all-cis-docosa-4,7,10,13,16,19-hexaenoic acid

Three steps

• 1-hexadecanoyl-sn-glycero-3-phosphateReach from here →
  1. 11-peroxy-docosahexaenoate to DHA conversion
  2. Palmitoyl-CoA:retinol O-acyltransferase
  3. glycerol-3-phosphate 1-O-acyltransferase (palmitoyl-CoA)

  Catalysed by DGAT1, LRAT, AWAT1, AWAT2 and 5 morecytosol

• a 1-acylglycerone 3-phosphateReach from here →
  1. long-chain-fatty-acid-CoA ligase (DHA)
  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

• a 1,2-diacyl-sn-glycero-3-phosphocholineReach from here →
  1. long-chain-fatty-acid-CoA ligase (DHA)
  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. long-chain-fatty-acid-CoA ligase (DHA)
  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 morecytosol

• 2-oxo-3-sulfanylpropanoateReach from here →
  1. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoate + AH2 + O2 = 17R-hydroxy-(4Z,7Z,10Z,13Z,15E,19Z)-docosahexaenoate + A + H2O
  2. Mo-molybdopterin + L-cysteine + AH2 = thio-Mo-molybdopterin + L-alanine + A + H2O
  3. L-Cysteine:2-oxoglutarate aminotransferase

  Catalysed by PTGS2, MOCOS, GOT2, GOT1cytosolOne of 3 routes

• S-formylglutathioneReach from here →
  1. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoate + AH2 + O2 = 17R-hydroxy-(4Z,7Z,10Z,13Z,15E,19Z)-docosahexaenoate + 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. alcohol dehydrogenase (formaldehyde)

  Catalysed by PTGS2, KDM1A, KDM1B, ADH1C and 5 morecytosol

• sphing-4-enineReach from here →
  1. long-chain-fatty-acid-CoA ligase (DHA)
  2. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoyl-CoA hydrolase
  3. acyl-CoA:sphingosine N-acyltransferase

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 10 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. long-chain-fatty-acid-CoA ligase (DHA)
  2. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoyl-CoA hydrolase
  3. diamine N-acetyltransferase (N1-acetylspermidine)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 8 morecytosolOne of 3 routes

• L-methionineReach from here →
  1. long-chain-fatty-acid-CoA ligase (DHA)
  2. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoyl-CoA hydrolase
  3. N-acetylglutamate synthase (N-acetylmethionine)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 7 morecytosol, mitochondrial matrixOne of 11 routes

• a 1,2-diacyl-sn-glycero-3-phospho-(1D-myo-inositol)Reach from here →
  1. long-chain-fatty-acid-CoA ligase (DHA)
  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. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoate + AH2 + O2 = 17R-hydroxy-(4Z,7Z,10Z,13Z,15E,19Z)-docosahexaenoate + A + H2O
  2. Mo-molybdopterin + L-cysteine + AH2 = thio-Mo-molybdopterin + L-alanine + A + H2O
  3. transport of cysteine and tryptophan (cytosol to extracellular)

  Catalysed by PTGS2, MOCOS, SLC7A5extracellular space, cytosolOne of 4 routes

• glutathioneReach from here →
  1. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoate + O2 = (17S)-hydroperoxy-(4Z,7Z,10Z,13Z,15E,19Z)-docosahexaenoate
  2. (17S)-hydroperoxy-(4Z,7Z,10Z,13Z,15E,19Z)-docosahexaenoate + 2 glutathione = (17S)-hydroxy-(4Z,7Z,10Z,13Z,15E,19Z)-docosahexaenoate + glutathione disulfide + H2O
  3. 2 glutathione + NADP(+) = glutathione disulfide + NADPH + H(+)

  Catalysed by ALOX5, ALOX15, GPX1, GPX4 and 1 moreOne of 4 routes

• a 1-acyl-sn-glycero-3-phosphateReach from here →
  1. long-chain-fatty-acid-CoA ligase (DHA)
  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. long-chain-fatty-acid-CoA ligase (DHA)
  2. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoyl-CoA hydrolase
  3. amino-acid N-acetyltransferase (N-acetyl-L-alanine)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 6 morecytosol, mitochondrial matrixOne of 18 routes

• L-asparagineReach from here →
  1. long-chain-fatty-acid-CoA ligase (DHA)
  2. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoyl-CoA hydrolase
  3. N-acetylglutamate synthase (N-acetyl-L-asparagine)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 7 morecytosol, mitochondrial matrixOne of 5 routes

• L-phenylalanineReach from here →
  1. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoate + AH2 + O2 = 17R-hydroxy-(4Z,7Z,10Z,13Z,15E,19Z)-docosahexaenoate + A + H2O
  2. Mo-molybdopterin + L-cysteine + AH2 = thio-Mo-molybdopterin + L-alanine + A + H2O
  3. transport of cysteine and phenylalanine (cytosol to extracellular)

