dodecanoate

Three steps

• 8,9-epoxy-(5Z,11Z,14Z,17Z)-eicosatetraenoateReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate + reduced [NADPH--hemoprotein reductase] + O2 = 8,9-epoxy-(5Z,11Z,14Z,17Z)-eicosatetraenoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by CYP2C9cytosol, extracellular space

• 11,12-epoxy-(5Z,8Z,14Z,17Z)-eicosatetraenoateReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate + reduced [NADPH--hemoprotein reductase] + O2 = 11,12-epoxy-(5Z,8Z,14Z,17Z)-eicosatetraenoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by CYP2C8, CYP2C9cytosol, extracellular space

• 14,15-epoxy-(5Z,8Z,11Z,17Z)-eicosatetraenoateReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate + reduced [NADPH--hemoprotein reductase] + O2 = 14,15-epoxy-(5Z,8Z,11Z,17Z)-eicosatetraenoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by CYP2C8, CYP2C9cytosol, extracellular space

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

  Catalysed by CYP1A1, CYP1A2, CYP2E1, CYP3A4 and 22 morecytosol, extracellular spaceOne of 2 routes

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

  Catalysed by CYP1A1, CYP1A2, CYP2E1, CYP3A4 and 22 morecytosol, extracellular spaceOne of 2 routes

• cholesterol sulfateReach 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. cholesterol + 3'-phosphoadenylyl sulfate = cholesterol sulfate + adenosine 3',5'-bisphosphate + H(+)

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

• 13(S)-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + reduced [NADPH--hemoprotein reductase] + O2 = 13(S)-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by CYP2C9cytosol, extracellular space

• 16(R)-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. unspecific monooxygenase (arachidonate)

  Catalysed by CYP1A1, CYP1A2, CYP2E1, CYP3A4 and 22 morecytosol, extracellular space

• (11Z,14Z,17Z-eicosatrienoyl)-cholesterolReach 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-(11Z,14Z,17Z-eicosatrienoyl)-sn-glycero-3-phosphocholine + cholesterol = (11Z,14Z,17Z-eicosatrienoyl)-cholesterol + 1-hexadecanoyl-sn-glycero-3-phosphocholine

  Catalysed by NAAA, ASAH1, ACER2, ASAH2 and 3 more

• 2-hydroxydecanoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (lauric acid)
  2. Fatty Acid Beta Oxidation (C12->C10), Mitochondrial
  3. decanoyl-CoA + 2-oxoglutarate + O2 = 2-hydroxydecanoyl-CoA + succinate + CO2

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 9 morecytosol, mitochondrial matrix

• 2-hydroxytetradecanoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (lauric acid)
  2. fatty-acyl-CoA synthase (N-C14:0CoA)
  3. tetradecanoyl-CoA + 2-oxoglutarate + O2 = 2-hydroxytetradecanoyl-CoA + succinate + CO2

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

• 11-cis-retinyl tetradecanoateReach from here →
  1. long-chain-fatty-acid-CoA ligase (lauric acid)
  2. fatty-acyl-CoA synthase (N-C14:0CoA)
  3. 11-cis-retinol + tetradecanoyl-CoA = 11-cis-retinyl tetradecanoate + CoA

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

• 9-cis-retinyl tetradecanoateReach from here →
  1. long-chain-fatty-acid-CoA ligase (lauric acid)
  2. fatty-acyl-CoA synthase (N-C14:0CoA)
  3. 9-cis-retinol + tetradecanoyl-CoA = 9-cis-retinyl tetradecanoate + CoA

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

• 13-cis-retinyl tetradecanoateReach from here →
  1. long-chain-fatty-acid-CoA ligase (lauric acid)
  2. fatty-acyl-CoA synthase (N-C14:0CoA)
  3. 13-cis-retinol + tetradecanoyl-CoA = 13-cis-retinyl tetradecanoate + CoA

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

• all-trans-retinyl tetradecanoateReach from here →
  1. long-chain-fatty-acid-CoA ligase (lauric acid)
  2. fatty-acyl-CoA synthase (N-C14:0CoA)
  3. all-trans-retinol + tetradecanoyl-CoA = all-trans-retinyl tetradecanoate + CoA

