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Literature summary for 2.7.1.40 extracted from
- Discovery of novel naphthoquinone derivatives as inhibitors of the tumor cell specific M2 isoform of pyruvate kinase (2017), Eur. J. Med. Chem., 138, 343-352 .
Application
| Application | Comment | Organism |
|---|---|---|
| drug development | cancer cells rely heavily on PKM2 for anabolic and energy requirements, and specific targeting of PKM2 therefore has potential as strategy for cancer therapy | Homo sapiens |
Cloned(Commentary)
| Cloned (Comment) | Organism |
|---|---|
| recombinant expression of His-tagged enzyme in Escherichia coli strain BL21 | Homo sapiens |
Inhibitors
| Inhibitors | Comment | Organism | Structure |
|---|---|---|---|
| (1,4-dimethoxynaphthalen-2-yl)methyl dipropylcarbamodithioate | - |
Homo sapiens |  |
| (1,4-dioxo-1,4-dihydronaphthalen-2-yl)methyl diethylcarbamodithioate | - |
Homo sapiens | |
| (1,4-dioxo-1,4-dihydronaphthalen-2-yl)methyl morpholine-4-carbodithioate | - |
Homo sapiens | |
| (1,4-dioxo-1,4-dihydronaphthalen-2-yl)methyl piperidine-1-carbodithioate | - |
Homo sapiens | |
| (1,4-dioxo-1,4-dihydronaphthalen-2-yl)methyl [4-(piperazin-1-yl)phenyl]carbamodithioate | - |
Homo sapiens | |
| (3-methyl-1,4-dioxo-1,4-dihydronaphthalen-2-yl)methyl (4-methylpiperidin-1-yl)carbamodithioate | - |
Homo sapiens | |
| (3-methyl-1,4-dioxo-1,4-dihydronaphthalen-2-yl)methyl 1,3-thiazolidine-3-carbodithioate | - |
Homo sapiens | |
| (3-methyl-1,4-dioxo-1,4-dihydronaphthalen-2-yl)methyl 3,5-dimethylmorpholine-4-carbodithioate | - |
Homo sapiens | |
| (3-methyl-1,4-dioxo-1,4-dihydronaphthalen-2-yl)methyl 4-(propan-2-yl)piperazine-1-carbodithioate | - |
Homo sapiens | |
| (3-methyl-1,4-dioxo-1,4-dihydronaphthalen-2-yl)methyl 4-acetylpiperazine-1-carbodithioate | - |
Homo sapiens | |
| (3-methyl-1,4-dioxo-1,4-dihydronaphthalen-2-yl)methyl 4-methylpiperazine-1-carbodithioate | - |
Homo sapiens | |
| (3-methyl-1,4-dioxo-1,4-dihydronaphthalen-2-yl)methyl benzylcarbamodithioate | - |
Homo sapiens | |
| (3-methyl-1,4-dioxo-1,4-dihydronaphthalen-2-yl)methyl bis(2-hydroxyethyl)carbamodithioate | - |
Homo sapiens | |
| (3-methyl-1,4-dioxo-1,4-dihydronaphthalen-2-yl)methyl cyclohexyl(methyl)carbamodithioate | - |
Homo sapiens | |
| (3-methyl-1,4-dioxo-1,4-dihydronaphthalen-2-yl)methyl dibutylcarbamodithioate | - |
Homo sapiens | |
| (3-methyl-1,4-dioxo-1,4-dihydronaphthalen-2-yl)methyl diethylcarbamodithioate | - |
Homo sapiens | |
| (3-methyl-1,4-dioxo-1,4-dihydronaphthalen-2-yl)methyl diprop-2-en-1-ylcarbamodithioate | - |
Homo sapiens | |
| (3-methyl-1,4-dioxo-1,4-dihydronaphthalen-2-yl)methyl dipropylcarbamodithioate | - |
Homo sapiens | |
| (3-methyl-1,4-dioxo-1,4-dihydronaphthalen-2-yl)methyl methylcarbamodithioate | - |
Homo sapiens | |
| (3-methyl-1,4-dioxo-1,4-dihydronaphthalen-2-yl)methyl morpholine-4-carbodithioate | - |
Homo sapiens | |
| (3-methyl-1,4-dioxo-1,4-dihydronaphthalen-2-yl)methyl piperidin-1-ylcarbamodithioate | - |
