an all-trans-retinyl ester

Three steps

• (9Z)-octadecenoyl-CoAReach from here →
  1. carboxylesterase (retinyl-ester)
  2. (10Z)-heptadecenoic acid formation
  3. (9Z)-octadecenoate + ATP + CoA = (9Z)-octadecenoyl-CoA + AMP + diphosphate

  Catalysed by CES2, RBP4, LIPF, LIPC and 24 morecytosol, extracellular space

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

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

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

  Catalysed by CES2, RBP4, LIPF, LIPC and 23 morecytosol, extracellular spaceOne of 21 routes

• prostaglandin H2Reach from here →
  1. carboxylesterase (retinyl-ester)
  2. (10Z)-heptadecenoic acid formation
  3. prostaglandin-endoperoxide synthase (arachidonate)

  Catalysed by CES2, RBP4, LIPF, LIPC and 18 morecytosol, extracellular spaceOne of 3 routes

• (12S)-hydroperoxy-(5Z,8Z,10E,14Z)-eicosatetraenoateReach from here →
  1. carboxylesterase (retinyl-ester)
  2. (10Z)-heptadecenoic acid formation
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + O2 = (12S)-hydroperoxy-(5Z,8Z,10E,14Z)-eicosatetraenoate

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

• (15S)-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoateReach from here →
  1. carboxylesterase (retinyl-ester)
  2. (10Z)-heptadecenoic acid formation
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + O2 = (15S)-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoate

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

• (5S)-hydroperoxy-(6E,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. carboxylesterase (retinyl-ester)
  2. (10Z)-heptadecenoic acid formation
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + O2 = (5S)-hydroperoxy-(6E,8Z,11Z,14Z)-eicosatetraenoate

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

• 7,8-dihydrofolateReach from here →
  1. carboxylesterase (retinyl-ester)
  2. all-trans-13,14-dihydroretinol + A = all-trans-retinol + AH2
  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 CES2, RBP4, LIPF, LIPC and 18 morecytosol

• leukotriene A4Reach from here →
  1. carboxylesterase (retinyl-ester)
  2. (10Z)-heptadecenoic acid formation
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + O2 = leukotriene A4 + H2O

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

• (13S)-hydroperoxy-(9Z,11E)-octadecadienoateReach from here →
  1. carboxylesterase (retinyl-ester)
  2. (10Z)-heptadecenoic acid formation
  3. Linoleate:oxygen 13-oxidoreductase

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

• (R)-2-hydroxyoctadecanoateReach from here →
  1. carboxylesterase (retinyl-ester)
  2. (10Z)-heptadecenoic acid formation
  3. octadecanoate + 2 Fe(II)-[cytochrome b5] + O2 + 2 H(+) = (R)-2-hydroxyoctadecanoate + 2 Fe(III)-[cytochrome b5] + H2O

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

• sphing-4-enineReach from here →
  1. all-trans-retinyl ester acylhydrolase, 11-cis-retinol forming
  2. Palmitoyl-CoA:retinol O-acyltransferase
  3. acyl-CoA:sphingosine N-acyltransferase

  Catalysed by RPE65, DGAT1, LRAT, AWAT1 and 6 morecytosol, Golgi apparatusOne of 2 routes

• sphinganineReach from here →
  1. carboxylesterase (retinyl-ester)
  2. N-acylsphingosine amidohydrolase
  3. an N-acylsphinganine + H2O = sphinganine + a fatty acid

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

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

  Catalysed by RPE65, DGAT1, LRAT, AWAT1 and 4 morecytosolOne of 3 routes

• L-methionineReach from here →
  1. all-trans-retinyl ester acylhydrolase, 11-cis-retinol forming
  2. Palmitoyl-CoA:retinol O-acyltransferase
  3. N-acetylglutamate synthase (N-acetylmethionine)

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

• L-alanineReach from here →
  1. all-trans-retinyl ester acylhydrolase, 11-cis-retinol forming
  2. Palmitoyl-CoA:retinol O-acyltransferase
  3. amino-acid N-acetyltransferase (N-acetyl-L-alanine)

  Catalysed by RPE65, DGAT1, LRAT, AWAT1 and 2 morecytosol, mitochondrial matrix

• L-asparagineReach from here →
  1. all-trans-retinyl ester acylhydrolase, 11-cis-retinol forming
  2. Palmitoyl-CoA:retinol O-acyltransferase
  3. N-acetylglutamate synthase (N-acetyl-L-asparagine)

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

• L,L-cystathionineReach from here →
  1. all-trans-retinyl ester acylhydrolase, 11-cis-retinol forming
  2. Palmitoyl-CoA:retinol O-acyltransferase
  3. N-acetylglutamate synthase (N-acetyl-L-cystathionine)

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

• an acyl-CoAReach from here →
  1. carboxylesterase (retinyl-ester)
  2. (10Z)-heptadecenoic acid formation
  3. acyl-CoA pool formation and breakdown

  Catalysed by CES2, RBP4, LIPF, LIPC and 16 morecytosol, extracellular spaceOne of 3 routes

