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

Three steps

• 1-O-(1Z)-alkenyl-2-octadecanoyl-sn-glycero-3-phosphoethanolamineReach from here →
  1. 1-octadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycerol + H2O = 2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-glycerol + octadecanoate + H(+)
  2. long-chain-fatty-acid-CoA ligase (stearate)
  3. a 1-O-(1Z-alkenyl)-sn-glycero-3-phosphoethanolamine + octadecanoyl-CoA = 1-O-(1Z)-alkenyl-2-octadecanoyl-sn-glycero-3-phosphoethanolamine + CoA

  Catalysed by DAGLB, ABHD11, DAGLA, SLC27A2 and 7 morecytosol

• (5Z,8Z,11Z)-eicosatrienoateReach from here →
  1. 1-octadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycerol + H2O = 2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-glycerol + octadecanoate + H(+)
  2. (10Z)-heptadecenoic acid formation
  3. (10Z)-heptadecenoic acid formation

  Catalysed by DAGLB, ABHD11, DAGLAcytosol, extracellular spaceOne of 12 routes

• 1-(1Z-octadecenyl)-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phospho-L-serineReach from here →
  1. 1-octadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycerol + CDP-choline = 1-octadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholine + CMP + H(+)
  2. 1-(1Z-octadecenyl)-sn-glycero-3-phosphoethanolamine + 1-octadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholine = 1-(1Z-octadecenyl)-2-(5Z,8Z,11Z,14Z- eicosatetraenoyl)-sn-glycero-3-phosphoethanolamine + 1-octadecanoyl-sn-glycero-3-phosphocholine
  3. 1-(1Z-octadecenyl)-2-(5Z,8Z,11Z,14Z- eicosatetraenoyl)-sn-glycero-3-phosphoethanolamine + L-serine = 1-(1Z-octadecenyl)-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phospho-L-serine + ethanolamine

  Catalysed by CHPT1, TMEM164, PTDSS2

• (11R)-hydroxy-(5Z,8Z,12E,14Z)-eicosatetraenoateReach from here →
  1. 1-octadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycerol + H2O = 2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-glycerol + octadecanoate + H(+)
  2. fatty acid amide hydrolase (2-arachidonoylglycerol)
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + AH2 + O2 = (11R)-hydroxy-(5Z,8Z,12E,14Z)-eicosatetraenoate + A + H2O

  Catalysed by DAGLB, ABHD11, DAGLA, FAAH and 1 morecytosolOne of 2 routes

• (15R)-hydroxy-(5Z,8Z,11Z,13E)-eicosatetraenoateReach from here →
  1. 1-octadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycerol + H2O = 2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-glycerol + octadecanoate + H(+)
  2. fatty acid amide hydrolase (2-arachidonoylglycerol)
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + AH2 + O2 = (15R)-hydroxy-(5Z,8Z,11Z,13E)-eicosatetraenoate + A + H2O

  Catalysed by DAGLB, ABHD11, DAGLA, FAAH and 1 morecytosolOne of 2 routes

• tricosanoateReach from here →
  1. 1-octadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycerol + H2O = 2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-glycerol + octadecanoate + H(+)
  2. (10Z)-heptadecenoic acid formation
  3. (10Z)-heptadecenoic acid formation

  Catalysed by DAGLB, ABHD11, DAGLAcytosol, extracellular spaceOne of 12 routes

• (15R)-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoateReach from here →
  1. 1-octadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycerol + H2O = 2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-glycerol + octadecanoate + H(+)
  2. fatty acid amide hydrolase (2-arachidonoylglycerol)
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + O2 = (15R)-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoate

  Catalysed by DAGLB, ABHD11, DAGLA, FAAH and 1 morecytosol

• 11R-hydroperoxy-(5Z,8Z,12E,14Z)-eicosatetraenoateReach from here →
  1. 1-octadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycerol + H2O = 2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-glycerol + octadecanoate + H(+)
  2. fatty acid amide hydrolase (2-arachidonoylglycerol)
  3. Arachidonate: oxygen 11-oxidoreductase

