MUPIROCIN

/static/temp/default.svg

Search structure


Trade Names	BACTROBAN CENTANY MUPIROCIN
Synonyms	BRL 4910A BRL-4910A Bactoderm Bactroban Centany Mupirocin NSC-759182 Pseudomonic acid Trans-pseudomonic acid Turixin
Status
Molecule Category	Free-form
ATC	D06AX09 R01AX06
UNII	D0GX863OA5
EPA CompTox	DTXSID0046438


Active Pharmaceutical Ingredients Bioactive chemicals	Exact Similarity SubStructure	Threshold (%) >= 70

Structure


InChI Key	MINDHVHHQZYEEK-HBBNESRFSA-N
Smiles	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
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

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C26H44O9
Molecular Weight	500.63
AlogP	2.59
Hydrogen Bond Acceptor	8.0
Hydrogen Bond Donor	4.0
Number of Rotational Bond	16.0
Polar Surface Area	146.05
Molecular species	ACID
Aromatic Rings	0.0
Heavy Atoms	35.0

Bioactivity

Mechanism of Action	Action	Reference
Isoleucyl-tRNA synthetase inhibitor	INHIBITOR	DailyMed

Targets	EC50(nM)	IC50(nM)	Kd(nM)	Ki(nM)	Inhibition(%)
Enzyme Ligase	-	1	-	60-15000	-

Assay Description	Organism	Bioactivity	Reference
Compound was evaluated for inhibitory activity against Isoleucyl-tRNA synthetase	Escherichia coli	0.8 nM
Inhibition concentration against Isoleucyl-tRNA synthetase from Staphylococcus aureus NCTC 6571	Staphylococcus aureus	0.00085 ug.mL-1
Inhibitory activity against isoleucyl-tRNA synthetase (IRS) of Staphylococcus aureus 11481	Staphylococcus aureus	0.14 ug.mL-1
Inhibitory activity against isoleucyl-tRNA synthetase (IRS) of Staphylococcus aureus C 7	Staphylococcus aureus	20.0 ug.mL-1
Inhibitory activity against isoleucyl-tRNA synthetase (IRS) of Staphylococcus aureus NCTC 6571	Staphylococcus aureus	0.0008 ug.mL-1
PUBCHEM_BIOASSAY: Luminescence Microorganism-Based Dose Response HTS to Identify Compounds Cytotoxic to Streptococcus. (Class of assay: confirmatory) [Related pubchem assays: 1900 (Counter Screen), 1677 (Project Summary), 1902 (Retest at Dose), 1662 (Primary HTS)]	Streptococcus	60.0 nM
PUBCHEM_BIOASSAY: Luminescence Microorganism-Based Dose Confirmation HTS to Identify Compounds Cytotoxic to SK(-)GAS Group A Streptococcus. (Class of assay: confirmatory) [Related pubchem assays: 1677 (Project Summary), 1662 (Primary HTS)]	Streptococcus	60.0 nM
PUBCHEM_BIOASSAY: Luminescence Microorganism-Based Dose Confirmation HTS to Identify Inhibitors of Streptokinase Promotor Activity. (Class of assay: confirmatory) [Related pubchem assays: 1677 (Project Summary), 1662 (Primary HTS)]	Streptococcus pyogenes M1 GAS	60.0 nM
PUBCHEM_BIOASSAY: Absorbance Microorganism-Based Dose Response HTS to Identify Inhibitors of Streptokinase Expression. (Class of assay: confirmatory) [Related pubchem assays: 1677 (Project Summary), 1902 (Retest at Dose), 1900 (Counter Screen), 1662 (Primary HTS)]	Streptococcus pyogenes M1 GAS	423.0 nM
Competitive inhibition of Escherichia coli Isoleucyl-tRNA synthetase	Escherichia coli	2.5 nM
Inhibition of Spinacia oleracea (spinach) chloroplast isoleucyl tRNA synthetase at 1 uM	Spinacia oleracea	75.0 %
Inhibition of recombinant Thermus thermophilus HB8 wild type IleRS assessed as suppression of L-[14C]isoleucyl-tRNA(Ile) formation	Thermus thermophilus HB8	250.0 nM
Inhibition of recombinant Thermus thermophilus HB8 IleRS L583F mutant assessed as suppression of L-[14C]isoleucyl-tRNA(Ile) formation	Thermus thermophilus HB8	60.0 nM
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of Caco-2 cells at 10 uM after 48 hours by high content imaging	Homo sapiens	26.23 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	13.89 %		SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	14.73 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	0.07 %		Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	0.25 %		Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	0.07 %		Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	0.25 %

Related Entries

Cross References

Resources	Reference
ChEBI	7025
ChEMBL	CHEMBL719
DrugBank	DB00410
DrugCentral	1857
FDA SRS	D0GX863OA5
Human Metabolome Database	HMDB0014554
Guide to Pharmacology	10916
KEGG	C11758
PDB	MRC
PharmGKB	PA164764568
PubChem	446596
SureChEMBL	SCHEMBL3291
ZINC	ZINC000004102194

CONTENTS

PREMIER has received funding from the Innovative Medicines Initiative 2 Joint Undertaking (JU) under grant agreement No 875508. The JU receives support from the EU’s Horizon 2020 research and innovation programme and the European Federation of Pharmaceutical Industries and Associations (EFPIA). The views reflect only the authors’ perspective and the JU is not responsible for any use that may be made of the information this manuscript contains.

Elements of the website have been developed under projects PREMIER and the Biocenter Finland Drug Discovery and Chemical Biology network. CSC-IT is thanked for providing computational resources. Content of the website is provided without guarantee for correctness. Data has been collected and integrated from multiple public sources, for the largest: FDA, HUGO Gene Nomenclature Committee, ChEMBL, IUPHAR/BPS guide to pharmacology, Reactome, UniProt, and Ensembl. Credit is given to Ensembl for collecting species images (provided under public domain licences such as Wikimedia and NHGRI).