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toxoflavin

AlkaPlorer ID: AK018802

Synonym: '1-methylreumycin', 'Toxoflavin', 'xanthotricin', '1,6-dimethylpyrimido5,4-e1,2,4triazine-5,7(1H,6H)-dione', 'MLS000087831', 'SMR000024051', 'toxoflavin', '1,6-dimethylpyrimido5,4-e1,2,4triazine-5,7-dione', 'NC72', 'toxoflavine', 'MLSMR', 'PKF118-310', 'NSC67078', '1,6-dimethylpyrimido(5,4-e)-as-triazine-5,7(1H,6H)-dione', 'Xanthothricin', 'xanthothricin'

IUPAC Name: 1,6-dimethylpyrimido[5,4-e][1,2,4]triazine-5,7-dione

Structure

SMILES: CN1N=CN=C2C1=NC(=O)N(C)C2=O

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InChI: InChI=1S/C7H7N5O2/c1-11-6(13)4-5(10-7(11)14)12(2)9-3-8-4/h3H,1-2H3

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InChIKey: SLGRAIAQIAUZAQ-UHFFFAOYSA-N

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Properties Information

Molecule Weight: 193.166

TPSA？: 82.66999999999999

MolLogP？: -1.6262

Number of H-Donors: 0

Number of H-Acceptors: 7

RingCount: 2

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Arabidopsis thaliana 4-diphosphocytidyl-2-C-methyl-D-erythritol kinase, chloroplastic Potency 1187.3 nM None
Bacillus anthracis Anthrax lethal factor Potency 1258.9 nM None
Bacillus subtilis 4'-phosphopantetheinyl transferase ffp Potency 63095.7 nM None
Cricetulus griseus CHO Potency 8912.5 nM None
Escherichia coli K-12 Beta-lactamase AmpC Potency 22387.2 nM None
Giardia intestinalis Putative fructose-1,6-bisphosphate aldolase Potency 500.0 nM None
Giardia intestinalis Putative fructose-1,6-bisphosphate aldolase Potency 3162.3 nM None
Giardia intestinalis Putative fructose-1,6-bisphosphate aldolase Potency 12589.3 nM None
Homo sapiens A549 IC50 22.0 nM 10.1016/j.bmc.2019.115128
Homo sapiens Adenomatous polyposis coli protein/Transcription factor 7-like 2 Ki 66000.0 nM 10.1021/ml300367f
Homo sapiens Adenomatous polyposis coli protein/Transcription factor 7-like 2 Ki 170000.0 nM 10.1021/ml300367f
Homo sapiens Aldehyde dehydrogenase 1A1 Potency 39810.7 nM None
Homo sapiens Ataxin-2 Potency 4466.8 nM None
Homo sapiens ATPase family AAA domain-containing protein 5 Potency 6513.1 nM None
Homo sapiens ATP-dependent DNA helicase Q1 Potency 5011.9 nM None
Homo sapiens Bloom syndrome protein Potency 1122.0 nM None
Homo sapiens Cadherin-1/Transcription factor 7-like 2 Ki 13000.0 nM 10.1021/ml300367f
Homo sapiens Cadherin-1/Transcription factor 7-like 2 Ki 20000.0 nM 10.1021/ml300367f
Homo sapiens Caspase-1 Potency 1122.0 nM None
Homo sapiens Caspase-1 Potency 1995.3 nM None
Homo sapiens Caspase-1 Potency 3981.1 nM None
Homo sapiens Caspase-1 Potency 12589.3 nM None
Homo sapiens Caspase-7 Potency 1000.0 nM None
Homo sapiens Caspase-7 Potency 3981.1 nM None
Homo sapiens Caspase-7 Potency 6309.6 nM None
Homo sapiens Catenin beta-1 Delta Tm -0.5 degrees C 10.1021/acs.jmedchem.2c00228
Homo sapiens Catenin beta-1 IC50 10000.0 nM 10.1016/j.bmc.2013.02.050
Homo sapiens Catenin beta-1 IC50 30000.0 nM 10.1021/acs.jmedchem.5b00223
Homo sapiens Catenin beta-1 IC50 34000.0 nM 10.1021/acs.jmedchem.5b00223
Homo sapiens Catenin beta-1 IC50 340000.0 nM 10.1021/acs.jmedchem.5b00223
