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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2013-07-04 19:02:22 UTC
Update Date2017-12-07 18:10:58 UTC
HMDB IDHMDB0060831
Secondary Accession Numbers
  • HMDB60831
Metabolite Identification
Common Namemeta-O-Dealkylated flecainide
Descriptionmeta-O-Dealkylated flecainide is a metabolite of flecainide. Flecainide acetate is a class Ic antiarrhythmic agent used to prevent and treat tachyarrhythmias (abnormal fast rhythms of the heart). It is used to treat a variety of cardiac arrhythmias including paroxysmal atrial fibrillation (episodic irregular heartbeat originating in the upper chamber of the heart), paroxysmal supraventricular tachycardia (episodic rapid but regular heartbeat originating in the atrium), and ventricular tachycardia (rapid rhythms of the lower chambers of the heart). (Wikipedia)
Structure
Thumb
Synonyms
ValueSource
5-Hydroxy-N-(2-piperidinylmethyl)-2-(2,2,2-trifluoroethoxy)benzamideMeSH
MODFMeSH
Chemical FormulaC15H19F3N2O3
Average Molecular Weight332.3182
Monoisotopic Molecular Weight332.134777099
IUPAC Name5-hydroxy-N-(piperidin-2-ylmethyl)-2-(2,2,2-trifluoroethoxy)benzamide
Traditional Name5-hydroxy-N-(piperidin-2-ylmethyl)-2-(2,2,2-trifluoroethoxy)benzamide
CAS Registry NumberNot Available
SMILES
OC1=CC=C(OCC(F)(F)F)C(=C1)C(=O)NCC1CCCCN1
InChI Identifier
InChI=1S/C15H19F3N2O3/c16-15(17,18)9-23-13-5-4-11(21)7-12(13)14(22)20-8-10-3-1-2-6-19-10/h4-5,7,10,19,21H,1-3,6,8-9H2,(H,20,22)
InChI KeyFVJPPEWHZCSTAC-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
  • 4-alkoxyphenol
  • Benzamide
  • Phenoxy compound
  • Benzoyl
  • Phenol ether
  • Alkyl aryl ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Piperidine
  • Amino acid or derivatives
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Carboxylic acid derivative
  • Secondary aliphatic amine
  • Ether
  • Azacycle
  • Organoheterocyclic compound
  • Secondary amine
  • Organohalogen compound
  • Alkyl halide
  • Alkyl fluoride
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organofluoride
  • Organonitrogen compound
  • Organooxygen compound
  • Amine
  • Organic oxygen 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 Solubility0.092 g/LALOGPS
logP2.29ALOGPS
logP1.26ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)9.12ChemAxon
pKa (Strongest Basic)9.78ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area70.59 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity78.46 m³·mol⁻¹ChemAxon
Polarizability31.34 ųChemAxon
Number of Rings2ChemAxon
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, Positivesplash10-00sj-9272000000-82f100221b0a392c9032View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00ej-9125000000-8396432eef72e6e7b8c6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-4229000000-daa21495bf6c565e5c7dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000t-9332000000-0b112630dd47c34d2f1aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-9000000000-5720c7eb1f5a890af12cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0019000000-3b132af0c25abae1d5f3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-3569000000-63563a7909396b71cb6cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000x-9840000000-766b0c57f2cba44c8c28View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
NameSMPDB/PathwhizKEGG
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 IDDBMET00905
      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