Details
Stereochemistry | ACHIRAL |
Molecular Formula | C5H6O5 |
Molecular Weight | 146.0983 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
C(CC(=O)O)C(=O)C(=O)O
InChI
InChIKey=KPGXRSRHYNQIFN-UHFFFAOYSA-N
InChI=1S/C5H6O5/c6-3(5(9)10)1-2-4(7)8/h1-2H2,(H,7,8)(H,9,10)
Molecular Formula | C5H6O5 |
Molecular Weight | 146.0983 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
DescriptionSources: http://naturaldatabase.therapeuticresearch.com/nd/PrintVersion.aspx?id=144&AspxAutoDetectCookieSupport=1https://www.ncbi.nlm.nih.gov/pubmed/27416627 | https://www.ncbi.nlm.nih.gov/pubmed/18161514Curator's Comment:: Description was created based on several sources, including
http://www.uofmhealth.org/health-library/hn-4451004 | https://www.ncbi.nlm.nih.gov/pubmed/27326424 | https://www.ncbi.nlm.nih.gov/pubmed/26122777 | https://www.ncbi.nlm.nih.gov/pubmed/26759695 | https://www.ncbi.nlm.nih.gov/pubmed/10453328
Sources: http://naturaldatabase.therapeuticresearch.com/nd/PrintVersion.aspx?id=144&AspxAutoDetectCookieSupport=1https://www.ncbi.nlm.nih.gov/pubmed/27416627 | https://www.ncbi.nlm.nih.gov/pubmed/18161514
Curator's Comment:: Description was created based on several sources, including
http://www.uofmhealth.org/health-library/hn-4451004 | https://www.ncbi.nlm.nih.gov/pubmed/27326424 | https://www.ncbi.nlm.nih.gov/pubmed/26122777 | https://www.ncbi.nlm.nih.gov/pubmed/26759695 | https://www.ncbi.nlm.nih.gov/pubmed/10453328
α-Ketoglutaric acid (AKG) is a key intermediate in the tricarboxylic acid (TCA) cycle or Krebs cycle. It also plays an important role in preventing nitrogen overload by combining with nitrogen released within the cell. It is important for the proper metabolism of all essential amino acids and the transfer of cellular energy. In combination with L-glutamate, AKG can reduce levels of ammonia formed in the brain, muscles and kidneys, as well as help balance the body’s nitrogen chemistry and prevent nitrogen excess in body tissues and fluids. Individuals with high protein intake or gastrointestinal microbiota imbalance may benefit from supplemental AKG to help balance ammonia levels and protect tissues. AKG inhibits ATP synthase subunit β and is dependent on target of rapamycin (TOR) downstream. Inhibition by AKG leads to reduced ATP content, decreased oxygen consumption. Administration of AKG has been shown to be beneficial for proper development and function of the skeletal system during growth of young organisms, as well as in adulthood. In the form of a dietary supplement it also contributes to inhibition of osteoporosis in women. Moreover, it promotes the growth of muscle mass and accelerates wound healing. AKG has a significant impact on the morphology of the gastrointestinal tract in healthy animals and animals with damaged gastrointestinal tract mucosa. It is also a promising substance for the treatment of patients with short bowel syndrome, as it stimulates beneficial changes in intestinal morphology. In addition, was shown, that α-Ketoglutarate can scavenge hydrogen peroxide generated by ascorbate and epigallocatechin gallate in cell culture media.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL2062350 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24828042 |
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Target ID: hydrogen peroxide Sources: https://www.ncbi.nlm.nih.gov/pubmed/21281600 |
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Target ID: CHEMBL2816 |
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Target ID: P00367 Gene ID: 2746.0 Gene Symbol: GLUD1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/27326424 |
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Target ID: WP408 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27326424 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Palliative | Unknown Approved UseUnknown |
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Palliative | Unknown Approved UseUnknown |
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Palliative | Unknown Approved UseUnknown |
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Sources: https://www.ncbi.nlm.nih.gov/pubmed/10601539 http://www.webmd.com/vitamins-supplements/ingredientmono-642-ornithine%20ketoglutarate.aspx?activeingredientid=642&activeingredientname=ornithine%20ketoglutarate https://www.ncbi.nlm.nih.gov/pubmed/15465801 http://www.gjav.eu/ornithine-alpha-ketoglutarate/ https://www.ncbi.nlm.nih.gov/pubmed/10453328 |
Primary | ORNITHINE ALPHA-KETOGLUTARATE Approved UseOrnithine alpha-ketoglutarate (OKG) administration improves nutritional status in chronically malnourished (e.g., elderly) and acutely malnourished patients (especially burn and trauma patients). |
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Primary | ALPHA-KETOGLUTARATE Approved UseOrally, alpha-ketoglutarate is used for kidney disease, gastrointestinal disorders, bacterial overgrowth, intestinal toxemia, liver dysfunction, and chronic candidiasis. It is also used for improving peak athletic performance, improving amino acid metabolism in hemodialysis patients, and cataracts.
