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

Three steps

• (7Z)-octadecenoyl-CoAReach from here →
  1. Arachidonate:CoA ligase (AMP-forming)
  2. Arachidonyl-CoA hydrolase
  3. carnitine O-palmitoyltransferase ((7Z)-octadecenoyl-CoA)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 12 morecytosolOne of 4 routes

• acetaldehydeReach from here →
  1. fatty acylamide amidohydrolase
  2. N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-ethanolamine + H2O = ethanolamine + (5Z,8Z,11Z,14Z)-eicosatetraenoate
  3. ethanolamine ammonia-lyase (acetaldehyde-forming)

  Catalysed by FAAH, FAAH2cytosol

• CHEBI:15345Reach from here →
  1. Arachidonate:CoA ligase (AMP-forming)
  2. Arachidonyl-CoA hydrolase
  3. Acetoacetate:CoA ligase (AMP-forming)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 10 morecytosolOne of 2 routes

• cholineReach from here →
  1. Arachidonate:CoA ligase (AMP-forming)
  2. Arachidonyl-CoA hydrolase
  3. Acetyl-CoA:choline O-acetyltransferase

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 10 morecytosol, nucleusOne of 7 routes

• pyruvateReach from here →
  1. transport of arachidonate and GSH (cytosol to extracellular)
  2. cystine to cysteine conversion
  3. L-cysteine hydrogen-sulfide-lyase (deaminating

  Catalysed by CTHextracellular space, cytosolOne of 7 routes

• 4a-hydroxytetrahydrobiopterinReach 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,tetrahydrobiopterin:oxygen oxidoreductase(4-hydroxylating)

  Catalysed by PM20D1, PAHcytosol

• CHEBI:15380Reach from here →
  1. Arachidonate:CoA ligase (AMP-forming)
  2. Arachidonyl-CoA hydrolase
  3. 5-aminolevulinate synthase (2-amino-3-oxoadipate)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 11 morecytosol, mitochondrial matrixOne of 8 routes

• CHEBI:15477Reach from here →
  1. Arachidonate:CoA ligase (AMP-forming)
  2. Arachidonyl-CoA hydrolase
  3. glycine N-acyltransferase (2-methylbutyryl-CoA)

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

• 2-methylcrotonoyl-CoAReach from here →
  1. Arachidonate:CoA ligase (AMP-forming)
  2. Arachidonyl-CoA hydrolase
  3. Production of Tiglylcarnitine

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 11 morecytosolOne of 2 routes

• isobutyryl-CoAReach from here →
  1. Arachidonate:CoA ligase (AMP-forming)
  2. Arachidonyl-CoA hydrolase
  3. acetyl-CoA C-acyltransferase (3-oxo-4-methyl-pentanoyl-CoA)

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

• 3-methylbut-2-enoyl-CoAReach from here →
  1. Arachidonate:CoA ligase (AMP-forming)
  2. Arachidonyl-CoA hydrolase
  3. glycine-N-acyltransferase (3-methylcrotonoylglycine)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 10 morecytosol, mitochondrial matrix

• isovaleryl-CoAReach from here →
  1. Arachidonate:CoA ligase (AMP-forming)
  2. Arachidonyl-CoA hydrolase
  3. glycine N-acyltransferase (isovalerylglycine)

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

• CHEBI:15519Reach from here →
  1. Arachidonate:CoA ligase (AMP-forming)
  2. Arachidonyl-CoA hydrolase
  3. propanoyl-CoA C-acyltransferase

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

• palmitoyl-CoAReach from here →
  1. Arachidonate:CoA ligase (AMP-forming)
  2. Arachidonyl-CoA hydrolase
  3. Palmitate:CoA ligase (AMP-forming)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 9 morecytosolOne of 19 routes

• oleoyl-CoAReach from here →
  1. Arachidonate:CoA ligase (AMP-forming)
  2. Arachidonyl-CoA hydrolase
  3. Transport of octadecenoyl-CoA into Mitochondrial Matrix

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 12 morecytosolOne of 15 routes

• phenylacetyl-CoAReach from here →
  1. Arachidonate:CoA ligase (AMP-forming)
  2. Arachidonyl-CoA hydrolase
  3. Phenylacetate:CoA ligase

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

• CHEBI:15570Reach 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. transport of D-alanine and glycine (cytosol to extracellular)

