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Compound Detail

CHEMBL59986

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c1cncc(OC[C@@H]2CCN2)c1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL59986
Phase Preclinical
Structure Type MOL
InChI Key XKFMBGWHHBCWCD-QMMMGPOBSA-N
16
Targets
48
Activities
3
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

164.2
MW (Da)
0.82
ALogP
3
HBA
1
HBD
34.1
PSA (Ų)
0.72
QED
0
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C9H12N2O
MW 164.21
Aromatic Rings 1
Heavy Atoms 12
NP-Likeness -0.49

Activity Summary

Ki 31 meas. best 10.77
EC50 15 meas. best 8.52
IC50 2 meas. best 8.82

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Neuronal acetylcholine receptor; alpha4/beta2
CHEMBL1907596
 Ki 10.77 10.3 0.0 5
Unchecked
CHEMBL612545
 Ki 10.7 9.28 0.0 5
Neuronal acetylcholine receptor; alpha4/beta2
CHEMBL1907589
 Ki 10.4 10.3467 0.0 6
Neuronal acetylcholine receptor
CHEMBL2094110
 Ki 10.3 9.88 0.1 4
Neuronal acetylcholine receptor; alpha2/beta2
CHEMBL1907592
 Ki 10.13 10.13 0.1 1
Neuronal acetylcholine receptor; alpha3/beta2
CHEMBL1907587
 Ki 9.62 9.62 0.2 1
Neuronal acetylcholine receptor; alpha4/beta2
CHEMBL1907589
 IC50 8.82 8.82 1.5 1
Neuronal acetylcholine receptor; alpha4/beta2
CHEMBL1907596
 IC50 8.82 8.82 1.5 1
Rattus norvegicus
CHEMBL376
 EC50 8.52 8.52 3.0 1
Neuronal acetylcholine receptor; alpha4/beta4
CHEMBL1907595
 Ki 8.15 8.15 7.1 1
Neuronal acetylcholine receptor; alpha3/beta4
CHEMBL1907593
 Ki 7.14 7.14 72.0 1
Neuronal acetylcholine receptor subunit alpha-7
CHEMBL2492
 Ki 6.83 6.83 148.0 4
Acetylcholine receptor; alpha1/beta1/delta/gamma
CHEMBL1907588
 Ki 6.5 6.5 314.0 2
Acetylcholine receptor subunit alpha
CHEMBL3097
 Ki 6.5 6.5 314.0 1
K177 cell line
CHEMBL614687
 EC50 6.17 6.165 680.0 2
Neuronal acetylcholine receptor subunit alpha-3
CHEMBL3068
 EC50 6.16 6.16 700.0 1
Neuronal acetylcholine receptor; alpha3/beta4
CHEMBL1907594
 EC50 6.16 6.16 700.0 1
Neuronal acetylcholine receptor; alpha4/beta2
CHEMBL1907589
 EC50 6.16 6.1575 700.0 4
IMR-32
CHEMBL614585
 EC50 6.16 6.16 700.0 1
Unchecked
CHEMBL612545
 EC50 6.1 6.1 800.0 2
Neuronal acetylcholine receptor subunit alpha-7
CHEMBL2492
 EC50 5.05 5.05 8900.0 3

