Structure Database (LMSD)

Common Name
alpha-androstenol
Systematic Name
androst-16-en-3α-ol
Synonyms
  • 5alpha-Androst-16-en-3alpha-ol
LM ID
LMST02020008
Formula
Exact Mass
Calculate m/z
274.229666
Sum Composition
Status
Curated


Classification

Biological Context

5α-Androst-16-en-3α-ol is a steroid pheromone that has been found in boar testes and human male axillary sweat and has diverse biological activities.1,2 It enhances GABA-activated currents in primary mouse cerebellar granule cells (EC50 = 0.4 µM).2 5α-Androst-16-en-3α-ol (0.1-1 µM) increases the amplitude of GABA-activated currents in HEK293 cells expressing human α1β2γ2 and α2β2γ2 subunit-containing GABAA receptors. In vivo, 5α-androst-16-en-3α-ol (5-10 mg/kg) decreases immobility time in the forced swim test in mice. It increases time spent in the open arms of the elevated plus maze in mice, indicating anxiolytic-like activity, when administered at doses ranging from 30 to 50 mg/kg. 5α-Androst-16-en-3α-ol protects against seizures induced by pentylenetetrazole (PTZ) or electroshock in mice (ED50s = 48.9 and 21.9 mg/kg, respectively).

This information has been provided by Cayman Chemical

References

1. Brooksbank, B.W., Brown, R., and Gustafsson, J.A. The detection of 5α-androst-16-en-3α-ol in human male axillary sweat. Experientia 30(8), 864-865 (1974).
2. Kaminski, R.M., Marini, H., Ortinski, P.I., et al. The pheromone androstenol (5α-androst-16-en-3α-ol) is a neurosteroid positive modulator of GABAA receptors. J. Pharmacol. Exp. Ther. 317(2), 694-703 (2006).

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Homo sapiens (#9606)
Mammalia (#40674)
The detection of 5alpha-androst-16-en-3alpha-ol in human male axillary sweat.,
Experientia, 1974
Pubmed ID: 4416149

String Representations

InChiKey (Click to copy)
KRVXMNNRSSQZJP-PHFHYRSDSA-N
InChi (Click to copy)
InChI=1S/C19H30O/c1-18-9-3-4-16(18)15-6-5-13-12-14(20)7-11-19(13,2)17(15)8-10-18/h3,9,13-17,20H,4-8,10-12H2,1-2H3/t13-,14+,15-,16-,17-,18-,19-/m0/s1
SMILES (Click to copy)
C1[C@]2(C)[C@@]3([H])CC[C@]4(C)C=CC[C@@]4([H])[C@]3([H])CC[C@@]2([H])C[C@H](O)C1

Other Databases

Wikipedia
HMDB ID
CHEBI ID
LIPIDBANK ID
SST0029
PubChem CID
Cayman ID
PDB ID
GuidePharm ID

Calculated Physicochemical Properties

Heavy Atoms 20
Rings 4
Aromatic Rings 0
Rotatable Bonds 0
Van der Waals Molecular Volume 293.97
Topological Polar Surface Area 20.23
Hydrogen Bond Donors 1
Hydrogen Bond Acceptors 1
logP 4.84
Molar Refractivity 82.77

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Created at
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Updated at
10th Feb 2025