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Oxyphenbutazone

AlkaPlorer ID: AK084024

Synonym: None

IUPAC Name: 4-butyl-1-(4-hydroxyphenyl)-2-phenylpyrazolidine-3,5-dione

Structure

SMILES: CCCCC1C(=O)N(C2=CC=CC=C2)N(C2=CC=C(O)C=C2)C1=O

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InChI: InChI=1S/C19H20N2O3/c1-2-3-9-17-18(23)20(14-7-5-4-6-8-14)21(19(17)24)15-10-12-16(22)13-11-15/h4-8,10-13,17,22H,2-3,9H2,1H3

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InChIKey: HFHZKZSRXITVMK-UHFFFAOYSA-N

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Reference

PubChem CID: 4641

CAS: 129-20-4

NPASS: NPC204156

COCONUT: CNP0338876

Source

Species Genus Family Order Class Phylum Kingdom Domain

Properties Information

Molecule Weight: 324.38000000000005

TPSA？: 60.85

MolLogP？: 3.493400000000002

Number of H-Donors: 1

Number of H-Acceptors: 3

RingCount: 3

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Cryptosporidium parvum Cryptosporidium parvum IC50 nan None 10.1016/j.bmc.2010.01.068
Entamoeba histolytica Entamoeba histolytica IC50 nan None 10.1016/j.bmc.2010.01.068
Escherichia coli K-12 Beta-lactamase AmpC Potency 44668.4 nM None
Homo sapiens 15-hydroxyprostaglandin dehydrogenase [NAD+] Potency 39810.7 nM None
Homo sapiens A-375 AC50 35000.0 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 Aldehyde dehydrogenase 1A1 Potency 39810.7 nM None
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 Ataxin-2 Potency 7943.3 nM None
Homo sapiens ATPase family AAA domain-containing protein 5 Potency 17782.8 nM None
Homo sapiens ATPase family AAA domain-containing protein 5 Potency 18348.9 nM None
Homo sapiens Cellular tumor antigen p53 Potency 31622.8 nM None
Homo sapiens Chromobox protein homolog 1 Potency 39810.7 nM None
Homo sapiens Cyclooxygenase-1 AC50 7796.4 nM 10.1038/s41467-023-40064-9
Homo sapiens Cyclooxygenase-1 AC50 21830.8 nM 10.1038/s41467-023-40064-9
Homo sapiens Cytochrome P450 1A2 Inhibition nan % 10.1021/tx300075j
Homo sapiens Cytochrome P450 2C19 Inhibition nan % 10.1021/tx300075j
Homo sapiens Cytochrome P450 2C9 Inhibition nan % 10.1021/tx300075j
Homo sapiens Cytochrome P450 2D6 Inhibition nan % 10.1021/tx300075j
Homo sapiens Cytochrome P450 3A4 Inhibition nan % 10.1021/tx300075j
Homo sapiens Cytochrome P450 3A4 Potency 31622.8 nM None
Homo sapiens DNA-(apurinic or apyrimidinic site) lyase Potency 125.9 nM None
Homo sapiens DNA dC->dU-editing enzyme APOBEC-3G Potency 3162.3 nM None
Homo sapiens DNA polymerase iota Potency 17782.8 nM None
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 Geminin Potency 3162.3 nM None
Homo sapiens Geminin Potency 8199.5 nM None
Homo sapiens Glucagon-like peptide 1 receptor Potency 12589.3 nM None
Homo sapiens Glucose-6-phosphate 1-dehydrogenase IC50 80000.0 nM None
Homo sapiens Guanine nucleotide-binding protein G(s), subunit alpha Potency 12589.3 nM None
Homo sapiens HepG2 Potency 8912.5 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 -31.78 % 10.6019/CHEMBL4808148
Homo sapiens Histone deacetylase 6 Inhibition -0.01 % 10.6019/CHEMBL4808148
Homo sapiens Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 Potency 3548.1 nM None
Homo sapiens Isocitrate dehydrogenase [NADP] cytoplasmic Potency 2909.3 nM None
Homo sapiens Liver microsomes Activity nan None 10.1021/tx300075j
Homo sapiens Liver microsomes Stability nan % 10.1021/tx300075j
Homo sapiens Lysine-specific demethylase 4A Potency 56234.1 nM None
