2-bromobenzoic acid [(2Z)-3-keto-2-(4-pyridylmethylene)coumaran-6-yl] ester

A summary of the most common chemical descriptors (InChI Key and SMILES codes) for 2-bromobenzoic acid [(2Z)-3-keto-2-(4-pyridylmethylene)coumaran-6-yl] ester are summarized together with 3D and 2D structures and relevant physico-chemical properties.

What is 2-bromobenzoic acid [(2Z)-3-keto-2-(4-pyridylmethylene)coumaran-6-yl] ester?

The molecule 2-bromobenzoic acid [(2Z)-3-keto-2-(4-pyridylmethylene)coumaran-6-yl] ester presents a molecular formula of C21H12BrNO4 and its IUPAC name is [(2Z)-3-oxidanylidene-2-(pyridin-4-ylmethylidene)-1-benzofuran-6-yl] 2-bromanylbenzoate.

3D structure

Cartesian coordinates

Geometry of 2-bromobenzoic acid [(2Z)-3-keto-2-(4-pyridylmethylene)coumaran-6-yl] ester in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.

2D drawing

 

2-bromobenzoic acid [(2Z)-3-keto-2-(4-pyridylmethylene)coumaran-6-yl] ester LNZTYYIIMUGYRU-ODLFYWEKSA-N chemical compound 2D structure molecule svg
2-bromobenzoic acid [(2Z)-3-keto-2-(4-pyridylmethylene)coumaran-6-yl] ester

 

Molecule descriptors

 
IUPAC name2-bromobenzoic acid [(2Z)-3-keto-2-(4-pyridylmethylene)coumaran-6-yl] ester
InChI codeInChI=1S/C21H12BrNO4/c22-17-4-2-1-3-15(17)21(25)26-14-5-6-16-18(12-14)27-19(20(16)24)11-13-7-9-23-10-8-13/h1-12H/b19-11-
InChI KeyLNZTYYIIMUGYRU-ODLFYWEKSA-N
SMILESC1=CC=C(C(=C1)C(=O)OC2=CC3=C(C=C2)C(=O)/C(=C/C4=CC=NC=C4)/O3)Br

Physico-Chemical properties

IUPAC name[(2Z)-3-oxidanylidene-2-(pyridin-4-ylmethylidene)-1-benzofuran-6-yl] 2-bromanylbenzoate
Molecular formulaC21H12BrNO4
Molecular weight422.2
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity
LogP4.6
Topological polar surface area65.5

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.