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

Three steps

• acetylcholineReach from here →
  1. fatty acid amide hydrolase (2-arachidonoylglycerol)
  2. transport of arachidonate (cytosol to extracellular)
  3. transport of acetylcholine (cytosol to extracellular)

  Catalysed by FAAH, SLCO1B1, SLCO1B3cytosol, extracellular spaceOne of 4 routes

• propionyl-CoAReach from here →
  1. fatty acid amide hydrolase (2-arachidonoylglycerol)
  2. Utilized Transport
  3. Active Transport

  Catalysed by FAAHcytosol, endoplasmic reticulum, mitochondrial matrixOne of 2 routes

• CHEBI:15650Reach from here →
  1. fatty acid amide hydrolase (2-arachidonoylglycerol)
  2. transport of arachidonate (cytosol to extracellular)
  3. transport of leukotriene E4 (cytosol to extracellular)

  Catalysed by FAAH, SLCO1B1cytosol, extracellular spaceOne of 4 routes

• S-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-4'-phosphopantetheineReach 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 + H2O = S-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-4'-phosphopantetheine + adenosine 3',5'-bisphosphate + 2 H(+)

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

• betaine aldehydeReach from here →
  1. fatty acid amide hydrolase (2-arachidonoylglycerol)
  2. (5Z,8Z,11Z,14Z)-eicosatetraenoate + AH2 + 2 O2 = prostaglandin H2 + A + H2O
  3. choline + A = betaine aldehyde + AH2

  Catalysed by FAAH, PTGS1, PTGS2, CHDHcytosol

• hexadecanoic acidReach 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 14 routes

• bromideReach from here →
  1. fatty acid amide hydrolase (2-arachidonoylglycerol)
  2. transport of arachidonate and GSH (cytosol to extracellular)
  3. 2-bromoacetaldehyde:glutathione S-(formylmethyl)transferase

  Catalysed by FAAH, MGST3, GSTA4, GSTA1 and 14 morecytosol, extracellular spaceOne of 2 routes

• lithocholic acidReach from here →
  1. fatty acid amide hydrolase (2-arachidonoylglycerol)
  2. transport of arachidonate (cytosol to extracellular)
  3. transport of lithocholate (cytosol to extracellular)

  Catalysed by FAAH, SLCO1B1, SLCO1A2, SLCO1B3cytosol, extracellular spaceOne of 4 routes

• oxaloacetateReach from here →
  1. fatty acid amide hydrolase (2-arachidonoylglycerol)
  2. (5Z,8Z,11Z,14Z)-eicosatetraenoate + AH2 + 2 O2 = prostaglandin H2 + A + H2O
  3. (R)-malate + A = oxaloacetate + AH2

  Catalysed by FAAH, PTGS1, PTGS2, D2HGDHcytosol

• (S)-lactateReach from here →
  1. fatty acid amide hydrolase (2-arachidonoylglycerol)
  2. prostaglandin-endoperoxide synthase (arachidonate)
  3. prostaglandin H2(out) + 2 (S)-lactate(in) = prostaglandin H2(in) + 2 (S)-lactate(out)

  Catalysed by FAAH, PTGS1, PTGS2, SLCO2A1cytosol, inner side of the membrane, outer side of the membraneOne of 2 routes

• formaldehydeReach from here →
  1. fatty acid amide hydrolase (2-arachidonoylglycerol)
  2. (5Z,8Z,11Z,14Z)-eicosatetraenoate + AH2 + 2 O2 = prostaglandin H2 + A + H2O
  3. N(6),N(6)-dimethyl-L-lysyl(4)-[histone H3] + 2 A + 2 H2O = L-lysyl(4)-[histone H3] + 2 formaldehyde + 2 AH2

  Catalysed by FAAH, PTGS1, PTGS2, KDM1A and 1 morecytosolOne of 3 routes

• sn-glycerol 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 + H2O = octadecanoate + sn-glycerol 3-phosphocholine + H(+)

