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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-07-22 19:49:15 UTC
Update Date2019-07-23 07:15:48 UTC
HMDB IDHMDB0061123
Secondary Accession Numbers
  • HMDB61123
Metabolite Identification
Common Name4-Hydroxytamoxifen sulfate
Description4-Hydroxytamoxifen sulfate 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 sulfate is a very strong basic compound (based on its pKa). 4-hydroxytamoxifen sulfate and adenosine 3',5'-diphosphate can be biosynthesized from 4-hydroxytamoxifen and phosphoadenosine phosphosulfate; which is catalyzed by the enzyme sulfotransferase 1A1. In humans, 4-hydroxytamoxifen sulfate is involved in tamoxifen metabolism pathway. 4-Hydroxytamoxifen sulfate is a metabolite of tamoxifen. In other tissues such as the endometrium, it behaves as an agonist, and thus may be characterized as a mixed agonist/antagonist. Tamoxifen is an antagonist of the estrogen receptor in breast tissue via its active metabolite, hydroxytamoxifen. 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.
Structure
Data?1563866148
Synonyms
ValueSource
4-Hydroxytamoxifen sulfuric acidGenerator
4-Hydroxytamoxifen sulphateGenerator
4-Hydroxytamoxifen sulphuric acidGenerator
Chemical FormulaC26H29NO5S
Average Molecular Weight467.577
Monoisotopic Molecular Weight467.176643733
IUPAC Name{4-[(1Z)-1-{4-[2-(dimethylamino)ethoxy]phenyl}-2-phenylbut-1-en-1-yl]phenyl}oxidanesulfonic acid
Traditional Name{4-[(1Z)-1-{4-[2-(dimethylamino)ethoxy]phenyl}-2-phenylbut-1-en-1-yl]phenyl}oxidanesulfonic acid
CAS Registry NumberNot Available
SMILES
CC\C(=C(/C1=CC=C(OCCN(C)C)C=C1)C1=CC=C(OS(O)(=O)=O)C=C1)C1=CC=CC=C1
InChI Identifier
InChI=1S/C26H29NO5S/c1-4-25(20-8-6-5-7-9-20)26(22-12-16-24(17-13-22)32-33(28,29)30)21-10-14-23(15-11-21)31-19-18-27(2)3/h5-17H,4,18-19H2,1-3H3,(H,28,29,30)/b26-25-
InChI KeyCFSXIBDXCWVFJR-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
  • Phenylsulfate
  • Arylsulfate
  • Phenylpropane
  • Phenoxy compound
  • Phenol ether
  • Alkyl aryl ether
  • Monocyclic benzene moiety
  • Benzenoid
  • Sulfuric acid ester
  • Sulfate-ester
  • Sulfuric acid monoester
  • Organic sulfuric acid or derivatives
  • Tertiary aliphatic amine
  • Tertiary amine
  • Ether
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Process
RoleNot Available
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 Solubility0.00066 g/LALOGPS
logP3.16ALOGPS
logP4.09ChemAxon
logS-5.8ALOGPS
pKa (Strongest Acidic)-2ChemAxon
pKa (Strongest Basic)8.76ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area76.07 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity140.4 m³·mol⁻¹ChemAxon
Polarizability50.99 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+209.30231661259
DarkChem[M-H]-204.0131661259
DeepCCS[M+H]+211.79230932474
DeepCCS[M-H]-209.43430932474
DeepCCS[M-2H]-242.3230932474
DeepCCS[M+Na]+218.79230932474
AllCCS[M+H]+214.732859911
AllCCS[M+H-H2O]+212.432859911
AllCCS[M+NH4]+216.832859911
AllCCS[M+Na]+217.432859911
AllCCS[M-H]-209.432859911
AllCCS[M+Na-2H]-210.032859911
AllCCS[M+HCOO]-210.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
4-Hydroxytamoxifen sulfateCC\C(=C(/C1=CC=C(OCCN(C)C)C=C1)C1=CC=C(OS(O)(=O)=O)C=C1)C1=CC=CC=C15816.6Standard polar33892256
4-Hydroxytamoxifen sulfateCC\C(=C(/C1=CC=C(OCCN(C)C)C=C1)C1=CC=C(OS(O)(=O)=O)C=C1)C1=CC=CC=C13364.7Standard non polar33892256
