tetradecanoate

Three steps

• 3-oxotetradecasphinganineReach from here →
  1. long-chain-fatty-acid-CoA ligase (myristic acid)
  2. Fatty Acid Beta Oxidation (C14->C12), Mitochondrial
  3. dodecanoyl-CoA + L-serine + H(+) = 3-oxotetradecasphinganine + CO2 + CoA

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

• 3-oxooctadecanoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (myristic acid)
  2. fatty-acyl-CoA synthase (N-C16:0CoA)
  3. very-long-chain 3-oxoacyl-CoA synthase (malonyl-CoA)

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

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

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

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

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

• 1-dodecanoyl-sn-glycerol 3-phosphateReach from here →
  1. long-chain-fatty-acid-CoA ligase (myristic acid)
  2. Fatty Acid Beta Oxidation (C14->C12), Mitochondrial
  3. glycerol-3-phosphate 1-O-acyltransferase (lauroyl-CoA)

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

• 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

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

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

• N-hexadecanoylsphing-4-enineReach from here →
  1. N-tetradecanoylsphing-4-enine + H2O = sphing-4-enine + tetradecanoate
  2. N-tetradecanoylsphing-4-enine + H2O = sphing-4-enine + tetradecanoate
  3. sphing-4-enine + hexadecanoyl-CoA = N-hexadecanoylsphing-4-enine + CoA + H(+)

  Catalysed by ASAH1, ACER2, ASAH2, CERS6 and 3 moreOne of 2 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 3 routes

• N-eicosanoyl-sphing-4-enineReach from here →
  1. N-tetradecanoylsphing-4-enine + H2O = sphing-4-enine + tetradecanoate
  2. N-tetradecanoylsphing-4-enine + H2O = sphing-4-enine + tetradecanoate
  3. eicosanoyl-CoA + sphing-4-enine = N-eicosanoyl-sphing-4-enine + CoA + H(+)

  Catalysed by ASAH1, ACER2, ASAH2, TLCD3B and 1 more

• N-tetracosanoyl-sphing-4-enineReach from here →
  1. N-tetradecanoylsphing-4-enine + H2O = sphing-4-enine + tetradecanoate
  2. N-tetradecanoylsphing-4-enine + H2O = sphing-4-enine + tetradecanoate
  3. tetracosanoyl-CoA + sphing-4-enine = N-tetracosanoyl-sphing-4-enine + CoA + H(+)

  Catalysed by ASAH1, ACER2, ASAH2, CERS2

• (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 (myristic acid)
  2. Myristoyl-CoA hydrolase
  3. long-chain-fatty-acid-CoA ligase (EPA)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 9 morecytosolOne of 13 routes

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

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

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

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 9 morecytosolOne of 10 routes

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

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 9 morecytosolOne of 7 routes

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

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 9 morecytosolOne of 10 routes

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

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 9 morecytosolOne of 6 routes

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

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 9 morecytosolOne of 5 routes

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

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

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

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 9 morecytosolOne of 7 routes

• (8Z,11Z,14Z)-eicosatrienoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (myristic acid)
  2. Myristoyl-CoA hydrolase
  3. long-chain-fatty-acid-CoA ligase (dihomo-gamma-linolenate)

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

• (8Z,11Z,14Z,17Z)-eicosatetraenoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (myristic acid)
  2. Myristoyl-CoA hydrolase
  3. long-chain-fatty-acid-CoA ligase (omega-3-arachidonic acid)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 9 morecytosolOne of 6 routes

• (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (myristic acid)
  2. Myristoyl-CoA hydrolase
  3. long-chain-fatty-acid-CoA ligase (DHA)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 9 morecytosolOne of 11 routes

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

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 9 morecytosolOne of 7 routes

• (9Z)-heptadecenoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (myristic acid)
  2. Myristoyl-CoA hydrolase
  3. long-chain-fatty-acid-CoA ligase (9-heptadecylenic acid)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 9 morecytosolOne of 6 routes

• (11Z,14Z,17Z)-eicosatrienoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (myristic acid)
  2. Myristoyl-CoA hydrolase
  3. long-chain-fatty-acid-CoA ligase ((11Z,14Z,17Z)-eicosatrienoic acid)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 9 morecytosolOne of 6 routes

• N-(15Z-tetracosenoyl)-sphing-4-enineReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. N-(15Z-tetracosenoyl)-sphing-4-enine + H2O = (15Z)-tetracosenoate + sphing-4-enine

  Catalysed by ACER2, ACER1, ASAH2cytosol, extracellular spaceOne of 2 routes

• N-(tetracosenoyl)-sphing-4-enineReach from here →
  1. N-tetradecanoylsphing-4-enine + H2O = sphing-4-enine + tetradecanoate
  2. N-tetradecanoylsphing-4-enine + H2O = sphing-4-enine + tetradecanoate
  3. tetracosenoyl-CoA + sphing-4-enine = N-(tetracosenoyl)-sphing-4-enine + CoA + H(+)

