Elongation of (very) long chain fatty acids (Mus musculus)

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21Delta-8Double bondDelta-6Double bondomega 10 (or n-10) family(delta7,11,14)DIETDelta-5Double bondFads2C18:2Elovl6C20:2C18:2Excess carbohydratesFasC16:1C18:1C16:0C18:0C20:0C16:1C18:1C16:2C18:3C20:3C18:2C20:2C20:3C22:3C18:1C20:1C22:1C24:1omega 9 (or n-9) familyomega 6 (or n-6) familyC22:0C24:0C26:0C28:0C30:0Saturated fatty acidsElovl5Elovl5Fads1Elovl3Elovl3Elovl3SCD3SCD1SCD2SCD4Fads2 ?Fads2SCD2SCD4SCD1Elovl3Elovl1Elovl7Elovl6Elovl3Elovl1Elovl7Elovl3Elovl1Elovl7Elovl3Elovl1Elovl4C18:3C18:3C18:3C20:3C20:3C20:4C22:4C24:4C24:5C22:5C34:5C18:4C20:4C20:5C22:5C24:5C24:6C22:6C20:3C34:6Elovl5Fads2delta-5 ? Elovl5?Fads1Elovl5Elovl2Elovl2Fads2Elovl4Elovl2Perox. beta-oxElovl4Elovl2Fads2Elovl5Elovl5Fads2omega 7 (or n-7) familyomega 3 (or n-3) familyDelta-9Double bondDelta-9Double bondDelta-6Double bondDelta-6Double bondDelta-6Double bondDelta-5Double bondDelta-6Double bondDelta-6Double bond????Elovl6Elovl511


Description

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).

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Quality Tags

Ontology Terms

 

Bibliography

  1. Vriens K, Christen S, Parik S, Broekaert D, Yoshinaga K, Talebi A, Dehairs J, Escalona-Noguero C, Schmieder R, Cornfield T, Charlton C, Romero-Pérez L, Rossi M, Rinaldi G, Orth MF, Boon R, Kerstens A, Kwan SY, Faubert B, Méndez-Lucas A, Kopitz CC, Chen T, Fernandez-Garcia J, Duarte JAG, Schmitz AA, Steigemann P, Najimi M, Hägebarth A, Van Ginderachter JA, Sokal E, Gotoh N, Wong KK, Verfaillie C, Derua R, Munck S, Yuneva M, Beretta L, DeBerardinis RJ, Swinnen JV, Hodson L, Cassiman D, Verslype C, Christian S, Grünewald S, Grünewald TGP, Fendt SM; ''Evidence for an alternative fatty acid desaturation pathway increasing cancer plasticity.''; Nature, 2019 PubMed Europe PMC Scholia
  2. Guillou H, Zadravec D, Martin PG, Jacobsson A; ''The key roles of elongases and desaturases in mammalian fatty acid metabolism: Insights from transgenic mice.''; Prog Lipid Res, 2010 PubMed Europe PMC Scholia

