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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2022-03-07 02:51:39 UTC
HMDB IDHMDB0014554
Secondary Accession Numbers
  • HMDB14554
Metabolite Identification
Common NameMupirocin
DescriptionMupirocin (pseudomonic acid A, or Bactroban or Centany) is an antibiotic originally isolated from Pseudomonas fluorescens. It is used topically, and is primarily effective against Gram-positive bacteria. Mupirocin is bacteriostatic at low concentrations and bactericidal at high concentrations. Mupirocin has a unique mechanism of action, which is selective binding to bacterial isoleucyl-tRNA synthetase, which halts the incorporation of isoleucine into bacterial proteins. Because this mechanism of action is not shared with any other antibiotic, mupirocin has few problems of antibiotic cross-resistance.
Structure
Data?1582753192
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 Weight500.6222
Monoisotopic Molecular Weight500.298533006
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
CAS Registry Number12650-69-0
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 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
Ontology
Disposition

Biological location

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point77 - 78 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.026 g/LNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+223.94631661259
DarkChem[M-H]-216.23631661259
DeepCCS[M+H]+210.90330932474
DeepCCS[M-H]-208.57830932474
DeepCCS[M-2H]-241.55930932474
DeepCCS[M+Na]+216.64430932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
MupirocinC[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]1O5518.8Standard polar33892256
MupirocinC[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]1O3457.3Standard non polar33892256
MupirocinC[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]1O3669.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Mupirocin,1TMS,isomer #1C/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[Si](C)(C)C)[C@@H](O)[C@H]1O3596.3Semi standard non polar33892256
Mupirocin,1TMS,isomer #2C/C(=C\C(=O)OCCCCCCCCC(=O)O[Si](C)(C)C)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]1O3580.8Semi standard non polar33892256
Mupirocin,1TMS,isomer #3C/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[Si](C)(C)C3591.5Semi standard non polar33892256
Mupirocin,1TMS,isomer #4C/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[Si](C)(C)C)[C@H]1O3569.5Semi standard non polar33892256
Mupirocin,2TMS,isomer #1C/C(=C\C(=O)OCCCCCCCCC(=O)O[Si](C)(C)C)C[C@@H]1OC[C@H](C[C@@H]2O[C@H]2[C@@H](C)[C@H](C)O[Si](C)(C)C)[C@@H](O)[C@H]1O3551.6Semi standard non polar33892256
Mupirocin,2TMS,isomer #2C/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[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H]1O3551.2Semi standard non polar33892256
Mupirocin,2TMS,isomer #3C/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[Si](C)(C)C)[C@@H](O)[C@H]1O[Si](C)(C)C3587.4Semi standard non polar33892256
Mupirocin,2TMS,isomer #4C/C(=C\C(=O)OCCCCCCCCC(=O)O[Si](C)(C)C)C[C@@H]1OC[C@H](C[C@@H]2O[C@H]2[C@@H](C)[C@H](C)O)[C@@H](O[Si](C)(C)C)[C@H]1O3524.5Semi standard non polar33892256
Mupirocin,2TMS,isomer #5C/C(=C\C(=O)OCCCCCCCCC(=O)O[Si](C)(C)C)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[Si](C)(C)C3571.2Semi standard non polar33892256
Mupirocin,2TMS,isomer #6C/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[Si](C)(C)C)[C@H]1O[Si](C)(C)C3540.9Semi standard non polar33892256
Mupirocin,3TMS,isomer #1C/C(=C\C(=O)OCCCCCCCCC(=O)O[Si](C)(C)C)C[C@@H]1OC[C@H](C[C@@H]2O[C@H]2[C@@H](C)[C@H](C)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H]1O3507.5Semi standard non polar33892256
Mupirocin,3TMS,isomer #2C/C(=C\C(=O)OCCCCCCCCC(=O)O[Si](C)(C)C)C[C@@H]1OC[C@H](C[C@@H]2O[C@H]2[C@@H](C)[C@H](C)O[Si](C)(C)C)[C@@H](O)[C@H]1O[Si](C)(C)C3561.1Semi standard non polar33892256
Mupirocin,3TMS,isomer #3C/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[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C3536.5Semi standard non polar33892256
Mupirocin,3TMS,isomer #4C/C(=C\C(=O)OCCCCCCCCC(=O)O[Si](C)(C)C)C[C@@H]1OC[C@H](C[C@@H]2O[C@H]2[C@@H](C)[C@H](C)O)[C@@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C3501.6Semi standard non polar33892256
Mupirocin,4TMS,isomer #1C/C(=C\C(=O)OCCCCCCCCC(=O)O[Si](C)(C)C)C[C@@H]1OC[C@H](C[C@@H]2O[C@H]2[C@@H](C)[C@H](C)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C3483.3Semi standard non polar33892256
Mupirocin,1TBDMS,isomer #1C/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[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H]1O3835.0Semi standard non polar33892256
Mupirocin,1TBDMS,isomer #2C/C(=C\C(=O)OCCCCCCCCC(=O)O[Si](C)(C)C(C)(C)C)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]1O3843.9Semi standard non polar33892256
Mupirocin,1TBDMS,isomer #3C/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[Si](C)(C)C(C)(C)C3820.1Semi standard non polar33892256
Mupirocin,1TBDMS,isomer #4C/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[Si](C)(C)C(C)(C)C)[C@H]1O3784.7Semi standard non polar33892256
