Isodienestrol

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

What is the Isodienestrol?

The molecule Isodienestrol presents a molecular formula of C18H18O2 and its IUPAC name is 4-[(2Z,4Z)-4-(4-hydroxyphenyl)hexa-2,4-dien-3-yl]phenol.

Isodienestrol is a molecule that was first synthesized in 1936. It is a synthetic estrogen and was used in the treatment of menopausal symptoms and uterine bleeding. It was also used in birth control pills. However, it was taken off the market in the 1970s due to concerns about its safety..

3D structure

Cartesian coordinates

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

2D drawing

 

Isodienestrol NFDFQCUYFHCNBW-XBMAZEBWSA-N chemical compound 2D structure molecule svg
Isodienestrol

 

Molecule descriptors

 
IUPAC name4-[(2Z,4Z)-4-(4-hydroxyphenyl)hexa-2,4-dien-3-yl]phenol
InChI codeInChI=1S/C18H18O2/c1-3-17(13-5-9-15(19)10-6-13)18(4-2)14-7-11-16(20)12-8-14/h3-12,19-20H,1-2H3/b17-3-,18-4-
InChI KeyNFDFQCUYFHCNBW-XBMAZEBWSA-N
SMILESC/C=C(C(=C/C)\c1ccc(O)cc1)/c1ccc(O)cc1

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.

  • (Z,Z)-Dienestrol
  • .BETA.-DIENESTROL
  • 35495-11-5
  • 4-[(2Z,4Z)-4-(4-hydroxyphenyl)hexa-2,4-dien-3-yl]phenol
  • 45CG6C2N6E
  • CCRIS 7090
  • CIS,CIS-DIENESTROL
  • DIENESTROL, .BETA.-
  • Isodienestrol
  • Phenol, 4,4'-((1Z,2Z)-1,2-diethylidene-1,2-ethanediyl)bis-
  • Phenol, 4,4'-(1,2-diethylidene-1,2-ethanediyl)bis-, (Z,Z)-
  • Q27258829
  • Z,Z-DIES
  • Z,Z-Dienestrol
  • beta-Dienestrol

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC4742540
  • UNII-45CG6C2N6E
  • AKOS024355670
  • DTXSID40859130
  • CHEMBL72364
  • SCHEMBL2896848

Physico-Chemical properties

IUPAC name4-[(2Z,4Z)-4-(4-hydroxyphenyl)hexa-2,4-dien-3-yl]phenol
Molecular formulaC18H18O2
Molecular weight266.334
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity84.61
LogP4.6
Topological polar surface area40.5

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.