Structure Database (LMSD)

Common Name
Etiocholanedione
Systematic Name
5β-androstane-3,17-dione
Synonyms
  • Etiocholane-3,17-dione
LM ID
LMST02020058
Formula
C19H28O2
Exact Mass
Calculate m/z
288.20893
Sum Composition
ST 19:2;O2
Status
Curated
Show lipids differing only in stereochemistry/bond geometry
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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

Etiocholanedione is a neurosteroid.1 It inhibits glycine-induced chloride currents (IGly) in isolated rat hippocampal pyramidal neurons when used at a concentration of 50 µM. Etiocholanedione (0.1, 0.3, and 0.5 mM) also inhibits glucose exchange transport in isolated human erythrocytes.2

This information has been provided by Cayman Chemical

References

1. Bukanova, J.V., SoIntserva, I., and Kudova, E. Neurosteroids as selective inhibitors of glycine receptor activity: Structure-activity relationship study on endogenous androstanes and androstenes. Front. Mol. Neurosci. 13, 44 (2020).
2. Lacko, L., Wittke, B., and Geck, P. Interaction of steroids with the transport system of glucose in human erythrocytes. J. Cell. Physiol. 86 Suppl 2(3 Pt 2), 673-680 (1975).

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Homo sapiens (#9606)
Mammalia (#40674)
Metabolism of testosterone in previable human fetuses.,
J Clin Endocrinol Metab, 1975
Pubmed ID: 1133155

String Representations

InChiKey (Click to copy)
RAJWOBJTTGJROA-QJISAEMRSA-N
InChi (Click to copy)
InChI=1S/C19H28O2/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/h12,14-16H,3-11H2,1-2H3/t12-,14+,15+,16+,18+,19+/m1/s1
SMILES (Click to copy)
[C@@]12([H])CC[C@]3([H])CC(CC[C@]3(C)[C@@]1([H])CC[C@]1(C)C(CC[C@@]21[H])=O)=O

Other Databases

Wikipedia
Etiocholanedione
KEGG ID
C03772
HMDB ID
HMDB0003769
CHEBI ID
16985
PubChem CID
440114
SwissLipids ID
SLM:000485681
Cayman ID
34358
PDB ID
ANO

Calculated Physicochemical Properties

Heavy Atoms 21
Rings 4
Aromatic Rings 0
Rotatable Bonds 0
Van der Waals Molecular Volume 300.12
Topological Polar Surface Area 34.14
Hydrogen Bond Donors 0
Hydrogen Bond Acceptors 2
logP 4.17
Molar Refractivity 81.74

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Created at
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Updated at
17th Apr 2025