Eicosanoid metabolism via cyclooxygenases (COX) (Mus musculus)

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14523425443PtgisPGB2PGC2SpontaneousPla2g5GlycerophospholipidsPPAR delta44Arachidonic acid2, 5Pla2g6Pla2g4aPla2g4bPtgs1Ptgs2PGG2PGH2PGE24Ptges4PGF2a4PGD2PGJ22delta-12-PGJ215-deoxy-delta-12-PGD222Ptgds411R-HETE5PGI246-keto-PGF1alpha6-keto-PGE1PGA215-deoxy-PGA2Akr1b3Dinor-PGE2Tetranor-PGE2Dinor-PGF2aTetranor-PGF2aDinor-PGD2Tetranor-PGD220-hydroxy-PGE220-hydroxy-PGF2a520-hydroxy-PGD215-deoxy-delta-12-PGJ2TXA2TXB2411-dehydro-TXB212S-HHTrETbxas12Txdh15-keto-PGE215-keto-PGF2a415-keto-PGD213,14-dihydro-15-keto-PGE213,14-dihydro-15-keto-PGF2a13,14-dihydro-15-keto-PGD2Ptgr1Ptgr2HpgdCyp4a10Cyp4a12aCyp4a12bCyp4f14Cyp4f18HpgdAcox14Acox2Acox3Acaa1aEhhadhIP4PPAR gamma444PGFS4FP44PPAR gamma444DP1DP24444TP44COX-1515(S)-HETE15(R)-HETE55AAS55COX-155AAS55


Description

This pathway is inspired by the Lipidmaps>Eicosanoids Pathway expended pathway display [1] and extended with the top left side of Figure 1 from Dennis and Norris (2015 [2]).

Eicosanoids are a large group of compounds metabolised from arachidonic acid (AA), either via cyclooxygenases (COX)[3], lipooxygenases(LOX)[4], or cytochrome P450 monooxygenases (CYP)[5]. This pathway visualises the first route, via COX, where additonal colours have been used to visualise which conversions are being performed by the same enzymes.

Green and orange boxes represent receptors, where the orange colour depicts peroxisome-proliferator activating receptors (PPARs) potentially activated by the eicosanoids.

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Ontology Terms

 

Bibliography

  1. Dennis EA, Deems RA, Harkewicz R, Quehenberger O, Brown HA, Milne SB, Myers DS, Glass CK, Hardiman G, Reichart D, Merrill AH Jr, Sullards MC, Wang E, Murphy RC, Raetz CR, Garrett TA, Guan Z, Ryan AC, Russell DW, McDonald JG, Thompson BM, Shaw WA, Sud M, Zhao Y, Gupta S, Maurya MR, Fahy E, Subramaniam S; ''A mouse macrophage lipidome.''; J Biol Chem, 2010 PubMed Europe PMC Scholia
  2. Dennis EA, Norris PC; ''Eicosanoid storm in infection and inflammation.''; Nat Rev Immunol, 2015 PubMed Europe PMC Scholia
  3. Polet H, Levine L; ''Metabolism of prostaglandins E, A, and C in serum.''; J Biol Chem, 1975 PubMed Europe PMC Scholia
  4. Dennis EA, Norris PC; ''Eicosanoid storm in infection and inflammation.''; Nat Rev Immunol, 2015 PubMed Europe PMC Scholia
  5. Moreno JJ; ''New aspects of the role of hydroxyeicosatetraenoicacids in cell growth and cancer development.''; Biochem Pharmacol, 2009 PubMed Europe PMC Scholia

