11-cis-retinyl hexadecanoate

Three steps

• (S)-carnitineReach 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 256 routes

• CHEBI:1307929Reach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. Acyl-CoA:cholesterol O-acyltransferase
  3. Steryl-ester acylhydrolase

  Catalysed by DGAT1, LRAT, AWAT1, AWAT2 and 5 morecytosol, endoplasmic reticulum, lysosomeOne of 2 routes

• (13S,14S)-epoxy-(4Z,7Z,9E,11E,16Z,19Z)-docosahexaenoateReach from here →
  1. 11-peroxy-docosahexaenoate to DHA conversion
  2. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoate + O2 = (14S)-hydroperoxy-(4Z,7Z,10Z,12E,16Z,19Z)-docosahexaenoate
  3. (14S)-hydroperoxy-(4Z,7Z,10Z,12E,16Z,19Z)-docosahexaenoate = (13S,14S)-epoxy-(4Z,7Z,9E,11E,16Z,19Z)-docosahexaenoate + H2O

  Catalysed by ALOX5, ALOX15, ALOX12cytosol

• S-octanoyl-4'-phosphopantetheineReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. Beta Oxidation of Long Chain Fatty Acid
  3. octanoyl-CoA + H2O = S-octanoyl-4'-phosphopantetheine + adenosine 3',5'-bisphosphate + 2 H(+)

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

• tetradecanoyl-4'-phosphopantetheineReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. Fatty Acid Beta Oxidation (C16->C14), Mitochondrial
  3. tetradecanoyl-CoA + H2O = tetradecanoyl-4'-phosphopantetheine + adenosine 3',5'-bisphosphate + 2 H(+)

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

• an acyl-4'-phosphopantetheineReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. acyl-CoA pool formation and breakdown
  3. an acyl-CoA + H2O = an acyl-4'-phosphopantetheine + adenosine 3',5'-bisphosphate + 2 H(+)

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

• all-trans-3,4-didehydroretinolReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. all-trans-Retinol 11-cis-trans-isomerase
  3. all-trans-retinol + 2 reduced [adrenodoxin] + O2 + 2 H(+) = all-trans-3,4-didehydroretinol + 2 oxidized [adrenodoxin] + 2 H2O

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

• all-trans-4-hydroxyretinolReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. all-trans-Retinol 11-cis-trans-isomerase
  3. all-trans-retinol + 2 reduced [adrenodoxin] + O2 + 2 H(+) = all-trans-4-hydroxyretinol + 2 oxidized [adrenodoxin] + H2O

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

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

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

• N-(9Z-hexadecenoyl)-glycineReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. palmitoyl-CoA desaturase (N-C16:0CoA -> N-C16:1CoA)
  3. (9Z)-hexadecenoyl-CoA + glycine = N-(9Z-hexadecenoyl)-glycine + CoA + H(+)

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

• 2-hydroxyoctanoyl-CoAReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. Beta Oxidation of Long Chain Fatty Acid
  3. octanoyl-CoA + 2-oxoglutarate + O2 = 2-hydroxyoctanoyl-CoA + succinate + CO2

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

• 2-hydroxytetradecanoyl-CoAReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. Fatty Acid Beta Oxidation (C16->C14), Mitochondrial
  3. tetradecanoyl-CoA + 2-oxoglutarate + O2 = 2-hydroxytetradecanoyl-CoA + succinate + CO2

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

• 9-cis-retinyl tetradecanoateReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. 11-cis-retinol = 9-cis-retinol
  3. 9-cis-retinol + tetradecanoyl-CoA = 9-cis-retinyl tetradecanoate + CoA

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

• 13-cis-retinyl tetradecanoateReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. 11-cis-retinol = 13-cis-retinol
  3. 13-cis-retinol + tetradecanoyl-CoA = 13-cis-retinyl tetradecanoate + CoA

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

• all-trans-retinyl tetradecanoateReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. all-trans-Retinol 11-cis-trans-isomerase
  3. all-trans-retinol + tetradecanoyl-CoA = all-trans-retinyl tetradecanoate + CoA

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

• tetradecyl tetradecanoateReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. Fatty Acid Beta Oxidation (C16->C14), Mitochondrial
  3. tetradecan-1-ol + tetradecanoyl-CoA = tetradecyl tetradecanoate + CoA

