11-cis-retinol

Three steps

• glycerolReach from here →
  1. Lecithin Retinol Acyltransferase (11-Cis)
  2. 1-Acyl-sn-glycero-3-phosphocholine acylhydrolase
  3. sn-glycerol 3-phosphocholine + H2O = phosphocholine + glycerol + H(+)

  Catalysed by LYPLA1, LYPLA2, PLA2G4A, PLB1 and 7 morecytosol

• CHEBI:17769Reach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. diamine N-acetyltransferase (N1-acetylspermidine)
  3. spermidine:(acceptor) oxidoreductase

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

• a 1,2-diacyl-sn-glycerolReach from here →
  1. Lecithin Retinol Acyltransferase (11-Cis)
  2. Acyl-CoA:1-acyl-sn-glycero-3-phosphocholine O-acyltransferase
  3. ceramide:phosphatidylcholine cholinephosphotransferase

  Catalysed by LPCAT4, LPCAT3, LPCAT2, LPCAT1 and 2 morecytosol, Golgi apparatusOne of 5 routes

• a triacylglycerolReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. acyl-CoA:sphingosine N-acyltransferase
  3. acyl-CoA:1,2-diacyl-sn-glycerol O-acyltransferase

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

• CHEBI:17895Reach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. transport of glycine and tyrosine (cytosol to extracellular)

  Catalysed by DGAT1, LRAT, AWAT1, AWAT2 and 5 morecytosol, mitochondrial matrix, extracellular spaceOne of 19 routes

• butanoateReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. Butanoate:CoA ligase (AMP-forming)
  3. butanoyl-CoA + H2O = butanoate + CoA + H(+)

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

• CHEBI:18019Reach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. transport of glycine and lysine (cytosol to extracellular)

  Catalysed by DGAT1, LRAT, AWAT1, AWAT2 and 5 morecytosol, mitochondrial matrix, extracellular spaceOne of 10 routes

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

  Catalysed by DGAT1, LRAT, AWAT1, AWAT2 and 5 morecytosol, mitochondrial matrix, extracellular spaceOne of 29 routes

• spermine monoaldehydeReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. diamine N-acetyltransferase (N1-acetylspermine)
  3. primary-amine oxidase (spermine)

  Catalysed by DGAT1, LRAT, AWAT1, AWAT2 and 6 morecytosolOne of 3 routes

• CHEBI:18095Reach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. Transport of Hydroxy-Proline

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

• O-octanoyl-(R)-carnitineReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. Carnitine O-Palmitoyltransferase
  3. solute carrier (L-carnitine)

  Catalysed by DGAT1, LRAT, AWAT1, AWAT2 and 5 morecytosol, mitochondrial matrixOne of 11 routes

• CHEBI:18132Reach from here →
  1. Lecithin Retinol Acyltransferase (11-Cis)
  2. 1-Acyl-sn-glycero-3-phosphocholine acylhydrolase
  3. sn-Glycero-3-phosphocholine cholinephosphohydrolase

  Catalysed by LYPLA1, LYPLA2, PLA2G4A, PLB1 and 7 morecytosolOne of 2 routes

• dodecanoateReach from here →
  1. Lecithin Retinol Acyltransferase (11-Cis)
  2. 1-Acyl-sn-glycero-3-phosphocholine acylhydrolase
  3. (10Z)-heptadecenoic acid formation

  Catalysed by LYPLA1, LYPLA2, PLA2G4A, PLB1 and 6 morecytosol, extracellular spaceOne of 14 routes

• phosphatidyl-L-serineReach from here →
  1. Lecithin Retinol Acyltransferase (11-Cis)
  2. Acyl-CoA:1-acyl-sn-glycero-3-phosphocholine O-acyltransferase
  3. phosphatidylserine synthase (PC-LD pool)

  Catalysed by LPCAT4, LPCAT3, LPCAT2, LPCAT1 and 1 morecytosol

• N(1)-(5-phospho-D-ribosyl)glycinamideReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. 5-Phospho-D-ribosylamine:glycine ligase (ADP-forming)

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

• N-(4-aminobutyl)-3-aminopropanalReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. diamine N-acetyltransferase (N1-acetylspermidine)
  3. primary-amine oxidase (spermidine)

  Catalysed by DGAT1, LRAT, AWAT1, AWAT2 and 6 morecytosolOne of 3 routes

• (2E,5Z,8Z,11Z,14Z,17Z)-eicosahexaenoyl-CoAReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. long-chain-fatty-acid-CoA ligase (EPA)
  3. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA + O2 = (2E,5Z,8Z,11Z,14Z,17Z)-eicosahexaenoyl-CoA + H2O2

