an all-trans-retinyl ester

Three steps

• 13-cis-retinyl hexadecanoateReach from here →
  1. carboxylesterase (retinyl-ester)
  2. retinol binding protein (retinol)
  3. 13-cis-retinol + hexadecanoyl-CoA = 13-cis-retinyl hexadecanoate + CoA

  Catalysed by CES2, RBP4, LIPF, LIPC and 19 morecytosol

• 9-cis-retinyl hexadecanoateReach from here →
  1. carboxylesterase (retinyl-ester)
  2. retinol binding protein (retinol)
  3. 9-cis-retinol + hexadecanoyl-CoA = 9-cis-retinyl hexadecanoate + CoA

  Catalysed by CES2, RBP4, LIPF, LIPC and 19 morecytosol

• all-trans-4-hydroxyretinalReach from here →
  1. carboxylesterase (retinyl-ester)
  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 CES2, RBP4, LIPF, LIPC and 18 morecytosolOne of 2 routes

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

• a 2-acyl-6-alpha-D-glucosaminyl-1-(1,2-diacyl-sn-glycero-3-phospho)-1D-myo-inositolReach from here →
  1. an all-trans-retinyl ester + H2O = 11-cis-retinol + a fatty acid + H(+)
  2. a fatty acid + ATP + CoA = a fatty acyl-CoA + AMP + diphosphate
  3. a 6-(alpha-D-glucosaminyl)-1-(1,2-diacyl-sn-glycero-3-phospho)-1D-myo-inositol + a fatty acyl-CoA = a 2-acyl-6-alpha-D-glucosaminyl-1-(1,2-diacyl-sn-glycero-3-phospho)-1D-myo-inositol + CoA

  Catalysed by RPE65, ACSL3, PIGW

• 8-hydroperoxy-(5Z,9E,11Z,14Z)-eicosatetraenoateReach from here →
  1. carboxylesterase (retinyl-ester)
  2. (10Z)-heptadecenoic acid formation
  3. arachidonate to 8-peroxy-(5Z,9E,11Z,14Z)-eicosatetraenoate conversion

  Catalysed by CES2, RBP4, LIPF, LIPC and 16 morecytosol, extracellular spaceOne of 2 routes

• 1,2,3-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-glycerolReach from here →
  1. carboxylesterase (retinyl-ester)
  2. (10Z)-heptadecenoic acid formation
  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 CES2, RBP4, LIPF, LIPC and 16 morecytosol, extracellular space

• N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-serineReach from here →
  1. carboxylesterase (retinyl-ester)
  2. (10Z)-heptadecenoic acid formation
  3. N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-serine + H2O = (5Z,8Z,11Z,14Z)-eicosatetraenoate + L-serine

  Catalysed by CES2, RBP4, LIPF, LIPC and 18 morecytosol, extracellular space

• an N-(fatty acyl)-glycineReach from here →
  1. an all-trans-retinyl ester + H2O = 11-cis-retinol + a fatty acid + H(+)
  2. a fatty acid + ATP + CoA = a fatty acyl-CoA + AMP + diphosphate
  3. a fatty acyl-CoA + glycine = an N-(fatty acyl)-glycine + CoA + H(+)

  Catalysed by RPE65, ACSL3, GLYATL2

• (7Z)-octadecenoyl-CoAReach from here →
  1. all-trans-retinyl ester acylhydrolase, 11-cis-retinol forming
  2. Palmitoyl-CoA:retinol O-acyltransferase
  3. carnitine O-palmitoyltransferase ((7Z)-octadecenoyl-CoA)

  Catalysed by RPE65, DGAT1, LRAT, AWAT1 and 5 morecytosolOne of 3 routes

• CHEBI:15345Reach from here →
  1. all-trans-retinyl ester acylhydrolase, 11-cis-retinol forming
  2. Palmitoyl-CoA:retinol O-acyltransferase
  3. Acetoacetate:CoA ligase (AMP-forming)

  Catalysed by RPE65, DGAT1, LRAT, AWAT1 and 3 morecytosolOne of 2 routes

• cholineReach from here →
  1. all-trans-retinyl ester acylhydrolase, 11-cis-retinol forming
  2. Palmitoyl-CoA:retinol O-acyltransferase
  3. Acetyl-CoA:choline O-acetyltransferase

  Catalysed by RPE65, DGAT1, LRAT, AWAT1 and 3 morecytosol, nucleus

• all-trans-retinoic acidReach from here →
  1. carboxylesterase (retinyl-ester)
  2. retinol: NADP+ oxidoreductase
  3. retinal:NAD+ oxidoreductase

