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Compound Detail

CHEMBL13789

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c1ccc(-c2ccccc2OCC2=NCCN2)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL13789
Phase Preclinical
Structure Type MOL
InChI Key BPRZPBVOIULUSI-UHFFFAOYSA-N
8
Targets
14
Activities
3
Assay Types
0
PK Parameters
14
Publications
0
Known Names

Molecular Properties

252.3
MW (Da)
2.73
ALogP
3
HBA
1
HBD
33.6
PSA (Ų)
0.91
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C16H16N2O
MW 252.32
Aromatic Rings 2
Heavy Atoms 19
NP-Likeness -0.37

Activity Summary

IC50 6 meas. best 7.56
Ki 6 meas. best 8.63
EC50 2 meas. best 8.5

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Nischarin
CHEMBL5221
 Ki 8.63 8.63 2.3 1
Alpha-1A adrenergic receptor
CHEMBL229
 EC50 8.5 8.5 3.2 2
Alpha-1A adrenergic receptor
CHEMBL229
 IC50 7.56 7.37 27.5 2
Adrenergic receptor alpha-2
CHEMBL2093864
 Ki 7.1 7.1 79.4 2
Monoamine oxidase
CHEMBL2095205
 Ki 6.52 6.52 302.0 1
Unchecked
CHEMBL612545
 Ki 6.52 6.52 302.0 1
Nischarin
CHEMBL3923
 Ki 6.5 6.5 316.2 1
Alpha-1D adrenergic receptor
CHEMBL223
 IC50 6.49 6.375 323.6 2
Alpha-1B adrenergic receptor
CHEMBL232
 IC50 6.13 5.875 741.3 2

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Nischarin Ki = 2.344 nM 8.63 Binding affinity to I1 imidazoline binding site in Rattus norvegicus (rat) PC12 ... -
Alpha-1A adrenergic receptor EC50 = 3.162 nM 8.5 Activation of recombinant human adrenergic,alpha-1A receptor expressed in rat-1 ... 11814822
Alpha-1A adrenergic receptor EC50 = 3.162 nM 8.5 Activation of human alpha-1A adrenergic receptor expressed in rat-1 fibroblasts 12419381
Alpha-1A adrenergic receptor IC50 = 27.54 nM 7.56 Binding affinity of compound towards Alpha-1A adrenergic receptor using membrane... 11814822
Alpha-1A adrenergic receptor IC50 = 66.07 nM 7.18 In vitro binding affinity against cloned human alpha-1A-adrenoceptor receptors e... 12419381
Adrenergic receptor alpha-2 Ki = 79.43 nM 7.1 Displacement of [3H]clonidine from Alpha-2 adrenergic receptor of rat cortex mem... 11754577
Adrenergic receptor alpha-2 Ki = 79.43 nM 7.1 Displacement of [3H]clonidine from rat alpha2-adrenoreceptor by liquid scintilla... 26390077
Monoamine oxidase Ki = 302.0 nM 6.52 Displacement of [3H]idazoxan from imidazoline receptor I-2 binding sites in rabb... 11754577
Unchecked Ki = 302.0 nM 6.52 Binding affinity to I2 imidazoline binding site (unknown origin) -
Nischarin Ki = 316.23 nM 6.5 Binding affinity for imidazoline receptor I-2 in rabbit kidney homogenate (relat... 10737743
Alpha-1D adrenergic receptor IC50 = 323.59 nM 6.49 Binding affinity of compound towards human Alpha-1D adrenergic receptor expresse... 11814822
Alpha-1D adrenergic receptor IC50 = 549.54 nM 6.26 In vitro binding affinity against cloned human alpha-1D-adrenoceptor receptors e... 12419381
Alpha-1B adrenergic receptor IC50 = 741.31 nM 6.13 Binding affinity of compound towards human Alpha-1B adrenergic receptor expresse... 11814822
Alpha-1B adrenergic receptor IC50 = 2398.83 nM 5.62 In vitro binding affinity against cloned human alpha-1B-adrenoceptor receptors e... 12419381

Literature References

PubMed DOI Target Context # Activities
11814822 10.1016/s0960-894x(01)00764-8 Alpha-1A adrenergic receptor 3
11814822 10.1016/s0960-894x(01)00764-8 Alpha-1B adrenergic receptor 3
11814822 10.1016/s0960-894x(01)00764-8 Alpha-1D adrenergic receptor 3
12419381 10.1016/s0960-894x(02)00753-9 Alpha-1A adrenergic receptor 3
11754577 10.1021/jm0110082 Adrenergic receptor alpha-2 3
12419381 10.1016/s0960-894x(02)00753-9 Alpha-1B adrenergic receptor 2
12419381 10.1016/s0960-894x(02)00753-9 Alpha-1D adrenergic receptor 2
10737743 10.1021/jm991124t Nischarin 1
11754577 10.1021/jm0110082 Monoamine oxidase 1
11754577 10.1021/jm0110082 Adrenergic receptor alpha-1 1
11754577 10.1021/jm0110082 Unchecked 1
- 10.1007/s00044-004-0023-9 Unchecked 1
- 10.1007/s00044-004-0023-9 Nischarin 1
26390077 10.1021/acs.jmedchem.5b00982 Adrenergic receptor alpha-2 1

Data from ChEMBL 36 via Core Engine