CHEBI:16108

Three steps

• (7Z,10Z,13Z,16Z,19Z)-docosapentaenoateReach from here →
  1. glyceronephosphate O-acyltransferase (DHAP)
  2. long-chain-fatty-acid-CoA ligase (DPA)
  3. (7Z,10Z,13Z,16Z,19Z)-docosapentaenoyl-CoA hydrolase

  Catalysed by GNPAT, SLC27A2, ACSL4, ACSL3 and 7 moreperoxisome, cytosolOne of 13 routes

• (7Z,10Z,13Z,16Z)-docosatetraenoateReach from here →
  1. glyceronephosphate O-acyltransferase (DHAP)
  2. long-chain-fatty-acid-CoA ligase (adrenic acid)
  3. (7Z,10Z,13Z,16Z)-docosatetraenoyl-CoA hydrolase

  Catalysed by GNPAT, SLC27A2, ACSL4, ACSL3 and 7 moreperoxisome, cytosolOne of 14 routes

• 2,6,10,14-tetramethylpentadecanoateReach from here →
  1. glyceronephosphate O-acyltransferase (DHAP)
  2. fatty-acid-CoA ligase
  3. peroxisomal acyl-CoA thioesterase

  Catalysed by GNPAT, SLC27A2, ACOT2peroxisome, cytosolOne of 2 routes

• a 1,3-diacyl-sn-glycerolReach from here →
  1. glyceronephosphate O-acyltransferase (DHAP)
  2. acyl-CoA:sphingosine N-acyltransferase
  3. a 3-acyl-sn-glycerol + an acyl-CoA = a 1,3-diacyl-sn-glycerol + CoA

  Catalysed by GNPAT, ASAH1, ACER2, ACER1 and 2 moreperoxisome, Golgi apparatusOne of 2 routes

• a 1-O-(1Z-alkenyl)-2-acyl-sn-glycero-3-phosphocholineReach from here →
  1. glyceronephosphate O-acyltransferase (DHAP)
  2. acyl-CoA:sphingosine N-acyltransferase
  3. a 1-O-(1Z-alkenyl)-sn-glycero-3-phosphocholine + an acyl-CoA = a 1-O-(1Z-alkenyl)-2-acyl-sn-glycero-3-phosphocholine + CoA

  Catalysed by GNPAT, ASAH1, ACER2, ACER1 and 3 moreperoxisome, Golgi apparatus

• a 1-O-(1Z-alkenyl)-2-acyl-sn-glycero-3-phosphoethanolamineReach from here →
  1. glyceronephosphate O-acyltransferase (DHAP)
  2. acyl-CoA:sphingosine N-acyltransferase
  3. a 1-O-(1Z-alkenyl)-sn-glycero-3-phosphoethanolamine + an acyl-CoA = a 1-O-(1Z-alkenyl)-2-acyl-sn-glycero-3-phosphoethanolamine + CoA

  Catalysed by GNPAT, ASAH1, ACER2, ACER1 and 2 moreperoxisome, Golgi apparatus

• 1-O-(1Z)-alkenyl-2-octanoyl-sn-glycero-3-phosphoethanolamineReach from here →
  1. glyceronephosphate O-acyltransferase (DHAP)
  2. Octanoyl-CoA:L-carnitine O-octanoyltransferase
  3. a 1-O-(1Z-alkenyl)-sn-glycero-3-phosphoethanolamine + octanoyl-CoA = 1-O-(1Z)-alkenyl-2-octanoyl-sn-glycero-3-phosphoethanolamine + CoA

  Catalysed by GNPAT, CROT, LPCAT4peroxisome, mitochondrial matrix

• 1-O-(1Z)-alkenyl-2-octadecanoyl-sn-glycero-3-phosphoethanolamineReach from here →
  1. glyceronephosphate O-acyltransferase (DHAP)
  2. long-chain-fatty-acid-CoA ligase (stearate)
  3. a 1-O-(1Z-alkenyl)-sn-glycero-3-phosphoethanolamine + octadecanoyl-CoA = 1-O-(1Z)-alkenyl-2-octadecanoyl-sn-glycero-3-phosphoethanolamine + CoA

  Catalysed by GNPAT, SLC27A2, ACSL4, ACSL3 and 5 moreperoxisome, cytosol

• tetracosan-1-olReach from here →
  1. glyceronephosphate O-acyltransferase (DHAP)
  2. long-chain-fatty-acid-CoA ligase (lignocerate)
  3. tetracosanoyl-CoA + 2 NADPH + 2 H(+) = tetracosan-1-ol + 2 NADP(+) + CoA

