(9Z)-octadecenoate

Three steps

• 1'-[1-acyl-2-octadecanoyl-sn-glycero-3-phospho],3'-[1-acyl,2-hydroxy-sn-glycero-3-phospho]-glycerolReach from here →
  1. (9Z)-octadecenoate + ATP + CoA = (9Z)-octadecenoyl-CoA + AMP + diphosphate
  2. octadecanoyl-CoA + 2 Fe(II)-[cytochrome b5] + O2 + 2 H(+) = (9Z)-octadecenoyl-CoA + 2 Fe(III)-[cytochrome b5] + 2 H2O
  3. 1',3'-bis-[1-acyl-sn-glycero-3-phospho]-glycerol + octadecanoyl-CoA = 1'-[1-acyl-2-octadecanoyl-sn-glycero-3-phospho],3'-[1-acyl,2-hydroxy-sn-glycero-3-phospho]-glycerol + CoA

  Catalysed by SLC27A2, ACSL3, ACSL1, ACSBG2 and 7 more

• 1'-[1-acyl-2-(9Z,12Z)-octadecadienoyl-sn-glycero-3-phospho],3'-[1-acyl,2-hydroxy-sn-glycero-3-phospho]-glycerolReach from here →
  1. long-chain-fatty-acid-CoA ligase (oleate)
  2. fatty acyl-CoA desaturase (N-C18:1CoA -> N-C18:2CoA)
  3. 1',3'-bis-[1-acyl-sn-glycero-3-phospho]-glycerol + (9Z,12Z)-octadecadienoyl-CoA = 1'-[1-acyl-2-(9Z,12Z)-octadecadienoyl-sn-glycero-3-phospho],3'-[1-acyl,2-hydroxy-sn-glycero-3-phospho]-glycerol + CoA

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

• (12R)-hydroperoxy-(5Z,8Z,10E,14Z)-eicosatetraenoateReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + O2 = (12R)-hydroperoxy-(5Z,8Z,10E,14Z)-eicosatetraenoate

  Catalysed by ALOX12Bcytosol, extracellular space

• 1-acyl-2-octanoyl-sn-glycero-3-phosphoethanolamineReach from here →
  1. long-chain-fatty-acid-CoA ligase (oleate)
  2. Beta Oxidation Fatty Acid
  3. octanoyl-CoA + a 1-acyl-sn-glycero-3-phosphoethanolamine = 1-acyl-2-octanoyl-sn-glycero-3-phosphoethanolamine + CoA

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 7 morecytosol, mitochondrial matrix

• 1-acyl-2-octadecanoyl-sn-glycero-3-phosphoethanolamineReach from here →
  1. (9Z)-octadecenoate + ATP + CoA = (9Z)-octadecenoyl-CoA + AMP + diphosphate
  2. octadecanoyl-CoA + 2 Fe(II)-[cytochrome b5] + O2 + 2 H(+) = (9Z)-octadecenoyl-CoA + 2 Fe(III)-[cytochrome b5] + 2 H2O
  3. a 1-acyl-sn-glycero-3-phosphoethanolamine + octadecanoyl-CoA = 1-acyl-2-octadecanoyl-sn-glycero-3-phosphoethanolamine + CoA

  Catalysed by SLC27A2, ACSL3, ACSL1, ACSBG2 and 7 more

• 1-hexadecanoyl-2-octanoyl-sn-glycero-3-phosphocholineReach from here →
  1. long-chain-fatty-acid-CoA ligase (oleate)
  2. Beta Oxidation Fatty Acid
  3. octanoyl-CoA + 1-hexadecanoyl-sn-glycero-3-phosphocholine = 1-hexadecanoyl-2-octanoyl-sn-glycero-3-phosphocholine + CoA

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 7 morecytosol, mitochondrial matrix

• (8S)-hydroperoxy-(5Z,9E,11Z,14Z)-eicosatetraenoateReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. Arachidonate:oxygen 8-oxidoreductase

