11-cis-retinyl hexadecanoate

Three steps

• (15Z)-tetracosenoateReach from here →
  1. 11-peroxy-docosahexaenoate to DHA conversion
  2. (10Z)-heptadecenoic acid formation
  3. (10Z)-heptadecenoic acid formation

  No catalyst recordedcytosol, extracellular spaceOne of 12 routes

• (5Z,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. 11-peroxy-docosahexaenoate to DHA conversion
  2. (10Z)-heptadecenoic acid formation
  3. (10Z)-heptadecenoic acid formation

  No catalyst recordedcytosol, extracellular spaceOne of 12 routes

• (11Z)-eicosenoateReach from here →
  1. 11-peroxy-docosahexaenoate to DHA conversion
  2. (10Z)-heptadecenoic acid formation
  3. (10Z)-heptadecenoic acid formation

  No catalyst recordedcytosol, extracellular spaceOne of 12 routes

• a 1-O-alkyl-2-acyl-sn-glycero-3-phosphocholineReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. acyl-CoA pool formation and breakdown
  3. Acyl-CoA:1-alkyl-sn-glycero-3-phosphocholine O-acyltransferase

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

• all-trans-4-oxoretinolReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. all-trans-Retinol 11-cis-trans-isomerase
  3. cytochrome P450 (retinol)

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

• 13-cis-retinalReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. 11-cis-retinol = 13-cis-retinol
  3. retinol dehydrogenase (13-cis-retinal)

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

• a 1,3-diacylglycerolReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. acyl-CoA pool formation and breakdown
  3. a 1-acylglycerol + an acyl-CoA = a 1,3-diacylglycerol + CoA

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

• a 1,2-diacylglycerolReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. acyl-CoA pool formation and breakdown
  3. a 2-acylglycerol + an acyl-CoA = a 1,2-diacylglycerol + CoA

  Catalysed by DGAT1, LRAT, AWAT1, AWAT2 and 6 morecytosolOne of 2 routes

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

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

• all-trans-13,14-dihydroretinolReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. all-trans-Retinol 11-cis-trans-isomerase
  3. all-trans-13,14-dihydroretinol + A = all-trans-retinol + AH2

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

• 16-hydroxyhexadecanoateReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. Palmitoyl-CoA hydrolase
  3. Fatty Acid Omega Oxidation (C16->W-Ohc16), Endoplasmatic Reticulum

  Catalysed by DGAT1, LRAT, AWAT1, AWAT2 and 8 morecytosol, endoplasmic reticulumOne of 2 routes

• a 1,2-diacyl-sn-glycero-3-phospho-L-serineReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. acyl-CoA pool formation and breakdown
  3. a 1-acyl-sn-glycero-3-phospho-L-serine + an acyl-CoA = a 1,2-diacyl-sn-glycero-3-phospho-L-serine + CoA

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

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

  Catalysed by DGAT1, LRAT, AWAT1, AWAT2 and 4 morecytosol, mitochondrial matrixOne of 10 routes

• (R)-methylmalonyl-CoAReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. Palmitoyl-CoA:retinol O-acyltransferase
  3. aldehyde dehydrogenase (2-methyl-3-oxopropanoate)

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

• (S)-methylmalonyl-CoAReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. Palmitoyl-CoA:retinol O-acyltransferase
  3. (S)-methylmalonyl-CoA hydrolase

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

• 3'-dephospho-CoAReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. Palmitoyl-CoA:retinol O-acyltransferase
  3. acid phosphatase 2, lysosomal (CoA)

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

• (2E)-dodecenoyl-CoAReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. Palmitoyl-CoA:retinol O-acyltransferase
  3. (2E)-dodecenoyl-CoA formation

  Catalysed by DGAT1, LRAT, AWAT1, AWAT2 and 1 morecytosol, mitochondrial matrixOne of 3 routes

• 3-oxohexadecanoyl-CoAReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. Fatty Acid Beta Oxidation (C16->C14), Mitochondrial
  3. tetradecanoyl-CoA + malonyl-CoA + H(+) = 3-oxohexadecanoyl-CoA + CO2 + CoA

