androstadienone

Androstadienone, or androsta-4,16-dien-3-one, is a 16-androstene class endogenous steroid that has been described as having potent pheromone-like activities in humans. The compound is synthesized from androstadienol by 3β-hydroxysteroid dehydrogenase, and can be converted into androstenone (a more potent and odorous pheromone) by 5α-reductase, which can subsequently be converted into 3α-androstenol or 3β-androstenol (also more potent and odorous pheromones) by 3-ketosteroid reductase.

In the Vinony graph

Within Vinony's link graph, androstadienone is referenced by 199 other articles, and connects out to sex steroid, androstenedione and androstenediol.

It is catalogued under topics including Androstanes, Chemical pages without DrugBank identifier and Cyclopentenes.

Its subject is documented across 9 Wikipedia language editions.

Key facts

Drug.Verifiedfields: changed
Drug.Watchedfields: changed
Drug.verifiedrevid: 438860644
Drug.IUPAC_name: (8S,9S,10R,13R,14S)-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15-decahydrocyclopenta[a]phenanthren-3-one
Drug.image: Androstadienone chemical structure.png
Drug.image_class: skin-invert-image
Drug.width: 200px
Drug.image2: Androstadienone-based-on-xtal-3D-bs-17.png
Drug.image_class2: bg-transparent
Drug.CAS_number: 4075-07-4
Drug.UNII: ZUZ4FHD36E
Drug.ATC_prefix: none
Drug.PubChem: 92979
Drug.ChemSpiderID: 83932
Drug.C: 19
Drug.H: 26
Drug.O: 1
Drug.smiles: C[C@]12CC[C@H]3[C@H]([C@@H]1CC=C2)CCC4=CC(=O)CC[C@]34C

via Wikipedia infobox

Chemical data

Formula: C19H26O
Molecular weight: 270.4 g/mol
IUPAC name: (8S,9S,10R,13R,14S)-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15-decahydrocyclopenta[a]phenanthren-3-one
SMILES: C[C@]12CC[C@H]3[C@H]([C@@H]1CC=C2)CCC4=CC(=O)CC[C@]34C
InChIKey: HNDHDMOSWUAEAW-VMXHOPILSA-N
XLogP: 4.5
Polar surface area: 17.1 Å²
H-bond donors: 0
H-bond acceptors: 1
Formal charge: 0

via PubChem

Wikidata facts

Mass: 270.198

Show 4 more facts

chemical formula: C₁₉H₂₆O
canonical SMILES: CC12CCC3C(C1CC=C2)CCC4=CC(=O)CCC34C
isomeric SMILES: C[C@]12CC[C@H]3[C@H]([C@@H]1CC=C2)CCC4=CC(=O)CC[C@]34C
Commons category: Androstadienone

Sources (3)

via Wikidata · CC0

~1 min read

Encyclopedic overview

3 sections

Contents

See also
References
Further reading

Androstadienone is related to the androgen sex hormones; however, androstadienone does not exhibit any androgenic or anabolic effects. Though it has been reported to significantly affect the mood of heterosexual women and homosexual men, it does not alter behavior overtly, although it may have more subtle effects on attention.

Excerpted from Wikipedia’s “androstadienone” article, available under the CC BY-SA 4.0 licence.