dodecanoate

Three steps

• undecanoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (lauric acid)
  2. Lauroyl-CoA hydrolase
  3. medium-chain acyl-CoA ligase (undecylic acid)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 14 morecytosolOne of 3 routes

• N-(9Z-octadecenoyl)-sphing-4-enineReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. N-(9Z-octadecenoyl)-sphing-4-enine + H2O = sphing-4-enine + (9Z)-octadecenoate

  Catalysed by ASAH1, ACER2, ACER1, ASAH2 and 1 morecytosol, extracellular spaceOne of 4 routes

• (14S)-hydroperoxy-(4Z,7Z,10Z,12E,16Z,19Z)-docosahexaenoateReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoate + O2 = (14S)-hydroperoxy-(4Z,7Z,10Z,12E,16Z,19Z)-docosahexaenoate

  Catalysed by ALOX5, ALOX15, ALOX12cytosol, extracellular space

• (5Z,7Z,8Z,10E,14Z,17Z)-12-hydroperoxyeicosapentaenoateReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate + O2 = (5Z,7Z,8Z,10E,14Z,17Z)-12-hydroperoxyeicosapentaenoate

  Catalysed by ALOX12Bcytosol, extracellular space

• 18-hydroxy-(9Z)-octadecenoateReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. (9Z)-octadecenoate + reduced [NADPH--hemoprotein reductase] + O2 = 18-hydroxy-(9Z)-octadecenoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by CYP4A11, CYP4F11cytosol, extracellular space

• an N-acylsphinganine-1-phosphoethanolamineReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. N-acylsphingosine amidohydrolase
  3. an N-acylsphinganine + a 1,2-diacyl-sn-glycero-3-phosphoethanolamine = an N-acylsphinganine-1-phosphoethanolamine + a 1,2-diacyl-sn-glycerol

  Catalysed by ASAH1, ACER2, ACER1, ASAH2 and 3 morecytosol

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

  Catalysed by ABHD12cytosol, extracellular space

• (11R)-hydroxy-(5Z,8Z,12E,14Z)-eicosatetraenoateReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + AH2 + O2 = (11R)-hydroxy-(5Z,8Z,12E,14Z)-eicosatetraenoate + A + H2O

  Catalysed by PTGS2cytosol, extracellular spaceOne of 2 routes

• (15R)-hydroxy-(5Z,8Z,11Z,13E)-eicosatetraenoateReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + AH2 + O2 = (15R)-hydroxy-(5Z,8Z,11Z,13E)-eicosatetraenoate + A + H2O

  Catalysed by PTGS2cytosol, extracellular spaceOne of 2 routes

• (15R)-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoateReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + O2 = (15R)-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoate

  Catalysed by PTGS2cytosol, extracellular space

• 11R-hydroperoxy-(5Z,8Z,12E,14Z)-eicosatetraenoateReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. Arachidonate: oxygen 11-oxidoreductase

  Catalysed by ALOX12cytosol, extracellular spaceOne of 2 routes

• prostaglandin G2Reach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. Arachidonate:oxygen oxidoreductase

  Catalysed by PTGS1, PTGS2cytosol, extracellular space, endoplasmic reticulumOne of 2 routes

• cholesteryl octadecanoateReach 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. octadecanoyl-CoA + cholesterol = cholesteryl octadecanoate + CoA

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

• cholesteryl (5Z,8Z,11Z,14Z)-eicosatetraenoateReach 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. (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA + cholesterol = cholesteryl (5Z,8Z,11Z,14Z)-eicosatetraenoate + CoA

  Catalysed by NAAA, ASAH1, ACER2, ASAH2 and 4 moreOne of 2 routes

• 14-hydroperoxy-(4Z,7Z,10Z,12E,16Z,19Z)-docosahexaenoateReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoate + O2 = 14-hydroperoxy-(4Z,7Z,10Z,12E,16Z,19Z)-docosahexaenoate

