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

Three steps

• 1-dodecanoyl-sn-glycerol 3-phosphateReach from here →
  1. 2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-glycerol + H2O = glycerol + (5Z,8Z,11Z,14Z)-eicosatetraenoate + H(+)
  2. glycerol + ATP = sn-glycerol 3-phosphate + ADP + H(+)
  3. dodecanoyl-CoA + sn-glycerol 3-phosphate = 1-dodecanoyl-sn-glycerol 3-phosphate + CoA

  Catalysed by FAAH, CES2, ABHD16A, EPHX1 and 14 more

• 1-hexadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phospho-D-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-hexadecanoyl-sn-glycero-3-phospho-(1D-myo-inositol) + (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA = 1-hexadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phospho-D-myo-inositol + CoA

  Catalysed by FAAH, SLC27A2, ACSL4, ACSL3 and 9 morecytosol

• 1-hexadecanoyl-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-hexadecanoyl-sn-glycero-3-phosphate + (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA = 1-hexadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphate + CoA

  Catalysed by FAAH, SLC27A2, ACSL4, ACSL3 and 10 morecytosol

• 1-hexadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholineReach 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 + 1-hexadecanoyl-sn-glycero-3-phosphocholine = 1-hexadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholine + CoA

  Catalysed by FAAH, SLC27A2, ACSL4, ACSL3 and 10 morecytosol

• 1-hexadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphoethanolamineReach 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-hexadecanoyl-sn-glycero-3-phosphoethanolamine + (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA = 1-hexadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphoethanolamine + CoA

  Catalysed by FAAH, SLC27A2, ACSL4, ACSL3 and 9 morecytosol

• (7Z,10Z,13Z,16Z)-3-oxodocosatetraenoyl-CoAReach 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 + malonyl-CoA + H(+) = (7Z,10Z,13Z,16Z)-3-oxodocosatetraenoyl-CoA + CO2 + CoA

  Catalysed by FAAH, SLC27A2, ACSL4, ACSL3 and 11 morecytosol

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

• 1-(9Z-octadecenoyl)-sn-glycero-3-phosphateReach from here →
  1. 2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-glycerol + H2O = glycerol + (5Z,8Z,11Z,14Z)-eicosatetraenoate + H(+)
  2. glycerol + ATP = sn-glycerol 3-phosphate + ADP + H(+)
  3. sn-glycerol 3-phosphate + (9Z)-octadecenoyl-CoA = 1-(9Z-octadecenoyl)-sn-glycero-3-phosphate + CoA

  Catalysed by FAAH, CES2, ABHD16A, EPHX1 and 14 more

• 1-(9Z,12Z)-octadecadienoyl-sn-glycero-3-phosphateReach from here →
  1. 2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-glycerol + H2O = glycerol + (5Z,8Z,11Z,14Z)-eicosatetraenoate + H(+)
  2. glycerol + ATP = sn-glycerol 3-phosphate + ADP + H(+)
  3. (9Z,12Z)-octadecadienoyl-CoA + sn-glycerol 3-phosphate = 1-(9Z,12Z)-octadecadienoyl-sn-glycero-3-phosphate + CoA

  Catalysed by FAAH, CES2, ABHD16A, EPHX1 and 14 more

• 1-octadecanoyl-sn-glycero-3-phosphateReach from here →
  1. 2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-glycerol + H2O = glycerol + (5Z,8Z,11Z,14Z)-eicosatetraenoate + H(+)
  2. glycerol + ATP = sn-glycerol 3-phosphate + ADP + H(+)
  3. sn-glycerol 3-phosphate + octadecanoyl-CoA = 1-octadecanoyl-sn-glycero-3-phosphate + CoA

  Catalysed by FAAH, CES2, ABHD16A, EPHX1 and 13 moreOne of 2 routes

• 1-(9Z)-octadecenoyl-2-(5Z,8Z,11Z,14Z)-icosatetraenoyl-sn-glycero-3-phosphocholineReach 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-phosphocholine + (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA = 1-(9Z)-octadecenoyl-2-(5Z,8Z,11Z,14Z)-icosatetraenoyl-sn-glycero-3-phosphocholine + CoA

  Catalysed by FAAH, SLC27A2, ACSL4, ACSL3 and 11 morecytosol

• 1-(9Z-octadecenoyl)-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phospho-L-serineReach 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-L-serine + (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA = 1-(9Z-octadecenoyl)-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phospho-L-serine + CoA

  Catalysed by FAAH, SLC27A2, ACSL4, ACSL3 and 11 morecytosol

• 1-(9Z)-octadecenoyl-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-(9Z-octadecenoyl)-sn-glycero-3-phosphate + (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA = 1-(9Z)-octadecenoyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphate + CoA

