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Compound Detail

CHEMBL440765

U-69593
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CN(C(=O)Cc1ccccc1)[C@H]1CC[C@@]2(CCCO2)C[C@@H]1N1CCCC1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL440765
Name U-69593
Phase Preclinical
Structure Type MOL
InChI Key PGZRDDYTKFZSFR-ONTIZHBOSA-N
15
Targets
134
Activities
4
Assay Types
5
PK Parameters
20
Publications
0
Known Names

Molecular Properties

356.5
MW (Da)
3.25
ALogP
3
HBA
0
HBD
32.8
PSA (Ų)
0.83
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 C22H32N2O2
MW 356.51
Aromatic Rings 1
Heavy Atoms 26
NP-Likeness 0.17

Activity Summary

Ki 58 meas. best 9.52
EC50 45 meas. best 9.49
IC50 21 meas. best 9.2
Kd 10 meas. best 9.0

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Kappa-type opioid receptor
CHEMBL237
 Ki 9.52 8.8625 0.3 16
Kappa-type opioid receptor
CHEMBL237
 EC50 9.49 7.6178 0.3 41
Kappa-type opioid receptor
CHEMBL3614
 IC50 9.2 9.2 0.6 1
Kappa-type opioid receptor
CHEMBL3952
 Ki 9.15 8.8759 0.7 17
Kappa-type opioid receptor
CHEMBL3614
 Kd 9.0 9.0 1.0 1
Mu-type opioid receptor
CHEMBL2858
 Ki 8.93 7.595 1.2 2
Kappa-type opioid receptor
CHEMBL3614
 Ki 8.85 8.555 1.4 6
Unchecked
CHEMBL612545
 Ki 8.7 8.6133 2.0 3
Kappa-type opioid receptor
CHEMBL237
 IC50 8.7 8.42 2.0 4
Kappa-type opioid receptor
CHEMBL3952
 IC50 8.68 8.68 2.1 2
Cavia porcellus
CHEMBL369
 EC50 8.66 8.66 2.2 1
Kappa-type opioid receptor
CHEMBL3952
 Kd 8.37 6.33 4.3 3
Kappa-type opioid receptor
CHEMBL3614
 EC50 8.11 8.11 7.7 1
Mus musculus
CHEMBL375
 EC50 7.55 7.55 28.0 1
Mu-type opioid receptor
CHEMBL4354
 Ki 7.28 6.3575 52.0 4
Opioid receptors; mu/kappa/delta
CHEMBL2095181
 IC50 6.86 6.86 139.0 1
Unchecked
CHEMBL612545
 IC50 6.85 6.85 140.0 1
Mu-type opioid receptor
CHEMBL233
 IC50 6.61 6.605 248.0 2
Delta-type opioid receptor
CHEMBL3222
 Ki 6.41 6.41 391.0 1
Mu-type opioid receptor
CHEMBL4354
 Kd 6.17 5.92 684.0 4
Nociceptin receptor
CHEMBL5492
 Ki 5.96 5.96 1099.0 1
Mu-type opioid receptor
CHEMBL233
 Ki 5.94 5.78 1145.0 4
Delta-type opioid receptor
CHEMBL236
 Ki 5.87 5.2233 1358.0 3
Kappa-type opioid receptor
CHEMBL3952
 EC50 5.84 5.84 1445.4 1
Mu-type opioid receptor
CHEMBL4354
 IC50 5.75 5.75 1760.0 2
Delta-type opioid receptor
CHEMBL236
 Kd 5.7 5.7 1980.0 2
Delta-type opioid receptor
CHEMBL236
 IC50 5.3 5.2675 4970.0 4
Mu-type opioid receptor
CHEMBL270
 Ki 5.14 5.14 7250.0 1
Plasmodium falciparum
CHEMBL364
 IC50 5.1 4.975 7943.3 4

