6-Mercaptopurine ribonucleoside 5'-diphosphate

A summary of the most common chemical descriptors (InChI Key and SMILES codes) for 6-Mercaptopurine ribonucleoside 5'-diphosphate are summarized together with 3D and 2D structures and relevant physico-chemical properties.

What is the 6-Mercaptopurine ribonucleoside 5'-diphosphate?

The molecule 6-Mercaptopurine ribonucleoside 5'-diphosphate presents a molecular formula of C10H14N4O10P2S and its IUPAC name is [(2R,3S,4R,5R)-3,4-dihydroxy-5-(6-sulfanylidene-3H-purin-9-yl)oxolan-2-yl]methyl phosphono hydrogen phosphate.

6-Mercaptopurine ribonucleoside 5'-diphosphate (6-MP-RNP) is a nucleotide analogue and prodrug of 6-mercaptopurine (6-MP). It is used as an antineoplastic agent in the treatment of leukemia and lymphoma. 6-MP-RNP is metabolized to 6-MP by purine nucleoside phosphorylase (PNP). PNP is a ubiquitous enzyme that belongs in most tissues. 6-MP-RNP is rapidly dephosphorylated to 6-MP in erythrocytes and leukocytes. The half-life of 6-MP-RNP in erythrocytes is approximately 2 hours. In contrast, the half-life of 6-MP-RNP in leukocytes is much longer and has not been determined..

6-MP-RNP is phosphorylated to 6-MP by adenosine kinase (AK) in vitro. AK is a ubiquitous enzyme that belongs in most tissues. The half-life of 6-MP-RNP in erythrocytes is approximately 2 hours. In contrast, the half-life of 6-MP-RNP in leukocytes is much longer and has not been determined. 6-MP is a purine analogue that is metabolized to 6-thiouric acid (6-TUA) and then to 6-methylmercaptopurine (6-MMP). 6-MMP is an inhibitor of purine biosynthesis and is the active metabolite of 6-MP. 6-MMP is also a substrate for thiopurine S-methyltransferase (TPMT). TPMT is a polymorphic enzyme that catalyzes the S-methylation of 6-MMP to form 7-methylxanthine (7-MX). 7-MX is a xanthine derivative that is a potent inhibitor of xanthine oxidase (XO). XO is a molybdenum-containing enzyme that catalyzes the oxidation of xanthine to uric acid..

The pharmacokinetics of 6-MP-RNP have been studied in patients with leukemia. The bioavailability of 6-MP-RNP is approximately 100%. The half-life of 6-MP-RNP in erythrocytes is approximately 2 hours. In contrast, the half-life of 6-MP-RNP in leukocytes is much longer and has not been determined. The pharmacokinetics of 6-MP-RNP are not affected by the route of administration..

6-MP-RNP is an antineoplastic agent that is used in the treatment of leukemia and lymphoma. It is metabolized to 6-MP, which is the active metabolite. 6-MP is an inhibitor of purine biosynthesis and is a substrate for thiopurine S-methyltransferase (TPMT). TPMT is a polymorphic enzyme that catalyzes the S-methylation of 6-MP to form 7-methylxanthine (7-MX). 7-MX is a xanthine derivative that is a potent inhibitor of xanthine oxidase (XO). The pharmacokinetics of 6-MP-RNP are not affected by the route of administration..

3D structure

Cartesian coordinates

Geometry of 6-Mercaptopurine ribonucleoside 5'-diphosphate in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.

2D drawing

 

6-Mercaptopurine ribonucleoside 5'-diphosphate MHJZYMCYLFGDRD-KQYNXXCUSA-N chemical compound 2D structure molecule svg
6-Mercaptopurine ribonucleoside 5'-diphosphate

 

Molecule descriptors

 
IUPAC name[(2R,3S,4R,5R)-3,4-dihydroxy-5-(6-sulfanylidene-3H-purin-9-yl)oxolan-2-yl]methyl phosphono hydrogen phosphate
InChI codeInChI=1S/C10H14N4O10P2S/c15-6-4(1-22-26(20,21)24-25(17,18)19)23-10(7(6)16)14-3-13-5-8(14)11-2-12-9(5)27/h2-4,6-7,10,15-16H,1H2,(H,20,21)(H,11,12,27)(H2,17,18,19)/t4-,6-,7-,10-/m1/s1
InChI KeyMHJZYMCYLFGDRD-KQYNXXCUSA-N
SMILESO=P(O)(O)O[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.

  • 6-Mercaptopurine ribonucleoside 5'-diphosphate
  • 6-Mpr 5'-DP
  • 6-Thioinosine 5'-diphosphate
  • 6-Thioinosine-5'-diphosphate
  • 6-thioinosine diphosphate
  • 805-63-0
  • Inosine 5'-(trihydrogen diphosphate), 6-thio-
  • Q27149656

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • DTXSID70230372
  • CHEBI:80610
  • SCHEMBL1905818

Physico-Chemical properties

IUPAC name[(2R,3S,4R,5R)-3,4-dihydroxy-5-(6-sulfanylidene-3H-purin-9-yl)oxolan-2-yl]methyl phosphono hydrogen phosphate
Molecular formulaC10H14N4O10P2S
Molecular weight444.251
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity87.34
LogP-1.0
Topological polar surface area265.0

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.