11-cis-retinyl hexadecanoate

Three steps

• sn-glycerol 3-phosphocholineReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. Lecithin Retinol Acyltransferase (11-Cis)
  3. 1-Acyl-sn-glycero-3-phosphocholine acylhydrolase

  Catalysed by DGAT1, LRAT, AWAT1, AWAT2 and 11 morecytosol

• 1-acyl-sn-glycerol 3-phosphateReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. glycerol-3-phosphate 1-O-acyltransferase (palmitoyl-CoA)
  3. 1-acylglycerol-3P-LD-TG1 pool (liver tissue) formation

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

• a cholesterol esterReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. Acyl-CoA:cholesterol O-acyltransferase
  3. cholesterol-ester plasma pool to cholesterol-ester-10,13,16,19-docosa conversion

  Catalysed by DGAT1, LRAT, AWAT1, AWAT2 and 3 morecytosol, endoplasmic reticulumOne of 4 routes

• CHEBI:17208Reach from here →
  1. 11-peroxy-docosahexaenoate to DHA conversion
  2. ascorbate to dehydroascorbic acid conversion
  3. 7-hydroperoxy-H4-neuroprostane to 7-hydroxy-E4-neuroprostane conversion

  No catalyst recordedcytosolOne of 15 routes

• S-(9Z-hexadecenoyl)-4'-phosphopantetheineReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. palmitoyl-CoA desaturase (N-C16:0CoA -> N-C16:1CoA)
  3. (9Z)-hexadecenoyl-CoA + H2O = S-(9Z-hexadecenoyl)-4'-phosphopantetheine + adenosine 3',5'-bisphosphate + 2 H(+)

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

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

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

• anilineReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. Palmitoyl-CoA:retinol O-acyltransferase
  3. Acetyl-CoA:arylamine N-acetyltransferase

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

• CHEBI:17312Reach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. Palmitoyl-CoA:retinol O-acyltransferase
  3. N1,N12-diacetylspermine to N1-acetylspermine conversion

  Catalysed by DGAT1, LRAT, AWAT1, AWAT2 and 1 morecytosolOne of 2 routes

• linoleic acidReach 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-(alk-1-enyl)-2-acyl-sn-glycero-3-phosphoethanolamineReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. acyl-CoA pool formation and breakdown
  3. Acyl-CoA:1-alkenylglycerophosphoethanolamine O-acyltransferase

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

• AH2Reach 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. A + NADH + H(+) = AH2 + NAD(+)

  Catalysed by PTGS2, AIFM1, PYROXD1cytosolOne of 19 routes

• L-cysteineReach 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, MOCOScytosolOne of 2 routes

• hexadecanalReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. Palmitoyl-CoA hydrolase
  3. 2 H+[c] + NADH[c] + palmitate[c] = H2O[c] + hexadecanal[c] + NAD+[c]

  Catalysed by DGAT1, LRAT, AWAT1, AWAT2 and 9 morecytosolOne of 2 routes

• (7Z,10Z,13Z)-hexadecatrienoyl-CoAReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. Palmitoyl-CoA:retinol O-acyltransferase
  3. Fatty Acid Beta Oxidation (C18:3->C16:3), Mitochondrial

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

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

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

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

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

• all-trans-retinalReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. all-trans-Retinol 11-cis-trans-isomerase
  3. retinol: NADP+ oxidoreductase

  Catalysed by DGAT1, LRAT, AWAT1, AWAT2 and 7 morecytosolOne of 6 routes

• CHEBI:17927Reach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. Palmitoyl-CoA:retinol O-acyltransferase
  3. N1,N8-diacetylspermidine to N1-acetylspermidine conversion

  Catalysed by DGAT1, LRAT, AWAT1, AWAT2 and 1 morecytosol

• a diacylglycerolReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. all-trans-Retinol 11-cis-trans-isomerase
  3. a triacylglycerol + all-trans-retinol = an all-trans-retinyl ester + a diacylglycerol

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

• O-octanoyl-(R)-carnitineReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. Beta Oxidation of Long Chain Fatty Acid
  3. Octanoyl-CoA:L-carnitine O-octanoyltransferase

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

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

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

• 13-cis-retinyl esterReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. 11-cis-retinol = 13-cis-retinol
  3. 13-cis-retinol + a fatty acyl-CoA = 13-cis-retinyl ester + CoA

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

• 9-cis-retinyl esterReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. 11-cis-retinol = 9-cis-retinol
  3. 9-cis-retinol + a fatty acyl-CoA = 9-cis-retinyl ester + CoA

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

• (17S)-hydroxy-(4Z,7Z,10Z,13Z,15E,19Z)-docosahexaenoateReach from here →
  1. 11-peroxy-docosahexaenoate to DHA conversion
  2. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoate + O2 = (17S)-hydroperoxy-(4Z,7Z,10Z,13Z,15E,19Z)-docosahexaenoate
  3. (17S)-hydroperoxy-(4Z,7Z,10Z,13Z,15E,19Z)-docosahexaenoate + 2 glutathione = (17S)-hydroxy-(4Z,7Z,10Z,13Z,15E,19Z)-docosahexaenoate + glutathione disulfide + H2O

