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Compound Detail

CHEMBL8488

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Cn1c(=O)c2nc(-c3ccc(S(=O)(=O)O)cc3)[nH]c2n(C)c1=O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL8488
Phase Preclinical
Structure Type MOL
InChI Key LXJSJIXZOAMHTG-UHFFFAOYSA-N
10
Targets
28
Activities
2
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

336.3
MW (Da)
-0.13
ALogP
7
HBA
2
HBD
127.0
PSA (Ų)
0.63
QED
0
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C13H12N4O5S
MW 336.33
Aromatic Rings 3
Heavy Atoms 23
NP-Likeness -0.82

Activity Summary

Ki 19 meas. best 6.0
IC50 9 meas. best 7.66

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Adenosine receptor A1
CHEMBL318
 IC50 7.66 7.005 22.0 2
Adenosine receptor A1
CHEMBL4975
 IC50 7.66 7.66 21.9 1
Adenosine receptor A1
CHEMBL318
 Ki 6.0 5.4929 1000.0 7
Adenosine receptor A2b
CHEMBL255
 Ki 5.88 5.88 1330.0 3
Adenosine receptor A1
CHEMBL226
 Ki 5.35 5.35 4500.0 1
Adenosine A2 receptor
CHEMBL2094117
 Ki 5.3 5.3 5000.0 1
Adenosine A2 receptor
CHEMBL2094257
 Ki 5.26 5.26 5500.0 1
Adenosine receptor A2a
CHEMBL302
 Ki 5.24 4.98 5800.0 3
Adenosine receptor A3
CHEMBL256
 Ki 5.23 5.095 5890.0 2
Adenosine receptor A2a
CHEMBL2605
 Ki 5.2 5.2 6300.0 1
Plasmodium falciparum
CHEMBL364
 IC50 4.9 4.85 12589.2 6

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Adenosine receptor A1 IC50 = 22.0 nM 7.66 Binding affinity against adenosine A1 receptor in rat brain membrane preparation... 3806606
Adenosine receptor A1 IC50 = 21.9 nM 7.66 Binding affinity against bovine brain adenosine A1 receptor by using N6-[3H]- cy... 2991519
Adenosine receptor A1 IC50 = 448.0 nM 6.35 Binding affinity against rat brain adenosine A1 receptor using N6-[3H]- cyclohex... 2991519
Adenosine receptor A1 Ki = 1000.0 nM 6.0 Binding affinity for adenosine A1 receptor from rat brain membranes using [3H]PI... 8410976
Adenosine receptor A1 Ki = 1000.0 nM 6.0 Inhibition of 1 nM [3H]- N6-(phenylisopropyl) adenosine binding to Adenosine A1 ... 2724296
Adenosine receptor A2b Ki = 1330.0 nM 5.88 Displacement of [125I]ABOPX from human recombinant adenosine A2B receptor expres... 16821798
Adenosine receptor A2b Ki = 1330.0 nM 5.88 Binding affinity at human Adenosine A2B receptor expressed in HEK293 cells, usin... 12014951
Adenosine receptor A2b Ki = 1330.0 nM 5.88 Binding affinity for human HEK293 adenosine A2B receptor using [125I]ABOPX in CH... 14761205
Adenosine receptor A1 Ki = 1500.0 nM 5.82 Inhibition of 1 nM [3H]- N6 -(phenylisopropyl) adenosine binding to Adenosine A1... 2724296
Adenosine receptor A1 Ki = 2600.0 nM 5.58 Binding affinity against adenosine A1 receptor using [3H]-CHA or [3H]PIA as radi... 1738138
Adenosine receptor A1 Ki = 4500.0 nM 5.35 Antagonism of binding of 1 nM [3H]cyclohexyladenosine to adenosine A1 receptors ... 2984420
Adenosine receptor A1 Ki = 4500.0 nM 5.35 Displacement of [3H]cyclohexyladen from A1 adenosine receptor derived from rat c... 34019396
Adenosine A2 receptor Ki = 5000.0 nM 5.3 Inhibition of the stimulation by 5'-(N-ethylcarbamoyl) adenosine of adenyl cycla... 2724296
Adenosine A2 receptor Ki = 5500.0 nM 5.26 Inhibition of the stimulation by 5'-(N-ethylcarbamoyl) adenosine of adenyl cycla... 2724296
Adenosine receptor A2a Ki = 5800.0 nM 5.24 Binding affinity for adenosine A2A receptor from rat brain membranes using [3H]C... 8410976
Adenosine receptor A3 Ki = 5890.0 nM 5.23 Displacement of [125I]AB-MECA from human recombinant adenosine A3 receptor expre... 16821798
Adenosine receptor A2a Ki = 6300.0 nM 5.2 Antagonism of cyclic [3H]AMP accumulation in guinea pig cerebral cortical slices... 2984420
Adenosine receptor A3 Ki = 11000.0 nM 4.96 Binding affinity for human adenosine A3 receptor using [3H]-PBS-11 in CHO cell m... 14761205
Plasmodium falciparum IC50 = 12589.25 nM 4.9 Antiplasmodial activity against Plasmodium falciparum HB3 after 72 hrs by SYBR g... 19734910
Plasmodium falciparum IC50 = 12589.25 nM 4.9 Antiplasmodial activity against Plasmodium falciparum 7G8 after 72 hrs by SYBR g... 19734910

Literature References

PubMed DOI Target Context # Activities
19734910 10.1038/nchembio.215 Plasmodium falciparum 6
2991519 10.1021/jm00146a016 Adenosine receptor A1 2
16821798 10.1021/jm060277v Adenosine receptor A2a 2
16821798 10.1021/jm060277v Adenosine receptor A1 2
3806606 10.1021/jm00384a016 Adenosine receptor A1 2
2724296 10.1021/jm00126a014 Adenosine A2 receptor 2
2724296 10.1021/jm00126a014 Adenosine receptor A1 2
2579237 10.1021/jm00381a019 Sodium channel alpha subunits; brain (Types I, II, III) 2
1738138 10.1021/jm00081a001 Adenosine receptor A1 1
1738138 10.1021/jm00081a001 Adenosine A2 receptor 1
1738138 10.1021/jm00081a001 Adenosine receptors; A1 & A2 1
14761205 10.1021/jm0310030 Adenosine receptor A1 1
12014951 10.1021/jm0104318 Adenosine receptor A2b 1
2984420 10.1021/jm00382a018 Adenosine receptor A1 1
2984420 10.1021/jm00382a018 Adenosine receptor A2a 1
2984420 10.1021/jm00382a018 Unchecked 1
2984420 10.1021/jm00382a018 No relevant target 1
34019396 10.1021/acs.jmedchem.1c00261 Adenosine receptor A1 1
14761205 10.1021/jm0310030 Adenosine receptor A3 1
14761205 10.1021/jm0310030 Adenosine receptor A2b 1

Data from ChEMBL 36 via Core Engine