  Catalysed by FAAH, SLC27A2, ACSL4, ACSL3 and 14 morecytosol

• 1-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphateReach from here →
  1. fatty acid amide hydrolase (2-arachidonoylglycerol)
  2. Arachidonate:CoA ligase (AMP-forming)
  3. glycerol-3-phosphate 1-O-acyltransferase (arachidonyl-CoA)

  Catalysed by FAAH, SLC27A2, ACSL4, ACSL3 and 9 morecytosolOne of 3 routes

• 1-octadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholineReach 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-octadecanoyl-sn-glycero-3-phosphocholine + (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA = 1-octadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholine + CoA

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

• 1-dodecanoyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphocholineReach 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-dodecanoyl-sn-glycero-3-phosphocholine + (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA = 1-dodecanoyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphocholine + CoA

  Catalysed by FAAH, SLC27A2, ACSL4, ACSL3 and 9 morecytosol

• 1-eicosanoyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphocholineReach 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-eicosanoyl-sn-glycero-3-phosphocholine + (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA = 1-eicosanoyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphocholine + CoA

  Catalysed by FAAH, SLC27A2, ACSL4, ACSL3 and 9 morecytosol

• 1-(9Z)-octadecenoyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphoethanolamineReach 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-phosphoethanolamine + (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA = 1-(9Z)-octadecenoyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphoethanolamine + CoA

  Catalysed by FAAH, SLC27A2, ACSL4, ACSL3 and 9 morecytosol

• 1-octadecanoyl-2-hexadecanoyl-sn-glycero-3-phosphocholineReach from here →
  1. 2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-glycerol + H2O = glycerol + (5Z,8Z,11Z,14Z)-eicosatetraenoate + H(+)
  2. 1-octadecanoyl-2-(9Z,12Z,15Z-octadecatrienoyl)-sn-glycero-3-phosphocholine + glycerol = 1-(9Z,12Z,15Z-octadecatrienoyl)-glycerol + 1-octadecanoyl-sn-glycero-3-phosphocholine
  3. 1-octadecanoyl-sn-glycero-3-phosphocholine + hexadecanoyl-CoA = 1-octadecanoyl-2-hexadecanoyl-sn-glycero-3-phosphocholine + CoA

  Catalysed by FAAH, CES2, ABHD16A, EPHX1 and 10 more

• 1-hexadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phospho-L-serineReach 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-hexadecanoyl-sn-glycero-3-phospho-L-serine + (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA = 1-hexadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phospho-L-serine + CoA

  Catalysed by FAAH, SLC27A2, ACSL4, ACSL3 and 9 morecytosol

• 1-octadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phosphocholineReach from here →
  1. 2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-glycerol + H2O = glycerol + (5Z,8Z,11Z,14Z)-eicosatetraenoate + H(+)
  2. 1-octadecanoyl-2-(9Z,12Z,15Z-octadecatrienoyl)-sn-glycero-3-phosphocholine + glycerol = 1-(9Z,12Z,15Z-octadecatrienoyl)-glycerol + 1-octadecanoyl-sn-glycero-3-phosphocholine
  3. 1-octadecanoyl-sn-glycero-3-phosphocholine + (9Z)-octadecenoyl-CoA = 1-octadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine + CoA

  Catalysed by FAAH, CES2, ABHD16A, EPHX1 and 9 more

• 1-acyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholineReach 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 + a 1-acyl-sn-glycero-3-phosphocholine = 1-acyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholine + CoA

  Catalysed by FAAH, SLC27A2, ACSL4, ACSL3 and 9 morecytosol

• 1-acyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phospho-L-serineReach 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. a 1-acyl-sn-glycero-3-phospho-L-serine + (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA = 1-acyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phospho-L-serine + CoA

  Catalysed by FAAH, SLC27A2, ACSL4, ACSL3 and 9 morecytosol

• 1-acyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphoethanolamineReach 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. a 1-acyl-sn-glycero-3-phosphoethanolamine + (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA = 1-acyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphoethanolamine + CoA

  Catalysed by FAAH, SLC27A2, ACSL4, ACSL3 and 10 morecytosol

• 1-octadecanoyl-2-acetyl-sn-glycero-3-phosphocholineReach from here →
  1. 2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-glycerol + H2O = glycerol + (5Z,8Z,11Z,14Z)-eicosatetraenoate + H(+)
  2. 1-octadecanoyl-2-(9Z,12Z,15Z-octadecatrienoyl)-sn-glycero-3-phosphocholine + glycerol = 1-(9Z,12Z,15Z-octadecatrienoyl)-glycerol + 1-octadecanoyl-sn-glycero-3-phosphocholine
  3. 1-octadecanoyl-sn-glycero-3-phosphocholine + acetyl-CoA = 1-octadecanoyl-2-acetyl-sn-glycero-3-phosphocholine + CoA

