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Compound Detail

CHEMBL275742

DEXPROPRANOLOL
🧪 Phase II
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🧪 Phase II
CC(C)NC[C@@H](O)COc1cccc2ccccc12

Basic Information

ChEMBL ID CHEMBL275742
Name DEXPROPRANOLOL
Phase Phase II
Structure Type MOL
InChI Key AQHHHDLHHXJYJD-CQSZACIVSA-N

Known Names

Dexpropranolol Propranolol, (r)-
16
Targets
29
Activities
3
Assay Types
0
PK Parameters
20
Publications
2
Known Names

Molecular Properties

259.4
MW (Da)
2.58
ALogP
3
HBA
2
HBD
41.5
PSA (Ų)
0.84
QED
0
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Single Enantiomer

Flags

Natural Product
USAN Stem -olol
USAN Year 1969

Extended Properties

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

Activity Summary

IC50 18 meas. best 7.12
Ki 9 meas. best 7.28
EC50 2 meas. best 5.81

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Beta-2 adrenergic receptor
CHEMBL210
Ki 7.28 7.28 52.0 1
Beta-2 adrenergic receptor
CHEMBL210
IC50 7.12 7.12 76.0 1
5-hydroxytryptamine receptor 1A
CHEMBL273
IC50 6.77 6.04 169.8 2
Beta-1 adrenergic receptor
CHEMBL213
Ki 6.67 6.67 214.0 1
5-hydroxytryptamine receptor 2B
CHEMBL1833
Ki 6.55 6.55 279.0 1
Sodium-dependent serotonin transporter
CHEMBL228
Ki 6.49 6.49 325.0 1
Beta-1 adrenergic receptor
CHEMBL213
IC50 6.43 6.43 370.0 1
Cytochrome P450 2D26
CHEMBL2483
IC50 6.38 6.38 420.0 1
5-hydroxytryptamine receptor 2B
CHEMBL1833
IC50 6.36 6.36 438.0 1
5-hydroxytryptamine receptor 1B
CHEMBL3459
IC50 6.31 6.31 489.8 1
Sodium-dependent serotonin transporter
CHEMBL228
IC50 6.21 6.21 612.0 1
NON-PROTEIN TARGET
CHEMBL3879801
EC50 5.81 5.81 1540.0 1
Sigma non-opioid intracellular receptor 1
CHEMBL287
Ki 5.78 5.78 1670.0 1
5-hydroxytryptamine receptor 1A
CHEMBL273
Ki 5.77 5.66 1700.0 2
Cytochrome P450 2D6
CHEMBL289
IC50 5.72 5.72 1900.0 1
Unchecked
CHEMBL612545
Ki 5.67 5.67 2122.0 1
Unchecked
CHEMBL612545
IC50 5.46 5.46 3448.0 1
Sigma non-opioid intracellular receptor 1
CHEMBL287
IC50 5.4 5.4 3974.0 1
Serotonin 2 (5-HT2) receptor
CHEMBL2093870
IC50 5.1 5.1 7943.3 1
Sodium channel alpha subunits; brain (Types I, II, III)
CHEMBL2096682
IC50 5.0 5.0 10000.0 1
Voltage-gated L-type calcium channel
CHEMBL2095177
Ki 4.84 4.84 14500.0 1
Ileum
CHEMBL613680
IC50 4.57 4.57 27100.0 1
Nuclear receptor subfamily 2 group E member 1
CHEMBL1961788
EC50 4.4 4.4 40000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Beta-2 adrenergic receptor Ki = 52.0 nM 7.28 DRUGMATRIX: Adrenergic beta2 radioligand binding (ligand: [3H] CGP-12177) -
Beta-2 adrenergic receptor IC50 = 76.0 nM 7.12 DRUGMATRIX: Adrenergic beta2 radioligand binding (ligand: [3H] CGP-12177) -
5-hydroxytryptamine receptor 1A IC50 = 169.82 nM 6.77 Binding affinity towards 5-hydroxytryptamine 1A receptor in rat frontal cortex u... 3373482
Beta-1 adrenergic receptor Ki = 214.0 nM 6.67 DRUGMATRIX: Adrenergic beta1 radioligand binding (ligand: [125I] Cyanopindolol) -
5-hydroxytryptamine receptor 2B Ki = 279.0 nM 6.55 DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2B radioligand binding (ligand: ... -
Sodium-dependent serotonin transporter Ki = 325.0 nM 6.49 DRUGMATRIX: Transporter, Serotonin (5-Hydroxytryptamine) (SERT) radioligand bind... -
Beta-1 adrenergic receptor IC50 = 370.0 nM 6.43 DRUGMATRIX: Adrenergic beta1 radioligand binding (ligand: [125I] Cyanopindolol) -
Cytochrome P450 2D26 IC50 = 420.0 nM 6.38 Inhibition of MAMC O-dealkylation mediated by rat Cytochrome P450 2D2 expressed ... 12502361
5-hydroxytryptamine receptor 2B IC50 = 438.0 nM 6.36 DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2B radioligand binding (ligand: ... -
5-hydroxytryptamine receptor 1B IC50 = 489.78 nM 6.31 Binding affinity against 5-HT1B receptor in rat frontal cortex using [3H]-5-HT i... 3373482
Sodium-dependent serotonin transporter IC50 = 612.0 nM 6.21 DRUGMATRIX: Transporter, Serotonin (5-Hydroxytryptamine) (SERT) radioligand bind... -
NON-PROTEIN TARGET EC50 = 1540.0 nM 5.81 Negative inotropic activity in guinea pig left atrium assessed as decrease in at... 18754582
Sigma non-opioid intracellular receptor 1 Ki = 1670.0 nM 5.78 DRUGMATRIX: Sigma1 radioligand binding (ligand: [3H] Haloperidol) -
5-hydroxytryptamine receptor 1A Ki = 1700.0 nM 5.77 Inhibitory activity against 5-hydroxytryptamine 1A receptor of rat hippocampal t... 2539480
Cytochrome P450 2D6 IC50 = 1900.0 nM 5.72 Inhibition of MAMC O-dealkylation mediated by human Cytochrome P450 2D6 expresse... 12502361
Unchecked Ki = 2122.0 nM 5.67 DRUGMATRIX: Sigma2 radioligand binding (ligand: [3H] Ifenprodil) -
5-hydroxytryptamine receptor 1A Ki = 2789.0 nM 5.55 DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT1A radioligand binding (ligand: ... -
Unchecked IC50 = 3448.0 nM 5.46 DRUGMATRIX: Sigma2 radioligand binding (ligand: [3H] Ifenprodil) -
Sigma non-opioid intracellular receptor 1 IC50 = 3974.0 nM 5.4 DRUGMATRIX: Sigma1 radioligand binding (ligand: [3H] Haloperidol) -
5-hydroxytryptamine receptor 1A IC50 = 4880.0 nM 5.31 DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT1A radioligand binding (ligand: ... -

