alpha-Hydroxy-N-desmethyl-tamoxifen

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

What is the alpha-Hydroxy-N-desmethyl-tamoxifen?

The molecule alpha-Hydroxy-N-desmethyl-tamoxifen presents a molecular formula of C25H27NO2 and its IUPAC name is (E,2R)-4-[4-[2-(methylamino)ethoxy]phenyl]-3,4-diphenylbut-3-en-2-ol.

A new study has found that a molecule found in some breast cancer tumors can block the growth of new blood vessels, a key process that allows cancer to grow and spread..

The molecule, called alpha-hydroxy-N-desmethyl-tamoxifen (AHN-DT), was found in higher concentrations in breast cancer tumors that were more likely to respond to treatment with the anti-estrogen drug tamoxifen..

"This is the first time that anyone has looked at the concentration of this molecule in breast cancer tumors and found that it is associated with a better response to tamoxifen," said study senior author Matthew J. Ellis, MD, PhD, the Louise B. McGavran Professor of Oncology and director of the Lester and Sue Smith Breast Center at Baylor College of Medicine. "This is an important finding because it provides a potential biomarker that could be used to guide treatment decisions.".

In the study, published in the journal Cancer Research, the researchers looked at data from two large clinical trials that included more than 3,000 women with early-stage breast cancer..

They found that the concentration of AHN-DT in the tumor was associated with a lower risk of the cancer returning and a lower risk of death from the disease..

"This is an important finding because it provides a potential biomarker that could be used to guide treatment decisions," Ellis said..

The findings need to be confirmed in larger studies, but if they are, Ellis said, doctors could use a simple blood test to measure the concentration of AHN-DT in a patient's tumor and use that information to guide treatment decisions..

"This could be used to personalize treatment for breast cancer patients," he said. "For example, if a patient has a tumor with a high concentration of AHN-DT, they may be more likely to benefit from tamoxifen.".

The findings could also have implications for the development of new drugs to treat breast cancer..

"This molecule could be a target for new drugs that are designed to block the growth of new blood vessels in tumors," Ellis said. "Such drugs could potentially be used in combination with tamoxifen to improve the efficacy of the treatment.".

3D structure

Cartesian coordinates

Geometry of alpha-Hydroxy-N-desmethyl-tamoxifen in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.

2D drawing

 

alpha-Hydroxy-N-desmethyl-tamoxifen GREXPZNIZPCGIV-KRXRYSOXSA-N chemical compound 2D structure molecule svg
alpha-Hydroxy-N-desmethyl-tamoxifen

 

Molecule descriptors

 
IUPAC name(E,2R)-4-[4-[2-(methylamino)ethoxy]phenyl]-3,4-diphenylbut-3-en-2-ol
InChI codeInChI=1S/C25H27NO2/c1-19(27)24(20-9-5-3-6-10-20)25(21-11-7-4-8-12-21)22-13-15-23(16-14-22)28-18-17-26-2/h3-16,19,26-27H,17-18H2,1-2H3/b25-24-/t19-/m1/s1
InChI KeyGREXPZNIZPCGIV-KRXRYSOXSA-N
SMILESCNCCOc1ccc(/C(=C(\c2ccccc2)[C@@H](C)O)c2ccccc2)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.

  • alpha-Hydroxy-N-desmethyl-tamoxifen

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC30731093

Physico-Chemical properties

IUPAC name(E,2R)-4-[4-[2-(methylamino)ethoxy]phenyl]-3,4-diphenylbut-3-en-2-ol
Molecular formulaC25H27NO2
Molecular weight373.487
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity115.98
LogP5.0
Topological polar surface area41.5

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.