Showing metabocard for Estrone glucuronide (LMDB00455)

IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-07-13 19:50:14 UTC
Update Date2016-08-01 19:11:18 UTC
LmdbLMDB00455
Secondary Accession NumbersNone
Metabolite Identification
Common NameEstrone glucuronide
DescriptionEstrone-glucuronide is the dominant metabolite of estradiol. Estrone glucuronide is formed by a UDP glucuronyltransferase (EC 2.4.1.17, UTP) reaction creating a much more water-soluble form of the hormone; glucuronides are the most abundant estrogen conjugates. Measurement of estrone-glucuronide is used as one reference method for determining ovulation (immunotubes are available for measuring urinary estrone glucuronide in conjunction with LH, one of the most advanced of ovulation prediction products). (PMID: 14742773 , 1755456 ).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Estrone 3-glucosiduronic acidChEBI
Estrone 3-glucuronideChEBI
Estrone beta-D-glucuronideChEBI
Estrone 3-glucosiduronateGenerator
Estrone b-D-glucuronideGenerator
Estrone β-D-glucuronideGenerator
Estrone beta-delta-glucuronideHMDB
Estrone-3-glucosiduronic acidHMDB
Estrone-3-glucuronideHMDB
Estrone-3-glucosiduronateHMDB
Chemical FormulaC24H30O8
Average Molecular Weight446.4902
Monoisotopic Molecular Weight446.194067936
IUPAC Name(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[(1S,10R,11S,15S)-15-methyl-14-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2,4,6-trien-5-yl]oxy}oxane-2-carboxylic acid
Traditional Nameestrone-3-glucuronide
CAS Registry Number2479-90-5
SMILES
[H][C@@]12CCC(=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]
InChI Identifier
InChI=1S/C24H30O8/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/h3,5,10,14-16,18-21,23,26-28H,2,4,6-9H2,1H3,(H,29,30)/t14-,15-,16+,18+,19+,20-,21+,23-,24+/m1/s1
InChI KeyFJAZVHYPASAQKM-JBAURARKSA-N
Chemical Taxonomy
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
  • 17-oxosteroid
  • Oxosteroid
  • Fatty acyl glycoside
  • Fatty acyl glycoside of mono- or disaccharide
  • Phenolic glycoside
  • 1-o-glucuronide
  • O-glucuronide
  • Phenanthrene
  • Glucuronic acid or derivatives
  • Alkyl glycoside
  • Glycosyl compound
  • O-glycosyl compound
  • Tetralin
  • Beta-hydroxy acid
  • Pyran
  • Fatty acyl
  • Oxane
  • Benzenoid
  • Monosaccharide
  • Hydroxy acid
  • Ketone
  • Secondary alcohol
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Acetal
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Carbonyl group
  • Alcohol
  • Organic oxide
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
StatusDetected but not Quantified
OriginNot Available
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP1.92ALOGPS
logP2.36ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)3.3ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area133.52 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity111.09 m³·mol⁻¹ChemAxon
Polarizability46.77 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-056r-8219500000-6befcfde02b865659c65Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0002-4222229000-9df02b5eaa81482e1d84Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-00kb-0150900000-dbbdbeaeaa0fb7b65b0cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-00kb-0150900000-78a9ec4beb4fe22a8735Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00fs-0190700000-ab622d54514a7c8dd7bbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0390000000-0ca06f8d5f8e2266eca1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fmi-0890000000-33ca823ccbdc77eec8b9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00kb-1252900000-1603a7df81c822d36aceSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-1291100000-aea6098c09be50c7aeb7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-3190000000-c37a96962dc8073839bcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-006t-0090800000-ac0903dfe69104eaa019Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01xt-0333900000-4ad5c8540eff279f8192Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0cg0-2934000000-4ee88a34dbe6cd0e8b57Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0000900000-dfac460c786c0c82c3beSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014j-6591800000-28870ff9517fe62979beSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0aor-7091200000-0d8562a190cdb0c97cc6Spectrum
Biological Properties
Cellular LocationsNot Available
Biofluid Locations and Tissue Locations
  • Urine
Concentrations
BiofluidStatusValueConditionSpeciesReferenceDetails
UrineDetected but not QuantifiedNot ApplicableNot AvailableBovine details
UrineDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
DrugBank IDNot Available
HMDB IDHMDB0004483
FooDB IDFDB021803
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG ID2304836
BioCyc IDESTRONE-SULFATE
METLIN ID7063
PDB IDE3G
Wikipedia LinkEstrone glucuronide
Chemspider ID103124
ChEBI ID28919
PubChem Compound ID115255
Kegg Compound IDC11133
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Eichner SF, Timpe EM: Urinary-based ovulation and pregnancy: point-of-care testing. Ann Pharmacother. 2004 Feb;38(2):325-31. Epub 2003 Dec 30. [14742773 ]
  2. Collins WP: The evolution of reference methods to monitor ovulation. Am J Obstet Gynecol. 1991 Dec;165(6 Pt 2):1994-6. [1755456 ]