mupirocin
CHEBI:7025 EXACT SEEDED antibacterial
An α,β-unsaturated ester resulting from the formal condensation of the alcoholic hydroxy group of 9-hydroxynonanoic acid with the carboxy group of (2E)-4-[(2S)-tetrahydro-2H-pyran-2-yl]-3-methylbut-2-enoic acid in which the tetrahydropyranyl ring is substituted at positions 3 and 4 by hydroxy groups and at position 5 by a {(2S,3S)-3-[(2S,3S)-3-hydroxybutan-2-yl]oxiran-2-yl}methyl group. Originally isolated from the Gram-negative bacterium Pseudomonas fluorescens, it is used as a topical antibiotic for the treatment of Gram-positive bacterial infections.
Structure
| Standard InChIKey | MINDHVHHQZYEEK-HBBNESRFSA-N |
|---|---|
| SMILES | C[C@H](O)[C@H](C)[C@@H]1O[C@H]1C[C@H]1CO[C@@H](C\C(C)=C\C(=O)OCCCCCCCCC(O)=O)[C@H](O)[C@@H]1O |
| Stereochemistry | fully defined |
| Cross-references | npatlas:NPA06173 |
Filing pathway
Polyketides — 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 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 |
|---|---|---|---|
| Pseudomonas fluorescens NCBITaxon:294 |
BGC_CHARACTERIZED | mibig:BGC0000182 | PMID:11495990 |
Occurrences 5
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 |
LOTUS | DOI:10.1039/C39740000847 |
| Pseudomonas fluorescens NCBITaxon:294 |
LOTUS | DOI:10.1039/P19890000207 |
| Pseudomonas fluorescens NCBITaxon:294 |
LOTUS | DOI:10.1099/00221287-147-8-2127 |
| Pseudomonas fluorescens NCBITaxon:294 |
LOTUS | DOI:10.1111/J.1574-6968.1989.TB03082.X |
| Pseudomonas fluorescens NCBITaxon:294 |
LOTUS | DOI:10.1128/AAC.27.4.495 |
Biosynthetic gene clusters 1
| Accession | Host | Locus evidence | Genome |
|---|---|---|---|
| mibig:BGC0000182 | Pseudomonas fluorescens NCBITaxon:294 |
CLUSTER_DEMONSTRATED | genbank:AF318063.3 |
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.
Elsewhere in the fleet
- AntibioticMech — CHEBI:7025 (same structure, same inchikey)
Open questions 1
name-disagreement — ChEBI calls this structure 'mupirocin' and MIBiG calls it 'pseudomonic acid A'. They share a Standard InChIKey, so if the names denote different compounds then one upstream record has the wrong structure. Check which.
Provenance
| Source concept | Source | Version |
|---|---|---|
| BGC0000182 | MIBIG | 5 |
| CHEBI:7025 | CHEBI | 3-star |
This page is generated from data/natural_products/polyketides/mupirocin.yaml, which is generated from the committed inventories. Neither is edited by hand.