General Information of MET (ID: META00361)
Name Arachidonic acid
Synonyms   Click to Show/Hide Synonyms of This Metabolite
(5Z,8Z,11Z,14Z)-5,8,11,14-Icosatetraenoate; (5Z,8Z,11Z,14Z)-5,8,11,14-Icosatetraenoic acid; (5Z,8Z,11Z,14Z)-Icosa-5,8,11,14-tetraenoate; (5Z,8Z,11Z,14Z)-Icosa-5,8,11,14-tetraenoic acid; (5Z,8Z,11Z,14Z)-Icosatetraenoate; (5Z,8Z,11Z,14Z)-Icosatetraenoic acid; (all-Z)-5,8,11,14-Eicosatetraenoate; (all-Z)-5,8,11,14-Eicosatetraenoic acid; 5,8,11,14-Eicosatetraenoate; 5,8,11,14-Eicosatetraenoic acid; 5,8,11,14-all-cis-Eicosatetraenoate; 5,8,11,14-all-cis-Eicosatetraenoic acid; 5-cis,8-cis,11-cis,14-cis-Eicosatetraenoate; 5-cis,8-cis,11-cis,14-cis-Eicosatetraenoic acid; 5Z,8Z,11Z,14Z-Eicosatetraenoate; 5Z,8Z,11Z,14Z-Eicosatetraenoic acid; AA; ARA; Arachidonate; Arachidonate, sodium; Arachidonic acid, (all-Z)-isomer, 1-(14)C-labeled; Arachidonic acid, (all-Z)-isomer, 3H-labeled; Arachidonic acid, ammonium salt, (all-Z)-isomer; Arachidonic acid, cerium salt, (all-Z)-isomer; Arachidonic acid, cesium salt, (all-Z)-isomer; Arachidonic acid, lithium salt, (all-Z)-isomer; Arachidonic acid, potassium salt, (all-Z)-isomer; Arachidonic acid, sodium salt; Arachidonic acid, sodium salt, (all-Z)-isomer; Arachidonic acid, zinc salt, (all-Z)-isomer; Arachidonsaeure; FA(20:4(5Z,8Z,11Z,14Z)); FA(20:4n6); Immunocytophyte; Sodium arachidonate; Vitamin F; all-cis-5,8,11,14-Eicosatetraenoate; all-cis-5,8,11,14-Eicosatetraenoic acid; cis-5,8,11,14-Eicosatetraenoate; cis-5,8,11,14-Eicosatetraenoic acid; cis-D5,8,11,14-Eicosatetraenoate; cis-D5,8,11,14-Eicosatetraenoic acid; cis-Delta(5,8,11,14)-Eicosatetraenoic acid
Source Endogenous;Fatty acyls;Food;TCM Ingredients
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
444899
HMDB ID
HMDB0001043
Formula
C20H32O2
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
C00219
DrugBank ID
DB04557
ChEBI ID
15843
FooDB ID
FDB011872
ChemSpider ID
392692
METLIN ID
193
Physicochemical Properties Molecular Weight 304.5 Topological Polar Surface Area 37.3
XlogP 6.3 Complexity 362
Heavy Atom Count 22 Rotatable Bond Count 14
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 2
Function
Arachidonic acid is a polyunsaturated, essential fatty acid that has a 20-carbon chain as a backbone and four cis-double bonds at the C5, C8, C11, and C14 positions. It is found in animal and human fat as well as in the liver, brain, and glandular organs, and is a constituent of animal phosphatides. It is synthesized from dietary linoleic acid. Arachidonic acid mediates inflammation and the functioning of several organs and systems either directly or upon its conversion into eicosanoids. Arachidonic acid in cell membrane phospholipids is the substrate for the synthesis of a range of biologically active compounds (eicosanoids) including prostaglandins, thromboxanes, and leukotrienes. These compounds can act as mediators in their own right and can also act as regulators of other processes, such as platelet aggregation, blood clotting, smooth muscle contraction, leukocyte chemotaxis, inflammatory cytokine production, and immune function. Arachidonic acid can be metabolized by cytochrome p450 (CYP450) enzymes into 5,6-, 8,9-, 11,12-, and 14,15-epoxyeicosatrienoic acids (EETs), their corresponding dihydroxyeicosatrienoic acids (DHETs), and 20-hydroxyeicosatetraenoic acid (20-HETE). The production of kidney CYP450 arachidonic acid metabolites is altered in diabetes, pregnancy, hepatorenal syndrome, and in various models of hypertension, and it is likely that changes in this system contribute to the abnormalities in renal function that are associated with many of these conditions. Phospholipase A2 (PLA2) catalyzes the hydrolysis of the sn-2 position of membrane glycerophospholipids to liberate arachidonic acid. The beneficial effects of omega-3 fatty acids are believed to be due in part to selective alteration of arachidonate metabolism that involves cyclooxygenase (COX) enzymes. 9-Oxononanoic acid (9-ONA), one of the major products of peroxidized fatty acids, was found to stimulate the activity of phospholipase A2 (PLA2), the key enzyme to initiate the arachidonate cascade and eicosanoid production. Arachidonate lipoxygenase (ALOX) enzymes metabolize arachidonic acid to generate potent inflammatory mediators and play an important role in inflammation-associated diseases.
Regulatory Network
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 [1]
                      Introduced Variation Knockout of MFSD2A
                      Induced Change Arachidonic acid concentration: increase (FC = 1.34)
                      Summary Introduced Variation         Induced Change 
                      Disease Status Healthy individual
                      Details It is reported that knockout of MFSD2A leads to the increase of arachidonic 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 [2]
                      Introduced Variation Knockout of Pla2g10
                      Induced Change Arachidonic 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 arachidonic acid levels compared with control group.
               Regulating Pair (2) Experim Info click to show the details of experiment for validating this pair [2]
                      Introduced Variation Overexpression of Pla2g10
                      Induced Change Arachidonic 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 arachidonic 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 [3]
                      Introduced Variation Knockout of Pla2g3
                      Induced Change Arachidonic 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 arachidonic acid levels compared with control group.
      Lyases (EC 4)
            Selenocysteine lyase (SCLY) 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 Scly
                      Induced Change Arachidonic acid concentration: decrease
                      Summary Introduced Variation         Induced Change 
                      Disease Status Healthy individual
                      Details It is reported that knockout of Scly leads to the decrease of arachidonic acid levels compared with control group.
References
1 Mfsd2a is a transporter for the essential omega-3 fatty acid docosahexaenoic acid. Nature. 2014 May 22;509(7501):503-6.
2 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.
3 Group III phospholipase A 2 promotes colitis and colorectal cancer. Sci Rep. 2017 Sep 25;7(1):12261.
4 Combined Omics Reveals That Disruption of the Selenocysteine Lyase Gene Affects Amino Acid Pathways in Mice. Nutrients. 2019 Oct 26;11(11):2584.

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