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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2013-07-04 19:00:48 UTC
Update Date2017-12-07 18:05:00 UTC
HMDB IDHMDB0060808
Secondary Accession Numbers
  • HMDB60808
Metabolite Identification
Common NameAlpha-Hydroxy-tamoxifen-O-glucuronide
DescriptionAlpha-Hydroxy-tamoxifen-O-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 FormulaC32H37NO8
Average Molecular Weight563.6381
Monoisotopic Molecular Weight563.251917165
IUPAC Name(2S,3S,4S,5R,6S)-6-{[(2-{4-[(1Z)-1,2-diphenylbut-1-en-1-yl]phenoxy}ethyl)(methyl)amino]methoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
Traditional Name(2S,3S,4S,5R,6S)-6-{[(2-{4-[(1Z)-1,2-diphenylbut-1-en-1-yl]phenoxy}ethyl)(methyl)amino]methoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
CAS Registry NumberNot Available
SMILES
CC\C(=C(/C1=CC=CC=C1)C1=CC=C(OCCN(C)CO[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/C32H37NO8/c1-3-25(21-10-6-4-7-11-21)26(22-12-8-5-9-13-22)23-14-16-24(17-15-23)39-19-18-33(2)20-40-32-29(36)27(34)28(35)30(41-32)31(37)38/h4-17,27-30,32,34-36H,3,18-20H2,1-2H3,(H,37,38)/b26-25-/t27-,28-,29+,30-,32+/m0/s1
InChI KeyWEHJOAAYUBXOCR-RVJUPFJYSA-N
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-o-glucuronide
  • O-glucuronide
  • Diphenylmethane
  • Glucuronic acid or derivatives
  • Hexose monosaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • Phenylpropane
  • Phenoxy compound
  • Phenol ether
  • Alkyl aryl ether
  • Beta-hydroxy acid
  • Monocyclic benzene moiety
  • Benzenoid
  • Hydroxy acid
  • Monosaccharide
  • Oxane
  • Pyran
  • Secondary alcohol
  • Hemiaminal
  • Polyol
  • Oxacycle
  • Carboxylic acid derivative
  • Carboxylic acid
  • Acetal
  • Ether
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Organonitrogen compound
  • Organooxygen compound
  • Organic oxygen compound
  • Alcohol
  • Carbonyl group
  • Organic nitrogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organopnictogen 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 Solubility0.018 g/LALOGPS
logP4.04ALOGPS
logP1.8ChemAxon
logS-4.5ALOGPS
pKa (Strongest Acidic)3.22ChemAxon
pKa (Strongest Basic)6.38ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area128.92 ŲChemAxon
Rotatable Bond Count12ChemAxon
Refractivity161.81 m³·mol⁻¹ChemAxon
Polarizability61.17 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, Positivesplash10-0aba-9314230000-3b0bf901162c03a1dd26View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0ab9-9425105000-de068111fe0e93ca012dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-06rb-0228190000-ad93e0be10a4543f4b34View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0abi-3129000000-66973fd8f2db0c9cadedView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a59-8298000000-12d6372a632284dd6a3cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03xr-2232090000-20bc4fb5d943926b1befView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-4493050000-4d60b55e37cbfb833ca6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-06re-9543000000-35f47eaea0ed8a225523View in MoNA
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
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 IDDBMET00794
      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