Elongation of (very) long chain fatty acids (WP4491)

Mus musculus

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This pathway depicts the key steps in (very) long-chain fatty acid biosynthesis, belonging to the n-10, 9 and 7 series (counting first double bond from the methyl side). These are mainly synthesised from palmitic acid (C16:0), which is produced by FAS (fatty acid synthase). The n-6 and 3 series can only be obtained from precursors in food. The elongation steps (addition of carbohydrates, increasing length of tail) are carried out by several Elovl-proteins. The desaturation (removal of hydrogens, creating double bonds within the tail) are possible by SCDs and Fads (where is position of the double bound addition is indicated after delta, counting from the COOH side).

Authors

Denise Slenter , Egon Willighagen , Conroy lipids , and Alex Pico

Activity

last edited pathway curation

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Cited In

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Organisms

Mus musculus

Communities

Annotations

Pathway Ontology

fatty acid elongation pathway fatty acid metabolic pathway fatty acid biosynthetic pathway

Participants

Label Type Compact URI Comment
C18:2 Metabolite lipidmaps:LMFA01030120 AKA Linoleic Acid
C16:1 Metabolite lipidmaps:LMFA01030267 CCCCCCCCCC=CCCCCC(=O)O C16:1 (omega-10)
AKA Sapienic acid
C18:2 Metabolite lipidmaps:LMFA01030116 CCCCCCC=CCC=CCCCCCCC(=O)O C18:2 (omega-7)(delta6)
8Z,11Z-octadecadienoic acid
C20:2 Metabolite lipidmaps:LMFA01031043 CCCCCC=CCC=CCCCCCCCCCC(=O)O dihomoLinoleic Acid; C20:2 (omega 6)
Excess carbohydrates Metabolite wikidata:Q11358
C18:1 Metabolite lipidmaps:LMFA01030070 CCCCCCCCCC=CCCCCCCC(=O)O C18:1 (omega-10)
cis-8-oleic acid, cis-8-octadecenoic acid
C16:0 Metabolite lipidmaps:LMFA01010001 AKA Palmitic Acid
C18:0 Metabolite lipidmaps:LMFA01010018 AKA Stearic acid
C20:0 Metabolite lipidmaps:LMFA01010020 AKA Arachidic acid
C16:1 Metabolite lipidmaps:LMFA01030056 CCCCCCCCC=CCCCCCC(=O)O C16:1 (omega-9)
AKA Palmitoleic acid
C18:1 Metabolite lipidmaps:LMFA01030076 CCCCCCCCC=CCCCCCCCC(=O)O C18:1 (omega-9)
AKA Vaccenic acid
C16:2 Metabolite lipidmaps:LMFA01030273 CCCCCCC=CCC=CCCCCC(=O)O C16:2 (omega-7)(delta6)
6Z,9Z-hexadecadienoic acid
C20:3 Metabolite lipidmaps:LMFA01030384
C18:2 Metabolite lipidmaps:LMFA01030332 CCCCCCCCC=CCC=CCCCCC(=O)O C18:2 (omega-9)(delta6)
6Z,9Z-octadecadienoic acid
C20:2 Metabolite lipidmaps:LMFA01030377 CCCCCCCCC=CCC=CCCCCCCC(=O)O C20:2 (omega-9)(delta6)
C20:3 Metabolite lipidmaps:LMFA01030381 AKA Mead acid
CCCCCCCCC=CCC=CCC=CCCCCCC(=O)O C20:2 (omega-9)(delta6)(delta5)
C22:3 Metabolite lipidmaps:LMFA01030411 C(CCCCC/C=C\C/C=C\C/C=C\CCCCCCCC)(=O)O
Dihomo Mead's acid
C18:1 Metabolite lipidmaps:LMFA01030002 AKA oleic acid
C20:1 Metabolite lipidmaps:LMFA01030085 cis-gondoic acid
C20:1 (omega-9) aka eicosenoic acid
C22:1 Metabolite lipidmaps:LMFA01030089 AKA Erucic acid
CCCCCCCCC=CCCCCCCCCCCCC(=O)O C22:1 (omega-9)
C24:1 Metabolite lipidmaps:LMFA01030092 CCCCCCCCC=CCCCCCCCCCCCCCC(=O)O C24:1 (omega-9)
Nervonic acid
C22:0 Metabolite lipidmaps:LMFA01010022 AKA Behenic Acid
C24:0 Metabolite lipidmaps:LMFA01010024 AKA Lignoceric acid
C26:0 Metabolite lipidmaps:LMFA01010026 Cerotic acid
C28:0 Metabolite lipidmaps:LMFA01010028 AKA montanic acid (not mentioned in main article).
C30:0 Metabolite lipidmaps:LMFA01010030 AKA melissic acid or triacontanoic acid not mentioned in main article).