Homo sapiens Catenin beta-1 Ki 3650.0 nM None
Homo sapiens Catenin beta-1 Ki 3800.0 nM 10.1021/acs.jmedchem.5b00223
Homo sapiens Catenin beta-1 Ki 5800.0 nM 10.1021/acs.jmedchem.5b00223
Homo sapiens Catenin beta-1 Ki 5820.0 nM None
Homo sapiens Cellular tumor antigen p53 Potency 794.3 nM None
Homo sapiens Cellular tumor antigen p53 Potency 5011.9 nM None
Homo sapiens Cellular tumor antigen p53 Potency 79432.8 nM None
Homo sapiens Chromobox protein homolog 1 Potency 89125.1 nM None
Homo sapiens DLD-1 Inhibition nan % 10.1016/j.bmcl.2013.08.111
Homo sapiens DNA-(apurinic or apyrimidinic site) lyase Potency 44668.4 nM None
Homo sapiens DNA polymerase beta Potency 89125.1 nM None
Homo sapiens DNA polymerase eta Potency 707.9 nM None
Homo sapiens DNA polymerase eta Potency 5358.2 nM None
Homo sapiens DNA polymerase iota Potency 5323.3 nM None
Homo sapiens DNA repair and recombination protein RAD54-like AC50 1100.0 nM None
Homo sapiens Dual specificity protein phosphatase 3 IC50 980.0 nM None
Homo sapiens Dual specificity protein phosphatase 3 IC50 1360.0 nM None
Homo sapiens Eyes absent homolog 2 Potency 19952.6 nM None
Homo sapiens Eyes absent homolog 2 Potency 1463068.7 nM None
Homo sapiens Galactokinase Potency 1058.2 nM None
Homo sapiens Geminin Potency 18356.4 nM None
Homo sapiens Glucagon-like peptide 1 receptor Potency 2818.4 nM None
Homo sapiens Glyceraldehyde-3-phosphate dehydrogenase liver Potency 2511.9 nM None
Homo sapiens Guanine nucleotide-binding protein G(s), subunit alpha Potency 10000.0 nM None
Homo sapiens HCT-116 IC50 2860.0 nM 10.1016/j.ejmech.2020.113149
Homo sapiens Heat shock protein HSP90 IC50 238.1 nM None
Homo sapiens Heat shock protein HSP90 IC50 1875.0 nM None
Homo sapiens Hematopoietic cell protein-tyrosine phosphatase 70Z-PEP IC50 1240.0 nM None
Homo sapiens Hematopoietic cell protein-tyrosine phosphatase 70Z-PEP IC50 1350.0 nM None
Homo sapiens HepG2 IC50 4500.0 nM 10.1016/j.bmc.2019.115128
Homo sapiens HepG2 IC50 relative 200.0 nM 10.6019/EOS300108
Homo sapiens HepG2 Potency 199.5 nM None
Homo sapiens Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 Potency 12589.3 nM None
Homo sapiens Histone-lysine N-methyltransferase MLL Potency 10000.0 nM None
Homo sapiens Huh-7 CC50 198.6 nM 10.1073/pnas.0802982105
Homo sapiens Huntingtin Potency 5011.9 nM None
Homo sapiens Isocitrate dehydrogenase [NADP] cytoplasmic Potency 517.4 nM None
Homo sapiens Lysine-specific demethylase 4A AC50 2541.0 nM None
Homo sapiens Lysine-specific demethylase 4A IC50 2500.0 nM 10.1016/j.bmc.2019.115128
Homo sapiens Lysine-specific demethylase 4A IC50 2500.0 nM 10.1021/acs.jmedchem.2c00680
Homo sapiens Lysine-specific demethylase 4C AC50 541.4 nM None
Homo sapiens Lysine-specific demethylase 4C IC50 500.0 nM 10.1016/j.bmc.2019.115128
Homo sapiens Lysine-specific demethylase 4C IC50 541.0 nM 10.1016/j.bmc.2019.115128
Homo sapiens Lysine-specific demethylase 4D-like Potency 3981.1 nM None
Homo sapiens microRNA 21 Potency 5847.9 nM None
Homo sapiens Microtubule-associated protein tau Potency 11220.2 nM None
Homo sapiens Mothers against decapentaplegic homolog 3 Potency 112.2 nM None
Homo sapiens Muscleblind-like protein 1 Potency 2238.7 nM None
