Atovaquone (CED0003668)

Record Information
Version1.0
Creation Date2016-05-22 03:37:21 UTC
Update Date2026-05-14 16:57:58 UTC
SynCED IDCED0003668
Secondary Accession Numbers
  • CHEM016571
Identification
Common NameAtovaquone
ClassSmall Molecule
Description
Atovaquone is an organic compound with the formula C22H19ClO3 and an average molecular weight of 366.84 g/mol. Atovaquone belongs to the naphthoquinones, a subclass of naphthalenes within the organic compounds. It is utilized in healthcare, pharmaceuticals, and veterinary products as an antiprotozoal agent, with oral administration as the recorded route of exposure. The compound acts on three recorded protein targets. It serves as an inhibitor of mitochondrial dihydroorotate dehydrogenase (quinone) (DHODH) and dihydroorotate dehydrogenase (quinone), mitochondrial, as well as cytochrome b (MT-CYB).
Contaminant TypeNot Available
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
2-(trans-4-(p-Chlorophenyl)cyclohexyl)-3-hydroxy-1,4-naphthoquinoneChEBI
AcuvelChEBI
MepronChEBI
WellvoneChEBI
Chemical FormulaC22H19ClO3
Average Molecular Mass366.837 g/mol
Monoisotopic Mass366.102 g/mol
CAS Registry Number95233-18-4
IUPAC Name2-hydroxy-3-[(1r,4r)-4-(4-chlorophenyl)cyclohexyl]-1,4-dihydronaphthalene-1,4-dione
Traditional Nameatovaquone
SMILESOC1=C([C@H]2CC[C@@H](CC2)C2=CC=C(Cl)C=C2)C(=O)C2=CC=CC=C2C1=O
InChI IdentifierInChI=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 KeyKUCQYCKVKVOKAY-CTYIDZIISA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as naphthoquinones. Naphthoquinones are compounds containing a naphthohydroquinone moiety, which consists of a benzene ring linearly fused to a bezene-1,4-dione (quinone).
KingdomOrganic compounds
Super ClassBenzenoids
ClassNaphthalenes
Sub ClassNaphthoquinones
Direct ParentNaphthoquinones
Alternative Parents
Substituents
  • Naphthoquinone
  • Quinone
  • Aryl ketone
  • Chlorobenzene
  • Halobenzene
  • Aryl chloride
  • Monocyclic benzene moiety
  • Aryl halide
  • Vinylogous acid
  • Ketone
  • Enol
  • Organic oxide
  • Organooxygen compound
  • Organochloride
  • Organohalogen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0008 g/LALOGPS
logP4.74ALOGPS
logP5ChemAxon
logS-5.7ALOGPS
pKa (Strongest Acidic)8.23ChemAxon
pKa (Strongest Basic)-4.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area54.37 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity103.11 m³·mol⁻¹ChemAxon
Polarizability39.55 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0f79-0829000000-4b88673ebb0412947f94Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0fe0-4923400000-57e2c568b6623d698ca6Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udj-0910000000-f7b2a59bcc1e1195bf1fNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-066r-0968000000-4d83793ef10d849ce35eNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-0119000000-5f209ebb20fbf0259351Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-066s-0897000000-79bdad72004b4a42d8c7Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0zi0-6931000000-6ac22d2b522d431d04c1Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-0009000000-d52277af59ec8f79fa22Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-0419000000-87e2b6ffb344b5930d26Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0kor-2913000000-40a03b8ec8ba93c6c3e7Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-0009000000-8e8c322593e61a1fcd3aNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014j-0009000000-887d32008948c60e375fNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-052u-1927000000-b03db76b9884df28bfe8Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-0009000000-811d88e8ea937d34fe7bNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-0009000000-05e44597e6bf573643eeNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-9222000000-b6a748454bc56651ddf0Not AvailableView Spectrum
Toxicity Profile
Toxicity Values
