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Record Information
Version3.6
Creation Date2013-06-15 18:06:14 UTC
Update Date2016-02-11 08:09:30 UTC
HMDB IDHMDB60621
Secondary Accession NumbersNone
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=CC=C(NC(=O)C2=CC=C(CN3CCNCC3)C=C2)C=C1NC1=NC=CC(=N1)C1=CN=CC=C1
InChI Identifier
InChI=1/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 KeyInChIKey=BQQYXPHRXIZMDM-UHFFFAOYNA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as n-phenylbenzamides. These are benzamides that are N-linked to a phenyl group via the carboxamide group.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzamides
Direct ParentN-phenylbenzamides
Alternative Parents
Substituents
  • N-phenylbenzamide
  • Pyridinylpyrimidine
  • N-arylamide
  • Diaminotoluene
  • Benzoic acid or derivatives
  • Aminotoluene
  • Phenylmethylamine
  • Benzylamine
  • Benzoyl
  • Aralkylamine
  • N-alkylpiperazine
  • Toluene
  • Pyrimidine
  • Pyridine
  • Piperazine
  • 1,4-diazinane
  • Heteroaromatic compound
  • Tertiary aliphatic amine
  • Tertiary amine
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Azacycle
  • Organoheterocyclic compound
  • Secondary amine
  • Secondary aliphatic amine
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Drug metabolite
Biofunction
  • Waste products
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Membrane (predicted from logP)
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 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity143.63 m3·mol-1ChemAxon
Polarizability53.39 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
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
NuGOwiki LinkHMDB60621
Metagene LinkHMDB60621
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