(+)-Stiripentol

A summary of the most common chemical descriptors (InChI Key and SMILES codes) for (+)-Stiripentol are summarized together with 3D and 2D structures and relevant physico-chemical properties.

What is the (+)-Stiripentol?

The molecule (+)-Stiripentol presents a molecular formula of C14H18O3 and its IUPAC name is (E,3R)-1-(1,3-benzodioxol-5-yl)-4,4-dimethylpent-1-en-3-ol.

Stiripentol is a molecule that has shown promise in the treatment of epilepsy. It is thought to work by modulating the activity of GABA, a neurotransmitter that participes in regulating the excitability of neurons. Stiripentol has been shown to increase the seizure threshold in animal models of epilepsy, and has also been shown to be effective in reducing seizure frequency in a small number of clinical trials in humans..

3D structure

Cartesian coordinates

Geometry of (+)-Stiripentol in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.

2D drawing

 

(+)-Stiripentol IBLNKMRFIPWSOY-VUDGCMKMSA-N chemical compound 2D structure molecule svg
(+)-Stiripentol

 

Molecule descriptors

 
IUPAC name(E,3R)-1-(1,3-benzodioxol-5-yl)-4,4-dimethylpent-1-en-3-ol
InChI codeInChI=1S/C14H18O3/c1-14(2,3)13(15)7-5-10-4-6-11-12(8-10)17-9-16-11/h4-8,13,15H,9H2,1-3H3/b7-5+/t13-/m1/s1
InChI KeyIBLNKMRFIPWSOY-VUDGCMKMSA-N
SMILESCC(C)(C)[C@H](O)/C=C/c1ccc2c(c1)OCO2

Other names (synonyms)

IUPAC nomenclature provides a standardized method for naming chemical compounds. Although this system is widely used in chemistry, many chemical compounds have also other names commonly used in different contexts. These synonyms can come from a variety of sources and are used for a variety of purposes.

One common source of synonyms for chemical compounds is the common or trivial names, assigned on the basis of appearance, properties, or origin of the molecule.

Another source of synonyms are historical or obsolete names employed in the past, however replaced nowadays by more modern or standardized names.

In addition to common and historical names, chemical compounds may also have synonyms that are specific to a particular field or industry.

  • (+)-Stiripentol
  • (+)-Stp
  • (E,3R)-1-(1,3-benzodioxol-5-yl)-4,4-dimethylpent-1-en-3-ol
  • (R)-(+)-Stiripentol
  • (R)-Stiripentol
  • 1-Penten-3-ol, 1-(1,3-benzodioxol-5-yl)-4,4-dimethyl-
  • 144017-65-2
  • 905E3Z0Z70
  • D-2232
  • J-007898
  • Q27271285
  • Stiripentol, (+)-

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC2005958
  • UNII-905E3Z0Z70
  • SCHEMBL10304813

Physico-Chemical properties

IUPAC name(E,3R)-1-(1,3-benzodioxol-5-yl)-4,4-dimethylpent-1-en-3-ol
Molecular formulaC14H18O3
Molecular weight234.291
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity67.53
LogP2.8
Topological polar surface area38.7

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.