(11Z)-eicosenoyl-CoA

Three steps

• a 2-acyl-sn-glycero-3-phospho-L-serineReach from here →
  1. acyl-CoA pool formation and breakdown
  2. a 1-acyl-sn-glycero-3-phospho-L-serine + an acyl-CoA = a 1,2-diacyl-sn-glycero-3-phospho-L-serine + CoA
  3. a 1,2-diacyl-sn-glycero-3-phospho-L-serine + H2O = a 2-acyl-sn-glycero-3-phospho-L-serine + a fatty acid + H(+)

  Catalysed by LPCAT4, LPCAT3, MBOAT1, PLA1A and 2 morecytosolOne of 2 routes

• N-docosanoylsphinganineReach from here →
  1. (11Z)-eicosenoyl-CoA hydrolase
  2. long-chain-fatty-acid-CoA ligase (behenic acid)
  3. docosanoyl-CoA + sphinganine = N-docosanoylsphinganine + CoA + H(+)

  Catalysed by BAAT, ACOT6, ACOT1, SLC27A2 and 10 morecytosol

• N-eicosanoylsphinganineReach from here →
  1. (11Z)-eicosenoyl-CoA hydrolase
  2. long-chain-fatty-acid-CoA ligase (eicosanoate)
  3. eicosanoyl-CoA + sphinganine = N-eicosanoylsphinganine + CoA + H(+)

  Catalysed by BAAT, ACOT6, ACOT1, SLC27A2 and 10 morecytosol

• N-(octadecanoyl)-sphinganineReach from here →
  1. (11Z)-eicosenoyl-CoA hydrolase
  2. long-chain-fatty-acid-CoA ligase (stearate)
  3. sphinganine + octadecanoyl-CoA = N-(octadecanoyl)-sphinganine + CoA + H(+)

  Catalysed by BAAT, ACOT6, ACOT1, SLC27A2 and 12 morecytosol

• N-hexadecanoylsphinganineReach from here →
  1. acyl-CoA pool formation and breakdown
  2. a 2-acylglycerol + an acyl-CoA = a 1,2-diacyl-sn-glycerol + CoA
  3. N-hexadecanoylsphinganine + a 1,2-diacyl-sn-glycero-3-phosphocholine = N-hexadecanoyl-sphinganine-1-phosphocholine + a 1,2-diacyl-sn-glycerol

  Catalysed by MOGAT2, AWAT2, MOGAT1, SGMS1 and 1 morecytosol

• N-(tetradecanoyl)-sphinganineReach from here →
  1. (11Z)-eicosenoyl-CoA hydrolase
  2. long-chain-fatty-acid-CoA ligase (myristic acid)
  3. sphinganine + tetradecanoyl-CoA = N-(tetradecanoyl)-sphinganine + CoA + H(+)

  Catalysed by BAAT, ACOT6, ACOT1, SLC27A2 and 9 morecytosol

• an N-acylsphinganine-1-phosphocholineReach 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-phosphocholine = an N-acylsphinganine-1-phosphocholine + a 1,2-diacyl-sn-glycerol

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

• 3-oxohexadecasphinganineReach from here →
  1. (11Z)-eicosenoyl-CoA hydrolase
  2. long-chain-fatty-acid-CoA ligase (myristic acid)
  3. tetradecanoyl-CoA + L-serine + H(+) = 3-oxohexadecasphinganine + CO2 + CoA

  Catalysed by BAAT, ACOT6, ACOT1, SLC27A2 and 9 morecytosol

• 3-oxotetradecasphinganineReach from here →
  1. (11Z)-eicosenoyl-CoA hydrolase
  2. long-chain-fatty-acid-CoA ligase (lauric acid)
  3. dodecanoyl-CoA + L-serine + H(+) = 3-oxotetradecasphinganine + CO2 + CoA

  Catalysed by BAAT, ACOT6, ACOT1, SLC27A2 and 9 morecytosol

• Mo-molybdopterinReach from here →
  1. (11Z)-eicosenoyl-CoA hydrolase
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. Mo-molybdopterin + L-cysteine + AH2 = thio-Mo-molybdopterin + L-alanine + A + H2O

  Catalysed by BAAT, ACOT6, ACOT1, MOCOScytosol, mitochondrial matrix

• 3-oxooctadecanoyl-CoAReach from here →
  1. (11Z)-eicosenoyl-CoA hydrolase
  2. Palmitate:CoA ligase (AMP-forming)
  3. very-long-chain 3-oxoacyl-CoA synthase (malonyl-CoA)

  Catalysed by BAAT, ACOT6, ACOT1, SLC27A2 and 14 morecytosolOne of 2 routes

• 3-oxodocosanoyl-CoAReach from here →
  1. (11Z)-eicosenoyl-CoA hydrolase
  2. long-chain-fatty-acid-CoA ligase (eicosanoate)
  3. very-long-chain 3-oxoacyl-CoA synthase (eicosanoyl-CoA)

  Catalysed by BAAT, ACOT6, ACOT1, SLC27A2 and 14 morecytosolOne of 3 routes

• 3-oxo-(8Z,11Z,14Z)-eicosatrienoyl-CoAReach from here →
  1. (11Z)-eicosenoyl-CoA hydrolase
  2. long-chain-fatty-acid-CoA ligase (gamma-linolenate)
  3. (6Z,9Z,12Z)-octadecatrienoyl-CoA + malonyl-CoA + H(+) = 3-oxo-(8Z,11Z,14Z)-eicosatrienoyl-CoA + CO2 + CoA

  Catalysed by BAAT, ACOT6, ACOT1, SLC27A2 and 9 morecytosol

• 3-oxo-(8Z,11Z,14Z,17Z)-eicosatetraenoyl-CoAReach from here →
  1. (11Z)-eicosenoyl-CoA hydrolase
  2. long-chain-fatty-acid-CoA ligase (stearidonic acid)
  3. (6Z,9Z,12Z,15Z)-octadecatetraenoyl-CoA + malonyl-CoA + H(+) = 3-oxo-(8Z,11Z,14Z,17Z)-eicosatetraenoyl-CoA + CO2 + CoA

  Catalysed by BAAT, ACOT6, ACOT1, SLC27A2 and 8 morecytosol

• (8Z,11Z,14Z)-eicosatrienoateReach from here →
  1. (11Z)-eicosenoyl-CoA hydrolase
  2. (10Z)-heptadecenoic acid formation
  3. (10Z)-heptadecenoic acid formation

  Catalysed by BAAT, ACOT6, ACOT1cytosol, extracellular spaceOne of 14 routes

• 1-dodecanoyl-sn-glycerol 3-phosphateReach from here →
  1. (11Z)-eicosenoyl-CoA hydrolase
  2. long-chain-fatty-acid-CoA ligase (lauric acid)
  3. glycerol-3-phosphate 1-O-acyltransferase (lauroyl-CoA)

  Catalysed by BAAT, ACOT6, ACOT1, SLC27A2 and 11 morecytosolOne of 3 routes

• 1-tetradecanoyl-sn-glycerol 3-phosphateReach from here →
  1. (11Z)-eicosenoyl-CoA hydrolase
  2. long-chain-fatty-acid-CoA ligase (myristic acid)
  3. glycerol-3-phosphate 1-O-acyltransferase (myristoyl-CoA)

  Catalysed by BAAT, ACOT6, ACOT1, SLC27A2 and 11 morecytosolOne of 2 routes

• 1-hexadecanoyl-2-octadecanoyl-sn-glycero-3-phospho-(1D-myo-inositol)Reach from here →
  1. (11Z)-eicosenoyl-CoA hydrolase
  2. long-chain-fatty-acid-CoA ligase (stearate)
  3. 1-hexadecanoyl-sn-glycero-3-phospho-(1D-myo-inositol) + octadecanoyl-CoA = 1-hexadecanoyl-2-octadecanoyl-sn-glycero-3-phospho-(1D-myo-inositol) + CoA

  Catalysed by BAAT, ACOT6, ACOT1, SLC27A2 and 7 morecytosol

• 1-hexadecanoyl-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phospho-(1D-myo-inositol)Reach from here →
  1. (11Z)-eicosenoyl-CoA hydrolase
  2. long-chain-fatty-acid-CoA ligase ((6Z,9Z)-octadecadienoic acid)
  3. 1-hexadecanoyl-sn-glycero-3-phospho-(1D-myo-inositol) + (9Z,12Z)-octadecadienoyl-CoA = 1-hexadecanoyl-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phospho-(1D-myo-inositol) + CoA

  Catalysed by BAAT, ACOT6, ACOT1, SLC27A2 and 8 morecytosol

• 1-hexadecanoyl-2-octadecanoyl-sn-glycero-3-phospho-(1'-sn-glycerol)Reach from here →
  1. (11Z)-eicosenoyl-CoA hydrolase
  2. long-chain-fatty-acid-CoA ligase (stearate)
  3. 1-hexadecanoyl-sn-glycero-3-phospho-(1'-sn-glycerol) + octadecanoyl-CoA = 1-hexadecanoyl-2-octadecanoyl-sn-glycero-3-phospho-(1'-sn-glycerol) + CoA

  Catalysed by BAAT, ACOT6, ACOT1, SLC27A2 and 8 morecytosol

• 1-hexadecanoyl-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phospho-(1'-sn-glycerol)Reach from here →
  1. (11Z)-eicosenoyl-CoA hydrolase
  2. long-chain-fatty-acid-CoA ligase ((6Z,9Z)-octadecadienoic acid)
  3. 1-hexadecanoyl-sn-glycero-3-phospho-(1'-sn-glycerol) + (9Z,12Z)-octadecadienoyl-CoA = 1-hexadecanoyl-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phospho-(1'-sn-glycerol) + CoA

  Catalysed by BAAT, ACOT6, ACOT1, SLC27A2 and 8 morecytosol

• 1-hexadecanoyl-2-octadecanoyl-sn-glycero-3-phosphateReach from here →
  1. (11Z)-eicosenoyl-CoA hydrolase
  2. long-chain-fatty-acid-CoA ligase (stearate)
  3. 1-hexadecanoyl-sn-glycero-3-phosphate + octadecanoyl-CoA = 1-hexadecanoyl-2-octadecanoyl-sn-glycero-3-phosphate + CoA

  Catalysed by BAAT, ACOT6, ACOT1, SLC27A2 and 7 morecytosol

• 1-hexadecanoyl-2-tetradecanoyl-sn-glycero-3-phosphateReach from here →
  1. (11Z)-eicosenoyl-CoA hydrolase
  2. long-chain-fatty-acid-CoA ligase (myristic acid)
  3. 1-hexadecanoyl-sn-glycero-3-phosphate + tetradecanoyl-CoA = 1-hexadecanoyl-2-tetradecanoyl-sn-glycero-3-phosphate + CoA

  Catalysed by BAAT, ACOT6, ACOT1, SLC27A2 and 8 morecytosol

• N-dodecanoylsphing-4-enineReach from here →
  1. (11Z)-eicosenoyl-CoA hydrolase
  2. acyl-CoA:sphingosine N-acyltransferase
  3. N-dodecanoylsphing-4-enine + H2O = dodecanoate + sphing-4-enine

  Catalysed by BAAT, ACOT6, ACOT1, ASAH1 and 4 morecytosol, Golgi apparatus

• N-tetradecanoylsphing-4-enineReach from here →
  1. (11Z)-eicosenoyl-CoA hydrolase
  2. acyl-CoA:sphingosine N-acyltransferase
  3. N-tetradecanoylsphing-4-enine + H2O = sphing-4-enine + tetradecanoate

  Catalysed by BAAT, ACOT6, ACOT1, ASAH1 and 3 morecytosol, Golgi apparatus

• N-hexadecanoylsphing-4-enineReach from here →
  1. (11Z)-eicosenoyl-CoA hydrolase
  2. acyl-CoA:sphingosine N-acyltransferase
  3. sphing-4-enine + hexadecanoyl-CoA = N-hexadecanoylsphing-4-enine + CoA + H(+)

  Catalysed by BAAT, ACOT6, ACOT1, ASAH1 and 7 morecytosol, Golgi apparatusOne of 2 routes

• N-octadecanoylsphing-4-enineReach from here →
  1. (11Z)-eicosenoyl-CoA hydrolase
  2. long-chain-fatty-acid-CoA ligase (stearate)
  3. sphing-4-enine + octadecanoyl-CoA = N-octadecanoylsphing-4-enine + CoA + H(+)

  Catalysed by BAAT, ACOT6, ACOT1, SLC27A2 and 10 morecytosolOne of 3 routes

• N-eicosanoyl-sphing-4-enineReach from here →
  1. (11Z)-eicosenoyl-CoA hydrolase
  2. long-chain-fatty-acid-CoA ligase (eicosanoate)
  3. eicosanoyl-CoA + sphing-4-enine = N-eicosanoyl-sphing-4-enine + CoA + H(+)

  Catalysed by BAAT, ACOT6, ACOT1, SLC27A2 and 9 morecytosolOne of 2 routes

• N-tetracosanoyl-sphing-4-enineReach from here →
  1. (11Z)-eicosenoyl-CoA hydrolase
  2. long-chain-fatty-acid-CoA ligase (lignocerate)
  3. tetracosanoyl-CoA + sphing-4-enine = N-tetracosanoyl-sphing-4-enine + CoA + H(+)

  Catalysed by BAAT, ACOT6, ACOT1, SLC27A2 and 8 morecytosolOne of 2 routes

• 1-hexadecanoyl-2-octadecanoyl-sn-glycero-3-phosphocholineReach from here →
  1. (11Z)-eicosenoyl-CoA hydrolase
  2. long-chain-fatty-acid-CoA ligase (stearate)
  3. octadecanoyl-CoA + 1-hexadecanoyl-sn-glycero-3-phosphocholine = 1-hexadecanoyl-2-octadecanoyl-sn-glycero-3-phosphocholine + CoA

  Catalysed by BAAT, ACOT6, ACOT1, SLC27A2 and 7 morecytosol

• 1-hexadecanoyl-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphocholineReach from here →
  1. (11Z)-eicosenoyl-CoA hydrolase
  2. long-chain-fatty-acid-CoA ligase ((6Z,9Z)-octadecadienoic acid)
  3. (9Z,12Z)-octadecadienoyl-CoA + 1-hexadecanoyl-sn-glycero-3-phosphocholine = 1-hexadecanoyl-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphocholine + CoA

  Catalysed by BAAT, ACOT6, ACOT1, SLC27A2 and 10 morecytosol

• an N-acylsphing-4-enine 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-acylsphing-4-enine + a 1,2-diacyl-sn-glycero-3-phosphoethanolamine = an N-acylsphing-4-enine 1-phosphoethanolamine + a 1,2-diacyl-sn-glycerol

  Catalysed by LPCAT4, LPCAT3, MBOAT1, MBOAT2 and 3 morecytosol

• a 1-O-alkylglycerone 3-phosphateReach from here →
  1. acyl-CoA pool formation and breakdown
  2. Acyl-CoA:glycerone-phosphate O-acyltransferase
  3. alkylglycerone phosphate synthase (acylglycerone-phosphate)

  Catalysed by GNPAT, AGPScytosol, peroxisomeOne of 2 routes

• (9Z,12Z)-octadecadien-1-olReach from here →
  1. (11Z)-eicosenoyl-CoA hydrolase
  2. long-chain-fatty-acid-CoA ligase ((6Z,9Z)-octadecadienoic acid)
  3. (9Z,12Z)-octadecadienoyl-CoA + 2 NADPH + 2 H(+) = (9Z,12Z)-octadecadien-1-ol + 2 NADP(+) + CoA

  Catalysed by BAAT, ACOT6, ACOT1, SLC27A2 and 8 morecytosol

• 3-oxo-(7Z,10Z,13Z,16Z,19Z)-docosapentaenoyl-CoAReach from here →
  1. (11Z)-eicosenoyl-CoA hydrolase
  2. long-chain-fatty-acid-CoA ligase (EPA)
  3. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA + malonyl-CoA + H(+) = 3-oxo-(7Z,10Z,13Z,16Z,19Z)-docosapentaenoyl-CoA + CO2 + CoA

