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name Structure Reference Source Properties Activities Metabolism

retigabine

AlkaPlorer ID: AK034899

Synonym: None

IUPAC Name: ethyl N-[2-amino-4-[(4-fluorophenyl)methylamino]phenyl]carbamate

Structure

SMILES: CCOC(O)=NC1=CC=C(NCC2=CC=C(F)C=C2)C=C1N

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InChI: InChI=1S/C16H18FN3O2/c1-2-22-16(21)20-15-8-7-13(9-14(15)18)19-10-11-3-5-12(17)6-4-11/h3-9,19H,2,10,18H2,1H3,(H,20,21)

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InChIKey: PCOBBVZJEWWZFR-UHFFFAOYSA-N

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Reference

PubChem CID: 121892

CAS: 150812-12-7

SuperNatural Ⅲ: SN0281727

NPASS: NPC462099

COCONUT: CNP0256828

Source

Species Genus Family Order Class Phylum Kingdom Domain
Cynanchum wilfordii Cynanchum Apocynaceae Gentianales Magnoliopsida Streptophyta Viridiplantae Eukaryota

Properties Information

Molecule Weight: 303.33700000000005

TPSA？: 79.87

MolLogP？: 3.602000000000001

Number of H-Donors: 3

Number of H-Acceptors: 4

RingCount: 2

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Canis lupus familiaris MDCK Ratio 1.13 None 10.1016/j.bmcl.2015.04.074
Homo sapiens CDGSH iron-sulfur domain-containing protein 1 IC50 nan None 10.1016/j.bmcl.2016.09.009
Homo sapiens CDGSH iron-sulfur domain-containing protein 1 Ki nan None 10.1016/j.bmcl.2016.09.009
Homo sapiens Cytochrome P450 Drug metabolism 3.11 % 10.1021/acs.jmedchem.9b00796
Homo sapiens Glutamate [NMDA] receptor Inhibition nan % 10.1021/acs.jmedchem.7b01199
Homo sapiens HEK293 EC50 1300.0 nM 10.1016/j.bmcl.2004.06.035
Homo sapiens Histone deacetylase 6 Inhibition 0.4 % 10.6019/CHEMBL4808148
Homo sapiens Histone deacetylase 6 Inhibition 14.12 % 10.6019/CHEMBL4808148
Homo sapiens KCNQ4/KCNQ5 EC2 nan None 10.1021/acsmedchemlett.9b00097
Homo sapiens Liver microsome CL 8.0 mL.min-1.kg-1 10.1016/j.bmcl.2015.04.074
Homo sapiens UDP-glucuronosyltransferase 1-1 Km 460000.0 nM 10.1016/j.pharmthera.2004.10.013
Homo sapiens UDP-glucuronosyltransferase 1A4 Km 322000.0 nM 10.1016/j.pharmthera.2004.10.013
Homo sapiens UDP-glucuronosyltransferase 1A4 Km 322000.0 nM 10.1021/jm020397c
Homo sapiens UDP-glucuronosyltransferases (UGTs) Drug metabolism 11.41 % 10.1021/acs.jmedchem.9b00796
Homo sapiens Voltage-gated potassium channel KCNQ3/KCNQ5 EC2 0.34 uM 10.1021/acsmedchemlett.9b00097
Homo sapiens Voltage-gated potassium channel, KQT; KCNQ2(Kv7.2)/KCNQ3(Kv7.3) Activity -26.81 mV 10.1021/acs.jmedchem.9b00796
Homo sapiens Voltage-gated potassium channel, KQT; KCNQ2(Kv7.2)/KCNQ3(Kv7.3) Activity 0.027 None 10.1021/acs.jmedchem.2c00911
Homo sapiens Voltage-gated potassium channel, KQT; KCNQ2(Kv7.2)/KCNQ3(Kv7.3) Activity 0.32 uM 10.1016/j.bmcl.2018.09.036
Homo sapiens Voltage-gated potassium channel, KQT; KCNQ2(Kv7.2)/KCNQ3(Kv7.3) Activity nan None 10.1016/j.ejmech.2011.01.010
Homo sapiens Voltage-gated potassium channel, KQT; KCNQ2(Kv7.2)/KCNQ3(Kv7.3) Activity nan None 10.1021/acs.jmedchem.2c00911
Homo sapiens Voltage-gated potassium channel, KQT; KCNQ2(Kv7.2)/KCNQ3(Kv7.3) delta(V1/2) 10.0 mV 10.1021/acs.jmedchem.2c00911
