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Compound Detail

CHEMBL388757

N6-BENZYLADENOSINE
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OC[C@H]1O[C@@H](n2cnc3c(NCc4ccccc4)ncnc32)[C@H](O)[C@@H]1O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL388757
Name N6-BENZYLADENOSINE
Phase Preclinical
Structure Type MOL
InChI Key MRPKNNSABYPGBF-LSCFUAHRSA-N
15
Targets
34
Activities
4
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

357.4
MW (Da)
0.05
ALogP
9
HBA
4
HBD
125.5
PSA (Ų)
0.50
QED
0
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C17H19N5O4
MW 357.37
Aromatic Rings 3
Heavy Atoms 26
NP-Likeness 0.45

Activity Summary

Ki 17 meas. best 7.38
IC50 13 meas. best 6.9
EC50 3 meas. best 6.55
Kd 1 meas. best 4.89

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Adenosine receptor A3
CHEMBL256
 Ki 7.38 6.82 41.3 2
Adenosine receptor A1
CHEMBL318
 Ki 6.92 6.655 120.0 6
Adenosine receptor A3
CHEMBL3360
 Ki 6.92 6.92 120.0 1
Adenosine receptor A1
CHEMBL318
 IC50 6.9 6.9 125.9 1
Equilibrative nucleoside transporter 1
CHEMBL4604
 Ki 6.69 6.69 203.0 1
Adenosine A2 receptor
CHEMBL2094117
 Ki 6.55 6.5275 280.0 4
Enterovirus A71
CHEMBL612436
 EC50 6.55 6.55 280.0 2
Adenosine receptor A2a
CHEMBL302
 Ki 6.54 6.335 285.0 2
Adenosine receptor A3
CHEMBL256
 EC50 6.42 6.42 384.0 1
HL-60
CHEMBL383
 IC50 6.03 6.03 940.0 1
CCRF-CEM
CHEMBL382
 IC50 5.85 5.85 1400.0 1
Unchecked
CHEMBL612545
 IC50 5.66 5.24 2200.0 2
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 5.27 5.27 5400.0 1
K562
CHEMBL385
 IC50 5.26 5.26 5500.0 1
Equilibrative nucleoside transporter 1
CHEMBL1997
 IC50 4.97 4.97 10715.2 1
Unchecked
CHEMBL612545
 Kd 4.89 4.89 13000.0 1
Platelet
CHEMBL4296519
 IC50 4.43 4.43 37120.0 1
ADMET
CHEMBL612558
 IC50 4.41 4.41 39000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Adenosine receptor A3 Ki = 41.3 nM 7.38 Inhibition of human adenosine A3 receptor 18588281
Adenosine receptor A3 Ki = 120.0 nM 6.92 Binding affinity determined by displacement of specific binding of [125I]N-(4-am... 7707320
Adenosine receptor A1 Ki = 120.0 nM 6.92 Binding affinity to adenosine A1 receptor in rat brain membranes by measuring di... 7707320
Adenosine receptor A1 Ki = 120.0 nM 6.92 Binding affinity towards adenosine A1 receptor on rat whole brain membrane using... 3336027
Adenosine receptor A1 Ki = 120.0 nM 6.92 Binding affinity to adenosine A1 receptor in rat whole brain membranes by [3H]N6... 2888894
Adenosine receptor A1 Ki = 120.0 nM 6.92 Inhibition of binding of [3H]N6-cyclohexyladenosine to adenosine A1 receptor of ... 2754691
Adenosine receptor A1 IC50 = 125.89 nM 6.9 Evaluated for binding affinity against Adenosine A1 receptor 1542091
Adenosine receptor A1 Ki = 125.0 nM 6.9 Inhibition of [3H]-CHA binding to rat brain membrane Adenosine A1 receptor 2258897
Equilibrative nucleoside transporter 1 Ki = 203.0 nM 6.69 Inhibition of [3H]S-(4-Nitrobenzyl)-6-thioinosine binding to adenosine uptake si... 7932588
Enterovirus A71 EC50 = 280.0 nM 6.55 Antiviral activity against human enterovirus 71 36455356
Adenosine A2 receptor Ki = 280.0 nM 6.55 Binding affinity towards adenosine A2 receptor on rat striatal membrane using [3... 3336027
Adenosine A2 receptor Ki = 280.0 nM 6.55 Binding affinity to A2 adenosine receptor in rat striatal membranes by [3H]NECA ... 2888894
Adenosine A2 receptor Ki = 280.0 nM 6.55 Inhibition of binding of [3H]NECA to adenosine A2 receptor of rat striatal membr... 2754691
Enterovirus A71 EC50 = 280.0 nM 6.55 Antiviral activity against Enterovirus 71 infected in human RD cells assessed as... 26854380
Adenosine receptor A2a Ki = 285.0 nM 6.54 Binding affinity to adenosine A2A receptor in rat striatal membranes by measurin... 7707320
Adenosine A2 receptor Ki = 350.0 nM 6.46 Binding of Adenosine A2 receptor in whole rat brain membrane using [3H]CHA as a ... 2258897
Adenosine receptor A3 EC50 = 384.0 nM 6.42 Effective concentration for stimulation of [35S]GTP-gamma-S, binding to human ad... 10212125
Adenosine receptor A3 Ki = 550.0 nM 6.26 Binding affinity at human Adenosine A3 receptor expressed in HEK 293 cells by [1... 10212125
Adenosine receptor A2a Ki = 733.0 nM 6.13 Displacement of [3H]-CGS- 21680 from Adenosine A2A receptor of rat striatal memb... 10212125
HL-60 IC50 = 940.0 nM 6.03 Antitumor activity against human HL60 cells after 72 hrs by Calcein AM assay 17418578

Literature References

PubMed DOI Target Context # Activities
7452700 10.1021/jm00186a031 Mus musculus 8
37248632 10.1021/acs.jmedchem.3c00555 Serine/threonine-protein kinase PINK1, mitochondrial 6
10212125 10.1021/jm981090+ Adenosine receptor A3 5
21035348 10.1016/j.bmc.2010.09.030 T-24 5
36581322 10.1021/acs.jmedchem.2c01789 Unchecked 5
18588281 10.1021/jm800205c K562 5
37248632 10.1021/acs.jmedchem.3c00555 HeLa 4
7452700 10.1021/jm00186a031 NON-PROTEIN TARGET 3
37248632 10.1021/acs.jmedchem.3c00555 Unchecked 3
3012086 10.1021/jm00156a016 Adenosine A2 receptor 2
28159412 10.1016/j.bmcl.2017.01.040 Tick-borne encephalitis virus 2
3336027 10.1021/jm00396a044 Adenosine A2 receptor 2
3336027 10.1021/jm00396a044 Adenosine receptor A1 2
2888894 10.1021/jm00393a003 Mus musculus 2
18321038 10.1021/jm701442d Adenosine receptor A2b 2
28159412 10.1016/j.bmcl.2017.01.040 Unchecked 2
9934461 10.1016/s0960-894x(98)00635-0 Unchecked 1
3336027 10.1021/jm00396a044 Adenosine receptors; A1 & A2 1
2258897 10.1021/jm00174a004 Adenosine A2 receptor 1
2258897 10.1021/jm00174a004 Adenosine receptor A1 1

Data from ChEMBL 36 via Core Engine