mupirocin

CHEBI:7025 ·resolve ·ANTIBACTERIAL ·EXACT SEEDED

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

Machine-generated and unreviewed. Identity, structure and cross-references come straight from ChEBI's and CARD's own data; no curator has signed off on this record yet.

Classification

mupirocin-like antibioticARO:3007151

Strictly broader compounds or drug classes this molecule belongs to.

CHEBI:25384 CHEBI:25384
CHEBI:27136 CHEBI:27136
CHEBI:32955 CHEBI:32955
CHEBI:35681 CHEBI:35681
CHEBI:46942 CHEBI:46942
CHEBI:51737 CHEBI:51737
ARO:3007151 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

Equivalent identifiers for this same structure in other resources.

ARO:3000554
cas:12650-69-0
drugbank:DB00410
drugcentral:1857
hmdb:HMDB0014554
kegg.drug:D01076
patent:DE2227739
patent:US3977943
patent:US4071536
wikipedia.en:Mupirocin
chembl:CHEMBL719
pubchem.compound:446596

Activity roles

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

CHEBI:36047 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.)

Mechanism summary

Mode of action: PROTEIN_SYNTHESIS_INHIBITION host shared target — Assigned from ChEBI role CHEBI:48001 (protein synthesis inhibitor). ChEBI asserts the role on the compound. The target it names is one the host has too, so the mechanism is true but is not evidence of selectivity — see mode_of_action_target_scope. Not a curator's mechanistic review.
Clinical status: APPROVED

Resistance mechanisms

4 known routes by which microbes resist this compound, grounded in ARO where CARD models them. Grouped by mechanism type — expand a group to see its determinants.

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.)

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

Provenance

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