Mupirocin (CED0003163)

Record Information

Version

1.0

Creation Date

2016-05-22 05:44:35 UTC

Update Date

2026-08-22 07:02:37 UTC

Accession Number

CHEM018993

Identification

Common Name

Mupirocin

Class

Small Molecule

Description

Mupirocin is a compound with the chemical formula C26H44O9. Mupirocin belongs to the fatty acids and conjugates, a subclass of fatty acyls within the organic compounds. With an average molecular weight of 500.62 g/mol, Mupirocin is a heavy molecule. Biologically, it serves as an antibacterial agent (PMC11508006) and acts as an inhibitor of Isoleucine--tRNA ligase (ileS). The compound is found in or released from 11 recorded sources. These include healthcare, pharmaceuticals and veterinary products such as nasal preparations and antibiotics; household cleaning and consumer products, specifically pipe accessories, tobacco pipes, other smoking requisites, and non electric simulated smoking devices; food, food processing and cookware, including processing meats; and electrical and electronic equipment, such as auxiliary devices, antennas, video games, and television systems. Recorded exposure routes for Mupirocin are topical and nasal.

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Bactroban	ChEBI
Centany	ChEBI
Mupirocina	ChEBI
Mupirocine	ChEBI
Mupirocinum	ChEBI
Pseudomonic acid a	ChEBI
Pseudomonate a	Generator
MUP	HMDB
MRC	HMDB
Pseudomonic acid	HMDB
BRL 4910a	HMDB
Mupirocin, 14C-labeled	HMDB
Mupirocin, calcium salt (2:1), dihydrate	HMDB
14C-Labeled mupirocin	HMDB
BRL-4910a	HMDB
Mupirocin, 14C labeled	HMDB
Mupirocin, lithium salt	HMDB
Acid, pseudomonic	HMDB
Mupirocin, calcium salt (2:1)	HMDB
Mupirocin, sodium salt	HMDB
Mupirocin calcium	HMDB

Chemical Formula

C₂₆H₄₄O₉

Average Molecular Mass

500.622 g/mol

Monoisotopic Mass

500.299 g/mol

CAS Registry Number

12650-69-0

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}oxan-2-yl]-3-methylbut-2-enoyl]oxy}nonanoic acid

Traditional Name

mupirocin

SMILES

C[C@H](O)[C@H](C)[C@@H]1O[C@H]1C[C@H]1CO[C@@H](C\C(C)=C\C(=O)OCCCCCCCCC(O)=O)[C@H](O)[C@@H]1O

InChI Identifier

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

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Medium-chain fatty acids

Alternative Parents

Substituents

Medium-chain fatty acid
Branched fatty acid
Epoxy fatty acid
Fatty acid ester
Heterocyclic fatty acid
Hydroxy fatty acid
Dicarboxylic acid or derivatives
Oxane
Monosaccharide
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Carboxylic acid ester
Secondary alcohol
Ether
Oxirane
Dialkyl ether
Carboxylic acid
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Carbonyl group
Alcohol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organooxygen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

monocarboxylic acid (CHEBI:7025 )
secondary alcohol (CHEBI:7025 )
epoxide (CHEBI:7025 )
triol (CHEBI:7025 )
alpha,beta-unsaturated carboxylic ester (CHEBI:7025 )
oxanes (CHEBI:7025 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

Not Available

Biological Roles

antibacterial agent

Chemical Roles

Not Available

Organoleptic Effects

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.026 g/L	ALOGPS
logP	2.25	ALOGPS
logP	2.45	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	4.83	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	146.05 Å²	ChemAxon
Rotatable Bond Count	17	ChemAxon
Refractivity	129.39 m³·mol⁻¹	ChemAxon
Polarizability	55.5 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-0fc1-2972400000-21f057ea2a2e95898b9d	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-00di-4966726000-06f4a51b9c0619130ac4	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-056r-1976100000-dfa28e3b7efa7b734a99	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0bwa-3920000000-b910c0ca6dcc91904891	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-056r-1976100000-dfa28e3b7efa7b734a99	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0bwa-3920000000-b910c0ca6dcc91904891	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-001i-1342920000-677def34a6e414632f7e	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0670-6981300000-69aa4a4ddd0866e13409	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0zgi-7920100000-472a053832ce780dd335	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0002-0227900000-2b3bd45c30c76c00ada4	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0kka-9776600000-a91ac251679e309216a5	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0kml-9840000000-4c1976a6372a21fd11fd	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-052k-0100900000-2ba1125d17b9a119cec1	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-000i-2132900000-b2848b38bb227b2c50ba	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-052n-4126900000-a6fe8de917ce81221d01	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0fus-2126930000-8ef8418ebf22e9aa7d14	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-015d-9620200000-8cb94d45ef1676428b42	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4l-9600000000-177c92b81937ff998d8e	Not Available	View Spectrum

Toxicity Profile

Mechanism of Toxicity

Not Available

Carcinogenicity (IARC Classification)

