Showing metabocard for Estrone glucuronide (BMDB0004483)

IdentificationTaxonomyPhysical propertiesSpectraConcentrationsLinksReferencesXML
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Record Information
Version1.0
Creation Date2016-09-30 23:09:37 UTC
Update Date2020-06-04 18:59:03 UTC
MCDB ID BMDB0004483
Secondary Accession Numbers
  • BMDB04483
Metabolite Identification
Common NameEstrone glucuronide
DescriptionEstrone glucuronide 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. Thus, estrone glucuronide is considered to be a steroid conjugate lipid molecule. Estrone glucuronide exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. In cattle, estrone glucuronide is involved in the metabolic pathway called the estrone metabolism pathway.
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
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point254.5 °CNot 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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Concentrations
StatusValueReferenceDetails
Detected and Quantified0.00002 +/- 0.00001 uM details
Detected and Quantified0.0001 +/- 0.00002 uM details
Detected and Quantified0.00002 +/- 0.00001 uM details
Detected and Quantified0.00003 +/- 0.00002 uM details
Detected and Quantified0.00002 +/- 0.00002 uM details
Detected and Quantified0.00003 +/- 0.00001 uM details
HMDB IDHMDB0004483
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB021803
KNApSAcK IDNot Available
Chemspider ID103124
KEGG Compound IDC11133
BioCyc IDESTRONE-SULFATE
BiGG ID2304836
Wikipedia LinkEstrone glucuronide
METLIN ID7063
PubChem Compound115255
PDB IDE3G
ChEBI ID28919
References
Synthesis ReferenceWerschkun, Barbara; Gorziza, Karin; Thiem, Joachim. Synthesis of b-glucuronides of estradiol, ethynylestradiol and estrone. Journal of Carbohydrate Chemistry (1999), 18(6), 629-637.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Tso J, Aga DS: A systematic investigation to optimize simultaneous extraction and liquid chromatography tandem mass spectrometry analysis of estrogens and their conjugated metabolites in milk. J Chromatogr A. 2010 Jul 16;1217(29):4784-95. doi: 10.1016/j.chroma.2010.05.024. Epub 2010 May 25. [PubMed:20541211 ]