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3301361 ADMET 3
18754582 10.1021/jm800151n NON-PROTEIN TARGET 3
- 10.6019/CHEMBL4651402 SARS-CoV-2 2
34115934 10.1021/acs.jmedchem.1c00733 Nuclear receptor subfamily 2 group E member 1 2
2579237 10.1021/jm00381a019 Sodium channel alpha subunits; brain (Types I, II, III) 2
18754582 10.1021/jm800151n Ileum 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
12502361 10.1021/jm0209578 Cytochrome P450 2D3 1
18754582 10.1021/jm800151n Aorta 1
18754582 10.1021/jm800151n Voltage-gated L-type calcium channel 1
2836587 10.1021/jm00401a004 Beta-2 adrenergic receptor 1
12502361 10.1021/jm0209578 Cytochrome P450 2D6 1
12502361 10.1021/jm0209578 Cytochrome P450 2D4 1
3373482 10.1021/jm00401a007 5-hydroxytryptamine receptor 1A 1
12502361 10.1021/jm0209578 Cytochrome P450 2D26 1
12502361 10.1021/jm0209578 Cytochrome P450 2D1 1
2539480 10.1021/jm00124a021 Adrenergic receptor beta 1
2539480 10.1021/jm00124a021 5-hydroxytryptamine receptor 1B 1
2539480 10.1021/jm00124a021 5-hydroxytryptamine receptor 1A 1
3373482 10.1021/jm00401a007 Serotonin 2 (5-HT2) receptor 1

Data from ChEMBL 36 via Core Engine