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Compound Detail

CHEMBL68738

N6-CYCLOPENTYLADENOSINE
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OC[C@H]1O[C@@H](n2cnc3c(NC4CCCC4)ncnc32)[C@H](O)[C@@H]1O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL68738
Name N6-CYCLOPENTYLADENOSINE
Phase Preclinical
Structure Type MOL
InChI Key SQMWSBKSHWARHU-SDBHATRESA-N

Known Names

CCPA
23
Targets
188
Activities
3
Assay Types
0
PK Parameters
20
Publications
1
Known Names

Molecular Properties

335.4
MW (Da)
-0.21
ALogP
9
HBA
4
HBD
125.5
PSA (Ų)
0.60
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C15H21N5O4
MW 335.36
Aromatic Rings 2
Heavy Atoms 24
NP-Likeness 0.65

Activity Summary

Ki 145 meas. best 9.66
IC50 27 meas. best 9.49
EC50 16 meas. best 9.72

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Adenosine receptor A1
CHEMBL226
 EC50 9.72 8.7667 0.2 3
Adenosine receptor A1
CHEMBL3688
 Ki 9.66 9.66 0.2 1
Adenosine receptor A1
CHEMBL4975
 Ki 9.52 8.5875 0.3 4
Adenosine receptor A1
CHEMBL318
 Ki 9.52 8.2936 0.3 53
Adenosine receptor A1
CHEMBL2304404
 Ki 9.49 9.49 0.3 1
Adenosine receptor A1
CHEMBL318
 IC50 9.49 7.2177 0.3 13
Adenosine receptor A1
CHEMBL226
 Ki 9.35 8.4145 0.5 11
Unchecked
CHEMBL612545
 IC50 9.3 7.5067 0.5 3
A1 adenosine receptor
CHEMBL1075029
 Ki 9.28 7.685 0.5 2
Cavia porcellus
CHEMBL369
 IC50 9.22 7.8 0.6 2
Adenosine A2 receptor
CHEMBL2094117
 Ki 8.96 6.4438 1.1 13
Adenosine receptor A1
CHEMBL226
 IC50 8.57 8.57 2.7 1
Unchecked
CHEMBL612545
 EC50 8.55 8.55 2.8 1
A1 adenosine receptor
CHEMBL1075029
 EC50 8.1 8.1 7.9 1
Unchecked
CHEMBL612545
 Ki 8.05 8.05 9.0 1
Rattus norvegicus
CHEMBL376
 IC50 8.0 7.9533 10.0 3
Adenosine receptor A1
CHEMBL2304404
 EC50 7.9 7.9 12.6 1
Adenosine receptor A1
CHEMBL318
 EC50 7.88 7.804 13.3 5
Adenosine receptor A3
CHEMBL3360
 Ki 7.58 6.9883 26.0 6
Adenosine receptor A2b
CHEMBL255
 Ki 7.37 6.02 43.0 2
Adenosine A2 receptor
CHEMBL2094257
 EC50 7.2 6.43 63.1 2
Adenosine receptor A3
CHEMBL256
 Ki 7.14 6.5739 72.0 18
Adenosine receptor A2a
CHEMBL302
 Ki 6.79 6.2369 163.0 16
Adenosine receptor A3
CHEMBL256
 EC50 6.62 5.86 242.0 2
Adenosine receptor A2a
CHEMBL251
 Ki 6.42 6.1167 385.0 12
Cavia porcellus
CHEMBL369
 EC50 6.38 6.38 420.0 1
Adenosine receptor A3
CHEMBL1075269
 Ki 6.27 6.27 534.0 1
Adenosine receptor A2a
CHEMBL2115
 Ki 6.09 6.09 808.0 1
Equilibrative nucleoside transporter 1
CHEMBL1997
 Ki 5.96 5.96 1100.0 1
Adenosine A2 receptor
CHEMBL2094117
 IC50 5.94 5.94 1160.0 1
Adenosine A2 receptor
CHEMBL2094257
 Ki 5.62 5.62 2400.0 1
Sigma non-opioid intracellular receptor 1
CHEMBL287
 Ki 5.58 5.58 2611.3 1
Plasmodium falciparum
CHEMBL364
 IC50 5.0 5.0 10000.0 1
23S rRNA methylase leader peptide
CHEMBL5291611
 IC50 4.2 4.2 63000.0 1
rRNA adenine N-6-methyltransferase
CHEMBL4251
 IC50 4.1 4.1 80000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Adenosine receptor A1 EC50 = 0.19 nM 9.72 Compound was evaluated for the Adenosine A1 receptor agonist potency. -
Adenosine receptor A1 Ki = 0.22 nM 9.66 Displacement of [3H]N6-R-phenylisopropyladenosine from mouse A1A adenosine recep... 30605331
Adenosine receptor A1 Ki = 0.3 nM 9.52 Inhibitory activity at Adenosine A1 receptor by inhibition of [3H]CHA binding to... 9572897
Adenosine receptor A1 Ki = 0.3 nM 9.52 Inhibition of [3H]CHA (N6-cyclohexyl adenosine) to rat brain membrane Adenosine ... 11881988
Adenosine receptor A1 Ki = 0.3 nM 9.52 Ability to displace the specific binding of [3H]CHA to adenosine A1 receptor fro... 10956189
Adenosine receptor A1 Ki = 0.32 nM 9.49 Inhibition of [3H]-CHA binding to rat brain membrane Adenosine A1 receptor 2258897
Adenosine receptor A1 Ki = 0.32 nM 9.49 Inhibition of N6-[3H]cyclohexyladenosine binding to guinea pig forebrain membran... 1548682
Adenosine receptor A1 IC50 = 0.3236 nM 9.49 Evaluated for binding affinity against Adenosine A1 receptor 1542091
Adenosine receptor A1 IC50 = 0.35 nM 9.46 Binding affinity to adenosine A1 receptor of rat brain membranes without NaCl by... 3351850
Adenosine receptor A1 Ki = 0.4 nM 9.4 Displacement of [3H]CCPA from adenosine A1 receptor in bovine cortical membrane 17933541
Adenosine receptor A1 Ki = 0.45 nM 9.35 Inhibition of [3H]- (R)-P1A binding to adenosine A1 receptor 1766003
Adenosine receptor A1 Ki = 0.45 nM 9.35 Displacement of [3H]R-PIA or [3H]CGS 21680 from human adenosine A1 receptor in C... 16366590
Unchecked IC50 = 0.5 nM 9.3 In vitro inhibition of isoprenaline-stimulated cAMP accumulation in DDT1-MF2 cel... 10479279
A1 adenosine receptor Ki = 0.53 nM 9.28 Displacement of [3H]CCPA from adenosine A1 receptor in pig cortical membrane 17933541
Adenosine receptor A1 Ki = 0.59 nM 9.23 Inhibition of binding of [3H]N6-cyclohexyladenosine to adenosine A1 receptor of ... 2754691
Adenosine receptor A1 Ki = 0.59 nM 9.23 Binding affinity against Adenosine A1 receptor using [3H]CHA in rat brain membra... 2909748
Adenosine receptor A1 Ki = 0.59 nM 9.23 Binding affinity against adenosine A1 receptor using [3H]-CHA or [3H]PIA as radi... 1738138
Adenosine receptor A1 Ki = 0.59 nM 9.23 Binding affinity against Adenosine A1 receptor using N6-[3H]cyclohexyladenosine ... 1548682
Adenosine receptor A1 Ki = 0.59 nM 9.23 Inhibition of [3H]PIA binding to rat cortical adenosine A1 receptor 1433217
Adenosine receptor A1 Ki = 0.589 nM 9.23 Evaluated for the binding affinity towards the Adenosine A1 receptor in corpora ... 2374150

