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.

Label unavailable CHEBI:132157
Label unavailable CHEBI:83403
napthoquinone antibiotics 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

Identifiers for this same structure in other resources. An accession that lands on two different structures in this corpus is withheld from both rather than shown here, since it names at most one of them.

Drug registries

Identifiers that name a drug rather than a structure. One of these can cover a parent compound, its salts and its stereoisomers, which this corpus keeps as separate records, so it is not an equivalence of structure.

Patents and articles

Documents about this compound. A patent covers a class and an article covers a topic; neither identifies a structure.

Activity roles

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

antifungal agent CHEBI:35718
antimalarial 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 source-backed resistance determinants or associations, with ARO grounding where reported. Grouped by reported mechanism type.

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
RESEEDED_FROM_SOURCES 2026-09-10 · 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 (YAML).

Explore across X-Mech: MediaIngredientMech (atovaquone) · CultureMech · NaturalProductMech · PathwayMech · TraitMech