  Catalysed by FAAH, PM20D1, SLC3A2, SLC7A10extracellular space, cytosolOne of 2 routes

• (S)-malateReach from here →
  1. (5Z,8Z,11Z,14Z)-eicosatetraenoate + AH2 + 2 O2 = prostaglandin H2 + A + H2O
  2. (R)-malate + A = oxaloacetate + AH2
  3. transport of malate and OAA (cytosol to mitochondria)

  Catalysed by PTGS1, PTGS2, D2HGDHmitochondrial matrix, cytosolOne of 5 routes

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

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

• (7S)-hydroperoxy-(4Z,8E,10Z,13Z,16Z,19Z)-docosahexaenoateReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoate + O2 = (7S)-hydroperoxy-(4Z,8E,10Z,13Z,16Z,19Z)-docosahexaenoate

  Catalysed by ALOX5cytosol, extracellular space

• CHEBI:15611Reach 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. S-Adenosyl-L-methionine:glycine N-methyltransferase

  Catalysed by FAAH, PM20D1, GNMTcytosol

• (11S)-hydroperoxy-(4Z,7Z,9E,13Z,16Z,19Z)-docosahexaenoateReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoate + O2 = (11S)-hydroperoxy-(4Z,7Z,9E,13Z,16Z,19Z)-docosahexaenoate

  Catalysed by ALOX15cytosol, extracellular space

• (4aS,6R)-4a-hydroxy-L-erythro-5,6,7,8-tetrahydrobiopterinReach 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. (6R)-L-erythro-5,6,7,8-tetrahydrobiopterin + L-phenylalanine + O2 = (4aS,6R)-4a-hydroxy-L-erythro-5,6,7,8-tetrahydrobiopterin + L-tyrosine

  Catalysed by PM20D1, PAH

• all-trans-3-hydroxyretinolReach 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 + 2 reduced [adrenodoxin] + O2 + 2 H(+) = all-trans-3-hydroxyretinol + 2 oxidized [adrenodoxin] + H2O

  Catalysed by PTGS1, PTGS2, RETSAT, CYP27C1

• CHEBI:15699Reach from here →
  1. transport of arachidonate and GSH (cytosol to extracellular)
  2. cystine to cysteine conversion
  3. transport of cysteine and homoserine (cytosol to extracellular)

  Catalysed by SLC7A5extracellular space, cytosolOne of 10 routes

• CHEBI:15727Reach from here →
  1. Arachidonate:CoA ligase (AMP-forming)
  2. Arachidonyl-CoA hydrolase
  3. N-alpha-acetyltransferase 10, NatA catalytic subunit (acetylcarnosine)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 10 morecytosol

• formateReach from here →
  1. transport of arachidonate and GSH (cytosol to extracellular)
  2. alcohol dehydrogenase (formaldehyde)
  3. S-formylglutathione + H2O = formate + glutathione + H(+)

  Catalysed by ADH1C, ADH1A, ADH5, ADH6 and 3 moreextracellular space, cytosolOne of 2 routes

• CHEBI:15746Reach from here →
  1. Arachidonate:CoA ligase (AMP-forming)
  2. Arachidonyl-CoA hydrolase
  3. diamine N-acetyltransferase (N1-acetylspermine)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 11 morecytosolOne of 2 routes

• 1-acylglycerone 3-phosphateReach from here →
  1. Arachidonate:CoA ligase (AMP-forming)
  2. acyl-CoA pool formation and breakdown
  3. Acyl-CoA:glycerone-phosphate O-acyltransferase

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 5 morecytosol

• CHEBI:15971Reach from here →
  1. Utilized Transport
  2. Carnitine Transport by Atb0
  3. transport of chloride and histidine (cytosol to extracellular)

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

• (R)-lactateReach from here →
  1. transport of arachidonate and GSH (cytosol to extracellular)
  2. (R)-S-Lactoylglutathione methylglyoxal-lyase (isomerizing)
  3. (R)-S-lactoylglutathione + H2O = (R)-lactate + glutathione + H(+)

  Catalysed by GLO1, GLOD4, HAGHextracellular space, cytosol

• methanethiolReach 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. methanethiol + O2 + H2O = hydrogen sulfide + formaldehyde + H2O2 + H(+)

