CHEBI:1146900

Three steps

• a (3S)-3-hydroxyacyl-CoAReach from here →
  1. acyl-CoA:sphingosine N-acyltransferase
  2. an acyl-CoA + acetyl-CoA = a 3-oxoacyl-CoA + CoA
  3. a (3S)-3-hydroxyacyl-CoA + NAD(+) = a 3-oxoacyl-CoA + NADH + H(+)

  Catalysed by ASAH1, ACER2, ACER1, ASAH2 and 7 moreGolgi apparatus

• 2-methyl-3-oxobutanoyl-CoAReach from here →
  1. (S)-methylmalonyl-CoA hydrolase
  2. (S)-methylmalonyl-CoA + H(+) = propanoyl-CoA + CO2
  3. propanoyl-CoA + acetyl-CoA = 2-methyl-3-oxobutanoyl-CoA + CoA

  Catalysed by ECHDC1, ACAT1mitochondrial matrix

• benzoyl-CoAReach from here →
  1. glycine N-acyltransferase (N-arachidonoylglycine)
  2. Hippurate (Benzoylglycinate) Formation
  3. benzoyl-CoA + glycine = N-benzoylglycine + CoA + H(+)

  Catalysed by GLYAT, GLYATL2, GLYATL1mitochondrial matrix

• choloyl-CoAReach from here →
  1. propanoyl-CoA C-acyltransferase
  2. choloyl-CoA hydrolase
  3. cholate + ATP + CoA = choloyl-CoA + AMP + diphosphate

  Catalysed by ACAA1, SCP2, MYO5B, ACOT8 and 1 moreperoxisome, cytosol

• prostaglandin E1Reach from here →
  1. N-acetyl-LTE4 to leukotriene E4 conversion
  2. transport of GSH and leukotriene E4 (cytosol to extracellular)
  3. transport of GSH and prostaglandin E1 (cytosol to extracellular)

  Catalysed by ZDHHC11B, NAA10, ESCO2, ESCO1 and 30 morecytosol, extracellular spaceOne of 4 routes

• prostaglandin I2Reach from here →
  1. N-acetyl-LTE4 to leukotriene E4 conversion
  2. transport of GSH and leukotriene E4 (cytosol to extracellular)
  3. transport of GSH and prostaglandin I2 (cytosol to extracellular)

  Catalysed by ZDHHC11B, NAA10, ESCO2, ESCO1 and 30 morecytosol, extracellular spaceOne of 4 routes

• prostaglandin F2alphaReach from here →
  1. N-acetyl-LTE4 to leukotriene E4 conversion
  2. transport of GSH and leukotriene E4 (cytosol to extracellular)
  3. transport of GSH and prostaglandin F2alpha (cytosol to extracellular)

  Catalysed by ZDHHC11B, NAA10, ESCO2, ESCO1 and 30 morecytosol, extracellular spaceOne of 6 routes

• prostaglandin H2Reach from here →
  1. Carnitine O-Palmitoyltransferase
  2. Utilized Transport
  3. prostaglandin-endoperoxide synthase (arachidonate)

  Catalysed by CPT1A, CPT1C, CPT1B, PTGS1 and 1 morecytosol, endoplasmic reticulumOne of 9 routes

• prostaglandin D2Reach from here →
  1. N-acetyl-LTE4 to leukotriene E4 conversion
  2. transport of GSH and leukotriene E4 (cytosol to extracellular)
  3. transport of GSH and prostaglandin D2 (cytosol to extracellular)

  Catalysed by ZDHHC11B, NAA10, ESCO2, ESCO1 and 30 morecytosol, extracellular spaceOne of 4 routes

• (15S)-hydroxy-(5Z,8Z,11Z,13E)-eicosatetraenoateReach from here →
  1. N-acetyl-LTE4 to leukotriene E4 conversion
  2. transport of GSH and leukotriene E4 (cytosol to extracellular)
  3. Glutathione: 15-HPETE oxidoreductase