  Catalysed by DAGLB, ABHD11, DAGLA, FAAH and 1 morecytosolOne of 2 routes

• prostaglandin G2Reach from here →
  1. 1-octadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycerol + H2O = 2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-glycerol + octadecanoate + H(+)
  2. fatty acid amide hydrolase (2-arachidonoylglycerol)
  3. Arachidonate:oxygen oxidoreductase

  Catalysed by DAGLB, ABHD11, DAGLA, FAAH and 2 morecytosol, endoplasmic reticulumOne of 2 routes

• cholesteryl octadecanoateReach from here →
  1. 1-octadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycerol + H2O = 2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-glycerol + octadecanoate + H(+)
  2. long-chain-fatty-acid-CoA ligase (stearate)
  3. Acyl-CoA:cholesterol O-acyltransferase

  Catalysed by DAGLB, ABHD11, DAGLA, SLC27A2 and 8 morecytosol, endoplasmic reticulumOne of 2 routes

• N-octadecanoylhexadecasphinganineReach from here →
  1. 1-octadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycerol + H2O = 2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-glycerol + octadecanoate + H(+)
  2. long-chain-fatty-acid-CoA ligase (stearate)
  3. hexadecasphinganine + octadecanoyl-CoA = N-octadecanoylhexadecasphinganine + CoA + H(+)

  Catalysed by DAGLB, ABHD11, DAGLA, SLC27A2 and 8 morecytosol

• (12R)-hydroxy-(5Z,8Z,10E,14Z)-eicosatetraenoateReach from here →
  1. 1-octadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycerol + H2O = 2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-glycerol + octadecanoate + H(+)
  2. fatty acid amide hydrolase (2-arachidonoylglycerol)
  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 DAGLB, ABHD11, DAGLA, FAAH and 1 morecytosol

• a 1-acyl-2-octadecanoyl-sn-glycero-3-phospho-(1D-myo-inositol)Reach from here →
  1. 1-octadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycerol + H2O = 2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-glycerol + octadecanoate + H(+)
  2. long-chain-fatty-acid-CoA ligase (stearate)
  3. a 1-acyl-sn-glycero-3-phospho-(1D-myo-inositol) + octadecanoyl-CoA = a 1-acyl-2-octadecanoyl-sn-glycero-3-phospho-(1D-myo-inositol) + CoA

  Catalysed by DAGLB, ABHD11, DAGLA, SLC27A2 and 7 morecytosol

• 14,15-epoxy-(5Z,8Z,11Z)-eicosatrienoateReach from here →
  1. 1-octadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycerol + H2O = 2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-glycerol + octadecanoate + H(+)
  2. fatty acid amide hydrolase (2-arachidonoylglycerol)
  3. unspecific monooxygenase (arachidonate)

  Catalysed by DAGLB, ABHD11, DAGLA, FAAH and 27 morecytosolOne of 4 routes

• 8,9-epoxy-(5Z,11Z,14Z)-eicosatrienoateReach from here →
  1. 1-octadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycerol + H2O = 2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-glycerol + octadecanoate + H(+)
  2. fatty acid amide hydrolase (2-arachidonoylglycerol)
  3. unspecific monooxygenase (arachidonate)

  Catalysed by DAGLB, ABHD11, DAGLA, FAAH and 26 morecytosolOne of 3 routes

• 1-heptadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphoserineReach from here →
  1. 1-octadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycerol + H2O = 2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-glycerol + octadecanoate + H(+)
  2. fatty acid amide hydrolase (2-arachidonoylglycerol)
  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 DAGLB, ABHD11, DAGLA, FAAH and 1 morecytosol

• 1-heptadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholineReach from here →
  1. 1-octadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycerol + H2O = 2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-glycerol + octadecanoate + H(+)
  2. fatty acid amide hydrolase (2-arachidonoylglycerol)
  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 DAGLB, ABHD11, DAGLA, FAAH and 1 morecytosol

