(4Z,7Z,10Z,13Z,16Z)-docosapentaenoyl-CoA

Three steps

• an N-acylsphinganine-1-phosphoethanolamineReach from here →
  1. acyl-CoA pool formation and breakdown
  2. sphingosine N-acyltransferase (sphinganine)
  3. an N-acylsphinganine + a 1,2-diacyl-sn-glycero-3-phosphoethanolamine = an N-acylsphinganine-1-phosphoethanolamine + a 1,2-diacyl-sn-glycerol

  Catalysed by CERS1, CERS6, CERS3, CERS5 and 4 morecytosolOne of 2 routes

• N-hexadecanoyl-(4R)-hydroxysphinganine-1-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. N-hexadecanoyl-(4R)-hydroxysphinganine + a 1,2-diacyl-sn-glycero-3-phosphoethanolamine = N-hexadecanoyl-(4R)-hydroxysphinganine-1-phosphoethanolamine + a 1,2-diacyl-sn-glycerol

  Catalysed by LPCAT4, LPCAT3, MBOAT1, MBOAT2 and 2 morecytosol

• an N-acyl-(4R)-4-hydroxysphinganine-1-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. an N-acyl-(4R)-4-hydroxysphinganine + a 1,2-diacyl-sn-glycero-3-phosphoethanolamine = an N-acyl-(4R)-4-hydroxysphinganine-1-phosphoethanolamine + a 1,2-diacyl-sn-glycerol

  Catalysed by LPCAT4, LPCAT3, MBOAT1, MBOAT2 and 2 morecytosol

• tricosanoateReach from here →
  1. (4Z,7Z,10Z,13Z,16Z)-docosapentaenoyl-CoA hydrolase
  2. long-chain-fatty-acid-CoA ligase (tricosanoic acid)
  3. Tricosanoyl-CoA hydrolase

  Catalysed by BAAT, THEM4, SLC27A2, ACSL4 and 7 morecytosol

• thio-Mo-molybdopterinReach from here →
  1. (4Z,7Z,10Z,13Z,16Z)-docosapentaenoyl-CoA hydrolase
  2. N-acetylglutamate synthase (N-acetyl-L-cysteine)
  3. Mo-molybdopterin + L-cysteine + AH2 = thio-Mo-molybdopterin + L-alanine + A + H2O

  Catalysed by BAAT, THEM4, NAGS, MOCOScytosol, mitochondrial matrix

• cholesteryl octadecanoateReach from here →
  1. (4Z,7Z,10Z,13Z,16Z)-docosapentaenoyl-CoA hydrolase
  2. long-chain-fatty-acid-CoA ligase (stearate)
  3. Acyl-CoA:cholesterol O-acyltransferase

  Catalysed by BAAT, THEM4, SLC27A2, ACSL4 and 7 morecytosol, endoplasmic reticulumOne of 6 routes

• N-octadecanoylhexadecasphinganineReach from here →
  1. (4Z,7Z,10Z,13Z,16Z)-docosapentaenoyl-CoA hydrolase
  2. long-chain-fatty-acid-CoA ligase (stearate)
  3. hexadecasphinganine + octadecanoyl-CoA = N-octadecanoylhexadecasphinganine + CoA + H(+)

  Catalysed by BAAT, THEM4, SLC27A2, ACSL4 and 7 morecytosol

• 1-hexadecanoyl-2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-phosphateReach from here →
  1. (4Z,7Z,10Z,13Z,16Z)-docosapentaenoyl-CoA hydrolase
  2. long-chain-fatty-acid-CoA ligase (DHA)
  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 BAAT, THEM4, SLC27A2, ACSL4 and 7 morecytosol

• 1-hexadecanoyl-2-eicosanoyl-sn-glycero-3-phosphocholineReach from here →
  1. (4Z,7Z,10Z,13Z,16Z)-docosapentaenoyl-CoA hydrolase
  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 BAAT, THEM4, SLC27A2, ACSL4 and 7 morecytosol

