CHEBI:16856

Three steps

• 1-(9Z-octadecenoyl)-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phospho-1D-myo-inositolReach from here →
  1. transport of arachidonate and GSH (cytosol to extracellular)
  2. (5Z,8Z,11Z,14Z)-eicosatetraenoate + ATP + CoA = (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA + AMP + diphosphate
  3. 1-(9Z-octadecenoyl)-sn-glycero-3-phospho-(1D-myo-inositol) + (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA = 1-(9Z-octadecenoyl)-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phospho-1D-myo-inositol + CoA

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 9 moreextracellular space, cytosol

• 1-heptadecanoyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphateReach from here →
  1. transport of arachidonate and GSH (cytosol to extracellular)
  2. (5Z,8Z,11Z,14Z)-eicosatetraenoate + ATP + CoA = (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA + AMP + diphosphate
  3. 1-heptadecanoyl-sn-glycero-3-phosphate + (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA = 1-heptadecanoyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphate + CoA

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 8 moreextracellular space, cytosol

• tricosanoateReach from here →
  1. transport of arachidonate and GSH (cytosol to extracellular)
  2. (10Z)-heptadecenoic acid formation
  3. (10Z)-heptadecenoic acid formation

  No catalyst recordedextracellular space, cytosolOne of 12 routes

• cholesteryl (5Z,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. transport of arachidonate and GSH (cytosol to extracellular)
  2. (5Z,8Z,11Z,14Z)-eicosatetraenoate + ATP + CoA = (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA + AMP + diphosphate
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA + cholesterol = cholesteryl (5Z,8Z,11Z,14Z)-eicosatetraenoate + CoA

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 9 moreextracellular space, cytosol

• 17beta-estradiol 17-O-(beta-D-glucuronate)Reach from here →
  1. solute carrier organic anion transporter (glycocholate)
  2. glycocholate(out) + glutarate(in) = glycocholate(in) + glutarate(out)
  3. 17beta-estradiol 17-O-(beta-D-glucuronate)(out) + glutarate(in) = 17beta-estradiol 17-O-(beta-D-glucuronate)(in) + glutarate(out)

  Catalysed by SLCO1A2, SLCO1B3, SLC22A24extracellular space, cytosol, inner side of the membrane, outer side of the membraneOne of 2 routes

• glycodeoxycholateReach from here →
  1. Glutathione: 5-HPETE oxidoreductase
  2. 2 glutathione + NADP(+) = glutathione disulfide + NADPH + H(+)
  3. glycodeoxycholate(in) + glutathione(in) + ATP + H2O = glycodeoxycholate(out) + glutathione(out) + ADP + phosphate + H(+)

  Catalysed by GPX5, GPX1, GPX2, GPX3 and 7 morecytosol, inner side of the membrane, outer side of the membraneOne of 4 routes

• (R)-lipoateReach from here →
  1. transport of dopamine and GSH (cytosol to extracellular)
  2. dopamine,ascorbate:oxygen oxidoreductase (beta-hydroxylating)
  3. ascorbate to dehydroascorbic acid conversion

  Catalysed by SLCO1A2, SLCO1B3, DBHextracellular space, cytosol

• 1-heptadecanoyl-sn-glycero-3-phosphoserineReach from here →
  1. transport of arachidonate and GSH (cytosol to extracellular)
  2. 1-heptadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphoserine + H2O = 1-heptadecanoyl-sn-glycero-3-phosphoserine + (5Z,8Z,11Z,14Z)-eicosatetraenoate + H(+)
  3. 1-heptadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphoserine + H2O = 1-heptadecanoyl-sn-glycero-3-phosphoserine + (5Z,8Z,11Z,14Z)-eicosatetraenoate + H(+)

  Catalysed by ABHD16Aextracellular space, cytosol

• 1-heptadecanoyl-sn-glycero-3-phosphoethanolamineReach from here →
  1. transport of arachidonate and GSH (cytosol to extracellular)
  2. 1-heptadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphoethanolamine + H2O = 1-heptadecanoyl-sn-glycero-3-phosphoethanolamine + (5Z,8Z,11Z,14Z)-eicosatetraenoate + H(+)
  3. 1-heptadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphoethanolamine + H2O = 1-heptadecanoyl-sn-glycero-3-phosphoethanolamine + (5Z,8Z,11Z,14Z)-eicosatetraenoate + H(+)

