CHEBI:1146900

Three steps

• 9-hydroxy-(10E,12Z)-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 = 9-hydroxy-(10E,12Z)-octadecadienoate + A + H2O

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 9 morecytosolOne of 2 routes

• (8S,15S)-dihydroperoxy-(5Z,9E,11Z,13E)-eicosatetraenoateReach from here →
  1. Carnitine O-Palmitoyltransferase
  2. Utilized Transport
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + 2 O2 = (8S,15S)-dihydroperoxy-(5Z,9E,11Z,13E)-eicosatetraenoate

  Catalysed by CPT1A, CPT1C, CPT1B, ALOX15cytosol, endoplasmic reticulum

• (14R,15S)-dihydroperoxy-(5Z,8Z,10E,12E)-eicosatetraenoateReach from here →
  1. Carnitine O-Palmitoyltransferase
  2. Utilized Transport
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + 2 O2 = (14R,15S)-dihydroperoxy-(5Z,8Z,10E,12E)-eicosatetraenoate

  Catalysed by CPT1A, CPT1C, CPT1B, ALOX15cytosol, endoplasmic reticulum

• 19,20-epoxy-(4Z,7Z,10Z,13Z,16Z)-docosapentaenoateReach 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 + reduced [NADPH--hemoprotein reductase] + O2 = 19,20-epoxy-(4Z,7Z,10Z,13Z,16Z)-docosapentaenoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

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

• 16,17-epoxy-(4Z,7Z,10Z,13Z,19Z)-docosapentaenoateReach 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 + reduced [NADPH--hemoprotein reductase] + O2 = 16,17-epoxy-(4Z,7Z,10Z,13Z,19Z)-docosapentaenoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

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

• 13,14-epoxy-(4Z,7Z,10Z,16Z,19Z)-docosapentaenoateReach 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 + reduced [NADPH--hemoprotein reductase] + O2 = 13,14-epoxy-(4Z,7Z,10Z,16Z,19Z)-docosapentaenoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

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

• 10,11-epoxy-(4Z,7Z,13Z,16Z,19Z)-docosapentaenoateReach 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 + reduced [NADPH--hemoprotein reductase] + O2 = 10,11-epoxy-(4Z,7Z,13Z,16Z,19Z)-docosapentaenoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

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

• 19,20-epoxy-(7Z,10Z,13Z,16Z)-docosatetraenoateReach 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 + reduced [NADPH--hemoprotein reductase] + O2 = 19,20-epoxy-(7Z,10Z,13Z,16Z)-docosatetraenoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

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

• 16,17-epoxy-(7Z,10Z,13Z,19Z)-docosatetraenoateReach 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 + reduced [NADPH--hemoprotein reductase] + O2 = 16,17-epoxy-(7Z,10Z,13Z,19Z)-docosatetraenoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

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

• 13,14-epoxy-(7Z,10Z,16Z,19Z)-docosatetraenoateReach 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 + reduced [NADPH--hemoprotein reductase] + O2 = 13,14-epoxy-(7Z,10Z,16Z,19Z)-docosatetraenoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

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

• 10,11-epoxy-(7Z,13Z,16Z,19Z)-docosatetraenoateReach 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 + reduced [NADPH--hemoprotein reductase] + O2 = 10,11-epoxy-(7Z,13Z,16Z,19Z)-docosatetraenoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

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

• N-(9Z-octadecenoyl)-L-phenylalanineReach from here →
  1. Carnitine O-Palmitoyltransferase
  2. Utilized Transport
  3. L-phenylalanine + (9Z)-octadecenoate = N-(9Z-octadecenoyl)-L-phenylalanine + H2O

  Catalysed by CPT1A, CPT1C, CPT1B, PM20D1cytosol, endoplasmic reticulumOne of 2 routes

• N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-phenylalanineReach from here →
  1. Carnitine O-Palmitoyltransferase
  2. Utilized Transport
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + L-phenylalanine = N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-phenylalanine + H2O

  Catalysed by CPT1A, CPT1C, CPT1B, PM20D1cytosol, endoplasmic reticulumOne of 2 routes

• N-(9Z-octadecenoyl)-L-leucineReach from here →
  1. Carnitine O-Palmitoyltransferase
  2. Utilized Transport
  3. N-(9Z-octadecenoyl)-L-leucine + H2O = L-leucine + (9Z)-octadecenoate

  Catalysed by CPT1A, CPT1C, CPT1B, PM20D1cytosol, endoplasmic reticulumOne of 2 routes

• (19R,20S)-epoxy-(4Z,7Z,10Z,13Z,16Z)-docosapentaenoateReach 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 + reduced [NADPH--hemoprotein reductase] + O2 = (19R,20S)-epoxy-(4Z,7Z,10Z,13Z,16Z)-docosapentaenoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 13 morecytosol

• (19S,20R)-epoxy-(4Z,7Z,10Z,13Z,16Z)-docosapentaenoateReach 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 + reduced [NADPH--hemoprotein reductase] + O2 = (19S,20R)-epoxy-(4Z,7Z,10Z,13Z,16Z)-docosapentaenoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 12 morecytosol

• 8,9-epoxy-(5Z,11Z,14Z,17Z)-eicosatetraenoateReach 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 + reduced [NADPH--hemoprotein reductase] + O2 = 8,9-epoxy-(5Z,11Z,14Z,17Z)-eicosatetraenoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

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

• 11,12-epoxy-(5Z,8Z,14Z,17Z)-eicosatetraenoateReach 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 + reduced [NADPH--hemoprotein reductase] + O2 = 11,12-epoxy-(5Z,8Z,14Z,17Z)-eicosatetraenoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

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

• 14,15-epoxy-(5Z,8Z,11Z,17Z)-eicosatetraenoateReach 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 + reduced [NADPH--hemoprotein reductase] + O2 = 14,15-epoxy-(5Z,8Z,11Z,17Z)-eicosatetraenoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

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

• 11-hydroxy-(9Z,12Z)-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 + reduced [NADPH--hemoprotein reductase] + O2 = 11-hydroxy-(9Z,12Z)-octadecadienoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 10 morecytosol

• 7-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. Carnitine O-Palmitoyltransferase
  2. Utilized Transport
  3. unspecific monooxygenase (arachidonate)

  Catalysed by CPT1A, CPT1C, CPT1B, CYP1A1 and 25 morecytosol, endoplasmic reticulumOne of 2 routes

• 13-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. Carnitine O-Palmitoyltransferase
  2. Utilized Transport
  3. unspecific monooxygenase (arachidonate)

  Catalysed by CPT1A, CPT1C, CPT1B, CYP1A1 and 25 morecytosol, endoplasmic reticulumOne of 2 routes

• 13(S)-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 = 13(S)-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by CPT1A, CPT1C, CPT1B, CYP2C9cytosol, endoplasmic reticulum

• (13R)-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 + reduced [NADPH--hemoprotein reductase] + O2 = (13R)-hydroxy-(9Z,11E)-octadecadienoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

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

• chenodeoxycholoyl-24-O-(beta-D-glucuronate)Reach from here →
  1. Propanoyl-CoA:acetyl-CoA C-acyltransferase
  2. chenodeoxycholoyl-CoA hydrolase
  3. chenodeoxycholate + UDP-alpha-D-glucuronate = chenodeoxycholoyl-24-O-(beta-D-glucuronate) + UDP

  Catalysed by ACAA1, SCP2, MYO5B, ACOT7 and 4 moreperoxisome

• acetoacetateReach from here →
  1. Propanoate:CoA ligase (AMP-forming)
  2. Propanoyl-CoA hydrolase
  3. transport of acetoacetate and propanoate (cytosol to extracellular)

  Catalysed by ACSS3, ACSS2, ACSS1, ACOT7 and 5 morecytosol, extracellular spaceOne of 11 routes

• 16(R)-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. Carnitine O-Palmitoyltransferase
  2. Utilized Transport
  3. unspecific monooxygenase (arachidonate)

  Catalysed by CPT1A, CPT1C, CPT1B, CYP1A1 and 25 morecytosol, endoplasmic reticulum

• (13R)-S-glutathionyl-(14S)-hydroxy-(4Z,7Z,9E,11E,16Z,19Z)-docosahexaenoateReach from here →
  1. glycine N-acyltransferase (N-arachidonoylglycine)
  2. gamma-L-glutamyl-L-cysteine + glycine + ATP = glutathione + ADP + phosphate + H(+)
  3. (13S,14S)-epoxy-(4Z,7Z,9E,11E,16Z,19Z)-docosahexaenoate + glutathione = (13R)-S-glutathionyl-(14S)-hydroxy-(4Z,7Z,9E,11E,16Z,19Z)-docosahexaenoate

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

• 2-[(11R)-hydroxy-(5Z,8Z,12E,14Z)-eicosatetraenoyl]-sn-glycero-3-phosphocholineReach 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. 2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphocholine + AH2 + O2 = 2-[(11R)-hydroxy-(5Z,8Z,12E,14Z)-eicosatetraenoyl]-sn-glycero-3-phosphocholine + A + H2O

  Catalysed by BAAT, MTO1, PTGS2cytosol

• 2-[(15R)-hydroxy-(5Z,8Z,11Z,13E)-eicosatetraenoyl]-sn-glycero-3-phosphocholineReach 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. 2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphocholine + AH2 + O2 = 2-[(15R)-hydroxy-(5Z,8Z,11Z,13E)-eicosatetraenoyl]-sn-glycero-3-phosphocholine + A + H2O

  Catalysed by BAAT, MTO1, PTGS2cytosol

• 2-[(15S)-hydroxy-(5Z,8Z,11Z,13E)-eicosatetraenoyl]-sn-glycero-3-phosphocholineReach 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. 2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphocholine + AH2 + O2 = 2-[(15S)-hydroxy-(5Z,8Z,11Z,13E)-eicosatetraenoyl]-sn-glycero-3-phosphocholine + A + H2O

  Catalysed by BAAT, MTO1, PTGS2cytosol

• 2-(prostaglandin H2)-sn-glycero-3-phosphoethanolamineReach 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. 2-(prostaglandin G2)-sn-glycero-3-phosphoethanolamine + AH2 = 2-(prostaglandin H2)-sn-glycero-3-phosphoethanolamine + A + H2O

  Catalysed by BAAT, MTO1, PTGS2cytosol

• 2-(prostaglandin H2)-sn-glycero-3-phosphocholineReach 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. 2-(prostaglandin G2)-sn-glycero-3-phosphocholine + AH2 = 2-(prostaglandin H2)-sn-glycero-3-phosphocholine + A + H2O

  Catalysed by BAAT, MTO1, PTGS2cytosol

• N-(4-oxoglutaryl)-L-cysteinylglycineReach from here →
  1. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  2. gamma-glutamyltransferase (alanine)
  3. N-(4-oxoglutaryl)-L-cysteinylglycine + H2O = L-cysteinylglycine + 2-oxoglutarate

  Catalysed by GGTLC3, GGT1, GGT5, GGTLC2 and 3 moremitochondrial matrix, cytosol

• 13-cis-retinyl hexadecanoateReach from here →
  1. Carnitine O-Palmitoyltransferase
  2. (2E)-hexadecenoyl-CoA + NADPH + H(+) = hexadecanoyl-CoA + NADP(+)
  3. 13-cis-retinol + hexadecanoyl-CoA = 13-cis-retinyl hexadecanoate + CoA

  Catalysed by CPT1A, CPT1C, CPT1B, TECR and 1 morecytosolOne of 2 routes

• 9-cis-retinyl hexadecanoateReach from here →
  1. Carnitine O-Palmitoyltransferase
  2. (2E)-hexadecenoyl-CoA + NADPH + H(+) = hexadecanoyl-CoA + NADP(+)
  3. 9-cis-retinol + hexadecanoyl-CoA = 9-cis-retinyl hexadecanoate + CoA

  Catalysed by CPT1A, CPT1C, CPT1B, TECR and 1 morecytosolOne of 2 routes

• 1-O-(9Z-octadecenyl)-2,3-di-(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-O-(9Z-octadecyl)-3-(9Z-octadecenoyl)-glycerol + (9Z)-octadecenoyl-CoA = 1-O-(9Z-octadecenyl)-2,3-di-(9Z-octadecenoyl)glycerol + CoA

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

• beta-D-glucosyl-N-(9Z-octadecenoyl)-sphing-4E-enineReach from here →
  1. acyl-CoA:sphingosine N-acyltransferase
  2. N-(9Z-octadecenoyl)-sphing-4-enine + H2O = sphing-4-enine + (9Z)-octadecenoate
  3. beta-D-glucosyl-N-(9Z-octadecenoyl)-sphing-4E-enine + cholesterol = N-(9Z-octadecenoyl)-sphing-4-enine + cholesteryl 3-beta-D-glucoside

  Catalysed by ASAH1, ACER2, ACER1, ASAH2 and 3 moreGolgi apparatus

• an N-acyl-sphinga-4E,14Z-dienineReach 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 + 2 Fe(II)-[cytochrome b5] + O2 + 2 H(+) = an N-acyl-sphinga-4E,14Z-dienine + 2 Fe(III)-[cytochrome b5] + 2 H2O

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

• 3-sulfinopyruvateReach from here →
  1. N-acetylglutamate synthase (N-acetyl-L-cysteine)
  2. L-Cysteine:oxygen oxidoreductase
  3. 3-sulfino-L-alanine:2-oxoglutarate aminotransferase

