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Aminopyrine

AlkaPlorer ID: AK083765

Synonym: None

IUPAC Name: 4-(dimethylamino)-1,5-dimethyl-2-phenylpyrazol-3-one

Structure

SMILES: CC1=C(N(C)C)C(=O)N(C2=CC=CC=C2)N1C

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InChI: InChI=1S/C13H17N3O/c1-10-12(14(2)3)13(17)16(15(10)4)11-8-6-5-7-9-11/h5-9H,1-4H3

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InChIKey: RMMXTBMQSGEXHJ-UHFFFAOYSA-N

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Reference

PubChem CID: 6009

CAS: 144574-10-7

SuperNatural Ⅲ: SN0329448

NPASS: NPC20322

COCONUT: CNP0325858

Source

Species Genus Family Order Class Phylum Kingdom Domain

Properties Information

Molecule Weight: 231.29900000000004

TPSA？: 30.17

MolLogP？: 1.55042

Number of H-Donors: 0

Number of H-Acceptors: 4

RingCount: 2

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Equus caballus Ferritin light chain Potency 316.2 nM None
Homo sapiens Acetylcholinesterase 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 Adrenergic receptor beta Activity -11.5 None 10.1016/S0960-894X(97)00046-2
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 Androgen Receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Arachidonate 15-lipoxygenase Potency 15848.9 nM None
Homo sapiens Caco-2 logPapp -4.44 None 10.1016/j.bmc.2009.08.022
Homo sapiens Caco-2 logPapp -4.44 None 10.1016/j.bmc.2011.03.011
Homo sapiens Chromobox protein homolog 1 Potency 79432.8 nM None
Homo sapiens Cyclooxygenase-1 AC50 3000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Cyclooxygenase-1 AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Cytochrome P450 1A2 AC50 10000.0 nM None
Homo sapiens Cytochrome P450 1A2 Inhibition 10.0 % 10.1124/dmd.111.039180
Homo sapiens Cytochrome P450 1A2 Inhibition nan % 10.1021/tx300075j
Homo sapiens Cytochrome P450 2B6 Inhibition 10.0 % 10.1124/dmd.111.039180
Homo sapiens Cytochrome P450 2C19 AC50 nan None None
Homo sapiens Cytochrome P450 2C19 Inhibition 10.0 % 10.1124/dmd.111.039180
Homo sapiens Cytochrome P450 2C19 Inhibition nan % 10.1021/tx300075j
Homo sapiens Cytochrome P450 2C8 Inhibition 10.0 % 10.1124/dmd.111.039180
Homo sapiens Cytochrome P450 2C9 AC50 nan None None
Homo sapiens Cytochrome P450 2C9 Inhibition 10.0 % 10.1124/dmd.111.039180
Homo sapiens Cytochrome P450 2C9 Inhibition nan % 10.1021/tx300075j
Homo sapiens Cytochrome P450 2D6 AC50 nan None None
Homo sapiens Cytochrome P450 2D6 Inhibition 10.0 % 10.1124/dmd.111.039180
Homo sapiens Cytochrome P450 2D6 Inhibition nan % 10.1021/tx300075j
Homo sapiens Cytochrome P450 3A4 AC50 nan None None
Homo sapiens Cytochrome P450 3A4 Inhibition 10.0 % 10.1124/dmd.111.039180
Homo sapiens Cytochrome P450 3A4 Inhibition nan % 10.1021/tx300075j
Homo sapiens Dopamine D1 receptor AC50 30000.0 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 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Estrogen receptor alpha 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 Geminin Potency 326.4 nM None
Homo sapiens Glutaminase kidney isoform, mitochondrial Potency 35481.3 nM None
Homo sapiens HERG AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Histamine H3 receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Histone deacetylase 6 Inhibition -9.4 % 10.6019/CHEMBL4808148
Homo sapiens Histone deacetylase 6 Inhibition 7.12 % 10.6019/CHEMBL4808148
Homo sapiens Homo sapiens F 100.0 % 10.1124/dmd.111.041665
Homo sapiens Interleukin-8 Potency 66824.2 nM None
Homo sapiens Liver microsome CLH nan None 10.1124/dmd.111.039180
Homo sapiens Liver microsome Drug metabolism nan None 10.1124/dmd.111.039180
Homo sapiens Liver microsome PB 30.9 pmol 10.1124/dmd.111.039180
Homo sapiens Liver microsomes Activity 31.0 pmol 10.1021/tx300075j
