(−)-marinopyrrole A

CHEBI:66678 EXACT SEEDED antibacterial

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REVIEWED records curator sign-off on identity, structure, filing class and producer claims; DEPRECATED retains a superseded or out-of-scope record.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 member of the class of pyrroles that is 1'H-1,3'-bipyrrole substituted by 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	QYPJBTMRYKRTFG-UHFFFAOYSA-N
SMILES	OC1=CC=CC=C1C(=O)C1=CC(Cl)=C(Cl)N1C1=C(NC(Cl)=C1Cl)C(=O)C1=CC=CC=C1O
Stereochemistry	fully defined
Cross-references	npatlas:NPA03314

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.

Biosynthesis curated

Written by a curator with claim-level evidence on each step; not derived from a source. This is what the rest of the record exists to support.

Step	Enzyme	Reaction	Substrate → product	Evidence
1	Mpy16 UniProtKB:J7H1A1		ungrounded → ungrounded	DOI:10.1021/ja305670f
2	Mpy1/Mpy10/Mpy11 oxidative homocoupling module		ungrounded → ungrounded	DOI:10.1021/ja305670f

Step 1: This curates Mpy16 as the proposed initiating pyrrolyl-carrier-protein dichlorinase in the Streptomyces sp. CNQ-418 mpy pathway; the exact carrier-protein-tethered substrate and product remain ungrounded.

Step 2: This curates the genetically supported Mpy1/Mpy10/Mpy11 module that couples monodeoxypyoluteorin toward dimeric marinopyrroles 1-4, including major product marinopyrrole A; enzyme_id is intentionally omitted because the step requires two FADH2-dependent halogenases plus the pathway-specific flavin reductase rather than one protein accession.

Mechanism & Biosynthesis Overview

Causal graph — biosynthesis 9 nodes, 7 edges

Partial Streptomyces sp. CNQ-418 marinopyrrole A biosynthesis graph for Mpy16 pyrrole dichlorination and Mpy1/Mpy10/Mpy11-dependent N,C-bipyrrole homocoupling.

