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Record Information
Version3.6
Creation Date2008-09-16 08:31:36 UTC
Update Date2016-02-11 01:18:43 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
Estradiol glucuronide sulfuric acidGenerator
Estradiol glucuronide sulphateGenerator
Estradiol glucuronide sulphuric acidGenerator
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 KeyInChIKey=VRMSCBRLZUCJBX-QXYWQCSFSA-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
  • 3-sulfated steroid
  • Sulfated steroid skeleton
  • Estrane-skeleton
  • Phenanthrene
  • O-glucuronide
  • 1-o-glucuronide
  • Glucuronic acid or derivatives
  • O-glycosyl compound
  • Glycosyl compound
  • Tetralin
  • Pyran carboxylic acid
  • Pyran carboxylic acid or derivatives
  • Sulfuric acid monoester
  • Beta-hydroxy acid
  • Benzenoid
  • Sulfuric acid ester
  • Sulfate-ester
  • Pyran
  • Oxane
  • Monosaccharide
  • Hydroxy acid
  • Saccharide
  • Organic sulfuric acid or derivatives
  • Secondary alcohol
  • Polyol
  • 1,2-diol
  • Oxacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Acetal
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • 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
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 QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
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