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

Three steps

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

  Catalysed by FAAH, SLCO1B1, SLCO1A2, SLCO1B3cytosol, extracellular spaceOne of 2 routes

• taurocholateReach 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, SLCO1B3cytosol, extracellular spaceOne of 4 routes

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

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

• gamma-Glu-AlaReach from here →
  1. fatty acid amide hydrolase (2-arachidonoylglycerol)
  2. transport of arachidonate and GSH (cytosol to extracellular)
  3. gamma-glutamyltransferase (alanine)

  Catalysed by FAAH, GGT1, GGT5, GGTLC2 and 3 morecytosol, extracellular space

• 3,3',5-triiodo-L-thyronineReach 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

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

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

• malonaldehydeReach from here →
  1. fatty acid amide hydrolase (2-arachidonoylglycerol)
  2. prostaglandin-endoperoxide synthase (arachidonate)
  3. thromboxane A synthase (12(S)-HHT)

  Catalysed by FAAH, PTGS1, PTGS2, TBXAS1cytosolOne of 2 routes

• glycineReach from here →
  1. fatty acid amide hydrolase (2-arachidonoylglycerol)
  2. N-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-glycine + H2O = (5Z,8Z,11Z,14Z)-eicosatetraenoate + glycine
  3. N-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-glycine + H2O = (5Z,8Z,11Z,14Z)-eicosatetraenoate + glycine

  Catalysed by FAAH, PM20D1cytosol

• butanoyl-CoAReach from here →
  1. fatty acid amide hydrolase (2-arachidonoylglycerol)
  2. Utilized Transport
  3. transport of butyryl-CoA and L-carnitine (cytosol to mitochondria)

  Catalysed by FAAH, SLC33A1, ESCO2, OXSMcytosol, endoplasmic reticulum, mitochondrial matrixOne of 2 routes

• prostaglandin E1Reach from here →
  1. fatty acid amide hydrolase (2-arachidonoylglycerol)
  2. transport of arachidonate (cytosol to extracellular)
  3. transport of prostaglandin E1 (cytosol to extracellular)

  Catalysed by FAAH, SLCO1B1cytosol, extracellular spaceOne of 4 routes

• prostaglandin I2Reach from here →
  1. fatty acid amide hydrolase (2-arachidonoylglycerol)
  2. transport of arachidonate (cytosol to extracellular)
  3. transport of prostaglandin I2 (cytosol to extracellular)

  Catalysed by FAAH, SLCO1B1cytosol, extracellular spaceOne of 6 routes

• prostaglandin F2alphaReach from here →
  1. fatty acid amide hydrolase (2-arachidonoylglycerol)
  2. transport of arachidonate (cytosol to extracellular)
  3. transport of prostaglandin F2alpha (cytosol to extracellular)

  Catalysed by FAAH, SLCO1B1cytosol, extracellular spaceOne of 6 routes

• prostaglandin D2Reach from here →
  1. fatty acid amide hydrolase (2-arachidonoylglycerol)
  2. transport of arachidonate (cytosol to extracellular)
  3. transport of prostaglandin D2 (cytosol to extracellular)

  Catalysed by FAAH, SLCO1B1cytosol, extracellular spaceOne of 7 routes

• (15S)-hydroxy-(5Z,8Z,11Z,13E)-eicosatetraenoateReach from here →
  1. fatty acid amide hydrolase (2-arachidonoylglycerol)
  2. arachidonate:oxygen 15-oxidoreductase
  3. Glutathione: 15-HPETE oxidoreductase

  Catalysed by FAAH, ALOX15B, ALOX15, GPX5 and 8 morecytosolOne of 4 routes

• 15-oxo-(5Z,8Z,11Z,13E)-eicosatetraenoateReach 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 = 15-oxo-(5Z,8Z,11Z,13E)-eicosatetraenoate + H2O

  Catalysed by FAAH, ALOX15B, ALOX15, ALOX12 and 7 morecytosolOne of 2 routes

• thromboxane A2Reach from here →
  1. fatty acid amide hydrolase (2-arachidonoylglycerol)
  2. prostaglandin-endoperoxide synthase (arachidonate)
  3. thromboxane A synthase (prostaglandin H2)

