thiolutin

CHEBI:156450 ·resolve ·ANTIBACTERIAL ·EXACT SEEDED

A dithiolopyrrolone antibiotic that is 4,5-dihydro[1,2]dithiolo[4,3-b]pyrrole in which the hydrogens at positions 4,5 and 6 have been replaced by methyl, oxo and acetamido groups, respectively. It is a potent inhibitor of RNA polymerases, inhibits the angiogenesis of human umbilical vein endothelial cells, and also inhibits JAMM metalloproteases. — 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

Strictly broader compounds or drug classes this molecule belongs to.

CHEBI:156449 CHEBI:156449
CHEBI:22160 CHEBI:22160

Chemical structure

Computed structure properties
Molecular formula	C8H8N2O2S2
Charge	0
Average mass	228.298 Da
Monoisotopic mass	228.00272 Da
Source	ChEBI
InChIKey	MHMRAFONCSQAIA-UHFFFAOYSA-N

SMILES

CC(=O)Nc1c2sscc-2n(C)c1=O

InChI

InChI=1S/C8H8N2O2S2/c1-4(11)9-6-7-5(3-13-14-7)10(2)8(6)12/h3H,1-2H3,(H,9,11)

Also called

N-(4-methyl-5-oxo-4,5-dihydro[1,2]dithiolo[4,3-b]pyrrol-6-yl)acetamide (EXACT_SYNONYM)— chebi
6-acetamido-4-methyl-1,2-dithiolo[4,3-b]pyrrol-5(4H)-one (EXACT_SYNONYM)— chebi
N-(4,5-dihydro-4-methyl-5-oxo-1,2-dithiolo[4,3-b]pyrrol-6-yl)acetamide (EXACT_SYNONYM)— chebi
N-(4-methyl-5-oxodithiolo[4,3-b]pyrrol-6-yl)acetamide (EXACT_SYNONYM)— chebi
acetopyrrothin (EXACT_SYNONYM)— chebi
acetopyrrothine (EXACT_SYNONYM)— chebi

Cross-references

Equivalent identifiers for this same structure in other resources.

cas:87-11-6
foodb.food:FDB012539
hmdb:HMDB0034228
metacyc.compound:CPD-17934
reaxys:209485
wikipedia.en:Thiolutin

Activity roles

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

CHEBI:33281 CHEBI:33281
CHEBI:33282 CHEBI:33282
CHEBI:35718 CHEBI:35718

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:156450`	thiolutin	`antibioticmech:chebi-4e6261f444`	2026-08-30

Mechanism summary

Mode of action: MULTIPLE host shared target — Assigned from ChEBI roles CHEBI:37416 (EC 2.7.7.6 (RNA polymerase) inhibitor), CHEBI:48001 (protein synthesis inhibitor), which map to NUCLEIC_ACID_SYNTHESIS_INHIBITION, PROTEIN_SYNTHESIS_INHIBITION. ChEBI asserts these roles on the compound; a curator should decide whether one is primary. 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.

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

Provenance

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