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azoxystrobin

CHEBI:40909 ·resolve ·ANTIFUNGAL ·EXACT SEEDED

An aryloxypyrimidine having a 4,6-diphenoxypyrimidine skeleton in which one of the phenyl rings is cyano-substituted at C-2 and the other carries a 2-methoxy-1-(methoxycarbonyl)vinyl substituent, also at C-2. An inhibitor of mitochondrial respiration by blocking electron transfer between cytochromes b and c1, it is used widely as a fungicide in agriculture. — 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

strobilurin fungicideARO:3009305

Strictly broader compounds or drug classes this molecule belongs to.

Chemical structure

Computed structure properties
Molecular formulaC22H17N3O5
Charge0
Average mass403.394 Da
Monoisotopic mass403.11682 Da
SourceChEBI
InChIKeyWFDXOXNFNRHQEC-GHRIWEEISA-N

SMILES

CO/C=C(/C(=O)OC)c1ccccc1Oc1cc(Oc2ccccc2C#N)ncn1

InChI

InChI=1S/C22H17N3O5/c1-27-13-17(22(26)28-2)16-8-4-6-10-19(16)30-21-11-20(24-14-25-21)29-18-9-5-3-7-15(18)12-23/h3-11,13-14H,1-2H3/b17-13+

Also called

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.

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
SourceNative IDLabelMinted CURIEVersion
ARO ARO:3009185 azoxystrobin antibioticmech:aro-5dac57f915 2026-08-30
CHEBI CHEBI:40909 azoxystrobin antibioticmech:chebi-c78e11ac97 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.