  Catalysed by GNPAT, SLC27A2, ACSL4, ACSL3 and 6 moreperoxisome, cytosol

• (2E,9Z)-hexadecadienoyl-CoAReach from here →
  1. glyceronephosphate O-acyltransferase (DHAP)
  2. long-chain-fatty-acid-CoA ligase (palmitolate)
  3. medium-chain acyl-CoA dehydrogenase (palmitoleoyl-CoA)

  Catalysed by GNPAT, SLC27A2, ACSL4, ACSL3 and 9 moreperoxisome, cytosol, mitochondrial matrixOne of 3 routes

• trans-2-heptadecenoyl-CoAReach from here →
  1. glyceronephosphate O-acyltransferase (DHAP)
  2. long-chain-fatty-acid-CoA ligase (margaric acid)
  3. medium-chain acyl-CoA dehydrogenase (heptadecanoyl-CoA)

  Catalysed by GNPAT, SLC27A2, ACSL4, ACSL3 and 9 moreperoxisome, cytosol, mitochondrial matrixOne of 2 routes

• (2E,9Z)-octadecadienoyl-CoAReach from here →
  1. glyceronephosphate O-acyltransferase (DHAP)
  2. Transport of octadecenoyl-CoA into Mitochondrial Matrix
  3. medium-chain acyl-CoA dehydrogenase (oleoyl-CoA)

  Catalysed by GNPAT, CPT1A, CPT1C, CPT1B and 4 moreperoxisome, cytosol, mitochondrial matrixOne of 2 routes

• (2E,9Z,12Z)-octadecatrienoyl-CoAReach from here →
  1. glyceronephosphate O-acyltransferase (DHAP)
  2. long-chain-fatty-acid-CoA ligase ((6Z,9Z)-octadecadienoic acid)
  3. (9Z,12Z)-octadecadienoyl-CoA + oxidized [electron-transfer flavoprotein] + H(+) = (2E,9Z,12Z)-octadecatrienoyl-CoA + reduced [electron-transfer flavoprotein]

  Catalysed by GNPAT, SLC27A2, ACSL4, ACSL3 and 8 moreperoxisome, cytosol

• (2E,4Z,7Z,10Z,13Z,16Z,19Z)-docosaheptaenoyl-CoAReach from here →
  1. glyceronephosphate O-acyltransferase (DHAP)
  2. long-chain-fatty-acid-CoA ligase (DHA)
  3. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoyl-CoA + O2 = (2E,4Z,7Z,10Z,13Z,16Z,19Z)-docosaheptaenoyl-CoA + H2O2

  Catalysed by GNPAT, SLC27A2, ACSL4, ACSL3 and 6 moreperoxisome, cytosol

• N-(9Z-octadecenoyl)-sphing-4-enineReach from here →
  1. glyceronephosphate O-acyltransferase (DHAP)
  2. acyl-CoA:sphingosine N-acyltransferase
  3. N-(9Z-octadecenoyl)-sphing-4-enine + H2O = sphing-4-enine + (9Z)-octadecenoate

  Catalysed by GNPAT, ASAH1, ACER2, ACER1 and 2 moreperoxisome, Golgi apparatus

• (5Z,8Z,11Z)-eicosatrienoateReach from here →
  1. Acyl-CoA:glycerone-phosphate O-acyltransferase
  2. alkylglycerone phosphate synthase (acylglycerone-phosphate)
  3. (10Z)-heptadecenoic acid formation

  Catalysed by GNPAT, AGPScytosol, peroxisome, extracellular spaceOne of 12 routes

• 9-cis-retinolReach from here →
  1. glyceronephosphate O-acyltransferase (DHAP)
  2. Palmitoyl-CoA:retinol O-acyltransferase
  3. 11-cis-retinol = 9-cis-retinol

  Catalysed by GNPAT, DGAT1, LRAT, AWAT1 and 3 moreperoxisome, cytosol

• tricosanoateReach from here →
  1. glyceronephosphate O-acyltransferase (DHAP)
  2. long-chain-fatty-acid-CoA ligase (tricosanoic acid)
  3. Tricosanoyl-CoA hydrolase

  Catalysed by GNPAT, SLC27A2, ACSL4, ACSL3 and 7 moreperoxisome, cytosolOne of 13 routes

• thio-Mo-molybdopterinReach from here →
  1. glyceronephosphate O-acyltransferase (DHAP)
  2. N-acetylglutamate synthase (N-acetyl-L-cysteine)
  3. Mo-molybdopterin + L-cysteine + AH2 = thio-Mo-molybdopterin + L-alanine + A + H2O

