CHEBI:1146900

Three steps

• N-(acetyl)-sphing-4-enine-1-phosphateReach 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 + ATP = N-(acetyl)-sphing-4-enine-1-phosphate + ADP + H(+)

  Catalysed by ASAH1, ACER2, ACER1, ASAH2 and 2 moreGolgi apparatus

• 1-decanoyl-2-(9Z-octadecenoyl)-glycerolReach from here →
  1. long-chain-fatty-acid-CoA ligase (stearate)
  2. octadecanoyl-CoA + 2 Fe(II)-[cytochrome b5] + O2 + 2 H(+) = (9Z)-octadecenoyl-CoA + 2 Fe(III)-[cytochrome b5] + 2 H2O
  3. 1-decanoylglycerol + (9Z)-octadecenoyl-CoA = 1-decanoyl-2-(9Z-octadecenoyl)-glycerol + CoA

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 6 morecytosol

• (3S)-hydroxy-(9Z-octadecenoyl)-CoAReach from here →
  1. Transport of octadecenoyl-CoA into Mitochondrial Matrix
  2. medium-chain acyl-CoA dehydrogenase (oleoyl-CoA)
  3. hydroxyacyl-CoA dehydrogenase trifunctional multienzyme complex

  Catalysed by CPT1A, CPT1C, CPT1B, ACADM and 4 morecytosol, mitochondrial matrixOne of 3 routes

• 3-methylmalateReach from here →
  1. (S)-methylmalonyl-CoA hydrolase
  2. (S)-methylmalonyl-CoA + H(+) = propanoyl-CoA + CO2
  3. propanoyl-CoA + glyoxylate + H2O = 3-methylmalate + CoA + H(+)

  Catalysed by ECHDC1, CLYBLmitochondrial matrixOne of 2 routes

• (5S)-hydroxy-(6E,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. glycine N-acyltransferase (N-arachidonoylglycine)
  2. gamma-L-glutamyl-L-cysteine + glycine + ATP = glutathione + ADP + phosphate + H(+)
  3. (5S)-hydroperoxy-(6E,8Z,11Z,14Z)-eicosatetraenoate + 2 glutathione = (5S)-hydroxy-(6E,8Z,11Z,14Z)-eicosatetraenoate + glutathione disulfide + H2O

  Catalysed by GLYAT, GLYATL2, GLYATL1, GSS and 6 moremitochondrial matrix

• Se-methylselenocysteineReach from here →
  1. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  2. L-selenocysteine selenide-lyase (L-alanine-forming)
  3. S-Adenosyl-L-methionine:thiol S-methyltransferase

  Catalysed by SCLYmitochondrial matrix, cytosol

• (12S)-hydroxy-(5Z,8Z,10E,14Z)-eicosatetraenoateReach from here →
  1. glycine N-acyltransferase (N-arachidonoylglycine)
  2. gamma-L-glutamyl-L-cysteine + glycine + ATP = glutathione + ADP + phosphate + H(+)
  3. (12S)-hydroperoxy-(5Z,8Z,10E,14Z)-eicosatetraenoate + 2 glutathione = (12S)-hydroxy-(5Z,8Z,10E,14Z)-eicosatetraenoate + glutathione disulfide + H2O

  Catalysed by GLYAT, GLYATL2, GLYATL1, GSS and 2 moremitochondrial matrix

• thromboxane B2Reach 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 thromboxane B2 (cytosol to extracellular)

  Catalysed by ZDHHC11B, NAA10, ESCO2, ESCO1 and 29 morecytosol, extracellular spaceOne of 4 routes

• (12S)-hydroperoxy-(5Z,8Z,10E,14Z,17Z)-eicosapentaenoateReach from here →
  1. long-chain-fatty-acid-CoA ligase (EPA)
  2. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA hydrolase
  3. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate + O2 = (12S)-hydroperoxy-(5Z,8Z,10E,14Z,17Z)-eicosapentaenoate

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 8 morecytosol

• an S-substituted glutathioneReach from here →
  1. glycine N-acyltransferase (N-arachidonoylglycine)
  2. gamma-L-glutamyl-L-cysteine + glycine + ATP = glutathione + ADP + phosphate + H(+)
  3. RX + glutathione = an S-substituted glutathione + a halide anion + H(+)