  Catalysed by ALOX12Bcytosol, extracellular space

• (12R)-hydroxy-(5Z,8Z,10E,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 = (12R)-hydroxy-(5Z,8Z,10E,14Z)-eicosatetraenoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by CYP2C9cytosol, extracellular space

• sphinga-4E,14Z-dienineReach 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 + 2 Fe(II)-[cytochrome b5] + O2 + 2 H(+) = sphinga-4E,14Z-dienine + 2 Fe(III)-[cytochrome b5] + 2 H2O

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

• 14,15-epoxy-(5Z,8Z,11Z)-eicosatrienoateReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. unspecific monooxygenase (arachidonate)

  Catalysed by CYP1A1, CYP1A2, CYP2E1, CYP3A4 and 23 morecytosol, extracellular spaceOne of 4 routes

• 8,9-epoxy-(5Z,11Z,14Z)-eicosatrienoateReach 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 3 routes

• tetradecanalReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. tetradecanal + NAD(+) + H2O = tetradecanoate + NADH + 2 H(+)

  Catalysed by ALDH3A2cytosol, extracellular space

• cholesteryl (9Z)-hexadecenoateReach 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. (9Z)-hexadecenoyl-CoA + cholesterol = cholesteryl (9Z)-hexadecenoate + CoA

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

• (9Z,12Z,15Z-octadecatrienoyl)-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. (9Z,12Z,15Z)-octadecatrienoyl-CoA + cholesterol = (9Z,12Z,15Z-octadecatrienoyl)-cholesterol + CoA

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

• cholesteryl (8Z,11Z,14Z)-eicosatrienoateReach 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-(8Z,11Z,14Z-eicosatrienoyl)-sn-glycero-3-phosphocholine + cholesterol = cholesteryl (8Z,11Z,14Z)-eicosatrienoate + 1-hexadecanoyl-sn-glycero-3-phosphocholine

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

• 1-heptadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphoserineReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. 1-heptadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphoserine + H2O = 1-heptadecanoyl-sn-glycero-3-phosphoserine + (5Z,8Z,11Z,14Z)-eicosatetraenoate + H(+)

  Catalysed by ABHD16Acytosol, extracellular space

• 1-heptadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholineReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. 1-heptadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholine + H2O = 1-heptadecanoyl-sn-glycero-3-phosphocholine + (5Z,8Z,11Z,14Z)-eicosatetraenoate + H(+)

  Catalysed by ABHD16Acytosol, extracellular space

• 1-heptadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphoethanolamineReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. 1-heptadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphoethanolamine + H2O = 1-heptadecanoyl-sn-glycero-3-phosphoethanolamine + (5Z,8Z,11Z,14Z)-eicosatetraenoate + H(+)

  Catalysed by ABHD16Acytosol, extracellular space

• O-tetradecanoyl-(R)-carnitineReach from here →
  1. long-chain-fatty-acid-CoA ligase (lauric acid)
  2. fatty-acyl-CoA synthase (N-C14:0CoA)
  3. tetradecanoyl-CoA + (R)-carnitine = O-tetradecanoyl-(R)-carnitine + CoA

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

• (5Z)-tetradecenoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (lauric acid)
  2. Lauroyl-CoA hydrolase
  3. long-chain-fatty-acid-CoA ligase (physeteric acid)

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

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

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 12 morecytosol, mitochondrial matrix

• (5Z,8Z,11Z,14Z,17Z-eicosapentaenoyl)-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. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA + cholesterol = (5Z,8Z,11Z,14Z,17Z-eicosapentaenoyl)-cholesterol + CoA

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

• 4beta-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. cholesterol + reduced [NADPH--hemoprotein reductase] + O2 = 4beta-hydroxycholesterol + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

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

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

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

• (2R,6)-dimethylheptanoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (lauric acid)
  2. Lauroyl-CoA hydrolase
  3. acetyl-CoA C-acyltransferase (3-oxo-4(R),8-dimethyl-nonanoyl-CoA)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 11 morecytosol, mitochondrial matrix

• an N(2)-acyl-L-glutamineReach from here →
  1. long-chain-fatty-acid-CoA ligase (lauric acid)
  2. acyl-CoA pool formation and breakdown
  3. an acyl-CoA + L-glutamine = an N(2)-acyl-L-glutamine + CoA + H(+)

