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Record Information
Version5.0
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 which is used for the potential treatment of menstrual-cycle related mastalgia, fibrocystic breast disease, breast disease, gynecomastia and keloid scarring. 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; which is mediated by the enzyme UDP-glucuronosyltransferase 1-4. In humans, 4-hydroxytamoxifen is involved in tamoxifen action pathway. 4-Hydroxytamoxifen is a potentially toxic compound.
Structure
Data?1563866072
Synonyms
ValueSource
4-MonohydroxytamoxifenChEBI
4-OHTChEBI
TamogelKegg
4-Hydroxytamoxifen, (Z)-isomerHMDB
4oh-TamoxifenHMDB
AfimoxifeneHMDB
4-(1-(4-(2-(Dimethylamino)ethoxy)phenyl)-2-phenylbut-1-enyl)phenolHMDB
Tamoxifen metabolite bHMDB
4-OHT hydrotamoxifenHMDB
4-Hydroxy-tamoxifenHMDB
4-Hydroxytamoxifen, (e)-isomerHMDB
Para-hydroxytamoxifenHMDB
4'-HydroxytamoxifenHMDB
4-HYDROXYTAMOXIFENChEBI
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

Biological location

Process

Naturally occurring process

Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+195.73831661259
DarkChem[M-H]-190.41231661259
DeepCCS[M+H]+199.79130932474
DeepCCS[M-H]-197.43330932474
DeepCCS[M-2H]-231.09630932474
DeepCCS[M+Na]+206.32430932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
4-HydroxytamoxifenCC\C(=C(/C1=CC=C(O)C=C1)C1=CC=C(OCCN(C)C)C=C1)C1=CC=CC=C14148.1Standard polar33892256
4-HydroxytamoxifenCC\C(=C(/C1=CC=C(O)C=C1)C1=CC=C(OCCN(C)C)C=C1)C1=CC=CC=C12772.7Standard non polar33892256
4-HydroxytamoxifenCC\C(=C(/C1=CC=C(O)C=C1)C1=CC=C(OCCN(C)C)C=C1)C1=CC=CC=C13025.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
4-Hydroxytamoxifen,1TMS,isomer #1CC/C(=C(/C1=CC=C(OCCN(C)C)C=C1)C1=CC=C(O[Si](C)(C)C)C=C1)C1=CC=CC=C13355.4Semi standard non polar33892256
4-Hydroxytamoxifen,1TBDMS,isomer #1CC/C(=C(/C1=CC=C(OCCN(C)C)C=C1)C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)C1=CC=CC=C13558.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 4-Hydroxytamoxifen GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9134000000-776733ca504d7de5cabd2017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Hydroxytamoxifen GC-MS (1 TMS) - 70eV, Positivesplash10-0a4i-9104300000-0991f6db19bd6e1d55452017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Hydroxytamoxifen GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Hydroxytamoxifen GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Hydroxytamoxifen LC-ESI-qTof , Positive-QTOFsplash10-0ads-3973000000-bb1382fca99270235a012017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Hydroxytamoxifen , positive-QTOFsplash10-0ads-3973000000-bb1382fca99270235a012017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxytamoxifen 10V, Positive-QTOFsplash10-000i-1239000000-84645e53e8de455443fb2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxytamoxifen 20V, Positive-QTOFsplash10-00di-9455000000-9cfa2d15949946fc03c72016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxytamoxifen 40V, Positive-QTOFsplash10-00di-9261000000-b6bb4e0b0330b5c146c12016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxytamoxifen 10V, Negative-QTOFsplash10-000i-0009000000-ae47347b1ffe098e23742016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxytamoxifen 20V, Negative-QTOFsplash10-014r-1019000000-a006c4264d6b4b3d156f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxytamoxifen 40V, Negative-QTOFsplash10-014j-5296000000-6a3ed7fb5ff7614b731a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxytamoxifen 10V, Positive-QTOFsplash10-000i-0019000000-4e76d0dc813ddb3456862021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxytamoxifen 20V, Positive-QTOFsplash10-00dr-8139000000-e48c28363818f855eccb2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxytamoxifen 40V, Positive-QTOFsplash10-00di-9100000000-07129b6b7392d8ff3fdc2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxytamoxifen 10V, Negative-QTOFsplash10-000i-0009000000-d21bc4977cae5eb4e4dc2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxytamoxifen 20V, Negative-QTOFsplash10-000i-0009000000-608b9d736aade52153f22021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxytamoxifen 40V, Negative-QTOFsplash10-02tj-0089000000-2a7a41a55ad5dd8159012021-10-12Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
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
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available