Mupirocin (CHEM018993)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 05:44:35 UTC
Update Date2016-11-09 01:15:54 UTC
Accession NumberCHEM018993
Identification
Common NameMupirocin
ClassSmall Molecule
DescriptionAn alpha,beta-unsaturated ester resulting from the formal condensation of the alcoholic hydroxy group of 9-hydroxynonanoic acid with the carboxy group of (2E)-4-[(2S)-tetrahydro-2H-pyran-2-yl]-3-methylbut-2-enoic acid in which the tetrahydropyranyl ring is substituted at positions 3 and 4 by hydroxy groups and at position 5 by a {(2S,3S)-3-[(2S,3S)-3-hydroxybutan-2-yl]oxiran-2-yl}methyl group. Originally isolated from the Gram-negative bacterium Pseudomonas fluorescens, it is used as a topical antibiotic for the treatment of Gram-positive bacterial infections.
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
BactrobanChEBI
CentanyChEBI
MupirocinaChEBI
MupirocineChEBI
MupirocinumChEBI
Pseudomonic acid aChEBI
Pseudomonate aGenerator
MUPHMDB
MRCHMDB
Pseudomonic acidHMDB
BRL 4910aHMDB
Mupirocin, 14C-labeledHMDB
Mupirocin, calcium salt (2:1), dihydrateHMDB
14C-Labeled mupirocinHMDB
BRL-4910aHMDB
Mupirocin, 14C labeledHMDB
Mupirocin, lithium saltHMDB
Acid, pseudomonicHMDB
Mupirocin, calcium salt (2:1)HMDB
Mupirocin, sodium saltHMDB
Mupirocin calciumHMDB
Chemical FormulaC26H44O9
Average Molecular Mass500.622 g/mol
Monoisotopic Mass500.299 g/mol
CAS Registry Number12650-69-0
IUPAC Name9-{[(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 Namemupirocin
SMILESC[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 IdentifierInChI=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 KeyMINDHVHHQZYEEK-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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentMedium-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 FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.026 g/LALOGPS
logP2.25ALOGPS
logP2.45ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)4.83ChemAxon
pKa (Strongest Basic)-2.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area146.05 ŲChemAxon
Rotatable Bond Count17ChemAxon
Refractivity129.39 m³·mol⁻¹ChemAxon
Polarizability55.5 ųChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fc1-2972400000-21f057ea2a2e95898b9dSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00di-4966726000-06f4a51b9c0619130ac4Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-056r-1976100000-dfa28e3b7efa7b734a99Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0bwa-3920000000-b910c0ca6dcc91904891Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-056r-1976100000-dfa28e3b7efa7b734a99Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0bwa-3920000000-b910c0ca6dcc91904891Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-1342920000-677def34a6e414632f7eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0670-6981300000-69aa4a4ddd0866e13409Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0zgi-7920100000-472a053832ce780dd335Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0227900000-2b3bd45c30c76c00ada4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0kka-9776600000-a91ac251679e309216a5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0kml-9840000000-4c1976a6372a21fd11fdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-052k-0100900000-2ba1125d17b9a119cec1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-2132900000-b2848b38bb227b2c50baSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052n-4126900000-a6fe8de917ce81221d01Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fus-2126930000-8ef8418ebf22e9aa7d14Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-015d-9620200000-8cb94d45ef1676428b42Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-9600000000-177c92b81937ff998d8eSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB00410
HMDB IDHMDB0014554
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkMupirocin
Chemspider ID393914
ChEBI ID7025
PubChem Compound ID446596
Kegg Compound IDC11758
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=22500807
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=23337107
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=23535880
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=23543635
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=24625190
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=3101012
7. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
8. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10.
9. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20.
10. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.
11. The lipid handbook with CD-ROM