(5Z,8Z,11Z,14Z)-eicosatetraenoate

Three steps

• CHEBI:16566Reach from here →
  1. (10Z)-heptadecenoic acid formation
  2. N-acylsphingosine amidohydrolase
  3. N-acylsphingosine amidohydrolase

  Catalysed by ASAH1, ACER2, ACER1, ASAH2 and 1 morecytosol

• 3'-deoxy-3',4'-didehydro-CTPReach from here →
  1. (5Z,8Z,11Z,14Z)-eicosatetraenoate + AH2 + 2 O2 = prostaglandin H2 + A + H2O
  2. A + NADH + H(+) = AH2 + NAD(+)
  3. CTP + AH2 + S-adenosyl-L-methionine = 3'-deoxy-3',4'-didehydro-CTP + 5'-deoxyadenosine + L-methionine + A + H2O + H(+)

  Catalysed by PTGS1, PTGS2, AIFM1, PYROXD1 and 1 more

• taurochenodeoxycholate 3-sulfateReach from here →
  1. transport of arachidonate (cytosol to extracellular)
  2. solute carrier organic anion transporter (S-glutathionyl-2-4-dinitrobenzene)
  3. taurochenodeoxycholate + 3'-phosphoadenylyl sulfate = taurochenodeoxycholate 3-sulfate + adenosine 3',5'-bisphosphate + H(+)

  Catalysed by SLCO1B1, SLCO1A2, SLC7A9, SLCO1B3 and 1 moreextracellular space, cytosol

• dopamine quinoneReach from here →
  1. transport of arachidonate (cytosol to extracellular)
  2. transport of dopamine (cytosol to extracellular)
  3. Peroxidase

  Catalysed by SLCO1B1, SLCO1A2, SLCO1B3, MPOextracellular space, cytosol, lysosomeOne of 4 routes

• N-[(S)-lactoyl]-L-phenylalanineReach from here →
  1. prostaglandin-endoperoxide synthase (arachidonate)
  2. prostaglandin H2(out) + 2 (S)-lactate(in) = prostaglandin H2(in) + 2 (S)-lactate(out)
  3. (S)-lactate + L-phenylalanine = N-[(S)-lactoyl]-L-phenylalanine + H2O

  Catalysed by PTGS1, PTGS2, SLCO2A1, CNDP2cytosol, inner side of the membrane, outer side of the membraneOne of 2 routes

• 8-hydroxydodecanoateReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. dodecanoate + reduced [NADPH--hemoprotein reductase] + O2 = 8-hydroxydodecanoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by CYP4Z1cytosol, extracellular space

• 10-hydroxydodecanoateReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. dodecanoate + reduced [NADPH--hemoprotein reductase] + O2 = 10-hydroxydodecanoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by CYP4Z1cytosol, extracellular space

• 9-hydroxydodecanoateReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. dodecanoate + reduced [NADPH--hemoprotein reductase] + O2 = 9-hydroxydodecanoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by CYP4Z1cytosol, extracellular space

• 9-hydroxytetradecanoateReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. tetradecanoate + reduced [NADPH--hemoprotein reductase] + O2 = 9-hydroxytetradecanoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by CYP4Z1cytosol, extracellular space

• 10-hydroxytetradecanoateReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. tetradecanoate + reduced [NADPH--hemoprotein reductase] + O2 = 10-hydroxytetradecanoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by CYP4Z1cytosol, extracellular space

• 12-hydroxytetradecanoateReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. tetradecanoate + reduced [NADPH--hemoprotein reductase] + O2 = 12-hydroxytetradecanoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by CYP4Z1cytosol, extracellular space

• 11-hydroxytetradecanoateReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. tetradecanoate + reduced [NADPH--hemoprotein reductase] + O2 = 11-hydroxytetradecanoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by CYP4Z1cytosol, extracellular space

• (S)-2-hydroxyglutarateReach from here →
  1. (5Z,8Z,11Z,14Z)-eicosatetraenoate + AH2 + 2 O2 = prostaglandin H2 + A + H2O
  2. A + NADH + H(+) = AH2 + NAD(+)
  3. (S)-2-hydroxyglutarate + A = 2-oxoglutarate + AH2

  Catalysed by PTGS1, PTGS2, AIFM1, PYROXD1 and 1 more

• CHEBI:16857Reach from here →
  1. Utilized Transport
  2. Carnitine Transport by Atb0
  3. Transport of L-Threonine by Atb0 Transporter

