atovaquone

CHEBI:575568 ·resolve ·ANTIFUNGAL ·EXACT SEEDED

A naphthoquinone compound having a 4-(4-chlorophenyl)cyclohexyl group at the 2-position and a hydroxy substituent at the 3-position. — ChEBI

Machine-generated and unreviewed. Identity, structure and cross-references come straight from ChEBI's and CARD's own data; no curator has signed off on this record yet.

Classification

napthoquinone antibioticsARO:3009154

Strictly broader compounds or drug classes this molecule belongs to.

CHEBI:132157 CHEBI:132157
CHEBI:83403 CHEBI:83403
ARO:3009154 ARO:3009154

Chemical structure

Computed structure properties
Molecular formula	C22H19ClO3
Charge	0
Average mass	366.844 Da
Monoisotopic mass	366.10227 Da
Source	ChEBI
InChIKey	KUCQYCKVKVOKAY-CTYIDZIISA-N

SMILES

O=C1C(O)=C([C@H]2CC[C@H](c3ccc(Cl)cc3)CC2)C(=O)c2ccccc21

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/h1-4,9-13,15,26H,5-8H2/t13-,15-

Also called

2-[trans-4-(4-chlorophenyl)cyclohexyl]-3-hydroxy-1,4-naphthoquinone (EXACT_SYNONYM)— chebi
2-(trans-4-(p-Chlorophenyl)cyclohexyl)-3-hydroxy-1,4-naphthoquinone (EXACT_SYNONYM)— chebi
Acuvel (EXACT_SYNONYM)— chebi
Mepron (EXACT_SYNONYM)— chebi
Wellvone (EXACT_SYNONYM)— chebi

Cross-references

Equivalent identifiers for this same structure in other resources.

ARO:3009155
beilstein:8076827
cas:95233-18-4
drugbank:DB01117
drugcentral:258
kegg.drug:D00236
patent:EP123238
patent:US5053432
wikipedia.en:Atovaquone
chembl:CHEMBL1450
pubchem.compound:74989

Activity roles

Every antimicrobial role a source asserts for this compound — the unreduced evidence behind its antimicrobial_class.

CHEBI:35718 CHEBI:35718
CHEBI:38068 CHEBI:38068

Source concepts

Every upstream concept that resolved to this record. The merge is the product: this is what shows ChEBI and CARD are describing the same structure.

Upstream concepts merged into this record
Source	Native ID	Label	Minted CURIE	Version
ARO	`ARO:3009155`	atovaquone	`antibioticmech:aro-dd10acd6e7`	2026-08-30
CHEBI	`CHEBI:575568`	atovaquone	`antibioticmech:chebi-4288d03c34`	2026-08-30

Mechanism summary

Clinical status: APPROVED

Resistance mechanisms

1 known routes by which microbes resist this compound, grounded in ARO where CARD models them. Grouped by mechanism type — expand a group to see its determinants.

ANTIBIOTIC_TARGET_ALTERATION 1

ANTIBIOTIC_TARGET_ALTERATION
Determinant	ARO ID	Organism	Gene families	Evidence
Pneumocystis jerovecii dhfr with mutations associated with resistance to Trimethoprim sulfamethoxazole combined with Pyrimethamine atovaquone	ARO:3009290	not organism-specific	—	ARO:3009290 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3009155 (atovaquone); database assertion, not a primary citation.)

Curation history

SEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Seeded from data/raw/ inventories (ARO, CHEBI)
RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-08-31 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-08-31 · seed_from_sources
Re-seeded from updated data/raw/ inventories

Provenance

Seeded by scripts/seed_from_sources.py from the committed inventories in data/raw/. View the record.