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name Structure Reference Source Properties Activities Metabolism

4-[(7-chloroquinolin-4-yl)amino]-2-[(diethylamino)methyl]phenol

AlkaPlorer ID: AK007078

Synonym: None

IUPAC Name: 4-[(7-chloroquinolin-4-yl)amino]-2-(diethylaminomethyl)phenol

Structure

SMILES: CCN(CC)CC1=CC(NC2=CC=NC3=CC(Cl)=CC=C23)=CC=C1O

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InChI: InChI=1S/C20H22ClN3O/c1-3-24(4-2)13-14-11-16(6-8-20(14)25)23-18-9-10-22-19-12-15(21)5-7-17(18)19/h5-12,25H,3-4,13H2,1-2H3,(H,22,23)

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InChIKey: OVCDSSHSILBFBN-UHFFFAOYSA-N

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Reference

PubChem CID: 3647519

CAS: 6398-98-7

COCONUT: CNP0349391

Source

Species Genus Family Order Class Phylum Kingdom Domain
Schizanthus tricolor Schizanthus Solanaceae Solanales Magnoliopsida Streptophyta Viridiplantae Eukaryota

Properties Information

Molecule Weight: 355.8690000000001

TPSA？: 48.39

MolLogP？: 5.179200000000004

Number of H-Donors: 2

Number of H-Acceptors: 4

RingCount: 3

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Chikungunya virus Chikungunya virus Activity 19.0 % 10.1016/j.bmc.2023.117239
Chlorocebus sabaeus Vero CC50 50000.0 nM 10.1101/2020.03.20.999730
Chlorocebus sabaeus Vero C1008 CC50 16780.0 nM 10.6019/CHEMBL4495565
Cricetulus griseus CHO IC50 147157.0 nM 10.1016/j.bmc.2015.07.051
dengue virus type 2 dengue virus type 2 EC50 1080.0 nM 10.1021/acs.jmedchem.5b01653
dengue virus type 2 dengue virus type 2 EC50 7410.0 nM 10.1021/acs.jmedchem.5b01653
dengue virus type 2 dengue virus type 2 IC50 1080.0 nM 10.1016/j.ejmech.2019.05.010
dengue virus type 2 dengue virus type 2 IC90 2690.0 nM 10.1016/j.ejmech.2019.05.010
Homo sapiens Adenosine A1 receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Adenosine A2a receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Adenosine A3 receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Aldehyde oxidase Drug metabolism nan None 10.1021/acs.jmedchem.9b01895
Homo sapiens Alpha-1a adrenergic receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Alpha-2a adrenergic receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Alpha-2b adrenergic receptor AC50 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Alpha-2c adrenergic receptor AC50 4800.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Amyloid-beta A4 protein FC 0.4 None 10.1016/j.bmc.2018.03.016
Homo sapiens Amyloid-beta A4 protein FC 0.5 None 10.1016/j.bmc.2018.03.016
Homo sapiens Amyloid-beta A4 protein IC50 4000.0 nM 10.1016/j.bmc.2018.03.016
Homo sapiens Amyloid-beta A4 protein IC50 5400.0 nM 10.1016/j.bmc.2018.03.016
Homo sapiens Beta-1 adrenergic receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Beta-2 adrenergic receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Bile salt export pump IC50 77760.0 nM 10.1124/dmd.112.047068
Homo sapiens Bradykinin B2 receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Cannabinoid CB1 receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Cathepsin B Inhibition nan % 10.1016/j.ejmech.2018.10.061
Homo sapiens Cholecystokinin A receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Cholecystokinin B receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Cyclooxygenase-2 AC50 6599.9 nM 10.1038/s41467-023-40064-9
Homo sapiens Cytochrome P450 1A2 IC50 41000.0 nM 10.1124/dmd.112.048264
Homo sapiens Cytochrome P450 1A2 Inhibition 10.0 % 10.1124/dmd.111.039180
Homo sapiens Cytochrome P450 2B6 Inhibition 10.0 % 10.1124/dmd.111.039180
Homo sapiens Cytochrome P450 2C19 IC50 50000.0 nM 10.1124/dmd.112.048264
Homo sapiens Cytochrome P450 2C19 Inhibition 10.0 % 10.1124/dmd.111.039180
Homo sapiens Cytochrome P450 2C8 CL 0.608 mL.min-1.g-1 10.1124/dmd.112.047373
Homo sapiens Cytochrome P450 2C8 Inhibition 10.0 % 10.1124/dmd.111.039180
Homo sapiens Cytochrome P450 2C8 Km 1900.0 nM 10.1124/dmd.112.047373
Homo sapiens Cytochrome P450 2C8 Vmax 1460.0 pmol/min 10.1124/dmd.112.047373
