Atovaquone
Athanor · official
C22H19ClO3 · 366.8 g/mol
IUPAC name: 3-[4-(4-chlorophenyl)cyclohexyl]-4-hydroxynaphthalene-1,2-dione
Also called Mepron, Malarone, antiparasitic
WarningCauses skin irritation · Causes serious eye irritation · May cause respiratory irritationNames and identifiers
- IUPAC name
- 3-[4-(4-chlorophenyl)cyclohexyl]-4-hydroxynaphthalene-1,2-dione
- Synonyms
- Mepron, Malarone, antiparasitic
+ 35 more
3-[4-(4-chlorophenyl)cyclohexyl]-4-hydroxynaphthalene-1,2-dione, DTXSID20916694, 3-(4-(4-chlorophenyl)cyclohexyl)-4-hydroxynaphthalene-1,2-dione, RefChem:1066764, DTXCID20888847, 630-425-2, Wellvone, Acuvel, cis-Atovaquone, 566C80, Atavaquone, Mepron (antipneumocystic), CIS-ATOVAQUONE (RACEMIC), Atovaquone EP Impurity B, 2-(TRANS-4-(4-CHLOROPHENYL)CYCLOHEXYL)-3-HYDROXY-1,4-NAPHTHALENEDIONE, BW 566C, 566C, C22H19ClO3, atovacuona, Atovaquona, 2-(trans-4-(p-Chlorophenyl)cyclohexyl)-3-hydroxy-1,4-naphthoquinone, ATOVAQUONE-D4, DTXSID7022629, 2-[trans-4-(4-chlorophenyl)cyclohexyl]-3-hydroxy-1,4-naphthoquinone, 2-((1r,4r)-4-(4-chlorophenyl)cyclohexyl)-3-hydroxynaphthalene-1,4-dione, ATOVAQUONE [MI], SpecPlus_000686, ATOVAQUONE [USAN], MFCD00889188, F1W7QUV0KI, NSC-759582, 2-(4-(4-Chlorophenyl)cyclohexyl)-3-hydroxynaphthalene-1,4-dione, 2-[4-(4-chlorophenyl)cyclohexyl]-3-hydroxy-1,4-dihydronaphthalene-1,4-dione, Y883P1Z2LT, 2-(4-(4-Chlorophenyl)cyclohexyl)-3-hydroxy-1,4-naphthoquinone
- Molecular formula
- C22H19ClO3
- Empirical formula
- C22H19ClO3
- Molecular weight
- 366.8 g/mol
- Exact mass
- 366.10227
- CAS number
- 95233-18-4
- PubChem CID
- 74989
- Canonical SMILES
- C1CC(CCC1C2=CC=C(C=C2)Cl)C3=C(C4=CC=CC=C4C(=O)C3=O)O
- Isomeric SMILES
- C1CC(CCC1C2=CC=C(C=C2)Cl)C3=C(C4=CC=CC=C4C(=O)C3=O)O
- InChI
- 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/h1-4,9-13,15,24H,5-8H2
- InChIKey
- BSJMWHQBCZFXBR-UHFFFAOYSA-N
- Molfile
Names, InChI and the identifiers from PubChem, retrieved 2026-10-14.
Calculated
- Heavy atoms
- 26
- Rings
- 4
- Aromatic rings
- 2
- Fraction sp³ carbons (Fsp3)
- 0.27
- H-bond donors
- 1
- H-bond acceptors
- 3
- Rotatable bonds
- 2
- TPSA (Ų)
- 54.4
- Formal charge
- 0
- XLogP3
- 5.2 PubChem
- Complexity
- 595 PubChem
- Stereocenters
- 0 defined, 2 undefinedCIP: C14: undefined · C17: undefined
- Double-bond geometry
- None specified
- Point group
- C1 of one 3D conformer with its hydrogens, by Athanor’s engine (as in the app)
Elemental analysis
- C72.03%
- H5.22%
- Cl9.66%
- O13.08%
Isotope pattern
Each peak is a nominal mass with its abundance-weighted exact mass, as a percentage of the tallest, from IUPAC natural isotope abundances.
Computed from the structure with RDKit 2026.09 when this page was built, beside PubChem's own computed values from its record; where the two differ, both are shown.
Predicted
- log P
- 5.51 Crippen (Wildman and Crippen 1999)
- log S (water solubility)
- -5.79 ESOL (Delaney 2004), log mol/L
- Synthetic accessibility
- 2.29 SA score, 1 easy to 10 hard (Ertl and Schuffenhauer 2009)
Drug-likeness: Lipinski’s rule of five
- Molecular weight ≤ 500: 366.84
- log P ≤ 5 (Crippen): 5.51
- H-bond donors ≤ 5: 1
- H-bond acceptors ≤ 10: 3
Breaks 1 of the four rules.
¹³C NMR shifts, predicted
Predictions, not measurements; each names its method. A measured log P, where a source reports one, is under Physical properties.
Safety
Warning
From European Chemicals Agency (ECHA). Source [1].
- Harmful or irritant
- H315Causes skin irritation
- H319Causes serious eye irritation
- H335May cause respiratory irritation
Precautionary statements: P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, P501
Safety data sheets on the supplier’s page: 10X CHEM, 001Chemical, LGC Standards.
Always read the supplier’s safety data sheet before working with it.
Spectra
- GC-MSNIST Mass Spectrometry Data Center · NIST Mass Spectrometry Data Center
- MS-MSNIST Mass Spectrometry Data Center (IT/ion trap)
- LC-MSMassBank Europe (Exploris 480 Orbitrap (Thermo Scientific) · LC-ESI-QFT · NEGATIVE) · MassBank of North America (MoNA) (qTof · positive)
Experimental spectra held by these sources; each link opens the source's own record.
Literature
Reading PubChem, OpenAlex and GSRS…
Bioactivity
Reading ChEMBL…
References
- [1]European Chemicals Agency (ECHA) · ECHA legal notice: reuse with acknowledgement · via PubChem · retrieved 2026-10-14
- [2]NIST Mass Spectrometry Data Center · Linked only · via PubChem · retrieved 2026-10-14
- [3]MassBank Europe · Linked only · via PubChem · retrieved 2026-10-14
- [4]MassBank of North America (MoNA) · CC BY 4.0 · via PubChem · retrieved 2026-10-14
- ·Calculated values: computed by Athanor with RDKit 2026.09 from the structure.
- ·Literature on PubChem
Data last updated 2026-10-14.