  Catalysed by BAAT, ACOT6, ACOT1, SLC27A2 and 9 morecytosol

• (9Z,12Z,15Z,18Z,21Z)-3-oxotetracosapentaenoyl-CoAReach from here →
  1. (11Z)-eicosenoyl-CoA hydrolase
  2. long-chain-fatty-acid-CoA ligase (DPA)
  3. (7Z,10Z,13Z,16Z,19Z)-docosapentaenoyl-CoA + malonyl-CoA + H(+) = (9Z,12Z,15Z,18Z,21Z)-3-oxotetracosapentaenoyl-CoA + CO2 + CoA

  Catalysed by BAAT, ACOT6, ACOT1, SLC27A2 and 8 morecytosol

• 3-oxooctacosanyol-CoAReach from here →
  1. (11Z)-eicosenoyl-CoA hydrolase
  2. long-chain-fatty-acid-CoA ligase (cerotic acid)
  3. hexacosanoyl-CoA + malonyl-CoA + H(+) = 3-oxooctacosanyol-CoA + CO2 + CoA

  Catalysed by BAAT, ACOT6, ACOT1, SLC27A2 and 9 morecytosol

• 3-oxotetracosanoyl-CoAReach from here →
  1. (11Z)-eicosenoyl-CoA hydrolase
  2. long-chain-fatty-acid-CoA ligase (behenic acid)
  3. very-long-chain 3-oxoacyl-CoA synthase (docosanoyl-CoA)

  Catalysed by BAAT, ACOT6, ACOT1, SLC27A2 and 14 morecytosolOne of 3 routes

• 3-oxohexacosanoyl-CoAReach from here →
  1. (11Z)-eicosenoyl-CoA hydrolase
  2. long-chain-fatty-acid-CoA ligase (lignocerate)
  3. very-long-chain 3-oxoacyl-CoA synthase (malonyl-CoA)

  Catalysed by BAAT, ACOT6, ACOT1, SLC27A2 and 14 morecytosolOne of 3 routes

• 1-hexadecanoyl-2-[(9Z)-hexadec-9-enoyl]-sn-glycero-3-phosphateReach from here →
  1. (11Z)-eicosenoyl-CoA hydrolase
  2. long-chain-fatty-acid-CoA ligase (palmitolate)
  3. 1-hexadecanoyl-sn-glycero-3-phosphate + (9Z)-hexadecenoyl-CoA = 1-hexadecanoyl-2-[(9Z)-hexadec-9-enoyl]-sn-glycero-3-phosphate + CoA

  Catalysed by BAAT, ACOT6, ACOT1, SLC27A2 and 8 morecytosol

• 1-hexadecanoyl-2-(9Z)-hexadecenoyl-sn-glycero-3-phosphoethanolamineReach from here →
  1. (11Z)-eicosenoyl-CoA hydrolase
  2. long-chain-fatty-acid-CoA ligase (palmitolate)
  3. 1-hexadecanoyl-sn-glycero-3-phosphoethanolamine + (9Z)-hexadecenoyl-CoA = 1-hexadecanoyl-2-(9Z)-hexadecenoyl-sn-glycero-3-phosphoethanolamine + CoA

  Catalysed by BAAT, ACOT6, ACOT1, SLC27A2 and 8 morecytosol

• 1-hexadecanoyl-2-(9Z-hexadecenoyl)-sn-glycero-3-phosphocholineReach from here →
  1. (11Z)-eicosenoyl-CoA hydrolase
  2. long-chain-fatty-acid-CoA ligase (palmitolate)
  3. (9Z)-hexadecenoyl-CoA + 1-hexadecanoyl-sn-glycero-3-phosphocholine = 1-hexadecanoyl-2-(9Z-hexadecenoyl)-sn-glycero-3-phosphocholine + CoA

