Details
Stereochemistry | ACHIRAL |
Molecular Formula | C5H6O5 |
Molecular Weight | 146.0981 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
OC(=O)CCC(=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)
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/27416627 | https://www.ncbi.nlm.nih.gov/pubmed/18161514http://naturaldatabase.therapeuticresearch.com/nd/PrintVersion.aspx?id=144&AspxAutoDetectCookieSupport=1Curator'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: https://www.ncbi.nlm.nih.gov/pubmed/27416627 | https://www.ncbi.nlm.nih.gov/pubmed/18161514http://naturaldatabase.therapeuticresearch.com/nd/PrintVersion.aspx?id=144&AspxAutoDetectCookieSupport=1
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
Alpha-ketoglutarate (AKG), an endogenous intermediary metabolite in the Krebs cycle, is a molecule involved in multiple metabolic and cellular pathways. As an intermediate of the tricarboxylic acid cycle, AKG is essential for the oxidation of fatty acids, amino acids, and glucose. Extracellular AKG is a significant source of energy for cells of the gastrointestinal tract. As a precursor for the synthesis of glutamate and glutamine in multiple tissues (including liver, skeletal muscle, heart, brain, and white adipose tissue), AKG bridges carbohydrate and nitrogen metabolism for both conservation of amino acids and ammonia detoxification. Additionally, emerging evidence shows that AKG is a regulator of gene expression and cell signaling pathways (including the mammalian target of rapamycin and AMPactivated protein kinase). Thus, AKG is an attractive dietary supplement in animal and human nutrition to improve cellular energy status, immunity, and health.AKG can decrease protein catabolism and increase protein synthesis to enhance bone tissue formation in the skeletal muscles and can be used in clinical applications. In addition to these health benefits, a recent study has shown that AKG can extend the lifespan of adult Caenorhabditis elegans by inhibiting ATP synthase and TOR. Orally, AKG 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, AKG 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.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2062350 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24828042 |
|||
Target ID: hydrogen peroxide Sources: https://www.ncbi.nlm.nih.gov/pubmed/21281600 |
|||
Target ID: CHEMBL2816 |
|||
Target ID: P00367 Gene ID: 2746.0 Gene Symbol: GLUD1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/27326424 |
|||
Target ID: WP408 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27326424 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Palliative | Unknown Approved UseUnknown |
|||
Palliative | Unknown Approved UseUnknown |
|||
Palliative | Unknown Approved UseUnknown |
|||
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). |
||
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. |
Sample Use Guides
In Vivo Use Guide
Sources: http://www.klaire.com/prod/proddetail.asp?id=V135-06
1 capsule daily
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/18161514
It was investigated the efficacy of several carbonyl compounds and their metabolites or nutrients with alpha-ketoglutaric acid (A-KG), citric acid, succinic acid, maleic acid, malic acid, fumaric and oxaloacetic acid, glucose, sucrose, fructose, mannitol, sorbitol, dihydroxyacetone, and glyoxal (5 or 10 mM; -10 min) against toxicity of potassium cyanide (KCN; 10 mM) in rat thymocytes in vitro. Six hours after KCN, cell viability measured by MTT assay and crystal violet dye exclusion revealed maximum cytoprotection by A-KG, followed by oxaloacetic acid. A-KG also resolved the leakage of intracellular lactate dehydrogenase, loss in nuclear integrity (propidium iodide staining), and altered mitochondrial membrane potential (rhodamine 123 assay) as a result of cyanide toxicity. Protection Index (ratio of LD(50) of KCN in protected and unprotected animals; PI) of all the compounds (oral; 1.0 g/kg; -10 min) determined in male mice, revealed that maximum protection was afforded by A-KG (7.6 PI), followed by oxaloacetic acid (6.4 PI). Comparative evaluation of various salts of A-KG alone or with STS (intraperitoneal; 1.0 g/kg; -15 min) showed that maximum protection was conferred by disodium anhydrous salt of A-KG, which also significantly prevented the inhibition of brain cytochrome oxidase caused by 0.75 LD(50) KCN.
Name | Type | Language | ||
---|---|---|---|---|
|
Common Name | English | ||
|
Preferred Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Official Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Official Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English |
Classification Tree | Code System | Code | ||
---|---|---|---|---|
|
JECFA EVALUATION |
2-OXOPENTANEDIOIC ACID
Created by
admin on Fri Dec 15 15:10:43 GMT 2023 , Edited by admin on Fri Dec 15 15:10:43 GMT 2023
|
||
|
LOINC |
27271-6
Created by
admin on Fri Dec 15 15:10:43 GMT 2023 , Edited by admin on Fri Dec 15 15:10:43 GMT 2023
|
||
|
LOINC |
29507-1
Created by
admin on Fri Dec 15 15:10:43 GMT 2023 , Edited by admin on Fri Dec 15 15:10:43 GMT 2023
|
||
|
LOINC |
13678-8
Created by
admin on Fri Dec 15 15:10:43 GMT 2023 , Edited by admin on Fri Dec 15 15:10:43 GMT 2023
|
||
|
LOINC |
21040-1
Created by
admin on Fri Dec 15 15:10:43 GMT 2023 , Edited by admin on Fri Dec 15 15:10:43 GMT 2023
|
||
|
DSLD |
1052 (Number of products:129)
Created by
admin on Fri Dec 15 15:10:43 GMT 2023 , Edited by admin on Fri Dec 15 15:10:43 GMT 2023
|
||
|
LOINC |
69802-7
Created by
admin on Fri Dec 15 15:10:43 GMT 2023 , Edited by admin on Fri Dec 15 15:10:43 GMT 2023
|
||
|
LOINC |
69803-5
Created by
admin on Fri Dec 15 15:10:43 GMT 2023 , Edited by admin on Fri Dec 15 15:10:43 GMT 2023
|
||
|
LOINC |
1817-6
Created by
admin on Fri Dec 15 15:10:43 GMT 2023 , Edited by admin on Fri Dec 15 15:10:43 GMT 2023
|
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
100000128818
Created by
admin on Fri Dec 15 15:10:43 GMT 2023 , Edited by admin on Fri Dec 15 15:10:43 GMT 2023
|
PRIMARY | |||
|
17391
Created by
admin on Fri Dec 15 15:10:43 GMT 2023 , Edited by admin on Fri Dec 15 15:10:43 GMT 2023
|
PRIMARY | |||
|
455
Created by
admin on Fri Dec 15 15:10:43 GMT 2023 , Edited by admin on Fri Dec 15 15:10:43 GMT 2023
|
PRIMARY | |||
|
4207
Created by
admin on Fri Dec 15 15:10:43 GMT 2023 , Edited by admin on Fri Dec 15 15:10:43 GMT 2023
|
PRIMARY | |||
|
DTXSID5033179
Created by
admin on Fri Dec 15 15:10:43 GMT 2023 , Edited by admin on Fri Dec 15 15:10:43 GMT 2023
|
PRIMARY | |||
|
8ID597Z82X
Created by
admin on Fri Dec 15 15:10:43 GMT 2023 , Edited by admin on Fri Dec 15 15:10:43 GMT 2023
|
PRIMARY | |||
|
C1505
Created by
admin on Fri Dec 15 15:10:43 GMT 2023 , Edited by admin on Fri Dec 15 15:10:43 GMT 2023
|
CONCEPT | Dietary Supplement | ||
|
30915
Created by
admin on Fri Dec 15 15:10:43 GMT 2023 , Edited by admin on Fri Dec 15 15:10:43 GMT 2023
|
PRIMARY | |||
|
DB08845
Created by
admin on Fri Dec 15 15:10:43 GMT 2023 , Edited by admin on Fri Dec 15 15:10:43 GMT 2023
|
PRIMARY | |||
|
51
Created by
admin on Fri Dec 15 15:10:43 GMT 2023 , Edited by admin on Fri Dec 15 15:10:43 GMT 2023
|
PRIMARY | |||
|
206-330-3
Created by
admin on Fri Dec 15 15:10:43 GMT 2023 , Edited by admin on Fri Dec 15 15:10:43 GMT 2023
|
PRIMARY | |||
|
328-50-7
Created by
admin on Fri Dec 15 15:10:42 GMT 2023 , Edited by admin on Fri Dec 15 15:10:42 GMT 2023
|
PRIMARY | |||
|
ALPHA-KETOGLUTARIC ACID
Created by
admin on Fri Dec 15 15:10:43 GMT 2023 , Edited by admin on Fri Dec 15 15:10:43 GMT 2023
|
PRIMARY | |||
|
m6620
Created by
admin on Fri Dec 15 15:10:43 GMT 2023 , Edited by admin on Fri Dec 15 15:10:43 GMT 2023
|
PRIMARY | Merck Index | ||
|
17511
Created by
admin on Fri Dec 15 15:10:43 GMT 2023 , Edited by admin on Fri Dec 15 15:10:43 GMT 2023
|
PRIMARY | RxNorm | ||
|
C83527
Created by
admin on Fri Dec 15 15:10:43 GMT 2023 , Edited by admin on Fri Dec 15 15:10:43 GMT 2023
|
PRIMARY | |||
|
8ID597Z82X
Created by
admin on Fri Dec 15 15:10:43 GMT 2023 , Edited by admin on Fri Dec 15 15:10:43 GMT 2023
|
PRIMARY | |||
|
SUB36364
Created by
admin on Fri Dec 15 15:10:42 GMT 2023 , Edited by admin on Fri Dec 15 15:10:42 GMT 2023
|
PRIMARY | |||
|
16810
Created by
admin on Fri Dec 15 15:10:43 GMT 2023 , Edited by admin on Fri Dec 15 15:10:43 GMT 2023
|
PRIMARY |
ACTIVE MOIETY
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)