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Compound Detail

CHEMBL331325

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Cc1cc(O)cc(C)c1C[C@H](N)C(=O)N1CCC[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 CHEMBL331325
Phase Preclinical
Structure Type BOTH
InChI Key PJAMNQXPYIKTPE-KRCBVYEFSA-N
10
Targets
15
Activities
3
Assay Types
2
PK Parameters
19
Publications
0
Known Names

Molecular Properties

599.7
MW (Da)
1.81
ALogP
6
HBA
5
HBD
167.8
PSA (Ų)
0.21
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 C34H41N5O5
MW 599.73
Aromatic Rings 3
Heavy Atoms 44
NP-Likeness -0.11

Activity Summary

Ki 9 meas. best 9.82
IC50 4 meas. best 10.15
EC50 2 meas. best 10.0

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Cavia porcellus
CHEMBL369
 IC50 10.15 10.15 0.1 1
Mu-type opioid receptor
CHEMBL233
 EC50 10.0 9.39 0.1 2
Mu-type opioid receptor
CHEMBL270
 Ki 9.82 9.6967 0.1 3
Mu-type opioid receptor
CHEMBL4354
 IC50 9.59 9.59 0.3 1
Delta-type opioid receptor
CHEMBL3222
 IC50 9.23 9.23 0.6 1
Mu-type opioid receptor
CHEMBL233
 Ki 9.09 9.09 0.8 1
Mus musculus
CHEMBL375
 IC50 8.73 8.73 1.9 1
Delta-type opioid receptor
CHEMBL269
 Ki 7.55 7.275 28.2 2
Delta-type opioid receptor
CHEMBL236
 Ki 6.55 6.55 283.0 1
Kappa-type opioid receptor
CHEMBL3952
 Ki 6.31 6.31 489.0 1
Kappa-type opioid receptor
CHEMBL237
 Ki 6.28 6.28 520.0 1

Pharmacokinetic Data

Parameter Value Units Species
T1/2 0.6592 hr Rattus norvegicus
T1/2 0.8833 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Cavia porcellus IC50 = 0.07 nM 10.15 In vitro inhibitory concentration against electrically induced twitches in guine... 15214786
Mu-type opioid receptor EC50 = 0.1 nM 10.0 Agonist activity at human MOR expressed in CHO cell membranes after 60 mins by [... 30351003
Mu-type opioid receptor Ki = 0.15 nM 9.82 Binding affinity against rat brain Opioid receptor mu 1 using [3H]DAMGO radiolig... 15214786
Mu-type opioid receptor Ki = 0.21 nM 9.68 Inhibition of DAMGO (Tyr-[D-Ala]-Gly-[NMe-Phe]-Gly-ol) binding to rat brain mu o... 15857130
Mu-type opioid receptor IC50 = 0.26 nM 9.59 Agonist activity at mu opioid receptor in Hartley guinea pig ileum assessed as i... 17497839
Mu-type opioid receptor Ki = 0.26 nM 9.59 Displacement of [3H]DAMGO from mu opioid receptor in Sprague-Dawley rat brain P2... 17497839
Delta-type opioid receptor IC50 = 0.59 nM 9.23 Agonist activity at delta opioid receptor in mouse vas deferens assessed as inhi... 17497839
Mu-type opioid receptor Ki = 0.81 nM 9.09 Displacement of [3H]DAMGO from human recombinant MOR expressed in CHO cell membr... 31276897
Mu-type opioid receptor EC50 = 1.66 nM 8.78 Agonist activity at human recombinant MOR expressed in CHO cells co-expressing C... 31276897
Mus musculus IC50 = 1.87 nM 8.73 In vitro inhibitory concentration against electrically induced twitches in mouse... 15214786
Delta-type opioid receptor Ki = 28.2 nM 7.55 Binding affinity against rat brain opioid receptor delta 1 using [3H]DPDPE radio... 15214786
Delta-type opioid receptor Ki = 99.2 nM 7.0 Displacement of [3H]deltorphin 2 from delta opioid receptor in Sprague-Dawley ra... 17497839
Delta-type opioid receptor Ki = 283.0 nM 6.55 Displacement of [3H]deltrophin-2 from human recombinant DOR expressed in CHO cel... 31276897
Kappa-type opioid receptor Ki = 489.0 nM 6.31 Displacement of [3H]U-69593 from kappa opioid receptor in Hartley guinea pig cer... 17497839
Kappa-type opioid receptor Ki = 520.0 nM 6.28 Displacement of [3H]U-69593 from human recombinant KOR expressed in CHO cell mem... 31276897

Literature References

PubMed DOI Target Context # Activities
31276897 10.1016/j.ejmech.2019.06.077 Mu-type opioid receptor 4
31276897 10.1016/j.ejmech.2019.06.077 No relevant target 2
17497839 10.1021/jm061238m Mu-type opioid receptor 2
17497839 10.1021/jm061238m Delta-type opioid receptor 2
30351003 10.1021/acs.jmedchem.8b01282 Mu-type opioid receptor 2
17497839 10.1021/jm061238m Kappa-type opioid receptor 1
31276897 10.1016/j.ejmech.2019.06.077 Kappa-type opioid receptor 1
31276897 10.1016/j.ejmech.2019.06.077 Delta-type opioid receptor 1
30351003 10.1021/acs.jmedchem.8b01282 Mus musculus 1
24839540 10.1021/ml4004765 Plasma 1
24839540 10.1021/ml4004765 Brain 1
17497839 10.1021/jm061238m Opioid receptor (mu and kappa) 1
15214786 10.1021/jm030649p Mu-type opioid receptor 1
17497839 10.1021/jm061238m Opioid receptors; mu & delta 1
15857130 10.1021/jm049157i Mu-type opioid receptor 1
15214786 10.1021/jm030649p Mus musculus 1
15214786 10.1021/jm030649p Cavia porcellus 1
15214786 10.1021/jm030649p Opioid receptors; mu & delta 1
15214786 10.1021/jm030649p Delta-type opioid receptor 1

Data from ChEMBL 36 via Core Engine