Not Available

Minimum Risk Level

Not Available

Symptoms

Not Available

Treatment

Not Available

Toxicity Values

Toxicity Value	Unit	Value Range	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Reference
5730.0	Log mg/kg	[3200:10000]	Rat	LD50	oral	predicted	Not Available

Health Effects

Health Effect	Relationship	Direction	Reference

Exposure Sources

Source ID	Source	Sector	Reference
306	Antibiotics	Healthcare, pharmaceuticals & veterinary products	Not Available
389	Nasal preparations	Healthcare, pharmaceuticals & veterinary products	Not Available
506	Antennas	Electrical & Electronic Equipment	Not Available
507	Auxiliary Devices	Electrical & Electronic Equipment	Not Available
537	Television Systems	Electrical & Electronic Equipment	Not Available
539	Video Games	Electrical & Electronic Equipment	Not Available
552	Processing Meats	Food, food processing & cookware	Not Available
559	Non Electric Simulated Smoking Devices	Household cleaning & consumer products	Not Available
560	Other Smoking Requisites	Household cleaning & consumer products	Not Available
562	Pipe Accessories	Household cleaning & consumer products	Not Available
566	Tobacco Pipes	Household cleaning & consumer products	Not Available
578	Making Cigars	Industrial manufacturing & chemical processing	Not Available
616	Face Mask Cosmetics	Personal care & cosmetics	Not Available
631	Anthraquinone Dyes	Textiles, leather & furnishings	Not Available
633	Azo Dyes	Textiles, leather & furnishings	Not Available
643	Headwear	Textiles, leather & furnishings	Not Available

Pathways

1 pathway

Mupirocin Drug Metabolism Action Pathway

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Isoleucine--tRNA ligase	P56690	Thermus thermophilus (strain HB8 / ATCC 27634 / DSM 579)	Predicted (SEA)	0.0778492
Click to view 3D structure	Isoleucine--tRNA ligase	P00956	Escherichia coli K-12	Predicted (SEA)	0.155698
Click to view 3D structure	Isoleucine--tRNA ligase, cytoplasmic	P41252	Humans	Predicted (SEA)	0.856341
Click to view 3D structure	Streptokinase A	P10520	Streptococcus pyogenes serotype M1	Predicted (SEA)	152.818
Click to view 3D structure	Solute carrier organic anion transporter family member 2B1	Q9JHI3	Rattus norvegicus	Predicted (SEA)	9.73115
Click to view 3D structure	Nuclear receptor subfamily 4 group A member 2	Q07917	Rattus norvegicus	Predicted (SEA)	13.7793
Click to view 3D structure	Prostacyclin receptor	P43119	Humans	Predicted (SEA)	496.834
Click to view 3D structure	Prostaglandin F2-alpha receptor	P43088	Humans	Predicted (SEA)	503.295
Click to view 3D structure	Prostaglandin E2 receptor EP1 subtype	P35375	Mus musculus	Predicted (SEA)	251.453
Click to view 3D structure	Prostaglandin E2 receptor EP3 subtype	P30557	Mus musculus	Predicted (SEA)	337.009
Click to view 3D structure	Prostaglandin E2 receptor EP4 subtype	P32240	Mus musculus	Predicted (SEA)	367.682
Click to view 3D structure	Prostaglandin E2 receptor EP2 subtype	Q62053	Mus musculus	Predicted (SEA)	211.594
Click to view 3D structure	Prostaglandin E2 receptor EP3 subtype	P43115	Humans	Predicted (SEA)	1153.02
Click to view 3D structure	Prostaglandin E2 receptor EP2 subtype	P43116	Humans	Predicted (SEA)	1134.34
Click to view 3D structure	Prostaglandin E2 receptor EP4 subtype	P35408	Humans	Predicted (SEA)	1224.57
Click to view 3D structure	Prostaglandin E2 receptor EP1 subtype	P34995	Humans	Predicted (SEA)	1430.48
Click to view 3D structure	Peroxisome proliferator-activated receptor alpha	Q07869	Humans	Predicted (SEA)	2321.62
Click to view 3D structure	Peroxisome proliferator-activated receptor delta	Q03181	Humans	Predicted (SEA)	1837.71
Click to view 3D structure	Tyrosine-protein phosphatase non-receptor type 1	P18031	Humans	Predicted (SEA)	1780.18
Click to view 3D structure	Putative inactive group IIC secretory phospholipase A2	Q5R387	Humans	Predicted (SEA)	48.5779
Click to view 3D structure	Peroxisome proliferator-activated receptor gamma	P37231	Humans	Predicted (SEA)	3188.7
Click to view 3D structure	Solute carrier organic anion transporter family member 2A1	Q9EPT5	Mus musculus	Predicted (SEA)	16.8933
Click to view 3D structure	Thromboxane A2 receptor	P21731	Humans	Predicted (SEA)	2052.03
Click to view 3D structure	Cytosolic phospholipase A2	A4IFJ5	Bos taurus	Predicted (SEA)	162.549
Click to view 3D structure	P-selectin	Q01102	Mus musculus	Predicted (SEA)	29.0378