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

• 4,8,12-trimethyltridecanoyl-CoAReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. Palmitoyl-CoA:retinol O-acyltransferase
  3. propanoyl-CoA C-acyltransferase (3-ketopristanoyl-CoA)

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

• (6Z,9Z,12Z)-octadecatrienoyl-CoAReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. Palmitoyl-CoA:retinol O-acyltransferase
  3. long-chain-fatty-acid-CoA ligase (gamma-linolenate)

  Catalysed by DGAT1, LRAT, AWAT1, AWAT2 and 9 morecytosolOne of 8 routes

• butanoyl-CoAReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. Palmitoyl-CoA:retinol O-acyltransferase
  3. Butanoate:CoA ligase (AMP-forming)

  Catalysed by DGAT1, LRAT, AWAT1, AWAT2 and 7 morecytosolOne of 9 routes

• dodecanoyl-CoAReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. Palmitoyl-CoA:retinol O-acyltransferase
  3. long-chain-fatty-acid-CoA ligase (lauric acid)

  Catalysed by DGAT1, LRAT, AWAT1, AWAT2 and 9 morecytosolOne of 12 routes

• glutaryl-CoAReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. Palmitoyl-CoA:retinol O-acyltransferase
  3. Production of Glutaryl Carnitine

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

• hexadecanoyl-CoAReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. palmitoyl-CoA desaturase (N-C16:0CoA -> N-C16:1CoA)
  3. hexadecanoyl-CoA + 2 Fe(II)-[cytochrome b5] + O2 + 2 H(+) = (9Z)-hexadecenoyl-CoA + 2 Fe(III)-[cytochrome b5] + 2 H2O

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

• eicosanoyl-CoAReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. Palmitoyl-CoA:retinol O-acyltransferase
  3. long-chain-fatty-acid-CoA ligase (eicosanoate)

  Catalysed by DGAT1, LRAT, AWAT1, AWAT2 and 9 morecytosolOne of 13 routes

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

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

• (9Z,12Z)-octadecadienoyl-CoAReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. Palmitoyl-CoA:retinol O-acyltransferase
  3. long-chain-fatty-acid-CoA ligase ((6Z,9Z)-octadecadienoic acid)

  Catalysed by DGAT1, LRAT, AWAT1, AWAT2 and 9 morecytosolOne of 14 routes

• (9Z)-octadecenoyl-CoAReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. fatty-acyl-CoA synthase (N-C18:0CoA)
  3. octadecanoyl-CoA + 2 Fe(II)-[cytochrome b5] + O2 + 2 H(+) = (9Z)-octadecenoyl-CoA + 2 Fe(III)-[cytochrome b5] + 2 H2O

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

• phytanoyl-CoAReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. Palmitoyl-CoA:retinol O-acyltransferase
  3. phytanate-CoA ligase

  Catalysed by DGAT1, LRAT, AWAT1, AWAT2 and 1 morecytosolOne of 5 routes

• 7,8-dihydrofolateReach from here →
  1. 11-peroxy-docosahexaenoate to DHA conversion
  2. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoate + AH2 + O2 = 17R-hydroxy-(4Z,7Z,10Z,13Z,15E,19Z)-docosahexaenoate + A + H2O
  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 PTGS2, MTO1cytosol

• a 1-acylglycerone 3-phosphateReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. glyceronephosphate O-acyltransferase (DHAP)
  3. 1-hexadecanoylglycerone 3-phosphate + a long-chain fatty acid = a 1-acylglycerone 3-phosphate + hexadecanoate

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

• sn-glycerol 3-phosphateReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. glycerol-3-phosphate 1-O-acyltransferase (palmitoyl-CoA)
  3. 1-hexadecanoyl-sn-glycero-3-phosphate + H2O = sn-glycerol 3-phosphate + hexadecanoate + H(+)

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

• a 1,2-diacyl-sn-glycero-3-phosphocholineReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. acyl-CoA pool formation and breakdown
  3. a 2-acyl-sn-glycero-3-phosphocholine + an acyl-CoA = a 1,2-diacyl-sn-glycero-3-phosphocholine + CoA