  Catalysed by PTGS2, MOCOS, SLC7A5extracellular space, cytosolOne of 6 routes

• L,L-cystathionineReach from here →
  1. long-chain-fatty-acid-CoA ligase (DHA)
  2. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoyl-CoA hydrolase
  3. N-acetylglutamate synthase (N-acetyl-L-cystathionine)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 7 morecytosol, mitochondrial matrix

• gamma-L-glutamyl-L-cysteineReach from here →
  1. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoate + AH2 + O2 = 17R-hydroxy-(4Z,7Z,10Z,13Z,15E,19Z)-docosahexaenoate + A + H2O
  2. Mo-molybdopterin + L-cysteine + AH2 = thio-Mo-molybdopterin + L-alanine + A + H2O
  3. L-glutamate:L-cysteine gamma-ligase (ADP-forming)

  Catalysed by PTGS2, MOCOS, GCLC, GCLMcytosolOne of 2 routes

• 3-oxosphinganineReach from here →
  1. 11-peroxy-docosahexaenoate to DHA conversion
  2. Palmitoyl-CoA:retinol O-acyltransferase
  3. Palmitoyl-CoA:L-serine C-palmitoyltransferase (decarboxylating)

  Catalysed by DGAT1, LRAT, AWAT1, AWAT2 and 4 morecytosol

• 1-hexadecanoylglycerone 3-phosphateReach from here →
  1. 11-peroxy-docosahexaenoate to DHA conversion
  2. Palmitoyl-CoA:retinol O-acyltransferase
  3. glyceronephosphate O-acyltransferase (DHAP)

  Catalysed by DGAT1, LRAT, AWAT1, AWAT2 and 2 morecytosol, peroxisome

• (3Z)-dodecenoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (DHA)
  2. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoyl-CoA hydrolase
  3. acetyl-CoA C-acyltransferase (3-oxomyrist-5-enoyl-CoA)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 9 morecytosol, mitochondrial matrixOne of 3 routes

• S-sulfanyl-L-cysteineReach from here →
  1. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoate + AH2 + O2 = 17R-hydroxy-(4Z,7Z,10Z,13Z,15E,19Z)-docosahexaenoate + A + H2O
  2. Mo-molybdopterin + L-cysteine + AH2 = thio-Mo-molybdopterin + L-alanine + A + H2O
  3. 2 L-cysteine = S-sulfanyl-L-cysteine + L-alanine

  Catalysed by PTGS2, MOCOS, CARS2

• a 1,2-diacyl-sn-glycero-3-phosphateReach from here →
  1. long-chain-fatty-acid-CoA ligase (DHA)
  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. long-chain-fatty-acid-CoA ligase (DHA)
  2. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoyl-CoA hydrolase
  3. 3alpha,7alpha,12alpha-trihydroxy-5beta-cholestanoate:CoA ligase (AMP-forming)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 7 morecytosol, endoplasmic reticulumOne of 3 routes

• phosphoenolpyruvateReach from here →
  1. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoate + AH2 + O2 = 17R-hydroxy-(4Z,7Z,10Z,13Z,15E,19Z)-docosahexaenoate + A + H2O
  2. (R)-malate + A = oxaloacetate + AH2
  3. oxaloacetate + GTP = phosphoenolpyruvate + GDP + CO2

  Catalysed by PTGS2, D2HGDH, PCK1, PCK2

• deoxycholoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (DHA)
  2. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoyl-CoA hydrolase
  3. cholate-CoA ligase (3alpha,12alpha-dihydroxy-5beta-cholanate)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 7 morecytosolOne of 4 routes

• N-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-glycineReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. N-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-glycine + H2O = (5Z,8Z,11Z,14Z)-eicosatetraenoate + glycine

  Catalysed by FAAH, PM20D1cytosol, extracellular space

• N-[(R)-4-phosphopantothenoyl]-L-cysteineReach from here →
  1. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoate + AH2 + O2 = 17R-hydroxy-(4Z,7Z,10Z,13Z,15E,19Z)-docosahexaenoate + A + H2O
  2. Mo-molybdopterin + L-cysteine + AH2 = thio-Mo-molybdopterin + L-alanine + A + H2O
  3. (R)-4'-phosphopantothenate:L-cysteine ligase

  Catalysed by PTGS2, MOCOS, PPCScytosolOne of 4 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. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoate + AH2 + O2 = 17R-hydroxy-(4Z,7Z,10Z,13Z,15E,19Z)-docosahexaenoate + A + H2O
  2. Mo-molybdopterin + L-cysteine + AH2 = thio-Mo-molybdopterin + L-alanine + A + H2O
  3. L-Cysteine:oxygen oxidoreductase

  Catalysed by PTGS2, MOCOS, CDO1cytosolOne of 2 routes

• decanoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (DHA)
  2. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoyl-CoA hydrolase
  3. medium-chain acyl-CoA ligase (decanoic acid)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 12 morecytosolOne of 7 routes

