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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2013-07-09 16:10:55 UTC
Update Date2017-12-07 18:33:29 UTC
HMDB IDHMDB0060983
Secondary Accession Numbers
  • HMDB60983
Metabolite Identification
Common Namezopiclone-N-oxide
Descriptionzopiclone-N-oxide is a metabolite of eszopiclone. Eszopiclone, marketed by Sepracor under the brand-name Lunesta, is a nonbenzodiazepine hypnotic used as a treatment for insomnia. Eszopiclone is the active dextrorotatory stereoisomer of zopiclone, and belongs to the class of drugs known as cyclopyrrolones. Eszopiclone is a short acting nonbenzodiazepine sedative hypnotic. (Wikipedia)
Structure
Thumb
Synonyms
ValueSource
6-(5-chloro-2-Pyridyl)-7-((4-oxo-4-methyl-1-piperazinyl)carbonyloxy)-6,7-dihydro(5H)pyrrolo(3,4-b)pyrazin-5-oneMeSH
N-Oxide-zopicloneMeSH
N-OxidezopicloneMeSH
OXZOPMeSH
Chemical FormulaC17H17ClN6O4
Average Molecular Weight404.808
Monoisotopic Molecular Weight404.099980769
IUPAC Name6-(5-chloropyridin-2-yl)-7-oxo-5H,6H,7H-pyrrolo[3,4-b]pyrazin-5-yl 1-methyl-1-oxo-1λ⁵-piperazine-4-carboxylate
Traditional Name6-(5-chloropyridin-2-yl)-7-oxo-5H-pyrrolo[3,4-b]pyrazin-5-yl 1-methyl-1-oxo-1λ⁵-piperazine-4-carboxylate
CAS Registry NumberNot Available
SMILES
CN1(=O)CCN(CC1)C(=O)OC1N(C(=O)C2=C1N=CC=N2)C1=NC=C(Cl)C=C1
InChI Identifier
InChI=1S/C17H17ClN6O4/c1-24(27)8-6-22(7-9-24)17(26)28-16-14-13(19-4-5-20-14)15(25)23(16)12-3-2-11(18)10-21-12/h2-5,10,16H,6-9H2,1H3
InChI KeyIPTIKKTXLHVRKN-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as cyclopyrrolones. These are compounds belonging to a family of pyridin-2-ylpyrrole based chemicals. The pyrrole is usually fused to a benzene, pyrimidine, or dithiin.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganoheterocyclic compounds
Sub ClassPyrrolopyrazines
Direct ParentCyclopyrrolones
Alternative Parents
Substituents
  • Cyclopyrrolone
  • Piperazine-1-carboxylic acid
  • 2-heteroaryl carboxamide
  • N-methylpiperazine
  • N-alkylpiperazine
  • Aryl chloride
  • Aryl halide
  • 1,4-diazinane
  • Piperazine
  • Pyrazine
  • Pyridine
  • Imidolactam
  • Trialkyl amine oxide
  • Carbamic acid ester
  • Tertiary carboxylic acid amide
  • Heteroaromatic compound
  • Carboxamide group
  • Lactam
  • Carbonic acid derivative
  • Trisubstituted n-oxide
  • Azacycle
  • Carboxylic acid derivative
  • N-oxide
  • Organopnictogen compound
  • Organohalogen compound
  • Organochloride
  • Organonitrogen compound
  • Organooxygen compound
  • Organic nitrogen compound
  • Organic oxide
  • Organic zwitterion
  • Organic oxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Organ and components:

Source:

Role

Biological role:

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 Solubility0.32 g/LALOGPS
logP-0.35ALOGPS
logP-0.32ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)13.04ChemAxon
pKa (Strongest Basic)2.68ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area115.4 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity97.93 m³·mol⁻¹ChemAxon
Polarizability38.65 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, Positivesplash10-000i-9613000000-d0e6375bc5d9e037ced2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0400900000-a5ebcf2c617173aece5aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01bc-3922100000-7f231f19478b63a44609View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fk9-9300000000-2cfa190b1972aa011ac1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0000900000-566ad044f64cf6cfa616View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0020900000-9e629e670388e31ec721View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fb9-9500000000-e25f37f0f0149f5ed631View 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
      DrugBank Metabolite IDDBMET00299
      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
      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