toxoflavin

CHEBI:80729 EXACT SEEDED antibacterialcytotoxicenzyme inhibitor

What these status tags mean

Curation status describes a workflow state. SEEDED means the record entered through the source-seeding workflow; it does not imply that no later curation occurred. PROPOSED marks an addition awaiting review; REVIEWED records curator sign-off on identity, structure, filing class and producer claims; DEPRECATED retains a superseded or out-of-scope record. These are workflow decisions, not independently verified human review. Agent-assisted contributions may appear in the record history.

Grounding describes the identifier mapping: EXACT uses an ontology identity asserted by the source; MINTED keeps a local identifier when no defensible ontology identity is available; REVIEW_NEEDED flags an exact structure whose ontology identity needs adjudication. The grounding note retains any unresolved alternatives. These tags do not establish the strength of producer or activity evidence.

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.

Mechanism & Biosynthesis Overview

Bioactivities 25

Entries preserve source qualifiers, targets and evidence. Repeated assay names or values are not independent replications; inspect source detail for differences.

Elsewhere in the fleet

AntibioticMech — CHEBI:80729 (same structure, same inchikey)

Explore across X-Mech

AntibioticMech (toxoflavin) ↗ MediaIngredientMech (CHEBI:80729) ↗ TaxonMech: Burkholderia glumae (NCBITaxon:337) ↗ TaxonMech: Streptomyces hiroshimensis (NCBITaxon:66424) ↗ PathwayMech (mibig:BGC0000929) ↗ PathwayMech (mibig:BGC0001972) ↗

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.

