Compound Detail

CHEMBL452861

LEVOPROPRANOLOL

🧪 Phase II

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🧪 Phase II

CC(C)NC[C@H](O)COc1cccc2ccccc12

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL452861
Name	LEVOPROPRANOLOL
Phase	Phase II
Structure Type	MOL
InChI Key	AQHHHDLHHXJYJD-AWEZNQCLSA-N

Known Names

(-)-propranolol Levopropranolol Propanolol

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

259.4

MW (Da)

2.58

ALogP

HBA

HBD

41.5

PSA (Å²)

0.84

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Chirality	Single Enantiomer

Flags

Natural Product

USAN Stem

-olol

Extended Properties

Molecular Formula	C16H21NO2
MW	259.35
Aromatic Rings	2
Heavy Atoms	19
NP-Likeness	-0.47

Activity Summary

Ki 23 meas. best 9.61

IC50 20 meas. best 9.45

EC50 2 meas. best 8.74

Kd 1 meas. best 9.15

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Beta-2 adrenergic receptor CHEMBL210	Ki	9.61	9.44	0.2	2
Beta-2 adrenergic receptor CHEMBL210	IC50	9.45	9.28	0.4	2
Adrenergic receptor beta CHEMBL2095166	Kd	9.15	9.15	0.7	1
Beta-1 adrenergic receptor CHEMBL213	Ki	8.96	8.905	1.1	2
Beta-1 adrenergic receptor CHEMBL213	EC50	8.74	8.74	1.8	1
Beta-1 adrenergic receptor CHEMBL213	IC50	8.72	8.66	1.9	2
5-hydroxytryptamine receptor 1B CHEMBL3459	Ki	7.77	7.535	17.0	2
5-hydroxytryptamine receptor 1A CHEMBL273	Ki	7.26	7.1167	55.0	3
Beta-3 adrenergic receptor CHEMBL246	Ki	6.91	6.91	124.0	1
5-hydroxytryptamine receptor 1A CHEMBL273	IC50	6.91	6.91	124.0	1
Beta-3 adrenergic receptor CHEMBL246	IC50	6.78	6.78	165.0	1
5-hydroxytryptamine receptor 2B CHEMBL1833	Ki	6.58	6.58	262.0	1
Serotonin 1 (5-HT1) receptor CHEMBL2095159	Ki	6.52	6.52	300.0	1
Cytochrome P450 2D26 CHEMBL2483	IC50	6.46	6.46	350.0	1
5-hydroxytryptamine receptor 2B CHEMBL1833	IC50	6.39	6.39	411.0	1
5-hydroxytryptamine receptor 6 CHEMBL3371	Ki	6.33	6.33	463.0	1
5-hydroxytryptamine receptor 2A CHEMBL224	Ki	6.27	6.27	538.0	1
Sodium-dependent serotonin transporter CHEMBL228	Ki	6.18	6.18	659.0	1
5-hydroxytryptamine receptor 2C CHEMBL225	Ki	6.14	5.995	716.0	2
5-hydroxytryptamine receptor 6 CHEMBL3371	IC50	6.0	6.0	998.0	1
Sodium-dependent serotonin transporter CHEMBL228	IC50	5.91	5.91	1241.0	1
5-hydroxytryptamine receptor 2C CHEMBL225	IC50	5.86	5.86	1368.0	1
Cytochrome P450 2D6 CHEMBL289	IC50	5.85	5.85	1400.0	1
5-hydroxytryptamine receptor 2A CHEMBL224	IC50	5.72	5.72	1883.0	1
Sigma non-opioid intracellular receptor 1 CHEMBL287	Ki	5.55	5.55	2801.0	1
Serotonin 2 (5-HT2) receptor CHEMBL2093870	Ki	5.46	5.345	3500.0	2
5-hydroxytryptamine receptor 1B CHEMBL1898	Ki	5.39	5.39	4100.0	1
Hepatic sodium/bile acid cotransporter CHEMBL5287	IC50	5.21	5.21	6100.0	1
Sigma non-opioid intracellular receptor 1 CHEMBL287	IC50	5.18	5.18	6665.0	1
5-hydroxytryptamine receptor 2A CHEMBL322	Ki	5.09	5.09	8100.0	1
Sodium channel alpha subunits; brain (Types I, II, III) CHEMBL2096682	IC50	4.89	4.89	13000.0	1
Nuclear receptor subfamily 2 group E member 1 CHEMBL1961788	EC50	4.14	4.14	72000.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
CL	214.0	mL.min-1.kg-1	Homo sapiens
CL	51.3	uL.min-1.(10^6cells)-1	Homo sapiens
CL	41.4	uL.min-1.(10^6cells)-1	Homo sapiens
CL	12.9	mL.min-1.kg-1	Homo sapiens
Fu	0.14	-	Not specified
Fu	0.915	-	Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Beta-2 adrenergic receptor	Ki	=	0.244	nM	9.61	DRUGMATRIX: Adrenergic beta2 radioligand binding (ligand: [3H] CGP-12177)	-
Beta-2 adrenergic receptor	IC50	=	0.355	nM	9.45	DRUGMATRIX: Adrenergic beta2 radioligand binding (ligand: [3H] CGP-12177)	-
Beta-2 adrenergic receptor	Ki	=	0.54	nM	9.27	Displacement of [3H]CGP12177 from human recombinant beta2 adrenergic receptor ex...	23403082
Adrenergic receptor beta	Kd	=	0.7	nM	9.15	Binding affinity against Beta adrenergic receptor in C6-2B astrocytoma cells, us...	6120233
Beta-2 adrenergic receptor	IC50	=	0.78	nM	9.11	Displacement of [3H]CGP12177 from human recombinant beta2 adrenergic receptor ex...	23403082
Beta-1 adrenergic receptor	Ki	=	1.102	nM	8.96	DRUGMATRIX: Adrenergic beta1 radioligand binding (ligand: [125I] Cyanopindolol)	-
Beta-1 adrenergic receptor	Ki	=	1.4	nM	8.85	Displacement of [125I]Cynopindolol from human recombinant beta1 adrenergic recep...	23403082
Beta-1 adrenergic receptor	EC50	=	1.8	nM	8.74	Displacement of [125I]cyanopindolol from human recombinant adrenergic beta-1 rec...	16562853
Beta-1 adrenergic receptor	IC50	=	1.908	nM	8.72	DRUGMATRIX: Adrenergic beta1 radioligand binding (ligand: [125I] Cyanopindolol)	-
Beta-1 adrenergic receptor	IC50	=	2.5	nM	8.6	Displacement of [125I]Cynopindolol from human recombinant beta1 adrenergic recep...	23403082
5-hydroxytryptamine receptor 1B	Ki	=	17.0	nM	7.77	Inhibitory activity against 5-hydroxytryptamine 1B receptor of rat striatal memb...	2539480
5-hydroxytryptamine receptor 1B	Ki	=	50.0	nM	7.3	Binding affinity (Ki) to rat cortical membranes at 5-HT1B binding site by using ...	3543362
5-hydroxytryptamine receptor 1A	Ki	=	55.0	nM	7.26	Inhibitory activity against 5-hydroxytryptamine 1A receptor of rat hippocampal t...	2539480
5-hydroxytryptamine receptor 1A	Ki	=	71.0	nM	7.15	DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT1A radioligand binding (ligand: ...	-
5-hydroxytryptamine receptor 1A	Ki	=	115.0	nM	6.94	Evaluated for the binding affinity to hippocampus striatal membranes at 5-hydrox...	3543362
Beta-3 adrenergic receptor	Ki	=	124.0	nM	6.91	DRUGMATRIX: Adrenergic beta3 radioligand binding (ligand: [125I] Cyanopindolol)	-
5-hydroxytryptamine receptor 1A	IC50	=	124.0	nM	6.91	DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT1A radioligand binding (ligand: ...	-
Beta-3 adrenergic receptor	IC50	=	165.0	nM	6.78	DRUGMATRIX: Adrenergic beta3 radioligand binding (ligand: [125I] Cyanopindolol)	-
5-hydroxytryptamine receptor 2B	Ki	=	262.0	nM	6.58	DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2B radioligand binding (ligand: ...	-
Serotonin 1 (5-HT1) receptor	Ki	=	300.0	nM	6.52	Evaluated for binding affinity towards rat cortical membranes at 5-hydroxytrypta...	3543362

