bicozamycin

CHEBI:60584 ·resolve ·ANTIBACTERIAL ·EXACT REVIEWED

A commercially important azabicyclic antibiotic obtained from Streptomyces sapporonensis. It inhibits the Rho protein of E. coli. — ChEBI

Classification

bicyclomycin-like antibioticARO:3007150

Strictly broader compounds or drug classes this molecule belongs to.

Label unavailable CHEBI:35990
Label unavailable CHEBI:38295
bicyclomycin-like antibiotic ARO:3007150

Chemical structure

Computed structure properties
Molecular formula	C12H18N2O7
Charge	0
Average mass	302.283 Da
Monoisotopic mass	302.1114 Da
Source	ChEBI
InChIKey	WOUDXEYYJPOSNE-VKZDFBPFSA-N

SMILES

C=C1CCO[C@]2([C@@H](O)[C@@](C)(O)CO)NC(=O)[C@@]1(O)NC2=O

InChI

InChI=1S/C12H18N2O7/c1-6-3-4-21-12(7(16)10(2,19)5-15)9(18)13-11(6,20)8(17)14-12/h7,15-16,19-20H,1,3-5H2,2H3,(H,13,18)(H,14,17)/t7-,10-,11+,12-/m0/s1

Also called

bicozamicina (INN)— chebi
bicozamycine (INN)— chebi
bicozamycinum (INN)— chebi
Bicozamycin (EXACT_SYNONYM)— chebi
Bicyclomycin (EXACT_SYNONYM)— chebi
aizumycin (EXACT_SYNONYM)— chebi
Aizumycin (EXACT_SYNONYM)— aro
Bacfeed (EXACT_SYNONYM)— aro
Bacteron (EXACT_SYNONYM)— aro
Bicozamicina (EXACT_SYNONYM)— aro
Bicozamycine (EXACT_SYNONYM)— aro
Bicozamycinum (EXACT_SYNONYM)— aro

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.

antibacterial agent CHEBI:33282

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
ARO	`ARO:0000055`	bicyclomycin	`antibioticmech:aro-b86b27b1dd`	2026-08-30
CHEBI	`CHEBI:60584`	bicozamycin	`antibioticmech:chebi-b84bb7c116`	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.

rho transcription terminator factor PROTEIN DIRECT_BINDING_TARGET

ARO:3000736

CARD/ARO database assertion; target organism, strain, and assay are not specified. Rho termination factor is asserted as the antibiotic target. Evidence status: PRIMARY_EVIDENCE_NEEDED. Source: CARD_ARO 2026-08-30 (retrieved 2026-08-30).

ARO:3000736 (CARD/ARO asserts targeted_by_antibiotic ARO:0000055 (bicyclomycin); database assertion, not a primary citation.)

Rho transcription termination factor PROTEIN_COMPLEX DIRECT_BINDING_TARGET

A 3.15-angstrom Rho-bicyclomycin crystal structure directly localized the drug next to ATP- and RNA-binding sites and showed occlusion of the water required for ATP hydrolysis. Evidence status: PRIMARY_EVIDENCE. Source: PRIMARY_LITERATURE 2005-01 (retrieved 2026-09-02).

Escherichia coli NCBITaxon:562

Organism-specific examples
Protein	Gene	Organism	Entry
Transcription termination factor Rho `UniProtKB:P0AG30` Reviewed Rho reference (UniProt entry 164, sequence 1), mapped by PDB 1XPO entity 2. One Rho subunit, not the whole complex or a resistance allele. K-12 is the UniProt reference scope, not an assigned experimental strain; PDB reports the source species as Escherichia coli (NCBITaxon:562).	rho	Escherichia coli (strain K12) `NCBITaxon:83333`	REVIEWED

PMID:15642265 (Primary bicyclomycin-bound Rho structural mechanism study (DOI:10.1016/j.str.2004.10.013).)
PDB:1XPO (Reference crosswalk checked 2026-10-13: PDB entry 1.4 (2024-12-25), entity 2 maps to UniProtKB:P0AG30 and source species NCBITaxon:562. BCM has exact Standard InChIKey WOUDXEYYJPOSNE-VKZDFBPFSA-N. PDB and UniProt cite PMID:15642265; this supplements the existing primary cocrystal claim, not a new resistance or MIC assertion. https://www.rcsb.org/structure/1XPO K-12 is reference context, not an assigned experimental strain; P0AG30 identifies one subunit, not the whole complex.)

Mechanism summary

Mode of action: NUCLEIC_ACID_SYNTHESIS_INHIBITION microbial target — CURATOR: Bicozamycin and bicyclomycin are exact synonyms on the merged ChEBI/CARD record. PMID:15642265 resolved bicyclomycin in bacterial Rho, where it binds beside the ATP- and RNA-binding sites and noncompetitively blocks ATP turnover by excluding the nucleophilic water needed for hydrolysis, thereby disrupting Rho-dependent transcription termination.

Resistance mechanisms

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

ANTIBIOTIC_EFFLUX 1

ANTIBIOTIC_EFFLUX
Determinant	ARO ID	Organism	Gene families	Evidence
bcr-1	ARO:3003801	not organism-specific	—	ARO:3003801 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000055 (bicyclomycin); database assertion, not a primary citation.)

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.

Producer organisms
Organism	BGC	Cluster link evidence	Source	Quality	Note	Evidence
Streptomyces cinnamoneus NCBITaxon:53446	BGC0001468	Enzymatic assays; Heterologous expression compound specific	MIBIG 4.0.1 (entry 5)	questionable	MIBiG active entry; compound 'bicyclomycin' joined by exact Standard InChIKey.	PMID:29053243 (MIBiG's first legacy reference for the entry, inherited rather than attached to the compound. It supports that the entry exists; it is NOT established as evidence for this specific producer/compound link.)

Record-level evidence

PMID:15642265 (Primary exact-bicyclomycin/bicozamycin Rho cocrystal and ATPase-mechanism study.)

Curation history

SEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Seeded from data/raw/ inventories (ARO, 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 2026-08-31 · seed_from_sources
Re-seeded from updated data/raw/ inventories
REVIEWED 2026-09-03 · codex · LLM-assisted
Verified the exact bicozamycin/bicyclomycin synonym identity, ChEBI/CARD structure, antibacterial role, class, and retained CARD assertions; added transcription-termination inhibition and the directly bound Rho complex.
RESEEDED_FROM_SOURCES 2026-09-08 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-09-08 · seed_from_sources
Re-seeded from updated data/raw/ inventories
REGROUNDED 2026-10-13 · codex · LLM-assisted
Added a versioned Rho protein example and source-species context to the literature-owned bicyclomycin target through the exact-ligand PDB 1XPO/UniProt crosswalk. Preserved all CARD and MIBiG assertions; no resistance allele, genome, or numerical AST assignment.

Provenance

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

Explore across X-Mech: MediaIngredientMech (bicozamycin) · CultureMech · NaturalProductMech · PathwayMech · TraitMech · TaxonMech (Streptomyces cinnamoneus)