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Compound Detail

CHEMBL300662

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C[C@H]1CN(CC[C@H](O)C2CCCCC2)CC[C@@]1(C)c1cccc(O)c1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL300662
Phase Preclinical
Structure Type MOL
InChI Key LVVHEFJXPXAUDD-BULFRSBZSA-N
7
Targets
25
Activities
2
Assay Types
9
PK Parameters
20
Publications
0
Known Names

Molecular Properties

345.5
MW (Da)
4.32
ALogP
3
HBA
2
HBD
43.7
PSA (Ų)
0.83
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 C22H35NO2
MW 345.53
Aromatic Rings 1
Heavy Atoms 25
NP-Likeness 0.77

Activity Summary

Ki 24 meas. best 10.68
IC50 1 meas. best 8.68

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Mu-type opioid receptor
CHEMBL4354
 Ki 10.68 10.085 0.0 2
Mu-type opioid receptor
CHEMBL233
 Ki 10.37 10.0025 0.0 4
Delta-type opioid receptor
CHEMBL236
 Ki 9.51 8.3483 0.3 6
Kappa-type opioid receptor
CHEMBL237
 Ki 9.49 8.62 0.3 4
Mu-type opioid receptor
CHEMBL270
 Ki 9.49 9.44 0.3 2
Kappa-type opioid receptor
CHEMBL3952
 Ki 9.48 8.32 0.3 4
Mu-type opioid receptor
CHEMBL233
 IC50 8.68 8.68 2.1 1
Delta-type opioid receptor
CHEMBL269
 Ki 8.28 7.49 5.2 2

Pharmacokinetic Data

Parameter Value Units Species
Ke 0.24 nM Cavia porcellus
Ke 0.31 nM Cavia porcellus
Ke 1.64 nM -
Ke 0.021 nM Cavia porcellus
Ke 0.312 nM Cavia porcellus
Ke 0.33 nM Cavia porcellus
Ke 0.1 nM Homo sapiens
Ke 0.6 nM Homo sapiens
Ke 0.29 nM Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Mu-type opioid receptor Ki = 0.021 nM 10.68 The compound was tested for antagonist activity by selective inhibition of [35S]... 9599247
Mu-type opioid receptor Ki = 0.043 nM 10.37 Antagonist activity at human mu opioid receptor expressed in CHO cells by [35S]G... 17720493
Mu-type opioid receptor Ki = 0.1 nM 10.0 Binding affinity to human mu opioid receptor expressed in CHO cells 25133923
Mu-type opioid receptor Ki = 0.15 nM 9.82 Displacement of [3H]diprenorphine from human mu opioid receptor expressed in CHO... 17720493
Mu-type opioid receptor Ki = 0.15 nM 9.82 Displacement of [3H]diprenorphine from cloned human mu opioid receptor expressed... 17980586
Delta-type opioid receptor Ki = 0.312 nM 9.51 The compound was tested for antagonist activity by selective inhibition of [35S]... 9599247
Mu-type opioid receptor Ki = 0.32 nM 9.49 Inhibition of [3H]DAMGO binding to Opioid receptor mu 1 of rat brain membranes 9599247
Mu-type opioid receptor Ki = 0.32 nM 9.49 Inhibition of binding of [3H]DAMGO to Opioid receptor mu 1 in guinea pig membran... 12723940
Kappa-type opioid receptor Ki = 0.32 nM 9.49 Antagonist activity at human kappa opioid receptor expressed in CHO cells by [35... 17720493
Kappa-type opioid receptor Ki = 0.33 nM 9.48 The compound was tested for antagonist activity by selective inhibition of [35S]... 9599247
Mu-type opioid receptor Ki = 0.41 nM 9.39 Binding affinity towards mu-opioid receptor by the displacement of [3H]Nal in ra... 8410999
Delta-type opioid receptor Ki = 1.19 nM 8.92 Antagonist activity at human delta opioid receptor expressed in CHO cells by [35... 17720493
Kappa-type opioid receptor Ki = 2.0 nM 8.7 Binding affinity towards kappa opioid receptor by displacement of [3H]EKC in gui... 8410999
Mu-type opioid receptor IC50 = 2.09 nM 8.68 Antagonist activity at human MOR expressed in CHO-K1 cells assessed as cAMP leve... 38810170
Kappa-type opioid receptor Ki = 4.68 nM 8.33 Displacement of [3H]diprenorphine from human kappa opioid receptor expressed in ... 17720493
Kappa-type opioid receptor Ki = 4.68 nM 8.33 Displacement of [3H]diprenorphine from cloned human kappa opioid receptor expres... 17980586
Kappa-type opioid receptor Ki = 4.7 nM 8.33 Binding affinity to human kappa opioid receptor expressed in CHO cells 25133923
Delta-type opioid receptor Ki = 4.82 nM 8.32 Displacement of [3H]bremazocine from human delta opioid receptor expressed in CH... 17720493
Delta-type opioid receptor Ki = 4.82 nM 8.32 Displacement of [3H]bremazocine from cloned human delta opioid receptor expresse... 17980586
Delta-type opioid receptor Ki = 4.8 nM 8.32 Binding affinity to human delta opioid receptor expressed in CHO cells 25133923

Literature References

PubMed DOI Target Context # Activities
38810170 10.1021/acs.jmedchem.4c00333 Mu-type opioid receptor 6
8410999 10.1021/jm00072a002 Kappa-type opioid receptor 4
8410999 10.1021/jm00072a002 Mu-type opioid receptor 3
17720493 10.1016/j.bmcl.2007.08.008 Mu-type opioid receptor 2
17980586 10.1016/j.bmcl.2007.10.025 Mu-type opioid receptor 2
12723940 10.1021/jm030092d Kappa-type opioid receptor 2
12723940 10.1021/jm030092d Delta-type opioid receptor 2
12723940 10.1021/jm030092d Mu-type opioid receptor 2
9599247 10.1021/jm980063g Kappa-type opioid receptor 2
9599247 10.1021/jm980063g Delta-type opioid receptor 2
9599247 10.1021/jm980063g Mu-type opioid receptor 2
17720493 10.1016/j.bmcl.2007.08.008 Kappa-type opioid receptor 2
25133923 10.1021/jm5008177 Kappa-type opioid receptor 2
25133923 10.1021/jm5008177 Delta-type opioid receptor 2
17980586 10.1016/j.bmcl.2007.10.025 Kappa-type opioid receptor 2
17980586 10.1016/j.bmcl.2007.10.025 Delta-type opioid receptor 2
25133923 10.1021/jm5008177 Mu-type opioid receptor 2
17720493 10.1016/j.bmcl.2007.08.008 Delta-type opioid receptor 2
8410999 10.1021/jm00072a002 Delta-type opioid receptor 2
8410999 10.1021/jm00072a002 Adrenergic receptor alpha-2 1

Data from ChEMBL 36 via Core Engine