an all-trans-retinyl ester

Three steps

• (14S)-hydroperoxy-(4Z,7Z,10Z,12E,16Z,19Z)-docosahexaenoateReach from here →
  1. carboxylesterase (retinyl-ester)
  2. (10Z)-heptadecenoic acid formation
  3. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoate + O2 = (14S)-hydroperoxy-(4Z,7Z,10Z,12E,16Z,19Z)-docosahexaenoate

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

• (5Z,7Z,8Z,10E,14Z,17Z)-12-hydroperoxyeicosapentaenoateReach from here →
  1. carboxylesterase (retinyl-ester)
  2. (10Z)-heptadecenoic acid formation
  3. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate + O2 = (5Z,7Z,8Z,10E,14Z,17Z)-12-hydroperoxyeicosapentaenoate

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

• 9-cis-retinalReach from here →
  1. carboxylesterase (retinyl-ester)
  2. retinol: NADP+ oxidoreductase
  3. retinol binding protein (retinal)

  Catalysed by CES2, RBP4, LIPF, LIPC and 24 morecytosol, endoplasmic reticulumOne of 6 routes

• 18-hydroxy-(9Z)-octadecenoateReach from here →
  1. carboxylesterase (retinyl-ester)
  2. (10Z)-heptadecenoic acid formation
  3. (9Z)-octadecenoate + reduced [NADPH--hemoprotein reductase] + O2 = 18-hydroxy-(9Z)-octadecenoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

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

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

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

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

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

• (11R)-hydroxy-(5Z,8Z,12E,14Z)-eicosatetraenoateReach from here →
  1. carboxylesterase (retinyl-ester)
  2. (10Z)-heptadecenoic acid formation
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + AH2 + O2 = (11R)-hydroxy-(5Z,8Z,12E,14Z)-eicosatetraenoate + A + H2O

  Catalysed by CES2, RBP4, LIPF, LIPC and 17 morecytosol, extracellular spaceOne of 2 routes

• (15R)-hydroxy-(5Z,8Z,11Z,13E)-eicosatetraenoateReach from here →
  1. carboxylesterase (retinyl-ester)
  2. (10Z)-heptadecenoic acid formation
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + AH2 + O2 = (15R)-hydroxy-(5Z,8Z,11Z,13E)-eicosatetraenoate + A + H2O

  Catalysed by CES2, RBP4, LIPF, LIPC and 17 morecytosol, extracellular spaceOne of 2 routes

• hexadecanoateReach from here →
  1. carboxylesterase (retinyl-ester)
  2. all-trans-retinol + hexadecanoyl-CoA = all-trans-retinyl hexadecanoate + CoA
  3. all-trans-retinyl hexadecanoate + H2O = all-trans-retinol + hexadecanoate + H(+)

  Catalysed by CES2, RBP4, LIPF, LIPC and 20 morecytosolOne of 3 routes

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

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

• 11R-hydroperoxy-(5Z,8Z,12E,14Z)-eicosatetraenoateReach from here →
  1. carboxylesterase (retinyl-ester)
  2. (10Z)-heptadecenoic acid formation
  3. Arachidonate: oxygen 11-oxidoreductase

  Catalysed by CES2, RBP4, LIPF, LIPC and 17 morecytosol, extracellular spaceOne of 2 routes

• prostaglandin G2Reach from here →
  1. carboxylesterase (retinyl-ester)
  2. (10Z)-heptadecenoic acid formation
  3. Arachidonate:oxygen oxidoreductase

  Catalysed by CES2, RBP4, LIPF, LIPC and 18 morecytosol, extracellular space, endoplasmic reticulumOne of 2 routes

• 14-hydroperoxy-(4Z,7Z,10Z,12E,16Z,19Z)-docosahexaenoateReach from here →
  1. carboxylesterase (retinyl-ester)
  2. (10Z)-heptadecenoic acid formation
  3. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoate + O2 = 14-hydroperoxy-(4Z,7Z,10Z,12E,16Z,19Z)-docosahexaenoate

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

• (12R)-hydroxy-(5Z,8Z,10E,14Z)-eicosatetraenoateReach from here →
  1. carboxylesterase (retinyl-ester)
  2. (10Z)-heptadecenoic acid formation
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + reduced [NADPH--hemoprotein reductase] + O2 = (12R)-hydroxy-(5Z,8Z,10E,14Z)-eicosatetraenoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

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

• 14,15-epoxy-(5Z,8Z,11Z)-eicosatrienoateReach from here →
  1. carboxylesterase (retinyl-ester)
  2. (10Z)-heptadecenoic acid formation
  3. unspecific monooxygenase (arachidonate)

  Catalysed by CES2, RBP4, LIPF, LIPC and 43 morecytosol, extracellular spaceOne of 4 routes

• 8,9-epoxy-(5Z,11Z,14Z)-eicosatrienoateReach from here →
  1. carboxylesterase (retinyl-ester)
  2. (10Z)-heptadecenoic acid formation
  3. unspecific monooxygenase (arachidonate)

  Catalysed by CES2, RBP4, LIPF, LIPC and 42 morecytosol, extracellular spaceOne of 3 routes

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

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

• 1-heptadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphoserineReach from here →
  1. carboxylesterase (retinyl-ester)
  2. (10Z)-heptadecenoic acid formation
  3. 1-heptadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphoserine + H2O = 1-heptadecanoyl-sn-glycero-3-phosphoserine + (5Z,8Z,11Z,14Z)-eicosatetraenoate + H(+)