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

• tetradecyl tetradecanoateReach from here →
  1. long-chain-fatty-acid-CoA ligase (lauric acid)
  2. fatty-acyl-CoA synthase (N-C14:0CoA)
  3. tetradecan-1-ol + tetradecanoyl-CoA = tetradecyl tetradecanoate + CoA

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

• N-decanoylglycineReach from here →
  1. long-chain-fatty-acid-CoA ligase (lauric acid)
  2. Fatty Acid Beta Oxidation (C12->C10), Mitochondrial
  3. decanoyl-CoA + glycine = N-decanoylglycine + CoA + H(+)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 9 morecytosol, mitochondrial matrix

• N-dodecanoyl-(2S)-hydroxyglycineReach 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

• 8-hydroperoxy-(5Z,9E,11Z,14Z)-eicosatetraenoateReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. arachidonate to 8-peroxy-(5Z,9E,11Z,14Z)-eicosatetraenoate conversion

  No catalyst recordedcytosol, extracellular spaceOne of 2 routes

• 1,2,3-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-glycerolReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. 1,2,3-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-glycerol + H2O = 1,2-di-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-glycerol + (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoate + H(+)

  Catalysed by DAGLBcytosol, extracellular space

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

  Catalysed by FAAH, PM20D1cytosol, extracellular space

• cholesteryl (7Z)-octadecenoateReach 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. (7Z)-octadecenoyl-CoA + cholesterol = cholesteryl (7Z)-octadecenoate + CoA

  Catalysed by NAAA, ASAH1, ACER2, ASAH2 and 3 more

• (7Z)-octadecenoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (lauric acid)
  2. Lauroyl-CoA hydrolase
  3. carnitine O-palmitoyltransferase ((7Z)-octadecenoyl-CoA)

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

• CHEBI:15345Reach from here →
  1. long-chain-fatty-acid-CoA ligase (lauric acid)
  2. Lauroyl-CoA hydrolase
  3. Acetoacetate:CoA ligase (AMP-forming)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 9 morecytosolOne of 2 routes

• cholineReach from here →
  1. long-chain-fatty-acid-CoA ligase (lauric acid)
  2. Lauroyl-CoA hydrolase
  3. Acetyl-CoA:choline O-acetyltransferase

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 9 morecytosol, nucleus

• CHEBI:15380Reach from here →
  1. long-chain-fatty-acid-CoA ligase (lauric acid)
  2. Lauroyl-CoA hydrolase
  3. 5-aminolevulinate synthase (2-amino-3-oxoadipate)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 10 morecytosol, mitochondrial matrixOne of 8 routes

• CHEBI:15477Reach from here →
  1. long-chain-fatty-acid-CoA ligase (lauric acid)
  2. Lauroyl-CoA hydrolase
  3. glycine N-acyltransferase (2-methylbutyryl-CoA)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 11 morecytosol, mitochondrial matrixOne of 2 routes

• 2-methylcrotonoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (lauric acid)
  2. Lauroyl-CoA hydrolase
  3. Production of Tiglylcarnitine

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 10 morecytosolOne of 2 routes

• isobutyryl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (lauric acid)
  2. Lauroyl-CoA hydrolase
  3. acetyl-CoA C-acyltransferase (3-oxo-4-methyl-pentanoyl-CoA)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 11 morecytosol, mitochondrial matrixOne of 3 routes

• 3-methylbut-2-enoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (lauric acid)
  2. Lauroyl-CoA hydrolase
  3. glycine-N-acyltransferase (3-methylcrotonoylglycine)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 9 morecytosol, mitochondrial matrix

• isovaleryl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (lauric acid)
  2. Lauroyl-CoA hydrolase
  3. glycine N-acyltransferase (isovalerylglycine)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 11 morecytosol, mitochondrial matrixOne of 3 routes

• arachidonoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (lauric acid)
  2. Lauroyl-CoA hydrolase
  3. Arachidonate:CoA ligase (AMP-forming)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 8 morecytosolOne of 15 routes

