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Compound Detail

CHEMBL571492

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Cc1cc(O)cc(C)c1C[C@H](N)C(=O)N1Cc2ccccc2C[C@H]1C(=O)O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL571492
Phase Preclinical
Structure Type MOL
InChI Key QBLVXTMPLLWZDE-OALUTQOASA-N
7
Targets
22
Activities
3
Assay Types
4
PK Parameters
20
Publications
0
Known Names

Molecular Properties

368.4
MW (Da)
1.92
ALogP
4
HBA
3
HBD
103.9
PSA (Ų)
0.76
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 C21H24N2O4
MW 368.43
Aromatic Rings 2
Heavy Atoms 27
NP-Likeness 0.06

Activity Summary

Ki 16 meas. best 10.66
IC50 3 meas. best 8.8
Kd 3 meas. best 8.5

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Delta-type opioid receptor
CHEMBL269
 Ki 10.66 9.4371 0.0 7
Unchecked
CHEMBL612545
 Ki 10.66 8.075 0.0 2
Delta-type opioid receptor
CHEMBL236
 IC50 8.8 8.8 1.6 1
Delta-type opioid receptor
CHEMBL3222
 Kd 8.5 8.49 3.2 2
Delta-type opioid receptor
CHEMBL269
 Kd 8.48 8.48 3.3 1
Mu-type opioid receptor
CHEMBL270
 Ki 8.48 5.9457 3.3 7
Mu-type opioid receptor
CHEMBL233
 IC50 6.05 6.05 894.0 1
Kappa-type opioid receptor
CHEMBL237
 IC50 4.43 4.43 37503.0 1

Pharmacokinetic Data

Parameter Value Units Species
Ke 5.3 nM -
Ke 6.55 nM Mus musculus
Ke - - Cavia porcellus
Ke 6.55 nM Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Delta-type opioid receptor Ki = 0.022 nM 10.66 Binding affinity for Opioid receptor delta 1 by displacement of [3H]- DPDPE 9301674
Delta-type opioid receptor Ki = 0.022 nM 10.66 Binding affinity at Opioid receptor delta 1 using rat brain receptor (P2 synapto... 11806723
Unchecked Ki = 0.022 nM 10.66 Binding affinity for rat brain opioid receptor delta 1 15664820
Delta-type opioid receptor Ki = 0.022 nM 10.66 Displacement of [3H]deltorphin-II from delta opioid receptor in rat brain synapt... 16335927
Delta-type opioid receptor Ki = 0.222 nM 9.65 Displacement of [3H]deltorphin 2 from delta opioid receptor in rat brain membran... 20137938
Delta-type opioid receptor IC50 = 1.6 nM 8.8 Compound was evaluated for binding affinity towards Opioid receptor delta 1 by d... 10673103
Delta-type opioid receptor Ki = 1.64 nM 8.79 Displacement of [3H]DSLET from delta opioid receptor in rat brain membranes 23932788
Delta-type opioid receptor Ki = 1.84 nM 8.73 Displacement of [3H]DSLET from delta opioid receptor in rat brain membrane 19827750
Delta-type opioid receptor Kd = 3.162 nM 8.5 Displacement of deltorphin-II from delta opioid receptor in mouse vas deferens 16183273
Delta-type opioid receptor Kd = 3.311 nM 8.48 Displacement of deltorphin-II from delta opioid receptor in mouse vas deferens 16335927
Delta-type opioid receptor Kd = 3.311 nM 8.48 Antagonist activity at delta opioid receptor in rat NG108-15 cells assessed as i... 20137938
Mu-type opioid receptor Ki = 3.317 nM 8.48 Displacement of [3H]DAMGO from mu opioid receptor in rat brain membranes 20137938
Delta-type opioid receptor Ki = 123.9 nM 6.91 Binding affinity for Opioid receptor delta 1 by displacement of [3H]- DPDPE 9301674
Mu-type opioid receptor IC50 = 894.0 nM 6.05 Compound was evaluated for binding affinity towards Opioid receptor mu 1 by disp... 10673103
Mu-type opioid receptor Ki = 1360.0 nM 5.87 Displacement of [3H]DAMGO from mu opioid receptor in rat brain membrane 19827750
Mu-type opioid receptor Ki = 1360.0 nM 5.87 Displacement of [3H]DAMGO from mu opioid receptor in rat brain membranes 23932788
Unchecked Ki = 3220.0 nM 5.49 Binding affinity for rat brain opioid receptor mu 1 15664820
Mu-type opioid receptor Ki = 3320.0 nM 5.48 Binding affinity for Opioid receptor mu 1 by displacement of [3H]- DAGO 9301674
Mu-type opioid receptor Ki = 3320.0 nM 5.48 Binding affinity for rat brain P2 synaptosome Opioid receptor mu 1 11806723
Mu-type opioid receptor Ki = 3320.0 nM 5.48 Displacement of [3H]DAMGO from mu opioid receptor expressed in rat brain synapto... 16335927

Literature References

PubMed DOI Target Context # Activities
9301674 10.1021/jm9607663 Mu-type opioid receptor 6
9301674 10.1021/jm9607663 Delta-type opioid receptor 5
19827750 10.1021/jm9004913 Mu-type opioid receptor 3
16335927 10.1021/jm050377l Mu-type opioid receptor 3
15664820 10.1016/j.bmcl.2004.11.040 Unchecked 3
23932788 10.1016/j.bmcl.2013.07.036 Delta-type opioid receptor 2
23932788 10.1016/j.bmcl.2013.07.036 Unchecked 2
20137938 10.1016/j.bmcl.2010.01.055 Delta-type opioid receptor 2
19827750 10.1021/jm9004913 Unchecked 2
19827750 10.1021/jm9004913 Delta-type opioid receptor 2
16335927 10.1021/jm050377l Delta-type opioid receptor 2
10673103 10.1016/s0960-894x(99)00652-6 Delta-type opioid receptor 2
11806723 10.1021/jm010449i Delta-type opioid receptor 2
9301674 10.1021/jm9607663 Opioid receptors; mu & delta 2
10673103 10.1016/s0960-894x(99)00652-6 Opioid receptors; mu & delta 1
23932788 10.1016/j.bmcl.2013.07.036 Mu-type opioid receptor 1
10673103 10.1016/s0960-894x(99)00652-6 Kappa-type opioid receptor 1
10673103 10.1016/s0960-894x(99)00652-6 Mu-type opioid receptor 1
19827750 10.1021/jm9004913 Kappa-type opioid receptor 1
20137938 10.1016/j.bmcl.2010.01.055 Mu-type opioid receptor 1

Data from ChEMBL 36 via Core Engine