violacein
CHEBI:131914 EXACT SEEDED antibacterial
A member of the class of hydroxyindoles resulting from the formal oxidative coupling between the 3-position of 1,3-dihydro-2H-indol-2-one and the 3-position of 1,3-dihydro-2H-pyrrol-2-one, which is substituted at the 5 position by a 5-hydroxy-1H-indol-3-yl group, where the newly-formed double bond has E configuration. It is a purple chromobacterial pigment that has antibacterial, antifungal, antiprotozoan, and anticancer properties.
Structure
| Standard InChIKey | XAPNKXIRQFHCHN-QGOAFFKASA-N |
|---|---|
| SMILES | C1=CC=C2C(=C1)/C(=C\3/C=C(NC3=O)C4=CNC5=C4C=C(C=C5)O)/C(=O)N2 |
| Stereochemistry | fully defined |
| Cross-references | pubchem:9928039 |
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 |
|---|---|---|---|
| Duganella sp. B2 NCBITaxon:445969 |
SOURCE_ASSERTION | mibig:BGC0000831 | PMID:22391969 |
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 |
|---|---|---|
| Pseudoalteromonas tunicata NCBITaxon:314281 |
LOTUS | DOI:10.3390/10101286 |
| Chromobacterium violaceum NCBITaxon:536 |
LOTUS | DOI:10.1021/BI061998Z |
| Chromobacterium violaceum NCBITaxon:536 |
CHEBI | PMID:17176066 |
| Escherichia coli NCBITaxon:562 |
LOTUS | DOI:10.1021/OL0509585 |
Biosynthetic gene clusters 1
| Accession | Host | Locus evidence | Genome |
|---|---|---|---|
| mibig:BGC0000831 | Duganella sp. B2 NCBITaxon:445969 |
CLUSTER_UNSTATED | genbank:GQ266676.1 |
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.
Elsewhere in the fleet
- AntibioticMech — CHEBI:131914 (same structure, same inchikey)
Provenance
| Source concept | Source | Version |
|---|---|---|
| BGC0000831 | MIBIG | 3 |
| CHEBI:131914 | CHEBI | 3-star |
This page is generated from data/natural_products/alkaloids/violacein.yaml, which is generated from the committed inventories. Neither is edited by hand.