(2S)-2-amino-3-methyl-butyric acid benzyl ester

A summary of the most common chemical descriptors (InChI Key and SMILES codes) for (2S)-2-amino-3-methyl-butyric acid benzyl ester are summarized together with 3D and 2D structures and relevant physico-chemical properties.

What is (2S)-2-amino-3-methyl-butyric acid benzyl ester?

The molecule (2S)-2-amino-3-methyl-butyric acid benzyl ester presents a molecular formula of C12H17NO2 and its IUPAC name is (phenylmethyl) (2S)-2-azanyl-3-methyl-butanoate.

3D structure

Cartesian coordinates

Geometry of (2S)-2-amino-3-methyl-butyric acid benzyl ester in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.

2D drawing

 

(2S)-2-amino-3-methyl-butyric acid benzyl ester YIRBOOICRQFSOK-NSHDSACASA-N chemical compound 2D structure molecule svg
(2S)-2-amino-3-methyl-butyric acid benzyl ester

 

Molecule descriptors

 
IUPAC name(2S)-2-amino-3-methyl-butyric acid benzyl ester
InChI codeInChI=1S/C12H17NO2/c1-9(2)11(13)12(14)15-8-10-6-4-3-5-7-10/h3-7,9,11H,8,13H2,1-2H3/t11-/m0/s1
InChI KeyYIRBOOICRQFSOK-NSHDSACASA-N
SMILESCC(C)[C@@H](C(=O)OCC1=CC=CC=C1)N

Physico-Chemical properties

IUPAC name(phenylmethyl) (2S)-2-azanyl-3-methyl-butanoate
Molecular formulaC12H17NO2
Molecular weight207.27
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity
LogP
Topological polar surface area52.3

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.