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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2013-07-09 16:12:50 UTC
Update Date2019-07-23 07:15:35 UTC
HMDB IDHMDB0061018
Secondary Accession Numbers
  • HMDB61018
Metabolite Identification
Common Namenorcisapride
Descriptionnorcisapride belongs to the class of organic compounds known as diphenylpyrroles. These are aromatic heterocyclic compounds with a structure based on a pyrrole ring linked to exactly two phenyl groups. It acts directly as a serotonin 5-HT4 receptor agonist and indirectly as a parasympathomimetic. norcisapride is a very strong basic compound (based on its pKa). norcisapride is a metabolite of cisapride. Cisapride acts through the stimulation of the serotonin 5-HT4 receptors which increases acetylcholine release in the enteric nervous system (specifically the myenteric plexus). Ticalopride is an isomer of the active metabolite of cisapride. It has been sold under the trade names Prepulsid (Janssen-Ortho) and Propulsid (in the U.S.). This results in increased tone and amplitude of gastric (especially antral) contractions, relaxation of the pyloric sphincter and the duodenal bulb, and increased peristalsis of the duodenum and jejunum resulting in accelerated gastric emptying and intestinal transit. Cisapride is a gastroprokinetic agent, a drug which increases motility in the upper gastrointestinal tract. Stimulation of the serotonin receptors increases acetylcholine release in the enteric nervous system. It was discovered by Janssen Pharmaceutica in 1980.
Structure
Data?1563866135
SynonymsNot Available
Chemical FormulaC14H20ClN3O3
Average Molecular Weight313.78
Monoisotopic Molecular Weight313.119319228
IUPAC Name4-amino-5-chloro-2-methoxy-N-[(3S,4R)-3-methoxypiperidin-4-yl]benzene-1-carboximidic acid
Traditional Name4-amino-5-chloro-2-methoxy-N-[(3S,4R)-3-methoxypiperidin-4-yl]benzenecarboximidic acid
CAS Registry NumberNot Available
SMILES
CO[C@H]1CNCC[C@H]1N=C(O)C1=C(OC)C=C(N)C(Cl)=C1
InChI Identifier
InChI=1S/C14H20ClN3O3/c1-20-12-6-10(16)9(15)5-8(12)14(19)18-11-3-4-17-7-13(11)21-2/h5-6,11,13,17H,3-4,7,16H2,1-2H3,(H,18,19)/t11-,13+/m1/s1
InChI KeyOMLDMGPCWMBPAN-YPMHNXCESA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as diphenylpyrroles. These are aromatic heterocyclic compounds with a structure based on a pyrrole ring linked to exactly two phenyl groups.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyrroles
Sub ClassSubstituted pyrroles
Direct ParentDiphenylpyrroles
Alternative Parents
Substituents
  • 2,3-diphenylpyrrole
  • Aromatic anilide
  • Medium-chain hydroxy acid
  • Pyrrole-3-carboxamide
  • Pyrrole-3-carboxylic acid or derivatives
  • Medium-chain fatty acid
  • Beta-hydroxy acid
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Fluorobenzene
  • Halobenzene
  • Halogenated fatty acid
  • Heterocyclic fatty acid
  • Hydroxy fatty acid
  • Phenol
  • Aryl fluoride
  • Aryl halide
  • Monocyclic benzene moiety
  • Hydroxy acid
  • Fatty acyl
  • Fatty acid
  • Benzenoid
  • Vinylogous amide
  • Heteroaromatic compound
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Carboxamide group
  • Monocarboxylic acid or derivatives
  • Azacycle
  • Carboxylic acid derivative
  • Carboxylic acid
  • Organofluoride
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Organooxygen compound
  • Organic nitrogen compound
  • Alcohol
  • Carbonyl group
  • Organohalogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source:

Biological location:

Role

Industrial application:

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 Solubility0.34 g/LALOGPS
logP0.86ALOGPS
logP-0.63ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)7.77ChemAxon
pKa (Strongest Basic)9.53ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area89.1 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity82.53 m³·mol⁻¹ChemAxon
Polarizability32.45 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03dr-7950000000-74b28b56bf109763b643Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0229-9466000000-b032224f3fe378c427f4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0379000000-ea7895363ec2230274eeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-2971000000-32ede446940570afd05fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0frt-5930000000-d47454a494c1c9aefbc0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0259000000-4177c98f339d036c6c66Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-097j-4592000000-46d112a57b8bcc43fc56Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4m-4920000000-c68c719657d7a5169cbaSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
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 IDDB06422
      Phenol Explorer Compound 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 Compound216236
      PDB IDNot Available
      ChEBI IDNot Available
      Food Biomarker OntologyNot Available
      VMH IDNot Available
      References
      Synthesis ReferenceNot Available
      Material Safety Data Sheet (MSDS)Not Available
      General ReferencesNot Available