Homo sapiens NAD-dependent deacetylase sirtuin 1 IC50 870.0 nM 10.1016/j.ejmech.2016.04.063
Homo sapiens NAD-dependent deacetylase sirtuin 2 IC50 14400.0 nM 10.1016/j.ejmech.2016.04.063
Homo sapiens Neuropeptide S receptor Potency 0.3 nM None
Homo sapiens Neuropeptide S receptor Potency 1000.0 nM None
Homo sapiens Niemann-Pick C1 protein Potency 1412.5 nM None
Homo sapiens Nuclear factor erythroid 2-related factor 2 Potency 183.6 nM None
Homo sapiens Parathyroid hormone receptor Potency 766.7 nM None
Homo sapiens Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1 Potency 891.3 nM None
Homo sapiens Peroxisome proliferator-activated receptor gamma/Nuclear receptor corepressor 2 IC50 39841.0 nM None
Homo sapiens Photoreceptor-specific nuclear receptor IC50 39841.0 nM None
Homo sapiens Prelamin-A/C Potency 5011.9 nM None
Homo sapiens Protein-tyrosine phosphatase LC-PTP IC50 1240.0 nM None
Homo sapiens Rap guanine nucleotide exchange factor 3 Potency 19952.6 nM None
Homo sapiens Rap guanine nucleotide exchange factor 4 Potency 63095.7 nM None
Homo sapiens Ras and Rab interactor 1/Tyrosine-protein kinase ABL1 IC50 323.05 nM None
Homo sapiens Ras-related protein Rab-9A Potency 1122.0 nM None
Homo sapiens RKO Inhibition nan % 10.1016/j.bmcl.2013.08.111
Homo sapiens Runt-related transcription factor 1/Core-binding factor subunit beta Potency 5011.9 nM None
Homo sapiens Serine-protein kinase ATM Potency 891.3 nM None
Homo sapiens Serine/threonine-protein kinase PLK1 Potency 21192.3 nM None
Homo sapiens TAR DNA-binding protein 43 Potency 35481.3 nM None
Homo sapiens TCF4/beta-catenin Ki 3650.0 nM None
Homo sapiens TCF4/beta-catenin Ki 3700.0 nM 10.1021/ml300367f
Homo sapiens TCF4/beta-catenin Ki 5800.0 nM 10.1021/ml300367f
Homo sapiens TCF4/beta-catenin Ki 5820.0 nM None
Homo sapiens TCF4-CTNNB1 complex IC50 800.0 nM 10.1016/j.bmcl.2016.02.064
Homo sapiens Thyroid hormone receptor beta-1 Potency 100.0 nM None
Homo sapiens Thyroid stimulating hormone receptor Potency 25118.9 nM None
Homo sapiens Tyrosyl-DNA phosphodiesterase 1 Potency 206.0 nM None
Homo sapiens Tyrosyl-DNA phosphodiesterase 1 Potency 290.9 nM None
Homo sapiens Ubiquitin carboxyl-terminal hydrolase 1 Potency 31.6 nM None
Influenza A virus Nonstructural protein 1 Potency 10000.0 nM None
Mus musculus Nuclear receptor ROR-gamma Potency 39.8 nM None
Mus musculus Nuclear receptor ROR-gamma Potency 444.9 nM None
Mus musculus Nuclear receptor ROR-gamma Potency 631.0 nM None
Mus musculus Nuclear receptor ROR-gamma Potency 996.0 nM None
Mycobacterium tuberculosis Protein RecA EC50 18.0 nM None
Mycobacterium tuberculosis Protein RecA IC90 2870.0 nM None
Mycobacterium tuberculosis Replicative DNA helicase AC50 57.0 nM None
Mycobacterium tuberculosis Replicative DNA helicase AC50 83.7 nM None
Oryctolagus cuniculus Fructose-bisphosphate aldolase A Potency 4466.8 nM None
Plasmodium falciparum Plasmodium falciparum EC50 481.0 nM 10.1073/pnas.0802982105
Plasmodium falciparum Plasmodium falciparum EC50 12500.0 nM 10.1073/pnas.0802982105
Plasmodium falciparum Plasmodium falciparum Potency 928.5 nM None
