AntibioticMech

carboxin

CHEBI:3405 ·resolve ·ANTIFUNGAL ·EXACT SEEDED

An anilide obtained by formal condensation of the amino group of aniline with the carboxy group of 2-methyl-5,6-dihydro-1,4-oxathiine-3-carboxylic acid. A fungicide for control of bunts and smuts that is normally used as a seed treatment. — ChEBI

Classification

Strictly broader compounds or drug classes this molecule belongs to.

• CHEBI:13248 CHEBI:13248
• CHEBI:140325 CHEBI:140325
• CHEBI:38104 CHEBI:38104
• CHEBI:38106 CHEBI:38106
• CHEBI:51751 CHEBI:51751
• CHEBI:87015 CHEBI:87015

Chemical structure

Computed structure properties

Molecular formula	C12H13NO2S
Charge	0
Average mass	235.308 Da
Monoisotopic mass	235.0667 Da
Source	ChEBI
InChIKey	GYSSRZJIHXQEHQ-UHFFFAOYSA-N

SMILES

CC1=C(C(=O)Nc2ccccc2)SCCO1

InChI

InChI=1S/C12H13NO2S/c1-9-11(16-8-7-15-9)12(14)13-10-5-3-2-4-6-10/h2-6H,7-8H2,1H3,(H,13,14)

Also called

• 2-methyl-N-phenyl-5,6-dihydro-1,4-oxathiine-3-carboxamide (EXACT_SYNONYM)— chebi
• 2,3-Dihydro-5-carboxanilido-6-methyl-1,4-oxathiin (EXACT_SYNONYM)— chebi
• 2,3-Dihydro-6-methyl-1,4-oxathiin-5-carboxanilide (EXACT_SYNONYM)— chebi
• 2,3-Dihydro-6-methyl-5-phenylcarbamoyl-1,4-oxathiin (EXACT_SYNONYM)— chebi
• 5,6-Dihydro-2-methyl-1,4-oxathiin-3-carboxanilide (EXACT_SYNONYM)— chebi
• 5,6-Dihydro-2-methyl-3-carboxanilido-1,4-oxathiin (EXACT_SYNONYM)— chebi
• 5,6-Dihydro-2-methyl-N-phenyl-1,4-oxathiin-3-carboxamide (EXACT_SYNONYM)— chebi
• 5-Carboxanilido-2,3-dihydro-6-methyl-1,4-oxathiin (EXACT_SYNONYM)— chebi
• Carbathiin (EXACT_SYNONYM)— chebi
• Carboxine (EXACT_SYNONYM)— chebi
• oxatin (EXACT_SYNONYM)— chebi

Cross-references

Equivalent identifiers for this same structure in other resources.

• cas:5234-68-4
• kegg.compound:C11255
• lincs.smallmolecule:LSM-25660
• metacyc.compound:CPD0-1366
• patent:EP0042182
• pdb-ccd:CBE
• pesticides:carboxin
• ppdb:122
• reaxys:983249

Activity roles

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

• CHEBI:24127 CHEBI:24127
• CHEBI:35718 CHEBI:35718
• CHEBI:86328 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:3405	carboxin	antibioticmech:chebi-ebea524080	2026-08-30

Mechanism summary

Mode of action

ENERGY_METABOLISM_INHIBITION host shared target — Assigned from ChEBI role CHEBI:83072 (EC 1.3.5.1 [succinate dehydrogenase (quinone)] 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

36 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.

