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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2013-07-09 16:18:59 UTC
Update Date2017-12-07 18:51:11 UTC
HMDB IDHMDB0061108
Secondary Accession Numbers
  • HMDB61108
Metabolite Identification
Common Name3'-Hydroxybuspirone
Description3'-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 Name2-hydroxy-8-{4-[4-(pyrimidin-2-yl)piperazin-1-yl]butyl}-8-azaspiro[4.5]decane-7,9-dione
Traditional Name2-hydroxy-8-{4-[4-(pyrimidin-2-yl)piperazin-1-yl]butyl}-8-azaspiro[4.5]decane-7,9-dione
CAS Registry NumberNot Available
SMILES
OC1CCC2(C1)CC(=O)N(CCCCN1CCN(CC1)C1=NC=CC=N1)C(=O)C2
InChI Identifier
InChI=1S/C21H31N5O3/c27-17-4-5-21(14-17)15-18(28)26(19(29)16-21)9-2-1-8-24-10-12-25(13-11-24)20-22-6-3-7-23-20/h3,6-7,17,27H,1-2,4-5,8-16H2
InChI KeyRQGHABOPJRYOEZ-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as n-arylpiperazines. These are organic compounds containing a piperazine ring where the nitrogen ring atom carries an aryl group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDiazinanes
Sub ClassPiperazines
Direct ParentN-arylpiperazines
Alternative Parents
Substituents
  • Azaspirodecanedione
  • N-arylpiperazine
  • Azaspirodecane
  • Piperidinedione
  • Dialkylarylamine
  • Aminopyrimidine
  • N-alkylpiperazine
  • Delta-lactam
  • Piperidinone
  • Carboxylic acid imide, n-substituted
  • Pyrimidine
  • Piperidine
  • Heteroaromatic compound
  • Carboxylic acid imide
  • Cyclic alcohol
  • Dicarboximide
  • Amino acid or derivatives
  • Tertiary aliphatic amine
  • Tertiary amine
  • Lactam
  • Secondary alcohol
  • Carboxylic acid derivative
  • Azacycle
  • Organic oxide
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Amine
  • Carbonyl group
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
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 Solubility2.28 g/LALOGPS
logP1.2ALOGPS
logP0.39ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)18.38ChemAxon
pKa (Strongest Basic)7.62ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area89.87 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity110.56 m³·mol⁻¹ChemAxon
Polarizability45.15 ųChemAxon
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-MS (Non-derivatized) - 70eV, Positivesplash10-0bvl-3936000000-40f66fd593440074b89dView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0axr-3971400000-94938b1a7f02f2d7e3f3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f89-0029600000-cb620383d36ec5212616View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f89-0549200000-625c687632ff6518682aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-066r-3940000000-bc7f6c9b4bee36a96648View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0301900000-37a6323bf614a39086b7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01q9-0902200000-5b68a5b3289bba08e821View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-1159-1920000000-02625822db3358441b16View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
NameSMPDB/PathwhizKEGG
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
      Phenol Explorer Compound IDNot Available
      FoodDB 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 Compound59058967
      PDB IDNot Available
      ChEBI IDNot Available
      References
      Synthesis ReferenceNot Available
      Material Safety Data Sheet (MSDS)Not Available
      General ReferencesNot Available