  Catalysed by ABHD16Aextracellular space, cytosol

• (5Z)-tetradecenoyl-CoAReach from here →
  1. transport of GSH and leukotriene E4 (cytosol to extracellular)
  2. N-acetyl-LTE4 to leukotriene E4 conversion
  3. long-chain-fatty-acid-CoA ligase (physeteric acid)

  Catalysed by SLCO1B1, ZDHHC11B, NAA10, ESCO2 and 37 moreextracellular space, cytosolOne of 8 routes

• O-4,8-dimethylnonanoyl-(R)-carnitineReach from here →
  1. transport of arachidonate and GSH (cytosol to extracellular)
  2. Utilized Transport
  3. Carnitine Dimethyl Nonanoyl Transferase, Revsible, Peroxisomal

  Catalysed by CRAT, CROTextracellular space, cytosol, endoplasmic reticulum, peroxisomeOne of 5 routes

• (3E)-decenoyl-CoAReach from here →
  1. transport of GSH and leukotriene E4 (cytosol to extracellular)
  2. N-acetyl-LTE4 to leukotriene E4 conversion
  3. Fatty Acid Beta Oxidation (C12:1->C10:1), Mitochondrial

  Catalysed by SLCO1B1, ZDHHC11B, NAA10, ESCO2 and 33 moreextracellular space, cytosol, mitochondrial matrix

• 2-glyceryl-prostaglandin G2Reach from here →
  1. transport of arachidonate and GSH (cytosol to extracellular)
  2. fatty acid amide hydrolase (2-arachidonoylglycerol)
  3. 2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-glycerol + 2 O2 = 2-glyceryl-prostaglandin G2

  Catalysed by FAAH, PTGS2extracellular space, cytosol

• 1-O-(9Z-octadecenyl)-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphateReach from here →
  1. transport of arachidonate and GSH (cytosol to extracellular)
  2. (5Z,8Z,11Z,14Z)-eicosatetraenoate + ATP + CoA = (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA + AMP + diphosphate
  3. 1-O-(9Z-octadecenyl)-sn-glycero-3-phosphate + (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA = 1-O-(9Z-octadecenyl)-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphate + CoA

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 8 moreextracellular space, cytosol

• N-tetradecanoylglycineReach from here →
  1. leukotriene C4 synthase (GSH)
  2. leukotriene C4 hydrolysis
  3. tetradecanoyl-CoA + glycine = N-tetradecanoylglycine + CoA + H(+)

  Catalysed by LTC4S, GLYATL2cytosolOne of 2 routes

• (2R,6)-dimethylheptanoyl-CoAReach from here →
  1. transport of GSH and leukotriene E4 (cytosol to extracellular)
  2. N-acetyl-LTE4 to leukotriene E4 conversion
  3. acetyl-CoA C-acyltransferase (3-oxo-4(R),8-dimethyl-nonanoyl-CoA)

  Catalysed by SLCO1B1, ZDHHC11B, NAA10, ESCO2 and 32 moreextracellular space, cytosol, mitochondrial matrix

• N-eicosanoylglycinateReach from here →
  1. leukotriene C4 synthase (GSH)
  2. leukotriene C4 hydrolysis
  3. eicosanoyl-CoA + glycine = N-eicosanoylglycinate + CoA + H(+)

  Catalysed by LTC4S, BAATcytosol

• N-docosanoylglycineReach from here →
  1. leukotriene C4 synthase (GSH)
  2. leukotriene C4 hydrolysis
  3. docosanoyl-CoA + glycine = N-docosanoylglycine + CoA + H(+)

  Catalysed by LTC4S, BAATcytosol

• N-hexacosanoylglycineReach from here →
  1. leukotriene C4 synthase (GSH)
  2. leukotriene C4 hydrolysis
  3. hexacosanoyl-CoA + glycine = N-hexacosanoylglycine + CoA + H(+)

  Catalysed by LTC4S, BAATcytosol

• an N(2)-acyl-L-glutamineReach from here →
  1. cystine to cysteine conversion
  2. transport of cysteine and glutamine (cytosol to extracellular)
  3. an acyl-CoA + L-glutamine = an N(2)-acyl-L-glutamine + CoA + H(+)

  Catalysed by SLC3A2, SLC7A5, SLC7A10, GLYATL1B and 1 morecytosol, extracellular space

