Details of Metabolite

General Information of MET (ID: META00311)
Name Isobutyryl-L-carnitine
Synonyms   Click to Show/Hide Synonyms of This Metabolite
(R)-Isobutyrylcarnitine; Iso-butyryl-L(-)-carnitin; Isobutyryl-1-carnitine; Isobutyryl-L-(-)-carnitine; Isobutyryl-L-carnitine; Isobutyryl-carnitine; Isobutyrylcarnitine; O-Isobutanoyl-(R)-carnitine; O-Isobutyryl-L-carnitine
Source Aliphatic acyclic compounds
Structure Type   Fatty acid esters  (Click to Show/Hide the Complete Structure Type Hierarchy)
Lipids and lipid-like molecules
Fatty Acyls
Fatty acid esters
PubChem CID
168379
HMDB ID
HMDB0000736
Formula
C11H21NO4
Structure
<iframe style="width: 300px; height: 300px;" frameborder="0" src="https://embed.molview.org/v1/?mode=balls&cid=168379"></iframe>
3D MOL 2D MOL
  Click to Show/Hide the Molecular/Functional Data (External Links/Property/Function) of This Metabolite
ChEBI ID
84838
FooDB ID
FDB022213
ChemSpider ID
147286
METLIN ID
5704
Physicochemical Properties Molecular Weight 231.29 Topological Polar Surface Area 66.4
XlogP 1.4 Complexity 250
Heavy Atom Count 16 Rotatable Bond Count 6
Hydrogen Bond Donor Count N.A. Hydrogen Bond Acceptor Count 4
Function
Isobutyryl-L-carnitine is a product of the acyl-CoA dehydrogenases (ACADs), which are a group of mitochondrial enzymes involved in the metabolism of fatty acids or branched-chain amino acids (OMIM: 600301). Isobutyryl-L-carnitine is a member of the class of compounds known as acyl carnitines. Acyl carnitines are organic compounds containing a fatty acid with the carboxylic acid attached to carnitine through an ester bond. Isobutyryl-L-carnitine is practically insoluble (in water) and a weakly acidic compound (based on its pKa).
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 Isobutyryl-L-carnitine concentration: decrease (FC = 0.62)
                      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 isobutyryl-L-carnitine levels compared with control group.
      Hydrolases (EC 3)
            GTPase KRas (KRAS) Click to Show/Hide the Full List of Regulating Pair(s):   2 Pair(s)
               Detailed Information Protein   Info click to show the details of this protein
               Regulating Pair (1) Experim Info click to show the details of experiment for validating this pair [2]
                      Introduced Variation Overexpression of KRAS
                      Induced Change Isobutyryl-L-carnitine concentration: decrease (FC = 0.80)
                      Summary Introduced Variation         Induced Change 
                      Disease Status Lung cancer [ICD-11: 2C25]
                      Details It is reported that overexpression of KRAS leads to the decrease of isobutyryl-L-carnitine levels compared with control group.
               Regulating Pair (2) Experim Info click to show the details of experiment for validating this pair [2]
                      Introduced Variation Overexpression of KRAS
                      Induced Change Isobutyryl-L-carnitine concentration: increase (FC = 1.45)
                      Summary Introduced Variation         Induced Change 
                      Disease Status Lung cancer [ICD-11: 2C25]
                      Details It is reported that overexpression of KRAS leads to the increase of isobutyryl-L-carnitine levels compared with control group.
            Sulfatase sulf-1 (SULF1) 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 [3]
                      Introduced Variation Knockdown (shRNA) of SULF1
                      Induced Change Isobutyryl-L-carnitine concentration: decrease (FC = 0.78 / 0.89)
                      Summary Introduced Variation         Induced Change 
                      Disease Status Ovarian cancer [ICD-11: 2C73]
                      Details It is reported that knockdown of SULF1 leads to the decrease of isobutyryl-L-carnitine 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.
2 Capturing the metabolomic diversity of KRAS mutants in non-small-cell lung cancer cells. Oncotarget. 2014 Jul 15;5(13):4722-31.
3 Erratum to: Loss of HSulf-1 promotes altered lipid metabolism in ovarian cancer. Cancer Metab. 2014 Nov 4;2:24.

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