spironolactone   Click here for help

GtoPdb Ligand ID: 2875

Synonyms: Aldactone® | spiractin | spirotone
Approved drug PDB Ligand
spironolactone is an approved drug (FDA (1960))
Compound class: Synthetic organic
Comment: Spironolactone is an orally active, potassium-sparing diuretic, which works by antagonising the effects of aldosterone at renal mineralocorticoid receptors.
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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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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 4
Hydrogen bond donors 0
Rotatable bonds 2
Topological polar surface area 85.74
Molecular weight 416.2
XLogP 3.44
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 CC(=O)SC1CC2=CC(=O)CCC2(C2C1C1CCC3(C1(CC2)C)CCC(=O)O3)C
Isomeric SMILES CC(=O)S[C@@H]1CC2=CC(=O)CC[C@@]2([C@@H]2[C@@H]1[C@@H]1CC[C@]3([C@]1(CC2)C)CCC(=O)O3)C
InChI InChI=1S/C24H32O4S/c1-14(25)29-19-13-15-12-16(26)4-8-22(15,2)17-5-9-23(3)18(21(17)19)6-10-24(23)11-7-20(27)28-24/h12,17-19,21H,4-11,13H2,1-3H3/t17-,18-,19+,21+,22-,23-,24+/m0/s1
InChI Key LXMSZDCAJNLERA-ZHYRCANASA-N
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (1960))
WHO Essential Medicine WHO Essential Medicines List (EML) (23rd List, 2023). Access PDF version.
Click to view more information about the WHO Model Lists of Essential Medicines.
IUPAC Name Click here for help
S-[(7R,8R,9S,10R,13S,14S,17R)-10,13-dimethyl-3,5'-dioxospiro[2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene-17,2'-oxolane]-7-yl] ethanethioate
International Nonproprietary Names Click here for help
INN number INN
987 spironolactone
Synonyms Click here for help
Aldactone® | spiractin | spirotone
Database Links Click here for help
BindingDB Ligand 50228080
CAS Registry No. 52-01-7 (source: Scifinder)
ChEMBL Ligand CHEMBL1393
DrugBank Ligand DB00421
DrugCentral Ligand 2475
GtoPdb PubChem SID 135651065
PubChem CID 5833
RCSB PDB Ligand SNL
Search Google for chemical match using the InChIKey LXMSZDCAJNLERA-ZHYRCANASA-N
Search Google for chemicals with the same backbone LXMSZDCAJNLERA
Search PubMed clinical trials spironolactone
Search PubMed titles spironolactone
Search PubMed titles/abstracts spironolactone
SynPHARM 78981 (in complex with Mineralocorticoid receptor)
UniChem Compound Search for chemical match using the InChIKey LXMSZDCAJNLERA-ZHYRCANASA-N
UniChem Connectivity Search for chemical match using the InChIKey LXMSZDCAJNLERA-ZHYRCANASA-N
Wikipedia Spironolactone

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Tocris
Spironolactone (links to external site)
Cat. No. 2968