(11Z,14Z)-eicosadienoyl-CoA

Three steps

• beta-alanineReach from here →
  1. (11Z,14Z)-eicosadienoyl-CoA hydrolase
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. beta-alanine(out) + L-alanine(in) = beta-alanine(in) + L-alanine(out)

  Catalysed by BAAT, ACOT6, ACOT1, SLC7A10cytosol, mitochondrial matrix, inner side of the membrane, outer side of the membraneOne of 3 routes

• leukotriene C4Reach from here →
  1. (11Z,14Z)-eicosadienoyl-CoA hydrolase
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. leukotriene C4 hydrolysis

  Catalysed by BAAT, ACOT6, ACOT1, GLYAT and 2 morecytosol, mitochondrial matrix

• taurocyamineReach from here →
  1. (11Z,14Z)-eicosadienoyl-CoA hydrolase
  2. bile acid-CoA:amino acid N-acyltransferase (taurodeoxycholate)
  3. taurine + L-arginine = taurocyamine + L-ornithine

  Catalysed by BAAT, ACOT6, ACOT1, GATMcytosol

• a 1,2-diacyl-sn-glycero-3-phospho-(1D-myo-inositol-3-phosphate)Reach from here →
  1. acyl-CoA pool formation and breakdown
  2. 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
  3. a 1,2-diacyl-sn-glycero-3-phospho-(1D-myo-inositol) + ATP = a 1,2-diacyl-sn-glycero-3-phospho-(1D-myo-inositol-3-phosphate) + ADP + H(+)

  Catalysed by LCLAT1, MBOAT7, PIK3CD, PIK3C2A and 5 morecytosol

• L-cysteateReach from here →
  1. (11Z,14Z)-eicosadienoyl-CoA hydrolase
  2. bile acid-CoA:amino acid N-acyltransferase (taurodeoxycholate)
  3. L-cysteate + H(+) = taurine + CO2

  Catalysed by BAAT, ACOT6, ACOT1, GADL1 and 1 morecytosol

• L-phenylalanineReach from here →
  1. (11Z,14Z)-eicosadienoyl-CoA hydrolase
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. transport of glycine and phenylalanine (cytosol to extracellular)

  Catalysed by BAAT, ACOT6, ACOT1, GLYAT and 3 morecytosol, mitochondrial matrix, extracellular spaceOne of 28 routes

• N(1)-acetylspermineReach from here →
  1. (11Z,14Z)-eicosadienoyl-CoA hydrolase
  2. diamine N-acetyltransferase (N1-acetylspermidine)
  3. N(1)-acetylspermine + O2 + H2O = 3-acetamidopropanal + spermidine + H2O2

  Catalysed by BAAT, ACOT6, ACOT1, SAT1 and 2 morecytosol

• 3-hydroxy-L-kynurenineReach from here →
  1. (11Z,14Z)-eicosadienoyl-CoA hydrolase
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. 3-hydroxy-L-kynurenine + H2O = 3-hydroxyanthranilate + L-alanine + H(+)

  Catalysed by BAAT, ACOT6, ACOT1, KYNUcytosol, mitochondrial matrix

• a 1-acyl-sn-glycero-3-phosphocholineReach from here →
  1. acyl-CoA pool formation and breakdown
  2. a 2-acyl-sn-glycero-3-phosphocholine + an acyl-CoA = a 1,2-diacyl-sn-glycero-3-phosphocholine + CoA
  3. a 1,2-diacyl-sn-glycero-3-phosphocholine + H2O = a 1-acyl-sn-glycero-3-phosphocholine + a fatty acid + H(+)

  Catalysed by LPGAT1, PLA2G10, PLA2G6, PLA2G1B and 27 morecytosolOne of 14 routes

• gamma-L-glutamyl-L-cysteineReach from here →
  1. (11Z,14Z)-eicosadienoyl-CoA hydrolase
  2. N-acetylglutamate synthase (N-acetyl-L-cysteine)
  3. L-glutamate:L-cysteine gamma-ligase (ADP-forming)

  Catalysed by BAAT, ACOT6, ACOT1, NAGS and 2 morecytosol, mitochondrial matrixOne of 2 routes

