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Cotinine

AlkaPlorer ID: AK000084

Synonym: None

IUPAC Name: (5S)-1-methyl-5-pyridin-3-ylpyrrolidin-2-one

Structure

SMILES: CN1C(=O)CC[C@H]1C1=CC=CN=C1

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InChI: InChI=1S/C10H12N2O/c1-12-9(4-5-10(12)13)8-3-2-6-11-7-8/h2-3,6-7,9H,4-5H2,1H3/t9-/m0/s1

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InChIKey: UIKROCXWUNQSPJ-VIFPVBQESA-N

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Properties Information

Molecule Weight: 176.21900000000002

TPSA？: 33.2

MolLogP？: 1.3749

Number of H-Donors: 0

Number of H-Acceptors: 2

RingCount: 2

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Acinetobacter baumannii Acinetobacter baumannii Inhibition 6.43 % 10.6019/CHEMBL4513141
Candida albicans Candida albicans Inhibition 4.46 % 10.6019/CHEMBL4513141
Cryptococcus neoformans Cryptococcus neoformans Inhibition -1.87 % 10.6019/CHEMBL4513141
Electrophorus electricus Acetylcholinesterase Inhibition 28.65 % 10.1016/j.bmc.2012.09.040
Equus caballus Cholinesterase Inhibition -0.23 % 10.1016/j.bmc.2012.09.040
Escherichia coli Escherichia coli Inhibition 7.12 % 10.6019/CHEMBL4513141
Homo sapiens Acetylcholinesterase Inhibition 50.0 % 10.1016/j.bmc.2020.115820
Homo sapiens Adenosine A1 receptor Inhibition 50.0 % 10.1016/j.bmc.2020.115820
Homo sapiens Adenosine A2a receptor Inhibition 50.0 % 10.1016/j.bmc.2020.115820
Homo sapiens Alpha-1a adrenergic receptor Inhibition 50.0 % 10.1016/j.bmc.2020.115820
Homo sapiens Alpha-1b adrenergic receptor Inhibition 50.0 % 10.1016/j.bmc.2020.115820
Homo sapiens Alpha-2a adrenergic receptor Inhibition 50.0 % 10.1016/j.bmc.2020.115820
Homo sapiens Alpha-2b adrenergic receptor Inhibition 50.0 % 10.1016/j.bmc.2020.115820
Homo sapiens Alpha-2c adrenergic receptor Inhibition 50.0 % 10.1016/j.bmc.2020.115820
Homo sapiens ATPase family AAA domain-containing protein 5 Potency 6510.4 nM None
Homo sapiens Beta-1 adrenergic receptor Inhibition 50.0 % 10.1016/j.bmc.2020.115820
Homo sapiens Beta-2 adrenergic receptor Inhibition 50.0 % 10.1016/j.bmc.2020.115820
Homo sapiens Bradykinin B2 receptor Inhibition 50.0 % 10.1016/j.bmc.2020.115820
Homo sapiens Cysteinyl leukotriene receptor 1 Inhibition 50.0 % 10.1016/j.bmc.2020.115820
Homo sapiens Cytochrome P450 1A2 IC50 5400000.0 nM 10.1021/jm0489713
Homo sapiens Cytochrome P450 2A6 IC50 400000.0 nM None
Homo sapiens Cytochrome P450 2A6 IC50 35000000.0 nM 10.1021/jm049536b
Homo sapiens Cytochrome P450 3A4 IC50 nan None None
Homo sapiens Dopamine D1 receptor Inhibition 50.0 % 10.1016/j.bmc.2020.115820
Homo sapiens Dopamine D2 receptor Inhibition 50.0 % 10.1016/j.bmc.2020.115820
Homo sapiens Dopamine D3 receptor Inhibition 50.0 % 10.1016/j.bmc.2020.115820
Homo sapiens Dopamine D4 receptor Inhibition 50.0 % 10.1016/j.bmc.2020.115820
Homo sapiens Dopamine transporter Inhibition 50.0 % 10.1016/j.bmc.2020.115820
Homo sapiens Endothelin receptor ET-A Inhibition 50.0 % 10.1016/j.bmc.2020.115820
Homo sapiens Flap endonuclease 1 Potency 6701.6 nM None
Homo sapiens GABA-B receptor 1 Inhibition 50.0 % 10.1016/j.bmc.2020.115820
Homo sapiens GABA receptor alpha-1 subunit Inhibition 50.0 % 10.1016/j.bmc.2020.115820
Homo sapiens Galactocerebrosidase Potency 562.3 nM None
Homo sapiens HERG Inhibition 50.0 % 10.1016/j.bmc.2020.115820
Homo sapiens Histamine H1 receptor Inhibition 50.0 % 10.1016/j.bmc.2020.115820
Homo sapiens Histamine H2 receptor Inhibition 50.0 % 10.1016/j.bmc.2020.115820
Homo sapiens Histamine H3 receptor Inhibition 50.0 % 10.1016/j.bmc.2020.115820
Homo sapiens Histone deacetylase 6 Inhibition -16.76 % 10.6019/CHEMBL4808148
Homo sapiens Histone deacetylase 6 Inhibition -4.66 % 10.6019/CHEMBL4808148
Homo sapiens Homo sapiens CL 0.8 mL.min-1.kg-1 10.1021/jm901371v
Homo sapiens Homo sapiens CL 0.89 mL.min-1.kg-1 10.1021/jm901371v
Homo sapiens Homo sapiens CL_renal 0.1 mL.min-1.kg-1 10.1021/jm901371v
Homo sapiens Homo sapiens Fa 0.9 None 10.1021/jm901371v
Homo sapiens Homo sapiens F_fraction 0.9 None 10.1021/jm901371v
Homo sapiens Homo sapiens Fg 1.04 None 10.1021/jm901371v
Homo sapiens Homo sapiens Fh 0.97 None 10.1021/jm901371v
Homo sapiens Homo sapiens Vdss 1.1 L.kg-1 10.1021/jm901371v
Homo sapiens Leukotriene B4 receptor 1 Inhibition 50.0 % 10.1016/j.bmc.2020.115820
Homo sapiens Mu opioid receptor Inhibition 50.0 % 10.1016/j.bmc.2020.115820
Homo sapiens Muscarinic acetylcholine receptor M1 Inhibition 50.0 % 10.1016/j.bmc.2020.115820
Homo sapiens Muscarinic acetylcholine receptor M2 Inhibition 50.0 % 10.1016/j.bmc.2020.115820
Homo sapiens Muscarinic acetylcholine receptor M3 Inhibition 50.0 % 10.1016/j.bmc.2020.115820
