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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-07-09 16:15:15 UTC
Update Date2019-07-23 07:15:40 UTC
HMDB IDHMDB0061051
Secondary Accession Numbers
  • HMDB61051
Metabolite Identification
Common NameN-desmethyltoremifene
DescriptionN-desmethyltoremifene 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. N-desmethyltoremifene is a metabolite of toremifene. N-desmethyltoremifene is a very strong basic compound (based on its pKa). Toremifene citrate is an oral selective estrogen receptor modulator (SERM) which helps oppose the actions of estrogen in the body. Licensed in the United States under the brand name Fareston, toremifene citrate is FDA-approved for use in advanced breast cancer. It is also being evaluated for prevention of prostate cancer under the brand name Acapodene.
Structure
Data?1563866140
Synonyms
ValueSource
N-DemethyltoremifeneHMDB
N-Desmethyltoremifene, (e)-isomerHMDB
Chemical FormulaC25H26ClNO
Average Molecular Weight391.933
Monoisotopic Molecular Weight391.170292166
IUPAC Name(2-{4-[(1Z)-4-chloro-1,2-diphenylbut-1-en-1-yl]phenoxy}ethyl)(methyl)amine
Traditional Name(2-{4-[(1Z)-4-chloro-1,2-diphenylbut-1-en-1-yl]phenoxy}ethyl)(methyl)amine
CAS Registry NumberNot Available
SMILES
CNCCOC1=CC=C(C=C1)C(=C(\CCCl)C1=CC=CC=C1)\C1=CC=CC=C1
InChI Identifier
InChI=1S/C25H26ClNO/c1-27-18-19-28-23-14-12-22(13-15-23)25(21-10-6-3-7-11-21)24(16-17-26)20-8-4-2-5-9-20/h2-15,27H,16-19H2,1H3/b25-24-
InChI KeyWKJKBQYEFAFHCY-IZHYLOQSSA-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
  • Phenoxy compound
  • Phenol ether
  • Alkyl aryl ether
  • Monocyclic benzene moiety
  • Benzenoid
  • Secondary amine
  • Ether
  • Secondary aliphatic amine
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Amine
  • Alkyl halide
  • Hydrocarbon derivative
  • Alkyl chloride
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
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 Solubility0.00017 g/LALOGPS
logP5.76ALOGPS
logP5.89ChemAxon
logS-6.4ALOGPS
pKa (Strongest Basic)9.51ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area21.26 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity128.12 m³·mol⁻¹ChemAxon
Polarizability44.62 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
DeepCCS[M+H]+196.84830932474
DeepCCS[M-H]-194.26130932474
DeepCCS[M-2H]-228.78230932474
DeepCCS[M+Na]+204.49630932474
AllCCS[M+H]+196.832859911
AllCCS[M+H-H2O]+194.032859911
AllCCS[M+NH4]+199.332859911
AllCCS[M+Na]+200.032859911
AllCCS[M-H]-193.732859911
AllCCS[M+Na-2H]-193.232859911
AllCCS[M+HCOO]-192.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
N-desmethyltoremifeneCNCCOC1=CC=C(C=C1)C(=C(\CCCl)C1=CC=CC=C1)\C1=CC=CC=C14141.4Standard polar33892256
N-desmethyltoremifeneCNCCOC1=CC=C(C=C1)C(=C(\CCCl)C1=CC=CC=C1)\C1=CC=CC=C13062.4Standard non polar33892256
N-desmethyltoremifeneCNCCOC1=CC=C(C=C1)C(=C(\CCCl)C1=CC=CC=C1)\C1=CC=CC=C13014.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
N-desmethyltoremifene,1TMS,isomer #1CN(CCOC1=CC=C(/C(=C(/CCCl)C2=CC=CC=C2)C2=CC=CC=C2)C=C1)[Si](C)(C)C3412.7Semi standard non polar33892256
N-desmethyltoremifene,1TMS,isomer #1CN(CCOC1=CC=C(/C(=C(/CCCl)C2=CC=CC=C2)C2=CC=CC=C2)C=C1)[Si](C)(C)C3216.4Standard non polar33892256
N-desmethyltoremifene,1TMS,isomer #1CN(CCOC1=CC=C(/C(=C(/CCCl)C2=CC=CC=C2)C2=CC=CC=C2)C=C1)[Si](C)(C)C4015.2Standard polar33892256
N-desmethyltoremifene,1TBDMS,isomer #1CN(CCOC1=CC=C(/C(=C(/CCCl)C2=CC=CC=C2)C2=CC=CC=C2)C=C1)[Si](C)(C)C(C)(C)C3624.3Semi standard non polar33892256
N-desmethyltoremifene,1TBDMS,isomer #1CN(CCOC1=CC=C(/C(=C(/CCCl)C2=CC=CC=C2)C2=CC=CC=C2)C=C1)[Si](C)(C)C(C)(C)C3396.4Standard non polar33892256
N-desmethyltoremifene,1TBDMS,isomer #1CN(CCOC1=CC=C(/C(=C(/CCCl)C2=CC=CC=C2)C2=CC=CC=C2)C=C1)[Si](C)(C)C(C)(C)C4055.6Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - N-desmethyltoremifene GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9033000000-3948160a9f73f997e92a2017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-desmethyltoremifene 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 - N-desmethyltoremifene 10V, Positive-QTOFsplash10-0006-1119000000-7fe104edfdaaacaf8b962017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-desmethyltoremifene 20V, Positive-QTOFsplash10-0a4i-9237000000-c914a2d48019610106d42017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-desmethyltoremifene 40V, Positive-QTOFsplash10-0a4l-7091000000-c50fa529f1f94d67648e2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-desmethyltoremifene 10V, Negative-QTOFsplash10-0006-1009000000-68ba93a0d04446c5d4c12017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-desmethyltoremifene 20V, Negative-QTOFsplash10-001l-1029000000-f0d5f189dbdcb8eb75252017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-desmethyltoremifene 40V, Negative-QTOFsplash10-001i-6189000000-b4470fdb0dda4e06d65b2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-desmethyltoremifene 10V, Negative-QTOFsplash10-0006-1009000000-c63f847dc3e5831b77e32021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-desmethyltoremifene 20V, Negative-QTOFsplash10-001l-9038000000-013adbca58f3599996302021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-desmethyltoremifene 40V, Negative-QTOFsplash10-0002-0094000000-6e0338f47c66abc25cef2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-desmethyltoremifene 10V, Positive-QTOFsplash10-0006-0009000000-f75a20bf7b62259d06fc2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-desmethyltoremifene 20V, Positive-QTOFsplash10-0006-0049000000-210bbd22f64b6df7e4e82021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-desmethyltoremifene 40V, Positive-QTOFsplash10-015c-1951000000-14f8d51171c4453b945d2021-09-24Wishart 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 Compound3035212
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