mupirocin   Click here for help

GtoPdb Ligand ID: 10916

Synonyms: Bactroban® | BRL-4910A | BRL-4910F | Centany® | pseudomonic acid
Approved drug PDB Ligand Antimalarial Ligand
mupirocin is an approved drug (FDA (1987), UK (1998))
Compound class: Synthetic organic
Comment: Mupirocin was initially isolated from Pseudomonas fluorescens [1]. It is an unsaturated ester of 9-hydroxynonanoic acid. Functionally, it binds to bacterial isoleucyl-tRNA synthetase and disrupts isoleucine incorporation into bacterial proteins. This is a unique mechanism of action.

Isoleucine utilization has also been shown to be an essential pathway in P. falciparum and a potential target for antimalarial drug discovery [3]. The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 9
Hydrogen bond donors 4
Rotatable bonds 17
Topological polar surface area 146.05
Molecular weight 500.3
XLogP 2.45
No. Lipinski's rules broken 1
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Canonical SMILES OC(=O)CCCCCCCCOC(=O)/C=C(/C[C@@H]1OC[C@@H]([C@H]([C@H]1O)O)C[C@@H]1O[C@H]1[C@H]([C@@H](O)C)C)\C
Isomeric SMILES OC(=O)CCCCCCCCOC(=O)/C=C(/C[C@@H]1OC[C@@H]([C@H]([C@H]1O)O)C[C@@H]1O[C@H]1[C@H]([C@@H](O)C)C)\C
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
Classification Click here for help
Compound class Synthetic organic
Ligand families/groups Antimalarial ligands
Approved drug? Yes (FDA (1987), UK (1998))
WHO Essential Medicine WHO Essential Medicines List (EML) (23rd List, 2023). Access PDF version.
Click to view more information about the WHO Model Lists of Essential Medicines.
IUPAC Name Click here for help
9-[(E)-4-[(2S,3R,4R,5S)-3,4-dihydroxy-5-[[(2S,3S)-3-[(2S,3S)-3-hydroxybutan-2-yl]oxiran-2-yl]methyl]oxan-2-yl]-3-methylbut-2-enoyl]oxynonanoic acid
International Nonproprietary Names Click here for help
INN number INN
5276 mupirocin
Synonyms Click here for help
Bactroban® | BRL-4910A | BRL-4910F | Centany® | pseudomonic acid
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Mupirocin, pseudomonic acid
Other databases
BindingDB Ligand 50290686
CAS Registry No. 12650-69-0 (source: WHO INN record)
DrugBank Ligand DB00410
DrugCentral Ligand 1857
GtoPdb PubChem SID 405560357
PubChem CID 446596
Search Google for chemical match using the InChIKey MINDHVHHQZYEEK-HBBNESRFSA-N
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UniChem Compound Search for chemical match using the InChIKey MINDHVHHQZYEEK-HBBNESRFSA-N
UniChem Connectivity Search for chemical match using the InChIKey MINDHVHHQZYEEK-HBBNESRFSA-N