Intravenously, alpha-ketoglutarate is used for preventing ischemic injury during heart surgery, improving renal blood flow after heart surgery, and preventing muscle protein depletion after surgery or trauma. |
PubMed
Title | Date | PubMed |
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[1 (+) ornithine alpha ketoglutarate in hepatic encephalopathy]. | 1970 Jun 20 |
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Effect of ornithine alpha ketoglutarate (OAKG) on the response of brain metabolism to hypoxia in the dog. | 1978 May-Jun |
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[A controlled trial of ornithine alpha-ketoglutarate in neuro-traumatology]. | 1986 Oct |
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The use of alpha-ketoglutarate salts in clinical nutrition and metabolic care. | 1999 Jan |
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Nutritional and clinical efficacy of ornithine alpha-ketoglutarate in severe burn patients. | 1999 Oct |
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Effect of alpha-ketoglutarate and oxaloacetate on brain mitochondrial DNA damage and seizures induced by kainic acid in mice. | 2003 Jul 20 |
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Ornithine alpha-ketoglutarate as a potent precursor of arginine and nitric oxide: a new job for an old friend. | 2004 Oct |
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In vitro and in vivo evaluation of various carbonyl compounds against cyanide toxicity with particular reference to alpha-ketoglutaric acid. | 2008 |
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The absorption, tissue distribution and excretion of enteraly administered alpha-ketoglutarate in rats. | 2008 Apr |
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Artefacts in cell culture: α-Ketoglutarate can scavenge hydrogen peroxide generated by ascorbate and epigallocatechin gallate in cell culture media. | 2011 Mar 4 |
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The metabolite α-ketoglutarate extends lifespan by inhibiting ATP synthase and TOR. | 2014 Jun 19 |
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The Physiological Basis and Nutritional Function of Alpha-ketoglutarate. | 2015 |
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The biological role of a-ketoglutaric acid in physiological processes and its therapeutic potential. | 2016 Jan-Mar |
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Alpha-Ketoglutarate as a Molecule with Pleiotropic Activity: Well-Known and Novel Possibilities of Therapeutic Use. | 2017 Feb |
Sample Use Guides
In Vivo Use Guide
Sources: http://www.webmd.com/vitamins-supplements/ingredientmono-144-alpha-ketoglutarate.aspx?activeingredientid=144&activeingredientname=alpha-ketoglutarate http://www.webmd.com/vitamins-supplements/ingredientmono-642-ornithine%20ketoglutarate.aspx?activeingredientid=642&activeingredientname=ornithine%20ketoglutarate http://www.klaire.com/prod/proddetail.asp?id=V135-06 http://naturaldatabase.therapeuticresearch.com/nd/PrintVersion.aspx?id=144&AspxAutoDetectCookieSupport=1
For the healing of burn wounds: 30 grams of ornithine Alpha-ketoglutarate daily.
Alpha-ketoglutarate (300 mg) 1 capsule daily.
Alpha-ketoglutarate ORAL: For improving amino acid metabolism in hemodialysis patients, 1.187 grams are typically used three times daily.
For improving athletic performance 0.2 grams/kg/day of a specific alpha-ketoglutarate supplement (Evonik Rexim SAS, France) has been used.
Alpha-ketoglutarate INTRAVENOUS: For cardiac surgery, a dose of 28 grams of alpha-ketoglutarate has been added to blood cardioplegia. For preventing muscle protein depletion after surgery or trauma, 280 mg/kg of body weight is added to parenteral nutrition.
Route of Administration:
Other
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/12749815
In vitro exposure of kainic acid (0.25, 0.5 or 1.0 mM) to brain homogenate inflicted damage to mtDNA in a concentration-dependent manner. The damage of mtDNA induced by 1.0 mM kainic acid was attenuated by the co-treatment with alpha-ketoglutarate (2.5 or 5.0 mM)
Substance Class |
Chemical
Created
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Record UNII |
8ID597Z82X
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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JECFA EVALUATION |
2-OXOPENTANEDIOIC ACID
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LOINC |
27271-6
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29507-1
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13678-8
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LOINC |
21040-1
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DSLD |
1052 (Number of products:129)
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LOINC |
69802-7
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69803-5
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1817-6
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4207
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328-50-7
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C1505
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CONCEPT | Dietary Supplement | ||
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DB08845
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206-330-3
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328-50-7
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ALPHA-KETOGLUTARIC ACID
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M6620
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PRIMARY | Merck Index | ||
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17511
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PRIMARY | RxNorm | ||
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C83527
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8ID597Z82X
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SUB36364
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ACTIVE MOIETY |