Structure Database (LMSD)

Common Name
Etiocholanolone
Systematic Name
3α-hydroxy-5β-androstan-17-one
Synonyms
  • 5beta-androsterone
LM ID
LMST02020059
Formula
C19H30O2
Exact Mass
Calculate m/z
290.224581
Sum Composition
ST 19:1;O2
Status
Curated
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View NP-MRD ID(NMR) spectrum

Classification

Category
Main Class
Sub Class
Sterol Lipids [ST]
Steroids [ST02]
C19 steroids (androgens) and derivatives [ST0202]

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).
2. Chouinard, S., Yueh, M.-F., Tukey, R.H., et al. Inactivation by UDP-glucuronosyltransferase enzymes: The end of androgen signaling. J. Steroid. Biochem. Mol. Biol. 109(3-5), 247-253 (2008).
3. Li, P., Bracamontes, J., Katona, B.W., et al. Natural and enantiomeric etiocholanolone interact with distinct sites on the rat α1β2γ2L GABAA receptor. Mol. Pharmacol. 71(6), 1582-1590 (2007).
4. Kaminski, R.M., Marini, H., Kim, W.-J., et al. Anticonvulsant activity of androsterone and etiocholanolone. Epilepsia 46(6), 819-827 (2005).
5. Steinetz, B.G., Randolph, C., Werner, R., et al. Pyrogenicity of etiocholanolone and interleukin-1 in new and old world monkeys. Proc. Soc. Exp. Biol. Med. 217(4), 435-438 (1998).

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
Etiocholanolone
KEGG ID
C04373
HMDB ID
HMDB0000490
CHEBI ID
28195
PubChem CID
5880
Cayman ID
34501
PDB ID
AE2

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