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Record Information
Version3.6
Creation Date2013-07-09 16:11:49 UTC
Update Date2016-02-11 08:16:50 UTC
HMDB IDHMDB61000
Secondary Accession NumbersNone
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+) is a metabolite of haloperidol. Haloperidol is a typical antipsychotic. It is in the butyrophenone class of antipsychotic medications and has pharmacological effects similar to the phenothiazines. Haloperidol is an older antipsychotic used in the treatment of schizophrenia and acute psychotic states and delirium. (Wikipedia)
Structure
Thumb
SynonymsNot Available
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)-λ³-chloranylium
Traditional Name(4-{1-[4-(4-fluorophenyl)-4-oxobutyl]pyridin-4-ylidene}cyclohexa-2,5-dien-1-ylidene)-λ³-chloranylium
CAS Registry NumberNot Available
SMILES
FC1=CC=C(C=C1)C(=O)CCCN1C=CC(C=C1)=C1C=CC(=[Cl+])C=C1
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 KeyInChIKey=KAPIKUHBALFONG-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as phenylbutylamines. These are compounds containing a phenylbutylamine moiety, which consists of a phenyl group substituted at the fourth carbon by an butan-1-amine.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenylbutylamines
Direct ParentPhenylbutylamines
Alternative Parents
Substituents
  • Phenylbutylamine
  • Butyrophenone
  • Acetophenone
  • Aryl alkyl ketone
  • Aryl ketone
  • Benzoyl
  • Halobenzene
  • Fluorobenzene
  • Dihydropyridine
  • Hydropyridine
  • Gamma-aminoketone
  • Aryl halide
  • Aryl fluoride
  • Tertiary amine
  • Ketone
  • Azacycle
  • Organoheterocyclic compound
  • Enamine
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organofluoride
  • Organohalogen compound
  • Carbonyl group
  • Amine
  • Organic cation
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic 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 Solubility0.0095 mg/mLALOGPS
logP3.87ALOGPS
logP3.9ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)16.28ChemAxon
pKa (Strongest Basic)5.93ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area20.31 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity105.69 m3·mol-1ChemAxon
Polarizability38.07 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 IDDBMET00333
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 LinkHMDB61000
Metagene LinkHMDB61000
METLIN IDNot Available
PubChem Compound9975463
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available