(11S,15S)-dihydroxy-14(R)-S-glutathionyl-(5Z,8Z,12E)-eicosatrienoate

Three steps

• (12R)-hydroperoxy-(5Z,8Z,10E,14Z)-eicosatetraenoateReach from here →
  1. glutathione transferase (GSH)
  2. transport of arachidonate and GSH (cytosol to extracellular)
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + O2 = (12R)-hydroperoxy-(5Z,8Z,10E,14Z)-eicosatetraenoate

  Catalysed by PTGES, MGST3, GSTA4, GSTZ1 and 18 morecytosol, extracellular space

• (8S)-hydroperoxy-(5Z,9E,11Z,14Z)-eicosatetraenoateReach from here →
  1. glutathione transferase (GSH)
  2. transport of arachidonate and GSH (cytosol to extracellular)
  3. Arachidonate:oxygen 8-oxidoreductase

  Catalysed by PTGES, MGST3, GSTA4, GSTZ1 and 18 morecytosol, extracellular spaceOne of 2 routes

• 2-O-(5Z,8Z,11Z,14Z)-eicosatetraenylglycerolReach from here →
  1. glutathione transferase (GSH)
  2. transport of arachidonate and GSH (cytosol to extracellular)
  3. fatty acid amide hydrolase (arachidonate)

  Catalysed by PTGES, MGST3, GSTA4, GSTZ1 and 18 morecytosol, extracellular space

• 11,12-epoxy-(5Z,8Z,14Z)-eicosatrienoateReach from here →
  1. glutathione transferase (GSH)
  2. transport of arachidonate and GSH (cytosol to extracellular)
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + reduced [NADPH--hemoprotein reductase] + O2 = 11,12-epoxy-(5Z,8Z,14Z)-eicosatrienoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by PTGES, MGST3, GSTA4, GSTZ1 and 18 morecytosol, extracellular space

• 19-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. glutathione transferase (GSH)
  2. transport of arachidonate and GSH (cytosol to extracellular)
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + reduced [NADPH--hemoprotein reductase] + O2 = 19-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by PTGES, MGST3, GSTA4, GSTZ1 and 22 morecytosol, extracellular space

• 20-oxo-(5Z,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. glutathione transferase (GSH)
  2. Resistance-Nodulation-Cell Division (Rnd) Tcdb:2.A.60.1.2
  3. 10-HETE[n] + NAD+[n] = H+[n] + NADH[n] + 20-oxo-(5Z,8Z,11Z,14Z)-eicosatetraenoate[n]

  Catalysed by PTGES, MGST3, GSTA4, GSTZ1 and 19 morecytosol, extracellular space, nucleusOne of 3 routes

• 7-oxolithocholateReach from here →
  1. glutathione transferase (GSH)
  2. transport of GSH and ursodeoxycholate (cytosol to extracellular)
  3. ursodeoxycholate + NAD(+) = 7-oxolithocholate + NADH + H(+)

  Catalysed by PTGES, MGST3, GSTA4, GSTZ1 and 20 morecytosol, extracellular space

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

  Catalysed by PTGES, MGST3, GSTA4, GSTZ1 and 18 morecytosol, extracellular spaceOne of 2 routes

• (15R)-hydroxy-(5Z,8Z,11Z,13E)-eicosatetraenoateReach from here →
  1. glutathione transferase (GSH)
  2. transport of arachidonate and GSH (cytosol to extracellular)
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + AH2 + O2 = (15R)-hydroxy-(5Z,8Z,11Z,13E)-eicosatetraenoate + A + H2O

  Catalysed by PTGES, MGST3, GSTA4, GSTZ1 and 18 morecytosol, extracellular spaceOne of 2 routes

• (15R)-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoateReach from here →
  1. glutathione transferase (GSH)
  2. transport of arachidonate and GSH (cytosol to extracellular)
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + O2 = (15R)-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoate

  Catalysed by PTGES, MGST3, GSTA4, GSTZ1 and 18 morecytosol, extracellular space

• 11R-hydroperoxy-(5Z,8Z,12E,14Z)-eicosatetraenoateReach from here →
  1. glutathione transferase (GSH)
  2. transport of arachidonate and GSH (cytosol to extracellular)
  3. Arachidonate: oxygen 11-oxidoreductase

  Catalysed by PTGES, MGST3, GSTA4, GSTZ1 and 18 morecytosol, extracellular spaceOne of 2 routes

• thio-Mo-molybdopterinReach from here →
  1. glutathione transferase (GSH)
  2. cystine to cysteine conversion
  3. Mo-molybdopterin + L-cysteine + AH2 = thio-Mo-molybdopterin + L-alanine + A + H2O

