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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-07-09 16:11:49 UTC
Update Date2019-07-23 07:15:33 UTC
HMDB IDHMDB0061000
Secondary Accession Numbers
  • HMDB61000
Metabolite Identification
Common Name4-(4-Chlorophenyl)-1-[4-(4-fluorophenyl)-4-oxobutyl]-pyridinium (HPP+)
Description4-(4-Chlorophenyl)-1-[4-(4-fluorophenyl)-4-oxobutyl]-pyridinium (HPP+), also known as N-(4'-fluorobutyrophenone)-4-(4-chlorophenyl)pyridinium perchlorate or 4-CFOBP, belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group. It is in the butyrophenone class of antipsychotic medications and has pharmacological effects similar to the phenothiazines. 4-(4-Chlorophenyl)-1-[4-(4-fluorophenyl)-4-oxobutyl]-pyridinium (HPP+) is a very strong basic compound (based on its pKa). Haloperidol is a typical antipsychotic. Haloperidol is an older antipsychotic used in the treatment of schizophrenia and acute psychotic states and delirium. 4-(4-Chlorophenyl)-1--pyridinium (HPP+) is a metabolite of haloperidol.
Structure
Data?1563866133
Synonyms
ValueSource
BCPP(+)HMDB
4-CFOBPHMDB
4-(4-Chlorophenyl)-1-(4-(4-fluorophenyl)-4-oxobutyl)pyridiniumHMDB
HPP(+)HMDB
N-(4'-Fluorobutyrophenone)-4-(4-chlorophenyl)pyridinium perchlorateHMDB
N-(4'-Fluorobutyrophenone)-4-(4-chlorophenyl)pyridiniumHMDB
N-(4'-Fluorobutyrophenone)-4-(4-chlorophenyl)pyridinium chlorideHMDB
N-(4'-Fluorobutyrophenone)-4-(4-chlorophenyl)pyridinium iodideHMDB
Chemical FormulaC21H18ClFNO
Average Molecular Weight354.825
Monoisotopic Molecular Weight354.106095115
IUPAC Name(4-{1-[4-(4-fluorophenyl)-4-oxobutyl]-1,4-dihydropyridin-4-ylidene}cyclohexa-2,5-dien-1-ylidene)-lambda3-chloranylium
Traditional Name(4-{1-[4-(4-fluorophenyl)-4-oxobutyl]pyridin-4-ylidene}cyclohexa-2,5-dien-1-ylidene)-lambda3-chloranylium
CAS Registry NumberNot Available
SMILES
[H]C1=C([H])C(=C([H])C([H])=C1F)C(=O)C([H])([H])C([H])([H])C([H])([H])[N+]1=C([H])C([H])=C(C([H])=C1[H])C1=C([H])C([H])=C(Cl)C([H])=C1[H]
InChI Identifier
InChI=1S/C21H18ClFNO/c22-19-7-3-16(4-8-19)17-11-14-24(15-12-17)13-1-2-21(25)18-5-9-20(23)10-6-18/h3-12,14-15H,1-2,13H2/q+1
InChI KeyKAPIKUHBALFONG-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentAlkyl-phenylketones
Alternative Parents
Substituents
  • Alkyl-phenylketone
  • 4-phenylpyridine
  • Butyrophenone
  • Phenylbutylamine
  • Benzoyl
  • Aryl alkyl ketone
  • Chlorobenzene
  • Fluorobenzene
  • Halobenzene
  • Benzenoid
  • Pyridinium
  • Pyridine
  • Aryl halide
  • Monocyclic benzene moiety
  • Aryl chloride
  • Aryl fluoride
  • Heteroaromatic compound
  • Azacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organohalogen compound
  • Organochloride
  • Organopnictogen compound
  • Organic nitrogen compound
  • Organofluoride
  • Organonitrogen compound
  • Organic cation
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic 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 Solubility0.0095 g/LALOGPS
logP0.81ALOGPS
logP3.9ChemAxon
logS-7.3ALOGPS
