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Compound Detail

CHEMBL2322568

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Cc1cc(O)cc(C)c1C[C@H](N)C(=O)N[C@@H]1CCNc2ccc(Cc3ccccc3)cc21
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL2322568
Phase Preclinical
Structure Type MOL
InChI Key VTFUYBNMSGPAQU-AZGAKELHSA-N
6
Targets
15
Activities
2
Assay Types
1
PK Parameters
15
Publications
0
Known Names

Molecular Properties

429.6
MW (Da)
4.14
ALogP
4
HBA
4
HBD
87.4
PSA (Ų)
0.47
QED
0
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C27H31N3O2
MW 429.56
Aromatic Rings 3
Heavy Atoms 32
NP-Likeness 0.38

Activity Summary

Ki 9 meas. best 9.66
EC50 6 meas. best 8.8

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Mu-type opioid receptor
CHEMBL270
 Ki 9.66 9.66 0.2 2
Mu-type opioid receptor
CHEMBL4354
 Ki 9.66 9.66 0.2 1
Mu-type opioid receptor
CHEMBL270
 EC50 8.8 8.8 1.6 2
Delta-type opioid receptor
CHEMBL269
 Ki 8.03 8.03 9.4 2
Unchecked
CHEMBL612545
 Ki 8.03 8.03 9.4 1
Kappa-type opioid receptor
CHEMBL237
 Ki 7.17 7.17 68.0 2
Kappa-type opioid receptor
CHEMBL3952
 Ki 7.17 7.17 68.0 1
Delta-type opioid receptor
CHEMBL269
 EC50 6.96 6.96 110.0 2
Kappa-type opioid receptor
CHEMBL237
 EC50 6.27 6.27 540.0 2

Pharmacokinetic Data

Parameter Value Units Species
T1/2 0.05167 hr Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Mu-type opioid receptor Ki = 0.22 nM 9.66 Displacement of [3H]diprenorphine from rat MOR expressed in rat C6 cells after 1... 23419026
Mu-type opioid receptor Ki = 0.22 nM 9.66 Displacement of [3H]diprenorphine from rat mu-opioid receptor expressed in C6 ce... 26524472
Mu-type opioid receptor Ki = 0.22 nM 9.66 Displacement of [3H]-DAMGO from mu-type opioid receptor in guinea pig brain memb... 30924650
Mu-type opioid receptor EC50 = 1.6 nM 8.8 Agonist activity at rat MOR expressed in rat C6 cells assessed as stimulation of... 23419026
Mu-type opioid receptor EC50 = 1.6 nM 8.8 Agonist activity at rat mu-opioid receptor expressed in C6 cell membrane assesse... 26524472
Delta-type opioid receptor Ki = 9.4 nM 8.03 Displacement of [3H]diprenorphine from rat DOR expressed in rat C6 cells after 1... 23419026
Delta-type opioid receptor Ki = 9.4 nM 8.03 Displacement of [3H]diprenorphine from rat delta-opioid receptor expressed in C6... 26524472
Unchecked Ki = 9.4 nM 8.03 Displacement of [3H]-DPDPE from delta-opioid receptor in guinea pig brain membra... 30924650
Kappa-type opioid receptor Ki = 68.0 nM 7.17 Displacement of [3H]diprenorphine from human KOR expressed in CHO cells after 1 ... 23419026
Kappa-type opioid receptor Ki = 68.0 nM 7.17 Displacement of [3H]diprenorphine from human kappa-opioid receptor expressed in ... 26524472
Kappa-type opioid receptor Ki = 68.0 nM 7.17 Displacement of [3H]-U69593 from kappa-type opioid receptor in guinea pig brain ... 30924650
Delta-type opioid receptor EC50 = 110.0 nM 6.96 Agonist activity at rat DOR expressed in rat C6 cells assessed as stimulation of... 23419026
Delta-type opioid receptor EC50 = 110.0 nM 6.96 Agonist activity at rat delta-opioid receptor expressed in C6 cell membrane asse... 26524472
Kappa-type opioid receptor EC50 = 540.0 nM 6.27 Agonist activity at human KOR expressed in CHO cells assessed as stimulation of ... 23419026
Kappa-type opioid receptor EC50 = 540.0 nM 6.27 Agonist activity at human kappa-opioid receptor expressed in CHO cell membrane a... 26524472

Literature References

PubMed DOI Target Context # Activities
23419026 10.1021/jm400050y Mus musculus 4
23419026 10.1021/jm400050y Kappa-type opioid receptor 3
23419026 10.1021/jm400050y Delta-type opioid receptor 3
23419026 10.1021/jm400050y Mu-type opioid receptor 3
26524472 10.1021/acs.jmedchem.5b01270 Mu-type opioid receptor 3
26524472 10.1021/acs.jmedchem.5b01270 Delta-type opioid receptor 3
26524472 10.1021/acs.jmedchem.5b01270 Kappa-type opioid receptor 3
27148755 10.1021/acs.jmedchem.6b00308 Mus musculus 2
30924650 10.1021/acs.jmedchem.9b00219 Unchecked 2
30924650 10.1021/acs.jmedchem.9b00219 ADMET 2
26524472 10.1021/acs.jmedchem.5b01270 Unchecked 1
26524472 10.1021/acs.jmedchem.5b01270 Mus musculus 1
30924650 10.1021/acs.jmedchem.9b00219 Mu-type opioid receptor 1
30924650 10.1021/acs.jmedchem.9b00219 Kappa-type opioid receptor 1
30924650 10.1021/acs.jmedchem.9b00219 Opioid receptor (mu and kappa) 1

Data from ChEMBL 36 via Core Engine