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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-06-15 18:03:56 UTC
Update Date2019-07-23 07:14:42 UTC
HMDB IDHMDB0060615
Secondary Accession Numbers
  • HMDB60615
Metabolite Identification
Common NameNorendoxifen
DescriptionNorendoxifen is a metabolite of tamoxifen. Tamoxifen is an antagonist of the estrogen receptor in breast tissue via its active metabolite, hydroxytamoxifen. 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. (Wikipedia )
Structure
Data?1563866082
Synonyms
ValueSource
N,N-Didesmethyl-4-hydroxytamoxifenMeSH
Chemical FormulaC24H25NO2
Average Molecular Weight359.4608
Monoisotopic Molecular Weight359.188529049
IUPAC Name4-[(1Z)-1-[4-(2-aminoethoxy)phenyl]-2-phenylbut-1-en-1-yl]phenol
Traditional Name4-[(1Z)-1-[4-(2-aminoethoxy)phenyl]-2-phenylbut-1-en-1-yl]phenol
CAS Registry NumberNot Available
SMILES
CC\C(=C(/C1=CC=C(O)C=C1)C1=CC=C(OCCN)C=C1)C1=CC=CC=C1
InChI Identifier
InChI=1S/C24H25NO2/c1-2-23(18-6-4-3-5-7-18)24(19-8-12-21(26)13-9-19)20-10-14-22(15-11-20)27-17-16-25/h3-15,26H,2,16-17,25H2,1H3/b24-23-
InChI KeyYCQBLTPGQSYLHD-VHXPQNKSSA-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
  • Ether
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Amine
  • Primary amine
  • 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 Solubility0.0014 g/LALOGPS
logP5.11ALOGPS
logP4.65ChemAxon
logS-5.4ALOGPS
pKa (Strongest Acidic)9.62ChemAxon
pKa (Strongest Basic)9.01ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area55.48 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity120.34 m³·mol⁻¹ChemAxon
Polarizability41.26 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+185.10931661259
DarkChem[M-H]-188.94731661259
DeepCCS[M+H]+191.03430932474
DeepCCS[M-H]-188.67630932474
DeepCCS[M-2H]-222.91630932474
DeepCCS[M+Na]+198.14430932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
NorendoxifenCC\C(=C(/C1=CC=C(O)C=C1)C1=CC=C(OCCN)C=C1)C1=CC=CC=C14205.2Standard polar33892256
NorendoxifenCC\C(=C(/C1=CC=C(O)C=C1)C1=CC=C(OCCN)C=C1)C1=CC=CC=C12867.3Standard non polar33892256
NorendoxifenCC\C(=C(/C1=CC=C(O)C=C1)C1=CC=C(OCCN)C=C1)C1=CC=CC=C13062.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Norendoxifen,1TMS,isomer #1CC/C(=C(/C1=CC=C(OCCN)C=C1)C1=CC=C(O[Si](C)(C)C)C=C1)C1=CC=CC=C13358.2Semi standard non polar33892256
Norendoxifen,1TMS,isomer #2CC/C(=C(\C1=CC=C(O)C=C1)C1=CC=C(OCCN[Si](C)(C)C)C=C1)C1=CC=CC=C13470.7Semi standard non polar33892256
Norendoxifen,2TMS,isomer #1CC/C(=C(/C1=CC=C(OCCN[Si](C)(C)C)C=C1)C1=CC=C(O[Si](C)(C)C)C=C1)C1=CC=CC=C13378.8Semi standard non polar33892256
Norendoxifen,2TMS,isomer #1CC/C(=C(/C1=CC=C(OCCN[Si](C)(C)C)C=C1)C1=CC=C(O[Si](C)(C)C)C=C1)C1=CC=CC=C13143.7Standard non polar33892256
Norendoxifen,2TMS,isomer #1CC/C(=C(/C1=CC=C(OCCN[Si](C)(C)C)C=C1)C1=CC=C(O[Si](C)(C)C)C=C1)C1=CC=CC=C13768.1Standard polar33892256
Norendoxifen,2TMS,isomer #2CC/C(=C(\C1=CC=C(O)C=C1)C1=CC=C(OCCN([Si](C)(C)C)[Si](C)(C)C)C=C1)C1=CC=CC=C13587.9Semi standard non polar33892256
Norendoxifen,2TMS,isomer #2CC/C(=C(\C1=CC=C(O)C=C1)C1=CC=C(OCCN([Si](C)(C)C)[Si](C)(C)C)C=C1)C1=CC=CC=C13363.9Standard non polar33892256
Norendoxifen,2TMS,isomer #2CC/C(=C(\C1=CC=C(O)C=C1)C1=CC=C(OCCN([Si](C)(C)C)[Si](C)(C)C)C=C1)C1=CC=CC=C13922.5Standard polar33892256
Norendoxifen,3TMS,isomer #1CC/C(=C(/C1=CC=C(OCCN([Si](C)(C)C)[Si](C)(C)C)C=C1)C1=CC=C(O[Si](C)(C)C)C=C1)C1=CC=CC=C13577.2Semi standard non polar33892256
Norendoxifen,3TMS,isomer #1CC/C(=C(/C1=CC=C(OCCN([Si](C)(C)C)[Si](C)(C)C)C=C1)C1=CC=C(O[Si](C)(C)C)C=C1)C1=CC=CC=C13254.1Standard non polar33892256
Norendoxifen,3TMS,isomer #1CC/C(=C(/C1=CC=C(OCCN([Si](C)(C)C)[Si](C)(C)C)C=C1)C1=CC=C(O[Si](C)(C)C)C=C1)C1=CC=CC=C13659.1Standard polar33892256
Norendoxifen,1TBDMS,isomer #1CC/C(=C(/C1=CC=C(OCCN)C=C1)C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)C1=CC=CC=C13602.9Semi standard non polar33892256
