(5Z,8Z,11Z,14Z)-eicosatetraenoate

Three steps

• glyoxylateReach from here →
  1. N-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-glycine + H2O = (5Z,8Z,11Z,14Z)-eicosatetraenoate + glycine
  2. N-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-glycine + H2O = (5Z,8Z,11Z,14Z)-eicosatetraenoate + glycine
  3. glycine + 2-oxoglutarate = glyoxylate + L-glutamate

  Catalysed by FAAH, PM20D1, AADATOne of 11 routes

• a 1-O-alkyl-2-acyl-sn-glycero-3-phosphocholineReach from here →
  1. Arachidonate:CoA ligase (AMP-forming)
  2. acyl-CoA pool formation and breakdown
  3. Acyl-CoA:1-alkyl-sn-glycero-3-phosphocholine O-acyltransferase

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 8 morecytosol

• CHEBI:37946Reach from here →
  1. transport of arachidonate (cytosol to extracellular)
  2. transport of dopamine (cytosol to extracellular)
  3. aryl sulfotransferase (dopamine)

  Catalysed by SLCO1B1, SLCO1A2, SLCO1B3, SULT1A3 and 3 moreextracellular space, cytosol

• L-2-amino-3-oxobutanoic acidReach from here →
  1. N-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-glycine + H2O = (5Z,8Z,11Z,14Z)-eicosatetraenoate + glycine
  2. N-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-glycine + H2O = (5Z,8Z,11Z,14Z)-eicosatetraenoate + glycine
  3. Acetyl-CoA:glycine C-acetyltransferase

  Catalysed by FAAH, PM20D1, GCATmitochondrial matrix

• (R)-lactic acidReach from here →
  1. transport of arachidonate and GSH (cytosol to extracellular)
  2. (R)-S-Lactoylglutathione methylglyoxal-lyase (isomerizing)
  3. (R)-S-Lactoylglutathione hydrolase

  Catalysed by GLO1, GLOD4, HAGH, HAGHLextracellular space, cytosolOne of 2 routes

• (S)-lactic acidReach from here →
  1. transport of arachidonate (cytosol to extracellular)
  2. transport of prostaglandin A2 (cytosol to extracellular)
  3. Transport of Prostaglandin A2, Lactate Antiport

  Catalysed by SLCO1B1extracellular space, cytosolOne of 4 routes

• 25-hydroxycholesterolReach from here →
  1. (5Z,8Z,11Z,14Z)-eicosatetraenoate + AH2 + 2 O2 = prostaglandin H2 + A + H2O
  2. A + NADH + H(+) = AH2 + NAD(+)
  3. cholesterol + AH2 + O2 = 25-hydroxycholesterol + A + H2O

  Catalysed by PTGS1, PTGS2, AIFM1, PYROXD1 and 1 more

• all-trans-4-oxoretinolReach from here →
  1. (5Z,8Z,11Z,14Z)-eicosatetraenoate + AH2 + 2 O2 = prostaglandin H2 + A + H2O
  2. all-trans-13,14-dihydroretinol + A = all-trans-retinol + AH2
  3. cytochrome P450 (retinol)

  Catalysed by PTGS1, PTGS2, RETSAT, CYP26A1cytosol

• phosphoenolpyruvic acidReach from here →
  1. (5Z,8Z,11Z,14Z)-eicosatetraenoate + AH2 + 2 O2 = prostaglandin H2 + A + H2O
  2. (R)-malate + A = oxaloacetate + AH2
  3. GTP:oxaloacetate carboxy-lyase (adding GTP

  Catalysed by PTGS1, PTGS2, D2HGDH, PCK1cytosolOne of 2 routes

• 13-cis-retinolReach from here →
  1. (5Z,8Z,11Z,14Z)-eicosatetraenoate + AH2 + 2 O2 = prostaglandin H2 + A + H2O
  2. all-trans-13,14-dihydroretinol + A = all-trans-retinol + AH2
  3. retinol binding protein (retinol)

  Catalysed by PTGS1, PTGS2, RETSAT, RBP1 and 1 morecytosolOne of 2 routes

• L-ornithineReach from here →
  1. transport of arachidonate and GSH (cytosol to extracellular)
  2. cystine to cysteine conversion
  3. transport of cysteine and ornithine (cytosol to extracellular)

  Catalysed by SLC7A6extracellular space, cytosolOne of 9 routes

• a 1,3-diacylglycerolReach from here →
  1. Arachidonate:CoA ligase (AMP-forming)
  2. acyl-CoA pool formation and breakdown
  3. a 1-acylglycerol + an acyl-CoA = a 1,3-diacylglycerol + CoA

