Details of Metabolite

General Information of MET (ID: META00059)
Name Linoleic acid
Synonyms   Click to Show/Hide Synonyms of This Metabolite
(9Z,12Z)-9,12-Octadecadienoate; (9Z,12Z)-9,12-Octadecadienoic acid; (9Z,12Z)-Octadecadienoate; (9Z,12Z)-Octadecadienoic acid; (Z,Z)-9,12-Octadecadienoate; (Z,Z)-9,12-Octadecadienoic acid; 9 trans,12 trans Octadecadienoic acid; 9,12 Octadecadienoic acid; 9,12-Octadecadienoic acid; 9-cis,12-cis-Linoleate; 9-cis,12-cis-Linoleic acid; 9-cis,12-cis-Octadecadienoate; 9-cis,12-cis-Octadecadienoic acid; 9-trans,12-trans-Octadecadienoic acid; 9Z,12Z-Linoleate; 9Z,12Z-Linoleic acid; 9Z,12Z-Octadecadienoate; 9Z,12Z-Octadecadienoic acid; Acid, 9,12-octadecadienoic; Acide cis-linoleique; Acide linoleique; Acido linoleico; C18:2 9C, 12C Omega6 todos cis-9,12-octadienoico; C18:2, N-6,9 all-cis; Emersol 315; Extra linoleic 90; FA(18:2(9Z,12Z)); LA; Linoelaidic acid; Linoelaidic acid, (e,Z)-isomer; Linolate; Linoleate; Linoleic acid, (Z,Z)-isomer; Linoleic acid, (Z,Z)-isomer, 14C-labeled; Linoleic acid, (Z,e)-isomer; Linoleic acid, (e,e)-isomer; Linoleic acid, ammonium salt, (Z,Z)-isomer; Linoleic acid, calcium salt, (Z,Z)-isomer; Linoleic acid, potassium salt, (Z,Z)-isomer; Linoleic acid, sodium salt, (Z,Z)-isomer; Linoleic acid, sodium salt, (e,e)-isomer; Linolelaidic acid; Linolic acid; Polylin 515; Unifac 6550; all-cis-9,12-Octadecadienoate; all-cis-9,12-Octadecadienoic acid; cis,cis-9,12-Octadecadienoate; cis,cis-9,12-Octadecadienoic acid; cis,cis-Linoleate; cis,cis-Linoleic acid; cis-9,cis-12-Octadecadienoate; cis-9,cis-12-Octadecadienoic acid; cis-D9,12-Octadecadienoate; cis-D9,12-Octadecadienoic acid; cis-Delta(9,12)-Octadecadienoic acid; trans,trans-9,12-Octadecadienoic acid
Source Endogenous;Yeast Metabolite;Fatty acyls;Food;Toxins/Pollutant;Cosmetic;Food additives;TCM Ingredients;Microbial
Structure Type   Lineolic acids and derivatives  (Click to Show/Hide the Complete Structure Type Hierarchy)
Lipids and lipid-like molecules
Fatty Acyls
Lineolic acids and derivatives
PubChem CID
5280450
HMDB ID
HMDB0000673
Formula
C18H32O2
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
C01595
ChEBI ID
17351
FooDB ID
FDB006562
ChemSpider ID
4444105
METLIN ID
191
Physicochemical Properties Molecular Weight 280.4 Topological Polar Surface Area 37.3
XlogP 6.8 Complexity 267
Heavy Atom Count 20 Rotatable Bond Count 14
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 2
Function
Linoleic acid is a doubly unsaturated fatty acid, also known as an omega-6 fatty acid, occurring widely in plant glycosides. In this particular polyunsaturated fatty acid (PUFA), the first double bond is located between the sixth and seventh carbon atom from the methyl end of the fatty acid (n-6). Linoleic acid is an essential fatty acid in human nutrition because it cannot be synthesized by humans. It is used in the biosynthesis of prostaglandins (via arachidonic acid) and cell membranes (From Stedman, 26th ed). Linoleic 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
      Nuclear hormone receptor (NHR)
            Factor HNF-4-alpha (HNF4A) 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 Linoleic acid addition (4 hours)
                      Induced Change HNF4A protein activity levels: increase
                      Summary Introduced Variation         Induced Change 
                      Disease Status Type 1 diabetes mellitus [ICD-11: 5A10]
                      Details It is reported that linoleic acid addition causes the increase of HNF4A protein activity compared with control group.
Full List of Protein(s) Regulating This Metabolite
      Hydrolases (EC 3)
            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 [2]
                      Introduced Variation Knockout of Pla2g3
                      Induced Change Linoleic 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 linoleic 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 [3]
                      Introduced Variation Knockout of Scly
                      Induced Change Linoleic 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 linoleic acid levels compared with control group.
      Transferases (EC 2)
            Succinate-hydroxymethylglutarate CoA-transferase (SUGCT) 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 Sugct
                      Induced Change Linoleic acid concentration: increase
                      Summary Introduced Variation         Induced Change 
                      Disease Status Diabetes mellitus [ICD-11: 5A14]
                      Details It is reported that knockout of Sugct leads to the increase of linoleic acid levels compared with control group.
References
1 Identification of an endogenous ligand bound to a native orphan nuclear receptor. PLoS One. 2009;4(5):e5609.
2 Group III phospholipase A 2 promotes colitis and colorectal cancer. Sci Rep. 2017 Sep 25;7(1):12261.
3 Combined Omics Reveals That Disruption of the Selenocysteine Lyase Gene Affects Amino Acid Pathways in Mice. Nutrients. 2019 Oct 26;11(11):2584.
4 Knockout of the non-essential gene SUGCT creates diet-linked, age-related microbiome disbalance with a diabetes-like metabolic syndrome phenotype. Cell Mol Life Sci. 2020 Sep;77(17):3423-3439.

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