3,4,5-trimethoxybenzoic acid [(2S)-2-(dimethylamino)-2-phenyl-butyl] ester

A summary of the most common chemical descriptors (InChI Key and SMILES codes) for 3,4,5-trimethoxybenzoic acid [(2S)-2-(dimethylamino)-2-phenyl-butyl] ester are summarized together with 3D and 2D structures and relevant physico-chemical properties.

What is 3,4,5-trimethoxybenzoic acid [(2S)-2-(dimethylamino)-2-phenyl-butyl] ester?

The molecule 3,4,5-trimethoxybenzoic acid [(2S)-2-(dimethylamino)-2-phenyl-butyl] ester presents a molecular formula of C22H29NO5 and its IUPAC name is [(2S)-2-(dimethylamino)-2-phenyl-butyl] 3,4,5-trimethoxybenzoate.

3D structure

Cartesian coordinates

Geometry of 3,4,5-trimethoxybenzoic acid [(2S)-2-(dimethylamino)-2-phenyl-butyl] ester in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.

2D drawing

 

3,4,5-trimethoxybenzoic acid [(2S)-2-(dimethylamino)-2-phenyl-butyl] ester LORDFXWUHHSAQU-JOCHJYFZSA-N chemical compound 2D structure molecule svg
3,4,5-trimethoxybenzoic acid [(2S)-2-(dimethylamino)-2-phenyl-butyl] ester

 

Molecule descriptors

 
IUPAC name3,4,5-trimethoxybenzoic acid [(2S)-2-(dimethylamino)-2-phenyl-butyl] ester
InChI codeInChI=1S/C22H29NO5/c1-7-22(23(2)3,17-11-9-8-10-12-17)15-28-21(24)16-13-18(25-4)20(27-6)19(14-16)26-5/h8-14H,7,15H2,1-6H3/t22-/m1/s1
InChI KeyLORDFXWUHHSAQU-JOCHJYFZSA-N
SMILESCC[C@@](COC(=O)C1=CC(=C(C(=C1)OC)OC)OC)(C2=CC=CC=C2)N(C)C

Physico-Chemical properties

IUPAC name[(2S)-2-(dimethylamino)-2-phenyl-butyl] 3,4,5-trimethoxybenzoate
Molecular formulaC22H29NO5
Molecular weight387.5
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity
LogP4
Topological polar surface area57.2

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.