11-cis-retinyl hexadecanoate

Three steps

• (2E)-tetradecenoyl-CoAReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. Fatty Acid Beta Oxidation (C16->C14), Mitochondrial
  3. trans-tetradec-2-enoyl-CoA reductase

  Catalysed by DGAT1, LRAT, AWAT1, AWAT2 and 5 morecytosol, mitochondrial matrixOne of 5 routes

• decanoyl-CoAReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. Palmitoyl-CoA:retinol O-acyltransferase
  3. medium-chain acyl-CoA ligase (decanoic acid)

  Catalysed by DGAT1, LRAT, AWAT1, AWAT2 and 7 morecytosolOne of 8 routes

• D-glucose 6-phosphateReach from here →
  1. 11-peroxy-docosahexaenoate to DHA conversion
  2. NAADPH + 2 O2 = NAADP(+) + 2 superoxide + H(+)
  3. NAADP(+) + D-glucose 6-phosphate = NAADPH + 6-phospho-D-glucono-1,5-lactone + H(+)

  Catalysed by NOX5, G6PDcytosol

• Fe(II)-heme aReach from here →
  1. 11-peroxy-docosahexaenoate to DHA conversion
  2. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoate + AH2 + O2 = 17R-hydroxy-(4Z,7Z,10Z,13Z,15E,19Z)-docosahexaenoate + A + H2O
  3. Fe(II)-heme o + 2 A + H2O = Fe(II)-heme a + 2 AH2

  Catalysed by PTGS2, COX15cytosol

• a cardiolipinReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  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 DGAT1, LRAT, AWAT1, AWAT2 and 2 morecytosol

• (2E)-octenoyl-CoAReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. Beta Oxidation of Long Chain Fatty Acid
  3. trans-oct-2-enoyl-CoA reductase

  Catalysed by DGAT1, LRAT, AWAT1, AWAT2 and 4 morecytosol, mitochondrial matrixOne of 5 routes

• 3-hydroxyisovaleryl-CoAReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. Palmitoyl-CoA:retinol O-acyltransferase
  3. (3-Hydroxyisovalerylcoa->3-Hydroxyisovalerylcarnitine)

  Catalysed by DGAT1, LRAT, AWAT1, AWAT2 and 3 morecytosol

• CHEBI:63544Reach from here →
  1. 11-peroxy-docosahexaenoate to DHA conversion
  2. long-chain-fatty-acid-CoA ligase (DHA)
  3. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoyl-CoA reduction

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

• a 1,2-diacyl-sn-glycero-3-phosphoethanolamineReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  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 DGAT1, LRAT, AWAT1, AWAT2 and 5 morecytosol

• a triacyl-sn-glycerolReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. acyl-CoA pool formation and breakdown
  3. an acyl-CoA + a 1,2-diacyl-sn-glycerol = a triacyl-sn-glycerol + CoA

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

• a 1,2-diacyl-sn-glycero-3-phospho-(1'-sn-glycerol)Reach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  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 DGAT1, LRAT, AWAT1, AWAT2 and 4 morecytosol

• 1-hexadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phosphateReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. glycerol-3-phosphate 1-O-acyltransferase (palmitoyl-CoA)
  3. 1-hexadecanoyl-sn-glycero-3-phosphate + (9Z)-octadecenoyl-CoA = 1-hexadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phosphate + CoA

  Catalysed by DGAT1, LRAT, AWAT1, AWAT2 and 13 morecytosol

• hexacosanoyl-CoAReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. Palmitoyl-CoA:retinol O-acyltransferase
  3. long-chain-fatty-acid-CoA ligase (cerotic acid)

  Catalysed by DGAT1, LRAT, AWAT1, AWAT2 and 9 morecytosolOne of 6 routes

• tetracosanoyl-CoAReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. Palmitoyl-CoA:retinol O-acyltransferase
  3. long-chain-fatty-acid-CoA ligase (lignocerate)

  Catalysed by DGAT1, LRAT, AWAT1, AWAT2 and 9 morecytosolOne of 11 routes

• 1-octadecanoyl-2-acyl-sn-glycero-3-phospho-1D-myo-inositolReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. fatty-acyl-CoA synthase (N-C18:0CoA)
  3. a 2-acyl-sn-glycero-3-phospho-D-myo-inositol + octadecanoyl-CoA = 1-octadecanoyl-2-acyl-sn-glycero-3-phospho-1D-myo-inositol + CoA

