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Compound Detail

CHEMBL290543

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CN(C(=O)Cc1ccc(Cl)c(Cl)c1)C1CCCCC1N1CCCC1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL290543
Phase Preclinical
Structure Type MOL
InChI Key VQLPLYSROCPWFF-UHFFFAOYSA-N
16
Targets
162
Activities
3
Assay Types
8
PK Parameters
20
Publications
0
Known Names

Molecular Properties

369.3
MW (Da)
4.40
ALogP
2
HBA
0
HBD
23.6
PSA (Ų)
0.79
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C19H26Cl2N2O
MW 369.34
Aromatic Rings 1
Heavy Atoms 24
NP-Likeness -0.64

Activity Summary

Ki 91 meas. best 10.03
EC50 40 meas. best 9.27
IC50 31 meas. best 9.52

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Kappa-type opioid receptor
CHEMBL237
 Ki 10.03 8.7429 0.1 31
Mus musculus
CHEMBL375
 Ki 9.82 9.31 0.1 3
Kappa-type opioid receptor
CHEMBL3952
 Ki 9.57 8.6234 0.3 32
Kappa-type opioid receptor
CHEMBL237
 IC50 9.52 8.7243 0.3 14
Kappa-type opioid receptor
CHEMBL3952
 IC50 9.52 8.29 0.3 5
Kappa-type opioid receptor
CHEMBL3614
 Ki 9.35 9.285 0.5 2
Kappa-type opioid receptor
CHEMBL237
 EC50 9.27 7.892 0.5 35
Kappa-type opioid receptor
CHEMBL3614
 IC50 9.19 9.18 0.6 2
Kappa-type opioid receptor
CHEMBL4329
 IC50 8.9 8.655 1.3 4
Kappa-type opioid receptor
CHEMBL4329
 EC50 8.77 7.2467 1.7 3
Cavia porcellus
CHEMBL369
 IC50 8.66 8.66 2.2 1
Opioid receptors; mu/kappa/delta
CHEMBL2095181
 IC50 8.58 8.58 2.6 1
Opioid receptors; mu & kappa
CHEMBL2095156
 IC50 8.3 6.905 5.0 2
Kappa-type opioid receptor
CHEMBL4329
 Ki 8.09 8.09 8.1 1
Mu-type opioid receptor
CHEMBL4354
 Ki 6.69 6.3156 206.0 9
Mu-type opioid receptor
CHEMBL233
 Ki 6.54 6.35 290.0 3
Sigma non-opioid intracellular receptor 1
CHEMBL287
 Ki 6.16 6.04 696.0 3
Mu-type opioid receptor
CHEMBL270
 Ki 6.14 5.8567 716.0 3
c-Jun N-terminal kinase, JNK
CHEMBL2096667
 EC50 5.91 5.91 1240.0 1
Opioid receptor
CHEMBL2094129
 IC50 5.67 5.295 2150.0 2
Delta-type opioid receptor
CHEMBL236
 Ki 5.6 5.2933 2500.0 3
Mu-type opioid receptor
CHEMBL233
 EC50 5.32 5.32 4840.0 1
Delta-type opioid receptor
CHEMBL269
 Ki 5.09 5.09 8100.0 1