History

View all...
CompareRevisionActionTimeUserComment
124982view13:03, 11 January 2023Conroy lipidssort TXA2->B2 spontaneous conversion
124966view15:01, 10 January 2023Conroy lipidsadd more rhea cross refs, make bold mim-conversion lacking Rhea
124965view12:26, 10 January 2023Conroy lipidsadd some Rhea, correct lipid ID, make multi-step reactions dotted
124742view08:49, 8 December 2022DeSlUpdated link to LIPID MAPS PWs.
124346view14:37, 18 October 2022Conroy lipidsmore rheas
124345view13:05, 18 October 2022Conroy lipidsadd rheas, convert arrows to mim-conversion. Beginning only
116511view10:45, 7 May 2021EweitzModified title
110702view14:11, 28 May 2020EgonwAdded missing @Type annotation
106328view08:40, 21 August 2019DeSlTrying to fix empty lit ref in GPML now.
106327view08:38, 21 August 2019DeSlTrying to fix empty lit. ref.
106326view08:32, 21 August 2019DeSlAdded general LipidMaps publication.
106271view14:30, 19 August 2019DeSlModified description
102928view12:59, 29 January 2019DeSlAdded additional info from last lit. ref
102922view12:40, 29 January 2019DeSlAdded last details of second lit. ref
102920view12:37, 29 January 2019DeSlAdded info from second lit. ref.
102915view12:09, 28 January 2019DeSlChanged layout to reflect content of LipidMaps better.
102912view12:00, 28 January 2019DeSlModified description
102881view15:45, 25 January 2019DeSlModified description
102874view15:37, 25 January 2019DeSlOntology Term : 'cyclooxygenase mediated pathway of arachidonic acid metabolism' added !
102873view15:37, 25 January 2019DeSlOntology Term : 'arachidonic acid metabolic pathway' added !
102872view15:36, 25 January 2019DeSlOntology Term : 'PW:0000002' removed !
102871view15:36, 25 January 2019DeSlOntology Term : 'eicosanoid biosynthetic pathway' added !
102870view15:36, 25 January 2019DeSlOntology Term : 'eicosanoid signaling pathway via peroxisome proliferator-activated receptor gamma' added !
102869view15:36, 25 January 2019DeSlOntology Term : 'eicosanoid signaling pathway' added !
102868view15:36, 25 January 2019DeSlOntology Term : 'eicosanoid metabolic pathway' added !
102867view15:35, 25 January 2019DeSlAdded all receptor interactions from lit. ref.
102866view15:24, 25 January 2019DeSlChanged colour of third eicosanoid group from green to purple, to enable green boxes for receptors (as in the lit. ref)
102865view15:21, 25 January 2019DeSlModified description
102864view15:19, 25 January 2019DeSlModified description
102863view15:17, 25 January 2019DeSlAdded information from Lit. ref [26139350].
102850view11:59, 25 January 2019DeSlAdded more colours to clarify which enzymes is performing conversions for different groups.
102849view11:53, 25 January 2019DeSlAdded colours for corssing enzyme catalysis lines.
102848view11:50, 25 January 2019DeSlMore layout changes
102847view11:04, 25 January 2019DeSlFirst layout changes
102846view10:47, 25 January 2019DeSlModified title
102845view10:46, 25 January 2019DeSlModified description
98609view12:41, 21 September 2018RyanmillerOntology Term : 'classic metabolic pathway' added !
98577view15:54, 17 September 2018EoinfahyNew pathway

