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

Three steps

• a 1-acylglycerone 3-phosphateReach from here →
  1. Arachidonate:CoA ligase (AMP-forming)
  2. acyl-CoA pool formation and breakdown
  3. dihydroxyacetone phosphate + an acyl-CoA = a 1-acylglycerone 3-phosphate + CoA

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

• (R)-2-hydroxyoctadecanoateReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. octadecanoate + 2 Fe(II)-[cytochrome b5] + O2 + 2 H(+) = (R)-2-hydroxyoctadecanoate + 2 Fe(III)-[cytochrome b5] + H2O

  Catalysed by FA2Hcytosol, extracellular space

• L-histidineReach from here →
  1. transport of arachidonate (cytosol to extracellular)
  2. transport of histamine (cytosol to extracellular)
  3. L-histidine + H(+) = histamine + CO2

  Catalysed by SLCO1B1, SLCO1A2, SLCO1B3, HDCextracellular space, cytosolOne of 3 routes

• sn-glycerol 3-phosphateReach 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 + ATP = sn-glycerol 3-phosphate + ADP + H(+)

  Catalysed by FAAH, CES2, ABHD16A, EPHX1 and 11 morecytosolOne of 2 routes

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

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 5 morecytosolOne of 2 routes

• an N-acylglycineReach from here →
  1. Arachidonate:CoA ligase (AMP-forming)
  2. acyl-CoA pool formation and breakdown
  3. an acyl-CoA + glycine = an N-acylglycine + CoA + H(+)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 7 morecytosolOne of 2 routes

• 2-oxo-3-sulfanylpropanoateReach from here →
  1. transport of arachidonate and GSH (cytosol to extracellular)
  2. cystine to cysteine conversion
  3. L-Cysteine:2-oxoglutarate aminotransferase

  Catalysed by GOT2, GOT1extracellular space, cytosolOne of 3 routes

• sn-glycerol 1-phosphateReach 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. sn-glycerol 1-phosphate + H2O = glycerol + phosphate

  Catalysed by FAAH, CES2, ABHD16A, EPHX1 and 8 morecytosol

• guanidinoacetateReach from here →
  1. Utilized Transport
  2. Carnitine Transport by Atb0
  3. Transport of Guanidinoacetic Acid

  Catalysed by SLC6A14endoplasmic reticulum, cytosol, extracellular spaceOne of 3 routes

• sphing-4-enineReach from here →
  1. Arachidonate:CoA ligase (AMP-forming)
  2. Arachidonyl-CoA hydrolase
  3. acyl-CoA:sphingosine N-acyltransferase

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 13 morecytosol, Golgi apparatusOne of 2 routes

• sphinganineReach 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 morecytosol

• spermidineReach from here →
  1. Arachidonate:CoA ligase (AMP-forming)
  2. Arachidonyl-CoA hydrolase
  3. diamine N-acetyltransferase (N1-acetylspermidine)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 11 morecytosolOne of 3 routes

• L-methionineReach from here →
  1. Arachidonate:CoA ligase (AMP-forming)
  2. Arachidonyl-CoA hydrolase
  3. N-acetylglutamate synthase (N-acetylmethionine)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 10 morecytosol, mitochondrial matrixOne of 26 routes

• a 1,2-diacyl-sn-glycero-3-phospho-(1D-myo-inositol)Reach from here →
  1. Arachidonate:CoA ligase (AMP-forming)
  2. acyl-CoA pool formation and breakdown
  3. a 1-acyl-sn-glycero-3-phospho-(1D-myo-inositol) + an acyl-CoA = a 1,2-diacyl-sn-glycero-3-phospho-(1D-myo-inositol) + CoA

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

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

  Catalysed by SLC6A14endoplasmic reticulum, cytosol, extracellular spaceOne of 17 routes

• glutathioneReach from here →
  1. Arachidonate:oxygen 5-oxidoreductase
  2. Glutathione: 5-HPETE oxidoreductase
  3. 2 glutathione + NADP(+) = glutathione disulfide + NADPH + H(+)

  Catalysed by ALOX5, GPX5, GPX1, GPX2 and 7 morecytosolOne of 17 routes

• L-kynurenineReach 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. Transport of L-Kynurenine