• glycodeoxycholateReach from here →
  1. (4Z,7Z,10Z,13Z,16Z)-docosapentaenoyl-CoA hydrolase
  2. cholate-CoA ligase (3alpha,12alpha-dihydroxy-5beta-cholanate)
  3. deoxycholoyl-CoA to glycodeoxycholate conversion

  Catalysed by BAAT, THEM4, SLC27A2, SLC27A5cytosolOne of 3 routes

• sphinga-4E,14Z-dienineReach from here →
  1. (4Z,7Z,10Z,13Z,16Z)-docosapentaenoyl-CoA hydrolase
  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 BAAT, THEM4, ASAH1, ACER2 and 3 morecytosol, Golgi apparatus

• 1',3'-bis-[1,2-di-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phospho]-glycerolReach from here →
  1. (4Z,7Z,10Z,13Z,16Z)-docosapentaenoyl-CoA hydrolase
  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 BAAT, THEM4, SLC27A2, ACSL4 and 7 morecytosol

• a 1-acyl-2-octadecanoyl-sn-glycero-3-phospho-(1D-myo-inositol)Reach from here →
  1. (4Z,7Z,10Z,13Z,16Z)-docosapentaenoyl-CoA hydrolase
  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 BAAT, THEM4, SLC27A2, ACSL4 and 6 morecytosol

• cholesteryl (9Z)-hexadecenoateReach from here →
  1. (4Z,7Z,10Z,13Z,16Z)-docosapentaenoyl-CoA hydrolase
  2. long-chain-fatty-acid-CoA ligase (palmitolate)
  3. (9Z)-hexadecenoyl-CoA + cholesterol = cholesteryl (9Z)-hexadecenoate + CoA

  Catalysed by BAAT, THEM4, SLC27A2, ACSL4 and 7 morecytosol

• (9Z,12Z,15Z-octadecatrienoyl)-cholesterolReach from here →
  1. (4Z,7Z,10Z,13Z,16Z)-docosapentaenoyl-CoA hydrolase
  2. long-chain-fatty-acid-CoA ligase (linolenate)
  3. (9Z,12Z,15Z)-octadecatrienoyl-CoA + cholesterol = (9Z,12Z,15Z-octadecatrienoyl)-cholesterol + CoA

  Catalysed by BAAT, THEM4, SLC27A2, ACSL4 and 7 morecytosol

• cholesteryl (8Z,11Z,14Z)-eicosatrienoateReach from here →
  1. (4Z,7Z,10Z,13Z,16Z)-docosapentaenoyl-CoA hydrolase
  2. long-chain-fatty-acid-CoA ligase (dihomo-gamma-linolenate)
  3. Acyl-CoA:cholesterol O-acyltransferase

  Catalysed by BAAT, THEM4, SLC27A2, ACSL4 and 8 morecytosol, endoplasmic reticulumOne of 5 routes

• a monoacyl-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 monoacyl-sn-glycero-3-phosphocholine + a fatty acid + H(+)

  Catalysed by LPGAT1, PNLIPRP2cytosol

• 2-(acylamino)ethyl fatty acidReach 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. an N-acylethanolamine + a 1,2-diacyl-sn-glycero-3-phosphocholine = 2-(acylamino)ethyl fatty acid + a 2-acyl-sn-glycero-3-phosphocholine

  Catalysed by LPGAT1, PLA2G15cytosolOne of 2 routes

• 1-O-acyl-N-(acetyl)-sphing-4-enineReach 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. N-(acetyl)-sphing-4-enine + a 1,2-diacyl-sn-glycero-3-phosphocholine = 1-O-acyl-N-(acetyl)-sphing-4-enine + a 1-acyl-sn-glycero-3-phosphocholine