Homo sapiens Voltage-gated potassium channel, KQT; KCNQ2(Kv7.2)/KCNQ3(Kv7.3) EC2 0.33 uM 10.1021/acsmedchemlett.9b00097
Homo sapiens Voltage-gated potassium channel, KQT; KCNQ2(Kv7.2)/KCNQ3(Kv7.3) EC50 430.0 nM 10.1016/j.ejmech.2011.01.010
Homo sapiens Voltage-gated potassium channel, KQT; KCNQ2(Kv7.2)/KCNQ3(Kv7.3) EC50 1720.0 nM 10.1021/acs.jmedchem.9b00796
Homo sapiens Voltage-gated potassium channel, KQT; KCNQ2(Kv7.2)/KCNQ3(Kv7.3) EC50 2500.0 nM 10.1021/acs.jmedchem.2c00911
Homo sapiens Voltage-gated potassium channel, KQT; KCNQ2(Kv7.2)/KCNQ3(Kv7.3) EC50 4380.0 nM 10.1016/j.bmcl.2019.08.007
Homo sapiens Voltage-gated potassium channel, KQT; KCNQ2(Kv7.2)/KCNQ3(Kv7.3) EC50 11200.0 nM 10.1021/acs.jmedchem.2c00911
Homo sapiens Voltage-gated potassium channel, KQT; KCNQ2(Kv7.2)/KCNQ3(Kv7.3) Emax 99.0 % 10.1016/j.bmcl.2019.08.007
Homo sapiens Voltage-gated potassium channel, KQT; KCNQ2(Kv7.2)/KCNQ3(Kv7.3) FC 0.99 None 10.1021/acs.jmedchem.2c00911
Homo sapiens Voltage-gated potassium channel, KQT; KCNQ2(Kv7.2)/KCNQ3(Kv7.3) Inhibition 100.0 % 10.1016/j.ejmech.2022.114413
Homo sapiens Voltage-gated potassium channel subunit Kv7.1 Activity -8.03 mV 10.1021/acs.jmedchem.0c02252
Homo sapiens Voltage-gated potassium channel subunit Kv7.1 Activity 1.01 None 10.1021/acs.jmedchem.0c02252
Homo sapiens Voltage-gated potassium channel subunit Kv7.1 Activity nan None 10.1016/j.ejmech.2011.01.010
Homo sapiens Voltage-gated potassium channel subunit Kv7.1 Activity nan None 10.1021/acs.jmedchem.9b00796
Homo sapiens Voltage-gated potassium channel subunit Kv7.2 Activity -25.37 mV 10.1021/acs.jmedchem.9b00796
Homo sapiens Voltage-gated potassium channel subunit Kv7.2 Activity 40.0 mV 10.1016/j.bmcl.2018.04.040
Homo sapiens Voltage-gated potassium channel subunit Kv7.2 Activity 40.21 % 10.1016/j.bmcl.2018.04.040
Homo sapiens Voltage-gated potassium channel subunit Kv7.2 Activity 40.21 % 10.1016/j.bmcl.2018.05.019
Homo sapiens Voltage-gated potassium channel subunit Kv7.2 Activity nan None 10.1021/acs.jmedchem.9b00796
Homo sapiens Voltage-gated potassium channel subunit Kv7.2 EC50 150.0 nM 10.1021/jm060989l
Homo sapiens Voltage-gated potassium channel subunit Kv7.2 EC50 350.0 nM 10.1016/j.bmcl.2018.04.040
Homo sapiens Voltage-gated potassium channel subunit Kv7.2 EC50 350.0 nM 10.1016/j.bmcl.2018.05.019
Homo sapiens Voltage-gated potassium channel subunit Kv7.2 EC50 930.0 nM 10.1021/acs.jmedchem.9b00796
Homo sapiens Voltage-gated potassium channel subunit Kv7.2 EC50 4210.0 nM 10.1016/j.bmcl.2022.128841
Homo sapiens Voltage-gated potassium channel subunit Kv7.2 Efficacy 210.0 % 10.1016/j.bmcl.2018.04.040
Homo sapiens Voltage-gated potassium channel subunit Kv7.2 Emax 54.4 mV 10.1016/j.bmcl.2022.128841
Homo sapiens Voltage-gated potassium channel subunit Kv7.2 Ratio 2.0 None 10.1021/acs.jmedchem.9b00796
Homo sapiens Voltage-gated potassium channel subunit Kv7.2 Ratio 2.12 None 10.1016/j.bmcl.2018.04.040
Homo sapiens Voltage-gated potassium channel subunit Kv7.2 Ratio 2.12 None 10.1016/j.bmcl.2018.05.019