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

• an N-acylglycineReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. acyl-CoA pool formation and breakdown
  3. an acyl-CoA + glycine = an N-acylglycine + CoA + H(+)

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

• sphing-4-enineReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. Palmitoyl-CoA:retinol O-acyltransferase
  3. acyl-CoA:sphingosine N-acyltransferase

  Catalysed by DGAT1, LRAT, AWAT1, AWAT2 and 5 morecytosol, Golgi apparatusOne of 2 routes

• sphinganineReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. Palmitoyl-CoA:L-serine C-palmitoyltransferase (decarboxylating)
  3. sphinganine + NADP(+) = 3-oxosphinganine + NADPH + H(+)

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

• spermidineReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. Palmitoyl-CoA:retinol O-acyltransferase
  3. diamine N-acetyltransferase (N1-acetylspermidine)

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

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

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

• a 1,2-diacyl-sn-glycero-3-phospho-(1D-myo-inositol)Reach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. acyl-CoA pool formation and breakdown
  3. a 1-acyl-sn-glycero-3-phospho-(1D-myo-inositol) + an acyl-CoA = a 1,2-diacyl-sn-glycero-3-phospho-(1D-myo-inositol) + CoA

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

• a 1-acyl-sn-glycero-3-phosphateReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. acyl-CoA pool formation and breakdown
  3. sn-glycerol 3-phosphate + an acyl-CoA = a 1-acyl-sn-glycero-3-phosphate + CoA

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

• L-alanineReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. Palmitoyl-CoA:retinol O-acyltransferase
  3. amino-acid N-acetyltransferase (N-acetyl-L-alanine)

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

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

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

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

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

• glutathione disulfideReach from here →
  1. 11-peroxy-docosahexaenoate to DHA conversion
  2. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoate + O2 = (17S)-hydroperoxy-(4Z,7Z,10Z,13Z,15E,19Z)-docosahexaenoate
  3. (17S)-hydroperoxy-(4Z,7Z,10Z,13Z,15E,19Z)-docosahexaenoate + 2 glutathione = (17S)-hydroxy-(4Z,7Z,10Z,13Z,15E,19Z)-docosahexaenoate + glutathione disulfide + H2O

  Catalysed by ALOX5, ALOX15, GPX1, GPX4cytosolOne of 2 routes

• (3Z)-dodecenoyl-CoAReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. Palmitoyl-CoA:retinol O-acyltransferase
  3. acetyl-CoA C-acyltransferase (3-oxomyrist-5-enoyl-CoA)

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

• (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoateReach from here →
  1. 11-peroxy-docosahexaenoate to DHA conversion
  2. (10Z)-heptadecenoic acid formation
  3. (10Z)-heptadecenoic acid formation

  No catalyst recordedcytosol, extracellular spaceOne of 12 routes

• a 1,2-diacyl-sn-glycero-3-phosphateReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. acyl-CoA pool formation and breakdown
  3. a 1-acyl-sn-glycero-3-phosphate + an acyl-CoA = a 1,2-diacyl-sn-glycero-3-phosphate + CoA

  Catalysed by DGAT1, LRAT, AWAT1, AWAT2 and 14 morecytosol

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

  Catalysed by DGAT1, LRAT, AWAT1, AWAT2 and 3 morecytosol, endoplasmic reticulumOne of 3 routes

• deoxycholoyl-CoAReach from here →
  1. Palmitoyl-CoA:retinol O-acyltransferase
  2. Palmitoyl-CoA:retinol O-acyltransferase
  3. cholate-CoA ligase (3alpha,12alpha-dihydroxy-5beta-cholanate)

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

• a 2,3-dehydroacyl-CoAReach from here →
  1. 11-peroxy-docosahexaenoate to DHA conversion
  2. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoate + AH2 + O2 = 17R-hydroxy-(4Z,7Z,10Z,13Z,15E,19Z)-docosahexaenoate + A + H2O
  3. a 2,3-saturated acyl-CoA + A = a 2,3-dehydroacyl-CoA + AH2

  Catalysed by PTGS2, ACAD10cytosol