nandrolone   Click here for help

GtoPdb Ligand ID: 6949

Synonyms: 19-norandrostenolone | Deca-Durabolin® (decanoate ester) | Durabolin® (phenylpropionate ester)
Approved drug PDB Ligand
nandrolone is an approved drug (FDA (1959))
Compound class: Synthetic organic
Comment: An androgen receptor agonist with associated anabolic properties. The INN record for nandrolone is for the core compound without the decanoate side chain, but other national commissions use nandrolone decanoate to name nadrolone. The first US FDA nandrolone based drug approval was for nandrolone phenpropionate in 1959, since then many formulations have been approved but subsequently discontinued. Our record for nandrolone is intended to cover various fomulations of the compound including nandrolone phenpropionate (PubChem CID 229455) and nandrolone decanoate (PubChem CID 9677).
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species

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View more information in the IUPHAR Pharmacology Education Project: nandrolone

2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 2
Hydrogen bond donors 1
Rotatable bonds 0
Topological polar surface area 37.3
Molecular weight 274.19
XLogP 3.22
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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Canonical SMILES O=C1CCC2C(=C1)CCC1C2CCC2(C1CCC2O)C
Isomeric SMILES O=C1CC[C@H]2C(=C1)CC[C@@H]1[C@@H]2CC[C@]2([C@H]1CC[C@@H]2O)C
InChI 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
InChI Key NPAGDVCDWIYMMC-IZPLOLCNSA-N
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (1959))
IUPAC Name Click here for help
(8R,9S,10R,13S,14S,17S)-17-hydroxy-13-methyl-2,6,7,8,9,10,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-one
International Nonproprietary Names Click here for help
INN number INN
295 nandrolone
Synonyms Click here for help
19-norandrostenolone | Deca-Durabolin® (decanoate ester) | Durabolin® (phenylpropionate ester)
Database Links Click here for help
CAS Registry No. 434-22-0
ChEBI CHEBI:7466
ChEMBL Ligand CHEMBL757
DrugBank Ligand DB08804, DB00984
DrugCentral Ligand 1879
GtoPdb PubChem SID 178103531
PubChem CID 9904
RCSB PDB Ligand 6VW
Search Google for chemical match using the InChIKey NPAGDVCDWIYMMC-IZPLOLCNSA-N
Search Google for chemicals with the same backbone NPAGDVCDWIYMMC
Search PubMed clinical trials nandrolone
Search PubMed titles nandrolone
Search PubMed titles/abstracts nandrolone
UniChem Compound Search for chemical match using the InChIKey NPAGDVCDWIYMMC-IZPLOLCNSA-N
UniChem Connectivity Search for chemical match using the InChIKey NPAGDVCDWIYMMC-IZPLOLCNSA-N
Wikipedia Nandrolone