2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-glycerol

Three steps

• 1-(9Z-octadecenoyl)-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phospho-1D-myo-inositolReach from here →
  1. fatty acid amide hydrolase (2-arachidonoylglycerol)
  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 FAAH, SLC27A2, ACSL4, ACSL3 and 10 morecytosol

• 1-heptadecanoyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphateReach from here →
  1. fatty acid amide hydrolase (2-arachidonoylglycerol)
  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 FAAH, SLC27A2, ACSL4, ACSL3 and 9 morecytosol

• tricosanoateReach from here →
  1. fatty acid amide hydrolase (2-arachidonoylglycerol)
  2. (10Z)-heptadecenoic acid formation
  3. (10Z)-heptadecenoic acid formation

  Catalysed by FAAHcytosol, extracellular spaceOne of 12 routes

• cholesteryl (5Z,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. fatty acid amide hydrolase (2-arachidonoylglycerol)
  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 FAAH, SLC27A2, ACSL4, ACSL3 and 10 morecytosol

• 1-heptadecanoyl-sn-glycero-3-phosphoserineReach from here →
  1. fatty acid amide hydrolase (2-arachidonoylglycerol)
  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 FAAH, ABHD16Acytosol

• 1-heptadecanoyl-sn-glycero-3-phosphoethanolamineReach from here →
  1. fatty acid amide hydrolase (2-arachidonoylglycerol)
  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 FAAH, ABHD16Acytosol

• O-4,8-dimethylnonanoyl-(R)-carnitineReach from here →
  1. fatty acid amide hydrolase (2-arachidonoylglycerol)
  2. Utilized Transport
  3. Carnitine Dimethyl Nonanoyl Transferase, Revsible, Peroxisomal

  Catalysed by FAAH, CRAT, CROTcytosol, endoplasmic reticulum, peroxisomeOne of 5 routes

• 1-O-(9Z-octadecenyl)-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphateReach from here →
  1. fatty acid amide hydrolase (2-arachidonoylglycerol)
  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 FAAH, SLC27A2, ACSL4, ACSL3 and 9 morecytosol

• (5S)-hydroxy-(6E,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. fatty acid amide hydrolase (2-arachidonoylglycerol)
  2. (5Z,8Z,11Z,14Z)-eicosatetraenoate + O2 = (5S)-hydroperoxy-(6E,8Z,11Z,14Z)-eicosatetraenoate
  3. (5S)-hydroperoxy-(6E,8Z,11Z,14Z)-eicosatetraenoate + 2 glutathione = (5S)-hydroxy-(6E,8Z,11Z,14Z)-eicosatetraenoate + glutathione disulfide + H2O

  Catalysed by FAAH, ALOX5, PTGES, MGST3 and 4 morecytosol

• (12S)-hydroxy-(5Z,8Z,10E,14Z)-eicosatetraenoateReach from here →
  1. fatty acid amide hydrolase (2-arachidonoylglycerol)
  2. (5Z,8Z,11Z,14Z)-eicosatetraenoate + O2 = (12S)-hydroperoxy-(5Z,8Z,10E,14Z)-eicosatetraenoate
  3. (12S)-hydroperoxy-(5Z,8Z,10E,14Z)-eicosatetraenoate + 2 glutathione = (12S)-hydroxy-(5Z,8Z,10E,14Z)-eicosatetraenoate + glutathione disulfide + H2O

  Catalysed by FAAH, ALOX5, ALOX15, ALOX12 and 2 morecytosol

• (12S)-hydroxy-(5Z,8E,10E)-heptadecatrienoateReach from here →
  1. fatty acid amide hydrolase (2-arachidonoylglycerol)
  2. prostaglandin-endoperoxide synthase (arachidonate)
  3. prostaglandin H2 = (12S)-hydroxy-(5Z,8E,10E)-heptadecatrienoate + malonaldehyde

  Catalysed by FAAH, PTGS1, PTGS2, TBXAS1 and 2 morecytosol

• thromboxane B2Reach from here →
  1. fatty acid amide hydrolase (2-arachidonoylglycerol)
  2. transport of arachidonate (cytosol to extracellular)
  3. transport of S-glutathionyl-2-4-dinitrobenzene (cytosol to extracellular)

  Catalysed by FAAH, SLCO1B1cytosol, extracellular spaceOne of 4 routes

• 11-oxo-(5Z,8Z,12E,14Z)-eicosatetraenoateReach from here →
  1. fatty acid amide hydrolase (2-arachidonoylglycerol)
  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 FAAH, PTGS2, HPGDcytosol

• 19-hydroxyprostaglandin H2Reach from here →
  1. fatty acid amide hydrolase (2-arachidonoylglycerol)
  2. prostaglandin-endoperoxide synthase (arachidonate)
  3. prostaglandin H2 + reduced [NADPH--hemoprotein reductase] + O2 = 19-hydroxyprostaglandin H2 + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by FAAH, PTGS1, PTGS2, CYP4F8cytosol

• taurochenodeoxycholateReach from here →
  1. fatty acid amide hydrolase (2-arachidonoylglycerol)
  2. transport of arachidonate (cytosol to extracellular)
  3. solute carrier organic anion transporter (S-glutathionyl-2-4-dinitrobenzene)

  Catalysed by FAAH, SLCO1B1, SLCO1A2, SLC7A9 and 1 morecytosol, extracellular spaceOne of 4 routes