  Catalysed by ALOX12cytosol, extracellular spaceOne of 2 routes

• 1-(9Z-octadecenoyl)-glycerolReach from here →
  1. (9Z)-octadecenoate + ATP + CoA = (9Z)-octadecenoyl-CoA + AMP + diphosphate
  2. 1-(9Z-octadecenoyl)-glycerol + (9Z)-octadecenoyl-CoA = 1,2-di-(9Z-octadecenoyl)-glycerol + CoA
  3. 1,2-di-(9Z-octadecenoyl)-glycerol + H2O = 1-(9Z-octadecenoyl)-glycerol + (9Z)-octadecenoate + H(+)

  Catalysed by SLC27A2, ACSL3, ACSL1, ACSBG2 and 11 moreOne of 2 routes

• 1-hexadecanoyl-2-(9Z-octadecenoyl)-sn-glycerolReach from here →
  1. (9Z)-octadecenoate + ATP + CoA = (9Z)-octadecenoyl-CoA + AMP + diphosphate
  2. 1-hexadecanoyl-sn-glycero-3-phosphate + (9Z)-octadecenoyl-CoA = 1-hexadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phosphate + CoA
  3. 1-hexadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phosphate + H2O = 1-hexadecanoyl-2-(9Z-octadecenoyl)-sn-glycerol + phosphate

  Catalysed by SLC27A2, ACSL3, ACSL1, ACSBG2 and 15 more

• 1-octadecanoyl-2-(9Z-octadecenoyl)-sn-glycerolReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. 1-octadecanoyl-2-(9Z-octadecenoyl)-sn-glycerol + H2O = 2-(9Z-octadecenoyl)-glycerol + octadecanoate + H(+)

  Catalysed by ABHD11cytosol, extracellular spaceOne of 2 routes

• a 2,3-diacyl-sn-glycerolReach from here →
  1. long-chain-fatty-acid-CoA ligase (oleate)
  2. acyl-CoA pool formation and breakdown
  3. a 2-acylglycerol + an acyl-CoA = a 2,3-diacyl-sn-glycerol + CoA

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

• 1-hexadecanoyl-sn-glycerolReach from here →
  1. 1-hexadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phospho-(1D-myo-inositol) + H2O = 1-hexadecanoyl-sn-glycero-3-phospho-(1D-myo-inositol) + (9Z)-octadecenoate + H(+)
  2. 1-hexadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phospho-(1D-myo-inositol) + H2O = 1-hexadecanoyl-sn-glycero-3-phospho-(1D-myo-inositol) + (9Z)-octadecenoate + H(+)
  3. 1-hexadecanoyl-sn-glycero-3-phospho-(1D-myo-inositol) + H2O = 1-hexadecanoyl-sn-glycerol + 1D-myo-inositol 1-phosphate + H(+)

  Catalysed by ABHD16A, GDPD2

• 1,2-di-(9Z)-octadecenoyl-3-hexadecanoyl-sn-glycerolReach from here →
  1. (9Z)-octadecenoate + ATP + CoA = (9Z)-octadecenoyl-CoA + AMP + diphosphate
  2. 2-(9Z-octadecenoyl)-glycerol + (9Z)-octadecenoyl-CoA = 1,2-di-(9Z-octadecenoyl)-sn-glycerol + CoA
  3. 1,2-di-(9Z-octadecenoyl)-sn-glycerol + hexadecanoyl-CoA = 1,2-di-(9Z)-octadecenoyl-3-hexadecanoyl-sn-glycerol + CoA

  Catalysed by SLC27A2, ACSL3, ACSL1, ACSBG2 and 8 more

• hexadecyl octadecanoateReach from here →
  1. (9Z)-octadecenoate + ATP + CoA = (9Z)-octadecenoyl-CoA + AMP + diphosphate
  2. octadecanoyl-CoA + 2 Fe(II)-[cytochrome b5] + O2 + 2 H(+) = (9Z)-octadecenoyl-CoA + 2 Fe(III)-[cytochrome b5] + 2 H2O
  3. hexadecan-1-ol + octadecanoyl-CoA = hexadecyl octadecanoate + CoA

