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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-07-04 18:53:47 UTC
Update Date2021-09-14 15:25:43 UTC
HMDB IDHMDB0060704
Secondary Accession Numbers
  • HMDB60704
Metabolite Identification
Common Name1-Hydroxylorcaserin
Description1-Hydroxylorcaserin 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
Data?1563866093
SynonymsNot Available
Chemical FormulaC11H14ClNO
Average Molecular Weight211.688
Monoisotopic Molecular Weight211.076391782
IUPAC Name8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepin-1-ol
Traditional Name8-chloro-1-methyl-2,3,4,5-tetrahydro-3-benzazepin-1-ol
CAS Registry NumberNot Available
SMILES
CC1(O)CNCCC2=CC=C(Cl)C=C12
InChI Identifier
InChI=1S/C11H14ClNO/c1-11(14)7-13-5-4-8-2-3-9(12)6-10(8)11/h2-3,6,13-14H,4-5,7H2,1H3
InChI KeyAHFHLPCZDZHXDN-UHFFFAOYSA-N
Chemical Taxonomy
Description 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
  • Azepine
  • Aralkylamine
  • Aryl chloride
  • Aryl halide
  • Benzenoid
  • Tertiary alcohol
  • 1,2-aminoalcohol
  • Secondary amine
  • Secondary aliphatic amine
  • Azacycle
  • Amine
  • Organooxygen compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Alcohol
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.86 g/LALOGPS
logP1.83ALOGPS
logP1.83ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)13.88ChemAxon
pKa (Strongest Basic)9.46ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area32.26 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity58.02 m³·mol⁻¹ChemAxon
Polarizability22.18 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M-2H]-179.24830932474
DeepCCS[M+Na]+154.85930932474
AllCCS[M+H]+144.132859911
AllCCS[M+H-H2O]+139.932859911
AllCCS[M+NH4]+148.032859911
AllCCS[M+Na]+149.232859911
AllCCS[M-H]-146.532859911
AllCCS[M+Na-2H]-147.032859911
AllCCS[M+HCOO]-147.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
1-HydroxylorcaserinCC1(O)CNCCC2=CC=C(Cl)C=C122707.6Standard polar33892256
1-HydroxylorcaserinCC1(O)CNCCC2=CC=C(Cl)C=C121722.1Standard non polar33892256
1-HydroxylorcaserinCC1(O)CNCCC2=CC=C(Cl)C=C121736.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
1-Hydroxylorcaserin,1TMS,isomer #1CC1(O[Si](C)(C)C)CNCCC2=CC=C(Cl)C=C211814.8Semi standard non polar33892256
1-Hydroxylorcaserin,1TMS,isomer #2CC1(O)CN([Si](C)(C)C)CCC2=CC=C(Cl)C=C211893.7Semi standard non polar33892256
1-Hydroxylorcaserin,2TMS,isomer #1CC1(O[Si](C)(C)C)CN([Si](C)(C)C)CCC2=CC=C(Cl)C=C211919.0Semi standard non polar33892256
1-Hydroxylorcaserin,2TMS,isomer #1CC1(O[Si](C)(C)C)CN([Si](C)(C)C)CCC2=CC=C(Cl)C=C211921.2Standard non polar33892256
1-Hydroxylorcaserin,2TMS,isomer #1CC1(O[Si](C)(C)C)CN([Si](C)(C)C)CCC2=CC=C(Cl)C=C212180.9Standard polar33892256
1-Hydroxylorcaserin,1TBDMS,isomer #1CC1(O[Si](C)(C)C(C)(C)C)CNCCC2=CC=C(Cl)C=C212061.7Semi standard non polar33892256
1-Hydroxylorcaserin,1TBDMS,isomer #2CC1(O)CN([Si](C)(C)C(C)(C)C)CCC2=CC=C(Cl)C=C212102.7Semi standard non polar33892256
1-Hydroxylorcaserin,2TBDMS,isomer #1CC1(O[Si](C)(C)C(C)(C)C)CN([Si](C)(C)C(C)(C)C)CCC2=CC=C(Cl)C=C212381.5Semi standard non polar33892256
1-Hydroxylorcaserin,2TBDMS,isomer #1CC1(O[Si](C)(C)C(C)(C)C)CN([Si](C)(C)C(C)(C)C)CCC2=CC=C(Cl)C=C212404.2Standard non polar33892256
1-Hydroxylorcaserin,2TBDMS,isomer #1CC1(O[Si](C)(C)C(C)(C)C)CN([Si](C)(C)C(C)(C)C)CCC2=CC=C(Cl)C=C212437.5Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 1-Hydroxylorcaserin GC-MS (Non-derivatized) - 70eV, Positivesplash10-00mn-0900000000-91bc8b4290fa86812a562017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 1-Hydroxylorcaserin GC-MS (1 TMS) - 70eV, Positivesplash10-00xr-9380000000-da0c38548279a24103d52017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 1-Hydroxylorcaserin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Hydroxylorcaserin 10V, Positive-QTOFsplash10-01ox-0960000000-4bb45c7a5fc13c528b2f2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Hydroxylorcaserin 20V, Positive-QTOFsplash10-0006-0910000000-acce6601b04a390410532017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Hydroxylorcaserin 40V, Positive-QTOFsplash10-0a70-2900000000-135dcb14dc64114709062017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Hydroxylorcaserin 10V, Negative-QTOFsplash10-03di-0290000000-a1ac45eace910bc814572017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Hydroxylorcaserin 20V, Negative-QTOFsplash10-03dl-0890000000-946944b83b4b44cd9c842017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Hydroxylorcaserin 40V, Negative-QTOFsplash10-0596-7900000000-a11476ed167dd25892612017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Hydroxylorcaserin 10V, Positive-QTOFsplash10-03di-0490000000-d73b437a6ae2043f72362021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Hydroxylorcaserin 20V, Positive-QTOFsplash10-0006-0900000000-7c0ef6398e157cda0f332021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Hydroxylorcaserin 40V, Positive-QTOFsplash10-0pb9-0900000000-95ab26bba5540500e3952021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Hydroxylorcaserin 10V, Negative-QTOFsplash10-03di-0190000000-7118172057564f684c122021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Hydroxylorcaserin 20V, Negative-QTOFsplash10-01q9-9270000000-c22b5e3964eac3089df92021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Hydroxylorcaserin 40V, Negative-QTOFsplash10-001i-9200000000-025ab79ef545fab464992021-10-12Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB 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 Compound77570492
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available