Literature References

PubMed DOI Target Context # Activities
26392370 10.1016/j.bmc.2015.09.012 Adenosine receptor A1 11
- 10.6019/CHEMBL5058564 HEK-293T 10
1875349 10.1021/jm00112a035 Rattus norvegicus 9
- 10.6019/CHEMBL5058564 U2OS 8
9438026 10.1021/jm970508l Adenosine receptor A1 8
12238926 10.1021/jm020211+ Adenosine receptor A3 6
22738238 10.1021/jm3004834 Mus musculus 5
10841798 10.1021/jm9905965 Adenosine receptor A1 5
30881617 10.1039/C8MD00540K Adenosine receptor A1 4
8691477 10.1021/jm950267m Rattus norvegicus 4
11520205 10.1021/jm001114o Adenosine receptor A1 4
17933541 10.1016/j.bmc.2007.09.035 A1 adenosine receptor 4
20188574 10.1016/j.bmc.2010.01.072 Adenosine receptor A1 4
32631506 10.1016/j.bmcl.2020.127274 Adenosine receptor A1 4
10841798 10.1021/jm9905965 Adenosine receptor A3 3
10956189 10.1021/jm990321p Unchecked 3
3373486 10.1021/jm00401a018 Adenosine A2 receptor 3
10649980 10.1021/jm9911231 Adenosine receptor A1 3
9572897 10.1021/jm9707737 Unchecked 3
18042389 10.1016/j.bmc.2007.11.010 Adenosine receptor A1 3

Data from ChEMBL 36 via Core Engine