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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2013-07-04 19:03:46 UTC
Update Date2017-12-07 18:14:36 UTC
HMDB IDHMDB0060856
Secondary Accession Numbers
  • HMDB60856
Metabolite Identification
Common NameO-Desmethyl-tramado glucuronide
DescriptionO-Desmethyl-tramado glucuronide is a metabolite of tramadol. Tramadol hydrochloride (trademarked as Conzip, Ryzolt, Ultracet, Ultram in the USA,Ralivia and Zytram XL in Canada) is a centrally-acting synthetic analgesic used to treat moderate to moderately-severe pain. The drug has a wide range of applications, including treatment of rheumatoid arthritis, restless legs syndrome and fibromyalgia. It was launched and marketed as Tramal by the German pharmaceutical company Grünenthal GmbH in 1977. (Wikipedia)
Structure
Thumb
SynonymsNot Available
Chemical FormulaC21H31NO8
Average Molecular Weight425.4727
Monoisotopic Molecular Weight425.204966973
IUPAC Name6-(3-{2-[(dimethylamino)methyl]-1-hydroxycyclohexyl}phenoxy)-3,4,5-trihydroxyoxane-2-carboxylic acid
Traditional Name6-(3-{2-[(dimethylamino)methyl]-1-hydroxycyclohexyl}phenoxy)-3,4,5-trihydroxyoxane-2-carboxylic acid
CAS Registry NumberNot Available
SMILES
CN(C)CC1CCCCC1(O)C1=CC(OC2OC(C(O)C(O)C2O)C(O)=O)=CC=C1
InChI Identifier
InChI=1S/C21H31NO8/c1-22(2)11-13-6-3-4-9-21(13,28)12-7-5-8-14(10-12)29-20-17(25)15(23)16(24)18(30-20)19(26)27/h5,7-8,10,13,15-18,20,23-25,28H,3-4,6,9,11H2,1-2H3,(H,26,27)
InChI KeyDSBGQRZOJXSECT-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic oxygen compounds
Sub ClassOrganooxygen compounds
Direct ParentPhenolic glycosides
Alternative Parents
Substituents
  • Phenolic glycoside
  • 1-o-glucuronide
  • O-glucuronide
  • Glucuronic acid or derivatives
  • Hexose monosaccharide
  • O-glycosyl compound
  • Phenoxy compound
  • Phenol ether
  • Aralkylamine
  • Beta-hydroxy acid
  • Cyclohexanol
  • Benzenoid
  • Pyran
  • Oxane
  • Hydroxy acid
  • Monocyclic benzene moiety
  • Monosaccharide
  • Tertiary alcohol
  • Cyclic alcohol
  • Amino acid
  • Tertiary aliphatic amine
  • Tertiary amine
  • Secondary alcohol
  • Amino acid or derivatives
  • Acetal
  • Carboxylic acid derivative
  • Carboxylic acid
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Monocarboxylic acid or derivatives
  • Alcohol
  • Carbonyl group
  • Amine
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organonitrogen compound
  • Organic oxide
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic 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 Solubility4.6 g/LALOGPS
logP0.51ALOGPS
logP-2.4ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)2.81ChemAxon
pKa (Strongest Basic)9.23ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area139.92 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity105.8 m³·mol⁻¹ChemAxon
Polarizability43.4 ųChemAxon
Number of Rings3ChemAxon
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-9116200000-11f2c539f91ef287199eView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-05di-8512069000-1ffac14b758f75562b68View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0pc0-0093700000-4c45416764dabe146eecView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0190000000-48e1fb0cc140289f87f3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0kai-8390000000-5306fe921d395fcd08b8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00ea-2264900000-edab78d48b3f967afd53View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000t-2392100000-a2ebce97f564f27c0a4bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000t-5390000000-0b86fe799c41c053203dView in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
Pathways
NameSMPDB/PathwhizKEGG
Tramadol Metabolism PathwayPw000613Pw000613 greyscalePw000613 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 IDDBMET00966
      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