atovaquone   

GtoPdb Ligand ID: 9695

Synonyms: 566C80 | Mepron® | Wellvone®
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).
2D Structure
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Physico-chemical Properties
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
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
Compound class Synthetic organic
Ligand families/groups Antimalarial ligands
Approved drug? Yes (FDA (1992))
IUPAC Name
trans-2-[4-(4-Chlorophenyl)cyclohexyl]-3-hydroxy-1,4-naphthalenedione
International Nonproprietary Names
INN number INN
6914 atovaquone
Synonyms
566C80 | Mepron® | Wellvone®
Database Links
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
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Search UniChem for chemical match using the InChIKey KUCQYCKVKVOKAY-CTYIDZIISA-N
Search UniChem for chemicals with the same backbone KUCQYCKVKVOKAY
Wikipedia Atovaquone

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Atovaquone
Cat. No. 6358