Toxicity ValueOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalToxicity RatingReference
2396.0 Log mg/kg [1300:4300]RatLD50oralpredictedNot AvailableNot Available
Toxicity / Toxin ClassNot Available
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Health Effects
Health EffectRelationshipDirectionDescriptionReference
Exposure Sources
Source IDSourceSectorReference
CEDs000385Antiprotozoals?Antiprotozoals are synthetic chemicals designed to target and eliminate protozoan infections in humans and animals.Healthcare, pharmaceuticals & veterinary productsNot Available
Pathways
0 pathwaysPathway Source: PathBank

No pathways found

No metabolic pathways have been associated with this synthetic chemical

Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Dihydroorotate dehydrogenase (quinone), mitochondrial structureClick to view 3D structureDihydroorotate dehydrogenase (quinone), mitochondrialQ02127HumansPredicted (SEA)
Prediction Confidence Score
0.435
Applicability Domain
1.0
Statistical Significance
6.00e-05
Supporting Reference Compounds
33
E-value
0.467095
Dihydroorotate dehydrogenase (quinone), mitochondrial structureClick to view 3D structureDihydroorotate dehydrogenase (quinone), mitochondrialG4VFD7Schistosoma mansoniPredicted (SEA)
Prediction Confidence Score
0.416
Applicability Domain
1.0
Statistical Significance
1.00e-05
Supporting Reference Compounds
5
E-value
0.0778492
Click to view 3D structureChemokine receptorQ9MYJ9Oryctolagus cuniculusPredicted (SEA)
Prediction Confidence Score
0.368
Applicability Domain
0.368
Statistical Significance
3.30e-04
Supporting Reference Compounds
1
E-value
2.56902
Broad substrate specificity ATP-binding cassette transporter ABCG2 structureClick to view 3D structureBroad substrate specificity ATP-binding cassette transporter ABCG2Q9UNQ0HumansPredicted (SEA)
Prediction Confidence Score
0.354
Applicability Domain
1.0
Statistical Significance
0.0074
Supporting Reference Compounds
126
E-value
57.6863
Dihydroorotate dehydrogenase structureClick to view 3D structureDihydroorotate dehydrogenaseQ54A96Plasmodium falciparumPredicted (SEA)
Prediction Confidence Score
0.33
Applicability Domain
1.0
Statistical Significance
3.50e-04
Supporting Reference Compounds
23
E-value
2.72472
Dihydroorotate dehydrogenase (quinone), mitochondrial structureClick to view 3D structureDihydroorotate dehydrogenase (quinone), mitochondrialQ63707Rattus norvegicusPredicted (SEA)
Prediction Confidence Score
0.329
Applicability Domain
1.0
Statistical Significance
3.40e-04
Supporting Reference Compounds
15
E-value
2.64687
Protein RecA structureClick to view 3D structureProtein RecAP9WHJ3Mycobacterium tuberculosisPredicted (SEA)
Prediction Confidence Score
0.321
Applicability Domain
0.347
Statistical Significance
0.0049
Supporting Reference Compounds
296
E-value
38.1461
Click to view 3D structureDihydroorotate dehydrogenase (fumarate)P28272Saccharomyces cerevisiae S288cPredicted (SEA)
Prediction Confidence Score
0.321
Applicability Domain
1.0
Statistical Significance
1.00e-05
Supporting Reference Compounds
12
E-value
0.0778492
Click to view 3D structureHexokinase HKDC1Q2TB90HumansPredicted (SEA)
Prediction Confidence Score
0.301
Applicability Domain
0.327
Statistical Significance
0.0015
Supporting Reference Compounds
69
E-value
11.5995
Apoptotic protease-activating factor 1 structureClick to view 3D structureApoptotic protease-activating factor 1O14727HumansPredicted (SEA)
Prediction Confidence Score
0.289
Applicability Domain
0.315
Statistical Significance
0.0028
Supporting Reference Compounds
112
E-value
21.7978
Click to view 3D structureStreptokinase AP10520Streptococcus pyogenes serotype M1Predicted (SEA)
Prediction Confidence Score
0.286
Applicability Domain
0.315
Statistical Significance
0.0353
Supporting Reference Compounds
425
E-value
274.652
D(2) dopamine receptor structureClick to view 3D structureD(2) dopamine receptorP14416HumansPredicted (SEA)
Prediction Confidence Score
