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.
In the Vinony graph
Vinony's link graph records 958 inbound references to 4-androstenediol, and connects out to DDT, androstenediol and (+)-catechin.
It sits within the topics Androgen esters, Androgens and Androstanes.
Vinony links it to 9 Wikipedia language editions.
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.