Structure Database (LMSD)

Common Name
nandrolone
Systematic Name
17β-hydroxyestr-4-en-3-one
Synonyms
  • (17beta)-17-hydroxyestr-4-en-3-one
  • 17beta-hydroxy-19-nor-4-androsten-3-one
  • 17beta-hydroxy-4-estren-3-one
  • 19-Norandrostenolone
  • 19-Nortestosterone
  • 4-estren-17beta-ol-3-one
  • Nandrolone
LM ID
LMST02010044
Formula
C18H26O2
Exact Mass
Calculate m/z
274.19328
Sum Composition
ST 18:2;O2
Status
Curated
Show lipids differing only in stereochemistry/bond geometry
View MassBank spectra
View NP-MRD ID(NMR) spectrum

Classification

Category
Main Class
Sub Class
Sterol Lipids [ST]
Steroids [ST02]
C18 steroids (estrogens) and derivatives [ST0201]

Biological Context

Nandrolone is an analytical reference standard that is structurally categorized as a steroid. It is a synthetic anabolic androgenic steroid derived from testosterone . Anabolic androgenic steroids have potential therapeutic applications but are considered drugs of abuse.1,2 This product is intended for research and forensic applications.

This information has been provided by Cayman Chemical

References

1. Lood, Y., Eklund, A., Garle, M., et al. Anabolic androgenic steroids in police cases in Sweden 1999-2009. Forensic Sci. Int. 219(1-3), 199-204 (2012).
2. Pan, M.M., and Kovac, J.R. Beyond testosterone cypionate: evidence behind the use of nandrolone in male health and wellness. Transl. Androl. Urol. 5(2), 213-219 (2016).

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
synthetic construct (#32630)
Hydroaromatic steroid hormones. Part I. 10-Nortestosterone,
J Chem S, 1950
Equus caballus (#9796)
Mammalia (#40674)
Steroids in equine testes: the identification of endogenous 19-hydroxy and 19-nor neutral steroids by gas chromatography--mass spectrometry.,
J Endocrinol, 1989
Pubmed ID: 2926297

String Representations

InChiKey (Click to copy)
NPAGDVCDWIYMMC-IZPLOLCNSA-N
InChi (Click to copy)
InChI=1S/C18H26O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h10,13-17,20H,2-9H2,1H3/t13-,14+,15+,16-,17-,18-/m0/s1
SMILES (Click to copy)
C1[C@@]2([H])C(CC[C@]3([H])[C@]2([H])CC[C@@]2([C@H](CC[C@@]32[H])O)C)=CC(=O)C1

Other Databases

Wikipedia
nandrolone
KEGG ID
C07254
HMDB ID
HMDB0002725
CHEBI ID
7466
PubChem CID
9904
SwissLipids ID
SLM:000501177
Cayman ID
21173
PDB ID
6VW
GuidePharm ID
6949

Calculated Physicochemical Properties

Heavy Atoms 20
Rings 4
Aromatic Rings 0
Rotatable Bonds 0
Van der Waals Molecular Volume 282.82
Topological Polar Surface Area 37.30
Hydrogen Bond Donors 1
Hydrogen Bond Acceptors 2
logP 3.78
Molar Refractivity 78.61

Admin

Created at
-
Updated at
-