  Catalysed by SLC27A2, ACSL3, ACSL1, ACSBG2 and 8 more

• 1-(9Z-octadecenoyl)-sn-glycerolReach from here →
  1. (9Z)-octadecenoate + ATP + CoA = (9Z)-octadecenoyl-CoA + AMP + diphosphate
  2. sn-glycerol 3-phosphate + (9Z)-octadecenoyl-CoA = 1-(9Z-octadecenoyl)-sn-glycero-3-phosphate + CoA
  3. 1-(9Z-octadecenoyl)-sn-glycero-3-phosphate + H2O = 1-(9Z-octadecenoyl)-sn-glycerol + phosphate

  Catalysed by SLC27A2, ACSL3, ACSL1, ACSBG2 and 13 moreOne of 2 routes

• 1-hexadecanoyl-2,3-di-(9Z)-octadecenoyl-sn-glycerolReach from here →
  1. 1,2-di-(9Z-octadecenoyl)-glycerol + (9Z)-octadecenoate + H(+) = 1,2,3-tri-(9Z-octadecenoyl)-glycerol + H2O
  2. 1,2,3-tri-(9Z-octadecenoyl)-glycerol + H2O = 2,3-di-(9Z)-octadecenoyl-sn-glycerol + (9Z)-octadecenoate + H(+)
  3. 1-hexadecanoyl-2,3-di-(9Z)-octadecenoyl-sn-glycerol + 9-hydroxy-octadecanoate = 9-hexadecanoyloxy-octadecanoate + 2,3-di-(9Z)-octadecenoyl-sn-glycerol

  Catalysed by DGAT1, LIPA, PNPLA4, LIPE and 2 moreOne of 2 routes

• 1-(9Z)-octadecenoyl-3-hexadecanoyl-sn-glycerolReach from here →
  1. (9Z)-octadecenoate + ATP + CoA = (9Z)-octadecenoyl-CoA + AMP + diphosphate
  2. 1-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine + (9Z)-octadecenoyl-CoA = 1,2-di-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine + CoA
  3. 3-hexadecanoyl-sn-glycerol + 1,2-di-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine = 1-(9Z)-octadecenoyl-3-hexadecanoyl-sn-glycerol + (9Z-octadecenoyl)-sn-glycero-3-phosphocholine

  Catalysed by SLC27A2, ACSL3, ACSL1, ACSBG2 and 7 more

• 1-hexadecanoyl-3-(9Z)-octadecenoyl-sn-glycerolReach from here →
  1. (9Z)-octadecenoate + ATP + CoA = (9Z)-octadecenoyl-CoA + AMP + diphosphate
  2. 1-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine + (9Z)-octadecenoyl-CoA = 1,2-di-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine + CoA
  3. 1-hexadecanoyl-sn-glycerol + 1,2-di-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine = 1-hexadecanoyl-3-(9Z)-octadecenoyl-sn-glycerol + (9Z-octadecenoyl)-sn-glycero-3-phosphocholine

  Catalysed by SLC27A2, ACSL3, ACSL1, ACSBG2 and 7 more

• 2-O-(5Z,8Z,11Z,14Z)-eicosatetraenylglycerolReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. fatty acid amide hydrolase (arachidonate)

  Catalysed by FAAHcytosol, extracellular space

• (R)-2-hydroxytetracosanoateReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. tetracosanoate + 2 Fe(II)-[cytochrome b5] + O2 + 2 H(+) = (R)-2-hydroxytetracosanoate + 2 Fe(III)-[cytochrome b5] + H2O