Pharmacokinetic Data

Parameter Value Units Species
Ke 12.3 nM -
Ke 15.5 nM Mus musculus
Ke 0.031 nM Cavia porcellus
Ke 12.1 nM Cavia porcellus
Ke 0.031 nM Mus musculus
Ke 31.5 nM Mus musculus
Ke 41.2 nM Mus musculus
Ke - - Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Kappa-type opioid receptor Ki = 0.094 nM 10.03 Displacement of [3H]-U69593 from human kappa opioid receptor expressed in U2OS c... 33326237
Kappa-type opioid receptor Ki = 0.1 nM 10.0 Displacement of [3H]-U69593 from human kappa opioid receptor expressed in U2OS c... 33326237
Mus musculus Ki = 0.15 nM 9.82 Antinociceptive activity determined in vivo in tail flick assay in male Swiss mi... 8390575
Kappa-type opioid receptor Ki = 0.2 nM 9.7 Displacement of [3H]U69,593 from human kappa opioid receptor expressed in CHO ce... 23134120
Kappa-type opioid receptor Ki = 0.27 nM 9.57 Displacement of [3H]-U69,593 from KOR in guinea pig brain membranes incubated fo... 32435370
Kappa-type opioid receptor IC50 = 0.3 nM 9.52 Agonist activity at recombinant human KOR expressed in HEK293T cells assessed as... 28726402
Kappa-type opioid receptor IC50 = 0.3 nM 9.52 Agonist activity at human kappa opioid receptor expressed in HEK293 cells assess... 25087049
Kappa-type opioid receptor IC50 = 0.303 nM 9.52 Displacement of [3H]U69,593 from kappa opioid receptor in guinea pig cerebellum 18990576
Kappa-type opioid receptor Ki = 0.3 nM 9.52 Displacement of [3H]U69,593 from human recombinant kappa opioid receptor express... 31834797
Kappa-type opioid receptor Ki = 0.31 nM 9.51 Displacement of [3H]U69593 from kappa opioid receptor in guinea pig brain membra... 20441176
Kappa-type opioid receptor Ki = 0.31 nM 9.51 Displacement of [3H]U69593 from kappa opioid receptor in guinea pig brain membra... 21481987
Kappa-type opioid receptor Ki = 0.3162 nM 9.5 Displacement of [3H]-U69593 from kappa opioid receptor (unknown origin) assessed... 36827198
Kappa-type opioid receptor Ki = 0.34 nM 9.47 Displacement of [3H]-U69,593 from KOR in guinea pig brain membranes incubated fo... 30822708
Kappa-type opioid receptor Ki = 0.34 nM 9.47 Displacement of [3H]U-69593 from kappa opioid receptor in guinea pig brain membr... 25062506
Kappa-type opioid receptor Ki = 0.34 nM 9.47 Displacement of [3H]U-69593 from kappa-opioid receptor in guinea pig brain membr... 24856182
Kappa-type opioid receptor Ki = 0.34 nM 9.47 Displacement of [3H]BREM from kappa opioid receptor in guinea pig brain membrane... -
Kappa-type opioid receptor Ki = 0.34 nM 9.47 Displacement of [3H]-U69593 from KOR in guinea pig brain membranes measured by c... 35033825
Kappa-type opioid receptor Ki = 0.36 nM 9.44 Binding affinity towards Opioid receptor kappa 1 by displacing the radioligand [... 10633042
Kappa-type opioid receptor Ki = 0.36 nM 9.44 Binding affinity towards Opioid receptor kappa 1 in guinea pig brain membranes u... 11591513
Kappa-type opioid receptor Ki = 0.45 nM 9.35 Displacement of [3H]U 69593 from rat recombinant kappa opioid receptor expressed... 27997171

Literature References

PubMed DOI Target Context # Activities
6128415 10.1021/jm00352a005 Mus musculus 6
33326237 10.1021/acs.jnatprod.0c01036 Kappa-type opioid receptor 5
34308635 10.1021/acs.jnatprod.1c00301 Kappa-type opioid receptor 5
8390575 10.1021/jm00065a009 Mus musculus 4
18829333 10.1016/j.bmc.2008.09.011 Kappa-type opioid receptor 4
19091564 10.1016/j.bmcl.2008.11.076 Kappa-type opioid receptor 4
19027293 10.1016/j.bmcl.2008.10.134 Kappa-type opioid receptor 4
25996309 10.1021/jm501637c Mus musculus 4
15771416 10.1021/jm034234f Mus musculus 4
1319495 10.1021/jm00090a015 Kappa-type opioid receptor 4
22204910 10.1016/j.bmcl.2011.11.128 Kappa-type opioid receptor 4
16942039 10.1021/jm060278n Kappa-type opioid receptor 4
1319495 10.1021/jm00090a015 Mu-type opioid receptor 4
38810170 10.1021/acs.jmedchem.4c00333 Kappa-type opioid receptor 4
17702750 10.1074/jbc.m705540200 c-Jun N-terminal kinase, JNK 3
16777411 10.1016/j.bmcl.2006.05.093 Kappa-type opioid receptor 3
1846918 10.1021/jm00105a027 Mus musculus 3
17276685 10.1016/j.bmcl.2007.01.013 Kappa-type opioid receptor 3
17433695 10.1016/j.bmc.2007.03.076 Kappa-type opioid receptor 3
1652025 10.1021/jm00112a042 Mus musculus 3

Data from ChEMBL 36 via Core Engine