11-cis-retinol

Three steps

• (11S)-hydroperoxy-(4Z,7Z,9E,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 = (11S)-hydroperoxy-(4Z,7Z,9E,13Z,16Z,19Z)-docosahexaenoate

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

• CHEBI:15699Reach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. transport of glycine and homoserine (cytosol to extracellular)

  Catalysed by DGAT1, LRAT, AWAT1, AWAT2 and 5 morecytosol, mitochondrial matrix, extracellular spaceOne of 17 routes

• betaine aldehydeReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. Acetyl-CoA:choline O-acetyltransferase
  3. choline dehydrogenase (choline)

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

• trimethylenediamineReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. diamine N-acetyltransferase (N1-acetylspermidine)
  3. deoxyhypusine synthase (1,3-diaminopropane)

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

• hexadecanoic 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 16 routes

• 1-acylglycerone 3-phosphateReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. acyl-CoA:sphingosine N-acyltransferase
  3. Acyl-CoA:glycerone-phosphate O-acyltransferase

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

• CHEBI:15971Reach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. transport of glycine and histidine (cytosol to extracellular)

  Catalysed by DGAT1, LRAT, AWAT1, AWAT2 and 5 morecytosol, mitochondrial matrix, extracellular spaceOne of 11 routes

• CHEBI:15978Reach from here →
  1. Lecithin Retinol Acyltransferase (11-Cis)
  2. 1-Acyl-sn-glycero-3-phosphocholine acylhydrolase
  3. sn-Glycero-3-phosphocholine glycerophosphohydrolase

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

• phosphatidylethanolamineReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. acyl-CoA:sphingosine N-acyltransferase
  3. Acyl-CoA:1-acyl-sn-glycero-3-phosphoethanolamine O-acyltransferase

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

• hexadecan-1-olReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. Palmitoyl-CoA:retinol O-acyltransferase
  3. formate dehydrogenase (palmitoyl-CoA)

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

• L-cystineReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. Transport of L-Cystine (L-Alanine antiport) by B0, +At Transporter

  Catalysed by DGAT1, LRAT, AWAT1, AWAT2 and 3 morecytosol, mitochondrial matrix, extracellular spaceOne of 5 routes

• (R)-3-aminoisobutyric acidReach 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 matrix

• phosphatidic acidReach from here →
  1. Lecithin Retinol Acyltransferase (11-Cis)
  2. Acyl-CoA:1-acyl-sn-glycero-3-phosphocholine O-acyltransferase
  3. phosphatidylcholine phosphatidohydrolase

  Catalysed by LPCAT4, LPCAT3, LPCAT2, LPCAT1 and 3 morecytosolOne of 11 routes

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

  Catalysed by DGAT1, LRAT, AWAT1, AWAT2 and 7 morecytosol, mitochondrial matrix, extracellular spaceOne of 8 routes

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

  Catalysed by DGAT1, LRAT, AWAT1, AWAT2 and 5 morecytosol, mitochondrial matrix, extracellular spaceOne of 20 routes

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

  Catalysed by DGAT1, LRAT, AWAT1, AWAT2 and 5 morecytosol, mitochondrial matrix, extracellular spaceOne of 18 routes

• CHEBI:16523Reach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. transport of D-serine and glycine (cytosol to extracellular)

  Catalysed by DGAT1, LRAT, AWAT1, AWAT2 and 6 morecytosol, mitochondrial matrix, extracellular spaceOne of 2 routes

• protein polypeptide chainReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. PROTEIN_BS

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

• CHEBI:16633Reach 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

• Met-tRNA(Met)Reach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. N-acetylglutamate synthase (N-acetylmethionine)
  3. L-Methionine:tRNAMet ligase (AMP-forming)

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

• 4-methylsulfanyl-2-oxobutanoateReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. N-acetylglutamate synthase (N-acetylmethionine)
  3. glyoxylate + L-methionine = 4-methylsulfanyl-2-oxobutanoate + glycine

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

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

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

• formaldehydeReach from here →
  1. all-trans-Retinol 11-cis-trans-isomerase
  2. all-trans-13,14-dihydroretinol + A = all-trans-retinol + AH2
  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 RETSAT, KDM1A, KDM1BcytosolOne of 3 routes

• CHEBI:16856Reach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. N-acetyl-LTE4 to leukotriene E4 conversion
  3. transport of GSH and leukotriene E4 (cytosol to extracellular)

  Catalysed by DGAT1, LRAT, AWAT1, AWAT2 and 34 morecytosol, extracellular spaceOne of 4 routes

• CHEBI:16857Reach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. transport of glycine and threonine (cytosol to extracellular)

  Catalysed by DGAT1, LRAT, AWAT1, AWAT2 and 7 morecytosol, mitochondrial matrix, extracellular spaceOne of 19 routes

• pantetheine 4'-phosphateReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. acid phosphatase 2, lysosomal (CoA)
  3. Dephospho-CoA nucleotidohydrolase

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

• psychosineReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. acyl-CoA:sphingosine N-acyltransferase
  3. UDP-alpha-D-galactose:sphingosine 1-beta-galactosyltransferase

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

• glyoxylic acidReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. glycine:oxygen oxidoreductase (deaminating)

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

• 1-acyl-sn-glycerol 3-phosphateReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. acyl-CoA:sphingosine N-acyltransferase
  3. acyl-CoA:sn-glycerol-3-phosphate 1-O-acyltransferase