• a 1,2-diacyl-sn-glycero-3-phospho-(1D-myo-inositol 4-phosphate)Reach from here →
  1. acyl-CoA pool formation and breakdown
  2. a 2-acyl-sn-glycero-3-phosphocholine + an acyl-CoA = a 1,2-diacyl-sn-glycero-3-phosphocholine + CoA
  3. a 1,2-diacyl-sn-glycero-3-phospho-(1D-myo-inositol 4-phosphate)(out) + a 1,2-diacyl-sn-glycero-3-phosphocholine(in) = a 1,2-diacyl-sn-glycero-3-phospho-(1D-myo-inositol 4-phosphate)(in) + a 1,2-diacyl-sn-glycero-3-phosphocholine(out)

  Catalysed by LPGAT1, OSBPL3cytosol, inner side of the membrane, outer side of the membraneOne of 5 routes

• phosphoethanolamineReach from here →
  1. acyl-CoA pool formation and breakdown
  2. a 1-acyl-sn-glycero-3-phosphoethanolamine + an acyl-CoA = a 1,2-diacyl-sn-glycero-3-phosphoethanolamine + CoA
  3. a 1,2-diacyl-sn-glycero-3-phosphoethanolamine + H2O = phosphoethanolamine + a 1,2-diacyl-sn-glycerol + H(+)

  Catalysed by LPCAT4, LPCAT3, MBOAT1, MBOAT2 and 1 morecytosol

• L-homocysteineReach from here →
  1. (11Z,14Z)-eicosadienoyl-CoA hydrolase
  2. N-acetylglutamate synthase (N-acetyl-L-cystathionine)
  3. L-homocysteine + L-serine = L,L-cystathionine + H2O

  Catalysed by BAAT, ACOT6, ACOT1, NAGS and 1 morecytosol, mitochondrial matrixOne of 2 routes

• S-methyl-L-methionineReach from here →
  1. (11Z,14Z)-eicosadienoyl-CoA hydrolase
  2. N-acetylglutamate synthase (N-acetylmethionine)
  3. S-methyl-L-methionine + L-homocysteine = 2 L-methionine + H(+)

  Catalysed by BAAT, ACOT6, ACOT1, NAGS and 1 morecytosol, mitochondrial matrix

• 3-oxosphinganineReach from here →
  1. (11Z,14Z)-eicosadienoyl-CoA hydrolase
  2. Palmitate:CoA ligase (AMP-forming)
  3. Palmitoyl-CoA:L-serine C-palmitoyltransferase (decarboxylating)

  Catalysed by BAAT, ACOT6, ACOT1, SLC27A2 and 10 morecytosol

• 1-hexadecanoylglycerone 3-phosphateReach from here →
  1. (11Z,14Z)-eicosadienoyl-CoA hydrolase
  2. Palmitate:CoA ligase (AMP-forming)
  3. glyceronephosphate O-acyltransferase (DHAP)

  Catalysed by BAAT, ACOT6, ACOT1, SLC27A2 and 8 morecytosol, peroxisome

• L-tyrosineReach from here →
  1. (11Z,14Z)-eicosadienoyl-CoA hydrolase
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. L-tyrosine + glyoxylate = 3-(4-hydroxyphenyl)pyruvate + glycine

  Catalysed by BAAT, ACOT6, ACOT1, GLYAT and 3 morecytosol, mitochondrial matrix

• N(1)-acetylspermidineReach from here →
  1. (11Z,14Z)-eicosadienoyl-CoA hydrolase
  2. diamine N-acetyltransferase (N1-acetylspermidine)
  3. spermidine + acetyl-CoA = N(1)-acetylspermidine + CoA + H(+)

  Catalysed by BAAT, ACOT6, ACOT1, SAT1 and 1 morecytosol

• N(omega),N(omega)-dimethyl-L-arginineReach from here →
  1. (11Z,14Z)-eicosadienoyl-CoA hydrolase
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. N(omega),N(omega)-dimethyl-L-arginine + glyoxylate = 5-(3,3-dimethylguanidino)-2-oxopentanoate + glycine

  Catalysed by BAAT, ACOT6, ACOT1, GLYAT and 3 morecytosol, mitochondrial matrixOne of 2 routes

• a CDP-1,2-diacyl-sn-glycerolReach from here →
  1. acyl-CoA pool formation and breakdown
  2. a 1-acyl-sn-glycero-3-phosphate + an acyl-CoA = a 1,2-diacyl-sn-glycero-3-phosphate + CoA
  3. a 1,2-diacyl-sn-glycero-3-phosphate + CTP + H(+) = a CDP-1,2-diacyl-sn-glycerol + diphosphate

