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Record Information
Version4.0
Creation Date2013-06-15 18:06:14 UTC
Update Date2017-10-23 19:15:45 UTC
HMDB IDHMDB0060621
Secondary Accession Numbers
  • HMDB60621
Metabolite Identification
Common Namen-Demethylated piperazine
Descriptionn-Demethylated piperazine is a metabolite of imatinib. Imatinib (originally STI571) is a drug used to treat certain cancers. It is marketed by Novartis as Gleevec or Glivec as its mesylate salt, imatinib mesilate. Imatinib is the first of a new class of drugs that act by specifically inhibiting a certain enzyme – a receptor tyrosine kinase – that is characteristic of a particular cancer cell, rather than non-specifically inhibiting and killing all rapidly dividing cells. (Wikipedia)
Structure
Thumb
Synonyms
ValueSource
CGP74588HMDB
Chemical FormulaC28H29N7O
Average Molecular Weight479.5762
Monoisotopic Molecular Weight479.243358585
IUPAC NameN-(4-methyl-3-{[4-(pyridin-3-yl)pyrimidin-2-yl]amino}phenyl)-4-(piperazin-1-ylmethyl)benzamide
Traditional NameN-(4-methyl-3-{[4-(pyridin-3-yl)pyrimidin-2-yl]amino}phenyl)-4-(piperazin-1-ylmethyl)benzamide
CAS Registry NumberNot Available
SMILES
CC1=C(NC2=NC=CC(=N2)C2=CN=CC=C2)C=C(NC(=O)C2=CC=C(CN3CCNCC3)C=C2)C=C1
InChI Identifier
InChI=1S/C28H29N7O/c1-20-4-9-24(17-26(20)34-28-31-12-10-25(33-28)23-3-2-11-30-18-23)32-27(36)22-7-5-21(6-8-22)19-35-15-13-29-14-16-35/h2-12,17-18,29H,13-16,19H2,1H3,(H,32,36)(H,31,33,34)
InChI KeyBQQYXPHRXIZMDM-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as benzanilides. These are aromatic compounds containing an anilide group in which the carboxamide group is substituted with a benzene ring. They have the general structure RNC(=O)R', where R,R'= benzene.
KingdomChemical entities
Super ClassOrganic compounds
ClassBenzenoids
Sub ClassBenzene and substituted derivatives
Direct ParentBenzanilides
Alternative Parents
Substituents
  • Benzanilide
  • Pyridinylpyrimidine
  • Benzamide
  • Benzoic acid or derivatives
  • Diaminotoluene
  • Benzoyl
  • Benzylamine
  • Phenylmethylamine
  • Aniline or substituted anilines
  • Aminopyrimidine
  • Aralkylamine
  • Toluene
  • N-alkylpiperazine
  • 1,4-diazinane
  • Piperazine
  • Pyridine
  • Pyrimidine
  • Heteroaromatic compound
  • Tertiary aliphatic amine
  • Tertiary amine
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Amino acid or derivatives
  • Secondary amine
  • Organoheterocyclic compound
  • Azacycle
  • Carboxylic acid derivative
  • Secondary aliphatic amine
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Amine
  • 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 Solubility0.0066 g/LALOGPS
logP3.16ALOGPS
logP3.99ChemAxon
logS-4.9ALOGPS
pKa (Strongest Acidic)12.46ChemAxon
pKa (Strongest Basic)9.25ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area95.07 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity143.63 m³·mol⁻¹ChemAxon
Polarizability53.39 ųChemAxon
Number of Rings5ChemAxon
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, Positivesplash10-0f9f-9364300000-17e27cc3c2e4a0cb7501View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0144900000-dbf028ef8689f34d3771View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f6x-1698400000-6206b8b45fb71b15fcdfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00mo-4921000000-dd971eb0dcec023353d9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-1110900000-89aea60502d7f5f0c44aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-7535900000-6f9446f0c31d2b676c94View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9400000000-e4bc361c68b0c77b4951View 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 IDDBMET00931
      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