UNKNOWN 36

UNKNOWN

Determinant	ARO ID	Organism	Gene families	Evidence
Mosdi1(H245L) (amino acid mutation) [Not assayed] associated with resistance to carboxin This is a curated gene-alteration/chemical resistance association, not evidence for a specific biochemical resistance mechanism.	—	Magnaporthe oryzae NCBITaxon:318829 strain Guy11 NCBITaxon:242507 UniProtKB:G4NE45 PHIPO:0000377	—	PMID:27558019 (PHI-base primary-literature antimicrobial interaction PHIG:9109; joined to this record by exact ChEBI identifier.) Cell growth assay
SDH2 transformant(Cbx02-SDH2(H267Y)) (transformant) [Ectopic] associated with resistance to carboxin This is a curated gene-alteration/chemical resistance association, not evidence for a specific biochemical resistance mechanism.	—	Zymoseptoria tritici NCBITaxon:1047171 strain Unknown strain UniProtKB:O42772 PHIPO:0000377	—	PMID:9871122 (PHI-base primary-literature antimicrobial interaction PHIG:4137; joined to this record by exact ChEBI identifier.) Cell growth assay
SDH2(H253L) (amino acid mutation) [Ectopic] associated with resistance to carboxin This is a curated gene-alteration/chemical resistance association, not evidence for a specific biochemical resistance mechanism.	—	Ustilago maydis NCBITaxon:5270 strain IMI103761 UniProtKB:P32420 KIS70918 PHIPO:0000377	—	PMID:1423716 (PHI-base primary-literature antimicrobial interaction PHIG:9367; joined to this record by exact ChEBI identifier.) Cell growth assay
SDHB transformant(Cbx1-SDHB(I269V)) (transformant) [Not assayed] associated with resistance to carboxin This is a curated gene-alteration/chemical resistance association, not evidence for a specific biochemical resistance mechanism.	—	Zymoseptoria tritici NCBITaxon:1047171 strain IPO323 UniProtKB:O42772 PHIPO:0000377	—	PMID:22536383 (PHI-base primary-literature antimicrobial interaction PHIG:4137; joined to this record by exact ChEBI identifier.) Cell growth assay
SDHB transformant(Cbx28-SDHB(H267Y)) (transformant) [Not assayed] associated with resistance to carboxin This is a curated gene-alteration/chemical resistance association, not evidence for a specific biochemical resistance mechanism.	—	Zymoseptoria tritici NCBITaxon:1047171 strain IPO323 UniProtKB:O42772 PHIPO:0000377	—	PMID:22536383 (PHI-base primary-literature antimicrobial interaction PHIG:4137; joined to this record by exact ChEBI identifier.) Cell growth assay
SDHB transformant(Cbx29-SDHB(H267L)) (transformant) [Not assayed] associated with resistance to carboxin This is a curated gene-alteration/chemical resistance association, not evidence for a specific biochemical resistance mechanism.	—	Zymoseptoria tritici NCBITaxon:1047171 strain IPO323 UniProtKB:O42772 PHIPO:0000377	—	PMID:22536383 (PHI-base primary-literature antimicrobial interaction PHIG:4137; joined to this record by exact ChEBI identifier.) Cell growth assay
SDHB transformant(Cbx56-SDHB(R265P)) (transformant) [Not assayed] associated with resistance to carboxin This is a curated gene-alteration/chemical resistance association, not evidence for a specific biochemical resistance mechanism.	—	Zymoseptoria tritici NCBITaxon:1047171 strain IPO323 UniProtKB:O42772 PHIPO:0000377	—	PMID:22536383 (PHI-base primary-literature antimicrobial interaction PHIG:4137; joined to this record by exact ChEBI identifier.) Cell growth assay
SDHC transformant(Izm1-SDHC(H152R)) (transformant) [Not assayed] associated with resistance to carboxin This is a curated gene-alteration/chemical resistance association, not evidence for a specific biochemical resistance mechanism.	—	Zymoseptoria tritici NCBITaxon:1047171 strain IPO323 NCBITaxon:336722 UniProtKB:F9XH52 PHIPO:0000377	—	PMID:22536383 (PHI-base primary-literature antimicrobial interaction PHIG:9475; joined to this record by exact ChEBI identifier.) Cell growth assay
SDHC transformant(Izm7-SDHC(N86K)) (transformant) [Not assayed] associated with resistance to carboxin This is a curated gene-alteration/chemical resistance association, not evidence for a specific biochemical resistance mechanism.	—	Zymoseptoria tritici NCBITaxon:1047171 strain IPO323 NCBITaxon:336722 UniProtKB:F9XH52 PHIPO:0000377	—	PMID:22536383 (PHI-base primary-literature antimicrobial interaction PHIG:9475; joined to this record by exact ChEBI identifier.) Cell growth assay
