thiolutin
CHEBI:156450 EXACT SEEDED antibacterialcytotoxicenzyme inhibitor
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antibiotic that is 4,5-dihydro[1,2]dithiolo[4,3-b]pyrrole in which the hydrogens at positions 4,5 and 6 have been replaced by methyl, oxo and acetamido groups, respectively.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.
Structure
| Standard InChIKey | MHMRAFONCSQAIA-UHFFFAOYSA-N |
|---|---|
| SMILES | CN1C(=O)C(NC(C)=O)=C2SSC=C12 |
| Stereochemistry | fully defined |
| Cross-references | npatlas:NPA05113, pubchem:6870 |
Filing pathway
Alkaloids — computed by NPClassifier npclassifier.gnps2.org@2026-09-07, which is why it is pinned rather than recomputed. The gene cluster's asserted class is nrps, from MIBiG.
Producer organisms 1
A claim that this taxon makes the compound. The basis says what the evidence addressed — a knockout and a database assertion are not the same claim.
| Taxon | Basis | Cluster | Evidence |
|---|---|---|---|
| Saccharothrix algeriensis NCBITaxon:173560 |
SOURCE_ASSERTION | mibig:BGC0001193 | PMID:25353334 |
Occurrences 5
Somebody found the compound in this organism and cited it. That is not a claim that the organism makes it, and nothing here promotes one to the other.
| Taxon | Source | Reference |
|---|---|---|
| Streptomyces kasugaensis NCBITaxon:1946 |
LOTUS | DOI:10.1007/BF02821279 |
| Streptomyces kasugaensis NCBITaxon:1946 |
CHEBI | PMID:2262169 |
| Streptomyces celluloflavus NCBITaxon:58344 |
LOTUS | DOI:10.1007/BF02821279 |
| Saccharothrix algeriensis NCBITaxon:173560 |
LOTUS | DOI:10.2174/1871520614666141027145200 |
| Saccharothrix algeriensis NCBITaxon:173560 |
CHEBI | PMID:24723205 |
Biosynthetic gene clusters 1
| Accession | Host | Locus evidence | Genome |
|---|---|---|---|
| mibig:BGC0001193 | Saccharothrix algeriensis NCBITaxon:173560 |
CLUSTER_UNSTATED | genbank:KM114209.1 |
A locus claim and a taxon claim are different questions. Heterologous expression settles the first and leaves the second where the isolation report left it.
Bioactivities 25
| Assay | Result | Reference |
|---|---|---|
| Inhibitors of the vitamin D receptor (VDR): qHTS | 39.8107 uM | pubchem.aid:504847 |
| VP16 counterscreen qHTS for inhibitors of ROR gamma transcriptional activity | 0.2512 uM | pubchem.aid:2546 |
| qHTS Assay for Compounds Blocking the Interaction Between CBF-beta and RUNX1 for the Treatment of Acute Myeloid Leukemia | 17.7828 uM | pubchem.aid:1477 |
| qHTS Assay for Compounds that Induce Erasure of Genomic Imprints | 0.7079 uM | pubchem.aid:1948 |
| qHTS Assay for Inhibitors of Bacillus subtilis Sfp phosphopantetheinyl transferase (PPTase) | 17.7828 uM | pubchem.aid:1490 |
| qHTS Assay for Inhibitors of the Human Apurinic/apyrimidinic Endonuclease 1 (APE1) | 0.005 uM | pubchem.aid:2517 |
| qHTS for Inhibitors of Tau Fibril Formation, Fluorescence Polarization | 17.7828 uM | pubchem.aid:1468 |
| qHTS for Inhibitors of Tau Fibril Formation, Thioflavin T Binding | 15.8489 uM | pubchem.aid:1460 |
| qHTS for Inhibitors of binding or entry into cells for Lassa Virus | 10 uM | pubchem.aid:720533 |
| qHTS for Inhibitors of binding or entry into cells for Marburg Virus | 11.2202 uM | pubchem.aid:720532 |
| qHTS for inhibitors of ROR gamma transcriptional activity | 0.3981 uM | pubchem.aid:2551 |
| A qHTS for Small Molecule Inhibitors of Shiga Toxin | ACTIVE | pubchem.aid:2315 |
| A qHTS for Small Molecule Inhibitors of Shiga Toxin | ACTIVE | pubchem.aid:2315 |
| Cycloheximide Counterscreen for Small Molecule Inhibitors of Shiga Toxin | ACTIVE | pubchem.aid:2314 |
| Cycloheximide Counterscreen for Small Molecule Inhibitors of Shiga Toxin | ACTIVE | pubchem.aid:2314 |
| NCATS Parallel Artificial Membrane Permeability Assay (PAMPA) - Blood-Brain Barrier (BBB) Permeability Screen | ACTIVE | PMID:38108064 |
| NCI Yeast Anticancer Drug Screen. Data for the bub3 strain | ACTIVE | pubchem.aid:167 |
| NCI Yeast Anticancer Drug Screen. Data for the cln2 rad14 strain | ACTIVE | pubchem.aid:165 |
| NCI Yeast Anticancer Drug Screen. Data for the mec2-1 strain | ACTIVE | pubchem.aid:157 |
| NCI Yeast Anticancer Drug Screen. Data for the mlh1 rad18 strain | ACTIVE | pubchem.aid:175 |
| NCI Yeast Anticancer Drug Screen. Data for the rad50 strain | ACTIVE | pubchem.aid:155 |
| NCI Yeast Anticancer Drug Screen. Data for the sgs1 mgt1 strain | ACTIVE | pubchem.aid:161 |
| NCI human tumor cell line growth inhibition assay. Data for the 786-0 Non-Small Cell Lung cell line, single concentration | ACTIVE | pubchem.aid:1794775 |
| NCI human tumor cell line growth inhibition assay. Data for the A498 Non-Small Cell Lung cell line, single concentration | ACTIVE | pubchem.aid:1794774 |
| NCI human tumor cell line growth inhibition assay. Data for the A549/ATCC Non-Small Cell Lung cell line, single concentration | ACTIVE | pubchem.aid:1794740 |
Elsewhere in the fleet
- AntibioticMech — CHEBI:156450 (same structure, same inchikey)
Provenance
| Source concept | Source | Version |
|---|---|---|
| BGC0001193 | MIBIG | 5 |
| CHEBI:156450 | CHEBI | 3-star |
This page is generated from data/natural_products/alkaloids/thiolutin.yaml, which is generated from the committed inventories. Neither is edited by hand.