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Record Information
Version3.6
Creation Date2008-09-16 08:25:18 UTC
Update Date2017-08-16 07:05:33 UTC
HMDB IDHMDB0010354
Secondary Accession Numbers
  • HMDB10354
Metabolite Identification
Common Name16-alpha,17-beta-estriol 17-beta-D-glucuronide
Description16-alpha,17-beta-estriol 17-beta-D-glucuronide is a natural human metabolite of 16alpha,17beta-estriol 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
Estra-1,3,5(10)-triene-3,16alpha,17beta-triol 17-D-glucuronideHMDB
Estra-1,3,5(10)-triene-3,16alpha,17beta-triol 17-D-glucuronosideHMDB
Estra-1,3,5(10)-triene-3,16alpha,17beta-triol 17-delta-glucuronideHMDB
Estra-1,3,5(10)-triene-3,16alpha,17beta-triol 17-delta-glucuronosideHMDB
Estriol 17beta-(beta-D-glucuronide)HMDB
Estriol 17beta-(beta-delta-glucuronide)HMDB
Estriol 17beta-monoglucuronideHMDB
Chemical FormulaC24H32O9
Average Molecular Weight464.5055
Monoisotopic Molecular Weight464.204632622
IUPAC Name(2S,3S,4S,5R,6S)-6-{[(1S,10R,11S,13R,14R,15S)-5,13-dihydroxy-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2(7),3,5-trien-14-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
Traditional Name(2S,3S,4S,5R,6S)-6-{[(1S,10R,11S,13R,14R,15S)-5,13-dihydroxy-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2(7),3,5-trien-14-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
CAS Registry Number7219-89-8
SMILES
[H][C@@]12C[C@@H](O)[C@H](O[C@@]3([H])O[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(O)C=C3
InChI Identifier
InChI=1S/C24H32O9/c1-24-7-6-13-12-5-3-11(25)8-10(12)2-4-14(13)15(24)9-16(26)21(24)33-23-19(29)17(27)18(28)20(32-23)22(30)31/h3,5,8,13-21,23,25-29H,2,4,6-7,9H2,1H3,(H,30,31)/t13-,14-,15+,16-,17+,18+,19-,20+,21+,23-,24+/m1/s1
InChI KeyCZGFLAQOJPXVRV-JRSYHJKYSA-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
  • Estrogen-skeleton
  • 3-hydroxysteroid
  • Estrane-skeleton
  • Hydroxysteroid
  • 16-alpha-hydroxysteroid
  • 16-hydroxysteroid
  • 1-o-glucuronide
  • O-glucuronide
  • Phenanthrene
  • Glucuronic acid or derivatives
  • Hexose monosaccharide
  • O-glycosyl compound
  • Glycosyl compound
  • Tetralin
  • Beta-hydroxy acid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Benzenoid
  • Pyran
  • Oxane
  • Monosaccharide
  • Hydroxy acid
  • Cyclic alcohol
  • Secondary alcohol
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Acetal
  • Monocarboxylic acid or derivatives
  • Alcohol
  • Organooxygen compound
  • Organic oxygen compound
  • Organic oxide
  • Carbonyl group
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
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 Solubility1.07 mg/mLALOGPS
logP1.01ALOGPS
logP1.22ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)3.55ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area156.91 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity113.55 m3·mol-1ChemAxon
Polarizability48.84 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot 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 IDDBMET00603
      Phenol Explorer Compound IDNot Available
      Phenol Explorer Metabolite IDNot Available
      FoodDB IDFDB027506
      KNApSAcK IDNot Available
      Chemspider IDNot Available
      KEGG Compound IDC11346
      BioCyc IDBeta-D-Glucuronides
      BiGG IDNot Available
      Wikipedia LinkNot Available
      NuGOwiki LinkHMDB0010354
      METLIN IDNot Available
      PubChem Compound53480453
      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 has glucuronidating capacity with steroid substrates such as 5-beta-androstane 3-alpha,17-beta-diol, estradiol, ADT, eugenol and bile acids. Only isoform 1 seems to be active.
      Gene Name:
      UGT2B28
      Uniprot ID:
      Q9BY64
      Molecular weight:
      38742.9
      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:
      UDPGTs are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isozyme displays activity toward several classes of xenobiotic substrates, including simple phenolic compounds, 7-hydroxylated coumarins, flavonoids, anthraquinones, and certain drugs and their hydroxylated metabolites. It also catalyzes the glucuronidation of endogenous estrogens and androgens.
      Gene Name:
      UGT2B15
      Uniprot ID:
      P54855
      Molecular weight:
      61035.815
      General function:
      Involved in transferase activity, transferring hexosyl groups
      Specific function:
      UDP-glucuronosyltransferases catalyze phase II biotransformation reactions in which lipophilic substrates are conjugated with glucuronic acid to increase water solubility and enhance excretion. They are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. Active on odorants and seems to be involved in olfaction; it could help clear lipophilic odorant molecules from the sensory epithelium.
      Gene Name:
      UGT2A1
      Uniprot ID:
      Q9Y4X1
      Molecular weight:
      60771.605
      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.
      Gene Name:
      UGT1A8
      Uniprot ID:
      Q9HAW9
      Molecular weight:
      59741.035
      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.
      Gene Name:
      UGT1A3
      Uniprot ID:
      P35503
      Molecular weight:
      60337.835
      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:
      UGT1A10
      Uniprot ID:
      Q9HAW8
      Molecular weight:
      59809.075
      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. The major substrates of this isozyme are eugenol > 4-methylumbelliferone > dihydrotestosterone (DHT) > androstane-3-alpha,17-beta-diol (3-alpha-diol) > testosterone > androsterone (ADT).
      Gene Name:
      UGT2B17
      Uniprot ID:
      O75795
      Molecular weight:
      61094.915
      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:
      UGT1A5
      Uniprot ID:
      P35504
      Molecular weight:
      60070.565
      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 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:
      UGT1A7
      Uniprot ID:
      Q9HAW7
      Molecular weight:
      59818.315
      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
      General function:
      Involved in transferase activity, transferring hexosyl groups
      Specific function:
      UDP-glucuronosyltransferases catalyze phase II biotransformation reactions in which lipophilic substrates are conjugated with glucuronic acid to increase water solubility and enhance excretion. They are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds (By similarity).
      Gene Name:
      UGT2A3
      Uniprot ID:
      Q6UWM9
      Molecular weight:
      60253.94
      General function:
      Involved in transferase activity, transferring hexosyl groups
      Specific function:
      Not Available
      Gene Name:
      UGT1A10
      Uniprot ID:
      Q5DT02
      Molecular weight:
      59809.1
      General function:
      Involved in transferase activity, transferring hexosyl groups
      Specific function:
      Not Available
      Gene Name:
      UGT1A8
      Uniprot ID:
      Q5DSZ6
      Molecular weight:
      59741.0
      General function:
      Involved in transferase activity, transferring hexosyl groups
      Specific function:
      Not Available
      Gene Name:
      UGT1A7
      Uniprot ID:
      Q5DSZ7
      Molecular weight:
      59818.3