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| Other Sizes |
| Targets |
3-Oxopentanedioic acid does not have a well-defined pharmacological target in the traditional sense of a drug target. As a metabolic intermediate, it is involved in various biochemical pathways, including the synthesis of tropinone and the tricarboxylic acid (TCA) cycle. It is known to be anaplerotic, meaning it can refill the pool of TCA cycle intermediates. Research indicates that the compound can inhibit enzymes involved in cellular processes, particularly TET2, which is crucial for DNA demethylation and gene regulation. Its mechanism in biological systems often involves decarboxylation to succinic semialdehyde.
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| ln Vitro |
In vitro studies have shown that 3-oxopentanedioic acid can inhibit enzymes involved in cellular processes, particularly TET2, which plays a critical role in DNA demethylation and gene regulation. Researchers utilize the compound to study enzyme mechanisms, particularly those of decarboxylases and transferases. As a metabolic intermediate, its biological activity is primarily related to its role in intermediary metabolism rather than direct pharmacological effects. The compound is also used as a substrate in enzymatic assays to study decarboxylation and condensation reactions.
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| ln Vivo |
In vivo, 3-oxopentanedioic acid functions as a metabolic intermediate involved in the TCA cycle and nitrogen metabolism. It is essential in nitrogen metabolism and serves as a precursor for glutamate and glutamine. In biomedical research, it is studied for its antioxidant properties, anti-aging potential, and role in metabolic regulation. The compound's anaplerotic role allows it to refill the pool of TCA cycle intermediates, supporting cellular energy metabolism. It also finds use in nutritional supplements and biochemical assays related to mitochondrial function.
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| Enzyme Assay |
The in vitro enzyme assay for 3-oxopentanedioic acid typically involves studying decarboxylase or transferase enzymes that use the compound as a substrate. The assay is conducted by incubating the enzyme with 3-oxopentanedioic acid (typically 0.1-10 mM) in appropriate buffer systems at optimal pH and temperature. The reaction progress is monitored by measuring the formation of products (e.g., CO2 release for decarboxylases or product formation for transferases) using spectrophotometric, fluorometric, or chromatographic methods. For TET2 inhibition studies, the compound is incubated with TET2 enzyme and DNA substrates, and the extent of DNA demethylation is measured by mass spectrometry or ELISA-based methods.
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| Cell Assay |
In vitro cellular assays for 3-oxopentanedioic acid are typically conducted using cell lines to study metabolic effects and enzyme inhibition. Cells are treated with varying concentrations of the compound (typically 0.1-10 mM) for 24-72 hours. Cellular metabolism is assessed by measuring TCA cycle intermediates, ATP levels, and oxygen consumption rate (OCR) using Seahorse or similar metabolic analyzers. For TET2 inhibition studies, DNA methylation levels are measured by bisulfite sequencing or methylation-specific PCR. Cell viability is monitored using MTT or similar assays to ensure that observed metabolic effects are not due to cytotoxicity. Gene expression changes are analyzed by qPCR or RNA-seq.
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| Animal Protocol |
In vivo animal studies for 3-oxopentanedioic acid typically involve administration to rodents to study metabolic effects. The compound can be administered orally, intraperitoneally, or intravenously at doses ranging from 10-200 mg/kg. Metabolic parameters including blood glucose, insulin, lipid profiles, and TCA cycle intermediates are measured in plasma and tissues. Mitochondrial function in tissues such as liver and muscle is assessed by measuring ATP levels and enzyme activities. The compound's effects on body weight, food intake, and metabolic rate may also be monitored. Its role in nitrogen metabolism and as a precursor for glutamate and glutamine can be studied by measuring amino acid levels in plasma and tissues.
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| ADME/Pharmacokinetics |
Pharmacokinetic properties of 3-oxopentanedioic acid are characteristic of a small dicarboxylic acid. The compound has a molecular weight of 132.07 (C5H6O5) and appears as a white to off-white powder. It has a melting point of 133degC (dec.) and a density of 400 kg/m3. As a polar, water-soluble compound, it is expected to have good aqueous solubility and limited membrane permeability. The compound is likely to be rapidly metabolized in the TCA cycle and eliminated as CO2 and water. Detailed ADME parameters such as half-life, bioavailability, and protein binding are not extensively documented in the available literature.
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| Toxicity/Toxicokinetics |
The toxicological profile of 3-oxopentanedioic acid is generally considered to be low, as it is an endogenous metabolite involved in normal cellular metabolism. As a dicarboxylic acid, high doses may cause local irritation and metabolic disturbances. The compound is used as an intermediate in organic chemical synthesis and as a research tool. It is also used in nutritional supplements and biochemical assays. No specific LD50 values or detailed toxicity profiles have been reported in the available literature. Standard safety precautions should be followed when handling the compound, including the use of appropriate personal protective equipment.
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| References | |
| Additional Infomation |
3-Ketoglutaric acid is a ketocarboxylic acid.
3-Oxopentanedioic acid (CAS 542-05-2) is also known as 1,3-acetonedicarboxylic acid, 3-oxoglutaric acid, and beta-ketoglutaric acid. It is a simple dicarboxylic acid that serves as a mandatory beta-keto dicarboxylic acid enabling the construction of 1,5-benzodiazepine cores for anxiolytic/anticonvulsant drug candidates. The compound is an endogenous metabolite and a microbial metabolite. It is involved in the synthesis of tropinone and is anaplerotic, refilling the pool of TCA cycle intermediates. It also finds use in nutritional supplements and biochemical assays related to mitochondrial function. |
| Molecular Formula |
C5H6O5
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|---|---|
| Molecular Weight |
146.09814
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| Exact Mass |
146.021
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| CAS # |
542-05-2
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| PubChem CID |
68328
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| Appearance |
White to off-white solid powder
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| Density |
1.5±0.1 g/cm3
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| Boiling Point |
408.4±30.0 °C at 760 mmHg
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| Melting Point |
133 °C (dec.)(lit.)
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| Flash Point |
214.9±21.1 °C
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| Vapour Pressure |
0.0±2.0 mmHg at 25°C
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| Index of Refraction |
1.494
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| LogP |
-1.13
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| Hydrogen Bond Donor Count |
2
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| Hydrogen Bond Acceptor Count |
5
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| Rotatable Bond Count |
4
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| Heavy Atom Count |
10
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| Complexity |
153
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| Defined Atom Stereocenter Count |
0
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| InChi Key |
OXTNCQMOKLOUAM-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C5H6O5/c6-3(1-4(7)8)2-5(9)10/h1-2H2,(H,7,8)(H,9,10)
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| Chemical Name |
3-oxopentanedioic acid
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: (1). This product is not stable in solution, please use freshly prepared working solution for optimal results. (2). Please store this product in a sealed and protected environment, avoid exposure to moisture. |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO : ~120 mg/mL (~821.36 mM)
H2O : < 0.1 mg/mL |
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 3 mg/mL (20.53 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 30.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 3 mg/mL (20.53 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 30.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. View More
Solubility in Formulation 3: ≥ 3 mg/mL (20.53 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 6.8446 mL | 34.2231 mL | 68.4463 mL | |
| 5 mM | 1.3689 mL | 6.8446 mL | 13.6893 mL | |
| 10 mM | 0.6845 mL | 3.4223 mL | 6.8446 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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