  Catalysed by AGPAT2, GPAT3, GPAT2, LCLAT1 and 12 morecytosolOne of 3 routes

• 3-aminopropanalReach from here →
  1. (11Z,14Z)-eicosadienoyl-CoA hydrolase
  2. diamine N-acetyltransferase (N1-acetylspermine)
  3. spermidine:oxygen oxidoreductase (spermidine-forming)

  Catalysed by BAAT, ACOT6, ACOT1, SAT1 and 2 morecytosol

• trans-4-hydroxy-L-prolineReach from here →
  1. (11Z,14Z)-eicosadienoyl-CoA hydrolase
  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 BAAT, ACOT6, ACOT1, SLC1A4cytosol, mitochondrial matrix, inner side of the membrane, outer side of the membraneOne of 2 routes

• 1D-myo-inositol 1-phosphateReach from here →
  1. acyl-CoA pool formation and breakdown
  2. 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
  3. a 1,2-diacyl-sn-glycero-3-phospho-(1D-myo-inositol) + H2O = 1D-myo-inositol 1-phosphate + a 1,2-diacyl-sn-glycerol + H(+)

  Catalysed by LCLAT1, MBOAT7, PLCG1, PLCD1 and 6 morecytosol

• N(8)-acetylspermidineReach from here →
  1. (11Z,14Z)-eicosadienoyl-CoA hydrolase
  2. diamine N-acetyltransferase (N1-acetylspermidine)
  3. N8-acetylspermidine to spermidine conversion

  Catalysed by BAAT, ACOT6, ACOT1, SAT1 and 1 morecytosolOne of 3 routes

• N(1),N(12)-diacetylspermineReach from here →
  1. (11Z,14Z)-eicosadienoyl-CoA hydrolase
  2. N1,N12-diacetylspermine to N1-acetylspermine conversion
  3. N1,N12-diacetylspermine to N1-acetylspermine conversion

  Catalysed by BAAT, ACOT6, ACOT1cytosolOne of 2 routes

• (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoateReach from here →
  1. (11Z,14Z)-eicosadienoyl-CoA hydrolase
  2. (10Z)-heptadecenoic acid formation
  3. (10Z)-heptadecenoic acid formation

  Catalysed by BAAT, ACOT6, ACOT1cytosol, extracellular spaceOne of 14 routes

• S-sulfanyl-L-cysteineReach from here →
  1. (11Z,14Z)-eicosadienoyl-CoA hydrolase
  2. N-acetylglutamate synthase (N-acetyl-L-cysteine)
  3. 2 L-cysteine = S-sulfanyl-L-cysteine + L-alanine

  Catalysed by BAAT, ACOT6, ACOT1, NAGS and 1 morecytosol, mitochondrial matrix

• (3S)-citramalyl-CoAReach from here →
  1. (11Z,14Z)-eicosadienoyl-CoA hydrolase
  2. Itaconate:CoA ligase (GDP-forming)
  3. (3S)-citramalyl-CoA = itaconyl-CoA + H2O

  Catalysed by BAAT, ACOT6, ACOT1, SUCLG1 and 3 morecytosol, mitochondrial matrix

• phosphoenolpyruvateReach from here →
  1. (11Z,14Z)-eicosadienoyl-CoA hydrolase
  2. ATP citrate lyase (citrate)
  3. oxaloacetate + GTP = phosphoenolpyruvate + GDP + CO2

  Catalysed by BAAT, ACOT6, ACOT1, ACLY and 2 morecytosol

• L-methionine (S)-S-oxideReach from here →
  1. (11Z,14Z)-eicosadienoyl-CoA hydrolase
  2. N-acetylglutamate synthase (N-acetylmethionine)
  3. [thioredoxin]-disulfide + L-methionine + H2O = L-methionine (S)-S-oxide + [thioredoxin]-dithiol

  Catalysed by BAAT, ACOT6, ACOT1, NAGS and 1 morecytosol, mitochondrial matrix

• L-methionine (R)-S-oxideReach from here →
  1. (11Z,14Z)-eicosadienoyl-CoA hydrolase
  2. N-acetylglutamate synthase (N-acetylmethionine)
  3. [thioredoxin]-disulfide + L-methionine + H2O = L-methionine (R)-S-oxide + [thioredoxin]-dithiol

