(2E)-octadecenoyl-CoA

Three steps

• (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoAReach from here →
  1. Carnitine O-Palmitoyltransferase
  2. long-chain-fatty-acid-CoA ligase (dihomo-gamma-linolenate)
  3. (8Z,11Z,14Z)-eicosatrienoyl-CoA + 2 Fe(II)-[cytochrome b5] + O2 + 2 H(+) = (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA + 2 Fe(III)-[cytochrome b5] + 2 H2O

  Catalysed by CPT1A, CPT1C, CPT1B, SLC27A2 and 8 morecytosol

• hexadecanoyl-CoAReach from here →
  1. Carnitine O-Palmitoyltransferase
  2. Carnitine O-Palmitoyltransferase
  3. (2E)-hexadecenoyl-CoA + NADPH + H(+) = hexadecanoyl-CoA + NADP(+)

  Catalysed by CPT1A, CPT1C, CPT1B, TECRcytosolOne of 2 routes

• propanoyl-CoAReach from here →
  1. Carnitine O-Palmitoyltransferase
  2. (S)-methylmalonyl-CoA hydrolase
  3. (S)-methylmalonyl-CoA + H(+) = propanoyl-CoA + CO2

  Catalysed by CPT1A, CPT1C, CPT1B, ECHDC1cytosol, mitochondrial matrix

• D-alanineReach from here →
  1. Carnitine O-Palmitoyltransferase
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. D-alanine(out) + L-alanine(in) = D-alanine(in) + L-alanine(out)

  Catalysed by CPT1A, CPT1C, CPT1B, SLC7A10cytosol, mitochondrial matrix, inner side of the membrane, outer side of the membraneOne of 2 routes

• sarcosineReach from here →
  1. Carnitine O-Palmitoyltransferase
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. sarcosine + O2 + H2O = formaldehyde + glycine + H2O2

  Catalysed by CPT1A, CPT1C, CPT1B, GLYAT and 3 morecytosol, mitochondrial matrixOne of 2 routes

• S-adenosyl 3-(methylsulfanyl)propylamineReach from here →
  1. Carnitine O-Palmitoyltransferase
  2. diamine N-acetyltransferase (N1-acetylspermidine)
  3. S-adenosyl 3-(methylsulfanyl)propylamine + putrescine = S-methyl-5'-thioadenosine + spermidine + H(+)

  Catalysed by CPT1A, CPT1C, CPT1B, SAT1 and 2 morecytosol

• 7,8-dihydrofolateReach from here →
  1. Carnitine O-Palmitoyltransferase
  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 CPT1A, CPT1C, CPT1B, BAAT and 1 morecytosol

• (6S)-5,6,7,8-tetrahydrofolateReach from here →
  1. Carnitine O-Palmitoyltransferase
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. (6R)-5,10-methylene-5,6,7,8-tetrahydrofolate + glycine + H2O = (6S)-5,6,7,8-tetrahydrofolate + L-serine

  Catalysed by CPT1A, CPT1C, CPT1B, GLYAT and 4 morecytosol, mitochondrial matrix

• (13S)-hydroperoxy-(9Z,11E)-octadecadienoateReach from here →
  1. fatty acyl-CoA desaturase (N-C18:1CoA -> N-C18:2CoA)
  2. Linoleoyl-CoA hydrolase
  3. Linoleate:oxygen 13-oxidoreductase

  Catalysed by FADS2, ACOT7, BAAT, THEM4 and 4 morecytosolOne of 2 routes

• propane-1,3-diamineReach from here →
  1. Carnitine O-Palmitoyltransferase
  2. diamine N-acetyltransferase (N1-acetylspermidine)
  3. [eIF5A protein]-L-lysine + spermidine = [eIF5A protein]-deoxyhypusine + propane-1,3-diamine

  Catalysed by CPT1A, CPT1C, CPT1B, SAT1 and 2 morecytosol

• 1-hexadecanoyl-sn-glycero-3-phosphateReach from here →
  1. Carnitine O-Palmitoyltransferase
  2. Palmitate:CoA ligase (AMP-forming)
  3. glycerol-3-phosphate 1-O-acyltransferase (palmitoyl-CoA)

  Catalysed by CPT1A, CPT1C, CPT1B, SLC27A2 and 11 morecytosol

• a 1-acylglycerone 3-phosphateReach from here →
  1. fatty acyl-CoA desaturase (N-C18:1CoA -> N-C18:2CoA)
  2. acyl-CoA pool formation and breakdown
  3. dihydroxyacetone phosphate + an acyl-CoA = a 1-acylglycerone 3-phosphate + CoA

