hexadecanoic acid

Three steps

• N-(9Z-octadecenoyl)glycineReach from here →
  1. Fas180
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. (9Z)-octadecenoyl-CoA + glycine = N-(9Z-octadecenoyl)glycine + CoA + H(+)

  Catalysed by GLYAT, GLYATL2, GLYATL1, GLYATL3cytosol, mitochondrial matrix

• N-(9Z-octadecenoyl)-L-phenylalanineReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. L-phenylalanine + (9Z)-octadecenoate = N-(9Z-octadecenoyl)-L-phenylalanine + H2O

  Catalysed by PM20D1cytosol, extracellular space

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

  Catalysed by PM20D1cytosol, extracellular space

• N-(9Z-octadecenoyl)-L-leucineReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. N-(9Z-octadecenoyl)-L-leucine + H2O = L-leucine + (9Z)-octadecenoate

  Catalysed by PM20D1cytosol, extracellular space

• N-octadecanoylglycineReach from here →
  1. Palmitate:CoA ligase (AMP-forming)
  2. fatty-acyl-CoA synthase (N-C18:0CoA)
  3. octadecanoyl-CoA + glycine = N-octadecanoylglycine + CoA + H(+)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 5 morecytosolOne of 2 routes

• N-(9Z-hexadecenoyl)-glycineReach from here →
  1. Palmitate:CoA ligase (AMP-forming)
  2. palmitoyl-CoA desaturase (N-C16:0CoA -> N-C16:1CoA)
  3. (9Z)-hexadecenoyl-CoA + glycine = N-(9Z-hexadecenoyl)-glycine + CoA + H(+)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 6 morecytosolOne of 2 routes

• (19R,20S)-epoxy-(4Z,7Z,10Z,13Z,16Z)-docosapentaenoateReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoate + reduced [NADPH--hemoprotein reductase] + O2 = (19R,20S)-epoxy-(4Z,7Z,10Z,13Z,16Z)-docosapentaenoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by CYP1A1, CYP1A2, CYP3A4, CYP2C8 and 3 morecytosol, extracellular space

• (19S,20R)-epoxy-(4Z,7Z,10Z,13Z,16Z)-docosapentaenoateReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoate + reduced [NADPH--hemoprotein reductase] + O2 = (19S,20R)-epoxy-(4Z,7Z,10Z,13Z,16Z)-docosapentaenoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by CYP1A1, CYP3A4, CYP2C8, CYP2D6 and 2 morecytosol, extracellular space

• 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

• 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-hydroxyoctanoyl-CoAReach from here →
  1. Palmitate:CoA ligase (AMP-forming)
  2. Beta Oxidation of Long Chain Fatty Acid
  3. octanoyl-CoA + 2-oxoglutarate + O2 = 2-hydroxyoctanoyl-CoA + succinate + CO2

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

• 2-hydroxydecanoyl-CoAReach from here →
  1. Fas180
  2. medium-chain acyl-CoA ligase (decanoic acid)
  3. decanoyl-CoA + 2-oxoglutarate + O2 = 2-hydroxydecanoyl-CoA + succinate + CO2

  Catalysed by ACSM4, ACSM1, ACSM2A, ACSM3 and 3 morecytosol

• 2-hydroxyeicosanoyl-CoAReach from here →
  1. Fas180
  2. long-chain-fatty-acid-CoA ligase (eicosanoate)
  3. eicosanoyl-CoA + 2-oxoglutarate + O2 = 2-hydroxyeicosanoyl-CoA + succinate + CO2

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

• 2-hydroxydodecanoyl-CoAReach from here →
  1. Fas180
  2. long-chain-fatty-acid-CoA ligase (lauric acid)
  3. dodecanoyl-CoA + 2-oxoglutarate + O2 = 2-hydroxydodecanoyl-CoA + succinate + CO2

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

• 2-hydroxytetradecanoyl-CoAReach from here →
  1. Palmitate:CoA ligase (AMP-forming)
  2. Fatty Acid Beta Oxidation (C16->C14), Mitochondrial
  3. tetradecanoyl-CoA + 2-oxoglutarate + O2 = 2-hydroxytetradecanoyl-CoA + succinate + CO2

