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Record Information
Version3.6
Creation Date2013-07-22 19:51:41 UTC
Update Date2016-02-11 08:19:27 UTC
HMDB IDHMDB61159
Secondary Accession NumbersNone
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=1/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?/s2
InChI KeyInChIKey=DGFKLWZCLRDMAF-ZDNHGVAONA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds 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).
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzazepines
Sub ClassNot Available
Direct ParentBenzazepines
Alternative Parents
Substituents
  • Benzazepine
  • Pyran carboxylic acid
  • Pyran carboxylic acid or derivatives
  • Azepine
  • Benzenoid
  • Pyran
  • Oxane
  • Dicarboxylic acid or derivatives
  • Saccharide
  • Aryl halide
  • Aryl chloride
  • Tertiary amine
  • Oxacycle
  • Azacycle
  • Carboxylic acid
  • Carboxylic acid derivative
  • Acetal
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Carbonyl group
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic 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 Solubility0.016 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity105.14 m3·mol-1ChemAxon
Polarizability43.37 Å3ChemAxon
Number of Rings3ChemAxon
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 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
NuGOwiki LinkHMDB61159
Metagene LinkHMDB61159
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