Homo sapiens | |
| (3-methyl-1,4-dioxo-1,4-dihydronaphthalen-2-yl)methyl piperidine-1-carbodithioate | - |
Homo sapiens | |
| (3-methyl-1,4-dioxo-1,4-dihydronaphthalen-2-yl)methyl pyrrolidine-1-carbodithioate | - |
Homo sapiens | |
| (3-methyl-1,4-dioxo-1,4-dihydronaphthalen-2-yl)methyl thiomorpholine-4-carbodithioate | - |
Homo sapiens | |
| (3-methyl-1,4-dioxo-1,4-dihydronaphthalen-2-yl)methyl [(pyridin-2-yl)methyl]carbamodithioate | - |
Homo sapiens | |
| (3-methyl-1,4-dioxo-1,4-dihydronaphthalen-2-yl)methyl [(pyridin-3-yl)methyl]carbamodithioate | - |
Homo sapiens | |
| (3-methyl-1,4-dioxo-1,4-dihydronaphthalen-2-yl)methyl [(pyridin-4-yl)methyl]carbamodithioate | - |
Homo sapiens | |
| (3-methyl-1,4-dioxo-1,4-dihydronaphthalen-2-yl)methyl [2-(diethylamino)ethyl]carbamodithioate | - |
Homo sapiens | |
| 3-methyl-1,4-dioxo-1,4-dihydronaphthalen-2-yl 4-acetylpiperazine-1-carbodithioate | - |
Homo sapiens | |
| 3-methyl-1,4-dioxo-1,4-dihydronaphthalen-2-yl dipropylcarbamodithioate | - |
Homo sapiens | |
| 3-methyl-1,4-dioxo-1,4-dihydronaphthalen-2-yl morpholine-4-carbodithioate | - |
Homo sapiens | |
| 3-methyl-1,4-dioxo-1,4-dihydronaphthalen-2-yl piperidine-1-carbodithioate | - |
Homo sapiens | |
| alkannin | - |
Homo sapiens | |
| additional information | synthesis and biologic evaluation of naphthoquinone derivatives as selective small molecule inhibitors of PKM2, cytotoxicity of the compounds versus HeLa, H-1299, and HCT-116 cancer cells, overview. Presence of fructose 1,6-bisphosphate increases the IC50 values of some inhibitors | Homo sapiens | |
| shikonin | - |
Homo sapiens | |
Metals/Ions
| Metals/Ions | Comment | Organism | Structure |
|---|---|---|---|
| Mg2+ | required | Homo sapiens | |
Natural Substrates/ Products (Substrates)
| Natural Substrates | Organism | Comment (Nat. Sub.) | Natural Products | Comment (Nat. Pro.) | Rev. | Reac. |
|---|---|---|---|---|---|---|
| ADP + phosphoenolpyruvate | Homo sapiens | - |
ATP + pyruvate | - |
? | |
Organism
| Organism | UniProt | Comment | Textmining |
|---|---|---|---|
| Homo sapiens | P14618 | - |
- |
Purification (Commentary)
| Purification (Comment) | Organism |
|---|---|
| recombinant His-tagged enzyme from Escherichia coli strain BL21 | Homo sapiens |
Source Tissue
| Source Tissue | Comment | Organism | Textmining |
|---|---|---|---|
| HCT-116 cell | - |
Homo sapiens | - |
| HeLa cell | - |
Homo sapiens | - |
Substrates and Products (Substrate)
| Substrates | Comment Substrates | Organism | Products | Comment (Products) | Rev. | Reac. |
|---|---|---|---|---|---|---|
| ADP + phosphoenolpyruvate | - |
Homo sapiens | ATP + pyruvate | - |
? | |
Synonyms
| Synonyms | Comment | Organism |
|---|---|---|
| PKM2 | - |
Homo sapiens |
| pyruvate kinase M2 | - |
Homo sapiens |
Temperature Optimum [°C]
| Temperature Optimum [°C] | Temperature Optimum Maximum [°C] | Comment | Organism |
|---|---|---|---|
| 37 | - |