pKa (Strongest Acidic)16.28ChemAxon
pKa (Strongest Basic)5.93ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area20.31 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity105.69 m³·mol⁻¹ChemAxon
Polarizability38.07 ųChemAxon
Number of Rings3ChemAxon
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+H]+180.53930932474
DeepCCS[M-H]-178.70730932474
DeepCCS[M-2H]-212.73930932474
DeepCCS[M+Na]+186.54330932474
AllCCS[M+H]+179.432859911
AllCCS[M+H-H2O]+176.832859911
AllCCS[M+NH4]+181.932859911
AllCCS[M+Na]+182.632859911
AllCCS[M-H]-184.332859911
AllCCS[M+Na-2H]-184.132859911
AllCCS[M+HCOO]-184.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
4-(4-Chlorophenyl)-1-[4-(4-fluorophenyl)-4-oxobutyl]-pyridinium (HPP+)[H]C1=C([H])C(=C([H])C([H])=C1F)C(=O)C([H])([H])C([H])([H])C([H])([H])[N+]1=C([H])C([H])=C(C([H])=C1[H])C1=C([H])C([H])=C(Cl)C([H])=C1[H]4109.6Standard polar33892256
4-(4-Chlorophenyl)-1-[4-(4-fluorophenyl)-4-oxobutyl]-pyridinium (HPP+)[H]C1=C([H])C(=C([H])C([H])=C1F)C(=O)C([H])([H])C([H])([H])C([H])([H])[N+]1=C([H])C([H])=C(C([H])=C1[H])C1=C([H])C([H])=C(Cl)C([H])=C1[H]2864.7Standard non polar33892256
4-(4-Chlorophenyl)-1-[4-(4-fluorophenyl)-4-oxobutyl]-pyridinium (HPP+)[H]C1=C([H])C(=C([H])C([H])=C1F)C(=O)C([H])([H])C([H])([H])C([H])([H])[N+]1=C([H])C([H])=C(C([H])=C1[H])C1=C([H])C([H])=C(Cl)C([H])=C1[H]2960.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 4-(4-Chlorophenyl)-1-[4-(4-fluorophenyl)-4-oxobutyl]-pyridinium (HPP+) GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-2932000000-144791f11f1ca9cf7bd42017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-(4-Chlorophenyl)-1-[4-(4-fluorophenyl)-4-oxobutyl]-pyridinium (HPP+) 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 - 4-(4-Chlorophenyl)-1-[4-(4-fluorophenyl)-4-oxobutyl]-pyridinium (HPP+) 10V, Positive-QTOFsplash10-0udi-1129000000-3967db8d1574362a56d62017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-(4-Chlorophenyl)-1-[4-(4-fluorophenyl)-4-oxobutyl]-pyridinium (HPP+) 20V, Positive-QTOFsplash10-0uem-2595000000-3347289c9640ea489c1c2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-(4-Chlorophenyl)-1-[4-(4-fluorophenyl)-4-oxobutyl]-pyridinium (HPP+) 40V, Positive-QTOFsplash10-00dj-6910000000-05c96f5fb306729ff6162017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-(4-Chlorophenyl)-1-[4-(4-fluorophenyl)-4-oxobutyl]-pyridinium (HPP+) 10V, Positive-QTOFsplash10-0udi-0209000000-80bee477b1ab1172ee082021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-(4-Chlorophenyl)-1-[4-(4-fluorophenyl)-4-oxobutyl]-pyridinium (HPP+) 20V, Positive-QTOFsplash10-0uxr-0915000000-87ef5dcde95f33671a5a2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-(4-Chlorophenyl)-1-[4-(4-fluorophenyl)-4-oxobutyl]-pyridinium (HPP+) 40V, Positive-QTOFsplash10-01ox-0910000000-d716f8fa2be0be5caf1e2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane (predicted from logP)
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 Compound9975463
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