Pharmacokinetic Data

Parameter Value Units Species
Ke 9.0 nM Cavia porcellus
Ke 20.4 nM Mus musculus
Ke - - Homo sapiens
Ke - - Homo sapiens
Ke - - Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Kappa-type opioid receptor Ki = 0.3 nM 9.52 Displacement of [3H]U-69593 from human recombinant Opioid receptor kappa 1 on CH... 12672258
Kappa-type opioid receptor Ki = 0.3 nM 9.52 Displacement of [3H]U69,593 from human kappa opioid receptor expressed in CHO ce... 23134120
Kappa-type opioid receptor Ki = 0.3 nM 9.52 Binding affinity to KOR (unknown origin) assessed as inhibition constant 36179400
Kappa-type opioid receptor EC50 = 0.32 nM 9.49 Agonist activity at KOR (unknown origin) by measuring cAMP inhibition 36179400
Kappa-type opioid receptor Ki = 0.475 nM 9.32 Binding affinity to kappa opioid receptor 20478711
Kappa-type opioid receptor IC50 = 0.63 nM 9.2 Binding affinity against rat kappa-opioid receptor expressed in CHO cells was de... 9873480
Kappa-type opioid receptor Ki = 0.7 nM 9.15 Displacement of radiolabeled U69593 from kappa1 opioid receptor in Hartley guine... 16777416
Kappa-type opioid receptor Ki = 0.73 nM 9.14 Inhibition of KOR in guinea pig brain membrane by liquid scintillation counter a... 37678143
Kappa-type opioid receptor EC50 = 0.8 nM 9.1 Agonist activity at human KOR expressed in CHO cells assessed as inhibition of f... 25426797
Kappa-type opioid receptor Ki = 0.88 nM 9.06 Displacement of [3H]U-69593 from kappa-opioid receptor in guinea pig brain membr... 24856182
Kappa-type opioid receptor Ki = 0.97 nM 9.01 Displacement of [3H]U69593 from kappa opioid receptor in guinea pig brain membra... 20441176
Kappa-type opioid receptor Ki = 0.97 nM 9.01 Displacement of [3H]U-69593 from kappa opioid receptor in guinea pig brain membr... 25062506
Kappa-type opioid receptor Ki = 0.97 nM 9.01 Displacement of [3H]U-69,593 from kappa opioid receptor in guinea pig brain memb... -
Kappa-type opioid receptor Ki = 0.97 nM 9.01 Displacement of [3H]U-69,593 from kappa-type opioid receptor in guinea pig brain... 28218838
Kappa-type opioid receptor Ki = 0.97 nM 9.01 Displacement of [3H]U-69,593 from kappa opioid receptor in guinea pig brain memb... -
Kappa-type opioid receptor Ki = 0.97 nM 9.01 Displacement of [3H]U-69,593 from KOR in guinea pig brain membranes after 120 mi... 30543421
Kappa-type opioid receptor Kd = 1.0 nM 9.0 Binding affinity to rat kappa opioid receptor expressed in HEK293 cell membranes 25593096
Kappa-type opioid receptor Ki = 1.05 nM 8.98 Displacement of [3H]U69,593 from human kappa opioid receptor transfected in CHO ... 24657054
Kappa-type opioid receptor Ki = 1.06 nM 8.97 Tested for inhibitory effect on binding of [3H]bremazocine to opioid receptor ka... 1361580
Kappa-type opioid receptor Ki = 1.11 nM 8.96 Binding affinity against opioid receptor kappa 1 from human cloned receptor 12930147

Literature References

PubMed DOI Target Context # Activities
10753461 10.1021/jm990583r Kappa-type opioid receptor 5
11300879 10.1021/jm000427g Mu-type opioid receptor 4
19734910 10.1038/nchembio.215 Plasmodium falciparum 4
10571174 10.1016/s0960-894x(99)00525-9 Mu-type opioid receptor 4
10612597 10.1016/s0960-894x(99)00613-7 Mu-type opioid receptor 4
17904842 10.1016/j.bmcl.2007.09.050 Kappa-type opioid receptor 4
16441078 10.1021/np050398i Kappa-type opioid receptor 4
34465090 10.1021/acs.jmedchem.1c00694 Kappa-type opioid receptor 3
12672258 10.1021/jm021073r Delta-type opioid receptor 3
12672258 10.1021/jm021073r Kappa-type opioid receptor 3
25221662 10.1021/ml500241n Kappa-type opioid receptor 3
12672258 10.1021/jm021073r Mu-type opioid receptor 3
23134120 10.1021/jm301258w Kappa-type opioid receptor 3
28218838 10.1021/acs.jmedchem.6b01868 Kappa-type opioid receptor 3
34465090 10.1021/acs.jmedchem.1c00694 Mu-type opioid receptor 3
10753461 10.1021/jm990583r Unchecked 3
29939744 10.1021/acs.jmedchem.8b00435 Kappa-type opioid receptor 3
25147605 10.1021/ml5000542 Kappa-type opioid receptor 3
23200250 10.1016/j.bmcl.2012.10.100 Kappa-type opioid receptor 3
17580847 10.1021/jm070393d Kappa-type opioid receptor 3

Data from ChEMBL 36 via Core Engine