  Catalysed by FAAH, CES2, ABHD16A, EPHX1 and 9 more

• 12-oxo-(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 = 12-oxo-(5Z,8Z,10E,14Z)-eicosatetraenoate + H2O

  Catalysed by FAAH, ALOX5, ALOX15, ALOX12 and 5 morecytosolOne of 2 routes

• (8R)-hydroxy-(11R,12R)-epoxy-(5Z,9E,14Z)-eicosatrienoateReach from here →
  1. fatty acid amide hydrolase (2-arachidonoylglycerol)
  2. (5Z,8Z,11Z,14Z)-eicosatetraenoate + O2 = (12R)-hydroperoxy-(5Z,8Z,10E,14Z)-eicosatetraenoate
  3. (12R)-hydroperoxy-(5Z,8Z,10E,14Z)-eicosatetraenoate = (8R)-hydroxy-(11R,12R)-epoxy-(5Z,9E,14Z)-eicosatrienoate

  Catalysed by FAAH, ALOX12B, ALOXE3cytosol

• (8R)-hydroxy-(11S,12S)-epoxy-(5Z,9E,14Z)-eicosatrienoateReach 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 = (8R)-hydroxy-(11S,12S)-epoxy-(5Z,9E,14Z)-eicosatrienoate

  Catalysed by FAAH, ALOX5, ALOX15, ALOX12 and 1 morecytosol

• (10R)-hydroxy-(11S,12S)-epoxy-(5Z,8Z,14Z)-eicosatrienoateReach 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 = (10R)-hydroxy-(11S,12S)-epoxy-(5Z,8Z,14Z)-eicosatrienoate

  Catalysed by FAAH, ALOX5, ALOX15, ALOX12 and 1 morecytosol

• (13R)-hydroxy-(14S,15S)-epoxy-(5Z,8Z,11Z)-eicosatrienoateReach from here →
  1. fatty acid amide hydrolase (2-arachidonoylglycerol)
  2. (5Z,8Z,11Z,14Z)-eicosatetraenoate + O2 = (15S)-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoate
  3. (15S)-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoate = (13R)-hydroxy-(14S,15S)-epoxy-(5Z,8Z,11Z)-eicosatrienoate

  Catalysed by FAAH, ALOX15B, ALOX15, ALOX12 and 2 morecytosol

• a 1-acyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phospho-(1D-myo-inositol)Reach 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. a 1-acyl-sn-glycero-3-phospho-(1D-myo-inositol) + (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA = a 1-acyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phospho-(1D-myo-inositol) + CoA

  Catalysed by FAAH, SLC27A2, ACSL4, ACSL3 and 10 morecytosol

• 1-O-octadecyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphocholineReach 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-octadecyl-sn-glycero-3-phosphocholine + (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA = 1-O-octadecyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphocholine + CoA

  Catalysed by FAAH, SLC27A2, ACSL4, ACSL3 and 9 morecytosol

• 1-octadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phospho-(1'-sn-glycerol)Reach 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-octadecanoyl-sn-glycero-3-phospho-(1'-sn-glycerol) + (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA = 1-octadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phospho-(1'-sn-glycerol) + CoA

  Catalysed by FAAH, SLC27A2, ACSL4, ACSL3 and 9 morecytosol

• 1-(9Z,12Z,15Z-octadecatrienoyl)-2-(9Z-octadecenoyl)-glycerolReach from here →
  1. 2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-glycerol + H2O = glycerol + (5Z,8Z,11Z,14Z)-eicosatetraenoate + H(+)
  2. 1-octadecanoyl-2-(9Z,12Z,15Z-octadecatrienoyl)-sn-glycero-3-phosphocholine + glycerol = 1-(9Z,12Z,15Z-octadecatrienoyl)-glycerol + 1-octadecanoyl-sn-glycero-3-phosphocholine
  3. 1-(9Z,12Z,15Z-octadecatrienoyl)-glycerol + (9Z)-octadecenoyl-CoA = 1-(9Z,12Z,15Z-octadecatrienoyl)-2-(9Z-octadecenoyl)-glycerol + CoA

  Catalysed by FAAH, CES2, ABHD16A, EPHX1 and 10 more

• 1-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-2-(9Z-octadecenoyl)-glycerolReach 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. 2-(9Z-octadecenoyl)-glycerol + (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA = 1-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-2-(9Z-octadecenoyl)-glycerol + CoA