External references

DataNodes

View all...
NameTypeDatabase referenceComment
11-dehydro-TXB2MetaboliteLMFA03030004 (LIPID MAPS)
11R-HETEMetaboliteLMFA03060028 (LIPID MAPS)
12S-HHTrEMetaboliteLMFA03050002 (LIPID MAPS)
13,14-dihydro- 15-keto-PGD2MetaboliteLMFA03010022 (LIPID MAPS)
13,14-dihydro- 15-keto-PGE2MetaboliteLMFA03010031 (LIPID MAPS)
13,14-dihydro- 15-keto-PGF2aMetaboliteLMFA03010027 (LIPID MAPS)
15(R)-HETEMetaboliteLMFA03060030 (LIPID MAPS)
15(S)-HETEMetaboliteLMFA03060001 (LIPID MAPS)
15-deoxy-PGA2MetaboliteLMFA03010172 (LIPID MAPS)
15-deoxy-delta-12-PGD2MetaboliteLMFA03010021 (LIPID MAPS)
15-deoxy-delta-12-PGJ2MetaboliteLMFA03010021 (LIPID MAPS)
15-keto-PGD2MetaboliteLMFA03010022 (LIPID MAPS)
15-keto-PGE2MetaboliteLMFA03010030 (LIPID MAPS)
15-keto-PGF2aMetaboliteLMFA03010026 (LIPID MAPS)
20-hydroxy-PGD2MetaboliteLMFA03010216 (LIPID MAPS)
20-hydroxy-PGE2MetaboliteLMFA03010014 (LIPID MAPS)
20-hydroxy-PGF2aMetaboliteLMFA03010029 (LIPID MAPS)
6-keto-PGE1MetaboliteLMFA03010012 (LIPID MAPS)
6-keto-PGF1alphaMetaboliteLMFA03010001 (LIPID MAPS)
AASProtein
Acaa1aProtein113868 (Entrez Gene)
Acox1Protein11430 (Entrez Gene)
Acox2Protein93732 (Entrez Gene)
Acox3Protein80911 (Entrez Gene)
Akr1b3Protein11677 (Entrez Gene)
Arachidonic acidMetaboliteLMFA01030001 (LIPID MAPS)
COX-1ProteinP22437 (Uniprot-TrEMBL)
Cyp4a10Protein13117 (Entrez Gene)
Cyp4a12aProtein277753 (Entrez Gene)
Cyp4a12bProtein13118 (Entrez Gene)
Cyp4f14Protein64385 (Entrez Gene)
Cyp4f18Protein72054 (Entrez Gene)
DP1ProteinP70263 (Uniprot-TrEMBL) AKA Prostaglandin D2 receptor 1 (DP1) [https://en.wikipedia.org/wiki/Prostaglandin_DP1_receptor]
DP2ProteinQ9Z2J6 (Uniprot-TrEMBL) AKA Prostaglandin D2 receptor 2 (DP2 or CRTH2) [https://en.wikipedia.org/wiki/Prostaglandin_DP2_receptor]
Dinor-PGD2MetaboliteLMFA03010214 (LIPID MAPS)
Dinor-PGE2MetaboliteLMFA03010210 (LIPID MAPS)
Dinor-PGF2aMetaboliteLMFA03010212 (LIPID MAPS)
EhhadhProtein74147 (Entrez Gene)
FPProteinP43117 (Uniprot-TrEMBL) AKA Prostaglandin F receptor (FP) [https://en.wikipedia.org/wiki/Prostaglandin_F_receptor]
GlycerophospholipidsMetaboliteCHEBI:37739 (ChEBI)
HpgdGeneProduct15446 (Entrez Gene)
IPProteinP43252 (Uniprot-TrEMBL) AKA Prostacyclin receptor, prostaglandin I2 receptor or just IP [https://en.wikipedia.org/wiki/Prostacyclin_receptor]
PGA2MetaboliteLMFA03010035 (LIPID MAPS)
PGB2MetaboliteLMFA03010018 (LIPID MAPS)
PGC2MetaboliteLMFA03010133 (LIPID MAPS)
PGD2MetaboliteLMFA03010004 (LIPID MAPS)
PGE2MetaboliteLMFA03010003 (LIPID MAPS)
PGF2aMetaboliteLMFA03010002 (LIPID MAPS)
PGFSProteinQ9DB60 (Uniprot-TrEMBL) AKA Prxl2b
PGG2MetaboliteLMFA03010009 (LIPID MAPS)
PGH2MetaboliteLMFA03010010 (LIPID MAPS)
PGI2MetaboliteLMFA03010087 (LIPID MAPS)
PGJ2MetaboliteLMFA03010019 (LIPID MAPS)
PPAR deltaProteinP35396 (Uniprot-TrEMBL) AKA Peroxisome proliferator-activated receptor delta
PPAR gammaProteinP37238 (Uniprot-TrEMBL) AKA Peroxisome proliferator-activated receptor gamma
Pla2g4aProtein18783 (Entrez Gene)
Pla2g4bProtein211429 (Entrez Gene)
Pla2g5Protein18784 (Entrez Gene)
Pla2g6Protein53357 (Entrez Gene)
PtgdsProtein19215 (Entrez Gene)
PtgesProtein64292 (Entrez Gene)
PtgisGeneProduct19223 (Entrez Gene)
Ptgr1Protein67103 (Entrez Gene)
Ptgr2Protein77219 (Entrez Gene)
Ptgs1Protein19224 (Entrez Gene) AKA COX-1
Ptgs2Protein19225 (Entrez Gene) AKA COX-2
Spontaneous
TPProteinP30987 (Uniprot-TrEMBL) AKA thromboxane receptor (TP) also known as the prostanoid TP receptor [https://en.wikipedia.org/wiki/Thromboxane_receptor]
TXA2MetaboliteLMFA03030001 (LIPID MAPS)
TXB2MetaboliteLMFA03030002 (LIPID MAPS)
Tbxas1GeneProduct21391 (Entrez Gene)
Tetranor-PGD2MetaboliteLMFA03010215 (LIPID MAPS)
Tetranor-PGE2MetaboliteLMFA03010211 (LIPID MAPS)
Tetranor-PGF2aMetaboliteLMFA03010213 (LIPID MAPS)
TxdhGeneProduct
delta-12-PGJ2MetaboliteLMFA03010020 (LIPID MAPS)

Annotated Interactions

View all...
SourceTargetTypeDatabase referenceComment
15-keto-PGE213,14-dihydro- 15-keto-PGE2mim-conversion11914 (Rhea)
Arachidonic acid11R-HETEmim-conversion50853 (Rhea)
Arachidonic acidPGG2mim-conversion42597 (Rhea)
PGA2PGC2mim-conversion50541 (Rhea)
PGC2PGB2mim-conversion50545 (Rhea)
PGD2PGJ2mim-conversion50557 (Rhea)
PGE220-hydroxy-PGE2mim-conversion52489 (Rhea)
PGE2PGA2mim-conversion50537 (Rhea)
PGE2mim-conversion11877 (Rhea)
PGG2PGH2mim-conversion42601 (Rhea)
PGH212S-HHTrEmim-conversion48645 (Rhea)
PGH2PGD2mim-conversion10601 (Rhea)
PGH2PGE2mim-conversion12894 (Rhea)
PGH2PGF2amim-conversion45314 (Rhea)
PGH2PGI2mim-conversion23581 (Rhea)
PGH2mim-conversion17138 (Rhea)
PGH2mim-conversion28215 (Rhea)
PGJ2delta-12-PGJ2mim-conversion53549 (Rhea)
TXB211-dehydro-TXB2mim-conversion52313 (Rhea)
Retrieved from "https://classic.wikipathways.org/index.php/Pathway:WP4347"
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