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Compound Detail

CHEMBL404505

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c1ccc2oc(C3=NCCN3)cc2c1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL404505
Phase Preclinical
Structure Type MOL
InChI Key YTJOHEUHUVBKSB-UHFFFAOYSA-N
11
Targets
32
Activities
4
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

186.2
MW (Da)
1.78
ALogP
3
HBA
1
HBD
37.5
PSA (Ų)
0.74
QED
0
Ro5 Violations
1
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C11H10N2O
MW 186.21
Aromatic Rings 2
Heavy Atoms 14
NP-Likeness -0.17

Activity Summary

Ki 27 meas. best 9.89
IC50 3 meas. best 5.19
EC50 1 meas. best 4.42
Kd 1 meas. best 8.05

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Unchecked
CHEMBL612545
 Ki 9.89 8.27 0.1 10
Nischarin
CHEMBL3923
 Ki 8.8 7.98 1.6 2
Amine oxidase [flavin-containing] B
CHEMBL2039
 Kd 8.05 8.05 9.0 1
Alpha-2A adrenergic receptor
CHEMBL1867
 Ki 6.64 5.605 229.1 2
Adrenergic receptor alpha-2
CHEMBL2093864
 Ki 5.72 5.48 1900.0 4
Amine oxidase [flavin-containing] B
CHEMBL2993
 Ki 5.44 5.44 3630.0 1
Nischarin
CHEMBL3923
 IC50 5.19 5.19 6400.0 1
Amine oxidase [flavin-containing] B
CHEMBL2039
 Ki 5.08 4.9133 8300.0 3
Amine oxidase [flavin-containing] B
CHEMBL2993
 IC50 5.04 5.04 9100.0 1
Amine oxidase [flavin-containing] A
CHEMBL1951
 Ki 4.77 4.77 17000.0 1
Amine oxidase [flavin-containing] A
CHEMBL3358
 Ki 4.6 4.6 24940.0 1
Adrenergic receptor alpha-2
CHEMBL2095158
 Ki 4.58 4.58 26302.7 1
Alpha-2C adrenergic receptor
CHEMBL1916
 Ki 4.57 4.57 26915.3 1
Alpha-2B adrenergic receptor
CHEMBL1942
 Ki 4.57 4.57 26915.3 1
Unchecked
CHEMBL612545
 EC50 4.42 4.42 37700.0 1
Amine oxidase [flavin-containing] A
CHEMBL3358
 IC50 4.19 4.19 65000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Unchecked Ki = 0.13 nM 9.89 Displacement of [3H]2-BFI from I2IR in human brain frontal cortex assessed as bi... 32150414
Unchecked Ki = 0.1349 nM 9.87 Displacement of [3H]2-BFI from I2IR in human brain frontal cortex assessed as bi... 32150414
Unchecked Ki = 0.8318 nM 9.08 Displacement of [3H]2-BFI from imidazoline I2 receptor high affinity site in pos... 34118720
Unchecked Ki = 1.288 nM 8.89 Binding affinity to I2 imidazoline binding site in rat brain membrane 24900763
Nischarin Ki = 1.585 nM 8.8 Binding affinity for imidazoline receptor I-2 in rabbit kidney homogenate (relat... 10737743
Unchecked Ki = 1.7 nM 8.77 Inhibition of 1 nM [3H]2-BFI binding to rat whole brain membrane imidazoline rec... 10741563
Unchecked Ki = 3.4 nM 8.47 Displacement of [3H]2BFI from I2 imidazoline binding site in rat brain membrane 20801048
Unchecked Ki = 4.898 nM 8.31 Displacement of [3H]2-BFI from imidazoline I2 receptor in post-mortem human brai... 34118720
Amine oxidase [flavin-containing] B Kd = 9.0 nM 8.05 Inhibition of tranylcypromine binding to human MAOB by fluorescence assay 30455149
Unchecked Ki = 11.48 nM 7.94 Displacement of [3H]2-BFI from I2IR in human brain frontal cortex assessed as bi... 32150414
Nischarin Ki = 70.0 nM 7.16 Binding affinity for rat imidazoline receptor I-1 from crude P2 membranes 14698196
Unchecked Ki = 70.79 nM 7.15 Displacement of [3H]2-BFI from imidazoline I2 receptor low affinity site in post... 34118720
Alpha-2A adrenergic receptor Ki = 229.09 nM 6.64 Displacement of [3H]RX821002 from alpha2-AR in human brain frontal cortex incuba... 32150414
Adrenergic receptor alpha-2 Ki = 1900.0 nM 5.72 Inhibition of 1 nM [3H]RX-821002 binding to rat whole brain membrane Alpha-2 adr... 10741563
Amine oxidase [flavin-containing] B Ki = 3630.0 nM 5.44 Binding affinity to MAOB imidazoline binding site in rat brain mitochondrial hom... 19064321
Adrenergic receptor alpha-2 Ki = 4000.0 nM 5.4 Displacement of [3H]RX-821002 from alpha-2 adrenergic receptor 15013010
Adrenergic receptor alpha-2 Ki = 4000.0 nM 5.4 Binding affinity for rat alpha-2 adrenergic receptor from crude P2 membranes 14698196
Adrenergic receptor alpha-2 Ki = 3980.0 nM 5.4 Displacement of [3H]RX821002 from alpha2 adrenergic receptor in rat brain membra... 20801048
Nischarin IC50 = 6400.0 nM 5.19 Inhibition of 3 nM [3H]clonidine binding to rat kidney membrane imidazoline rece... 10741563
Amine oxidase [flavin-containing] B Ki = 8300.0 nM 5.08 Competitive inhibition of recombinant human MAO-B using farnesylamine as substra... 29339253

Literature References

PubMed DOI Target Context # Activities
34118720 10.1016/j.ejmech.2021.113540 Unchecked 6
32150414 10.1021/acs.jmedchem.9b02080 Unchecked 5
20801048 10.1016/j.bmc.2010.08.005 Unchecked 4
19064321 10.1016/j.bmcl.2008.03.001 Amine oxidase [flavin-containing] B 3
19064321 10.1016/j.bmcl.2008.03.001 Amine oxidase [flavin-containing] A 2
30455149 10.1016/j.bmcl.2018.11.018 Amine oxidase [flavin-containing] B 2
24900763 10.1021/ml400232p Mus musculus 2
10741563 10.1016/s0960-894x(00)00062-7 Unchecked 1
34118720 10.1016/j.ejmech.2021.113540 Z-138 1
10741563 10.1016/s0960-894x(00)00062-7 Adrenergic receptor alpha-2 1
10737743 10.1021/jm991124t Nischarin 1
14698196 10.1016/j.bmcl.2003.09.092 Adrenergic receptor alpha-2 1
19064321 10.1016/j.bmcl.2008.03.001 Unchecked 1
14698196 10.1016/j.bmcl.2003.09.092 Nischarin 1
20801048 10.1016/j.bmc.2010.08.005 Adrenergic receptor alpha-2 1
14698196 10.1016/j.bmcl.2003.09.092 Unchecked 1
24900763 10.1021/ml400232p Alpha-2C adrenergic receptor 1
24900763 10.1021/ml400232p Alpha-2B adrenergic receptor 1
12723959 10.1021/jm021050c Unchecked 1
15013010 10.1016/j.bmcl.2003.12.033 Adrenergic receptor alpha-2 1

Data from ChEMBL 36 via Core Engine