  Catalysed by FAAH, PTGS1, PTGS2, TBXAS1cytosol, endoplasmic reticulumOne of 2 routes

• 7,8-dihydrofolateReach from here →
  1. fatty acid amide hydrolase (2-arachidonoylglycerol)
  2. (5Z,8Z,11Z,14Z)-eicosatetraenoate + AH2 + 2 O2 = prostaglandin H2 + A + H2O
  3. uridine(34) in tRNA + 5,10-methylenetetrahydrofolate + taurine + GTP + A + H2O = 5-taurinomethyluridine(34) in tRNA + 7,8-dihydrofolate + GDP + AH2 + phosphate + H(+)

  Catalysed by FAAH, PTGS1, PTGS2, MTO1cytosol

• (R)-S-lactoylglutathioneReach from here →
  1. fatty acid amide hydrolase (2-arachidonoylglycerol)
  2. transport of arachidonate and GSH (cytosol to extracellular)
  3. (R)-S-Lactoylglutathione methylglyoxal-lyase (isomerizing)

  Catalysed by FAAH, GLO1, GLOD4cytosol, extracellular spaceOne of 2 routes

• 1-hexadecanoyl-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 + hexadecanoyl-CoA = 1-hexadecanoyl-sn-glycero-3-phosphate + CoA

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

• O-acetyl-(R)-carnitineReach from here →
  1. fatty acid amide hydrolase (2-arachidonoylglycerol)
  2. Utilized Transport
  3. Acetyl-CoA:carnitine O-acetyltransferase

  Catalysed by FAAH, CPT1A, CPT1C, CPT1Bcytosol, endoplasmic reticulumOne of 9 routes

• ethanolamineReach from here →
  1. fatty acid amide hydrolase (2-arachidonoylglycerol)
  2. fatty acylamide amidohydrolase
  3. N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-ethanolamine + H2O = ethanolamine + (5Z,8Z,11Z,14Z)-eicosatetraenoate

  Catalysed by FAAH, FAAH2cytosol

• dihydroxyacetone 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 + NAD(+) = dihydroxyacetone phosphate + NADH + H(+)

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

• S-formylglutathioneReach from here →
  1. fatty acid amide hydrolase (2-arachidonoylglycerol)
  2. transport of arachidonate and GSH (cytosol to extracellular)
  3. alcohol dehydrogenase (formaldehyde)

  Catalysed by FAAH, ADH1C, ADH1A, ADH5 and 3 morecytosol, extracellular space

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

  Catalysed by FAAH, SLCO1B1cytosol, extracellular spaceOne of 2 routes

• a 1-acyl-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 + an acyl-CoA = a 1-acyl-sn-glycero-3-phosphate + CoA

  Catalysed by FAAH, CES2, ABHD16A, EPHX1 and 15 more

• leukotriene C4Reach from here →
  1. fatty acid amide hydrolase (2-arachidonoylglycerol)
  2. transport of arachidonate (cytosol to extracellular)
  3. transport of leukotriene C4 (cytosol to extracellular)

  Catalysed by FAAH, SLCO1B1cytosol, extracellular spaceOne of 9 routes

• L-phenylalanineReach from here →
  1. fatty acid amide hydrolase (2-arachidonoylglycerol)
  2. (5Z,8Z,11Z,14Z)-eicosatetraenoate + L-phenylalanine = N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-phenylalanine + H2O
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + L-phenylalanine = N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-phenylalanine + H2O

  Catalysed by FAAH, PM20D1cytosol

• glutathione disulfideReach 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 23 routes

• taurolithocholate 3-sulfateReach 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

• CDP-glycerolReach 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. CDP-glycerol + H2O = sn-glycerol 3-phosphate + CMP + 2 H(+)

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

• an acyl-CoAReach from here →
  1. fatty acid amide hydrolase (2-arachidonoylglycerol)
  2. Arachidonate:CoA ligase (AMP-forming)
  3. acyl-CoA pool formation and breakdown

  Catalysed by FAAH, SLC27A2, ACSL4, ACSL3 and 5 morecytosol

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

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

• L-thyroxineReach 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

• (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoateReach 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

