Thioinosine

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

What is the Thioinosine?

The molecule Thioinosine presents a molecular formula of C10H12N4O4S and its IUPAC name is 9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-3H-purine-6-thione.

Thioinosine is a nucleoside composed of thiopurine and inosine. It belongs in the thiopurine nucleoside analogue family of drugs. Thioinosine is an antineoplastic agent used in the treatment of leukemia. It is also being investigated for the treatment of other cancers..

3D structure

Cartesian coordinates

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

2D drawing

 

Thioinosine NKGPJODWTZCHGF-KQYNXXCUSA-N chemical compound 2D structure molecule svg
Thioinosine

 

Molecule descriptors

 
IUPAC name9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-3H-purine-6-thione
InChI codeInChI=1S/C10H12N4O4S/c15-1-4-6(16)7(17)10(18-4)14-3-13-5-8(14)11-2-12-9(5)19/h2-4,6-7,10,15-17H,1H2,(H,11,12,19)/t4-,6-,7-,10-/m1/s1
InChI KeyNKGPJODWTZCHGF-KQYNXXCUSA-N
SMILESOC[C@H]1O[C@@H](n2cnc3c(=S)[nH]cnc32)[C@H](O)[C@@H]1O

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.

  • (2R,3S,4R,5R)-2-(Hydroxymethyl)-5-(6-mercapto-9H-purin-9-yl)tetrahydrofuran-3,4-diol
  • (2R,3S,4R,5R)-2-(hydroxymethyl)-5-(6-sulfanyl-9H-purin-9-yl)oxolane-3,4-diol
  • 46S541971T
  • 4988-64-1
  • 574-25-4
  • 6-MP-Riboside
  • 6-MPR
  • 6-Mercapto-9beta-D-ribofuranosyl-9H-purine
  • 6-Mercaptoinosine
  • 6-Mercaptopurine 9beta-D-ribofuranoside
  • 6-Mercaptopurine ribonucleoside
  • 6-Mercaptopurine riboside (JAN)
  • 6-Mercaptopurine-9-
  • 6-Mercaptopurine-9-D-riboside
  • 6-Mercaptopurine-9-beta-D-ribofuranoside
  • 6-Thioinosine
  • 6-Thiopurine ribonucleoside
  • 6-mercaptopurine riboside
  • 6-mercaptopurine-riboside
  • 6H-Purine-6-thione, 1,9-dihydro-9-beta-D-ribofuranosyl-
  • 6H-Purine-6-thione, 1,9-dihydro-9-ribofuranosyl-
  • 9-.BETA.-D-RIBOFURANOSYL-6-MERCAPTOPURINE.
  • 9-.beta.-D-ribofuranosylpurine-6-thione
  • 9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-3H-purine-6-thione
  • 9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-1H-purine-6-thione
  • 9-beta-D-Ribofuranosyl-6-mercaptopurine
  • 9-beta-D-Ribofuranosyl-9H-purine-6-thiol
  • 9H-PURINE-6(1H)-THIONE, 9-.BETA.-D-RIBOFURANOSYL
  • 9H-Purine-6(1H)-thione, 9-.beta.-D-ribofuranosyl-
  • 9H-Purine-6(1H)-thione, 9-beta-D-ribofuranosyl-
  • 9H-Purine-6(1H)-thione, 9-ribofuranosyl-
  • 9H-Purine-6-thiol, 9-beta-D-ribofuranosyl-
  • 9H-Purine-6-thiol, 9-beta-D-ribofuransoyl-
  • 9H-Purine-6-thiol, 9-ribofuranosyl-
  • A-D-ribofuranoside
  • AI3-50220
  • AS-58433
  • CCRIS 2763
  • D01678
  • DSSTox_CID_26019
  • DSSTox_GSID_46019
  • DSSTox_RID_81293
  • F12892
  • Inosine, 6-thio-
  • MFCD00005743
  • Mercaptopurine ribonucleoside
  • Mercaptopurine riboside
  • NCGC00096122-03
  • NCGC00096122-05
  • NSC 4911
  • NSC-4911
  • PDSP1_001039
  • PDSP2_001023
  • Q27258956
  • Ribofuranoside, 9H-purine-6-thiol-9
  • Ribosyl-6-thiopurine
  • THIOINOSINE
  • Thioinosine
  • Thioinosine (JAN)
  • Thionosine
  • Tioinosine

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC4217548
  • CAS-574-25-4
  • UNII-46S541971T
  • AKOS015916465
  • CHEMBL448290
  • Tox21_111558
  • Tox21_111558_1
  • EINECS 209-371-5
  • SCHEMBL25230

Physico-Chemical properties

IUPAC name9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-3H-purine-6-thione
Molecular formulaC10H12N4O4S
Molecular weight284.292
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity65.66
LogP-0.9
Topological polar surface area148.5

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.