  Catalysed by GNPAT, NAGS, MOCOSperoxisome, mitochondrial matrix

• cholesteryl octadecanoateReach from here →
  1. glyceronephosphate O-acyltransferase (DHAP)
  2. long-chain-fatty-acid-CoA ligase (stearate)
  3. Acyl-CoA:cholesterol O-acyltransferase

  Catalysed by GNPAT, SLC27A2, ACSL4, ACSL3 and 6 moreperoxisome, cytosol, endoplasmic reticulumOne of 2 routes

• N-octadecanoylhexadecasphinganineReach from here →
  1. glyceronephosphate O-acyltransferase (DHAP)
  2. long-chain-fatty-acid-CoA ligase (stearate)
  3. hexadecasphinganine + octadecanoyl-CoA = N-octadecanoylhexadecasphinganine + CoA + H(+)

  Catalysed by GNPAT, SLC27A2, ACSL4, ACSL3 and 6 moreperoxisome, cytosol

• 1-hexadecanoyl-2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-phosphateReach from here →
  1. sn-Glycerol-3-phosphate:NAD+ 2-oxidoreductase
  2. glycerol-3-phosphate 1-O-acyltransferase (palmitoyl-CoA)
  3. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoyl-CoA + 1-hexadecanoyl-sn-glycero-3-phosphate = 1-hexadecanoyl-2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-phosphate + CoA

  Catalysed by GPD1, GPD1L, GPAT3, GPAT2 and 3 morecytosolOne of 2 routes

• 1-hexadecanoyl-2-eicosanoyl-sn-glycero-3-phosphocholineReach from here →
  1. glyceronephosphate O-acyltransferase (DHAP)
  2. long-chain-fatty-acid-CoA ligase (eicosanoate)
  3. eicosanoyl-CoA + 1-hexadecanoyl-sn-glycero-3-phosphocholine = 1-hexadecanoyl-2-eicosanoyl-sn-glycero-3-phosphocholine + CoA

  Catalysed by GNPAT, SLC27A2, ACSL4, ACSL3 and 6 moreperoxisome, cytosol

• glycodeoxycholateReach from here →
  1. glyceronephosphate O-acyltransferase (DHAP)
  2. cholate-CoA ligase (3alpha,12alpha-dihydroxy-5beta-cholanate)
  3. deoxycholoyl-CoA to glycodeoxycholate conversion

  Catalysed by GNPAT, SLC27A2, SLC27A5peroxisome, cytosolOne of 3 routes

• sphinga-4E,14Z-dienineReach from here →
  1. glyceronephosphate O-acyltransferase (DHAP)
  2. acyl-CoA:sphingosine N-acyltransferase
  3. sphing-4-enine + 2 Fe(II)-[cytochrome b5] + O2 + 2 H(+) = sphinga-4E,14Z-dienine + 2 Fe(III)-[cytochrome b5] + 2 H2O

  Catalysed by GNPAT, ASAH1, ACER2, ACER1 and 2 moreperoxisome, Golgi apparatus

• 1',3'-bis-[1,2-di-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phospho]-glycerolReach from here →
  1. glyceronephosphate O-acyltransferase (DHAP)
  2. long-chain-fatty-acid-CoA ligase ((6Z,9Z)-octadecadienoic acid)
  3. 1'-[1,2-di-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phospho]-3'-[1-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phospho]-glycerol + (9Z,12Z)-octadecadienoyl-CoA = 1',3'-bis-[1,2-di-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phospho]-glycerol + CoA

  Catalysed by GNPAT, SLC27A2, ACSL4, ACSL3 and 6 moreperoxisome, cytosol

• a 1-acyl-2-octadecanoyl-sn-glycero-3-phospho-(1D-myo-inositol)Reach from here →
  1. glyceronephosphate O-acyltransferase (DHAP)
  2. long-chain-fatty-acid-CoA ligase (stearate)
  3. a 1-acyl-sn-glycero-3-phospho-(1D-myo-inositol) + octadecanoyl-CoA = a 1-acyl-2-octadecanoyl-sn-glycero-3-phospho-(1D-myo-inositol) + CoA

  Catalysed by GNPAT, SLC27A2, ACSL4, ACSL3 and 5 moreperoxisome, cytosol

• cholesteryl (9Z)-hexadecenoateReach from here →
  1. glyceronephosphate O-acyltransferase (DHAP)
  2. long-chain-fatty-acid-CoA ligase (palmitolate)
  3. (9Z)-hexadecenoyl-CoA + cholesterol = cholesteryl (9Z)-hexadecenoate + CoA