• (7Z)-hexadecenoyl-CoAReach from here →
  1. transport of GSH and leukotriene E4 (cytosol to extracellular)
  2. N-acetyl-LTE4 to leukotriene E4 conversion
  3. long-chain-fatty-acid-CoA ligase (7-palmitoleic acid)

  Catalysed by SLCO1B1, ZDHHC11B, NAA10, ESCO2 and 37 moreextracellular space, cytosolOne of 8 routes

• tricosanoyl-CoAReach from here →
  1. transport of GSH and leukotriene E4 (cytosol to extracellular)
  2. N-acetyl-LTE4 to leukotriene E4 conversion
  3. long-chain-fatty-acid-CoA ligase (tricosanoic acid)

  Catalysed by SLCO1B1, ZDHHC11B, NAA10, ESCO2 and 37 moreextracellular space, cytosolOne of 4 routes

• (5S)-hydroxy-(6E,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. Glutathione: 5-HPETE oxidoreductase
  2. 2 glutathione + NADP(+) = glutathione disulfide + NADPH + H(+)
  3. (5S)-hydroperoxy-(6E,8Z,11Z,14Z)-eicosatetraenoate + 2 glutathione = (5S)-hydroxy-(6E,8Z,11Z,14Z)-eicosatetraenoate + glutathione disulfide + H2O

  Catalysed by GPX5, GPX1, GPX2, GPX3 and 9 morecytosolOne of 2 routes

• (12S)-hydroxy-(5Z,8Z,10E,14Z)-eicosatetraenoateReach from here →
  1. Glutathione: 5-HPETE oxidoreductase
  2. 2 glutathione + NADP(+) = glutathione disulfide + NADPH + H(+)
  3. (12S)-hydroperoxy-(5Z,8Z,10E,14Z)-eicosatetraenoate + 2 glutathione = (12S)-hydroxy-(5Z,8Z,10E,14Z)-eicosatetraenoate + glutathione disulfide + H2O

  Catalysed by GPX5, GPX1, GPX2, GPX3 and 6 morecytosolOne of 2 routes

• 11-oxo-(5Z,8Z,12E,14Z)-eicosatetraenoateReach from here →
  1. transport of arachidonate and GSH (cytosol to extracellular)
  2. (5Z,8Z,11Z,14Z)-eicosatetraenoate + AH2 + O2 = (11R)-hydroxy-(5Z,8Z,12E,14Z)-eicosatetraenoate + A + H2O
  3. (11R)-hydroxy-(5Z,8Z,12E,14Z)-eicosatetraenoate + NAD(+) = 11-oxo-(5Z,8Z,12E,14Z)-eicosatetraenoate + NADH + H(+)

  Catalysed by PTGS2, HPGDextracellular space, cytosol

• an S-substituted glutathioneReach from here →
  1. Glutathione: 5-HPETE oxidoreductase
  2. 2 glutathione + NADP(+) = glutathione disulfide + NADPH + H(+)
  3. RX + glutathione = an S-substituted glutathione + a halide anion + H(+)

  Catalysed by GPX5, GPX1, GPX2, GPX3 and 29 morecytosolOne of 2 routes

• 19-hydroxyprostaglandin H1Reach from here →
  1. transport of GSH and prostaglandin E1 (cytosol to extracellular)
  2. prostaglandin-E synthase (prostaglandin E1)
  3. prostaglandin H1 + reduced [NADPH--hemoprotein reductase] + O2 = 19-hydroxyprostaglandin H1 + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by SLCO2A1, PTGES, PTGES3, PTGES2 and 1 moreextracellular space, cytosol

• (13S)-hydroxy-(9Z,11E)-octadecadienoateReach from here →
  1. Glutathione: 5-HPETE oxidoreductase
  2. 2 glutathione + NADP(+) = glutathione disulfide + NADPH + H(+)
  3. (13S)-hydroperoxy-(9Z,11E)-octadecadienoate + 2 glutathione = (13S)-hydroxy-(9Z,11E)-octadecadienoate + glutathione disulfide + H2O

  Catalysed by GPX5, GPX1, GPX2, GPX3 and 7 morecytosol

• 2-(1-hydroxyethyl)thiamine diphosphateReach from here →
  1. cystine to cysteine conversion
  2. L-cysteine hydrogen-sulfide-lyase (deaminating
  3. pyruvate:thiamin diphosphate acetaldehydetransferase (decarboxylating)

  Catalysed by CTH, PDHA1, PDHB, PDHA2cytosol, mitochondrial matrix