  Catalysed by SLC6A14endoplasmic reticulum, cytosol, extracellular spaceOne of 13 routes

• glyoxylic acidReach from here →
  1. N-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-glycine + H2O = (5Z,8Z,11Z,14Z)-eicosatetraenoate + glycine
  2. N-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-glycine + H2O = (5Z,8Z,11Z,14Z)-eicosatetraenoate + glycine
  3. glycine:oxygen oxidoreductase (deaminating)

  Catalysed by FAAH, PM20D1, DAOperoxisome

• 1-acyl-sn-glycerol 3-phosphateReach from here →
  1. Arachidonate:CoA ligase (AMP-forming)
  2. glycerol-3-phosphate 1-O-acyltransferase (arachidonyl-CoA)
  3. 1-acylglycerol-3P-LD-TG1 pool (liver tissue) formation

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 8 morecytosolOne of 9 routes

• oxalic acidReach from here →
  1. Utilized Transport
  2. Carnitine Transport by Atb0
  3. transport of chloride and oxalate (cytosol to extracellular)

  Catalysed by SLC6A14, SLC26A6endoplasmic reticulum, cytosol, extracellular space

• a cholesterol esterReach from here →
  1. Arachidonate:CoA ligase (AMP-forming)
  2. acyl-CoA pool formation and breakdown
  3. an acyl-CoA + cholesterol = a cholesterol ester + CoA

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 6 morecytosol

• octadecanalReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. octadecanal + NAD(+) + H2O = octadecanoate + NADH + 2 H(+)

  Catalysed by ALDH3A2cytosol, extracellular space

• (R)-lactaldehydeReach from here →
  1. transport of arachidonate and GSH (cytosol to extracellular)
  2. (R)-S-Lactoylglutathione methylglyoxal-lyase (isomerizing)
  3. (R)-Lactaldehyde:NAD+ oxidoreductase (glutathione-formylating)

  Catalysed by GLO1, GLOD4, ADH1C, ADH1A and 5 moreextracellular space, cytosol

• L-isoleucineReach from here →
  1. Utilized Transport
  2. Carnitine Transport by Atb0
  3. transport of chloride and isoleucine (cytosol to extracellular)

  Catalysed by SLC6A14endoplasmic reticulum, cytosol, extracellular spaceOne of 15 routes

• CHEBI:17203Reach from here →
  1. Utilized Transport
  2. Carnitine Transport by Atb0
  3. Transport of L-Proline by the Apical Imino Amino Acid Transporters

  Catalysed by SLC6A14, CLTRN, SLC6A20endoplasmic reticulum, cytosol, extracellular spaceOne of 10 routes

• dehydroascorbic acidReach from here →
  1. arachidonate to 8-peroxy-(5Z,9E,11Z,14Z)-eicosatetraenoate conversion
  2. 8-peroxy-(5Z,9E,11Z,14Z)... to 5,9-cyclo-6,8-cycloperoxy-12... conversion
  3. prostaglandin-F synthase (monodehydroascorbate)

  No catalyst recordedcytosolOne of 21 routes

• estroneReach from here →
  1. transport of arachidonate (cytosol to extracellular)
  2. transport of estrone 3-sulfate (cytosol to extracellular)
  3. Estrone 3-sulfate sulfohydrolase

  Catalysed by SLCO1B1, STSextracellular space, cytosolOne of 3 routes

• propanoateReach from here →
  1. transport of arachidonate (cytosol to extracellular)
  2. transport of estrone 3-sulfate (cytosol to extracellular)
  3. propanoate(in) + estrone 3-sulfate(out) = propanoate(out) + estrone 3-sulfate(in)

  Catalysed by SLCO1B1, SLC22A9extracellular space, cytosol, inner side of the membrane, outer side of the membraneOne of 4 routes

• anilineReach from here →
  1. Arachidonate:CoA ligase (AMP-forming)
  2. Arachidonyl-CoA hydrolase
  3. Acetyl-CoA:arylamine N-acetyltransferase

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 11 morecytosol

• CHEBI:17312Reach from here →
  1. Arachidonate:CoA ligase (AMP-forming)
  2. Arachidonyl-CoA hydrolase
  3. N1,N12-diacetylspermine to N1-acetylspermine conversion

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 9 morecytosolOne of 2 routes

