11-cis-retinol

Three steps

• decanoyl-4'-phosphopantetheineReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. medium-chain acyl-CoA ligase (decanoic acid)
  3. decanoyl-CoA + H2O = decanoyl-4'-phosphopantetheine + adenosine 3',5'-bisphosphate + 2 H(+)

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

• S-dodecanoyl-4'-phosphopantetheineReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. long-chain-fatty-acid-CoA ligase (lauric acid)
  3. dodecanoyl-CoA + H2O = S-dodecanoyl-4'-phosphopantetheine + adenosine 3',5'-bisphosphate + 2 H(+)

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

• tetradecanoyl-4'-phosphopantetheineReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. long-chain-fatty-acid-CoA ligase (myristic acid)
  3. tetradecanoyl-CoA + H2O = tetradecanoyl-4'-phosphopantetheine + adenosine 3',5'-bisphosphate + 2 H(+)

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

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

  Catalysed by DGAT1, LRAT, AWAT1, AWAT2 and 8 morecytosol, Golgi apparatus

• 21-hydroxy-(4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoateReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. 11-peroxy-docosahexaenoate to DHA conversion
  3. DHA[r] + O2[r] + FMNH2[r] = FMN[r] + H2O[r] + 21-hydroxy-(4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoate[r]

  Catalysed by DGAT1, LRAT, AWAT1, AWAT2 and 2 morecytosol, endoplasmic reticulumOne of 3 routes

• tauroursodeoxycholateReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. bile acid-CoA:amino acid N-acyltransferase (taurodeoxycholate)
  3. taurine to tauroursodeoxycholate conversion

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

• glycoursodeoxycholateReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. glycine to glycoursodeoxycholate conversion

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

• leukotriene F4Reach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. N-acetyl-LTE4 to leukotriene E4 conversion
  3. leukotriene F4 hydrolysis

  Catalysed by DGAT1, LRAT, AWAT1, AWAT2 and 33 morecytosol

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

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

• 19,20-epoxy-(4Z,7Z,10Z,13Z,16Z)-docosapentaenoateReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. 11-peroxy-docosahexaenoate to DHA conversion
  3. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoate + reduced [NADPH--hemoprotein reductase] + O2 = 19,20-epoxy-(4Z,7Z,10Z,13Z,16Z)-docosapentaenoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

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

• 16,17-epoxy-(4Z,7Z,10Z,13Z,19Z)-docosapentaenoateReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. 11-peroxy-docosahexaenoate to DHA conversion
  3. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoate + reduced [NADPH--hemoprotein reductase] + O2 = 16,17-epoxy-(4Z,7Z,10Z,13Z,19Z)-docosapentaenoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

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

• 13,14-epoxy-(4Z,7Z,10Z,16Z,19Z)-docosapentaenoateReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. 11-peroxy-docosahexaenoate to DHA conversion
  3. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoate + reduced [NADPH--hemoprotein reductase] + O2 = 13,14-epoxy-(4Z,7Z,10Z,16Z,19Z)-docosapentaenoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

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

• 10,11-epoxy-(4Z,7Z,13Z,16Z,19Z)-docosapentaenoateReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. 11-peroxy-docosahexaenoate to DHA conversion
  3. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoate + reduced [NADPH--hemoprotein reductase] + O2 = 10,11-epoxy-(4Z,7Z,13Z,16Z,19Z)-docosapentaenoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

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

• 2,4-dinitrophenyl-S-glutathioneReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. N-acetyl-LTE4 to leukotriene E4 conversion
  3. transport of leukotriene E4 (cytosol to extracellular)

  Catalysed by DGAT1, LRAT, AWAT1, AWAT2 and 34 morecytosol, extracellular spaceOne of 2 routes

• N-(9Z-octadecenoyl)glycineReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. (9Z)-octadecenoyl-CoA + glycine = N-(9Z-octadecenoyl)glycine + CoA + H(+)

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

• N-octadecanoylglycineReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. long-chain-fatty-acid-CoA ligase (stearate)
  3. octadecanoyl-CoA + glycine = N-octadecanoylglycine + CoA + H(+)

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

• N-(9Z-hexadecenoyl)-glycineReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. long-chain-fatty-acid-CoA ligase (palmitolate)
  3. (9Z)-hexadecenoyl-CoA + glycine = N-(9Z-hexadecenoyl)-glycine + CoA + H(+)

