mupirocin

CHEBI:7025 ·resolve ·ANTIBACTERIAL ·EXACT REVIEWED

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. — ChEBI

Classification

mupirocin-like antibioticARO:3007151

Strictly broader compounds or drug classes this molecule belongs to.

Label unavailable CHEBI:25384
Label unavailable CHEBI:27136
Label unavailable CHEBI:32955
Label unavailable CHEBI:35681
Label unavailable CHEBI:46942
Label unavailable CHEBI:51737
mupirocin-like antibiotic ARO:3007151

Chemical structure

Computed structure properties
Molecular formula	C26H44O9
Charge	0
Average mass	500.629 Da
Monoisotopic mass	500.29853 Da
Source	ChEBI
InChIKey	MINDHVHHQZYEEK-HBBNESRFSA-N

SMILES

[H][C@@]1([C@@H](C)[C@H](C)O)O[C@@]1([H])C[C@H]1CO[C@@H](C/C(C)=C/C(=O)OCCCCCCCCC(=O)O)[C@H](O)[C@@H]1O

InChI

InChI=1S/C26H44O9/c1-16(13-23(30)33-11-9-7-5-4-6-8-10-22(28)29)12-20-25(32)24(31)19(15-34-20)14-21-26(35-21)17(2)18(3)27/h13,17-21,24-27,31-32H,4-12,14-15H2,1-3H3,(H,28,29)/b16-13+/t17-,18-,19-,20-,21-,24+,25-,26-/m0/s1

Also called

Bactroban (BRAND_NAME)— chebi
Centany (BRAND_NAME)— chebi
mupirocina (INN)— chebi
mupirocine (INN)— chebi
mupirocinum (INN)— chebi
9-({(2E)-4-[(2S,3R,4R,5S)-3,4-dihydroxy-5-({(2S,3S)-3-[(2S,3S)-3-hydroxybutan-2-yl]oxiran-2-yl}methyl)tetrahydro-2H-pyran-2-yl]-3-methylbut-2-enoyl}oxy)nonanoic acid (EXACT_SYNONYM)— chebi
Pseudomonic acid A (EXACT_SYNONYM)— chebi
pseudomonic acid (EXACT_SYNONYM)— aro

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.

Drug registries

Identifiers that name a drug rather than a structure. One of these can cover a parent compound, its salts and its stereoisomers, which this corpus keeps as separate records, so it is not an equivalence of structure.

Patents and articles

Documents about this compound. A patent covers a class and an article covers a topic; neither identifies a structure.

Activity roles

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

antibacterial drug CHEBI:36047

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
ARO	`ARO:3000554`	mupirocin	`antibioticmech:aro-3b020d3551`	2026-08-30
CHEBI	`CHEBI:7025`	mupirocin	`antibioticmech:chebi-47d25852a8`	2026-08-30

Molecular targets

The molecular entity or process this compound acts on. Each target carries evidence — this is a mechanistic claim, not a classification.

antibiotic sensitive Isoleucyl-tRNA transferase PROTEIN DIRECT_BINDING_TARGET

ARO:3000732

CARD/ARO database assertion; target organism, strain, and assay are not specified. Isoleucyl-tRNA synthetase is asserted as the competitive target. Evidence status: PRIMARY_EVIDENCE_NEEDED. Source: CARD_ARO 2026-08-30 (retrieved 2026-08-30).

ARO:3000732 (CARD/ARO asserts targeted_by_antibiotic ARO:3000554 (mupirocin); database assertion, not a primary citation.)

isoleucyl-tRNA synthetase-tRNA(Ile) complex PROTEIN_COMPLEX DIRECT_BINDING_TARGET

A 2.2-angstrom S. aureus IleRS-tRNA(Ile)-mupirocin crystal structure directly observed the antibiotic-bound aminoacyl-tRNA-synthetase complex. Evidence status: PRIMARY_EVIDENCE. Source: PRIMARY_LITERATURE 1999-08 (retrieved 2026-09-02).

