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Record Information
Version3.6
Creation Date2013-07-09 16:18:56 UTC
Update Date2016-02-11 08:18:36 UTC
HMDB IDHMDB61107
Secondary Accession NumbersNone
Metabolite Identification
Common NameBuspirone N-oxide
DescriptionBuspirone N-oxide 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-[1-oxo-4-(pyrimidin-2-yl)-1λ⁵-piperazin-1-yl]butyl}-8-azaspiro[4.5]decane-7,9-dione
Traditional Name8-{4-[1-oxo-4-(pyrimidin-2-yl)-1λ⁵-piperazin-1-yl]butyl}-8-azaspiro[4.5]decane-7,9-dione
CAS Registry NumberNot Available
SMILES
O=C1CC2(CCCC2)CC(=O)N1CCCCN1(=O)CCN(CC1)C1=NC=CC=N1
InChI Identifier
InChI=1S/C21H31N5O3/c27-18-16-21(6-1-2-7-21)17-19(28)25(18)10-3-4-13-26(29)14-11-24(12-15-26)20-22-8-5-9-23-20/h5,8-9H,1-4,6-7,10-17H2
InChI KeyInChIKey=PXFOIYSPRVISSG-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
  • N-arylpiperazine
  • Azaspirodecanedione
  • Azaspirodecane
  • Dialkylarylamine
  • Piperidinedione
  • N-alkylpiperazine
  • Piperidinone
  • Dicarboximide
  • Delta-lactam
  • Pyrimidine
  • Piperidine
  • Carboxylic acid imide, n-substituted
  • Heteroaromatic compound
  • Carboxylic acid imide
  • Tertiary amine
  • Lactam
  • Carboxamide group
  • Azacycle
  • Trisubstituted n-oxide
  • Carboxylic acid derivative
  • N-oxide
  • Hydrocarbon derivative
  • Organic salt
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Organic cation
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic 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 Solubility0.39 mg/mLALOGPS
logP0.4ALOGPS
logP0.65ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)19.26ChemAxon
pKa (Strongest Basic)1.89ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area93.28 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity110.94 m3·mol-1ChemAxon
Polarizability44.32 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 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 IDDBMET00477
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 LinkHMDB61107
Metagene LinkHMDB61107
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