  Catalysed by FADS2, GNPATcytosol

• (R)-2-hydroxyoctadecanoateReach from here →
  1. octadecanoyl-CoA:NADP+ trans-2-oxidoreductase
  2. Stearoyl-CoA hydrolase
  3. octadecanoate + 2 Fe(II)-[cytochrome b5] + O2 + 2 H(+) = (R)-2-hydroxyoctadecanoate + 2 Fe(III)-[cytochrome b5] + H2O

  Catalysed by TECRL, TECR, ACOT7, BAAT and 4 morecytosol

• O-acetyl-(R)-carnitineReach from here →
  1. Carnitine O-Palmitoyltransferase
  2. Carnitine O-Palmitoyltransferase
  3. Acetyl-CoA:carnitine O-acetyltransferase

  Catalysed by CPT1A, CPT1C, CPT1BcytosolOne of 9 routes

• ethanolamineReach from here →
  1. octadecanoyl-CoA:NADP+ trans-2-oxidoreductase
  2. 2-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamine + octadecanoyl-CoA = 1-octadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamine + CoA
  3. 1-octadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamine + L-serine = 1-octadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phospho-L-serine + ethanolamine

  Catalysed by TECRL, TECR, LPGAT1, PTDSS2cytosol

• a 1,2-diacyl-sn-glycero-3-phosphocholineReach from here →
  1. fatty acyl-CoA desaturase (N-C18:1CoA -> N-C18:2CoA)
  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 FADS2, LPGAT1cytosolOne of 2 routes

• an N-acylglycineReach from here →
  1. fatty acyl-CoA desaturase (N-C18:1CoA -> N-C18:2CoA)
  2. acyl-CoA pool formation and breakdown
  3. an acyl-CoA + glycine = an N-acylglycine + CoA + H(+)

  Catalysed by FADS2, GLYATL3, GLYAT, GLYATL2cytosolOne of 2 routes

• 2-oxo-3-sulfanylpropanoateReach from here →
  1. Carnitine O-Palmitoyltransferase
  2. N-acetylglutamate synthase (N-acetyl-L-cysteine)
  3. L-Cysteine:2-oxoglutarate aminotransferase

  Catalysed by CPT1A, CPT1C, CPT1B, NAGS and 2 morecytosol, mitochondrial matrixOne of 3 routes

• guanidinoacetateReach from here →
  1. Carnitine O-Palmitoyltransferase
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. L-Arginine:glycine amidinotransferase

  Catalysed by CPT1A, CPT1C, CPT1B, GLYAT and 3 morecytosol, mitochondrial matrixOne of 2 routes

• D-threonineReach from here →
  1. Carnitine O-Palmitoyltransferase
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. D-threonine(out) + L-alanine(in) = D-threonine(in) + L-alanine(out)

  Catalysed by CPT1A, CPT1C, CPT1B, SLC7A10cytosol, mitochondrial matrix, inner side of the membrane, outer side of the membraneOne of 2 routes

• sphinganineReach from here →
  1. octadecanoyl-CoA:NADP+ trans-2-oxidoreductase
  2. sphinganine + octadecanoyl-CoA = N-(octadecanoyl)-sphinganine + CoA + H(+)
  3. N-(octadecanoyl)-sphinganine + H2O = sphinganine + octadecanoate

  Catalysed by TECRL, TECR, CERS1, CERS6 and 5 morecytosol

• a 1,2-diacyl-sn-glycero-3-phospho-(1D-myo-inositol)Reach from here →
  1. fatty acyl-CoA desaturase (N-C18:1CoA -> N-C18:2CoA)
  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 FADS2, LCLAT1, MBOAT7cytosol

• L-tryptophanReach from here →
  1. Carnitine O-Palmitoyltransferase
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. transport of glycine and tryptophan (cytosol to extracellular)

  Catalysed by CPT1A, CPT1C, CPT1B, GLYAT and 3 morecytosol, mitochondrial matrix, extracellular spaceOne of 20 routes

• glutathioneReach from here →
  1. Carnitine O-Palmitoyltransferase
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. gamma-L-glutamyl-L-cysteine + glycine + ATP = glutathione + ADP + phosphate + H(+)

  Catalysed by CPT1A, CPT1C, CPT1B, GLYAT and 3 morecytosol, mitochondrial matrix

• L-threonineReach from here →
  1. Carnitine O-Palmitoyltransferase
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. L-threonine(out) + L-alanine(in) = L-threonine(in) + L-alanine(out)

  Catalysed by CPT1A, CPT1C, CPT1B, SLC7A10cytosol, mitochondrial matrix, inner side of the membrane, outer side of the membraneOne of 4 routes

• L-kynurenineReach from here →
  1. Carnitine O-Palmitoyltransferase
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. L-kynurenine + H2O = anthranilate + L-alanine + H(+)