  Catalysed by LPGAT1, PLA2G15cytosolOne of 8 routes

• O-tetradecanoyl-(R)-carnitineReach from here →
  1. (4Z,7Z,10Z,13Z,16Z)-docosapentaenoyl-CoA hydrolase
  2. long-chain-fatty-acid-CoA ligase (myristic acid)
  3. tetradecanoyl-CoA + (R)-carnitine = O-tetradecanoyl-(R)-carnitine + CoA

  Catalysed by BAAT, THEM4, SLC27A2, ACSL4 and 7 morecytosol

• O-octadecanoyl-(R)-carnitineReach from here →
  1. (4Z,7Z,10Z,13Z,16Z)-docosapentaenoyl-CoA hydrolase
  2. long-chain-fatty-acid-CoA ligase (stearate)
  3. (R)-carnitine + octadecanoyl-CoA = O-octadecanoyl-(R)-carnitine + CoA

  Catalysed by BAAT, THEM4, SLC27A2, ACSL4 and 6 morecytosol

• O-eicosanoyl-(R)-carnitineReach from here →
  1. (4Z,7Z,10Z,13Z,16Z)-docosapentaenoyl-CoA hydrolase
  2. long-chain-fatty-acid-CoA ligase (eicosanoate)
  3. eicosanoyl-CoA + (R)-carnitine = O-eicosanoyl-(R)-carnitine + CoA

  Catalysed by BAAT, THEM4, SLC27A2, ACSL4 and 7 morecytosol

• O-4,8-dimethylnonanoyl-(R)-carnitineReach from here →
  1. (4Z,7Z,10Z,13Z,16Z)-docosapentaenoyl-CoA hydrolase
  2. Carnitine O-Palmitoyltransferase
  3. Carnitine Dimethyl Nonanoyl Transferase, Revsible, Peroxisomal

  Catalysed by BAAT, THEM4, CPT1A, CPT1C and 3 morecytosol, peroxisomeOne of 7 routes

• 1,2-diacyl-sn-glycero-3-phosphoethanolReach 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. ethanol + a 1,2-diacyl-sn-glycero-3-phosphocholine = 1,2-diacyl-sn-glycero-3-phosphoethanol + choline

  Catalysed by LPGAT1, PLD1cytosol

• 1-octadecanoyl-2-(9Z,12Z)-octadecadienoyl-sn-glycero-3-phosphocholineReach from here →
  1. (4Z,7Z,10Z,13Z,16Z)-docosapentaenoyl-CoA hydrolase
  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 BAAT, THEM4, SLC27A2, ACSL4 and 6 morecytosol

• 1-octadecanoyl-2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-phosphocholineReach from here →
  1. (4Z,7Z,10Z,13Z,16Z)-docosapentaenoyl-CoA hydrolase
  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 BAAT, THEM4, SLC27A2, ACSL4 and 6 morecytosol

• N-tetradecanoylglycineReach from here →
  1. (4Z,7Z,10Z,13Z,16Z)-docosapentaenoyl-CoA hydrolase
  2. long-chain-fatty-acid-CoA ligase (myristic acid)
  3. tetradecanoyl-CoA + glycine = N-tetradecanoylglycine + CoA + H(+)

  Catalysed by BAAT, THEM4, SLC27A2, ACSL4 and 7 morecytosolOne of 2 routes

• N-eicosanoylglycinateReach from here →
  1. (4Z,7Z,10Z,13Z,16Z)-docosapentaenoyl-CoA hydrolase
  2. long-chain-fatty-acid-CoA ligase (eicosanoate)
  3. eicosanoyl-CoA + glycine = N-eicosanoylglycinate + CoA + H(+)

  Catalysed by BAAT, THEM4, SLC27A2, ACSL4 and 6 morecytosolOne of 2 routes

• N-docosanoylglycineReach from here →
  1. (4Z,7Z,10Z,13Z,16Z)-docosapentaenoyl-CoA hydrolase
  2. long-chain-fatty-acid-CoA ligase (behenic acid)
  3. docosanoyl-CoA + glycine = N-docosanoylglycine + CoA + H(+)

