Octadecanoid formation from linoleic acid (Homo sapiens)

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9755355375327565742555177155Gut bacteria, e.g. Lactiplantibacillus plantarum12(13)-EpOME10-KODA12(Z)-10-KOMELinoleic acidCLA-DH13-oxo-9(10)EpOMECYP4A119-oxo-12(13)EpOMECYP2C19PGTS1CYP3A413-KODE9(Z)-OMEOleic Acid16-HODE13(S)-HpODE13(S)-HODE10-HODA12(Z)-10-HOME9OH-12,13-EpOMEUnidentifieddehydrogenase(s)18-HODE9(R)-HpODE9(E),11(E)-ODEMangold's acid9(10)-EpOME9,10-DiHOMECYP2C99,10-epoxy-13-hydroxy-11-octadecenoic acid9(S)-HODE10(E)-OMEALOX1511(R)-HODE9(Z)-11(E)-ODERumenic AcidALOXE39,12,13-TRiHomes8 isomers9-HODE(both forms)CLA-ER11(S)-HODE11-Oxo-9(10)-EpOMECYP1A217-HODE9(R)-HODE9-KODE11-oxo-12(13)-EpOME9,10,13-TriHOME8 isomersGPX4PGTS211(E)-10-HOME12,13-DiHOME13(R)-HODECYP2C811OH-12,13-EpOMECLA-DC13(S)-HODE10(E),12(Z)-ODE13-HODE(both forms)ALOX12BCLA-HY11(E)-10-KOME11-OH-9(10)-EpOME83389(R)-HODE13-OH-9(10)-EpOMECLA-DHCLA-HYCLA-HYCLA-HYEPHX3ALOXE3GPX4ALOXE3CYP2C93CYP2C93Unidentifieddehydrogenase(s)Unidentifieddehydrogenase(s)


Description

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

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Quality Tags

Ontology Terms

 

Bibliography

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  1. Bylund J, Kunz T, Valmsen K, Oliw EH; ''Cytochromes P450 with bisallylic hydroxylation activity on arachidonic and linoleic acids studied with human recombinant enzymes and with human and rat liver microsomes.''; J Pharmacol Exp Ther, 1998 PubMed Europe PMC Scholia
  2. Zheng Y, Yin H, Boeglin WE, Elias PM, Crumrine D, Beier DR, Brash AR; ''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.''; J Biol Chem, 2011 PubMed Europe PMC Scholia
  3. Bylund J, Ericsson J, Oliw EH; ''Analysis of cytochrome P450 metabolites of arachidonic and linoleic acids by liquid chromatography-mass spectrometry with ion trap MS.''; Anal Biochem, 1998 PubMed Europe PMC Scholia
  4. Adas F, Salaün JP, Berthou F, Picart D, Simon B, Amet Y; ''Requirement for omega and (omega;-1)-hydroxylations of fatty acids by human cytochromes P450 2E1 and 4A11.''; J Lipid Res, 1999 PubMed Europe PMC Scholia
  5. Kishino S, Takeuchi M, Park SB, Hirata A, Kitamura N, Kunisawa J, Kiyono H, Iwamoto R, Isobe Y, Arita M, Arai H, Ueda K, Shima J, Takahashi S, Yokozeki K, Shimizu S, Ogawa J; ''Polyunsaturated fatty acid saturation by gut lactic acid bacteria affecting host lipid composition.''; Proc Natl Acad Sci U S A, 2013 PubMed Europe PMC Scholia
  6. Decker M, Adamska M, Cronin A, Di Giallonardo F, Burgener J, Marowsky A, Falck JR, Morisseau C, Hammock BD, Gruzdev A, Zeldin DC, Arand M; ''EH3 (ABHD9): the first member of a new epoxide hydrolase family with high activity for fatty acid epoxides.''; J Lipid Res, 2012 PubMed Europe PMC Scholia
  7. Hamberg M; ''Stereochemistry of oxygenation of linoleic acid catalyzed by prostaglandin-endoperoxide H synthase-2.''; Arch Biochem Biophys, 1998 PubMed Europe PMC Scholia
  8. Ramsden CE, Domenichiello AF, Yuan ZX, Sapio MR, Keyes GS, Mishra SK, Gross JR, Majchrzak-Hong S, Zamora D, Horowitz MS, Davis JM, Sorokin AV, Dey A, LaPaglia DM, Wheeler JJ, Vasko MR, Mehta NN, Mannes AJ, Iadarola MJ; ''A systems approach for discovering linoleic acid derivatives that potentially mediate pain and itch.''; Sci Signal, 2017 PubMed Europe PMC Scholia
  9. Quaranta A, Revol-Cavalier J, Wheelock CE; ''The octadecanoids: an emerging class of lipid mediators.''; Biochem Soc Trans, 2022 PubMed Europe PMC Scholia