  Catalysed by CPT1A, CPT1C, CPT1B, KYNUcytosol, mitochondrial matrix

• beta-alanineReach from here →
  1. Carnitine O-Palmitoyltransferase
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. beta-alanine(out) + L-alanine(in) = beta-alanine(in) + L-alanine(out)

  Catalysed by CPT1A, CPT1C, CPT1B, SLC7A10cytosol, mitochondrial matrix, inner side of the membrane, outer side of the membraneOne of 3 routes

• a 1-acyl-sn-glycero-3-phosphateReach from here →
  1. fatty acyl-CoA desaturase (N-C18:1CoA -> N-C18:2CoA)
  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 FADS2, GPAT3, GPAT2, GPAT4 and 1 morecytosol

• leukotriene C4Reach from here →
  1. Carnitine O-Palmitoyltransferase
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. leukotriene C4 hydrolysis

  Catalysed by CPT1A, CPT1C, CPT1B, GLYAT and 2 morecytosol, mitochondrial matrix

• taurocyamineReach from here →
  1. Carnitine O-Palmitoyltransferase
  2. bile acid-CoA:amino acid N-acyltransferase (taurodeoxycholate)
  3. taurine + L-arginine = taurocyamine + L-ornithine

  Catalysed by CPT1A, CPT1C, CPT1B, BAAT and 1 morecytosol

• L-cysteateReach from here →
  1. Carnitine O-Palmitoyltransferase
  2. bile acid-CoA:amino acid N-acyltransferase (taurodeoxycholate)
  3. L-cysteate + H(+) = taurine + CO2

  Catalysed by CPT1A, CPT1C, CPT1B, BAAT and 2 morecytosol

• L-phenylalanineReach from here →
  1. Carnitine O-Palmitoyltransferase
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. transport of glycine and phenylalanine (cytosol to extracellular)

  Catalysed by CPT1A, CPT1C, CPT1B, GLYAT and 3 morecytosol, mitochondrial matrix, extracellular spaceOne of 28 routes

• N(1)-acetylspermineReach from here →
  1. Carnitine O-Palmitoyltransferase
  2. diamine N-acetyltransferase (N1-acetylspermidine)
  3. N(1)-acetylspermine + O2 + H2O = 3-acetamidopropanal + spermidine + H2O2

  Catalysed by CPT1A, CPT1C, CPT1B, SAT1 and 2 morecytosol

• 3-hydroxy-L-kynurenineReach from here →
  1. Carnitine O-Palmitoyltransferase
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. 3-hydroxy-L-kynurenine + H2O = 3-hydroxyanthranilate + L-alanine + H(+)

  Catalysed by CPT1A, CPT1C, CPT1B, KYNUcytosol, mitochondrial matrix

• a 1-acyl-sn-glycero-3-phosphocholineReach from here →
  1. fatty acyl-CoA desaturase (N-C18:1CoA -> N-C18:2CoA)
  2. (9Z,12Z)-octadecadienoyl-CoA + a 1-acyl-sn-glycero-3-phosphocholine = 1-acyl-2-(9Z,12Z)-octadecadienoyl-sn-glycero-3-phosphocholine + CoA
  3. 1-acyl-2-(9Z,12Z)-octadecadienoyl-sn-glycero-3-phosphocholine + H2O = a 1-acyl-sn-glycero-3-phosphocholine + (9Z,12Z)-octadecadienoate + H(+)

  Catalysed by FADS2, LPCAT3, PNPLA8cytosol

• gamma-L-glutamyl-L-cysteineReach from here →
  1. Carnitine O-Palmitoyltransferase
  2. N-acetylglutamate synthase (N-acetyl-L-cysteine)
  3. L-glutamate:L-cysteine gamma-ligase (ADP-forming)

  Catalysed by CPT1A, CPT1C, CPT1B, NAGS and 2 morecytosol, mitochondrial matrixOne of 2 routes

• L-homocysteineReach from here →
  1. Carnitine O-Palmitoyltransferase
  2. N-acetylglutamate synthase (N-acetyl-L-cystathionine)
  3. L-homocysteine + L-serine = L,L-cystathionine + H2O

  Catalysed by CPT1A, CPT1C, CPT1B, NAGS and 1 morecytosol, mitochondrial matrixOne of 2 routes

• S-methyl-L-methionineReach from here →
  1. Carnitine O-Palmitoyltransferase
  2. N-acetylglutamate synthase (N-acetylmethionine)
  3. S-methyl-L-methionine + L-homocysteine = 2 L-methionine + H(+)

