(11Z)-octadecenoyl-CoA

Three steps

• L-tryptophanReach from here →
  1. Transport of 11-Octadecenoyl Carnitine into the Mitochondrial Matrix
  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. Transport of 11-Octadecenoyl Carnitine into the Mitochondrial Matrix
  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. Transport of 11-Octadecenoyl Carnitine into the Mitochondrial Matrix
  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. Transport of 11-Octadecenoyl Carnitine into the Mitochondrial Matrix
  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. Transport of 11-Octadecenoyl Carnitine into the Mitochondrial Matrix
  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. Transport of 11-Octadecenoyl Carnitine into the Mitochondrial Matrix
  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. Transport of 11-Octadecenoyl Carnitine into the Mitochondrial Matrix
  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. Transport of 11-Octadecenoyl Carnitine into the Mitochondrial Matrix
  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. Transport of 11-Octadecenoyl Carnitine into the Mitochondrial Matrix
  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. Transport of 11-Octadecenoyl Carnitine into the Mitochondrial Matrix
  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. Transport of 11-Octadecenoyl Carnitine into the Mitochondrial Matrix
  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. Transport of 11-Octadecenoyl Carnitine into the Mitochondrial Matrix
  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. Transport of 11-Octadecenoyl Carnitine into the Mitochondrial Matrix
  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. Transport of 11-Octadecenoyl Carnitine into the Mitochondrial Matrix
  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

• 3-oxosphinganineReach from here →
  1. Fatty Acid Beta Oxidation (C18:1->C16:1), Mitochondrial
  2. hexadecanoyl-CoA + 2 Fe(II)-[cytochrome b5] + O2 + 2 H(+) = (9Z)-hexadecenoyl-CoA + 2 Fe(III)-[cytochrome b5] + 2 H2O
  3. L-serine + hexadecanoyl-CoA + H(+) = 3-oxosphinganine + CO2 + CoA

  Catalysed by HADHA, ACADVL, HADHB, SCD and 4 moremitochondrial matrixOne of 2 routes

• 1-hexadecanoylglycerone 3-phosphateReach from here →
  1. Fatty Acid Beta Oxidation (C18:1->C16:1), Mitochondrial
  2. hexadecanoyl-CoA + 2 Fe(II)-[cytochrome b5] + O2 + 2 H(+) = (9Z)-hexadecenoyl-CoA + 2 Fe(III)-[cytochrome b5] + 2 H2O
  3. dihydroxyacetone phosphate + hexadecanoyl-CoA = 1-hexadecanoylglycerone 3-phosphate + CoA

  Catalysed by HADHA, ACADVL, HADHB, SCD and 2 moremitochondrial matrixOne of 2 routes

• L-tyrosineReach from here →
  1. Transport of 11-Octadecenoyl Carnitine into the Mitochondrial Matrix
  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. Transport of 11-Octadecenoyl Carnitine into the Mitochondrial Matrix
  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. Transport of 11-Octadecenoyl Carnitine into the Mitochondrial Matrix
  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. Transport of 11-Octadecenoyl Carnitine into the Mitochondrial Matrix
  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. Transport of 11-Octadecenoyl Carnitine into the Mitochondrial Matrix
  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. Transport of 11-Octadecenoyl Carnitine into the Mitochondrial Matrix
  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. Transport of 11-Octadecenoyl Carnitine into the Mitochondrial Matrix
  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. Transport of 11-Octadecenoyl Carnitine into the Mitochondrial Matrix
  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. Transport of 11-Octadecenoyl Carnitine into the Mitochondrial Matrix
  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

• a 1,2-diacyl-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. a 1-acyl-sn-glycero-3-phosphate + an acyl-CoA = a 1,2-diacyl-sn-glycero-3-phosphate + CoA

  Catalysed by FADS2, AGPAT2, GPAT3, GPAT2 and 10 morecytosol

• (3S)-citramalyl-CoAReach from here →
  1. Transport of 11-Octadecenoyl Carnitine into the Mitochondrial Matrix
  2. Itaconate:CoA ligase (GDP-forming)
  3. (3S)-citramalyl-CoA = itaconyl-CoA + H2O

  Catalysed by CPT1A, CPT1C, CPT1B, SUCLG1 and 3 morecytosol, mitochondrial matrix

• phosphoenolpyruvateReach from here →
  1. Transport of 11-Octadecenoyl Carnitine into the Mitochondrial Matrix
  2. ATP citrate lyase (citrate)
  3. oxaloacetate + GTP = phosphoenolpyruvate + GDP + CO2

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

• L-methionine (S)-S-oxideReach from here →
  1. Transport of 11-Octadecenoyl Carnitine into the Mitochondrial Matrix
  2. N-acetylglutamate synthase (N-acetylmethionine)
  3. [thioredoxin]-disulfide + L-methionine + H2O = L-methionine (S)-S-oxide + [thioredoxin]-dithiol

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

• L-methionine (R)-S-oxideReach from here →
  1. Transport of 11-Octadecenoyl Carnitine into the Mitochondrial Matrix
  2. N-acetylglutamate synthase (N-acetylmethionine)
  3. [thioredoxin]-disulfide + L-methionine + H2O = L-methionine (R)-S-oxide + [thioredoxin]-dithiol

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

• N-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-glycineReach from here →
  1. Transport of 11-Octadecenoyl Carnitine into the Mitochondrial Matrix
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA + glycine = N-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-glycine + CoA + H(+)

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

• N-[(R)-4-phosphopantothenoyl]-L-cysteineReach from here →
  1. Transport of 11-Octadecenoyl Carnitine into the Mitochondrial Matrix
  2. N-acetylglutamate synthase (N-acetyl-L-cysteine)
  3. (R)-4'-phosphopantothenate:L-cysteine ligase