  Catalysed by DGAT1, LRAT, AWAT1, AWAT2 and 9 morecytosol, Golgi apparatus, mitochondrial matrix

• a cholesterol esterReach from here →
  1. Lecithin Retinol Acyltransferase (11-Cis)
  2. Acyl-CoA:1-acyl-sn-glycero-3-phosphocholine O-acyltransferase
  3. Phosphatidylcholine:sterol O-acyltransferase

  Catalysed by LPCAT4, LPCAT3, LPCAT2, LPCAT1 and 1 morecytosolOne of 3 routes

• taurolithocholateReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. bile acid-CoA:amino acid N-acyltransferase (taurodeoxycholate)
  3. bile acid-CoA:amino acid N-acyltransferase (lithocholate)

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

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

  Catalysed by DGAT1, LRAT, AWAT1, AWAT2 and 5 morecytosol, mitochondrial matrix, extracellular spaceOne of 18 routes

• CHEBI:17203Reach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. transport of glycine and proline (cytosol to extracellular)

  Catalysed by DGAT1, LRAT, AWAT1, AWAT2 and 6 morecytosol, mitochondrial matrix, extracellular spaceOne of 15 routes

• S-(4,8-dimethylnonanoyl)-4'-phosphopantetheineReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. Carnitine Dimethyl Nonanoyl Transferase, Revsible, Peroxisomal
  3. 4,8-dimethylnonanoyl-CoA + H2O = S-(4,8-dimethylnonanoyl)-4'-phosphopantetheine + adenosine 3',5'-bisphosphate + 2 H(+)

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

• S-(9Z,12Z,15Z-octadecatrienoyl)-4'-phosphopantetheineReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. long-chain-fatty-acid-CoA ligase (linolenate)
  3. (9Z,12Z,15Z)-octadecatrienoyl-CoA + H2O = S-(9Z,12Z,15Z-octadecatrienoyl)-4'-phosphopantetheine + adenosine 3',5'-bisphosphate + 2 H(+)

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

• S-(9Z,12Z-octadecadienoyl)-4'-phosphopantetheineReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. long-chain-fatty-acid-CoA ligase ((6Z,9Z)-octadecadienoic acid)
  3. (9Z,12Z)-octadecadienoyl-CoA + H2O = S-(9Z,12Z-octadecadienoyl)-4'-phosphopantetheine + adenosine 3',5'-bisphosphate + 2 H(+)

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

• S-(9Z-hexadecenoyl)-4'-phosphopantetheineReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. long-chain-fatty-acid-CoA ligase (palmitolate)
  3. (9Z)-hexadecenoyl-CoA + H2O = S-(9Z-hexadecenoyl)-4'-phosphopantetheine + adenosine 3',5'-bisphosphate + 2 H(+)

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

• itaconateReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. Itaconate:CoA ligase (GDP-forming)
  3. Itaconate:CoA ligase (GDP-forming)

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

• N-octadecanoyl-heptadecasphing-4-enineReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. long-chain-fatty-acid-CoA ligase (stearate)
  3. heptadecasphing-4-enine + octadecanoyl-CoA = N-octadecanoyl-heptadecasphing-4-enine + CoA + H(+)

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

• dehydroascorbic acidReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. 11-peroxy-docosahexaenoate to DHA conversion
  3. ascorbate to dehydroascorbic acid conversion

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

• linoleic 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 15 routes

• a monoacylglycerolReach from here →
  1. Lecithin Retinol Acyltransferase (11-Cis)
  2. an all-trans-retinyl ester + H2O = 11-cis-retinol + a fatty acid + H(+)
  3. a monoacylglycerol + H2O = glycerol + a fatty acid + H(+)

  Catalysed by RPE65, LIPEcytosolOne of 2 routes

• 1-(alk-1-enyl)-2-acyl-sn-glycero-3-phosphoethanolamineReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. acyl-CoA:sphingosine N-acyltransferase
  3. Acyl-CoA:1-alkenylglycerophosphoethanolamine O-acyltransferase

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

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

  Catalysed by DGAT1, LRAT, AWAT1, AWAT2 and 3 morecytosol, peroxisomeOne of 14 routes

• AH2Reach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. bile acid-CoA:amino acid N-acyltransferase (taurodeoxycholate)
  3. uridine(34) in tRNA + 5,10-methylenetetrahydrofolate + taurine + GTP + A + H2O = 5-taurinomethyluridine(34) in tRNA + 7,8-dihydrofolate + GDP + AH2 + phosphate + H(+)

  Catalysed by DGAT1, LRAT, AWAT1, AWAT2 and 3 morecytosolOne of 26 routes

• S-methyl-5'-thioadenosineReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. diamine N-acetyltransferase (N1-acetylspermidine)
  3. S-adenosylmethioninamine:spermidine 3-aminopropyltransferase

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

• 5-aminolevulinic acidReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. succinyl-CoA:glycine C-succinyltransferase (decarboxylating)

  Catalysed by DGAT1, LRAT, AWAT1, AWAT2 and 7 morecytosol, mitochondrial matrixOne of 2 routes

• hexadecanalReach 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. hexadecanoate + NADH + 2 H(+) = hexadecanal + NAD(+) + H2O

  Catalysed by RPE65, PNLIP, PNPLA4, LIPE and 3 more

• a sphingomyelinReach 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 4 routes

• Ala-tRNA(Ala)Reach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. L-Alanine:tRNA(Ala) ligase (AMP-forming)

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