thiostrepton

CHEBI:29693 ·resolve ·ANTIBACTERIAL ·EXACT SEEDED

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

Machine-generated and unreviewed. Identity, structure and cross-references come straight from ChEBI's and CARD's own data; no curator has signed off on this record yet.

Classification

ribosomally synthesized and post-translationally modified peptide antibioticsARO:3009656

Strictly broader compounds or drug classes this molecule belongs to.

CHEBI:24533 CHEBI:24533
ARO:3009656 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

Equivalent identifiers for this same structure in other resources.

ARO:3000686
cas:1393-48-2
drugbank:DB11467
kegg.compound:C12054
kegg.drug:D06111
knapsack:C00000753
metacyc.compound:CPD-13481
reaxys:7390758
vsdb:3007
wikipedia.en:Thiostrepton
chembl:CHEMBL1236460
pubchem.compound:16129666

Activity roles

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

CHEBI:36047 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.)

Mechanism summary

Mode of action: PROTEIN_SYNTHESIS_INHIBITION host shared target — Assigned from ChEBI role CHEBI:48001 (protein synthesis inhibitor). ChEBI asserts the role on the compound. The target it names is one the host has too, so the mechanism is true but is not evidence of selectivity — see mode_of_action_target_scope. Not a curator's mechanistic review.

Resistance mechanisms

1 known routes by which microbes resist this compound, grounded in ARO where CARD models them. Grouped by mechanism type — expand a group to see its determinants.

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.)

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

Provenance

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