CHEBI:575568 - atovaquone

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ChEBI Name atovaquone
ChEBI ID CHEBI:575568
Definition A naphthoquinone compound having a 4-(4-chlorophenyl)cyclohexyl group at the 2-position and a hydroxy substituent at the 3-position.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:2912
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Formula C22H19ClO3
Net Charge 0
Average Mass 366.83700
Monoisotopic Mass 366.102
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-
InChIKey KUCQYCKVKVOKAY-CTYIDZIISA-N
SMILES OC1=C([C@H]2CC[C@@H](CC2)c2ccc(Cl)cc2)C(=O)c2ccccc2C1=O
Roles Classification
Biological Role(s): EC 1.3.5.2 [dihydroorotate dehydrogenase (quinone)] inhibitor
An EC 1.3.5.* (oxidoreductase acting on CH-CH of donor with a quinone or related compound as acceptor) inhibitor that interferes with the action of dihydroorotate dehydrogenase (quinone), EC 1.3.5.2.
EC 1.6.5.3 [NADH:ubiquinone reductase (H(+)-translocating)] inhibitor
A respiratory-chain inhibitor that interferes with the action of the the enzyme NADH:ubiquinone reductase (H+-translocating), EC 1.6.5.3.
EC 1.10.2.2 (quinol--cytochrome-c reductase) inhibitor
An EC 1.10.2.* (oxidoreductase acting on diphenols and related substances as donors with a cytochrome as acceptor) inhibitor that interferes with the action of quinolcytochrome-c reductase (EC 1.10.2.2).
antimalarial
A drug used in the treatment of malaria. Antimalarials are usually classified on the basis of their action against Plasmodia at different stages in their life cycle in the human.
antifungal agent
An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
Application(s): antimalarial
A drug used in the treatment of malaria. Antimalarials are usually classified on the basis of their action against Plasmodia at different stages in their life cycle in the human.
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ChEBI Ontology
Outgoing atovaquone (CHEBI:575568) has role antifungal agent (CHEBI:35718)
atovaquone (CHEBI:575568) has role antimalarial (CHEBI:38068)
atovaquone (CHEBI:575568) has role EC 1.10.2.2 (quinol—cytochrome-c reductase) inhibitor (CHEBI:77106)
atovaquone (CHEBI:575568) has role EC 1.3.5.2 [dihydroorotate dehydrogenase (quinone)] inhibitor (CHEBI:77103)
atovaquone (CHEBI:575568) has role EC 1.6.5.3 [NADH:ubiquinone reductase (H+-translocating)] inhibitor (CHEBI:38503)
atovaquone (CHEBI:575568) is a hydroxy-1,4-naphthoquinone (CHEBI:132157)
atovaquone (CHEBI:575568) is a monochlorobenzenes (CHEBI:83403)
IUPAC Name
2-[trans-4-(4-chlorophenyl)cyclohexyl]-3-hydroxy-1,4-naphthoquinone
INN Source
atovaquone KEGG DRUG
Synonyms Sources
2-(trans-4-(p-Chlorophenyl)cyclohexyl)-3-hydroxy-1,4-naphthoquinone ChemIDplus
Acuvel KEGG COMPOUND
Mepron KEGG COMPOUND
Wellvone KEGG COMPOUND
Database Links Databases
258 DrugCentral
Atovaquone Wikipedia
D00236 KEGG DRUG
DB01117 DrugBank
EP123238 Patent
US5053432 Patent
View more database links
Registry Numbers Types Sources
8076827 Beilstein Registry Number Beilstein
95233-18-4 CAS Registry Number KEGG COMPOUND
95233-18-4 CAS Registry Number ChemIDplus
95233-18-4 CAS Registry Number KEGG DRUG
95233-18-4 CAS Registry Number DrugBank
Citations Waiting for Citations Types Sources
10658902 PubMed citation Europe PMC
11956677 PubMed citation Europe PMC
12791689 PubMed citation Europe PMC
14727190 PubMed citation Europe PMC
15044733 PubMed citation Europe PMC
15718226 PubMed citation Europe PMC
21735454 PubMed citation Europe PMC
23292347 PubMed citation Europe PMC
Last Modified
22 February 2017