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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-06-15 17:14:09 UTC
Update Date2019-07-23 07:14:39 UTC
HMDB IDHMDB0060590
Secondary Accession Numbers
  • HMDB60590
Metabolite Identification
Common NameRoflumilast N-oxide
DescriptionRoflumilast N-oxide belongs to the class of organic compounds known as benzamides. These are organic compounds containing a carboxamido substituent attached to a benzene ring. Roflumilast N-oxide is an extremely weak basic (essentially neutral) compound (based on its pKa). Roflumilast N-oxide is a metabolite of roflumilast. 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). Roflumilast (trade names Daxas, Daliresp) is a drug which acts as a selective, long-acting inhibitor of the enzyme PDE-4.
Structure
Data?1563866079
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
Description Belongs to the class of organic compounds known as benzamides. These are organic compounds containing a carboxamido substituent attached to a benzene ring.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and 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
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 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+191.68130932474
DeepCCS[M-H]-189.32330932474
DeepCCS[M-2H]-222.38430932474
DeepCCS[M+Na]+197.77430932474
AllCCS[M+H]+187.032859911
AllCCS[M+H-H2O]+184.532859911
AllCCS[M+NH4]+189.332859911
AllCCS[M+Na]+190.032859911
AllCCS[M-H]-181.232859911
AllCCS[M+Na-2H]-180.632859911
AllCCS[M+HCOO]-180.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Roflumilast N-oxide[O-][N+]1=CC(Cl)=C(NC(=O)C2=CC(OCC3CC3)=C(OC(F)F)C=C2)C(Cl)=C14042.8Standard polar33892256
Roflumilast N-oxide[O-][N+]1=CC(Cl)=C(NC(=O)C2=CC(OCC3CC3)=C(OC(F)F)C=C2)C(Cl)=C12960.1Standard non polar33892256
Roflumilast N-oxide[O-][N+]1=CC(Cl)=C(NC(=O)C2=CC(OCC3CC3)=C(OC(F)F)C=C2)C(Cl)=C13351.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Roflumilast N-oxide,1TMS,isomer #1C[Si](C)(C)N(C(=O)C1=CC=C(OC(F)F)C(OCC2CC2)=C1)C1=C(Cl)C=[N+]([O-])C=C1Cl2809.8Semi standard non polar33892256
Roflumilast N-oxide,1TMS,isomer #1C[Si](C)(C)N(C(=O)C1=CC=C(OC(F)F)C(OCC2CC2)=C1)C1=C(Cl)C=[N+]([O-])C=C1Cl2750.9Standard non polar33892256
Roflumilast N-oxide,1TMS,isomer #1C[Si](C)(C)N(C(=O)C1=CC=C(OC(F)F)C(OCC2CC2)=C1)C1=C(Cl)C=[N+]([O-])C=C1Cl3369.3Standard polar33892256
Roflumilast N-oxide,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C(=O)C1=CC=C(OC(F)F)C(OCC2CC2)=C1)C1=C(Cl)C=[N+]([O-])C=C1Cl3082.7Semi standard non polar33892256
Roflumilast N-oxide,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C(=O)C1=CC=C(OC(F)F)C(OCC2CC2)=C1)C1=C(Cl)C=[N+]([O-])C=C1Cl2956.8Standard non polar33892256
Roflumilast N-oxide,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C(=O)C1=CC=C(OC(F)F)C(OCC2CC2)=C1)C1=C(Cl)C=[N+]([O-])C=C1Cl3429.9Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Roflumilast N-oxide GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f6x-9525100000-026a4326d0cbbb7299dc2017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Roflumilast N-oxide 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 - Roflumilast N-oxide 10V, Positive-QTOFsplash10-066r-4033900000-87938499d786f4c329c12017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Roflumilast N-oxide 20V, Positive-QTOFsplash10-0a4l-8395300000-616f098e64736a3e577c2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Roflumilast N-oxide 40V, Positive-QTOFsplash10-0a4i-9500000000-b3366d2b2654dc1e8c2a2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Roflumilast N-oxide 10V, Negative-QTOFsplash10-014i-0007900000-82c7a6a7e99aec6ee1d92017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Roflumilast N-oxide 20V, Negative-QTOFsplash10-03xr-2219300000-da706abf30181119f4a52017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Roflumilast N-oxide 40V, Negative-QTOFsplash10-004i-4934000000-afc412786cbcb3201d302017-10-06Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane (predicted from logP)
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 LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
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 ReferencesNot Available