fenamidone

CHEBI:83258 ·resolve ·ANTIFUNGAL ·EXACT SEEDED

A member of the class of imidazolones that is 3,5-dihydroimidazol-4-one substituted at position 2 by a methylthiogroup, at position 3 by an anilino group and at position 5 by phenyl and methyl groups (the S-enantiomer). A fungicide effective against Oomycete diseases such as downy mildew and certain leaf spot diseases. — 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

Strictly broader compounds or drug classes this molecule belongs to.

Label unavailable CHEBI:16385
Label unavailable CHEBI:20432
Label unavailable CHEBI:35363
imidazole fungicide CHEBI:87068

Chemical structure

Computed structure properties
Molecular formula	C17H17N3OS
Charge	0
Average mass	311.41 Da
Monoisotopic mass	311.10923 Da
Source	ChEBI
InChIKey	LMVPQMGRYSRMIW-KRWDZBQOSA-N

SMILES

CSC1=N[C@@](C)(c2ccccc2)C(=O)N1Nc1ccccc1

InChI

InChI=1S/C17H17N3OS/c1-17(13-9-5-3-6-10-13)15(21)20(16(18-17)22-2)19-14-11-7-4-8-12-14/h3-12,19H,1-2H3/t17-/m0/s1

Also called

(5S)-3-anilino-5-methyl-2-(methylsulfanyl)-5-phenyl-3,5-dihydro-4H-imidazol-4-one (EXACT_SYNONYM)— chebi
(5S)-3,5-dihydro-5-methyl-2-(methylthio)-5-phenyl-3-(phenylamino)-4H-imidazol-4-one (EXACT_SYNONYM)— chebi
(S)-1-anilino-4-methyl-2-methylthio-4-phenylimidazolin-5-one (EXACT_SYNONYM)— chebi
1-Anilino-4-methyl-2-methylthio-4-phenylimidazolin-5-one (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.

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.

quinone outside inhibitor CHEBI:141153
fungicide CHEBI:24127
antifungal agent CHEBI:35718
antifungal agrochemical CHEBI:86328

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
CHEBI	`CHEBI:83258`	fenamidone	`antibioticmech:chebi-7b388617f7`	2026-08-30

Mechanism summary

Mode of action: ENERGY_METABOLISM_INHIBITION host shared target — Assigned from ChEBI role CHEBI:141153 (quinone outside inhibitor), CHEBI:38499 (mitochondrial cytochrome-bc1 complex inhibitor). ChEBI asserts the role on the compound. The target it names is one the host has too, so the mechanism is true but is not evidence of selectivity — see mode_of_action_target_scope. Not a curator's mechanistic review.

Curation history

SEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Seeded from data/raw/ inventories (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 2026-09-10 · 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).

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