Homo sapiens Voltage-gated potassium channel subunit Kv7.2 Ratio 6.0 None 10.1021/acs.jmedchem.9b00796
Homo sapiens Voltage-gated potassium channel subunit Kv7.2 V1/2 -34.3 mV 10.1016/j.bmcl.2022.128841
Homo sapiens Voltage-gated potassium channel subunit Kv7.2 V1/2 -24.4 mV 10.1021/acs.jmedchem.9b00796
Homo sapiens Voltage-gated potassium channel subunit Kv7.2 V1/2 40.0 mV 10.1016/j.bmcl.2018.05.019
Homo sapiens Voltage-gated potassium channel subunit Kv7.3 Activity -39.88 mV 10.1021/acs.jmedchem.9b00796
Homo sapiens Voltage-gated potassium channel subunit Kv7.3 EC50 3900.0 nM 10.1021/acs.jmedchem.9b00796
Homo sapiens Voltage-gated potassium channel subunit Kv7.4 Activity -34.09 mV 10.1021/acs.jmedchem.0c02252
Homo sapiens Voltage-gated potassium channel subunit Kv7.4 Activity -15.19 mV 10.1021/acs.jmedchem.9b00796
Homo sapiens Voltage-gated potassium channel subunit Kv7.4 Activity 2.85 None 10.1021/acs.jmedchem.0c02252
Homo sapiens Voltage-gated potassium channel subunit Kv7.4 Activity 20.0 mV 10.1021/acsmedchemlett.8b00315
Homo sapiens Voltage-gated potassium channel subunit Kv7.4 EC2 nan None 10.1021/acsmedchemlett.9b00097
Homo sapiens Voltage-gated potassium channel subunit Kv7.4 EC50 1980.0 nM 10.1021/acs.jmedchem.9b00796
Homo sapiens Voltage-gated potassium channel subunit Kv7.4 EC50 5900.0 nM 10.1021/acsmedchemlett.8b00315
Homo sapiens Voltage-gated potassium channel subunit Kv7.5 Activity -21.95 mV 10.1021/acs.jmedchem.9b00796
Homo sapiens Voltage-gated potassium channel subunit Kv7.5 Activity 0.09 mV 10.1021/acs.jmedchem.0c02252
Homo sapiens Voltage-gated potassium channel subunit Kv7.5 Activity 3.04 None 10.1021/acs.jmedchem.0c02252
Homo sapiens Voltage-gated potassium channel subunit Kv7.5 EC50 800.0 nM 10.1021/acs.jmedchem.9b00796
Homo sapiens Voltage-gated potassium channel subunit Kv7.5 EC50 3450.0 nM 10.1021/acsmedchemlett.8b00315
Mus musculus Brain EC50 2230.0 nM 10.1021/acs.jmedchem.0c02252
Mus musculus Brain EC50 27320.0 nM 10.1021/acs.jmedchem.0c02252
Mus musculus Mus musculus Activity 6.9 None 10.1021/acs.jmedchem.2c00911
Mus musculus Mus musculus Activity 15.0 % 10.1016/j.bmcl.2018.05.019
Mus musculus Mus musculus Activity 50.0 % 10.1021/acs.jmedchem.0c02252
Mus musculus Mus musculus Activity 60.0 % 10.1021/acs.jmedchem.0c02252
Mus musculus Mus musculus Activity 62.5 % 10.1021/acs.jmedchem.0c02252
Mus musculus Mus musculus Activity 87.5 % 10.1021/acs.jmedchem.0c02252
Mus musculus Mus musculus EC50 20040.0 nM 10.1021/acs.jmedchem.0c02252
Mus musculus Mus musculus EC50 141330.0 nM 10.1021/acs.jmedchem.0c02252
Mus musculus Mus musculus ED50 15.0 mg.kg-1 10.1021/acs.jnatprod.5b00766
Mus musculus Mus musculus ED50 38.6 mg.kg-1 10.1021/acs.jmedchem.0c02252
Mus musculus Mus musculus ED50 56.0 mg.kg-1 10.1021/acs.jmedchem.0c02252
Mus musculus Mus musculus ED50 65.9 mg.kg-1 10.1021/acs.jmedchem.0c02252
Mus musculus Mus musculus ED50 102.5 mg.kg-1 10.1021/acs.jmedchem.0c02252
Mus musculus Mus musculus TIME 0.2893 hr 10.1021/acs.jmedchem.2c00911
Mus musculus Voltage-gated potassium channel subunit Kv7.2 EC50 1300.0 nM 10.1016/j.bmcl.2004.01.069