Homo sapiens Microtubule-associated protein tau Potency 15848.9 nM None
Homo sapiens Monoamine oxidase A AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Mothers against decapentaplegic homolog 3 Potency 5623.4 nM None
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 0.3 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 6309.6 nM None
Homo sapiens Nuclear factor erythroid 2-related factor 2 Potency 10691.0 nM None
Homo sapiens Nuclear factor erythroid 2-related factor 2 Potency 25929.0 nM None
Homo sapiens Parathyroid hormone receptor Potency 17782.8 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 Progesterone receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Ras-related protein Rab-9A Potency 6309.6 nM None
Homo sapiens Serine/threonine-protein kinase PLK1 Potency 23778.1 nM None
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 Serum albumin Log K' 0.02 None 10.1021/jm010960b
Homo sapiens Solute carrier organic anion transporter family member 1B1 Inhibition 42.04 % 10.1124/mol.112.084152
Homo sapiens Solute carrier organic anion transporter family member 1B3 Inhibition 83.15 % 10.1124/mol.112.084152
Homo sapiens TAR DNA-binding protein 43 Potency 1000.0 nM None
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 Tyrosyl-DNA phosphodiesterase 1 Potency 580.5 nM None
Homo sapiens Tyrosyl-DNA phosphodiesterase 1 Potency 1032.3 nM None
Homo sapiens Tyrosyl-DNA phosphodiesterase 1 Potency 4109.5 nM None
Homo sapiens Tyrosyl-DNA phosphodiesterase 1 Potency 5173.5 nM None
Homo sapiens Tyrosyl-DNA phosphodiesterase 1 Potency 7176.7 nM None
Homo sapiens Tyrosyl-DNA phosphodiesterase 1 Potency 10137.4 nM None
Homo sapiens Ubiquitin carboxyl-terminal hydrolase 1 Potency 28183.8 nM None
Homo sapiens Ubiquitin carboxyl-terminal hydrolase 1 Potency 56234.1 nM None
Homo sapiens UDP-glucuronosyltransferase 1-6 Activity 0.0 pm/min/mg 10.1146/annurev.pharmtox.40.1.581
Homo sapiens UDP-glucuronosyltransferase 1-9 Activity 0.0 pm/min/mg 10.1146/annurev.pharmtox.40.1.581
Homo sapiens Vascular endothelial growth factor receptor 2 AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Vitamin D receptor Potency 6513.1 nM None
Homo sapiens Vitamin D receptor Potency 7943.3 nM None
Homo sapiens Vitamin D receptor Potency 11220.2 nM None
Homo sapiens Vitamin D receptor Potency 14125.4 nM None
Homo sapiens Vitamin D receptor Potency 15848.9 nM None
Leishmania amazonensis Leishmania amazonensis IC50 nan None 10.1016/j.bmc.2010.01.068
Leishmania donovani Leishmania donovani IC50 nan None 10.1016/j.bmc.2010.01.068
Leishmania infantum Leishmania infantum IC50 nan None 10.1016/j.bmc.2010.01.068
Leishmania major Leishmania major IC50 nan None 10.1016/j.bmc.2010.01.068
Leishmania mexicana Leishmania mexicana IC50 nan None 10.1016/j.bmc.2010.01.068
Mus musculus Mus musculus Activity nan None 10.1016/j.bmcl.2010.02.093
Mus musculus Mus musculus Inhibition 20.0 % 10.1016/j.bmcl.2010.02.093
Mus musculus Mus musculus Inhibition 29.0 % 10.1016/j.bmcl.2010.02.093
Mus musculus Mus musculus Inhibition 50.0 % 10.1016/j.bmcl.2010.02.093
Mus musculus Nuclear receptor ROR-gamma Potency 4466.8 nM None
Mus musculus Nuclear receptor ROR-gamma Potency 5623.4 nM None
Photinus pyralis Luciferin 4-monooxygenase Potency 37933.0 nM None
Plasmodium berghei Glucose-6-phosphate dehydrogenase-6-phosphogluconolactonase IC50 12500.0 nM None
Plasmodium berghei Glucose-6-phosphate dehydrogenase-6-phosphogluconolactonase IC50 80000.0 nM None