  Catalysed by FA2Hcytosol, extracellular space

• (9Z-octadecenoyl)-glycerolReach from here →
  1. (9Z)-octadecenoate + ATP + CoA = (9Z)-octadecenoyl-CoA + AMP + diphosphate
  2. 2-(9Z-octadecenoyl)-glycerol + (9Z)-octadecenoyl-CoA = 1,2-di-(9Z-octadecenoyl)-sn-glycerol + CoA
  3. 1,2-di-(9Z-octadecenoyl)-sn-glycerol + H2O = (9Z-octadecenoyl)-glycerol + (9Z)-octadecenoate + H(+)

  Catalysed by SLC27A2, ACSL3, ACSL1, ACSBG2 and 8 moreOne of 3 routes

• 3-(9Z-octadecenoyl)-sn-glycerolReach from here →
  1. (9Z)-octadecenoate + ATP + CoA = (9Z)-octadecenoyl-CoA + AMP + diphosphate
  2. 1-(9Z-octadecenoyl)-sn-glycerol + (9Z)-octadecenoyl-CoA = 1,3-di-(9Z-octadecenoyl)-glycerol + CoA
  3. 1,3-di-(9Z-octadecenoyl)-glycerol + H2O = 3-(9Z-octadecenoyl)-sn-glycerol + (9Z)-octadecenoate + H(+)

  Catalysed by SLC27A2, ACSL3, ACSL1, ACSBG2 and 7 moreOne of 2 routes

• 1'-[1,2-diacyl-sn-glycero-3-phospho],3'-[1-acyl,2-octanoyl-sn-glycero-3-phospho]-glycerolReach from here →
  1. long-chain-fatty-acid-CoA ligase (oleate)
  2. Beta Oxidation Fatty Acid
  3. 1'-[1,2-diacyl-sn-glycero-3-phospho],3'-[1-acyl-sn-glycero-3-phospho]-glycerol + octanoyl-CoA = 1'-[1,2-diacyl-sn-glycero-3-phospho],3'-[1-acyl,2-octanoyl-sn-glycero-3-phospho]-glycerol + CoA

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 7 morecytosol, mitochondrial matrix

• 1'-[1-acyl-2-octanoyl-sn-glycero-3-phospho],3'-[1-acyl,2-hydroxy-sn-glycero-3-phospho]-glycerolReach from here →
  1. long-chain-fatty-acid-CoA ligase (oleate)
  2. Beta Oxidation Fatty Acid
  3. 1',3'-bis-[1-acyl-sn-glycero-3-phospho]-glycerol + octanoyl-CoA = 1'-[1-acyl-2-octanoyl-sn-glycero-3-phospho],3'-[1-acyl,2-hydroxy-sn-glycero-3-phospho]-glycerol + CoA

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 7 morecytosol, mitochondrial matrix

• 1-(9Z-octadecenoyl)-N-(acetyl)-sphing-4-enineReach from here →
  1. (9Z)-octadecenoate + ATP + CoA = (9Z)-octadecenoyl-CoA + AMP + diphosphate
  2. 1-hexadecanoyl-sn-glycero-3-phosphocholine + (9Z)-octadecenoyl-CoA = 1-hexadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine + CoA
  3. 1-hexadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine + N-(acetyl)-sphing-4-enine = 1-(9Z-octadecenoyl)-N-(acetyl)-sphing-4-enine + 1-hexadecanoyl-sn-glycero-3-phosphocholine

  Catalysed by SLC27A2, ACSL3, ACSL1, ACSBG2 and 10 moreOne of 5 routes

• 1-O-hexadecyl-2-acetyl-3-(9Z)-octadecenoyl-sn-glycerolReach from here →
  1. (9Z)-octadecenoate + ATP + CoA = (9Z)-octadecenoyl-CoA + AMP + diphosphate
  2. 1-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine + (9Z)-octadecenoyl-CoA = 1,2-di-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine + CoA
  3. 1-O-hexadecyl-2-acetyl-sn-glycerol + 1,2-di-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine = 1-O-hexadecyl-2-acetyl-3-(9Z)-octadecenoyl-sn-glycerol + (9Z-octadecenoyl)-sn-glycero-3-phosphocholine