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

• 13-cis-retinyl hexadecanoateReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. 11-cis-retinol = 13-cis-retinol
  3. 13-cis-retinol + hexadecanoyl-CoA = 13-cis-retinyl hexadecanoate + CoA

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

• 1-(9Z-octadecenoyl)-2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-phosphateReach 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 + 1-(9Z-octadecenoyl)-sn-glycero-3-phosphate = 1-(9Z-octadecenoyl)-2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-phosphate + CoA

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

• 9-cis-retinyl hexadecanoateReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. 11-cis-retinol = 9-cis-retinol
  3. 9-cis-retinol + hexadecanoyl-CoA = 9-cis-retinyl hexadecanoate + CoA

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

• (7S,17S)-dihydroperoxy-(4Z,8E,10Z,13Z,15E,19Z)-docosahexaenoateReach from here →
  1. 11-peroxy-docosahexaenoate to DHA conversion
  2. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoate + O2 = (7S)-hydroperoxy-(4Z,8E,10Z,13Z,16Z,19Z)-docosahexaenoate
  3. (7S)-hydroperoxy-(4Z,8E,10Z,13Z,16Z,19Z)-docosahexaenoate + O2 = (7S,17S)-dihydroperoxy-(4Z,8E,10Z,13Z,15E,19Z)-docosahexaenoate

  Catalysed by ALOX5, ALOX15B, ALOX15, ALOX12cytosol

• N-octanoylglycineReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. Beta Oxidation of Long Chain Fatty Acid
  3. octanoyl-CoA + glycine = N-octanoylglycine + CoA + H(+)

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

• an N-octadecanoyl-sphingoid baseReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. fatty-acyl-CoA synthase (N-C18:0CoA)
  3. a sphingoid base + octadecanoyl-CoA = an N-octadecanoyl-sphingoid base + CoA + H(+)

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

• (7Z)-octadecenoyl-CoAReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. Palmitoyl-CoA:retinol O-acyltransferase
  3. carnitine O-palmitoyltransferase ((7Z)-octadecenoyl-CoA)

  Catalysed by DGAT1, LRAT, AWAT1, AWAT2 and 4 morecytosolOne of 5 routes

• CHEBI:15345Reach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. Palmitoyl-CoA:retinol O-acyltransferase
  3. Acetoacetate:CoA ligase (AMP-forming)

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

• cholineReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. Palmitoyl-CoA:retinol O-acyltransferase
  3. Acetyl-CoA:choline O-acetyltransferase

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

• CHEBI:15380Reach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. Palmitoyl-CoA:retinol O-acyltransferase
  3. 5-aminolevulinate synthase (2-amino-3-oxoadipate)

  Catalysed by DGAT1, LRAT, AWAT1, AWAT2 and 3 morecytosol, mitochondrial matrixOne of 8 routes

• CHEBI:15477Reach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. Palmitoyl-CoA:retinol O-acyltransferase
  3. glycine N-acyltransferase (2-methylbutyryl-CoA)

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

• 2-methylcrotonoyl-CoAReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. Palmitoyl-CoA:retinol O-acyltransferase
  3. Production of Tiglylcarnitine

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

• isobutyryl-CoAReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. Palmitoyl-CoA:retinol O-acyltransferase
  3. acetyl-CoA C-acyltransferase (3-oxo-4-methyl-pentanoyl-CoA)

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

• 3-methylbut-2-enoyl-CoAReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. Palmitoyl-CoA:retinol O-acyltransferase
  3. glycine-N-acyltransferase (3-methylcrotonoylglycine)

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

• isovaleryl-CoAReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. Palmitoyl-CoA:retinol O-acyltransferase
  3. glycine N-acyltransferase (isovalerylglycine)

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

• arachidonoyl-CoAReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. Palmitoyl-CoA:retinol O-acyltransferase
  3. Arachidonate:CoA ligase (AMP-forming)

  Catalysed by DGAT1, LRAT, AWAT1, AWAT2 and 9 morecytosolOne of 12 routes

• CHEBI:15519Reach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. Palmitoyl-CoA:retinol O-acyltransferase
  3. propanoyl-CoA C-acyltransferase

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

• oleoyl-CoAReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. Palmitoyl-CoA:retinol O-acyltransferase
  3. Transport of octadecenoyl-CoA into Mitochondrial Matrix

