Human Metabolome Database Version 3.5

Showing metabocard for Atovaquone (HMDB15249)

Record Information
Version 3.5
Creation Date 2012-09-06 09:16:51 -0600
Update Date 2013-02-08 17:33:17 -0700
HMDB ID HMDB15249
Secondary Accession Numbers None
Metabolite Identification
Common Name Atovaquone
Description Atovaquone is only found in individuals that have used or taken this drug. It is a hydroxynaphthoquinone that has antimicrobial activity and is being used in antimalarial protocols. [PubChem]Atovaquone is a hydroxy- 1, 4- naphthoquinone, an analog of ubiquinone, with antipneumocystis activity. The mechanism of action against Pneumocystis carinii has not been fully elucidated. In Plasmodium species, the site of action appears to be the cytochrome bc1 complex (Complex III). Several metabolic enzymes are linked to the mitochondrial electron transport chain via ubiquinone. Inhibition of electron transport by atovaquone will result in indirect inhibition of these enzymes. The ultimate metabolic effects of such blockade may include inhibition of nucleic acid and ATP synthesis. Atovaquone also has been shown to have good in vitro activity against Toxoplasma gondii.
Structure Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms Not Available
Chemical Formula C22H19ClO3
Average Molecular Weight 366.837
Monoisotopic Molecular Weight 366.102272181
IUPAC Name 2-hydroxy-3-[(1r,4r)-4-(4-chlorophenyl)cyclohexyl]-1,4-dihydronaphthalene-1,4-dione
Traditional IUPAC Name atovaquone
CAS Registry Number 95233-18-4
SMILES OC1=C([C@H]2CC[C@@H](CC2)C2=CC=C(Cl)C=C2)C(=O)C2=CC=CC=C2C1=O
InChI Identifier 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
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aromatic Homomonocyclic Compounds
Class Acenes
Sub Class Naphthalenes
Other Descriptors
  • Aromatic Homomonocyclic Compounds
  • Aromatic Homopolycyclic Compounds
  • naphthoquinone(ChEBI)
  • organochlorine compound(ChEBI)
Substituents
  • Aryl Chloride
  • Benzoquinone
  • Chlorobenzene
  • Cyclohexane
  • Enol
  • Ketone
  • Organochloride
Direct Parent Naphthoquinones
Ontology
Status Expected and Not Quantified
Origin
  • Drug
Biofunction
  • Anti-Infective Agents
  • Antifungal Agents
  • Antimalarials
  • Antiprotozoal Agents
  • Enzyme Inhibitors
Application
  • Pharmaceutical
Cellular locations
  • Cytoplasm
  • Membrane
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility 7.96e-04 g/L Not Available
LogP 5.8 Not Available
Predicted Properties
Property Value Source
Water Solubility 7.960E-04 g/L ALOGPS
LogP 4.74 ALOGPS
LogP 5 ChemAxon
LogS -5.66 ALOGPS
pKa (strongest acidic) 8.23 ChemAxon
pKa (strongest basic) -4.1 ChemAxon
Hydrogen Acceptor Count 3 ChemAxon
Hydrogen Donor Count 1 ChemAxon
Polar Surface Area 54.37 A2 ChemAxon
Rotatable Bond Count 2 ChemAxon
Refractivity 103.11 ChemAxon
Polarizability 39.55 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Expected but not Quantified
Not Applicable Not Available Not Available Taking drug identified by DrugBank entry DB01117
  • Not Applicable
Urine Expected but not Quantified
Not Applicable Not Available Not Available Taking drug identified by DrugBank entry DB01117
  • Not Applicable
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID DB01117 Link_out
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID Not Available
KNApSAcK ID Not Available
Chemspider ID 10482034 Link_out
KEGG Compound ID C06835 Link_out
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Atovaquone Link_out
NuGOwiki Link HMDB15249 Link_out
Metagene Link HMDB15249 Link_out
METLIN ID Not Available
PubChem Compound Not Available
PDB ID Not Available
ChEBI ID 575568 Link_out
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Not Available
General References Not Available

Enzymes
Name: Dihydroorotate dehydrogenase (quinone), mitochondrial
Reactions: Not Available
Gene Name: DHODH
Uniprot ID: Q02127 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 2C9
Reactions: Not Available
Gene Name: CYP2C9
Uniprot ID: P11712 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA