General Information of MET (ID: META00313)
Name Hydroxyisocaproic acid
Synonyms   Click to Show/Hide Synonyms of This Metabolite
(+)-2-Hydroxyisocaproate; (+)-2-Hydroxyisocaproic acid; (+)-a-Hydroxyisocaproate; (+)-a-Hydroxyisocaproic acid; (+)-alpha-Hydroxyisocaproic acid; (2S)-2-Hydroxy-4-methylpentanoate; (2S)-2-Hydroxy-4-methylpentanoic acid; (S)-2-Hydroxy-4-methyl-pentanoate; (S)-2-Hydroxy-4-methyl-pentanoic acid; (S)-2-Hydroxyisocaproate; (S)-2-Hydroxyisocaproic acid; (S)-Leucate; (S)-Leucic acid; 2-HYDROXY-4-methyl-pentanoIC ACID; 2-HYDROXY-4-methyl-pentanoate; Hydroxy-isocaproate; Hydroxyisocaproate; L-2-Hydroxy-4-methylvalerate; L-2-Hydroxy-4-methylvaleric acid; L-2-Hydroxyisocaproate; L-2-Hydroxyisocaproic acid; L-Leucate; L-Leucic acid; L-a-Hydroxyisocaproate; L-a-Hydroxyisocaproic acid; L-alpha-Hydroxyisocaproic acid; S-2-Hydroxy-4-methylpentanoate; S-2-Hydroxy-4-methylpentanoic acid
Source Endogenous;Yeast Metabolite;Fatty acyls;Food;Microbial
Structure Type   Fatty acids and conjugates  (Click to Show/Hide the Complete Structure Type Hierarchy)
Lipids and lipid-like molecules
Fatty Acyls
Fatty acids and conjugates
PubChem CID
83697
HMDB ID
HMDB0000746
Formula
C6H12O3
Structure
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3D MOL 2D MOL
  Click to Show/Hide the Molecular/Functional Data (External Links/Property/Function) of This Metabolite
ChEBI ID
44510
FooDB ID
FDB022218
ChemSpider ID
75520
METLIN ID
5714
Physicochemical Properties Molecular Weight 132.16 Topological Polar Surface Area 57.5
XlogP 0.9 Complexity 98.5
Heavy Atom Count 9 Rotatable Bond Count 3
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 3
Function
Hydroxyisocaproic acid is an end product of leucine metabolism in human tissues such as muscle and connective tissue. It belongs to 2-hydroxycarboxylic acid group of amino acid metabolites. Hydroxyisocaproic acid functions as an nti-catabolite and is widely used in the body building community. Chronic alpha-hydroxyisocaproic acid treatment of rats has been shown to improve muscle recovery after immobilization-induced atrophy. Additionally, a 4-week hydroxyisocaproic acid supplementation of 1.5 g a day was shown to lead to increases in muscle mass during an intensive training period among soccer athletes. Hydroxyisocaproic acid has also shown some potential as a topical antibiotic. Elevated levels of 2-hydroxyisocaproic acid have been found in the urine of patients with dihydrolipoyl dehydrogenase (E3) deficiency. Hydroxyisocaproic acid is also elevated in maple syrup urine disease, a genetic disorder, and has been shown to accelerate lipid peroxidation. It may also be an indicator of oxidative stress. Hydroxyisocaproic acid has been found to be a metabolite of Lactobacillus and fungal species (http://jultika.oulu.fi/files/isbn9789526211046.pdf).
Regulatory Network
Full List of Protein(s) Regulating This Metabolite
      Apolipoprotein (Apo)
            Apolipoprotein A-II (APOA2) Click to Show/Hide the Full List of Regulating Pair(s):   1 Pair(s)
               Detailed Information Protein   Info click to show the details of this protein
               Regulating Pair Experim Info click to show the details of experiment for validating this pair [1]
                      Introduced Variation Mutation (-265T >C(rs5082)) of APOA2
                      Induced Change Hydroxyisocaproic acid concentration: decrease (FC = 0.71)
                      Summary Introduced Variation         Induced Change 
                      Disease Status Obesity [ICD-11: 5B81]
                      Details It is reported that mutation (-265T >C(rs5082)) of APOA2 leads to the decrease of hydroxyisocaproic acid levels compared with control group.
References
1 Epigenomics and metabolomics reveal the mechanism of the APOA2-saturated fat intake interaction affecting obesity. Am J Clin Nutr. 2018 Jul 1;108(1):188-200.

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