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Record Information
Version3.6
Creation Date2008-09-16 08:31:36 UTC
Update Date2017-03-02 21:31:16 UTC
HMDB IDHMDB10358
Secondary Accession NumbersNone
Metabolite Identification
Common Name17-beta-estradiol 3-sulfate-17-(beta-D-glucuronide)
Description17-beta-estradiol 3-sulfate-17-(beta-D-glucuronide) is a natural human metabolite of 17beta-estradiol 3-sulfate generated in the liver by UDP glucuonyltransferase. Glucuronidation is used to assist in the excretion of toxic substances, drugs or other substances that cannot be used as an energy source. Glucuronic acid is attached via a glycosidic bond to the substance, and the resulting glucuronide, which has a much higher water solubility than the original substance, is eventually excreted by the kidneys.
Structure
Thumb
Synonyms
ValueSource
Estradiol 17beta-glucuronide 3-sulfateKegg
Estradiol 17b-glucuronide 3-sulfateGenerator
Estradiol 17b-glucuronide 3-sulfuric acidGenerator
Estradiol 17b-glucuronide 3-sulphateGenerator
Estradiol 17b-glucuronide 3-sulphuric acidGenerator
Estradiol 17beta-glucuronide 3-sulfuric acidGenerator
Estradiol 17beta-glucuronide 3-sulphateGenerator
Estradiol 17beta-glucuronide 3-sulphuric acidGenerator
Estradiol 17β-glucuronide 3-sulfateGenerator
Estradiol 17β-glucuronide 3-sulfuric acidGenerator
Estradiol 17β-glucuronide 3-sulphateGenerator
Estradiol 17β-glucuronide 3-sulphuric acidGenerator
17-b-Estradiol 3-sulfate-17-(b-D-glucuronide)Generator
17-b-Estradiol 3-sulfuric acid-17-(b-D-glucuronide)Generator
17-b-Estradiol 3-sulphate-17-(b-D-glucuronide)Generator
17-b-Estradiol 3-sulphuric acid-17-(b-D-glucuronide)Generator
17-beta-Estradiol 3-sulfuric acid-17-(beta-D-glucuronide)Generator
17-beta-Estradiol 3-sulphate-17-(beta-D-glucuronide)Generator
17-beta-Estradiol 3-sulphuric acid-17-(beta-D-glucuronide)Generator
17-β-estradiol 3-sulfate-17-(β-D-glucuronide)Generator
17-β-estradiol 3-sulfuric acid-17-(β-D-glucuronide)Generator
17-β-estradiol 3-sulphate-17-(β-D-glucuronide)Generator
17-β-estradiol 3-sulphuric acid-17-(β-D-glucuronide)Generator
17beta-Estradiol 3-sulfate-17-(beta-D-glucuronoside)HMDB
17beta-Estradiol 3-sulfate-17-(beta-delta-glucuronoside)HMDB
17beta-Estradiol 3-sulphate-17-(beta-D-glucuronoside)HMDB
17beta-Estradiol 3-sulphate-17-(beta-delta-glucuronoside)HMDB
Estra-1,3,5(10)-triene-3,17beta-diol 3-sulfate-17-D-glucuronideHMDB
Estra-1,3,5(10)-triene-3,17beta-diol 3-sulfate-17-D-glucuronosideHMDB
Estra-1,3,5(10)-triene-3,17beta-diol 3-sulfate-17-delta-glucuronideHMDB
Estra-1,3,5(10)-triene-3,17beta-diol 3-sulfate-17-delta-glucuronosideHMDB
Estra-1,3,5(10)-triene-3,17beta-diol 3-sulphate-17-D-glucuronideHMDB
Estra-1,3,5(10)-triene-3,17beta-diol 3-sulphate-17-D-glucuronosideHMDB
Estra-1,3,5(10)-triene-3,17beta-diol 3-sulphate-17-delta-glucuronideHMDB
Estra-1,3,5(10)-triene-3,17beta-diol 3-sulphate-17-delta-glucuronosideHMDB
Chemical FormulaC24H32O11S
Average Molecular Weight528.569
Monoisotopic Molecular Weight528.166532556
IUPAC Name(2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-{[(1S,10R,11S,14S,15S)-15-methyl-5-(sulfooxy)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2(7),3,5-trien-14-yl]oxy}oxane-2-carboxylic acid
Traditional Name(2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-{[(1S,10R,11S,14S,15S)-15-methyl-5-(sulfooxy)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2(7),3,5-trien-14-yl]oxy}oxane-2-carboxylic acid
CAS Registry NumberNot Available
SMILES
[H][C@@]12CC[C@H](O[C@@H]3O[C@@H]([C@@H](O)[C@H](O)[C@H]3O)C(O)=O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(OS(O)(=O)=O)C=C3
InChI Identifier
InChI=1S/C24H32O11S/c1-24-9-8-14-13-5-3-12(35-36(30,31)32)10-11(13)2-4-15(14)16(24)6-7-17(24)33-23-20(27)18(25)19(26)21(34-23)22(28)29/h3,5,10,14-21,23,25-27H,2,4,6-9H2,1H3,(H,28,29)(H,30,31,32)/t14-,15-,16+,17+,18+,19+,20-,21+,23-,24+/m1/s1
InChI KeyVRMSCBRLZUCJBX-QXYWQCSFSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as steroidal glycosides. These are sterol lipids containing a carbohydrate moiety glycosidically linked to the steroid skeleton.