  Catalysed by DGAT1, LRAT, AWAT1, AWAT2 and 10 morecytosolOne of 2 routes

• (19R,20S)-epoxy-(4Z,7Z,10Z,13Z,16Z)-docosapentaenoateReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. 11-peroxy-docosahexaenoate to DHA conversion
  3. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoate + reduced [NADPH--hemoprotein reductase] + O2 = (19R,20S)-epoxy-(4Z,7Z,10Z,13Z,16Z)-docosapentaenoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

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

• (19S,20R)-epoxy-(4Z,7Z,10Z,13Z,16Z)-docosapentaenoateReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. 11-peroxy-docosahexaenoate to DHA conversion
  3. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoate + reduced [NADPH--hemoprotein reductase] + O2 = (19S,20R)-epoxy-(4Z,7Z,10Z,13Z,16Z)-docosapentaenoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

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

• a 3-(acyloxy)acyl derivative of bacterial toxinReach from here →
  1. Lecithin Retinol Acyltransferase (11-Cis)
  2. an all-trans-retinyl ester + H2O = 11-cis-retinol + a fatty acid + H(+)
  3. a 3-(acyloxy)acyl derivative of bacterial toxin + H2O = a 3-hydroxyacyl derivative of bacterial toxin + a fatty acid + H(+)

  Catalysed by RPE65, AOAHcytosol

• 2-hydroxyoctanoyl-CoAReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. Octanoyl-CoA:L-carnitine O-octanoyltransferase
  3. octanoyl-CoA + 2-oxoglutarate + O2 = 2-hydroxyoctanoyl-CoA + succinate + CO2

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

• 2-hydroxydecanoyl-CoAReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. medium-chain acyl-CoA ligase (decanoic acid)
  3. decanoyl-CoA + 2-oxoglutarate + O2 = 2-hydroxydecanoyl-CoA + succinate + CO2

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

• 2-hydroxyeicosanoyl-CoAReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. long-chain-fatty-acid-CoA ligase (eicosanoate)
  3. eicosanoyl-CoA + 2-oxoglutarate + O2 = 2-hydroxyeicosanoyl-CoA + succinate + CO2

  Catalysed by DGAT1, LRAT, AWAT1, AWAT2 and 10 morecytosol

• 2-hydroxydodecanoyl-CoAReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. long-chain-fatty-acid-CoA ligase (lauric acid)
  3. dodecanoyl-CoA + 2-oxoglutarate + O2 = 2-hydroxydodecanoyl-CoA + succinate + CO2

  Catalysed by DGAT1, LRAT, AWAT1, AWAT2 and 10 morecytosol

• 2-hydroxytetradecanoyl-CoAReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. long-chain-fatty-acid-CoA ligase (myristic acid)
  3. tetradecanoyl-CoA + 2-oxoglutarate + O2 = 2-hydroxytetradecanoyl-CoA + succinate + CO2

  Catalysed by DGAT1, LRAT, AWAT1, AWAT2 and 10 morecytosol

• tetradecyl tetradecanoateReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. long-chain-fatty-acid-CoA ligase (myristic acid)
  3. tetradecan-1-ol + tetradecanoyl-CoA = tetradecyl tetradecanoate + CoA

  Catalysed by DGAT1, LRAT, AWAT1, AWAT2 and 9 morecytosol

• 1-(9Z-octadecenoyl)-2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-phosphateReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  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 DGAT1, LRAT, AWAT1, AWAT2 and 10 morecytosol

• all-trans-4-hydroxyretinalReach from here →
  1. all-trans-Retinol 11-cis-trans-isomerase
  2. all-trans-retinol + 2 reduced [adrenodoxin] + O2 + 2 H(+) = all-trans-4-hydroxyretinol + 2 oxidized [adrenodoxin] + H2O
  3. NAD+[c] + all-trans-4-hydroxyretinol[c] = H+[c] + NADH[c] + all-trans-4-hydroxyretinal[c]

  Catalysed by CYP27C1, ADH1BcytosolOne of 2 routes

• N-hexadecanoylglycineReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. hexadecanoyl-CoA + glycine = N-hexadecanoylglycine + CoA + H(+)

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

• N-dodecanoylglycineReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. long-chain-fatty-acid-CoA ligase (lauric acid)
  3. dodecanoyl-CoA + glycine = N-dodecanoylglycine + CoA + H(+)

  Catalysed by DGAT1, LRAT, AWAT1, AWAT2 and 10 morecytosolOne of 2 routes

• N-decanoylglycineReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. medium-chain acyl-CoA ligase (decanoic acid)
  3. decanoyl-CoA + glycine = N-decanoylglycine + CoA + H(+)

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

• N-octanoylglycineReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. Octanoyl-CoA:L-carnitine O-octanoyltransferase
  3. octanoyl-CoA + glycine = N-octanoylglycine + CoA + H(+)

