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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-07-22 19:51:22 UTC
Update Date2021-09-14 15:39:07 UTC
HMDB IDHMDB0061154
Secondary Accession Numbers
  • HMDB61154
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 )
Structure
Data?1563866152
Synonyms
ValueSource
MonateGenerator
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
SMILES
[H][C@]1(O[C@H]1CC1CC[C@@H](C\C(C)=C\C(O)=O)[C@H](O)[C@@H]1O)[C@@H](C)C(C)O
InChI Identifier
InChI=1S/C18H30O6/c1-9(7-15(20)21)6-12-4-5-13(17(23)16(12)22)8-14-18(24-14)10(2)11(3)19/h7,10-14,16-19,22-23H,4-6,8H2,1-3H3,(H,20,21)/b9-7+/t10-,11?,12-,13?,14-,16-,17+,18-/m0/s1
InChI KeyMUWNEQMGMLXEFO-CXSJRMNRSA-N
Chemical Taxonomy
Description 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
Substituents
  • 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
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.06 g/LALOGPS
logP0.52ALOGPS
logP1.06ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)4.64ChemAxon
pKa (Strongest Basic)-2.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area110.52 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity89.07 m³·mol⁻¹ChemAxon
Polarizability37.35 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+181.44631661259
DarkChem[M-H]-178.19931661259
DeepCCS[M+H]+188.73930932474
DeepCCS[M-H]-186.34430932474
DeepCCS[M-2H]-219.41830932474
DeepCCS[M+Na]+195.39430932474
AllCCS[M+H]+187.432859911
AllCCS[M+H-H2O]+184.632859911
AllCCS[M+NH4]+190.032859911
AllCCS[M+Na]+190.832859911
AllCCS[M-H]-187.332859911
AllCCS[M+Na-2H]-188.332859911
AllCCS[M+HCOO]-189.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Monic acid[H][C@]1(O[C@H]1CC1CC[C@@H](C\C(C)=C\C(O)=O)[C@H](O)[C@@H]1O)[C@@H](C)C(C)O4315.9Standard polar33892256
Monic acid[H][C@]1(O[C@H]1CC1CC[C@@H](C\C(C)=C\C(O)=O)[C@H](O)[C@@H]1O)[C@@H](C)C(C)O2605.4Standard non polar33892256
Monic acid[H][C@]1(O[C@H]1CC1CC[C@@H](C\C(C)=C\C(O)=O)[C@H](O)[C@@H]1O)[C@@H](C)C(C)O2754.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Monic acid,1TMS,isomer #1C/C(=C\C(=O)O[Si](C)(C)C)C[C@@H]1CCC(C[C@@H]2O[C@H]2[C@@H](C)C(C)O)[C@@H](O)[C@H]1O2671.5Semi standard non polar33892256
Monic acid,1TMS,isomer #2C/C(=C\C(=O)O)C[C@@H]1CCC(C[C@@H]2O[C@H]2[C@@H](C)C(C)O)[C@@H](O)[C@H]1O[Si](C)(C)C2639.8Semi standard non polar33892256
Monic acid,1TMS,isomer #3C/C(=C\C(=O)O)C[C@@H]1CCC(C[C@@H]2O[C@H]2[C@@H](C)C(C)O)[C@@H](O[Si](C)(C)C)[C@H]1O2638.6Semi standard non polar33892256
Monic acid,1TMS,isomer #4C/C(=C\C(=O)O)C[C@@H]1CCC(C[C@@H]2O[C@H]2[C@@H](C)C(C)O[Si](C)(C)C)[C@@H](O)[C@H]1O2688.4Semi standard non polar33892256
Monic acid,2TMS,isomer #1C/C(=C\C(=O)O[Si](C)(C)C)C[C@@H]1CCC(C[C@@H]2O[C@H]2[C@@H](C)C(C)O[Si](C)(C)C)[C@@H](O)[C@H]1O2663.7Semi standard non polar33892256
Monic acid,2TMS,isomer #2C/C(=C\C(=O)O[Si](C)(C)C)C[C@@H]1CCC(C[C@@H]2O[C@H]2[C@@H](C)C(C)O)[C@@H](O[Si](C)(C)C)[C@H]1O2620.9Semi standard non polar33892256
Monic acid,2TMS,isomer #3C/C(=C\C(=O)O[Si](C)(C)C)C[C@@H]1CCC(C[C@@H]2O[C@H]2[C@@H](C)C(C)O)[C@@H](O)[C@H]1O[Si](C)(C)C2606.5Semi standard non polar33892256
Monic acid,2TMS,isomer #4C/C(=C\C(=O)O)C[C@@H]1CCC(C[C@@H]2O[C@H]2[C@@H](C)C(C)O[Si](C)(C)C)[C@@H](O)[C@H]1O[Si](C)(C)C2670.2Semi standard non polar33892256
