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Compound Detail

CHEMBL719

MUPIROCIN
💊 Approved Drug
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💊 Approved Drug
C/C(=C\C(=O)OCCCCCCCCC(=O)O)C[C@@H]1OC[C@H](C[C@@H]2O[C@H]2[C@@H](C)[C@H](C)O)[C@@H](O)[C@H]1O

Basic Information

ChEMBL ID CHEMBL719
Name MUPIROCIN
Phase Approved
Structure Type MOL
InChI Key MINDHVHHQZYEEK-HBBNESRFSA-N
Therapeutic ✓ Yes

Known Names

Bactoderm Bactroban BRL 4910A BRL-4910A Centany Mupirocin Mupirocina Mupirocine NSC-759182 Pseudomonic acid Trans-pseudomonic acid Turixin
5
Targets
14
Activities
3
Assay Types
0
PK Parameters
20
Publications
12
Known Names
12
Indications
2
Mechanisms

Molecular Properties

500.6
MW (Da)
2.59
ALogP
8
HBA
4
HBD
146.1
PSA (Ų)
0.11
QED
1
Ro5 Violations
16
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1987
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Topical

Flags

Natural Product
USAN Stem -rocin
USAN Year 1986

Extended Properties

Molecular Formula C26H44O9
MW 500.63
Aromatic Rings 0
Heavy Atoms 35
NP-Likeness 1.70

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Isoleucyl-tRNA synthetase inhibitor INHIBITOR Isoleucine--tRNA ligase
Isoleucyl-tRNA synthetase inhibitor INHIBITOR Isoleucine--tRNA ligase

Indications

Impetigo Nasal Obstruction Epistaxis Infections Staphylococcal Infections Telangiectasia, Hereditary Hemorrhagic Cystic Fibrosis Hemangioma Radiodermatitis Sinusitis Bacterial Infections Osteomyelitis

ATC Classification

D06AX09
mupirocin
Level 1: DERMATOLOGICALS
Level 2: ANTIBIOTICS AND CHEMOTHERAPEUTICS FOR DERMATOLOGICAL USE
R01AX06
mupirocin
Level 1: RESPIRATORY SYSTEM
Level 2: NASAL PREPARATIONS

Activity Summary

IC50 7 meas. best 9.1
Ki 6 meas. best 8.6
EC50 1 meas. best 6.37

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Isoleucine--tRNA ligase, cytoplasmic
CHEMBL3235
IC50 9.1 9.1 0.8 1
Isoleucine--tRNA ligase
CHEMBL3657
Ki 8.6 8.6 2.5 1
Isoleucine--tRNA ligase
CHEMBL3879837
Ki 7.22 5.968 60.0 5
Streptokinase A
CHEMBL1293228
EC50 6.37 6.37 423.0 1
Unchecked
CHEMBL612545
IC50 5.01 4.8167 9670.0 6

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Isoleucine--tRNA ligase, cytoplasmic IC50 = 0.8 nM 9.1 Compound was evaluated for inhibitory activity against Isoleucyl-tRNA synthetase -
Isoleucine--tRNA ligase Ki = 2.5 nM 8.6 Competitive inhibition of Escherichia coli Isoleucyl-tRNA synthetase 21968372
Isoleucine--tRNA ligase Ki = 60.0 nM 7.22 Inhibition of recombinant Thermus thermophilus HB8 IleRS L583F mutant assessed a... -
Isoleucine--tRNA ligase Ki = 250.0 nM 6.6 Inhibition of recombinant Thermus thermophilus HB8 wild type IleRS assessed as s... -
Streptokinase A EC50 = 423.0 nM 6.37 PUBCHEM_BIOASSAY: Absorbance Microorganism-Based Dose Response HTS to Identify I... -
Isoleucine--tRNA ligase Ki = 2310.0 nM 5.64 Inhibition of recombinant Thermus thermophilus HB8 IleRS H581L/L583H double muta... -
Isoleucine--tRNA ligase Ki = 2730.0 nM 5.56 Inhibition of recombinant Thermus thermophilus HB8 IleRS H581N/L583F double muta... -
Unchecked IC50 = 9670.0 nM 5.01 PUBCHEM_BIOASSAY: A Counter Screen to identiry small molecule screen for inhibit... -
Unchecked IC50 = 10460.0 nM 4.98 PUBCHEM_BIOASSAY: A small molecule screen for inhibitors of the PhoP region in S... -
Unchecked IC50 = 13080.0 nM 4.88 PUBCHEM_BIOASSAY: A small molecule screen for inhibitors of the PhoP region in S... -
Unchecked IC50 = 14100.0 nM 4.85 PUBCHEM_BIOASSAY: A screen for inhibitors of the PhoP region in Salmonella Typhi... -
Isoleucine--tRNA ligase Ki = 15000.0 nM 4.82 Inhibition of recombinant Thermus thermophilus HB8 IleRS H581S/L583I double muta... -
Unchecked IC50 = 17507.0 nM 4.76 PUBCHEM_BIOASSAY: A screen for inhibitors of the PhoP region in Salmonella Typhi... -
Unchecked IC50 = 38410.0 nM 4.42 PUBCHEM_BIOASSAY: A counter screen for small molecule screen for inhibitors of t... -

Literature References

PubMed DOI Target Context # Activities
25151577 10.1016/j.ejmech.2014.07.106 Staphylococcus aureus 29
16472241 10.2174/1570163043334794 Hepatotoxicity 18
19581456 10.1128/aac.00457-09 Staphylococcus aureus 18
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
18591267 10.1128/aac.00405-08 Escherichia coli 12
17404009 10.1128/aac.01066-06 Staphylococcus aureus 11
18725451 10.1128/aac.00399-08 Staphylococcus aureus 9
18725451 10.1128/aac.00399-08 NON-PROTEIN TARGET 9
20713669 10.1128/aac.00064-10 Staphylococcus aureus 8
18838584 10.1128/aac.00915-08 Staphylococcus aureus 7
18403059 10.1016/j.ejmech.2008.02.021 Staphylococcus aureus 7
17724154 10.1128/aac.00846-07 Staphylococcus aureus 6
18725451 10.1128/aac.00399-08 Staphylococcus 6
18591267 10.1128/aac.00405-08 Klebsiella pneumoniae 6
18591267 10.1128/aac.00405-08 Enterobacter cloacae 6
31265289 10.1021/acs.jmedchem.9b00616 Staphylococcus aureus 5
36394909 10.1021/acs.jmedchem.2c01496 Staphylococcus aureus 5
- 10.1039/C6MD00274A Isoleucine--tRNA ligase 5
8784459 10.1021/jm950882q Staphylococcus aureus 4
20479195 10.1128/aac.01439-09 Escherichia coli 4

Data from ChEMBL 36 via Core Engine