  Catalysed by ZDHHC11B, NAA10, ESCO2, ESCO1 and 38 morecytosol, extracellular spaceOne of 3 routes

• (12S)-hydroperoxy-(5Z,8Z,10E,14Z)-eicosatetraenoateReach from here →
  1. Carnitine O-Palmitoyltransferase
  2. Utilized Transport
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + O2 = (12S)-hydroperoxy-(5Z,8Z,10E,14Z)-eicosatetraenoate

  Catalysed by CPT1A, CPT1C, CPT1B, ALOX5 and 2 morecytosol, endoplasmic reticulum

• (15S)-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoateReach from here →
  1. Carnitine O-Palmitoyltransferase
  2. Utilized Transport
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + O2 = (15S)-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoate

  Catalysed by CPT1A, CPT1C, CPT1B, ALOX15B and 2 morecytosol, endoplasmic reticulum

• (5S)-hydroperoxy-(6E,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. Carnitine O-Palmitoyltransferase
  2. Utilized Transport
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + O2 = (5S)-hydroperoxy-(6E,8Z,11Z,14Z)-eicosatetraenoate

  Catalysed by CPT1A, CPT1C, CPT1B, ALOX5cytosol, endoplasmic reticulum

• 5-formimidoyltetrahydrofolateReach from here →
  1. glycine N-acyltransferase (N-arachidonoylglycine)
  2. 5,10-Methylenetetrahydrofolate:glycine hydroxymethyltransferase
  3. 5-Formiminotetrahydrofolate:L-glutamate N-formiminotransferase

  Catalysed by GLYAT, GLYATL2, GLYATL1, SHMT1 and 1 moremitochondrial matrix, cytosolOne of 2 routes

• leukotriene A4Reach from here →
  1. Carnitine O-Palmitoyltransferase
  2. Utilized Transport
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + O2 = leukotriene A4 + H2O

  Catalysed by CPT1A, CPT1C, CPT1B, ALOX5cytosol, endoplasmic reticulumOne of 6 routes

• (13S)-hydroperoxy-(9Z,11E)-octadecadienoateReach from here →
  1. Carnitine O-Palmitoyltransferase
  2. Utilized Transport
  3. Linoleate:oxygen 13-oxidoreductase

  Catalysed by CPT1A, CPT1C, CPT1B, ALOX15B and 1 morecytosol, endoplasmic reticulumOne of 2 routes

• 2-(N(omega)-L-arginino)succinateReach from here →
  1. glycine N-acyltransferase (N-arachidonoylglycine)
  2. transport of arginine and glycine (cytosol to extracellular)
  3. 2-(Nomega-L-arginino)succinate arginine-lyase (fumarate-forming)

  Catalysed by GLYAT, GLYATL2, GLYATL1, SLC7A6 and 1 moremitochondrial matrix, extracellular space, cytosolOne of 6 routes

• (R)-S-lactoylglutathioneReach from here →
  1. N-acetyl-LTE4 to leukotriene E4 conversion
  2. transport of GSH and leukotriene E4 (cytosol to extracellular)
  3. (R)-S-Lactoylglutathione methylglyoxal-lyase (isomerizing)

  Catalysed by ZDHHC11B, NAA10, ESCO2, ESCO1 and 31 morecytosol, extracellular spaceOne of 3 routes

• carnosineReach from here →
  1. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  2. beta-alanine(out) + L-alanine(in) = beta-alanine(in) + L-alanine(out)
  3. beta-alanine + L-histidine + ATP = carnosine + ADP + phosphate + H(+)

  Catalysed by SLC7A10, CARNS1mitochondrial matrix, inner side of the membrane, outer side of the membrane

• 4-guanidinobutanoateReach from here →
  1. glycine N-acyltransferase (N-arachidonoylglycine)
  2. transport of arginine and glycine (cytosol to extracellular)
  3. 4-aminobutanoate + L-arginine = 4-guanidinobutanoate + L-ornithine