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

• docosanoyl-CoAReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. Palmitoyl-CoA:retinol O-acyltransferase
  3. long-chain-fatty-acid-CoA ligase (behenic acid)

  Catalysed by DGAT1, LRAT, AWAT1, AWAT2 and 9 morecytosolOne of 10 routes

• 3-oxoeicosasphinganineReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. fatty-acyl-CoA synthase (N-C18:0CoA)
  3. octadecanoyl-CoA + L-serine + H(+) = 3-oxoeicosasphinganine + CO2 + CoA

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

• 3-oxoeicosanoyl-CoAReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. fatty-acyl-CoA synthase (N-C18:0CoA)
  3. very-long-chain 3-oxoacyl-CoA synthase (malonyl-CoA)

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

• N-(octadecanoyl)-sphinganineReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. fatty-acyl-CoA synthase (N-C18:0CoA)
  3. sphinganine + octadecanoyl-CoA = N-(octadecanoyl)-sphinganine + CoA + H(+)

  Catalysed by DGAT1, LRAT, AWAT1, AWAT2 and 7 morecytosol

• N-(tetradecanoyl)-sphinganineReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. Fatty Acid Beta Oxidation (C16->C14), Mitochondrial
  3. sphinganine + tetradecanoyl-CoA = N-(tetradecanoyl)-sphinganine + CoA + H(+)

  Catalysed by DGAT1, LRAT, AWAT1, AWAT2 and 6 morecytosol, mitochondrial matrix

• all-trans-retinyl 9Z-octadecenoateReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. all-trans-Retinol 11-cis-trans-isomerase
  3. 1,2,3-tri-(9Z-octadecenoyl)-glycerol + all-trans-retinol = all-trans-retinyl 9Z-octadecenoate + di-(9Z)-octadecenoylglycerol

  Catalysed by DGAT1, LRAT, AWAT1, AWAT2 and 3 morecytosol

• 3-oxohexadecasphinganineReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. Fatty Acid Beta Oxidation (C16->C14), Mitochondrial
  3. tetradecanoyl-CoA + L-serine + H(+) = 3-oxohexadecasphinganine + CO2 + CoA

  Catalysed by DGAT1, LRAT, AWAT1, AWAT2 and 6 morecytosol, mitochondrial matrix

• Mo-molybdopterinReach from here →
  1. 11-peroxy-docosahexaenoate to DHA conversion
  2. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoate + AH2 + O2 = 17R-hydroxy-(4Z,7Z,10Z,13Z,15E,19Z)-docosahexaenoate + A + H2O
  3. Mo-molybdopterin + L-cysteine + AH2 = thio-Mo-molybdopterin + L-alanine + A + H2O

  Catalysed by PTGS2, MOCOScytosol

• (2E)-octadecenoyl-CoAReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. Palmitoyl-CoA:retinol O-acyltransferase
  3. Carnitine O-Palmitoyltransferase

  Catalysed by DGAT1, LRAT, AWAT1, AWAT2 and 4 morecytosolOne of 9 routes

• (6Z,9Z,12Z,15Z)-octadecatetraenoyl-CoAReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. Palmitoyl-CoA:retinol O-acyltransferase
  3. long-chain-fatty-acid-CoA ligase (stearidonic acid)

  Catalysed by DGAT1, LRAT, AWAT1, AWAT2 and 9 morecytosolOne of 9 routes

• (8Z,11Z,14Z)-eicosatrienoateReach from here →
  1. 11-peroxy-docosahexaenoate to DHA conversion
  2. (10Z)-heptadecenoic acid formation
  3. (10Z)-heptadecenoic acid formation

  No catalyst recordedcytosol, extracellular spaceOne of 12 routes

• 1-tetradecanoyl-sn-glycerol 3-phosphateReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. Fatty Acid Beta Oxidation (C16->C14), Mitochondrial
  3. glycerol-3-phosphate 1-O-acyltransferase (myristoyl-CoA)

  Catalysed by DGAT1, LRAT, AWAT1, AWAT2 and 8 morecytosol, mitochondrial matrix

• 1-hexadecanoyl-2-octadecanoyl-sn-glycero-3-phospho-(1D-myo-inositol)Reach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. fatty-acyl-CoA synthase (N-C18:0CoA)
  3. 1-hexadecanoyl-sn-glycero-3-phospho-(1D-myo-inositol) + octadecanoyl-CoA = 1-hexadecanoyl-2-octadecanoyl-sn-glycero-3-phospho-(1D-myo-inositol) + CoA