Homo sapiens Cytochrome P450 2C9 IC50 50000.0 nM 10.1124/dmd.112.048264
Homo sapiens Cytochrome P450 2C9 Inhibition 10.0 % 10.1124/dmd.111.039180
Homo sapiens Cytochrome P450 2D6 IC50 640.0 nM 10.1124/dmd.112.048264
Homo sapiens Cytochrome P450 2D6 Inhibition 10.0 % 10.1124/dmd.111.039180
Homo sapiens Cytochrome P450 2J2 Activity 7.7 % 10.1124/dmd.111.043505
Homo sapiens Cytochrome P450 2J2 Activity 22.5 % 10.1124/dmd.111.043505
Homo sapiens Cytochrome P450 2J2 IC50 990.0 nM 10.1124/dmd.112.048264
Homo sapiens Cytochrome P450 3A4 IC50 50000.0 nM 10.1124/dmd.112.048264
Homo sapiens Cytochrome P450 3A4 Inhibition 10.0 % 10.1124/dmd.111.039180
Homo sapiens Delta opioid receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Dihydroorotate dehydrogenase Activity nan None 10.1016/j.ejmech.2016.09.073
Homo sapiens Dopamine D1 receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Dopamine D2 receptor AC50 8900.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Dopamine D3 receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Dopamine transporter AC50 16000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Endothelin receptor ET-A AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Equilibrative nucleoside transporter 1 AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Gamma-aminobutyric acid receptor subunit alpha-1/alpha-2/beta-2/gamma-2 AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Ghrelin receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Glucocorticoid receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens HeLa Activity nan None 10.1016/j.ejmech.2018.10.061
Homo sapiens HepG2 EC50 nan None 10.1016/j.ejmech.2015.07.047
Homo sapiens HERG AC50 650.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Histamine H1 receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Histamine H2 receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Histamine H3 receptor AC50 9800.1 nM 10.1038/s41467-023-40064-9
Homo sapiens Huh-7 Inhibition -5.0 % 10.1101/2020.04.13.039917
Homo sapiens Huh-7 Inhibition 1.0 % 10.1101/2020.04.13.039917
Homo sapiens Kappa opioid receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Liver microsome CL 2.1e-05 mL.min-1.g-1 10.1124/dmd.111.039180
Homo sapiens Liver microsome CL 0.224 mL.min-1.g-1 10.1124/dmd.112.047373
Homo sapiens Liver microsome CL 0.829 mL.min-1.g-1 10.1124/dmd.112.047373
Homo sapiens Liver microsome Drug metabolism 2.1 pmol/min 10.1124/dmd.111.039180
Homo sapiens Liver microsome Km 3330.0 nM 10.1124/dmd.112.047373
Homo sapiens Liver microsome Km 5170.0 nM 10.1124/dmd.112.047373
Homo sapiens Liver microsome PB 208.1 pmol 10.1124/dmd.111.039180
Homo sapiens Liver microsome Vmax 1180.0 pmol/min 10.1124/dmd.112.047373
Homo sapiens Liver microsome Vmax 2770.0 pmol/min 10.1124/dmd.112.047373
Homo sapiens Melanocortin receptor 3 AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Monoamine oxidase A AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Motilin receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Mu opioid receptor AC50 10999.9 nM 10.1038/s41467-023-40064-9
Homo sapiens Muscarinic acetylcholine receptor M1 AC50 10999.9 nM 10.1038/s41467-023-40064-9
Homo sapiens Muscarinic acetylcholine receptor M2 AC50 25999.8 nM 10.1038/s41467-023-40064-9
Homo sapiens Muscarinic acetylcholine receptor M2 AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Muscarinic acetylcholine receptor M3 AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Neuronal acetylcholine receptor protein alpha-4 subunit AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Neuropeptide Y receptor type 1 AC50 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Norepinephrine transporter AC50 7900.1 nM 10.1038/s41467-023-40064-9
Homo sapiens Nuclear receptor subfamily 4 group A member 1 Activity nan None 10.1021/acs.jmedchem.0c00894
Homo sapiens Nuclear receptor subfamily 4 group A member 2 Activity nan None 10.1021/acs.jmedchem.0c00894
Homo sapiens Nuclear receptor subfamily 4 group A member 2 Activity nan None 10.1021/acs.jmedchem.0c01779
