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Compound Detail

CHEMBL1257013

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OC[C@H]1O[C@@H](n2cnc3c(NCCc4ccccc4)ncnc32)[C@H](O)[C@@H]1O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1257013
Phase Preclinical
Structure Type MOL
InChI Key LGZYEDZSPHLISU-SCFUHWHPSA-N
11
Targets
26
Activities
4
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

371.4
MW (Da)
0.09
ALogP
9
HBA
4
HBD
125.5
PSA (Ų)
0.48
QED
0
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C18H21N5O4
MW 371.40
Aromatic Rings 3
Heavy Atoms 27
NP-Likeness 0.50

Activity Summary

EC50 11 meas. best 6.05
Ki 11 meas. best 8.68
IC50 3 meas. best 5.6
Kd 1 meas. best 5.54

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Adenosine receptor A3
CHEMBL256
 Ki 8.68 8.68 2.1 1
Adenosine receptor A1
CHEMBL318
 Ki 8.39 7.95 4.1 4
Adenosine receptor A1
CHEMBL226
 Ki 7.89 7.89 12.9 1
Adenosine A2 receptor
CHEMBL2094117
 Ki 6.8 6.795 160.0 2
Adenosine receptor A2a
CHEMBL302
 Ki 6.79 6.79 161.0 1
Adenosine receptor A3
CHEMBL3360
 Ki 6.62 6.62 240.0 1
Adenosine receptor A2a
CHEMBL251
 Ki 6.17 6.17 676.0 1
Unchecked
CHEMBL612545
 EC50 6.05 5.385 893.0 2
Enterovirus A71
CHEMBL612436
 EC50 5.75 5.4129 1800.0 7
Unchecked
CHEMBL612545
 IC50 5.6 5.6 2500.0 1
Unchecked
CHEMBL612545
 Kd 5.54 5.54 2900.0 1
BJ
CHEMBL614358
 EC50 4.82 4.635 15212.0 2
Plasmodium falciparum
CHEMBL364
 IC50 4.8 4.8 15848.9 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Adenosine receptor A3 Ki = 2.1 nM 8.68 Displacement of [125I]I-AB-MECA from recombinant human adenosine A3 receptor exp... 30568760
Adenosine receptor A1 Ki = 4.1 nM 8.39 Binding affinity for Adenosine A1 receptor using [3H]- CHA or [3H]- PIA 1738138
Adenosine receptor A1 Ki = 12.7 nM 7.9 Binding affinity to adenosine A1 receptor in rat whole brain membranes by [3H]N6... 2888894
Adenosine receptor A1 Ki = 12.9 nM 7.89 Displacement of [3H]DPCPX from recombinant human A1 receptor expressed in CHO ce... 30568760
Adenosine receptor A1 Ki = 13.0 nM 7.89 Binding affinity towards adenosine A1 receptor on rat whole brain membrane using... 3336027
Adenosine receptor A1 Ki = 24.0 nM 7.62 Displacement of [3H]DPCPX from rat A1 receptor 30568760
Adenosine A2 receptor Ki = 160.0 nM 6.8 Binding affinity towards adenosine A2 receptor on rat striatal membrane using [3... 3336027
Adenosine receptor A2a Ki = 161.0 nM 6.79 Displacement of [3H]ZM241385 from rat A2A receptor 30568760
Adenosine A2 receptor Ki = 161.0 nM 6.79 Binding affinity to A2 adenosine receptor in rat striatal membranes by [3H]NECA ... 2888894
Adenosine receptor A3 Ki = 240.0 nM 6.62 Displacement of [125I]I-AB-MECA from rat adenosine A3 receptor 30568760
Adenosine receptor A2a Ki = 676.0 nM 6.17 Displacement of [3H]ZM241385 from human A2A receptor expressed in HEK293 cell me... 30568760
Unchecked EC50 = 893.0 nM 6.05 PUBCHEM_BIOASSAY: Luminescence Cell-Based Dose Confirmation HTS to Identify Inhi... -
Enterovirus A71 EC50 = 1800.0 nM 5.75 Antiviral activity against Enterovirus 71 infected in human RD cells assessed as... 26854380
Enterovirus A71 EC50 = 1900.0 nM 5.72 Antiviral activity against Enterovirus 71 clinical isolate H08300 461#812 infect... 26854380
Unchecked IC50 = 2500.0 nM 5.6 Inhibition of Clostridioides difficile-specific DNA adenine methyltransferase me... 36581322
Enterovirus A71 EC50 = 2700.0 nM 5.57 Antiviral activity against Enterovirus 71 clinical isolate TW/1956/05 infected i... 26854380
Unchecked Kd = 2900.0 nM 5.54 Binding affinity to Clostridioides difficile-specific DNA adenine methyltransfer... 36581322
Enterovirus A71 EC50 = 3700.0 nM 5.43 Antiviral activity against Enterovirus 71 isolate TW/2429/04 infected in human R... 26854380
Enterovirus A71 EC50 = 5600.0 nM 5.25 Antiviral activity against Enterovirus 71 clinical isolate TW/96016/08 infected ... 26854380
Enterovirus A71 EC50 = 8200.0 nM 5.09 Antiviral activity against Enterovirus 71 clinical isolate 11316 infected in hum... 26854380

Literature References

PubMed DOI Target Context # Activities
26854380 10.1016/j.ejmech.2016.01.036 Enterovirus A71 7
36581322 10.1021/acs.jmedchem.2c01789 Unchecked 5
30568760 10.1039/C8MD00317C Adenosine receptor A2a 2
30568760 10.1039/C8MD00317C Adenosine receptor A3 2
2888894 10.1021/jm00393a003 Mus musculus 2
3336027 10.1021/jm00396a044 Adenosine receptor A1 2
3336027 10.1021/jm00396a044 Adenosine A2 receptor 2
30568760 10.1039/C8MD00317C Adenosine receptor A1 2
3012086 10.1021/jm00156a016 Adenosine A2 receptor 2
1738138 10.1021/jm00081a001 Adenosine receptor A1 1
26854380 10.1016/j.ejmech.2016.01.036 RD 1
17417631 10.1038/nchembio873 Unchecked 1
19734910 10.1038/nchembio.215 Plasmodium falciparum 1
3012086 10.1021/jm00156a016 ADMET 1
11063610 10.1021/jm000287a Phosphoglycerate kinase 1
2999397 10.1021/jm00149a016 No relevant target 1
2999397 10.1021/jm00149a016 Alpha-1A adrenergic receptor 1
2999397 10.1021/jm00149a016 ADMET 1
3336027 10.1021/jm00396a044 Adenosine receptors; A1 & A2 1
2888894 10.1021/jm00393a003 Adenosine A2 receptor 1

Data from ChEMBL 36 via Core Engine