Subject	Predicate	Object	Notes	Evidence
pyrrolyl-S-carrier protein	is proposed to be dichlorinated by	Mpy16 FADH2-dependent halogenase	The mpy16 deletion supports a required early role, while the pyrrolyl-carrier-protein dichlorination assignment is by homology to the characterized pyoluteorin PltA.	DOI:10.1021/ja305670f https://www.uniprot.org/uniprotkb/J7H1A1 https://www.ncbi.nlm.nih.gov/protein/AFP87533.1 reference DOI:10.1021/ja305670f evidence type PRIMARY_EXPERIMENT snippet the mpy16 gene deletion completely abolished production of the marinopyrroles notes Yamanaka et al. deleted mpy16 from the heterologous Streptomyces coelicolor mpy expression system and used homology to pyoluteorin PltA to propose that Mpy16 performs the initiating pyrrolyl-carrier-protein dichlorination. reference https://www.uniprot.org/uniprotkb/J7H1A1 evidence type DATABASE_ASSERTION retrieved on 2026-09-27 notes UniProtKB:J7H1A1 is the unreviewed 447 aa Streptomyces sp. CNQ-418 Mpy16 FADH2-dependent halogenase entry, gene mpy16, cross-references EMBL JX157625, and links to PDB 5BUK. reference https://www.ncbi.nlm.nih.gov/protein/AFP87533.1 evidence type DATABASE_ASSERTION retrieved on 2026-09-27 notes NCBI GenPept AFP87533.1 is the JX157625.1 mpy16 FADH2-dependent halogenase coding sequence from the Streptomyces sp. CNQ-418 mpy cluster.
Mpy16 FADH2-dependent halogenase	forms	dichloropyrrolyl-S-carrier protein	The exact carrier-protein-bound product is left ungrounded because Yamanaka et al. proposed this initiating step from genetics and PltA homology.	DOI:10.1021/ja305670f https://www.uniprot.org/uniprotkb/J7H1A1 https://www.ncbi.nlm.nih.gov/protein/AFP87533.1 reference DOI:10.1021/ja305670f evidence type PRIMARY_EXPERIMENT snippet the mpy16 gene deletion completely abolished production of the marinopyrroles notes Yamanaka et al. deleted mpy16 from the heterologous Streptomyces coelicolor mpy expression system and used homology to pyoluteorin PltA to propose that Mpy16 performs the initiating pyrrolyl-carrier-protein dichlorination. reference https://www.uniprot.org/uniprotkb/J7H1A1 evidence type DATABASE_ASSERTION retrieved on 2026-09-27 notes UniProtKB:J7H1A1 is the unreviewed 447 aa Streptomyces sp. CNQ-418 Mpy16 FADH2-dependent halogenase entry, gene mpy16, cross-references EMBL JX157625, and links to PDB 5BUK. reference https://www.ncbi.nlm.nih.gov/protein/AFP87533.1 evidence type DATABASE_ASSERTION retrieved on 2026-09-27 notes NCBI GenPept AFP87533.1 is the JX157625.1 mpy16 FADH2-dependent halogenase coding sequence from the Streptomyces sp. CNQ-418 mpy cluster.
monodeoxypyoluteorin	is coupled during	N,C-bipyrrole homocoupling	Chemical complementation of an mpy6 deletion mutant with monodeoxypyoluteorin restored dimeric marinopyrrole 1-4 synthesis.	DOI:10.1021/ja305670f reference DOI:10.1021/ja305670f evidence type PRIMARY_EXPERIMENT snippet Chemical complementation of the mutant with 7 restored dimeric marinopyrrole synthesis notes Yamanaka et al. used the mpy6 deletion mutant to test monodeoxypyoluteorin, compound 7, as a precursor for dimeric marinopyrroles 1-4.
Mpy1 flavin reductase	supplies reduced flavin for	N,C-bipyrrole homocoupling	The mpy1 flavin reductase deletion strongly reduced dimeric marinopyrroles and accumulated monodeoxypyoluteorin.	DOI:10.1021/ja305670f reference DOI:10.1021/ja305670f evidence type PRIMARY_EXPERIMENT snippet Mpy10 and Mpy11 in the presence of the pathway specific flavin reductase Mpy1 notes Deletion and complementation in the heterologous S. coelicolor mpy system supported the requirement for Mpy10 and Mpy11 plus Mpy1 flavin reductase participation in dimeric marinopyrrole 1-4 formation.
Mpy10 FADH2-dependent halogenase	is required for	N,C-bipyrrole homocoupling	Deleting mpy10 abolished dimeric marinopyrrole 1-4 production and overproduced monodeoxypyoluteorin.	DOI:10.1021/ja305670f reference DOI:10.1021/ja305670f evidence type PRIMARY_EXPERIMENT snippet Mpy10 and Mpy11 in the presence of the pathway specific flavin reductase Mpy1 notes Deletion and complementation in the heterologous S. coelicolor mpy system supported the requirement for Mpy10 and Mpy11 plus Mpy1 flavin reductase participation in dimeric marinopyrrole 1-4 formation.
Mpy11 FADH2-dependent halogenase	is required for	N,C-bipyrrole homocoupling	Deleting mpy11 abolished dimeric marinopyrrole 1-4 production and overproduced monodeoxypyoluteorin.	DOI:10.1021/ja305670f reference DOI:10.1021/ja305670f evidence type PRIMARY_EXPERIMENT snippet Mpy10 and Mpy11 in the presence of the pathway specific flavin reductase Mpy1 notes Deletion and complementation in the heterologous S. coelicolor mpy system supported the requirement for Mpy10 and Mpy11 plus Mpy1 flavin reductase participation in dimeric marinopyrrole 1-4 formation.
N,C-bipyrrole homocoupling	forms	(-)-marinopyrrole A	The reconstituted mpy cluster produced dimeric marinopyrroles 1-4 in S. coelicolor, with marinopyrrole A as the major metabolite.	DOI:10.1021/ja305670f reference DOI:10.1021/ja305670f evidence type PRIMARY_EXPERIMENT snippet production of dimeric marinopyrroles 1-4 notes Yamanaka et al. expressed the reconstituted Streptomyces sp. CNQ-418 mpy cluster in Streptomyces coelicolor M512, detected dimeric marinopyrroles 1-4, and reported marinopyrrole A as the major metabolite.

Every edge carries its own citation; an uncited edge is refused by the corpus tests.

Elsewhere in the fleet

AntibioticMech — CHEBI:66678 (same structure, same inchikey)

Explore across X-Mech

AntibioticMech ((−)-marinopyrrole A) ↗ MediaIngredientMech (CHEBI:66678) ↗ TaxonMech: Streptomyces sp. CNQ-418 (NCBITaxon:467194) ↗ PathwayMech (mibig:BGC0001159) ↗

Provenance

Source concept	Source	Version
BGC0001159	MIBIG	5
CHEBI:66678	CHEBI	3-star

This page is generated from data/natural_products/alkaloids/marinopyrrole-a.yaml, which is generated from the committed inventories. Neither is edited by hand.