  Catalysed by DGAT1, LRAT, AWAT1, AWAT2 and 4 morecytosolOne of 15 routes

• phenylacetyl-CoAReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. Palmitoyl-CoA:retinol O-acyltransferase
  3. Phenylacetate:CoA ligase

  Catalysed by DGAT1, LRAT, AWAT1, AWAT2 and 1 morecytosolOne of 3 routes

• propionyl-CoAReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. Palmitoyl-CoA:retinol O-acyltransferase
  3. Propanoate:CoA ligase (AMP-forming)

  Catalysed by DGAT1, LRAT, AWAT1, AWAT2 and 4 morecytosolOne of 43 routes

• (7S,14S)-dihydroperoxy-(4Z,8E,10Z,12E,16Z,19Z)-docosahexaenoateReach from here →
  1. 11-peroxy-docosahexaenoate to DHA conversion
  2. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoate + O2 = (7S)-hydroperoxy-(4Z,8E,10Z,13Z,16Z,19Z)-docosahexaenoate
  3. (7S)-hydroperoxy-(4Z,8E,10Z,13Z,16Z,19Z)-docosahexaenoate + O2 = (7S,14S)-dihydroperoxy-(4Z,8E,10Z,12E,16Z,19Z)-docosahexaenoate

  Catalysed by ALOX5, ALOX15, ALOX12cytosol

• CHEBI:15650Reach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. Palmitoyl-CoA:retinol O-acyltransferase
  3. N-acetyl-LTE4 to leukotriene E4 conversion

  Catalysed by DGAT1, LRAT, AWAT1, AWAT2 and 33 morecytosolOne of 2 routes

• all-trans-3-hydroxyretinolReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. all-trans-Retinol 11-cis-trans-isomerase
  3. all-trans-retinol + 2 reduced [adrenodoxin] + O2 + 2 H(+) = all-trans-3-hydroxyretinol + 2 oxidized [adrenodoxin] + H2O

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

• betaine aldehydeReach 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. choline + A = betaine aldehyde + AH2

  Catalysed by PTGS2, CHDHcytosol

• CHEBI:15727Reach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. Palmitoyl-CoA:retinol O-acyltransferase
  3. N-alpha-acetyltransferase 10, NatA catalytic subunit (acetylcarnosine)

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

• CHEBI:15746Reach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. Palmitoyl-CoA:retinol O-acyltransferase
  3. diamine N-acetyltransferase (N1-acetylspermine)

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

• 1-acylglycerone 3-phosphateReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. acyl-CoA pool formation and breakdown
  3. Acyl-CoA:glycerone-phosphate O-acyltransferase

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

• phosphatidylethanolamineReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. acyl-CoA pool formation and breakdown
  3. Acyl-CoA:1-acyl-sn-glycero-3-phosphoethanolamine O-acyltransferase

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

• 1,2-diacyl-sn-glycero-3-phosphocholine(1+)Reach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. Lecithin Retinol Acyltransferase (11-Cis)
  3. Acyl-CoA:1-acyl-sn-glycero-3-phosphocholine O-acyltransferase

  Catalysed by DGAT1, LRAT, AWAT1, AWAT2 and 5 morecytosolOne of 2 routes

• phosphatidic acidReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. acyl-CoA pool formation and breakdown
  3. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase

  Catalysed by DGAT1, LRAT, AWAT1, AWAT2 and 10 morecytosol, mitochondrial matrixOne of 7 routes

• (R)-carnitineReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. palmitoyl-CoA:L-carnitine O-palmitoyltransferase
  3. (R)-carnitine + hexadecanoyl-CoA = O-hexadecanoyl-(R)-carnitine + CoA

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

• oxaloacetateReach 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. (R)-malate + A = oxaloacetate + AH2

  Catalysed by PTGS2, D2HGDHcytosolOne of 2 routes

• CHEBI:16566Reach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. Palmitoyl-CoA:L-serine C-palmitoyltransferase (decarboxylating)
  3. Sphinganine:NADP+ 3-oxidoreductase

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

• formaldehydeReach 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. N(6),N(6)-dimethyl-L-lysyl(4)-[histone H3] + 2 A + 2 H2O = L-lysyl(4)-[histone H3] + 2 formaldehyde + 2 AH2

  Catalysed by PTGS2, KDM1A, KDM1BcytosolOne of 3 routes