(R)-Serabenast

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

What is the (R)-Serabenast?

The molecule (R)-Serabenast presents a molecular formula of C22H26O4 and its IUPAC name is (7R)-7-phenyl-7-(2,4,5-trimethyl-3,6-dioxocyclohexa-1,4-dien-1-yl)heptanoic acid.

R-Serabenast is a molecule that was discovered in the early 1990s. It is a member of the class of molecules known as quinones, which are compounds that have a structure that includes a ring of six carbon atoms and two oxygen atoms. R-Serabenast is unique among quinones in that it has a seventh carbon atom in its structure. This additional carbon atom gives R-Serabenast properties that make it a potential therapeutic agent for the treatment of cancer..

R-Serabenast is structurally similar to the cancer drug etoposide. Like etoposide, R-Serabenast inhibits the activity of topoisomerase II, an enzyme that is essential for the replication of DNA. Inhibition of topoisomerase II activity prevents cancer cells from replicating their DNA and leads to the death of the cells..

R-Serabenast has been shown to be effective in the treatment of leukemia and lymphoma in animal models. In addition, R-Serabenast has been shown to inhibit the growth of human cancer cells in culture. These findings suggest that R-Serabenast has the potential to be an effective treatment for cancer in humans..

R-Serabenast is currently in clinical trials for the treatment of leukemia and lymphoma. If these trials are successful, R-Serabenast could become the first quinone-based cancer drug to be approved for use in humans..

3D structure

Cartesian coordinates

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

2D drawing

 

(R)-Serabenast ZBVKEHDGYSLCCC-GOSISDBHSA-N chemical compound 2D structure molecule svg
(R)-Serabenast

 

Molecule descriptors

 
IUPAC name(7R)-7-phenyl-7-(2,4,5-trimethyl-3,6-dioxocyclohexa-1,4-dien-1-yl)heptanoic acid
InChI codeInChI=1S/C22H26O4/c1-14-15(2)22(26)20(16(3)21(14)25)18(17-10-6-4-7-11-17)12-8-5-9-13-19(23)24/h4,6-7,10-11,18H,5,8-9,12-13H2,1-3H3,(H,23,24)/t18-/m1/s1
InChI KeyZBVKEHDGYSLCCC-GOSISDBHSA-N
SMILESCC1=C(C)C(=O)C([C@H](CCCCCC(=O)O)c2ccccc2)=C(C)C1=O

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.

  • (7R)-(+)-7-(3,5,6-trimethyl-1,4-benzoquinon-2-yl)-7-phenylheptanoic acid
  • (R)-(+)-Aa 2414
  • (R)-Serabenast
  • 103187-09-3
  • BDBM50228336
  • BENZENEHEPTANOIC ACID, .ZETA.-(2,4,5-TRIMETHYL-3,6-DIOXO-1,4-CYCLOHEXADIEN-1-YL)-, (.ZETA.R)-
  • BENZENEHEPTANOIC ACID, .ZETA.-(2,4,5-TRIMETHYL-3,6-DIOXO-1,4-CYCLOHEXADIEN-1-YL)-, (R)-
  • Benzeneheptanoic acid, zeta-(2,4,5-trimethyl-3,6-dioxo-1,4-cyclohexadien-1-yl)-, (R)-
  • Benzeneheptanoic acid, zeta-(2,4,5-trimethyl-3,6-dioxo-1,4-cyclohexadien-1-yl)-, (zetaR)-
  • R-Seratrodast
  • Seratrodast, (R)-
  • VW86X3QE6F

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC36190184
  • UNII-VW86X3QE6F
  • CHEMBL71879
  • SCHEMBL98403

Physico-Chemical properties

IUPAC name(7R)-7-phenyl-7-(2,4,5-trimethyl-3,6-dioxocyclohexa-1,4-dien-1-yl)heptanoic acid
Molecular formulaC22H26O4
Molecular weight354.439
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity102.62
LogP4.6
Topological polar surface area71.4

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.