(2S)-2-methylbutyric acid [(3aS,4S,5S,6E,10Z,11aR)-5-acetoxy-2-keto-3-methylene-6,10-dimethylol-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-4-yl] ester

A summary of the most common chemical descriptors (InChI Key and SMILES codes) for (2S)-2-methylbutyric acid [(3aS,4S,5S,6E,10Z,11aR)-5-acetoxy-2-keto-3-methylene-6,10-dimethylol-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-4-yl] ester are summarized together with 3D and 2D structures and relevant physico-chemical properties.

What is (2S)-2-methylbutyric acid [(3aS,4S,5S,6E,10Z,11aR)-5-acetoxy-2-keto-3-methylene-6,10-dimethylol-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-4-yl] ester?

The molecule (2S)-2-methylbutyric acid [(3aS,4S,5S,6E,10Z,11aR)-5-acetoxy-2-keto-3-methylene-6,10-dimethylol-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-4-yl] ester presents a molecular formula of C22H30O8 and its IUPAC name is [(3aS,4S,5S,6E,10Z,11aR)-5-acetyloxy-6,10-bis(hydroxymethyl)-3-methylidene-2-oxidanylidene-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-4-yl] (2S)-2-methylbutanoate.

3D structure

Cartesian coordinates

Geometry of (2S)-2-methylbutyric acid [(3aS,4S,5S,6E,10Z,11aR)-5-acetoxy-2-keto-3-methylene-6,10-dimethylol-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-4-yl] ester in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.

2D drawing

 

(2S)-2-methylbutyric acid [(3aS,4S,5S,6E,10Z,11aR)-5-acetoxy-2-keto-3-methylene-6,10-dimethylol-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-4-yl] ester LQQVURUBFJKELJ-JADRZADDSA-N chemical compound 2D structure molecule svg
(2S)-2-methylbutyric acid [(3aS,4S,5S,6E,10Z,11aR)-5-acetoxy-2-keto-3-methylene-6,10-dimethylol-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-4-yl] ester

 

Molecule descriptors

 
IUPAC name(2S)-2-methylbutyric acid [(3aS,4S,5S,6E,10Z,11aR)-5-acetoxy-2-keto-3-methylene-6,10-dimethylol-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-4-yl] ester
InChI codeInChI=1S/C22H30O8/c1-5-12(2)21(26)30-20-18-13(3)22(27)29-17(18)9-15(10-23)7-6-8-16(11-24)19(20)28-14(4)25/h8-9,12,17-20,23-24H,3,5-7,10-11H2,1-2,4H3/b15-9-,16-8+/t12-,17+,18-,19-,20-/m0/s1
InChI KeyLQQVURUBFJKELJ-JADRZADDSA-N
SMILESCC[C@H](C)C(=O)O[C@H]1[C@@H]2[C@@H](/C=C(/CC/C=C(/[C@@H]1OC(=O)C)\CO)\CO)OC(=O)C2=C

Physico-Chemical properties

IUPAC name[(3aS,4S,5S,6E,10Z,11aR)-5-acetyloxy-6,10-bis(hydroxymethyl)-3-methylidene-2-oxidanylidene-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-4-yl] (2S)-2-methylbutanoate
Molecular formulaC22H30O8
Molecular weight422.5
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity
LogP0.8
Topological polar surface area119

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.