tetracenomycin X

CHEBI:32209 ·resolve ·ANTIBACTERIAL ·EXACT REVIEWED

Tetracenomycin X is a tetracenomycin antibiotic, a methyl ester and a tertiary alpha-hydroxy ketone. — PMID:32601485

Classification

tetracenomycin antibioticARO:3007034

Strictly broader compounds or drug classes this molecule belongs to.

Label unavailable CHEBI:139592
Label unavailable CHEBI:25248
tetracenomycin CHEBI:48132
tetracenomycin antibiotic ARO:3007034

Chemical structure

Computed structure properties
Molecular formula	C24H20O11
Charge	0
Average mass	484.413 Da
Monoisotopic mass	484.10056 Da
Source	ChEBI
InChIKey	CCDBRFCICQZPPE-DNQXCXABSA-N

SMILES

COC(=O)c1c(OC)cc2cc3c(c(O)c2c1C)C(=O)[C@]1(OC)C(=O)C=C(OC)C(=O)[C@]1(O)C3=O

InChI

InChI=1S/C24H20O11/c1-9-15-10(7-12(32-2)16(9)22(30)34-4)6-11-17(18(15)26)21(29)24(35-5)14(25)8-13(33-3)20(28)23(24,31)19(11)27/h6-8,26,31H,1-5H3/t23-,24-/m1/s1

Also called

methyl (6aR,10aR)-6a,12-dihydroxy-3,8,10a-trimethoxy-1-methyl-6,7,10,11-tetraoxo-6,6a,7,10,10a,11-hexahydrotetracene-2-carboxylate (EXACT_SYNONYM)— chebi
Tetracenomycin X (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.

Activity roles

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

antimicrobial agent CHEBI:33281

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:3007036`	tetracenomycin X	`antibioticmech:aro-78e3eb33d0`	2026-08-30
CHEBI	`CHEBI:32209`	tetracenomycin X	`antibioticmech:chebi-dedb4de9ba`	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.

polypeptide exit tunnel of the bacterial 50S ribosomal subunit RIBOSOMAL_SUBUNIT DIRECT_BINDING_TARGET

Compound-specific translation assays and structural analysis localized binding beside the macrolide site, at the 23S rRNA U1782-U2586 noncanonical base pair. The abstract does not state the structural model organism, so no taxon is asserted. Evidence status: PRIMARY_EVIDENCE. Source: PRIMARY_LITERATURE 2020-10 (retrieved 2026-09-02).

PMID:32601485 (Primary compound-specific biochemical and structural study; distinguishes the large-subunit exit-tunnel target from the small subunit and from DNA damage.)

Mechanism summary

Mode of action: PROTEIN_SYNTHESIS_INHIBITION host shared target — CURATOR: PMID:32601485 showed that tetracenomycin X binds in the polypeptide exit tunnel of the bacterial large ribosomal subunit and blocks translation after short oligopeptides are made. The same study reported that the compound does not induce DNA damage, correcting the previously proposed mechanism.

Record-level evidence

PMID:32601485 (Primary experimental mechanism, target, and structure 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
REVIEWED 2026-09-02 · codex · LLM-assisted
Verified identity, structure, and antibacterial class; added the primary-evidence bacterial 50S exit-tunnel target and corrected the mechanism from the historical DNA-damage proposal to translation inhibition.

Provenance

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

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