Octadecanoid formation from linoleic acid (WP5324)

Homo sapiens

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The main enzymatic processes involved in the formation of 18-carbon fatty acids from linoleic acid.

Authors

Conroy lipids and Alex Pico

Activity

last edited

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Cited In

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Organisms

Homo sapiens

Communities

Lipids and LIPID MAPS

Annotations

Pathway Ontology

lipid metabolic pathway lipid signaling pathway linoleic acid metabolic pathway

Participants
Query Drugst.One

Label Type Compact URI Comment
9(R)-HODE Metabolite lipidmaps:LMFA02000036
9,10-epoxy-13-hydroxy-11-octadecenoic acid Metabolite lipidmaps:LMFA02000278
11-Oxo-9(10)-EpOME Metabolite lipidmaps:LMFA02000406
10-KODA Metabolite lipidmaps:LMFA02000246
9(10)-EpOME Metabolite lipidmaps:LMFA02000037
10-HODA Metabolite lipidmaps:LMFA02000128
9(S)-HODE Metabolite lipidmaps:LMFA02000188
17-HODE Metabolite lipidmaps:LMFA02000399
Linoleic Acid Metabolite lipidmaps:LMFA01030120
9-KODE Metabolite lipidmaps:LMFA02000274
9(E),11(E)-ODEMangold's acid Metabolite lipidmaps:LMFA01030119
13-oxo-9(10)EpOME Metabolite lipidmaps:LMFA02000279
12(Z)-10-KOME Metabolite lipidmaps:LMFA02000055
13-KODE Metabolite lipidmaps:LMFA02000016
9,12,13-TRiHomes8 isomers Metabolite lipidmaps:LMFA02000169
9,10-DiHOME Metabolite lipidmaps:LMFA02000229
13(S)-HpODE Metabolite lipidmaps:LMFA02000034
10(E)-OME Metabolite lipidmaps:LMFA01030075
11-OH-9(10)-EpOME Metabolite lipidmaps:LMFA02000407
9-oxo-12(13)EpOME Metabolite lipidmaps:LMFA02000247
11(E)-10-HOME Metabolite lipidmaps:LMFA01050560
9OH-12,13-EpOME Metabolite lipidmaps:LMFA02000158
11OH-12,13-EpOME Metabolite lipidmaps:LMFA02000403
13-HODE(both forms) Metabolite lipidmaps:LMFA02000154
11(E)-10-KOME Metabolite lipidmaps:LMFA01060223
12,13-DiHOME Metabolite lipidmaps:LMFA02000230
12(Z)-10-HOME Metabolite lipidmaps:LMFA02000345
11-oxo-12(13)-EpOME Metabolite lipidmaps:LMFA02000404
11(S)-HODE Metabolite lipidmaps:LMFA02000401
9-HODE(both forms) Metabolite lipidmaps:LMFA02000151 Mixture of R and S LMFA02000036/LMFA02000188
9(Z)-OMEOleic Acid Metabolite lipidmaps:LMFA01030002
16-HODE Metabolite lipidmaps:LMFA02000405
9(R)-HpODE Metabolite lipidmaps:LMFA02000402
13(S)-HODE Metabolite lipidmaps:LMFA02000228
13(R)-HODE Metabolite lipidmaps:LMFA02000035
11(R)-HODE Metabolite lipidmaps:LMFA02000400
9,10,13-TriHOME8 isomers Metabolite lipidmaps:LMFA02000168
10(E),12(Z)-ODE Metabolite lipidmaps:LMFA01030125
12(13)-EpOME Metabolite lipidmaps:LMFA02000038
18-HODE Metabolite lipidmaps:LMFA02000398
9(Z)-11(E)-ODERumenic Acid Metabolite lipidmaps:LMFA01030118
13(S)-HODE Metabolite lipidmaps:LMFA02000228
9(R)-HODE Metabolite lipidmaps:LMFA02000036
13-OH-9(10)-EpOME Metabolite lipidmaps:LMFA02000278
CYP2C19 GeneProduct uniprot:P33261
ALOXE3 GeneProduct uniprot:Q9BYJ1
CYP1A2 GeneProduct uniprot:P05177
GPX4 GeneProduct uniprot:P36969
CYP3A4 GeneProduct uniprot:P08684
PGTS2 GeneProduct uniprot:PTGS2
ALOX12B GeneProduct uniprot:O75342
PGTS1 GeneProduct uniprot:P23219
CYP2C8 GeneProduct uniprot:P10632
CLA-HY GeneProduct uniprot:G9MAP1
CYP2C9 GeneProduct uniprot:P11712
CYP4A11 GeneProduct uniprot:Q02928
ALOX15 GeneProduct uniprot:P16050
CLA-HY GeneProduct uniprot:G9MAP1
CLA-HY GeneProduct uniprot:G9MAP1
CLA-HY GeneProduct uniprot:G9MAP1
EPHX3 GeneProduct uniprot:Q9H6B9
ALOXE3 GeneProduct uniprot:Q9BYJ1
GPX4 GeneProduct uniprot:P36969
ALOXE3 GeneProduct uniprot:Q9BYJ1
CYP2C9 GeneProduct uniprot:P11712
CYP2C9 GeneProduct uniprot:P11712

