holomycin

CHEBI:156451 ·resolve ·ANTIBACTERIAL ·EXACT REVIEWED

A dithiolopyrrolone antibiotic that is 4,5-dihydro[1,2]dithiolo[4,3-b]pyrrole in which the hydrogens at positions 5 and 6 have been replaced by oxo and acetamido groups, respectively. It is an inhibitor of DNA-dependent RNA polymerase, and exhibits antibacterial and antitumour properties. — ChEBI

Classification

Strictly broader compounds or drug classes this molecule belongs to.

• dithiolopyrrolone antibiotic CHEBI:156449
• Label unavailable CHEBI:22160

Chemical structure

SMILES

CC(=O)Nc1c2sscc-2nc1=O

InChI

InChI=1S/C7H6N2O2S2/c1-3(10)8-5-6-4(2-12-13-6)9-7(5)11/h2H,1H3,(H,8,10)(H,9,11)

Also called

• N-(5-oxo-4,5-dihydro[1,2]dithiolo[4,3-b]pyrrol-6-yl)acetamide (EXACT_SYNONYM)— chebi
• 6-(acetylamino)-1,2-dithiolo[4,3-b]pyrrol-5(4H)-one (EXACT_SYNONYM)— chebi
• 6-acetamido-1,2-dithiolo[4,3-b]pyrrol-5(4H)-one (EXACT_SYNONYM)— chebi
• N-(4,5-dihydro-5-oxo-1,2-dithiolo-[4,3-b]pyrrol-6-yl)acetamide (EXACT_SYNONYM)— chebi
• N-(5-oxo-4H-dithiolo[4,3-b]pyrrol-6-yl)acetamide (EXACT_SYNONYM)— chebi
• N-demethylthiolutin (EXACT_SYNONYM)— chebi
• N-{5-oxo-4H,5H-[1,2]dithiolo[4,3-b]pyrrol-6-yl}acetamide (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.

• cas:488-04-0
• metacyc.compound:CPD-17940
• reaxys:188430

Activity roles

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

• antimicrobial agent CHEBI:33281
• antibacterial agent CHEBI:33282
• antifungal agent CHEBI:35718

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.

Molecular targets

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

bacterial RNA synthesis and transcription elongation BIOLOGICAL_PROCESS DOWNSTREAM_AFFECTED_PROCESS

Whole-cell radiolabeling and induced beta-galactosidase kinetics supported rapid inhibition of bacterial transcription. Weak purified-polymerase inhibition did not establish RNA polymerase as the direct target. Evidence status: PRIMARY_EVIDENCE. Source: PRIMARY_LITERATURE 2001-02 (retrieved 2026-09-02).

Escherichia coli NCBITaxon:562

• PMID:11158751 (Primary holomycin whole-cell and purified-RNA-polymerase mechanism study (DOI:10.1128/AAC.45.2.532-539.2001).)

Mechanism summary

Mode of action

NUCLEIC_ACID_SYNTHESIS_INHIBITION microbial target — CURATOR: PMID:11158751 found rapid, bacteriostatic inhibition of RNA synthesis in Escherichia coli, independent of the RelA stringent response, and beta-galactosidase kinetics consistent with impaired RNA-chain elongation. Purified RNA polymerase was only weakly inhibited above growth-inhibitory concentrations, so the direct target remains unresolved and intracellular conversion to an active species remains possible.

Producer organisms

Organisms that biosynthesize this compound. Cluster link evidence is how the upstream source graded the gene cluster, so it is populated only for a source that grades it. An empty cell is not weaker support: a curator-authored producer carries its support in Evidence instead. Where the source entry named several compounds, the evidence is marked inherited, meaning it covers this compound together with the cluster's other products rather than singling it out. Those products need not be related to each other: a cluster can list an intermediate, a precursor and a finished antibiotic side by side.

Record-level evidence

• PMID:11158751 (Primary holomycin antibacterial spectrum and transcription-mechanism study.)

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. REVIEWED 2026-09-03 · codex · LLM-assisted

   Verified exact ChEBI identity, structure, antibiotic roles, and antibacterial class; curator-confirmed nucleic-acid-synthesis inhibition and added the measured transcription phenotype while retaining the unresolved direct-target gap.

5. RESEEDED_FROM_SOURCES 2026-09-08 · seed_from_sources

   Re-seeded from updated data/raw/ inventories

6. RESEEDED_FROM_SOURCES 2026-09-08 · 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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