SDHD transformant(Cbx67-SDHD(D129G)) (transformant) [Not assayed] associated with resistance to carboxin This is a curated gene-alteration/chemical resistance association, not evidence for a specific biochemical resistance mechanism.	—	Zymoseptoria tritici NCBITaxon:1047171 strain IPO323 NCBITaxon:336722 UniProtKB:F9X9V6 PHIPO:0000377	—	PMID:22536383 (PHI-base primary-literature antimicrobial interaction PHIG:9472; joined to this record by exact ChEBI identifier.) Cell growth assay
SdhB transformant(JK19R1-SdhB(A11V)) (transformant) [Not assayed] associated with resistance to carboxin This is a curated gene-alteration/chemical resistance association, not evidence for a specific biochemical resistance mechanism.	—	Sclerotinia sclerotiorum NCBITaxon:5180 strain JK19 NCBITaxon:665079 UniProtKB:A7EGE3 PHIPO:0000377	—	PMID:25441450 (PHI-base primary-literature antimicrobial interaction PHIG:5032; joined to this record by exact ChEBI identifier.) Cell growth assay
SdhB(C137R) (amino acid mutation) [Not assayed] associated with resistance to carboxin This is a curated gene-alteration/chemical resistance association, not evidence for a specific biochemical resistance mechanism.	—	Zymoseptoria tritici NCBITaxon:1047171 strain IPO323 UniProtKB:O42772 PHIPO:0000377	—	PMID:21933337 (PHI-base primary-literature antimicrobial interaction PHIG:4137; joined to this record by exact ChEBI identifier.) Cell growth assay
SdhB(H267F) (amino acid mutation) [Not assayed] associated with resistance to carboxin This is a curated gene-alteration/chemical resistance association, not evidence for a specific biochemical resistance mechanism.	—	Zymoseptoria tritici NCBITaxon:1047171 strain IPO323 UniProtKB:O42772 PHIPO:0000377	—	PMID:21933337 (PHI-base primary-literature antimicrobial interaction PHIG:4137; joined to this record by exact ChEBI identifier.) Cell growth assay
SdhB(H267L) (amino acid mutation) [Not assayed] associated with resistance to carboxin This is a curated gene-alteration/chemical resistance association, not evidence for a specific biochemical resistance mechanism.	—	Zymoseptoria tritici NCBITaxon:1047171 strain IPO323 UniProtKB:O42772 PHIPO:0000377	—	PMID:21933337 (PHI-base primary-literature antimicrobial interaction PHIG:4137; joined to this record by exact ChEBI identifier.) Cell growth assay
SdhB(H267L) (amino acid mutation) [Not assayed] associated with resistance to carboxin This is a curated gene-alteration/chemical resistance association, not evidence for a specific biochemical resistance mechanism.	—	Zymoseptoria tritici NCBITaxon:1047171 strain IPO323 UniProtKB:O42772 PHIPO:0000377	—	PMID:26092798 (PHI-base primary-literature antimicrobial interaction PHIG:4137; joined to this record by exact ChEBI identifier.) Cell growth assay
SdhB(H267N) (amino acid mutation) [Not assayed] associated with resistance to carboxin This is a curated gene-alteration/chemical resistance association, not evidence for a specific biochemical resistance mechanism.	—	Zymoseptoria tritici NCBITaxon:1047171 strain IPO323 UniProtKB:O42772 PHIPO:0000377	—	PMID:21933337 (PHI-base primary-literature antimicrobial interaction PHIG:4137; joined to this record by exact ChEBI identifier.) Cell growth assay
SdhB(H267N) (amino acid mutation) [Not assayed] associated with resistance to carboxin This is a curated gene-alteration/chemical resistance association, not evidence for a specific biochemical resistance mechanism.	—	Zymoseptoria tritici NCBITaxon:1047171 strain IRE30 UniProtKB:O42772 PHIPO:0000377	—	PMID:21933337 (PHI-base primary-literature antimicrobial interaction PHIG:4137; joined to this record by exact ChEBI identifier.) Cell growth assay
SdhB(H267Y) (amino acid mutation) [Not assayed] associated with resistance to carboxin This is a curated gene-alteration/chemical resistance association, not evidence for a specific biochemical resistance mechanism.	—	Zymoseptoria tritici NCBITaxon:1047171 strain IRE30 UniProtKB:O42772 PHIPO:0000377	—	PMID:21933337 (PHI-base primary-literature antimicrobial interaction PHIG:4137; joined to this record by exact ChEBI identifier.) Cell growth assay