  Catalysed by GLYAT, GLYATL2, GLYATL1, SLC7A6 and 1 moremitochondrial matrix, extracellular space, cytosol

• 2-oxoadipateReach from here →
  1. glycine N-acyltransferase (N-arachidonoylglycine)
  2. glycine + 2-oxoglutarate = glyoxylate + L-glutamate
  3. L-2-aminoadipate + glyoxylate = 2-oxoadipate + glycine

  Catalysed by GLYAT, GLYATL2, GLYATL1, AADATmitochondrial matrix

• L-dopaReach from here →
  1. glycine N-acyltransferase (N-arachidonoylglycine)
  2. transport of glycine and phenylalanine (cytosol to extracellular)
  3. L-dopa(out) + L-phenylalanine(in) = L-dopa(in) + L-phenylalanine(out)

  Catalysed by GLYAT, GLYATL2, GLYATL1, SLC7A5 and 1 moremitochondrial matrix, extracellular space, cytosol, inner side of the membrane, outer side of the membraneOne of 3 routes

• a long-chain fatty acidReach from here →
  1. acyl-CoA:sphingosine N-acyltransferase
  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 ASAH1, ACER2, ACER1, ASAH2 and 2 moreGolgi apparatus

• (R)-2-hydroxyoctadecanoateReach from here →
  1. long-chain-fatty-acid-CoA ligase (stearate)
  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 SLC27A2, ACSL4, ACSL3, ACSL1 and 9 morecytosol

• N(6)-(1,2-dicarboxyethyl)-AMPReach from here →
  1. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  2. oxaloacetate + L-alanine = L-aspartate + pyruvate
  3. IMP:L-aspartate ligase (GDP-forming)

  Catalysed by AGXT2, ADSS2, ADSS1mitochondrial matrix, cytosolOne of 2 routes

• 3-guanidinopropanoateReach from here →
  1. glycine N-acyltransferase (N-arachidonoylglycine)
  2. transport of arginine and glycine (cytosol to extracellular)
  3. beta-alanine + L-arginine = 3-guanidinopropanoate + L-ornithine

  Catalysed by GLYAT, GLYATL2, GLYATL1, SLC7A6 and 1 moremitochondrial matrix, extracellular space, cytosolOne of 2 routes

• L-histidineReach from here →
  1. bile acid-CoA:amino acid N-acyltransferase (taurodeoxycholate)
  2. taurine + L-arginine = taurocyamine + L-ornithine
  3. L-histidine(in) + L-ornithine(out) + H(+)(in) = L-histidine(out) + L-ornithine(in) + H(+)(out)

  Catalysed by BAAT, GATM, SLC25A2cytosol, inner side of the membrane, outer side of the membraneOne of 7 routes

• sn-glycerol 3-phosphateReach from here →
  1. Palmitate:CoA ligase (AMP-forming)
  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 SLC27A2, ACSL4, ACSL3, ACSL1 and 11 morecytosol

• ethanolamineReach from here →
  1. long-chain-fatty-acid-CoA ligase (stearate)
  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 SLC27A2, ACSL4, ACSL3, ACSL1 and 5 morecytosolOne of 5 routes

• D-ornithineReach from here →
  1. bile acid-CoA:amino acid N-acyltransferase (taurodeoxycholate)
  2. taurine + L-arginine = taurocyamine + L-ornithine
  3. D-ornithine(in) + L-ornithine(out) = D-ornithine(out) + L-ornithine(in)

  Catalysed by BAAT, GATM, SLC25A2cytosol, inner side of the membrane, outer side of the membraneOne of 2 routes

• an N-acylsphing-4-enine 1-phosphateReach from here →
  1. acyl-CoA:sphingosine N-acyltransferase
  2. sphing-4-enine + a fatty acyl-CoA = an N-acylsphing-4-enine + CoA + H(+)
  3. an N-acylsphing-4-enine + ATP = an N-acylsphing-4-enine 1-phosphate + ADP + H(+)