Homo sapiens Monoamine oxidase A AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Mu opioid receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Muscarinic acetylcholine receptor M1 AC50 30000.0 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 Nicotinate phosphoribosyltransferase Ki 1.0 nM None
Homo sapiens Norepinephrine transporter AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Nuclear factor erythroid 2-related factor 2 Potency 47307.9 nM None
Homo sapiens Phosphodiesterase 3A AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Phosphodiesterase 4A AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Prelamin-A/C Potency 63.1 nM None
Homo sapiens Progesterone receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Serotonin 1a (5-HT1a) receptor AC50 30000.0 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 transporter AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Skin log Kp -6.62 None 10.1016/j.bmc.2007.07.050
Homo sapiens Thrombin AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Thromboxane A2 receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Thyroid hormone receptor beta-1 Potency 63095.7 nM None
Homo sapiens Thyroid stimulating hormone receptor Potency 7943.3 nM None
Homo sapiens Vascular endothelial growth factor receptor 2 AC50 30000.0 nM 10.1038/s41467-023-40064-9
Mus musculus Mus musculus ED40 60.0 mg kg-1 10.1021/jm00191a017
Mus musculus Mus musculus ED50 19.2 mg.kg-1 10.1021/jm00370a020
Mus musculus Mus musculus ED50 40.0 mg.kg-1 10.1021/jm00191a017
Mus musculus Mus musculus ED50 46.0 mg.kg-1 10.1021/jm00187a013
Mus musculus Mus musculus ED50 53.3 mg.kg-1 10.1021/jm00187a014
Mus musculus Mus musculus ED50 233.0 mg.kg-1 10.1021/jm00187a014
Mus musculus Mus musculus ED50 250.0 mg.kg-1 10.1021/jm00191a017
Mus musculus Mus musculus ED50 640.0 mg.kg-1 10.1021/jm00187a014
Mus musculus Mus musculus ED50 nan None 10.1021/jm00187a014
Mus musculus Mus musculus LD50 385.0 mg.kg-1 10.1021/jm00187a014
Mus musculus Mus musculus LD50 420.0 mg.kg-1 10.1021/jm00187a013
Mus musculus Mus musculus LD50 523.0 mg.kg-1 10.1021/jm00187a014
Mus musculus Mus musculus LD50 523.0 mg.kg-1 10.1021/jm00370a020
Mus musculus Mus musculus LD50 800.0 mg.kg-1 10.1021/jm00191a017
Plasmodium falciparum Plasmodium falciparum Potency 3696.4 nM None
Rattus norvegicus Colon log%Abs 1.32 None 10.1021/jm00211a010
Rattus norvegicus Rattus norvegicus ED50 nan None 10.1021/jm00187a014
Rattus norvegicus Rattus norvegicus Inhibition 11.0 % 10.1021/jm00187a013
Rattus norvegicus Rattus norvegicus Inhibition 17.5 % 10.1021/jm00370a020
Rattus norvegicus Rattus norvegicus Inhibition 21.0 % 10.1016/s0960-894x(01)00008-7
Rattus norvegicus Rattus norvegicus Inhibition 25.0 % 10.1021/jm00187a013
Rattus norvegicus Rattus norvegicus Inhibition 48.2 % 10.1021/jm00187a013
Rattus norvegicus Rattus norvegicus Inhibition 66.0 % 10.1021/jm00211a016
Rattus norvegicus Rattus norvegicus LD50 511.0 mg.kg-1 10.1021/jm00187a014
Rattus norvegicus Rattus norvegicus LD50 2000.0 mg.kg-1 10.1021/jm00187a014
Rattus norvegicus Rattus norvegicus LD50 2560.0 mg.kg-1 10.1021/jm00187a014
Rattus norvegicus Small intestine log%Abs 1.52 None 10.1021/jm00211a010
Rattus norvegicus Solute carrier family 22 member 6 Inhibition 23.8 % None
Rattus norvegicus Thioredoxin reductase 1, cytoplasmic Potency 100000.0 nM None
Severe acute respiratory syndrome coronavirus 2 Replicase polyprotein 1ab Inhibition 16.17 % 10.6019/CHEMBL4495564
Severe acute respiratory syndrome coronavirus 2 Replicase polyprotein 1ab Inhibition 27.62 % 10.6019/CHEMBL4495564
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 Hit score 0.1344 None 10.1101/2020.04.21.054387
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 -0.04 % 10.6019/CHEMBL4495565
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 Inhibition -0.03 % 10.6019/CHEMBL4495565
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 Inhibition 23.9 % 10.21203/rs.3.rs-23951/v1