  Catalysed by NAGS, CDO1, GOT1mitochondrial matrix, cytosolOne of 2 routes

• S-methyl glutathioneReach from here →
  1. glycine N-acyltransferase (N-arachidonoylglycine)
  2. gamma-L-glutamyl-L-cysteine + glycine + ATP = glutathione + ADP + phosphate + H(+)
  3. apo-[alkylcobalamin reductase] + methylcob(III)alamin + glutathione = S-methyl glutathione + cob(I)alamin-[alkylcobalamin reductase] + H(+)

  Catalysed by GLYAT, GLYATL2, GLYATL1, GSS and 1 moremitochondrial matrix

• 2-(9Z-octadecenoyl)-sn-glycero-3-phospho-(1'-sn-glycerol)Reach 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. 1-octadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phospho-(1'-sn-glycerol) + N-(acetyl)-sphing-4-enine = 2-(9Z-octadecenoyl)-sn-glycero-3-phospho-(1'-sn-glycerol) + 1-octadecanoyl-N-(acetyl)-sphing-4-enine

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

• beta-D-glucosyl-(1->3)-O-chenodeoxycholateReach from here →
  1. Propanoyl-CoA:acetyl-CoA C-acyltransferase
  2. chenodeoxycholoyl-CoA hydrolase
  3. a di-trans,poly-cis-dolichyl beta-D-glucosyl phosphate + chenodeoxycholate = beta-D-glucosyl-(1->3)-O-chenodeoxycholate + a di-trans,poly-cis-dolichyl phosphate + H(+)

  Catalysed by ACAA1, SCP2, MYO5B, ACOT7 and 3 moreperoxisomeOne of 2 routes

• N-octanoyl-(2S)-hydroxyglycineReach from here →
  1. Octanoyl-CoA:L-carnitine O-octanoyltransferase
  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 CROT, GLYATL2, PAMmitochondrial matrixOne of 2 routes

• N-decanoyl-(2S)-hydroxyglycineReach from here →
  1. medium-chain acyl-CoA ligase (decanoic acid)
  2. decanoyl-CoA + glycine = N-decanoylglycine + CoA + H(+)
  3. N-decanoylglycine + 2 L-ascorbate + O2 = N-decanoyl-(2S)-hydroxyglycine + 2 monodehydro-L-ascorbate radical + H2O

  Catalysed by ACSM4, ACSM1, ACSM2A, ACSM3 and 4 morecytosolOne of 2 routes

• N-dodecanoyl-(2S)-hydroxyglycineReach from here →
  1. long-chain-fatty-acid-CoA ligase (lauric acid)
  2. dodecanoyl-CoA + glycine = N-dodecanoylglycine + CoA + H(+)
  3. N-dodecanoylglycine + 2 L-ascorbate + O2 = N-dodecanoyl-(2S)-hydroxyglycine + 2 monodehydro-L-ascorbate radical + H2O

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 6 morecytosolOne of 2 routes

• N-tetradecanoyl-(2S)-hydroxyglycineReach from here →
  1. long-chain-fatty-acid-CoA ligase (myristic acid)
  2. tetradecanoyl-CoA + glycine = N-tetradecanoylglycine + CoA + H(+)
  3. N-tetradecanoylglycine + 2 L-ascorbate + O2 = N-tetradecanoyl-(2S)-hydroxyglycine + 2 monodehydro-L-ascorbate radical + H2O

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 6 morecytosolOne of 2 routes

• N-(9Z-octadecenoyl)-(2S)-hydroxyglycineReach from here →
  1. glycine N-acyltransferase (N-arachidonoylglycine)
  2. glycine + 2-oxoglutarate = glyoxylate + L-glutamate
  3. N-(9Z-octadecenoyl)-(2S)-hydroxyglycine = (9Z)-octadecenamide + glyoxylate

  Catalysed by GLYAT, GLYATL2, GLYATL1, AADAT and 1 moremitochondrial matrixOne of 2 routes

• N-(9Z,12Z,15Z)-octadecatrienoyl-(2S)-hydroxyglycineReach from here →
  1. glycine N-acyltransferase (N-arachidonoylglycine)
  2. glycine + 2-oxoglutarate = glyoxylate + L-glutamate
  3. N-(9Z,12Z,15Z)-octadecatrienoyl-(2S)-hydroxyglycine = (9Z,12Z,15Z)-octadecatrienamide + glyoxylate

  Catalysed by GLYAT, GLYATL2, GLYATL1, AADAT and 1 moremitochondrial matrix

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

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