fluopsin C

CHEBI:222417 EXACT REVIEWED 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REVIEWED records curator sign-off on identity, structure, filing class and producer claims; DEPRECATED retains a superseded or out-of-scope record.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.

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A copper coordination entity in which copper(2+) is coordinated to two molar equivalents of [methanethioyl(methyl)amino]oxidanide. It is an antibiotic from Pseudomonas aeruginosa.

Structure

Standard InChIKey	PGYZQLIUYISMJD-UHFFFAOYSA-N
SMILES	CN1C=[S][Cu]2([O]1)[O]N(C)C=[S]2
Stereochemistry	fully defined

Filing pathway

Alkaloids — computed by NPClassifier npclassifier.gnps2.org@2026-10-30, which is why it is pinned rather than recomputed.

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
Pseudomonas aeruginosa PAO1 Strain: PAO1 NCBITaxon:208964	BGC_CHARACTERIZED		PMID:34793213 reference PMID:34793213 evidence type PRIMARY_EXPERIMENT notes Genetic deletion and biochemical reconstitution of the flcA-flcE operon (PA3515-PA3519) in Pseudomonas aeruginosa PAO1 demonstrate biosynthesis of the bis(N-methyl-N-hydroxythioformamido)copper(II) chalkophore complex fluopsin C.
Pseudomonas aeruginosa Strain: M18 NCBITaxon:287	AXENIC_CULTURE		PMID:5549384 reference PMID:5549384 evidence type PRIMARY_EXPERIMENT notes Isolation, structural elucidation, and synthesis of thioformin (fluopsin) and its cupric complex YC 73 (fluopsin C) from Pseudomonas sp.

Occurrences 2

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
Pseudomonas fluorescens NCBITaxon:294	CHEBI	PMID:4468081
Pseudomonas aeruginosa NCBITaxon:287	CHEBI	PMID:34793213

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	FlcA-FlcE (PA3515-PA3519 biosynthetic pathway) + spontaneous Cu(II) complexation		CHEBI:17561 + CHEBI:15414 + CHEBI:231919 + CHEBI:29036 → CHEBI:222417	PMID:34793213

Step 1: Biosynthesis of N-methyl-N-hydroxythioformamide (fluopsin) from L-cysteine and S-adenosyl-L-methionine followed by 2:1 coordination of copper(2+) via thiohydroxamate sulfur and oxygen donor atoms to yield fluopsin C.

Mechanism & Biosynthesis Overview

Causal graph — bioactivity 5 nodes, 4 edges

Formation of the bis(thiohydroxamato)copper(II) metallophore fluopsin C from two equivalents of monomeric fluopsin and Cu(II) and its role in bacterial copper detoxification and broad-spectrum antimicrobial activity.

Subject	Predicate	Object	Notes	Evidence
fluopsin	precursor_of	fluopsin C	Two monomeric fluopsin ligands coordinate a single central Cu(II) cation.	PMID:34793213 reference PMID:34793213 evidence type PRIMARY_EXPERIMENT notes Two thiohydroxamate ligands chelate one Cu(II) ion to form fluopsin C.
copper(2+)	incorporated_into	fluopsin C	Divalent copper(2+) is coordinated in square-planar S2O2 geometry within fluopsin C.	PMID:5549384 reference PMID:5549384 evidence type PRIMARY_EXPERIMENT notes Fluopsin C is bis(N-methyl-N-hydroxythioformamide)copper(II).
fluopsin C	enables	copper ion transport	Buffers extracellular copper(2+) and confers copper resistance in Pseudomonas aeruginosa.	PMID:34793213 reference PMID:34793213 evidence type PRIMARY_EXPERIMENT notes Production of fluopsin C is induced by copper and required for wild-type copper resistance.
fluopsin C	chelates	iron(3+)	Exchanges Cu(II) for Fe(III) in ferric-rich media to form the 3:1 complex fluopsin F.	PMID:4927254 reference PMID:4927254 evidence type PRIMARY_EXPERIMENT notes Conversion between Cu(II)-bound fluopsin C and Fe(III)-bound fluopsin F.

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

Molecular targets 2

Target	Target organism	Measurement	Evidence
copper(2+) OTHER BINDS Intramolecular square-planar bis(N-methyl-N-hydroxythioformamide) S,O-chelation of divalent copper(2+); fluopsin C is the native Cu(II)-bound chalkophore/cuprophore complex secreted by Pseudomonas aeruginosa and Pseudomonas fluorescens.			PMID:5549384 PMID:34793213 reference PMID:5549384 evidence type PRIMARY_EXPERIMENT notes Structure elucidation and total synthesis of fluopsin C (antibiotic YC 73) as bis(N-methyl-N-hydroxythioformamide)copper(II) produced by Pseudomonas. reference PMID:34793213 evidence type PRIMARY_EXPERIMENT notes The flcA-flcE operon (PA3515-PA3519) in Pseudomonas aeruginosa directs copper-inducible production of fluopsin C for copper resistance.
iron(3+) OTHER BINDS Transmetallation / metal exchange with ferric iron(3+) yields the tris-chelate complex fluopsin F in iron-rich media.			PMID:4927254 reference PMID:4927254 evidence type PRIMARY_EXPERIMENT notes Preparation and metal exchange of copper-bound YC 73 (fluopsin C) and ferric-bound fluopsin F.

Elsewhere in the fleet

AntibioticMech — CHEBI:222417 (same structure, same inchikey)

Explore across X-Mech

AntibioticMech (fluopsin C) ↗ MediaIngredientMech (CHEBI:222417) ↗ TaxonMech: Pseudomonas aeruginosa PAO1 (NCBITaxon:208964) ↗ TaxonMech: Pseudomonas aeruginosa (NCBITaxon:287) ↗

Provenance

Source concept	Source	Version
CHEBI:222417	CHEBI	3-star

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