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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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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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
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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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
InChI Key MINDHVHHQZYEEK-HBBNESRFSA-N
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)
ChEMBL Ligand CHEMBL719
DrugBank Ligand DB00410
DrugCentral Ligand 1857
GtoPdb PubChem SID 405560357
PubChem CID 446596
RCSB PDB Ligand MRC
Search Google for chemical match using the InChIKey MINDHVHHQZYEEK-HBBNESRFSA-N
Search Google for chemicals with the same backbone MINDHVHHQZYEEK
Search PubMed clinical trials mupirocin
Search PubMed titles mupirocin
Search PubMed titles/abstracts mupirocin
UniChem Compound Search for chemical match using the InChIKey MINDHVHHQZYEEK-HBBNESRFSA-N
UniChem Connectivity Search for chemical match using the InChIKey MINDHVHHQZYEEK-HBBNESRFSA-N