C18:3 Metabolite lipidmaps:LMFA01030152 AKA alpha-linolenic acid
C18:3 Metabolite lipidmaps:LMFA01030141 CCCCCC=CCC=CCC=CCCCCC(=O)O gammaLinoleic Acid; C18:3 (omega 6)(delta6)
C18:3 Metabolite lipidmaps:LMFA01030344 Pinolenic acid
C20:3 Metabolite lipidmaps:LMFA01030158 bishomo-gamma-linolenic acid
C20:3 Metabolite lipidmaps:LMFA01030386 Bishomopinolenic acid
C20:4 Metabolite lipidmaps:LMFA01030001 AKA arachidonic acid
C22:4 Metabolite lipidmaps:LMFA01030178 Adrenic acid
C24:4 Metabolite lipidmaps:LMFA01030819 9Z,12Z,15Z,18Z-Tetracosatetraenoic acid
C24:5 Metabolite lipidmaps:LMFA01030820 6Z,9Z,12Z,15Z,18Z-tetracosapentaenoic acid
C22:5 Metabolite lipidmaps:LMFA04000064 AKA Docosapentaenoic acid
C34:5 Metabolite lipidmaps:LMFA01030849 16Z,19Z,22Z,25Z,28Z-tetratriacontapentaenoic acid
C18:4 Metabolite lipidmaps:LMFA01030357 CCC=CCC=CCC=CCC=CCCCCC(=O)O C18:4(omega 3)(delta6)
Stearidonic acid
C20:4 Metabolite lipidmaps:LMFA01030818
C20:5 Metabolite lipidmaps:LMFA01030759 AKA eicosapentaenoic acid
C22:5 Metabolite lipidmaps:LMFA04000044 Clupanodonic acid; DPA
C24:5 Metabolite lipidmaps:LMFA01030821 CCC=CCC=CCC=CCC=CCC=CCCCCCCCC(=O)O C24:5(omega 3)(delta6)(delta5)
C24:6 Metabolite lipidmaps:LMFA01030822 Nisinic acid; THA
C22:6 Metabolite lipidmaps:LMFA01030185 AKA docosahexaenoic acid
C20:3 Metabolite lipidmaps:LMFA01030378 Dihomo-alpha-linolenic acid
C34:6 Metabolite lipidmaps:LMFA01030842
Fas GeneProduct ensembl:ENSMUSG00000025153
Elovl5 GeneProduct ensembl:ENSMUSG00000032349
Elovl3 GeneProduct ensembl:ENSMUSG00000038754
Elovl1 GeneProduct ensembl:ENSMUSG00000006390
Elovl7 GeneProduct ensembl:ENSMUSG00000021696
Elovl6 GeneProduct ensembl:ENSMUSG00000041220
Elovl4 GeneProduct ensembl:ENSMUSG00000032262
Elovl2 GeneProduct ensembl:ENSMUSG00000021364
Fads2 Protein ensembl:ENSMUSG00000024665 Annotated for gene, since:'Fatty acid desaturase 2 (FADS2) is encoded by the FADS2 gene, the associated enzyme is sometimes known as FADS2 as well.[5][6] Its main associated enzyme is Delta 6 desaturase (D6D) however the human enzyme been shown to also catalyze some delta-8 and delta-4 desaturases in spite of naming conventions.'(source: Wikipedia)
Elovl6 Protein ensembl:ENSMUSG00000041220
Elovl5 Protein ensembl:ENSMUSG00000032349
Fads1 Protein ensembl:ENSMUSG00000010663
Elovl3 Protein ensembl:ENSMUSG00000038754
SCD3 Protein uniprot:Q99PL7
SCD1 Protein ensembl:ENSMUSG00000037071
SCD2 Protein uniprot:P13011
SCD4 Protein uniprot:Q6T707
Fads2 ? Protein ensembl:ENSMUSG00000024665 Annotated for gene, since:'Fatty acid desaturase 2 (FADS2) is encoded by the FADS2 gene, the associated enzyme is sometimes known as FADS2 as well.[5][6] Its main associated enzyme is Delta 6 desaturase (D6D) however the human enzyme been shown to also catalyze some delta-8 and delta-4 desaturases in spite of naming conventions.'(source: Wikipedia)
Elovl1 Protein ensembl:ENSMUSG00000006390
Elovl7 Protein ensembl:ENSMUSG00000021696
delta-5 ? Protein ensembl:ENSMUSG00000010663

References

  1. The key roles of elongases and desaturases in mammalian fatty acid metabolism: Insights from transgenic mice. Guillou H, Zadravec D, Martin PGP, Jacobsson A. Prog Lipid Res. 2010 Apr;49(2):186–99. PubMed Europe PMC Scholia
  2. Evidence for an alternative fatty acid desaturation pathway increasing cancer plasticity. Vriens K, Christen S, Parik S, Broekaert D, Yoshinaga K, Talebi A, et al. Nature. 2019 Feb;566(7744):403–6. PubMed Europe PMC Scholia