(−)-marinopyrrole B
CHEBI:66679 EXACT SEEDED antibacterial
A member of the class of pyrroles that is 1'H-1,3'-bipyrrole substituted by a bromo group at position 3, four chloro groups at positions 4, 4', 5 and 5' and two 2-hydroxybenzoyl moieties at positions 2 and 2'. It is isolated from Streptomyces sp.CNQ-418 and exhibits cytotoxic and antibacterial activities.
Structure
| Standard InChIKey | XAANSONIBUCODQ-UHFFFAOYSA-N |
|---|---|
| SMILES | OC1=CC=CC=C1C(=O)C1=C(N2C(Cl)=C(Cl)C(Br)=C2C(=O)C2=CC=CC=C2O)C(Cl)=C(Cl)N1 |
| Stereochemistry | fully defined |
| Cross-references | npatlas:NPA01154 |
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 nrps, pks, 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 |
|---|---|---|---|
| Streptomyces sp. CNQ-418 NCBITaxon:467194 |
BGC_CHARACTERIZED | mibig:BGC0001159 | PMID:22800473 |
Occurrences 3
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 NCBITaxon:1883 |
LOTUS | DOI:10.1021/OL702952N |
| Streptomyces NCBITaxon:1883 |
LOTUS | DOI:10.7164/ANTIBIOTICS.51.963 |
| Streptomyces sp. NCBITaxon:1931 |
CHEBI | PMID:18205372 |
Biosynthetic gene clusters 1
| Accession | Host | Locus evidence | Genome |
|---|---|---|---|
| mibig:BGC0001159 | Streptomyces sp. CNQ-418 NCBITaxon:467194 |
CLUSTER_DEMONSTRATED | genbank:JX157625.1 |
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:66679 (same structure, same inchikey)
Provenance
| Source concept | Source | Version |
|---|---|---|
| BGC0001159 | MIBIG | 5 |
| CHEBI:66679 | CHEBI | 3-star |
This page is generated from data/natural_products/alkaloids/marinopyrrole-b.yaml, which is generated from the committed inventories. Neither is edited by hand.