Hmdb loader
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-06-15 17:09:48 UTC
Update Date2021-09-14 15:02:27 UTC
HMDB IDHMDB0060585
Secondary Accession Numbers
  • HMDB60585
Metabolite Identification
Common Namealpha-Hydroxytamoxifen
Descriptionalpha-Hydroxytamoxifen 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?1563866079
Synonyms
ValueSource
a-HydroxytamoxifenGenerator
Α-hydroxytamoxifenGenerator
trans-Hydroxy-tamoxifenHMDB
Chemical FormulaC26H29NO2
Average Molecular Weight387.514
Monoisotopic Molecular Weight387.219829177
IUPAC Name(3E)-4-{4-[2-(dimethylamino)ethoxy]phenyl}-3,4-diphenylbut-3-en-2-ol
Traditional Nameα-hydroxytamoxifen
CAS Registry NumberNot Available
SMILES
CC(O)C(=C(/C1=CC=CC=C1)C1=CC=C(OCCN(C)C)C=C1)\C1=CC=CC=C1
InChI Identifier
InChI=1S/C26H29NO2/c1-20(28)25(21-10-6-4-7-11-21)26(22-12-8-5-9-13-22)23-14-16-24(17-15-23)29-19-18-27(2)3/h4-17,20,28H,18-19H2,1-3H3/b26-25-
InChI KeyBPHFBQJMFWCHGH-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
  • Cinnamyl alcohol
  • Phenylpropane
  • Phenoxy compound
  • Phenol ether
  • Alkyl aryl ether
  • Benzenoid
  • Monocyclic benzene moiety
  • Tertiary aliphatic amine
  • Tertiary amine
  • Secondary alcohol
  • Ether
  • Organopnictogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Alcohol
  • Organic nitrogen compound
  • Organic oxygen compound
  • Amine
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
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 Solubility0.005 g/LALOGPS
logP4.59ALOGPS
logP5.04ChemAxon
logS-4.9ALOGPS
pKa (Strongest Acidic)14.8ChemAxon
pKa (Strongest Basic)8.76ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area32.7 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity130.02 m³·mol⁻¹ChemAxon
Polarizability44.92 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
DarkChem[M+H]+193.51531661259
DarkChem[M-H]-190.92331661259
DeepCCS[M+H]+196.92230932474
DeepCCS[M-H]-194.56430932474
DeepCCS[M-2H]-228.53430932474
DeepCCS[M+Na]+203.74830932474
AllCCS[M+H]+199.032859911
AllCCS[M+H-H2O]+196.232859911
AllCCS[M+NH4]+201.632859911
AllCCS[M+Na]+202.332859911
AllCCS[M-H]-201.432859911
AllCCS[M+Na-2H]-201.532859911
AllCCS[M+HCOO]-201.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
alpha-HydroxytamoxifenCC(O)C(=C(/C1=CC=CC=C1)C1=CC=C(OCCN(C)C)C=C1)\C1=CC=CC=C13864.4Standard polar33892256
alpha-HydroxytamoxifenCC(O)C(=C(/C1=CC=CC=C1)C1=CC=C(OCCN(C)C)C=C1)\C1=CC=CC=C12877.4Standard non polar33892256
alpha-HydroxytamoxifenCC(O)C(=C(/C1=CC=CC=C1)C1=CC=C(OCCN(C)C)C=C1)\C1=CC=CC=C12892.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
alpha-Hydroxytamoxifen,1TMS,isomer #1CC(O[Si](C)(C)C)/C(=C(\C1=CC=CC=C1)C1=CC=C(OCCN(C)C)C=C1)C1=CC=CC=C13078.7Semi standard non polar33892256
alpha-Hydroxytamoxifen,1TBDMS,isomer #1CC(O[Si](C)(C)C(C)(C)C)/C(=C(\C1=CC=CC=C1)C1=CC=C(OCCN(C)C)C=C1)C1=CC=CC=C13292.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - alpha-Hydroxytamoxifen GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4l-7029000000-c8420989ed0d4369bee72017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - alpha-Hydroxytamoxifen GC-MS (1 TMS) - 70eV, Positivesplash10-0ab9-9013200000-83c686d077c522ee7b252017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - alpha-Hydroxytamoxifen 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-Hydroxytamoxifen 10V, Positive-QTOFsplash10-0fki-1039000000-a078ff95fdbf737284ca2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Hydroxytamoxifen 20V, Positive-QTOFsplash10-00di-9256000000-1bb80c696efd7ce8d1222017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Hydroxytamoxifen 40V, Positive-QTOFsplash10-05gj-9282000000-f899d24213bea6da8cb72017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Hydroxytamoxifen 10V, Negative-QTOFsplash10-000i-0009000000-db16a38f512cbe2734f82017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Hydroxytamoxifen 20V, Negative-QTOFsplash10-014s-1039000000-df3784bba7afad6483d52017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Hydroxytamoxifen 40V, Negative-QTOFsplash10-01ca-3294000000-06d595ee3c90e98612f32017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Hydroxytamoxifen 10V, Positive-QTOFsplash10-000i-0009000000-1ddeceae57910eb06d822021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Hydroxytamoxifen 20V, Positive-QTOFsplash10-00dr-7629000000-91e9f5e5064ccf6ac7c72021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Hydroxytamoxifen 40V, Positive-QTOFsplash10-00di-9010000000-80a1cd42f0b9eaa07cde2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Hydroxytamoxifen 10V, Negative-QTOFsplash10-000i-0009000000-107ce40cc8b6e774bc6a2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Hydroxytamoxifen 20V, Negative-QTOFsplash10-00kp-0039000000-ab70230bcaa8839e33b72021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Hydroxytamoxifen 40V, Negative-QTOFsplash10-0002-0092000000-9a61bde8be398d5a65b62021-10-12Wishart 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 IDC16544
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound3036580
PDB IDNot Available
ChEBI ID80553
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