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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2008-09-16 08:28:35 UTC
Update Date2018-05-18 01:44:44 UTC
HMDB IDHMDB0010356
Secondary Accession Numbers
  • HMDB10356
Metabolite Identification
Common NameEstriol 3-sulfate 16-glucuronide
DescriptionEstriol 3-sulfate 16-glucuronide is a natural human metabolite of Estriol 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
(16alpha,17beta)-17-Hydroxy-3-(sulfooxy)estra-1,3,5(10)-trien-16-yl-beta-D-glucopyranosiduronic acidHMDB
(16alpha,17beta)-17-Hydroxy-3-(sulfooxy)estra-1,3,5(10)-trien-16-yl-beta-delta-glucopyranosiduronic acidHMDB
Estriol 3-sulfate 16-glucuronosideHMDB
Estriol 3-sulfate 16alpha-glucuronideHMDB
Estriol 3-sulfate 16alpha-glucuronosideHMDB
Estriol 3-sulphate 16-glucuronideHMDB
Estriol 3-sulphate 16-glucuronosideHMDB
Estriol 3-sulphate 16alpha-glucuronideHMDB
Estriol 3-sulphate 16alpha-glucuronosideHMDB
Estriol 3-sulfate 16-glucuronide, (16beta,17beta)-isomerMeSH
Estriol-3-sulfate 16-glucosiduronate, (16alpha)-isomerMeSH
Chemical FormulaC24H32O12S
Average Molecular Weight544.569
Monoisotopic Molecular Weight544.161447178
IUPAC Name(2S,3S,4S,5R)-3,4,5-trihydroxy-6-{[(1S,10R,11S,13R,14R,15S)-14-hydroxy-15-methyl-5-(sulfooxy)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2(7),3,5-trien-13-yl]oxy}oxane-2-carboxylic acid
Traditional Name(2S,3S,4S,5R)-3,4,5-trihydroxy-6-{[(1S,10R,11S,13R,14R,15S)-14-hydroxy-15-methyl-5-(sulfooxy)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2(7),3,5-trien-13-yl]oxy}oxane-2-carboxylic acid
CAS Registry Number4661-65-8
SMILES
[H][C@@]12C[C@@H](OC3O[C@@H]([C@@H](O)[C@H](O)[C@H]3O)C(O)=O)[C@H](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/C24H32O12S/c1-24-7-6-13-12-5-3-11(36-37(31,32)33)8-10(12)2-4-14(13)15(24)9-16(21(24)28)34-23-19(27)17(25)18(26)20(35-23)22(29)30/h3,5,8,13-21,23,25-28H,2,4,6-7,9H2,1H3,(H,29,30)(H,31,32,33)/t13-,14-,15+,16-,17+,18+,19-,20+,21+,23?,24+/m1/s1
InChI KeyATNWFRGUDKUYOG-SUPAOECSSA-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
  • Sulfated steroid skeleton
  • Estrane-skeleton
  • Hydroxysteroid
  • 17-hydroxysteroid
  • 1-o-glucuronide
  • O-glucuronide
  • Phenanthrene
  • Glucuronic acid or derivatives
  • Glycosyl compound
  • O-glycosyl compound
  • Arylsulfate
  • Tetralin
  • Beta-hydroxy acid
  • Hydroxy acid
  • Monosaccharide
  • Benzenoid
  • Sulfuric acid ester
  • Sulfate-ester
  • Oxane
  • Sulfuric acid monoester
  • Pyran
  • Cyclic alcohol
  • Organic sulfuric acid or derivatives
  • Secondary alcohol
  • Polyol
  • Carboxylic acid
  • Carboxylic acid derivative
  • Oxacycle
  • Acetal
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Carbonyl group
  • Organic oxide
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organooxygen compound
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

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 Solubility1.83 g/LALOGPS
logP0.01ALOGPS
logP-0.92ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)-1.7ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area200.28 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity123.54 m³·mol⁻¹ChemAxon
Polarizability54.16 ųChemAxon
Number of Rings5ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0570-6249350000-317fea4e7b62a27fcd79View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00di-3339016000-1e8cf725fc89c11b2b94View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0gdj-0009070000-daa124cbb6b8e2e3b51fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uy0-0159010000-937b11197960c05e4432View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uxr-0394000000-3dec314342d2e27ab531View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00kg-3306490000-5cba7d5ffaec99310c8fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014j-2239510000-640e9973f8698cd53bd5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-015i-9258000000-7173317347e8b38f90caView in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biospecimen Locations
  • Amniotic Fluid
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Amniotic FluidDetected and Quantified0.046 +/- 0.036 uMAdult (>18 years old)Both
Ambulant pregnancy
details
BloodDetected and Quantified0.11 +/- 0.08 uMAdult (>18 years old)Female
Ambulant pregnancy
details
UrineDetected and Quantified0.49 +/- 0.25 umol/mmol creatinineAdult (>18 years old)Both
Ambulant pregnancy
details
Associated Disorders and Diseases
Disease References
Pregnancy
  1. Andreolini F, Borra C, Caccamo F, Di Corcia A, Nicoletti I, Samperi R, Improta F: Estriol and its conjugates in late pregnancy determined by extraction with Carbopack B and liquid chromatography with fluorometric detection. Clin Chem. 1985 Oct;31(10):1698-702. [PubMed:2994907 ]
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB027508
KNApSAcK IDNot Available
Chemspider ID133283
KEGG Compound IDNot Available
BioCyc IDBeta-D-Glucuronides
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound151223
PDB IDNot Available
ChEBI ID88727
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.