Assay	Result	Target enzyme	Source detail
A Cell Based Secondary Assay To Explore Cytotoxicity of Compounds that Inhibit Mycobacterium Tuberculosis	OTHER 7.979 uM; ACTIVE	Not recorded	pubchem.aid:435019 assay A Cell Based Secondary Assay To Explore Cytotoxicity of Compounds that Inhibit Mycobacterium Tuberculosis evidence reference pubchem.aid:435019 evidence type DATABASE_ASSERTION notes PubChem BioAssay AID 435019, deposited by Southern Research Specialized Biocontainment Screening Center; assay type Confirmatory. Source endpoint: CC50. call ACTIVE measurement type OTHER value 7.979 units uM activity class CYTOTOXIC
A High Throughput Confirmatory Assay used to Identify Novel Compounds that Inhibit Mycobacterium Tuberculosis in the absence of Glycerol	IC50 2.84 uM; ACTIVE	Not recorded	pubchem.aid:449764 assay A High Throughput Confirmatory Assay used to Identify Novel Compounds that Inhibit Mycobacterium Tuberculosis in the absence of Glycerol evidence reference pubchem.aid:449764 evidence type DATABASE_ASSERTION notes PubChem BioAssay AID 449764, deposited by Southern Research Specialized Biocontainment Screening Center; assay type Confirmatory. call ACTIVE measurement type IC50 value 2.84 units uM
A counter screen for small molecule screen for inhibitors of the PhoP regulon in Salmonella typhi	IC50 2.53 uM; ACTIVE	Not recorded	pubchem.aid:2384 assay A counter screen for small molecule screen for inhibitors of the PhoP regulon in Salmonella typhi evidence reference pubchem.aid:2384 evidence type DATABASE_ASSERTION notes PubChem BioAssay AID 2384, deposited by Southern Research Specialized Biocontainment Screening Center; assay type Confirmatory. call ACTIVE measurement type IC50 value 2.53 units uM activity class ENZYME_INHIBITOR
A cytotoxicity screen of small molecule inhibitors of the PhoP regulon in Salmonella typhi identified in the primary screen	EC50 1.38 uM; ACTIVE	Not recorded	pubchem.aid:2252 assay A cytotoxicity screen of small molecule inhibitors of the PhoP regulon in Salmonella typhi identified in the primary screen evidence reference pubchem.aid:2252 evidence type DATABASE_ASSERTION notes PubChem BioAssay AID 2252, deposited by Southern Research Specialized Biocontainment Screening Center; assay type Confirmatory. call ACTIVE measurement type EC50 value 1.38 units uM activity class CYTOTOXIC
A quantitative high throughput screen for small molecules that induce DNA re-replication in MCF 10a normal breast cells.	OTHER 18.3564 uM; ACTIVE	Not recorded	pubchem.aid:624296 assay A quantitative high throughput screen for small molecules that induce DNA re-replication in MCF 10a normal breast cells. evidence reference pubchem.aid:624296 evidence type DATABASE_ASSERTION notes PubChem BioAssay AID 624296, deposited by NCGC; assay type Confirmatory. Source endpoint: Potency. Target accession NP_056979 was left ungrounded because PubChem did not provide a UniProtKB accession. call ACTIVE measurement type OTHER value 18.3564 units uM
A screen for inhibitors of the PhoP regulon in Salmonella Typhi using a modified counterscreen	IC50 0.741 uM; ACTIVE	Not recorded	pubchem.aid:1985 assay A screen for inhibitors of the PhoP regulon in Salmonella Typhi using a modified counterscreen evidence reference pubchem.aid:1985 evidence type DATABASE_ASSERTION notes PubChem BioAssay AID 1985, deposited by Southern Research Specialized Biocontainment Screening Center; assay type Confirmatory. call ACTIVE measurement type IC50 value 0.741 units uM activity class ENZYME_INHIBITOR
A small molecule screen for inhibitors of the PhoP regulon in Salmonella typhi	IC50 1.29 uM; ACTIVE	Not recorded	pubchem.aid:1850 assay A small molecule screen for inhibitors of the PhoP regulon in Salmonella typhi evidence reference pubchem.aid:1850 evidence type DATABASE_ASSERTION notes PubChem BioAssay AID 1850, deposited by Southern Research Specialized Biocontainment Screening Center; assay type Confirmatory. call ACTIVE measurement type IC50 value 1.29 units uM activity class ENZYME_INHIBITOR
ATP-based Luminescence in the Absence of Cytokines Measured in Cell-Based System Using Plate Reader - 2061-06_Inhibitor_Dose_CherryPick	OTHER 1.484 uM; ACTIVE	Not recorded	pubchem.aid:463229 assay ATP-based Luminescence in the Absence of Cytokines Measured in Cell-Based System Using Plate Reader - 2061-06_Inhibitor_Dose_CherryPick evidence reference pubchem.aid:463229 evidence type DATABASE_ASSERTION notes PubChem BioAssay AID 463229, deposited by Broad Institute; assay type Confirmatory. Source endpoint: AC50. call ACTIVE measurement type OTHER value 1.484 units uM
