elaidic acid

Three steps

• leukotriene A4Reach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + O2 = leukotriene A4 + H2O

  Catalysed by ALOX5cytosol, extracellular space

• (13S)-hydroperoxy-(9Z,11E)-octadecadienoateReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. Linoleate:oxygen 13-oxidoreductase

  Catalysed by ALOX15B, ALOX15cytosol, extracellular space

• propane-1,3-diamineReach from here →
  1. (9E)-octadecenoyl-CoA hydrolase
  2. diamine N-acetyltransferase (N1-acetylspermidine)
  3. [eIF5A protein]-L-lysine + spermidine = [eIF5A protein]-deoxyhypusine + propane-1,3-diamine

  Catalysed by ACOT7, BAAT, THEM4, ACOT1 and 4 morecytosol

• 1-hexadecanoyl-sn-glycero-3-phosphateReach from here →
  1. (9E)-octadecenoyl-CoA hydrolase
  2. Palmitate:CoA ligase (AMP-forming)
  3. glycerol-3-phosphate 1-O-acyltransferase (palmitoyl-CoA)

  Catalysed by ACOT7, BAAT, THEM4, ACOT1 and 13 morecytosolOne of 2 routes

• a long-chain fatty acidReach from here →
  1. acyl-CoA pool formation and breakdown
  2. dihydroxyacetone phosphate + an acyl-CoA = a 1-acylglycerone 3-phosphate + CoA
  3. a long chain fatty alcohol + a 1-acylglycerone 3-phosphate = a 1-O-alkylglycerone 3-phosphate + a long-chain fatty acid + H(+)

  Catalysed by GNPAT, AGPScytosol

• (R)-2-hydroxyoctadecanoateReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. octadecanoate + 2 Fe(II)-[cytochrome b5] + O2 + 2 H(+) = (R)-2-hydroxyoctadecanoate + 2 Fe(III)-[cytochrome b5] + H2O

  Catalysed by FA2Hcytosol, extracellular space

• O-acetyl-(R)-carnitineReach from here →
  1. (9E)-octadecenoyl-CoA hydrolase
  2. Carnitine O-Palmitoyltransferase
  3. Acetyl-CoA:carnitine O-acetyltransferase

  Catalysed by ACOT7, BAAT, THEM4, ACOT1 and 4 morecytosolOne of 9 routes

• ethanolamineReach from here →
  1. acyl-CoA pool formation and breakdown
  2. Acyl-CoA:1-acyl-sn-glycero-3-phosphoethanolamine O-acyltransferase
  3. L-1-phosphatidylethanolamine:L-serine phosphatidyltransferase

  Catalysed by LPCAT4, LPCAT3, LPCAT2, LPCAT1 and 2 morecytosolOne of 4 routes

• 2-oxo-3-sulfanylpropanoateReach from here →
  1. (9E)-octadecenoyl-CoA hydrolase
  2. N-acetylglutamate synthase (N-acetyl-L-cysteine)
  3. L-Cysteine:2-oxoglutarate aminotransferase

  Catalysed by ACOT7, BAAT, THEM4, ACOT1 and 4 morecytosol, mitochondrial matrixOne of 3 routes

• guanidinoacetateReach from here →
  1. (9E)-octadecenoyl-CoA hydrolase
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. L-Arginine:glycine amidinotransferase

  Catalysed by ACOT7, BAAT, THEM4, ACOT1 and 5 morecytosol, mitochondrial matrixOne of 2 routes

• D-threonineReach from here →
  1. (9E)-octadecenoyl-CoA hydrolase
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. D-threonine(out) + L-alanine(in) = D-threonine(in) + L-alanine(out)

  Catalysed by ACOT7, BAAT, THEM4, ACOT1 and 2 morecytosol, mitochondrial matrix, inner side of the membrane, outer side of the membraneOne of 2 routes

• a 1,2-diacyl-sn-glycero-3-phospho-(1D-myo-inositol-5-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-5-phosphate) + ADP + H(+)

  Catalysed by LCLAT1, MBOAT7, PIKFYVEcytosol

• sphinganineReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. N-acylsphingosine amidohydrolase
  3. an N-acylsphinganine + H2O = sphinganine + a fatty acid

  Catalysed by ASAH1, ACER2, ACER1, ASAH2 and 1 morecytosol

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

  Catalysed by LPGAT1cytosolOne of 12 routes

• CDP-ethanolamineReach from here →
  1. acyl-CoA pool formation and breakdown
  2. Acyl-CoA:1-alkenylglycerophosphoethanolamine O-acyltransferase
  3. ethanolaminephosphotransferase (1-alkenyl-2-acylglycerol)

  Catalysed by LPCAT4, LPCAT3, LPCAT2, LPCAT1 and 2 morecytosol

• L-tryptophanReach from here →
  1. (9E)-octadecenoyl-CoA hydrolase
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. transport of glycine and tryptophan (cytosol to extracellular)

