dodecanoate

Three steps

• (3Z)-dodecenoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (lauric acid)
  2. Lauroyl-CoA hydrolase
  3. acetyl-CoA C-acyltransferase (3-oxomyrist-5-enoyl-CoA)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 11 morecytosol, mitochondrial matrixOne of 5 routes

• a 1,2-diacyl-sn-glycero-3-phosphateReach from here →
  1. long-chain-fatty-acid-CoA ligase (lauric acid)
  2. acyl-CoA pool formation and breakdown
  3. a 1-acyl-sn-glycero-3-phosphate + an acyl-CoA = a 1,2-diacyl-sn-glycero-3-phosphate + CoA

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 17 morecytosol

• (25R)-3alpha,7alpha,12alpha-trihydroxy-5beta-cholestan-26-oyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (lauric acid)
  2. Lauroyl-CoA hydrolase
  3. 3alpha,7alpha,12alpha-trihydroxy-5beta-cholestanoate:CoA ligase (AMP-forming)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 9 morecytosol, endoplasmic reticulumOne of 3 routes

• deoxycholoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (lauric acid)
  2. Lauroyl-CoA hydrolase
  3. cholate-CoA ligase (3alpha,12alpha-dihydroxy-5beta-cholanate)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 9 morecytosolOne of 4 routes

• N-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-glycineReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. N-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-glycine + H2O = (5Z,8Z,11Z,14Z)-eicosatetraenoate + glycine

  Catalysed by FAAH, PM20D1cytosol, extracellular space

• monodehydro-L-ascorbate radicalReach 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 morecytosol

• sphing-4-enine 1-phosphateReach from here →
  1. N-dodecanoylsphing-4-enine + H2O = dodecanoate + sphing-4-enine
  2. H2O[c] + N-dodecanoylsphing-4-enine[c] = lauric acid[c] + sphingosine[c]
  3. sphing-4-enine + ATP = sphing-4-enine 1-phosphate + ADP + H(+)

  Catalysed by NAAA, ASAH1, ACER2, ASAH2 and 2 morecytosol

• (9S)-hydroperoxy-(10E,12Z)-octadecadienoateReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. linoleate:oxygen 9-oxidoreductase

  No catalyst recordedcytosol, extracellular space

• (2E)-tetradecenoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (lauric acid)
  2. fatty-acyl-CoA synthase (N-C14:0CoA)
  3. trans-tetradec-2-enoyl-CoA reductase

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 5 morecytosol, mitochondrial matrixOne of 5 routes

• (2E)-decenoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (lauric acid)
  2. Fatty Acid Beta Oxidation (C12->C10), Mitochondrial
  3. trans-dec-2-enoyl-CoA reductase

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 9 morecytosol, mitochondrial matrixOne of 5 routes

• (2E)-hexadecenoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (lauric acid)
  2. Lauroyl-CoA hydrolase
  3. Carnitine O-Palmitoyltransferase

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 11 morecytosolOne of 6 routes

• (9Z)-hexadecenoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (lauric acid)
  2. Lauroyl-CoA hydrolase
  3. long-chain-fatty-acid-CoA ligase (palmitolate)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 8 morecytosolOne of 17 routes

• a cardiolipinReach from here →
  1. long-chain-fatty-acid-CoA ligase (lauric acid)
  2. acyl-CoA pool formation and breakdown
  3. 1'-[1,2-diacyl-sn-glycero-3-phospho],3'-[1-acyl-sn-glycero-3-phospho]-glycerol + an acyl-CoA = a cardiolipin + CoA

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 5 morecytosol

• 3-hydroxyisovaleryl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (lauric acid)
  2. Lauroyl-CoA hydrolase
  3. (3-Hydroxyisovalerylcoa->3-Hydroxyisovalerylcarnitine)

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

• an all-trans-retinyl esterReach from here →
  1. long-chain-fatty-acid-CoA ligase (lauric acid)
  2. acyl-CoA pool formation and breakdown
  3. all-trans-retinol + an acyl-CoA = an all-trans-retinyl ester + CoA

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

• CHEBI:63544Reach from here →
  1. long-chain-fatty-acid-CoA ligase (lauric acid)
  2. Lauroyl-CoA hydrolase
  3. long-chain-fatty-acid-CoA ligase (adrenic acid)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 8 morecytosolOne of 10 routes

• 18-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. cytochrome P450 (arachidonate)

  Catalysed by CYP4F8cytosol, extracellular space, endoplasmic reticulumOne of 2 routes

• 1-O-hexadecyl-sn-glycero-3-phosphocholineReach from here →
  1. N-dodecanoylsphing-4-enine + H2O = dodecanoate + sphing-4-enine
  2. H2O[c] + N-dodecanoylsphing-4-enine[c] = lauric acid[c] + sphingosine[c]
  3. 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(+)

