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CHEBI:7025 - mupirocin

Default Structure
ChEBI IDCHEBI:7025
ChEBI Namemupirocin
Stars
DefinitionAn 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.
Secondary ChEBI IDCHEBI:44038
Last Modified13 January 2020
DownloadsMolfile
FormulaC26H44O9
Net Charge0
Average Mass500.629
Monoisotopic Mass500.29853
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
InChIInChI=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
InChIKeyMINDHVHHQZYEEK-HBBNESRFSA-N
Wikipedia
Roles Classification
Chemical Role:
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Roles:
bacterial metabolite  Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
protein synthesis inhibitor  A compound, usually an anti-bacterial agent or a toxin, which inhibits the synthesis of a protein.
antibacterial drug  A drug used to treat or prevent bacterial infections.
Application:
antibacterial drug  A drug used to treat or prevent bacterial infections.
ChEBI Ontology
Outgoing Relation(s)
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 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)
mupirocin (CHEBI:7025) is a α,β-unsaturated carboxylic ester (CHEBI:51737)
mupirocin (CHEBI:7025) is conjugate acid of mupirocin(1−) (CHEBI:145790)
Incoming Relation(s)
mupirocin(1−) (CHEBI:145790) is conjugate base of mupirocin (CHEBI:7025)
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  Source
mupirocinWHO MedNet
mupirocinaWHO MedNet
mupirocineWHO MedNet
mupirocinumWHO MedNet
Synonym  Source
Pseudomonic acid AChemIDplus
Brand Names  Source
BactrobanChemIDplus
CentanyChemIDplus
Manual XrefsDatabases
1857DrugCentral
D01076KEGG DRUG
DB00410DrugBank
DE2227739Patent
HMDB0014554HMDB
MupirocinWikipedia
US3977943Patent
US4071536Patent
Registry NumbersSources
CAS:12650-69-0KEGG COMPOUND
CAS:12650-69-0ChemIDplus
Citations