Details of Metabolite

General Information of MET (ID: META00585)
Name 5,8,11-Eicosatrienoic acid
Synonyms   Click to Show/Hide Synonyms of This Metabolite
(5Z,8Z,11Z)-Eicosa-5,8,11-trienoate; (5Z,8Z,11Z)-Eicosa-5,8,11-trienoic acid; (5Z,8Z,11Z)-Eicosatrienoate; (5Z,8Z,11Z)-Eicosatrienoic acid; (5Z,8Z,11Z)-Icosatrienoate; 5,8,11-Eicosatrienoate; 5,8,11-Eicosatrienoic acid; 5Z,8Z,11Z-Eicosatrienoate; 5Z,8Z,11Z-Eicosatrienoic acid; 5Z,8Z,11Z-Icosatrienoate; 5Z,8Z,11Z-Icosatrienoic acid; C20:3N-9,12,15; ETrA acid; ETrE(5Z,8Z,11Z); Mead acid; all-cis-Eicosa-5,8,11-trienoate; all-cis-Eicosa-5,8,11-trienoic acid; all-cis-Icosa-5,8,11-trienoate; all-cis-Icosa-5,8,11-trienoic 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
5312531
HMDB ID
HMDB0010378
Formula
C20H34O2
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
72865
Physicochemical Properties Molecular Weight 306.5 Topological Polar Surface Area 37.3
XlogP 7 Complexity 327
Heavy Atom Count 22 Rotatable Bond Count 15
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 2
Function
5,8,11-Eicosatrienoic acid (Mead acid) is a carboxylic acid with a 20-carbon chain and three methylene-interrupted cis double bonds. The first double bond is located at the ninth carbon from the omega end. In physiological literature, it is given the name 20:3(n-9). In the presence of lipoxygenase, Mead acid can form various hydroxy products (HETE). It is the only polyunsaturated fatty acid that the body can make de novo. Its elevated presence in the blood is an indication of essential fatty acid (EFA)deficiency. During dietary EFA insufficiency, especially arachidonic acid deficiency, the body will make Mead acid by the elongation and desaturation of oleic acid.
Regulatory Network
Full List of Protein(s) Regulating This Metabolite
      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 [1]
                      Introduced Variation Knockdown (shRNA) of SULF1
                      Induced Change 5,8,11-Eicosatrienoic acid concentration: decrease (FC = 0.66)
                      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 5,8,11-eicosatrienoic acid levels compared with control group.
References
1 Erratum to: Loss of HSulf-1 promotes altered lipid metabolism in ovarian cancer. Cancer Metab. 2014 Nov 4;2:24.

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