  Catalysed by GLYAT, GLYATL2, GLYATL1, GSS and 23 moremitochondrial matrixOne of 2 routes

• (18R)-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. Carnitine O-Palmitoyltransferase
  2. Utilized Transport
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + reduced [NADPH--hemoprotein reductase] + O2 = (18R)-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by CPT1A, CPT1C, CPT1B, CYP4F8cytosol, endoplasmic reticulum

• prostaglandin H1Reach from here →
  1. bile acid-CoA:amino acid N-acyltransferase (taurodeoxycholate)
  2. uridine(34) in tRNA + 5,10-methylenetetrahydrofolate + taurine + GTP + A + H2O = 5-taurinomethyluridine(34) in tRNA + 7,8-dihydrofolate + GDP + AH2 + phosphate + H(+)
  3. prostaglandin G1 + AH2 = prostaglandin H1 + A + H2O

  Catalysed by BAAT, MTO1, PTGS2cytosol

• (5S,11R)-dihydroxy-(6E,8Z,12E,14Z)-eicosatetraenoateReach from here →
  1. bile acid-CoA:amino acid N-acyltransferase (taurodeoxycholate)
  2. uridine(34) in tRNA + 5,10-methylenetetrahydrofolate + taurine + GTP + A + H2O = 5-taurinomethyluridine(34) in tRNA + 7,8-dihydrofolate + GDP + AH2 + phosphate + H(+)
  3. (5S)-hydroxy-(6E,8Z,11Z,14Z)-eicosatetraenoate + AH2 + O2 = (5S,11R)-dihydroxy-(6E,8Z,12E,14Z)-eicosatetraenoate + A + H2O

  Catalysed by BAAT, MTO1, PTGS2cytosol

• (5S,15R)-dihydroxy-(6E,8Z,11Z,13E)-eicosatetraenoateReach from here →
  1. bile acid-CoA:amino acid N-acyltransferase (taurodeoxycholate)
  2. uridine(34) in tRNA + 5,10-methylenetetrahydrofolate + taurine + GTP + A + H2O = 5-taurinomethyluridine(34) in tRNA + 7,8-dihydrofolate + GDP + AH2 + phosphate + H(+)
  3. (5S)-hydroxy-(6E,8Z,11Z,14Z)-eicosatetraenoate + AH2 + O2 = (5S,15R)-dihydroxy-(6E,8Z,11Z,13E)-eicosatetraenoate + A + H2O

  Catalysed by BAAT, MTO1, PTGS2cytosol

• (5S,15S)-dihydroxy-(6E,8Z,11Z,13E)-eicosatetraenoateReach from here →
  1. bile acid-CoA:amino acid N-acyltransferase (taurodeoxycholate)
  2. uridine(34) in tRNA + 5,10-methylenetetrahydrofolate + taurine + GTP + A + H2O = 5-taurinomethyluridine(34) in tRNA + 7,8-dihydrofolate + GDP + AH2 + phosphate + H(+)
  3. (5S)-hydroxy-(6E,8Z,11Z,14Z)-eicosatetraenoate + AH2 + O2 = (5S,15S)-dihydroxy-(6E,8Z,11Z,13E)-eicosatetraenoate + A + H2O

  Catalysed by BAAT, MTO1, PTGS2cytosol

• 17R-hydroxy-(4Z,7Z,10Z,13Z,15E,19Z)-docosahexaenoateReach from here →
  1. long-chain-fatty-acid-CoA ligase (DHA)
  2. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoyl-CoA hydrolase
  3. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoate + AH2 + O2 = 17R-hydroxy-(4Z,7Z,10Z,13Z,15E,19Z)-docosahexaenoate + A + H2O

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 7 morecytosolOne of 2 routes

• 13-hydroxy-(4Z,7Z,10Z,14E,16Z,19Z)-docosahexaenoateReach from here →
  1. long-chain-fatty-acid-CoA ligase (DHA)
  2. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoyl-CoA hydrolase
  3. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoate + AH2 + O2 = 13-hydroxy-(4Z,7Z,10Z,14E,16Z,19Z)-docosahexaenoate + A + H2O