Staphylococcus aureus NCBITaxon:1280

Organism-specific examples
Protein	Gene	Organism	Entry
Isoleucine--tRNA ligase `UniProtKB:P41972` Staphylococcus aureus isoleucyl-tRNA synthetase catalytic component crystallized with tRNA(Ile) and mupirocin at the Rossmann-fold active site (PMID:10446055, PDB 1QU2).	ileS	Staphylococcus aureus `NCBITaxon:1280`	REVIEWED

PMID:10446055 (Primary mupirocin-bound S. aureus IleRS-tRNA(Ile) structure.)

Mechanism summary

Mode of action: PROTEIN_SYNTHESIS_INHIBITION host shared target — CURATOR: PMID:10446055 resolved mupirocin in a 2.2-angstrom Staphylococcus aureus isoleucyl-tRNA synthetase (IleRS)-tRNA(Ile) complex. The structure directly supports inhibition of IleRS and hence isoleucyl-tRNA production; the paper focused on tRNA editing geometry rather than reporting an enzyme inhibition constant.
Clinical status: APPROVED

Resistance mechanisms

4 source-backed resistance determinants or associations, with ARO grounding where reported. Grouped by reported mechanism type.

ANTIBIOTIC_TARGET_ALTERATION 4

ANTIBIOTIC_TARGET_ALTERATION
Determinant	ARO ID	Organism	Gene families	Evidence
Bifidobacterium bifidum ileS conferring resistance to mupirocin	ARO:3003730	not organism-specific	—	ARO:3003730 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000554 (mupirocin); database assertion, not a primary citation.)
Staphylococcus aureus ileS with mutation conferring resistance to mupirocin	ARO:3003729	not organism-specific	—	ARO:3003729 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000554 (mupirocin); database assertion, not a primary citation.)
Staphylococcus aureus mupA conferring resistance to mupirocin	ARO:3000521	not organism-specific	—	ARO:3000521 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000554 (mupirocin); database assertion, not a primary citation.)
Staphylococcus aureus mupB conferring resistance to mupirocin	ARO:3000510	not organism-specific	—	ARO:3000510 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000554 (mupirocin); database assertion, not a primary citation.)

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
Pseudomonas fluorescens NCBITaxon:294	BGC0000182	Gene expression correlated with compound production; Knock-out studies compound specific	MIBIG 4.0.1 (entry 5)	questionable	MIBiG active entry; compound 'pseudomonic acid A' joined by exact Standard InChIKey.	PMID:11495990 (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.)

Record-level evidence

PMID:10446055 (Primary exact-mupirocin IleRS-tRNA(Ile) cocrystal study.)

Curation history

SEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Seeded from data/raw/ inventories (ARO, 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 2026-08-31 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-08-31 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-08-31 · seed_from_sources
Re-seeded from updated data/raw/ inventories
REVIEWED 2026-09-03 · codex · LLM-assisted
Verified exact ChEBI/CARD identity, structure, antibiotic role, class, FDA provenance, and retained CARD target/resistance assertions; curator-confirmed protein-synthesis inhibition and added the directly bound IleRS-tRNA complex.
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
RESEEDED_FROM_SOURCES 2026-09-10 · seed_from_sources
Re-seeded from updated data/raw/ inventories
CURATED_UNIPROT_PROTEIN_EXAMPLES 2026-10-18 · antigravity · LLM-assisted
Added curated Staphylococcus aureus IleS (P41972) UniProtKB protein example on the PRIMARY_LITERATURE isoleucyl-tRNA synthetase-tRNA(Ile) complex molecular target.

Provenance

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

Explore across X-Mech: MediaIngredientMech (mupirocin) · CultureMech · NaturalProductMech · PathwayMech · TraitMech · TaxonMech (Pseudomonas fluorescens)