  Catalysed by GNPAT, SLC27A2, ACSL4, ACSL3 and 6 moreperoxisome, cytosol

• (9Z,12Z,15Z-octadecatrienoyl)-cholesterolReach from here →
  1. glyceronephosphate O-acyltransferase (DHAP)
  2. long-chain-fatty-acid-CoA ligase (linolenate)
  3. (9Z,12Z,15Z)-octadecatrienoyl-CoA + cholesterol = (9Z,12Z,15Z-octadecatrienoyl)-cholesterol + CoA

  Catalysed by GNPAT, SLC27A2, ACSL4, ACSL3 and 6 moreperoxisome, cytosol

• cholesteryl (8Z,11Z,14Z)-eicosatrienoateReach from here →
  1. glyceronephosphate O-acyltransferase (DHAP)
  2. long-chain-fatty-acid-CoA ligase (dihomo-gamma-linolenate)
  3. Acyl-CoA:cholesterol O-acyltransferase

  Catalysed by GNPAT, SLC27A2, ACSL4, ACSL3 and 7 moreperoxisome, cytosol, endoplasmic reticulum

• O-tetradecanoyl-(R)-carnitineReach from here →
  1. glyceronephosphate O-acyltransferase (DHAP)
  2. long-chain-fatty-acid-CoA ligase (myristic acid)
  3. tetradecanoyl-CoA + (R)-carnitine = O-tetradecanoyl-(R)-carnitine + CoA

  Catalysed by GNPAT, SLC27A2, ACSL4, ACSL3 and 6 moreperoxisome, cytosol

• O-octadecanoyl-(R)-carnitineReach from here →
  1. glyceronephosphate O-acyltransferase (DHAP)
  2. long-chain-fatty-acid-CoA ligase (stearate)
  3. (R)-carnitine + octadecanoyl-CoA = O-octadecanoyl-(R)-carnitine + CoA

  Catalysed by GNPAT, SLC27A2, ACSL4, ACSL3 and 5 moreperoxisome, cytosol

• O-eicosanoyl-(R)-carnitineReach from here →
  1. glyceronephosphate O-acyltransferase (DHAP)
  2. long-chain-fatty-acid-CoA ligase (eicosanoate)
  3. eicosanoyl-CoA + (R)-carnitine = O-eicosanoyl-(R)-carnitine + CoA

  Catalysed by GNPAT, SLC27A2, ACSL4, ACSL3 and 6 moreperoxisome, cytosol

• O-4,8-dimethylnonanoyl-(R)-carnitineReach from here →
  1. glyceronephosphate O-acyltransferase (DHAP)
  2. Carnitine O-Palmitoyltransferase
  3. Carnitine Dimethyl Nonanoyl Transferase, Revsible, Peroxisomal

  Catalysed by GNPAT, CPT1A, CPT1C, CPT1B and 2 moreperoxisome, cytosolOne of 7 routes

• 1-octadecanoyl-2-(9Z,12Z)-octadecadienoyl-sn-glycero-3-phosphocholineReach from here →
  1. glyceronephosphate O-acyltransferase (DHAP)
  2. long-chain-fatty-acid-CoA ligase (stearate)
  3. 2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphocholine + octadecanoyl-CoA = 1-octadecanoyl-2-(9Z,12Z)-octadecadienoyl-sn-glycero-3-phosphocholine + CoA

  Catalysed by GNPAT, SLC27A2, ACSL4, ACSL3 and 5 moreperoxisome, cytosol

• 1-octadecanoyl-2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-phosphocholineReach from here →
  1. glyceronephosphate O-acyltransferase (DHAP)
  2. long-chain-fatty-acid-CoA ligase (stearate)
  3. 2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-phosphocholine + octadecanoyl-CoA = 1-octadecanoyl-2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-phosphocholine + CoA

  Catalysed by GNPAT, SLC27A2, ACSL4, ACSL3 and 5 moreperoxisome, cytosol

• (5Z,8Z,11Z,14Z,17Z-eicosapentaenoyl)-cholesterolReach from here →
  1. glyceronephosphate O-acyltransferase (DHAP)
  2. long-chain-fatty-acid-CoA ligase (EPA)
  3. Acyl-CoA:cholesterol O-acyltransferase

  Catalysed by GNPAT, SLC27A2, ACSL4, ACSL3 and 7 moreperoxisome, cytosol, endoplasmic reticulumOne of 2 routes

• N-tetradecanoylglycineReach from here →
  1. glyceronephosphate O-acyltransferase (DHAP)
  2. long-chain-fatty-acid-CoA ligase (myristic acid)
  3. tetradecanoyl-CoA + glycine = N-tetradecanoylglycine + CoA + H(+)