  Catalysed by CPT1A, CPT1C, CPT1B, NAGS and 1 morecytosol, mitochondrial matrixOne of 4 routes

• monodehydro-L-ascorbate radicalReach from here →
  1. Beta Oxidation Fatty Acid
  2. octanoyl-CoA + glycine = N-octanoylglycine + CoA + H(+)
  3. N-octanoylglycine + 2 L-ascorbate + O2 = N-octanoyl-(2S)-hydroxyglycine + 2 monodehydro-L-ascorbate radical + H2O

  Catalysed by ACADM, ACADS, GLYATL2, PAMmitochondrial matrix

• L-prolineReach from here →
  1. Transport of 11-Octadecenoyl Carnitine into the Mitochondrial Matrix
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. L-proline(out) + L-alanine(in) + Na(+)(out) = 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

• sphing-4-enine 1-phosphateReach from here →
  1. Transport of 11-Octadecenoyl Carnitine into the Mitochondrial Matrix
  2. acyl-CoA:sphingosine N-acyltransferase
  3. sphing-4-enine + ATP = sphing-4-enine 1-phosphate + ADP + H(+)

  Catalysed by CPT1A, CPT1C, CPT1B, ASAH1 and 5 morecytosol, Golgi apparatus

• N-benzoylglycineReach from here →
  1. Transport of 11-Octadecenoyl Carnitine into the Mitochondrial Matrix
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. Hippurate (Benzoylglycinate) Formation

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

• (9S)-hydroperoxy-(10E,12Z)-octadecadienoateReach from here →
  1. fatty acyl-CoA desaturase (N-C18:1CoA -> N-C18:2CoA)
  2. Linoleoyl-CoA hydrolase
  3. linoleate:oxygen 9-oxidoreductase

  Catalysed by FADS2, ACOT7, BAAT, THEM4 and 2 morecytosol

• 3-sulfino-L-alanineReach from here →
  1. Transport of 11-Octadecenoyl Carnitine into the Mitochondrial Matrix
  2. N-acetylglutamate synthase (N-acetyl-L-cysteine)
  3. L-Cysteine:oxygen oxidoreductase

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

• (2E)-tetradecenoyl-CoAReach from here →
  1. Transport of 11-Octadecenoyl Carnitine into the Mitochondrial Matrix
  2. long-chain-fatty-acid-CoA ligase (myristic acid)
  3. trans-tetradec-2-enoyl-CoA reductase

  Catalysed by CPT1A, CPT1C, CPT1B, SLC27A2 and 8 morecytosol, mitochondrial matrixOne of 5 routes

• (2E)-decenoyl-CoAReach from here →
  1. Beta Oxidation Fatty Acid
  2. fatty acyl-CoA synthase (N-C10:0CoA)
  3. trans-dec-2-enoyl-CoA reductase

  Catalysed by ACADM, ACADS, MECRmitochondrial matrix, cytosolOne of 8 routes

• L-cysteinylglycineReach from here →
  1. Transport of 11-Octadecenoyl Carnitine into the Mitochondrial Matrix
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. gamma-glutamyltransferase (alanine)

  Catalysed by CPT1A, CPT1C, CPT1B, GGTLC3 and 5 morecytosol, mitochondrial matrixOne of 2 routes

• (2E)-hexenoyl-CoAReach from here →
  1. Beta Oxidation Fatty Acid
  2. Fatty Acid Beta Oxidation (C8->C6), Peroxisomal
  3. trans-hex-2-enoyl-CoA reductase

  Catalysed by ACADM, ACADS, ACAA1, HSD17B4 and 3 moremitochondrial matrix, peroxisomeOne of 3 routes

• a cardiolipinReach from here →
  1. fatty acyl-CoA desaturase (N-C18:1CoA -> N-C18:2CoA)
  2. acyl-CoA pool formation and breakdown
  3. 1'-[1,2-diacyl-sn-glycero-3-phospho],3'-[1-acyl-sn-glycero-3-phospho]-glycerol + an acyl-CoA = a cardiolipin + CoA

  Catalysed by FADS2, HADHAcytosol

• 3-oxotetradecanoyl-CoAReach from here →
  1. Transport of 11-Octadecenoyl Carnitine into the Mitochondrial Matrix
  2. long-chain-fatty-acid-CoA ligase (lauric acid)
  3. dodecanoyl-CoA + malonyl-CoA + H(+) = 3-oxotetradecanoyl-CoA + CO2 + CoA

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

• an all-trans-retinyl esterReach from here →
  1. fatty acyl-CoA desaturase (N-C18:1CoA -> N-C18:2CoA)
  2. acyl-CoA pool formation and breakdown
  3. all-trans-retinol + an acyl-CoA = an all-trans-retinyl ester + CoA

  Catalysed by FADS2, DGAT1, PNPLA4, AWAT2 and 1 morecytosolOne of 4 routes

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

  Catalysed by FADS2, LPCAT3, PNPLA8cytosol

• 1-O-hexadecyl-sn-glycero-3-phosphocholineReach from here →
  1. Transport of 11-Octadecenoyl Carnitine into the Mitochondrial Matrix
  2. acyl-CoA:sphingosine N-acyltransferase
  3. 1-O-hexadecyl-2-acetyl-sn-glycero-3-phosphocholine + sphing-4-enine = 1-O-hexadecyl-sn-glycero-3-phosphocholine + N-(acetyl)-sphing-4-enine + H(+)

  Catalysed by CPT1A, CPT1C, CPT1B, ASAH1 and 4 morecytosol, Golgi apparatus

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

  Catalysed by FADS2, LPCAT4, LPCAT3, MBOAT1 and 1 morecytosol