• (3Z)-dodecenoyl-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-oxomyrist-5-enoyl-CoA)

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

• (25R)-3alpha,7alpha,12alpha-trihydroxy-5beta-cholestan-26-oyl-CoAReach from here →
  1. all-trans-retinyl ester acylhydrolase, 11-cis-retinol forming
  2. Palmitoyl-CoA:retinol O-acyltransferase
  3. 3alpha,7alpha,12alpha-trihydroxy-5beta-cholestanoate:CoA ligase (AMP-forming)

  Catalysed by RPE65, DGAT1, LRAT, AWAT1 and 4 morecytosol, endoplasmic reticulumOne of 3 routes

• deoxycholoyl-CoAReach from here →
  1. all-trans-retinyl ester acylhydrolase, 11-cis-retinol forming
  2. Palmitoyl-CoA:retinol O-acyltransferase
  3. cholate-CoA ligase (3alpha,12alpha-dihydroxy-5beta-cholanate)

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

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

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

• a 2,3-dehydroacyl-CoAReach from here →
  1. carboxylesterase (retinyl-ester)
  2. all-trans-13,14-dihydroretinol + A = all-trans-retinol + AH2
  3. a 2,3-saturated acyl-CoA + A = a 2,3-dehydroacyl-CoA + AH2

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

• (9S)-hydroperoxy-(10E,12Z)-octadecadienoateReach from here →
  1. carboxylesterase (retinyl-ester)
  2. (10Z)-heptadecenoic acid formation
  3. linoleate:oxygen 9-oxidoreductase

  Catalysed by CES2, RBP4, LIPF, LIPC and 16 morecytosol, extracellular space

• decanoyl-CoAReach from here →
  1. all-trans-retinyl ester acylhydrolase, 11-cis-retinol forming
  2. Palmitoyl-CoA:retinol O-acyltransferase
  3. medium-chain acyl-CoA ligase (decanoic acid)

  Catalysed by RPE65, DGAT1, LRAT, AWAT1 and 8 morecytosolOne of 7 routes

• (2E)-hexadecenoyl-CoAReach from here →
  1. carboxylesterase (retinyl-ester)
  2. (10Z)-heptadecenoic acid formation
  3. Long-Chain-Fatty-Acid-Coa Ligase

  Catalysed by CES2, RBP4, LIPF, LIPC and 23 morecytosol, extracellular space, endoplasmic reticulumOne of 6 routes

• (9Z)-hexadecenoyl-CoAReach from here →
  1. carboxylesterase (retinyl-ester)
  2. (10Z)-heptadecenoic acid formation
  3. long-chain-fatty-acid-CoA ligase (palmitolate)

  Catalysed by CES2, RBP4, LIPF, LIPC and 24 morecytosol, extracellular spaceOne of 16 routes

• Fe(II)-heme aReach from here →
  1. carboxylesterase (retinyl-ester)
  2. all-trans-13,14-dihydroretinol + A = all-trans-retinol + AH2
  3. Fe(II)-heme o + 2 A + H2O = Fe(II)-heme a + 2 AH2

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

• 3-hydroxyisovaleryl-CoAReach from here →
  1. all-trans-retinyl ester acylhydrolase, 11-cis-retinol forming
  2. Palmitoyl-CoA:retinol O-acyltransferase
  3. (3-Hydroxyisovalerylcoa->3-Hydroxyisovalerylcarnitine)

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

• CHEBI:63544Reach from here →
  1. carboxylesterase (retinyl-ester)
  2. (10Z)-heptadecenoic acid formation
  3. long-chain-fatty-acid-CoA ligase (adrenic acid)

  Catalysed by CES2, RBP4, LIPF, LIPC and 24 morecytosol, extracellular spaceOne of 9 routes

• 18-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. carboxylesterase (retinyl-ester)
  2. (10Z)-heptadecenoic acid formation
  3. cytochrome P450 (arachidonate)

  Catalysed by CES2, RBP4, LIPF, LIPC and 17 morecytosol, extracellular space, endoplasmic reticulumOne of 2 routes

• a 1,2-diacyl-sn-glycero-3-phosphoethanolamineReach 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 2-acyl-sn-glycero-3-phosphoethanolamine + a fatty acyl-CoA = a 1,2-diacyl-sn-glycero-3-phosphoethanolamine + CoA

  Catalysed by RPE65, ACSL3, LPGAT1

• a 1-acyl-sn-glycerolReach from here →
  1. an all-trans-retinyl ester + H2O = 11-cis-retinol + a fatty acid + H(+)
  2. a 1,3-diacyl-sn-glycerol + H2O = a 1-acyl-sn-glycerol + a fatty acid + H(+)
  3. a 1,3-diacyl-sn-glycerol + H2O = a 1-acyl-sn-glycerol + a fatty acid + H(+)

  Catalysed by RPE65, ABHD11

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

  Catalysed by CES2, RBP4, LIPF, LIPC and 24 morecytosol, extracellular spaceOne of 8 routes

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

  Catalysed by CES2, RBP4, LIPF, LIPC and 24 morecytosol, extracellular spaceOne of 16 routes

