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

Three steps

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

  Catalysed by SLCO1B1, SLCO1A2, SLCO1B3, SULT2A1extracellular space, cytosol

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

  Catalysed by SLCO1B1, SLCO1A2, SLCO1B3, SULT2A1extracellular space, cytosol

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

  Catalysed by SLCO1B1, SLCO1A2, SLCO1B3, SULT2A1extracellular space, cytosol

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

  Catalysed by SLCO1B1, SLCO1A2, SLCO1B3, SULT2A1extracellular space, cytosol

• deoxycholateReach from here →
  1. transport of arachidonate (cytosol to extracellular)
  2. solute carrier organic anion transporter (cholate)
  3. cytochrome P450 (cholate)

  Catalysed by SLCO1B1, SLCO1A2, SLCO1B3, CYP7A1extracellular space, cytosolOne of 4 routes

• CHEBI:240943Reach from here →
  1. Utilized Transport
  2. Carnitine Transport by Atb0
  3. 2-Methylbutyrylglycine Transport, Extracellular

  Catalysed by SLC6A14, SLC6A5endoplasmic reticulum, cytosol, extracellular spaceOne of 3 routes

• hypochlorous acidReach from here →
  1. Utilized Transport
  2. Carnitine Transport by Atb0
  3. Peroxidase

  Catalysed by SLC6A14, LPOendoplasmic reticulum, cytosol, extracellular spaceOne of 4 routes

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

  Catalysed by SLC6A14, SLC12A2, SLC12A1endoplasmic reticulum, cytosol, extracellular spaceOne of 3 routes

• imidazole-4-acetaldehydeReach from here →
  1. transport of arachidonate (cytosol to extracellular)
  2. transport of histamine (cytosol to extracellular)
  3. amine oxidase copper containing (histamine)

  Catalysed by SLCO1B1, SLCO1A2, SLCO1B3, AOC2 and 2 moreextracellular space, cytosolOne of 2 routes

• folic acidReach from here →
  1. (5Z,8Z,11Z,14Z)-eicosatetraenoate + AH2 + 2 O2 = prostaglandin H2 + A + H2O
  2. uridine(34) in tRNA + 5,10-methylenetetrahydrofolate + taurine + GTP + A + H2O = 5-taurinomethyluridine(34) in tRNA + 7,8-dihydrofolate + GDP + AH2 + phosphate + H(+)
  3. dihydrofolate:NAD+ oxidoreductase

  Catalysed by PTGS1, PTGS2, MTO1, DHFR and 1 morecytosolOne of 2 routes

• phenylacetylglycineReach 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. phenylacetyl-CoA:glycine N-phenylacetyltransferase

  Catalysed by FAAH, PM20D1, GLYATcytosolOne of 3 routes

• CHEBI:27540Reach from here →
  1. Arachidonate:CoA ligase (AMP-forming)
  2. Arachidonyl-CoA hydrolase
  3. medium-chain acyl-CoA ligase (hexanoic acid)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 15 morecytosolOne of 6 routes

• dodecanalReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. 2 H+[r] + lauric acid[r] + NADH[r] = H2O[r] + NAD+[r] + dodecanal[r]

  Catalysed by ALDH3A2cytosol, extracellular space, endoplasmic reticulumOne of 3 routes

• L-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(+) = L-glyceraldehyde + NADPH + H(+)

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

• 3,4-dihydroxyphenylacetaldehydeReach from here →
  1. transport of arachidonate (cytosol to extracellular)
  2. transport of dopamine (cytosol to extracellular)
  3. monoamine oxidase (dopamine)

  Catalysed by SLCO1B1, SLCO1A2, SLCO1B3, AOC2 and 4 moreextracellular space, cytosolOne of 2 routes

• 3beta-hydroxyandrost-5-en-17-oneReach from here →
  1. transport of arachidonate (cytosol to extracellular)
  2. transport of dehydroepiandrosterone sulfate (cytosol to extracellular)
  3. 3beta-Hydroxyandrost-5-en-17-one 3-sulfate sulfohydrolase

  Catalysed by SLCO1B1, STSextracellular space, cytosolOne of 3 routes

• CHEBI:28701Reach from here →
  1. Arachidonate:CoA ligase (AMP-forming)
  2. Arachidonyl-CoA hydrolase
  3. Propanoyl-CoA:acetyl-CoA C-acyltransferase

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 12 morecytosol, peroxisomeOne of 10 routes

• a fatty acidReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. N-acylsphingosine amidohydrolase
  3. an N-acylsphinganine + H2O = sphinganine + a fatty acid

