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Record Information
Creation Date2013-07-22 19:51:22 UTC
Update Date2017-03-02 22:05:47 UTC
Secondary Accession NumbersNone
Metabolite Identification
Common NameMonic acid
DescriptionMonic acid is a metabolite of mupirocin. Mupirocin (Bactroban or Centany) is an antibiotic originally isolated from Pseudomonas fluorescens NCIMB 10586, developed by Beecham. Mupirocin is bacteriostatic at low concentrations and bactericidal at high concentrations. It is used topically and is effective against Gram-positive bacteria, including MRSA. Mupirocin is a mixture of several pseudomonic acids, with pseudomonic acid A (PA-A) constituting greater than 90% of the mixture. (Wikipedia) No systemic absorption of mupirocin or its major metabolite, monic acid, has been detected in short courses of topical administration to healthy volunteers or to patients with epidermolysis bullosa after prolonged courses of therapy with Bactroban ointment. (PMID: 2112164 )
SynonymsNot Available
Chemical FormulaC18H30O6
Average Molecular Weight342.4272
Monoisotopic Molecular Weight342.204238692
IUPAC Name(2E)-4-[(1S,2S,3R)-2,3-dihydroxy-4-{[(2S,3S)-3-[(2S)-3-hydroxybutan-2-yl]oxiran-2-yl]methyl}cyclohexyl]-3-methylbut-2-enoic acid
Traditional Name(2E)-4-[(1S,2S,3R)-2,3-dihydroxy-4-{[(2S,3S)-3-[(2S)-3-hydroxybutan-2-yl]oxiran-2-yl]methyl}cyclohexyl]-3-methylbut-2-enoic acid
CAS Registry NumberNot Available
InChI Identifier
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as epoxy fatty acids. These are fatty acids containing an oxirane ring as part of the aliphatic chain.
KingdomChemical entities
Super ClassOrganic compounds
ClassLipids and lipid-like molecules
Sub ClassFatty Acyls
Direct ParentEpoxy fatty acids
Alternative Parents
  • Branched fatty acid
  • Cyclohexanol
  • Epoxy fatty acid
  • Hydroxy fatty acid
  • Short-chain hydroxy acid
  • Methyl-branched fatty acid
  • Unsaturated fatty acid
  • Cyclic alcohol
  • Secondary alcohol
  • Oxacycle
  • Organoheterocyclic compound
  • Carboxylic acid
  • Carboxylic acid derivative
  • Dialkyl ether
  • Oxirane
  • Ether
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Hydrocarbon derivative
  • Alcohol
  • Organic oxygen compound
  • Carbonyl group
  • Organooxygen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
StatusExpected but not Quantified
  • Drug metabolite
  • Waste products
ApplicationNot Available
Cellular locations
  • Cytoplasm
Physical Properties
StateNot Available
Experimental Properties
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
Water Solubility1.06 mg/mLALOGPS
pKa (Strongest Acidic)4.64ChemAxon
pKa (Strongest Basic)-2.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area110.52 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity89.07 m3·mol-1ChemAxon
Polarizability37.35 Å3ChemAxon
Number of Rings2ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
Normal Concentrations
BloodExpected but not Quantified Not AvailableNot AvailableNormal
    UrineExpected but not Quantified Not AvailableNot AvailableNormal
      Abnormal Concentrations
      Not Available
      Associated Disorders and Diseases
      Disease ReferencesNone
      Associated OMIM IDsNone
      DrugBank IDNot Available
      DrugBank Metabolite IDDBMET00912
      Phenol Explorer Compound IDNot Available
      Phenol Explorer Metabolite IDNot Available
      FoodDB IDNot Available
      KNApSAcK IDNot Available
      Chemspider IDNot Available
      KEGG Compound IDNot Available
      BioCyc IDNot Available
      BiGG IDNot Available
      Wikipedia LinkNot Available
      NuGOwiki LinkHMDB61154
      Metagene LinkHMDB61154
      METLIN IDNot Available
      PubChem CompoundNot Available
      PDB IDNot Available
      ChEBI IDNot Available
      Synthesis ReferenceNot Available
      Material Safety Data Sheet (MSDS)Not Available
      General References
      1. Pappa KA: The clinical development of mupirocin. J Am Acad Dermatol. 1990 May;22(5 Pt 1):873-9. [PubMed:2112164 ]