Details of Metabolite

General Information of MET (ID: META00569)
Name Docosapentaenoic acid (22n-3)
Synonyms   Click to Show/Hide Synonyms of This Metabolite
(7Z,10Z,13Z,16Z,19Z)-7,10,13,16,19-Docosapentaenoic acid; (7Z,10Z,13Z,16Z,19Z)-Docosa 7,10,13,16,19-pentaenoate; (7Z,10Z,13Z,16Z,19Z)-Docosa 7,10,13,16,19-pentaenoic acid; (7Z,10Z,13Z,16Z,19Z)-Docosa-7,10,13,16,19-pentaenoate; (7Z,10Z,13Z,16Z,19Z)-Docosa-7,10,13,16,19-pentaenoic acid; (all Z)-7,10,13,16,19-Docosapentaenoate; (all Z)-7,10,13,16,19-Docosapentaenoic acid; (all-Z)-7, 10, 13, 16, 19-Docosapentaenoic acid; (all-Z)-7,10,13,16,19-Docosapentaenoic acid; 7,10,13,16,19-Docosapentaenoate; 7,10,13,16,19-Docosapentaenoic acid; 7,10,13,16,19-Docosapentaenoic acid, (all-Z)-isomer; 7Z,10Z,13Z,16Z,19Z-Docosapentaenoate; 7Z,10Z,13Z,16Z,19Z-Docosapentaenoic acid; Clupanodonate; Clupanodonic acid; DPA; DPAn-3; Docosa-7Z,10Z,13Z,16Z,19Z-pentaenoate; Docosa-7Z,10Z,13Z,16Z,19Z-pentaenoic acid; Docosapentaenoate; Docosapentaenoate (22N-3); Docosapentaenoic acid; Docosapentaenoic acid (C22:5 N3); Docosapentaenoic acid, (all Z)-isomer; FA(22:5(7Z,10Z,13Z,16Z,19Z)); FA(22:5n3); Osbond acid; all-cis-7,10,13,16,19-Docosapentaenoate; all-cis-7,10,13,16,19-Docosapentaenoic acid; cis-7,10,13,16,19-Docosapentaenoate; cis-7,10,13,16,19-Docosapentaenoic acid; delta7,10,13,16,19-Docosapentaenoic 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
5497182
HMDB ID
HMDB0006528
Formula
C22H34O2
Structure
<iframe style="width: 300px; height: 300px;" frameborder="0" src="https://embed.molview.org/v1/?mode=balls&cid=5497182"></iframe>
3D MOL 2D MOL
  Click to Show/Hide the Molecular/Functional Data (External Links/Property/Function) of This Metabolite
KEGG ID
C16513
ChEBI ID
53488
FooDB ID
FDB021831
ChemSpider ID
4593750
METLIN ID
194
Physicochemical Properties Molecular Weight 330.5 Topological Polar Surface Area 37.3
XlogP 6.7 Complexity 425
Heavy Atom Count 24 Rotatable Bond Count 15
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 2
Function
Docosapentaenoic acid (22n-3) (also known as clupanodonic acid) is an essential omega-3 fatty acid (EFA) which is prevalent in fish oils. Docosapentaenoic acid, commonly called DPA, is an intermediary between eicosapentaenoic acid (EPA, 20:5 -3) and docosahexaenoic acid (DHA, 22:6 -3). Seal oil is a rich source of this metabolite. There are three functions of docosapentaenoic acid. Most importantly, it is a component of phospholipids found in all animal cell membranes, and a deficiency of docosapentaenoic acid leads to faulty membranes being formed. Secondly, it is involved in the transport and oxidation of cholesterol, and clupanodonic acid tends to lower plasma cholesterol. A third function is as a precursor of prostanoids which are only formed from docosapentaenoic acid. Deficiency of this in experimental animals causes lesions mainly attributable to faulty cellular membranes. Outcomes include sudden failure of growth, lesions of the skin, kidney, and connective tissue, erythrocyte fragility, impaired fertility, and the uncoupling of oxidation and phosphorylation. In humans, pure deficiency of docosapentaenoic acid has been studied particularly in persons fed intravenously. A relative deficiency (that is, a low ratio in the body of docosapentaenoic to long-chain saturated fatty acids and isomers of docosapentaenoate) is common in Western diets and plays an important part in the causation of atherosclerosis, coronary thrombosis, multiple sclerosis, the triopathy of diabetes mellitus, hypertension, and certain forms of malignant disease. Various factors affect the dietary requirement of docosapentaenoic 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 Docosapentaenoic acid (22n-3) concentration: increase (FC = 2.84 / 5.44)
                      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 docosapentaenoic acid (22n-3) 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.

If you find any error in data or bug in web service, please kindly report it to Dr. Zhang and Dr. Mou.