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

• 1-hexadecanoyl-2-octadecanoyl-sn-glycero-3-phospho-(1'-sn-glycerol)Reach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. fatty-acyl-CoA synthase (N-C18:0CoA)
  3. 1-hexadecanoyl-sn-glycero-3-phospho-(1'-sn-glycerol) + octadecanoyl-CoA = 1-hexadecanoyl-2-octadecanoyl-sn-glycero-3-phospho-(1'-sn-glycerol) + CoA

  Catalysed by DGAT1, LRAT, AWAT1, AWAT2 and 3 morecytosol

• 1-hexadecanoyl-2-octadecanoyl-sn-glycero-3-phosphateReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. glycerol-3-phosphate 1-O-acyltransferase (palmitoyl-CoA)
  3. 1-hexadecanoyl-sn-glycero-3-phosphate + octadecanoyl-CoA = 1-hexadecanoyl-2-octadecanoyl-sn-glycero-3-phosphate + CoA

  Catalysed by DGAT1, LRAT, AWAT1, AWAT2 and 6 morecytosolOne of 2 routes

• 1-hexadecanoyl-2-tetradecanoyl-sn-glycero-3-phosphateReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. glycerol-3-phosphate 1-O-acyltransferase (palmitoyl-CoA)
  3. 1-hexadecanoyl-sn-glycero-3-phosphate + tetradecanoyl-CoA = 1-hexadecanoyl-2-tetradecanoyl-sn-glycero-3-phosphate + CoA

  Catalysed by DGAT1, LRAT, AWAT1, AWAT2 and 6 morecytosolOne of 2 routes

• 1,2-dihexadecanoyl-sn-glycero-3-phosphateReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. glycerol-3-phosphate 1-O-acyltransferase (palmitoyl-CoA)
  3. 1-hexadecanoyl-sn-glycero-3-phosphate + hexadecanoyl-CoA = 1,2-dihexadecanoyl-sn-glycero-3-phosphate + CoA

  Catalysed by DGAT1, LRAT, AWAT1, AWAT2 and 6 morecytosol

• 1-hexadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphateReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. glycerol-3-phosphate 1-O-acyltransferase (palmitoyl-CoA)
  3. 1-hexadecanoyl-sn-glycero-3-phosphate + (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA = 1-hexadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphate + CoA

  Catalysed by DGAT1, LRAT, AWAT1, AWAT2 and 7 morecytosol

• N-octadecanoylsphing-4-enineReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. fatty-acyl-CoA synthase (N-C18:0CoA)
  3. sphing-4-enine + octadecanoyl-CoA = N-octadecanoylsphing-4-enine + CoA + H(+)

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

• 1-hexadecanoyl-2-octadecanoyl-sn-glycero-3-phosphocholineReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. fatty-acyl-CoA synthase (N-C18:0CoA)
  3. octadecanoyl-CoA + 1-hexadecanoyl-sn-glycero-3-phosphocholine = 1-hexadecanoyl-2-octadecanoyl-sn-glycero-3-phosphocholine + CoA

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

• (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoAReach from here →
  1. 11-peroxy-docosahexaenoate to DHA conversion
  2. long-chain-fatty-acid-CoA ligase (DHA)
  3. Beta Oxidation of Long Chain Fatty Acid

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

• (7Z,10Z,13Z,16Z,19Z)-docosapentaenoyl-CoAReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. Palmitoyl-CoA:retinol O-acyltransferase
  3. long-chain-fatty-acid-CoA ligase (DPA)

  Catalysed by DGAT1, LRAT, AWAT1, AWAT2 and 9 morecytosolOne of 7 routes

• 1-hexadecanoyl-2-[(9Z)-hexadec-9-enoyl]-sn-glycero-3-phosphateReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. palmitoyl-CoA desaturase (N-C16:0CoA -> N-C16:1CoA)
  3. 1-hexadecanoyl-sn-glycero-3-phosphate + (9Z)-hexadecenoyl-CoA = 1-hexadecanoyl-2-[(9Z)-hexadec-9-enoyl]-sn-glycero-3-phosphate + CoA