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; ACTIVE	UniProtKB:P15884	pubchem.aid:1802420 assay AlphaScreen Assay from US Patent US9284299: "Substituted 1H-indazol-1-ol analogs as inhibitors of beta catenin/Tcf protein-protein interactions" evidence reference pubchem.aid:1802420 evidence type DATABASE_ASSERTION notes PubChem BioAssay AID 1802420, deposited by BindingDB; assay type Confirmatory. call ACTIVE measurement type KI value 3.65 units uM target enzyme UniProtKB:P15884 activity class ENZYME_INHIBITOR
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; ACTIVE	UniProtKB:P35222	pubchem.aid:1802420 assay AlphaScreen Assay from US Patent US9284299: "Substituted 1H-indazol-1-ol analogs as inhibitors of beta catenin/Tcf protein-protein interactions" evidence reference pubchem.aid:1802420 evidence type DATABASE_ASSERTION notes PubChem BioAssay AID 1802420, deposited by BindingDB; assay type Confirmatory. call ACTIVE measurement type KI value 3.65 units uM target enzyme UniProtKB:P35222 activity class ENZYME_INHIBITOR
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; INACTIVE	UniProtKB:P12830	pubchem.aid:1802420 assay AlphaScreen Assay from US Patent US9284299: "Substituted 1H-indazol-1-ol analogs as inhibitors of beta catenin/Tcf protein-protein interactions" evidence reference pubchem.aid:1802420 evidence type DATABASE_ASSERTION notes PubChem BioAssay AID 1802420, deposited by BindingDB; assay type Confirmatory. call INACTIVE measurement type KI value 19.94 units uM target enzyme UniProtKB:P12830
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; INACTIVE	UniProtKB:P25054	pubchem.aid:1802420 assay AlphaScreen Assay from US Patent US9284299: "Substituted 1H-indazol-1-ol analogs as inhibitors of beta catenin/Tcf protein-protein interactions" evidence reference pubchem.aid:1802420 evidence type DATABASE_ASSERTION notes PubChem BioAssay AID 1802420, deposited by BindingDB; assay type Confirmatory. call INACTIVE measurement type KI value 66.23 units uM target enzyme UniProtKB:P25054
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; INACTIVE	UniProtKB:P35222	pubchem.aid:1802420 assay AlphaScreen Assay from US Patent US9284299: "Substituted 1H-indazol-1-ol analogs as inhibitors of beta catenin/Tcf protein-protein interactions" evidence reference pubchem.aid:1802420 evidence type DATABASE_ASSERTION notes PubChem BioAssay AID 1802420, deposited by BindingDB; assay type Confirmatory. call INACTIVE measurement type KI value 19.94 units uM target enzyme UniProtKB:P35222
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; INACTIVE	UniProtKB:P35222	pubchem.aid:1802420 assay AlphaScreen Assay from US Patent US9284299: "Substituted 1H-indazol-1-ol analogs as inhibitors of beta catenin/Tcf protein-protein interactions" evidence reference pubchem.aid:1802420 evidence type DATABASE_ASSERTION notes PubChem BioAssay AID 1802420, deposited by BindingDB; assay type Confirmatory. call INACTIVE measurement type KI value 66.23 units uM target enzyme UniProtKB:P35222
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; ACTIVE	UniProtKB:P35222	pubchem.aid:1797021 assay AlphaScreen Assay from US Patent US9738628: "Substituted 1H-indazol-1-OL analogs as inhibitors of beta catenin/Tcf protein-protein interactions" evidence reference pubchem.aid:1797021 evidence type DATABASE_ASSERTION notes PubChem BioAssay AID 1797021, deposited by BindingDB; assay type Confirmatory. call ACTIVE measurement type KI value 5.82 units uM target enzyme UniProtKB:P35222 activity class ENZYME_INHIBITOR
Cathepsin B dose-response confirmation	IC50 0.0461 uM; ACTIVE	Not recorded	pubchem.aid:820 assay Cathepsin B dose-response confirmation evidence reference pubchem.aid:820 evidence type DATABASE_ASSERTION notes PubChem BioAssay AID 820, deposited by PCMD; assay type Confirmatory. Target accession AAH95408 was left ungrounded because PubChem did not provide a UniProtKB accession. call ACTIVE measurement type IC50 value 0.0461 units uM
Cathepsin B mixture HTS dose-response confirmation	IC50 0.04729 uM; NOT_DETERMINED	Not recorded	pubchem.aid:830 assay Cathepsin B mixture HTS dose-response confirmation evidence reference pubchem.aid:830 evidence type DATABASE_ASSERTION notes PubChem BioAssay AID 830, deposited by PCMD; assay type Confirmatory. Source outcome: Inconclusive. Target accession AAH95408 was left ungrounded because PubChem did not provide a UniProtKB accession. call NOT_DETERMINED measurement type IC50 value 0.04729 units uM