Resistance mechanisms

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

ANTIBIOTIC_TARGET_ALTERATION 6
ANTIBIOTIC_TARGET_ALTERATION
DeterminantARO IDOrganismGene familiesEvidence
Aspergillus fumigatus Cyp51A with mutations conferring resistance to azoxystrobin ARO:3009545 not organism-specific —
  • ARO:3009545 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3009185 (azoxystrobin); database assertion, not a primary citation.)
Aspergillus fumigatus beta-tubulin with mutations conferring resistance to azoxystrobin ARO:3009480 not organism-specific —
  • ARO:3009480 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3009185 (azoxystrobin); database assertion, not a primary citation.)
Colletotrichum gloeosporioides cytochrome b protein with mutations conferring resistance to azoxystrobin ARO:3009275 not organism-specific —
  • ARO:3009275 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3009185 (azoxystrobin); database assertion, not a primary citation.)
Colletotrichum graminicola cytochrome b protein with mutations associated with resistance to azoxystrobin ARO:3009280 not organism-specific —
  • ARO:3009280 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3009185 (azoxystrobin); database assertion, not a primary citation.)
Colletotrichum siamense beta-tubulin with mutations conferring resistance to azoxystrobin ARO:3009471 not organism-specific —
  • ARO:3009471 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3009185 (azoxystrobin); database assertion, not a primary citation.)
Colletotrichum siamense cytochrome b protein with mutations associated with resistance to azoxystrobin ARO:3009279 not organism-specific —
  • ARO:3009279 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3009185 (azoxystrobin); database assertion, not a primary citation.)
UNKNOWN 5
UNKNOWN
DeterminantARO IDOrganismGene familiesEvidence
Mdm10delta (deletion) associated with resistance to azoxystrobin
This is a curated gene-alteration/chemical resistance association, not evidence for a specific biochemical resistance mechanism. Grounding review fungal-2025-azoxystrobin-parent-context: M3125 is the parent background, distinct from the tested derivatives. W7MZ22 and TaxID 334819 identify M3125 / FGSC 7600 reference context, not an exact experimental allele or derivative. Table 1 reports EC50, not MIC; no clinical interpretation or activity measurement is inferred. Source labels and biological fields are retained. Exact subject protein, strain TaxID and genome remain unresolved. Reference-only source identifiers: strain_taxon_id=NCBITaxon:334819; protein_accession=UniProtKB:W7MZ22.		 — Fusarium verticillioides NCBITaxon:117187
strain M3125
PHIPO:0000388		 —
  • PMID:40934067 (PHI-base primary-literature antimicrobial interaction PHIG:10867; joined to this record by exact ChEBI identifier.)
  • DOI:10.1080/21505594.2025.2555419 (Identifier-scope review: Results section s0003-s2006: separate parental and derivative comparisons; Table 1, UniProtKB release 2026_03: W7MZ22 entry 46, sequence version 1; M3125 / FGSC 7600 reference taxonomy. Reviewed 2026-10-08 by codex; curation/phibase_grounding_reviews.json SHA-256 1f5d50346b2916fce10969afa8d6409ea836dd15e8cf7fe3cfa3a78d6289b4ed.)
Cell growth assay
Pks1delta (deletion) associated with resistance to azoxystrobin
This is a curated gene-alteration/chemical resistance association, not evidence for a specific biochemical resistance mechanism. Grounding review fungal-2026-p1-reference-context: P1 is the parental background, not a unique tested derivative. A0A8E5ME34 carries species-level taxonomy and a reference locus, not an independently established P1-derived experimental allele. The paper's IC50 endpoint is not converted to MIC. Source labels and biological fields remain unchanged; no new protein, TaxID, genome or activity measurement is assigned. Reference-only source identifiers: protein_accession=UniProtKB:A0A8E5ME34.		 — Ustilaginoidea virens NCBITaxon:1159556
strain P1
PHIPO:0000388		 —
  • PMID:41745253 (PHI-base primary-literature antimicrobial interaction PHIG:11363; joined to this record by exact ChEBI identifier.)
  • DOI:10.3390/jof12020111 (Identifier-scope review: Results section sec3dot5dot5-jof-12-00111: separate parental and derivative comparisons; Table 1, Parent identity in sec2dot1-jof-12-00111, UniProtKB release 2026_03: A0A8E5ME34 entry 17, sequence version 1; species-level taxonomy and reference locus. Reviewed 2026-10-08 by codex; curation/phibase_grounding_reviews.json SHA-256 1f5d50346b2916fce10969afa8d6409ea836dd15e8cf7fe3cfa3a78d6289b4ed.)
Cell growth assay
cytb(G143A) (amino acid mutation) [Not assayed] associated with resistance to azoxystrobin
This is a curated gene-alteration/chemical resistance association, not evidence for a specific biochemical resistance mechanism.		 — Magnaporthe oryzae NCBITaxon:318829
strain 4091-5-8
UniProtKB:A0A089QDC9
PHIPO:0000388		 —
  • PMID:12612806 (PHI-base primary-literature antimicrobial interaction PHIG:9043; joined to this record by exact ChEBI identifier.)
Cell growth assay
cytb(G143S) (amino acid mutation) [Not assayed] associated with resistance to azoxystrobin
This is a curated gene-alteration/chemical resistance association, not evidence for a specific biochemical resistance mechanism.		 — Magnaporthe oryzae NCBITaxon:318829
strain 4091-5-8
UniProtKB:A0A089QDC9
PHIPO:0000388		 —
  • PMID:12612806 (PHI-base primary-literature antimicrobial interaction PHIG:9043; joined to this record by exact ChEBI identifier.)
Cell growth assay
tubA(M233I) (amino acid mutation) [Not assayed] associated with resistance to azoxystrobin
This is a curated gene-alteration/chemical resistance association, not evidence for a specific biochemical resistance mechanism. Grounding review fungal-2015-azoxystrobin-cooccurrence-context: NJ11 is the parent background, distinct from the separately tested derivatives. The paper reports azoxystrobin-resistant isolates in all tested phenotype groups, including the parent; this co-occurrence does not establish an allele-specific azoxystrobin effect. P53373 is source-reference context, not an exact subject allele. Source biological fields are retained but not independently validated by this identity review. EC50 is not MIC; no activity measurement or genome is assigned. Reference-only source identifiers: protein_accession=UniProtKB:P53373.		 — Botrytis cinerea NCBITaxon:40559
strain NJ11
PHIPO:0000388		 —
  • PMID:26596626 (PHI-base primary-literature antimicrobial interaction PHIG:2781; joined to this record by exact ChEBI identifier.)
  • DOI:10.1038/srep16881 (Identifier-scope review: Results: Cross resistance; Table 5, Results: parent versus separately tested derivatives, UniProtKB release 2026_03: P53373 entry 113, sequence version 1; species-level taxonomy and reference deposits. Reviewed 2026-10-08 by codex; curation/phibase_grounding_reviews.json SHA-256 1f5d50346b2916fce10969afa8d6409ea836dd15e8cf7fe3cfa3a78d6289b4ed.)
Cell growth assay

Curation history

  1. SEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources

    Seeded from data/raw/ inventories (ARO, CHEBI)

