(−)-marinopyrrole A

CHEBI:66678 ·resolve ·ANTIBACTERIAL ·EXACT SEEDED

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. — ChEBI

Machine-generated and unreviewed. Identity, structure and cross-references come straight from ChEBI's and CARD's own data; no curator has signed off on this record yet.

Classification

Strictly broader compounds or drug classes this molecule belongs to.

Label unavailable CHEBI:26455
Label unavailable CHEBI:33853
Label unavailable CHEBI:36683
Label unavailable CHEBI:76224

Chemical structure

Computed structure properties
Molecular formula	C22H12Cl4N2O4
Charge	0
Average mass	510.16 Da
Monoisotopic mass	507.95512 Da
Source	ChEBI
InChIKey	QYPJBTMRYKRTFG-UHFFFAOYSA-N

SMILES

O=C(c1ccccc1O)c1nc(Cl)c(Cl)c1-n1c(C(=O)c2ccccc2O)cc(Cl)c1Cl

InChI

InChI=1S/C22H12Cl4N2O4/c23-12-9-13(19(31)10-5-1-3-7-14(10)29)28(22(12)26)18-16(24)21(25)27-17(18)20(32)11-6-2-4-8-15(11)30/h1-9,27,29-30H

Also called

(4,4',5,5'-tetrachloro-1'H-1,3'-bipyrrole-2,2'-diyl)bis[(2-hydroxyphenyl)methanone] (EXACT_SYNONYM)— chebi

Cross-references

Identifiers for this same structure in other resources. An accession that lands on two different structures in this corpus is withheld from both rather than shown here, since it names at most one of them.

reaxys:11303256

Activity roles

Every antimicrobial role a source asserts for this compound — the unreduced evidence behind its antimicrobial_class.

antimicrobial agent CHEBI:33281
antibacterial agent CHEBI:33282

Source concepts

Every upstream concept that resolved to this record. The merge is the product: this is what shows ChEBI and CARD are describing the same structure.

Upstream concepts merged into this record
Source	Native ID	Label	Minted CURIE	Version
CHEBI	`CHEBI:66678`	(−)-marinopyrrole A	`antibioticmech:chebi-9d0fd62ec7`	2026-08-30

Producer organisms

Organisms that biosynthesize this compound. Cluster link evidence is how the upstream source graded the gene cluster, so it is populated only for a source that grades it. An empty cell is not weaker support: a curator-authored producer carries its support in Evidence instead. Where the source entry named several compounds, the evidence is marked inherited, meaning it covers this compound together with the cluster's other products rather than singling it out. Those products need not be related to each other: a cluster can list an intermediate, a precursor and a finished antibiotic side by side.

Producer organisms
Organism	BGC	Cluster link evidence	Source	Quality	Note	Evidence
Streptomyces sp. NCBITaxon:467194 strain CNQ-418	BGC0001159	Heterologous expression; Knock-out studies cluster inherited	MIBIG 4.0.1 (entry 5)	questionable	MIBiG active entry; compound 'marinopyrrole A' joined by exact Standard InChIKey.	PMID:22800473 (MIBiG's first legacy reference for the entry, inherited rather than attached to the compound. It supports that the entry exists; it is NOT established as evidence for this specific producer/compound link.)

Curation history

SEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Seeded from data/raw/ inventories (CHEBI)
RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-09-08 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-09-08 · seed_from_sources
Re-seeded from updated data/raw/ inventories

Provenance

Seeded by scripts/seed_from_sources.py from the committed inventories in data/raw/. View the record (YAML).

Explore across X-Mech: MediaIngredientMech ((−)-marinopyrrole A) · CultureMech · NaturalProductMech · PathwayMech · TraitMech · TaxonMech (Streptomyces sp.)