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 6 morecytosol

• N-methylserotoninReach from here →
  1. transport of arachidonate (cytosol to extracellular)
  2. transport of serotonin (cytosol to extracellular)
  3. S-Adenosyl-L-methionine:amine N-methyltransferase

  Catalysed by SLCO1B1, SLCO1A2, SLCO1B3, INMTextracellular space, cytosol

• a 1,2-diacylglycerolReach from here →
  1. Arachidonate:CoA ligase (AMP-forming)
  2. acyl-CoA pool formation and breakdown
  3. a 2-acylglycerol + an acyl-CoA = a 1,2-diacylglycerol + CoA

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 9 morecytosolOne of 2 routes

• (5-hydroxyindol-3-yl)acetaldehydeReach from here →
  1. transport of arachidonate (cytosol to extracellular)
  2. transport of serotonin (cytosol to extracellular)
  3. 5-Hydroxytryptamine:oxygen oxidoreductase(deaminating)(flavin-containing)

  Catalysed by SLCO1B1, SLCO1A2, SLCO1B3, MAOA and 1 moreextracellular space, cytosolOne of 2 routes

• S(8)-aminomethyldihydrolipoamideReach from here →
  1. N-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-glycine + H2O = (5Z,8Z,11Z,14Z)-eicosatetraenoate + glycine
  2. N-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-glycine + H2O = (5Z,8Z,11Z,14Z)-eicosatetraenoate + glycine
  3. dihydrolipoyl dehydrogenase ([protein]-N6-(lipoyl)lysine)

  Catalysed by FAAH, PM20D1, GLDC, GCSHmitochondrial matrix

• taurineReach from here →
  1. Arachidonate:CoA ligase (AMP-forming)
  2. Arachidonyl-CoA hydrolase
  3. bile acid-CoA:amino acid N-acyltransferase (taurodeoxycholate)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 9 morecytosolOne of 4 routes

• all-trans-13,14-dihydroretinolReach from here →
  1. (5Z,8Z,11Z,14Z)-eicosatetraenoate + AH2 + 2 O2 = prostaglandin H2 + A + H2O
  2. A + NADH + H(+) = AH2 + NAD(+)
  3. all-trans-13,14-dihydroretinol + A = all-trans-retinol + AH2

  Catalysed by PTGS1, PTGS2, AIFM1, PYROXD1 and 1 moreOne of 2 routes

• an N-acylsphing-4-enineReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. N-acylsphingosine amidohydrolase
  3. delta 4-desaturase, sphingolipid (dihydroceramide pool)

  Catalysed by ASAH1, ACER2, ACER1, ASAH2 and 3 morecytosolOne of 5 routes

• 1,2,3-tri-(9Z-octadecenoyl)-glycerolReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. 1,2-di-(9Z-octadecenoyl)-glycerol + (9Z)-octadecenoate + H(+) = 1,2,3-tri-(9Z-octadecenoyl)-glycerol + H2O

  Catalysed by DGAT1, LIPA, PNPLA4, LIPE and 1 morecytosol, extracellular space

• 16-hydroxyhexadecanoateReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. Fatty Acid Omega Oxidation (C16->W-Ohc16), Endoplasmatic Reticulum

  Catalysed by CYP4F2, CYP4F3cytosol, extracellular space, endoplasmic reticulumOne of 2 routes

• 3,3',5'-triiodo-L-thyronineReach from here →
  1. transport of arachidonate (cytosol to extracellular)
  2. transport of S-glutathionyl-2-4-dinitrobenzene (cytosol to extracellular)
  3. 3,3',5'-triiodo-L-thyronine + iodide + A + H(+) = L-thyroxine + AH2

  Catalysed by SLCO1B1, SLCO1A2, SLCO1B3, DIO1 and 1 moreextracellular space, cytosolOne of 2 routes

• a 1,2-diacyl-sn-glycero-3-phospho-L-serineReach from here →
  1. Arachidonate:CoA ligase (AMP-forming)
  2. acyl-CoA pool formation and breakdown
  3. a 1-acyl-sn-glycero-3-phospho-L-serine + an acyl-CoA = a 1,2-diacyl-sn-glycero-3-phospho-L-serine + CoA

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 7 morecytosol

• (R)-methylmalonyl-CoAReach from here →
  1. Arachidonate:CoA ligase (AMP-forming)
  2. Arachidonyl-CoA hydrolase
  3. aldehyde dehydrogenase (2-methyl-3-oxopropanoate)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 10 morecytosol, mitochondrial matrixOne of 2 routes