Homo sapiens Muscarinic acetylcholine receptor M4 Inhibition 50.0 % 10.1016/j.bmc.2020.115820
Homo sapiens Muscarinic acetylcholine receptor M5 Inhibition 50.0 % 10.1016/j.bmc.2020.115820
Homo sapiens Neurokinin 1 receptor Inhibition 50.0 % 10.1016/j.bmc.2020.115820
Homo sapiens Neuropeptide Y receptor type 2 Inhibition 50.0 % 10.1016/j.bmc.2020.115820
Homo sapiens Phosphodiesterase 5A Inhibition 50.0 % 10.1016/j.bmc.2020.115820
Homo sapiens Protein kinase C alpha Inhibition 50.0 % 10.1016/j.bmc.2020.115820
Homo sapiens Regulator of G-protein signaling 4 Potency 16833.6 nM None
Homo sapiens Regulator of G-protein signaling 4 Potency 26679.5 nM None
Homo sapiens Serotonin 1a (5-HT1a) receptor Inhibition 50.0 % 10.1016/j.bmc.2020.115820
Homo sapiens Serotonin 1d (5-HT1d) receptor Inhibition 50.0 % 10.1016/j.bmc.2020.115820
Homo sapiens Serotonin 2a (5-HT2a) receptor Inhibition 50.0 % 10.1016/j.bmc.2020.115820
Homo sapiens Serotonin 2c (5-HT2c) receptor Inhibition 50.0 % 10.1016/j.bmc.2020.115820
Homo sapiens Serotonin 3a (5-HT3a) receptor Inhibition 50.0 % 10.1016/j.bmc.2020.115820
Homo sapiens Serotonin 4 (5-HT4) receptor Inhibition 50.0 % 10.1016/j.bmc.2020.115820
Homo sapiens Serotonin 7 (5-HT7) receptor Inhibition 50.0 % 10.1016/j.bmc.2020.115820
Homo sapiens Serotonin transporter Inhibition 50.0 % 10.1016/j.bmc.2020.115820
Homo sapiens Sigma intracellular receptor 2 Inhibition 50.0 % 10.1016/j.bmc.2020.115820
Homo sapiens Sigma opioid receptor Inhibition 50.0 % 10.1016/j.bmc.2020.115820
Homo sapiens Solute carrier organic anion transporter family member 1B1 Inhibition 106.54 % 10.1124/mol.112.084152
Homo sapiens Solute carrier organic anion transporter family member 1B3 Inhibition 103.03 % 10.1124/mol.112.084152
Homo sapiens Thromboxane A2 receptor Inhibition 50.0 % 10.1016/j.bmc.2020.115820
Homo sapiens Type-1 angiotensin II receptor Inhibition 50.0 % 10.1016/j.bmc.2020.115820
Homo sapiens Voltage-gated L-type calcium channel Inhibition 50.0 % 10.1016/j.bmc.2020.115820
Klebsiella pneumoniae Klebsiella pneumoniae Inhibition 5.32 % 10.6019/CHEMBL4513141
Musca domestica Acetylcholinesterase IC50 260000000.0 nM 10.1584/jpestics.17.4_231
Musca domestica Musca domestica FC 0.03 None 10.1584/jpestics.17.4_231
Musca domestica Nicotinic acetylcholine receptor alpha 5 subunit Ki 1000000.0 nM 10.1584/jpestics.17.4_231
Mus musculus Cytochrome P450 2A5 IC50 1500000.0 nM 10.1021/jm049536b
Plasmodium falciparum Plasmodium falciparum IC50 12589.25 nM 10.1038/nchembio.215
Plasmodium falciparum Plasmodium falciparum Potency 1069.1 nM None
Pseudomonas aeruginosa Pseudomonas aeruginosa Inhibition 2.81 % 10.6019/CHEMBL4513141
Rattus norvegicus Neuronal acetylcholine receptor; alpha4/beta2 EC50 21000.0 nM 10.1016/j.bmc.2020.115820
Rattus norvegicus Neuronal acetylcholine receptor; alpha4/beta2 Ki 3000.0 nM 10.1016/j.bmc.2020.115820
Severe acute respiratory syndrome coronavirus 2 Replicase polyprotein 1ab Inhibition 2.176 % 10.6019/CHEMBL4495564
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 -6.19 % 10.21203/rs.3.rs-23951/v1
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 Inhibition -0.09 % 10.6019/CHEMBL4495565
Staphylococcus aureus Staphylococcus aureus Inhibition -20.45 % 10.6019/CHEMBL4513141
None ADMET CL 0.89 mL.min-1.kg-1 10.1124/dmd.108.020479
None ADMET logP(lung) -0.18 None 10.1016/j.ejmech.2007.04.002
None ADMET MRT 21.0 hr 10.1124/dmd.108.020479
None ADMET Ratio 42.8 None 10.1021/jm049536b
None ADMET T1/2 17.0 hr 10.1124/dmd.108.020479
None ADMET T1/2 19.0 hr 10.1016/j.bmc.2020.115820
None ADMET Vdss 1.1 L.kg-1 10.1124/dmd.108.020479
None NON-PROTEIN TARGET Activity 60.5 % 10.1016/j.bmcl.2014.02.008
None NON-PROTEIN TARGET Activity 61.6 % 10.1016/j.bmcl.2014.02.008
None NON-PROTEIN TARGET Activity 61.7 % 10.1016/j.bmcl.2014.02.008
None NON-PROTEIN TARGET Activity 63.8 % 10.1016/j.bmcl.2014.02.008
None NON-PROTEIN TARGET Activity 66.5 % 10.1016/j.bmcl.2014.02.008
None NON-PROTEIN TARGET Activity 72.8 % 10.1016/j.bmcl.2014.02.008
None NON-PROTEIN TARGET Activity 76.3 % 10.1016/j.bmcl.2014.02.008
None NON-PROTEIN TARGET Activity 76.8 % 10.1016/j.bmcl.2014.02.008
None NON-PROTEIN TARGET Activity 78.1 % 10.1016/j.bmcl.2014.02.008
None NON-PROTEIN TARGET Activity 82.3 % 10.1016/j.bmcl.2014.02.008
None NON-PROTEIN TARGET Activity nan None 10.1016/j.bmcl.2014.02.008
None No relevant target pKa 4.5 None 10.1584/jpestics.17.4_231
None Unchecked Activity 20.0 % 10.1016/j.bmc.2020.115820
None Unchecked IC50 33330.0 nM None
None Unchecked Inhibition 50.0 % 10.1016/j.bmc.2020.115820
None Unchecked Inhibition nan % 10.1038/nchembio873
None Unchecked Ki 1000000.0 nM 10.1584/jpestics.17.4_231
None Unchecked Potency 1995.3 nM None
None Unchecked Ratio IC50 nan None None