• (2E)-hexadecenoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (DHA)
  2. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoyl-CoA hydrolase
  3. Carnitine O-Palmitoyltransferase

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

• (9Z)-hexadecenoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (DHA)
  2. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoyl-CoA hydrolase
  3. long-chain-fatty-acid-CoA ligase (palmitolate)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 6 morecytosolOne of 20 routes

• a cardiolipinReach from here →
  1. long-chain-fatty-acid-CoA ligase (DHA)
  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. long-chain-fatty-acid-CoA ligase (DHA)
  2. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoyl-CoA hydrolase
  3. (3-Hydroxyisovalerylcoa->3-Hydroxyisovalerylcarnitine)

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

• an all-trans-retinyl esterReach from here →
  1. long-chain-fatty-acid-CoA ligase (DHA)
  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 8 routes

• 18-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. cytochrome P450 (arachidonate)

  Catalysed by CYP4F8cytosol, extracellular space, endoplasmic reticulumOne of 2 routes

• a 1,2-diacyl-sn-glycero-3-phosphoethanolamineReach from here →
  1. long-chain-fatty-acid-CoA ligase (DHA)
  2. acyl-CoA pool formation and breakdown
  3. a 1-acyl-sn-glycero-3-phosphoethanolamine + an acyl-CoA = a 1,2-diacyl-sn-glycero-3-phosphoethanolamine + CoA

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

• a triacyl-sn-glycerolReach from here →
  1. long-chain-fatty-acid-CoA ligase (DHA)
  2. acyl-CoA pool formation and breakdown
  3. an acyl-CoA + a 1,2-diacyl-sn-glycerol = a triacyl-sn-glycerol + CoA

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

• a 1,2-diacyl-sn-glycero-3-phospho-(1'-sn-glycerol)Reach from here →
  1. long-chain-fatty-acid-CoA ligase (DHA)
  2. acyl-CoA pool formation and breakdown
  3. 1-acyl-sn-glycero-3-phospho-(1'-sn-glycerol) + an acyl-CoA = a 1,2-diacyl-sn-glycero-3-phospho-(1'-sn-glycerol) + CoA

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 7 morecytosol

• hexacosanoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (DHA)
  2. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoyl-CoA hydrolase
  3. long-chain-fatty-acid-CoA ligase (cerotic acid)

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

• tetracosanoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (DHA)
  2. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoyl-CoA hydrolase
  3. long-chain-fatty-acid-CoA ligase (lignocerate)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 6 morecytosolOne of 17 routes

• docosanoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (DHA)
  2. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoyl-CoA hydrolase
  3. long-chain-fatty-acid-CoA ligase (behenic acid)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 6 morecytosolOne of 14 routes

• a 2,3-saturated acyl-CoAReach from here →
  1. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoate + AH2 + O2 = 17R-hydroxy-(4Z,7Z,10Z,13Z,15E,19Z)-docosahexaenoate + A + H2O
  2. A + NADH + H(+) = AH2 + NAD(+)
  3. a 2,3-saturated acyl-CoA + A = a 2,3-dehydroacyl-CoA + AH2

  Catalysed by PTGS2, AIFM1, PYROXD1, ACAD10One of 2 routes

• an N-acylsphinganine-1-phosphocholineReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. N-acylsphingosine amidohydrolase
  3. an N-acylsphinganine + a 1,2-diacyl-sn-glycero-3-phosphocholine = an N-acylsphinganine-1-phosphocholine + a 1,2-diacyl-sn-glycerol

  Catalysed by ASAH1, ACER2, ACER1, ASAH2 and 3 morecytosol

• all-trans-retinyl 9Z-octadecenoateReach from here →
  1. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoate + AH2 + O2 = 17R-hydroxy-(4Z,7Z,10Z,13Z,15E,19Z)-docosahexaenoate + A + H2O
  2. all-trans-13,14-dihydroretinol + A = all-trans-retinol + AH2
  3. 1,2,3-tri-(9Z-octadecenoyl)-glycerol + all-trans-retinol = all-trans-retinyl 9Z-octadecenoate + di-(9Z)-octadecenoylglycerol

  Catalysed by PTGS2, RETSAT, PNPLA4, PNPLA2

• 3-oxooctadecanoyl-CoAReach from here →
  1. 11-peroxy-docosahexaenoate to DHA conversion
  2. Palmitoyl-CoA:retinol O-acyltransferase
  3. very-long-chain 3-oxoacyl-CoA synthase (malonyl-CoA)

  Catalysed by DGAT1, LRAT, AWAT1, AWAT2 and 8 morecytosolOne of 2 routes

• (2E)-octadecenoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (DHA)
  2. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoyl-CoA hydrolase
  3. Carnitine O-Palmitoyltransferase

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 9 morecytosolOne of 4 routes