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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2008-09-15 17:17:33 UTC
Update Date2018-05-20 20:25:11 UTC
HMDB IDHMDB0010333
Secondary Accession Numbers
  • HMDB0010354
  • HMDB10333
  • HMDB10354
Metabolite Identification
Common NameEstriol-17-glucuronide
DescriptionEstriol-17-glucuronide, also known as estriol 17beta-(beta-D-glucuronide), is a member of the class of compounds known as steroidal glycosides. Steroidal glycosides are sterol lipids containing a carbohydrate moiety glycosidically linked to the steroid skeleton. Thus, estriol-17-glucuronide is considered to be a steroid conjugate lipid molecule. Estriol-17-glucuronide can be in urine and blood, as well as in human liver, kidney, and hepatic tissue tissues. Within the cell, estriol-17-glucuronide is primarily located in the cytoplasm, in the membrane (predicted from logP), and in the cell membrane. 16alpha,17beta-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
(16alpha,17beta)-3,16-Dihydroxyestra-1,3,5(10)-trien-17-yl beta-D-glucopyranosiduronic acidHMDB
(16alpha,17beta)-3,16-Dihydroxyestra-1,3,5(10)-trien-17-yl beta-delta-glucopyranosiduronic acidHMDB
17beta-(beta-D-Glucopyranuronosyloxy)estra-1,3,5(10)-triene-3,16alpha-diolHMDB
17beta-(beta-delta-Glucopyranuronosyloxy) estra-1,3,5(10)-triene-3,16alpha-diolHMDB
17beta-(beta-delta-Glucopyranuronosyloxy)estra-1,3,5(10)-triene-3,16alpha-diolHMDB
3,16alpha-Dihydroxyestra-1,3,5(10)-trien-17beta-yl glucopyranosiduronic acidHMDB
beta-D-Glucopyranosiduronic acid derivative OF estraneHMDB
beta-delta-Glucopyranosiduronic acid derivative OF estraneHMDB
Estriol 17-glucuronideHMDB
Estriol 17beta-(beta-D-glucuronide)HMDB
Estriol 17beta-glucuronideHMDB
Estriol 17beta-monoglucuronideHMDB
16-a,17-b-Estriol 17-b-D-glucuronideGenerator
16-α,17-β-estriol 17-β-D-glucuronideGenerator
Estriol 17β-(β-D-glucuronide)CAS
Estriol 17beta-(β-D-glucuronide)CAS
16α,17β-Estriol 17-(β-D-glucuronide)HMDB
16alpha,17beta-Estriol 17-(beta-D-glucuronide)HMDB
16-alpha,17-beta-Estriol 17-beta-D-glucuronideHMDB
Chemical FormulaC24H32O9
Average Molecular Weight464.511
Monoisotopic Molecular Weight464.20463261
IUPAC Name(2S,3S,4S,5R,6R)-6-{[(1S,10R,11S,13R,14R,15S)-5,13-dihydroxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-trien-14-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
Traditional Name(2S,3S,4S,5R,6R)-6-{[(1S,10R,11S,13R,14R,15S)-5,13-dihydroxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]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-FLVROIOLSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as steroidal glycosides. These are sterol lipids containing a carbohydrate moiety glycosidically linked to the steroid skeleton.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassSteroidal glycosides
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 Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

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 g/LALOGPS
logP1.22ChemAxon
pKa (Strongest Acidic)3.55ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area156.91 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity113.55 m³·mol⁻¹ChemAxon
Polarizability48.3 ųChemAxon
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
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not SpecifiedNot SpecifiedNormal
    details
    BloodExpected but not Quantified Not AvailableNot AvailableNormal
      details
      UrineExpected but not Quantified Not SpecifiedNot SpecifiedNormal
        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
          Phenol Explorer Compound IDNot Available
          FoodDB IDFDB027485
          KNApSAcK IDNot Available
          Chemspider ID4445190
          KEGG Compound IDC11346
          BioCyc IDNot Available
          BiGG IDNot Available
          Wikipedia LinkNot Available
          METLIN IDNot Available
          PubChem Compound151453
          PDB IDNot Available
          ChEBI IDNot Available
          References
          Synthesis ReferenceNot Available
          Material Safety Data Sheet (MSDS)Not Available
          General ReferencesNot Available

          Only showing the first 10 proteins. There are 21 proteins in total.

          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

          Only showing the first 10 proteins. There are 21 proteins in total.