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

Three steps

• a triacylglycerolReach from here →
  1. Arachidonate:CoA ligase (AMP-forming)
  2. acyl-CoA pool formation and breakdown
  3. acyl-CoA:1,2-diacyl-sn-glycerol O-acyltransferase

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 9 morecytosol

• CHEBI:17895Reach from here →
  1. Utilized Transport
  2. Carnitine Transport by Atb0
  3. Transport of L-Tyrosine by Atb0 Transporter

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

• all-trans-retinalReach 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. retinol: NADP+ oxidoreductase

  Catalysed by PTGS1, PTGS2, RETSAT, DHRS3 and 5 morecytosolOne of 6 routes

• CHEBI:17927Reach from here →
  1. Arachidonate:CoA ligase (AMP-forming)
  2. Arachidonyl-CoA hydrolase
  3. N1,N8-diacetylspermidine to N1-acetylspermidine conversion

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 9 morecytosol

• butanoateReach from here →
  1. Utilized Transport
  2. transport of butyryl-CoA and L-carnitine (cytosol to mitochondria)
  3. butanoyl-CoA + H2O = butanoate + CoA + H(+)

  Catalysed by SLC33A1, ESCO2, OXSM, ACOT8 and 5 moreendoplasmic reticulum, cytosol, mitochondrial matrixOne of 5 routes

• 3-phenylpyruvateReach from here →
  1. (5Z,8Z,11Z,14Z)-eicosatetraenoate + L-phenylalanine = N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-phenylalanine + H2O
  2. (5Z,8Z,11Z,14Z)-eicosatetraenoate + L-phenylalanine = N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-phenylalanine + H2O
  3. Phenylalanine Transaminase, Mitochondrial

  Catalysed by PM20D1, GOT2, TATmitochondrial matrixOne of 5 routes

• CHEBI:18019Reach from here →
  1. Utilized Transport
  2. Carnitine Transport by Atb0
  3. transport of chloride and lysine (cytosol to extracellular)

  Catalysed by SLC6A14endoplasmic reticulum, cytosol, extracellular spaceOne of 7 routes

• a diacylglycerolReach 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. a triacylglycerol + all-trans-retinol = an all-trans-retinyl ester + a diacylglycerol

  Catalysed by PTGS1, PTGS2, RETSAT, PNPLA4 and 1 more

• L-glutamineReach from here →
  1. Utilized Transport
  2. Carnitine Transport by Atb0
  3. Transport of L-Glutamine by Atb0 Transporter

  Catalysed by SLC6A14endoplasmic reticulum, cytosol, extracellular spaceOne of 16 routes

• (R)-3,4-dihydroxymandelaldehydeReach from here →
  1. transport of arachidonate (cytosol to extracellular)
  2. transport of noradrenaline (cytosol to extracellular)
  3. (R)-noradrenaline + O2 + H2O = (R)-3,4-dihydroxymandelaldehyde + H2O2 + NH4(+)

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

• CHEBI:18095Reach from here →
  1. Utilized Transport
  2. Carnitine Transport by Atb0
  3. transport of trans-4-hydroxy-L-proline (cytosol to extracellular)

  Catalysed by SLC6A14, CLTRN, SLC6A20endoplasmic reticulum, cytosol, extracellular space

• CHEBI:18183Reach from here →
  1. transport of arachidonate and GSH (cytosol to extracellular)
  2. gamma-glutamyltransferase (alanine)
  3. gamma-glutamylcyclotransferase ((5-L-glutamyl)-L-amino acid)

  Catalysed by GGT1, GGT5, GGTLC2, GGT6 and 4 moreextracellular space, cytosol

• N-carbamoyl-beta-alanineReach from here →
  1. Utilized Transport
  2. Carnitine Transport by Atb0
  3. Transport of 3-Ureidopropionate

  Catalysed by SLC6A14endoplasmic reticulum, cytosol, extracellular spaceOne of 2 routes