  Catalysed by ASAH1, ACER2, ASAH2, CERS2

• 1-tetradecanoyl-2-(9Z)-octadecenoyl-sn-glycero-3-phosphateReach from here →
  1. long-chain-fatty-acid-CoA ligase (myristic acid)
  2. glycerol-3-phosphate 1-O-acyltransferase (myristoyl-CoA)
  3. 1-tetradecanoyl-sn-glycerol 3-phosphate + (9Z)-octadecenoyl-CoA = 1-tetradecanoyl-2-(9Z)-octadecenoyl-sn-glycero-3-phosphate + CoA

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

• 1-hexadecanoyl-2-dodecanoyl-sn-glycero-3-phosphocholineReach from here →
  1. long-chain-fatty-acid-CoA ligase (myristic acid)
  2. Fatty Acid Beta Oxidation (C14->C12), Mitochondrial
  3. dodecanoyl-CoA + 1-hexadecanoyl-sn-glycero-3-phosphocholine = 1-hexadecanoyl-2-dodecanoyl-sn-glycero-3-phosphocholine + CoA

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

• 1-(9Z)-octadecenoyl-2-dodecanoyl-sn-glycero-3-phosphateReach from here →
  1. long-chain-fatty-acid-CoA ligase (myristic acid)
  2. Fatty Acid Beta Oxidation (C14->C12), Mitochondrial
  3. 1-(9Z-octadecenoyl)-sn-glycero-3-phosphate + dodecanoyl-CoA = 1-(9Z)-octadecenoyl-2-dodecanoyl-sn-glycero-3-phosphate + CoA

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

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

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 9 morecytosolOne of 7 routes

• (11Z)-octadecenoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (myristic acid)
  2. Myristoyl-CoA hydrolase
  3. Transport of 11-Octadecenoyl Carnitine into the Mitochondrial Matrix

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 12 morecytosolOne of 3 routes

• 1-hexadecanoyl-2-dodecanoyl-sn-glycero-3-phospho-(1D-myo-inositol)Reach from here →
  1. long-chain-fatty-acid-CoA ligase (myristic acid)
  2. Fatty Acid Beta Oxidation (C14->C12), Mitochondrial
  3. 1-hexadecanoyl-sn-glycero-3-phospho-(1D-myo-inositol) + dodecanoyl-CoA = 1-hexadecanoyl-2-dodecanoyl-sn-glycero-3-phospho-(1D-myo-inositol) + CoA

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

• 1'-[1-acyl-2-dodecanoyl-sn-glycero-3-phospho],3'-[1-acyl,2-hydroxy-sn-glycero-3-phospho]-glycerolReach from here →
  1. long-chain-fatty-acid-CoA ligase (myristic acid)
  2. Fatty Acid Beta Oxidation (C14->C12), Mitochondrial
  3. 1',3'-bis-[1-acyl-sn-glycero-3-phospho]-glycerol + dodecanoyl-CoA = 1'-[1-acyl-2-dodecanoyl-sn-glycero-3-phospho],3'-[1-acyl,2-hydroxy-sn-glycero-3-phospho]-glycerol + CoA

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

• 1'-[1,2-diacyl-sn-glycero-3-phospho],3'-[1-acyl,2-dodecanoyl-sn-glycero-3-phospho]-glycerolReach from here →
  1. long-chain-fatty-acid-CoA ligase (myristic acid)
  2. Fatty Acid Beta Oxidation (C14->C12), Mitochondrial
  3. 1'-[1,2-diacyl-sn-glycero-3-phospho],3'-[1-acyl-sn-glycero-3-phospho]-glycerol + dodecanoyl-CoA = 1'-[1,2-diacyl-sn-glycero-3-phospho],3'-[1-acyl,2-dodecanoyl-sn-glycero-3-phospho]-glycerol + CoA

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

• (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

• (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-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 space

• a 2,3-diacyl-sn-glycerolReach from here →
  1. long-chain-fatty-acid-CoA ligase (myristic acid)
  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-tetradecanoyl-sn-glycerolReach from here →
  1. long-chain-fatty-acid-CoA ligase (myristic acid)
  2. glycerol-3-phosphate 1-O-acyltransferase (myristoyl-CoA)
  3. 1-tetradecanoyl-sn-glycerol 3-phosphate + H2O = 1-tetradecanoyl-sn-glycerol + phosphate

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

• 1-dodecanoyl-2-(9Z-octadecenoyl)-glycerolReach from here →
  1. long-chain-fatty-acid-CoA ligase (myristic acid)
  2. Fatty Acid Beta Oxidation (C14->C12), Mitochondrial
  3. 2-(9Z-octadecenoyl)-glycerol + dodecanoyl-CoA = 1-dodecanoyl-2-(9Z-octadecenoyl)-glycerol + CoA

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

• 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

• 1-O-alkyl-3-acylglycerolReach from here →
  1. long-chain-fatty-acid-CoA ligase (myristic acid)
  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 (myristic acid)
  2. Myristoyl-CoA hydrolase
  3. Activation of dodecanedioic acid

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

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

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