pyrisoxazole

CHEBI:83823 ·resolve ·ANTIFUNGAL ·EXACT REVIEWED

A diastereoisomeric mixture of (3R,5S)- and (3R,5R)-pyrisoxazole. A novel isomeric fungicide primarily used for control of control tomato botrytis and also for fungal diseases of wheat and other crops. — ChEBI

Classification

Strictly broader compounds or drug classes this molecule belongs to.

Label unavailable CHEBI:60915

Chemical structure

Computed structure properties
Molecular formula	C16H17ClN2O
Charge	0
Average mass	288.778 Da
Monoisotopic mass	288.10294 Da
Source	ChEBI
InChIKey	DHTJFQWHCVTNRY-OEMAIJDKSA-N

SMILES

CN1OC(c2ccc(Cl)cc2)C[C@]1(C)c1cccnc1

InChI

InChI=1S/C16H17ClN2O/c1-16(13-4-3-9-18-11-13)10-15(20-19(16)2)12-5-7-14(17)8-6-12/h3-9,11,15H,10H2,1-2H3/t15?,16-/m1/s1

Also called

3-[(3R)-5-(4-chlorophenyl)-2,3-dimethyl-1,2-oxazolidin-3-yl]pyridine (EXACT_SYNONYM)— chebi
Dingjunezuo (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.

Activity roles

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

EC 1.14.13.70 (sterol 14α-demethylase) inhibitor CHEBI:77884
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:83823`	pyrisoxazole	`antibioticmech:chebi-01ffe69377`	2026-08-30

Molecular targets

The molecular entity or process this compound acts on. Each target carries evidence — this is a mechanistic claim, not a classification.

fungal CYP51 sterol 14-alpha-demethylase PROTEIN RESISTANCE_DETERMINANT

UV-induced and spontaneously selected resistant mutants, cross-resistance testing, CYP51 sequencing, and expression measurements; compound binding effects were assessed only by molecular docking. Evidence status: PRIMARY_EVIDENCE. Source: PRIMARY_LITERATURE 2020-06 (retrieved 2026-09-02).

Botrytis cinerea NCBITaxon:40559

Organism-specific examples
Protein	Gene	Organism	Entry
Sterol 14-alpha-demethylase `UniProtKB:A0A7G4P320` Botrytis cinerea ergosterol-biosynthesis CYP51 enzyme assayed for stereoselective binding and inhibition by pyrisoxazole isomers (PMID:32714305; species-level reference sequence context).	cyp51	Botrytis cinerea `NCBITaxon:40559`	UNREVIEWED

PMID:32714305 (Primary susceptibility, mutant-selection, sequencing, expression, and cross-resistance study.)

Mechanism summary

Mode of action: ERGOSTEROL_PATHWAY_INHIBITION host shared target — CURATOR: PMID:32714305 identified pyrisoxazole as a sterol 14-alpha-demethylase inhibitor, found cross-resistance only with other demethylase inhibitors, and linked resistant Botrytis cinerea mutants to CYP51 substitutions and induced CYP51 expression. Direct enzyme binding was modeled rather than experimentally measured, so the target is represented as a resistance determinant.

Resistance mechanisms

3 source-backed resistance determinants or associations, with ARO grounding where reported. Grouped by reported mechanism type.

ANTIBIOTIC_TARGET_ALTERATION 2

ANTIBIOTIC_TARGET_ALTERATION
Determinant	ARO ID	Organism	Gene families	Evidence
Botrytis cinerea CYP51 substitutions associated with pyrisoxazole resistance in RU-mutants Same-isolate association, not independent causal validation. Source numbering uses Zymoseptoria tritici CYP51 (AY253234), not a Botrytis UniProt sequence. No single-isolate protein assigned: Results names RU11-1, whereas Tables 1-3 name RU11-3.	—	Botrytis cinerea `NCBITaxon:40559`	CYP51 sterol 14-alpha-demethylase	PMID:32714305 (Results, Tables 1-3, and Figure 5.)
Botrytis cinerea RS10-1 CYP51 substitution associated with pyrisoxazole resistance Same-isolate association, not independent causal validation. M231T uses the paper's Zymoseptoria tritici CYP51 reference (AY253234), not UniProt sequence coordinates. UniProt cross-references the study's MT430876/QMT30302.1 and RS10-1; sequence version 1, unreviewed TrEMBL, release 2026_03, retrieved 2026-10-08 UTC. No strain TaxID or genome accession established.	—	Botrytis cinerea `NCBITaxon:40559` strain RS10-1 `UniProtKB:A0A7G4P320`	CYP51 sterol 14-alpha-demethylase	PMID:32714305 (Table 1 and Figure 5; molecular-analysis Results identify MT430876.) UniProtKB:A0A7G4P320 (Identifier crosswalk only; EMBL cross-reference and citation-specific strain annotation.)

OTHER 1

OTHER
Determinant	ARO ID	Organism	Gene families	Evidence
induced CYP51 expression in pyrisoxazole-resistant isolates Pyrisoxazole exposure induced higher CYP51 expression in resistant than sensitive isolates.	—	Botrytis cinerea `NCBITaxon:40559`	CYP51 sterol 14-alpha-demethylase	PMID:32714305 (Figure 6; expression association, not proof of independent causation.)

Record-level evidence

PMID:32714305 (Primary compound-specific target-associated resistance study.)

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 2026-08-30 · seed_from_sources
Re-seeded from updated data/raw/ inventories
REVIEWED 2026-09-02 · codex · LLM-assisted
Verified the exact ChEBI mixture identity, structure representation, and antifungal class; curator-confirmed the demethylase-pathway mode and added CYP51 resistance-determinant, mutation, and expression evidence.
GROUNDED_RESISTANCE_CONTEXT 2026-10-08 · codex · LLM-assisted
Separated curator-owned study groups; grounded the supported protein/taxon crosswalk and preserved unresolved numbering and isolate-name limitations. No activity measurements or source-owned assertions changed.
CURATED_UNIPROT_PROTEIN_EXAMPLES 2026-10-18 · antigravity · LLM-assisted
Added curated Botrytis cinerea CYP51 sterol 14-alpha-demethylase (A0A7G4P320) UniProtKB protein example on the PRIMARY_LITERATURE fungal CYP51 sterol 14-alpha-demethylase molecular target.

Provenance

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

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