Mus musculus Voltage-gated potassium channel subunit Kv7.2 EC50 1300.0 nM 10.1016/j.bmcl.2004.10.065
Mus musculus Voltage-gated potassium channel subunit Kv7.2 EC50 1300.0 nM 10.1016/j.bmcl.2013.08.092
Mus musculus Voltage-gated potassium channel subunit Kv7.2 E/Eref 1.6 None 10.1016/j.bmcl.2004.01.069
Mus musculus Voltage-gated potassium channel subunit Kv7.2 E/Eref 1.6 None 10.1016/j.bmcl.2004.10.065
Mus musculus Voltage-gated potassium channel subunit Kv7.2 Increase 269.0 % 10.1016/j.bmcl.2004.01.073
Mus musculus Voltage-gated potassium channel subunit Kv7.2 Ratio 1.6 None 10.1016/j.bmcl.2013.08.092
Rattus norvegicus PC-12 Activity 64.0 % 10.1021/acs.jmedchem.7b01199
Rattus norvegicus PC-12 Activity 73.92 % 10.1021/acs.jmedchem.7b01199
Rattus norvegicus PC-12 Activity nan None 10.1021/acs.jmedchem.7b01199
Rattus norvegicus PC-12 FC 2.0 None 10.1021/acs.jmedchem.7b01199
Rattus norvegicus Potassium voltage-gated channel subfamily KQT member 2/member 3 Activity -34.32 mV 10.1021/acs.jmedchem.0c02252
Rattus norvegicus Potassium voltage-gated channel subfamily KQT member 2/member 3 Activity 1.97 None 10.1021/acs.jmedchem.0c02252
Rattus norvegicus Potassium voltage-gated channel subfamily KQT member 2/member 3 EC50 4150.0 nM 10.1021/acs.jmedchem.0c02252
Rattus norvegicus Rattus norvegicus Activity 0.0 % 10.1016/j.bmcl.2018.05.019
Rattus norvegicus Rattus norvegicus Activity 0.0 % 10.1021/jm901497b
Rattus norvegicus Rattus norvegicus Activity 49.0 % 10.1021/jm901497b
Rattus norvegicus Rattus norvegicus Activity nan None 10.1021/jm901497b
Rattus norvegicus Rattus norvegicus ED50 6.6 mg.kg-1 10.1021/jm060989l
Rattus norvegicus Rattus norvegicus ED50 40.0 mg.kg-1 10.1021/jm060989l
Rattus norvegicus Rattus norvegicus ED50 47.6 mg.kg-1 10.1021/jm060989l
Rattus norvegicus Rattus norvegicus MED 10.0 mg kg-1 10.1021/jm060989l
Rattus norvegicus Voltage-gated potassium channel subunit Kv7.2 Activity -33.2 mV 10.1021/acs.jmedchem.0c02252
Rattus norvegicus Voltage-gated potassium channel subunit Kv7.2 Activity 1.79 None 10.1021/acs.jmedchem.0c02252
Rattus norvegicus Voltage-gated potassium channel subunit Kv7.2 Activity 20.0 mV 10.1021/acsmedchemlett.8b00315
Rattus norvegicus Voltage-gated potassium channel subunit Kv7.2 EC50 2040.0 nM 10.1021/acs.jmedchem.0c02252
Rattus norvegicus Voltage-gated potassium channel subunit Kv7.2 EC50 2170.0 nM 10.1021/acsmedchemlett.8b00315
Rattus norvegicus Voltage-gated potassium channel subunit Kv7.2 Ratio 1.6 None 10.1021/acsmedchemlett.8b00315
Severe acute respiratory syndrome coronavirus 2 Replicase polyprotein 1ab Inhibition 7.961 % 10.6019/CHEMBL4495564
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 Hit score 0.1746 None 10.1101/2020.04.21.054387
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 Inhibition -0.12 % 10.6019/CHEMBL4495565
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 Inhibition 1.55 % 10.21203/rs.3.rs-23951/v1
None ADMET Activity 40.0 % 10.1021/acs.jmedchem.2c00911
None ADMET Activity 62.5 % 10.1021/acs.jmedchem.0c02252
