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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2013-07-22 19:51:19 UTC
Update Date2017-12-07 18:58:43 UTC
HMDB IDHMDB0061153
Secondary Accession Numbers
  • HMDB61153
Metabolite Identification
Common NameLorcaserin sulfamate
DescriptionLorcaserin sulfamate is a metabolite of lorcaserin. Lorcaserin (APD-356, trade name Lorqess) is a weight-loss drug developed by Arena Pharmaceuticals. It has serotonergic properties and acts as an anorectic. On 22 December 2009 a New Drug Application (NDA) was submitted to the Food and Drug Administration (FDA) in the United States. On 16 September 2010, an FDA advisory panel voted to recommend against approval of the drug based on concerns over both safety and efficacy. (Wikipedia)
Structure
Thumb
SynonymsNot Available
Chemical FormulaC11H14ClNO3S
Average Molecular Weight275.752
Monoisotopic Molecular Weight275.038291716
IUPAC Name8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine-3-sulfonic acid
Traditional Name8-chloro-1-methyl-1,2,4,5-tetrahydro-3-benzazepine-3-sulfonic acid
CAS Registry NumberNot Available
SMILES
CC1CN(CCC2=C1C=C(Cl)C=C2)S(O)(=O)=O
InChI Identifier
InChI=1S/C11H14ClNO3S/c1-8-7-13(17(14,15)16)5-4-9-2-3-10(12)6-11(8)9/h2-3,6,8H,4-5,7H2,1H3,(H,14,15,16)
InChI KeyYZUNJIOOIHWHGQ-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as benzazepines. These are organic compounds containing a benzene ring fused to an azepine ring (unsaturated seven-membered heterocycle with one nitrogen atom replacing a carbon atom).
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganoheterocyclic compounds
Sub ClassBenzazepines
Direct ParentBenzazepines
Alternative Parents
Substituents
  • Benzazepine
  • Azepine
  • Aryl chloride
  • Aryl halide
  • Sulfuric acid monoamide
  • Benzenoid
  • Organic sulfuric acid or derivatives
  • Azacycle
  • Organic nitrogen compound
  • Organochloride
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organohalogen compound
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic 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 Solubility0.046 g/LALOGPS
logP0.23ALOGPS
logP2.05ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)-1.3ChemAxon
pKa (Strongest Basic)-9.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area57.61 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity67.05 m³·mol⁻¹ChemAxon
Polarizability27.01 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, Positivesplash10-0fr6-0930000000-665399af058b1adef847View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0490000000-d45fc9db665cbd01e7d2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052g-0890000000-097132f44799f6a51b97View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uxr-1900000000-14dd1babde80ee8c96d1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-3090000000-97343f8dc3b6fce72d0bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00e9-5390000000-50d7b8f67af9d003f403View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-9200000000-4d9897202cc623fa4d67View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane (predicted from logP)
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 IDDBMET00900
      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