toxoflavin
CHEBI:80729 EXACT SEEDED antibacterialcytotoxicenzyme inhibitor
A pyrimidotriazine that is 1,6-dimethyl-1,5,6,7-tetrahydropyrimido[5,4-e][1,2,4]triazine with oxo groups at positions 5 and 7.
Structure
| Standard InChIKey | SLGRAIAQIAUZAQ-UHFFFAOYSA-N |
|---|---|
| SMILES | CN1N=CN=C2C(=O)N(C)C(=O)N=C12 |
| Stereochemistry | fully defined |
| Cross-references | npatlas:NPA04485, pubchem:66541 |
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 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 |
|---|---|---|---|
| Burkholderia glumae NCBITaxon:337 |
SOURCE_ASSERTION | mibig:BGC0000929 | DOI:10.1007/s10327-003-0096-1 |
| Streptomyces hiroshimensis NCBITaxon:66424 |
SOURCE_ASSERTION | mibig:BGC0001972 | PMID:30565634 |
Occurrences 4
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 |
|---|---|---|
| Burkholderia gladioli NCBITaxon:28095 |
CHEBI | PMID:5905124 |
| Burkholderia glumae NCBITaxon:337 |
LOTUS | DOI:10.1007/S10327-003-0096-1 |
| Burkholderia glumae NCBITaxon:337 |
CHEBI | Jeong, Y., Kim, J., Kim, S., and Kang, Y (2003). Toxoflavin Produced by Burkholderia glumae Causing Rice Grain Rot Is Responsible for Inducing Bacterial Wilt in Many Field Crops. Plant Disease, Vol. 87 (8). p 890-895. |
| Streptomyces hiroshimensis NCBITaxon:66424 |
LOTUS | DOI:10.1039/C8OB02847H |
Biosynthetic gene clusters 2
| Accession | Host | Locus evidence | Genome |
|---|---|---|---|
| mibig:BGC0000929 | Burkholderia glumae NCBITaxon:337 |
CLUSTER_UNSTATED | genbank:EF587764.1 |
| mibig:BGC0001972 | Streptomyces hiroshimensis NCBITaxon:66424 |
CLUSTER_UNSTATED | genbank:MK256951.1 |
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 Cell Based Secondary Assay To Explore Cytotoxicity of Compounds that Inhibit Mycobacterium Tuberculosis | 7.979 uM | pubchem.aid:435019 |
| A High Throughput Confirmatory Assay used to Identify Novel Compounds that Inhibit Mycobacterium Tuberculosis in the absence of Glycerol | IC50 2.84 uM | pubchem.aid:449764 |
| A counter screen for small molecule screen for inhibitors of the PhoP regulon in Salmonella typhi | IC50 2.53 uM | pubchem.aid:2384 |
| A cytotoxicity screen of small molecule inhibitors of the PhoP regulon in Salmonella typhi identified in the primary screen | EC50 1.38 uM | pubchem.aid:2252 |
| A quantitative high throughput screen for small molecules that induce DNA re-replication in MCF 10a normal breast cells. | 18.3564 uM | pubchem.aid:624296 |
| A screen for inhibitors of the PhoP regulon in Salmonella Typhi using a modified counterscreen | IC50 0.741 uM | pubchem.aid:1985 |
| A small molecule screen for inhibitors of the PhoP regulon in Salmonella typhi | IC50 1.29 uM | pubchem.aid:1850 |
| ATP-based Luminescence in the Absence of Cytokines Measured in Cell-Based System Using Plate Reader - 2061-06_Inhibitor_Dose_CherryPick | EC50 1.484 uM | pubchem.aid:463229 |
| AlphaScreen Assay from US Patent US9284299: "Substituted 1H-indazol-1-ol analogs as inhibitors of beta catenin/Tcf protein-protein interactions" | KI 3.65 uM | pubchem.aid:1802420 |
| AlphaScreen Assay from US Patent US9284299: "Substituted 1H-indazol-1-ol analogs as inhibitors of beta catenin/Tcf protein-protein interactions" | KI 3.65 uM | pubchem.aid:1802420 |
| AlphaScreen Assay from US Patent US9284299: "Substituted 1H-indazol-1-ol analogs as inhibitors of beta catenin/Tcf protein-protein interactions" | KI 19.94 uM | pubchem.aid:1802420 |
| AlphaScreen Assay from US Patent US9284299: "Substituted 1H-indazol-1-ol analogs as inhibitors of beta catenin/Tcf protein-protein interactions" | KI 66.23 uM | pubchem.aid:1802420 |
| AlphaScreen Assay from US Patent US9284299: "Substituted 1H-indazol-1-ol analogs as inhibitors of beta catenin/Tcf protein-protein interactions" | KI 19.94 uM | pubchem.aid:1802420 |
| AlphaScreen Assay from US Patent US9284299: "Substituted 1H-indazol-1-ol analogs as inhibitors of beta catenin/Tcf protein-protein interactions" | KI 66.23 uM | pubchem.aid:1802420 |
| AlphaScreen Assay from US Patent US9738628: "Substituted 1H-indazol-1-OL analogs as inhibitors of beta catenin/Tcf protein-protein interactions" | KI 5.82 uM | pubchem.aid:1797021 |
| Cathepsin B dose-response confirmation | IC50 0.0461 uM | pubchem.aid:820 |
| Cathepsin B mixture HTS dose-response confirmation | IC50 0.04729 uM | pubchem.aid:830 |
| Cathepsin L dose-response confirmation | IC50 0.22581 uM | pubchem.aid:825 |
| Cathepsin L dose-response testing in the presence of cysteine | IC50 50 uM | pubchem.aid:1627 |
| Cathepsin S dose-response confirmation | IC50 0.176463 uM | pubchem.aid:831 |
| Cell-based secondary assay for identifying Hsp90 inhibitors that degrade Hsp90 client protein Her2 | IC50 1.875 uM | pubchem.aid:754 |
| Cell-based secondary assay for identifying Hsp90 inhibitors that degrade Hsp90 client protein Her2 | IC50 1.875 uM | pubchem.aid:754 |
| Concentration response confirmation VP16 counterscreen for inhibitors of ROR gamma transcriptional activity | 0.4449 uM | pubchem.aid:2763 |
| Concentration response confirmation assay for inhibitors of ROR gamma transcriptional activity | 0.996 uM | pubchem.aid:2762 |
| Concentration-Response Counterscreen for Redox Active Inhibitors of Caspase-1: Catalase | 1.122 uM | pubchem.aid:888 |
Elsewhere in the fleet
- AntibioticMech — CHEBI:80729 (same structure, same inchikey)
Open questions 2
name-disagreement — ChEBI calls this structure 'toxoflavin' and MIBiG calls it 'xanthothricin'. They share a Standard InChIKey, so if the names denote different compounds then one upstream record has the wrong structure. Check which.
shared-structure — This structure is reported by more than one MIBiG entry: BGC0000929, BGC0001972. Confirm they describe the same compound rather than an upstream cross-reference error.
Provenance
| Source concept | Source | Version |
|---|---|---|
| BGC0000929 | MIBIG | 3 |
| BGC0001972 | MIBIG | 4 |
| CHEBI:80729 | CHEBI | 3-star |
This page is generated from data/natural_products/alkaloids/toxoflavin.yaml, which is generated from the committed inventories. Neither is edited by hand.