4-Hydroxyestradiol

A summary of the most common chemical descriptors (InChI Key and SMILES codes) for 4-Hydroxyestradiol are summarized together with 3D and 2D structures and relevant physico-chemical properties.

What is the 4-Hydroxyestradiol?

The molecule 4-Hydroxyestradiol presents a molecular formula of C18H24O3 and its IUPAC name is (8R,9S,13S,14S,17S)-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-3,4,17-triol.

4-Hydroxyestradiol (4-OH-E2) is a natural metabolite of estradiol (E2) and is formed by the action of catechol-O-methyltransferase (COMT) on E2. 4-OH-E2 is a potent agonist of the estrogen receptor (ER) with an affinity for the ER that is similar to that of E2. However, 4-OH-E2 is less active than E2 in vivo, possibly due to its rapid metabolism. 4-OH-E2 has been shown to have both pro- and anti-tumorigenic effects in various animal models, depending on the dose and route of administration. 4-OH-E2 has also been shown to have neuroprotective effects in vitro and in vivo..

3D structure

Cartesian coordinates

Geometry of 4-Hydroxyestradiol in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.

2D drawing

 

4-Hydroxyestradiol QOZFCKXEVSGWGS-ZHIYBZGJSA-N chemical compound 2D structure molecule svg
4-Hydroxyestradiol

 

Molecule descriptors

 
IUPAC name(8R,9S,13S,14S,17S)-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-3,4,17-triol
InChI codeInChI=1S/C18H24O3/c1-18-9-8-11-10-4-6-15(19)17(21)13(10)3-2-12(11)14(18)5-7-16(18)20/h4,6,11-12,14,16,19-21H,2-3,5,7-9H2,1H3/t11-,12-,14+,16+,18+/m1/s1
InChI KeyQOZFCKXEVSGWGS-ZHIYBZGJSA-N
SMILESC[C@]12CC[C@@H]3c4ccc(O)c(O)c4CC[C@H]3[C@@H]1CC[C@@H]2O

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.

  • (17beta)-estra-1,3,5(10)-triene-3,4,17-triol
  • (1S,3aS,3bR,9bS,11aS)-11a-methyl-1H,2H,3H,3aH,3bH,4H,5H,9bH,10H,11H,11aH-cyclopenta[a]phenanthrene-1,6,7-triol
  • (8R,9S,13S,14S,17S)-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-3,4,17-triol
  • 1,3,5(10)-ESTRATRIENE-3,4,17.BETA.-TRIOL
  • 1,3,5[10]-ESTRATRIENE-3,4,17BETA-TRIOL
  • 3,4,17beta-estriol
  • 3,4,17beta-trihydroxy-1,3,5[10]-estratriene
  • 4,17 dihydroxy estradiol
  • 4-HYDROXYESTRADIOL
  • 4-Hydroxy-17-beta-estradiol
  • 4-Hydroxy-17?-estradiol
  • 4-Hydroxyestradiol
  • 4-Hydroxyestradiol-17beta
  • 4-OH-Estradiol
  • 4-hydroxy-17-estradiol
  • 4-hydroxy-17beta-estradiol
  • 4-hydroxy-estradiol
  • 4-hydroxyestradiol-17 beta
  • 4-hydroxylestradiol
  • 4OHE2
  • 5976-61-4
  • BDBM34649
  • BIDD:ER0171
  • C3ZO03450E
  • CCRIS 8710
  • ESTRA-1,3,5(10)-TRIENE-3,4,17-beta-TRIOL
  • ESTRADIOL METABOLITE (4-HYDROXYESTRADIOL)
  • Epitope ID:159259
  • Estra-1,3,5(10)-triene-3,4,17-triol, (17.beta.)-
  • Estra-1,3,5(10)-triene-3,4,17beta-triol
  • HMS2234M15
  • LMST02010028
  • MLS000069567
  • NCGC00247036-01
  • Opera_ID_1797
  • Q27104901
  • SMR000058747
  • cid_5282360
  • estra-1,3,5(10)-triene-2,4,17beta-triol
  • estra-1,3,5(10)-triene-3,14,17beta-triol

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC3814410
  • UNII-C3ZO03450E
  • DTXSID3022374
  • CHEMBL1412489
  • CHEBI:62845
  • SCHEMBL224398

Physico-Chemical properties

IUPAC name(8R,9S,13S,14S,17S)-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-3,4,17-triol
Molecular formulaC18H24O3
Molecular weight288.381
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity83.05
LogP3.3
Topological polar surface area60.7

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.