(+)-Thalidomide

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

What is the (+)-Thalidomide?

The molecule (+)-Thalidomide presents a molecular formula of C13H10N2O4 and its IUPAC name is 2-[(3R)-2,6-dioxopiperidin-3-yl]isoindole-1,3-dione.

(+)-Thalidomide is a molecule with a unique structure that allows it to bind to and inhibit the activity of a number of different proteins. Its therapeutic use is primarily in the treatment of leprosy and multiple myeloma, although it is also being investigated for use in a number of other conditions..

The structure of thalidomide is a central carbon atom with four nitrogen atoms and two oxygen atoms attached. The nitrogen atoms are arranged in a ring structure, and the oxygen atoms are located at the ends of the molecule. The unique structure of thalidomide allows it to bind to a number of different proteins, including tumor necrosis factor (TNF), interleukin-6 (IL-6), and transforming growth factor-beta (TGF-β)..

The binding of thalidomide to these proteins results in the inhibition of their activity, which leads to the therapeutic effects of thalidomide. In leprosy, thalidomide inhibits the activity of TNF, which leads to the reduction of inflammation and the destruction of the mycobacteria that cause the disease. In multiple myeloma, thalidomide inhibits the activity of IL-6, which leads to the reduction of tumor growth and the destruction of the cancer cells..

Although thalidomide is primarily used to treat leprosy and multiple myeloma, it is also being investigated for use in a number of other conditions, including Crohn's disease, psoriasis, and lupus. The unique structure of thalidomide makes it a promising therapeutic agent for a variety of conditions..

3D structure

Cartesian coordinates

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

2D drawing

 

(+)-Thalidomide UEJJHQNACJXSKW-SECBINFHSA-N chemical compound 2D structure molecule svg
(+)-Thalidomide

 

Molecule descriptors

 
IUPAC name2-[(3R)-2,6-dioxopiperidin-3-yl]isoindole-1,3-dione
InChI codeInChI=1S/C13H10N2O4/c16-10-6-5-9(11(17)14-10)15-12(18)7-3-1-2-4-8(7)13(15)19/h1-4,9H,5-6H2,(H,14,16,17)/t9-/m1/s1
InChI KeyUEJJHQNACJXSKW-SECBINFHSA-N
SMILESO=C1CC[C@@H](N2C(=O)c3ccccc3C2=O)C(=O)N1

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.

  • (+)-(R)-THALIDOMIDE
  • (+)-Thalidomide
  • (R)-(+)-thalidomide
  • (R)-(D)-Thalidomide
  • (R)-2-(2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione
  • (R)-Thalidomide
  • 1H-ISOINDOLE-1,3(2H)-DIONE, 2-((3R)-2,6-DIOXO-3-PIPERIDINYL)-
  • 1H-Isoindole-1,3(2H)-dione, 2-(2,6-dioxo-3-piperidinyl)-, (R)-
  • 2-((3R)-2,6-DIOXO-3-PIPERIDINYL)-1H-ISOINDOLE-1,3(2H)-DIONE
  • 2-[(3R)-2,6-dioxopiperidin-3-yl]-1H-isoindole-1,3(2H)-dione
  • 2-[(3R)-2,6-dioxopiperidin-3-yl]-2,3-dihydro-1H-isoindole-1,3-dione
  • 2-[(3R)-2,6-dioxopiperidin-3-yl]isoindole-1,3-dione
  • 2-[(3~{R})-2,6-bis(oxidanylidene)piperidin-3-yl]isoindole-1,3-dione
  • 2614-06-4
  • 6EL
  • BDBM65362
  • BIDD:ER0498
  • CCG-36381
  • CS-0021929
  • D-Thalidomide
  • HY-14658B
  • J-016277
  • N-(I+/--Glutarimidyl)phthalimide
  • N-(alpha-Glutarimido)-phthalimide
  • NSC 91729
  • NSC-91729
  • Phthalimide, N-(2,6-dioxo-3-piperidyl)-, (+)-
  • Phthalimide, N-(2,6-dioxo-3-piperidyl)-, D-(+)-
  • Q27131492
  • QN61H68KLK
  • R-(+)-Thalidomide
  • R-(D)-THALIDOMIDE
  • R-Thalidomide
  • Thalidomide, (R)-
  • rac-2-(2,6-Dioxo-3-piperidinyl)-1H-isoindole-1,3(2H)-dione

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC1530948
  • UNII-QN61H68KLK
  • DTXSID6046971
  • CHEMBL558551
  • CHEBI:61917
  • SCHEMBL41641

Physico-Chemical properties

IUPAC name2-[(3R)-2,6-dioxopiperidin-3-yl]isoindole-1,3-dione
Molecular formulaC13H10N2O4
Molecular weight258.23
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity70.95
LogP0.4
Topological polar surface area83.6

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.