History

View all...
CompareRevisionActionTimeUserComment
125976view15:58, 23 March 2023DeSlAdded info on uncertainty of existance for C18:3
125917view02:26, 18 March 2023AlexanderPicomanual sync
125884view14:37, 16 March 2023Conroy lipidsfix more cross refs
125883view14:14, 16 March 2023Conroy lipidscorrected more erroneous identifiers for lipids
125882view13:47, 16 March 2023Conroy lipidsmetabolite IDs changed for lipidmaps IDs and updated for correct metabolites (previous ones had incorrect double bond position and geometry)
125771view15:12, 9 March 2023DeSlAdded last missing metabolite
125770view15:10, 9 March 2023DeSlAnnotated bottom section
125769view15:06, 9 March 2023DeSlAnnotated purple section
125768view14:58, 9 March 2023DeSlFinished annotating top half
125767view14:56, 9 March 2023DeSlAnnotated top 2 sections based on SMILES
107306view14:40, 19 September 2019EgonwRemoved an empty ChEBI identifier
107208view14:30, 17 September 2019MaintBotChEBI identifier normalization
103499view14:31, 6 March 2019DeSlAdded proteins for C16:1 -> C18:1 omega 10 conversion.
102579view13:42, 9 January 2019DeSlAdded excess carbohydrates Node as substrate for C16:0
102578view13:37, 9 January 2019DeSlAdded SMILES for Omega-3 series.
102577view13:23, 9 January 2019DeSlAdded SMILES in comments for Omega 6 series.
102576view13:07, 9 January 2019DeSlAnnotated saturated fatty acid serie.
102575view12:56, 9 January 2019DeSlAdded SMILES in comments for omega 9 and 7 family.
102574view12:43, 9 January 2019DeSlAnnotated missing Elovl5+6
102573view12:40, 9 January 2019DeSlAdded delta information as text lables (iso in the protein nodes).
102571view13:27, 8 January 2019DeSlModified description
102570view13:25, 8 January 2019DeSlAnnotated SCD3
102569view13:23, 8 January 2019DeSlAnnotated SCD series (except nr3)
102568view13:19, 8 January 2019DeSlAdded "aka name" in comment for C(18:1)n-10
102567view13:07, 8 January 2019DeSlAnnotated more lipids (with names from Fig.1 of main publication).
102558view16:00, 7 January 2019DeSlOntology Term : 'fatty acid metabolic pathway' added !
102557view16:00, 7 January 2019DeSlOntology Term : 'fatty acid biosynthetic pathway' added !
102556view15:59, 7 January 2019DeSlOntology Term : 'fatty acid elongation pathway' added !
102555view15:57, 7 January 2019DeSlModified description
102554view15:52, 7 January 2019DeSlLayout changes
102551view15:50, 7 January 2019DeSlAdded background for omage 6 and 3 compounds
102550view15:15, 7 January 2019DeSlAdded proteins for bottom half
102549view15:00, 7 January 2019DeSlAdded bottom half of figure
102548view14:49, 7 January 2019DeSlAdded SMILES for some lipids in the comment section (will annotate later with specific ID).
102547view13:50, 7 January 2019DeSlModified description
102546view13:47, 7 January 2019DeSlAnnotated more proteins
102545view13:22, 7 January 2019DeSlAnnotated Elovl proteins
102544view13:17, 7 January 2019DeSlNew pathway