KingdomChemical entities
Super ClassOrganic compounds
ClassLipids and lipid-like molecules
Sub ClassSteroids and steroid derivatives
Direct ParentSteroidal glycosides
Alternative Parents
Substituents
  • Steroidal glycoside
  • Sulfated steroid skeleton
  • Estrane-skeleton
  • 1-o-glucuronide
  • O-glucuronide
  • Phenanthrene
  • Glucuronic acid or derivatives
  • Glycosyl compound
  • O-glycosyl compound
  • Arylsulfate
  • Tetralin
  • Beta-hydroxy acid
  • Sulfate-ester
  • Sulfuric acid monoester
  • Hydroxy acid
  • Monosaccharide
  • Oxane
  • Benzenoid
  • Pyran
  • Sulfuric acid ester
  • Organic sulfuric acid or derivatives
  • Secondary alcohol
  • Organoheterocyclic compound
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Acetal
  • Carboxylic acid derivative
  • Polyol
  • Carboxylic acid
  • Hydrocarbon derivative
  • Alcohol
  • Organic oxide
  • Organooxygen compound
  • Carbonyl group
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Drug or steroid metabolite
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
  • Waste products
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Cytoplasm
  • Extracellular
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.25 mg/mLALOGPS
logP0.25ALOGPS
logP0.16ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)-1.7ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area180.05 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity122.18 m3·mol-1ChemAxon
Polarizability53.25 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
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 IDDBMET00606
      Phenol Explorer Compound IDNot Available
      Phenol Explorer Metabolite IDNot Available
      FoodDB IDFDB027510
      KNApSAcK IDNot Available
      Chemspider ID4445182
      KEGG Compound IDC11289
      BioCyc IDNot Available
      BiGG IDNot Available
      Wikipedia LinkNot Available
      NuGOwiki LinkHMDB10358
      Metagene LinkHMDB10358
      METLIN IDNot Available
      PubChem Compound5281895
      PDB IDNot Available
      ChEBI IDNot Available
      References
      Synthesis ReferenceNot Available
      Material Safety Data Sheet (MSDS)Not Available
      General ReferencesNot Available

      Enzymes

      General function:
      Involved in transferase activity, transferring hexosyl groups
      Specific function:
      UDPGTs are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isozyme is active on polyhydroxylated estrogens (such as estriol, 4-hydroxyestrone and 2-hydroxyestriol) and xenobiotics (such as 4-methylumbelliferone, 1-naphthol, 4-nitrophenol, 2-aminophenol, 4-hydroxybiphenyl and menthol). It is capable of 6 alpha-hydroxyglucuronidation of hyodeoxycholic acid.
      Gene Name:
      UGT2B4
      Uniprot ID:
      P06133
      Molecular weight:
      60512.035
      General function:
      Involved in transferase activity, transferring hexosyl groups
      Specific function:
      UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate.
      Gene Name:
      UGT1A4
      Uniprot ID:
      P22310
      Molecular weight:
      60024.535
      General function:
      Involved in transferase activity, transferring hexosyl groups
      Specific function:
      UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. Its unique specificity for 3,4-catechol estrogens and estriol suggests it may play an important role in regulating the level and activity of these potent and active estrogen metabolites. Is also active with androsterone, hyodeoxycholic acid and tetrachlorocatechol (in vitro).
      Gene Name:
      UGT2B7
      Uniprot ID:
      P16662
      Molecular weight:
      60720.15
      General function:
      Involved in transferase activity, transferring hexosyl groups
      Specific function:
      UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
      Gene Name:
      UGT1A1
      Uniprot ID:
      P22309
      Molecular weight:
      59590.91
      General function:
      Involved in transferase activity, transferring hexosyl groups
      Specific function:
      UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform has specificity for phenols.
      Gene Name:
      UGT1A9
      Uniprot ID:
      O60656
      Molecular weight:
      59940.495
      General function:
      Involved in transferase activity, transferring hexosyl groups
      Specific function:
      UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform has specificity for phenols.
      Gene Name:
      UGT1A6
      Uniprot ID:
      P19224
      Molecular weight:
      60750.215
      General function:
      Involved in transferase activity, transferring hexosyl groups
      Specific function:
      UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds.
      Gene Name:
      UGT2B11
      Uniprot ID:
      O75310
      Molecular weight:
      61037.8
      General function:
      Involved in hydrolase activity, hydrolyzing O-glycosyl compounds
      Specific function:
      Plays an important role in the degradation of dermatan and keratan sulfates.
      Gene Name:
      GUSB
      Uniprot ID:
      P08236
      Molecular weight:
      74731.46