Structure via PubChem · Public domain (PubChem)
androstenediol
Sign in to saveAlso known as 5-andendiol, 5-androstenediol, androst-5-ene-3beta,17beta-diol, androst-5-enediol, hermaphrodiol, 3beta,17beta-Dihydroxy-5-androstene, 3beta,17beta-Dihydroxyandrost-5-ene, (3beta,17beta)-androst-5-ene-3,17-diol
Androstenediol, or 5-androstenediol (abbreviated as A5 or Δ5-diol), also known as androst-5-ene-3β,17β-diol, is an endogenous weak androgen and estrogen steroid hormone and intermediate in the biosynthesis of testosterone from dehydroepiandrosterone (DHEA). It is closely related to androstenedione (androst-4-ene-3,17-dione).
In the Vinony graph
Within Vinony's link graph, androstenediol is referenced by 1,233 other articles, and connects out to ligand, DDT and androstenedione.
It sits within the topics Androgens, Androstanes and Drugs missing an ATC code.
Its subject is documented across 11 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-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-3,17-diol
- SMILES
- C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2O)CC=C4[C@@]3(CC[C@@H](C4)O)C
- InChIKey
- QADHLRWLCPCEKT-LOVVWNRFSA-N
- XLogP
- 3.5
- 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
Research
746 papers- The potential value of 5-androstenediol in countering acute radiation syndrome.Drug discovery today · 2024
- Dehydroepiandrosterone and Its Metabolite 5-Androstenediol: New Therapeutic Targets and Possibilities for Clinical Application.Pharmaceuticals (Basel, Switzerland) · 2024
- 17α-androstenediol-mediated oncophagy of tumor cells by different mechanisms is determined by the target tumor.Annals of the New York Academy of Sciences · 2012
- Androstenediol analogs as ER-beta-selective SERMs.Bioorganic & medicinal chemistry letters · 2006
- Androstenediol reverses steroid-inhibited wound healing.Wound repair and regeneration : official publication of the Wound Healing Society [and] the European Tissue Repair Society · 2009
via PubMed
Wikidata facts
- Mass
- 290.225
Show 5 more facts
- chemical formula
- C₁₉H₃₀O₂
- canonical SMILES
- CC12CCC3C(C1CCC2O)CC=C4C3(CCC(C4)O)C
- isomeric SMILES
- C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2O)CC=C4[C@@]3(CC[C@@H](C4)O)C
- found in taxon
- Homo sapiens
- Commons category
- 5-Androstenediol
via Wikidata · CC0
~4 min read
Encyclopedic overview
8 sectionsContents
- Biological activity
- Chemistry
- Synthesis
- Esters
- Research
- Radiation countermeasure
- Additional images
- References
Androstenediol, or 5-androstenediol (abbreviated as A5 or Δ5-diol), also known as androst-5-ene-3β,17β-diol, is an endogenous weak androgen and estrogen steroid hormone and intermediate in the biosynthesis of testosterone from dehydroepiandrosterone (DHEA). It is closely related to androstenedione (androst-4-ene-3,17-dione).
==Biological activity== Androstenediol is a direct metabolite of the most abundant steroid produced by the human adrenal cortex, DHEA. It is less androgenic than the related compound, Δ4-androstenediol, and has been found to stimulate the immune system. When administered to rats, androstenediol, in vivo, has approximately 1.4% of the androgenicity of DHEA, 0.54% of the androgenicity of androstenedione, and 0.21% of the androgenicity of testosterone.
Excerpted from Wikipedia’s “androstenediol” article, available under the CC BY-SA 4.0 licence.