thiostrepton

CHEBI:29693 ·resolve ·ANTIBACTERIAL ·EXACT REVIEWED

A heterodetic cyclic peptide, in which the cyclisation step involves a formal lactonisation between the carboxy group of a quinaldic acid-based residue and a secondary alcohol. An antibiotic that inhibits bacterial protein synthesis. Also acts as an antitumor agent. — ChEBI

Classification

ribosomally synthesized and post-translationally modified peptide antibioticsARO:3009656

Strictly broader compounds or drug classes this molecule belongs to.

Label unavailable CHEBI:24533
ribosomally synthesized and post-translationally modified peptide antibiotics ARO:3009656

Chemical structure

Computed structure properties
Molecular formula	C72H85N19O18S5
Charge	0
Average mass	1664.922 Da
Monoisotopic mass	1663.49235 Da
Source	ChEBI
InChIKey	NSFFHOGKXHRQEW-AIHSUZKVSA-N

SMILES

[H][C@]12N=C(c3nc(C(=O)NC(=C)C(=O)NC(=C)C(N)=O)cs3)CC[C@@]13NC(=O)[C@H](C)NC(=O)C(=C)NC(=O)[C@H](C)NC(=O)[C@H]([C@@H](C)CC)N[C@@H]1C=Cc4c([C@H](C)O)cc(nc4[C@H]1O)C(=O)O[C@H](C)[C@H](NC(=O)c1csc(n1)[C@H]([C@](C)(O)[C@@H](C)O)NC(=O)[C@H]1CSC(=N1)/C(=C/C)NC(=O)[C@H]([C@@H](C)O)NC(=O)c1csc3n1)c1nc2cs1

InChI

InChI=1S/C72H85N19O18S5/c1-14-26(3)47-63(105)78-30(7)57(99)75-28(5)56(98)76-31(8)58(100)91-72-19-18-40(66-85-43(22-111-66)59(101)77-29(6)55(97)74-27(4)54(73)96)81-52(72)42-21-112-67(83-42)49(34(11)109-69(107)41-20-37(32(9)92)36-16-17-39(79-47)51(95)50(36)80-41)89-60(102)44-24-113-68(86-44)53(71(13,108)35(12)94)90-62(104)45-23-110-65(84-45)38(15-2)82-64(106)48(33(10)93)88-61(103)46-25-114-70(72)87-46/h15-17,20-22,24-26,30-35,39,45,47-49,51-53,79,92-95,108H,4-6,14,18-19,23H2,1-3,7-13H3,(H2,73,96)(H,74,97)(H,75,99)(H,76,98)(H,77,101)(H,78,105)(H,82,106)(H,88,103)(H,89,102)(H,90,104)(H,91,100)/b38-15-/t26-,30-,31-,32-,33+,34+,35+,39+,45+,47-,48-,49-,51-,52+,53+,71+,72+/m0/s1

Also called

Thiostrepton (EXACT_SYNONYM)— chebi
bryamycin (EXACT_SYNONYM)— chebi
gargon (EXACT_SYNONYM)— chebi
thiactin (EXACT_SYNONYM)— chebi
thiostrepton A (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.

Drug registries

Identifiers that name a drug rather than a structure. One of these can cover a parent compound, its salts and its stereoisomers, which this corpus keeps as separate records, so it is not an equivalence of structure.

Patents and articles

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

wikipedia.en:Thiostrepton

Activity roles

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

antibacterial drug CHEBI:36047

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:3000686`	thiostrepton	`antibioticmech:aro-a8c48c531c`	2026-08-30
CHEBI	`CHEBI:29693`	thiostrepton	`antibioticmech:chebi-c0376c1060`	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.

50S ribosomal subunit P-site RIBOSOMAL_SUBUNIT DIRECT_BINDING_TARGET

ARO:3000757

CARD/ARO database assertion; target organism, strain, and assay are not specified. The 50S P-site is asserted as the target site. Evidence status: PRIMARY_EVIDENCE_NEEDED. Source: CARD_ARO 2026-08-30 (retrieved 2026-08-30).

ARO:3000757 (CARD/ARO asserts targeted_by_antibiotic ARO:3000686 (thiostrepton); database assertion, not a primary citation.)

70S ribosome GTPase-associated center RIBOSOMAL_SUBUNIT MEASURED_TARGET_ASSOCIATION

70S binding and GTP-hydrolysis assays showed loss of stable EF-G and EF4 engagement at 0.15 micromolar thiostrepton; no compound-bound structure was reported in this study. Evidence status: PRIMARY_EVIDENCE. Source: PRIMARY_LITERATURE 2011-09 (retrieved 2026-09-02).

PMID:21908407 (Primary 70S-factor binding, GTPase, truncation, and footprinting study (DOI:10.1093/nar/gkr623).)

Mechanism summary

Mode of action: PROTEIN_SYNTHESIS_INHIBITION host shared target — CURATOR: PMID:21908407 measured thiostrepton inhibition of stable 70S binding and ribosome-dependent GTP hydrolysis for elongation factors EF-G and EF4. A truncated EF-G lacking domains IV and V remained active and thiostrepton-insensitive, supporting disruption of factor-ribosome engagement rather than direct inhibition of the soluble factors.

Resistance mechanisms

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

ANTIBIOTIC_TARGET_ALTERATION 1

ANTIBIOTIC_TARGET_ALTERATION
Determinant	ARO ID	Organism	Gene families	Evidence
tsnR	ARO:3003060	not organism-specific	—	ARO:3003060 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000686 (thiostrepton); database assertion, not a primary citation.)

Record-level evidence

PMID:21908407 (Primary thiostrepton 70S-factor binding and GTPase 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 2026-09-02 · codex · LLM-assisted
Verified exact ChEBI/CARD identity, structure, roles, class, and retained CARD target/resistance provenance; curator-confirmed protein-synthesis inhibition and added the measured ribosomal GTPase-center association.
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).

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