• S-sulfanylglutathioneReach from here →
  1. fatty acid amide hydrolase (2-arachidonoylglycerol)
  2. transport of arachidonate and GSH (cytosol to extracellular)
  3. Sulfide:glutathione,quinone oxidoreductase

  Catalysed by FAAH, SQORcytosol, extracellular space, mitochondrial matrix

• monodehydro-L-ascorbate radicalReach from here →
  1. fatty acid amide hydrolase (2-arachidonoylglycerol)
  2. arachidonate to 8-peroxy-(5Z,9E,11Z,14Z)-eicosatetraenoate conversion
  3. 8-peroxy-(5Z,9E,11Z,14Z)... to 5,9-cyclo-6,8-cycloperoxy-12... conversion

  Catalysed by FAAHcytosol

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

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

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

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

• glycolithocholate 3-sulfateReach 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

• a 2,3-dehydroacyl-CoAReach from here →
  1. fatty acid amide hydrolase (2-arachidonoylglycerol)
  2. (5Z,8Z,11Z,14Z)-eicosatetraenoate + AH2 + 2 O2 = prostaglandin H2 + A + H2O
  3. a 2,3-saturated acyl-CoA + A = a 2,3-dehydroacyl-CoA + AH2

  Catalysed by FAAH, PTGS1, PTGS2, ACAD10cytosol

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

  Catalysed by FAAH, SLCO1B1cytosol, extracellular spaceOne of 2 routes

• a 1,2-diacyl-sn-glycero-3-phospho-(1'-sn-glycero-3'-phosphate)Reach 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 CDP-1,2-diacyl-sn-glycerol + sn-glycerol 3-phosphate = a 1,2-diacyl-sn-glycero-3-phospho-(1'-sn-glycero-3'-phosphate) + CMP + H(+)

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

• prostaglandin E2Reach from here →
  1. fatty acid amide hydrolase (2-arachidonoylglycerol)
  2. transport of arachidonate (cytosol to extracellular)
  3. transport of prostaglandin E2 (cytosol to extracellular)

  Catalysed by FAAH, SLCO1B1, SLCO1A2, SLCO1B3cytosol, extracellular spaceOne of 7 routes

• L-cysteinylglycineReach from here →
  1. fatty acid amide hydrolase (2-arachidonoylglycerol)
  2. transport of arachidonate and GSH (cytosol to extracellular)
  3. glutathione gamma-glutamylaminopeptidase

  Catalysed by FAAH, GGTLC3, GGT1, GGT5 and 3 morecytosol, extracellular spaceOne of 4 routes

• Fe(II)-heme aReach from here →
  1. fatty acid amide hydrolase (2-arachidonoylglycerol)
  2. (5Z,8Z,11Z,14Z)-eicosatetraenoate + AH2 + 2 O2 = prostaglandin H2 + A + H2O
  3. Fe(II)-heme o + 2 A + H2O = Fe(II)-heme a + 2 AH2

  Catalysed by FAAH, PTGS1, PTGS2, COX15cytosol

• CHEBI:63544Reach from here →
  1. fatty acid amide hydrolase (2-arachidonoylglycerol)
  2. Arachidonate:CoA ligase (AMP-forming)
  3. fatty-acyl-CoA elongation (N-C20:4CoA)

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

• 5-oxo-(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 = 5-oxo-(6E,8Z,11Z,14Z)-eicosatetraenoate + H2O

  Catalysed by FAAH, ALOX5, CYP1A1, CYP1A2 and 2 morecytosol

• Mo-molybdopterinReach from here →
  1. fatty acid amide hydrolase (2-arachidonoylglycerol)
  2. (5Z,8Z,11Z,14Z)-eicosatetraenoate + AH2 + 2 O2 = prostaglandin H2 + A + H2O
  3. Mo-molybdopterin + L-cysteine + AH2 = thio-Mo-molybdopterin + L-alanine + A + H2O

  Catalysed by FAAH, PTGS1, PTGS2, MOCOScytosol

• (8Z,11Z,14Z)-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 13 routes

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

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