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Record Information
Version4.0
Creation Date2013-07-09 16:17:21 UTC
Update Date2017-09-27 08:44:01 UTC
HMDB IDHMDB0061085
Secondary Accession Numbers
  • HMDB61085
Metabolite Identification
Common Namealpha-Hydroxy-N-desmethyl-tamoxifen
Descriptionalpha-Hydroxy-N-desmethyl-tamoxifen 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 FormulaC25H27NO2
Average Molecular Weight373.4874
Monoisotopic Molecular Weight373.204179113
IUPAC Name(2R,3E)-4-{4-[2-(methylamino)ethoxy]phenyl}-3,4-diphenylbut-3-en-2-ol
Traditional Name(2R,3E)-4-{4-[2-(methylamino)ethoxy]phenyl}-3,4-diphenylbut-3-en-2-ol
CAS Registry NumberNot Available
SMILES
CNCCOC1=CC=C(C=C1)C(=C(\[C@@H](C)O)C1=CC=CC=C1)\C1=CC=CC=C1
InChI Identifier
InChI=1S/C25H27NO2/c1-19(27)24(20-9-5-3-6-10-20)25(21-11-7-4-8-12-21)22-13-15-23(16-14-22)28-18-17-26-2/h3-16,19,26-27H,17-18H2,1-2H3/b25-24-/t19-/m1/s1
InChI KeyGREXPZNIZPCGIV-KRXRYSOXSA-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
  • Cinnamyl alcohol
  • Phenylpropane
  • Phenoxy compound
  • Phenol ether
  • Alkyl aryl ether
  • Monocyclic benzene moiety
  • Benzenoid
  • Secondary alcohol
  • Secondary amine
  • Ether
  • Secondary aliphatic amine
  • Organopnictogen compound
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Alcohol
  • Organic nitrogen compound
  • Amine
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic 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 Solubility0.0014 g/LALOGPS
logP4.82ALOGPS
logP4.66ChemAxon
logS-5.4ALOGPS
pKa (Strongest Acidic)14.8ChemAxon
pKa (Strongest Basic)9.51ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area41.49 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity124.73 m³·mol⁻¹ChemAxon
Polarizability43.09 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, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ab9-1049000000-fa179e1fc4cb9d8b5b05View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9276000000-6ba9741bb3c7ad960409View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0537-9182000000-345aee5668b27c53461fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0009000000-8d280950bd0bc575fe27View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00xs-1049000000-6a22be13943fc2015cf0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-06ej-4293000000-f8a5b26e68804f3e0bd7View 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
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 IDDBMET00440
      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