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Record Information
Version4.0
Creation Date2013-07-09 16:19:03 UTC
Update Date2017-09-23 15:16:57 UTC
HMDB IDHMDB0061109
Secondary Accession Numbers
  • HMDB61109
Metabolite Identification
Common Name5-Hydroxybuspirone
Description5-Hydroxybuspirone is a metabolite of buspirone. Buspirone is an anxiolytic psychoactive drug of the azapirone chemical class, and is primarily used to treat generalized anxiety disorder (GAD) Bristol-Myers Squibb (BMS) gained FDA approval of buspirone in 1986 for treatment of GAD. The patent on Buspar by Bristol-Myers Squibb expired in 2001, and buspirone is available as a generic. (Wikipedia)
Structure
Thumb
SynonymsNot Available
Chemical FormulaC21H31N5O3
Average Molecular Weight401.5025
Monoisotopic Molecular Weight401.242689883
IUPAC Name8-{4-[4-(5-hydroxypyrimidin-2-yl)piperazin-1-yl]butyl}-8-azaspiro[4.5]decane-7,9-dione
Traditional Name8-{4-[4-(5-hydroxypyrimidin-2-yl)piperazin-1-yl]butyl}-8-azaspiro[4.5]decane-7,9-dione
CAS Registry NumberNot Available
SMILES
OC1=CN=C(N=C1)N1CCN(CCCCN2C(=O)CC3(CCCC3)CC2=O)CC1
InChI Identifier
InChI=1S/C21H31N5O3/c27-17-15-22-20(23-16-17)25-11-9-24(10-12-25)7-3-4-8-26-18(28)13-21(14-19(26)29)5-1-2-6-21/h15-16,27H,1-14H2
InChI KeyWKAUDMPUKWYRBF-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as n-arylpiperazines. These are organic compounds containing a piperazine ring where the nitrogen ring atom carries an aryl group.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganoheterocyclic compounds
Sub ClassDiazinanes
Direct ParentN-arylpiperazines
Alternative Parents
Substituents
  • Azaspirodecanedione
  • N-arylpiperazine
  • Azaspirodecane
  • Piperidinedione
  • Dialkylarylamine
  • Aminopyrimidine
  • Delta-lactam
  • Hydroxypyrimidine
  • N-alkylpiperazine
  • Piperidinone
  • Carboxylic acid imide, n-substituted
  • Piperidine
  • Pyrimidine
  • Carboxylic acid imide
  • Dicarboximide
  • Heteroaromatic compound
  • Lactam
  • Amino acid or derivatives
  • Tertiary aliphatic amine
  • Tertiary amine
  • Carboxylic acid derivative
  • Azacycle
  • Organic nitrogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Amine
  • Carbonyl group
  • Organopnictogen compound
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Drug metabolite
  • Endogenous
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 Solubility1.08 mg/mLALOGPS
logP2.25ALOGPS
logP1.29ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)9.43ChemAxon
pKa (Strongest Basic)7.55ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area89.87 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity110.87 m3·mol-1ChemAxon
Polarizability45.19 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
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 IDDBMET00479
      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 LinkHMDB0061109
      METLIN IDNot Available
      PubChem Compound59964599
      PDB IDNot Available
      ChEBI IDNot Available
      References
      Synthesis ReferenceNot Available
      Material Safety Data Sheet (MSDS)Not Available
      General ReferencesNot Available