  Catalysed by PM20D1, SLC7A8extracellular space, cytosolOne of 2 routes

• beta-alanineReach from here →
  1. Utilized Transport
  2. Carnitine Transport by Atb0
  3. transport of beta-alanine and chloride (cytosol to extracellular)

  Catalysed by SLC6A14, SLC6A6endoplasmic reticulum, cytosol, extracellular spaceOne of 2 routes

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

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

• L-alanineReach from here →
  1. Arachidonate:CoA ligase (AMP-forming)
  2. Arachidonyl-CoA hydrolase
  3. amino-acid N-acetyltransferase (N-acetyl-L-alanine)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 9 morecytosol, mitochondrial matrixOne of 34 routes

• L-asparagineReach from here →
  1. Arachidonate:CoA ligase (AMP-forming)
  2. Arachidonyl-CoA hydrolase
  3. N-acetylglutamate synthase (N-acetyl-L-asparagine)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 10 morecytosol, mitochondrial matrixOne of 14 routes

• L,L-cystathionineReach from here →
  1. Arachidonate:CoA ligase (AMP-forming)
  2. Arachidonyl-CoA hydrolase
  3. N-acetylglutamate synthase (N-acetyl-L-cystathionine)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 10 morecytosol, mitochondrial matrixOne of 2 routes

• a 1-acyl-sn-glycero-3-phosphocholineReach from here →
  1. (5Z,8Z,11Z,14Z)-eicosatetraenoate + ATP + CoA = (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA + AMP + diphosphate
  2. (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA + a 1-acyl-sn-glycero-3-phosphocholine = 1-acyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholine + CoA
  3. 1-acyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholine + H2O = a 1-acyl-sn-glycero-3-phosphocholine + (5Z,8Z,11Z,14Z)-eicosatetraenoate + H(+)

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

• gamma-L-glutamyl-L-cysteineReach from here →
  1. transport of arachidonate and GSH (cytosol to extracellular)
  2. cystine to cysteine conversion
  3. L-glutamate:L-cysteine gamma-ligase (ADP-forming)

  Catalysed by GCLC, GCLMextracellular space, cytosolOne of 2 routes

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

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

• L-tyrosineReach 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, PAHOne of 2 routes

• 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

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

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

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

  Catalysed by CARS2extracellular space, cytosol

• N(tau)-methylhistamineReach from here →
  1. transport of arachidonate (cytosol to extracellular)
  2. transport of histamine (cytosol to extracellular)
  3. S-Adenosyl-L-methionine:histamine N-tele-methyltransferase

  Catalysed by SLCO1B1, SLCO1A2, SLCO1B3, HNMTextracellular space, cytosolOne of 3 routes

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

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 17 morecytosol

• (25R)-3alpha,7alpha,12alpha-trihydroxy-5beta-cholestan-26-oyl-CoAReach from here →
  1. Arachidonate:CoA ligase (AMP-forming)
  2. Arachidonyl-CoA hydrolase
  3. 3alpha,7alpha,12alpha-trihydroxy-5beta-cholestanoate:CoA ligase (AMP-forming)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 10 morecytosol, endoplasmic reticulumOne of 3 routes

• phosphoenolpyruvateReach from here →
  1. (5Z,8Z,11Z,14Z)-eicosatetraenoate + AH2 + 2 O2 = prostaglandin H2 + A + H2O
  2. (R)-malate + A = oxaloacetate + AH2
  3. oxaloacetate + GTP = phosphoenolpyruvate + GDP + CO2

  Catalysed by PTGS1, PTGS2, D2HGDH, PCK1 and 1 more

• deoxycholoyl-CoAReach from here →
  1. Arachidonate:CoA ligase (AMP-forming)
  2. Arachidonyl-CoA hydrolase
  3. cholate-CoA ligase (3alpha,12alpha-dihydroxy-5beta-cholanate)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 10 morecytosolOne of 4 routes

• hyodeoxycholateReach from here →
  1. transport of arachidonate (cytosol to extracellular)
  2. transport of lithocholate (cytosol to extracellular)
  3. cytochrome P450 (lithocholate)

  Catalysed by SLCO1B1, SLCO1A2, SLCO1B3, CYP3A4extracellular space, cytosol

• N-[(R)-4-phosphopantothenoyl]-L-cysteineReach from here →
  1. transport of arachidonate and GSH (cytosol to extracellular)
  2. cystine to cysteine conversion
  3. (R)-4'-phosphopantothenate:L-cysteine ligase