  Catalysed by CES2, RBP4, LIPF, LIPC and 25 morecytosolOne of 3 routes

• CHEBI:15380Reach from here →
  1. all-trans-retinyl ester acylhydrolase, 11-cis-retinol forming
  2. Palmitoyl-CoA:retinol O-acyltransferase
  3. 5-aminolevulinate synthase (2-amino-3-oxoadipate)

  Catalysed by RPE65, DGAT1, LRAT, AWAT1 and 4 morecytosol, mitochondrial matrixOne of 8 routes

• CHEBI:15477Reach from here →
  1. all-trans-retinyl ester acylhydrolase, 11-cis-retinol forming
  2. Palmitoyl-CoA:retinol O-acyltransferase
  3. glycine N-acyltransferase (2-methylbutyryl-CoA)

  Catalysed by RPE65, DGAT1, LRAT, AWAT1 and 5 morecytosol, mitochondrial matrixOne of 2 routes

• 2-methylcrotonoyl-CoAReach from here →
  1. all-trans-retinyl ester acylhydrolase, 11-cis-retinol forming
  2. Palmitoyl-CoA:retinol O-acyltransferase
  3. Production of Tiglylcarnitine

  Catalysed by RPE65, DGAT1, LRAT, AWAT1 and 4 morecytosolOne of 2 routes

• isobutyryl-CoAReach from here →
  1. all-trans-retinyl ester acylhydrolase, 11-cis-retinol forming
  2. Palmitoyl-CoA:retinol O-acyltransferase
  3. acetyl-CoA C-acyltransferase (3-oxo-4-methyl-pentanoyl-CoA)

  Catalysed by RPE65, DGAT1, LRAT, AWAT1 and 5 morecytosol, mitochondrial matrixOne of 3 routes

• 3-methylbut-2-enoyl-CoAReach from here →
  1. all-trans-retinyl ester acylhydrolase, 11-cis-retinol forming
  2. Palmitoyl-CoA:retinol O-acyltransferase
  3. glycine-N-acyltransferase (3-methylcrotonoylglycine)

  Catalysed by RPE65, DGAT1, LRAT, AWAT1 and 3 morecytosol, mitochondrial matrix

• isovaleryl-CoAReach from here →
  1. all-trans-retinyl ester acylhydrolase, 11-cis-retinol forming
  2. Palmitoyl-CoA:retinol O-acyltransferase
  3. glycine N-acyltransferase (isovalerylglycine)

  Catalysed by RPE65, DGAT1, LRAT, AWAT1 and 5 morecytosol, mitochondrial matrixOne of 3 routes

• arachidonoyl-CoAReach from here →
  1. carboxylesterase (retinyl-ester)
  2. (10Z)-heptadecenoic acid formation
  3. Arachidonate:CoA ligase (AMP-forming)

  Catalysed by CES2, RBP4, LIPF, LIPC and 24 morecytosol, extracellular spaceOne of 14 routes

• CHEBI:15519Reach from here →
  1. all-trans-retinyl ester acylhydrolase, 11-cis-retinol forming
  2. Palmitoyl-CoA:retinol O-acyltransferase
  3. propanoyl-CoA C-acyltransferase

  Catalysed by RPE65, DGAT1, LRAT, AWAT1 and 5 morecytosol, peroxisomeOne of 2 routes

• palmitoyl-CoAReach from here →
  1. carboxylesterase (retinyl-ester)
  2. (10Z)-heptadecenoic acid formation
  3. Palmitate:CoA ligase (AMP-forming)

  Catalysed by CES2, RBP4, LIPF, LIPC and 24 morecytosol, extracellular spaceOne of 15 routes

• oleoyl-CoAReach from here →
  1. carboxylesterase (retinyl-ester)
  2. (10Z)-heptadecenoic acid formation
  3. long-chain-fatty-acid-CoA ligase (oleate)

  Catalysed by CES2, RBP4, LIPF, LIPC and 24 morecytosol, extracellular spaceOne of 14 routes

• phenylacetyl-CoAReach from here →
  1. all-trans-retinyl ester acylhydrolase, 11-cis-retinol forming
  2. Palmitoyl-CoA:retinol O-acyltransferase
  3. Phenylacetate:CoA ligase

  Catalysed by RPE65, DGAT1, LRAT, AWAT1 and 2 morecytosolOne of 3 routes

• propionyl-CoAReach from here →
  1. all-trans-retinyl ester acylhydrolase, 11-cis-retinol forming
  2. Palmitoyl-CoA:retinol O-acyltransferase
  3. Propanoate:CoA ligase (AMP-forming)

