(E)-3-(1-hydroxy-4-keto-cyclohexa-2,5-dien-1-yl)acrylic acid [(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(4-hydroxyphenoxy)tetrahydropyran-2-yl]methyl ester

A summary of the most common chemical descriptors (InChI Key and SMILES codes) for (E)-3-(1-hydroxy-4-keto-cyclohexa-2,5-dien-1-yl)acrylic acid [(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(4-hydroxyphenoxy)tetrahydropyran-2-yl]methyl ester are summarized together with 3D and 2D structures and relevant physico-chemical properties.

What is (E)-3-(1-hydroxy-4-keto-cyclohexa-2,5-dien-1-yl)acrylic acid [(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(4-hydroxyphenoxy)tetrahydropyran-2-yl]methyl ester?

The molecule (E)-3-(1-hydroxy-4-keto-cyclohexa-2,5-dien-1-yl)acrylic acid [(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(4-hydroxyphenoxy)tetrahydropyran-2-yl]methyl ester presents a molecular formula of C21H22O10 and its IUPAC name is [(2R,3S,4S,5R,6S)-3,4,5-tris(oxidanyl)-6-(4-oxidanylphenoxy)oxan-2-yl]methyl (E)-3-(1-oxidanyl-4-oxidanylidene-cyclohexa-2,5-dien-1-yl)prop-2-enoate.

3D structure

Cartesian coordinates

Geometry of (E)-3-(1-hydroxy-4-keto-cyclohexa-2,5-dien-1-yl)acrylic acid [(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(4-hydroxyphenoxy)tetrahydropyran-2-yl]methyl ester in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.

2D drawing

 

(E)-3-(1-hydroxy-4-keto-cyclohexa-2,5-dien-1-yl)acrylic acid [(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(4-hydroxyphenoxy)tetrahydropyran-2-yl]methyl ester KQIQKULTIAJZKL-VHFDLOJPSA-N chemical compound 2D structure molecule svg
(E)-3-(1-hydroxy-4-keto-cyclohexa-2,5-dien-1-yl)acrylic acid [(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(4-hydroxyphenoxy)tetrahydropyran-2-yl]methyl ester

 

Molecule descriptors

 
IUPAC name(E)-3-(1-hydroxy-4-keto-cyclohexa-2,5-dien-1-yl)acrylic acid [(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(4-hydroxyphenoxy)tetrahydropyran-2-yl]methyl ester
InChI codeInChI=1S/C21H22O10/c22-12-1-3-14(4-2-12)30-20-19(27)18(26)17(25)15(31-20)11-29-16(24)7-10-21(28)8-5-13(23)6-9-21/h1-10,15,17-20,22,25-28H,11H2/b10-7+/t15-,17-,18+,19-,20-/m1/s1
InChI KeyKQIQKULTIAJZKL-VHFDLOJPSA-N
SMILESC1=CC(=CC=C1O)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)COC(=O)/C=C/C3(C=CC(=O)C=C3)O)O)O)O

Physico-Chemical properties

IUPAC name[(2R,3S,4S,5R,6S)-3,4,5-tris(oxidanyl)-6-(4-oxidanylphenoxy)oxan-2-yl]methyl (E)-3-(1-oxidanyl-4-oxidanylidene-cyclohexa-2,5-dien-1-yl)prop-2-enoate
Molecular formulaC21H22O10
Molecular weight434.4
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity
LogP-0.6
Topological polar surface area163

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.