SdhB(H267Y) (amino acid mutation) [Not assayed] associated with resistance to carboxin This is a curated gene-alteration/chemical resistance association, not evidence for a specific biochemical resistance mechanism.	—	Zymoseptoria tritici NCBITaxon:1047171 strain IPO323 UniProtKB:O42772 PHIPO:0000377	—	PMID:21933337 (PHI-base primary-literature antimicrobial interaction PHIG:4137; joined to this record by exact ChEBI identifier.) Cell growth assay
SdhB(I269V) (amino acid mutation) [Not assayed] associated with resistance to carboxin This is a curated gene-alteration/chemical resistance association, not evidence for a specific biochemical resistance mechanism.	—	Zymoseptoria tritici NCBITaxon:1047171 strain IPO323 UniProtKB:O42772 PHIPO:0000377	—	PMID:21933337 (PHI-base primary-literature antimicrobial interaction PHIG:4137; joined to this record by exact ChEBI identifier.) Cell growth assay
SdhB(N224I) (amino acid mutation) [Not assayed] associated with resistance to carboxin This is a curated gene-alteration/chemical resistance association, not evidence for a specific biochemical resistance mechanism.	—	Ramularia collo-cygni NCBITaxon:112498 strain DK05 UniProtKB:A0A1S6KZ79 PHIPO:0000377	—	PMID:27644008 (PHI-base primary-literature antimicrobial interaction PHIG:3434; joined to this record by exact ChEBI identifier.) Cell growth assay
SdhB(P155L, H267Y) (amino acid mutation) [Not assayed] associated with resistance to carboxin This is a curated gene-alteration/chemical resistance association, not evidence for a specific biochemical resistance mechanism.	—	Zymoseptoria tritici NCBITaxon:1047171 strain IRE30 UniProtKB:O42772 PHIPO:0000377	—	PMID:21933337 (PHI-base primary-literature antimicrobial interaction PHIG:4137; joined to this record by exact ChEBI identifier.) Cell growth assay
SdhB(R265P) (amino acid mutation) [Not assayed] associated with resistance to carboxin This is a curated gene-alteration/chemical resistance association, not evidence for a specific biochemical resistance mechanism.	—	Zymoseptoria tritici NCBITaxon:1047171 strain IPO323 UniProtKB:O42772 PHIPO:0000377	—	PMID:21933337 (PHI-base primary-literature antimicrobial interaction PHIG:4137; joined to this record by exact ChEBI identifier.) Cell growth assay
SdhB(S221P) (amino acid mutation) [Not assayed] associated with resistance to carboxin This is a curated gene-alteration/chemical resistance association, not evidence for a specific biochemical resistance mechanism.	—	Zymoseptoria tritici NCBITaxon:1047171 strain IPO323 UniProtKB:O42772 PHIPO:0000377	—	PMID:21933337 (PHI-base primary-literature antimicrobial interaction PHIG:4137; joined to this record by exact ChEBI identifier.) Cell growth assay
SdhB(S221P) (amino acid mutation) [Not assayed] associated with resistance to carboxin This is a curated gene-alteration/chemical resistance association, not evidence for a specific biochemical resistance mechanism.	—	Zymoseptoria tritici NCBITaxon:1047171 strain IRE30 UniProtKB:O42772 PHIPO:0000377	—	PMID:21933337 (PHI-base primary-literature antimicrobial interaction PHIG:4137; joined to this record by exact ChEBI identifier.) Cell growth assay
SdhB(S221T) (amino acid mutation) [Not assayed] associated with resistance to carboxin This is a curated gene-alteration/chemical resistance association, not evidence for a specific biochemical resistance mechanism.	—	Zymoseptoria tritici NCBITaxon:1047171 strain IPO323 UniProtKB:O42772 PHIPO:0000377	—	PMID:21933337 (PHI-base primary-literature antimicrobial interaction PHIG:4137; joined to this record by exact ChEBI identifier.) Cell growth assay
SdhC(H142Q) (amino acid mutation) [Not assayed] associated with resistance to carboxin This is a curated gene-alteration/chemical resistance association, not evidence for a specific biochemical resistance mechanism.	—	Ramularia collo-cygni NCBITaxon:112498 strain DK05 UniProtKB:A0A1S6KZ87 PHIPO:0000377	—	PMID:27644008 (PHI-base primary-literature antimicrobial interaction PHIG:3435; joined to this record by exact ChEBI identifier.) Cell growth assay
SdhC(H142R) (amino acid mutation) [Not assayed] associated with resistance to carboxin This is a curated gene-alteration/chemical resistance association, not evidence for a specific biochemical resistance mechanism.	—	Ramularia collo-cygni NCBITaxon:112498 strain DK05 UniProtKB:A0A1S6KZ87 PHIPO:0000377	—	PMID:27644008 (PHI-base primary-literature antimicrobial interaction PHIG:3435; joined to this record by exact ChEBI identifier.) Cell growth assay
