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Compound Detail

CHEMBL60662

6-BENZYLTHIOINOSINE
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OC[C@H]1O[C@@H](n2cnc3c(SCc4ccccc4)ncnc32)[C@H](O)[C@@H]1O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL60662
Name 6-BENZYLTHIOINOSINE
Phase Preclinical
Structure Type MOL
InChI Key OMJRXFOHHLLDFR-LSCFUAHRSA-N
3
Targets
10
Activities
2
Assay Types
0
PK Parameters
11
Publications
0
Known Names

Molecular Properties

374.4
MW (Da)
0.73
ALogP
9
HBA
3
HBD
113.5
PSA (Ų)
0.44
QED
0
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C17H18N4O4S
MW 374.42
Aromatic Rings 3
Heavy Atoms 26
NP-Likeness 0.17

Activity Summary

IC50 5 meas. best 5.77
Ki 5 meas. best 7.7

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Equilibrative nucleoside transporter 1
CHEMBL1997
 Ki 7.7 7.49 19.9 2
Equilibrative nucleoside transporter 1
CHEMBL1997
 IC50 5.77 5.77 1698.2 1
Adenosine kinase
CHEMBL2982
 Ki 5.62 4.96 2400.0 3
Adenosine kinase
CHEMBL2982
 IC50 5.03 5.03 9289.7 2
Bacillus anthracis
CHEMBL613904
 IC50 4.3 4.3 50000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Equilibrative nucleoside transporter 1 Ki = 19.95 nM 7.7 Inhibition of human ENT1 19091561
Equilibrative nucleoside transporter 1 Ki = 53.0 nM 7.28 Inhibition of [3H]NBTI binding to equilibrative nucleoside transport protein 1 (... 15634027
Equilibrative nucleoside transporter 1 IC50 = 1698.24 nM 5.77 Binding affinity to ENT1 transporter 18289860
Adenosine kinase Ki = 2400.0 nM 5.62 Inhibition of Toxoplasma gondii adenosine kinase -
Adenosine kinase IC50 = 9289.66 nM 5.03 Inhibition of Toxoplasma gondii adenosine kinase -
Adenosine kinase IC50 = 9300.0 nM 5.03 Inhibition of Toxoplasma gondii adenosine kinase -
Adenosine kinase Ki = 14300.0 nM 4.84 Binding affinity to Toxoplasma gondii adenosine kinase after 20 mins by radioact... 20456959
Adenosine kinase Ki = 37700.0 nM 4.42 Binding affinity to purified Toxoplasma gondii adenosine kinase 18563892
Bacillus anthracis IC50 = 50000.0 nM 4.3 Inhibition of inosine/L-alanine-induced Bacillus anthracis Sterne 34F2 spore ger... 20921305

Literature References

PubMed DOI Target Context # Activities
- 10.1007/s00044-011-9554-z Adenosine kinase 3
20921305 10.1128/aac.01029-10 Bacillus anthracis 2
15055998 10.1021/jm030537y Adenosine kinase 1
15634027 10.1021/jm049303k Equilibrative nucleoside transporter 1 1
18289860 10.1016/j.bmc.2008.01.044 Equilibrative nucleoside transporter 1 1
18563892 10.1021/jm800201s Adenosine kinase 1
19091561 10.1016/j.bmcl.2008.11.092 Equilibrative nucleoside transporter 1 1
20456959 10.1016/j.bmc.2010.04.003 Adenosine kinase 1
20921305 10.1128/aac.01029-10 J774.A1 1
22884224 10.1016/j.ejmech.2012.07.031 Pro-adrenomedullin 1
38739840 10.1021/acs.jmedchem.3c01267 AMP-activated protein kinase (AMPK) alpha-1/beta-1/gamma-1 1

Data from ChEMBL 36 via Core Engine