N-[(1S)-2-amino-1-(1H-imidazol-5-ylmethyl)-2-keto-ethyl]carbamic acid benzyl ester

A summary of the most common chemical descriptors (InChI Key and SMILES codes) for N-[(1S)-2-amino-1-(1H-imidazol-5-ylmethyl)-2-keto-ethyl]carbamic acid benzyl ester are summarized together with 3D and 2D structures and relevant physico-chemical properties.

What is N-[(1S)-2-amino-1-(1H-imidazol-5-ylmethyl)-2-keto-ethyl]carbamic acid benzyl ester?

The molecule N-[(1S)-2-amino-1-(1H-imidazol-5-ylmethyl)-2-keto-ethyl]carbamic acid benzyl ester presents a molecular formula of C14H16N4O3 and its IUPAC name is (phenylmethyl) N-[(2S)-1-azanyl-3-(1H-imidazol-5-yl)-1-oxidanylidene-propan-2-yl]carbamate.

3D structure

Cartesian coordinates

Geometry of N-[(1S)-2-amino-1-(1H-imidazol-5-ylmethyl)-2-keto-ethyl]carbamic acid benzyl ester in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.

2D drawing

 

N-[(1S)-2-amino-1-(1H-imidazol-5-ylmethyl)-2-keto-ethyl]carbamic acid benzyl ester YLVGCKUYWFCKIV-LBPRGKRZSA-N chemical compound 2D structure molecule svg
N-[(1S)-2-amino-1-(1H-imidazol-5-ylmethyl)-2-keto-ethyl]carbamic acid benzyl ester

 

Molecule descriptors

 
IUPAC nameN-[(1S)-2-amino-1-(1H-imidazol-5-ylmethyl)-2-keto-ethyl]carbamic acid benzyl ester
InChI codeInChI=1S/C14H16N4O3/c15-13(19)12(6-11-7-16-9-17-11)18-14(20)21-8-10-4-2-1-3-5-10/h1-5,7,9,12H,6,8H2,(H2,15,19)(H,16,17)(H,18,20)/t12-/m0/s1
InChI KeyYLVGCKUYWFCKIV-LBPRGKRZSA-N
SMILESC1=CC=C(C=C1)COC(=O)N[C@@H](CC2=CN=CN2)C(=O)N

Physico-Chemical properties

IUPAC name(phenylmethyl) N-[(2S)-1-azanyl-3-(1H-imidazol-5-yl)-1-oxidanylidene-propan-2-yl]carbamate
Molecular formulaC14H16N4O3
Molecular weight288.30
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity
LogP0.5
Topological polar surface area110

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.