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Record Information
Creation Date2013-07-22 19:51:22 UTC
Update Date2016-02-11 08:19:23 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 organic compounds known as epoxy fatty acids. These are fatty acids containing an oxirane ring as part of the aliphatic chain.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentEpoxy fatty acids
Alternative Parents
  • Methyl-branched fatty acid
  • Epoxy fatty acid
  • Cyclohexanol
  • Branched fatty acid
  • Unsaturated fatty acid
  • Cyclic alcohol
  • Secondary alcohol
  • 1,2-diol
  • Oxacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Ether
  • Oxirane
  • Dialkyl ether
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • 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 QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
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. [2112164 ]