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

• 1-acyl-sn-glycerol 3-phosphateReach from here →
  1. 2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-glycerol + H2O = glycerol + (5Z,8Z,11Z,14Z)-eicosatetraenoate + H(+)
  2. a monoacylglycerol + H2O = glycerol + a fatty acid + H(+)
  3. ATP:acylglycerol 3-phosphotransferase

  Catalysed by FAAH, CES2, ABHD16A, EPHX1 and 8 morecytosolOne of 6 routes

• bilirubin IXalphaReach from here →
  1. fatty acid amide hydrolase (2-arachidonoylglycerol)
  2. transport of arachidonate (cytosol to extracellular)
  3. transport of bilirubin (cytosol to extracellular)

  Catalysed by FAAH, SLCO1B1, SLCO1A2, SLCO1B3cytosol, extracellular spaceOne of 4 routes

• taurolithocholateReach 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

• CHEBI:17208Reach from here →
  1. fatty acid amide hydrolase (2-arachidonoylglycerol)
  2. transport of arachidonate and GSH (cytosol to extracellular)
  3. glutathione:dehydroascorbate oxidoreductase

  Catalysed by FAAHcytosol, extracellular space

• homocysteineReach from here →
  1. fatty acid amide hydrolase (2-arachidonoylglycerol)
  2. transport of arachidonate and GSH (cytosol to extracellular)
  3. Formation of Homocystine

  Catalysed by FAAHcytosol, extracellular space

• all-trans-retinolReach from here →
  1. fatty acid amide hydrolase (2-arachidonoylglycerol)
  2. (5Z,8Z,11Z,14Z)-eicosatetraenoate + AH2 + 2 O2 = prostaglandin H2 + A + H2O
  3. all-trans-13,14-dihydroretinol + A = all-trans-retinol + AH2

  Catalysed by FAAH, PTGS1, PTGS2, RETSATcytosol

• linoleic acidReach 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 14 routes

• O-hexadecanoyl-(R)-carnitineReach from here →
  1. fatty acid amide hydrolase (2-arachidonoylglycerol)
  2. Utilized Transport
  3. palmitoyl-CoA:L-carnitine O-palmitoyltransferase

  Catalysed by FAAH, CPT2, CPT1Acytosol, endoplasmic reticulum, peroxisomeOne of 10 routes

• AH2Reach from here →
  1. fatty acid amide hydrolase (2-arachidonoylglycerol)
  2. (5Z,8Z,11Z,14Z)-eicosatetraenoate + AH2 + 2 O2 = prostaglandin H2 + A + H2O
  3. A + NADH + H(+) = AH2 + NAD(+)

  Catalysed by FAAH, PTGS1, PTGS2, AIFM1 and 1 morecytosolOne of 19 routes

• L-cysteineReach from here →
  1. fatty acid amide hydrolase (2-arachidonoylglycerol)
  2. transport of arachidonate and GSH (cytosol to extracellular)
  3. cystine to cysteine conversion

  Catalysed by FAAHcytosol, extracellular spaceOne of 2 routes

• O-octanoyl-(R)-carnitineReach from here →
  1. fatty acid amide hydrolase (2-arachidonoylglycerol)
  2. Utilized Transport
  3. solute carrier (L-carnitine)

  Catalysed by FAAH, SLC25A20cytosol, endoplasmic reticulum, mitochondrial matrixOne of 7 routes

• dodecanoateReach 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-(9Z,12Z,15Z-octadecatrienoyl)-3-(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)-3-(9Z-octadecenoyl)-glycerol + CoA

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

• 1-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-3-(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-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholine + glycerol = 1-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-glycerol + 1-octadecanoyl-sn-glycero-3-phosphocholine
  3. 1-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-glycerol + (9Z)-octadecenoyl-CoA = 1-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-3-(9Z-octadecenoyl)-glycerol + CoA

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

• 20-O-(beta-D-glucuronosyl)-(5Z,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. fatty acid amide hydrolase (2-arachidonoylglycerol)
  2. arachidonic acid:oxygen 1-oxidoreductase
  3. 20-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoate + UDP-alpha-D-glucuronate = 20-O-(beta-D-glucuronosyl)-(5Z,8Z,11Z,14Z)-eicosatetraenoate + UDP + H(+)