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 7 morecytosolOne of 2 routes

• (18R)-hydroxy-(5Z,8Z,11Z,14Z,16E)-eicosapentaenoateReach from here →
  1. long-chain-fatty-acid-CoA ligase (EPA)
  2. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA hydrolase
  3. prostaglandin-endoperoxide synthase (EPA)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 9 morecytosolOne of 3 routes

• (15R)-hydroxy-(5Z,8Z,11Z,13E,17Z)-eicosapentaenoateReach from here →
  1. long-chain-fatty-acid-CoA ligase (EPA)
  2. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA hydrolase
  3. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate + AH2 + O2 = (15R)-hydroxy-(5Z,8Z,11Z,13E,17Z)-eicosapentaenoate + A + H2O

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 8 morecytosolOne of 2 routes

• (11R)-hydroxy-(5Z,8Z,12E,14Z,17Z)-eicosapentaenoateReach from here →
  1. long-chain-fatty-acid-CoA ligase (EPA)
  2. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA hydrolase
  3. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate + AH2 + O2 = (11R)-hydroxy-(5Z,8Z,12E,14Z,17Z)-eicosapentaenoate + A + H2O

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 8 morecytosolOne of 2 routes

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

  Catalysed by CPT1A, CPT1C, CPT1B, ALOX15Bcytosol, endoplasmic reticulum

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

  Catalysed by CPT1A, CPT1C, CPT1B, ALOX15Bcytosol, endoplasmic reticulum

• 13-hydroperoxy-(9Z,11E)-octadecadienoateReach from here →
  1. long-chain-fatty-acid-CoA ligase ((6Z,9Z)-octadecadienoic acid)
  2. (9Z,12Z)-octadecadienoyl-CoA + H2O = (9Z,12Z)-octadecadienoate + CoA + H(+)
  3. (9Z,12Z)-octadecadienoate + O2 = 13-hydroperoxy-(9Z,11E)-octadecadienoate

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 9 morecytosol

• 13R-hydroxy-(7Z,10Z,14E,16Z,19Z)-docosapentaenoateReach from here →
  1. long-chain-fatty-acid-CoA ligase (DPA)
  2. (7Z,10Z,13Z,16Z,19Z)-docosapentaenoyl-CoA hydrolase
  3. (7Z,10Z,13Z,16Z,19Z)-docosapentaenoate + AH2 + O2 = 13R-hydroxy-(7Z,10Z,14E,16Z,19Z)-docosapentaenoate + A + H2O

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 7 morecytosolOne of 2 routes

• (13S)-hydroxy-(9Z,11E)-octadecadienoateReach from here →
  1. long-chain-fatty-acid-CoA ligase ((6Z,9Z)-octadecadienoic acid)
  2. (9Z,12Z)-octadecadienoyl-CoA + H2O = (9Z,12Z)-octadecadienoate + CoA + H(+)
  3. (9Z,12Z)-octadecadienoate + AH2 + O2 = (13S)-hydroxy-(9Z,11E)-octadecadienoate + A + H2O

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 10 morecytosolOne of 3 routes

• 3-deoxy-D-glycero-beta-D-galacto-non-2-ulopyranosonate 9-phosphateReach from here →
  1. ATP citrate lyase (citrate)
  2. oxaloacetate + GTP = phosphoenolpyruvate + GDP + CO2
  3. aldehydo-D-mannose 6-phosphate + phosphoenolpyruvate + H2O = 3-deoxy-D-glycero-beta-D-galacto-non-2-ulopyranosonate 9-phosphate + phosphate

  Catalysed by ACLY, PCK1, PCK2, NANScytosol

• 2-(1-hydroxyethyl)thiamine diphosphateReach from here →
  1. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  2. (R)-3-Amino-2-methylpropanoate:pyruvate aminotransferase
  3. pyruvate:thiamin diphosphate acetaldehydetransferase (decarboxylating)

  Catalysed by AGXT2, PDHA1, PDHB, PDHA2mitochondrial matrix