schizokinen

CHEBI:84582 EXACT SEEDED

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REVIEWED records curator sign-off on identity, structure, filing class and producer claims; DEPRECATED retains a superseded or out-of-scope record.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 hydroxamic acid resulting from the formal condensation of the primary amino group of N-(3-aminopropyl)-N-hydroxyacetamide (2 mol eq.) with the carboxy groups at positions 1 and 3 of citric acid. It is a siderophore produced by Bacillus megaterium and Anabaena species.

Structure

Standard InChIKey	YILWWVUXGMGOAM-UHFFFAOYSA-N
SMILES	CC(=O)N(O)CCCNC(=O)CC(O)(CC(=O)NCCCN(O)C(C)=O)C(=O)O
Stereochemistry	fully defined
Cross-references	pubchem:3082425, cyanometdb:CyanoMetDB_1678, npatlas:NPA027582

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, nrps, 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
Leptolyngbya sp. PCC 7376 NCBITaxon:111781	SOURCE_ASSERTION	mibig:BGC0002633	DOI:10.1128/aem.02373-21
Nostoc sp. PCC 7120 = FACHB-418 NCBITaxon:103690	SOURCE_ASSERTION	mibig:BGC0002683	DOI:10.1111/j.1529-8817.1976.tb02824.x

Occurrences 7

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
Anabaena NCBITaxon:1163	LOTUS	DOI:10.1021/BI00802A010
Anabaena NCBITaxon:1163	LOTUS	DOI:10.1128/JB.01062-08
Anabaena sp. NCBITaxon:1167	CHEBI	PMID:6806241
Bacillus megaterium NCBITaxon:1404	LOTUS	DOI:10.1021/BI00802A010
Bacillus megaterium NCBITaxon:1404	CHEBI	PMID:4960152
Ralstonia solanacearum NCBITaxon:305	LOTUS	DOI:10.1515/ZNC-1997-7-812
Leptolyngbya NCBITaxon:47251	LOTUS	DOI:10.1128/AEM.02373-21

Biosynthetic gene clusters 2

Accession	Host	Locus evidence	Genome
mibig:BGC0002633	Leptolyngbya sp. PCC 7376 NCBITaxon:111781	CLUSTER_DEMONSTRATED	genbank:CP003946.1
mibig:BGC0002683	Nostoc sp. PCC 7120 = FACHB-418 NCBITaxon:103690	CLUSTER_UNSTATED	genbank:BA000019.2

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

Causal graph — biosynthesis 4 nodes, 3 edges

Leptolyngbya sp. PCC 7376 LidC and LidF IucA/IucC-family synthetases in the heterologously expressed lidA-lidF cassette that produces schizokinen.

