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Compound Detail

CHEMBL2170062

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Cc1cc(OCCN2CCOCC2)nn1-c1ccc2ccccc2c1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL2170062
Phase Preclinical
Structure Type MOL
InChI Key DGPGXHRHNRYVDH-UHFFFAOYSA-N
5
Targets
27
Activities
2
Assay Types
29
PK Parameters
20
Publications
0
Known Names

Molecular Properties

337.4
MW (Da)
3.04
ALogP
5
HBA
0
HBD
39.5
PSA (Ų)
0.72
QED
0
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C20H23N3O2
MW 337.42
Aromatic Rings 3
Heavy Atoms 25
NP-Likeness -1.86

Activity Summary

Ki 26 meas. best 8.52
IC50 1 meas. best 5.33

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Sigma non-opioid intracellular receptor 1
CHEMBL4153
 Ki 8.52 8.055 3.0 6
Sigma non-opioid intracellular receptor 1
CHEMBL287
 Ki 7.77 7.76 17.0 15
5-hydroxytryptamine receptor 2B
CHEMBL1833
 Ki 6.48 6.48 328.0 1
Unchecked
CHEMBL612545
 Ki 6.0 5.515 1000.0 2
5-hydroxytryptamine receptor 2B
CHEMBL1833
 IC50 5.33 5.33 4700.0 1
Sigma intracellular receptor 2
CHEMBL4105864
 Ki 5.03 5.03 9300.0 2

Pharmacokinetic Data

Parameter Value Units Species
AUC 958.0 ng.hr.mL-1 Mus musculus
AUC 241.1 - Chlorocebus sabaeus
AUC 958.0 ng.hr.mL-1 Mus musculus
AUC 428.0 ng.hr.mL-1 Rattus norvegicus
AUC 958.0 ng.hr.mL-1 Mus musculus
AUC 428.0 ng.hr.mL-1 Rattus norvegicus
CL 65.0 % Mus musculus
CL 109.0 % Rattus norvegicus
CL 189.9 mL.min-1.g-1 Rattus norvegicus
CL 10.7 mL.min-1.g-1 Homo sapiens
CL 65.0 % Mus musculus
CL 109.0 % Rattus norvegicus
Cmax 183.75 nM Mus musculus
Cmax 1843.4 nM Mus musculus
Cmax 892.06 nM Rattus norvegicus
Cmax 1843.4 nM Mus musculus
Cmax 892.06 nM Rattus norvegicus
F 34.0 % Mus musculus
F 15.0 % Rattus norvegicus
F 34.0 % Mus musculus
F 15.0 % Rattus norvegicus
T1/2 0.7 hr Mus musculus
T1/2 1.2 hr Rattus norvegicus
T1/2 0.06 hr Rattus norvegicus
T1/2 1.077 hr Homo sapiens
T1/2 0.7 hr Mus musculus
T1/2 1.2 hr Rattus norvegicus
Vd 2.2 L.kg-1 Mus musculus
Vd 2.9 L.kg-1 Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Sigma non-opioid intracellular receptor 1 Ki = 3.0 nM 8.52 Displacement of [3H]-(+)-pentazocine from sigma-1 receptor in guinea pig brain m... 33372782
Sigma non-opioid intracellular receptor 1 Ki = 6.5 nM 8.19 Displacement of [3H](+)-pentazocine from sigma 1 receptor in guinea pig brain me... 35961067
Sigma non-opioid intracellular receptor 1 Ki = 10.5 nM 7.98 Displacement of [3H]-(+)-pentazocine from sigma 1 receptor in Dunkin Hartley gui... 24735647
Sigma non-opioid intracellular receptor 1 Ki = 10.5 nM 7.98 Displacement of [3H]-(+)-pentazocine from Sigma1 receptor in Dunkin Hartley guin... 27003636
Sigma non-opioid intracellular receptor 1 Ki = 12.9 nM 7.89 Displacement of [3H]-pentazocine from sigma1 receptor in guinea pig brain membra... 36753922
Sigma non-opioid intracellular receptor 1 Ki = 17.0 nM 7.77 Displacement of 3H](+)-pentazocine from human sigma1 receptor expressed in HEK29... 33064947
Sigma non-opioid intracellular receptor 1 Ki = 17.0 nM 7.77 Displacement of [3H](+)-pentazocine from sigma 1 receptor in guinea pig brain me... 37418295
Sigma non-opioid intracellular receptor 1 Ki = 17.0 nM 7.77 Binding affinity to human sigma 1 receptor 36202063
Sigma non-opioid intracellular receptor 1 Ki = 17.0 nM 7.77 Displacement of [3H]-(+)-pentazocine from human sigma1 receptor transfected in H... 33826322
Sigma non-opioid intracellular receptor 1 Ki = 17.0 nM 7.77 Displacement of [3H]-(+)-pentazocine from human sigma-1 receptor transfected in ... 34236190
Sigma non-opioid intracellular receptor 1 Ki = 17.0 nM 7.77 Binding affinity to human sigma-1 receptor 33372782
Sigma non-opioid intracellular receptor 1 Ki = 17.0 nM 7.77 Displacement of [3H]pentazocine from human sigma 1 receptor expressed in HEK293 ... 34223165
Sigma non-opioid intracellular receptor 1 Ki = 17.0 nM 7.77 Displacement of [3H]-(+)-pentazocine from human sigma1 receptor expressed in HEK... 33237785
Sigma non-opioid intracellular receptor 1 Ki = 17.0 nM 7.77 Displacement of [3H]-(+)-pentazocine from recombinant human sigma1 receptor expr... 30904383
Sigma non-opioid intracellular receptor 1 Ki = 17.0 nM 7.77 Displacement of [3H]-(+)-pentazocine from human sigma-1 receptor expressed in HE... 31743642
Sigma non-opioid intracellular receptor 1 Ki = 17.0 nM 7.77 Displacement of [3H]-(+)-pentazocine from recombinant human sigma1 receptor expr... 30108835
Sigma non-opioid intracellular receptor 1 Ki = 17.0 nM 7.77 Displacement of [3H]-(+)-pentazocine from human sigma 1 receptor transfected in ... 30108834
Sigma non-opioid intracellular receptor 1 Ki = 17.0 nM 7.77 Displacement of [3H](+)-pentazocine from human sigma 1 receptor transfected in H... 25658964
Sigma non-opioid intracellular receptor 1 Ki = 17.0 nM 7.77 Displacement of [3H]-(+)-pentazocine from human sigma1 receptor transfected in H... 23560650
Sigma non-opioid intracellular receptor 1 Ki = 17.0 nM 7.77 Displacement of [3H](+)pentazocine from human sigma 1 receptor transfected in HE... 22784008