4-Hydroxytamoxifen sulfateCC\C(=C(/C1=CC=C(OCCN(C)C)C=C1)C1=CC=C(OS(O)(=O)=O)C=C1)C1=CC=CC=C13547.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
4-Hydroxytamoxifen sulfate,1TMS,isomer #1CC/C(=C(\C1=CC=C(OCCN(C)C)C=C1)C1=CC=C(OS(=O)(=O)O[Si](C)(C)C)C=C1)C1=CC=CC=C13794.3Semi standard non polar33892256
4-Hydroxytamoxifen sulfate,1TMS,isomer #1CC/C(=C(\C1=CC=C(OCCN(C)C)C=C1)C1=CC=C(OS(=O)(=O)O[Si](C)(C)C)C=C1)C1=CC=CC=C13576.0Standard non polar33892256
4-Hydroxytamoxifen sulfate,1TMS,isomer #1CC/C(=C(\C1=CC=C(OCCN(C)C)C=C1)C1=CC=C(OS(=O)(=O)O[Si](C)(C)C)C=C1)C1=CC=CC=C14824.0Standard polar33892256
4-Hydroxytamoxifen sulfate,1TBDMS,isomer #1CC/C(=C(\C1=CC=C(OCCN(C)C)C=C1)C1=CC=C(OS(=O)(=O)O[Si](C)(C)C(C)(C)C)C=C1)C1=CC=CC=C13990.2Semi standard non polar33892256
4-Hydroxytamoxifen sulfate,1TBDMS,isomer #1CC/C(=C(\C1=CC=C(OCCN(C)C)C=C1)C1=CC=C(OS(=O)(=O)O[Si](C)(C)C(C)(C)C)C=C1)C1=CC=CC=C13804.1Standard non polar33892256
4-Hydroxytamoxifen sulfate,1TBDMS,isomer #1CC/C(=C(\C1=CC=C(OCCN(C)C)C=C1)C1=CC=C(OS(=O)(=O)O[Si](C)(C)C(C)(C)C)C=C1)C1=CC=CC=C14742.0Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 4-Hydroxytamoxifen sulfate GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9105300000-281ce7bb2bcc359bf42a2017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Hydroxytamoxifen sulfate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxytamoxifen sulfate 10V, Positive-QTOFsplash10-014i-2204900000-327101608ec2ca7a56cd2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxytamoxifen sulfate 20V, Positive-QTOFsplash10-00di-9216300000-4af687258d4cfde9e93c2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxytamoxifen sulfate 40V, Positive-QTOFsplash10-00di-9161000000-03d445444a0ab8bb24512017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxytamoxifen sulfate 10V, Negative-QTOFsplash10-014i-0002900000-88b47be6f2ce73bc67212017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxytamoxifen sulfate 20V, Negative-QTOFsplash10-00kk-1019100000-78a286ee089c12591a112017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxytamoxifen sulfate 40V, Negative-QTOFsplash10-02aj-6029000000-b3cfa964abf4e35690732017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxytamoxifen sulfate 10V, Negative-QTOFsplash10-014i-0000900000-378ee7c1537c13d5d54f2021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxytamoxifen sulfate 20V, Negative-QTOFsplash10-014i-0003900000-acbd4507f1c7310bbabf2021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxytamoxifen sulfate 40V, Negative-QTOFsplash10-0002-1009100000-6d6c40b2d651da8e34632021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxytamoxifen sulfate 10V, Positive-QTOFsplash10-014i-0001900000-7d49441c07e11b52fbea2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxytamoxifen sulfate 20V, Positive-QTOFsplash10-0g4i-7104900000-2f6167294f4c314cafe82021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxytamoxifen sulfate 40V, Positive-QTOFsplash10-00di-9000000000-872d794c8ec6ebd783d42021-09-25Wishart 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 IDNot Available
Phenol Explorer Compound IDNot Available
FooDB 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 Compound131770034
PDB IDNot Available
ChEBI IDNot Available
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