althiomycin

CHEBI:157683 ·resolve ·ANTIBACTERIAL ·EXACT REVIEWED

A peptide antibiotic isolated from soil and enteric bacteria. It is a protein synthesis inhibitor which exhibits antibacterial activity against both Gram-positive and Gram-negative bacteria. — ChEBI

Classification

Strictly broader compounds or drug classes this molecule belongs to.

Label unavailable CHEBI:140325
Label unavailable CHEBI:140326
Label unavailable CHEBI:15734
Label unavailable CHEBI:22307
Label unavailable CHEBI:23763
Label unavailable CHEBI:25698
peptide antibiotic CHEBI:25903
Label unavailable CHEBI:38418
Label unavailable CHEBI:74222

Chemical structure

Computed structure properties
Molecular formula	C16H17N5O6S2
Charge	0
Average mass	439.475 Da
Monoisotopic mass	439.06203 Da
Source	ChEBI
InChIKey	VQQNQKXWJMRPHT-GMLCBOFYSA-N

SMILES

COC1=CC(=O)N(C(=O)[C@H]2CSC(C(CO)NC(=O)c3csc(/C=N/O)n3)=N2)C1

InChI

InChI=1S/C16H17N5O6S2/c1-27-8-2-13(23)21(4-8)16(25)11-7-29-15(20-11)9(5-22)19-14(24)10-6-28-12(18-10)3-17-26/h2-3,6,9,11,22,26H,4-5,7H2,1H3,(H,19,24)/b17-3+/t9?,11-/m1/s1

Also called

2-[(E)-(hydroxyimino)methyl]-N-(2-hydroxy-1-{(4S)-4-[(4-methoxy-2-oxo-2,5-dihydro-1H-pyrrol-1-yl)carbonyl]-4,5-dihydro-1,3-thiazol-2-yl}ethyl)-1,3-thiazole-4-carboxamide (EXACT_SYNONYM)— chebi
116-A (EXACT_SYNONYM)— chebi
N-{2-hydroxy-1-[(4S)-4-(4-methoxy-2-oxo-2,5-dihydro-1H-pyrrole-1-carbonyl)-4,5-dihydro-1,3-thiazol-2-yl]ethyl}-2-[(E)-(hydroxyimino)methyl]-1,3-thiazole-4-carboxamide (EXACT_SYNONYM)— chebi
altiomycin (EXACT_SYNONYM)— chebi
matamycin (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.

Patents and articles

Documents about this compound. A patent covers a class and an article covers a topic; neither identifies a structure.

wikipedia.en:Althiomycin

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

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:157683`	althiomycin	`antibioticmech:chebi-8564797afb`	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.

bacterial ribosomal peptidyl-transferase reaction BIOLOGICAL_PROCESS MEASURED_TARGET_ASSOCIATION

Intact-cell and cell-free protein-synthesis assays; the puromycin reaction was inhibited while aminoacyl-tRNA synthesis and aminoacyl-tRNA binding to ribosomes were not. Evidence status: PRIMARY_EVIDENCE. Source: PRIMARY_LITERATURE 1970-06 (retrieved 2026-09-02).

Escherichia coli NCBITaxon:562; strain B

PMID:4917791 — "In the cell-free system althiomycin was confirmed to inhibit protein synthesis." (Compound-specific experimental study; supports a ribosomal translation effect, not a direct-binding claim.)

Mechanism summary

Mode of action: PROTEIN_SYNTHESIS_INHIBITION microbial target — CURATOR: Confirmed against PMID:4917791 in intact-cell and cell-free Escherichia coli B assays. Althiomycin inhibited bacterial protein synthesis and the puromycin reaction without inhibiting aminoacyl-tRNA synthesis or aminoacyl-tRNA binding to ribosomes. The microbial scope replaces the generic role-derived HOST_SHARED_TARGET value.

Activity spectrum

Measured or curated activity against specific taxa. A number without a method is not an observation — every row here carries an assay.

2 observations · Browse all observations · Complete record (JSON.gz)

Activity observations
Organism	Activity	MIC	Disk diffusion	Assay	Strain	Sample/genome	Evidence
Bacillus subtilis NCBITaxon:1423	ACTIVE	—	—	Growth inhibition by the diffusible product of Serratia marcescens Db10; althiomycin identity confirmed by chromatographic and spectroscopic analysis.	—	—	Evidence Page data (JSON.gz)
Staphylococcus aureus NCBITaxon:1280	ACTIVE	—	—	Growth inhibition by the diffusible product of Serratia marcescens Db10; althiomycin identity confirmed by chromatographic and spectroscopic analysis.	—	—	Evidence Page data (JSON.gz)

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
Myxococcus xanthus NCBITaxon:34 strain DK897	BGC0000955	—	PRIMARY_LITERATURE_AND_MIBIG	—	The althiomycin NRPS-PKS cluster was identified by gene inactivation; MIBiG BGC0000955 links the characterized cluster.	PMID:21626639 (Primary biosynthetic-gene-cluster study in Myxococcus xanthus DK897.)
Serratia marcescens NCBITaxon:615 strain Db10	—	—	PRIMARY_LITERATURE	—	Chromatographic and spectroscopic analysis identified althiomycin, and disruption of the alb cluster eliminated production.	PMID:23028578 (Primary producer, biosynthesis, and activity study in Serratia marcescens Db10.)

Record-level evidence

PMID:13513511 (Primary discovery, production, and antibacterial-activity report.)
PMID:1150528 (Primary chemical-structure determination.)
PMID:4917791 (Primary experimental mode-of-action study.)
PMID:21626639 (Primary biosynthetic-gene-cluster study in Myxococcus xanthus DK897.)
PMID:23028578 (Primary producer, biosynthesis, and activity study in Serratia marcescens Db10.)

Curation history

SEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Seeded from data/raw/ inventories (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
REVIEWED 2026-09-02 · codex · LLM-assisted
Verified ChEBI identity and structure; confirmed protein-synthesis mechanism and corrected target scope with PMID:4917791; added a primary-evidence molecular process target, two producer assertions, two qualitative activity observations, and record-level evidence.
RESEEDED_FROM_SOURCES 2026-09-10 · 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).

Explore across X-Mech: MediaIngredientMech (althiomycin) · CultureMech · NaturalProductMech · PathwayMech · TraitMech · TaxonMech (Myxococcus xanthus)