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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2013-07-04 19:03:46 UTC
Update Date2018-05-20 20:30:40 UTC
HMDB IDHMDB0060856
Secondary Accession Numbers
  • HMDB60856
Metabolite Identification
Common NameO-Desmethyltramadol glucuronide
DescriptionO-Desmethyltramadol 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 Grnenthal GmbH in 1977 (Wikipedia).
Structure
Thumb
Synonyms
ValueSource
(2S,3S,4S,5R,6S)-6-{3-[(1R,2R)-2-[(dimethylamino)methyl]-1-hydroxycyclohexyl]phenoxy}-3,4,5-trihydroxyoxane-2-carboxylateHMDB
O-Desmethyl-tramadol glucuronideHMDB
(1R,2R)-O-Demethyl tramadol glucuronideCAS
(1R,2R)-O-Desmethyl tramadol glucuronideGenerator
(1R,2R)-O-Demethyltramadol glucuronideGenerator
(1R,2R)-O-Desmethyltramadol glucuronideGenerator
Chemical FormulaC21H31NO8
Average Molecular Weight425.478
Monoisotopic Molecular Weight425.204966962
IUPAC Name(2S,3S,4S,5R,6S)-6-{3-[(1R,2R)-2-[(dimethylamino)methyl]-1-hydroxycyclohexyl]phenoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
Traditional Name(2S,3S,4S,5R,6S)-6-{3-[(1R,2R)-2-[(dimethylamino)methyl]-1-hydroxycyclohexyl]phenoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
CAS Registry Number138921-77-4
SMILES
CN(C)C[C@H]1CCCC[C@]1(O)C1=CC(O[C@@H]2O[C@@H]([C@@H](O)[C@H](O)[C@H]2O)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)/t13-,15+,16+,17-,18+,20-,21+/m1/s1
InChI KeyDSBGQRZOJXSECT-VZFNFROLSA-N
Chemical Taxonomy
ClassificationNot classified
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 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
Polarizability43.84 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
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 ID62549482
      KEGG Compound IDNot Available
      BioCyc IDNot Available
      BiGG IDNot Available
      Wikipedia LinkNot Available
      METLIN IDNot Available
      PubChem Compound29919004
      PDB IDNot Available
      ChEBI IDNot Available
      References
      Synthesis ReferenceNot Available
      Material Safety Data Sheet (MSDS)Not Available
      General ReferencesNot Available