Subject	Predicate	Object	Notes	Evidence
LidC IucA/IucC family protein	participates in	Leptolyngbya lidA-lidF schizokinen core assembly	LidC is one of two IucA/IucC family synthetases in the experimentally expressed Leptolyngbya lidA-lidF core cassette; no exact single-enzyme reaction was assigned.	DOI:10.1128/aem.02373-21 https://mibig.secondarymetabolites.org/repository/BGC0002633.2/ https://www.uniprot.org/uniprotkb/K9Q581 reference DOI:10.1128/aem.02373-21 evidence type PRIMARY_EXPERIMENT snippet expression strains harboring the first seven genes (lidA to lidF) notes Wang et al. cloned the Leptolyngbya sp. PCC 7376 siderophore cassette, expressed lidA through lidF in Escherichia coli, and identified the produced siderophore as schizokinen by UPLC-MS/MS and NMR. The paper places LidC and LidF in the core schizokinen cassette but does not assign their individual citrate-acylation order. reference https://mibig.secondarymetabolites.org/repository/BGC0002633.2/ evidence type DATABASE_ASSERTION retrieved on 2026-09-30 notes MIBiG entry version 2 maps BGC0002633 to schizokinen biosynthesis in Leptolyngbya sp. PCC 7376 and lists Lepto7376_4149 / AFY40274.1 and Lepto7376_4153 / AFY40278.1 as IucA/IucC family protein CDS features inside the CP003946.1 locus. reference https://www.uniprot.org/uniprotkb/K9Q581 evidence type DATABASE_ASSERTION retrieved on 2026-09-30 notes UniProtKB:K9Q581 is the unreviewed [Leptolyngbya] sp. PCC 7376 IucA/IucC family protein entry resolved from AFY40274.1 / Lepto7376_4149.
LidF IucA/IucC family protein	participates in	Leptolyngbya lidA-lidF schizokinen core assembly	LidF is one of two IucA/IucC family synthetases in the experimentally expressed Leptolyngbya lidA-lidF core cassette; no exact single-enzyme reaction was assigned.	DOI:10.1128/aem.02373-21 https://mibig.secondarymetabolites.org/repository/BGC0002633.2/ https://www.uniprot.org/uniprotkb/K9Q4J7 reference DOI:10.1128/aem.02373-21 evidence type PRIMARY_EXPERIMENT notes Wang et al. cloned the Leptolyngbya sp. PCC 7376 siderophore cassette, expressed lidA through lidF in Escherichia coli, and identified the produced siderophore as schizokinen by UPLC-MS/MS and NMR. The paper places LidC and LidF in the core schizokinen cassette but does not assign their individual citrate-acylation order. reference https://mibig.secondarymetabolites.org/repository/BGC0002633.2/ evidence type DATABASE_ASSERTION retrieved on 2026-09-30 notes MIBiG entry version 2 maps BGC0002633 to schizokinen biosynthesis in Leptolyngbya sp. PCC 7376 and lists Lepto7376_4149 / AFY40274.1 and Lepto7376_4153 / AFY40278.1 as IucA/IucC family protein CDS features inside the CP003946.1 locus. reference https://www.uniprot.org/uniprotkb/K9Q4J7 evidence type DATABASE_ASSERTION retrieved on 2026-09-30 notes UniProtKB:K9Q4J7 is the unreviewed [Leptolyngbya] sp. PCC 7376 IucA/IucC family protein entry resolved from AFY40278.1 / Lepto7376_4153.
Leptolyngbya lidA-lidF schizokinen core assembly	produces	schizokinen	Heterologous expression of lidA through lidF produced a schizokinen core; the downstream lidG1-lidG5 genes were not required for the schizokinen product detected in Escherichia coli.	DOI:10.1128/aem.02373-21 https://mibig.secondarymetabolites.org/repository/BGC0002633.2/ reference DOI:10.1128/aem.02373-21 evidence type PRIMARY_EXPERIMENT snippet identified via UPLC-MS/MS and NMR as schizokinen notes Wang et al. cloned the Leptolyngbya sp. PCC 7376 siderophore cassette, expressed lidA through lidF in Escherichia coli, and identified the produced siderophore as schizokinen by UPLC-MS/MS and NMR. The paper places LidC and LidF in the core schizokinen cassette but does not assign their individual citrate-acylation order. reference https://mibig.secondarymetabolites.org/repository/BGC0002633.2/ evidence type DATABASE_ASSERTION retrieved on 2026-09-30 notes MIBiG entry version 2 maps BGC0002633 to schizokinen biosynthesis in Leptolyngbya sp. PCC 7376 and lists Lepto7376_4149 / AFY40274.1 and Lepto7376_4153 / AFY40278.1 as IucA/IucC family protein CDS features inside the CP003946.1 locus.

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

Explore across X-Mech

AntibioticMech (schizokinen) ↗ MediaIngredientMech (CHEBI:84582) ↗ TaxonMech: Leptolyngbya sp. PCC 7376 (NCBITaxon:111781) ↗ TaxonMech: Nostoc sp. PCC 7120 = FACHB-418 (NCBITaxon:103690) ↗ PathwayMech (mibig:BGC0002633) ↗ PathwayMech (mibig:BGC0002683) ↗

Open questions 1

shared-structure — This structure is reported by more than one MIBiG entry: BGC0002633, BGC0002683. Confirm they describe the same compound rather than an upstream cross-reference error.

Provenance

Source concept	Source	Version
BGC0002633	MIBIG	2
BGC0002683	MIBIG	2
CHEBI:84582	CHEBI	3-star

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