SdhC(L85P) (amino acid mutation) [Not assayed] associated with resistance to carboxin This is a curated gene-alteration/chemical resistance association, not evidence for a specific biochemical resistance mechanism.	—	Zymoseptoria tritici NCBITaxon:1047171 strain IPO323 NCBITaxon:336722 UniProtKB:F9XH52 PHIPO:0000377	—	PMID:21933337 (PHI-base primary-literature antimicrobial interaction PHIG:9475; joined to this record by exact ChEBI identifier.) Cell growth assay
SdhC(N86K) (amino acid mutation) [Not assayed] associated with resistance to carboxin This is a curated gene-alteration/chemical resistance association, not evidence for a specific biochemical resistance mechanism.	—	Zymoseptoria tritici NCBITaxon:1047171 strain IPO323 NCBITaxon:336722 UniProtKB:F9XH52 PHIPO:0000377	—	PMID:21933337 (PHI-base primary-literature antimicrobial interaction PHIG:9475; joined to this record by exact ChEBI identifier.) Cell growth assay
SdhD(D129E) (amino acid mutation) [Not assayed] associated with resistance to carboxin This is a curated gene-alteration/chemical resistance association, not evidence for a specific biochemical resistance mechanism.	—	Zymoseptoria tritici NCBITaxon:1047171 strain IRE30 NCBITaxon:336722 UniProtKB:F9X9V6 PHIPO:0000377	—	PMID:21933337 (PHI-base primary-literature antimicrobial interaction PHIG:9472; joined to this record by exact ChEBI identifier.) Cell growth assay
SdhD(D129E) (amino acid mutation) [Not assayed] associated with resistance to carboxin This is a curated gene-alteration/chemical resistance association, not evidence for a specific biochemical resistance mechanism.	—	Zymoseptoria tritici NCBITaxon:1047171 strain IPO323 NCBITaxon:336722 UniProtKB:F9X9V6 PHIPO:0000377	—	PMID:21933337 (PHI-base primary-literature antimicrobial interaction PHIG:9472; joined to this record by exact ChEBI identifier.) Cell growth assay
SdhD(D129T) (amino acid mutation) [Not assayed] associated with resistance to carboxin This is a curated gene-alteration/chemical resistance association, not evidence for a specific biochemical resistance mechanism.	—	Zymoseptoria tritici NCBITaxon:1047171 strain IPO323 NCBITaxon:336722 UniProtKB:F9X9V6 PHIPO:0000377	—	PMID:21933337 (PHI-base primary-literature antimicrobial interaction PHIG:9472; joined to this record by exact ChEBI identifier.) Cell growth assay
SdhD(I127V) (amino acid mutation) [Not assayed] associated with resistance to carboxin This is a curated gene-alteration/chemical resistance association, not evidence for a specific biochemical resistance mechanism.	—	Zymoseptoria tritici NCBITaxon:1047171 strain IPO323 NCBITaxon:336722 UniProtKB:F9X9V6 PHIPO:0000377	—	PMID:21933337 (PHI-base primary-literature antimicrobial interaction PHIG:9472; joined to this record by exact ChEBI identifier.) Cell growth assay
sdhB transformant(CR9-sdhB(H249L)) (transformant) [Ectopic] associated with resistance to carboxin This is a curated gene-alteration/chemical resistance association, not evidence for a specific biochemical resistance mechanism.	—	Aspergillus oryzae NCBITaxon:5062 strain RIB40 NCBITaxon:510516 UniProtKB:Q2TWM0 PHIPO:0000377	—	PMID:18992352 (PHI-base primary-literature antimicrobial interaction PHIG:8700; joined to this record by exact ChEBI identifier.) Cell growth assay
sdhC transformant(CR6-sdhC(T90I)) (transformant) [Ectopic] associated with resistance to carboxin This is a curated gene-alteration/chemical resistance association, not evidence for a specific biochemical resistance mechanism.	—	Aspergillus oryzae NCBITaxon:5062 strain RIB40 NCBITaxon:510516 UniProtKB:Q2U3V9 PHIPO:0000377	—	PMID:18992352 (PHI-base primary-literature antimicrobial interaction PHIG:8701; joined to this record by exact ChEBI identifier.) Cell growth assay

Curation history

1. SEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources

   Seeded from data/raw/ inventories (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 2026-09-02 · 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 2026-09-03 · 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.