  Catalysed by DGAT1, LRAT, AWAT1, AWAT2 and 3 morecytosolOne of 2 routes

• 1-hexadecanoyl-2-(9Z)-hexadecenoyl-sn-glycero-3-phosphoethanolamineReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. palmitoyl-CoA desaturase (N-C16:0CoA -> N-C16:1CoA)
  3. 1-hexadecanoyl-sn-glycero-3-phosphoethanolamine + (9Z)-hexadecenoyl-CoA = 1-hexadecanoyl-2-(9Z)-hexadecenoyl-sn-glycero-3-phosphoethanolamine + CoA

  Catalysed by DGAT1, LRAT, AWAT1, AWAT2 and 3 morecytosol

• 1-hexadecanoyl-2-(9Z-hexadecenoyl)-sn-glycero-3-phosphocholineReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. palmitoyl-CoA desaturase (N-C16:0CoA -> N-C16:1CoA)
  3. (9Z)-hexadecenoyl-CoA + 1-hexadecanoyl-sn-glycero-3-phosphocholine = 1-hexadecanoyl-2-(9Z-hexadecenoyl)-sn-glycero-3-phosphocholine + CoA

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

• (9Z,12Z,15Z)-octadecatrienoyl-CoAReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. Palmitoyl-CoA:retinol O-acyltransferase
  3. long-chain-fatty-acid-CoA ligase (linolenate)

  Catalysed by DGAT1, LRAT, AWAT1, AWAT2 and 9 morecytosolOne of 8 routes

• (13Z)-docosenoyl-CoAReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. Palmitoyl-CoA:retinol O-acyltransferase
  3. long-chain-fatty-acid-CoA ligase (cis-erucic acid)

  Catalysed by DGAT1, LRAT, AWAT1, AWAT2 and 9 morecytosolOne of 7 routes

• (11Z)-eicosenoyl-CoAReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. Palmitoyl-CoA:retinol O-acyltransferase
  3. long-chain-fatty-acid-CoA ligase (cis-gondoic acid)

  Catalysed by DGAT1, LRAT, AWAT1, AWAT2 and 9 morecytosolOne of 8 routes

• (9Z,12Z,15Z,18Z,21Z)-tetracosapentaenoyl-CoAReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. Palmitoyl-CoA:retinol O-acyltransferase
  3. long-chain-fatty-acid-CoA ligase ((9Z,12Z,15Z,18Z,21Z)-TPA)

  Catalysed by DGAT1, LRAT, AWAT1, AWAT2 and 9 morecytosolOne of 6 routes

• (6Z,9Z,12Z,15Z,18Z,21Z)-tetracosahexaenoyl-CoAReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. Palmitoyl-CoA:retinol O-acyltransferase
  3. long-chain-fatty-acid-CoA ligase ((6Z,9Z,12Z,15Z,18Z,21Z)-THA)

  Catalysed by DGAT1, LRAT, AWAT1, AWAT2 and 9 morecytosolOne of 5 routes

• 2-hydroxyoctadecanoyl-CoAReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. fatty-acyl-CoA synthase (N-C18:0CoA)
  3. octadecanoyl-CoA + 2-oxoglutarate + O2 = 2-hydroxyoctadecanoyl-CoA + succinate + CO2

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

• (15Z)-tetracosenoyl-CoAReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. Palmitoyl-CoA:retinol O-acyltransferase
  3. long-chain-fatty-acid-CoA ligase (nervonic acid)

  Catalysed by DGAT1, LRAT, AWAT1, AWAT2 and 9 morecytosolOne of 7 routes

• (17Z)-hexacosenoyl-CoAReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. Palmitoyl-CoA:retinol O-acyltransferase
  3. long-chain-fatty-acid-CoA ligase (ximenic acid)

  Catalysed by DGAT1, LRAT, AWAT1, AWAT2 and 9 morecytosolOne of 5 routes

• (8Z,11Z,14Z)-eicosatrienoyl-CoAReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. Palmitoyl-CoA:retinol O-acyltransferase
  3. long-chain-fatty-acid-CoA ligase (dihomo-gamma-linolenate)

  Catalysed by DGAT1, LRAT, AWAT1, AWAT2 and 9 morecytosolOne of 6 routes

• (8Z,11Z,14Z,17Z)-eicosatetraenoyl-CoAReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. Palmitoyl-CoA:retinol O-acyltransferase
  3. long-chain-fatty-acid-CoA ligase (omega-3-arachidonic acid)

  Catalysed by DGAT1, LRAT, AWAT1, AWAT2 and 9 morecytosolOne of 6 routes