None ADMET Activity 100.0 % 10.1021/acs.jmedchem.0c02252
None ADMET Activity nan None 10.1021/acs.jmedchem.0c02252
None ADMET Cp 40.85 uM 10.1021/acs.jmedchem.0c02252
None ADMET Cp 134.89 uM 10.1021/acs.jmedchem.0c02252
None ADMET Cp 202.2 ng/mg 10.1021/acs.jmedchem.2c00911
None ADMET Ct 8.29 uM 10.1021/acs.jmedchem.0c02252
None ADMET Ct 41.62 uM 10.1021/acs.jmedchem.0c02252
None ADMET Ct 469.2 ng/mg 10.1021/acs.jmedchem.2c00911
None ADMET Drug metabolism 4.7 % 10.1021/acs.jmedchem.2c00911
None ADMET Drug metabolism 17.4 % 10.1021/acs.jmedchem.2c00911
None ADMET IC50 213000.0 nM 10.1016/j.bmcl.2015.04.074
None ADMET permeability 34.2 ucm/s 10.1016/j.bmcl.2015.04.074
None ADMET PPB 79.92 % 10.6019/CHEMBL3301361
None ADMET PPB 86.05 % 10.6019/CHEMBL3301361
None ADMET Ratio 0.11 None 10.1021/acs.jmedchem.0c02252
None ADMET Ratio 0.19 None 10.1021/acs.jmedchem.0c02252
None ADMET Ratio 2.3 None 10.1021/acs.jmedchem.2c00911
None ADMET Ratio 12.3 None 10.1021/acs.jmedchem.0c02252
None ADMET Ratio TD50/ED50 4.9 None 10.1021/acs.jmedchem.0c02252
None ADMET T1/2 2.4 hr 10.1021/acs.jmedchem.2c00911
None ADMET T1/2 6.0 hr 10.1021/acs.jmedchem.9b00796
None ADMET T1/2 16.17 hr 10.1021/acsmedchemlett.9b00097
None ADMET TD50 187.7 mg kg-1 10.1021/acs.jmedchem.0c02252
None ADMET TI 1.6 None 10.1021/jm060989l
None ADMET TI 4.0 None 10.1021/jm060989l
None NON-PROTEIN TARGET Potency 5304.5 nM None
None No relevant target Activity nan None 10.1021/acs.jmedchem.9b00796
None No relevant target Drug degradation 5.0 % 10.1021/acs.jmedchem.9b00796
None No relevant target Drug degradation 9.65 % 10.1021/acs.jmedchem.9b00796
None No relevant target Drug degradation 25.16 % 10.1021/acs.jmedchem.9b00796
None No relevant target Drug degradation 43.5 % 10.1021/acs.jmedchem.9b00796
None No relevant target Drug degradation 47.33 % 10.1021/acs.jmedchem.9b00796
None No relevant target Drug metabolism nan None 10.1021/acs.jmedchem.9b00796
None No relevant target LogP 3.08 None 10.1021/acs.jmedchem.2c00911
None No relevant target LogP 3.08 None 10.1021/acs.jmedchem.9b00796
None No relevant target Retention_time 5.98 min 10.1021/acs.jmedchem.9b00796
None No relevant target Retention_time 14.39 min 10.1021/acs.jmedchem.9b00796
None Unchecked Activity -46.83 mV 10.1021/acs.jmedchem.0c02252
None Unchecked Activity 2.46 None 10.1021/acs.jmedchem.0c02252
None Unchecked Activity 30.0 uM 10.1016/j.bmcl.2018.09.036
None Unchecked Activity nan None 10.1021/acs.jmedchem.7b01199
None Unchecked Drug metabolism 3.41 % 10.1021/acs.jmedchem.9b00796
None Unchecked EC50 1000.0 nM 10.1021/jm060989l
None Unchecked Emax 1.11 mV 10.1016/j.bmcl.2022.128841
None Unchecked Selectivity Index nan None 10.1021/acsmedchemlett.9b00097
None Unchecked V1/2 4.2 mV 10.1016/j.bmcl.2022.128841

Metabolism Information

AKRT ID Reaction Reaction Link ID
AKRT009715 CCOC(=O)Nc1ccc(NCc2ccc(F)cc2)cc1N.O=C(O)[C@H]1O[C@H](OP(=O)(O)OP(=O)(O)OC[C@H]2O[C@@H](n3ccc(=O)[nH]c3=O)[C@H](O)[C@@H]2O)[C@H](O)[C@@H](O)[C@@H]1O>>CCOC(=O)Nc1ccc(NCc2ccc(F)cc2)cc1N[C@@H]1O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]1O enzymemap_34929