  Catalysed by FAAH, SLC27A2, ACSL4, ACSL3 and 10 morecytosolOne of 2 routes

• 1'-[1,2-diacyl-sn-glycero-3-phospho],3'-[1-acyl,2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phospho]-glycerolReach 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'-[1,2-diacyl-sn-glycero-3-phospho],3'-[1-acyl-sn-glycero-3-phospho]-glycerol + (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA = 1'-[1,2-diacyl-sn-glycero-3-phospho],3'-[1-acyl,2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phospho]-glycerol + CoA

  Catalysed by FAAH, SLC27A2, ACSL4, ACSL3 and 9 morecytosol

• 1'-[1-acyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phospho],3'-[1-acyl,2-hydroxy-sn-glycero-3-phospho]-glycerolReach 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',3'-bis-[1-acyl-sn-glycero-3-phospho]-glycerol + (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA = 1'-[1-acyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phospho],3'-[1-acyl,2-hydroxy-sn-glycero-3-phospho]-glycerol + CoA

  Catalysed by FAAH, SLC27A2, ACSL4, ACSL3 and 9 morecytosol

• 2-[(5Z,8Z,11Z,14Z)-eicosatetraenoylamino]ethyl (9Z)-octadecenoateReach from here →
  1. fatty acid amide hydrolase (2-arachidonoylglycerol)
  2. fatty acylamide amidohydrolase
  3. N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-ethanolamine + 1,2-di-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine = 2-[(5Z,8Z,11Z,14Z)-eicosatetraenoylamino]ethyl (9Z)-octadecenoate + (9Z-octadecenoyl)-sn-glycero-3-phosphocholine

  Catalysed by FAAH, PLA2G15cytosol

• (9Z-octadecenoyl)-sn-glycero-3-phosphocholineReach from here →
  1. fatty acid amide hydrolase (2-arachidonoylglycerol)
  2. fatty acylamide amidohydrolase
  3. N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-ethanolamine + 1,2-di-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine = 2-[(5Z,8Z,11Z,14Z)-eicosatetraenoylamino]ethyl (9Z)-octadecenoate + (9Z-octadecenoyl)-sn-glycero-3-phosphocholine

  Catalysed by FAAH, PLA2G15cytosol

• 20-oxo-(5Z,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. fatty acid amide hydrolase (2-arachidonoylglycerol)
  2. arachidonic acid:oxygen 1-oxidoreductase
  3. 10-HETE[n] + NAD+[n] = H+[n] + NADH[n] + 20-oxo-(5Z,8Z,11Z,14Z)-eicosatetraenoate[n]

  Catalysed by FAAH, CYP1A1, CYP1A2, CYP2E1 and 25 morecytosol, nucleusOne of 3 routes

• O-dodecanoyl-R-carnitineReach from here →
  1. fatty acid amide hydrolase (2-arachidonoylglycerol)
  2. Utilized Transport
  3. carnitine O-palmitoyltransferase (dodecanoylcarnitine)

  Catalysed by FAAH, CPT1A, CPT1C, CPT1Bcytosol, endoplasmic reticulumOne of 7 routes

• 1-octadecanoyl-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-octadecanoyl-sn-glycero-3-phosphate + (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA = 1-octadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphate + CoA

  Catalysed by FAAH, SLC27A2, ACSL4, ACSL3 and 9 morecytosol

• (11Z,14Z)-eicosadienoateReach 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

• (17Z)-hexacosenoateReach 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

• (7Z,10Z,13Z,16Z,19Z)-docosapentaenoateReach 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

• (7Z,10Z,13Z,16Z)-docosatetraenoateReach 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

• 1-O-(1Z)-alkenyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphoethanolamineReach 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. a 1-O-(1Z-alkenyl)-sn-glycero-3-phosphoethanolamine + (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA = 1-O-(1Z)-alkenyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphoethanolamine + CoA

  Catalysed by FAAH, SLC27A2, ACSL4, ACSL3 and 10 morecytosol

• 7R-hydroxy-5S,6S-epoxy-(8Z,11Z,14Z)-eicosatrienoateReach 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 = 7R-hydroxy-5S,6S-epoxy-(8Z,11Z,14Z)-eicosatrienoate

  Catalysed by FAAH, ALOX5, ALOXE3cytosol

• (5Z,8Z,11Z)-eicosatrienoateReach 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

• ursodeoxycholateReach 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, SLCO1B1, SLCO1A2, SLCO1B3cytosol, extracellular spaceOne of 4 routes