External references

DataNodes

View all...
NameTypeDatabase referenceComment
C16:0MetaboliteLMFA01010001 (LIPID MAPS) AKA Palmitic Acid
C16:1MetaboliteLMFA01030056 (LIPID MAPS)
  • CCCCCCCCC=CCCCCCC(=O)O C16:1 (omega-9)
  • AKA Palmitoleic acid
C16:1MetaboliteLMFA01030267 (LIPID MAPS)
  • CCCCCCCCCC=CCCCCC(=O)O C16:1 (omega-10)
  • AKA Sapienic acid
C16:2MetaboliteLMFA01030273 (LIPID MAPS)
  • CCCCCCC=CCC=CCCCCC(=O)O C16:2 (omega-7)(delta6)
  • 6Z,9Z-hexadecadienoic acid
C18:0MetaboliteLMFA01010018 (LIPID MAPS) AKA Stearic acid
C18:1MetaboliteLMFA01030002 (LIPID MAPS) AKA oleic acid
C18:1MetaboliteLMFA01030070 (LIPID MAPS)
  • CCCCCCCCCC=CCCCCCCC(=O)O C18:1 (omega-10)
  • cis-8-oleic acid, cis-8-octadecenoic acid
C18:1MetaboliteLMFA01030076 (LIPID MAPS)
  • CCCCCCCCC=CCCCCCCCC(=O)O C18:1 (omega-9)
  • AKA Vaccenic acid
C18:2MetaboliteLMFA01030116 (LIPID MAPS)
  • CCCCCCC=CCC=CCCCCCCC(=O)O C18:2 (omega-7)(delta6)
  • 8Z,11Z-octadecadienoic acid
C18:2MetaboliteLMFA01030120 (LIPID MAPS) AKA Linoleic Acid
C18:2MetaboliteLMFA01030332 (LIPID MAPS)
  • CCCCCCCCC=CCC=CCCCCC(=O)O C18:2 (omega-9)(delta6)
  • 6Z,9Z-octadecadienoic acid
C18:3Metabolite
C18:3MetaboliteLMFA01030141 (LIPID MAPS) CCCCCC=CCC=CCC=CCCCCC(=O)O gammaLinoleic Acid; C18:3 (omega 6)(delta6)
C18:3MetaboliteLMFA01030344 (LIPID MAPS) Pinolenic acid
C18:3MetaboliteQ256502 (Wikidata) AKA alpha-linolenic acid
C18:4MetaboliteJIWBIWFOSCKQMA-GFRMADBLSA-N (InChIKey) CCC=CCC=CCC=CCC=CCCCCC(=O)O C18:4(omega 3)(delta6)
C20:0MetaboliteLMFA01010020 (LIPID MAPS) AKA Arachidic acid
C20:1MetaboliteLMFA01030085 (LIPID MAPS)
  • cis-gondoic acid
  • C20:1 (omega-9) aka eicosenoic acid
C20:2MetaboliteLMFA01030377 (LIPID MAPS) CCCCCCCCC=CCC=CCCCCCCC(=O)O C20:2 (omega-9)(delta6)
C20:2MetaboliteLMFA01031043 (LIPID MAPS) CCCCCC=CCC=CCCCCCCCCCC(=O)O dihomoLinoleic Acid; C20:2 (omega 6)
C20:3MetaboliteAHANXAKGNAKFSK-IUQGRGSQSA-N (InChIKey) CCC=CCC=CCC=CCCCCCCCCCC(=O)O C20:3(omega 3)
C20:3MetaboliteLMFA01030158 (LIPID MAPS) bishomo-gamma-linolenic acid
C20:3MetaboliteLMFA01030381 (LIPID MAPS)
  • AKA Mead acid
  • CCCCCCCCC=CCC=CCC=CCCCCCC(=O)O C20:2 (omega-9)(delta6)(delta5)
C20:3MetaboliteLMFA01030384 (LIPID MAPS)
C20:3MetaboliteLMFA01030386 (LIPID MAPS) Bishomopinolenic acid
C20:4Metabolite
  • CCC=CCC=CCC=CCC=CCCCCCCC(=O)O C20:4(omega 3)(delta6)
  • Following other route: CCC=CCC=CCC=CCC=CCCCCCCC(=O)O C20:4(omega 3)(delta8)
C20:4MetaboliteLMFA01030001 (LIPID MAPS)
  • AKA arachidonic acid
C20:5MetaboliteQ409990 (Wikidata)
  • AKA eicosapentaenoic acid
  • CCC=CCC=CCC=CCC=CCC=CCCCC(=O)O C20:5(omega 3)(delta6)(delta5)
C22:0MetaboliteLMFA01010022 (LIPID MAPS) AKA Behenic Acid
C22:1MetaboliteLMFA01030089 (LIPID MAPS)
