General Information of MET (ID: META00478)
Name Adrenic acid
Synonyms   Click to Show/Hide Synonyms of This Metabolite
(7Z,10Z,13Z,16Z)-Docosa-7,10,13,16-tetraenoate; (7Z,10Z,13Z,16Z)-Docosa-7,10,13,16-tetraenoic acid; (7Z,10Z,13Z,16Z)-Docosatetraenoate; 7,10,13,16-Docosatetraenoate; 7,10,13,16-Docosatetraenoic acid; 7,10,13,16-Docosatetraenoic acid (van) adrenate; 7,10,13,16-Docosatetraenoic acid (van) adrenic acid; 7Z,10Z,13Z,16Z-Docosatetraenoate; 7Z,10Z,13Z,16Z-Docosatetraenoic acid; Adrenate; Adrenic acid, (Z)-isomer; FA(22:4(7Z,10Z,13Z,16Z)); all-cis-7,10,13,16-Docosatetraenoate; all-cis-7,10,13,16-Docosatetraenoic acid; cis,cis,cis,cis-Docosa-7,10,13,16-tetraensaeure
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
5497181
HMDB ID
HMDB0002226
Formula
C22H36O2
Structure
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3D MOL is unavailable 2D MOL
  Click to Show/Hide the Molecular/Functional Data (External Links/Property/Function) of This Metabolite
KEGG ID
C16527
ChEBI ID
53487
FooDB ID
FDB022918
ChemSpider ID
4593749
METLIN ID
6560
Physicochemical Properties Molecular Weight 332.5 Topological Polar Surface Area 37.3
XlogP 7.4 Complexity 389
Heavy Atom Count 24 Rotatable Bond Count 16
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 2
Function
Adrenic acid, also known as 7,10,13,16-docosatetraenoic acid or adrenate, is a member of the class of compounds known as very long-chain fatty acids. Very long-chain fatty acids are fatty acids with an aliphatic tail that contains at least 22 carbon atoms. Adrenic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Adrenic acid can be found in blood and in human myelin tissue. Within the cell, adrenic acid is primarily located in the cytoplasm, in the membrane (predicted from logP), and in the peroxisome. It can also be found in the extracellular space. In humans, adrenic acid is involved in alpha-linolenic acid and linoleic acid metabolism. Docosatetraenoic acid designates any straight chain 22:4 fatty acid. In particular, all-cis-7,10,13,16-docosatetraenoic acid is an -6 fatty acid with the trivial name adrenic acid (AdA). This is a naturally occurring polyunsaturated fatty acid formed through a 2-carbon chain elongation of arachidonic acid. It is one of the most abundant fatty acids in the early human brain. This unsaturated fatty acid is also metabolized by cells into biologically active products, such as dihomoprostaglandins and dihomo-epoxyeicosatrienoic acids (dihomo-EETs). Adrenic acid, which is a prostacyclin inhibitor, appears to be a potential prothrombotic agent.
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 Adrenic acid concentration: increase (FC = 3.02)
                      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 adrenic 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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