  Catalysed by GNPAT, SLC27A2, ACSL4, ACSL3 and 6 moreperoxisome, cytosolOne of 2 routes

• N-eicosanoylglycinateReach from here →
  1. glyceronephosphate O-acyltransferase (DHAP)
  2. long-chain-fatty-acid-CoA ligase (eicosanoate)
  3. eicosanoyl-CoA + glycine = N-eicosanoylglycinate + CoA + H(+)

  Catalysed by GNPAT, SLC27A2, ACSL4, ACSL3 and 6 moreperoxisome, cytosolOne of 2 routes

• N-docosanoylglycineReach from here →
  1. glyceronephosphate O-acyltransferase (DHAP)
  2. long-chain-fatty-acid-CoA ligase (behenic acid)
  3. docosanoyl-CoA + glycine = N-docosanoylglycine + CoA + H(+)

  Catalysed by GNPAT, SLC27A2, ACSL4, ACSL3 and 6 moreperoxisome, cytosolOne of 2 routes

• N-hexacosanoylglycineReach from here →
  1. glyceronephosphate O-acyltransferase (DHAP)
  2. long-chain-fatty-acid-CoA ligase (cerotic acid)
  3. hexacosanoyl-CoA + glycine = N-hexacosanoylglycine + CoA + H(+)

  Catalysed by GNPAT, SLC27A2, ACSL4, ACSL3 and 6 moreperoxisome, cytosolOne of 2 routes

• an N(2)-acyl-L-glutamineReach from here →
  1. glyceronephosphate O-acyltransferase (DHAP)
  2. acyl-CoA:sphingosine N-acyltransferase
  3. an acyl-CoA + L-glutamine = an N(2)-acyl-L-glutamine + CoA + H(+)

  Catalysed by GNPAT, ASAH1, ACER2, ACER1 and 3 moreperoxisome, Golgi apparatus

• (2E,5Z)-tetradecadienoyl-CoAReach from here →
  1. glyceronephosphate O-acyltransferase (DHAP)
  2. long-chain-fatty-acid-CoA ligase (physeteric acid)
  3. medium-chain acyl-CoA dehydrogenase (5-tetradecenoyl-CoA)

  Catalysed by GNPAT, SLC27A2, ACSL4, ACSL3 and 9 moreperoxisome, cytosol, mitochondrial matrixOne of 4 routes

• (2E,7Z)-hexadecadienoyl-CoAReach from here →
  1. glyceronephosphate O-acyltransferase (DHAP)
  2. long-chain-fatty-acid-CoA ligase (7-palmitoleic acid)
  3. medium-chain acyl-CoA dehydrogenase (7-hexadecenoyl-CoA)

  Catalysed by GNPAT, SLC27A2, ACSL4, ACSL3 and 9 moreperoxisome, cytosol, mitochondrial matrixOne of 4 routes

• cholesteryl (11Z)-octadecenoateReach from here →
  1. glyceronephosphate O-acyltransferase (DHAP)
  2. Transport of 11-Octadecenoyl Carnitine into the Mitochondrial Matrix
  3. (11Z)-octadecenoyl-CoA + cholesterol = cholesteryl (11Z)-octadecenoate + CoA

  Catalysed by GNPAT, CPT1A, CPT1C, CPT1B and 1 moreperoxisome, cytosol

• a 3-oxoacyl-CoAReach from here →
  1. glyceronephosphate O-acyltransferase (DHAP)
  2. acyl-CoA:sphingosine N-acyltransferase
  3. an acyl-CoA + acetyl-CoA = a 3-oxoacyl-CoA + CoA

  Catalysed by GNPAT, ASAH1, ACER2, ACER1 and 5 moreperoxisome, Golgi apparatus

• taurochenodeoxycholateReach from here →
  1. glyceronephosphate O-acyltransferase (DHAP)
  2. Propanoyl-CoA:acetyl-CoA C-acyltransferase
  3. 3alpha,7alpha-dihydroxy-5beta-cholanoyl-CoA:taurine N-choloyltransferase

  Catalysed by GNPAT, ACAA1, SCP2, MYO5B and 1 moreperoxisomeOne of 5 routes

• 2-(1-hydroxyethyl)thiamine diphosphateReach from here →
  1. glycerone-phosphate phosphate-lyase (methylglyoxal-forming)
  2. 2-Oxopropanal:NADP+ oxidoreductase
  3. pyruvate:thiamin diphosphate acetaldehydetransferase (decarboxylating)

  Catalysed by PDHA1, PDHB, PDHA2cytosol, mitochondrial matrix