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thiolutin

CHEBI:156450 ·resolve ·ANTIBACTERIAL ·EXACT SEEDED

A dithiolopyrrolone antibiotic that is 4,5-dihydro[1,2]dithiolo[4,3-b]pyrrole in which the hydrogens at positions 4,5 and 6 have been replaced by methyl, oxo and acetamido groups, respectively. It is a potent inhibitor of RNA polymerases, inhibits the angiogenesis of human umbilical vein endothelial cells, and also inhibits JAMM metalloproteases. — 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.

Chemical structure

Computed structure properties
Molecular formulaC8H8N2O2S2
Charge0
Average mass228.298 Da
Monoisotopic mass228.00272 Da
SourceChEBI
InChIKeyMHMRAFONCSQAIA-UHFFFAOYSA-N

SMILES

CC(=O)Nc1c2sscc-2n(C)c1=O

InChI

InChI=1S/C8H8N2O2S2/c1-4(11)9-6-7-5(3-13-14-7)10(2)8(6)12/h3H,1-2H3,(H,9,11)

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
CHEBI CHEBI:156450 thiolutin antibioticmech:chebi-4e6261f444 2026-08-30

Mechanism summary

Mode of action
MULTIPLE host shared target — Assigned from ChEBI roles CHEBI:37416 (EC 2.7.7.6 (RNA polymerase) inhibitor), CHEBI:48001 (protein synthesis inhibitor), which map to NUCLEIC_ACID_SYNTHESIS_INHIBITION, PROTEIN_SYNTHESIS_INHIBITION. ChEBI asserts these roles on the compound; a curator should decide whether one is primary. 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

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

UNKNOWN 4
UNKNOWN
DeterminantARO IDOrganismGene familiesEvidence
Combined TRX1/TRX2 loss-associated thiolutin resistance in laboratory yeast
Combined-loss phenotype, not two independent single-gene resistance effects. The CKY457-derived background is distinct from a reference strain accession. Table S2 lists CKY1984 and CKY1985; the plotted row does not identify which derivative. Direct reduction of thiolutin by either protein remains an author hypothesis. No exact experimental protein, allele, strain TaxID, genome, MIC or clinical category assigned. Mechanistic interpretations are not direct biochemical measurements.		 — Saccharomyces cerevisiae NCBITaxon:4932 TRX1, TRX2
  • PMID:38214235 (Results on thioredoxins; Supplementary Figure S1G; Table S2, Yeast Strains rows 27-28; DOI:10.1093/nar/gkad1258. Selected native supplemental figures and tables inspected; one study, not independent studies.)
  • UniProtKB:P22217 (Reference identity only: TRX1, YLR043C, S288c NCBITaxon:559292; UniProtKB 2026_03, entry 219, sequence 3. Not an experimental allele assignment.)
  • UniProtKB:P22803 (Reference identity only: TRX2, YGR209C, S288c NCBITaxon:559292; UniProtKB 2026_03, entry 230, sequence 3. Not an experimental allele assignment.)
Comparative plate growth
SNQ2-associated thiolutin resistance in laboratory yeast
Plasmid-dependent, dominant-or-dosage-associated phenotype. Table S1 candidates 220 and 221 have identical reported synonymous changes and are not distinct protein alleles. A dosage contribution is not excluded. SNQ2 deletion increased sensitivity, not resistance; direct thiolutin transport was not measured in these growth assays. No exact experimental protein, allele, strain TaxID, genome, MIC or clinical category assigned. Mechanistic interpretations are not direct biochemical measurements.		 — Saccharomyces cerevisiae NCBITaxon:4932 SNQ2
  • PMID:38214235 (Results on MDR/OSR; Supplementary Figures S1B, S1E and S3; Table S1 rows 5-6 and note 2; DOI:10.1093/nar/gkad1258. Selected native supplemental figures and tables inspected; one study, not independent studies.)
  • UniProtKB:P32568 (Reference identity only: SNQ2, YDR011W, S288c NCBITaxon:559292; UniProtKB 2026_03, entry 216, sequence 2. Not an experimental allele assignment.)
Comparative plate growth
YAP1-associated thiolutin resistance in laboratory yeast
Mutant- or dosage-dependent resistance; gene presence alone is not predictive. Forward-screen CKY457 derivatives and Variomics candidates are distinct. Gene deletion did not reproduce the resistant phenotype. No exact experimental protein, allele, strain TaxID, genome, MIC or clinical category assigned. Mechanistic interpretations are not direct biochemical measurements.		 — Saccharomyces cerevisiae NCBITaxon:4932 YAP1
  • PMID:38214235 (Results on MDR/OSR; Supplementary Figures S1B, S1C, S1E and S3; Table S1 rows 9-10; DOI:10.1093/nar/gkad1258. Selected native supplemental figures and tables inspected; one study, not independent studies.)
  • UniProtKB:P19880 (Reference identity only: YAP1, YML007W, S288c NCBITaxon:559292; UniProtKB 2026_03, entry 230, sequence 2. Not an experimental allele assignment.)
Comparative plate growth
YRR1-associated thiolutin resistance in laboratory yeast
Mutant- or dosage-dependent resistance; gene presence alone is not predictive. Forward-screen CKY457 derivatives and Variomics candidates are distinct. Gene deletion did not reproduce the resistant phenotype. No exact experimental protein, allele, strain TaxID, genome, MIC or clinical category assigned. Mechanistic interpretations are not direct biochemical measurements.		 — Saccharomyces cerevisiae NCBITaxon:4932 YRR1
  • PMID:38214235 (Results on MDR/OSR; Supplementary Figures S1B, S1C, S1E and S3; Table S1 rows 16-17; DOI:10.1093/nar/gkad1258. Selected native supplemental figures and tables inspected; one study, not independent studies.)
  • UniProtKB:Q12172 (Reference identity only: YRR1, YOR162C, S288c NCBITaxon:559292; UniProtKB 2026_03, entry 169, sequence 1. Not an experimental allele assignment.)
Comparative plate growth

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 2026-09-10 · seed_from_sources

    Re-seeded from updated data/raw/ inventories

  5. RESEEDED_FROM_SOURCES 2026-09-10 · seed_from_sources

    Re-seeded from updated data/raw/ inventories

  6. CURATED_RESISTANCE_EVIDENCE 2026-10-12 · codex · LLM-assisted

    Added four qualitative thiolutin resistance associations from one laboratory-yeast study. Grounded species and five reference-only UniProt identities. Preserved dosage, duplicate-candidate, combined-loss and subject-identity limits. No exact alleles, genomes, numerical AST or clinical categories assigned; whole-record review remains open.

Provenance

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

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