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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-07-22 19:50:31 UTC
Update Date2019-07-23 07:15:50 UTC
HMDB IDHMDB0061140
Secondary Accession Numbers
  • HMDB61140
Metabolite Identification
Common NameEndoxifen sulfate
DescriptionEndoxifen 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. Endoxifen sulfate is a very strong basic compound (based on its pKa). endoxifen sulfate and adenosine 3',5'-diphosphate can be biosynthesized from endoxifen and phosphoadenosine phosphosulfate through the action of the enzyme sulfotransferase 1A1. Endoxifen sulfate is a metabolite of tamoxifen. In humans, endoxifen sulfate is involved in tamoxifen metabolism pathway. 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. Tamoxifen is an antagonist of the estrogen receptor in breast tissue via its active metabolite, hydroxytamoxifen.
Structure
Data?1563866150
Synonyms
ValueSource
Endoxifen sulfuric acidGenerator
Endoxifen sulphateGenerator
Endoxifen sulphuric acidGenerator
Chemical FormulaC25H27NO5S
Average Molecular Weight453.551
Monoisotopic Molecular Weight453.160993669
IUPAC Name{4-[(1E)-1-{4-[2-(methylamino)ethoxy]phenyl}-2-phenylbut-1-en-1-yl]phenyl}oxidanesulfonic acid
Traditional Name{4-[(1E)-1-{4-[2-(methylamino)ethoxy]phenyl}-2-phenylbut-1-en-1-yl]phenyl}oxidanesulfonic acid
CAS Registry NumberNot Available
SMILES
CC\C(=C(\C1=CC=C(OCCNC)C=C1)C1=CC=C(OS(O)(=O)=O)C=C1)C1=CC=CC=C1
InChI Identifier
InChI=1S/C25H27NO5S/c1-3-24(19-7-5-4-6-8-19)25(20-9-13-22(14-10-20)30-18-17-26-2)21-11-15-23(16-12-21)31-32(27,28)29/h4-16,26H,3,17-18H2,1-2H3,(H,27,28,29)/b25-24+
InChI KeyDHSITAIKYQFMGG-OCOZRVBESA-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
  • Secondary aliphatic amine
  • Ether
  • Secondary amine
  • Organonitrogen compound
  • Organic oxide
  • Amine
  • Organopnictogen compound
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
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 Solubility0.00052 g/LALOGPS
logP2.64ALOGPS
logP3.97ChemAxon
logS-5.9ALOGPS
pKa (Strongest Acidic)-2ChemAxon
pKa (Strongest Basic)9.51ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area84.86 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity135.11 m³·mol⁻¹ChemAxon
Polarizability49.07 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]+210.39731661259
DarkChem[M-H]-207.37331661259
DeepCCS[M+H]+209.76830932474
DeepCCS[M-H]-207.4130932474
DeepCCS[M-2H]-240.67830932474
DeepCCS[M+Na]+217.18230932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Endoxifen sulfateCC\C(=C(\C1=CC=C(OCCNC)C=C1)C1=CC=C(OS(O)(=O)=O)C=C1)C1=CC=CC=C15661.4Standard polar33892256
Endoxifen sulfateCC\C(=C(\C1=CC=C(OCCNC)C=C1)C1=CC=C(OS(O)(=O)=O)C=C1)C1=CC=CC=C13413.4Standard non polar33892256
Endoxifen sulfateCC\C(=C(\C1=CC=C(OCCNC)C=C1)C1=CC=C(OS(O)(=O)=O)C=C1)C1=CC=CC=C13579.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Endoxifen sulfate,1TMS,isomer #1CC/C(=C(/C1=CC=C(OCCNC)C=C1)C1=CC=C(OS(=O)(=O)O[Si](C)(C)C)C=C1)C1=CC=CC=C13780.4Semi standard non polar33892256
Endoxifen sulfate,1TMS,isomer #1CC/C(=C(/C1=CC=C(OCCNC)C=C1)C1=CC=C(OS(=O)(=O)O[Si](C)(C)C)C=C1)C1=CC=CC=C13604.8Standard non polar33892256
Endoxifen sulfate,1TMS,isomer #1CC/C(=C(/C1=CC=C(OCCNC)C=C1)C1=CC=C(OS(=O)(=O)O[Si](C)(C)C)C=C1)C1=CC=CC=C14913.4Standard polar33892256
Endoxifen sulfate,1TMS,isomer #2CC/C(=C(/C1=CC=C(OCCN(C)[Si](C)(C)C)C=C1)C1=CC=C(OS(=O)(=O)O)C=C1)C1=CC=CC=C14023.6Semi standard non polar33892256
Endoxifen sulfate,1TMS,isomer #2CC/C(=C(/C1=CC=C(OCCN(C)[Si](C)(C)C)C=C1)C1=CC=C(OS(=O)(=O)O)C=C1)C1=CC=CC=C13678.3Standard non polar33892256
Endoxifen sulfate,1TMS,isomer #2CC/C(=C(/C1=CC=C(OCCN(C)[Si](C)(C)C)C=C1)C1=CC=C(OS(=O)(=O)O)C=C1)C1=CC=CC=C15011.6Standard polar33892256
