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Record Information
Version3.6
Creation Date2008-08-06 16:08:07 UTC
Update Date2017-03-02 21:28:18 UTC
HMDB IDHMDB06766
Secondary Accession NumbersNone
Metabolite Identification
Common NameEstriol-16-Glucuronide
DescriptionEstriol-16-glucuronide is a glucuronide derivative of the steroid estriol where the glucuronic acid is attached to the 16-hydroxyl group of Estriol. 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. Estriol (also known as oestriol) is one of the three main estrogens produced by the human body. It is only produced in significant amounts during pregnancy as it is made by the placenta.
Structure
Thumb
Synonyms
ValueSource
16alpha,17beta-Estriol 16-(beta-D-glucuronide)Kegg
16a,17b-Estriol 16-(b-D-glucuronide)Generator
16α,17β-estriol 16-(β-D-glucuronide)Generator
16-Glucuronide-estriolHMDB
16alpha,17beta-Estriol 16-(beta-delta-glucuronide)HMDB
Estriol-16 alpha-(beta-D-glucuronide)MeSH
Estriol-16 alpha-(beta-D-glucuronide), sodium saltMeSH
Estriol-16-(beta-D-glucuronide), (16beta,17beta)-isomerMeSH
Estriol-16-glucosiduronateMeSH
Oestriol-16alpha-glucuronideMeSH
3,17 beta-Dihydroxy-1,3,5(10)-estratrien-16 alpha-yl-beta-D-glucopyranosiduronic acidMeSH
Estriol-16alpha-glucuronideMeSH
Estriol-16 alpha-glucuronideMeSH
Chemical FormulaC24H32O9
Average Molecular Weight464.5055
Monoisotopic Molecular Weight464.204632622
IUPAC Name(2S,3S,4S,5R,6R)-6-{[(1S,10R,11S,13R,14R,15S)-5,14-dihydroxy-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2(7),3,5-trien-13-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
Traditional Name(2S,3S,4S,5R,6R)-6-{[(1S,10R,11S,13R,14R,15S)-5,14-dihydroxy-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2(7),3,5-trien-13-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
CAS Registry Number1852-50-2
SMILES
C[C@]12CC[C@H]3[C@@H](CCC4=C3C=CC(O)=C4)[C@@H]1C[C@@H](O[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O)[C@@H]2O
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(21(24)29)32-23-19(28)17(26)18(27)20(33-23)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 KeyFQYGGFDZJFIDPU-JRSYHJKYSA-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
  • 17-hydroxysteroid
  • Hydroxysteroid
  • 1-o-glucuronide
  • Phenanthrene
  • O-glucuronide
  • Glucuronic acid or derivatives
  • Hexose monosaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • Tetralin
  • Beta-hydroxy acid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Benzenoid
  • Hydroxy acid
  • Pyran
  • Monosaccharide
  • Oxane
  • Cyclic alcohol
  • Secondary alcohol
  • Acetal
  • Organoheterocyclic compound
  • Oxacycle
  • Carboxylic acid
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Polyol
  • Alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Drug 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 Solubility1.05 mg/mLALOGPS
logP1.03ALOGPS
logP1.22ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)3.46ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area156.91 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity113.55 m3·mol-1ChemAxon
Polarizability48.42 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 Available
Normal
    details
    UrineDetected and Quantified9.8 +/- 0.16 umol/mmol creatinineAdult (>18 years old)BothNormal details
    Abnormal Concentrations
    BiofluidStatusValueAgeSexConditionReferenceDetails
    UrineDetected and Quantified1.58 +/- 0.86 umol/mmol creatinineAdult (>18 years old)FemalePregnancy details
    Associated Disorders and Diseases
    Disease References
    Pregnancy
    1. Yang YJ, Lee J, Choi MH, Chung BC: Direct determination of estriol 3- and 16-glucuronides in pregnancy urine by column-switching liquid chromatography with electrospray tandem mass spectrometry. Biomed Chromatogr. 2003 Jun;17(4):219-25. [PubMed:12833386 ]
    Associated OMIM IDsNone
    DrugBank IDNot Available
    DrugBank Metabolite IDDBMET00577
    Phenol Explorer Compound IDNot Available
    Phenol Explorer Metabolite IDNot Available
    FoodDB IDFDB024069