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

• 1-heptadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholineReach from here →
  1. carboxylesterase (retinyl-ester)
  2. (10Z)-heptadecenoic acid formation
  3. 1-heptadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholine + H2O = 1-heptadecanoyl-sn-glycero-3-phosphocholine + (5Z,8Z,11Z,14Z)-eicosatetraenoate + H(+)

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

• 1-heptadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphoethanolamineReach from here →
  1. carboxylesterase (retinyl-ester)
  2. (10Z)-heptadecenoic acid formation
  3. 1-heptadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphoethanolamine + H2O = 1-heptadecanoyl-sn-glycero-3-phosphoethanolamine + (5Z,8Z,11Z,14Z)-eicosatetraenoate + H(+)

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

• (5Z)-tetradecenoyl-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 (physeteric acid)

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

• (3E)-decenoyl-CoAReach from here →
  1. all-trans-retinyl ester acylhydrolase, 11-cis-retinol forming
  2. Palmitoyl-CoA:retinol O-acyltransferase
  3. Fatty Acid Beta Oxidation (C12:1->C10:1), Mitochondrial

  Catalysed by RPE65, DGAT1, LRAT, AWAT1 and 6 morecytosol, mitochondrial matrix

• 7-hydroxydodecanoateReach from here →
  1. carboxylesterase (retinyl-ester)
  2. (10Z)-heptadecenoic acid formation
  3. dodecanoate + reduced [NADPH--hemoprotein reductase] + O2 = 7-hydroxydodecanoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

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

• N-(dodecanoyl)-sphinganineReach from here →
  1. carboxylesterase (retinyl-ester)
  2. (10Z)-heptadecenoic acid formation
  3. N-(dodecanoyl)-sphinganine + H2O = dodecanoate + sphinganine

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

• (2R,6)-dimethylheptanoyl-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(R),8-dimethyl-nonanoyl-CoA)

  Catalysed by RPE65, DGAT1, LRAT, AWAT1 and 5 morecytosol, mitochondrial matrix

• (7Z)-hexadecenoyl-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 (7-palmitoleic acid)

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

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

  Catalysed by CES2, RBP4, LIPF, LIPC and 24 morecytosol, extracellular spaceOne of 6 routes

• (12S)-hydroperoxy-(5Z,8Z,10E,14Z,17Z)-eicosapentaenoateReach from here →
  1. carboxylesterase (retinyl-ester)
  2. (10Z)-heptadecenoic acid formation
  3. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate + O2 = (12S)-hydroperoxy-(5Z,8Z,10E,14Z,17Z)-eicosapentaenoate

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

• (18R)-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. carboxylesterase (retinyl-ester)
  2. (10Z)-heptadecenoic acid formation
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + reduced [NADPH--hemoprotein reductase] + O2 = (18R)-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

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

• 17R-hydroxy-(4Z,7Z,10Z,13Z,15E,19Z)-docosahexaenoateReach from here →
  1. carboxylesterase (retinyl-ester)
  2. (10Z)-heptadecenoic acid formation
  3. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoate + AH2 + O2 = 17R-hydroxy-(4Z,7Z,10Z,13Z,15E,19Z)-docosahexaenoate + A + H2O

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

• 13-hydroxy-(4Z,7Z,10Z,14E,16Z,19Z)-docosahexaenoateReach from here →
  1. carboxylesterase (retinyl-ester)
  2. (10Z)-heptadecenoic acid formation
  3. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoate + AH2 + O2 = 13-hydroxy-(4Z,7Z,10Z,14E,16Z,19Z)-docosahexaenoate + A + H2O

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

• (18R)-hydroxy-(5Z,8Z,11Z,14Z,16E)-eicosapentaenoateReach from here →
  1. carboxylesterase (retinyl-ester)
  2. (10Z)-heptadecenoic acid formation
  3. prostaglandin-endoperoxide synthase (EPA)

  Catalysed by CES2, RBP4, LIPF, LIPC and 18 morecytosol, extracellular spaceOne of 2 routes

• (15R)-hydroxy-(5Z,8Z,11Z,13E,17Z)-eicosapentaenoateReach from here →
  1. carboxylesterase (retinyl-ester)
  2. (10Z)-heptadecenoic acid formation
  3. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate + AH2 + O2 = (15R)-hydroxy-(5Z,8Z,11Z,13E,17Z)-eicosapentaenoate + A + H2O

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

• (11R)-hydroxy-(5Z,8Z,12E,14Z,17Z)-eicosapentaenoateReach from here →
  1. carboxylesterase (retinyl-ester)
  2. (10Z)-heptadecenoic acid formation
  3. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate + AH2 + O2 = (11R)-hydroxy-(5Z,8Z,12E,14Z,17Z)-eicosapentaenoate + A + H2O

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

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

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

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

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

• 13R-hydroxy-(7Z,10Z,14E,16Z,19Z)-docosapentaenoateReach from here →
  1. carboxylesterase (retinyl-ester)
  2. (10Z)-heptadecenoic acid formation
  3. (7Z,10Z,13Z,16Z,19Z)-docosapentaenoate + AH2 + O2 = 13R-hydroxy-(7Z,10Z,14E,16Z,19Z)-docosapentaenoate + A + H2O

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