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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2013-07-04 18:54:41 UTC
Update Date2017-12-07 17:48:29 UTC
HMDB IDHMDB0060716
Secondary Accession Numbers
  • HMDB60716
Metabolite Identification
Common Name2-Hydroxy-desipramine glucuronide
Description2-Hydroxy-desipramine glucuronide is a metabolite of desipramine. Desipramine (also known as desmethylimipramine) is a tricyclic antidepressant (TCA). It inhibits the reuptake of norepinephrine and to a lesser extent serotonin. It is used to treat depression, but not considered a first line treatment since the introduction of SSRI antidepressants. Desipramine is an active metabolite of imipramine. It is sold under the brand names Norpramin and Pertofane. Along with other tricyclics, desipramine has found use in treating neuropathic pain. (Wikipedia)
Structure
Thumb
SynonymsNot Available
Chemical FormulaC24H30N2O7
Average Molecular Weight458.5042
Monoisotopic Molecular Weight458.205301324
IUPAC Name(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-({2-[3-(methylamino)propyl]-2-azatricyclo[9.4.0.0³,⁸]pentadeca-1(15),3,5,7,11,13-hexaen-6-yl}oxy)oxane-2-carboxylic acid
Traditional Name(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-({2-[3-(methylamino)propyl]-2-azatricyclo[9.4.0.0³,⁸]pentadeca-1(15),3,5,7,11,13-hexaen-6-yl}oxy)oxane-2-carboxylic acid
CAS Registry NumberNot Available
SMILES
CNCCCN1C2=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/C24H30N2O7/c1-25-11-4-12-26-17-6-3-2-5-14(17)7-8-15-13-16(9-10-18(15)26)32-24-21(29)19(27)20(28)22(33-24)23(30)31/h2-3,5-6,9-10,13,19-22,24-25,27-29H,4,7-8,11-12H2,1H3,(H,30,31)/t19-,20-,21+,22-,24+/m0/s1
InChI KeyXJHAOJJEVSPMBA-QMDPOKHVSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities 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.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganoheterocyclic compounds
Sub ClassBenzazepines
Direct ParentDibenzazepines
Alternative Parents
Substituents
  • Dibenzazepine
  • Phenolic glycoside
  • O-glucuronide
  • 1-o-glucuronide
  • Glucuronic acid or derivatives
  • Alkyldiarylamine
  • O-glycosyl compound
  • Glycosyl compound
  • Tertiary aliphatic/aromatic amine
  • Azepine
  • Beta-hydroxy acid
  • Hydroxy acid
  • Benzenoid
  • Oxane
  • Monosaccharide
  • Pyran
  • Secondary alcohol
  • Tertiary amine
  • Amino acid
  • Amino acid or derivatives
  • Acetal
  • Carboxylic acid derivative
  • Carboxylic acid
  • Secondary aliphatic amine
  • Oxacycle
  • Azacycle
  • Monocarboxylic acid or derivatives
  • Secondary amine
  • Polyol
  • Organic nitrogen compound
  • Amine
  • Organic oxide
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organopnictogen compound
  • Carbonyl group
  • Alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

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 Solubility1.76 g/LALOGPS
logP0.58ALOGPS
logP-0.83ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)3ChemAxon
pKa (Strongest Basic)10.02ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area131.72 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity119.3 m³·mol⁻¹ChemAxon
Polarizability48.99 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, Positivesplash10-0006-9105200000-d2db567f92dbadc1b20bView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0cdu-5141029000-44756ec23ac770826fbcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-053u-0090800000-dfb62862c2a3aa2b1cfbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00lr-1090000000-665debebaa2776c55010View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-02mi-6290000000-f17840bb2ddd309f0bcfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0bu0-1150900000-7111804e3c310327e28fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-2291200000-e80d2b2af057e310b1bcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-06si-3190000000-648d96c296a9cd2e104eView in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
Pathways
NameSMPDB/PathwhizKEGG
Desipramine Metabolism PathwayPw000602Pw000602 greyscalePw000602 simpleNot Available
Desipramine PathwayPw000425Pw000425 greyscalePw000425 simpleNot Available
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 IDDBMET00679
      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