Metabolism Information

AKRT ID Reaction Reaction Link ID
AKRT010501 CN1C(=O)CC[C@H]1c1cccnc1.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>>CN1C(=O)CC[C@H]1c1ccc[n+]([C@@H]2O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]2O)c1 enzymemap_34857
AKRT010502 CN1C(=O)CC[C@H]1c1cccnc1.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>>CN1C(=O)CC[C@H]1c1ccc[n+]([C@H]2O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]2O)c1 RXN66-168
AKRT010503 CN1C(=O)CC[C@H]1c1cccnc1>>CN1C(=O)CC[C@@]1(O)c1cccnc1 RXN66-163
AKRT010504 CN1C(=O)CC[C@H]1c1cccnc1>>CN1C(=O)CC[C@H]1c1ccc[n+](O)c1 RXN66-166
AKRT010505 CN1C(=O)CC[C@H]1c1cccnc1>>CN1C(=O)[C@H](O)C[C@H]1c1cccnc1 RXN66-161
AKRT010506 CN1C(=O)CC[C@H]1c1cccnc1>>O=C1CC[C@@H](c2cccnc2)N1CO RXN66-169
AKRT014450 C[N+]1=CCC[C@H]1c1cccnc1>>CN1C(=O)CC[C@H]1c1cccnc1 RXN66-62