Literature References

PubMed	DOI	Target Context	# Activities
23403082	10.1016/j.bmcl.2013.01.025	Beta-1 adrenergic receptor	3
23403082	10.1016/j.bmcl.2013.01.025	Beta-2 adrenergic receptor	3
21998403	10.1124/dmd.111.042309	ADMET	3
3543362	10.1021/jm00384a001	Serotonin 2 (5-HT2) receptor	3
34115934	10.1021/acs.jmedchem.1c00733	Nuclear receptor subfamily 2 group E member 1	2
12477351	10.1021/jm020941h	ATP-dependent translocase ABCB1	2
2836587	10.1021/jm00401a004	Beta-2 adrenergic receptor	2
21998403	10.1124/dmd.111.042309	No relevant target	2
2579237	10.1021/jm00381a019	Sodium channel alpha subunits; brain (Types I, II, III)	2
-	10.6019/CHEMBL4651402	SARS-CoV-2	2
-	10.6019/CHEMBL3301361	ADMET	2
6120233	10.1021/jm00142a017	Adrenergic receptor beta	1
12502361	10.1021/jm0209578	Cytochrome P450 2D6	1
12502361	10.1021/jm0209578	Cytochrome P450 2D3	1
12502361	10.1021/jm0209578	Cytochrome P450 2D26	1
12502361	10.1021/jm0209578	Cytochrome P450 2D1	1
3543362	10.1021/jm00384a001	5-hydroxytryptamine receptor 2C	1
3543362	10.1021/jm00384a001	5-hydroxytryptamine receptor 1B	1
3543362	10.1021/jm00384a001	5-hydroxytryptamine receptor 1A	1
2539480	10.1021/jm00124a021	Adrenergic receptor beta	1

Data from ChEMBL 36 via Core Engine