Norendoxifen,1TBDMS,isomer #2CC/C(=C(\C1=CC=C(O)C=C1)C1=CC=C(OCCN[Si](C)(C)C(C)(C)C)C=C1)C1=CC=CC=C13685.0Semi standard non polar33892256
Norendoxifen,2TBDMS,isomer #1CC/C(=C(/C1=CC=C(OCCN[Si](C)(C)C(C)(C)C)C=C1)C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)C1=CC=CC=C13784.5Semi standard non polar33892256
Norendoxifen,2TBDMS,isomer #1CC/C(=C(/C1=CC=C(OCCN[Si](C)(C)C(C)(C)C)C=C1)C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)C1=CC=CC=C13524.2Standard non polar33892256
Norendoxifen,2TBDMS,isomer #1CC/C(=C(/C1=CC=C(OCCN[Si](C)(C)C(C)(C)C)C=C1)C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)C1=CC=CC=C13910.6Standard polar33892256
Norendoxifen,2TBDMS,isomer #2CC/C(=C(\C1=CC=C(O)C=C1)C1=CC=C(OCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1)C1=CC=CC=C14009.0Semi standard non polar33892256
Norendoxifen,2TBDMS,isomer #2CC/C(=C(\C1=CC=C(O)C=C1)C1=CC=C(OCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1)C1=CC=CC=C13634.3Standard non polar33892256
Norendoxifen,2TBDMS,isomer #2CC/C(=C(\C1=CC=C(O)C=C1)C1=CC=C(OCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1)C1=CC=CC=C13965.2Standard polar33892256
Norendoxifen,3TBDMS,isomer #1CC/C(=C(/C1=CC=C(OCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1)C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)C1=CC=CC=C14177.7Semi standard non polar33892256
Norendoxifen,3TBDMS,isomer #1CC/C(=C(/C1=CC=C(OCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1)C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)C1=CC=CC=C13743.3Standard non polar33892256
Norendoxifen,3TBDMS,isomer #1CC/C(=C(/C1=CC=C(OCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1)C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)C1=CC=CC=C13810.0Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Norendoxifen GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-7279000000-32107621c3f6595078f62017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Norendoxifen GC-MS (1 TMS) - 70eV, Positivesplash10-0089-7119500000-e3b9ef720e3dbf0be7332017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Norendoxifen 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 - Norendoxifen 10V, Positive-QTOFsplash10-03di-1239000000-88ce601bc7522cf285a92017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Norendoxifen 20V, Positive-QTOFsplash10-0006-9454000000-b3241e86f694240075fa2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Norendoxifen 40V, Positive-QTOFsplash10-0006-9251000000-960700e1a02ad6401dc12017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Norendoxifen 10V, Negative-QTOFsplash10-0a4i-0009000000-d67e1cb09cb9092cbe0e2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Norendoxifen 20V, Negative-QTOFsplash10-066r-0009000000-f7e8814bf3121dd23c4d2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Norendoxifen 40V, Negative-QTOFsplash10-014v-4295000000-e1acde4dc4d9e8f5810a2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Norendoxifen 10V, Positive-QTOFsplash10-03di-0019000000-551fa9b73e61e2fa24d82021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Norendoxifen 20V, Positive-QTOFsplash10-03xu-0149000000-44dbb0817f11c3a8cf1a2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Norendoxifen 40V, Positive-QTOFsplash10-014l-4933000000-c56c99a7aa326c60346d2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Norendoxifen 10V, Negative-QTOFsplash10-0aor-0009000000-82a8cbb419335df94a3d2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Norendoxifen 20V, Negative-QTOFsplash10-066r-0019000000-802c93db1df9e77c8ede2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Norendoxifen 40V, Negative-QTOFsplash10-00ks-0094000000-375dab9363ee50c7ead52021-10-12Wishart 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 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 LinkNorendoxifen
METLIN IDNot Available
PubChem Compound68037237
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