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Details

Stereochemistry ABSOLUTE
Molecular Formula C19H28O
Molecular Weight 272.425
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 6
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 5.ALPHA.-ANDROST-16-EN-3-ONE

SMILES

[H][C@@]12CC=C[C@@]1(C)CC[C@@]3([H])[C@@]2([H])CC[C@@]4([H])CC(=O)CC[C@]34C

InChI

InChIKey=HFVMLYAGWXSTQI-QYXZOKGRSA-N
InChI=1S/C19H28O/c1-18-9-3-4-16(18)15-6-5-13-12-14(20)7-11-19(13,2)17(15)8-10-18/h3,9,13,15-17H,4-8,10-12H2,1-2H3/t13-,15-,16-,17-,18-,19-/m0/s1

HIDE SMILES / InChI

Molecular Formula C19H28O
Molecular Weight 272.425
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 6 / 6
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

The compound believed to be principally responsible for the unpleasant odor sometimes produced during cooking of pork or bacon from boars has been isolated and identified as 5a-androst-16-en-3-one. It is the first mammalian pheromone to be identified. Androstenone is the active ingredient in a commercial products which were developed for farmers and breeders who need help determining the best fertilization time for sows and gilts. In humans, androstenone also has been suggested to be a pheromone. Excessive exposures may affect human health, as follows: Upper respiratory tract: Irritation, Dizziness, Drowsiness, Headache, Nausea; Skin: Redness.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
30.0 µM [EC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
Boarmate

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
Spray product at the gilt or sows snout for two seconds from a distance of approximately 60 centimetres, then apply pressure to the back of the sow (the „back pressure“ test).
Route of Administration: Irrigation
In Vitro Use Guide
Analysis of receptor binding of 5alpha-androst-16-en-3-one gave a value for the affinity constant (Ka) of approx. 8.3-10(8) M-1 and the value for the molar concentration of binding sites (n[M]) was approx. 3.3 pmol/mg protein.
Substance Class Chemical
Record UNII
BWD3D5941J
Record Status Validated (UNII)
Record Version