pyrrolnitrin
CHEBI:32079 EXACT SEEDED antifungalcytotoxicenzyme inhibitor
A member of the class of pyrroles carrying chloro and 3-chloro-2-nitrophenyl substituents at positions 3 and 4 respectively.
Structure
| Standard InChIKey | QJBZDBLBQWFTPZ-UHFFFAOYSA-N |
|---|---|
| SMILES | ClC1=CNC=C1C1=CC=CC(Cl)=C1N(=O)=O |
| Stereochemistry | fully defined |
| Cross-references | npatlas:NPA018752, pubchem:13916 |
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 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 |
|---|---|---|---|
| Pseudomonas chlororaphis NCBITaxon:587753 |
SOURCE_ASSERTION | mibig:BGC0000924 | PMID:19889032 |
Occurrences 18
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 phaeochromogenes NCBITaxon:1923 |
LOTUS | DOI:10.1016/0014-5793(84)81005-4 |
| Pseudomonas NCBITaxon:286 |
LOTUS | DOI:10.1080/00021369.1964.10858275 |
| Pseudomonas aeruginosa NCBITaxon:287 |
LOTUS | DOI:10.5507/BP.2012.090 |
| Burkholderia cepacia NCBITaxon:292 |
LOTUS | DOI:10.1016/S1049-9644(02)00044-0 |
| Burkholderia cepacia NCBITaxon:292 |
LOTUS | DOI:10.1021/JF00092A044 |
| Burkholderia cepacia NCBITaxon:292 |
LOTUS | DOI:10.1128/AEM.60.6.2031-2039.1994 |
| Acinetobacter haemolyticus NCBITaxon:29430 |
LOTUS | DOI:10.1007/S11274-013-1426-X |
| Acinetobacter haemolyticus NCBITaxon:29430 |
CHEBI | PMID:23990066 |
| Pseudomonas stutzeri NCBITaxon:316 |
LOTUS | DOI:10.5507/BP.2012.090 |
| Pseudomonas stutzeri NCBITaxon:316 |
CHEBI | PMID:23149469 |
| Pantoea agglomerans NCBITaxon:549 |
LOTUS | DOI:10.1007/S002849900037 |
| Burkholderia pyrrocinia NCBITaxon:60550 |
LOTUS | DOI:10.1002/ANIE.199403521 |
| Burkholderia pyrrocinia NCBITaxon:60550 |
CHEBI | PMID:4955234 |
| Pseudomonas chlororaphis NCBITaxon:587753 |
LOTUS | DOI:10.1094/MPMI-10-14-0326-FI |
| Pseudomonas chlororaphis NCBITaxon:587753 |
LOTUS | DOI:10.1111/J.1574-6941.2009.00792.X |
| Pseudomonas chlororaphis NCBITaxon:587753 |
LOTUS | DOI:10.1371/JOURNAL.PONE.0123184 |
| Pseudomonas chlororaphis NCBITaxon:587753 |
CHEBI | PMID:25679537 |
| Pseudomonas chlororaphis NCBITaxon:587753 |
CHEBI | PMID:25901993 |
Biosynthetic gene clusters 1
| Accession | Host | Locus evidence | Genome |
|---|---|---|---|
| mibig:BGC0000924 | Pseudomonas chlororaphis NCBITaxon:587753 |
CLUSTER_UNSTATED | genbank:EU188755.1 |
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 |
|---|---|---|
| A quantitative high throughput screen for small molecules that induce DNA re-replication in MCF 10a normal breast cells. | 21.136 uM | pubchem.aid:624296 |
| CYP3A4 induction through human pregnane X receptor (PXR) by small molecules, qHTS assay | 11.2202 uM | pubchem.aid:1346984 |
| Cytotoxicity counterscreen for inhibitors of SARS-CoV-2 cell entry | 39.8107 uM | pubchem.aid:1645845 |
| Human pregnane X receptor (PXR) activation by small molecules, qHTS assay | 14.1254 uM | pubchem.aid:1346985 |
| Inhibitors of USP1/UAF1: Pilot qHTS | 39.8107 uM | pubchem.aid:504865 |
| P-glycoprotein substrates identified in KB-8-5-11 adenocarcinoma cell line, qHTS therapeutic library screen | 29.0929 uM | PMID:31515284 |
