ContaminantDB: Atovaquone

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-22 03:37:21 UTC

Update Date

2016-11-09 01:15:26 UTC

Accession Number

CHEM016571

Identification

Common Name

Atovaquone

Class

Small Molecule

Description

Atovaquone is a hydroxynaphthoquinone, or an analog of , that has antimicrobial and antipneumocystis activity. It is being used in antimalarial protocols.

Contaminant Sources

HMDB Contaminants - Urine
STOFF IDENT Compounds
ToxCast & Tox21 Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2-(trans-4-(p-Chlorophenyl)cyclohexyl)-3-hydroxy-1,4-naphthoquinone	ChEBI
Acuvel	ChEBI
Mepron	ChEBI
Wellvone	ChEBI

Chemical Formula

C₂₂H₁₉ClO₃

Average Molecular Mass

366.837 g/mol

Monoisotopic Mass

366.102 g/mol

CAS Registry Number

95233-18-4

IUPAC Name

2-hydroxy-3-[(1r,4r)-4-(4-chlorophenyl)cyclohexyl]-1,4-dihydronaphthalene-1,4-dione

Traditional Name

atovaquone

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

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).

Kingdom

Super Class

Class

Sub Class

Direct Parent

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 Framework

Aromatic homopolycyclic compounds

External Descriptors

naphthoquinone (CHEBI:575568 )
monochlorobenzenes (CHEBI:575568 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.0008 g/L	ALOGPS
logP	4.74	ALOGPS
logP	5	ChemAxon
logS	-5.7	ALOGPS
pKa (Strongest Acidic)	8.23	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	54.37 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	103.11 m³·mol⁻¹	ChemAxon
Polarizability	39.55 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0f79-0829000000-4b88673ebb0412947f94	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-0fe0-4923400000-57e2c568b6623d698ca6	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-0udj-0910000000-f7b2a59bcc1e1195bf1f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-066r-0968000000-4d83793ef10d849ce35e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0119000000-5f209ebb20fbf0259351	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-066s-0897000000-79bdad72004b4a42d8c7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0zi0-6931000000-6ac22d2b522d431d04c1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0009000000-d52277af59ec8f79fa22	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-0419000000-87e2b6ffb344b5930d26	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0kor-2913000000-40a03b8ec8ba93c6c3e7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0009000000-8e8c322593e61a1fcd3a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014j-0009000000-887d32008948c60e375f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052u-1927000000-b03db76b9884df28bfe8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0009000000-811d88e8ea937d34fe7b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-0009000000-05e44597e6bf573643ee	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001i-9222000000-b6a748454bc56651ddf0	Spectrum