  Catalysed by SLC27A2, ACSL3, ACSL1, ACSBG2 and 7 more

• 1-O-hexadecyl-2-O-methyl-3-(9Z)-octadecenoyl-sn-glycerolReach from here →
  1. (9Z)-octadecenoate + ATP + CoA = (9Z)-octadecenoyl-CoA + AMP + diphosphate
  2. 1-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine + (9Z)-octadecenoyl-CoA = 1,2-di-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine + CoA
  3. 1-O-hexadecyl-2-O-methyl-sn-glycerol + 1,2-di-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine = 1-O-hexadecyl-2-O-methyl-3-(9Z)-octadecenoyl-sn-glycerol + (9Z-octadecenoyl)-sn-glycero-3-phosphocholine

  Catalysed by SLC27A2, ACSL3, ACSL1, ACSBG2 and 7 more

• 1-(9Z)-octadecenoyl-2-hexadecanoylglycerolReach from here →
  1. (9Z)-octadecenoate + ATP + CoA = (9Z)-octadecenoyl-CoA + AMP + diphosphate
  2. 1-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine + (9Z)-octadecenoyl-CoA = 1,2-di-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine + CoA
  3. 2-hexadecanoylglycerol + 1,2-di-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine = 1-(9Z)-octadecenoyl-2-hexadecanoylglycerol + (9Z-octadecenoyl)-sn-glycero-3-phosphocholine

  Catalysed by SLC27A2, ACSL3, ACSL1, ACSBG2 and 7 more

• 2-[(9Z)-octadecenoylamino]ethyl (9Z)-octadecenoateReach from here →
  1. (9Z)-octadecenoate + ATP + CoA = (9Z)-octadecenoyl-CoA + AMP + diphosphate
  2. 1-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine + (9Z)-octadecenoyl-CoA = 1,2-di-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine + CoA
  3. N-(9Z-octadecenoyl) ethanolamine + 1,2-di-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine = 2-[(9Z)-octadecenoylamino]ethyl (9Z)-octadecenoate + (9Z-octadecenoyl)-sn-glycero-3-phosphocholine

  Catalysed by SLC27A2, ACSL3, ACSL1, ACSBG2 and 7 more

• 2-[(5Z,8Z,11Z,14Z)-eicosatetraenoylamino]ethyl (9Z)-octadecenoateReach from here →
  1. (9Z)-octadecenoate + ATP + CoA = (9Z)-octadecenoyl-CoA + AMP + diphosphate
  2. 1-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine + (9Z)-octadecenoyl-CoA = 1,2-di-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine + CoA
  3. N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-ethanolamine + 1,2-di-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine = 2-[(5Z,8Z,11Z,14Z)-eicosatetraenoylamino]ethyl (9Z)-octadecenoate + (9Z-octadecenoyl)-sn-glycero-3-phosphocholine

  Catalysed by SLC27A2, ACSL3, ACSL1, ACSBG2 and 7 more

• 2-(9Z-octadecenoyl)-sn-glycero-3-phosphocholineReach from here →
  1. (9Z)-octadecenoate + ATP + CoA = (9Z)-octadecenoyl-CoA + AMP + diphosphate
  2. 1-hexadecanoyl-sn-glycero-3-phosphocholine + (9Z)-octadecenoyl-CoA = 1-hexadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine + CoA
  3. 1-hexadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine + N-(acetyl)-sphing-4-enine = 1-hexadecanoyl-N-(acetyl)-sphing-4-enine + 2-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine

