6-Thioguanosine triphosphate

A summary of the most common chemical descriptors (InChI Key and SMILES codes) for 6-Thioguanosine triphosphate are summarized together with 3D and 2D structures and relevant physico-chemical properties.

What is the 6-Thioguanosine triphosphate?

The molecule 6-Thioguanosine triphosphate presents a molecular formula of C10H16N5O13P3S and its IUPAC name is [[(2R,3S,4R,5R)-5-(2-amino-6-sulfanylidene-3H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] phosphono hydrogen phosphate.

6-Thioguanosine triphosphate (6-TGTP) is a nucleotide derivative of guanosine that contains a sulfur atom in place of the oxygen atom at the 6-position. It belongs in some bacteria and archaea. 6-TGTP is a substrate for thioredoxin reductase (TrxR), an enzyme that plays a role in redox homeostasis. TrxR uses 6-TGTP to regenerate thioredoxin (Trx), a small protein that acts as a coenzyme in various redox reactions. 6-TGTP is also a substrate for sulfiredoxin (Srx), another enzyme involved in redox homeostasis. Srx uses 6-TGTP to regenerate sulfite, a small molecule that is used in the biosynthesis of cysteine. 6-TGTP is also a substrate for adenosine kinase (AK), an enzyme that phosphorylates adenosine to adenosine monophosphate (AMP). AK belongs in all cells, including bacteria, archaea, and eukaryotes. 6-TGTP is also a substrate for inosine monophosphate cyclohydrolase (IMPCH), an enzyme that catalyzes the conversion of inosine monophosphate (IMP) to xanthosine monophosphate (XMP). IMPCH belongs in all cells, including bacteria, archaea, and eukaryotes. 6-TGTP is also a substrate for adenosine deaminase (ADA), an enzyme that catalyzes the conversion of adenosine to inosine. ADA belongs in all cells, including bacteria, archaea, and eukaryotes. 6-TGTP is also a substrate for guanylate kinase (GK), an enzyme that phosphorylates guanosine to guanosine monophosphate (GMP). GK belongs in all cells, including bacteria, archaea, and eukaryotes. 6-TGTP is also a substrate for thymidine kinase (TK), an enzyme that phosphorylates thymidine to thymidine monophosphate (TMP). TK belongs in all cells, including bacteria, archaea, and eukaryotes. 6-TGTP is also a substrate for xanthine oxidase (XO), an enzyme that catalyzes the oxidation of xanthine to uric acid. XO belongs in all cells, including bacteria, archaea, and eukaryotes..

3D structure

Cartesian coordinates

Geometry of 6-Thioguanosine triphosphate in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.

2D drawing

 

6-Thioguanosine triphosphate QENYANNAQSWPLM-UUOKFMHZSA-N chemical compound 2D structure molecule svg
6-Thioguanosine triphosphate

 

Molecule descriptors

 
IUPAC name[[(2R,3S,4R,5R)-5-(2-amino-6-sulfanylidene-3H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] phosphono hydrogen phosphate
InChI codeInChI=1S/C10H16N5O13P3S/c11-10-13-7-4(8(32)14-10)12-2-15(7)9-6(17)5(16)3(26-9)1-25-30(21,22)28-31(23,24)27-29(18,19)20/h2-3,5-6,9,16-17H,1H2,(H,21,22)(H,23,24)(H2,18,19,20)(H3,11,13,14,32)/t3-,5-,6-,9-/m1/s1
InChI KeyQENYANNAQSWPLM-UUOKFMHZSA-N
SMILESNc1nc(=S)c2ncn([C@@H]3O[C@H](CO[P@](=O)(O)O[P@](=O)(O)OP(=O)(O)O)[C@@H](O)[C@H]3O)c2[nH]1

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)-5-(2-Amino-6-thioxo-1H-purin-9(6H)-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl tetrahydrogen triphosphate
  • 17670-19-8
  • 6-SH-GTP
  • 6-Thio-GTP
  • 6-Thioguanosine triphosphate
  • 6-thioguanosine triphosphate
  • Thioguanosine 5'-triphosphate
  • [[(2R,3S,4R,5R)-5-(2-amino-6-sulfanylidene-3H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] phosphono hydrogen phosphate

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC95618747
  • DTXSID20170173
  • CHEMBL3638285
  • SCHEMBL596132

Physico-Chemical properties

IUPAC name[[(2R,3S,4R,5R)-5-(2-amino-6-sulfanylidene-3H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] phosphono hydrogen phosphate
Molecular formulaC10H16N5O13P3S
Molecular weight539.246
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity102.79
LogP-0.4
Topological polar surface area343.6

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.