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

• 11-cis-retinyl tetradecanoateReach from here →
  1. Palmitate:CoA ligase (AMP-forming)
  2. Fatty Acid Beta Oxidation (C16->C14), Mitochondrial
  3. 11-cis-retinol + tetradecanoyl-CoA = 11-cis-retinyl tetradecanoate + CoA

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 8 morecytosol, mitochondrial matrixOne of 2 routes

• 9-cis-retinyl tetradecanoateReach from here →
  1. Palmitate:CoA ligase (AMP-forming)
  2. Fatty Acid Beta Oxidation (C16->C14), Mitochondrial
  3. 9-cis-retinol + tetradecanoyl-CoA = 9-cis-retinyl tetradecanoate + CoA

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

• 13-cis-retinyl tetradecanoateReach from here →
  1. Palmitate:CoA ligase (AMP-forming)
  2. Fatty Acid Beta Oxidation (C16->C14), Mitochondrial
  3. 13-cis-retinol + tetradecanoyl-CoA = 13-cis-retinyl tetradecanoate + CoA

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

• all-trans-retinyl tetradecanoateReach from here →
  1. Palmitate:CoA ligase (AMP-forming)
  2. Fatty Acid Beta Oxidation (C16->C14), Mitochondrial
  3. all-trans-retinol + tetradecanoyl-CoA = all-trans-retinyl tetradecanoate + CoA

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

• tetradecyl tetradecanoateReach from here →
  1. Palmitate:CoA ligase (AMP-forming)
  2. Fatty Acid Beta Oxidation (C16->C14), Mitochondrial
  3. tetradecan-1-ol + tetradecanoyl-CoA = tetradecyl tetradecanoate + CoA

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

• 1-(9Z-octadecenoyl)-2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-phosphateReach from here →
  1. Fas180
  2. long-chain-fatty-acid-CoA ligase (DHA)
  3. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoyl-CoA + 1-(9Z-octadecenoyl)-sn-glycero-3-phosphate = 1-(9Z-octadecenoyl)-2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-phosphate + CoA

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

• N-hexadecanoylglycineReach from here →
  1. Fas180
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. hexadecanoyl-CoA + glycine = N-hexadecanoylglycine + CoA + H(+)

  Catalysed by GLYAT, GLYATL2, GLYATL1, GLYATL3cytosol, mitochondrial matrix

• N-dodecanoylglycineReach from here →
  1. Fas180
  2. long-chain-fatty-acid-CoA ligase (lauric acid)
  3. dodecanoyl-CoA + glycine = N-dodecanoylglycine + CoA + H(+)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 5 morecytosolOne of 2 routes

• N-decanoylglycineReach from here →
  1. Fas180
  2. medium-chain acyl-CoA ligase (decanoic acid)
  3. decanoyl-CoA + glycine = N-decanoylglycine + CoA + H(+)

  Catalysed by ACSM4, ACSM1, ACSM2A, ACSM3 and 3 morecytosolOne of 2 routes

• N-octanoylglycineReach from here →
  1. Palmitate:CoA ligase (AMP-forming)
  2. Beta Oxidation of Long Chain Fatty Acid
  3. octanoyl-CoA + glycine = N-octanoylglycine + CoA + H(+)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 7 morecytosol, mitochondrial matrixOne of 2 routes

• N(1)-(5-phospho-beta-D-ribosyl)glycinamideReach from here →
  1. Fas180
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. 5-phospho-beta-D-ribosylamine + glycine + ATP = N(1)-(5-phospho-beta-D-ribosyl)glycinamide + ADP + phosphate + H(+)

  Catalysed by GLYAT, GLYATL2, GLYATL1, GARTcytosol, mitochondrial matrix

• L-cystine-bis-glycineReach from here →
  1. Fas180
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. L-cystine-bis-glycine + 2 H2O = L-cystine + 2 glycine

  Catalysed by GLYAT, GLYATL2, GLYATL1, DPEP1 and 1 morecytosol, mitochondrial matrix