    KNApSAcK IDNot Available
    Chemspider ID109041
    KEGG Compound IDC05504
    BioCyc IDBeta-D-Glucuronides
    BiGG ID45936
    Wikipedia LinkNot Available
    NuGOwiki LinkHMDB06766
    Metagene LinkHMDB06766
    METLIN IDNot Available
    PubChem Compound122281
    PDB IDNot Available
    ChEBI IDNot Available
    References
    Synthesis ReferenceNot Available
    Material Safety Data Sheet (MSDS)Download (PDF)
    General References
    1. Lampinen-Salomonsson M, Bondesson U, Petersson C, Hedeland M: Differentiation of estriol glucuronide isomers by chemical derivatization and electrospray tandem mass spectrometry. Rapid Commun Mass Spectrom. 2006;20(9):1429-40. [PubMed:16586468 ]

    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
    Reactions
    Uridine diphosphate glucuronic acid + Estriol → Uridine 5'-diphosphate + Estriol-16-Glucuronidedetails
    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
    Reactions
    Uridine diphosphate glucuronic acid + Estriol → Uridine 5'-diphosphate + Estriol-16-Glucuronidedetails
    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
    Reactions
    Uridine diphosphate glucuronic acid + Estriol → Uridine 5'-diphosphate + Estriol-16-Glucuronidedetails
    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:
    UGT2B10
    Uniprot ID:
    P36537
    Molecular weight:
    60773.485
    Reactions
    Uridine diphosphate glucuronic acid + Estriol → Uridine 5'-diphosphate + Estriol-16-Glucuronidedetails
    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
    Reactions
    Uridine diphosphate glucuronic acid + Estriol → Uridine 5'-diphosphate + Estriol-16-Glucuronidedetails
    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
    Reactions
    Uridine diphosphate glucuronic acid + Estriol → Uridine 5'-diphosphate + Estriol-16-Glucuronidedetails
    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
    Reactions
    Uridine diphosphate glucuronic acid + Estriol → Uridine 5'-diphosphate + Estriol-16-Glucuronidedetails
    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
    Reactions
    Uridine diphosphate glucuronic acid + Estriol → Uridine 5'-diphosphate + Estriol-16-Glucuronidedetails
    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
    Reactions
    Uridine diphosphate glucuronic acid + Estriol → Uridine 5'-diphosphate + Estriol-16-Glucuronidedetails
    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
    Reactions
    Uridine diphosphate glucuronic acid + Estriol → Uridine 5'-diphosphate + Estriol-16-Glucuronidedetails
    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
    Reactions
    Uridine diphosphate glucuronic acid + Estriol → Uridine 5'-diphosphate + Estriol-16-Glucuronidedetails
    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
    Reactions
    Uridine diphosphate glucuronic acid + Estriol → Uridine 5'-diphosphate + Estriol-16-Glucuronidedetails
    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
    Reactions
    Uridine diphosphate glucuronic acid + Estriol → Uridine 5'-diphosphate + Estriol-16-Glucuronidedetails
    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
    Reactions
    Uridine diphosphate glucuronic acid + Estriol → Uridine 5'-diphosphate + Estriol-16-Glucuronidedetails
    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
    Reactions
    Uridine diphosphate glucuronic acid + Estriol → Uridine 5'-diphosphate + Estriol-16-Glucuronidedetails
    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
    Reactions
    Uridine diphosphate glucuronic acid + Estriol → Uridine 5'-diphosphate + Estriol-16-Glucuronidedetails
    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
    Reactions
    Uridine diphosphate glucuronic acid + Estriol → Uridine 5'-diphosphate + Estriol-16-Glucuronidedetails
    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
    Reactions
    Uridine diphosphate glucuronic acid + Estriol → Uridine 5'-diphosphate + Estriol-16-Glucuronidedetails
    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