CHEBI:7025 - mupirocin

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ChEBI Name mupirocin
ChEBI ID CHEBI:7025
Definition 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.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:44038
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Formula C26H44O9
Net Charge 0
Average Mass 500.62220
Monoisotopic Mass 500.299
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
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
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): bacterial metabolite
Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
antibacterial drug
A drug used to treat or prevent bacterial infections.
protein synthesis inhibitor
A compound, usually an anti-bacterial agent or a toxin, which inhibits the synthesis of a protein.
Application(s): antibacterial drug
A drug used to treat or prevent bacterial infections.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing mupirocin (CHEBI:7025) has role antibacterial drug (CHEBI:36047)
mupirocin (CHEBI:7025) has role bacterial metabolite (CHEBI:76969)
mupirocin (CHEBI:7025) has role protein synthesis inhibitor (CHEBI:48001)
mupirocin (CHEBI:7025) is a α,β-unsaturated carboxylic ester (CHEBI:51737)
mupirocin (CHEBI:7025) is a epoxide (CHEBI:32955)
mupirocin (CHEBI:7025) is a monocarboxylic acid (CHEBI:25384)
mupirocin (CHEBI:7025) is a oxanes (CHEBI:46942)
mupirocin (CHEBI:7025) is a secondary alcohol (CHEBI:35681)
mupirocin (CHEBI:7025) is a triol (CHEBI:27136)
IUPAC Name
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
INNs Sources
mupirocin WHO MedNet
mupirocina WHO MedNet
mupirocine WHO MedNet
mupirocinum WHO MedNet
Synonym Source
Pseudomonic acid A ChemIDplus
Brand Names Sources
Bactroban ChemIDplus
Centany ChemIDplus
Manual Xrefs Databases
1857 DrugCentral
D01076 KEGG DRUG
DB00410 DrugBank
DE2227739 Patent
HMDB0014554 HMDB
Mupirocin Wikipedia
US3977943 Patent
US4071536 Patent
View more database links
Registry Numbers Types Sources
12650-69-0 CAS Registry Number KEGG COMPOUND
12650-69-0 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
22500807 PubMed citation Europe PMC
23337107 PubMed citation Europe PMC
23535880 PubMed citation Europe PMC
23543635 PubMed citation Europe PMC
24625190 PubMed citation Europe PMC
3101012 PubMed citation Europe PMC
Last Modified
22 February 2017