  Catalysed by ASAH1, ACER2, ACER1, ASAH2 and 8 moreGolgi apparatus

• S-formylglutathioneReach from here →
  1. N-acetyl-LTE4 to leukotriene E4 conversion
  2. transport of GSH and leukotriene E4 (cytosol to extracellular)
  3. alcohol dehydrogenase (formaldehyde)

  Catalysed by ZDHHC11B, NAA10, ESCO2, ESCO1 and 35 morecytosol, extracellular spaceOne of 2 routes

• 2-methyl-3-oxopropanoateReach from here →
  1. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  2. (R)-3-Amino-2-methylpropanoate:pyruvate aminotransferase
  3. (R)-3-amino-2-methylpropanoate + pyruvate = 2-methyl-3-oxopropanoate + L-alanine

  Catalysed by AGXT2mitochondrial matrix

• a 1,2-diacyl-sn-glycero-3-phospho-(1D-myo-inositol-5-phosphate)Reach from here →
  1. acyl-CoA:sphingosine N-acyltransferase
  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 ASAH1, ACER2, ACER1, ASAH2 and 3 moreGolgi apparatus

• sphinganineReach from here →
  1. Palmitate:CoA ligase (AMP-forming)
  2. Palmitoyl-CoA:L-serine C-palmitoyltransferase (decarboxylating)
  3. sphinganine + NADP(+) = 3-oxosphinganine + NADPH + H(+)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 8 morecytosolOne of 3 routes

• hypotaurineReach from here →
  1. N-acetylglutamate synthase (N-acetyl-L-cysteine)
  2. L-Cysteine:oxygen oxidoreductase
  3. 3-sulfino-L-alanine + H(+) = hypotaurine + CO2

  Catalysed by NAGS, CDO1, GADL1, CSADmitochondrial matrix, cytosol

• a 2-acyl-sn-glycero-3-phosphocholineReach from here →
  1. acyl-CoA:sphingosine N-acyltransferase
  2. 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(+)
  3. N-(acetyl)-sphing-4-enine + a 1,2-diacyl-sn-glycero-3-phosphocholine = 1-O-acyl-N-(acetyl)-sphing-4-enine + a 2-acyl-sn-glycero-3-phosphocholine

  Catalysed by ASAH1, ACER2, ACER1, ASAH2 and 2 moreGolgi apparatusOne of 13 routes

• CDP-ethanolamineReach from here →
  1. acyl-CoA:sphingosine N-acyltransferase
  2. Acyl-CoA:1-alkenylglycerophosphoethanolamine O-acyltransferase
  3. ethanolaminephosphotransferase (1-alkenyl-2-acylglycerol)

  Catalysed by ASAH1, ACER2, ACER1, ASAH2 and 6 moreGolgi apparatus, cytosol

• dehydroepiandrosterone 3-sulfateReach from here →
  1. Butanoate:CoA ligase (AMP-forming)
  2. butanoyl-CoA + H2O = butanoate + CoA + H(+)
  3. dehydroepiandrosterone 3-sulfate(in) + butanoate(out) = dehydroepiandrosterone 3-sulfate(out) + butanoate(in)

  Catalysed by ACSM4, ACSM1, ACSM2A, ACSM3 and 9 morecytosol, inner side of the membrane, outer side of the membraneOne of 6 routes

• L-dopaquinoneReach from here →
  1. glycine N-acyltransferase (N-arachidonoylglycine)
  2. transport of glycine and tyrosine (cytosol to extracellular)
  3. L-Tyrosine,L-dopa:oxygen oxidoreductase

  Catalysed by GLYAT, GLYATL2, GLYATL1, SLC7A5 and 1 moremitochondrial matrix, extracellular space, cytosolOne of 2 routes