• (S)-methylmalonyl-CoAReach from here →
  1. Arachidonate:CoA ligase (AMP-forming)
  2. Arachidonyl-CoA hydrolase
  3. (S)-methylmalonyl-CoA hydrolase

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 9 morecytosol, mitochondrial matrixOne of 2 routes

• 3'-dephospho-CoAReach from here →
  1. Arachidonate:CoA ligase (AMP-forming)
  2. Arachidonyl-CoA hydrolase
  3. acid phosphatase 2, lysosomal (CoA)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 10 morecytosol, lysosomeOne of 2 routes

• (2E)-dodecenoyl-CoAReach from here →
  1. Arachidonate:CoA ligase (AMP-forming)
  2. Arachidonyl-CoA hydrolase
  3. (2E)-dodecenoyl-CoA formation

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 9 morecytosol, mitochondrial matrixOne of 3 routes

• (2E)-butenoyl-CoAReach from here →
  1. Utilized Transport
  2. transport of butyryl-CoA and L-carnitine (cytosol to mitochondria)
  3. butanoyl-CoA:electron-transfer flavoprotein 2,3-oxidoreductase

  Catalysed by SLC33A1, ESCO2, OXSM, ACADS and 1 moreendoplasmic reticulum, cytosol, mitochondrial matrixOne of 2 routes

• 4,8,12-trimethyltridecanoyl-CoAReach from here →
  1. Arachidonate:CoA ligase (AMP-forming)
  2. Arachidonyl-CoA hydrolase
  3. propanoyl-CoA C-acyltransferase (3-ketopristanoyl-CoA)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 11 morecytosol, peroxisomeOne of 2 routes

• (6Z,9Z,12Z)-octadecatrienoyl-CoAReach from here →
  1. Arachidonate:CoA ligase (AMP-forming)
  2. Arachidonyl-CoA hydrolase
  3. long-chain-fatty-acid-CoA ligase (gamma-linolenate)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 9 morecytosolOne of 9 routes

• acryloyl-CoAReach from here →
  1. Utilized Transport
  2. Active Transport
  3. medium-chain acyl-CoA dehydrogenase (propanoyl-CoA)

  Catalysed by ACADS, ACADSBendoplasmic reticulum, cytosol, mitochondrial matrix

• choloyl-CoAReach from here →
  1. transport of arachidonate (cytosol to extracellular)
  2. solute carrier organic anion transporter (cholate)
  3. cholate + ATP + CoA = choloyl-CoA + AMP + diphosphate

  Catalysed by SLCO1B1, SLCO1A2, SLCO1B3, SLC27A5extracellular space, cytosol

• dodecanoyl-CoAReach from here →
  1. Arachidonate:CoA ligase (AMP-forming)
  2. Arachidonyl-CoA hydrolase
  3. long-chain-fatty-acid-CoA ligase (lauric acid)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 9 morecytosolOne of 17 routes

• glutaryl-CoAReach from here →
  1. Arachidonate:CoA ligase (AMP-forming)
  2. Arachidonyl-CoA hydrolase
  3. Production of Glutaryl Carnitine

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 12 morecytosolOne of 2 routes

• hexadecanoyl-CoAReach from here →
  1. Utilized Transport
  2. palmitoyl-CoA:L-carnitine O-palmitoyltransferase
  3. (R)-carnitine + hexadecanoyl-CoA = O-hexadecanoyl-(R)-carnitine + CoA

  Catalysed by CPT2, CPT1A, CPT1Bendoplasmic reticulum, cytosol, peroxisome

• eicosanoyl-CoAReach from here →
  1. Arachidonate:CoA ligase (AMP-forming)
  2. Arachidonyl-CoA hydrolase
  3. long-chain-fatty-acid-CoA ligase (eicosanoate)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 9 morecytosolOne of 19 routes

• itaconyl-CoAReach from here →
  1. Arachidonate:CoA ligase (AMP-forming)
  2. Arachidonyl-CoA hydrolase
  3. Itaconate:CoA ligase (GDP-forming)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 12 morecytosol, mitochondrial matrixOne of 2 routes

• (9Z,12Z)-octadecadienoyl-CoAReach from here →
  1. Arachidonate:CoA ligase (AMP-forming)
  2. Arachidonyl-CoA hydrolase
  3. long-chain-fatty-acid-CoA ligase ((6Z,9Z)-octadecadienoic acid)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 9 morecytosolOne of 19 routes

