Basic information
- CAS
137732-39-9- Standard SMILES
O=C1C(=O)c2ccccc2C(O)=C1C1CCC(c2ccc(Cl)cc2)CC1- InChIKey
BSJMWHQBCZFXBR-UHFFFAOYSA-N- Molecular formula
- C22H19ClO3
- Average molar mass
- 366.8 g/mol
- Monoisotopic mass
- 366.10227215
Overview
Atovaquone is a naphthoquinone compound having a 4-(4-chlorophenyl)cyclohexyl group at the 2-position and a hydroxy substituent at the 3-position. It has a role as an antifungal agent, an antimalarial, an EC 1.6.5.3 [NADH:ubiquinone reductase (H(+)-translocating)] inhibitor, an EC 1.3.5.2 [dihydroorotate dehydrogenase (quinone)] inhibitor and an EC 1.10.2.2 (quinol--cytochrome-c reductase) inhibitor. It is a hydroxy-1,4-naphthoquinone and a member of monochlorobenzenes.
Names & identifiers
- Preferred name
- 3-(4-(4-Chlorophenyl)cyclohexyl)-4-hydroxynaphthalene-1,2-dione
- IUPAC
- 3-[4-(4-chlorophenyl)cyclohexyl]-4-hydroxynaphthalene-1,2-dione
- English name
- cis-Atovaquone
- Molecular formula
- C22H19ClO3
- Molecular weight
- 366.84
Names & synonyms
Show more names
Database identifiers
- CAS
137732-39-9、94015-53-9、95233-18-4- PubChem CID
- 74989
- DTXSID
DTXSID20916694- ChEMBL
CHEMBL471792、CHEMBL519462- ChEBI
CHEBI:575568- UNII
- F1W7QUV0KI、Y883P1Z2LT
- EC Number
- 689-795-9
- Nikkaji
- J1.549.967B、J389.528I
Properties
Computed structural properties
- XLogP
- 5.2
- Topological polar surface area
- 54.4 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 2
- Heavy atoms
- 26
- Formal charge
- 0
- Complexity
- 595
Experimental & physicochemical properties
Drugs
Pharmaceuticals
Pharmaceuticals -> Used in Switzerland
Pharmaceuticals -> Listed in ZINC15
Physicochemical properties
- Melting point
- 40 °C · >40°C (dec.)
- Boiling point
- 535 · 535.0±50.0 °C(Predicted)
- Density
- 1.349 · 1.349±0.06 g/cm3(Predicted)
- storage temp.
- Room Temperature, under inert atmosphere
- solubility
- Chloroform (Slightly), Dichloromethane (Slightly, Acetonitrile)
- pka
- 5.01 · 5.01±0.10(Predicted)
- form
- Solid
- color
- Pale Yellow to Light Yellow
- Major Application
- pharmaceutical (small molecule)
- FDA UNII
- 1 W7QUV0KI · F1W7QUV0KI
- UNSPSC Code
- 41116107 · 41116107
- NACRES
- 24 · NA.24
- WGK Germany
- 3 · 3
- Storage Class
- 11 · 11 - Combustible Solids
Safety & regulation
GHS classification
GHS Classification
Warning
H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.
Hazard information
Safety data
- wgk
- 3
- Storage Class
- 11 - Combustible Solids
Chemistry & industry
Pharmacology
Applications
Usescis-Atovaquone is the cis-isomer of Atovaquone (A793500), a hydroxynaphthoquinone derivative that inhibits mitochondrial electron transport.
Suppliers33 total
Additional notes
DefinitionChEBI: Atovaquone is a naphthoquinone compound having a 4-(4-chlorophenyl)cyclohexyl group at the 2-position and a hydroxy substituent at the 3-position. It has a role as an antimalarial, an antifungal agent, an EC 1.3.5.2 [dihydroorotate dehydrogenase (quinone)] inhibitor, an EC 1.6.5.3 [NADH:ubiquinone reductase (H(+)-translocating)] inhibitor and an EC 1.10.2.2 (quinol--cytochrome-c reductase) inhibitor. It is a member of monochlorobenzenes and a hydroxy-1,4-naphthoquinone.
Related reactions
No reaction records under the current filter.
Compound notes
Loading…