• L-saccharopineReach from here →
  1. glycine N-acyltransferase (N-arachidonoylglycine)
  2. transport of glycine and lysine (cytosol to extracellular)
  3. N6-(L-1,3-Dicarboxypropyl)-L-lysine:NADP+ oxidoreductase (L-lysine-forming)

  Catalysed by GLYAT, GLYATL2, GLYATL1, SLC7A6 and 1 moremitochondrial matrix, extracellular space, cytosol

• dimethylamineReach from here →
  1. glycine N-acyltransferase (N-arachidonoylglycine)
  2. N(omega),N(omega)-dimethyl-L-arginine + glyoxylate = 5-(3,3-dimethylguanidino)-2-oxopentanoate + glycine
  3. Nomega,Nomega'-dimethyl-L-arginine dimethylamidohydrolase

  Catalysed by GLYAT, GLYATL2, GLYATL1, AGXT2 and 1 moremitochondrial matrix, cytosolOne of 2 routes

• L-glutamate 5-semialdehydeReach from here →
  1. bile acid-CoA:amino acid N-acyltransferase (taurodeoxycholate)
  2. taurine + L-arginine = taurocyamine + L-ornithine
  3. L-ornithine + 2-oxoglutarate = L-glutamate 5-semialdehyde + L-glutamate

  Catalysed by BAAT, GATM, OATcytosol

• N(4)-(beta-N-acetyl-D-glucosaminyl)-L-asparagineReach from here →
  1. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  2. oxaloacetate + L-alanine = L-aspartate + pyruvate
  3. N(4)-(beta-N-acetyl-D-glucosaminyl)-L-asparagine + H2O = N-acetyl-beta-D-glucosaminylamine + L-aspartate + H(+)

  Catalysed by AGXT2, AGAmitochondrial matrix

• a 1,2-diacyl-sn-glycero-3-phospho-(1D-myo-inositol-3-phosphate)Reach from here →
  1. acyl-CoA:sphingosine N-acyltransferase
  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 ASAH1, ACER2, ACER1, ASAH2 and 9 moreGolgi apparatus

• porphobilinogenReach from here →
  1. glycine N-acyltransferase (N-arachidonoylglycine)
  2. succinyl-CoA:glycine C-succinyltransferase (decarboxylating)
  3. 5-aminolevulinate hydro-lyase (adding 5-aminolevulinate and cyclizing

  Catalysed by GLYAT, GLYATL2, GLYATL1, ALAS1 and 3 moremitochondrial matrix, cytosolOne of 2 routes

• a 1-acyl-sn-glycero-3-phosphocholineReach from here →
  1. long-chain-fatty-acid-CoA ligase ((6Z,9Z)-octadecadienoic acid)
  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 SLC27A2, ACSL4, ACSL3, ACSL1 and 6 morecytosolOne of 16 routes

• a 1,2-diacyl-sn-glycero-3-phospho-(1D-myo-inositol 4-phosphate)Reach from here →
  1. acyl-CoA:sphingosine N-acyltransferase
  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 ASAH1, ACER2, ACER1, ASAH2 and 2 moreGolgi apparatus, inner side of the membrane, outer side of the membraneOne of 5 routes

• 6-amino-2-oxohexanoateReach from here →
  1. glycine N-acyltransferase (N-arachidonoylglycine)
  2. transport of glycine and lysine (cytosol to extracellular)
  3. L-lysine:oxygen 2-oxidoreductase (deaminating)

  Catalysed by GLYAT, GLYATL2, GLYATL1, SLC7A6mitochondrial matrix, extracellular space, cytosol, peroxisome

• phosphoethanolamineReach from here →
  1. acyl-CoA:sphingosine N-acyltransferase
  2. sphing-4-enine + ATP = sphing-4-enine 1-phosphate + ADP + H(+)
  3. sphing-4-enine 1-phosphate = (2E)-hexadecenal + phosphoethanolamine

  Catalysed by ASAH1, ACER2, ACER1, ASAH2 and 3 moreGolgi apparatusOne of 2 routes