• N(1)-(5-phospho-D-ribosyl)glycinamideReach 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. 5-Phospho-D-ribosylamine:glycine ligase (ADP-forming)

  Catalysed by FAAH, PM20D1, GARTcytosol

• 2-phenylethylamineReach from here →
  1. (5Z,8Z,11Z,14Z)-eicosatetraenoate + L-phenylalanine = N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-phenylalanine + H2O
  2. (5Z,8Z,11Z,14Z)-eicosatetraenoate + L-phenylalanine = N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-phenylalanine + H2O
  3. L-phenylalanine carboxy-lyase (phenylethylamine-forming)

  Catalysed by PM20D1, DDCcytosol

• (R)-normetanephrineReach from here →
  1. transport of arachidonate (cytosol to extracellular)
  2. transport of noradrenaline (cytosol to extracellular)
  3. S-Adenosyl-L-methionine:catechol O-methyltransferase

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

• ophthalmateReach 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. gamma-L-glutamyl-(2S)-2-aminobutanoate + glycine + ATP = ophthalmate + ADP + phosphate + H(+)

  Catalysed by FAAH, PM20D1, GSS

• S-methylmercury-L-cysteineReach from here →
  1. (5Z,8Z,11Z,14Z)-eicosatetraenoate + L-phenylalanine = N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-phenylalanine + H2O
  2. (5Z,8Z,11Z,14Z)-eicosatetraenoate + L-phenylalanine = N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-phenylalanine + H2O
  3. S-methylmercury-L-cysteine(in) + L-phenylalanine(out) = S-methylmercury-L-cysteine(out) + L-phenylalanine(in)

  Catalysed by PM20D1, SLC7A8inner side of the membrane, outer side of the membraneOne of 2 routes

• 2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phospho-(1D-myo-inositol)Reach from here →
  1. (5Z,8Z,11Z,14Z)-eicosatetraenoate + ATP + CoA = (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA + AMP + diphosphate
  2. 1-octadecanoyl-sn-glycero-3-phospho-(1D-myo-inositol) + (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA = 1-octadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phospho-(1D-myo-inositol) + CoA
  3. 1-octadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phospho-(1D-myo-inositol) + H2O = 2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phospho-(1D-myo-inositol) + octadecanoate + H(+)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 9 moreOne of 3 routes

• (5S)-hydroperoxy-(6E,8Z,11Z,14Z,17Z)-eicosapentaenoateReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate + O2 = (5S)-hydroperoxy-(6E,8Z,11Z,14Z,17Z)-eicosapentaenoate

  Catalysed by ALOX5cytosol, extracellular space

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

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

• 5-(3,3-dimethylguanidino)-2-oxopentanoateReach from here →
  1. (5Z,8Z,11Z,14Z)-eicosatetraenoate + AH2 + 2 O2 = prostaglandin H2 + A + H2O
  2. (R)-malate + A = oxaloacetate + AH2
  3. N(omega),N(omega)-dimethyl-L-arginine + oxaloacetate = 5-(3,3-dimethylguanidino)-2-oxopentanoate + L-aspartate

  Catalysed by PTGS1, PTGS2, D2HGDH, AGXT2

• N(omega),N('omega)-dimethyl-L-arginineReach 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. N(omega),N('omega)-dimethyl-L-arginine + glyoxylate = 5-(3,3'-dimethylguanidino)-2-oxopentanoate + glycine

  Catalysed by FAAH, PM20D1, AGXT2

• 1-butanoyl-2-(9Z-octadecenoyl)-glycerolReach from here →
  1. Utilized Transport
  2. transport of butyryl-CoA and L-carnitine (cytosol to mitochondria)
  3. 2-(9Z-octadecenoyl)-glycerol + butanoyl-CoA = 1-butanoyl-2-(9Z-octadecenoyl)-glycerol + CoA

  Catalysed by SLC33A1, ESCO2, OXSM, MOGAT2 and 1 moreendoplasmic reticulum, cytosol, mitochondrial matrix