References

  1. Cytochromes P450 with bisallylic hydroxylation activity on arachidonic and linoleic acids studied with human recombinant enzymes and with human and rat liver microsomes. Bylund J, Kunz T, Valmsen K, Oliw EH. J Pharmacol Exp Ther. 1998 Jan;284(1):51–60. PubMed Europe PMC Scholia
  2. Stereochemistry of oxygenation of linoleic acid catalyzed by prostaglandin-endoperoxide H synthase-2. Hamberg M. Arch Biochem Biophys. 1998 Jan 15;349(2):376–80. PubMed Europe PMC Scholia
  3. Analysis of cytochrome P450 metabolites of arachidonic and linoleic acids by liquid chromatography-mass spectrometry with ion trap MS. Bylund J, Ericsson J, Oliw EH. Anal Biochem. 1998 Dec 1;265(1):55–68. PubMed Europe PMC Scholia
  4. Requirement for omega and (omega;-1)-hydroxylations of fatty acids by human cytochromes P450 2E1 and 4A11. Adas F, Salaün JP, Berthou F, Picart D, Simon B, Amet Y. J Lipid Res. 1999 Nov;40(11):1990–7. PubMed Europe PMC Scholia
  5. Lipoxygenases mediate the effect of essential fatty acid in skin barrier formation: a proposed role in releasing omega-hydroxyceramide for construction of the corneocyte lipid envelope. Zheng Y, Yin H, Boeglin WE, Elias PM, Crumrine D, Beier DR, et al. J Biol Chem. 2011 Jul 8;286(27):24046–56. PubMed Europe PMC Scholia
  6. EH3 (ABHD9): the first member of a new epoxide hydrolase family with high activity for fatty acid epoxides. Decker M, Adamska M, Cronin A, Di Giallonardo F, Burgener J, Marowsky A, et al. J Lipid Res. 2012 Oct;53(10):2038–45. PubMed Europe PMC Scholia
  7. Polyunsaturated fatty acid saturation by gut lactic acid bacteria affecting host lipid composition. Kishino S, Takeuchi M, Park SB, Hirata A, Kitamura N, Kunisawa J, et al. Proc Natl Acad Sci U S A. 2013 Oct 29;110(44):17808–13. PubMed Europe PMC Scholia
  8. A systems approach for discovering linoleic acid derivatives that potentially mediate pain and itch. Ramsden CE, Domenichiello AF, Yuan ZX, Sapio MR, Keyes GS, Mishra SK, et al. Sci Signal. 2017 Aug 22;10(493):eaal5241. PubMed Europe PMC Scholia
  9. The octadecanoids: an emerging class of lipid mediators. Quaranta A, Revol-Cavalier J, Wheelock CE. Biochem Soc Trans. 2022 Dec 16;50(6):1569–82. PubMed Europe PMC Scholia