  Catalysed by NAAA, ASAH1, ACER2, ASAH2 and 1 morecytosol

• a 1,2-diacyl-sn-glycero-3-phosphoethanolamineReach from here →
  1. long-chain-fatty-acid-CoA ligase (lauric acid)
  2. acyl-CoA pool formation and breakdown
  3. a 1-acyl-sn-glycero-3-phosphoethanolamine + an acyl-CoA = a 1,2-diacyl-sn-glycero-3-phosphoethanolamine + CoA

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

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

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

• a 1,2-diacyl-sn-glycero-3-phospho-(1'-sn-glycerol)Reach from here →
  1. long-chain-fatty-acid-CoA ligase (lauric acid)
  2. acyl-CoA pool formation and breakdown
  3. 1-acyl-sn-glycero-3-phospho-(1'-sn-glycerol) + an acyl-CoA = a 1,2-diacyl-sn-glycero-3-phospho-(1'-sn-glycerol) + CoA

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

• hexacosanoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (lauric acid)
  2. Lauroyl-CoA hydrolase
  3. long-chain-fatty-acid-CoA ligase (cerotic acid)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 8 morecytosolOne of 9 routes

• tetracosanoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (lauric acid)
  2. Lauroyl-CoA hydrolase
  3. long-chain-fatty-acid-CoA ligase (lignocerate)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 8 morecytosolOne of 17 routes

• docosanoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (lauric acid)
  2. Lauroyl-CoA hydrolase
  3. long-chain-fatty-acid-CoA ligase (behenic acid)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 8 morecytosolOne of 14 routes

• N-(tetradecanoyl)-sphinganineReach from here →
  1. long-chain-fatty-acid-CoA ligase (lauric acid)
  2. fatty-acyl-CoA synthase (N-C14:0CoA)
  3. sphinganine + tetradecanoyl-CoA = N-(tetradecanoyl)-sphinganine + CoA + H(+)

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

• an N-acylsphinganine-1-phosphocholineReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. N-acylsphingosine amidohydrolase
  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 ASAH1, ACER2, ACER1, ASAH2 and 3 morecytosol

• (22R)-hydroxycholesterolReach from here →
  1. N-dodecanoylsphing-4-enine + H2O = dodecanoate + sphing-4-enine
  2. 1-(beta-D-galactosyl)-N-dodecanoylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-galactoside + N-dodecanoylsphing-4-enine
  3. 2 reduced [adrenodoxin] + cholesterol + O2 + 2 H(+) = (22R)-hydroxycholesterol + 2 oxidized [adrenodoxin] + H2O

  Catalysed by NAAA, ASAH1, ACER2, ASAH2 and 3 moreOne of 2 routes

• 3-oxohexadecasphinganineReach from here →
  1. long-chain-fatty-acid-CoA ligase (lauric acid)
  2. fatty-acyl-CoA synthase (N-C14:0CoA)
  3. tetradecanoyl-CoA + L-serine + H(+) = 3-oxohexadecasphinganine + CO2 + CoA

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

• (2E)-octadecenoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (lauric acid)
  2. Lauroyl-CoA hydrolase
  3. Carnitine O-Palmitoyltransferase

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 11 morecytosolOne of 4 routes

• (6Z,9Z,12Z,15Z)-octadecatetraenoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (lauric acid)
  2. Lauroyl-CoA hydrolase
  3. long-chain-fatty-acid-CoA ligase (stearidonic acid)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 8 morecytosolOne of 9 routes

• 1-tetradecanoyl-sn-glycerol 3-phosphateReach from here →
  1. long-chain-fatty-acid-CoA ligase (lauric acid)
  2. fatty-acyl-CoA synthase (N-C14:0CoA)
  3. glycerol-3-phosphate 1-O-acyltransferase (myristoyl-CoA)

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

• 1-(9Z-octadecenoyl)-sn-glycero-3-phospho-(1'-sn-glycerol)Reach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. 1-(9Z-octadecenoyl)-sn-glycero-3-phospho-(1'-sn-glycerol) + H2O = sn-glycero-3-phospho-(1'-sn-glycerol) + (9Z)-octadecenoate + H(+)

  Catalysed by ABHD12cytosol, extracellular space

• 1-hexadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phospho-(1D-myo-inositol)Reach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. 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(+)

  Catalysed by ABHD16Acytosol, extracellular space

• 1-hexadecanoyl-2-tetradecanoyl-sn-glycero-3-phosphateReach from here →
  1. long-chain-fatty-acid-CoA ligase (lauric acid)
  2. fatty-acyl-CoA synthase (N-C14:0CoA)
  3. 1-hexadecanoyl-sn-glycero-3-phosphate + tetradecanoyl-CoA = 1-hexadecanoyl-2-tetradecanoyl-sn-glycero-3-phosphate + CoA

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 5 morecytosol

• N-tetradecanoylsphing-4-enineReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. N-tetradecanoylsphing-4-enine + H2O = sphing-4-enine + tetradecanoate

