(1R,2R,3S,4S)-2-(3,4-dimethoxyphenyl)-4-hydroxy-6-keto-4-methyl-cyclohexane-1,3-dicarboxylic acid diisobutyl ester

A summary of the most common chemical descriptors (InChI Key and SMILES codes) for (1R,2R,3S,4S)-2-(3,4-dimethoxyphenyl)-4-hydroxy-6-keto-4-methyl-cyclohexane-1,3-dicarboxylic acid diisobutyl ester are summarized together with 3D and 2D structures and relevant physico-chemical properties.

What is (1R,2R,3S,4S)-2-(3,4-dimethoxyphenyl)-4-hydroxy-6-keto-4-methyl-cyclohexane-1,3-dicarboxylic acid diisobutyl ester?

The molecule (1R,2R,3S,4S)-2-(3,4-dimethoxyphenyl)-4-hydroxy-6-keto-4-methyl-cyclohexane-1,3-dicarboxylic acid diisobutyl ester presents a molecular formula of C25H36O8 and its IUPAC name is bis(2-methylpropyl) (1R,2R,3S,4S)-2-(3,4-dimethoxyphenyl)-4-methyl-4-oxidanyl-6-oxidanylidene-cyclohexane-1,3-dicarboxylate.

3D structure

Cartesian coordinates

Geometry of (1R,2R,3S,4S)-2-(3,4-dimethoxyphenyl)-4-hydroxy-6-keto-4-methyl-cyclohexane-1,3-dicarboxylic acid diisobutyl ester in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.

2D drawing

 

(1R,2R,3S,4S)-2-(3,4-dimethoxyphenyl)-4-hydroxy-6-keto-4-methyl-cyclohexane-1,3-dicarboxylic acid diisobutyl ester NCTYGLPITBDCSR-FUCAVZNHSA-N chemical compound 2D structure molecule svg
(1R,2R,3S,4S)-2-(3,4-dimethoxyphenyl)-4-hydroxy-6-keto-4-methyl-cyclohexane-1,3-dicarboxylic acid diisobutyl ester

 

Molecule descriptors

 
IUPAC name(1R,2R,3S,4S)-2-(3,4-dimethoxyphenyl)-4-hydroxy-6-keto-4-methyl-cyclohexane-1,3-dicarboxylic acid diisobutyl ester
InChI codeInChI=1S/C25H36O8/c1-14(2)12-32-23(27)21-17(26)11-25(5,29)22(24(28)33-13-15(3)4)20(21)16-8-9-18(30-6)19(10-16)31-7/h8-10,14-15,20-22,29H,11-13H2,1-7H3/t20-,21-,22+,25-/m0/s1
InChI KeyNCTYGLPITBDCSR-FUCAVZNHSA-N
SMILESCC(C)COC(=O)[C@@H]1[C@@H]([C@@H]([C@@](CC1=O)(C)O)C(=O)OCC(C)C)C2=CC(=C(C=C2)OC)OC

Physico-Chemical properties

IUPAC namebis(2-methylpropyl) (1R,2R,3S,4S)-2-(3,4-dimethoxyphenyl)-4-methyl-4-oxidanyl-6-oxidanylidene-cyclohexane-1,3-dicarboxylate
Molecular formulaC25H36O8
Molecular weight464.5
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity
LogP4.1
Topological polar surface area108

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.