  Catalysed by BAAT, ACOT6, ACOT1, SLC27A2 and 9 morecytosol

• (11Z,14Z)-3-oxoicosa-11,14-dienoyl-CoAReach from here →
  1. (11Z)-eicosenoyl-CoA hydrolase
  2. long-chain-fatty-acid-CoA ligase ((6Z,9Z)-octadecadienoic acid)
  3. (9Z,12Z)-octadecadienoyl-CoA + malonyl-CoA + H(+) = (11Z,14Z)-3-oxoicosa-11,14-dienoyl-CoA + CO2 + CoA

  Catalysed by BAAT, ACOT6, ACOT1, SLC27A2 and 11 morecytosol

• (11Z,14Z,17Z)-3-oxoeicosatrienoyl-CoAReach from here →
  1. (11Z)-eicosenoyl-CoA hydrolase
  2. long-chain-fatty-acid-CoA ligase (linolenate)
  3. (9Z,12Z,15Z)-octadecatrienoyl-CoA + malonyl-CoA + H(+) = (11Z,14Z,17Z)-3-oxoeicosatrienoyl-CoA + CO2 + CoA

  Catalysed by BAAT, ACOT6, ACOT1, SLC27A2 and 11 morecytosol

• 3-oxo-(15Z)-tetracosenoyl-CoAReach from here →
  1. (11Z)-eicosenoyl-CoA hydrolase
  2. long-chain-fatty-acid-CoA ligase (cis-erucic acid)
  3. (13Z)-docosenoyl-CoA + malonyl-CoA + H(+) = 3-oxo-(15Z)-tetracosenoyl-CoA + CO2 + CoA

  Catalysed by BAAT, ACOT6, ACOT1, SLC27A2 and 8 morecytosol

• 2-hydroxyoctadecanoyl-CoAReach from here →
  1. (11Z)-eicosenoyl-CoA hydrolase
  2. long-chain-fatty-acid-CoA ligase (stearate)
  3. octadecanoyl-CoA + 2-oxoglutarate + O2 = 2-hydroxyoctadecanoyl-CoA + succinate + CO2

  Catalysed by BAAT, ACOT6, ACOT1, SLC27A2 and 7 morecytosol

• N-(15Z-tetracosenoyl)-sphinganineReach from here →
  1. (11Z)-eicosenoyl-CoA hydrolase
  2. long-chain-fatty-acid-CoA ligase (nervonic acid)
  3. (15Z)-tetracosenoyl-CoA + sphinganine = N-(15Z-tetracosenoyl)-sphinganine + CoA + H(+)

  Catalysed by BAAT, ACOT6, ACOT1, SLC27A2 and 8 morecytosol

• N-tetracosanoyl-heptadecasphing-4-enineReach from here →
  1. (11Z)-eicosenoyl-CoA hydrolase
  2. long-chain-fatty-acid-CoA ligase (lignocerate)
  3. heptadecasphing-4-enine + tetracosanoyl-CoA = N-tetracosanoyl-heptadecasphing-4-enine + CoA + H(+)

  Catalysed by BAAT, ACOT6, ACOT1, SLC27A2 and 8 morecytosol

• (2E)-hexacosenoyl-CoAReach from here →
  1. (11Z)-eicosenoyl-CoA hydrolase
  2. long-chain-fatty-acid-CoA ligase (cerotic acid)
  3. acyl-CoA oxidase (hexacosanoyl-CoA)

  Catalysed by BAAT, ACOT6, ACOT1, SLC27A2 and 9 morecytosol, peroxisomeOne of 2 routes

• 3-oxo-(6Z,9Z,12Z,15Z,18Z,21Z)-tetracosahexaenoyl-CoAReach from here →
  1. (11Z)-eicosenoyl-CoA hydrolase
  2. long-chain-fatty-acid-CoA ligase (DHA)
  3. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoyl-CoA + malonyl-CoA + H(+) = 3-oxo-(6Z,9Z,12Z,15Z,18Z,21Z)-tetracosahexaenoyl-CoA + CO2 + CoA

  Catalysed by BAAT, ACOT6, ACOT1, SLC27A2 and 8 morecytosol