  Catalysed by BAAT, THEM4, SLC27A2, ACSL4 and 6 morecytosolOne of 2 routes

• N-hexacosanoylglycineReach from here →
  1. (4Z,7Z,10Z,13Z,16Z)-docosapentaenoyl-CoA hydrolase
  2. long-chain-fatty-acid-CoA ligase (cerotic acid)
  3. hexacosanoyl-CoA + glycine = N-hexacosanoylglycine + CoA + H(+)

  Catalysed by BAAT, THEM4, SLC27A2, ACSL4 and 6 morecytosolOne of 2 routes

• (2E,5Z)-tetradecadienoyl-CoAReach from here →
  1. (4Z,7Z,10Z,13Z,16Z)-docosapentaenoyl-CoA hydrolase
  2. long-chain-fatty-acid-CoA ligase (physeteric acid)
  3. medium-chain acyl-CoA dehydrogenase (5-tetradecenoyl-CoA)

  Catalysed by BAAT, THEM4, SLC27A2, ACSL4 and 10 morecytosol, mitochondrial matrixOne of 4 routes

• (2E,7Z)-hexadecadienoyl-CoAReach from here →
  1. (4Z,7Z,10Z,13Z,16Z)-docosapentaenoyl-CoA hydrolase
  2. long-chain-fatty-acid-CoA ligase (7-palmitoleic acid)
  3. medium-chain acyl-CoA dehydrogenase (7-hexadecenoyl-CoA)

  Catalysed by BAAT, THEM4, SLC27A2, ACSL4 and 10 morecytosol, mitochondrial matrixOne of 4 routes

• cholesteryl (11Z)-octadecenoateReach from here →
  1. (4Z,7Z,10Z,13Z,16Z)-docosapentaenoyl-CoA hydrolase
  2. Transport of 11-Octadecenoyl Carnitine into the Mitochondrial Matrix
  3. (11Z)-octadecenoyl-CoA + cholesterol = cholesteryl (11Z)-octadecenoate + CoA

  Catalysed by BAAT, THEM4, CPT1A, CPT1C and 2 morecytosol

• (12S)-hydroperoxy-(5Z,8Z,10E,14Z,17Z)-eicosapentaenoateReach from here →
  1. Beta Oxidation of Long Chain Fatty Acid
  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 ACAA1, HSD17B4, EHHADH, ACOX1 and 4 moreperoxisome, cytosol

• (18R)-hydroxy-(5Z,8Z,11Z,14Z,16E)-eicosapentaenoateReach from here →
  1. Beta Oxidation of Long Chain Fatty Acid
  2. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA hydrolase
  3. prostaglandin-endoperoxide synthase (EPA)

  Catalysed by ACAA1, HSD17B4, EHHADH, ACOX1 and 5 moreperoxisome, cytosolOne of 2 routes

• (15R)-hydroxy-(5Z,8Z,11Z,13E,17Z)-eicosapentaenoateReach from here →
  1. Beta Oxidation of Long Chain Fatty Acid
  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 ACAA1, HSD17B4, EHHADH, ACOX1 and 4 moreperoxisome, cytosol

• (11R)-hydroxy-(5Z,8Z,12E,14Z,17Z)-eicosapentaenoateReach from here →
  1. Beta Oxidation of Long Chain Fatty Acid
  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 ACAA1, HSD17B4, EHHADH, ACOX1 and 4 moreperoxisome, cytosol

• taurochenodeoxycholateReach from here →
  1. (4Z,7Z,10Z,13Z,16Z)-docosapentaenoyl-CoA hydrolase
  2. Propanoyl-CoA:acetyl-CoA C-acyltransferase
  3. 3alpha,7alpha-dihydroxy-5beta-cholanoyl-CoA:taurine N-choloyltransferase

  Catalysed by BAAT, THEM4, ACAA1, SCP2 and 1 morecytosol, peroxisomeOne of 5 routes