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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-07-09 16:09:20 UTC
Update Date2021-09-14 15:47:16 UTC
HMDB IDHMDB0060955
Secondary Accession Numbers
  • HMDB60955
Metabolite Identification
Common Namemirtazapine-N-oxide
Descriptionmirtazapine-N-oxide is a metabolite of mirtazapine. Mirtazapine (Remeron, Avanza, Zispin) is a noradrenergic and specific serotonergic antidepressant (NaSSA) which was introduced by Organon International in the United States in 1990 and is used primarily in the treatment of depression. It is also commonly used as an anxiolytic, hypnotic, antiemetic, and appetite stimulant. Structurally, mirtazapine can also be classified as a tetracyclic antidepressant (TeCA). (Wikipedia)
Structure
Data?1563866127
SynonymsNot Available
Chemical FormulaC17H19N3O
Average Molecular Weight281.3523
Monoisotopic Molecular Weight281.152812245
IUPAC Name5-methyl-2,5λ⁵,19-triazatetracyclo[13.4.0.0²,⁷.0⁸,¹³]nonadeca-1(15),8,10,12,16,18-hexaen-5-one
Traditional Name5-methyl-2,5λ⁵,19-triazatetracyclo[13.4.0.0²,⁷.0⁸,¹³]nonadeca-1(15),8,10,12,16,18-hexaen-5-one
CAS Registry NumberNot Available
SMILES
CN1(=O)CCN2C(C1)C1=CC=CC=C1CC1=C2N=CC=C1
InChI Identifier
InChI=1S/C17H19N3O/c1-20(21)10-9-19-16(12-20)15-7-3-2-5-13(15)11-14-6-4-8-18-17(14)19/h2-8,16H,9-12H2,1H3
InChI KeyGAFCUVMEBFTFQJ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as piperazinoazepines. Piperazinoazepines are compounds containing a piperazinoazepine skeleton, which consists of an azepine ring fused to a piperazine.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPiperazinoazepines
Sub ClassNot Available
Direct ParentPiperazinoazepines
Alternative Parents
Substituents
  • Benzazepine
  • Piperazino-azepine
  • Dialkylarylamine
  • Azepine
  • N-methylpiperazine
  • N-alkylpiperazine
  • 1,4-diazinane
  • Piperazine
  • Pyridine
  • Imidolactam
  • Benzenoid
  • Trialkyl amine oxide
  • Heteroaromatic compound
  • Trisubstituted n-oxide
  • N-oxide
  • Azacycle
  • Hydrocarbon derivative
  • Organic oxide
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • 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 Solubility1.47 g/LALOGPS
logP-0.14ALOGPS
logP2.08ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)19.27ChemAxon
pKa (Strongest Basic)4.48ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area43.01 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity84.7 m³·mol⁻¹ChemAxon
Polarizability30.91 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
DarkChem[M+H]+166.57931661259
DarkChem[M-H]-165.05131661259
DeepCCS[M+H]+161.97330932474
DeepCCS[M-H]-159.61530932474
DeepCCS[M-2H]-192.52630932474
DeepCCS[M+Na]+168.06630932474
AllCCS[M+H]+165.732859911
AllCCS[M+H-H2O]+162.032859911
AllCCS[M+NH4]+169.132859911
AllCCS[M+Na]+170.132859911
AllCCS[M-H]-174.132859911
AllCCS[M+Na-2H]-173.632859911
AllCCS[M+HCOO]-173.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
mirtazapine-N-oxideCN1(=O)CCN2C(C1)C1=CC=CC=C1CC1=C2N=CC=C13646.8Standard polar33892256
mirtazapine-N-oxideCN1(=O)CCN2C(C1)C1=CC=CC=C1CC1=C2N=CC=C11795.7Standard non polar33892256
mirtazapine-N-oxideCN1(=O)CCN2C(C1)C1=CC=CC=C1CC1=C2N=CC=C12446.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - mirtazapine-N-oxide GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-0190000000-c5738c2f4bba6b1ecd542017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - mirtazapine-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 - mirtazapine-N-oxide 10V, Positive-QTOFsplash10-001i-0090000000-95879bc06c39ec337a9a2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - mirtazapine-N-oxide 20V, Positive-QTOFsplash10-053r-0090000000-9722155e1667fbf7ee422017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - mirtazapine-N-oxide 40V, Positive-QTOFsplash10-0aor-3690000000-4982de8694aa2b3ea8572017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - mirtazapine-N-oxide 10V, Negative-QTOFsplash10-001i-0090000000-ec845f4c09260c776b152017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - mirtazapine-N-oxide 20V, Negative-QTOFsplash10-0006-0920000000-466bd51f6b8616f20e382017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - mirtazapine-N-oxide 40V, Negative-QTOFsplash10-052f-0920000000-b4c213c1aeb988e8f1012017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - mirtazapine-N-oxide 10V, Positive-QTOFsplash10-001i-0090000000-0db20202647f4f8a9de62021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - mirtazapine-N-oxide 20V, Positive-QTOFsplash10-01q9-0090000000-2a2b7e34a89f0c935aa62021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - mirtazapine-N-oxide 40V, Positive-QTOFsplash10-00kb-0890000000-1b1f77be34c3a164de5c2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - mirtazapine-N-oxide 10V, Negative-QTOFsplash10-001i-0090000000-18e93f9625f62017f8e62021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - mirtazapine-N-oxide 20V, Negative-QTOFsplash10-001i-0090000000-18e93f9625f62017f8e62021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - mirtazapine-N-oxide 40V, Negative-QTOFsplash10-001i-0090000000-18e93f9625f62017f8e62021-09-22Wishart 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
  • Membrane (predicted from logP)
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 Compound46782381
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