• tetradecanoyl-CoAReach from here →
  1. Arachidonate:CoA ligase (AMP-forming)
  2. Arachidonyl-CoA hydrolase
  3. long-chain-fatty-acid-CoA ligase (myristic acid)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 9 morecytosolOne of 16 routes

• octanoyl-CoAReach from here →
  1. Arachidonate:CoA ligase (AMP-forming)
  2. Arachidonyl-CoA hydrolase
  3. Octanoyl-CoA:L-carnitine O-octanoyltransferase

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 10 morecytosol, mitochondrial matrixOne of 23 routes

• (9Z)-octadecenoyl-CoAReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. (9Z)-octadecenoate + ATP + CoA = (9Z)-octadecenoyl-CoA + AMP + diphosphate

  Catalysed by SLC27A2, ACSL3, ACSL1, ACSBG2 and 4 morecytosol, extracellular space

• phytanoyl-CoAReach from here →
  1. Arachidonate:CoA ligase (AMP-forming)
  2. Arachidonyl-CoA hydrolase
  3. phytanate-CoA ligase

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 9 morecytosolOne of 5 routes

• octadecanoyl-CoAReach from here →
  1. Arachidonate:CoA ligase (AMP-forming)
  2. Arachidonyl-CoA hydrolase
  3. long-chain-fatty-acid-CoA ligase (stearate)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 9 morecytosolOne of 23 routes

• 15-oxoprostaglandin E2Reach from here →
  1. transport of arachidonate (cytosol to extracellular)
  2. transport of prostaglandin E2 (cytosol to extracellular)
  3. prostaglandin E2 + NAD(+) = 15-oxoprostaglandin E2 + NADH + H(+)

  Catalysed by SLCO1B1, SLCO1A2, SLCO1B3, HPGDextracellular space, cytosolOne of 2 routes

• 15-oxoprostaglandin E1Reach from here →
  1. transport of arachidonate (cytosol to extracellular)
  2. transport of prostaglandin E1 (cytosol to extracellular)
  3. (13E)-(15S)-11alpha,15-dihydroxy-9-oxoprost-13-enoate:NADP+ 15-oxidoreductase

  Catalysed by SLCO1B1, CBR3, CBR1, DHRS4extracellular space, cytosolOne of 3 routes

• 15-oxoprostaglandin D2Reach from here →
  1. transport of arachidonate (cytosol to extracellular)
  2. transport of prostaglandin D2 (cytosol to extracellular)
  3. 15-dehydro-prostaglandin D2 reduction

  Catalysed by SLCO1B1extracellular space, cytosolOne of 2 routes

• sarcosineReach from here →
  1. (5Z,8Z,11Z,14Z)-eicosatetraenoate + AH2 + 2 O2 = prostaglandin H2 + A + H2O
  2. N(6),N(6)-dimethyl-L-lysyl(4)-[histone H3] + 2 A + 2 H2O = L-lysyl(4)-[histone H3] + 2 formaldehyde + 2 AH2
  3. sarcosine + O2 + H2O = formaldehyde + glycine + H2O2

  Catalysed by PTGS1, PTGS2, KDM1A, KDM1B and 1 moreOne of 3 routes

• (6S)-5,6,7,8-tetrahydrofolateReach from here →
  1. (5Z,8Z,11Z,14Z)-eicosatetraenoate + AH2 + 2 O2 = prostaglandin H2 + A + H2O
  2. uridine(34) in tRNA + 5,10-methylenetetrahydrofolate + taurine + GTP + A + H2O = 5-taurinomethyluridine(34) in tRNA + 7,8-dihydrofolate + GDP + AH2 + phosphate + H(+)
  3. (6S)-5,6,7,8-tetrahydrofolate + NADP(+) = 7,8-dihydrofolate + NADPH + H(+)

  Catalysed by PTGS1, PTGS2, MTO1, DHFR and 1 moreOne of 2 routes

• (13S)-hydroperoxy-(9Z,11E)-octadecadienoateReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. Linoleate:oxygen 13-oxidoreductase

  Catalysed by ALOX15B, ALOX15cytosol, extracellular space

• L-dopaReach from here →
  1. transport of arachidonate (cytosol to extracellular)
  2. transport of dopamine (cytosol to extracellular)
  3. L-dopa + H(+) = dopamine + CO2

  Catalysed by SLCO1B1, SLCO1A2, SLCO1B3, DDCextracellular space, cytosolOne of 3 routes