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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-07-09 16:06:53 UTC
Update Date2021-09-14 14:58:08 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
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+187.16430932474
DeepCCS[M-H]-184.80630932474
DeepCCS[M-2H]-218.93830932474
DeepCCS[M+Na]+194.15730932474
AllCCS[M+H]+188.932859911
AllCCS[M+H-H2O]+186.332859911
AllCCS[M+NH4]+191.332859911
AllCCS[M+Na]+192.032859911
AllCCS[M-H]-187.932859911
AllCCS[M+Na-2H]-187.832859911
AllCCS[M+HCOO]-187.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Zopiclone N-oxideCN1(=O)CCN(CC1)C(=O)OC1N(C(=O)C2=C1N=CC=N2)C1=NC=C(Cl)C=C14031.9Standard polar33892256
Zopiclone N-oxideCN1(=O)CCN(CC1)C(=O)OC1N(C(=O)C2=C1N=CC=N2)C1=NC=C(Cl)C=C12740.1Standard non polar33892256
Zopiclone N-oxideCN1(=O)CCN(CC1)C(=O)OC1N(C(=O)C2=C1N=CC=N2)C1=NC=C(Cl)C=C13230.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Zopiclone N-oxide GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-9613000000-d0e6375bc5d9e037ced22017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Zopiclone N-oxide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Zopiclone N-oxide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Zopiclone N-oxide 10V, Positive-QTOFsplash10-0a4i-0400900000-a5ebcf2c617173aece5a2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Zopiclone N-oxide 20V, Positive-QTOFsplash10-01bc-3922100000-7f231f19478b63a446092017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Zopiclone N-oxide 40V, Positive-QTOFsplash10-0fk9-9300000000-2cfa190b1972aa011ac12017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Zopiclone N-oxide 10V, Negative-QTOFsplash10-0udi-0000900000-566ad044f64cf6cfa6162017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Zopiclone N-oxide 20V, Negative-QTOFsplash10-0udi-0020900000-9e629e670388e31ec7212017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Zopiclone N-oxide 40V, Negative-QTOFsplash10-0fb9-9500000000-e25f37f0f0149f5ed6312017-10-06Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
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 IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available