• 1-heptadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphoethanolamineReach from here →
  1. 1-octadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycerol + H2O = 2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-glycerol + octadecanoate + H(+)
  2. fatty acid amide hydrolase (2-arachidonoylglycerol)
  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 DAGLB, ABHD11, DAGLA, FAAH and 1 morecytosol

• O-octadecanoyl-(R)-carnitineReach from here →
  1. 1-octadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycerol + H2O = 2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-glycerol + octadecanoate + H(+)
  2. long-chain-fatty-acid-CoA ligase (stearate)
  3. (R)-carnitine + octadecanoyl-CoA = O-octadecanoyl-(R)-carnitine + CoA

  Catalysed by DAGLB, ABHD11, DAGLA, SLC27A2 and 7 morecytosol

• beta-D-glucosyl-(1<->1)-N-octadecanoylsphing-4-enineReach from here →
  1. 1-octadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycerol + H2O = 2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-glycerol + octadecanoate + H(+)
  2. N-octadecanoylsphing-4-enine + H2O = sphing-4-enine + octadecanoate
  3. beta-D-glucosyl-(1<->1)-N-octadecanoylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-glucoside + N-octadecanoylsphing-4-enine

  Catalysed by DAGLB, ABHD11, DAGLA, ASAH1 and 3 more

• 1-octadecanoyl-2-(9Z,12Z)-octadecadienoyl-sn-glycero-3-phosphocholineReach from here →
  1. 1-octadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycerol + H2O = 2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-glycerol + octadecanoate + H(+)
  2. long-chain-fatty-acid-CoA ligase (stearate)
  3. 2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphocholine + octadecanoyl-CoA = 1-octadecanoyl-2-(9Z,12Z)-octadecadienoyl-sn-glycero-3-phosphocholine + CoA

  Catalysed by DAGLB, ABHD11, DAGLA, SLC27A2 and 7 morecytosol

• 1-octadecanoyl-2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-phosphocholineReach from here →
  1. 1-octadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycerol + H2O = 2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-glycerol + octadecanoate + H(+)
  2. long-chain-fatty-acid-CoA ligase (stearate)
  3. 2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-phosphocholine + octadecanoyl-CoA = 1-octadecanoyl-2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-phosphocholine + CoA

  Catalysed by DAGLB, ABHD11, DAGLA, SLC27A2 and 7 morecytosol

• 2-glyceryl-prostaglandin H2Reach from here →
  1. 1-octadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycerol + H2O = 2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-glycerol + octadecanoate + H(+)
  2. 2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-glycerol + 2 O2 = 2-glyceryl-prostaglandin G2
  3. 2-glyceryl-prostaglandin G2 + AH2 = 2-glyceryl-prostaglandin H2 + A + H2O

  Catalysed by DAGLB, ABHD11, DAGLA, PTGS2

• (18R)-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. 1-octadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycerol + H2O = 2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-glycerol + octadecanoate + H(+)
  2. fatty acid amide hydrolase (2-arachidonoylglycerol)
  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 DAGLB, ABHD11, DAGLA, FAAH and 1 morecytosol

• 15-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoateReach from here →
  1. 1-octadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycerol + H2O = 2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-glycerol + octadecanoate + H(+)
  2. fatty acid amide hydrolase (2-arachidonoylglycerol)
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + O2 = 15-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoate

  Catalysed by DAGLB, ABHD11, DAGLA, FAAH and 1 morecytosol

• 5-hydroperoxy-(6E,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. 1-octadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycerol + H2O = 2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-glycerol + octadecanoate + H(+)
  2. fatty acid amide hydrolase (2-arachidonoylglycerol)
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + O2 = 5-hydroperoxy-(6E,8Z,11Z,14Z)-eicosatetraenoate

  Catalysed by DAGLB, ABHD11, DAGLA, FAAH and 1 morecytosol