  Catalysed by RPE65, DGAT1, LRAT, AWAT1 and 5 morecytosolOne of 43 routes

• (7S)-hydroperoxy-(4Z,8E,10Z,13Z,16Z,19Z)-docosahexaenoateReach from here →
  1. carboxylesterase (retinyl-ester)
  2. (10Z)-heptadecenoic acid formation
  3. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoate + O2 = (7S)-hydroperoxy-(4Z,8E,10Z,13Z,16Z,19Z)-docosahexaenoate

  Catalysed by CES2, RBP4, LIPF, LIPC and 17 morecytosol, extracellular space

• (11S)-hydroperoxy-(4Z,7Z,9E,13Z,16Z,19Z)-docosahexaenoateReach from here →
  1. carboxylesterase (retinyl-ester)
  2. (10Z)-heptadecenoic acid formation
  3. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoate + O2 = (11S)-hydroperoxy-(4Z,7Z,9E,13Z,16Z,19Z)-docosahexaenoate

  Catalysed by CES2, RBP4, LIPF, LIPC and 17 morecytosol, extracellular space

• 12(S)-HPETEReach from here →
  1. carboxylesterase (retinyl-ester)
  2. (10Z)-heptadecenoic acid formation
  3. arachidonate:oxygen 12-oxidoreductase

  Catalysed by CES2, RBP4, LIPF, LIPC and 17 morecytosol, extracellular spaceOne of 4 routes

• 15(S)-HPETEReach from here →
  1. carboxylesterase (retinyl-ester)
  2. (10Z)-heptadecenoic acid formation
  3. arachidonate:oxygen 15-oxidoreductase

  Catalysed by CES2, RBP4, LIPF, LIPC and 18 morecytosol, extracellular spaceOne of 4 routes

• 5(S)-HPETEReach from here →
  1. carboxylesterase (retinyl-ester)
  2. (10Z)-heptadecenoic acid formation
  3. Arachidonate:oxygen 5-oxidoreductase

  Catalysed by CES2, RBP4, LIPF, LIPC and 17 morecytosol, extracellular space

• CHEBI:15650Reach from here →
  1. all-trans-retinyl ester acylhydrolase, 11-cis-retinol forming
  2. Palmitoyl-CoA:retinol O-acyltransferase
  3. N-acetyl-LTE4 to leukotriene E4 conversion

  Catalysed by RPE65, DGAT1, LRAT, AWAT1 and 34 morecytosolOne of 2 routes

• betaine aldehydeReach from here →
  1. carboxylesterase (retinyl-ester)
  2. all-trans-13,14-dihydroretinol + A = all-trans-retinol + AH2
  3. choline + A = betaine aldehyde + AH2

  Catalysed by CES2, RBP4, LIPF, LIPC and 18 morecytosol

• CHEBI:15727Reach from here →
  1. all-trans-retinyl ester acylhydrolase, 11-cis-retinol forming
  2. Palmitoyl-CoA:retinol O-acyltransferase
  3. N-alpha-acetyltransferase 10, NatA catalytic subunit (acetylcarnosine)

  Catalysed by RPE65, DGAT1, LRAT, AWAT1 and 3 morecytosol

• CHEBI:15746Reach from here →
  1. all-trans-retinyl ester acylhydrolase, 11-cis-retinol forming
  2. Palmitoyl-CoA:retinol O-acyltransferase
  3. diamine N-acetyltransferase (N1-acetylspermine)

  Catalysed by RPE65, DGAT1, LRAT, AWAT1 and 4 morecytosolOne of 2 routes

• 1,2-diacyl-sn-glycero-3-phosphocholine(1+)Reach from here →
  1. carboxylesterase (retinyl-ester)
  2. Lecithin Retinol Acyltransferase
  3. Acyl-CoA:1-acyl-sn-glycero-3-phosphocholine O-acyltransferase

  Catalysed by CES2, RBP4, LIPF, LIPC and 21 morecytosol

• oxaloacetateReach from here →
  1. carboxylesterase (retinyl-ester)
  2. all-trans-13,14-dihydroretinol + A = all-trans-retinol + AH2
  3. (R)-malate + A = oxaloacetate + AH2

  Catalysed by CES2, RBP4, LIPF, LIPC and 18 morecytosolOne of 2 routes

• CHEBI:16566Reach from here →
  1. carboxylesterase (retinyl-ester)
  2. N-acylsphingosine amidohydrolase
  3. N-acylsphingosine amidohydrolase

