AOQ

2-[trans-4-(4-chlorophenyl)cyclohexyl]-3-hydroxynaphthalene-1,4-dione

Created: 2014-06-03
Last modified:  2021-03-01

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Chemical Details

Formal Charge0
Atom Count45
Chiral Atom Count0
Bond Count48
Aromatic Bond Count12
2D diagram of AOQ
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Chemical Component Summary

Name2-[trans-4-(4-chlorophenyl)cyclohexyl]-3-hydroxynaphthalene-1,4-dione
SynonymsAtovaquone
Systematic Name (OpenEye OEToolkits)2-[4-(4-chlorophenyl)cyclohexyl]-3-oxidanyl-naphthalene-1,4-dione
FormulaC22 H19 Cl O3
Molecular Weight366.837
TypeNON-POLYMER

Chemical Descriptors

TypeProgram Version Descriptor
SMILESACDLabs12.01Clc1ccc(cc1)C4CCC(C=3C(=O)c2ccccc2C(=O)C=3O)CC4
SMILESCACTVS3.385OC1=C([CH]2CC[CH](CC2)c3ccc(Cl)cc3)C(=O)c4ccccc4C1=O
SMILESOpenEye OEToolkits1.9.2c1ccc2c(c1)C(=O)C(=C(C2=O)O)C3CCC(CC3)c4ccc(cc4)Cl
Canonical SMILESCACTVS3.385 OC1=C([C@H]2CC[C@@H](CC2)c3ccc(Cl)cc3)C(=O)c4ccccc4C1=O
Canonical SMILESOpenEye OEToolkits1.9.2 c1ccc2c(c1)C(=O)C(=C(C2=O)O)C3CCC(CC3)c4ccc(cc4)Cl
InChIInChI1.03 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-
InChIKeyInChI1.03 KUCQYCKVKVOKAY-CTYIDZIISA-N

Drug Info: DrugBank

DrugBank IDDB01117 
NameAtovaquone
Groups approved
DescriptionAtovaquone is a hydroxynaphthoquinone, or an analog of ubiquinone, that has antimicrobial and antipneumocystis activity. It is being used in antimalarial protocols.
Synonyms
  • 2-(trans-4-(p-Chlorophenyl)cyclohexyl)-3-hydroxy-1,4-naphthoquinone
  • Atovacuona
  • Atovaquone
Brand Names
  • Mepron Tab 250mg
  • Apo-atovaquone
  • Mepron
  • Malarone
  • Atovaquone and Proguanil Hydrochloride
IndicationFor the treatment or prevention of <i>Pneumocystis carinii</i> pneumonia in patients who are intolerant to trimethoprim-sulfamethoxazole (TMP-SMX). Also indicated for the acute oral treatment of mild to moderate PCP in patients who are intolerant to TMP-SMX.
Categories
  • Anti-Infective Agents
  • Antibiotics for Pneumocystis Pneumonia
  • Antimalarials
  • Antiparasitic Agents
  • Antiparasitic Products, Insecticides and Repellents
ATC-Code
  • P01AX06
  • P01BB51
CAS number95233-18-4

Drug Targets

NameTarget SequencePharmacological ActionActions
Cytochrome bMNFYSINLVKAHLINYPCPLNINFLWNYGFLLGIIFFIQIITGVFLASRY...unknowninhibitor
Dihydroorotate dehydrogenase (quinone), mitochondrialMISKLKPQFMFLPKKHILSYCRKDVLNLFEQKFYYTSKRKESNNMKNESL...unknowninhibitor
Dihydroorotate dehydrogenase (quinone), mitochondrialMAWRHLKKRAQDAVIILGGGGLLFASYLMATGDERFYAEHLMPTLQGLLD...unknowninhibitor
Cytochrome P450 2C9MDSLVVLVLCLSCLLLLSLWRQSSGRGKLPPGPTPLPVIGNILQIGIKDI...unknowninhibitor
Cytochrome P450 3A4MALIPDLAMETWLLLAVSLVLLYLYGTHSHGLFKKLGIPGPTPLPFLGNI...unknownsubstrate
View More
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
CCDC/CSD UMOMAL, WEXLOC, UMOMAL02, UMOMAL01, UMOMAL03, UMOMAL04
COD 7210170, 7210169, 7210168