  Catalysed by PTGES, MGST3, GSTA4, GSTZ1 and 18 morecytosol

• (12R)-hydroxy-(5Z,8Z,10E,14Z)-eicosatetraenoateReach from here →
  1. glutathione transferase (GSH)
  2. transport of arachidonate and GSH (cytosol to extracellular)
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + reduced [NADPH--hemoprotein reductase] + O2 = (12R)-hydroxy-(5Z,8Z,10E,14Z)-eicosatetraenoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by PTGES, MGST3, GSTA4, GSTZ1 and 18 morecytosol, extracellular space

• 14,15-epoxy-(5Z,8Z,11Z)-eicosatrienoateReach from here →
  1. glutathione transferase (GSH)
  2. transport of arachidonate and GSH (cytosol to extracellular)
  3. unspecific monooxygenase (arachidonate)

  Catalysed by PTGES, MGST3, GSTA4, GSTZ1 and 44 morecytosol, extracellular spaceOne of 4 routes

• 8,9-epoxy-(5Z,11Z,14Z)-eicosatrienoateReach from here →
  1. glutathione transferase (GSH)
  2. transport of arachidonate and GSH (cytosol to extracellular)
  3. unspecific monooxygenase (arachidonate)

  Catalysed by PTGES, MGST3, GSTA4, GSTZ1 and 43 morecytosol, extracellular spaceOne of 3 routes

• 1-heptadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphoserineReach from here →
  1. glutathione transferase (GSH)
  2. transport of arachidonate and GSH (cytosol to extracellular)
  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 PTGES, MGST3, GSTA4, GSTZ1 and 18 morecytosol, extracellular space

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

  Catalysed by PTGES, MGST3, GSTA4, GSTZ1 and 18 morecytosol, extracellular space

• 1-heptadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphoethanolamineReach from here →
  1. glutathione transferase (GSH)
  2. transport of arachidonate and GSH (cytosol to extracellular)
  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 PTGES, MGST3, GSTA4, GSTZ1 and 18 morecytosol, extracellular space

• 11beta-prostaglandin F2Reach from here →
  1. glutathione transferase (GSH)
  2. transport of GSH and prostaglandin D2 (cytosol to extracellular)
  3. prostaglandin D2 + NADPH + H(+) = 11beta-prostaglandin F2 + NADP(+)

  Catalysed by PTGES, MGST3, GSTA4, GSTZ1 and 20 morecytosol, extracellular space

• (12S)-hydroxy-(5Z,8E,10E)-heptadecatrienoateReach from here →
  1. glutathione transferase (GSH)
  2. transport of GSH and prostaglandin H2 (cytosol to extracellular)
  3. prostaglandin H2 = (12S)-hydroxy-(5Z,8E,10E)-heptadecatrienoate + malonaldehyde

  Catalysed by PTGES, MGST3, GSTA4, GSTZ1 and 21 morecytosol, extracellular space

• (18R)-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. glutathione transferase (GSH)
  2. transport of arachidonate and GSH (cytosol to extracellular)
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + reduced [NADPH--hemoprotein reductase] + O2 = (18R)-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by PTGES, MGST3, GSTA4, GSTZ1 and 18 morecytosol, extracellular space

• prostaglandin H1Reach from here →
  1. glutathione transferase (GSH)
  2. transport of GSH and prostaglandin E1 (cytosol to extracellular)
  3. prostaglandin-E synthase (prostaglandin E1)

  Catalysed by PTGES, MGST3, GSTA4, GSTZ1 and 20 morecytosol, extracellular spaceOne of 2 routes

• 19-hydroxyprostaglandin H2Reach from here →
  1. glutathione transferase (GSH)
  2. transport of GSH and prostaglandin H2 (cytosol to extracellular)
  3. prostaglandin H2 + reduced [NADPH--hemoprotein reductase] + O2 = 19-hydroxyprostaglandin H2 + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by PTGES, MGST3, GSTA4, GSTZ1 and 19 morecytosol, extracellular space

• 15-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoateReach from here →
  1. glutathione transferase (GSH)
  2. transport of arachidonate and GSH (cytosol to extracellular)
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + O2 = 15-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoate

  Catalysed by PTGES, MGST3, GSTA4, GSTZ1 and 18 morecytosol, extracellular space

• 5-hydroperoxy-(6E,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. glutathione transferase (GSH)
  2. transport of arachidonate and GSH (cytosol to extracellular)
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + O2 = 5-hydroperoxy-(6E,8Z,11Z,14Z)-eicosatetraenoate

  Catalysed by PTGES, MGST3, GSTA4, GSTZ1 and 18 morecytosol, extracellular space