Showing metabocard for 17-beta-estradiol-3-glucuronide (BMDB0006224)

IdentificationTaxonomyPhysical propertiesSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 23:20:32 UTC
Update Date2020-06-04 18:59:38 UTC
MCDB ID BMDB0006224
Secondary Accession Numbers
  • BMDB06224
Metabolite Identification
Common Name17-beta-estradiol-3-glucuronide
Description17-beta-Estradiol-3-glucuronide, also known as estradiol-17-beta-3-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, 17-beta-estradiol-3-glucuronide is considered to be a steroid conjugate lipid molecule. 17-beta-Estradiol-3-glucuronide is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 17-beta-Estradiol-3-glucuronide and uridine 5'-diphosphate can be biosynthesized from estradiol and uridine diphosphate glucuronic acid; which is catalyzed by the enzyme UDP-glucuronosyltransferase 2B11. In cattle, 17-beta-estradiol-3-glucuronide is involved in the metabolic pathway called the androgen and estrogen metabolism pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
D-Myo-inositol 3,4-bisphosphateChEBI
Inositol 3,4-bisphosphateChEBI
D-Myo-inositol 3,4-bisphosphoric acidGenerator
Inositol 3,4-bisphosphoric acidGenerator
1D-Myo-inositol 3,4-bisphosphoric acidGenerator
1D-Myo-inositol 3,4-bis(dihydrogen phosphate)HMDB
Inositol 1,2-bisphosphateHMDB
Inositol 3,4-diphosphateHMDB
Myo-inositol 1,2-bisphosphateHMDB
17-b-Estradiol-3-glucuronideHMDB, Generator
17beta-Estradiol 3-(beta-D-glucuronide)HMDB
17beta-Estradiol 3-(beta-delta-glucuronide)HMDB
17beta-Estradiol 3-glucosiduronic acidHMDB
17beta-Estradiol 3-glucuronideHMDB
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
Estradiol-17beta 3-glucuronideHMDB
17-Β-estradiol-3-glucuronideGenerator
Chemical FormulaC24H32O8
Average Molecular Weight448.5061
Monoisotopic Molecular Weight448.209718
IUPAC Name(2S,3S,4S,5R)-3,4,5-trihydroxy-6-{[(1S,10R,11S,14S,15S)-14-hydroxy-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2(7),3,5-trien-5-yl]oxy}oxane-2-carboxylic acid
Traditional Name(2S,3S,4S,5R)-3,4,5-trihydroxy-6-{[(1S,10R,11S,14S,15S)-14-hydroxy-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2(7),3,5-trien-5-yl]oxy}oxane-2-carboxylic acid
CAS Registry NumberNot Available
SMILES
[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(OC1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O)C=C3
InChI Identifier
InChI=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-BFXFFQJBSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as inositol phosphates. Inositol phosphates are compounds containing a phosphate group attached to an inositol (or cyclohexanehexol) moiety.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassAlcohols and polyols
Direct ParentInositol phosphates
Alternative Parents
Substituents
  • Inositol phosphate
  • Monoalkyl phosphate
  • Cyclohexanol
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Secondary alcohol
  • Polyol
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
Polarizability47.13 ųChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-05o0-8117900000-bdd0040c22f30cb98ca62017-09-01View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0f6t-5301149000-d050a38838d064fd4fc32017-10-06View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-05aj-0190800000-0169a74c505ba35b8d522016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ab9-0190100000-ee17d0e62db863115f152016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ab9-1790000000-cfbd3a992d3d5f84b7462016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0fdk-1251900000-1ec925ccac5515788fc22016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fk9-1291200000-d4d7a6e72daa5a090ad52016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-3190000000-957b40de6016e046a6e92016-08-03View Spectrum
Concentrations
StatusValueReferenceDetails
Detected and Quantified0.0004 +/- 0.0001 uM details
Detected and Quantified0.0006 +/- 0.00001 uM details
Detected and Quantified0.0004 +/- 0.00003 uM details
Detected and Quantified0.00052 +/- 0.00003 uM details
Detected and Quantified0.0002 +/- 0.00001 uM details
Detected and Quantified0.0003 +/- 0.00002 uM details
HMDB IDHMDB0006235
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB023852
KNApSAcK IDNot Available
Chemspider ID389196
KEGG Compound IDC04063
BioCyc IDD-MYO-INOSITOL-34-BISPHOSPHATE
BiGG ID43066
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound440211
PDB IDNot Available
ChEBI ID28858
References
Synthesis ReferenceNot Available
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 ]