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

• (7Z)-hexadecenoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (lauric acid)
  2. Lauroyl-CoA hydrolase
  3. long-chain-fatty-acid-CoA ligase (7-palmitoleic acid)

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

• cholesteryl (5Z,8Z,11Z)-eicosatrienoateReach 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-eicosatrienoyl)-sn-glycero-3-phosphocholine + cholesterol = cholesteryl (5Z,8Z,11Z)-eicosatrienoate + 1-hexadecanoyl-sn-glycero-3-phosphocholine

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

• (6Z,9Z,12Z-octadecatrienoyl)-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-(6Z,9Z,12Z-octadecatrienoyl)-sn-glycero-3-phosphocholine + cholesterol = (6Z,9Z,12Z-octadecatrienoyl)-cholesterol + 1-hexadecanoyl-sn-glycero-3-phosphocholine

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

• cholesteryl (11Z)-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. (11Z)-octadecenoyl-CoA + cholesterol = cholesteryl (11Z)-octadecenoate + CoA

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

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

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

• a 3-oxoacyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (lauric acid)
  2. acyl-CoA pool formation and breakdown
  3. an acyl-CoA + acetyl-CoA = a 3-oxoacyl-CoA + CoA

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

• (12S)-hydroperoxy-(5Z,8Z,10E,14Z,17Z)-eicosapentaenoateReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate + O2 = (12S)-hydroperoxy-(5Z,8Z,10E,14Z,17Z)-eicosapentaenoate

  Catalysed by ALOX12cytosol, extracellular space

• (18R)-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 = (18R)-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by CYP4F8cytosol, extracellular space

• 17R-hydroxy-(4Z,7Z,10Z,13Z,15E,19Z)-docosahexaenoateReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoate + AH2 + O2 = 17R-hydroxy-(4Z,7Z,10Z,13Z,15E,19Z)-docosahexaenoate + A + H2O

  Catalysed by PTGS2cytosol, extracellular space

• 13-hydroxy-(4Z,7Z,10Z,14E,16Z,19Z)-docosahexaenoateReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoate + AH2 + O2 = 13-hydroxy-(4Z,7Z,10Z,14E,16Z,19Z)-docosahexaenoate + A + H2O

  Catalysed by PTGS2cytosol, extracellular space

• (18R)-hydroxy-(5Z,8Z,11Z,14Z,16E)-eicosapentaenoateReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. prostaglandin-endoperoxide synthase (EPA)

  Catalysed by PTGS1, PTGS2cytosol, extracellular spaceOne of 2 routes

• (15R)-hydroxy-(5Z,8Z,11Z,13E,17Z)-eicosapentaenoateReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate + AH2 + O2 = (15R)-hydroxy-(5Z,8Z,11Z,13E,17Z)-eicosapentaenoate + A + H2O

  Catalysed by PTGS2cytosol, extracellular space

• (11R)-hydroxy-(5Z,8Z,12E,14Z,17Z)-eicosapentaenoateReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate + AH2 + O2 = (11R)-hydroxy-(5Z,8Z,12E,14Z,17Z)-eicosapentaenoate + A + H2O

  Catalysed by PTGS2cytosol, extracellular space

• 15-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoateReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + O2 = 15-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoate

  Catalysed by ALOX15Bcytosol, extracellular space

• 5-hydroperoxy-(6E,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + O2 = 5-hydroperoxy-(6E,8Z,11Z,14Z)-eicosatetraenoate

  Catalysed by ALOX15Bcytosol, extracellular space

• 13R-hydroxy-(7Z,10Z,14E,16Z,19Z)-docosapentaenoateReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. (7Z,10Z,13Z,16Z,19Z)-docosapentaenoate + AH2 + O2 = 13R-hydroxy-(7Z,10Z,14E,16Z,19Z)-docosapentaenoate + A + H2O

  Catalysed by PTGS2cytosol, extracellular space