  Catalysed by ALOX5, ALOX15, GPX1, GPX4cytosol

• 1-octanoyl-2-(9Z-octadecenoyl)-glycerolReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. Beta Oxidation of Long Chain Fatty Acid
  3. 2-(9Z-octadecenoyl)-glycerol + octanoyl-CoA = 1-octanoyl-2-(9Z-octadecenoyl)-glycerol + CoA

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

• 1,2-di-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-glycerolReach from here →
  1. 11-peroxy-docosahexaenoate to DHA conversion
  2. 1,2,3-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-glycerol + H2O = 1,2-di-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-glycerol + (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoate + H(+)
  3. 1,2,3-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-glycerol + H2O = 1,2-di-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-glycerol + (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoate + H(+)

  Catalysed by DAGLBcytosol

• (5Z)-dodecenoyl-CoAReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. Palmitoyl-CoA:retinol O-acyltransferase
  3. acetyl-CoA C-acyltransferase (3-oxomyrist-7-enoyl-CoA)

  Catalysed by DGAT1, LRAT, AWAT1, AWAT2 and 4 morecytosol, mitochondrial matrixOne of 2 routes

• (11Z)-docosenoyl-CoA(4-)Reach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. Palmitoyl-CoA:retinol O-acyltransferase
  3. long-chain-fatty-acid-CoA ligase (cis-cetoleic acid)

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

• (7Z)-tetradecenoyl-CoAReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. Palmitoyl-CoA:retinol O-acyltransferase
  3. long-chain-fatty-acid-CoA ligase ((7Z)-tetradecenoic acid)

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

• (4Z,7Z,10Z,13Z)-hexadecatetraenoyl-CoAReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. Palmitoyl-CoA:retinol O-acyltransferase
  3. Fatty Acid Beta Oxidation (C18:4->C16:4), Mitochondrial

  Catalysed by DGAT1, LRAT, AWAT1, AWAT2 and 4 morecytosol, mitochondrial matrixOne of 3 routes

• (7Z,10Z)-hexadecadienoyl-CoAReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. Palmitoyl-CoA:retinol O-acyltransferase
  3. Fatty Acid Beta Oxidation Trans (C18:2->C16:2), Mitochondrial

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

• (4Z,7Z)-decadienoyl-CoAReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. Palmitoyl-CoA:retinol O-acyltransferase
  3. Fatty Acid Beta Oxidation (C12:3->C10:2), Mitochondrial

  Catalysed by DGAT1, LRAT, AWAT1, AWAT2 and 4 morecytosol, mitochondrial matrixOne of 2 routes

• (5Z)-octenoyl-CoAReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. Palmitoyl-CoA:retinol O-acyltransferase
  3. Fatty Acid Beta Oxidation (C10:2->C8:1), Mitochondrial

  Catalysed by DGAT1, LRAT, AWAT1, AWAT2 and 4 morecytosol, mitochondrial matrixOne of 2 routes

• docosanoateReach 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

• octadecanoateReach 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 17 routes

• octanoateReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. Beta Oxidation of Long Chain Fatty Acid
  3. Octanoyl-CoA hydrolase

  Catalysed by DGAT1, LRAT, AWAT1, AWAT2 and 4 morecytosol, mitochondrial matrixOne of 2 routes

• alpha-linolenic acidReach 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

• CHEBI:27540Reach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. Palmitoyl-CoA:retinol O-acyltransferase
  3. medium-chain acyl-CoA ligase (hexanoic acid)

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

• elaidic acidReach 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 19 routes

• CHEBI:28701Reach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. Palmitoyl-CoA:retinol O-acyltransferase
  3. Propanoyl-CoA:acetyl-CoA C-acyltransferase

  Catalysed by DGAT1, LRAT, AWAT1, AWAT2 and 4 morecytosol, peroxisomeOne of 7 routes

• a fatty acidReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. Lecithin Retinol Acyltransferase (11-Cis)
  3. an all-trans-retinyl ester + H2O = 11-cis-retinol + a fatty acid + H(+)

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

• tetradecanoateReach 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 14 routes

• (9Z)-octadecenoateReach 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

• hexacosanoateReach 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

• tetracosanoateReach 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

• an N-acylsphinganineReach from here →
  1. 11-peroxy-docosahexaenoate to DHA conversion
  2. (10Z)-heptadecenoic acid formation
  3. N-acylsphingosine amidohydrolase

  Catalysed by ASAH1, ACER2, ACER1, ASAH2 and 1 morecytosolOne of 2 routes

• octadecan-1-olReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. fatty-acyl-CoA synthase (N-C18:0CoA)
  3. octadecanoyl-CoA + 2 NADPH + 2 H(+) = octadecan-1-ol + 2 NADP(+) + CoA

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

• eicosanoateReach 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

• (9Z)-hexadecenoateReach 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 14 routes