  Catalysed by FAAH, CYP1A1, CYP1A2, CYP2E1 and 27 morecytosol

• (2E,5Z,8Z,11Z,14Z)-eicosatetraenoyl-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 + O2 = (2E,5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA + H2O2

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

• docosanoateReach 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

• a quinolReach 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. a quinone + sn-glycerol 3-phosphate = dihydroxyacetone phosphate + a quinol

  Catalysed by FAAH, CES2, ABHD16A, EPHX1 and 12 more

• octadecanoateReach 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 13 routes

• alpha-linolenic acidReach 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 13 routes

• elaidic acidReach 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

• all-cis-docosa-4,7,10,13,16,19-hexaenoic acidReach 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

• 5(S)-HETEReach from here →
  1. fatty acid amide hydrolase (2-arachidonoylglycerol)
  2. Arachidonate:oxygen 5-oxidoreductase
  3. Glutathione: 5-HPETE oxidoreductase

  Catalysed by FAAH, ALOX5, GPX5, GPX1 and 7 morecytosolOne of 4 routes

• CHEBI:28666Reach from here →
  1. fatty acid amide hydrolase (2-arachidonoylglycerol)
  2. transport of arachidonate (cytosol to extracellular)
  3. transport of LTD4 (cytosol to extracellular)

  Catalysed by FAAH, SLCO1B1cytosol, extracellular spaceOne of 4 routes

• a fatty acidReach from here →
  1. 2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-glycerol + H2O = glycerol + (5Z,8Z,11Z,14Z)-eicosatetraenoate + H(+)
  2. a monoacylglycerol + H2O = glycerol + a fatty acid + H(+)
  3. a monoacylglycerol + H2O = glycerol + a fatty acid + H(+)

  Catalysed by FAAH, CES2, ABHD16A, EPHX1 and 7 more

• chlorine(.)Reach from here →
  1. fatty acid amide hydrolase (2-arachidonoylglycerol)
  2. Utilized Transport
  3. Carnitine Transport by Atb0

  Catalysed by FAAH, SLC6A14cytosol, endoplasmic reticulum, extracellular space

• glycocholateReach from here →
  1. fatty acid amide hydrolase (2-arachidonoylglycerol)
  2. transport of arachidonate (cytosol to extracellular)
  3. solute carrier organic anion transporter (glycocholate)

  Catalysed by FAAH, SLCO1B1, SLCO1A2, SLCO1B3cytosol, extracellular spaceOne of 4 routes

• cholateReach from here →
  1. fatty acid amide hydrolase (2-arachidonoylglycerol)
  2. transport of arachidonate (cytosol to extracellular)
  3. solute carrier organic anion transporter (cholate)

  Catalysed by FAAH, SLCO1B1, SLCO1A2, SLCO1B3cytosol, extracellular spaceOne of 4 routes

• tetradecanoateReach 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

• (9Z)-octadecenoateReach 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 14 routes

• hexacosanoateReach 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

• tetracosanoateReach 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

• an N-acylsphinganineReach from here →
  1. fatty acid amide hydrolase (2-arachidonoylglycerol)
  2. (10Z)-heptadecenoic acid formation
  3. N-acylsphingosine amidohydrolase

  Catalysed by FAAH, ASAH1, ACER2, ACER1 and 2 morecytosol

• eicosanoateReach 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

• (9Z)-hexadecenoateReach 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 18 routes

• (15Z)-tetracosenoateReach 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

• (11Z)-eicosenoateReach 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

• serotoninReach from here →
  1. fatty acid amide hydrolase (2-arachidonoylglycerol)
  2. transport of arachidonate (cytosol to extracellular)
  3. transport of serotonin (cytosol to extracellular)

  Catalysed by FAAH, SLCO1B1, SLCO1A2, SLCO1B3cytosol, extracellular spaceOne of 4 routes