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Compound Detail

CHEMBL556001

2- (2,6-DIMETHOXYPHENOXYETHYL)AMINOMETHYL-1,4-BENZODIOXANE HYDROCHLORIDE (WB 4101)
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COc1cccc(OC)c1OCCNCC1COc2ccccc2O1.Cl
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL556001
Name 2- (2,6-DIMETHOXYPHENOXYETHYL)AMINOMETHYL-1,4-BENZODIOXANE HYDROCHLORIDE (WB 4101)
Phase Preclinical
Structure Type MOL
InChI Key KAHMEWANVDFFCQ-UHFFFAOYSA-N
Parent Compound CHEMBL25554
Active Moiety CHEMBL25554
4
Targets
10
Activities
2
Assay Types
0
PK Parameters
15
Publications
0
Known Names

Molecular Properties

345.4
MW (Da)
2.51
ALogP
6
HBA
1
HBD
58.2
PSA (Ų)
0.74
QED
0
Ro5 Violations
8
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C19H24ClNO5
MW 381.86
Aromatic Rings 2
Heavy Atoms 25
NP-Likeness -0.20

Activity Summary

IC50 6 meas. best 5.4
Kd 4 meas. best 8.83

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Adrenergic receptor alpha-1
CHEMBL1907610
 Kd 8.83 8.83 1.5 2
Adrenergic receptor alpha-2
CHEMBL2093864
 Kd 6.29 6.29 512.9 1
Rattus norvegicus
CHEMBL376
 Kd 6.29 6.29 512.9 1
Plasmodium falciparum
CHEMBL364
 IC50 5.4 5.1 3981.1 6

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Adrenergic receptor alpha-1 Kd = 1.479 nM 8.83 Alpha-1 adrenergic receptor antagonist activity against agonist (norepinephrine)... 6150111
Adrenergic receptor alpha-1 Kd = 1.479 nM 8.83 Alpha-1-Adrenoceptor blocking activity as antagonism of (-)-norepinephrine induc... 2863379
Adrenergic receptor alpha-2 Kd = 512.86 nM 6.29 Alpha-2 adrenergic receptor antagonist activity against agonist (clonidine) in i... 6150111
Rattus norvegicus Kd = 512.86 nM 6.29 Alpha-2-adrenoceptor blocking activity was determined by antagonism of clonidine... 2863379
Plasmodium falciparum IC50 = 3981.07 nM 5.4 Antiplasmodial activity against Plasmodium falciparum W2 after 72 hrs by SYBR gr... 19734910
Plasmodium falciparum IC50 = 5011.87 nM 5.3 Antiplasmodial activity against Plasmodium falciparum GB4 after 72 hrs by SYBR g... 19734910
Plasmodium falciparum IC50 = 7943.28 nM 5.1 Antiplasmodial activity against Plasmodium falciparum 7G8 after 72 hrs by SYBR g... 19734910
Plasmodium falciparum IC50 = 7943.28 nM 5.1 Antiplasmodial activity against Plasmodium falciparum Dd2 after 72 hrs by SYBR g... 19734910
Plasmodium falciparum IC50 = 12589.25 nM 4.9 Antiplasmodial activity against Plasmodium falciparum HB3 after 72 hrs by SYBR g... 19734910
Plasmodium falciparum IC50 = 15848.93 nM 4.8 Antiplasmodial activity against Plasmodium falciparum 3D7 after 72 hrs by SYBR g... 19734910

Literature References

PubMed DOI Target Context # Activities
19734910 10.1038/nchembio.215 Plasmodium falciparum 6
38968440 10.1021/acs.jmedchem.4c00626 Alpha-1A adrenergic receptor 3
38968440 10.1021/acs.jmedchem.4c00626 5-hydroxytryptamine receptor 2A 3
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
6150111 10.1021/jm00378a001 Adrenergic receptor alpha-1 1
6150111 10.1021/jm00378a001 Adrenergic receptor alpha-2 1
2863379 10.1021/jm00147a042 Adrenergic receptor alpha-1 1
2863379 10.1021/jm00147a042 Rattus norvegicus 1
2863379 10.1021/jm00147a042 Unchecked 1
17417631 10.1038/nchembio873 Unchecked 1
23571415 10.1124/mol.112.084152 Solute carrier organic anion transporter family member 1B3 1
23571415 10.1124/mol.112.084152 Solute carrier organic anion transporter family member 1B1 1
- 10.21203/rs.3.rs-23951/v1 SARS-CoV-2 1
- 10.6019/CHEMBL4495564 Replicase polyprotein 1ab 1

Data from ChEMBL 36 via Core Engine