  Catalysed by CES2, RBP4, LIPF, LIPC and 21 morecytosol

• 8-hydroxydodecanoateReach from here →
  1. carboxylesterase (retinyl-ester)
  2. (10Z)-heptadecenoic acid formation
  3. dodecanoate + reduced [NADPH--hemoprotein reductase] + O2 = 8-hydroxydodecanoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by CES2, RBP4, LIPF, LIPC and 17 morecytosol, extracellular space

• 10-hydroxydodecanoateReach from here →
  1. carboxylesterase (retinyl-ester)
  2. (10Z)-heptadecenoic acid formation
  3. dodecanoate + reduced [NADPH--hemoprotein reductase] + O2 = 10-hydroxydodecanoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by CES2, RBP4, LIPF, LIPC and 17 morecytosol, extracellular space

• 9-hydroxydodecanoateReach from here →
  1. carboxylesterase (retinyl-ester)
  2. (10Z)-heptadecenoic acid formation
  3. dodecanoate + reduced [NADPH--hemoprotein reductase] + O2 = 9-hydroxydodecanoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by CES2, RBP4, LIPF, LIPC and 17 morecytosol, extracellular space

• 9-hydroxytetradecanoateReach from here →
  1. carboxylesterase (retinyl-ester)
  2. (10Z)-heptadecenoic acid formation
  3. tetradecanoate + reduced [NADPH--hemoprotein reductase] + O2 = 9-hydroxytetradecanoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by CES2, RBP4, LIPF, LIPC and 17 morecytosol, extracellular space

• 10-hydroxytetradecanoateReach from here →
  1. carboxylesterase (retinyl-ester)
  2. (10Z)-heptadecenoic acid formation
  3. tetradecanoate + reduced [NADPH--hemoprotein reductase] + O2 = 10-hydroxytetradecanoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by CES2, RBP4, LIPF, LIPC and 17 morecytosol, extracellular space

• 12-hydroxytetradecanoateReach from here →
  1. carboxylesterase (retinyl-ester)
  2. (10Z)-heptadecenoic acid formation
  3. tetradecanoate + reduced [NADPH--hemoprotein reductase] + O2 = 12-hydroxytetradecanoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by CES2, RBP4, LIPF, LIPC and 17 morecytosol, extracellular space

• 11-hydroxytetradecanoateReach from here →
  1. carboxylesterase (retinyl-ester)
  2. (10Z)-heptadecenoic acid formation
  3. tetradecanoate + reduced [NADPH--hemoprotein reductase] + O2 = 11-hydroxytetradecanoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by CES2, RBP4, LIPF, LIPC and 17 morecytosol, extracellular space

• formaldehydeReach from here →
  1. carboxylesterase (retinyl-ester)
  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 CES2, RBP4, LIPF, LIPC and 19 morecytosolOne of 3 routes

• CHEBI:16856Reach from here →
  1. carboxylesterase (retinyl-ester)
  2. (10Z)-heptadecenoic acid formation
  3. transport of arachidonate and GSH (cytosol to extracellular)

  Catalysed by CES2, RBP4, LIPF, LIPC and 16 morecytosol, extracellular spaceOne of 2 routes

• sn-glycerol 3-phosphocholineReach from here →
  1. carboxylesterase (retinyl-ester)
  2. Lecithin Retinol Acyltransferase
  3. 1-Acyl-sn-glycero-3-phosphocholine acylhydrolase

  Catalysed by CES2, RBP4, LIPF, LIPC and 27 morecytosolOne of 3 routes

• 1-acyl-sn-glycerol 3-phosphateReach from here →
  1. an all-trans-retinyl ester + H2O = 11-cis-retinol + a fatty acid + H(+)
  2. a monoacylglycerol + H2O = glycerol + a fatty acid + H(+)
  3. ATP:acylglycerol 3-phosphotransferase

  Catalysed by RPE65, LIPE, AGKcytosolOne of 6 routes

• octadecanalReach from here →
  1. carboxylesterase (retinyl-ester)
  2. (10Z)-heptadecenoic acid formation
  3. octadecanal + NAD(+) + H2O = octadecanoate + NADH + 2 H(+)

  Catalysed by CES2, RBP4, LIPF, LIPC and 17 morecytosol, extracellular space

• anilineReach from here →
  1. all-trans-retinyl ester acylhydrolase, 11-cis-retinol forming
  2. Palmitoyl-CoA:retinol O-acyltransferase
  3. Acetyl-CoA:arylamine N-acetyltransferase

  Catalysed by RPE65, DGAT1, LRAT, AWAT1 and 4 morecytosol