Details of Metabolite

General Information of MET (ID: META00709)
Name Dihomo-alpha-linolenic acid
Synonyms   Click to Show/Hide Synonyms of This Metabolite
(11Z,14Z,17Z)-Eicosa-11,14,17-trienoate; (11Z,14Z,17Z)-Eicosa-11,14,17-trienoic acid; (11Z,14Z,17Z)-Icosa-11,14,17-trienoate; (11Z,14Z,17Z)-Icosa-11,14,17-trienoic acid; (Z,Z,Z)-11,14,17-Eicosatrienoate; (Z,Z,Z)-11,14,17-Eicosatrienoic acid; 11,14,17-Eicosatrienoate; 11,14,17-Eicosatrienoic acid; 11,14,17-Eicosatrienoic acid, (Z,Z,Z)-isomer; 11,14,17-Icosatrienoate; 11,14,17-Icosatrienoic acid; 11C,14C,17C-Eicosatrienoate; 11C,14C,17C-Eicosatrienoic acid; 11C,14C,17C-Eicosatriensaeure; 20:3, N-3,6,9 all-cis; Bishomo-a-linolenate; Bishomo-a-linolenic acid; Bishomo-alpha-linolenic acid; C20:3, N-3,6,9 all-cis; Dihomo-a-linolenate; Dihomo-a-linolenic acid; Dihomo-alpha-linolenic acid; Dihomo-linolenate; Dihomo-linolenic acid; Dihomolinolenate; Dihomolinolenic acid; ETA; ETE; Eicosa-11Z,14Z,17Z-trienoate; Eicosa-11Z,14Z,17Z-trienoic acid; Eicosatrienoate; Eicosatrienoic acid; FA(20:3(11Z,14Z,17Z)); FA(20:3n3); all-cis-11,14,17-Eicosatrienoate; all-cis-11,14,17-Eicosatrienoic acid; all-cis-Eicosa-11,14,17-trienoate; all-cis-Eicosa-11,14,17-trienoic acid; all-cis-Eicosa-11,14,17-triensaeure; cis,cis,cis-11,14,17-Eicosatrienoate; cis,cis,cis-11,14,17-Eicosatrienoic 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
5312529
HMDB ID
HMDB0060039
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
KEGG ID
C16522
ChEBI ID
53460
FooDB ID
FDB006293
ChemSpider ID
4471954
Physicochemical Properties Molecular Weight 306.5 Topological Polar Surface Area 37.3
XlogP 6.9 Complexity 327
Heavy Atom Count 22 Rotatable Bond Count 15
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 2
Function
Dihomo-alpha-linolenic acid, also known as 11,14,17-eicosatrienoic acid, is a rare polyunsaturated fatty acid of the omega-3 series. In normal humans, it represents less than 0.25% of serum phospholipid fatty acids. However, it is one of the most active essential fatty acids when assayed for the inhibition of fatty acid elongation/desaturation reactions which convert dietary C-18 fatty acids to C-20 eicosanoid precursors. (http://www.caymanchem.com)
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 Dihomo-alpha-linolenic acid concentration: increase (FC = 3.68)
                      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 dihomo-alpha-linolenic 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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