assay at | Homo sapiens |
pH Optimum
| pH Optimum Minimum | pH Optimum Maximum | Comment | Organism |
|---|---|---|---|
| 7.5 | - |
assay at | Homo sapiens |
IC50 Value
| IC50 Value | IC50 Value Maximum | Comment | Organism | Inhibitor | Structure |
|---|---|---|---|---|---|
| 0.0014 | - |
recombinant His-tagged enzyme, pH 7.5, 37°C | Homo sapiens | (1,4-dioxo-1,4-dihydronaphthalen-2-yl)methyl [4-(piperazin-1-yl)phenyl]carbamodithioate | |
| 0.00174 | - |
recombinant His-tagged enzyme, pH 7.5, 37°C | Homo sapiens | (1,4-dioxo-1,4-dihydronaphthalen-2-yl)methyl piperidine-1-carbodithioate | |
| 0.00221 | - |
recombinant His-tagged enzyme, pH 7.5, 37°C | Homo sapiens | (3-methyl-1,4-dioxo-1,4-dihydronaphthalen-2-yl)methyl benzylcarbamodithioate | |
| 0.00258 | - |
recombinant His-tagged enzyme, pH 7.5, 37°C | Homo sapiens | (1,4-dioxo-1,4-dihydronaphthalen-2-yl)methyl diethylcarbamodithioate | |
| 0.00295 | - |
recombinant His-tagged enzyme, pH 7.5, 37°C | Homo sapiens | (3-methyl-1,4-dioxo-1,4-dihydronaphthalen-2-yl)methyl piperidine-1-carbodithioate | |
| 0.00423 | - |
recombinant His-tagged enzyme, pH 7.5, 37°C | Homo sapiens | (1,4-dioxo-1,4-dihydronaphthalen-2-yl)methyl morpholine-4-carbodithioate | |
| 0.00457 | - |
recombinant His-tagged enzyme, pH 7.5, 37°C | Homo sapiens | (3-methyl-1,4-dioxo-1,4-dihydronaphthalen-2-yl)methyl dibutylcarbamodithioate | |
| 0.00493 | - |
recombinant His-tagged enzyme, pH 7.5, 37°C | Homo sapiens | 3-methyl-1,4-dioxo-1,4-dihydronaphthalen-2-yl piperidine-1-carbodithioate | |
| 0.00508 | - |
recombinant His-tagged enzyme, pH 7.5, 37°C | Homo sapiens | (3-methyl-1,4-dioxo-1,4-dihydronaphthalen-2-yl)methyl cyclohexyl(methyl)carbamodithioate | |
| 0.00528 | - |
recombinant His-tagged enzyme, pH 7.5, 37°C | Homo sapiens | (3-methyl-1,4-dioxo-1,4-dihydronaphthalen-2-yl)methyl 1,3-thiazolidine-3-carbodithioate | |
| 0.00589 | - |
recombinant His-tagged enzyme, pH 7.5, 37°C | Homo sapiens | (3-methyl-1,4-dioxo-1,4-dihydronaphthalen-2-yl)methyl thiomorpholine-4-carbodithioate | |
| 0.00679 | - |
recombinant His-tagged enzyme, pH 7.5, 37°C | Homo sapiens | (3-methyl-1,4-dioxo-1,4-dihydronaphthalen-2-yl)methyl dipropylcarbamodithioate | |
| 0.0085 | - |
recombinant His-tagged enzyme, pH 7.5, 37°C | Homo sapiens | 3-methyl-1,4-dioxo-1,4-dihydronaphthalen-2-yl morpholine-4-carbodithioate | |
| 0.00878 | - |
recombinant His-tagged enzyme, pH 7.5, 37°C | Homo sapiens | (3-methyl-1,4-dioxo-1,4-dihydronaphthalen-2-yl)methyl diethylcarbamodithioate | |
| 0.00882 | - |
pH 7.5, 37°C | Homo sapiens | shikonin | |
| 0.00998 | - |
recombinant His-tagged enzyme, pH 7.5, 37°C | Homo sapiens | 3-methyl-1,4-dioxo-1,4-dihydronaphthalen-2-yl dipropylcarbamodithioate | |
| 0.0117 | - |
recombinant His-tagged enzyme, pH 7.5, 37°C | Homo sapiens | (3-methyl-1,4-dioxo-1,4-dihydronaphthalen-2-yl)methyl 3,5-dimethylmorpholine-4-carbodithioate | |
| 0.01411 | - |
