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Record Information
Version3.6
Creation Date2013-07-22 19:49:26 UTC
Update Date2016-02-11 08:18:51 UTC
HMDB IDHMDB61125
Secondary Accession NumbersNone
Metabolite Identification
Common Name4-Hydroxytamoxifen-O-glucuronide
Description4-Hydroxytamoxifen-O-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
SynonymsNot Available
Chemical FormulaC32H37NO8
Average Molecular Weight563.6381
Monoisotopic Molecular Weight563.251917165
IUPAC Name(2R,3R,4R,5S)-6-{4-[(1Z)-1-{4-[2-(dimethylamino)ethoxy]phenyl}-2-phenylbut-1-en-1-yl]phenoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
Traditional Name(2R,3R,4R,5S)-6-{4-[(1Z)-1-{4-[2-(dimethylamino)ethoxy]phenyl}-2-phenylbut-1-en-1-yl]phenoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
CAS Registry NumberNot Available
SMILES
CC\C(=C(/C1=CC=C(OCCN(C)C)C=C1)C1=CC=C(OC2O[C@H]([C@H](O)[C@@H](O)[C@@H]2O)C(O)=O)C=C1)C1=CC=CC=C1
InChI Identifier
InChI=1/C32H37NO8/c1-4-25(20-8-6-5-7-9-20)26(21-10-14-23(15-11-21)39-19-18-33(2)3)22-12-16-24(17-13-22)40-32-29(36)27(34)28(35)30(41-32)31(37)38/h5-17,27-30,32,34-36H,4,18-19H2,1-3H3,(H,37,38)/b26-25-/t27-,28-,29+,30-,32?/s2
InChI KeyInChIKey=SSRNQFUJUAOPJD-KBYSETRVNA-N
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
  • Fatty acyl glycoside
  • Phenolic glycoside
  • O-glucuronide
  • 1-o-glucuronide
  • Glucuronic acid or derivatives
  • Diphenylmethane
  • Alkyl glycoside
  • O-glycosyl compound
  • Glycosyl compound
  • Pyran carboxylic acid
  • Pyran carboxylic acid or derivatives
  • Phenylpropene
  • Phenylpropane
  • Phenol ether
  • Beta-hydroxy acid
  • Alkyl aryl ether
  • Fatty acyl
  • Benzenoid
  • Pyran
  • Oxane
  • Monosaccharide
  • Hydroxy acid
  • Monocyclic benzene moiety
  • Tertiary aliphatic amine
  • Tertiary amine
  • Secondary alcohol
  • Polyol
  • 1,2-diol
  • Oxacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Ether
  • Carboxylic acid
  • Carboxylic acid derivative
  • Acetal
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Alcohol
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
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 Solubility0.025 mg/mLALOGPS
logP4.17ALOGPS
logP1.37ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)2.93ChemAxon
pKa (Strongest Basic)8.76ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area128.92 Å2ChemAxon
Rotatable Bond Count11ChemAxon
Refractivity162.42 m3·mol-1ChemAxon
Polarizability61.05 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
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
PathwaysNot 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 IDDBMET00739
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 LinkHMDB61125
Metagene LinkHMDB61125
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available