Details of Metabolite

General Information of MET (ID: META00334)
Name Stearoylcarnitine
Synonyms   Click to Show/Hide Synonyms of This Metabolite
(-)-Stearoylcarnitine; (R)-3-Carboxy-N,N,N-trimethyl-2-[(1-oxooctadecyl)oxy]-1-propanaminium inner salt; (R)-Octadecanoylcarnitine; (R)-Stearoylcarnitine; 3-(Octadecanoyloxy)-4-(trimethylammonio)butanoate; 3-(Octadecanoyloxy)-4-(trimethylammonio)butanoic acid; Acylcarnitine C18:0; L-(3-Carboxy-2-hydroxypropyl)trimethyl-ammonium stearate hydroxide inner salt; L-Stearic acid ester with (3-carboxy-2-hydroxypropyl)trimethylammonium hydroxide inner salt; L-Stearoylcarnitine; O-Octadecanoyl-(R)-carnitine; O-Octadecanoyl-R-carnitine; O-Octadecanoylcarnitine; O-Stearoyl-L-carnitine; Octadecanoyl-L-carnitine; Octadecanoylcarnitine; Stearoyl-L-carnitine; Stearoylcarnitine
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
52922056
HMDB ID
HMDB0000848
Formula
C25H49NO4
Structure
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3D MOL is unavailable 2D MOL
  Click to Show/Hide the Molecular/Functional Data (External Links/Property/Function) of This Metabolite
ChEBI ID
84644
FooDB ID
FDB022278
METLIN ID
5811
Physicochemical Properties Molecular Weight 427.7 Topological Polar Surface Area 66.4
XlogP 8.8 Complexity 426
Heavy Atom Count 30 Rotatable Bond Count 21
Hydrogen Bond Donor Count N.A. Hydrogen Bond Acceptor Count 4
Function
Stearoylcarnitine, also known as acylcarnitine C18:0, is a fatty ester lipid molecule. It is found in significantly greater amounts of patients with carnitine palmitoyltransferase (CPT) II deficiency when compared to controls. Stearoylcarnitine is also found to be associated with celiac disease, another inborn error of metabolism. The carnitine palmitoyltransferase (CPT; EC 2.3.1.21) enzyme system, in conjunction with acyl-CoA synthetase and carnitine/acylcarnitine translocase, provides the mechanism whereby long-chain fatty acids are transferred from the cytosol to the mitochondrial matrix to undergo beta-oxidation (OMIM: 600650). Stearoylcarnitine is considered to be practically insoluble (in water) and acidic.
Regulatory Network
Full List of Protein(s) Regulating This Metabolite
      Oxidoreductases (EC 1)
            Formyltetrahydrofolate dehydrogenase (ALDH1L2) 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 of ALDH1L2
                      Induced Change Stearoylcarnitine concentration: increase (FC = 1.92)
                      Summary Introduced Variation         Induced Change 
                      Disease Status Genetic disorders of keratinisation [ICD-11: EC20]
                      Details It is reported that mutation (patients) of ALDH1L2 leads to the increase of stearoylcarnitine levels compared with control group.
      Pore-forming PNC peptide (PNC)
            Cellular tumor antigen p53 (TP53) 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 [2]
                      Introduced Variation Knockout of TP53
                      Induced Change Stearoylcarnitine concentration: decrease (Log2 FC=0.73)
                      Summary Introduced Variation         Induced Change 
                      Disease Status Colon cancer [ICD-11: 2B90]
                      Details It is reported that knockout of TP53 leads to the decrease of stearoylcarnitine levels compared with control group.
References
1 Deleterious mutations in ALDH1L2 suggest a novel cause for neuro-ichthyotic syndrome. NPJ Genom Med. 2019 Jul 23;4:17.
2 Integrative omics analysis of p53-dependent regulation of metabolism. FEBS Lett. 2018 Feb;592(3):380-393.

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