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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2013-06-12 17:32:05 UTC
Update Date2019-07-23 07:14:32 UTC
HMDB IDHMDB0060530
Secondary Accession Numbers
  • HMDB60530
Metabolite Identification
Common Name4-Hydroxytamoxifen
Description4-Hydroxytamoxifen, also known as 4-OHT or tamogel, belongs to the class of organic compounds 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. 4-Hydroxytamoxifen is a drug. 4-Hydroxytamoxifen is a very strong basic compound (based on its pKa). Within humans, 4-hydroxytamoxifen participates in a number of enzymatic reactions. In particular, 4-hydroxytamoxifen can be biosynthesized from tamoxifen through the action of the enzyme cytochrome P450 2D6. In addition, 4-hydroxytamoxifen and uridine diphosphate glucuronic acid can be converted into 4-hydroxytamoxifen-O-glucuronide and uridine 5'-diphosphate through its interaction with the enzyme UDP-glucuronosyltransferase 1-4. In humans, 4-hydroxytamoxifen is involved in tamoxifen metabolism pathway. 4-Hydroxytamoxifen is a potentially toxic compound.
Structure
Data?1563866072
Synonyms
ValueSource
4-MonohydroxytamoxifenChEBI
4-OHTChEBI
TamogelKegg
4-HYDROXYTAMOXIFENChEBI
4-Hydroxytamoxifen, (Z)-isomerMeSH
4oh-TamoxifenMeSH
AfimoxifeneMeSH
4-(1-(4-(2-(Dimethylamino)ethoxy)phenyl)-2-phenylbut-1-enyl)phenolMeSH
Tamoxifen metabolite bMeSH
4-OHT hydrotamoxifenMeSH
4-Hydroxy-tamoxifenMeSH
4-Hydroxytamoxifen, (e)-isomerMeSH
Para-hydroxytamoxifenMeSH
4'-HydroxytamoxifenMeSH
Chemical FormulaC26H29NO2
Average Molecular Weight387.514
Monoisotopic Molecular Weight387.219829177
IUPAC Name4-[(1Z)-1-{4-[2-(dimethylamino)ethoxy]phenyl}-2-phenylbut-1-en-1-yl]phenol
Traditional Name4-hydroxytamoxifen
CAS Registry NumberNot Available
SMILES
CC\C(=C(/C1=CC=C(O)C=C1)C1=CC=C(OCCN(C)C)C=C1)C1=CC=CC=C1
InChI Identifier
InChI=1S/C26H29NO2/c1-4-25(20-8-6-5-7-9-20)26(21-10-14-23(28)15-11-21)22-12-16-24(17-13-22)29-19-18-27(2)3/h5-17,28H,4,18-19H2,1-3H3/b26-25-
InChI KeyTXUZVZSFRXZGTL-QPLCGJKRSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds 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.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassStilbenes
Sub ClassNot Available
Direct ParentStilbenes
Alternative Parents
Substituents
  • Stilbene
  • Diphenylmethane
  • Phenylpropane
  • Phenoxy compound
  • Phenol ether
  • Alkyl aryl ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Tertiary aliphatic amine
  • Tertiary amine
  • Ether
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Amine
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

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 Solubility0.003 g/LALOGPS
logP5.44ALOGPS
logP5.69ChemAxon
logS-5.1ALOGPS
pKa (Strongest Acidic)9.45ChemAxon
pKa (Strongest Basic)8.66ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area32.7 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity130.41 m³·mol⁻¹ChemAxon
Polarizability45.22 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9134000000-776733ca504d7de5cabdSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0a4i-9104300000-0991f6db19bd6e1d5545Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0ads-3973000000-bb1382fca99270235a01Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0ads-3973000000-bb1382fca99270235a01Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-1239000000-84645e53e8de455443fbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-9455000000-9cfa2d15949946fc03c7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-9261000000-b6bb4e0b0330b5c146c1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0009000000-ae47347b1ffe098e2374Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014r-1019000000-a006c4264d6b4b3d156fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014j-5296000000-6a3ed7fb5ff7614b731aSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane (predicted from logP)
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 IDDB04468
      Phenol Explorer Compound IDNot Available
      FooDB IDNot Available
      KNApSAcK IDNot Available
      Chemspider ID395987
      KEGG Compound IDC05011
      BioCyc IDNot Available
      BiGG IDNot Available
      Wikipedia LinkAfimoxifene
      METLIN IDNot Available
      PubChem Compound449459
      PDB IDNot Available
      ChEBI ID44616
      Food Biomarker OntologyNot Available
      VMH IDNot Available
      References
      Synthesis ReferenceNot Available
      Material Safety Data Sheet (MSDS)Not Available
      General ReferencesNot Available