Monic acid,2TMS,isomer #5C/C(=C\C(=O)O)C[C@@H]1CCC(C[C@@H]2O[C@H]2[C@@H](C)C(C)O)[C@@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C2651.5Semi standard non polar33892256
Monic acid,2TMS,isomer #6C/C(=C\C(=O)O)C[C@@H]1CCC(C[C@@H]2O[C@H]2[C@@H](C)C(C)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H]1O2685.4Semi standard non polar33892256
Monic acid,3TMS,isomer #1C/C(=C\C(=O)O[Si](C)(C)C)C[C@@H]1CCC(C[C@@H]2O[C@H]2[C@@H](C)C(C)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H]1O2639.7Semi standard non polar33892256
Monic acid,3TMS,isomer #2C/C(=C\C(=O)O[Si](C)(C)C)C[C@@H]1CCC(C[C@@H]2O[C@H]2[C@@H](C)C(C)O[Si](C)(C)C)[C@@H](O)[C@H]1O[Si](C)(C)C2611.8Semi standard non polar33892256
Monic acid,3TMS,isomer #3C/C(=C\C(=O)O[Si](C)(C)C)C[C@@H]1CCC(C[C@@H]2O[C@H]2[C@@H](C)C(C)O)[C@@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C2596.7Semi standard non polar33892256
Monic acid,3TMS,isomer #4C/C(=C\C(=O)O)C[C@@H]1CCC(C[C@@H]2O[C@H]2[C@@H](C)C(C)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C2659.9Semi standard non polar33892256
Monic acid,4TMS,isomer #1C/C(=C\C(=O)O[Si](C)(C)C)C[C@@H]1CCC(C[C@@H]2O[C@H]2[C@@H](C)C(C)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C2619.3Semi standard non polar33892256
Monic acid,1TBDMS,isomer #1C/C(=C\C(=O)O[Si](C)(C)C(C)(C)C)C[C@@H]1CCC(C[C@@H]2O[C@H]2[C@@H](C)C(C)O)[C@@H](O)[C@H]1O2896.1Semi standard non polar33892256
Monic acid,1TBDMS,isomer #2C/C(=C\C(=O)O)C[C@@H]1CCC(C[C@@H]2O[C@H]2[C@@H](C)C(C)O)[C@@H](O)[C@H]1O[Si](C)(C)C(C)(C)C2887.9Semi standard non polar33892256
Monic acid,1TBDMS,isomer #3C/C(=C\C(=O)O)C[C@@H]1CCC(C[C@@H]2O[C@H]2[C@@H](C)C(C)O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]1O2876.3Semi standard non polar33892256
Monic acid,1TBDMS,isomer #4C/C(=C\C(=O)O)C[C@@H]1CCC(C[C@@H]2O[C@H]2[C@@H](C)C(C)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H]1O2955.2Semi standard non polar33892256
Monic acid,2TBDMS,isomer #1C/C(=C\C(=O)O[Si](C)(C)C(C)(C)C)C[C@@H]1CCC(C[C@@H]2O[C@H]2[C@@H](C)C(C)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H]1O3149.1Semi standard non polar33892256
Monic acid,2TBDMS,isomer #2C/C(=C\C(=O)O[Si](C)(C)C(C)(C)C)C[C@@H]1CCC(C[C@@H]2O[C@H]2[C@@H](C)C(C)O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]1O3075.6Semi standard non polar33892256
Monic acid,2TBDMS,isomer #3C/C(=C\C(=O)O[Si](C)(C)C(C)(C)C)C[C@@H]1CCC(C[C@@H]2O[C@H]2[C@@H](C)C(C)O)[C@@H](O)[C@H]1O[Si](C)(C)C(C)(C)C3063.6Semi standard non polar33892256
Monic acid,2TBDMS,isomer #4C/C(=C\C(=O)O)C[C@@H]1CCC(C[C@@H]2O[C@H]2[C@@H](C)C(C)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H]1O[Si](C)(C)C(C)(C)C3138.4Semi standard non polar33892256
Monic acid,2TBDMS,isomer #5C/C(=C\C(=O)O)C[C@@H]1CCC(C[C@@H]2O[C@H]2[C@@H](C)C(C)O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]1O[Si](C)(C)C(C)(C)C3087.2Semi standard non polar33892256
Monic acid,2TBDMS,isomer #6C/C(=C\C(=O)O)C[C@@H]1CCC(C[C@@H]2O[C@H]2[C@@H](C)C(C)O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]1O3134.6Semi standard non polar33892256