• CHEBI:15519Reach from here →
  1. long-chain-fatty-acid-CoA ligase (lauric acid)
  2. Lauroyl-CoA hydrolase
  3. propanoyl-CoA C-acyltransferase

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 11 morecytosol, peroxisomeOne of 2 routes

• palmitoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (lauric acid)
  2. Lauroyl-CoA hydrolase
  3. Palmitate:CoA ligase (AMP-forming)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 8 morecytosolOne of 16 routes

• oleoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (lauric acid)
  2. Lauroyl-CoA hydrolase
  3. Transport of octadecenoyl-CoA into Mitochondrial Matrix

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 11 morecytosolOne of 15 routes

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

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 8 morecytosolOne of 3 routes

• propionyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (lauric acid)
  2. Lauroyl-CoA hydrolase
  3. Propanoate:CoA ligase (AMP-forming)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 11 morecytosolOne of 43 routes

• (7S)-hydroperoxy-(4Z,8E,10Z,13Z,16Z,19Z)-docosahexaenoateReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoate + O2 = (7S)-hydroperoxy-(4Z,8E,10Z,13Z,16Z,19Z)-docosahexaenoate

  Catalysed by ALOX5cytosol, extracellular space

• (11S)-hydroperoxy-(4Z,7Z,9E,13Z,16Z,19Z)-docosahexaenoateReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoate + O2 = (11S)-hydroperoxy-(4Z,7Z,9E,13Z,16Z,19Z)-docosahexaenoate

  Catalysed by ALOX15cytosol, extracellular space

• 12(S)-HPETEReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. arachidonate:oxygen 12-oxidoreductase

  Catalysed by ALOX12cytosol, extracellular spaceOne of 4 routes

• 15(S)-HPETEReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. arachidonate:oxygen 15-oxidoreductase

  Catalysed by ALOX15B, ALOX15cytosol, extracellular spaceOne of 4 routes

• 5(S)-HPETEReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. Arachidonate:oxygen 5-oxidoreductase

  Catalysed by ALOX5cytosol, extracellular space

• CHEBI:15650Reach from here →
  1. long-chain-fatty-acid-CoA ligase (lauric acid)
  2. Lauroyl-CoA hydrolase
  3. N-acetyl-LTE4 to leukotriene E4 conversion

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 40 morecytosolOne of 2 routes

• CHEBI:15727Reach from here →
  1. long-chain-fatty-acid-CoA ligase (lauric acid)
  2. Lauroyl-CoA hydrolase
  3. N-alpha-acetyltransferase 10, NatA catalytic subunit (acetylcarnosine)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 9 morecytosol

• CHEBI:15746Reach from here →
  1. long-chain-fatty-acid-CoA ligase (lauric acid)
  2. Lauroyl-CoA hydrolase
  3. diamine N-acetyltransferase (N1-acetylspermine)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 10 morecytosolOne of 2 routes

• 1-acylglycerone 3-phosphateReach from here →
  1. long-chain-fatty-acid-CoA ligase (lauric acid)
  2. acyl-CoA pool formation and breakdown
  3. Acyl-CoA:glycerone-phosphate O-acyltransferase

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

• phosphatidylethanolamineReach from here →
  1. long-chain-fatty-acid-CoA ligase (lauric acid)
  2. acyl-CoA pool formation and breakdown
  3. Acyl-CoA:1-acyl-sn-glycero-3-phosphoethanolamine O-acyltransferase

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 9 morecytosol

• 1,2-diacyl-sn-glycero-3-phosphocholine(1+)Reach from here →
  1. long-chain-fatty-acid-CoA ligase (lauric acid)
  2. acyl-CoA pool formation and breakdown
  3. Acyl-CoA:1-acyl-sn-glycero-3-phosphocholine O-acyltransferase

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

• 11-cis-retinyl hexadecanoateReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. 11-peroxy-docosahexaenoate to DHA conversion

  No catalyst recordedcytosol, extracellular spaceOne of 3 routes

• 11-cis-retinolReach from here →
  1. long-chain-fatty-acid-CoA ligase (lauric acid)
  2. Lauroyl-CoA hydrolase
  3. Palmitoyl-CoA:retinol O-acyltransferase

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 13 morecytosol