Details of Metabolite (Meta)

General Information of Metabolite (ID: MT041)
  Meta Name
Linoleic acid derivative
  Unify Name
Linoleic acid
  Synonym    Click to Show/Hide the Detailed Synonyms of This Metabolite
(9Z,12Z)-Octadecadienoic acid;(Z,Z)-9,12-Octadecadienoic acid;9-cis,12-cis-Octadecadienoic acid;9Z,12Z-Octadecadienoic acid;Acide cis-linoleique;Acide linoleique;Acido linoleico;all-cis-9,12-Octadecadienoic acid;C18:2 9C, 12C Omega6 todos cis-9,12-octadienoico;C18:2, N-6,9 all-cis;cis,cis-9,12-Octadecadienoic acid;cis,cis-Linoleic acid;cis-Delta(9,12)-Octadecadienoic acid;LA;Linolic acid;9-cis,12-cis-Octadecadienoate;(9Z,12Z)-Octadecadienoate;(Z,Z)-9,12-Octadecadienoate;9Z,12Z-Octadecadienoate;all-cis-9,12-Octadecadienoate;cis,cis-9,12-Octadecadienoate;cis,cis-Linoleate;cis-delta(9,12)-Octadecadienoate;cis-delta(9,12)-octadecadienoate;cis-delta(9,12)-octadecadienoic acid;Linolate;Linoleate;(9Z,12Z)-9,12-Octadecadienoate;(9Z,12Z)-9,12-Octadecadienoic acid;9-cis,12-cis-Linoleate;9-cis,12-cis-Linoleic acid;9Z,12Z-Linoleate;9Z,12Z-Linoleic acid;cis-9,cis-12-Octadecadienoate;cis-9,cis-12-Octadecadienoic acid;cis-D9,12-Octadecadienoate;cis-D9,12-Octadecadienoic acid;Emersol 315;Extra linoleic 90;Polylin 515;Unifac 6550;Acid, 9,12-octadecadienoic;Linoelaidic acid;Linoleic acid, (e,e)-isomer;Linoleic acid, (Z,Z)-isomer;Linoleic acid, (Z,Z)-isomer, 14C-labeled;Linoleic acid, ammonium salt, (Z,Z)-isomer;Linoleic acid, potassium salt, (Z,Z)-isomer;9 trans,12 trans Octadecadienoic acid;9-trans,12-trans-Octadecadienoic acid;Linoleic acid, sodium salt, (e,e)-isomer;Linoleic acid, sodium salt, (Z,Z)-isomer;trans,trans-9,12-Octadecadienoic acid;9,12-Octadecadienoic acid;Linoelaidic acid, (e,Z)-isomer;Linoleic acid, calcium salt, (Z,Z)-isomer;Linolelaidic acid;9,12 Octadecadienoic acid;Linoleic acid, (Z,e)-isomer;FA(18:2(9Z,12Z))
  Molecule Type
Polyunsaturated fatty acid (PUFAs)
  Formula
C18H31O2
  Inchi Key
OYHQOLUKZRVURQ-HZJYTTRNSA-M
  Description    Click to Show/Hide the Detailed Description of This Metabolite
Human Metabolome Database (HMDB): 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.
  External Links   HMDB ID   HMDB0000673
  VMH ID   lnlc
  KEGG ID   C01595
  Metlin ID   191

The epigenetic modification information of this metabolite
Modification Type Molecule EM Info Cell/Tissue Type Modified sites Condition REF
DNA Methylation DNMT EM Info . . . [1], [2]
Histone Deacetylation SIRT1 EM Info . . . [1], [2]

The microbes that produce this metabolite
      Roseburia
         Detailed Information MIC Info click to show the detail information of this Microbiota [3], [1]
         Description
Roseburia is a genus of butyrate-producing, gram-positive anaerobic bacteria that inhabit the human colon.
      Klebsiella
         Detailed Information MIC Info click to show the detail information of this Microbiota [1], [2]
         Description
Klebsiella is a genus of gram-negative, oxidase-negative, rod-shaped bacteria from the family Enterobacteriaceae
      Enterobacter
         Detailed Information MIC Info click to show the detail information of this Microbiota [1], [2]
         Description
Enterobacter is a genus of common gram-negative, facultatively anaerobic, rod-shaped, non-spore-forming bacteria of the family Enterobacteriaceae. It is the type genus of the order Enterobacterales.
      Citrobacter
         Detailed Information MIC Info click to show the detail information of this Microbiota [1], [2]
         Description
Citrobacter is a genus of gram-negative coliform bacteria in the family Enterobacteriaceae. The species C. amalonaticus, C. koseri, and C. freundii can use citrate as a sole carbon source. Citrobacter species are differentiated by their ability to convert tryptophan to indole, ferment lactose, and use malonate.

References
1 Gut Microbiota as Important Mediator Between Diet and DNA Methylation and Histone Modifications in the Host. Nutrients. 2020 Feb 25;12(3):597. doi: 10.3390/nu12030597.
2 Arachidonic and oleic acid exert distinct effects on the DNA methylome. Epigenetics. 2016 May 3;11(5):321-34. doi: 10.1080/15592294.2016.1161873. Epub 2016 Apr 18.
3 Valerian and valeric acid inhibit growth of breast cancer cells possibly by mediating epigenetic modifications. Sci Rep. 2021 Jan 28;11(1):2519. doi: 10.1038/s41598-021-81620-x.

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