pederin
CHEBI:78591 EXACT SEEDED cytotoxic
A polyketide and carboxamide produced by a (Pseudomonas) bacterial endosymbiont of certain rove beetles (genus Paederus). Pederin is the agent responsible for the vesicant effects (linear or Paederus dermatitis) when the beetle is crushed against the skin. It is a powerful inhibitor of protein biosynthesis and mitosis and a potent antitumour agent.
Structure
| Standard InChIKey | ZNEZZONMADKYTB-VRCUBXEUSA-N |
|---|---|
| SMILES | C[C@H]1[C@H](O[C@](CC1=C)([C@@H](C(=O)N[C@H]([C@@H]2C[C@H](C([C@H](O2)C[C@@H](COC)OC)(C)C)O)OC)O)OC)C |
| Stereochemistry | fully defined |
| Cross-references | pubchem:5381287, npatlas:NPA020381 |
Filing pathway
Polyketides — 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 pks, nrps, from MIBiG.
Producer organisms 0
None. The compound has a characterized gene cluster whose host NCBI does not name, which for an uncultured symbiont is the honest state — see the discussion below.
Occurrences 1
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 |
|---|---|---|
| Pseudomonas aeruginosa NCBITaxon:287 |
LOTUS | DOI:10.1128/JB.186.5.1280-1286.2004 |
Biosynthetic gene clusters 3
| Accession | Host | Locus evidence | Genome |
|---|---|---|---|
| mibig:BGC0000255 | not named | CLUSTER_UNSTATED | genbank:AY850690.1 |
| mibig:BGC0001108 | not named | CLUSTER_DEMONSTRATED | genbank:AY328023.1 |
| mibig:BGC0001109 | not named | CLUSTER_UNSTATED | genbank:DD161836.1 |
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 In Vivo Anticancer Drug Screen. Data for tumor model P388 Leukemia (intraperitoneal) in CD2F1 (CDF1) mice | ACTIVE | pubchem.aid:330 |
| 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 786-0 Renal cell line | ACTIVE | pubchem.aid:137 |
| 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 A498 Renal cell line | ACTIVE | pubchem.aid:129 |
| NCI human tumor cell line growth inhibition assay. Data for the A549/ATCC Non-Small Cell Lung cell line | ACTIVE | pubchem.aid:19 |
| 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 ACHN Renal cell line | ACTIVE | pubchem.aid:139 |
| NCI human tumor cell line growth inhibition assay. Data for the BT-549 Breast cell line | ACTIVE | pubchem.aid:89 |
| NCI human tumor cell line growth inhibition assay. Data for the BT-549 Non-Small Cell Lung cell line, single concentration | ACTIVE | pubchem.aid:1794793 |
| NCI human tumor cell line growth inhibition assay. Data for the CAKI-1 Non-Small Cell Lung cell line, single concentration | ACTIVE | pubchem.aid:1794772 |
| NCI human tumor cell line growth inhibition assay. Data for the CAKI-1 Renal cell line | ACTIVE | pubchem.aid:131 |
| NCI human tumor cell line growth inhibition assay. Data for the CCRF-CEM Leukemia cell line | ACTIVE | pubchem.aid:119 |
| 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 Colon cell line | ACTIVE | pubchem.aid:67 |
| 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 DU-145 Prostate cell line | ACTIVE | pubchem.aid:43 |
| NCI human tumor cell line growth inhibition assay. Data for the EKVX Non-Small Cell Lung cell line | ACTIVE | pubchem.aid:21 |
| NCI human tumor cell line growth inhibition assay. Data for the EKVX Non-Small Cell Lung cell line, single concentration | ACTIVE | pubchem.aid:1794765 |
| NCI human tumor cell line growth inhibition assay. Data for the HCC-2998 Colon cell line | ACTIVE | pubchem.aid:77 |
| NCI human tumor cell line growth inhibition assay. Data for the HCT-116 Colon cell line | ACTIVE | pubchem.aid:79 |
| 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 Colon cell line | ACTIVE | pubchem.aid:71 |
Open questions 2
shared-structure — This structure is reported by more than one MIBiG entry: BGC0000255, BGC0001108, BGC0001109. Confirm they describe the same compound rather than an upstream cross-reference error.
unnamed-producer — No producer claim is written from BGC0000255, which gives NCBITaxon:77133 (uncultured bacterium — shared by every unplaced bacterium); BGC0001108, which gives NCBITaxon:77133 (uncultured bacterium — shared by every unplaced bacterium); BGC0001109, which gives NCBITaxon:12908 (NCBI's bin for unclassified sequences), because the taxon names no single organism. The cluster is kept: a characterized locus is an origin assertion whether or not its host has a name, and for a compound from an uncultured symbiont that is the honest state. Name the producer if the primary literature does.
Provenance
| Source concept | Source | Version |
|---|---|---|
| BGC0000255 | MIBIG | 5 |
| BGC0001108 | MIBIG | 5 |
| BGC0001109 | MIBIG | 4 |
| CHEBI:78591 | CHEBI | 3-star |
This page is generated from data/natural_products/polyketides/pederin.yaml, which is generated from the committed inventories. Neither is edited by hand.