0.283
Applicability Domain
0.31
Statistical Significance
0.1301
Supporting Reference Compounds
1103
E-value
1013.05
Click to view 3D structureTubulin alpha chainQ27352Trypanosoma cruziPredicted (SEA)
Prediction Confidence Score
0.281
Applicability Domain
0.298 Low confidence
Statistical Significance
1.70e-04
Supporting Reference Compounds
2
E-value
1.32344
Protein S100-A4 structureClick to view 3D structureProtein S100-A4P26447HumansPredicted (SEA)
Prediction Confidence Score
0.28
Applicability Domain
0.366
Statistical Significance
5.50e-04
Supporting Reference Compounds
8
E-value
4.28171
Induced myeloid leukemia cell differentiation protein Mcl-1 structureClick to view 3D structureInduced myeloid leukemia cell differentiation protein Mcl-1Q07820HumansPredicted (SEA)
Prediction Confidence Score
0.276
Applicability Domain
0.289 Low confidence
Statistical Significance
0.0407
Supporting Reference Compounds
343
E-value
316.768
Indoleamine 2,3-dioxygenase 1 structureClick to view 3D structureIndoleamine 2,3-dioxygenase 1P14902HumansPredicted (SEA)
Prediction Confidence Score
0.276
Applicability Domain
0.351
Statistical Significance
0.0071
Supporting Reference Compounds
108
E-value
55.6622
D(3) dopamine receptor structureClick to view 3D structureD(3) dopamine receptorP35462HumansPredicted (SEA)
Prediction Confidence Score
0.276
Applicability Domain
0.31
Statistical Significance
0.1249
Supporting Reference Compounds
861
E-value
972.648
Toll-like receptor 9 structureClick to view 3D structureToll-like receptor 9Q9NR96HumansPredicted (SEA)
Prediction Confidence Score
0.274
Applicability Domain
0.315
Statistical Significance
0.0092
Supporting Reference Compounds
111
E-value
71.4656
Amine oxidase [flavin-containing] A structureClick to view 3D structureAmine oxidase [flavin-containing] AP21397HumansPredicted (SEA)
Prediction Confidence Score
0.273
Applicability Domain
0.306
Statistical Significance
0.0428
Supporting Reference Compounds
241
E-value
332.961
G-protein coupled receptor 35 structureClick to view 3D structureG-protein coupled receptor 35Q9HC97HumansPredicted (SEA)
Prediction Confidence Score
0.272
Applicability Domain
0.34
Statistical Significance
0.0105
Supporting Reference Compounds
115
E-value
81.586
5-hydroxytryptamine receptor 2A structureClick to view 3D structure5-hydroxytryptamine receptor 2AP28223HumansPredicted (SEA)
Prediction Confidence Score
0.272
Applicability Domain
0.323
Statistical Significance
0.1618
Supporting Reference Compounds
955
E-value
1259.52
Tyrosyl-DNA phosphodiesterase 2 structureClick to view 3D structureTyrosyl-DNA phosphodiesterase 2O95551HumansPredicted (SEA)
Prediction Confidence Score
0.271
Applicability Domain
0.306
Statistical Significance
0.0021
Supporting Reference Compounds
60
E-value
16.6597
Cysteine protease ATG4B structureClick to view 3D structureCysteine protease ATG4BQ9Y4P1HumansPredicted (SEA)
Prediction Confidence Score
0.269
Applicability Domain
0.306
Statistical Significance
0.0052
Supporting Reference Compounds
80
E-value
40.5594
Isoprenyl transferase structureClick to view 3D structureIsoprenyl transferaseQ97SR4Streptococcus pneumoniae serotype 4 (strain ATCC BAA-334 / TIGR4)Predicted (SEA)
Prediction Confidence Score
0.267
Applicability Domain
0.281 Low confidence
Statistical Significance
0.002
Supporting Reference Compounds
2
E-value
15.492
Serine/threonine-protein kinase pim-1 structureClick to view 3D structureSerine/threonine-protein kinase pim-1P11309HumansPredicted (SEA)
Prediction Confidence Score
0.266
Applicability Domain
0.304
Statistical Significance
0.242
Supporting Reference Compounds
967
E-value
1884.03
Concentrations
Not Available
External Links
DrugBank IDDB01117
HMDB IDHMDB0015249
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkAtovaquone
Chemspider ID10482034
ChEBI ID575568
PubChem Compound IDNot Available
Kegg Compound IDC06835
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available