Homo sapiens Nuclear receptor subfamily 4 group A member 2 EC50 20000.0 nM 10.1021/acs.jmedchem.2c00585
Homo sapiens Nuclear receptor subfamily 4 group A member 2 EC50 36000.0 nM 10.1021/acs.jmedchem.0c01779
Homo sapiens Nuclear receptor subfamily 4 group A member 2 EC50 41000.0 nM 10.1021/acs.jmedchem.1c01077
Homo sapiens Nuclear receptor subfamily 4 group A member 2 EC50 82000.0 nM 10.1021/acs.jmedchem.1c01077
Homo sapiens Nuclear receptor subfamily 4 group A member 2 FC 3.6 None 10.1021/acs.jmedchem.0c01779
Homo sapiens Nuclear receptor subfamily 4 group A member 3 Activity nan None 10.1021/acs.jmedchem.0c00894
Homo sapiens Phosphodiesterase 3A AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Phosphodiesterase 4D AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Pregnane X receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Progesterone receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Serotonin 1a (5-HT1a) receptor AC50 12999.9 nM 10.1038/s41467-023-40064-9
Homo sapiens Serotonin 2a (5-HT2a) receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Serotonin 2b (5-HT2b) receptor AC50 1500.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Serotonin 2b (5-HT2b) receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Serotonin 3a (5-HT3a) receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Serotonin transporter AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Serum albumin pKa 0.12 None 10.1021/acs.jmedchem.0c00046
Homo sapiens Serum albumin pKa 0.64 None 10.1021/acs.jmedchem.0c00046
Homo sapiens Serum albumin PPB 78.8 % 10.1021/acs.jmedchem.0c00046
Homo sapiens SH-SY5Y CC50 10000.0 nM 10.1016/j.bmc.2018.03.016
Homo sapiens SK-N-BE(2) Activity nan None 10.1021/acs.jmedchem.0c00894
Homo sapiens Sodium channel protein type V alpha subunit AC50 50000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Thromboxane A2 receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Type-1 angiotensin II receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Vasopressin V1a receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Vasopressin V2 receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Voltage-gated L-type calcium channel alpha-1C subunit AC50 50000.0 nM 10.1038/s41467-023-40064-9
Mesocricetus auratus BHK-21 CC50 52090.0 nM 10.1021/acs.jmedchem.5b01653
Plasmodium berghei Plasmodium berghei Activity 99.0 % 10.1021/acs.jmedchem.0c01104
Plasmodium berghei Plasmodium berghei Activity 99.9 % 10.1016/j.bmc.2015.07.051
Plasmodium berghei Plasmodium berghei Activity 100.0 % 10.1016/j.bmc.2015.07.051
Plasmodium berghei Plasmodium berghei Activity 100.0 % 10.1021/acsmedchemlett.8b00496
Plasmodium berghei Plasmodium berghei Activity 100.0 % 10.1021/jm500942v
Plasmodium berghei Plasmodium berghei Activity nan None 10.1016/j.bmc.2015.07.051
Plasmodium berghei Plasmodium berghei Activity nan None 10.1021/acsmedchemlett.8b00496
Plasmodium berghei Plasmodium berghei ED50 1.187 mg.kg-1 10.1016/j.ejmech.2016.06.033
Plasmodium berghei Plasmodium berghei Inhibition 28.02 % 10.1016/j.ejmech.2016.06.033
Plasmodium berghei Plasmodium berghei Inhibition 48.24 % 10.1016/j.ejmech.2016.06.033
Plasmodium berghei Plasmodium berghei Inhibition 67.14 % 10.1016/j.ejmech.2016.06.033
Plasmodium berghei Plasmodium berghei Inhibition 94.07 % 10.1016/j.ejmech.2016.06.033
Plasmodium berghei Plasmodium berghei Inhibition 95.5 % 10.1021/acs.jmedchem.6b00759
Plasmodium berghei Plasmodium berghei Inhibition 95.5 % 10.1021/acs.jmedchem.7b00738
Plasmodium berghei Plasmodium berghei Inhibition 95.5 % 10.1021/jm500942v
Plasmodium berghei Plasmodium berghei Inhibition 99.0 % 10.1021/acs.jmedchem.6b00752
Plasmodium berghei Plasmodium berghei Inhibition 99.8 % 10.1021/jm500942v
Plasmodium berghei Plasmodium berghei Inhibition 99.9 % 10.1021/acs.jmedchem.6b00759
Plasmodium berghei Plasmodium berghei Inhibition 99.9 % 10.1021/acs.jmedchem.7b00738
Plasmodium berghei Plasmodium berghei Inhibition 99.9 % 10.1021/jm500942v
Plasmodium berghei Plasmodium berghei Inhibition 100.0 % 10.1016/j.ejmech.2016.09.073
