atovaquone   Click here for help

GtoPdb Ligand ID: 9695

Synonyms: 566C80 | Mepron® | Wellvone®
Approved drug PDB Ligand Antimalarial Ligand
atovaquone is an approved drug (FDA (1992))
Compound class: Synthetic organic
Comment: Atovaquone is a synthetic hydroxynaphthoquinone with broad-spectrum antiprotozoal activity. It is an antimalarial drug and used in combination with proguanil.
Note that we have drawn the molecule as specified by the INN record and ChEMBL entry listed on this summary page. The structure for PubChem CID 74989 (link in table below) is shown without specified stereochemistry (InChi Key BSJMWHQBCZFXBR-UHFFFAOYSA-N).
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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

atovaquone is commercially available from our sponsors

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 3
Hydrogen bond donors 1
Rotatable bonds 2
Topological polar surface area 54.37
Molecular weight 366.1
XLogP 6.31
No. Lipinski's rules broken 1
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 Clc1ccc(cc1)C1CCC(CC1)C1=C(O)C(=O)c2c(C1=O)cccc2
Isomeric SMILES Clc1ccc(cc1)[C@@H]1CC[C@H](CC1)C1=C(O)C(=O)c2c(C1=O)cccc2
InChI InChI=1S/C22H19ClO3/c23-16-11-9-14(10-12-16)13-5-7-15(8-6-13)19-20(24)17-3-1-2-4-18(17)21(25)22(19)26/h1-4,9-13,15,26H,5-8H2/t13-,15-
InChI Key KUCQYCKVKVOKAY-CTYIDZIISA-N
Classification Click here for help
Compound class Synthetic organic
Ligand families/groups Antimalarial ligands
Approved drug? Yes (FDA (1992))
IUPAC Name Click here for help
trans-2-[4-(4-Chlorophenyl)cyclohexyl]-3-hydroxy-1,4-naphthalenedione
International Nonproprietary Names Click here for help
INN number INN
6914 atovaquone
Synonyms Click here for help
566C80 | Mepron® | Wellvone®
Database Links Click here for help
CAS Registry No. 95233-18-4 (source: Scifinder)
ChEBI CHEBI:575568
ChEMBL Ligand CHEMBL1450
DrugBank Ligand DB01117
DrugCentral Ligand 258
GtoPdb PubChem SID 348353654
PubChem CID 74989
RCSB PDB Ligand AOQ
Search Google for chemical match using the InChIKey KUCQYCKVKVOKAY-CTYIDZIISA-N
Search Google for chemicals with the same backbone KUCQYCKVKVOKAY
Search PubMed clinical trials atovaquone
Search PubMed titles atovaquone
Search PubMed titles/abstracts atovaquone
UniChem Compound Search for chemical match using the InChIKey KUCQYCKVKVOKAY-CTYIDZIISA-N
UniChem Connectivity Search for chemical match using the InChIKey KUCQYCKVKVOKAY-CTYIDZIISA-N
Wikipedia Atovaquone

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Tocris
Atovaquone (links to external site)
Cat. No. 6358