General Information of MET (ID: META01249)
Name Arachidonic acid
Synonyms   Click to Show/Hide Synonyms of This Metabolite
arachidonate; (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoate; 506-32-1; CHEBI:32395; C20:4 fatty acid; (5Z,8Z,11Z,14Z)-icosatetraenoate; (5Z,8Z,11Z,14Z)-eicosatetraenoate; all-cis-icosa-5,8,11,14-tetraenoate; (20:4n6); A828211; (5Z,8Z,11Z,14Z)-eicosa-5,8,11,14-tetraenoate; (5Z,8Z,11Z,14Z)-icosatetra-5,8,11,14-enoate; Q27104215
Source Aliphatic acyclic compounds
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
C20H31O2-
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 303.5 Topological Polar Surface Area 40.1
XlogP 6.9 Complexity 356
Heavy Atom Count 22 Rotatable Bond Count 13
Hydrogen Bond Donor Count N.A. 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
      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 Arachidonic acid concentration: increase
                      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 arachidonic 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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