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Compound Detail

CHEMBL418509

NITROBENZYLMERCAPTOPURINE RIBONUCLEOSIDE
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O=[N+]([O-])c1ccc(CSc2ncnc3c2ncn3[C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL418509
Name NITROBENZYLMERCAPTOPURINE RIBONUCLEOSIDE
Phase Preclinical
Structure Type MOL
InChI Key DYCJFJRCWPVDHY-LSCFUAHRSA-N
6
Targets
22
Activities
3
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

419.4
MW (Da)
0.64
ALogP
11
HBA
3
HBD
156.7
PSA (Ų)
0.22
QED
1
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C17H17N5O6S
MW 419.42
Aromatic Rings 3
Heavy Atoms 29
NP-Likeness -0.19

Activity Summary

IC50 11 meas. best 9.52
Ki 10 meas. best 9.37
EC50 1 meas. best 4.6

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Equilibrative nucleoside transporter 1
CHEMBL1997
 IC50 9.52 8.6233 0.3 6
Equilibrative nucleoside transporter 1
CHEMBL1997
 Ki 9.37 9.1814 0.4 7
Unchecked
CHEMBL612545
 Ki 9.23 9.23 0.6 1
Adenosine kinase
CHEMBL2982
 Ki 5.96 5.96 1100.0 1
Plasmodium falciparum
CHEMBL364
 IC50 5.0 4.95 10000.0 2
Adenosine kinase
CHEMBL2982
 IC50 4.92 4.92 11995.0 2
Unchecked
CHEMBL612545
 EC50 4.6 4.6 25000.0 1
ATP-binding cassette sub-family C member 4
CHEMBL1743128
 IC50 4.12 4.12 75000.0 1
Solute carrier family 28 member 3
CHEMBL5707
 Ki 4.05 4.05 88050.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Equilibrative nucleoside transporter 1 IC50 = 0.3 nM 9.52 Percent inhibition against ADO transporter at 1 uM nonselective 16250647
Equilibrative nucleoside transporter 1 Ki = 0.43 nM 9.37 Inhibition of ENT1 in human K562 cells by flow cytometric assay 17636949
Unchecked Ki = 0.59 nM 9.23 Binding affinity to human erythrocyte nucleoside transport protein assessed as i... 33569941
Equilibrative nucleoside transporter 1 Ki = 0.7079 nM 9.15 Inhibition of human ENT1 19091561
Equilibrative nucleoside transporter 1 Ki = 0.7 nM 9.15 Binding affinity to human ENT1 assessed as [3H]uridine uptake by flow cytometry 19097778
Equilibrative nucleoside transporter 1 Ki = 0.7 nM 9.15 Displacement of 5-(SAENTA)-X8-fluorescein from human ENT1 transporter in human K... 18289860
Equilibrative nucleoside transporter 1 Ki = 0.7 nM 9.15 Displacement of SAENTA-fluorescein from human ENT1 in K562 cells after 45 mins b... 17881236
Equilibrative nucleoside transporter 1 Ki = 0.7 nM 9.15 Binding affinity of compound towards Nucleoside transporter es-type by facile co... 12593662
Equilibrative nucleoside transporter 1 Ki = 0.7 nM 9.15 Displacement of 5-(SAENTA)-X8-fluorescein from K562 cell nucleoside transporter 15081020
Equilibrative nucleoside transporter 1 IC50 = 1.0 nM 9.0 Inhibition of ENT1 (unknown origin) 34825182
Equilibrative nucleoside transporter 1 IC50 = 2.6 nM 8.59 Inhibition of the equilibrative nucleoside transporter (ENT1, SLC29A1) as assess... 31551431
Equilibrative nucleoside transporter 1 IC50 = 3.6 nM 8.44 Affinity On-target Cellular interaction: (Inhibition of uridine influx (10 uM) m... -
Equilibrative nucleoside transporter 1 IC50 = 7.6 nM 8.12 Inhibition of ENT1 in human K562 cells by flow cytometric assay 17636949
Equilibrative nucleoside transporter 1 IC50 = 8.511 nM 8.07 Binding affinity to ENT1 transporter 18289860
Adenosine kinase Ki = 1100.0 nM 5.96 Inhibition of Toxoplasma gondii adenosine kinase -
Plasmodium falciparum IC50 = 10000.0 nM 5.0 Antiplasmodial activity against Plasmodium falciparum 7G8 after 72 hrs by SYBR g... 19734910
Adenosine kinase IC50 = 12000.0 nM 4.92 Inhibition of Toxoplasma gondii adenosine kinase -
Adenosine kinase IC50 = 11994.99 nM 4.92 Inhibition of Toxoplasma gondii adenosine kinase -
Plasmodium falciparum IC50 = 12589.25 nM 4.9 Antiplasmodial activity against Plasmodium falciparum W2 after 72 hrs by SYBR gr... 19734910
Unchecked EC50 = 25000.0 nM 4.6 Inhibition of Escherichia coli shiga toxin 32648758

Literature References

PubMed DOI Target Context # Activities
17636949 10.1021/jm070311l Equilibrative nucleoside transporter 1 3
- 10.1007/s00044-011-9554-z Adenosine kinase 3
19574048 10.1016/j.bmcl.2009.06.056 Equilibrative nucleoside transporter 1 3
18289860 10.1016/j.bmc.2008.01.044 Equilibrative nucleoside transporter 1 2
19734910 10.1038/nchembio.215 Plasmodium falciparum 2
- 10.6019/CHEMBL5724796 Bromodomain-containing protein 4 1
15055998 10.1021/jm030537y Adenosine kinase 1
34825182 10.1039/D1MD00167A Sodium/nucleoside cotransporter 1 1
34825182 10.1039/D1MD00167A Equilibrative nucleoside transporter 1 1
31551431 10.1038/s41598-019-48829-3 Equilibrative nucleoside transporter 1 1
32648758 10.1021/acs.jmedchem.0c00298 Unchecked 1
30964283 10.1021/acs.jmedchem.9b00182 Plasmodium falciparum 1
12695538 10.1124/mol.63.5.1094 ATP-binding cassette sub-family C member 4 1
17417631 10.1038/nchembio873 Unchecked 1
19091561 10.1016/j.bmcl.2008.11.092 Equilibrative nucleoside transporter 1 1
19097778 10.1016/j.bmcl.2008.11.112 Equilibrative nucleoside transporter 1 1
19097778 10.1016/j.bmcl.2008.11.112 Solute carrier family 28 member 3 1
17881236 10.1016/j.bmc.2007.08.058 Equilibrative nucleoside transporter 1 1
16250647 10.1021/jm058018d Equilibrative nucleoside transporter 1 1
12593662 10.1021/jm020405p Equilibrative nucleoside transporter 1 1

Data from ChEMBL 36 via Core Engine