  • AKA Erucic acid
  • CCCCCCCCC=CCCCCCCCCCCCC(=O)O C22:1 (omega-9)
C22:3MetaboliteLMFA01030411 (LIPID MAPS)
  • C(CCCCC/C=C\C/C=C\C/C=C\CCCCCCCC)(=O)O
  • Dihomo Mead's acid
C22:4MetaboliteLMFA01030178 (LIPID MAPS) Adrenic acid
C22:5MetaboliteLMFA04000064 (LIPID MAPS)
  • AKA Docosapentaenoic acid
C22:5MetaboliteYUFFSWGQGVEMMI-RCHUDCCISA-N (InChIKey) CCC=CCC=CCC=CCC=CCC=CCCCCCC(=O)O C22:5(omega 3)(delta6)(delta5)
C22:6MetaboliteQ423345 (Wikidata)
  • AKA docosahexaenoic acid (currently annotated with all-cis version of lipid, however there is an all trans version: Q27094656)
  • CCC=CCC=CCC=CCC=CCC=CCC=CCCC(=O)O C22:6(omega 3)(delta6)(delta5)(delta6)
C24:0MetaboliteLMFA01010024 (LIPID MAPS) AKA Lignoceric acid
C24:1MetaboliteLMFA01030092 (LIPID MAPS)
  • CCCCCCCCC=CCCCCCCCCCCCCCC(=O)O C24:1 (omega-9)
  • Nervonic acid
C24:4MetaboliteLMFA01030819 (LIPID MAPS) 9Z,12Z,15Z,18Z-Tetracosatetraenoic acid
C24:5MetaboliteLMFA01030820 (LIPID MAPS) 6Z,9Z,12Z,15Z,18Z-tetracosapentaenoic acid
C24:5MetaboliteNPTIBOCVSPURCS-RCHUDCCISA-N (InChIKey) CCC=CCC=CCC=CCC=CCC=CCCCCCCCC(=O)O C24:5(omega 3)(delta6)(delta5)
C24:6MetaboliteYHGJECVSSKXFCJ-SFGLVEFQSA-N (InChIKey) CCC=CCC=CCC=CCC=CCC=CCC=CCCCCC(=O)O C24:6(omega 3)(delta6)(delta5)(delta6)
C26:0MetaboliteLMFA01010026 (LIPID MAPS) Cerotic acid
C28:0MetaboliteLMFA01010028 (LIPID MAPS) AKA montanic acid (not mentioned in main article).
C30:0MetaboliteLMFA01010030 (LIPID MAPS) AKA melissic acid or triacontanoic acid not mentioned in main article).
C34:5MetaboliteLMFA01030849 (LIPID MAPS) 16Z,19Z,22Z,25Z,28Z-tetratriacontapentaenoic acid
C34:6MetaboliteTZKUXMFOWSEBLN-SFGLVEFQSA-N (InChIKey) CCC=CCC=CCC=CCC=CCC=CCC=CCCCCCCCCCCCCCCC(=O)O C34:6(omega 3)(delta6)(delta5)(delta6)
Elovl1ProteinENSMUSG00000006390 (Ensembl)
Elovl2GeneProductENSMUSG00000021364 (Ensembl)
Elovl3ProteinENSMUSG00000038754 (Ensembl)
Elovl4GeneProductENSMUSG00000032262 (Ensembl)
Elovl5ProteinENSMUSG00000032349 (Ensembl)
Elovl6ProteinENSMUSG00000041220 (Ensembl)
Elovl7ProteinENSMUSG00000021696 (Ensembl)
Excess carbohydratesMetaboliteQ11358 (Wikidata)
Fads1ProteinENSMUSG00000010663 (Ensembl)
Fads2 ?ProteinENSMUSG00000024665 (Ensembl) 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)
Fads2ProteinENSMUSG00000024665 (Ensembl) 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)
FasGeneProductENSMUSG00000025153 (Ensembl)
Perox. beta-oxProtein
SCD1ProteinENSMUSG00000037071 (Ensembl)
SCD2ProteinP13011 (Uniprot-TrEMBL)
SCD3ProteinQ99PL7 (Uniprot-TrEMBL)
SCD4ProteinQ6T707 (Uniprot-TrEMBL)
delta-5 ? ProteinENSMUSG00000010663 (Ensembl)

Annotated Interactions

No annotated interactions

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