• an N-octadecanoyl-sphingoid baseReach from here →
  1. Palmitate:CoA ligase (AMP-forming)
  2. fatty-acyl-CoA synthase (N-C18:0CoA)
  3. a sphingoid base + octadecanoyl-CoA = an N-octadecanoyl-sphingoid base + CoA + H(+)

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

• glycyldehydrophenylalanineReach from here →
  1. Fas180
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. glycyldehydrophenylalanine + H2O = 2,3-didehydrophenylalanine + glycine

  Catalysed by GLYAT, GLYATL2, GLYATL1, DPEP1cytosol, mitochondrial matrix

• 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

• an N-(fatty acyl)-glycineReach from here →
  1. Fas180
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. a fatty acyl-CoA + glycine = an N-(fatty acyl)-glycine + CoA + H(+)

  Catalysed by GLYAT, GLYATL2, GLYATL1cytosol, mitochondrial matrix

• 1-(10Z-heptadecenoyl)-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphoethanolamineReach from here →
  1. Fas180
  2. long-chain-fatty-acid-CoA ligase ((6Z,9Z)-octadecadienoic acid)
  3. 1-(10Z-heptadecenoyl)-sn-glycero-3-phosphoethanolamine + (9Z,12Z)-octadecadienoyl-CoA = 1-(10Z-heptadecenoyl)-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphoethanolamine + CoA

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

• N-(9Z,12Z-octadecadienoyl)-glycineReach from here →
  1. Fas180
  2. long-chain-fatty-acid-CoA ligase ((6Z,9Z)-octadecadienoic acid)
  3. (9Z,12Z)-octadecadienoyl-CoA + glycine = N-(9Z,12Z-octadecadienoyl)-glycine + CoA + H(+)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 5 morecytosolOne of 2 routes

• cholesteryl (7Z)-octadecenoateReach from here →
  1. Fas180
  2. carnitine O-palmitoyltransferase ((7Z)-octadecenoyl-CoA)
  3. (7Z)-octadecenoyl-CoA + cholesterol = cholesteryl (7Z)-octadecenoate + CoA

  Catalysed by CPT1A, CPT1C, CPT1B, SOAT1cytosol

• acetylcholineReach from here →
  1. Fas180
  2. Acetyl-CoA:choline O-acetyltransferase
  3. Acetyl-CoA:choline O-acetyltransferase

  Catalysed by CHATcytosol, nucleusOne of 3 routes

• pyruvateReach from here →
  1. Fas180
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. (R)-3-Amino-2-methylpropanoate:pyruvate aminotransferase

  Catalysed by AGXT2cytosol, mitochondrial matrixOne of 20 routes

• CHEBI:15467Reach from here →
  1. Fas180
  2. Acetoacetate:CoA ligase (AMP-forming)
  3. 3-hydroxy-3-methylglutaryl-CoA synthase (acetoacetyl-CoA)

  Catalysed by AACS, HMGCS1cytosolOne of 3 routes

• CHEBI:15570Reach from here →
  1. Fas180
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. transport of D-alanine and glycine (cytosol to extracellular)

  Catalysed by GLYAT, GLYATL2, GLYATL1, SLC3A2 and 1 morecytosol, mitochondrial matrix, extracellular spaceOne of 3 routes

• (S)-malateReach from here →
  1. Fas180
  2. ATP citrate lyase (citrate)
  3. transport of malate and OAA (cytosol to mitochondria)

  Catalysed by ACLYcytosol, mitochondrial matrixOne of 5 routes

• L-leucineReach from here →
  1. Utilized Transport
  2. Carnitine Transport by Atb0
  3. transport of chloride and leucine (cytosol to extracellular)

  Catalysed by SLC6A14endoplasmic reticulum, cytosol, extracellular spaceOne of 23 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

• CHEBI:15611Reach from here →
  1. Fas180
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. S-Adenosyl-L-methionine:glycine N-methyltransferase

  Catalysed by GLYAT, GLYATL2, GLYATL1, GNMTcytosol, mitochondrial matrix

• (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