You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version3.6
Creation Date2013-07-09 16:06:22 UTC
Update Date2017-08-15 23:27:19 UTC
HMDB IDHMDB0060904
Secondary Accession Numbers
  • HMDB60904
Metabolite Identification
Common NameHaloperidol glucuronide
DescriptionHaloperidol glucuronide 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 FormulaC27H31ClFNO8
Average Molecular Weight551.988
Monoisotopic Molecular Weight551.172222885
IUPAC Name(2S,3S,4S,5R)-6-{[4-(4-chlorophenyl)-1-[4-(4-fluorophenyl)-4-oxobutyl]piperidin-4-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
Traditional Name(2S,3S,4S,5R)-6-{[4-(4-chlorophenyl)-1-[4-(4-fluorophenyl)-4-oxobutyl]piperidin-4-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
CAS Registry NumberNot Available
SMILES
O[C@@H]1[C@@H](O)C(OC2(CCN(CCCC(=O)C3=CC=C(F)C=C3)CC2)C2=CC=C(Cl)C=C2)O[C@@H]([C@H]1O)C(O)=O
InChI Identifier
InChI=1S/C27H31ClFNO8/c28-18-7-5-17(6-8-18)27(38-26-23(34)21(32)22(33)24(37-26)25(35)36)11-14-30(15-12-27)13-1-2-20(31)16-3-9-19(29)10-4-16/h3-10,21-24,26,32-34H,1-2,11-15H2,(H,35,36)/t21-,22-,23+,24-,26?/m0/s1
InChI KeyZFNLYKVTHNLKNZ-BFZHNPFYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as o-glucuronides. These are glucuronides in which the aglycone is linked to the carbohydrate unit through an O-glycosidic bond.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic oxygen compounds
Sub ClassOrganooxygen compounds
Direct ParentO-glucuronides
Alternative Parents
Substituents
  • O-glucuronide
  • 1-o-glucuronide
  • Alkyl-phenylketone
  • Hexose monosaccharide
  • Phenylpiperidine
  • O-glycosyl compound
  • Phenylbutylamine
  • Butyrophenone
  • Glycosyl compound
  • Phenylketone
  • Benzoyl
  • Aryl alkyl ketone
  • Aryl ketone
  • Beta-hydroxy acid
  • Aralkylamine
  • Halobenzene
  • Chlorobenzene
  • Fluorobenzene
  • Aryl halide
  • Piperidine
  • Aryl fluoride
  • Aryl chloride
  • Oxane
  • Monocyclic benzene moiety
  • Pyran
  • Monosaccharide
  • Gamma-aminoketone
  • Hydroxy acid
  • Benzenoid
  • Amino acid or derivatives
  • Amino acid
  • Tertiary aliphatic amine
  • Tertiary amine
  • Secondary alcohol
  • Ketone
  • Monocarboxylic acid or derivatives
  • Oxacycle
  • Azacycle
  • Carboxylic acid derivative
  • Carboxylic acid
  • Organoheterocyclic compound
  • Acetal
  • Polyol
  • Organohalogen compound
  • Organochloride
  • Hydrocarbon derivative
  • Alcohol
  • Carbonyl group
  • Organic nitrogen compound
  • Organofluoride
  • Organonitrogen compound
  • Amine
  • Organopnictogen compound
  • Organic oxide
  • 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
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 Solubility0.13 mg/mLALOGPS
logP2.55ALOGPS
logP-0.52ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)3.17ChemAxon
pKa (Strongest Basic)8.24ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area136.76 Å2ChemAxon
Rotatable Bond Count9ChemAxon
Refractivity134.87 m3·mol-1ChemAxon
Polarizability55.82 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
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 IDDBMET00105
      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 LinkHMDB0060904
      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