  Catalysed by BAAT, ACOT6, ACOT1, NAGS and 3 morecytosol, mitochondrial matrix

• N-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-glycineReach from here →
  1. (11Z,14Z)-eicosadienoyl-CoA hydrolase
  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 BAAT, ACOT6, ACOT1, GLYAT and 2 morecytosol, mitochondrial matrixOne of 3 routes

• N-[(R)-4-phosphopantothenoyl]-L-cysteineReach from here →
  1. (11Z,14Z)-eicosadienoyl-CoA hydrolase
  2. N-acetylglutamate synthase (N-acetyl-L-cysteine)
  3. (R)-4'-phosphopantothenate:L-cysteine ligase

  Catalysed by BAAT, ACOT6, ACOT1, NAGS and 1 morecytosol, mitochondrial matrixOne of 4 routes

• 1-acyl-2-(9Z,12Z)-octadecadienoyl-sn-glycero-3-phosphocholineReach from here →
  1. (11Z,14Z)-eicosadienoyl-CoA hydrolase
  2. long-chain-fatty-acid-CoA ligase ((6Z,9Z)-octadecadienoic acid)
  3. (9Z,12Z)-octadecadienoyl-CoA + a 1-acyl-sn-glycero-3-phosphocholine = 1-acyl-2-(9Z,12Z)-octadecadienoyl-sn-glycero-3-phosphocholine + CoA

  Catalysed by BAAT, ACOT6, ACOT1, SLC27A2 and 8 morecytosol

• L-prolineReach from here →
  1. (11Z,14Z)-eicosadienoyl-CoA hydrolase
  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 BAAT, ACOT6, ACOT1, SLC1A4cytosol, mitochondrial matrix, inner side of the membrane, outer side of the membraneOne of 2 routes

• sphing-4-enine 1-phosphateReach from here →
  1. (11Z,14Z)-eicosadienoyl-CoA hydrolase
  2. acyl-CoA:sphingosine N-acyltransferase
  3. sphing-4-enine + ATP = sphing-4-enine 1-phosphate + ADP + H(+)

  Catalysed by BAAT, ACOT6, ACOT1, ASAH1 and 5 morecytosol, Golgi apparatus

• N-benzoylglycineReach from here →
  1. (11Z,14Z)-eicosadienoyl-CoA hydrolase
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. Hippurate (Benzoylglycinate) Formation

  Catalysed by BAAT, ACOT6, ACOT1, GLYAT and 2 morecytosol, mitochondrial matrixOne of 2 routes

• 3-sulfino-L-alanineReach from here →
  1. (11Z,14Z)-eicosadienoyl-CoA hydrolase
  2. N-acetylglutamate synthase (N-acetyl-L-cysteine)
  3. L-Cysteine:oxygen oxidoreductase

  Catalysed by BAAT, ACOT6, ACOT1, NAGS and 1 morecytosol, mitochondrial matrixOne of 2 routes

• (2E)-tetradecenoyl-CoAReach from here →
  1. (11Z,14Z)-eicosadienoyl-CoA hydrolase
  2. long-chain-fatty-acid-CoA ligase (myristic acid)
  3. trans-tetradec-2-enoyl-CoA reductase

  Catalysed by BAAT, ACOT6, ACOT1, SLC27A2 and 8 morecytosol, mitochondrial matrixOne of 5 routes

• (2E)-decenoyl-CoAReach from here →
  1. (11Z,14Z)-eicosadienoyl-CoA hydrolase
  2. medium-chain acyl-CoA ligase (decanoic acid)
  3. trans-dec-2-enoyl-CoA reductase

  Catalysed by BAAT, ACOT6, ACOT1, ACSM4 and 6 morecytosol, mitochondrial matrixOne of 8 routes

• L-cysteinylglycineReach from here →
  1. (11Z,14Z)-eicosadienoyl-CoA hydrolase
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. gamma-glutamyltransferase (alanine)

  Catalysed by BAAT, ACOT6, ACOT1, GGTLC3 and 5 morecytosol, mitochondrial matrixOne of 2 routes

• (2E)-hexenoyl-CoAReach from here →
  1. (11Z,14Z)-eicosadienoyl-CoA hydrolase
  2. medium-chain acyl-CoA ligase (hexanoic acid)
  3. trans-hex-2-enoyl-CoA reductase

  Catalysed by BAAT, ACOT6, ACOT1, ACSM4 and 6 morecytosol, mitochondrial matrixOne of 3 routes