Plasmodium yoelii Plasmodium yoelii Activity nan None 10.1126/science.1211936
Plasmodium yoelii Plasmodium yoelii IC50 102.8 nM 10.1126/science.1211936
Plasmodium yoelii Plasmodium yoelii Schizont size 12.53 um 10.1126/science.1211936
Rattus norvegicus Dual specificity protein phosphatase 6 IC50 2320.0 nM None
Rattus norvegicus INS1 AC50 627.0 nM None
Rattus norvegicus Thioredoxin reductase 1, cytoplasmic Potency 39810.7 nM None
Rattus norvegicus Thioredoxin reductase 1, cytoplasmic Potency 56234.1 nM None
Trypanosoma brucei brucei Phosphoglycerate kinase, glycosomal Potency 1122.0 nM None
Trypanosoma brucei brucei (strain 927/4 GUTat10.1) Phosphoglycerate kinase Potency 1456.6 nM None
Trypanosoma cruzi Cruzipain Potency 1258.9 nM None
Trypanosoma cruzi Cruzipain Potency 2238.7 nM None
None ADMET CLH 12.5 uL/min 10.1016/j.bmc.2019.115128
None ADMET permeability 16.0 10'-6 cm/s 10.1016/j.bmc.2019.115128
None ADMET Ratio 2.0 None 10.1016/j.bmc.2019.115128
None NON-PROTEIN TARGET AC50 1800.0 nM None
None NON-PROTEIN TARGET Activity nan None 10.1039/C3MD00149K
None NON-PROTEIN TARGET EC50 2100.0 nM 10.1039/C3MD00149K
None NON-PROTEIN TARGET EC50 2700.0 nM 10.1039/C3MD00149K
None NON-PROTEIN TARGET EC50 3200.0 nM 10.1039/C3MD00149K
None No relevant target EC50 1000.0 nM 10.1039/C3MD00149K
None Unchecked AC50 463.0 nM None
None Unchecked Activity nan None 10.1016/j.bmc.2019.115128
None Unchecked CC50 7979.0 nM None
None Unchecked CC50 10350.0 nM None
None Unchecked EC50 470.0 nM None
None Unchecked EC50 492.0 nM None
None Unchecked EC50 640.0 nM None
None Unchecked EC50 850.0 nM None
None Unchecked EC50 1380.0 nM None
None Unchecked IC50 290.0 nM 10.1016/j.bmcl.2013.08.111
None Unchecked IC50 330.0 nM 10.1016/j.bmcl.2013.08.111
None Unchecked IC50 510.0 nM None
None Unchecked IC50 741.0 nM None
None Unchecked IC50 1110.0 nM None
None Unchecked IC50 1290.0 nM None
None Unchecked IC50 1660.0 nM None
None Unchecked IC50 2000.0 nM None
None Unchecked IC50 2530.0 nM None
None Unchecked IC50 2840.0 nM None
None Unchecked IC50 2850.0 nM None
None Unchecked IC50 67549.0 nM None
None Unchecked IFI 26.67 % 10.1073/pnas.0802982105
None Unchecked Ki 13300.0 nM None
None Unchecked Ki 19940.0 nM None
None Unchecked Ki 66230.0 nM None
None Unchecked Ki 171250.0 nM None
None Unchecked Potency 461.1 nM None
None Unchecked Potency 501.2 nM None
None Unchecked Potency 578.0 nM None
None Unchecked Potency 595.1 nM None
None Unchecked Potency 1032.3 nM None
None Unchecked Potency 1122.0 nM None
None Unchecked Potency 1584.9 nM None
None Unchecked Potency 3149.5 nM None
None Unchecked Potency 3548.1 nM None
None Unchecked Potency 3981.1 nM None
None Unchecked Potency 12995.3 nM None
None Unchecked Ratio IC50 5.0 None 10.1016/j.bmc.2019.115128
None Unchecked Ratio Ki 2.2 None 10.1021/ml300367f
None Unchecked Ratio Ki 5.4 None 10.1021/ml300367f
None Unchecked Ratio Ki 17.8 None 10.1021/ml300367f
None Unchecked Ratio Ki 29.3 None 10.1021/ml300367f

Metabolism Information

AKRT ID Reaction Reaction Link ID
AKRT014614 C[SAH].Cn1c(=O)[nH]c2nncnc2c1=O>>Cn1ncnc2c(=O)n(C)c(=O)nc1-2 RXN-19529
AKRT015562 Cn1ncnc2c(=O)n(C)c(=O)nc1-2>>CN1N=CNc2c1[nH]c(=O)n(C)c2=O RXN-19527