  Catalysed by ACOT7, BAAT, THEM4, ACOT1 and 5 morecytosol, mitochondrial matrix, extracellular spaceOne of 20 routes

• glutathioneReach from here →
  1. (9E)-octadecenoyl-CoA hydrolase
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. gamma-L-glutamyl-L-cysteine + glycine + ATP = glutathione + ADP + phosphate + H(+)

  Catalysed by ACOT7, BAAT, THEM4, ACOT1 and 5 morecytosol, mitochondrial matrix

• L-threonineReach from here →
  1. (9E)-octadecenoyl-CoA hydrolase
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. L-threonine(out) + L-alanine(in) = L-threonine(in) + L-alanine(out)

  Catalysed by ACOT7, BAAT, THEM4, ACOT1 and 2 morecytosol, mitochondrial matrix, inner side of the membrane, outer side of the membraneOne of 4 routes

• L-kynurenineReach from here →
  1. (9E)-octadecenoyl-CoA hydrolase
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. L-kynurenine + H2O = anthranilate + L-alanine + H(+)

  Catalysed by ACOT7, BAAT, THEM4, ACOT1 and 2 morecytosol, mitochondrial matrix

• beta-alanineReach from here →
  1. (9E)-octadecenoyl-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 ACOT7, BAAT, THEM4, ACOT1 and 2 morecytosol, mitochondrial matrix, inner side of the membrane, outer side of the membraneOne of 3 routes

• leukotriene C4Reach from here →
  1. (9E)-octadecenoyl-CoA hydrolase
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. leukotriene C4 hydrolysis

  Catalysed by ACOT7, BAAT, THEM4, ACOT1 and 4 morecytosol, mitochondrial matrix

• taurocyamineReach from here →
  1. (9E)-octadecenoyl-CoA hydrolase
  2. bile acid-CoA:amino acid N-acyltransferase (taurodeoxycholate)
  3. taurine + L-arginine = taurocyamine + L-ornithine

  Catalysed by ACOT7, BAAT, THEM4, ACOT1 and 2 morecytosol

• 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. (9E)-octadecenoyl-CoA hydrolase
  2. bile acid-CoA:amino acid N-acyltransferase (taurodeoxycholate)
  3. L-cysteate + H(+) = taurine + CO2

  Catalysed by ACOT7, BAAT, THEM4, ACOT1 and 3 morecytosol

• L-phenylalanineReach from here →
  1. (9E)-octadecenoyl-CoA hydrolase
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. transport of glycine and phenylalanine (cytosol to extracellular)

  Catalysed by ACOT7, BAAT, THEM4, ACOT1 and 5 morecytosol, mitochondrial matrix, extracellular spaceOne of 28 routes

• N(1)-acetylspermineReach from here →
  1. (9E)-octadecenoyl-CoA hydrolase
  2. diamine N-acetyltransferase (N1-acetylspermidine)
  3. N(1)-acetylspermine + O2 + H2O = 3-acetamidopropanal + spermidine + H2O2

  Catalysed by ACOT7, BAAT, THEM4, ACOT1 and 4 morecytosol

• 3-hydroxy-L-kynurenineReach from here →
  1. (9E)-octadecenoyl-CoA hydrolase
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. 3-hydroxy-L-kynurenine + H2O = 3-hydroxyanthranilate + L-alanine + H(+)

  Catalysed by ACOT7, BAAT, THEM4, ACOT1 and 2 morecytosol, 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. (9E)-octadecenoyl-CoA hydrolase
  2. N-acetylglutamate synthase (N-acetyl-L-cysteine)
  3. L-glutamate:L-cysteine gamma-ligase (ADP-forming)

  Catalysed by ACOT7, BAAT, THEM4, ACOT1 and 4 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. (9E)-octadecenoyl-CoA hydrolase
  2. N-acetylglutamate synthase (N-acetyl-L-cystathionine)
  3. L-homocysteine + L-serine = L,L-cystathionine + H2O

  Catalysed by ACOT7, BAAT, THEM4, ACOT1 and 3 morecytosol, mitochondrial matrixOne of 2 routes

• S-methyl-L-methionineReach from here →
  1. (9E)-octadecenoyl-CoA hydrolase
  2. N-acetylglutamate synthase (N-acetylmethionine)
  3. S-methyl-L-methionine + L-homocysteine = 2 L-methionine + H(+)

  Catalysed by ACOT7, BAAT, THEM4, ACOT1 and 3 morecytosol, mitochondrial matrix

• 3-oxosphinganineReach from here →
  1. (9E)-octadecenoyl-CoA hydrolase
  2. Palmitate:CoA ligase (AMP-forming)
  3. Palmitoyl-CoA:L-serine C-palmitoyltransferase (decarboxylating)