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

• 1-octadecanoyl-2-acyl-sn-glycero-3-phosphoethanolamineReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. long-chain-fatty-acid-CoA ligase (stearate)
  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 9 morecytosol

• ophthalmateReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. gamma-L-glutamyl-(2S)-2-aminobutanoate + glycine + ATP = ophthalmate + ADP + phosphate + H(+)

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

• S-methylmercury-L-cysteineReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. N-acetylglutamate synthase (N-acetylmethionine)
  3. S-methylmercury-L-cysteine(out) + L-methionine(in) = S-methylmercury-L-cysteine(in) + L-methionine(out)

  Catalysed by DGAT1, LRAT, AWAT1, AWAT2 and 3 morecytosol, mitochondrial matrix, inner side of the membrane, outer side of the membraneOne of 2 routes

• 2-aminoisobutanoateReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. 2-aminoisobutanoate(out) + L-alanine(in) = 2-aminoisobutanoate(in) + L-alanine(out)

  Catalysed by DGAT1, LRAT, AWAT1, AWAT2 and 2 morecytosol, mitochondrial matrix, inner side of the membrane, outer side of the membraneOne of 2 routes

• 5-(3,3-dimethylguanidino)-2-oxopentanoateReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. ATP citrate lyase (citrate)
  3. N(omega),N(omega)-dimethyl-L-arginine + oxaloacetate = 5-(3,3-dimethylguanidino)-2-oxopentanoate + L-aspartate

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

• N(omega),N('omega)-dimethyl-L-arginineReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. N(omega),N('omega)-dimethyl-L-arginine + glyoxylate = 5-(3,3'-dimethylguanidino)-2-oxopentanoate + glycine

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

• 1-butanoyl-2-(9Z-octadecenoyl)-glycerolReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. Butanoate:CoA ligase (AMP-forming)
  3. 2-(9Z-octadecenoyl)-glycerol + butanoyl-CoA = 1-butanoyl-2-(9Z-octadecenoyl)-glycerol + CoA

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

• 1-octanoyl-2-(9Z-octadecenoyl)-glycerolReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. Octanoyl-CoA:L-carnitine O-octanoyltransferase
  3. 2-(9Z-octadecenoyl)-glycerol + octanoyl-CoA = 1-octanoyl-2-(9Z-octadecenoyl)-glycerol + CoA

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

• 1-eicosanoyl-2-(9Z-octadecenoyl)-glycerolReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. long-chain-fatty-acid-CoA ligase (eicosanoate)
  3. eicosanoyl-CoA + 2-(9Z-octadecenoyl)-glycerol = 1-eicosanoyl-2-(9Z-octadecenoyl)-glycerol + CoA

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

• 5,6,7,8-tetrahydrofolic acidReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. 5,10-Methylenetetrahydrofolate:glycine hydroxymethyltransferase

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

• O-butanoyl-(R)-carnitineReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. Butanoate:CoA ligase (AMP-forming)
  3. butanoyl-CoA + (R)-carnitine = O-butanoyl-(R)-carnitine + CoA

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

• S-disulfanyl-L-cysteineReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. N-acetylglutamate synthase (N-acetyl-L-cysteine)
  3. S-sulfanyl-L-cysteine + L-cysteine = S-disulfanyl-L-cysteine + L-alanine

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

• 3-oxo-(9Z)-eicosenoyl-CoAReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. carnitine O-palmitoyltransferase ((7Z)-octadecenoyl-CoA)
  3. very-long-chain 3-oxoacyl-CoA synthase ((7Z)-octadecenoyl-CoA)

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

• S-hexadecanoyl-N-acetylcysteamineReach from here →
  1. all-trans-retinyl hexadecanoate + H2O = 11-cis-retinol + hexadecanoate + H(+)
  2. all-trans-retinyl hexadecanoate + H2O = all-trans-retinol + hexadecanoate + H(+)
  3. S-hexadecanoyl-N-acetylcysteamine + H2O = N-acetylcysteamine + hexadecanoate + H(+)

  Catalysed by RPE65, PNLIP, PNPLA4, LIPE and 2 more

• S-hexadecanoyl-N-acetylcysteine methyl esterReach from here →
  1. all-trans-retinyl hexadecanoate + H2O = 11-cis-retinol + hexadecanoate + H(+)
  2. all-trans-retinyl hexadecanoate + H2O = all-trans-retinol + hexadecanoate + H(+)
  3. S-hexadecanoyl-N-acetylcysteine methyl ester + H2O = N-acetylcysteine methyl ester + hexadecanoate + H(+)