  Catalysed by SLC27A2, ACSL3, ACSL1, ACSBG2 and 10 moreOne of 7 routes

• 1-octadecanoyl-N-(acetyl)-sphing-4-enineReach from here →
  1. (9Z)-octadecenoate + ATP + CoA = (9Z)-octadecenoyl-CoA + AMP + diphosphate
  2. 1-octadecanoyl-sn-glycero-3-phosphocholine + (9Z)-octadecenoyl-CoA = 1-octadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine + CoA
  3. 1-octadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine + N-(acetyl)-sphing-4-enine = 1-octadecanoyl-N-(acetyl)-sphing-4-enine + 2-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine

  Catalysed by SLC27A2, ACSL3, ACSL1, ACSBG2 and 6 moreOne of 2 routes

• 2-octadecanoyl-sn-glycero-3-phosphocholineReach from here →
  1. (9Z)-octadecenoate + ATP + CoA = (9Z)-octadecenoyl-CoA + AMP + diphosphate
  2. 1-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamine + (9Z)-octadecenoyl-CoA = 1,2-di-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamine + CoA
  3. 1-hexadecanoyl-2-octadecanoyl-sn-glycero-3-phosphocholine + 1,2-di-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamine = 2-octadecanoyl-sn-glycero-3-phosphocholine + N-hexadecanoyl-1,2-di-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamine + H(+)

  Catalysed by SLC27A2, ACSL3, ACSL1, ACSBG2 and 8 more

• 1-hexadecanoyl-N-(acetyl)-sphing-4-enineReach from here →
  1. (9Z)-octadecenoate + ATP + CoA = (9Z)-octadecenoyl-CoA + AMP + diphosphate
  2. 1-hexadecanoyl-sn-glycero-3-phosphocholine + (9Z)-octadecenoyl-CoA = 1-hexadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine + CoA
  3. 1-hexadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine + N-(acetyl)-sphing-4-enine = 1-hexadecanoyl-N-(acetyl)-sphing-4-enine + 2-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine

  Catalysed by SLC27A2, ACSL3, ACSL1, ACSBG2 and 10 moreOne of 2 routes

• 2-hexadecanoyl-sn-glycero-3-phosphocholineReach from here →
  1. (9Z)-octadecenoate + ATP + CoA = (9Z)-octadecenoyl-CoA + AMP + diphosphate
  2. 1-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamine + (9Z)-octadecenoyl-CoA = 1,2-di-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamine + CoA
  3. 1,2-di-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamine + 1,2-dihexadecanoyl-sn-glycero-3-phosphocholine = N-hexadecanoyl-1,2-di-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamine + 2-hexadecanoyl-sn-glycero-3-phosphocholine + H(+)

  Catalysed by SLC27A2, ACSL3, ACSL1, ACSBG2 and 10 moreOne of 2 routes

• 2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphocholineReach from here →
  1. (9Z)-octadecenoate + ATP + CoA = (9Z)-octadecenoyl-CoA + AMP + diphosphate
  2. 1-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamine + (9Z)-octadecenoyl-CoA = 1,2-di-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamine + CoA
  3. 1,2-di-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholine + 1,2-di-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamine = N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-1,2-di-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamine + 2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphocholine + H(+)

  Catalysed by SLC27A2, ACSL3, ACSL1, ACSBG2 and 8 more

• (9Z-octadecenoyl)-sn-glycero-3-phosphocholineReach from here →
  1. (9Z)-octadecenoate + ATP + CoA = (9Z)-octadecenoyl-CoA + AMP + diphosphate
  2. 1-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine + (9Z)-octadecenoyl-CoA = 1,2-di-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine + CoA
  3. 1,2-di-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine + H2O = (9Z-octadecenoyl)-sn-glycero-3-phosphocholine + (9Z)-octadecenoate + H(+)

