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Showing Compound 17b-Estradiol 3-glucuronide (FDB021792)

Record Information
Version1.0
Creation date2011-04-08 19:28:37 UTC
Update date2019-11-26 03:20:52 UTC
Primary IDFDB021792
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name17b-Estradiol 3-glucuronide
DescriptionEstradiol glucuronide is believed to play important roles in the mechanism of 17beta-estradiol(E2)-mediated tumor formation. Conjugation with glucuronic acid lowers tissue levels by facilitating excretion.The heterotropic activation by daidzein appears to be specific for the glucuronidation of E2 because daidzein did not affect the glucuronidation of the 2- and 4-hydroxy metabolites of E2. (PMID: 16598814) [HMDB]
CAS Number15270-30-1
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
17beta-Estradiol 3-(beta-D-glucuronide)ChEBI
17beta-Estradiol 3-glucuronideChEBI
Estradiol-17beta 3-glucuronideChEBI
Estradiol-3-glucuronideChEBI
17b-Estradiol 3-(b-D-glucuronide)Generator
17Β-estradiol 3-(β-D-glucuronide)Generator
17b-Estradiol 3-glucuronideGenerator
17Β-estradiol 3-glucuronideGenerator
Estradiol-17b 3-glucuronideGenerator
Estradiol-17β 3-glucuronideGenerator
17-b-Estradiol-3-glucuronideGenerator
17-Β-estradiol-3-glucuronideGenerator
(17beta)-17-Hydroxyestra-1,3,5(10)-trien-3-yl beta-D-glucopyranosiduronic acidHMDB
(17Β)-17-hydroxyestra-1,3,5(10)-trien-3-yl β-D-glucopyranosiduronic acidHMDB
17beta-Estradiol 3-glucosiduronateHMDB
17Β-estradiol 3-glucosiduronateHMDB
Estradiol 3-glucosiduronateHMDB
Estradiol 3-glucuronideHMDB
Estradiol-17beta-3-(beta-D-glucuronide)HMDB
Estradiol-17β-3-(β-D-glucuronide)HMDB
17-beta-Estradiol 3-glucuronidemanual
17-beta-Estradiol 3-O-glucuronidemanual
17-beta-Estradiol-3-glucuronidemanual
17b-Estra-1,3,5(10)-triene-3,17-diol 3-O-b-D-glucuronopyranosidemanual
17beta-Estradiol 3-(beta-delta-glucuronide)HMDB
17beta-Estradiol 3-glucosiduronic acidHMDB
17beta-Estradiol-3-glucuronideHMDB
17beta-Hydroxyestra-1,3,5(10)-trien-3-yl beta-D-glucopyranosiduronic acidHMDB
17beta-Hydroxyestra-1,3,5(10)-trien-3-yl beta-delta-glucopyranosiduronic acidHMDB
beta-Estradiol 3-β-D-glucuronideHMDB
Estra-1,3,5(10)-triene-3,17beta-diol 3-D-glucuronideHMDB
Estra-1,3,5(10)-triene-3,17beta-diol 3-delta-glucuronideHMDB
Estradiol glucuronideHMDB
Estradiol-17-beta-3-glucuronideHMDB
Predicted Properties
PropertyValueSource
Water Solubility0.35 g/LALOGPS
logP1.46ALOGPS
logP1.8ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)3.3ChemAxon
pKa (Strongest Basic)-0.88ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area136.68 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity111.92 m³·mol⁻¹ChemAxon
Polarizability48.13 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC24H32O8
IUPAC name(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[(1S,10R,11S,14S,15S)-14-hydroxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-trien-5-yl]oxy}oxane-2-carboxylic acid
InChI IdentifierInChI=1S/C24H32O8/c1-24-9-8-14-13-5-3-12(10-11(13)2-4-15(14)16(24)6-7-17(24)25)31-23-20(28)18(26)19(27)21(32-23)22(29)30/h3,5,10,14-21,23,25-28H,2,4,6-9H2,1H3,(H,29,30)/t14-,15-,16+,17+,18+,19+,20-,21+,23-,24+/m1/s1
InChI KeyMUOHJTRCBBDUOW-QXYWQCSFSA-N
Isomeric SMILES[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@]1([H])C3=CC=C(O[C@@H]4O[C@@H]([C@@H](O)[C@H](O)[C@H]4O)C(O)=O)C=C3CC[C@@]21[H]
Average Molecular Weight448.5061
Monoisotopic Molecular Weight448.209718
Classification
Description Belongs to the class of organic compounds known as steroid glucuronide conjugates. These are sterol lipids containing a glucuronide moiety linked to the steroid skeleton.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassSteroidal glycosides
Direct ParentSteroid glucuronide conjugates
Alternative Parents
Substituents
  • Steroid-glucuronide-skeleton
  • Estrane-skeleton
  • Hydroxysteroid
  • 17-hydroxysteroid
  • Fatty acyl glycoside
  • Phenolic glycoside
  • Fatty acyl glycoside of mono- or disaccharide
  • 1-o-glucuronide
  • O-glucuronide
  • Phenanthrene
  • Glucuronic acid or derivatives
  • Alkyl glycoside
  • O-glycosyl compound
  • Glycosyl compound
  • Tetralin
  • Beta-hydroxy acid
  • Fatty acyl
  • Pyran
  • Benzenoid
  • Oxane
  • Monosaccharide
  • Hydroxy acid
  • Cyclic alcohol
  • Secondary alcohol
  • Polyol
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Carboxylic acid
  • Acetal
  • Monocarboxylic acid or derivatives
  • Oxacycle
  • Alcohol
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Carbonyl group
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
OntologyNo ontology term
Physico-Chemical Properties
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
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS17b-Estradiol 3-glucuronide, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS17b-Estradiol 3-glucuronide, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0000900000-dbce777edf435a424ee42021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-2222900000-cdf3987eca3a9e28d21a2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0kgk-6193300000-8d16b4b751613c15d0cf2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0030900000-fe10dd4aa1baa46d3dde2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a5a-0245900000-bb81ada0e7df1ba06f1a2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052b-1961000000-9417e71bf8ebf04449162021-09-24View Spectrum
NMRNot Available
ChemSpider ID18667985
ChEMBL IDNot Available
KEGG Compound IDC05503
Pubchem Compound ID13783824
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB06224
CRC / DFC (Dictionary of Food Compounds) IDBBB24-E:FQY19-K
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID2304841
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 2B10UGT2B10P36537
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
Pathways
NameSMPDB LinkKEGG Link
Androgen and Estrogen MetabolismSMP00068 map00150
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference