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Record Information
Version3.6
Creation Date2013-07-22 19:49:21 UTC
Update Date2016-02-11 08:18:50 UTC
HMDB IDHMDB61124
Secondary Accession NumbersNone
Metabolite Identification
Common Name4-Hydroxytamoxifen-N-glucuronide
Description4-Hydroxytamoxifen-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
SynonymsNot Available
Chemical FormulaC30H33NO9
Average Molecular Weight551.5843
Monoisotopic Molecular Weight551.215531659
IUPAC Name(2R,3R,4R,5S)-3,4,5-trihydroxy-6-{[(2-{4-[(1E)-1-(4-hydroxyphenyl)-2-phenylbut-1-en-1-yl]phenoxy}ethyl)amino]oxy}oxane-2-carboxylic acid
Traditional Name(2R,3R,4R,5S)-3,4,5-trihydroxy-6-{[(2-{4-[(1E)-1-(4-hydroxyphenyl)-2-phenylbut-1-en-1-yl]phenoxy}ethyl)amino]oxy}oxane-2-carboxylic acid
CAS Registry NumberNot Available
SMILES
CC\C(=C(\C1=CC=C(O)C=C1)C1=CC=C(OCCNOC2O[C@H]([C@H](O)[C@@H](O)[C@@H]2O)C(O)=O)C=C1)C1=CC=CC=C1
InChI Identifier
InChI=1/C30H33NO9/c1-2-23(18-6-4-3-5-7-18)24(19-8-12-21(32)13-9-19)20-10-14-22(15-11-20)38-17-16-31-40-30-27(35)25(33)26(34)28(39-30)29(36)37/h3-15,25-28,30-35H,2,16-17H2,1H3,(H,36,37)/b24-23+/t25-,26-,27+,28-,30?/s2
InChI KeyInChIKey=ZGQCEPMGLPXICX-UTYMIQMWNA-N
Chemical Taxonomy
DescriptionThis compound 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
  • Glucuronic acid or derivatives
  • Diphenylmethane
  • O-hexosamine
  • Amino sugar
  • Pyran carboxylic acid
  • Pyran carboxylic acid or derivatives
  • Phenylpropene
  • Phenylpropane
  • Phenol ether
  • Amino saccharide
  • Phenol
  • Beta-hydroxy acid
  • Alkyl aryl ether
  • Benzenoid
  • Pyran
  • Oxane
  • Monosaccharide
  • Hydroxy acid
  • Saccharide
  • Monocyclic benzene moiety
  • Secondary alcohol
  • Polyol
  • 1,2-diol
  • Oxacycle
  • N-organohydroxylamine
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Ether
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • 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
  • Membrane (predicted from logP)
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 Solubility0.033 mg/mLALOGPS
logP3.42ALOGPS
logP2.07ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)2.93ChemAxon
pKa (Strongest Basic)4.37ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area157.94 Å2ChemAxon
Rotatable Bond Count11ChemAxon
Refractivity164.61 m3·mol-1ChemAxon
Polarizability58.53 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane (predicted from logP)
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 IDDBMET00738
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 LinkHMDB61124
Metagene LinkHMDB61124
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