mupirocin (PAMDB100066)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB100066
Identification
Name: mupirocin
Description:An α,β-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
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • Pseudomonic acid A
Chemical Formula: C26H44O9
Average Molecular Weight: 500.6222
Monoisotopic Molecular Weight: 500.299
InChI Key: MINDHVHHQZYEEK-HBBNESRFSA-N
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
CAS number: Not Available
IUPAC Name:9-({(2E)-4-[(2
Traditional IUPAC Name: Not Available
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
Chemical Taxonomy
Taxonomy DescriptionThis compound 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 ClassLipids and lipid-like molecules
Class Fatty Acyls
Sub ClassFatty 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, secondary alcohol, epoxide, triol, alpha,beta-unsaturated carboxylic ester, oxanes (CHEBI:7025)
Physical Properties
State: Not Available
Charge:0
Melting point: Not Available
Experimental Properties: Not Available
Predicted Properties
PropertyValueSource
Mass500.6211ChemAxon
logP2.5925ChemAxon
H-bond acceptors9ChemAxon
H-bond donors4ChemAxon
Rotatable bonds17ChemAxon
PSA146.0500ChemAxon
RO5 violations1ChemAxon
RO3 violations5ChemAxon
Refractivity131.1062ChemAxon
Atoms79ChemAxon
Rings2ChemAxon
Heavy atoms35ChemAxon
Hydrogen atoms44ChemAxon
Heteroatoms9ChemAxon
N/O atoms9ChemAxon
Inorganic atoms0ChemAxon
Halogen atoms0ChemAxon
Chiral centers8ChemAxon
R/S chiral centers8ChemAxon
Unknown chiral centers0ChemAxon
Undefined chiral centers0ChemAxon
Stereo double bonds1ChemAxon
Cis/trans stereo double bonds0ChemAxon
Unknown stereo double bonds1ChemAxon
Undefined stereo double bonds 0ChemAxon
Biological Properties
Cellular Locations: Not Available
Reactions:
Pathways:
    Spectra
    Spectra: Not Available
    References
    References:
    • Melo JA, Ruvkun G. Inactivation of conserved C. elegans genes engages pathogen- and xenobiotic-associated defenses. Cell. 2012 Apr 13;149(2):452-66. Pubmed: 22500807
    Synthesis Reference: Not Available
    Material Safety Data Sheet (MSDS) Not Available
    External Links:
    ResourceLink
    KEGG DRUGD01076