• (6R)-5,10-methylenetetrahydrofolic acidReach from here →
  1. (5Z,8Z,11Z,14Z)-eicosatetraenoate + AH2 + 2 O2 = prostaglandin H2 + A + H2O
  2. N(6),N(6)-dimethyl-L-lysyl(4)-[histone H3] + 2 A + 2 H2O = L-lysyl(4)-[histone H3] + 2 formaldehyde + 2 AH2
  3. formaldehyde to 5,10-methylene-THF conversion

  Catalysed by PTGS1, PTGS2, KDM1A, KDM1Bcytosol

• 5,6,7,8-tetrahydrofolic acidReach from here →
  1. transport of arachidonate and GSH (cytosol to extracellular)
  2. Formation of Homocystine
  3. 5-methyltetrahydrofolate:L-homocysteine S-methyltransferase

  Catalysed by MTRextracellular space, cytosolOne of 6 routes

• O-butanoyl-(R)-carnitineReach from here →
  1. Utilized Transport
  2. transport of butyryl-CoA and L-carnitine (cytosol to mitochondria)
  3. butanoyl-CoA + (R)-carnitine = O-butanoyl-(R)-carnitine + CoA

  Catalysed by SLC33A1, ESCO2, OXSM, CRATendoplasmic reticulum, cytosol, mitochondrial matrix

• S-disulfanyl-L-cysteineReach from here →
  1. transport of arachidonate and GSH (cytosol to extracellular)
  2. cystine to cysteine conversion
  3. S-sulfanyl-L-cysteine + L-cysteine = S-disulfanyl-L-cysteine + L-alanine

  Catalysed by CARS2extracellular space, cytosol

• (5Z)-dodecenoyl-CoAReach from here →
  1. Arachidonate:CoA ligase (AMP-forming)
  2. Arachidonyl-CoA hydrolase
  3. acetyl-CoA C-acyltransferase (3-oxomyrist-7-enoyl-CoA)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 12 morecytosol, mitochondrial matrixOne of 2 routes

• 15-O-(beta-D-glucuronosyl)-prostaglandin B1Reach from here →
  1. transport of arachidonate (cytosol to extracellular)
  2. transport of prostaglandin B1 (cytosol to extracellular)
  3. prostaglandin B1 + UDP-alpha-D-glucuronate = 15-O-(beta-D-glucuronosyl)-prostaglandin B1 + UDP + H(+)

  Catalysed by SLCO1B1, UGT1A9, UGT2B7, UGT1A1 and 1 moreextracellular space, cytosol

• (S)-lactoyl-AMPReach 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 + ATP + H(+) = (S)-lactoyl-AMP + diphosphate

  Catalysed by PTGS1, PTGS2, SLCO2A1, AARS1 and 1 morecytosol, inner side of the membrane, outer side of the membrane

• (S)-lactoyl-CoAReach 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 + ATP + CoA = (S)-lactoyl-CoA + AMP + diphosphate

  Catalysed by PTGS1, PTGS2, SLCO2A1, ACSS2cytosol, inner side of the membrane, outer side of the membrane

• 3-iodothyronamineReach from here →
  1. (5Z,8Z,11Z,14Z)-eicosatetraenoate + AH2 + 2 O2 = prostaglandin H2 + A + H2O
  2. A + NADH + H(+) = AH2 + NAD(+)
  3. 3-iodothyronamine + iodide + A + H(+) = 3,5-diiodothyronamine + AH2

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

• (11Z)-docosenoyl-CoA(4-)Reach from here →
  1. Arachidonate:CoA ligase (AMP-forming)
  2. Arachidonyl-CoA hydrolase
  3. long-chain-fatty-acid-CoA ligase (cis-cetoleic acid)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 9 morecytosolOne of 6 routes

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

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

• (7Z)-tetradecenoyl-CoAReach from here →
  1. Arachidonate:CoA ligase (AMP-forming)
  2. Arachidonyl-CoA hydrolase
  3. long-chain-fatty-acid-CoA ligase ((7Z)-tetradecenoic acid)