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 Inhibition index 0.1753 None 10.1101/2020.04.03.023846
None ADMET CL 3.47 uL.min-1.(10^6cells)-1 10.6019/CHEMBL3301361
None ADMET CL nan None 10.1124/dmd.111.039180
None ADMET log10(%HIA +10) 2.041 None 10.1016/j.ejmech.2010.11.005
None ADMET logPapp -4.44 None 10.1124/dmd.111.041665
None ADMET LogP app -462.0 None 10.1016/j.bmc.2007.03.040
None ADMET LogP app -4.76 None 10.1016/j.bmc.2007.03.040
None ADMET LogP app -4.41 None 10.1016/j.bmc.2007.03.040
None ADMET LogP app -4.3 None 10.1016/j.bmc.2007.03.040
None ADMET LogP app -4.14 None 10.1016/j.bmc.2007.03.040
None ADMET logPm -4.23 None 10.1016/j.bmc.2007.03.040
None ADMET Papp 72.31 10^-6 cm/s 10.1016/j.bmc.2007.03.040
None Hepatotoxicity Hepatotoxicity nan None 10.1021/tx900326k
None NON-PROTEIN TARGET Activity nan None 10.1016/j.ejmech.2010.01.071
None NON-PROTEIN TARGET Hepatotoxicity (acute) 0.0 % 10.1016/s0399-8320(04)95062-2
None NON-PROTEIN TARGET Hepatotoxicity (animal toxicity known) nan None 10.1016/s0399-8320(04)95062-2
None NON-PROTEIN TARGET Hepatotoxicity (benign tumour) 0.0 None 10.1016/s0399-8320(04)95062-2
None NON-PROTEIN TARGET Hepatotoxicity (granulomatous hepatitis) 0.0 None 10.1016/s0399-8320(04)95062-2
None NON-PROTEIN TARGET Hepatotoxicity (mechanism) nan None 10.1016/s0399-8320(04)95062-2
None NON-PROTEIN TARGET Hepatotoxicity (moderate) 0.0 % 10.1016/s0399-8320(04)95062-2
None NON-PROTEIN TARGET Hepatotoxicity (moderate) 2.0 None 10.1016/s0399-8320(04)95062-2
None NON-PROTEIN TARGET Hepatotoxicity (time to onset) nan None 10.1016/s0399-8320(04)95062-2
None No relevant target LogD 0.58 None 10.1021/jm00211a010
None No relevant target LogD 0.63 None 10.1124/dmd.111.041665
None No relevant target LogD 1.0 None 10.1021/jf102525e
None No relevant target LogD7.4 0.78 None 10.6019/CHEMBL3301361
None No relevant target LogP -1.1 None 10.1021/jm010289a
None No relevant target LogP -0.59 None 10.1021/jm00218a017
None No relevant target LogP -0.2 None 10.1021/jm00218a017
None No relevant target LogP 0.76 None 10.1021/jm00211a010
None No relevant target LogP 0.82 None 10.1021/jm010289a
None No relevant target LogP 1.0 None 10.1016/j.bmc.2007.03.040
None No relevant target LogP 1.0 None 10.1021/jf102525e
None No relevant target LogP 19.0 None 10.1021/jm00379a002
None No relevant target logPapp -4.76 None 10.1021/jf102525e
None No relevant target Log PNalk -0.68 None 10.1021/jm048980b
None No relevant target pKa 0.0 None 10.1021/jf102525e
None No relevant target pKa 0.3 None 10.1021/jm00211a010
None No relevant target pKa 1.8 None 10.1021/jm00211a010
None No relevant target pKa 4.48 None 10.1016/j.bmc.2007.03.040
None Unchecked Ac50 0.631 uM None
None Unchecked AC50 631.0 nM None
None Unchecked Hepatotoxicity (acute) 6.0 None 10.1016/s0399-8320(04)95062-2
None Unchecked Hepatotoxicity (association with vascular disease) 0.0 None 10.1016/s0399-8320(04)95062-2
None Unchecked Hepatotoxicity (choleostasis) 1.0 None 10.1016/s0399-8320(04)95062-2
None Unchecked Hepatotoxicity (chronic liver disease) 0.0 None 10.1016/s0399-8320(04)95062-2
None Unchecked Hepatotoxicity (cirrhosis) 0.0 None 10.1016/s0399-8320(04)95062-2
None Unchecked Hepatotoxicity (comment) nan None 10.1016/s0399-8320(04)95062-2
None Unchecked Hepatotoxicity (cytolytic) 3.0 None 10.1016/s0399-8320(04)95062-2
None Unchecked Hepatotoxicity (malignant tumour) 0.0 None 10.1016/s0399-8320(04)95062-2
None Unchecked Hepatotoxicity (severe hepatitis) 2.0 None 10.1016/s0399-8320(04)95062-2
None Unchecked Hepatotoxicity (steatosis) 1.0 None 10.1016/s0399-8320(04)95062-2
None Unchecked Hepatotoxicity (successful reintroduction) nan None 10.1016/s0399-8320(04)95062-2
None Unchecked Potency 15848.9 nM None

Metabolism Information

AKRT ID Reaction Reaction Link ID
AKRT001954 C=O.CNc1c(C)n(C)n(-c2ccccc2)c1=O>>Cc1c(N(C)C)c(=O)n(-c2ccccc2)n1C MNXR172057