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Compound Detail

CHEMBL215421

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COc1cccc(OC)c1OCCNC[C@H]1COc2ccccc2O1.Cl
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL215421
Phase Preclinical
Structure Type MOL
InChI Key KAHMEWANVDFFCQ-UQKRIMTDSA-N
Parent Compound CHEMBL1182155
Active Moiety CHEMBL1182155
10
Targets
23
Activities
2
Assay Types
0
PK Parameters
20
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

Ki 12 meas. best 9.39
Kd 11 meas. best 9.98

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Alpha-1A adrenergic receptor
CHEMBL319
 Kd 9.98 9.735 0.1 4
Alpha-1A adrenergic receptor
CHEMBL229
 Ki 9.39 9.39 0.4 3
Alpha-1D adrenergic receptor
CHEMBL223
 Ki 9.29 9.29 0.5 3
Alpha-1D adrenergic receptor
CHEMBL326
 Kd 9.2 9.2 0.6 2
Alpha-1B adrenergic receptor
CHEMBL315
 Kd 9.17 9.17 0.7 2
Unchecked
CHEMBL612545
 Kd 9.02 9.02 1.0 1
5-hydroxytryptamine receptor 1A
CHEMBL273
 Ki 8.61 8.61 2.5 3
Alpha-1B adrenergic receptor
CHEMBL232
 Ki 8.24 8.24 5.8 3
Adrenergic receptor alpha-2
CHEMBL2093864
 Kd 6.92 6.92 120.2 1
Alpha-2A adrenergic receptor
CHEMBL327
 Kd 6.92 6.92 120.2 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Alpha-1A adrenergic receptor Kd = 0.1047 nM 9.98 Antagonist activity at alpha1A adrenoceptor in Sprague-Dawley rat prostatic vas ... 23124215
Alpha-1A adrenergic receptor Kd = 0.1047 nM 9.98 Activity at adrenergic alpha 1A receptor assessed as antagonism of noradrenaline... 17125266
Alpha-1A adrenergic receptor Kd = 0.3236 nM 9.49 Activity at adrenergic alpha 1A receptor assessed as antagonsim of noradrenaline... 17125266
Alpha-1A adrenergic receptor Kd = 0.3236 nM 9.49 Antagonist activity at alpha1A adrenoceptor in Sprague-Dawley rat prostate asses... 23124215
Alpha-1A adrenergic receptor Ki = 0.4074 nM 9.39 Displacement of [3H]prazosin from cloned human adrenergic alpha 1A receptor expr... 17125266
Alpha-1A adrenergic receptor Ki = 0.4074 nM 9.39 Displacement of [3H]prazosin from human alpha-1A adrenoreceptor expressed in CHO... 23902232
Alpha-1A adrenergic receptor Ki = 0.4074 nM 9.39 Displacement of [3H]prazosin from human cloned alpha1A adrenoceptor expressed in... 23124215
Alpha-1D adrenergic receptor Ki = 0.5129 nM 9.29 Displacement of [3H]prazosin from cloned human adrenergic alpha 1D receptor expr... 17125266
Alpha-1D adrenergic receptor Ki = 0.5129 nM 9.29 Displacement of [3H]prazosin from human cloned alpha1D adrenoceptor expressed in... 23124215
Alpha-1D adrenergic receptor Ki = 0.5129 nM 9.29 Displacement of [3H]prazosin from human alpha-1D adrenoreceptor expressed in CHO... 23902232
Alpha-1D adrenergic receptor Kd = 0.631 nM 9.2 Antagonist activity at alpha1D adrenoceptor in Sprague-Dawley rat thoracic aorta... 23124215
Alpha-1D adrenergic receptor Kd = 0.631 nM 9.2 Activity at adrenergic alpha 1D receptor assessed as antagonism on noradrenaline... 17125266
Alpha-1B adrenergic receptor Kd = 0.6761 nM 9.17 Antagonist activity at alpha1B adrenoceptor in Sprague-Dawley rat spleen assesse... 23124215
Alpha-1B adrenergic receptor Kd = 0.6761 nM 9.17 Activity at adrenergic alpha 1B receptor assessed as antagonsim of phenylephrine... 17125266
Unchecked Kd = 0.955 nM 9.02 Competitive antagonist at alpha-adrenergic receptor in New Zealand rabbit aorta ... 40029
5-hydroxytryptamine receptor 1A Ki = 2.455 nM 8.61 Displacement of [3H]8-OH-DPAT from 5-HT1A receptor in rat hippocampus 17125266
5-hydroxytryptamine receptor 1A Ki = 2.455 nM 8.61 Displacement of [3H]-8-OH-DPAT from 5-HT1A receptor in rat hippocampal membranes... 23124215
5-hydroxytryptamine receptor 1A Ki = 2.455 nM 8.61 Displacement of [3H]-8-OHDPAT from 5-HT1A receptor in rat hippocampal membranes ... 23902232
Alpha-1B adrenergic receptor Ki = 5.754 nM 8.24 Displacement of [3H]prazosin from cloned human adrenergic alpha 1B receptor expr... 17125266
Alpha-1B adrenergic receptor Ki = 5.754 nM 8.24 Displacement of [3H]prazosin from human cloned alpha1B adrenoceptor expressed in... 23124215

Literature References

PubMed DOI Target Context # Activities
23124215 10.1016/j.ejmech.2012.09.049 Alpha-1A adrenergic receptor 4
17125266 10.1021/jm060358r Alpha-1A adrenergic receptor 3
23902232 10.1021/jm400867d Unchecked 3
23124215 10.1016/j.ejmech.2012.09.049 Unchecked 3
17125266 10.1021/jm060358r Alpha-1B adrenergic receptor 2
23124215 10.1016/j.ejmech.2012.09.049 Alpha-1D adrenergic receptor 2
23124215 10.1016/j.ejmech.2012.09.049 Alpha-1B adrenergic receptor 2
17125266 10.1021/jm060358r Cavia porcellus 2
17125266 10.1021/jm060358r Alpha-1D adrenergic receptor 2
17125266 10.1021/jm060358r Alpha adrenergic receptor 1A and 1B 1
17125266 10.1021/jm060358r Alpha adrenergic receptor 1A and 1D 1
17125266 10.1021/jm060358r Alpha-2A adrenergic receptor 1
17125266 10.1021/jm060358r Unchecked 1
17125266 10.1021/jm060358r Adrenergic receptors; alpha-1 A & B 1
17125266 10.1021/jm060358r Alpha adrenergic receptor (1a and 1d) 1
23124215 10.1016/j.ejmech.2012.09.049 5-hydroxytryptamine receptor 1A 1
23124215 10.1016/j.ejmech.2012.09.049 Adrenergic receptor alpha-2 1
17125266 10.1021/jm060358r 5-hydroxytryptamine receptor 1A 1
23902232 10.1021/jm400867d 5-hydroxytryptamine receptor 1A 1
23902232 10.1021/jm400867d Alpha-1D adrenergic receptor 1

Data from ChEMBL 36 via Core Engine