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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2013-06-15 17:14:09 UTC
Update Date2017-10-23 19:15:44 UTC
HMDB IDHMDB0060590
Secondary Accession Numbers
  • HMDB60590
Metabolite Identification
Common NameRoflumilast N-oxide
DescriptionRoflumilast N-oxide is a metabolite of roflumilast. Roflumilast (trade names Daxas, Daliresp) is a drug which acts as a selective, long-acting inhibitor of the enzyme PDE-4. It has antiinflammatory effects and is under development as an orally administered drug for the treatment of inflammatory conditions of the lungs such as asthma, and chronic obstructive pulmonary disease (COPD). (Wikipedia)
Structure
Thumb
SynonymsNot Available
Chemical FormulaC17H14Cl2F2N2O4
Average Molecular Weight419.207
Monoisotopic Molecular Weight418.02986877
IUPAC Name3,5-dichloro-4-[3-(cyclopropylmethoxy)-4-(difluoromethoxy)benzamido]pyridin-1-ium-1-olate
Traditional Name3,5-dichloro-4-[3-(cyclopropylmethoxy)-4-(difluoromethoxy)benzamido]pyridin-1-ium-1-olate
CAS Registry NumberNot Available
SMILES
[O-][N+]1=CC(Cl)=C(NC(=O)C2=CC(OCC3CC3)=C(OC(F)F)C=C2)C(Cl)=C1
InChI Identifier
InChI=1S/C17H14Cl2F2N2O4/c18-11-6-23(25)7-12(19)15(11)22-16(24)10-3-4-13(27-17(20)21)14(5-10)26-8-9-1-2-9/h3-7,9,17H,1-2,8H2,(H,22,24)
InChI KeyPCGSQNPMMSALEJ-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as benzamides. These are organic compounds containing a carboxamido substituent attached to a benzene ring.
KingdomChemical entities
Super ClassOrganic compounds
ClassBenzenoids
Sub ClassBenzene and substituted derivatives
Direct ParentBenzamides
Alternative Parents
Substituents
  • Benzamide
  • Phenoxy compound
  • Benzoyl
  • Polyhalopyridine
  • Phenol ether
  • Alkyl aryl ether
  • Aryl chloride
  • Aryl halide
  • Pyridinium
  • Pyridine
  • Heteroaromatic compound
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Azacycle
  • Carboxylic acid derivative
  • Ether
  • Organoheterocyclic compound
  • Organochloride
  • Organohalogen compound
  • Alkyl halide
  • Alkyl fluoride
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organofluoride
  • Organonitrogen compound
  • Organooxygen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Organ and components:

Source:

Role

Biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0022 g/LALOGPS
logP4.17ALOGPS
logP3.19ChemAxon
logS-5.3ALOGPS
pKa (Strongest Acidic)7.26ChemAxon
pKa (Strongest Basic)-0.32ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area73.02 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity97.61 m³·mol⁻¹ChemAxon
Polarizability36.17 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f6x-9525100000-026a4326d0cbbb7299dcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-066r-4033900000-87938499d786f4c329c1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4l-8395300000-616f098e64736a3e577cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9500000000-b3366d2b2654dc1e8c2aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0007900000-82c7a6a7e99aec6ee1d9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03xr-2219300000-da706abf30181119f4a5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-4934000000-afc412786cbcb3201d30View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableNormal
    details
    UrineExpected but not Quantified Not AvailableNot AvailableNormal
      details
      Abnormal Concentrations
      Not Available
      Associated Disorders and Diseases
      Disease ReferencesNone
      Associated OMIM IDsNone
      DrugBank IDNot Available
      DrugBank Metabolite IDDBMET00997
      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
      METLIN IDNot Available
      PubChem CompoundNot Available
      PDB IDNot Available
      ChEBI IDNot Available
      References
      Synthesis ReferenceNot Available
      Material Safety Data Sheet (MSDS)Not Available
      General ReferencesNot Available