Mupirocin,2TBDMS,isomer #1C/C(=C\C(=O)OCCCCCCCCC(=O)O[Si](C)(C)C(C)(C)C)C[C@@H]1OC[C@H](C[C@@H]2O[C@H]2[C@@H](C)[C@H](C)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H]1O4049.2Semi standard non polar33892256
Mupirocin,2TBDMS,isomer #2C/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[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]1O4007.8Semi standard non polar33892256
Mupirocin,2TBDMS,isomer #3C/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[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H]1O[Si](C)(C)C(C)(C)C4029.4Semi standard non polar33892256
Mupirocin,2TBDMS,isomer #4C/C(=C\C(=O)OCCCCCCCCC(=O)O[Si](C)(C)C(C)(C)C)C[C@@H]1OC[C@H](C[C@@H]2O[C@H]2[C@@H](C)[C@H](C)O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]1O3986.1Semi standard non polar33892256
Mupirocin,2TBDMS,isomer #5C/C(=C\C(=O)OCCCCCCCCC(=O)O[Si](C)(C)C(C)(C)C)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[Si](C)(C)C(C)(C)C4014.6Semi standard non polar33892256
Mupirocin,2TBDMS,isomer #6C/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[Si](C)(C)C(C)(C)C)[C@H]1O[Si](C)(C)C(C)(C)C3994.9Semi standard non polar33892256
Mupirocin,3TBDMS,isomer #1C/C(=C\C(=O)OCCCCCCCCC(=O)O[Si](C)(C)C(C)(C)C)C[C@@H]1OC[C@H](C[C@@H]2O[C@H]2[C@@H](C)[C@H](C)O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]1O4182.2Semi standard non polar33892256
Mupirocin,3TBDMS,isomer #2C/C(=C\C(=O)OCCCCCCCCC(=O)O[Si](C)(C)C(C)(C)C)C[C@@H]1OC[C@H](C[C@@H]2O[C@H]2[C@@H](C)[C@H](C)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H]1O[Si](C)(C)C(C)(C)C4217.7Semi standard non polar33892256
Mupirocin,3TBDMS,isomer #3C/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[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]1O[Si](C)(C)C(C)(C)C4215.6Semi standard non polar33892256
Mupirocin,3TBDMS,isomer #4C/C(=C\C(=O)OCCCCCCCCC(=O)O[Si](C)(C)C(C)(C)C)C[C@@H]1OC[C@H](C[C@@H]2O[C@H]2[C@@H](C)[C@H](C)O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]1O[Si](C)(C)C(C)(C)C4179.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Mupirocin GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fc1-2972400000-21f057ea2a2e95898b9d2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Mupirocin GC-MS (2 TMS) - 70eV, Positivesplash10-00di-4966726000-06f4a51b9c0619130ac42017-10-06Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Mupirocin LC-ESI-qTof , Positive-QTOFsplash10-056r-1976100000-dfa28e3b7efa7b734a992017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Mupirocin LC-ESI-qTof , Positive-QTOFsplash10-0bwa-3920000000-b910c0ca6dcc919048912017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Mupirocin , positive-QTOFsplash10-056r-1976100000-dfa28e3b7efa7b734a992017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Mupirocin , positive-QTOFsplash10-0bwa-3920000000-b910c0ca6dcc919048912017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mupirocin 10V, Positive-QTOFsplash10-001i-1342920000-677def34a6e414632f7e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mupirocin 20V, Positive-QTOFsplash10-0670-6981300000-69aa4a4ddd0866e134092016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mupirocin 40V, Positive-QTOFsplash10-0zgi-7920100000-472a053832ce780dd3352016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mupirocin 10V, Negative-QTOFsplash10-0002-0227900000-2b3bd45c30c76c00ada42016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mupirocin 20V, Negative-QTOFsplash10-0kka-9776600000-a91ac251679e309216a52016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mupirocin 40V, Negative-QTOFsplash10-0kml-9840000000-4c1976a6372a21fd11fd2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mupirocin 10V, Negative-QTOFsplash10-052k-0100900000-2ba1125d17b9a119cec12021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mupirocin 20V, Negative-QTOFsplash10-000i-2132900000-b2848b38bb227b2c50ba2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mupirocin 40V, Negative-QTOFsplash10-052n-4126900000-a6fe8de917ce81221d012021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mupirocin 10V, Positive-QTOFsplash10-0fus-2126930000-8ef8418ebf22e9aa7d142021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mupirocin 20V, Positive-QTOFsplash10-015d-9620200000-8cb94d45ef1676428b422021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mupirocin 40V, Positive-QTOFsplash10-0a4l-9600000000-177c92b81937ff998d8e2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00410 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00410 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00410
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID393914
KEGG Compound IDC11758
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMupirocin
METLIN IDNot Available
PubChem Compound446596
PDB IDNot Available
ChEBI ID7025
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. 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. [PubMed:16902246 ]
  3. 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. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.