Monic acid,3TBDMS,isomer #1C/C(=C\C(=O)O[Si](C)(C)C(C)(C)C)C[C@@H]1CCC(C[C@@H]2O[C@H]2[C@@H](C)C(C)O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]1O3313.5Semi standard non polar33892256
Monic acid,3TBDMS,isomer #2C/C(=C\C(=O)O[Si](C)(C)C(C)(C)C)C[C@@H]1CCC(C[C@@H]2O[C@H]2[C@@H](C)C(C)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H]1O[Si](C)(C)C(C)(C)C3309.5Semi standard non polar33892256
Monic acid,3TBDMS,isomer #3C/C(=C\C(=O)O[Si](C)(C)C(C)(C)C)C[C@@H]1CCC(C[C@@H]2O[C@H]2[C@@H](C)C(C)O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]1O[Si](C)(C)C(C)(C)C3263.6Semi standard non polar33892256
Monic acid,3TBDMS,isomer #4C/C(=C\C(=O)O)C[C@@H]1CCC(C[C@@H]2O[C@H]2[C@@H](C)C(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)C3340.0Semi standard non polar33892256
Monic acid,4TBDMS,isomer #1C/C(=C\C(=O)O[Si](C)(C)C(C)(C)C)C[C@@H]1CCC(C[C@@H]2O[C@H]2[C@@H](C)C(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)C3499.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Monic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0095-9467000000-2afd4130843c2ad8e89d2017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Monic acid GC-MS (4 TMS) - 70eV, Positivesplash10-014i-1800449000-d401b70ceced92a825fd2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Monic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Monic acid 10V, Positive-QTOFsplash10-056r-1049000000-a7226eb85976b545db062017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Monic acid 20V, Positive-QTOFsplash10-07gi-6393000000-302582cb8b9200ef10652017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Monic acid 40V, Positive-QTOFsplash10-0gc9-9420000000-c62e53171bac899c3e3a2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Monic acid 10V, Negative-QTOFsplash10-006x-0198000000-a4fc56197eef205118f82017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Monic acid 20V, Negative-QTOFsplash10-00fr-6093000000-7f949004e886a4facc5f2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Monic acid 40V, Negative-QTOFsplash10-05fr-9020000000-22d33ac086c5bf86df302017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Monic acid 10V, Negative-QTOFsplash10-002f-0079000000-113116320d521335dad32021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Monic acid 20V, Negative-QTOFsplash10-056u-0093000000-0943e4dce172d49d585b2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Monic acid 40V, Negative-QTOFsplash10-0a4r-1193000000-b5245ab73d3d7b48be272021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Monic acid 10V, Positive-QTOFsplash10-004l-0397000000-cf697b3c5b7124b66b482021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Monic acid 20V, Positive-QTOFsplash10-0a4i-2495000000-8c5069063d568c3317d62021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Monic acid 40V, Positive-QTOFsplash10-000x-9000000000-cc67e9d53157aa0d51072021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkTravedona-Monate
METLIN IDNot Available
PubChem Compound131770055
PDB IDNot Available
ChEBI IDNot Available
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. Pappa KA: The clinical development of mupirocin. J Am Acad Dermatol. 1990 May;22(5 Pt 1):873-9. [PubMed:2112164 ]
  2. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.