History

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CompareRevisionActionTimeUserComment
134468view00:43, 22 July 2024EweitzFix placement for bacteria label, standardize case
126449view19:35, 30 April 2023AlexanderPicoModified description
126448view19:33, 30 April 2023AlexanderPicoModified title
125924view11:12, 20 March 2023Conroy lipidsadd unidentified DH to pathway
125505view11:00, 22 February 2023Conroy lipids
125504view09:01, 22 February 2023Conroy lipidsadd more enzymes
125498view13:56, 21 February 2023Conroy lipidsmore annotation added
125497view12:19, 21 February 2023Conroy lipidsa little more annotation
125382view16:38, 9 February 2023Conroy lipidsannotate reaction
125381view11:13, 9 February 2023Conroy lipidsOntology Term : 'linoleic acid metabolic pathway' added !
125380view11:12, 9 February 2023Conroy lipidsOntology Term : 'lipid signaling pathway' added !
125379view11:12, 9 February 2023Conroy lipidsOntology Term : 'lipid metabolic pathway' added !
125378view11:10, 9 February 2023Conroy lipidsNew pathway

External references

DataNodes

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NameTypeDatabase referenceComment
10(E),12(Z)-ODEMetaboliteLMFA01030125 (LIPID MAPS)
10(E)-OMEMetaboliteLMFA01030075 (LIPID MAPS)
10-HODAMetaboliteLMFA02000128 (LIPID MAPS)
10-KODAMetaboliteLMFA02000246 (LIPID MAPS)
11(E)-10-HOMEMetaboliteLMFA01050560 (LIPID MAPS)
11(E)-10-KOMEMetaboliteLMFA01060223 (LIPID MAPS)
11(R)-HODEMetaboliteLMFA02000400 (LIPID MAPS)
11(S)-HODEMetaboliteLMFA02000401 (LIPID MAPS)
11-OH-9(10)-EpOMEMetaboliteLMFA02000407 (LIPID MAPS)
11-Oxo-9(10)-EpOMEMetaboliteLMFA02000406 (LIPID MAPS)
11-oxo-12(13)-EpOMEMetaboliteLMFA02000404 (LIPID MAPS)
11OH-12,13-EpOMEMetaboliteLMFA02000403 (LIPID MAPS)
12(13)-EpOMEMetaboliteLMFA02000038 (LIPID MAPS)
12(Z)-10-HOMEMetaboliteLMFA02000345 (LIPID MAPS)
12(Z)-10-KOMEMetaboliteLMFA02000055 (LIPID MAPS)
12,13-DiHOMEMetaboliteLMFA02000230 (LIPID MAPS)
13(R)-HODEMetaboliteLMFA02000035 (LIPID MAPS)
13(S)-HODEMetaboliteLMFA02000228 (LIPID MAPS)
13(S)-HpODEMetaboliteLMFA02000034 (LIPID MAPS)
13-HODE (both forms)MetaboliteLMFA02000154 (LIPID MAPS)
13-KODEMetaboliteLMFA02000016 (LIPID MAPS)
13-OH-9(10)-EpOMEMetaboliteLMFA02000278 (LIPID MAPS)
13-oxo-9(10)EpOMEMetaboliteLMFA02000279 (LIPID MAPS)
16-HODEMetaboliteLMFA02000405 (LIPID MAPS)
17-HODEMetaboliteLMFA02000399 (LIPID MAPS)
18-HODEMetaboliteLMFA02000398 (LIPID MAPS)
9(10)-EpOMEMetaboliteLMFA02000037 (LIPID MAPS)
9(E),11(E)-ODE Mangold's acidMetaboliteLMFA01030119 (LIPID MAPS)
9(R)-HODEMetaboliteLMFA02000036 (LIPID MAPS)
9(R)-HpODEMetaboliteLMFA02000402 (LIPID MAPS)
9(S)-HODEMetaboliteLMFA02000188 (LIPID MAPS)
9(Z)-11(E)-ODE Rumenic AcidMetaboliteLMFA01030118 (LIPID MAPS)
9(Z)-OME Oleic AcidMetaboliteLMFA01030002 (LIPID MAPS)
9,10,13-TriHOME 8 isomersMetaboliteLMFA02000168 (LIPID MAPS)
9,10-DiHOMEMetaboliteLMFA02000229 (LIPID MAPS)
9,10-epoxy-13-hydroxy-11-octadecenoic acidMetaboliteLMFA02000278 (LIPID MAPS)
9,12,13-TRiHomes 8 isomersMetaboliteLMFA02000169 (LIPID MAPS)
9-HODE (both forms)MetaboliteLMFA02000151 (LIPID MAPS) Mixture of R and S LMFA02000036/LMFA02000188
9-KODEMetaboliteLMFA02000274 (LIPID MAPS)
9-oxo-12(13)EpOMEMetaboliteLMFA02000247 (LIPID MAPS)
9OH-12,13-EpOMEMetaboliteLMFA02000158 (LIPID MAPS)
ALOX12BGeneProductO75342 (Uniprot-TrEMBL)
ALOX15GeneProductP16050 (Uniprot-TrEMBL)
ALOXE3GeneProductQ9BYJ1 (Uniprot-TrEMBL)
CLA-DCGeneProduct
CLA-DHGeneProduct
CLA-ERGeneProduct
CLA-HYGeneProductG9MAP1 (Uniprot-TrEMBL)
CYP1A2GeneProductP05177 (Uniprot-TrEMBL)
CYP2C19GeneProductP33261 (Uniprot-TrEMBL)
CYP2C8GeneProductP10632 (Uniprot-TrEMBL)
CYP2C9GeneProductP11712 (Uniprot-TrEMBL)
CYP3A4GeneProductP08684 (Uniprot-TrEMBL)
CYP4A11GeneProductQ02928 (Uniprot-TrEMBL)
EPHX3GeneProductQ9H6B9 (Uniprot-TrEMBL)
GPX4GeneProductP36969 (Uniprot-TrEMBL)
Linoleic acidMetaboliteLMFA01030120 (LIPID MAPS)
PGTS1GeneProductP23219 (Uniprot-TrEMBL)
PGTS2GeneProductPTGS2 (Uniprot-TrEMBL)
Unidentified dehydrogenase(s)GeneProduct

