Structure via PubChem · Public domain (PubChem)
androstenedione
Sign in to saveAlso known as androst-4-ene-3,17-dione, Delta(4)-androstene-3,17-dione, Delta(4)-androsten-3,17-dione, Fecundin, 4-Androsten-3,17-dione, Androstendione, [4-14C]androst-4-ene-3,17-dione, (1S,2R,10R,11S,15S)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-ene-5,14-dione
Androstenedione, or 4-androstenedione (abbreviated as A4 or Δ4-dione), also known as androst-4-ene-3,17-dione, is an endogenous weak androgen steroid hormone and intermediate in the biosynthesis of estrone and of testosterone from dehydroepiandrosterone (DHEA). It is closely related to androstenediol (androst-5-ene-3β,17β-diol).
Chemical data
- Formula
- C19H26O2
- Molecular weight
- 286.4 g/mol
- IUPAC name
- (8R,9S,10R,13S,14S)-10,13-dimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene-3,17-dione
- SMILES
- C[C@]12CCC(=O)C=C1CC[C@@H]3[C@@H]2CC[C@]4([C@H]3CCC4=O)C
- InChIKey
- AEMFNILZOJDQLW-QAGGRKNESA-N
- XLogP
- 2.7
- Polar surface area
- 34.1 Ų
- H-bond donors
- 0
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Research
13,042 papers- Androstenedione (a Natural Steroid and a Drug Supplement): A Comprehensive Review of Its Consumption, Metabolism, Health Effects, and Toxicity with Sex Differences.Molecules (Basel, Switzerland) · 2021
- [Androstenedione].Nihon rinsho. Japanese journal of clinical medicine · 2005
- [Androstenedione].Nihon rinsho. Japanese journal of clinical medicine · 1999
- [Androstenedione].Nihon rinsho. Japanese journal of clinical medicine · 1995
- Androstenedione production by biotransformation of phytosterols.Bioresource technology · 2008
via PubMed
Wikidata facts
- Has part
- carbon
- Mass
- 286.193
Show 8 more facts
- chemical formula
- C₁₉H₂₆O₂
- isomeric SMILES
- C[C@]12CCC(=O)C=C1CC[C@@H]3[C@@H]2CC[C@]4([C@H]3CCC4=O)C
- canonical SMILES
- CC12CCC(=O)C=C1CCC3C2CCC4(C3CCC4=O)C
- medical condition treated
- muscle weakness
- found in taxon
- Daphnia magna
- different from
- androstane-3,17-dione
- subject has role
- androgen
- Commons category
- 4-Androstenedione
Sources (6)
via Wikidata · CC0
~9 min read
Encyclopedic overview
14 sectionsContents
- Function
- Adrenarche
- Biochemistry
- Biosynthesis
- Metabolism
- Levels
- Pharmacology
- Medical use
- Chemistry
- History
- Use as a supplement
- Society and culture
- Regulation
- References
Androstenedione, or 4-androstenedione (abbreviated as A4 or Δ4-dione), also known as androst-4-ene-3,17-dione, is an endogenous weak androgen steroid hormone and intermediate in the biosynthesis of estrone and of testosterone from dehydroepiandrosterone (DHEA). It is closely related to androstenediol (androst-5-ene-3β,17β-diol).
== Function == Androstenedione is a precursor of testosterone and other androgens, as well as of estrogens like estrone, in the body. In addition to functioning as an endogenous prohormone, androstenedione also has weak androgenic activity in its own right.
Excerpted from Wikipedia’s “androstenedione” article, available under the CC BY-SA 4.0 licence.