Structure via PubChem · Public domain (PubChem)
3β-androstanediol
Sign in to saveAlso known as 3beta,17beta-dihydroxy-5alpha-androstane, (3beta,5alpha,17beta)-androstane-3,17-diol, 3b,17b-Dihydroxy-5a-androstane, 5alpha-Androstane-3beta,17beta-diol, 3b,17b-Androstanediol, 5alpha-Androstan-3beta,17beta-diol, (1S,2S,5S,7S,10R,11S,14S,15S)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-5,14-diol, 5-Alpha-Androstane-3-Beta,17beta-Diol
3β-Androstanediol, also known as 5α-androstane-3β,17β-diol, and sometimes shortened in the literature to 3β-diol, is an endogenous steroid hormone and a metabolite of androgens like dehydroepiandrosterone (DHEA) and dihydrotestosterone (DHT).
Chemical data
- Formula
- C19H32O2
- Molecular weight
- 292.5 g/mol
- IUPAC name
- (3S,5S,8R,9S,10S,13S,14S,17S)-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3,17-diol
- SMILES
- C[C@]12CC[C@@H](C[C@@H]1CC[C@@H]3[C@@H]2CC[C@]4([C@H]3CC[C@@H]4O)C)O
- InChIKey
- CBMYJHIOYJEBSB-YSZCXEEOSA-N
- XLogP
- 4.2
- 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
- 292.24
Show 4 more facts
- chemical formula
- C₁₉H₃₂O₂
- canonical SMILES
- CC12CCC(CC1CCC3C2CCC4(C3CCC4O)C)O
- isomeric SMILES
- C[C@]12CC[C@@H](C[C@@H]1CC[C@@H]3[C@@H]2CC[C@]4([C@H]3CC[C@@H]4O)C)O
- found in taxon
- Daphnia magna
via Wikidata · CC0
~3 min read
Encyclopedic overview
4 sectionsContents
- Biological activity
- Biochemistry
- Chemistry
- References
3β-Androstanediol, also known as 5α-androstane-3β,17β-diol, and sometimes shortened in the literature to 3β-diol, is an endogenous steroid hormone and a metabolite of androgens like dehydroepiandrosterone (DHEA) and dihydrotestosterone (DHT).
==Biological activity== 3β-Androstanediol is a selective, high-affinity agonist of the ERβ, and hence, an estrogen. In contrast to ERβ, 3β-androstanediol does not bind to the androgen receptor (AR). 3β-Androstanediol has been reported to also bind to ERα with low nanomolar affinity, with several-fold lower affinity relative to ERβ. It has approximately 3% and 7% of the affinity of estradiol at the ERα and ERβ, respectively. Unlike 3α-androstanediol, 3β-androstanediol does not bind to the GABAA receptor.
Excerpted from Wikipedia’s “3β-androstanediol” article, available under the CC BY-SA 4.0 licence.