Estradiol-17beta-glucuronide

A summary of the most common chemical descriptors (InChI Key and SMILES codes) for Estradiol-17beta-glucuronide are summarized together with 3D and 2D structures and relevant physico-chemical properties.

What is the Estradiol-17beta-glucuronide?

The molecule Estradiol-17beta-glucuronide presents a molecular formula of C24H32O8 and its IUPAC name is (2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-[[(8R,9S,13S,14S,17S)-3-hydroxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl]oxy]oxane-2-carboxylic acid.

Estradiol-17beta-glucuronide (E2-17beta-G) is a molecule that is produced by the body as a breakdown product of estradiol, an important female sex hormone. E2-17beta-G is also present in birth control pills and other hormone therapies..

E2-17beta-G is thought to be less active than estradiol itself, but its exact role in the body is not well understood. Some research suggests that it may play a role in the development of certain types of cancer, but this is not yet proven..

E2-17beta-G is not approved by the FDA for any specific medical use, but it is sometimes used as a “marker” to measure estradiol levels in the body..

More research is needed to understand the potential risks and benefits of E2-17beta-G..

3D structure

Cartesian coordinates

Geometry of Estradiol-17beta-glucuronide in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.

2D drawing

 

Estradiol-17beta-glucuronide MTKNDAQYHASLID-QXYWQCSFSA-N chemical compound 2D structure molecule svg
Estradiol-17beta-glucuronide

 

Molecule descriptors

 
IUPAC name(2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-[[(8R,9S,13S,14S,17S)-3-hydroxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl]oxy]oxane-2-carboxylic acid
InChI codeInChI=1S/C24H32O8/c1-24-9-8-14-13-5-3-12(25)10-11(13)2-4-15(14)16(24)6-7-17(24)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 KeyMTKNDAQYHASLID-QXYWQCSFSA-N
SMILESC[C@]12CC[C@@H]3c4ccc(O)cc4CC[C@H]3[C@@H]1CC[C@@H]2O[C@@H]1O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]1O

Other names (synonyms)

IUPAC nomenclature provides a standardized method for naming chemical compounds. Although this system is widely used in chemistry, many chemical compounds have also other names commonly used in different contexts. These synonyms can come from a variety of sources and are used for a variety of purposes.

One common source of synonyms for chemical compounds is the common or trivial names, assigned on the basis of appearance, properties, or origin of the molecule.

Another source of synonyms are historical or obsolete names employed in the past, however replaced nowadays by more modern or standardized names.

In addition to common and historical names, chemical compounds may also have synonyms that are specific to a particular field or industry.

  • (2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-[[(8R,9S,13S,14S,17S)-3-hydroxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl]oxy]oxane-2-carboxylic acid
  • (2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-{[(1S,10R,11S,14S,15S)-5-hydroxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-trien-14-yl]oxy}oxane-2-carboxylic acid
  • .beta.-D-Glucopyranosiduronic acid, (17?)-3-hydroxyestra-1,3,5(10)-trien-17-yl
  • 17-Beta-Estradiol (3 Glucuronidation)
  • 17beta-Estradiol 17-(beta-D-glucuronide)
  • 17beta-Estradiol 17beta-D-glucuronide
  • 17beta-estradiol 17-glucosiduronic acid
  • 17beta-estradiol-17-(beta-D-glucuronide)
  • 1806-98-0
  • 3-hydroxyestra-1,3,5(10)-trien-17beta-yl beta-D-glucopyranosiduronic acid
  • BDBM50344959
  • Estradiol 17beta-glucuronide
  • Estradiol-17B-Glucuronide
  • Estradiol-17beta-glucuronide
  • GTPL4687
  • Glucuronosylestradiol
  • LMST05010025
  • Oestradiol-17beta-glucuronide
  • Q26998368
  • [3H]-estradiol-17beta-glucuronide
  • [3H]estradiol-17beta-glucuronide
  • beta-D-Glucopyranosiduronic acid, (17beta)-3-hydroxyestra-1,3,5(10)-trien-17-yl
  • estra-1,3,5(10)-triene-3,17beta-diol 17-D-glucuronoside
  • estradiol 17b glucuronide

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC4099035
  • DTXSID50862756
  • CHEMBL1697724
  • CHEBI:791
  • SCHEMBL57240

Physico-Chemical properties

IUPAC name(2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-[[(8R,9S,13S,14S,17S)-3-hydroxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl]oxy]oxane-2-carboxylic acid
Molecular formulaC24H32O8
Molecular weight448.506
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity114.02
LogP1.5
Topological polar surface area136.7

LogP and topological polar surface area (TPSA) values were estimated using Open Babel software.

The n-octanol/water partition coeficient (Kow) data is applied in toxicology and drug research. Kow values are used, to guess the environmental fate of persistent organic pollutants. High partition coefficients values, tend to accumulate in the fatty tissue of organisms. Molecules with a log(Kow) (or LogP) greater than 5 are considered to bioaccumulate.

TPSA values are the sum of the surface area over all polar atoms or molecules, mainly oxygen and nitrogen, also including hydrogen atoms.

In medicinal chemistry, TPSA is used to assess the ability of a drug to permeabilise cells.

For molecules to penetrate the blood-brain barrier (and act on receptors in the central nervous system), TPSA values below 90 Å2 are required. Thus, molecules with a polar surface area greater than 140 Å2 tend to be poorly permeable to cell membranes.