• 5'-deoxyadenosineReach from here →
  1. (5Z,8Z,11Z,14Z)-eicosatetraenoate + AH2 + 2 O2 = prostaglandin H2 + A + H2O
  2. A + NADH + H(+) = AH2 + NAD(+)
  3. N(6)-dimethylallyladenosine(37) in tRNA + (sulfur carrier)-SH + AH2 + 2 S-adenosyl-L-methionine = 2-methylsulfanyl-N(6)-dimethylallyladenosine(37) in tRNA + (sulfur carrier)-H + 5'-deoxyadenosine + L-methionine + A + S-adenosyl-L-homocysteine + 2 H(+)

  Catalysed by PTGS1, PTGS2, AIFM1, PYROXD1 and 1 moreOne of 4 routes

• sulfiteReach from here →
  1. transport of arachidonate and GSH (cytosol to extracellular)
  2. Sulfide:glutathione,quinone oxidoreductase
  3. Persulfide dioxygenase

  Catalysed by SQOR, ETHE1extracellular space, cytosol, mitochondrial matrixOne of 2 routes

• D-glyceraldehydeReach from here →
  1. fatty acid amide hydrolase (2-arachidonoylglycerol)
  2. 2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-glycerol + H2O = glycerol + (5Z,8Z,11Z,14Z)-eicosatetraenoate + H(+)
  3. glycerol + NADP(+) = D-glyceraldehyde + NADPH + H(+)

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

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

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

• 1-(alk-1-enyl)-2-acyl-sn-glycero-3-phosphoethanolamineReach from here →
  1. Arachidonate:CoA ligase (AMP-forming)
  2. acyl-CoA pool formation and breakdown
  3. Acyl-CoA:1-alkenylglycerophosphoethanolamine O-acyltransferase

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 8 morecytosol

• 1-O-acyl-sn-glycero-3-phosphocholine(1+)Reach from here →
  1. (5Z,8Z,11Z,14Z)-eicosatetraenoate + AH2 + 2 O2 = prostaglandin H2 + A + H2O
  2. all-trans-13,14-dihydroretinol + A = all-trans-retinol + AH2
  3. Lecithin Retinol Acyltransferase

  Catalysed by PTGS1, PTGS2, RETSAT, LRATcytosol

• 5-aminolevulinic acidReach from here →
  1. N-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-glycine + H2O = (5Z,8Z,11Z,14Z)-eicosatetraenoate + glycine
  2. N-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-glycine + H2O = (5Z,8Z,11Z,14Z)-eicosatetraenoate + glycine
  3. succinyl-CoA:glycine C-succinyltransferase (decarboxylating)

  Catalysed by FAAH, PM20D1, ALAS1, ALAS2 and 1 moremitochondrial matrix

• O-phosphoethanolamineReach from here →
  1. fatty acylamide amidohydrolase
  2. N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-ethanolamine + H2O = ethanolamine + (5Z,8Z,11Z,14Z)-eicosatetraenoate
  3. ATP:ethanolamine O-phosphotransferase

  Catalysed by FAAH, FAAH2, CHKA, ETNK1 and 2 morecytosol

• hexadecanalReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. 2 H+[c] + NADH[c] + palmitate[c] = H2O[c] + hexadecanal[c] + NAD+[c]

  Catalysed by ALDH3B1, ALDH3B2, ALDH3A2cytosol, extracellular spaceOne of 2 routes

• all-trans-retinyl hexadecanoateReach from here →
  1. (5Z,8Z,11Z,14Z)-eicosatetraenoate + AH2 + 2 O2 = prostaglandin H2 + A + H2O
  2. all-trans-13,14-dihydroretinol + A = all-trans-retinol + AH2
  3. all-trans-retinol + hexadecanoyl-CoA = all-trans-retinyl hexadecanoate + CoA

  Catalysed by PTGS1, PTGS2, RETSAT, DGAT1 and 4 moreOne of 2 routes

• 3,3',5-triiodo-L-thyronine sulfateReach from here →
  1. transport of arachidonate (cytosol to extracellular)
  2. transport of S-glutathionyl-2-4-dinitrobenzene (cytosol to extracellular)
  3. aryl sulfotransferase (PAPS)

  Catalysed by SLCO1B1, SLCO1A2, SLCO1B3, SULT1A3 and 3 moreextracellular space, cytosolOne of 2 routes

• L-thyroxine sulfateReach from here →
  1. transport of arachidonate (cytosol to extracellular)
  2. transport of S-glutathionyl-2-4-dinitrobenzene (cytosol to extracellular)
  3. L-thyroxine + 3'-phosphoadenylyl sulfate = L-thyroxine sulfate + adenosine 3',5'-bisphosphate + H(+)