  Catalysed by SLC27A2, ACSL3, ACSL1, ACSBG2 and 10 moreOne of 11 routes

• 2-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamineReach from here →
  1. (9Z)-octadecenoate + ATP + CoA = (9Z)-octadecenoyl-CoA + AMP + diphosphate
  2. 1-hexadecanoyl-sn-glycero-3-phosphoethanolamine + (9Z)-octadecenoyl-CoA = 1-hexadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamine + CoA
  3. 1-hexadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamine + N-(acetyl)-sphing-4-enine = 2-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamine + 1-hexadecanoyl-N-(acetyl)-sphing-4-enine

  Catalysed by SLC27A2, ACSL3, ACSL1, ACSBG2 and 7 moreOne of 3 routes

• 1-O-alkyl-3-acylglycerolReach from here →
  1. long-chain-fatty-acid-CoA ligase (oleate)
  2. acyl-CoA pool formation and breakdown
  3. 1-O-alkylglycerol + an acyl-CoA = 1-O-alkyl-3-acylglycerol + CoA

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

• docosanedioateReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. Fatty Acid Omega Oxidation by Hydroxylases (C22->C22Dc), Endoplasmatic Reticulum

  Catalysed by CYP4F2, CYP4F3cytosol, extracellular space, endoplasmic reticulum

• dodecanedioyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (oleate)
  2. Transport of octadecenoyl-CoA into Mitochondrial Matrix
  3. Activation of dodecanedioic acid

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 7 morecytosolOne of 4 routes

• decanedioyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (oleate)
  2. Transport of octadecenoyl-CoA into Mitochondrial Matrix
  3. Production of Sebacoylcarnitine

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 7 morecytosolOne of 4 routes

• octanedioyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (oleate)
  2. Transport of octadecenoyl-CoA into Mitochondrial Matrix
  3. Production of Suberylcarnitine

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 7 morecytosolOne of 4 routes

• hexanedioyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (oleate)
  2. Transport of octadecenoyl-CoA into Mitochondrial Matrix
  3. Activation of adipic acid for Formation of Adipoyl Carnitine

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 7 morecytosolOne of 4 routes

• (4Z,7Z,10Z,13Z,16Z)-docosapentaenoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (oleate)
  2. Transport of octadecenoyl-CoA into Mitochondrial Matrix
  3. long-chain-fatty-acid-CoA ligase ((4Z,7Z,10Z,13Z,16Z)-DPA)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 7 morecytosolOne of 8 routes

• (11Z,14Z)-eicosadienoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (oleate)
  2. Transport of octadecenoyl-CoA into Mitochondrial Matrix
  3. long-chain-fatty-acid-CoA ligase ((11Z,14Z)-eicosadienoic acid)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 7 morecytosolOne of 8 routes

• (R)-3-hydroxy-(11Z)-octadecenoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (oleate)
  2. Transport of octadecenoyl-CoA into Mitochondrial Matrix
  3. Production of 3-Hydroxyoctadecenoylcarnitinec

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

• (13Z)-eicosenoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (oleate)
  2. Transport of octadecenoyl-CoA into Mitochondrial Matrix
  3. long-chain-fatty-acid-CoA ligase ((13Z)-eicosenoic acid)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 7 morecytosolOne of 6 routes

• (25R)-cholest-5-ene-3beta,26-diolReach from here →
  1. N-(9Z-octadecenoyl)-sphing-4-enine + H2O = sphing-4-enine + (9Z)-octadecenoate
  2. beta-D-glucosyl-N-(9Z-octadecenoyl)-sphing-4E-enine + cholesterol = N-(9Z-octadecenoyl)-sphing-4-enine + cholesteryl 3-beta-D-glucoside
  3. 2 reduced [adrenodoxin] + cholesterol + O2 + 2 H(+) = (25R)-cholest-5-ene-3beta,26-diol + 2 oxidized [adrenodoxin] + H2O

  Catalysed by ASAH1, ACER2, ACER1, ASAH2 and 4 more

• 24-hydroxytetracosanoateReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. tetracosanoate + reduced [NADPH--hemoprotein reductase] + O2 = 24-hydroxytetracosanoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by CYP4F2, CYP4F3cytosol, extracellular space