2,4-diacetylphloroglucinol
CHEBI:78688 EXACT SEEDED antifungalantiviralcytotoxicenzyme inhibitor
A benzenetriol that is phloroglucinol in which two of the ring hydrogens are replaced by acetyl groups.
Structure
| Standard InChIKey | PIFFQYJYNWXNGE-UHFFFAOYSA-N |
|---|---|
| SMILES | CC(=O)C1=C(C(=C(C=C1O)O)C(=O)C)O |
| Stereochemistry | fully defined |
| Cross-references | pubchem:16547 |
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, from MIBiG.
Producer organisms 2
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 fluorescens NCBITaxon:294 |
BGC_CHARACTERIZED | mibig:BGC0000280 | PMID:15256586 |
| Pseudomonas fluorescens NCBITaxon:294 |
SOURCE_ASSERTION | mibig:BGC0000281 | PMID:10322017 |
Occurrences 9
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 fluorescens PF5 NCBITaxon:1218948 |
CHEBI | PMID:15826166 |
| Pseudomonas protegens PF5 NCBITaxon:220664 |
CHEBI | PMID:24742073 |
| Lysobacter gummosus NCBITaxon:262324 |
CHEBI | PMID:18058176 |
| Pseudomonas NCBITaxon:286 |
LOTUS | DOI:10.1128/AEM.00455-14 |
| Pseudomonas protegens NCBITaxon:380021 |
LOTUS | DOI:10.1094/MPMI-10-13-0311-R |
| Pseudomonas fluorescens NCBITaxon:294 |
LOTUS | DOI:10.1007/BF00633306 |
| Pseudomonas fluorescens NCBITaxon:294 |
LOTUS | DOI:10.1016/S0031-9422(00)97487-9 |
| Pseudomonas fluorescens NCBITaxon:294 |
LOTUS | DOI:10.1099/MIC.0.27033-0 |
| Pseudomonas fluorescens NCBITaxon:294 |
LOTUS | DOI:10.1128/JB.181.10.3155-3163.1999 |
Biosynthetic gene clusters 2
| Accession | Host | Locus evidence | Genome |
|---|---|---|---|
| mibig:BGC0000280 | Pseudomonas fluorescens NCBITaxon:294 |
CLUSTER_DEMONSTRATED | genbank:AF497760.1 |
| mibig:BGC0000281 | Pseudomonas fluorescens NCBITaxon:294 |
CLUSTER_UNSTATED | genbank:DQ083928.1 |
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 SW480 colon adenocarcinoma cells. | 1.4581 uM | pubchem.aid:624297 |
| Counterscreen for agonists of nuclear receptor subfamily 2, group E, member 3 (NR2E3):Luminescence-based cell-based high throughput dose response assay to identify inhibitors of the Herpes Virus Virion Protein 16 (VP16) | IC50 4.561 uM | pubchem.aid:624395 |
| High Throughput Screening for Foot and Mouth Disease Virus Antivirals | 35.4813 uM | pubchem.aid:1159524 |
| Luminescence Microorganism-Based Dose Confirmation HTS to Identify Compounds Cytotoxic to SK(-)GAS Group A Streptococcus | EC50 3.897 uM | pubchem.aid:1900 |
| Luminescence Microorganism-Based Dose Confirmation HTS to Identify Inhibitors of Streptokinase Promotor Activity | EC50 2.635 uM | pubchem.aid:1902 |
| Luminescence Microorganism-Based Dose Response HTS to Identify Compounds Cytotoxic to Streptococcus | EC50 3.976 uM | pubchem.aid:1915 |
| Luminescence-based cell-based high throughput dose response assay for agonists of nuclear receptor subfamily 2, group E, member 3 (NR2E3) | IC50 3.238 uM | pubchem.aid:624394 |
| Nrf2 qHTS screen for inhibitors | 25.929 uM | pubchem.aid:504444 |
| Primary qHTS for delayed death inhibitors of the malarial parasite plastid, 48 hour incubation | 10.4179 uM | pubchem.aid:504832 |
| VP16 counterscreen qHTS for inhibitors of ROR gamma transcriptional activity | 10 uM | pubchem.aid:2546 |
| Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression | 7.0795 uM | PMID:35787375 |
| Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression | 7.0795 uM | PMID:35787375 |
| qHTS Assay for Inhibitors of Hepatitis C Virus (HCV) | 3.5481 uM | pubchem.aid:651820 |
| qHTS Assay for Inhibitors of Influenza NS1 Protein Function | 10 uM | pubchem.aid:2326 |
| qHTS Assay for Lipid Storage Modulators in Drosophila S3 Cells | 16.3601 uM | pubchem.aid:2685 |
| qHTS Assay for Modulators of miRNAs and/or Inhibitors of miR-21 | 26.1216 uM | pubchem.aid:2289 |
| qHTS Assay for Modulators of miRNAs and/orActivators of miR-21 | 26.1216 uM | pubchem.aid:2288 |
| qHTS Assay for Small Molecule Inhibitors of Mitochondrial Division or Activators of Mitochondrial Fusion | 11.2202 uM | pubchem.aid:485298 |
| qHTS Assay to Find Inhibitors of Chronic Active B-Cell Receptor Signaling | 35.4813 uM | pubchem.aid:493014 |
| qHTS Assay to Find Inhibitors of Pin1 | 25.1189 uM | pubchem.aid:504891 |
| qHTS for Antagonists of gsp, the Etiologic Mutation Responsible for Fibrous Dysplasia/McCune-Albright Syndrome: qHTS | 35.4813 uM | pubchem.aid:624288 |
| qHTS for Inhibitors of TGF-b | 22.3872 uM | pubchem.aid:588855 |
| qHTS for Inhibitors of TGF-b: Cytotox Counterscreen | 3.9811 uM | pubchem.aid:588856 |
| qHTS for Inhibitors of human tyrosyl-DNA phosphodiesterase 1 (TDP1): qHTS in cells in absence of CPT | 25.929 uM | pubchem.aid:686978 |
| qHTS for Inhibitors of human tyrosyl-DNA phosphodiesterase 1 (TDP1): qHTS in cells in presence of CPT | 20.5962 uM | pubchem.aid:686979 |
Elsewhere in the fleet
- AntibioticMech — CHEBI:78688 (same structure, same inchikey)
Open questions 1
shared-structure — This structure is reported by more than one MIBiG entry: BGC0000280, BGC0000281. Confirm they describe the same compound rather than an upstream cross-reference error.
Provenance
| Source concept | Source | Version |
|---|---|---|
| BGC0000280 | MIBIG | 5 |
| BGC0000281 | MIBIG | 3 |
| CHEBI:78688 | CHEBI | 3-star |
This page is generated from data/natural_products/polyketides/2-4-diacetylphloroglucinol.yaml, which is generated from the committed inventories. Neither is edited by hand.