  Catalysed by SLCO1B1, SLCO1A2, SLCO1B3, SULT1A3 and 2 moreextracellular space, cytosol

• 3,3',5'-triiodo-L-thyronine sulfateReach from here →
  1. (5Z,8Z,11Z,14Z)-eicosatetraenoate + AH2 + 2 O2 = prostaglandin H2 + A + H2O
  2. A + NADH + H(+) = AH2 + NAD(+)
  3. 3,3',5'-triiodo-L-thyronine sulfate + iodide + A + H(+) = L-thyroxine sulfate + AH2

  Catalysed by PTGS1, PTGS2, AIFM1, PYROXD1 and 1 more

• 3,3'-diiodo-L-thyronineReach from here →
  1. transport of arachidonate (cytosol to extracellular)
  2. transport of S-glutathionyl-2-4-dinitrobenzene (cytosol to extracellular)
  3. thyroxine 5'-deiodinase (3,3-diiodo-L-thyronine)

  Catalysed by SLCO1B1, SLCO1A2, SLCO1B3, DIO1 and 2 moreextracellular space, cytosolOne of 5 routes

• 3,3'-diiodo-L-thyronine sulfateReach from here →
  1. (5Z,8Z,11Z,14Z)-eicosatetraenoate + AH2 + 2 O2 = prostaglandin H2 + A + H2O
  2. A + NADH + H(+) = AH2 + NAD(+)
  3. 3,3'-diiodo-L-thyronine sulfate + iodide + A + H(+) = 3,3',5-triiodo-L-thyronine sulfate + AH2

  Catalysed by PTGS1, PTGS2, AIFM1, PYROXD1 and 1 moreOne of 2 routes

• N-acetylserotoninReach from here →
  1. transport of arachidonate (cytosol to extracellular)
  2. transport of serotonin (cytosol to extracellular)
  3. acetyl-CoA:aralkylamine N-acetyltransferase

  Catalysed by SLCO1B1, SLCO1A2, SLCO1B3, AANATextracellular space, cytosol

• (7Z,10Z,13Z)-hexadecatrienoyl-CoAReach from here →
  1. Arachidonate:CoA ligase (AMP-forming)
  2. Arachidonyl-CoA hydrolase
  3. Fatty Acid Beta Oxidation (C18:3->C16:3), Mitochondrial

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 12 morecytosol, mitochondrial matrix

• CHEBI:17724Reach from here →
  1. transport of arachidonate and GSH (cytosol to extracellular)
  2. Formation of Homocystine
  3. Trimethylaminoacetate:L-homosysteine S-methyltransferase

  Catalysed by BHMT, BHMT2extracellular space, cytosolOne of 2 routes

• glycine betaineReach from here →
  1. Utilized Transport
  2. Carnitine Transport by Atb0
  3. transport of betaine and chloride (cytosol to extracellular)

  Catalysed by SLC6A14, SLC6A12endoplasmic reticulum, cytosol, extracellular spaceOne of 7 routes

• urateReach from here →
  1. transport of arachidonate and GSH (cytosol to extracellular)
  2. glutathione:dehydroascorbate oxidoreductase
  3. ascorbate to monodehydroascorbate conversion

  No catalyst recordedextracellular space, cytosolOne of 2 routes

• 5-hydroxy-L-tryptophanReach from here →
  1. transport of arachidonate (cytosol to extracellular)
  2. transport of serotonin (cytosol to extracellular)
  3. 5-hydroxy-L-tryptophan + H(+) = serotonin + CO2

  Catalysed by SLCO1B1, SLCO1A2, SLCO1B3, DDCextracellular space, cytosol

• prostaglandin F1Reach from here →
  1. transport of arachidonate (cytosol to extracellular)
  2. transport of prostaglandin E1 (cytosol to extracellular)
  3. prostaglandin E1 + NADPH + H(+) = prostaglandin F1 + NADP(+)

  Catalysed by SLCO1B1, DHRS1extracellular space, cytosol

• a 1,2-diacyl-sn-glycerolReach from here →
  1. Arachidonate:CoA ligase (AMP-forming)
  2. acyl-CoA pool formation and breakdown
  3. a 2-acylglycerol + an acyl-CoA = a 1,2-diacyl-sn-glycerol + CoA

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 7 morecytosolOne of 3 routes