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

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

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

• serotonin O-sulfateReach from here →
  1. transport of arachidonate (cytosol to extracellular)
  2. transport of serotonin (cytosol to extracellular)
  3. serotonin + 3'-phosphoadenylyl sulfate = serotonin O-sulfate + adenosine 3',5'-bisphosphate + H(+)

  Catalysed by SLCO1B1, SLCO1A2, SLCO1B3, SULT1A3 and 1 moreextracellular space, cytosol

• (R)-noradrenaline 4'-O-sulfateReach from here →
  1. transport of arachidonate (cytosol to extracellular)
  2. transport of noradrenaline (cytosol to extracellular)
  3. sulfotransferase (noradrenaline)

  Catalysed by SLCO1B1, SLCO1A2, SLCO1B3, SULT1A3extracellular space, cytosolOne of 2 routes

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

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

• thyronamineReach from here →
  1. (5Z,8Z,11Z,14Z)-eicosatetraenoate + AH2 + 2 O2 = prostaglandin H2 + A + H2O
  2. A + NADH + H(+) = AH2 + NAD(+)
  3. thyronamine + iodide + A + H(+) = 3-iodothyronamine + AH2

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

• 3'-iodothyronamineReach from here →
  1. (5Z,8Z,11Z,14Z)-eicosatetraenoate + AH2 + 2 O2 = prostaglandin H2 + A + H2O
  2. A + NADH + H(+) = AH2 + NAD(+)
  3. 3'-iodothyronamine + iodide + A + H(+) = 3',5'-diiodothyronamine + AH2

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

• 3,3'-diiodothyronamineReach from here →
  1. (5Z,8Z,11Z,14Z)-eicosatetraenoate + AH2 + 2 O2 = prostaglandin H2 + A + H2O
  2. A + NADH + H(+) = AH2 + NAD(+)
  3. 3,3'-diiodothyronamine + iodide + A + H(+) = 3,3',5'-triiodothyronamine + AH2

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

• 3',5'-diiodothyronamineReach from here →
  1. (5Z,8Z,11Z,14Z)-eicosatetraenoate + AH2 + 2 O2 = prostaglandin H2 + A + H2O
  2. A + NADH + H(+) = AH2 + NAD(+)
  3. 3',5'-diiodothyronamine + iodide + A + H(+) = 3,3',5'-triiodothyronamine + AH2

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

• 3,3',5'-triiodothyronamineReach 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'-triiodothyronamine + iodide + A + H(+) = 3,3',5,5'-tetraiodothyronamine + AH2

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

• L-homocysteine thiolactoneReach from here →
  1. transport of arachidonate and GSH (cytosol to extracellular)
  2. Formation of Homocystine
  3. arylesterase (homocysteine-thiolactone)

  Catalysed by PON1, PON2, PON3extracellular space, cytosol

• (4Z,7Z,10Z,13Z)-hexadecatetraenoyl-CoAReach from here →
  1. Arachidonate:CoA ligase (AMP-forming)
  2. Arachidonyl-CoA hydrolase
  3. Fatty Acid Beta Oxidation (C18:4->C16:4), Mitochondrial

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 12 morecytosol, mitochondrial matrixOne of 3 routes

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

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

• (4Z,7Z)-decadienoyl-CoAReach from here →
  1. Arachidonate:CoA ligase (AMP-forming)
  2. Arachidonyl-CoA hydrolase
  3. Fatty Acid Beta Oxidation (C12:3->C10:2), Mitochondrial

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 12 morecytosol, mitochondrial matrixOne of 2 routes

• (5Z)-octenoyl-CoAReach from here →
  1. Arachidonate:CoA ligase (AMP-forming)
  2. Arachidonyl-CoA hydrolase
  3. Fatty Acid Beta Oxidation (C10:2->C8:1), Mitochondrial

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 12 morecytosol, mitochondrial matrixOne of 2 routes