fluopsin
CHEBI:231919 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REVIEWED records curator sign-off on identity, structure, filing class and producer claims; DEPRECATED retains a superseded or out-of-scope record.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 thiocarbonyl compound that is ammonia in which the hydrogens are substituted by methyl, hydroxy, and carbonothioyl groups.
Structure
| Standard InChIKey | LSLVHNSGLHQBDX-UHFFFAOYSA-N |
|---|---|
| SMILES | CN(O)C=S |
| Stereochemistry | fully defined |
Filing pathway
Unclassified — computed by NPClassifier npclassifier.gnps2.org@2026-10-30, which is why it is pinned rather than recomputed.
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 |
|---|---|---|---|
| Pseudomonas aeruginosa PAO1 Strain: PAO1 NCBITaxon:208964 |
BGC_CHARACTERIZED | PMID:34793213
|
Occurrences 0
None cited.
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 enzymes) | CHEBI:17561 + CHEBI:15414 → CHEBI:231919 | PMID:34793213 |
Step 1: Conjugation of L-cysteine and fumarate followed by lyase cleavage, N-hydroxylation, and SAM-dependent N-methylation to yield the free thiohydroxamate monomer fluopsin (N-methyl-N-hydroxythioformamide).
Mechanism & Biosynthesis Overview
Causal graph — bioactivity 10 nodes, 9 edges
Copper-inducible biosynthesis of the thiohydroxamate metallophore fluopsin (N-methyl-N-hydroxythioformamide) from L-cysteine via the flcA-flcE (PA3515-PA3519) operon in Pseudomonas spp. and bidentate S,O-chelation of Cu(II) (forming fluopsin C), Fe(III) (forming fluopsin F), and CMM cations Ni(II) and Co(II).
| Subject | Predicate | Object | Notes | Evidence |
|---|---|---|---|---|
| L-cysteine | substrate_of | flcA-flcE (PA3515-PA3519) biosynthetic operon | L-cysteine donates the sulfur and nitrogen atoms of the thiohydroxamate group. | PMID:34793213
|
| S-adenosyl-L-methionine | substrate_of | flcA-flcE (PA3515-PA3519) biosynthetic operon | SAM provides the N-methyl group of N-methyl-N-hydroxythioformamide. | PMID:34793213
|
| flcA-flcE (PA3515-PA3519) biosynthetic operon | synthesizes | fluopsin | Produces the monomeric thiohydroxamate ligand fluopsin. | PMID:34793213
|
| fluopsin | chelates | copper(2+) | Two equivalents of fluopsin coordinate Cu(II) via S,O-donor atoms. | PMID:34793213
|
| copper(2+) | forms_complex | fluopsin C | Yields the neutral bis(thiohydroxamato)copper(II) complex fluopsin C. | PMID:5549384
|
| fluopsin C | regulates | copper ion transport | Protects Pseudomonas aeruginosa against copper toxicity and mediates copper homeostasis. | PMID:34793213
|
| fluopsin | chelates | iron(3+) | Three equivalents of fluopsin coordinate Fe(III) to form tris(thiohydroxamato)iron(III) (fluopsin F). | PMID:4927254
|
| fluopsin | chelates | nickel(2+) | [CMM] In vitro bidentate S,O-coordination of divalent nickel(2+). | PMID:4927254
|
| fluopsin | chelates | cobalt(2+) | [CMM] In vitro bidentate S,O-coordination of cobalt(2+). | PMID:4927254
|
Every edge carries its own citation; an uncited edge is refused by the corpus tests.
Molecular targets 5
| Target | Target organism | Measurement | Evidence |
|---|---|---|---|
| copper(2+) OTHER BINDS Primary physiological copper(2+) chelation via two N-methyl-N-hydroxylthioamide (thiohydroxamate) ligands to form the square-planar bis(N-methyl-N-hydroxythioformamide)copper(II) complex fluopsin C (YC 73); induced under excess copper for detoxification and antimicrobial defense. |
PMID:34793213 |
||
| iron(3+) OTHER BINDS Chelation of ferric iron(3+) in a 3:1 ligand:metal stoichiometry to form the octahedral tris(N-methyl-N-hydroxythioformamide)iron(III) complex fluopsin F in culture broth. |
PMID:4927254 |
||
| nickel(2+) OTHER BINDS [Critical Mineral & Material (CMM)] Square-planar bis-thiohydroxamate coordination of divalent nickel(2+) in vitro (2:1 ligand:Ni(II) complex formed by synthetic complexation with the N-methyl-N-hydroxylthioamide ligand). |
PMID:4927254
|
||
| cobalt(2+) OTHER BINDS [Critical Mineral & Material (CMM)] Coordination of cobalt(2+) by the N-methyl-N-hydroxylthioamide ligand in vitro (secondary non-physiological complexation relative to Cu(II) and Fe(III)). |
PMID:4927254
|
||
| zinc(2+) OTHER BINDS Bidentate S,O-coordination of divalent zinc(2+) by the thiohydroxamate ligand in vitro. |
PMID:4927254
|
Elsewhere in the fleet
- AntibioticMech — CHEBI:231919 (same structure, same inchikey)
Explore across X-Mech
Provenance
| Source concept | Source | Version |
|---|---|---|
| CHEBI:231919 | CHEBI | 3-star |
This page is generated from data/natural_products/unclassified/fluopsin.yaml, which is generated from the committed inventories. Neither is edited by hand.