  Catalysed by ASAH1, ACER2, ACER1, ASAH2 and 1 morecytosolOne of 4 routes

• CHEBI:28918Reach from here →
  1. transport of arachidonate (cytosol to extracellular)
  2. transport of noradrenaline (cytosol to extracellular)
  3. S-Adenosyl-L-methionine:phenylethanolamine N-methyltransferase

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

• N-acetyl-L-cysteineReach from here →
  1. transport of arachidonate and GSH (cytosol to extracellular)
  2. cystine to cysteine conversion
  3. N-acetylglutamate synthase (N-acetyl-L-cysteine)

  Catalysed by NAGSextracellular space, cytosol, mitochondrial matrix

• a dicarboxylateReach from here →
  1. transport of arachidonate (cytosol to extracellular)
  2. transport of prostaglandin E2 (cytosol to extracellular)
  3. prostaglandin E2(out) + a dicarboxylate(in) = prostaglandin E2(in) + a dicarboxylate(out)

  Catalysed by SLCO1B1, SLCO1A2, SLCO1B3, SLC22A6extracellular space, cytosol, inner side of the membrane, outer side of the membraneOne of 4 routes

• iron(2+)Reach from here →
  1. transport of arachidonate and GSH (cytosol to extracellular)
  2. glutathione:dehydroascorbate oxidoreductase
  3. cytochrome b reductase (ascorbate)

  Catalysed by CYBRD1extracellular space, cytosol

• Cu(2+)Reach 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. Cu(2+)(out) + L-ascorbate(in) = Cu(+)(out) + monodehydro-L-ascorbate radical(in) + H(+)

  Catalysed by CYBRD1cytosol, inner side of the membrane, outer side of the membrane

• L-ascorbic 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. a [peptide]-C-terminal glycine + 2 L-ascorbate + O2 = a [peptide]-C-terminal (2S)-2-hydroxyglycine + 2 monodehydro-L-ascorbate radical + H2O

  Catalysed by PAMcytosolOne of 9 routes

• K(+)Reach from here →
  1. transport of arachidonate (cytosol to extracellular)
  2. transport of serotonin (cytosol to extracellular)
  3. serotonin(out) + K(+)(in) + Na(+)(out) + H(+)(in) = serotonin(in) + K(+)(out) + Na(+)(in) + H(+)(out)

  Catalysed by SLCO1B1, SLCO1A2, SLCO1B3, SLC6A4extracellular space, cytosol, inner side of the membrane, outer side of the membraneOne of 3 routes

• Cys-tRNA(Cys)Reach from here →
  1. transport of arachidonate and GSH (cytosol to extracellular)
  2. cystine to cysteine conversion
  3. L-Cysteine:tRNA(Cys) ligase (AMP-forming)

  Catalysed by CARS1extracellular space, cytosol

• Phe-tRNA(Phe)Reach 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:tRNA(Ala) ligase (AMP-forming)

  Catalysed by PM20D1, FARSB, FARSAcytosol

• Gly-tRNA(Gly)Reach 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:tRNA(Gly) ligase (AMP-forming)

  Catalysed by FAAH, PM20D1, GARS1cytosol

• hydrogenselenideReach from here →
  1. (5Z,8Z,11Z,14Z)-eicosatetraenoate + AH2 + 2 O2 = prostaglandin H2 + A + H2O
  2. A + NADH + H(+) = AH2 + NAD(+)
  3. L-selenocysteine + AH2 = hydrogenselenide + L-alanine + A + H(+)

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

• hydrogen sulfideReach 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 2 routes

• L-aspartateReach from here →
  1. (5Z,8Z,11Z,14Z)-eicosatetraenoate + AH2 + 2 O2 = prostaglandin H2 + A + H2O
  2. (R)-malate + A = oxaloacetate + AH2
  3. L-Aspartate:2-oxoglutarate aminotransferase

  Catalysed by PTGS1, PTGS2, D2HGDH, GOT2mitochondrial matrixOne of 7 routes

• acetateReach from here →
  1. transport of arachidonate (cytosol to extracellular)
  2. transport of acetylcholine (cytosol to extracellular)
  3. Acetylcholine aectylhydrolase

  Catalysed by SLCO1B1, SLCO1B3, BCHE, ACHEextracellular space, cytosolOne of 3 routes

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

  Catalysed by SLC6A14, SLC26A4endoplasmic reticulum, cytosol, extracellular spaceOne of 3 routes

• propionic acidReach from here →
  1. Utilized Transport
  2. Active Transport
  3. Propanoyl-CoA hydrolase

  Catalysed by ACOT7endoplasmic reticulum, cytosol, mitochondrial matrixOne of 3 routes

