tropodithietic acid
CHEBI:156455 EXACT SEEDED antibacterialcytotoxic
A monocarboxylic acid that is 8,9-dithiabicyclo[5.2.0]nona-1,3,6-triene substituted by a carboxy group at position 2 and an oxo group at position 3. It is a broad spectrum antibiotic produced by the marine bacterium Phaeobacter inhibens that also acts as a signalling molecule at lower concentrations.
Structure
| Standard InChIKey | BLFCMITWMARUSM-UHFFFAOYSA-N |
|---|---|
| SMILES | C1=CC(=O)C(=C2C(=C1)SS2)C(=O)O |
| Stereochemistry | fully defined |
| Cross-references | pubchem:44632924 |
Filing pathway
Shikimates and phenylpropanoids — 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 other, 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 |
|---|---|---|---|
| Phaeobacter inhibens DSM 17395 NCBITaxon:391619 |
SOURCE_ASSERTION | mibig:BGC0000932 | PMID:24723119 |
Occurrences 6
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 |
|---|---|---|
| Phaeobacter inhibens NCBITaxon:221822 |
LOTUS | DOI:10.1039/C4CC01924E |
| Phaeobacter inhibens NCBITaxon:221822 |
LOTUS | DOI:10.1128/MBIO.02118-15 |
| Phaeobacter inhibens NCBITaxon:221822 |
CHEBI | PMID:28389641 |
| Roseobacter NCBITaxon:2433 |
LOTUS | DOI:10.1128/AEM.70.4.2560-2565.2003 |
| Phaeobacter gallaeciensis NCBITaxon:60890 |
CHEBI | PMID:21430694 |
| Phaeobacter inhibens DSM 17395 NCBITaxon:391619 |
CHEBI | PMID:25161739 |
Biosynthetic gene clusters 1
| Accession | Host | Locus evidence | Genome |
|---|---|---|---|
| mibig:BGC0000932 | Phaeobacter inhibens DSM 17395 NCBITaxon:391619 |
CLUSTER_UNSTATED | genbank:CP002977.1 |
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 |
|---|---|---|
| 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 |
| NCI human tumor cell line growth inhibition assay. Data for the ACHN Non-Small Cell Lung cell line, single concentration | ACTIVE | pubchem.aid:1794771 |
| NCI human tumor cell line growth inhibition assay. Data for the CCRF-CEM Non-Small Cell Lung cell line, single concentration | ACTIVE | pubchem.aid:1794778 |
| NCI human tumor cell line growth inhibition assay. Data for the COLO 205 Non-Small Cell Lung cell line, single concentration | ACTIVE | pubchem.aid:1794742 |
| NCI human tumor cell line growth inhibition assay. Data for the DU-145 Non-Small Cell Lung cell line, single concentration | ACTIVE | pubchem.aid:1794760 |
| NCI human tumor cell line growth inhibition assay. Data for the HCT-116 Non-Small Cell Lung cell line, single concentration | ACTIVE | pubchem.aid:1794798 |
| NCI human tumor cell line growth inhibition assay. Data for the HCT-15 Non-Small Cell Lung cell line, single concentration | ACTIVE | pubchem.aid:1794746 |
| NCI human tumor cell line growth inhibition assay. Data for the HL-60(TB) Non-Small Cell Lung cell line, single concentration | ACTIVE | pubchem.aid:1794776 |
| NCI human tumor cell line growth inhibition assay. Data for the HOP-62 Non-Small Cell Lung cell line, single concentration | ACTIVE | pubchem.aid:1794735 |
| NCI human tumor cell line growth inhibition assay. Data for the HOP-92 Non-Small Cell Lung cell line, single concentration | ACTIVE | pubchem.aid:1794738 |
| NCI human tumor cell line growth inhibition assay. Data for the HT29 Non-Small Cell Lung cell line, single concentration | ACTIVE | pubchem.aid:1794748 |
| NCI human tumor cell line growth inhibition assay. Data for the K-562 Non-Small Cell Lung cell line, single concentration | ACTIVE | pubchem.aid:1794777 |
| NCI human tumor cell line growth inhibition assay. Data for the KM12 Non-Small Cell Lung cell line, single concentration | ACTIVE | pubchem.aid:1794800 |
| NCI human tumor cell line growth inhibition assay. Data for the LOX IMVI Non-Small Cell Lung cell line, single concentration | ACTIVE | pubchem.aid:1794757 |
| NCI human tumor cell line growth inhibition assay. Data for the M14 Non-Small Cell Lung cell line, single concentration | ACTIVE | pubchem.aid:1794745 |
| NCI human tumor cell line growth inhibition assay. Data for the MALME-3M Non-Small Cell Lung cell line, single concentration | ACTIVE | pubchem.aid:1794766 |
| NCI human tumor cell line growth inhibition assay. Data for the MCF7 Non-Small Cell Lung cell line, single concentration | ACTIVE | pubchem.aid:1794796 |
| NCI human tumor cell line growth inhibition assay. Data for the MDA-MB-231/ATCC Non-Small Cell Lung cell line, single concentration | ACTIVE | pubchem.aid:1794789 |
| NCI human tumor cell line growth inhibition assay. Data for the MDA-MB-468 Breast cell line, single concentration | ACTIVE | pubchem.aid:2202374 |
| NCI human tumor cell line growth inhibition assay. Data for the MOLT-4 Non-Small Cell Lung cell line, single concentration | ACTIVE | pubchem.aid:1794779 |
| NCI human tumor cell line growth inhibition assay. Data for the NCI-H226 Non-Small Cell Lung cell line, single concentration | ACTIVE | pubchem.aid:1794732 |
| NCI human tumor cell line growth inhibition assay. Data for the NCI-H23 Non-Small Cell Lung cell line, single concentration | ACTIVE | pubchem.aid:1794731 |
| NCI human tumor cell line growth inhibition assay. Data for the NCI-H460 Non-Small Cell Lung cell line, single concentration | ACTIVE | pubchem.aid:1794736 |
Elsewhere in the fleet
- AntibioticMech — CHEBI:156455 (same structure, same inchikey)
Provenance
| Source concept | Source | Version |
|---|---|---|
| BGC0000932 | MIBIG | 5 |
| CHEBI:156455 | CHEBI | 3-star |
This page is generated from data/natural_products/shikimates_and_phenylpropanoids/tropodithietic-acid.yaml, which is generated from the committed inventories. Neither is edited by hand.