  Catalysed by PPCSextracellular space, cytosolOne of 4 routes

• 4-aminobutanoateReach from here →
  1. Utilized Transport
  2. Carnitine Transport by Atb0
  3. transport of 4-aminobutyrate and chloride (cytosol to extracellular)

  Catalysed by SLC6A14, SLC6A12endoplasmic reticulum, cytosol, extracellular spaceOne of 4 routes

• (2S)-2-phospholactateReach from here →
  1. prostaglandin-endoperoxide synthase (arachidonate)
  2. prostaglandin H2(out) + 2 (S)-lactate(in) = prostaglandin H2(in) + 2 (S)-lactate(out)
  3. (2S)-2-phospholactate + H2O = (S)-lactate + phosphate

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

• N-benzoylglycineReach 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. Hippurate (Benzoylglycinate) Formation

  Catalysed by FAAH, PM20D1mitochondrial matrixOne of 2 routes

• (9S)-hydroperoxy-(10E,12Z)-octadecadienoateReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. linoleate:oxygen 9-oxidoreductase

  No catalyst recordedcytosol, extracellular space

• 3-sulfino-L-alanineReach from here →
  1. transport of arachidonate and GSH (cytosol to extracellular)
  2. cystine to cysteine conversion
  3. L-Cysteine:oxygen oxidoreductase

  Catalysed by CDO1extracellular space, cytosolOne of 2 routes

• decanoyl-CoAReach from here →
  1. Arachidonate:CoA ligase (AMP-forming)
  2. Arachidonyl-CoA hydrolase
  3. medium-chain acyl-CoA ligase (decanoic acid)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 15 morecytosolOne of 7 routes

• (2E)-hexadecenoyl-CoAReach from here →
  1. Arachidonate:CoA ligase (AMP-forming)
  2. Arachidonyl-CoA hydrolase
  3. Carnitine O-Palmitoyltransferase

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 12 morecytosolOne of 6 routes

• (9Z)-hexadecenoyl-CoAReach from here →
  1. Arachidonate:CoA ligase (AMP-forming)
  2. Arachidonyl-CoA hydrolase
  3. long-chain-fatty-acid-CoA ligase (palmitolate)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 9 morecytosolOne of 17 routes

• a cardiolipinReach from here →
  1. Arachidonate:CoA ligase (AMP-forming)
  2. acyl-CoA pool formation and breakdown
  3. 1'-[1,2-diacyl-sn-glycero-3-phospho],3'-[1-acyl-sn-glycero-3-phospho]-glycerol + an acyl-CoA = a cardiolipin + CoA

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

• 3-hydroxyisovaleryl-CoAReach from here →
  1. Arachidonate:CoA ligase (AMP-forming)
  2. Arachidonyl-CoA hydrolase
  3. (3-Hydroxyisovalerylcoa->3-Hydroxyisovalerylcarnitine)

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

• chenodeoxycholoyl-CoAReach from here →
  1. transport of arachidonate (cytosol to extracellular)
  2. solute carrier organic anion transporter (chenodiol)
  3. chenodeoxycholate + ATP + CoA = chenodeoxycholoyl-CoA + AMP + diphosphate

  Catalysed by SLCO1B1, SLCO1A2, SLCO1B3, SLC27A5extracellular space, cytosol

• leukotriene D4Reach from here →
  1. transport of arachidonate (cytosol to extracellular)
  2. transport of leukotriene C4 (cytosol to extracellular)
  3. leukotriene C4 + H2O = leukotriene D4 + L-glutamate

  Catalysed by SLCO1B1, GGT1, GGT5extracellular space, cytosol

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

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 8 morecytosolOne of 5 routes

• a 1-acyl-sn-glycero-3-phosphoethanolamineReach from here →
  1. (5Z,8Z,11Z,14Z)-eicosatetraenoate + ATP + CoA = (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA + AMP + diphosphate
  2. a 1-acyl-sn-glycero-3-phosphoethanolamine + (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA = 1-acyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphoethanolamine + CoA
  3. 1-acyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphoethanolamine + H2O = a 1-acyl-sn-glycero-3-phosphoethanolamine + (5Z,8Z,11Z,14Z)-eicosatetraenoate + H(+)

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