Record Information
Version1.0
Creation date2011-09-21 01:25:30 UTC
Update date2015-07-21 06:59:08 UTC
Primary IDFDB027508
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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. [HMDB]
CAS Number4661-65-8
Structure
Thumb
Synonyms
SynonymSource
Estriol 3-sulfuric acid 16-glucuronideGenerator
Estriol 3-sulphate 16-glucuronideGenerator
Estriol 3-sulphuric acid 16-glucuronideGenerator
(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-glucuronosideHMDB
Estriol 3-sulphate 16alpha-glucuronideHMDB
Estriol 3-sulphate 16alpha-glucuronosideHMDB
Estriol 3-sulfate 16-glucuronide, (16beta,17beta)-isomerHMDB
Estriol-3-sulfate 16-glucosiduronate, (16alpha)-isomerHMDB
(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-2,4,6-trien-13-yl]oxy}oxane-2-carboxylateGenerator
(2S,3S,4S,5R)-3,4,5-Trihydroxy-6-{[(1S,10R,11S,13R,14R,15S)-14-hydroxy-15-methyl-5-(sulphooxy)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2,4,6-trien-13-yl]oxy}oxane-2-carboxylateGenerator
(2S,3S,4S,5R)-3,4,5-Trihydroxy-6-{[(1S,10R,11S,13R,14R,15S)-14-hydroxy-15-methyl-5-(sulphooxy)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2,4,6-trien-13-yl]oxy}oxane-2-carboxylic acidGenerator
Estriol 3-sulfate 16-glucuronideMeSH
(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
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC24H32O12S
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
InChI IdentifierInChI=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
Isomeric 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
Average Molecular Weight544.569
Monoisotopic Molecular Weight544.161447178
Classification
Description 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:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0570-6249350000-317fea4e7b62a27fcd79JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00di-3339016000-1e8cf725fc89c11b2b94JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0gdj-0009070000-daa124cbb6b8e2e3b51fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uy0-0159010000-937b11197960c05e4432JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uxr-0394000000-3dec314342d2e27ab531JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00kg-3306490000-5cba7d5ffaec99310c8fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014j-2239510000-640e9973f8698cd53bd5JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-015i-9258000000-7173317347e8b38f90caJSpectraViewer
ChemSpider ID133283
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID151223
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB10356
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
UDP-glucuronosyltransferase 2B28UGT2B28Q9BY64
UDP-glucuronosyltransferase 2B4UGT2B4P06133
UDP-glucuronosyltransferase 1-4UGT1A4P22310
UDP-glucuronosyltransferase 2B7UGT2B7P16662
UDP-glucuronosyltransferase 2B15UGT2B15P54855
UDP-glucuronosyltransferase 2A1UGT2A1Q9Y4X1
UDP-glucuronosyltransferase 1-1UGT1A1P22309
UDP-glucuronosyltransferase 1-9UGT1A9O60656
UDP-glucuronosyltransferase 1-8UGT1A8Q9HAW9
UDP-glucuronosyltransferase 1-3UGT1A3P35503
UDP-glucuronosyltransferase 1-10UGT1A10Q9HAW8
UDP-glucuronosyltransferase 2B17UGT2B17O75795
UDP-glucuronosyltransferase 1-6UGT1A6P19224
UDP-glucuronosyltransferase 1-5UGT1A5P35504
UDP-glucuronosyltransferase 2B11UGT2B11O75310
UDP-glucuronosyltransferase 1-7UGT1A7Q9HAW7
UDP-glucuronosyltransferase 2A3UGT2A3Q6UWM9
Beta-glucuronidaseGUSBP08236
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference