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α-Ketoisocaproic acid
Chemical compound / From Wikipedia, the free encyclopedia
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α-Ketoisocaproic acid (α-KIC), also known as 4-methyl-2-oxovaleric acid, and its conjugate base and carboxylate, α-ketoisocaproate, are metabolic intermediates in the metabolic pathway for L-leucine.[2] Leucine is an essential amino acid, and its degradation is critical for many biological duties.[3] α-KIC is produced in one of the first steps of the pathway by branched-chain amino acid aminotransferase by transferring the amine on L-leucine onto alpha ketoglutarate, and replacing that amine with a ketone. The degradation of L-leucine in the muscle to this compound allows for the production of the amino acids alanine and glutamate as well. In the liver, α-KIC can be converted to a vast number of compounds depending on the enzymes and cofactors present, including cholesterol, acetyl-CoA, isovaleryl-CoA, and other biological molecules. Isovaleryl-CoA is the main compound synthesized from ɑ-KIC.[4][5][6] α-KIC is a key metabolite present in the urine of people with Maple syrup urine disease, along with other branched-chain amino acids.[7] Derivatives of α-KIC have been studied in humans for their ability to improve physical performance during anaerobic exercise as a supplemental bridge between short-term and long-term exercise supplements. These studies show that α-KIC does not achieve this goal without other ergogenicsupplements present as well.[8] α-KIC has also been observed to reduce skeletal muscle damage after eccentrically biased resistance exercises in people who do not usually perform those exercises.[9]
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Names | |
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IUPAC name
4-Methyl-2-oxopentanoic acid | |
Systematic IUPAC name
4-Methyl-2-oxopentanoic acid[1] | |
Other names
4-Methyl-2-oxovaleric acid 2-Ketoisocaproic acid 2-Oxo-4-methylpentanoic acid 2-Oxo-4-methylvaleric acid 2-Oxoisocaproic acid 2-Oxoleucine Isobutylglyoxylic acid Ketoleucine α-Ketoisocapronic acid α-Oxoisocaproic acid | |
Identifiers | |
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3D model (JSmol) |
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3DMet | |
1701823 | |
ChEBI | |
ChEMBL | |
ChemSpider |
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DrugBank |
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ECHA InfoCard | 100.011.304 ![]() |
EC Number |
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KEGG |
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MeSH | Alpha-ketoisocaproic+acid |
PubChem CID |
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UNII | |
UN number | 3265 |
CompTox Dashboard (EPA) |
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Properties | |
C6H10O3 | |
Molar mass | 130.143 g·mol−1 |
Density | 1.055 g cm−3 (at 20 °C) |
Melting point | 8 to 10 °C (46 to 50 °F; 281 to 283 K) |
Boiling point | 85 °C (185 °F; 358 K) at 13 mmHg |
log P | 0.133 |
Acidity (pKa) | 2.651 |
Basicity (pKb) | 11.346 |
Hazards | |
GHS labelling: | |
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Danger | |
H314 | |
P260, P264, P280, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P363, P405, P501 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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