Details of Metabolite

General Information of MET (ID: META00036)
Name Docosahexaenoic acid
Synonyms   Click to Show/Hide Synonyms of This Metabolite
(4Z,7Z,10Z,13Z,16Z,19Z)-4,7,10,13,16,19-Docosahexaenoic acid; (4Z,7Z,10Z,13Z,16Z,19Z)-Docosa-4,7,10,13,16,19-hexaenoate; (4Z,7Z,10Z,13Z,16Z,19Z)-Docosa-4,7,10,13,16,19-hexaenoic acid; (4Z,7Z,10Z,13Z,16Z,19Z)-Docosahexaenoate; (4Z,7Z,10Z,13Z,16Z,19Z)-Docosahexaenoic acid; (4Z,7Z,10Z,13Z,16Z,19Z)-Docosahexenoic acid; (all-Z)-4,7,10,13,16,19-Docosahexaenoic acid; 22:6(N-3); 22:6-4, 7,10,13,16,19; 4,7,10,13,16,19-Docosahexaenoate; 4,7,10,13,16,19-Docosahexaenoic acid; 4-cis,7-cis,10-cis,13-cis,16-cis,19-cis-Docosahexaenoic acid; 4Z,7Z,10Z,13Z,16Z,19Z-Docosahexaenoate; 4Z,7Z,10Z,13Z,16Z,19Z-Docosahexaenoic acid; Acids, docosahexaenoic; Acids, docosahexenoic; Cervonate; Cervonic acid; DHA; DOCOSA-4,7,10,13,16,19-hexaenoIC ACID; DOCOSA-4,7,10,13,16,19-hexaenoate; Doconexent; Doconexento; Doconexentum; Docosahexaenoate; Docosahexaenoic acid; Docosahexaenoic acid (all-Z isomer); Docosahexaenoic acid, 4,7,10,13,16,19-(all-Z-isomer); Docosahexaenoic acid, 4,7,10,13,16,19-isomer; Doxonexent; Efalex; FA(22:6(4Z,7Z,10Z,13Z,16Z,19Z)); FA(22:6n3); all-Z-Docosahexaenoate; all-Z-Docosahexaenoic acid; all-cis-4,7,10,13,16,19-Docosahexaenoate; all-cis-4,7,10,13,16,19-Docosahexaenoic acid; all-cis-DHA; cis-4,7,10,13,16,19-Docosahexanoate; cis-4,7,10,13,16,19-Docosahexanoic 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
445580
HMDB ID
HMDB0002183
Formula
C22H32O2
Structure
<iframe style="width: 300px; height: 300px;" frameborder="0" src="https://embed.molview.org/v1/?mode=balls&cid=445580"></iframe>
3D MOL 2D MOL
  Click to Show/Hide the Molecular/Functional Data (External Links/Property/Function) of This Metabolite
KEGG ID
C06429
DrugBank ID
DB03756
ChEBI ID
28125
FooDB ID
FDB003003
ChemSpider ID
393183
METLIN ID
3457
Physicochemical Properties Molecular Weight 328.5 Topological Polar Surface Area 37.3
XlogP 6.2 Complexity 462
Heavy Atom Count 24 Rotatable Bond Count 14
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 2
Function
Docosahexaenoic acid (DHA) is an omega-3 essential fatty acid. Chemically, DHA is a carboxylic acid with a 22-carbon chain and six cis- double bonds with the first double bond located at the third carbon from the omega end. DHA is most often found in fish oil. It is a major fatty acid in sperm and brain phospholipids, especially in the retina. Dietary DHA can reduce the level of blood triglycerides in humans, which may reduce the risk of heart disease. Docosahexaenoic acid is found to be associated with isovaleric acidemia, which is an inborn error of metabolism.
Regulatory Network
Full List of Protein(s) Regulated by This Metabolite
      Gastrin/cholecystokinin (GCK)
            Cholecystokinin (CCK) 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 Docosahexaenoic acid addition (0.33 hours)
                      Induced Change CCK protein expression levels: increase
                      Summary Introduced Variation         Induced Change 
                      Disease Status Healthy individual
                      Details It is reported that docosahexaenoic acid addition causes the increase of CCK protein expression compared with control group.
Full List of Protein(s) Regulating This Metabolite
      GPH:cation symporter (GCS)
            Sodium-dependent lysophosphatidylcholine symporter 1 (MFSD2A) 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 MFSD2A
                      Induced Change Docosahexaenoic acid concentration: decrease
                      Summary Introduced Variation         Induced Change 
                      Disease Status Healthy individual
                      Details It is reported that knockout of MFSD2A leads to the decrease of docosahexaenoic acid levels compared with control group.
      Hydrolases (EC 3)
            Group 10 secretory phospholipase A2 (PLA2G10) Click to Show/Hide the Full List of Regulating Pair(s):   2 Pair(s)
               Detailed Information Protein   Info click to show the details of this protein
               Regulating Pair (1) Experim Info click to show the details of experiment for validating this pair [3]
                      Introduced Variation Overexpression of Pla2g10
                      Induced Change Docosahexaenoic acid concentration: increase
                      Summary Introduced Variation         Induced Change 
                      Disease Status Inflammatory bowel disease [ICD-11: DD72]
                      Details It is reported that overexpression of Pla2g10 leads to the increase of docosahexaenoic acid levels compared with control group.
               Regulating Pair (2) Experim Info click to show the details of experiment for validating this pair [3]
                      Introduced Variation Knockout of Pla2g10
                      Induced Change Docosahexaenoic acid concentration: decrease
                      Summary Introduced Variation         Induced Change 
                      Disease Status Inflammatory bowel disease [ICD-11: DD72]
                      Details It is reported that knockout of Pla2g10 leads to the decrease of docosahexaenoic acid levels compared with control group.
            Group 3 secretory phospholipase A2 (PLA2G3) 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 [4]
                      Introduced Variation Knockout of Pla2g3
                      Induced Change Docosahexaenoic acid concentration: increase
                      Summary Introduced Variation         Induced Change 
                      Disease Status Colorectal cancer [ICD-11: 2B91]
                      Details It is reported that knockout of Pla2g3 leads to the increase of docosahexaenoic acid levels compared with control group.
References
1 TRPA1 is a polyunsaturated fatty acid sensor in mammals. PLoS One. 2012;7(6):e38439.
2 Mfsd2a is a transporter for the essential omega-3 fatty acid docosahexaenoic acid. Nature. 2014 May 22;509(7501):503-6.
3 Group X Secreted Phospholipase A2 Releases 3 Polyunsaturated Fatty Acids, Suppresses Colitis, and Promotes Sperm Fertility. J Biol Chem. 2016 Mar 25;291(13):6895-911.
4 Group III phospholipase A 2 promotes colitis and colorectal cancer. Sci Rep. 2017 Sep 25;7(1):12261.

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