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Record Information
Version4.0
Creation Date2013-06-15 18:04:00 UTC
Update Date2017-09-27 08:43:51 UTC
HMDB IDHMDB0060616
Secondary Accession Numbers
  • HMDB60616
Metabolite Identification
Common NameTamoxifen-N-glucuronide
DescriptionTamoxifen-N-glucuronide is a metabolite of tamoxifen. Tamoxifen is an antagonist of the estrogen receptor in breast tissue via its active metabolite, hydroxytamoxifen. In other tissues such as the endometrium, it behaves as an agonist, and thus may be characterized as a mixed agonist/antagonist. Tamoxifen is the usual endocrine therapy for hormone receptor-positive breast cancer in pre-menopausal women, and is also a standard in post-menopausal women although aromatase inhibitors are also frequently used in that setting. (Wikipedia)
Structure
Thumb
Synonyms
ValueSource
Tamoxifen N-glucuronideChEBI
Tamoxifen N-b-D-glucosiduronateGenerator
Tamoxifen N-b-D-glucosiduronic acidGenerator
Tamoxifen N-beta-D-glucosiduronateGenerator
Tamoxifen N-β-D-glucosiduronateGenerator
Tamoxifen N-β-D-glucosiduronic acidGenerator
Chemical FormulaC32H38NO7
Average Molecular Weight548.6466
Monoisotopic Molecular Weight548.264827575
IUPAC Name(2R,3R,4S,5S,6S)-6-carboxy-N-(2-{4-[(1Z)-1,2-diphenylbut-1-en-1-yl]phenoxy}ethyl)-3,4,5-trihydroxy-N,N-dimethyloxan-2-aminium
Traditional Nametamoxifen N-glucuronide
CAS Registry NumberNot Available
SMILES
CC\C(=C(/C1=CC=CC=C1)C1=CC=C(OCC[N+](C)(C)[C@@H]2O[C@@H]([C@@H](O)[C@H](O)[C@H]2O)C(O)=O)C=C1)C1=CC=CC=C1
InChI Identifier
InChI=1S/C32H37NO7/c1-4-25(21-11-7-5-8-12-21)26(22-13-9-6-10-14-22)23-15-17-24(18-16-23)39-20-19-33(2,3)31-29(36)27(34)28(35)30(40-31)32(37)38/h5-18,27-31,34-36H,4,19-20H2,1-3H3/p+1/b26-25-/t27-,28-,29+,30-,31+/m0/s1
InChI KeyUKFQQYJAYUAYES-DTMHFWPESA-O
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as stilbene glycosides. These are compounds structurally characterized by the presence of a carbohydrate moiety glycosidically linked to the stilbene skeleton.
KingdomChemical entities
Super ClassOrganic compounds
ClassPhenylpropanoids and polyketides
Sub ClassStilbenes
Direct ParentStilbene glycosides
Alternative Parents
Substituents
  • Stilbene glycoside
  • 1-n-glucuronide
  • N-glucuronide
  • Diphenylmethane
  • Glucuronic acid or derivatives
  • Glycosyl compound
  • N-glycosyl compound
  • Phenylpropane
  • Phenoxy compound
  • Phenol ether
  • Alkyl aryl ether
  • Beta-hydroxy acid
  • Monocyclic benzene moiety
  • Oxane
  • Benzenoid
  • Hydroxy acid
  • Pyran
  • Tetraalkylammonium salt
  • Hemiaminal
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Ether
  • Oxacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Polyol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organic salt
  • Carbonyl group
  • Alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Organic cation
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
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 Solubility0.0029 g/LALOGPS
logP2.46ALOGPS
logP0.095ChemAxon
logS-5.3ALOGPS
pKa (Strongest Acidic)3.18ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area116.45 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity171.87 m³·mol⁻¹ChemAxon
Polarizability59.48 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, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
Pathways
NameSMPDB/PathwhizKEGG
Tamoxifen Metabolism PathwayPw000582Pw000582 greyscalePw000582 simpleNot Available
Tamoxifen PathwayPw000250Pw000250 greyscalePw000250 simpleNot Available
Displaying all 2 entries
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 IDDBMET01004
      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 Compound5460873
      PDB IDNot Available
      ChEBI ID32663
      References
      Synthesis ReferenceNot Available
      Material Safety Data Sheet (MSDS)Not Available
      General ReferencesNot Available