Plasmodium falciparum Plasmodium falciparum IC50 15000.0 nM 10.1016/j.bmc.2010.01.068
Plasmodium falciparum Plasmodium falciparum Potency 5221.3 nM None
Pneumocystis carinii Pneumocystis carinii IC50 nan None 10.1016/j.bmc.2010.01.068
Pseudomonas aeruginosa Beta Lactamase IC50 43545.0 nM None
Rattus norvegicus GABA receptor alpha-1 subunit AC50 30000.0 nM 10.1038/s41467-023-40064-9
Rattus norvegicus Rattus norvegicus ID30 0.2 ug 10.1016/j.bmc.2020.115971
Rattus norvegicus Rattus norvegicus ID30 0.3 ug 10.1016/j.bmc.2020.115971
Rattus norvegicus Rattus norvegicus ID50 12.0 ug 10.1016/j.bmc.2020.115971
Rattus norvegicus Rattus norvegicus ID50 46.0 ug 10.1016/j.bmc.2020.115971
Rattus norvegicus Solute carrier family 22 member 6 Ki 32000.0 nM None
Rattus norvegicus Thioredoxin reductase 1, cytoplasmic Potency 7943.3 nM None
Schistosoma mansoni Thioredoxin glutathione reductase Potency 10000.0 nM None
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 index 0.1208 None 10.1101/2020.04.03.023846
Toxoplasma gondii Toxoplasma gondii IC50 nan None 10.1016/j.bmc.2010.01.068
Trichomonas vaginalis Trichomonas vaginalis IC50 nan None 10.1016/j.bmc.2010.01.068
Trypanosoma brucei Trypanosoma brucei IC50 nan None 10.1016/j.bmc.2010.01.068
Trypanosoma brucei brucei Trypanosoma brucei brucei IC50 nan None 10.1016/j.bmc.2010.01.068
Trypanosoma brucei brucei (strain 927/4 GUTat10.1) Putative uncharacterized protein Potency 14125.4 nM None
Trypanosoma brucei rhodesiense Trypanosoma brucei rhodesiense IC50 nan None 10.1016/j.bmc.2010.01.068
Trypanosoma cruzi Trypanosoma cruzi IC50 nan None 10.1016/j.bmc.2010.01.068
None Hepatotoxicity Hepatotoxicity nan None 10.1021/tx900326k
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) 5.0 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) 3.0 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 NON-PROTEIN TARGET IC50 nan None 10.1016/j.bmc.2010.01.068
None No relevant target pKa 4.7 None 10.1016/j.ejmech.2012.03.037
None Unchecked Ac50 28.18 uM None
None Unchecked Ac50 39.81 uM None
None Unchecked AC50 9850.0 nM None
None Unchecked AC50 28183.8 nM None
None Unchecked AC50 39810.7 nM None
None Unchecked Hepatotoxicity (acute) 9.0 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) 3.0 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) 1.0 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) 4.0 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) 3.0 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 IC50 1662.8 nM None
None Unchecked IC50 3293.7 nM None
None Unchecked IC50 4918.9 nM None
None Unchecked IC50 6633.0 nM None
None Unchecked IC50 8826.44 nM None
None Unchecked IC50 10000.0 nM None
None Unchecked IC50 20000.0 nM None
None Unchecked IC50 25000.0 nM None
None Unchecked IC50 229300.0 nM 10.1016/j.ejmech.2022.114144
None Unchecked IC50 229300.0 nM 10.1039/d1md00274k
None Unchecked Ki 44500.0 nM 10.1016/j.ejmech.2022.114144
None Unchecked Potency 891.3 nM None
None Unchecked Potency 2818.4 nM None
None Unchecked Potency 3162.3 nM None
None Unchecked Potency 5623.4 nM None
None Unchecked Potency 8912.5 nM None
None Unchecked Potency 10000.0 nM None
None Unchecked Potency 11220.2 nM None
None Unchecked Potency 21192.3 nM None
None Unchecked Potency 25118.9 nM None
None Unchecked Potency 29092.9 nM None
None Unchecked Potency 35481.3 nM None
None Unchecked Potency 39810.7 nM None

Metabolism Information