The conversion rate is about 15.76%, almost triple that of 4-androstenedione, due to utilization of a different enzymatic pathway. There is also some conversion into estrogen, since testosterone is the metabolic precursor of the estrogens.
4-Androstenediol is closer to testosterone structurally than 5-androstenediol, and has androgenic effects, acting as a weak partial agonist of the androgen receptor. However, due to its lower intrinsic activity in comparison, in the presence of full agonists like testosterone or dihydrotestosterone (DHT), 4-androstenediol has antagonistic actions, behaving more like an antiandrogen.
Excerpted from Wikipedia’s “4-androstenediol” article, available under the CC BY-SA 4.0 licence.