Structure Database (LMSD)

Common Name
Etiocholanolone
Systematic Name
3α-hydroxy-5β-androstan-17-one
Synonyms
  • 5beta-androsterone
LM ID
LMST02020059
Formula
Exact Mass
Calculate m/z
290.22458
Sum Composition
Status
Curated



Classification

Biological Context

Etiocholanolone is an androgenically inactive metabolite of testosterone and androstenedione and the 5β epimer of androsterone .1,2 It increases the frequency of long channel openings and potentiates GABA-induced chloride currents in HEK293 cells expressing rat α1β2γ2L subunit-containing GABAA receptors when used at a concentration of 10 µM.3 Etiocholanolone is protective against seizures induced by 6 Hz electroshock or pentylenetetrazol (PTZ; ED50s = 76.9 and 139 mg/kg, respectively).4 It is also pyretic in an IL-1-dependent manner, inducing increases in body temperature in rhesus macaques but not squirrel monkeys that lack testosterone and androstenedione metabolizing enzymes.5

This information has been provided by Cayman Chemical

References

1. Baulieu, E.-E., and Mauvais-Jarvis, P. Studies on testosterone metabolism. The Journal of Biological Chemisty 239(5), 1569-1577 (1964).

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Homo sapiens (#9606)
Mammalia (#40674)
STUDIES ON TESTOSTERONE METABOLISM. I. CONVERSION OF TESTOSTERONE-17-ALPHA-3H TO 5-ALPHA- AND 5-BETA-ANDROSTANE-3-ALPHA, 17-BETA-DEOL-17-ALPHA-3H: A NEW "17-BETA-HYDROXYL PATHWAY".,
J Biol Chem, 1964
Pubmed ID: 14189896

String Representations

InChiKey (Click to copy)
QGXBDMJGAMFCBF-BNSUEQOYSA-N
InChi (Click to copy)
InChI=1S/C19H30O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h12-16,20H,3-11H2,1-2H3/t12-,13-,14+,15+,16+,18+,19+/m1/s1
SMILES (Click to copy)
[C@@]12([H])CC[C@]3([H])C[C@@H](CC[C@]3(C)[C@@]1([H])CC[C@]1(C)C(CC[C@@]21[H])=O)O

Other Databases

Wikipedia
KEGG ID
HMDB ID
CHEBI ID
PubChem CID
Cayman ID
PDB ID

Calculated Physicochemical Properties

Heavy Atoms 21
Rings 4
Aromatic Rings 0
Rotatable Bonds 0
Van der Waals Molecular Volume 302.76
Topological Polar Surface Area 37.30
Hydrogen Bond Donors 1
Hydrogen Bond Acceptors 2
logP 4.25
Molar Refractivity 83.25

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Created at
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Updated at
8th Mar 2023