Details of Metabolite

General Information of MET (ID: META00251)
Name 2-Ethylhydracrylic acid
Synonyms   Click to Show/Hide Synonyms of This Metabolite
2-(Hydroxymethyl)-butyrate; 2-(Hydroxymethyl)-butyric acid; 2-(Hydroxymethyl)butyrate; 2-(Hydroxymethyl)butyric acid; 2-Ethyl-3-hydroxypropionate; 2-Ethyl-3-hydroxypropionic acid; 2-Ethyl-hydracrylate; 2-Ethylhydracrylate; 2-Ethylhydracrylic acid; 3-Hydroxy-2-ethylpropanoate; 3-Hydroxy-2-ethylpropanoic acid; 3-Hydroxy-2-ethylpropionate; 3-Hydroxy-2-ethylpropionic acid; 3-Hydroxy-propionic acid ethyl ester; b-Hydroxy-a-ethylpropionate; b-Hydroxy-a-ethylpropionic acid; beta-Hydroxy-alpha-ethylpropionic acid
Source Endogenous;Fatty acyls;Food
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
188979
HMDB ID
HMDB0000396
Formula
C5H10O3
Structure
<iframe style="width: 300px; height: 300px;" frameborder="0" src="https://embed.molview.org/v1/?mode=balls&cid=188979"></iframe>
3D MOL 2D MOL
  Click to Show/Hide the Molecular/Functional Data (External Links/Property/Function) of This Metabolite
ChEBI ID
82956
FooDB ID
FDB022014
ChemSpider ID
164207
METLIN ID
3785
Physicochemical Properties Molecular Weight 118.13 Topological Polar Surface Area 57.5
XlogP N.A. Complexity 79.7
Heavy Atom Count 8 Rotatable Bond Count 3
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 3
Function
Isolated excretion of 2-ethylhydracrylic acid (2-methylbutyrylglycine; 2-MBG) is the hallmark of short/branched-chain acyl-CoA dehydrogenase deficiency (SBCADD), a defect in the proximal pathway of L-isoleucine oxidation. Normal human urine contains small amounts (less than 4 mg/g of creatinine) of 2-ethylhydracrylic acid. Urinary excretion of 2-ethylhydracrylic acid is variably increased in defects of isoleucine oxidation at distal steps in the catabolic pathway (3-oxoacyl-CoA thiolase deficiency and methylmalonyl-CoA mutase deficiency) and is diminished when proximal steps of the oxidative pathway are blocked as in branched-chain oxo acid decarboxylase deficiency (maple syrup urine disease). 2-Ethylhydracrylic acid has been identified in the human placenta.
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 2-Ethylhydracrylic acid concentration: decrease (FC = 0.78)
                      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 2-ethylhydracrylic 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.

If you find any error in data or bug in web service, please kindly report it to Dr. Zhang and Dr. Mou.