Endoxifen sulfate,2TMS,isomer #1CC/C(=C(/C1=CC=C(OCCN(C)[Si](C)(C)C)C=C1)C1=CC=C(OS(=O)(=O)O[Si](C)(C)C)C=C1)C1=CC=CC=C13910.1Semi standard non polar33892256
Endoxifen sulfate,2TMS,isomer #1CC/C(=C(/C1=CC=C(OCCN(C)[Si](C)(C)C)C=C1)C1=CC=C(OS(=O)(=O)O[Si](C)(C)C)C=C1)C1=CC=CC=C13761.8Standard non polar33892256
Endoxifen sulfate,2TMS,isomer #1CC/C(=C(/C1=CC=C(OCCN(C)[Si](C)(C)C)C=C1)C1=CC=C(OS(=O)(=O)O[Si](C)(C)C)C=C1)C1=CC=CC=C14709.6Standard polar33892256
Endoxifen sulfate,1TBDMS,isomer #1CC/C(=C(/C1=CC=C(OCCNC)C=C1)C1=CC=C(OS(=O)(=O)O[Si](C)(C)C(C)(C)C)C=C1)C1=CC=CC=C13991.6Semi standard non polar33892256
Endoxifen sulfate,1TBDMS,isomer #1CC/C(=C(/C1=CC=C(OCCNC)C=C1)C1=CC=C(OS(=O)(=O)O[Si](C)(C)C(C)(C)C)C=C1)C1=CC=CC=C13841.6Standard non polar33892256
Endoxifen sulfate,1TBDMS,isomer #1CC/C(=C(/C1=CC=C(OCCNC)C=C1)C1=CC=C(OS(=O)(=O)O[Si](C)(C)C(C)(C)C)C=C1)C1=CC=CC=C14833.1Standard polar33892256
Endoxifen sulfate,1TBDMS,isomer #2CC/C(=C(/C1=CC=C(OCCN(C)[Si](C)(C)C(C)(C)C)C=C1)C1=CC=C(OS(=O)(=O)O)C=C1)C1=CC=CC=C14240.5Semi standard non polar33892256
Endoxifen sulfate,1TBDMS,isomer #2CC/C(=C(/C1=CC=C(OCCN(C)[Si](C)(C)C(C)(C)C)C=C1)C1=CC=C(OS(=O)(=O)O)C=C1)C1=CC=CC=C13867.5Standard non polar33892256
Endoxifen sulfate,1TBDMS,isomer #2CC/C(=C(/C1=CC=C(OCCN(C)[Si](C)(C)C(C)(C)C)C=C1)C1=CC=C(OS(=O)(=O)O)C=C1)C1=CC=CC=C15015.9Standard polar33892256
Endoxifen sulfate,2TBDMS,isomer #1CC/C(=C(/C1=CC=C(OCCN(C)[Si](C)(C)C(C)(C)C)C=C1)C1=CC=C(OS(=O)(=O)O[Si](C)(C)C(C)(C)C)C=C1)C1=CC=CC=C14344.0Semi standard non polar33892256
Endoxifen sulfate,2TBDMS,isomer #1CC/C(=C(/C1=CC=C(OCCN(C)[Si](C)(C)C(C)(C)C)C=C1)C1=CC=C(OS(=O)(=O)O[Si](C)(C)C(C)(C)C)C=C1)C1=CC=CC=C14189.0Standard non polar33892256
Endoxifen sulfate,2TBDMS,isomer #1CC/C(=C(/C1=CC=C(OCCN(C)[Si](C)(C)C(C)(C)C)C=C1)C1=CC=C(OS(=O)(=O)O[Si](C)(C)C(C)(C)C)C=C1)C1=CC=CC=C14691.2Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Endoxifen sulfate GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9105200000-70048c179a2a85e6d5792017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Endoxifen 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 - Endoxifen sulfate 10V, Positive-QTOFsplash10-0udi-2204900000-c4e23e990b08fb5644622017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Endoxifen sulfate 20V, Positive-QTOFsplash10-0a4i-9326400000-d451d71578afcb6363f22017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Endoxifen sulfate 40V, Positive-QTOFsplash10-0a4l-9162000000-d391f022dd95428d9c732017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Endoxifen sulfate 10V, Negative-QTOFsplash10-0udi-0002900000-7e9696a907c4e1a035fc2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Endoxifen sulfate 20V, Negative-QTOFsplash10-00dj-1019100000-06fe6f3ab72d9e1d24f82017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Endoxifen sulfate 40V, Negative-QTOFsplash10-02aj-6039000000-046aafbff611957414e02017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Endoxifen sulfate 10V, Negative-QTOFsplash10-0udi-0001900000-5301293a20c59e1694a72021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Endoxifen sulfate 20V, Negative-QTOFsplash10-0udj-0009800000-810de3bf4102015ff5e12021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Endoxifen sulfate 40V, Negative-QTOFsplash10-0002-2019200000-221498ef3c2ba91dfd732021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Endoxifen sulfate 10V, Positive-QTOFsplash10-0udi-0001900000-9b7624d6450a69f0eb952021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Endoxifen sulfate 20V, Positive-QTOFsplash10-0zg0-1105900000-bc7792296e151943bbfb2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Endoxifen sulfate 40V, Positive-QTOFsplash10-05rr-9657100000-2dc572260c4e4c91fee82021-09-24Wishart 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 Compound131770047
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