  Catalysed by DGAT1, LRAT, AWAT1, AWAT2 and 3 morecytosol, mitochondrial matrixOne of 2 routes

• N(1)-(5-phospho-beta-D-ribosyl)glycinamideReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. 5-phospho-beta-D-ribosylamine + glycine + ATP = N(1)-(5-phospho-beta-D-ribosyl)glycinamide + ADP + phosphate + H(+)

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

• L-cystine-bis-glycineReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. L-cystine-bis-glycine + 2 H2O = L-cystine + 2 glycine

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

• an N-octadecanoyl-sphingoid baseReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. long-chain-fatty-acid-CoA ligase (stearate)
  3. a sphingoid base + octadecanoyl-CoA = an N-octadecanoyl-sphingoid base + CoA + H(+)

  Catalysed by DGAT1, LRAT, AWAT1, AWAT2 and 9 morecytosol

• glycyldehydrophenylalanineReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. glycyldehydrophenylalanine + H2O = 2,3-didehydrophenylalanine + glycine

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

• 1,2,3-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-glycerolReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. 11-peroxy-docosahexaenoate to DHA conversion
  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 DGAT1, LRAT, AWAT1, AWAT2 and 2 morecytosol

• an N-(fatty acyl)-glycineReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. a fatty acyl-CoA + glycine = an N-(fatty acyl)-glycine + CoA + H(+)

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

• 1-(10Z-heptadecenoyl)-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphoethanolamineReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. long-chain-fatty-acid-CoA ligase ((6Z,9Z)-octadecadienoic acid)
  3. 1-(10Z-heptadecenoyl)-sn-glycero-3-phosphoethanolamine + (9Z,12Z)-octadecadienoyl-CoA = 1-(10Z-heptadecenoyl)-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphoethanolamine + CoA

  Catalysed by DGAT1, LRAT, AWAT1, AWAT2 and 10 morecytosol

• N-(9Z,12Z-octadecadienoyl)-glycineReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. long-chain-fatty-acid-CoA ligase ((6Z,9Z)-octadecadienoic acid)
  3. (9Z,12Z)-octadecadienoyl-CoA + glycine = N-(9Z,12Z-octadecadienoyl)-glycine + CoA + H(+)

  Catalysed by DGAT1, LRAT, AWAT1, AWAT2 and 10 morecytosolOne of 2 routes

• cholesteryl (7Z)-octadecenoateReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. carnitine O-palmitoyltransferase ((7Z)-octadecenoyl-CoA)
  3. (7Z)-octadecenoyl-CoA + cholesterol = cholesteryl (7Z)-octadecenoate + CoA

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

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

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

• pyruvateReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. (R)-3-Amino-2-methylpropanoate:pyruvate aminotransferase

  Catalysed by DGAT1, LRAT, AWAT1, AWAT2 and 2 morecytosol, mitochondrial matrixOne of 20 routes

• all-trans-retinoic acidReach from here →
  1. all-trans-Retinol 11-cis-trans-isomerase
  2. retinol: NADP+ oxidoreductase
  3. retinal:NAD+ oxidoreductase

  Catalysed by DHRS3, RDH10, RDH11, RDH12 and 5 morecytosolOne of 4 routes

• CHEBI:15467Reach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. Acetoacetate:CoA ligase (AMP-forming)
  3. 3-hydroxy-3-methylglutaryl-CoA synthase (acetoacetyl-CoA)

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

• CHEBI:15570Reach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. transport of D-alanine and glycine (cytosol to extracellular)

  Catalysed by DGAT1, LRAT, AWAT1, AWAT2 and 6 morecytosol, mitochondrial matrix, extracellular spaceOne of 3 routes

• (S)-malateReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. ATP citrate lyase (citrate)
  3. transport of malate and OAA (cytosol to mitochondria)

  Catalysed by DGAT1, LRAT, AWAT1, AWAT2 and 2 morecytosol, mitochondrial matrixOne of 5 routes

• L-leucineReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. transport of glycine and leucine (cytosol to extracellular)

  Catalysed by DGAT1, LRAT, AWAT1, AWAT2 and 5 morecytosol, mitochondrial matrix, extracellular spaceOne of 21 routes

• (7S)-hydroperoxy-(4Z,8E,10Z,13Z,16Z,19Z)-docosahexaenoateReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. 11-peroxy-docosahexaenoate to DHA conversion
  3. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoate + O2 = (7S)-hydroperoxy-(4Z,8E,10Z,13Z,16Z,19Z)-docosahexaenoate

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

• CHEBI:15611Reach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. S-Adenosyl-L-methionine:glycine N-methyltransferase

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