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Neuronal acetylcholine receptor; alpha4/beta2 Ki = 0.017 nM 10.77 Binding affinity for alpha4 beta-2 nAChR using [3H]epibatidine in rat brain 9733494
Unchecked Ki = 0.02 nM 10.7 Binding affinity to rat brain alpha4beta2* nAChR 24901260
Unchecked Ki = 0.02 nM 10.7 Binding affinity to human brain alpha3beta4* nAChR 24901260
Unchecked Ki = 0.04 nM 10.4 Binding affinity to human brain alpha4beta2* nAChR 24901260
Neuronal acetylcholine receptor; alpha4/beta2 Ki = 0.04 nM 10.4 Inhibition of alpha4beta2 nicotinic acetylcholine receptor (unknown origin) -
Neuronal acetylcholine receptor; alpha4/beta2 Ki = 0.04 nM 10.4 Binding affinity to alpha4beta2 nAChR in human brain 23092294
Neuronal acetylcholine receptor; alpha4/beta2 Ki = 0.04 nM 10.4 Compound was evaluated for its ability to displace [3H]cytisine from K177 cells ... 9484491
Neuronal acetylcholine receptor; alpha4/beta2 Ki = 0.05 nM 10.3 Binding affinity to nACh alpha4beta2 receptor (unknown origin) assessed as inhib... 37145921
Neuronal acetylcholine receptor; alpha4/beta2 Ki = 0.05 nM 10.3 Binding affinity to alpha4beta2 nAChR in rat brain 23092294
Neuronal acetylcholine receptor; alpha4/beta2 Ki = 0.05 nM 10.3 Displacement of [3H]epibatidine from rat alpha4beta2 nACHR 22148173
Neuronal acetylcholine receptor; alpha4/beta2 Ki = 0.05 nM 10.3 Binding affinity against human Nicotinic acetylcholine receptor alpha4-beta2 10377231
Neuronal acetylcholine receptor Ki = 0.05 nM 10.3 Binding affinity towards nicotinic acetylcholine receptor using [3H]nicotine as ... 12113825
Neuronal acetylcholine receptor; alpha4/beta2 Ki = 0.052 nM 10.28 Agonist activity at alpha4beta2 nAChR (unknown origin) 24814197
Neuronal acetylcholine receptor; alpha4/beta2 Ki = 0.052 nM 10.28 Binding affinity towards Nicotinic acetylcholine receptor alpha4-beta2 in rat br... 9873625
Neuronal acetylcholine receptor Ki = 0.052 nM 10.28 Binding affinity against Nicotinic Acetylcholine Receptor was determined by meas... 8632405
Neuronal acetylcholine receptor; alpha2/beta2 Ki = 0.074 nM 10.13 Binding affinity towards rat nicotinic acetylcholine receptor alpha2-beta2 expre... 15050613
Neuronal acetylcholine receptor; alpha4/beta2 Ki = 0.14 nM 9.85 Binding affinity towards rat Nicotinic acetylcholine receptor alpha4-beta2 expre... 15050613
Neuronal acetylcholine receptor Ki = 0.22 nM 9.66 Binding affinity towards rat forebrain nicotinic acetylcholine receptor using [3... 15050613
Neuronal acetylcholine receptor; alpha3/beta2 Ki = 0.24 nM 9.62 Binding affinity towards rat Nicotinic acetylcholine receptor alpha3-beta2 expre... 15050613
Neuronal acetylcholine receptor Ki = 0.52 nM 9.28 Compound was evaluated for its ability to displace [3H]-cytisine binding from hi... 9484491

Literature References

PubMed DOI Target Context # Activities
15050613 10.1016/j.bmcl.2003.09.105 Unchecked 5
24901260 10.1021/jm401937a Unchecked 5
19301898 10.1021/jm801060h Neuronal acetylcholine receptor; alpha4/beta2 3
23092294 10.1021/jm301177j Neuronal acetylcholine receptor; alpha4/beta2 3
9484491 10.1021/jm9706224 Neuronal acetylcholine receptor subunit alpha-7 2
9484491 10.1021/jm9706224 Neuronal acetylcholine receptor subunit alpha-3 2
8632405 10.1021/jm9506884 IMR-32 2
8632405 10.1021/jm9506884 K177 cell line 2
23092294 10.1021/jm301177j Neuronal acetylcholine receptor subunit alpha-7 2
15050613 10.1016/j.bmcl.2003.09.105 Neuronal acetylcholine receptor; alpha4/beta2 1
9484491 10.1021/jm9706224 Neuronal acetylcholine receptor 1
12113825 10.1016/s0960-894x(02)00298-6 Neuronal acetylcholine receptor 1
15050613 10.1016/j.bmcl.2003.09.105 Neuronal acetylcholine receptor 1
15050613 10.1016/j.bmcl.2003.09.105 Neuronal acetylcholine receptor; alpha4/beta4 1
15050613 10.1016/j.bmcl.2003.09.105 Neuronal acetylcholine receptor; alpha3/beta2 1
15050613 10.1016/j.bmcl.2003.09.105 Neuronal acetylcholine receptor; alpha2/beta2 1
10841800 10.1021/jm990973d Neuronal acetylcholine receptor; alpha4/beta2 1
9435889 10.1021/jm970377o Rattus norvegicus 1
37145921 10.1021/acs.jmedchem.2c01965 Neuronal acetylcholine receptor; alpha4/beta2 1
9435889 10.1021/jm970377o Neuronal acetylcholine receptor subunit alpha-7 1

Data from ChEMBL 36 via Core Engine