androsterone

Also known as cis-androsterone, (3alpha,5alpha)-3-hydroxyandrostan-17-one, 5alpha-androsterone, Androtine, Androkinine, 5alpha-androstane-3alpha-ol-17-one, 3-epihydroxyetioallocholan-17-one, (3R,5S,8R,9S,10S,13S,14S)-3-hydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthren-17-one

Androsterone, or 3α-hydroxy-5α-androstan-17-one, is an endogenous steroid hormone, neurosteroid, and putative pheromone. It is a weak androgen with a potency that is approximately 1/7 that of testosterone. Androsterone is a metabolite of testosterone and dihydrotestosterone (DHT). In addition, it can be converted back into DHT via 3α-hydroxysteroid dehydrogenase and 17β-hydroxysteroid dehydrogenase, bypassing conventional intermediates such as androstanedione and testosterone, and as such, can be considered to be a metabolic intermediate in its own right.

Key facts

Drug.PubChem: 5879
Drug.ATC_prefix: none
Drug.ChEMBL: 87285
Drug.verifiedrevid: 457130388
Drug.IUPAC_name: (3R,5S,8R,9S,10S,13S,14S)-3-hydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthren-17-one
Drug.image: androsteron.svg
Drug.image_class: skin-invert-image
Drug.alt: Skeletal formula of androsterone
Drug.width: 210
Drug.image2: Androsterone-3D-balls.png
Drug.image_class2: bg-transparent
Drug.alt2: Ball-and-stick model of the androsterone molecule
Drug.width2: 220
Drug.CAS_number: 53-41-8
Drug.ChemSpiderID: 5668
Drug.UNII: C24W7J5D5R
Drug.synonyms: 3α-hydroxy-5α-androstan-17-one, 5α-androstan-3α-ol-17-one
Drug.ChEBI: 16032

via Wikipedia infobox

Chemical data

Formula: C19H30O2
Molecular weight: 290.4 g/mol
IUPAC name: (3R,5S,8R,9S,10S,13S,14S)-3-hydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthren-17-one
SMILES: C[C@]12CC[C@H](C[C@@H]1CC[C@@H]3[C@@H]2CC[C@]4([C@H]3CCC4=O)C)O
InChIKey: QGXBDMJGAMFCBF-HLUDHZFRSA-N
XLogP: 3.7
Polar surface area: 37.3 Å²
H-bond donors: 1
H-bond acceptors: 2
Formal charge: 0

via PubChem

Research

3,212 papers

[Androsterone].Nihon rinsho. Japanese journal of clinical medicine · 2005
[Androsterone].Nihon rinsho. Japanese journal of clinical medicine · 1999
[Androsterone].Nihon rinsho. Japanese journal of clinical medicine · 1995
Steroid Hormone Androsterone Observed in the Gas Phase by Rotational Spectroscopy.The journal of physical chemistry letters · 2022
Serum androsterone levels in children.Hormone and metabolic research = Hormon- und Stoffwechselforschung = Hormones et metabolisme · 1996

via PubMed

Wikidata facts

Mass: 290.225

Show 4 more facts

chemical formula: C₁₉H₃₀O₂
canonical SMILES: CC12CCC(CC1CCC3C2CCC4(C3CCC4=O)C)O
isomeric SMILES: C[C@]12CC[C@H](C[C@@H]1CC[C@@H]3[C@@H]2CC[C@]4([C@H]3CCC4=O)C)O
Commons category: Androsterone

Sources (3)

via Wikidata · CC0

~5 min read

Article

11 sections

Contents

Biological function
Pheromone
Biochemistry
Biosynthesis
Metabolism
Chemistry
Sources
History
See also
References
External links

Androsterone is also known to be an inhibitory androstane neurosteroid, acting as a positive allosteric modulator of the GABAA receptor, and possesses anticonvulsant effects. The unnatural enantiomer of androsterone is more potent as a positive allosteric modulator of GABAA receptors and as an anticonvulsant than the natural form. Androsterone's 3β-isomer is epiandrosterone, and its 5β-epimer is etiocholanolone. The 3β,5β-isomer is epietiocholanolone.