  2. RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources

    Re-seeded from updated data/raw/ inventories

  3. RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources

    Re-seeded from updated data/raw/ inventories

  4. RESEEDED_FROM_SOURCES 2026-09-02 · seed_from_sources

    Re-seeded from updated data/raw/ inventories

  5. RESEEDED_FROM_SOURCES 2026-09-03 · seed_from_sources

    Re-seeded from updated data/raw/ inventories

  6. RESEEDED_FROM_SOURCES 2026-09-03 · seed_from_sources

    Re-seeded from updated data/raw/ inventories

  7. RESEEDED_FROM_SOURCES 2026-09-10 · seed_from_sources

    Re-seeded from updated data/raw/ inventories

  8. REVIEWED_RESISTANCE_SUBJECT_CONTEXT 2026-10-08 · codex · LLM-assisted

    Scoped source protein and reference-strain identifiers to provenance after primary-paper review; parent labels, source biological claims and gene IDs retained. No experimental allele, genome or activity measurement inferred.

  9. REVIEWED_RESISTANCE_SUBJECT_CONTEXT 2026-10-08 · codex · LLM-assisted

    Refreshed the shared PHI-base review checksum after eight subject-identity corrections; previous decisions, biological fields and activities unchanged.

  10. REVIEWED_RESISTANCE_SUBJECT_CONTEXT 2026-10-08 · codex · LLM-assisted

    Refreshed shared PHI-base review checksum after the Darlington subject correction; prior review decisions, biological fields and activities unchanged.

  11. REVIEWED_RESISTANCE_SUBJECT_CONTEXT 2026-10-08 · codex · LLM-assisted

    Refreshed shared PHI-base review checksum after the Nakayama reference-scope review; prior decisions, biological fields and activities unchanged.

  12. REVIEWED_RESISTANCE_SUBJECT_CONTEXT 2026-10-08 · codex · LLM-assisted

    Refreshed shared PHI-base review checksum after the Duan reference-scope review; prior decisions, biological fields and activities unchanged.

  13. REVIEWED_RESISTANCE_SUBJECT_CONTEXT 2026-10-08 · codex · LLM-assisted

    Refreshed shared PHI-base review checksum after the Piotrowska parent-reference review; prior decisions, biological fields and activities unchanged.

  14. REVIEWED_RESISTANCE_SUBJECT_CONTEXT 2026-10-08 · codex · LLM-assisted

    Refreshed shared PHI-base review checksum after the Xu subject and species corrections; prior decisions, biological fields and activities unchanged.

  15. REVIEWED_RESISTANCE_SUBJECT_CONTEXT 2026-10-08 · codex · LLM-assisted

    Refreshed shared PHI-base review checksum after the Shima parent-reference review; prior decisions, biological fields and activities unchanged.

  16. REVIEWED_RESISTANCE_SUBJECT_CONTEXT 2026-10-08 · codex · LLM-assisted

    Refreshed shared PHI-base review checksum after the Mehrabi parent-reference review; prior decisions, biological fields and activities unchanged.

  17. REVIEWED_RESISTANCE_SUBJECT_CONTEXT 2026-10-08 · codex · LLM-assisted

    Refreshed shared PHI-base review checksum after the Huang parent-reference review; prior decisions, biological fields and activities unchanged.

  18. REVIEWED_RESISTANCE_SUBJECT_CONTEXT 2026-10-09 · codex · LLM-assisted

    Refreshed shared PHI-base review checksum after the HDF1 subject-reference review; prior decisions, biological fields and activities unchanged.

  19. REVIEWED_RESISTANCE_SUBJECT_CONTEXT 2026-10-09 · codex · LLM-assisted

    Refreshed shared PHI-base review checksum after the Fouche parent-cohort review; prior decisions, biological fields and activities unchanged.

  20. REVIEWED_RESISTANCE_REFERENCE_CONTEXT 2026-10-09 · codex · LLM-assisted

    Refreshed shared PHI-base review checksum after the SDH8 reference-alias correction; prior decisions, biological fields and activities unchanged.

  21. REVIEWED_RESISTANCE_SUBJECT_CONTEXT 2026-10-09 · codex · LLM-assisted

    Refreshed the shared PHI-base review checksum after the Posteraro subject-context review; previous decisions, biological fields and activities unchanged.

  22. REVIEWED_RESISTANCE_REFERENCE_CONTEXT 2026-10-12 · codex · LLM-assisted

    Refreshed the shared PHI-base review checksum after four reference-identifier scope corrections; previous decisions, biological fields and activities unchanged.

  23. REVIEWED_RESISTANCE_SUBJECT_CONTEXT 2026-10-13 · codex · LLM-assisted

    Refreshed the shared PHI-base review checksum after one Neurospora subject-context correction; previous decisions, biological fields and activities unchanged.

Provenance

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

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