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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2013-07-22 19:49:21 UTC
Update Date2017-10-23 19:15:53 UTC
HMDB IDHMDB0061124
Secondary Accession Numbers
  • HMDB61124
Metabolite Identification
Common Name4-Hydroxytamoxifen-N-glucuronide
Description4-Hydroxytamoxifen-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
SynonymsNot Available
Chemical FormulaC30H33NO9
Average Molecular Weight551.5843
Monoisotopic Molecular Weight551.215531659
IUPAC Name(2R,3R,4R,5S)-3,4,5-trihydroxy-6-{[(2-{4-[(1E)-1-(4-hydroxyphenyl)-2-phenylbut-1-en-1-yl]phenoxy}ethyl)amino]oxy}oxane-2-carboxylic acid
Traditional Name(2R,3R,4R,5S)-3,4,5-trihydroxy-6-{[(2-{4-[(1E)-1-(4-hydroxyphenyl)-2-phenylbut-1-en-1-yl]phenoxy}ethyl)amino]oxy}oxane-2-carboxylic acid
CAS Registry NumberNot Available
SMILES
CC\C(=C(\C1=CC=C(O)C=C1)C1=CC=C(OCCNOC2O[C@H]([C@H](O)[C@@H](O)[C@@H]2O)C(O)=O)C=C1)C1=CC=CC=C1
InChI Identifier
InChI=1S/C30H33NO9/c1-2-23(18-6-4-3-5-7-18)24(19-8-12-21(32)13-9-19)20-10-14-22(15-11-20)38-17-16-31-40-30-27(35)25(33)26(34)28(39-30)29(36)37/h3-15,25-28,30-35H,2,16-17H2,1H3,(H,36,37)/b24-23+/t25-,26-,27+,28-,30?/m1/s1
InChI KeyZGQCEPMGLPXICX-JMQJMEEHSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids.
KingdomChemical entities
Super ClassOrganic compounds
ClassPhenylpropanoids and polyketides
Sub ClassStilbenes
Direct ParentStilbenes
Alternative Parents
Substituents
  • Stilbene
  • Diphenylmethane
  • Glucuronic acid or derivatives
  • Phenylpropane
  • Phenoxy compound
  • Phenol ether
  • Beta-hydroxy acid
  • Alkyl aryl ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Monocyclic benzene moiety
  • Hydroxy acid
  • Monosaccharide
  • Benzenoid
  • Oxane
  • Pyran
  • Secondary alcohol
  • Oxacycle
  • Carboxylic acid derivative
  • Carboxylic acid
  • Ether
  • N-organohydroxylamine
  • Monocarboxylic acid or derivatives
  • Organoheterocyclic compound
  • Polyol
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Alcohol
  • Organopnictogen compound
  • Carbonyl group
  • Organic oxide
  • Organonitrogen compound
  • Organooxygen compound
  • Organic oxygen compound
  • 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 Solubility0.033 g/LALOGPS
logP3.42ALOGPS
logP2.07ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)2.93ChemAxon
pKa (Strongest Basic)4.37ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area157.94 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity164.61 m³·mol⁻¹ChemAxon
Polarizability58.53 ųChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
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, Positivesplash10-0ac3-9211340000-bc26513c0b5eef0d3323View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-001r-8160139000-0f6fad71d4ad44cc501eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f89-0412190000-11b6ac037236185e1e04View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05po-4679160000-05d31f671eb1f9c2f4e3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a71-6931000000-1b698d8ce9e1dcef3bf0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0zfr-1217190000-cad315c3931be2b7700fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0aor-2209020000-5dd0b4ad0b1af56e15b8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0aor-9203000000-e25864383872030891acView in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
Pathways
NameSMPDB/PathwhizKEGG
Tamoxifen Metabolism PathwayPw000582Pw000582 greyscalePw000582 simpleNot Available
Tamoxifen PathwayPw000250Pw000250 greyscalePw000250 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 IDDBMET00738
      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