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Record Information
Version3.6
Creation Date2013-06-15 18:04:00 UTC
Update Date2016-02-11 08:09:24 UTC
HMDB IDHMDB60616
Secondary Accession NumbersNone
Metabolite Identification
Common NameTamoxifen-N-glucuronide
DescriptionTamoxifen-N-glucuronide 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
Synonyms
ValueSource
Tamoxifen N-glucuronideChEBI
Chemical FormulaC32H38NO7
Average Molecular Weight548.6466
Monoisotopic Molecular Weight548.264827575
IUPAC Name(2R,3R,4S,5S,6S)-6-carboxy-N-(2-{4-[(1Z)-1,2-diphenylbut-1-en-1-yl]phenoxy}ethyl)-3,4,5-trihydroxy-N,N-dimethyloxan-2-aminium
Traditional Nametamoxifen N-glucuronide
CAS Registry NumberNot Available
SMILES
CC\C(=C(/C1=CC=CC=C1)C1=CC=C(OCC[N+](C)(C)[C@@H]2O[C@@H]([C@@H](O)[C@H](O)[C@H]2O)C(O)=O)C=C1)C1=CC=CC=C1
InChI Identifier
InChI=1S/C32H37NO7/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)39-20-19-33(2,3)31-29(36)27(34)28(35)30(40-31)32(37)38/h5-18,27-31,34-36H,4,19-20H2,1-3H3/p+1/b26-25-/t27-,28-,29+,30-,31+/m0/s1
InChI KeyInChIKey=UKFQQYJAYUAYES-DTMHFWPESA-O
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as stilbene glycosides. These are compounds structurally characterized by the presence of a carbohydrate moiety glycosidically linked to the stilbene skeleton.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassStilbenes
Sub ClassStilbene glycosides
Direct ParentStilbene glycosides
Alternative Parents
Substituents
  • Stilbene glycoside
  • Pyranoid amino acid
  • 1-n-glucuronide
  • N-glucuronide
  • Glucuronic acid or derivatives
  • Diphenylmethane
  • N-glycosyl compound
  • Glycosyl compound
  • Pyran carboxylic acid
  • Pyran carboxylic acid or derivatives
  • Phenylpropene
  • Phenylpropane
  • Phenol ether
  • Choline
  • Beta-hydroxy acid
  • Alkyl aryl ether
  • Benzenoid
  • Pyran
  • Oxane
  • Hydroxy acid
  • Saccharide
  • Monocyclic benzene moiety
  • Quaternary ammonium salt
  • Secondary alcohol
  • Polyol
  • Hemiaminal
  • 1,2-diol
  • Oxacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Ether
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Alcohol
  • Organic cation
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Drug metabolite
Biofunction
  • Waste products
ApplicationNot Available
Cellular locations
  • Cytoplasm
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 Solubility0.0029 mg/mLALOGPS
logP2.46ALOGPS
logP0.095ChemAxon
logS-5.3ALOGPS
pKa (Strongest Acidic)3.18ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area116.45 Å2ChemAxon
Rotatable Bond Count10ChemAxon
Refractivity171.87 m3·mol-1ChemAxon
Polarizability59.48 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
Pathways
NameSMPDB LinkKEGG Link
Tamoxifen Metabolism PathwaySMP00606Not Available
Tamoxifen PathwaySMP00471Not Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDDBMET01004
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB60616
Metagene LinkHMDB60616
METLIN IDNot Available
PubChem Compound5460873
PDB IDNot Available
ChEBI ID32663
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available