  Catalysed by PTGS1, PTGS2, KDM1A, KDM1B and 1 more

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

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

• 1,2-diacyl-sn-glycero-3-phosphocholine(1+)Reach from here →
  1. Arachidonate:CoA ligase (AMP-forming)
  2. acyl-CoA pool formation and breakdown
  3. Acyl-CoA:1-acyl-sn-glycero-3-phosphocholine O-acyltransferase

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

• octan-1-olReach from here →
  1. transport of arachidonate (cytosol to extracellular)
  2. solute carrier organic anion transporter (chenodiol)
  3. octyl beta-D-glucose + chenodeoxycholate = beta-D-glucosyl-(1->3)-O-chenodeoxycholate + octan-1-ol

  Catalysed by SLCO1B1, SLCO1A2, SLCO1B3, GBA2extracellular space, cytosol

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

  Catalysed by SLC6A14, SLC26A6endoplasmic reticulum, cytosol, extracellular spaceOne of 8 routes

• 11-cis-retinyl hexadecanoateReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. 11-peroxy-docosahexaenoate to DHA conversion

  No catalyst recordedcytosol, extracellular spaceOne of 3 routes

• L-cystineReach from here →
  1. Arachidonate:oxygen 5-oxidoreductase
  2. Glutathione: 5-HPETE oxidoreductase
  3. cystine to cysteine conversion

  Catalysed by ALOX5, GPX5, GPX1, GPX2 and 6 morecytosolOne of 5 routes

• 11-cis-retinolReach from here →
  1. Arachidonate:CoA ligase (AMP-forming)
  2. Arachidonyl-CoA hydrolase
  3. Palmitoyl-CoA:retinol O-acyltransferase

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 14 morecytosolOne of 3 routes

• cob(II)alaminReach from here →
  1. (5Z,8Z,11Z,14Z)-eicosatetraenoate + AH2 + 2 O2 = prostaglandin H2 + A + H2O
  2. A + NADH + H(+) = AH2 + NAD(+)
  3. 2 cob(II)alamin + A + 2 H2O + 2 H(+) = 2 aquacob(III)alamin + AH2

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

• phosphatidic acidReach from here →
  1. Arachidonate:CoA ligase (AMP-forming)
  2. acyl-CoA pool formation and breakdown
  3. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 13 morecytosol, mitochondrial matrixOne of 7 routes

• (R)-carnitineReach from here →
  1. Utilized Transport
  2. solute carrier (L-carnitine)
  3. O-octanoyl-(R)-carnitine(in) + (R)-carnitine(out) = O-octanoyl-(R)-carnitine(out) + (R)-carnitine(in)

  Catalysed by SLC25A20endoplasmic reticulum, cytosol, mitochondrial matrix, inner side of the membrane, outer side of the membraneOne of 8 routes

• L-citrullineReach from here →
  1. transport of arachidonate and GSH (cytosol to extracellular)
  2. cystine to cysteine conversion
  3. transport of citrulline and cysteine (cytosol to extracellular)

  Catalysed by SLC7A6extracellular space, cytosolOne of 5 routes

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

  Catalysed by SLC6A14, SLC26A4endoplasmic reticulum, cytosol, extracellular spaceOne of 32 routes

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

  Catalysed by SLC6A14endoplasmic reticulum, cytosol, extracellular spaceOne of 14 routes

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

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

• nitric oxideReach from here →
  1. (5Z,8Z,11Z,14Z)-eicosatetraenoate + AH2 + 2 O2 = prostaglandin H2 + A + H2O
  2. A + NADH + H(+) = AH2 + NAD(+)
  3. 2 nitrite + AH2 + 2 H(+) = 2 nitric oxide + A + 2 H2O

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

• CHEBI:16523Reach 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. transport of D-serine and glycine (cytosol to extracellular)

  Catalysed by FAAH, PM20D1, SLC3A2, SLC7A10extracellular space, cytosolOne of 2 routes

• protein polypeptide chainReach from here →
  1. transport of arachidonate and GSH (cytosol to extracellular)
  2. cystine to cysteine conversion
  3. PROTEIN_BS

  No catalyst recordedextracellular space, cytosolOne of 3 routes

• 2-phenylacetamideReach 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:oxygen 2-oxidoreductase (decarboxylating)

  Catalysed by PM20D1, EPXcytosol