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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-06-18 18:42:05 UTC
Update Date2021-09-14 14:58:53 UTC
HMDB IDHMDB0060668
Secondary Accession Numbers
  • HMDB60668
Metabolite Identification
Common Namealpha-Hydroxy-N-desmethyltamoxifen
Descriptionalpha-Hydroxy-N-desmethyltamoxifen 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?1563866089
Synonyms
ValueSource
a-Hydroxy-N-desmethyltamoxifenGenerator
Α-hydroxy-N-desmethyltamoxifenGenerator
Chemical FormulaC25H27NO2
Average Molecular Weight373.4874
Monoisotopic Molecular Weight373.204179113
IUPAC Name(3E)-4-{4-[2-(methylamino)ethoxy]phenyl}-3,4-diphenylbut-3-en-2-ol
Traditional Nameα-hydroxy-N-desmethyltamoxifen
CAS Registry NumberNot Available
SMILES
CNCCOC1=CC=C(C=C1)C(=C(\C(C)O)C1=CC=CC=C1)\C1=CC=CC=C1
InChI Identifier
InChI=1S/C25H27NO2/c1-19(27)24(20-9-5-3-6-10-20)25(21-11-7-4-8-12-21)22-13-15-23(16-14-22)28-18-17-26-2/h3-16,19,26-27H,17-18H2,1-2H3/b25-24-
InChI KeyGREXPZNIZPCGIV-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
  • Cinnamyl alcohol
  • Phenylpropane
  • Phenoxy compound
  • Phenol ether
  • Alkyl aryl ether
  • Monocyclic benzene moiety
  • Benzenoid
  • Secondary alcohol
  • Secondary amine
  • Ether
  • Secondary aliphatic amine
  • Organopnictogen compound
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Alcohol
  • Organic nitrogen compound
  • Amine
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
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 Solubility0.0014 g/LALOGPS
logP4.82ALOGPS
logP4.66ChemAxon
logS-5.4ALOGPS
pKa (Strongest Acidic)14.8ChemAxon
pKa (Strongest Basic)9.51ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area41.49 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity124.73 m³·mol⁻¹ChemAxon
Polarizability43.23 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]+190.92631661259
DarkChem[M-H]-188.81831661259
DeepCCS[M+H]+196.57230932474
DeepCCS[M-H]-194.21430932474
DeepCCS[M-2H]-228.48530932474
DeepCCS[M+Na]+203.78130932474
AllCCS[M+H]+195.632859911
AllCCS[M+H-H2O]+192.632859911
AllCCS[M+NH4]+198.332859911
AllCCS[M+Na]+199.032859911
AllCCS[M-H]-197.032859911
AllCCS[M+Na-2H]-197.032859911
AllCCS[M+HCOO]-197.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
alpha-Hydroxy-N-desmethyltamoxifenCNCCOC1=CC=C(C=C1)C(=C(\C(C)O)C1=CC=CC=C1)\C1=CC=CC=C13790.2Standard polar33892256
alpha-Hydroxy-N-desmethyltamoxifenCNCCOC1=CC=C(C=C1)C(=C(\C(C)O)C1=CC=CC=C1)\C1=CC=CC=C12880.9Standard non polar33892256
alpha-Hydroxy-N-desmethyltamoxifenCNCCOC1=CC=C(C=C1)C(=C(\C(C)O)C1=CC=CC=C1)\C1=CC=CC=C12930.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
alpha-Hydroxy-N-desmethyltamoxifen,1TMS,isomer #1CNCCOC1=CC=C(/C(=C(\C2=CC=CC=C2)C(C)O[Si](C)(C)C)C2=CC=CC=C2)C=C13061.8Semi standard non polar33892256
alpha-Hydroxy-N-desmethyltamoxifen,1TMS,isomer #2CC(O)/C(=C(\C1=CC=CC=C1)C1=CC=C(OCCN(C)[Si](C)(C)C)C=C1)C1=CC=CC=C13239.3Semi standard non polar33892256
alpha-Hydroxy-N-desmethyltamoxifen,2TMS,isomer #1CC(O[Si](C)(C)C)/C(=C(\C1=CC=CC=C1)C1=CC=C(OCCN(C)[Si](C)(C)C)C=C1)C1=CC=CC=C13202.9Semi standard non polar33892256
alpha-Hydroxy-N-desmethyltamoxifen,2TMS,isomer #1CC(O[Si](C)(C)C)/C(=C(\C1=CC=CC=C1)C1=CC=C(OCCN(C)[Si](C)(C)C)C=C1)C1=CC=CC=C12976.2Standard non polar33892256
alpha-Hydroxy-N-desmethyltamoxifen,2TMS,isomer #1CC(O[Si](C)(C)C)/C(=C(\C1=CC=CC=C1)C1=CC=C(OCCN(C)[Si](C)(C)C)C=C1)C1=CC=CC=C13678.6Standard polar33892256