• (2E)-octenoyl-CoAReach from here →
  1. (11Z,14Z)-eicosadienoyl-CoA hydrolase
  2. Octanoyl-CoA:L-carnitine O-octanoyltransferase
  3. trans-oct-2-enoyl-CoA reductase

  Catalysed by BAAT, ACOT6, ACOT1, CROT and 1 morecytosol, mitochondrial matrixOne of 5 routes

• an N-acyl-1,2-diacyl-sn-glycero-3-phosphoethanolamineReach from here →
  1. acyl-CoA pool formation and breakdown
  2. a 2-acyl-sn-glycero-3-phosphocholine + an acyl-CoA = a 1,2-diacyl-sn-glycero-3-phosphocholine + CoA
  3. a 1,2-diacyl-sn-glycero-3-phosphoethanolamine + a 1,2-diacyl-sn-glycero-3-phosphocholine = an N-acyl-1,2-diacyl-sn-glycero-3-phosphoethanolamine + a 2-acyl-sn-glycero-3-phosphocholine + H(+)

  Catalysed by LPGAT1, PLA2G4E, PLAAT5, PLAAT2cytosolOne of 4 routes

• 3-oxotetradecanoyl-CoAReach from here →
  1. (11Z,14Z)-eicosadienoyl-CoA hydrolase
  2. long-chain-fatty-acid-CoA ligase (lauric acid)
  3. dodecanoyl-CoA + malonyl-CoA + H(+) = 3-oxotetradecanoyl-CoA + CO2 + CoA

  Catalysed by BAAT, ACOT6, ACOT1, SLC27A2 and 8 morecytosol

• a 1-acyl-sn-glycero-3-phospho-L-serineReach from here →
  1. acyl-CoA pool formation and breakdown
  2. a 1-acyl-sn-glycero-3-phospho-L-serine + an acyl-CoA = a 1,2-diacyl-sn-glycero-3-phospho-L-serine + CoA
  3. a 1,2-diacyl-sn-glycero-3-phospho-L-serine + N-(acetyl)-sphing-4-enine = 1-O-acyl-N-(acetyl)-sphing-4-enine + a 1-acyl-sn-glycero-3-phospho-L-serine

  Catalysed by LPCAT4, LPCAT3, MBOAT1, PLA2G15cytosol

• a 1-acyl-sn-glycero-3-phosphoethanolamineReach from here →
  1. acyl-CoA pool formation and breakdown
  2. a 1-acyl-sn-glycero-3-phosphoethanolamine + an acyl-CoA = a 1,2-diacyl-sn-glycero-3-phosphoethanolamine + CoA
  3. N-(acetyl)-sphing-4-enine + a 1,2-diacyl-sn-glycero-3-phosphoethanolamine = 1-O-acyl-N-(acetyl)-sphing-4-enine + a 1-acyl-sn-glycero-3-phosphoethanolamine

  Catalysed by LPCAT4, LPCAT3, MBOAT1, MBOAT2 and 1 morecytosolOne of 2 routes

• 1-O-hexadecyl-sn-glycero-3-phosphocholineReach from here →
  1. (11Z,14Z)-eicosadienoyl-CoA hydrolase
  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 BAAT, ACOT6, ACOT1, ASAH1 and 4 morecytosol, Golgi apparatus

• a 1,2-diacyl-sn-glycero-3-phospho-N-methylethanolamineReach from here →
  1. acyl-CoA pool formation and breakdown
  2. a 1-acyl-sn-glycero-3-phosphoethanolamine + an acyl-CoA = a 1,2-diacyl-sn-glycero-3-phosphoethanolamine + CoA
  3. a 1,2-diacyl-sn-glycero-3-phosphoethanolamine + S-adenosyl-L-methionine = a 1,2-diacyl-sn-glycero-3-phospho-N-methylethanolamine + S-adenosyl-L-homocysteine + H(+)

  Catalysed by LPCAT4, LPCAT3, MBOAT1, MBOAT2 and 1 morecytosol

• a 1-acyl-sn-glycerolReach from here →
  1. acyl-CoA pool formation and breakdown
  2. sn-glycerol 3-phosphate + an acyl-CoA = a 1-acyl-sn-glycero-3-phosphate + CoA
  3. a 1-acyl-sn-glycero-3-phosphate + H2O = a 1-acyl-sn-glycerol + phosphate

  Catalysed by GPAT3, GPAT2, GPAT4, GPAM and 2 morecytosolOne of 2 routes