Plasmodium berghei Plasmodium berghei MSD 30.0 day 10.1016/j.bmc.2015.07.051
Plasmodium berghei Plasmodium berghei MSD nan None 10.1016/j.bmc.2015.07.051
Plasmodium berghei Plasmodium berghei MST 28.0 day 10.1021/acsmedchemlett.8b00496
Plasmodium berghei Plasmodium berghei Survival 23.0 % 10.1021/jm500942v
Plasmodium falciparum Hemozoin IC50 8600.0 nM 10.1021/acs.jmedchem.0c02022
Plasmodium falciparum Hemozoin IC50 10000.0 nM 10.1021/acs.jmedchem.2c01516
Plasmodium falciparum Hemozoin IC50 13000.0 nM 10.1039/C8MD00608C
Plasmodium falciparum Hemozoin IC50 21000.0 nM 10.1021/acs.jmedchem.6b00719
Plasmodium falciparum Plasmodium falciparum EC50 5.85 nM 10.1016/j.ejmech.2015.07.047
Plasmodium falciparum Plasmodium falciparum EC50 12.3 nM 10.1016/j.ejmech.2015.07.047
Plasmodium falciparum Plasmodium falciparum IC50 4.0 nM 10.1016/j.bmc.2015.07.051
Plasmodium falciparum Plasmodium falciparum IC50 5.0 nM 10.1016/j.bmc.2015.07.051
Plasmodium falciparum Plasmodium falciparum IC50 6.0 nM 10.1016/j.bmc.2019.01.044
Plasmodium falciparum Plasmodium falciparum IC50 6.0 nM 10.1016/j.ejmech.2016.09.073
Plasmodium falciparum Plasmodium falciparum IC50 8.0 nM 10.1016/j.bmc.2015.07.051
Plasmodium falciparum Plasmodium falciparum IC50 17900.0 nM 10.1016/j.ejmech.2019.111983
Plasmodium falciparum Plasmodium falciparum Ratio IC50 1.6 None 10.1016/j.bmc.2015.07.051
Plasmodium falciparum Plasmodium falciparum Ratio IC50 2.5 None 10.1016/j.bmc.2015.07.051
Rattus norvegicus Androgen Receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Rattus norvegicus Cyclooxygenase-1 AC50 30000.0 nM 10.1038/s41467-023-40064-9
Rattus norvegicus GABA receptor alpha-1 subunit AC50 30000.0 nM 10.1038/s41467-023-40064-9
Rattus norvegicus Glutamate (NMDA) receptor subunit zeta 1 AC50 30000.0 nM 10.1038/s41467-023-40064-9
Severe acute respiratory syndrome coronavirus 2 Replicase polyprotein 1ab Inhibition 14.5 % 10.6019/CHEMBL4495564
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 Hit score 0.1195 None 10.1101/2020.04.21.054387
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 IC50 4070.0 nM 10.6019/CHEMBL4495565
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 IC50 5150.0 nM 10.1101/2020.03.20.999730
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 IC50 19952.62 nM 10.6019/CHEMBL4651402
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 IC50 20000.0 nM 10.6019/CHEMBL4651402
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 Inhibition 60.0 % 10.1101/2020.04.13.039917
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 Inhibition 70.0 % 10.1101/2020.04.13.039917
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 Inhibition 74.34 % 10.6019/CHEMBL4495565
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 Inhibition 90.0 % 10.1101/2020.04.13.039917
Zaire ebolavirus Zaire ebolavirus Activity nan None 10.1016/j.ejmech.2018.10.061
Zika virus Zika virus EC50 2800.0 nM 10.1021/acs.jmedchem.9b00775
None ADMET Activity nan None 10.1124/dmd.112.050054
None ADMET CL 0.021 uL/min 10.1124/dmd.111.039180
None ADMET CL 32.36 uL.min-1.(10^6cells)-1 10.6019/CHEMBL3301361
None ADMET CL 150.0 mL.min-1.g-1 10.6019/CHEMBL3301361
None ADMET CL 431.0 mL.min-1.g-1 10.1021/acsmedchemlett.8b00496
None ADMET CL nan None 10.1124/dmd.111.039180
None ADMET IC50 500000.0 nM 10.1124/dmd.112.050054
None ADMET Inhibition 25.0 % 10.1124/dmd.112.050054
None ADMET Ratio CC50/IC50 37.0 None 10.1016/j.ejmech.2021.113220
None ADMET Selectivity index 4.12 None 10.6019/CHEMBL4495565
None ADMET Selectivity index 9.71 None 10.1101/2020.03.20.999730
None ADMET T1/2 0.09 hr 10.1021/acsmedchemlett.8b00496
None No relevant target IC50 43500.0 nM 10.1016/j.bmc.2015.07.051
None No relevant target LogD7.4 2.9 None 10.6019/CHEMBL3301361
None Unchecked Activity 79.0 % 10.1016/j.ejmech.2016.09.073
None Unchecked Activity nan None 10.1021/acs.jmedchem.0c00894
None Unchecked IC50 400000.0 nM 10.1016/j.ejmech.2016.09.073
None Unchecked Ratio EC50 nan None 10.1016/j.ejmech.2015.07.047
None Unchecked Ratio IC50 36789.25 None 10.1016/j.bmc.2015.07.051

Metabolism Information