Details of Metabolite

General Information of MET (ID: META00552)
Name Oleoylcarnitine
Synonyms   Click to Show/Hide Synonyms of This Metabolite
(9Z)-Octadec-9-enoylcarnitine; (9Z)-Octadecenoyl-L-carnitine; (R)-Oleoylcarnitine; (R)-[(9Z)-Octadecenoyl]carnitine; (Z)-(+-)-3-Carboxy-N,N,N-trimethyl-2-((1-oxo-9-octadecenyl)oxy)-1-propanaminium; Acylcarnitine C18:1; O-(9Z)-Octadecenoyl-(R)-carnitine; O-Oleoylcarnitine; Oleoyl-L-carnitine; Oleoylcarnitine; Oleoylcarnitine, (R-(Z))-isomer; cis-9-Octadecenoylcarnitine
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
46907933
HMDB ID
HMDB0005065
Formula
C25H47NO4
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
84651
FooDB ID
FDB023614
ChemSpider ID
21403150
Physicochemical Properties Molecular Weight 425.6 Topological Polar Surface Area 66.4
XlogP 7.9 Complexity 463
Heavy Atom Count 30 Rotatable Bond Count 20
Hydrogen Bond Donor Count N.A. Hydrogen Bond Acceptor Count 4
Function
Oleoylcarnitine is a long-chain acylcarnitine that accumulates during certain metabolic conditions, such as fasting. Oleoylcarnitine 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 Oleoylcarnitine concentration: increase (FC = 1.28)
                      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 increase of oleoylcarnitine levels compared with control group.
      Hydrolases (EC 3)
            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 [2]
                      Introduced Variation Knockdown (shRNA) of SULF1
                      Induced Change Oleoylcarnitine concentration: increase (FC = 6.64 - 16.84)
                      Summary Introduced Variation         Induced Change 
                      Disease Status Ovarian cancer [ICD-11: 2C73]
                      Details It is reported that knockdown of SULF1 leads to the increase of oleoylcarnitine levels compared with control group.
      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 [3]
                      Introduced Variation Mutation of ALDH1L2
                      Induced Change Oleoylcarnitine concentration: increase (FC = 4.76)
                      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 oleoylcarnitine 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 Erratum to: Loss of HSulf-1 promotes altered lipid metabolism in ovarian cancer. Cancer Metab. 2014 Nov 4;2:24.
3 Deleterious mutations in ALDH1L2 suggest a novel cause for neuro-ichthyotic syndrome. NPJ Genom Med. 2019 Jul 23;4:17.

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