Thioinosinic acid

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

What is the Thioinosinic acid?

The molecule Thioinosinic acid presents a molecular formula of C10H13N4O7PS and its IUPAC name is [(2R,3S,4R,5R)-3,4-dihydroxy-5-(6-sulfanylidene-3H-purin-9-yl)oxolan-2-yl]methyl dihydrogen phosphate.

Thioinosinic acid (TIA) is a molecule composed of sulfur, nitrogen, and oxygen. It is an important intermediate in the metabolism of thiamin (vitamin B1). TIA is formed by the action of thiamin diphosphate (TDP) on thiamin pyrophosphate (TPP). TIA is then converted to thiamin triphosphate (TTP) by thiamin pyrophosphokinase..

TIA is a coenzyme in the decarboxylation of α-keto acids. TIA is also required for the synthesis of certain nucleotides, such as thymidine monophosphate (TMP)..

TIA is a colorless, water-soluble solid. It is insoluble in organic solvents. TIA has a strong odor..

TIA is considered to be nontoxic and is not known to cause any adverse effects in humans..

3D structure

Cartesian coordinates

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

2D drawing

 

Thioinosinic acid ZKRFOXLVOKTUTA-KQYNXXCUSA-N chemical compound 2D structure molecule svg
Thioinosinic acid

 

Molecule descriptors

 
IUPAC name[(2R,3S,4R,5R)-3,4-dihydroxy-5-(6-sulfanylidene-3H-purin-9-yl)oxolan-2-yl]methyl dihydrogen phosphate
InChI codeInChI=1S/C10H13N4O7PS/c15-6-4(1-20-22(17,18)19)21-10(7(6)16)14-3-13-5-8(14)11-2-12-9(5)23/h2-4,6-7,10,15-16H,1H2,(H,11,12,23)(H2,17,18,19)/t4-,6-,7-,10-/m1/s1
InChI KeyZKRFOXLVOKTUTA-KQYNXXCUSA-N
SMILESO=P(O)(O)OC[C@H]1O[C@@H](n2cnc3c(S)ncnc32)[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)-3,4-DIHYDROXY-5-(6-SULFANYL-9H-PURIN-9-YL)OXOLAN-2-YL)METHOXY)PHOSPHONIC ACID
  • ((2R,3S,4R,5R)-3,4-DIHYDROXY-5-(6-SULFANYLIDENE-3H-PURIN-9-YL)OXOLAN-2-YL)METHYL DIHYDROGEN PHOSPHATE
  • ((2R,3S,4R,5R)-3,4-Dihydroxy-5-(6-mercapto-9H-purin-9-yl)tetrahydrofuran-2-yl)methyl dihydrogen phosphate
  • 1-(6-MERCAPTO-9H-PURIN-9-YL)-1-DEOXY-.BETA.-D-RIBOFURANOSE 5-PHOSPHORIC ACID
  • 5'-Inosinic acid, 6-thio-
  • 53-83-8
  • 6-MERCAPTOPURINE RIBONUCLEOSIDE MONOPHOSPHATE
  • 6-Mercaptopurine Ribonucleoside 5'-Phosphate
  • 6-Mercaptopurine ribonucleotide
  • 6-Mercaptopurine riboside 5'-monophosphate
  • 6-Mercaptopurine riboside 5'-phosphate
  • 6-Mercaptopurine riboside-5-phosphate
  • 6-Mercaptopurine ribotide
  • 6-Mercaptopurine-riboside-5'-monophosphate
  • 6-Thio-5'-inosinic Acid
  • 6-Thio-IMP
  • 6-Thioinosine 5'-monophosphate
  • 6-Thioinosine 5'-phosphate
  • 6-Thioinosine Phosphate
  • 6-Thioinosine-5'-monophosphate
  • 6-Thioinosinic Acid
  • 76CK4YA5ZP
  • 9-(5-O-(DIHYDROXYPHOSPHINYL)-.BETA.-D-RIBOFURANOSYL)-1,6-DIHYDRO-9H-PURINE-6-THIONE
  • 9-(5-O-PHOSPHONO-.BETA.-D-RIBOFURANOSYL)-1,9-DIHYDRO-6H-PURINE-6-THIONE
  • 9-(5-Phospho-1-ribofuranosyl)-6-mercaptopurine
  • 9-(5-phosphoribofuranosyl)-6-mercaptopurine
  • 9H-PURINE-6-THIOL, 9-.BETA.-D-RIBOFURANOSYL-, 5'-PHOSPHATE
  • 9H-Purine-6-thiol, 9-.beta.-D-ribofuranosyl-, 5'-(dihydrogen phosphate)
  • 9H-Purine-6-thiol, 9-beta-D-ribofuranosyl-, 5'-(dihydrogen phosphate)
  • C04646
  • J213.539F
  • NSC 520722
  • NSC-520722
  • Q6593516
  • TIMP
  • Thio-IMP
  • Thioinosinic acid
  • W-203028
  • [(2R,3S,4R,5R)-3,4-dihydroxy-5-(6-sulfanylidene-3H-purin-9-yl)oxolan-2-yl]methyl dihydrogen phosphate
  • [(2R,3S,4R,5R)-3,4-dihydroxy-5-(6-thioxo-3H-purin-9-yl)tetrahydrofuran-2-yl]methyl dihydrogen phosphate

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC4096488
  • UNII-76CK4YA5ZP
  • DTXSID80926618
  • CHEMBL1237125
  • CHEBI:2332
  • EINECS 200-183-9
  • SCHEMBL379365

Physico-Chemical properties

IUPAC name[(2R,3S,4R,5R)-3,4-dihydroxy-5-(6-sulfanylidene-3H-purin-9-yl)oxolan-2-yl]methyl dihydrogen phosphate
Molecular formulaC10H13N4O7PS
Molecular weight364.272
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity76.43
LogP-1.2
Topological polar surface area208.7

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.