  Catalysed by ASAH1, ACER2, ASAH2cytosol, extracellular spaceOne of 2 routes

• N-hexadecanoylsphing-4-enineReach from here →
  1. N-dodecanoylsphing-4-enine + H2O = dodecanoate + sphing-4-enine
  2. H2O[c] + N-dodecanoylsphing-4-enine[c] = lauric acid[c] + sphingosine[c]
  3. sphing-4-enine + hexadecanoyl-CoA = N-hexadecanoylsphing-4-enine + CoA + H(+)

  Catalysed by NAAA, ASAH1, ACER2, ASAH2 and 4 morecytosolOne of 3 routes

• N-octadecanoylsphing-4-enineReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. N-octadecanoylsphing-4-enine + H2O = sphing-4-enine + octadecanoate

  Catalysed by ASAH1, ACER2, ASAH2cytosol, extracellular spaceOne of 4 routes

• N-eicosanoyl-sphing-4-enineReach from here →
  1. N-dodecanoylsphing-4-enine + H2O = dodecanoate + sphing-4-enine
  2. H2O[c] + N-dodecanoylsphing-4-enine[c] = lauric acid[c] + sphingosine[c]
  3. eicosanoyl-CoA + sphing-4-enine = N-eicosanoyl-sphing-4-enine + CoA + H(+)

  Catalysed by NAAA, ASAH1, ACER2, ASAH2 and 2 morecytosol

• N-tetracosanoyl-sphing-4-enineReach from here →
  1. N-dodecanoylsphing-4-enine + H2O = dodecanoate + sphing-4-enine
  2. H2O[c] + N-dodecanoylsphing-4-enine[c] = lauric acid[c] + sphingosine[c]
  3. tetracosanoyl-CoA + sphing-4-enine = N-tetracosanoyl-sphing-4-enine + CoA + H(+)

  Catalysed by NAAA, ASAH1, ACER2, ASAH2 and 1 morecytosol

• 1-hexadecanoyl-sn-glycero-3-phosphocholineReach from here →
  1. N-dodecanoylsphing-4-enine + H2O = dodecanoate + sphing-4-enine
  2. 1-(beta-D-galactosyl)-N-dodecanoylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-galactoside + N-dodecanoylsphing-4-enine
  3. 1-hexadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholine + cholesterol = cholesteryl (5Z,8Z,11Z,14Z)-eicosatetraenoate + 1-hexadecanoyl-sn-glycero-3-phosphocholine

  Catalysed by NAAA, ASAH1, ACER2, ASAH2 and 3 moreOne of 9 routes

• (7Z,10Z,13Z,16Z)-docosatetraenoyl-CoAReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. (7Z,10Z,13Z,16Z)-docosatetraenoate + ATP + CoA = (7Z,10Z,13Z,16Z)-docosatetraenoyl-CoA + AMP + diphosphate

  Catalysed by ACSL4cytosol, extracellular space

• (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (lauric acid)
  2. Lauroyl-CoA hydrolase
  3. long-chain-fatty-acid-CoA ligase (EPA)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 8 morecytosolOne of 13 routes

• (7Z,10Z,13Z,16Z,19Z)-docosapentaenoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (lauric acid)
  2. Lauroyl-CoA hydrolase
  3. long-chain-fatty-acid-CoA ligase (DPA)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 8 morecytosolOne of 9 routes

• (9Z,12Z,15Z)-octadecatrienoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (lauric acid)
  2. Lauroyl-CoA hydrolase
  3. long-chain-fatty-acid-CoA ligase (linolenate)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 8 morecytosolOne of 10 routes

• (13Z)-docosenoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (lauric acid)
  2. Lauroyl-CoA hydrolase
  3. long-chain-fatty-acid-CoA ligase (cis-erucic acid)

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

• (11Z)-eicosenoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (lauric acid)
  2. Lauroyl-CoA hydrolase
  3. long-chain-fatty-acid-CoA ligase (cis-gondoic acid)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 8 morecytosolOne of 10 routes

• (9Z,12Z,15Z,18Z,21Z)-tetracosapentaenoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (lauric acid)
  2. Lauroyl-CoA hydrolase
  3. long-chain-fatty-acid-CoA ligase ((9Z,12Z,15Z,18Z,21Z)-TPA)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 8 morecytosolOne of 6 routes

• (6Z,9Z,12Z,15Z,18Z,21Z)-tetracosahexaenoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (lauric acid)
  2. Lauroyl-CoA hydrolase
  3. long-chain-fatty-acid-CoA ligase ((6Z,9Z,12Z,15Z,18Z,21Z)-THA)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 8 morecytosolOne of 5 routes

• (15Z)-tetracosenoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (lauric acid)
  2. Lauroyl-CoA hydrolase
  3. long-chain-fatty-acid-CoA ligase (nervonic acid)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 8 morecytosolOne of 9 routes

• (17Z)-hexacosenoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (lauric acid)
  2. Lauroyl-CoA hydrolase
  3. long-chain-fatty-acid-CoA ligase (ximenic acid)

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