  Catalysed by CPT1A, CPT1C, CPT1B, NAGS and 1 morecytosol, mitochondrial matrix

• a 1-acyl-2-(9Z)-octadecenoyl-sn-glycero-3-phosphocholineReach from here →
  1. octadecanoyl-CoA:NADP+ trans-2-oxidoreductase
  2. octadecanoyl-CoA + 2 Fe(II)-[cytochrome b5] + O2 + 2 H(+) = (9Z)-octadecenoyl-CoA + 2 Fe(III)-[cytochrome b5] + 2 H2O
  3. a 1-acyl-sn-glycero-3-phosphocholine + (9Z)-octadecenoyl-CoA = a 1-acyl-2-(9Z)-octadecenoyl-sn-glycero-3-phosphocholine + CoA

  Catalysed by TECRL, TECR, SCD, SCD5 and 1 morecytosol

• 3-oxosphinganineReach from here →
  1. Carnitine O-Palmitoyltransferase
  2. Palmitate:CoA ligase (AMP-forming)
  3. Palmitoyl-CoA:L-serine C-palmitoyltransferase (decarboxylating)

  Catalysed by CPT1A, CPT1C, CPT1B, SLC27A2 and 10 morecytosol

• 1-hexadecanoylglycerone 3-phosphateReach from here →
  1. Carnitine O-Palmitoyltransferase
  2. Palmitate:CoA ligase (AMP-forming)
  3. glyceronephosphate O-acyltransferase (DHAP)

  Catalysed by CPT1A, CPT1C, CPT1B, SLC27A2 and 8 morecytosol, peroxisome

• L-tyrosineReach from here →
  1. Carnitine O-Palmitoyltransferase
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. L-tyrosine + glyoxylate = 3-(4-hydroxyphenyl)pyruvate + glycine

  Catalysed by CPT1A, CPT1C, CPT1B, GLYAT and 3 morecytosol, mitochondrial matrix

• N(1)-acetylspermidineReach from here →
  1. Carnitine O-Palmitoyltransferase
  2. diamine N-acetyltransferase (N1-acetylspermidine)
  3. spermidine + acetyl-CoA = N(1)-acetylspermidine + CoA + H(+)

  Catalysed by CPT1A, CPT1C, CPT1B, SAT1 and 1 morecytosol

• N(omega),N(omega)-dimethyl-L-arginineReach from here →
  1. Carnitine O-Palmitoyltransferase
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. N(omega),N(omega)-dimethyl-L-arginine + glyoxylate = 5-(3,3-dimethylguanidino)-2-oxopentanoate + glycine

  Catalysed by CPT1A, CPT1C, CPT1B, GLYAT and 3 morecytosol, mitochondrial matrixOne of 2 routes

• 3-aminopropanalReach from here →
  1. Carnitine O-Palmitoyltransferase
  2. diamine N-acetyltransferase (N1-acetylspermine)
  3. spermidine:oxygen oxidoreductase (spermidine-forming)

  Catalysed by CPT1A, CPT1C, CPT1B, SAT1 and 2 morecytosol

• trans-4-hydroxy-L-prolineReach from here →
  1. Carnitine O-Palmitoyltransferase
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. trans-4-hydroxy-L-proline(out) + L-alanine(in) + Na(+)(out) = trans-4-hydroxy-L-proline(in) + L-alanine(out) + Na(+)(in)

  Catalysed by CPT1A, CPT1C, CPT1B, SLC1A4cytosol, mitochondrial matrix, inner side of the membrane, outer side of the membraneOne of 2 routes

• N(8)-acetylspermidineReach from here →
  1. Carnitine O-Palmitoyltransferase
  2. diamine N-acetyltransferase (N1-acetylspermidine)
  3. N8-acetylspermidine to spermidine conversion

  Catalysed by CPT1A, CPT1C, CPT1B, SAT1 and 1 morecytosolOne of 3 routes

• N(1),N(12)-diacetylspermineReach from here →
  1. Carnitine O-Palmitoyltransferase
  2. N1,N12-diacetylspermine to N1-acetylspermine conversion
  3. N1,N12-diacetylspermine to N1-acetylspermine conversion

  Catalysed by CPT1A, CPT1C, CPT1BcytosolOne of 2 routes

• (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoateReach from here →
  1. Carnitine O-Palmitoyltransferase
  2. long-chain-fatty-acid-CoA ligase (EPA)
  3. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA hydrolase

  Catalysed by CPT1A, CPT1C, CPT1B, SLC27A2 and 10 morecytosolOne of 2 routes

• S-sulfanyl-L-cysteineReach from here →
  1. Carnitine O-Palmitoyltransferase
  2. N-acetylglutamate synthase (N-acetyl-L-cysteine)
  3. 2 L-cysteine = S-sulfanyl-L-cysteine + L-alanine

  Catalysed by CPT1A, CPT1C, CPT1B, NAGS and 1 morecytosol, mitochondrial matrix