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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2013-06-15 18:11:19 UTC
Update Date2017-12-07 17:32:05 UTC
HMDB IDHMDB0060629
Secondary Accession Numbers
  • HMDB60629
Metabolite Identification
Common NameHydroxydesmthyl doxepin glucuronide
DescriptionHydroxydesmthyl doxepin glucuronide is a metabolite of doxepin. Doxepin is a psychotropic agent with tricyclic antidepressant and anxiolytic properties, known under many brand-names such as Aponal, the original preparation by Boehringer-Mannheim, now part of the Roche group; Adapine, Doxal, Deptran, Sinquan and Sinequan. As doxepin hydrochloride, it is the active ingredient in cream-based preparations (Zonalon and Xepin) for the treatment of dermatological itch. (Wikipedia)
Structure
Thumb
SynonymsNot Available
Chemical FormulaC25H29NO8
Average Molecular Weight471.4997
Monoisotopic Molecular Weight471.189316909
IUPAC Name6-{[(2E)-2-[3-(dimethylamino)propylidene]-9-oxatricyclo[9.4.0.0³,⁸]pentadeca-1(11),3(8),4,6,12,14-hexaen-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
Traditional Name6-{[(2E)-2-[3-(dimethylamino)propylidene]-9-oxatricyclo[9.4.0.0³,⁸]pentadeca-1(11),3(8),4,6,12,14-hexaen-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
CAS Registry NumberNot Available
SMILES
CN(C)CC\C=C1/C2=C(COC3=C1C=C(OC1OC(C(O)C(O)C1O)C(O)=O)C=C3)C=CC=C2
InChI Identifier
InChI=1S/C25H29NO8/c1-26(2)11-5-8-17-16-7-4-3-6-14(16)13-32-19-10-9-15(12-18(17)19)33-25-22(29)20(27)21(28)23(34-25)24(30)31/h3-4,6-10,12,20-23,25,27-29H,5,11,13H2,1-2H3,(H,30,31)/b17-8+
InChI KeyRECOUBTVNVWWDB-CAOOACKPSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as dibenzoxepines. These are compounds containing a dibenzoxepine moiety, which consists of two benzene connected by an oxazepine ring.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganoheterocyclic compounds
Sub ClassBenzoxepines
Direct ParentDibenzoxepines
Alternative Parents
Substituents
  • Dibenzoxepine
  • Phenolic glycoside
  • 1-o-glucuronide
  • O-glucuronide
  • Glucuronic acid or derivatives
  • Hexose monosaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • Alkyl aryl ether
  • Beta-hydroxy acid
  • Hydroxy acid
  • Benzenoid
  • Monosaccharide
  • Pyran
  • Oxane
  • Amino acid or derivatives
  • Amino acid
  • Tertiary aliphatic amine
  • Tertiary amine
  • Secondary alcohol
  • Polyol
  • Monocarboxylic acid or derivatives
  • Oxacycle
  • Acetal
  • Carboxylic acid derivative
  • Carboxylic acid
  • Ether
  • Organooxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Alcohol
  • Carbonyl group
  • Organic oxygen compound
  • Amine
  • Hydrocarbon derivative
  • Organic nitrogen 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 Solubility0.45 g/LALOGPS
logP1.84ALOGPS
logP-1.1ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)2.7ChemAxon
pKa (Strongest Basic)9.76ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area128.92 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity132.24 m³·mol⁻¹ChemAxon
Polarizability48.97 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-9104200000-45cfe30b22a906bdd0c5View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-00di-9152037000-6df8bbf545417cdd2d18View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f6t-0090800000-09b12b174469f3725e34View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000t-1090000000-f6a1bef96ec53447fe0fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-06xt-4290000000-d4cb7c0c32d7f6657d31View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00dl-1140900000-71b2dc18f01f3c87dc79View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-2290300000-a4ba36b88b02e88ce14cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01ox-3190000000-a23274c9b76642fb358aView in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
Pathways
NameSMPDB/PathwhizKEGG
Doxepin Metabolism PathwayPw000617Pw000617 greyscalePw000617 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 IDDBMET00879
      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