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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2013-07-22 19:51:41 UTC
Update Date2017-12-07 18:59:35 UTC
HMDB IDHMDB0061159
Secondary Accession Numbers
  • HMDB61159
Metabolite Identification
Common NameN-Carbamoyl glucuronide lorcaserin
DescriptionN-Carbamoyl glucuronide lorcaserin 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 FormulaC21H28ClNO5
Average Molecular Weight409.904
Monoisotopic Molecular Weight409.165600718
IUPAC Name(2R,3R,4R,5S)-6-(8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine-3-carbonyloxy)-3,4,5-trimethyloxane-2-carboxylic acid
Traditional Name(2R,3R,4R,5S)-6-(8-chloro-1-methyl-1,2,4,5-tetrahydro-3-benzazepine-3-carbonyloxy)-3,4,5-trimethyloxane-2-carboxylic acid
CAS Registry NumberNot Available
SMILES
C[C@H]1[C@H](C)C(OC(=O)N2CCC3=C(C=C(Cl)C=C3)C(C)C2)O[C@H]([C@@H]1C)C(O)=O
InChI Identifier
InChI=1S/C21H28ClNO5/c1-11-10-23(8-7-15-5-6-16(22)9-17(11)15)21(26)28-20-14(4)12(2)13(3)18(27-20)19(24)25/h5-6,9,11-14,18,20H,7-8,10H2,1-4H3,(H,24,25)/t11?,12-,13-,14+,18-,20?/m1/s1
InChI KeyDGFKLWZCLRDMAF-IJQUCLSUSA-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
  • Benzenoid
  • Pyran
  • Oxane
  • Carbamic acid ester
  • Carbonic acid derivative
  • Acetal
  • Oxacycle
  • Azacycle
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic nitrogen compound
  • Organohalogen compound
  • Organochloride
  • Organonitrogen compound
  • Organooxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • 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 Solubility0.016 g/LALOGPS
logP3.83ALOGPS
logP4.78ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)3.8ChemAxon
pKa (Strongest Basic)-4.4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area76.07 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity105.14 m³·mol⁻¹ChemAxon
Polarizability43.37 ųChemAxon
Number of Rings3ChemAxon
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, Positivesplash10-0a4l-9302000000-02f966742e4a14f60076View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-01b9-9332200000-91ad6657e8e1f7d7afcfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01vo-0793400000-137b2dc683df9fa71bdaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-1961000000-589fe39adefa411787a3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0zfs-4900000000-fa5ace59409de12a7778View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-05fr-0191400000-ad997e7ed7366a9f2dbbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00dl-0893100000-47de7825905e2b4584a8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0076-5960000000-984698109eb9fc1969afView 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 IDDBMET00927
      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