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Record Information
Version4.0
Creation Date2013-05-17 01:26:20 UTC
Update Date2017-09-23 14:19:16 UTC
HMDB IDHMDB0060513
Secondary Accession Numbers
  • HMDB60513
StatusExpected but not Quantified
Metabolite Identification
Common NameTamoxifen N-oxide
DescriptionTamoxifen N-oxide 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
Thumb
SynonymsNot Available
Chemical FormulaC26H29NO2
Average Molecular Weight387.514
Monoisotopic Molecular Weight387.219829177
IUPAC Name2-{4-[(1Z)-1,2-diphenylbut-1-en-1-yl]phenoxy}-N,N-dimethylethanamine oxide
Traditional Name2-{4-[(1Z)-1,2-diphenylbut-1-en-1-yl]phenoxy}-N,N-dimethylethanamine oxide
CAS Registry NumberNot Available
SMILES
CC\C(=C(/C1=CC=CC=C1)C1=CC=C(OCC[N+](C)(C)[O-])C=C1)C1=CC=CC=C1
InChI Identifier
InChI=1S/C26H29NO2/c1-4-25(21-11-7-5-8-12-21)26(22-13-9-6-10-14-22)23-15-17-24(18-16-23)29-20-19-27(2,3)28/h5-18H,4,19-20H2,1-3H3/b26-25-
InChI KeyYAASNACECBQAFW-QPLCGJKRSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities 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.
KingdomChemical entities
Super ClassOrganic compounds
ClassPhenylpropanoids and polyketides
Sub ClassStilbenes
Direct ParentStilbenes
Alternative Parents
Substituents
  • Stilbene
  • Diphenylmethane
  • Phenylpropane
  • Phenoxy compound
  • Phenol ether
  • Alkyl aryl ether
  • Monocyclic benzene moiety
  • Benzenoid
  • Trialkyl amine oxide
  • N-oxide
  • Ether
  • Trisubstituted n-oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Process
Naturally occurring process:
Biological process:
Biochemical pathway:
Disposition
Biological Location:
Source:
Subcellular:
Biofluid and excreta:
Organ and components:
Role
Biological role:
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.000202 mg/mLALOGPS
logP3.65ALOGPS
logP5.23ChemAxon
logS-6.3ALOGPS
pKa (Strongest Basic)3.27ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area36.11 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity130.48 m3·mol-1ChemAxon
Polarizability44.89 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
Pathways
NameSMPDB/PathwhizKEGG
Tamoxifen Metabolism PathwayPw000582Pw000582 greyscalePw000582 simpleNot Available
Tamoxifen PathwayPw000250Pw000250 greyscalePw000250 simpleNot Available
Displaying all 2 entries
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableNormal
    details
    UrineExpected but not Quantified Not AvailableNot AvailableNormal
      details
      Abnormal Concentrations
      Not Available
      Associated Disorders and Diseases
      Disease ReferencesNone
      Associated OMIM IDsNone
      DrugBank IDNot Available
      DrugBank Metabolite IDDBMET00032
      Phenol Explorer Compound IDNot Available
      Phenol Explorer Metabolite IDNot Available
      FoodDB IDNot Available
      KNApSAcK IDNot Available
      Chemspider IDNot Available
      KEGG Compound IDC16545
      BioCyc IDNot Available
      BiGG IDNot Available
      Wikipedia LinkNot Available
      NuGOwiki LinkHMDB0060513
      METLIN IDNot Available
      PubChem Compound0
      PDB IDNot Available
      ChEBI ID63825
      References
      Synthesis ReferenceNot Available
      Material Safety Data Sheet (MSDS)Not Available
      General References
      1. Magrane M: UniProt Knowledgebase: a hub of integrated protein data. Database (Oxford). 2011 Mar 29;2011:bar009. doi: 10.1093/database/bar009. Print 2011. [PubMed:21447597 ]

      Enzymes

      General function:
      Involved in flavin-containing monooxygenase activity
      Specific function:
      In contrast with other forms of FMO it does not seem to be a drug-metabolizing enzyme.
      Gene Name:
      FMO5
      Uniprot ID:
      P49326
      Molecular weight:
      32480.04
      Reactions
      Tamoxifen + Oxygen + NADPH + Hydrogen Ion → Tamoxifen N-oxide + NADP + Waterdetails
      General function:
      Involved in flavin-containing monooxygenase activity
      Specific function:
      Catalyzes the N-oxidation of certain primary alkylamines to their oximes via an N-hydroxylamine intermediate. Inactive toward certain tertiary amines, such as imipramine or chloropromazine. Can catalyze the S-oxidation of methimazole. The truncated form is catalytically inactive.
      Gene Name:
      FMO2
      Uniprot ID:
      Q99518
      Molecular weight:
      53643.29
      Reactions
      Tamoxifen + Oxygen + NADPH + Hydrogen Ion → Tamoxifen N-oxide + NADP + Waterdetails
      General function:
      Involved in flavin-containing monooxygenase activity
      Specific function:
      This protein is involved in the oxidative metabolism of a variety of xenobiotics such as drugs and pesticides.
      Gene Name:
      FMO4
      Uniprot ID:
      P31512
      Molecular weight:
      63342.055
      Reactions
      Tamoxifen + Oxygen + NADPH + Hydrogen Ion → Tamoxifen N-oxide + NADP + Waterdetails
      General function:
      Involved in flavin-containing monooxygenase activity
      Specific function:
      Involved in the oxidative metabolism of a variety of xenobiotics such as drugs and pesticides. It N-oxygenates primary aliphatic alkylamines as well as secondary and tertiary amines. Plays an important role in the metabolism of trimethylamine (TMA), via the production of TMA N-oxide (TMAO). Is also able to perform S-oxidation when acting on sulfide compounds.
      Gene Name:
      FMO3
      Uniprot ID:
      P31513
      Molecular weight:
      60032.975
      Reactions
      Tamoxifen + Oxygen + NADPH + Hydrogen Ion → Tamoxifen N-oxide + NADP + Waterdetails
      General function:
      Involved in flavin-containing monooxygenase activity
      Specific function:
      This protein is involved in the oxidative metabolism of a variety of xenobiotics such as drugs and pesticides. Form I catalyzes the N-oxygenation of secondary and tertiary amines.
      Gene Name:
      FMO1
      Uniprot ID:
      Q01740
      Molecular weight:
      60310.285
      Reactions
      Tamoxifen + Oxygen + NADPH + Hydrogen Ion → Tamoxifen N-oxide + NADP + Waterdetails