| Primary qHTS assay for inhibitors of human arachidonate 12S-lipoxygenase (ALOX12): Round 2 | 100 uM | pubchem.aid:1671190 |
| Primary qHTS assay for inhibitors of human arachidonate 12S-lipoxygenase (ALOX12): Round 2 | 100 uM | pubchem.aid:1671190 |
| Primary qHTS for inhibitors of MERS-S pseudo-typed particle cell entry | 39.8107 uM | pubchem.aid:1479149 |
| Primary qHTS for inhibitors of SARS-S pseudo-typed particle cell entry | 39.8107 uM | pubchem.aid:1479145 |
| Primary qHTS to identify inhibitors of SARS-CoV-2 cell entry | 39.8107 uM | pubchem.aid:1645846 |
| VP16 counterscreen qHTS for inhibitors of ROR gamma transcriptional activity | 12.5893 uM | pubchem.aid:2546 |
| Validation qHTS for agonist of cAMP-regulated guanine nucleotide exchange factor 3 (EPAC1) | 35.4813 uM | pubchem.aid:1645883 |
| Validation qHTS for agonist of cAMP-regulated guanine nucleotide exchange factor 3 (EPAC1) | 35.4813 uM | pubchem.aid:1645883 |
| Validation qHTS for antagonist of cAMP-regulated guanine nucleotide exchange factor 4 (EPAC2) | 56.2341 uM | pubchem.aid:1645886 |
| Validation qHTS for antagonist of cAMP-regulated guanine nucleotide exchange factor 4 (EPAC2) | 56.2341 uM | pubchem.aid:1645886 |
| qHTS Assay for Inhibitors of Histone Lysine Methyltransferase G9a | 3.5481 uM | pubchem.aid:504332 |
| qHTS Assay for Small Molecule Inhibitors of the Human hERG Channel Activity | 35.4813 uM | pubchem.aid:588834 |
| qHTS assay for identifying genotoxic compounds that show differential cytotoxicity against isogenic chicken DT40 cell lines with known DNA damage response pathways - Rad54/Ku70 mutant cell line | 26.6032 uM | pubchem.aid:743015 |
| qHTS assay for identifying genotoxic compounds that show differential cytotoxicity against isogenic chicken DT40 cell lines with known DNA damage response pathways - Rev3 mutant cell line | 23.7101 uM | pubchem.aid:743014 |
| qHTS assay for identifying genotoxic compounds that show differential cytotoxicity against isogenic chicken DT40 cell lines with known DNA damage response pathways - wild type cell line | 18.8336 uM | pubchem.aid:743012 |
| qHTS assay for small molecule agonists of the p53 signaling pathway | 26.6032 uM | pubchem.aid:651631 |
| qHTS assay for small molecule agonists of the p53 signaling pathway - cell viability | 33.4915 uM | pubchem.aid:651633 |
| qHTS assay for small molecule disruptors of the mitochondrial membrane potential | 2.9849 uM | pubchem.aid:720635 |
| qHTS assay for small molecule disruptors of the mitochondrial membrane potential - cell viability | 10.5909 uM | pubchem.aid:720634 |
Elsewhere in the fleet
- AntibioticMech — CHEBI:32079 (same structure, same inchikey)
Provenance
| Source concept | Source | Version |
|---|---|---|
| BGC0000924 | MIBIG | 5 |
| CHEBI:32079 | CHEBI | 3-star |
This page is generated from data/natural_products/alkaloids/pyrrolnitrin.yaml, which is generated from the committed inventories. Neither is edited by hand.