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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2013-07-09 16:06:53 UTC
Update Date2019-07-23 07:15:21 UTC
HMDB IDHMDB0060913
Secondary Accession Numbers
  • HMDB0060983
  • HMDB0061072
  • HMDB60913
  • HMDB60983
  • HMDB61072
Metabolite Identification
Common NameZopiclone N-oxide
DescriptionZopiclone N-oxide is a primary, active metabolite of zopiclone. Zopiclone (brand names Imovane, Zimovane, and Dopareel) is a nonbenzodiazepine hypnotic agent used in the treatment of insomnia. Zopiclone is molecularly distinct from benzodiazepine drugs and belongs to the class of drugs known as cyclopyrrolones. However, zopiclone increases the normal transmission of the neurotransmitter gamma-aminobutyric acid (GABA) in the central nervous system, via modulating benzodiazepine receptors in the same way that benzodiazepine drugs do (Wikipedia).
Structure
Data?1563866121
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-oneHMDB
N-Oxide-zopicloneHMDB
N-OxidezopicloneHMDB
OXZOPHMDB
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 Number43200-96-0
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
Description belongs to the class of organic compounds known as cyclopyrrolones. Cyclopyrrolones are compounds belonging to a family of pyridin-2-ylpyrrole based chemicals. The pyrrole is usually fused to a benzene, pyrimidine, or dithiin.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyrrolopyrazines
Sub ClassCyclopyrrolones
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

Source:

Biological location:

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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-9613000000-d0e6375bc5d9e037ced2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0400900000-a5ebcf2c617173aece5aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01bc-3922100000-7f231f19478b63a44609Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fk9-9300000000-2cfa190b1972aa011ac1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0000900000-566ad044f64cf6cfa616Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0020900000-9e629e670388e31ec721Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fb9-9500000000-e25f37f0f0149f5ed631Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB 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 Compound162548
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available