alpha-Hydroxy-N-desmethyltamoxifen,1TBDMS,isomer #1CNCCOC1=CC=C(/C(=C(\C2=CC=CC=C2)C(C)O[Si](C)(C)C(C)(C)C)C2=CC=CC=C2)C=C13294.8Semi standard non polar33892256
alpha-Hydroxy-N-desmethyltamoxifen,1TBDMS,isomer #2CC(O)/C(=C(\C1=CC=CC=C1)C1=CC=C(OCCN(C)[Si](C)(C)C(C)(C)C)C=C1)C1=CC=CC=C13471.1Semi standard non polar33892256
alpha-Hydroxy-N-desmethyltamoxifen,2TBDMS,isomer #1CC(O[Si](C)(C)C(C)(C)C)/C(=C(\C1=CC=CC=C1)C1=CC=C(OCCN(C)[Si](C)(C)C(C)(C)C)C=C1)C1=CC=CC=C13622.7Semi standard non polar33892256
alpha-Hydroxy-N-desmethyltamoxifen,2TBDMS,isomer #1CC(O[Si](C)(C)C(C)(C)C)/C(=C(\C1=CC=CC=C1)C1=CC=C(OCCN(C)[Si](C)(C)C(C)(C)C)C=C1)C1=CC=CC=C13374.8Standard non polar33892256
alpha-Hydroxy-N-desmethyltamoxifen,2TBDMS,isomer #1CC(O[Si](C)(C)C(C)(C)C)/C(=C(\C1=CC=CC=C1)C1=CC=C(OCCN(C)[Si](C)(C)C(C)(C)C)C=C1)C1=CC=CC=C13813.8Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - alpha-Hydroxy-N-desmethyltamoxifen GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9054000000-e15dec26d63e4d9bb7492017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - alpha-Hydroxy-N-desmethyltamoxifen GC-MS (1 TMS) - 70eV, Positivesplash10-0006-9003000000-a784c69aff4a496763f32017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - alpha-Hydroxy-N-desmethyltamoxifen GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - alpha-Hydroxy-N-desmethyltamoxifen 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 - alpha-Hydroxy-N-desmethyltamoxifen 10V, Positive-QTOFsplash10-0ab9-1049000000-fa179e1fc4cb9d8b5b052017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Hydroxy-N-desmethyltamoxifen 20V, Positive-QTOFsplash10-0a4i-9276000000-6ba9741bb3c7ad9604092017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Hydroxy-N-desmethyltamoxifen 40V, Positive-QTOFsplash10-0537-9182000000-345aee5668b27c53461f2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Hydroxy-N-desmethyltamoxifen 10V, Negative-QTOFsplash10-00di-0009000000-8d280950bd0bc575fe272017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Hydroxy-N-desmethyltamoxifen 20V, Negative-QTOFsplash10-00xs-1049000000-6a22be13943fc2015cf02017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Hydroxy-N-desmethyltamoxifen 40V, Negative-QTOFsplash10-06ej-4293000000-f8a5b26e68804f3e0bd72017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Hydroxy-N-desmethyltamoxifen 10V, Positive-QTOFsplash10-00di-0009000000-9fa0eee7a3a875dd00352021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Hydroxy-N-desmethyltamoxifen 20V, Positive-QTOFsplash10-01bi-1779000000-f1bb7d3d2ec9b3fa92152021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Hydroxy-N-desmethyltamoxifen 40V, Positive-QTOFsplash10-05nb-3975000000-43c4a63a2ddf9f229c5e2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Hydroxy-N-desmethyltamoxifen 10V, Negative-QTOFsplash10-00di-0009000000-c60bf8d5da2347888ba92021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Hydroxy-N-desmethyltamoxifen 20V, Negative-QTOFsplash10-004j-0079000000-35d678ea07ba1348f1512021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Hydroxy-N-desmethyltamoxifen 40V, Negative-QTOFsplash10-0002-0092000000-af27fa768ce6ce5a4b482021-10-12Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • 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 IDC16549
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10474509
PDB IDNot Available
ChEBI ID80557
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