• citric acidReach from here →
  1. (5Z,8Z,11Z,14Z)-eicosatetraenoate + AH2 + 2 O2 = prostaglandin H2 + A + H2O
  2. (R)-malate + A = oxaloacetate + AH2
  3. acetyl-CoA:oxaloacetate C-acetyltransferase (thioester-hydrolysing)

  Catalysed by PTGS1, PTGS2, D2HGDH, CSmitochondrial matrixOne of 2 routes

• butyric acidReach from here →
  1. Utilized Transport
  2. transport of butyryl-CoA and L-carnitine (cytosol to mitochondria)
  3. Butyryl-CoA hydrolase

  Catalysed by SLC33A1, ESCO2, OXSM, ACOT12endoplasmic reticulum, cytosol, mitochondrial matrix

• malonic acidReach from here →
  1. Utilized Transport
  2. Carnitine Transport by Atb0
  3. Malonate Transport, Antiport with Chloride

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

• glutarateReach from here →
  1. transport of arachidonate (cytosol to extracellular)
  2. solute carrier organic anion transporter (glycocholate)
  3. glycocholate(out) + glutarate(in) = glycocholate(in) + glutarate(out)

  Catalysed by SLCO1B1, SLCO1A2, SLCO1B3, SLC22A24extracellular space, cytosol, inner side of the membrane, outer side of the membraneOne of 12 routes

• 4-hydroxy-2-oxoglutaric acidReach from here →
  1. (5Z,8Z,11Z,14Z)-eicosatetraenoate + AH2 + 2 O2 = prostaglandin H2 + A + H2O
  2. (R)-malate + A = oxaloacetate + AH2
  3. D-aspartate:2-oxoglutarate aminotransferase

  Catalysed by PTGS1, PTGS2, D2HGDH, GOT2mitochondrial matrix

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

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

• an N-acyl-(4R)-4-hydroxysphinganineReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. N-acylsphingosine amidohydrolase
  3. dihydroceramide,ferrocytochrome b5:oxygen oxidoreductase (C4-hydroxylating)

  Catalysed by ASAH1, ACER2, ACER1, ASAH2 and 3 morecytosolOne of 2 routes

• 3-oxopropanoateReach from here →
  1. prostaglandin-endoperoxide synthase (arachidonate)
  2. thromboxane A synthase (12(S)-HHT)
  3. malonaldehyde + NAD(+) + H2O = 3-oxopropanoate + NADH + 2 H(+)

  Catalysed by PTGS1, PTGS2, TBXAS1, ALDH1A1 and 2 morecytosol

• methylarsonateReach from here →
  1. Arachidonate:oxygen 5-oxidoreductase
  2. Glutathione: 5-HPETE oxidoreductase
  3. methylarsonate + 2 glutathione + H(+) = methylarsonous acid + glutathione disulfide + H2O

  Catalysed by ALOX5, GPX5, GPX1, GPX2 and 8 morecytosol

• thiosulfateReach from here →
  1. Arachidonate:oxygen 5-oxidoreductase
  2. Glutathione: 5-HPETE oxidoreductase
  3. thiosulfate + 2 glutathione = glutathione disulfide + hydrogen sulfide + sulfite + 2 H(+)

  Catalysed by ALOX5, GPX5, GPX1, GPX2 and 7 morecytosolOne of 2 routes

• di-mu-sulfido-diiron(2+)Reach from here →
  1. transport of arachidonate and GSH (cytosol to extracellular)
  2. cystine to cysteine conversion
  3. De novo synthesis of 2Fe2S

  Catalysed by NDUFAB1, FDXR, FXN, FDX2 and 3 moreextracellular space, cytosol, mitochondrial matrix

• 1-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycerolReach from here →
  1. Arachidonate:CoA ligase (AMP-forming)
  2. glycerol-3-phosphate 1-O-acyltransferase (arachidonyl-CoA)
  3. 1-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphate + H2O = 1-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycerol + phosphate

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

• 5-aminolevulinateReach 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 + H(+) = 5-aminolevulinate + CO2 + CoA

  Catalysed by FAAH, PM20D1, ALAS1, ALAS2

• 12-hydroxydodecanoateReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. alkane 1-monooxygenase (lauric acid)

  Catalysed by CYP4A11, CYP4A22cytosol, extracellular spaceOne of 2 routes

• glycochenodeoxycholateReach 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. chenodeoxycholoyl-CoA + glycine = glycochenodeoxycholate + CoA + H(+)

  Catalysed by FAAH, PM20D1, BAAT

• glycochenodeoxycholic 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. bile acid-CoA: amino acid N-acyltransferase

  Catalysed by FAAH, PM20D1, BAATperoxisomeOne of 3 routes