recombinant His-tagged enzyme, pH 7.5, 37°C | Homo sapiens | (3-methyl-1,4-dioxo-1,4-dihydronaphthalen-2-yl)methyl diprop-2-en-1-ylcarbamodithioate | |
| 0.01424 | - |
recombinant His-tagged enzyme, pH 7.5, 37°C | Homo sapiens | (3-methyl-1,4-dioxo-1,4-dihydronaphthalen-2-yl)methyl 4-methylpiperazine-1-carbodithioate | |
| 0.01524 | - |
recombinant His-tagged enzyme, pH 7.5, 37°C | Homo sapiens | (3-methyl-1,4-dioxo-1,4-dihydronaphthalen-2-yl)methyl morpholine-4-carbodithioate | |
| 0.01566 | - |
recombinant His-tagged enzyme, pH 7.5, 37°C | Homo sapiens | (1,4-dimethoxynaphthalen-2-yl)methyl dipropylcarbamodithioate | |
| 0.01973 | - |
recombinant His-tagged enzyme, pH 7.5, 37°C | Homo sapiens | (3-methyl-1,4-dioxo-1,4-dihydronaphthalen-2-yl)methyl pyrrolidine-1-carbodithioate | |
| 0.02 | - |
recombinant His-tagged enzyme, pH 7.5, 37°C | Homo sapiens | (3-methyl-1,4-dioxo-1,4-dihydronaphthalen-2-yl)methyl (4-methylpiperidin-1-yl)carbamodithioate | |
| 0.02 | - |
recombinant His-tagged enzyme, pH 7.5, 37°C | Homo sapiens | (3-methyl-1,4-dioxo-1,4-dihydronaphthalen-2-yl)methyl 4-(propan-2-yl)piperazine-1-carbodithioate | |
| 0.02 | - |
recombinant His-tagged enzyme, pH 7.5, 37°C | Homo sapiens | (3-methyl-1,4-dioxo-1,4-dihydronaphthalen-2-yl)methyl 4-acetylpiperazine-1-carbodithioate | |
| 0.02 | - |
recombinant His-tagged enzyme, pH 7.5, 37°C | Homo sapiens | (3-methyl-1,4-dioxo-1,4-dihydronaphthalen-2-yl)methyl bis(2-hydroxyethyl)carbamodithioate | |
| 0.02 | - |
recombinant His-tagged enzyme, pH 7.5, 37°C | Homo sapiens | (3-methyl-1,4-dioxo-1,4-dihydronaphthalen-2-yl)methyl methylcarbamodithioate | |
| 0.02 | - |
recombinant His-tagged enzyme, pH 7.5, 37°C | Homo sapiens | (3-methyl-1,4-dioxo-1,4-dihydronaphthalen-2-yl)methyl piperidin-1-ylcarbamodithioate | |
| 0.02 | - |
recombinant His-tagged enzyme, pH 7.5, 37°C | Homo sapiens | (3-methyl-1,4-dioxo-1,4-dihydronaphthalen-2-yl)methyl [(pyridin-2-yl)methyl]carbamodithioate | |
| 0.02 | - |
recombinant His-tagged enzyme, pH 7.5, 37°C | Homo sapiens | (3-methyl-1,4-dioxo-1,4-dihydronaphthalen-2-yl)methyl [(pyridin-3-yl)methyl]carbamodithioate | |
| 0.02 | - |
recombinant His-tagged enzyme, pH 7.5, 37°C | Homo sapiens | (3-methyl-1,4-dioxo-1,4-dihydronaphthalen-2-yl)methyl [(pyridin-4-yl)methyl]carbamodithioate | |
| 0.02 | - |
recombinant His-tagged enzyme, pH 7.5, 37°C | Homo sapiens | (3-methyl-1,4-dioxo-1,4-dihydronaphthalen-2-yl)methyl [2-(diethylamino)ethyl]carbamodithioate | |
| 0.02 | - |
recombinant His-tagged enzyme, pH 7.5, 37°C | Homo sapiens | 3-methyl-1,4-dioxo-1,4-dihydronaphthalen-2-yl 4-acetylpiperazine-1-carbodithioate | |
General Information
| General Information | Comment | Organism |
|---|---|---|
| physiological function | pyruvate kinase M2 (PKM2) is a rate-limiting enzyme of the glycolytic pathway which is highly expressed in cancer cells. Cancer cells rely heavily on PKM2 for anabolic and energy requirements | Homo sapiens |
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