Cathepsin L dose-response confirmation	IC50 0.22581 uM; ACTIVE	Not recorded	pubchem.aid:825 assay Cathepsin L dose-response confirmation evidence reference pubchem.aid:825 evidence type DATABASE_ASSERTION notes PubChem BioAssay AID 825, deposited by PCMD; assay type Confirmatory. Target accession NP_001903 was left ungrounded because PubChem did not provide a UniProtKB accession. call ACTIVE measurement type IC50 value 0.22581 units uM
Cathepsin L dose-response testing in the presence of cysteine	IC50 50 uM; INACTIVE	Not recorded	pubchem.aid:1627 assay Cathepsin L dose-response testing in the presence of cysteine evidence reference pubchem.aid:1627 evidence type DATABASE_ASSERTION notes PubChem BioAssay AID 1627, deposited by PCMD; assay type Confirmatory. Target accession NP_001903 was left ungrounded because PubChem did not provide a UniProtKB accession. call INACTIVE measurement type IC50 value 50.0 units uM
Cathepsin S dose-response confirmation	IC50 0.176463 uM; ACTIVE	Not recorded	pubchem.aid:831 assay Cathepsin S dose-response confirmation evidence reference pubchem.aid:831 evidence type DATABASE_ASSERTION notes PubChem BioAssay AID 831, deposited by PCMD; assay type Confirmatory. Target accession NP_004070 was left ungrounded because PubChem did not provide a UniProtKB accession. call ACTIVE measurement type IC50 value 0.176463 units uM
Cell-based secondary assay for identifying Hsp90 inhibitors that degrade Hsp90 client protein Her2	IC50 1.875 uM; ACTIVE	Not recorded	pubchem.aid:754 assay Cell-based secondary assay for identifying Hsp90 inhibitors that degrade Hsp90 client protein Her2 evidence reference pubchem.aid:754 evidence type DATABASE_ASSERTION notes PubChem BioAssay AID 754, deposited by Emory University Molecular Libraries Screening Center; assay type Confirmatory. Target accession AAD14062 was left ungrounded because PubChem did not provide a UniProtKB accession. call ACTIVE measurement type IC50 value 1.875 units uM
Cell-based secondary assay for identifying Hsp90 inhibitors that degrade Hsp90 client protein Her2	IC50 1.875 uM; ACTIVE	Not recorded	pubchem.aid:754 assay Cell-based secondary assay for identifying Hsp90 inhibitors that degrade Hsp90 client protein Her2 evidence reference pubchem.aid:754 evidence type DATABASE_ASSERTION notes PubChem BioAssay AID 754, deposited by Emory University Molecular Libraries Screening Center; assay type Confirmatory. Target accession NP_005339 was left ungrounded because PubChem did not provide a UniProtKB accession. call ACTIVE measurement type IC50 value 1.875 units uM
Concentration response confirmation VP16 counterscreen for inhibitors of ROR gamma transcriptional activity	OTHER 0.4449 uM; ACTIVE	Not recorded	pubchem.aid:2763 assay Concentration response confirmation VP16 counterscreen for inhibitors of ROR gamma transcriptional activity evidence reference pubchem.aid:2763 evidence type DATABASE_ASSERTION notes PubChem BioAssay AID 2763, deposited by NCGC; assay type Confirmatory. Source endpoint: Potency. Target accession NP_035411 was left ungrounded because PubChem did not provide a UniProtKB accession. call ACTIVE measurement type OTHER value 0.4449 units uM activity class ENZYME_INHIBITOR
Concentration response confirmation assay for inhibitors of ROR gamma transcriptional activity	OTHER 0.996 uM; ACTIVE	Not recorded	pubchem.aid:2762 assay Concentration response confirmation assay for inhibitors of ROR gamma transcriptional activity evidence reference pubchem.aid:2762 evidence type DATABASE_ASSERTION notes PubChem BioAssay AID 2762, deposited by NCGC; assay type Confirmatory. Source endpoint: Potency. Target accession NP_035411 was left ungrounded because PubChem did not provide a UniProtKB accession. call ACTIVE measurement type OTHER value 0.996 units uM activity class ENZYME_INHIBITOR
Concentration-Response Counterscreen for Redox Active Inhibitors of Caspase-1: Catalase	OTHER 1.122 uM; ACTIVE	UniProtKB:P29466	pubchem.aid:888 assay Concentration-Response Counterscreen for Redox Active Inhibitors of Caspase-1: Catalase evidence reference pubchem.aid:888 evidence type DATABASE_ASSERTION notes PubChem BioAssay AID 888, deposited by NCGC; assay type Confirmatory. Source endpoint: Potency. call ACTIVE measurement type OTHER value 1.122 units uM target enzyme UniProtKB:P29466 activity class ENZYME_INHIBITOR notes 336 further PubChem assay results are in data/raw/pubchem_bioassay.tsv but not written here.