Structure via PubChem · Public domain (PubChem)
androstadienone
Sign in to saveAndrostadienone, 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.
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 Ų
- 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
via Wikidata · CC0
~1 min read
Encyclopedic overview
3 sectionsContents
- See also
- References
- Further reading
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.
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.
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via Wikidata sitelinks · CC0