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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2013-07-04 18:54:46 UTC
Update Date2017-12-20 20:31:02 UTC
HMDB IDHMDB0060717
Secondary Accession Numbers
  • HMDB60717
Metabolite Identification
Common Name2-Hydroxy-imipramine glucuronide
Description2-Hydroxy-imipramine glucuronide is a metabolite of imipramine. Imipramine (sold as Antideprin, Deprimin, Deprinol, Depsol, Depsonil, Dynaprin, Eupramin, Imipramil, Irmin, Janimine, Melipramin, Surplix, Tofranil), also known as melipramine, is an antidepressant medication, a tricyclic antidepressant of the dibenzazepine group. Imipramine is mainly used in the treatment of major depression and enuresis (inability to control urination). It has also been evaluated for use in panic disorder. (Wikipedia)
Structure
Thumb
SynonymsNot Available
Chemical FormulaC25H32N2O7
Average Molecular Weight472.5308
Monoisotopic Molecular Weight472.220951388
IUPAC Name(2S,3S,4S,5R,6S)-6-({2-[3-(dimethylamino)propyl]-2-azatricyclo[9.4.0.0³,⁸]pentadeca-1(15),3,5,7,11,13-hexaen-6-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid
Traditional Name(2S,3S,4S,5R,6S)-6-({2-[3-(dimethylamino)propyl]-2-azatricyclo[9.4.0.0³,⁸]pentadeca-1(15),3,5,7,11,13-hexaen-6-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid
CAS Registry NumberNot Available
SMILES
CN(C)CCCN1C2=CC=CC=C2CCC2=CC(O[C@@H]3O[C@@H]([C@@H](O)[C@H](O)[C@H]3O)C(O)=O)=CC=C12
InChI Identifier
InChI=1S/C25H32N2O7/c1-26(2)12-5-13-27-18-7-4-3-6-15(18)8-9-16-14-17(10-11-19(16)27)33-25-22(30)20(28)21(29)23(34-25)24(31)32/h3-4,6-7,10-11,14,20-23,25,28-30H,5,8-9,12-13H2,1-2H3,(H,31,32)/t20-,21-,22+,23-,25+/m0/s1
InChI KeyCBEJFHYWZSCYSD-LYVDORBWSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as dibenzazepines. These are compounds with two benzene rings connected by an azepine ring. Azepine is an unsaturated seven-member heterocycle with one nitrogen atom replacing a carbon atom.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzazepines
Sub ClassDibenzazepines
Direct ParentDibenzazepines
Alternative Parents
Substituents
  • Dibenzazepine
  • Phenolic glycoside
  • 1-o-glucuronide
  • O-glucuronide
  • Glucuronic acid or derivatives
  • Hexose monosaccharide
  • Alkyldiarylamine
  • Glycosyl compound
  • O-glycosyl compound
  • Tertiary aliphatic/aromatic amine
  • Azepine
  • Beta-hydroxy acid
  • Hydroxy acid
  • Monosaccharide
  • Benzenoid
  • Oxane
  • Pyran
  • Amino acid or derivatives
  • Tertiary amine
  • Tertiary aliphatic amine
  • Secondary alcohol
  • Amino acid
  • Polyol
  • Oxacycle
  • Azacycle
  • Monocarboxylic acid or derivatives
  • Acetal
  • Carboxylic acid derivative
  • Carboxylic acid
  • Organooxygen compound
  • Organic nitrogen compound
  • Organic oxygen compound
  • Alcohol
  • Carbonyl group
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic oxide
  • Amine
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source:

Biological location:

Process

Naturally occurring process:

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 Solubility1.52 g/LALOGPS
logP2.25ALOGPS
logP-0.7ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)2.99ChemAxon
pKa (Strongest Basic)9.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area122.93 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity124.6 m³·mol⁻¹ChemAxon
Polarizability50.85 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, Positivesplash10-0a4i-9104200000-9ed61b9880f06db75172View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-00di-6141029000-c8ef9d1da7562ac875efView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052b-1090800000-af841a3c857a79c05923View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000t-1090000000-b017063a3c25681149d1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01p9-8390000000-c94d802c8c7a74eeed10View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00fs-1150900000-e02ed88b7be47823e273View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-1291300000-d5aba41c22b70ffbf153View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-06r2-3190000000-ae68d18e6190b658b545View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
Pathways
NameSMPDB/PathwhizKEGG
Imipramine Action PathwayThumbThumb?image type=greyscaleThumb?image type=simpleNot Available
Imipramine Metabolism PathwayThumbThumb?image type=greyscaleThumb?image type=simpleNot Available
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
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
      Phenol Explorer Compound 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 Compound10874382
      PDB IDNot Available
      ChEBI IDNot Available
      References
      Synthesis ReferenceNot Available
      Material Safety Data Sheet (MSDS)Not Available
      General ReferencesNot Available