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Compound Detail

CHEMBL538700

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Cc1cc(O)cc(C)c1C[C@H](N)C(=O)N1Cc2ccccc2C[C@H]1C(=O)N[C@@H](Cc1ccccc1)C(=O)N[C@@H](Cc1ccccc1)C(N)=O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL538700
Phase Preclinical
Structure Type BOTH
InChI Key KYXSQGDWDGTJNF-BBACVFHCSA-N
7
Targets
11
Activities
3
Assay Types
8
PK Parameters
19
Publications
0
Known Names

Molecular Properties

661.8
MW (Da)
2.77
ALogP
6
HBA
5
HBD
167.8
PSA (Ų)
0.16
QED
1
Ro5 Violations
12
Rot. Bonds

Drug Information

Molecule Type Protein
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C39H43N5O5
MW 661.80
Aromatic Rings 4
Heavy Atoms 49
NP-Likeness -0.12

Activity Summary

Ki 7 meas. best 9.93
IC50 3 meas. best 7.75
Kd 1 meas. best 9.68

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Delta-type opioid receptor
CHEMBL269
 Ki 9.93 9.93 0.1 2
Delta-type opioid receptor
CHEMBL236
 Ki 9.92 9.92 0.1 1
Delta-type opioid receptor
CHEMBL3222
 Kd 9.68 9.68 0.2 1
Mu-type opioid receptor
CHEMBL233
 Ki 8.92 8.92 1.2 1
Mu-type opioid receptor
CHEMBL270
 Ki 8.92 8.92 1.2 3
Mu-type opioid receptor
CHEMBL4354
 IC50 7.75 7.745 18.0 2
Cavia porcellus
CHEMBL369
 IC50 7.74 7.74 18.2 1

Pharmacokinetic Data

Parameter Value Units Species
Ke 0.209 nM Mus musculus
Ke 0.26 nM Mus musculus
Ke 18.0 nM Cavia porcellus
Ke 0.21 nM Mus musculus
Ke 0.21 nM Homo sapiens
Ke 0.21 nM Mus musculus
Ke 0.209 nM Mus musculus
T1/2 0.1017 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Delta-type opioid receptor Ki = 0.118 nM 9.93 Binding affinity for Opioid receptor delta 1 determined by displacing [3H]-DSLET... 10479285
Delta-type opioid receptor Ki = 0.118 nM 9.93 Displacement of [3H]DSLET from delta opioid receptor in rat brain membranes 23932788
Delta-type opioid receptor Ki = 0.12 nM 9.92 Displacement of [3H]DPDPE from human delta opioid receptor expressed in human/mo... 24648867
Delta-type opioid receptor Kd = 0.2089 nM 9.68 Antagonist activity against delta opioid receptor in mouse vas deferens assessed... 19642675
Mu-type opioid receptor Ki = 1.19 nM 8.92 Binding affinity for Opioid receptor mu 1 determined by displacing [3H]DAMGO fro... 10479285
Mu-type opioid receptor Ki = 1.2 nM 8.92 Displacement of [3H]DAMGO from rat mu opioid receptor expressed in human/mouse H... 24648867
Mu-type opioid receptor Ki = 1.19 nM 8.92 Displacement of [3H]DAMGO from mu opioid receptor in rat brain membranes 23932788
Mu-type opioid receptor Ki = 1.19 nM 8.92 Binding affinity at mu opioid receptor (unknown origin) 26656913
Mu-type opioid receptor IC50 = 18.0 nM 7.75 Agonist activity at mu opioid receptor in Hartley guinea pig ileum assessed as i... 24648867
Cavia porcellus IC50 = 18.2 nM 7.74 Compound was evaluated for inhibition of electrically evoked contractions of the... 10479285
Mu-type opioid receptor IC50 = 18.2 nM 7.74 Agonist activity at mu opioid receptor in guinea pig ileum assessed as induction... 23932788

Literature References

PubMed DOI Target Context # Activities
10479285 10.1021/jm980724+ Mu-type opioid receptor 3
24648867 10.1021/ml400115n Delta-type opioid receptor 3
10479285 10.1021/jm980724+ Mus musculus 2
23932788 10.1016/j.bmcl.2013.07.036 Unchecked 2
23932788 10.1016/j.bmcl.2013.07.036 Delta-type opioid receptor 2
23932788 10.1016/j.bmcl.2013.07.036 Mu-type opioid receptor 2
24648867 10.1021/ml400115n Mu-type opioid receptor 2
10479285 10.1021/jm980724+ Delta-type opioid receptor 2
17228874 10.1021/jm060721u Delta-type opioid receptor 1
19642675 10.1021/jm900686q Delta-type opioid receptor 1
17228874 10.1021/jm060721u Mu-type opioid receptor 1
10479285 10.1021/jm980724+ Kappa-type opioid receptor 1
24648867 10.1021/ml400115n Unchecked 1
10479285 10.1021/jm980724+ Rattus norvegicus 1
23932788 10.1016/j.bmcl.2013.07.036 mu/kappa opioid receptor 1
10479285 10.1021/jm980724+ Cavia porcellus 1
23932788 10.1016/j.bmcl.2013.07.036 Kappa-type opioid receptor 1
26656913 10.1016/j.ejmech.2015.11.028 Mu-type opioid receptor 1
34995453 10.1021/acs.jmedchem.0c01915 ADMET 1

Data from ChEMBL 36 via Core Engine