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

  Catalysed by CES2, RBP4, LIPF, LIPC and 24 morecytosol, extracellular spaceOne of 13 routes

• an N-acylsphinganine-1-phosphocholineReach from here →
  1. carboxylesterase (retinyl-ester)
  2. N-acylsphingosine amidohydrolase
  3. an N-acylsphinganine + a 1,2-diacyl-sn-glycero-3-phosphocholine = an N-acylsphinganine-1-phosphocholine + a 1,2-diacyl-sn-glycerol

  Catalysed by CES2, RBP4, LIPF, LIPC and 23 morecytosol

• Mo-molybdopterinReach from here →
  1. carboxylesterase (retinyl-ester)
  2. all-trans-13,14-dihydroretinol + A = all-trans-retinol + AH2
  3. Mo-molybdopterin + L-cysteine + AH2 = thio-Mo-molybdopterin + L-alanine + A + H2O

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

• (2E)-octadecenoyl-CoAReach from here →
  1. carboxylesterase (retinyl-ester)
  2. (10Z)-heptadecenoic acid formation
  3. fatty-acid-CoA ligase

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

• (6Z,9Z,12Z,15Z)-octadecatetraenoyl-CoAReach from here →
  1. all-trans-retinyl ester acylhydrolase, 11-cis-retinol forming
  2. Palmitoyl-CoA:retinol O-acyltransferase
  3. long-chain-fatty-acid-CoA ligase (stearidonic acid)

  Catalysed by RPE65, DGAT1, LRAT, AWAT1 and 10 morecytosolOne of 8 routes

• 1-(9Z-octadecenoyl)-sn-glycero-3-phospho-(1'-sn-glycerol)Reach from here →
  1. carboxylesterase (retinyl-ester)
  2. (10Z)-heptadecenoic acid formation
  3. 1-(9Z-octadecenoyl)-sn-glycero-3-phospho-(1'-sn-glycerol) + H2O = sn-glycero-3-phospho-(1'-sn-glycerol) + (9Z)-octadecenoate + H(+)

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

• 1-hexadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phospho-(1D-myo-inositol)Reach from here →
  1. carboxylesterase (retinyl-ester)
  2. (10Z)-heptadecenoic acid formation
  3. 1-hexadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phospho-(1D-myo-inositol) + H2O = 1-hexadecanoyl-sn-glycero-3-phospho-(1D-myo-inositol) + (9Z)-octadecenoate + H(+)

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

• N-dodecanoylsphing-4-enineReach from here →
  1. carboxylesterase (retinyl-ester)
  2. (10Z)-heptadecenoic acid formation
  3. N-dodecanoylsphing-4-enine + H2O = dodecanoate + sphing-4-enine

  Catalysed by CES2, RBP4, LIPF, LIPC and 20 morecytosol, extracellular space

• N-tetradecanoylsphing-4-enineReach from here →
  1. carboxylesterase (retinyl-ester)
  2. (10Z)-heptadecenoic acid formation
  3. N-tetradecanoylsphing-4-enine + H2O = sphing-4-enine + tetradecanoate

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

• N-octadecanoylsphing-4-enineReach from here →
  1. carboxylesterase (retinyl-ester)
  2. (10Z)-heptadecenoic acid formation
  3. N-octadecanoylsphing-4-enine + H2O = sphing-4-enine + octadecanoate

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

• 1,2-dihexadecanoyl-sn-glycero-3-phosphocholineReach from here →
  1. carboxylesterase (retinyl-ester)
  2. all-trans-retinol + 1,2-dihexadecanoyl-sn-glycero-3-phosphocholine = all-trans-retinyl hexadecanoate + 2-hexadecanoyl-sn-glycero-3-phosphocholine
  3. 2 2-hexadecanoyl-sn-glycero-3-phosphocholine = 1,2-dihexadecanoyl-sn-glycero-3-phosphocholine + sn-glycerol 3-phosphocholine

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

• (7Z,10Z,13Z,16Z)-docosatetraenoyl-CoAReach from here →
  1. carboxylesterase (retinyl-ester)
  2. (10Z)-heptadecenoic acid formation
  3. (7Z,10Z,13Z,16Z)-docosatetraenoate + ATP + CoA = (7Z,10Z,13Z,16Z)-docosatetraenoyl-CoA + AMP + diphosphate

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

• (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoAReach from here →
  1. carboxylesterase (retinyl-ester)
  2. (10Z)-heptadecenoic acid formation
  3. long-chain-fatty-acid-CoA ligase (EPA)

  Catalysed by CES2, RBP4, LIPF, LIPC and 24 morecytosol, extracellular spaceOne of 12 routes

• (7Z,10Z,13Z,16Z,19Z)-docosapentaenoyl-CoAReach from here →
  1. carboxylesterase (retinyl-ester)
  2. (10Z)-heptadecenoic acid formation
  3. long-chain-fatty-acid-CoA ligase (DPA)

  Catalysed by CES2, RBP4, LIPF, LIPC and 24 morecytosol, extracellular spaceOne of 8 routes