Literature References

PubMed DOI Target Context # Activities
33237785 10.1021/acs.jmedchem.0c01575 ADMET 12
30108834 10.1039/C7MD00077D Mus musculus 12
33826322 10.1021/acs.jmedchem.1c00244 ADMET 12
22784008 10.1021/jm3007323 Mus musculus 9
30108835 10.1039/C7MD00078B Mus musculus 6
37418295 10.1021/acs.jmedchem.3c00430 Mus musculus 4
33064947 10.1021/acs.jmedchem.0c01127 Mu-type opioid receptor 4
25658964 10.1021/jm501920g Mus musculus 4
22784008 10.1021/jm3007323 No relevant target 4
31743642 10.1021/acs.jmedchem.9b01256 Mu-type opioid receptor 4
33237785 10.1021/acs.jmedchem.0c01575 No relevant target 4
33372782 10.1021/acs.jmedchem.0c01964 ADMET 4
36753922 10.1016/j.ejmech.2023.115178 Mus musculus 3
25658964 10.1021/jm501920g No relevant target 3
32353859 10.1038/s41586-020-2286-9 SARS-CoV-2 3
33372782 10.1021/acs.jmedchem.0c01964 Sigma non-opioid intracellular receptor 1 3
36946301 10.1021/acs.jmedchem.2c02081 Mus musculus 3
22784008 10.1021/jm3007323 Unchecked 2
22784008 10.1021/jm3007323 Sigma non-opioid intracellular receptor 1 2
22784008 10.1021/jm3007323 Cytochrome P450 2C8 2

Data from ChEMBL 36 via Core Engine