Annotated Interactions

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SourceTargetTypeDatabase referenceComment
12(13)-EpOME12,13-DiHOMEmim-conversion44037 (Rhea)
13(S)-HODE13-KODEmim-conversion48717 (Rhea)
13(S)-HpODE11OH-12,13-EpOMEmim-conversion50213 (Rhea) EC:5.4.4.7
13(S)-HpODE13(S)-HODEmim-conversion48889 (Rhea) EC:1.11.1.12
9(10)-EpOME9,10-DiHOMEmim-conversion44033 (Rhea) EC:3.3.2.10
Linoleic acid11(R)-HODEmim-conversion52285 (Rhea) EC:1.14.14.1
Linoleic acid11(S)-HODEmim-conversion18994 (Rhea) EC:1.13.11.45
Linoleic acid13(R)-HODEmim-conversion75455 (Rhea) EC:1.14.99.1
Linoleic acid13(S)-HODEmim-conversion75451 (Rhea) EC:1.14.99.1
Linoleic acid13(S)-HpODEmim-conversion22781 (Rhea) EC:1.13.1.12
Linoleic acid13-HODE (both forms)mim-conversion50861 (Rhea) EC:1.14.99.1
Linoleic acid17-HODEmim-conversion60933 (Rhea) EC:1.14.14.80
Linoleic acid18-HODEmim-conversion60581 (Rhea) EC:1.14.14.80
Linoleic acid9(R)-HODEmim-conversion75447 (Rhea) EC:1.14.99.1
Linoleic acid9(S)-HODEmim-conversion75459 (Rhea) EC:1.14.99.1
Linoleic acid9-HODE (both forms)mim-conversion50865 (Rhea) EC:1.14.99.1
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