  Catalysed by ACOT7, BAAT, THEM4, ACOT1 and 12 morecytosol

• 1-hexadecanoylglycerone 3-phosphateReach from here →
  1. (9E)-octadecenoyl-CoA hydrolase
  2. Palmitate:CoA ligase (AMP-forming)
  3. glyceronephosphate O-acyltransferase (DHAP)

  Catalysed by ACOT7, BAAT, THEM4, ACOT1 and 10 morecytosol, peroxisome

• L-tyrosineReach from here →
  1. (9E)-octadecenoyl-CoA hydrolase
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. L-tyrosine + glyoxylate = 3-(4-hydroxyphenyl)pyruvate + glycine

  Catalysed by ACOT7, BAAT, THEM4, ACOT1 and 5 morecytosol, mitochondrial matrix

• N(1)-acetylspermidineReach from here →
  1. (9E)-octadecenoyl-CoA hydrolase
  2. diamine N-acetyltransferase (N1-acetylspermidine)
  3. spermidine + acetyl-CoA = N(1)-acetylspermidine + CoA + H(+)

  Catalysed by ACOT7, BAAT, THEM4, ACOT1 and 3 morecytosol

• N(omega),N(omega)-dimethyl-L-arginineReach from here →
  1. (9E)-octadecenoyl-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 ACOT7, BAAT, THEM4, ACOT1 and 5 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. (9E)-octadecenoyl-CoA hydrolase
  2. diamine N-acetyltransferase (N1-acetylspermine)
  3. spermidine:oxygen oxidoreductase (spermidine-forming)

  Catalysed by ACOT7, BAAT, THEM4, ACOT1 and 4 morecytosol

• trans-4-hydroxy-L-prolineReach from here →
  1. (9E)-octadecenoyl-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 ACOT7, BAAT, THEM4, ACOT1 and 2 morecytosol, 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. (9E)-octadecenoyl-CoA hydrolase
  2. diamine N-acetyltransferase (N1-acetylspermidine)
  3. N8-acetylspermidine to spermidine conversion

  Catalysed by ACOT7, BAAT, THEM4, ACOT1 and 3 morecytosolOne of 3 routes

• N(1),N(12)-diacetylspermineReach from here →
  1. (9E)-octadecenoyl-CoA hydrolase
  2. N1,N12-diacetylspermine to N1-acetylspermine conversion
  3. N1,N12-diacetylspermine to N1-acetylspermine conversion

  Catalysed by ACOT7, BAAT, THEM4, ACOT1 and 1 morecytosolOne of 2 routes

• S-sulfanyl-L-cysteineReach from here →
  1. (9E)-octadecenoyl-CoA hydrolase
  2. N-acetylglutamate synthase (N-acetyl-L-cysteine)
  3. 2 L-cysteine = S-sulfanyl-L-cysteine + L-alanine

  Catalysed by ACOT7, BAAT, THEM4, ACOT1 and 3 morecytosol, mitochondrial matrix

• (3S)-citramalyl-CoAReach from here →
  1. (9E)-octadecenoyl-CoA hydrolase
  2. Itaconate:CoA ligase (GDP-forming)
  3. (3S)-citramalyl-CoA = itaconyl-CoA + H2O

  Catalysed by ACOT7, BAAT, THEM4, ACOT1 and 5 morecytosol, mitochondrial matrix

• phosphoenolpyruvateReach from here →
  1. (9E)-octadecenoyl-CoA hydrolase
  2. ATP citrate lyase (citrate)
  3. oxaloacetate + GTP = phosphoenolpyruvate + GDP + CO2

  Catalysed by ACOT7, BAAT, THEM4, ACOT1 and 4 morecytosol

• L-methionine (S)-S-oxideReach from here →
  1. (9E)-octadecenoyl-CoA hydrolase
  2. N-acetylglutamate synthase (N-acetylmethionine)
  3. [thioredoxin]-disulfide + L-methionine + H2O = L-methionine (S)-S-oxide + [thioredoxin]-dithiol

  Catalysed by ACOT7, BAAT, THEM4, ACOT1 and 3 morecytosol, mitochondrial matrix

• L-methionine (R)-S-oxideReach from here →
  1. (9E)-octadecenoyl-CoA hydrolase
  2. N-acetylglutamate synthase (N-acetylmethionine)
  3. [thioredoxin]-disulfide + L-methionine + H2O = L-methionine (R)-S-oxide + [thioredoxin]-dithiol

  Catalysed by ACOT7, BAAT, THEM4, ACOT1 and 5 morecytosol, mitochondrial matrix

• N-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-glycineReach from here →
  1. (9E)-octadecenoyl-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 ACOT7, BAAT, THEM4, ACOT1 and 4 morecytosol, mitochondrial matrixOne of 3 routes