  Catalysed by RPE65, PNLIP, PNPLA4, LIPE and 1 more

• (2E,6Z,9Z,12Z)-octadecatetraenoyl-CoAReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. long-chain-fatty-acid-CoA ligase (gamma-linolenate)
  3. (6Z,9Z,12Z)-octadecatrienoyl-CoA + oxidized [electron-transfer flavoprotein] + H(+) = (2E,6Z,9Z,12Z)-octadecatetraenoyl-CoA + reduced [electron-transfer flavoprotein]

  Catalysed by DGAT1, LRAT, AWAT1, AWAT2 and 12 morecytosolOne of 2 routes

• (2E,7Z,10Z)-hexadecatrienoyl-CoAReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. Fatty Acid Beta Oxidation Trans (C18:2->C16:2), Mitochondrial
  3. (7Z,10Z)-hexadecadienoyl-CoA + oxidized [electron-transfer flavoprotein] + H(+) = (2E,7Z,10Z)-hexadecatrienoyl-CoA + reduced [electron-transfer flavoprotein]

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

• (2E,4Z,7Z,10Z,13Z)-hexadecapentaenoyl-CoAReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. Fatty Acid Beta Oxidation (C18:4->C16:4), Mitochondrial
  3. Fatty Acid Beta Oxidation (C16:4->C16:5), Mitochondrial

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

• (2E,7Z,10Z,13Z)-hexadecatetraenoyl-CoAReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. Fatty Acid Beta Oxidation (C18:3->C16:3), Mitochondrial
  3. (7Z,10Z,13Z)-hexadecatrienoyl-CoA + oxidized [electron-transfer flavoprotein] + H(+) = (2E,7Z,10Z,13Z)-hexadecatetraenoyl-CoA + reduced [electron-transfer flavoprotein]

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

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

  Catalysed by DGAT1, LRAT, AWAT1, AWAT2 and 5 morecytosol, mitochondrial matrixOne of 3 routes

• NAADPHReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. 11-peroxy-docosahexaenoate to DHA conversion
  3. NAADPH + 2 O2 = NAADP(+) + 2 superoxide + H(+)

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

• docosanoateReach from here →
  1. Lecithin Retinol Acyltransferase (11-Cis)
  2. 1-Acyl-sn-glycero-3-phosphocholine acylhydrolase
  3. (10Z)-heptadecenoic acid formation

  Catalysed by LYPLA1, LYPLA2, PLA2G4A, PLB1 and 6 morecytosol, extracellular spaceOne of 16 routes

• CHEBI:240943Reach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. glycine N-acyltransferase (2-methylbutyryl-CoA)

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

• octadecanoateReach from here →
  1. Lecithin Retinol Acyltransferase (11-Cis)
  2. 1-Acyl-sn-glycero-3-phosphocholine acylhydrolase
  3. (10Z)-heptadecenoic acid formation

  Catalysed by LYPLA1, LYPLA2, PLA2G4A, PLB1 and 6 morecytosol, extracellular spaceOne of 16 routes

• octanoateReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. Octanoyl-CoA:L-carnitine O-octanoyltransferase
  3. Octanoyl-CoA hydrolase

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

• alpha-linolenic acidReach from here →
  1. Lecithin Retinol Acyltransferase (11-Cis)
  2. 1-Acyl-sn-glycero-3-phosphocholine acylhydrolase
  3. (10Z)-heptadecenoic acid formation

  Catalysed by LYPLA1, LYPLA2, PLA2G4A, PLB1 and 6 morecytosol, extracellular spaceOne of 14 routes

• phenylacetylglycineReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. phenylacetyl-CoA:glycine N-phenylacetyltransferase

  Catalysed by DGAT1, LRAT, AWAT1, AWAT2 and 4 morecytosol, mitochondrial matrixOne of 6 routes

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

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

• hexacosan-1-olReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. long-chain-fatty-acid-CoA ligase (cerotic acid)
  3. hexacosanoyl-CoA + 2 NADPH + 2 H(+) = hexacosan-1-ol + 2 NADP(+) + CoA

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

• CHEBI:28666Reach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. N-acetyl-LTE4 to leukotriene E4 conversion
  3. LTD4 hydrolysis

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

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

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

• pyridoxine 5'-phosphateReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. L-selenocysteine selenide-lyase (L-alanine-forming)

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

• N-acetyl-L-cysteineReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. N-acetylglutamate synthase (N-acetyl-L-cysteine)
  3. N-acetylglutamate synthase (N-acetyl-L-cysteine)

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