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Compound Detail

CHEMBL2181202

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

Basic Information

ChEMBL ID CHEMBL2181202
Phase Preclinical
Structure Type BOTH
InChI Key FIAKHZXVLBNZLW-NFGXINMFSA-N
12
Targets
32
Activities
2
Assay Types
2
PK Parameters
20
Publications
0
Known Names

Molecular Properties

639.8
MW (Da)
-0.55
ALogP
8
HBA
10
HBD
264.6
PSA (Ų)
0.05
QED
2
Ro5 Violations
19
Rot. Bonds

Drug Information

Molecule Type Protein
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C32H49N9O5
MW 639.80
Aromatic Rings 2
Heavy Atoms 46
NP-Likeness 0.34

Activity Summary

Ki 19 meas. best 9.85
IC50 13 meas. best 8.85

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Mu-type opioid receptor
CHEMBL233
 Ki 9.85 9.85 0.1 2
Mu-type opioid receptor
CHEMBL270
 Ki 9.85 9.6975 0.1 4
Mu-type opioid receptor
CHEMBL3041
 Ki 9.85 9.85 0.1 1
Unchecked
CHEMBL612545
 Ki 9.85 7.49 0.1 3
Mu-type opioid receptor
CHEMBL4354
 IC50 8.85 8.85 1.4 7
Kappa-type opioid receptor
CHEMBL4329
 Ki 7.94 7.94 11.5 1
Kappa-type opioid receptor
CHEMBL3952
 Ki 7.65 7.65 22.3 2
Mu-type opioid receptor
CHEMBL2858
 IC50 7.64 7.64 23.1 1
Delta-type opioid receptor
CHEMBL3222
 IC50 7.64 7.64 23.1 5
Delta-type opioid receptor
CHEMBL269
 Ki 6.06 5.775 877.0 4
Delta-type opioid receptor
CHEMBL236
 Ki 5.68 5.68 2100.0 1
Kappa-type opioid receptor
CHEMBL237
 Ki 5.62 5.62 2407.0 1

Pharmacokinetic Data

Parameter Value Units Species
T1/2 1.8 hr Ovis aries
Vz 19.25 uL/g Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Mu-type opioid receptor Ki = 0.14 nM 9.85 Displacement of [3H]DAMGO from calf thalamus membrane MOP by competitive binding... 34995453
Mu-type opioid receptor Ki = 0.143 nM 9.85 Displacement of [3H]DAMGO from mu-type opioid receptor in rat brain membranes in... 27301366
Mu-type opioid receptor Ki = 0.143 nM 9.85 Binding affinity at mu opioid receptor (unknown origin) 26656913
Mu-type opioid receptor Ki = 0.143 nM 9.85 Displacement of [3H]DAMGO from mu opioid receptor in rat brain membranes 24839540
Mu-type opioid receptor Ki = 0.143 nM 9.85 Binding affinity to mu opioid receptor 23102273
Mu-type opioid receptor Ki = 0.143 nM 9.85 Displacement of [3H]DAMGO from mu opioid receptor in rat brain membranes after 2... 23102273
Unchecked Ki = 0.143 nM 9.85 Inhibition constant against synaptosomal Mu opioid receptor 16107162
Mu-type opioid receptor Ki = 0.58 nM 9.24 Displacement of [3H]DAMGO from mu opioid receptor in rat brain membrane after 2 ... 26713106
Mu-type opioid receptor IC50 = 1.41 nM 8.85 Agonist activity at mu opioid receptor in guinea pig ileum 23102273
Mu-type opioid receptor IC50 = 1.41 nM 8.85 Agonist activity against mu opioid receptor of guinea pig ileum 16107162
Mu-type opioid receptor IC50 = 1.41 nM 8.85 Agonist activity at mu opioid receptor in guinea pig ileum 24839540
Mu-type opioid receptor IC50 = 1.41 nM 8.85 Antagonist activity at guinea pig ileum MOP 34995453
Mu-type opioid receptor IC50 = 1.41 nM 8.85 Agonist activity at mu opioid receptor in guinea pig ileum assessed as inhibitio... 27301366
Mu-type opioid receptor IC50 = 1.41 nM 8.85 Agonist activity at mu opioid receptor in guinea pig ileum assessed as inhibitio... 26713106
Mu-type opioid receptor IC50 = 1.41 nM 8.85 Agonist activity at mu-opioid receptor in guinea pig ileum 26656913
Kappa-type opioid receptor Ki = 11.5 nM 7.94 Displacement of [3H]U69593 from mouse brain membrane KOP by competitive binding ... 34995453
Kappa-type opioid receptor Ki = 22.3 nM 7.65 Displacement of [3H]U69,593 from kappa-type opioid receptor in guniea pig brain ... 27301366
Kappa-type opioid receptor Ki = 22.3 nM 7.65 Displacement of [3H]U69,593 from kappa opioid receptor in guinea pig ileum membr... 23102273
Delta-type opioid receptor IC50 = 23.1 nM 7.64 Agonist activity at delta opioid receptor in mouse vas deferens assessed as inhi... 26713106
Delta-type opioid receptor IC50 = 23.1 nM 7.64 Agonistic activity against delta opioid receptor of mouse vas deferens assay 16107162

Literature References

PubMed DOI Target Context # Activities
24839540 10.1021/ml4004765 Mus musculus 10
23102273 10.1021/jm3008079 Mus musculus 7
23102273 10.1021/jm3008079 Brain 6
24839540 10.1021/ml4004765 Caco-2 4
34995453 10.1021/acs.jmedchem.0c01915 Mus musculus 4
23102273 10.1021/jm3008079 Mu-type opioid receptor 4
34995453 10.1021/acs.jmedchem.0c01915 Mu-type opioid receptor 3
27301366 10.1016/j.bmcl.2016.06.003 Rattus norvegicus 3
27301366 10.1016/j.bmcl.2016.06.003 Mu-type opioid receptor 2
23102273 10.1021/jm3008079 Delta-type opioid receptor 2
23102273 10.1021/jm3008079 Plasma 2
23102273 10.1021/jm3008079 Unchecked 2
27301366 10.1016/j.bmcl.2016.06.003 Delta-type opioid receptor 2
27301366 10.1016/j.bmcl.2016.06.003 Unchecked 2
24839540 10.1021/ml4004765 Mu-type opioid receptor 2
24839540 10.1021/ml4004765 Delta-type opioid receptor 2
26713106 10.1021/acsmedchemlett.5b00359 Delta-type opioid receptor 2
26713106 10.1021/acsmedchemlett.5b00359 Mu-type opioid receptor 2
16107162 10.1021/jm0504959 Unchecked 2
26656913 10.1016/j.ejmech.2015.11.028 Mu-type opioid receptor 2

Data from ChEMBL 36 via Core Engine