tetradecanoate

Three steps

• 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

• 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

• 2-hydroxydodecanoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (myristic acid)
  2. Fatty Acid Beta Oxidation (C14->C12), Mitochondrial
  3. dodecanoyl-CoA + 2-oxoglutarate + O2 = 2-hydroxydodecanoyl-CoA + succinate + CO2

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

• N-dodecanoylglycineReach from here →
  1. long-chain-fatty-acid-CoA ligase (myristic acid)
  2. Fatty Acid Beta Oxidation (C14->C12), Mitochondrial
  3. dodecanoyl-CoA + glycine = N-dodecanoylglycine + CoA + H(+)

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

• N-tetradecanoyl-(2S)-hydroxyglycineReach from here →
  1. long-chain-fatty-acid-CoA ligase (myristic acid)
  2. tetradecanoyl-CoA + glycine = N-tetradecanoylglycine + CoA + H(+)
  3. N-tetradecanoylglycine + 2 L-ascorbate + O2 = N-tetradecanoyl-(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

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

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 12 morecytosolOne of 4 routes

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

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

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

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

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

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 11 morecytosol, mitochondrial matrixOne of 8 routes

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

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 12 morecytosol, mitochondrial matrixOne of 2 routes

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

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

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

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 12 morecytosol, mitochondrial matrixOne of 3 routes

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

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

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

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 12 morecytosol, mitochondrial matrixOne of 3 routes

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

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 9 morecytosolOne of 15 routes

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

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 12 morecytosol, peroxisomeOne of 2 routes

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

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 12 morecytosolOne of 15 routes

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

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 9 morecytosolOne of 3 routes

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

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 12 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 (myristic acid)
  2. Myristoyl-CoA hydrolase
  3. N-acetyl-LTE4 to leukotriene E4 conversion

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 41 morecytosolOne of 2 routes

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

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

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

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

• 1-acylglycerone 3-phosphateReach from here →
  1. long-chain-fatty-acid-CoA ligase (myristic 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 (myristic 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 (myristic 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

• hexadecan-1-olReach from here →
  1. long-chain-fatty-acid-CoA ligase (myristic acid)
  2. fatty-acyl-CoA synthase (N-C16:0CoA)
  3. formate dehydrogenase (palmitoyl-CoA)

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

• 11-cis-retinyl hexadecanoateReach from here →
  1. long-chain-fatty-acid-CoA ligase (myristic acid)
  2. fatty-acyl-CoA synthase (N-C16:0CoA)
  3. Palmitoyl-CoA:retinol O-acyltransferase

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

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

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 14 morecytosol

• phosphatidic acidReach from here →
  1. long-chain-fatty-acid-CoA ligase (myristic acid)
  2. acyl-CoA pool formation and breakdown
  3. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 13 morecytosol, mitochondrial matrixOne of 7 routes

• (R)-carnitineReach from here →
  1. long-chain-fatty-acid-CoA ligase (myristic acid)
  2. tetradecanoyl-CoA + (R)-carnitine = O-tetradecanoyl-(R)-carnitine + CoA
  3. tetradecanoyl-CoA + (R)-carnitine = O-tetradecanoyl-(R)-carnitine + CoA

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

• oxaloacetateReach from here →
  1. long-chain-fatty-acid-CoA ligase (myristic acid)
  2. Myristoyl-CoA hydrolase
  3. ATP citrate lyase (citrate)

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

• CHEBI:16566Reach from here →
  1. (10Z)-heptadecenoic acid formation
  2. N-acylsphingosine amidohydrolase
  3. N-acylsphingosine amidohydrolase

  Catalysed by ASAH1, ACER2, ACER1, ASAH2 and 1 morecytosol

• 8-hydroxydodecanoateReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. dodecanoate + reduced [NADPH--hemoprotein reductase] + O2 = 8-hydroxydodecanoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by CYP4Z1cytosol, extracellular space

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

  Catalysed by CYP4Z1cytosol, extracellular space

• 9-hydroxydodecanoateReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. dodecanoate + reduced [NADPH--hemoprotein reductase] + O2 = 9-hydroxydodecanoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by CYP4Z1cytosol, extracellular space

• CHEBI:16856Reach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. transport of arachidonate and GSH (cytosol to extracellular)

  No catalyst recordedcytosol, extracellular spaceOne of 2 routes

• psychosineReach from here →
  1. N-tetradecanoylsphing-4-enine + H2O = sphing-4-enine + tetradecanoate
  2. N-tetradecanoylsphing-4-enine + H2O = sphing-4-enine + tetradecanoate
  3. UDP-alpha-D-galactose:sphingosine 1-beta-galactosyltransferase

  Catalysed by ASAH1, ACER2, ASAH2cytosol

• 1-acyl-sn-glycerol 3-phosphateReach from here →
  1. long-chain-fatty-acid-CoA ligase (myristic acid)
  2. glycerol-3-phosphate 1-O-acyltransferase (myristoyl-CoA)
  3. 1-acylglycerol-3P-LD-TG1 pool (liver tissue) formation

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

• a cholesterol esterReach from here →
  1. long-chain-fatty-acid-CoA ligase (myristic acid)
  2. acyl-CoA pool formation and breakdown
  3. an acyl-CoA + cholesterol = a cholesterol ester + CoA

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

• octadecanalReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. octadecanal + NAD(+) + H2O = octadecanoate + NADH + 2 H(+)

  Catalysed by ALDH3A2cytosol, extracellular space